EP2892345A1 - Use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles or salts thereof as active substances against abiotic plant stress - Google Patents

Use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles or salts thereof as active substances against abiotic plant stress

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Publication number
EP2892345A1
EP2892345A1 EP13758839.8A EP13758839A EP2892345A1 EP 2892345 A1 EP2892345 A1 EP 2892345A1 EP 13758839 A EP13758839 A EP 13758839A EP 2892345 A1 EP2892345 A1 EP 2892345A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
heterocyclyl
aryl
amino
alkoxy
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.)
Withdrawn
Application number
EP13758839.8A
Other languages
German (de)
French (fr)
Inventor
Jens Frackenpohl
Ines Heinemann
Thomas Müller
Jan Dittgen
Pascal VON KOSKULL-DÖRING
Dirk Schmutzler
Martin Jeffrey Hills
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 CropScience AG
Original Assignee
Bayer CropScience 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 CropScience AG filed Critical Bayer CropScience AG
Priority to EP13758839.8A priority Critical patent/EP2892345A1/en
Publication of EP2892345A1 publication Critical patent/EP2892345A1/en
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
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    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/12—Radicals substituted by oxygen atoms
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    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
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    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
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    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
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    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
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    • C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
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    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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    • C07D277/62—Benzothiazoles
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    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
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    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
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    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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    • C07D401/10—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 carbon chain containing aromatic rings
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Definitions

  • the invention relates to the use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoie and 2-amidobenzothiazoles or their salts as active ingredients for increasing the stress tolerance in plants to abiotic stress, in particular for strengthening the plant growth and / or to increase the plant yield. It is known that certain substituted benzimidazoles as
  • Pesticides used see W094 / 1 1349) and that certain haloalkyl-substituted 2-Amidobenzimidazole can be used as active ingredients against abiotic plant stress (see WO201 1 107504). It is also known that substituted amidobenzimidazoie as pharmaceutical agents (see WO2000029384 and WO2000026192) and cosmetic
  • WO97 / 04771 also describes the pharmaceutical use of predominantly aryl-substituted benzimidazoles, while in WO2000032579 heterocyclyl-substituted benzimidazoles are described.
  • the preparation of heterocyclyl-substituted benzimidazoles and their inhibiting action on enzymes from the family of the poly (ADP-ribose) polymerase is described, for example, in Org. Proc. Res Devel. 2007, 11, 693; J. Med. Chem. 2009, 52, 1619 and J. Med. Chem. 2009, 52, 514, while J. Med. Chem. 2010, 53, 3142 disclose methods of preparation for providing specific aryl-substituted benzimidazoles ,
  • abiotic stress defense reactions e.g., cold, heat, drought, salt, flooding
  • signal transduction chains e.g., transcription factors, kinases, phosphatases
  • the signal chain genes of the abiotic stress reaction include, among others.
  • ROS reactive oxygen species
  • HSF Heat Shock Factors
  • HSP Heat Shock Proteins
  • Substances or their stable synthetic derivatives and derived structures are also effective in external application to plants or seed dressing and activate defense reactions that result in an increased stress or pathogen tolerance of the plant [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589].
  • osmolytes e.g. Glycine betaine or its biochemical precursors, e.g. Choline derivatives have been observed (Chen et al., 2000, Plant Cell Environ 23: 609-618, Bergmann et al., DE-4103253).
  • the action of antioxidants such as naphtols and xanthines to increase the abiotic stress tolerance in plants has also been described (Bergmann et al., DD-277832, Bergmann et al., DD-277835).
  • the molecular causes of the anti-stress effects of these substances are largely unknown.
  • PARP poly-ADP-ribose polymerases
  • PARG poly (ADP-ribose) glycohydrolases
  • the object of the present invention was to provide further compounds which increase the tolerance to abiotic stress in plants.
  • the present invention accordingly provides for the use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles
  • R 1 , R 2 , R 3 independently of one another represent hydrogen, halogen, alkyl, cycloalkyl,
  • R 1 and R 2 with the atoms to which they are attached form a completely saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring,
  • R 2 and R 3 with the atoms to which they are attached, a fully saturated, form part-saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring,
  • W stands for oxygen, sulfur,
  • X is oxygen, sulfur, NR 4 ,
  • R 4 is hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cyanoalkyl,
  • Q is alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, aryl, arylalkyl,
  • heteroarylalkyl heterocyclylalkyl, heteroaryl, heterocyclyl, heterocyclylaryl, heterocyclylheteroaryl, heteroarylheteroaryl, heteroarylaryl, arylaryl,
  • Arylalkylaminocarbonyl aminocarbonyl, alkylaminocarbonyl,
  • Cycloalkylaminocarbonyl bis-alkylaminocarbonyl, heterocyclyl-N-carbonyl, imino, alkylimino, arylimino, cycloalkylimino, cycloalkylalkylimino,
  • Cycloalkylaminoalkyl alkoxy (alkoxy) alkyl, arylalkoxyalkylaryl, heterocyclyl-N-alkylaryl, aryl (alkyl) aminoalkylaryl, arylalkyl (alkyl) aminoalkylaryl,
  • Alkoxycarbonylalkylaminoalkylaryl alkoxycarbonylalkyl (alkyl) aminoalkylaryl, heteroaryl (alkyl) aminoalkylaryl, heteroarylalkyl (alkyl) aminoalkylaryl,
  • Z 2 is hydrogen, alkyl, cycloalkyl, branched or unbranched haloalkyl, aikinyl, alkenyl, cyanoalkyl, arylalkyl, heteroarylalkyl, alkylcarbonyl,
  • Alkoxycarbonyl is or
  • Z 1 and Z 2 together are part of an optionally substituted Sulfilimin- or amidine group or form a iminophosphorane.
  • the compounds of general formula (I) may be prepared by addition of a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3, or organic acids, e.g.
  • a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3, or organic acids, e.g.
  • 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.
  • Cycloalkyl (-, the inventive use of compounds of general formula (I) wherein R 1, R 2, R 3 are independently hydrogen, halogen, (Ci-C 8) -alkyl, (C 3 -C 8) is preferably C 4 -C 8) cycloalkenyl, (C 3 -C 8) halocycloalkyl, (C 2 -C 8) alkenyl, (C2-C8) -alkynyl, optionally substituted phenyl, aryl (Ci-C 8) -alkyl, aryl- (C 2 -C 8 ) -alkenyl, heteroaryl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (Ci -C 8) alkyl, (dC 8) alkylthio, (Ci-C
  • Cycloalkoxy (C 3 -C 8) cycloalkyl (Ci-C8) alkoxy, aryloxy, Heteroraryloxy,
  • R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • interrupted and optionally further substituted 5 to 7-membered ring represents oxygen, sulfur,
  • X represents oxygen, sulfur, NR 4, represents hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) cycloalkyl (Ci-C8) - alkyl , (C 4 -C 8) cycloalkenyl, cyano (Ci-C 8) alkyl, (C 2 -C 8) alkenyl (Ci-C 8) alkyl, (Ci-C 8) haloalkyl, (C 2 -C 8) alkynyl (Ci-C 8) alkyl, aryl (Ci-C 8) alkyl, heteroaryl (dC 8) alkyl, heterocyclyl (Ci-C8) alkyl, (Ci-C 8) alkylcarbonyl, (C 3 -C 8) - cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (Ci-C 8)
  • Z 2 is hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) -Cyc Oalkyl, (Ci-C8) -haloalkyl, (C 2 -C 8) - alkynyl, (C 2 -C 8 ) alkenyl, cyano (Ci-C 8 ) alkyl, aryl (Ci-C 8 ) alkyl, heteroaryl (Ci-Cs) alkyl, (Ci-C 8 ) alkylcarbonyl, (Ci-C 8 ) alkoxycarbonyl or
  • Z 1 and Z 2 together form a N- (bis (Ci-C8) alkyl) sulfanyliden-, N- (aryl (dC 8) - alkyl) sulfanyliden-, N- (bis- (C 3 -C 8 ) -Cycloalkyl) sulfanylidene, N - ((C 1 -C 8 ) -alkyl
  • R 1 , R 2 , R 3 independently of one another represent hydrogen, iodine, bromine, chlorine, fluorine, (C 1 -C 7 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, ( C 3 -C 7 ) -halocycloalkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, optionally substituted phenyl, aryl- (C 1 -C 4) -alkyl, aryl- (C 2 -C) -alkenyl , Heteroaryl, heteroaryl (Ci-C /) - alkyl, heterocyclyl,
  • Alkylamino bis - [(Ci-C 7 ) -alkyl] amino, (Ci-C 7 ) - Aikylcarbonylamino, (C3-C7) - Cycloalkyicarbonylamino, Arylcarbonylamino, (Ci-C) -Aikoxycarbonylamino, Heterocyclyi- (Ci-C 7 ) -alkoxy, (C 3 -C 7 ) -cycloalkyl-(C 1 -C 4 ) -alkyl, (C 2 -C 7 ) -hioacylic, (C 2 -C 6) -haloalkynyl, heterocyciyl- (C 2 -) C /) alkynyl, (C3-C7) halocycloalkoxy, (C 2 -C) -haloalkylinyloxy, arylthio, heteroaryithio, (C 1 -C
  • R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • W stands for oxygen, sulfur,
  • X is oxygen, sulfur, NR 4, R 4 is hydrogen, (dC /) - alkyl, (C 3 -C 7) -cycloalkyl, (C 3 -C 7) cycloalkyl (Ci-C7) - alkyl , (C 4 -C 7) cycloalkenyl, cyano (Ci-C /) - alkyl, (C 2 -C 7) alkenyl (Ci-C7) alkyl, (Ci-C7) haloalkyl, (C 2 -C 6) -alkynyl- (C 1 -C 4) -alkyl, aryl- (C 1 -C 4) -alkyl, heteroaryl- (C 1 -C 6) -alkyl, heterocyclyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylcarbonyl, (C 3 -C 7 ) -cycl
  • heterocyclyl heterocyclylaryl, heterocyclylheteroaryl, heteroarylheteroaryl, heteroarylaryl, arylaryl, aryloxyaryl, aryl- (C 2 -C 7 ) -alkenyl, heteroaryl- (C 2 -C) -alkenyl, heterocyclyl- (C 2 -C 7 ) -alkenyl, aryl- (C 2 -C /) - alkynyl, heteroaryl (C 2 -C 7) - alkynyl, heterocyclyl (Ci-C7) alkynyl, (C 3 -C /) - cycloalkyl- (C 2 -C 7) -alkynyl, ( C1-C7) -alkylamino- (C 1 -C 7 ) -alkyl, bis- [(C 1 -C 4) -alkyl] amino- (C 1 -C 4)
  • Z 1 represents hydrogen, hydroxy, (C 1 -C 4 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -
  • Halocycloalkyl bromine, chlorine, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 7 ) -alkynyl, (C 2 -C / ) Alkenyl, cyano- (Ci-C /) - alkyl, nitro (Ci-C /) - alkyl, amino- (Ci-C /) - alkyl, alkyl- (Ci-C 7 ) -amino- (Ci -C 7) alkyl, - bis [(Ci-C) alkyl] amino- (Ci-C7) alkyl, (C 2 -C 7) alkynyl (Ci-C7) alkyl, aryl (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 4 ) -
  • Z 2 is hydrogen, (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 7 ) -alkynyl, (C 2 -C /) Alkenyl, cyano- (Ci-C /) - alkyl, aryl- (Ci-C 7 ) -alkyl, heteroaryl- (Ci-C 7 ) -alkyl, (Ci-C /) - alkylcarbonyl, (Ci-C 7 ) Alkoxycarbonyl or
  • R 1 , R 3 and R 3 independently of one another represent hydrogen, iodine, bromine, chlorine, fluorine, (C 1 -C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 3 -C 6 ) -halocycloalkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, optionally substituted phenyl, aryl- (C 1 -C 4 ) -alkyl, aryl- (C 2 -C 4 ) -alkenyl, Heteroaryl, heteroaryl- (C 1 -C 4) -alkyl, heterocyclyl,
  • R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • X is oxygen, sulfur, NR 4 ,
  • R 4 represents hydrogen, (Ci-C 4) -alkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci-C4) - alkyl, (C 4 -C 6) cycloalkenyl, cyano (Ci-C 4) alkyl, (C2-C4) alkenyl (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 2 -C) alkynyl ( C 1 -C 4 ) -alkyl, aryl- (C 1 -C 4 ) -alkyl, heteroaryl- (C 1 -C 4 ) -alkyl, heterocyclyl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylcarbonyl, ( C 3 -C 6) - cycloalkylcarbonyl, arylcarbon
  • Q is (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -alkenyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 4 -C 6) cycloalkenyl, optionally substituted phenyl, aryl- (Ci-C4) - alkyl, heteroaryl (Ci-C) alkyl, heterocyclyl (Ci-C 4) alkyl, heteroaryl,
  • Heterocyclyl (Ci-C 4) alkyl, (dC 4) alkylcarbonyl, (Ci-C 4) alkoxycarbonyl, (C 3 -C 6) cycloalkoxycarbonyl, (Ci-C 4) alkylsulfonyl, arylsulfonyl,
  • Residue definitions apply both to the end products of the formula (I) and
  • R ⁇ R 2 , R 3 independently of one another represent hydrogen, halogen, (C 1 -C 6 -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C 3 -C 8 ) -halocycloalkyl , (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, optionally substituted phenyl, aryl- (C 1 -C 8 ) -alkyl, aryl- (C 2 -C 8 ) -alkenyl, heteroaryl, heteroaryl- C 1 -C 8 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8
  • R 1 and R 2 with the atoms to which they are attached form a completely saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring, R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • W is oxygen, sulfur, X is oxygen, sulfur is,
  • Q is (Ci-C 8) haloalkyl, (Ci-C 8) alkoxy (Ci-C8) -haloalkyl, (C 3 -C 8) halocycloalkyl, (Ci-C8) haloalkoxy (dC 8 ) -haloalkyl, aryl- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -haloalkyl, bis [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 4) -alkyl C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl,
  • Z 1 is hydrogen, hydroxy, (C 1 -C 5 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -
  • Z 2 is hydrogen, (DC 8) alkyl, (C 3 -C 8) cycloalkyl, (DC 8) -haloalkyl, (C 2 -C 8) - alkynyl, (C 2 -C 8) alkenyl, cyano - (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, (C 1 -C 8 ) -alkoxycarbonyl or
  • R ⁇ R 2, R 3 are independently hydrogen, halogen, (Ci-C 4) -alkyl, (C 3 -C 8) - cycloalkyl, (C 4 -C 8) cycloalkenyl, (C 3 -C 8) -Halocycloalkyl, (C 2 -C 4 ) -alkenyl,
  • (C 2 -C 4 ) -alkynyl optionally substituted phenyl, aryl- (C 1 -C 4 ) -alkyl, aryl- (C 2 -C 5) -alkenyl, heteroaryl, heteroaryl- (C 1 -C 4 ) -alkyl, heterocyclyl, heterocyclyl -
  • R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • W is oxygen, sulfur, X is oxygen, sulfur, Q is (Ci-C /) - haloalkyl, (Ci-C 4) alkoxy (Ci-C 4) -haloalkyl, (C 3 -C 8) halocycloalkyl,
  • Z 1 represents hydrogen, hydroxy, (Ci-C 4) -alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) - halocycloalkyl, halogen, (C2-C4) alkenyl (Ci C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl,
  • Z 2 is hydrogen, (Ci-C 4) -alkyl, (C 3 -C 8) -Cyc Oalkyl, (Ci-C 4) -haloalkyl, (C2-C4) - alkynyl, (C2-C4) - Alkenyl, cyano- (C 1 -C 4 ) -alkyl, aryl- (C 1 -C 4 ) -alkyl, heteroaryl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 4 ) Alkoxycarbonyl or
  • Z 1 and Z 2 together form a N- (bis (C 1 -C 6 ) alkyl) sulfanylidene, N- (aryl- (C 1 -C 6 ) -alkyl) sulfanylidene, N- (bis (C 3 -C 7 ) -Cycloalkyl) sulfanylidene, N - ((C 1 -C 6 ) -alkyl-
  • R 2 , R 3 independently of one another represent hydrogen, halogen, (C 1 -C 6 -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C 3 -C 8 ) -halocycsoalkyl, (C 2 -C 8) alkenyl, (C2-C8) -alkynyl, optionally substituted phenyl, aryl (Ci-C8) alkyl, aryl (C2-C8) alkenyl, heteroaryl, heteroaryl (Ci- C8) alkyl, heterocyclyl, heterocyclyl (Ci-C8) alkyl, (Ci-C 8 () alkoxy- Ci-C 8) alkyl, (CrC 8) alkylthio, (Ci-C 8) - haloalkylthio, (Ci-C 8) haloalkyl, (Ci-C
  • R 1 and R 2 contain the atoms they are bonded, form a fully saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring, R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or form unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring, W for oxygen, sulfur! sees
  • X is NR 4 ,
  • R 4 represents hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) -Cyc oa ky -! (Ci-C8) - alkyl, (C 4 -C 8) cycloalkenyl, cyano (Ci-C8) -a! kyl, (C 2 -C 8) alkenyl (Ci-C 8) alkyl, (Ci-C 8) -Ha! oa !
  • kyl (C 2 -C 8) alkynyl (Ci-C 8) alkyl, aryl (Ci-C 8) -alkyS, heteroaryl (Ci-Cs) -a! kyl, heterocyclyl (Ci- C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, (C 3 -C 8 ) -cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C 1 -C 8 ) -haloalkylcarbonyl, heterocyclylcarbonyl, aryl- (C 1 -C 8 ) -alkylcarbonyl , (C 1 -C 8 ) -alkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C
  • Q is (Ci-C 8) alkyl, (C 2 -C 8) -alkenyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) -cycloalkyl- (Ci-C8) - alkyl, (C 4 -C 8 ) -cycloalkenyl, optionally substituted phenyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryi (C 1 -C 8 ) -acyl, heterocyclyl- (C 1 -C 8 ) -alkyl, heteroaryl,
  • heterocyclyl heterocyclylaryl, heterocyclylheteroaryl, heteroarylheteroaryl, heteroarylaryl, arylaryl, aryloxyaryl, aryl- (C 2 -C 8 ) -alkenyl, heteroaryl- (C 2 -C 8 ) -alkenyl, heterocyclyl- (C 2 -C 8 ) -alkenyl, aryl- C2-C8) alkynyl, heteroaryl (C2-C8) - alkynyl, heterocyclyl (Ci-C8) -alkynyl, (C 3 -C 8) -Cycloalky - (C2-C8) -a!
  • Aryloxyheteroaryl (Ci-C8) alkylsulfinyl, (Ci-C 8) - alkylthio, (Ci-C 8) -A kylsulfonyl, (C3-C8) cycloalkylsulfinyl, (C 3 -C 8) -cycloalkylthio , (C 3 -C 8) -cycloalkylsulfonyl, arylsulfinyl, arylthio, arylsulfonyl, amino, (C 1 -C 8 ) -alkylamino, bis - [(C 1 -C 8 ) -alkyl] amino, arylamino, aryl- (C 1 -C 8 ) alkylamino, (C 3 -C 8 ) -cycloalkylamino, formyl, (C 1 -C 8 ) -alkylcarbonyl,
  • Z 1 and Z 2 together form a N- (bis (C 1 -C 8 ) -acyl) sulfanylidene, N- (aryl- (C 1 -C 8 ) -alkyl) sulfanylidene, N- (bis (C 3 -C 8 ) Cycloalkyl) sulfanylidene, N - ((C 1 -C 8 ) alkyl (C 3 -C 8 ) cycloalkyl) sulfanylidene group or an N, N-di (C 1 -C 8) alkylformylidene group.
  • R 1 , R 3 and R 3 independently of one another are hydrogen, halogen, (C 1 -C 4 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C 3 -C 8 ) - Halocycloalkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, optionally substituted phenyl, aryl- (C 1 -C 4 ) -alkyl, aryl- (C 2 -C 4 ) -alkenyl, heteroaryl, heteroaryl- (C 1 -C 4 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C
  • R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • W is oxygen, sulfur, X is NR 4 ,
  • R 4 represents hydrogen, (Ci-C 4) -alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) -cycloalkyl- (Ci-C4) - alkyl, (C4-C8) - cycloalkenyl, cyano (Ci-C 4) alkyl, (C2-C4) alkenyl (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C2-C4) alkynyl (Ci- C 4) alkyl, aryl (Ci-C 4) alkyl, heteroaryl (Ci-C 4) alkyl, heterocyclyl (Ci-C 4) alkyl, (Ci-C 4) alkylcarbonyl, (C 3 -C 8 ) -cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C 1 -C 4 ) -haloalkyl
  • Z 1 and Z 2 together form an N- (bis (C 1 -C 4) alkyl) sulfanylidene, N- (aryl- (C 1 -C 4) -alkyl) sulfanylidene, N- (bis- (C 3 -C 8 ) Cycloalkyl) sulfanylidene, N - ((C 1 -C 4 ) -alkyl- (C 3 -C 8) -cycloalkyl) sulfanylidene group or an N, N-di- (C 1 -C 4 ) -alkylformylidene group.
  • arylsulfonyl is optionally substituted phenylsulfonyl or optionally substituted polycyclic arylsulfonyl, here in particular optionally substituted naphthylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino,
  • Alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups
  • cycloalkylsulfonyl alone or as part of a chemical group - is optionally substituted Cycloalkylsulfonyl, preferably having 3 to 6 carbon atoms such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl.
  • alkylsulfonyl alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably having 1 to 8, or having 1 to 6 carbon atoms such as methylsulfonyl,
  • heteroarylsulfonyl is optionally substituted
  • substituted polycyclic heteroarylsulfonyl here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino,
  • Alkylcarbonylamino, dialkylamino or alkoxy groups Alkylcarbonylamino, dialkylamino or alkoxy groups.
  • alkylthio alone or as part of a chemical group - represents straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n- Butylthio, isobutylthio, sec-butylthio and tert-butylthio.
  • Alkenylthio represents an alkenyl radical bonded via a sulfur atom
  • alkynylthio represents an alkynyl radical bonded via a sulfur atom
  • cycloalkylthio represents a cycloalkyl radical bonded via a sulfur atom
  • cycloalkenylthio represents a cycloalkenyl radical bonded via a sulfur atom
  • Alkoxy means an alkyl radical bonded via an oxygen atom
  • alkenyloxy represents an alkynyl radical bound via an oxygen atom
  • alkynyloxy means an alkynyl radical bound via an oxygen atom
  • cycloalkyloxy denotes a cycloalkyl radical bonded via an oxygen atom
  • cycloalkynyloxy denotes a cycloalkenyl radical bonded via an oxygen atom.
  • aryl means an optionally substituted mono-, bi- or
  • polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • optionally substituted aryl also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, the binding site being on the aromatic system.
  • Aryl is also generally known from the term “optionally substituted phenyl ".
  • Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl,
  • heterocyclic ring preferably contains 3 to 9 ring atoms, especially 3 to 6
  • Ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two oxygen atoms should be directly adjacent, as
  • heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrole-2 or 3-yl, 2,3-dihydro-1 H-pyrrole 1- or 2- or
  • 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-membered and 4-membered 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 having 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-1 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; Hexahydropyridazine-1 - or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazine-1 -
  • 5- or 6-yl 5,6-dihydro-4H-1,2-oxazine-3- or 4- or 5- or 6-yl; 2H-1, 2-oxazine-2 or 3 or 4 or 5 or 6-yl; 6H-1, 2-oxazine-3 or 4 or 5 or 6-yl; 4H-1, 2-oxazine-3 or 4 or 5 or 6-yl; 1,3-oxazinan-2 or 3 or 4 or 5 or 6-yl;
  • 6- or 7-yl 1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; isothiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazole-2- or 3- or 4- or 5-yl; 2,5-dihydroisothiazole-2 or 3 or 4 or 5-yl; 4,5-dihydroisothiazole-3 or 4 or 5-yl; 1,3-thiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydro-1, 3-thiazole-2 or 3 or
  • Heterocycly are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as 1, 4,2-Dioxazo! idin-2- or 3- or 5-yl; 1, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,2,2,2-dioxazine-3- or 5- or 6-yl; 1,2,2-dioxazine-3- or 5- or 6-yl; 1, 4,2-dioxazepan-2 or 3 or 5 or 6 or 7-yl; 6,7-dihydro-5H-1, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 2,3-dihydro-7H-, 4,2-dioxazepin-2 or 3 or 5 or 6 or 7-yl; 2,3-dihydro-5H-1,2,2-dio
  • heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl,
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo.
  • Oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
  • lactones and lactams are preferably also included.
  • the oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. in the case of N and S, for example, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also SO2 for short) occur and form in the heterocyclic ring.
  • N and S for example, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also SO2 for short) occur and form in the heterocyclic ring.
  • -N (O) and -S (O) groups both enantiomers are included.
  • heteroaryl is heteroaromatic
  • Heteroaryls of the invention are, for example, 1H-pyrro-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazole-1-yl; 1 H-imidazol-2-yl; 1 H -imidazol-4-yl; 1 H -imidazol-5-yl; 1H-pyrazole-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1 H-pyrazol-5-yl, 1 H-1, 2,3-triazol-1-yl, 1 H-1, 2,3-triazol-4-yl, 1 H-1, 2,3-triazole 5-yl, 2H-1, 2,3-triazol-2-yl, 2H-1, 2,3-triazol-4-yl, 1H-1, 2,4-triazol-1-y
  • heteroaryl groups according to the invention may furthermore be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics.
  • quinolines for example 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-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl
  • quinoxaline for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • quinoxaline e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-
  • quinazoline cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine;
  • heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indole-4 yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4 -yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl , 1-benzothiophene-5-yl, 1-benzothiophene
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
  • alky Denotes a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally mono- or polysubstituted, preferably unsubstituted, Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino- or nitro groups, particular preference is given to methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine.
  • Haloalkyl means the same or different
  • Polyhaloalkyl such. B. CH2CHFCI, CF2CCIFH, CF 2 CBrFH, CH2CF3;
  • perhaloalkyl also encompasses the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated
  • Hydrocarbon which is mono- or polysubstituted by fluorine, wherein the corresponding fluorine atoms as substituents on one or more
  • Hydrocarbon chain can be located, such as. B. CHFCH3, CH2CH2F, CH2CH2CF3, CHF 2, CH 2 F, CHFCF2CF3
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, all other optionally present
  • Halogen atoms are selected from the group fluorine, chlorine or bromine, iodine.
  • the corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes the
  • Haloalkoxy is eg OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl;
  • (C 1 -C 4) -alkyl given here by way of example means a A shorthand notation for straight-chain or branched alkyl having one to 4 carbon atoms corresponding to the range for C atoms, ie, the radicals comprises methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl , General alkyl radicals having a larger specified range of carbon atoms, eg. B. "(Ci-C-6) -alkyl", accordingly also include straight-chain or branched alkyl radicals having a larger number of carbon atoms, ie according to Example, the alkyl radicals having 5 and 6 carbon atoms.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl, even in assembled radicals, are the lower
  • Carbon skeletons e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, preferred.
  • Alkyl radicals also in the assembled radicals such as alkoxy, haloalkyl, etc., mean e.g.
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the Aikylresten, wherein at least one double bond or triple bond is included. Preference is given to radicals having a double bond or triple bond.
  • alkenyl also includes in particular straight-chain or branched open-chain carbon hydrogen radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds alkenyl is, for example, vinyl, which may optionally be substituted by further alkyl radicals, for example propylene-1-ene-1, such as, for example, allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.
  • alkynyl in particular also includes straight-chain or branched open-chain hydrocarbon radicals having more than one triple bond or else having one or more triple bonds and one or more double bonds such as 1,3-butatrienyl and 3-penten-1-yn-1-yl, respectively.
  • C 2 -C 6) -alkynyl is, for example, ethynyl, propargyl, 1-ethyl-prop-2-yn-1-yl, 2-butynyl,
  • 2-pentynyl or 2-hexynyl preferably propargyl, but-2-yn-1-yl, but-3-yn-1-yl or 1-ethyl-but-3-yn-1-yl.
  • cycloalkyl means a carbocyclic saturated ring system preferably having 3-8 ring C atoms, e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.
  • substituents also have one
  • an alkylidene group such as methylidene, are included.
  • optionally substituted cycloalkyl also become
  • polycyclic aliphatic systems such as, for example, bicyclo [.1] o-butan-1-yl, bicyclo [1 .1] -butan-2-yl, bicyclo [2.1.0] pentan-1-yl, bicyclo [2.1. 0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.2.1] hept-2-yl (norbornyl), bicyclo [2.2.2] octan-2-yl, adamantane-1 -yl and adamantan-2-yl.
  • (C3-C7) cycloalkyl means a shorthand notation for cycloalkyl having from three to seven carbon atoms corresponding to the range of C atoms.
  • substituted cycloalkyl are also spirocyclic aliphatic
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-
  • Alkylidene group such as methylidene, are included. In case of if necessary
  • alkylidene for example also in the form of (C 1 -C 10) -alkylidene, means the radical of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond naturally only positions on the body in question, where two H atoms can be replaced by the double bond; Remains are z.
  • Cycloalkylidene means a carbocyclic radical which is bonded via a double bond.
  • stannyl stands for a further substituted radical containing a tin atom
  • “Germanyl” is analogous to a further substituted radical which is a
  • Zeroconyl represents a further substituted radical containing a zirconium atom.
  • Hafnyl represents a further substituted radical containing a hafnium atom.
  • Boryl represents a further substituted radical containing a hafnium atom.
  • Boryl is further substituted and optionally cyclic groups, each containing a boron atom.
  • Plumbanyl represents a further substituted radical containing a lead atom.
  • Haldrargyl represents a further substituted radical containing a mercury atom.
  • Alignyl represents a further substituted radical containing an aluminum atom.
  • Magnnesyl represents a further substituted radical containing a magnesium atom.
  • Zincyl represents a further substituted radical containing a zinc atom.
  • the compounds of the general formula (I) can exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur.
  • Stereoisomers can be obtained from the resulting mixtures in the preparation by conventional separation methods. The chromatographic separation can be used both on an analytical scale for
  • stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
  • the invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof Synthesis:
  • Substituted 2-amidobenzimidazoles can be prepared by known methods (compare J. Med. Chem. 2000, 43, 4084, Bioorg. Med. Chem. 2008, 16, 6965, Bioorg. Med. Chem. 2008, 16, 3955; Org Proc. Res. Develop., 2007, 11, 693; J. Med. Chem. 2009, 52, 514; J. Heterocyclic Chem. 2001, 38, 979; WO2000026192;
  • Synthetic routes are based on commercially available or easily prepared 2-amino-3-nitrobenzoic acids or 2,3-diaminobenzonitriles.
  • the optionally additionally substituted 2-amino-3-nitrobenzoic acid in question can be converted with the aid of thionyl chloride and ammonia into the corresponding 2-amino-3-nitrobenzamide, either with hydrogen in the presence of palladium on carbon in a suitable solvent or with tin ( ll) chloride is reduced to an optionally further substituted 2,3-diaminobenzamide.
  • the thus obtained 2,3-diaminobenzamide can in the following step on various
  • Reaction variants eg., condensation with a carboxylic acid, with an aldehyde or an amidoxime can be converted into the desired benzimidazole derivative.
  • the corresponding benzimidazole can also be constructed by condensation of a 2,3-diaminobenzoic acid with a carboxylic acid or by N-acylation of a 2-amino-3-nitrobenzoic acid ester and subsequent reduction with hydrogen in the presence of palladium on carbon and the carboxyl function in the final step in the desired amide be transferred.
  • a further reaction route for the synthesis of the compounds according to the invention is the condensation of an optionally substituted 2,3-diaminobenzonitrile with a corresponding carboxylic acid and the subsequent reaction with a hydroxide base (eg.
  • Benzimidazole N-atom succeeds by deprotonation with a suitable base, for.
  • a suitable base for example, sodium hydride in an aprotic solvent, and subsequent reaction with a suitable electrophile, for example an acyl chloride, an alkyl halide or a chloroformate.
  • the amide group of the fluoroalkyl-substituted 2-amidobenzimidazoles prepared according to the invention can also be converted into the corresponding thioamide with the aid of 2,4-bis- (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane-2,4-disulfide or in a two-step synthesis by reaction with tert-butyl hypochlorite and AIBN in an aprotic solvent (e.g. B.
  • aprotic solvent e.g. B.
  • Substituted 2-amidobenzoxazoles can likewise be prepared by known processes (compare, Bioorg.Med.Chem., 2006, 14, 6106, WO2010083220;
  • optionally further substituted 2-amino-3-hydroxybenzoeklathylester is thereby converted with a suitable anhydride in THF or by condensation with a suitable carboxylic acid in the corresponding optionally substituted benzoxazole.
  • the ethyl ester is cleaved with the aid of a suitable hydroxide base (for example LiOH, KOH or NaOH) to give the optionally further substituted benzoxazolylcarboxylic acid, which may then be further introduced into the product according to the invention by using thionyl chloride and subsequent reaction of the acid chloride with ammonia substituted 2-amidobenzoxazole is transferred.
  • a suitable hydroxide base for example LiOH, KOH or NaOH
  • Substituted 2-amidobenzothiazoles can likewise be prepared analogously to the synthesis routes described above by processes known from the literature (compare Bioorg.Med.Chem. 2006, 14, 6106, WO2010083199).
  • further substituted 2-nitro-3-chlorobenzoic acids are first converted into the corresponding 2-amino-3-hydrothiobenzoic acids with the aid of sodium sulfide hydrate in a suitable polar protic solvent (eg methanol or water) (Scheme 4).
  • the relevant optionally further substituted 2-amino-3-hydrothiobenzoic acid is in this case with a suitable anhydride in THF or by direct condensation with a suitable carboxylic acid in the corresponding optionally further substituted benzothiazolylcarboxylic acid, which is subsequently purified by use of thionyl chloride or another suitable
  • Chlorination reagent eg., Oxalylchlorid
  • subsequent reaction of the acid chloride with ammonia to the optionally further substituted 2-amidobenzothiazole according to the invention is reacted.
  • the radicals R 1 , R 3 and Q mentioned in the following scheme 4 likewise have the meanings defined above.
  • Pentafluoropropionic anhydride (471 mg, 1.52 mmol) in abs. THF (2 ml) was added and the reaction mixture was kept at -78 ° C for 30 minutes and then for 1 hour
  • Compounds A5-1 to A5-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is chlorine, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A5-1 to A5-1000).
  • Residue definitions (Nos 1 to 1000, corresponding to compounds A10-1 to A10-1000).
  • A1 1 Compounds A1 1 -1 to A1 1 -1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is ethynyl, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 for the respective individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A1 1 -1 to A1 1 -1000).
  • Residue definitions (Nos 1 to 1000, corresponding to compounds A14-1 to A14-1000).
  • A15. Compounds A15-1 to A15-1000 of the general formula (I) wherein R 1 and R 2 are hydrogen, R 3 is fluorine, X is NR 4 and Q, W, Z ⁇ Z 2 and R 4 for the Respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A15-1 to A15-1000).
  • A16 Compounds A15-1 to A15-1000 of the general formula (I) wherein R 1 and R 2 are hydrogen, R 3 is fluorine, X is NR 4 and Q, W, Z ⁇ Z 2 and R 4 for the Respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A15-1 to A15-1000).
  • Compounds A17-1 to A17-1000 of the general formula (I) wherein R 1 and R 2 are hydrogen, R 3 is bromine, X is NR 4 and Q, W, Z ⁇ Z 2 and R 4 for the corresponding individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A17-1 to A17-1000).
  • Residue definitions (Nos 1 to 1000, corresponding to compounds A18-1 to A18-1000).
  • Residue definitions (nos 1 to 1000, corresponding to compounds A30-1 to A30-1000).
  • Residue definitions (Nos 1 to 1000, corresponding to compounds A32-1 to A32-1000).
  • A33 Compounds A33-1 to A33-1000 of the general formula (I) wherein R 1 and R 3 are hydrogen, R 2 is ethenyl, X is NR 4 and Q, W, Z ⁇ Z 2 and R 4 for the corresponding individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A33-1 to A33-1000).
  • A34 Compounds A34-1 to A 34-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is cyclobutyl, X is NR 4 and Q, W, Z 1 , Z 2 and
  • R 4 for the respective individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A34-1 to A34-1000).
  • Residue definitions (nos 1 to 1000, corresponding to compounds A36-1 to A36-1000).
  • the present invention thus provides the use of at least one compound selected from the group consisting of substituted
  • abiotic stress factors preferably drought stress
  • a further subject of the present invention is a spray solution for the treatment of plants, comprising an amount of at least one effective for increasing the resistance of plants to abiotic stress factors
  • heat, drought, cold and drought stress stress caused by drought and / or water deficiency
  • osmotic stress waterlogging
  • increased soil salt content increased exposure to minerals, ozone conditions
  • High light conditions limited availability of nitrogen nutrients, limited availability of phosphorus nutrients.
  • Substituted 2-Amidobenzimidazole, 2-Amidobenzoxazole and 2-amidobenzothiazoles of the general formula (!), are applied by a spray application to appropriate plants or plant parts to be treated.
  • the use according to the invention of the compounds of the general formula (I) or salts thereof is preferably carried out with a dosage of between 0.00005 and 3 kg / ha, more preferably between 0.0001 and 2 kg / ha, particularly preferably between 0.0005 and 1 kg / ha, more preferably between 0.001 and 0.25 kg / ha.
  • the admixing of abscisic acid is preferably carried out in one dosage between 0.0001 and 3 kg / ha, more preferably between 0.001 and 2 kg / ha, particularly preferably between 0.005 and 1 kg / ha, in particular preferably between 0.006 and 0.25 kg / ha.
  • resistance or resistance to abiotic stress is understood to mean various advantages for plants. Such advantageous properties are manifested, for example, in the following improved plant characteristics: improved root growth in terms of surface area and depth, increased tailing or stocking, stronger and more productive shoots and tillers,
  • Sprout base diameter increased leaf area, higher yields of nutrients and ingredients, such as carbohydrates, fats, oils, proteins, vitamins, minerals, essential oils, dyes, fibers, better fiber quality, earlier flowering, increased number of flowers, reduced content of toxic products such as mycotoxins , reduced content of residues or unfavorable ingredients of any kind or better digestibility, improved storage stability of the crop, improved tolerance to unfavorable temperatures, improved tolerance to drought and Dryness, as well as lack of oxygen due to excess water, improved
  • nutrients and ingredients such as carbohydrates, fats, oils, proteins, vitamins, minerals, essential oils, dyes, fibers, better fiber quality, earlier flowering, increased number of flowers, reduced content of toxic products such as mycotoxins , reduced content of residues or unfavorable ingredients of any kind or better digestibility, improved storage stability of the crop, improved tolerance to unfavorable temperatures, improved tolerance to drought and Dryness, as well as lack of oxygen due to excess water, improved
  • Photosynthesis beneficial plant properties, such as
  • 2-amidobenzimidazoles according to the invention, 2-amidobenzoxazoles and 2-amidobenzothiazoles of the general formula (I) inter alia with insecticides, attractants, acaricides, fungicides, nematicides, herbicides,
  • Amidobenzothiazoles of general formula (I) with genetically modified varieties with respect to increased abiotic stress tolerance is also possible.
  • Non-limiting resistance to abiotic stress ⁇ at least one in general 3%, in particular greater than 5%
  • At least one root development generally improved by 3%, in particular greater than 5%, particularly preferably greater than 10%,
  • At least one shoot size increasing by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
  • At least one leaf area increased by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
  • a further subject of the present invention is a spray solution for the treatment of plants, comprising an amount of at least one effective for increasing the resistance of plants to abiotic stress factors
  • the spray solution may comprise other conventional ingredients, such as solvents, formulation auxiliaries, especially water.
  • Other ingredients may include agrochemical agents, which are further described below.
  • Another object of the present invention is the use of
  • potassium salts preferably chlorides, sulfates, nitrates
  • phosphoric acid salts and / or salts of phosphorous acid preferably potassium salts and ammonium salts.
  • NPK fertilizers ie fertilizers containing nitrogen, phosphorus and potassium, calcium ammonium nitrate, ie fertilizers which still contain calcium, ammonium sulphate nitrate (general formula (NH 4 ) 2 SO 4 NH 4 NO 3), ammonium phosphate and ammonium sulphate.
  • ammonium sulphate nitrate generally formula (NH 4 ) 2 SO 4 NH 4 NO 3
  • ammonium phosphate and ammonium sulphate generally known to those skilled in the art, see also, for example, Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A 10, pages 323 to 431, Verlagsgesellschaft, Weinheim, 1987.
  • the fertilizers may also contain salts of micronutrients (preferably calcium,
  • Fertilizers used according to the invention may also contain other salts such as monoammonium phosphate (MAP), diammonium phosphate (DAP), potassium sulfate,
  • fertilizers Containing potassium chloride, magnesium sulfate. Suitable amounts for the secondary nutrients or trace elements are amounts of 0.5 to 5 wt .-%, based on the total fertilizer.
  • Further possible ingredients are crop protection agents, insecticides or fungicides, growth regulators or mixtures thereof. Further explanations follow below.
  • the fertilizers can be used, for example, in the form of powders, granules, prills or compactates. However, the fertilizers can also be used in liquid form dissolved in an aqueous medium. In this case, dilute aqueous ammonia can be used as nitrogen fertilizer. Further possible ingredients for fertilizers are, for example, in Ullmann's
  • the general composition of the fertilizers which in the context of the present invention may be single-nutrient and / or complex nutrient fertilizers,
  • nitrogen, potassium or phosphorus may vary within a wide range.
  • a content of 1 to 30 wt .-% of nitrogen preferably 5 to 20 wt .-%), from 1 to 20 wt .-% potassium (preferably 3 to 15% by weight) and a content of 1 to 20% by weight of phosphorus (preferably 3 to 10% by weight) is advantageous.
  • the content of microelements is usually in the ppm range, preferably in the range of from 1 to 1000 ppm.
  • the fertilizer and one or more compounds of the general formula (I) can be administered at the same time.
  • the fertilizer and one or more compounds of the general formula (I) can be administered at the same time.
  • it is also possible first the fertilizer and then one or more compounds of the general formula (I) can be administered at the same time.
  • inventive compounds of formula (I) and the fertilizer in a time frame of less than 1 hour, preferably less than 30 minutes, more preferably less than 15 minutes.
  • the forest stock includes trees for the production of wood, pulp, paper and products made from parts of the trees.
  • crops as used herein refers to
  • Among the useful plants include z.
  • the following plant species Triticale, Durum
  • Durum wheat turf, vines, cereals, such as wheat, barley, rye, oats, rice, corn and millet
  • Beets for example sugar beets and fodder beets
  • Fruits such as pome fruit, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries and berries, eg. Strawberries, raspberries, blackberries
  • Legumes such as beans, lentils, peas and soybeans
  • Oil crops such as oilseed rape, mustard, poppy, olives, sunflowers, coconut,
  • Castor oil plants cocoa beans and peanuts; Cucurbits, for example squash, cucumbers and melons; Fiber plants, for example cotton, flax, hemp and jute; Citrus fruits, such as oranges, lemons, grapefruit and mandarins; Vegetables such as spinach, (head) salad, asparagus, cabbages, carrots, onions, tomatoes, potatoes and peppers; Laurel family, such as avocado, cinnamomum, camphor, or plants such as tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, vines, hops, bananas,
  • Natural rubber plants and ornamental plants such as flowers, shrubs, deciduous trees and conifers such as conifers. This list is not a limitation.
  • Particularly suitable target crops for the application of the method according to the invention are the following plants: oats, rye, triticale, durum, cotton, aubergine, turf, pome fruit, stone fruit, berry fruit, corn, wheat, barley, cucumber, tobacco, vines, rice, cereals , Pear, pepper, beans, soybeans, rape, tomato, paprika, melons, cabbage, potato and apple.
  • Examples of trees which can be improved according to the process of the invention are: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., PSatanus sp., Tilia sp., Acer sp., Tsuga sp., Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp ., Populus sp ..
  • trees which can be improved according to the method of the invention, may be mentioned: From the tree species Aesculus: A. hippocastanum, A. pariflora, A. carnea; from the tree species Platanus: P. aceriflora, P. occidentalis, P. racemosa; from the tree species Picea: P. abies; from the tree Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P.
  • albicaulis P. resinosa, P. palustris, P. taeda, P. flexilis, P. jeffregi, P. baksiana, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis, E.
  • the present invention may also be practiced on any turfgrasses, including "cool season turfgrasses” and “warm season turfgrasses.”
  • cold season turf species are blue grasses (Poa spp.), Such as “Kentucky bluegrass” (Poa pratensis L), “rough bluegrass” (Poa trivialis L), “Canada bluegrass” (Poa compressa L), “annual bluegrass” (Poa annua L), “upland bluegrass” (Poa glaucantha Gaudin), “Wood bluegrass” (Poa nemoralis L.) and “bulbous bluegrass” (Poa bulbosa L); ostrich grasses ("Bentgrass”, Agrostis spp.), Such as “creeping bentgrass” (Agrostis palustris Huds.), “Colonial bentgrass” (Agrostis Tenuis Sibth.), “velvet bentgrass” (Agrostis canina L),
  • Lolium ryegrasses, Lolium spp.
  • Examples of other "cool season turfgrasses” are “beachgrass” (Ammophila breviligulata Fern.), “smooth bromegrass” (Bromus inermis leyss.), reeds (“cattails”) such as “Timothy” (Phleum pratense L.
  • orchardgrass (Dactylis glomerata L.), "weeping alkaligrass” (Puccinellia distans (L.) Pari.) and “crested dog's-tail” (Cynosurus cristatus L.).
  • Examples of “warm season turfgrasses” are “Bermudagrass” (Cynodon spp., LC Rieh), “zoysiagrass” (Zoysia spp. Willd.), “St. Augustine grass” (Stenotaphrum secundatum Walt Kuntze), “centipedegrass” (Eremochloa ophiuroides Munrohack.), “Carpetgrass” (Axonopus affinis chase), “Bahia grass” (Paspalum notatum flügge), “Kikuyugrass” (Pennisetum clandestinum detergent, ex Chiov.), “Buffalo grass” (Buchloe daetyloids (Nutt.) Engelm.) , “Blue gramma” (Bouteloua gracilis (HBK) lag.
  • the compounds of general formula (I) according to the invention plants of each commercial or in use treated plant varieties.
  • Plant varieties are understood to be plants with new traits which have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques.
  • Crop plants can therefore be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties protectable or non-protectable plant varieties.
  • the treatment method according to the invention can thus also for the treatment of genetically modified organisms (GMOs), z.
  • GMOs genetically modified organisms
  • Genetically modified plants or transgenic plants
  • heterologous gene essentially means a gene that is provided or assembled outside the plant and that when introduced into the plant
  • Cell nucleus genome, the chloroplast genome or the hypochondrial genome of the transformed plant by conferring new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by having another gene present in the plant or other genes present in the plant; downregulated or switched off (for example by means of antisense technology, co-suppression technology or RNAi technology [RNA Interference]).
  • a heterologous gene present in the genome is also referred to as a transgene.
  • a transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.
  • Plants and plant varieties which are preferably treated with the compounds of the general formula (I) according to the invention include all plants which have genetic material which gives these plants particularly advantageous, useful features (regardless of whether this is achieved by breeding and / or biotechnology has been).
  • Plants and plant varieties which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are resistant to one or more abiotic stress factors. To the abiotic stress factors,
  • Stress conditions can include, for example, heat, drought, cold and dry stress, osmotic stress, waterlogging, increased soil salt content, increased exposure to minerals, ozone conditions, high light conditions, limited availability of
  • Nitrogen nutrients limited availability of phosphorus nutrients or avoiding shadows.
  • Plants and plant varieties which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are characterized by increased yield properties. An increased yield can in these plants z. B. on improved plant physiology, improved
  • Plant growth and improved plant development such as
  • the yield may be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for the production of hybrid seed,
  • Root growth seed size, fruit size, pod size, pods or
  • Plants which can also be treated with the compounds of the general formula (I) according to the invention are hybrid plants which have already been used
  • Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner).
  • the hybrid seed is typically harvested from the male sterile plants and sold to propagators.
  • Pollen sterile plants can sometimes (for example in the case of corn) by Entfahnen (ie mechanical removal of male genitalia or male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome.
  • the desired product as one wants to harvest from the hybrid plants, is the seeds, it is usually beneficial to ensure that the pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility , completely restored. This can be accomplished by ensuring that the male crossbred partners possess appropriate fertility restorer genes capable of controlling pollen fertility in humans
  • Pollen sterility may be localized in the cytoplasm.
  • CMS cytoplasmic male sterility
  • Brassica species WO 92/005251, WO 95/009910, WO 98/27806, WO 05/002324, WO 06/021972 and US 6,229,072
  • genetic determinants of pollen sterility can also be found in the
  • Pollen sterile plants can also be obtained using plant biotechnology methods such as genetic engineering.
  • a particularly convenient means of producing male-sterile plants is described in WO 89/10396, wherein, for example, a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens.
  • the fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells (eg WO 91/002069).
  • Plants or plant varieties which are obtained by plant biotechnology methods, such as genetic engineering), which also with the inventive
  • herbicide-tolerant plants d. H. Plants tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation conferring such herbicide tolerance.
  • Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H.
  • glyphosate-tolerant plants can Transformation of the plant with a gene encoding the enzyme 5-enolpyruvylshikimat 3-phosphate synthase (EPSPS) can be obtained.
  • EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., Science (1983), 221, 370-371), the CP4 gene of the bacterium
  • Glyphosate-tolerant plants can also be obtained by expressing a gene coding for a glyphosate oxidoreductase enzyme as described in US 5,776,760 and US 5,463,175. Glyphosate-tolerant plants may also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described in, e.g. WO 02/036782, WO 03/092360, WO 05/012515 and WO 07/024782. Glyphosate-tolerant plants can also be obtained by culturing plants containing the naturally occurring mutations of the above-mentioned genes, as described, for example, in WO 01/024615 or WO
  • herbicide-resistant plants are, for example, plants which have been tolerated to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate.
  • Such plants can be obtained by expressing an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition.
  • an effective detoxifying enzyme is, for example, an enzyme suitable for
  • Phosphinotricin acetyltransferase encoded such as the bar or pat protein from Streptomyces species. Plants expressing an exogenous phosphinotricin acetyltransferase are described, for example, in US 5,561,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 and US 7,112,665.
  • hydroxyphenylpyruvate dioxygenase HPPD
  • HPPD hydroxyphenylpyruvate dioxygenase
  • the hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate.
  • Plants tolerant to HPPD inhibitors may be treated with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutant HPPD enzyme according to WO 96/038567, WO
  • Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants and genes are described in WO 99/034008 and WO 2002/36787.
  • the tolerance of plants to HPPD inhibitors can also be improved by transforming plants, in addition to a gene which codes for an HPPD-tolerant enzyme, with a gene which codes for a prephenate dehydrogenase enzyme, as described in WO 2004 / 024928 is described.
  • ALS acetolactate synthase
  • known ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines,
  • Acetohydroxy acid synthase known
  • Sulfonylurea and imidazolinone tolerant plants are also useful in e.g. WHERE
  • Imidazolinones, sulfonylureas and / or sulfamoylcarbonyltriazolinones can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutagenesis, as for example for the soybean in US 5,084,082, for rice in WO 97/41218, for the sugar beet in US 5,773,702 and WO 99/057965, for salad in US 5,198,599 or for the sunflower in WO 2001/065922.
  • Plants or plant varieties obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
  • insect-resistant transgenic plants i. Plants that have been made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance.
  • an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof such as the insecticidal crystal proteins collected by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, by Crickmore et al. (2005) in the Bacillus thuringiensis toxin nomenclature (online at:
  • insecticidal parts thereof e.g. Proteins of Cry protein classes CrylAb, CrylAc, Cryl F, Cry2Ab, Cry3Ae or Cry3Bb or insecticidal parts thereof; or 2) a crystal protein from Bacillus thuringiensis or a part thereof which is present in
  • a second, different crystal protein than Bacillus thuringiensis or a part thereof insecticide such as the binary toxin consisting of the crystal proteins Cy34 and Cy35 (Moellenbeck et al., Nat. Biotechnol. (2001), 19, 668-72; Schnepf et al., Applied Environment Microb. (2006) 71, 1765-1774); or 3) an insecticidal hybrid protein comprising parts of two different insecticides of Bacillus thuringiensis crystal proteins, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g.
  • the protein Cry1A.105 produced by the corn event MON98034 WO
  • amino acids have been replaced by another amino acid to achieve higher insecticidal activity against a target insect species and / or to broaden the spectrum of the corresponding target insect species and / or due to changes in the coding DNA during cloning or Transformation were induced, such as the protein Cry3Bb1 in maize events MON863 or MON88017 or the protein Cry3A in the maize event MIR 604; or
  • VIP3Aa Proteins of protein class VIP3Aa:
  • a secreted protein from Bacillus thuringiensis or Bacillus cereus which acts in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus insecticide, such as the binary toxin consisting of the proteins VIP1A and VIP2A (WO 94/21795); or
  • an insecticidal hybrid protein comprising parts of various secreted proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins of 1) or a hybrid of the proteins of 2) above; or
  • insect-resistant transgenic plants in the present connection also any plant comprising a combination of genes coding for the proteins of any of the above classes 1 to 8.
  • an insect resistant plant contains more than one transgene encoding a protein of any one of the above 1 to 8 in order to extend the spectrum of the corresponding target insect species or to develop a protein
  • Plants or plant varieties obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
  • Compounds of general formula (I) are tolerant to abiotic stressors. Such plants can be caused by genetic
  • Transformation or by selection of plants containing a mutation conferring such stress resistance include the following: a. Plants which contain a transgene which have the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or
  • Nicotinate phosphoribosyltransferase nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase, as described e.g. As described in EP 04077624.7 or WO 2006/133827 or PCT / EP07 / 002433.
  • Plants or plant varieties obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
  • Compounds of general formula (I) may have an altered amount, quality and / or shelf life of the harvested product and / or altered properties of certain components of the harvested product, such as:
  • Viscosity behavior the gel strength, the starch grain size and / or
  • Wildtype plants are modified without genetic modification. Examples are plants which produce polyfructose, in particular of the inulin and levan type, as described in EP 0663956, WO 96/001904, Wo 96/021023, WO 98/039460 and WO 99/024593, plants which are alpha-1 To produce 4-glucans, as in WO
  • Plants or plant varieties obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
  • plants of general formula (I) can be treated are plants such as cotton plants with altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; These include: a) plants, such as cotton plants, which have an altered form of
  • cellulose synthase genes Contain cellulose synthase genes, as described in WO 98/000549, b) plants, such as cotton plants, which contain an altered form of rsw2 or rsw3-homologous nucleic acids, as described in WO 2004/05329; c) plants such as cotton plants with an increased expression of the
  • Sucrose phosphate synthase as described in WO 2001/017333; d) plants such as cotton plants with an increased expression of
  • Sucrose synthase as described in WO 02/45485; e) plants such as cotton plants in which the timing of the passage control of the Plasmodesmen is changed at the base of the fiber cell, z. B. by
  • Plants or plant varieties obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
  • Compounds of general formula (I) can be treated are plants such as rapeseed or related Brassica plants with altered properties of
  • Oil composition Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; These include: a) plants such as rape plants that produce high oleic oil, as described, for example, in US 5,969,169, US 5,840,946 or US 6,323,392 or US 6,063,947; b) plants such as oilseed rape plants which produce low linolenic acid oil, as described in US 6,270,828, US 6,169,190 or US 5,965,755. c) plants such as rape plants, which produce oil with a low saturated fatty acid content, as z. As described in US 5,434,283. Particularly useful transgenic plants with the inventive
  • Compounds of general formula (I) may be treated as plants containing transformation events, or a combination of transformation events, for example as listed in the files of various national or regional authorities.
  • Exemplary plants having one or more genes encoding one or more toxins are the transgenic plants available under the following tradenames: YIELD GARD® (for example, corn, cotton , Soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example maize), StarLink® (for example corn), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn),
  • Herbicide-tolerant crops to be mentioned include, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready®
  • Herbicide-resistant plants plants traditionally grown for herbicide tolerance
  • Clearfield® for example corn
  • the compounds of the formula (I) to be used according to the invention can be converted into customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, Active substance - impregnated natural substances, active substance-impregnated synthetic substances, fertilizers and microencapsulation in polymeric substances.
  • customary formulations such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, Active substance - impregnated natural substances, active substance-impregnated synthetic substances, fertilizers and microencapsulation in polymeric substances.
  • customary formulations such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powder
  • the present invention therefore further relates to a spray formulation for increasing the resistance of plants to abiotic stress.
  • a spray formulation is described in more detail:
  • the formulations for spray application are prepared in a known manner, e.g. by mixing the compounds of the formula (I) to be used according to the invention with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders ie liquid solvents and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
  • Other conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives,
  • Gibberellins and also water may also be used if necessary.
  • the preparation of the formulations is carried out either in suitable systems or before or during use.
  • Excipients which can be used are those which are suitable for imparting special properties to the composition itself or to preparations derived therefrom (for example spray mixtures), such as certain technical properties and / or special biological properties.
  • spray mixtures for example spray mixtures
  • typical aids are:
  • Hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or esterified
  • ketones such as acetone, cyclohexanone
  • esters including fats and oils
  • Poly ethers simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide).
  • organic solvents can also be used as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Suitable wetting agents which may be present in the formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
  • Preferably usable are alkylnaphthalene sulfonates such as diisopropyl or diisobutylnaphthalene sulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds.
  • Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • Defoamers which can be used in the formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds Be contained substances. Preference is given to using silicone defoamers and magnesium stearate.
  • Formulations all substances that can be used for such purposes in agrochemical agents be present. Examples include dichlorophen and benzyl alcohol hemiformal.
  • Suitable secondary thickeners which may be present in the formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions.
  • suitable are cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
  • Further additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also micronutrients), such as salts of iron, manganese, boron , Copper, cobalt, molybdenum and zinc, stabilizers such as low-temperature stabilizers, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents.
  • nutrients also micronutrients
  • stabilizers such as low-temperature stabilizers, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents.
  • the formulations generally contain between 0.01 and 98% by weight, preferably between 0.5 and 90%, of the compound of general formula (I).
  • the compounds of general formula (I) according to the invention can be prepared in commercial formulations and in the formulations prepared from these formulations in admixture with other active substances such as insecticides,
  • Attractants sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or
  • the described positive effect of the compounds of the formula (I) on the plant's own defenses can be assisted by additional treatment with insecticidal, fungicidal or bactericidal active substances.
  • Preferred times for the application of the compounds of the general formula (I) to be used according to the invention or their salts for increasing the resistance to abiotic stress are soil, parent and / or
  • the active compounds of the general formula (I) or salts thereof to be used according to the invention can generally also be used in their commercial form
  • F1 inhibitors of nucleic acid synthesis e.g. Benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon, dimethirimo S, ethirimol, furaiaxyl, hymexazole, metalaxyl, metalaxyl-M, ofurace, oxadixyl, oxolinic acid;
  • F2 inhibitors of mitosis and cell division, e.g. Benomyl, carbendazim, diethofencarb, fuberidazole, fluopicolide, pencycuron, thiabendazole, thiophanate-methyl, zoxamide and chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1, 2 , 4] triazolo [1,5-ajpyrimidine;
  • Benomyl carbendazim
  • diethofencarb fuberidazole
  • fluopicolide fluopicolide
  • pencycuron thiabendazole
  • thiophanate-methyl zoxamide
  • Cyazofamide dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoximethyl, metominostrobin, orysastrobin, pyraclostrobin, pyribencarb,
  • F6 inhibitors of ATP production e.g. Fentin acetate, fentin chloride, fentin hydroxide, silthiofam
  • inhibitors of amino acid and protein biosynthesis e.g. Andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim,
  • F10) inhibitors of ergosterol biosynthesis eg. Fenhexamid, azaconazole, bitertanol, bromuconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, penconazole, Propiconazole, Prothioconazole, Simeconazole, Spiroxamine, Tebuconazole, Triadimefon, Triadimenol, Triticonazole, Uniconazole, Voriconazole, Imazalil,
  • F1 1) inhibitors of cell wall synthesis, e.g. Benthiavalicarb, Bialaphos,
  • F12 inhibitors of melanin biosynthesis, e.g. Capropamide, diclocymet, fenoxanil, phtalid, pyroquilone, tricyclazole F13) resistance induction, e.g. Acibenzolar-S-methyl, probenazole, tiadinil
  • Unknown mechanism e.g. Amibromdole, benthiazole, bethoxazine,
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g.
  • Organophosphates e.g. Acephates, azamethiphos, azinphos (-methyl, -ethyl),
  • Dicrotophos dimethoates, dimethylvinphos, disulphoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthione, fosthiazate, heptenophos, isofenphos, isopropyl O- (methoxyaminothio-phosphoryl) salicylate, isoxathione, malathion, mec-carbam, methamidophos, ethidathione, Mevinphos, Monocrotophos, Naled,
  • Phosalone Phosmet, Phosphamidone, Phoxim, Pirimiphos (-methyl), Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep,
  • Tebupirimfos Temephos, Terbufos, Tetrachlorvinphos, Thiometone, Triazophos, Triclorfon and Vamidothion.
  • GABA-controlled chloride channel antagonists such as organo-chiorines, e.g. Chlordane and endosulfan (alpha); or fiproles (phenylpyrazoles), e.g. Ethiprole, Fipronil, Pyrafluprole and Pyriprole.
  • organo-chiorines e.g. Chlordane and endosulfan (alpha)
  • fiproles phenylpyrazoles
  • Ethiprole e.g. Ethiprole, Fipronil, Pyrafluprole and Pyriprole.
  • Sodium channel modulators / voltage dependent sodium channel blockers such as pyrethroids, e.g. Acrinathrin, allethrin (d-cis-trans, d-trans), bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin (beta-), cyhalothrin (gamma, lambda), cypermethrin (alpha-, beta , theta, zeta), cychenothrin [(1R) -fra / 7s isomers], deltamethrin, dimefluthrin, empenthrin [(EZ) (1R) isomers], esfenvalerates, etofenprox, fenpropathrin, fenvalerates , Flucythrinates, flumethrin, fluval
  • nicotinergic acetylcholine receptor agonists such as neonicotinoids, eg, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; or nicotine.
  • aceiylcholine receptor moduators agonists
  • spinosyns eg spinetoram
  • spinosad thiamethoxam
  • chloride channel activators such as avermectins / milbemycins, eg
  • Juvenile hormone analogs e.g. Hydroprene, kinoprene, methoprene; or
  • Active ingredients with unknown or non-specific mechanisms of action such as fumigants, e.g. Methyl bromide and other alkyl halides; or chloropicrin; sulfuryl fluoride; Borax; Tartar emetic.
  • Selective feeding inhibitors e.g. pymetrozine; or flonicamide.
  • mite growth inhibitors e.g. Clofentezine, diflovidazine, hexythiazox, etoxazole.
  • inhibitors of oxidative phosphorylation such as diafenthiuron; or organotin compounds, e.g. Azocyclotine, cyhexatin, fenbutatin oxide; or propargite; Tetrad ifon.
  • ATP disruptors such as diafenthiuron
  • organotin compounds e.g. Azocyclotine, cyhexatin, fenbutatin oxide; or propargite; Tetrad ifon.
  • Decoupling of oxidative phosphorylation by interruption of the H proton gradient such as chlorfenapyr and DNOC.
  • nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap (hydrochloride), thiocyclam, and thiosultap (-sodium).
  • inhibitors of chitin biosynthesis, type 0, such as benzoylureas, eg bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron,
  • inhibitors of chitin biosynthesis type 1, such as buprofezin.
  • Moisture-disrupting agents such as cyromazines.
  • ecdysone agonists / disruptors such as diacylhydrazines, e.g.
  • Chromafenozide Halofenozide, Methoxyfenozide and Tebufenozide.
  • Octopaminergic agonists such as amitraz.
  • I20 complex I l electron transport inhibitors such as, for example, hydramethylnone; acequinocyl; Fluacrypyrim.
  • Complex I electron transport inhibitors for example from the group of the METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad; or Rotenone (Derris).
  • METI acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad; or Rotenone (Derris).
  • voltage dependent sodium channel blockers e.g. indoxacarb; Metaflumizone.
  • inhibitors of acetyl-CoA carboxylase such as tetronic acid derivatives, e.g. Spirodiclofen and spiromesifen; or tetramic acid derivatives, e.g. Spirotetramat.
  • complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine, zinc phosphide; or cyanide.
  • phosphines e.g. Aluminum phosphide, calcium phosphide, phosphine, zinc phosphide; or cyanide.
  • Complex I l electron transport inhibitors such as cyenopyrafen.
  • ryanodine receptor effectors such as, for example, diamides, eg flubendiamide, chiorantraniipyrole (rynaxypyr), cyantraniliproie (cyazypyr) and 3-bromo-N- ⁇ 2-bromo-4-chloro-6 - [(1-cyclopropylethyl) carbamoyl] phenyl ⁇ -1 - (3-chloropyridin-2-yl) -1H-pyrazole-5- carboxamide (known from WO2005 / 077934) or methyl 2- [3,5-dibromo-2 - ( ⁇ [3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl ⁇ amino) benzoyl] -1, 2-dimethylhydrazinecarboxylate (known from WO2007 / 043677).
  • Other drugs with unknown mechanism of action such as
  • Triazole-5-amines (known from WO 2006/043635), [(3S, 4aR, 12R, 12aS, 12 ⁇ S) -3- [(cyclopropylcarbonyl) oxy] -6,12-dihydroxy-4,12b-dimethyl-11 -oxo-9- (pyridin-3-yl) -1,4,4,4a, 5,6,6a, 12,12a, 12 ⁇ -decahydro-2H, 1: 1 H-benzo [f] pyrano [4,3 -b] chromen-4-yl] methylcyclopropanecarboxylate (known from WO 2006/129714), 2-cyano-3- (difluoromethoxy) -N, N-dimethylbenzenesulfonamide (known from WO2006 / 056433), 2-cyano-3- (difluoromethoxy ) -N-methylbenzenesulfonamide (known from WO2006 / 100288), 2-cyano-3- (d
  • Safeners are preferably selected from the group consisting of:
  • riA is a natural number of 0 to 5, preferably 0 to 3;
  • RA 1 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, nitro or (C 1 -C 4 ) haloalkyl;
  • WA is an unsubstituted or substituted divalent heterocyclic radical selected from the group consisting of the monounsaturated or aromatic five-membered heterocycles having 1 to 3 hetero ring atoms from the group N and O, where at least one N atom and at most one O atom are present in the ring, preferably one Remainder of the group (W A 1 ) to (WA 4 ),
  • rriA is 0 or 1
  • RA 2 is ORA 3 , SRA 3 or NRA 3 RA 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is bonded via the N- Atom is connected to the carbonyl group in (S1) and is unsubstituted or substituted by radicals from the group (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy or optionally substituted phenyl, preferably a radical of the formula ORA 3 , NHRA 4 or N (CH 3) 2, in particular of the formula ORA 3 ;
  • RA 3 is hydrogen or an unsubstituted or substituted aliphatic
  • Carbon hydrogen radical preferably having a total of 1 to 18 carbon atoms
  • RA 4 is hydrogen, (Ci-Ce) alkyl, (Ci-Ce) alkoxy or substituted or
  • RA 5 is H, (C 1 -C 8 ) alkyl, (C 1 -C 8 ) haloalkyl, (C 1 -C 4 ) alkoxy (C 1 -C 8 ) alkyl, cyano or COORA 9 , in which R A 9 is hydrogen, (C 1 -C 8 ) alkyl, (Ci-C 8) haloalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-Ce) hydroxyalkyl, (C3-Ci2) -cycloalkyl or tri- (Ci-C 4 ) -alkyl-silyl; RA 6 , RA 7 , RA 8 are identical or different hydrogen, (C 1 -C 8 ) alkyl, (C 1 -C 8 ) haloalkyl,
  • Ci2 cycloalkyl or substituted or unsubstituted phenyl; preferably: a) compounds of the type of dichlorophenylpyrazoline-3-carboxylic acid (S1 a ), preferably compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid, 1- ( 2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoiin-3-carboxylic acid ethyl ester (S1 -1) ("mefenpyr-diethyl”), and related compounds, as described in WO-A -91 / 07874 are described;
  • S1 C 1,5-diphenylpyrazole-3-carboxylic acid
  • S1 C preferably compounds such as 1- (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylic acid ethyl ester (S1 -5), 1- (2 -Chlorphenyi) -5-phenylpyrazole-3-carboxylic acid methyl ester (S1 -6) and related compounds as described for example in EP-A-268554;
  • RB 1 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, nitro or (C 1 -C 4 ) haloalkyl;
  • ne is a natural number of 0 to 5, preferably 0 to 3;
  • RB 2 is OR B 3 , SRB 3 or NR B 3 RB 4 or a saturated one
  • RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 8 C atoms;
  • RB 4 is hydrogen, (Ci-Ce) alkyl, (Ci-Ce) alkoxy or substituted or
  • TB is a (Ci or C2) alkanediyl chain which is unsubstituted or substituted by one or two (Ci-C) alkyl radicals or by [(d-C3) alkoxy] carbonyl; preferably:
  • Rc 1 is (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl,
  • (C3-C) cycloalkyl preferably dichloromethyl
  • Rc 2, rc 3 are identical or different hydrogen, (Ci-C 4) alkyl, (C2-C4) alkenyl, (C 2 -C) alkynyl, (Ci-C 4) haloalkyl, (C 2 -C 4) haloalkenyl, (Ci-C 4) alkylcarbamoyl (Ci-C) alkyl, (C 2 -C 4) Alkenylcarbamoyl- (Ci-C) alkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, dioxolanyl (Ci-C) alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc 2 and Rc 3 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine,
  • Pre-emergence safeners are applied, such. B.
  • X D is CH or N
  • RD 1 is CO-NR D 5 RD 6 or NHCO-RD 7 ;
  • RD 2 is halogen, (Ci-C 4) haloalkyl, (Ci-C 4) haloalkoxy, nitro, (Ci-C 4) alkyl,
  • RD 3 is hydrogen, (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkenyl or (C 2 -C 4 ) alkynyl;
  • R D 4 is halogen, nitro, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy,
  • RD 5 is hydrogen, (Ci-C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (Cs-CeJCycloalkenyl, phenyl or 3-6 heterocyclyl-containing hetero-hetero atoms from the group consisting of nitrogen, oxygen and sulfur, where the last seven radicals are represented by VD substituents from the group consisting of halogen, (C 1 -C 6 -alkoxy, (C 1 -C 6 ) -haloalkoxy, (C 1 -C 2 ) -alkylsulfinyl, ( Ci-C 2 ) alkylsulfonyl, (C 3 -C 6 ) cycloalkyl, (Ci- C 4 ) alkoxycarbonyl, (Ci-C 4 ) alkylcarbonyl and phenyl and in
  • RD 7 is hydrogen, (Ci-C 4) alkylamino, di (Ci-C 4) alkylamino, (Ci-C 6) alkyl,
  • (C3-C6) cycloalkyl where the 2 last-mentioned radicals by VD substituents selected from the group consisting of halogen, (Ci-C 4 ) alkoxy, (d-C6) haloalkoxy and (Ci-C 4 ) alkylthio and in the case of cyclic radicals also (Ci -C 4) alkyl and (Ci-C4) haloalkyl groups;
  • n D 0, 1 or 2;
  • VD is 0, 1, 2 or 3; Of these, preference is given to compounds of the N-acylsulfonamide type, for example of the following formula (S4 a ), which are, for example, B. are known from WO-A-97/45016
  • RD 7 (Ci-C6) alkyl, (C3-C-6) cycloalkyl, wherein the latter two radicals by VD substituents selected from the group consisting of halogen, (Ci-C 4 ) alkoxy, (Ci-Ce) haloalkoxy and (d-C 4 ) alkylthio and in the case of cyclic radicals are also (Ci-C4) alkyl and (Ci-C 4 ) haloalkyl substituted;
  • RD 4 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3;
  • ITID 1 or 2

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Abstract

The invention relates to the use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles of general formula (I) or the salts thereof, the groups in general formula (I) corresponding to the definitions cited in the description, for increasing the stress tolerance of plants to abiotic stress, for strengthening plant growth and/or for increasing the plant yield. The invention also relates to specific methods for producing said compounds.

Description

Verwendung substituierter 2-Amidobenzimidazole, 2-Amidobenzoxazole und 2- Amidobenzothiazole oder deren Salze als Wirkstoffe gegen abiotischen Pflanzenstress  Use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles or their salts as active ingredients against abiotic plant stress
Beschreibung description
Die Erfindung betrifft die Verwendung substituierter 2-Amidobenzimidazole, 2- Amidobenzoxazoie und 2-Amidobenzothiazole oder jeweils deren Salze als Wirkstoffe zur Steigerung der Stresstoleranz in Pflanzen gegenüber abiotischem Stress, insbesondere zur Stärkung des Pflanzenwachstums und/oder zur Erhöhung des Pflanzenertrags. Es ist bekannt, dass bestimmte substituierte Benzimidazole als The invention relates to the use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoie and 2-amidobenzothiazoles or their salts as active ingredients for increasing the stress tolerance in plants to abiotic stress, in particular for strengthening the plant growth and / or to increase the plant yield. It is known that certain substituted benzimidazoles as
Schädlingsbekämpfungsmittel eingesetzt (vgl. W094/1 1349) und dass bestimmte Haloalkyl-substituierte 2-Amidobenzimidazole als Wirkstoffe gegen abiotischen Pflanzenstress verwendet werden können (vgl. WO201 1 107504). Es ist außerdem bekannt, dass substituierte Amidobenzimidazoie als pharmazeutische Wirkstoffe (vgl. WO2000029384 und WO2000026192) und für kosmetische  Pesticides used (see W094 / 1 1349) and that certain haloalkyl-substituted 2-Amidobenzimidazole can be used as active ingredients against abiotic plant stress (see WO201 1 107504). It is also known that substituted amidobenzimidazoie as pharmaceutical agents (see WO2000029384 and WO2000026192) and cosmetic
Anwendungen verwendet werden können (vgl. WO2001082877). WO97/04771 beschreibt ebenfalls die pharmazeutische Verwendung von vorwiegend Aryl- substituierten Benzimidazolen, während in WO2000032579 Heterocyclyl-substituierte Benzimidazole beschrieben werden. Die Herstellung von Heterocyclyl-substituierten Benzimidazolen und ihre inhibierende Wirkung an Enzymen aus der Familie der Poly(ADP-ribose)polymerase wird beispielsweise in Org. Proc. Res Devel. 2007, 11 , 693; J. Med. Chem. 2009, 52, 1619 und in J. Med. Chem. 2009, 52, 514 beschrieben, während in J. Med. Chem. 2010, 53, 3142 Herstellungsmethoden zur Bereitstellung von speziellen Aryl-substituierten Benzimidazolen aufgeführt werden. Applications can be used (see WO2001082877). WO97 / 04771 also describes the pharmaceutical use of predominantly aryl-substituted benzimidazoles, while in WO2000032579 heterocyclyl-substituted benzimidazoles are described. The preparation of heterocyclyl-substituted benzimidazoles and their inhibiting action on enzymes from the family of the poly (ADP-ribose) polymerase is described, for example, in Org. Proc. Res Devel. 2007, 11, 693; J. Med. Chem. 2009, 52, 1619 and J. Med. Chem. 2009, 52, 514, while J. Med. Chem. 2010, 53, 3142 disclose methods of preparation for providing specific aryl-substituted benzimidazoles ,
In WO2010083220, W0199524379 und US20090197863 werden substituierte 2- Amidobenzoxazole als pharmazeutische Wirkstoffe und Chemotherapeutika In WO2010083220, WO199524379 and US20090197863 are substituted 2-amidobenzoxazoles as pharmaceutical agents and chemotherapeutic agents
beschrieben. Die Verwendung von substituierten 2-Amidobenzoxazolen als antivirale Wirkstoffe zur Behandlung von Hepatitis C ist ebenfalls bekannt (WO201 1047390). Außerdem werden in der Literatur verschiedene 2-substituierte Benzoxazole als 5-HT3- Rezeptorantagonisten beschrieben (vgl. Bioorg. Med. Chem. Lett. 2010, 20, 6538). Die Herstellung von bestimmten substituierten Benzoxazolen und Benzothiazolen und ihre cytostatische Wirkung wird in Bioorg. Med. Chem. Lett. 2006, 14, 6106 beschrieben. Von den erfindungsgemäßen Amidobenzoxazolen und -thiazolen ist dagegen die Verwendung zur Steigerung der Stresstoleranz in Pflanzen gegenüber abiotischem Stress, zur Stärkung des Pflanzenwachstums und/oder zur Erhöhung des described. The use of substituted 2-amidobenzoxazoles as antiviral agents for the treatment of hepatitis C is also known (WO201 1047390). In addition, various 2-substituted benzoxazoles are described in the literature as 5-HT3 receptor antagonists (compare Bioorg.Med.Chem.Lat., 2010, 20, 6538). The preparation of certain substituted benzoxazoles and benzothiazoles and their cytostatic activity is described in Bioorg. Med. Chem. Lett. 2006, 14, 6106. By contrast, the amidobenzoxazoles and -thiazoles according to the invention are used for increasing the stress tolerance in plants to abiotic stress, for strengthening plant growth and / or for increasing the plant growth
Pflanzenertrags nicht beschrieben. Es ist außerdem bekannt, dass substituierte 2-Amidobenzothiazole als Plant yield not described. It is also known that substituted 2-amidobenzothiazoles as
pharmazeutische Wirkstoffe verwendet werden können (vgl. WO2010083199). pharmaceutical active ingredients can be used (see WO2010083199).
Es ist bekannt, dass Pflanzen auf natürliche Stressbedingungen, wie beispielsweise Kälte, Hitze, Trockenheit, Verwundung, Pathogenbefall (Viren, Bakterien, Pilze, Insekten) etc. aber auch auf Herbizide mit spezifischen oder unspezifischen It is known that plants on natural stress conditions, such as cold, heat, drought, wounding, pathogens (viruses, bacteria, fungi, insects) etc. but also on herbicides with specific or nonspecific
Abwehrmechanismen reagieren [Pflanzenbiochemie, S. 393-462 , Spektrum Defense Mechanisms Respond [Plant Biochemistry, pp. 393-462, Spektrum
Akademischer Verlag, Heidelberg, Berlin, Oxford, Hans W. Heidt, 1996.; Biochemistry and Molecular Biology of Plants, S. 1 102-1203, American Society of Plant Academic Publisher, Heidelberg, Berlin, Oxford, Hans W. Heidt, 1996; Biochemistry and Molecular Biology of Plants, p. 1 102-1203, American Society of Plant
Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000]. Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000].
In Pflanzen sind zahlreiche Proteine und die sie codierenden Gene bekannt, die an Abwehrreaktionen gegen abiotischen Stress (z.B. Kälte, Hitze, Trockenheit, Salz, Überflutung) beteiligt sind. Diese gehören teilweise zu Signaltransduktionsketten (z.B. Transkriptionsfaktoren, Kinasen, Phosphatasen) oder bewirken eine physiologische Antwort der Pflanzenzelle (z.B. lonentransport, Entgiftung reaktiver Sauerstoff- Spezies). Zu den Signalkettengenen der abiotischen Stressreaktion gehören u.a. In plants, numerous proteins and the genes encoding them are involved, which are involved in abiotic stress defense reactions (e.g., cold, heat, drought, salt, flooding). These partially belong to signal transduction chains (e.g., transcription factors, kinases, phosphatases) or cause a physiological response of the plant cell (e.g., ion transport, detoxification of reactive oxygen species). The signal chain genes of the abiotic stress reaction include, among others.
Transkriptionsfaktoren der Klassen DREB und CBF (Jaglo-Ottosen et al., 1998, Science 280: 104-106). An der Reaktion auf Salzstress sind Phosphatasen vom Typ AT PK und MP2C beteiligt. Ferner wird bei Salzstress häufig die Biosynthese von Osmolyten wie Prolin oder Sucrose aktiviert. Beteiligt sind hier z.B. die Sucrose- Synthase und Prolin-Transporter (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol Biol 51 : 463-499). Die Stressabwehr der Pflanzen gegen Kälte und Transcription factors of classes DREB and CBF (Jaglo-Ottosen et al., 1998, Science 280: 104-106). The salt stress response involves AT PK and MP2C phosphatases. Furthermore, in salt stress the biosynthesis of osmolytes such as proline or sucrose is often activated. Involved here are e.g. sucrose synthase and proline transporters (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol Biol 51: 463-499). The stress control of plants against cold and
Trockenheit benutzt z.T. die gleichen molekularen Mechanismen. Bekannt ist die Akkumulation von sogenannten Late Embryogenesis Abundant Proteins (LEA- Proteine), zu denen als wichtige Klasse die Dehydrine gehören (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 100: 291-296). Es handelt sich dabei um Chaperone, die Vesikel, Proteine und Membranstrukturen in gestressten Pflanzen stabilisieren (Bray, 1993, Plant Physiol 103: 1035-1040). Außerdem erfolgt häufig eine Induktion von Aldehyd-Dryness partly uses the same molecular mechanisms. The accumulation of so-called late embryogenesis abundant protein (LEA) is known. Proteins), which include the dehydrins as an important class (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 100: 291-296). These are chaperones that stabilize vesicles, proteins and membrane structures in stressed plants (Bray, 1993, Plant Physiol 103: 1035-1040). In addition, induction of aldehyde
Deydrogenasen, welche die bei oxidativem Stress entstehenden reaktiven Sauerstoff- Spezies (ROS) entgiften (Kirch et al., 2005, Plant Mol Biol 57: 315-332). De-dehydrogenases which detoxify the reactive oxygen species (ROS) produced by oxidative stress (Kirch et al., 2005, Plant Mol Biol 57: 315-332).
Heat Shock Faktoren (HSF) und Heat Shock Proteine (HSP) werden bei Hitzestress aktiviert und spielen hier als Chaperone eine ähnliche Rolle wie die Dehydrine bei Kälte- und Trockenstress (Yu et al., 2005, Mol Cells 19: 328-333). Heat Shock Factors (HSF) and Heat Shock Proteins (HSP) are activated by heat stress and act as chaperones in a similar role to dehydrins in cold and dry stress (Yu et al., 2005, Mol Cells 19: 328-333).
Eine Reihe pflanzenendogener Signalstoffe, die in die Stresstoleranz bzw. die A series of plant endogenous signaling substances that are in the stress tolerance or the
Pathogenabwehr involviert sind, sind bereits bekannt. Zu nennen sind hier Pathogen defense are already known. To call here are
beispielsweise Salicylsäure, Benzoesäure, Jasmonsäure oder Ethylen [Biochemistry and Molecular Biology of Plants, S. 850-929, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000]. Einige dieser for example, salicylic acid, benzoic acid, jasmonic acid or ethylene [Biochemistry and Molecular Biology of Plants, pp. 850-929, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000]. Some of these
Substanzen oder deren stabile synthetische Derivate und abgeleitete Strukturen sind auch bei externer Applikation auf Pflanzen oder Saatgutbeizung wirksam und aktivieren Abwehrreaktionen, die eine erhöhte Stress- bzw. Pathogentoleranz der Pflanze zur Folge haben [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589]. Substances or their stable synthetic derivatives and derived structures are also effective in external application to plants or seed dressing and activate defense reactions that result in an increased stress or pathogen tolerance of the plant [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589].
Es ist weiter bekannt, dass chemische Substanzen die Toleranz von Pflanzen gegen abiotischen Stress erhöhen können. Derartige Substanzen werden dabei entweder durch Saatgut-Beizung, durch Blattspritzung oder durch Bodenbehandung appliziert. So wird eine Erhöhung der abiotischen Stresstoleranz von Kulturpflanzen durch Behandlung mit Elicitoren der Systemic Acquired Resistance (SAR) oder It is also known that chemical substances can increase the tolerance of plants to abiotic stress. Such substances are applied either by seed dressing, by foliar spraying or by soil treatment. Thus, increasing the abiotic stress tolerance of crops by treatment with systemic acquired resistance (SAR) or
Abscisinsäure-Derivaten beschrieben (Schading and Wei, WO-200028055, Abrams and Gusta, US-5201931 , Churchill et al., 1998, Plant Growth Regul 25: 35-45) oder Azibenzolar-S-methyl. Auch bei Anwendung von Fungiziden, insbesondere aus der Gruppe der Strobilurine oder der Succinat Dehydrogenase Inhibitoren werden ähnliche Effekte beobachtet, die häufig auch mit einer Ertragssteigerung einhergehen (Draber et al., DE-3534948, Bartlett et al., 2002, Pest Manag Sei 60: 309). Es ist ebenfalls bekannt, dass das Herbizid Glyphosat in niedriger Dosierung das Wachstum einiger Pflanzenarten stimuliert (Cedergreen, Env. Pollution 2008, 156, 1099). Abscisic acid derivatives (Schading and Wei, WO200028055, Abrams and Gusta, US 5201931, Churchill et al., 1998, Plant Growth Regul 25: 35-45) or azibenzolar-S-methyl. Even with the use of fungicides, in particular from the group of strobilurins or succinate dehydrogenase inhibitors similar effects are observed, which are often associated with an increase in yield (Draber et al., DE-3534948, Bartlett et al., 2002, Pest Manag Sei 60 : 309). It is too It is known that the herbicide glyphosate in low dosage stimulates the growth of some plant species (Cedergreen, Env. Pollution 2008, 156, 1099).
Desweiteren wurden Effekte von Wachstumsregulatoren auf die Stresstoleranz von Kulturpflanzen beschrieben (Morrison and Andrews, 1992, J Plant Growth Regul 1 1 : 1 13-1 17, RD-259027). Bei osmotischem Stress ist eine Schutzwirkung durch Furthermore, effects of growth regulators on the stress tolerance of crop plants have been described (Morrison and Andrews, 1992, J Plant Growth Regul 1 1: 1 13-1 17, RD-259027). When osmotic stress is a protective effect through
Applikation von Osmolyten wie z.B. Glycinbetain oder deren biochemischen Vorstufen, z.B. Cholin-Derivate beobachtet worden (Chen et al., 2000, Plant Cell Environ 23: 609- 618, Bergmann et al., DE-4103253). Auch die Wirkung von Antioxidantien wie z.B Naphtole und Xanthine zur Erhöhung der abiotischen Stresstoleranz in Pflanzen wurde bereits beschrieben (Bergmann et al., DD-277832, Bergmann et al., DD-277835). Die molekularen Ursachen der Anti-Stress-Wirkung dieser Substanzen sind jedoch weitgehend unbekannt. Es ist weiter bekannt, dass die Toleranz von Pflanzen gegenüber abiotischem Stress durch eine Modifikation der Aktivität von endogenen Poly-ADP-ribose Polymerasen (PARP) oder Poly-(ADP-ribose) glycohydrolasen (PARG) erhöht werden kann (de Block et al., The Plant Journal, 2005, 41 , 95; Levine et al., FEBS Lett. 1998, 440, 1 ; WO0004173; WO04090140). Application of osmolytes, e.g. Glycine betaine or its biochemical precursors, e.g. Choline derivatives have been observed (Chen et al., 2000, Plant Cell Environ 23: 609-618, Bergmann et al., DE-4103253). The action of antioxidants such as naphtols and xanthines to increase the abiotic stress tolerance in plants has also been described (Bergmann et al., DD-277832, Bergmann et al., DD-277835). However, the molecular causes of the anti-stress effects of these substances are largely unknown. It is further known that the tolerance of plants to abiotic stress can be increased by a modification of the activity of endogenous poly-ADP-ribose polymerases (PARP) or poly (ADP-ribose) glycohydrolases (PARG) (de Block et al. , The Plant Journal, 2005, 41, 95; Levine et al., FEBS Lett. 1998, 440, 1, WO0004173, WO04090140).
Somit ist bekannt, dass Pflanzen über mehrere endogene Reaktionsmechanismen verfügen, die eine wirksame Abwehr gegenüber verschiedensten Schadorganismen und/oder natürlichem abiotischen Stress bewirken können. Da sich aber die ökologischen und ökonomischen Anforderungen an moderne Thus, it is known that plants have a number of endogenous reaction mechanisms that can effect effective defense against a variety of harmful organisms and / or natural abiotic stress. But since the ecological and economic requirements of modern
Pflanzenbehandlungsmittel laufend erhöhen, beispielsweise was Toxizität, Selektivität, Aufwandmenge, Rückstandsbildung und günstige Herstellbarkeit angeht, besteht die ständige Aufgabe neue Pflanzenbehandlungsmittel zu entwickeln, die zumindest in Teilbereichen Vorteile gegenüber den bekannten aufweisen.  Constantly increase plant treatment, for example, as regards toxicity, selectivity, application rate, residue formation and cheap manufacturability, there is the constant task of developing new plant treatment agents that have advantages over the known at least in some areas.
