EP2892885A1 - Herbicidally active bicycloaryl carboxylic acid amides - Google Patents

Herbicidally active bicycloaryl carboxylic acid amides

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Publication number
EP2892885A1
EP2892885A1 EP13756174.2A EP13756174A EP2892885A1 EP 2892885 A1 EP2892885 A1 EP 2892885A1 EP 13756174 A EP13756174 A EP 13756174A EP 2892885 A1 EP2892885 A1 EP 2892885A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
cycloalkyl
halo
heterocyclyl
radicals
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Withdrawn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
EP13756174.2A
Other languages
German (de)
French (fr)
Inventor
Hartmut Ahrens
Andreas Van Almsick
Ralf Braun
Arnim Köhn
Stefan Lehr
Hansjörg Dietrich
Elmar Gatzweiler
Christopher Hugh Rosinger
Dirk Schmutzler
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
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Bayer CropScience AG
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Publication date
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Priority to EP13756174.2A priority Critical patent/EP2892885A1/en
Publication of EP2892885A1 publication Critical patent/EP2892885A1/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
    • 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
    • A01N43/82—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 three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and weeds in
  • EP 1 1158258 discloses N- (tetrazol-5-yl), N- (triazol-5-yl) and N- (1, 2,5-oxadiazol-3-yl) bicycloarylcarboxamides and their use as herbicides. However, these compounds do not always show a sufficient effect against harmful plants and / or they are sometimes not sufficiently compatible with some important ones
  • Crops such as cereals, corn or rice.
  • N- (tetrazol-5-yl), N- (triazol-5-yl), N- (1, 2,5-oxadiazol-3-yl) - and N- (1, 3,4-oxadiazol-2-yl) bicycloarylcarboxylic acid amides substantially different from those known in the art
  • An object of the present invention are thus N- (tetrazol-5-yl) -, N- (triazol-5-yl) -, N- (1, 2,5-oxadiazol-3-yl) - and N- (1 , 3,4-oxadiazol-2-yl) bicycloarylcarboxamides of the formula (I) or salts thereof
  • X is nitro, halo, cyano, rhodano, (d-Ce alkyl, halo (Ci-C6) alkyl, (C 2 -C 6 ) alkenyl, halo (C 2 -C 6 ) alkenyl, (C 2 -C 6) alkynyl, halo (C 3 -C 6) -alkynyl, (C 3 - C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (C 3 -C 6) - cycloalkenyl, halo (C 3 -C 6) - cycloalkenyl, (C 3 -C 6) -cycloalkenyl, (C 3 -C 6) -cycloalkyl- (Ci-C6) alkyl, halo (C 3 -C 6) -cycloalkyl- (Ci-C6) alkyl, (C 3
  • R 2 O (O) C (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) C (R 1 ) N (O) C- (Ci-C 6 ) -alkyl,
  • R 2 (O) 2 S (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl
  • W is hydrogen, halogen, nitro, cyano, rhodano, (C 1 -C 6 -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogeno (C 2 -C 6 ) -alkenyl, (C2-C6) alkynyl, halo (C 3 - C 6) -alkynyl, (C 3 -C /) - cycloalkyl, halo (C 3 -C /) - cycloalkyl, (Ci-C 6) - Alkoxy, halogen- (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkyl- (O) n S-, (C 1 -C 6 ) -haloalkyl (O) nS-, (C 1 -C 6) - Alkoxy, hal
  • R is hydrogen, (Ci-C 6) -alkyl, Ha! Ogen (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C2-C6) alkenyl, (C 2 -C 6 ) alkynyl, halo (C 3 -C 6 ) alkynyl, (C 3 -C 6 ) cycloalkyl, halo (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) -CycSoalkyl - (Ci-C6) alkyl, halo (C 3 -C 6) - cycloalkyl- (Ci-C 6) alkyl, R 1 (O) C- (Ci-C 6) alkyl, R 1 O (O) C- (Ci-C 6) -alkyl, (R 1) 2 N (O) C- (Ci- C 6) -A!
  • R x is (C 3 -C) -cycloalkyl, heteroaryl, heterocyclyl or phenyl, where the four radicals mentioned above are in each case represented by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogen (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl,
  • R Y is hydrogen, (Ci-C 6) -A! Kyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) -a! Kenyi , (C2-C6) -Alkiny !, halo (C 3 -C 6) -alkynyl, (Cs-C / J-cycloalkyl,
  • Trifluoromethylcarbonyl halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl,
  • R z is hydrogen, (C 1 -C 6 ) -alkyl, R 1 0- (C 1 -C 6 ) -alkyl, R'CH 2 , (C 3 -C 6 ) -cycloalkyl, halogeno (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, halo (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, halo (C 3 -C 6 ) alkynyl, R 1 0 , R 1 (H) N, methoxycarbonyl, ethoxycarbonyl,
  • Heterocyclyl carries n oxo groups
  • R 1 represents hydrogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6 ) alkynyl, halo (C 3 -C 6 ) alkynyl, (Cs-CeJ-cycloalkyl, (C 3 -C 6 ) -cycloalkenyl, halo (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, cycloalkyl- (C 1 -C 6 ) -alkyl-O- (Ci C 6 ) alkyl, phenyl, phenyl (C
  • R 2 is (Ci-C 6) -alkyl, Haiogen- (Ci-C 6) alkyl, (C 2 -C 6) -Alkenyi, halo (C 2 -C 6) - alkenyl, (C 2 -C 6) -Aikinyl, halo (C3-C6) -alkynyl, (C 3 -C 6) -Cycloaikyl, (C 3 -C 6) -
  • R 3 represents hydrogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 - C 6) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
  • R 4 is (Ci-Ce) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (C 3 -C 6) - Cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
  • R 5 is hydrogen or (C 1 -C 4 ) -alkyl
  • R 6 is (C 1 -C 4 ) -alkyl
  • R 'de notes acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl,
  • L is a 3-, 4- or 5-membered fused-on, unsaturated bridge whose bridge atoms consist of t carbon atoms and m heteroatoms from the group consisting of O, S and N.
  • alkyl radicals having more than two carbon atoms may be straight-chain or branched.
  • Alkyl radicals 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.
  • alkenyl means e.g. Allyl, 1-methylprop-2-en-1-yl,
  • Alkynyl means e.g. Propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl.
  • the multiple bond can each be in any position of the unsaturated radical.
  • Cycloalkyl means a carbocyclic saturated ring system having three to six C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • cycloalkenyl is a monocyclic alkenyl group having three to six carbon ring members, e.g. Cyclopropenyl, cyclobutenyl,
  • Cyclopentenyl and cyclohexenyl, wherein the double bond may be in any position.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Heterocyclyl means a saturated, partially saturated or fully unsaturated cyclic radical containing from 3 to 6 ring atoms of which from 1 to 4 are selected from the group consisting of oxygen, nitrogen and sulfur, and which may additionally be annelated by a benzo ring.
  • heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl
  • Heteroaryl means an aromatic cyclic radical containing from 3 to 6 ring atoms of which from 1 to 4 are selected from the group consisting of oxygen, nitrogen and sulfur, and which may additionally be fused by a benzo ring.
  • heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl, 1, 2,3-oxadiazolyl, 1, 2 4-oxadiazolyl, 1, 2,5-oxadiazolyl, 1, 3,4-oxadiazolyl, 1, 2,4-triazolyl, 1, 2,3-triazolyl, 1, 2,5-triazolyl, 1, 3,4- Triazolyl, 1, 2,4-triazolyl, 1, 2,4-thiadiazolyl, 1, 3,4-thiadiazolyl, 1, 2,3-thiadiazolyl, 1, 2,5-thiadiazolyl, 2H-1,2,3, 4-tetrazolyl,
  • the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetrically substituted carbon atoms are present, enantiomers and diastereomers may occur. Likewise, stereoisomers occur when sulfoxides are present. Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants. The invention also relates to all stereoisomers and mixtures thereof which are of the general formula (I), but not specifically defined. The compounds of formula (I) can form salts. Salt formation can through
  • Suitable bases are organic amines, such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates
  • alkylsulfonium and alkylsulfoxonium salts such as (C 1 -C 4) -trialkylsulfonium and (C 1 -C 4) -trialkylsulfoxonium salts.
  • the compounds of 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. 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 a basic group, e.g. Amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • 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 salicy
  • R 7 , R 8 , R 12 , R 13 , R 22 and R 23 are each independently
  • R 1 ) 2 N (O) C, R 1 O, (R 1 ) 2 N, R 2 (O) n S, R 1 O (0) 2 S, (R 1 ) 2 N (O) 2 S and R 1 is 0- (C 1 -C 6 ) -alkyl, and wherein heterocyclyl carries n oxo groups, R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 are each independently hydrogen, halogen, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (Ci-C) alkoxy, (Ci C 4) -haloalkoxy or (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkyl or in each case two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24
  • R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 is an acetal of the formula -O- (C 2 -C 4 ) -alkylene O-,
  • R 1 1, R 18, R 19, R 26 and R 27 are each independently hydrogen, (Ci- C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl , Halo (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, halo (C 3 -C 6 ) -alkynyl, where the six radicals mentioned above are each represented by s radicals from the group consisting of nitro, cyano , R 2 (0) n S, (R 1 ) 2 N , R 1 O, R 1 (0) C, R 1 0 (0) C, R 1 (0) CO, R 2 0 (0) CO, R 1 (0) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N, (C 3 -C 6 ) -cycloalkyl, heteroaryl, heterocyclyl and phenyl, wherein the four last-menti
  • R 28, R 29, R 30 and R 31 are each independently hydrogen, nitro, halogen, cyano, thiocyanato, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6 ) alkenyl,
  • Halogeno (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, halogeno (C 3 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, halogeno (C 3 -) C6) cycloalkyl, (C3-C6) cycloalkenyl, halo (C 3 -C 6) cycloalkenyl, (C 3 - C 6) -cycloalkyl- (Ci-C (6) alkyl, halo C 3 - C6) cycloalkyl- (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkenyl, (Ci-C 6) alkyl, halo (C 3 -C 6) cycloalkenyl (C 6 ) -alkyl, R 1 (O) C, R 1 (R 1 ON ) C,
  • R 2 (O) 2 S (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl
  • Q represents a remainder Q1, Q2, Q3 or Q4,
  • X is nitro, halo, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) - alkenyl, (C 2 -C 6) -alkynyl, (C 3 -C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, halo (C 3 -C 6) cycloalkyl (C 1 -C 6 ) -alkyl, R 1 (O) C,
  • R 1 (R 1 ON ) C, R 1 O (O) C, (R 1 ) 2 N (O) C, RO, (R 1 ) 2 N, R 1 (O) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N,
  • W is hydrogen, halogen, nitro, cyano, (Ci-CeJ-alkyl, halogeno (Ci-Ce) - alkyl, (C 3 -C) -cycloalkyl, (Ci-C 6 ) -alkoxy, (Ci-C 6 ) -Alkyl- (O) n S-, R 1 O (0) C, (R 1 ) 2 N, R 1 (O) C (R 1 ) N or R 2 (O) 2 S (R 1 ) N .
  • R is hydrogen
  • R x represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 - C6) alkenyl, (C 2-C6) alkynyl, halo (C3-C6) -alkynyl, where the radicals mentioned above six respectively by s radicals selected from the group consisting (from R 2 0) n S, (R 1) 2 N, R 1 0 , R 1 (0) C, RO (0) C, R 1 (0) CO, R 2 0 (0) CO, R 1 (0) C (R 1) N, R 2 (0) 2 S (R 1 ) N, (C 3 -C 6) -cycloalkyl, heteroaryl, heterocyclyl and phenyl, where the four last-mentioned radicals are represented by s radicals from the group consisting of (C 1 -C 6 -alkyl, halogeno (C 1
  • R Y is hydrogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C /) - cycloalkyl, (Ci-C6) alkoxy, methoxycarbonyl, methoxycarbonylmethyl, halogen, amino .
  • R z is hydrogen, (C 1 -C 6 ) -alkyl, R 1 O- (C 1 -C 6 ) -alkyl, R'CH 2 , (C 3 -C 7 ) -cycloalkyl, halogeno (C 1 -C 6 ) -alkyl, R 1 O, R 1 (H) N, methoxycarbonyl, acetylamino or methylsulfonyl, R 1 represents hydrogen, (Ci-C 6) -A! KyS, halo (Ci-C 6) alkyl, (C3-C 6) -Cyc!
  • R 2 is (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) cycloalkyl, halo (C 3 - C 6) cycloalkyl, (C3-C6 ) -Cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl,
  • R 3 is hydrogen or (C 1 -C 6 ) -alkyl
  • R 4 is (C 1 -C 6 ) -alkyl
  • R 5 is hydrogen or (C 1 -C 4 ) -alkyl
  • R ' is acetoxy, acetamido, methoxycarbonyl or (C-3-C6) -cycloalkyl, n is 0, 1 or 2, s is 0, 1, 2 or 3,
  • L represents a bridge selected from the group consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A1, A12, A13, A14, A17, A25, A26, A27, A28, A29 , A30, A31, A32, A33, A34, A35, A36, A37, A38, A41, 49, 50, 51, 53, 55, 57, 59, 61, 62, 72, 13, 14, 14, 14, 14, 144, ⁇ 145, ⁇ 146, ⁇ 147, ⁇ 148, ⁇ 149, ⁇ 150, ⁇ 151, ⁇ 157, ⁇ 58, ⁇ 168, ⁇ 274, ⁇ 275, ⁇ 276, ⁇ 277, ⁇ 278, ⁇ 279, ⁇ 280, ⁇ 281, ⁇ 282, ⁇ 283, ⁇ 284, ⁇ 285, ⁇ 286, ⁇ 287, ⁇ 363 , ⁇ 364, ⁇ 365, ⁇ 366, ⁇ 367, ⁇ 368,
  • R 7 , R 8 , R 12 , R 13 , R 22 and R 23 are each independently
  • R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 are each independently hydrogen, halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) Haloalkyl or (C 1 -C 4) -alkoxy, or two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 form together with the carbon atom, to which they are attached, a carbonyl group or a
  • Oxime of the formula C NOR 1 or in each case two geminaie R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 is an acetal of the formula -0- (C 2 -C4) -alkylene-0-,
  • R 11 , R 18 , R 19 , R 26 and R 27 are each independently hydrogen or (Ci-Cr-alkyl, wherein the (Ci-Ce) alkyl group by s radicals from the group
  • X is nitro, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, chiorofluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, heptafluoroisopropyl, cyclopropyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, Methoxyethoxymethyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl,
  • W is hydrogen, chlorine or methyl
  • R is hydrogen
  • R x represents methyl, ethyl, n-propyl, prop-2-en-1-yl, methoxyethyl, ethoxyethyl or methoxyethoxyethyl
  • R Y is methyl, ethyl, n-propyl, chlorine or amino
  • R z is methyl, ethyl, n-propyl or methoxymethyl.
  • L denotes a bridge selected from the group consisting of A1, A2, A4, A5, A6, A7, A8, A25, A26, A28, A29, A30, A31, A32, A49, A50, A51, A53, A55, A57, A59, A61, A139, A140, A141, A142, A143, A145, A146, A147, A148, A149, A150, A274, A275, A278, A279, A280, A281, A282, A283, A284, A285, A286, A363, A364, A365, A366, A367, A368, A369, A370, A371, A372 and A373,
  • R 7 , R 8 , R 12 , R 13 , R 22 and R 23 are each independently
  • R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 are each independently hydrogen, halogen, methyl, methoxy, ethoxy or two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 together with the carbon atom to which they are attached form a carbonyl group or a
  • Oxime of formula C NOR 1 or two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 is an acetal of the formula -0- (CH 2 ) 2-0-,
  • R 1 is hydrogen, methyl or ethyl
  • R 11 , R 19 , R 26 and R 27 are each independently hydrogen or methyl
  • R 28 , R 29 , R 30 and R 31 independently of one another are each hydrogen, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl,
  • Chlorodifluoromethyl dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, Heptafluoroisopropyl, cyclopropyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxyethoxymethyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl.
  • the substituents and symbols unless otherwise defined, have the same meaning as described for formula (I).
  • dehydrating reagents commonly used for amidation reactions such as B. 1, 1 'carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 2,4,6-tripropyl-1, 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc. are used.
  • CDI 1, 1 'carbonyldiimidazole
  • DCC dicyclohexyl carbodiimide
  • T3P 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide
  • alkylating agents such as. B. alkyl halides, sulfonates or dialkyl sulfates can be used in the presence of a base.
  • 5-amino-1H-tetrazoles of the formula (III) are either commercially available or can be prepared analogously to methods known from the literature.
  • substituted 5-aminotetrazoles can be prepared from amino-tetrazole by the method described in Journal of the American Chemical Society (1954), 76, 923-924:
  • X represents a leaving group such as iodine.
  • the 5-amino-1H-triazoles of the formula (III) are either commercially available or can be prepared analogously to methods known from the literature.
  • substituted 5-aminotriazoles can be prepared from aminotriazole according to the method described in Zeitschrift fur Chemie (1990), 30 (12), 436-437:
  • X represents a leaving group such as iodine.
  • Substituted 5-aminotriazoles can also be synthesized, for example, as described in Chemische Berichte (1964), 97 (2), 396-404:
  • Substituted 5-aminotriazoles can also be used, for example, as in Angewandte Chemie
  • the 4-amino-1, 2,5-oxadiazoles of the formula (VI) are either commercially available or known or can be prepared analogously to methods known from the literature.
  • 3-alkyl-4-amino-1,2,5-oxadiazoles can be prepared according to the method described in Russian
  • 3-aryl-4-amino-1, 2,5-oxadiazoles can be synthesized as described in Russian Chemical Bulletin, 54 (4), 1057-1059, (2005) or Indian Journal of Chemistry, Section B:
  • 3-Amino-4-halo-1, 2,5-oxadiazoles can be prepared, for example, from the commercially available 3,4-diamino-1, 2.5 by the method described in Heteroatom Chemistry 15 (3), 199-207 (2004) Oxadiazole be prepared by a Sandmeyer reaction:
  • Nucleophilic radicals R Y can be found in Journal of Chemica! Research, Synopses, (6), 190, 1985 or in or Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, (9), 2086-8, 1986 or in Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya), 53 (3 ), 596-614, 2004, by substitution of the leaving group L in 3-amino-1, 2,5-oxadiazoles.
  • L stands for a leaving group such. Chlorine, bromine, iodine, mesyloxy, tosyloxy, trifluorosulfonyloxy etc.
  • dehydrating reagents commonly used for amidation reactions such as B. 1, 1 'carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 2,4,6-tripropyl-1, 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc. are used.
  • CDI 1, 1 'carbonyldiimidazole
  • DCC dicyclohexyl carbodiimide
  • T3P 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide
  • the compound of formula VIII employed in scheme 8 can be prepared by reacting an acyl isothiocyanate of formula X with a hydrazide of formula IX according to the method described in Synth. Commun. 25 (12), 1885-1892 (1995).
  • dehydrating reagents commonly used for amidation reactions such as B. 1, 1 'carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 2,4,6-tripropyl-1, 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc. are used.
  • CDI 1, 1 'carbonyldiimidazole
  • DCC dicyclohexyl carbodiimide
  • T3P 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide
  • the amines of the formula (XII) are either commercially available or known in the literature or can, for example, by the method described in Scheme 13 by base-catalyzed alkylation or by reductive alkylation or by the method described in Scheme 14 by nucleophilic substitution of a leaving group L such as chlorine Amine R-NH2 can be produced.
  • the listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed.
  • This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots.
  • Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.
  • the implementation of single or multiple synthetic steps can be supported by the use of polymer-supported reagents / Scavanger resins.
  • Synthesis methods allow a number of protocols known from the literature, which in turn can be carried out manually or automatically.
  • the reactions can be carried out, for example, by means of IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
  • the preparation according to the methods described herein provides compounds of formula (I) and their salts in the form of substance collections called libraries.
  • the present invention also provides libraries containing at least two compounds of formula (I) and their salts.
  • the compounds of the formula (I) according to the invention (and / or their salts), together referred to as "compounds according to the invention", have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants
  • the present invention therefore also relates to a method for controlling undesirable plants or regulating the growth of plants, preferably in plant crops, wherein one or more of the plants according to the invention are plants which are expectorant from rhizomes, rhizomes or other permanent organs
  • Compound (s) on the plants e.g., weeds such as mono- or dicotyledons
  • the compounds according to the invention can be applied, for example, in pre-sowing (optionally also by incorporation into the soil), pre-emergence or postemergence process.
  • some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species.
  • the compounds according to the invention are applied to the surface of the earth prior to germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then stop their growth and finally die after three to four weeks
  • Ipomoea Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the genera Allium, Pineapple, Asparagus, Avena,
  • Crops such as agricultural crops or ornamental plantings.
  • Influence of phytonutrients and harvest relief e.g. be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, since, for example, storage formation can thereby be reduced or completely prevented.
  • the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example, by resistance to certain pesticides, especially certain herbicides, resistance to Plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special special traits for example, by resistance to certain pesticides, especially certain herbicides, resistance to Plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • transgenic cultures Preferred with respect to transgenic cultures is the use of the compounds of the invention in economically important transgenic crops of useful and
  • Ornamental plants z.
  • cereals such as wheat, barley, rye, oats, millet, rice and corn or cultures of sugar beet, cotton, soybeans, rapeseed, potato, tomato, pea and other vegetables.
  • the compounds of the invention can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or
  • the application of the compounds of the invention or their salts in economically important transgenic crops of useful and ornamental plants eg.
  • cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
  • the compounds according to the invention can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • Glufosinate see, for example, EP-A-0242236, EP-A-242246) or glyphosate
  • transgenic crops characterized by a combination z.
  • nucleic acid molecules can be used in any genetic manipulations.
  • nucleic acid molecules can be used in any genetic manipulations.
  • Plasmids are introduced which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added.
  • adapters or linkers can be attached to the fragments be, see, for. Sambrook et al., 1989, Molecular Cioning, A Laboratory Manual, 2nd Ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996
  • the production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one
  • Cosuppressions canes or the expression of at least one appropriately engineered ribozyme that specifically cleaves transcripts of the above gene product.
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known in the art (see, for example, Braun et al., EMBO J. 1 1 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106). Expression of the nucleic acid molecules can also be found in the
  • Organelles of the plant cells take place.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
  • transgenic plants are available, the altered properties by
  • the compounds of the invention can be used in transgenic cultures which are resistant to growth factors, such as. B. Dicamba or against
  • Herbicides containing essential plant enzymes e.g. As acetolactate synthases (ALS), EPSP synthases, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthase
  • HPPD hydroxyphenylpyruvate dioxygenases
  • Harmful plants often have effects that are specific for application in the particular transgenic culture, such as altered or specially extended weed spectrum that can be controlled
  • the invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic
  • the compounds of the invention may be in the form of wettable powders
  • the invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.
  • the compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), Dusts (DP), mordants, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG),
  • WP wettable powder
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • EW emulsions
  • SC suspension concentrates
  • the necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are, for example
  • Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance, also contain ionic and / or nonionic surfactants (wetting agents, dispersants) other than a diluent or inert substance, for example polyoxyethylated alkylphenols.
  • the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are made by dissolving the active ingredient in one
  • organic solvents e.g. Butanol, cyclohexanone, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • emulsifiers which can be used are: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as e.g. Sorbitan fatty acid esters or
  • Polyoxethylenesorbitanester such. Polyoxyethylene. Dusts are obtained by milling the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solids e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. upstairs with the others
  • Emulsions e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, as described e.g. listed above for the other formulation types.
  • EW Oil-in-water emulsions
  • Granules can either be adsorbed by atomizing the active ingredient, granulated inert material or by applying active substance concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carriers such as sand, Kaoiinite or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
  • adhesives for example polyvinyl alcohol, sodium polyacrylate or mineral oils
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
  • the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients. at
  • the active substance concentration can be about 1 to 90,
  • Dust-like formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which
  • Granulation aids, fillers, etc. are used. In the water
  • the content of active ingredient is for example between 1 and 95 wt .-%, preferably between 10 and 80 wt .-%.
  • the active substance formulations mentioned optionally contain the customary adhesive, wetting, dispersing, emulsifying, penetrating, preserving,
  • the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dusty preparations, ground or spreading granules and sprayable
  • the type of herbicide used u.a. varies the required application rate of the compounds of formula (I). It can vary within wide limits, e.g. between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 0.005 and 750 g / ha.
  • Step 1 Synthesis of 7-methyl-1-benzothiophene-6-carboxylic acid methyl ester
  • Step 3 Synthesis of 7-methyl-N- (1-methyl-1H-tetrazol-5-yl) -1-benzothiophene-6-carboxamide
  • n-Pr n-propyl
  • c-Pr c-propyl
  • Ph phenyl
  • Table 2 Compounds of the invention of the general formula (I) wherein Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A30, wherein the radicals R 7 and R 8 are both hydrogen
  • Table 1 1 Compounds of the invention of the general formula (I), wherein Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A32, wherein the radicals R 7 and R 8 are both hydrogen
  • R x is an ethyl group and R is hydrogen and L is the bridge A8, wherein the radical R 7 is hydrogen
  • R Y is a methyl group and R is hydrogen and L is the bridge A8, wherein the radical R 7 is hydrogen
  • R z represent a methyl group and R is hydrogen and L is the bridge A8, where R 7 is hydrogen
  • Table 20 Compounds of the invention of the general formula (I) wherein Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A363, wherein the radicals R 28 , R 29 , R 30 and R 31 is
  • Table 25 Compounds according to the invention of the general formula (I) in which Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A364 in which R 29 , R 30 and R 31 are hydrogen
  • Table 26 Compounds according to the invention of the general formula (I) in which Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A364 in which the radicals R 29 , R 30 and R 31 are hydrogen
  • Table 29 Compounds according to the invention of the general formula (I) in which Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A364, where R 29 , R 30 and R 31 are hydrogen
  • Table 31 Compounds of the invention of the general formula (I) wherein Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A365, wherein the radicals R 28 , R 30 and R 31 are hydrogen
  • Table 32 Compounds of the invention of the general formula (I) in which Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A365, in which the radicals R 28 , R 30 and R 31 are hydrogen
  • Table 33 Compounds of the invention of the general formula (I) in which Q is Q1, R x is an n-propyl group and R is hydrogen and L is the bridge A365 in which the radicals R 28 , R 30 and R 31 are hydrogen
  • Bridge A365 means where R 28 , R 30 and R 31 are hydrogen
  • Table 35 Compounds of the invention of the general formula (I) in which Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A365 in which the radicals R 28 , R 30 and R 31 are hydrogen
  • Table 37 Compounds of the invention of the general formula (I) in which Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A366, in which R 28 , R 29 and R 31 are hydrogen
  • Table 38 Compounds according to the invention of the general formula (I) in which Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A366 in which the radicals R 28 , R 29 and R 31 are hydrogen
  • Table 40 Compounds of the invention of the general formula (I) wherein Q is Q 2, R x is a methyl group and R is hydrogen and L is the bridge A366 in which R 28 , R 29 and R 31 are hydrogen
  • Table 43 Compounds of the invention of the general formula (I) in which Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A367, in which R 28 , R 29 and R 30 are hydrogen
  • Table 44 Compounds of the invention of the general formula (I) in which Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A367, in which the radicals R 28 , R 29 and R 30 are hydrogen
  • Table 46 Compounds of the invention of the general formula (I) in which Q is Q 2, R x is a methyl group and R is hydrogen and L is the bridge A367, in which R 28 , R 29 and R 30 are hydrogen
  • Table 55 Compounds of the invention of the general formula (I) in the form of the sodium salts, wherein Q is Q1, R * is a methyl group and L is the bridge A366, wherein the radicals R 28 , R 29 and R 31 are hydrogen
  • Table 57 Compounds of the invention of the general formula (I) in which Q is Q1 and R is hydrogen and L is the bridge A6, in which the radicals R 7 and R 8 are hydrogen
  • Y is a methyl group and R is hydrogen and L is the
  • Table 61 Compounds of the invention of the general formula (I) wherein Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A282, wherein the radicals R 12 , R 13 , R 14 and R 15 is
  • Table 62 Compounds of the general formula (I) according to the invention wherein Q is Q1, R x is an ethyl group, and R is hydrogen and L the bridge A282 means, in which the radicals R 12, R 13, R 14 and R 15 are hydrogen
  • Table 63 Compounds of the invention of the general formula (I) in which Q is Q1, R x is an n-propyl group and R is hydrogen and L is the bridge A282 in which the radicals R 12 , R 13 , R 14 and R 15
  • Q is Q1
  • R x is an n-propyl group and R is hydrogen
  • L is the bridge A282 in which the radicals R 12 , R 13 , R 14 and R 15
  • Table 64 Compounds of the invention of the general formula (I) wherein Q is Q 2, R x is a methyl group and R is hydrogen and L is the bridge A282, wherein the radicals R 12 , R 13 , R 14 and R 15 are
  • Table 65 Compounds of the invention of the general formula (I) wherein Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A282 in which the radicals R 12 , R 13 , R 14 and R 15 are
  • Table 68 Compounds of the general formula (I) according to the invention wherein Q is Q1, R x is an ethyl group, and R is hydrogen and L the bridge A286 means, in which the radicals R 12, R 13, R 14 and R 15 are hydrogen

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Abstract

The invention relates to bicycloaryl carboxylic acid amides of general formula (I), used as herbicides. In said formula (I), X and W represent groups such as hydrogen, organic groups such as alkyl, and other groups such as halogen. Q represents triazolyl, tetrazolyl or oxadiazolyl.

Description

Herbizid wirksame Bicycloarylcarbonsäureamide  Herbicidally active bicycloarylcarboxylic acid amides
Beschreibung description
Die Erfindung betrifft das technische Gebiet der Herbizide, insbesondere das der Herbizide zur selektiven Bekämpfung von Unkräutern und Ungräsern in The invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and weeds in
Nutzpflanzenkulturen. Crops of useful plants.
Die prioritätsältere nicht vorveröffentlichte europäische Patentanmeldung The prioritized non-prepublished European patent application
EP 1 1158258 offenbart N-(Tetrazol-5-yl)-, N-(Triazol-5-yl)- und N-(1 ,2,5-Oxadiazol-3- yl)bicycloarylcarbonsäureamide und ihre Verwendung als Herbizide. Allerdings zeigen diese Verbindungen nicht immer eine ausreichende Wirkung gegen Schadpflanzen und/oder sie sind zum Teil nicht ausreichend verträglich mit einigen wichtigen EP 1 1158258 discloses N- (tetrazol-5-yl), N- (triazol-5-yl) and N- (1, 2,5-oxadiazol-3-yl) bicycloarylcarboxamides and their use as herbicides. However, these compounds do not always show a sufficient effect against harmful plants and / or they are sometimes not sufficiently compatible with some important ones
Kulturpflanzen, wie Getreidearten, Mais oder Reis. Crops such as cereals, corn or rice.
