WO2015007633A1 - 6-azinone-2-carbonyl derivatives and their use as herbicides - Google Patents

6-azinone-2-carbonyl derivatives and their use as herbicides Download PDF

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WO2015007633A1
WO2015007633A1 PCT/EP2014/064897 EP2014064897W WO2015007633A1 WO 2015007633 A1 WO2015007633 A1 WO 2015007633A1 EP 2014064897 W EP2014064897 W EP 2014064897W WO 2015007633 A1 WO2015007633 A1 WO 2015007633A1
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alkyl
halogen
cycloalkyl
alkoxy
heterocyclyl
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PCT/EP2014/064897
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German (de)
French (fr)
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Ralf Braun
Christian Waldraff
Jörg Tiebes
Hansjörg Dietrich
Dirk Schmutzler
Elmar Gatzweiler
Christopher Hugh Rosinger
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Bayer Cropscience Ag
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Publication of WO2015007633A1 publication Critical patent/WO2015007633A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
    • C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • 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

Definitions

  • the invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and weeds in
  • WO2012 / 039141 A1 describes 6-pyridone-2-carbonylcyclohexanediones and 6-pyridone-2-carbonyl-pyrazoles as herbicides. From the priority senior, not
  • 6-azino-2-carbonyl derivatives of the invention are dissolved.
  • An object of the present invention are thus 6-azino-2-carbonyl derivatives of the formula (I) or salts thereof
  • Q is a radical Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , Q 7 or Q 8 ,
  • R 3 is (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, where these radicals are each represented by s radicals from the group consisting of halogen, cyano, hydroxyl, nitro, SiR 10 3, PO (OR 10) 2, S (O) n - (Ci-C 6) -alkyl, (Ci-C 6) alkoxy, halo (Ci-C 6) alkoxy, COR 3a , COOR 3a , OCOR 3a , NR 3a COR 3a , NR 3a SO 2 R 3b , (C 3 -C 6 ) cycloalkyl, heteroaryl, heterocyclyl or phenyl are substituted, wherein the 4 latter radicals each by p radicals from the group from methyl, ethyl, methoxy, trifluoromethyl, cyano and
  • R 3 means by p radicals from the group consisting of halogen, nitro, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, S (O ) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -alkyl-substituted phenyl,
  • R 3a is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl or (C 3 -C 6 ) - Cycloalkyl- (C 1 -C 6) -alkyl or phenyl,
  • R 3b represents (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl or (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl or (C3-C6 ) Cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
  • R 4 represents hydrogen, (Ci-C 6) -alkyl, (C 3 -C 7) -cycloalkyl, halo (Ci-C 6) alkyl, (Ci-Ce) alkoxy, halo (Ci- C 6) alkoxy, (C 2 -C 6) -alkenyl, (C 2 -C 6) alkenyloxy, (C 2 -C 6) - haloalkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) alkynyloxy, (C 2 -C 6) haloalkynyl, (Ci-C6) - alkoxy- (Ci-C6) alkyl, cyano-, nitro-, methylsulphenyl, methylsulphinyl, methylsulphonyl, Acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl,
  • R 5 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, CH 2 R 5a, (C 3 - C 7) cycloalkyl, halo ( Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C2-C6) alkenyl, (C2 - Ce) alkynyl, halo (C2-C6) alkynyl, OR 6, NHR 6 , methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methylcarbonyl,
  • Trifluoromethylcarbonyl dimethylamino, acetylamino, methylsulfenyl, methylsulfinyl, methylsulfonyl or in each case by p radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 4 ) -alkyl C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- Ci-C) -alkyl
  • R 5a represents acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl,
  • Methylaminocarbonyl dimethylaminocarbonyl, (C 1 -C 6) -alkoxy, (C 3 -C 6) -cycloalkyl or in each case by p radicals from the group consisting of methyl, ethyl, methoxy,
  • W is O, CO or CR c6 R c7 ,
  • R c1 is hydroxy or SR 11 ,
  • R c2 and R c5 are each independently hydrogen or (Ci-C 4 ) - alkyl, or
  • R c2 and R c5 together form an ethylene or vinylene group
  • R c3 , R c4 , R c6 and R c7 are each independently hydrogen or (C 1 -C 4 ) -alkyl
  • RP 1 is hydrogen, (Ci-C 6 ) alkylsulfonyl, (Ci-C) alkoxy- (Ci-C 6 ) - alkylsulfonyl, or in each case by m identical or different radicals from the group consisting of halogen, (Ci-C 4 ) -alkyl and (C 1 -C 4 ) -alkoxy substituted
  • R p2 is (C 1 -C 4 ) -alkyl
  • RP 3 is hydrogen, (C 1 -C 4) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 1 -C 4) -alkyl (C 3 -C 8 ) -cycloalkyl, (C 3 -C 6 ) -halocycloalkyl,
  • R n1 represents (C 1 -C 4) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 1 -C 4) -alkyl (C 3 -C 8 ) -cycloalkyl, (C 3 -C 6 ) -halocycloalkyl
  • R n2 is hydrogen, CO 2 (C 1 -C 6 ) -alkyl or S (O) n (C 1 -C 6 ) -alkyl,
  • X 1 is N or CR 2 ,
  • X 2 is N or CH
  • R 2 is hydrogen, halogen, cyano, nitro, (Ci-C) alkyl, (Ci-C) -haloalkyl, (C2-C6) alkenyl, (C2-C6) haloalkenyl, (C2-C6 ) alkynyl, (C2-C6) -haloalkynyl, (C3 - C6) cycloalkyl, (C 3 -C 6) halocycloalkyl, (Ci-C6) alkyl-O- (Ci-C 6) - alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, (Ci-C) alkoxy or (Ci-C) haloalkoxy,
  • Y represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C 2 -C 6) - alkenyl, (C2-C6) - alkynyl, halo (C 3 -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, OCOOR 6 , OC (O) N (R 6 ) 2 , OR 6 , OCOR 6 , OSO 2 R 7 , ( C 1 -C 6 ) -alkyl-S (O) n R 7 , (C 1
  • Oxo groups, or Z and R 2 form together with the two carbon atoms to which they are attached, a five- or six-membered ring consisting of t
  • R 6 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 - C 6) haloalkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 - C 6) cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O - (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-Ce) - alkyl heteroaryl, Heterocycl, (Ci-C 6) alkyl-heterocycl
  • R 9 is (Ci-C 6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl or phenyl, R 10 is (Ci-C 4) -alkyl,
  • R 11 is (C 1 -C 4 ) -alkyl or by p radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkoxy and (C 1 -C 4) -alkyl C) haloalkoxy-substituted phenyl, n is 0, 1 or 2, p is 0, 1, 2 or 3, q is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is e 1, 2, 3, 4, 5 or 6.
  • alkyl radicals having more than two carbon atoms may be straight-chain or branched.
  • Alkyl radicals are, for example, 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 is for example 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 fused 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-tri
  • the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetric carbon atoms are present, then enantiomers and
  • Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods. Likewise, stereoisomers can be prepared by using stereoselective reactions using optically active starting materials and / or
  • 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.
  • R 3 represents (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, where these radicals in each case by s radicals selected from the group consisting of halogen, cyano, nitro, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 3 -C 6 ) -cycloalkyl , Heteroaryl, heterocyclic or phenyl, wherein the 4 last-mentioned radicals are each substituted by p radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and wherein heterocyclyl n carries oxo groups, or R 3 is replaced by p radicals from the group
  • R 5 represents hydrogen, (Ci-C 6) -alkyl, (C 3 -C 7) cycloalkyl, halo (Ci-C 6) alkyl, (C3-C7) cycloalkylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,
  • W is O, CO or CR c6 R c7 ,
  • R c1 is hydroxy
  • R c2 and R c5 are each independently hydrogen or methyl, or R c2 and R c5 together form an ethylene or vinylene group,
  • R c3 , R c4 , R c6 and R c7 are each independently hydrogen or methyl
  • R p1 is hydrogen
  • RP 2 is (C 1 -C 4 ) -alkyl
  • R p3 is hydrogen, (C 1 -C 4) -alkyl or cyclopropyl,
  • R n1 is cycloproyl
  • R n2 is hydrogen
  • X 1 is N or CR 2 ,
  • X 2 is N or CH
  • R 2 is hydrogen, halogen, (Ci-C) alkyl, (Ci-C) -haloalkyl, (C 2 -C 6) - alkenyl, (C2-C6) -alkynyl, (C3-C6) cycloalkyl , (Ci-C6) alkyl-O- (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, (Ci-C) alkoxy or (Ci- C) haloalkoxy, Y represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C 2 -C 6) - alkenyl, (C2-C6) - alkynyl, halo (C3-C6) -alkynyl, (C3-C6) -cycloalkyl, halo- (
  • Z is hydrogen, halogen, cyano, thiocyanato, nitro, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, halo (C 2 - C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (Cs-CeJ- CycloalkyKCi-Ce) -alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 6 , COOR 6 , OCOOR 6 , NR 6 COOR 6 , C (O) N (R 6 ) 2 , NR 6 C (O) N (R 6 ) 2 , OC (O)
  • Heterocyclyl carries n oxo groups
  • R 7 is (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl, (C 3 - C 6 ) -cycloalkenyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl heterocycly
  • R 8 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) cycloalkyl (Ci-C 6) alkyl or phenyl,
  • R 9 is (Ci-C 6) -alkyl, represents (C 2 -C 6) -alkenyl, (C 2 -C 6) alkynyl or phenyl,
  • R 10 is (C 1 -C 4 ) -alkyl, n is 0, 1 or 2,
  • P is 0, 1, 2 or 3
  • q is 0, 1, 2, 3 or 4
  • s is 0, 1, 2, 3, 4 or 5
  • t is e 1, 2, 3, 4, 5 or 6.
  • Q denotes a radical Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , Q 7 or Q 8 ,
  • R 3 is in each case by s radicals from the group consisting of halogen, cyano, nitro, S (O) n- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy and halogen (C 1 -C 6 ) alkoxy-substituted (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl or (C 2 -C 8 ) -alkynyl,
  • R 4 is (Ci-C 6) -alkyl, (C 3 -C 7) -cycloalkyl, halo (Ci-C 6) alkyl, (Ci-C 6) - alkoxy, halo (Ci-C6 ) -alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl,
  • Trifluoromethylcarbonyl halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, 1, 2,4-triazole-1H, 1-pyrazole-1H, 2-thiophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1, 2,4-oxadiazol-3-yl, benzoxazol-2-yl,
  • R 5 represents Wassetrstoff, (Ci-C 6) -alkyl, (C 3 -C 7) cycloalkyl, halo (Ci-C 6) alkyl, (C3-C7) cycloalkylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,
  • W is O, CO or CR c6 R c7 ,
  • R c1 is hydroxy
  • R c2 and R c5 are each independently hydrogen or methyl, or R c2 and R c5 together form an ethylene or vinylene group,
  • R c3 , R c4 , R c6 and R c7 are each independently hydrogen or methyl
  • R p1 is hydrogen
  • RP 2 is (C 1 -C 4 ) -alkyl
  • R p3 is hydrogen, (C 1 -C 4) -alkyl or cyclopropyl,
  • R n1 is cycloproyl
  • R n2 is hydrogen
  • X 1 is N or CR 2 ,
  • X 2 is N or CH
  • R 2 is hydrogen, halogen, (C 1 -C 4) -alkyl
  • Y represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C3-C6) cycloalkyl, OR 6, S (O) n R 7, (Ci-C 6) alkyl -S (O) n R 7 , (C 1 -C 6 ) -alkyl-OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N ( R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 6 SO 2 R 7 , (C 1 -C 6 ) -alkyl heteroaryl, (C 1 -C 6 ) -Alkyl-heterocyclyl, where the
  • Z is hydrogen, halogen, cyano, thiocyanato, nitro, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, halo (C 2 - C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (Cs-CeJ- CycloalkyKCi-Ce) -alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 6 , COOR 6 , OCOOR 6 , NR 6 COOR 6 , C (O) N (R 6 ) 2 , NR 6 C (O) N (R 6 ) 2 , OC (O)
  • Heterocyclyl carries n oxo groups
  • R 7 is (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl, (C 3 - C 6 ) -cycloalkenyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl heterocycly
  • R 8 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) cycloalkyl (Ci-C 6) alkyl or phenyl,
  • R 9 is (Ci-C 6) -alkyl, represents (C 2 -C 6) -alkenyl, (C 2 -C 6) alkynyl or phenyl,
  • R 10 is (C 1 -C 4 ) -alkyl, n is 0, 1 or 2,
  • azin-2-one-6-carboxylic acid chlorides (II) or their underlying azin-2-one-6-carboxylic acids (II) can be prepared, for example, according to Scheme 2: Scheme 2
  • azin-2-one-6-carboxylic acid esters (IV) may be e.g. are prepared according to Scheme 3 from the NH-azine-2-one-6-carboxylic acid esters (V):
  • reaction procedure for example, the reaction procedure, the work-up or the Automate cleaning of products or intermediates.
  • this is understood to mean a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (publisher Günther Jung), Verlag Wiley 1999, on pages 1 to 34.
  • 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 invention have an excellent herbicidal
  • Harmful plants that drive off rhizomes, rhizomes or other permanent organs are well detected by the active ingredients.
  • the present invention therefore also provides a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, wherein one or more of the present invention
  • 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 named, 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
  • Crops such as agricultural crops or ornamental plantings.
  • Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, as, for example, storage formation can 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 e.g. of cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potato, cassava, tomato, pea and other vegetables.
  • the compounds of the invention as herbicides in
  • Crop crops are used, which compared to the phytotoxic
  • Glufosinate see, for example, EP-A-0242236, EP-A-242246) or glyphosate
  • transgenic crops for example cotton, with the ability
  • Bacillus thuringiensis toxins Bacillus thuringiensis toxins (Bt toxins) to produce, which the
  • transgenic crops with modified fatty acid composition (WO 91/13972). genetically modified crops with new content or secondary substances z.
  • transgenic crops characterized by a combination z. B. the o. G.
  • 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, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Gene and Clones", VCH Weinheim 2nd edition, 1996
  • the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one
  • Cosuppressions need.es or the expression of at least one appropriately engineered ribozyme that specifically cleaves transcripts of the above gene product.
  • DNA molecules can be used, which cover the entire coding sequence of a gene product including any flanking sequences present, as well as DNA molecules comprising only parts of the coding sequence, which parts must be long enough to cause an antisense effect in the cells. 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,
  • EC emulsifiable concentrates
  • EW emulsions
  • 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),
  • Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agents, dispersants) in addition to the active ingredient except a diluent or inert substance.
  • polyoxyethylated alkylphenols polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate,
  • 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 such as butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more ionic surfactants and / or nonionic type (emulsifiers).
  • emulsifiers which may be used are: alkylarylsulfonic acid calcium salts, such as
  • Ca-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, e.g. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g.
  • 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 be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying
  • Active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites 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 e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils
  • carriers such as sand, kaolinites 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.
  • 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.
  • 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.
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • 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 .-% of 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,
  • Evaporation inhibitors and pH and viscosity affecting agents 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.
  • 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.
  • 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.
  • Q 1 , and R 3 and Y are each methyl.
  • Table 3 Compounds of the invention of the general formula (I) wherein Q is Q 5 , R c1 is hydroxy, R c2 , R c3 , R c4 , R c5 , R c6 and R c7 are each hydrogen, and Y is methyl.
  • 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 inert material and comminuting in a hammer mill.
  • 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
  • a dispersion concentrate readily dispersible in water is obtained by reacting 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
  • 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,
  • a water-dispersible granules are also obtained by
  • the pots After the treatment, the pots are placed in the greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect of the preparations is visually compared to untreated controls in
  • the compounds Nos. 1-27, 1-31, 1-33, 2-3, 2-4 and 2-5 showed a very good herbicidal action at a cost of 0.32 kg of active ingredient or less per hectare (80% to 100% herbicidal activity) against harmful plants such as Pharbitis purpureum, and for example, the compounds Nos. 1-5, 1 -27, 1 -33 and 2-6 against harmful plants such as Echinochloa crus-galli and Stellaria media.
  • compounds according to the invention leave gramineous crops such as barley, wheat, rye, millet, maize or rice in postemergence even at high levels

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Abstract

Disclosed are 6-azinone-2-carbonyl derivatives of general formula (I) as herbicides. In said formula (I), Y and Z represent groups such as hydrogen, organic groups such as alkyl, and other groups such as halogen. X1 and X2 represent nitrogen or carbon and Q represents an azolylcarbamoyl group.

Description

6-Azinon-2-carbonyl-derivate und ihre Verwendung als Herbizide  6-Azino-2-carbonyl derivatives and their use as herbicides
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.
Aus WO2012/039141 A1 sind 6-Pyridon-2-carbonylcyclohexandione und 6-Pyridon-2- carbonylpyrazole als Herbizide beschrieben. Aus der prioritätsälteren, nicht WO2012 / 039141 A1 describes 6-pyridone-2-carbonylcyclohexanediones and 6-pyridone-2-carbonyl-pyrazoles as herbicides. From the priority senior, not
vorveröffentlichten europäischen Patentanmeldung Nr. 12166629 sind 6-Pyridon-2- carbamoyl-azole als Herbizide bekannt. Allerdings zeigen diese Wirkstoffe nicht immer eine ausreichende Wirkung gegen Schadpflanzen und/oder sie sind zum Teil nicht ausreichend verträglich mit einigen wichtigen Kulturpflanzen, wie Getreidearten, Mais und Reis. Aufgabe der vorliegenden Erfindung ist es, alternative herbizid wirksame Wirkstoffe bereitzustellen. Diese Aufgabe wird durch die nachfolgend beschriebenen European patent application No. 12166629, 6-pyridone-2-carbamoyl-azoles are known as herbicides. However, these drugs do not always have a sufficient effect against harmful plants and / or they are sometimes not sufficiently compatible with some important crops, such as cereals, corn and rice. Object of the present invention is to provide alternative herbicidal active ingredients. This task is described by the following
erfindungsgemäßen 6-Azinon-2-carbonyl-derivate gelöst. 6-azino-2-carbonyl derivatives of the invention are dissolved.