Daher bestand die Aufgabe der vorliegenden Erfindung darin, weitere Verbindungen bereitzustellen, die die Toleranz gegenüber abiotischem Stress in Pflanzen erhöhen. Gegenstand der vorliegenden Erfindung ist demnach die Verwendung substituierter 2- Amidobenzimidazole, 2-Amidobenzoxazole und 2-Amidobenzothiazole der Therefore, the object of the present invention was to provide further compounds which increase the tolerance to abiotic stress in plants. The present invention accordingly provides for the use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles
allgemeinen Formel (I) oder deren Salze general formula (I) or salts thereof
zur Toleranzerhöhung gegenüber abiotischem Stress in Pflanzen, wobei to increase tolerance to abiotic stress in plants, wherein
R1, R2, R3 unabhängig voneinander für Wasserstoff, Halogen, Alkyl, Cycloalkyl, R 1 , R 2 , R 3 independently of one another represent hydrogen, halogen, alkyl, cycloalkyl,
Cycloalkenyl, Halocycloalkyl, Alkenyl, Alkinyl, Aryl, Arylalkyl, Arylalkenyl, Heteroaryl, Heteroarylalkyl, Heterocyclyl, Heterocyclylalkyl, Alkoxyalkyl, Alkylthio, Haloalkylthio, Haloalkyl, Alkoxy, Haloalkoxy, Cycloalkoxy,  Cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy,
Cycloalkylalkoxy, Aryloxy, Heteroraryloxy, Alkoxyalkoxy, Alkinylalkoxy,  Cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy,
Alkenyloxy, Bis-alkylaminoalkoxy, Tris-[alkyl]silyl, Bis-[alkyl]arylsilyl, Bis- [alkyl]alkylsilyl, Tris-[alkyl]silylalkinyl, Arylalkinyl, Heteroarylalkinyl, Alkylalkinyl, Cycloalkylalkinyl, Haloalkylalkinyl, Heterocyclyl-N-alkoxy, Nitro, Cyano, Amino, Alkylamino, Bis-alkylamino, Alkylcarbonylamino, Cycloalkylcarbonylamino, Arylcarbonylamino, Alkoxycarbonylamino, Heteroarylalkoxy, Arylalkoxy, Heterocyclylalkoxy, Cycloalkylalkyl, Haloalkenyl, Haloalkinyl,  Alkenyloxy, bis-alkylaminoalkoxy, tris [alkyl] silyl, bis [alkyl] arylsilyl, bis [alkyl] alkylsilyl, tris [alkyl] silylalkynyl, arylalkynyl, heteroarylalkynyl, alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-N-alkoxy, Nitro, cyano, amino, alkylamino, bis-alkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, heteroarylalkoxy, arylalkoxy, heterocyclylalkoxy, cycloalkylalkyl, haloalkenyl, haloalkynyl,
Heterocyclylalkinyl, Halocycloalkoxy, Haloalkinyloxy, Arylthio, Heteroarylthio, Alkylsulfinyl, Haloalkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, Alkylsulfonyl, Haloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, Thiocyanato, Isothiocyanato, Cycloalkylamino, Cycloalkyl(alkyl)amino, Alkenylamino stehen,  Heterocyclylalkynyl, halocycloalkoxy, haloalkynyloxy, arylthio, heteroarylthio, alkylsulfinyl, haloalkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, thiocyanato, isothiocyanato, cycloalkylamino, cycloalkyl (alkyl) amino, alkenylamino,
R1 und R2 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, R 1 and R 2 with the atoms to which they are attached form a completely saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring,
R2 und R3 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, R 2 and R 3 with the atoms to which they are attached, a fully saturated, form part-saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring,
W für Sauerstoff, Schwefel steht, W stands for oxygen, sulfur,
X für Sauerstoff, Schwefel, N-R4 steht, X is oxygen, sulfur, NR 4 ,
R4 für Wasserstoff, Alkyl, Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl, Cyanoalkyl,R 4 is hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cyanoalkyl,
Alkenylalkyl, Haloalkyl, Alkinylalkyl, Arylalkyl, Heteroarylalkyl, Heterocyclylalkyl, Alkylcarbonyl, Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, Alkenylalkyl, haloalkyl, alkynylalkyl, arylalkyl, heteroarylalkyl, heterocyclylalkyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl,
Haloalkylcarbonyl, Heterocyclylcarbonyl, Arylalkylcarbonyl, Alkoxycarbonyl, Cycloalkylalkoxycarbonyl, Cycloalkoxycarbonyl, Alkoxycarbonylalkyl,  Haloalkylcarbonyl, heterocyclylcarbonyl, arylalkylcarbonyl, alkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkoxycarbonyl, alkoxycarbonylalkyl,
Alkylsulfonyl, Cycloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl,  Alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl,
Alkoxycarbonylcarbonyl, Arylalkoxycarbonylcarbonyl, Alkylaminothiocarbonyl, Alkylaminocarbonyl, Cycloalkylaminocarbonyl, Alkoxyalkyl, Bis- [Alkyl]aminocarbonyl, Aryl, Heteroaryl, Heterocyclyl, Cycloalkoxycarbonylalkyl steht,  Alkoxycarbonylcarbonyl, arylalkoxycarbonylcarbonyl, alkylaminothiocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, alkoxyalkyl, bis- [alkyl] aminocarbonyl, aryl, heteroaryl, heterocyclyl, cycloalkoxycarbonylalkyl,
Q für Alkyl, Alkenyl, Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl, Aryl, Arylalkyl, Q is alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, aryl, arylalkyl,
Heteroarylalkyl, Heterocyclylalkyl, Heteroaryl, Heterocyclyl, Heterocyclylaryl, Heterocyclylheteroaryl, Heteroarylheteroaryl, Heteroarylaryl, Arylaryl,  Heteroarylalkyl, heterocyclylalkyl, heteroaryl, heterocyclyl, heterocyclylaryl, heterocyclylheteroaryl, heteroarylheteroaryl, heteroarylaryl, arylaryl,
Aryloxyaryl, Arylalkenyl, Heteroarylalkenyl, Heterocyclylalkenyl, Arylalkinyl, Heteroarylalkinyl, Heterocyclylalkinyl, Cycloalkylalkinyl, Alkylaminoalkyl, Bis- alkylaminoalkyl, Hydroxyalkyl, Alkoxyalkyl, Tris-[alkyl]silyloxyalkyl, Bis- [alkyl]arylsilyloxyalkyl, Bis-[alkyl]alkylsilyloxyalkyl, Bis-alkylaminoalkoxyalkyl, Alkoxyalkoxyalkyl, Aryloxyalkyl, Heteroaryloxyalkyl, Alkylthioalkyl, Arylthioalkyl, Heteroarylthioalkyl, Alkoxycarbonyl-N-heterocyclyl, Arylalkoxycarbonyl-N- heterocyclyl, Alkyl-N-heterocyclyl, Alkylsulfonyl-N-heterocyclyl, Arylsulfonyl-N- heterocyclyl, Heteroarylsulfonyl-N-heterocyclyl, Cycloalkylsulfonyl-N- heterocyclyl, Haloalkylsulfonyl-N-heterocyclyl, Alkylcarbonyl-N-heterocyclyl, Arylcarbonyl-N-heterocyclyl, Heteroarylcarbonyl-N-heterocyclyl,  Aryloxyaryl, arylalkenyl, heteroarylalkenyl, heterocyclylalkenyl, arylalkynyl, heteroarylalkynyl, heterocyclylalkynyl, cycloalkylalkynyl, alkylaminoalkyl, bisalkylaminoalkyl, hydroxyalkyl, alkoxyalkyl, tris [alkyl] silyloxyalkyl, bis [alkyl] arylsilyloxyalkyl, bis [alkyl] alkylsilyloxyalkyl, bis-alkylaminoalkoxyalkyl , Alkoxyalkoxyalkyl, aryloxyalkyl, heteroaryloxyalkyl, alkylthioalkyl, arylthioalkyl, heteroarylthioalkyl, alkoxycarbonyl-N-heterocyclyl, arylalkoxycarbonyl-N-heterocyclyl, alkyl-N-heterocyclyl, alkylsulfonyl-N-heterocyclyl, arylsulfonyl-N-heterocyclyl, heteroarylsulfonyl-N-heterocyclyl, cycloalkylsulfonyl -N-heterocyclyl, haloalkylsulfonyl-N-heterocyclyl, alkylcarbonyl-N-heterocyclyl, arylcarbonyl-N-heterocyclyl, heteroarylcarbonyl-N-heterocyclyl,
Cycloalkylcarbonyl-N-heterocyclyl, Cycloalkyl-N-heterocyclyl, Aryl-N- heterocyclyl, Arylalkyl-N-heterocyclyl, Bis-alkylaminoalkyl-N-heterocyclyl, Bis- alkylaminosu!fonyl-N-heterocyclyl, Heteroaryloxyaryl, Heteroaryloxyheteroaryl, Aryloxyheteroaryl, Alkylsulfinyl, Alkylthio, Alkylsulfonyl, CycloalkySsuSfinyl, Cycloalkylthio, Cycloalkylsulfonyl, Arylsulfinyl, Arylthio, Arylsulfonyl, Amino, Alkylamino, Arylamino, Arylalkylamino, Cycloalkylamino, Formyl, Alkylcarbonyl, Arylcarbonyl, Iminoalkyl, Alkyliminoalkyl, Aryliminoalkyl, Alkoxycarbonyl, Cycloalkylcarbonyl-N-heterocyclyl, cycloalkyl-N-heterocyclyl, aryl-N-heterocyclyl, arylalkyl-N-heterocyclyl, bis-alkylaminoalkyl-N-heterocyclyl, bis- alkylaminosulfonyl-N-heterocyclyl, heteroaryloxyaryl, heteroaryloxyheteroaryl, aryloxyheteroaryl, alkylsulfinyl, alkylthio, alkylsulfonyl, cycloalkylsulfinyl, cycloalkylthio, cycloalkylsulfonyl, arylsulfinyl, arylthio, arylsulfonyl, amino, alkylamino, arylamino, arylalkylamino, cycloalkylamino, formyl, alkylcarbonyl, arylcarbonyl, iminoalkyl, Alkyliminoalkyl, aryliminoalkyl, alkoxycarbonyl,
Cycloalkoxycarbonyl, Cycloalkylalkoxycarbonyl, Arylalkoxycarbonyl, Cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, arylalkoxycarbonyl,
Arylalkylaminocarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Arylalkylaminocarbonyl, aminocarbonyl, alkylaminocarbonyl,
Cycloalkylaminocarbonyl, Bis-alkylaminocarbonyl Heterocyclyl-N-carbonyl, Imino, Alkylimino, Arylimino, Cycloalkylimino, Cycloalkylalkylimino, Cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heterocyclyl-N-carbonyl, imino, alkylimino, arylimino, cycloalkylimino, cycloalkylalkylimino,
Hydroxyimino, Alkoxyimino, Cycloalkoxyimino, Cyloalkylalkoxyimino, Hydroxyimino, alkoxyimino, cycloalkoxyimino, cycloalkylalkoxyimino,
Heteroaryloxyimino, Aryloxyimino, Arylalkoxyimino, Alkenyloxyimino, Heteroaryloxyimino, aryloxyimino, arylalkoxyimino, alkenyloxyimino,
Heteroarylalkoxyimino, Heteroarylimino, Heterocyclylimino, Heteroarylalkoxyimino, heteroarylimino, heterocyclylimino,
Heterocyclylalkylimino, Aminoimino, Alkylaminoimino, Arylaminoimino, Heterocyclylalkylimino, aminoimino, alkylaminoimino, arylaminoimino,
Heteroarylaminoimino, Cycloalkylaminoimino, Bis-Alkylaminoimino, Heteroarylaminoimino, cycloalkylaminoimino, bis-alkylaminoimino,
Arylalkylaminoimino, Aryl(alkyl)aminoimino, Cycloalkyl(alkyl)aminoimino, Cycloalkylalkylaminoimino, Heterocyclylaminoimino, Heteroarylalkoxyalkyl, Arylalkoxyalkyl, Heterocyclyl-N-alkyl, Aryl(alkyl)aminoalkyl, Arylalkylaminoimino, aryl (alkyl) aminoimino, cycloalkyl (alkyl) aminoimino, cycloalkylalkylaminoimino, heterocyclylaminoimino, heteroarylalkoxyalkyl, arylalkoxyalkyl, heterocyclyl-N-alkyl, aryl (alkyl) aminoalkyl,
Arylalkyl(alkyl)aminoalkyl, Alkoxycarbonylalkylaminoalkyl, Arylalkyl (alkyl) aminoalkyl, alkoxycarbonylalkylaminoalkyl,
Alkoxycarbonylalkyl(alkyl)aminoalkyl, Heteroaryl(alkyl)aminoalkyl, Alkoxycarbonylalkyl (alkyl) aminoalkyl, heteroaryl (alkyl) aminoalkyl,
Heteroarylalkyl(alkyl)aminoalkyl, Cycloalkyl(alkyl)aminoalkyl, Heteroarylalkyl (alkyl) aminoalkyl, cycloalkyl (alkyl) aminoalkyl,
Cycloalkylaminoalkyl, Alkoxy(alkoxy)alkyl, Arylalkoxyalkylaryl, Heterocyclyl-N- alkylaryl, Aryl(alkyl)aminoalkylaryl, Arylalkyl(alkyl)aminoalkylaryl, Cycloalkylaminoalkyl, alkoxy (alkoxy) alkyl, arylalkoxyalkylaryl, heterocyclyl-N-alkylaryl, aryl (alkyl) aminoalkylaryl, arylalkyl (alkyl) aminoalkylaryl,
Alkoxycarbonylalkylaminoalkylaryl, Alkoxycarbonylalkyl(alkyl)aminoalkylaryl, Heteroaryl(alkyl)aminoalkylaryl, Heteroarylalkyl(alkyl)aminoalkylaryl, Alkoxycarbonylalkylaminoalkylaryl, alkoxycarbonylalkyl (alkyl) aminoalkylaryl, heteroaryl (alkyl) aminoalkylaryl, heteroarylalkyl (alkyl) aminoalkylaryl,
Cycloalkyl(alkyl)aminoalkylaryl, Cycloalkylaminoalkylaryl, Alkoxy(alkoxy)alkylaryl steht, zusätzlich, wenn X für ein Sauerstoffatom oder X für ein Schwefelatom steht, für Haloalkyl, Alkoxyhaloalkyl, Halocycloalkyl, Haloalkoxyhaloalkyl, Arylhaloalkyl, Alkylthiohaloalkyl, Bisalkylaminoalkoxyhaloalkyl steht, für Wasserstoff, Hydroxy, Alkyl, Cycloalkyl, Halocycloalkyl, Halogen, Cycloalkyl (alkyl) aminoalkylaryl, cycloalkylaminoalkylaryl, alkoxy (alkoxy) alkylaryl, additionally, when X is an oxygen atom or X is a sulfur atom, is haloalkyl, alkoxyhaloalkyl, halocycloalkyl, haloalkoxyhaloalkyl, arylhaloalkyl, alkylthiohaloalkyl, bisalkylaminoalkoxyhaloalkyl, hydrogen, hydroxy, Alkyl, cycloalkyl, halocycloalkyl, halogen,
Alkenylalkyl, Haloalkyl, Alkinyl, Alkenyl, Cyanoalkyl, Nitroalkyl, Aminoalkyl, Alkylaminoalkyl, Bis-[Alkyl]aminoalkyl, Alkinylalkyl, Arylalkyl, Heteroarylalkyl, Heterocyclylalkyl, Alkylcarbonyl, Alkoxycarbonyl, Cycloalkoxycarbonyl, Alkenylalkyl, haloalkyl, alkynyl, alkenyl, cyanoalkyl, nitroalkyl, aminoalkyl, alkylaminoalkyl, bis [alkyl] aminoalkyl, alkynylalkyl, arylalkyl, heteroarylalkyl, Heterocyclylalkyl, alkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl,
Alkylsulfonyl, ArylsulfonyS, Heteroarylsulfonyl, Cycloalkylsulfonyl, Alkylsulfinyl, Arylsulfinyl, Cycloalkylsulfinyl, Alkoxycarbonylalkyl, Aryl, Heteroaryl,  Alkylsulfonyl, arylsulfonyS, heteroarylsulfonyl, cycloalkylsulfonyl, alkylsulfinyl, arylsulfinyl, cycloalkylsulfinyl, alkoxycarbonylalkyl, aryl, heteroaryl,
Heterocyclyl, Aminocarbonylalkyl, Alkylaminocarbonylalkyl,  Heterocyclyl, aminocarbonylalkyl, alkylaminocarbonylalkyl,
Bisalkylaminocarbonylalkyl, Cycloalkylaminocarbonylalkyl,  Bisalkylaminocarbonylalkyl, cycloalkylaminocarbonylalkyl,
Hydroxycarbonylalkyl, Amino, Alkylamino, Arylamino, Alkoxy, Cycloalkylalkyl steht und  Hydroxycarbonylalkyl, amino, alkylamino, arylamino, alkoxy, cycloalkylalkyl and
Z2 für Wasserstoff, Alkyl, Cycloalkyl, verzweigtes oder unverzweigtes Haiogenalkyl, Aikinyl, Alkenyl, Cyanoalkyl, Arylalkyl, Heteroarylalkyl, Alkylcarbonyl, Z 2 is hydrogen, alkyl, cycloalkyl, branched or unbranched haloalkyl, aikinyl, alkenyl, cyanoalkyl, arylalkyl, heteroarylalkyl, alkylcarbonyl,
Alkoxycarbonyl steht oder  Alkoxycarbonyl is or
Z1 und Z2 zusammen mit dem Atomen, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome Z 1 and Z 2 together with the atom to which they are attached, a fully saturated or partially saturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden oder  form interrupted and optionally further substituted 5 to 7-membered ring or
Z1 und Z2 zusammen Bestandteil einer gegebenenfalls substituierten Sulfilimin- oder Amidingruppe sind oder ein Iminophosphoran bilden. Z 1 and Z 2 together are part of an optionally substituted Sulfilimin- or amidine group or form a iminophosphorane.
Die Verbindungen der allgemeinen Formel (I) können durch Anlagerung einer geeigneten anorganischen oder organischen Säure, wie beispielsweise Mineralsäuren, wie beispielsweise HCl, HBr, H2SO4, H3PO4 oder HNO3, 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 oder Carbonsäuren, vorliegen, können innere Salze mit ihrerseits protonierbaren Gruppen, wie Aminogruppen bilden. The compounds of general formula (I) may be prepared by addition of a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3, or organic acids, e.g. For example, 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 which are in deprotonated form, such as Sulfonic acids or carboxylic acids, may form internal salts with their turn protonatable groups, such as amino groups.
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)".
Bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der allgemeinen Formel (I), worin R1 , R2, R3 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C8)-Alkyl, (C3-C8)- Cycloalkyl, (C4-C8)-Cycloalkenyl, (C3-C8)-Halocycloalkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C8)-alkyl, Aryl- (C2-C8)-alkenyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl- (Ci-Cs)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (d-C8)-Alkylthio, (Ci-C8)- Haloalkylthio, (Ci-C8)-Haloalkyl, (Ci-C8)-Alkoxy, (Ci-C8)-Haloalkoxy, (C3-C8)-Cycloalkyl, (-, the inventive use of compounds of general formula (I) wherein R 1, R 2, R 3 are independently hydrogen, halogen, (Ci-C 8) -alkyl, (C 3 -C 8) is preferably C 4 -C 8) cycloalkenyl, (C 3 -C 8) halocycloalkyl, (C 2 -C 8) alkenyl, (C2-C8) -alkynyl, optionally substituted phenyl, aryl (Ci-C 8) -alkyl, aryl- (C 2 -C 8 ) -alkenyl, heteroaryl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (Ci -C 8) alkyl, (dC 8) alkylthio, (Ci-C 8) - haloalkylthio, (Ci-C 8) haloalkyl, (Ci-C 8) alkoxy, (Ci-C8) haloalkoxy, (C 3 -C 8 ) -
Cycloalkoxy, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxy, Aryloxy, Heteroraryloxy, Cycloalkoxy, (C 3 -C 8) cycloalkyl (Ci-C8) alkoxy, aryloxy, Heteroraryloxy,
(Ci-C8)-Alkoxy-(Ci-C8)-alkoxy, (C2-C8)-Alkinyl-(Ci-C8)-alkoxy, (C2-C8)- Alkenyloxy, Bis-[(Ci-C8)-alkyl]amino-(Ci-C8)-alkoxy, Tris-[(Ci-C8)-alkyl]silyl, Bis- [(Ci-C8)-alkyl]arylsilyl, Bis-[(Ci-C8)-alkyl]-(Ci-C8)-alkylsilyl, Tris-[(Ci-C8)- alkyl]silyl-(C2-C8)-alkinyl, Aryl-(C2-C8)-alkinyl, Heteroaryl-(C2-C8)-alkinyl, (Ci-C8)-(Ci-C 8) alkoxy (Ci-C 8) alkoxy, (C 2 -C 8) alkynyl (Ci-C 8) alkoxy, (C 2 -C 8) - alkenyloxy, bis [ (C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkoxy, tris - [(C 1 -C 8 ) -alkyl] silyl, bis [(C 1 -C 8 ) -alkyl] arylsilyl, bis- [(Ci-C 8) alkyl] - (Ci-C8) alkylsilyl, tris - [(Ci-C 8) - alkyl] silyl (C 2 -C 8) alkynyl, aryl (C 2 - C 8 ) -alkynyl, heteroaryl- (C 2 -C 8 ) -alkynyl, (C 1 -C 8 ) -
Alkyl-(C2-C8)-alkinyl, (C3-C8)-Cycloalkyl-(C2-C8)-alkinyl, (d-C8)-Haloalkyl- (C2-C8)-alkinyl, Heterocyclyl-N-(Ci-C8)-alkoxy, Nitro, Cyano, Amino, (Ci-C8)- Alkylamino, Bis-[(Ci-C8)-alkyl]amino, (Ci-C8)- Alkylcarbonylamino, (C3-C8)- Cycloalkylcarbonylamino, Arylcarbonylamino, (Ci-Cs)-Alkoxycarbonylamino, Heterocyclyl-(Ci-C8)-alkoxy, (C3-C8)- Cycloalkyl-(Ci-C8)-alkyl, (C2-C8)-Alkyl (C 2 -C 8) -alkynyl, (C 3 -C 8) cycloalkyl (C 2 -C 8) -alkynyl, (DC 8) haloalkyl (C 2 -C 8) alkynyl, heterocyclyl -N- (Ci-C 8) alkoxy, nitro, cyano, amino, (Ci-C8) - alkylamino, - bis [(Ci-C 8) alkyl] amino, (Ci-C 8) - alkylcarbonylamino, (C 3 -C 8) - cycloalkylcarbonylamino, arylcarbonylamino, (Ci-Cs) alkoxycarbonylamino, heterocyclyl (Ci-C 8) alkoxy, (C 3 -C 8) - cycloalkyl, (Ci-C 8) alkyl, (C 2 -C 8 ) -
Haloalkenyl, (C2-C8)-Haloalkinyl, Heterocyclyl-(C2-C8)-alkinyl, (C3-C8)- Halocycloalkoxy, (C2-C8)-Haloalkinyloxy, Arylthio, Heteroarylthio, (Ci-C8)- Alkylsulfinyl, (Ci-C8)-Haloalkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, (Ci-C8)- Alkylsulfonyl, (Ci-C8)-Haloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, Haloalkenyl, (C 2 -C 8 ) -haloalkynyl, heterocyclyl- (C 2 -C 8 ) -alkynyl, (C 3 -C 8 ) -halocycloalkoxy, (C 2 -C 8 ) -haloalkynyloxy, arylthio, heteroarylthio, (Ci -C 8) - alkylsulfinyl, (Ci-C8) haloalkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, (Ci-C 8) - alkylsulfonyl, (Ci-C 8) haloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl,
Thiocyanato, Isothiocyanato, (C3-C8)-Cycloalkylamino, (C3-C8)-Thiocyanato, isothiocyanato, (C 3 -C 8 ) -cycloalkylamino, (C 3 -C 8 ) -
Cycloalkyl[(Ci-C8)-alkyl]amino, (C2-C8)-Alkenylamino stehen, Cycloalkyl [(Ci-C 8) alkyl] amino, (C2 -C8) -alkenylamino,
R1 und R2 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, R2 und R3 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome form interrupted and optionally further substituted 5 to 7-membered ring, R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, für Sauerstoff, Schwefel steht,  form interrupted and optionally further substituted 5 to 7-membered ring, represents oxygen, sulfur,
X für Sauerstoff, Schwefel, N-R4 steht, für Wasserstoff, (Ci-C8)-Alkyl, (C3-C8)-Cycloalkyl, (C3-C8)-Cycloalkyl-(Ci-C8)- alkyl, (C4-C8)-Cycloalkenyl, Cyano-(Ci-C8)-alkyl, (C2-C8)-Alkenyl-(Ci-C8)-alkyl, (Ci-C8)-Haloalkyl, (C2-C8)-Alkinyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkyl, Heteroaryl- (d-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl, (C3-C8)- Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, Heterocyclylcarbonyl, Aryl-(Ci-C8)-alkylcarbonyl, (Ci-C8)-Alkoxycarbonyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl, (C3-C8)- Cycloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (Ci-C8)- Alkoxycarbonylcarbonyl, Aryl-(Ci-C8)-alkoxycarbonylcarbonyl, (Ci-C8)- Alkylaminothiocarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C3-C8)- Cycloalkylaminocarbonyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Bis-[(Ci-C8)- Alkyl]aminocarbonyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C8)- Cycloalkoxycarbonyl-(Ci-C8)-alkyl steht, für (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C3-C8)-Cycloalkyl, (C3-C8)-Cycloalkyl-(Ci-C8)- alkyl, (C4-C8)-Cycloalkenyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-Cs)- alkyl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, Heteroaryl, X represents oxygen, sulfur, NR 4, represents hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) cycloalkyl (Ci-C8) - alkyl , (C 4 -C 8) cycloalkenyl, cyano (Ci-C 8) alkyl, (C 2 -C 8) alkenyl (Ci-C 8) alkyl, (Ci-C 8) haloalkyl, (C 2 -C 8) alkynyl (Ci-C 8) alkyl, aryl (Ci-C 8) alkyl, heteroaryl (dC 8) alkyl, heterocyclyl (Ci-C8) alkyl, (Ci-C 8) alkylcarbonyl, (C 3 -C 8) - cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (Ci-C 8) haloalkylcarbonyl, heterocyclylcarbonyl, aryl (Ci-C8) alkylcarbonyl, (Ci-C 8 ) alkoxycarbonyl, (C 3 -C 8) cycloalkyl (Ci-C8) -alkoxycarbonyl, (C 3 -C 8) -cycloalkoxycarbonyl, (Ci-C8) alkoxycarbonyl (Ci-C 8) -alkyl , (Ci-C8) alkylsulfonyl, (C 3 -C 8) - cycloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (Ci-C 8) - alkoxycarbonylcarbonyl, aryl (Ci-C 8) -alkoxycarbonylcarbonyl, (Ci-C 8) - alkylaminothiocarbonyl, (Ci-C 8) alkylaminocarbonyl, (C 3 -C 8) - cycloalkylaminocarbonyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, - bis [(Ci-C 8) - alkyl] aminocarbonyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 8) - cycloalkoxycarbonyl (Ci-C 8) alkyl, is (Ci-C 8) -alkyl, (C 2 -C 8) alkenyl, (C 3 -C 8) -cycloalkyl, (C 3 -C 8) cycloalkyl (Ci-C8) - alkyl, (C 4 -C 8) cycloalkenyl, optionally substituted phenyl, aryl (C -Cs) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl- (C 1 -C 8 ) -alkyl, heteroaryl,
Heterocyclyl, Heterocyclylaryl, Heterocyclylheteroaryl, Heteroarylheteroaryl, Heteroarylaryl, Arylaryl, Aryloxyaryl, Aryl-(C2-C8)-alkenyl, Heteroaryl-(C2-C8)- alkenyl, Heterocyclyl-(C2-C8)-alkenyl, Aryl-(C2-C8)-alkinyl, Heteroaryl-(C2-C8)- alkinyl, Heterocyclyl-(Ci-C8)-alkinyl, (C3-C8)-Cyc!oalkyl-(C2-C8)-alkinyl, (Ci-C8)- Alkylamino-(Ci-C8)-alkyl, Bis-[(Ci-C8)-alkyl]amino-(Ci-C8)-alkyl, Hydroxy- (Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Tris-[(Ci-C8)-alkyl]silyloxy-(Ci-C8)- alkyl, Bis-[(Ci-C8)-alkyl]arylsilyloxy-(Ci-C8)-alkyl, Bis-[(Ci-C8)-alkyl]-(Ci-C8)- alkylsily!oxy-(Ci-C8)-alkyl, Bis-[(Ci-C8)-alkyl]amino-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, Aryloxy-(Ci-C8)-alkyl, Heterocyclyl, heterocyclylaryl, heterocyclylheteroaryl, heteroarylheteroaryl, heteroarylaryl, arylaryl, aryloxyaryl, aryl- (C 2 -C 8 ) -alkenyl, heteroaryl- (C 2 -C 8 ) -alkenyl, heterocyclyl- (C 2 -C 8 ) -alkenyl, aryl- C2-C8) alkynyl, heteroaryl (C 2 -C 8) - alkynyl, heterocyclyl (Ci-C8) -alkynyl, (C 3 -C 8) -Cyc oalkyl- (C 2 -C 8) -alkynyl, (Ci-C8) - alkylamino (Ci-C8) alkyl , Bis - [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkyl, hydroxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) - alkyl, tris - [(Ci-C 8) alkyl] silyloxy (Ci-C 8) - alkyl, - bis [(Ci-C 8) alkyl] arylsilyloxy- (Ci-C 8) -alkyl, bis- [(C 1 -C 8 ) -alkyl] - (C 1 -C 8 ) -alkylsilyloxy- (C 1 -C 8 ) -alkyl, bis - [(C 1 -C 8 ) -alkyl] -amino- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, aryloxy- (C 1 -C 8 ) -alkyl .
Heteroaryloxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, Arylthio-(d-Ce)- alkyl, Heteroarylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkoxycarbonyl-N-heterocyclyl, Aryl- (Ci-C8)-alkoxycarbonyl-N-heterocyclyl, (Ci-C8)-A!kyl-N-heterocyclyl, (d-C8)- Alkylsulfonyl-N-heterocyclyl, Arylsulfonyl-N-heterocyclyl, Heteroarylsulfonyl-N- heterocyclyl, (C3-C8)-Cycloalkylsu!fonyl-N-heterocyclyl, (d-C8)- Haloalkylsulfonyl-N-heterocyclyl, (Ci-C8)-Alkylcarbonyl-N-heterocyclyl, Heteroaryloxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl, arylthio (d-Ce) -alkyl, heteroarylthio (C 1 -C 8 ) -alkyl, ! (Ci-C8) alkoxycarbonyl-N-heterocyclyl, aryl (Ci-C8) alkoxycarbonyl-N-heterocyclyl, (Ci-C 8) -A alkyl-N-heterocyclyl, (dC 8) - alkylsulfonyl N-heterocyclyl, N-heterocyclyl-arylsulfonyl, heteroarylsulfonyl-N-heterocyclyl, (C3-C8) -Cycloalkylsu fonyl-N-heterocyclyl, (dC 8) - haloalkylsulfonyl-N-heterocyclyl, (Ci-C 8) alkylcarbonyl -N-heterocyclyl,
Arylcarbonyl-N-heterocyclyl, Heteroary!carbonyl-N-heterocyclyl, (C3-C8)- Cycloalkylcarbonyl-N-heterocyclyl, (Ci-C8)-Cycloalkyl-N-heterocyclyl, Aryl-N- heterocyclyl, Aryl-(Ci-C8)-alkyl-N-heterocyclyl, Bis-[(Ci-C8)-alkyl]aminoalkyl-N- heterocyclyl, Bis-[(Ci-C8)-alkyl]aminosulfonyl-N-heterocyclyl, Heteroaryloxyaryl, Heteroaryloxyheteroaryl, Aryloxyheteroaryl, (Ci-C8)-Alkylsulfinyl, (Ci-C8)- Alkylthio, (Ci-C8)-Alkylsulfonyl, (C3-C8)-Cycloalkylsulfinyl, (C3-C8)-Cycloalkylthio, (C3-C8)-Cycloalkylsulfonyl, Arylsulfinyl, Arylthio, Arylsulfonyl, Amino, (d-C8)- Alkylamino, Bis-[(Ci-C8)-Alkyl]amino, Arylamino, Aryl-(Ci-C8)-alkylamino, (C3-C8)-Cycloalkylamino, Formyl, (Ci-C8)-Alkylcarbonyl, Arylcarbonyl, Imino- (Ci-Cs)-alkyl, (Ci-C8)-Alkylimino-(Ci-C8)-alkyl, Arylimino-(Ci-C8)-alkyl, (Ci-C8)- Alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (C3-C8)-Cycloa!kyl-(Ci-C8)- alkoxycarbonyl, Aryl-(Ci-C8)-alkoxycarbonyl, Aryl-(Ci-C8)-alkylaminocarbonyl, Aminocarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C3-C8)-Cycloalky!aminocarbonyl, Bis-[(Ci-C8)-alkyl]aminocarbonyl, Heterocyclyl-N-carbonyl, Imino, (Ci-C8)- Alkylimino, Arylimino, (C3-C8)-Cycloalkylimino, (C3-C8)-Cycloalkyl-(Ci-C8)- alkylimino, Hydroxyimino, (Ci-C8)-Alkoxyimino, (C2-C8)-Alkenyloxyimino, (C3-C8)-Cycloalkoxyimino, (C3-C8)-Cyloalkyl-(Ci-C8)-alkoxyimino, Aryloxyimino, Aryl-(Ci-C8)-alkoxyimino, Heteroaryl-(Ci-C8)-alkoxyimino, Heteroaryloxyimino, Heteroarylimino, Heterocyclylimino, Heterocyclyl-(Ci-C8)-alkylimino, ! Arylcarbonyl-N-heterocyclyl, heteroaryl carbonyl-N-heterocyclyl, (C3-C8) - cycloalkyl carbonyl-N-heterocyclyl, (Ci-C 8) -cycloalkyl-N-heterocyclyl, aryl-N- heterocyclyl, aryl (C -C 8 ) -alkyl-N-heterocyclyl, bis - [(Ci-C 8 ) alkyl] aminoalkyl-N-heterocyclyl, bis - [(Ci-C 8 ) alkyl] aminosulfonyl-N-heterocyclyl, Heteroaryloxyaryl, Heteroaryloxyheteroaryl , Aryloxyheteroaryl, (Ci-C8) alkylsulfinyl, (Ci-C 8) - alkylthio, (Ci-C8) alkylsulfonyl, (C 3 -C 8) cycloalkylsulfinyl, (C 3 -C 8) cycloalkylthio, (C3-C8) cycloalkylsulfonyl, arylsulfinyl, arylthio, arylsulfonyl, amino, (dC 8) - alkylamino, - bis [(Ci-C 8) -alkyl] amino, arylamino, aryl- (Ci-C 8) alkylamino , (C 3 -C 8 ) -cycloalkylamino, formyl, (C 1 -C 8 ) -alkylcarbonyl, arylcarbonyl, imino (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylimino (C 1 -C 8 ) -alkyl , Arylimino- (Ci-C 8) alkyl, (Ci-C8) - alkoxycarbonyl, (C3-C8) -cycloalkoxycarbonyl, (C 3 -C 8) -Cycloa alkyl- (Ci-C8) - alkoxycarbonyl , Aryl- (C 1 -C 8 ) -alkoxycarbonyl, aryl- (C 1 -C 8 ) -alkylaminocarbonyl, Am inocarbonyl, (Ci-C 8) alkylaminocarbonyl, (C 3 -C 8) -Cycloalky aminocarbonyl, bis - [(Ci-C 8) alkyl] aminocarbonyl, N-heterocyclyl-carbonyl, imino, (Ci-C 8 ) - alkylimino, arylimino, (C 3 -C 8) -Cycloalkylimino, (C 3 -C 8) cycloalkyl (Ci-C8) - alkylimino, hydroxyimino, (Ci-C 8) alkoxyimino, (C2-C 8) -Alkenyloxyimino, (C 3 -C 8) -Cycloalkoxyimino, (C 3 -C 8) -Cyloalkyl- (Ci-C 8) alkoxyimino, aryloxyimino, aryl (Ci-C 8) alkoxyimino, heteroaryl ( C 1 -C 8 ) -alkoxyimino, heteroaryloxyimino, heteroarylimino, heterocyclylimino, heterocyclyl (C 1 -C 8 ) -alkylimino,
Aminoimino, (Ci-C8)-Alkylaminoimino, Arylaminoimino, Heteroarylaminoimino, (C3-C8)-Cycloalkylaminoimino, Bis-[(Ci-C8)-Alkyl]aminoimino, Aryl-(Ci-C8)- alkylaminoimino, Aryl[(Ci-C8)-alkyl]aminoimino, (C3-C8)-Cycloalkyl[(Ci-C8)- alkyljaminoimino, (C3-C8)-Cyc!oalkyl-(Ci-C8)-alkylaminoimino, Aminoimino, (Ci-C 8) -Alkylaminoimino, Arylaminoimino, Heteroarylaminoimino, (C 3 -C 8) -Cycloalkylaminoimino, bis - [(Ci-C 8) -alkyl] aminoimino, aryl (Ci-C8) - alkylaminoimino, Aryl [(Ci-C 8 ) -alkyl] aminoimino, (C 3 -C 8 ) -cycloalkyl [(Ci-C 8 ) - alkyl-aminoimino, (C 3 -C 8) -cycloalkyl- (C 1 -C 8) -alkylaminoimino,
Heterocyclylaminoimino, Heteroary!-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, Aryl-(Ci-Ce)- alkoxy-(Ci-C8)-alkyl, Heterocyclyl-N-(Ci-C8)-alkyl, Aryl-[(Ci-C8)-alkyl]amino- (Ci-C8)-alkyl, Ary!-(Ci-C8)-alkyl[(Ci-C8)-aSkyl]amino-(Ci-C8)-alkyl, (Ci-C8)- Alkoxycarbonyl-(Ci-C8)-alkylamino-(Ci-C8)-alkyl, (Ci-CeJ-Alkoxycarbonyl- (Ci-C8)-alkyl[(Ci-C8)-alkyl]amino-(Ci-C8)-alkyl, Heteroaryl-[(Ci-C8)-alkyl]amino- (Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkyl-[(Ci-C8)-alkyl]amino-(Ci-C8)-alkyl, - (C3-C8)-Cycloalkyl-[(Ci-C8)-alkyl]amino-(Ci-C8)-alkyl, (C3-C8)-Cycloalkylamino- (Ci-C8)-alkyl, Aryl-(Ci-C8)-alkoxy-(Ci-C8)-alkylaryl, Heterocyclyl-N-(Ci-C8)- alkylaryl, Ai7l[(Ci-C8)-alkyl]amino-(Ci-C8)-alkylaryl, Aryl-(Ci-C8)-alkyl[(Ci-C8)- alkyl]amino-(Ci-C8)-alkylaryl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkylamino- (Ci-C8)-alkylaryl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl[(Ci-C8)-alkyl]amino- (Ci-C8)-alkylaryl, Heteroaryl[(Ci-C8)-alkyl]amino-(Ci-C8)-alkylaryl, Heteroaryl- (Ci-C8)-alkyl[(Ci-C8)-alkyl]amino-(Ci-C8)-alkylaryl, (C3-C8)-Cycloalkyl[(Ci-C8)- alkyl]amino-(Ci-C8)-alkylaryl, (C3-C8)-Cycloalkylamino-(Ci-C8)-alkylaryl, (Ci-C8)- Alkoxy[(Ci-C8)-alkoxy]-(Ci-C8)-alkylaryl steht, zusätzlich, wenn X für ein Sauerstoffatom oder X für ein Schwefelatom steht, für (Ci-C8)-Haloalkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, (C3-C8)-Halocycloalkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-haloalkyl, Aryl-(Ci-C8)-haloalkyl, (Ci-C8)-Alkylthio- (Ci-C8)-haloalkyl, Bis[(Ci-C8)-alkyl]amino-(Ci-C8)-alkoxy-(Ci-C8)-haloalkyl steht, für Wasserstoff, Hydroxy, (Ci-C8)-Alkyl, (C3-C8)-Cycloalkyl, (C3-C8)- Halocycloalkyl, Halogen, (C2-C8)-Alkenyl-(Ci-C8)-alkyl, (Ci-C8)-Haloalkyl, (C2-C8)-Alkinyl, (C2-C8)-Alkenyl, Cyano-(Ci-C8)-alkyl, Nitro-(Ci-C8)-alkyl, Amino- (Ci-C8)-alkyl, Alkyl-(Ci-C8)-amino-(Ci-C8)-alkyl, Bis-[(Ci-C8)-Alkyl]amino- (Ci-C8)-alkyl, (C2-C8)-Alkinyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)- alkyl, Heterocyclyl-(Ci-C8)-alkyl, (d-CeJ-Alkylcarbonyl, (Ci-C-8)-Alkoxycarbony!, (C3-C8)-Cycloalkoxycarbonyl, (Ci-CsJ-Alkylsulfonyl, Arylsulfonyl, Heterocyclylaminoimino, heteroaryl - (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 6) -alkoxy- (C 1 -C 8 ) -alkyl, heterocyclyl-N- (C 1 -C 8 ) alkyl, aryl - [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkyl [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 4) -alkyl C 8) alkyl, (Ci-C8) - alkoxycarbonyl, (Ci-C8) alkylamino (Ci-C8) alkyl, (Ci-CeJ-alkoxycarbonyl (Ci-C8) alkyl [(Ci-C8 ) -alkyl] amino- (C 1 -C 8 ) -alkyl, heteroaryl - [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl- [ (C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkyl, - (C 3 -C 8 ) -cycloalkyl- [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkyl, (C 3 -C 8) cycloalkylamino- (Ci-C 8) alkyl, aryl (Ci-C8) alkoxy (Ci-C8) alkylaryl, heterocyclyl-N- (Ci-C8) - alkylaryl, Ai7l [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkylaryl, aryl- (C 1 -C 8 ) -alkyl [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkylaryl, ( C 1 -C 8 ) -alkoxycarbonyl- (C 1 -C 8 ) -alkylamino- (C 1 -C 8 ) -alkylaryl, (C 1 -C 8 ) -alkoxycarbonyl- (C 1 -C 8 ) -alkyl [(C 1 -C 8 ) -alkyl] -amino (C 1 -C 8) -alkylaryl, heteroaryl [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkylaryl, heteroaryl- (C 1 -C 8 ) -alkyl [ (C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkylaryl, (C 3 -C 8) -cycloalkyl [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkylaryl, (C 3 -C 8 ) ) -Cycloalkylamino- (C 1 -C 8 ) -alkylaryl, (C 1 -C 8 ) -alkoxy [(C 1 -C 8 ) -alkoxy] - (C 1 -C 8 ) -alkylaryl, in addition when X is an oxygen atom or X represents a sulfur atom, for (Ci-C 8) haloalkyl, (Ci-C 8) alkoxy (Ci-C8) -haloalkyl, (C 3 -C 8) halocycloalkyl, (Ci-C 8) - Haloalkoxy- (C 1 -C 8 ) -haloalkyl, aryl- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -haloalkyl, bis [(C 1 -C 8 ) -alkyl ] amino- (Ci-C8) alkoxy (Ci-C 8) haloalkyl, hydrogen, hydroxy, (Ci-C 8) -alkyl, (C 3 -C 8) -cycloalkyl, (C 3 -C 8) - halocycloalkyl, halogen, (C2-C8) alkenyl (Ci-C 8) alkyl, (Ci-C 8) haloalkyl, (C2-C8) -alkynyl, (C 2 -C 8) Alkenyl, cyano- (C 1 -C 8 ) -alkyl, nitro (C 1 -C 8 ) -alkyl, amino- (C 1 -C 8 ) -alkyl, alkyl- (C 1 -C 8 ) -amino- (C 1 -C 4) -alkyl C 8 ) -alkyl, bis - [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkynyl- (C 1 -C 8 ) -alkyl, aryl- Ci-C 8) alkyl, heteroaryl (Ci-C 8) - alkyl, Heterocyclyl- (C 1 -C 8) -alkyl, (C 1 -C 6 -alkylcarbonyl, (C 1 -C 8) -alkoxycarbonyl, (C 3 -C 8) -cycloalkoxycarbonyl, (C 1 -C 8 -alkylsulfonyl, arylsulfonyl,
Heteroarylsulfonyl, (C3-C-8)-Cyc!oalky!sulfonyl, (Ci-C8)-Alkylsulfinyl, Arylsulfinyl, (C3-C8)-Cycloalkylsulfinyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, Aryl, Heteroaryl, Heterocyclyl, Aminocarbonyi-(Ci-C8)-alkyl, (Ci-C8)-Alkylaminocarbonyl-(Ci-C8)- alkyl, Bis-[(Ci-C8)-alkyl]aminocarbonyl-(Ci-C8)-alkyl, (C3-C8)- Cyc!oalkylaminocarbonyl-(Ci-C8)-alkyl, Hydroxycarbonyl-(Ci-C8)-alkyl, Amino, (Ci-C8)-Alkylamino, Arylamino, (Ci-C8)-Alkoxy sieht und Heteroarylsulfonyl, (C 3 -C 8) -Cyc! Oalky! Sulfonyl, (Ci-C8) alkylsulfinyl, arylsulfinyl, (C 3 -C 8) cycloalkylsulfinyl, (Ci-C8) alkoxycarbonyl (Ci-C 8 ) -alkyl, aryl, heteroaryl, heterocyclyl, aminocarbony- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylaminocarbonyl- (C 1 -C 8 ) -alkyl, bis - [(C 1 -C 8 ) -alkyl] aminocarbonyl - (Ci-C 8) alkyl, (C 3 -C 8) - Cyc! Oalkylaminocarbonyl- (C 1 -C 8) -alkyl, hydroxycarbonyl- (C 1 -C 8 ) -alkyl, amino, (C 1 -C 8 ) -alkylamino, arylamino, (C 1 -C 8 ) -alkoxy and
Z2 für Wasserstoff, (Ci-C8)-Alkyl, (C3-C8)-Cyc!oalkyl, (Ci-C8)-Haloalkyl, (C2-C8)- Alkinyl, (C2-C8)-Alkenyl, Cyano-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkyl, Heteroaryl- (Ci-Cs)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Alkoxycarbonyl steht oder Z 2 is hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) -Cyc Oalkyl, (Ci-C8) -haloalkyl, (C 2 -C 8) - alkynyl, (C 2 -C 8 ) alkenyl, cyano (Ci-C 8 ) alkyl, aryl (Ci-C 8 ) alkyl, heteroaryl (Ci-Cs) alkyl, (Ci-C 8 ) alkylcarbonyl, (Ci-C 8 ) alkoxycarbonyl or
Z1 und Z2 zusammen mit dem Atomen, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome Z 1 and Z 2 together with the atom to which they are attached, a fully saturated or partially saturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden oder  form interrupted and optionally further substituted 5 to 7-membered ring or
Z1 und Z2 zusammen eine N-(Bis-(Ci-C8)-alkyl)sulfanyliden-, N-(Aryl-(d-C8)- alkyl)sulfanyliden-, N-(Bis-(C3-C8)-Cycloalkyl)sulfanyliden-, N-((Ci-C8)-Alkyl-Z 1 and Z 2 together form a N- (bis (Ci-C8) alkyl) sulfanyliden-, N- (aryl (dC 8) - alkyl) sulfanyliden-, N- (bis- (C 3 -C 8 ) -Cycloalkyl) sulfanylidene, N - ((C 1 -C 8 ) -alkyl
(C3-C8)-cycloalkyl)sulfanylidengruppe oder eine N,N-di-(d-C8)- alkylformylidengruppe bilden. (C3-C8) cycloalkyl) sulfanylidengruppe or an N, N-di- (dC 8) - form alkylformylidengruppe.
Besonders bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der allgemeinen Formel (I), worin Particularly preferred is the use according to the invention of compounds of general formula (I) wherein
R1 , R2, R3 unabhängig voneinander für Wasserstoff, lod, Brom, Chlor, Fluor, (C1-C7)- Alkyl, (C3-C/)-Cycloalkyl, (C4-C7)-Cycloalkenyl, (C3-C7)-Halocycloalkyl, (C2-C7)- Alkenyl, (C2-C7)-Alkinyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C )-alkyl, Aryl-(C2-C )-alkenyl, Heteroaryl, Heteroaryl-(Ci-C/)-alkyl, Heterocyclyl, R 1 , R 2 , R 3 independently of one another represent hydrogen, iodine, bromine, chlorine, fluorine, (C 1 -C 7 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, ( C 3 -C 7 ) -halocycloalkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, optionally substituted phenyl, aryl- (C 1 -C 4) -alkyl, aryl- (C 2 -C) -alkenyl , Heteroaryl, heteroaryl (Ci-C /) - alkyl, heterocyclyl,
Heterocyclyl-(Ci-C/)-alkyl, (Ci-C/)-Alkoxy-(Ci-C/)-alkyl, (Ci-C/)-Alkylthio,  Heterocyclyl (Ci-C /) - alkyl, (Ci-C /) - alkoxy (Ci-C /) - alkyl, (Ci-C /) - alkylthio,
(Ci-C )-Haloalkylthio, (Ci-C/)-Haloalkyl, (Ci-C7)-Alkoxy, (d-C/)-Haloalkoxy, (C3-C )-Cycloalkoxy, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxy, Aryloxy, Heteroraryloxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy, (C2-C7)-Alkinyl-(Ci-C7)-alkoxy, (C2-C7)- Alkenyloxy, Bis-[(Ci-C7)-alky!]amino-(Ci-C7)-alkoxy, Tris-[(Ci-C7)-alkyl]silyl, Bis- [(Ci-C )-alkyl]arylsilyl, Bis-[(Ci-C/)-alky!]-(Ci-C/)-alkylsilyl, Tris-[(Ci-C7)- alkyl]silyl-(C2-C7)-alkinyl, Aryl-(C2-C/)-alkinyl, Heteroaryl-(C2-C/)-alkinyl, (C1-C7)- Alkyl-(C2-C/)-alkinyl, (C3-C7)-Cyc!oalkyi-(C2-C7)-aikinyl, (Ci-C7)-Haloalkyl- (C2-C7)-alkinyl, Heterocyclyl-N-(Ci-C7)-a!koxy, Nitro, Cyano, Amino, (C1-C7)-(Ci-C) -haloalkylthio, (Ci-C /) - haloalkyl, (Ci-C 7 ) -alkoxy, (dC /) - haloalkoxy, (C 3 -C) -cycloalkoxy, (C 3 -C 7 ) - cycloalkyl- (Ci-C7) alkoxy, aryloxy, Heteroraryloxy, (Ci-C7) alkoxy (Ci-C7) alkoxy, (C 2 -C 7) alkynyl (Ci-C7) - alkoxy, (C2-C7) - Alkenyloxy, bis - [(Ci-C7) -alky!] Amino- (Ci-C 7 ) -alkoxy, tris - [(Ci-C 7 ) -alkyl] silyl, bis- [(Ci-C) -alkyl] arylsilyl, bis - [(Ci-C /) -alkyl] - (Ci-C /) -alkylsilyl, tris - [(Ci-C 7 ) -alkyl] silyl- (C 2 -C 7 ) -alkynyl, aryl - (C 2 -C 6) alkynyl, heteroaryl- (C 2 -C 6) alkynyl, (C 1 -C 7 ) -alkyl- (C 2 -C 6) alkynyl, (C 3 -C 7 ) -Cyc! oalkyi- (C2-C7) -aikinyl, (Ci-C7) haloalkyl (C 2 -C 7) -alkynyl, heterocyclyl-N- (C 7) -a! koxy, nitro, cyano, amino , (C1-C7) -
Alkylamino, Bis-[(Ci-C7)-aikyi]amino, (Ci-C7)- Aikylcarbonylamino, (C3-C7)- Cycloalkyicarbonylamino, Arylcarbonylamino, (Ci-C )-Aikoxycarbonylamino, Heterocyclyi-(Ci-C7)-alkoxy, (C3-C7)- Cycloalky!-(Ci-C/)-alkyi, (C2-C7)- Haioaikenyl, (C2-C/)-Haloalkinyl, Heterocyciyl-(C2-C/)-alkinyi, (C3-C7)- Halocycloalkoxy, (C2-C/)-Haioaikinyioxy, Arylthio, Heteroaryithio, (Ci-C7)-Alkylamino, bis - [(Ci-C 7 ) -alkyl] amino, (Ci-C 7 ) - Aikylcarbonylamino, (C3-C7) - Cycloalkyicarbonylamino, Arylcarbonylamino, (Ci-C) -Aikoxycarbonylamino, Heterocyclyi- (Ci-C 7 ) -alkoxy, (C 3 -C 7 ) -cycloalkyl-(C 1 -C 4 ) -alkyl, (C 2 -C 7 ) -hioacylic, (C 2 -C 6) -haloalkynyl, heterocyciyl- (C 2 -) C /) alkynyl, (C3-C7) halocycloalkoxy, (C 2 -C) -haloalkylinyloxy, arylthio, heteroaryithio, (C 1 -C 7 )
Alkylsulfinyi, (Ci-C7)-Haloaikylsulfinyi, Arylsuifinyl, Heteroarylsulfinyl, (Ci-C )- Alkyisulfonyl, (Ci-C )-Haloaikyisulfonyl, Aryisulfonyl, Heteroarylsulfonyi, Alkylsulfinyls, (C 1 -C 7 ) -haloalkylsulfinyls, arylsulfinyl, heteroarylsulfinyl, (C 1 -C 4) -alkylsulfonyl, (C 1 -C 4) -haloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyi,
Thiocyanato, Isothiocyanato, (C3-C7)-Cycloa!kylamino, (C3-C/)- Cycloalkyl[(Ci-C7)-alkyl]amino, (C2-C7)-Alkenylamino stehen, ! Thiocyanato, isothiocyanato, (C3-C 7) -Cycloa alkylamino, (C3-C /) - cycloalkyl [(Ci-C 7) alkyl] amino, (C 2 -C 7) alkenylamino stand,
R1 und R2 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden,  form interrupted and optionally further substituted 5 to 7-membered ring,
R2 und R3 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden,  form interrupted and optionally further substituted 5 to 7-membered ring,
W für Sauerstoff, Schwefel steht, W stands for oxygen, sulfur,
X für Sauerstoff, Schwefel, N-R4 steht, R4 für Wasserstoff, (d-C/)-Alkyl, (C3-C7)-Cycloalkyl, (C3-C7)-Cycloalkyl-(Ci-C7)- alkyl, (C4-C7)-Cycloalkenyl, Cyano-(Ci-C/)-alkyl, (C2-C7)-Alkenyl-(Ci-C7)-alkyl, (Ci-C7)-Haloalkyl, (C2-C/)-Alkinyl-(Ci-C )-alkyl, Aryl-(Ci-C )-alkyl, Heteroaryl- (Ci-C/)-alkyl, Heterocyclyl-(Ci-C7)-alkyl, (Ci-C7)-Alkylcarbonyl, (C3-C7)- Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (Ci-C/)-Haloalkylcarbonyl, Heterocyclylcarbonyl, Aryl-(Ci-C7)-alkylcarbonyl, (Ci-CzJ-Alkoxycarbonyl, (C3-C )-Cycloalkyl-(Ci-C/)-alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, X is oxygen, sulfur, NR 4, R 4 is hydrogen, (dC /) - alkyl, (C 3 -C 7) -cycloalkyl, (C 3 -C 7) cycloalkyl (Ci-C7) - alkyl , (C 4 -C 7) cycloalkenyl, cyano (Ci-C /) - alkyl, (C 2 -C 7) alkenyl (Ci-C7) alkyl, (Ci-C7) haloalkyl, (C 2 -C 6) -alkynyl- (C 1 -C 4) -alkyl, aryl- (C 1 -C 4) -alkyl, heteroaryl- (C 1 -C 6) -alkyl, heterocyclyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylcarbonyl, (C 3 -C 7 ) -cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C 1 -C 4) -haloalkylcarbonyl, Heterocyclylcarbonyl, aryl- (Ci-C7) -alkylcarbonyl, (Ci-CzJ-alkoxycarbonyl, (C3-C) -cycloalkyl- (Ci-C /) -alkoxycarbonyl, (C3-C7) -cycloalkoxycarbonyl,
(Ci-C7)-Alkoxycarbonyl-(Ci-C )-alkyl, (Ci-C/)-Alkylsulfonyl, (C3-C7)- Cycloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (C1-C7)- Alkoxycarbonylcarbonyl, Aryl-(Ci-C )-alkoxycarbonylcarbonyl, (C1-C7)- Alkylaminothiocarbonyl, (Ci-C7)-Alkylaminocarbonyl, (C3-C7)- Cycloalkylaminocarbonyl, (Ci-C/)-Alkoxy-(Ci-C7)-alkyl, Bis-[(Ci-C7)- Alkyljaminocarbonyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C7)- Cycloalkoxycarbonyl-(Ci-C )-alkyl steht, für (Ci-C7)-Alkyl, (C2-C/)-Alkenyl, (C3-C7)-Cycloalkyl, (C3-C/)-Cycloalkyl-(Ci-C7)- alkyl, (C4-C7)-Cycloalkenyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C7)- alkyl, Heteroaryl-(Ci-C )-alkyl, Heterocyclyl-(Ci-C7)-alkyl, Heteroaryl, (C 1 -C 7) -alkoxycarbonyl (C 1 -C 4) -alkyl, (C 1 -C 8) -alkylsulfonyl, (C 3 -C 7) -cycloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C 1 -C 7) -alkoxycarbonylcarbonyl, aryl- C) -alkoxycarbonylcarbonyl, (C 1 -C 7) -alkylaminothiocarbonyl, (C 1 -C 7) -alkylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl, (C 1 -C 4) -alkoxy- (C 1 -C 7) -alkyl, bis - [( Ci-C 7 ) - Alkyljaminocarbonyl, aryl, heteroaryl, heterocyclyl, (C3-C7) - Cycloalkoxycarbonyl- (Ci-C) -alkyl, for (Ci-C 7 ) -alkyl, (C 2 -C /) - Alkenyl , (C 3 -C 7) cycloalkyl, (C 3 -C /) - cycloalkyl- (Ci-C7) - alkyl, (C4-C7) cycloalkenyl, optionally substituted phenyl, aryl- (Ci-C7) - alkyl, heteroaryl- (C 1 -C 4) -alkyl, heterocyclyl- (C 1 -C 7) -alkyl, heteroaryl,
Heterocyclyl, Heterocyclylaryl, Heterocyclylheteroaryl, Heteroarylheteroaryl, Heteroarylaryl, Arylaryl, Aryloxyaryl, Aryl-(C2-C7)-alkenyl, Heteroaryl-(C2-C )- alkenyl, Heterocyclyl-(C2-C7)-alkenyl, Aryl-(C2-C/)-alkinyl, Heteroaryl-(C2-C7)- alkinyl, Heterocyclyl-(Ci-C7)-alkinyl, (C3-C/)-Cycloalkyl-(C2-C7)-alkinyl, (C1-C7)- Alkylamino-(Ci-C7)-alkyl, Bis-[(Ci-C )-alkyl]amino-(Ci-C )-alkyl, Hydroxy- (Ci-C )-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Tris-[(Ci-C7)-alkyl]silySoxy-(Ci-C7)- alkyl, Bis-[(Ci-C7)-alkyl]arylsilyloxy-(Ci-C7)-alkyl, Bis-[(Ci-C7)-alkyl]-(Ci-C7)- alkylsilyloxy-(Ci-C/)-alkyl, Bis-[(Ci-C )-alkyl]amino-(Ci-C )-alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkyl, Aryloxy-(Ci-C7)-alkyl, Heterocyclyl, heterocyclylaryl, heterocyclylheteroaryl, heteroarylheteroaryl, heteroarylaryl, arylaryl, aryloxyaryl, aryl- (C 2 -C 7 ) -alkenyl, heteroaryl- (C 2 -C) -alkenyl, heterocyclyl- (C 2 -C 7 ) -alkenyl, aryl- (C 2 -C /) - alkynyl, heteroaryl (C 2 -C 7) - alkynyl, heterocyclyl (Ci-C7) alkynyl, (C 3 -C /) - cycloalkyl- (C 2 -C 7) -alkynyl, ( C1-C7) -alkylamino- (C 1 -C 7 ) -alkyl, bis- [(C 1 -C 4) -alkyl] amino- (C 1 -C 4) -alkyl, hydroxy- (C 1 -C 4) -alkyl, (C 1 -C 4) -alkyl C 7) alkoxy (Ci-C7) alkyl, tris - [(Ci-C 7) alkyl] silySoxy- (Ci-C7) - alkyl, - bis [(Ci-C 7) alkyl] arylsilyloxy- (C 1 -C 7 ) -alkyl, bis - [(C 1 -C 7 ) -alkyl] - (C 1 -C 7 ) -alkylsilyloxy- (C 1 -C 6 ) -alkyl, bis - [(C 1 -C 4) -alkyl] amino- (C 1 -C 4) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (Ci -C 7 ) -alkyl,
Heteroaryloxy-(Ci-C/)-alkyl, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, Arylthio-(CrC/)- alkyl, Heteroarylthio-(Ci-C )-alkyl, (Ci-C7)-Alkoxycarbonyl-N-heterocyclyl, Aryl- (Ci-C7)-alkoxycarbonyl-N-heterocyclyl, (Ci-C7)-Alkyl-N-heterocyclyl, (C1-C7)- Alkylsulfonyl-N-heterocyclyl, Arylsulfonyl-N-heterocyclyl, Heteroarylsulfonyl-N- heterocyclyl, (C3-C7)-Cycloalkylsulfonyl-N-heterocyclyl, (C1-C7)- Haloalkylsulfonyl-N-heterocyclyl, (Ci-C7)-Alkylcarbonyl-N-heterocyclyl, Heteroaryloxy- (Ci-C /) - alkyl, (Ci-C 7 ) -alkylthio (Ci-C 7 ) -alkyl, arylthio (CrC /) - alkyl, heteroarylthio (Ci-C) -alkyl, (Ci -C 7 ) alkoxycarbonyl-N-heterocyclyl, aryl- (C 1 -C 7 ) -alkoxycarbonyl-N-heterocyclyl, (C 1 -C 7 ) -alkyl-N-heterocyclyl, (C 1 -C 7 ) -alkylsulfonyl-N-heterocyclyl, Arylsulfonyl-N-heterocyclyl, heteroarylsulfonyl-N-heterocyclyl, (C 3 -C 7) -cycloalkylsulfonyl-N-heterocyclyl, (C 1 -C 7) -haloalkylsulfonyl-N-heterocyclyl, (C 1 -C 7) -alkylcarbonyl-N-heterocyclyl,
Arylcarbonyl-N-heterocyclyl, Heteroarylcarbonyl-N-heterocyclyl, (C3-C7)- Cycloalkylcarbonyl-N-heterocyclyl, (Ci-C )-Cycloalkyl-N-heterocyclyl, Aryl-N- heterocyclyl, Aryl-(Ci-C7)-alkyl-N-heterocyclyl, Bis-[(Ci-C7)-alkyl]aminoalkyl-N- heterocyclyl, Bis-[(Ci-C7)-alkyl]aminosulfonyl-N-heterocyclyl, Heteroaryloxyaryl, Heteroaryloxyheteroaryl, Aryloxyheteroaryl, (Ci-C/J-Alky!sulfinyl, (C1-C7)- Alkylthio, (Ci-C/)-Alkylsulfonyl, (C3-C/)-Cycloalkylsulfinyl, (C3-C7)-Cycloalkylthio, (C3-C7)-Cyc!oalkylsu!fonyl, Arylsulfinyl, Arylthio, Arylsulfonyl, Amino, (C1-C7)- Alkylamino, Bis-[(Ci-C7)-A!kyl]amino, Arylamino, Aryl-(Ci-C7)-alkylamino,Arylcarbonyl-N-heterocyclyl, heteroarylcarbonyl-N-heterocyclyl, (C3-C7) -cycloalkylcarbonyl-N-heterocyclyl, (Ci-C) -cycloalkyl-N-heterocyclyl, aryl-N-heterocyclyl, aryl- (Ci-C7) - alkyl-N-heterocyclyl, bis - [(Ci-C7) -alkyl] aminoalkyl-N-heterocyclyl, bis - [(Ci-C7) -alkyl] aminosulfonyl-N-heterocyclyl, heteroaryloxyaryl, heteroaryloxyheteroaryl, aryloxyheteroaryl, (Ci-C / J-alkylene sulfinyl, (C1-C7) - alkylthio, (Ci-C /) - alkylsulfonyl, (C 3 -C /) - cycloalkylsulfinyl, (C 3 -C 7) cycloalkylthio, (C 3 -C 7) -cycloalkylsulfonyl, arylsulfinyl, arylthio, arylsulfonyl, amino, (C 1 -C 7) -alkylamino, bis- [(C 1 -C 7) -alkyl] amino, arylamino, aryl- C7) alkylamino,
(C3-C7)-Cycloalkylamino, Formyl, (Ci-C7)-Alkylcarbonyl, Arylcarbonyl, Imino- (Ci-C7)-alkyl, (Ci-C7)-Alkylimino-(Ci-C7)-alkyi, Aryiirnino-(Ci-C7)-alkyl, (C1-C7)- Alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, (C3-C7)-Cycloalkyl-(Ci-C7)- alkoxycarbonyl, Aryl-(Ci-C/)-alkoxycarbonyl, Aryl-(Ci-C/)-alkylaminocarbonyl,(C 3 -C 7 ) -cycloalkylamino, formyl, (C 1 -C 7 ) -alkylcarbonyl, arylcarbonyl, imino (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylimino- (C 1 -C 7 ) -alkyl, aryiirnino ( C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxycarbonyl, (C 3 -C 7 ) -cycloalkoxycarbonyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkoxycarbonyl, aryl- (C 1 -C 4) -alkoxycarbonyl , Aryl (Ci-C /) - alkylaminocarbonyl,
Aminocarbonyl, (d-C/J-Alkylaminocarbonyl, (C3-C7)-Cyc!oalkylaminocarbonyl, Bis-[(Ci-C7)-alkyl]aminocarbonyl, Heterocyclyl-N-carbonyl, Imino, (C1-C7)- Alkylimino, Arylimino, (C3-C7)-Cycloalkylimino, (C3-C7)-Cycloalkyl-(Ci-C-7)- alkylimino, Hydroxyimino, (Ci-C7)-Alkoxyimino, (C2-C7)-A!kenyloxyimino, (C3-C7)-Cycloalkoxyimino, (C3-C7)-Cyloalkyl-(Ci-C7)-a!koxyimino, Aryloxyimino, Aryl-(Ci-C7)-alkoxyimino, Heteroaryl-(Ci-C7)-alkoxyimino, Heteroaryloxyimino, Heteroarylimino, Heterocyclylimino, Heterocyclyl-(Ci-C/)-alkylimino, Aminocarbonyl, (dC / J-alkylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl, bis - [(C 1 -C 7) -alkyl] aminocarbonyl, heterocyclyl-N-carbonyl, imino, (C 1 -C 7) -alkylimino, arylimino, (C3-C7) -cycloalkylimino, (C3-C7) -cycloalkyl- (Ci-C-7) -alkylimino, hydroxyimino, (Ci-C7) -alkoxyimino, (C2-C7) -alkyloxyimino, (C3-C7 ) -Cycloalkoxyimino, (C 3 -C 7) -cycloalkyl- (C 1 -C 7) -alkoxyimino, aryloxyimino, aryl- (C 1 -C 7) -alkoxyimino, heteroaryl- (C 1 -C 7) -alkoxyimino, heteroaryloxyimino, heteroarylimino, heterocyclylimino, heterocyclyl (Ci-C /) - alkylimino,
Aminoimino, (Ci-C7)-Alkylaminoimino, Arylaminoimino, Heteroarylaminoimino, (C3-C7)-Cycloalkylaminoimino, Bis-[(Ci-C7)-Alky!]aminoimino, Aryl-(Ci-C7)- alkylaminoimino, Ary![(Ci-C7)-alkyl]aminoimino, (C3-C7)-Cycloalkyl[(Ci-C7)- alkyljaminoimino, (C3-C7)-Cycloalkyl-(Ci-C7)-alkylaminoimino, Aminoimino, (C 1 -C 7) -alkylaminoimino, arylaminoimino, heteroarylaminoimino, (C 3 -C 7) -cycloalkylaminoimino, bis - [(C 1 -C 7) -alkyl] aminoimino, aryl- (C 1 -C 7) -alkylaminoimino, aryl [( C 1 -C 7) -alkyl] aminoimino, (C 3 -C 7) -cycloalkyl [(C 1 -C 7) -alkyl] aminoimino, (C 3 -C 7) -cycloalkyl- (C 1 -C 7) -alkylaminoimino,
Heterocyciylaminoimino, Heteroaryl-(Ci-C7)-alkoxy-(Ci-C7)-alkyl, Aryl-(Ci-C7)- aikoxy-(Ci-C7)-alkyl, Heterocycly!-N-(Ci-C7)-alkyl, Aryl-[(Ci-C7)-alkyl]amino- (Ci-C7)-aikyi, Aryl-(Ci-C7)-a!kyl[(Ci-C7)-alkyi]amino-(Ci-C7)-aikyl, (C1-C7)- Alkoxycarbonyl-(Ci-C7)-alkylamino-(Ci-C7)-alkyl, (Ci-C7)-Alkoxycarbonyl- (Ci-C7)-alkyl[(Ci-C7)-aikyl]amino-(Ci-C/)-alkyl, Heieroaryl-[(Ci-C7)-alkyl]amino- (Ci-C7)-alkyl, Heteroaryl-(Ci-C7)-alkyi-[(Ci-C7)-a!kyl]amino-(Ci-C7)-alkyi, - (C3-C7)-Cycioalkyl-[(Ci-C7)-alkyl]amino-(Ci-C7)-alkyl, (C3-C7)-Cycloalkylamino- (Ci-C7)-alkyl, Aryl-(Ci-C7)-alkoxy-(Ci-C7)-alkylary!, Heterocyclyi-N-(Ci-C7)- alkylaryl, Aryl[(Ci-C7)-alkyl]amino-(Ci-C7)-alkylaryl, Aryl-(Ci-C7)-aikyl[(Ci-C7)- a!kyl]amino-(Ci-C7)-alkylaryS, (Ci-C/)-Alkoxycarbonyl-(Ci-C7)-alkylamino- (Ci-C7)-alkylary!, (Ci-C7)-Alkoxycarbonyl-(Ci-C7)-alkyl[(Ci-C7)-aikyl]amino- (Ci-C7)-alkylaryi, Heteroaryl[(Ci-C7)-alkyl]amino-(Ci-C7)-alkylaryl, Heteroaryl- (Ci-C7)-alkyl[(Ci-C7)-alkyl]amino-(Ci-C7)-alkylaryl, (C3-C7)-Cycloalky![(Ci-C7)- alkyi]amino-(Ci-C7)-alkylaryl, (C3-C7)-Cycloalkylamino-(Ci-C7)-alkylaryl, (C1-C7)- Aikoxy[(Ci-C7)-alkoxy]-(Ci-C7)-alkylaryl steht, Q zusätzlich, wenn X für ein Sauerstoffatom oder X für ein Schwefelatom steht, für (d-C )-Haloalkyl, (Ci-C/)-Alkoxy-(Ci-C )-haloalkyl, (C3-C/)-Halocycloalkyl, (Ci-C/)-Haloalkoxy-(Ci-C/)-haloalkyl, Aryl-(Ci-C/)-haloalkyl, (Ci-C/)-Alkylthio- (Ci-C/)-haloalkyl, Bis[(Ci-C/)-alkyl]amino-(Ci-C/)-alkoxy-(Ci-C/)-haloalkyl steht, Heterocyciylaminoimino, heteroaryl- (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryl- (C 1 -C 7 ) -acidoxy- (C 1 -C 7 ) -alkyl, heterocyclyl-N- (C 1 -C 7 ) alkyl, aryl - [(C 1 -C 7 ) -alkyl] amino- (C 1 -C 7 ) -alkyl, aryl- (C 1 -C 7 ) -alkyl [(C 1 -C 7 ) -alkyl] -amino ( C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkylamino- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl [(Ci -C7) -acyl] amino- (C 1 -C 6) -alkyl, Heieroaryl - [(C 1 -C 7 ) -alkyl] amino- (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 7 ) -alkyl [(C 1 -C 7 ) -alkyl] amino- (C 1 -C 7 ) -alkyl, - (C 3 -C 7 ) -cycloalkyl- [(C 1 -C 7 ) -alkyl] amino- (C 1 -C 7 ) -alkyl , (C 3 -C 7) cycloalkylamino (Ci-C7) alkyl, aryl (Ci-C7) alkoxy (Ci-C7) -alkylary !, Heterocyclyi-N- (C 7) alkylaryl, aryl [(C 1 -C 7 ) -alkyl] amino- (C 1 -C 7 ) -alkylaryl, aryl- (C 1 -C 7 ) -acyl [(C 1 -C 7 ) -alkyl] amino- (C 1 -C 4 ) -alkyl C 7 ) alkylaryl, (C 1 -C 8) -alkoxycarbonyl- (C 1 -C 7 ) -alkylamino- (C 1 -C 7 ) -alkylaryl, (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl [( C 1 -C 7 ) -alkyl] amino- (C 1 -C 7 ) -alkylaryl, heteroaryl [(C 1 -C 7 ) -alkyl] -amino- (C 1 -C 7 ) -alkylaryl, heteroaryl- (C 1 -C 7 ) -alkyl [(Ci - C7) -alkyl] amino- (C 1 -C 7 ) -alkylaryl, (C 3 -C 7 ) -cycloalky! [(C 1 -C 7 ) -alkyl] amino- (C 1 -C 7 ) -alkylaryl, (C 3 -C 7 ) ) -Cycloalkylamino- (C 1 -C 7 ) -alkylaryl, (C 1 -C 7 ) -acoxy [(C 1 -C 7 ) -alkoxy] - (C 1 -C 7 ) -alkylaryl, In addition, when X is an oxygen atom or X is a sulfur atom, (C 1 -C 6) -haloalkyl, (C 1 -C 6) -alkoxy- (C 1 -C 4) -haloalkyl, (C 3 -C 6) -halocycloalkyl, ( Ci-C /) - haloalkoxy- (Ci-C /) - haloalkyl, aryl- (Ci-C /) - haloalkyl, (Ci-C /) - alkylthio (Ci-C /) - haloalkyl, Bis [(Ci -C () alkyl] amino- (Ci-C /) -alkoxy- (Ci-C /) -haloalkyl,
Z1 für Wasserstoff, Hydroxy, (Ci-C/)-Alkyl, (C3-C7)-Cycloalkyl, (C3-C7)-Z 1 represents hydrogen, hydroxy, (C 1 -C 4 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -
Halocycloalkyl, Brom, Chlor, (C2-C/)-Alkenyl-(Ci-C/)-alkyl, (Ci-C/)-Haloalkyl, (C2-C7)-Alkinyl, (C2-C/)-Alkenyl, Cyano-(Ci-C/)-alkyl, Nitro-(Ci-C/)-alkyl, Amino- (Ci-C/)-alkyl, Alkyl-(Ci-C7)-amino-(Ci-C7)-alkyl, Bis-[(Ci-C )-Alkyl]amino- (Ci-C7)-alkyl, (C2-C7)-Alkinyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkyl, Heteroaryl-(d-C/)- alkyl, Heterocyclyl-(Ci-C/)-alkyl, (Ci-C )-Alkylcarbonyl, (Ci-C7)-Alkoxycarbonyl, (C3-C )-Cycloalkoxycarbonyl, (Ci-C )-Alkylsulfonyl, Arylsulfonyl, Halocycloalkyl, bromine, chlorine, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 7 ) -alkynyl, (C 2 -C / ) Alkenyl, cyano- (Ci-C /) - alkyl, nitro (Ci-C /) - alkyl, amino- (Ci-C /) - alkyl, alkyl- (Ci-C 7 ) -amino- (Ci -C 7) alkyl, - bis [(Ci-C) alkyl] amino- (Ci-C7) alkyl, (C 2 -C 7) alkynyl (Ci-C7) alkyl, aryl (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 4 ) -alkyl, heterocyclyl- (C 1 -C 4) -alkyl, (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 7 ) -alkoxycarbonyl, (C 3 -C 4 ) ) Cycloalkoxycarbonyl, (C 1 -C 4) -alkylsulfonyl, arylsulfonyl,
Heteroarylsulfonyl, (C3-C )-Cycloalkylsulfonyl, (Ci-C/)-Alkylsulfinyl, Arylsulfinyl, (C3-C/)-Cycloalkylsulfinyl, (Ci-C7)-Alkoxycarbonyl-(Ci-C7)-alkyl, Aryl, Heteroaryl, Heterocyclyl, Aminocarbonyl-(Ci-C )-alkyl, (Ci-C7)-Alkylaminocarbonyl-(Ci-C7)- alkyl, Bis-[(Ci-C/)-alkyl]aminocarbonyl-(Ci-C/)-alkyl, (C3-C7)- Cycloalkylaminocarbonyl-(Ci-C/)-alkyl, Hydroxycarbonyl-(Ci-C )-alkyl, Amino, (Ci-C )-Alkylamino, Arylamino, (Ci-C7)-Alkoxy steht und Heteroarylsulfonyl, (C3-C) cycloalkylsulfonyl, (Ci-C /) - alkylsulfinyl, arylsulfinyl, (C 3 -C /) - cycloalkylsulfinyl, (Ci-C 7) alkoxycarbonyl (Ci-C7) alkyl, aryl , heteroaryl, heterocyclyl, aminocarbonyl (Ci-C) alkyl, (Ci-C 7) alkylaminocarbonyl (Ci-C7) - alkyl, - bis [(Ci-C /) - alkyl] aminocarbonyl (Ci C 1 -) alkyl, (C 3 -C 7 ) -cycloalkylaminocarbonyl- (C 1 -C 4 ) -alkyl, hydroxycarbonyl- (C 1 -C 4 ) -alkyl, amino, (C 1 -C 4 ) -alkylamino, arylamino, (C 1 -C 4 ) -alkyl C 7 ) alkoxy and
Z2 für Wasserstoff, (Ci-C7)-Alkyl, (C3-C7)-Cycloalkyl, (Ci-C/)-Haloalkyl, (C2-C7)- Alkinyl, (C2-C/)-Alkenyl, Cyano-(Ci-C/)-alkyl, Aryl-(Ci-C7)-alkyl, Heteroaryl- (Ci-C7)-alkyl, (Ci-C/)-Alkylcarbonyl, (Ci-C7)-Alkoxycarbonyl steht oder Z 2 is hydrogen, (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 7 ) -alkynyl, (C 2 -C /) Alkenyl, cyano- (Ci-C /) - alkyl, aryl- (Ci-C 7 ) -alkyl, heteroaryl- (Ci-C 7 ) -alkyl, (Ci-C /) - alkylcarbonyl, (Ci-C 7 ) Alkoxycarbonyl or
Z1 und Z2 zusammen mit dem Atomen, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome Z 1 and Z 2 together with the atom to which they are attached, a fully saturated or partially saturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden oder Z1 und Z2 zusammen eine N-(Bis-(Ci-C7)-alkyl)su!fanyliden-, N-(Aryl-(Ci-Cz)- alkyl)sulfanyliden-, N-(Bis-(C3-C/)-Cycloalkyl)sulfanyliden-, N-((Ci-C/)-Alkyl- (C3-C/)-cycloalkyl)sulfanylidengruppe oder eine N,N-di-(Ci-C/)- aikylformyiidengruppe bilden. form interrupted and optionally further substituted 5 to 7-membered ring or Z 1 and Z 2 together form an N- (bis (C 1 -C 7) -alkyl) su-fanylidene, N- (aryl- (C 1 -C 6) -alkyl) sulfanylidene, N- (bis- (C 3 - C /) - cycloalkyl) sulfanylidene, N - ((Ci-C /) - alkyl (C3-C /) - cycloalkyl) sulfanylidengruppe or an N, N-di- (Ci-C /) - form aikylformyiidengruppe.
Ganz besonders bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der allgemeinen Formel (I), worin Very particular preference is given to the use according to the invention of compounds of the general formula (I) in which
R\ R2, R3 unabhängig voneinander für Wasserstoff, lod, Brom, Chlor, Fluor, (C1-C4)- Alkyl, (C3-C6)-Cycloalkyl, (C4-C6)-Cycloalkenyl, (C3-C6)-Halocycloalkyl, (C2-C4)- Alkenyl, (C2-C4)-Alkinyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C4)-alkyl, Aryl-(C2-C4)-alkenyl, Heteroaryl, Heteroaryl-(Ci-C4)-alkyl, Heterocyclyl, R 1 , R 3 and R 3 independently of one another represent hydrogen, iodine, bromine, chlorine, fluorine, (C 1 -C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 3 -C 6 ) -halocycloalkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, optionally substituted phenyl, aryl- (C 1 -C 4 ) -alkyl, aryl- (C 2 -C 4 ) -alkenyl, Heteroaryl, heteroaryl- (C 1 -C 4) -alkyl, heterocyclyl,
Heterocyclyl-(Ci-C4)-alkyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio, Heterocyclyl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylthio,
(Ci-C4)-Haloalkylthio, (Ci-C4)-Haloalkyl, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (C3-C6)-Cycloalkoxy, (C3-C6)-Cycloalkyl-(Ci-C4)-alkoxy, Aryloxy, Heteroraryloxy, (Ci-C4)-Alkoxy-(Ci-C4)-alkoxy, (C2-C4)-Alkinyl-(Ci-C4)-alkoxy, (C2-C4)- Alkenyloxy, Bis-[(Ci-C4)-alkyl]amino-(Ci-C4)-alkoxy, Tris-[(Ci-C4)-alkyl]silyl, Bis- [(Ci-C4)-alkyl]arylsilyl, Bis-[(Ci-C4)-alkyl]-(Ci-C4)-alkylsilyl, Tris-[(Ci-C4)- alkyl]silyl-(C2-C4)-alkinyl, Aryl-(C2-C4)-alkinyl, Heteroaryl-(C2-C4)-alkinyl, (C1-C4)- Alkyl-(C2-C4)-alkinyl, (C3-C6)-Cycloalkyl-(C2-C4)-alkinyl, (Ci-C4)-Haloalkyl- (C2-C4)-alkinyl, Heterocyclyl-N-(Ci-C4)-alkoxy, Nitro, Cyano, Amino, (C1-C4)- Alkylamino, Bis-[(Ci-C4)-alkyl]amino, (C1-C4)- Alkylcarbonylamino, (C3-C6)- Cycloalkylcarbonylamino, Arylcarbonylamino, (Ci-C4)-Alkoxycarbonylamino stehen, (C 1 -C 4 ) -haloalkylthio, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 3 -C 6) -cycloalkoxy, (C 3 -C 6) - cycloalkyl (Ci-C4) alkoxy, aryloxy, Heteroraryloxy, (Ci-C 4) alkoxy (Ci-C 4) alkoxy, (C 2 -C 4) alkynyl (Ci-C4) alkoxy, (C 2 -C 4 ) -alkenyloxy, bis- [(C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkoxy, tris - [(C 1 -C 4 ) -alkyl] -silyl, bis- [(C 1 -C 4 ) -alkyl C 4) alkyl] arylsilyl, bis - [(Ci-C 4) alkyl] - (Ci-C 4) alkylsilyl, tris - [(Ci-C4) - alkyl] silyl (C2-C 4) -alkynyl, aryl- (C 2 -C 4 ) -alkynyl, heteroaryl- (C 2 -C 4 ) -alkynyl, (C 1 -C 4 ) -alkyl- (C 2 -C 4 ) -alkynyl, (C 3 -C 6 ) -Cycloalkyl- (C 2 -C 4 ) -alkynyl, (C 1 -C 4 ) -haloalkyl- (C 2 -C 4 ) -alkynyl, heterocyclyl-N- (C 1 -C 4 ) -alkoxy, nitro, cyano, amino, (Cl -C 4) - alkylamino, bis - [(C 1 -C 4 ) -alkyl] amino, (C 1 -C 4 ) -alkylcarbonylamino, (C 3 -C 6) -cycloalkylcarbonylamino, arylcarbonylamino, (C 1 -C 4 ) -alkoxycarbonylamino,
R1 und R2 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden,  form interrupted and optionally further substituted 5 to 7-membered ring,
R2 und R3 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, W für Sauerstoff, Schwefe! sieht, form interrupted and optionally further substituted 5 to 7-membered ring, W for oxygen, sulfur! sees
X für Sauerstoff, Schwefel, N-R4 steht, X is oxygen, sulfur, NR 4 ,
R4 für Wasserstoff, (Ci-C4)-Alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C4)- alkyl, (C4-C6)-Cycloalkenyl, Cyano-(Ci-C4)-alkyl, (C2-C4)-Alkenyl-(Ci-C4)-alkyl, (Ci-C4)-Haloalkyl, (C2-C )-Alkinyl-(Ci-C4)-alkyl, Aryl-(Ci-C4)-alkyS, Heteroaryl- (Ci-C4)-alkyl, Heterocyclyl-(Ci-C )-alkyl, (Ci-C4)-Alkylcarbonyl, (C3-C6)- Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (Ci-C4)-Haloalkylcarbonyl, Heterocyclylcarbonyl, Aryl-(Ci-C4)-alkylcarbonyl, (Ci-C4)-Alkoxycarbonyl, (C3-C6)-Cycloalky!-(Ci-C4)-alkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, (Ci-C4)-Alkoxycarbonyl-(Ci-C )-alkyl, (Ci-C4)-Alkylsulfonyl, (C3-C6)- Cycloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (d-C4)- Alkoxycarbonylcarbonyl, Aryl-(Ci-C4)-alkoxycarbonylcarbonyl, (Ci-C4)- Alkylaminothiocarbonyl, (Ci-C4)-Alkylaminocarbonyl, (C3-C6)- Cycloalkylaminocarbonyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, Bis-[(Ci-C4)- Alky!]aminocarbonyl, Aryl, Heteroaryl, Heterocyclyl, (C3-G3)- Cycloalkoxycarbonyl-(Ci-C4)-alkyl, Heterocyclyl-(Ci-C8)-alkoxy, (C3-C6)- Cycloalkyl-(Ci-C4)-alkyl, (C2-C4)-Haloalkenyl, (C2-C4)-Haloalkinyl, Heterocyclyl- (C2-C )-alkinyl, (C3-C6)-Halocycloalkoxy, (C2-C4)-Haloalkinyloxy, Arylthio, Heteroarylthio, (Ci-C )-Alkylsulfinyl, (Ci-C4)-Haloalkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, (Ci-C4)-Alkylsulfonyl, (Ci-C4)-Haloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, Thiocyanato, Isothiocyanato, (C3-C6)-Cycloalkylamino, (C3-C6)-Cycloalkyl[(Ci-C4)-alkyl]amino, (C2-C4)-Alkenylamino steht, R 4 represents hydrogen, (Ci-C 4) -alkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci-C4) - alkyl, (C 4 -C 6) cycloalkenyl, cyano (Ci-C 4) alkyl, (C2-C4) alkenyl (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 2 -C) alkynyl ( C 1 -C 4 ) -alkyl, aryl- (C 1 -C 4 ) -alkyl, heteroaryl- (C 1 -C 4 ) -alkyl, heterocyclyl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylcarbonyl, ( C 3 -C 6) - cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (Ci-C4) haloalkylcarbonyl, heterocyclylcarbonyl, aryl (Ci-C 4) alkylcarbonyl, (Ci-C 4) alkoxycarbonyl, (C3-C6) - Cycloalky - (Ci-C 4) -alkoxycarbonyl, (C3-C6) cycloalkoxycarbonyl, (Ci-C 4) alkoxycarbonyl (Ci-C) alkyl, (Ci-C 4) alkylsulfonyl, (C 3 - C 6) - cycloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (dC 4) - alkoxycarbonylcarbonyl, aryl (Ci-C 4) -alkoxycarbonylcarbonyl, (Ci-C 4) - alkylaminothiocarbonyl, (Ci-C4) alkylaminocarbonyl, (C3-C6 ) - cycloalkylaminocarbonyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, bis - [(C 1 -C 4 ) -alkyl] aminocarbonyl, aryl, heteroaryl, heterocyclyl, (C 3 -G 3 ) -cycloalkoxycarbonyl- (C 1 -C 4 ) -alkyl, heterocyclyl- (C 1 -C 8) -alkoxy, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4) haloalkynyl, heterocyclyl, (C2-C) alkynyl, (C3-C6) -Halocycloalkoxy, (C2-C 4) -Haloalkinyloxy, arylthio, heteroarylthio, (Ci-C) Alkylsulfinyl, (C 1 -C 4 ) -haloalkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, (C 1 -C 4 ) -alkylsulfonyl, (C 1 -C 4 ) -haloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, thiocyanato, isothiocyanato, (C 3 -C 6) -cycloalkylamino, (C 3 -C 6) -cycloalkyl [(C 1 -C 4 ) -alkyl] amino, (C 2 -C 4 ) -alkenylamino,
Q für (Ci-C )-Alkyl, (C2-C4)-Alkenyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C )- alkyl, (C4-C-6)-Cycloalkenyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C4)- alkyl, Heteroaryl-(Ci-C )-alkyl, Heterocyclyl-(Ci-C4)-alkyl, Heteroaryl, Q is (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -alkenyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 4 -C 6) cycloalkenyl, optionally substituted phenyl, aryl- (Ci-C4) - alkyl, heteroaryl (Ci-C) alkyl, heterocyclyl (Ci-C 4) alkyl, heteroaryl,
Heterocyclyl, Heterocyclylaryl, Heterocyclylheteroaryl, Heteroarylheteroaryl, Heteroarylaryl, Arylaryl, Aryloxyaryl, Aryl-(C2-C4)-alkenyl, Heteroaryl-(C2-C4)- alkenyl, Heterocyclyl-(C2-C4)-alkenyl, Aryl-(C2-C )-alkinyl, Heteroaryl-(C2-C4)- alkinyl, Heterocyclyl-(Ci-C4)-alkinyl, (C3-C6)-Cycloalkyl-(C2-C4)-alkinyl, (C1-C4)- Alkylamino-(Ci-C )-alkyl, Bis-[(Ci-C4)-alkyl]amino-(Ci-C )-alkyl, Hydroxy- (Ci-C4)-alkyl, (Ci-C4)-Alkoxy-(Ci-C4)-a!kyl, Tris-[(Ci-C4)-alkyl]silyloxy-(Ci-C-i)- alkyl, Bis-[(Ci-C4)-alkyl]arylsilyloxy-(Ci-C4)-alkyl, Bis-[(Ci-C4)-alkyl]-(Ci-C4)- alkylsilyloxy-(Ci-C4)-a!kyl, Bis-[(Ci-C4)-alkyl]amino-(Ci-C4)-alkoxy-(Ci-C4)-a!kyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkoxy-(Ci-C4)-alkyl, Aryloxy-(Ci-C4)-alkyl, Heterocyclyl, heterocyclylaryl, heterocyclylheteroaryl, heteroarylheteroaryl, heteroarylaryl, arylaryl, aryloxyaryl, aryl- (C 2 -C 4 ) -alkenyl, heteroaryl- (C 2 -C 4 ) -alkenyl, heterocyclyl- (C 2 -C 4 ) -alkenyl, aryl- C 2 -C) -alkynyl, heteroaryl- (C 2 -C 4 ) -alkynyl, heterocyclyl- (C 1 -C 4 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl- (C 2 -C 4 ) -alkynyl, (Cl -C 4) - alkylamino- (C 1 -C 4 ) -alkyl, bis - [(C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkyl, hydroxyl (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, tris - [(C 1 -C 4 ) -alkyl] silyloxy- (C 1 -C 4 ) -alkyl, bis- [(C 1 -C 4 ) -alkyl] arylsilyloxy- (C 1 -C 4 ) -alkyl, bis - [(C 1 -C 4 ) -alkyl] - (C 1 -C 4 ) -alkylsilyloxy- (C 1 -C 4 ) - alkyl, bis - [(C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, aryloxy- (C 1 -C 4 ) -alkyl,
Heteroaryloxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)-alkyl, Arylthio-(Ci-C4)- alkyl, Heteroarylthio-(Ci-C4)-alkyl, (Ci-C4)-Alkoxycarbonyl-N-heterocyclyl, Aryl- (Ci-C4)-alkoxycarbony!-N-heterocyclyl, (Ci-C4)-Alkyl-N-heterocyclyl, (C1-C4)- Alkylsulfonyl-N-heterocyclyl, Arylsulfonyl-N-heterocyclyl, Heteroarylsulfonyl-N- heterocyclyl, (C3-C6)-Cycloalkylsulfonyl-N-heterocyclyl, (C1-C4)- Haloalkylsulfonyl-N-heterocyclyl, (Ci-C4)-Alkylcarbonyl-N-heterocyclyl, Heteroaryloxy (Ci-C 4) alkyl, (Ci-C4) alkylthio (Ci-C 4) alkyl, arylthio (Ci-C4) - alkyl, heteroarylthio (Ci-C 4) alkyl, (C 1 -C 4 ) -alkoxycarbonyl-N-heterocyclyl, aryl- (C 1 -C 4 ) -alkoxycarbony! -N-heterocyclyl, (C 1 -C 4 ) -alkyl-N-heterocyclyl, (C 1 -C 4 ) -alkylsulfonyl-N- heterocyclyl, arylsulfonyl-N-heterocyclyl, heteroarylsulfonyl-N-heterocyclyl, (C 3 -C 6) -cycloalkylsulfonyl-N-heterocyclyl, (C 1 -C 4) -haloalkylsulfonyl-N-heterocyclyl, (C 1 -C 4) -alkylcarbonyl-N-heterocyclyl,
Arylcarbonyl-N-heterocyclyl, Heteroarylcarbonyl-N-heterocyclyl, (Cß-Ce)- Cycloalkylcarbonyl-N-heterocyclyl, (Ci-CeJ-Cycloalkyl-N-heterocyclyl, Aryl-N- heterocyclyl, Aryl-(Ci-C4)-alkyl-N-heterocyclyl, Bis-[(Ci-C4)-alkyl]aminoalkyl-N- heterocyclyl, Bis-[(Ci-C4)-alkyl]aminosulfonyl-N-heterocyclyl, Heieroaryloxyary!, Heteroaryloxyheteroaryl, Aryloxyheteroaryl, (Ci-C4)-Alkylsulfinyl, (C1-C4)- Alkylthio, (Ci-C4)-Alkylsulfonyl, (C3-C6)-Cycloa!kylsuffinyl, (C3-C6)-Cycloalkylthio, (C3-C6)-Cycloalkylsulfonyl, Arylsulfiny!, Arylthio, Arylsulfonyl, Amino, (C1-C4)- Alkylamino, Bis-[(Ci-C4)-Alkyl]amino, Arylamino, Aryl-(Ci-C4)-alkylamino, (C3-C6)-Cycloalkylamino, Formyl, (Ci-C4)-Alkylcarbonyl, Arylcarbonyl, Imino- (Ci-C )-alkyl, (Ci-C4)-Alkylimino-(Ci-C4)-alkyl, Arylimino-(Ci-C4)-alkyl, (C1-C4)- Alkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, (C3-C6)-Cycloalkyl-(Ci-C4)- alkoxycarbonyl, Ary!-(Ci-C4)-alkoxycarbonyl, Aryl-(Ci-C4)-alkylaminocarbonyl, Aminocarbonyl, (Ci-C4)-Alkylaminocarbonyl, (C3-C6)-Cycloalkylaminocarbonyl, Bis-[(Ci-C4)-alkyl]aminocarbonyl, Heterocyclyl-N-carbonyl, Imino, (C1-C4)- Alkylimino, Arylimino, (C3-C6)-Cycloalkylimino, (C3-C6)-Cycloalkyl-(Ci-C4)- alkylimino, Hydroxyimino, (Ci-C-4)-Alkoxyimino, (C2-C4)-Alkenyloxyimino, (C3-C6)-Cycloalkoxyimino, (C3-C6)-Cyloalkyl-(Ci-C4)-alkoxyimino, Aryloxyimino, Aryl-(Ci-C4)-alkoxyimino, Heteroaryl-(Ci-C4)-alkoxyimino, H eteroa ryl oxy i m i n o , Heteroarylimino, Heterocyclylimino, Heterocyclyl-(Ci-C4)-alkylimino, Arylcarbonyl-N-heterocyclyl, heteroarylcarbonyl-N-heterocyclyl, (C 3 -C 6) -cycloalkylcarbonyl-N-heterocyclyl, (C 1 -C 6 -cycloalkyl-N-heterocyclyl, aryl-N-heterocyclyl, aryl- (C 1 -C 4 ) - Alkyl-N-heterocyclyl, bis - [(Ci-C 4 ) alkyl] aminoalkyl-N-heterocyclyl, bis - [(Ci-C4) alkyl] aminosulfonyl-N-heterocyclyl, Heieroaryloxyary !, Heteroaryloxyheteroaryl, Aryloxyheteroaryl, (Ci -C4) alkylsulfinyl, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylsulfonyl, (C 3 -C 6 ) -cycloalkyl suffinyl, (C 3 -C 6 ) -cycloalkylthio, (C 3 -C 6 ) -cycloalkylsulfonyl , Arylsulfinyl !, arylthio, arylsulfonyl, amino, (C 1 -C 4 ) -alkylamino, bis - [(C 1 -C 4 ) -alkyl] -amino, arylamino, aryl- (C 1 -C 4 ) -alkylamino, (C 3 -C 6) cycloalkylamino, formyl, (Ci-C4) alkylcarbonyl, arylcarbonyl, imino (Ci-C) alkyl, (Ci-C4) -alkylimino (Ci-C 4) alkyl, Arylimino- (Ci-C 4 ) -alkyl, (C 1 -C 4) -alkoxycarbonyl, (C 3 -C 6) -cycloalkoxycarbonyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 4) -alkoxycarbonyl, aryl- (C 1 -C 4) -alkoxycarbonyl, aryl- C 1 -C 4 ) -alkylaminocarbonyl, aminocarbonyl, (C 1 -C 4 ) -alkylamino carbonyl, (C 3 -C 6) -cycloalkylaminocarbonyl, bis - [(C 1 -C 4) -alkyl] aminocarbonyl, heterocyclyl-N-carbonyl, imino, (C 1 -C 4) -alkylimino, arylimino, (C 3 -C 6) -cycloalkylimino, ( C 3 -C 6) -cycloalkyl- (C 1 -C 4) -alkylimino, hydroxyimino, (C 1 -C 4) -alkoxyimino, (C 2 -C 4) -alkenyloxyimino, (C 3 -C 6) -cycloalkoxyimino, (C 3 -C 6) -cycloalkyl - (C 1 -C 4) -alkoxyimino, aryloxyimino, aryl- (C 1 -C 4) -alkoxyimino, heteroaryl- (C 1 -C 4) -alkoxyimino, heteroaryloxy-imino, heteroarylimino, heterocyclylimino, heterocyclyl- (C 1 -C 4) -alkylimino .
Aminoimino, (Ci-C4)-Alkylaminoimino, Aryiaminoimino, Heteroarylaminoimino, (C3-C6)-Cycloalkylaminoimino, Bis-[(Ci-C4)-Alkyl]aminoimino, Aryl-(Ci-C4)- alkylaminoimino, Aryl[(Ci-C4)-alkyl]aminoimino, (C3-C6)-Cycloalkyl[(Ci-C4)- alkyljaminoimino, (C3-C6)-Cycloalkyl-(Ci-C4)-alkylaminoimino, Aminoimino, (C 1 -C 4 ) -alkylaminoimino, aryiaminoimino, heteroarylaminoimino, (C 3 -C 6) -cycloalkylaminoimino, bis - [(C 1 -C 4 ) -alkyl] aminoimino, aryl- (C 1 -C 4 ) -alkylaminoimino, aryl [ (C 1 -C 4 ) -alkyl] aminoimino, (C 3 -C 6) -cycloalkyl [(C 1 -C 4 ) -alkyl] aminoimino, (C 3 -C 6) -cycloalkyl- (C 1 -C 4 ) -alkylaminoimino,
Heterocyclylaminoimino, Heteroaryl-(Ci-C4)-alkoxy-(Ci-C )-alkyl, Aryl-(Ci-C4)- alkoxy-(Ci-C4)-alkyl, Heierocyclyl-N-(Ci-C4)-alkyl! Aryl-[(Ci-C4)-alky!]amino- (Ci-C4)-alkyl, Ary!-(Ci-C4)-aSkyl[(Ci-C4)-alkyl]amino-(Ci-C4)-alkyl! (C1-C4)- Alkoxycarbonyl-(Ci-C4)-alkylamino-(Ci-C4)-alkyl, (Ci-C4)-Alkoxycarbonyl- (Ci-C4)-alkyl[(Ci-C4)-alkyl]amino-(Ci-C4)-alkyl, Heteroaryl-[(Ci-C4)-alkyl]amino- (Ci-C4)-alkyl, Heteroaryl-(Ci-C4)-alkyl-[(Ci-C4)-alkyl]amino-(Ci-C4)-alkyl, (C3-C6)-Cycloalkyl-[(Ci-C4)-alkyl]amino-(Ci-C4)-alkyl, (Cs-CeJ-Cycloalkylamino- (Ci-C4)-alkyl, Aryl-(Ci-C4)-alkoxy-(Ci-C4)-alkylaryl, Heterocyclyl-N-(Ci-C )- alkylaryl, Aryl[(Ci-C4)-alkyl]amino-(Ci-C4)-alkylaryl, Aryl-(Ci-C4)-alkyl[(Ci-C4)- alkyl]amino-(Ci-C4)-alkylaryl, (Ci-C4)-Alkoxycarbonyl-(Ci-C4)-alkylamino- (Ci-C4)-alkylaryl, (Ci-C4)-Alkoxycarbonyl-(Ci-C4)-alkyl[(Ci-C4)-alkyl]amino- (Ci-C4)-alkylaryl, Heteroaryl[(Ci-C4)-alkyl]amino-(Ci-C4)-alkylaryl, Heteroaryl- (Ci-C4)-alkyl[(Ci-C4)-alkyi]amino-(Ci-C4)-alkylaryl, (C3-C6)-Cycloalkyl[(Ci-C4)- alkyl]amino-(Ci-C4)-alkylaryl, (C3-C6)-Cycloalkylamino-(Ci-C4)-alkylaryl, (C1-C4)- Alkoxy[(Ci-C4)-alkoxy]-(Ci-C4)-alky!aryl steht, zusätzlich, wenn X für ein Sauerstoffatom oder X für ein Schwefelatom steht, für (Ci-Cö)-Haloalkyl, (Ci-C4)-Alkoxy-(Ci-C4)-haloalkyl, (C3-C6)-Halocycloalkyl, Heterocyclylaminoimino, heteroaryl- (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, aryl- (C 1 -C 4 ) - alkoxy- (C 1 -C 4 ) -alkyl, heirocyclyl-N- (C 1 -C 4 ) -alkyl ! Aryl - [(C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkyl, aryl- (C 1 -C 4 ) -alkyl [(C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkyl 4 ) -alkyl ! (C 1 -C 4 ) -alkoxycarbonyl- (C 1 -C 4 ) -alkylamino- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxycarbonyl- (C 1 -C 4 ) -alkyl [(C 1 -C 4 ) alkyl] amino- (C 1 -C 4 ) -alkyl, heteroaryl - [(C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkyl, heteroaryl- (C 1 -C 4 ) -alkyl - [( C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkyl, (C 3 -C 6) -cycloalkyl - [(C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkyl, (Cs -CeJ-cycloalkylamino- (C 1 -C 4 ) -alkyl, aryl- (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkylaryl, heterocyclyl-N- (C 1 -C 4 ) -alkylaryl, aryl [(Ci -C 4) alkyl] amino- (Ci-C4) alkylaryl, aryl (Ci-C 4) -alkyl [(Ci-C4) - alkyl] amino- (Ci-C4) alkylaryl, ( C 1 -C 4 -alkoxycarbonyl- (C 1 -C 4 ) -alkylamino- (C 1 -C 4 ) -alkylaryl, (C 1 -C 4 ) -alkoxycarbonyl- (C 1 -C 4 ) -alkyl [(C 1 -C 4 ) - alkyl] amino- (Ci-C 4) -alkyl aryl, heteroaryl, [(Ci-C4) alkyl] amino- (Ci-C4) alkylaryl, heteroaryl (Ci-C4) alkyl [(Ci-C 4 ) -alkyi] amino- (Ci-C4) alkylaryl, (C3-C6) -cycloalkyl [(Ci-C4) - alkyl] amino- (Ci-C4) alkylaryl, (C 3 -C 6) -Cycloalkylamino- (C 1 -C 4 ) -alkylaryl, (C 1 -C 4 ) -alkoxy [(C 1 -C 4 ) -alkoxy] - (C 1 -C 4 ) -alkyl-aryl, in addition, when X is an oxygen atom or X represents a sulfur atom, for (Ci-COE) -haloalkyl, (Ci-C 4) alkoxy (Ci-C 4) -haloalkyl, (C 3 -C 6) halocycloalkyl .