Es wurde nun gefunden, dass N-(Tetrazol-5-yl)-, N-(Triazol-5-yl)-, N-(1 ,2,5-Oxadiazol- 3-yl)- und N-(1 ,3,4-Oxadiazol-2-yl)bicycloarylcarbonsäureamide, die sich von den aus dem Stand der Technik bekannten Verbindungen im Wesentlichen dadurch It has now been found that N- (tetrazol-5-yl), N- (triazol-5-yl), N- (1, 2,5-oxadiazol-3-yl) - and N- (1, 3,4-oxadiazol-2-yl) bicycloarylcarboxylic acid amides substantially different from those known in the art
unterscheiden, dass der an den Phenylring ankondensierte Ring ungesättigt ist, als Herbizide besonders gut geeignet sind. Ein Gegenstand der vorliegenden Erfindung sind somit N-(Tetrazol-5-yl)-, N-(Triazol-5- yl)-, N-(1 ,2,5-Oxadiazol-3-yl)- und N-(1 ,3,4-Oxadiazol-2- yl)bicycloarylcarbonsäureamide der Formel (I) oder deren Salze distinguish that the ring fused to the phenyl ring is unsaturated, as herbicides are particularly well suited. An object of the present invention are thus N- (tetrazol-5-yl) -, N- (triazol-5-yl) -, N- (1, 2,5-oxadiazol-3-yl) - and N- (1 , 3,4-oxadiazol-2-yl) bicycloarylcarboxamides of the formula (I) or salts thereof
die Symbole und Indizes folgende Bedeutungen haben bedeutet einen Rest Q1 , Q2, Q3 oder Q4, the symbols and indices have the following meanings means a remainder Q1, Q2, Q3 or Q4,
(Q1 ) (Q2) (Q3) (Q4)  (Q1) (Q2) (Q3) (Q4)
X bedeutet Nitro, Halogen, Cyano, Rhodano, (d-Ce -Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3- C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkenyl, Halogen-(C3-C6)- cycloalkenyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkenyl-(Ci-C6)-alkyl, R1(O)C, R1(R1ON=)C, RO(O)C, (R1)2N(O)C, R1(RO)N(O)C, (R1)2N(R1)N(O)C, X is nitro, halo, cyano, rhodano, (d-Ce alkyl, halo (Ci-C6) alkyl, (C 2 -C 6 ) alkenyl, halo (C 2 -C 6 ) alkenyl, (C 2 -C 6) alkynyl, halo (C 3 -C 6) -alkynyl, (C 3 - C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (C 3 -C 6) - cycloalkenyl, halo (C 3 -C 6) - cycloalkenyl, (C 3 -C 6) -cycloalkyl- (Ci-C6) alkyl, halo (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, (C 3 -C 6) cycloalkenyl (Ci-C 6) alkyl, halo (C 3 -C 6) cycloalkenyl (Ci-C 6) alkyl, R 1 (O) C R 1 (R 1 ON =) C, RO (O) C, (R 1 ) 2 N (O) C, R 1 (RO) N (O) C, (R 1 ) 2 N (R 1 ) N ( O) C,
R1(O)C(R1)N(O)C, R2O(O)C(R1)N(O)C, (R1)2N(O)C(R1)N(O)C, R2(O)2S(R1)N(O)C, R1O(O)2S(R1)N(O)C, (R1)2N(O)2S(R1)N(O)C, RO, R1(O)CO, R2(O)2SO, R2O(O)CO, (R1)2N(O)CO, (R1)2N, R1(O)C(R1)N, R2(O)2S(R1)N, R2O(O)C(R1)N, (R1)2N(O)C(R1)N, R1O(O)2S(R1)N, (R1)2N(O)2S(R1)N, R2(O)nS, R1O(O)2S, (R1)2N(O)2S, R 1 (O) C (R 1 ) N (O) C, R 2 O (O) C (R 1 ) N (O) C, (R 1 ) 2 N (O) C (R 1 ) N (O ) C, R 2 (O) 2 S (R 1 ) N (O) C, R 1 O (O) 2 S (R 1 ) N (O) C, (R 1 ) 2 N (O) 2 S ( R 1 ) N (O) C, RO, R 1 (O) CO, R 2 (O) 2 SO, R 2 O (O) CO, (R 1 ) 2 N (O) CO, (R 1 ) 2 N, R 1 (O) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N, R 2 O (O) C (R 1 ) N, (R 1 ) 2 N (O) C (R 1 ) N, R 1 O (O) 2 S (R 1 ) N, (R 1 ) 2 N (O) 2 S (R 1 ) N, R 2 (O) n S, R 1 O (O ) 2 S, (R 1 ) 2 N (O) 2 S,
R1(O)C(R1)N(O)2S, R2O(O)C(R1)N(O)2S, (R1)2N(O)C(R1)N(O)2S, (R5O)2(O)P, R1(O)C- (Ci-C6)-Alkyl, R1O(O)C-(Ci-C6)-Alkyl, (R1)2N(O)C-(Ci-C6)-Alkyl, (R1O)(R1)N(O)C-(Ci- C6)-Alkyl, (R1)2N(R1)N(O)C-(Ci-C6)-Alkyl, R1(O)C(R1)N(O)C-(Ci-C6)-Alkyl, R 1 (O) C (R 1 ) N (O) 2 S, R 2 O (O) C (R 1 ) N (O) 2 S, (R 1 ) 2 N (O) C (R 1 ) N (O) 2 S, (R 5 O) 2 (O) P, R 1 (O) C- (C 1 -C 6 ) -alkyl, R 1 O (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) C- (C 1 -C 6 ) -alkyl, (R 1 O) (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, R 1 (O) C (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl,
R2O(O)C(R1)N(O)C-(Ci-C6)-Alkyl, (R1)2N(O)C(R1)N(O)C-(Ci-C6)-Alkyl, R 2 O (O) C (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) C (R 1 ) N (O) C- (Ci-C 6 ) -alkyl,
R2(O)2S(R1)N(O)C-(Ci-C6)-Alkyl, R1O(O)2S(R1)N(O)C-(Ci-C6)-Alkyl, R 2 (O) 2 S (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, R 1 O (O) 2 S (R 1 ) N (O) C- (C 1 -C 6 ) alkyl,
(R1)2N(O)2S(R1)N(O)C-(Ci-C6)-Alkyl, NC-(Ci-C6)-Alkyl, R1O-(Ci-C6)-Alkyl, R1(O)CO- (Ci-C6)-Alkyl, R2(O)2SO-(Ci-C6)-Alkyl, R2O(O)CO-(Ci-C6)-Alkyl, (R1)2N(O)CO-(Ci-C6)- Alkyl, (R1)2N-(Ci-C6)-Alkyl, R1(O)C(R1)N-(Ci-C6)-Alkyl, R2(O)2S(R1)N-(Ci-C6)-Alkyl, R2O(O)C(R1)N-(Ci-C6)-Alkyl, (R1)2N(O)C(R1)N-(Ci-C6)-Alkyl, R1O(O)2S(R1)N-(Ci-C6)- Alkyl, (R1)2N(O)2S(R1)N-(Ci-C6)-Alkyl, R2(O)nS-(Ci-C6)-Alkyl, R1O(O)2S-(Ci-C6)-Alkyl, (R1)2N(O)2S-(Ci-C6)-Alkyl, R1(O)C(R1)N(O)2S-(Ci-C6)-Alkyl, R2O(O)C(R1)N(O)2S-(Ci- C6)-Alkyl, (R1)2N(O)C(R1)N(O)2S-(Ci-C6)-Alkyl, (R5O)2(O)P-(Ci-C6)-Alkyl, Phenyl, Heteroaryl, Heterocyclyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl- (Ci-Ce)-alkyl, wobei die sechs letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, Cyano, Rhodano, (Ci-C6)-Alkyl, Halogen-(d- C6)-alkyl, (C3-C6)-Cycloalkyl, R1O(O)C, (R1)2N(O)C, R1O, (R1)2N, R2(O)nS, R1O(O)2S, (R1)2N(O)2S und R1O-(Ci-C6)-Alkyl substituiert sind, und wobei Heterocyclyl n (R 1) 2 N (O) 2 S (R 1) N (O) C- (Ci-C 6) -alkyl, NC (Ci-C 6) alkyl, R 1 O- (Ci-C 6 ) Alkyl, R 1 (O) CO- (C 1 -C 6 ) -alkyl, R 2 (O) 2 SO- (C 1 -C 6 ) -alkyl, R 2 O (O) CO- (C 1 -C 6 ) alkyl, (R 1) 2 N (O) CO- (Ci-C 6) - alkyl, (R 1) 2 N- (Ci-C 6) alkyl, R 1 (O) C (R 1) N- (Ci-C 6) alkyl, R 2 (O) 2 S (R 1) N- (Ci-C 6) alkyl, R 2 O (O) C (R 1) N- (Ci-C 6 ) -alkyl, (R 1 ) 2 N (O) C (R 1 ) N- (C 1 -C 6 ) -alkyl, R 1 O (O) 2 S (R 1 ) N- (C 1 -C 6 ) - alkyl, (R 1 ) 2 N (O) 2 S (R 1 ) N - (C 1 -C 6 ) -alkyl, R 2 (O) n S- (C 1 -C 6 ) -alkyl, R 1 O ( O) 2 S- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) 2 S- (C 1 -C 6 ) -alkyl, R 1 (O) C (R 1 ) N (O) 2 S- (C 1 -C 6 ) -alkyl, R 2 O (O) C (R 1 ) N (O) 2 S- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) C (R 1 ) N (O) 2 S- (C 1 -C 6 ) -alkyl, (R 5 O) 2 (O) P- (C 1 -C 6 ) -alkyl, phenyl, heteroaryl, heterocyclyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl- (Ci-C6) -alkyl, heterocyclyl (Ci-Ce) -alkyl, wherein the six last mentioned radicals in each case by s radicals from the group consisting of nitro, halogen, cyano, Rhodano, (Ci-C6 ) alkyl, halo (d- C6) alkyl, (C 3 -C 6) -Cycl oalkyl, R 1 O (O) C, (R 1 ) 2 N (O) C, R 1 O, (R 1 ) 2 N, R 2 (O) n S, R 1 O (O) 2 S, ( R 1 ) 2 N (O) 2 S and R 1 O- (C 1 -C 6 ) -alkyl, and wherein heterocyclyl n
Oxogruppen trägt, W bedeutet Wasserstoff, Halogen, Nitro, Cyano, Rhodano, (Ci-CeJ-Alkyl, Halogen- (Ci-Ce)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3- C6)-alkinyl, (C3-C/)-Cycloalkyl, Halogen-(C3-C/)-cycloalkyl, (Ci-C6)-Alkoxy, Halogen- (Ci-Ce)-alkoxy, (Ci-C6)-Alkyl-(O)nS-, (Ci-C6)-Ha!ogenaikyl-(O)nS-, (Ci-C6)-Alkoxy-(Ci- C4)-alkyl, (Ci-C6)-Alkoxy-(Ci-C4)-halogenalkyl, R1(O)C, R1(RON=)C, R1O(O)C, (R1)2N, R1(O)C(R1)N oder R2(O)2S(R1)N, Wearing oxo groups, W is hydrogen, halogen, nitro, cyano, rhodano, (C 1 -C 6 -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogeno (C 2 -C 6 ) -alkenyl, (C2-C6) alkynyl, halo (C 3 - C 6) -alkynyl, (C 3 -C /) - cycloalkyl, halo (C 3 -C /) - cycloalkyl, (Ci-C 6) - Alkoxy, halogen- (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkyl- (O) n S-, (C 1 -C 6 ) -haloalkyl (O) nS-, (C 1 -C 6) ) -Alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -haloalkyl, R 1 (O) C, R 1 (RON =) C, R 1 O ( O) C, (R 1 ) 2 N, R 1 (O) C (R 1 ) N or R 2 (O) 2 S (R 1 ) N,
R bedeutet Wasserstoff, (Ci-C6)-Alkyl, Ha!ogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-CycSoalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)- cycloalkyl-(Ci-C6)-alkyl, R1(O)C-(Ci-C6)-Alkyl, R1O(O)C-(Ci-C6)-Alkyl, (R1)2N(O)C-(Ci- C6)-A!kyi, NC-(Ci-C6)-Alkyl, R1O-(Ci-C6)-Alkyl, R1(O)CO-(Ci-C6)-Alkyl, R2(O)2SO-(Ci- C6)-Alkyl, (R1)2N-(Ci-C6)-Alkyl, R1(O)C(R1)N-(Ci-C6)-Alky!, R2(O)2S(R1)N-(Ci-C6)-Aikyl, R2(O)nS-(Ci-C6)-Alkyl, R1O(O)2S-(Ci-C6)-Alkyl, (R1)2N(O)2S-(Ci-C6)-Alkyl, R1(O)C, R1O(O)C, (R1)2N(O)C, RO, (R1)2N, R2O(O)C(R1)N, (R1)2N(O)C(R1)N, R2(O)2S, oder jeweils durch s Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Nitro, Trifluormethyl und Halogen substituiertes Benzyl, Rx bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2- Ce)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, wobei die sechs vorstehend genannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Cyano, (R6)3Si, (R5O)2(O)P, R2(O)„S, (R1)2N, R1O, R1(O)C, R1O(O)C, R1(O)CO, R2O(O)CO, R1(O)C(R1)N, R2(O)2S(R1)N, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocyclyl und Phenyl substituiert sind, wobei die vier letztgenannten Reste durch s Reste aus der Gruppe bestehend aus (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-Ce)- alkoxy und Halogen substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, oder R is hydrogen, (Ci-C 6) -alkyl, Ha! Ogen (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C2-C6) alkenyl, (C 2 -C 6 ) alkynyl, halo (C 3 -C 6 ) alkynyl, (C 3 -C 6 ) cycloalkyl, halo (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) -CycSoalkyl - (Ci-C6) alkyl, halo (C 3 -C 6) - cycloalkyl- (Ci-C 6) alkyl, R 1 (O) C- (Ci-C 6) alkyl, R 1 O (O) C- (Ci-C 6) -alkyl, (R 1) 2 N (O) C- (Ci- C 6) -A! kyi, NC (Ci-C 6) alkyl, R 1 O - (Ci-C 6) alkyl, R 1 (O) CO- (Ci-C 6) alkyl, R 2 (O) 2 SO- (Ci- C6) alkyl, (R 1) 2 N- (Ci-C 6) alkyl, R 1 (O) C (R 1) N- (Ci-C 6) -Alky !, R 2 (O) 2 S (R 1) N- (Ci-C 6) -Alkyl, R 2 (O) n S- (C 1 -C 6 ) -alkyl, R 1 O (O) 2 S- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) 2S- ( C 1 -C 6 ) -alkyl, R 1 (O) C, R 1 O (O) C, (R 1 ) 2 N (O) C, RO, (R 1 ) 2 N, R 2 O (O) C (R 1 ) N, (R 1 ) 2 N (O) C (R 1 ) N, R 2 (O) 2 S, or in each case by s radicals from the group consisting of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen substituted benzyl, R x (Ci-C 6) alkyl, halo (Ci-C 6) alkyl means (C 2 -C 6) -Alke nyl, halo (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkynyl, halogeno (C 3 -C 6) -alkynyl, where the six radicals mentioned above are in each case represented by s radicals from the group consisting of nitro, cyano , (R 6 ) 3 Si, (R 5 O) 2 (O) P, R 2 (O) "S, (R 1 ) 2 N, R 1 O, R 1 (O) C, R 1 O (O ) C, R 1 (O) CO, R 2 O (O) CO, R 1 (O) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N, (C 3 -C 6 ) -Cycloalkyl, heteroaryl, heterocyclyl and phenyl are substituted, wherein the four latter radicals by s radicals from the group consisting of (Ci-C 6 ) alkyl, halogeno (Ci-C 6 ) alkyl, (Ci-C 6 ) Alkoxy, halo (C 1 -C 6) alkoxy and halogen, and wherein heterocyclyl carries n oxo groups, or
Rx bedeutet (C3-C )-Cycloalkyl, Heteroaryl, Heterocyclyl oder Phenyl, wobei die vier vorstehend genannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl,R x is (C 3 -C) -cycloalkyl, heteroaryl, heterocyclyl or phenyl, where the four radicals mentioned above are in each case represented by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogen (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl,
(Ci-Ce)-Alkyl- S(O)n, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci- C4)-alkyl substituiert sind, RY bedeutet Wasserstoff, (Ci-C6)-A!kyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-a!kenyi, (C2-C6)-Alkiny!, Halogen-(C3-C6)-alkinyl, (Cs-C/J-Cycloalkyl,(C 1 -C 6 ) -alkyl- S (O) n , (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) - alkyl are substituted, R Y is hydrogen, (Ci-C 6) -A! Kyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) -a! Kenyi , (C2-C6) -Alkiny !, halo (C 3 -C 6) -alkynyl, (Cs-C / J-cycloalkyl,
(d-CeJ-Alkoxy, Halogen-(Ci-C6)-alkoxy, (C2-C6)-Alkenyloxy, (C2-C6)-Alkinyloxy, Cyano, Nitro, Methylsulfenyl, MethylsuSfinyl, Methylsulfonyl, Acetylamino, (d-CeJ-alkoxy, halo (C 1 -C 6) -alkoxy, (C 2 -C 6) -alkenyloxy, (C 2 -C 6) -alkynyloxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino,
Benzoylamino, Methoxycarbonyl, Ethoxycarbonyl, Methoxycarbonylmethyl, Benzoylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl,
Ethoxycarbonylmethyl, Benzoyl, Methylcarbonyl, Piperidinylcarbonyl,  Ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl,
TrifluormethyScarbonyl, Halogen, Amino, Aminocarbonyl, Methylaminocarbonyl, Dimethylaminocarbonyl, Methoxymethyl, Trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl,
oder jeweils durch s Reste aus der Gruppe bestehend aus (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (Ci-CeJ-Alkoxy, Halogen-(Ci-C6)-alkoxy und Halogen substituiertes Heteroaryi, Heterocyclyl oder Phenyl, und wobei Heterocyclyl n Oxogruppen trägt, or in each case by s radicals from the group consisting of (C 1 -C 6) -alkyl, halogeno (C 1 -C 6) -alkyl, (C 1 -C 6 -alkoxy, halogeno (C 1 -C 6) -alkoxy and halogen-substituted heteroaryl, heterocyclyl or phenyl, and wherein heterocyclyl carries n oxo groups,
Rz bedeutet Wasserstoff, (Ci-C6)-Alkyl, R10-(Ci-C6)-Alkyl, R'CH2, (C3-C/)- Cycloalkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)- Alkinyl, Halogen-(C3-C6)-alkinyl, R10, R1(H)N, Methoxycarbonyl, Ethoxycarbonyl,R z is hydrogen, (C 1 -C 6 ) -alkyl, R 1 0- (C 1 -C 6 ) -alkyl, R'CH 2 , (C 3 -C 6 ) -cycloalkyl, halogeno (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, halo (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, halo (C 3 -C 6 ) alkynyl, R 1 0 , R 1 (H) N, methoxycarbonyl, ethoxycarbonyl,
Methylcarbonyl, Dimethylamino, Trifluormethylcarbonyl, Acetylamino, Methylsulfenyl, Methylsulfinyl, Methylsulfonyl oder jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (Ci-C6)-Alkyl- S(0)n, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci- C4)-alkyl substituiertes Heteroaryi, Heterocyclyl, Benzyl oder Phenyl, wobei Methylcarbonyl, dimethylamino, trifluoromethylcarbonyl, acetylamino, methylsulfenyl, methylsulfinyl, methylsulfonyl or in each case by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, ( C 3 -C 6) -cycloalkyl, (Ci-C6) alkyl- S (0) n, (Ci-Ce) alkoxy, halo (Ci-C 6) alkoxy and (Ci-C 6) - Alkoxy- (C 1 -C 4) -alkyl-substituted heteroaryl, heterocyclyl, benzyl or phenyl, wherein
Heterocyclyl n Oxogruppen trägt, Heterocyclyl carries n oxo groups,
R1 bedeutet Wasserstoff, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (Cs-CeJ-Cycloalkyl, (C3-C6)-Cycloalkenyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci- C6)-Alkyl-O-(Ci-C6)-alkyl, Cycloalkyl-(Ci-C6)-alkyl-O-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci- Ce)-alkyl, Heteroaryi, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, Phenyl-O-(Ci-C6)-alkyl, Heteroaryl-O-(Ci-C6)-alkyl, Heterocyclyl-O-(Ci-C6)-alkyl, Phenyl-N(R3)-(Ci-C6)-alkyl, Heteroaryl-N(R3)-(Ci-C6)-alkyl, Heterocyclyl-N(R3)-(Ci-C6)- alkyl, Phenyl-S(O)n-(Ci-C6)-alkyl, Heteroaryl-S(O)n-(Ci-C6)-alkyl, Heterocyclyl-S(O)n- (Ci-CeJ-alkyl, wobei die fünfzehn letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, Cyano, Rhodano, (Ci-C6)-Alkyl, Halogen-(Ci- C6)-alkyl, (C3-C6)-Cycloalkyl, R3O(O)C, (R3)2N(O)C, R3O, (R3)2N, R4(O)„S, R3O(O)2S, (R3)2N(0)2S und R30-(Ci-C6)-Alkyl substituiert sind, und wobei Heterocyclyl n R 1 represents hydrogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6 ) alkynyl, halo (C 3 -C 6 ) alkynyl, (Cs-CeJ-cycloalkyl, (C 3 -C 6 ) -cycloalkenyl, halo (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, cycloalkyl- (C 1 -C 6 ) -alkyl-O- (Ci C 6 ) alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl (C 1 -C 6 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6 ) -alkyl, phenyl-O- (C 1 -C 4 ) -alkyl, C 6 ) -alkyl, heteroaryl-O- (C 1 -C 6 ) -alkyl, heterocyclyl-O- (C 1 -C 6 ) -alkyl, phenyl-N (R 3 ) - (C 1 -C 6 ) -alkyl, heteroaryl -N (R 3) - (Ci-C 6) alkyl, heterocyclyl-N (R 3) - (Ci-C 6) - alkyl, phenyl-S (O) n - (Ci-C 6) alkyl, Heteroaryl-S (O) n - (C 1 -C 6 ) -alkyl, heterocyclyl-S (O) n - (C 1 -C 6 -alkyl, where the fifteen latter radicals are in each case represented by s radicals from the group consisting of nitro, halogen, Cyano, rhodano, (C 1 -C 6 ) -alkyl, halo (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, R 3 O (O) C, (R 3 ) 2 N (O) C, R 3 O, (R 3 ) 2 N, R 4 (O) "S, R 3 O (O) 2 S, (R 3 ) 2 N (O) 2 S and R 3 are 0- (C 1 -C 6 ) alkyl substituted, and wherein heterocyclyl n
Oxogruppen trägt, Wearing oxo groups,
R2 bedeutet (Ci-C6)-Alkyl, Haiogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyi, Halogen-(C2-C6)- alkenyl, (C2-C6)-Aikinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)-Cycloaikyl, (C3-C6)-R 2 is (Ci-C 6) -alkyl, Haiogen- (Ci-C 6) alkyl, (C 2 -C 6) -Alkenyi, halo (C 2 -C 6) - alkenyl, (C 2 -C 6) -Aikinyl, halo (C3-C6) -alkynyl, (C 3 -C 6) -Cycloaikyl, (C 3 -C 6) -
Cycloalkenyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-Ce)- Alkyl-0-(Ci-C6)-alkyl, Cycloalkyl-(Ci-C6)-alkyl-0-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)- alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, Phenyl-0-(Ci-C6)-alkyl, Heteroaryl-0-(Ci-C6)-alkyl, Heterocyclyl-0-(Ci-C6)-alkyl, Phenyl-N(R3)-(Ci-C6)-alkyl, Heteroaryl-N(R3)-(C1-C6)-alkyl, Heterocyclyl-N(R3)-(Ci-C6)- alkyl, Phenyl-S(0)n-(Ci-C6)-alkyl, Heteroaryl-S(0)n-(Ci-C6)-alkyl, Heterocyclyl-S(0), (Ci-Ce)-alkyl, wobei die fünfzehn letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, Cyano, Rhodano, (Ci-C6)-Alkyl, Halogen-(Ci- C6)-alkyl, (C3-C6)-Cycloalkyl, R30(0)C, (R3)2N(0)C, R 0, (R3)2N, R4(0)nS, R30(0)2S, (R3)2N(0)2S und R30-(Ci-C6)-Alkyl substituiert sind, und wobei Heterocyclyl n Cycloalkenyl, halo (C 3 -C 6) cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (Ci-Ce) - alkyl-0- (Ci-C 6) alkyl, Cycloalkyl- (C 1 -C 6 ) -alkyl-0- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl, heterocyclyl (C 1 -C 6 ) -alkyl, phenyl-O- (C 1 -C 6 ) -alkyl, heteroaryl-O- (C 1 -C 6 ) -alkyl, heterocyclyl-O- (C 1 -C 6 ) -alkyl, phenyl N (R 3) - (Ci-C 6) alkyl, heteroaryl-N (R 3) - (C 1 -C 6) alkyl, heterocyclyl-N (R 3) - (Ci-C 6) - alkyl, Phenyl-S (0) n - (C 1 -C 6 ) -alkyl, heteroaryl-S (O) n - (C 1 -C 6 ) -alkyl, heterocyclyl-S (0), (C 1 -C 6 ) -alkyl, where the fifteen last-mentioned radicals in each case by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (Ci-C6) alkyl, halo (Ci- C6) alkyl, (C 3 -C 6) -cycloalkyl, R 3 0 (0) C, (R 3 ) 2 N (O) C, R 0, (R 3 ) 2 N, R 4 (O) n S, R 3 0 (0) 2 S, (R 3 ) N 2 (0) 2 S and R 3 0- (Ci-C 6) alkyl substituted heterocyclyl and wherein n
Oxogruppen trägt, Wearing oxo groups,
R3 bedeutet Wasserstoff, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, (C2- C6)-Alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 3 represents hydrogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 - C 6) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
R4 bedeutet (Ci-Ce)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 4 is (Ci-Ce) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (C 3 -C 6) - Cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
R5 bedeutet Wasserstoff oder (Ci-C4)-Alkyl, R 5 is hydrogen or (C 1 -C 4 ) -alkyl,
R6 bedeutet (Ci-C4)-Alkyl, R 6 is (C 1 -C 4 ) -alkyl,
R' bedeutet Acetoxy, Acetamido, N-Methylacetamido, Benzoyloxy, Benzamido, N- Methylbenzamido, Methoxycarbonyl, Ethoxycarbonyl, Benzoyl, Methylcarbonyl, Piperidinylcarbonyl, Morpholinylcarbonyl, Trifluormethylcarbonyl, Aminocarbonyl,R 'denotes acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl,
Methylaminocarbonyi, Dimethyiaminocarbonyl, (C3-C6)-Cycloalkyl oder jeweils durch s Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl und Halogen substituiertes Heteroaryl oder Heterocyclyl, n bedeutet 0, 1 oder 2, m bedeutet 0, 1 , 2, 3 oder 4, s bedeutet 0, 1 , 2 oder 3, t bedeutet 0, 1 , 2, 3, 4 oder 5, Methylaminocarbonyi, dimethyiaminocarbonyl, (C 3 -C 6) -cycloalkyl or heteroaryl or heterocyclyl which is in each case substituted by s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen, n is 0, 1 or 2, m is 0, 1, 2, 3 or 4, s is 0, 1, 2 or 3, t is 0, 1, 2, 3, 4 or 5,
L bedeutet eine 3-, 4- oder 5-gliedrige ankondensierte, ungesättigte Brücke, deren Brückenatome aus t Kohlenstoffatomen und m Heteroatomen aus der Gruppe bestehend aus O, S und N bestehen. L is a 3-, 4- or 5-membered fused-on, unsaturated bridge whose bridge atoms consist of t carbon atoms and m heteroatoms from the group consisting of O, S and N.
In der Formel (I) und allen nachfolgenden Formeln können Alkylreste mit mehr als zwei Kohlenstoffatomen geradkettig oder verzweigt sein. Alkylreste 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. Analog bedeutet Alkenyl z.B. Allyl, 1 -Methylprop-2-en-1 -yl, In formula (I) and all subsequent formulas, alkyl radicals having more than two carbon atoms may be straight-chain or branched. Alkyl radicals 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. Analogously, alkenyl means e.g. Allyl, 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 und 1 -Methyl-but-2-en-1 -yl. Alkinyl bedeutet z.B. Propargyl, But-2-in-1 -yl, But-3-in-1 -yl, 1 -Methyl-but-3-in-1 -yl. Die Mehrfachbindung kann sich jeweils in beliebiger Position des ungesättigten Rests befinden. Cycloalkyl bedeutet ein carbocyclisches, gesättigtes Ringsystem mit drei bis sechs C-Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl. Analog bedeutet Cycloalkenyl eine monocyclische Alkenylgruppe mit drei bis sechs Kohlenstoffringgliedern, z.B. Cyclopropenyl, Cyclobutenyl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1 - Methyl-but-2-en-1-yl. Alkynyl means e.g. Propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl. The multiple bond can each be in any position of the unsaturated radical. Cycloalkyl means a carbocyclic saturated ring system having three to six C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl group having three to six carbon ring members, e.g. Cyclopropenyl, cyclobutenyl,
Cyclopentenyl und Cyclohexenyl, wobei sich die Doppelbindung an beliebiger Position befinden kann. Cyclopentenyl and cyclohexenyl, wherein the double bond may be in any position.
Halogen steht für Fluor, Chlor, Brom oder lod. Halogen is fluorine, chlorine, bromine or iodine.
Heterocyclyl bedeutet einen gesättigten, teilgesättigten oder vollständig ungesättigten cyclischen Rest, der 3 bis 6 Ringatome enthält, von denen 1 bis 4 aus der Gruppe bestehend aus Sauerstoff, Stickstoff und Schwefel stammen, und der zusätzlich durch einen Benzoring anneliiert sein kann. Beispielsweise steht Heterocyclyl für Piperidinyl, Pyrrolidinyl, Tetrahydrofuranyl, Dihydrofuranyl und Oxetanyl, Heteroaryl bedeutet einen aromatischen cyclischen Rest, der 3 bis 6 Ringatome enthält, von denen 1 bis 4 aus der Gruppe bestehend aus Sauerstoff, Stickstoff und Schwefel stammen, und der zusätzlich durch einen Benzoring annelliert sein kann. Beispielsweise steht Heteroaryl für Benzimidazol-2-yl, Furanyl, Imidazolyl, Isoxazolyl, Isothiazolyl, Oxazolyl, Pyrazinyl, Pyrimidinyl, Pyridazinyl, Pyridinyl, Benzisoxazolyl, Thiazolyl, Pyrrolyl, Pyrazolyl, Thiophenyl, 1 ,2,3-Oxadiazolyl, 1 ,2,4-Oxadiazolyl, 1 ,2,5- Oxadiazolyl, 1 ,3,4-Oxadiazolyl, 1 ,2,4-Triazolyl, 1 ,2,3-Triazolyl, 1 ,2,5-Triazolyl, 1 ,3,4- Triazolyl, 1 ,2,4-Triazolyl, 1 ,2,4-Thiadiazolyl, 1 ,3,4-Thiadiazolyl, 1 ,2,3-Thiadiazolyl, 1 ,2,5-Thiadiazolyl, 2H-1 ,2,3,4-Tetrazolyl, 1 H-1 ,2,3,4-Tetrazolyl, 1 ,2,3,4-Oxatriazolyl, 1 ,2,3,5-Oxatriazolyl, 1 ,2,3,4-Thiatriazolyl und 1 ,2,3,5-Thiatriazolyl. Heterocyclyl means a saturated, partially saturated or fully unsaturated cyclic radical containing from 3 to 6 ring atoms of which from 1 to 4 are selected from the group consisting of oxygen, nitrogen and sulfur, and which may additionally be annelated by a benzo ring. For example, heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl, Heteroaryl means an aromatic cyclic radical containing from 3 to 6 ring atoms of which from 1 to 4 are selected from the group consisting of oxygen, nitrogen and sulfur, and which may additionally be fused by a benzo ring. For example, heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl, 1, 2,3-oxadiazolyl, 1, 2 4-oxadiazolyl, 1, 2,5-oxadiazolyl, 1, 3,4-oxadiazolyl, 1, 2,4-triazolyl, 1, 2,3-triazolyl, 1, 2,5-triazolyl, 1, 3,4- Triazolyl, 1, 2,4-triazolyl, 1, 2,4-thiadiazolyl, 1, 3,4-thiadiazolyl, 1, 2,3-thiadiazolyl, 1, 2,5-thiadiazolyl, 2H-1,2,3, 4-tetrazolyl, 1 H-1, 2,3,4-tetrazolyl, 1, 2,3,4-oxatriazolyl, 1, 2,3,5-oxatriazolyl, 1, 2,3,4-thiatriazolyl and 1, 2 , 3,5-thiatriazolyl.
Ist eine Gruppe mehrfach durch Reste substituiert, so ist darunter zu verstehen, daß diese Gruppe durch ein oder mehrere gleiche oder verschiedene der genannten Reste substituiert ist. Analoges gilt für den Aufbau von Ringsystemen durch verschiedene Atome und Elemente. Dabei sollen solche Verbindungen vom Anspruchsbegehren ausgenommen sein, von denen der Fachmann weiß, dass sie unter If a group is repeatedly substituted by radicals, it is to be understood that this group is substituted by one or more identical or different radicals. The same applies to the construction of ring systems by different atoms and elements. In this case, such compounds should be excluded from the claim, which is known to the skilled person that under
Normalbedingungen chemisch instabil sind. Normal conditions are chemically unstable.
Die Verbindungen der allgemeinen Formel (I) können je nach Art und Verknüpfung der Substituenten als Stereoisomere vorliegen. Sind beispielsweise ein oder mehrere asymmetrisch substituierte Kohlenstoffatome vorhanden, so können Enantiomere und Diastereomere auftreten. Ebenso treten Stereoisomere auf, wenn Sulfoxide vorliegen. Stereoisomere lassen sich aus den bei der Herstellung anfallenden Gemischen nach üblichen Trennmethoden, beispielsweise durch chromatographische Trennverfahren, erhalten. Ebenso können Stereoisomere durch Einsatz stereoselektiver Reaktionen unter Verwendung optisch aktiver Ausgangs- und/oder Hilfsstoffe selektiv hergestellt werden. Die Erfindung betrifft auch alle Stereoisomeren und deren Gemische, die von der allgemeinen Formel (I) umfasst, jedoch nicht spezifisch definiert sind. Die Verbindungen der Formel (I) können Salze bilden. Salzbildung kann durch Depending on the nature and linkage of the substituents, the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetrically substituted carbon atoms are present, enantiomers and diastereomers may occur. Likewise, stereoisomers occur when sulfoxides are present. Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants. The invention also relates to all stereoisomers and mixtures thereof which are of the general formula (I), but not specifically defined. The compounds of formula (I) can form salts. Salt formation can through
Einwirkung einer Base auf Verbindungen der Formel (I) erfolgen. Geeignete Basen sind beispielsweise organische Amine, wie Trialkylamine, Morpholin, Piperidin und Pyridin sowie Ammonium-, Alkali- oder Erdalkalimetallhydroxide, -carbonate  Effect of a base on compounds of formula (I) take place. Examples of suitable bases are organic amines, such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates
und -hydrogencarbonate, insbesondere Natrium- und Kaliumhydroxid, Natrium- und Kaliumcarbonat und Natrium- und Kaliumhydrogencarbonat. Diese Salze sind and bicarbonates, in particular sodium and potassium hydroxide, sodium and Potassium carbonate and sodium and potassium bicarbonate. These salts are
Verbindungen, in denen der acide Wasserstoff durch ein für die Landwirtschaft geeignetes Kation ersetzt wird, beispielsweise Metallsalze, insbesondere Alkalimetallsalze oder Erdalkalimetallsalze, insbesondere Natrium- und Kaliumsalze, oder auch Ammoniumsalze, Salze mit organischen Aminen oder quartäre Ammoniumsalze, zum Beispiel mit Kationen der Formel [NRaRbRcRd]+, worin Ra bis Rd jeweils unabhängig voneinander einen organischen Rest, insbesondere Alkyl, Aryl, Aralkyl oder Alkylaryl darstellen. Infrage kommen auch Alkylsulfonium- und Alkylsulfoxoniumsalze, wie (Ci- C4)-Trialkylsulfonium- und (Ci-C4)-Trialkylsulfoxoniumsalze. Compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula NR a R b R c R d ] + , wherein R a to R d each independently represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl. Also suitable are alkylsulfonium and alkylsulfoxonium salts, such as (C 1 -C 4) -trialkylsulfonium and (C 1 -C 4) -trialkylsulfoxonium salts.
Die Verbindungen der 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. The compounds of 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. 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 a basic group, e.g. Amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
Bevorzugt sind Verbindungen der allgemeinen Formel (I) oder deren Salze, in denen die Brücke L für die Reste A1 bis A378 steht, wobei die gestrichelten Bindungen diejenigen Bindungen darstellen, welche die Brücke L an den Benzoylrest anbinden. Hierbei stellt die obere gestrichelte Linie die Bindung an das C-Atom 3 der allgemeinen Formel (I) und die untere gestrichelte Linie die Bindung an das C-Atom 4 der allgemeinen Formel (I) dar: Preference is given to compounds of the general formula (I) or salts thereof in which the bridge L is the radicals A1 to A378, where the dashed bonds represent those bonds which link the bridge L to the benzoyl radical. Here, the upper dashed line represents the bond to the C atom 3 of the general formula (I) and the lower dashed line represents the bond to the C atom 4 of the general formula (I):
(AD (A2) (A3) (A4) (A5) (A6) (AD (A2) (A3) (A4) (A5) (A6)
(A7) (A8) (A9) (A11) (A12) (A7) (A8) (A9) (A11) (A12)
(A13) (A14) (A15) (A16) (A17) (A18) (A13) (A14) (A15) (A16) (A17) (A18)
(A19) (A20) (A21) (A22) (A23) (A24) (A19) (A20) (A21) (A22) (A23) (A24)
(A25) (A26) (A27) (A28) (A29) (A25) (A26) (A27) (A28) (A29)
(A31 ) (A32) (A33) (A34) (A35) (A36) (A31) (A32) (A33) (A34) (A35) (A36)
(A37) (A38) (A39) (A40) (A41 ) (A42) (A37) (A38) (A39) (A40) (A41) (A42)
(A43) (A44) (A45) (A46) (A47) (A48) (A43) (A44) (A45) (A46) (A47) (A48)
(A49) (A50) (A51) (A52) (A53) (A54) (A49) (A50) (A51) (A52) (A53) (A54)
(A61) (A62) (A63) (A64) (A65) (A66) (A68) (A69) (A70) (A71) (A72) (A73) (A61) (A62) (A63) (A64) (A65) (A66) (A68) (A69) (A70) (A71) (A72) (A73)
(A81) (A82) (A84) (A85) (A86) (A87) (A81) (A82) (A84) (A85) (A86) (A87)
(A94) (A95) (A96) (A97) (A98) (A94) (A95) (A96) (A97) (A98)
(A100) (A101) (A102) (A103) (A104) (A105) (A100) (A101) (A102) (A103) (A104) (A105)
(A106) (A107) (A108) (A109) (A110) (A111 ) (A112) (A106) (A107) (A108) (A109) (A110) (A111) (A112)
(A114) (A115) (A116) (A117) (A118) (A119) (A114) (A115) (A116) (A117) (A118) (A119)
(A121) (A122) (A123) (A124) (A125) (A126) (A121) (A122) (A123) (A124) (A125) (A126)
(A127) (A129) (A132)  (A127) (A129) (A132)
(A151) (A152) (A153) (A154) (A155) (A156) (A157) (A151) (A152) (A153) (A154) (A155) (A156) (A157)
A158) (A159) (A160) (A161) (A162) (A163) A158) (A159) (A160) (A161) (A162) (A163)
(A164) (A165) (A166) (A167) (A164) (A165) (A166) (A167)
(A168) (A169) (A170) (A171) (A172) (A168) (A169) (A170) (A171) (A172)
(A178) (A179) (A181) (A182) (A178) (A179) (A181) (A182)
(A184) (A185) (A186) (A187) (A184) (A185) (A186) (A187)
(A188) (A189) (A190) (A191) (A192) (A188) (A189) (A190) (A191) (A192)
(A193) (A194) (A195) (A196) (A193) (A194) (A195) (A196)
(A215) (A216) (A217) (A218) (A219) (A220) (A215) (A216) (A217) (A218) (A219) (A220)
A221 ) (A222) (A223) (A224) (A225) (A226) A221) (A222) (A223) (A224) (A225) (A226)
(A233) (A234) (A235) (A236) (A238) (A233) (A234) (A235) (A236) (A238)
(A239) (A240) (A241 ) (A242) (A243) (A244) (A239) (A240) (A241) (A242) (A243) (A244)
A245) (A246) (A247) (A249) (A250) A245) (A246) (A247) (A249) (A250)
(A251 ) (A252) (A253) (A254) (A255) (A256) (A251) (A252) (A253) (A254) (A255) (A256)
(A257) (A258) (A259) (A260) (A261 ) (A262) (A257) (A258) (A259) (A260) (A261) (A262)
(A263) (A264) (A265) (A266) (A267) (A268) (A263) (A264) (A265) (A266) (A267) (A268)
(A269) (A270) (A271 ) (A272) (A273) (A269) (A270) (A271) (A272) (A273)
(A274) (A275) (A277) (A278) (A279) (A274) (A275) (A277) (A278) (A279)
(A280) (A281 ) (A282) (A283) (A284) (A285) (A280) (A281) (A282) (A283) (A284) (A285)
(A286) (A287) (A289) (A290) (A291 ) (A286) (A287) (A289) (A290) (A291)
(A304) (A305) (A306) (A307) (A308) (A309) (A304) (A305) (A306) (A307) (A308) (A309)
(A310) (A311 ) (A312) (A310) (A311) (A312)
(A320) (A321 ) (A322) (A323) (A324) (A325) (A326) (A320) (A321) (A322) (A323) (A324) (A325) (A326)
(A334) (A335) (A336) (A337) (A338) (A339) (A340) (A334) (A335) (A336) (A337) (A338) (A339) (A340)
(A34 (A342) (A343) (A344) (A345) (A346) (A347) (A34 (A342) (A343) (A344) (A345) (A346) (A347)
(A348) (A349) (A350) (A351 ) (A348) (A349) (A350) (A351)
(A354) (A355) (A356) (A357)  (A354) (A355) (A356) (A357)
(Α362) (Α367) (Α368) (Α362) (Α367) (Α368)
(A369) A370) (A371 ) (Α372) (Α373) (Α374) (A369) A370) (A371) (Α372) (Α373) (Α374)
(A375) (A376) (A377) (Α378) R7, R8, R12, R13, R22 und R23 bedeuten unabhängig voneinander jeweils (A375) (A376) (A377) (Α378) R 7 , R 8 , R 12 , R 13 , R 22 and R 23 are each independently
Wasserstoff, Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen- (C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen- (C3-C6)-cycloalkyl, (C3-C6)-Cycloalkenyl, Halogen-(C3-C6)-cycloalkenyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, (C3-C6)- Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkenyl-(Ci-C6)-alkyl, R1(0)C, R1(R1ON=)C, R10(0)C, (R1)2N(0)C, R1(R10)N(0)C, (R1)2N(R1)N(0)C, Hydrogen, halogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 - C 6 ) alkynyl, halogeno (C 3 -C 6 ) alkynyl, (C 3 -C 6 ) cycloalkyl, halogeno (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkenyl, halo (C 3 -C 6) cycloalkenyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, halo (C 3 -C 6) -cycloalkyl- (Ci-C 6) - alkyl, (C 3 -C 6) - cycloalkenyl, (Ci-C 6) alkyl, halo (C 3 -C 6) cycloalkenyl (Ci-C 6) alkyl, R 1 (0) C, R 1 (R 1 ON =) C, R 1 0 (0) C (R 1) 2 N (0) C, R 1 (R 1 0) N (0) C (R 1) 2 N (R 1 ) N (0) C
R1(0)C(R1)N(0)C, R20(0)C(R1)N(0)C, (R1)2N(0)C(R1)N(0)C, R2(0)2S(R1)N(0)C, R10(0)2S(R1)N(0)C, (R1)2N(0)2S(R1)N(0)C, R20, R1(0)CO, R2(0)2SO, R20(0)CO, (R1)2N(0)CO, (R1)2N, R1(0)C(R1)N, R2(0)2S(R1)N, R20(0)C(R1)N, (R1)2N(0)C(R1)N, R10(0)2S(R1)N, (R1)2N(0)2S(R1)N, R2(0)nS, R10(0)2S, (R1)2N(0)2S, R 1 (0) C (R 1 ) N (0) C, R 2 0 (0) C (R 1 ) N (O) C, (R 1 ) 2 N (O) C (R 1 ) N (0 ) C, R 2 (O) 2 S (R 1 ) N (O) C, R 1 O (O) 2 S (R 1 ) N (O) C, (R 1 ) 2 N (O) 2 S ( R 1 ) N (O) C, R 2 O, R 1 (O) CO, R 2 (O) 2 SO, R 2 O (0) CO, (R 1 ) 2 N (O) CO, (R 1 ) 2 N, R 1 (O) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N, R 2 O (0) C (R 1 ) N, (R 1 ) 2 N (0 ) C (R 1) N, R 1 0 (0) 2 S (R 1) N, (R 1) 2 N (0) 2 S (R 1) N, R 2 (0) n S, R 1 0 (0) 2 S, (R 1 ) 2 N (0) 2 S,
R1(0)C(R1)N(0)2S, R20(0)C(R1)N(0)2S, (R1)2N(0)C(R1)N(0)2S, R1(0)C-(Ci-C6)-Alkyl, R10(0)C-(Ci-C6)-Alkyl, (R1)2N(0)C-(Ci-C6)-Alkyl, (R10)(R1)N(0)C-(Ci-C6)-Alkyl, (R1)2N(R1)N(0)C-(Ci-C6)-Alkyl, R1(0)C(R1)N(0)C-(Ci-C6)-Alkyl, R20(0)C(R1)N(0)C- (Ci-C6)-Alkyl, (R1)2N(0)C(R1)N(0)C-(Ci-C6)-Alkyl, R2(0)2S(R1)N(0)C-(Ci-C6)-Alkyl, R10(0)2S(R1)N(0)C-(Ci-C6)-Alkyl, (R1)2N(0)2S(R1)N(0)C-(Ci-C6)-Alkyl, NC-(Ci-C6)- Alkyl, R10-(Ci-C6)-Alkyl, R1(0)CO-(Ci-C6)-Alkyl, R2(0)2SO-(Ci-C6)-Alkyl, R20(0)CO- (Ci-C6)-Alkyl, (R1)2N(0)CO-(Ci-C6)-Alkyl, (R1)2N-(Ci-C6)-Alkyl, R1(0)C(R1)N-(Ci-C6)- Alkyl, R2(0)2S(R1)N-(Ci-C6)-Alkyl, R20(0)C(R1)N-(Ci-C6)-Alkyl, (R1)2N(0)C(R1)N-(Ci- C6)-Alkyl, R10(0)2S(R1)N-(Ci-C6)-Alkyl, (R1)2N(0)2S(R1)N-(Ci-C6)-Alkyl, R2(0)nS-(Ci- C6)-Alkyl, R10(0)2S-(Ci-C6)-Alkyl, (R1)2N(0)2S-(Ci-C6)-Alkyl, R1(0)C(R1)N(0)2S-(Ci- C6)-Alkyl, R20(0)C(R1)N(0)2S-(Ci-C6)-Alkyl, (R1)2N(0)C(R1)N(0)2S-(Ci-C6)-Alkyl, (R50)2(0)P-(Ci-C6)-Alkyl, Phenyl, Heteroaryl, Heterocyclyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, wobei die sechs letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, Cyano, Rhodano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, R10(0)C, R 1 (O) C (R 1 ) N (O) 2 S, R 2 O (0) C (R 1 ) N (O) 2 S, (R 1 ) 2 N (O) C (R 1 ) N (0) 2 S, R 1 (O) C- (C 1 -C 6 ) -alkyl, R 1 0 (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) C- (C 1 -C 6 ) -alkyl, (R 10) (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (R 1 ) N (O) C- ( C 1 -C 6 ) -alkyl, R 1 (O) C (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, R 2 O (0) C (R 1 ) N (O) C- (Ci-C 6) alkyl, (R 1) 2 N (0) C (R 1) N (0) C- (Ci-C 6) alkyl, R 2 (0) 2 S (R 1) N (0) C- (Ci-C 6) alkyl, R 1 0 (0) 2 S (R 1) N (0) C- (Ci-C 6) -alkyl, (R 1) 2 N (0) 2 S (R 1) N (0) C- (Ci-C 6) -alkyl, NC (Ci-C 6) - alkyl, R 1 0- (Ci-C 6) alkyl, R 1 (0) CO (C 1 -C 6 ) -alkyl, R 2 (O) 2 SO- (C 1 -C 6 ) -alkyl, R 2 0 (0) CO- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (0) CO- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N- (C 1 -C 6 ) -alkyl, R 1 (O) C (R 1 ) N- (C 1 -C 6 ) - Alkyl, R 2 (O) 2 S (R 1 ) N - (C 1 -C 6 ) -alkyl, R 2 0 (O) C (R 1 ) N - (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (0) C (R 1 ) N- (C 1 -C 6 ) -alkyl, R 1 0 (0) 2 S (R 1 ) N- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (0) 2 S (R 1 ) N- (C 1 -C 6 ) -alkyl, R 2 (O) n S- (C 1 -C 6 ) -alkyl, R 1 0 (0) 2 S- (Ci-C 6 ) -alkyl, (R 1 ) 2 N (O) 2 S- (C 1 -C 6 ) -alkyl, R 1 (0 ) C (R 1 ) N (O) 2 S- (C 1 -C 6 ) -alkyl, R 2 0 (0) C (R 1 ) N (O) 2 S- (C 1 -C 6 ) -alkyl, ( R 1 ) 2 N (O) C (R 1 ) N (O) 2 S- (C 1 -C 6 ) -alkyl, (R 5 0) 2 (O) P- (C 1 -C 6 ) -alkyl, phenyl , Heteroaryl, heterocyclyl, phenyl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, where the six last-mentioned radicals are each represented by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, R 1 0 (0) C,
(R1)2N(0)C, R10, (R1)2N, R2(0)nS, R10(0)2S, (R1)2N(0)2S und R10-(Ci-C6)-Alkyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R9, R10, R14, R15, R16, R17, R20, R21, R24 und R25 bedeuten unabhängig voneinander jeweils Wasserstoff, Halogen, (Ci-C-4)-Alkyl, (Ci-C4)-Halogenalkyl, (Ci-C )-Alkoxy, (Ci- C4)-Halogenalkoxy oder (Ci-C4)-Alkoxy-(Ci-C4)-alkyl oder je zwei geminale R9, R10, R14, R15, R16, R1 7, R20, R21 , R24 und R25 bilden gemeinsam mit dem Kohlenstoffatom, an das sie gebunden sind, eine Carbonylgruppe oder ein(R 1 ) 2 N (O) C, R 1 O, (R 1 ) 2 N, R 2 (O) n S, R 1 O (0) 2 S, (R 1 ) 2 N (O) 2 S and R 1 is 0- (C 1 -C 6 ) -alkyl, and wherein heterocyclyl carries n oxo groups, R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 are each independently hydrogen, halogen, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (Ci-C) alkoxy, (Ci C 4) -haloalkoxy or (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkyl or in each case two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 together with the carbon atom to which they are attached form a carbonyl group or
Oxim der Formel C=NOR1 oder Oxime of the formula C = NOR 1 or
je zwei geminale R9, R10, R14, R15, R16, R17, R20, R21 , R24 und R25 bedeuten ein Acetal der Formel -O-(C2-C4)-Alkylen-O-, two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 is an acetal of the formula -O- (C 2 -C 4 ) -alkylene O-,
R1 1 , R18, R19, R26 und R27 bedeuten unabhängig voneinander jeweils Wasserstoff, (Ci- C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)- Alkinyl, Halogen-(C3-C6)-alkinyl, wobei die sechs vorstehend genannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Cyano, R2(0)nS, (R1 )2N , R10, R1(0)C, R10(0)C, R1(0)CO, R20(0)CO, R1(0)C(R1 )N, R2(0)2S(R1 )N, (C3-C6)- Cycloalkyl, Heteroaryi, Heterocyclyi und Phenyi substituiert sind, wobei die vier letztgenannten Reste durch s Reste aus der Gruppe bestehend aus (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-Ce)-alkoxy und Halogen substituiert sind, und wobei Heterocyclyi n Oxogruppen trägt, oder R1 1 , R18, R19, R26 und R27 bedeuten unabhängig voneinander jeweils (C3-C7)- Cycloalkyl, Heteroaryi, Heterocyclyi oder Phenyi, wobei die vier vorstehend genannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (Ci-C6)-Alkyl- S(0),„ (Ci-C6)- Alkoxy, Halogen-(Ci-Ce)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C4)-alkyl substituiert sind, und wobei Heterocyclyi n Oxogruppen trägt, R 1 1, R 18, R 19, R 26 and R 27 are each independently hydrogen, (Ci- C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl , Halo (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, halo (C 3 -C 6 ) -alkynyl, where the six radicals mentioned above are each represented by s radicals from the group consisting of nitro, cyano , R 2 (0) n S, (R 1 ) 2 N , R 1 O, R 1 (0) C, R 1 0 (0) C, R 1 (0) CO, R 2 0 (0) CO, R 1 (0) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N, (C 3 -C 6 ) -cycloalkyl, heteroaryl, heterocyclyl and phenyl, wherein the four last-mentioned radicals are substituted by s radicals from the group consisting of (C 1 -C 6) -alkyl, halogeno (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxy, halogeno (C 1 -C 6) -alkoxy and halogen, and wherein heterocyclynisubstituted oxo groups R 1 1 , R 18 , R 19 , R 26 and R 27 independently of one another are each (C 3 -C 7) -cycloalkyl, heteroaryl, heterocyclyl or phenyl, wherein the four radicals mentioned above each consist of s radicals from the group from halogen , Nitro, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C6) alkyl- S (0), " (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -alkyl, and where heterocyclyl carries oxo groups,
R28, R29, R30 und R31 bedeuten unabhängig voneinander jeweils Wasserstoff, Nitro, Halogen, Cyano, Rhodano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl,R 28, R 29, R 30 and R 31 are each independently hydrogen, nitro, halogen, cyano, thiocyanato, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6 ) alkenyl,
Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkenyl, Halogen-(C3-C6)-cycloalkenyl, (C3- C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, (C3-C6)- Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkenyl-(Ci-C6)-alkyl, R1(O)C, R1(R1ON=)C, RO(O)C, (R1 )2N(O)C, R1(R1O)N(O)C, (R1 )2N(R1 )N(O)C, Halogeno (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, halogeno (C 3 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, halogeno (C 3 -) C6) cycloalkyl, (C3-C6) cycloalkenyl, halo (C 3 -C 6) cycloalkenyl, (C 3 - C 6) -cycloalkyl- (Ci-C (6) alkyl, halo C 3 - C6) cycloalkyl- (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkenyl, (Ci-C 6) alkyl, halo (C 3 -C 6) cycloalkenyl (C 6 ) -alkyl, R 1 (O) C, R 1 (R 1 ON =) C, RO (O) C, (R 1 ) 2 N (O) C, R 1 (R 1 O) N (O) C , (R 1 ) 2 N (R 1 ) N (O) C,
R1(O)C(R1 )N(O)C, R2O(O)C(R1 )N(O)C, (R1 )2N(O)C(R1 )N(O)C, R2(O)2S(R1 )N(O)C, R1O(O)2S(R1 )N(O)C, (R1 )2N(O)2S(R1 )N(O)C, R2O, R1(O)CO, R2(O)2SO, R2O(O)CO, (R1 )2N(O)CO, (R1 )2N, R1(O)C(R1 )N, R2(O)2S(R1 )N, R2O(O)C(R1 )N, (R1 )2N(O)C(R1 )N, R1O(O)2S(R1 )N, (R1 )2N(O)2S(R1 )N, R2(O)nS, R1O(O)2S, (R1 )2N(O)2S, R1(O)C(R1 )N(O)2S, R2O(O)C(R1 )N(O)2S, (R1 )2N(O)C(R1 )N(O)2S, (R5O)2(O)P, R1(O)C- (Ci-C6)-Alky!, RO(O)C-(Ci-C6)-Alkyl, (R1)2N(O)C-(Ci-C6)-Alkyl, (R1O)(R1 )N(O)C-(Ci- C6)-Alkyl, (R1 )2N(R1 )N(O)C-(Ci-C6)-Alkyl, R1(O)C(R1)N(O)C-(Ci-C6)-Alkyl, R 1 (O) C (R 1 ) N (O) C, R 2 O (O) C (R 1 ) N (O) C, (R 1 ) 2 N (O) C (R 1 ) N (O ) C, R 2 (O) 2 S (R 1 ) N (O) C, R 1 O (O) 2 S (R 1 ) N (O) C, (R 1 ) 2 N (O) 2 S ( R 1 ) N (O) C, R 2 O, R 1 (O) CO, R 2 (O) 2 SO, R 2 O (O) CO, (R 1 ) 2 N (O) CO, (R 1 ) 2 N, R 1 (O) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N, R 2 O (O) C (R 1 ) N, (R 1 ) 2 N (O ) C (R 1 ) N, R 1 O (O) 2 S (R 1 ) N, (R 1 ) 2 N (O) 2 S (R 1 ) N, R 2 (O) n S, R 1 O (O) 2 S, (R 1 ) 2 N (O) 2 S, R 1 (O) C (R 1 ) N (O) 2 S, R 2 O (O) C (R 1 ) N (O) 2 S, (R 1 ) 2 N (O) C (R 1 ) N (O) 2 S, (R 5 O) 2 (O) P, R 1 (O) C- (C 1 -C 6 ) -alkyl, RO (O) C- (C 1 -C 6 ) -alkyl, ( R 1 ) 2 N (O) C- (C 1 -C 6 ) -alkyl, (R 1 O) (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N ( R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, R 1 (O) C (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl,
R2O(O)C(R1 )N(O)C-(Ci-C6)-AlkyS, (R1 )2N(O)C(R1 )N(O)C-(Ci-C6)-Alkyl, R 2 O (O) C (R 1 ) N (O) C- (C 1 -C 6 ) -AlkyS, (R 1 ) 2 N (O) C (R 1 ) N (O) C- (Ci-C 6 ) -alkyl,
R2(O)2S(R1 )N(O)C-(Ci-C6)-Alkyl, R1O(O)2S(R1 )N(O)C-(Ci-C6)-Alkyl, R 2 (O) 2 S (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, R 1 O (O) 2 S (R 1 ) N (O) C- (C 1 -C 6 ) alkyl,
(R1 )2N(O)2S(R1 )N(O)C-(Ci-C6)-Alkyl, NC-(Ci-C6)-Alky!, R1O-(Ci-C6)-Alkyl, R1(O)CO- (Ci-C6)-Alkyl, R2(O)2SO-(Ci-C6)-AlkyS, R2O(O)CO-(Ci-C6)-Alkyl, (R1)2N(O)CO-(Ci-C6)- AlkyS, (R1 )2N-(Ci-C6)-Alkyl, R1(O)C(R1)N-(Ci-C6)-Alkyl, R2(O)2S(R1 )N-(Ci-C6)-Alkyl, R2O(O)C(R1)N-(Ci-C6)-Alkyl, (R1)2N(O)C(R1)N-(C1-C6)-Alkyl, R1O(O)2S(R1 )N-(Ci-C6)- Alkyi, (R1)2N(O)2S(R1)N-(Ci-C6)-Alkyl, R2(O)nS-(Ci-C6)-Alky!, R1O(O)2S-(C1-C6)-Alkyl! (R1)2N(O)2S-(C1-C6)-Alkyl, R1(O)C(R1 )N(O)2S-(Ci-C6)-Alkyl, R2O(O)C(R1 )N(O)2S-(Ci- C6)-Alkyl, (R1 )2N(O)C(R1 )N(O)2S-(Ci-C6)-Alkyl, (R5O)2(O)P-(Ci-C6)-ASkyl, Phenyl, Heteroaryl, Heterocyclyl, Phenyl-(Ci-C-6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl- (Ci-C6)-alkyl, wobei die sechs letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, Cyano, Rhodano, (Ci-Ce)-Alkyl, Halogen-(Ci- C6)-alkyl, (C3-C6)-Cycloalkyl, R1O(O)C, (R1)2N(O)C, R1O, (R1)2N, R2(O)nS, R1O(O)2S, (R1 )2N(O)2S und R1O-(Ci-C6)-Alkyl substituiert sind, und wobei Heterocyclyl n (R 1) 2 N (O) 2 S (R 1) N (O) C- (Ci-C6) alkyl, NC (Ci-C 6) -Alky !, R 1 O- (Ci-C 6 ) Alkyl, R 1 (O) CO- (C 1 -C 6 ) -alkyl, R 2 (O) 2 SO- (C 1 -C 6 ) -alkyl, R 2 O (O) CO- (C 1 -C 6 ) -Alkyl, (R 1 ) 2 N (O) CO- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N- (C 1 -C 6 ) -alkyl, R 1 (O) C (R 1 ) N- (Ci-C 6) alkyl, R 2 (O) 2 S (R 1) N- (Ci-C 6) alkyl, R 2 O (O) C (R 1) N- (Ci-C 6 ) -alkyl, (R 1 ) 2 N (O) C (R 1 ) N- (C 1 -C 6 ) -alkyl, R 1 O (O) 2 S (R 1 ) N- (C 1 -C 6 ) - Alkyi, (R 1 ) 2 N (O) 2 S (R 1 ) N - (C 1 -C 6 ) -alkyl, R 2 (O) nS- (C 1 -C 6 ) -alkyl, R 1 O ( O) 2 S- (C 1 -C 6 ) -alkyl ! (R 1) 2 N (O) 2 S- (C 1 -C 6) alkyl, R 1 (O) C (R 1) N (O) 2 S- (Ci-C 6) alkyl, R 2 O (O) C (R 1 ) N (O) 2 S- (C 1 -C 6 ) alkyl, (R 1 ) 2 N (O) C (R 1 ) N (O) 2 S- (C 1 -C 6 ) -Alkyl, (R 5 O) 2 (O) P- (C 1 -C 6 ) -alkyl, phenyl, heteroaryl, heterocyclyl, phenyl- (C 1 -C 6) -alkyl, heteroaryl- (C 1 -C 6) - alkyl, heterocyclyl (C 1 -C 6) -alkyl, where the six last-mentioned radicals are in each case represented by s radicals from the group consisting of nitro, halogen, cyano, rhodano, (C 1 -C 6 ) -alkyl, halogen (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, R 1 O (O) C, (R 1 ) 2 N (O) C, R 1 O, (R 1 ) 2 N, R 2 (O) n S , R 1 O (O) 2 S, (R 1 ) 2 N (O) 2 S and R 1 O- (C 1 -C 6 ) -alkyl, and wherein heterocyclyl n
Oxogruppen trägt, und wobei die Reste Q, R, X, W, R\ R2, R3, R4, R5, R6 und R' sowie die Variablen n und s die oben angegebenen Bedeutungen haben. Carries oxo groups, and wherein the radicals Q, R, X, W, R \ R 2 , R 3 , R 4 , R 5 , R 6 and R 'and the variables n and s have the meanings given above.