Ein Gegenstand der vorliegenden Erfindung sind somit 6-Azinon-2-carbonyl-derivate der Formel (I) oder deren Salze An object of the present invention are thus 6-azino-2-carbonyl derivatives of the formula (I) or salts thereof
Figure imgf000002_0001
worin
Figure imgf000002_0001
wherein
Q bedeutet einen Rest Q1, Q2, Q3, Q4, Q5, Q6, Q7 oder Q8, Q is a radical Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , Q 7 or Q 8 ,
Figure imgf000003_0001
Figure imgf000003_0001
Figure imgf000003_0002
Figure imgf000003_0002
Q5 Q6 Q7 Q8 Q 5 Q 6 Q 7 Q 8
R3 bedeutet (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, wobei diese Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Hydroxy, Nitro, SiR10 3, PO(OR10)2, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, COR3a, COOR3a, OCOR3a, NR3aCOR3a, NR3aSO2R3b, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocyclyl oder Phenyl substituiert sind, wobei die 4 letztgenannten Reste jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluornnethyl, Cyano und Halogen substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, oder R 3 is (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, where these radicals are each represented by s radicals from the group consisting of halogen, cyano, hydroxyl, nitro, SiR 10 3, PO (OR 10) 2, S (O) n - (Ci-C 6) -alkyl, (Ci-C 6) alkoxy, halo (Ci-C 6) alkoxy, COR 3a , COOR 3a , OCOR 3a , NR 3a COR 3a , NR 3a SO 2 R 3b , (C 3 -C 6 ) cycloalkyl, heteroaryl, heterocyclyl or phenyl are substituted, wherein the 4 latter radicals each by p radicals from the group from methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and wherein heterocyclyl n carries oxo groups, or
R3 bedeutet durch p Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C4)-alkyl substituiertes Phenyl, R 3 means by p radicals from the group consisting of halogen, nitro, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, S (O ) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -alkyl-substituted phenyl,
R3a bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl oder (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 3a is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl or (C 3 -C 6 ) - Cycloalkyl- (C 1 -C 6) -alkyl or phenyl,
R3b bedeutet (Ci -C6)-Al kyl , (C2-C6)-Al kenyl oder (C2-C6)-Al kinyl , (C3-C6)-Cycloal kyl oder (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 3b represents (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl or (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl or (C3-C6 ) Cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
R4 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C3-C7)-cyclo-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (C2-C6)-Al kenyl, (C2-C6)-Alkenyloxy, (C2-C6)- Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Alkinyloxy, (C2-C6)-Halogenalkinyl, (Ci-C6)- Alkoxy-(Ci-C6)-Alkyl, Cyano, Nitro, Methylsulfenyl, Methylsulfinyl, Methylsulfonyl, Acetylamino, Benzoylamino, Methoxycarbonyl, Ethoxycarbonyl, R 4 represents hydrogen, (Ci-C 6) -alkyl, (C 3 -C 7) -cycloalkyl, halo (Ci-C 6) alkyl, (Ci-Ce) alkoxy, halo (Ci- C 6) alkoxy, (C 2 -C 6) -alkenyl, (C 2 -C 6) alkenyloxy, (C 2 -C 6) - haloalkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) alkynyloxy, (C 2 -C 6) haloalkynyl, (Ci-C6) - alkoxy- (Ci-C6) alkyl, cyano-, nitro-, methylsulphenyl, methylsulphinyl, methylsulphonyl, Acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl,
Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Benzoyl, Methylcarbonyl, Methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl,
Piperidinylcarbonyl, Trifluormethylcarbonyl, Halogen, Amino, Aminocarbonyl, Piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl,
Methylaminocarbonyl, Dimethylanninocarbonyl, Methoxymethyl, Methylaminocarbonyl, dimethylanninocarbonyl, methoxymethyl,
oder jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl und Halogen substituiertes Heteroaryl, Heterocyclyl oder Phenyl, or in each case by p radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen-substituted heteroaryl, heterocyclyl or phenyl,
R5 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-Alkyl, CH2R5a, (C3- C7)-Cycloalkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2- Ce)-Alkinyl, Halogen-(C2-C6)-alkinyl, OR6, NHR6, Methoxycarbonyl, Ethoxycarbonyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Methylcarbonyl, R 5 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, CH 2 R 5a, (C 3 - C 7) cycloalkyl, halo ( Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C2-C6) alkenyl, (C2 - Ce) alkynyl, halo (C2-C6) alkynyl, OR 6, NHR 6 , methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methylcarbonyl,
Trifluormethylcarbonyl, Dimethylamino, Acetylamino, Methylsulfenyl, Methylsulfinyl, Methylsulfonyl oder jeweils durch p Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C )-alkyl Trifluoromethylcarbonyl, dimethylamino, acetylamino, methylsulfenyl, methylsulfinyl, methylsulfonyl or in each case by p radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 4 ) -alkyl C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- Ci-C) -alkyl
substituiertes Heteroaryl, Heterocyclyl, Benzyl oder Phenyl, substituted heteroaryl, heterocyclyl, benzyl or phenyl,
R5a bedeutet Acetoxy, Acetamido, N-Methylacetamido, Benzoyloxy, Benzamido, N- Methylbenzamido, Methoxycarbonyl, Ethoxycarbonyl, Benzoyl, Methylcarbonyl, Piperidinylcarbonyl, Morpholinylcarbonyl, Trifluormethylcarbonyl, Aminocarbonyl,R 5a represents acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl,
Methylaminocarbonyl, Dimethylaminocarbonyl, (Ci-C6)-Alkoxy, (C3-C6)-Cycloalkyl oder jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Methylaminocarbonyl, dimethylaminocarbonyl, (C 1 -C 6) -alkoxy, (C 3 -C 6) -cycloalkyl or in each case by p radicals from the group consisting of methyl, ethyl, methoxy,
Trifluormethyl und Halogen substituiertes Heteroaryl oder Heterocyclyl, W bedeutet O, CO oder CRc6Rc7, Trifluoromethyl and halogen substituted heteroaryl or heterocyclyl, W is O, CO or CR c6 R c7 ,
Rc1 bedeutet Hydroxy oder SR11 , R c1 is hydroxy or SR 11 ,
Rc2 und Rc5 bedeuten unabhängig voneinander jeweils Wasserstoff oder (Ci-C4)- Alkyl, oder R c2 and R c5 are each independently hydrogen or (Ci-C 4 ) - alkyl, or
Rc2 und Rc5 bilden gemeinsam eine Ethylen- oder Vinylengruppe, R c2 and R c5 together form an ethylene or vinylene group,
Rc3, Rc4, Rc6 und Rc7 bedeuten unabhängig voneinander jeweils Wasserstoff oder (Ci- C4)-Alkyl, RP1 bedeutet Wasserstoff, (Ci-C6)-Alkylsulfonyl, (Ci-C )-Alkoxy-(Ci-C6)- alkylsulfonyl, oder jeweils durch m gleiche oder verschiedene Reste aus der Gruppe bestehend aus Halogen, (Ci-C4)-Alkyl und (Ci-C4)-Alkoxy substituiertes R c3 , R c4 , R c6 and R c7 are each independently hydrogen or (C 1 -C 4 ) -alkyl, RP 1 is hydrogen, (Ci-C 6 ) alkylsulfonyl, (Ci-C) alkoxy- (Ci-C 6 ) - alkylsulfonyl, or in each case by m identical or different radicals from the group consisting of halogen, (Ci-C 4 ) -alkyl and (C 1 -C 4 ) -alkoxy substituted
Phenylsulfonyl, Thiophenyl-2-sulfonyl, Benzoyl, Benzoyl-(Ci-C6)-alkyl oder Benzyl, Phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl- (C 1 -C 6) -alkyl or benzyl,
Rp2 bedeutet (Ci-C4)-Alkyl, R p2 is (C 1 -C 4 ) -alkyl,
RP3 bedeutet Wasserstoff, (Ci-C )-Alkyl, (C3-C8)-Cycloalkyl, (Ci-C )-Alkyl-(C3-C8)- cycloalkyl, (C3-C6)-Halogencycloalkyl, RP 3 is hydrogen, (C 1 -C 4) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 1 -C 4) -alkyl (C 3 -C 8 ) -cycloalkyl, (C 3 -C 6 ) -halocycloalkyl,
Rn1 bedeutet (Ci-C )-Alkyl, (C3-C8)-Cycloalkyl, (Ci-C )-Alkyl-(C3-C8)-cycloalkyl, (C3- C6)-Halogencycloalkyl, Rn2 bedeutet Wasserstoff, CO2(Ci-C6)-Alkyl oder S(O)n(Ci-C6)-Alkyl, R n1 represents (C 1 -C 4) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 1 -C 4) -alkyl (C 3 -C 8 ) -cycloalkyl, (C 3 -C 6 ) -halocycloalkyl, R n2 is hydrogen, CO 2 (C 1 -C 6 ) -alkyl or S (O) n (C 1 -C 6 ) -alkyl,
X1 bedeutet N oder CR2, X 1 is N or CR 2 ,
X2 bedeutet N oder CH, X 2 is N or CH,
mit der Maßgabe, dass mindestens einer der beiden Reste X1 und X2 N bedeutet, with the proviso that at least one of the two radicals X 1 and X 2 is N,
R2 bedeutet Wasserstoff, Halogen, Cyano, Nitro, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (C2-C6)-Alkenyl, (C2-C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3- C6)-Cycloalkyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, (Ci-C )-Alkoxy oder (Ci-C )-Haloalkoxy, R 2 is hydrogen, halogen, cyano, nitro, (Ci-C) alkyl, (Ci-C) -haloalkyl, (C2-C6) alkenyl, (C2-C6) haloalkenyl, (C2-C6 ) alkynyl, (C2-C6) -haloalkynyl, (C3 - C6) cycloalkyl, (C 3 -C 6) halocycloalkyl, (Ci-C6) alkyl-O- (Ci-C 6) - alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, (Ci-C) alkoxy or (Ci-C) haloalkoxy,
Y 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, Halogen-(C3-C6)- cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, OCOOR6, OC(O)N(R6)2, OR6, OCOR6, OSO2R7, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl- OR6, (Ci-C6)-Alkyl-OCOR6, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl- SO2OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-CN, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)- Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR6SO2R7, CH2P(O)(OR10)2, (Ci-C6)-Alkyl-Aryl, (Ci-C6)- Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, wobei die drei letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, (C1-C-6)- Alkyl, Halogen-(Ci-C6)-alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-Ce)- alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Z bedeutet Wasserstoff, Halogen, Cyano, Rhodano, Nitro, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2- C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (Ci-C6)-alkyl-(C3-C6)- cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR6, COOR6, OR6, OCOOR6, NR6COOR6, C(O)N(R6)2, NR6C(O)N(R6)2, Y represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C 2 -C 6) - alkenyl, (C2-C6) - alkynyl, halo (C 3 -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, OCOOR 6 , OC (O) N (R 6 ) 2 , OR 6 , OCOR 6 , OSO 2 R 7 , ( C 1 -C 6 ) -alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl-OR 6 , (C 1 -C 6 ) -alkyl-OCOR 6 , (C 1 -C 6 ) -alkyl-OSO 2 R 7, (Ci-C 6) alkyl-CO 2 R 6, (Ci-C 6) alkyl SO2OR 6, (Ci-C 6) alkyl-CON (R 6) 2, (Ci-C 6) -alkyl-CN, (Ci-C 6) alkyl-SO 2 N (R 6) 2, (Ci-C 6) - alkyl-NR 6 COR 6, (Ci-C 6) alkyl-NR 6 SO 2 R 7 , CH 2 P (O) (OR 10 ) 2 , (C 1 -C 6 ) -alkyl-aryl, (C 1 -C 6 ) -alkyl-heteroaryl, (C 1 -C 6 ) -alkyl-heterocyclyl, where the last three radicals in each case by s radicals from the group consisting of halogen, cyano, nitro, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, S (O) n - (C 1 -C 6 ) -alkyl , (C 1 -C 6) -alkoxy, halogeno (C 1 -C 6) -alkoxy, and where heterocyclyl carries n oxo groups, Z denotes hydrogen, halogen, cyano, rhodano, nitro, (C 1 -C 6) -alkyl, halogeno, (Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C2-C6) alkenyl, (C2-C6) alkynyl, halo (C 2 - C 6) alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (Ci-C6) -alkyl- (C3-C6) - cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6 ) -alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 6 , COOR 6 , OR 6 , OCOOR 6 , NR 6 COOR 6 , C (O) N (R 6 ) 2 , NR 6 C (O) N (R 6 ) 2 ,
OC(O)N(R6)2, C(O)NR6OR6, OSO2R7, S(O)nR7, SO2OR6, SO2N(R6)2, NR6SO2R7, NR6COR6, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)- Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR1SO2R7, N(R6)2, P(O)(OR10)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die drei letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)- Alkoxy oder Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n OC (O) N (R 6 ) 2 , C (O) NR 6 OR 6 , OSO 2 R 7 , S (O) n R 7 , SO 2 OR 6 , SO 2 N (R 6 ) 2 , NR 6 SO 2 R 7 , NR 6 COR 6 , (C 1 -C 6 ) -alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl-OR 6 , (C 1 -C 6 ) -alkyl-OCOR 1 , (Ci-C 6) - alkyl-OSO 2 R 7, (Ci-C 6) alkyl-CO 2 R 6, (Ci-C 6) -alkyl-SO 2 OR 6, (Ci-C 6) alkyl -CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 7 , N (R 6 ) 2 , P (O) (OR 10 ) 2 , heteroaryl, heterocyclyl or phenyl, where the last three radicals are each represented by s radicals selected from the group consisting of halogen, nitro, cyano, ( Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, S (O) n - (Ci-C 6) -alkyl, (Ci-C 6) - Alkoxy or halogeno (Ci-C6) -alkoxy are substituted, and whereby Heterocyclyl n
Oxogruppen trägt, oder Z und R2 bilden gemeinsam mit den beiden Kohlenstoffatomen, an denen sie gebunden sind, einen fünf- oder sechsgliedrigen Ring bestehend aus t Oxo groups, or Z and R 2 form together with the two carbon atoms to which they are attached, a five- or six-membered ring consisting of t
Kohlenstoffatomen und p Heteroatomen aus der Gruppe bestehend aus N, O und S, wobei dieser Ring durch q Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C6)-alkyl substituiert ist, Carbon atoms and p heteroatoms from the group consisting of N, O and S, where this ring is represented by q radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogen- (C 1 -C 6 ) - alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) Alkoxy- (C 1 -C 6 ) -alkyl is substituted,
R6 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C2- C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkenyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-Ce)-Alkyl- Heteroaryl, Heterocycl, (Ci-C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)- Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR8-Heteroaryl, (Ci-C6)-Alkyl-NR8-Heterocyclyl wobei die 21 letztgenannten Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C4)-Alkoxy-(C2-C6)- alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R7 bedeutet (Ci -C6)-Al kyl , (C2-C6)-Al kenyl , (C2-C6)-Al kinyl , (C3-C6)-Cycloal kyl , (C3- C6)-Cycloalkenyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (Ci- C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)-Alkyl-O-Heterocyclyl, (Ci- C6)-Alkyl-NR3-Heteroaryl, (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei diese 17 Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C )-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R8 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 6 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 - C 6) haloalkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 - C 6) cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O - (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-Ce) - alkyl heteroaryl, Heterocycl, (Ci-C 6) alkyl-heterocyclyl, (Ci-C 6) alkyl-O-heteroaryl, (Ci-C 6) - alkyl-O-heterocyclyl, (Ci-C 6) - Alkyl-NR 8 -Heteroaryl, (Ci-C 6 ) -alkyl-NR 8 -Heterocyclyl wherein the 21 latter radicals by s radicals from the group consisting of Cyano, halogen, nitro, Rhodano, OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (Ci-C 4 ) alkoxy- (C 2 -C 6 ) alkoxycarbonyl substituted, and wherein heterocyclyl n carries oxo groups, R 7 is (Ci -C 6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl, (C 3 - C 6) cycloalkenyl, ( C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, ( C 1 -C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl-O-heterocyclyl, (Ci C 6) -alkyl-NR 3 -heteroaryl, (C 1 -C 6) -alkyl-NR 3 -heterocyclyl, where these 17 radicals are represented by s radicals from the group consisting of cyano, halogen, nitro, rhodano, OR 8 , S (O ) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (C 1 -C 4 ) alkoxy- (C 2 -C 6 ) alkoxycarbonyl t, and wherein heterocyclyl carries n oxo groups, R 8 is hydrogen, (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,
R9 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Al kinyl oder Phenyl, R10 bedeutet (Ci-C4)-Al kyl, R 9 is (Ci-C 6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl or phenyl, R 10 is (Ci-C 4) -alkyl,
R11 bedeutet (Ci-C4)-Alkyl oder durch p Reste aus der Gruppe Halogen, Nitro, Cyano, (Ci-C )-Alkyl, (Ci-C )-Halogenalkyl, (Ci-C )-Alkoxy und (Ci-C )-Halogenalkoxy substituiertes Phenyl, n bedeutet 0, 1 oder 2, p bedeutet 0, 1 , 2 oder 3, q bedeutet 0, 1 , 2, 3 oder 4, s bedeutet 0, 1 , 2, 3, 4 oder 5, t bedeutet e 1 , 2, 3, 4, 5 oder 6. 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, R 11 is (C 1 -C 4 ) -alkyl or by p radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkoxy and (C 1 -C 4) -alkyl C) haloalkoxy-substituted phenyl, n is 0, 1 or 2, p is 0, 1, 2 or 3, q is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is e 1, 2, 3, 4, 5 or 6. In formula (I) and all subsequent formulas, alkyl radicals having more than two carbon atoms may be straight-chain or branched. Alkyl radicals are, for example, 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 is for example 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-methyl-but-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 annelliert sein kann. Beispielsweise steht Heterocyclyl für Piperidinyl, Pyrrolidinyl, Tetra hydrofuranyl, Dihydrofuranyl und Oxetanyl, 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 fused by a benzo ring. For example, heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and 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. 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. Die Verbindungen der allgemeinen Formel (I) können je nach Art und Verknüpfung der Substituenten als Stereoisomere vorliegen. Sind beispielsweise ein oder mehrere asymmetrische Kohlenstoffatome vorhanden, so können Enantiomere und 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. 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. 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 asymmetric carbon atoms are present, then enantiomers and
Diastereomere auftreten. Ebenso treten Stereoisomere auf, wenn n für 1 steht Diastereomers occur. Likewise, stereoisomers occur when n is 1
(Sulfoxide). 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 (Sulfoxides). Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods. Likewise, stereoisomers can be prepared by using stereoselective reactions using optically active starting materials and / or
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. Auxiliaries are selectively produced. The invention also relates to all stereoisomers and mixtures thereof which are of the general formula (I), but not specifically defined.