(Ci-C4)-Haloalkoxy-(Ci-C4)-haloalkyl, Aryl-(Ci-C4)-haloalkyl, (Ci-C4)-Alkylthio- (Ci-C4)-haloalkyl, Bis[(Ci-C4)-alkyl]amino-(Ci-C4)-alkoxy-(Ci-C4)-haloalkyl steht, für Wasserstoff, Hydroxy, (Ci-C4)-Alkyl, (C3-C6)-Cycloalkyl, (C3-C6)- Halocycloalkyl, Chlor, (C2-C4)-Alkenyl-(Ci-C4)-alkyl, (Ci-C4)-Haloalkyl, (C2-C4)- Alkinyl, (C2-C4)-Alkenyl, Cyano-(Ci-C4)-alkyl, Nitro-(CrC4)-alkyl, Amino-(Ci-C4)- alkyl, Alkyl-(Ci-C4)-amino-(Ci-C4)-alkyl, Bis-[(Ci-C4)-Alkyl]amino-(Ci-C4)-alkyl, (C2-C4)-Alkinyl-(Ci-C4)-alkyl, Aryl-(Ci-C4)-alkyl, Heteroaryl-(Ci-C4)-alkyl, (C 1 -C 4 ) -haloalkoxy- (C 1 -C 4 ) -haloalkyl, aryl- (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkylthio (C 1 -C 4 ) -haloalkyl, bis [( Ci-C 4) alkyl] amino- (Ci-C 4) alkoxy (Ci-C 4) -haloalkyl, represents hydrogen, hydroxy, (Ci-C 4) -alkyl, (C 3 -C 6) cycloalkyl, (C 3 -C 6) - halocycloalkyl, chlorine, (C2-C4) alkenyl (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C2-C4) - alkynyl, (C 2 -C 4) alkenyl, cyano (Ci-C 4) alkyl, nitro (CrC 4) alkyl, amino (Ci-C4) - alkyl, alkyl (Ci-C 4) - amino- (Ci-C 4) alkyl, - bis [(Ci-C 4) alkyl] amino- (Ci-C 4) alkyl, (C 2 -C 4) alkynyl (Ci-C 4) alkyl, aryl- (C 1 -C 4 ) -alkyl, heteroaryl- (C 1 -C 4 ) -alkyl,
Heterocyclyl-(Ci-C4)-alkyl, (d-C4)-Alkylcarbonyl, (Ci-C4)-Alkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, (Ci-C4)-Alkylsulfonyl, Arylsulfonyl, Heterocyclyl (Ci-C 4) alkyl, (dC 4) alkylcarbonyl, (Ci-C 4) alkoxycarbonyl, (C 3 -C 6) cycloalkoxycarbonyl, (Ci-C 4) alkylsulfonyl, arylsulfonyl,
Heteroarylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, (Ci-C4)-Alkylsulfinyl, Arylsulfinyl, (C3-C6)-Cycloalkylsulfinyl, (Ci-C )-Alkoxycarbonyl-(Ci-C4)-alkyl, Aryl, Heteroaryl, Heterocyclyl, Aminocarbonyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylaminocarbonyl-(Ci-C4)- alkyl, Bis-[(Ci-C4)-alkyl]aminocarbonyl-(Ci-C4)-alkyl, (C3-C6)- Cycloalkylaminocarbonyl-(Ci-C4)-alkyl, Hydroxycarbonyl-(Ci-C4)-alkyl steht Z2 für Wasserstoff, (Ci-C4)-A!kyl, (C3-C6)-Cyc!oalkyl, (Ci-C4)-Haloalkyl, (C2-C4)- Alkinyl, (C2-C4)-Alkenyl, Cyano-(Ci-C4)-alkyl, Aryl-(Ci-C4)-alkyl, Heteroaryl- (Ci-C4)-alkyl, (Ci-C4)-Alkylcarbonyl, (Ci-C4)-Alkoxycarbonyl steht oder Heteroarylsulfonyl, (C 3 -C 6) cycloalkylsulfonyl, (Ci-C 4) alkylsulfinyl, arylsulfinyl, (C3-C 6) cycloalkylsulfinyl, (Ci-C) alkoxycarbonyl (Ci-C 4) alkyl, aryl, heteroaryl, heterocyclyl, aminocarbonyl (Ci-C 4) alkyl, (Ci-C4) alkylaminocarbonyl (Ci-C4) - alkyl, - bis [(Ci-C 4) -alkyl] aminocarbonyl (Ci C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkylaminocarbonyl- (C 1 -C 4 ) -alkyl, hydroxycarbonyl- (C 1 -C 4 ) -alkyl Z 2 is hydrogen, (C 1 -C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 4 ) -alkynyl, (C 2 -C 4 ) -alkenyl, cyano- (C 1 -C 4 ) -alkyl, aryl- (C 1 -C 4 ) -alkyl, heteroaryl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 4 ) -alkyl, C 4 ) alkoxycarbonyl or
Z1 und Z2 zusammen mit dem Atomen, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome Z 1 and Z 2 together with the atom to which they are attached, a fully saturated or partially saturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden oder Z1 und Z2 zusammen eine N-(Bis-(Ci-C-6)-alkyl)sulfanyliden-, N-(Aryl-(Ci-Ce)- alkyl)sulfanyliden-, N-(Bis-(C3-C/)-Cycloalkyl)sulfanyliden-, N-((Ci-C6)-Alkyl- (C3-C/)-cycloalkyl)sulfanylidengruppe oder eine N,N-di-(Ci-Ce)- alkylformylidengruppe bilden. Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten form interrupted and optionally further substituted 5 to 7-membered ring or Z 1 and Z 2 together form an N- (bis (Ci-C-6) alkyl) sulfanyliden-, N- (aryl- (Ci-Ce) - alkyl ) sulfanylidene, N- (bis (C 3 -C 6 ) -cycloalkyl) sulfanylidene, N - ((C 1 -C 6 ) -alkyl- (C 3 -C 5) -cycloalkyl) sulfanylidene group or an N, N- di (Ci-Ce) - alkylformylidengruppe form. The general or preferred ones listed above
Restedefinitionen gelten sowohl für die Endprodukte der Formel (I) als auch Residue definitions apply both to the end products of the formula (I) and
entsprechend für die jeweils zur Herstellung benötigten Ausgangs- oder accordingly for each required for the production starting or
Zwischenprodukte. Diese Restedefinitionen können untereinander, also auch zwischen den angegebenen bevorzugten Bereichen beliebig kombiniert werden. Intermediates. These remainder definitions can be combined with one another as desired, ie also between the specified preferred ranges.
Im Wesentlichen sind die zuvor genannten Haloalkyl-substituierten 2- Amidobenzoxazole und 2-Amidobenzothiazole der allgemeinen Formel (I) ebenfalls noch nicht im Stand der Technik bekannt. Somit gelten als weiterer Teil der Erfindung Haloalkyl-substituierte 2 -Amidobenzoxazole und 2-Amidobenzothiazole der In essence, the aforementioned haloalkyl-substituted 2-amidobenzoxazoles and 2-amidobenzothiazoles of the general formula (I) are likewise not yet known in the prior art. Thus, as a further part of the invention haloalkyl substituted 2 -Amidobenzoxazole and 2-amidobenzothiazoles of
allgemeinen Formel (I) oder deren Salze, general formula (I) or salts thereof,
R\ R2, R3 unabhängig voneinander für Wasserstoff, Halogen, (Ci-CeJ-Alkyl, (C3-C-8)- Cycloalkyl, (C4-C8)-Cycloalkenyl, (C3-C8)-Halocycloalkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C-8)-alkyl, Aryl- (C2-C8)-alkenyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl- (Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio, (Ci-C8)- Haloalkylthio, (Ci-C8)-Haloalkyl, (Ci-C8)-Alkoxy, (Ci-C8)-Haloalkoxy, (C3-C8)- Cycloalkoxy, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxy, Aryloxy, Heteroraryloxy, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy, (C2-C8)-Alkinyl-(Ci-C8)-alkoxy, (C2-C8)- Alkenyloxy, Bis-[(Ci-C8)-alkyl]amino-(Ci-C8)-alkoxy, Tris-[(Ci-C8)-alkyl]silyl, Bis- [(Ci-C8)-alkyl]arylsilyl, Bis-[(Ci-C8)-alkyl]-(Ci-C8)-alkylsilyl, Tris-[(Ci-C8)- alkyl]silyl-(C2-C8)-alkinyl, Aryl-(C2-C8)-alkinyl, Heteroaryl-(C2-C8)-alkinyl, (Ci-C8)- Alkyl-(C2-C8)-alkinyl, (C3-C8)-Cycloalkyl-(C2-C8)-alkinyl, (Ci-Ce)-Haloalkyl- (C2-C8)-alkinyl, Heterocyclyl-N-(Ci-Cs)-alkoxy, Nitro, Cyano, Amino, (Ci-Ce)- Alkylamino, Bis-[(Ci-C8)-alkyl]amino, (Ci-Cs)- Alkylcarbonylamino, (C3-C8)- Cycloalkylcarbonylamino, Arylcarbonylamino, (Ci-CsJ-Alkoxycarbonylamino, Heterocyclyl-(Ci-C8)-alkoxy, (C3-C8)- Cycloalkyl-(Ci-C8)-alkyl, (C2-C8)- Haloalkenyl, (C2-C8)-Haloalkinyl, Heterocyclyl-(C2-C8)-alkinyl, (C3-C8)- Halocycloalkoxy, (C2-C8)-Haloalkinyloxy, Arylthio, Heteroarylthio, (Ci-Ce)- Alkylsulfinyl, (d-CeJ-Haloalkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, (Ci-Cs)- Alkylsulfonyl, (Ci-Ce)-Haloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, R \ R 2 , R 3 independently of one another represent hydrogen, halogen, (C 1 -C 6 -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C 3 -C 8 ) -halocycloalkyl , (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, optionally substituted phenyl, aryl- (C 1 -C 8 ) -alkyl, aryl- (C 2 -C 8 ) -alkenyl, heteroaryl, heteroaryl- C 1 -C 8 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio, C 8) - haloalkylthio, (Ci-C 8) haloalkyl, (Ci-C 8) alkoxy, (Ci-C8) -haloalkoxy, (C 3 -C 8) - cycloalkoxy, (C3-C8) cycloalkyl - (C 1 -C 8 ) -alkoxy, aryloxy, heteroaryloxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy, (C 2 -C 8 ) -alkynyl- (C 1 -C 8 ) -alkoxy, (C 2 -C 8) - alkenyloxy, - bis [(Ci-C 8) alkyl] amino- (Ci-C8) alkoxy, tris - [(Ci-C 8) alkyl] silyl, bis [(Ci- C 8) alkyl] arylsilyl, bis - [(Ci-C 8) alkyl] - (Ci-C8) alkylsilyl, tris - [(Ci-C 8) - alkyl] silyl (C2-C8) alkynyl, aryl (C2-C8) alkynyl, heteroaryl (C 2 -C 8) -alkynyl, (Ci-C 8) - alkyl (C2-C8) -alkynyl, (C 3 -C 8) cycloalkyl (C2-C8) - alkynyl, (C 1 -C 6) -haloalkyl- (C 2 -C 8) -alkynyl, heterocyclyl-N- (C 1 -C 8) -alkoxy, nitro, cyano, amino, (C 1 -C 6) -alkylamino, bis - [(Ci -C8) -alkyl] amino, (Ci-Cs) - alkylcarbonylamino, (C3-C8) - cycloalkylcarbonylamino, arylcarbonylamino, (Ci-CsJ-alkoxycarbonylamino, heterocyclyl (Ci-C 8 ) -alkoxy, (C 3 -C 8 ) - cycloalkyl- (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, heterocyclyl- (C 2 -C 8 ) -alkynyl, (C 3 -C 8 ) - halocycloalkoxy, (C 2 -C 8) -haloalkynyloxy, arylthio, heteroarylthio, (C 1 -C 6) -alkylsulfinyl, (d-CeJ-haloalkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, (C 1 -C 8) -alkylsulfonyl, (Ci-Ce) Haloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl,
Thiocyanato, Isothiocyanato, (C3-C8)-Cycloalkylamino, (C3-C8)- Cycloalkyl[(Ci-C8)-alkyl]amino, (C2-C8)-Alkenylamino stehen, Thiocyanato, isothiocyanato, (C 3 -C 8) -cycloalkylamino, (C 3 -C 8) -cycloalkyl [(C 1 -C 8) -alkyl] amino, (C 2 -C 8) -alkenylamino,
R1 und R2 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, R2 und R3 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome R 1 and R 2 with the atoms to which they are attached form a completely saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring, R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden,  form interrupted and optionally further substituted 5 to 7-membered ring,
W für Sauerstoff, Schwefel steht, X für Sauerstoff, Schwefel steht, W is oxygen, sulfur, X is oxygen, sulfur is,
Q für (Ci-C8)-Haloalkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, (C3-C8)-Halocycloalkyl, (Ci-C8)-Haloalkoxy-(d-C8)-haloalkyl, Aryl-(Ci-C8)-haloalkyl, (Ci-C8)-Alkylthio- (Ci-C8)-haloalkyl, Bis[(Ci-C8)-alkyl]amino-(Ci-C8)-alkoxy-(Ci-C8)-haloalkyl steht, Q is (Ci-C 8) haloalkyl, (Ci-C 8) alkoxy (Ci-C8) -haloalkyl, (C 3 -C 8) halocycloalkyl, (Ci-C8) haloalkoxy (dC 8 ) -haloalkyl, aryl- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -haloalkyl, bis [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 4) -alkyl C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl,
Z1 für Wasserstoff, Hydroxy, (Ci-Cs)-Alkyl, (C3-C8)-Cycloalkyl, (C3-C8)-Z 1 is hydrogen, hydroxy, (C 1 -C 5 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -
Halocycloalkyl, Halogen, (C2-C8)-Alkenyl-(Ci-C8)-alkyl, (Ci-C8)-Haloalkyl, (C2-C8)-Alkinyl, (C2-C8)-Alkenyl, Cyano-(Ci-C8)-alkyl, Nitro-(Ci-C8)-alkyl, Amino- (Ci-C8)-alkyl, Alkyl-(Ci-C8)-amino-(Ci-C8)-alkyl, Bis-[(Ci-C8)-Alkyl]amino- (Ci-C8)-alkyl, (C2-C8)-Alkinyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkyl, Heteroaryl-(Ci-Cs)- alkyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-Cs)-Alkylcarbonyl, (Ci-Cs)-Alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (Ci-C8)-Alkylsulfonyl, Arylsulfonyl, Halocycloalkyl, halogen, (C 2 -C 8) alkenyl (Ci-C 8) alkyl, (Ci-C 8) haloalkyl, (C 2 -C 8) -alkynyl, (C 2 -C 8) - Alkenyl, cyano- (C 1 -C 8 ) -alkyl, nitro (C 1 -C 8 ) -alkyl, amino- (C 1 -C 8 ) -alkyl, alkyl- (C 1 -C 8 ) -amino- (Ci-C 8) -alkyl, - bis [(Ci-C 8) alkyl] amino- (Ci-C 8) alkyl, (C 2 -C 8) alkynyl (Ci-C 8) alkyl, aryl ( Ci-C 8) alkyl, heteroaryl (Ci-Cs) - alkyl, heterocyclyl- (Ci-C 8) alkyl, (Ci-Cs) alkylcarbonyl, (Ci-Cs) -alkoxycarbonyl, (C3-C 8 ) Cycloalkoxycarbonyl, (C 1 -C 8 ) -alkylsulfonyl, arylsulfonyl,
Heteroarylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, (Ci-C8)-Alkylsulfinyl, Arylsulfinyl, (C3-C8)-Cycloalkylsulfinyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, Aryl, Heteroaryl, Heterocyclyl, Aminocarbonyl-(CrC8)-alkyl, (Ci-C8)-Alkylaminocarbonyl-(Ci-C8)- alkyl, Bis-[(Ci-C8)-alkyl]aminocarbonyl-(Ci-C8)-alkyl, (C3-C8)- Cycloalkylaminocarbonyl-(Ci-C8)-alkyl, Hydroxycarbonyl-(Ci-C8)-alkyl, Amino, (Ci-C8)-Alkylamino, Arylamino, (d-C8)-Alkoxy steht und Heteroarylsulfonyl, (C 3 -C 8 ) -cycloalkylsulfonyl, (C 1 -C 8 ) -alkylsulfinyl, arylsulfinyl, (C 3 -C 8 ) -cycloalkylsulfinyl, (C 1 -C 8 ) -alkoxycarbonyl- (C 1 -C 8 ) -alkyl, aryl , heteroaryl, heterocyclyl, aminocarbonyl (-C 8) alkyl, (Ci-C8) alkylaminocarbonyl (Ci-C8) - alkyl, - bis [(Ci-C 8) alkyl] aminocarbonyl (Ci-C 8) -alkyl, (C 3 -C 8) - cycloalkylaminocarbonyl (Ci-C 8) alkyl, hydroxycarbonyl- (Ci-C 8) alkyl, amino, (Ci-C 8) alkylamino, arylamino, (dC 8 ) alkoxy and
Z2 für Wasserstoff, (d-C8)-Alkyl, (C3-C8)-Cycloalkyl, (d-C8)-Haloalkyl, (C2-C8)- Alkinyl, (C2-C8)-Alkenyl, Cyano-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkyl, Heteroaryl- (Ci-Cs)-alkyl, (d-C8)-Alkylcarbonyl, (Ci-C8)-Alkoxycarbonyl steht oder Z 2 is hydrogen, (DC 8) alkyl, (C 3 -C 8) cycloalkyl, (DC 8) -haloalkyl, (C 2 -C 8) - alkynyl, (C 2 -C 8) alkenyl, cyano - (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, (C 1 -C 8 ) -alkoxycarbonyl or
Z1 und Z2 zusammen mit dem Atomen, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome Z 1 and Z 2 together with the atom to which they are attached, a fully saturated or partially saturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden oder Z1 und Z2 zusammen eine N-(Bis-(Ci-C6)-alkyl)sulfanyliden-, N-(Aryl-(Ci-Ce)- alkyl)sulfanyliden-, N-(Bis-(C3-C/)-Cycloalkyl)sulfanyliden-, N-((Ci-C6)-Alkyl- (C3-C/)-cycloalkyl)sulfanylidengruppe oder eine N,N-di-(Ci-Ce)- alkylformylidengruppe bilden. Bevorzugt sind erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin form interrupted and optionally further substituted 5 to 7-membered ring or Z 1 and Z 2 together form a N- (bis (Ci-C6) alkyl) sulfanyliden-, N- (aryl- (Ci-Ce) - alkyl) sulfanyliden , N- (bis (C 3 -C 6 ) -cycloalkyl) sulfanylidene, N - ((C 1 -C 6 ) -alkyl- (C 3 -C 5) -cycloalkyl) sulfanylidene group or an N, N-di- (Ci-Ce) - alkylformylidengruppe form. Preference is given to compounds of the general formula (I) according to the invention, in which
R\ R2, R3 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C4)-Alkyl, (C3-C8)- Cycloalkyl, (C4-C8)-Cycloalkenyl, (C3-C8)-Halocycloalkyl, (C2-C4)-Alkenyl, R \ R 2, R 3 are independently hydrogen, halogen, (Ci-C 4) -alkyl, (C 3 -C 8) - cycloalkyl, (C 4 -C 8) cycloalkenyl, (C 3 -C 8) -Halocycloalkyl, (C 2 -C 4 ) -alkenyl,
(C2-C4)-Alkinyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C4)-alkyl, Aryl- (C2-C )-alkenyl, Heteroaryl, Heteroaryl-(Ci-C4)-alkyl, Heterocyclyl, Heterocyclyl-(C 2 -C 4 ) -alkynyl, optionally substituted phenyl, aryl- (C 1 -C 4 ) -alkyl, aryl- (C 2 -C 5) -alkenyl, heteroaryl, heteroaryl- (C 1 -C 4 ) -alkyl, heterocyclyl, heterocyclyl -
(Ci-C4)-alkyl, (Ci-C4)-Alkoxy-(Ci-C )-alkyl, (C1-C4)-Alkylthio, (C1-C4)- Haloalkylthio, (d-C4)-Haloalkyl, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (C3-C8)- Cycloalkoxy, (C3-C8)-Cycloalkyl-(Ci-C4)-alkoxy, Aryloxy, Heteroraryloxy, (Ci-C 4) alkyl, (Ci-C 4) alkoxy (Ci-C) alkyl, (C 1 -C 4) alkylthio, (C1-C4) - haloalkylthio, (dC 4) -haloalkyl , (Ci-C 4) alkoxy, (Ci-C 4) -haloalkoxy, (C 3 -C 8) - cycloalkoxy, (C3-C8) -cycloalkyl- (Ci-C4) alkoxy, aryloxy, Heteroraryloxy,
(Ci-C4)-Alkoxy-(Ci-C4)-alkoxy, (C2-C4)-Alkinyl-(Ci-C4)-alkoxy, (C2-C4)- Alkenyloxy, Bis-[(Ci-C4)-alkyl]amino-(Ci-C4)-alkoxy, Tris-[(Ci-C )-alkyl]silyl, Bis-(Ci-C 4) alkoxy (Ci-C 4) alkoxy, (C 2 -C 4) alkynyl (Ci-C 4) alkoxy, (C 2 -C 4) - alkenyloxy, bis [ (C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkoxy, tris - [(C 1 -C 4) -alkyl] -silyl, bis-
[(Ci-C4)-alkyl]arylsilyl, Bis-[(Ci-C4)-alkyl]-(Ci-C4)-alkylsilyl, Tris-[(Ci-C4)- alkyl]silyl-(C2-C4)-alkinyl, Aryl-(C2-C4)-alkinyl, Heteroaryl-(C2-C4)-alkinyl, (Ci-C )- Alkyl-(C2-C4)-alkinyl, (C3-C8)-Cycloalkyl-(C2-C4)-alkinyl, (Ci-C4)-Haloalkyl- (C2-C4)-alkinyl, Heterocyclyl-N-(Ci-C4)-alkoxy, Nitro, Cyano, Amino, (Ci-C4)- Alkylamino, Bis-[(Ci-C )-alkyl]amino, (Ci-C )- Alkylcarbonylamino, (C3-C8)-[(Ci-C 4) alkyl] arylsilyl, bis - [(Ci-C 4) alkyl] - (Ci-C 4) alkylsilyl, tris - (silyl- C - [alkyl (Ci-C 4)] 2 -C 4) -alkynyl, aryl (C 2 -C 4) alkynyl, heteroaryl (C 2 -C 4) -alkynyl, (Ci-C) - alkyl (C 2 -C 4) -alkynyl, (C 3 -C 8) cycloalkyl (C 2 -C 4) -alkynyl, (Ci-C 4) haloalkyl (C 2 -C 4) -alkynyl, heterocyclyl-N- (Ci-C4) - alkoxy, nitro, cyano, amino, (Ci-C4) - alkylamino, - bis [(Ci-C) alkyl] amino, (Ci-C) - alkylcarbonylamino, (C3-C8) -
Cycloalkylcarbonylamino, Arylcarbonylamino, (Ci-C4)-Alkoxycarbonylamino, Heterocyclyl-(Ci-C4)-alkoxy, (C3-C8)- Cycloalkyl-(Ci-C4)-alkyl, (C2-C4)- Haloalkenyl, (C2-C4)-Haloalkinyl, Heterocyclyl-(C2-C4)-alkinyl, (C3-C8)- Halocycloalkoxy, (C2-C4)-Haloalkinyloxy, Arylthio, Heteroarylthio, (Ci-C4)- Alkylsulfinyl, (Ci-C4)-Haloalkylsu!finyl, Arylsu!finyl, Heteroarylsu!finyl, (C1-C4)- Alkylsulfonyl, (Ci-C4)-Haloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, Cycloalkylcarbonylamino, arylcarbonylamino, (Ci-C 4) alkoxycarbonylamino, heterocyclyl (Ci-C 4) alkoxy, (C 3 -C 8) - cycloalkyl, (Ci-C 4) alkyl, (C 2 -C 4) Haloalkenyl, (C 2 -C 4 ) -haloalkynyl, heterocyclyl- (C 2 -C 4 ) -alkynyl, (C 3 -C 8 ) -halocycloalkoxy, (C 2 -C 4 ) -haloalkynyloxy, arylthio, heteroarylthio, ( Ci-C 4 ) - Alkylsulfinyl, (C 1 -C 4) -haloalkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, (C 1 -C 4) -alkylsulfonyl, (C 1 -C 4) -haloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl,
Thiocyanato, Isothiocyanato, (C3-C8)-Cycloalkylamino, (C3-C8)- Cycloalkyl[(Ci-C4)-alkyl]amino, (C2-C4)-Alkenylamino stehen, Thiocyanato, isothiocyanato, (C 3 -C 8) -cycloalkylamino, (C 3 -C 8) -cycloalkyl [(C 1 -C 4 ) -alkyl] amino, (C 2 -C 4 ) -alkenylamino,
R1 und R2 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden,  form interrupted and optionally further substituted 5 to 7-membered ring,
R2 und R3 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden,  form interrupted and optionally further substituted 5 to 7-membered ring,
W für Sauerstoff, Schwefel steht, X für Sauerstoff, Schwefel steht, Q für (Ci-C/)-Haloalkyl, (Ci-C4)-Alkoxy-(Ci-C4)-haloalkyl, (C3-C8)-Halocycloalkyl,W is oxygen, sulfur, X is oxygen, sulfur, Q is (Ci-C /) - haloalkyl, (Ci-C 4) alkoxy (Ci-C 4) -haloalkyl, (C 3 -C 8) halocycloalkyl,
(Ci-C4)-Haloalkoxy-(Ci-C4)-haloalkyl, Aryl-(Ci-C4)-haloalkyl, (Ci-C4)-Alkylthio- (Ci-C4)-haloalkyl, Bis[(Ci-C4)-alkyl]amino-(Ci-C4)-alkoxy-(Ci-C4)-haloalkyl steht, (C 1 -C 4 ) -haloalkoxy- (C 1 -C 4 ) -haloalkyl, aryl- (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkylthio (C 1 -C 4 ) -haloalkyl, bis [( C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -haloalkyl,
Z1 für Wasserstoff, Hydroxy, (Ci-C4)-Alkyl, (C3-C8)-Cycloalkyl, (C3-C8)- Halocycloalkyl, Halogen, (C2-C4)-Alkenyl-(Ci-C4)-alkyl, (Ci-C4)-Haloalkyl, Z 1 represents hydrogen, hydroxy, (Ci-C 4) -alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) - halocycloalkyl, halogen, (C2-C4) alkenyl (Ci C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl,
(C2-C4)-Alkinyl, (C2-C4)-Alkenyl, Cyano-(Ci-C4)-alkyl, Nitro-(Ci-C4)-alkyl, Amino- (Ci-C4)-alkyl, Alkyl-(Ci-C4)-amino-(Ci-C4)-alkyl, Bis-[(Ci-C4)-Alkyl]amino- (Ci-C4)-alkyl, (C2-C4)-Alkinyl-(Ci-C4)-alkyl, Aryl-(Ci-C4)-alkyl, Heteroaryl-(Ci-C4)- alkyl, Heterocyclyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylcarbonyl, (Ci-C4)-Alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (Ci-C4)-Alkylsulfonyl, Arylsulfonyl, (C 2 -C 4 ) -alkynyl, (C 2 -C 4 ) -alkenyl, cyano- (C 1 -C 4 ) -alkyl, nitro- (C 1 -C 4 ) -alkyl, amino- (C 1 -C 4 ) -alkyl , alkyl (Ci-C 4) amino (Ci-C 4) alkyl, - bis [(Ci-C 4) alkyl] amino- (Ci-C 4) alkyl, (C 2 -C 4 ) alkynyl (Ci-C4) alkyl, aryl (Ci-C 4) -alkyl, heteroaryl- (Ci-C4) - alkyl, heterocyclyl- (Ci-C 4) alkyl, (Ci-C 4 ) -Alkylcarbonyl, (C 1 -C 4 ) -alkoxycarbonyl, (C 3 -C 8) -cycloalkoxycarbonyl, (C 1 -C 4 ) -alkylsulfonyl, arylsulfonyl,
Heteroarylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, (Ci-C4)-Alkylsulfinyl, Arylsulfinyl, (C3-C8)-Cycloalkylsulfinyl, (Ci-C4)-Alkoxycarbonyl-(Ci-C4)-alkyl, Aryl, Heteroaryl, Heterocyclyl, Aminocarbonyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylaminocarbonyl-(Ci-C4)- alkyl, Bis-[(Ci-C4)-alkyl]aminocarbonyl-(Ci-C4)-alkyl, (C3-C8)- Cyc!oalkylaminocarbonyl-(Ci-C4)-alkyl, Hydroxycarbonyl-(Ci-C4)-alkyl, Amino, (Ci-C4)-Alkylamino, Arylamino, (Ci-C4)-Alkoxy sieht und Heteroarylsulfonyl, (C 3 -C 6) -cycloalkylsulfonyl, (C 1 -C 4 ) -alkylsulfinyl, arylsulfinyl, (C 3 -C 8) -cycloalkylsulfinyl, (C 1 -C 4 ) -alkoxycarbonyl- (C 1 -C 4 ) -alkyl, aryl, heteroaryl , heterocyclyl, aminocarbonyl (Ci-C 4) alkyl, (Ci-C4) alkylaminocarbonyl (Ci-C4) - alkyl, - bis [(Ci-C 4) -alkyl] aminocarbonyl (Ci-C 4 ) -alkyl, (C 3 -C 8 ) - Cyc! Oalkylaminocarbonyl- (C 1 -C 4) -alkyl, hydroxycarbonyl- (C 1 -C 4) -alkyl, amino, (C 1 -C 4) -alkylamino, arylamino, (C 1 -C 4) -alkoxy and
Z2 für Wasserstoff, (Ci-C4)-Alkyl, (C3-C8)-Cyc!oalkyl, (Ci-C4)-Haloalkyl, (C2-C4)- Alkinyl, (C2-C4)-Alkenyl, Cyano-(Ci-C4)-alkyl, Aryl-(Ci-C4)-alkyl, Heteroaryl- (Ci-C4)-alkyl, (Ci-C4)-Alkylcarbonyl, (Ci-C4)-Alkoxycarbonyl steht oder Z 2 is hydrogen, (Ci-C 4) -alkyl, (C 3 -C 8) -Cyc Oalkyl, (Ci-C 4) -haloalkyl, (C2-C4) - alkynyl, (C2-C4) - Alkenyl, cyano- (C 1 -C 4 ) -alkyl, aryl- (C 1 -C 4 ) -alkyl, heteroaryl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 4 ) Alkoxycarbonyl or
Z1 und Z2 zusammen mit dem Atomen, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome Z 1 and Z 2 together with the atom to which they are attached, a fully saturated or partially saturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden oder  form interrupted and optionally further substituted 5 to 7-membered ring or
Z1 und Z2 zusammen eine N-(Bis-(Ci-C6)-alkyl)sulfanyliden-, N-(Aryl-(Ci-Ce)- alkyl)sulfanyliden-, N-(Bis-(C3-C7)-Cycloalkyl)sulfanyliden-, N-((Ci-C6)-Alkyl-Z 1 and Z 2 together form a N- (bis (C 1 -C 6 ) alkyl) sulfanylidene, N- (aryl- (C 1 -C 6 ) -alkyl) sulfanylidene, N- (bis (C 3 -C 7 ) -Cycloalkyl) sulfanylidene, N - ((C 1 -C 6 ) -alkyl-
(C3-C )-cycloalkyl)sulfanylidengruppe oder eine N, N-di-(Ci-Ce)- alkylformylidengruppe bilden. (C3-C) -cycloalkyl) sulfanylidengruppe or an N, N-di (Ci-Ce) - alkylformylidengruppe.
Im Wesentlichen sind die zuvor genannten Sulfanyliden-substituierten 2- Amidobenzimidazole der allgemeinen Formel (I) ebenfalls noch nicht im Stand derEssentially, the abovementioned sulfanylidene-substituted 2-amidobenzimidazoles of the general formula (I) are also not yet in the state of the art
Technik bekannt. Somit gelten als weiterer Teil der Erfindung Sulfanyliden-substituierte 2 -Amidobenzimidazole der allgemeinen Formel (I) oder deren Salze, Technique known. Thus, sulfanylidene-substituted 2-amidobenzimidazoles of the general formula (I) or salts thereof are considered as a further part of the invention,
worin , R2, R3 unabhängig voneinander für Wasserstoff, Halogen, (Ci-CeJ-Alkyl, (C3-C-8)- Cycloalkyl, (C4-C8)-Cycloalkenyl, (C3-C8)-HalocycSoalkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C8)-alkyl, Aryl- (C2-C8)-alkenyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl- (Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (CrC8)-Alkylthio, (Ci-C8)- Haloalkylthio, (Ci-C8)-Haloalkyl, (Ci-Cs)-Alkoxy, (Ci-C8)-Haloalkoxy, (C3-C8)- Cycloalkoxy, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxy, Aryloxy, Heteroraryloxy, wherein , R 2 , R 3 independently of one another represent hydrogen, halogen, (C 1 -C 6 -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C 3 -C 8 ) -halocycsoalkyl, (C 2 -C 8) alkenyl, (C2-C8) -alkynyl, optionally substituted phenyl, aryl (Ci-C8) alkyl, aryl (C2-C8) alkenyl, heteroaryl, heteroaryl (Ci- C8) alkyl, heterocyclyl, heterocyclyl (Ci-C8) alkyl, (Ci-C 8 () alkoxy- Ci-C 8) alkyl, (CrC 8) alkylthio, (Ci-C 8) - haloalkylthio, (Ci-C 8) haloalkyl, (Ci-Cs) alkoxy, (Ci-C8) -haloalkoxy, (C 3 -C 8) - cycloalkoxy, (C3-C8) -cycloalkyl- (Ci- C 8 ) alkoxy, aryloxy, heteroaryloxy,
(Ci-C8)-Alkoxy-(Ci-C8)-alkoxy, (C2-C8)-Alkinyl-(Ci-C8)-alkoxy, (C2-C8)- ASkenyloxy, Bis-[(Ci-C8)-alkyl]amino-(Ci-C8)-alkoxy, Tris-[(Ci-C8)-alkyl]silyl, Bis- [(Ci-C8)-alkyl]arylsilyl, Bis-[(Ci-C8)-alkyl]-(Ci-C8)-alkylsilyl, Tris-[(Ci-C8)- alkyl]silyl-(C2-C8)-alkinyl, Aryl-(C2-C8)-alkinyl, Heteroaryl-(C2-C8)-alkinyl, (Ci-C8)- Alkyl-(C2-C8)-alkinyl, (C3-C8)-Cycloalkyl-(C2-C8)-alkinyl, (Ci-C8)-Haloalkyl- (C2-C8)-alkinyl, Heterocyclyl-N-(Ci-C8)-alkoxy, Nitro, Cyano, Amino, (Ci-C8)- Alkylamino, Bis-[(Ci-C8)-alkyl]amino, (Ci-Cs)- Alkylcarbonylamino, (C3-C-8)- Cycloalkylcarbonylamino, Arylcarbonylamino, (Ci-C-8)-Alkoxycarbonylamino, Heterocyclyl-(Ci-C8)-alkoxy, (C3-C8)- Cycloalkyl-(Ci-C8)-alkyl, (C2-C8)- Haloalkenyl, (C3-C8)-Haloalkinyl, Heterocyclyl-(C2-C8)-alkinyl, (C3-C8)- Halocycloalkoxy, (C2-C8)-Haloalkinyloxy, Arylthio, Heteroarylthio, (Ci-Cs)- Alkylsulfinyl, (d-CsJ-Haloalkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, (Ci-Ce)- Alkylsulfonyl, (Ci-CeJ-Haloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (Ci-C 8) alkoxy (Ci-C 8) alkoxy, (C 2 -C 8) alkynyl (Ci-C 8) alkoxy, (C 2 -C 8) - ASkenyloxy, bis [ (C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkoxy, tris - [(C 1 -C 8 ) -alkyl] silyl, bis [(C 1 -C 8 ) -alkyl] arylsilyl, bis- [(Ci-C 8) alkyl] - (Ci-C8) alkylsilyl, tris - [(Ci-C 8) - alkyl] silyl (C 2 -C 8) alkynyl, aryl (C 2 - C 8) alkynyl, heteroaryl (C 2 -C 8) -alkynyl, (Ci-C 8) - alkyl (C 2 -C 8) -alkynyl, (C3-C8) cycloalkyl (C 2 - C 8 ) -alkynyl, (C 1 -C 8 ) -haloalkyl- (C 2 -C 8 ) -alkynyl, heterocyclyl-N- (C 1 -C 8 ) -alkoxy, nitro, cyano, amino, (C 1 -C 8 ) - alkylamino, bis - [(C 1 -C 8 ) -alkyl] amino, (C 1 -C 8) -alkylcarbonylamino, (C 3 -C 8 -cycloalkylcarbonylamino, arylcarbonylamino, (C 1 -C 8 -alkoxycarbonylamino, heterocyclyl- Ci-C 8) alkoxy, (C 3 -C 8) - cycloalkyl, (Ci-C 8) alkyl, (C 2 -C 8) - haloalkenyl, (C 3 -C 8) haloalkynyl, heterocyclyl ( C 2 -C 8 ) -alkynyl, (C 3 -C 8 ) -halocycloalkoxy, (C 2 -C 8 ) -haloalkynyloxy, arylthio, heteroarylthio, (C 1 -C 8 ) -alkylsulfinyl, (C 1 -C 5 -alkylsulfinyl, arylsulfinyl, Heteroarylsulfinyl, (C 1 -C 6) -alkylsulfonyl, (C 1 -C 6 -haloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl,
Thiocyanato, Isothiocyanato, (C3-C8)-Cycloalkylamino, (C3-C8)- Cycloalkyl[(Ci-C8)-alkyl]amino, (C2-C8)-Alkenylamino stehen, R1 und R2 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, R2 und R3 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, W für Sauerstoff, Schwefe! sieht, Thiocyanato, isothiocyanato, (C 3 -C 8) -cycloalkylamino, (C 3 -C 8) -cycloalkyl [(C 1 -C 8) -alkyl] amino, (C 2 -C 8) -alkenylamino, R 1 and R 2 contain the atoms they are bonded, form a fully saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring, R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or form unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring, W for oxygen, sulfur! sees
X für N-R4 steht, X is NR 4 ,
R4 für Wasserstoff, (Ci-C8)-Alkyl, (C3-C8)-Cycloalkyl, (C3-C8)-Cyc!oa!ky!-(Ci-C8)- alkyl, (C4-C8)-Cycloalkenyl, Cyano-(Ci-C8)-a!kyl, (C2-C8)-Alkenyl-(Ci-C8)-alkyl, (Ci-C8)-Ha!oa!kyl, (C2-C8)-Alkinyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkyS, Heteroaryl- (Ci-Cs)-a!kyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)-ASkylcarbonyl, (C3-C8)- Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, Heterocyclylcarbonyl, Aryl-(Ci-C8)-alkylcarbonyl, (Ci-C8)-Alkoxycarbonyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl, (C3-C8)- Cycloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (Ci-C8)- Alkoxycarbonylcarbonyl, Aryl-(Ci-C8)-alkoxycarbonylcarbonyl, (Ci-C8)- Alkylaminothiocarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C-3-C8)- Cycloalkylaminocarbonyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Bis-[(Ci-C8)- Alkyljaminocarbonyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C8)- Cycloalkoxycarbonyl-(Ci-C8)-alkyl steht, R 4 represents hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) -Cyc oa ky -! (Ci-C8) - alkyl, (C 4 -C 8) cycloalkenyl, cyano (Ci-C8) -a! kyl, (C 2 -C 8) alkenyl (Ci-C 8) alkyl, (Ci-C 8) -Ha! oa ! kyl, (C 2 -C 8) alkynyl (Ci-C 8) alkyl, aryl (Ci-C 8) -alkyS, heteroaryl (Ci-Cs) -a! kyl, heterocyclyl (Ci- C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, (C 3 -C 8 ) -cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C 1 -C 8 ) -haloalkylcarbonyl, heterocyclylcarbonyl, aryl- (C 1 -C 8 ) -alkylcarbonyl , (C 1 -C 8 ) -alkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkoxycarbonyl, (C 3 -C 8 ) -cycloalkoxycarbonyl, (C 1 -C 8 ) -alkoxycarbonyl- (C 1 -C 8 -alkyl) 8) alkyl, (Ci-C8) alkylsulfonyl, (C 3 -C 8) - cycloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (Ci-C 8) - alkoxycarbonylcarbonyl, aryl (Ci-C 8) -alkoxycarbonylcarbonyl, (C -C 8) - alkylaminothiocarbonyl, (Ci-C 8) alkylaminocarbonyl, (C-3 C-8) - cycloalkylaminocarbonyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, - bis [(C -C 8 ) - alkylaminocarbonyl, aryl, heteroaryl l, heterocyclyl, (C3-C8) - cycloalkoxycarbonyl (Ci-C 8) -alkyl,
Q für (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C3-C8)-Cycloalkyl, (C3-C8)-Cycloalkyl-(Ci-C8)- alkyl, (C4-C8)-Cycloalkenyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C8)- alkyi, Heteroaryi-(Ci-C8)-aikyl, Heterocyclyl-(Ci-C8)-alkyl, Heteroaryl, Q is (Ci-C 8) alkyl, (C 2 -C 8) -alkenyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) -cycloalkyl- (Ci-C8) - alkyl, (C 4 -C 8 ) -cycloalkenyl, optionally substituted phenyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryi (C 1 -C 8 ) -acyl, heterocyclyl- (C 1 -C 8 ) -alkyl, heteroaryl,
Heterocyclyl, Heterocyclylaryl, Heterocyclylheteroaryl, Heteroarylheteroaryl, Heteroarylaryl, Arylaryl, Aryloxyaryl, Aryl-(C2-C8)-alkenyl, Heteroaryl-(C2-C8)- alkenyl, Heterocyclyl-(C2-C8)-alkenyl, Aryl-(C2-C8)-alkinyl, Heteroaryl-(C2-C8)- alkinyl, Heterocyclyl-(Ci-C8)-alkinyl, (C3-C8)-Cycloalky!-(C2-C8)-a!kinyl, (Ci-C8)- Alkylamino-(Ci-C8)-alkyl, Bis-[(Ci-C8)-alkyl]amino-(Ci-C8)-alkyl, Hydroxy- (Ci-Cs)-alkyl, (Ci-C8)-A!koxy-(Ci-C8)-a!kyl, Tris-[(Ci-C8)-alkyl]silyloxy-(Ci-C8)- alkyl, Bis-[(Ci-C8)-alkyl]arylsilyloxy-(Ci-C8)-alkyl, Bis-[(Ci-C8)-alkyl]-(Ci-C8)- alkylsilyloxy-(Ci-C8)-alkyl, Bis-[(Ci-C8)-alkyl]amino-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, (Ci-C8)-A!koxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, Aryloxy-(Ci-C8)-alkyl, Heterocyclyl, heterocyclylaryl, heterocyclylheteroaryl, heteroarylheteroaryl, heteroarylaryl, arylaryl, aryloxyaryl, aryl- (C 2 -C 8 ) -alkenyl, heteroaryl- (C 2 -C 8 ) -alkenyl, heterocyclyl- (C 2 -C 8 ) -alkenyl, aryl- C2-C8) alkynyl, heteroaryl (C2-C8) - alkynyl, heterocyclyl (Ci-C8) -alkynyl, (C 3 -C 8) -Cycloalky - (C2-C8) -a! kinyl, (Ci-C8) - alkylamino (Ci-C8) alkyl, - bis [(Ci-C 8) alkyl] amino- (Ci-C 8) alkyl, hydroxy (Ci-Cs) alkyl, (Ci-C 8) -A alkoxy- (Ci-C8) -a alkyl, tris - [(Ci-C 8) alkyl] silyloxy (Ci-C 8) - alkyl, bis- [(Ci-C 8) alkyl] arylsilyloxy- (Ci-C 8) alkyl, - bis [(Ci-C 8) alkyl] - (Ci-C 8) - alkylsilyloxy (Ci-C8) - alkyl, - bis [(C 8) alkyl] amino (C 8) alkoxy (Ci-C8) alkyl, (Ci-C 8) -A alkoxy- (C 8! ) -alkoxy- (C 1 -C 8 ) -alkyl, aryloxy- (C 1 -C 8 ) -alkyl,
Heteroaryloxy-(Ci-C8)-alkyl, (Ci-C8)-A!kylthio-(Ci-C8)-alkyl, Arylthio-(Ci-Cs)- alkyl, Heteroarylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkoxycarbonyl-N-heterocyclyl, Aryl- (Ci-C8)-alkoxycarbonyl-N-heterocyclyl, (Ci-C8)-Alkyl-N-heterocyclyl, (Ci-C8)- Alkylsu!fonyl-N-heterocyclyl, Arylsulfonyl-N-heterocyclyl, Heteroarylsulfonyl-N- heterocyclyl, (C3-C8)-Cycloalkylsulfonyl-N-heterocyclyl, (Ci-C8)- Haloalkylsulfonyl-N-heterocyclyl, (Ci-CeJ-Alkylcarbonyl-N-heterocyclyl, ! Heteroaryloxy (C 8) alkyl, (Ci-C 8) -A kylthio- (Ci-C8) alkyl, arylthio (Ci-Cs) - alkyl, heteroarylthio (C 8) - alkyl, (C 1 -C 8 ) -alkoxycarbonyl-N-heterocyclyl, aryl- (C 1 -C 8 ) -alkoxycarbonyl-N-heterocyclyl, (C 1 -C 8 ) -alkyl-N-heterocyclyl, (C 1 -C 8 ) - Alkylsulfonyl-N-heterocyclyl, arylsulfonyl-N-heterocyclyl, heteroarylsulfonyl-N-heterocyclyl, (C 3 -C 8 ) -cycloalkylsulfonyl-N-heterocyclyl, (C 1 -C 8 ) -haloalkylsulfonyl-N-heterocyclyl, (C 1 -C 5 ) -cycloalkylsulfonyl-N-heterocyclyl alkylcarbonyl-N-heterocyclyl,
Arylcarbonyl-N-heterocyclyS, Heteroarylcarbonyl-N-heterocyclyl, (C3-C-8)- Cycloalkylcarbonyl-N-heterocyclyl, (Ci-C8)-Cycloalkyl-N-heterocyclyl, Aryl-N- heterocyclyl, Aryl-(Ci-C8)-alkyl-N-heterocyclyl, Bis-[(Ci-C8)-alkyl]aminoalkyl-N- heterocyclyl, Bis-[(Ci-C8)-alkyl]aminosu!fony!-N-heterocyclyl, Heteroaryloxyaryl, Heteroaryloxyheteroaryl, Aryloxyheteroaryl, (Ci-C8)-Alkylsulfinyl, (Ci-C8)- Alkylthio, (Ci-C8)-A!kylsulfonyl, (C3-C8)-Cycloalkylsulfinyl, (C3-C8)-Cycloalkylthio, (C3-C8)-Cycloalkylsulfonyl, Arylsulfinyl, Arylthio, Arylsulfonyl, Amino, (Ci-C8)- Alkylamino, Bis-[(Ci-C8)-A!kyl]amino, Arylamino, Aryl-(Ci-C8)-alkylamino, (C3-C8)-Cycloalkylamino, Formyl, (Ci-C8)-Alkylcarbonyl, Arylcarbonyl, Imino- (Ci-C8)-alkyl, (Ci-C8)-Alkylimino-(Ci-C8)-alkyl, Arylimino-(Ci-C8)-alkyl, (Ci-C8)- Alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (C3-C8)-Cycloalkyl-(Ci-C8)- alkoxycarbonyl, Aryl-(Ci-C8)-alkoxycarbonyl, Aryl-(Ci-C8)-alkylaminocarbonyl, Aminocarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C3-C8)-Cycloalky!aminocarbonyl, Bis-[(Ci-C8)-alkyl]aminocarbonyl, Heterocyclyl-N-carbonyl, Imino, (Ci-C8)- Alkylimino, Arylimino, (C3-C8)-Cycloalkylimino, (C3-C8)-Cycloalkyl-(Ci-C8)- alkylimino, Hydroxyimino, (Ci-C8)-Alkoxyimino, (C2-C8)-Alkenyloxyimino, (C3-C8)-Cycloalkoxyimino, (C3-C8)-Cyloalkyl-(Ci-C8)-alkoxyiminoi Aryloxyimino, Aryl-(Ci-C8)-a!koxyimino, Heteroaryl-(Ci-C8)-a!koxyimino, Heteroaryloxyimino, Heteroarylimino, Heterocyclylimino, Heterocyclyl-(Ci-C8)-alkylimino, Arylcarbonyl-N-heterocyclyl, heteroarylcarbonyl-N-heterocyclyl, (C3-C-8) cycloalkylcarbonyl-N-heterocyclyl, (C 1 -C 8 ) -cycloalkyl-N-heterocyclyl, aryl-N-heterocyclyl, aryl- C8) alkyl-N-heterocyclyl, - bis [(Ci-C 8) alkyl] amino alkyl-N-heterocyclyl, bis - [(Ci-C8) alkyl] sulfonyl aminosu -N-heterocyclyl, Heteroaryloxyaryl, Heteroaryloxyheteroaryl! , Aryloxyheteroaryl, (Ci-C8) alkylsulfinyl, (Ci-C 8) - alkylthio, (Ci-C 8) -A kylsulfonyl, (C3-C8) cycloalkylsulfinyl, (C 3 -C 8) -cycloalkylthio , (C 3 -C 8) -cycloalkylsulfonyl, arylsulfinyl, arylthio, arylsulfonyl, amino, (C 1 -C 8 ) -alkylamino, bis - [(C 1 -C 8 ) -alkyl] amino, arylamino, aryl- (C 1 -C 8 ) alkylamino, (C 3 -C 8 ) -cycloalkylamino, formyl, (C 1 -C 8 ) -alkylcarbonyl, arylcarbonyl, imino- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylimino- (C 1 -C 8 ) alkyl, Arylimino- (Ci-C 8) alkyl, (Ci-C8) - alkoxycarbonyl, (C3-C8) -cycloalkoxycarbonyl, (C3-C8) -cycloalkyl- (Ci-C8) - alkoxycarbonyl, Aryl- (C 1 -C 8 ) -alkoxycarbonyl, aryl- (C 1 -C 8 ) -alkylaminocarbonyl, aminocarbonyl, (C 1 -C 8 ) -alkylaminocarbonyl, (C 3 -C 8 ) -cycloalkyl-aminocarbonyl, bis - [(C 1 -C 8 ) -alkyl] -aminocarbonyl, heterocyclyl-N-carbonyl, imino, (C 1 -C 8 ) -alkylimino , Arylimino, (C 3 -C 8 ) -cycloalkylimino, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkylimino, hydroxyimino, (C 1 -C 8 ) -alkoxyimino, (C 2 -C 8 ) -alkenyloxyimino, (C3-C8) -Cycloalkoxyimino, (C 3 -C 8) -Cyloalkyl- (Ci-C 8) alkoxyimino i aryloxyimino, aryl (Ci-C8) -a koxyimino, heteroaryl (Ci-C 8! ) -a! koxyimino, heteroaryloxyimino, heteroarylimino, heterocyclylimino, heterocyclyl (Ci-C 8 ) -alkylimino,
Aminoimino, (Ci-C8)-Alkylaminoimino, Arylaminoimino, Heteroarylaminoimino, (C3-C8)-Cycloalkylaminoimino, Bis-[(Ci-C8)-Alkyl]aminoimino, Aryl-(d-C8)- alkylaminoimino, Aryl[(Ci-C8)-alkyl]aminoimino, (C3-C8)-Cycloalkyl[(Ci-C8)- alkyljaminoimino, (C3-C8)-Cycloalkyl-(Ci-C8)-alkylaminoimino, Aminoimino, (C 1 -C 8 ) -alkylaminoimino, arylaminoimino, heteroarylaminoimino, (C 3 -C 8 ) -cycloalkylaminoimino, bis - [(C 1 -C 8 ) -alkyl] aminoimino, aryl- (C 1 -C 8 ) -alkylaminoimino, aryl [( Ci-C 8) alkyl] aminoimino, (C3-C8) -cycloalkyl [(Ci-C 8) - alkyljaminoimino, (C3-C8) -cycloalkyl- (Ci-C 8) -alkylaminoimino,
Heterocyclylaminoimino, Heteroaryl-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, Aryl-(Ci-C8)- alkoxy-(Ci-C8)-alkyl, Heterocyclyl-N-(Ci-C8)-alkyl, Aryl-[(Ci-C8)-alkyl]amino- (Ci-Cs)-alkyl, Aryl-(Ci-C8)-alkyl[(Ci-C8)-alkyl]amino-(Ci-C8)-alkyl, (Ci-C8)- Alkoxycarbonyl-(Ci-C8)-alkylamino-(Ci-C8)-alkyl, (Ci-C8)-Alkoxycarbonyl- (Ci-C8)-a!kyl[(Ci-C8)-alkyl]amino-(Ci-C8)-alkyl, Heteroaryl-[(Ci-C8)-alkyl]amino- (Ci-Cs)-alkyl, Heteroaryl-(Ci-C8)-alkyl-[(Ci-C8)-alkyl]amino-(Ci-C8)-alkyl, - (C3-C8)-Cycloalkyl-[(Ci-C8)-alkyl]amino-(Ci-C8)-alkyl, (C3-C8)-Cycloalkylamino- (Ci-Cs)-alkyl, Aryl-(Ci-C8)-alkoxy-(Ci-C8)-alkylaryl, Heterocyclyl-N-(Ci-C8)- alkylaryl, Aryl[(Ci-C8)-alky!]amino-(Ci-C8)-alkylaryl, Aryl-(Ci-C8)-alkyl[(Ci-C8)- alkyl]amino-(Ci-C8)-alkylaryl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkylamino- (Ci-Cs)-a!kylaryl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl[(Ci-C8)-alkyl]amino- (Ci-C8)-alkylaryl, Heteroaryl[(Ci-C8)-alkyl]amino-(Ci-C8)-alkylaryl, Heteroaryl-Heterocyclylaminoimino, heteroaryl- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, heterocyclyl-N- (C 1 -C 4) 8 ) -alkyl, aryl - [(Ci-C 8 ) -alkyl] amino- (Ci-Cs) -alkyl, aryl- (Ci-C 8 ) -alkyl [(Ci-C 8 ) -alkyl] amino- ( Ci-C 8) alkyl, (Ci-C8) - alkoxycarbonyl, (Ci-C 8) alkylamino (Ci-C8) alkyl, (Ci-C8) alkoxycarbonyl (Ci-C 8) -alkyl [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkyl, heteroaryl- [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkyl, heteroaryl- Ci-C 8) alkyl - [(Ci-C 8) alkyl] amino- (Ci-C 8) -alkyl, - (C 3 -C 8) cycloalkyl, - [(Ci-C 8) alkyl] amino- (Ci-C 8) alkyl, (C 3 -C 8) cycloalkylamino- (Ci-Cs) alkyl, aryl (Ci-C 8) alkoxy (Ci-C8) alkylaryl, heterocyclyl -N- (Ci-C 8 ) - alkylaryl, aryl [(Ci-C8) -alky!] amino- (Ci-C 8 ) -alkylaryl, aryl- (Ci-C 8 ) -alkyl [(Ci-C 8 ) - alkyl] amino- (Ci-C8 ) -alkylaryl, (C 1 -C 8) -alkoxycarbonyl- (C 1 -C 8) -alkylamino- (C 1 -C 8) -alkylamino, (C 1 -C 8) -alkoxycarbonyl- (C 1 -C 8) -alkyl [(Ci-C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkylaryl, heteroaryl [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkylaryl, heteroaryl
(Ci-C8)-alkyl[(Ci-C8)-alkyl]amino-(Ci-C8)-alkylaryl, (C3-C8)-Cycloalkyl[(Ci-C8)- alkyl]amino-(Ci-C8)-alkylaryl, (C3-C8)-Cycloalkylamino-(Ci-C8)-alkylaryl, (Ci-C8)- A!koxy[(Ci-C8)-alkoxy]-(Ci-C8)-alkylaryl steht (Ci-C 8) alkyl [(Ci-C 8) alkyl] amino- (Ci-C8) alkylaryl, (C3-C8) -cycloalkyl [(Ci-C 8) - alkyl] amino- ( C 1 -C 8 ) -alkylaryl, (C 3 -C 8 ) -cycloalkylamino- (C 1 -C 8 ) -alkylaryl, (C 1 -C 8 ) -alkoxy [(C 1 -C 8 ) -alkoxy] - (ci) C 8 ) alkylaryl
Z1 und Z2 zusammen eine N-(Bis-(Ci-C8)-aikyl)sulfanyliden-, N-(Aryl-(Ci-C8)- alkyl)sulfanyiiden-, N-(Bis-(C3-C8)-Cycloalkyl)sulfanyliden-, N-((Ci-C8)-Alkyl- (C3-C8)-cycloalkyl)sulfanylidengruppe oder eine N,N-di-(Ci-C-8)- alkylformylidengruppe bilden. Z 1 and Z 2 together form a N- (bis (C 1 -C 8 ) -acyl) sulfanylidene, N- (aryl- (C 1 -C 8 ) -alkyl) sulfanylidene, N- (bis (C 3 -C 8 ) Cycloalkyl) sulfanylidene, N - ((C 1 -C 8 ) alkyl (C 3 -C 8 ) cycloalkyl) sulfanylidene group or an N, N-di (C 1 -C 8) alkylformylidene group.
Bevorzugt sind erfindungsgemäße Verbindungen der aligemeinen Formel (I), worin Preference is given to compounds according to the invention of the general formula (I) in which
R\ R2, R3 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C4)-Alkyl, (C3-C-8)- Cycloalkyl, (C4-C8)-Cycloalkenyl, (C3-C8)-Halocycloalkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C4)-alkyl, Aryl- (C2-C4)-alkenyl, Heteroaryl, Heteroaryl-(Ci-C4)-alkyl, Heterocyclyl, Heterocyclyl- (Ci-C4)-alkyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio, (C1-C4)- Haloalkylthio, (Ci-C4)-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (C3-C8)- Cycloalkoxy, (C3-C8)-Cycloalkyl-(Ci-C)-alkoxy, Aryloxy, Heteroraryloxy, (Ci-C4)-Alkoxy-(Ci-C4)-alkoxy, (C2-C)-Alkinyl-(Ci-C4)-alkoxy, (C2-C4)- Alkenyloxy, Bis-[(Ci-C4)-alkyl]amino-(Ci-C4)-alkoxy, Tris-[(Ci-C )-alkyl]silyl, Bis- [(Ci-C)-alkyl]arylsilyl, Bis-[(Ci-C4)-alkyl]-(C1-C4)-alkylsilyl, Tris-[(Ci-C4)- alkyl]silyl-(C2-C)-alkinyl, Aryl-(C2-C4)-alkinyl, Heteroaryl-(C2-C4)-alkinyl, (Ci-C )- Alkyl-(C2-C4)-alkinyl, (C3-C8)-Cycloalkyl-(C2-C )-alkinyl, (Ci-C4)-Haloalkyl- (C2-C4)-alkinyl, Heterocyclyl-N-(Ci-C4)-alkoxy, Nitro, Cyano, Amino, (Ci-C4)- Alkylamino, Bis-[(Ci-C4)-alkyl]amino, (Ci-C4)- Alkylcarbonylamino, (C3-C8)- Cycloalkylcarbonylamino, Arylcarbonylamino, (Ci-C4)-Alkoxycarbonylamino, Heterocyclyl-(Ci-C)-alkoxy, (C3-C8)- Cycloalkyl-(Ci-C4)-alkyl, (C2-C )- Haloalkenyl, (C2-C4)-Haloalkinyl, Heterocyclyl-(C2-C4)-alkinyl, (C3-C )- Halocyc!oalkoxy, (C2-C4)-Haloalkinyloxy, Arylthio, Heteroarylthio, (C1-C4)- Alkylsulfinyl, (Ci-C4)-Haloalkylsu!finyl, Arylsulfinyl, Heteroarylsulfinyl, (C1-C4)- Alkylsulfonyl, (Ci-C4)-Haloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, R 1 , R 3 and R 3 independently of one another are hydrogen, halogen, (C 1 -C 4 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C 3 -C 8 ) - Halocycloalkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, optionally substituted phenyl, aryl- (C 1 -C 4 ) -alkyl, aryl- (C 2 -C 4 ) -alkenyl, heteroaryl, heteroaryl- (C 1 -C 4 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylthio, ( C 1 -C 4 ) - haloalkylthio, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkoxy, (C 3 -C 8 ) -cycloalkoxy, (C 3 -C 8 ) -cycloalkyl (Ci-C) alkoxy, aryloxy, Heteroraryloxy, (Ci-C 4) alkoxy (Ci-C 4) alkoxy, (C 2 -C) alkynyl (Ci-C 4) alkoxy, (C 2 -C 4) - alkenyloxy, bis - [(Ci-C4) alkyl] amino- (Ci-C 4) alkoxy, tris - [(Ci-C) alkyl] silyl, bis [(Ci- C) alkyl] arylsilyl, bis - [(Ci-C 4) alkyl] - (C 1 -C 4) alkylsilyl, tris - [(Ci-C4) - alkyl] silyl (C 2 -C) -alkynyl, aryl- (C 2 -C 4 ) -alkynyl, heteroaryl- (C 2 -C 4 ) -alkynyl, (Ci-C) -alkyl- (C 2 -C 4 ) -alkynyl, (C 3 -C 8 ) cycloalkyl- (C 2 -C) alkynyl, (Ci-C 4) haloalkyl (C2-C4) alkynyl, heterocyclyl-N- (Ci-C 4) alkoxy, nitro, cyano, amino, (Ci-C4) - alkylamino, bis - [(C 1 -C 4 ) -alkyl] amino, (C 1 -C 4 ) -alkylcarbonylamino, (C 3 -C 8 ) -cycloalkylcarbonylamino, arylcarbonylamino, (C 1 -C 4 ) -alkoxycarbonylamino, heterocyclyl- (C 1 -C 4 ) - alkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 4 ) -alkyl, (C 2 -C) -haloalkenyl, (C 2 -C 4 ) -haloalkynyl, heterocyclyl- (C 2 -C 4 ) - alkynyl, (C 3 -C) - Halocycloalkoxy, (C 2 -C 4) -haloalkynyloxy, arylthio, heteroarylthio, (C 1 -C 4) -alkylsulfinyl, (C 1 -C 4) -haloalkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, (C 1 -C 4) -alkylsulfonyl, (C 1 -C 4) -alkyl ) Haloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl,
Thiocyanato, Isothiocyanato, (C3-C8)-Cycloalkylamino, (C3-C8)- Cycloalkyl[(Ci-C4)-alkyl]amino, (C2-C4)-Alkenylamino stehen, Thiocyanato, isothiocyanato, (C 3 -C 8 ) -cycloalkylamino, (C 3 -C 8 ) -cycloalkyl [(C 1 -C 4) -alkyl] -amino, (C 2 -C 4) -alkenylamino,
R1 und R2 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden,  form interrupted and optionally further substituted 5 to 7-membered ring,
R2 und R3 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden,  form interrupted and optionally further substituted 5 to 7-membered ring,
W für Sauerstoff, Schwefel steht, X für N-R4 steht, W is oxygen, sulfur, X is NR 4 ,
R4 für Wasserstoff, (Ci-C4)-Alkyl, (C3-C8)-Cycloalkyl, (C3-C8)-Cycloalkyl-(Ci-C4)- alkyl, (C4-C8)-Cycloalkenyl, Cyano-(Ci-C4)-alkyl, (C2-C4)-Alkenyl-(Ci-C4)-alkyl, (Ci-C4)-Haloalkyl, (C2-C4)-Alkinyl-(Ci-C4)-alkyl, Aryl-(Ci-C4)-alkyl, Heteroaryl- (Ci-C4)-alkyl, Heterocyclyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylcarbonyl, (C3-C8)- Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (Ci-C4)-Haloalkylcarbonyl, Heterocyclylcarbonyl, Aryl-(Ci-C4)-alkylcarbonyl, (Ci-C4)-Alkoxycarbonyl, (C3-C8)-Cycloalkyl-(Ci-C4)-alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, R 4 represents hydrogen, (Ci-C 4) -alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) -cycloalkyl- (Ci-C4) - alkyl, (C4-C8) - cycloalkenyl, cyano (Ci-C 4) alkyl, (C2-C4) alkenyl (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C2-C4) alkynyl (Ci- C 4) alkyl, aryl (Ci-C 4) alkyl, heteroaryl (Ci-C 4) alkyl, heterocyclyl (Ci-C 4) alkyl, (Ci-C 4) alkylcarbonyl, (C 3 -C 8 ) -cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C 1 -C 4 ) -haloalkylcarbonyl, heterocyclylcarbonyl, aryl- (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 4 ) -alkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 4) -alkoxycarbonyl, (C 3 -C 8 ) -cycloalkoxycarbonyl,
(Ci-C4)-Alkoxycarbonyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl, (C3-C8)- Cycloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (C1-C4)- Alkoxycarbonylcarbonyl, Aryl-(Ci-C4)-alkoxycarbonylcarbonyl, (C1-C4)- Alkylaminothiocarbonyl, (Ci-C4)-Alkylaminocarbonyl, (C3-C8)- Cycloalkylaminocarbonyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, Bis-[(Ci-C4)- Alkyljaminocarbonyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C8)- Cycloalkoxycarbonyl-(Ci-C4)-alkyl steht, für (Ci-C4)-Alkyl, (C2-C4)-Alkenyl! (C3-C8)-Cyc!oalkyl, (C3-C8)-Cycloalkyl-(Ci-C4)- alkyl, (C4-C8)-Cycloalkenyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C )- alkyl, Heteroaryl-(Ci-C4)-alkyl, Heterocyclyl-(Ci-C4)-alkyl, Heteroaryl, (Ci-C4) alkoxycarbonyl (Ci-C 4) alkyl, (Ci-C 4) alkylsulfonyl, (C 3 -C 8) - cycloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C1-C4) - alkoxycarbonylcarbonyl, aryl (C 1 -C 4) -alkoxycarbonylcarbonyl, (C 1 -C 4) -alkylaminothiocarbonyl, (C 1 -C 4) -alkylaminocarbonyl, (C 3 -C 8 ) -cycloalkylaminocarbonyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl , Bis - [(C 1 -C 4 ) -alkylaminocarbonyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 8 ) -cycloalkoxycarbonyl- (C 1 -C 4 ) -alkyl, for (Ci-C 4) alkyl, (C 2 -C 4) -alkenyl! ! (C 3 -C 8) -Cyc Oalkyl, (C 3 -C 8) -cycloalkyl- (Ci-C4) - alkyl, (C 4 -C 8) cycloalkenyl, optionally substituted phenyl, aryl (Ci-C ) - alkyl, heteroaryl- (C 1 -C 4 ) -alkyl, heterocyclyl- (C 1 -C 4 ) -alkyl, heteroaryl,
Heterocyclyl, Heterocyclylaryl, Heterocyclylheteroaryl, Heteroarylheteroaryl, Heteroarylaryl, Arylaryl, Aryloxyaryl, Aryl-(C2-C4)-alkenyl, Heteroaryl-(C2-C4)- alkenyl, Heterocyclyl-(C2-C4)-alkenyl, Aryl-(C2-C4)-alkinyl, Heteroaryl-(C2-C4)- alkinyl, Heterocyclyl-(Ci-C4)-alkinyl, (C3-C8)-Cycloalkyl-(C2-C4)-alkinyl, (C1-C4)- Alkylamino-(Ci-C4)-alkyl, Bis-[(Ci-C4)-alkyl]amino-(Ci-C4)-alkyl, Hydroxy- (Ci-C4)-alkyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, Tris-[(Ci-C4)-alkyl]silyloxy-(Ci-C4)- alkyl, Bis-[(Ci-C4)-alkyl]arylsilyloxy-(Ci-C4)-alkyl, Bis-[(Ci-C4)-alkyl]-(Ci-C4)- alkylsilyloxy-(Ci-C4)-alkyl, Bis-[(Ci-C4)-alkyl]amino-(Ci-C4)-alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkoxy-(Ci-C4)-alkyl, Aryloxy-(Ci-C4)-alkyl, Heterocyclyl, heterocyclylaryl, heterocyclylheteroaryl, heteroarylheteroaryl, heteroarylaryl, arylaryl, aryloxyaryl, aryl- (C 2 -C 4 ) -alkenyl, heteroaryl- (C 2 -C 4 ) -alkenyl, heterocyclyl- (C 2 -C 4 ) -alkenyl, aryl- C 2 -C 4) alkynyl, heteroaryl (C 2 -C 4) - alkynyl, heterocyclyl (Ci-C 4) -alkynyl, (C 3 -C 8) cycloalkyl (C 2 -C 4) alkynyl , (C1-C4) - alkylamino (Ci-C 4) alkyl, - bis [(Ci-C 4) alkyl] amino- (Ci-C 4) alkyl, hydroxy (Ci-C4) - alkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, tris - [(Ci-C 4) alkyl] silyloxy (Ci-C4) - alkyl, - bis [(Ci-C 4 ) -alkyl] arylsilyloxy- (C 1 -C 4 ) -alkyl, bis - [(C 1 -C 4 ) -alkyl] - (C 1 -C 4 ) -alkylsilyloxy- (C 1 -C 4 ) -alkyl, bis- [ (C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl C 4 ) -alkyl, aryloxy- (C 1 -C 4 ) -alkyl,
Heteroaryloxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)-alkyl, Arylthio-(Ci-C4)- alkyl, Heteroarylthio-(Ci-C4)-alkyl, (Ci-C4)-Alkoxycarbonyl-N-heterocyclyl, Aryl- (Ci-C4)-alkoxycarbonyl-N-heterocyclyl, (Ci-C4)-Alkyl-N-heterocyclyl, (C1-C4)- Alkylsulfonyl-N-heterocyclyl, Arylsulfonyl-N-heterocyclyl, Heteroarylsulfonyl-N- heterocyclyl, (C3-C8)-Cycloalkylsulfonyl-N-heterocyclyl, (C1-C4)- Haloalkylsulfonyl-N-heterocyclyl, (Ci-C4)-Alkylcarbonyl-N-heterocyclyl, Heteroaryloxy (Ci-C 4) alkyl, (Ci-C 4) alkylthio (Ci-C 4) alkyl, arylthio (Ci-C4) - alkyl, heteroarylthio (Ci-C 4) -alkyl , (C 1 -C 4 ) -alkoxycarbonyl-N-heterocyclyl, aryl- (C 1 -C 4 ) -alkoxycarbonyl-N-heterocyclyl, (C 1 -C 4 ) -alkyl-N-heterocyclyl, (C 1 -C 4 ) -alkylsulfonyl- N-heterocyclyl, arylsulfonyl-N-heterocyclyl, heteroarylsulfonyl-N-heterocyclyl, (C 3 -C 8) -cycloalkylsulfonyl-N-heterocyclyl, (C 1 -C 4 ) -haloalkylsulfonyl-N-heterocyclyl, (C 1 -C 4 ) -alkylcarbonyl-N -heterocyclyl,
Arylcarbonyl-N-heterocyclyl, Heteroarylcarbonyl-N-heterocyclyl, (C3-Cs)- Cycloalkylcarbonyl-N-heterocyclyl, (Ci-C8)-Cycloalkyl-N-heterocyclyl, Aryl-N- heterocyclyl, Aryl-(Ci-C4)-alkyl-N-heterocyclyl, Bis-[(Ci-C4)-alkyl]aminoalkyl-N- heterocyclyl, Bis-[(Ci-C4)-alkyl]aminosulfonyl-N-heterocyclyl, Heteroaryloxyaryl, Heteroaryloxyheteroaryl, Aryloxyheteroaryl, (Ci-C4)-Alkylsulfinyl, (C1-C4)- Alkylthio, (Ci-C4)-Alkylsulfonyl, (C3-C8)-Cycloalkylsulfinyl, (C3-C8)-CycSoalkylthio, (C3-C8)-Cycloalkylsulfonyl, Arylsulfinyl, Arylthio, Arylsulfonyl, Amino, (C1-C4)- Alkylamino, Bis-[(Ci-C4)-Alkyl]amino, Arylamino, Aryl-(Ci-C4)-alkylamino, (C3-C8)-Cycloalkylamino, Formyl, (Ci-C )-Alkylcarbonyl, Arylcarbonyl, Imino- (Ci-C4)-alkyl, (Ci-C4)-Alkylimino-(Ci-C4)-alkyl, Arylimino-(Ci-C4)-alkyl, (C1-C4)- Alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (C3-C8)-Cycloalkyl-(Ci-C4)- alkoxycarbonyl, Aryl-(Ci-C4)-alkoxycarbonyl, Aryl-(Ci-C4)-alkylaminocarbonyl, Aminocarbonyl, (Ci-C4)-Alkylaminocarbonyl, (C3-C8)-Cycloalkylaminocarbonyl, Bis-[(Ci-C4)-alkyl]aminocarbonyl, Heterocyclyl-N-carbonyl, Imino, (C1-C4)- Alkylimino, Arylimino, (C3-C8)-Cycloalkylimino, (C3-C8)-Cycloalkyl-(Ci-C4)- alkylimino, Hydroxyimino, (Ci-C4)-Alkoxyimino, (C2-C4)-Alkenyloxyimino, Arylcarbonyl-N-heterocyclyl, heteroarylcarbonyl-N-heterocyclyl, (C 3 -Cs) -cycloalkylcarbonyl-N-heterocyclyl, (C 1 -C 8) -cycloalkyl-N-heterocyclyl, aryl-N-heterocyclyl, aryl- (C 1 -C 4 ) -alkyl-N-heterocyclyl, bis - [(C 1 -C 4 ) -alkyl] aminoalkyl-N-heterocyclyl, bis - [(C 1 -C 4 ) -alkyl] aminosulfonyl-N-heterocyclyl, heteroaryloxyaryl, heteroaryloxyheteroaryl, aryloxyheteroaryl, (Ci-C 4) alkylsulfinyl, (C1-C4) - alkylthio, (Ci-C 4) alkylsulfonyl, (C 3 -C 8) cycloalkylsulfinyl, (C 3 -C 8) -CycSoalkylthio, (C 3 - C 8) cycloalkylsulfonyl, arylsulfinyl, arylthio, arylsulfonyl, amino, (C 1 -C 4 ) -alkylamino, bis - [(C 1 -C 4 ) -alkyl] -amino, arylamino, aryl- (C 1 -C 4 ) -alkylamino, (C 3 -C 8) -cycloalkylamino, formyl, (C 1 -C 4 ) -alkylcarbonyl, arylcarbonyl, imino (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylimino (C 1 -C 4 ) -alkyl, arylimino (Ci-C 4) alkyl, (C1-C4) - alkoxycarbonyl, (C 3 -C 8) -cycloalkoxycarbonyl, (C 3 -C 8) -cycloalkyl- (Ci-C4) - alkoxycarbonyl, aryl (Ci- C 4 ) alkoxycarbonyl, aryl- (C 1 -C 4 ) -alkylaminocarbonyl, aminocar carbonyl, (C 1 -C 4 ) -alkylaminocarbonyl, (C 3 -C 8) -cycloalkylaminocarbonyl, bis - [(C 1 -C 4 ) -alkyl] aminocarbonyl, heterocyclyl-N-carbonyl, imino, (C 1 -C 4 ) -alkylimino, Arylimino, (C 3 -C 8 ) -cycloalkylimino, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 4 ) - alkylimino, hydroxyimino, (C 1 -C 4) -alkoxyimino, (C 2 -C 4) -alkenyloxyimino,
(C3-C8)-Cycloalkoxyimino, (C3-C8)-Cyloalkyl-(Ci-C4)-alkoxyimino, Aryloxyimino, Aryl-(Ci-C4)-alkoxyimino, Heteroaryl-(Ci-C4)-alkoxyimino, Heteroaryloxyimino, Heteroarylimino, Heterocyclylimino, Heterocyclyl-(Ci-C4)-alkylimino,  (C 3 -C 8) -cycloalkoxyimino, (C 3 -C 8) -cycloalkyl- (C 1 -C 4) -alkoxyimino, aryloxyimino, aryl- (C 1 -C 4) -alkoxyimino, heteroaryl- (C 1 -C 4) -alkoxyimino, heteroaryloxyimino, heteroarylimino, Heterocyclylimino, heterocyclyl (C 1 -C 4) -alkylimino,
Aminoimino, (Ci-C4)-Alkylaminoimino, Arylaminoimino, Heteroarylaminoimino, (C3-C8)-Cycloalkylaminoimino, Bis-[(Ci-C4)-Alkyl]aminoimino, Aryl-(d-C4)- alkylaminoimino, Aryl[(Ci-C4)-alkyl]aminoimino, (C3-C8)-Cycloalkyl[(Ci-C4)- alkyl]aminoimino, (C3-C8)-Cycloalkyl-(Ci-C4)-alkylaminoimino, Aminoimino, (C 1 -C 4) -alkylaminoimino, arylaminoimino, heteroarylaminoimino, (C 3 -C 8) -cycloalkylaminoimino, bis - [(C 1 -C 4) -alkyl] aminoimino, aryl- (C 1 -C 4) -alkylaminoimino, aryl [(C 1 -C 4) -alkylaminoimino, C 4 ) -alkyl] aminoimino, (C 3 -C 8) -cycloalkyl [(C 1 -C 4 ) -alkyl] aminoimino, (C 3 -C 8) -cycloalkyl- (C 1 -C 4 ) -alkylaminoimino,
Heterocyclylaminoimino, Heteroaryl-(Ci-C4)-alkoxy-(Ci-C4)-alkyl, Aryl-(Ci-C4)- alkoxy-(Ci-C4)-alkyl, HeterocycSyl-N-(Ci-C4)-alkyl, Aryl-[(Ci-C4)-alkyl]amino- (Ci-C4)-alkyl, Aryl-(Ci-C4)-alkyl[(Ci-C4)-alkyl]amino-(Ci-C4)-alkyl, (C1-C4)- Alkoxycarbonyl-(Ci-C4)-alkylamino-(Ci-C4)-alkyl, (Ci-C4)-Alkoxycarbonyl- (Ci-C4)-alkyl[(Ci-C4)-alkyl]amino-(Ci-C4)-alkyl, Heteroaryl-[(Ci-C4)-alkyl]amino- (Ci-C4)-alkyl, Heteroaryl-(Ci-C4)-alkyl-[(Ci-C4)-alkyl]amino-(Ci-C4)-alkyl, - (C3-C8)-Cycloalkyl-[(Ci-C4)-alkyl]amino-(Ci-C4)-alkyl, (C3-C8)-Cycloalkylamino- (Ci-C4)-alkyl, Aryl-(Ci-C4)-alkoxy-(Ci-C4)-alkylaryl, Heterocyclyl-N-(Ci-C4)- alkylaryl, Aryl[(Ci-C4)-alkyl]amino-(Ci-C4)-alkylaryl, Aryl-(Ci-C4)-alkyl[(Ci-C4)- alkyl]amino-(Ci-C4)-alkylaryl, (Ci-C4)-Alkoxycarbonyl-(Ci-C4)-alkylamino- (Ci-C4)-alkylaryl, (Ci-C4)-Alkoxycarbonyl-(Ci-C4)-alky![(Ci-C4)-alkyl]amino- (Ci-C4)-alkylaryl, Heteroaryl[(Ci-C4)-alkyl]amino-(Ci-C4)-alkylaryl, Heteroaryl- (Ci-C4)-alkyl[(Ci-C4)-alkyl]amino-(Ci-C4)-alkylaryl, (C3-C8)-Cycloalkyl[(Ci-C4)- alkyl]amino-(Ci-C4)-alkylaryl, (C3-C8)-Cycloalkylamino-(Ci-C4)-alkylaryl, (C1-C4)- Alkoxy[(Ci-C4)-alkoxy]-(Ci-C4)-alkylaryl steht und Heterocyclylaminoimino, heteroaryl- (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, aryl- (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, heterocycSyl-N- (C 1 -C 4 ) - alkyl, aryl - [(C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkyl, aryl- (C 1 -C 4 ) -alkyl [(C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkyl, (C 1 -C 4) -alkoxycarbonyl- (C 1 -C 4) -alkylamino- (C 1 -C 4) -alkyl, (C 1 -C 4) -alkoxycarbonyl- (C 1 -C 4) -alkyl [(C 1 -C 4) -alkyl ] amino- (C 1 -C 4 ) -alkyl, heteroaryl - [(C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkyl, heteroaryl- (C 1 -C 4 ) -alkyl - [(C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkyl, - (C 3 -C 8) -cycloalkyl - [(C 1 -C 4 ) -alkyl] -amino- (C 1 -C 4 ) -alkyl, (C 3 -C 8 ) Cycloalkylamino- (C 1 -C 4 ) -alkyl, aryl- (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkylaryl, heterocyclyl-N- (C 1 -C 4 ) -alkylaryl, aryl [(C 1 -C 4 ) -cycloalkylamino- (C 1 -C 4 ) -alkyl; ) -alkyl] amino- (C 1 -C 4 ) -alkylaryl, aryl- (C 1 -C 4 ) -alkyl [(C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkylaryl, (C 1 -C 4 ) - Alkoxycarbonyl- (C 1 -C 4 ) -alkylamino- (C 1 -C 4 ) -alkylaryl, (C 1 -C 4 ) -alkoxycarbonyl- (C 1 -C 4 ) -alkyl [(C 1 -C 4 ) -alkyl] amino (C 1 -C 4 ) -alkyl) C4) -alkylaryl, heteroaryl [(C 1 -C 4) -alkyl] amino- (C 1 -C 4) -alkylaryl, heteroaryl- (C 1 -C 4) -alkyl [(C 1 -C 4) -al kyl] amino- (C 1 -C 4) -alkylaryl, (C 3 -C 8 ) -cycloalkyl [(C 1 -C 4) -alkyl] amino- (C 1 -C 4) -alkylaryl, (C 3 -C 8 ) -cycloalkylamino ( C 1 -C 4 ) -alkylaryl, (C 1 -C 4 ) -alkoxy [(C 1 -C 4 ) -alkoxy] - (C 1 -C 4 ) -alkylaryl and
Z1 und Z2 zusammen eine N-(Bis-(Ci-C4)-alkyl)sulfanyliden-, N-(Aryl-(d-C4)- alkyl)sulfanyliden-, N-(Bis-(C3-C8)-Cycloalkyl)sulfanyliden-, N-((Ci-C4)-Alkyl- (C3-C8)-cycloalkyl)sulfanylidengruppe oder eine N,N-di-(Ci-C4)- aikylformylidengruppe bilden. Z 1 and Z 2 together form an N- (bis (C 1 -C 4) alkyl) sulfanylidene, N- (aryl- (C 1 -C 4) -alkyl) sulfanylidene, N- (bis- (C 3 -C 8 ) Cycloalkyl) sulfanylidene, N - ((C 1 -C 4 ) -alkyl- (C 3 -C 8) -cycloalkyl) sulfanylidene group or an N, N-di- (C 1 -C 4 ) -alkylformylidene group.
Im 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: Erfindungsgemäß steht "Arylsulfonyl" für gegebenenfalls substituiertes Phenylsulfonyl oder gegebenenfalls substituiertes polycyclisches Arylsulfonyl, hier insbesondere gegebenenfalls substituiertes Naphthyl-sulfonyl, beispielsweise substituiert durch Fluor, Chlor, Brom, lod, Cyano, Nitro, Alkyl-, Haloalkyl-, Haloalkoxy-, Amino-, 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: According to the invention "arylsulfonyl" is optionally substituted phenylsulfonyl or optionally substituted polycyclic arylsulfonyl, here in particular optionally substituted naphthylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino,
Alkylamino-, Alkylcarbonylamino-, Dialkylamino- oder Alkoxy-gruppen. Alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.
Erfindungsgemäß steht "Cycloalkylsulfonyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für gegebenenfalls substituiertes Cycloalkylsulfonyl, vorzugsweise mit 3 bis 6 Kohlenstoffatomen wie beispielsweise Cyclopropylsulfonyl, Cyclobutylsulfonyl, Cyclopentylsulfonyl oder Cyclohexylsulfonyl. According to the invention "cycloalkylsulfonyl" - alone or as part of a chemical group - is optionally substituted Cycloalkylsulfonyl, preferably having 3 to 6 carbon atoms such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl.
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 Kohlenstoffatomen wie beispielsweise Methylsulfonyl,According to the invention "alkylsulfonyl" - alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably having 1 to 8, or having 1 to 6 carbon atoms such as methylsulfonyl,
Ethylsulfonyl, n-Propylsulfonyl, Isopropylsulfonyl, n-Butylsulfonyl, Isobutylsulfonyl, sec- Butylsulfonyl und tert-Butylsulfonyl. Ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl and tert-butylsulfonyl.
Erfindungsgemäß steht "Heteroarylsulfonyl" für gegebenenfalls substituiertes According to the invention "heteroarylsulfonyl" is optionally substituted
Pyridylsulfonyl, Pyrimidinylsulfonyl, Pyrazinylsulfonyl oder gegebenenfalls Pyridylsulfonyl, pyrimidinylsulfonyl, pyrazinylsulfonyl or optionally
substituiertes polycyclisches Heteroarylsulfonyl, hier insbesondere gegebenenfalls substituiertes Chinolinylsulfonyl, beispielsweise substituiert durch Fluor, Chlor, Brom, lod, Cyano, Nitro, Alkyl-, Haloalkyl-, Haloalkoxy-, Amino-, Alkylamino-, substituted polycyclic heteroarylsulfonyl, here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino,
Alkylcarbonylamino-, Dialkylamino- oder Alkoxygruppen. Alkylcarbonylamino, dialkylamino or alkoxy groups.
Erfindungsgemäß steht "Alkylthio" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes S-Alkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 Kohlenstoffatomen, wie beispielsweise Methylthio, Ethylthio, n- Propylthio, Isopropylthio, n-Butylthio, Isobutylthio, sec-Butylthio und tert-Butylthio. Alkenylthio bedeutet ein über ein Schwefelatom gebundenen Alkenylrest, Alkinylthio bedeutet ein über ein Schwefelatom gebundenen Alkinylrest, Cycloalkylthio bedeutet ein über ein Schwefelatom gebundenen Cycloalkylrest und Cycloalkenylthio bedeutet ein über ein Schwefelatom gebundenen Cycloalkenylrest. „Alkoxy" bedeutet ein über ein Sauerstoffatom gebundenen Alkylrest, Alkenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Alkenylrest, Alkinyloxy bedeutet ein über ein Sauerstoffatom gebundenen Alkinylrest, Cycloalkyloxy bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkylrest und Cycloaikenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkenylrest. According to the invention, "alkylthio" - alone or as part of a chemical group - represents straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n- Butylthio, isobutylthio, sec-butylthio and tert-butylthio. Alkenylthio represents an alkenyl radical bonded via a sulfur atom, alkynylthio represents an alkynyl radical bonded via a sulfur atom, cycloalkylthio represents a cycloalkyl radical bonded via a sulfur atom, and cycloalkenylthio represents a cycloalkenyl radical bonded via a sulfur atom. "Alkoxy" means an alkyl radical bonded via an oxygen atom, alkenyloxy represents an alkynyl radical bound via an oxygen atom, alkynyloxy means an alkynyl radical bound via an oxygen atom, cycloalkyloxy denotes a cycloalkyl radical bonded via an oxygen atom, and cycloalkynyloxy denotes a cycloalkenyl radical bonded via an oxygen atom.
Der Begriff„Aryl" bedeutet ein gegebenenfalls substituiertes mono-, bi- oder The term "aryl" means an optionally substituted mono-, bi- or
polycyclisches aromatisches System mit vorzugsweise 6 bis 14, insbesondere 6 bis 10 Ring-C-Atomen, beispielsweise Phenyl, Naphthyl, Anthryl, Phenanthrenyl, und ähnliches, vorzugsweise Phenyl. polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
Vom Begriff„gegebenenfalls substituiertes Aryl" sind auch mehrcyclische Systeme, wie Tetrahydronaphtyl, Indenyl, Indanyl, Fluorenyl, Biphenylyl, umfasst, wobei die Bindungsstelle am aromatischen System ist. Von der Systematik her ist„Aryl" in der Regel auch von dem Begriff„gegebenenfalls substituiertes Phenyl" umfasst. The term "optionally substituted aryl" also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, the binding site being on the aromatic system. "Aryl" is also generally known from the term "optionally substituted phenyl ".