Besonders bevorzugt sind Verbindungen der allgemeinen Formel (I), worin Particular preference is given to compounds of the general formula (I) in which
Q bedeutet einen Rest Q1 , Q2, Q3 oder Q4, Q represents a remainder Q1, Q2, Q3 or Q4,
X bedeutet Nitro, Halogen, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)- Alkenyl, (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, R1(O)C, X is nitro, halo, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) - alkenyl, (C 2 -C 6) -alkynyl, (C 3 -C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, halo (C 3 -C 6) cycloalkyl (C 1 -C 6 ) -alkyl, R 1 (O) C,
R1(R1ON=)C, R1O(O)C, (R1)2N(O)C, RO, (R1)2N, R1(O)C(R1)N, R2(O)2S(R1)N, R 1 (R 1 ON =) C, R 1 O (O) C, (R 1 ) 2 N (O) C, RO, (R 1 ) 2 N, R 1 (O) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N,
R2O(O)C(R1)N, (R1)2N(O)C(R1)N, R2(O)„S, R1O(O)2S, (R1)2N(O)2S, (R5O)2(O)P, R1(O)C-(Ci-C6)-Alkyl, R1O(O)C-(Ci-C6)-Alkyl, (R1)2N(O)C-(C1-C6)-Alkyl, NC-(Ci-Ce)- Alkyl, RO-(Ci-C6)-Alkyl, (R1)2N-(Ci-C6)-Alkyl, R1(O)C(R1)N-(Ci-C6)-Alkyl, R 2 O (O) C (R 1 ) N, (R 1 ) 2 N (O) C (R 1 ) N, R 2 (O) "S, R 1 O (O) 2 S, (R 1 ) 2 N (O) 2 S, (R 5 O) 2 (O) P, R 1 (O) C- (C 1 -C 6 ) -alkyl, R 1 O (O) C- (C 1 -C 6 ) - Alkyl, (R 1 ) 2 N (O) C- (C 1 -C 6 ) -alkyl, NC- (C 1 -C 6 ) -alkyl, RO- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (C 1 -C 6 ) -alkyl, R 1 (O) C (R 1 ) N- (C 1 -C 6 ) -alkyl,
R2(O)2S(R1)N-(Ci-C6)-Alkyl, R2O(O)C(R1)N-(Ci-C6)-Alkyl, (R1)2N(O)C(R1)N-(Ci-C6)- Alkyl, R2(0)nS-(Ci-C6)-Alkyl, R10(0)2S-(Ci-C6)-Alkyl, (R1)2N(0)2S-(Ci-C6)-Alkyl! (R50)2(0)P-(Ci-C6)-Alkyl, Phenyl, Heteroaryl, Heterocyclyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-Ce>)-alkyl, wobei die sechs letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, Cyano, Rhodano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, R10, (R1)2N, R2(0)nS, R10(0)2S, (R1)2N(0)2S und R10-(Ci-C6)-Alkyl substituiert sind und wobei Heterocyclyl n R 2 (O) 2 S (R 1 ) N- (C 1 -C 6 ) -alkyl, R 2 O (O) C (R 1 ) N- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) C (R 1 ) N- (C 1 -C 6 ) - Alkyl, R 2 (O) nS- (C 1 -C 6 ) -alkyl, R 1 0 (O) 2 S- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) 2S- (C 1 -C 4) -alkyl C 6 ) -alkyl ! (R 5 O) 2 (O) P- (C 1 -C 6 ) -alkyl, phenyl, heteroaryl, heterocyclyl, phenyl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- ( Ci-Ce > ) -alkyl, wherein the six last mentioned radicals in each case by s radicals from the group consisting of nitro, halogen, cyano, Rhodano, (Ci-C 6 ) alkyl, halogeno (Ci-C 6 ) alkyl, R 1 0, (R 1 ) 2 N, R 2 (O) n S, R 1 0 (0) 2 S, (R 1 ) 2 N (O) 2 S and R 1 0- (C 1 -C 6 ) Alkyl are substituted and wherein heterocyclyl n
Oxogruppen trägt, Wearing oxo groups,
W bedeutet Wasserstoff, Halogen, Nitro, Cyano, (Ci-CeJ-Alkyl, Halogen-(Ci-Ce)- alkyl, (C3-C )-Cycloalkyl, (Ci-C6)-Alkoxy, (Ci-C6)-Alkyl-(0)nS-, R10(0)C, (R1)2N, R1(0)C(R1)N oder R2(0)2S(R1)N, W is hydrogen, halogen, nitro, cyano, (Ci-CeJ-alkyl, halogeno (Ci-Ce) - alkyl, (C 3 -C) -cycloalkyl, (Ci-C 6 ) -alkoxy, (Ci-C 6 ) -Alkyl- (O) n S-, R 1 O (0) C, (R 1 ) 2 N, R 1 (O) C (R 1 ) N or R 2 (O) 2 S (R 1 ) N .
R bedeutet Wasserstoff, Rx bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2- C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, wobei die sechs vorstehend genannten Reste jeweils durch s Reste aus der Gruppe bestehend aus R2(0)nS, (R1)2N, R10, R1(0)C, RO(0)C, R1(0)CO, R20(0)CO, R1(0)C(R1)N, R2(0)2S(R1)N, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocyclyl und Phenyl substituiert sind, wobei die vier letztgenannten Reste durch s Reste aus der Gruppe bestehend aus (Ci-CeJ-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-Ce)-Alkoxy und Halogen substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, oder Rx bedeutet (C3-C )-Cycloalkyl, wobei dieser Rest durch s Reste aus der Gruppe bestehend aus Halogen, (Ci-Ce)-Alkyl und Halogen-(Ci-Ce)-alkyl substituiert ist, R is hydrogen, R x represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 - C6) alkenyl, (C 2-C6) alkynyl, halo (C3-C6) -alkynyl, where the radicals mentioned above six respectively by s radicals selected from the group consisting (from R 2 0) n S, (R 1) 2 N, R 1 0 , R 1 (0) C, RO (0) C, R 1 (0) CO, R 2 0 (0) CO, R 1 (0) C (R 1) N, R 2 (0) 2 S (R 1 ) N, (C 3 -C 6) -cycloalkyl, heteroaryl, heterocyclyl and phenyl, where the four last-mentioned radicals are represented by s radicals from the group consisting of (C 1 -C 6 -alkyl, halogeno (C 1 -C 6) -alkyl, (Ci-Ce) alkoxy and halogen are substituted, and whereby Heterocyclyl carries n oxo groups, or R x means (C3-C) -cycloalkyl, whereby this remainder by s remainders from the group consisting of halogen, (Ci-Ce) - Alkyl and halo (C 1 -C 6) -alkyl,
RY bedeutet Wasserstoff, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C/)-Cycloalkyl, (Ci-C6)-Alkoxy, Methoxycarbonyl, Methoxycarbonylmethyl, Halogen, Amino, R Y is hydrogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C /) - cycloalkyl, (Ci-C6) alkoxy, methoxycarbonyl, methoxycarbonylmethyl, halogen, amino .
Aminocarbonyl oder Methoxymethyl, Aminocarbonyl or methoxymethyl,
Rz bedeutet Wasserstoff, (Ci-C6)-Alkyl, R1O-(Ci-C6)-Alkyl, R'CH2, (C3-C7)- Cycloalkyl, Halogen-(Ci-C6)-alkyl, R1O, R1(H)N, Methoxycarbonyl, Acetylamino oder Methylsulfonyl, R1 bedeutet Wasserstoff, (Ci-C6)-A!kyS, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cyc!oalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-0-(Ci-C6)- alkyl, Cycloalkyl-(Ci-C6)-a!kyl-0-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroary!, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, Phenyl-O-(Ci-Ce)- alkyl, Heteroaryl-0-(Ci-C6)-alkyl, Heterocyclyl-0-(Ci-C6)-alkyl, wobei die neun letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, R30(0)C, (R3)2N(0)C, R30, (R3)2N, R4(0)nS und R30-(d-C6)-Alkyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R z is hydrogen, (C 1 -C 6 ) -alkyl, R 1 O- (C 1 -C 6 ) -alkyl, R'CH 2 , (C 3 -C 7 ) -cycloalkyl, halogeno (C 1 -C 6 ) -alkyl, R 1 O, R 1 (H) N, methoxycarbonyl, acetylamino or methylsulfonyl, R 1 represents hydrogen, (Ci-C 6) -A! KyS, halo (Ci-C 6) alkyl, (C3-C 6) -Cyc! Oalkyl, halo (C3-C6) cycloalkyl, ( C 3 -C 6) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, cycloalkyl- (C 1 -C 6 ) -alkyl-0 (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6 ) -alkyl, Phenyl-O- (C 1 -C 6) -alkyl, heteroaryl-0- (C 1 -C 6) -alkyl, heterocyclyl-0- (C 1 -C 6) -alkyl, where the nine last-mentioned radicals are in each case represented by s radicals from the group consisting of Nitro, halogen, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, R 3 0 (0) C, (R 3 ) 2 N (O) C, R 3 0, (R 3 ) 2 N, R 4 (O) n S and R 3 are 0- (C 1 -C 6) -alkyl, and wherein heterocyclyl carries n oxo groups,
R2 bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, Halogen-(C3- C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-0-(Ci-C6)-alkyl, R 2 is (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) cycloalkyl, halo (C 3 - C 6) cycloalkyl, (C3-C6 ) -Cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl,
Cycloalkyl-(Ci-C6)-alkyl-0-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, Phenyl-O-(Ci-Ce)- alkyl, Heteroaryl-0-(Ci-C6)-alkyl, Heterocyclyl-0-(Ci-C6)-alkyl, wobei die neun letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, R30(0)C, (R3)2N(0)C, R30, (R3)2N, R4(0)nS und R30-(Ci-C6)-Alkyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Cycloalkyl- (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl, Heterocyclyl- (C 1 -C 6 ) -alkyl, phenyl-O- (C 1 -C 6 ) -alkyl, heteroaryl-0- (C 1 -C 6 ) -alkyl, heterocyclyl-0- (C 1 -C 6) -alkyl, where the nine the last-mentioned radicals in each case by s radicals from the group consisting of nitro, halogen, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, R 3 0 (O) C, (R 3 ) 2 N ( 0) C, R 3 0, (R 3 ) 2 N, R 4 (O) n S and R 3 are 0- (C 1 -C 6) -alkyl, and wherein heterocyclyl carries n oxo groups,
R3 bedeutet Wasserstoff oder (Ci-C6)-Alkyl, R4 bedeutet (Ci-C6)-Alkyl, R5 bedeutet Wasserstoff oder (d-C4)-Alkyl, R 3 is hydrogen or (C 1 -C 6 ) -alkyl, R 4 is (C 1 -C 6 ) -alkyl, R 5 is hydrogen or (C 1 -C 4 ) -alkyl,
R' bedeutet Acetoxy, Acetamido, Methoxycarbonyl oder (C-3-C6)-Cycloalkyl, n bedeutet 0, 1 oder 2, s bedeutet 0, 1 , 2 oder 3, R 'is acetoxy, acetamido, methoxycarbonyl or (C-3-C6) -cycloalkyl, n is 0, 1 or 2, s is 0, 1, 2 or 3,
L bedeutet eine Brücke ausgewählt aus der Gruppe bestehend aus A1 , A2, A3, A4, A5, A6, A7, A8, A9, A10, A1 1 , A12, A13, A14, A17, A25, A26, A27, A28, A29, A30, A31 , A32, A33, A34, A35, A36, A37, A38, A41 , Α49, Α50, Α51 , Α53, Α55, Α57, Α59, Α61 , Α62, Α72, Α139, Α140, Α141 , Α142, Α143, Α144, Α145, Α146, Α147, Α148, Α149, Α150, Α151 , Α157, Α 58, Α168, Α274, Α275, Α276, Α277, Α278, Α279, Α280, Α281 , Α282, Α283, Α284, Α285, Α286, Α287, Α363, Α364, Α365, Α366, Α367, Α368, Α369, Α370, Α371 , Α372 und Α373, L represents a bridge selected from the group consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A1, A12, A13, A14, A17, A25, A26, A27, A28, A29 , A30, A31, A32, A33, A34, A35, A36, A37, A38, A41, 49, 50, 51, 53, 55, 57, 59, 61, 62, 72, 13, 14, 14, 14, 14, 144, Α145, Α146, Α147, Α148, Α149, Α150, Α151, Α157, Α58, Α168, Α274, Α275, Α276, Α277, Α278, Α279, Α280, Α281, Α282, Α283, Α284, Α285, Α286, Α287, Α363 , Α364, Α365, Α366, Α367, Α368, Α369, Α370, Α371, Α372 and Α373,
R7, R8, R12, R13, R22 und R23 bedeuten unabhängig voneinander jeweils R 7 , R 8 , R 12 , R 13 , R 22 and R 23 are each independently
Wasserstoff, Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, R1(0)C, R1(R1ON=)C, R10(0)C, (R1)2N(0)C, R20, R1(0)CO, (R1)2N, R1(0)C(R1)N, R2(0)nS, R10-(Ci-C6)-Alkyl oder R2(0)nS-(Ci-C6)- Alkyl, Hydrogen, halogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, R 1 (0 ) C, R 1 (R 1 ON =) C, R 1 O (0) C, (R 1 ) 2 N (O) C, R 2 O, R 1 (O) CO, (R 1 ) 2 N, R 1 (0) C (R 1) N, R 2 (0) n S, R 1 0- (Ci-C 6) alkyl or R 2 (0) n S- (Ci-C 6) - alkyl,
R9, R10, R14, R15, R16, R17, R20, R21, R24 und R25 bedeuten unabhängig voneinander jeweils Wasserstoff, Halogen, (Ci-C4)-Alkyl, (Ci-C4)-Halogenalkyl oder (Ci-C4)-Alkoxy, oder je zwei geminaie R9, R10, R14, R15, R16, R17, R20, R21, R24 und R25 bilden gemeinsam mit dem Kohlenstoffatom, an das sie gebunden sind, eine Carbonylgruppe oder einR 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 are each independently hydrogen, halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) Haloalkyl or (C 1 -C 4) -alkoxy, or two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 form together with the carbon atom, to which they are attached, a carbonyl group or a
Oxim der Formel C=NOR1 oder je zwei geminaie R9, R10, R14, R15, R16, R17, R20, R21, R24 und R25 bedeuten ein Acetal der Formel -0-(C2-C4)-Alkylen-0-, Oxime of the formula C = NOR 1 or in each case two geminaie R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 is an acetal of the formula -0- (C 2 -C4) -alkylene-0-,
R11, R18, R19, R26 und R27 bedeuten unabhängig voneinander jeweils Wasserstoff oder (Ci-Cr -Alkyl, wobei die (Ci-Ce)-Alkylgruppe durch s Reste aus der Gruppe R 11 , R 18 , R 19 , R 26 and R 27 are each independently hydrogen or (Ci-Cr-alkyl, wherein the (Ci-Ce) alkyl group by s radicals from the group
bestehend aus R2(0)nS, (R1)2N, R10, R1(0)C, R10(0)C, R1(0)CO, R20(0)CO, R1(0)C(R1)N, R2(0)2S(R1)N, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocyclyl und Phenyi substituiert sind, wobei die vier letztgenannten Reste durch s Reste aus der Gruppe bestehend aus (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)- alkoxy und Halogen substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, oder R11, R18, R19, R26 und R27 bedeuten unabhängig voneinander jeweils (C3-C7)- Cycloalkyl, Heteroaryl, Heterocyclyl oder Phenyi, wobei die vier vorstehend genannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, (Ci-Ce)- Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (Ci-C6)-Alkyl- S(O)n, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C4)-alkyl substituiert sind, consisting of R 2 (0) n S, (R 1) 2 N, R 1 is 0, R 1 (0) C, R 1 0 (0) C, R 1 (0) CO, R 2 0 (0) CO , R 1 (O) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N, (C 3 -C 6 ) -cycloalkyl, heteroaryl, heterocyclyl and phenyl are substituted, the four latter radicals by s radicals from the group consisting of (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and halogen are substituted, and where heterocyclyl carries n oxo groups, or R 11 , R 18 , R 19 , R 26 and R 27 each independently denote (C 3 -C 7) -cycloalkyl, heteroaryl, heterocyclyl or phenyl, where the four radicals mentioned above are in each case represented by s radicals from the group consisting of halogen, nitro, (Ci-Ce) - Alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 6) -alkyl- S (O) n, (Ci-C 6) alkoxy, halo ( Ci-C6) -alkoxy and (Ci-C6) -alkoxy- (Ci-C4) -alkyl are substituted,
R28, R29, R30 und R31 bedeuten unabhängig voneinander jeweils Wasserstoff, Nitro, Halogen, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, Halogen-(C3- C6)-cycloalkyl, R1(O)C, R1(R1ON=)C, R1O(O)C, (R1 )2N(O)C, R2O, R1(O)CO, (R1 )2N, R1(O)C(R1 )N, R2(O)nS, R1O(O)2S, R1(O)C-(Ci-C6)-Alkyl, R1O(O)C-(Ci-C6)-Alkyl, (R1 )2N(O)C-(Ci-C6)-Alkyl, NC-(Ci-C6)-Alkyl, R1O-(Ci-C6)-Alkyl, R1(O)CO-(Ci-C6)-Alkyl, (R1 )2N-(Ci-C6)-Alkyl, R1(O)C(R1 )N-(Ci-C6)-Alkyl, R2(O)nS-(Ci-C6)-Alkyl, Phenyl, Heteroaryl, Heterocyclyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl- (Ci-CeJ-alkyl, wobei die sechs letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, R1O(O)C, (R1 )2N(O)C, RO, (R1 )2N, R2(O)nS, R1O(O)2S, R 28, R 29, R 30 and R 31 are each independently hydrogen, nitro, halogen, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) Cycloalkyl, halo (C 3 -C 6 ) cycloalkyl, R 1 (O) C, R 1 (R 1 ON =) C, R 1 O (O) C, (R 1 ) 2 N (O) C , R 2 O, R 1 (O) CO, (R 1 ) 2 N, R 1 (O) C (R 1 ) N, R 2 (O) n S, R 1 O (O) 2 S, R 1 (O) C- (C 1 -C 6 ) -alkyl, R 1 O (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) C- (C 1 -C 6 ) -alkyl , NC- (C 1 -C 6 ) -alkyl, R 1 O- (C 1 -C 6 ) -alkyl, R 1 (O) CO- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N- (Ci -C 6) alkyl, R 1 (O) C (R 1) N- (Ci-C 6) alkyl, R 2 (O) n S- (Ci-C 6) alkyl, phenyl, heteroaryl, heterocyclyl , Phenyl- (C 1 -C 6) -alkyl, heteroaryl- (C 1 -C 6) -alkyl, heterocyclyl- (C 1 -C 6 -alkyl, where the six last-mentioned radicals are in each case represented by s radicals from the group consisting of nitro, halogen, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, R 1 O (O) C, (R 1 ) 2 N (O) C, RO, ( R 1 ) 2 N, R 2 (O) n S, R 1 O (O) 2 S,
(R1 )2N(O)2S und R1O-(Ci-C6)-Alkyl substituiert sind, und wobei Heterocyclyl n (R 1 ) 2 N (O) 2 S and R 1 O- (C 1 -C 6 ) -alkyl, and wherein heterocyclyl n
Oxogruppen trägt. Carries oxo groups.
Ganz besonders bevorzugt sind Verbindungen der allgemeinen Formel (I), worin Q bedeutet einen Rest Q1 , Q2, Q3 oder Q4, Very particular preference is given to compounds of the general formula (I) in which Q denotes a radical Q1, Q2, Q3 or Q4,
X bedeutet Nitro, Halogen, Methyl, Ethyl, n-Propyl, iso-Propyl, Trifluormethyl, Difluormethyl, Chiordifiuormethyl, Dichlorfluormethyl, Trichlormethyl, Pentafluorethyl, Heptafluorisopropyl, Cyclopropyl, Methoxy, Ethoxy, Methylsulfanyl, Methylsulfinyl, Methylsulfonyl, Methoxymethyl, Ethoxymethyl, Methoxyethyl, Methoxyethoxymethyl, Methylthiomethyl, Methylsulfinylmethyl oder Methylsulfonylmethyl, X is nitro, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, chiorofluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, heptafluoroisopropyl, cyclopropyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, Methoxyethoxymethyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl,
W bedeutet Wasserstoff, Chlor oder Methyl, R bedeutet Wasserstoff, W is hydrogen, chlorine or methyl, R is hydrogen,
Rx bedeutet Methyl, Ethyl, n-Propyl, Prop-2-en-1 -yl, Methoxyethyl, Ethoxyethyl oder Methoxyethoxyethyl, RY bedeutet Methyl, Ethyl, n-Propyl, Chlor oder Amino, R x represents methyl, ethyl, n-propyl, prop-2-en-1-yl, methoxyethyl, ethoxyethyl or methoxyethoxyethyl, R Y is methyl, ethyl, n-propyl, chlorine or amino,
Rz bedeutet Methyl, Ethyl, n-Propyl oder Methoxymethyl. L bedeutet eine Brücke ausgewählt aus der Gruppe bestehend aus A1 , A2, A4, A5, A6, A7, A8, A25, A26, A28, A29, A30, A31 , A32, A49, A50, A51 , A53, A55, A57, A59, A61 , A139, A140, A141 , A142, A143, A145, A146, A147, A148, A149, A150, A274, A275, A278, A279, A280, A281 , A282, A283, A284, A285, A286, A363, A364, A365, A366, A367, A368, A369, A370, A371 , A372 und A373, R z is methyl, ethyl, n-propyl or methoxymethyl. L denotes a bridge selected from the group consisting of A1, A2, A4, A5, A6, A7, A8, A25, A26, A28, A29, A30, A31, A32, A49, A50, A51, A53, A55, A57, A59, A61, A139, A140, A141, A142, A143, A145, A146, A147, A148, A149, A150, A274, A275, A278, A279, A280, A281, A282, A283, A284, A285, A286, A363, A364, A365, A366, A367, A368, A369, A370, A371, A372 and A373,
R7, R8, R12, R13, R22 und R23 bedeuten unabhängig voneinander jeweils R 7 , R 8 , R 12 , R 13 , R 22 and R 23 are each independently
Wasserstoff, Halogen, Methyl, Ethyl, n-Propyl, iso-Propyl, Trifiuormethyi, Cyclopropyl, Methoxy, Ethoxy, Methylsulfanyl, Methylsulfinyl, Methylsulfonyl, Methoxymethyl, Ethoxymethyl, Methoxyethyl, Methoxyethoxymethyl, Methylthiomethyl, Is hydrogen, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, cyclopropyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxyethoxymethyl, methylthiomethyl,
Methylsulfinylmethyl oder Methylsulfonylmethyl, Methylsulfinylmethyl or methylsulfonylmethyl,
R9, R10, R14, R15, R16, R17, R20, R21, R24 und R25 bedeuten unabhängig voneinander jeweils Wasserstoff, Halogen, Methyl, Methoxy, Ethoxy oder je zwei geminale R9, R10, R14, R15, R16, R17, R20, R21, R24 und R25 bilden gemeinsam mit dem Kohlenstoffatom, an das sie gebunden sind, eine Carbonylgruppe oder einR 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 are each independently hydrogen, halogen, methyl, methoxy, ethoxy or two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 together with the carbon atom to which they are attached form a carbonyl group or a
Oxim der Formel C=NOR1 oder je zwei geminale R9, R10, R14, R15, R16, R17, R20, R21, R24 und R25 bedeuten ein Acetal der Formel -0-(CH2)2-0-, Oxime of formula C = NOR 1 or two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 is an acetal of the formula -0- (CH 2 ) 2-0-,
R1 bedeutet Wasserstoff, Methyl oder Ethyl, R 1 is hydrogen, methyl or ethyl,
R11, R19, R26 und R27 bedeuten unabhängig voneinander jeweils Wasserstoff oder Methyl, R 11 , R 19 , R 26 and R 27 are each independently hydrogen or methyl,
R28, R29, R30 und R31 bedeuten unabhängig voneinander jeweils Wasserstoff, Nitro, Halogen, Methyl, Ethyl, n-Propyl, iso-Propyl, Trifiuormethyi, Difluormethyl, R 28 , R 29 , R 30 and R 31 independently of one another are each hydrogen, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl,
Chlordifluormethyl, Dichlorfluormethyl, Trichlormethyl, Pentafluorethyl, Heptafluorisopropyl, Cyclopropyl, Methoxy, Ethoxy, Methylsulfanyl, Methylsulfinyl, Methylsulfonyl, Methoxymethyl, Ethoxymethyl, Methoxyethyl, Methoxyethoxymethyl, Methylthiomethyl, Methylsulfinylmethyl oder Methylsulfonylmethyl. In allen nachfolgend genannten Formeln haben die Substituenten und Symbole, sofern nicht anders definiert, dieselbe Bedeutung wie unter Formel (I) beschrieben. Chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, Heptafluoroisopropyl, cyclopropyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxyethoxymethyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl. In all of the formulas below, the substituents and symbols, unless otherwise defined, have the same meaning as described for formula (I).
Erfindungsgemäße Verbindungen, in denen Q für Q1 oder Q2 steht, können Compounds of the invention in which Q is Q1 or Q2 can
beispielsweise nach der in Schema 1 angegebenen Methode durch basenkatalysierte Umsetzung eines Benzoesäurechlorids (II) mit einem 5-Amino-1 -H-1 ,2,4-triazol bzw. 5- Amino-1 H-tetrazol (III) hergestellt werden: Example, by the method indicated in Scheme 1 by base-catalyzed reaction of a benzoic acid chloride (II) with a 5-amino-1-H-1, 2,4-triazole or 5-amino-1 H-tetrazole (III) are prepared:
Schema 1 Scheme 1
(III) (II) (l) Darin steht B für CH oder N. Die Benzoesäurechloride der Formel (II)  (III) (II) (1) where B is CH or N. The benzoic acid chlorides of the formula (II)
beziehungsweise die ihnen zugrunde liegenden Benzoesäuren sind grundsätzlich bekannt und können beispielsweise gemäß den in DE 19532312 und WO 98/12192 beschriebenen Methoden hergestellt werden. Erfindungsgemäße Verbindungen, in denen Q für Q1 oder Q2 steht, können auch nach der in Schema 2 angegebenen Methode durch Umsetzung einer Benzoesäure der Formel (IV) mit einem 5-Amino-1 -H-1 ,2,4-triazol bzw. 5-Amino-1 H-tetrazol (III) hergestellt werden: Schema 2 or their underlying benzoic acids are basically known and can be prepared, for example, according to the methods described in DE 19532312 and WO 98/12192. Compounds according to the invention in which Q represents Q1 or Q2 can also be prepared by the method given in Scheme 2 by reacting a benzoic acid of the formula (IV) with a 5-amino-1 -H-1, 2,4-triazole or 5 Amino-1 H-tetrazole (III) can be prepared: Scheme 2
(Hl) (IV) (i) (Hl) (IV) (i)
Für die Aktivierung können wasserentziehende Reagenzien, die üblicherweise für Amidierungsreaktionen, wie z. B. 1 , 1 '-Carbonyldiimidazol (CDI), Dicyclohexyl- carbodiimid (DCC), 2,4,6-Tripropyl-1 ,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc. eingesetzt werden. For the activation, dehydrating reagents commonly used for amidation reactions, such. B. 1, 1 'carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 2,4,6-tripropyl-1, 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc. are used.
Erfindungsgemäße Verbindungen, in denen Q für Q1 oder Q2 steht, können auch nach der in Schema 3 angegebenen Methode durch Umsetzung eines N-(1 H-1 ,2,4- triazol-5-yl)benzamids oder eines N-(1 H-tetrazol-5-yl)benzamids hergestellt werden Compounds of the invention in which Q is Q1 or Q2 can also be prepared by the method given in Scheme 3 by reacting an N- (1H-1, 2,4-triazol-5-yl) benzamide or an N- (1H tetrazol-5-yl) benzamide
Schema 3 Scheme 3
(V) (I) (V) (I)
Für diese oben genannte Reaktion können Alkylierungsmittel wie z. B. Alkyl- halogenide, -sulfonate oder Dialkylsulfate in Gegenwart einer Base eingesetzt werden. For this reaction above alkylating agents such as. B. alkyl halides, sulfonates or dialkyl sulfates can be used in the presence of a base.
Die 5-Amino-1 H-tetrazole der Formel (III) sind entweder käuflich erhältlich oder können analog zu literaturbekannten Methoden hergestellt werden. Beispielsweise können substituierte 5-Aminotetrazole nach der in Journal of the American Chemical Society (1954), 76, 923-924 beschriebenen Methode aus Amino-tetrazol hergestellt werden: The 5-amino-1H-tetrazoles of the formula (III) are either commercially available or can be prepared analogously to methods known from the literature. For example, substituted 5-aminotetrazoles can be prepared from amino-tetrazole by the method described in Journal of the American Chemical Society (1954), 76, 923-924:
In der vorstehend genannten Reaktion bedeutet X eine Abgangsgruppe wie lod.In the above reaction, X represents a leaving group such as iodine.
Substituierte 5-Aminotetrazole können zum Beispiel auch wie in Journal of the American Chemical Society (1954) 76, 88-89 beschrieben, synthetisiert werden: Substituted 5-aminotetrazoles can also be synthesized, for example, as described in Journal of the American Chemical Society (1954) 76, 88-89:
Die 5-Amino-1 H-triazole der Formel (III) sind entweder käuflich erhältlich oder können analog zu literaturbekannten Methoden hergestellt werden. Beispielsweise können substituierte 5-Aminotriazole nach der in Zeitschrift für Chemie (1990), 30(12), 436 - 437 beschriebenen Methode aus Aminotriazol hergestellt werden: The 5-amino-1H-triazoles of the formula (III) are either commercially available or can be prepared analogously to methods known from the literature. For example, substituted 5-aminotriazoles can be prepared from aminotriazole according to the method described in Zeitschrift fur Chemie (1990), 30 (12), 436-437:
In der vorstehend genannten Reaktion bedeutet X eine Abgangsgruppe wie lod.In the above reaction, X represents a leaving group such as iodine.