Die Verbindungen der Formel (I) können Salze bilden. Salzbildung kann durch 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 Alkalimetall- salze 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.
Bevorzugt sind Verbindungen der allgemeinen Formel (I), worin Q bedeutet einen Rest Q1, Q2, Q3, Q4, Q5, Q6, Q7 oder Q8, Preference is given to compounds of the general formula (I) in which Q is a radical Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , Q 7 or Q 8 ,
Figure imgf000010_0001
Figure imgf000010_0001
Q5 Q6 Q7 Q8 R3 bedeutet (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, wobei diese Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, S(O)n- (Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocydyl oder Phenyl substituiert sind, wobei die 4 letztgenannten Reste jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl, Cyano und Halogen substituiert sind, und wobei Heterocydyl n Oxogruppen trägt, oder R3 bedeutet durch p Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C4)-alkyl substituiertes Phenyl, R4 bedeutet (Ci-C6)-Alkyl, (C3-C7)-cyclo-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy, Cyano, Nitro, Methylsulfenyl, Methylsulfinyl, Q 5 Q 6 Q 7 Q 8 R 3 represents (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, where these radicals in each case by s radicals selected from the group consisting of halogen, cyano, nitro, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 3 -C 6 ) -cycloalkyl , Heteroaryl, heterocyclic or phenyl, wherein the 4 last-mentioned radicals are each substituted by p radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and wherein heterocyclyl n carries oxo groups, or R 3 is replaced by p radicals from the group consisting of halogen, nitro, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, S (O) n - (C -C 6 ) -alkyl, (Ci-C 6 ) - alkoxy, halogen- (Ci-C6) -alkoxy and (Ci-C6) -alkoxy- (Ci-C 4 ) -alkyl-substituted phenyl, R 4 is (Ci -C 6) alkyl, (C 3 -C 7) -cycloalkyl, halo (Ci-C 6) alkyl, (Ci-C 6) - alkoxy, halo (Ci-C6) alkoxy, cyano , Nitro, methylsulfenyl, methylsulfinyl,
Methylsulfonyl, (Ci-C4)-Alkylcarbonylamino, Benzoylamino, Methoxycarbonyl, Methylsulfonyl, (C 1 -C 4 ) -alkylcarbonylamino, benzoylamino, methoxycarbonyl,
Ethoxycarbonyl, Benzoyl, Phenoxy, Methylcarbonyl, Piperidinylcarbonyl, Ethoxycarbonyl, benzoyl, phenoxy, methylcarbonyl, piperidinylcarbonyl,
Trifluormethylcarbonyl, Halogen, Amino, Aminocarbonyl, Methylaminocarbonyl, Dimethylanninocarbonyl, Methoxymethyl, 1 ,2,4-Triazol-1 -yl, Pyrazol-1 -yl, 2-Thiophenyl, 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 1 ,2,4-Oxadiazol-3-yl, Benzoxazol-2-yl, 1 - Ethylbenzimidazol-2-yl, Piperidin-1 -yl oder jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl und Halogen substituiertes Phenyl, R5 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C3-C7)-Cycloalkyl, Halogen-(Ci-C6)-alkyl, (C3-C7)-Cycloalkylmethyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylanninocarbonyl, methoxymethyl, 1, 2,4-triazol-1-yl, pyrazol-1-yl, 2-thiophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1, 2,4-oxadiazol-3-yl, benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl or phenyl substituted by p radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen . R 5 represents hydrogen, (Ci-C 6) -alkyl, (C 3 -C 7) cycloalkyl, halo (Ci-C 6) alkyl, (C3-C7) cycloalkylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,
Acetylmethyl, Methoxymethyl, Methoxyethyl, Benzyl, Pyrazin-2-yl, Furan-2-yl, Acetylmethyl, methoxymethyl, methoxyethyl, benzyl, pyrazine-2-yl, furan-2-yl,
Tetrahydrofuran-2-yl, Morpholin, Dimethylannino oder durch p Reste aus der Gruppe bestehend aus Methyl, Methoxy, Trifluormethyl und Halogen substituiertes Phenyl, Tetrahydrofuran-2-yl, morpholine, dimethylannino or phenyl substituted by p radicals from the group consisting of methyl, methoxy, trifluoromethyl and halogen,
W bedeutet O, CO oder CRc6Rc7, W is O, CO or CR c6 R c7 ,
Rc1 bedeutet Hydroxy, R c1 is hydroxy,
Rc2 und Rc5 bedeuten unabhängig voneinander jeweils Wasserstoff oder Methyl, oder Rc2 und Rc5 bilden gemeinsam eine Ethylen- oder Vinylengruppe, R c2 and R c5 are each independently hydrogen or methyl, or R c2 and R c5 together form an ethylene or vinylene group,
Rc3, Rc4, Rc6 und Rc7 bedeuten unabhängig voneinander jeweils Wasserstoff oder Methyl, R c3 , R c4 , R c6 and R c7 are each independently hydrogen or methyl,
Rp1 bedeutet Wasserstoff, R p1 is hydrogen,
RP2 bedeutet (Ci-C4)-Alkyl, RP 2 is (C 1 -C 4 ) -alkyl,
Rp3 bedeutet Wasserstoff, (Ci-C )-Alkyl oder Cycloproyl, R p3 is hydrogen, (C 1 -C 4) -alkyl or cyclopropyl,
Rn1 bedeutet Cycloproyl, Rn2 bedeutet Wasserstoff, R n1 is cycloproyl, R n2 is hydrogen,
X1 bedeutet N oder CR2, X 1 is N or CR 2 ,
X2 bedeutet N oder CH, X 2 is N or CH,
mit der Maßgabe, dass mindestens einer der beiden Reste X1 und X2 N bedeutet, with the proviso that at least one of the two radicals X 1 and X 2 is N,
R2 bedeutet Wasserstoff, Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (C2-C6)- Alkenyl, (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, (Ci-C )-Alkoxy oder (Ci-C )-Haloalkoxy, Y 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, Halogen-(C3-C6)- cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, OCOOR6, OC(O)N(R6)2, OR6, OCOR6, OSO2R7, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl- OR6, (Ci-C6)-Alkyl-OCOR6, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl- SO2OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR6SO2R7, CH2P(O)(OR10)2, (Ci-C6)-Alkyl-Aryl, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, wobei die drei letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, (Ci-C6)-Alkyl, Halogen-(Ci-Ce)- alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R 2 is hydrogen, halogen, (Ci-C) alkyl, (Ci-C) -haloalkyl, (C 2 -C 6) - alkenyl, (C2-C6) -alkynyl, (C3-C6) cycloalkyl , (Ci-C6) alkyl-O- (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, (Ci-C) alkoxy or (Ci- C) haloalkoxy, Y represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C2-C6) alkenyl, halo (C 2 -C 6) - alkenyl, (C2-C6) - alkynyl, halo (C3-C6) -alkynyl, (C3-C6) -cycloalkyl, halo- (C3-C6) - cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl , Halogen- (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, OCOOR 6 , OC (O) N (R 6 ) 2 , OR 6 , OCOR 6 , OSO 2 R 7 , (C 1 -C 6 ) -Alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl-OR 6 , (C 1 -C 6 ) -alkyl-OCOR 6 , (C 1 -C 6 ) -alkyl-OSO 2 R 7 , (C 1 -C 6 ) -alkyl-CO 2 R 6 , (C 1 -C 6 ) -alkyl- SO 2 OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -Alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 6 SO 2 R 7 , CH 2 P (O) (OR 10 ) 2 , (C 1 -C 6 ) -alkyl-aryl, (C 1 -C 6 ) -alkyl-heteroaryl, (C 1 -C 6 ) -alkyl-heterocyclyl, where the three last-mentioned radicals are each represented by s radicals from the group consisting of Halogen, cyano, nitro, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy and halogen- Ci-C 6) -alkoxy, and heterocyclyl wherein n tr oxo groups gt,
Z bedeutet Wasserstoff, Halogen, Cyano, Rhodano, Nitro, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2- C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (Cs-CeJ-CycloalkyKCi-Ce)- alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR6, COOR6, OCOOR6, NR6COOR6, C(O)N(R6)2, NR6C(O)N(R6)2, OC(O)N(R6)2, C(O)NR6OR6, OSO2R7, S(O)nR7, SO2OR6, SO2N(R6)2, NR6SO2R7, NR6COR6, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)- Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (Ci- C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl- NR1SO2R7, N(R6)2, P(O)(OR10)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die letzten drei Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-Ce)-Alkoxy oder Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Z is hydrogen, halogen, cyano, thiocyanato, nitro, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, halo (C 2 - C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (Cs-CeJ- CycloalkyKCi-Ce) -alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 6 , COOR 6 , OCOOR 6 , NR 6 COOR 6 , C (O) N (R 6 ) 2 , NR 6 C (O) N (R 6 ) 2 , OC (O) N (R 6 ) 2 , C (O) NR 6 OR 6 , OSO 2 R 7 , S (O) n R 7 , SO 2 OR 6 , SO 2 N (R 6 ) 2 , NR 6 SO 2 R 7 , NR 6 COR 6 , (C 1 -C 6 ) -alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl OR 6, (Ci-C 6) - alkyl-OCOR 1, (Ci-C 6) -alkyl-OSO 2 R 7, (Ci-C 6) alkyl-CO 2 R 6, (Ci-C 6) - Alkyl-SO 2 OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 7 , N (R 6 ) 2 , P (O) (OR 10 ) 2 , heteroaryl, heterocyclyl or phenyl, where the last three radicals are each by s radicals from the group consisting of halogen, nitro, cyano, (Ci-C 6 ) alkyl, Hal o- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy or halogen- (C 1 -C 6 ) -alkoxy are substituted, and wherein
Heterocyclyl n Oxogruppen trägt, Heterocyclyl carries n oxo groups,
Z und R2 bilden gemeinsam mit den beiden Kohlenstoffatomen, an denen sie gebunden sind, einen fünf- oder sechsgliedrigen Ring bestehend aus t Z and R 2 together with the two carbon atoms to which they are attached form a five- or six-membered ring consisting of t
Kohlenstoffatomen und p Heteroatomen aus der Gruppe bestehend aus N, O und S, wobei dieser Ring durch q Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C )-alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy- methyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert ist, R6 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C2- C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkenyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-Ce)-Alkyl- Heteroaryl, Heterocycl, (Ci-C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)- Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR8-Heteroaryl, (Ci-C6)-Alkyl-NR8-Heterocyclyl wobei die 21 letztgenannten Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C4)-Alkoxy-(C2-C6)- alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Carbon atoms and p heteroatoms from the group consisting of N, O and S, where this ring by q radicals from the group consisting of halogen, nitro, cyano, (Ci-C 6 ) alkyl, halogeno (Ci-C) -alkyl , S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxymethyl, (C 1 -C 6 ) -alkoxy and halogeno (C 1 -C 6 ) -alkoxy, R 6 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C2-C6) alkenyl, (C 2 - C 6) haloalkenyl, (C2-C6) alkynyl , (C2-C6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 - C 6) cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O- (C -C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-Ce) alkyl- heteroaryl , Heterocycl, (Ci-C 6) alkyl-heterocyclyl, (Ci-C 6) alkyl-O-heteroaryl, (Ci-C 6) - alkyl-O-heterocyclyl, (Ci-C 6) alkyl-NR 8- heteroaryl, (C 1 -C 6 ) -alkyl-NR 8 -heterocyclyl where the 21 latter radicals are represented by s radicals from the group consisting of cyano, halogen, nitro, Rhodano, OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (Ci-C 4 ) Alkoxy- (C 2 -C 6 ) alkoxycarbonyl, and wherein heterocyclyl carries n oxo groups,
R7 bedeutet (Ci -C6)-Al kyl , (C2-C6)-Al kenyl , (C2-C6)-Al kinyl , (C3-C6)-Cycloal kyl , (C3- C6)-Cycloalkenyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (Ci- C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)-Alkyl-O-Heterocyclyl, (Ci- C6)-Alkyl-NR3-Heteroaryl, (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei diese 17 Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C )-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R 7 is (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl, (C 3 - C 6 ) -cycloalkenyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl -O-heterocyclyl, (C 1 -C 6) -alkyl-NR 3 -heteroaryl, (C 1 -C 6) -alkyl-NR 3 -heterocyclyl, wherein these 17 radicals are represented by s radicals from the group consisting of cyano, halogen, nitro, rhodano , OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (C 1 -C 4 ) -alkoxy- (C 2 -C 6 ) -alkoxycarbonyl, and wherein heterocyclyl carries n oxo groups,
R8 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R9 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Alkinyl oder Phenyl, R 8 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) cycloalkyl (Ci-C 6) alkyl or phenyl, R 9 is (Ci-C 6) -alkyl, represents (C 2 -C 6) -alkenyl, (C 2 -C 6) alkynyl or phenyl,
R10 bedeutet (Ci-C4)-Alkyl, n bedeutet 0, 1 oder 2, R 10 is (C 1 -C 4 ) -alkyl, n is 0, 1 or 2,
P bedeutet 0, 1 , 2 oder 3, q bedeutet 0, 1 , 2, 3 oder 4, s bedeutet 0, 1 , 2, 3, 4 oder 5, t bedeutet e 1 , 2, 3, 4, 5 oder 6. P is 0, 1, 2 or 3, q is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is e 1, 2, 3, 4, 5 or 6.