Bevorzugte Aryl-Substituenten sind hier zum Beispiel Wasserstoff, Halogen, Alkyl, Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl, Halocycloalkyl, Alkenyl, Alkinyl, Aryl,  Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl,
Arylalkyl, Arylalkenyl, Heteroaryl, Heteroarylalkyl, Heterocyclyl, Heterocyclylalkyl, Alkoxyalkyl, Alkylthio, Haloalkylthio, Haloalkyl, Alkoxy, Haloalkoxy, Cycloalkoxy, Cycloalkylalkoxy, Aryloxy, Heteroraryloxy, Alkoxyalkoxy, Alkinylalkoxy, Alkenyloxy, Bis- alkylaminoalkoxy, Tris-[alkyl]silyl, Bis-[alkyl]arylsilyl, Bis-[alkyl]alkylsilyl, Tris- [alkyl]silylalkinyl, Arylalkinyl, Heteroarylalkinyl, Alkylalkinyl, Cycloalkylalkinyl, Arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bisalkylaminoalkoxy, tris [alkyl] silyl, bis [alkyl] arylsilyl, bis [alkyl] alkylsilyl, tris [alkyl] silylalkynyl, arylalkynyl, heteroarylalkynyl, alkylalkynyl, cycloalkylalkynyl,
Haloalkylalkinyl, Heterocyclyl-N-alkoxy, Nitro, Cyano, Amino, Alkylamino, Bis- alkylamino, Alkylcarbonylamino, Cycloalkylcarbonylamino, Arylcarbonylamino, Haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bisalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino,
Alkoxycarbonylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonylalkylamino, Hydroxycarbonyl, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Alkoxycarbonylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl,
Cycloalkylaminocarbonyl, Bis-Alkylaminocarbonyl, Heteroarylalkoxy, Arylalkoxy Cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heteroarylalkoxy, arylalkoxy
Ein heterocyclischer Rest (Heterocyclyl) enthält mindestens einen heterocyclischen 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 gesättigt, ungesättigt, teilgesättigt oder heteroaromatisch ist und dabei unsubstituiert oder substituiert sein kann, wobei die Bindungsstelle an einem Ringatom lokalisiert ist. Ist der Heterocyclylrest oder der heterocyclische Ring gegebenenfalls substituiert, kann er mit anderen carbocyclischen oder heterocyclischen Ringen anneliiert sein. Im Falle von gegebenenfalls substituiertem Heterocyclyl werden auch mehrcyclische Systeme umfaßt, wie beispielsweise 8-Aza-bicyclo[3.2.1]octanyl, 8-Aza- bicyclo[2.2.2]octanyl oder 1-Aza-bicyclo[2.2.1]heptyl. Im Falle von gegebenenfalls substituiertem Heterocyclyl werden auch spirocyclische Systeme umfaßt, wie beispielsweise 1 -Oxa-5-aza-spiro[2.3]hexyl. Wenn nicht anders definiert, enthält der heterocyclische Ring vorzugsweise 3 bis 9 Ringatome, insbesondere 3 bis 6 A heterocyclic radical (heterocyclyl) contains at least one heterocyclic ring (= carbocyclic ring in which at least one C atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P) which is saturated, unsaturated, partially saturated or is heteroaromatic and may be unsubstituted or substituted, wherein the binding site is located on a ring atom. If the heterocyclyl radical or the heterocyclic ring is optionally substituted, it may be anneliiert with other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, more cyclic systems are also included, for example 8-azabicyclo [3.2.1] octanyl, 8-azabicyclo [2.2.2] octanyl or 1-azabicyclo [2.2.1] heptyl. In the case of optionally substituted heterocyclyl, spirocyclic systems are also included, such as 1-oxa-5-aza-spiro [2.3] hexyl. Unless defined otherwise, the heterocyclic ring preferably contains 3 to 9 ring atoms, especially 3 to 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 Ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two oxygen atoms should be directly adjacent, as
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-1 H-pyrrol-1- oder 2- oderfor example with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrole-2 or 3-yl, 2,3-dihydro-1 H-pyrrole 1- or 2- or
3- oder 4- oder 5-yl; 2,5-Dihydro-1 H-pyrrol-1 - oder 2- oder 3-yl, 1 - oder 2- oder 3- oder3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrol-1 - or 2- or 3-yl, 1- or 2- or 3- or
4- Piperidinyl; 2,3,4,5-Tetrahydropyridin-2- oder 3- oder 4- oder 5-yl oder 6-yl; 1 ,2,3,6- Tetrahydropyridin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,2,3,4-4-piperidinyl; 2,3,4,5-tetrahydropyridine-2- or 3- or 4- or 5-yl or 6-yl; 1, 2,3,6-tetrahydropyridine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1, 2,3,4-
Tetrahydropyridin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,4-Dihydropyridin-1 - 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-1 H-azepin-1 - oder 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; Tetrahydropyridine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1,4-dihydropyridine-1 - or 2- or 3- or 4-yl; 2,3-dihydropyridine-2- or 3- or 4- or 5- or 6-yl; 2,5-dihydropyridine-2- or 3- or 4- or 5- or 6-yl, 1- or 2- or 3- or 4-azepanyl; 2,3,4,5-tetrahydro-1H-azepine-1 - or 2- or 3- or 4- or 5- or 6- or 7-yl;
2,3,4,7-Tetrahydro-1 H-azepin-1 - oder 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-tetrahydro-1H-azepine-1 - or 2- or 3- or 4- or 5- or 6- or 7-yl;
2,3,6,7-Tetrahydro-1 H-azepin-1 - 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-1 H-azepin-1- oder 2- oder 3- oder 4-yl; 2,5-Dihydro-1 H-azepin-1 - oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-1 H-azepin-1- oder -2- oder 3- oder 4-yl; 2,3-Dihydro-1 H-azepin- 1 - 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- oder 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; 1 H-Azepin-1- 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 (= 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; 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;2,3,6,7-tetrahydro-1H-azepine-1 - or 2- or 3- or 4-yl; 3,4,5,6-tetrahydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 4,5-dihydro-1H-azepine-1 or 2- or 3- or 4-yl; 2,5-dihydro-1H-azepine-1 or -2 or 3 or 4 or 5 or 6 or 7-yl; 2,7-dihydro-1H-azepine-1 or -2- or 3- or 4-yl; 2,3-dihydro-1H-azepine-1 - 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 or 7-yl; 3,6-dihydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 5,6-dihydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 4,5-dihydro-3H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 1 H-azepine-1 or -2 or 3 or 4 or 5 or 6 or 7-yl; 2H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl; 3H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4H-azepine-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- 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- 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, 1 ,3-Dioxetan-2-yl. Weitere Beispiele für 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-membered and 4-membered 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" 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-1 H- pyrazol-1- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-1 H-pyrazol-1 - oder 2- oder 3- oder 4- oder 5-yl; 1 - oder 2- oder 3- oder 4- Imidazolidinyl; 2,3-Dihydro-1 H-imidazol-1 - oder 2- oder 3- oder 4-yl; 2,5-Dihydro-1 H-imidazol-1 - oder 2- oder 4- oder 5-yl; 4,5-Dihydro- 1 H-imidazol-1 - oder 2- oder 4- oder 5-yl; Hexahydropyridazin-1 - oder 2- oder 3- oder 4-yl; 1 ,2,3,4-Tetrahydropyridazin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,2,3,6- Tetrahydropyridazin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,4,5,6- Tetrahydropyridazin-1 - oder 3- oder 4- oder 5- oder 6-yl; 3,4,5,6-Tetrahydropyridazin-"Heterocyclyl" are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3 or 4 or 5-yl; 4,5-dihydro-1H-pyrazole-1 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; Hexahydropyridazine-1 - or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1, 2,3,6-tetrahydropyridazine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1, 4,5,6-tetrahydropyridazine-1 - or 3- or 4- or 5- or 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; 3,6-Dihydropyridazin-3- oder 4-yl; 1 ,6-Dihydropyriazin-1 - oder 3- oder 4- oder 5- oder 6-yl; Hexahydropyrimidin-1 - oder 2- oder 3- oder 4-yl; 1 ,4,5,6- Tetrahydropyrimidin-1 - oder 2- oder 4- oder 5- oder 6-yl; 1 ,2,5,6-Tetrahydropyrimidin- 1 - oder 2- oder 4- oder 5- oder 6-yl; 1 ,2,3,4-Tetrahydropyrimidin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,6-Dihydropyrimidin-1 - oder 2- oder 4- oder 5- oder 6-yl; 1 ,2-Dihydropyrimidin-1 - oder 2- oder 4- oder 5- oder 6-yl; 2,5-Dihydropyrimidin-2- oder3- or 4- or 5-yl; 4,5-dihydropyridazine-3 or 4-yl; 3,4-dihydropyridazine-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazine-3 or 4-yl; 1,6-dihydropyriazine-1 - or 3- or 4- or 5- or 6-yl; Hexahydropyrimidine-1 - or 2- or 3- or 4-yl; 1, 4,5,6-tetrahydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 1, 2,5,6-tetrahydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyrimidine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1,6-dihydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 1,2-dihydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidine-2- or
4- oder 5-yl; 4,5-Dihydropyrimidin- 4- oder 5- oder 6-yl; 1 ,4-Dihydropyrimidin-1 - oder 2- oder 4- oder 5- oder 6-yl; 1- oder 2- oder 3-Piperazinyl; 1 ,2,3,6-Tetrahydropyrazin-1 - oder 2- oder 3- oder 5- oder 6-yl; 1 ,2,3,4-Tetrahydropyrazin-1 - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1 ,2-Dihydropyrazin-1 - oder 2- oder 3- oder 5- oder 6-yl; 1 ,4- Dihydropyrazin- - oder 2- oder 3-yl; 2,3-Dihydropyrazin-2- oder 3- oder 5- oder 6-yl; 2,5-Dihydropyrazin-2- oder 3-yl; 1 ,3-Dioxolan-2- oder 4- oder 5-yl; 1 ,3-Dioxol-2- oder 4-yl; 1 ,3-Dioxan-2- oder 4- oder 5-yl; 4H-1 ,3-Dioxin-2- oder 4- oder 5- oder 6-yl; 1 ,4- Dioxan-2- oder 3- oder 5- oder 6-yl; 2,3-Dihydro-1 ,4-dioxin-2- oder 3- oder 5- oder 6-yl; 1 ,4-Dioxin-2- oder 3-yl; 1 ,2-Dithiolan-3- oder 4-yl; 3H-1 ,2-Dithiol-3- oder 4- oder 5-yl;4- or 5-yl; 4,5-dihydropyrimidine-4- or 5- or 6-yl; 1,4-dihydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 1- or 2- or 3-piperazinyl; 1,2,3,6-tetrahydropyrazine-1 - or 2- or 3- or 5- or 6-yl; 1,2,3,4-tetrahydropyrazine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1,2-dihydropyrazine-1 - or 2- or 3- or 5- or 6-yl; 1, 4- Dihydropyrazine - or 2- or 3-yl; 2,3-dihydropyrazine-2- or 3- or 5- or 6-yl; 2,5-dihydropyrazine-2 or 3-yl; 1,3-dioxolane-2- or 4- or 5-yl; 1,3-dioxol-2- or 4-yl; 1,3-dioxane-2- or 4- or 5-yl; 4H-1, 3-dioxin-2 or 4 or 5 or 6-yl; 1, 4-dioxane-2 or 3 or 5 or 6-yl; 2,3-dihydro-1,4-dioxin-2- or 3- or 5- or 6-yl; 1, 4-dioxin-2 or 3-yl; 1,2-dithiolan-3 or 4-yl; 3H-1,2-dithiol-3- or 4- or 5-yl;
1.3- Dithiolan-2- oder 4-yl; 1 ,3-Dithiol-2- oder 4-yl; 1 ,2-Dithian-3- oder 4-yl; 3,4-Dihydro- 1 ,2-dithiin-3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-1 ,2-dithiin-3- oder 4-yl; 1 ,2-Dithiin-1,3-dithiolan-2 or 4-yl; 1,3-dithiol-2- or 4-yl; 1,2-dithian-3 or 4-yl; 3,4-dihydro-1,2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro-1,2-dithiin-3 or 4-yl; 1, 2-dithinine
3- oder 4-yl; 1 ,3-Dithian-2- oder 4- oder 5-yl; 4H-1 ,3-Dithiin-2- oder 4- oder 5- oder 6- yl; lsoxazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydroisoxazol-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydroisoxazol-2- oder 3- oder 4- oder 5-yl; 4,5-Dihydroisoxazol-3- oder3- or 4-yl; 1,3-dithian-2- or 4- or 5-yl; 4H-1, 3-dithiine-2 or 4 or 5 or 6 yl; Isoxazolidine-2 or 3 or 4 or 5-yl; 2,3-dihydroisoxazole-2 or 3 or 4 or 5-yl; 2,5-dihydroisoxazole-2 or 3 or 4 or 5-yl; 4,5-dihydroisoxazole-3- or
4- oder 5-yl; 1 ,3-Oxazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-1 ,3-oxazol-2- oder4- or 5-yl; 1,3-oxazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-oxazole-2-or
3- oder 4- oder 5-yl; 2,5-Dihydro-1 ,3-oxazol-2- oder 4- oder 5-yl; 4,5-Dihydro- ,3- oxazol-2- oder 4- oder 5-yl; 1 ,2-Oxazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4- Dihydro-2H-1 ,2-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-1 ,2-oxazin- 2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-1 ,2-oxazin-2- oder 3- oder 4- oder3- or 4- or 5-yl; 2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 4,5-dihydro, 3-oxazol-2 or 4 or 5-yl; 1, 2-oxazinan-2 or 3 or 4 or 5 or 6-yl; 3,4-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1, 2-oxazine-2 or 3 or 4 or
5- oder 6-yl; 5,6-Dihydro-4H-1 ,2-oxazin-3- oder 4- oder 5- oder 6-yl; 2H-1 ,2-Oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 6H-1 ,2-Oxazin-3- oder 4- oder 5- oder 6-yl; 4H-1 ,2- Oxazin-3- oder 4- oder 5- oder 6-yl; 1 ,3-Oxazinan-2- oder 3- oder 4- oder 5- oder 6-yl;5- or 6-yl; 5,6-dihydro-4H-1,2-oxazine-3- or 4- or 5- or 6-yl; 2H-1, 2-oxazine-2 or 3 or 4 or 5 or 6-yl; 6H-1, 2-oxazine-3 or 4 or 5 or 6-yl; 4H-1, 2-oxazine-3 or 4 or 5 or 6-yl; 1,3-oxazinan-2 or 3 or 4 or 5 or 6-yl;
3.4- Dihydro-2H-1 ,3-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-1 ,3- oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-1 ,3-oxazin-2- oder 4- oder3,4-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1, 3-oxazine-2 or 3 or 4 or 5 or 6-yl; 5,6-dihydro-2H-1, 3-oxazine-2 or 4 or
5- oder 6-yl; 5,6-Dihydro-4H-1 ,3-oxazin-2- oder 4- oder 5- oder 6-yl; 2H-1 ,3-Oxazin-2- oder 4- oder 5- oder 6-yl; 6H-1 ,3-Oxazin-2- oder 4- oder 5- oder 6-yl; 4H-1 ,3-Oxazin-2- oder 4- oder 5- oder 6-yl; Morpholin-2- oder 3- oder 4-yl; 3,4-Dihydro-2H-1 ,4-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-1 ,4-oxazin-2- oder 3- oder 5- oder 6- yl; 2H-1 ,4-oxazin-2- oder 3- oder 5- oder 6-yl; 4H-1 ,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-1 ,2- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-1 ,2-oxazepin- 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-1 ,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5,6,7-Tetrahydro-1 ,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5,6,7-Tetrahydro-1 ,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-1 ,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5- Dihydro-1 ,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-1 ,2- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-1 ,2-oxazepin-3- oder5- or 6-yl; 5,6-dihydro-4H-1,3-oxazine-2- or 4- or 5- or 6-yl; 2H-1, 3-oxazine-2- or 4- or 5- or 6-yl; 6H-1, 3-oxazine-2 or 4 or 5 or 6-yl; 4H-1, 3-oxazine-2 or 4 or 5 or 6-yl; Morpholine-2- or 3- or 4-yl; 3,4-dihydro-2H-1,4-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,4-oxazine-2 or 3 or 5 or 6-yl; 2H-1,4-oxazine-2- or 3- or 5- or 6-yl; 4H-1,4-oxazine-2 or 3-yl; 1, 2- oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,2,10-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,2-oxazepine 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-dihydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1, 2-oxazepine-2 or 3 or 4 or 5 or 6 or 7-yl; 4,5-dihydro-1,2-oxazepine-3 or
4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro-1 ,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-y!; 6,7-Dihydro-l ,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-y!; 1 ,2-Oxazepin-3- oder 4- oder 5- oder 6- oder 7-y!; 1 ,3-Oxazepan-2- oder 3- oder 4- oder 5- oder 6- oder 7-y!; 2,3,4,5-Tetrahydro-1 ,3-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-y!; 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,2-oxazepine-3 or 4 or 5 or 6 or 7-y !; 6,7-dihydro-1,2-oxazepine-3 or 4 or 5 or 6 or 7-y !; 1, 2-oxazepine-3 or 4 or 5 or 6 or 7-y !; 1, 3-oxazepan-2 or 3 or 4 or 5 or 6 or 7-y !; 2,3,4,5-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-y;
2,3,4,7-Teirahydro-l ,3-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-y!; 2,3,6,7- Tetrahydro-1 ,3-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-y!; 2,5,6,7-2,3,4,7-tetrahydro-1, 3-oxazepine-2 or 3 or 4 or 5 or 6 or 7-y; 2,3,6,7-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-y; 2,5,6,7
Tetrahydro-1 ,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,5,6,7-Tetrahydro-1 ,3- oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro- ,3-oxazepin-2- oder 3- oderTetrahydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,3,10-oxazepine-2- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-, 3-oxazepine-2 or 3-or
4- oder 5- oder 6- oder 7-yl; 2,5-Dihydro-1 ,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-1 ,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro- ,3- oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro- ,3-oxazepin-2- oder 4- oder4- or 5- or 6- or 7-yl; 2,5-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-, 3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro, 3-oxazepine-2 or 4 or
5- oder 6- oder 7-yl; 6,7-Dihydro-l ,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 1 ,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-1 ,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-1 ,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-1 ,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,5,6,7-5- or 6- or 7-yl; 6,7-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 1,3-oxazepine-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-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 2,5,6,7
Tetrahydro-1 ,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 4,5,6,7-Tetrahydro-1 ,4- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-1 ,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,5-Dihydro-1 ,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-1 ,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-1 ,4- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro-1 ,4-oxazepin-2- oderTetrahydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1, 4-oxazepine-2 or 3 or 4 or 5 or 6 or 7-yl; 2,3-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 2,5-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 2,7-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 4,5-dihydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4,7-Dihydro-1,4-oxazepine-2-Or
3- oder 4- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-1 ,4-oxazepin-2- oder 3- oder 5- oder3- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1, 4-oxazepine-2 or 3 or 5 or
6- oder 7-yl; 1 ,4-Oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; lsothiazolidin-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-1 ,3-thiazol-2- oder 3- oder6- or 7-yl; 1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; isothiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazole-2- or 3- or 4- or 5-yl; 2,5-dihydroisothiazole-2 or 3 or 4 or 5-yl; 4,5-dihydroisothiazole-3 or 4 or 5-yl; 1,3-thiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydro-1, 3-thiazole-2 or 3 or
4- oder 5-yl; 2,5-Dihydro-1 ,3-thiazol-2- oder 4- oder 5-yl; 4,5-Dihydro-1 ,3-thiazol-2- oder 4- oder 5-yl; 1 ,3-Thiazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4-Dihydro-2H- 1 ,3-thiazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-1 ,3-thiazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-1 ,3-thiazin-2- oder 4- oder 5- oder 6-yl; 5,6- Dihydro-4H- ,3-thiazin-2- oder 4- oder 5- oder 6-yl; 2H- ,3-Thiazin-2- oder 4- oder 5- oder 6-yl; 6H-1 ,3-Thiazin-2- oder 4- oder 5- oder 6-yl; 4H-1 ,3-Thiazin-2- oder 4- oder4- or 5-yl; 2,5-dihydro-1,3-thiazole-2 or 4 or 5-yl; 4,5-dihydro-1,3-thiazole-2- or 4- or 5-yl; 1, 3-thiazinan-2 or 3 or 4 or 5 or 6-yl; 3,4-dihydro-2H-1, 3-thiazine-2 or 3 or 4 or 5 or 6-yl; 3,6-dihydro-2H-1, 3-thiazine-2 or 3 or 4 or 5 or 6-yl; 5,6-dihydro-2H-1, 3-thiazine-2 or 4 or 5 or 6-yl; 5,6-dihydro-4H, 3-thiazine-2 or 4 or 5 or 6-yl; 2H, 3-thiazine-2 or 4 or 5 or 6-yl; 6H-1, 3-thiazine-2 or 4 or 5 or 6-yl; 4H-1, 3-thiazine-2 or 4 or
5- oder 6-yl. Weitere Beispiele für "Heterocycly!" sind ein partiell oder vollständig hydrierter heterocyclischer Rest mit 3 Heteroatomen aus der Gruppe N, O und S, wie beispielsweise 1 ,4,2-Dioxazo!idin-2- oder 3- oder 5-yl; 1 ,4,2-Dioxazol-3- oder 5-yl; 1 ,4,2-Dioxazinan-2- oder -3- oder 5- oder 6-yl; 5,6-Dihydro-1 ,4,2-dioxazin-3- oder 5- oder 6-yl; 1 ,4,2-Dioxazin-3- oder 5- oder 6-yl; 1 ,4,2-Dioxazepan-2- oder 3- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-5H-1 ,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl; 2,3- Dihydro-7H- ,4,2-Dioxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-5H- 1 ,4,2-Dioxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 5H-1 ,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl; 7H-1 ,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl. Strukturbeispiele für gegebenenfalls weiter substituierte Heterocyclen sind auch im Folgenden 5- or 6-yl. Further examples of "Heterocycly!" are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as 1, 4,2-Dioxazo! idin-2- or 3- or 5-yl; 1, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,2,2,2-dioxazine-3- or 5- or 6-yl; 1,2,2-dioxazine-3- or 5- or 6-yl; 1, 4,2-dioxazepan-2 or 3 or 5 or 6 or 7-yl; 6,7-dihydro-5H-1, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 2,3-dihydro-7H-, 4,2-dioxazepin-2 or 3 or 5 or 6 or 7-yl; 2,3-dihydro-5H-1,2,2-dioxazepine-2- or 3- or 5- or 6- or 7-yl; 5H-1, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 7H-1, 4,2-dioxazepine-3 or 5 or 6 or 7-yl. Structural examples of optionally further substituted heterocycles are also mentioned below
aufgeführt:  listed:
42 42
Die oben aufgeführten Heterocyclen sind bevorzugt beispielsweise durch Wasserstoff, Halogen, Alkyl, Haloalkyl, Hydroxy, Alkoxy, Cycloalkoxy, Aryloxy, Alkoxyalkyl, The heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl,
Alkoxyalkoxy, Cycloalkyl, Halocycloalkyl, Aryl, Arylalkyl, Heteroaryl, Heterocyclyl, Alkenyl, Alkylcarbonyl, Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl,  Alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl,
Alkoxycarbonyl, Hydroxycarbonyl, Cycloalkoxycarbonyl, Cycloalkylalkoxycarbonyl, Alkoxycarbonylalkyl, Arylalkoxycarbonyl, Arylalkoxycarbonylalkyl, Alkinyl, Alkinylalkyl, Alkylalkinyl, Tris-alkylsilylalkinyl, Nitro, Amino, Cyano, Haloalkoxy, Haloalkylthio, Alkylthio, Hydrothio, Hydroxyalkyl, Oxo, Heteroarylalkoxy, Arylalkoxy,  Alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trisalkylsilylalkynyl, nitro, amino, cyano, haloalkoxy, haloalkylthio, alkylthio, hydrothio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy,
Heterocyclylalkoxy, Heterocyclylalkylthio, Heterocyclyloxy, Heterocyclylthio,  Heterocyclylalkoxy, heterocyclylalkylthio, heterocyclyloxy, heterocyclylthio,
Heteroaryloxy, Bis-alkylamino, Alkylamino, Cycloalkylamino,  Heteroaryloxy, bis-alkylamino, alkylamino, cycloalkylamino,
Hydroxycarbonylaikylamino, Alkoxycarbonyiaikylamino, Arylalkoxycarbonylalkylamino, Alkoxycarbonylalkyl(alkyl)amino, Aminocarbonyl, Alkylaminocarbonyl, Bis- alkylaminocarbonyi, Cycloalkylaminocarbonyl, Hydroxycarbonylalkylaminocarbonyl, Alkoxycarbonylalkylaminocarbonyl, Arylalkoxycarbonylalkylaminocarbonyl substituiert.  Hydroxycarbonylaikylamino, Alkoxycarbonyiaikylamino, Arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl (alkyl) amino, aminocarbonyl, alkylaminocarbonyl, bis-alkylaminocarbonyi, cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl substituted.
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 main body is "substituted by one or more radicals" from an enumeration of radicals (= group) or a generically defined group of radicals, this includes the simultaneous substitution by several identical and / or structurally different radicals.
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 it is a partially or fully saturated nitrogen heterocycle, it may be linked to the rest of the molecule via both carbon and nitrogen.
Als Substituenten für einen substituierten heterocyclischen Rest kommen die weiter unten genannten Substituenten in Frage, zusätzlich auch Oxo und Thioxo. Die Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo. The
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(O)2 (auch kurz SO2) im heterocyclischen Ring. Im Fall von -N(O)- und -S(O)- Gruppen sind jeweils beide Enantiomere umfasst. Oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring. As a result, lactones and lactams are preferably also included. The oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. in the case of N and S, for example, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also SO2 for short) occur and form in the heterocyclic ring. In the case of -N (O) and -S (O) groups, both enantiomers are included.
Erfindungsgemäß steht der Ausdruck„Heteroaryl" für heteroaromatische According to the invention, the term "heteroaryl" is heteroaromatic
Verbindungen, d. h. vollständig ungesättigte aromatische heterocyclische Compounds, d. H. fully unsaturated aromatic heterocyclic
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. Compounds, preferably for 5- to 7-membered rings having 1 to 4, preferably 1 or 2 identical or different heteroatoms, preferably O, S or N.
Erfindungsgemäße Heteroaryle sind beispielsweise 1 H-Pyrroi-1 -yl; 1 H-Pyrrol-2-yl; 1 H- Pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1 H-lmidazol-1 -yl; 1 H- lmidazol-2-yl; 1 H-lmidazol-4-yl; 1 H-lmidazol-5-yl; 1 H-Pyrazol-1 -yl; 1 H-Pyrazol-3-yl; 1 H- Pyrazol-4-yl; 1 H-Pyrazol-5-yl, 1 H-1 ,2,3-Triazol-1 -yl, 1 H-1 ,2,3-Triazol-4-yl, 1 H-1 ,2,3- Triazol-5-yl, 2H-1 ,2,3-Triazol-2-yl, 2H-1 ,2,3-Triazol-4-yl, 1 H-1 ,2,4-Triazol-1-yl, 1 H- 1 ,2,4-Triazol-3-yl, 4H-1 ,2,4-Triazol-4-yl, 1 ,2,4-Oxadiazol-3-yl, 1 ,2,4-Oxadiazol-5-yl, 1 ,3,4-Oxadiazol-2-yl, 1 ,2,3-Oxadiazol-4-yl, 1 ,2,3-Oxadiazol-5-yl, 1 ,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, 1 ,3,5-Triazin-2-yl, 1 ,2,4- Triazin-3-yl, 1 ,2,4-Triazin-5-yl, 1 ,2,4-Triazin-6-yl, 1 ,2,3-Triazin-4-yl, 1 ,2,3-Triazin-5-yl, 1 ,2,4-, 1 ,3,2-, 1 ,3,6- und 1 ,2,6-Oxazinyl, lsoxazol-3-yl, lsoxazol-4-yl, lsoxazol-5-yl, 1 ,3- Oxazol-2-yl, 1 ,3-Oxazol-4-yl, 1 ,3-Oxazol-5-yl, lsothiazol-3-yl, lsothiazol-4-yl, Isothiazol- 5-yl, 1 ,3-Thiazol-2-yl, 1 ,3-Thiazol-4-yl, 1 ,3-Thiazol-5-yl, Oxepinyl, Thiepinyl, 1 ,2,4- Triazolonyl und 1 ,2,4-Diazepinyl, 2H-1 ,2,3,4-Tetrazol-5-yl, 1 H-1 ,2,3,4-Tetrazol-5-yl, 1 ,2,3,4-OxatriazoI-5-yl, 1 ,2,3,4-Thiatriazol-5-yl, 1 ,2,3,5-Oxatriazol-4-yS, 1 ,2,3,5- Thiatriazol-4-yl. Die erfindungsgemäßen Heteroarylgruppen können ferner mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. Sind zwei benachbarte Kohlenstoffatome Bestandteil eines weiteren aromatischen Rings, so handelt es sich um annellierte heteroaromatische Systeme, wie benzokondensierte oder mehrfach annellierte Heteroaromaten. 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. lsochinolin-1 -yl, lsochinolin-3-yl, lsochinolin-4-yl, lsochinolin-5-yl, lsochinolin-6-yl, lsochinolin-7-yl, lsochinolin-8-yl); Chinoxalin; Heteroaryls of the invention are, for example, 1H-pyrro-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazole-1-yl; 1 H-imidazol-2-yl; 1 H -imidazol-4-yl; 1 H -imidazol-5-yl; 1H-pyrazole-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1 H-pyrazol-5-yl, 1 H-1, 2,3-triazol-1-yl, 1 H-1, 2,3-triazol-4-yl, 1 H-1, 2,3-triazole 5-yl, 2H-1, 2,3-triazol-2-yl, 2H-1, 2,3-triazol-4-yl, 1H-1, 2,4-triazol-1-yl, 1H- 1, 2,4-triazol-3-yl, 4H-1, 2,4-triazol-4-yl, 1, 2,4-oxadiazol-3-yl, 1, 2,4-oxadiazol-5-yl, 1, 3,4-oxadiazol-2-yl, 1, 2,3-oxadiazol-4-yl, 1, 2,3-oxadiazol-5-yl, 1, 2,5-oxadiazol-3-yl, azepinyl, Pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazine-2-yl, pyrazine-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazine 3-yl, pyridazin-4-yl, 1, 3,5-triazin-2-yl, 1, 2,4-triazin-3-yl, 1, 2,4-triazin-5-yl, 1, 2, 4-triazin-6-yl, 1, 2,3-triazin-4-yl, 1, 2,3-triazin-5-yl, 1, 2,4-, 1, 3, 3, 1, 3, 6- and 1, 2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-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, 1, 3-thiazol-4-yl, 1, 3 Thiazol-5-yl, oxepinyl, thiepinyl, 1, 2,4- Triazolonyl and 1,2,4-diazepinyl, 2H-1,2,3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-5-yl, 1, 2,3,4 Oxatriazol-5-yl, 1,2,3,4-thiatriazol-5-yl, 1,2,3,5-oxatriazol-4-ys, 1,2,3,5-thiatriazol-4-yl. The heteroaryl groups according to the invention may furthermore be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics. Preference is given, for example, to quinolines (for example 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-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline;
Chinazolin; Cinnolin; 1 ,5-Naphthyridin; 1 ,6-Naphthyridin; 1 ,7-Naphthyridin; 1 ,8- Naphthyridin; 2,6-Naphthyridin; 2,7-Naphthyridin; Phthalazin; Pyridopyrazine; quinazoline; cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine;
Pyridopyrimidine; Pyridopyridazine; Pteridine; Pyrimidopyrimidine. Beispiele für Heteroaryl sind auch 5- oder 6-gliedrige benzokondensierte Ringe aus der Gruppe 1 H- lndol-1 -yl, 1 H-lndol-2-yl, 1 H-lndol-3-yl, 1 H-lndol-4-yl, 1 H-lndol-5-yl, 1 H-lndol-6-yl, 1 H- lndol-7-yl, 1 -Benzofuran-2-yl, 1 -Benzofuran-3-yl, 1-Benzofuran-4-yl, 1-Benzofuran-5-yl, 1 -Benzofuran-6-yl, 1 -Benzofuran-7-yl, 1 -Benzothiophen-2-yl, 1 -Benzothiophen-3-yl, 1 - Benzothiophen-4-yl, 1 -Benzothiophen-5-yl, 1 -Benzothiophen-6-yl, 1 -Benzothiophen-7- yl, 1 H-lndazol-1 -yl, 1 H-lndazol-3-yl, 1 H-lndazol-4-yl, 1 H-lndazol-5-yl, 1 H-lndazol-6-yl, 1 H-lndazol-7-yl, 2H-lndazol-2-yl, 2H-lndazol-3-yl, 2H-lndazol-4-yl, 2H-lndazol-5-yl, 2H- lndazol-6-yl, 2H-lndazol-7-yl, 2H-lsoindol-2-yl, 2H-lsoindol-1 -yl, 2H-lsoindol-3-yl, 2H- lsoindol-4-yl, 2H-lsoindol-5-yl, 2H-lsoindol-6-yl; 2H-lsoindol-7-yl, 1 H-Benzimidazol-1 -yl, 1 H-Benzimidazol-2-yl, 1 H-Benzimidazol-4-yl, 1 H-Benzimidazol-5-yl, 1 H-Benzimidazol- 6-yl, 1 H-Benzimidazol-7-yl, 1 ,3-Benzoxazol-2-yl, 1 ,3-Benzoxazol-4-yl, 1 ,3-Benzoxazol- 5-yl, 1 ,3-Benzoxazol-6-yl, 1 ,3-Benzoxazol-7-yl, 1 ,3-Benzthiazol-2-yl, 1 ,3-Benzthiazol-4- yl, 1 ,3-Benzthiazol-5-yl, 1 ,3-Benzthiazol-6-yl, 1 ,3-Benzthiazol-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, 1 ,2-Benzisothiazol-3-yl, 1 ,2-Benzisothiazol-4-yl, 1 ,2-Benzisothiazol- 5-yl, 1 ,2-Benzisothiazol-6-yl, 1 ,2-Benzisothiazol-7-yl. pyridopyrimidines; Pyridopyridazine; pteridines; Pyrimidopyrimidine. Examples of heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indole-4 yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4 -yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl , 1-benzothiophene-5-yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1-indazol-1-yl, 1-indazol-3-yl, 1-indazole-4-yl yl, 1H-indazol-5-yl, 1H-indazol-6-yl, 1H-indazol-7-yl, 2H-indazol-2-yl, 2H-indazol-3-yl, 2H-indazole-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-benzimidazole-6 -yl, 1H-benzimidazol-7-yl, 1, 3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazole-6 yl, 1,3-benzoxazol-7-yl, 1,3-benzthiazol-2-yl, 1,3-benzthiazol-4-yl, 1,3-benzthiazol-5-yl, 1,3-benzthiazole-6 yl, 1, 3-benzthiazol-7-yl, 1,2-benzisoxazol-3-yl, 1,2-benzisoxazol-4-yl, 1,2-benzisoxazol-5-yl, 1,2-benzisoxazole-6 yl, 1, 2-benzisoxazol-7-yl, 1,2-benzisothiazol-3-yl, 1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl, 1,2-benzisothiazole-6 yl, 1,2-benzisothiazol-7-yl.
Die Bezeichnung "Halogen" bedeutet beispielsweise Fluor, Chlor, Brom oder lod. Wird die Bezeichnung für einen Rest verwendet, dann bedeutet "Halogen" beispielsweise ein Fluor-, Chlor-, Brom- oder lodatom. Erfindungsgemäß bedeutet„Alky!" einen geradkettigen oder verzweigten offenkettigen, gesättigten Kohlen Wasserstoff rest, der gegebenenfalls ein- oder mehrfach substituiert, bevorzugt unsubstituiert ist. 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. The term "halogen" means, for example, fluorine, chlorine, bromine or iodine. When the term for a group is used, "halogen" means, for example, a fluorine, chlorine, bromine or iodine atom. According to the invention, "alky!" Denotes a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally mono- or polysubstituted, preferably unsubstituted, Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino- or nitro groups, particular preference is given to methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine.
„Haloalkyl", ,,-alkenyl" und ,,-alkinyl" bedeuten durch gleiche oder verschiedene "Haloalkyl", "- alkenyl" and "alkynyl" mean the same or different
Halogenatome, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. Monohaloalkyl (= Monohalogenalkyl) wie z. B. CH2CH2CI, CH2CH2Br, CHCICH3, CH2CI, CH2F; Perhaloalkyl wie z. B. CCh. CCIF2. CFCl2,CF2CCIF2. CF2CCIFCF3; Halogen atoms, partially or fully substituted alkyl, alkenyl or alkynyl, for example monohaloalkyl (= monohaloalkyl) such. CH 2 CH 2 Cl, CH 2 CH 2 Br, CHCICH3, CH 2 Cl, CH 2 F; Perhaloalkyl such. CCh. CCIF 2 . CFCl2, CF 2 CCIF second CF2CCIFCF3;
Polyhaloalkyl wie z. B. CH2CHFCI, CF2CCIFH, CF2CBrFH, CH2CF3; Der Begriff Perhaloalkyl umfasst dabei auch den Begriff Perfluoralkyl. Polyhaloalkyl such. B. CH2CHFCI, CF2CCIFH, CF 2 CBrFH, CH2CF3; The term perhaloalkyl also encompasses the term perfluoroalkyl.
Teilfluoriertes Alkyl bedeutet einen geradkettigen oder verzweigten, gesättigten Partially fluorinated alkyl means a straight-chain or branched, saturated
Kohlenwasserstoff, der einfach oder mehrfach durch Fluor substituiert ist, wobei sich die entsprechenden Fluoratome als Substituenten an einem oder mehreren Hydrocarbon which is mono- or polysubstituted by fluorine, wherein the corresponding fluorine atoms as substituents on one or more
verschiedenen Kohlenstoffatomen der geradkettigen oder verzweigten different carbon atoms of the straight-chain or branched
Kohlenwasserstoffkette befinden können, wie z. B. CHFCH3, CH2CH2F, CH2CH2CF3, CHF2, CH2F, CHFCF2CF3 Hydrocarbon chain can be located, such as. B. CHFCH3, CH2CH2F, CH2CH2CF3, CHF 2, CH 2 F, CHFCF2CF3
Teilfluoriertes Haloalkyl bedeutet einen geradkettigen oder verzweigten, gesättigten Kohlenwasserstoff, der durch verschiedenene Halogenatomen mit mindestens einem Fluoratom substituiert ist, wobei alle anderen gegebenenfalls vorhandenen Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, all other optionally present
Halogenatome ausgewählt sind aus der Gruppe Fluor, Chlor oder Brom, lod. Die entsprechenden Halogenatome können sich dabei als Substituenten an einem oder mehreren verschiedenen Kohlenstoffatomen der geradkettigen oder verzweigten Kohlenwasserstoffkette befinden. Teilfluoriertes Haloalkyl schließt auch die Halogen atoms are selected from the group fluorine, chlorine or bromine, iodine. The corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain. Partially fluorinated haloalkyl also includes the
vollständige Substitution der geradkettigen oder verzweigten Kette durch Halogen unter Beteiligung von mindestens einem Fluoratom ein. complete substitution of the straight-chain or branched chain by halogen with the participation of at least one fluorine atom.
Haloalkoxy ist z.B. OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 und OCH2CH2CI; Haloalkoxy is eg OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl;
Entsprechendes gilt für Haloalkenyl und andere durch Halogen substituierten Reste. 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 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-C-6)-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. The term "(C 1 -C 4) -alkyl" given here by way of example means a A shorthand notation for straight-chain or branched alkyl having one to 4 carbon atoms corresponding to the range for C atoms, ie, the radicals comprises methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl , General alkyl radicals having a larger specified range of carbon atoms, eg. B. "(Ci-C-6) -alkyl", accordingly also include straight-chain or branched alkyl radicals having a larger number of carbon atoms, ie according to Example, the alkyl radicals having 5 and 6 carbon atoms.
Wenn nicht speziell angegeben, sind bei den Kohlenwasserstoff resten wie Alkyl-, Alkenyl- und Alkinylresten, auch in zusammengesetzten Resten, die niederen Unless specifically stated, in the hydrocarbon radicals such as alkyl, alkenyl and alkynyl, even in assembled radicals, are the lower
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 1 ,3-Dimethylbutyl, Heptyle, wie n-Heptyl, 1-Methylhexyl und 1 ,4-Dimethylpentyl; Alkenyl- und Alkinylreste haben die Bedeutung der den Aikylresten entsprechenden möglichen ungesättigten Reste, wobei mindestens eine Doppelbindung bzw. Dreifachbindung enthalten ist. Bevorzugt sind Reste mit einer Doppelbindung bzw. Dreifachbindung. Der Begriff„Alkenyl" schließt insbesondere auch geradkettige oder verzweigte offenkettige Kohlen Wasserstoff reste mit mehr als einer Doppelbindung ein, wie 1 ,3- Butadienyl und 1 ,4-Pentadienyl, aber auch Allenyl- oder Kumulenyl-reste mit einer bzw. mehreren kumulierten Doppelbindungen, wie beispielsweise Allenyl (1 ,2- Propadienyl), 1 ,2-Butadienyl und 1 ,2,3-Pentatrienyl. Alkenyl bedeutet z.B. Vinyl, welches ggf. durch weitere Alkylreste substituiert sein kann, z.B. Prop-1 -en-1-yl, But-1- en-1 -yl, Allyl, 1 -Methyl-prop-2-en-1 -yl, 2-Methyl-prop-2-en-1 -yl, But-2-en-1-yl, 1 - Methyl-but-3-en-1 -yl und 1 -Methyl-but-2-en-1 -yl, 2-Methyl-prop-1 -en-1 -yl,  Carbon skeletons, e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, preferred. Alkyl radicals, also in the assembled 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 Aikylresten, wherein at least one double bond or triple bond is included. Preference is given to radicals having a double bond or triple bond. The term "alkenyl" also includes in particular straight-chain or branched open-chain carbon hydrogen radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds alkenyl is, for example, vinyl, which may optionally be substituted by further alkyl radicals, for example propylene-1-ene-1, such as, for example, allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl. yl, but-1-en-1-yl, allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-ene-1 yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl, 2-methyl-prop-1 -ene-1-yl,
1 -Methylprop-1 -en-1 -yl, 1 -Methylprop-2-en-1 -yl, 2-Methyl-prop-2-en-1 -yl, But-2-en-1 -yl, But-3-en-1 -yl, 1-Methyl-but-3-en-1-yl oder 1 -Methyl-but-2-en-1 -yl, Pentenyl, 1-methylprop-1 -en-1-yl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, butyrene 3-en-1-yl, 1-methyl-but-3-en-1-yl or 1-methylbut-2-en-1-yl, pentenyl,
2-Methylpentenyl oder Hexenyl. 2-methylpentenyl or hexenyl.
Der Begriff„Alkinyl" schließt insbesondere auch geradkettige oder verzweigte offenkettige Kohlenwasserstoff reste mit mehr als einer Dreifachbindung oder auch mit einer oder mehreren Dreifachbindungen und einer oder mehreren Doppelbindungen ein, wie beispielsweise 1 ,3-Butatrienyl bzw. 3-Penten-1 -in-1 -yl. (C2-C6)-Alkinyl bedeutet beispielsweise Ethinyl, Propargyl, 1 - ethyl-prop-2-in-1 -yl, 2-Butinyl, The term "alkynyl" in particular also includes straight-chain or branched open-chain hydrocarbon radicals having more than one triple bond or else having one or more triple bonds and one or more double bonds such as 1,3-butatrienyl and 3-penten-1-yn-1-yl, respectively. (C 2 -C 6) -alkynyl is, for example, ethynyl, propargyl, 1-ethyl-prop-2-yn-1-yl, 2-butynyl,
2-Pentinyl oder 2-Hexinyl, vorzugsweise Propargyl, But-2-in-1-yl, But-3-in-1-yl oder 1 - ethyl-but-3-in-1 -yl. 2-pentynyl or 2-hexynyl, preferably propargyl, but-2-yn-1-yl, but-3-yn-1-yl or 1-ethyl-but-3-yn-1-yl.
Der Begriff„Cycloalkyl" bedeutet ein carbocyciisches, gesättigtes Ringsystem mit vorzugsweise 3-8 Ring-C-Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl. Im Falle von gegebenenfalls substituiertem Cycloalkyl werden cyclische Systeme mit Substituenten umfasst, wobei auch Substituenten mit einer The term "cycloalkyl" means a carbocyclic saturated ring system preferably having 3-8 ring C atoms, e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. In the case of optionally substituted cycloalkyl, cyclic systems having substituents are also contemplated wherein substituents also have one
Doppelbindung am Cycloalkylrest, z. B. eine Alkylidengruppe wie Methyliden, umfasst sind. Im Falle von gegebenenfalls substituiertem Cycloalkyl werden auch Double bond on the cycloalkyl, z. As an alkylidene group such as methylidene, are included. In the case of optionally substituted cycloalkyl also become
mehrcyclische aliphatische Systeme umfaßt, wie beispielsweise Bicyclo[ .1 .0]butan-1 - yl, Bicyclo[1 .1 .0]butan-2-yl, Bicyclo[2.1 .0]pentan-1 -yl, Bicyclo[2.1.0]pentan-2-yl, Bicyclo[2.1 .0]pentan-5-yl, Bicyclo[2.2.1]hept-2-yl (Norbornyl), Bicyclo[2.2.2]octan-2-yl, Adamantan-1 -yl und Adamantan-2-yl. Der Ausdruck "(C3-C7)-Cycloalkyl" bedeutet eine Kurzschreibweise für Cycloalkyl mit drei bis 7 Kohlenstoffatomen entsprechend der Bereichsangabe für C-Atome. polycyclic aliphatic systems such as, for example, bicyclo [.1] o-butan-1-yl, bicyclo [1 .1] -butan-2-yl, bicyclo [2.1.0] pentan-1-yl, bicyclo [2.1. 0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.2.1] hept-2-yl (norbornyl), bicyclo [2.2.2] octan-2-yl, adamantane-1 -yl and adamantan-2-yl. The term "(C3-C7) cycloalkyl" means a shorthand notation for cycloalkyl having from three to seven carbon atoms corresponding to the range of C atoms.
Im Falle von substituiertem Cycloalkyl werden auch spirocyclische aliphatische In the case of substituted cycloalkyl are also spirocyclic aliphatic
Systeme umfaßt, wie beispielsweise Spiro[2.2]pent-1-yl, Spiro[2.3]hex-1 -yl, Systems such as spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl,
Spiro[2.3]hex-4-yl, 3-Spiro[2.3]hex-5-yl. Spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl.
„Cycloalkenyl" bedeutet ein carbocyciisches, 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-"Cycloalkenyl" means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-
Cyclohexenyl, 3-Cyclohexenyl, 1 ,3-Cyclohexadienyl oder 1 ,4-Cyclohexadienyl, wobei auch Substituenten mit einer Doppelbindung am Cycloalkenylrest, z. B. eine Cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl, wherein also substituents having a double bond on the cycloalkenyl, z. Legs
Alkylidengruppe wie Methyliden, umfasst sind. Im Falle von gegebenenfalls Alkylidene group such as methylidene, are included. In case of if necessary
substituiertem Cycloalkenyl gelten die Erläuterungen für substituiertes Cycloalkyl entsprechend. Substituted cycloalkenyl the explanations for substituted cycloalkyl apply accordingly.
Der Begriff„Alkyliden", z. B. auch in der Form (C-i-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. =CH2, =CH-CH3, The term "alkylidene", for example also in the form of (C 1 -C 10) -alkylidene, means the radical of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond naturally only positions on the body in question, where two H atoms can be replaced by the double bond; Remains are z. B. = CH 2, = CH-CH 3,
=C(CH3)-CH3, =C(CH3)-C2H5 oder Cycloalkyliden bedeutet ein carbocyclischer Rest, der über eine Zweifachbindung gebunden ist. = C (CH 3 ) -CH 3 , = C (CH 3 ) -C 2 H 5 or Cycloalkylidene means a carbocyclic radical which is bonded via a double bond.
Der Begriff„Stannyl" steht für einen weiter substituierten Rest, der ein Zinn-Atom enthält;„Germanyl" steht analog für einen weiter substituierten Rest, der ein The term "stannyl" stands for a further substituted radical containing a tin atom, "Germanyl" is analogous to a further substituted radical which is a
Germanium-Atom enthält.„Zirconyl" steht für einen weiter substituierten Rest, der ein Zirconium-Atom enthält.„Hafnyl" steht für einen weiter substituierten Rest, der ein Hafnium-Atom enthält.„Boryl",„Borolanyl" und„Borinanyl" steht für weiter substituierte und gegebenenfalls cyclische Gruppen, die jeweils ein Bor-Atom enthalten. "Zirconyl" represents a further substituted radical containing a zirconium atom. "Hafnyl" represents a further substituted radical containing a hafnium atom. "Boryl", "Borolanyl" and "Borinanyl". is further substituted and optionally cyclic groups, each containing a boron atom.
„Plumbanyl" steht für einen weiter substituierten Rest, der ein Blei-Atom enthält. "Plumbanyl" represents a further substituted radical containing a lead atom.
„Hydrargyl" steht für einen weiter substituierten Rest, der ein Quecksilber-Atom enthält. „Alanyl" steht für einen weiter substituierten Rest, der ein Aluminium-Atom enthält. „Magnesyl" steht für einen weiter substituierten Rest, der ein Magnesium-Atom enthält. „Zinkyl" steht für einen weiter substituierten Rest, der ein Zink-Atom enthält. "Hydrargyl" represents a further substituted radical containing a mercury atom. "Alanyl" represents a further substituted radical containing an aluminum atom. "Magnesyl" represents a further substituted radical containing a magnesium atom. "Zincyl" represents a further substituted radical containing a zinc atom.
Die Verbindungen der allgemeinen Formel (I) 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- Isomere sind alle von der Formel (I) umfasst. Sind beispielsweise eine oder mehrere Alkenylgruppen vorhanden, so können Diastereomere (Z- und E-Isomere) auftreten. Sind beispielsweise ein oder mehrere asymmetrische Kohlenstoffatome vorhanden, so können Enantiomere und Diastereomere auftreten. Stereoisomere lassen sich aus den bei der Herstellung anfallenden Gemischen nach üblichen Trennmethoden erhalten. Die chromatographische Trennung kann sowohl im analytischen Maßstab zur Depending on the nature and linkage of the substituents, the compounds of the general formula (I) can exist as stereoisomers. The possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Stereoisomers can be obtained from the resulting mixtures in the preparation by conventional separation methods. The chromatographic separation can be used both on an analytical scale for
Feststellung des Enantiomerenüberschusses bzw. des Diastereomerenüberschusses, wie auch im präparativen Maßstab zur Herstellung von Prüfmustern für die biologische Ausprüfung 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 (I) umfasst, jedoch nicht mit ihrer spezifischen Stereoform angegeben sind, sowie deren Gemische Synthese: Determination of the enantiomeric excess or of the diastereomeric excess, as also carried out on a preparative scale for the production of test samples for biological testing. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants. The invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof Synthesis:
Substituierte 2-Amidobenzimidazole können nach bekannten Verfahren hergestellt werden (vgl. J. Med. Chem. 2000, 43, 4084; Bioorg. Med. Chem. 2008, 16, 6965; Bioorg. Med. Chem. 2008, 16, 3955; Org. Proc. Res. Develop. 2007, 1 1 , 693; J. Med. Chem. 2009, 52, 514; J. Heterocyclic Chem. 2001 , 38, 979; WO2000026192; Substituted 2-amidobenzimidazoles can be prepared by known methods (compare J. Med. Chem. 2000, 43, 4084, Bioorg. Med. Chem. 2008, 16, 6965, Bioorg. Med. Chem. 2008, 16, 3955; Org Proc. Res. Develop., 2007, 11, 693; J. Med. Chem. 2009, 52, 514; J. Heterocyclic Chem. 2001, 38, 979; WO2000026192;
WO2003106430; WO9704771 ; WO2000029384, WO2000032579). Verschiedene literaturbekannte Herstellungswege zum Aufbau der Kernstruktur wurden verwendet und teilweise optimiert (siehe Schema 1 ). Ausgewählte detaillierte Synthesebeispiele sind im nächsten Abschnitt aufgeführt. Die eingesetzten und untersuchten WO2003106430; WO9704771; WO2000029384, WO2000032579). Various manufacturing routes known to build the core structure were used and partially optimized (see Scheme 1). Selected detailed synthesis examples are listed in the next section. The used and examined
Syntheserouten gehen dabei von kommerziell erhältlichen oder leicht herstellbaren 2- Amino-3-nitrobenzoesäuren oder 2,3-Diaminobenzonitrilen aus. Die betreffende gegebenenfalls zusätzlich substituierte 2-Amino-3-nitrobenzoesäure kann mit Hilfe von Thionylchlorid und Ammoniak in das entsprechende 2-Amino-3-nitrobenzamid überführt werden, das entweder mit Wasserstoff in Gegenwart von Palladium auf Kohle in einem geeigneten Lösungsmittel oder mit Zinn(ll)chlorid in zu einem gegebenenfalls weiter substituierten 2,3-Diaminobenzamid reduziert wird. Das so erhaltene 2,3-Diaminobenzamid kann im folgenden Schritt über verschiedene  Synthetic routes are based on commercially available or easily prepared 2-amino-3-nitrobenzoic acids or 2,3-diaminobenzonitriles. The optionally additionally substituted 2-amino-3-nitrobenzoic acid in question can be converted with the aid of thionyl chloride and ammonia into the corresponding 2-amino-3-nitrobenzamide, either with hydrogen in the presence of palladium on carbon in a suitable solvent or with tin ( ll) chloride is reduced to an optionally further substituted 2,3-diaminobenzamide. The thus obtained 2,3-diaminobenzamide can in the following step on various
Reaktionsvarianten, z. B. Kondensation mit einer Carbonsäure, mit einem Aldehyd oder einem Amidoxim, in das gewünschte Benzimidazolderivat überführt werden.Reaction variants, eg. For example, condensation with a carboxylic acid, with an aldehyde or an amidoxime can be converted into the desired benzimidazole derivative.
Alternativ kann das entsprechende Benzimidazol auch durch Kondensation einer 2,3- Diaminobenzoesäure mit einer Carbonsäure oder durch N-Acylierung eines 2-Amino- 3-nitrobenzoesäureesters und nachfolgende Reduktion mit Wasserstoff in Gegenwart von Palladium auf Kohle aufgebaut und die Carboxylfunktion im abschließenden Schritt in das gewünschte Amid überführt werden. Einen weiteren Reaktionsweg zur Synthese der erfindungsgemäßen Verbindungen stellt die Kondensation eines gegebenenfalls substituierten 2,3-Diaminobenzonitrils mit einer entsprechenden Carbonsäure und die nachfolgende Umsetzung mit einer Hydroxidbase (z. B. Alternatively, the corresponding benzimidazole can also be constructed by condensation of a 2,3-diaminobenzoic acid with a carboxylic acid or by N-acylation of a 2-amino-3-nitrobenzoic acid ester and subsequent reduction with hydrogen in the presence of palladium on carbon and the carboxyl function in the final step in the desired amide be transferred. A further reaction route for the synthesis of the compounds according to the invention is the condensation of an optionally substituted 2,3-diaminobenzonitrile with a corresponding carboxylic acid and the subsequent reaction with a hydroxide base (eg.
Kaliumhydroxid) in einem protischen Lösungsmittel (z.B. Ethanol) dar. Die im folgenden Schema 1 genannten Reste R1, R2, R3 und Q haben die zuvor definierten Bedeutungen. Potassium hydroxide) in a protic solvent (eg ethanol). The radicals R 1 , R 2 , R 3 and Q mentioned in the following scheme 1 have the meanings defined above.
Die erhaltenen carboxyl-substituierten Benzimidazole können mit Hilfe von The resulting carboxyl-substituted benzimidazoles can be obtained with the aid of
Thionylchlorid in einem geeigneten Lösungsmittel und nachfolgender Umsetzung mit einem substituierten Amin oder einem substituierten Sulfonamid in entsprechend N- substituierte Benzimidazole überführt werden. Die Funktionalisierung eines Thionyl chloride in a suitable solvent and subsequent reaction with a substituted amine or a substituted sulfonamide are converted into corresponding N-substituted benzimidazoles. The functionalization of a
Benzimidazol-N-Atoms gelingt durch Deprotonierung mit einer geeigneten Base, z. B. Natriumhydrid in einem aprotischen Lösungsmittel, und nachfolgende Umsetzung mit einem geeigneten Elektrophil, z.B. einem Acylchlorid, einem Alkylhalogenid oder einem Chloroformat. Die Amidgruppe der erfindungsmäßig hergestellten Fluoralkyl- substituierten 2-Amidobenzimidazole kann außerdem in das entsprechende Thioamid mit Hilfe von 2,4-Bis-(4-methoxyphenyl)-1 , 3,2,4- dithiadiphosphetan-2,4-disulfid oder in einer zweistufigen Synthese durch Reaktion mit tert.-Butylhypochlorit und AIBN in einem aprotischen Lösungsmittel (z. B. Benzimidazole N-atom succeeds by deprotonation with a suitable base, for. For example, sodium hydride in an aprotic solvent, and subsequent reaction with a suitable electrophile, for example an acyl chloride, an alkyl halide or a chloroformate. The amide group of the fluoroalkyl-substituted 2-amidobenzimidazoles prepared according to the invention can also be converted into the corresponding thioamide with the aid of 2,4-bis- (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane-2,4-disulfide or in a two-step synthesis by reaction with tert-butyl hypochlorite and AIBN in an aprotic solvent (e.g. B.
Tetrachlorkohlenstoff) und nachfolgende Umsetzung mit einem Dialkylsulfid in Carbon tetrachloride) and subsequent reaction with a dialkyl sulfide in
Gegenwart einer Base (z. B. Triethylamin) in einem geeigneten Lösungsmittel (z. B. Toluol) in die entsprechenden substituierten Sulfilimine überführt werden (siehe Schema 2). Die im folgenden Schema 2 aufgeführten Reste R\ R2, R3 und Q haben die zuvor definierten Bedeutungen, zusätzlich werden in Schema 2 beispielhaft die Substituenten Methyl, Ethyl und iso-Propyl als Stellvertreter für die Presence of a base (eg, triethylamine) in a suitable solvent (eg, toluene) into the corresponding substituted sulfilimines (see Scheme 2). The radicals R 1 , R 3 and Q listed in the following scheme 2 have the meanings defined above; in addition, in Scheme 2, the substituents methyl, ethyl and isopropyl are used as representatives for the compounds
erfindungsgemäßen Gruppen dargestellt. Die Herstellung und Verwendung der erfindungsgemäßen Verbindungen geht aus den nachfolgenden Beispielen hervor. represented groups of the invention. The preparation and use of the compounds according to the invention are evident from the examples below.
Schema 2.  Scheme 2.
Substituierte 2-Amidobenzoxazole können ebenfalls nach bekannten Verfahren hergestellt werden (vgl. Bioorg. Med. Chem. 2006, 14, 6106; WO2010083220; Substituted 2-amidobenzoxazoles can likewise be prepared by known processes (compare, Bioorg.Med.Chem., 2006, 14, 6106, WO2010083220;
US20090197863; W09524379). Die eingesetzten und untersuchten Syntheserouten gehen dabei von kommerziell erhältlichen oder leicht herstellbaren 2-Amino-3- hydroxybenzoesäuren oder ihren analogen Estern aus (Schema 3). In Schema 3 wird die Synthesesequenz beispielhaft unter Verwendung eines Ethylesters gezeigt, ohne die erfindungsgemäße Restedefinition einzuschränken. Der betreffende US20090197863; W09524379). The used and examined synthesis routes are based on commercially available or easily prepared 2-amino-3-hydroxybenzoic acids or their analogous esters (Scheme 3). In Scheme 3, the synthetic sequence is exemplified using an ethyl ester without limiting the definition of the invention. The concerned
gegebenenfalls weiter substituierte 2-Amino-3-hydroxybenzoesäureethylester wird dabei mit einem geeigneten Anhydrid in THF oder durch Kondensation mit einer geeigneten Carbonsäure in das entsprechende gegebenenfalls weiter substituierte Benzoxazol überführt. Im folgenden Schritt wird der Ethylester mit Hilfe einer geeigneten Hydroxidbase gespalten (z. B. LiOH, KOH oder NaOH) und man erhält die gegebenenfalls weiter substituierte Benzoxazolylcarbonsäure, die danach durch Verwendung von Thionylchlorid und folgende Umsetzung des Säurechlorids mit Ammoniak in das erfindungsgemäße gegebenenfalls weiter substituierte 2- Amidobenzoxazol überführt wird. Die im folgenden Schema 3 genannten Reste R\ R2, R3 und Q haben die zuvor definierten Bedeutungen. optionally further substituted 2-amino-3-hydroxybenzoesäureethylester is thereby converted with a suitable anhydride in THF or by condensation with a suitable carboxylic acid in the corresponding optionally substituted benzoxazole. In the following step, the ethyl ester is cleaved with the aid of a suitable hydroxide base (for example LiOH, KOH or NaOH) to give the optionally further substituted benzoxazolylcarboxylic acid, which may then be further introduced into the product according to the invention by using thionyl chloride and subsequent reaction of the acid chloride with ammonia substituted 2-amidobenzoxazole is transferred. The radicals R 1 , R 3 and Q mentioned in the following scheme 3 have the meanings defined above.
Substituierte 2-Amidobenzothiazole können in Analogie zu den oben beschriebenen Synthesewegen ebenfalls nach literaturbekannten Verfahren hergestellt werden (vgl. Bioorg. Med. Chem. 2006, 14, 6106; WO2010083199). Dabei werden gegebenenfalls weiter substituierte 2-Nitro-3-chlorbenzoesäuren zuerst mit Hilfe von Natriumsulfid- Hydrat in einem geeigneten polar-protischen Lösungsmittel (z. B. Methanol oder Wasser) in die entsprechenden 2-Amino-3-Hydrothiobenzoesäuren überführt (Schema 4). Die betreffende gegebenenfalls weiter substituierte 2-Amino-3- hydrothiobenzoesäure wird dabei mit einem geeigneten Anhydrid in THF oder durch direkte Kondensation mit einer geeigneten Carbonsäure in die entsprechende gegebenenfalls weiter substituierte Benzothiazolylcarbonsäure überführt, die danach durch Verwendung von Thionylchlorid oder einem anderen geeigneten Substituted 2-amidobenzothiazoles can likewise be prepared analogously to the synthesis routes described above by processes known from the literature (compare Bioorg.Med.Chem. 2006, 14, 6106, WO2010083199). Optionally, further substituted 2-nitro-3-chlorobenzoic acids are first converted into the corresponding 2-amino-3-hydrothiobenzoic acids with the aid of sodium sulfide hydrate in a suitable polar protic solvent (eg methanol or water) (Scheme 4). , The relevant optionally further substituted 2-amino-3-hydrothiobenzoic acid is in this case with a suitable anhydride in THF or by direct condensation with a suitable carboxylic acid in the corresponding optionally further substituted benzothiazolylcarboxylic acid, which is subsequently purified by use of thionyl chloride or another suitable
Chlorierungsreagenz (z. B. Oxalylchlorid) und folgende Umsetzung des Säurechlorids mit Ammoniak zu dem erfindungsgemäßen gegebenenfalls weiter substituierten 2- Amidobenzothiazol umgesetzt wird. Die im folgenden Schema 4 genannten Reste R\ R2, R3 und Q haben ebenfalls die zuvor definierten Bedeutungen. Chlorination reagent (eg., Oxalylchlorid) and subsequent reaction of the acid chloride with ammonia to the optionally further substituted 2-amidobenzothiazole according to the invention is reacted. The radicals R 1 , R 3 and Q mentioned in the following scheme 4 likewise have the meanings defined above.
Die 1H-NMR-, 13C-NMR- und 19F-NMR-spektroskopischen Daten, die für die in den nachfolgenden Abschnitten beschriebenen chemischen Beispiele angegeben sind, (400 MHz bei 1H-NMR und 150 MHz bei 13C-NMR und 375 MHz bei 19F-NMR, The 1 H NMR, 13 C NMR and 19 F NMR spectroscopic data reported for the chemical examples described in the following sections (400 MHz for 1 H NMR and 150 MHz for 13 C NMR and 375 MHz at 19 F NMR,
Lösungsmittel CDC , CD3OD oder de-DMSO, interner Standard: Tetrametylsilan δ = 0.00 ppm), wurden mit einem Gerät der Firma Bruker 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 =  Solvents CDC, CD3OD or de-DMSO, internal standard: tetramethylsilane δ = 0.00 ppm), were obtained with a Bruker instrument and the indicated signals have the following meanings: br = broad (es); s = singlet, d = doublet, t = triplet, dd = double doublet, ddd = doublet of double doublet, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq =
Doppelquartett, dt = Doppeltriplett, tt = Trippeltriplett Synthesebeispiele: Double quartet, dt = double triplet, tt = triple triplet Synthesis Examples:
No. A1 -13: 2-(4-Brom-3-Fluorphenyl)- ,3-benzimidazol-4-carboxamid No. A1 -13: 2- (4-bromo-3-fluorophenyl) -, 3-benzimidazole-4-carboxamide
2-Amino-3-nitrobenzoesäuremethylester (1.30 g, 6.63 mmol) wurde in abs. THF (Tetrahydrofuran) (10 ml) gelöst, mit Triethylamin (2.77 ml, 19.88 mmol) versetzt und 20 min lang unter Argon bei Raumtemperatur gerührt. Danach wurde langsam tropfenweise eine Lösung von 3-Fluoro-4-brombenzoesäurechlorid (19.88 mmol) in abs. THF (5 ml) zugegeben und das Reaktionsgemisch 4 h lang bei Raumtemperatur nachgerührt. Nach der Zugabe von Wasser wurde die wässrige Phase mehrfach mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden danach nochmals mit Wasser extrahiert, über Magnesiumsulfat getrocknet, abfiltriert und eingeengt. Durch säulenchromatographische Reinigung des resultierenden Rohproduktes konnte Methyl-2-amino-3-[(4-brom-3-fluorbenzoyl)amino]benzoat isoliert werden. Methyl-2- amino-3-[(4-brom-3-fluorbenzoyl)amino]benzoat (5.26 mmol) wurde danach in Methyl 2-amino-3-nitrobenzoate (1.30 g, 6.63 mmol) was dissolved in abs. THF (tetrahydrofuran) (10 ml), added triethylamine (2.77 ml, 19.88 mmol) and stirred at room temperature for 20 minutes under argon. Thereafter, slowly a dropwise solution of 3-fluoro-4-bromobenzoesäurechlorid (19.88 mmol) in abs. THF (5 ml) was added and the reaction mixture stirred for 4 h at room temperature. After the addition of water, the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were then extracted again with water, dried over magnesium sulfate, filtered off and concentrated. By column chromatographic purification of the resulting crude product, methyl 2-amino-3 - [(4-bromo-3-fluorobenzoyl) amino] benzoate was isolated. Methyl 2-amino-3 - [(4-bromo-3-fluorobenzoyl) amino] benzoate (5.26 mmol) was then added in
Methanol (50 ml) gelöst und in einem Metallgefäß zu Palladium auf Kohle  Dissolved methanol (50 ml) and in a metal vessel to palladium on carbon
(wassernasser Katalysator, 10%ig, 0.02 equiv, 84 mg, 0.079 mmol) in Methanol (30 ml) gegeben. In einem Laborreaktor wurde Wasserstoff in das Metallgefäß eingeleitet und das resultierende Reaktionsgemisch 5 h lang bei einem Druck von 2 bar bei Raumtemperatur gerührt. Nach vollständigem Umsatz wurde der Katalysator über Celite abfiltriert und mit Methanol nachgewaschen. Vom Filtrat wird das Lösungsmittel unter vermindertem Druck sorgfältig abdestilliert und der Rückstand säulen- chromatographisch (Kieselgel, Gradient mit n-Heptan und Essigester) gereinigt. Man erhielt Methyl-2-(4-brom-3-fluorphenyl)-1 H-benzimidazol-4-carboxylat (49 % der Theorie), das im nächsten Schritt in THF (1 ml) angelöst und mit Wasser (7 ml) sowie Natriumhydroxid (163 mg, 4.08 mmol) versetzt wurde. Das entstandene Reaktionsgemisch wurde 3 h lang unter Rückfluß gerührt. Nach dem Abkühlen auf Raumtemperatur wurde ein pH-Wert von 2-3 durch Zugabe von verd. HCl eingestellt und der entstandene Niederschlag abgesaugt, mit Heptan nachgewaschen sowie getrocknet. Auf diese Weise konnte 2-(4-Brom-3-fluorphenyl)-1 H-benzimidazol-4- carbonsäure (75 % der Theorie) erhalten werden, die dann in Dichlormethan (6 ml) gelöst und mit Oxalsäuredichlorid (1 .73 mmol) sowie einer katalytischen Menge N,N- Dimethylformamid versetzt wurde. Das Reaktionsgemisch wurde 15 min lang bei Raumtemperatur und danach 2 h lang bei 70 °C gerührt und im Anschluß komplett eingeengt. Nach Zugabe von Toluol wurde erneut eingeengt und das so erhaltene Säurechlorid ohne weitere Aufreinigung in Dioxan (6 ml) gelöst. Dann wurde unter(water-wet catalyst, 10%, 0.02 equiv, 84 mg, 0.079 mmol) in methanol (30 ml). In a laboratory reactor, hydrogen was introduced into the metal vessel and the resulting reaction mixture was stirred for 5 hours at a pressure of 2 bar at room temperature. After complete conversion, the catalyst was filtered through Celite and washed with methanol. From the filtrate, the solvent is carefully distilled off under reduced pressure and the residue purified by column chromatography (silica gel, gradient with n-heptane and ethyl acetate). This gave methyl 2- (4-bromo-3-fluorophenyl) -1H-benzimidazole-4-carboxylate (49% of theory), which in the next step dissolved in THF (1 ml) and with water (7 ml) and Sodium hydroxide (163 mg, 4.08 mmol) was added. The resulting The reaction mixture was stirred at reflux for 3 hours. After cooling to room temperature, a pH of 2-3 was adjusted by adding dil. HCl and the resulting precipitate was filtered off with suction, washed with heptane and dried. In this way, 2- (4-bromo-3-fluorophenyl) -1H-benzimidazole-4-carboxylic acid (75% of theory) was obtained, which was then dissolved in dichloromethane (6 ml) and treated with oxalic acid dichloride (1.73 mmol ) and a catalytic amount of N, N-dimethylformamide was added. The reaction mixture was stirred for 15 minutes at room temperature and then for 2 hours at 70 ° C and then concentrated completely. After addition of toluene was concentrated again and the acid chloride thus obtained without further purification in dioxane (6 ml). Then it was under
Kühlung Ammoniak (g) eingeleitet und 1 h lang bei Raumtemperatur nachgerührt. Das Reaktionsgemisch wurde vollständig eingeengt und der Rückstand säulen- chromatographisch (Kieselgel, Gradient mit n-Heptan und Essigester) gereinigt. Man erhielt 2-(4-Brom-3-Fluorphenyl)-1 ,3-benzimidazol-4-carboxamid (620 mg, 81 % der Theorie). 1H-NMR (400 MHz, de-DMSO δ, ppm) 13.55 (s, 1 H, NH), 9.23 (s, 1 H, NH), 8.25 (d, 1 H), 8.05 (d, 1 H), 7.90 (m, 2H), 7.75 (m, 2H), 7.41 (t, 1 H). Cooling ammonia (g) introduced and stirred for 1 h at room temperature. The reaction mixture was completely concentrated and the residue was purified by column chromatography (silica gel, gradient with n-heptane and ethyl acetate). 2- (4-Bromo-3-fluorophenyl) -1,3-benzimidazole-4-carboxamide (620 mg, 81% of theory) was obtained. 1 H-NMR (400 MHz, de-DMSO δ, ppm) 13.55 (s, 1H, NH), 9.23 (s, 1H, NH), 8.25 (d, 1H), 8.05 (d, 1H) , 7.90 (m, 2H), 7.75 (m, 2H), 7.41 (t, 1H).
No. A1 -181 : tert-Butyl-4-(4-carbamoyl-1 H-benzimidazol-2-yl)piperidin-1-carboxylat No. A1 -181: tert -Butyl 4- (4-carbamoyl-1H-benzimidazol-2-yl) piperidine-1-carboxylate
2,3-Diaminobenzamid (500 mg, 3.30 mmol) und 1 -A/-Boc-4-Piperidincarboxaldehyd (776 mg, 3.63 mmol) wurden bei Raumtemperatur in DMA (Dimethylamid) vorgelegt. Unter intensivem Rühren wurde die Reaktionslösung bei Raumtemperatur mit 2,3-Diaminobenzamide (500 mg, 3.30 mmol) and 1 -A / -Boc-4-piperidinecarboxaldehyde (776 mg, 3.63 mmol) were initially charged at room temperature in DMA (dimethylamide). With intensive stirring, the reaction solution at room temperature with
Natriumhydrogensulfit (585 mg, 5.62 mmol) versetzt, und anschließend 5 h lang bei 130°C gerührt. Nach dem Abkühlen auf Raumtemperatur wurde das Sodium hydrogen sulfite (585 mg, 5.62 mmol), and then stirred at 130 ° C for 5 h. After cooling to room temperature, the
Reaktionsgemisch mit Wasser versetzt und mit Dichlormethan mehrfach gründlich extrahiert. Die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, abfiltriert, unter vermindertem Druck eingeengt und abschließend säulenchromatographisch gereinigt (Gradient Essigester/Heptan). Auf diese Weise konnte tert-Butyl-4-(4-carbamoyl-1 H-benzimidazol-2-yl)piperidin-1 -carboxylat ( .0 g, 88 % der Theorie) in Form eines farblosen Feststoffes erhalten werden. 1H-NMR (400 MHz, CDC δ, ppm) 9.70 (br. s, 1 H, NH), 8.10 (s, 1 H), 7.60 (s, 1 H), 7.30 (t, 1 H), 5.90 (br. s, 1 H, NH), 3.12 (m, 1 H), 2.10 (m, 2H), 1 .90 (m, 2H), 1 .65 (m, 4H). 1 .50 (s, 9H). Mixed reaction mixture with water and extracted several times with dichloromethane thoroughly. The combined organic phases were then washed over magnesium sulfate dried, filtered off, concentrated under reduced pressure and finally purified by column chromatography (gradient ethyl acetate / heptane). In this way, tert-butyl 4- (4-carbamoyl-1H-benzimidazol-2-yl) piperidine-1-carboxylate (.0 g, 88% of theory) was obtained in the form of a colorless solid. 1 H-NMR (400 MHz, CDC δ, ppm) 9.70 (br.s, 1H, NH), 8.10 (s, 1H), 7.60 (s, 1H), 7.30 (t, 1H), 5.90 (br s, 1H, NH), 3.12 (m, 1H), 2.10 (m, 2H), 1.90 (m, 2H), 1.65 (m, 4H). 1 .50 (s, 9H).
No. A1 -130: 2-(Piperidin-4-yl)-1 H-benzimidazol-4-carboxamid No. A1 -130: 2- (piperidin-4-yl) -1H-benzimidazole-4-carboxamide
tert-Butyl-4-(4-carbamoyl-1 H-benzimidazol-2-yl)piperidin-1 -carboxylat (1 .0 g, 2.9 mmol) wurden bei Raumtemperatur unter Argon in abs. Dichlormethan (10ml_) gelöst und unter intensivem Rühren langsam mit Trifluoressigsäure (2.5 ml_) versetzt. Diese Reaktionslösung ließ man 1 h lang nachrühren mit kontinuierlicher Umsatzkontrolle per DC und anl. HPLC. Im Anschluss daran wurde unter Rühren vorsichtig wäßrige Natriumhydrogencarbonat-Lösung zugegeben bis ein pH-Wert von 9 erreicht war. Die wäßrigen und organischen Phasen wurden gemeinsam vollständig unter vermindertem Druck einrotiert und der zurückbleibende Feststoff mit Ethanol ausgerührt. Die tert -Butyl 4- (4-carbamoyl-1H-benzimidazol-2-yl) piperidine-1-carboxylate (1 .0 g, 2.9 mmol) was added at room temperature under argon in abs. Dissolved dichloromethane (10ml_) and added slowly with vigorous stirring trifluoroacetic acid (2.5 ml_). This reaction solution was allowed to stir for 1 h with continuous conversion control by TLC and anl. HPLC. Subsequently, while stirring, aqueous sodium bicarbonate solution was added carefully until a pH of 9 was reached. The aqueous and organic phases were co-evaporated completely under reduced pressure and the residual solid was stirred with ethanol. The
Ethanolphase wurde über Natriumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Man erhielt auf diese Weise 2-(Piperidin-4-yl)-1 H-benzimidazol-4- carboxamid (300mg, 40% der Theorie) in Form eines farblosen Feststoffs. 1H-NMR (400 MHz, CDaOD δ, ppm) 7.88 (d, 1 H), 7.69 (d, 1 H), 7.29 (t, 1 H), 3.15 (m, 3H), 2.80 (m, 2H), 2.10 (m, 2H), 1 .90 (m, 2H). No. B1 -18: 2-(2,4-Dichlorphenyl)-1 ,3-benzoxazol-4-carboxamid Ethanol phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. There was thus obtained 2- (piperidin-4-yl) -1H-benzimidazole-4-carboxamide (300 mg, 40% of theory) as a colorless solid. 1 H-NMR (400 MHz, CDaOD δ, ppm) 7.88 (d, 1H), 7.69 (d, 1H), 7.29 (t, 1H), 3.15 (m, 3H), 2.80 (m, 2H) , 2.10 (m, 2H), 1 .90 (m, 2H). No. B1 -18: 2- (2,4-dichlorophenyl) -1,3-benzoxazole-4-carboxamide
8 g (40,58 mmol) Methyl-3-hydroxy-2-nitrobenzoat wurden bei Raumtemperatur in 160 ml einer Mischung (1 :1 ) aus Essigsäure und Ethanol gelöst. Die Lösung versetzte man mit 9,971 g (178,55 mmol) Eisenpulver und erhitzte 2 h zum Sieden. Man kühlte auf Raumtemperatur ab, versetzte die Mischung mit 50 ml Wasser und extrahierte das Gemisch zweimal mit 100 ml Essigsäureethylester. Die organische Phase wusch man mit verdünnter Natriumhydrogencarbonat-Lösung neutral und trocknete diese über Natriumsulfat. Das Lösungsmittel entfernte man im Vakuum und man erhält auf diese Weise 6.50 g (95 % der Theorie) des gewünschten Methyl-2-amino-3- hydroxybenzoats. 1H-NMR (400 MHz, DMSO-de δ in ppm) 9.66 (s, 1 H), 7.20 (d, 1 H), 6.81 (d, 1 H), 6.39 (t, 1 H), 6.09 (br. s, 2H), 3.78 (s, 3H). 700 mg (4,19 mmol) Methyl-2- amino-3-hydroxybenzoat, 877 mg (4,19 mmol) 2,4-Dichlorbenzoylchlorid und 210 mg (0.838 mmol) 4-Methylbenzolsulfonsäure Monohydrat wurden in 10 ml Xylol in einem Mikrowellengläschen suspendiert. Man verschloß das Gläschen mit einer 8 g (40.58 mmol) of methyl 3-hydroxy-2-nitrobenzoate were dissolved at room temperature in 160 ml of a mixture (1: 1) of acetic acid and ethanol. The solution was mixed with 9.971 g (178.55 mmol) of iron powder and heated for 2 h to boiling. The mixture was cooled to room temperature, the mixture was mixed with 50 ml of water and the mixture was extracted twice with 100 ml of ethyl acetate. The organic phase was washed neutral with dilute sodium bicarbonate solution and dried over sodium sulfate. The solvent was removed in vacuo to give 6.50 g (95% of theory) of the desired methyl 2-amino-3-hydroxybenzoate. 1 H-NMR (400 MHz, DMSO-de δ in ppm) 9.66 (s, 1H), 7.20 (d, 1H), 6.81 (d, 1H), 6.39 (t, 1H), 6.09 (br s, 2H), 3.78 (s, 3H). 700 mg (4.19 mmol) of methyl 2-amino-3-hydroxybenzoate, 877 mg (4.19 mmol) of 2,4-dichlorobenzoyl chloride and 210 mg (0.838 mmol) of 4-methylbenzenesulfonic acid monohydrate were dissolved in 10 ml of xylene in a microwave vial suspended. One closed the glass with one
Septumkappe und erhitzte das Gemisch in einer Biotage Initiator Sixty Mikrowelle 25 min auf 160 °C. Nach dem Abkühlen auf Raumtemperatur entfernte man das Septum cap and heated the mixture in a Biotage initiator Sixty microwave for 25 min at 160 ° C. After cooling to room temperature, the residue was removed
Lösungsmittel im Vakuum, reinigte das Rohprodukt durch Säulenchromatographie (n- Heptan:Essigsäureethylester 4:1—► Essigsäureethylester) und erhielt 500 mg (35 % d. Th.) Methyl-2-(2,4-dichlorphenyl)-1 ,3-benzoxazol-4-carboxylat. 1H-NMR (CDCb δ in ppm): 8.21 (d, 1 H), 8.08 (d, 1 H), 7.81 (dd, 1 H), 7.59 (d, 1 H), 7.48 (t, 1 H), 7.42 (dd, 1 H), 4.05 (s, 3H). 450 mg (1 ,40 mmol) Methyl-2-(2,4-dichlorphenyl)-1 ,3-benzoxazol-4- carboxylat und 0,838 ml 2 N Natronlauge wurden in 10 ml THF und 2 ml Wasser gelöst. Man rührte die Lösung über Nacht bei Raumtemperatur, wobei ein Feststoff ausfiel. Die Suspension säuerte man mit 2 N Salzsäure an und saugte den Solvent in vacuo, the crude product was purified by column chromatography (n-heptane: ethyl acetate 4: 1 → ethyl acetate) to give 500 mg (35% of theory) of methyl 2- (2,4-dichlorophenyl) -1,3. benzoxazole-4-carboxylate. 1 H-NMR (CDCbδ in ppm): 8.21 (d, 1H), 8.08 (d, 1H), 7.81 (dd, 1H), 7.59 (d, 1H), 7.48 (t, 1H) , 7.42 (dd, 1H), 4.05 (s, 3H). 450 mg (1.40 mmol) of methyl 2- (2,4-dichlorophenyl) -1,3-benzoxazole-4-carboxylate and 0.838 ml of 2N sodium hydroxide solution were dissolved in 10 ml of THF and 2 ml of water. The solution was stirred at room temperature overnight, precipitating a solid. The suspension was acidified with 2 N hydrochloric acid and sucked the
entstandenen Feststoff ab. Diesen trocknete man an der Luft und man erhielt 300 mg (66 % d. Th.) der gewünschten 2-(2,4-Dichlorphenyl)-1 ,3-benzoxazol-4-carbonsäure. 1H-NMR (CDCb δ in ppm): 11 .62 (br. s, 1 H), 8.23-8.18 (m, 2H), 7.88 (d, 1 H), 7.67 (d, 1 H), 7.60 (t, 1 H), 7.49 (dd, 1 H). 250 mg (0,81 mmol) 2-(2,4-Dichlorphenyl)-1 ,3- benzoxazol-4-carbonsäure, 132 mg (0,97 mmol) 1 -Hydroxy-1 H-benzotriazol, 171 mg (0,89 mmol) 1 -(3-Dimethylaminopropyl)-3-ethylcarbodiimid Hydrochlorid und 10 mg DMAP wurden in 5 ml Dichlormethan gelöst. Man rührte 15 min lang bei from the resulting solid. This was dried in air and 300 mg were obtained (66% of theory) of the desired 2- (2,4-dichlorophenyl) -1,3-benzoxazole-4-carboxylic acid. 1 H-NMR (CDCbδ in ppm): 11.62 (br. S, 1H), 8.23-8.18 (m, 2H), 7.88 (d, 1H), 7.67 (d, 1H), 7.60 ( t, 1 H), 7.49 (dd, 1 H). 250 mg (0.81 mmol) of 2- (2,4-dichlorophenyl) -1,3-benzoxazole-4-carboxylic acid, 132 mg (0.97 mmol) of 1-hydroxy-1H-benzotriazole, 171 mg (0, 89 mmol) of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and 10 mg of DMAP were dissolved in 5 ml of dichloromethane. The mixture was stirred for 15 minutes
Raumtemperatur und tropfte dann 1 ,78 ml einer 0,5 M Ammoniak-Lösung in 1 ,4- Dioxan zu. Man rührte 2 h lang bei Raumtemperatur, wusch die organische Phase zweimal mit 0,5 N Salzsäure und einmal mit verdünnter Natriumhydrogencarbonat- Lösung. Das Lösungsmittel entfernte man im Vakuum, suspendierte den Rückstand in Acetonitril und erwärmte diesen im Ultraschallbad. Den Feststoff saugte man ab und trocknet diesen an der Luft. Man erhält so 120 mg (45 % d. Th.) 2-(2,4-Dichlorphenyl)- 1 ,3-benzoxazol-4-carboxamid. 1H-NMR (DMSO-de δ in ppm): 8.42 (br. s, 1 H), 8.33 (d, 1 H), 8.07-8.01 (m, 3H), 7.98 (d, 1 H), 7.71 (d, 1 H), 7.62 (dd, 1 H). Room temperature and then added dropwise to 1, 78 ml of a 0.5 M ammonia solution in 1, 4-dioxane. The mixture was stirred for 2 h at room temperature, the organic phase was washed twice with 0.5 N hydrochloric acid and once with dilute sodium bicarbonate solution. The solvent was removed in vacuo, the residue was suspended in acetonitrile and heated in an ultrasonic bath. The solid was sucked off and dried in air. This gives 120 mg (45% of theory) of 2- (2,4-dichlorophenyl) -1,3-benzoxazole-4-carboxamide. 1 H-NMR (DMSO-de δ in ppm): 8.42 (br.s, 1H), 8.33 (d, 1H), 8.07-8.01 (m, 3H), 7.98 (d, 1H), 7.71 ( d, 1H), 7.62 (dd, 1H).
No. B1 -321 : 2-(Pentafluorethyl)-1 ,3-benzoxazol-4-carboxamid No. B1 -321: 2- (pentafluoroethyl) -1,3-benzoxazole-4-carboxamide
2-Amino-3-hydroxybenzoesäureethylester (250 mg, 1.38 mmol) wurde in abs. THF (Tetrahydrofuran) (3 ml) gelöst und unter Argon auf eine Temperatur von -78 °C eingekühlt. Danach wurde langsam tropfenweise eine Lösung von Ethyl 2-amino-3-hydroxybenzoate (250 mg, 1.38 mmol) was dissolved in abs. Dissolved THF (tetrahydrofuran) (3 ml) and cooled to a temperature of -78 ° C under argon. Thereafter, slowly a dropwise solution of
Pentafluorpropionsäureanhydrid (471 mg, 1 .52 mmol) in abs. THF (2 ml) zugegeben und das Reaktionsgemisch 30 min lang bei -78 °C und danach 1 h lang bei Pentafluoropropionic anhydride (471 mg, 1.52 mmol) in abs. THF (2 ml) was added and the reaction mixture was kept at -78 ° C for 30 minutes and then for 1 hour
Raumtemperatur nachgerührt. Nach der Zugabe von Wasser wurde die wässrige Phase mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden danach nochmals mit Wasser extrahiert, über Magnesiumsulfat getrocknet, abfiltriert und eingeengt. Durch säulenchromatographische Reinigung des Room temperature stirred. After the addition of water, the aqueous phase was extracted several times with dichloromethane. The combined organic phases were then extracted again with water, dried over magnesium sulfate, filtered off and concentrated. By column chromatography of the
resultierenden Rohproduktes konnte Ethyl-2-(pentafluorethyl)-1 ,3-benzoxazol-4- carboxylat (400 mg, 94 % der Theorie) isoliert werden. Ethyl-2-(pentafluorethyl)- ,3- benzoxazol-4-carboxylat (200 mg, 0.65 mmol) wurde danach in abs. THF gelöst (1 ml). Nach der Zugabe von Wasser (5 ml) und Natriumhydroxid (65 mg, 1 .62 mmol) wurde das erhaltene Reaktionsgemisch 3 h lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurde verdünnte Salzsäure vorsichtig zugegeben, so daß ein pH-Wert im leicht sauren Bereich erreicht wurde. Die wäßrige Phase wurde intensiv mehrfach mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden danach nochmals mit Wasser extrahiert, über Magnesiumsulfat getrocknet, abfiltriert und eingeengt. Auf diese Weise konnte 2-(Pentafluorethyl)-1 ,3-benzoxazol-4- carbonsäure (190 mg, 99 % der Theorie) erhalten werden, von der dann eine resulted in ethyl 2- (pentafluoroethyl) -1,3-benzoxazole-4 carboxylate (400 mg, 94% of theory). Ethyl 2- (pentafluoroethyl) -3-benzoxazole-4-carboxylate (200 mg, 0.65 mmol) was then dissolved in abs. THF dissolved (1 ml). After the addition of water (5 ml) and sodium hydroxide (65 mg, 1.62 mmol), the resulting reaction mixture was stirred for 3 hours under reflux conditions. After cooling to room temperature, dilute hydrochloric acid was added cautiously to reach a slightly acidic pH. The aqueous phase was extracted intensively several times with ethyl acetate. The combined organic phases were then extracted again with water, dried over magnesium sulfate, filtered off and concentrated. In this way, 2- (pentafluoroethyl) -1, 3-benzoxazole-4-carboxylic acid (190 mg, 99% of theory) were obtained, then from a
Teilmenge (130 mg, 0.46 mmol) in Dichlormethan (2 ml) gelöst und mit Partly dissolved (130 mg, 0.46 mmol) in dichloromethane (2 ml) and washed with
Oxalsäuredichlorid (0.03 ml, 0.39 mmol) sowie einer katalytischen Menge N,N- Dimethylformamid versetzt wurde. Das Reaktionsgemisch wurde 15 min lang bei Raumtemperatur und danach 3 h lang bei 70 °C gerührt und im Anschluß daran komplett eingeengt. Nach Zugabe von Toluol wurde erneut eingeengt und das so erhaltene Säurechlorid ohne weitere Aufreinigung in Tetra hydrofu ran (5 ml) gelöst. Dann wurde unter Kühlung Ammoniak (g) eingeleitet und 1 h lang bei Raumtemperatur nachgerührt. Das Reaktionsgemisch wurde vollständig eingeengt und der Rückstand säulenchromatographisch (Kieselgel, Gradient mit n-Heptan und Essigester) gereinigt. Man erhielt 2-(Pentafluorethyl)-1 ,3-benzoxazol-4-carboxamid in Form eines farblosen Feststoffs (21 mg, 16 % der Theorie). 1H-NMR (400 MHz, CDC δ, ppm) 8.37 (d, 1 H), 8.36 (br. s, 1 H, NH), 7.88 (d, 1 H), 7.71 (dd, 1 H), 5.93 (br. s, 1 H, NH). Oxalic acid dichloride (0.03 ml, 0.39 mmol) and a catalytic amount of N, N-dimethylformamide was added. The reaction mixture was stirred for 15 minutes at room temperature and then for 3 hours at 70 ° C and then completely concentrated. After addition of toluene was concentrated again and the resulting acid chloride without further purification in tetrahydrofuran (5 ml). Then ammonia (g) was introduced with cooling and stirred for 1 h at room temperature. The reaction mixture was completely concentrated and the residue was purified by column chromatography (silica gel, gradient with n-heptane and ethyl acetate). There was obtained 2- (pentafluoroethyl) -1,3-benzoxazole-4-carboxamide as a colorless solid (21 mg, 16% of theory). 1 H-NMR (400 MHz, CDC δ, ppm) 8.37 (d, 1H), 8.36 (br.s, 1H, NH), 7.88 (d, 1H), 7.71 (dd, 1H), 5.93 (br s, 1H, NH).
No. C1 -321 : 2-(Pentafluorethyl)-1 ,3-benzothiazol-4-carboxamid No. C1 -321: 2- (pentafluoroethyl) -1,3-benzothiazole-4-carboxamide
3-Chlor-2-nitrobenzoesäure (500 mg, 2.48 mmol) und Natriumsulfid-nonahydrat (1.61 g, 6.69 mmol) wurden in Wasser gelöst und mehrere Stunden lang unter Rückflußbedingungen gerührt. Nach dem Abkühlen auf Raumtemperatur wurde das Reaktionsgemisch mit verdünnter Salzsäure auf pH 5 eingestellt. Der dabei erhaltene Niederschlag wurde abgesaugt, mehrmals mit Wasser nachgewaschen, gründlich getrocknet und lieferte auf diese Weise 2-Amino-3-Hydrothiobenzoesäure in Form eines farblosen Feststoffs (250 mg, 59% der Theorie). 2-Amino-3- hydrothiobenzoesäure (250 mg, 1 .48 mmol) wurde in abs. THF (Tetra hydrofu ran) (5 ml) gelöst und unter Argon auf eine Temperatur von -78 °C eingekühlt. Danach wurde langsam tropfenweise eine Lösung von Pentafluorpropionsäureanhydrid (560 mg, 1 .77 mmol) in abs. THF (3 ml) zugegeben und das Reaktionsgemisch 30 min lang bei -78 °C und danach 1 h lang bei Raumtemperatur nachgerührt. Das Lösemittel wurde einrotiert und der Rückstand mit Dichlormethan aufgenommen. Nach der Zugabe von Wasser wurde die wässrige Phase mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden danach nochmals mit Wasser extrahiert, über Magnesiumsulfat getrocknet, abfiltriert und eingeengt. Durch 3-Chloro-2-nitrobenzoic acid (500 mg, 2.48 mmol) and sodium sulfide nonahydrate (1.61 g, 6.69 mmol) were dissolved in water and allowed to stand for several hours Reflux conditions stirred. After cooling to room temperature, the reaction mixture was adjusted to pH 5 with dilute hydrochloric acid. The resulting precipitate was filtered off with suction, washed several times with water, dried thoroughly and provided in this way 2-amino-3-hydrothiobenzoic acid in the form of a colorless solid (250 mg, 59% of theory). 2-amino-3-hydrothiobenzoic acid (250 mg, 1.48 mmol) was dissolved in abs. Dissolved THF (tetrahydrofuran) (5 ml) and cooled under argon to a temperature of -78 ° C. Thereafter, slowly a dropwise solution of pentafluoropropionic anhydride (560 mg, 1 .77 mmol) in abs. THF (3 ml) was added and the reaction mixture was stirred for 30 minutes at -78 ° C and then for 1 h at room temperature. The solvent was evaporated and the residue taken up in dichloromethane. After the addition of water, the aqueous phase was extracted several times with dichloromethane. The combined organic phases were then extracted again with water, dried over magnesium sulfate, filtered off and concentrated. By
säulenchromatographische Reinigung des resultierenden Rohproduktes konnte 2-column chromatographic purification of the resulting crude product was 2-
(Pentafluorethyl)-1 ,3-benzothiazol-4-carbonsäure (230 mg, 52 % der Theorie) erhalten werden, das dann in Dichlormethan (4 ml) gelöst und mit Oxalsäuredichlorid (0.06 ml, 0.78 mmol) sowie einer katalytischen Menge Ν,Ν-Dimethylformamid versetzt wurde. Das Reaktionsgemisch wurde 15 min lang bei Raumtemperatur und danach 3 h lang bei 70 °C gerührt und im Anschluß daran komplett eingeengt. Nach Zugabe von Toluol wurde erneut eingeengt und das so erhaltene Säurechlorid ohne weitere Aufreinigung in Tetra hydrofu ran (5 ml) gelöst. Dann wurde unter Kühlung Ammoniak (g) eingeleitet und 1 h lang bei Raumtemperatur nachgerührt. Das Reaktionsgemisch wurde vollständig eingeengt und der Rückstand säulenchromatographisch (Kieselgel, (Pentafluoroethyl) -1,3-benzothiazole-4-carboxylic acid (230mg, 52% of theory), which was then dissolved in dichloromethane (4ml) and treated with oxalic acid dichloride (0.06ml, 0.78mmol) and a catalytic amount Ν, Ν-dimethylformamide was added. The reaction mixture was stirred for 15 minutes at room temperature and then for 3 hours at 70 ° C and then completely concentrated. After addition of toluene was concentrated again and the resulting acid chloride without further purification in tetrahydrofuran (5 ml). Then ammonia (g) was introduced with cooling and stirred for 1 h at room temperature. The reaction mixture was completely concentrated and the residue was purified by column chromatography (silica gel,
Gradient mit n-Heptan und Essigester) gereinigt. Man erhielt 2-(Pentafluorethyl)-1 ,3- benzothiazol-4-carboxamid in Form eines farblosen Feststoffs (60 mg, 28 % der Theorie). 1H-NMR (400 MHz, CDCb δ, ppm) 9.11 (br. s, 1 H, NH), 8.59 (d, 1 H), 8.19 (d, 1 H), 7.73 (dd, 1 H), 6.03 (br. s, 1 H, NH); 19F-NMR (375 MHz, de-DMSO δ, ppm) -82.7, - 108.9. Gradient with n-heptane and ethyl acetate). 2- (Pentafluoroethyl) -1,3-benzothiazole-4-carboxamide was obtained in the form of a colorless solid (60 mg, 28% of theory). 1 H-NMR (400 MHz, CDCb δ, ppm) 9.11 (br. S, 1H, NH), 8.59 (d, 1H), 8.19 (d, 1H), 7.73 (dd, 1H), 6.03 (br, s, 1H, NH); 19 F-NMR (375 MHz, de-DMSO δ, ppm) -82.7, - 108.9.
In Analogie zu den oben angeführten und in den nachstehenden Tabellen rezitierten Herstellungsbeispielen und unter Berücksichtigung der allgemeinen Angaben zur Herstellung von substituierten 2-Amidobenzimidazolen, 2-Amidobenzoxazolen und 2- Amidobenzothiazolen der allgemeinen Formel (I) erhält man die nachfolgend genannten Verbindungen. By analogy with the preparation examples recited above and recited in the tables below, and taking into account the general information on the preparation of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2- Amidobenzothiazolen of the general formula (I) gives the compounds mentioned below.
A1 . Verbindungen A1 -1 bis A1 -1000 der allgemeinen Formel (I), worin R\ R2 und R3 für Wasserstoff stehen und Q, W, Z\ Z2 sowie R4 den Definitionen (Nos 1 bis 1000; entsprechend Verbindungen A1 -1 bis A1 -1000) in der folgenden Tabelle 1 entsprechen A1. Compounds A1 -1 to A1 -1000 of the general formula (I) in which R 1, R 2 and R 3 are hydrogen and Q, W, Z 1, Z 2 and R 4 are each as defined above (Nos 1 to 1000; 1 to A1-1000) in the following Table 1
Tabelle 1 Table 1
A2. Verbindungen A2-1 bis A2-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Trifluormethyl steht, X für N-R4 steht und Q, W, Z1 , Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A2-1 bis A2-1000) entsprechen. A2. Compounds A2-1 to A2-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is trifluoromethyl, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A2-1 to A2-1000).
A3. Verbindungen A3-1 bis A3-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Methyl steht, X für N-R4 steht und Q, W, Z Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A3-1 bis A3-1000) entsprechen. A3. Compounds A3-1 to A3-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is methyl, X is NR 4 and Q, W, ZZ 2 and R 4 is the respective individual compound the residue definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A3-1 to A3-1000).
A4. Verbindungen A4-1 bis A4-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Fluor steht, X für N-R4 steht und Q, W, Z1 , Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A4-1 bis A4-1000) entsprechen. A4. Compounds A4-1 to A4-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is fluorine, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A4-1 to A4-1000).
A5. Verbindungen A5-1 bis A5-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Chlor steht, X für N-R4 steht und Q, W, Z1 , Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A5-1 bis A5-1000) entsprechen. A6. Verbindungen A6-1 bis A6-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Brom steht, X für N-R4 steht und Q, W, Z1 , Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A6-1 bis A6-1000) entsprechen. A5. Compounds A5-1 to A5-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is chlorine, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A5-1 to A5-1000). A6. Compounds A6-1 to A6-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is bromine, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A6-1 to A6-1000).
A7. Verbindungen A7-1 bis A7-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für lod steht, X für N-R4 steht und Q, W, Z\ Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A7-1 bis A7-1000) entsprechen. A7. Compounds A7-1 to A7-1000 of the general formula (I) wherein R 1 and R 3 are hydrogen, R 2 is iodine, X is NR 4 and Q, W, Z \ Z 2 and R 4 for the corresponding individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A7-1 to A7-1000).
A8. Verbindungen A8-1 bis A8-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Ethyl steht, X für N-R4 steht und Q, W, Z1 , Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A8-1 bis A8-1000) entsprechen. A8. Compounds A8-1 to A8-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is ethyl, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A8-1 to A8-1000).
A9. Verbindungen A9-1 bis A9-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Cyclopropyl steht, X für N-R4 steht und Q, W, Z1 , Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A9-1 bis A9-1000) entsprechen. A9. Compounds A9-1 to A9-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is cyclopropyl, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A9-1 to A9-1000).
A10. Verbindungen A10-1 bis A10-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Trimethylsilylethinyl steht, X für N-R4 steht und Q, W, Z Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten A10. Compounds A10-1 to A10-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is trimethylsilylethynyl, X is NR 4 and Q, W, ZZ 2 and R 4 is the respective individual compound those mentioned in Table 1
Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A10-1 bis A10-1000) entsprechen. Residue definitions (Nos 1 to 1000, corresponding to compounds A10-1 to A10-1000).
A1 1 . Verbindungen A1 1 -1 bis A1 1 -1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Ethinyl steht, X für N-R4 steht und Q, W, Z1 , Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A1 1 -1 bis A1 1 -1000) entsprechen. A1 1. Compounds A1 1 -1 to A1 1 -1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is ethynyl, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 for the respective individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A1 1 -1 to A1 1 -1000).
A12. Verbindungen A12-1 bis A12-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Phenyl steht, X für N-R4 steht und Q, W, Z\ Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A12-1 bis A12-1000) entsprechen. A12. Compounds A12-1 to A12-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is phenyl, X is NR 4 and Q, W, Z \ Z 2 and R 4 for the particular individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A12-1 to A12-1000).
A13. Verbindungen A13-1 bis A13-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für iso-Propyl steht, X für N-R4 steht und Q, W, Z\ Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A13-1 bis A13-1000) entsprechen. A13. Compounds A13-1 to A13-1000 of general formula (I) wherein R 1 and R 3 are hydrogen, R 2 is iso-propyl, X is NR 4 and Q, W, Z \ Z 2 and R 4 for the particular individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A13-1 to A13-1000).
A14. Verbindungen A14-1 bis A14-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Difiuormethyl steht, X für N-R4 steht und Q, W, Z1, Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten A14. Compounds A14-1 to A14-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is difluoromethyl, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compound mentioned in Table 1
Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A14-1 bis A14-1000) entsprechen. A15. Verbindungen A15-1 bis A15-1000 der allgemeinen Formel (I), worin R1 und R2 für Wasserstoff stehen, R3 für Fluor steht, X für N-R4 steht und Q, W, Z\ Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A15-1 bis A15-1000) entsprechen. A16. Verbindungen A16-1 bis A16-1000 der allgemeinen Formel (I), worin R1 und R2 für Wasserstoff stehen, R3 für Chlor steht, X für N-R4 steht und Q, W, Z\ Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A16-1 bis A16-1000) entsprechen. A17. Verbindungen A17-1 bis A17-1000 der allgemeinen Formel (I), worin R1 und R2 für Wasserstoff stehen, R3 für Brom steht, X für N-R4 steht und Q, W, Z\ Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A17-1 bis A17-1000) entsprechen. A18. Verbindungen A18-1 bis A18-1000 der allgemeinen Formel (I), worin R1 und R2 für Wasserstoff stehen, R3 für Trifluormethyl steht, X für N-R4 steht und Q, W, Z\ Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Residue definitions (Nos 1 to 1000, corresponding to compounds A14-1 to A14-1000). A15. Compounds A15-1 to A15-1000 of the general formula (I) wherein R 1 and R 2 are hydrogen, R 3 is fluorine, X is NR 4 and Q, W, Z \ Z 2 and R 4 for the Respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A15-1 to A15-1000). A16. Compounds A16-1 to A16-1000 of the general formula (I) wherein R 1 and R 2 are hydrogen, R 3 is chlorine, X is NR 4 and Q, W, Z \ Z 2 and R 4 for the Respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A16-1 to A16-1000). A17. Compounds A17-1 to A17-1000 of the general formula (I) wherein R 1 and R 2 are hydrogen, R 3 is bromine, X is NR 4 and Q, W, Z \ Z 2 and R 4 for the corresponding individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A17-1 to A17-1000). A18. Compounds A18-1 to A18-1000 of the general formula (I) wherein R 1 and R 2 are hydrogen, R 3 is trifluoromethyl, X is NR 4 and Q, W, Z \ Z 2 and R 4 for the respective individual compound mentioned in Table 1
Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A18-1 bis A18-1000) entsprechen. A19. Verbindungen A19-1 bis A19-1000 der allgemeinen Formel (I), worin R1 und R2 für Wasserstoff stehen, R3 für Methyl steht, X für N-R4 steht und Q, W, Z1, Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A19-1 bis A19-1000) entsprechen. Residue definitions (Nos 1 to 1000, corresponding to compounds A18-1 to A18-1000). A19. Compounds A19-1 to A19-1000 of the general formula (I) in which R 1 and R 2 are hydrogen, R 3 is methyl, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A19-1 to A19-1000).