Substituierte 5-Aminotriazole können auch zum Beispiel wie in Chemische Berichte (1964), 97(2), 396-404 beschrieben synthetisiert werden: Substituted 5-aminotriazoles can also be synthesized, for example, as described in Chemische Berichte (1964), 97 (2), 396-404:
Substituierte 5-Aminotriazole können auch zum Beispiel wie in Angewandte Chemie Substituted 5-aminotriazoles can also be used, for example, as in Angewandte Chemie
(1963), 75, 918 beschrieben, synthetisiert werden: (1963), 75, 918, are synthesized:
Erfindungsgemäße Verbindungen, in denen Q für Q3 steht, können beispielsweise nach der in Schema 4 angegebenen Methode durch basenkatalysierte Umsetzung eines Benzoesäurechlorids (II) mit einem 4-Amino-1 ,2,5-oxadiazol (VI) hergestellt werden: Compounds according to the invention in which Q is Q3 can be prepared, for example, by the method indicated in Scheme 4 by base-catalyzed reaction of a benzoic acid chloride (II) with a 4-amino-1,2,5-oxadiazole (VI):
Schema 4 Scheme 4
Erfindungsgemäße Verbindungen können auch nach der in Schema 5 angegebenen Methode durch Umsetzung einer Benzoesäure der Formel (IV) mit einem 4-Amino- 1 ,2,5-oxadiazol (VI) hergestellt werden: Compounds according to the invention can also be prepared by the method given in Scheme 5 by reacting a benzoic acid of the formula (IV) with a 4-amino-1,2,5-oxadiazole (VI):
Schema 5 Scheme 5
(VI) (IV) Für die Aktivierung können wasserentziehende Reagenzien die üblicherweise für Amidierungsreaktionen, wie z. B. 1 , '-Carbonyldiimidazol (CDI), Dicyclohexyl- carbodiimid (DCC), 2,4,6-Tripropyl-1 ,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc., eingesetzt werden. (VI) (IV) For the activation dehydrating reagents usually for amidation reactions such. B. 1, ' -Carbonyldiimidazol (CDI), dicyclohexylcarbodiimide (DCC), 2,4,6-tripropyl-1, 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc ., be used.
Die 4-Amino-1 ,2,5-oxadiazole der Formel (VI) sind entweder käuflich erhältlich oder bekannt oder können analog zu literaturbekannten Methoden hergestellt werden. The 4-amino-1, 2,5-oxadiazoles of the formula (VI) are either commercially available or known or can be prepared analogously to methods known from the literature.
Beispielsweise können 3-Alkyl-4-amino-1 ,2,5-oxadiazole nach der in Russian For example, 3-alkyl-4-amino-1,2,5-oxadiazoles can be prepared according to the method described in Russian
Chemical Bulletin, Int. Ed., Vol. 54, No. 4, S. 1032-1037 (2005) beschriebenen Chemical Bulletin, Int. Ed., Vol. 54, no. 4, pp. 1032-1037 (2005)
Methode aus ß-Ketoestern hergestellt werden: Method to be prepared from β-ketoesters:
3-Aryl-4-amino-1 ,2,5-oxadiazole können zum Beispiel wie in Russian Chemical Bulletin, 54(4), 1057-1059, (2005) oder Indian Journal of Chemistry, Section B: For example, 3-aryl-4-amino-1, 2,5-oxadiazoles can be synthesized as described in Russian Chemical Bulletin, 54 (4), 1057-1059, (2005) or Indian Journal of Chemistry, Section B:
Organic Chemistry Including Medicinai Chemistry, 26B(7), 690-2, (1987) beschrieben, synthetisiert werden:  Organic Chemistry Including Medicinal Chemistry, 26B (7), 690-2, (1987).
3-Amino-4-Halogen-1 ,2,5-oxadiazole können beispielsweise nach der in Heteroatom Chemistry 15(3), 199-207 (2004) beschrieben Methode aus dem käuflich erhältlichen 3,4-Diamino-1 ,2,5-oxadiazol durch eine Sandmeyer-Reaktion hergestellt werden:  3-Amino-4-halo-1, 2,5-oxadiazoles can be prepared, for example, from the commercially available 3,4-diamino-1, 2.5 by the method described in Heteroatom Chemistry 15 (3), 199-207 (2004) Oxadiazole be prepared by a Sandmeyer reaction:
Nucleophile Reste RY können wie in Journal of Chemica! Research, Synopses, (6), 190, 1985 oder in oder Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, (9), 2086-8, 1986 oder in Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya), 53(3), 596-614, 2004 beschrieben, durch Substitution der Austrittsgruppe L in 3-Amino-1 ,2,5-oxadiazolen eingeführt werden. L steht für eine Abgangsgruppe wie z. B. Chlor, Brom, Jod, Mesyloxy, Tosyloxy, Trifluorsulfonyloxy etc.. Nucleophilic radicals R Y can be found in Journal of Chemica! Research, Synopses, (6), 190, 1985 or in or Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, (9), 2086-8, 1986 or in Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya), 53 (3 ), 596-614, 2004, by substitution of the leaving group L in 3-amino-1, 2,5-oxadiazoles. L stands for a leaving group such. Chlorine, bromine, iodine, mesyloxy, tosyloxy, trifluorosulfonyloxy etc.
Erfindungsgemäße Verbindungen, in denen Q für Q4 steht, können beispielsweise nach der in Schema 6 angegebenen Methode durch basenkatalysierte Umsetzung eines Benzoesäurechlorids (II) mit einem 2-Amino-1 ,3,4-oxadiazol (VII) hergestellt werden: Compounds according to the invention in which Q is Q4 can be prepared, for example, by the method indicated in scheme 6 by base-catalyzed reaction of a benzoic acid chloride (II) with a 2-amino-1,3,4-oxadiazole (VII):
Schema 6 Scheme 6
(VII) (II)  (VII) (II)
Erfindungsgemäße Verbindungen können auch nach der in Schema 7 angegebenen Methode durch Umsetzung einer Benzoesäure der Formel (IV) mit einem 2-Amino- 1 ,3,4-oxadiazol (VII) hergestellt werden: Schema 7 Compounds of the invention can also be prepared by the method given in Scheme 7 by reacting a benzoic acid of the formula (IV) with a 2-amino-1,3,4-oxadiazole (VII): Scheme 7
(VII) (SV) (i) (VII) (SV) (i)
Für die Aktivierung können wasserentziehende Reagenzien, die üblicherweise für Amidierungsreaktionen, wie z. B. 1 , 1 '-Carbonyldiimidazol (CDI), Dicyclohexyl- carbodiimid (DCC), 2,4,6-Tripropyl-1 ,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc. eingesetzt werden. For the activation, dehydrating reagents commonly used for amidation reactions, such. B. 1, 1 'carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 2,4,6-tripropyl-1, 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc. are used.
Erfindungsgemäße Verbindungen können auch nach der in Schema 8 angegebenen Methode durch Cyciisierung einer Verbindung der Formel VI I I hergestellt werden: Compounds according to the invention can also be prepared by the method indicated in Scheme 8 by cyclization of a compound of the formula VI I I:
Schema 8 Scheme 8
(VI I I) (I) (VI II) (I)
Die Cyciisierung kann gemäß der in Synth. Commun. 31 (12), 1907-1912 (2001 ) oder der in Indian J. Chem., Section B: Organic Chemistry Including Medicinal Chemistry; Vol. 43 (10), 2170-2174 (2004) beschriebenen Methoden durchgeführt werden. Schema 9 The cyclization can be carried out according to the procedure described in Synth. Commun. 31 (12), 1907-1912 (2001) or Indian J. Chem., Section B: Organic Chemistry Including Medicinal Chemistry; Vol. 43 (10), 2170-2174 (2004). Scheme 9
(IX) (X) (VIII)  (IX) (X) (VIII)
Die in Schema 8 eingesetzte Verbindung der Formel VIII kann durch Umsetzung eines Acylisothiocyanats der Formel X mit einem Hydrazid der Formel IX gemäß der von in Synth. Commun. 25(12), 1885-1892 (1995) beschriebenen Methode hergestellt werden. The compound of formula VIII employed in scheme 8 can be prepared by reacting an acyl isothiocyanate of formula X with a hydrazide of formula IX according to the method described in Synth. Commun. 25 (12), 1885-1892 (1995).
Erfindungsgemäße Verbindungen, in denen der Substituent R nicht Wasserstoff bedeutet, können beispielsweise nach der in Schema 10 angegebenen Methode durch Umsetzung eines N-(1 ,2,5-Oxadiazol-3-yl)-, N-(1 ,3,4-Oxadiazol-2-yl), N-(Tetrazol-S-yl)- oder N-(Triazol-5-yl)bicycloarylcarbonsäureamids (I) mit einer Verbindung der allgemeinen Formel (XI) hergestellt werden: Compounds according to the invention in which the substituent R is not hydrogen can be synthesized, for example, by the reaction of an N- (1,2,5-oxadiazol-3-yl) -, N- (1, 3,4-) in the manner indicated in Scheme 10. Oxadiazol-2-yl), N- (tetrazol-S-yl) - or N- (triazol-5-yl) bicycloarylcarbonsäureamids (I) are prepared with a compound of general formula (XI):
Schema 10 Scheme 10
(l) (XI) (l)  (l) (XI) (l)
Die Verbindungen der Formel (XI), bei denen L eine Abgangsgruppe wie z. B. Chlor, Brom, Jod, Methylsulfonyloxy, Tosyloxy oder Trifluorsulfonyloxy bedeutet, sind entweder käuflich oder können nach bekannten in der Literatur beschriebenen The compounds of the formula (XI) in which L is a leaving group such as. Chlorine, bromine, iodine, methylsulfonyloxy, tosyloxy or trifluorosulfonyloxy, are either commercially available or may be as described in the literature
Methoden hergestellt werden. Methods are produced.
Erfindungsgemäße Verbindungen können auch nach der in Schema 1 1 angegebenen Methode durch Umsetzung eines Amins der Formel (XII) mit einem Säurechlorid (II), wie zum Beispie! in J. Hei. Chem. (1972), 9 (1 ), 107-109) beschrieben, hergestellt werden: Compounds according to the invention can also be prepared by the method given in Scheme 1 1 by reacting an amine of the formula (XII) with an acid chloride (II), how the example! in J. Hei. Chem. (1972), 9 (1), 107-109).
(XII) (Ii) (i)  (XII) (ii) (i)
Erfindungsgemäße Verbindungen können auch nach der in Schema 12 angegeb Methode durch Umsetzung eines Amins der Formel (XII) mit einer Säure der Form (IV) hergestellt werden: Compounds of the invention can also be prepared by the method given in Scheme 12 by reacting an amine of formula (XII) with an acid of the form (IV):
(XII) (IV) (I)  (XII) (IV) (I)
Für die Aktivierung können wasserentziehende Reagenzien, die üblicherweise für Amidierungsreaktionen, wie z. B. 1 ,1 '-Carbonyldiimidazol (CDI), Dicyclohexyl- carbodiimid (DCC), 2,4,6-Tripropyl-1 ,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc. eingesetzt werden. For the activation, dehydrating reagents commonly used for amidation reactions, such. B. 1, 1 'carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 2,4,6-tripropyl-1, 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc. are used.
Die Amine der Formel (XII) sind entweder käuflich oder in der Literatur bekannt oder können beispielsweise nach der in Schema 13 beschriebenen Methode durch basenkatalysierte Alkylierung oder durch reduktive Alkylierung oder nach der in Schema 14 beschriebenen Methode durch nucleophile Substitution einer Abgangsgruppe L wie beispielsweise Chlor durch Amine R-NH2 hergestellt werden. Schema 13 The amines of the formula (XII) are either commercially available or known in the literature or can, for example, by the method described in Scheme 13 by base-catalyzed alkylation or by reductive alkylation or by the method described in Scheme 14 by nucleophilic substitution of a leaving group L such as chlorine Amine R-NH2 can be produced. Scheme 13
(Xl l l) (XII)  (XII) (XII)
Schema 14 Scheme 14
L R" 2 N L R " 2 N
R  R
(XIV) (XII) Die Amine der Formel (XII) können auch durch Cyclisierungsreaktionen wie zum (XIV) (XII) The amines of the formula (XII) may also be obtained by cyclization reactions such as
Beispiel in J. Org. Chem. 73(10), 3738-3744 (2008) für Q = Q1 oder in Buletinul Institutului Politehnic din lasi (1974), 20(1 -2), 95-99 oder in J. Org. Chem. 67(21 ), 7361 -7364 (2002) für Q = Q4 beschrieben, hergestellt werden. Es kann zweckmäßig sein, Reaktionsschritte in ihrer Reihenfolge zu ändern. So sind Benzoesäuren, die ein Sulfoxid tragen, nicht ohne weiteres in ihre Säurechloride zu überführen. Hier bietet sich an, zunächst auf Thioether-Stufe das Amid zu herzustellen und danach den Thioether zum Sulfoxid zu oxidieren. Die Aufarbeitung der jeweiligen Reaktionsmischungen erfolgt in der Regel nach bekannten Verfahren, beispielsweise durch Kristallisation, wässrig-extraktive Example in J. Org. Chem. 73 (10), 3738-3744 (2008) for Q = Q1 or in Buletinul Institutului Politehnic din lasi (1974), 20 (1-2), 95-99 or in J. Org. Chem. 67 (21), 7361-7364 (2002) for Q = Q4. It may be convenient to change reaction steps in order. Thus, benzoic acids carrying a sulfoxide are not readily converted into their acid chlorides. Here it is advisable to first produce the amide on the thioether stage and then to oxidize the thioether to the sulfoxide. The work-up of the respective reaction mixtures is generally carried out by known methods, for example by crystallization, aqueous-extractive
Aufarbeitung, durch chromatographische Methoden oder durch Kombination dieser Methoden. Kollektionen aus Verbindungen der Formel (I) und/oder deren Salzen, die nach den oben genannten Reaktionen synthetisiert werden können, können auch in Work-up, by chromatographic methods or by combination of these methods. Collections of compounds of the formula (I) and / or their salts, which can be synthesized after the abovementioned reactions, can also be found in
parallelisierter Weise hergestellt werden, wobei dies in manueller, teilweise be prepared in a parallelized manner, this manual, in part
automatisierter oder vollständig automatisierter Weise geschehen kann. Dabei ist es beispielsweise möglich, die Reaktionsdurchführung, die Aufarbeitung oder die automated or completely automated way. It is possible, for example, the reaction procedure, the work-up or the
Reinigung der Produkte bzw. Zwischenstufen zu automatisieren. Insgesamt wird hierunter eine Vorgehensweise verstanden, wie sie beispielsweise durch D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (Herausgeber Günther Jung), Verlag Wiley 1999, auf den Seiten 1 bis 34 beschrieben ist. Zur parallelisierten Reaktionsdurchführung und Aufarbeitung können eine Reihe von im Handel erhältlichen Geräten verwendet werden, beispielsweise Calpyso- Reaktionsblöcke (Caylpso reaction blocks) der Firma Barnstead International, Automate cleaning of products or intermediates. Overall will be This is understood to mean a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (published by Günther Jung), Verlag Wiley 1999, pages 1 to 34. For the parallelized reaction procedure and workup, a number of commercially available devices can be used, for example Calypyso reaction blocks (Caylpso reaction blocks) from Barnstead International,
Dubuque, Iowa 52004-0797, USA oder Reaktionsstationen (reaction stations) der Firma Radleys, Shirehill, Saffron Waiden, Essex, CB 11 3AZ, England oder Dubuque, Iowa 52004-0797, USA or reaction stations from Radleys, Shirehill, Saffron Waiden, Essex, CB 11 3AZ, England or
MultiPROBE Automated Workstations der Firma Perkin Elmar, Waltham, MultiPROBE Automated Workstations from Perkin Elmar, Waltham,
Massachusetts 02451 , USA. Für die parallelisierte Aufreinigung von Verbindungen der allgemeinen Formel (I) und deren Salzen beziehungsweise von bei der Herstellung anfallenden Zwischenprodukten stehen unter anderem Chromatographieapparaturen zur Verfügung, beispielsweise der Firma ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.  Massachusetts 02451, United States. For the parallelized purification of compounds of the general formula (I) and their salts or of intermediates obtained during the preparation, among others, chromatography apparatuses are available, for example the company ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.
Die aufgeführten Apparaturen führen zu einer modularen Vorgehensweise, bei der die einzelnen Arbeitsschritte automatisiert sind, zwischen den Arbeitsschritten jedoch manuelle Operationen durchgeführt werden müssen. Dies kann durch den Einsatz von teilweise oder vollständig integrierten Automationssystemen umgangen werden, bei denen die jeweiligen Automationsmodule beispielsweise durch Roboter bedient werden. Derartige Automationssysteme können zum Beispiel von der Firma Caliper, Hopkinton, MA 01748, USA bezogen werden. Die Durchführung einzelner oder mehrerer Syntheseschritte kann durch den Einsatz von Polymer-supported reagents/Scavanger-Harze unterstützt werden. In der The listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed. This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots. Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA. The implementation of single or multiple synthetic steps can be supported by the use of polymer-supported reagents / Scavanger resins. In the
Fachliteratur sind eine Reihe von Versuchsprotokollen beschrieben, beispielsweise in ChemFiles, Vol. 4, No. 1 , Polymer-Supported Scavengers and Reagents for Solution- Phase Synthesis (Sigma-Aldrich). Technical literature describes a number of experimental protocols, for example in ChemFiles, Vol. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).
Neben den hier beschriebenen Methoden kann die Herstellung von Verbindungen der allgemeinen Formel (I) und deren Salzen vollständig oder partiell durch Festphasen unterstützte Methoden erfolgen. Zu diesem Zweck werden einzelne Zwischenstufen oder alle Zwischenstufen der Synthese oder einer für die entsprechende Vorgehensweise angepassten Synthese an ein Syntheseharz gebunden. Festphasen- unterstützte Synthesemethoden sind in der Fachliteratur hinreichend beschrieben, z.B. Barry A. Bunin in "The Combinatorial Index", Verlag Academic Press, 1998 und In addition to the methods described herein, the preparation of compounds of general formula (I) and their salts can be carried out fully or partially by solid-phase assisted methods. For this purpose, individual intermediates or all intermediates of the synthesis or one for the corresponding Approach adapted synthesis bound to a synthetic resin. Solid-phase assisted synthesis methods are well described in the literature, eg Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998 and
Combinatorial Chemistry - Synthesis, Analysis, Screening (Herausgeber Günther Jung), Verlag Wiley, 1999. Die Verwendung von Festphasen- unterstützten Combinatorial Chemistry - Synthesis, Analysis, Screening (published by Günther Jung), published by Wiley, 1999. The use of solid phase assisted
Synthesemethoden erlaubt eine Reihe von literaturbekannten Protokollen, die wiederum manuell oder automatisiert ausgeführt werden können. Die Reaktionen können beispielsweise mittels IRORI-Technologie in Mikroreaktoren (microreactors) der Firma Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA durchgeführt werden. Synthesis methods allow a number of protocols known from the literature, which in turn can be carried out manually or automatically. The reactions can be carried out, for example, by means of IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
Sowohl an fester als auch in flüssiger Phase kann die Durchführung einzelner oder mehrerer Syntheseschritte durch den Einsatz der Mikrowellen-Technologie unterstützt werden. In der Fachliteratur sind eine Reihe von Versuchsprotokollen beschrieben, beispielsweise in Microwaves in Organic and Medicinal Chemistry (Herausgeber C. O. Kappe und a. Stadler), Verlag Wiley, 2005. Both solid and liquid phases can be supported by the implementation of single or multiple synthetic steps through the use of microwave technology. A number of experimental protocols are described in the specialist literature, for example in Microwaves in Organic and Medicinal Chemistry (publishers C. O. Kappe and A. Stadler), Verlag Wiley, 2005.
Die Herstellung gemäß der hier beschriebenen Verfahren liefert Verbindungen der Formel (I) und deren Salze in Form von Substanzkollektionen, die Bibliotheken genannt werden. Gegenstand der vorliegenden Erfindung sind auch Bibliotheken, die mindestens zwei Verbindungen der Formel (I) und deren Salzen enthalten. The preparation according to the methods described herein provides compounds of formula (I) and their salts in the form of substance collections called libraries. The present invention also provides libraries containing at least two compounds of formula (I) and their salts.
Die erfindungsgemäßen Verbindungen der Formel (I) (und/oder deren Salze), im folgenden zusammen als„erfindungsgemäße Verbindungen" bezeichnet, weisen eine ausgezeichnete herbizide Wirksamkeit gegen ein breites Spektrum wirtschaftlich wichtiger mono- und dikotyler annueller Schadpflanzen auf. Auch schwer bekämpf bare perennierende Schad pflanzen, die aus Rhizomen, Wurzelstöcken oder anderen Dauerorganen austreiben, werden durch die Wirkstoffe gut erfaßt. Gegenstand der vorliegenden Erfindung ist daher auch ein Verfahren zur Bekämpfung von unerwünschten Pflanzen oder zur Wachstumsregulierung von Pflanzen, vorzugsweise in Pflanzenkulturen, worin eine oder mehrere erfindungsgemäße The compounds of the formula (I) according to the invention (and / or their salts), together referred to as "compounds according to the invention", have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants The present invention therefore also relates to a method for controlling undesirable plants or regulating the growth of plants, preferably in plant crops, wherein one or more of the plants according to the invention are plants which are expectorant from rhizomes, rhizomes or other permanent organs
Verbindung(en) auf die Pflanzen (z.B. Schadpflanzen wie mono- oder dikotyle Compound (s) on the plants (e.g., weeds such as mono- or dicotyledons
Unkräuter oder unerwünschte Kulturpflanzen), das Saatgut (z.B. Körner, Samen oder vegetative Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen) oder die Fläche, auf der die Pflanzen wachsen (z.B. die Anbaufläche), ausgebracht werden. Dabei können die erfindungsgemäßen Verbindungen z.B. im Vorsaat- (ggf. auch durch Einarbeitung in den Boden), Vorauflauf- oder Nachauflaufverfahren ausgebracht werden. Im einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen Unkrautflora genannt, die durch die erfindungsgemäßen Verbindungen kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll. Monokotyle Schadpflanzen der Gattungen: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyl- octenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. Weeds or unwanted crops), the seeds (eg grains, seeds or vegetative propagules such as tubers or sprouts with buds) or the area on which the plants grow (eg the acreage). The compounds according to the invention can be applied, for example, in pre-sowing (optionally also by incorporation into the soil), pre-emergence or postemergence process. Specifically, by way of example, some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species. Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyl octenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera , Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
Dikotyle Unkräuter der Gattungen: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum,
Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
Werden die erfindungsgemäßen Verbindungen vor dem Keimen auf die Erdoberfläche appliziert, so wird entweder das Auflaufen der Unkrautkeimlinge vollständig verhindert oder die Unkräuter wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen If the compounds according to the invention are applied to the surface of the earth prior to germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then stop their growth and finally die after three to four weeks
vollkommen ab. completely off.
Bei Applikation der Wirkstoffe auf die grünen Pflanzenteile im Nachauflaufverfahren tritt nach der Behandlung Wachstumsstop ein und die Schadpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so dass auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird. Upon application of the active ingredients to the green parts of the plants post-emergence, growth stops after the treatment and the harmful plants remain in the growth stage present at the time of application or die a certain time completely, so that in this way harmful to the crops weed competition is eliminated very early and sustainable.
Obgleich die erfindungsgemäßen Verbindungen eine ausgezeichnete herbizide Although the compounds of the invention are excellent herbicides
Aktivität gegenüber mono- und dikotylen Unkräutern aufweisen, werden Kulturpflanzen wirtschaftlich bedeutender Kulturen z.B. dikotyler Kulturen der Gattungen Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Have activity against monocotyledonous and dicotyledonous weeds, crops of economically important crops, e.g. dicotyledonous cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium,
Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, oder monokotyler Kulturen der Gattungen Allium, Ananas, Asparagus, Avena, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the genera Allium, Pineapple, Asparagus, Avena,
Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, insbesondere Zea und Triticum, abhängig von der Struktur der jeweiligen Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, especially Zea and Triticum, depending on the structure of each
erfindungsgemäßen Verbindung und deren Aufwandmenge nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in Compound of the invention and its application rate only insignificantly damaged or not at all. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in
Pflanzenkulturen wie landwirtschaftlichen Nutzpflanzungen oder Zierpflanzungen. Crops such as agricultural crops or ornamental plantings.
Darüberhinaus weisen die erfindungsgemäßen Verbindungen (abhängig von ihrer jeweiligen Struktur und der ausgebrachten Aufwandmenge) hervorragende In addition, the compounds of the present invention (depending on their respective structure and applied application rate) are excellent
wachstumsregulatorische Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten growth regulatory properties in crop plants. They regulate the plant's metabolism and can thus be targeted
Beeinflussung von Pflanzeninhaltsstoffen und zur Ernteerleichterung wie z.B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Desweiteren eignen sie sich auch zur generellen Steuerung und Hemmung von unerwünschtem vegetativen Wachstum, ohne dabei die Pflanzen abzutöten. Eine Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da beispielsweise die Lagerbildung hierdurch verringert oder völlig verhindert werden kann.  Influence of phytonutrients and harvest relief, e.g. be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, since, for example, storage formation can thereby be reduced or completely prevented.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die Wirkstoffe auch zur Bekämpfung von Schadpflanzen in Kulturen von gentechnisch oder durch konventionelle Mutagenese veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Because of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants. The transgenic plants are usually characterized by particular advantageous properties, for example, by resistance to certain pesticides, especially certain herbicides, resistance to Plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special
Eigenschaften betreffen z. B. das Erntegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Ernteguts bekannt. Properties concern z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients. Thus, transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
Bevorzugt bezüglich transgener Kulturen ist die Anwendung der erfindungsgemäßen Verbindungen in wirtschaftlich bedeutenden transgenen Kulturen von Nutz- und Preferred with respect to transgenic cultures is the use of the compounds of the invention in economically important transgenic crops of useful and
Zierpflanzen, z. B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten .Vorzugsweise können die erfindungsgemäßen Verbindungen als Herbizide in Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. Ornamental plants, z. As cereals such as wheat, barley, rye, oats, millet, rice and corn or cultures of sugar beet, cotton, soybeans, rapeseed, potato, tomato, pea and other vegetables. Preferably, the compounds of the invention can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or
gentechnisch resistent gemacht worden sind. have been made genetically resistant.
Bevorzugt ist die Anwendung der erfindungsgemäßen Verbindungen oder deren Salze in wirtschaftlich bedeutenden transgenen Kulturen von Nutz-und Zierpflanzen, z. B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis, Maniok und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten. Vorzugsweise können die erfindungsgemäßen Verbindungen als Herbizide in Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. Preferably, the application of the compounds of the invention or their salts in economically important transgenic crops of useful and ornamental plants, eg. As cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables. Preferably, the compounds according to the invention can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
Herkömmliche Wege zur Herstellung neuer Pflanzen, die im Vergleich zu bisher vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen Conventional ways of producing new plants that have modified properties compared to previously occurring plants exist
beispielsweise in klassischen Züchtungsverfahren und der Erzeugung von Mutanten. Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe for example, in classical breeding methods and the generation of mutants. Alternatively, new plants with altered properties can help
gentechnischer Verfahren erzeugt werden (siehe z. B. EP-A-0221044, EP-A-0131624). Beschrieben wurden beispielsweise in mehreren Fällen genetic engineering methods are produced (see eg EP-A-0221044, EP-A-0131624). For example, several cases have been described
gentechnische Veränderungen von Kulturpflanzen zwecks Modifikation der in den Pflanzen synthetisierten Stärke (z. B. WO 92/1 1376, WO 92/14827, WO 91/19806), transgene Kulturpflanzen, welche gegen bestimmte Herbizide vom Typ genetic engineering of crops for modification of the starch synthesized in the plants (eg WO 92/1 1376, WO 92/14827, WO 91/19806), transgenic crops which are resistant to certain herbicides of the type
Glufosinate (vgl. z. B. EP-A-0242236, EP-A-242246) oder Glyphosate  Glufosinate (see, for example, EP-A-0242236, EP-A-242246) or glyphosate
(WO 92/00377) oder der Sulfonylharnstoffe (EP-A-0257993, US-A-50 3659) resistent sind,  (WO 92/00377) or the sulfonylureas (EP-A-0257993, US-A-50 3659) are resistant,
transgene Kulturpflanzen, beispielsweise Baumwolle, mit der Fähigkeit Bacillus thuringiensis-Toxine (Bt-Toxine) zu produzieren, welche die  Transgenic crops, such as cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which the
Pflanzen gegen bestimmte Schädlinge resistent machen (EP-A-0142924, EP-A-0 93259).  Make plants resistant to certain pests (EP-A-0142924, EP-A-0 93259).
transgene Kulturpflanzen mit modifizierter Fettsäurezusammensetzung (WO 91/13972).  Transgenic crop plants with modified fatty acid composition (WO 91/13972).
gentechnisch veränderte Kulturpflanzen mit neuen Inhalts- oder  genetically modified crops with new content or
Sekundärstoffen z. B. neuen Phytoalexinen, die eine erhöhte  Secondary materials z. B. new phytoalexins, which increased one
Krankheitsresistenz verursachen (EPA 309862, EPA0464461 )  Disease resistance cause (EPA 309862, EPA0464461)
gentechnisch veränderte Pflanzen mit reduzierter Photorespiration, die höhere Erträge und höhere Stresstoleranz aufweisen (EPA 0305398).  genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance (EPA 0305398).
Transgene Kulturpflanzen, die pharmazeutisch oder diagnostisch wichtige Proteine produzieren („molecular pharming")  Transgenic crop plants that produce pharmaceutically or diagnostically important proteins ("molecular pharming")
transgene Kulturpflanzen, die sich durch höhere Erträge oder bessere Qualität auszeichnen  Transgenic crops that are characterized by higher yields or better quality
transgene Kulturpflanzen die sich durch eine Kombinationen z. B. der o. g. neuen Eigenschaften auszeichnen („gene stacking")  transgenic crops characterized by a combination z. B. the o. G. characterize new properties ("gene stacking")
Zahlreiche molekularbiologische Techniken, mit denen neue transgene Pflanzen mit veränderten Eigenschaften hergestellt werden können, sind im Prinzip bekannt, siehe z. B. I. Potrykus und G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, oder Christou, "Trends in Plant Science" 1 (1996) 423-431 ). Numerous molecular biological techniques that can be used to produce novel transgenic plants with altered properties are known in principle. B. I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, "Trends in Plant Science" 1 (1996) 423-431).
Für derartige gentechnische Manipulationen können Nucleinsäuremoleküle in For such genetic manipulations, nucleic acid molecules can be used in
Plasmide eingebracht werden, die eine Mutagenese oder eine Sequenzveränderung durch Rekombination von DNA-Sequenzen erlauben. Mit Hilfe von Standardverfahren können z. B. Basenaustausche vorgenommen, Teilsequenzen entfernt oder natürliche oder synthetische Sequenzen hinzugefügt werden. Für die Verbindung der DNA- Fragmente untereinander können an die Fragmente Adaptoren oder Linker angesetzt werden, siehe z. B. Sambrook ei al., 1989, Molecular Cioning, A Laboratory Manual, 2. Aufl. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, oder Winnacker "Gene und Klone", VCH Weinheim 2. Auflage 1996 Die Herstellung von Pflanzenzellen mit einer verringerten Aktivität eines Genprodukts kann beispielsweise erzielt werden durch die Expression mindestens einer Plasmids are introduced which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments be, see, for. Sambrook et al., 1989, Molecular Cioning, A Laboratory Manual, 2nd Ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996 The production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one
entsprechenden antisense-RNA, einer sense-RNA zur Erzielung eines corresponding antisense RNA, a sense RNA to obtain a
Cosuppressionseffektes oder die Expression mindestens eines entsprechend konstruierten Ribozyms, das spezifisch Transkripte des obengenannten Genprodukts spaltet. Hierzu können zum einen DNA-Moleküle verwendet werden, die die gesamte codierende Sequenz eines Genprodukts einschließlich eventuell vorhandener flankierender Sequenzen umfassen, als auch DNA-Moleküle, die nur Teile der codierenden Sequenz umfassen, wobei diese Teile lang genug sein müssen, um in den Zellen einen antisense- Effekt zu bewirken. Möglich ist auch die Verwendung von DNA-Sequenzen, die einen hohen Grad an Homologie zu den codiereden Sequenzen eines Genprodukts aufweisen, aber nicht vollkommen identisch sind. Cosuppressionseffektes or the expression of at least one appropriately engineered ribozyme that specifically cleaves transcripts of the above gene product. For this purpose, DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
Bei der Expression von Nucleinsäuremolekülen in Pflanzen kann das synthetisierte Protein in jedem beliebigen Kompartiment der pflanzlichen Zelle lokalisiert sein. Um aber die Lokalisation in einem bestimmten Kompartiment zu erreichen, kann z. B. die codierende Region mit DNA-Sequenzen verknüpft werden, die die Lokalisierung in einem bestimmten Kompartiment gewährleisten. Derartige Sequenzen sind dem Fachmann bekannt (siehe beispielsweise Braun et al., EMBO J. 1 1 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad. Sei. USA 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991 ), 95-106). Die Expression der Nukleinsäuremoleküle kann auch in den In the expression of nucleic acid molecules in plants, the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z. For example, the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known in the art (see, for example, Braun et al., EMBO J. 1 1 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106). Expression of the nucleic acid molecules can also be found in the
Organellen der Pflanzenzellen stattfinden. Organelles of the plant cells take place.
Die transgenen Pflanzenzellen können nach bekannten Techniken zu ganzen Pflanzen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen Pflanzenspezies handeln, d.h., sowohl monokotyle als auch dikotyle Pflanzen. The transgenic plant cells can be regenerated to whole plants by known techniques. The transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
So sind transgene Pflanzen erhältlich, die veränderte Eigenschaften durch Thus, transgenic plants are available, the altered properties by
Überexpression, Suppression oder Inhibierung homologer (= natürlicher) Gene oder Gensequenzen oder Expression heterologer (= fremder) Gene oder Gensequenzen aufweisen. Overexpression, suppression or inhibition of homologous (= natural) genes or Gene sequences or expression of heterologous (= foreign) genes or gene sequences have.
Vorzugsweise können die erfindungsgemäßen Verbindungen in transgenen Kulturen eingesetzt werden, welche gegen Wuchsstoffe, wie z. B. Dicamba oder gegen Preferably, the compounds of the invention can be used in transgenic cultures which are resistant to growth factors, such as. B. Dicamba or against
Herbizide, die essentielle Pflanzenenzyme, z. B. Acetolactatsynthasen (ALS), EPSP Synthasen, Glutaminsynthasen (GS) oder Hydroxyphenylpyruvat Dioxygenasen (HPPD) hemmen, respektive gegen Herbizide aus der Gruppe der Sulfonylharnstoffe, der Glyphosate, Glufosinate oder Benzoylisoxazole und analogen Wirkstoffe, resistent sind.  Herbicides containing essential plant enzymes, e.g. As acetolactate synthases (ALS), EPSP synthases, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
Bei der Anwendung der erfindungsgemäßen Wirkstoffe in transgenen Kulturen treten neben den in anderen Kulturen zu beobachtenden Wirkungen gegenüber In the application of the active compounds according to the invention in transgenic cultures, in addition to the effects to be observed in other cultures
Schadpflanzen oftmals Wirkungen auf, die für die Applikation in der jeweiligen transgenen Kultur spezifisch sind, beispielsweise ein verändertes oder speziell erweitertes Unkrautspektrum, das bekämpft werden kann, veränderte Harmful plants often have effects that are specific for application in the particular transgenic culture, such as altered or specially extended weed spectrum that can be controlled
Aufwandmengen, die für die Applikation eingesetzt werden können, vorzugsweise gute Kombinierbarkeit mit den Herbiziden, gegenüber denen die transgene Kultur resistent ist, sowie Beeinflussung von Wuchs und Ertrag der transgenen Kulturpflanzen. Application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing growth and yield of the transgenic crops.
Gegenstand der Erfindung ist deshalb auch die Verwendung der erfindungsgemäßen Verbindungen als Herbizide zur Bekämpfung von Schadpflanzen in transgenen The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic
Kulturpflanzen. Die erfindungsgemäßen Verbindungen können in Form von Spritzpulvern, Crops. The compounds of the invention may be in the form of wettable powders,
emulgierbaren Konzentraten, versprühbaren Lösungen, Stäubemitteln oder Granulaten in den üblichen Zubereitungen angewendet werden. Gegenstand der Erfindung sind deshalb auch herbizide und pflanzenwachstumsregulierende Mittel, welche die erfindungsgemäßen Verbindungen enthalten. emulsifiable concentrates, sprayable solutions, dusts or granules are used in the usual preparations. The invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.
Die erfindungsgemäßen Verbindungen können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemisch-physikalischen Parameter vorgegeben sind. Als Formulierungsmöglichkeiten kommen beispielsweise in Frage: Spritzpulver (WP), wasserlösliche Pulver (SP), wasserlösliche Konzentrate, emulgierbare Konzentrate (EC), Emulsionen (EW), wie öl-in-Wasser- und Wasser-in-ÖI-Emulsionen, versprühbare Lösungen, Suspensionskonzentrate (SC), Dispersionen auf Öl- oder Wasserbasis, ölmischbare Lösungen, Kapselsuspensionen (CS), Stäubemittel (DP), Beizmittel, Granulate für die Streu- und Bodenapplikation, Granulate (GR) in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, wasserdispergierbare Granulate (WG), wasserlösliche Granulate (SG), The compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), Dusts (DP), mordants, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG),
ULV-Formulierungen, Mikrokapseln und Wachse. ULV formulations, microcapsules and waxes.
Diese einzelnen Formulierungstypen sind im Prinzip bekannt und werden  These individual formulation types are known and will be known in principle
beispielsweise beschrieben in: Winnacker-Küchler, "Chemische Technologie", for example, described in: Winnacker-Kuchler, "Chemical Technology",
Band 7, C. Hanser Verlag München, 4. Aufl. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973, K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London. Volume 7, C. Hanser Verlag Munich, 4th ed. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973, K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.
Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise The necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are, for example
beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid described in Watkins, Handbook of Insecticides Dust Diluents and Carriers, 2nd ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid
Chemistry", 2nd Ed., J. Wiley & Sons, N.Y., C. Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1963, McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J., Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964, Schönfeldt, "Grenzflächenaktive Chemistry, 2nd Ed., J. Wiley & Sons, NY, C. Marsden, "Solvents Guide", 2nd Ed., Interscience, NY 1963, McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ, Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964, Schonfeldt, "Surface Active
Äthylenoxidaddukte", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl. 1986. Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen Pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Herbiziden, Fungiziden, sowie mit Safenern, Düngemitteln und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmix. Geeignete Safener sind Äthylenoxidaddukte ", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler," Chemical Technology ", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986. On the basis of these formulations, combinations with other pesticide-active substances, such as insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and / or growth regulators, for example in the form of a ready-to-use formulation or as a tank mix
beispielsweise Mefenpyr-diethyl, Cyprosulfamid, Isoxadifen-ethyl, Cloquintocet-mexyl und Dichlormid. for example, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and dichloromide.
Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Tenside ionischer und/oder nichtionischer Art (Netzmittel, Dispergiermittel), z.B. polyoxyethylierte Alkylphenole, polyoxethylierte Fettalkohole, polyoxethylierte Fettamine, Fettalkoholpolyglykol- ethersulfate, Alkansulfonate, Alkylbenzolsulfonate, ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Zur Herstellung der Spritzpulver werden die herbiziden Wirkstoffe beispielsweise in üblichen Apparaturen wie Hammermühlen, Gebläsemühlen und Luftstrahlmühlen feingemahlen und gleichzeitig oder anschließend mit den Formulierungshilfsmitteln vermischt. Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance, also contain ionic and / or nonionic surfactants (wetting agents, dispersants) other than a diluent or inert substance, for example polyoxyethylated alkylphenols. polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ethersulfate, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalene-sulfonate, or sodium oleoylmethyltaurine. To prepare the wettable powders, the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem Emulsifiable concentrates are made by dissolving the active ingredient in one
organischen Lösungsmittel z.B. Butanol, Cyclohexanon, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen oder Mischungen der organischen Lösungsmittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calzium-Salze wie Ca-Dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid-Kondensationsprodukte, Alkylpolyether, Sorbitanester wie z.B. Sorbitanfettsäureester oder organic solvents e.g. Butanol, cyclohexanone, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers). Examples of emulsifiers which can be used are: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as e.g. Sorbitan fatty acid esters or
Polyoxethylensorbitanester wie z.B. Polyoxyethylensorbitanfettsäureester. Stäubemittel erhält man durch Vermählen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, oder Diatomeenerde. Polyoxethylenesorbitanester such. Polyoxyethylene. Dusts are obtained by milling the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspensionskonzentrate können auf Wasser- oder Ölbasis sein. Sie können beispielsweise durch Naß-Vermahlung mittels handelsüblicher Perlmühlen und gegebenenfalls Zusatz von Tensiden, wie sie z.B. oben bei den anderen Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. upstairs with the others
Formulierungstypen bereits aufgeführt sind, hergestellt werden. Formulation types already listed are produced.