Besonders bevorzugt sind Verbindungen der allgemeinen Formel (I), Q bedeutet einen Rest Q1, Q2, Q3, Q4, Q5, Q6, Q7 oder Q8, Particular preference is given to compounds of the general formula (I), Q denotes a radical Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , Q 7 or Q 8 ,
Figure imgf000014_0001
Figure imgf000014_0001
Q5 Q6 Q7 Q8 Q 5 Q 6 Q 7 Q 8
R3 bedeutet jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiertes (Ci-C8)-Alkyl, (C2-C8)-Alkenyl oder (C2-C8)-Alkinyl, R 3 is in each case by s radicals from the group consisting of halogen, cyano, nitro, S (O) n- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy and halogen (C 1 -C 6 ) alkoxy-substituted (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl or (C 2 -C 8 ) -alkynyl,
R4 bedeutet (Ci-C6)-Alkyl, (C3-C7)-cyclo-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy, Cyano, Nitro, Methylsulfenyl, Methylsulfinyl, R 4 is (Ci-C 6) -alkyl, (C 3 -C 7) -cycloalkyl, halo (Ci-C 6) alkyl, (Ci-C 6) - alkoxy, halo (Ci-C6 ) -alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl,
Methylsulfonyl, (Ci-C4)-Alkylcarbonylamino, Benzoylamino, Methoxycarbonyl, Methylsulfonyl, (C 1 -C 4 ) -alkylcarbonylamino, benzoylamino, methoxycarbonyl,
Ethoxycarbonyl, Benzoyl, Phenoxy, Methylcarbonyl, Piperidinylcarbonyl, Ethoxycarbonyl, benzoyl, phenoxy, methylcarbonyl, piperidinylcarbonyl,
Trifluormethylcarbonyl, Halogen, Amino, Aminocarbonyl, Methylaminocarbonyl, Dimethylaminocarbonyl, Methoxymethyl, 1 ,2,4-Triazol-1 H, 1 -Pyrazol-1 H, 2-Thiophenyl, 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 1 ,2,4-Oxadiazol-3-yl, Benzoxazol-2-yl, Trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, 1, 2,4-triazole-1H, 1-pyrazole-1H, 2-thiophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1, 2,4-oxadiazol-3-yl, benzoxazol-2-yl,
1 Ethylbenzimidazol-2-yl, Piperidin-1 -yl oder durch s Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl und Halogen substituiertes Phenyl, R5 bedeutet Wassetrstoff, (Ci-C6)-Alkyl, (C3-C7)-Cycloalkyl, Halogen-(Ci-C6)-alkyl, (C3-C7)-Cycloalkylmethyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, 1 ethylbenzimidazol-2-yl, piperidin-1-yl or phenyl substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen, R 5 represents Wassetrstoff, (Ci-C 6) -alkyl, (C 3 -C 7) cycloalkyl, halo (Ci-C 6) alkyl, (C3-C7) cycloalkylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,
Acetylmethyl, Methoxymethyl, Methoxyethyl, Benzyl, Pyrazin-2-yl, Furan-2-yl, Acetylmethyl, methoxymethyl, methoxyethyl, benzyl, pyrazine-2-yl, furan-2-yl,
Tetrahydrofuran-2-yl, Morpholin, Dimethylannino oder durch p Reste aus der Gruppe bestehend aus Methyl, Methoxy, Trifluormethyl und Halogen substituiertes Phenyl, Tetrahydrofuran-2-yl, morpholine, dimethylannino or phenyl substituted by p radicals from the group consisting of methyl, methoxy, trifluoromethyl and halogen,
W bedeutet O, CO oder CRc6Rc7, W is O, CO or CR c6 R c7 ,
Rc1 bedeutet Hydroxy, R c1 is hydroxy,
Rc2 und Rc5 bedeuten unabhängig voneinander jeweils Wasserstoff oder Methyl, oder Rc2 und Rc5 bilden gemeinsam eine Ethylen- oder Vinylengruppe, R c2 and R c5 are each independently hydrogen or methyl, or R c2 and R c5 together form an ethylene or vinylene group,
Rc3, Rc4, Rc6 und Rc7 bedeuten unabhängig voneinander jeweils Wasserstoff oder Methyl, R c3 , R c4 , R c6 and R c7 are each independently hydrogen or methyl,
Rp1 bedeutet Wasserstoff, R p1 is hydrogen,
RP2 bedeutet (Ci-C4)-Alkyl, RP 2 is (C 1 -C 4 ) -alkyl,
Rp3 bedeutet Wasserstoff, (Ci-C )-Alkyl oder Cycloproyl, R p3 is hydrogen, (C 1 -C 4) -alkyl or cyclopropyl,
Rn1 bedeutet Cycloproyl, Rn2 bedeutet Wasserstoff, R n1 is cycloproyl, R n2 is hydrogen,
X1 bedeutet N oder CR2, X 1 is N or CR 2 ,
X2 bedeutet N oder CH, X 2 is N or CH,
mit der Maßgabe, dass mindestens einer der beiden Reste X1 und X2 N bedeutet, with the proviso that at least one of the two radicals X 1 and X 2 is N,
R2 bedeutet Wasserstoff, Halogen, (Ci-C )-Alkyl, Y bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, OR6, S(O)nR7, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl- SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR6SO2R7, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, wobei die beiden letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R 2 is hydrogen, halogen, (C 1 -C 4) -alkyl, Y represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C3-C6) cycloalkyl, OR 6, S (O) n R 7, (Ci-C 6) alkyl -S (O) n R 7 , (C 1 -C 6 ) -alkyl-OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N ( R 6 ) 2 , (C 1 -C 6 ) -alkyl-NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 6 SO 2 R 7 , (C 1 -C 6 ) -alkyl heteroaryl, (C 1 -C 6 ) -Alkyl-heterocyclyl, where the latter two radicals in each case by s radicals from the group consisting of halogen, (Ci-C6) alkyl, halogeno (Ci-C6) alkyl, S (O) n - (Ci-C6 ) Alkyl, (C 1 -C 6) -alkoxy and halo (C 1 -C 6) -alkoxy, and where heterocyclyl carries n oxo groups,
Z bedeutet Wasserstoff, Halogen, Cyano, Rhodano, Nitro, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2- C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (Cs-CeJ-CycloalkyKCi-Ce)- alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR6, COOR6, OCOOR6, NR6COOR6, C(O)N(R6)2, NR6C(O)N(R6)2, OC(O)N(R6)2, C(O)NR6OR6, OSO2R7, S(O)nR7, SO2OR6, SO2N(R6)2, NR6SO2R7, NR6COR6, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)- Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (Ci- C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl- NR1SO2R7, N(R6)2, P(O)(OR10)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die 3 letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Z is hydrogen, halogen, cyano, thiocyanato, nitro, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, halo (C 2 - C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (Cs-CeJ- CycloalkyKCi-Ce) -alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 6 , COOR 6 , OCOOR 6 , NR 6 COOR 6 , C (O) N (R 6 ) 2 , NR 6 C (O) N (R 6 ) 2 , OC (O) N (R 6 ) 2 , C (O) NR 6 OR 6 , OSO 2 R 7 , S (O) n R 7 , SO 2 OR 6 , SO 2 N (R 6 ) 2 , NR 6 SO 2 R 7 , NR 6 COR 6 , (C 1 -C 6 ) -alkyl-S (O) n R 7 , (C 1 -C 6 ) -alkyl OR 6, (Ci-C 6) - alkyl-OCOR 1, (Ci-C 6) -alkyl-OSO 2 R 7, (Ci-C 6) alkyl-CO 2 R 6, (Ci-C 6) - Alkyl-SO 2 OR 6 , (C 1 -C 6 ) -alkyl-CON (R 6 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 6 ) 2 , (C 1 -C 6 ) -alkyl NR 6 COR 6 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 7 , N (R 6 ) 2 , P (O) (OR 10 ) 2 , heteroaryl, heterocyclyl or phenyl, where the 3 last-mentioned radicals in each case by radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, Halo (Ci-C 6) alkyl, (C3-C6) -cycloalkyl, S (O) n - (Ci-C 6) - alkyl, (Ci-Ce) alkoxy and halo (Ci-C6) -alkoxy are substituted, and wherein
Heterocyclyl n Oxogruppen trägt, Heterocyclyl carries n oxo groups,
Z und R2 bilden gemeinsam mit den beiden Kohlenstoffatomen, an denen sie gebunden sind, einen fünf- oder sechsgliedrigen Ring bestehend aus t Z and R 2 together with the two carbon atoms to which they are attached form a five- or six-membered ring consisting of t
Kohlenstoffatomen und p Heteroatomen aus der Gruppe bestehend aus N, O und S, wobei dieser Ring durch q Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C )-alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy- methyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert ist, R6 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C2- C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkenyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-Ce)-Alkyl- Heteroaryl, Heterocycl, (Ci-C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)- Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR8-Heteroaryl, (Ci-C6)-Alkyl-NR8-Heterocyclyl wobei die 21 letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C4)-Alkoxy-(C2-C6)- alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Carbon atoms and p heteroatoms from the group consisting of N, O and S, where this ring by q radicals from the group consisting of halogen, nitro, cyano, (Ci-C 6 ) alkyl, halogeno (Ci-C) -alkyl , S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxymethyl, (C 1 -C 6 ) -alkoxy and halo (C 1 -C 6 ) -alkoxy, R 6 is hydrogen , (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 - C 6) haloalkenyl, (C 2 -C 6) -alkynyl, ( C 2 -C 6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 - C 6) cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) -alkyl-O- (Ci- C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-Ce) alkyl- heteroaryl, Heterocycl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) - Alkyl-O-heterocyclyl, (C 1 -C 6 ) -alkyl-NR 8 -heteroaryl, (C 1 -C 6 ) -alkyl-NR 8 -heterocyclyl where the last 21 radicals are each represented by s radicals from the group consisting of cyano, halogen , Nitro, Rhodano, OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (C 1 -C 4 ) -alkoxy- (C 2 -C 6 ) -alkoxycarbonyl, and where heterocyclyl carries n oxo groups,
R7 bedeutet (Ci -C6)-Al kyl , (C2-C6)-Al kenyl , (C2-C6)-Al kinyl , (C3-C6)-Cycloal kyl , (C3- C6)-Cycloalkenyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (Ci- C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)-Alkyl-O-Heterocyclyl, (Ci- C6)-Alkyl-NR3-Heteroaryl, (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei diese 17 Reste jeweils durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C )-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R 7 is (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl, (C 3 - C 6 ) -cycloalkenyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl -O-heterocyclyl, (C 1 -C 6) -alkyl-NR 3 -heteroaryl, (C 1 -C 6) -alkyl-NR 3 -heterocyclyl, where these 17 radicals are in each case represented by s radicals from the group consisting of cyano, halogen, nitro, Rhodano, OR 8 , S (O) n R 9 , N (R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (C 1 -C 4 ) -alkoxy- (C 2 -C 6 ) -alkoxycarbonyl, and where heterocyclyl carries n oxo groups,
R8 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R9 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Alkinyl oder Phenyl, R 8 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) cycloalkyl (Ci-C 6) alkyl or phenyl, R 9 is (Ci-C 6) -alkyl, represents (C 2 -C 6) -alkenyl, (C 2 -C 6) alkynyl or phenyl,
R10 bedeutet (Ci-C4)-Alkyl, n bedeutet 0, 1 oder 2, R 10 is (C 1 -C 4 ) -alkyl, n is 0, 1 or 2,
P bedeutet 0, 1 , 2 oder 3, q bedeutet 0, 1 , 2, 3 oder 4, s bedeutet 0, 1 , 2, 3, 4 oder 5, t bedeutet e 1 , 2, 3, 4, 5 oder 6. In allen nachfolgend genannten Formeln haben die Substituenten und Symbole, sofern nicht anders definiert, dieselbe Bedeutung wie unter Formel (I) beschrieben. P is 0, 1, 2 or 3, q is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is e 1, 2, 3, 4, 5 or 6 , In all of the formulas below, the substituents and symbols, unless otherwise defined, have the same meaning as described for formula (I).
Erfindungsgemäße Verbindungen mit Q = Q1, Q2, Q3 oder Q4 können beispielsweise gemäß Schema 1 analog den in WO2012/039141 A1 , WO 2012/123416 A1 und WO2012/126932 A1 genannten Methoden durch Reaktion eines Amins Q1-H, Q2-H, Q3-H oder Q4-H mit einem Säurechlorid der Formel (II) hergestellt werden. According to Scheme 1, compounds according to the invention having Q = Q 1 , Q 2 , Q 3 or Q 4 can be prepared analogously to the methods mentioned in WO2012 / 039141 A1, WO 2012/123416 A1 and WO2012 / 126932 A1 by reaction of an amine Q 1 -H, Q 2 -H, Q 3 -H or Q 4 -H are prepared with an acid chloride of formula (II).
Schema 1 Scheme 1
Figure imgf000018_0001
Figure imgf000018_0001
Q3-H Q4-H Q 3 -HQ 4 -H
Erfindungsgemäße Verbindungen mit Q = Q5, Q6, Q7 oder Q8 können beispielsweise analog den in WO 2009/018925 A1 genannten Methoden hergestellt werden. Compounds according to the invention having Q = Q 5 , Q 6 , Q 7 or Q 8 can be prepared, for example, analogously to the methods mentioned in WO 2009/018925 A1.
Die Azin-2-on-6-carbonsäurechloride (II) beziehungsweise die ihnen zugrunde liegenden Azin-2-on-6-carbonsäuren (II) können z.B. nach Schema 2 hegestellt werden: Schema 2 The azin-2-one-6-carboxylic acid chlorides (II) or their underlying azin-2-one-6-carboxylic acids (II) can be prepared, for example, according to Scheme 2: Scheme 2
Figure imgf000019_0001
Figure imgf000019_0001
(I)  (I)
Die Azin-2-on-6-carbonsäureester (IV) können z.B. nach Schema 3 aus den NH-Azin- 2-on-6-carbonsäureestern (V) hergestellt werden: The azin-2-one-6-carboxylic acid esters (IV) may be e.g. are prepared according to Scheme 3 from the NH-azine-2-one-6-carboxylic acid esters (V):
Schema 3 Scheme 3
Figure imgf000019_0002
Figure imgf000019_0002
(V) (IV)  (V) (IV)
Es kann zweckmäßig sein, Reaktionsschritte in ihrer Reihenfolgezu 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. 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.
Kollektionen aus Verbindungen der Formel (I) und/oder deren Salzen, die nach den oben genannten Reaktionen synthetisiert werden können, können auch in 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 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. automated or completely automated way. It is possible, for example, the reaction procedure, the work-up or the Automate cleaning of products or intermediates. Overall, this is understood to mean a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (publisher Günther Jung), Verlag Wiley 1999, on pages 1 to 34.
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, 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 1 1 3AZ, England oder Dubuque, Iowa 52004-0797, USA or reaction stations from Radleys, Shirehill, Saffron Waiden, Essex, CB 1 1 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 Combinato al 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 Combinato al 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 weisen eine ausgezeichnete herbizide The compounds of the invention have an excellent herbicidal
Wirksamkeit gegen ein breites Spektrum wirtschaftlich wichtiger mono- und dikotyler annueller Schadpflanzen auf. Auch schwer bekämpfbare perennierende Effectiveness against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Also difficult to combat perennial
Schadpflanzen, die aus Rhizomen, Wurzelstöcken oder anderen Dauerorganen austreiben, werden durch die Wirkstoffe gut erfasst.  Harmful plants that drive off rhizomes, rhizomes or other permanent organs are well detected by the active ingredients.
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 present invention therefore also provides a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, wherein one or more of the present invention
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 die erfindungsgemäßen Verbindungen kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll. 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 named, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species.
Monokotyle Schadpflanzen der Gattungen: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria und Sorghum. Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata , Ishamedum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, and 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 und 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 and 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. Obgleich die erfindungsgemäßen Verbindungen eine ausgezeichnete herbizide When the active ingredients are applied to the green parts of the plants postemergence, growth stops after the treatment and the harmful plants remain in the growth stage existing at the time of application or die completely after a certain time, so that a weed competition harmful to the crop plants takes place very early and sustainably eliminated. 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, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, oder monokotyler Kulturen der Gattungen Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, insbesondere Zea und Triticum, abhängig von der Struktur der jeweiligen erfindungsgemäßen Verbindung und deren Aufwandmenge nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the genera Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea , in particular Zea and Triticum, depending on the structure of the respective compound of the invention and their application rate only insignificantly or not at all damaged. 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.
Darüber hinaus weisen die erfindungsgemäßen Verbindungen, abhängig von ihrer jeweiligen chemischen Struktur und der ausgebrachten Aufwandmenge, In addition, the compounds of the invention, depending on their respective chemical structure and the applied application rate,
hervorragende wachstumsregulatorische Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Beeinflussung von Pflanzeninhaltsstoffen und zur Ernteerleichterung wie z.B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Des excellent growth regulatory properties in crops. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, such as be used by triggering desiccation and stunted growth. Of
Weiteren eignen sie sich auch zur generellen Steuerung und Hemmung von Furthermore, they are also suitable for the general control and inhibition of
unerwünschtem vegetativen Wachstum, ohne dabei die Pflanzen abzutöten. Eineundesirable vegetative growth without killing the plants. A
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. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, as, for example, storage formation can 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 relate eg to 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, Maniok, Tomate, Erbse und anderen Gemüsesorten. Ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potato, cassava, tomato, pea and other vegetables.
Vorzugsweise können die erfindungsgemäßen Verbindungen als Herbizide in Preferably, the compounds of the invention as herbicides in
Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischenCrop crops are used, which compared to the phytotoxic
Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. Effects of the herbicides are resistant 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,  genetic modification of crops for the purpose of modifying the starch synthesized in the plants (eg WO 92/1 1376, WO 92/14827,
WO 91/19806),  WO 91/19806),
transgene Kulturpflanzen, welche gegen bestimmte Herbizide vom Typ  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-5013659) resistent sind,  (WO 92/00377) or the sulfonylureas (EP-A-0257993, US-A-5013659) are resistant,
transgene Kulturpflanzen, beispielsweise Baumwolle, mit der Fähigkeit  transgenic crops, for example cotton, with the ability
Bacillus thuringiensis-Toxine (Bt-Toxine) zu produzieren, welche die  Bacillus thuringiensis toxins (Bt toxins) to produce, which the
Pflanzen gegen bestimmte Schädlinge resistent machen (EP-A-0142924, EP-A-0193259).  Make plants resistant to certain pests (EP-A-0142924, EP-A-0193259).
- transgene Kulturpflanzen mit modifizierter Fettsäurezusammensetzung (WO 91/13972). gentechnisch veränderte Kulturpflanzen mit neuen Inhalts- oder Sekundärstoffen z. B. neuen Phytoalexinen, die eine erhöhte transgenic crops with modified fatty acid composition (WO 91/13972). genetically modified crops with new content or secondary substances 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.  transgenic crops characterized by a combination z. B. the o. G.
neuen Eigenschaften auszeichnen („gene stacking")  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 et al., 1989, Molecular Cloning, A Laboratory Manual, 2. Aufl. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, oder Winnacker "Gene und Klone", VCH Weinheim 2. Auflage 1996 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, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Gene and Clones", VCH Weinheim 2nd edition, 1996
Die Herstellung von Pflanzenzellen mit einer verringerten Aktivität eines Genprodukts kann beispielsweise erzielt werden durch die Expression mindestens einer The production of plant cells having 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
Cosuppressionseffekt.es 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. Cosuppressionseffekt.es or the expression of at least one appropriately engineered ribozyme that specifically cleaves transcripts of the above gene product. For this purpose, on the one hand DNA molecules can be used, which cover the entire coding sequence of a gene product including any flanking sequences present, as well as DNA molecules comprising only parts of the coding sequence, which parts must be long enough to cause an antisense effect in the cells. 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.
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. Bei der Anwendung der erfindungsgemäßen Wirkstoffe in transgenen Kulturen treten neben den in anderen Kulturen zu beobachtenden Wirkungen gegenüber 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. 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. Crops.
Die erfindungsgemäßen Verbindungen können in Form von Spritzpulvern, 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, 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,
emulgierbare Konzentrate (EC), Emulsionen (EW), wie Öl-in-Wasser- und emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and
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), 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. Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise Volume 7, C. Hanser Verlag Munich, 4th ed. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973, K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd. London. 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. Äthylenoxidaddukte ", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler," Chemical Technology ", Volume 7, C. Hanser Verlag Munich, 4th ed. 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 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. Suitable safeners are
beispielsweise Mefenpyr-diethyl, Cyprosulfamid, Isoxadifen-ethyl, Cloquintocet-mexyl und Dichlormid. 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, for example, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and dichloromide. Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agents, dispersants) in addition to the active ingredient except a diluent or inert substance. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate,
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. 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleoylmethyltaurine acid. 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, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen oder Mischungen der organischen Lösungsmittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calzium-Salze wie organic solvents such as butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more ionic surfactants and / or nonionic type (emulsifiers). Examples of emulsifiers which may be used are: alkylarylsulfonic acid calcium salts, such as
Ca-Dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as
Fettsäurepolyglykolester, Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers,
Propylenoxid-Ethylenoxid-Kondensationsprodukte, Alkylpolyether, Sorbitanester wie z.B. Sorbitanfettsäureester oder Polyoxethylensorbitanester wie z.B. Propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, e.g. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g.
Polyoxyethylensorbitanfettsäureester. Polyoxyethylene.