A20. Verbindungen A20-1 bis A20-1000 der allgemeinen Formel (I), worin R2 und R3 für Wasserstoff stehen, R1 für Fluor steht, X für N-R4 steht und Q, W, Z1, Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A20-1 bis A20-1000) entsprechen. A20. Compounds A20-1 to A20-1000 of the general formula (I) in which R 2 and R 3 are hydrogen, R 1 is fluorine, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A20-1 to A20-1000).
A21 . Verbindungen A21 -1 bis A21 -1000 der allgemeinen Formel (I), worin R2 und R3 für Wasserstoff stehen, R1 für Chlor steht, X für N-R4 steht und Q, W, Z1, Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A21-1 bis A21-1000) entsprechen. A21. Compounds A21-1 to A21-1000 of the general formula (I) in which R 2 and R 3 are hydrogen, R 1 is chlorine, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A21-1 to A21-1000).
A22. Verbindungen A22-1 bis A22-1000 der allgemeinen Formel (I), worin R2 und R3 für Wasserstoff stehen, R1 für Brom steht, X für N-R4 steht und Q, W, Z1, Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A22-1 bis A22-1000) entsprechen. A22. Compounds A22-1 to A22-1000 of the general formula (I) in which R 2 and R 3 are hydrogen, R 1 is bromine, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A22-1 to A22-1000).
A23. Verbindungen A23-1 bis A23-1000 der allgemeinen Formel (I), worin R2 und R3 für Wasserstoff stehen, R1 für Trifluormethyl steht, X für N-R4 steht und Q, W, Z1, Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten A23. Compounds A23-1 to A23-1000 of the general formula (I) in which R 2 and R 3 are hydrogen, R 1 is trifluoromethyl, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compound mentioned in Table 1
Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A23-1 bis A23-1000) entsprechen. Residue definitions (Nos 1 to 1000, corresponding to compounds A23-1 to A23-1000).
A24. Verbindungen A24-1 bis A24-1000 der allgemeinen Formel (I), worin R2 und R3 für Wasserstoff stehen, R1 für Methyl steht, und Q, W, Z1, Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; A24. Compounds A24-1 to A24-1000 of the general formula (I) in which R 2 and R 3 are hydrogen, R 1 is methyl, and Q, W, Z 1 , Z 2 and R 4 for the respective individual compound denote in Table 1 mentioned residue definitions (Nos 1 to 1000;
entsprechend Verbindungen A24-1 bis A24-1000) entsprechen. corresponding to compounds A24-1 to A24-1000).
A25. Verbindungen A25-1 bis A25-1000 der allgemeinen Formel (I), worin R1 und R2 für Fluor stehen, R3 für Wasserstoff steht, X für N-R4 steht und Q, W, Z1, Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A25-1 bis A25-1000) entsprechen. A25. Compounds A25-1 to A25-1000 of the general formula (I) in which R 1 and R 2 are fluorine, R 3 is hydrogen, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 for the particular individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A25-1 to A25-1000).
A26. Verbindungen A26-1 bis A26-1000 der allgemeinen Formel (I), worin R1 und R2 für Methyl stehen, R3 für Wasserstoff steht, X für N-R4 steht und Q, W, Z\ Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A26-1 bis A26-1000) entsprechen. A26. Compounds A26-1 to A26-1000 of the general formula (I) wherein R 1 and R 2 are methyl, R 3 is hydrogen, X is NR 4 and Q, W, Z \ Z 2 and R 4 for the corresponding individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A26-1 to A26-1000).
A27. Verbindungen A27-1 bis A27-1000 der allgemeinen Formel (I), worin R1 und R2 mit den Atomen, an die sie gebunden sind, einen annelierten Phenylring bilden, R3 für Wasserstoff steht, X für N-R4 steht und Q, W, Z1 , Z2 sowie R4 für die jeweilige A27. Compounds A27-1 to A27-1000 of the general formula (I) in which R 1 and R 2 together with the atoms to which they are attached form a fused phenyl ring, R 3 is hydrogen, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 for the respective
Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; Single compound the radical definitions given in Table 1 (Nos 1 to 1000;
entsprechend Verbindungen A27-1 bis A27-1000) entsprechen. A28. Verbindungen A28-1 bis A28-1000 der allgemeinen Formel (I), worin R2 und R3 mit den Atomen, an die sie gebunden sind, einen annelierten Phenylring bilden, R1 für Wasserstoff steht, und Q, W, Z1 , Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A28-1 bis A28-1000) entsprechen. corresponding to compounds A27-1 to A27-1000). A28. Compounds A28-1 to A28-1000 of the general formula (I) in which R 2 and R 3 together with the atoms to which they are attached form a fused phenyl ring, R 1 is hydrogen, and Q, W, Z 1 , Z 2 and R 4 for the respective individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A28-1 to A28-1000).
A29. Verbindungen A29-1 bis A29-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Methoxy steht, X für N-R4 steht und Q, W, Z\ Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A29-1 bis A29-1000) entsprechen. A29. Compounds A29-1 to A29-1000 of the general formula (I) wherein R 1 and R 3 are hydrogen, R 2 is methoxy, X is NR 4 and Q, W, Z \ Z 2 and R 4 for the corresponding individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A29-1 to A29-1000).
A30. Verbindungen A30-1 bis A30-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Trifluormethoxy steht, X für N-R4 steht und Q, W, Z Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten A30. Compounds A30-1 to A30-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is trifluoromethoxy, X is NR 4 and Q, W, ZZ 2 and R 4 for the respective individual compound those mentioned in Table 1
Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A30-1 bis A30-1000) entsprechen. Residue definitions (nos 1 to 1000, corresponding to compounds A30-1 to A30-1000).
A31 . Verbindungen A31 -1 bis A31 -1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Trifluormethylthio steht, X für N-R4 steht und Q, W, Z1 , Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Resiedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A31 -1 bis A31 -1000) entsprechen. A31. Compounds A31-1 to A31-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is trifluoromethylthio, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compound mentioned in Table 1 Resiedefinitionen (Nos 1 to 1000, corresponding to compounds A31 -1 to A31 -1000) correspond.
A32. Verbindungen A32-1 bis A32-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Difluormethoxy steht, X für N-R4 steht und Q, W, Z\ Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten A32. Compounds A32-1 to A32-1000 of the general formula (I) wherein R 1 and R 3 are hydrogen, R 2 is difluoromethoxy, X is NR 4 and Q, W, Z \ Z 2 and R 4 for the respective individual compound mentioned in Table 1
Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A32-1 bis A32-1000) entsprechen. A33. Verbindungen A33-1 bis A33-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Ethenyl steht, X für N-R4 steht und Q, W, Z\ Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A33-1 bis A33-1000) entsprechen. A34. Verbindungen A34-1 bis A 34-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Cyclobutyl steht, X für N-R4 steht und Q, W, Z1, Z2 sowieResidue definitions (Nos 1 to 1000, corresponding to compounds A32-1 to A32-1000). A33. Compounds A33-1 to A33-1000 of the general formula (I) wherein R 1 and R 3 are hydrogen, R 2 is ethenyl, X is NR 4 and Q, W, Z \ Z 2 and R 4 for the corresponding individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A33-1 to A33-1000). A34. Compounds A34-1 to A 34-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is cyclobutyl, X is NR 4 and Q, W, Z 1 , Z 2 and
R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A34-1 bis A34-1000) entsprechen. A35. Verbindungen A35-1 bis A35-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Cyclopentyl steht, X für N-R4 steht und Q, W, Z1, Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten R 4 for the respective individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A34-1 to A34-1000). A35. Compounds A35-1 to A35-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is cyclopentyl, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compound mentioned in Table 1
Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A35-1 bis A35-1000) entsprechen. Residue definitions (Nos 1 to 1000, corresponding to compounds A35-1 to A35-1000).
A36. Verbindungen A36-1 bis A36-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für 4-Chlorphenyl steht, X für N-R4 steht und Q, W, Z\ Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten A36. Compounds A36-1 to A36-1000 of the general formula (I) wherein R 1 and R 3 are hydrogen, R 2 is 4-chlorophenyl, X is NR 4 and Q, W, Z \ Z 2 and R 4 for the particular individual compound mentioned in Table 1
Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A36-1 bis A36-1000) entsprechen. Residue definitions (nos 1 to 1000, corresponding to compounds A36-1 to A36-1000).
A37. Verbindungen A37-1 bis A37-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für 2-Thiophenyl steht, X für N-R4 steht und Q, W, Z\ Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Resiedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A37-1 bis A37-1000) entsprechen. A37. Compounds A37-1 to A37-1000 of the general formula (I) wherein R 1 and R 3 are hydrogen, R 2 is 2-thiophenyl, X is NR 4 and Q, W, Z \ Z 2 and R 4 for the particular individual compound mentioned in Table 1 Resident definitions (Nos 1 to 1000, corresponding to compounds A37-1 to A37-1000) correspond.
A38. Verbindungen A38-1 bis A38-1000 der aligemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für 2-Furanyl steht, X für N-R4 steht und Q, W, Z\ Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A38-1 bis A38-1000) entsprechen. A38. Compounds A38-1 to A38-1000 of the general formula (I) wherein R 1 and R 3 are hydrogen, R 2 is 2-furanyl, X is NR 4 and Q, W, Z \ Z 2 and R 4 for the particular individual compound, the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A38-1 to A38-1000).
A39. Verbindungen A39-1 bis A39-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Cyclohexyl steht, X für N-R4 steht und Q, W, Z1, Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten A39. Compounds A39-1 to A39-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is cyclohexyl, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compound mentioned in Table 1
Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A39-1 bis A39-1000) entsprechen. A40. Verbindungen A40-1 bis A40-1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für 2-Tetrahydrofuranyl steht, X für N-R4 steht und Q, W, Z1, Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten Residue definitions (Nos 1 to 1000, corresponding to compounds A39-1 to A39-1000). A40. Compounds A40-1 to A40-1000 of the general formula (I) wherein R 1 and R 3 are hydrogen, R 2 is 2-tetrahydrofuranyl, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 for each individual compound mentioned in Table 1
Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A40-1 bis A40-1000) entsprechen. Residue definitions (Nos 1 to 1000, corresponding to compounds A40-1 to A40-1000).
A41 . Verbindungen A41 -1 bis A41 -1000 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Methoxyethoxy steht, X für N-R4 steht und Q, W, Z1, Z2 sowie R4 für die jeweilige Einzelverbindung den in Tabelle 1 genannten A41. Compounds A41-1 to A41-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is methoxyethoxy, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compound mentioned in Table 1
Restedefinitionen (Nos 1 bis 1000; entsprechend Verbindungen A41 -1 bis A41-1000) entsprechen. Residue definitions (Nos 1 to 1000, corresponding to compounds A41-1 to A41-1000).
B1 . Verbindungen B1 -1 bis B1 -700 der allgemeinen Formel (I), worin R\ R2 und R3 für Wasserstoff stehen und Q, W, Z1sowie Z2 den Definitionen (Nos 1 bis 700; B1. Compounds B1 -1 to B1 -700 of the general formula (I) in which R \ R 2 and R 3 are hydrogen and Q, W, Z 1 and Z 2 are the definitions (Nos 1 to 700;
entsprechend Verbindungen B1 -1 bis B1 -700) in der folgenden Tabelle 2 entsprechen corresponding to compounds B1 -1 to B1 -700) in the following Table 2
Tabelle 2 Table 2
No. Q w z1 Z2 No. Q wz 1 Z 2
1 — i, /) 0 H H 1 - i, / ) 0 HH
2 \\ //~Η 0 H H 2 \\ // ~ Η 0 HH
3 (\ ^0H 0 H H 3 (\ ^ 0H 0 HH
4 0 H H 4 0 H H
5 0 H H 5 0 H H
6 ■ r\ 0 H H 6 ■ r \ 0 H H
7 0 H H 7 0 H H
CF3 CF 3
8 0 H H 8 0 H H
F  F
9 / ~ \ 9 / ~ \
/ ^ }}— F 0 H H  / ^}} - F 0 H H
Cl Cl
10 0 H H 10 0 H H
\ /^Cl \ / ^ Cl
F  F
11 — \\ / --ci 0 H H  11 - \\ / --ci 0 H H
\\ /  \\ /
F  F
12 0 H H 12 0 HH
No. Q w z1 Z2 No. Q wz 1 Z 2
70 0 H H 70 0 H H
71 0 H H / 71 0 H H /
72 /=λ N— ^ 0 H H 72 / = λ N- ^ 0 HH
73 =\ /— N 0 H H 73 = \ / - N 0 H H
74 - £X < 0 H H 74 - £ X <0 H H
75 0 H H 75 0 H H
76 0 H H 76 0 H H
; / ; /
77 0 H H  77 0 H H
78 /— ( 0 H H 78 / - (0 H H
79 -<] 0 H H 79 - <] 0 H H
80 0 H H 80 0 H H
81 0 H H 81 0 H H
82 0 H H 82 0 H H
83 KD 0 H H 83 KD 0 H H
84 0 H H 84 0 H H
85 N ' 0 H H 85 N ' 0 HH
H o. Q W z1 Z2 H o. QW z 1 Z 2
131 ,NH 0 H H 131, NH 0 H H
132 0 H H 132 0 H H
133 0 H H 133 0 H H
\.,, NH \ . , NH
134 0 H H 134 0 H H
135 / \ NH 0 H H 135 / \ NH 0 H H
136 _,. H 0 H H 136 _. H 0 HH
137 : < ,N— 0 H H 137: <, N- 0 H H
138 0 H H 138 0 H H
139 H 0 H H 139 H 0 H H
\  \
140 ( N— 0 H H 140 (N-0 H H
141 0 H H 141 0 H H
142 0 H H 142 0 H H
143 0 H H 143 0 H H
144 0 H H 144 0 H H
145 0 H H 145 0 HH
No. Q w z1 Z2 " Ii" No. Q wz 1 Z 2 " Ii "
361 0 ΎΥ 361 0 ΎΥ
"ΊΪ" " ΊΪ "
362 0  362 0
ΊΪ" ΊΪ "
363 0  363 0
F F
364 0 H H  364 0 H H
365 0 H H 365 0 H H
366 0 H H 366 0 H H
381 0 H 381 0 H
0  0
/  /
382 0 H 382 0 H
0  0
/  /
383 s H H 383 s H H
384 0 H 384 0 H
''
385 0 H H 385 0 H H
386 0 H H 386 0 HH
B2. Verbindungen B2-1 bis B2-700 der aligemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Fluor steht, X für O steht und Q, W, Z1, Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; B2. Compounds B2-1 to B2-700 of the general formula (I) wherein R 1 and R 3 are hydrogen, R 2 is fluorine, X is O and Q, W, Z 1 , Z 2 for the respective Single compound the radical definitions given in Table 2 (Nos 1 to 700;
entsprechend Verbindungen B2-1 bis B2-700) entsprechen. corresponding to compounds B2-1 to B2-700).
B3. Verbindungen B3-1 bis B3-700 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Chlor steht, X für O steht und Q, W, Z1 , Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; B3. Compounds B3-1 to B3-700 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is chlorine, X is O and Q, W, Z 1 , Z 2 for each individual compound in Table 2 remainder definitions (Nos 1 to 700;
entsprechend Verbindungen B3-1 bis B3-700) entsprechen. corresponding to compounds B3-1 to B3-700).
B4. Verbindungen B4-1 bis B4-700 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Brom steht, X für O steht und Q, W, Z1 , Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; B4. Compounds B4-1 to B4-700 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is bromine, X is O and Q, W, Z 1 , Z 2 for each individual compound in Table 2 remainder definitions (Nos 1 to 700;
entsprechend Verbindungen B4-1 bis B4-700) entsprechen. corresponding to compounds B4-1 to B4-700).
B5. Verbindungen B5-1 bis B5-700 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für lod steht, X für O steht und Q, W, Z\ Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; B5. Compounds B5-1 to B5-700 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is iodine, X is O and Q, W, Z \ Z 2 for the particular individual compound denoted in Table 2 referred to residue definitions (Nos 1 to 700;
entsprechend Verbindungen B5-1 bis B5-700) entsprechen. corresponding to compounds B5-1 to B5-700).
B6. Verbindungen B6-1 bis B6-700 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Trifluormethyl steht, X für O steht und Q, W, Z1 , Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; entsprechend Verbindungen B6-1 bis B6-700) entsprechen. B6. Compounds B6-1 to B6-700 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is trifluoromethyl, X is O and Q, W, Z 1 , Z 2 for each individual compound in Table 2, the remaining definitions (Nos 1 to 700, corresponding to compounds B6-1 to B6-700).
B7. Verbindungen B7-1 bis B7-700 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Methyl steht, X für O steht und Q, W, Z Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; B7. Compounds B7-1 to B7-700 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is methyl, X is O and Q, W, ZZ 2 for each individual compound are those shown in Table 2 mentioned residue definitions (Nos 1 to 700;
entsprechend Verbindungen B7-1 bis B7-700) entsprechen. corresponding to compounds B7-1 to B7-700).
B8. Verbindungen B8-1 bis B8-700 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Methoxy steht, X für O steht und Q, W, Z1 , Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; entsprechend Verbindungen B8-1 bis B8-700) entsprechen. B9. Verbindungen B9-1 bis B9-700 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Trifluormethoxy steht, X für O steht und Q, W, Z1, Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; entsprechend Verbindungen B9-1 bis B9-700) entsprechen. B8. Compounds B8-1 to B8-700 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is methoxy, X is O and Q, W, Z 1 , Z 2 for each individual compound in Table 2, the remaining definitions (Nos 1 to 700, corresponding to compounds B8-1 to B8-700). B9. Compounds B9-1 to B9-700 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is trifluoromethoxy, X is O and Q, W, Z 1 , Z 2 for each individual compound in Table 2, remaining definitions (Nos 1 to 700, corresponding to compounds B9-1 to B9-700).
B10. Verbindungen B10-1 bis B10-700 der allgemeinen Formel (I), worin R1 und R2 für Wasserstoff stehen, R3 für Fluor steht, X für O steht und Q, W, Z\ Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; B10. Compounds B10-1 to B10-700 of the general formula (I) in which R 1 and R 2 are hydrogen, R 3 is fluorine, X is O and Q, W, Z \ Z 2 for the particular individual compound denoted in Table 2 referred to residue definitions (Nos 1 to 700;
entsprechend Verbindungen B10-1 bis B 0-700) entsprechen. corresponding to compounds B10-1 to B 0-700).
B1 1 . Verbindungen B11 -1 bis B11 -700 der allgemeinen Formel (I), worin R1 und R2 für Wasserstoff stehen, R3 für Chlor steht, X für O steht und Q, W, Z1, Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; B1 1. Compounds B11 -1 to B11 -700 of the general formula (I) in which R 1 and R 2 are hydrogen, R 3 is chlorine, X is O and Q, W, Z 1 , Z 2 for each individual compound in Table 2 remainder definitions (Nos 1 to 700;
entsprechend Verbindungen B1 1 -1 bis B1 1 -700) entsprechen. corresponding to compounds B1 1 -1 to B1 1 -700).
B12. Verbindungen B12-1 bis B12-700 der allgemeinen Formel (I), worin R2 und R3 für Wasserstoff stehen, R1 für Fluor steht, X für O steht und Q, W, Z1, Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; B12. Compounds B12-1 to B12-700 of the general formula (I) in which R 2 and R 3 are hydrogen, R 1 is fluorine, X is O and Q, W, Z 1 , Z 2 for each individual compound in Table 2 remainder definitions (Nos 1 to 700;
entsprechend Verbindungen B12-1 bis B12-700) entsprechen. corresponding to compounds B12-1 to B12-700).
B13. Verbindungen B13-1 bis B13-700 der allgemeinen Formel (I), worin R2 und R3 für Wasserstoff stehen, R1 für Chlor steht, X für O steht und Q, W, Z1, Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; B13. Compounds B13-1 to B13-700 of the general formula (I) in which R 2 and R 3 are hydrogen, R 1 is chlorine, X is O and Q, W, Z 1 , Z 2 for each individual compound in Table 2 remainder definitions (Nos 1 to 700;
entsprechend Verbindungen B13-1 bis B13-700) entsprechen. corresponding to compounds B13-1 to B13-700).
C1 . Verbindungen C1 -1 bis C1-700 der allgemeinen Formel (I), worin R\ R2 und R3 für Wasserstoff stehen und Q, W, Z\ Z2 den Definitionen (Nos 1 bis 700; entsprechend Verbindungen C1 -1 bis C1 -700) in der oben aufgeführten Tabelle 2 entsprechen. C1. Compounds C1-1 to C1-700 of the general formula (I) in which R \ R 2 and R 3 are hydrogen and Q, W, Z \ Z 2 are the definitions (Nos 1 to 700, corresponding to compounds C1 to C1 -700) in Table 2 above.
C2. Verbindungen C2-1 bis C2-700 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Fluor steht, X für S steht und Q, W, Z1, Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; C2. Compounds C2-1 to C2-700 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is fluorine, X is S and Q, W, Z 1 , Z 2 for each individual compound in Table 2 remainder definitions (Nos 1 to 700;
entsprechend Verbindungen C2-1 bis C2-700) entsprechen. corresponding to compounds C2-1 to C2-700).
C3. Verbindungen C3-1 bis C3-700 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Chlor steht, X für S steht und Q, W, Z1, Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; C3. Compounds C3-1 to C3-700 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is chlorine, X is S and Q, W, Z 1 , Z 2 for each individual compound in Table 2 remainder definitions (Nos 1 to 700;
entsprechend Verbindungen C3-1 bis C3-700) entsprechen. corresponding to compounds C3-1 to C3-700).
C4. Verbindungen C4-1 bis C4-700 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Brom steht, X für S steht und Q, W, Z1, Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; C4. Compounds C4-1 to C4-700 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is bromine, X is S and Q, W, Z 1 , Z 2 for each individual compound in Table 2 remainder definitions (Nos 1 to 700;
entsprechend Verbindungen C4-1 bis C4-700) entsprechen. corresponding to compounds C4-1 to C4-700).
C5. Verbindungen C5-1 bis C5-700 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für lod steht, X für S steht und Q, W, Z1, Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; C5. Compounds C5-1 to C5-700 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is iodine, X is S and Q, W, Z 1 , Z 2 for each individual compound in Table 2 remainder definitions (Nos 1 to 700;
entsprechend Verbindungen C5-1 bis C5-700) entsprechen. corresponding to compounds C5-1 to C5-700).
C6. Verbindungen C6-1 bis C6-700 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Trifluormethyl steht, X für S steht und Q, W, Z1, Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; entsprechend Verbindungen C6-1 bis C6-700) entsprechen. C6. Compounds C6-1 to C6-700 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is trifluoromethyl, X is S and Q, W, Z 1 , Z 2 for each individual compound in Table 2, the residue definitions (Nos 1 to 700, corresponding to compounds C6-1 to C6-700).
C7. Verbindungen C7-1 bis C7-700 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Methyl steht, X für S steht und Q, W, Z\ Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; C7. Compounds C7-1 to C7-700 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is methyl, X is S and Q, W, Z \ Z 2 for the particular individual compound denoted in Table 2 referred to residue definitions (Nos 1 to 700;
entsprechend Verbindungen C7-1 bis C7-700) entsprechen. corresponding to compounds C7-1 to C7-700).
C8. Verbindungen C8-1 bis C8-700 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Methoxy steht, X für S steht und Q, W, Z1, Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; entsprechend Verbindungen C8-1 bis C8-700) entsprechen. C8. Compounds C8-1 to C8-700 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is methoxy, X is S and Q, W, Z 1 , Z 2 for the respective individual compound correspond to the radical definitions given in Table 2 (Nos 1 to 700, corresponding to compounds C8-1 to C8-700).
C9. Verbindungen C9-1 bis C9-700 der allgemeinen Formel (I), worin R1 und R3 für Wasserstoff stehen, R2 für Trifluormethoxy steht, X für S steht und Q, W, Z1 , Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; entsprechend Verbindungen C8-1 bis C8-700) entsprechen. C9. Compounds C9-1 to C9-700 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is trifluoromethoxy, X is S and Q, W, Z 1 , Z 2 for each individual compound in Table 2, the remaining definitions (Nos 1 to 700, corresponding to compounds C8-1 to C8-700).
C10. Verbindungen C10-1 bis C10-700 der allgemeinen Formel (I), worin R1 und R2 für Wasserstoff stehen, R3 für Fluor steht, X für S steht und Q, W, Z1 , Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; C10. Compounds C10-1 to C10-700 of the general formula (I) in which R 1 and R 2 are hydrogen, R 3 is fluorine, X is S and Q, W, Z 1 , Z 2 for each individual compound in Table 2 remainder definitions (Nos 1 to 700;
entsprechend Verbindungen C10-1 bis C10-700) entsprechen. according to compounds C10-1 to C10-700).
C1 1 . Verbindungen C1 1 -1 bis C1 1 -700 der allgemeinen Formel (I), worin R1 und R2 für Wasserstoff stehen, R3 für Chlor steht, X für S steht und Q, W, Z Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; C1 1. Compounds C1 1 -1 to C1 1-700 of the general formula (I) in which R 1 and R 2 are hydrogen, R 3 is chlorine, X is S and Q, W, ZZ 2 for each individual compound denote in Table 2 referred to residue definitions (Nos 1 to 700;
entsprechend Verbindungen C1 1 -1 bis C1 1 -700) entsprechen. corresponding to compounds C1 1 -1 to C1 1 -700).
C12. Verbindungen C12-1 bis C12-700 der allgemeinen Formel (I), worin R2 und R3 für Wasserstoff stehen, R1 für Fluor steht, X für S steht und Q, W, Z1 , Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; C12. Compounds C12-1 to C12-700 of the general formula (I) in which R 2 and R 3 are hydrogen, R 1 is fluorine, X is S and Q, W, Z 1 , Z 2 for each individual compound in Table 2 remainder definitions (Nos 1 to 700;
entsprechend Verbindungen C12-1 bis C12-700) entsprechen. corresponding to compounds C12-1 to C12-700).
C13. Verbindungen C13-1 bis C13-700 der allgemeinen Formel (I), worin R2 und R3 für Wasserstoff stehen, R1 für Chlor steht, X für S steht und Q, W, Z\ Z2 für die jeweilige Einzelverbindung den in Tabelle 2 genannten Restedefinitionen (Nos 1 bis 700; C13. Compounds C13-1 to C13-700 of the general formula (I) in which R 2 and R 3 are hydrogen, R 1 is chlorine, X is S and Q, W, Z \ Z 2 for the particular individual compound denoted in Table 2 referred to residue definitions (Nos 1 to 700;
entsprechend Verbindungen C13-1 bis C13-700) entsprechen. corresponding to compounds C13-1 to C13-700).
Spektroskopische Daten ausgewählter Tabellenbeispiele: Spectroscopic data of selected table examples:
Beispiel No. A1 -2: Example No. A1 -2:
1 H-NMR (400 MHz, de-DMSO δ, ppm) 13.02 (s, 1 H, NH), 9.43 (d, 1 H, NH), 8.05 (d, 2H), 7.71 (d, 1 H, NH), 7.62 (d, 1 H), 7.23 (t, 1 H), 6.83 (d, 2H), 3.02 (s, 6H). Beispie! No. A1-3: 1 H-NMR (400 MHz, de-DMSO δ, ppm) 13.02 (s, 1H, NH), 9.43 (d, 1H, NH), 8.05 (d, 2H), 7.71 (d, 1H, NH ), 7.62 (d, 1H), 7.23 (t, 1H), 6.83 (d, 2H), 3.02 (s, 6H). Step Example! No. A1-3:
1H-NMR (400 MHz, de-DMSO δ, ppm) 13.11 (s, 1H, NH), 10.12 (d, 1H), 9.40 (d, 1H, NH), 8.08 (d, 2H), 7.82 (d, 1H,), 7.72 (d, 1H, NH), 7.68 (d, 1H), 7.29 (t, 1H), 6.95 (d, 2H). 1 H-NMR (400 MHz, de-DMSO δ, ppm) 13.11 (s, 1H, NH), 10.12 (d, 1H), 9.40 (d, 1H, NH), 8.08 (d, 2H), 7.82 (i.e. , 1H,), 7.72 (d, 1H, NH), 7.68 (d, 1H), 7.29 (t, 1H), 6.95 (d, 2H).
Beispiel No. A1-4: Example No. A1-4:
1H-NMR (400 MHz, de-DMSO δ, ppm) 13.65 (s, 1H, NH), 9.27 (d, 2H), 8.67 (d, 1H), 7.91 (d, 1H), 7.80 (m, 3H), 7.40 (t, 1H). 1 H-NMR (400 MHz, de-DMSO δ, ppm) 13.65 (s, 1H, NH), 9.27 (d, 2H), 8.67 (d, 1H), 7.91 (d, 1H), 7.80 (m, 3H ), 7.40 (t, 1H).
Beispiel No. A1-5: Example No. A1-5:
1H-NMR (400 MHz, de-DMSO δ, ppm) 13.63 (s, 1H, NH), 9.31 (d, 1H, NH), 8.43 (d, 2H), 8.02 (d, 2H), 7.85 (m, 3H), 7.41 (t, 1H). Beispiel No. A1-6: 1 H-NMR (400 MHz, de-DMSO δ, ppm) 13.63 (s, 1H, NH), 9.31 (d, 1H, NH), 8.43 (d, 2H), 8.02 (d, 2H), 7.85 (m , 3H), 7.41 (t, 1H). Example No. A1-6:
1H-NMR (400 MHz, de-DMSO δ, ppm) 13.83 (s, 1H, NH), 9.61 (s, 1H), 9.23 (s, 1H), 8.88 (d, 1H), 8.16 (d, 1H), 7.93 (d, 1H), 7.84 (m, 2H), 7.45 (t, 1H). 1 H-NMR (400 MHz, de-DMSO δ, ppm) 13.83 (s, 1H, NH), 9.61 (s, 1H), 9.23 (s, 1H), 8.88 (d, 1H), 8.16 (d, 1H ), 7.93 (d, 1H), 7.84 (m, 2H), 7.45 (t, 1H).
Beispiel No. A1-7: Example No. A1-7:
1H-NMR (400 MHz, de-DMSO δ, ppm) 13.52 (s, 1H, NH), 9.23 (d, 1H, NH), 8.38 (d, 2H), 7.90 (d, 1H), 7.82 (d, 1H, NH), 7.78 (d, 1H), 7.6 (d, 2H), 7.38 (t, 1H). 1H-NMR (400 MHz, de-DMSO δ, ppm) 13.52 (s, 1H, NH), 9.23 (d, 1H, NH), 8.38 (d, 2H), 7.90 (d, 1H), 7.82 (d, 1H, NH), 7.78 (d, 1H), 7.6 (d, 2H), 7.38 (t, 1H).
Beispiel No. A1-8: Example No. A1-8:
1H-NMR (400 MHz, CDCb δ, ppm) 9.85 (br. s, 1H, NH), 9.71 (br. s, 1H, NH), 8.2 (d, 1 H), 8.02 (m, 2H), 7.65 (d, 1 H), 7.49 (m, 3H), 5.95 (br. s, 1 H). 1 H-NMR (400 MHz, CDCb δ, ppm) 9.85 (br.s, 1H, NH), 9.71 (br.s, 1H, NH), 8.2 (d, 1H), 8.02 (m, 2H), 7.65 (d, 1H), 7.49 (m, 3H), 5.95 (br. S, 1H).
Beispiel No. A1-9: Example No. A1-9:
1H-NMR (400 MHz, de-DMSO δ, ppm) 13.10 (s, 1H, NH), 9.25 (s, 1H), 8.38 (m, 1H), 7.90 (d, 1H), 7.75 (m, 2H), 7.55 (m, 1H), 7.35 (m, 2H). 1 H-NMR (400 MHz, de-DMSO δ, ppm) 13.10 (s, 1H, NH), 9.25 (s, 1H), 8.38 (m, 1H), 7.90 (d, 1H), 7.75 (m, 2H ), 7.55 (m, 1H), 7.35 (m, 2H).
Beispiel No. A1-10: Example No. A1-10:
1H-NMR (400 MHz, de-DMSO δ, ppm) 13.55 (s, 1H, NH), 9.21 (s, 1H, NH), 8.49 (s, 1H), 8.25 (d, 1H), 7.85 (m, 2H), 7.75 (m, 1H), 7.42 (t, 1H). Beispie! No. A1-11: 1 H-NMR (400 MHz, de-DMSO δ, ppm) 13.55 (s, 1H, NH), 9.21 (s, 1H, NH), 8.49 (s, 1H), 8.25 (d, 1H), 7.85 (m , 2H), 7.75 (m, 1H), 7.42 (t, 1H). Step Example! No. A1-11:
1H-NMR (400 MHz, de-DMSO δ, ppm) 9.31 (s, 1H), 8.40 (t, 1H), 7.95 (d, 1H), 7.83 (m, 2H), 7.61 (d, 1H), 7.42 (m, 3H). 1 H-NMR (400 MHz, de-DMSO δ, ppm) 9.31 (s, 1H), 8.40 (t, 1H), 7.95 (d, 1H), 7.83 (m, 2H), 7.61 (d, 1H), 7.42 (m, 3H).
Beispiel No. A1-12: Example No. A1-12:
1H-NMR (400 MHz, de-DMSO δ, ppm) 13.10 (s, 1H, NH), 9.24 (s, 1H, NH), 8.38 (m, 1H), 7.91 (d, 1H), 7.82 (m, 2H), 7.75 (m, 1H), 7.35 (m, 2H). Beispiel No. A1-14: 1 H-NMR (400 MHz, de-DMSO δ, ppm) 13.10 (s, 1H, NH), 9.24 (s, 1H, NH), 8.38 (m, 1H), 7.91 (d, 1H), 7.82 (m , 2H), 7.75 (m, 1H), 7.35 (m, 2H). Example No. A1-14:
1H-NMR (400 MHz, de-DMSO δ, ppm) 13.48 (s, 1H, NH), 9.28 (s, 1H, NH), 8.23 (d, 2H), 7,89 (d, 1H), 7.80 (m, 4H), 7.37 (t, 1H). 1 H-NMR (400 MHz, de-DMSO δ, ppm) 13.48 (s, 1H, NH), 9.28 (s, 1H, NH), 8.23 (d, 2H), 7.89 (d, 1H), 7.80 (m, 4H), 7.37 (t, 1H).
Beispiel No. A1-15: Example No. A1-15:
1H-NMR (400 MHz, de-DMSO δ, ppm) 13.75 (br. s, 1H, NH), 9.24 (br. s, 1H, NH), 8.31 (d, 2H), 8.22 (d, 2H), 7,92 (d, 1H), 7.80 (m, 2H), 7.44 (t, 1H). 1H-NMR (400 MHz, de-DMSO δ, ppm) 13.75 (br.s, 1H, NH), 9.24 (br.s, 1H, NH), 8.31 (d, 2H), 8.22 (d, 2H), 7.92 (d, 1H), 7.80 (m, 2H), 7.44 (t, 1H).
Beispiel No. A1-16: Example No. A1-16:
1H-NMR (400 MHz, de-DMSO δ, ppm) 8.30 (d, 1H, NH), 7.9 (d, 1H), 7.80 (d, 1H), 7,35 (m, 2H), 7.10 (d, 1H), 7.00 (t, 1H). 1 H-NMR (400 MHz, de-DMSO δ, ppm) 8.30 (d, 1H, NH), 7.9 (d, 1H), 7.80 (d, 1H), 7.35 (m, 2H), 7.10 (i.e. , 1H), 7.00 (t, 1H).
Beispiel No. A1-17: Example No. A1-17:
1H-NMR (400 MHz, CD3OD δ, ppm) 7.82 (d, 1H), 7.75 (d, 1H), 7.68 (s, 1H), 7.55 (d, 1H), 7.25 (t, 1H), 6.85 (d, 1H), 3.90 (s, 3H). 1 H-NMR (400 MHz, CD 3 OD δ, ppm) 7.82 (d, 1H), 7.75 (d, 1H), 7.68 (s, 1H), 7:55 (d, 1H), 7.25 (t, 1H), 6.85 (d, 1H), 3.90 (s, 3H).
Beispiel No. A1-76: Example No. A1-76:
1H-NMR (400 MHz, de-DMSO δ, ppm) 12.65 (s, 1H, NH), 9.37 (d, 1H, NH), 7.8 (d, 1H), 7.68 (br. s, 1H, NH), 7.62 (d, 1H), 7.25 (t, 1H), 3.22 (m, 1H), 1.39 (d, 6H). Beispiel No. A1-77: 1 H-NMR (400 MHz, de-DMSO δ, ppm) 12.65 (s, 1H, NH), 9.37 (d, 1H, NH), 7.8 (d, 1H), 7.68 (br, s, 1H, NH) , 7.62 (d, 1H), 7.25 (t, 1H), 3.22 (m, 1H), 1.39 (d, 6H). Example No. A1-77:
1H-NMR (400 MHz, de-DMSO δ, ppm) 12.6 (s, 1H, NH), 9.4 (d, 1H, NH), 7.8 (d, 1H), 7.68 (br. s, 1H, NH), 7.62 (d, 1H), 7.26 (t, 1H), 1.43 (s, 9H). Beispie! No. A1-78: 1 H-NMR (400 MHz, de-DMSO δ, ppm) 12.6 (s, 1H, NH), 9.4 (d, 1H, NH), 7.8 (d, 1H), 7.68 (br, s, 1H, NH) , 7.62 (d, 1H), 7.26 (t, 1H), 1.43 (s, 9H). Step Example! No. A1-78:
1H-NMR (400 MHz, CDCb δ, ppm) 9.90 (br. s, 1H, NH), 8.10 (s, 1H), 7.55 (s, 1H), 7.27 (t, 1H), 5.94 (br. s, 1H, NH), 2.80 (m, 1H), 1.85 (m, 4H), 0.90 (t, 6H). Beispiel No. A1-79: 1 H-NMR (400 MHz, CDCb δ, ppm) 9.90 (br.s, 1H, NH), 8.10 (s, 1H), 7.55 (s, 1H), 7.27 (t, 1H), 5.94 (br , 1H, NH), 2.80 (m, 1H), 1.85 (m, 4H), 0.90 (t, 6H). Example No. A1-79:
1H-NMR (400 MHz, CD3OD δ, ppm) 7.74 (d, 1H), 7.48 (d, 1H), 7.13 (t, 1H), 2.10 (s, 1H), 1.08 (d, 4H). 1 H-NMR (400 MHz, CD 3 OD δ, ppm) 7.74 (d, 1H), 7:48 (d, 1H), 7.13 (t, 1H), 2.10 (s, 1H) 1.08 (d, 4H).
Beispiel No. A1-81: Example No. A1-81:
1H-NMR (400 MHz, CDCh δ, ppm) 9.60 (br. s, 1H, NH), 8.10 (s, 1H), 7.60 (s, 1H), 7.25 (t, 1H), 5.90 (br. s, 1H, NH), 3.35 (m, 1H), 2.20 (m, 2H), 2.00 (m, 2H), 1.85 (m, 2H), 1.73 (m, 2H). 1H-NMR (400 MHz, CDCh δ, ppm) 9.60 (br.s, 1H, NH), 8.10 (s, 1H), 7.60 (s, 1H), 7.25 (t, 1H), 5.90 (br. 1H, NH), 3.35 (m, 1H), 2.20 (m, 2H), 2.00 (m, 2H), 1.85 (m, 2H), 1.73 (m, 2H).
Beispiel No. A1-82: Example No. A1-82:
1H-NMR (400 MHz, de-DMSO δ, ppm) 12.6 (s, 1H, NH), 9.35 (d, 1H, NH), 7.8 (d, 1H), 7.62 (m, 2H), 7.25 (t, 1H), 2.9 (m, 1H), 2.07 (d, 2H), 1.8 (m, 2H), 1.7-1.55 (m, 3H), 1.43-1.23 (m, 3H). 1H-NMR (400 MHz, de-DMSO δ, ppm) 12.6 (s, 1H, NH), 9.35 (d, 1H, NH), 7.8 (d, 1H), 7.62 (m, 2H), 7.25 (t, 1H), 2.9 (m, 1H), 2.07 (d, 2H), 1.8 (m, 2H), 1.7-1.55 (m, 3H), 1.43-1.23 (m, 3H).
Beispiel No. A1-177: Example No. A1-177:
1H-NMR (400 MHz, CD3OD δ, ppm) 7.90 (d, 1 H), 7.70 (d, 1 H), 7.30 (t, 1 H), 3.44 (d,1H-NMR (400 MHz, CD3OD δ, ppm) 7.90 (d, 1H), 7.70 (d, 1H), 7.30 (t, 1H), 3.44 (d,
2H), 3.24 (m, 1H), 2.80 (t, 2H), 2.70 (d, 2H), 2.35 - 2.20 (m, 4H), 2.10 (m, 1H), 1.04 (d, 6H). 2H), 3.24 (m, 1H), 2.80 (t, 2H), 2.70 (d, 2H), 2.35 - 2.20 (m, 4H), 2.10 (m, 1H), 1.04 (d, 6H).
Beispiel No. A1-208: Example No. A1-208:
1H-NMR (400 MHz, CDC δ, ppm) 9.65 (br. s, 1 H, NH), 8.95 (br. s, 1 H, NH), 8.10 (d, 1H), 7.90 (d, 1H), 7.52 (t, 1H), 7.35 - 7.20 (m, 5H), 2.95 (m, 2H), 2.77 (t, 2H), 2.23 (m, 2H). 1H-NMR (400 MHz, CDC δ, ppm) 9.65 (br.s, 1H, NH), 8.95 (br.s, 1H, NH), 8.10 (d, 1H), 7.90 (d, 1H), 7.52 (t, 1H), 7.35 - 7.20 (m, 5H), 2.95 (m, 2H), 2.77 (t, 2H), 2.23 (m, 2H).
Beispiel No. A1-227: Example No. A1-227:
1H-NMR (400 MHz, CD3OD δ, ppm) 8.30 (s, 1H), 7.95 (d, 1H), 7.70 (d, 1H), 7.35 (t, 1H), 4.03 (s, 3H). Beispie! No. A1-228: 1H-NMR (400 MHz, CD3OD δ, ppm) 8.30 (s, 1H), 7.95 (d, 1H), 7.70 (d, 1H), 7.35 (t, 1H), 4.03 (s, 3H). Step Example! No. A1-228:
1H-NMR (400 MHz, CD3OD δ, ppm) 8.27 (s, 1H), 7.95 (d, 1H), 7.70 (d, 1H), 7.50 + 6.90 (s, 1H), 7.30 (t, 1H), 4.03 (s, 3H). Beispiel No. A1-491: 1 H-NMR (δ 400 MHz, CD 3 OD, ppm) 8.27 (s, 1H), 7.95 (d, 1H), 7.70 (d, 1H), 7.50 + 6.90 (s, 1H), 7.30 (t, 1H ), 4.03 (s, 3H). Example No. A1-491:
1H-NMR (400 MHz, CDCb δ, ppm) 9.65 (br. s, 1H, NH), 8.08 (d, 1H), 7.45 (d, 1H), 7.3 (t, 1H), 5.89 (br. s, 1H, NH), 4.2 (d, 2H), 2.04 (m, 1H), 1.3 (m, 3H), 1.18 (m, 2H), 0.63 (m, 2H), 0.44 (m, 2H). Beispiel No. A2-76: 1 H-NMR (400 MHz, CDCb δ, ppm) 9.65 (br.s, 1H, NH), 8.08 (d, 1H), 7.45 (d, 1H), 7.3 (t, 1H), 5.89 (br , 1H, NH), 4.2 (d, 2H), 2.04 (m, 1H), 1.3 (m, 3H), 1.18 (m, 2H), 0.63 (m, 2H), 0.44 (m, 2H). Example No. A2-76:
1H-NMR (400 MHz, CDCb δ, ppm) 9.70 (br. s, 1H, NH), 8.40 (s, 1H), 8.15 + 7.65 (br. s, 1H, NH), 7.80 (s, 1H), 6.00 (br. s, 2H), 3.30 (m, 1H), 1.60 (d, 6H). 1 H-NMR (400 MHz, CDCb δ, ppm) 9.70 (br.s, 1H, NH), 8.40 (s, 1H), 8.15 + 7.65 (br.s, 1H, NH), 7.80 (s, 1H) , 6.00 (br s, 2H), 3.30 (m, 1H), 1.60 (d, 6H).
Beispiel No. A2-81: Example No. A2-81:
1H-NMR (400 MHz, de-DMSO δ, ppm) 13.25 (s, 1H, NH), 8.25 (s, 1H, NH), 8.08 (d, 2H), 3.40 (m, 1H), 2.12 (m, 2H), 1.94 (m, 2H), 1.75 (m, 2H) 1.70 (m, 2H). 1H-NMR (400 MHz, de-DMSO δ, ppm) 13.25 (s, 1H, NH), 8.25 (s, 1H, NH), 8.08 (d, 2H), 3.40 (m, 1H), 2.12 (m, 2H), 1.94 (m, 2H), 1.75 (m, 2H) 1.70 (m, 2H).
Beispiel No. A2-82: Example No. A2-82:
1H-NMR (400 MHz, CDCb δ, ppm) 9.70 (br. s, 1H, NH), 8.40 (s, 1H), 8.15 + 7.65 (br. s, 1H, NH), 7.80 (s, 1H), 6.00 (br. s, 1H), 3.30 (m, 1H), 2.20 (m, 2H), 1.90 (m, 2H), 1.80 (m, 1H).1.70 (m, 2H), 1.50 (m, 2H), 1.40 (m, 1H). 1 H-NMR (400 MHz, CDCb δ, ppm) 9.70 (br.s, 1H, NH), 8.40 (s, 1H), 8.15 + 7.65 (br.s, 1H, NH), 7.80 (s, 1H) , 6.00 (brs s, 1H), 3.30 (m, 1H), 2.20 (m, 2H), 1.90 (m, 2H), 1.80 (m, 1H) .1.70 (m, 2H), 1.50 (m, 2H ), 1.40 (m, 1H).
Beispiel No. B1-5: Example No. B1-5:
1H-NMR (400 MHz, CDCI3 δ, ppm) 8.85 (br. s, 1H, NH), 8.42 (d, 1H), 8.25 (d, 1H), 7.84 (d, 2H), 7.79 (d, 1H), 7.53 (t, 1H), 5.92 (br. s, 1H, NH). 1 H-NMR (400 MHz, CDCl3 δ, ppm) 8.85 (br. S, 1H, NH), 8.42 (d, 1H), 8.25 (d, 1H), 7.84 (d, 2H), 7.79 (d, 1H ), 7.53 (t, 1H), 5.92 (brs s, 1H, NH).
Beispiel No. B1-7: Example No. B1-7:
1H-NMR (400 MHz, DMSO-de δ, ppm) 8.48-8.43 (m, 2H), 8.01-7.98 (m, 2H), 7.67-7.53 (m, 3H), 7.49 (t, 1H). 1 H-NMR (400 MHz, DMSO-de δ, ppm) 8.48-8.43 (m, 2H), 8.01-7.98 (m, 2H), 7.67-7.53 (m, 3H), 7.49 (t, 1H).
Beispiel No. B1-8: Example No. B1-8:
1H-NMR (400 MHz, DMSO-de δ, ppm) 8.43 (br. s, 1H), 8.32 (d, 2H), 8.01-7.97 (m, 3H), 7.72-7.68 (d, 2H), 7.56 (t, 1H) Beispie! No. B1-11: 1 H-NMR (400 MHz, DMSO-de δ, ppm) 8.43 (br.s, 1H), 8.32 (d, 2H), 8.01-7.97 (m, 3H), 7.72-7.68 (d, 2H), 7.56 (t, 1H) Step Example! No. B1-11:
1H-NMR (400 MHz, DMSO-de δ, ppm) 8.43-8.39 (m, 2H), 8.07-8.00 (m, 3H), 7.81 (d, 1H), 7.62-7.57 (m, 2H) 1 H-NMR (400 MHz, DMSO-de δ, ppm) 8.43-8.39 (m, 2H), 8.07-8.00 (m, 3H), 7.81 (d, 1H), 7.62-7.57 (m, 2H)
Beispiel No. B1-14: Example No. B1-14:
1H-NMR (400 MHz, DMSO-de δ, ppm) 8.45 (br. s, 1H), 8.23 (d, 2H), 8.03-7.99 (m, 3H), 7.86 (d, 2H), 7.57 (t, 1H). Beispie! No. B1-36: 1 H-NMR (400 MHz, DMSO-de δ, ppm) 8.45 (br.s, 1H), 8.23 (d, 2H), 8.03-7.99 (m, 3H), 7.86 (d, 2H), 7.57 (t , 1H). Step Example! No. B1-36:
1H-NMR (400 MHz, DMSO-de δ, ppm) 8.38 (br. s, 1H), 8.25 (d, 1H), 8.09-7.96 (m, 4H), 7.66-7.61 (m, 2H). 1 H-NMR (400 MHz, DMSO-de δ, ppm) 8.38 (br.s, 1H), 8.25 (d, 1H), 8.09-7.96 (m, 4H), 7.66-7.61 (m, 2H).
Beispie! No. B1-50: Step Example! No. B1-50:
1H-NMR (400 MHz, DMSO-de δ, ppm) 8.49 (br. s, 1H, NH), 8.24 (d, 2H), 7.99-7.94 (m, 3H), 7.50 (t, 1H), 7.18 (d, 2H), 3.88 (s, 3H). 1H-NMR (400 MHz, DMSO-de δ, ppm) 8.49 (br.s, 1H, NH), 8.24 (d, 2H), 7.99-7.94 (m, 3H), 7.50 (t, 1H), 7.18 ( d, 2H), 3.88 (s, 3H).
Beispie! No. B1-75: Step Example! No. B1-75:
1H-NMR (400 MHz, DMSO-de δ, ppm) 8.31 (br. s, 1 H), 8.06 (d, 1 H), 7.90-7.84 (m, 2H), 7.51 (t, 1H), 2.70 (s, 3H). 1 H-NMR (400 MHz, DMSO-de δ, ppm) 8.31 (br.s, 1H), 8.06 (d, 1H), 7.90-7.84 (m, 2H), 7.51 (t, 1H), 2.70 (s, 3H).
Beispie! No. B1-76: Step Example! No. B1-76:
1H-NMR (400 MHz, CDCh δ, ppm) 8.90 (br. s, 1H, NH), 8.13 (d, 1H), 7.63 (d, 1H), 7.40 (t, 1H), 5.85 (br. s, 1H, NH), 3.29 (m, 1H), 1.49 (d, 6H). 1 H-NMR (400 MHz, CDCh δ, ppm) 8.90 (br.s, 1H, NH), 8.13 (d, 1H), 7.63 (d, 1H), 7.40 (t, 1H), 5.85 (br , 1H, NH), 3.29 (m, 1H), 1.49 (d, 6H).
Beispiel No. B1-77: Example No. B1-77:
1H-NMR (400 MHz, CDCh δ, ppm) 8.94 (br. s, 1H, NH), 8.25 (d, 1H), 7.65 (d, 1H), 7.41 (t, 1H), 5.82 (br. s, 1H, NH), 1.53 (s, 9H). Beispiel No. B1-82: 1 H-NMR (400 MHz, CDCh δ, ppm) 8.94 (br.s, 1H, NH), 8.25 (d, 1H), 7.65 (d, 1H), 7.41 (t, 1H), 5.82 (br , 1H, NH), 1.53 (s, 9H). Example No. B1-82:
1H-NMR (400 MHz, CDCh δ, ppm) 8.90 (br. s, 1H, NH), 8.13 (d, 1H), 7.63 (d, 1H), 7.40 (t, 1H), 5.83 (br. s, 1H, NH), 3.0(m, 1H), 2.20 (m, 2H), 1.90 (m, 2H), 1.75-1.65 (m, 3H), 1.45-1.30 (m, 3H). Beispiel No. B1-328: 1 H-NMR (400 MHz, CDCh δ, ppm) 8.90 (br.s, 1H, NH), 8.13 (d, 1H), 7.63 (d, 1H), 7.40 (t, 1H), 5.83 (br , 1H, NH), 3.0 (m, 1H), 2.20 (m, 2H), 1.90 (m, 2H), 1.75-1.65 (m, 3H), 1.45-1.30 (m, 3H). Example No. B1-328:
1H-NMR (400 MHz, CDCb δ, ppm) 10.12 (br. s, 1 H, NH), 7.83 (d, 1 H), 7.54 (t, 1 H), 7.40 (d, 1 H), 7.19 (br. s, 1 H, NH). 1 H-NMR (400 MHz, CDCb δ, ppm) 10.12 (brs s, 1H, NH), 7.83 (d, 1H), 7.54 (t, 1H), 7.40 (d, 1H), 7.19 (br s, 1H, NH).
Beispiel No. B1-331 : Example No. B1-331:
1H-NMR (400 MHz, CDCb δ, ppm) 9.50 (br. s, 1 H, NH), 7.82 (d, 1 H), 7.57 (m, 1 H), 7.40 (d, 1 H), 7.13 (br. s, 1 H, NH). Beispiel No. C1-328: 1 H-NMR (400 MHz, CDCb δ, ppm) 9.50 (br.s, 1H, NH), 7.82 (d, 1H), 7.57 (m, 1H), 7.40 (d, 1H), 7.13 (br s, 1H, NH). Example No. C1-328:
1H-NMR (400 MHz, CDCb δ, ppm) 9.18 (br. s, 1 H, NH), 8.60 (d, 1 H), 8.18 (d, 1 H), 7.74 (t, 1 H), 6.03 (br. s, 1 H, NH). 1 H-NMR (400 MHz, CDCb δ, ppm) 9.18 (br, s, 1H, NH), 8.60 (d, 1H), 8.18 (d, 1H), 7.74 (t, 1H), 6.03 (br s, 1H, NH).
Gegenstand der vorliegenden Erfindung ist somit die Verwendung mindestens einer Verbindung, ausgewählt aus der Gruppe, bestehend aus substituierten 2-The present invention thus provides the use of at least one compound selected from the group consisting of substituted
Amidobenzimidazolen, 2-Amidobenzoxazolen und 2-Amidobenzothiazolen der allgemeinen Formel (I), sowie von beliebigen Mischungen dieser erfindungsgemäßen substituierten 2-Amidobenzimidazole, 2-Amidobenzoxazole und 2-Amidobenzothiazole der allgemeinen Formel (I) mit weiteren agrochemischen Wirkstoffen, zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren, bevorzugt Trockenstress, sowie zur Stärkung des Pflanzenwachstums und/oder zur Erhöhung des Pflanzenertrags. Amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles of the general formula (I), and of any desired mixtures of these substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles of the general formula (I) according to the invention with other agrochemical active compounds to increase the resistance of Plants against abiotic stress factors, preferably drought stress, as well as to enhance plant growth and / or increase the plant yield.
Weiterer Gegenstand der vorliegenden Erfindung ist eine Sprühlösung zur Behandlung von Pflanzen, enthaltend eine zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren wirksame Menge von mindestens einer A further subject of the present invention is a spray solution for the treatment of plants, comprising an amount of at least one effective for increasing the resistance of plants to abiotic stress factors
Verbindung, ausgewählt aus der Gruppe, bestehend aus substituierten 2- Amidobenzimidazolen, 2-Amidobenzoxazolen und 2-Amidobenzothiazolen, der allgemeinen Formel (I). Zu den dabei relativierbaren abiotischen Stressbedingungen können zum Beispiel Hitze, Dürre, Kälte- und Trockenstress (Stress verursacht durch Trockenheit und/oder Wassenmangel), osmotischer Streß, Staunässe, erhöhter Bodensalzgehalt, erhöhtes Ausgesetztsein an Mineralien, Ozonbedingungen, Starklichtbedingungen, beschränkte Verfügbarkeit von Stickstoffnährstoffen, beschränkte Verfügbarkeit von Phosphornährstoffen zählen. A compound selected from the group consisting of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles, of general formula (I). For example, heat, drought, cold and drought stress (stress caused by drought and / or water deficiency), osmotic stress, waterlogging, increased soil salt content, increased exposure to minerals, ozone conditions, High light conditions, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients.
In einer Ausführungsform kann beispielsweise vorgesehen sein, dass die For example, in one embodiment, it may be provided that the
erfindungsgemäß vorgesehenen Verbindungen, d. h. die entsprechenden Compounds provided according to the invention, d. H. the corresponding
substituierten 2-Amidobenzimidazole, 2-Amidobenzoxazole und 2-Amidobenzothiazole der allgemeinen Formel (!), durch eine Sprühapplikation auf entsprechende zu behandelnde Pflanzen oder Pflanzenteile aufgebracht werden. Die erfindungsgemäß vorgesehene Verwendung der Verbindungen der allgemeinen Formel (I) oder deren Salze erfolgt vorzugsweise mit einer Dosierung zwischen 0,00005 und 3 kg/ha, besonders bevorzugt zwischen 0,0001 und 2 kg/ha, insbesondere bevorzugt zwischen 0,0005 und 1 kg/ha, im Speziellen bevorzugt zwischen 0,001 und 0,25 kg/ha. Wenn im Rahmen der vorliegenden Erfindung Abscisinsäure gleichzeitig mit substituierten 2- Amidobenzimidazolen, 2-Amidobenzoxazolen und 2-Amidobenzothiazolen der allgemeinen Formel (I), beispielsweise in Rahmen einer gemeinsamen Zubereitung oder Formulierung verwendet wird, so erfolgt die Zumischung von Abscisinsäure dabei vorzugsweise in einer Dosierung zwischen 0.0001 und 3 kg/ha, besonders bevorzugt zwischen 0.001 und 2 kg/ha, insbesondere bevorzugt zwischen 0.005 und 1 kg/ha, im Speziellen bevorzugt zwischen 0.006 und 0.25 kg/ha. Substituted 2-Amidobenzimidazole, 2-Amidobenzoxazole and 2-amidobenzothiazoles of the general formula (!), Are applied by a spray application to appropriate plants or plant parts to be treated. The use according to the invention of the compounds of the general formula (I) or salts thereof is preferably carried out with a dosage of between 0.00005 and 3 kg / ha, more preferably between 0.0001 and 2 kg / ha, particularly preferably between 0.0005 and 1 kg / ha, more preferably between 0.001 and 0.25 kg / ha. If abscisic acid is used simultaneously with substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles of the general formula (I) in the context of the present invention, for example in the context of a common preparation or formulation, the admixing of abscisic acid is preferably carried out in one dosage between 0.0001 and 3 kg / ha, more preferably between 0.001 and 2 kg / ha, particularly preferably between 0.005 and 1 kg / ha, in particular preferably between 0.006 and 0.25 kg / ha.
Unter der Bezeichnung Resistenz bzw. Widerstandsfähigkeit gegenüber abiotischem Stress werden im Rahmen der vorliegenden Erfindung verschiedenartige Vorteile für Pflanzen verstanden. Solche vorteilhaften Eigenschaften äußern sich beispielsweise in den nachfolgend genannten verbesserten Pflanzencharakteristika: verbessertes Wurzelwachstum hinsichtlich Oberfläche und Tiefe, vermehrte Ausläuferbildung oder Bestückung, stärkere und produktivere Ausläufer und Bestockungstriebe, In the context of the present invention, the term resistance or resistance to abiotic stress is understood to mean various advantages for plants. Such advantageous properties are manifested, for example, in the following improved plant characteristics: improved root growth in terms of surface area and depth, increased tailing or stocking, stronger and more productive shoots and tillers,
Verbesserung des Sproßwachstums, erhöhte Standfestigkeit, vergrößerte Improvement of shoot growth, increased stability, increased
Sprossbasisdurchmesser, vergrößerte Blattfläche, höhere Erträge an Nähr- und Inhaltsstoffen, wie z.B. Kohlenhydrate, Fette, Öle, Proteine, Vitamine, Mineralstoffe, ätherische Öle, Farbstoffe, Fasern, bessere Faserqualität, früheres Blühen, gesteigerte Blütenanzahl, reduzierter Gehalt an toxischen Produkten wie Mycotoxine, reduzierter Gehalt an Rückständen oder unvorteilhaften Bestandteilen jeglicher Art oder bessere Verdaulichkeit, verbesserte Lagerstabilität des Erntegutes, verbesserter Toleranz gegenüber unvorteilhaften Temperaturen, verbesserter Toleranz gegenüber Dürre und Trockenheit, wie auch Sauerstoffmangel durch Wasserüberschuß, verbesserte Sprout base diameter, increased leaf area, higher yields of nutrients and ingredients, such as carbohydrates, fats, oils, proteins, vitamins, minerals, essential oils, dyes, fibers, better fiber quality, earlier flowering, increased number of flowers, reduced content of toxic products such as mycotoxins , reduced content of residues or unfavorable ingredients of any kind or better digestibility, improved storage stability of the crop, improved tolerance to unfavorable temperatures, improved tolerance to drought and Dryness, as well as lack of oxygen due to excess water, improved
Toleranz gegenüber erhöhten Salzgehalten in Böden und Wasser, gesteigerte Tolerance to increased salt levels in soils and water, increased
Toleranz gegenüber Ozonstress, verbesserte Verträglichkeit gegenüber Herbiziden und anderen Pflanzenbehandlungsmitteln, verbesserte Wasseraufnahme und Tolerance to ozone stress, improved tolerance to herbicides and other plant treatment agents, improved water absorption and
Photosyntheseleistung, vorteilhafte Pflanzeneigenschaften, wie beispielsweise Photosynthesis, beneficial plant properties, such as
Beschleunigung der Reifung, gleichmäßigere Abreife, größere Anziehungskraft für Nützlinge, verbesserte Bestäubung oder andere Vorteile, die einem Fachmann durchaus bekannt sind. Insbesondere zeigt die erfindungsgemäße Verwendung einer oder mehrerer Acceleration of ripening, more uniform ripening, greater attractiveness for beneficials, improved pollination or other benefits well known to those skilled in the art. In particular, the use according to the invention shows one or more
Verbindungen der allgemeinen Formel (I) in der Sprühapplikation auf Pflanzen und Pflanzenteilen die beschriebenen Vorteile. Kombinationen von den  Compounds of general formula (I) in the spray application to plants and parts of plants the advantages described. Combinations of the
erfindungsgemäßen substituierten 2-Amidobenzimidazolen, 2-Amidobenzoxazolen und 2 -Amidobenzothiazolen der allgemeinen Formel (I) unter anderem mit Insektiziden, Lockstoffen, Akariziden, Fungiziden, Nematiziden, Herbiziden, substituted 2-amidobenzimidazoles according to the invention, 2-amidobenzoxazoles and 2-amidobenzothiazoles of the general formula (I) inter alia with insecticides, attractants, acaricides, fungicides, nematicides, herbicides,
wachstumsregulierenden Stoffen, Safenern, die Pflanzenreife beeinflussenden Stoffen und Bakteriziden können bei der Bekämpfung von Pflanzenkrankheiten und/oder zur Erzielung einer Ertragssteigerung im Rahmen der vorliegenden Erfindung ebenfalls Anwendung finden. Die kombinierte Verwendung von erfindungsgemäßen Growth regulators, safeners, plant ripeness affecting substances and bactericides can also find application in the control of plant diseases and / or to achieve an increase in yield in the context of the present invention. The combined use of inventive
substituierten 2-Amidobenzimidazolen, 2-Amidobenzoxazolen und 2-substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-
Amidobenzothiazolen der allgemeinen Formel (I) mit gentechnisch veränderten Sorten in Bezug auf erhöhte abiotische Stresstoleranz ist darüber hinaus ebenfalls möglich. Amidobenzothiazoles of general formula (I) with genetically modified varieties with respect to increased abiotic stress tolerance is also possible.
Die weiter oben genannten verschiedenartigen Vorteile für Pflanzen lassen sich bekannterweise partiell zusammenfassen und mit allgemein gültigen Begriffen belegen. Soche Begriffe sind beispielsweise die nachfolgend aufgeführten The various advantages for plants mentioned above can, as is known, be partially summarized and substantiated by generally valid terms. Soche terms are, for example, those listed below
Bezeichnungen: phytotonischer Effekt, Widerstandsfähigkeit gegenüber Terms: phytotonic effect, resistance to
Stressfaktoren, weniger Pflanzenstress, Pflanzengesundheit, gesunde Pflanzen, Pflanzenfitness, („Plant Fitness"),„Plant Wellness",„Plant Concept",„Vigor Effect", „Stress Shield", Schutzschild,„Crop Health",„Crop Health Properties",„Crop Health Products",„Crop Health Management",„Crop Health Therapy",„Plant Health", Plant Health Properties", Plant Health Products",„Plant Health Management",„Plant Health Therapy", Grünungseffekt („Greening Effect" oder„Re-greening Effect"),„Freshness" oder andere Begriffe, die einem Fachmann durchaus bekannt sind. Im Rahmen der vorliegenden Erfindung wird unter einem guten Effekt auf die Stress Factors, Less Plant Stress, Plant Health, Healthy Plants, Plant Fitness, Plant Wellness, Plant Concept, Vigor Effect, Stress Shield, Shield, Crop Health, Crop Health Properties "Crop Health Products", "Crop Health Management", "Crop Health Therapy", "Plant Health", Plant Health Properties, "Plant Health Products", "Plant Health Management", "Plant Health Therapy", Greening Effect (" Greening effect "or" re-greening effect ")," Freshness "or other terms that are well known to a person skilled in the art. In the present invention is under a good effect on the
Widerstandsfähigkeit gegenüber abiotischem Stress nicht beschränkend · mindestens ein um im Allgemeinen 3 %, insbesondere größer als 5 % Non-limiting resistance to abiotic stress · at least one in general 3%, in particular greater than 5%
besonders bevorzugt größer als 10 % verbessertes Auflaufen, more preferably greater than 10% improved emergence,
mindestens einen im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % gesteigerten Ertrag,  at least one generally 3%, in particular greater than 5%, particularly preferably greater than 10% increased yield,
mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % verbesserte Wurzelentwicklung,  at least one root development generally improved by 3%, in particular greater than 5%, particularly preferably greater than 10%,
mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % ansteigende Sproßgröße,  at least one shoot size increasing by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % vergrößerte Blattfläche,  at least one leaf area increased by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
· mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % verbesserte Photosyntheseleistung und/oder mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % verbesserte Blütenausbildung verstanden, wobei die Effekte einzeln oder aber in beliebiger Kombination von zwei oder mehreren Effekten auftreten können. · At least one generally improved by 3%, in particular greater than 5%, more preferably greater than 10% improved photosynthesis and / or at least one by generally 3%, especially greater than 5%, particularly preferably greater than 10% improved flower formation understood, said Effects can occur individually or in any combination of two or more effects.
Weiterer Gegenstand der vorliegenden Erfindung ist eine Sprühlösung zur Behandlung von Pflanzen, enthaltend eine zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren wirksame Menge von mindestens einer A further subject of the present invention is a spray solution for the treatment of plants, comprising an amount of at least one effective for increasing the resistance of plants to abiotic stress factors
Verbindung aus der Gruppe der 2-Amidobenzimidazole, 2-Amidobenzoxazole und 2- Amidobenzothiazole der allgemeinen Formel (I). Die Sprühlösung kann andere übliche Bestandteile aufweisen, wie Lösungsmittel, Formulierhilfsstoffe, insbesondere Wasser, enthalten. Weitere Bestandteile können unter anderem agrochemische Wirkstoffe sein, welche unten noch weiter beschrieben werden.  A compound from the group of 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles of the general formula (I). The spray solution may comprise other conventional ingredients, such as solvents, formulation auxiliaries, especially water. Other ingredients may include agrochemical agents, which are further described below.
Weiterer Gegenstand der vorliegenden Erfindung ist die Verwendung von Another object of the present invention is the use of
entsprechenden Sprühlösungen zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren. Die nachfolgenden Ausführungen gelten sowohl für die erfindungsgemäße Verwendung einer oder mehrerer Verbindungen der allgemeinen Formel (I) an sich als auch für die entsprechenden Sprühlösungen. corresponding spray solutions to increase the resistance of plants to abiotic stress factors. The following explanations apply both for the inventive use of one or more compounds of general formula (I) per se and for the corresponding spray solutions.
Erfindunsgemäß wurde darüber hinaus gefunden, dass die Anwendung einer oder mehrerer Verbindungen der allgemeinen Formel (I) in Kombination mit mindestens einem Düngemittel wie weiter unten stehend definiert auf Pflanzen oder in deren Umgebung möglich ist. According to the invention, moreover, it has been found that the use of one or more compounds of general formula (I) in combination with at least one fertilizer as defined below is possible on plants or in their environment.
Düngemittel, die erfindungsgemäß zusammen mit den oben näher erläuterten Fertilizers according to the invention together with the above explained in more detail
Verbindungen der allgemeinen Formel (!) verwendet werden können, sind im Compounds of the general formula (!) Can be used are in
Allgemeinen organische und anorganische Stickstoff-haltige Verbindungen wie beispielsweise Harnstoffe, Harnstoff-Formaldehyd-Kondensationsprodukte, General organic and inorganic nitrogen-containing compounds such as, for example, ureas, urea-formaldehyde condensation products,
Aminosäuren, Ammoniumsalze und -nitrate, Kaliumsalze (bevorzugt Chloride, Sulfate, Nitrate), Phosphorsäuresalze und/oder Salze von Phosphoriger Säure (bevorzugt Kaliumsalze und Ammoniumsalze). Insbesondere zu nennen sind in diesem Amino acids, ammonium salts and nitrates, potassium salts (preferably chlorides, sulfates, nitrates), phosphoric acid salts and / or salts of phosphorous acid (preferably potassium salts and ammonium salts). To name in particular are in this
Zusammenhang die NPK-Dünger, d.h. Düngemittel, die Stickstoff, Phosphor und Kalium enthalten, Kalkammonsalpeter, d.h. Düngemittel, die noch Calcium enthalten, Ammonsulfatsalpeter (Allgemeine Formel (NH4)2S04 NH4NO3), Ammonphosphat und Ammonsulfat. Diese Düngemittel sind dem Fachmann allgemein bekannt, siehe auch beispielsweise Ullmann's Encyclopedia of Industrial Chemistry, 5. Edition, Vol. A 10, Seiten 323 bis 431 , Verlagsgesellschaft, Weinheim, 1987. Related to NPK fertilizers, ie fertilizers containing nitrogen, phosphorus and potassium, calcium ammonium nitrate, ie fertilizers which still contain calcium, ammonium sulphate nitrate (general formula (NH 4 ) 2 SO 4 NH 4 NO 3), ammonium phosphate and ammonium sulphate. These fertilizers are well known to those skilled in the art, see also, for example, Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A 10, pages 323 to 431, Verlagsgesellschaft, Weinheim, 1987.
Die Düngemittel können auch Salze aus Mikronährstoffen (bevorzugt Calcium, The fertilizers may also contain salts of micronutrients (preferably calcium,
Schwefel, Bor, Mangan, Magnesium, Eisen, Bor, Kupfer, Zink, Molybdän und Kobalt) und Phytohormonen (z. B. Vitamin B1 und Indol-(lll)essigsäure) oder Gemische davon enthalten. Erfindungsgemäß eingesetzte Düngemittel können auch weitere Salze wie Monoammoniumphosphat (MAP), Diammoniumphosphat (DAP), Kaliumsulfat, Sulfur, boron, manganese, magnesium, iron, boron, copper, zinc, molybdenum and cobalt) and phytohormones (eg, vitamin B1 and indole (III) acetic acid) or mixtures thereof. Fertilizers used according to the invention may also contain other salts such as monoammonium phosphate (MAP), diammonium phosphate (DAP), potassium sulfate,
Kaliumchlorid, Magnesiumsulfat enthalten. Geeignete Mengen für die sekundären Nährstoffe oder Spurenelemente sind Mengen von 0,5 bis 5 Gew.-%, bezogen auf das gesamte Düngemittel. Weitere mögliche Inhaltsstoffe sind Pflanzenschutzmittel, Insektizide oder Fungizide, Wachstumsregulatoren oder Gemische davon. Hierzu folgen weiter unten weitergehende Ausführungen. Die Düngemittel können beispielsweise in Form von Pulvern, Granulaten, Prills oder Kompaktaten eingesetzt werden. Die Düngemittel können jedoch auch in flüssiger Form, gelöst in einem wässrigen Medium, eingesetzt werden. In diesem Fall kann auch verdünnter wässriger Ammoniak als Stickstoffdüngemittel eingesetzt werden. Weitere mögliche Inhaltsstoffe für Düngemittel sind beispielsweise in Ullmann's Containing potassium chloride, magnesium sulfate. Suitable amounts for the secondary nutrients or trace elements are amounts of 0.5 to 5 wt .-%, based on the total fertilizer. Further possible ingredients are crop protection agents, insecticides or fungicides, growth regulators or mixtures thereof. Further explanations follow below. The fertilizers can be used, for example, in the form of powders, granules, prills or compactates. However, the fertilizers can also be used in liquid form dissolved in an aqueous medium. In this case, dilute aqueous ammonia can be used as nitrogen fertilizer. Further possible ingredients for fertilizers are, for example, in Ullmann's
Encyclopedia of Industrial Chemistry, 5. Auflage, 1987, Band A 10, Seiten 363 bis 401 , DE-A 41 28 828, DE-A 19 05 834 und DE-A 196 31 764 beschrieben. Die allgemeine Zusammensetzung der Düngemittel, bei welchen es sich im Rahmen der vorliegenden Erfindung um Einzelnährstoff- und/oder Mehrnährstoffdünger handeln kann,  Encyclopedia of Industrial Chemistry, 5th edition, 1987, Volume A 10, pages 363 to 401, DE-A 41 28 828, DE-A 19 05 834 and DE-A 196 31 764 described. The general composition of the fertilizers, which in the context of the present invention may be single-nutrient and / or complex nutrient fertilizers,
beispielsweise aus Stickstoff, Kalium oder Phosphor, kann innerhalb eines breiten Bereichs variieren. Im Allgemeinen ist ein Gehalt von 1 bis 30 Gew.-% Stickstoff (bevorzugt 5 bis 20 Gew.-%), von 1 bis 20 Gew.-% Kalium (bevorzugt 3 bis 15 Gew.- %) und ein Gehalt von 1 bis 20 Gew.-% Phosphor (bevorzugt 3 bis 10 Gew.-%) vorteilhaft. Der Gehalt von Mikroelementen ist üblicherweise im ppm-Bereich, bevorzugt im Bereich von von 1 bis 1000 ppm. For example, nitrogen, potassium or phosphorus may vary within a wide range. In general, a content of 1 to 30 wt .-% of nitrogen (preferably 5 to 20 wt .-%), from 1 to 20 wt .-% potassium (preferably 3 to 15% by weight) and a content of 1 to 20% by weight of phosphorus (preferably 3 to 10% by weight) is advantageous. The content of microelements is usually in the ppm range, preferably in the range of from 1 to 1000 ppm.
Im Rahmen der vorliegenden Erfindung können das Düngemittel sowie eine oder mehrere Verbindungen der allgemeinen Formel (I) zeitgleich verabreicht werden. Es ist jedoch auch möglich, zunächst das Düngemittel und dann eine oder mehrere In the context of the present invention, the fertilizer and one or more compounds of the general formula (I) can be administered at the same time. However, it is also possible first the fertilizer and then one or more
Verbindungen der allgemeinen Formel (I) oder zunächst eine oder mehrere Compounds of general formula (I) or first one or more
Verbindungen der allgemeinen Formel (I) und dann das Düngemittel anzuwenden. Bei nicht zeitgleicher Anwendung einer oder mehrerer Verbindungen der allgemeinen Formel (I) und des Düngemittels erfolgt im Rahmen der vorliegenden Erfindung jedoch die Anwendung in funktionellem Zusammenhang, insbesondere innerhalb eines Zeitraums von im Allgemeinen 24 Stunden, bevorzugt 18 Stunden, besonders bevorzugt 12 Stunden, speziell 6 Stunden, noch spezieller 4 Stunden, noch weiter spezieller innerhalb 2 Stunden. In ganz besonderen Ausführungsformen der  Apply compounds of general formula (I) and then the fertilizer. In the case of non-simultaneous application of one or more compounds of the general formula (I) and of the fertilizer, however, the application is carried out in a functional context, especially within a period of generally 24 hours, preferably 18 hours, more preferably 12 hours, especially 6 hours, more specifically 4 hours, even more special within 2 hours. In very particular embodiments of the
vorliegenden Erfindung erfolgt die Anwendung einer oder mehrerer present invention, the application of one or more
erfindungsgemäßer Verbindungen der Formel (I) und des Düngemittels in einem zeitlichen Rahmen von weniger als 1 Stunden, vorzugsweise weniger als 30 Minuten, besonders bevorzugt weniger als 15 Minuten. inventive compounds of formula (I) and the fertilizer in a time frame of less than 1 hour, preferably less than 30 minutes, more preferably less than 15 minutes.
Bevorzugt ist die Verwendung von Verbindungen der allgemeinen Formel (I) auf Pflanzen aus der Gruppe der Nutzpflanzen, Zierpflanzen, Rasenarten, allgemein genutzte Bäume, die in öffentlichen und privaten Bereichen als Zierpflanzen Preference is given to the use of compounds of the general formula (I) on plants from the group of crops, ornamental plants, lawn species, in general used trees as ornamental plants in public and private areas
Verwendungen finden, und Forstbestand. Der Forstbestand umfasst Bäume für die Herstellung von Holz, Zellstoff, Papier und Produkten die aus Teilen der Bäume hergestellt werden. Der Begriff Nutzpflanzen, wie hier verwendet, bezeichnet Find uses, and forest stands. The forest stock includes trees for the production of wood, pulp, paper and products made from parts of the trees. The term crops as used herein refers to
Kulturpflanzen, die als Pflanzen für die Gewinnung von Nahrungsmitteln, Futtermitteln, Treibstoffe oder für technische Zwecke eingesetzt werden. Crop plants used as plants for the production of food, feed, fuel or for technical purposes.
Zu den Nutzpflanzen zählen z. B. folgende Pflanzenarten: Triticale, Durum Among the useful plants include z. For example, the following plant species: Triticale, Durum
(Hartweizen), Turf, Reben, Getreide, beispielsweise Weizen, Gerste, Roggen, Hafer, Reis, Mais und Hirse; Rüben, beispielsweise Zuckerrüben und Futterrüben; Früchte, beispielsweise Kernobst, Steinobst und Beerenobst, beispielsweise Äpfel, Birnen, Pflaumen, Pfirsiche, Mandeln, Kirschen und Beeren, z. B. Erdbeeren, Himbeeren, Brombeeren; Hülsenfrüchte, beispielsweise Bohnen, Linsen, Erbsen und Sojabohnen; Ölkulturen, beispielsweise Raps, Senf, Mohn, Oliven, Sonnenblumen, Kokos, (Durum wheat), turf, vines, cereals, such as wheat, barley, rye, oats, rice, corn and millet; Beets, for example sugar beets and fodder beets; Fruits, such as pome fruit, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries and berries, eg. Strawberries, raspberries, blackberries; Legumes, such as beans, lentils, peas and soybeans; Oil crops, such as oilseed rape, mustard, poppy, olives, sunflowers, coconut,
Castorölpflanzen, Kakaobohnen und Erdnüsse; Gurkengewächse, beispielsweise Kürbis, Gurken und Melonen; Fasergewächse, beispielsweise Baumwolle, Flachs, Hanf und Jute; Citrusfrüchte, beispielsweise Orangen, Zitronen, Pampelmusen und Mandarinen; Gemüsesorten, beispielsweise Spinat, (Kopf)-Salat, Spargel, Kohlarten, Möhren, Zwiebeln, Tomaten, Kartoffeln und Paprika; Lorbeergewächse, beispielsweise Avocado, Cinnamomum, Kampfer, oder ebenso Pflanzen wie Tabak, Nüsse, Kaffee, Aubergine, Zuckerrohr, Tee, Pfeffer, Weinreben, Hopfen, Bananen, Castor oil plants, cocoa beans and peanuts; Cucurbits, for example squash, cucumbers and melons; Fiber plants, for example cotton, flax, hemp and jute; Citrus fruits, such as oranges, lemons, grapefruit and mandarins; Vegetables such as spinach, (head) salad, asparagus, cabbages, carrots, onions, tomatoes, potatoes and peppers; Laurel family, such as avocado, cinnamomum, camphor, or plants such as tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, vines, hops, bananas,
Naturkautschukgewächse sowie Zierpflanzen, beispielsweise Blumen, Sträucher, Laubbäume und Nadelbäume wie Koniferen. Diese Aufzählung stellt keine Limitierung dar. Natural rubber plants and ornamental plants, such as flowers, shrubs, deciduous trees and conifers such as conifers. This list is not a limitation.
Als besonders geeignete Zielkulturen für die Anwendung des erfindungsgemäßen Verfahrens sind folgende Pflanzen anzusehen: Hafer, Roggen, Triticale, Durum, Baumwolle, Aubergine, Turf, Kernobst, Steinobst, Beerenobst, Mais, Weizen, Gerste, Gurke, Tabak, Reben, Reis, Getreide, Birne, Pfeffer, Bohnen, Sojabohnen, Raps, Tomate, Paprika, Melonen, Kohl, Kartoffel und Apfel. Particularly suitable target crops for the application of the method according to the invention are the following plants: oats, rye, triticale, durum, cotton, aubergine, turf, pome fruit, stone fruit, berry fruit, corn, wheat, barley, cucumber, tobacco, vines, rice, cereals , Pear, pepper, beans, soybeans, rape, tomato, paprika, melons, cabbage, potato and apple.
Als Bäume, die entsprechend dem erfindungsgemäßen Verfahren verbessert werden können, seien beispielhaft genannt: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., PSatanus sp., Tilia sp., Acer sp., Tsuga sp., Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp.. Examples of trees which can be improved according to the process of the invention are: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., PSatanus sp., Tilia sp., Acer sp., Tsuga sp., Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp ., Populus sp ..
Als bevorzugte Bäume, die entsprechend dem erfindungsgemäßen Verfahren verbessert werden können, können genannt werden: Aus der Baumart Aesculus: A. hippocastanum, A. pariflora, A. carnea; aus der Baumart Platanus: P. aceriflora, P. occidentalis, P. racemosa; aus der Baumart Picea: P. abies; aus der Baumart Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P. As preferred trees, which can be improved according to the method of the invention, may be mentioned: From the tree species Aesculus: A. hippocastanum, A. pariflora, A. carnea; from the tree species Platanus: P. aceriflora, P. occidentalis, P. racemosa; from the tree species Picea: P. abies; from the tree Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P.
albicaulis, P. resinosa, P. palustris, P. taeda, P. flexilis, P. jeffregi, P. baksiana, P. strobes; aus der Baumart Eucalyptus: E. grandis, E. globulus, E. camadentis, E. albicaulis, P. resinosa, P. palustris, P. taeda, P. flexilis, P. jeffregi, P. baksiana, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis, E.
nitens, E. obliqua, E. regnans, E. pilularus. nitens, E. obliqua, E. regnans, E. pilularus.
Als besonders bevorzugte Bäume, die entsprechend dem erfindungsgemäßen As particularly preferred trees, according to the invention
Verfahren verbessert werden können, können genannt werden: Aus der Baumart Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. strobes; aus der Baumart Eucalyptus: E. grandis, E. globulus und E. camadentis. Methods can be improved can be mentioned: From the tree species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus and E. camadentis.
Als besonders bevorzugte Bäume, die entsprechend dem erfindungsgemäßen As particularly preferred trees, according to the invention
Verfahren verbessert werden können, können genannt werden: Rosskastanie, Procedures can be improved: horse chestnut,
Platanengewächs, Linde und Ahornbaum. Sycamore plant, linden and maple tree.
Die vorliegende Erfindung kann auch an beliebigen Rasenarten („turfgrasses") durchgeführt werden, einschließlich„cool season turfgrasses" und„warm season turfgrasses". Beispiele für Rasenarten für die kalte Jahreszeit sind Blaugräser („blue grasses"; Poa spp.), wie„Kentucky bluegrass" (Poa pratensis L),„rough bluegrass" (Poa trivialis L),„Canada bluegrass" (Poa compressa L),„annual bluegrass" (Poa annua L),„upland bluegrass" (Poa glaucantha Gaudin),„wood bluegrass" (Poa nemoralis L.) und„bulbous bluegrass" (Poa bulbosa L); Straussgräser („Bentgrass", Agrostis spp.), wie„creeping bentgrass" (Agrostis palustris Huds.),„colonial bentgrass" (Agrostis tenuis Sibth.),„velvet bentgrass" (Agrostis canina L),„South German Mixed Bentgrass" (Agrostis spp. einschließlich Agrostis tenius Sibth., Agrostis canina L, und Agrostis palustris Huds.), und„redtop" (Agrostis alba L); Schwingel („Fescues", Festucu spp.), wie„red fescue" (Festuca rubra L. spp. rubra), „creeping fescue" (Festuca rubra L),„chewings fescue" (Festuca rubra commutata Gaud.),„sheep fescue" (Festuca ovina L),„hard fescue" (Festuca longifolia Thuill.), „hair fescue" (Festucu capiilata Lam.),„tall fescue" (Festuca arundinacea Schreb.) und „meadow fescue" (Festuca elanor L); The present invention may also be practiced on any turfgrasses, including "cool season turfgrasses" and "warm season turfgrasses." Examples of cold season turf species are blue grasses (Poa spp.), Such as "Kentucky bluegrass" (Poa pratensis L), "rough bluegrass" (Poa trivialis L), "Canada bluegrass" (Poa compressa L), "annual bluegrass" (Poa annua L), "upland bluegrass" (Poa glaucantha Gaudin), "Wood bluegrass" (Poa nemoralis L.) and "bulbous bluegrass" (Poa bulbosa L); ostrich grasses ("Bentgrass", Agrostis spp.), Such as "creeping bentgrass" (Agrostis palustris Huds.), "Colonial bentgrass" (Agrostis Tenuis Sibth.), "velvet bentgrass" (Agrostis canina L), "South German Mixed Bentgrass" (Agrostis spp., including Agrostis tenius Sibth., Agrostis canina L, and Agrostis palustris Huds.), and "redtop" (Agrostis alba L ); Fescue ("Fescues", Festucu spp.), Such as "red fescue" (Festuca rubra L. spp. Rubra), "creeping fescue" (Festuca rubra L), "chewings fescue" (Festuca rubra commutata Gaud.), "Sheep fescue "(Festuca ovina L)," hard fescue "(Festuca longifolia Thuill.)," hair fescue "(Festucu capiilata Lam.)," tall fescue "(Festuca arundinacea Schreb.) and" meadow fescue "(Festuca elanor L) ;
Lolch („ryegrasses", Lolium spp.), wie„annual ryegrass" (Lolium multiflorum Lam.), „perennial ryegrass" (Lolium perenne L.) und„italian ryegrass" (Lolium multiflorum Lam.); und Weizengräser ("wheatgrasses", Agropyron spp..), wie "fairway wheatgrass" (Agropyron cristatum (L.) Gaertn.),„crested wheatgrass" (Agropyron desertorum (Fisch.) Schult.) und "western wheatgrass" (Agropyron smithii Rydb.). Beispiele für weitere "cool season turfgrasses" sind "beachgrass" (Ammophila breviligulata Fern.), "smooth bromegrass" (Bromus inermis Leyss.), Schilf ("cattails") wie "Timothy" (Phleum pratense L.), "sand cattail" (Phleum subulatum L.), Lolium ("ryegrasses", Lolium spp.), Such as "annual ryegrass" (Lolium multiflorum Lam.), "Perennial ryegrass" (Lolium perenne L.) and "Italian ryegrass" (Lolium multiflorum Lam.); and wheat grasses ("wheatgrasses", Agropyron spp.), such as "fairway wheatgrass" (Agropyron cristatum (L.) Gaertn.), "crested wheatgrass" (Agropyron desertorum (fish.) Schult.) and "western wheatgrass" (Agropyron smithii Rydb.) Examples of other "cool season turfgrasses" are "beachgrass" (Ammophila breviligulata Fern.), "smooth bromegrass" (Bromus inermis leyss.), reeds ("cattails") such as "Timothy" (Phleum pratense L. ), "sand cattail" (Phleum subulatum L.),
"orchardgrass" (Dactylis glomerata L.), "weeping alkaligrass" (Puccinellia distans (L.) Pari.) und "crested dog's-tail" (Cynosurus cristatus L.). "orchardgrass" (Dactylis glomerata L.), "weeping alkaligrass" (Puccinellia distans (L.) Pari.) and "crested dog's-tail" (Cynosurus cristatus L.).
Beispiele für "warm season turfgrasses" sind„Bermudagrass" (Cynodon spp. L. C. Rieh), "zoysiagrass" (Zoysia spp. Willd.),„St. Augustine grass" (Stenotaphrum secundatum Walt Kuntze),„centipedegrass" (Eremochloa ophiuroides Munro Hack.), „carpetgrass" (Axonopus affinis Chase),„Bahia grass" (Paspalum notatum Flügge), „Kikuyugrass" (Pennisetum clandestinum Höchst, ex Chiov.),„buffalo grass" (Buchloe daetyloids (Nutt.) Engelm.), "Blue gramma" (Bouteloua gracilis (H.B.K.) Lag. ex Griffiths),„seashore paspalum" (Paspalum vaginatum Swartz) und„sideoats grama" (Bouteloua curtipendula (Michx. Torr.). "Cool season turfgrasses" sind für die erfindungsgemäße Verwendung im Allgemeinen bevorzugt. Besonders bevorzugt sind Blaugras, Straussgras und„redtop", Schwingel und Lolch. Straussgras ist Examples of "warm season turfgrasses" are "Bermudagrass" (Cynodon spp., LC Rieh), "zoysiagrass" (Zoysia spp. Willd.), "St. Augustine grass" (Stenotaphrum secundatum Walt Kuntze), "centipedegrass" (Eremochloa ophiuroides Munro Hack.), "Carpetgrass" (Axonopus affinis chase), "Bahia grass" (Paspalum notatum flügge), "Kikuyugrass" (Pennisetum clandestinum Höchst, ex Chiov.), "Buffalo grass" (Buchloe daetyloids (Nutt.) Engelm.) , "Blue gramma" (Bouteloua gracilis (HBK) lag. Ex Griffiths), "seashore paspalum" (Paspalum vaginatum Swartz) and "sideoats grama" (Bouteloua curtipendula (Michx. Torr.). "Cool season turfgrasses" are for the present invention Use is generally preferred Bleach grass, ostrich grass and "redtop", fescue and lolk are particularly preferred
insbesondere bevorzugt. especially preferred.
Besonders bevorzugt werden mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften ("Traits"), die sowohl durch konventionelle Züchtung, durch Mutagenese oder mit Hilfe rekombinanter DNA-Techniken, gezüchtet worden sind. Kulturpflanzen können demnach Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Das erfindungsgemäße Behandlungsverfahren kann somit auch für die Behandlung von genetisch modifizierten Organismen (GMOs), z. B. Pflanzen oder Samen, verwendet werden. Genetisch modifizierte Pflanzen (oder transgene Pflanzen) sind Pflanzen, bei denen ein heterologes Gen stabil in das Genom integriert worden ist. Der Begriff "heterologes Gen" bedeutet im wesentlichen ein Gen, das außerhalb der Pflanze bereitgestellt oder assembliert wird und das bei Einführung in das Particularly preferred are the compounds of general formula (I) according to the invention plants of each commercial or in use treated plant varieties. Plant varieties are understood to be plants with new traits which have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques. Crop plants can therefore be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties protectable or non-protectable plant varieties. The treatment method according to the invention can thus also for the treatment of genetically modified organisms (GMOs), z. As plants or seeds are used. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome. The term "heterologous gene" essentially means a gene that is provided or assembled outside the plant and that when introduced into the plant
Zellkerngenom, das Chloroplastengenom oder das Hypochondriengenom der transformierten Pflanze dadurch neue oder verbesserte agronomische oder sonstige Eigenschaften verleiht, dass es ein interessierendes Protein oder Polypeptid exprimiert oder dasses ein anderes Gen, das in der Pflanze vorliegt bzw. andere Gene, die in der Pflanze vorliegen, herunterreguliert oder abschaltet (zum Beispiel mittels Antisense- Technologie, Co-suppressionstechnologie oder RNAi-Technologie [RNA Interference]). Ein heterologes Gen, das im Genom vorliegt, wird ebenfalls als Transgen bezeichnet. Ein Transgen, das durch sein spezifisches Vorliegen im Pflanzengenom definiert ist, wird als Transformations- bzw. transgenes Event bezeichnet.  Cell nucleus genome, the chloroplast genome or the hypochondrial genome of the transformed plant by conferring new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by having another gene present in the plant or other genes present in the plant; downregulated or switched off (for example by means of antisense technology, co-suppression technology or RNAi technology [RNA Interference]). A heterologous gene present in the genome is also referred to as a transgene. A transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.
Zu Pflanzen und Pflanzensorten, die vorzugsweise mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden, zählen alle Pflanzen, die über Erbgut verfügen, das diesen Pflanzen besonders vorteilhafte, nützliche Merkmale verleiht (egal, ob dies durch Züchtung und/oder Biotechnologie erzielt wurde). Plants and plant varieties which are preferably treated with the compounds of the general formula (I) according to the invention include all plants which have genetic material which gives these plants particularly advantageous, useful features (regardless of whether this is achieved by breeding and / or biotechnology has been).
Pflanzen und Pflanzensorten, die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind solche Pflanzen, die gegen einen oder mehrere abiotische Streßfaktoren resistent sind. Zu den abiotischen Plants and plant varieties which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are resistant to one or more abiotic stress factors. To the abiotic
Streßbedingungen können zum Beispiel Hitze, Dürre, Kälte- und Trockenstress,, osmotischer Streß, Staunässe, erhöhter BodensalzgehaSt, erhöhtes Ausgesetztsein an Mineralien, Ozonbedingungen, Starklichtbedingungen, beschränkte Verfügbarkeit vonStress conditions can include, for example, heat, drought, cold and dry stress, osmotic stress, waterlogging, increased soil salt content, increased exposure to minerals, ozone conditions, high light conditions, limited availability of
Stickstoffnährstoffen, beschränkte Verfügbarkeit von Phosphornährstoffen oder Vermeidung von Schatten zählen. Nitrogen nutrients, limited availability of phosphorus nutrients or avoiding shadows.