Emulsionen, z.B. ÖI-in-Wasser-Emulsionen (EW), lassen sich beispielsweise mittels Rührern, Kolloidmühlen und/oder statischen Mischern unter Verwendung von wäßrigen organischen Lösungsmitteln und gegebenenfalls Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, herstellen. Emulsions, e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, as described e.g. listed above for the other formulation types.
Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaoiinite oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden. Granules can either be adsorbed by atomizing the active ingredient, granulated inert material or by applying active substance concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carriers such as sand, Kaoiinite or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
Wasserdispergierbare Granulate werden in der Regel nach den üblichen Verfahren wie Sprühtrocknung, Wirbelbett-Granulierung, Teller-Granulierung, Mischung mit Hochgeschwindigkeitsmischern und Extrusion ohne festes Inertmaterial hergestellt. Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
Zur Herstellung von Teller-, Fließbett-, Extruder- und Sprühgranulate siehe z.B. For the preparation of plate, fluid bed, extruder and spray granules, see e.g.
Verfahren in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London, J.E. Browning, "Agglomeration", Chemical and Engineering 1967, Seiten 147 ff, "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, S. 8-57. Method in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London, J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 et seq., "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.
Für weitere Einzelheiten zur Formulierung von Pflanzenschutzmitteln siehe z.B. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961 , Seiten 81 -96 und J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, Seiten 101-103. For further details on the formulation of crop protection agents see, e.g. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96 and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.
Die agrochemischen Zubereitungen enthalten in der Regel 0.1 bis 99 Gew.-%, insbesondere 0.1 bis 95 Gew.-%, erfindungsgemäße Verbindungen. The agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
In Spritzpulvern beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei  In wettable powders, the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients. at
emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 1 bis 90, emulsifiable concentrates, the active substance concentration can be about 1 to 90,
vorzugsweise 5 bis 80 Gew.-% betragen. Staubförmige Formulierungen enthalten 1 bis 30 Gew.-% Wirkstoff, vorzugsweise meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen enthalten etwa 0.05 bis 80, vorzugsweise 2 bis 50 Gew.-% Wirkstoff. Bei wasserdispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche preferably 5 to 80 wt .-% amount. Dust-like formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% active ingredient. In the case of water-dispersible granules, the active ingredient content depends, in part, on whether the active compound is liquid or solid and which
Granulierhilfsmittel, Füllstoffe usw. verwendet werden. Bei den in Wasser Granulation aids, fillers, etc. are used. In the water
dispergierbaren Granulaten liegt der Gehalt an Wirkstoff beispielsweise zwischen 1 und 95 Gew.-%, vorzugsweise zwischen 10 und 80 Gew.-%. Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Konservierungs-, dispersible granules, the content of active ingredient is for example between 1 and 95 wt .-%, preferably between 10 and 80 wt .-%. In addition, the active substance formulations mentioned optionally contain the customary adhesive, wetting, dispersing, emulsifying, penetrating, preserving,
Frostschutz- und Lösungsmittel, Füll-, Träger- und Farbstoffe, Entschäumer, Antifreeze and solvents, fillers, carriers and dyes, defoamers,
Verdunstungshemmer und den pH -Wert und die Viskosität beeinflussende Mittel. Evaporation inhibitor and the pH and viscosity affecting agents.
Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen Pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Herbiziden, Fungiziden, sowie mit Safenern, Düngemitteln und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmix. On the basis of these formulations, combinations with other pesticidally active substances, such as e.g. Insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a ready-made formulation or as a tank mix.
Zur Anwendung werden die in handelsüblicher Form vorliegenden Formulierungen gegebenenfalls in üblicher Weise verdünnt z.B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Boden- bzw. Streugranulate sowie versprühbare For use, the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dusty preparations, ground or spreading granules and sprayable
Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt.  Solutions are usually no longer diluted with other inert substances before use.
Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit, der Art des verwendeten Herbizids, u.a. variiert die erforderliche Aufwandmenge der Verbindungen der Formel (I). Sie kann innerhalb weiter Grenzen schwanken, z.B. zwischen 0,001 und 1 ,0 kg/ha oder mehr Aktivsubstanz, vorzugsweise liegt sie jedoch zwischen 0,005 und 750 g/ha. With the external conditions such as temperature, humidity, the type of herbicide used, u.a. varies the required application rate of the compounds of formula (I). It can vary within wide limits, e.g. between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 0.005 and 750 g / ha.
Die nachstehenden Beispiele erläutern die Erfindung. The following examples illustrate the invention.
A. Chemische Beispiele A. Chemical examples
Synthese von 7-Methyl-N-(1 -methyl-1 H-tetrazol-5-yl)-1 -benzothiophen-6-carboxamid (Beispiel Nr. 1 -1 )  Synthesis of 7-methyl-N- (1-methyl-1H-tetrazol-5-yl) -1-benzothiophene-6-carboxamide (Example No. 1 -1)
Schritt 1 : Synthese von 7-Methyl-1 -benzothiophen-6-carbonsäuremethylester  Step 1: Synthesis of 7-methyl-1-benzothiophene-6-carboxylic acid methyl ester
Die Synthese von 3-Hydroxy-7-methyl-2,3-dihydro-1-benzothiophen-6-carbonsäure- methylester ist bekannt und beispielsweise in DE 19532312 (Beispiel 16) beschrieben. 619 mg (3 mmol) para-Toluolsulfonsäure wurden zu einer Lösung von 7.3 g (32 mmol) 3-Hydroxy-7-methyl-2,3-dihydro-1 -benzothiophen-6-carbonsäuremethylester in 92 ml Toluol gegeben. Die Mischung wurde 1 h lang unter Rückfluss erhitzt. Anschließend wurde das Gemisch auf Raumtemperatur (RT) abgekühlt und mit 60 ml einer gesättigten wässrigen Natriumhydrogencarbonatlösung gewaschen. Nach der The synthesis of methyl 3-hydroxy-7-methyl-2,3-dihydro-1-benzothiophene-6-carboxylate is known and described, for example, in DE 19532312 (Example 16). 619 mg (3 mmol) of para-toluenesulfonic acid were added to a solution of 7.3 g (32 mmol) of methyl 3-hydroxy-7-methyl-2,3-dihydro-1-benzothiophene-6-carboxylate in 92 ml of toluene. The mixture was refluxed for 1 h. Subsequently The mixture was cooled to room temperature (RT) and washed with 60 ml of a saturated aqueous sodium bicarbonate solution. After
Phasentrennung wurde die organische Phase getrocknet und das Filtrat wurde vom Lösungsmittel befreit. Es wurden 6.0 g des gewünschten Produkts erhalten. Phase separation, the organic phase was dried and the filtrate was freed from the solvent. There were obtained 6.0 g of the desired product.
Schritt 2: Synthese von 7-Methyl-1 -benzothiophen-6-carbonsäure Step 2: Synthesis of 7-methyl-1-benzothiophene-6-carboxylic acid
Eine Lösung von 6.0 g (28 mmol) 7-Methyl-1 -benzothiophen-6-carbonsäuremethyl- ester in einem Gemisch aus 50 ml Methanol und 10 ml Wasser wurde mit 1 .73 g (43 mmol) Natriumhydroxid versetzt. Die Reaktionsmischung wurde 1 h lang unter Rückfluss erhitzt. Anschließend wurde das Methanol weitgehend entfernt und derA solution of 6.0 g (28 mmol) of methyl 7-methyl-1-benzothiophene-6-carboxylate in a mixture of 50 ml of methanol and 10 ml of water was treated with 1.73 g (43 mmol) of sodium hydroxide. The reaction mixture was heated at reflux for 1 h. Subsequently, the methanol was largely removed and the
Rückstand wurde in 10 ml Wasser aufgenommen. Das Gemisch wurde zweimal mit je 10 ml Diethylether gewaschen. Danach wurde die wässrige Phase mit 2M Salzsäure angesäuert. Die entstandene Suspension wurde filtriert und der isolierte Feststoff wurde mit 20 ml Wasser gewaschen und schließlich getrocknet. Es wurden 4.1 g des gewünschten Produkts gewonnen. The residue was taken up in 10 ml of water. The mixture was washed twice with 10 ml each of diethyl ether. Thereafter, the aqueous phase was acidified with 2M hydrochloric acid. The resulting suspension was filtered and the isolated solid was washed with 20 ml of water and finally dried. 4.1 g of the desired product were obtained.
Schritt 3: Synthese von 7-Methyl-N-(1-methyl-1 H-tetrazol-5-yl)-1-benzothiophen-6- carboxamid Step 3: Synthesis of 7-methyl-N- (1-methyl-1H-tetrazol-5-yl) -1-benzothiophene-6-carboxamide
500 mg (2.60 mmol) 7-Methyl-1 -benzothiophen-6-carbonsäure und 335 mg (98% Reinheit; 3.31 mmol) 5-Amino-1-methyl-1 H-tetrazol wurden in 10 ml trockenem Pyridin auf eine Temperatur von 0 °C - 5 °C abgekühlt. Anschließend wurden 462 mg (3.64 mmol) Oxalsäuredichlorid zugegeben. Das Gemisch wurde auf RT aufgetaut und danach noch 2 h bei RT gerührt. Anschließend wurden bei RT weitere 1 15.5 mg (0.91 mmol) Oxalsäuredichlorid zugegeben. Die Reaktionsmischung wurde 16 h bei RT gerührt. Zur Aufarbeitung wurde das Lösungsmittel entfernt. Der Rückstand wurde in Dichlormethan aufgenommen und das Gemisch wurde mit gesättigter wässriger Natriumhydrogencarbonatlösung gewaschen. Nach der Phasentrennung wurde die organische Phase vom Lösungsmittel befreit. Der Rückstand wurde mit Acetonitril verrührt und filtriert. Als Rückstand wurden 355 mg sauberes Produkt gewonnen.  500 mg (2.60 mmol) of 7-methyl-1-benzothiophene-6-carboxylic acid and 335 mg (98% purity; 3.31 mmol) of 5-amino-1-methyl-1H-tetrazole were dissolved in 10 ml of dry pyridine to a temperature of 0 ° C - 5 ° C cooled. Subsequently, 462 mg (3.64 mmol) of oxalic acid dichloride were added. The mixture was thawed to RT and then stirred for 2 h at RT. Subsequently, another 1 15.5 mg (0.91 mmol) of oxalic acid dichloride was added at RT. The reaction mixture was stirred at RT for 16 h. For workup, the solvent was removed. The residue was taken up in dichloromethane and the mixture was washed with saturated aqueous sodium bicarbonate solution. After phase separation, the organic phase was freed from the solvent. The residue was triturated with acetonitrile and filtered. The residue obtained was 355 mg of clean product.
Die in den nachfolgenden Tabellen aufgeführten Beispiele wurden analog oben genannten Methoden hergestellt beziehungsweise sind analog oben genannten Methoden erhältlich. Die in den nachfolgenden Tabellen aufgeführten Verbindungen sind ganz besonders bevorzugt. ie verwendeten Abkürzungen entsprechen den allgemein bekannten und bedeuten: The examples listed in the following tables were prepared analogously to the above-mentioned methods or are obtainable analogously to the abovementioned methods. The compounds listed in the tables below are very particularly preferred. The abbreviations used correspond to the generally known and mean:
Et = Ethyl Me = Methyl n-Pr = n-Propyl c-Pr = c-Propyl c = cyclo t = tertiär t-Bu = t-Butyl Ph = Phenyl Et = ethyl Me = methyl n-Pr = n-propyl c-Pr = c-propyl c = cyclo t = tertiary t-Bu = t-butyl Ph = phenyl
Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , R* für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A30 bedeutet, worin die Reste R7 und R8 beide für Wasserstoff stehen Compounds of the invention of the general formula (I) wherein Q is Q1, R * is a methyl group and R is hydrogen and L is the bridge A30, wherein the radicals R 7 and R 8 are both hydrogen
Tabelle 2: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine Ethylgruppe und R für Wasserstoff stehen und L die Brücke A30 bedeutet, worin die Reste R7 und R8 beide für Wasserstoff stehen Table 2: Compounds of the invention of the general formula (I) wherein Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A30, wherein the radicals R 7 and R 8 are both hydrogen
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
2-1 Me H  2-1 Me H
2-2 Et H  2-2 Et H
2-3 Cl H  2-3 Cl H
2-4 OMe H  2-4 OMe H
2-5 CF3 H 2-5 CF 3 H
2-6 S02 e H 2-6 S0 2 e H
2-7 CH2OMe H 2-7 CH 2 OMe H
2-8 CH20(CH2)2OMe H 2-8 CH 2 O (CH 2 ) 2 OMe H
2-9 Me Me  2-9 Me Me
2-10 Et Me  2-10 Et Me
2-1 1 Cl Me  2-1 1 Cl Me
2-12 OMe Me  2-12 OMe Me
2-13 CF3 Me 2-13 CF 3 Me
2-14 S02Me Me 2-14 S0 2 Me Me
2-15 CH2OMe Me 2-15 CH 2 OMe Me
2-16 CH20(CH2)2OMe Me Tabelle 3: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine n-Propylgruppe und R für Wasserstoff stehen und L die Brücke A30 bedeutet, worin die Reste R7 und R8 beide für Wasserstoff stehen 2-16 CH 2 O (CH 2 ) 2 OMe Me Table 3: Compounds of the invention of the general formula (I) wherein Q is Q1, R x is an n-propyl group and R is hydrogen and L is the bridge A30, in which the radicals R 7 and R 8 are both hydrogen
Tabelle 4: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2, Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A30 bedeutet, worin die Reste R7 und R8 beide für Wasserstoff stehen Table 4: Compounds of the invention of the general formula (I) wherein Q is Q 2, R x is a methyl group and R is hydrogen and L is the bridge A30, wherein the radicals R 7 and R 8 are both hydrogen
Tabelle 5: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q3, RY für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A30 bedeutet, worin die Reste R7 und R8 beide für Wasserstoff stehen Table 5: Compounds of the invention of the general formula (I) in which Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A30, in which the radicals R 7 and R 8 are both hydrogen
Tabelle 6: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q4, Rz für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A30 bedeutet, worin die Reste R7 und R8 beide für Wasserstoff stehen Table 6: Compounds of the invention of the general formula (I) wherein Q is Q4, R stand for a methyl group and R is hydrogen and L the bridge A30 is wherein the radicals R 7 and R 8 are both hydrogen
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
6-1 Me H  6-1 Me H
6-2 Et H  6-2 Et H
6-3 Cl H  6-3 Cl H
6-4 OMe H  6-4 OMe H
6-5 CF3 H 6-5 CF 3 H
6-6 S02Me H 6-6 S0 2 Me H
6-7 Ch OMe H  6-7 Ch OMe H
6-8 CH20(CH2)2OMe H 6-8 CH 2 O (CH 2 ) 2 OMe H
6-9 Me Me  6-9 Me Me
6-10 Et Me  6-10 Et Me
6-1 1 Cl Me  6-1 1 Cl Me
6-12 OMe Me  6-12 OMe Me
6-13 CF3 Me 6-13 CF 3 Me
6-14 S02Me Me 6-14 S0 2 Me Me
6-15 CH2OMe Me 6-15 CH 2 OMe Me
6-16 CH20(CH2)2OMe Me Tabelle 7: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A32 bedeutet, worin die Reste R7 und R8 beide für Wasserstoff stehen 6-16 CH 2 O (CH 2 ) 2 OMe Me Table 7: Compounds of the invention of the general formula (I) wherein Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A32, wherein the radicals R 7 and R 8 are both hydrogen
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
7-1 Me H (400 MHz. DMSO-de δ, ppm) 7.94 (d,1 H), 7.68 (d,1 H), 7.57  7-1 Me H (400 MHz, DMSO-de δ, ppm) 7.94 (d, 1H), 7.68 (d, 1H), 7.57
(d,1 H), 7.50 (d,1 H), 3.99 (s,3H), 2.63 (s,3H)  (d, 1H), 7.50 (d, 1H), 3.99 (s, 3H), 2.63 (s, 3H)
7-2 Et H  7-2 Et H
7-3 Cl H  7-3 Cl H
7-4 OMe H  7-4 OMe H
7-5 CF3 H 7-5 CF 3 H
7-6 S02Me H 7-6 S0 2 Me H
7-7 CH2OMe H 7-7 CH 2 OMe H
7-8 CH20(CH2)2OMe H 7-8 CH 2 0 (CH 2 ) 2 OMe H
7-9 Me Me  7-9 Me Me
7-10 Et Me  7-10 et me
7-1 1 Cl Me  7-1 1 Cl Me
7-12 OMe Me  7-12 OMe Me
7-13 CF3 Me 7-13 CF 3 Me
7-14 S02Me Me 7-14 S0 2 Me Me
7-15 CH2OMe Me 7-15 CH 2 OMe Me
7-16 CH20(CH2)2OMe Me Tabelle 8: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine Ethylgruppe und R für Wasserstoff stehen und L die Brücke A32 bedeutet, worin die Reste R7 und R8 beide für Wasserstoff stehen 7-16 CH 2 O (CH 2 ) 2 OMe Me Table 8: Compounds of the invention of the general formula (I) wherein Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A32, wherein the radicals R 7 and R 8 are both hydrogen
Tabelle 9: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine n-Propylgruppe und R für Wasserstoff stehen und L die Brücke A32 bedeutet, worin die Reste R7 und R8 beide für Wasserstoff stehen Table 9: Compounds of the invention of the general formula (I) wherein Q is Q1, R x is an n-propyl group and R is hydrogen and L is the bridge A32, wherein the radicals R 7 and R 8 are both hydrogen
Tabelle 10: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2, Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A32 bedeutet, worin die Reste R7 und R8 beide für Wasserstoff stehen Table 10: Compounds of the invention of the general formula (I) wherein Q is Q 2, R x is a methyl group and R is hydrogen and L is the bridge A32, wherein the radicals R 7 and R 8 are both hydrogen
Tabelle 1 1 : Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q3, RY für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A32 bedeutet, worin die Reste R7 und R8 beide für Wasserstoff stehen Table 1 1: Compounds of the invention of the general formula (I), wherein Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A32, wherein the radicals R 7 and R 8 are both hydrogen
Tabelle 12: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q4, Rz für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A32 bedeutet, worin die Reste R7 und R8 beide für Wasserstoff stehen Compounds of the invention of the general formula (I) wherein Q is Q4, R stand for a methyl group and R is hydrogen and L the bridge A32 is wherein the radicals R 7 and R 8 are both hydrogen: Table 12
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
12-1 Me H  12-1 Me H
12-2 Et H  12-2 Et H
12-3 Cl H  12-3 Cl H
12-4 OMe H  12-4 OMe H
12-5 CF3 H 12-5 CF 3 H
12-6 S02Me H 12-6 S0 2 Me H
12-7 CH2OMe H 12-7 CH 2 OMe H
12-8 CH20(CH2)2OMe H 12-8 CH 2 0 (CH 2 ) 2 OMe H
12-9 Me Me  12-9 Me Me
12-10 Et Me  12-10 et me
12-1 1 Cl Me  12-1 1 Cl Me
12-12 OMe Me  12-12 OMe Me
12-13 CF3 Me 12-13 CF 3 Me
12-14 S02Me Me 12-14 S0 2 Me Me
12-15 CH2OMe Me 12-15 CH 2 OMe Me
12-16 CH20(CH2)2OMe Me Tabelle 13: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A8 bedeutet, worin der Rest R7 für Wasserstoff steht 12-16 CH 2 O (CH 2 ) 2 OMe Me Table 13: Compounds of the invention of the general formula (I) wherein Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A8, wherein the radical R 7 is hydrogen
Nr. X W R8 Physikalische Daten (1H-NMR) No. XWR 8 Physical Data ( 1 H-NMR)
13-1 Me H H  13-1 Me H H
13-2 Et H H  13-2 Et H H
13-3 Gl H H  13-3 HH
13-4 OMe H H  13-4 OMe H H
13-5 CF3 H H 13-5 CF 3 HH
13-6 S02Me H H 13-6 S0 2 Me HH
13-7 CH2OMe H H 13-7 CH 2 OMe HH
13-8 CH20(CH2)2OMe H H 13-8 CH 2 0 (CH 2 ) 2 OMe HH
13-9 Me Me H  13-9 Me Me H
13-10 Et Me H  13-10 Et Me H
13-1 1 Gl Me H  13-1 1 Gl Me H
13-12 OMe Me H  13-12 OMe Me H
13-13 CF3 Me H 13-13 CF 3 Me H
13-14 S02Me Me H 13-14 S0 2 Me Me H
13-15 CH2OMe Me H 13-15 CH 2 OMe Me H
13-16 CH20(CH2)2OMe Me H 13-16 CH 2 0 (CH 2 ) 2 OMe Me H
13-17 Me H Me  13-17 Me H Me
13-18 Et H Me  13-18 Et H Me
13-19 Gl H Me  13-19 Gl H Me
13-20 OMe H Me  13-20 OMe H Me
13-21 CF3 H Me 13-21 CF 3 H Me
13-22 S02Me H Me 13-22 S0 2 Me H Me
13-23 CH2OMe H Me 13-23 CH 2 OMe H Me
13-24 CH20(CH2)2OMe H Me 13-24 CH 2 O (CH 2 ) 2 OMe H Me
13-25 Me Me Me  13-25 Me Me Me
13-26 Et Me Me Nr. X W R8 Physikalische Daten (Ή-NMR)13-26 Et Me Me No. XWR 8 Physical Data (Ή-NMR)
13-27 Cl Me Me 13-27 Cl Me Me
13-28 OMe Me Me  13-28 OMe Me Me
13-29 CF3 Me Me 13-29 CF 3 Me Me
13-30 S02Me Me Me 13-30 S0 2 Me Me Me
13-31 CH2OMe Me Me 13-31 CH 2 OMe Me Me
13-32 CH20(CH2)20Me Me Me 13-32 CH 2 O (CH 2 ) 20 Me Me
Tabelle 14: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Table 14: Compounds of the invention of the general formula (I) in which Q is
Q1 , Rx für eine Ethylgruppe und R für Wasserstoff stehen und L die Brücke A8 bedeutet, worin der Rest R7 für Wasserstoff steht Q1, R x is an ethyl group and R is hydrogen and L is the bridge A8, wherein the radical R 7 is hydrogen
Nr. X W R8 Physikalische Daten (Ή-NMR) No. XWR 8 Physical Data (Ή-NMR)
14-1 Me H H  14-1 Me H H
14-2 Et H H  14-2 Et H H
14-3 Cl H H  14-3 Cl H H
14-4 OMe H H  14-4 OMe H H
14-5 CF3 H H 14-5 CF 3 HH
14-6 S02Me H H 14-6 S0 2 Me HH
14-7 CH2OMe H H 14-7 CH 2 OMe HH
14-8 CH20(CH2)2OMe H H 14-8 CH 2 0 (CH 2 ) 2 OMe HH
14-9 Me Me H  14-9 Me Me H
14-10 Et Me H  14-10 Et Me H
14-1 1 Cl Me H  14-1 1 Cl Me H
14-12 OMe Me H  14-12 OMe Me H
14-13 CF3 Me H 14-13 CF 3 Me H
14-14 S02Me Me H 14-14 S0 2 Me Me H
14-15 CH2OMe Me H Nr. X W R8 Physikalische Daten (Ή-NMR) 14-15 CH 2 OMe Me H No. XWR 8 Physical Data (Ή-NMR)
14-16 CH20(CH2)2OMe Me H 14-16 CH 2 0 (CH 2 ) 2 OMe Me H
14-17 Me H Me  14-17 Me H Me
14-18 Et H Me  14-18 Et H Me
14-19 Cl H Me  14-19 Cl H Me
14-20 OMe H Me  14-20 OMe H Me
14-21 CF3 H Me 14-21 CF 3 H Me
14-22 S02Me H Me 14-22 S0 2 Me H Me
14-23 CH2OMe H Me 14-23 CH 2 OMe H Me
14-24 CH20(CH2)2OMe H Me 14-24 CH 2 0 (CH 2 ) 2 OMe H Me
14-25 Me Me Me  14-25 Me Me Me
14-26 Et Me Me  14-26 Et Me Me
14-27 Cl Me Me  14-27 Cl Me Me
14-28 OMe Me Me  14-28 OMe Me Me
14-29 CF3 Me Me 14-29 CF 3 Me Me
14-30 S02Me Me Me 14-30 S0 2 Me Me Me
14-31 CH2OMe Me Me 14-31 CH 2 OMe Me Me
14-32 CH20(CH2)2OMe Me Me 14-32 CH 2 O (CH 2 ) 2 OMe Me Me
Tabelle 15: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Table 15: Compounds of the invention of the general formula (I) wherein Q is
Q1 , Rx für eine n-Propylgruppe und R für Wasserstoff stehen und L die Brücke A8 bedeutet, worin der Rest R7 für Wasserstoff steht Q1, R x and stand for a n-propyl group and R is hydrogen L represents the bridge A8, where R 7 is hydrogen
Nr. X W R8 Physikalische Daten (Ή-NMR) No. XWR 8 Physical Data (Ή-NMR)
15-1 Me H H  15-1 Me H H
15-2 Et H H  15-2 Et H H
15-3 Cl H H  15-3 Cl H H
15-4 OMe H H  15-4 OMe H H
15-5 CF.3 H H Nr. X W R8 Physikalische Daten (Ή-NMR)15-5 CF.3 HH No. XWR 8 Physical Data (Ή-NMR)
15-6 S02Me H H 15-6 S0 2 Me HH
15-7 CH2OMe H H 15-7 CH 2 OMe HH
15-8 CH20(CH2)2OMe H H 15-8 CH 2 0 (CH 2 ) 2 OMe HH
15-9 Me Me H  15-9 Me Me H
15-10 Et Me H  15-10 Et Me H
15-1 1 Gl Me H  15-1 1 Gl Me H
15-12 OMe Me H  15-12 OMe Me H
15-13 CF3 Me H 15-13 CF 3 Me H
15-14 S02Me Me H 15-14 S0 2 Me Me H
15-15 CH2OMe Me H 15-15 CH 2 OMe Me H
15-16 CH20(CH2)2OMe Me H 15-16 CH 2 O (CH 2 ) 2 OMe Me H
15-17 Me H Me  15-17 Me H Me
15-18 Et H Me  15-18 Et H Me
15-19 Gl H Me  15-19 HH Me
15-20 OMe H Me  15-20 OMe H Me
15-21 CF3 H Me 15-21 CF 3 H Me
15-22 S02Me H Me 15-22 S0 2 Me H Me
15-23 CH2OMe H Me 15-23 CH 2 OMe H Me
15-24 CH20(CH2)2OMe H Me 15-24 CH 2 O (CH 2 ) 2 OMe H Me
15-25 Me Me Me  15-25 Me Me Me
15-26 Et Me Me  15-26 Et Me Me
15-27 Gl Me Me  15-27 Gl Me Me
15-28 OMe Me Me  15-28 OMe Me Me
15-29 CF3 Me Me 15-29 CF 3 Me Me
15-30 S02Me Me Me 15-30 S0 2 Me Me Me
15-31 CH2OMe Me Me 15-31 CH 2 OMe Me Me
15-32 CH20(CH2)2OMe Me Me Tabelle 16: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2, Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A8 bedeutet, worin der Rest R7 für Wasserstoff steht 15-32 CH 2 O (CH 2 ) 2 OMe Me Me Table 16: Compounds of the invention of the general formula (I) wherein Q is Q 2, R x is a methyl group and R is hydrogen and L is the bridge A8 in which the radical R 7 is hydrogen
Nr. X W R8 Physikalische Daten (Ή-NMR) No. XWR 8 Physical Data (Ή-NMR)
16-26 Et Me Me 16-26 Et Me Me
16-27 Cl Me Me  16-27 Cl Me Me
16-28 OMe Me Me  16-28 OMe Me Me
16-29 CF3 Me Me 16-29 CF 3 Me Me
16-30 S02Me Me Me 16-30 S0 2 Me Me Me
16-31 Ch OMe Me Me  16-31 Ch OMe Me Me
16-32 CH20(CH2)2OMe Me Me 16-32 CH 2 O (CH 2 ) 2 OMe Me Me
Tabelle 17: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Table 17: Compounds of the invention of the general formula (I) in which Q is
Q3, RY für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A8 bedeutet, worin der Rest R7 für Wasserstoff steht Q3, R Y is a methyl group and R is hydrogen and L is the bridge A8, wherein the radical R 7 is hydrogen
Nr. X W R8 Physikalische Daten (Ή-NMR) No. XWR 8 Physical Data (Ή-NMR)
17-1 Me H H  17-1 Me H H
17-2 Et H H  17-2 Et H H
17-3 Cl H H  17-3 Cl H H
17-4 OMe H H  17-4 OMe H H
17-5 CF3 H H 17-5 CF 3 HH
17-6 S02Me H H 17-6 S0 2 Me HH
17-7 CH2OMe H H 17-7 CH 2 OMe HH
17-8 CH20(CH2)2OMe H H 17-8 CH 2 0 (CH 2 ) 2 OMe HH
17-9 Me Me H  17-9 Me Me H
17-10 Et Me H  17-10 Et Me H
17-1 1 Cl Me H  17-1 1 Cl Me H
17-12 OMe Me H  17-12 OMe Me H
17-13 CF3 Me H 17-13 CF 3 Me H
17-14 S02Me Me H 17-14 S0 2 Me Me H
17-15 CH2OMe Me H 17-15 CH 2 OMe Me H
17-16 CH20(CH2)2OMe Me H Nr. X W R8 Physikalische Daten (Ή-NMR)17-16 CH 2 0 (CH 2 ) 2 OMe Me H No. XWR 8 Physical Data (Ή-NMR)
17-17 Me H Me 17-17 Me H Me
17-18 Et H Me  17-18 Et H Me
17-19 Cl H Me (400 MHz. DMSO-de ö, ppm) 8.08 (d,1 H), 7.90  17-19 Cl H Me (400 MHz, DMSO-de ö, ppm) 8.08 (d, 1 H), 7.90
(d,1 H), 7.50 (s, 1 H), 2.40 (s,3H), 2.23 (s,3H)  (d, 1H), 7.50 (s, 1H), 2.40 (s, 3H), 2.23 (s, 3H)
17-20 OMe H Me  17-20 OMe H Me
17-21 CF3 H Me 17-21 CF 3 H Me
17-22 S02Me H Me 17-22 S0 2 Me H Me
17-23 CH2OMe H Me 17-23 CH 2 OMe H Me
17-24 CH20(CH2)2OMe H Me 17-24 CH 2 0 (CH 2 ) 2 OMe H Me
17-25 Me Me Me  17-25 Me Me Me
17-26 Et Me Me  17-26 Et Me Me
17-27 Cl Me Me  17-27 Cl Me Me
17-28 OMe Me Me  17-28 OMe Me Me
17-29 CF3 Me Me 17-29 CF 3 Me Me
17-30 S02Me Me Me 17-30 S0 2 Me Me Me
17-31 CH2OMe Me Me 17-31 CH 2 OMe Me Me
17-32 CH20(CH2)2OMe Me Me 17-32 CH 2 O (CH 2 ) 2 OMe Me Me
Tabelle 18: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Table 18: Compounds of the invention of the general formula (I) wherein Q is
Q4, Rz für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A8 bedeutet, worin der Rest R7 für Wasserstoff steht Q4, R z represent a methyl group and R is hydrogen and L is the bridge A8, where R 7 is hydrogen
Nr. X W R8 Physikalische Daten (Ή-NMR) No. X W R8 Physical Data (Ή-NMR)
18-1 Me H H  18-1 Me H H
18-2 Et H H  18-2 Et H H
18-3 Cl H H  18-3 Cl H H
18-4 OMe H H  18-4 OMe H H
18-5 CF3 H H Tabelle 19: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A363 bedeutet, worin die Reste R28,R29, R30 und R31 für 18-5 CF 3 HH Table 19: Compounds of the invention of the general formula (I), wherein Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A363, wherein the radicals R 28 , R 29 , R 30 and R 31 is
Wasserstoff stehen  Hydrogen stand
Tabelle 20: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine Ethylgruppe und R für Wasserstoff stehen und L die Brücke A363 bedeutet, worin die Reste R28,R29, R30 und R31 für Table 20: Compounds of the invention of the general formula (I) wherein Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A363, wherein the radicals R 28 , R 29 , R 30 and R 31 is
Wasserstoff stehen  Hydrogen stand
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
20-1 Me H  20-1 Me H
20-2 Et H  20-2 Et H
20-3 Cl H  20-3 Cl H
20-4 OMe H  20-4 OMe H
20-5 CF3 H 20-5 CF 3 H
20-6 S02Me H 20-6 S0 2 Me H
20-7 CH2OMe H 20-7 CH 2 OMe H
20-8 CH20(CH2)2OMe H 20-8 CH 2 O (CH 2 ) 2 OMe H
20-9 Me Me  20-9 Me Me
20-10 Et Me  20-10 et me
20-1 1 Cl Me  20-1 1 Cl Me
20-12 OMe Me  20-12 OMe Me
20-13 CF3 Me 20-13 CF 3 Me
20-14 S02Me Me 20-14 S0 2 Me Me
20-15 CH2OMe Me 20-15 CH 2 OMe Me
20-16 CH20(CH2)2OMe Me Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine n-Propylgruppe und R für Wasserstoff stehen und L die Brücke A363 bedeutet, worin die Reste R28,R29, R30 und R31 für Wasserstoff stehen 20-16 CH 2 O (CH 2 ) 2 OMe Me Compounds of the invention of the general formula (I) wherein Q is Q1, R x is an n-propyl group and R is hydrogen and L is the bridge A363, wherein the radicals R 28 , R 29 , R 30 and R 31 are hydrogen
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
21-1 Me H  21-1 Me H
21-2 Et H  21-2 Et H
21-3 Cl H  21-3 Cl H
21-4 OMe H  21-4 OMe H
21-5 CF3 H 21-5 CF 3 H
21-6 S02Me H 21-6 S0 2 Me H
21-7 CH2OMe H 21-7 CH 2 OMe H
21-8 CH20(CH2)2OMe H 21-8 CH 2 0 (CH 2 ) 2 OMe H
21-9 Me Me  21-9 Me Me
21-10 Et Me  21-10 et me
21-1 1 Cl Me  21-1 1 Cl Me
21-12 OMe Me  21-12 OMe Me
21-13 CF3 Me 21-13 CF 3 Me
21-14 S02Me Me 21-14 S0 2 Me Me
21-15 CH2OMe Me 21-15 CH 2 OMe Me
21-16 CH20(CH2)2OMe Me Tabelle 22: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2, Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A363 bedeutet, worin die Reste R28,R29, R30 und R31 für 21-16 CH 2 O (CH 2 ) 2 OMe Me Table 22: Compounds of the invention of the general formula (I) wherein Q is Q 2, R x is a methyl group and R is hydrogen and L is the bridge A363, wherein the radicals R 28 , R 29 , R 30 and R 31 is
Wasserstoff stehen  Hydrogen stand
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
22-1 Me H  22-1 Me H
22-2 Et H  22-2 Et H
22-3 Cl H  22-3 Cl H
22-4 OMe H  22-4 OMe H
22-5 CF3 H 22-5 CF 3 H
22-6 S02Me H 22-6 S0 2 Me H
22-7 CH2OMe H 22-7 CH 2 OMe H
22-8 CH20(CH2)2OMe H 22-8 CH 2 0 (CH 2 ) 2 OMe H
22-9 Me Me  22-9 Me Me
22-10 Et Me  22-10 Et Me
22-1 1 Cl Me  22-1 1 Cl Me
22-12 OMe Me  22-12 OMe Me
22-13 CF3 Me 22-13 CF 3 Me
22-14 S02Me Me 22-14 S0 2 Me Me
22-15 CH2OMe Me 22-15 CH 2 OMe Me
22-16 CH20(CH2)2OMe Me Tabelle 23: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q3, RY für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A363 bedeutet, worin die Reste R28,R29, R30 und R31 für 22-16 CH 2 O (CH 2 ) 2 OMe Me Table 23: Compounds of the invention of the general formula (I) wherein Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A363, wherein the radicals R 28 , R 29 , R 30 and R 31 are
Wasserstoff stehen  Hydrogen stand
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
23-1 Me H  23-1 Me H
23-2 Et H  23-2 Et H
23-3 Gl H  23-3 H
23-4 OMe H  23-4 OMe H
23-5 CF3 H 23-5 CF 3 H
23-6 S02Me H 23-6 S0 2 Me H
23-7 CH2OMe H 23-7 CH 2 OMe H
23-8 CH20(CH2)2OMe H 23-8 CH 2 0 (CH 2 ) 2 OMe H
23-9 Me Me  23-9 Me Me
23-10 Et Me  23-10 Et Me
23-1 1 Gl Me  23-1 1 Gl Me
23-12 OMe Me  23-12 OMe Me
23-13 CF3 Me 23-13 CF 3 Me
23-14 S02Me Me 23-14 S0 2 Me Me
23-15 CH2OMe Me 23-15 CH 2 OMe Me
23-16 CH20(CH2)2OMe Me Tabelle 24: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q4, Rz für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A363 bedeutet, worin die Reste R28,R29, R30 und R31 für 23-16 CH 2 O (CH 2 ) 2 OMe Me Table 24: Compounds of the invention of the general formula (I) wherein Q is Q4, R stand for a methyl group and R is hydrogen and L the bridge A363 means, in which the radicals R 28, R 29, R 30 and R 31 for
Wasserstoff stehen  Hydrogen stand
Tabelle 25: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A364 bedeutet, worin die Reste R29, R 30 und R31 für Wasserstoff stehen Table 25: Compounds according to the invention of the general formula (I) in which Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A364 in which R 29 , R 30 and R 31 are hydrogen
Tabelle 26: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine Ethylgruppe und R für Wasserstoff stehen und L die Brücke A364 bedeutet, worin die Reste R29, R 30 und R31 für Wasserstoff stehen Table 26: Compounds according to the invention of the general formula (I) in which Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A364 in which the radicals R 29 , R 30 and R 31 are hydrogen
Nr. X W Physikalische Daten (1H-NMR) No. XW Physical Data ( 1 H-NMR)
26-1 Me H  26-1 Me H
26-2 Et H  26-2 Et H
26-3 Gl H  26-3 Eq H
26-4 OMe H  26-4 OMe H
26-5 CF3 H 26-5 CF 3 H
26-6 S02Me H 26-6 S0 2 Me H
26-7 Ch OMe H  26-7 Ch OMe H
26-8 CH20(CH2)2OMe H 26-8 CH 2 0 (CH 2 ) 2 OMe H
26-9 Me Me  26-9 Me Me
26-10 Et Me  26-10 et me
26-1 1 Gl Me  26-1 1 Gl Me
26-12 OMe Me  26-12 OMe Me
26-13 CF3 Me 26-13 CF 3 Me
26-14 S02Me Me 26-14 S0 2 Me Me
26-15 CH2OMe Me 26-15 CH 2 OMe Me
26-16 CH20(CH2)2OMe Me Tabelle 27: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine n-Propylgruppe und R für Wasserstoff stehen und L die Brücke A364 bedeutet, worin die Reste R29, R 30 und R31 für Wasserstoff stehen 26-16 CH 2 0 (CH 2 ) 2 OMe Me Table 27: Compounds of the general formula (I) wherein Q is Q1, R x is an n-propyl group and R is hydrogen and L according to the invention means the bridge A364, in which the radicals R 29, R 30 and R 31 are hydrogen
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
27-1 Me H  27-1 Me H
27-2 Et H  27-2 Et H
27-3 Cl H  27-3 Cl H
27-4 OMe H  27-4 OMe H
27-5 CF3 H 27-5 CF 3 H
27-6 S02Me H 27-6 S0 2 Me H
27-7 Ch OMe H  27-7 Ch OMe H
27-8 CH20(CH2)2OMe H 27-8 CH 2 0 (CH 2 ) 2 OMe H
27-9 Me Me  27-9 Me Me
27-10 Et Me  27-10 Et Me
27-1 1 Cl Me  27-1 1 Cl Me
27-12 OMe Me  27-12 OMe Me
27-13 CF3 Me 27-13 CF 3 Me
27-14 S02Me Me 27-14 S0 2 Me Me
27-15 CH2OMe Me 27-15 CH 2 OMe Me
27-16 CH20(CH2)2OMe Me Tabelle 28: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2, Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A364 bedeutet, worin die Reste R29, R 30 und R31 für Wasserstoff stehen 27-16 CH 2 O (CH 2 ) 2 OMe Me Table 28: Compounds of the invention of the general formula (I) wherein Q is Q 2, R x is a methyl group and R is hydrogen and L is the bridge A364 in which R 29 , R 30 and R 31 are hydrogen
Tabelle 29: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q3, RY für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A364 bedeutet, worin die Reste R29, R 30 und R31 für Wasserstoff stehen Table 29: Compounds according to the invention of the general formula (I) in which Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A364, where R 29 , R 30 and R 31 are hydrogen
Tabelle 30: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q4, Rz für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A364 bedeutet, worin die Reste R29, R 30 und R31 für Wasserstoff stehen Table 30: Compounds of the invention of the general formula (I) wherein Q is Q4, R stand for a methyl group and R is hydrogen and L the bridge means A364 which the radicals R 29, R 30 and R 31 are hydrogen
Tabelle 31 : Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A365 bedeutet, worin die Reste R28, R30 und R31 für Wasserstoff stehen Table 31: Compounds of the invention of the general formula (I) wherein Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A365, wherein the radicals R 28 , R 30 and R 31 are hydrogen
Tabelle 32: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine Ethylgruppe und R für Wasserstoff stehen und L die Brücke A365 bedeutet, worin die Reste R28, R 30 und R31 für Wasserstoff stehen Table 32: Compounds of the invention of the general formula (I) in which Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A365, in which the radicals R 28 , R 30 and R 31 are hydrogen
Tabelle 33: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine n-Propylgruppe und R für Wasserstoff stehen und L die Brücke A365 bedeutet, worin die Reste R28, R30 und R31 für Wasserstoff stehen Table 33: Compounds of the invention of the general formula (I) in which Q is Q1, R x is an n-propyl group and R is hydrogen and L is the bridge A365 in which the radicals R 28 , R 30 and R 31 are hydrogen