Stäubemittel erhält man durch Vermählen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, oder Diatomeenerde. 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 Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying
Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden. Active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites 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. Zur Herstellung von Teller-, Fließbett-, Extruder- und Sprühgranulate siehe z.B. 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. For the preparation of plate, fluidized bed, extruder and spray granules see, for example
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 emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 1 bis 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 In wettable powders, the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients. For emulsifiable concentrates, the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%. 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 .-% of 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. 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. Evaporation inhibitors and pH and viscosity affecting agents. 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 are present in commercial form formulations optionally diluted in a customary manner, for example with 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
1 . Synthese von 1 -Methyl-3-phenyl-N-(1 -methyltetrazol-5-yl)-pyrazin-2-on-6- carbonsäureamid, (Tabellenbeispiel Nr. 1 -7 ) 1 . Synthesis of 1-methyl-3-phenyl-N- (1-methyltetrazol-5-yl) -pyrazine-2-one-6-carboxylic acid amide, (Table Example No. 1-7)
Eine mischun von 4.5 g ( 30 mmol) Phenylglyoxylsäure, 4.2 g (30 mmol)  A mixture of 4.5 g (30 mmol) phenylglyoxylic acid, 4.2 g (30 mmol)
Sarcosinmethylesterhydrochlorid und 3.9 g (30 mmol) Diisopropylethylamin in 60 ml Dichlormethan wird bei 0°C mit 5.7 g (30 mmol) EDAC versetzt. Nach 5 h Rühren bei Raumtemp. wird die Mischung mit Wasser, 2N Salzsäure, ges. Sarcosine methyl ester hydrochloride and 3.9 g (30 mmol) of diisopropylethylamine in 60 ml of dichloromethane are treated at 0 ° C with 5.7 g (30 mmol) of EDAC. After stirring for 5 h at room temp. the mixture is washed with water, 2N hydrochloric acid, sat.
Natriumhydrogencarbonatlösung und ges. Kochsalzlösung gewaschen. Die org. Phase wird getrocknet, eingeengt und der erhaltene 2-(N-Methyl-2-phenyl-2- oxoacetamido)essigsäuremethylester (Rohausbeute 5.4 g, 23 mmol, 77%) direkt in die nächste Stufe eingesetzt. Dazu erhitzt man den Rückstand mit 20 ml  Sodium bicarbonate solution and sat. Washed saline. The org. Phase is dried, concentrated and the resulting 2- (N-methyl-2-phenyl-2-oxoacetamido) acetic acid methyl ester (crude yield 5.4 g, 23 mmol, 77%) used directly in the next stage. For this, the residue is heated with 20 ml
Dimethylformamiddimethylacetal unter Rückfluss für 6 h. Anschließend engt man am Vakuum ein, löst den erhaltenen 2-(N-Methl-2-phenyl-2-oxoacetamido)-3- (dimethylamino)-acrylsäuremethylester in 50 ml Essigsäure, versetzt mit 5.3 g (69 mmol) Ammoniumacetat und erhitzt 3h unter Rückfluss. Die Mischung wird Dimethylformamide dimethyl acetal at reflux for 6 h. Then concentrated on a vacuum, the resulting 2- (N-methyl-2-phenyl-2-oxoacetamido) -3- (dimethylamino) -acrylic acid methyl ester in 50 ml of acetic acid, treated with 5.3 g (69 mmol) of ammonium acetate and heated for 3h under reflux. The mixture will
anschließend am Rotationsverdampfer eingeengt, mit Wasser versetzt und mit Essigester extrahiert. Die organische Phase wird mit ges. then concentrated on a rotary evaporator, mixed with water and extracted with ethyl acetate. The organic phase is washed with sat.
Natriumhydrogencarbonatlösung neutral gewaschen, mit ges. Kochsalzlösung gewaschen, getrocknet, eingeengt und der Rückstand über FC (Heptan/EE) gereinigt. Ausbeute 3.8 g (68%) des 1 -Methyl-3-phenyl-pyrazin-2-on-6- carbonsäuremethylesters. 486 mg (2 mmol) 1 -Methyl-3-phenyl-pyrazin-2-on-6-carbonsäuremethylester und 2 ml Natronlauge (2M, 4 mmol) werden in 4 ml Methanol bei 0°C 30 min gerührt. Sodium bicarbonate solution washed neutral, with sat. Washed brine, dried, concentrated and the residue over FC (heptane / EE). Yield 3.8 g (68%) of the 1-methyl-3-phenyl-pyrazine-2-one-6-carboxylic acid methyl ester. 486 mg (2 mmol) of methyl 1-methyl-3-phenylpyrazine-2-one-6-carboxylate and 2 ml of sodium hydroxide solution (2M, 4 mmol) are stirred in 4 ml of methanol at 0 ° C. for 30 min.
Anschließend wird mit ges. Ammoniumchloridlösung versetzt, die Kristalle abgesaugt und gewaschen. Ausbeute 435 mg (95%). Subsequently, with ges. Ammonium chloride solution, the crystals are filtered off and washed. Yield 435 mg (95%).
Zu 229 mg (1 .0 mmol) 1 -Methyl-3-phenyl-pyrazin-2-on-6-carbonsäure und 149 mg (1 .5 mmol) 1 -Methyl-5-aminotetrazol in 3 ml Pyridin werden bei 0°C 155 mg (1 .3 mmol) Thionylchlorid gegeben. Das Gemisch wird 16 h bei RT gerührt. Anschließend wird mit wenig Wasser gequenscht, die ausgefallenen Kristalle abgesaugt und mit wenig Wasser gewaschen. Ausbeute 283 mg (91 %). To 229 mg (1 .0 mmol) of 1-methyl-3-phenylpyrazine-2-one-6-carboxylic acid and 149 mg (1 .5 mmol) of 1-methyl-5-aminotetrazole in 3 ml of pyridine are added at 0 ° C, 155 mg (1. 3 mmol) of thionyl chloride. The mixture is stirred at RT for 16 h. The mixture is then quenched with a little water, the precipitated crystals are filtered off with suction and washed with a little water. Yield 283 mg (91%).
Die in nachfolgenden Tabellen aufgeführten Beispiele wurden analog oben genannten Methoden hergestellt beziehungsweise sind analog oben genannten Methoden erhältlich. Diese Verbindungen sind ganz besonders bevorzugt. The examples listed in the following tables were prepared analogously to the above-mentioned methods or are obtainable analogously to the methods mentioned above. These compounds are most preferred.
Die verwendeten Abkürzungen bedeuten: The abbreviations used mean:
Ph = Phenyl Me = Methyl iPr = i-Propyl cPr = Cyclopropyl  Ph = phenyl Me = methyl iPr = i-propyl cPr = cyclopropyl
Tabelle 1 : Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Table 1: Compounds of the invention of the general formula (I) wherein Q is
Q1 steht, und R3 sowie Y jeweils Methyl bedeuten. Q 1 , and R 3 and Y are each methyl.
Figure imgf000032_0001
Figure imgf000032_0001
Nr. X1 X2 Z Physikalische Daten No. X 1 X 2 Z Physical data
( H-NMR, DMSO-d6, 400 MHz) (H-NMR, DMSO-d 6 , 400 MHz)
1-1 N CH H  1-1 N CH H
1-2 N CH Me  1-2 N CH Me
1-3 N CH CF3 1-3 N CH CF 3
1-4 N CH iPr  1-4 N CH iPr
1-5 N CH cPr 11.98 (brs,1 H), 7.67 (s,1 H), 3.96 (s,3H),  1-5 N CH cPr 11.98 (brs, 1H), 7.67 (s, 1H), 3.96 (s, 3H),
3.52 (s,3H), 2.66 (m,1 H), 1.17-1.05 (m,2H), 1.01-0.96 (m,2H)  3.52 (s, 3H), 2.66 (m, 1H), 1.17-1.05 (m, 2H), 1.01-0.96 (m, 2H)
1-6 N CH 2-Propenyl  1-6 N CH 2 -propenyl
1-7 N CH Ph 12.20 (brs,1 H), 8.30 (m,2H), 7.98 (s,1 H), Nr. X1 X2 Z Physikalische Daten 1-7 N CH Ph 12.20 (brs, 1H), 8.30 (m, 2H), 7.98 (s, 1H), No. X 1 X 2 Z Physical data
( H-NMR, DMSO-d6,400 MHz)(H-NMR, DMSO-d 6 , 400 MHz)
7.53-7.48 (m,3H), 4.01 (s,3H), 3.60 (s,3H)-8 N CH 2-CIPh7.53-7.48 (m, 3H), 4.01 (s, 3H), 3.60 (s, 3H) -8N CH 2-CIPh
-9 N CH 3-CIPh-9 N CH 3-CIPh
-10 N CH 4-CIPh-10 N CH 4-CIPh
-11 N CH 3,5-F2Ph 12.27 (brs,1H), 8.06 (m,2H), 8.02 (s,1H), -11 N CH 3,5-F 2 Ph 12.27 (brs, 1H), 8:06 (m, 2H) 8.02 (s, 1H),
7.44 (m,1H), 4.01 (s,3H), 3.61 (s,3H)-12 N CH SMe 12.00 (brs,1H), 7.83 (s,1H), 3.97 (s,3H),  7.44 (m, 1H), 4.01 (s, 3H), 3.61 (s, 3H) -12 N CH SMe 12.00 (brs, 1H), 7.83 (s, 1H), 3.97 (s, 3H),
3.53 (s,3H), 2.44 (s,3H) 3.53 (s, 3H), 2.44 (s, 3H)
-13 N CH SEt-13 N CH SEt
-14 N N CF3-14 N N CF3
-15 N N iPr-15 N N iPr
-16 N N cPr-16 N N cPr
-17 N N 2-Propenyl-17 N N-2-propenyl
-18 N N Ph 12.05 (brs,1H), 8.71 (dd,2H), 7.66 (m,1H), -18 N N Ph 12.05 (brs, 1H), 8.71 (dd, 2H), 7.66 (m, 1H),
7.57 (dd,2H), 3.97 (s,3H), 3.83 (s,3H)-19 N N 2-CIPh 7.57 (dd, 2H), 3.97 (s, 3H), 3.83 (s, 3H) -19 N N 2-CIPh
-20 N N 3-CIPh-20 N N 3-CIPh
-21 N N 4-CIPh-21 N N 4-CIPh
-22 N N 3,5-F2Ph 11.59 (brs,1H), 8.52 (m,2H), 7.60 (m,1H), -22N, 3.5F 2 Ph 11.59 (brs, 1H), 8.52 (m, 2H), 7.60 (m, 1H),
3.96 (s,3H), 3.84 (s,3H) 3.96 (s, 3H), 3.84 (s, 3H)
-23 CMe N CF3-23 CMe N CF3
-24 CMe N iPr-24 CMe N iPr
-25 CMe N cPr-25 CMe N cPr
-26 CMe N 2-Propenyl-26 CMe N 2-propenyl
-27 CMe N Ph 12.05 (brs,1H), 7.46 (dd,2H), 7.39 (t,1H), -27 CMe N Ph 12.05 (brs, 1H), 7.46 (dd, 2H), 7.39 (t, 1H),
7.31 (d,2H), 4.01 (s,3H), 3.58 (s,3H), 2.18 (s,3H) 7.31 (d, 2H), 4.01 (s, 3H), 3.58 (s, 3H), 2.18 (s, 3H)
-28 CMe N 2-CIPh-28 CMe N 2-CIPh
-29 CMe N 3-CIPh-29 CMe N 3-CIPh
-30 CMe N 4-CIPh-30 CMe N 4-CIPh
-31 CMe N 3,5-F2Ph 12.10 (brs,1H), 7.29 (m,1H), 7.10 (m,2H), -31 CMe N 3.5-F 2 Ph 12.10 (brs, 1H), 7.29 (m, 1H), 7.10 (m, 2H),
4.01 (s,3H), 3.58 (s,3H), 2.22 (s,3H)-32 CH N Ph 8.25 (s,1H), 7.76-7.36 (m,5H), 3.99 (s,3H),  4.01 (s, 3H), 3.58 (s, 3H), 2.22 (s, 3H) -32 CH N Ph 8.25 (s, 1H), 7.76-7.36 (m, 5H), 3.99 (s, 3H),
3.65 (s,3H) 3.65 (s, 3H)
-33 CH N CF3 8.57 (s,1H), 3.98 (s,3H), 3.60 (s,3H) Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q1 steht, R3 Methyl bedeutet, Y für Methyl steht, und worin Z und R2 einen Benzolring bilden. -33 CH N CF 3 8.57 (s, 1H), 3.98 (s, 3H), 3.60 (s, 3H) Compounds of the invention of the general formula (I) wherein Q is Q 1 , R 3 is methyl, Y is methyl, and wherein Z and R 2 form a benzene ring.
Figure imgf000034_0001
Figure imgf000034_0001
Nr. Rb1 Rb2 Rb3 Rb4 Physikalische Daten No. R b1 R b2 R b3 R b4 Physical data
( H-NMR, CDCI3,400 MHz)-1 H H H H 8.23 (d,1H), 7.92 (m,1H), 7.81 (m,1H), 7.67 (H-NMR, CDCl 3 , 400 MHz) -1HHHH 8.23 (d, 1H), 7.92 (m, 1H), 7.81 (m, 1H), 7.67
(m,1H), 4.01 (s,3H), 3.63 (s,3H) (m, 1H), 4.01 (s, 3H), 3.63 (s, 3H)
-2 F H H H-2 F H H H
-3 H F H H 10.8 (brs,1H), 8.00 (dd,1H), 7.84 (dd,1H), -3 H F H H 10.8 (brs, 1H), 8.00 (dd, 1H), 7.84 (dd, 1H),
7.58 (ddd,1H), 4.14 (s,3H), 4.00 (s,3H)-4 H H F H 8.38 (dd,1H), 7.45 (dd,1H), 7.37 (ddd,1H),  7.58 (ddd, 1H), 4.14 (s, 3H), 4.00 (s, 3H) -4 H H F H 8.38 (dd, 1H), 7.45 (dd, 1H), 7.37 (ddd, 1H),
4.14 (s,3H), 3.99 (s,3H) 4.14 (s, 3H), 3.99 (s, 3H)
-5 H H H F 10.6 (brs,1H), 8.14 (dd,1H), 7.61-7.51 -5 H H H F 10.6 (brs, 1H), 8.14 (dd, 1H), 7.61-7.51
(m,2H), 4.13 (s,3H), 4.02 (s,3H) (m, 2H), 4.13 (s, 3H), 4.02 (s, 3H)
-6 CF3 H H H 10.7 (brs,1H), 8.03 (d,1H), 7.95-7.92 (m,2H), -6 CF 3 HHH 10.7 (brs, 1H), 8.03 (d, 1H), 7.95-7.92 (m, 2H),
4.14 (s,3H), 4.01 (s,3H) 4.14 (s, 3H), 4.01 (s, 3H)
-7 H CF3 H H-7 H CF 3 HH
-8 H H CF3 H-8 HH CF 3 H
-9 H H H CF3 10.4 (brs,1H), 8.58 (dd,1H), 8.17 (dd,1H), -9HHH CF 3 10.4 (brs, 1H), 8.58 (dd, 1H), 8.17 (dd, 1H),
7.73 (dd,1 H), 4.11 (s,3H), 4.06 (s,3H) 7.73 (dd, 1H), 4.11 (s, 3H), 4.06 (s, 3H)
Tabelle 3: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q5 steht, Rc1 Hydroxy bedeutet, Rc2, Rc3, Rc4, Rc5, Rc6 und Rc7 jeweils Wasserstoff bedeuten, und Y für Methyl. Table 3: Compounds of the invention of the general formula (I) wherein Q is Q 5 , R c1 is hydroxy, R c2 , R c3 , R c4 , R c5 , R c6 and R c7 are each hydrogen, and Y is methyl.
Figure imgf000035_0001
Figure imgf000035_0003
Figure imgf000035_0001
Figure imgf000035_0003
Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q6 steht, Rp1 und Rp3 jeweils Wasserstoff bedeuten, und Rp2 sowie Y jeweils Methyl bedeuten. Compounds of the invention of the general formula (I) wherein Q is Q 6 , R p1 and R p3 are each hydrogen, and R p2 and Y are each methyl.
Figure imgf000035_0002
Figure imgf000035_0002
Nr. X1 X2 Z Physikalische Daten No. X 1 X 2 Z Physical data
( H-NMR, DMSO-d6, 400 MHz) (H-NMR, DMSO-d 6 , 400 MHz)
4-1 N CH Me  4-1 N CH Me
4-2 N CH CF3 4-2 N CH CF 3
4-3 N CH iPr  4-3 N CH iPr
4-4 N CH cPr  4-4 N CH cPr
4-5 N CH Ph 8.33-8.30 (m,2H), 7.79 (s,1 H), 7.59 (s,1 H),  4-5N CH Ph 8.33-8.30 (m, 2H), 7.79 (s, 1H), 7.59 (s, 1H),
7.50-7.46 (m,3H), 3.55 (s,3H), 3.45 (s,3H) Tabelle 5: Verbindungen der allgemeinen Formel (IV), worin Y Methyl bedeutet, worin R6 für R7 steht, sowie Verbindungen der allgemeinen Formel (III), worin R6 und W jeweils für Wasserstoff stehen. 7.50-7.46 (m, 3H), 3.55 (s, 3H), 3.45 (s, 3H) Table 5: Compounds of general formula (IV), wherein Y is methyl, wherein R 6 is R 7 , and compounds of general formula (III), wherein R 6 and W are each hydrogen.
Figure imgf000036_0001
Figure imgf000036_0002
Figure imgf000036_0001
Figure imgf000036_0002
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 inert material 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. ) 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 potassium lignosulfonate and 1 part by weight of oleoylmethyltaurine sodium as wetting and dispersing agent and ground in a pin mill. A dispersion concentrate readily dispersible in water is obtained by reacting 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,  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) Ein emulgierbares Konzentrat wird erhalten aus 15 Gew.-Teilen einer 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 the 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. f) Ein in Wasser dispergierbares Granulat wird auch erhalten, indem man  milled, ground on a pin mill and granulated the powder in a fluidized bed by spraying water as Granulierflüssigkeit. f) A water-dispersible granules are 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 weight of 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 of calcium carbonate and
50 Gew.-Teile Wasser  50 parts by weight of water
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.  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 Samen von mono- bzw. dikotylen Unkraut und Kulturpflanzen werden in Holzfasertöpfen 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. Emulsion unter Zusatz von 0,5% Additiv mit einer Wasseraufwandmenge von umgerechnet 600 l/ha auf die Oberfläche der Abdeckerde appliziert. 1 . Herbicidal action against weevils in pre-emergence Seeds of monocotyledonous or dicotyledonous weeds and crops are laid out in wood fiber pots and covered with soil. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the cover soil as an aqueous suspension or emulsion with the addition of 0.5% of additive at a water application rate of 600 l / ha.