Pflanzen und Pflanzensorten, die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind solche Pflanzen, die durch erhöhte Ertragseigenschaften gekennzeichnet sind. Ein erhöhter Ertrag kann bei diesen Pflanzen z. B. auf verbesserter Pflanzenphysiologie, verbessertem Plants and plant varieties which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are characterized by increased yield properties. An increased yield can in these plants z. B. on improved plant physiology, improved
Pflanzenwuchs und verbesserter Pflanzenentwicklung, wie Plant growth and improved plant development, such as
Wasserverwertungseffizienz, Wasserhalteeffizienz, verbesserter Stickstoffverwertung, erhöhter Kohlenstoffassimilation, verbesserter Photosynthese, verstärkter Keimkraft und beschleunigter Abreife beruhen. Der Ertrag kann weiterhin durch eine verbesserte Pflanzenarchitektur (unter Streß- und nicht-Streß-Bedingungen) beeinflußt werden, darunter frühe Blüte, Kontrolle der Blüte für die Produktion von Hybridsaatgut,  Water utilization efficiency, water retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, increased germination power and accelerated Abreife based. The yield may be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for the production of hybrid seed,
Keimpflanzenwüchsigkeit, Pflanzengröße, Internodienzahl und -abstand, Seedling vigor, plant size, internode count and distance,
Wurzelwachstum, Samengröße, Fruchtgröße, Schotengröße, Schoten- oder Root growth, seed size, fruit size, pod size, pods or
Ährenzahl, Anzahl der Samen pro Schote oder Ähre, Samenmasse, verstärkte Ear number, number of seeds per pod or ear, seed mass, strengthened
Samenfüllung, verringerter Samenausfall, verringertes Schotenplatzen sowie Seed filling, reduced seed failure, reduced pod popping as well
Standfestigkeit. Zu weiteren Ertragsmerkmalen zählen Samenzusammensetzung wie Kohlenhydratgehalt, Proteingehait, Ölgehalt und Ölzusammensetzung, Nährwert, Verringerung der nährwidrigen Verbindungen, verbesserte Verarbeitbarkeit und verbesserte Lagerfähigkeit. Pflanzen, die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Hybridpflanzen, die bereits die Stability. Other yield-related traits include seed composition such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction in nontoxic compounds, improved processability, and improved shelf life. Plants which can also be treated with the compounds of the general formula (I) according to the invention are hybrid plants which have already been used
Eigenschaften der Heterosis bzw. des Hybrideffekts exprimieren, was im allgemeinen zu höherem Ertrag, höherer Wüchsigkeit, besserer Gesundheit und besserer Characteristics of heterosis or hybrid effect, which generally results in higher yield, higher vigor, better health and better
Resistenz gegen biotische und abiotische Streßfaktoren führt. Solche Pflanzen werden typischerweise dadurch erzeugt, dass man eine ingezüchtete pollensterile Elternlinie (den weiblichen Kreuzungspartner) mit einer anderen ingezüchteten pollenfertilen Elternlinie (dem männlichen Kreuzungspartner) kreuzt. Das Hybridsaatgut wird typischerweise von den pollensterilen Pflanzen geerntet und an Vermehrer verkauft. Pollensterile Pflanzen können manchmal (z. B. beim Mais) durch Entfahnen (d. h. mechanischem Entfernen der männlichen Geschlechtsorgane bzw. der männlichen Blüten), produziert werden; es ist jedoch üblicher, dass die Pollensterilität auf genetischen Determinanten im Pflanzengenom beruht. In diesem Fall, insbesondere dann, wenn es sich bei dem gewünschten Produkt, da man von den Hybridpflanzen ernten will, um die Samen handelt, ist es üblicherweise günstig, sicherzustellen, dass die Pollenfertilität in Hybridpflanzen, die die für die Pollensterilität verantwortlichen genetischen Determinanten enthalten, völlig restoriert wird. Dies kann erreicht werden, indem sichergestellt wird, dass die männlichen Kreuzungspartner entsprechende Fertilitätsrestorergene besitzen, die in der Lage sind, die Pollenfertilität in Resistance to biotic and abiotic stress factors leads. Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner). The hybrid seed is typically harvested from the male sterile plants and sold to propagators. Pollen sterile plants can sometimes (for example in the case of corn) by Entfahnen (ie mechanical removal of male genitalia or male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome. In this case, especially when the desired product, as one wants to harvest from the hybrid plants, is the seeds, it is usually beneficial to ensure that the pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility , completely restored. This can be accomplished by ensuring that the male crossbred partners possess appropriate fertility restorer genes capable of controlling pollen fertility in humans
Hybridpflanzen, die die genetischen Determinanten, die für die Pollensterilität verantwortlich sind, enthalten, zu restorieren. Genetische Determinanten für Hybrid plants that contain the genetic determinants responsible for male sterility. Genetic determinants for
Pollensterilität können im Cytoplasma lokalisiert sein. Beispiele für cytoplasmatische Pollensterilität (CMS) wurden zum Beispiel für Brassica-Arten beschrieben (WO 92/005251 , WO 95/009910, WO 98/27806, WO 05/002324, WO 06/021972 und US 6,229,072). Genetische Determinanten für Pollensterilität können jedoch auch imPollen sterility may be localized in the cytoplasm. Examples of cytoplasmic male sterility (CMS) have been described, for example, for Brassica species (WO 92/005251, WO 95/009910, WO 98/27806, WO 05/002324, WO 06/021972 and US 6,229,072). However, genetic determinants of pollen sterility can also be found in the
Zellkerngenom lokalisiert sein. Pollensterile Pflanzen können auch mit Methoden der pflanzlichen Biotechnologie, wie Gentechnik, erhalten werden. Ein besonders günstiges Mittel zur Erzeugung von pollensterilen Pflanzen ist in WO 89/10396 beschrieben, wobei zum Beispiel eine Ribonuklease wie eine Barnase selektiv in den Tapetumzellen in den Staubblättern exprimiert wird. Die Fertilität kann dann durch Expression eines Ribonukleasehemmers wie Barstar in den Tapetumzellen restoriert werden (z. B. WO 91/002069). Be located nuclear genome. Pollen sterile plants can also be obtained using plant biotechnology methods such as genetic engineering. A particularly convenient means of producing male-sterile plants is described in WO 89/10396, wherein, for example, a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens. The fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells (eg WO 91/002069).
Pflanzen oder Pflanzensorten (die mit Methoden der Pflanzenbiotechnologie, wie der Gentechnik, erhalten werden), die ebenfalls mit den erfindungsgemäßen Plants or plant varieties (which are obtained by plant biotechnology methods, such as genetic engineering), which also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Compounds of general formula (I) can be treated are
herbizidtolerante Pflanzen, d. h. Pflanzen, die gegenüber einem oder mehreren vorgegebenen Herbiziden tolerant gemacht worden sind. Solche Pflanzen können entweder durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Herbizidtoleranz verleiht, erhalten werden. herbicide-tolerant plants, d. H. Plants tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation conferring such herbicide tolerance.
Herbizidtolerante Pflanzen sind zum Beispiel glyphosatetolerante Pflanzen, d. h. Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H.
Pflanzen, die gegenüber dem Herbizid Glyphosate oder dessen Salzen tolerant gemacht worden sind. So können zum Beispiel glyphosatetolerante Pflanzen durch Transformation der Pflanze mit einem Gen, das für das Enzym 5-Enolpyruvylshikimat- 3-phosphatsynthase (EPSPS) kodiert, erhalten werden. Beispiele für solche EPSPS- Gene sind das AroA-Gen (Mutante CT7) des Bakterium Salmonella typhimurium (Comai et al., Science (1983), 221 , 370-371 ), das CP4-Gen des Bakteriums Plants tolerant to the herbicide glyphosate or its salts. For example, glyphosate-tolerant plants can Transformation of the plant with a gene encoding the enzyme 5-enolpyruvylshikimat 3-phosphate synthase (EPSPS) can be obtained. Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., Science (1983), 221, 370-371), the CP4 gene of the bacterium
Agrobacterium sp. (Barry et al., Curr. Topics Plant Physiol. (1992), 7, 139-145), die Gene, die für eine EPSPS aus der Petunie (Shah et al., Science (1986), 233, 478- 481 ), für eine EPSPS aus der Tomate (Gasser et al., J. Biol. Chem. (1988), 263, 4280- 4289) oder für eine EPSPS aus Eleusine (WO 01/66704) kodieren. Es kann sich auch um eine mutierte EPSPS handeln, wie sie zum Beispiel in EP-A 0837944, WO Agrobacterium sp. (Barry et al., Curr Topics Plant Physiol. (1992), 7, 139-145), the genes responsible for petunia EPSPS (Shah et al., Science (1986), 233, 478-481). , for a EPSPS from the tomato (Gasser et al., J. Biol. Chem. (1988), 263, 4280- 4289) or for an EPSPS from Eleusine (WO 01/66704) encode. It may also be a mutated EPSPS, as described for example in EP-A 0837944, WO
00/066746, WO 00/066747 oder WO 02/026995 beschrieben ist. Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, dass man ein Gen exprimiert, das für ein Glyphosate-Oxidoreduktase-Enzym, wie es in US 5,776,760 und US 5,463,175 beschrieben ist, kodiert. Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, dass man ein Gen exprimiert, das für ein Glyphosate-acetyltransferase- Enzym, wie es in z. B. WO 02/036782, WO 03/092360, WO 05/012515 und WO 07/024782 beschrieben ist, kodiert. Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, dass man Pflanzen, die natürlich vorkommende Mutationen der oben erwähnten Gene, wie sie zum Beispiel in WO 01/024615 oder WO 00/066746, WO 00/066747 or WO 02/026995. Glyphosate-tolerant plants can also be obtained by expressing a gene coding for a glyphosate oxidoreductase enzyme as described in US 5,776,760 and US 5,463,175. Glyphosate-tolerant plants may also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described in, e.g. WO 02/036782, WO 03/092360, WO 05/012515 and WO 07/024782. Glyphosate-tolerant plants can also be obtained by culturing plants containing the naturally occurring mutations of the above-mentioned genes, as described, for example, in WO 01/024615 or WO
03/013226 beschrieben sind, enthalten, selektiert. 03/013226 are described, contained, selected.
Sonstige herbizidresistente Pflanzen sind zum Beispiel Pflanzen, die gegenüber Herbiziden, die das Enzym Glutaminsynthase hemmen, wie Bialaphos, Phosphinotricin oder Glufosinate, tolerant gemacht worden sind. Solche Pflanzen können dadurch erhalten werden, dass man ein Enzym exprimiert, das das Herbizid oder eine Mutante des Enzyms Glutaminsynthase, das gegenüber Hemmung resistent ist, entgiftet. Solch ein wirksames entgiftendes Enzym ist zum Beispiel ein Enzym, das für ein Other herbicide-resistant plants are, for example, plants which have been tolerated to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate. Such plants can be obtained by expressing an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition. Such an effective detoxifying enzyme is, for example, an enzyme suitable for
Phosphinotricin-acetyltransferase kodiert (wie zum Beispiel das bar- oder pat-Protein aus Streptomyces-Arten). Pflanzen, die eine exogene Phosphinotricin- acetyltransferase exprimieren, sind zum Beispiel in US 5,561 ,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 und US 7,1 12,665 beschrieben. Phosphinotricin acetyltransferase encoded (such as the bar or pat protein from Streptomyces species). Plants expressing an exogenous phosphinotricin acetyltransferase are described, for example, in US 5,561,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 and US 7,112,665.
Weitere herbizidtolerante Pflanzen sind auch Pflanzen, die gegenüber den Herbiziden, die das Enzym Hydroxyphenylpyruvatdioxygenase (HPPD) hemmen, tolerant gemacht worden sind. Bei den Hydroxyphenylpyruvatdioxygenasen handelt es sich um Enzyme, die die Reaktion, in der para-Hydroxyphenylpyruvat (HPP) zu Homogentisat umgesetzt wird, katalysieren. Pflanzen, die gegenüber HPPD-Hemmern tolerant sind, können mit einem Gen, das für ein natürlich vorkommendes resistentes HPPD-Enzym kodiert, oder einem Gen, das für ein mutiertes HPPD-Enzym gemäß WO 96/038567, WOFurther herbicide-tolerant plants are also plants which tolerate the herbicides which inhibit the enzyme hydroxyphenylpyruvate dioxygenase (HPPD) have been. The hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate. Plants tolerant to HPPD inhibitors may be treated with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutant HPPD enzyme according to WO 96/038567, WO
99/024585 und WO 99/024586 kodiert, transformiert werden. Eine Toleranz gegenüber HPPD-Hemmern kann auch dadurch erzielt werden, dass man Pflanzen mit Genen transformiert, die für gewisse Enzyme kodieren, die die Bildung von Homogentisat trotz Hemmung des nativen HPPD-Enzyms durch den HPPD-Hemmer ermöglichen. Solche Pflanzen und Gene sind in WO 99/034008 und WO 2002/36787 beschrieben. Die Toleranz von Pflanzen gegenüber HPPD-Hemmern kann auch dadurch verbessert werden, dass man Pflanzen zusätzlich zu einem Gen, das für ein HPPD-tolerantes Enzym kodiert, mit einem Gen transformiert, das für ein Prephenatdehydrogenase- Enzym kodiert, wie dies in WO 2004/024928 beschrieben ist. 99/024585 and WO 99/024586. Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants and genes are described in WO 99/034008 and WO 2002/36787. The tolerance of plants to HPPD inhibitors can also be improved by transforming plants, in addition to a gene which codes for an HPPD-tolerant enzyme, with a gene which codes for a prephenate dehydrogenase enzyme, as described in WO 2004 / 024928 is described.
Weitere herbizidresistente Pflanzen sind Pflanzen, die gegenüber Acetolactatsynthase (ALS)-Hemmern tolerant gemacht worden sind. Zu bekannten ALS-Hemmern zählen zum Beispiel Sulfonylharnstoff, Imidazolinon, Triazolopyrimidine, Other herbicide-resistant plants are plants that have been tolerated to acetolactate synthase (ALS) inhibitors. Examples of known ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines,
Pyrimidinyloxy(thio)benzoate und/oder Sulfonylaminocarbonyltriazolinon-Herbizide. Es ist bekannt, dass verschiedene Mutationen im Enzym ALS (auch als Pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides. It is known that various mutations in the enzyme ALS (also known as
Acetohydroxysäure-Synthase, AHAS, bekannt) eine Toleranz gegenüber  Acetohydroxy acid synthase, AHAS, known) a tolerance to
unterschiedlichen Herbiziden bzw. Gruppen von Herbiziden verleihen, wie dies zum Beispiel bei Tranel und Wright, Weed Science (2002), 50, 700-712, jedoch auch in US 5,605,011 , US 5,378,824, US 5,141 ,870 und US 5,013,659, beschrieben ist. Die Herstellung von sulfonylharnstofftoleranten Pflanzen und imidazolinontoleranten Pflanzen ist in US 5,605,01 1 ; US 5,013,659; US 5,141 ,870; US 5,767,361 ; US different herbicides or groups of herbicides, as described for example in Tranel and Wright, Weed Science (2002), 50, 700-712, but also in US 5,605,011, US 5,378,824, US 5,141,870 and US 5,013,659. The preparation of sulfonylurea tolerant plants and imidazolinone tolerant plants is described in US 5,605,011 1; US 5,013,659; US 5,141,870; US 5,767,361; US
5,731 ,180; US 5,304,732; US 4,761 ,373; US 5,331 ,107; US 5,928,937; und US 5,731,180; US 5,304,732; US 4,761,373; US 5,331, 107; US 5,928,937; and US
5,378,824; sowie in der internationalen Veröffentlichung WO 96/033270 beschrieben. Weitere imidazolinontolerante Pflanzen sind auch in z. B. WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 5,378,824; and in international publication WO 96/033270. Other imidazolinontolerante plants are also in z. WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO
2006/015376, WO 2006/024351 und WO 2006/060634 beschrieben. Weitere 2006/015376, WO 2006/024351 and WO 2006/060634. Further
Sulfonylharnstoff- und imidazolinontolerante Pflanzen sind auch in z.B. WO Sulfonylurea and imidazolinone tolerant plants are also useful in e.g. WHERE
2007/024782 beschrieben. Weitere Pflanzen, die gegenüber ALS-Inhibitoren, insbesondere gegenüber 2007/024782 described. Other plants that are resistant to ALS inhibitors, especially against
Imidazolinonen, Sulfonylharnstoffen und/oder Sulfamoylcarbonyltriazolinonen tolerant sind, können durch induzierte Mutagenese, Selektion in Zellkulturen in Gegenwart des Herbizids oder durch Mutationszüchtung erhalten werden, wie dies zum Beispiel für die Sojabohne in US 5,084,082, für Reis in WO 97/41218, für die Zuckerrübe in US 5,773,702 und WO 99/057965, für Salat in US 5,198,599 oder für die Sonnenblume in WO 2001/065922 beschrieben ist. Imidazolinones, sulfonylureas and / or sulfamoylcarbonyltriazolinones, can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutagenesis, as for example for the soybean in US 5,084,082, for rice in WO 97/41218, for the sugar beet in US 5,773,702 and WO 99/057965, for salad in US 5,198,599 or for the sunflower in WO 2001/065922.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Compounds of general formula (I) can be treated are
insektenresistente transgene Pflanzen, d.h. Pflanzen, die gegen Befall mit gewissen Zielinsekten resistent gemacht wurden. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Insektenresistenz verleiht, erhalten werden. insect-resistant transgenic plants, i. Plants that have been made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance.
Der Begriff "insektenresistente transgene Pflanze" umfaßt im vorliegenden The term "insect-resistant transgenic plant" as used herein
Zusammenhang jegliche Pflanze, die mindestens ein Transgen enthält, das eine Kodiersequenz umfaßt, die für folgendes kodiert: Relates to any plant containing at least one transgene comprising a coding sequence coding for:
1 ) ein Insektizides Kristallprotein aus Bacillus thuringiensis oder einen Insektiziden Teil davon, wie die Insektiziden Kristallproteine, die von Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, zusammengestellt wurden, von Crickmore et al. (2005) in der Bacillus thuringiensis-Toxinnomenklatur aktualisiert (online bei: 1) an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof, such as the insecticidal crystal proteins collected by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, by Crickmore et al. (2005) in the Bacillus thuringiensis toxin nomenclature (online at:
http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt ), oder Insektizide Teile davon, z.B. Proteine der Cry-Proteinklassen CrylAb, CrylAc, Cryl F, Cry2Ab, Cry3Ae oder Cry3Bb oder Insektizide Teile davon; oder 2) ein Kristallprotein aus Bacillus thuringiensis oder einen Teil davon, der inhttp://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt), or insecticidal parts thereof, e.g. Proteins of Cry protein classes CrylAb, CrylAc, Cryl F, Cry2Ab, Cry3Ae or Cry3Bb or insecticidal parts thereof; or 2) a crystal protein from Bacillus thuringiensis or a part thereof which is present in
Gegenwart eines zweiten, anderen Kristallproteins als Bacillus thuringiensis oder eines Teils davon Insektizid wirkt, wie das binäre Toxin, das aus den Kristallproteinen Cy34 und Cy35 besteht (Moellenbeck et al., Nat. Biotechnol. (2001 ), 19, 668-72; Schnepf et al., Applied Environm. Microb. (2006), 71 , 1765-1774); oder 3) ein Insektizides Hybridprotein, das Teile von zwei unterschiedlichen Insektiziden Kristallproteinen aus Bacillus thuringiensis umfaßt, wie zum Beispiel ein Hybrid aus den Proteinen von 1 ) oben oder ein Hybrid aus den Proteinen von 2) oben, z. B. das Protein Cry1A.105, das von dem Mais-Event MON98034 produziert wird (WO Presence of a second, different crystal protein than Bacillus thuringiensis or a part thereof insecticide, such as the binary toxin consisting of the crystal proteins Cy34 and Cy35 (Moellenbeck et al., Nat. Biotechnol. (2001), 19, 668-72; Schnepf et al., Applied Environment Microb. (2006) 71, 1765-1774); or 3) an insecticidal hybrid protein comprising parts of two different insecticides of Bacillus thuringiensis crystal proteins, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g. For example, the protein Cry1A.105 produced by the corn event MON98034 (WO
2007/027777); oder 2007/027777); or
4) ein Protein gemäß einem der Punkte 1 ) bis 3) oben, in dem einige, 4) a protein according to any one of items 1) to 3) above, in which some,
insbesondere 1 bis 10, Aminosäuren durch eine andere Aminosäure ersetzt wurden, um eine höhere Insektizide Wirksamkeit gegenüber einer Zielinsektenart zu erzielen und/oder um das Spektrum der entsprechenden Zielinsektenarten zu erweitern und/oder wegen Veränderungen, die in die Kodier- DNA während der Klonierung oder Transformation induziert wurden, wie das Protein Cry3Bb1 in Mais-Events MON863 oder MON88017 oder das Protein Cry3A im Mais-Event MIR 604; oder In particular, 1 to 10, amino acids have been replaced by another amino acid to achieve higher insecticidal activity against a target insect species and / or to broaden the spectrum of the corresponding target insect species and / or due to changes in the coding DNA during cloning or Transformation were induced, such as the protein Cry3Bb1 in maize events MON863 or MON88017 or the protein Cry3A in the maize event MIR 604; or
5) ein Insektizides sezerniertes Protein aus Bacillus thuringiensis oder Bacillus cereus oder einen Insektiziden Teil davon, wie die vegetativ wirkenden 5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus or an insecticidal part thereof, such as the vegetative
insektentoxischen Proteine (vegetative insecticidal proteins, VIP), die unter folgendem Link angeführt sind, z. B. Proteine der Proteinklasse VIP3Aa: insecticidal proteins (VIP) listed under the following link, e.g. B. Proteins of protein class VIP3Aa:
http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/vip.html oder http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/vip.html or
6) ein sezerniertes Protein aus Bacillus thuringiensis oder Bacillus cereus, das in Gegenwart eines zweiten sezernierten Proteins aus Bacillus thuringiensis oder B. cereus Insektizid wirkt, wie das binäre Toxin, das aus den Proteinen VIP1A und VIP2A besteht (WO 94/21795); oder 6) a secreted protein from Bacillus thuringiensis or Bacillus cereus which acts in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus insecticide, such as the binary toxin consisting of the proteins VIP1A and VIP2A (WO 94/21795); or
7) ein Insektizides Hybridprotein, das Teile von verschiedenen sezernierten Proteinen von Bacillus thuringiensis oder Bacillus cereus umfaßt, wie ein Hybrid der Proteine von 1 ) oder ein Hybrid der Proteine von 2) oben; oder 7) an insecticidal hybrid protein comprising parts of various secreted proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins of 1) or a hybrid of the proteins of 2) above; or
8) ein Protein gemäß einem der Punkte 1 ) bis 3) oben, in dem einige, 8) a protein according to any one of items 1) to 3) above, in which some,
insbesondere 1 bis 10, Aminosäuren durch eine andere Aminosäure ersetzt wurden, um eine höhere Insektizide Wirksamkeit gegenüber einer Zielinsektenart zu erzielen und/oder um das Spektrum der entsprechenden Zielinsektenarten zu erweitern und/oder wegen Veränderungen, die in die Kodier- DNA während der Klonierung oder Transformation induziert wurden (wobei die Kodierung für ein Insektizides Protein erhalten bleibt), wie das Protein VIP3Aa im Baumwoll-Event COT 102. Natürlich zählt zu den insektenresistenten transgenen Pflanzen im vorliegenden Zusammenhang auch jegliche Pflanze, die eine Kombination von Genen umfaßt, die für die Proteine von einer der oben genannten Klassen 1 bis 8 kodieren. In einer Ausführungsform enthält eine insektenresistente Pflanze mehr als ein Transgen, das für ein Protein nach einer der oben genannten 1 bis 8 kodiert, um das Spektrum der entsprechenden Zielinsektenarten zu erweitern oder um die Entwicklung einer In particular, 1 to 10, amino acids have been replaced by another amino acid to achieve a higher insecticidal activity against a target insect species and / or to expand the spectrum of the corresponding target insect species and / or due to alterations induced in the coding DNA during cloning or transformation (preserving the coding for an insecticidal protein), such as the protein VIP3Aa in the cotton event COT 102. Of course, the insect-resistant transgenic plants in the present connection also any plant comprising a combination of genes coding for the proteins of any of the above classes 1 to 8. In one embodiment, an insect resistant plant contains more than one transgene encoding a protein of any one of the above 1 to 8 in order to extend the spectrum of the corresponding target insect species or to develop a protein
Resistenz der Insekten gegen die Pflanzen dadurch hinauszuzögern, dass man verschiedene Proteine einsetzt, die für dieselbe Zielinsektenart insektizid sind, jedoch eine unterschiedliche Wirkungsweise, wie Bindung an unterschiedliche To delay insect resistance to plants by using different proteins which are insecticidal for the same target insect species, but a different mode of action, such as binding to different ones
Rezeptorbindungsstellen im Insekt, aufweisen. Receptor binding sites in the insect.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind gegenüber abiotischen Streßfaktoren tolerant. Solche Pflanzen können durch genetische Compounds of general formula (I) are tolerant to abiotic stressors. Such plants can be caused by genetic
Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Streßresistenz verleiht, erhalten werden. Zu besonders nützlichen Pflanzen mit Streßtoleranz zählen folgende: a. Pflanzen, die ein Transgen enthalten, das die Expression und/oder Aktivität des Gens für die Poly(ADP-ribose)polymerase (PARP) in den Pflanzenzellen oder Transformation or by selection of plants containing a mutation conferring such stress resistance. Particularly useful plants with stress tolerance include the following: a. Plants which contain a transgene which have the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or
Pflanzen zu reduzieren vermag, wie dies in WO 2000/004173 oder EP 04077984.5 oder EP 06009836.5 beschrieben ist. b. Pflanzen, die ein streßtoleranzförderndes Transgen enthalten, das die  To reduce plants, as described in WO 2000/004173 or EP 04077984.5 or EP 06009836.5. b. Plants containing a stress tolerance-enhancing transgene which causes the
Expression und/oder Aktivität der für PARG kodierenden Gene der Pflanzen oderExpression and / or activity of the genes of the plants coding for PARG or
Pflanzenzellen zu reduzieren vermag, wie dies z.B. in WO 2004/090140 beschrieben ist; c. Pflanzen, die ein streßtoleranzförderndes Transgen enthalten, das für ein in Pflanzen funktionelles Enzym des Nicotinamidadenindinukleotid-Salvage- Biosynthesewegs kodiert, darunter Nicotinamidase, Can reduce plant cells, as described for example in WO 2004/090140; c. Plants which contain a stress tolerance enhancing transgene coding for a plant functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthetic pathway, including nicotinamidase,
Nicotinatphosphoribosyltransferase, Nicotinsäuremononukleotid-adenyltransferase, Nicotinamidadenindinukleotidsynthetase oder Nicotinamidphosphoribosyl-transferase, wie dies z. B. in EP 04077624.7 oder WO 2006/133827 oder PCT/EP07/002433 beschrieben ist.  Nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase, as described e.g. As described in EP 04077624.7 or WO 2006/133827 or PCT / EP07 / 002433.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
Verbindungen der allgemeinen Formel (!) behandelt werden können, weisen eine veränderte Menge, Qualität und/oder Lagerfähigkeit des Ernteprodukts und/oder veränderte Eigenschaften von bestimmten Bestandteilen des Ernteprodukts auf, wie zum Beispiel:  Compounds of general formula (I) may have an altered amount, quality and / or shelf life of the harvested product and / or altered properties of certain components of the harvested product, such as:
1 ) Transgene Pflanzen, die eine modifizierte Stärke synthetisieren, die bezüglich ihrer chemisch-physikalischen Eigenschaften, insbesondere des Amylosegehalts oder des Amylose/Amylopektin-Verhältnisses, des Verzweigungsgrads, der 1) Transgenic plants that synthesize a modified starch, with respect to their chemical-physical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the
durchschnittlichen Kettenlänge, der Verteilung der Seitenketten, des average chain length, the distribution of side chains, the
Viskositätsverhaltens, der Gelfestigkeit, der Stärkekorngröße und/oder Viscosity behavior, the gel strength, the starch grain size and / or
Stärkekornmorphologie im Vergleich mit der synthetisierten Stärke in Starch grain morphology in comparison with the synthesized starch in
Wildtyppflanzenzellen oder -pflanzen verändert ist, so dass sich diese modifizierte Stärke besser für bestimmte Anwendungen eignet. Diese transgenen Pflanzen, die eine modifizierte Stärke synthetisieren, sind zum Beispiel in EP 0571427, WO Wild-type plant cells or plants, so that this modified starch is better suited for certain applications. These transgenic plants synthesizing a modified starch are described, for example, in EP 0571427, WO
95/004826, EP 0719338, WO 96/15248, WO 96/19581 , WO 96/27674, WO 97/11 188, WO 97/26362, WO 97/32985, WO 97/42328, WO 97/44472, WO 97/45545, WO 98/27212, WO 98/40503, WO 99/58688, WO 99/58690, WO 99/58654, WO 95/004826, EP 0719338, WO 96/15248, WO 96/19581, WO 96/27674, WO 97/11188, WO 97/26362, WO 97/32985, WO 97/42328, WO 97/44472, WO 97 / 45545, WO 98/27212, WO 98/40503, WO 99/58688, WO 99/58690, WO 99/58654, WO
2000/008184, WO 2000/008185, WO 2000/28052, WO 2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059, WO 2003/071860, WO 2004/056999, WO 2000/008184, WO 2000/008185, WO 2000/28052, WO 2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059, WO 2003/071860, WO 2004/056999, WO
2005/030942, WO 2005/030941 , WO 2005/095632, WO 2005/095617, WO 2005/030942, WO 2005/030941, WO 2005/095632, WO 2005/095617, WO
2005/095619, WO 2005/095618, WO 2005/123927, WO 2006/018319, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO 2006/018319, WO
2006/103107, WO 2006/108702, WO 2007/009823, WO 2000/22140, WO 2006/103107, WO 2006/108702, WO 2007/009823, WO 2000/22140, WO
2006/063862, WO 2006/072603, WO 2002/034923, EP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1 , EP 07090009.7, WO 2001/14569, WO 2002/79410, WO 2003/33540, WO 2004/078983, WO 2001/19975, WO 95/26407, WO 96/34968, WO 98/20145, WO 99/12950, WO 99/66050, WO 99/53072, US 6,734,341 , WO 2000/1 1 192, WO 98/22604, WO 98/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359, US 5,824,790, US 6,013,861 , WO 94/004693, WO 94/009144, WO 94/1 1520, WO 95/35026 bzw. WO 97/20936 beschrieben. 2006/063862, WO 2006/072603, WO 2002/034923, EP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1, EP 07090009.7, WO 2001/14569, WO 2002/79410, WO 2003/33540, WO 2004/078983, WO 2001/19975, WO 95/26407, WO 96/34968, WO 98/20145, WO 99/12950, WO 99/66050, WO 99/53072, US Pat. No. 6,734,341, WO 2000 No. 1,192, WO 98/22604, WO 98/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359, US Pat. No. 5,824,790, US Pat. No. 6,013,861, WO 94/004693, WO 94/009144, WO 94/1 1520, WO 95/35026 and WO 97/20936, respectively.
2) Transgene Pflanzen, die Nichtstärkekohlenhydratpolymere synthetisieren, oder Nichtstärkekohlenhydratpolymere, deren Eigenschaften im Vergleich zu 2) Transgenic plants that synthesize non-starch carbohydrate polymers, or non-starch carbohydrate polymers whose properties are compared to
Wildtyppflanzen ohne genetische Modifikation verändert sind. Beispiele sind Pflanzen, die Polyfructose, insbesondere des Inulin- und Levantyps, produzieren, wie dies in EP 0663956, WO 96/001904, Wo 96/021023, WO 98/039460 und WO 99/024593 beschrieben ist, Pflanzen, die alpha-1 ,4-Glucane produzieren, wie dies in WO Wildtype plants are modified without genetic modification. Examples are plants which produce polyfructose, in particular of the inulin and levan type, as described in EP 0663956, WO 96/001904, Wo 96/021023, WO 98/039460 and WO 99/024593, plants which are alpha-1 To produce 4-glucans, as in WO
95/031553, US 2002/031826, US 6,284,479, US 5,712,107, WO 97/047806, WO 97/047807, WO 97/047808 und WO 2000/14249 beschrieben ist, Pflanzen, die alpha- 1 ,6-verzweigte alpha-1 ,4-Glucane produzieren, wie dies in WO 2000/73422 95/031553, US 2002/031826, US 6,284,479, US 5,712,107, WO 97/047806, WO 97/047807, WO 97/047808 and WO 2000/14249, plants which are alpha-1, 6-branched alpha-1 4-glucans, as described in WO 2000/73422
beschrieben ist, und Pflanzen, die Alternan produzieren, wie dies in WO 2000/047727, EP 06077301 .7, US 5,908,975 und EP 0728213 beschrieben ist. and plants which produce alternan, as described in WO 2000/047727, EP 06077301.7, US 5,908,975 and EP 0728213.
3) Transgene Pflanzen, die Hyaluronan produzieren, wie dies zum Beispiel in WO 06/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316, JP 2006/304779 und WO 2005/012529 beschrieben ist. 3) Transgenic plants which produce hyaluronan, as described, for example, in WO 06/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316, JP 2006/304779 and WO 2005/012529.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Pflanzen wie Baumwollpflanzen mit veränderten Fasereigenschaften . Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solche veränderten Fasereigenschaften verleiht, erhalten werden; dazu zählen: a) Pflanzen wie Baumwollpflanzen, die eine veränderte Form von Compounds of general formula (I) can be treated are plants such as cotton plants with altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; These include: a) plants, such as cotton plants, which have an altered form of
Cellulosesynthasegenen enthalten, wie dies in WO 98/000549 beschrieben ist, b) Pflanzen wie Baumwollpflanzen, die eine veränderte Form von rsw2- oder rsw3- homologen Nukleinsäuren enthalten, wie dies in WO 2004/0532 9 beschrieben ist; c) Pflanzen wie Baumwollpflanzen mit einer erhöhten Expression der Contain cellulose synthase genes, as described in WO 98/000549, b) plants, such as cotton plants, which contain an altered form of rsw2 or rsw3-homologous nucleic acids, as described in WO 2004/05329; c) plants such as cotton plants with an increased expression of the
Saccharosephosphatsynthase, wie dies in WO 2001/017333 beschrieben ist; d) Pflanzen wie Baumwollpflanzen mit einer erhöhten Expression der Sucrose phosphate synthase as described in WO 2001/017333; d) plants such as cotton plants with an increased expression of
Saccharosesynthase, wie dies in WO 02/45485 beschrieben ist; e) Pflanzen wie Baumwollpflanzen bei denen der Zeitpunkt der Durchlaßsteuerung der Plasmodesmen an der Basis der Faserzelle verändert ist, z. B. durch Sucrose synthase as described in WO 02/45485; e) plants such as cotton plants in which the timing of the passage control of the Plasmodesmen is changed at the base of the fiber cell, z. B. by
Herunterregulieren der faserselektiven ß-1 ,3-Glucanase, wie dies in WO 2005/017157 beschrieben ist; f) Pflanzen wie Baumwollpflanzen mit Fasern mit veränderter Reaktivität, z. B. durch Expression des N-Acetylglucosamintransferasegens, darunter auch nodC, und von Chitinsynthasegenen, wie dies in WO 2006/136351 beschrieben ist. Down-regulating the fiber-selective β-1,3-glucanase as described in WO 2005/017157; f) plants such as cotton plants with modified reactivity fibers, e.g. By expression of the N-acetylglucosamine transferase gene, including nodC, and chitin synthase genes, as described in WO 2006/136351.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Pflanzen wie Raps oder verwandte Brassica-Pflanzen mit veränderten Eigenschaften der  Compounds of general formula (I) can be treated are plants such as rapeseed or related Brassica plants with altered properties of
Ölzusammensetzung. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solche veränderten Öleigenschaften verleiht, erhalten werden; dazu zählen: a) Pflanzen wie Rapspflanzen, die Öl mit einem hohen Ölsäuregehalt produzieren, wie dies zum Beispiel in US 5,969,169, US 5,840,946 oder US 6,323,392 oder US 6,063, 947 beschrieben ist; b) Pflanzen wie Rapspflanzen, die Öl mit einem niedrigen Linolensäuregehalt produzieren, wie dies in US 6,270828, US 6,169,190 oder US 5,965,755 beschrieben ist. c) Pflanzen wie Rapspflanzen, die öl mit einem niedrigen gesättigten Fettsäuregehalt produzieren, wie dies z. B. in US 5,434,283 beschrieben ist. Besonders nützliche transgene Pflanzen, die mit den erfindungsgemäßen Oil composition. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; These include: a) plants such as rape plants that produce high oleic oil, as described, for example, in US 5,969,169, US 5,840,946 or US 6,323,392 or US 6,063,947; b) plants such as oilseed rape plants which produce low linolenic acid oil, as described in US 6,270,828, US 6,169,190 or US 5,965,755. c) plants such as rape plants, which produce oil with a low saturated fatty acid content, as z. As described in US 5,434,283. Particularly useful transgenic plants with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Pflanzen, die Transformations-Events, oder eine Kombination von Transformations-Events, enthalten und die zum Beispiel in den Dateien von verschiedenen nationalen oder regionalen Behörden angeführt sind.  Compounds of general formula (I) may be treated as plants containing transformation events, or a combination of transformation events, for example as listed in the files of various national or regional authorities.
Besonders nützliche transgene Pflanzen, die mit den erfindungsgemäßen Particularly useful transgenic plants with the inventive
Verbindungen der allgemeinen Formel (I) behandelt werden können, sind beispielhaft Pflanzen mit einem oder mehreren Genen, die für ein oder mehrere Toxine kodieren, sind die transgenen Pflanzen, die unter den folgenden Handelsbezeichnungen angeboten werden: YIELD GARD® (zum Beispiel Mais, Baumwolle, Sojabohnen), KnockOut® (zum Beispiel Mais), BiteGard® (zum Beispiel Mais), BT-Xtra® (zum Beispiel Mais), StarLink® (zum Beispiel Mais), Bollgard® (Baumwolle), Nucotn® (Baumwolle), Nucotn 33B® (Baumwolle), NatureGard® (zum Beispiel Mais), Exemplary plants having one or more genes encoding one or more toxins are the transgenic plants available under the following tradenames: YIELD GARD® (for example, corn, cotton , Soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example maize), StarLink® (for example corn), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn),
Protecta® und NewLeaf® (Kartoffel). Herbizidtolerante Pflanzen, die zu erwähnen sind, sind zum Beispiel Maissorten, Baumwollsorten und Sojabohnensorten, die unter den folgenden Handelsbezeichnungen angeboten werden: Roundup Ready® Protecta® and NewLeaf® (potato). Herbicide-tolerant crops to be mentioned include, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready®
(Glyphosatetoleranz, zum Beispiel Mais, Baumwolle, Sojabohne), Liberty Link® (Phosphinotricintoleranz, zum Beispiel Raps), IMI® (Imidazolinontoleranz) und SCS® (Sylfonylhamstofftoleranz), zum Beispiel Mais. Zu den herbizidresistenten Pflanzen (traditionell auf Herbizidtoleranz gezüchtete Pflanzen), die zu erwähnen sind, zählen die unter der Bezeichnung Clearfield® angebotenen Sorten (zum Beispiel Mais). (Glyphosate tolerance, for example corn, cotton, soybean), Liberty Link® (phosphinotricin tolerance, for example rapeseed), IMI® (imidazolinone tolerance) and SCS® (sylphonylurea tolerance), for example maize. Herbicide-resistant plants (plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfield® (for example corn).
Die erfindungsgemäß zu verwendenden Verbindungen der Formel (I) können in übliche Formulierungen überführt werden, wie Lösungen, Emulsionen, Spritzpulver, wasser- und ölbasierte Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, lösliche Granulate, Streugranulate, Suspensions-Emulsions-Konzentrate, Wirkstoff - imprägnierte Naturstoffe, Wirkstoff-imprägnierte synthetische Stoffe, Düngemittel sowie Feinstverkapselungen in polymeren Stoffen. Im Rahmen der vorliegenden Erfindung ist es insbesondere bevorzugt, wenn die Verbindungen der allgemeinen Formel (I) in der Form einer Sprühformulieruing verwendet werden. The compounds of the formula (I) to be used according to the invention can be converted into customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, Active substance - impregnated natural substances, active substance-impregnated synthetic substances, fertilizers and microencapsulation in polymeric substances. In the context of the present It is particularly preferred for the invention to use the compounds of general formula (I) in the form of a spray formulation.
Die vorliegende Erfindung betrifft daher darüber hinaus auch eine Sprühformulierung zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischem Stress. Im Folgenden wird eine Sprühformulierung näher beschrieben: The present invention therefore further relates to a spray formulation for increasing the resistance of plants to abiotic stress. In the following, a spray formulation is described in more detail:
Die Formulierungen zur Sprühapplikation werden in bekannter Weise hergestellt, z.B. durch Vermischen der erfindungsgemäß zu verwendenden Verbindungen der aligmeinen Formel (I) mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Weitere übliche Zusatzstoffe, wie zum Beispiel übliche Streckmittel sowie Lösungsoder Verdünnungsmittel, Farbstoffe, Netzmittel, Dispergiermittel, Emulgatoren, Entschäumer, Konservierungsmittel, sekundäre Verdickungsmittel, Kleber, The formulations for spray application are prepared in a known manner, e.g. by mixing the compounds of the formula (I) to be used according to the invention with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents. Other conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives,
Gibberelline und auch Wasser, können gegebenenfalls auch verwendet werden. Die Herstellung der Formulierungen erfolgt entweder in geeigneten Anlagen oder auch vor oder während der Anwendung. Als Hilfsstoffe können solche Stoffe Verwendung finden, die geeignet sind, dem Mittel selbst oder und/oder davon abgeleitete Zubereitungen (z.B. Spritzbrühen) besondere Eigenschaften zu verleihen, wie bestimmte technische Eigenschaften und/oder auch besondere biologische Eigenschaften. Als typische Hilfsmittel kommen in Frage:  Gibberellins and also water may also be used if necessary. The preparation of the formulations is carried out either in suitable systems or before or during use. Excipients which can be used are those which are suitable for imparting special properties to the composition itself or to preparations derived therefrom (for example spray mixtures), such as certain technical properties and / or special biological properties. As typical aids are:
Streckmittel, Lösemittel und Trägerstoffe. Extenders, solvents and carriers.
Als Streckmittel eignen sich z.B. Wasser, polare und unpolare organische chemische Flüssigkeiten z.B. aus den Klassen der aromatischen und nicht-aromatischen As extender, e.g. Water, polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic
Kohlenwasserstoffe (wie Paraffine, Alkylbenzole, Alkylnaphthaline, Chlorbenzole), der Alkohole und Polyole (die ggf. auch substituiert, verethert und/oder verestert sein können), der Ketone (wie Aceton, Cyclohexanon), Ester (auch Fette und Öle) und (Poly-)Ether, der einfachen und substituierten Amine, Amide, Lactame (wie N- Alkylpyrrolidone) und Lactone, der Sulfone und Sulfoxide (wie Dimethylsysulfoxid). Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösemittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösemittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkylnaphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethyl- keton, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), esters (including fats and oils) and ( Poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide). In the case of using water as extender, for example, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as
Dimethylsulfoxid, sowie Wasser. Dimethyl sulfoxide, as well as water.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferro- cyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyanin- farbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden. Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Als Netzmittel, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen, die Benetzung fördernden Stoffe in Frage. Vorzugsweise verwendbar sind Alkylnaphthalin-Sulfonate, wie Diisopropyl- oder Diisobutylnaphthalin-Sulfonate. Suitable wetting agents which may be present in the formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preferably usable are alkylnaphthalene sulfonates such as diisopropyl or diisobutylnaphthalene sulfonates.
Als Dispergiermittel und/oder Emulgatoren, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen nichtionischen, anionischen und kationischen Dispergiermittel in Betracht. Vorzugsweise verwendbar sind nichtionische oder anionische Dispergiermittel oder Gemische von nichtionischen oder anionischen Dispergiermitteln. Als geeignete nichtionische Dispergiermittel sind insbesondere Ethylenoxid- Propylenoxid-Blockpolymere, Alkylphenolpolyglykolether sowie Tristryrylphenol- polyglykolether und deren phosphatierte oder sulfatierte Derivate zu nennen. Geeignete anionische Dispergiermittel sind insbesondere Ligninsulfonate, Poly- acrylsäuresalze und Arylsulfonat-Formaldehydkondensate. Suitable dispersants and / or emulsifiers which may be present in the formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Particularly suitable nonionic dispersants are ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
Als Entschäumer können in den erfindungsgemäß verwendbaren Formulierungen alle zur Formulierung von agrochemischen Wirkstoffen üblichen schaumhemmenden Stoffe enthalten sein. Vorzugsweise verwendbar sind Silikonentschäumer und Magne- siumstearat. Defoamers which can be used in the formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds Be contained substances. Preference is given to using silicone defoamers and magnesium stearate.
Als Konservierungsmittel können in den erfindungsgemäß verwendbaren As preservatives can be used in the invention
Formulierungen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe vorhanden sein. Beispielhaft genannt seien Dichlorophen und Benzylalkohol- hemiformal. Formulations all substances that can be used for such purposes in agrochemical agents be present. Examples include dichlorophen and benzyl alcohol hemiformal.
Als sekundäre Verdickungsmittel, die in den erfindungsgemäß verwendbaren Formu- lierungen enthalten sein können, kommen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe in Frage. Vorzugsweise in Betracht kommen Cellulose- derivate, Acrylsäurederivate, Xanthan, modifizierte Tone und hochdisperse Kieselsäure. Als Kleber, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen alle üblichen in Beizmitteln einsetzbaren Bindemittel in Frage. Suitable secondary thickeners which may be present in the formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preferably suitable are cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica. Suitable adhesives which may be present in the formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
Vorzugsweise genannt seien Polyvinylpyrrolidon, Polyvinylacetat, Polyvinylalkohol und Tylose. Als Gibberelline, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen vorzugsweise die Gibberelline A1 , A3 (= Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose. As gibberellins which may be present in the formulations which can be used according to the invention, the gibberellins A1, A3 (=
Gibberellinsäure), A4 und A7 infrage, besonders bevorzugt verwendet man die Gibberellinic acid), A4 and A7 in question, particularly preferably using the
Gibberellinsäure. Die Gibberelline sind bekannt (vgl. R. Wegler„Chemie der Gibberellic acid. The gibberellins are known (see R. Wegler "Chemie der
Pflanzenschutz- und Schädlingsbekämpfungsmittel", Bd. 2, Springer Verlag, 1970, S. 401 -412). Weitere Additive können Duftstoffe, mineralische oder vegetabilische gegebenenfalls modifizierte Öle, Wachse und Nährstoffe (auch Spurennährstoffe), wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink sein. Weiterhin enthalten sein können Stabilisatoren wie Kältestabilisatoren, Oxidationsschutzmittel, Lichtschutzmittel oder andere die chemische und / oder physikalische Stabilität verbessernde Mittel. 2, Springer Verlag, 1970, pp. 401-412) Further additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also micronutrients), such as salts of iron, manganese, boron , Copper, cobalt, molybdenum and zinc, stabilizers such as low-temperature stabilizers, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents.
Die Formulierungen enthalten im allgemeinen zwischen 0,01 und 98 Gew.-%, vorzugsweise zwischen 0,5 und 90 %, der Verbindung der allgemeinen Formel (I). Die erfindungsgemäßen Verbindungen der aligemeinen Formel (I) können in handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit anderen Wirkstoffen wie Insektiziden, The formulations generally contain between 0.01 and 98% by weight, preferably between 0.5 and 90%, of the compound of general formula (I). The compounds of general formula (I) according to the invention can be prepared in commercial formulations and in the formulations prepared from these formulations in admixture with other active substances such as insecticides,
Lockstoffen, Sterilantien, Bakteriziden, Akariziden, Nematiziden, Fungiziden, wachstumsregulierenden Stoffen, Herbiziden, Safenern, Düngemitteln oder Attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or
Semiochemicals vorliegen. Semiochemicals are present.
Ferner lässt sich die beschriebene positive Wirkung der Verbindungen der Formel (I) auf die pflanzeneigenen Abwehrkräfte durch eine zusätzliche Behandlung mit insektziden, fungiziden oder bakteriziden Wirkstoffen unterstützen. Furthermore, the described positive effect of the compounds of the formula (I) on the plant's own defenses can be assisted by additional treatment with insecticidal, fungicidal or bactericidal active substances.
Bevorzugte Zeitpunkte für die Applikation der erfindungsgemäß zu verwendenden Verbindungen der allgemeinen Formel (I) oder deren Salze zur Steigerung der Resistenz gegenüber abiotischem Stress sind Boden-, Stamm- und/oder Preferred times for the application of the compounds of the general formula (I) to be used according to the invention or their salts for increasing the resistance to abiotic stress are soil, parent and / or
Blattbehandlungen mit den zugelassenen Aufwandmengen. Leaf treatments with the approved application rates.
Die erfindungsgemäß zu verwendenden Wirkstoffe der allgemeinen Formel (I) oder deren Salze können im Allgemeinen darüber hinaus in ihren handelsüblichen The active compounds of the general formula (I) or salts thereof to be used according to the invention can generally also be used in their commercial form
Formulierungen sowie in den aus diesen Formulierungen bereiteten Formulations and in those prepared from these formulations
Anwendungsformen in Mischungen mit anderen Wirkstoffen, wie Insektiziden, Lockstoffen, Sterilantien, Akariziden, Nematiziden, Fungiziden, Bakteriziden, wachstumsregulierenden Stoffen, die Pflanzenreife beeinflussenden Stoffen, Safenern oder Herbiziden vorliegen. Besonders günstige Mischpartner sind beispielsweise die nachfolgend gruppenweise genannten Wirkstoffe der verschiedenen Klassen, ohne dass durch deren Reihenfolge eine Präferenz gesetzt wird: Use forms in mixtures with other active ingredients, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, bactericides, growth-regulating substances, the plant ripeness affecting substances, safeners or herbicides are present. Particularly favorable mixing partners are, for example, the active substances of the various classes which are mentioned below in groups, without preference being given to their order:
Fungizide: fungicides:
F1 ) Inhibitoren der Nucleinsäure Synthese, z. B. Benalaxyl, Benalaxyl-M, Bupirimat, Chiralaxyl, Clozylacon, DimethirimoS, Ethirimol, Furaiaxyl, Hymexazol, Metalaxyl, Metalaxyl-M, Ofurace, Oxadixyl, Oxolinsäure; F1) inhibitors of nucleic acid synthesis, e.g. Benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon, dimethirimo S, ethirimol, furaiaxyl, hymexazole, metalaxyl, metalaxyl-M, ofurace, oxadixyl, oxolinic acid;
F2) Inhibitoren der Mitose und Zellteilung, z. B. Benomyl, Carbendazim, Diethofencarb, Fuberidazole, Fluopicolid, Pencycuron, Thiabendazol, Thiophanat-methyl, Zoxamid und Chlor-7-(4-methylpiperidin-1-yl)-6-(2,4,6- Trifluorphenyl [1 ,2,4]triazolo[1 ,5- ajpyrimidin; F2) inhibitors of mitosis and cell division, e.g. Benomyl, carbendazim, diethofencarb, fuberidazole, fluopicolide, pencycuron, thiabendazole, thiophanate-methyl, zoxamide and chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1, 2 , 4] triazolo [1,5-ajpyrimidine;
F3) Inhibitoren der Atmungskette Komplex I / II, z. B. Diflumetorim, Bixafen, Boscalid, Carboxin, Diflumethorim Fenfuram, Fluopyram, Flutolanil, Furametpyr, Mepronil, Oxycarboxin, Penflufen, Penthiopyrad, Thifluzamid, N-[2-(1 ,3-Dimethylbutyl)phenyl]-5- fluor-1 ,3-dimethyl-1 H-pyrazol-4-carboxamid, Isopyrazam, Sedaxan, 3-(Difluormethyl)- 1 -methyl-N-(3',4',5'-trifluorbiphenyl-2-yl)-1 H-pyrazol-4-carboxamid, 3-(Difluormethyl)-1- methyl-N-[2-(1 ,1 ,2,2-tetrafluorethoxy)phenyl]-1 H-pyrazol-4-carboxamid, 3- (Difluormethyl)-N-[4-fluoro-2-(1 ,1 ,2,3,3,3-hexafluorpropoxy)phenyl]-1 -methyl-1 H- pyrazol-4-carboxamid, N-[1 -(2,4-Dichlorphenyl)-1 -methoxypropan-2-yl]-3- (difluormethyl)-l -methyl-1 H-pyrazol-4-carboxamid und entsprechende Salze; F3) inhibitors of the respiratory chain complex I / II, z. Diflumetorim, bixafen, boscalid, carboxin, diflumethorim fenfuram, fluopyram, flutolanil, furametpyr, mepronil, oxycarboxin, penflufen, penthiopyrad, thifluzamide, N- [2- (1, 3-dimethylbutyl) phenyl] -5-fluoro-1, 3-dimethyl-1H-pyrazole-4-carboxamide, isopyrazam, sedaxane, 3- (difluoromethyl) -1-methyl-N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -1H-pyrazole 4-carboxamide, 3- (difluoromethyl) -1-methyl-N- [2- (1, 1, 2,2-tetrafluoroethoxy) phenyl] -1H-pyrazole-4-carboxamide, 3- (difluoromethyl) -N - [4-fluoro-2- (1,1,3,3,3,3-hexafluoropropoxy) phenyl] -1-methyl-1H-pyrazole-4-carboxamide, N- [1- (2,4-dichlorophenyl ) -1-methoxypropan-2-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide and corresponding salts;
F4) Inhibitoren der Atmungskette Komplex III, z. B.Amisulbrom, Azoxystrobin, F4) inhibitors of the respiratory chain complex III, z. B. amisulbrom, azoxystrobin,
Cyazofamid, Dimoxystrobin, Enestrobin, Famoxadon, Fenamidon, Fluoxastrobin, Kresoximmethyl, Metominostrobin, Orysastrobin, Pyraclostrobin, Pyribencarb, Cyazofamide, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoximethyl, metominostrobin, orysastrobin, pyraclostrobin, pyribencarb,
Picoxystrobin, Trifloxystrobin, (2E)-2-(2-{[6-(3-Chlor-2-methylphenoxy)-5- fluorpyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamid, (2E)-2- (Ethoxyimino)-N-methyl-2-(2-{[({(1 E)-1 -[3-(trifluoromethyl)- phenyl]ethyliden}amino)oxy]methyl}phenyl)ethanamid und entsprechende Salze, (2E)- 2-(Methoxyimino)-N-methyl-2-{2-[(E)-({1 -[3-(trifluormethyl)phenyl]ethoxy}- imino)methyl]phenyl}ethanamid, (2E)-2-{2-[({[(1 E)-1 -(3-{[(E)-1 -Fluor-2-phenylethenyl]- oxy}phenyl)ethyliden]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamid, (2E)-2-{2-[({[(2E,3E)-4-(2,6-Dichlorophenyl)but-3-en-2- yliden]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamid, 2-Chlor-N- (1 ,1 ,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)pyridin-3-carboxamid, 5-Methoxy-2-methyl- 4-(2-{[({( E)-1 -[3-(trifluormethyl)pheny!]ethyliden}amino)oxy]methyl}phenyl)-2,4- dihydro-3H-1 ,2,4-triazol-3-on, 2-Methyl-{2-[({cyclopropyl[(4-methoxyphenyl)- imino]methyl}sulfanyl)methyl]phenyl}-3-methoxyacrylat, N-(3-Ethyl-3,5,5- trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamid und entsprechende Salze; Picoxystrobin, trifloxystrobin, (2E) -2- (2 - {[6- (3-chloro-2-methylphenoxy) -5-fluoropyrimidin-4-yl] oxy} phenyl) -2- (methoxyimino) -N-methylethanamide, (2E) -2- (ethoxyimino) -N-methyl-2- (2 - {[({(1E) -1 - [3- (trifluoromethyl) phenyl] ethylidene} amino) oxy] methyl} phenyl) ethanamide and corresponding salts, (2E) -2- (methoxyimino) -N-methyl-2- {2 - [(E) - ({1- [3- (trifluoromethyl) phenyl] ethoxy} - imino) methyl] phenyl} ethanamide , (2E) -2- {2 - [({[(1 E) -1 - (3 - {[(E) -1-fluoro-2-phenylethenyl] oxy} phenyl) ethylidene] amino} oxy) methyl ] phenyl} -2- (methoxyimino) -N-methylethaneamide, (2E) -2- {2 - [({[(2E, 3E) -4- (2,6-dichlorophenyl) -but-3-en-2-] yliden] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N-methylethaneamide, 2-chloro-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl ) pyridine-3-carboxamide, 5-methoxy-2-methyl 4- (2 - {[({(E) -1 - [3- (trifluoromethyl) phenyl] ethylidene} amino) oxy] methyl} phenyl) -2,4-dihydro-3H-1,2,4-triazole 3-one, 2-methyl {2 - [({cyclopropyl [(4-methoxyphenyl) imino] methyl} sulfanyl) methyl] phenyl} -3-methoxyacrylate, N- (3-ethyl-3,5,5 trimethylcyclohexyl) -3- (formylamino) -2-hydroxybenzamide and corresponding salts;
F5) Entkoppler, z. B. Dinocap, Fluazinam; F5) decoupler, z. Dinocap, fluazinam;
F6) Inhibitoren der ATP Produktion, z. B. Fentinacetat, Fentinchlorid, Fentinhydroxid, Silthiofam F6) inhibitors of ATP production, e.g. Fentin acetate, fentin chloride, fentin hydroxide, silthiofam
F7) Inhibitoren der Aminosäure- und Proteinbiosynthese, z.B. Andoprim, Blasticidin-S, Cyprodinil, Kasugamycin, Kasugamycinhydrochlorid Hydrat, Mepanipyrim, F7) inhibitors of amino acid and protein biosynthesis, e.g. Andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim,
Pyrimethanil F8) Inhibitoren der Signal-Transduktion, z. B. Fenpiclonil, Fludioxonil, Quinoxyfen Pyrimethanil F8) inhibitors of signal transduction, e.g. Fenpiclonil, fludioxonil, quinoxyfen
F9) Inhibitoren der Fett- und Membran Synthese, z. B. Chlozolinat, Iprodion, F9) inhibitors of fat and membrane synthesis, e.g. B. chlozolinate, iprodione,
Procymidon, Vinclozolin, Ampropylfos, Kalium-Ampropylfos, Edifenphos, Iprobenfos (IBP), Isoprothiolan, Pyrazophos, Tolclofos-methyl, Biphenyl, lodocarb, Propamocarb, Propamocarb hydrochlorid Procymidone, Vinclozolin, Ampropylfos, Potassium-Ampropylfos, Edifenphos, Iprobenfos (IBP), Isoprothiolane, Pyrazophos, Tolclofos-methyl, Biphenyl, iodocarb, Propamocarb, Propamocarb hydrochloride
F10) Inhibitoren der Ergosterol Biosynthese, z. B. Fenhexamid, Azaconazol, Bitertanol, Bromuconazol, Diclobutrazol, Difenoconazol, Diniconazol, Diniconazol-M, Etaconazol, Fenbuconazol, Fluquinconazol, Flusilazol, Flutriafol, Furconazol, Furconazol-cis, Hexaconazol, Imibenconazol, Ipconazol, Metconazol, Myclobutanil, Paclobutrazol, Penconazol, Propiconazol, Prothioconazol, Simeconazol, Spiroxamin, Tebuconazol, Triadimefon, Triadimenol, Triticonazol, Uniconazol, Voriconazol, Imazalil, F10) inhibitors of ergosterol biosynthesis, eg. Fenhexamid, azaconazole, bitertanol, bromuconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, penconazole, Propiconazole, Prothioconazole, Simeconazole, Spiroxamine, Tebuconazole, Triadimefon, Triadimenol, Triticonazole, Uniconazole, Voriconazole, Imazalil,
Imazalilsulfat, Oxpoconazol, Fenarimol, Flurprimidol, Nuarimol, Pyrifenox, Triforin, Pefurazoat, Prochloraz, Triflumizol, Viniconazol, Aldimorph, Dodemorph, Imazalil sulfate, oxpoconazole, fenarimol, flurprimidol, nuarimol, pyrifenox, triforin, pefurazoate, prochloraz, triflumizole, viniconazole, aldimorph, dodemorph,
Dodemorphacetat, Fenpropimorph, Tridemorph, Fenpropidin, Naftifin, Pyributicarb, Terbinafin, 1 -(4-Chlorophenyl)-2-(1 H-1 ,2,4-triazol-1 -yl)cycloheptanol, Methyl-1 -(2,2- dimethyl-2,3-dihydro-1 H-inden-1 -yl)-1 H-imidazol-5-carboxylat, N'-{5-(Difluormethyl)-2- methyl-4-[3-(trimethyl-silyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamid, N-Ethyl- N-methyl-N'-{2-methyl-5-(trifluormethyl)-4-[3- (trimethylsilyl)propoxy]phenyl}imidoformamid und 0-{1 -[(4-Methoxy-phenoxy)methyl]-Dodemorphoacetate, fenpropimorph, tridemorph, fenpropidin, naftifine, pyributicarb, terbinafine, 1- (4-chlorophenyl) -2- (1H-1, 2,4-triazol-1-yl) cycloheptanol, methyl-1 - (2,2 dimethyl-2,3-dihydro-1H-inden-1-yl) -1H-imidazole-5-carboxylate, N '- {5- (difluoromethyl) -2-methyl-4- [3- (trimethyl- silyl) propoxy] phenyl} -N-ethyl-N-methylimidoformamide, N-ethyl-N-methyl-N '- {2-methyl-5- (trifluoromethyl) -4- [3- (trimethylsilyl) propoxy] phenyl} imidoformamide and 0- {1 - [(4-methoxyphenoxy) methyl] -
2.2- dimethy!propyl}-1 H-imidazol- -carbothioat; 2.2-dimethypropyl} -1H-imidazole-carbothioate;
F1 1 ) Inhibitoren der Zellwand Synthese, z. B. Benthiavalicarb, Bialaphos, F1 1) inhibitors of cell wall synthesis, e.g. Benthiavalicarb, Bialaphos,
Dimethomorph, Flumorph, Iprovalicarb, Polyoxins, Polyoxorim, Validamycin A Dimethomorph, flumorph, iprovalicarb, polyoxins, polyoxorim, validamycin A
F12) Inhibitoren der Melanin Biosynthese, z. B. Capropamid, Diclocymet, Fenoxanil, Phtalid, Pyroquilon, Tricyclazol F13) Resistenzinduktion, z. B. Acibenzolar-S-methyl, Probenazol, Tiadinil F12) inhibitors of melanin biosynthesis, e.g. Capropamide, diclocymet, fenoxanil, phtalid, pyroquilone, tricyclazole F13) resistance induction, e.g. Acibenzolar-S-methyl, probenazole, tiadinil
F14) Multisite, z. B. Captafol, Captan, Chlorothalonil, Kupfersalze wie: Kupferhydroxid, Kupfernaphthenat, Kupferoxychlorid, Kupfersulfat, Kupferoxid, Oxin-Kupfer und Bordeaux Mischung, Dichlofluanid, Dithianon, Dodin, Dodin freie Base, Ferbam, Folpet, Fluorofolpet, Guazatin, Guazatinacetat, Iminoctadin, Iminoctadinalbesilat,F14) Multisite, z. B. Captafol, captan, chlorothalonil, copper salts such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture, Dichlofluanid, Dithianon, Dodin, Dodin free base, Ferbam, Folpet, Fluorofolpet, Guazatin, Guazatinacetat, iminoctadine, Iminoctadinalbesilat,
Iminoctadintriacetat, Mankupfer, Mancozeb, Maneb, Metiram, Metiram Zink, Propineb, Schwefel und Schwefelpräparate enthaltend Calciumpolysulphid, Thiram, Tolylfluanid, Zineb, Ziram F15) Unbekannter Mechanismus, z. B. Amibromdol, Benthiazol, Bethoxazin, Iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, propineb, sulfur and sulfur preparations containing calcium polysulphide, thiram, tolylfluanid, zineb, ziram F15) Unknown mechanism, e.g. Amibromdole, benthiazole, bethoxazine,
Capsimycin, Carvon, Chinomethionat, Chloropicrin, Cufraneb, Cyflufenamid, Capsimycin, carvone, quinomethionate, chloropicrin, cufraneb, cyflufenamid,
Cymoxanil, Dazomet, Debacarb, Diclomezine, Dichlorophen, Dicloran, Difenzoquat, Difenzoquat Methylsulphat, Diphenylamin, Ethaboxam, Ferimzon, flumetover, Cymoxanil, Dazomet, Debacarb, Diclomezine, Dichlorophene, Dicloran, Difenzoquat, Difenzoquat Methylsulphate, Diphenylamine, Ethaboxam, Ferimzone, Flumetover,
Flusulfamid, Fluopicolid, Fluoroimid, Fosatyl-Al, Hexachlorobenzol, 8-Hydroxy- chinolinsulfat, Iprodione, Irumamycin, Isotianil, Methasulphocarb, Metrafenon, Methyl Isothiocyanat, Mildiomycin, Natamycin, Nickel dimethyldithiocarbamat, Nitrothal- isopropyl, Octhilinon, Oxamocarb, Oxyfenthiin, Pentachlorophenol und Salze, 2- Phenylphenol und Salze, Piperalin, Propanosin -Natrium, Proquinazid, Pyrrolnitrin, Quintozen, Tecloftalam, Tecnazen, Triazoxid, Trichlamid, Zarilamid und 2,3,5,6- Tetrachlor-4-(methylsulfonyl)-pyridin, N-(4-Chlor-2-nitrophenyl)-N-ethyl-4-methyl- benzenesulfonamid, 2-Amino-4-methyl-N-phenyl-5-thiazolecarboxamid, 2-Chlor-N- (2,3-dihydro-1 ,1 ,3-trimethyl-1 H-inden-4-yl)-3-pyridincarboxamid, 3-[5-(4-Chlorphenyl)-Flusulfamide, fluopicolide, fluoroimide, fosatyl-Al, hexachlorobenzene, 8-hydroxyquinoline sulfate, iprodione, irumamycin, isotianil, methasulphocarb, metrafenone, methyl isothiocyanate, mildiomycin, natamycin, nickel dimethyldithiocarbamate, nitrothal isopropyl, octhilinone, oxamocarb, oxyfenthiine, pentachlorophenol and Salts, 2-phenylphenol and salts, piperaline, propanosine sodium, proquinazide, pyrroline nitrate, quintozene, tecloftalam, tecnazene, triazoxide, trichlamide, zarilamide and 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine, N- (4-Chloro-2-nitrophenyl) -N-ethyl-4-methyl-benzenesulfonamide, 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide, 2-chloro-N- (2,3-dihydro-1 , 1, 3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide, 3- [5- (4-chlorophenyl) -
2.3- dimethylisoxazolidin-3-yl]pyridin, cis-1 -(4-Chlorphenyl)-2-(1 H-1 ,2,4-triazol-1 -yl)- cycloheptanol, 2,4-Dihydro-5-methoxy-2-methyl-4-[[[[1-[3-(trifluoromethyl)-phenyl]- ethyliden]-amino]-oxy]-methy!]-pheny!]-3H-1 ,2,3-triazol-3-on (185336-79-2), Methyl 1- (2,3-dihydro-2,2-dimethyl-1 H-inden-1 -yl)-1 H-imidazole-5-carboxylat, 3,4,5-Trichlor-2,6- pyridindicarbonitril, Methyl 2-[[[cyclopropyl[(4-methoxyphenyl) 2,3-dimethylisoxazolidin-3-yl] pyridine, cis-1 - (4-chlorophenyl) -2- (1H-1, 2,4-triazol-1-yl) -cycloheptanol, 2,4-dihydro-5-methoxy -2-methyl-4 - [[[[1- [3- (trifluoromethyl) phenyl] - ethylidene] amino] oxy] methyl] phenyl] - 3H-1,2,3-triazol-3-one (185336-79-2), methyl 1- (2,3-dihydro-2, 2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate, 3,4,5-trichloro-2,6-pyridinedicarbonitrile, methyl 2 - [[[cyclopropyl [(4-methoxyphenyl)
imino]methyl]thio]methyl]-. alpha. -(methoxymethylen)- benzacetat, 4-Chlor-alpha- propinyloxy-N-[2-[3-methoxy-4-(2-propinyloxy)phenyl]ethyl]-benzacetamide, (2S)-N-[2- [4-[[3-(4-chlorophenyl)-2-propinyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methyl- sulfonyl)amino]-butanamid, 5-Chlor-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)- [1 ,2,4]triazolo[1 ,5-a]pyrimidin, 5-Chlor-6-(2,4,6-trifluorophenyl)-N-[(1 R)-1 ,2,2-trimethyl- propyl][ ,2,4]triazolo[1 ,5-a]pyrimidin-7-amin, 5-Chlor-N-[(1 R)-1 ,2-dimethylpropyl]-6- (2,4,6-trifluorophenyl) [1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-amine, N-[1 -(5-Brom-3-chloro- pyridin-2-yl)ethyl]-2,4-dichloronicotinamid, N-(5-Brom-3-chlorpyridin-2-yl)methyl-2,4- dichlornicotinamid, 2-Butoxy-6-iod-3-propyl-benzopyranon-4-on, N-{(Z)-[(cyclopropyl- methoxy) imino][6-(difluormethoxy)-2,3-difluorphenyl]methyl}-2-benzacetamid, N-(3- Ethyl-3,5,5-trimethyl-cyclohexyl)-3-formylamino-2-hydroxy-benzamid, 2-[[[[1 -[3(1 Fluor- 2-phenylethyl)oxy] phenyl] ethyliden]amino]oxy]methyl]-alpha-(methoxyimino)-N- methyl-alphaE-benzacetamid, N-{2-[3-Chlor-5-(trifluormethyl)pyridin-2-yl]ethyl}-2- (trifluoromethyl)benzamid, N-(3',4'-dichlor-5-fluorbiphenyl-2-yl)-3-(difluormethyl)-1- methyl-1 H-pyrazol-4-carboxamid, N-(6-Methoxy-3-pyridinyl)-cyclopropan carboxamid, 1 -[(4-Methoxyphenoxy)methyl]-2,2-dimethylpropyl-1 H-imidazol-1- carbonsäure, O-[1 - [(4-Methoxyphenoxy)methyl]-2,2-dimethylpropyl]-1 H-imidazol- 1 - carbothioic acid, 2-(2- {[6-(3-Chlor-2-methylphenoxy)-5-fluorpyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N- methylacetamid imino] methyl] thio] methyl] -. alpha. - (methoxymethylene) - benzoacetate, 4-chloro-alpha-propynyloxy-N- [2- [3-methoxy-4- (2-propynyloxy) phenyl] ethyl] -benzacetamide, (2S) -N- [2- [4 - [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2 - [(methylsulfonyl) amino] butanamide, 5-chloro-7- (4 -methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine, 5-chloro-6- (2,4,6-) trifluorophenyl) -N - [(1 R) -1, 2,2-trimethyl-propyl] [, 2,4] triazolo [1,5-a] pyrimidin-7-amine, 5-chloro-N - [(1 R) -1,2-dimethylpropyl] -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidin-7-amine, N- [1- (5- Bromo-3-chloropyridin-2-yl) ethyl] -2,4-dichloronicotinamide, N- (5-bromo-3-chloropyridin-2-yl) methyl-2,4-dichloronotinotin, 2-butoxy-6- iodo-3-propylbenzopyranon-4-one, N - {(Z) - [(cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-benzacetamide, N- ( 3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide, 2 - [[[[1 - [3 (1-fluoro-2-phenylethyl) oxy] phenyl] ethylidene] amino ] oxy] methyl] -alpha- (methoxyimino) -N-methyl-alpha-E-benzoacetamide, N- {2- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] ethyl} -2- (trifluoromethyl) benzamide, N- (3 ', 4'-dichloro -5-fluorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, N- (6-methoxy-3-pyridinyl) -cyclopropane carboxamide, 1 - [(4- Methoxyphenoxy) methyl] -2,2-dimethylpropyl-1H-imidazole-1-carboxylic acid, O- [1- [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl] -1H-imidazole-1-carbothioic acid , 2- (2- {[6- (3-Chloro-2-methylphenoxy) -5-fluoropyrimidin-4-yl] oxy} phenyl) -2- (methoxyimino) -N-methylacetamide
Bakterizide: bactericides:
Bronopol, Dichiorophen, Nitrapyrin, Nickel-Dimethyldithiocarbamat, Kasugamycin, Octhilinon, Furancarbonsäure, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, Kupfersulfat und andere Kupfer-Zubereitungen. Bronopol, dichiorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.
Insektizide / Akarizide / Nematizide: Insecticides / acaricides / nematicides:
11 ) Acetylcholinesterase (AChE) Inhibitoren, wie beispielsweise Carbamate, z.B. 11) Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g.
Alanycarb, Aidicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carb- aryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thio- dicarb, Thiofanox, Triazamate, Trimethacarb, XMC und Xylylcarb; oder Alanycarb, Aidicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxim, Carb aryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamates, trimethacarb, XMC and xylylcarb; or
Organophosphate, z.B. Acephate, Azamethiphos, Azinphos (-methyl, -ethyl), Organophosphates, e.g. Acephates, azamethiphos, azinphos (-methyl, -ethyl),
Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos (-methyl), Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos (-methyl), Coumaphos, Cyanophos, Demeton-S-methyl, Diazinone, Dichlorvos / DDVP,
Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Isofenphos, Isopropyl O-(methoxyaminothio-phosphoryl) salicylat, Isoxathion, Malathion, Me- carbam, Methamidophos, ethidathion, Mevinphos, Monocrotophos, Naled, Dicrotophos, dimethoates, dimethylvinphos, disulphoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthione, fosthiazate, heptenophos, isofenphos, isopropyl O- (methoxyaminothio-phosphoryl) salicylate, isoxathione, malathion, mec-carbam, methamidophos, ethidathione, Mevinphos, Monocrotophos, Naled,
Omethoate, Oxydemeton-methyl, Parathion (-methyl), Phenthoate, Phorate, Omethoate, Oxydemeton-methyl, Parathion (-methyl), Phenthoate, Phorate,
Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos (-methyl), Profenofos, Pro- petamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Phosalone, Phosmet, Phosphamidone, Phoxim, Pirimiphos (-methyl), Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep,
Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon und Vamidothion. Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometone, Triazophos, Triclorfon and Vamidothion.
12) GABA-gesteuerte Chlorid-Kanal-Antagonisten, wie beispielsweise Organochiorine, z.B. Chlordane und Endosulfan (alpha-); oder Fiprole (Phenylpyrazole), z.B. Ethiprole, Fipronil, Pyrafluprole und Pyriprole. 12) GABA-controlled chloride channel antagonists, such as organo-chiorines, e.g. Chlordane and endosulfan (alpha); or fiproles (phenylpyrazoles), e.g. Ethiprole, Fipronil, Pyrafluprole and Pyriprole.
13) Natrium-Kanal-Modulatoren / Spannungsabhängige Natrium-Kanal-Blocker, wie beispielsweise Pyrethroide, z.B. Acrinathrin, Allethrin (d-cis-trans, d-trans), Bifenthrin, Bioallethrin, Bioallethrin-S-cyclopentenyl, Bioresmethrin, Cycloprothrin, Cyfluthrin (beta-), Cyhalothrin (gamma-, lambda-), Cypermethrin (alpha-, beta-, theta-, zeta-), Cy- phenothrin [(1 R)-fra/7s-lsomere], Deltamethrin, Dimefluthrin, Empenthrin [(EZ)-(1 R)- Isomere], Esfenvalerate, Etofenprox, Fenpropathrin, Fenvalerate, Flucythrinate, Flu- methrin, Fluvalinate (tau-), Halfenprox, Imiprothrin, Metofluthrin, Permethrin, Phenothrin [(1 f?)-trans-lsomer], Prallethrin, Profluthrin, Pyrethrine (pyrethrum), Resmethrin, RU 15525, Silafluofen, Tefluthrin, Tetra methrin [(1 R)- Isomere], Tralomethrin, 13) Sodium channel modulators / voltage dependent sodium channel blockers such as pyrethroids, e.g. Acrinathrin, allethrin (d-cis-trans, d-trans), bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin (beta-), cyhalothrin (gamma, lambda), cypermethrin (alpha-, beta , theta, zeta), cychenothrin [(1R) -fra / 7s isomers], deltamethrin, dimefluthrin, empenthrin [(EZ) (1R) isomers], esfenvalerates, etofenprox, fenpropathrin, fenvalerates , Flucythrinates, flumethrin, fluvalinates (tau-), halfenprox, imiprothrin, metofluthrin, permethrin, phenothrin [(1 f) trans-isomer], prallethrin, profuthrin, pyrethrins (pyrethrum), resmethrin, RU 15525, silafluofen, Tefluthrin, tetra methrin [(1R) - isomers], tralomethrin,
Transfluthrin und ZXI 8901 ; oder DDT; oder Methoxychlor. Transfluthrin and ZXI 8901; or DDT; or methoxychlor.
14) Nikotinerge Acetylcholin-Rezeptor-Agonisten, wie beispielsweise Neonikotinoide, z.B. Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid, Thiamethoxam; oder Nikotin. I5) Allosierische Aceiylcholin-Rezeptor-ModuSatoren (Agonisien), wie beispielsweise Spinosyne, z.B. Spinetoram und Spinosad. 16) Chlorid-Kanal-Aktivatoren, wie beispielsweise Avermectine/Milbemycine, z.B. 14) nicotinergic acetylcholine receptor agonists, such as neonicotinoids, eg, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; or nicotine. I5) Allocating aceiylcholine receptor moduators (agonists), such as spinosyns, eg spinetoram and spinosad. 16) chloride channel activators, such as avermectins / milbemycins, eg
Abamectin, Emamectin, Emamectin-benzoate, Lepimectin und Milbemectin. Abamectin, Emamectin, Emamectin benzoate, Lepimectin and Milbemectin.
17) Juvenilhormon-Analoge, z.B. Hydroprene, Kinoprene, Methoprene; oder 17) Juvenile hormone analogs, e.g. Hydroprene, kinoprene, methoprene; or
Fenoxycarb; Pyriproxyfen. fenoxycarb; Pyriproxyfen.
18) Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen, wie beispielsweise Begasungsmittel, z.B. Methylbromid und andere Alkylhalogenide; oder Chloropicrin; Sulfurylfluorid; Borax; Brechweinstein. 19) Selektive Fraßhemmer, z.B. Pymetrozine; oder Flonicamid. 18) Active ingredients with unknown or non-specific mechanisms of action, such as fumigants, e.g. Methyl bromide and other alkyl halides; or chloropicrin; sulfuryl fluoride; Borax; Tartar emetic. 19) Selective feeding inhibitors, e.g. pymetrozine; or flonicamide.
110) Milbenwachstumsinhibitoren, z.B. Clofentezine, Diflovidazin, Hexythiazox, Etoxazole. 11 1 ) Mikrowelle Disruptoren der Insektendarmmembran, wie beispielsweise Bacillus thuringiensis Subspezies israelensis, Bacillus sphaericus, Bacillus thuringiensis Subspezies aizawai, Bacillus thuringiensis Subspezies kurstaki, Bacillus thuringiensis Subspezies tenebrionis, und BT-Pflanzen-Proteine, z.B. CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1 . 110) mite growth inhibitors, e.g. Clofentezine, diflovidazine, hexythiazox, etoxazole. 11 1) Microwave disruptors of the insect gut membrane, such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plant proteins, e.g. CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1.
112) Inhibitoren der oxidativen Phosphorylierung, ATP-Disruptoren, wie beispielsweise Diafenthiuron; oder Organozinnverbindungen, z.B. Azocyclotin, Cyhexatin, Fenbutatin oxide; oder Propargite; Tetrad ifon. 113) Entkoppler der oxidativen Phoshorylierung durch Unterbrechung des H-Proton- gradienten, wie beispielsweise Chlorfenapyr und DNOC. 112) inhibitors of oxidative phosphorylation, ATP disruptors such as diafenthiuron; or organotin compounds, e.g. Azocyclotine, cyhexatin, fenbutatin oxide; or propargite; Tetrad ifon. 113) Decoupling of oxidative phosphorylation by interruption of the H proton gradient, such as chlorfenapyr and DNOC.
114) Nikotinerge Acetylcholin-Rezeptor-Antagonisten, wie beispielsweise Bensultap, Cartap (-Hydrochlorid), Thiocyclam, und Thiosultap (-sodium). 115) Inhibitoren der Chitinbiosynthese, Typ 0, wie beispielsweise Benzoylharnstoffe, z.B. Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, 114) nicotinergic acetylcholine receptor antagonists, such as Bensultap, Cartap (hydrochloride), thiocyclam, and thiosultap (-sodium). 115) inhibitors of chitin biosynthesis, type 0, such as benzoylureas, eg bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron,
Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron und Triflumuron. Hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
116) Inhibitoren der Chitinbiosynthese, Typ 1 , wie beispielsweise Buprofezin. 116) inhibitors of chitin biosynthesis, type 1, such as buprofezin.
117) Häutungsstörende Wirkstoffe, wie beispielsweise Cyromazine. 118) Ecdysonagonisten/-disruptoren, wie beispielsweise Diacylhydrazine, z.B. 117) Moisture-disrupting agents, such as cyromazines. 118) ecdysone agonists / disruptors such as diacylhydrazines, e.g.
Chromafenozide, Halofenozide, Methoxyfenozide und Tebufenozide. Chromafenozide, Halofenozide, Methoxyfenozide and Tebufenozide.
119) Oktopaminerge Agonisten, wie beispielsweise Amitraz. I20) Komplex-I l l-Elektronentransportinhibitoren, wie beispielsweise Hydramethylnon; Acequinocyl; Fluacrypyrim. 119) Octopaminergic agonists, such as amitraz. I20) complex I l electron transport inhibitors such as, for example, hydramethylnone; acequinocyl; Fluacrypyrim.
121 ) Komplex-I-Elektronentransportinhibitoren, beispielsweise aus der Gruppe der METI-Akarizide, z.B. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufen- pyrad, Tolfenpyrad; oder Rotenone (Derris). 121) Complex I electron transport inhibitors, for example from the group of the METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad; or Rotenone (Derris).
122) Spannungsabhängige Natriumkanal-Blocker, z.B. Indoxacarb; Metaflumizone. 122) voltage dependent sodium channel blockers, e.g. indoxacarb; Metaflumizone.
123) Inhibitoren der Acetyl-CoA-Carboxylase, wie beispielsweise Tetronsäure-Derivate, z.B. Spirodiclofen und Spiromesifen; oder Tetramsäure-Derivate, z.B. Spirotetramat. 123) inhibitors of acetyl-CoA carboxylase, such as tetronic acid derivatives, e.g. Spirodiclofen and spiromesifen; or tetramic acid derivatives, e.g. Spirotetramat.
124) Komplex-IV-Elektronentransportinhibitoren, wie beispielsweise Phosphine, z.B. Aluminiumphosphid, Kalziumphosphid, Phosphin, Zinkphosphid; oder Cyanid. I25) Komplex-I l-Elektronentransportinhibitoren, wie beispielsweise Cyenopyrafen. 124) complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine, zinc phosphide; or cyanide. I25) Complex I l electron transport inhibitors, such as cyenopyrafen.
I26) Ryanodinrezeptor-Effektoren, wie beispielsweise Diamide, z.B. Flubendiamide, Chiorantraniiiprole (Rynaxypyr), Cyantraniliproie (Cyazypyr) sowie 3-Brom-N-{2-brom- 4-chlor-6-[(1 -cyclopropylethyl)carbamoyl]phenyl}-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-5- carboxamid (bekannt aus WO2005/077934) oder Methyl-2-[3,5-dibrom-2-({[3-brom-1 - (3-chlorpyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1 ,2- dimethylhydrazincarboxy-iat (bekannt aus WO2007/043677). Weitere Wirkstoffe mit unbekanntem Wirkmechanismus, wie beispielsweise I26) ryanodine receptor effectors, such as, for example, diamides, eg flubendiamide, chiorantraniipyrole (rynaxypyr), cyantraniliproie (cyazypyr) and 3-bromo-N- {2-bromo-4-chloro-6 - [(1-cyclopropylethyl) carbamoyl] phenyl} -1 - (3-chloropyridin-2-yl) -1H-pyrazole-5- carboxamide (known from WO2005 / 077934) or methyl 2- [3,5-dibromo-2 - ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) benzoyl] -1, 2-dimethylhydrazinecarboxylate (known from WO2007 / 043677). Other drugs with unknown mechanism of action, such as
Azadirachtin, Amidoflumet, Benzoximate, Bifenazate, Chinomethionat, Cryolite, Cyflumetofen, Dicofol, 5-chloro-2-[(3,4,4-trifluorobut-3-en-1 -yl)sulfonyl]-1 ,3-thiazol, Flu- fenerim, Pyridalyl und Pyrifluquinazon; desweiteren Präparate auf Basis von Bacillus firmus (1-1582, BioNeem, Votivo) sowie folgende bekannte wirksame Verbindungen 4- {[(6-Brompyrid-3-yl)methyl](2-fluorethyl)amino}furan-2(5H)-on (bekannt aus WO Azadirachtin, amidoflumet, benzoximate, bifenazate, quinomethionate, cryolite, cyflumetofen, dicofol, 5-chloro-2 - [(3,4,4-trifluorobut-3-en-1-yl) sulfonyl] -1, 3-thiazole, Flu - fenerim, pyralidyl and pyrifluquinazone; furthermore preparations based on Bacillus firmus (1-1582, BioNeem, Votivo) and the following known active compounds 4- {[(6-bromopyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) - on (known from WO
2007/1 15644), 4-{[(6-Fluorpyrid-3-yl)methyl](2,2-difluorethyl)amino}furan-2(5H)-on (bekannt aus WO 2007/1 15644), 4-{[(2-Chlor-1 ,3-thiazol-5-yl)methyl](2- fluorethyl)amino}furan-2(5H)-on (bekannt aus WO 2007/115644), 4-{[(6-Chlorpyrid-3- yl)methyl](2-fluorethyl)amino}furan-2(5H)-on (bekannt aus WO 2007/115644), 4-{[(6- Chlorpyrid-3-yl)methyl](2,2-difluorethyl)amino}furan-2(5H)-on (bekannt aus WO 2007/1 15644), 4 - {[(6-fluoropyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one (known from WO 2007/1 15644), 4- {[(2-chloro-1,3-thiazol-5-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (known from WO 2007/115644), 4 - {[(6- Chloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (known from WO 2007/115644), 4 - {[(6-chloropyrid-3-yl) methyl] (2, 2-difluoroethyl) amino} furan-2 (5H) -one (known from WO
2007/1 15644), 4-{[(6-Chlor-5-fluorpyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on (bekannt aus WO 2007/1 15643), 4-{[(5,6-Dichlorpyrid-3-yl)methyl](2- fluorethyl)amino}furan-2(5H)-on (bekannt aus WO 2007/1 15646), 4-{[(6-Chlor-5- fluorpyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on (bekannt aus WO 2007/1 15644), 4 - {[(6-chloro-5-fluoropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one (known from WO 2007/1 15643), 4- {[(5,6-dichloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (known from WO 2007/1 15646), 4 - {[(6-chloro-5 - fluoropyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one (known from WO
2007/1 15643), 4-{[(6-Chlorpyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on 2007/1 15643), 4 - {[(6-chloropyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one
(bekannt aus EP0539588), 4-{[(6-Chlorpyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on (bekannt aus EP0539588), [1 -(6-Chlorpyridin-3-yl)ethyl](methyl)oxido-A4- sulfanylidencyanamid (bekannt aus WO 2007/149134) und seine Diastereomere {[(1 R)-1 -(6-Chlorpyridin-3-yl)ethyl](methyl)oxido- .(,-sulfanyliden}cyanamid und {[(1 S)-1- (6-Chlorpyridin-3-yl)ethyl](methyl)oxido- .6-sulfanyliden}cyanamid (ebenfalls bekannt aus WO 2007/149134) sowie Sulfoxaflor (ebenfalls bekannt aus WO 2007/149134), 1 - [2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H (known from EP0539588), 4 - {[(6-chloropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one (known from EP0539588), [1- (6-chloropyridine-3-) yl) ethyl] (methyl) oxido-A 4 -sulfanylidenecyanoanamide (known from WO 2007/149134) and its diastereomers {[(1R) -1- (6-chloropyridin-3-yl) ethyl] (methyl) oxido. ( -sulfanylidene) cyanamide and {[(1S) -1- (6-chloropyridin-3-yl) ethyl] (methyl) oxido- 6- sulfanylidene} cyanamide (also known from WO 2007/149134) and sulfoxaflor ( also known from WO 2007/149134), 1 - [2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl] -3- (trifluoromethyl) -1H
Triazol-5-amine (bekannt aus WO 2006/043635), [(3S,4aR, 12R, 12aS, 12ßS)-3- [(Cyclopropylcarbonyl)oxy]-6, 12-dihydroxy-4, 12b-dimethyl-1 1 -oxo-9-(pyridin-3-yl)- 1 ,3,4,4a, 5,6,6a, 12, 12a, 12ß-decahydro-2H, 1 1 H-benzo[f]pyrano[4,3-b]chromen-4- yl]methylcyclopropancarboxylat (bekannt aus WO 2006/129714), 2-Cyano-3- (difluormethoxy)-N,N-dimethylbenzolsulfonamid (bekannt aus WO2006/056433), 2- Cyano-3-(difluormethoxy)-N-methylbenzolsulfonamid (bekannt aus WO2006/100288), 2-Cyano-3-(difluormethoxy)-N-ethylbenzolsulfonamid (bekannt aus WO2005/035486), 4-(Difluormethoxy)-N-ethyl-N-methyl-1 ,2-benzothiazol-3-amin-1 , 1 -dioxid (bekannt aus WO2007/057407), N-[1 -(2,3-Dimethylphenyl)-2-(3,5-dimethylphenyl)ethyl]-4,5-dihydro- 1 ,3-thiazol-2-amin (bekannt aus WO2008/ 04503), {1 '-[(2E)-3-(4-Chlorphenyl)prop-2- en-1 -yl]-5-fluorspiro[indol-3,4'-piperidin]-1 (2H)-yl}(2-chlorpyridin-4-yl)methanon Triazole-5-amines (known from WO 2006/043635), [(3S, 4aR, 12R, 12aS, 12βS) -3- [(cyclopropylcarbonyl) oxy] -6,12-dihydroxy-4,12b-dimethyl-11 -oxo-9- (pyridin-3-yl) -1,4,4,4a, 5,6,6a, 12,12a, 12β-decahydro-2H, 1: 1 H-benzo [f] pyrano [4,3 -b] chromen-4-yl] methylcyclopropanecarboxylate (known from WO 2006/129714), 2-cyano-3- (difluoromethoxy) -N, N-dimethylbenzenesulfonamide (known from WO2006 / 056433), 2-cyano-3- (difluoromethoxy ) -N-methylbenzenesulfonamide (known from WO2006 / 100288), 2-cyano-3- (difluoromethoxy) -N-ethylbenzenesulfonamide (known from WO2005 / 035486), 4- (difluoromethoxy) -N-ethyl-N-methyl-1,2-benzothiazol-3-amine-1,1-dioxide (known from WO2007 / 057407), N- [1- (2,3-dimethylphenyl) -2- (3,5-dimethylphenyl) ethyl] -4,5-dihydro-1,3-thiazol-2-amine (known from WO2008 / 04503), {1 '- [(2E) -3- (4-chlorophenyl) -prop-2-en-1-yl] -5-fluorospiro [indole-3,4'-piperidin] -1 (2H ) -yl} (2-chloropyridin-4-yl) methanone
(bekannt aus WO2003106457), 3-(2,5-Dimethylphenyl)-4-hydroxy-8-methoxy-1 ,8- diazaspiro[4.5]dec-3-en-2-on (bekannt aus WO2009049851 ), 3-(2,5-Dimethylphenyl)- 8-methoxy-2-oxo-1 ,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonat (bekannt aus (known from WO2003106457), 3- (2,5-dimethylphenyl) -4-hydroxy-8-methoxy-1,8-diazaspiro [4.5] dec-3-en-2-one (known from WO2009049851), 3- ( 2,5-dimethylphenyl) - 8-methoxy-2-oxo-1,8-diazaspiro [4.5] dec-3-en-4-yl-ethyl carbonate (known from
WO2009049851 ), 4-(But-2-in-1 -yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluorpyrimidin (bekannt aus WO2004099160), (2, 2,3,3,4,4, 5,5-Octafluorpentyl)(3,3,3- trifluorpropyl)malononitril (bekannt aus WO2005063094), (2,2,3,3,4,4,5,5- Octafluorpentyl)(3,3,4,4,4-pentafluorbutyl)malononitril (bekannt aus WO2005063094), 8-[2-(Cyclopropylmethoxy)-4-(trifluormethyl)phenoxy]-3-[6-(trifluormethyl)pyridazin-3- yl]-3-azabicyclo[3.2.1]octan (bekannt aus WO2007040280 / 282), 2-Ethyl-7-methoxy-3- methyl-6-[(2,2,3,3-tetrafluor-2,3-dihydro-1 ,4-benzodioxin-6-yl)oxy]chinolin-4-yl- methylcarbonat (bekannt aus JP20081 10953), 2-Ethyl-7-methoxy-3-methyl-6-[(2, 2,3,3- tetrafluor-2,3-dihydro-1 ,4-benzodioxin-6-yl)oxy]chinolin-4-ylacetat (bekannt aus WO2009049851), 4- (but-2-yn-1-ylxy) -6- (3,5-dimethylpiperidin-1-yl) -5-fluoropyrimidine (known from WO2004099160), (2, 2,3,3,4 , 4,5,5-octafluoropentyl) (3,3,3-trifluoropropyl) malononitrile (known from WO2005063094), (2,2,3,3,4,4,5,5-octafluoropentyl) (3,3,4 , 4,4-pentafluorobutyl) malononitrile (known from WO2005063094), 8- [2- (cyclopropylmethoxy) -4- (trifluoromethyl) phenoxy] -3- [6- (trifluoromethyl) pyridazin-3-yl] -3-azabicyclo [ 3.2.1] octane (known from WO2007040280 / 282), 2-ethyl-7-methoxy-3-methyl-6 - [(2,2,3,3-tetrafluoro-2,3-dihydro-1, 4-benzodioxin -6-yl) oxy] quinolin-4-ylmethyl carbonate (known from JP20081 10953), 2-ethyl-7-methoxy-3-methyl-6 - [(2,3,3,3-tetrafluoro-2,3 -dihydro-1,4-benzodioxin-6-yl) oxy] quinolin-4-ylacetate (known from
JP2008110953), PF1364 (Chemical Abstracts Nr 1204776-60-2, bekannt aus JP2008110953), PF1364 (Chemical Abstracts No. 1204776-60-2, known from
JP2010018586), 5-[5-(3,5-Dichlorphenyl)-5-(trifluormethyl)-4,5-dihydro-1 ,2-oxazol-3- yl]-2-(1 H-1 ,2,4-triazol-1 -yl)benzonitril (bekannt aus WO2007075459), 5-[5-(2-JP2010018586), 5- [5- (3,5-dichlorophenyl) -5- (trifluoromethyl) -4,5-dihydro-1,2-oxazol-3-yl] -2- (1H-1, 2.4 -triazol-1-yl) benzonitrile (known from WO2007075459), 5- [5- (2-
Chlorpyridin-4-yl)-5-(trifluormethyl)-4,5-dihydro-1 ,2-oxazol-3-yl]-2-(1 H-1 ,2,4-triazo!-1 - y!)benzonitril (bekannt aus WO2007075459), 4-[5-(3,5-Dichlorphenyl)-5- (trifluormethyl)-4,5-dihydro-1 ,2-oxazol-3-yl]-2-methyl-N-{2-oxo-2-[(2,2,2- trifluorethyl)amino]ethyl}benzamid (bekannt aus WO2005085216). Chloropyridin-4-yl) -5- (trifluoromethyl) -4,5-dihydro-1,2-oxazol-3-yl] -2- (1H-1, 2,4-triazo! -1-y!) benzonitrile (known from WO2007075459), 4- [5- (3,5-dichlorophenyl) -5- (trifluoromethyl) -4,5-dihydro-1,2-oxazol-3-yl] -2-methyl-N- { 2-oxo-2 - [(2,2,2-trifluoroethyl) amino] ethyl} benzamide (known from WO2005085216).