Tabelle 34: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2, Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Table 34: Compounds of the invention of the general formula (I) in which Q is Q 2, R x is a methyl group and R is hydrogen and L is the
Brücke A365 bedeutet, worin die Reste R28, R30 und R31 für Wasserstoff stehen Bridge A365 means where R 28 , R 30 and R 31 are hydrogen
Tabelle 35: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q3, RY für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A365 bedeutet, worin die Reste R28, R30 und R31 für Wasserstoff stehen Table 35: Compounds of the invention of the general formula (I) in which Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A365 in which the radicals R 28 , R 30 and R 31 are hydrogen
Tabelle 36: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q4, Rz für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A365 bedeutet, worin die Reste R28, R 30 und R31 für Wasserstoff stehen Compounds of the invention of the general formula (I) wherein Q is Q4, R stand for a methyl group and R is hydrogen and L the bridge A365 means, in which the radicals R 28, R 30 and R 31 are hydrogen: Table 36
Tabelle 37: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A366 bedeutet, worin die Reste R28, R29 und R31 für Wasserstoff stehen Table 37: Compounds of the invention of the general formula (I) in which Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A366, in which R 28 , R 29 and R 31 are hydrogen
Tabelle 38: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine Ethylgruppe und R für Wasserstoff stehen und L die Brücke A366 bedeutet, worin die Reste R28, R29 und R31 für Wasserstoff stehen Table 38: Compounds according to the invention of the general formula (I) in which Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A366 in which the radicals R 28 , R 29 and R 31 are hydrogen
Tabelle 39: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine n-Propylgruppe und R für Wasserstoff stehen und L die Brücke A366 bedeutet, worin die Reste R28, R29 und R31 für Wasserstoff stehen Table 39: Compounds of the general formula (I) wherein Q is Q1, R x is an n-propyl group and R is hydrogen and L according to the invention means the bridge A366, in which the radicals R 28, R 29 and R 31 are hydrogen
Tabelle 40: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2, Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A366 bedeutet, worin die Reste R28, R29 und R31 für Wasserstoff stehen Table 40: Compounds of the invention of the general formula (I) wherein Q is Q 2, R x is a methyl group and R is hydrogen and L is the bridge A366 in which R 28 , R 29 and R 31 are hydrogen
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
40-1 Me H  40-1 Me H
40-2 Et H  40-2 Et H
40-3 Cl H  40-3 Cl H
40-4 OMe H  40-4 OMe H
40-5 CF3 H 40-5 CF 3 H
40-6 S02Me H 40-6 S0 2 Me H
40-7 CH2OMe H 40-7 CH 2 OMe H
40-8 CH20(CH2)2OMe H 40-8 CH 2 0 (CH 2 ) 2 OMe H
40-9 Me Me  40-9 Me Me
40-10 Et Me  40-10 et me
40-1 1 Cl Me  40-1 1 Cl Me
40-12 OMe Me  40-12 OMe Me
40-13 CF3 Me 40-13 CF 3 Me
40-14 S02Me Me 40-14 S0 2 Me Me
40-15 CH2OMe Me 40-15 CH 2 OMe Me
40-16 CH20(CH2)2OMe Me Tabelle 41 : Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q3, RY für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A366 bedeutet, worin die Reste R28, R29 und R31 für Wasserstoff stehen 40-16 CH 2 O (CH 2 ) 2 OMe Me Table 41: Compounds of the invention of the general formula (I) in which Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A366 in which the radicals R 28 , R 29 and R 31 are hydrogen
Tabelle 42: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q4, Rz für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A366 bedeutet, worin die Reste R28, R29 und R31 für Wasserstoff stehen Compounds of the invention of the general formula (I) wherein Q is Q4, R stand for a methyl group and R is hydrogen and L the bridge A366 means, in which the radicals R 28, R 29 and R 31 are hydrogen: Table 42
Tabelle 43: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A367 bedeutet, worin die Reste R28, R29 und R30 für Wasserstoff stehen Table 43: Compounds of the invention of the general formula (I) in which Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A367, in which R 28 , R 29 and R 30 are hydrogen
Tabelle 44: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine Ethylgruppe und R für Wasserstoff stehen und L die Brücke A367 bedeutet, worin die Reste R28, R29 und R30 für Wasserstoff stehen Table 44: Compounds of the invention of the general formula (I) in which Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A367, in which the radicals R 28 , R 29 and R 30 are hydrogen
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
44-1 Me H  44-1 Me H
44-2 Et H  44-2 Et H
44-3 Cl H  44-3 Cl H
44-4 OMe H  44-4 OMe H
44-5 CF3 H 44-5 CF 3 H
44-6 S02Me H 44-6 S0 2 Me H
44-7 CH2OMe H 44-7 CH 2 OMe H
44-8 CH20(CH2)2OMe H 44-8 CH 2 0 (CH 2 ) 2 OMe H
44-9 Me Me  44-9 Me Me
44-10 Et Me  44-10 Et Me
44-1 1 Cl Me  44-1 1 Cl Me
44-12 OMe Me  44-12 OMe Me
44-13 CF3 Me 44-13 CF 3 Me
44-14 S02Me Me 44-14 S0 2 Me Me
44-15 CH2OMe Me 44-15 CH 2 OMe Me
44-16 CH20(CH2)2OMe Me Tabelle 45: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine n-Propylgruppe und R für Wasserstoff stehen und L die Brücke A367 bedeutet, worin die Reste R28, R29 und R30 für Wasserstoff stehen 44-16 CH 2 O (CH 2 ) 2 OMe Me Table 45: Compounds of the invention of the general formula (I) in which Q is Q1, R x is an n-propyl group and R is hydrogen and L is the bridge A367, in which the radicals R 28 , R 29 and R 30 are hydrogen
Tabelle 46: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2, Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A367 bedeutet, worin die Reste R28, R29 und R30 für Wasserstoff stehen Table 46: Compounds of the invention of the general formula (I) in which Q is Q 2, R x is a methyl group and R is hydrogen and L is the bridge A367, in which R 28 , R 29 and R 30 are hydrogen
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
46-1 Me H  46-1 Me H
46-2 Et H  46-2 Et H
46-3 Gl H  46-3 Eq H
46-4 OMe H  46-4 OMe H
46-5 CF3 H 46-5 CF 3 H
46-6 S02Me H 46-6 S0 2 Me H
46-7 CH2OMe H 46-7 CH 2 OMe H
46-8 CH20(CH2)2OMe H 46-8 CH 2 0 (CH 2 ) 2 OMe H
46-9 Me Me  46-9 Me Me
46-10 Et Me  46-10 Et Me
46-1 1 Gl Me  46-1 1 Gl. Me
46-12 OMe Me  46-12 OMe Me
46-13 CF3 Me 46-13 CF 3 Me
46-14 S02Me Me 46-14 S0 2 Me Me
46-15 CH2OMe Me 46-15 CH 2 OMe Me
46-16 CH20(CH2)2OMe Me Tabelle 47: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q3, RY für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A367 bedeutet, worin die Reste R28, R29 und R30 für Wasserstoff stehen 46-16 CH 2 O (CH 2 ) 2 OMe Me Table 47: Compounds of the invention of the general formula (I) in which Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A367, in which R 28 , R 29 and R 30 are hydrogen
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
47-1 Me H  47-1 Me H
47-2 Et H  47-2 Et H
47-3 Cl H  47-3 Cl H
47-4 OMe H  47-4 OMe H
47-5 CF3 H 47-5 CF 3 H
47-6 S02Me H 47-6 S0 2 Me H
47-7 Ch OMe H  47-7 Ch OMe H
47-8 CH20(CH2)2OMe H 47-8 CH 2 0 (CH 2 ) 2 OMe H
47-9 Me Me  47-9 Me Me
47-10 Et Me  47-10 et me
47-1 1 Cl Me  47-1 1 Cl Me
47-12 OMe Me  47-12 OMe Me
47-13 CF3 Me 47-13 CF 3 Me
47-14 S02Me Me 47-14 S0 2 Me Me
47-15 CH2OMe Me 47-15 CH 2 OMe Me
47-16 CH20(CH2)2OMe Me Tabelle 48: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q4, Rz für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A367 bedeutet, worin die Reste R28, R29 und R30 für Wasserstoff stehen 47-16 CH 2 0 (CH 2 ) 2 OMe Me Compounds of the invention of the general formula (I) wherein Q is Q4, R z represent a methyl group and R is hydrogen and L the bridge A367 means, in which the radicals R 28, R 29 and R 30 are hydrogen: Table 48
Tabelle 49: Erfindungsgemäße Verbindungen der allgemeinen Formel (I) in Form der Natriumsalze, worin Q für Q1 , Rx für eine Methylgruppe und L die Brücke A30 bedeutet, worin die Reste R7 und R8 beide für Wasserstoff stehen Compounds of the invention of the general formula (I) in the form of sodium salts, wherein Q is Q1, R x is a methyl group and L the bridge A30 is wherein the radicals R 7 and R 8 are both hydrogen: Table 49
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
49-1 Me H  49-1 Me H
49-2 Et H  49-2 Et H
49-3 Cl H  49-3 Cl H
49-4 OMe H  49-4 OMe H
49-5 CF3 H 49-5 CF 3 H
49-6 S02Me H 49-6 S0 2 Me H
49-7 CH2OMe H 49-7 CH 2 OMe H
49-8 CH20(CH2)2OMe H 49-8 CH 2 0 (CH 2 ) 2 OMe H
49-9 Me Me  49-9 Me Me
49-10 Et Me  49-10 Et Me
49-1 1 Cl Me  49-1 1 Cl Me
49-12 OMe Me  49-12 OMe Me
49-13 CF3 Me 49-13 CF 3 Me
49-14 S02Me Me 49-14 S0 2 Me Me
49-15 CH2OMe Me 49-15 CH 2 OMe Me
49-16 CH20(CH2)2OMe Me Tabelle 50: Erfindungsgemäße Verbindungen der allgemeinen Formel (I) in Form der 49-16 CH 2 O (CH 2 ) 2 OMe Me Table 50: Compounds of the general formula (I) according to the invention in the form of
Natriumsalze, worin Q für Q , R* für eine Methylgruppe und L die Brücke A32 bedeutet, worin die Reste R7 und R8 beide für Wasserstoff stehen Sodium salts, wherein Q is Q, R * is a methyl group and L is the bridge A32, wherein the radicals R 7 and R 8 are both hydrogen
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
50-1 Me H  50-1 Me H
50-2 Et H  50-2 Et H
50-3 Cl H  50-3 Cl H
50-4 OMe H  50-4 OMe H
50-5 CF3 H 50-5 CF 3 H
50-6 S02 e H 50-6 S0 2 e H
50-7 Ch OMe H  50-7 Ch OMe H
50-8 CH20(CH2)2OMe H 50-8 CH 2 O (CH 2 ) 2 OMe H
50-9 Me Me  50-9 Me Me
50-10 Et Me  50-10 et me
50-1 1 Cl Me  50-1 1 Cl Me
50-12 OMe Me  50-12 OMe Me
50-13 CF3 Me 50-13 CF 3 Me
50-14 S02Me Me 50-14 S0 2 Me Me
50-15 CH2OMe Me 50-15 CH 2 OMe Me
50-16 CH20(CH2)2OMe Me Tabelle 51 : Erfindungsgemäße Verbindungen der allgemeinen Formel (I) in Form der Natriumsalze, worin Q für Q1 , Rx für eine Methylgruppe und L die Brücke A8 bedeutet, worin der Rest R7 für Wasserstoff steht 50-16 CH 2 O (CH 2 ) 2 OMe Me Table 51: Compounds of the invention of the general formula (I) in the form of sodium salts, wherein Q is Q1, R x is a methyl group and L represents the bridge A8, in which the radical R 7 is hydrogen
Nr. X W R8 Physikalische Daten (!H-NMR) No. XWR 8 Physical Data ( ! H-NMR)
51-1 Me H H  51-1 Me H H
51-2 Et H H  51-2 Et H H
51-3 Gl H H  51-3 HH
51-4 OMe H H  51-4 OMe H H
51-5 CF3 H H 51-5 CF 3 HH
51-6 S02Me H H 51-6 S0 2 Me HH
51-7 CH2OMe H H 51-7 CH 2 OMe HH
51-8 CH20(CH2)2OMe H H 51-8 CH 2 0 (CH 2 ) 2 OMe HH
51-9 Me Me H  51-9 Me Me H
51-10 Et Me H  51-10 Et Me H
51-1 1 Gl Me H  51-1 1 Gl Me H
51-12 OMe Me H  51-12 OMe Me H
51-13 CF3 Me H 51-13 CF 3 Me H
51-14 S02Me Me H 51-14 S0 2 Me Me H
51-15 CH2OMe Me H 51-15 CH 2 OMe Me H
51-16 CH20(CH2)2OMe Me H 51-16 CH 2 O (CH 2 ) 2 OMe Me H
51-17 Me H Me  51-17 Me H Me
51-18 Et H Me  51-18 Et H Me
51-19 Gl H Me  51-19 Gl H Me
51-20 OMe H Me  51-20 OMe H Me
51-21 CF3 H Me 51-21 CF 3 H Me
51-22 S02Me H Me 51-22 S0 2 Me H Me
51-23 CH2OMe H Me 51-23 CH 2 OMe H Me
51-24 CH20(CH2)2OMe H Me 51-24 CH 2 0 (CH 2 ) 2 OMe H Me
51-25 Me Me Me Nr. X W R8 Physikalische Daten (Ή-NMR)51-25 Me Me Me No. XWR 8 Physical Data (Ή-NMR)
51-26 Et Me Me 51-26 Et Me Me
51-27 Cl Me Me  51-27 Cl Me Me
51-28 OMe Me Me  51-28 OMe Me Me
51-29 CF3 Me Me 51-29 CF 3 Me Me
51-30 S02Me Me Me 51-30 S0 2 Me Me Me
51-31 Ch OMe Me Me  51-31 Ch OMe Me Me
51-32 CH20(CH2)2OMe Me Me 51-32 CH20 (CH 2) 2 OMe Me Me
Tabelle 52: Erfindungsgemäße Verbindungen der allgemeinen Formel (I) in Form der Table 52: Compounds of the general formula (I) according to the invention in the form of
Natriumsalze, worin Q für Q1 , Rx für eine Methylgruppe und L die Brücke A363 bedeutet, worin die Reste R28,R29, R30 und R31 für Wasserstoff stehen Sodium salts, wherein Q is Q1, R x is a methyl group and L is the bridge A363, wherein the radicals R 28 , R 29 , R 30 and R 31 are hydrogen
Nr. X W Physikalische Daten (1H-NMR) No. XW Physical Data ( 1 H-NMR)
52-1 Me H  52-1 Me H
52-2 Et H  52-2 Et H
52-3 Cl H  52-3 Cl H
52-4 OMe H  52-4 OMe H
52-5 CF3 H 52-5 CF 3 H
52-6 S02Me H 52-6 S0 2 Me H
52-7 CH2OMe H 52-7 CH 2 OMe H
52-8 CH20(CH2)2OMe H 52-8 CH 2 0 (CH 2 ) 2 OMe H
52-9 Me Me  52-9 Me Me
52-10 Et Me  52-10 Et Me
52-1 1 Cl Me  52-1 1 Cl Me
52-12 OMe Me  52-12 OMe Me
52-13 CF.3 Me Nr. X W Physikalische Daten (Ή-NMR) 52-13 CF.3 Me No. XW Physical Data (Ή-NMR)
52-14 S02Me Me 52-14 S0 2 Me Me
52-15 CH2OMe Me 52-15 CH 2 OMe Me
52-16 CH20(CH2)2OMe Me 52-16 CH 2 O (CH 2 ) 2 OMe Me
Tabelle 53: Erfindungsgemäße Verbindungen der allgemeinen Formel (I) in Form der Table 53: Compounds of the general formula (I) according to the invention in the form of
Natriumsalze, worin Q für Q1 , R* für eine Methylgruppe und L die Brücke A364 bedeutet, worin die Reste R29, R30 und R31 für Wasserstoff stehen Sodium salts, wherein Q is Q1, R * is a methyl group and L is the bridge A364, wherein the radicals R 29 , R 30 and R 31 are hydrogen
Nr. X W Physikalische Daten (1H-NMR) No. XW Physical Data ( 1 H-NMR)
53-1 Me H  53-1 Me H
53-2 Et H  53-2 Et H
53-3 Ci H  53-3 Ci H
53-4 OMe H  53-4 OMe H
53-5 CF3 H 53-5 CF 3 H
53-6 S02Me H 53-6 S0 2 Me H
53-7 CH2OMe H 53-7 CH 2 OMe H
53-8 CH20(CH2)2OMe H 53-8 CH 2 O (CH 2 ) 2 OMe H
53-9 Me Me  53-9 Me Me
53-10 Et Me  53-10 Et Me
53-1 1 CI Me  53-1 1 CI Me
53-12 OMe Me  53-12 OMe Me
53-13 CF3 Me 53-13 CF 3 Me
53-14 S02Me Me 53-14 S0 2 Me Me
53-15 CH2OMe Me 53-15 CH 2 OMe Me
53-16 CH20(CH2)2OMe Me Tabelle 54: Erfindungsgemäße Verbindungen der allgemeinen Formel (I) in Form der Natriumsalze, worin Q für Q , Rx für eine Methylgruppe und L die Brücke A365 bedeutet, worin die Reste R28, R30 und R31 für Wasserstoff stehen 53-16 CH 2 O (CH 2 ) 2 OMe Me Table 54: Compounds of the invention of the general formula (I) in the form of the sodium salts, in which Q is Q, R x is a methyl group and L is the bridge A365, where the radicals R 28 , R 30 and R 31 are hydrogen
Tabelle 55: Erfindungsgemäße Verbindungen der allgemeinen Formel (I) in Form der Natriumsalze, worin Q für Q1 , R* für eine Methylgruppe und L die Brücke A366 bedeutet, worin die Reste R28, R29 und R31 für Wasserstoff stehen Table 55: Compounds of the invention of the general formula (I) in the form of the sodium salts, wherein Q is Q1, R * is a methyl group and L is the bridge A366, wherein the radicals R 28 , R 29 and R 31 are hydrogen
Tabelle 56: Erfindungsgemäße Verbindungen der allgemeinen Formel (I) in Form der Natriumsalze, worin Q für Q1 , Rx für eine Methylgruppe und L die Brücke A367 bedeutet, worin die Reste R28, R29 und R30 für Wasserstoff stehen Compounds of the invention of the general formula (I) in the form of sodium salts, wherein Q is Q1, R x is a methyl group and L the bridge A367 means, in which the radicals R 28, R 29 and R 30 are hydrogen: Table 56
Tabelle 57: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 und R für Wasserstoff stehen und L die Brücke A6 bedeutet, worin die Reste R7 und R8 für Wasserstoff stehen Table 57: Compounds of the invention of the general formula (I) in which Q is Q1 and R is hydrogen and L is the bridge A6, in which the radicals R 7 and R 8 are hydrogen
Nr. Rx X W Physikalische Daten (Ή-NMR) No. R x XW Physical data (Ή-NMR)
57-24 Et CH20(CH2)2OMe H 57-24 Et CH 2 O (CH 2 ) 2 OMe H
57-25 Et Me Me (400 MHz, DMSO-de δ, ppm) 11.38  57-25 Et Me Me (400 MHz, DMSO-de δ, ppm) 11.38
(brs,1 H), 7.90 (d,1 H), 7.72 (d,1 H), 7.48 (s,1 H). 4.36 (q,2H), 2.69 (s,3H), 2.56 (s.3H). 1.49 (t,3H) (brs, 1H), 7.90 (d, 1H), 7.72 (d, 1H), 7.48 (s, 1H). 4.36 (q, 2H), 2.69 (s, 3H), 2.56 (s.3H). 1.49 (t, 3H)
57-26 Et Et Me 57-26 Et Et Me
57-27 Et Gl Me  57-27 Et Gl Me
57-28 Et O e Me  57-28 Et O e Me
57-29 Et CF3 Me 57-29 Et CF 3 Me
57-30 Et S02Me Me 57-30 Et S0 2 Me Me
57-31 Et CH2OMe Me 57-31 Et CH 2 OMe Me
57-32 Et CH20(CH2)2OMe Me 57-32 Et CH 2 O (CH 2 ) 2 OMe Me
Tabelle 58: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q fürTable 58: Compounds of the general formula (I) according to the invention, in which Q represents
Y für eine Methylgruppe und R für Wasserstoff stehen und L die  Y is a methyl group and R is hydrogen and L is the
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
58-1 Me H  58-1 Me H
58-2 Et H  58-2 Et H
58-3 Gl H  58-3 Eq H
58-4 OMe H  58-4 OMe H
58-5 CF3 H 58-5 CF 3 H
58-6 S02Me H 58-6 S0 2 Me H
58-7 CH2OMe H 58-7 CH 2 OMe H
58-8 CH20(CH2)2OMe H 58-8 CH 2 0 (CH 2 ) 2 OMe H
58-9 Me Me (400 MHz, DMSO-de δ, ppm) 7.99 (d,1 H), 7.70 (d, 1 H), 7.43  58-9 Me Me (400 MHz, DMSO-de δ, ppm) 7.99 (d, 1H), 7.70 (d, 1H), 7.43
(s,1 H), 3.30 (s,3H), 2.67 (s,3H), 2.40 (s,3H)  (s, 1H), 3.30 (s, 3H), 2.67 (s, 3H), 2.40 (s, 3H)
58-10 Et Me Nr. X W Physikalische Daten (Ή-NMR) 58-10 et me No. XW Physical Data (Ή-NMR)
58-1 1 Cl Me  58-1 1 Cl Me
58-12 OMe Me  58-12 OMe Me
58-13 CF3 Me 58-13 CF 3 Me
58-14 S02Me Me 58-14 S0 2 Me Me
58-15 CH2OMe Me 58-15 CH 2 OMe Me
58-16 CH20(CH2)2OMe Me 58-16 CH 2 O (CH 2 ) 2 OMe Me
Tabelle 59: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Table 59: Compounds of the general formula (I) according to the invention, in which Q denotes
Q1 und R für Wasserstoff stehen und L die Brücke A8 bedeutet, worin der Rest R7 für Wasserstoff steht Q1 and R are hydrogen and L is the bridge A8, wherein the radical R 7 is hydrogen
Tabelle 60: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Table 60: Compounds of the general formula (I) according to the invention, in which Q represents
Q3 und R für Wasserstoff stehen und L die Brücke A8 bedeutet, worin der Rest R7 für Wasserstoff steht Q3 and R are hydrogen and L is the bridge A8, wherein the radical R 7 is hydrogen
Tabelle 61 : Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A282 bedeutet, worin die Reste R12, R13, R14 und R15 für Table 61: Compounds of the invention of the general formula (I) wherein Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A282, wherein the radicals R 12 , R 13 , R 14 and R 15 is
Wasserstoff stehen  Hydrogen stand
Tabelle 62: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q Q1 , Rx für eine Ethylgruppe und R für Wasserstoff stehen und L die Brücke A282 bedeutet, worin die Reste R12, R13, R14 und R15 für Wasserstoff stehen Table 62: Compounds of the general formula (I) according to the invention wherein Q is Q1, R x is an ethyl group, and R is hydrogen and L the bridge A282 means, in which the radicals R 12, R 13, R 14 and R 15 are hydrogen
Tabelle 63: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine n-Propylgruppe und R für Wasserstoff stehen und L die Brücke A282 bedeutet, worin die Reste R12, R13, R14 und R15 für Table 63: Compounds of the invention of the general formula (I) in which Q is Q1, R x is an n-propyl group and R is hydrogen and L is the bridge A282 in which the radicals R 12 , R 13 , R 14 and R 15 For
Wasserstoff stehen  Hydrogen stand
Tabelle 64: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2, Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A282 bedeutet, worin die Reste R12, R13, R14 und R15 für Table 64: Compounds of the invention of the general formula (I) wherein Q is Q 2, R x is a methyl group and R is hydrogen and L is the bridge A282, wherein the radicals R 12 , R 13 , R 14 and R 15 are
Wasserstoff stehen  Hydrogen stand
Tabelle 65: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q3, RY für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A282 bedeutet, worin die Reste R12, R13, R14 und R15 für Table 65: Compounds of the invention of the general formula (I) wherein Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A282 in which the radicals R 12 , R 13 , R 14 and R 15 are
Wasserstoff stehen  Hydrogen stand
Tabelle 66: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q4, Rz für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A282 bedeutet, worin die Reste R12, R13, R14 und R15 für Table 66: Compounds of the invention of the general formula (I) wherein Q is Q4, R stand for a methyl group and R is hydrogen and L the bridge A282 means, in which the radicals R 12, R 13, R 14 and R 15 is
Wasserstoff stehen  Hydrogen stand
Tabelle 67: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A286 bedeutet, worin die Reste R12, R13, R14 und R15 für Table 67: Compounds of the invention of the general formula (I) wherein Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A286, wherein the radicals R 12 , R 13 , R 14 and R 15 are
Wasserstoff stehen  Hydrogen stand
Tabelle 68: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q Q1 , Rx für eine Ethylgruppe und R für Wasserstoff stehen und L die Brücke A286 bedeutet, worin die Reste R12, R13, R14 und R15 für Wasserstoff stehen Table 68: Compounds of the general formula (I) according to the invention wherein Q is Q1, R x is an ethyl group, and R is hydrogen and L the bridge A286 means, in which the radicals R 12, R 13, R 14 and R 15 are hydrogen
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
68-1 Me H  68-1 Me H
68-2 Et H  68-2 Et H
68-3 Cl H  68-3 Cl H
68-4 OMe H  68-4 OMe H
68-5 CF3 H 68-5 CF 3 H
68-6 S02Me H 68-6 S0 2 Me H
68-7 Ch OMe H  68-7 Ch OMe H
68-8 CH20(CH2)2OMe H 68-8 CH 2 0 (CH 2 ) 2 OMe H
68-9 Me Me  68-9 Me Me
68-10 Et Me  68-10 et me
68-1 1 Cl Me  68-1 1 Cl Me
68-12 OMe Me  68-12 OMe Me
68-13 CF3 Me 68-13 CF 3 Me
68-14 S02Me Me 68-14 S0 2 Me Me
68-15 CH2OMe Me 68-15 CH 2 OMe Me
68-16 CH20(CH2)2OMe Me Tabelle 69: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 , Rx für eine n-Propylgruppe und R für Wasserstoff stehen und L die Brücke A286 bedeutet, worin die Reste R12, R13, R14 und R15 für 68-16 CH 2 O (CH 2 ) 2 OMe Me Table 69: Compounds according to the invention of the general formula (I) in which Q is Q1, R x is an n-propyl group and R is hydrogen and L is the bridge A286, where the radicals R 12 , R 13 , R 14 and R 15 For
Wasserstoff stehen  Hydrogen stand
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
69-1 Me H  69-1 Me H
69-2 Et H  69-2 Et H
69-3 Gl H  69-3 H
69-4 OMe H  69-4 OMe H
69-5 CF3 H 69-5 CF 3 H
69-6 S02Me H 69-6 S0 2 Me H
69-7 CH2OMe H 69-7 CH 2 OMe H
69-8 CH20(CH2)2OMe H 69-8 CH 2 0 (CH 2 ) 2 OMe H
69-9 Me Me  69-9 Me Me
69-10 Et Me  69-10 Et Me
69-1 1 Gl Me  69-1 1 Gl. Me
69-12 OMe Me  69-12 OMe Me
69-13 CF3 Me 69-13 CF 3 Me
69-14 S02Me Me 69-14 S0 2 Me Me
69-15 CH2OMe Me 69-15 CH 2 OMe Me
69-16 CH20(CH2)2OMe Me Tabelle 70: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2, Rx für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A286 bedeutet, worin die Reste R12, R13, R14 und R15 für 69-16 CH 2 O (CH 2 ) 2 OMe Me Table 70: Compounds of the invention of the general formula (I) wherein Q is Q 2, R x is a methyl group and R is hydrogen and L is the bridge A286, wherein the radicals R 12 , R 13 , R 14 and R 15 is
Wasserstoff stehen  Hydrogen stand
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
70-1 Me H  70-1 Me H
70-2 Et H  70-2 Et H
70-3 Cl H  70-3 Cl H
70-4 OMe H  70-4 OMe H
70-5 CF3 H 70-5 CF 3 H
70-6 S02Me H 70-6 S0 2 Me H
70-7 CH2OMe H 70-7 CH 2 OMe H
70-8 CH20(CH2)2OMe H 70-8 CH 2 O (CH 2 ) 2 OMe H
70-9 Me Me  70-9 Me Me
70-10 Et Me  70-10 Et Me
70-1 1 Cl Me  70-1 1 Cl Me
70-12 OMe Me  70-12 OMe Me
70-13 CF3 Me 70-13 CF 3 Me
70-14 S02Me Me 70-14 S0 2 Me Me
70-15 CH2OMe Me 70-15 CH 2 OMe Me
70-16 CH20(CH2)2OMe Me Tabelle 71 : Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q3, RY für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A286 bedeutet, worin die Reste R12, R13, R14 und R15 für 70-16 CH 2 O (CH 2 ) 2 OMe Me Table 71: Compounds of the invention of the general formula (I) in which Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A286 in which the radicals R 12 , R 13 , R 14 and R 15 are
Wasserstoff stehen  Hydrogen stand
Tabelle 72: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q4, Rz für eine Methylgruppe und R für Wasserstoff stehen und L die Brücke A286 bedeutet, worin die Reste R12, R13, R14 und R15 für Compounds of the invention of the general formula (I) wherein Q is Q4, R stand for a methyl group and R is hydrogen and L the bridge A286 means, in which the radicals R 12, R 13, R 14 and R 15: Table 72
Wasserstoff stehen  Hydrogen stand
Tabelle 73: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q3, RY für Chlor und R für Wasserstoff stehen und L die Brücke A282 bedeutet, worin die Reste R12, R13, R14 und R15 für Wasserstoff stehen Table 73: Compounds of the invention of the general formula (I) in which Q is Q3, R Y is chlorine and R is hydrogen and L is the bridge A282 in which the radicals R 12 , R 13 , R 14 and R 15 are hydrogen
Nr. X W Physikalische Daten (Ή-NMR) No. X W Physical Data (Ή-NMR)
73-1 Me H  73-1 Me H
73-2 Et H  73-2 Et H
73-3 Cl H  73-3 Cl H
73-4 OMe H  73-4 OMe H
73-5 CF3 H 73-5 CF 3 H
73-6 S02 e H 73-6 S0 2 e H
73-7 Ch OMe H  73-7 Ch OMe H
73-8 CH20(CH2)2OMe H 73-8 CH 2 0 (CH 2 ) 2 OMe H
73-9 Me Me  73-9 Me Me
73-10 Et Me  73-10 Et Me
73-1 1 Cl Me  73-1 1 Cl Me
73-12 OMe Me  73-12 OMe Me
73-13 CF3 Me 73-13 CF 3 Me
73-14 S02Me Me 73-14 S0 2 Me Me
73-15 CH2OMe Me 73-15 CH 2 OMe Me
73-16 CH20(CH2)2OMe Me 73-16 CH 2 O (CH 2 ) 2 OMe Me
Tabelle 74: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q3, RY für Chlor und R für Wasserstoff stehen und L die Brücke A286 bedeutet, worin die Reste R12, R13, R14 und R15 für Wasserstoff stehen Table 74: Compounds of the invention of the general formula (I) in which Q is Q3, R Y is chlorine and R is hydrogen and L is the bridge A286 in which the radicals R 12 , R 13 , R 14 and R 15 are hydrogen
B. Formulierungsbeispiele a) Ein Stäubemittel wird erhalten, indem man 10 Gew. -Teile einer Verbindung der Formel (I) und/oder deren Salze und 90 Gew. -Teile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert. b) Ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem man 25 Gewichtsteile einer Verbindung der Formel (I) und/oder deren Salze, 64 Gew. -Teile kaolinhaltigen Quarz als Inertstoff, 10 Gewichtsteile B. Formulation Examples a) A dust is obtained by mixing 10 parts by weight of a compound of the formula (I) and / or salts thereof and 90 parts by weight of talc as an inert substance and comminuting in a hammer mill. b) A wettable powder readily dispersible in water is obtained by reacting 25 parts by weight of a compound of the formula (I) and / or its salts, 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight
ligninsulfonsaures Kalium und 1 Gew.-Teil oleoylmethyltaurinsaures Natrium als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt.  potassium lignosulfonate and 1 part by weight oleoylmethyltaurine sodium as wetting and dispersing agent and grinding in a pin mill.
) Ein in Wasser leicht dispergierbares Dispersionskonzentrat wird erhalten, indem man 20 Gew. -Teile einer Verbindung der Formel (I) und/oder deren Salze mit 6 Gew. -Teilen Alkylphenolpolyglykolether (©Triton X 207), 3 Gew. -Teilen A dispersion concentrate readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether (© Triton X 207), 3 parts by weight
Isotridecanolpolyglykolether (8 EO) und 71 Gew. -Teilen paraffinischem  Isotridecanol polyglycol ether (8 EO) and 71 parts by weight paraffinic
Mineralöl (Siedebereich z.B. ca. 255 bis über 277 C) mischt und in einer Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt. d) Ein emulgierbares Konzentrat wird erhalten aus 15 Gew. -Teilen einer  Mineral oil (boiling range, for example, about 255 to about 277 C) mixed and ground in a ball mill to a fineness of less than 5 microns. d) An emulsifiable concentrate is obtained from 15 parts by weight of a
Verbindung der Formel (I) und/oder deren Salze, 75 Gew. -Teilen Cyclohexanon als Lösungsmittel und 10 Gew. -Teilen oxethyliertes Nonylphenol als Emulgator.  Compound of formula (I) and / or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
) Ein in Wasser dispergierbares Granulat wird erhalten indem man ) A water-dispersible granules are obtained by
75 Gew. -Teile einer Verbindung der Formel (I) und/oder deren Salze,  75 parts by weight of a compound of the formula (I) and / or salts thereof,
10 Gew. -Teile ligninsulfonsaures Calcium,  10 parts by weight of lignosulfonic acid calcium,
5 Gew. -Teile Natriumlaurylsulfat,  5 parts by weight of sodium lauryl sulfate,
3 Gew. -Teile Polyvinylalkohol und  3 parts by weight of polyvinyl alcohol and
7 Gew. -Teile Kaolin  7 parts by weight kaolin
mischt, auf einer Stiftmühle mahlt und das Pulver in einem Wirbelbett durch Aufsprühen von Wasser als Granulierflüssigkeit granuliert.  milled, ground on a pin mill and granulated the powder in a fluidized bed by spraying water as Granulierflüssigkeit.
Ein in Wasser dispergierbares Granulat wird auch erhalten, indem man A water-dispersible granule is also obtained by
25 Gew. -Teile einer Verbindung der Formel (I) und/oder deren Salze,  25 parts by weight of a compound of the formula (I) and / or salts thereof,
5 Gew. -Teile 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium  5 parts by wt. 2,2'-dinaphthylmethane-6,6'-disulfonate sodium
2 Gew. -Teile oleoylmethyltaurinsaures Natrium,  2 parts by weight oleoylmethyltaurine acid sodium,
1 Gew.-Teil Polyvinylalkohol,  1 part by weight of polyvinyl alcohol,
17 Gew. -Teile Calciumcarbonat und  17 parts by weight calcium carbonate and
50 Gew. -Teile Wasser auf einer Kolloidmühle homogenisiert und vorzerkleinert, anschließend auf einer Perlmühle mahlt und die so erhaltene Suspension in einem Sprühturm mittels einer Einstoffdüse zerstäubt und trocknet. 50 parts by weight of water Homogenized on a colloid mill and pre-crushed, then grinded on a bead mill and the suspension thus obtained in a spray tower by means of a Einstoffdüse atomized and dried.
C. Biologische Beispiele C. Biological examples
1 . Herbizide Wirkung gegen Schadpflanzen im Vorauflauf  1 . Herbicidal action against weevils in pre-emergence
Samen von mono- bzw. dikotylen Unkraut- bzw. Kulturpflanzen werden in  Seeds of monocotyledonous or dicotyledonous weeds are cultivated in
Holzfasertöpfen in sandiger Lehmerde ausgelegt und mit Erde abgedeckt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen werden dann als wäßrige Suspension bzw.  Wood fiber pots laid in sandy loam soil and covered with soil. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
Emulsion mit einer Wasseraufwandmenge von umgerechnet 600 bis 800 l/ha unter Zusatz von 0,2% Netzmittel auf die Oberfläche der Abdeckerde appliziert. Nach der Behandlung werden die Töpfe im Gewächshaus aufgestellt und unter guten Emulsion with a water application rate of 600 to 800 l / ha with the addition of 0.2% wetting agent applied to the surface of the cover soil. After the treatment the pots are placed in the greenhouse and under good conditions
Wachstumsbedingungen für die Testpflanzen gehalten. Die visuelle Bonitur derMaintained growth conditions for the test plants. The visual rating of the
Schäden an den Versuchspflanzen erfolgt nach einer Versuchszeit von 3 Wochen im Vergleich zu unbehandelten Kontrollen (herbizide Wirkung in Prozent (%): 100% Wirkung = Pflanzen sind abgestorben, 0 % Wirkung = wie Kontrollpflanzen). Dabei zeigten beispielsweise die Verbindungen Nr. 17-19, 19-4, 57-25, 60-19, 60-51 , 60-147, 61 -1 und 67-1 bei einer Aufwandmenge von 320 g/ha eine mindestens 80%-igeDamage to the test plants occurs after a test period of 3 weeks in comparison to untreated controls (herbicidal action in percent (%): 100% effect = plants have died, 0% effect = like control plants). For example, compounds Nos. 17-19, 19-4, 57-25, 60-19, 60-51, 60-147, 61-1 and 67-1 at a rate of 320 g / ha exhibited at least 80%. owned
Wirkung gegen Veronica persica. Die Verbindungen Nr. 1 -1 , 17-19 und 60-1 15 zeigten bei einer Aufwandmenge von 320 g/ha eine mindestens 80%-ige Wirkung gegen Polygonum convolvulus und verursachten keinerlei Schäden in Mais und Weizen. Die Verbindungen Nr. 7-1 und 61-1 zeigten bei einer Aufwandmenge von 320 g/ha eine mindestens 80%-ige Wirkung gegen Cyperus serotinus und verursachten keinerlei Schäden in Weizen. Action against Veronica persica. The compounds Nos. 1 -1, 17-19 and 60-1 15 at an application rate of 320 g / ha showed at least 80% action against Polygonum convolvulus and caused no damage in corn and wheat. Compounds Nos. 7-1 and 61-1, at a rate of 320 g / ha, exhibited at least 80% activity against Cyperus serotinus and did not cause any damage to wheat.
2. Herbizide Wirkung gegen Schadpflanzen im Nachauflauf 2. Herbicidal action against harmful plants in postemergence
Samen von mono- bzw. dikotylen Unkraut- bzw. Kulturpflanzen werden in Seeds of monocotyledonous or dicotyledonous weeds are cultivated in
Holzfasertöpfen in sandigem Lehmboden ausgelegt, mit Erde abgedeckt und im Wood fiber pots laid out in sandy clay soil, covered with soil and in the
Gewächshaus unter guten Wachstumsbedingungen angezogen. 2 bis 3 Wochen nach der Aussaat werden die Versuchspflanzen im Einblattstadium behandelt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen werden dann als wäßrige Suspension bzw. Emulsion mit einer Wasseraufwandmenge von umgerechnet 600 bis 800 l/ha unter Zusatz von 0,2% Netzmittel auf die grünen Pflanzenteile gesprüht. Nach ca. 3 Wochen Standzeit der Versuchspflanzen im Gewächshaus unter optimalen Greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single leaf stage. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or Emulsion sprayed with an amount of water equivalent of 600 to 800 l / ha with the addition of 0.2% wetting agent on the green plant parts. After about 3 weeks life of the test plants in the greenhouse under optimal
Wachstumsbedingungen wird die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen bonitiert (herbizide Wirkung in Prozent (%): 100% Wirkung = Pflanzen sind abgestorben, 0 % Wirkung = wie Kontrollpflanzen). Dabei zeigten beispielsweise die Verbindungen Nr. 60-19, 60-147 und 67-1 bei einer Aufwandmenge von 80 g/ha eine mindestens 80%-ige Wirkung gegen Veronica persica. Die Growth conditions, the effect of the preparations is scored visually compared to untreated controls (herbicidal action in percent (%): 100% effect = plants are dead, 0% effect = like control plants). For example, Compound Nos. 60-19, 60-147 and 67-1 at an application rate of 80 g / ha exhibited at least 80% activity against Veronica persica. The
Verbindungen Nr. 59-51 und 67-1 zeigten bei einer Aufwandmenge von 80 g/ha eine mindestens 80%-ige Wirkung gegen Abutiion theophrasti und Pharbitis purpureum und verursachte keinerlei Schäden in Mais und Weizen. Die Verbindungen Nr. 17-19 und 61 -1 zeigten bei einer Aufwandmenge von 80 g/ha eine mindestens 80%-ige Wirkung gegen Amaranthus retroflexusund verursachte keinerlei Schäden in Reis und Weizen. Compound Nos. 59-51 and 67-1, at 80 g / ha, exhibited at least 80% activity against Abutiion theophrasti and Pharbitis purpureum and did not cause any damage to corn and wheat. Compound Nos. 17-19 and 61-1 at an application rate of 80 g / ha exhibited at least 80% activity against Amaranthus retroflexus and did not cause any damage to rice and wheat.