Nach der Behandlung werden die Töpfe im Gewächshaus aufgestellt und unter guten Wachstumsbedingungen für die Testpflanzen gehalten. Nach ca. 3 Wochen wird die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen in  After the treatment, the pots are placed in the greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect of the preparations is visually compared to untreated controls in
Prozentwerten bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie Kontrollpflanzen. Beispielsweise zeigten dabei die Verbindungen Nr. 1 -27, 1 -31 , 1 -33, 2-3, 2-6 und 2-8 bei einer Aufwandmenge von 0,32 kg Aktivsubstanz oder weniger pro Hektar eine sehr gute Wirkung (80% bis 100% herbizide Wirkung) gegen Schadpflanzen wie Amaranthus retroflexus. Gleichzeitig lassen erfindungsgemäße Verbindungen Gramineenkulturen wie Gerste, Weizen, Roggen, Hirse, Mais oder Reis im Vorauflaufverfahren selbst bei hohen Scores percentages. For example, 100% means action = plants are dead, 0% effect = like control plants. For example, compounds Nos. 1 -27, 1 -31, 1 -33, 2-3, 2-6 and 2-8 showed a very good effect at an application rate of 0.32 kg of active ingredient or less per hectare (80%). up to 100% herbicidal action) against harmful plants such as Amaranthus retroflexus. At the same time, compounds according to the invention leave gramineous crops such as barley, wheat, rye, millet, maize or rice in the pre-emergence process even at high temperatures
Wirkstoffdosierungen praktisch ungeschädigt. Einige Substanzen schonen darüber hinaus auch zweikeimblättrige Kulturen wie Soja, Baumwolle, Raps, Zuckerrüben oder Kartoffeln. Die erfindungsgemäßen Verbindungen zeigen teilweise eine hohe Active ingredient doses virtually undamaged. In addition, some substances also protect dicotyledonous crops such as soya, cotton, rapeseed, sugar beet or potatoes. Some of the compounds of the invention show a high level
Selektivität und eignen sich deshalb im Vorauflaufverfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs in landwirtschaftlichen Kulturen. Selectivity and are therefore suitable in the pre-emergence process for controlling undesirable plant growth in agricultural crops.
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 Gewächshaus unter kontrollierten Wachstumsbedingungen angezogen. 2 bis 3 Wochen nach der Aussaat werden die Versuchspflanzen im Einblattstadium Wood fiber pots laid in sandy loam soil, covered with soil and grown in the greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants are in the single leaf stage
behandelt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen werden dann als wässrige Suspension bzw. Emulsion unter Zusatz von 0,5% Additiv mit einer treated. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then treated with an aqueous suspension or emulsion with addition of 0.5% of additive
Wasseraufwandmenge von umgerechnet 600 l/ha auf die grünen Pflanzenteile gesprüht. Nach ca. 3 Wochen Standzeit der Versuchspflanzen im Gewächshaus unter optimalen Wachstumsbedingungen wird die Wirkung der Präparate visuell im  Water application amount of 600 l / ha sprayed on the green parts of plants. After about 3 weeks life of the test plants in the greenhouse under optimal growth conditions, the effect of the preparations is visually in
Vergleich zu unbehandelten Kontrollen bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie Kontrollpflanzen. Compared to untreated controls scored. For example, 100% means Effect = plants have died, 0% effect = like control plants.
Beispielsweise zeigten dabei die Verbindungen Nr. 1 -27, 1 -31 , 1 -33, 2-3, 2-4 und 2-5 bei einer Aufwand-menge von 0,32 kg Aktivsubstanz oder weniger pro Hektar eine sehr gute herbizide Wirkung (80% bis 100% herbizide Wirkung) gegen Schadpflanzen wie Pharbitis purpureum, und beispielsweise die Verbindungen Nr. 1 -5, 1 -27, 1 -33 und 2-6 gegen Schadpflanzen wie Echinochloa crus-galli und Stellaria media. Gleichzeitig lassen erfindungsgemäße Verbindungen Gramineenkulturen wie Gerste, Weizen, Roggen, Hirse, Mais oder Reis im Nachauflaufverfahren selbst bei hohen For example, the compounds Nos. 1-27, 1-31, 1-33, 2-3, 2-4 and 2-5 showed a very good herbicidal action at a cost of 0.32 kg of active ingredient or less per hectare (80% to 100% herbicidal activity) against harmful plants such as Pharbitis purpureum, and for example, the compounds Nos. 1-5, 1 -27, 1 -33 and 2-6 against harmful plants such as Echinochloa crus-galli and Stellaria media. At the same time, compounds according to the invention leave gramineous crops such as barley, wheat, rye, millet, maize or rice in postemergence even at high levels
Wirkstoffdosierungen praktisch ungeschädigt. Einige Substanzen schonen darüber hinaus auch zweikeimblattrige Kulturen wie Soja, Baumwolle, Raps, Zuckerrüben oder Kartoffeln. Die erfindungs-gemäßen Verbindungen zeigen teilweise eine hohe Active ingredient doses virtually undamaged. In addition, some substances also protect dicotyledonous crops such as soybeans, cotton, canola, sugar beet or potatoes. Some of the compounds according to the invention show a high level
Selektivität und eignen sich deshalb im Nachauflaufverfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs in landwirtschaftlichen Kulturen. Selectivity and are therefore suitable postemergence for combating undesirable plant growth in agricultural crops.

Claims

Patentansprüche BCS13-1012 Patent claims BCS13-1012
1 . 6-Azinon-2-carbonyl-derivate der Formel (I) oder deren Salze 1 . 6-Azinone-2-carbonyl derivatives of the formula (I) or their salts
Figure imgf000040_0001
worin die Substituenten folgende Bedeutungen haben
Figure imgf000040_0001
in which the substituents have the following meanings
Q bedeutet einen Rest Q1, Q2, Q3, Q4, Q5, Q6, Q7 oder Q8, Q means a residue Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , Q 7 or Q 8 ,
Figure imgf000040_0002
Figure imgf000040_0002
Q CT Cf
Figure imgf000040_0003
 QCT Cf
Figure imgf000040_0003
Q5 Q6 Q7 Q8 Q5 Q6 Q7 Q8
R3 bedeutet (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, wobei diese Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Hydroxy, Nitro, SiR10 3, PO(OR10)2, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, COR3a, COOR3a, OCOR3a, NR3aCOR3a, NR3aSO2R3b, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocyclyl oder Phenyl substituiert sind, wobei die 4 letztgenannten Reste jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluornnethyl, Cyano und Halogen substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, oder R 3 means (Ci-C 8 )-alkyl, (C 2 -C 8 )-alkenyl, (C 2 -C 8 )-alkynyl, where these radicals are each replaced by s radicals from the group consisting of halogen, cyano, hydroxy, Nitro, SiR 10 3 , PO(OR 10 ) 2 , S(O) n -(Ci-C 6 )-alkyl, (Ci-C 6 )-alkoxy, halogen-(Ci-C 6 )-alkoxy, COR 3a , COOR 3a , OCOR 3a , NR 3a COR 3a , NR 3a SO 2 R 3b , (C 3 -C 6 )-cycloalkyl, heteroaryl, heterocyclyl or phenyl are substituted, the last 4 radicals each being substituted by p radicals from the group are substituted from methyl, ethyl, methoxy, trifluoronethyl, cyano and halogen, and where heterocyclyl n carries oxo groups, or
R3 bedeutet durch p Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C4)-alkyl substituiertes Phenyl, R3a bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl oder (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R3b bedeutet (Ci-C6)-Alkyl, (C2-C6)-Alkenyl oder (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl oder (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 3 through p means radicals from the group consisting of halogen, nitro, cyano, (Ci-C 6 )-alkyl, halogen-(Ci-C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O ) n -(Ci-C 6 )-alkyl, (Ci-C 6 )-alkoxy, halogen-(Ci-C6)-alkoxy, (Ci-C6)-alkoxy-(Ci-C 4 )-alkyl substituted phenyl, R 3a means hydrogen, (Ci-C 6 )-alkyl, (C2-C 6 )-alkenyl, (C2-C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl or (C3-C6)-cycloalkyl- (Ci-C6)-alkyl or phenyl, R 3b means (Ci-C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C2-C 6 )-alkynyl, (C3-C 6 )-cycloalkyl or (C3-C6)-cycloalkyl-(Ci-C 6 )-alkyl or phenyl,
R4 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C3-C7)-cyclo-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (C2-C6)-Alkenyl, (C2-C6)-Alkenyloxy, (C2-C6)- Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Alkinyloxy, (C2-C6)-Halogenalkinyl, (Ci-C6)- Alkoxy-(Ci-C6)-Alkyl, Cyano, Nitro, Methylsulfenyl, Methylsulfinyl, Methylsulfonyl, Acetylamino, Benzoylamino, Methoxycarbonyl, Ethoxycarbonyl, R 4 means hydrogen, (Ci-C 6 )-alkyl, (C 3 -C 7 )-cyclo-alkyl, halogen-(Ci-C 6 )-alkyl, (Ci-Ce)-alkoxy, halogen-(Ci- C 6 )-alkoxy, (C2-C 6 )-alkenyl, (C2-C 6 )-alkenyloxy, (C 2 -C 6 )-haloalkenyl, (C2-C 6 )-alkynyl, (C2-C 6 )- Alkynyloxy, (C2- C6 )-haloalkynyl, (Ci- C6 )-alkoxy-(Ci-C6)-alkyl, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl,
Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Benzoyl, Methylcarbonyl, Methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl,
Piperidinylcarbonyl, Trifluormethylcarbonyl, Halogen, Amino, Aminocarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl,
Methylaminocarbonyl, Dimethylanninocarbonyl, Methoxymethyl, Methylaminocarbonyl, dimethylanninocarbonyl, methoxymethyl,
oder jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl und Halogen substituiertes Heteroaryl, Heterocyclyl oder Phenyl, or heteroaryl, heterocyclyl or phenyl substituted by p radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,
R5 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-Alkyl, CH2R5a, (C3- C7)-Cycloalkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2- Ce)-Alkinyl, Halogen-(C2-C6)-alkinyl, OR6, NHR6, Methoxycarbonyl, Ethoxycarbonyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Methylcarbonyl, R 5 means hydrogen, (Ci-C 6 )-alkyl, (Ci-C 6 )-alkoxy-(Ci-C 6 )-alkyl, CH 2 R 5a , (C 3 - C 7 )-cycloalkyl, halogen-( Ci-C 6 )-alkyl, (C2-C 6 )-alkenyl, halogen-(C2-C 6 )-alkenyl, (C 2 - Ce)-alkynyl, halogen-(C2-C6)-alkynyl, OR 6 , NHR 6 , methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methylcarbonyl,
Trifluormethylcarbonyl, Dimethylamino, Acetylamino, Methylsulfenyl, Methylsulfinyl, Methylsulfonyl oder jeweils durch p Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C )-alkyl Trifluoromethylcarbonyl, dimethylamino, acetylamino, methylsulfenyl, methylsulfinyl, methylsulfonyl or in each case p radicals from the group consisting of halogen, nitro, cyano, (Ci-C 6 )-alkyl, halogen-(Ci-C 6 )-alkyl, (C3- C 6 )-cycloalkyl, S(O) n -(Ci-C 6 )-alkyl, (Ci-Ce)-alkoxy, halogen-(Ci-C 6 )-alkoxy, (Ci-C 6 )-alkoxy-( Ci-C )-alkyl
substituiertes Heteroaryl, Heterocyclyl, Benzyl oder Phenyl, substituted heteroaryl, heterocyclyl, benzyl or phenyl,
R5a bedeutet Acetoxy, Acetamido, N-Methylacetamido, Benzoyloxy, Benzamido, N- Methylbenzamido, Methoxycarbonyl, Ethoxycarbonyl, Benzoyl, Methylcarbonyl, Piperidinylcarbonyl, Morpholinylcarbonyl, Trifluormethylcarbonyl, Aminocarbonyl, Methylaminocarbonyl, Dimethylaminocarbonyl, (Ci-C6)-Alkoxy, (C3-C6)-Cycloalkyl oder jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, R 5a means acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, (Ci-C6)-alkoxy, (C3- C6)-cycloalkyl or in each case p radicals from the group consisting of methyl, ethyl, methoxy,
Trifluormethyl und Halogen substituiertes Heteroaryl oder Heterocyclyl, W bedeutet O, CO oder CRc6Rc7, Rc1 bedeutet Hydroxy oder SR11 , trifluoromethyl and halogen substituted heteroaryl or heterocyclyl, W means O, CO or CR c6 R c7 , R c1 means hydroxy or SR 11 ,
Rc2 und Rc5 bedeuten unabhängig voneinander jeweils Wasserstoff oder (Ci-C4)- Alkyl, oder R c2 and R c5 each independently represent hydrogen or (Ci-C 4 )-alkyl, or
Rc2 und Rc5 bilden gemeinsam eine Ethylen- oder Vinylengruppe, Rc3, Rc4, Rc6 und Rc7 bedeuten unabhängig voneinander jeweils Wasserstoff oder (Ci- C4)-Alkyl, R c2 and R c5 together form an ethylene or vinylene group, R c3 , R c4 , R c6 and R c7 each independently represent hydrogen or (Ci- C4 )-alkyl,
RP1 bedeutet Wasserstoff, (Ci-C6)-Alkylsulfonyl, (Ci-C )-Alkoxy-(Ci-C6)- alkylsulfonyl, oder jeweils durch m gleiche oder verschiedene Reste aus der Gruppe bestehend aus Halogen, (Ci-C4)-Alkyl und (Ci-C4)-Alkoxy substituiertes RP 1 means hydrogen, (Ci-C 6 )-alkylsulfonyl, (Ci-C )-alkoxy-(Ci-C 6 )-alkylsulfonyl, or each replaced by m identical or different radicals from the group consisting of halogen, (Ci-C 4 )-alkyl and (Ci-C 4 )-alkoxy substituted
Phenylsulfonyl, Thiophenyl-2-sulfonyl, Benzoyl, Benzoyl-(Ci-C6)-alkyl oder Benzyl, Phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(Ci-C6)-alkyl or benzyl,
Rp2 bedeutet (Ci-C4)-Alkyl, RP3 bedeutet Wasserstoff, (Ci-C4)-Alkyl, (C3-C8)-Cycloalkyl, (Ci-C4)-Alkyl-(C3-C8)- cycloalkyl, (C3-C6)-Halogencycloalkyl, R p2 means (Ci-C 4 )-alkyl, RP 3 means hydrogen, (Ci-C 4 )-alkyl, (C 3 -C 8 )-cycloalkyl, (Ci-C 4 )-alkyl-(C 3 -C 8 )-cycloalkyl, (C3-C6)-halocycloalkyl,
Rn1 bedeutet (Ci-C )-Alkyl, (C3-C8)-Cycloalkyl, (Ci-C )-Alkyl-(C3-C8)-cycloalkyl, (C3- C6)-Halogencycloalkyl, R n1 means (Ci-C )-alkyl, (C 3 -C 8 )-cycloalkyl, (Ci-C )-alkyl-(C 3 -C 8 )-cycloalkyl, (C 3 - C6)-halocycloalkyl,
Rn2 bedeutet Wasserstoff, CO2(Ci-C6)-Alkyl oder S(O)n(Ci-C6)-Alkyl, X1 bedeutet N oder CR2, R n2 means hydrogen, CO 2 (Ci-C 6 )-alkyl or S(O) n (Ci-C 6 )-alkyl, X 1 means N or CR 2 ,
X2 bedeutet N oder CH, X 2 means N or CH,
mit der Maßgabe, dass mindestens einer der beiden Reste X1 und X2 N bedeutet, with the proviso that at least one of the two radicals X 1 and X 2 means N,
R2 bedeutet Wasserstoff, Halogen, Cyano, Nitro, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (C2-C6)-Alkenyl, (C2-C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3- C6)-Cycloalkyl, (Cs-CeJ-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, (Ci-C )-Alkoxy oder (Ci-C )-Haloalkoxy, R 2 means hydrogen, halogen, cyano, nitro, (Ci-C )-alkyl, (Ci-C )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 3 - C 6 )-cycloalkyl, (Cs-CeJ-halocycloalkyl, (Ci-C6)-alkyl-O-(Ci-C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl-(Ci-C 6 )-alkyl , (Ci-C)-alkoxy or (Ci-C)-haloalkoxy,