Safener sind vorzugsweise ausgewählt aus der Gruppe bestehend aus: Safeners are preferably selected from the group consisting of:
Verbindungen der Formel (S1 ), wobei die Symbole und Indizes folgende Bedeutungen haben: riA ist eine natürliche Zahl von 0 bis 5, vorzugsweise 0 bis 3; Compounds of the formula (S1), where the symbols and indices have the following meanings: riA is a natural number of 0 to 5, preferably 0 to 3;
RA1 ist Halogen, (d-C4)Alkyl, (Ci-C4)Alkoxy, Nitro oder (Ci-C4)Haloalkyl; RA 1 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, nitro or (C 1 -C 4 ) haloalkyl;
WA ist ein unsubstituierter oder substituierter divalenter heterocyclischer Rest aus der Gruppe der teilungesättigten oder aromatischen Fünfring-Heterocyclen mit 1 bis 3 Heteroringatomen aus der Gruppe N und O, wobei mindestens ein N-Atom und höchstens ein O-Atom im Ring enthalten ist, vorzugsweise ein Rest aus der Gruppe (WA 1) bis (WA4), WA is an unsubstituted or substituted divalent heterocyclic radical selected from the group consisting of the monounsaturated or aromatic five-membered heterocycles having 1 to 3 hetero ring atoms from the group N and O, where at least one N atom and at most one O atom are present in the ring, preferably one Remainder of the group (W A 1 ) to (WA 4 ),
rriA ist 0 oder 1 ; rriA is 0 or 1;
RA2 ist ORA3, SRA3 oder NRA3RA4 oder ein gesättigter oder ungesättigter 3- bis 7- gliedriger Heterocyclus mit mindestens einem N-Atom und bis zu 3 Heteroatomen, vorzugsweise aus der Gruppe O und S, der über das N-Atom mit der Carbonylgruppe in (S1 ) verbunden ist und unsubstituiert oder durch Reste aus der Gruppe (Ci-C4)Alkyl, (Ci-C4)Alkoxy oder gegebenenfalls substituiertes Phenyl substituiert ist, vorzugsweise ein Rest der Formel ORA3, NHRA4 oder N(CH3)2, insbesondere der Formel ORA3; RA 2 is ORA 3 , SRA 3 or NRA 3 RA 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is bonded via the N- Atom is connected to the carbonyl group in (S1) and is unsubstituted or substituted by radicals from the group (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy or optionally substituted phenyl, preferably a radical of the formula ORA 3 , NHRA 4 or N (CH 3) 2, in particular of the formula ORA 3 ;
RA3 ist Wasserstoff oder ein unsubstituierter oder substituierter aliphatischer RA 3 is hydrogen or an unsubstituted or substituted aliphatic
Kohlen wasserstoffrest, vorzugsweise mit insgesamt 1 bis 18 C-Atomen; Carbon hydrogen radical, preferably having a total of 1 to 18 carbon atoms;
RA4 ist Wasserstoff, (Ci-Ce)Alkyl, (Ci-Ce)Alkoxy oder substituiertes oder RA 4 is hydrogen, (Ci-Ce) alkyl, (Ci-Ce) alkoxy or substituted or
unsubstituiertes Phenyl; unsubstituted phenyl;
RA5 ist H, (Ci-C8)Alkyl, (CrC8)Haloalkyl, (Ci-C4)Alkoxy(Ci-C8)Alkyl, Cyano oder COORA9, worin RA 9 Wasserstoff, (Ci-C8)Alkyl, (Ci-C8)Haloalkyl, (Ci-C4)Alkoxy- (Ci-C4)alkyl, (Ci-Ce)Hydroxyalkyl, (C3-Ci2)Cycloalkyl oder Tri-(Ci-C4)-alkyl-silyl ist; RA6, RA7, RA8 sind gleich oder verschieden Wasserstoff, (Ci-C8)Alkyl, (Ci-C8)Haloalkyl,RA 5 is H, (C 1 -C 8 ) alkyl, (C 1 -C 8 ) haloalkyl, (C 1 -C 4 ) alkoxy (C 1 -C 8 ) alkyl, cyano or COORA 9 , in which R A 9 is hydrogen, (C 1 -C 8 ) alkyl, (Ci-C 8) haloalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-Ce) hydroxyalkyl, (C3-Ci2) -cycloalkyl or tri- (Ci-C 4 ) -alkyl-silyl; RA 6 , RA 7 , RA 8 are identical or different hydrogen, (C 1 -C 8 ) alkyl, (C 1 -C 8 ) haloalkyl,
(C3-(C 3 -
Ci2)Cycloalkyl oder substituiertes oder unsubstituiertes Phenyl; vorzugsweise: a) Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure (S1a), vorzugsweise Verbindungen wie 1-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl- 2- pyrazolin-3-carbonsäure, 1-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2- pyrazoiin-3-carbonsäureethylester (S1 -1 ) ("Mefenpyr-diethyl"), und verwandte Verbin- düngen, wie sie in der WO-A-91/07874 beschrieben sind; Ci2) cycloalkyl or substituted or unsubstituted phenyl; preferably: a) compounds of the type of dichlorophenylpyrazoline-3-carboxylic acid (S1 a ), preferably compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid, 1- ( 2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoiin-3-carboxylic acid ethyl ester (S1 -1) ("mefenpyr-diethyl"), and related compounds, as described in WO-A -91 / 07874 are described;
b) Derivate der Dichlorphenylpyrazoicarbonsäure (S1 b), vorzugsweise Verbindungen wie 1 -(2,4-Dichlorphenyl)-5-methyl-pyrazol-3-carbonsäureethylester (S1 -2), 1 -(2,4-Di-chlorphenyl)-5-isopropyl-pyrazol-3-carbonsäureethylester (S1 -3), b) derivatives of Dichlorphenylpyrazoicarbonsäure (S1 b), preferably compounds such as 1 - (2,4-dichlorophenyl) -5-methyl-pyrazole-3-carboxylate (S1 -2), 1 - (2,4-dichlorophenyl) - Ethyl 5-isopropyl-pyrazole-3-carboxylate (S1-3),
1 -(2,4-Dichlor-phenyl)-5-(1 , 1 -dimethyl-ethyl)pyrazol-3-carbonsäureethyi-ester (S1 -4) und verwandte Verbindungen, wie sie in EP-A-333 131 und EP-A-269 806  1- (2,4-dichloro-phenyl) -5- (1, 1-dimethyl-ethyl) -pyrazole-3-carboxylic acid ethyl ester (S1 -4) and related compounds as described in EP-A-333,131 and EP -A-269 806
beschrieben sind; are described;
c) Derivate der 1 ,5-Diphenyipyrazoi-3-carbonsäure (S1C), vorzugsweise Verbindungen wie 1 -(2,4-Dichlorphenyl)-5-phenylpyrazol-3-carbonsäureethy!ester (S1 -5), 1 -(2-Chlorphenyi)-5-phenylpyrazol-3-carbonsäuremethylester (S1 -6) und verwandte Verbindungen wie sie beispielsweise in der EP-A-268554 beschrieben sind; c) derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1 C ), preferably compounds such as 1- (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylic acid ethyl ester (S1 -5), 1- (2 -Chlorphenyi) -5-phenylpyrazole-3-carboxylic acid methyl ester (S1 -6) and related compounds as described for example in EP-A-268554;
d) Verbindungen vom Typ der Triazolcarbonsäuren (S1d), vorzugsweise d) compounds of the type of the triazolecarboxylic acids (S1 d ), preferably
Verbindungen wie Fenchlorazol(-ethylester), d.h. Compounds such as fenchlorazole (ethyl ester), i.
1 -(2,4-Dichlorphenyl)-5-trichlormethyi-(1 H)-1 ,2,4-triazol-3-carbonsäureethy!ester (S1 -7), und verwandte Verbindungen wie sie in EP-A-174 562 und EP-A-346 620 beschrieben sind;  1- (2,4-dichlorophenyl) -5-trichloromethyl (1 H) -1, 2,4-triazole-3-carboxylic acid ethyl ester (S1 -7), and related compounds as described in EP-A-174 562 and EP-A-346 620;
e) Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3- carbonsäure oder der 5,5-Diphenyl-2-isoxazo!in-3-carbonsäure (S1e), vorzugsweise Verbindungen wie 5-(2,4-Dichlorbenzyl)-2-isoxazolin-3-carbonsäureethyiester (S1 -8) oder 5-Phenyl-2-isoxazolin-3-carbonsäureethylester (S1 -9) und verwandte Verbindungen, wie sie in WO-A-91/08202 beschrieben sind, bzw. 5,5-Diphenyl-2-isoxazolin-3- carbonsäure (S1 -10) oder 5,5-Diphenyi-2-isoxazolin-3-carbonsäureethylester (S1 -1 1 ) ("Isoxadifen-ethyl") oder -n-propyiester (S1-12) oder der 5-(4-Fluorphenyl)-5-phenyi-2- isoxazolin-3-carbonsäureethylester (S1 -13), wie sie in der Patentanmeldung e) Compounds of the 5-benzyl- or carboxylic acid-5-phenyl-2-isoxazoline-3 or the 5,5-diphenyl-2-isoxazo! in-3-carboxylic acid (S1 e), preferably compounds such as 5- ( 2,4-Dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester (S1 -8) or 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-3-carboxylic acid (S1 -10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-1 1) ("isoxadifen-ethyl") or -n-propyiester (S1-12) or 5- (4-fluorophenyl) -5-phenyi-2-isoxazoline-3-carboxylic acid ethyl ester (S1 -13), as described in the patent application
WO-A-95/07897 beschrieben sind. WO-A-95/07897 are described.
S2) Chinolinderivate der Formel (S2), S2) quinoline derivatives of the formula (S2)
wobei die Symbole und Indizes folgende Bedeutungen haben: where the symbols and indices have the following meanings:
RB1 ist Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, Nitro oder (Ci-C4)Haloalkyl; RB 1 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, nitro or (C 1 -C 4 ) haloalkyl;
ne ist eine natürliche Zahl von 0 bis 5, vorzugsweise 0 bis 3; ne is a natural number of 0 to 5, preferably 0 to 3;
RB2 ist ORB 3, SRB3 oder NRB 3RB4 oder ein gesättigter RB 2 is OR B 3 , SRB 3 or NR B 3 RB 4 or a saturated one
oder ungesättigter 3- bis 7-gliedriger Heterocyclus mit mindestens einem N-Atom und bis zu 3 Heteroatomen, vorzugsweise aus der Gruppe O und S, der über das N-Atom mit der Carbonyigruppe in (S2) verbunden ist und unsubstituiert oder durch Reste aus der Gruppe (Ci-C4)Alkyl, (d-C4)Alkoxy oder gegebenenfalls substituiertes Phenyl substituiert ist, vorzugsweise ein Rest der Formel ORB3, NHRB4 oder N(CH3)2, insbesondere der Formel ORB3; or unsaturated 3- to 7-membered heterocycle having at least one N-atom and up to 3 heteroatoms, preferably from the group O and S, which is connected via the N-atom with the Carbonyigruppe in (S2) and unsubstituted or by radicals the group (Ci-C 4 ) alkyl, (dC 4 ) alkoxy or optionally substituted phenyl is substituted, preferably a radical of the formula ORB 3 , NHRB 4 or N (CH 3) 2, in particular the formula ORB 3 ;
RB3 ist Wasserstoff oder ein unsubstituierter oder substituierter aliphatischer Kohlenwasserstoffrest, vorzugsweise mit insgesamt 1 bis 8 C-Atomen; RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 8 C atoms;
RB4 ist Wasserstoff, (Ci-Ce)Alkyl, (Ci-Ce)Alkoxy oder substituiertes oder RB 4 is hydrogen, (Ci-Ce) alkyl, (Ci-Ce) alkoxy or substituted or
unsubstituiertes Phenyl; unsubstituted phenyl;
TB ist eine (Ci oder C2)-Alkandiylkette, die unsubstituiert oder mit einem oder zwei (Ci-C )Alkylresten oder mit [(d-C3)-Alkoxy]-carbonyl substituiert ist; vorzugsweise:  TB is a (Ci or C2) alkanediyl chain which is unsubstituted or substituted by one or two (Ci-C) alkyl radicals or by [(d-C3) alkoxy] carbonyl; preferably:
a) Verbindungen vom Typ der 8-Chinolinoxyessigsäure (S2a), vorzugsweise (5-Chlor-8-chinolinoxy)essigsäure-(1 -methylhexyl)ester ("Cloquintocet-mexyl") (S2-1 ), (5-Chlor-8-chinolinoxy)essigsäure-(1 ,3-dimethyl-but-1-yl)ester (S2-2), a) Compounds of the 8-quinolinoxyacetic acid (S2 a), preferably (5-chloro-8-quinolinoxy) acetic acid (1 -methylhexyl) ester ( "cloquintocet-mexyl") (S2-1), (5-chloro- 8-quinolinoxy) acetic acid (1, 3-dimethylbut-1-yl) ester (S2-2),
(5-Chlor-8-chinolinoxy)essigsäure-4-allyloxy-butylester (S2-3), (5-Chlor-8-chinolin- oxy)essigsäure-1-allyloxy-prop-2-ylester (S2-4), (5-Chlor-8-chinolinoxy)essigsäure- ethylester (S2-5), (5-Chlor-8-chinolinoxy)essigsäuremethylester (S2-6), (5-Chlor-8- chinolinoxy)essigsäureallylester (S2-7), (5-Chlor-8-chinolinoxy)essigsäure-2-(2- propyliden-iminoxy)-1 -ethylester (S2-8), (5-Chlor-8-chinolinoxy)essigsäure-2-oxo-prop- 1 -ylester (S2-9) und verwandte Verbindungen, wie sie in EP-A-86 750, EP-A-94 349 und EP-A-191 736 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) acetic acid 4-allyloxy-butyl ester (S2-3), (5-chloro-8-quinoline-oxy) acetic acid 1-allyloxy-prop-2-yl ester (S2-4), (5-chloro-8-quinolinoxy) acetic acid ethyl ester (S2-5), (5-chloro-8-quinolinoxy) acetic acid methyl ester (S2-6), (5-chloro-8-quinolinoxy) allyl acetate (S2-7), (5-Chloro-8-quinolinoxy) acetic acid 2- (2-propylidene-iminoxy) -1-ethyl ester (S2-8), (5-chloro-8-quinolinoxy) -acetic acid 2-oxo-prop-1-yl-ester (S2-9) and related compounds as described in EP-A-86,750, EP-A-94,349 and EP-A-191,736 or EP-A-0 492 366, as well as (5-chloro-8 - quinolinoxy) acetic acid (S2-10), their hydrates and salts, for example their lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, as they are in WO-A-2002/34048;
b) Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)malonsäure (S2b), b) compounds of the (5-chloro-8-quinolinoxy) malonic acid type (S2 b ),
vorzugsweise Verbindungen wie (5-Chlor-8-chinolinoxy)malonsäurediethylester, (5-Chlor- 8-chinolinoxy)malonsäurediallylester, preferably compounds such as diethyl (5-chloro-8-quinolinoxy) malonate, (5-chloro-8-quinolinoxy) malonic acid diallyl ester,
(5-Chlor-8-chinolinoxy)malonsäure-methyl-ethylester und verwandte Verbindungen, wie sie in EP-A-0 582 198 beschrieben sind.  (5-chloro-8-quinolinoxy) malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198.
S3) Verbindungen der Formel (S3) S3) compounds of the formula (S3)
wobei die Symbole und Indizes folgende Bedeutungen haben: Rc1 ist (Ci-C4)Alkyl, (Ci-C4)Haloalkyl, (C2-C4)Alkenyl, (C2-C4)Haloalkenyl, where the symbols and indices have the following meanings: Rc 1 is (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl,
(C3-C )Cycloalkyl, vorzugsweise Dichlormethyl; (C3-C) cycloalkyl, preferably dichloromethyl;
Rc2, Rc3 sind gleich oder verschieden Wasserstoff, (Ci-C4)Alkyl, (C2-C4)Alkenyl, (C2-C )Alkinyl, (Ci-C4)Haloalkyl, (C2-C4)Haloalkenyl, (Ci-C4)Alkylcarbamoyl- (Ci-C )alkyl, (C2-C4)Alkenylcarbamoyl-(Ci-C )alkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, Dioxolanyl-(Ci-C )alkyl, Thiazolyl, Furyl, Furylalkyl, Thienyl, Piperidyl, substituiertes oder unsubstituiertes Phenyl, oder Rc2 und Rc3 bilden zusammen einen substituierten oder unsubstituierten heterocyclischen Ring, vorzugsweise einen Oxazolidin-, Rc 2, rc 3 are identical or different hydrogen, (Ci-C 4) alkyl, (C2-C4) alkenyl, (C 2 -C) alkynyl, (Ci-C 4) haloalkyl, (C 2 -C 4) haloalkenyl, (Ci-C 4) alkylcarbamoyl (Ci-C) alkyl, (C 2 -C 4) Alkenylcarbamoyl- (Ci-C) alkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, dioxolanyl (Ci-C) alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc 2 and Rc 3 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine,
Thiazolidin-, Piperidin-, Morpholin-, Hexahydropyrimidin- oder Benzoxazinring; Thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring;
vorzugsweise: Wirkstoffe vom Typ der Dichloracetamide, die häufig als preferably: active substances of the dichloroacetamide type, often as
Vorauflaufsafener (bodenwirksame Safener) angewendet werden, wie z. B. Pre-emergence safeners (soil-active safeners) are applied, such. B.
"Dichlormid" (N,N-Diallyl-2,2-dichloracetamid) (S3-1 ), "R-29148" (3-Dichloracetyl-2,2,5- trimethyl-1 ,3-oxazolidin) der Firma Stauffer (S3-2), "R-28725" (3-Dichloracetyl-2,2,- dimethyl-1 ,3-oxazolidin) der Firma Stauffer (S3-3), "Benoxacor" (4-Dichloracetyl-3,4- dihydro-3-methyl-2H-1 ,4-benzoxazin) (S3-4), "PPG-1292" (N-Allyl-N-[(1 ,3-dioxolan-2- yl)-methyl]-dichloracetamid) der Firma PPG Industries (S3-5), "DKA-24" (N-Allyl-N- [(allylaminocarbonyl)methy!]-dichloracetamid) der Firma Sagro-Chem (S3-6), "AD-67" oder "MON 4660" (3-Dichloracetyl-1-oxa-3-aza-spiro[4,5]decan) der Firma Nitrokemia bzw. Monsanto (S3-7), "TI-35" (1 -Dichloracetyl-azepan) der Firma TRI-Chemical RT (S3-8), "Dicionon" (Dicyclonon) oder "BAS145138" oder "LAB145138" (S3-9) ((RS)-1 - Dichloracetyl-3,3,8a-trimethylperhydropyrrolo[1 ,2-a]pyrimidin-6-on) der Firma BASF, "Furiiazol" oder "MON 13900" ((RS)-3-Dichloracetyl-5-(2-furyi)-2,2-dimethyloxazolidin) (S3-10); sowie dessen (R)-Isomer (S3-1 1 ). "Dichloromid" (N, N-diallyl-2,2-dichloroacetamide) (S3-1), "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-dichloroacetyl-3,4-dihydro 3-methyl-2H-1,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N - [(1, 3-dioxolan-2-yl) -methyl] -dichloroacetamide) of PPG Industries (S3-5), "DKA-24" (N-allyl-N- [(allylaminocarbonyl) methyl] - dichloroacetamide) from Sagro-Chem (S3-6), "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane) from Nitrokemia or Monsanto (S3-7), "TI-35" (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8), "dicionone" (dicyclonone) or "BAS145138" or " LAB145138 "(S3-9) ((RS) -1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo [1,2-a] pyrimidin-6-one) from BASF," Furiiazol "or" MON 13900 "(( RS) -3-dichloroacetyl-5- (2-furyi) -2,2-dimethyloxazolidine) (S3-10); and its (R) isomer (S3-1 1).
S4) N-Acylsuifonamide der Formel (S4) und ihre Salze, S4) N-acylsulfonamides of the formula (S4) and their salts,
worin die Symbole und Indizes folgende Bedeutungen haben: XD ist CH oder N; wherein the symbols and indices have the following meanings: X D is CH or N;
RD1 ist CO-NRD 5RD6 oder NHCO-RD7; RD 1 is CO-NR D 5 RD 6 or NHCO-RD 7 ;
RD2 ist Halogen, (Ci-C4)Haloalkyl, (Ci-C4)Haloalkoxy, Nitro, (Ci-C4)Alkyl, RD 2 is halogen, (Ci-C 4) haloalkyl, (Ci-C 4) haloalkoxy, nitro, (Ci-C 4) alkyl,
(Ci-C4)Alkoxy, (Ci-C4)Alkylsulfonyl, (Ci-C4)Alkoxycarbonyl oder (Ci-C4)Alkylcarbonyl; RD3 ist Wasserstoff, (Ci-C4)Alkyl, (C2-C4)Alkenyl oder (C2-C4)Alkinyl; (Ci-C 4) alkoxy, (Ci-C 4) alkylsulfonyl, (Ci-C 4) alkoxycarbonyl or (Ci-C 4) alkylcarbonyl; RD 3 is hydrogen, (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkenyl or (C 2 -C 4 ) alkynyl;
RD 4 ist Halogen, Nitro, (d-C )Alkyl, (d-C4)Haloalkyl, (Ci-C4)Haloalkoxy, R D 4 is halogen, nitro, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy,
(C3-C6)Cycloalkyl, Phenyl, (Ci-C4)Alkoxy, Cyano, (Ci-C4)Alkylthio, (Ci-C4)Alkylsulfinyl, (Ci-C4)Alkylsulfonyl, (Ci-C4)Alkoxycarbonyl oder (Ci-C )Alkylcarbonyl; (C 3 -C 6) cycloalkyl, phenyl, (Ci-C 4) alkoxy, cyano, (Ci-C 4) alkylthio, (Ci-C 4) alkylsulfinyl, (Ci-C 4) alkylsulfonyl, (Ci-C 4 ) Alkoxycarbonyl or (Ci-C) alkylcarbonyl;
RD5 ist Wasserstoff, (Ci-C6)Alkyl, (C3-C6)Cycloalkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (Cs-CeJCycloalkenyl, Phenyl oder 3- bis 6-gliedriges Heterocyclyl enthaltend VD Heteroatome aus der Gruppe Stickstoff, Sauerstoff und Schwefel, wobei die sieben letztgenannten Reste durch VD Substituenten aus der Gruppe Halogen, (Ci-CeJAIkoxy, (Ci-C6)Haloalkoxy, (Ci-C2)Alkylsulfinyl, (Ci-C2)Alkylsulfonyl, (C3-C6)Cycloalkyl, (Ci- C4)Alkoxycarbonyl, (Ci-C4)Alkylcarbonyl und Phenyl und im Falle cyclischer Reste auch (Ci-C ) Alkyl und (Ci-C4)Haloalkyl substituiert sind; RD6 ist Wasserstoff, (Ci-C6)Alkyl, (C2-C6)Alkenyl oder (C2-C6)Alkinyl, wobei die drei letztgenannten Reste durch VD Reste aus der Gruppe Halogen, Hydroxy, (d-C4)Alkyl, (Ci-C4)Alkoxy und (Ci-C4)Alkylthio substituiert sind, oder RD 5 is hydrogen, (Ci-C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (Cs-CeJCycloalkenyl, phenyl or 3-6 heterocyclyl-containing hetero-hetero atoms from the group consisting of nitrogen, oxygen and sulfur, where the last seven radicals are represented by VD substituents from the group consisting of halogen, (C 1 -C 6 -alkoxy, (C 1 -C 6 ) -haloalkoxy, (C 1 -C 2 ) -alkylsulfinyl, ( Ci-C 2 ) alkylsulfonyl, (C 3 -C 6 ) cycloalkyl, (Ci- C 4 ) alkoxycarbonyl, (Ci-C 4 ) alkylcarbonyl and phenyl and in the case of cyclic radicals also (Ci-C) alkyl and (Ci-C 4 ) haloalkyl are substituted; RD 6 is hydrogen, (Ci-C 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, wherein the last three radicals mentioned by VD radicals selected from the group consisting of halogen, hydroxy, (d-C4 ) Alkyl, (C 1 -C 4 ) alkoxy and (C 1 -C 4 ) alkylthio, or
RD5 und RD6 gemeinsam mit dem dem sie tragenden Stickstoffatom einen Pyrrolidinyl- oder Piperidinyl-Rest bilden; RD 5 and RD 6 together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical;
RD7 ist Wasserstoff, (Ci-C4)Alkylamino, Di-(Ci-C4)alkylamino, (Ci-C6)Alkyl, RD 7 is hydrogen, (Ci-C 4) alkylamino, di (Ci-C 4) alkylamino, (Ci-C 6) alkyl,
(C3-C6)Cycloalkyl, wobei die 2 letztgenannten Reste durch VD Substituenten aus der Gruppe Halogen, (Ci-C4)Alkoxy, (d-C6)Haloalkoxy und (Ci-C4)Alkylthio und im Falle cyclischer Reste auch (Ci-C4)Alkyl und (Ci-C4)Haloalkyl substituiert sind; (C3-C6) cycloalkyl, where the 2 last-mentioned radicals by VD substituents selected from the group consisting of halogen, (Ci-C 4 ) alkoxy, (d-C6) haloalkoxy and (Ci-C 4 ) alkylthio and in the case of cyclic radicals also (Ci -C 4) alkyl and (Ci-C4) haloalkyl groups;
nD ist 0, 1 oder 2; n D is 0, 1 or 2;
rriD ist 1 oder 2; radius is 1 or 2;
VD ist 0, 1 , 2 oder 3; davon bevorzugt sind Verbindungen vom Typ der N-Acylsulfonamide, z.B. der nachfolgenden Formel (S4a), die z. B. bekannt sind aus WO-A-97/45016 VD is 0, 1, 2 or 3; Of these, preference is given to compounds of the N-acylsulfonamide type, for example of the following formula (S4 a ), which are, for example, B. are known from WO-A-97/45016
worin wherein
RD7 (Ci-C6)Alkyl, (C3-C-6)Cycloalkyl, wobei die 2 letztgenannten Reste durch VD Substituenten aus der Gruppe Halogen, (Ci-C4)Alkoxy, (Ci-Ce)Haloalkoxy und (d- C4)Alkylthio und im Falle cyclischer Reste auch (Ci-C4)Alkyl und (Ci-C4)Haloalkyl substituiert sind; RD 7 (Ci-C6) alkyl, (C3-C-6) cycloalkyl, wherein the latter two radicals by VD substituents selected from the group consisting of halogen, (Ci-C 4 ) alkoxy, (Ci-Ce) haloalkoxy and (d-C 4 ) alkylthio and in the case of cyclic radicals are also (Ci-C4) alkyl and (Ci-C 4 ) haloalkyl substituted;
RD4 Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, CF3; RD 4 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3;
ITID 1 oder 2; ITID 1 or 2;
VD ist 0, 1 , 2 oder 3 bedeutet; sowie Acylsulfamoylbenzoesäureamide, z.B. der nachfolgenden Formel (S4b), die z.B. bekannt sind aus WO-A-99/16744, z.B. solche worin VD is 0, 1, 2 or 3; and acylsulfamoylbenzamides, for example of the formula (S4 b), for example are known from WO-A-99/16744, eg those in which
RD5 = Cyclopropyl und (RD4) = 2-OMe ist ("Cyprosulfamide", S4-1 ), RD 5 = cyclopropyl and (RD 4 ) = 2-OMe ("Cyprosulfamide", S4-1),
RD5 = Cyclopropyl und (RD4) = 5-CI-2-OMe ist (S4-2), RD 5 = cyclopropyl and (RD 4 ) = 5-CI-2-OMe is (S4-2),
RD5 = Ethyl und (RD4) = 2-OMe ist (S4-3), RD 5 = ethyl and (RD 4 ) = 2-OMe is (S4-3),
RD5 = Isopropyl und (RD4) = 5-CI-2-OMe ist (S4-4) und RD 5 = isopropyl and (RD 4 ) = 5-CI-2-OMe is (S4-4) and
RD5 = Isopropyl und (RD4) = 2-OMe ist (S4-5). sowie Verbindungen vom Typ der N-Acylsulfamoylphenylharnstoffe der Formel (S4C), die z.B. bekannt sind aus der EP-A-365484, RD 5 = isopropyl and (RD 4 ) = 2-OMe is (S4-5). and also compounds of the type of the N-acylsulfamoylphenylureas of the formula (S 4 C ) which are known, for example, from EP-A-365484,
worin wherein
RD8 und RD9 unabhängig voneinander Wasserstoff, (Ci-Cs)Alkyl, (C3-C-8)Cycloalkyl,RD 8 and RD 9 independently of one another are hydrogen, (C 1 -C 5) alkyl, (C 3 -C 8) cycloalkyl,
(C3-C6)Alkenyl, (C3-C6)Alkinyl, (C 3 -C 6 ) alkenyl, (C 3 -C 6 ) alkynyl,
RD4 Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, CF3 RD 4 halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3
niD 1 oder 2 bedeutet; beispielsweise niD is 1 or 2; for example
1 -[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3-methylharnstoff,  1 - [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
1 -[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylharnstoff,  1 - [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea,
1 -[4-(N-4,5-Dimethylbenzoylsulfamoyl)phenyl]-3-methylharnstoff.  1 - [4- (N-4,5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea.
S5) Wirkstoffe aus der Klasse der Hydroxyaromaten und der aromatisch- aliphatischen Carbonsäurederivate (S5), z.B. 3,4,5-Triacetoxybenzoesäureethylester, 3,5-Di-methoxy-4-hydroxybenzoesäure, 3,5-Dihydroxybenzoesäure, 4- Hydroxysalicylsäure, 4-Fluorsalicyclsäure, 2-Hydroxyzimtsäure, 2,4-Dichlorzimtsäure, wie sie in der WO-A-2004/08463 , WO-A-2005/0 5994, WO-A-2005/0 6001 beschrieben sind. S5) Active substances from the class of the hydroxyaromatics and the aromatic-aliphatic carboxylic acid derivatives (S5), for example ethyl 3,4,5-triacetoxybenzoate, 3,5-di-methoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4 -Fluorsalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/08463, WO-A-2005/0 5994, WO-A-2005/0 6001.
S6) Wirkstoffe aus der Klasse der 1 ,2-Dihydrochinoxalin-2-one (S6), z.B. S6) active compounds from the class of 1, 2-dihydroquinoxaline-2-ones (S6), e.g.
1 -Methyl-3-(2-thienyl)-1 ,2-dihydrochinoxalin-2-on, 1 -Methyl-3-(2-thienyl)-1 ,2-dihydro- chinoxalin-2-thion, 1 -(2-Aminoethyl)-3-(2-thienyl)-1 ,2-dihydro-chinoxalin-2-on-hydro- chlorid, 1-(2-Methylsulfonylaminoethyl)-3-(2-thienyi)-1 ,2-dihydrochinoxa-lin-2-on, wie sie in der WO-A-2005/112630 beschrieben sind. S7) Verbindungen der Formel (S7),wie sie in der WO-A- 1998/38856 beschrieben 1-Methyl-3- (2-thienyl) -1,2-dihydroquinoxalin-2-one, 1-methyl-3- (2-thienyl) -1,2-dihydroquinoxaline-2-thione, 1- (2 Aminoethyl) -3- (2-thienyl) -1,2-dihydroquinoxaline-2-one hydrochloride, 1- (2-methylsulfonylaminoethyl) -3- (2-thienyl) -1,2-dihydroquinoxa lin-2-one as described in WO-A-2005/112630. S7) Compounds of the formula (S7) as described in WO-A-1998/38856
sind worin die Symbole und Indizes folgende Bedeutungen haben: RE2 sind unabhängig voneinander Halogen, (Ci-C4)Alkyl, (d-C4)Alkoxy, in which the symbols and indices have the following meanings: RE 2 are, independently of one another, halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) -alkoxy,
(Ci-C4)Haloalkyl, (Ci-C4)Alkylamino, Di-(Ci-C4)Alkylamino, Nitro; (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkylamino, di (C 1 -C 4 ) alkylamino, nitro;
AE ist COORE3 oder COSRE4 A E is COORE 3 or COSRE 4
RE3, RE4 sind unabhängig voneinander Wasserstoff, (d-C4)Alkyl, (C2-Ce)Alkenyl, (C2-C4)Alkinyl, Cyanoalkyl, (Ci-C4)Haloalkyl, Phenyl, Nitrophenyl, Benzyl, Halobenzyl, Pyridinylalkyl und Alkylammonium, RE 3 , RE 4 are, independently of one another, hydrogen, (C 1 -C 4 ) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 4 ) -alkynyl, cyanoalkyl, (C 1 -C 4 ) -haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, Pyridinylalkyl and alkylammonium,
ΠΕ1 ist 0 oder 1 ΠΕ 1 is 0 or 1
ΠΕ2, ΠΕ3 sind unabhängig voneinander 0, 1 oder 2, vorzugsweise Diphenylmethoxyessigsäure, Diphenylmethoxyessigsäureethylester, Diphenyl-methoxyessigsäuremethylester (CAS-Reg.Nr. 41858-19-9) (S7-1 ). ΠΕ 2 , ΠΕ 3 are each independently 0, 1 or 2, preferably diphenylmethoxyacetic acid, ethyl diphenylmethoxyacetate, methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1).
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  Wherein
XF CH oder N, XF CH or N,
nF für den Fall, dass XF=N ist, eine ganze Zahl von 0 bis 4 und nF for the case that XF = N, an integer from 0 to 4 and
für den Fall, dass XF=CH ist, eine ganze Zahl von 0 bis 5 ,  for the case that XF = CH, an integer from 0 to 5,
RF1 Halogen, (Ci-C4)Alkyl, (Ci-C4)Haloalkyl, (Ci-C4)Alkoxy, (Ci-C4)Haloalkoxy, Nitro, (Ci-C4)Alkylthio, (Ci-C4)-Alkylsulfonyl, (Ci-C4)Alkoxycarbonyl, ggf. substituiertes. Phenyl, ggf. substituiertes Phenoxy, RF 1 halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, nitro, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) 4 ) -alkylsulfonyl, (Ci-C 4 ) alkoxycarbonyl, optionally substituted. Phenyl, optionally substituted phenoxy,
RF2 Wasserstoff oder (d-C4)Alkyl RF 2 is hydrogen or (dC 4 ) alkyl
RF3 Wasserstoff, (Ci-C8)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; bedeuten, oder deren Salze, vorzugsweise Verbindungen worin RF 3 is hydrogen, (Ci-C 8 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals unsubstituted or by one or more, preferably substituted into three identical or different radicals from the group consisting of halogen and alkoxy; or their salts, preferably compounds wherein
nF eine ganze Zahl von 0 bis 2 , nF is an integer from 0 to 2,
RF1 Halogen, (Ci-C )Alkyl, (Ci-C )Haloalkyl, (Ci-C )Alkoxy, (d-C4)Haloalkoxy, RF2 Wasserstoff oder (d-C4)Alkyl, RF 1 halogen, (Ci-C) alkyl, (Ci-C) haloalkyl, (Ci-C) alkoxy, (dC 4 ) haloalkoxy, RF 2 hydrogen or (dC 4 ) alkyl,
RF3 Wasserstoff, (Ci-Ce)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, bedeuten, RF 3 is hydrogen, (Ci-Ce) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals unsubstituted or by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy is substituted, mean
oder deren Salze. or their salts.
S9) Wirkstoffe aus der Klasse der 3-(5-Tetrazolylcarbonyl)-2-chinolone (S9), z.B. 1 ,2-Dihydro-4-hydroxy-1 -ethyl-3-(5-tetrazolylcarbonyl)-2-chinolon (CAS-Reg.Nr. S9) Agents from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g. 1, 2-Dihydro-4-hydroxy-1-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg.
219479-18-2), 1 ,2-Dihydro-4-hydroxy-1 -methyl-3-(5-tetrazolyl-carbonyl)-2-chinolon (CAS-Reg.Nr. 95855-00-8), wie sie in der WO-A-1999/000020 beschrieben sind. S10) Verbindungen der Formeln (S 0a) oder (S 0b) 219479-18-2), 1, 2-dihydro-4-hydroxy-1-methyl-3- (5-tetrazolyl-carbonyl) -2-quinolone (CAS Reg. 95855-00-8), as described in WO-A-1999/000020. S10) compounds of the formulas (S 0 a ) or (S 0 b )
wie sie in der WO-A-2007/0237 9 und WO-A-2007/023764 beschrieben sind  as described in WO-A-2007/0237 9 and WO-A-2007/023764
worin  wherein
RG1 Halogen, (Ci-C4)Alkyl, Methoxy, Nitro, Cyano, CF3, OCF3 RG 1 halogen, (C 1 -C 4 ) alkyl, methoxy, nitro, cyano, CF 3 , OCF 3
YG, ZGunabhängig voneinander O oder S,  YG, ZGindependently O or S,
nc eine ganze Zahl von 0 bis 4,  nc is an integer from 0 to 4,
RG2 (Ci-Ci6)Alkyl, (C2-C6)Alkenyl, (C3-C6)Cycloalkyl, Aryl; Benzyl, Halogenbenzyl, RG3 Wasserstoff oder (Ci-Ce)Alkyl bedeutet. RG 2 (Ci-C 6) alkyl, (C2-C6) alkenyl, (C 3 -C 6) cycloalkyl, aryl; Benzyl, halobenzyl, RG 3 is hydrogen or (Ci-Ce) alkyl.
51 1 ) Wirkstoffe vom Typ der Oxyimino-Verbindungen (S1 1 ), die als Saatbeizmittel bekannt sind, wie z. B. "Oxabetrinil" ((Z)-1 ,3-Dioxolan-2-ylmethoxyimino-51 1) Active substances of the type of oxyimino compounds (S1 1), which are known as seed dressing, such. "Oxabetrinil" ((Z) -1,3-dioxolan-2-ylmethoxyimino)
(phenyl)acetonitril) (S11 -1 ), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist, "Fluxofenim" (1 -(4-Chlorphenyl)-2,2,2-trifluor-1 -ethanon-O- (1 ,3-dioxolan-2-ylmethyl)-oxim) (S11 -2), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist, und "Cyometrinil" oder "CGA-43089" ((Z)- Cyanomethoxyimino(phenyl)acetonitril) (S1 1-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist. (phenyl) acetonitrile) (S11-1), which is known as millet safener for millet against damage by metolachlor, "Fluxofenim" (1- (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone-O - (1, 3-dioxolan-2-ylmethyl) -oxime) (S11-2) known as millet safener for millet against damage by metolachlor, and "Cyometrinil" or "CGA-43089" ((Z) - Cyanomethoxyimino (phenyl) acetonitrile) (S1 1-3) known as millet safener for millet against damage by metolachlor.
512) Wirkstoffe aus der Klasse der Isothiochromanone (S12), wie z.B. Methyl-[(3- oxo-1 H-2-benzothiopyran-4(3H)-yliden)methoxy]acetat (CAS-Reg.Nr. 205121 -04-6) (S12-1 ) und verwandte Verbindungen aus WO-A-1998/13361 . 512) Isothiochromanone (S12) class agents, e.g. Methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121 -04-6) (S12-1) and related compounds of WO-A -1998/13361.
513) Eine oder mehrere Verbindungen aus Gruppe (S13): "Naphthalic anhydrid" (1 ,8-Naphthalindicarbonsäureanhydrid) (S13-1 ), das als Saatbeiz-Safener für Mais gegen Schäden von Thiocarbamatherbiziden bekannt ist, "Fenclorim" (4,6-Dichlor-2- phenylpyrimidin) (S13-2), das als Safener für Pretilachlor in gesätem Reis bekannt ist, "F!urazole" (Benzyl-2-chlor-4-trifluormethyl-1 ,3-thiazol-5-carboxylat) (S 3-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Alachlor und Metoiachlor bekannt ist, "CL 304415" (CAS-Reg.Nr. 31541 -57-8) (4-Carboxy-3,4-dihydro-2H-1-benzopyran-4- essigsäure) (S13-4) der Firma American Cyanamid, das als Safener für Mais gegen Schäden von Imidazolinonen bekannt ist, "MG 191" (CAS-Reg.Nr. 96420-72-3) (2- Dichlormethyl-2-methyl-1 ,3-dioxolan) (S13-5) der Firma Nitrokemia, das als Safener für Mais bekannt ist, "MG-838" (CAS-Reg.Nr. 133993-74-5) (2-propenyl 1-oxa-4- azaspiro[4.5]decan-4-carbodithioat) (S13-6) der Firma Nitrokemia, "Disulfoton" (0,0- Diethyl S-2-ethylthioethyl phosphordithioat) (S13-7), "Dietholate" (O,O-Diethyl-O- phenylphosphorothioat) (S13-8), "Mephenate" (4-Chlorphenyl-methylcarbamat) (S13-9). 513) One or more compounds of group (S13): "naphthalene anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), known as a seed safener for corn against damage by thiocarbamate herbicides, "fenclorim" (4,6 Dichloro-2-phenylpyrimidine) (S13-2) known as safener for pretilachlor in sown rice, "F! Urazole" (Benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S 3-3), which is known as a seed-dressing safener for millet against damage by alachlor and metoiachlor, " CL 304415 (CAS No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, available as safener for maize against damage of imidazolinones, "MG 191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, known as corn safener, "MG-838" (CAS Reg. No. 133993-74-5) (2-propenyl 1-oxa-4-azaspiro [4.5] decane-4-carbodithioate) (S13-6 ) from Nitrokemia, "Disulfoton" (O-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7), "Dietholate" (O, O-diethyl-O-phenyl phosphorothioate) (S13-8), "Mephenate" (4-chlorophenyl methylcarbamate) (S13-9).
514) Wirkstoffe, die neben einer herbiziden Wirkung gegen Schadpflanzen auch Safenerwirkung an Kulturpflanzen wie Reis aufweisen, wie z. B. 514) active substances which, in addition to a herbicidal activity against harmful plants, also have safener action on crops such as rice, such as, for example, rice. B.
"Dimepiperate" oder "MY-93" (S-1 -Methyl-1 -phenylethyl-piperidin-1 -carbothioat), das als Safener für Reis gegen Schäden des Herbizids Molinate bekannt ist, "Daimuron" oder "SK 23" (1 -(1 -Methyl-1 -phenylethyl)-3-p-tolyl-harnstoff), das als Safener für Reis gegen Schäden des Herbizids Imazosulfuron bekannt ist, "Cumyluron" = "JC-940" (3- (2-Chlorphenylmethyl)-1 -(1 -methyl-1 -phenyl-ethyl)harnstoff, siehe JP-A-60087254), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "Dimepiperate" or "MY-93" (S-1-methyl-1-phenylethyl-piperidine-1-carbothioate), which is known as a safener for rice against damage by the herbicide Molinate, "daimuron" or "SK 23" (1 - (1-methyl-1-phenylethyl) -3-p-tolyl-urea) known as safener for rice against damage of the herbicide imazosulfuron, "cumyluron" = "JC-940" (3- (2-chlorophenylmethyl) 1 - (1-methyl-1-phenylethyl) urea, see JP-A-60087254), which is known as a safener for rice against damage of some herbicides,
"Methoxyphenon" oder "NK 049" (3,3'-Dimethyl-4-methoxy-benzophenon), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "CSB" (1-Brom-4- (chlormethylsulfonyl)benzol) von Kumiai, (CAS-Reg.Nr. 54091 -06-4), das als Safener gegen Schäden einiger Herbizide in Reis bekannt ist. "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone) known as safener for rice against damage of some herbicides, "COD" (1-bromo-4- (chloromethylsulfonyl) benzene) by Kumiai, (CAS No. 54091 -06-4), known as safener against damage of some herbicides in rice.
515) Verbindungen der Formel (S15) oder deren Tautomere 515) compounds of formula (S15) or their tautomers
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 einen (Ci-C6)Haloalkylrest bedeutet RH2 Wasserstoff oder Halogen bedeutet und wherein a (Ci-C6) haloalkyl radical means RH 2 is hydrogen or halogen and
RH3, RH4 unabhängig voneinander Wasserstoff, (Ci-Ci6)ASkyl, (C2-Cie)Alkenyl oder (C-2-Ci6)Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)Alkoxy, R 3 , R 4 independently of one another denote hydrogen, (C 1 -C 16) alkyl, (C 2 -C 6) alkenyl or (C-2-C 16) alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, Hydroxy, cyano, (C 1 -C 4) alkoxy,
(Ci-C4)Haloalkoxy, (Ci-C4)Alkylthio, (Ci-C4)Alkylamino, Di[(Ci-C4)alkyl]-amino, (Ci-C 4) haloalkoxy, (Ci-C 4) alkylthio, (Ci-C 4) alkylamino, di [(Ci-C 4) alkyl] amino,
[(Ci-C4)Alkoxy]-carbonyl, [(CrC4)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, oder (C3- CeJCycloalkyl, (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, wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (C1 -C4)Alkyl, (C1 -C4)Haloalkyl, (C1 -C4)Alkoxy, (C1 -C4)Haloalkoxy, (C1 -C4)Alkylthio, (C1 -C4)Alkylamino, Di[(C1 - C4)alkyl]-amino, [(C1 -C4)Alkoxy]-carbonyl, [(C1 -C4)Haloalkoxy]-carbonyl, [(C 1 -C 4 ) alkoxy] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl, (C 3 -C 6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted is (C 3 -C 6) cycloalkyl, (C 4 -C 6) cycloalkenyl, (C 3 -C 6) cycloalkyl which is fused on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C 4 -C 6) C6) cycloalkenyl which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, where each of the last-mentioned 4 radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, (C1-6) C4) alkyl, (C1-C4) haloalkyl, (C1-C4) alkoxy, (C1-C4) haloalkoxy, (C1-C4) alkylthio, (C1-C4) alkylamino, di [(C1-C4) alkyl] amino , [(C 1 -C 4) alkoxy] carbonyl, [(C 1 -C 4) 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, bedeutet oder (C 3 -C 6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, or denotes
RH3 (Ci-C4)-Alkoxy, (C2-C4)Alkenyloxy, (C2-C6)Alkinyloxy oder (C2-C4)Haloalkoxy bedeutet und RH 3 (Ci-C 4) alkoxy, (C2-C4) alkenyloxy, (C 2 -C 6) alkynyloxy or (C2-C 4) haloalkoxy group and
RH4 Wasserstoff oder (Ci-C4)-Alkyl bedeutet oder RH 4 is hydrogen or (C 1 -C 4 ) -alkyl or
RH3 und RH4 zusammen mit dem direkt gebundenen N-Atom einen vier- bis RH 3 and RH 4 together with the directly attached N atom have a four-to-one
achtgliedrigen eight-membered
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, (C1- C4)Haloalkoxy und (Ci-C4)Alkylthio substituiert ist, bedeutet. S16) Wirkstoffe, die vorrangig als Herbizide eingesetzt werden, jedoch auch heterocyclic ring which, in addition to the N atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group consisting of N, O and S, and which may be unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, nitro, C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy and (C 1 -C 4 ) -alkylthio is substituted. S16) active substances, which are primarily used as herbicides, but also
Safenerwirkung auf Kulturpflanzen aufweisen, z.B. (2,4-Dichlorphenoxy)essigsäure (2,4-D), (4-Chlorphenoxy)essigsäure, (R,S)-2-(4-Chlor-o-tolyloxy)propionsäure Safeners on crops, e.g. (2,4-dichlorophenoxy) acetic acid (2,4-D), (4-chlorophenoxy) acetic acid, (R, S) -2- (4-chloro-o-tolyloxy) propionic acid
(Mecoprop), 4-(2,4-Dichlorphenoxy)buttersäure (2,4-DB), (4-Chlor-o-tolyloxy)- essigsäure (MCPA), 4-(4-Chlor-o-tolyloxy)buttersäure, 4-(4-Chlorphenoxy)- buttersäure, 3,6-Dichlor-2-methoxybenzoesäure (Dicamba), 1 -(Ethoxycarbonyl)ethyl- 3,6-dichlor-2-methoxybenzoat (Lactidichlor-ethyl). (Mecoprop), 4- (2,4-dichlorophenoxy) butyric acid (2,4-DB), (4-chloro-o-tolyloxy) acetic acid (MCPA), 4- (4-chloro-o-tolyloxy) butyric acid, 4- (4-Chlorophenoxy) butyric acid, 3,6-dichloro-2-methoxybenzoic acid (Dicamba), 1- (ethoxycarbonyl) ethyl-3,6-dichloro-2-methoxybenzoate (lactidichloroethyl).
Pflanzenreife beeinflussende Stoffe: Plant-maturing substances:
Als Kombinationspartner für die Verbindungen der allgemeinen Formel (I) in As a combination partner for the compounds of general formula (I) in
Mischungsformulierungen oder im Tank-Mix sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise 1 -Aminocyclopropan-1 -carboxylatsynthase, 1 -aminocyclopropane-1 -carboxylatoxidase und den Ethylenrezeptoren, z. B. ETR1 , ETR2, ERS1 , ERS2 oder EIN4, beruhen, einsetzbar, wie sie z. B. in Biotechn. Adv. 2006, 24, 357-367; Bot. Bull. Acad. Sin. 199, 40, 1 -7 oder Plant Growth Reg. 1993, 13, 41 -46 und dort zitierter Literatur beschrieben sind. Mixture formulations or in the tank mix are, for example, known active compounds which are based on an inhibition of, for example, 1-aminocyclopropane-1-carboxylate synthase, 1-aminocyclopropane-1-carboxylate oxidase and the ethylene receptors, eg. As ETR1, ETR2, ERS1, ERS2 or EIN4, are based, can be used as z. B. in biotechnology. Adv. 2006, 24, 357-367; Bot. Bull. Acad. Sin. 199, 40, 1-7 or Plant Growth Reg. 1993, 13, 41-46 and references cited therein.
Als bekannte die Pflanzenreife beeinflussende Stoffe, die mit den Verbindungen der allgemeinen Formel (I) kombiniert werden können, sind z.B. folgende Wirkstoffe zu nennen (die Verbindungen sind entweder mit dem "common name" nach der As known plant ripening affecting substances which can be combined with the compounds of the general formula (I) are e.g. to name the following active ingredients (the compounds are either with the "common name" after the
International Organization for Standardization (ISO) oder mit dem chemischen Namen oder mit der Codenummer bezeichnet) und umfassen stets sämtliche International Organization for Standardization (ISO) or with the chemical name or code number) and always include all
Anwendungsformen wie Säuren, Salze, Ester und Isomere wie Stereoisomere und optische Isomere. Dabei sind beispielhaft eine und zum Teil auch mehrere Use forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers. Here are one example and some also several
Anwendungsformen genannt: Application forms called:
Rhizobitoxin, 2-Amino-ethoxy-vinylglycin (AVG), Methoxyvinylglycin (MVG), Rhizobitoxin, 2-amino-ethoxy-vinylglycine (AVG), methoxyvinylglycine (MVG),
Vinylglycin, Aminooxyessigsäure, Sinefungin, S-Adenosylhomocystein, 2-Keto-4- Methylthiobutyrat, (lsopropyliden)-aminooxyessigsäure-2-(methoxy)-2-oxoethylester, (lsopropyliden)-aminooxyessigsäure-2-(hexyloxy)-2-oxoethylester, (Cyclohexylidene)- aminooxyessigsäure-2-(isopropyloxy)-2-oxoethylester, Putrescin, Spermidin, Spermin, 1 ,8-Diamino-4-aminoethyloctan, L-Canalin, Daminozid, 1 -Aminocyclopropyl-1 - carbonsäure-methylester, N-Methyl-1 -aminocyclopropyl-1 -carbonsäure, 1 - Aminocyclopropyl-1 -carbonsäureamid, Substituierte 1 -Aminocyc!opropyl-1 - carbonsäurederivate wie sie in DE3335514, EP30287, DE2906507 oder US5123951 beschrieben werden, 1 -Aminocyc!opropyl-1 -hydroxamsäure, 1 -Methylcyclopropen, 3- Methylcyclopropen, 1 -Ethylcyclopropen, 1 -n-Propyicyclopropen, 1-Cyclopropenyl- Methanol, Carvon, Eugenol, Natriumcycloprop-1 -en-1 -ylacetat, Natriumcycloprop-2-en- 1 -ylacetat, Natrium-3-(cycloprop-2-en-1 -yl)propanoat, Natrium-3-(cycloprop-1 -en-1 - yl)propanoat, Jasmonsäure, Jasmonsäuremethylester, Jasmonsäureethylester. Vinyl glycine, aminooxyacetic acid, sinefungin, S-adenosyl homocysteine, 2-keto-4-methylthiobutyrate, (isopropylidene) aminooxyacetic acid 2- (methoxy) -2-oxoethyl ester, (isopropylidene) aminooxyacetic acid 2- (hexyloxy) -2-oxoethyl ester, (Cyclohexylidenes) - aminooxyacetic acid 2- (isopropyloxy) -2-oxoethyl ester, putrescine, spermidine, spermine, 1, 8-diamino-4-aminoethyloctane, L-canaline, daminozide, 1-aminocyclopropyl-1-carboxylic acid methyl ester, N- Methyl-1-aminocyclopropyl-1-carboxylic acid, 1 - Aminocyclopropyl-1-carboxamide, substituted 1-aminocyclopropyl-1-carboxylic acid derivatives as described in DE3335514, EP30287, DE2906507 or US5123951, 1-aminocyclopropyl-1-hydroxamic acid, 1-methylcyclopropene, 3-methylcyclopropene, 1-ethylcyclopropene , 1 -n-propyicyclopropene, 1-cyclopropenyl-methanol, carvone, eugenol, sodium cycloprop-1 -ene-1-ylacetate, sodium cycloprop-2-ene-1-ylacetate, sodium 3- (cycloprop-2-en-1 - yl) propanoate, sodium 3- (cycloprop-1 -ene-1-yl) propanoate, jasmonic acid, methyl jasmonate, jasmonate.
Pflanzengesundheit und Keimung beeinflussende Stoffe: Plant health and germination affecting substances:
Als Kombinationspartner für die Verbindungen der allgemeinen Formel (I) in As a combination partner for the compounds of general formula (I) in
Mischungsformulierungen oder im Tank-Mix sind beispielsweise bekannte Wirkstoffe, die die Pflanzengesundheit beeinflussen, einsetzbar (die Verbindungen sind entweder mit dem "common name" nach der International Organization for Standardization (ISO) oder mit dem chemischen Namen oder mit der Codenummer bezeichnet und umfassen stets sämtliche Anwendungsformen wie Säuren, Salze, Ester und Isomere wie Stereoisomere und optische Isomere): Sarcosin, Phenylalanin, Tryptophan, N'- Methyl-1-phenyl-1 -N,N-diethylaminomethanesulfonamid, Apio-galacturonane wie sie in WO2010017956 beschrieben werden, 4-Oxo-4-[(2-phenylethyl)amino]butansäure, 4- {[2-(1 H-lndol-3-yl)ethyl]amino}-4-oxobutansäure, 4-[(3-Methylpyridin-2-yl)amino]-4- oxobutansäure, Allantoin, 5-Aminolevulinsäure, (2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4- dihydro-2H-chromen-3,5,7-triol und strukturell verwandte Catechine wie sie in Mixture formulations or in the tank mix, for example, known active ingredients that affect plant health, can be used (the compounds are either with the "common name" according to the International Organization for Standardization (ISO) or with the chemical name or with the code number designated and always include all forms of use, such as acids, salts, esters and isomers, such as stereoisomers and optical isomers): sarcosine, phenylalanine, tryptophan, N'-methyl-1-phenyl-1-N, N-diethylaminomethanesulfonamide, apio-galacturonans as described in WO2010017956, 4-Oxo-4 - [(2-phenylethyl) amino] butanoic acid, 4- {[2- (1H-indol-3-yl) ethyl] amino} -4-oxobutanoic acid, 4 - [(3-methylpyridine-2 -yl) amino] -4-oxobutanoic acid, allantoin, 5-aminolevulinic acid, (2S, 3R) -2- (3,4-dihydroxyphenyl) -3,4-dihydro-2H-chromen-3,5,7-triol and structurally related catechins like those in
WO2010122956 beschrieben werden, 2-Hydroxy-4-(methylsulfanyl)butansäure, (3E,3aR,8ßS)-3-({[(2R)-4-Methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylen)-3,3a,4,8ß- tetrahydro-2H-indeno[1 ,2-b]furan-2-on und analoge Lactone wie sie in EP2248421 beschrieben werden, Abscisinsäure, (2Z,4E)-5-[6-Ethinyl-1 -hydroxy-2,6-dimethyl-4- oxocyclohex-2-en-1 -yl]-3-methylpenta-2,4-diensäure, Methyl-(2Z,4E)-5-[6-ethinyl-1 - hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1 -yl]-3-methylpenta-2,4-dienoat, 4- Phenylbuttersäure, Natrium-4-phenylbutanoat, Kalium-4-phenylbutanoat. WO2010122956, 2-hydroxy-4- (methylsulfanyl) butanoic acid, (3E, 3aR, 8βS) -3 - ({[(2R) -4-methyl-5-oxo-2,5-dihydrofuran-2-yl] oxy} methylene) -3,3a, 4,8β-tetrahydro-2H-indeno [1,2-b] furan-2-one and analogous lactones as described in EP2248421, abscisic acid, (2Z, 4E) -5- [6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl] -3-methyl-penta-2,4-dienoic acid, methyl (2Z, 4E) -5- [6 -ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl] -3-methylpenta-2,4-dienoate, 4-phenylbutyric acid, sodium 4-phenylbutanoate, potassium 4- phenylbutanoate.
Herbizide oder Pflanzenwachstumsregulatoren: Als Kombinationspartner für die Verbindungen der allgemeinen Formel (I) in Herbicides or plant growth regulators: As a combination partner for the compounds of general formula (I) in
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, Mixture formulations or in the tank mix are, for example, known active substances which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase,
Glutamin-Synthetase, p-Hydroxyphenylpyruvat-Dioxygenase, Phytoendesaturase, Photosystem I, Photosystem II, Protoporphyrinogen-Oxidase beruhen, einsetzbar, wie sie z.B. aus Weed Research 26 (1986) 441 -445 oder "The Pesticide Manual", 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 und dort zitierter Literatur beschrieben sind. Glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, can be used, e.g. from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and cited therein.
Als bekannte Herbizide oder Pflanzenwachstumsregulatoren, die mit Verbindungen der allgemeinen Formel (I) kombiniert werden können, sind z.B. folgende Wirkstoffe zu nennen (die Verbindungen sind entweder mit dem "common name" nach der As known herbicides or plant growth regulators which can be combined with compounds of general formula (I), e.g. to name the following active ingredients (the compounds are either with the "common name" after the
International Organization for Standardization (ISO) oder mit dem chemischen Namen oder mit der Codenummer bezeichnet) und umfassen stets sämtliche International Organization for Standardization (ISO) or with the chemical name or code number) and always include all
Anwendungsformen wie Säuren, Salze, Ester und Isomere wie Stereoisomere und optische Isomere. Dabei sind beispielhaft eine und zum Teil auch mehrere  Use forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers. Here are one example and some also several
Anwendungsformen genannt: Acetochlor, Acibenzolar, Acibenzolar-S-methyl, Acifluorfen, Acifluorfen-sodium,Application forms called: Acetochlor, Acibenzolar, Acibenzolar-S-methyl, Acifluorfen, Acifluorfen-sodium,
Aclonifen, Alachlor, Allidochlor, Alloxydim, Alloxydim-sodium, Ametryn, Amicarbazone, Amidochlor, Amidosulfuron, Aminocyclopyrachlor, Aminopyralid, Amitrole, Aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminopyralid, amitrole,
Ammoniumsulfamat, Ancymidol, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Aziprotryn, Beflubutamid, Benazolin, Benazolin-ethyl, Bencarbazone, Benfiuralin, Benfuresate, Bensulide, Bensulfuron, Bensulfuron-methyl, Bentazone, Benzfendizone, Benzobicyclon, Benzofenap, Benzofluor, Benzoylprop, Bicyclopyrone, Bifenox, Bilanafos, Bilanafos-natrium, Bispyribac, Bispyribac-natrium, Bromacil, Bromobutide, Bromofenoxim, Bromoxynil, Bromuron, Buminafos, Busoxinone, Butachlor, Ammonium Sulfamate, Ancymidol, Anilofos, Asulam, Atrazine, Azafenidine, Azimsulfuron, Aziprotryn, Beflubutamide, Benazoline, Benazolin-ethyl, Bencarbazone, Benfiuralin, Benfuresate, Bensulide, Bensulfuron, Bensulfuron-methyl, Bentazone, Benzofendizone, Benzobicyclone, Benzofenap, Benzofluor, Benzoylprop, Bicyclopyrone, Bifenox, Bilanafos, Bilanafos Sodium, Bispyribac, Bispyribac Sodium, Bromacil, Bromobutide, Bromofenoxime, Bromoxynil, Bromuron, Buminafos, Busoxinone, Butachlor,
Butafenacil, Butamifos, Butenachlor, Butralin, Butroxydim, Butylate, Cafenstrole, Carbetamide, Carfentrazone, Carfentrazone-ethyl, Chlomethoxyfen, Chloramben, Chlorazifop, Chlorazifop-butyl, Chlorbromuron, Chlorbufam, Chlorfenac, Chlorfenac- natrium, Chlorfenprop, Chlorflurenol, Chlorflurenol-methyl, Chloridazon, Chlorimuron, Chlorimuron-ethyl, Chlormequat-chlorid, Chlornitrofen, Chlorophthalim, Chlorthal- dimethyl, Chlorotoluron, Chlorsulfuron, Cinidon, Cinidon-ethyl, Cinmethylin, Cinosu!furon, Clethodim, C!odinafop, Clodinafop-propargyl, Clofencet, Clomazone, Clomeprop, Cloprop, Clopyralid, Cloransulam, Cloransulam-methyl, Cumyluron, Cyanamide, Cyanazine, Cyclanilide, Cycloate, Cyclosulfamuron, Cycloxydim, Butafenacil, butamifos, butenachlor, butraline, butroxydim, butylates, cafenstroles, carbetamides, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chloramben, chloroazifop, chlorazifop-butyl, chlorobromuron, chlorobufam, chlorfenac, chlorfenacsodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, Chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat chloride, chloronitrofen, chlorophthalim, chlorothal-dimethyl, chlorotoluron, chlorosulfuron, cinidone, cinidon-ethyl, cinmethylin, Cinosulfon, Clethodim, C! Odinafop, Clodinafop-propargyl, Clofencet, Clomazone, Clomeprop, Cloprop, Clopyralid, Cloransulam, Cloransulam-methyl, Cumyluron, Cyanamide, Cyanazine, Cyclanilide, Cycloate, Cyclosulfamuron, Cycloxydim,
Cycluron, Cyhalofop, Cyhalofop-butyl, Cyperquat, Cyprazine, Cyprazole, 2,4-D, 2,4- DB, Daimuron/Dymron, Dalapon, Daminozid, Dazomet, n-Decanol, Desmedipham, Desmetryn, Detosyl-Pyrazolate (DTP), Diallate, Dicamba, Dichlobenil, Dichlorprop, Dichlorprop-P, Diclofop, Diclofop-methyl, Diclofop-P-methyl, Diclosulam, Diethatyl, Diethatyl-ethyl, Difenoxuron, Difenzoquat, Diflufenican, Diflufenzopyr, Diflufenzopyr- natrium, Dimefuron, Dikegulac-sodium, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimethenamid-P, Dimethipin, Dimetrasulfuron,Cycluron, Cyhalofop, Cyhalofop-butyl, Cyperquat, Cyprazine, Cyprazole, 2,4-D, 2,4-DB, Daimurone / Dymron, Dalapon, Daminozide, Dazomet, n-decanol, Desmedipham, Desmetryn, Detosyl-Pyrazolate (DTP) , Dialkylates, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, diethatyl, diethyl-ethyl, difenoxuron, difenzoquat, diflufenican, difluufenzopyr, difluoropentyrimidate, dimefuron, dikegulac-sodium , Dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipine, dimetrasulfuron,
Dinitramine, Dinoseb, Dinoterb, Diphenamid, Dipropetryn, Diquat, Diquat-dibromide, Dithiopyr, Diuron, DNOC, Eg!inazine-ethyl, Endothal, EPTC, Esprocarb, Ethalfiuralin, Ethametsulfuron, Ethametsulfuron-methyl, Ethephon, Ethidimuron, Ethiozin, Dinitramine, Dinoseb, Dinoterb, Diphenamid, Dipropetryn, Diquat, Diquat-dibromide, Dithiopyr, Diuron, DNOC, Eg! Inazine-ethyl, Endothal, EPTC, Esprocarb, Ethalfiuralin, Ethametsulfuron, Ethametsulfuron-methyl, Ethephon, Ethidimuron, Ethiozine,
Ethofumesate, Ethoxyfen, Ethoxyfen-ethyl, Ethoxysuifuron, Etobenzanid, F-5331 , d.h. N-[2-Chlor-4-fiuor-5-[4-(3-fluorpropyl)-4,5-dihydro-5-oxo-1 H-tetrazol-1-yl]-phenyl]- ethansulfonamid, F-7967, d. h. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-1 H-benzimidazol-4- yl]-1 -methyl-6-(trifluormethyl)pyrimidin-2,4(1 H,3H)-dion, Fenoprop, Fenoxaprop, Fenoxaprop-P, Fenoxaprop-ethyl, Fenoxaprop-P-ethyl, Fenoxasulfone, Fentrazamide, Fenuron, Flamprop, Flamprop-M-isopropyl, Flamprop-M-methyl, Flazasulfuron, Florasulam, Fluazifop, Fluazifop-P, Fluazifop-butyl, Fluazifop-P-butyl, Fluazolate, Flucarbazone, Flucarbazone-sodium, Flucetosulfuron, Fluchloralin, Flufenacet Ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxy-suifuron, etobenzanide, F-5331, i. N- [2-Chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1H-tetrazol-1-yl] -phenyl] -ethanesulfonamide, F-7967 , d. H. 3- [7-chloro-5-fluoro-2- (trifluoromethyl) -1H-benzimidazol-4-yl] -1-methyl-6- (trifluoromethyl) pyrimidine-2,4 (1H, 3H) -dione, Fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fentrazamide, fenuron, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop butyl, fluazifop-p-butyl, fluazolates, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet
(Thiafluamide), Flufenpyr, Flufenpyr-ethyl, Flumetralin, Flumetsulam, Flumiclorac, Flumiclorac-pentyl, Flumioxazin, Flumipropyn, Fluometuron, Fluorodifen, (Thiafluamide), Flufenpyr, Flufenpyr-ethyl, Flumetralin, Flumetsulam, Flumiclorac, Flumiclorac-pentyl, Flumioxazin, Flumipropyn, Fluometuron, Fluorodifen,
Fluoroglycofen, Fluoroglycofen-ethyl, Flupoxam, Flupropacil, Flupropanate, Fluoroglycofen, fluoroglycofen-ethyl, flupoxam, flupropacil, flupropanate,
Flupyrsulfuron, Flupyrsulfuron-methyl-sodium, Flurenol, Flurenol-butyl, Fluridone, Flurochloridone, Fluroxypyr, Fluroxypyr-meptyl, Flurprimidol, Flurtamone, Fluthiacet, Fluthiacet-methyl, Fluthiamide, Fomesafen, Foramsulfuron, Förch lorfenuron, Flupyrsulfuron, flupyrsulfuron-methyl-sodium, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen, foramsulfuron, förch lorfenuron,
Fosamine, Furyloxyfen, Gibberellinsäure, Glufosinate, Glufosinate-ammonium, Glufosinate-P, Glufosinate-P-ammonium, Glufosinate-P-natrium, Glyphosate, Fosamines, furyloxyfen, gibberellic acid, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate,
Glyphosate-isopropylammonium, H-9201 , d. h. 0-(2,4-Dimethyl-6-nitrophenyl)-0-ethyl- isopropylphosphoramidothioat, Halosafen, Halosulfuron, Halosulfuron-methyl, Glyphosate isopropylammonium, H-9201, d. H. 0- (2,4-dimethyl-6-nitrophenyl) -0-ethyl-isopropylphosphoramidothioate, halosafen, halosulfuron, halosulfuron-methyl,
Haloxyfop, Haloxyfop-P, Haloxyfop-ethoxyethyl, Haloxyfop-P-ethoxyethyl, Haloxyfop- methyl, Haloxyfop-P-methyl, Hexazinone, HW-02, d. h. 1 -(Dimethoxyphosphoryl)- ethyl(2,4-dichlorphenoxy)acetat, Imazamethabenz, Imazamethabenz-methyl, Imazamox, Imazamox-ammonium, Imazapic, Imazapyr, Imazapyr- isopropylammonium, Imazaquin, Imazaquin-ammonium, Imazethapyr, Imazethapyr- ammonium, Imazosulfuron, Inabenfide, Indanofan, Indaziflam, Indolessigsäure (IAA), 4-lndol-3-ylbuttersäure (IBA), lodosulfuron, lodosulfuron-methyl-natrium, loxynil, Ipfencarbazone, Isocarbamid, Isopropalin, Isoproturon, Isouron, Isoxaben, Haloxyfop, haloxyfop-P, haloxyfopethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfopmethyl, haloxyfop-P-methyl, hexazinone, HW-02, ie 1- (dimethoxyphosphoryl) ethyl (2,4-dichlorophenoxy) acetate, imazamethabenz , Imazamethabenz-methyl, Imazamox, imazamox-ammonium, imazapic, imazapyr, imazapyrisopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyrammonium, imazosulfuron, inabenfide, indanofan, indaziflam, indoleacetic acid (IAA), 4-indol-3-yl-butyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, loxynil, isoparbazone, isocarbamide, isopropalin, isoproturon, isourone, isoxaben,
Isoxachlortole, Isoxaflutole, Isoxapyrifop, KUH-043, d. h. 3-({[5-(Difluormethyl)-1 - methyl-3-(trifluormethyl)-1 H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1 ,2- oxazol, Karbutilate, Ketospiradox, Lactofen, Lenacil, Linuron, Maleinsäurehydrazid, MCPA, MCPB, MCPB-methyl, -ethyl und -natrium, Mecoprop, Mecoprop-natrium, Mecoprop-butotyi, Mecoprop-P-butotyl, Mecoprop-P-dimethylammonium, Mecoprop-P- 2-ethylhexyl, Mecoprop-P-kalium, Mefenacet, Mefluidide, Mepiquat-chlorid,  Isoxachlortole, Isoxaflutole, Isoxapyrifop, KUH-043, d. H. 3 - ({[5- (Difluoromethyl) -1-methyl-3- (trifluoromethyl) -1H-pyrazol-4-yl] methyl} sulfonyl) -5,5-dimethyl-4,5-dihydro-1,2 - oxazole, carbutilates, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, mecoprop-butotyi, mecoprop-p-butotyl, mecoprop-P-dimethylammonium , Mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide, mepiquat chloride,
Mesosulfuron, Mesosulfuron-methyl, Mesotrione, Methabenzthiazuron, Metam, Mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam,
Metamifop, Metamitron, Metazachlor, Metazasulfuron, Methazole, Methiopyrsulfuron, Methiozolin, Methoxyphenone, Methyldymron, 1 -Methylcyclopropen, Metamifop, metamitron, metazachlor, metazasulfuron, methazole, methiopyrsulfuron, methiozoline, methoxyphenones, methyldymron, 1-methylcyclopropene,
Methylisothiocyanat, Metobenzuron, Metobromuron, Metolachlor, S-Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron, Metsulfuron-methyl, Molinate, Methylisothiocyanate, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinates,
Monalide, Monocarbamide, Monocarbamide-dihydrogensulfat, Monolinuron, Monalides, monocarbamides, monocarbamide dihydrogen sulfate, monolinuron,
Monosulfuron, Monosulfuron-ester, Monuron, MT-128, d. h. 6-Chlor-N-[(2E)-3- chlorprop-2-en-1-yl]-5-methyl-N-phenylpyridazin-3-amin, MT-5950, d. h. N-[3-Chlor-4- (1 -methylethyl)-phenyl]-2-methylpentanamid, NGGC-01 1 , Naproanilide, Napropamide, Naptalam, NC-310, d.h. 4-(2,4-Dichlorobenzoyl)-1 -methyl-5-benzyloxypyrazole, Neburon, Nicosulfuron, Nipyraclofen, Nitralin, Nitrofen, Nitrophenolat-natrium Monosulfuron, Monosulfuron Ester, Monuron, MT-128, d. H. 6-Chloro-N - [(2E) -3-chloroprop-2-en-1-yl] -5-methyl-N-phenylpyridazine-3-amine, MT-5950, d. H. N- [3-chloro-4- (1-methylethyl) phenyl] -2-methylpentanamide, NGGC-01 1, naproanilides, napropamide, naptalam, NC-310, i. 4- (2,4-Dichlorobenzoyl) -1-methyl-5-benzyloxypyrazoles, neburone, nicosulfuron, nipyraclofen, nitrite, nitrofen, nitrophenolate sodium
(Isomerengemisch), Nitrofluorfen, Nonansäure, Norflurazon, Orbencarb, (Mixture of isomers), nitrofluorfen, nonanoic acid, norflurazon, orbencarb,
Orthosulfamuron, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paclobutrazol, Paraquat, Paraquat-dichlorid, Pelargonsäure Orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paclobutrazole, paraquat, paraquat-dichloride, pelargonic acid
(Nonansäure), Pendimethalin, Pendralin, Penoxsulam, Pentanochlor, Pentoxazone, Perfluidone, Pethoxamid, Phenisopham, Phenmedipham, Phenmedipham-ethyl, Picloram, Picolinafen, Pinoxaden, Piperophos, Pirifenop, Pirifenop-butyl, Pretilachlor, Primisulfuron, Primisulfuron-methyl, Probenazole, Profi uazol, Procyazine, Prodiamine, Prifluraline, Profoxydim, Prohexadione, Prohexadione-calcium, Prohydrojasmone, Prometon, Prometryn, Propachlor, Propanil, Propaquizafop, Propazine, Propham, Propisochlor, Propoxycarbazone, Propoxycarbazone-natrium, Propyrisulfuron,  (Nonanoic acid), pendimethalin, pendalkin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamide, phenisopham, phenmedipham, phenmediphamethyl, picloram, picolinafen, pinoxaden, piperophos, pirifenop, pirifenoputyl, pretilachlor, primisulfuron, primisulfuron-methyl, probenazoles, Professional uazole, Procyazine, Prodiamine, Prifluralin, Profoxydim, Prohexadione, Prohexadione-calcium, Prohydrojasmone, Prometon, Prometry, Propachlor, Propanil, Propaquizafop, Propazine, Propham, Propisochlor, Propoxycarbazone, Propoxycarbazone sodium, Propyrisulfuron,
Propyzamide, Prosulfalin, Prosulfocarb, Prosulfuron, Prynachior, Pyraclonil, Pyraflufen, Pyraflufen-ethyl, Pyrasulfotole, Pyrazolynate (Pyrazolate), Pyrazosulfuron, Pyrazosu!furon-ethyl, Pyrazoxyfen, Pyribambenz, Pyribambenz-isopropyl, Pyribambenz-propyl, Pyribenzoxim, Pyributicarb, Pyridafol, Pyridate, Pyriftalid, Propyzamide, Prosulfine, Prosulfocarb, Prosulfuron, Prynachior, Pyraclonil, Pyraflufen, Pyraflufen-ethyl, Pyrasulfotole, Pyrazolynate (Pyrazolate), Pyrazosulfuron, Pyrazosugaron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxime, pyributicarb, pyridafol, pyridate, pyridalid,
Pyriminobac, Pyriminobac-methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac-natrium, Pyroxasulfone, Pyroxsulam, Quinclorac, Quinmerac, Quinoclamine, Quizalofop, Quizalofop-ethyl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Rimsuifuron, Saflufenacil, Secbumeton, Sethoxydim, Siduron, Simazine, Simetryn, SN-106279, d. h. Methyl-(2R)-2-({7-[2-chlor-4-(trifluormethyl)phenoxy]-2-naphthyl}oxy)-propanoat, Sulcotrione, Sulfallate (CDEC), Sulfentrazone, Sulfometuron, Sulfometuron-methyl, Sulfosate (Glyphosate-trimesium), Sulfosulfuron, SYN-523, SYP-249, d. h. 1-Ethoxy-3- methyl-1 -oxobut-3-en-2-yl-5-[2-chlor-4-(trifluormethyl)phenoxy]-2-nitrobenzoat, SYP- 300, d. h. 1 -[7-Fluor-3-oxo-4-(prop-2-in-1 -yl)-3,4-dihydro-2H- ,4-benzoxazin-6-yl]-3- propyl-2-thioxoimidazolidin-4,5-dion, Tebutam, Tebuthiuron, Tecnazene, Tefuryltrione, Tembotrione, Tepraloxydim, Terbacil, Terbucarb, Terbuchlor, Terbumeton, Pyriminobac, Pyriminobac-methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac Sodium, Pyroxasulfones, Pyroxsulam, Quinclorac, Quinmerac, Quinoclamine, Quizalofop, Quizalofop-ethyl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Rimsuifuron, Saflufenacil, Secbumeton, Sethoxydim, Siduron, Simazine, Simetryn, SN-106279, d. H. Methyl (2R) -2 - ({7- [2-chloro-4- (trifluoromethyl) phenoxy] -2-naphthyl} oxy) -propanoate, Sulcotrione, Sulphates (CDEC), Sulfentrazone, Sulfometuron, Sulfometuron-methyl, Sulfosate (Glyphosate trimesium), sulfosulfuron, SYN-523, SYP-249, d. H. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl-5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzoate, SYP-300, d. H. 1 - [7-Fluoro-3-oxo-4- (prop-2-yn-1-yl) -3,4-dihydro-2H, 4-benzoxazin-6-yl] -3-propyl-2-thioxoimidazolidine -4,5-dione, tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton,
Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazafluron, Thiazopyr, Terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazafluron, thiazopyr,
Thidiazimin, Thidiazuron, Thiencarbazone, Thiencarbazone-methyl, Thifensulfuron, Thifensulfuron-methyl, Thiobencarb, Thiocarbazil, Topramezone, Tralkoxydim, Thidiazimine, thidiazuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, thiocarbazil, topramezone, tralkoxydim,
Triallate, Triasulfuron, Triaziflam, Triazofenamide, Tribenuron, Tribenuron-methyl, Trichloressigsäure (TCA), Triclopyr, Tridiphane, Trietazine, Trifloxysulfuron, Triallate, triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine, trifloxysulfuron,
Trifloxysulfuron-natrium, Trifluralin, Triflusulfuron, Triflusulfuron-methyl, Trimeturon, Trinexapac, Trinexapac-ethyl, Tritosulfuron, Tsitodef, Uniconazole, Uniconazole-P, Vernolate, ZJ-0862, d. h. 3,4-Dichlor-N-{2-[(4,6-dimethoxypyrimidin-2- yl)oxy]benzyl}anilin, sowie die folgenden Verbindungen: Trifloxysulfuron Sodium, Trifluralin, Triflusulfuron, Triflusulfuron-methyl, Trimeturon, Trinexapac, Trinexapac-ethyl, Tritosulfuron, Tsitodef, Uniconazole, Uniconazole-P, Vernolate, ZJ-0862, d. H. 3,4-Dichloro-N- {2 - [(4,6-dimethoxypyrimidin-2-yl) oxy] benzyl} aniline, and the following compounds:
Die Erfindung so!! durch die nachfolgenden biologischen Beispiele veranschaulicht werden, ohne sie jedoch darauf einzuschränken. The invention so !! are illustrated by the following biological examples, but without being limited thereto.
Biologische Beispiele: Biological examples:
Samen von mono- bzw. dikotylen Kulturpflanzen wurden in Holzfasertöpfen in sandigem Lehmboden ausgelegt, mit Erde oder Sand abgedeckt und im Gewächshaus unter guten Wachstumsbedingungen angezogen. Die Behandlung der Seeds of monocotyledonous or dicotyledonous crops were placed in sandy loam soil in wood fiber pots, covered with soil or sand, and grown in the greenhouse under good growth conditions. The treatment of
Versuchspflanzen erfolgte im frühen Laubblattstadium (BBCH10 - BBCH13). Zur Gewährleistung einer uniformen Wasserversorgung vor Stressbeginn wurden die bepflanzten Töpfe vor Substanzapplikation durch Anstaubewässerung mit Wasser versorgt. Die in Form von benetzbaren Pulvern (WP) formulierten erfindungsgemässen Verbindungen wurden als wässrige Suspension mit einer Wasseraufwandmenge von umgerechnet 600 l/ha unter Zusatz von 0,2% Netzmittel (z.B. Ag rotin) auf die grünen Pflanzenteile gesprüht. Unmittelbar nach Substanzapplikation erfolgte die Test plants took place in the early leaves leaf stage (BBCH10 - BBCH13). To ensure a uniform water supply before the onset of stress, the planted pots were supplied with water before being applied with substance by means of dewatering. The compounds according to the invention formulated as wettable powders (WP) were sprayed onto the green parts of plants as an aqueous suspension at a rate of 600 l / ha, with the addition of 0.2% wetting agent (for example Ag rotin). Immediately after substance administration was the
Stressbehandlung der Pflanzen. Dazu wurden die Töpfe in Plastikeinsätze transferiert, um anschließendes, zu schnelles Abtrocknen zu verhindern. Der Trockenstress wurde durch langsames Abtrocknen unter folgenden Bedingungen induziert: „Tag": 14 Stunden beleuchtet bei 26°C  Stress treatment of the plants. For this purpose, the pots were transferred to plastic inserts to prevent subsequent, too rapid drying. Drought stress was induced by slow drying under the following conditions: "day": 14 hours illuminated at 26 ° C
„Nacht": 10 Stunden ohne Beleuchtung bei 18°C.  "Night": 10 hours without lighting at 18 ° C.
Die Dauer der jeweiligen Stressphasen richtete sich hauptsächlich nach dem Zustand der unbehandelten, gestressten Kontrollpflanzen und variierte somit von Kultur zu Kultur. Sie wurde (durch Wiederbewässerung und. Transfer in ein Gewächshaus mit guten Wachstumsbedingungen) beendet, sobald irreversible Schäden an den unbehandelten, gestressten Kontrollpflanzen zu beobachten waren. Bei dikotylen Kulturen wie beispielsweise Raps und Soja variierte die Dauer der The duration of the respective stress phases was mainly dependent on the condition of the untreated, stressed control plants and thus varied from culture to culture. It was terminated (by irrigation and transfer to a greenhouse with good growth conditions) as soon as irreversible damage to the untreated, stressed control plants was observed. For dicotyledonous crops such as oilseed rape and soybean, the duration of the diet varied
Trockenstressphase zwischen 3 und 6 Tagen, bei monokotylen Kulturen wie beispielweise Weizen, Gerste oder Mais zwischen 6 und 11 Tagen. Drought phase between 3 and 6 days, in monocotyledonous crops such as wheat, barley or maize between 6 and 11 days.
Nach Beendigung der Stressphase folgte eine ca. 5-7 tägige Erholungsphase, während der die Pflanzen abermals unter guten Wachstumsbedingungen im After completion of the stress phase followed by a 5-7 day recovery period during which the plants again under good growth conditions in
Gewächshaus gehalten wurden. Um auszuschließen, dass die beobachteten Effekte von der ggf. fungiziden oder Insektiziden Wirkung der Testverbindungen beeinflusst wurden, wurde zudem darauf geachtet, dass die Versuche ohne Pilzinfektion oder Insektenbefall abliefen. Greenhouse were kept. In order to rule out that the observed effects were influenced by the possibly fungicidal or insecticidal activity of the test compounds, care was also taken that the experiments proceeded without fungus infection or insect infestation.
Nach Beendigung der Erholungsphase wurden die Schadintensitäten visuell im After completion of the recovery phase, the damage intensities were visually im
Vergleich zu unbehandelten, ungestressten Kontrollen gleichen Alters bonitiert. Die Erfassung der Schadintensität erfolgte zunächst prozentual (100% = Pflanzen sind abgestorben, 0 % = wie Kontrollpflanzen). Aus diesen Werten wurde sodann der Wirkungsgrad der Testverbindungen (= prozentuale Reduktion der Schadintensität durch Substanzapplikation) nach folgender Formel ermittelt: Compared to untreated, unstressed controls of the same age. The detection of the damage intensity was initially percentage (100% = plants are dead, 0% = as control plants). From these values, the efficiency of the test compounds (= percentage reduction of the damage intensity by substance application) was then determined according to the following formula:
WG: Wirkungsgrad (%) WG: Efficiency (%)
SWug: Schadwert der unbehandelten, gestressten Kontrolle  SWug: Damage value of untreated, stressed control
SWbg: Schadwert der mit Testverbindung behandelten Pflanzen In jedem Versuch wurden pro Kultur und Dosierung 3 Töpfe behandelt und SWbg: Damage of test compound treated plants In each experiment, 3 pots were treated per culture and dosage and
ausgewertet, bei den resultierenden Wirkungsgraden handelt es sich also um evaluated, so the resulting efficiencies are
Mittelwerte. Die in den unten stehenden Tabellen A-1 bis A-4 angegebenen Werte sind wiederum Mittelwerte aus ein bis drei unabhängigen Versuchen. Averages. Again, the values given in Tables A-1 through A-4 below are averages of one to three independent experiments.
Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) unter Effects of selected compounds of general formula (I) under
Trockenstress: Tabe!Se A- Drought Stress: Tabe! Se A-
Tabelle A-2Table A-2
Tabelle A-3 Tabelle A-4 Table A-3 Table A-4
In den zuvor genannten Tabellen bedeuten: BRSNS Brassica napus In the aforementioned tables mean: BRSNS Brassica napus
HORVS Hordeum vulgare Horvs Hordeum vulgare
TRZAS Triticum aestivum TRZAS Triticum aestivum
ZEAMX Zea mays Ähnliche Ergebnisse konnten auch noch mit weiteren Verbindungen der allgemeinen Formel (I) auch bei Applikation auf andere Pflanzenarten erzielt werden. ZEAMX Zea mays Similar results could also be achieved with other compounds of the general formula (I) even when applied to other plant species.

Claims

Patentansprüche claims
1 . Verwendung substituierter 2-Amidobenzimidazole, 2-Amidobenzoxazole und 2- Amidobenzothiazole der allgemeinen Formel (I) oder deren Salze 1 . Use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles of the general formula (I) or salts thereof
zur Toleranzerhöhung gegenüber abiotischem Stress in Pflanzen, wobei to increase tolerance to abiotic stress in plants, wherein
R1, R2, R3 unabhängig voneinander für Wasserstoff, Halogen, Alkyl, Cycloalkyl, Cycloalkenyl, Halocycloalkyl, Alkenyl, Alkinyl, Aryl, Arylalkyl, Arylalkenyl, Heteroaryl, Heteroarylalkyl, Heterocyclyl, Heterocyclylalkyl, Alkoxyalkyl, Alkylthio, Haloalkylthio, Haloalkyl, Alkoxy, Haloalkoxy, Cycloalkoxy, Cycloalkylalkoxy, Aryloxy, Heteroraryloxy, Alkoxyalkoxy, Alkinylalkoxy, Alkenyloxy, Bis-alkylaminoalkoxy, Tris-[alkyl]silyl, Bis-[alkyl]arylsilyl, Bis- [alkyl]alkylsilyl, Tris-[alkyl]silylalkinyl, Arylalkinyl, Heteroarylalkinyl, Alkylalkinyl, Cycloalkylalkinyl, Haloalkylalkinyl, Heterocyclyl-N-alkoxy, Nitro, Cyano, Amino, Alkylamino, Bis-alkylamino, Aikylcarbonylamino, Cycloalkylcarbonylamino, Arylcarbonylamino, Alkoxycarbonylamino, Heteroarylalkoxy, Arylalkoxy, Heterocyclylalkoxy, Cycloalkylalkyl, Haloalkenyl, Haloalkinyl, Heterocyclylalkinyl, Halocycloalkoxy, R 1 , R 2 , R 3 are each independently hydrogen, halogen, alkyl, cycloalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy , Haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris [alkyl] silyl, bis [alkyl] arylsilyl, bis [alkyl] alkylsilyl, tris [alkyl] silylalkynyl, arylalkynyl , Heteroarylalkynyl, alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bisalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, heteroarylalkoxy, arylalkoxy, heterocyclylalkoxy, cycloalkylalkyl, haloalkenyl, haloalkynyl, heterocyclylalkynyl, halocycloalkoxy .
Haloalkinyloxy, Arylthio, Heteroarylthio, Alkylsulfinyl, Haloalkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, Alkylsulfonyl, Haloalkylsulfonyl,  Haloalkynyloxy, arylthio, heteroarylthio, alkylsulfinyl, haloalkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,
Arylsulfonyl, Heteroarylsulfonyl, Thiocyanato, Isothiocyanato, Cycloalkylamino, Cycloalkyl(alkyl)amino, Alkenylamino stehen,  Arylsulfonyl, heteroarylsulfonyl, thiocyanato, isothiocyanato, cycloalkylamino, cycloalkyl (alkyl) amino, alkenylamino,
R1 und R2 mit den Atomen, an die sie gebunden sind, einen vollständig R 1 and R 2 with the atoms to which they are attached, a complete
gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, R2 und R3 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, für Sauerstoff, Schwefel steht, für Sauerstoff, Schwefel, N-R4 steht, für Wasserstoff, Alkyl, Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl, form saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring, R 2 and R 3 with the atoms to which they are attached form a completely saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring, represents oxygen, sulfur, oxygen, sulfur, NR 4 is hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl,
Cyanoalkyl, Alkenylalkyl, Haloalkyl, Alkinylalkyl, Arylalkyl, Heteroarylalkyl, Heterocyclylalkyl, Alkylcarbonyl, Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, Haloalkylcarbonyl, Heterocyclylcarbonyl,  Cyanoalkyl, alkenylalkyl, haloalkyl, alkynylalkyl, arylalkyl, heteroarylalkyl, heterocyclylalkyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, haloalkylcarbonyl, heterocyclylcarbonyl,
Arylalkylcarbonyl, Alkoxycarbonyl, Cycloalkylalkoxycarbonyl,  Arylalkylcarbonyl, alkoxycarbonyl, cycloalkylalkoxycarbonyl,
Cycloalkoxycarbonyl, Alkoxycarbonylalkyl, Alkylsulfonyl,  Cycloalkoxycarbonyl, alkoxycarbonylalkyl, alkylsulfonyl,
Cycloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl,  Cycloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl,
Alkoxycarbonylcarbonyl, Arylalkoxycarbonylcarbonyl,  Alkoxycarbonylcarbonyl, arylalkoxycarbonylcarbonyl,
Alkylaminothiocarbonyl, Alkylaminocarbonyl, Cycloalkylaminocarbonyl, Alkoxyalkyl, Bis-[Alkyl]aminocarbonyl, Aryl, Heteroaryl, Heterocyclyl, Cycloalkoxycarbonylalkyl steht,  Alkylaminothiocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, alkoxyalkyl, bis- [alkyl] aminocarbonyl, aryl, heteroaryl, heterocyclyl, cycloalkoxycarbonylalkyl,
Q für Alkyl, Alkenyl, Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl, Aryl, Arylalkyl, Heteroarylalkyl, Heterocyclylalkyl, Heteroaryl, Heterocyclyl, Q is alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, aryl, arylalkyl, heteroarylalkyl, heterocyclylalkyl, heteroaryl, heterocyclyl,
Heterocyclylaryl, Heterocyclylheteroaryl, Heteroarylheteroaryl,  Heterocyclylaryl, heterocyclylheteroaryl, heteroarylheteroaryl,
Heteroarylaryl, Arylaryl, Aryloxyaryl, Arylalkenyl, Heteroarylalkenyl, Heterocyclylalkenyl, Arylalkinyl, Heteroarylalkinyl, Heterocyclylalkinyl, Cycloalkylalkinyl, Alkylaminoalkyl, Bis-alkylaminoalkyl, Hydroxyalkyl, Alkoxyalkyl, Tris-[alkyl]silyloxyalkyl, Bis-[alkyl]arylsilyloxyalkyl, Bis- [alkyl]alkylsilyloxyalkyl, Bis-alkylaminoalkoxyalkyl, Alkoxyalkoxyalkyl, Heteroarylaryl, arylaryl, aryloxyaryl, arylalkenyl, heteroarylalkenyl, heterocyclylalkenyl, arylalkynyl, heteroarylalkynyl, heterocyclylalkynyl, cycloalkylalkynyl, alkylaminoalkyl, bisalkylaminoalkyl, hydroxyalkyl, alkoxyalkyl, tris [alkyl] silyloxyalkyl, bis [alkyl] arylsilyloxyalkyl, bis [alkyl] alkylsilyloxyalkyl , Bis-alkylaminoalkoxyalkyl, alkoxyalkoxyalkyl,
Aryloxyalkyl, Heteroaryloxyalkyl, Alkylthioalkyl, Arylthioalkyl, Aryloxyalkyl, heteroaryloxyalkyl, alkylthioalkyl, arylthioalkyl,
Heteroarylthioalkyl, Alkoxycarbonyl-N-heterocyclyl, Arylalkoxycarbonyl-N- heterocyclyl, Alkyl-N-heterocyclyl, Alkylsulfonyl-N-heterocyclyl,  Heteroarylthioalkyl, alkoxycarbonyl-N-heterocyclyl, arylalkoxycarbonyl-N-heterocyclyl, alkyl-N-heterocyclyl, alkylsulfonyl-N-heterocyclyl,
Arylsulfonyl-N-heterocyclyl, Heteroarylsulfonyl-N-heterocyclyl, Cyc!oalkylsu!fonyl-N-heterocyclyl, Haloalkylsu!fonyl-N-heterocyclyl, Alkylcarbony!-N-heterocyclyl, Arylcarbonyl-N-heterocyclyl, Arylsulfonyl-N-heterocyclyl, heteroarylsulfonyl-N-heterocyclyl, Cycloalkylsulfonyl-N-heterocyclyl, haloalkylsulfonyl-N-heterocyclyl, alkylcarbonyl-N-heterocyclyl, arylcarbonyl-N-heterocyclyl,
Heteroarylcarbonyl-N-heterocyclyl, Cyc!oalkylcarbonyl-N-heterocyclyl, Cycloa!kyl-N-heterocyclyl, Aryl-N-heterocyclyl, Aryla!kyl-N-heterocyclyl, Bis-alkylaminoalkyl-N-heterocyclyl, Bis-alkylaminosu!fonyl-N-heterocyclyl, Heteroaryloxyaryl, Heteroaryloxyheteroaryl, Aryloxyheteroaryl, Heteroarylcarbonyl-N-heterocyclyl, cycloalkylcarbonyl-N-heterocyclyl, cycloalkyl-N-heterocyclyl, aryl-N-heterocyclyl, arylalkyl-N-heterocyclyl, bis-alkylaminoalkyl-N-heterocyclyl, bis-alkylaminosulfonyl- N-heterocyclyl, heteroaryloxyaryl, heteroaryloxyheteroaryl, aryloxyheteroaryl,
Alkylsulfinyl, Alkylthio, Alkylsulfonyl, Cycloalkylsulfinyl, Cycloalkylthio, Cycloalkylsulfonyl, Arylsulfinyl, Arylthio, Arylsulfonyl, Amino, Alkylamino, Arylamino, Arylalkylamino, Cycloa!kylamino, Formyl, Alkylcarbonyl, Arylcarbonyl, Iminoalkyl, Alkyliminoalkyl, Aryliminoa!kyl, Alkoxycarbonyl, Cycloalkoxycarbonyl, Cycloalkyla!koxycarbonyl, Arylalkoxycarbonyl, Arylalkylaminocarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Alkylsulfinyl, alkylthio, alkylsulfonyl, cycloalkylsulfinyl, cycloalkylthio, cycloalkylsulfonyl, arylsulfinyl, arylthio, arylsulfonyl, amino, alkylamino, arylamino, arylalkylamino, cycloalkylamino, formyl, alkylcarbonyl, arylcarbonyl, iminoalkyl, alkyliminoalkyl, aryliminoalkyl, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkyla! koxycarbonyl, arylalkoxycarbonyl, arylalkylaminocarbonyl, aminocarbonyl, alkylaminocarbonyl,
Cycloalkylaminocarbonyl, Bis-alkylaminocarbonyl Heterocyclyl-N- carbonyl, Imino, Alkylimino, Arylimino, Cycloalkylimino, Cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heterocyclyl-N-carbonyl, imino, alkylimino, arylimino, cycloalkylimino,
Cycloalkylalkylimino, Hydroxyimino, Alkoxyimino, Cycloalkoxyimino, Cyloalkylalkoxyimino, Heteroaryloxyimino, Aryloxyimino, Arylalkoxyimino, Alkenyloxyimino, Heteroarylalkoxyimino, Heteroarylimino, Cycloalkylalkylimino, hydroxyimino, alkoxyimino, cycloalkoxyimino, cyloalkylalkoxyimino, heteroaryloxyimino, aryloxyimino, arylalkoxyimino, alkenyloxyimino, heteroarylalkoxyimino, heteroarylimino,
Heterocyclylimino, Heterocycly!alkylimino, Aminoimino, Aikylaminoimino, Aryiaminoimino, Heteroaryiaminoimino, Cycloalkyiaminoimino, Bis- Alkylaminoimino, Arylalkylaminoimino, Aryl(alkyl)aminoimino, Heterocyclylimino, heterocyclylalkylimino, aminoimino, aikylaminoimino, aryiaminoimino, heteroaryiaminoimino, cycloalkyiaminoimino, bis-alkylaminoimino, arylalkylaminoimino, aryl (alkyl) aminoimino,
Cycloalkyl(alkyl)aminoimino, Cycloaikylalkyiaminoimino, Cycloalkyl (alkyl) aminoimino, cycloalkylalkyiaminoimino,
Heterocyclylaminoimino, Heteroarylalkoxyalkyl, Arylaikoxyalkyi, Heterocyclylaminoimino, heteroarylalkoxyalkyl, arylalkoxyalkyi,
Heterocyclyi-N-alkyi, Aryl(aikyi)aminoalkyi, Ary!alkyl(alkyl)aminoaikyl, Alkoxycarbonylaikylaminoaikyl, Alkoxycarbonylalkyl(alkyl)aminoalkyi, Heteroaryl(alkyl)aminoalkyl, Heteroaryiaikyl(alkyl)aminoalkyl, Heterocyclyl-N-alkyl, aryl (aikyl) aminoalkyl, arylalkyl (alkyl) aminoalkyl, alkoxycarbonylalkylaminoalkyl, alkoxycarbonylalkyl (alkyl) aminoalkyl, heteroaryl (alkyl) aminoalkyl, heteroaryiaalkyl (alkyl) aminoalkyl,
Cycloalkyl(alkyl)aminoaikyl, Cycloalkyiaminoalkyl, Alkoxy(alkoxy)alkyl, Arylaikoxyalkyiaryl, Heterocyclyl-N-alkyiaryl, Aryl(alkyl)aminoaikylaryl, Aryialkyi(alkyl)aminoalkylaryl, Alkoxycarbonylalkylaminoalkyiaryl, Cycloalkyl (alkyl) aminoalkyl, cycloalkylaminoalkyl, alkoxy (alkoxy) alkyl, arylalkoxyalkyiaryl, heterocyclyl-N-alkylaryl, aryl (alkyl) aminoalkylaryl, arylalkyl (amino) alkylaryl, alkoxycarbonylalkylaminoalkylglyl,
Alkoxycarbonylalkyi(alkyl)aminoalkylaryl, Heteroaryl(alkyl)aminoalkylaryl, Heteroarylaikyl(alkyl)aminoalkyiaryl, Cycioalkyi(alkyi)aminoalkylaryl, Cycloalkylaminoalkylaryi, Alkoxy(aikoxy)alkylaryi steht, Q zusätzlich, wenn X für ein Sauerstoffatom oder X für ein Schwefelatom steht, für HaSoalkyl, Alkoxyhaloalkyl, HalocycSoalkyl, Haloalkoxyhaloalkyl, Arylhaloalkyl, Alkylthiohaloalkyl, Bisalkylaminoalkoxyhaloalkyl steht, Alkoxycarbonylalkyl (alkyl) aminoalkylaryl, heteroaryl (alkyl) aminoalkylaryl, heteroarylaikyl (alkyl) aminoalkylaryl, cycloalkyl (alkyl) aminoalkylaryl, cycloalkylaminoalkylaryl, alkoxy (aikoxy) alkylaryi, Q additionally, when X represents an oxygen atom or X represents a sulfur atom, represents haloalkyl, alkoxyhaloalkyl, halocycsoalkyl, haloalkoxyhaloalkyl, arylhaloalkyl, alkylthiohaloalkyl, bisalkylaminoalkoxyhaloalkyl,
Z1 für Wasserstoff, Hydroxy, Alkyl, Cycloalkyl, Halocycloalkyl, Halogen, Alkenylalkyl, Haloalkyl, Alkinyl, Alkenyl, Cyanoalkyl, Nitroalkyl, Z 1 is hydrogen, hydroxy, alkyl, cycloalkyl, halocycloalkyl, halogen, alkenylalkyl, haloalkyl, alkynyl, alkenyl, cyanoalkyl, nitroalkyl,
AminoaSkyl, Alkylaminoalkyl, Bis-[Alkyl]aminoalkyl, Alkinylalkyl, Arylalkyl, Heteroarylalkyl, Heterocyclylalkyl, Alkylcarbonyl, Alkoxycarbonyl, Cycloalkoxycarbonyl, Alkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, Cycloalkylsulfonyl, Alkylsulfinyl, Arylsulfinyl, Cycloalkylsulfinyl,  Aminoalkyl, alkylaminoalkyl, bis- [alkyl] aminoalkyl, alkynylalkyl, arylalkyl, heteroarylalkyl, heterocyclylalkyl, alkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, alkylsulfinyl, arylsulfinyl, cycloalkylsulfinyl,
Alkoxycarbonylalkyl, Aryl, Heteroaryl, Heterocyclyl, Aminocarbonylalkyl, Alkylaminocarbonylalkyl, Bisalkylaminocarbonylalkyl,  Alkoxycarbonylalkyl, aryl, heteroaryl, heterocyclyl, aminocarbonylalkyl, alkylaminocarbonylalkyl, bisalkylaminocarbonylalkyl,
Cycloalkylaminocarbonylalkyl, Hydroxycarbonylalkyl, Amino, Alkylamino, Arylamino, Alkoxy, Cycloalkylalkyl steht und  Cycloalkylaminocarbonylalkyl, hydroxycarbonylalkyl, amino, alkylamino, arylamino, alkoxy, cycloalkylalkyl and
Z2 für Wasserstoff, Alkyl, Cycloalkyl, verzweigtes oder unverzweigtes Z 2 is hydrogen, alkyl, cycloalkyl, branched or unbranched
Halogenalkyl, Alkinyl, Alkenyl, Cyanoalkyl, Arylalkyl, Heteroarylalkyl, Alkylcarbonyl, Alkoxycarbonyl steht oder  Haloalkyl, alkynyl, alkenyl, cyanoalkyl, arylalkyl, heteroarylalkyl, alkylcarbonyl, alkoxycarbonyl or
Z1 und Z2 zusammen mit dem Atomen, an das sie gebunden sind, einen Z 1 and Z 2 together with the atom to which they are attached, one
vollständig gesättigten oder teilgesättigten, gegebenenfalls durch  fully saturated or partially saturated, if necessary
Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden oder  Heteroatome form interrupted and optionally further substituted 5 to 7-membered ring or
Z1 und Z2 zusammen Bestandteil einer gegebenenfalls substituierten Sulfilimin- oder Amidingruppe sind oder ein Iminophosphoran bilden. Z 1 and Z 2 together are part of an optionally substituted Sulfilimin- or amidine group or form a iminophosphorane.