Claims

Patentansprüche claims
1. N-(Tetrazol-5-yl)-, N-(Triazol-5-yl)-, N-(1 ,2,5-Oxadiazol-3-yl)- und N-(1 ,3,4- Oxadiazol-2-yl)bicycloarylcarbonsäureamide der Formel (I) oder deren Salze 1. N- (tetrazol-5-yl), N- (triazol-5-yl), N- (1, 2,5-oxadiazol-3-yl) - and N- (1, 3,4-) Oxadiazol-2-yl) bicycloarylcarbonsäureamide of formula (I) or salts thereof
worin die Symbole und Indizes folgende Bedeutungen haben: wherein the symbols and indices have the following meanings:
Q bedeutet einen Rest Q1 , Q2, Q3 oder Q4, Q represents a remainder Q1, Q2, Q3 or Q4,
(Q1) (Q2) (Q3) (Q4)  (Q1) (Q2) (Q3) (Q4)
X bedeutet Nitro, Halogen, Cyano, Rhodano, (d-CeJ-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3- C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkenyl, Halogen-(C3-C6)- cycloalkenyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkenyl-(Ci-C6)-alkyl, R1(O)C, R1(R1ON=)C, R1O(O)C, (R1)2N(O)C, R1(RO)N(O)C, (R1)2N(R1)N(O)C, X denotes nitro, halogen, cyano, rhodano, (C 1 -C 6 -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogeno (C 2 -C 6 ) -alkenyl, ( C 2 -C 6) alkynyl, halo (C 3 -C 6) -alkynyl, (C 3 - C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (C 3 -C 6) cycloalkenyl, halo (C 3 -C 6) - cycloalkenyl, (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, halo (C 3 -C 6) -cycloalkyl- (Ci-C 6 ) alkyl, (C 3 -C 6) cycloalkenyl (Ci-C 6) alkyl, halo (C 3 -C 6) cycloalkenyl (Ci-C 6) alkyl, R 1 (O) C , R 1 (R 1 ON =) C, R 1 O (O) C, (R 1 ) 2 N (O) C, R 1 (RO) N (O) C, (R 1 ) 2 N (R 1 ) N (O) C
R1(O)C(R1)N(O)C, R2O(O)C(R1)N(O)C, (R1)2N(O)C(R1)N(O)C, R2(O)2S(R1)N(O)C, R1O(O)2S(R1)N(O)C, (R1)2N(O)2S(R1)N(O)C, RO, R1(O)CO, R2(O)2SO, R2O(O)CO, (R1)2N(O)CO,(R1)2N, R1(O)C(R1)N, R2(O)2S(R1)N, R2O(O)C(R1)N, (R1)2N(O)C(R1)N, R1O(O)2S(R1)N, (R1)2N(O)2S(R1)N, R (O)nS, R1O(O)2S, (R1)2N(O)2S, R 1 (O) C (R 1 ) N (O) C, R 2 O (O) C (R 1 ) N (O) C, (R 1 ) 2 N (O) C (R 1 ) N (O ) C, R 2 (O) 2 S (R 1 ) N (O) C, R 1 O (O) 2 S (R 1 ) N (O) C, (R 1 ) 2 N (O) 2 S ( R 1 ) N (O) C, RO, R 1 (O) CO, R 2 (O) 2 SO, R 2 O (O) CO, (R 1 ) 2 N (O) CO, (R 1 ) 2 N, R 1 (O) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N, R 2 O (O) C (R 1 ) N, (R 1 ) 2 N (O) C (R 1 ) N, R 1 O (O) 2 S (R 1 ) N, (R 1 ) 2 N (O) 2 S (R 1 ) N, R (O) n S, R 1 O (O) 2 S, (R 1 ) 2 N (O) 2 S,
R1(O)C(R1)N(O)2S, R2O(O)C(R1)N(O)2S, (R1)2N(O)C(R1)N(O)2S, (R5O)2(O)P, R1(O)C- (Ci-C6)-Alkyl, R1O(O)C-(Ci-C6)-Alkyl, (R1)2N(O)C-(Ci-C6)-Alkyl, (R1O)(R1)N(O)C-(Ci- C6)-Alkyi, (R1)2N(R1)N(O)C-(Ci-C6)-Alkyl, R1(O)C(R1)N(O)C-(Ci-C6)-Alkyl, R 1 (O) C (R 1 ) N (O) 2 S, R 2 O (O) C (R 1 ) N (O) 2 S, (R 1 ) 2 N (O) C (R 1 ) N (O) 2 S, (R 5 O) 2 (O) P, R 1 (O) C- (C 1 -C 6 ) -alkyl, R 1 O (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) C- (C 1 -C 6 ) -alkyl, (R 1 O) (R 1 ) N (O) C- (C 1 -C 6 ) -alkyi, (R 1 ) 2 N (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, R 1 (O) C (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl,
R2O(O)C(R1)N(O)C-(Ci-C6)-Alkyl, (R1)2N(O)C(R1)N(O)C-(Ci-C6)-Alkyl, R 2 O (O) C (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) C (R 1 ) N (O) C- (Ci-C 6 ) -alkyl,
R2(O)2S(R1)N(O)C-(Ci-C6)-Alkyl, R1O(O)2S(R1)N(O)C-(Ci-C6)-Alkyl, R 2 (O) 2 S (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, R 1 O (O) 2 S (R 1 ) N (O) C- (C 1 -C 6 ) alkyl,
(R1)2N(O)2S(R1)N(O)C-(Ci-C6)-Alkyl, NC-(Ci-C6)-Alkyl, R1O-(Ci-C6)-Alkyl, R1(O)CO- (Ci-C6)-Alkyl, R2(O)2SO-(Ci-C6)-Alkyl, R2O(O)CO-(Ci-C6)-Alkyl, (R1 )2N(O)CO-(Ci-C6)- Alkyl, (R1 )2N-(Ci-C6)-Alkyl, R1(O)C(R1 )N-(Ci-C6)-Alkyl, R2(O)2S(R1 )N-(Ci-C6)-Alkyl, R2O(O)C(R1 )N-(Ci-C6)-Alkyl, (R1 )2N(O)C(R1 )N-(Ci-C6)-A!kyl, R1O(O)2S(R1 )N-(Ci-C6)- Alkyi, (R1 )2N(O)2S(R1 )N-(Ci-C6)-Alkyl, R2(O)nS-(Ci-C6)-Alky!, R1O(O)2S-(Ci-C6)-Aikyl, (R1 )2N(O)2S-(Ci-C6)-Alkyl, R1(O)C(R1 )N(O)2S-(Ci-C6)-Alkyl, R2O(O)C(R1 )N(O)2S-(Ci- C6)-Alkyl, (R1 )2N(O)C(R1 )N(O)2S-(Ci-C6)-Alkyl, (R5O)2(O)P-(Ci-C6)-Alkyl, Phenyl, Heteroaryl, Heterocyclyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl- (Ci-C6)-alkyl, wobei die sechs letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, Cyano, Rhodano, (Ci-Ce)-Alkyl, Halogen-(Ci- C6)-alkyl, (C3-C6)-Cycloalkyl, R1O(O)C, (R1 )2N(O)C, R1O, (R1 )2N, R2(O)„S, R1O(O)2S, (R1 )2N(O)2S und RO-(Ci-C6)-Alkyl substituiert sind, und wobei Heterocyclyl n (R 1) 2 N (O) 2 S (R 1) N (O) C- (Ci-C 6) -alkyl, NC (Ci-C 6) alkyl, R 1 O- (Ci-C 6 ) -Alkyl, R 1 (O) CO- (C 1 -C 6 ) -alkyl, R 2 (O) 2 SO- (C 1 -C 6 ) -alkyl, R 2 O (O) CO- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N ( O) CO- (Ci-C 6) - alkyl, (R 1) 2 N- (Ci-C 6) alkyl, R 1 (O) C (R 1) N- (Ci-C 6) alkyl, R 2 (O) 2 S (R 1 ) N- (C 1 -C 6 ) -alkyl, R 2 O (O) C (R 1 ) N- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) C (R 1 ) N- (C 1 -C 6 ) -Alkyl, R 1 O (O) 2 S (R 1 ) N- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) 2 S (R 1 ) N- (C 1 -C 6 ) -alkyl, R 2 (O) n S- (C 1 -C 6 ) -alkyl, R 1 O (O) 2 S- (C 1 -C 4 ) -alkyl C 6 ) -alkyl, (R 1 ) 2 N (O) 2 S- (C 1 -C 6 ) -alkyl, R 1 (O) C (R 1 ) N (O) 2 S- (C 1 -C 6 ) -Alkyl, R 2 O (O) C (R 1 ) N (O) 2 S- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) C (R 1 ) N (O) 2 S - (C 1 -C 6 ) -alkyl, (R 5 O) 2 (O) P- (C 1 -C 6 ) -alkyl, phenyl, heteroaryl, heterocyclyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl- (Ci C6) -alkyl, heterocyclyl- (Ci-C6) -alkyl, wherein the six last mentioned radicals each by s radicals from the group consisting of nitro, halogen, cyano, Rhodano, (Ci-Ce) alkyl, halogen (Ci - C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, R 1 O (O) C, (R 1 ) 2 N (O) C, R 1 O, (R 1 ) 2 N, R 2 ( O) "S, R 1 O (O) 2 S, (R 1 ) 2 N (O) 2 S and RO- (C 1 -C 6 ) -alkyl, and wherein heterocyclyl n
Oxogruppen trägt, Wearing oxo groups,
W bedeutet Wasserstoff, Halogen, Nitro, Cyano, Rhodano, (Ci-C-6)-Alkyl, Halogen- (Ci-Ce)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3- C6)-alkinyl, (C3-C/)-Cycloalkyl, Halogen-(C3-C7)-cycloalkyl, (Ci-C6)-Alkoxy, Halogen- (Ci-Ce)-alkoxy, (Ci-C6)-Alkyl-(O)nS-, (Ci-C6)-Halogenalkyl-(O)nS-, (Ci-C6)-Alkoxy-(Ci-W is hydrogen, halogen, nitro, cyano, rhodano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogeno (C 2 -C 6 ) alkenyl, (C 2 -C 6) alkynyl, halo (C 3 - C 6) -alkynyl, (C 3 -C /) - cycloalkyl, halo (C 3 -C 7) cycloalkyl, (C -C 6) alkoxy, halo (Ci-Ce) alkoxy, (Ci-C 6) alkyl- (O) n S-, (Ci-C 6) -haloalkyl (O) n S-, ( Ci-C 6 ) -Alkoxy- (C
C4)-alkyl, (Ci-C6)-Alkoxy-(Ci-C4)-halogenalkyl, R1(O)C, R1(R1ON=)C, R1O(O)C, (R1 )2N, R1(O)C(R1 )N oder R2(O)2S(R1 )N, C 4 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -haloalkyl, R 1 (O) C, R 1 (R 1 ON =) C, R 1 O (O) C, ( R 1 ) 2 N, R 1 (O) C (R 1 ) N or R 2 (O) 2 S (R 1 ) N,
R bedeutet Wasserstoff, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyi, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)- cycloalkyl-(Ci-C6)-alkyl, R1(O)C-(Ci-C6)-Alkyl, RO(O)C-(Ci-C6)-Alkyl, (R1 )2N(O)C-(Ci- C6)-Alkyl, NC-(Ci-C6)-Alkyl, R1O-(Ci-C6)-Alkyl, R1(O)CO-(Ci-C6)-Alkyl, R2(O)2SO-(Ci- C6)-Alkyl, (R1 )2N-(Ci-C6)-Alkyl, R1(O)C(R1 )N-(Ci-C6)-Alkyl, R2(O)2S(R1 )N-(Ci-C6)-Alkyl, R2(O)nS-(Ci-C6)-Alkyl, R1O(O)2S-(Ci-C6)-Alkyl, (R1 )2N(O)2S-(Ci-C6)-Alkyl, R1(O)C, R1O(O)C, (R1 )2N(O)C, R1O, (R1 )2N, R2O(O)C(R1 )N, (R1 )2N(O)C(R1 )N, R2(O)2S, oder jeweils durch s Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Nitro, Trifluormethyl und Halogen substituiertes Benzyl, R is hydrogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 - C 6 ) -alkynyl, halogen- (C 3 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, halogen- (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (Ci-C 6) alkyl, halo (C 3 -C 6) - cycloalkyl- (Ci-C 6) alkyl, R 1 (O) C- (Ci-C 6) alkyl, RO (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) C- (C 1 -C 6 ) -alkyl, NC- (C 1 -C 6 ) -alkyl, R 1 O- (Ci-C 6) -alkyl, R 1 (O) CO- (Ci-C 6) alkyl, R 2 (O) 2 SO- (Ci- C6) alkyl, (R 1) 2 N- (Ci-C 6 ) -Alkyl, R 1 (O) C (R 1 ) N - (C 1 -C 6 ) -alkyl, R 2 (O) 2 S (R 1 ) N - (C 1 -C 6 ) -alkyl, R 2 ( O) n S- (C 1 -C 6 ) -alkyl, R 1 O (O) 2 S- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) 2 S- (C 1 -C 6 ) Alkyl, R 1 (O) C, R 1 O (O) C, (R 1 ) 2 N (O) C, R 1 O, (R 1 ) 2 N, R 2 O (O) C (R 1 ) N, (R 1 ) 2 N (O) C (R 1 ) N, R 2 (O) 2 S, or in each case by s radicals from the group consisting of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen substituted benzyl .
Rx bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2- Ce)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, wobei die sechs vorstehend genannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Cyano, (R6)3Si, (R50)2(0)P, R2(0)nS, (R1 )2N, R10, R1 (0)C, R10(0)C, R1(0)CO, R20(0)CO, R1(0)C(R1 )N, R2(0)2S(R1 )N, (C3-C6)-Cycloalkyl, Heteroaryi, Heterocyclyl und Phenyl substituiert sind, wobei die vier letztgenannten Reste durch s Reste aus der Gruppe bestehend aus (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-Ce)- alkoxy und Halogen substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, oder R x (Ci-C 6) alkyl, halo means (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 - Ce) alkenyl, (C 2 -C 6) Alkynyl, halogeno (C 3 -C 6) alkynyl, where the six radicals mentioned above are in each case represented by s radicals from the group consisting of nitro, cyano, (R 6) 3 Si, (R 5 0) 2 (0) P, R 2 (0) n S, (R 1) 2 N, R 1 is 0, R 1 (0) C, R 1 0 (0) C, R 1 (O) CO, R 2 O (0) CO, R 1 (O) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N, (C 3 -C 6 ) - Cycloalkyl, heteroaryl, heterocyclyl and phenyl are substituted, wherein the four latter radicals by s radicals from the group consisting of (Ci-C 6 ) alkyl, halogeno (Ci-C 6 ) alkyl, (Ci-Ce) alkoxy , Halogeno (C 1 -C 6) alkoxy and halogen, and wherein heterocyclyl carries n oxo groups, or
Rx bedeutet (C3-C/)-Cycloalkyl, Heteroaryi, Heterocyclyl oder Phenyl, wobei die vier vorstehend genannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-Ce)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (Ci-C6)-Alkyl- S(0)n, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci- C4)-alkyl substituiert sind, R x is (C 3 -C 6) -cycloalkyl, heteroaryl, heterocyclyl or phenyl, where the four radicals mentioned above are in each case represented by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6) -alkyl, halogen (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C6) alkyl- S (0) n, (Ci-Ce) alkoxy, halo (Ci-C 6) -alkoxy and (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -alkyl are substituted,
RY bedeutet Wasserstoff, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3~C7)-Cycloalkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (C2-C6)-Alkenyloxy, (C2-C6)-Alkinyloxy, Cyano, Nitro, Methylsulfenyl, Methyisulfinyl, Methyisulfonyl, Acetylamino, R Y is hydrogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, halo (C 3 -C 6) -alkynyl, (C 3 ~ C 7) cycloalkyl, (Ci-C 6) alkoxy, halo (Ci-C 6) alkoxy, ( C 2 -C 6 ) -alkenyloxy, (C 2 -C 6 ) -alkynyloxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino,
Benzoylamino, Methoxycarbonyl, Ethoxycarbonyl, Methoxycarbonylmethyl, Benzoylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl,
Ethoxycarbonylmethyl, Benzoyl, Methylcarbonyl, Piperidinylcarbonyl, Ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl,
Trifluormethylcarbonyl, Halogen, Amino, Aminocarbonyl, Methylaminocarbonyl, Dimethylaminocarbonyl, Methoxymethyl, Trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl,
oder jeweils durch s Reste aus der Gruppe bestehend aus (Ci-CeJ-Alkyl, Halogen- (Ci-Ce)-alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy und Halogen substituiertes Heteroaryi, Heterocyclyl oder Phenyl, und wobei Heterocyclyl n Oxogruppen trägt, Rz bedeutet Wasserstoff, (Ci-C6)-Alkyl, R1O-(Ci-C6)-Alkyl, R'CH2, (C3-C7)-or in each case by s radicals from the group consisting of (C 1 -C 6 -alkyl, halogeno (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxy, halogeno (C 1 -C 6) -alkoxy and halogen-substituted heteroaryl, heterocyclyl or phenyl, and where heterocyclyl carries n oxo groups, R z denotes hydrogen, (C 1 -C 6 ) -alkyl, R 1 O- (C 1 -C 6 ) -alkyl, R'CH 2 , (C 3 -C 7) -
Cycloalkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)- Alkinyl, Halogen-(C3-C6)-alkinyl, R1O, R1(H)N, Methoxycarbonyl, Ethoxycarbonyl, Methylcarbonyl, Dimethylamino, Trifluormethylcarbonyl, Acetylamino, Methylsulfenyl, Methyisulfinyl, Methyisulfonyl oder jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-Ce)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (Ci-C6)-Alkyl- S(O)n, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci- C4)-alkyl substituiertes Heteroaryi, Heterocyclyl, Benzyl oder Phenyl, wobei Cycloalkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6) - alkynyl, halo (C 3 -C 6) -alkynyl, R 1 O, R 1 (H) N, methoxycarbonyl, ethoxycarbonyl, methylcarbonyl, dimethylamino, trifluoromethylcarbonyl, acetylamino, methylsulfenyl, methylsulfinyl, methylsulfonyl or in each case by s radicals from the group consisting of halogen, nitro, cyano, (Ci-Ce) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 6) -alkyl- S (O) n, (Ci-Ce) - Alkoxy, halo (Ci-C 6 ) -alkoxy and (Ci-C 6 ) -Alkoxy- (Ci- C 4 ) alkyl substituted heteroaryl, heterocyclyl, benzyl or phenyl, wherein
Heterocyclyl n Oxogruppen trägt, R1 bedeutet Wasserstoff, (Ci-C6)-A!kyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloa!kenyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci- C6)-Alkyl-0-(Ci-C6)-a!kyi, Cycloalkyl-(Ci-C6)-aSkyl-0-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci- C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, Phenyl-0-(Ci-C6)-alkyl, Heteroaryl-0-(Ci-C6)-alkyl, Heterocyclyl-0-(Ci-C6)-alkyl, Phenyl-N(R3)-(Ci-C6)-alkyl, Heteroaryl-N(R3)-(Ci-C6)-alkyl, Heterocyclyl-N(R3)-(Ci-C6)- alkyl, Phenyl-S(0)n-(Ci-C6)-alkyl, Heteroaryl-S(0)n-(Ci-C6)-alkyl, Heterocyclyl-S(O)n- (Ci-CeJ-alkyl, wobei die fünfzehn letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, Cyano, Rhodano, (Ci-C-6)-Alkyl, Halogen-(Ci- C6)-alkyl, (C3-C6)-Cycloalkyl, R30(0)C, (R3)2N(0)C, R30, (R3)2N, R4(0)nS, R30(0)2S, (R3)2N(0)2S und R30-(Ci-C6)-Alkyl substituiert sind, und wobei Heterocyclyl n Heterocyclyl carries n oxo groups, R 1 represents hydrogen, (Ci-C 6) -A! Kyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, ( C 2 -C 6) alkynyl, halo (C 3 -C 6) -alkynyl, (C 3 -C 6) -cycloalkyl, (C3-C6) -alkenyl -Cycloa, halo (C 3 -C 6! ) cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, (Ci- C6) alkyl-0- (Ci-C6) -a! kyi, cycloalkyl- (Ci-C6 ) -aSkyl-O- (C 1 -C 6) -alkyl, phenyl, phenyl (C 1 -C 6) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6) -alkyl, Phenyl-O- (C 1 -C 6 ) -alkyl, heteroaryl-O- (C 1 -C 6 ) -alkyl, heterocyclyl-O- (C 1 -C 6 ) -alkyl, phenyl-N (R 3 ) - (C 1 -C 4) -alkyl C 6) alkyl, heteroaryl-N (R 3) - (Ci-C 6) alkyl, heterocyclyl-N (R 3) - (Ci-C 6) - alkyl, phenyl-S (0) n - (C -C 6 ) alkyl, heteroaryl-S (0) n- (Ci-C 6 ) alkyl, heterocyclyl-S (O) n - (Ci-CeJ-alkyl, wherein the fifteen latter radicals each by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (Ci-C 6) alkyl, halo (Ci- C6) alkyl, (C 3 -C 6) -cycloalkyl, R 3 0 (0) C (R 3 ) 2 N (0) C, R 3 O, (R 3 ) 2 N, R 4 (O) n S, R 3 O (0) 2 S, (R 3 ) 2 N (O) 2 S and R 3 are 0- (C 1 -C 6 ) -alkyl, and wherein heterocyclyl n
Oxogruppen trägt, R2 bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)- alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)- Cycloalkenyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)- Alkyl-0-(Ci-C6)-alkyl, Cycloalkyl-(Ci-C6)-alkyl-0-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)- alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, Phenyl-0-(Ci-C6)-alkyl, Heteroaryl-0-(Ci-C6)-alkyl, Heterocyclyl-0-(Ci-C6)-alkyl,Oxo groups carrying, R 2 is (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) - alkenyl, (C 2 -C 6) alkynyl, halo (C 3 -C 6) -alkynyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) - cycloalkenyl, halo (C 3 -C 6) - cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, (Ci-C 6) - alkyl-0- (Ci-C 6) alkyl, cycloalkyl (Ci-C 6) - alkyl-O- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6) -alkyl, Phenyl-0- (C 1 -C 6 ) -alkyl, heteroaryl-0- (C 1 -C 6 ) -alkyl, heterocyclyl-0- (C 1 -C 6 ) -alkyl,
Phenyl-N(R3)-(Ci-C6)-alkyl, Heteroaryl-N(R3)-(Ci-C6)-alkyl, Heterocyclyl-N(R3)-(Ci-C6)- alkyl, Phenyl-S(0)n-(Ci-C6)-alkyl, Heteroaryl-S(0)n-(Ci-C6)-alkyl, Heterocyclyl-S(0)M- (d-CeJ-alkyl, wobei die fünfzehn letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, Cyano, Rhodano, (Ci-Ce)-Alkyl, Halogen-(d- C6)-alkyl, (C3-C6)-Cycloalkyl, R30(0)C, (R3)2N(0)C, R30, (R3)2N, R4(0)nS, R30(0)2S, (R3)2N(0)2S und R30-(Ci-C6)-Alkyl substituiert sind, und wobei Heterocyclyl n Phenyl-N (R 3) - (Ci-C 6) alkyl, heteroaryl-N (R 3) - (Ci-C 6) alkyl, heterocyclyl-N (R 3) - (Ci-C 6) - alkyl , Phenyl-S (0) n - (C 1 -C 6 ) -alkyl, heteroaryl-S (0) n - (C 1 -C 6 ) -alkyl, heterocyclyl-S (O) M - (C 1 -C 6 -alkyl), where the fifteen last-mentioned radicals in each case by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (Ci-Ce) alkyl, halo (d- C6) alkyl, (C 3 -C 6) -cycloalkyl , R 3 0 (0) C, (R 3 ) 2 N (O) C, R 3 O, (R 3 ) 2 N, R 4 (O) n S, R 3 O (0) 2 S, (R 3 ) 2 N (O) 2 S and R 3 are 0- (C 1 -C 6 ) alkyl, and wherein heterocyclyl n
Oxogruppen trägt, Wearing oxo groups,
R3 bedeutet Wasserstoff, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, (C2- C6)-Alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 3 represents hydrogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 - C 6) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
R4 bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R5 bedeutet Wasserstoff oder (Ci-C4)-Alkyl, R 4 is (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (C 3 -C 6) Cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl, R 5 is hydrogen or (C 1 -C 4 ) -alkyl,
R6 bedeutet (Ci-C4)-Alkyl, R' bedeutet Acetoxy, Acetamido, N-Methylacetamido, Benzoyloxy, Benzamido, N- Methylbenzamido, Methoxycarbonyl, Ethoxycarbonyl, Benzoyl, Methylcarbonyl, Piperidinylcarbonyl, Morpholinylcarbonyl, Trifluormethylcarbonyl, Aminocarbonyl, Methylaminocarbonyl, DimethySaminocarbonyl, (C3-C6)-Cycloalkyl oder jeweils durch s Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl und Halogen substituiertes Heteroaryl oder Heterocyclyl, n bedeutet 0, 1 oder 2, m bedeutet 0, 1 , 2, 3 oder 4, s bedeutet 0, 1 , 2 oder 3, t bedeutet 0, 1 , 2, 3, 4 oder 5, L bedeutet eine 3-, 4- oder 5-gliedrige ankondensierte, ungesättigte Brücke, deren Brückenatome aus t Kohlenstoffatomen und m Heteroatomen aus der Gruppe bestehend aus O, S und N bestehen. R 6 is (C 1 -C 4 ) -alkyl, R 'is acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethyaminocarbonyl , (C 3 -C 6) -cycloalkyl or in each case by s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen-substituted heteroaryl or heterocyclyl, n is 0, 1 or 2, m is 0, 1, 2, 3 or 4, s is 0, 1, 2 or 3, t is 0, 1, 2, 3, 4 or 5, L is a 3-, 4- or 5-membered fused, unsaturated bridge whose bridging atoms are composed of t carbon atoms and m Heteroatoms consist of the group consisting of O, S and N.
2. N-(Tetrazol-5-yl)-, N-(Triazol-5-yl)-, N-(1 ,2,5-Oxadiazol-3-yl)- und N-(1 ,3,4- Oxadiazol-2-yl)bicycloarylcarbonsäureamide nach Anspruch 1 , worin die Brücke L für die Reste A1 bis A378 steht, wobei die gestrichelten Bindungen diejenigen Bindungen darstellen, welche die Brücke L an den Benzoylrest anbinden. Hierbei stellt die obere gestrichelte Linie die Bindung an das C-Atom 3 der allgemeinen Formel (I) und die untere gestrichelte Linie die Bindung an das C-Atom 4 der allgemeinen Formel (I) dar: 2. N- (tetrazol-5-yl), N- (triazol-5-yl), N- (1, 2,5-oxadiazol-3-yl) - and N- (1, 3,4-) Oxadiazol-2-yl) bicycloarylcarbonsäureamide according to claim 1, wherein the bridge L is the radicals A1 to A378, wherein the dashed bonds represent those bonds which attach the bridge L to the benzoyl radical. Here, the upper dashed line represents the bond to the C atom 3 of the general formula (I) and the lower dashed line represents the bond to the C atom 4 of the general formula (I):
(AD (A2) (A3) (A4) (A5) (A6) (AD (A2) (A3) (A4) (A5) (A6)
(A7) (A8) (A9) (A10) (A11) (A12) (A7) (A8) (A9) (A10) (A11) (A12)
(A13) (A14) (A15) (A16) (A17) (A18) (A13) (A14) (A15) (A16) (A17) (A18)
(A19) (A20) (A21) (A22) (A23) (A24) (A19) (A20) (A21) (A22) (A23) (A24)
(A25) (A26) (A27) (A28) (A29) (A30) (A25) (A26) (A27) (A28) (A29) (A30)
(A31 ) (A32) (A33) (A34) (A35) (A36) (A31) (A32) (A33) (A34) (A35) (A36)
(A43) (A44) (A45) (A46) (A47) (A48) (A43) (A44) (A45) (A46) (A47) (A48)
(A49) (A50) (A51) (A52) (A49) (A50) (A51) (A52)
(A61) (A62) (A63) (A64) (A65) (A66) (A61) (A62) (A63) (A64) (A65) (A66)
(A67) (A68) (A69) (A70) (A71) (A72) A73) (A67) (A68) (A69) (A70) (A71) (A72) A73)
(A74) (A75) (A76) (A77) (A78) (A79) (A80) (A74) (A75) (A76) (A77) (A78) (A79) (A80)
(A81) (A82) (A83) (A84) (A85) (A86) (A87) (A81) (A82) (A83) (A84) (A85) (A86) (A87)
(A94) (A95) (A96) (A97) (A98) (A94) (A95) (A96) (A97) (A98)
(A100) (A101) (A102) (A104) (A105) (A100) (A101) (A102) (A104) (A105)
(A106) (A107) (A108) (A109) (A110) (A111) (A112) (A106) (A107) (A108) (A109) (A110) (A111) (A112)
(A114) (A116) (A117) (A118) (A119) (A114) (A116) (A117) (A118) (A119)
(A122) (A123) (A124) (A125) (A126) (A122) (A123) (A124) (A125) (A126)
(A127) (A128) (A129) (A130) (A131) (A132) (A127) (A128) (A129) (A130) (A131) (A132)
(A133) (A134) (A135) (A136) (A137)  (A133) (A134) (A135) (A136) (A137)
(A151) (A152) (A153) (A155) (A156) (A157)  (A151) (A152) (A153) (A155) (A156) (A157)
(A161) (A162) (A163) (A161) (A162) (A163)
(A164) (A165) (A166) (A167) (A164) (A165) (A166) (A167)
(A169) (A170) (A171) (A172) (A169) (A170) (A171) (A172)
(A178) (A179) (A180) (A181) (A182) (A178) (A179) (A180) (A181) (A182)
(A183) (A184) (A185) (A186) (A187) (A183) (A184) (A185) (A186) (A187)
(A188) (A189) (A190) (A191) (A192) (A188) (A189) (A190) (A191) (A192)
(A193) (A194) (A195) (A196) (A193) (A194) (A195) (A196)
(A221 ) (A222) (A223) (A224) (A225) (A226) (A221) (A222) (A223) (A224) (A225) (A226)
(A233) (A234) (A235) (A236) (A237) (A238) (A233) (A234) (A235) (A236) (A237) (A238)
(A239) (A240) (A241) (A242) (A243) (A244)  (A239) (A240) (A241) (A242) (A243) (A244)
(A257) (A258) (A259) (A260) (A261) (A262)  (A257) (A258) (A259) (A260) (A261) (A262)
(A263) (A264) (A265) (A266) (A267) (A268)  (A263) (A264) (A265) (A266) (A267) (A268)
O O
O. ,0 II O. .0 O ,0  O., 0 II O. .0 O, 0
N N -' N NN - ' N
II II ' il II II II II . II
"T " T
o o o T  o o o T
o  O
(A269) (A270) (A271) (A272) (A273) (A269) (A270) (A271) (A272) (A273)
(A274) (A275) (A276) (A277) (A278) (A279) (A274) (A275) (A276) (A277) (A278) (A279)
(A280) (A281 ) (A282) (A283) (A284) (A285) (A280) (A281) (A282) (A283) (A284) (A285)
(A286) (A287) (A288) (A289) (A290) (A291 ) (A286) (A287) (A288) (A289) (A290) (A291)
(A292) (A293) (A294) (A295) (A296) (A297) (A292) (A293) (A294) (A295) (A296) (A297)
(A304) (A305) (A306) (A307) (A308) (A309) (A304) (A305) (A306) (A307) (A308) (A309)
(A310) (A31 1 ) (A312) (A310) (A31 1) (A312)
(A313) (A314) (A315) (A316) (A317) (A318) (A319) (A313) (A314) (A315) (A316) (A317) (A318) (A319)
(A320) (A321 ) (A322) (A323) (A324) (A325) (A326) (A320) (A321) (A322) (A323) (A324) (A325) (A326)
(A327) (A328) (A329) (A330) (A331 ) (A332) (A333) (A327) (A328) (A329) (A330) (A331) (A332) (A333)
(A336) (A337) (A338) (A339) (A340) (A336) (A337) (A338) (A339) (A340)
(A341 ) (A342) (A343) (A344) (A345) (A346) (A347) (A341) (A342) (A343) (A344) (A345) (A346) (A347)
(A348) (A349) (A350) (A351 ) (A348) (A349) (A350) (A351)
(A352) (A353) (A354) (A355) (A356) (A357)  (A352) (A353) (A354) (A355) (A356) (A357)
(A358) (A359) (A360) (A361 ) (A362)  (A358) (A359) (A360) (A361) (A362)
(A363) (A364) (A365) (A366) (A367) (A368)  (A363) (A364) (A365) (A366) (A367) (A368)
A369) (A370) (A371 ) (A372) (A373) (A374) A369) (A370) (A371) (A372) (A373) (A374)
(A375) (A376) (A377) (A378) (A375) (A376) (A377) (A378)
R7, R8, R12, R13, R22 und R23 bedeuten unabhängig voneinander jeweils R 7 , R 8 , R 12 , R 13 , R 22 and R 23 are each independently
Wasserstoff, Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen- (C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen- (C3-C6)-cycloalkyl, (C3-C6)-Cycloalkenyl, Halogen-(C3-C6)-cycloalkenyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, (C3-C6)- Cyc!oalkenyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cyc!oalkenyl-(Ci-C6)-alkyl, R1(0)C, R1(R1ON=)C, R10(0)C, (R1)2N(0)C, R1(R10)N(0)C, (R1)2N(R1)N(0)C, Hydrogen, halogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 - C 6) alkynyl, halo (C 3 -C 6) -alkynyl, (C 3 -C 6) cycloalkyl, halo (C3-C6) cycloalkyl, (C 3 -C 6) cycloalkenyl, halogen - (C 3 -C 6) cycloalkenyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, halo (C3-C6) cycloalkyl- (Ci-C 6) alkyl, (C 3 -C 6 ) - Cycloalkenyl- (C 1 -C 6 ) -alkyl, halo (C 3 -C 6 ) -cycloalkenyl- (C 1 -C 6 ) -alkyl, R 1 (O) C, R 1 (R 1 ON =) C R 1 0 (0) C (R 1) 2 N (0) C, R 1 (R 1 0) N (0) C (R 1) 2 N (R 1) N (0) C,
R1(0)C(R1)N(0)C, R20(0)C(R1)N(0)C, (R1)2N(0)C(R1)N(0)C, R2(0)2S(R1)N(0)C, R10(0)2S(R1)N(0)C, (R1)2N(0)2S(R1)N(0)C, R20, R1(0)CO, R2(0)2SO, R20(0)CO, (R1)2N(0)CO, (R1)2N, R1(0)C(R1)N, R2(0)2S(R1)N, R20(0)C(R1)N, (R1)2N(0)C(R1)N, R10(0)2S(R1)N, (R1)2N(0)2S(R1)N, R2(0)nS, R10(0)2S, (R1)2N(0)2S, R 1 (0) C (R 1 ) N (0) C, R 2 0 (0) C (R 1 ) N (O) C, (R 1 ) 2 N (O) C (R 1 ) N (0 ) C, R 2 (O) 2 S (R 1 ) N (O) C, R 1 O (O) 2 S (R 1 ) N (O) C, (R 1 ) 2 N (O) 2 S ( R 1 ) N (O) C, R 2 O, R 1 (O) CO, R 2 (O) 2 SO, R 2 O (0) CO, (R 1 ) 2 N (O) CO, (R 1 ) 2 N, R 1 (O) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N, R 2 O (0) C (R 1 ) N, (R 1 ) 2 N (0 ) C (R 1) N, R 1 0 (0) 2 S (R 1) N, (R 1) 2 N (0) 2 S (R 1) N, R 2 (0) n S, R 1 0 (0) 2 S, (R 1 ) 2 N (0) 2 S,
R1(0)C(R1)N(0)2S, R20(0)C(R1)N(0)2S, (R1)2N(0)C(R1)N(0)2S, R1(0)C-(Ci-C6)-Alkyl, RO(0)C-(Ci-C6)-Alkyl, (R1)2N(0)C-(Ci-C6)-Alkyl, (R10)(R1)N(0)C-(Ci-C6)-Alkyl, (R1)2N(R1)N(0)C-(Ci-C6)-Alkyl, R1(0)C(R1)N(0)C-(Ci-C6)-Alkyl, R20(0)C(R1)N(0)C- (Ci-C6)-Alkyl, (R1)2N(0)C(R1)N(0)C-(Ci-C6)-Alkyl, R2(0)2S(R1)N(0)C-(Ci-C6)-Alkyl, R10(0)2S(R1)N(0)C-(Ci-C6)-Alkyl, (R1)2N(0)2S(R1)N(0)C-(Ci-C6)-Alkyl, NC-(Ci-Ce)- Alkyl, R10-(Ci-C6)-Alkyl, R1(0)CO-(Ci-C6)-Alkyl, R2(0)2SO-(Ci-C6)-Alkyl, R20(0)CO- (Ci-C6)-Alkyl, (R1)2N(0)CO-(Ci-C6)-Alkyl, (R1)2N-(Ci-C6)-Alkyl, R1(0)C(R1)N-(Ci-C6)- Alkyl, R2(0)2S(R1)N-(Ci-C6)-Alkyl, R20(0)C(R1)N-(Ci-C6)-Alkyl, (R1)2N(0)C(R1)N-(Ci- C6)-Alkyl, R10(0)2S(R1)N-(Ci-C6)-Alkyl, (R1)2N(0)2S(R1)N-(Ci-C6)-Alkyl, R2(0)„S-(Ci- C6)-Alkyl, R10(0)2S-(Ci-C6)-Alkyl, (R1)2N(0)2S-(Ci-C6)-Alkyl, R1(0)C(R1)N(0)2S-(Ci- C6)-Alkyl, R20(0)C(R1)N(0)2S-(Ci-C6)-Alkyl, (R1)2N(0)C(R1)N(0)2S-(Ci-C6)-AIky!, (R50)2(0)P-(Ci-C6)-Alkyl, Phenyl, Heteroaryl, Heterocyclyl, Phenyl-(Ci-C6)-aikyl, Heteroaryl-(Ci-C6)-a!kyl, Heterocyclyl-(Ci-C6)-alkyl, wobei die sechs letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, Cyano, Rhodano, (Ci-Ce)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, R10(0)C, R 1 (O) C (R 1 ) N (O) 2 S, R 2 O (0) C (R 1 ) N (O) 2 S, (R 1 ) 2 N (O) C (R 1 ) N (0) 2 S, R 1 (0) C- (C 1 -C 6 ) -alkyl, RO (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) C- (Ci -C 6) alkyl, (R 1 0) (R 1) N (0) C- (Ci-C 6) -alkyl, (R 1) 2 N (R 1) N (0) C- (Ci- C 6 ) -alkyl, R 1 (O) C (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, R 2 0 (0) C (R 1 ) N (O) C- (Ci -C 6 ) alkyl, (R 1 ) 2 N (O) C (R 1 ) N (O) C- (C 1 -C 6 ) alkyl, R 2 (O) 2 S (R 1 ) N (0 ) C- (C 1 -C 6 ) -alkyl, R 1 0 (0) 2 S (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) 2 S (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, N-C- (C 1 -C 6 ) -alkyl, R 1 0- (C 1 -C 6 ) -alkyl, R 1 (O) CO- ( Ci-C 6 ) alkyl, R 2 (0) 2 SO- (Ci-C 6 ) -alkyl, R 2 0 (0) CO- (Ci-C 6 ) -alkyl, (R 1 ) 2 N (0 ) CO- (Ci-C 6) alkyl, (R 1) 2 N- (Ci-C 6) alkyl, R 1 (0) C (R 1) N- (Ci-C 6) - alkyl, R 2 (0) 2 S (R 1 ) N- (C 1 -C 6 ) -alkyl, R 2 0 (0) C (R 1 ) N- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N ( 0) C (R 1 ) N- (C 1 -C 6 ) -alkyl, R 1 0 (O) 2 S (R 1 ) N- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (0) 2 S (R 1 ) N- (C 1 -C 6 ) -alkyl, R 2 (O) "S- (C 1 -C 6 ) -alkyl, R 1 0 (O) 2 S- (C 1 -C 6 ) - Alkyl, (R 1 ) 2 N (O) 2 S- (C 1 -C 6 ) -alkyl, R 1 (O) C (R 1 ) N (0) 2 S- (C 1 -C 6 ) -alkyl, R 2 0 (0) C (R 1 ) N (O) 2 S- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (0) C (R 1 ) N (O) 2 S- (C 1 -C 6 ) -alkyl, (R 5 O) 2 (O) P- (C 1 -C 6 ) -alkyl, phenyl, heteroaryl, Heterocyclyl, phenyl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, where the six last-mentioned radicals are each represented by s radicals from the group consisting of nitro , halogen, cyano, thiocyanato, (Ci-Ce) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, R 1 0 (0) C,
(R1)2N(0)C, R10, (R1)2N, R2(0)nS, R10(0)2S, (R1)2N(0)2S und R10-(Ci-C6)-Alkyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R9, R10, R14, R15, R16, R17, R20, R21, R24 und R25 bedeuten unabhängig voneinander jeweils Wasserstoff, Halogen, (Ci-C4)-Alkyl, (Ci-C4)-Halogenalkyl, (Ci-C4)-Alkoxy, (Ci- C4)-Halogenalkoxy oder (Ci-C4)-Alkoxy-(Ci-C4)-alkyl oder je zwei geminale R9, R10, R14, R15, R16, R17, R20, R21, R24 und R25 bilden gemeinsam mit dem Kohlenstoffatom, an das sie gebunden sind, eine Carbonylgruppe oder ein(R 1 ) 2 N (O) C, R 1 O, (R 1 ) 2 N, R 2 (O) n S, R 1 O (0) 2 S, (R 1 ) 2 N (O) 2 S and R 1 is 0- (C 1 -C 6 ) -alkyl, and wherein heterocyclyl carries n oxo groups, R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 independently of one another are each hydrogen, halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkoxy or (C 1 -C 4) -alkoxy (Ci-C4) -alkyl or two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 together form the carbon atom to which they are attached are, a carbonyl group or a
Oxim der Formel C=NOR1 oder Oxime of the formula C = NOR 1 or