Y 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, Halogen-(C3-C6)- cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, OCOOR6, OC(O)N(R6)2, OR6, OCOR6, OSO2R7, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl- OR6, (Ci-C6)-Alkyl-OCOR6, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl- SO2OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-CN, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)- Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR6SO2R7, CH2P(O)(OR10)2, (Ci-C6)-Alkyl-Aryl, (Ci-C6)- Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, wobei die drei letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, (C1-C6)- Alkyl, Halogen-(Ci-C6)-alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-Ce)- alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Y means (Ci-C 6 )-alkyl, halogen-(Ci-C 6 )-alkyl, (C2-C 6 )-alkenyl, halogen-(C 2 -C 6 )-alkenyl, (C2-C 6 )- Alkynyl, halo-(C3-C 6 )-alkynyl, (C3-C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-C 6 )-alkyl , halogen-(C3-C6)-cycloalkyl-(Ci-C 6 )-alkyl, OCOOR 6 , OC(O)N(R 6 ) 2 , OR 6 , OCOR 6 , OSO 2 R 7 , (Ci-C 6 )-Alkyl-S(O) n R 7 , (Ci-C 6 )-Alkyl-OR 6 , (Ci-C 6 )-Alkyl-OCOR 6 , (Ci-C 6 )-Alkyl-OSO 2 R 7 , (Ci-C 6 )-Alkyl-CO 2 R 6 , (Ci-C 6 )-Alkyl-SO 2 OR 6 , (Ci-C 6 )-Alkyl-CON(R 6 ) 2 , (Ci-C 6 ) -Alkyl-CN, (Ci-C 6 )-Alkyl-SO 2 N(R 6 ) 2 , (Ci-C 6 )-Alkyl-NR 6 COR 6 , (Ci-C 6 )-Alkyl-NR 6 SO 2 R 7 , CH 2 P(O)(OR 10 ) 2 , (Ci-C 6 )-alkyl-aryl, (Ci-C 6 )-alkyl-heteroaryl, (Ci-C6)-alkyl-heterocyclyl, where the three The latter radicals are each replaced by s radicals from the group consisting of halogen, cyano, nitro, (C1-C6)-alkyl, halogen-(Ci-C 6 )-alkyl, S(O) n -(Ci-C 6 )-alkyl , (Ci-Ce)-alkoxy, halogen-(Ci-Ce)-alkoxy are substituted, and where heterocyclyl carries n oxo groups,
Z bedeutet Wasserstoff, Halogen, Cyano, Rhodano, Nitro, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2- C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (Ci-C6)-alkyl-(C3-C6)- cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR6, COOR6, OR6, OCOOR6, NR6COOR6, C(O)N(R6)2, NR6C(O)N(R6)2, Z means hydrogen, halogen, cyano, rhodano, nitro, (Ci-C6)-alkyl, halogen-(Ci-C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halogen-(C 2 -C 6 ) -alkenyl, (C 2 -C 6 )-alkynyl, halogen-(C 2 - C 6 )-alkynyl, (C3-C 6 )-cycloalkyl, halogen-(C3-C 6 )-cycloalkyl, (Ci-C6) -alkyl-(C3-C 6 )-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-C 6 )-alkyl, halogen-(C3-C6)-cycloalkyl-(Ci-C 6 )-alkyl, COR 6 , COOR 6 , OR 6 , OCOOR 6 , NR 6 COOR 6 , C(O)N(R 6 ) 2 , NR 6 C(O)N(R 6 ) 2 ,
OC(O)N(R6)2, C(O)NR6OR6, OSO2R7, S(O)nR7, SO2OR6, SO2N(R6)2, NR6SO2R7, NR6COR6, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)- Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR1SO2R7, N(R6)2, P(O)(OR10)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die drei letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)- Alkoxy oder Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n OC(O)N(R 6 ) 2 , C(O)NR 6 OR 6 , OSO 2 R 7 , S(O) n R 7 , SO 2 OR 6 , SO 2 N(R 6 ) 2 , NR 6 SO 2 R 7 , NR 6 COR 6 , (Ci-C 6 )-alkyl-S(O) n R 7 , (Ci-C 6 )-alkyl-OR 6 , (Ci-C 6 )-alkyl-OCOR 1 , (Ci-C 6 )-Alkyl-OSO 2 R 7 , (Ci-C 6 )-Alkyl-CO 2 R 6 , (Ci-C 6 )-Alkyl-SO 2 OR 6 , (Ci-C 6 )-Alkyl -CON(R 6 ) 2 , (Ci-C 6 )-alkyl-SO 2 N(R 6 ) 2 , (Ci-C 6 )-alkyl-NR 6 COR 6 , (Ci-C 6 )-alkyl-NR 1 SO 2 R 7 , N(R 6 ) 2 , P(O)(OR 10 ) 2 , heteroaryl, heterocyclyl or phenyl, where the last three radicals are each replaced by s radicals from the group consisting of halogen, nitro, cyano, ( Ci-C 6 )-alkyl, halogen-(Ci-C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n -(Ci-C 6 )-alkyl, (Ci-C 6 ) - Alkoxy or halogen-(Ci-C6)-alkoxy are substituted, and where heterocyclyl n
Oxogruppen trägt, oder carries oxo groups, or
Z und R2 bilden gemeinsam mit den beiden Kohlenstoffatomen, an denen sie gebunden sind, einen fünf- oder sechsgliedrigen Ring bestehend aus t Z and R 2 together with the two carbon atoms to which they are bonded form a five- or six-membered ring consisting of t
Kohlenstoffatomen und p Heteroatomen aus der Gruppe bestehend aus N, O und S, wobei dieser Ring durch q Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C6)-alkyl substituiert ist, R6 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C2- C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkenyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-Ce)-Alkyl- Heteroaryl, Heterocycl, (Ci-C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)- Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR8-Heteroaryl, (Ci-C6)-Alkyl-NR8-Heterocyclyl wobei die 21 letztgenannten Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C4)-Alkoxy-(C2-C6)- alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, carbon atoms and p heteroatoms from the group consisting of N, O and S, this ring being replaced by q radicals from the group consisting of halogen, nitro, Cyano, (Ci-C 6 )-alkyl, halo-(Ci-C 6 )-alkyl, (C3-C 6 )-cycloalkyl, S(O) n -(Ci-C 6 )-alkyl, (Ci-C6 )-alkoxy, halogen-(Ci-C6)-alkoxy and (Ci-C6)-alkoxy-(Ci-C6)-alkyl is substituted, R 6 means hydrogen, (Ci-C 6 )-alkyl, (Ci-C 6 )-Haloalkyl, (C2-C 6 )-alkenyl, (C 2 - C 6 )-haloalkenyl, (C2-C 6 )-alkynyl, (C2-C 6 )-haloalkynyl, (C3-C 6 )-cycloalkyl , (C 3 - C 6 )-cycloalkenyl, (C3-C 6 )-halocycloalkyl, (Ci-C6)-alkyl-O-(Ci-C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl-( Ci-C 6 )-alkyl, phenyl, phenyl-(Ci-C 6 )-alkyl, heteroaryl, (Ci-Ce)-alkyl-heteroaryl, heterocyclic, (Ci-C 6 )-alkyl-heterocyclyl, (Ci-C 6 )-Alkyl-O-Heteroaryl, (Ci-C 6 )-Alkyl-O-Heterocyclyl, (Ci-C 6 )-Alkyl-NR 8 -Heteroaryl, (Ci-C 6 )-Alkyl-NR 8 -Heterocyclyl where the latter 21 residues are replaced by s residues from the group consisting of cyano, halogen, nitro, rhodano, OR 8 , S(O) n R 9 , N(R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO2R 9 , CO 2 R 8 , COSR 9 , CON(R 8 ) 2 and (Ci-C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl are substituted, and where Heterocyclyl n carries oxo groups,
R7 bedeutet (Ci -C6)-Al kyl , (C2-C6)-Al kenyl , (C2-C6)-Al kinyl , (C3-C6)-Cycloal kyl , (C3- C6)-Cycloalkenyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (Ci- C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)-Alkyl-O-Heterocyclyl, (Ci- C6)-Alkyl-NR3-Heteroaryl, (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei diese 17 Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C )-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R 7 means (Ci -C 6 )-alkyl, (C 2 -C 6 )-al kenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 - C 6 )-cycloalkenyl, (Ci-C6)-alkyl-O-(Ci-C 6 )-alkyl, (C3-C6)-cycloalkyl-(Ci-C 6 )-alkyl, phenyl, phenyl-(Ci-C6 )-alkyl, heteroaryl, (Ci-C6)-alkyl-heteroaryl, heterocyclyl, (Ci-C 6 )-alkyl-heterocyclyl, (Ci-C 6 )-alkyl-O-heteroaryl, (Ci-C 6 )-alkyl -O-Heterocyclyl, (Ci-C 6 )-Alkyl-NR 3 -Heteroaryl, (Ci-C 6 )-Alkyl-NR 3 -Heterocyclyl, where these 17 residues are replaced by s residues from the group consisting of cyano, halogen, nitro , Rhodano, OR 8 , S(O) n R 9 , N(R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON(R 8 ) 2 and (Ci-C )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl are substituted, and where heterocyclyl n carries oxo groups,
R8 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 8 means hydrogen, (Ci-C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C3-C6) -Cycloalkyl-(Ci-C 6 )alkyl or phenyl,
R9 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Al kinyl oder Phenyl, R 9 means (Ci-C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl or phenyl,
R10 bedeutet (Ci-C4)-Alkyl, R11 bedeutet (Ci-C4)-Alkyl oder durch p Reste aus der Gruppe Halogen, Nitro, Cyano, (Ci-C )-Alkyl, (Ci-C )-Halogenalkyl, (Ci-C )-Alkoxy und (Ci-C )-Halogenalkoxy substituiertes Phenyl, bedeutet 0, 1 oder 2, p bedeutet 0, 1 , 2 oder 3, q bedeutet 0, 1 , 2, 3 oder 4, s bedeutet 0, 1 , 2, 3, 4 oder 5, t bedeutet e 1 , 2, 3, 4, 5 oder 6. R 10 means (Ci-C 4 )alkyl, R 11 means (Ci-C 4 )-alkyl or p radicals from the group halogen, nitro, cyano, (Ci-C )-alkyl, (Ci-C )-haloalkyl, (Ci-C )-alkoxy and (Ci -C )-haloalkoxy substituted phenyl, means 0, 1 or 2, p means 0, 1, 2 or 3, q means 0, 1, 2, 3 or 4, s means 0, 1, 2, 3, 4 or 5 , t means e 1 , 2, 3, 4, 5 or 6.
2. 6-Azinon-2-carbonyl-derivate der Formel (I) oder deren Salze nach Anspruch 1 , worin 2. 6-azinone-2-carbonyl derivatives of the formula (I) or their salts according to claim 1, wherein
Q bedeutet einen Rest Q1, Q2, Q3, Q4, Q5, Q6, Q7 oder Q8, Q means a residue Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , Q 7 or Q 8 ,
Figure imgf000045_0001
Figure imgf000045_0001
Q5 Q6 Q7 Q8 Q5 Q6 Q7 Q8
R3 bedeutet (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, wobei diese Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, S(O)n- (Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocyclyl oder Phenyl substituiert sind, wobei die 4 letztgenannten Reste jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl, Cyano und Halogen substituiert sind, und wobei Heterocydyl n Oxogruppen trägt, oder R3 bedeutet durch p Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy und (Ci-C6)-Alkoxy-(Ci-C4)-alkyl substituiertes Phenyl, R 3 means (Ci-C 8 )-alkyl, (C 2 -C 8 )-alkenyl, (C 2 -C 8 )-alkynyl, where these radicals are each replaced by s radicals from the group consisting of halogen, cyano, nitro, S(O) n - (Ci-C 6 )-alkyl, (Ci-Ce)-alkoxy, halogen-(Ci-C 6 )-alkoxy, (C3-C 6 )-cycloalkyl, heteroaryl, heterocyclyl or phenyl are substituted , with the latter 4 residues respectively are substituted by p radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and where heterocydyl n carries oxo groups, or R 3 means by p radicals from the group consisting of halogen, nitro, cyano, (Ci- C 6 )-alkyl, halo-(Ci-C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n -(Ci-C 6 )-alkyl, (Ci-C 6 )-alkoxy , halogen-(Ci-C6)-alkoxy and (Ci-C6)-alkoxy-(Ci-C 4 )-alkyl substituted phenyl,
R4 bedeutet (Ci-C6)-Alkyl, (C3-C7)-cyclo-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy, Cyano, Nitro, Methylsulfenyl, Methylsulfinyl, R 4 means (Ci-C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halogen-(Ci-C 6 )-alkyl, (Ci-C 6 )-alkoxy, halogen-(Ci-C6 )-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl,
Methylsulfonyl, (Ci-C4)-Alkylcarbonylamino, Benzoylamino, Methoxycarbonyl, Methylsulfonyl, (Ci-C 4 )-alkylcarbonylamino, benzoylamino, methoxycarbonyl,
Ethoxycarbonyl, Benzoyl, Phenoxy, Methylcarbonyl, Piperidinylcarbonyl, Ethoxycarbonyl, Benzoyl, Phenoxy, Methylcarbonyl, Piperidinylcarbonyl,
Trifluormethylcarbonyl, Halogen, Amino, Aminocarbonyl, Methylaminocarbonyl, Dimethylanninocarbonyl, Methoxymethyl, 1 ,2,4-Triazol-1 -yl, Pyrazol-1 -yl, 2-Thiophenyl, 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 1 ,2,4-Oxadiazol-3-yl, Benzoxazol-2-yl, 1 - Ethylbenzimidazol-2-yl, Piperidin-1 -yl oder jeweils durch p Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl und Halogen substituiertes Phenyl, Trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylanninocarbonyl, methoxymethyl, 1,2,4-triazol-1-yl, pyrazol-1-yl, 2-thiophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1, 2,4-oxadiazol-3-yl, benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl or phenyl substituted by p radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen ,
R5 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C3-C7)-Cycloalkyl, Halogen-(Ci-C6)-alkyl, (C3-C7)-Cycloalkylmethyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, R 5 means hydrogen, (Ci-C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halogen-(Ci-C 6 )-alkyl, (C3-C 7 )-cycloalkylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,
Acetylmethyl, Methoxymethyl, Methoxyethyl, Benzyl, Pyrazin-2-yl, Furan-2-yl, Acetylmethyl, Methoxymethyl, Methoxyethyl, Benzyl, Pyrazin-2-yl, Furan-2-yl,
Tetrahydrofuran-2-yl, Morpholin, Dimethylamino oder durch p Reste aus der Gruppe bestehend aus Methyl, Methoxy, Trifluormethyl und Halogen substituiertes Phenyl, Tetrahydrofuran-2-yl, morpholine, dimethylamino or phenyl substituted by p radicals from the group consisting of methyl, methoxy, trifluoromethyl and halogen,
W bedeutet O, CO oder CRc6Rc7, W means O, CO or CR c6 R c7 ,
Rc1 bedeutet Hydroxy, R c1 means hydroxy,
Rc2 und Rc5 bedeuten unabhängig voneinander jeweils Wasserstoff oder Methyl, oder Rc2 und Rc5 bilden gemeinsam eine Ethylen- oder Vinylengruppe, R c2 and R c5 each independently represent hydrogen or methyl, or R c2 and R c5 together form an ethylene or vinylene group,
Rc3, Rc4, Rc6 und Rc7 bedeuten unabhängig voneinander jeweils Wasserstoff oder Methyl, bedeutet Wasserstoff, RP2 bedeutet (Ci-C4)-Alkyl, R c3 , R c4 , R c6 and R c7 independently each mean hydrogen or methyl, means hydrogen, R P2 means (Ci-C 4 )-alkyl,
Rp3 bedeutet Wasserstoff, (Ci-C )-Alkyl oder Cycloproyl, R p3 means hydrogen, (Ci-C)-alkyl or cyclopropyl,
Rn1 bedeutet Cycloproyl, R n1 means cyclopropyl,
Rn2 bedeutet Wasserstoff, X1 bedeutet N oder CR2, R n2 means hydrogen, X 1 means N or CR 2 ,
X2 bedeutet N oder CH, X 2 means N or CH,
mit der Maßgabe, dass mindestens einer der beiden Reste X1 und X2 N bedeutet, R2 bedeutet Wasserstoff, Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (C2-C6)- Alkenyl, (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, (Ci-C )-Alkoxy oder (Ci-C )-Haloalkoxy, with the proviso that at least one of the two radicals X 1 and , (C2-C 6 )-alkynyl, (C3-C 6 )-cycloalkyl, (Ci-C6)-alkyl-O-(Ci-C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl-(Ci -C 6 )-alkyl, (Ci-C )-alkoxy or (Ci-C )-haloalkoxy,
Y 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, Halogen-(C3-C6)- cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, OCOOR6, OC(O)N(R6)2, OR6, OCOR6, OSO2R7, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl- OR6, (Ci-C6)-Alkyl-OCOR6, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl- SO2OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR6SO2R7, CH2P(O)(OR10)2, (Ci-C6)-Alkyl-Aryl, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, wobei die drei letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, (Ci-C6)-Alkyl, Halogen-(Ci-Ce)- alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Y means (Ci-C 6 )-alkyl, halogen-(Ci-C 6 )-alkyl, (C2-C 6 )-alkenyl, halogen-(C 2 -C 6 )-alkenyl, (C2-C 6 )- Alkynyl, halo-(C3-C 6 )-alkynyl, (C3-C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-C 6 )-alkyl , halogen-(C3-C6)-cycloalkyl-(Ci-C 6 )-alkyl, OCOOR 6 , OC(O)N(R 6 ) 2 , OR 6 , OCOR 6 , OSO 2 R 7 , (Ci-C 6 )-Alkyl-S(O) n R 7 , (Ci-C 6 )-Alkyl-OR 6 , (Ci-C 6 )-Alkyl-OCOR 6 , (Ci-C 6 )-Alkyl-OSO 2 R 7 , (Ci-C 6 )-Alkyl-CO 2 R 6 , (Ci-C 6 )-Alkyl-SO 2 OR 6 , (Ci-C 6 )-Alkyl-CON(R 6 ) 2 , (Ci-C 6 ) -Alkyl-SO 2 N(R 6 ) 2 , (Ci-C 6 )-Alkyl-NR 6 COR 6 , (Ci-C 6 )-Alkyl-NR 6 SO 2 R 7 , CH 2 P(O)(OR 10 ) 2 , (Ci-C 6 )-alkyl-aryl, (Ci-C 6 )-alkyl-heteroaryl, (Ci-C6)-alkyl-heterocyclyl, where the last three radicals are each replaced by s radicals from the group consisting of Halogen, cyano, nitro, (Ci-C6)-alkyl, halogen-(Ci-Ce)-alkyl, S(O) n -(Ci-C 6 )-alkyl, (Ci-Ce)-alkoxy and halogen-( Ci-C 6 )-alkoxy are substituted, and where heterocyclyl n carries oxo groups,