2. Verwendung gemäß Anspruch 1 , wobei in Formel (I) 2. Use according to claim 1, wherein in formula (I)
R\ R2, R3 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C8)-Alkyl,R 1 , R 3 independently of one another represent hydrogen, halogen, (C 1 -C 8 ) -alkyl,
(C3-C8)-Cycloalkyl, (C4-C8)-Cycloalkenyl, (C3-C8)-Halocycloalkyl, (C2-C8)- Alkenyl, (C2-C8)-Alkinyl, gegebenenfalls substituiertes Phenyl, Aryl- (Ci-C8)-alkyl, Aryl-(C2-C8)-alkenyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio, (d-C8)-Haloalkylthio, (Ci-C8)-Haloalkyl, (Ci-C8)-Alkoxy, (Ci-Cs)-Haloalkoxy, (C3-C8)-Cycloalkoxy, (C3-C8)-Cycloalkyl-(Ci-C8)- alkoxy, Aryloxy, Heteroraryloxy, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy, (C2-C8)- Alkinyl-(Ci-C8)-alkoxy, (C2-C8)-Alkenyloxy, Bis-[(Ci-C8)-alkyl]amino- (Ci-C8)-alkoxy, Tris-[(Ci-C8)-alkyl]silyl, Bis-[(Ci-C8)-alkyl]arylsilyl, Bis- [(Ci-C8)-alkyl]-(Ci-C8)-alkylsilyl, Tris-[(Ci-C8)-alkyl]silyl-(C2-C8)-alkinyl, Aryl-(C2-C8)-alkinyl, Heteroaryl-(C2-C8)-alkinyl, (Ci-C8)-Alkyl-(C2-C8)- alkinyl, (C3-C8)-Cycloalkyl-(C2-C8)-alkinyl, (Ci-C8)-Haloalkyl-(C2-C8)- alkinyl, Heterocyclyl-N-(Ci-C8)-alkoxy, Nitro, Cyano, Amino, (Ci-C8)- Alkylamino, Bis-[(Ci-C8)-alkyl]amino, (Ci-C8)- Alkylcarbonylamino, (C3-C8)-Cycloalkylcarbonylamino, Arylcarbonylamino, (d-C8)- Alkoxycarbonylamino, Heterocyclyl-(Ci-C8)-alkoxy, (C3-C8)- Cycloalkyl- (Ci-Cs)-alkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, Heterocyclyl- (C2-C8)-alkinyl, (C3-C8)-Halocycloalkoxy, (C2-C8)-Haloalkinyloxy, Arylthio, Heteroarylthio, (Ci-Cs)-Alkylsulfinyl, (Ci-Cs)-Haloalkylsulfinyl, Arylsulfinyl, Heteroarylsulfinyl, (Ci-Cs)-Alkylsulfonyl, (Ci-C8)-Haloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, Thiocyanato, Isothiocyanato, (C3-C8)- Cycloalkylamino, (C3-C8)-Cycloalkyl[(Ci-C8)-alkyl]amino, (C2-C8)- Alkenylamino stehen, (C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C 3 -C 8 ) -halocycloalkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, optionally substituted phenyl, aryl- (Ci-C 8) alkyl, aryl (C 2 -C 8) alkenyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, heterocyclyl, heterocyclyl (Ci-C8) - alkyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C8) alkylthio, (dC 8) haloalkylthio, (Ci-C 8) haloalkyl, (Ci-C 8 ) alkoxy, (Ci-Cs) haloalkoxy, (C 3 -C 8) cycloalkoxy, (C 3 -C 8) cycloalkyl (Ci-C8) - alkoxy, aryloxy, Heteroraryloxy, (Ci-C 8 ) alkoxy (Ci-C 8) alkoxy, (C 2 -C 8) - alkynyl, (Ci-C 8) alkoxy, (C 2 -C 8) alkenyloxy, - bis [(Ci-C 8 ) alkyl] amino- (Ci-C 8) alkoxy, tris - [(Ci-C 8) alkyl] silyl, bis - [(Ci-C 8) alkyl] arylsilyl, bis [(Ci-C 8) alkyl] - (Ci-C8) alkylsilyl, tris - [(Ci-C 8) alkyl] silyl (C 2 -C 8) alkynyl, aryl (C 2 -C 8) alkynyl , heteroaryl (C 2 -C 8) -alkynyl, (Ci-C 8) alkyl (C 2 -C 8) - alkynyl, (C 3 -C 8) cycloalkyl (C 2 -C 8) - alkynyl, (Ci-C 8) haloalkyl (C 2 -C 8) - alkynyl, Heterocyclyl-N- (Ci-C8) alkoxy, nitro, cyano, amino, (Ci-C8) - alkylamino, - bis [(Ci-C 8) alkyl] amino, (Ci-C 8) - alkylcarbonylamino , (C 3 -C 8) -Cycloalkylcarbonylamino, arylcarbonylamino, (dC 8) - alkoxycarbonylamino, heterocyclyl (Ci-C 8) alkoxy, (C 3 -C 8) - cycloalkyl (Ci-Cs) alkyl, ( C 2 -C 8 ) haloalkenyl, (C 2 -C 8 ) haloalkynyl, heterocyclyl (C 2 -C 8 ) alkynyl, (C 3 -C 8 ) -halocycloalkoxy, (C 2 -C 8 ) -haloalkynyloxy , Arylthio, heteroarylthio, (C 1 -C 8) -alkylsulfinyl, (C 1 -C 5) -haloalkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, (C 1 -C 8 ) -alkylsulfonyl, (C 1 -C 8 ) -haloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, thiocyanato, isothiocyanato, (C 3 -C 8) - cycloalkylamino, (C 3 -C 8) -cycloalkyl [(Ci-C 8) alkyl] amino, (C 2 -C 8) - alkenylamino stand,
R1 und R2 mit den Atomen, an die sie gebunden sind, einen vollständig R 1 and R 2 with the atoms to which they are attached, a complete
gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, R2 und R3 mit den Atomen, an die sie gebunden sind, einen vollständig gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden, für Sauerstoff, Schwefel steht, form saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring, R 2 and R 3 with the atoms to which they are attached form a completely saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring, represents oxygen, sulfur,
X für Sauerstoff, Schwefel, N-R4 steht, R4 für Wasserstoff, (Ci-C8)-Alkyl, (C3-C8)-Cycloalkyl, (C3-C8)-Cycloalkyl-X is oxygen, sulfur, NR 4, R 4 represents hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) cycloalkyl
(Ci-C8)-alkyl, (C4-C8)-Cycloalkenyl, Cyano-(d-C8)-alkyl, (C2-C8)-Alkenyl- (d-C8)-alkyl, (Ci-C8)-Haloalkyl, (C2-C8)-Alkinyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)- alkyl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)- Alkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, Arylcarbonyl, (Ci-C 8) alkyl, (C 4 -C 8) cycloalkenyl, cyano (dC 8) alkyl, (C 2 -C 8) alkenyl (dC 8) alkyl, (Ci-C 8 ) -haloalkyl, (C 2 -C 8) alkynyl (Ci-C 8) alkyl, aryl (Ci-C8) - alkyl, heteroaryl (Ci-C 8) alkyl, heterocyclyl (Ci- C 8) alkyl, (Ci-C 8) - alkylcarbonyl, (C3-C8) cycloalkylcarbonyl, arylcarbonyl,
Heteroarylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, Heterocyclylcarbonyl,Heteroarylcarbonyl, (C 1 -C 8 ) -haloalkylcarbonyl, heterocyclylcarbonyl,
Aryl-(Ci-C8)-alkylcarbonyl, (Ci-C8)-Alkoxycarbonyl, (C3-C8)-Cycloalkyl- (Ci-C8)-alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (Ci-C8)- Alkoxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl, (C3-C8)- Cycloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (Ci-C8)- Alkoxycarbonylcarbonyl, Aryl-(Ci-C8)-alkoxycarbonylcarbonyl, (Ci-C8)-Aryl (Ci-C8) alkylcarbonyl, (Ci-C8) alkoxycarbonyl, (C 3 -C 8) cycloalkyl (Ci-C8) alkoxycarbonyl, (C3-C8) -cycloalkoxycarbonyl, (C -C 8) - alkoxycarbonyl, (Ci-C 8) alkyl, (Ci-C8) alkylsulfonyl, (C 3 -C 8) - cycloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (Ci-C 8) - alkoxycarbonylcarbonyl, aryl (C 1 -C 8 ) -alkoxycarbonylcarbonyl, (C 1 -C 8 ) -
Alkylaminothiocarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C3-C8)- Cycloalkylaminocarbonyl, (Ci-C8)-Alkoxy-(d-C8)-alkyl, Bis-[(Ci-C8)- Alkyl]aminocarbonyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C8)- Cycloalkoxycarbonyl-(Ci-C8)-alkyl steht, Alkylaminothiocarbonyl, (Ci-C 8) alkylaminocarbonyl, (C 3 -C 8) - cycloalkylaminocarbonyl, (Ci-C 8) alkoxy (dC 8) alkyl, - bis [(Ci-C 8) - alkyl] aminocarbonyl , aryl, heteroaryl, heterocyclyl, (C 3 -C 8) - cycloalkoxycarbonyl (Ci-C 8) -alkyl,
Q für (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C3-C8)-Cycloalkyl, (C3-C8)-Cycloalkyl- (Ci-Cs)-alkyl, (C4-C8)-Cycloalkenyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, Heteroaryl, Heterocyclyl, Heterocyclylaryl, Heterocyclylheteroaryl, Heteroarylheteroaryl, Heteroarylaryl, Arylaryl, Aryloxyaryl, Aryl-(C2-C8)- alkenyl, Heteroaryl-(C2-C8)-alkenyl, Heterocyclyl-(C2-C8)-alkenyl, Aryl- (C2-C8)-alkinyl, Heteroaryl-(C2-C8)-alkinyl, Heterocyclyl-(Ci-C8)-alkinyl, (C3-C8)-Cycloalkyl-(C2-C8)-alkinyl, (Ci-C8)-Alkylamino-(Ci-C8)-alkyl, Bis- [(Ci-C8)-alkyl]amino-(Ci-C8)-alkyl, Hydroxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy- (Ci-C8)-alkyl, Tris-[(Ci-C8)-alkyl]silyloxy-(Ci-C8)-alkyl, Bis-[(Ci-C8)- alkyl]arylsilyloxy-(Ci-C8)-alkyl, Bis-[(Ci-C8)-alkyl]-(Ci-C8)-alkylsilyloxy- (Ci-C8)-alkyl, Bis-[(Ci-C8)-alkyl]amino-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, Q is (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkyl, ( C 4 -C 8 ) -cycloalkenyl, optionally substituted phenyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl- (C 1 -C 8 ) -alkyl, heteroaryl, heterocyclyl, heterocyclylaryl , Heterocyclylheteroaryl, heteroarylheteroaryl, heteroarylaryl, arylaryl, aryloxyaryl, aryl- (C 2 -C 8 ) -alkenyl, heteroaryl- (C 2 -C 8 ) -alkenyl, heterocyclyl- (C 2 -C 8 ) -alkenyl, aryl- (C 2 -C 4) 8) alkynyl, heteroaryl (C2-C8) alkynyl, heterocyclyl (Ci-C8) -alkynyl, (C 3 -C 8) cycloalkyl (C 2 -C 8) -alkynyl, (Ci- C 8 ) -alkylamino- (C 1 -C 8 ) -alkyl, bis- [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkyl, hydroxy- (C 1 -C 8 ) -alkyl, ( Ci-C 8 ) -alkoxy (Ci-C 8) alkyl, tris - [(Ci-C8) alkyl] silyloxy (Ci-C 8) alkyl, - bis [(Ci-C 8) - alkyl] arylsilyloxy- (Ci-C 8 ) -alkyl, bis - [(Ci-C 8 ) -alkyl] - (Ci-C 8 ) -alkylsilyloxy- (Ci-C 8 ) -alkyl, bis - [(Ci-C 8 ) -alkyl] amino- ( C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl,
(Ci-C8)-Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, Aryloxy-(Ci-C8)-alkyl, Heteroaryloxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, Arylthio- (Ci-C8)-alkyl, Heteroarylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkoxycarbonyl-N- heterocyclyl, Aryl-(Ci-C8)-alkoxycarbonyl-N-heterocyclyl, (d-C8)-Alkyl-N- heterocyclyl, (Ci-Cs)-Alkylsulfonyl-N-heterocyclyl, Arylsulfonyl-N- heterocyclyl, Heteroarylsulfonyl-N-heterocyclyl, (C3-C8)- Cycloalkylsulfonyl-N-heterocyclyl, (Ci-C8)-Haloalkylsulfonyl-N- heterocyclyl, (Ci-C8)-Alkylcarbonyl-N-heterocyclyl, Arylcarbonyl-N- heterocyclyl, Heteroarylcarbonyl-N-heterocyclyl, (C3-C8)- Cycloalkylcarbonyl-N-heterocyclyl, (Ci-C8)-Cycloalkyl-N-heterocyclyl, Aryl-N-heterocyclyl, Aryl-(Ci-C8)-alkyl-N-heterocyclyl, Bis-[(Ci-C8)- alkyl]aminoalkyl-N-heterocyclyl, Bis-[(Ci-C8)-alkyl]aminosulfonyl-N- heterocyclyl, Heteroaryloxyaryl, Heteroaryloxyheteroaryl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, aryloxy- (C 1 -C 8 ) -alkyl, heteroaryloxy- (C 1 -C 8 ) -alkyl, ( C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl, arylthio (C 1 -C 8 ) -alkyl, heteroarylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxycarbonyl-N- heterocyclyl, aryl (Ci-C8) alkoxycarbonyl-N-heterocyclyl, (dC 8) alkyl-N-heterocyclyl, (Ci-Cs) alkylsulphonyl-N-heterocyclyl, arylsulfonyl-N-heterocyclyl, heteroarylsulfonyl-N- heterocyclyl, (C 3 -C 8) - cycloalkylsulfonyl-N-heterocyclyl, (Ci-C 8) haloalkylsulfonyl-N- heterocyclyl, (Ci-C 8) alkylcarbonyl-N-heterocyclyl, arylcarbonyl-N-heterocyclyl, heteroarylcarbonyl N-heterocyclyl, (C 3 -C 8) - cycloalkyl carbonyl-N-heterocyclyl, (Ci-C 8) -cycloalkyl-N-heterocyclyl, N-heterocyclyl-aryl, aryl (Ci-C8) alkyl-N- heterocyclyl, bis - [(C 1 -C 8 ) -alkyl] aminoalkyl-N-heterocyclyl, bis - [(C 1 -C 8 ) -alkyl] aminosulfonyl-N-heterocyclyl, heteroaryloxyaryl, heteroaryloxyheteroaryl,
AryloxyheteroaryS, (Ci-C8)-Alkylsulfinyl, (Ci-C8)-Alkylthio, (Ci-C8)- Alkylsulfonyl, (C3-C8)-Cycloalkylsulfinyl, (C3-C8)-Cycloalkylthio, (C3-C8)- Cycloalkylsulfonyl, Arylsulfinyl, Arylthio, Arylsulfonyl, Amino, (Ci-C8)- Alkylamino, Bis-[(Ci-C8)-Alkyl]amino, Arylamino, Aryl-(Ci-C8)-a!kylamino, (C3-C8)-Cycloalkylamino, Formyl, (Ci-C8)-Alkylcarbonyl, Arylcarbonyl, lmino-(Ci-C8)-alkyl, (Ci-C8)-Alkylimino-(Ci-C8)-alkyl, Arylimino-(Ci-C8)- alkyl, (Ci-C8)-Alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (C3-C8)- Cycloalkyl-(Ci-C8)-alkoxycarbonyl, Aryl-(Ci-C8)-alkoxycarbonyl, Aryl- (Ci-C8)-alkylaminocarbonyl, Aminocarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C3-C8)-Cycloalkylaminocarbonyl, Bis-[(Ci-C8)-alkyl]aminocarbonyl, Heterocyclyl-N-carbonyl, Imino, (Ci-C8)-Alkylimino, Arylimino, (C3-C8)- Cycloalkylimino, (C3-C8)-Cycloalkyl-(Ci-C8)-alkylimino, Hydroxyimino, (Ci-C8)-Alkoxyimino, (C2-C8)-Alkenyloxyimino, (C3-C8)-Cycloalkoxyimino, (C3-C8)-Cyloalkyl-(CrC8)-alkoxyimino, Aryloxyimino, Aryl-(Ci-Cs)- alkoxyimino, Heteroaryl-(Ci-C8)-alkoxyimino, Heteroaryloxyimino, Heteroarylimino, Heterocyclylimino, Heterocyclyl-(Ci-C8)-alkylimino, Aminoimino, (Ci-Cs)-Alkylaminoimino, Arylaminoimino, AryloxyheteroaryS, (Ci-C8) alkylsulfinyl, (Ci-C8) alkylthio, (Ci-C 8) - alkylsulfonyl, (C 3 -C 8) cycloalkylsulfinyl, (C 3 -C 8) -cycloalkylthio, ( C 3 -C 8) - cycloalkylsulfonyl, arylsulfinyl, arylthio, arylsulfonyl, amino, (Ci-C8) - alkylamino, - bis [(Ci-C 8) -alkyl] amino, arylamino, aryl- (Ci-C 8) -a alkylamino, (C 3 -C 8) cycloalkylamino, formyl, (Ci-C 8) alkylcarbonyl, arylcarbonyl!, imino (Ci-C 8) alkyl, (Ci-C 8) -alkylimino (C -C 8) alkyl, Arylimino- (Ci-C 8) - alkyl, (Ci-C8) alkoxycarbonyl, (C 3 -C 8) -cycloalkoxycarbonyl, (C 3 -C 8) - cycloalkyl (Ci- C8) alkoxycarbonyl, aryl (Ci-C8) alkoxycarbonyl, aryl (Ci-C8) alkylaminocarbonyl, aminocarbonyl, (Ci-C 8) alkylaminocarbonyl, (C 3 -C 8) cycloalkylaminocarbonyl, bis - [(Ci-C 8) alkyl] aminocarbonyl, heterocyclyl-N-carbonyl, imino, (Ci-C 8) alkylimino, arylimino, (C 3 -C 8) - Cycloalkylimino, (C 3 -C 8) - cycloalkyl- (Ci-C 8) alkylimino, hydroxyimino, (Ci-C 8) alkoxyimino, (C2-C8) -Alkenyloxyimino, (C 3 -C 8) -Cycloal koxyimino, (C 3 -C 8) -Cyloalkyl- (CRC 8) alkoxyimino, aryloxyimino, aryl (Ci-Cs) - alkoxyimino, heteroaryl (Ci-C 8) alkoxyimino, Heteroaryloxyimino, Heteroarylimino, Heterocyclylimino, heterocyclyl (C 1 -C 8 ) -alkylimino, aminoimino, (C 1 -C 8 ) -alkylaminoimino, arylaminoimino,
Heteroarylaminoimino, (C3-C8)-Cycloalkylaminoimino, Bis-[(d-C8)- Alkyljaminoimino, Aryl-(Ci-C8)-alkylaminoimino, Aryl[(Ci-C-8)- alkyljaminoimino, (C3-C8)-Cycloalkyl[(Ci-C8)-alkyl]aminoimino, (C3-Ce)- Cycloalkyl-(Ci-C8)-alkylaminoimino, Heterocyclylaminoimino, Heteroaryl- (Ci-C8)-alkoxy-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, Heteroarylaminoimino, (C 3 -C 8 ) -cycloalkylaminoimino, bis - [(dC 8 ) - Alkylaminoimino, aryl- (C 1 -C 8) -alkylaminoimino, aryl [(C 1 -C 8) -alkylaminoimino, (C 3 -C 8) -cycloalkyl [(C 1 -C 8) -alkyl] aminoimino, (C 3 -Ce) -cycloalkyl (C 1 -C 8 ) -alkylaminoimino, heterocyclylaminoimino, heteroaryl- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl,
Heterocyclyl-N-(Ci-C8)-alkyl, Aryl-[(Ci-C8)-alkyl]amino-(Ci-C8)-alkyl, Aryl- (Ci-C8)-alkyl[(Ci-C8)-alkyl]amino-(Ci-C8)-alkyl, (Ci-C8)-Alkoxycarbonyi- (Ci-C8)-alkylamino-(Ci-C8)-a!kyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)- alkyl[(Ci-C8)-alkyl]amino-(Ci-C8)-alkyl, Heteroaryl-[(Ci-C8)-alkyl]amino- (Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkyS-[(Ci-C8)-alkyl]amino-(Ci-C8)-alkyl, - (C3-C8)-Cycloalkyl-[(Ci-C8)-alkyl]amino-(Ci-C8)-alkyl, (C3-C8)- Cycloalkylamino-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkoxy-(Ci-C8)-alkylaryl, Heterocyclyl-N-(Ci-C8)-alkylaryl, Aryl[(Ci-C8)-alkyl]amino-(Ci-C8)- alkylaryl, Aryl-(Ci-C8)-alkyl[(Ci-C8)-alkyl]amino-(Ci-C8)-alkylaryl, (Ci-Ce)- Alkoxycarbonyl-(Ci-C8)-alkylamino-(Ci-C8)-alkylaryl, (Ci-Cs)- Alkoxycarbonyl-(Ci-C8)-alkyl[(Ci-C8)-alkyl]amino-(Ci-C8)-alkylaryl, Heteroaryl[(Ci-C8)-alkyl]amino-(Ci-C8)-alkylaryl, Heteroaryl-(Ci-C8)- alkyl[(Ci-C8)-alkyl]amino-(Ci-C8)-alkylaryl, (C3-C8)-Cycloalkyl[(Ci-C8)- alkyl]amino-(Ci-C8)-alkylaryl, (C3-C8)-Cycloalkylamino-(Ci-C8)-alkylaryl, (Ci-C8)-Alkoxy[(Ci-C8)-alkoxy]-(Ci-C8)-alkylaryl sieht, zusätzlich, wenn X für ein Sauerstoffatom oder X für ein Schwefelatom steht, für (Ci-C8)-Haloalkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, (C3-C8)- Halocycloalkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-haloalkyl, Aryl-(Ci-C8)- haloalkyl, (Ci-C8)-Alkylthio-(Ci-C8)-haloalkyl, Bis[(Ci-C8)-alkyl]amino- (Ci-C8)-alkoxy-(Ci-C8)-haloalkyl steht, für Wasserstoff, Hydroxy, (Ci-C8)-Alkyl, (C3-C8)-Cycloalkyl, (C3-C8)- Halocycloalkyl, Halogen, (C2-C8)-Alkenyl-(Ci-C8)-alkyl, (Ci-C8)-Haloalkyl, (C-2-C8)-Alkinyl, (C2-C8)-Alkenyl, Cyano-(Ci-C8)-alkyl, Nitro-(Ci-C8)-alkyl, Amino-(Ci-C8)-alkyl, Alkyl-(Ci-C8)-amino-(Ci-C8)-alkyl, Bis-[(Ci-C8)- Alkyl]amino-(Ci-C8)-alkyl, (C2-C8)-Alkinyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-CeJ-Alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (Ci-Ce)- Alkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, (Ci-C8)-Alkylsu!finyl, Arylsulfinyl, (C3-C8)-Cyc!oalkylsu!finyl, (Ci-C8)- Alkoxycarbonyl-(Ci-C8)-alkyl, Aryl, HeteroaryS, Heterocyclyl, Aminocarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylaminocarbonyl-(Ci-C8)-alkyl,Heterocyclyl-N- (C 1 -C 8 ) -alkyl, aryl - [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkyl [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxycarbonyi (C 1 -C 8 ) -alkylamino- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxycarbonyl - (Ci-C 8) - alkyl [(Ci-C8) alkyl] amino- (Ci-C 8) alkyl, heteroaryl - [(Ci-C 8) alkyl] amino- (Ci-C 8) - alkyl, heteroaryl- (C 1 -C 8) -alkyS - [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkyl, - (C 3 -C 8) -cycloalkyl - [(C 1 -C 8 ) -alkyl ] amino- (Ci-C 8) alkyl, (C 3 -C 8) - cycloalkylamino (Ci-C 8) alkyl, aryl (Ci-C8) alkoxy (Ci-C8) alkylaryl, Heterocyclyl-N- (C 1 -C 8 ) -alkylaryl, aryl [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkylaryl, aryl- (C 1 -C 8 ) -alkyl [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkylaryl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 8 ) -alkylamino- (C 1 -C 8 ) -alkylaryl, (C 1 -C 8 ) -alkoxycarbonyl- (C 1 -C 4 -alkyl) 8 ) -alkyl [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8) -alkylaryl, heteroaryl [(C 1 -C 8) -alkyl] amino- (C 1 -C 8) -alkylaryl, heteroaryl- (C 1 -C 8) - alkyl [(Ci-C8) alkyl] amino- (Ci-C8) alkylaryl, (C3-C8) -cycloalkyl [(Ci-C 8) - alkyl] amino- (Ci-C8) alkylaryl , (C 3 -C 8 ) -cycloalkylamino- (C 1 -C 8 ) -alkylaryl, (C 1 -C 8 ) -alkoxy [(C 1 -C 8 ) -alkoxy] - (C 1 -C 8 ) -alkylaryl, additionally when X is a Oxygen atom or X is a sulfur atom, for (Ci-C 8 ) -haloalkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -haloalkyl, (C 3 -C 8 ) -halocycloalkyl, (Ci-C 8 ) -haloalkoxy- (C 1 -C 8 ) -haloalkyl, aryl- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -haloalkyl, bis [(C 1 -C 8 ) alkyl] amino- (Ci-C 8) alkoxy (Ci-C 8) haloalkyl, hydrogen, hydroxy, (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl, ( C 3 -C 8) - halocycloalkyl, halogen, (C2-C8) alkenyl (Ci-C 8) alkyl, (Ci-C 8) haloalkyl, (C2-C8) -alkynyl, ( C 2 -C 8) alkenyl, cyano (Ci-C 8) alkyl, nitro, (Ci-C 8) alkyl, amino (Ci-C 8) alkyl, alkyl (Ci-C 8) amino- (Ci-C 8) alkyl, - bis [(Ci-C 8) - alkyl] amino- (Ci-C 8) alkyl, (C2-C8) alkynyl (Ci-C 8) alkyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, (C 1 -C 8 ) -alkyl Alkoxycarbonyl, (C 3 -C 8) -cycloalkoxyca rbonyl, (C 1 -C 6) -alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C 3 -C 8) -cycloalkylsulfonyl, (C 1 -C 8 ) -alkylsulphonyl, arylsulfinyl, (C 3 -C 8 ) -cycloalkylsilyl, (C 1 -C 8 ) -alkoxycarbonyl- (C 1 -C 8 ) -alkyl, aryl, heteroaryS, heterocyclyl, aminocarbonyl (C 1 -C 8) -alkyl, (C 1 -C 8) -alkylaminocarbonyl- (C 1 -C 8) -alkyl,
Bis-[(Ci-C8)-alkyl]aminocarbonyl-(Ci-C8)-alkyl, (C3-C8)- Cycloalkylaminocarbonyl-(Ci-C8)-alkyl, Hydroxycarbonyl-(Ci-C8)-alkyl, Amino, (Ci-C8)-A!ky!amino, Arylamino, (Ci-C8)-Alkoxy steht und Z2 für Wasserstoff, (Ci-C8)-Alkyl, (C3-C8)-Cycloalkyl, (Ci-Cs)-HaloaSkyl,Bis - [(C 1 -C 8 ) -alkyl] aminocarbonyl- (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkylaminocarbonyl- (C 1 -C 8 ) -alkyl, hydroxycarbonyl- (C 1 -C 8 ) - alkyl, amino, (Ci-C 8) -A! ky! amino, arylamino, (Ci-C8) -alkoxy and Z 2 is hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) -Cycloalkyl, (Ci-Cs) -HaloaSkyl,
(C2-C8)-Alkinyl, (C2-C8)-Alkenyl, Cyano-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkyl,(C 2 -C 8) -alkynyl, (C 2 -C 8) alkenyl, cyano (Ci-C 8) alkyl, aryl (Ci-C8) alkyl,
Heteroaryl-(Ci-C8)-alkyl, (Ci-Cs)-A!kylcarbonyl, (Ci-C8)-A!koxycarbonyl steht oder Heteroaryl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, (C 1 -C 8 ) -alkoxycarbonyl or
Z1 und Z2 zusammen mit dem Atomen, an das sie gebunden sind, einen Z 1 and Z 2 together with the atom to which they are attached, one
vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden oder  form fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring or
Z1 und Z2 zusammen eine N-(Bis-(Ci-C8)-alkyl)sulfanyliden-, N-(Aryl-(Ci-C8)- alkyl)sulfanyliden-, N-(Bis-(C3-C8)-Cycloalkyl)sulfanyliden-, N-((Ci-Ce)-Z 1 and Z 2 together form a N- (bis (Ci-C8) alkyl) sulfanyliden-, N- (aryl (Ci-C 8) - alkyl) sulfanyliden-, N- (bis- (C 3 - C 8 ) cycloalkyl) sulfanylidene, N - ((Ci-Ce) -
Alkyl-(C3-C8)-cycloalkyl)sulfanylidengruppe oder eine N,N-di-(Ci-C8)- alkylformylidengruppe bilden. Alkyl (C 3 -C 8 ) cycloalkyl) sulfanylidene group or an N, N-di- (C 1 -C 8 ) -alkylformylidene group.
3. Verwendung gemäß Anspruch 1 , wobei in Formel (I) 3. Use according to claim 1, wherein in formula (I)
R1, R2, R3 unabhängig voneinander für Wasserstoff, lod, Brom, Chlor, Fluor, (d-C )-Alkyl, (C3-C )-Cycloalkyl, (C4-C )-Cycloalkenyl, (C3-C7)- Halocycloalkyl, (C2-C )-Alkenyl, (C2-C/)-Alkinyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C7)-alkyl, Aryl-(C2-C7)-alkenyl, Heteroaryl,R 1 , R 2 , R 3 independently of one another represent hydrogen, iodine, bromine, chlorine, fluorine, (C 1 -C 4 ) -alkyl, (C 3 -C 6) -cycloalkyl, (C 4 -C) -cycloalkenyl, (C 3 -C 7) - Halocycloalkyl, (C2-C) alkenyl, (C2-C /) - alkynyl, optionally substituted phenyl, aryl- (C 1 -C 7) -alkyl, aryl- (C 2 -C 7) -alkenyl, heteroaryl,
Heteroaryl-(Ci-C7)-alkyl, Heterocyciyl, Heterocyclyl-(Ci-C7)-alkyl, (C1-C7)- Alkoxy-(Ci-C7)-a!kyl, (Ci-C7)-Alkylthio, (Ci-C7)-Haloalkylthio, (C1-C7)- Haloalkyl, (Ci-C7)-Alkoxy, (Ci-C7)-Haloa!koxy! (C3-C7)-Cycloalkoxy, Heteroaryl- (Ci-C7) alkyl, Heterocyciyl, heterocyclyl (Ci-C7) alkyl, (C1-C7) - alkoxy (Ci-C 7) -a alkyl, (Ci-C 7)! - alkylthio, (Ci-C 7) haloalkylthio, (C1-C7) - haloalkyl, (Ci-C7) alkoxy, (Ci-C7) -alkoxy -Haloa! (C 3 -C 7 ) -cycloalkoxy,
(C3-C/)-Cycloaikyl-(Ci-C7)-aikoxy, Aryloxy, Heteroraryloxy, (C1-C7)- (C3-C /) - cycloalkyl (Ci-C7) -aikoxy, aryloxy, heteroaryloxy, (C1-C7) -
Alkoxy-(Ci-C/)-aikoxy, (C2-C7)-Alkinyi-(Ci-C7)-alkoxy, (C2-C7)-Alkenyloxy, Bis-[(Ci-C7)-alkyl]amino-(Ci-C7)-aikoxy, Tris-[(Ci-C/)-alky!]si!yl, Bis- [(Ci-C7)-alkyl]arylsiiyl, Bis-[(Ci-C/)-alkyl]-(Ci-C/)-alkylsilyl, Tris-[(Ci-C7)- a!kyl]si!yl-(C2-C/)-alkinyl, Aryl-(C2-C7)-alkinyl, Heteroaryl-(C2-C7)-alkinyl, (Ci-C7)-Aikyl-(C2-C7)-alkinyl, (C3-C7)-Cycioalkyl-(C2-C7)-alkinyl, (C1-C7)-Alkoxy- (C 1 -C 4 ) -alkoxy, (C 2 -C 7 ) -alkyno (C 1 -C 7 ) -alkoxy, (C 2 -C 7 ) -alkenyloxy, bis - [(C 1 -C 7 ) -alkyl] -amino (Ci-C7) -aikoxy, tris - [(Ci-C /) -alkyl] si! Yl, bis [(Ci-C7) -alkyl] arylsilyl, bis - [(Ci-C /) -alkyl] - (Ci-C /) -alkylsilyl, tris - [(Ci-C 7 ) -alkyl] si! Yl- (C 2 -C /) -alkynyl, aryl- (C 2 -C 7 ) -alkynyl, heteroaryl - (C 2 -C 7 ) -alkynyl, (C 1 -C 7 ) -alkyl (C 2 -C 7 ) -alkynyl, (C 3 -C 7 ) -cycloalkyl- (C 2 -C 7 ) -alkynyl, (C 1 -C 7 ) -
Haloalkyl-(C2-C7)-alkinyl, Heterocyclyl-N-(Ci-C7)-a!koxy, Nitro, Cyano, Amino, (Ci-C7)-Alkylamino, Bis-[(Ci-C7)-alkyl]amino, (C1-C7)- Alkylcarbonylamino, (C3-C/)-Cycloalkyicarbonyiamino, Haloalkyl- (C 2 -C 7 ) -alkynyl, heterocyclyl-N- (C 1 -C 7 ) -alkoxy, nitro, cyano, amino, (C 1 -C 7 ) -alkylamino, bis - [(C 1 -C 7) -alkyl ] amino, (C1-C7) -alkylcarbonylamino, (C3-C /) -cycloalkyicarbonyiamino,
AryScarbonylamino, (Ci-C7)-Alkoxycarbonylamino, Heterocyclyl-(Ci-C7)- alkoxy, (C3-C7)- Cycloalkyl-(Ci-C7)-alkyl, (C2-C7)-Haloa!kenyl, (C2-C7)-Arylcarbonylamino, (C 1 -C 7) -alkoxycarbonylamino, heterocyclyl- (C 1 -C 7 ) -alkoxy, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkyl, (C 2 -C 7 ) -haloalkylene, (C2 C7) -
Haloalkinyl, Heterocyclyl-(C2-C7)-alkinyl, (C3-C7)-Halocycloalkoxy, Haloalkynyl, heterocyclyl (C 2 -C 7) -alkynyl, (C 3 -C 7) -halocycloalkoxy,
(C2-C7)-Haloalkinyloxy, Arylthio, Heteroarylthio, (Ci-C7)-Alkylsulfinyl, (Ci-C7)-Haloalkyisulfinyl, Arylsulfinyl, Heteroarylsulfinyi, (C1-C7)- Alkylsulfonyl, (Ci-C7)-Haloalkylsulfonyl, Arylsuifonyl, Heteroaryisulfonyl, Thiocyanato, Isothiocyanato, (C3-C/)-Cycloalkylamino, (C3-C7)- (C 2 -C 7) -haloalkynyloxy, arylthio, heteroarylthio, (C 1 -C 7) -alkylsulfinyl, (C 1 -C 7) -haloalkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, (C 1 -C 7) -alkylsulfonyl, (C 1 -C 7) -haloalkylsulfonyl, arylsulfonyl, Heteroaryisulfonyl, thiocyanato, isothiocyanato, (C3-C /) -cycloalkylamino, (C3-C7) -
Cycloalkyl[(Ci-C7)-alkyl]amino, (C2-C7)-Alkenylamino stehen, Cycloalkyl [(C 1 -C 7) -alkyl] amino, (C 2 -C 7) -alkenylamino,
R1 und R2 mit den Atomen, an die sie gebunden sind, einen vollständig R 1 and R 2 with the atoms to which they are attached, a complete
gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden,  form saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring,
R2 und R3 mit den Atomen, an die sie gebunden sind, einen vollständig R 2 and R 3 with the atoms to which they are attached, a complete
gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden,  form saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring,
W für Sauerstoff, Schwefel steht, für Sauerstoff, Schwefe!, N-R4 steht, für Wasserstoff, (Ci-C7)-A!kyl, (C3-C7)-Cycloa!kyl, (C3-C7)-Cycloalkyl- (d-C/)-alkyl, (C4-C7)-Cycloalkenyl, Cyano-(Ci-C7)-alkyl, (C2-C )-Alkenyl- (Ci-C/)-alkyl, (Ci-C7)-Haloalkyl, (C2-C7)-Alkinyl-(Ci-C7)-a!kyl, Aryl-(Ci-C7)- alkyl, Heteroaryl-(Ci-C7)-alkyl, Heterocycly!-(Ci-C7)-alkyl, (C1-C7)- Alkylcarbonyl, (C3-C )-Cycloalkylcarbonyl, Arylcarbonyl, W stands for oxygen, sulfur, represents oxygen, sulfur !, NR 4, represents hydrogen, (Ci-C 7) -A -alkyl, (C3-C 7) -Cycloa alkyl, (C 3 -C 7) cycloalkyl (dC /)! - alkyl, (C 4 -C 7 ) -cycloalkenyl, cyano- (C 1 -C 7 ) -alkyl, (C 2 -C) -alkenyl- (C 1 -C 6 ) -alkyl, (C 1 -C 7 ) -haloalkyl, (C 2 -C 7) alkynyl (C 7) -a alkyl, aryl (Ci-C7) - alkyl, heteroaryl (Ci-C7) alkyl, heterocyclyl - (Ci-C 7 ) -alkyl, (C 1 -C 7 ) -alkylcarbonyl, (C 3 -C 4) -cycloalkylcarbonyl, arylcarbonyl,
Heteroarylcarbonyl, (Ci-C )-Haloalkylcarbonyl, Heterocyclylcarbonyl, Aryl-(Ci-C/)-alkylcarbonyl, (Ci-C7)-Alkoxycarbonyl, (C3-C/)-Cycloalkyl- (Ci-C )-alkoxycarbonyl, (C3-C )-Cycloalkoxycarbonyl, (C1-C7)- Alkoxycarbonyl-(Ci-C/)-alkyl, (Ci-C/)-Alkylsulfonyl, (C3-C7)- Cycloalkylsulfonyl, Ary!sulfonyl, Heteroarylsulfonyl, (C1-C7)- Alkoxycarbonylcarbonyl, Aryl-(Ci-C/)-alkoxycarbonylcarbonyl, (Ci-C7)- Aikylaminothiocarbonyl, (Ci-C/J-Alkylaminocarbonyl, (C3-C7)- Cycloalkylaminocarbonyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Bis-[(Ci-C/)- A!kyljaminocarbonyl, Aryl, Heteroaryl, Heterocyclyl, (C3-C7)- Cycloalkoxycarbonyl-(Ci-C )-alkyl steht, für (Ci-C7)-Alkyl, (C2-C/)-Alkenyl, (C3-C7)-CycSoaSkyl, (C3-C7)-Cycloalkyl- (Ci-C7)-alkyl, (C4-C )-Cycloalkenyl, gegebenenfalls substituiertes Phenyl, Aryl-(Ci-C/)-alkyl, Heteroaryl-(Ci-C7)-alkyl, Heterocyclyl-(Ci-C )-alkyl,Heteroarylcarbonyl, (Ci-C) -haloalkylcarbonyl, heterocyclylcarbonyl, aryl- (Ci-C /) - alkylcarbonyl, (Ci-C 7 ) -alkoxycarbonyl, (C 3 -C /) -cycloalkyl- (Ci-C) -alkoxycarbonyl, (C3-C) -cycloalkoxycarbonyl, (C1-C7) -alkoxycarbonyl- (Ci-C /) -alkyl, (Ci-C /) -alkylsulfonyl, (C3-C7) -cycloalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C1 -C7) - alkoxycarbonylcarbonyl, aryl- (Ci-C /) - alkoxycarbonylcarbonyl, (Ci-C 7 ) - Aikylaminothiocarbonyl, (Ci-C / J-alkylaminocarbonyl, (C3-C7) - cycloalkylaminocarbonyl, (Ci-C 7 ) - Alkoxy- (C 1 -C 7 ) -alkyl, bis - [(C 1 -C 4 ) -alkyl] -aminocarbonyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkoxycarbonyl- (C 1 -C 4) -alkyl, C 1 -C 7 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 3 -C 7 ) -CycSoaSkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkyl, (C 4 -C 4) - Cycloalkenyl, optionally substituted phenyl, aryl- (C 1 -C 6) -alkyl, heteroaryl- (C 1 -C 7 ) -alkyl, heterocyclyl- (C 1 -C 4) -alkyl,
Heteroaryl, Heterocyclyl, Heterocyclylaryl, Heterocyclylheteroaryl, Heteroarylheteroaryl, Heteroarylaryl, Arylaryl, Aryloxyaryl, Aryl-(C2-C )- alkenyl, Heteroaryl-(C2-C7)-alkenyl, Heterocyclyl-(C2-C )-alkenyl, Aryl- (C2-C/)-alkinyl, Heteroaryl-(C2-C/)-alkinyl, Heterocyclyl-(Ci-C7)-alkinyl, (C3-C7)-Cycloalkyl-(C2-C7)-alkinyl, (Ci-C7)-Alkylamino-(Ci-C7)-alkyl, Bis- [(Ci-C7)-alkyl]amino-(Ci-C7)-alkyl, Hydroxy-(Ci-C7)-alkyl, (Ci-Cz)-Alkoxy- (Ci-C7)-alkyl, Tris-[(Ci-C7)-alkyl]silyloxy-(Ci-C7)-alkyl, Bis-[(Ci-C7)- alkyl]arylsilyloxy-(Ci-C7)-alkyl, Bis-[(Ci-C7)-alkyl]-(Ci-C7)-alkylsilyloxy- (Ci-C7)-alkyl, Bis-[(Ci-C )-alkyl]amino-(Ci-C7)-alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C/)-alkoxy-(Ci-C/)-alkyl, Aryloxy-(Ci-C/)-alkyl, Heteroaryloxy-(Ci-C/)-alkyl, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, Arylthio- (Ci-C7)-alkyl, Heteroarylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkoxycarbonyl-N- heterocyclyl, Aryl-(Ci-C )-alkoxycarbonyl-N-heterocyclyl, (Ci-C/J-Alkyl-N- heterocyclyl, (Ci-CzJ-Alkylsulfonyl-N-heterocyclyl, Arylsu!fonyl-N- heterocyclyl, Heteroarylsulfonyl-N-heterocyclyl, (C3-C7)- Cycloalkylsu!fonyl-N-heterocyc!yl, (Ci-C/)-Haloalkylsulfonyl-N- heterocyclyl, (Ci-C/J-Alkylcarbonyl-N-heterocyclyl, Arylcarbonyl-N- heterocyclyl, Heteroarylcarbonyl-N-heterocycly!, (C3-C7)- Cycloalkylcarbonyl-N-heterocyclyl, (Ci-C/)-Cycloalkyl-N-heterocyc!yl, Aryl-N-heterocyclyl, Aryl-(Ci-C7)-alkyl-N-heterocyc!yl, Bis-[(Ci-C7)- alkyl]aminoalkyl-N-heterocyclyl, Bis-[(Ci-C/)-alkyl]aminosulfony!-N- heterocyclyl, Heteroaryloxyaryl, Heteroaryloxyheteroaryl, Heteroaryl, heterocyclyl, heterocyclylaryl, heterocyclylheteroaryl, Heteroarylheteroaryl, Heteroarylaryl, arylaryl, aryloxyaryl, aryl (C2-C) - alkenyl, heteroaryl (C2-C7) alkenyl, heterocyclyl (C2-C) alkenyl, aryl ( C 2 -C /) - alkynyl, heteroaryl (C 2 -C /) - alkynyl, heterocyclyl (Ci-C7) alkynyl, (C 3 -C 7) cycloalkyl (C2-C7) alkynyl, (C 1 -C 7 ) -alkylamino- (C 1 -C 7 ) -alkyl, bis- [(C 1 -C 7 ) -alkyl] amino- (C 1 -C 7 ) -alkyl, hydroxy- (C 1 -C 7 ) -alkyl, (C 1 -C 6) -alkoxy- (C 1 -C 7 ) -alkyl, tris - [(C 1 -C 7 ) -alkyl] silyloxy- (C 1 -C 7 ) -alkyl, bis - [(C 1 -C 7 ) - alkyl] arylsilyloxy- (Ci-C 7 ) -alkyl, bis - [(Ci-C7) -alkyl] - (Ci-C 7 ) -alkylsilyloxy- (Ci-C 7 ) -alkyl, bis - [(Ci-C ) -alkyl] amino- (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 4 ) -alkoxy- (C 1 -C 6) -alkyl, Aryloxy- (C 1 -C 6 ) -alkyl, heteroaryloxy- (C 1 -C 6 ) -alkyl, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, arylthio (C 1 -C 7 ) -alkyl , Heteroarylthio (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxycarbonyl-N-heterocyclyl, aryl- (C 1 -C 4) -alkoxycarbonyl-N-heterocyclyl, (C 1 -C 5 -alkyl-N-) heterocyclyl, (C 1 -C 6 -alkylsulfonyl-N-heterocyclyl, arylsulfonyl-N-heterocyclyl, heteroarylsulfonyl-N-heterocyclyl, (C 3 -C 7) -cycloalkylsulfonyl-N-heterocyclyl, (C 1 -C 4) - Haloalkylsulfonyl-N-heterocyclyl, (C 1 -C 5 -alkylcarbonyl-N-heterocyclyl, arylcarbonyl-N-heterocyclyl, heteroarylcarbonyl-N-heterocyclyl, (C 3 -C 7) -cycloalkylcarbonyl-N-heterocyclyl, (C 1 -C 4) -Cycloalkyl-N-heterocyclyl, aryl-N-heterocyclyl, aryl- (C 1 -C 7 ) -alkyl-N-heterocyclyl, bis - [(C 1 -C 7 ) -alkyl] -aminoalkyl-N-heterocyclyl, Bis - [(Ci-C /) -alkyl] aminosulfony! -N-heterocyclyl, heteroaryloxyaryl, heteroaryloxyheteroaryl,
Aryloxyheteroaryl, (Ci-C7)-Alkylsu!finyl, (Ci-C/)-Alkylthio, (C1-C7)- Alkylsulfonyl, (C3-C7)-CycSoalkylsulfinyi, (C3-C7)-Cycloalkylthio, (C3-C7)- Cycloalkylsulfonyl, Arylsulfinyl, Arylthio, Arylsulfonyl, Amino, (C1-C7)- Alkylamino, Bis-[(Ci-C7)-Alkyl]amino, Arylamino, Aryl-(Ci-C7)-alkylamino, (C3-C7)-Cycloalkylamino, Formyl, (Ci-C7)-Alkylcarbonyl, Arylcarbonyl, lmino-(Ci-C7)-alkyl, (Ci-C7)-Alkylimino-(Ci-C7)-alkyl, Arylimino-(Ci-C7)- alkyl, (Ci-C7)-Alkoxycarbonyl, (C3-C7)-Cycloalkoxycarbonyl, (C3-C7)- Cycloalkyl-(Ci-C7)-alkoxycarbonyl, Aryl-(Ci-C7)-alkoxycarbonyl, Aryl- (Ci-C7)-alkylaminocarbonyl, Aminocarbonyl, (Ci-C7)-Alkylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl, Bis-[(Ci-C7)-a!kyl]aminocarbonyl, Heterocyclyl-N-carbonyl, Imino, (Ci-C7)-Alkylimino, Arylimino, (C3-C7)- Cycloalkylimino, (C3-C7)-Cycloalkyl-(Ci-C7)-a!kylimino, Hydroxyimino, (Ci-C7)-Alkoxyimino, (C2-C7)-ASkenyloxyimino, (C3-C7)-Cycloalkoxyimino, (C3-C7)-CyloaSkyl-(Ci-C7)-alkoxyimino, Aryloxyimino, Aryl-(Ci-C7)- alkoxyimino, Heteroaryl-(CrC7)-alkoxyimino, Heteroaryloxyimino, Heteroarylimino, Heterocyclylimino, Heterocyclyl-(Ci-C7)-alkylimino, Aminoimino, (Ci-C7)-Alkylaminoimino, Arylaminoimino, Aryloxyheteroaryl, (Ci-C 7) -Alkylsu finyl, (Ci-C /) - alkylthio, (C1-C7) - alkylsulfonyl, (C3-C 7) -CycSoalkylsulfinyi, (C 3 -C 7) cycloalkylthio, ( C3-C7) -cycloalkylsulfonyl, arylsulfinyl, arylthio, arylsulfonyl, amino, (C1-C7) -alkylamino, bis- [(Ci-C7) -alkyl] -amino, arylamino, aryl- (Ci-C7) -alkylamino, (C3 -C 7) -cycloalkylamino, formyl, (C 1 -C 7 ) -alkylcarbonyl, arylcarbonyl, imino (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylimino (C 1 -C 7 ) -alkyl, arylimino (C 1 -C 4 ) -alkyl, C 7 ) -alkyl, (C 1 -C 7 ) -alkoxycarbonyl, (C 3 -C 7 ) -cycloalkoxycarbonyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7) -alkoxycarbonyl, aryl- (C 1 -C 7) -alkoxycarbonyl, aryl- (C 1 -C 7) -alkylaminocarbonyl, aminocarbonyl, (C 1 -C 7) -alkylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl, bis [(C 1 -C 7) -alkyl] aminocarbonyl, heterocyclyl-N-carbonyl, imino, ( C 1 -C 7) -alkylimino, arylimino, (C 3 -C 7) -cycloalkylimino, (C 3 -C 7) -cycloalkyl- (C 1 -C 7) -alkylamino, hydroxyimino, (C 1 -C 7) -alkoxyimino, (C 2 -C 7) -Askenyloxyimino, (C3-C7) -cycloalkoxyimino, (C3-C7) -cycloalkyl- (Ci-C7) -alkoxyimino, aryloxyimino, aryl- ( C 1 -C 7) -alkoxyimino, heteroaryl- (C 1 -C 7) -alkoxyimino, heteroaryloxyimino, heteroarylimino, heterocyclylimino, heterocyclyl- (C 1 -C 7) -alkylimino, aminoimino, (C 1 -C 7) -alkylaminoimino, arylaminoimino,
Heteroarylaminoimino, (C3-C7)-Cycloalkylaminoimino, Bis-[(Ci-C7)- Alkyljaminoimino, Aryl-(Ci-C7)-alkylaminoimino, Aryl[(Ci-C7)- alkyljaminoimino, (C3-C7)-Cycloalkyl[(Ci-C7)-alkyl]aminoimino, (C3-C7)- CycSoalkyl-(Ci-C7)-alkylaminoimino, Heterocyclylaminoimino, Heteroaryl- (Ci-C7)-alkoxy-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkoxy-(Ci-C7)-alkyl, Heteroarylaminoimino, (C 3 -C 7) -cycloalkylaminoimino, bis - [(C 1 -C 7) -alkylaminoimino, aryl- (C 1 -C 7) -alkylaminoimino, aryl [(C 1 -C 7) -alkylaminoimino, (C 3 -C 7) -cycloalkyl [( C 1 -C 7) -alkyl] aminoimino, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkylaminoimino, heterocyclylaminoimino, heteroaryl- (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryl- (Ci -C 7) -alkoxy- (C 1 -C 7 ) -alkyl,
HeterocycSyl-N-(Ci-C7)-aSkyl, Aryl-[(Ci-C7)-alkyi]amino-(Ci-C7)-alkyl, Aryl- (Ci-C7)-alkyl[(Ci-C/)-alkyl]amino-(Ci-C7)-alkyl, (Ci-C7)-A!koxycarbonyl- (Ci-C7)-alkylamino-(Ci-C7)-alkyl, (Ci-C7)-A!koxycarbonyl-(Ci-C7)- alkyl[(Ci-C7)-alky!]amino-(Ci-C/)-alkyl, Heteroaryl-[(Ci-C7)-alkyl]amino- (Ci-C/)-alkyl, Heteroaryl-(Ci-C/)-alkyl-[(Ci-C/)-alkyl]amino-(Ci-C7)-alkyl, (C3-C7)-Cycloalky!-[(Ci-C7)-alkyl]amino-(Ci-C/)-alkyl, (C3-C7)- Cycloalkylamino-(Ci-C/)-alkyl, Aryl-(Ci-C7)-alkoxy-(Ci-C/)-alkylaryl, Heterocyclyl-N-(Ci-C/)-alkylaryl, Aryl[(Ci-C/)-alkyl]amino-(Ci-C/)- alkylaryl, Aryl-(Ci-C/)-alkyl[(Ci-C7)-alkyl]amino-(Ci-C7)-alkylaryl, (C1-C7)- Alkoxycarbonyl-(Ci-C )-alkylamino-(Ci-C/)-alkylaryl, (C1-C7)- Alkoxycarbonyl-(Ci-C7)-alkyl[(Ci-C/)-alkyl]amino-(Ci-C/)-alkylaryl, Heteroaryl[(Ci-C7)-alky!]amino-(Ci-C7)-alkyiaryl, Heteroary!-(Ci-C7)- a!kyl[(Ci-C/)-alkyl]amino-(Ci-C/)-alkylaryl, (C3-C/)-Cycloalkyl[(Ci-C )- alkyl]amino-(Ci-C/)-alkylaryl, (C3-C )-Cycloalkylamino-(Ci-C )-alkylaryl, (Ci-C/)-Alkoxy[(Ci-C/)-alkoxy]-(Ci-C/)-alkylaryl steht, zusätzlich, wenn X für ein Sauerstoffatom oder X für ein Schwefelatom steht, für (Ci-C )-Haloalkyl, (Ci-C/)-Alkoxy-(Ci-C/)-haloalkyl, (C3-C7)- Halocycloalkyl, (Ci-C/)-Haloalkoxy-(Ci-C/)-haloalkyl, Aryl-(Ci-C/)- haloalkyl, (Ci-C/)-Alkylthio-(Ci-C/)-haloalkyl, Bis[(Ci-C/)-alkyl]amino-Heterocycyl-N- (C 1 -C 7 ) -alkyl, aryl- [(C 1 -C 7 ) -alkyl] amino- (C 1 -C 7 ) -alkyl, aryl- (C 1 -C 7 ) -alkyl [(C 1 -C 4 -cyclo) ) -alkyl] amino- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkylamino- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkyl! koxycarbonyl- (Ci-C 7 ) - alkyl [(Ci-C 7 ) -alky!] amino- (Ci-C /) -alkyl, heteroaryl - [(Ci-C 7 ) -alkyl] amino- (Ci-C /) - alkyl, heteroaryl- (Ci -C () alkyl [(C 1 -C 4) alkyl] amino (C 1 -C 7) alkyl, (C 3 -C 7) cycloalkyl] - [(C 1 -C 7) alkyl] amino (C 1 -C 7) alkyl; -C () -alkyl, (C3-C7) -cycloalkylamino- (Ci-C /) -alkyl, aryl- (Ci-C7) -alkoxy- (Ci-C /) -alkylaryl, heterocyclyl-N- (ci) C 1 -) alkylaryl, aryl [(C 1 -C 4) -alkyl] amino- (C 1 -C 4) -alkylaryl, aryl- (C 1 -C 4) -alkyl [(C 1 -C 7) -alkyl] amino- C 1 -C 7) -alkylaryl, (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 4) -alkylamino- (C 1 -C 8) -alkylaryl, (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 7) -alkyl [(Ci -C () alkyl] amino (Ci-C /) - alkylaryl, heteroaryl [(Ci-C7) -alky!] Amino- (Ci-C7) -alkyiaryl, heteroaryl - (Ci-C 7 ) - a ! kyl [(Ci-C /) -alkyl] amino- (Ci-C /) -alkylaryl, (C 3 -C /) -cycloalkyl [(Ci-C) -alkyl] amino- (Ci-C /) - alkylaryl, (C3-C) -cycloalkylamino- (Ci-C) -alkylaryl, (Ci-C /) -alkoxy [(Ci-C /) -alkoxy] - (Ci-C /) -alkylaryl, in addition, if X is an oxygen atom or X is a sulfur atom, for (Ci-C) -haloalkyl, (Ci-C /) - alkoxy (Ci-C /) - haloalkyl, (C3-C7) - Halocycloa alkyl, (Ci-C /) - haloalkoxy- (Ci-C /) - haloalkyl, aryl- (Ci-C /) - haloalkyl, (Ci-C /) - alkylthio (Ci-C /) - haloalkyl, bis [(Ci-C /) - alkyl] amino-
(Ci-C7)-alkoxy-(Ci-C7)-haloalkyl steht, für Wasserstoff, Hydroxy, (d-C/)-Alkyl, (C3-C7)-Cycloalkyl, (C3-C7)- Halocycloalkyl, Brom, Chlor, (C2-C/)-Alkenyl-(Ci-C )-alkyl, (C1-C7)- Haloalkyl, (C2-C )-Alkinyl, (C2-C )-Alkenyl, Cyano-(Ci-C/)-alkyl, Nitro- (Ci-Cz)-alkyl, Amino-(Ci-C/)-alkyl, Alkyl-(Ci-C/)-amino-(Ci-C/)-alkyl, Bis- [(Ci-C/)-Alkyl]amino-(Ci-C )-alkyl, (C2-C/)-Alkinyl-(Ci-C )-alkyl, Aryl- (d-C/)-alkyl, Heteroaryl-(Ci-C/)-alkyl, Heterocyclyl-(Ci-C/)-alkyl, (C1-C7)- Alkylcarbonyl, (Ci-C/)-Alkoxycarbonyl, (C3-C/)-Cycloalkoxycarbonyl, (Ci-C/J-Alkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (C3-C7)- Cycloalkylsulfonyl, (Ci-C/)-Alkylsulfinyl, Arylsulfinyl, (C3-C7)- Cycloalkylsulfinyl, (Ci-C7)-Alkoxycarbonyl-(Ci-C/)-alkyl, Aryl, Heteroaryl, Heterocyclyl, Aminocarbonyl-(Ci-C/)-alkyl, (d-C )-Alkylaminocarbonyl- (Ci-C/)-alkyl, Bis-[(Ci-C7)-alkyl]aminocarbonyl-(Ci-C7)-alkyl, (C3-C7)- Cycloalkylaminocarbonyl-(Ci-C/)-alkyl, Hydroxycarbonyl-(Ci-C/)-alkyl, Amino, (Ci-C )-Alkylamino, Arylamino, (Ci-Cz)-Alkoxy steht und (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -haloalkyl, for hydrogen, hydroxy, (dC /) - alkyl, (C 3 -C 7 ) -cycloalkyl, (C3-C7) - halocycloalkyl, bromine , Chloro, (C 2 -C 10) -alkenyl- (C 1 -C 4) -alkyl, (C 1 -C 7) -haloalkyl, (C 2 -C) -alkynyl, (C 2 -C 6) -alkenyl, cyano- (Ci -C () alkyl, nitro (Ci-Cz) alkyl, amino (Ci-C /) - alkyl, alkyl (Ci-C /) - amino- (Ci-C /) - alkyl, Bis- [(C 1 -C 4) -alkyl] amino- (C 1 -C 4) -alkyl, (C 2 -C 6) -alkynyl- (C 1 -C 4) -alkyl, aryl- (C 1 -C 4) -alkyl, heteroaryl- Ci-C /) - alkyl, heterocyclyl (Ci-C /) - alkyl, (C1-C7) - alkylcarbonyl, (Ci-C /) - alkoxycarbonyl, (C3-C /) - cycloalkoxycarbonyl, (Ci-C / J-alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C3-C7) -cycloalkylsulfonyl, (Ci-C /) -alkylsulfinyl, arylsulfinyl, (C3-C7) -cycloalkylsulfinyl, (Ci-C7) -alkoxycarbonyl- (Ci-C /) - alkyl, aryl, heteroaryl, heterocyclyl, aminocarbonyl- (Ci-C /) - alkyl, (dC) -alkylaminocarbonyl- (Ci-C /) -alkyl, bis - [(Ci-C 7 ) -alkyl] aminocarbonyl- (Ci -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkylaminocarbonyl- (C 1 -C 4 ) -alkyl, hydroxycarbonyl- (C 1 -C 4 ) -alkyl, amino, (C 1 -C 4) -alkyl lamino, arylamino, (C 1 -C 6) -alkoxy and
Z2 für Wasserstoff, (Ci-C7)-Alkyl, (C3-C7)-Cyc!oalkyl, (Ci-C7)-Haloalkyl, Z 2 is hydrogen, (Ci-C7) alkyl, (C 3 -C 7) -Cyc! Oalkyl, (Ci-C7) haloalkyl,
(C2-C7)-Alkinyl, (C2-C/)-Alkenyl, Cyano-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkyl, Heteroaryl-(Ci-C/)-alkyl, (Ci-C/)-Alkylcarbonyl, (Ci-C7)-AlkoxycarbonyS steht oder (C 2 -C 7) -alkynyl, (C 2 -C /) - alkenyl, cyano (Ci-C7) alkyl, aryl (Ci-C7) alkyl, heteroaryl (Ci-C /) -alkyl, (Ci-C /) - alkylcarbonyl, (Ci-C 7 ) -AlkoxycarbonyS stands or
Z1 und Z2 zusammen mit dem Atomen, an das sie gebunden sind, einen Z 1 and Z 2 together with the atom to which they are attached, one
vollständig gesättigten oder teilgesättigten, gegebenenfalls durch  fully saturated or partially saturated, if necessary
Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden oder  Heteroatome form interrupted and optionally further substituted 5 to 7-membered ring or
Z1 und Z2 zusammen eine N-(Bis-(Ci-C )-alkyl)sulfanyliden-, N-(Aryl-(Ci-C7)- alkyl)sulfanyliden-, N-(Bis-(C3-C )-Cycloalkyl)sulfanyliden-, N-((Ci-C7)-Z 1 and Z 2 together form a N- (bis (Ci-C) alkyl) sulfanylidene, N- (aryl (Ci-C 7 ) - alkyl) sulfanyliden-, N- (bis (C 3 -C ) -Cycloalkyl) sulfanylidene, N - ((Ci-C 7 ) -
Alkyl-(C3-C7)-cycloalkyl)sulfanylidengruppe oder eine N,N-di-(Ci-C/)- alkylformylidengruppe bilden. Alkyl (C 3 -C 7 ) cycloalkyl) sulfanylidene group or an N, N-di- (C 1 -C 8) -alkylformylidene group.
Behandlung von Pflanzen, umfassend die Applikation einer zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren wirksamen, nicht-toxischen Menge einer oder mehrerer der Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3. Treatment of plants comprising the application of a non-toxic amount of one or more of the compounds of the formula (I) which is effective for increasing the resistance of plants to abiotic stress factors, or in each case their salts according to one of Claims 1 to 3.
Behandlung gemäß Anspruch 4, wobei die abiotischen Stressbedingungen einer oder mehrerer Bedingungen ausgewählt aus der Gruppe bestehend aus Dürre, Kältestress, Hitzestress, Trockenstress, osmotischem Stress, Staunässe, erhöhtem Bodensalzgehalt, erhöhtem Ausgesetztsein an Mineralien, The treatment of claim 4, wherein the abiotic stress conditions include one or more conditions selected from the group consisting of drought, cold stress, heat stress, drought stress, osmotic stress, waterlogging, increased soil salt content, increased exposure to minerals,
Ozonbedingungen, Starklichtbedingungen, beschränkter Verfügbarkeit von Stickstoffnährstoffen und beschränkter Verfügbarkeit von Phosphornährstoffen entsprechen. Ozone conditions, high light conditions, limited availability of nitrogen nutrients and limited availability of phosphorus nutrients.
6. Verwendung einer oder mehrerer Verbindungen der Forme! (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3 in der Sprühapplikation auf Pflanzen und Pflanzenteilen in Kombinationen mit einem oder mehrer 6. Use of one or more compounds of the forms! (I), or in each case their salts according to any one of claims 1 to 3 in the spray application to plants and plant parts in combinations with one or more
Wirkstoffen ausgewählt aud der Gruppe der Insektizide, Lockstoffe, Akarizide, Fungizide, Nematizide, Herbizide, wachstumsreguiatorische Stoffe, Safener, die Pflanzenreife beeinflussende Stoffe und Bakterizide.  Active substances selected from the group of insecticides, attractants, acaricides, fungicides, nematicides, herbicides, growth-regulating substances, safeners, substances affecting plant maturity and bactericides.
7. Verwendung einer oder mehrerer Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3 in der Sprühapplikation auf Pflanzen und Pflanzenteilen in Kombinationen mit Düngemitteln. 7. Use of one or more compounds of the formula (I), or in each case their salts according to one of claims 1 to 3 in the spray application to plants and plant parts in combinations with fertilizers.
8. Verwendung einer oder mehrerer Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3 zur Applikation auf 8. Use of one or more compounds of the formula (I), or in each case their salts according to one of claims 1 to 3 for application
gentechnisch veränderten Sorten, deren Saatgut, oder auf Anbauflächen auf denen diese Sorten wachsen.  genetically modified varieties, their seed, or on arable land on which these varieties grow.
9. Verwendung von Sprühlösungen, die eine oder mehrere der Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3 enthalten, zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren. 9. Use of spray solutions containing one or more of the compounds of the formula (I), or in each case their salts according to one of claims 1 to 3, for increasing the resistance of plants to abiotic stress factors.
10. Verfahren zur Erhöhung der Stresstoleranz bei Pflanzen ausgewählt aus der Gruppe der Nutzpflanzen, Zierpflanzen, Rasenarten, oder Bäumen, dadurch gekennzeichnet, dass die Applikation einer ausreichenden, nicht-toxischen Menge einer oder mehrere Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3 auf die Fläche, wo die 10. A method for increasing the stress tolerance in plants selected from the group of crops, ornamental plants, lawn species, or trees, characterized in that the application of a sufficient, non-toxic amount of one or more compounds of formula (I), or in each case their salts according to one of claims 1 to 3 on the area where the
entsprechende Wirkung gewünscht wird, umfassend die Anwendung auf die Pflanzen, deren Saatgut oder auf die Fläche auf der die Pflanzen wachsen, erfolgt.  corresponding effect is desired, comprising the application to the plants whose seeds or on the surface on which the plants grow takes place.
1 1 . Verfahren gemäß Anspruch 10, wobei die Widerstandsfähigkeit der so 1 1. A method according to claim 10, wherein the resistance of the
behandelten Pflanzen gegenüber abiotischem Stress gegenüber nicht behandelten Pflanzen unter ansonsten gleichen physiologischen Bedingungen um mindestens 3% erhöht ist. not treated against abiotic stress treated plants is increased by at least 3% under otherwise identical physiological conditions.
Haloalkyl-substituierte 2-Amidobenzoxazole und 2-Amidobenzothiazole der allgemeinen Formel (I) oder deren Salze, Haloalkyl-substituted 2-amidobenzoxazoles and 2-amidobenzothiazoles of the general formula (I) or salts thereof,
worin wherein
R\ R2, R3 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C8)-Alkyl,R 1 , R 3 independently of one another represent hydrogen, halogen, (C 1 -C 8 ) -alkyl,
(C3-C8)-Cycloalkyl, (C4-C8)-Cycloalkenyl, (C3-C8)-Halocycloalkyl, (C2-C8)- Alkenyl, (C2-C8)-Alkinyl, gegebenenfalls substituiertes Phenyl, Aryl- (Ci-C8)-alkyl, Aryl-(C2-C8)-alkenyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio, (Ci-Cs)-Haloalkylthio, (Ci-C8)-Haloalkyl, (Ci-Cs)-Alkoxy, (Ci-Cs)-Haloalkoxy, (C3-C8)-Cycloalkoxy, (C3-C8)-Cycloalkyl-(Ci-C8)- alkoxy, Aryloxy, Heteroraryloxy, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy, (C2-C8)- Alkinyl-(Ci-C8)-alkoxy, (C2-C8)-Alkenyloxy, Bis-[(Ci-C8)-alkyl]amino- (Ci-Cs)-alkoxy, Tris-[(Ci-C8)-alkyl]silyl, Bis-[(Ci-C8)-alkyl]arylsilyl, Bis- [(Ci-C8)-alkyl]-(Ci-C8)-alkylsilyl, Tris-[(Ci-C8)-alkyl]silyl-(C2-C8)-alkinyl, Aryl-(C2-C8)-alkinyl, Heteroaryl-(C2-C8)-alkinyl, (Ci-C8)-Alkyl-(C2-C8)- alkinyl, (C3-C8)-Cycloalkyl-(C2-C8)-alkinyl, (Ci-C8)-Haloalkyl-(C2-C8)- alkinyl, Heterocyclyl-N-(Ci-C8)-alkoxy, Nitro, Cyano, Amino, (Ci-C8)- Alkylamino, Bis-[(Ci-C8)-alkyl]amino, (Ci-C8)- Alkylcarbonylamino, (C3-C8)-Cycloalkylcarbonylamino, Arylcarbonylamino, (Ci-C8)- Alkoxycarbonylamino, Heterocyciyl-(Ci-C8)-alkoxy, (C3-C8)- Cycloalkyl- (Ci-Cs)-alkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, Heterocyclyl- (C2-C8)-alkinyl, (C3-C8)-Halocycloalkoxy, (C2-C8)-Haloalkinyloxy, Arylthio, Heteroarylthio, (Ci-C8)-Alkylsulfinyl, (Ci-C8)-Haloalkylsulfinyl, Arylsulfinyl, Heteroarylsu!finyl, (Ci-CeJ-Alkylsulfonyl, (Ci-CeJ-Haloalkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, Thiocyanato, Isothiocyanato, (C3-C-8)- Cycloalkylamino, (C3-C8)-Cycloalkyl[(Ci-C8)-alkyl]amino, (C2-C8)- Alkenylamino stehen, (C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C 3 -C 8 ) -halocycloalkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, optionally substituted phenyl, aryl- (Ci-C 8) alkyl, aryl (C 2 -C 8) alkenyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, heterocyclyl, heterocyclyl (Ci-C 8) -alkyl , (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio, (C 1 -C 8 ) -haloalkylthio, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) alkoxy, (Ci-Cs) haloalkoxy, (C 3 -C 8) cycloalkoxy, (C 3 -C 8) cycloalkyl (Ci-C8) - alkoxy, aryloxy, Heteroraryloxy, (Ci-C 8) alkoxy (Ci-C 8) alkoxy, (C 2 -C 8) - alkynyl, (Ci-C 8) alkoxy, (C 2 -C 8) alkenyloxy, - bis [(Ci-C 8) alkyl] amino- (C 1 -C 8 ) -alkoxy, tris - [(C 1 -C 8 ) -alkyl] silyl, bis - [(C 1 -C 8 ) -alkyl] arylsilyl, bis- [(C 1 -C 8 ) alkyl] - (Ci-C8) alkylsilyl, tris - silyl [(Ci-C 8) alkyl] (C 2 -C 8) alkynyl, aryl (C 2 -C 8) -alkynyl, heteroaryl, (C 2 -C 8 ) -alkynyl, (C 1 -C 8 ) -alkyl- (C 2 -C 8 ) -alkynyl, (C 3 -C 8 ) -cycloalkyl- (C 2 -C 8 ) -alkynyl, (Ci-C 8) haloalkyl (C 2 -C 8) - alkynyl, hetero cyclyl-N- (Ci-C8) alkoxy, nitro, cyano, amino, (Ci-C8) - alkylamino, - bis [(Ci-C 8) alkyl] amino, (Ci-C 8) - alkylcarbonylamino , (C 3 -C 8) -Cycloalkylcarbonylamino, arylcarbonylamino, (Ci-C 8) - alkoxycarbonylamino, Heterocyciyl- (Ci-C 8) alkoxy, (C 3 -C 8) - cycloalkyl (Ci-Cs) alkyl , (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, heterocyclyl (C 2 -C 8 ) -alkynyl, (C 3 -C 8 ) -halocycloalkoxy, (C 2 -C 8 ) Haloalkynyloxy, arylthio, heteroarylthio, (C 1 -C 8 ) -alkylsulfinyl, (C 1 -C 8 ) -haloalkylsulfinyl, arylsulfinyl, Heteroarylsuccinyl, (C 1 -C 6 -alkylsulfonyl, (C 1 -C 12 -alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, thiocyanato, isothiocyanato, (C 3 -C 8 ) -cycloalkylamino, (C 3 -C 8 ) -cycloalkyl [(C 1 -C 8 ) -alkyl] amino, (C 2 -C 8 ) -alkenylamino,
R1 und R2 mit den Atomen, an die sie gebunden sind, einen vollständig R 1 and R 2 with the atoms to which they are attached, a complete
gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden,  form saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring,
R2 und R3 mit den Atomen, an die sie gebunden sind, einen vollständig R 2 and R 3 with the atoms to which they are attached, a complete
gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden,  form saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring,
W für Sauerstoff, Schwefel steht, W stands for oxygen, sulfur,
X für Sauerstoff, Schwefel steht, X stands for oxygen, sulfur,
Q für (Ci-C8)-Haloalkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, (C3-C8)- Halocycloalkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-haloalkyl, Aryl-(Ci-C8)- haloalkyl, (Ci-C8)-Alkylthio-(Ci-C8)-haloalkyl, Bis[(Ci-C8)-alkyl]amino-Q (8 Ci-C) alkoxy (Ci-C8) -haloalkyl, (C 3 -C 8) (Ci-C 8) haloalkyl, - halocycloalkyl, (Ci-C8) haloalkoxy (C -C 8) haloalkyl, aryl (Ci-C8) - haloalkyl, (Ci-C8) alkylthio (Ci-C8) -haloalkyl, amino-bis [(Ci-C 8) alkyl]
(Ci-C8)-alkoxy-(Ci-C8)-haloalkyl steht, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl,
Z1 für Wasserstoff, Hydroxy, (Ci-C8)-Alkyl, (C3-C8)-Cycloalkyl, (C3-C8)-Z 1 represents hydrogen, hydroxy, (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) -
Halocycloalkyl, Halogen, (C2-C8)-Alkenyl-(Ci-C8)-alkyl, (Ci-C8)-Haloalkyl, (C2-C8)-Alkinyl, (C2-C8)-Alkenyl, Cyano-(Ci-C8)-alkyl, Nitro-(Ci-C8)-alkyl, Amino-(Ci-C8)-alkyl, Alkyl-(Ci-C8)-amino-(Ci-C8)-alkyl, Bis-[(Ci-Ce)- Alkyl]amino-(Ci-C8)-alkyl, (C2-C8)-Alkinyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-CeJ-Alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (Ci-Ce)- Alkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, (Ci-C8)-Alkylsulfinyl, Arylsulfinyl, (C3-C8)-Cycloalkylsulfinyl, (Ci-Ce)- Alkoxycarbonyl-(Ci-C8)-alkyl, Aryl, Heteroaryl, Heterocyclyl, Aminocarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylaminocarbonyl-(Ci-C8)-alkyl, Bis-[(Ci-C8)-a!kyl]aminocarbonyl-(Ci-C8)-alkyl, (C3-C8)- Cycloalkylaminocarbonyl-(Ci-C8)-alkyl, Hydroxycarbonyl-(Ci-C8)-alkyl, Amino, (Ci-C8)-Alkylamino, Arylamino, (Ci-Cs)-Alkoxy steht Halocycloalkyl, halogen, (C 2 -C 8) alkenyl (Ci-C 8) alkyl, (Ci-C8) -haloalkyl, (C 2 -C 8) -alkynyl, (C 2 -C 8) alkenyl , cyano (Ci-C 8) alkyl, nitro, (Ci-C 8) alkyl, amino (Ci-C 8) alkyl, alkyl (Ci-C 8) amino (Ci-C 8 ) alkyl, - bis [(Ci-Ce) - alkyl] amino- (Ci-C 8) alkyl, (C 2 -C 8) alkynyl (Ci-C 8) alkyl, aryl (Ci- C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, (C 1 -C 6 -alkoxycarbonyl, (C 3 -C 8 ) - cycloalkoxycarbonyl, (Ci-Ce) - alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C3-C8) cycloalkylsulfonyl, (Ci-C8) alkylsulfinyl, arylsulfinyl, (C 3 -C 8) cycloalkylsulfinyl, (Ci-Ce) - alkoxycarbonyl - (C 1 -C 8) -alkyl, aryl, heteroaryl, heterocyclyl, Aminocarbonyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylaminocarbonyl- (C 1 -C 8 ) -alkyl, bis - [(C 1 -C 8 ) -alkyl] aminocarbonyl- (C 1 -C 8 ) -alkyl, (C 3 -C 8) - cycloalkylaminocarbonyl (Ci-C 8) alkyl, hydroxycarbonyl- (Ci-C 8) alkyl, amino, (Ci-C 8) alkylamino, arylamino, (Ci-Cs) alkoxy stands
Z2 für Wasserstoff, (Ci-Cs)-Alkyl, (C3-C8)-Cycloalkyl, (Ci-C8)-Haloalkyl,Z 2 is hydrogen, (C 1 -C 5 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 1 -C 8 ) -haloalkyl,
(C2-C8)-Alkinyl, (C2-C8)-AlkenyS, Cyano-(Ci-C8)-alkyS, Aryl-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-Cs)-Alkoxycarbonyl steht oder (C 2 -C 8 ) -alkynyl, (C 2 -C 8 ) -alkenyl, cyano- (C 1 -C 8 ) -alkyS, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, (C 1 -C 8 ) -alkoxycarbonyl or
Z1 und Z2 zusammen mit dem Atomen, an das sie gebunden sind, einen Z 1 and Z 2 together with the atom to which they are attached, one
vollständig gesättigten oder teilgesättigten, gegebenenfalls durch  fully saturated or partially saturated, if necessary
Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden oder  Heteroatome form interrupted and optionally further substituted 5 to 7-membered ring or
Z1 und Z2 zusammen eine N-(Bis-(Ci-C6)-alkyl)sulfanyliden-, N-(Aryl-(Ci-Ce)- alkyl)sulfanyliden-, N-(Bis-(C3-C/)-Cycloalkyl)sulfanyliden-, N-((Ci-C6)- Alkyl-(C3-C/)-cycloalkyl)sulfanylidengruppe oder eine N,N-di-(Ci-Ce)- alkylformylidengruppe bilden. Z 1 and Z 2 together form an N- (bis (C 1 -C 6) -alkyl) sulfanylidene, N- (aryl- (C 1 -C 6) -alkyl) sulfanylidene, N- (bis- (C 3 -C / ) -Cycloalkyl) sulfanylidene, N - ((Ci-C 6 ) - alkyl (C 3 -C /) - cycloalkyl) sulfanylidengruppe or an N, N-di- (Ci-Ce) - form alkylformylidengruppe.
13. Haloalkyl-substituierte 2-Amidobenzoxazole und 2-Amidobenzothiazole gemäß Anspruch 12, worin 13. Haloalkyl-substituted 2-amidobenzoxazoles and 2-amidobenzothiazoles according to claim 12, wherein
R1, R2, R3 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C-4)-Alkyl,R 1 , R 2 , R 3 independently of one another represent hydrogen, halogen, (C 1 -C 4) -alkyl,
(C3-C8)-Cycloalkyl, (C4-C8)-Cycloalkenyl, (C3-C8)-Halocycloalkyl, (C2-C4)- Alkenyl, (C2-C4)-Alkinyl, gegebenenfalls substituiertes Phenyl, Aryl- (Ci-C4)-alkyl, Aryl-(C2-C4)-alkenyl, Heteroaryl, Heteroaryl-(Ci-C4)-alkyl, HeterocyclyS, Heterocyclyl-(Ci-C4)-alkyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio, (Ci-C4)-Haloalkylthio, (Ci-C4)-Haloalkyl, (Ci-C4)-Alkoxy, (Ci-C4)-Ha!oalkoxy, (C3-C8)-Cycloalkoxy, (C3-C8)-Cycloalkyl-(Ci-C4)- alkoxy, Aryloxy, Heteroraryloxy, (Ci-C4)-Alkoxy-(Ci-C4)-aikoxy, (C2-C4)-(C 3 -C 8) cycloalkyl, (C 4 -C 8) cycloalkenyl, (C 3 -C 8) halocycloalkyl, (C2-C4) - alkenyl, (C2-C4) -alkynyl, optionally substituted phenyl, aryl (C 1 -C 4) -alkyl, aryl- (C 2 -C 4) -alkenyl, heteroaryl, heteroaryl- (C 1 -C 4) -alkyl, heterocyclyS, heterocyclyl- (C 1 -C 4) -alkyl, (C 1 -C 4) -alkoxy - (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -haloalkylthio, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (Ci-C 4 ) -Ha! Oalkoxy, (C 3 -C 8 ) -cycloalkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 4 ) -alkoxy, aryloxy, heteroaryloxy, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -cycloalkoxy, C4) -aikoxy, (C2-C4) -
Alkinyl-(Ci-C4)-alkoxy, (C2-C4)-Alkenyloxy, Bis-[(Ci-C4)-alkyl]amino- (Ci-C4)-alkoxy, Tris-[(Ci-C4)-alkyl]silyl, Bis-[(Ci-C4)-alkyl]arylsilyl, Bis- [(Ci-C4)-alkyl]-(Ci-C4)-alkylsilyl, Tris-[(Ci-C4)-alkyl]silyl-(C2-C4)-alkinyl, Aryl-(C2-C4)-alkinyl, Heteroaryl-(C2-C4)-alkinyl, (Ci-C4)-Alkyl-(C2-C4)- alkinyl, (C3-C8)-Cycloalky!-(C2-C4)-alkinyl, (Ci-C4)-Haloaikyl-(C2-C4)- alkinyl, Heterocyclyl-N-(Ci-C4)-alkoxy, Nitro, Cyano, Amino, (C1-C4)- Alkylamino, Bis-[(Ci-C4)-alkyl]amino, (C1-C4)- Alkylcarbonylamino, (C3-C8)-Cycloalkylcarbonylamino, Arylcarbonylamino, (C1-C4)- Alkoxycarbonylamino, Heterocyclyl-(Ci-C4)-alkoxy, (Cß-Ce)- Cycloalkyl- (Ci-C4)-alkyl, (C2-C4)-Haloalkenyl, (C2-C4)-Haloalkinyl, Heterocyclyl-Alkynyl (Ci-C 4) alkoxy, (C 2 -C 4) alkenyloxy, - bis [(Ci-C 4) alkyl] amino- (Ci-C 4) alkoxy, tris - [(Ci- C 4 ) -alkyl] silyl, bis - [(C 1 -C 4 ) -alkyl] arylsilyl, bis- [(C 1 -C 4 ) -alkyl] - (C 1 -C 4 ) -alkylsilyl, tris - [(C 1 -C 4 ) alkyl] silyl (C2-C4) alkynyl, aryl (C 2 -C 4) alkynyl, heteroaryl (C2-C4) -alkynyl, (Ci-C4) alkyl- (C2-C 4 ) alkynyl, (C 3 -C 8 ) cycloalky! (C 2 -C 4 ) alkynyl, (C 1 -C 4 ) -haloalkyl (C 2 -C 4 ) -alkynyl, heterocyclyl-N- (C 1 -C 4 ) -alkoxy , Nitro, cyano, amino, (C 1 -C 4) -alkylamino, bis - [(C 1 -C 4) -alkyl] -amino, (C 1 -C 4) -alkylcarbonylamino, (C 3 -C 8) -cycloalkylcarbonylamino, arylcarbonylamino, (C 1 -C 4 ) - alkoxycarbonylamino, heterocyclyl- (C 1 -C 4 ) -alkoxy, (C 3 -C 4 ) -cycloalkyl- (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -haloalkenyl, (C 2 -C 4 ) -haloalkynyl, heterocyclyl -
(C2-C4)-alkinyl, (C3-C8)-Halocycloalkoxy, (C2-C4)-Ha!oalkinyloxy, Arylthio, Heteroarylthio, (Ci-C4)-Alkylsuifinyl, (Ci-C4)-Haloaikylsulfinyi, Arylsulfinyl, Heteroaryisuifinyl, (Ci-C4)-Aikylsuifonyl, (Ci-C4)-Haloalkylsulfonyi, Aryisulfonyl, Heteroarylsuifonyl, Thiocyanato, Isothiocyanato, (C3-C8)- Cycloalkylamino, (C3-C8)-Cycloaikyi[(Ci-C4)-alky!]amino, (C2-C4)-(C 2 -C 4) -alkynyl, (C 3 -C 8) -halocycloalkoxy, (C 2 -C 4) -haloalkynyloxy, arylthio, heteroarylthio, (C 1 -C 4) -alkylsulfinyl, (C 1 -C 4) -haloalkylsulfinyl, arylsulfinyl, heteroaryisuifinyl, (C 1 -C 4 ) -alkylsulfonyl, (C 1 -C 4 ) -haloalkylsulfonyi, arylsulfonyl, heteroarylsuifonyl, thiocyanato, isothiocyanato, (C 3 -C 8 ) -cycloalkylamino, (C 3 -C 8 ) -cycloalkyl [(C 1 -C 4) -alky! ] amino, (C2-C4) -
Alkenyiamino stehen, Alkenyiamino stand,
R1 und R2 mit den Atomen, an die sie gebunden sind, einen vollständig R 1 and R 2 with the atoms to which they are attached, a complete
gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden,  form saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring,
R2 und R3 mit den Atomen, an die sie gebunden sind, einen vollständig R 2 and R 3 with the atoms to which they are attached, a complete
gesättigten, teilgesättigten oder ungesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden,  form saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring,
W für Sauerstoff, Schwefel steht, X für Sauerstoff, Schwefe! steht, W stands for oxygen, sulfur, X for oxygen, sulfur! stands,
Q für (Ci-C7)-Haloalky!, (Ci-C4)-Alkoxy-(Ci-C4)-haloa!kyl, (C3-C8)-Q is (Ci-C 7) -Haloalky !, (Ci-C 4) alkoxy (Ci-C 4) -haloa alkyl, (C 3 -C 8)! -
Halocycloalkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-haloa!kyl, Aryl-(Ci-C4)- haloalkyl, (Ci-C4)-Alkylthio-(Ci-C4)-haloa!ky!, Bis[(Ci-C4)-alkyl]amino- (Ci-C4)-alkoxy-(Ci-C4)-haloalkyl steht, ! Halocycloalkyl, (Ci-C4) haloalkoxy (C 4) -haloa alkyl, aryl (Ci-C4) - haloalkyl, (C 4) alkylthio (C 4) -haloa ! ky !, bis [(C 1 -C 4 ) -alkyl] amino- (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -haloalkyl,
Z1 für Wasserstoff, Hydroxy, (Ci-C4)-Alkyl, (C3-C8)-Cycloalkyl, (C3-C8)-Z 1 is hydrogen, hydroxy, (C 1 -C 4 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -
Halocycloalkyl, Halogen, (C2-C4)-Alkenyl-(Ci-C4)-alkyl, (Ci-C4)-Haloalkyl, (C2-C4)-Alkinyl, (C2-C4)-Alkenyl, Cyano-(Ci-C4)-alkyl, Nitro-(d-C4)-alkyl, Amino-(Ci-C4)-alkyl, Alkyl-(Ci-C )-amino-(Ci-C4)-alkyl, Bis-[(Ci-C4)- Alkyl]amino-(Ci-C4)-alkyl, (C2-C4)-Alkinyl-(Ci-C4)-alkyl, Aryl-(Ci-C4)-alkyl, Heteroaryl-(Ci-C4)-alkyl, Heterocyclyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylcarbonyl, (Ci-C4)-Alkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (C1-C4)- Alkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, (Ci-C4)-Alkylsulfinyl, Arylsulfinyl, (C3-C8)-Cycloalkylsulfinyl, (C1-C4)- Alkoxycarbonyl-(Ci-C4)-alkyl, Aryl, Heteroaryl, Heterocyclyl, Halocycloalkyl, halogen, (C 2 -C 4) alkenyl (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 2 -C 4) -alkynyl, (C 2 -C 4) - Alkenyl, cyano- (C 1 -C 4 ) -alkyl, nitro (C 1 -C 4 ) -alkyl, amino- (C 1 -C 4 ) -alkyl, alkyl- (C 1 -C 4 ) -amino- (C 1 -C 4 ) - alkyl, - bis [(Ci-C 4) - alkyl] amino- (Ci-C 4) alkyl, (C 2 -C 4) alkynyl (Ci-C 4) alkyl, aryl (Ci-C 4 ) -alkyl, heteroaryl- (C 1 -C 4 ) -alkyl, heterocyclyl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 4 ) -alkoxycarbonyl, (C 3 -C 8) -Cycloalkoxycarbonyl, (C 1 -C 4 ) -alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C 3 -C 6 ) -cycloalkylsulfonyl, (C 1 -C 4 ) -alkylsulfinyl, arylsulfinyl, (C 3 -C 8 ) -cycloalkylsulfinyl, (C 1 -C 4 ) - Alkoxycarbonyl- (C 1 -C 4 ) -alkyl, aryl, heteroaryl, heterocyclyl,
Aminocarbonyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylaminocarbonyl-(Ci-C4)-alkyl, Bis-[(Ci-C4)-alkyl]aminocarbonyl-(Ci-C4)-alkyl, (C3-C8)- Cycloalkylaminocarbonyl-(Ci-C4)-alkyl, Hydroxycarbonyl-(Ci-C )-alkyl, Amino, (Ci-C )-Alkylamino, Arylamino, (Ci-C4)-Alkoxy steht Aminocarbonyl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylaminocarbonyl- (C 1 -C 4 ) -alkyl, bis - [(C 1 -C 4 ) -alkyl] aminocarbonyl- (C 1 -C 4 ) - alkyl, (C 3 -C 8 ) -cycloalkylaminocarbonyl- (C 1 -C 4 ) -alkyl, hydroxycarbonyl- (C 1 -C 4 ) -alkyl, amino, (C 1 -C 4 ) -alkylamino, arylamino, (C 1 -C 4 ) - Alkoxy stands
Z2 für Wasserstoff, (Ci-C )-Alkyl, (C3-C8)-Cycloalkyl, (Ci-C4)-Haloa!kyl, Z 2 is hydrogen, (C 1 -C 4 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 1 -C 4 ) -haloalkyl,
(C2-C4)-Alkinyl, (C2-C4)-Alkenyl, Cyano-(Ci-C4)-alkyl, Aryl-(Ci-C4)-alkyl, Heteroaryl-(Ci-C4)-alkyl, (Ci-C4)-Alky!carbonyl, (Ci-C4)-Alkoxycarbonyl steht oder (C 2 -C 4) -alkynyl, (C 2 -C 4) alkenyl, cyano (Ci-C 4) alkyl, aryl (Ci-C 4) alkyl, heteroaryl (Ci-C 4) alkyl, (C 1 -C 4 ) -alkyl carbonyl, (C 1 -C 4 ) -alkoxycarbonyl or
Z1 und Z2 zusammen mit dem Atomen, an das sie gebunden sind, einen Z 1 and Z 2 together with the atom to which they are attached, one
vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unierbrochenen und gegebenenfalls weiter substituierten 5 bis 7-gliedrigen Ring bilden oder fully saturated or partially saturated, if necessary Heteroatoms unierbrochenen and optionally further substituted 5 to 7-membered ring form or
Z1 und Z2 zusammen eine N-(Bis-(Ci-C6)-alkyl)sulfanyliden-, N-(Aryl-(Ci-Ce)- alkyl)sulfanyliden-, N-(Bis-(C3-C7)-Cycloalkyl)sulfanyliden-, N-((Ci-Ce)- Alkyl-(C3-C )-cycloalkyl)sulfanylidengruppe oder eine N,N-di-(Ci-C6)- alkylformylidengruppe bilden. Z 1 and Z 2 together form a N- (bis (C 1 -C 6 ) alkyl) sulfanylidene, N- (aryl- (C 1 -C 6 ) -alkyl) sulfanylidene, N- (bis (C 3 -C 7 ) -Cycloalkyl) sulfanylidene, N - ((Ci-Ce) - alkyl (C3-C) -cycloalkyl) sulfanylidengruppe or an N, N-di- (Ci-C6) - alkylformylidengruppe.
Sprühlösung zur Behandlung von Pflanzen, enthaltend eine zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren wirksame Menge einer oder mehrerer der substituierten Isochinoline gemäß einem der Ansprüche 12 oder 13. A spray solution for the treatment of plants, comprising an amount of one or more of the substituted isoquinolines according to any of claims 12 or 13 effective to increase the resistance of plants to abiotic stresses.
EP13758839.8A 2012-09-05 2013-09-03 Use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles or salts thereof as active substances against abiotic plant stress Withdrawn EP2892345A1 (en)

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