je zwei geminale R9, R10, R14, R15, R16, R17, R20, R21, R24 und R25 bedeuten ein Acetal der Formel -0-(C2-C4)-Alkylen-0-, R11, R18, R19, R26 und R27 bedeuten unabhängig voneinander jeweils Wasserstoff, (Ci- C6)-Alkyl, Ha!ogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)- Aikinyl, Halogen-(C3-C6)-alkinyi, wobei die sechs vorstehend genannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Cyano, R2(0)nS, (R1 )2N , R10, R1(0)C, R10(0)C, R1(0)CO, R20(0)CO, R1(0)C(R1)N, R2(0)2S(R1)N, (C3-C6)- Cycloalkyl, Heteroaryl, Heterocyclyl und Phenyl substituiert sind, wobei die vier letztgenannten Reste durch s Reste aus der Gruppe bestehend aus (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-CeJ-Alkoxy, Halogen-(Ci-C6)-alkoxy und Halogen substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, oder R11, R18, R19, R26 und R27 bedeuten unabhängig voneinander jeweils (C3-C7)- Cycloalkyl, Heteroaryl, Heterocyclyl oder Phenyl, wobei die vier vorstehend genannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C -C6)-Cycloalkyl, (Ci-C6)-Alkyl- S(0)n, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C4)-alkyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, in each case two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 are acetals of the formula -O- (C 2 -C 4) -alkylene-O - R 11, R 18, R 19, R 26 and R 27 are each independently hydrogen, (Ci- C 6) alkyl, Ha Ogen (Ci-C 6) alkyl, (C 2 -C 6)! - Alkenyl, halo (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, halo (C 3 -C 6 ) -alkynyl, where the six radicals mentioned above are in each case represented by s radicals from the group consisting of nitro , cyano, R 2 (0) n S, (R 1) 2 N, R 1 is 0, R 1 (0) C, R 1 0 (0) C, R 1 (0) CO, R 2 0 (0) CO , R 1 (O) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N, (C 3 -C 6 ) -cycloalkyl, heteroaryl, heterocyclyl and phenyl are substituted, wherein the four latter radicals by s radicals are substituted from the group consisting of (C 1 -C 6) -alkyl, halogeno (C 1 -C 6) -alkyl, (C 1 -C 6 -alkoxy, halogeno (C 1 -C 6) -alkoxy and halogen, and where heterocyclyl n Oxo groups, or R 11 , R 18 , R 19 , R 26 and R 27 are each independently (C3-C7) - cycloalkyl, heteroaryl, heterocyclyl or phenyl, wherein the four radicals mentioned above each consisting of s radicals from the group from halogen , Nitro, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C-C6) cycloalkyl, (Ci-C6) alkyl- S (0) n, ( C 1 -C 6 ) alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) -alkoxy- (C 1 -C 4) -alkyl, and where heterocyclyl carries n oxo groups,
R28, R29, R30 und R31 bedeuten unabhängig voneinander jeweils Wasserstoff, Nitro, Halogen, Cyano, Rhodano, (Ci-Ce)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkenyl, Halogen-(C3-C6)-cycloalkenyl, (C3- C6)-Cycloalkyl-(Ci-C6)-aikyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, (C3-C6)- Cycloalkenyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkenyl-(Ci-C6)-alkyl, R1(O)C, R1(R1ON=)C, R1O(O)C, (R1)2N(O)C, R1(R1O)N(O)C, (R1)2N(R1)N(O)C, R 28, R 29, R 30 and R 31 are each independently hydrogen, nitro, halogen, cyano, thiocyanato, (Ci-Ce) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6 ) Alkenyl, halo (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, halo (C 3 -C 6 ) alkynyl, (C 3 -C 6 ) cycloalkyl, halogen (C 3 -C 6) -cycloalkyl, (C3-C6) cycloalkenyl, halo (C 3 -C 6) cycloalkenyl, (C 3 - C 6) -cycloalkyl- (Ci-C 6) -alkyl, halogen (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkenyl, (Ci-C 6) alkyl, halo (C 3 -C 6) cycloalkenyl (C 1 -C 6 ) -alkyl, R 1 (O) C, R 1 (R 1 ON =) C, R 1 O (O) C, (R 1 ) 2 N (O) C, R 1 (R 1 O) N (O) C, (R 1 ) 2 N (R 1 ) N (O) C,
R1(O)C(R1)N(O)C, R2O(O)C(R1)N(O)C, (R1)2N(O)C(R1)N(O)C, R2(O)2S(R1)N(O)C, R1O(O)2S(R1)N(O)C, (R1)2N(O)2S(R1)N(O)C, R2O, R1(O)CO, R2(O)2SO, R2O(O)CO, (R1)2N(O)CO, (R1)2N, R1(O)C(R1)N, R2(O)2S(R1)N, R2O(O)C(R1)N, (R1)2N(O)C(R1)N, R1O(O)2S(R1)N, (R1)2N(O)2S(R1)N, R2(O)nS, R1O(O)2S, (R1)2N(O)2S, R 1 (O) C (R 1 ) N (O) C, R 2 O (O) C (R 1 ) N (O) C, (R 1 ) 2 N (O) C (R 1 ) N (O ) C, R 2 (O) 2 S (R 1 ) N (O) C, R 1 O (O) 2 S (R 1 ) N (O) C, (R 1 ) 2 N (O) 2 S ( R 1 ) N (O) C, R 2 O, R 1 (O) CO, R 2 (O) 2 SO, R 2 O (O) CO, (R 1 ) 2 N (O) CO, (R 1 ) 2 N, R 1 (O) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N, R 2 O (O) C (R 1 ) N, (R 1 ) 2 N (O ) C (R 1 ) N, R 1 O (O) 2 S (R 1 ) N, (R 1 ) 2 N (O) 2 S (R 1 ) N, R 2 (O) n S, R 1 O (O) 2 S, (R 1 ) 2 N (O) 2 S,
R1(O)C(R1)N(O)2S, R2O(O)C(R1)N(O)2S, (R1)2N(O)C(R1)N(O)2S, (R5O)2(O)P, R1(O)C- (Ci-C6)-Alkyl, R1O(O)C-(Ci-C6)-Alkyl, (R1)2N(O)C-(Ci-C6)-Alkyl, (R1O)(R1)N(O)C-(Ci- C6)-Alkyl, (R1)2N(R1)N(O)C-(Ci-C6)-Alkyl, R1(O)C(R1)N(O)C-(Ci-C6)-Alkyl, R 1 (O) C (R 1 ) N (O) 2 S, R 2 O (O) C (R 1 ) N (O) 2 S, (R 1 ) 2 N (O) C (R 1 ) N (O) 2 S, (R 5 O) 2 (O) P, R 1 (O) C- (C 1 -C 6 ) -alkyl, R 1 O (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) C- (C 1 -C 6 ) -alkyl, (R 1 O) (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, R 1 (O) C (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl,
R2O(O)C(R1)N(O)C-(Ci-C6)-Alkyl, (R1)2N(O)C(R1)N(O)C-(Ci-C6)-Alkyl, R 2 O (O) C (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) C (R 1 ) N (O) C- (Ci-C 6 ) -alkyl,
R2(O)2S(R1)N(O)C-(Ci-C6)-Alkyl, R1O(O)2S(R1)N(O)C-(Ci-C6)-Alkyl, R 2 (O) 2 S (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, R 1 O (O) 2 S (R 1 ) N (O) C- (C 1 -C 6 ) alkyl,
(R1)2N(O)2S(R1)N(O)C-(Ci-C6)-Alkyl, NC-(Ci-C6)-Alkyl, R O-(Ci-C6)-Alkyl, R1(O)CO- (Ci-C6)-Alkyl, R2(0)2SO-(Ci-C6)-Alkyl, R20(0)CO-(Ci-C6)-Alkyl, (R1)2N(0)CO-(Ci-C6)- Alkyl, (R1)2N-(Ci-C6)-Alkyl, R1(0)C(R1)N-(Ci-C6)-Alkyl, R2(0)2S(R1)N-(Ci-C6)-Alkyl, R20(0)C(R1)N-(Ci-C6)-Alkyl, (R1)2N(0)C(R1)N-(Ci-C6)-Alkyl, R10(0)2S(R1)N-(Ci-C6)- Alkyi, (R1)2N(0)2S(R1)N-(Ci-C6)-Alkyl, R2(0)nS-(Ci-C6)-Alky!, R10(0)2S-(Ci-C6)-AlkyS, (R1)2N(0)2S-(Ci-C6)-Alkyl, R1(0)C(R1)N(0)2S-(Ci-C6)-Alkyl, R20(0)C(R1)N(0)2S-(Ci- C6)-Alkyl, (R1)2N(0)C(R1)N(0)2S-(Ci-C6)-Alkyl, (R50)2(0)P-(Ci-C6)-Alkyl, Phenyl, Heteroaryl, Heterocyciyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl- (Ci-CeJ-alkyl, wobei die sechs letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, Cyano, Rhodano, (Ci-CeJ-Alkyl, Halogen-(d- C6)-alkyl, (C3-C6)-Cycloalkyl, R10(0)C, (R1)2N(0)C, R10, (R1)2N, R2(0)nS, R10(0)2S, (R1)2N(0)2S und RO-(Ci-C6)-Alkyl substituiert sind, und wobei Heterocyclyi n (R 1 ) 2 N (O) 2 S (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, NC- (C 1 -C 6 ) -alkyl, R O- (C 1 -C 6 ) Alkyl, R 1 (O) CO- (C 1 -C 6 ) -alkyl, R 2 (O) 2 -SO- (C 1 -C 6 ) -alkyl, R 2 0 (O) CO- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N ( 0) CO- (Ci-C 6) - alkyl, (R 1) 2 N- (Ci-C 6) alkyl, R 1 ((0) C R 1) N- (Ci-C 6) alkyl, R 2 (0) 2 S (R 1 ) N- (C 1 -C 6 ) -alkyl, R 2 0 (0) C (R 1 ) N- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (0) C (R 1 ) N- (C 1 -C 6 ) -alkyl, R 1 0 (0) 2 S (R 1 ) N- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (0 ) 2 S (R 1 ) N- (C 1 -C 6 ) -alkyl, R 2 (O) n S- (C 1 -C 6 ) -alkyl, R 1 0 (0) 2 S- (C 1 -C 6 ) -AlkyS, (R 1 ) 2 N (O) 2 S- (C 1 -C 6 ) -alkyl, R 1 (O) C (R 1 ) N (O) 2 S- (C 1 -C 6 ) -alkyl , R 2 0 (0) C (R 1) N (0) 2 S- (Ci- C6) alkyl, (R 1) 2 N (0) C (R 1) N (0) 2 S- ( C 1 -C 6 ) -alkyl, (R 5 0) 2 (0) P- (C 1 -C 6 ) -alkyl, phenyl, heteroaryl, heterocyclic, phenyl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl ) -alkyl, heterocyclyl- (C 1 -C 12 -alkyl, where the six last-mentioned radicals are in each case represented by s radicals from the group consisting of nitro, halogen, cyano, rhodano, (C 1 -C 6 -alkyl, halogen- (C 1 -C 6 ) alkyl, (C 3 -C 6) -cycloalkyl, R 1 0 (0) C (R 1) 2 N (0) C, R 1 0 (R 1) 2 N, R 2 (0) n S , R 1 0 (0) 2 S, (R 1 ) 2 N (0) 2 S u and RO- (C 1 -C 6 ) alkyl are substituted, and wherein Heterocyclyi n
Oxogruppen trägt, und Q, R, X, W, R1, R2, R3, R4, R5, R6 und R' sowie die Variablen n und s wie in Anspruch 1 definiert sind. And Q, R, X, W, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 'and the variables n and s are as defined in claim 1.
3. N-(Tetrazol-5-yl)-, N-(Triazol-5-yl)-, N-(1 ,2,5-Oxadiazol-3-yl)- und N-(1 ,3,4- Oxadiazol-2-yl)bicycloarylcarbonsäureamide nach Anspruch 1 oder 2, worin 3. N- (tetrazol-5-yl), N- (triazol-5-yl), N- (1, 2,5-oxadiazol-3-yl) - and N- (1, 3,4-) Oxadiazol-2-yl) bicycloarylcarbonsäureamide according to claim 1 or 2, wherein
Q bedeutet einen Rest Q1 , Q2, Q3 oder Q4, Q represents a remainder Q1, Q2, Q3 or Q4,
X bedeutet Nitro, Halogen, Cyano, (Ci-Ce)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)- Alkenyl, (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, R1(0)C, X is nitro, halo, cyano, (Ci-Ce) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) - alkenyl, (C 2 -C 6) -alkynyl, (C 3 -C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, halo (C 3 -C 6) -cycloalkyl (C 1 -C 6) -alkyl, R 1 (0) C,
R1(R1ON=)C, RO(0)C, (R1)2N(0)C, R10, (R1)2N, R1(0)C(R1)N, R2(0)2S(R1)N, R20(0)C(R1)N, (R1)2N(0)C(R1)N, R2(0)nS, R10(0)2S, (R1)2N(0)2S, (R50)2(0)P,R 1 (R 1 ON =) C, RO (O) C, (R 1 ) 2 N (O) C, R 1 O, (R 1 ) 2 N, R 1 (O) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N, R 2 O (0) C (R 1 ) N, (R 1 ) 2 N (O) C (R 1 ) N, R 2 (O) n S, R 1 0 (0) 2 S, (R 1 ) 2 N (O) 2 S, (R 5 0) 2 (0) P,
R1(0)C-(Ci-C6)-Alkyl, R10(0)C-(Ci-C6)-Alkyl, (R1)2N(0)C-(Ci-C6)-Alkyl, NC-(Ci-C6)- Alkyl, RO-(Ci-C6)-Alkyl, (R1)2N-(Ci-C6)-Alkyl, R1(0)C(R1)N-(Ci-C6)-Alkyl, R 1 (0) C- (C 1 -C 6 ) -alkyl, R 1 0 (0) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (0) C- (C 1 -C 6 ) alkyl, NC (Ci-C 6) - alkyl, O- (Ci-C 6) alkyl, (R 1) 2 N- (Ci-C 6) alkyl, R 1 (0) C (R 1 ) N- (C 1 -C 6 ) -alkyl,
R2(0)2S(R1)N-(Ci-C6)-Alkyl, R20(0)C(R1)N-(Ci-C6)-Alkyl, (R1)2N(0)C(R1)N-(Ci-C6)- Alkyl, R2(0)nS-(Ci-C6)-Alkyl, R10(0)2S-(Ci-C6)-Alkyl, (R1)2N(0)2S-(Ci-C6)-Alkyl, (R50)2(0)P-(Ci-C6)-Alkyl, Phenyl, Heteroaryl, Heterocyclyi, Phenyl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, wobei die sechs letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, Cyano, Rhodano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, R10, (R1)2N, R2(0)„S, RO(0)2S, (R1 )2N(0)2S und R10-(Ci-C6)-Alkyl substituiert sind und wobei Heterocyclyl n R 2 (0) 2 S (R 1 ) N- (C 1 -C 6 ) -alkyl, R 2 0 (0) C (R 1 ) N- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (0) C (R 1) N- (Ci-C 6) - alkyl, R 2 (0) n S- (Ci-C 6) alkyl, R 1 0 (0) 2 S- (Ci-C 6 ) Alkyl, (R 1 ) 2 N (O) 2 S- (C 1 -C 6 ) -alkyl, (R 5 0) 2 (O) P- (C 1 -C 6 ) -alkyl, phenyl, heteroaryl, heterocyclic , Phenyl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, where the six last-mentioned radicals are in each case represented by s radicals from the group consisting of nitro, halogen, Cyano, rhodano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, R 1 0, (R 1 ) 2 N, R 2 (0) "S, RO (0) 2 S, (R 1 ) 2 N (O) 2 S and R 1 are 0- (C 1 -C 6 ) -alkyl substituted and wherein Heterocyclyl n
Oxogruppen trägt, Wearing oxo groups,
W bedeutet Wasserstoff, Halogen, Nitro, Cyano, (Ci-CeJ-Alkyl, Halogen-(Ci-Ce)- alkyl, (C3-C/)-Cycloalkyl, (Ci-C6)-Alkoxy, (Ci-C6)-Alkyl-(0)nS-, R10(0)C, (R1 )2N, R1(0)C(R1 )N oder R2(0)2S(R1 )N, W is hydrogen, halogen, nitro, cyano, (C 1 -C 6 -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 4 -alkyl) 6 ) -alkyl- (0) n S-, R 1 O (0) C, (R 1 ) 2 N, R 1 (O) C (R 1 ) N or R 2 (O) 2 S (R 1 ) N,
R bedeutet Wasserstoff, Rx bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2- Ce)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, wobei die sechs vorstehend genannten Reste jeweils durch s Reste aus der Gruppe bestehend aus R2(0)nS, (R1 )2N, RO, R1(0)C, RO(0)C, R1(0)CO, R20(0)CO, R1(O)C(R1 )N, R2(0)2S(R1 )N, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocyclyl und Phenyl substituiert sind, wobei die vier letztgenannten Reste durch s Reste aus der Gruppe bestehend aus (Ci-C6)-Alkyl, Halogen-(Ci-C-6)-alkyl, (Ci-C-6)-Alkoxy und Halogen substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, oder Rx bedeutet (C3-C/)-Cycloalkyl, wobei dieser Rest durch s Reste aus der Gruppe bestehend aus Halogen, (Ci-Ce)-Alkyl und Halogen-(Ci-Ce)-alkyl substituiert ist, R is hydrogen, R x represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 - Ce) alkenyl, (C C 2 -C 6) -alkynyl, halogeno (C 3 -C 6) -alkynyl, where the six radicals mentioned above are each represented by s radicals selected from the group consisting of R 2 (O) n S, (R 1 ) 2 N, RO, R 1 (0) C, RO (0) C, R 1 (0) CO, R 2 0 (0) CO, R 1 (O) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N, (C3-C6) -cycloalkyl, heteroaryl, heterocyclyl and phenyl are substituted, wherein the four latter radicals by s radicals from the group consisting of (Ci-C6) -alkyl, halogeno (Ci-C-6) -alkyl , (Ci-C-6) -alkoxy and halogen, and wherein heterocyclyl n carries oxo groups, or R x is (C3-C /) - cycloalkyl, this radical being represented by s radicals selected from the group consisting of halogen, (Ci -Ce) -alkyl and halogen- (Ci-Ce) -alkyl,
RY bedeutet Wasserstoff, (Ci-Ce)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C/)-Cycloalkyl, (Ci-CeJ-Alkoxy, Methoxycarbonyl, Methoxycarbonylmethyl, Halogen, Amino, R Y is hydrogen, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 1 -C 6 -alkoxy, methoxycarbonyl, methoxycarbonylmethyl, halogen, amino,
Aminocarbonyl oder Methoxymethyl, Aminocarbonyl or methoxymethyl,
Rz bedeutet Wasserstoff, (Ci-C6)-Alkyl, RO-(Ci-C6)-Alkyl, R'CH2, (C3-C/)- Cycloalkyl, Halogen-(Ci-C6)-alkyl, R1O, R1(H)N, Methoxycarbonyl, Acetylamino oder Methylsulfonyl, R1 bedeutet Wasserstoff, (Ci-Ce)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-O-(Ci-C6)- alkyl, Cycloalkyl-(Ci-C6)-alkyl-O-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, Phenyl-O-(Ci-C6)- alkyl, Heteroaryl-O-(Ci-C6)-alkyl, Heterocyclyl-O-(Ci-C6)-alkyl, wobei die neun letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, R30(0)C, (R3)2N(0)C, R30, (R3)2N, R4(0)nS und R30-(Ci-Ce)-Alkyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R z represents hydrogen, (Ci-C 6) -alkyl, O- (Ci-C 6) -alkyl, R'CH 2, (C 3 -C /) - cycloalkyl, halo- (Ci-C6) alkyl, R 1 O, R 1 (H) N, methoxycarbonyl, acetylamino or methylsulfonyl, R 1 represents hydrogen, (Ci-Ce) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl , halo (C3-C6) cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (Ci-C 6) alkyl-O- (Ci-C 6) - alkyl, Cycloalkyl- (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl, Heterocyclyl (C 1 -C 6 ) -alkyl, phenyl-O- (C 1 -C 6 ) -alkyl, heteroaryl-O- (C 1 -C 6 ) -alkyl, heterocyclyl-O- (C 1 -C 6) -alkyl, where the nine the last-mentioned radicals in each case by s radicals from the group consisting of nitro, halogen, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, R 3 0 (O) C, (R 3 ) 2 N ( 0) C, R 3 O, (R 3 ) 2 N, R 4 (O) n S and R 3 are 0- (C 1 -C 6) -alkyl, and wherein heterocyclyl carries n oxo groups,
R2 bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, Halogen-(C3- C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-0-(Ci-C6)-alkyl, R 2 is (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) cycloalkyl, halo (C 3 - C 6) cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl,
Cycloalkyl-(Ci-C6)-alkyl-0-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, Phenyl-0-(Ci-C6)- alkyl, Heteroaryl-0-(Ci-C6)-alkyl, Heterocyclyl-0-(Ci-C6)-alkyl, wobei die neun letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, R30(0)C, (R3)2N(0)C, R30, (R3)2N, R4(0)nS und R30-(Ci-Ce)-Alkyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Cycloalkyl- (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl, Heterocyclyl- (C 1 -C 6 ) -alkyl, phenyl-0- (C 1 -C 6 ) -alkyl, heteroaryl-0- (C 1 -C 6 ) -alkyl, heterocyclyl-0- (C 1 -C 6) -alkyl, where the nine latter radicals in each case by s radicals from the group consisting of nitro, halogen, (Ci-C 6 ) alkyl, halogeno (Ci-C 6 ) alkyl, R 3 0 (0) C, (R 3 ) 2 N (0) C, R 3 O, (R 3 ) 2 N, R 4 (O) n S and R 3 are 0- (C 1 -C 6) -alkyl, and wherein heterocyclyl carries n oxo groups,
R3 bedeutet Wasserstoff oder (Ci-Ce)-Alkyl, R4 bedeutet (Ci-C6)-Alkyl, R5 bedeutet Wasserstoff oder (Ci-C4)-Alkyl, R 3 is hydrogen or (C 1 -C 6 ) -alkyl, R 4 is (C 1 -C 6 ) -alkyl, R 5 is hydrogen or (C 1 -C 4 ) -alkyl,
R' bedeutet Acetoxy, Acetamido, Methoxycarbonyl oder (C3-C6)-Cycloalkyl, n bedeutet 0, 1 oder 2, s bedeutet 0, 1 , 2 oder 3, R 'is acetoxy, acetamido, methoxycarbonyl or (C 3 -C 6) -cycloalkyl, n is 0, 1 or 2, s is 0, 1, 2 or 3,
L bedeutet eine Brücke ausgewählt aus der Gruppe bestehend aus A1 , A2, A3,L means a bridge selected from the group consisting of A1, A2, A3,
A4, A5, A6, A7, A8, A9, A10, A1 1 , A12, A13, A14, A17, A25, A26, A27, A28, A29, A30, A31 , A32, A33, A34, A35, A36, A37, A38, A41 , A49, A50, A51 , A53, A55, A57, A59, A61 , A62, A72, A139, A140, A141 , A142, A143, A144, A145, A146, A147, A148, A149, A150, A151 , A157, A158, A168, A274, A275, A276, A277, A278, A279, A280, A281 , A282, A283, A284, A285, A286, A287, A363, A364, A365, A366, A367, A368, A369, A370, A371 , A372 und A373, R7, R8, R12, R13, R22 und R23 bedeuten unabhängig voneinander jeweils A4, A5, A6, A7, A8, A9, A10, A1, A12, A13, A14, A17, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, A36, A37 , A38, A41, A49, A50, A51, A53, A55, A57, A59, A61, A62, A72, A139, A140, A141, A142, A143, A144, A145, A146, A147, A148, A149, A150, A151 , A157, A158, A168, A274, A275, A276, A277, A278, A279, A280, A281, A282, A283, A284, A285, A286, A287, A363, A364, A365, A366, A367, A368, A369, A370 , A371, A372 and A373, R 7 , R 8 , R 12 , R 13 , R 22 and R 23 are each independently
Wasserstoff, Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, Hydrogen, halogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl,
Halogen-(C3-C6)-cycloalkyl, R1(0)C, R1(R1ON=)C, R10(0)C, (R1 )2N(0)C, R20, R1(0)CO, (R1 )2N, R1(0)C(R1)N, R2(0)nS, R10-(Ci-C6)-Aikyl oder R2(0)nS-(Ci-C6)- AlkyS, Halo (C 3 -C 6) cycloalkyl, R 1 (0) C, R 1 (R 1 ON =) C, R 1 0 (0) C (R 1) 2 N (0) C, R 2 0, R 1 (0) CO, (R 1 ) 2 N, R 1 (O) C (R 1 ) N, R 2 (O) n S, R 1 0- (Ci-C 6 ) -Aikyl or R 2 (0) n S- (Ci-C 6 ) - AlkyS,
R9, R10, R14, R15, R16, R17, R20, R21 , R24 und R25 bedeuten unabhängig voneinander jeweils Wasserstoff, Halogen, (Ci-C4)-Alkyl, (Ci-C4)-Halogenalkyl oder (Ci-C4)-Alkoxy, oder je zwei geminale R9, R10, R14, R15, R16, R17, R20, R21 , R24 und R25 bilden gemeinsam mit dem Kohlenstoffatom, an das sie gebunden sind, eine Carbonylgruppe oder ein Oxim der Formel C=NOR1 oder je zwei geminale R9, R10, R14, R15, R16, R17, R20, R21 , R24 und R25 bedeuten ein Acetal der Formel -0-(C2-C4)-Alkylen-0-, R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 are each independently hydrogen, halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) Haloalkyl or (C 1 -C 4) -alkoxy, or in each case two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 form together with the carbon atom, to which they are attached, a carbonyl group or an oxime of the formula C =NOR 1 or in each case two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 an acetal of the formula denotes -O- (C 2 -C 4 ) -alkylene-0-,
R1 1 , R18, R19, R26 und R27 bedeuten unabhängig voneinander jeweils Wasserstoff oder (Ci-C6)-Alkyl, wobei die (Ci-C6)-Alkylgruppe durch s Reste aus der Gruppe R 1 1 , R 18 , R 19 , R 26 and R 27 are each independently hydrogen or (Ci-C6) alkyl, wherein the (Ci-C6) alkyl group by s radicals from the group
bestehend aus R2(0)nS, (R1 )2N, R10, R1(0)C, R10(0)C, R1(0)CO, R20(0)CO, R1(0)C(R1 )N, R2(0)2S(R1 )N, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocyclyi und Phenyl substituiert sind, wobei die vier letztgenannten Reste durch s Reste aus der Gruppe bestehend aus (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-Ce)- alkoxy und Halogen substituiert sind, und wobei Heterocyclyi n Oxogruppen trägt, oder R1 1 , R18, R19, R26 und R27 bedeuten unabhängig voneinander jeweils (C3-C/)- Cycloalkyl, Heteroaryl, Heterocyclyi oder Phenyl, wobei die vier vorstehend genannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, (C-i-Ce)- Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (Ci-C6)-Alkyl- S(0),„ (Ci-C6)-Alkoxy, Halogen-(Ci-Ce)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C4)-alkyl substituiert sind, consisting of R 2 (0) n S, (R 1) 2 N, R 1 is 0, R 1 (0) C, R 1 0 (0) C, R 1 (0) CO, R 2 0 (0) CO , R 1 (O) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N, (C 3 -C 6 ) -cycloalkyl, heteroaryl, heterocyclyl and phenyl are substituted, wherein the four latter radicals by s radicals from the group consisting of (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and halogen are substituted, and wherein heterocyclyl n carries oxo groups, or R 1 1 , R 18 , R 19 , R 26 and R 27 are each independently (C 3 -C /) - cycloalkyl, heteroaryl, heterocyclyl or phenyl, wherein the four radicals mentioned above in each case by s radicals selected from the group consisting of halogen, nitro, (Ci-Ce) - alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 6) alkyl S (0), (C 1 -C 6 ) -alkoxy, halogen- (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -alkyl are substituted,
R28, R29, R30 und R31 bedeuten unabhängig voneinander jeweils Wasserstoff, Nitro, Halogen, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, Halogen-(C3- C6)-cyc!oalkyl, R1(O)C, R1(R1ON=)C, R1O(O)C, (R1)2N(O)C, R2O, R1(O)CO, (R1 )2N, R1(O)C(R1)N, R2(O)nS, R1O(O)2S, R1(O)C-(Ci-C6)-Alkyl, R1O(O)C-(Ci-C6)-Alkyl, (R1)2N(O)C-(Ci-C6)-Alkyl, NC-(Ci-C6)-Aikyl, R1O-(Ci-C6)-Alkyl, R1(O)CO-(Ci-C6)-Alkyl, (R1 )2N-(Ci-C6)-Alkyl, R1(O)C(R1 )N-(Ci-C6)-Alkyl, R2(O)nS-(Ci-C6)-Alkyl, Phenyl, Heteroaryl, Heterocyclyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl- (Ci-C6)-alkyl, wobei die sechs letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Nitro, Halogen, Cyano, (Ci-C-6)-Alkyl, Halogen-(Ci-C-6)-alkyl, (C3-C6)-Cycloalkyl, R1O(O)C, (R1)2N(O)C, RO, (R1)2N, R2(O)nS, R1O(O)2S, R 28, R 29, R 30 and R 31 are each independently hydrogen, nitro, halogen, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -Cycloalkyl, halogen- (C 3 - C 6 ) -cycloalkyl, R 1 (O) C, R 1 (R 1 ON =) C, R 1 O (O) C, (R 1 ) 2 N (O) C, R 2 O, R 1 (O) CO, (R 1 ) 2 N, R 1 (O) C (R 1 ) N, R 2 (O) n S, R 1 O (O) 2 S, R 1 (O) C- (Ci -C 6) alkyl, R 1 O (O) C- (Ci-C 6) -alkyl, (R 1) 2 N (O) C- (Ci-C 6) -alkyl, NC (Ci-C 6 ) -alkyl, R 1 O- (C 1 -C 6 ) -alkyl, R 1 (O) CO- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N- (C 1 -C 6 ) -alkyl, R 1 (O) C (R 1 ) N- (C 1 -C 6 ) -alkyl, R 2 (O) nS- (C 1 -C 6 ) -alkyl, phenyl, heteroaryl, heterocyclyl, phenyl (C 1 -C 6 ) alkyl, heteroaryl- (C 1 -C 6) -alkyl, heterocyclyl- (C 1 -C 6) -alkyl, where the six last-mentioned radicals are in each case represented by s radicals from the group consisting of nitro, halogen, cyano, (C 1 -C 6) Alkyl, halo (C 1 -C 6) alkyl, (C 3 -C 6 ) cycloalkyl, R 1 O (O) C, (R 1 ) 2 N (O) C, RO, (R 1 ) N 2, R 2 (O) n S, R 1 O (O) 2 S,
(R1 )2N(O)2S und R1O-(Ci-C6)-Alkyl substituiert sind, und wobei Heterocyclyl n (R 1 ) 2 N (O) 2 S and R 1 O- (C 1 -C 6 ) -alkyl, and wherein heterocyclyl n
Oxogruppen trägt. Carries oxo groups.
4. N-(Tetrazol-5-yl)-, N-(Triazol-5-yl)-, N-(1 ,2,5-Oxadiazol-3-yl)- und N-(1 ,3,4- Oxadiazol-2-yl)bicycloarylcarbonsäureamide nach einem der Ansprüche 1 bis 3, worin Q bedeutet einen Rest Q1 , Q2, Q3 oder Q4, 4. N- (tetrazol-5-yl), N- (triazol-5-yl), N- (1, 2,5-oxadiazol-3-yl) - and N- (1, 3,4-) Oxadiazol-2-yl) bicycloarylcarboxamides according to one of Claims 1 to 3, in which Q denotes a group Q1, Q2, Q3 or Q4,
X bedeutet Nitro, Halogen, Methyl, Ethyl, n-Propyl, iso-Propyl, Trifluormethyl, Difluormethyl, Chlordifluormethyl, Dichlorfluormethyl, Trichlormethyl, Pentafluorethyl, Heptafluorisopropyl, Cyclopropyl, Methoxy, Ethoxy, Methylsulfanyl, Methylsulfinyl, Methylsulfonyl, Methoxymethyl, Ethoxymethyl, Methoxyethyl, Methoxyethoxymethyl, Methylthiomethyl, Methylsulfinylmethyl oder Methylsulfonylmethyl, X is nitro, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, heptafluoroisopropyl, cyclopropyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, Methoxyethoxymethyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl,
W bedeutet Wasserstoff, Chlor oder Methyl, W is hydrogen, chlorine or methyl,
R bedeutet Wasserstoff, R is hydrogen,
Rx bedeutet Methyl, Ethyl, n-Propyl, Prop-2-en-1 -yl, Methoxyethyl, Ethoxyethyl oder Methoxyethoxyethyl, R x represents methyl, ethyl, n-propyl, prop-2-en-1-yl, methoxyethyl, ethoxyethyl or methoxyethoxyethyl,
RY bedeutet Methyl, Ethyl, n-Propyl, Chlor oder Amino, R Y is methyl, ethyl, n-propyl, chlorine or amino,
Rz bedeutet Methyl, Ethyl, n-Propyl oder Methoxymethyl. R z is methyl, ethyl, n-propyl or methoxymethyl.
L bedeutet eine Brücke ausgewählt aus der Gruppe bestehend aus A1 , A2, A4,L means a bridge selected from the group consisting of A1, A2, A4,
A5, A6, A7, A8, A25, A26, A28, A29, A30, A31 , A32, A49, A50, A51 , A53, A55, A57, A59, A61 , A 39, A140, A141 , A142, A143, A145, A 46, A147, A148, A 49, A 50,A5, A6, A7, A8, A25, A26, A28, A29, A30, A31, A32, A49, A50, A51, A53, A55, A57, A59, A61, A39, A140, A141, A142, A143, A145, A46, A147, A148, A49, A50,
A274, A275, A278, A279, A280, A281 , A282, A283, A284, A285, A286, A363, A364, A365, A366, A367, A368, A369, A370, A371 , A372 und A373, 7, R8, R12, R13, R22 und R23 bedeuten unabhängig voneinander jeweils A274, A275, A278, A279, A280, A281, A282, A283, A284, A285, A286, A363, A364, A365, A366, A367, A368, A369, A370, A371, A372 and A373, 7, R 8 , R 12 , R 13 , R 22 and R 23 are each independently
Wasserstoff, Halogen, Methyl, Ethyl, n-Propyl, iso-Propyl, Trifiuormethyl, Cyclopropyi, Methoxy, Ethoxy, Methylsulfanyl, Methylsulfinyl, Methyisulfonyl, Methoxymethyl, Ethoxymethyl, Methoxyethyl, Methoxyethoxymethyl, Methylthiomethyl,  Is hydrogen, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, cyclopropyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxyethoxymethyl, methylthiomethyl,
Methylsulfinylmethyl oder Methylsulfonylmethyl, Methylsulfinylmethyl or methylsulfonylmethyl,
R9, R10, R14, R15, R16, R17, R20, R21, R24 und R25 bedeuten unabhängig voneinander jeweils Wasserstoff, Halogen, Methyl, Methoxy, Ethoxy oder je zwei geminale R9, R10, R14, R15, R16, R17, R20, R21, R24 und R25 bilden gemeinsam mit dem Kohlenstoffatom, an das sie gebunden sind, eine Carbonylgruppe oder einR 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 are each independently hydrogen, halogen, methyl, methoxy, ethoxy or two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 together with the carbon atom to which they are attached form a carbonyl group or a
Oxim der Formel C=NOR1 oder je zwei geminale R9, R10, R14, R15, R16, R17, R20, R21, R24 und R25 bedeuten ein Acetal der Formel -0-(CH2)2-0-, Oxime of formula C = NOR 1 or two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 is an acetal of the formula -0- (CH 2 ) 2-0-,
R1 bedeutet Wasserstoff, Methyl oder Ethyl, R 1 is hydrogen, methyl or ethyl,
R11, R19, R26 und R27 bedeuten unabhängig voneinander jeweils Wasserstoff oder Methyl, R 11 , R 19 , R 26 and R 27 are each independently hydrogen or methyl,
R28, R29, R30 und R31 bedeuten unabhängig voneinander jeweils Wasserstoff, Nitro, Halogen, Methyl, Ethyl, n-Propyl, iso-Propyl, Trifiuormethyl, Difluormethyl, R 28 , R 29 , R 30 and R 31 independently of one another are each hydrogen, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl,
Chlordifluormethyl, Dichlorfluormethyl, Trichlormethyl, Pentafluorethyl, Chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl,
Heptafluorisopropyl, Cyclopropyi, Methoxy, Ethoxy, Methylsulfanyl, Methylsulfinyl, Methyisulfonyl, Methoxymethyl, Ethoxymethyl, Methoxyethyl, Methoxyethoxymethyl, Methylthiomethyl, Methylsulfinylmethyl oder Methylsulfonylmethyl. Heptafluoroisopropyl, cyclopropyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxyethoxymethyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl.
5. Herbizide Mittel, gekennzeichne t durch einen herbizid wirksamen Gehalt an mindestens einer Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 4. 5. Herbicides, marked t by a herbicidally active content of at least one compound of the formula (I) according to one of claims 1 to 4.
6. Herbizide Mittel nach Anspruch 5 in Mischung mit Formulierungshilfsmitteln. 6. A herbicidal composition according to claim 5 in admixture with formulation auxiliaries.
7. Herbizide Mittel nach Anspruch 5 oder 6 enthaltend mindestens einen weiteren Pestizid wirksamen Stoff aus der Gruppe Insektizide, Akarizide, Herbizide, Fungizide, Safener und Wachstumsregulatoren. 7. A herbicidal composition according to claim 5 or 6 containing at least one further pesticide active substance from the group of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.
8. Herbizide Mittel nach Anspruch 7 enthaltend einen Safener. 8. A herbicidal composition according to claim 7 containing a safener.
9. Herbizide Mittel nach Anspruch 8 enthaltend cyprosulfamid, cloquintocet-mexyl, mefenpyr-diethyl oder isoxadifen-ethyl. 9. A herbicidal composition according to claim 8 containing cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.
10. Herbizide Mittel nach einem der Ansprüche 7 bis 9 enthaltend ein weiteres Herbizid. 10. A herbicidal composition according to any one of claims 7 to 9 containing a further herbicide.
1 1 . Verfahren zur Bekämpfung unerwünschter Pflanzen, dadurch gekennzeichnet, daß man eine wirksame Menge mindestens einer Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 4 oder eines herbiziden Mittels nach einem der Ansprüche 5 bis 10 auf die Pflanzen oder auf den Ort des unerwünschten Pflanzenwachstums appliziert. 1 1. A method for controlling undesirable plants, characterized in that an effective amount of at least one compound of the formula (I) according to one of Claims 1 to 4 or of a herbicidal composition according to one of Claims 5 to 10 is applied to the plants or to the site of undesired plant growth applied.
12. Verwendung von Verbindungen der Formel (I) gemäß einem der Ansprüche 1 bis 4 oder von herbiziden Mitteln nach einem der Ansprüche 5 bis 10 zur Bekämpfung unerwünschter Pflanzen. 12. Use of compounds of the formula (I) according to any one of claims 1 to 4 or of herbicidal compositions according to any one of claims 5 to 10 for controlling unwanted plants.
13. Verwendung nach Anspruch 12, dadurch gekennzeichnet, daß die 13. Use according to claim 12, characterized in that the
Verbindungen der Formel (I) zur Bekämpfung unerwünschter Pflanzen in Kulturen von Nutzpflanzen eingesetzt werden. Compounds of formula (I) for controlling undesirable plants in crops of crops are used.
14. Verwendung nach Anspruch 13, dadurch gekennzeichnet, daß die Nutzpflanzen transgene Nutzpflanzen sind. 14. Use according to claim 13, characterized in that the crops are transgenic crops.
EP13756174.2A 2012-09-05 2013-09-03 Herbicidally active bicycloaryl carboxylic acid amides Withdrawn EP2892885A1 (en)

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