Z bedeutet Wasserstoff, Halogen, Cyano, Rhodano, Nitro, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2- C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (Cs-CeJ-CycloalkyKCi-Ce)- alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR6, COOR6, OCOOR6, NR6COOR6, C(O)N(R6)2, NR6C(O)N(R6)2, OC(O)N(R6)2, C(O)NR6OR6, OSO2R7, S(O)nR7, SO2OR6, SO2N(R6)2, NR6SO2R7, NR6COR6, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)- Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (Ci- C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl- NR1SO2R7, N(R6)2, P(O)(OR10)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die letzten drei Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-C6)-Alkoxy oder Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Z means hydrogen, halogen, cyano, rhodano, nitro, (Ci-C6)-alkyl, halogen-(Ci-C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halogen-(C 2 -C 6 ) -alkenyl, (C 2 -C 6 )-alkynyl, halogen-(C 2 - C 6 )-alkynyl, (C3-C 6 )-cycloalkyl, halogen-(C3-C 6 )-cycloalkyl, (Cs-CeJ- CycloalkyKCi-Ce)-alkyl, halogen-(C3-C 6 )-cycloalkyl-(Ci-C 6 )-alkyl, COR 6 , COOR 6 , OCOOR 6 , NR 6 COOR 6 , C(O)N(R 6 ) 2 , NR 6 C(O)N(R 6 ) 2 , OC(O)N(R 6 ) 2 , C(O)NR 6 OR 6 , OSO 2 R 7 , p (O) n R 7 , SO 2 OR 6 , SO 2 N(R 6 ) 2 , NR 6 SO 2 R 7 , NR 6 COR 6 , (Ci-C 6 )-alkyl-S(O) n R 7 , (Ci-C 6 )-Alkyl-OR 6 , (Ci-C 6 )-Alkyl-OCOR 1 , (Ci-C 6 )-Alkyl-OSO 2 R 7 , (Ci-C 6 )-Alkyl-CO 2 R 6 , (Ci-C 6 )-Alkyl-SO 2 OR 6 , (Ci-C 6 )-Alkyl-CON(R 6 ) 2 , (Ci-C 6 )-Alkyl-SO 2 N(R 6 ) 2 , (Ci-C 6 )-Alkyl-NR 6 COR 6 , (Ci-C 6 )-Alkyl- NR 1 SO 2 R 7 , N(R 6 ) 2 , P(O)(OR 10 ) 2 , heteroaryl, heterocyclyl or phenyl, where the last three radicals are each replaced by s radicals from the group consisting of halogen, nitro, cyano, (Ci-C 6 )-alkyl, halogen-(Ci-C 6 )-alkyl, (C3-C 6 )- Cycloalkyl, S(O) n -(Ci-C 6 )-alkyl, (Ci-C6)-alkoxy or halogen-(Ci-C6)-alkoxy are substituted, and where
Heterocyclyl n Oxogruppen trägt, Heterocyclyl n carries oxo groups,
Z und R2 bilden gemeinsam mit den beiden Kohlenstoffatomen, an denen sie gebunden sind, einen fünf- oder sechsgliedrigen Ring bestehend aus t Z and R 2 together with the two carbon atoms to which they are bonded form a five- or six-membered ring consisting of t
Kohlenstoffatomen und p Heteroatomen aus der Gruppe bestehend aus N, O und S, wobei dieser Ring durch q Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C )-alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy- methyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert ist, Carbon atoms and p heteroatoms from the group consisting of N, O and S, this ring being replaced by q radicals from the group consisting of halogen, nitro, cyano, (Ci-C 6 )-alkyl, halogen-(Ci-C )-alkyl , S(O) n -(Ci- C6 )-alkyl, (Ci-Ce)-alkoxy-methyl, (Ci-Ce)-alkoxy and halogen-(Ci-C6)-alkoxy is substituted,
R6 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C2- C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkenyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-Ce)-Alkyl- Heteroaryl, Heterocycl, (Ci-C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)- Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR8-Heteroaryl, (Ci-C6)-Alkyl-NR8-Heterocyclyl wobei die 21 letztgenannten Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8,R 6 means hydrogen, (Ci-C 6 )-alkyl, (Ci-C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 ) -Alkynyl, (C 2 -C 6 )-haloalkynyl, (C3-C 6 )-cycloalkyl, (C 3 - C 6 )-cycloalkenyl, (C3-C 6 )-halocycloalkyl, (Ci-C6)-alkyl-O -(Ci-C 6 )-alkyl, (C 3 -C 6 )- cycloalkyl-(Ci-C 6 )-alkyl, phenyl, phenyl-(Ci-C 6 )-alkyl, heteroaryl, (Ci-Ce)- Alkyl-Heteroaryl, Heterocycl, (Ci-C 6 )-Alkyl-Heterocyclyl, (Ci-C 6 )-Alkyl-O-Heteroaryl, (Ci-C 6 )-Alkyl-O-Heterocyclyl, (Ci-C 6 )- Alkyl-NR 8 -Heteroaryl, (Ci-C 6 )-Alkyl-NR 8 -Heterocyclyl, where the last 21 residues are replaced by s residues from the group consisting of cyano, halogen, nitro, rhodano, OR 8 , S(O) n R 9 , N(R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 ,
SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C4)-Alkoxy-(C2-C6)- alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, SCOR 9 , NR 8 COR 8 , NR 8 SO2R 9 , CO 2 R 8 , COSR 9 , CON(R 8 ) 2 and (Ci-C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl are substituted, and where heterocyclyl carries n oxo groups,
R7 bedeutet (Ci -C6)-Al kyl , (C2-C6)-Al kenyl , (C2-C6)-Al kinyl , (C3-C6)-Cycloal kyl , (C3- C6)-Cycloalkenyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl,R 7 means (Ci -C 6 )-alkyl, (C 2 -C 6 )-al kenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 - C 6 )-cycloalkenyl, (Ci-C6)-alkyl-O-(Ci-C 6 )-alkyl, (C3-C6)-cycloalkyl-(Ci-C 6 )-alkyl,
Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (Ci- C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)-Alkyl-O-Heterocyclyl, (Ci- C6)-Alkyl-NR3-Heteroaryl, (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei diese 17 Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C )-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R8 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, Phenyl, phenyl-(Ci-C6)-alkyl, heteroaryl, (Ci-C6)-alkyl-heteroaryl, heterocyclyl, (Ci-C 6 )-alkyl-heterocyclyl, (Ci-C 6 )-alkyl-O-heteroaryl, (Ci-C 6 )-alkyl-O-heterocyclyl, (Ci-C6)-alkyl-NR 3 -heteroaryl, (Ci-C6)-alkyl-NR 3 -heterocyclyl, these 17 residues being replaced by s residues from the group made from cyano, halogen, nitro, rhodano, OR 8 , S(O) n R 9 , N(R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON (R 8 ) 2 and (Ci-C )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl are substituted, and where heterocyclyl n carries oxo groups, R 8 means hydrogen, (Ci-C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-C 6 )-alkyl or phenyl,
R9 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl oder Phenyl, R10 bedeutet (Ci-C4)-Alkyl, n bedeutet 0, 1 oder 2, p bedeutet 0, 1 , 2 oder 3, q bedeutet 0, 1 , 2, 3 oder 4, s bedeutet 0, 1 , 2, 3, 4 oder 5, t bedeutet 0, 1 , 2, 3, 4, 5 oder 6. R 9 means (Ci-C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl or phenyl, R 10 means (Ci-C 4 )-alkyl, n means 0, 1 or 2, p means 0, 1, 2 or 3, q means 0, 1, 2, 3 or 4, s means 0, 1, 2, 3, 4 or 5, t means 0, 1, 2, 3, 4, 5 or 6.
6-Azinon-2-carbonyl-derivate der Formel (I) oder deren Salze nach Anspruch 1 2, worin 6-Azinone-2-carbonyl derivatives of the formula (I) or salts thereof according to claims 1-2, wherein
bedeutet einen Rest Q1, Q2, Q3, Q4, Q5, Q6, Q7 oder Q8, means a residue Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , Q 7 or Q 8 ,
Figure imgf000049_0001
Figure imgf000049_0001
Q1 Q2 Q3 Q4
Figure imgf000050_0001
 Q1 Q2 Q3 Q4
Figure imgf000050_0001
Q5 Q6 Q7 Q8 Q5 Q6 Q7 Q8
R3 bedeutet jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Cyano, Nitro, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiertes (Ci-C8)-Alkyl, (C2-C8)-Alkenyl oder (C2-C8)-Alkinyl, R 3 each represents through s radicals from the group consisting of halogen, cyano, nitro, S(O)n-(Ci-C 6 )-alkyl, (Ci-C 6 )-alkoxy and halogen-(Ci-C 6 ) -alkoxy substituted (Ci-C 8 )-alkyl, (C 2 -C 8 )-alkenyl or (C 2 -C 8 )-alkynyl,
R4 bedeutet (Ci-C6)-Alkyl, (C3-C7)-cyclo-Alkyl, Halogen-(Ci-C6)-alkyl, (Ci-C6)- Alkoxy, Halogen-(Ci-C6)-alkoxy, Cyano, Nitro, Methylsulfenyl, Methylsulfinyl, R 4 means (Ci-C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halogen-(Ci-C 6 )-alkyl, (Ci-C 6 )-alkoxy, halogen-(Ci-C6 )-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl,
Methylsulfonyl, (Ci-C4)-Alkylcarbonylamino, Benzoylamino, Methoxycarbonyl, Methylsulfonyl, (Ci-C 4 )-alkylcarbonylamino, benzoylamino, methoxycarbonyl,
Ethoxycarbonyl, Benzoyl, Phenoxy, Methylcarbonyl, Piperidinylcarbonyl, Ethoxycarbonyl, Benzoyl, Phenoxy, Methylcarbonyl, Piperidinylcarbonyl,
Trifluormethylcarbonyl, Halogen, Amino, Aminocarbonyl, Methylaminocarbonyl, Dimethylanninocarbonyl, Methoxymethyl, 1 ,2,4-Triazol-1 H, 1 -Pyrazol-1 H, 2-Thiophenyl, 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 1 ,2,4-Oxadiazol-3-yl, Benzoxazol-2-yl, Trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylanninocarbonyl, methoxymethyl, 1,2,4-triazole-1H, 1-pyrazole-1H, 2-thiophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1, 2,4-oxadiazol-3-yl, benzoxazol-2-yl,
1 Ethylbenzimidazol-2-yl, Piperidin-1 -yl oder durch s Reste aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Trifluormethyl und Halogen substituiertes Phenyl, 1 ethylbenzimidazol-2-yl, piperidin-1-yl or phenyl substituted by s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,
R5 bedeutet Wassetrstoff, (Ci-C6)-Alkyl, (C3-C7)-Cycloalkyl, Halogen-(Ci-C6)-alkyl, (C3-C7)-Cycloalkylmethyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, R 5 means hydrogen, (Ci-C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halogen-(Ci-C 6 )-alkyl, (C3-C 7 )-cycloalkylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,
Acetylmethyl, Methoxymethyl, Methoxyethyl, Benzyl, Pyrazin-2-yl, Furan-2-yl, Acetylmethyl, Methoxymethyl, Methoxyethyl, Benzyl, Pyrazin-2-yl, Furan-2-yl,
Tetrahydrofuran-2-yl, Morpholin, Dimethylamino oder durch p Reste aus der Gruppe bestehend aus Methyl, Methoxy, Trifluormethyl und Halogen substituiertes Phenyl, Tetrahydrofuran-2-yl, morpholine, dimethylamino or phenyl substituted by p radicals from the group consisting of methyl, methoxy, trifluoromethyl and halogen,
W bedeutet O, CO oder CRc6Rc7, Rc1 bedeutet Hydroxy, W means O, CO or CR c6 R c7 , R c1 means hydroxy,
Rc2 und Rc5 bedeuten unabhängig voneinander jeweils Wasserstoff oder Methyl, oder Rc2 und Rc5 bilden gemeinsam eine Ethylen- oder Vinylengruppe, Rc3, Rc4, Rc6 und Rc7 bedeuten unabhängig voneinander jeweils Wasserstoff oder Methyl, R c2 and R c5 each independently represent hydrogen or methyl, or R c2 and R c5 together form an ethylene or vinylene group, R c3 , R c4 , R c6 and R c7 each independently represent hydrogen or methyl,
Rp1 bedeutet Wasserstoff, R p1 means hydrogen,
RP2 bedeutet (Ci-C4)-Alkyl, RP 2 means (Ci-C 4 )-alkyl,
Rp3 bedeutet Wasserstoff, (Ci-C )-Alkyl oder Cycloproyl, Rn1 bedeutet Cycloproyl, Rn2 bedeutet Wasserstoff, X1 bedeutet N oder CR2, R p3 means hydrogen, (Ci-C)-alkyl or cycloproyl, R n1 means cycloproyl, R n2 means hydrogen, X 1 means N or CR 2 ,
X2 bedeutet N oder CH, X 2 means N or CH,
mit der Maßgabe, dass mindestens einer der beiden Reste X1 und X2 N bedeutet, R2 bedeutet Wasserstoff, Halogen, (Ci-C )-Alkyl, with the proviso that at least one of the two radicals X 1 and X 2 means N, R 2 means hydrogen, halogen, (Ci-C)-alkyl,
Y bedeutet (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, OR6, S(O)nR7, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl- SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl-NR6SO2R7, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, wobei die beiden letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Y means (Ci-C 6 )-alkyl, halogen-(Ci-C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, OR 6 , S(O) n R 7 , (Ci-C 6 )- Alkyl-S(O) n R 7 , (Ci-C 6 )-Alkyl-OR 6 , (Ci-C 6 )-Alkyl-CON(R 6 ) 2 , (Ci-C 6 )-Alkyl-SO 2 N (R 6 ) 2 , (Ci-C 6 )-alkyl-NR 6 COR 6 , (Ci-C 6 )-alkyl-NR 6 SO 2 R 7 , (Ci-C 6 )-alkyl-heteroaryl, (Ci- C6)-alkyl-heterocyclyl, where the last two radicals are each replaced by s radicals from the group consisting of halogen, (Ci-C6)-alkyl, halogen-(Ci-C6)-alkyl, S(O) n -(Ci- C6)-alkyl, (Ci-Ce)-alkoxy and halogen-(Ci-C6)-alkoxy are substituted, and where heterocyclyl carries n oxo groups,
Z bedeutet Wasserstoff, Halogen, Cyano, Rhodano, Nitro, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2- C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (Cs-CeJ-CycloalkyKCi-Ce)- alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR6, COOR6, OCOOR6, NR6COOR6, C(O)N(R6)2, NR6C(O)N(R6)2, OC(O)N(R6)2, C(O)NR6OR6, OSO2R7, S(O)nR7, SO2OR6, SO2N(R6)2, NR6SO2R7, NR6COR6, (Ci-C6)-Alkyl-S(O)nR7, (Ci-C6)-Alkyl-OR6, (Ci-C6)- Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R7, (Ci-C6)-Alkyl-CO2R6, (Ci-C6)-Alkyl-SO2OR6, (Ci- C6)-Alkyl-CON(R6)2, (Ci-C6)-Alkyl-SO2N(R6)2, (Ci-C6)-Alkyl-NR6COR6, (Ci-C6)-Alkyl- NR1SO2R7, N(R6)2, P(O)(OR10)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die 3 letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-C6)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei Z means hydrogen, halogen, cyano, rhodano, nitro, (Ci-C6)-alkyl, halogen-(Ci-C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halogen-(C 2 -C 6 ) -alkenyl, (C 2 -C 6 )-alkynyl, halogen-(C 2 - C 6 )-alkynyl, (C3-C 6 )-cycloalkyl, halogen-(C3-C 6 )-cycloalkyl, (Cs-CeJ- CycloalkyKCi-Ce)-alkyl, halogen-(C3-C 6 )-cycloalkyl-(Ci-C 6 )-alkyl, COR 6 , COOR 6 , OCOOR 6 , NR 6 COOR 6 , C(O)N(R 6 ) 2 , NR 6 C(O)N(R 6 ) 2 , OC(O)N(R 6 ) 2 , C(O)NR 6 OR 6 , OSO 2 R 7 , S(O) n R 7 , SO 2 OR 6 , SO 2 N(R 6 ) 2 , NR 6 SO 2 R 7 , NR 6 COR 6 , (Ci-C 6 )-alkyl-S(O) n R 7 , (Ci-C 6 )-alkyl- OR 6 , (Ci-C 6 )- Alkyl-OCOR 1 , (Ci-C 6 )-Alkyl-OSO 2 R 7 , (Ci-C 6 )-Alkyl-CO 2 R 6 , (Ci-C6)-Alkyl-SO 2 OR 6 , (Ci-C 6 )-Alkyl-CON(R 6 ) 2 , (Ci-C 6 )-Alkyl-SO 2 N(R 6 ) 2 , (Ci-C 6 )-Alkyl-NR 6 COR 6 , (Ci-C 6 ) -Alkyl- NR 1 SO 2 R 7 , N(R 6 ) 2 , P(O)(OR 10 ) 2 , heteroaryl, heterocyclyl or phenyl, where the last 3 radicals are each replaced by s radicals from the group consisting of halogen, nitro , cyano, (Ci-C 6 )-alkyl, halogen-(Ci-C 6 )-alkyl, (C3-C 6 )-cycloalkyl, S(O) n -(Ci-C 6 )-alkyl, (Ci- C6)-alkoxy and halogen-(Ci-C6)-alkoxy are substituted, and where
Heterocyclyl n Oxogruppen trägt, Heterocyclyl n carries oxo groups,
Z und R2 bilden gemeinsam mit den beiden Kohlenstoffatomen, an denen sie gebunden sind, einen fünf- oder sechsgliedrigen Ring bestehend aus t Z and R 2 together with the two carbon atoms to which they are bonded form a five- or six-membered ring consisting of t
Kohlenstoffatomen und p Heteroatomen aus der Gruppe bestehend aus N, O und S, wobei dieser Ring durch q Reste aus der Gruppe bestehend aus Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C )-alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy- methyl, (Ci-Ce)-Alkoxy und Halogen-(Ci-C6)-alkoxy substituiert ist, Carbon atoms and p heteroatoms from the group consisting of N, O and S, this ring being replaced by q radicals from the group consisting of halogen, nitro, cyano, (Ci-C 6 )-alkyl, halogen-(Ci-C )-alkyl , S(O) n -(Ci- C6 )-alkyl, (Ci-Ce)-alkoxy-methyl, (Ci-Ce)-alkoxy and halogen-(Ci-C6)-alkoxy is substituted,
R6 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C2- C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkenyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-Ce)-Alkyl- Heteroaryl, Heterocycl, (Ci-C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)- Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR8-Heteroaryl, (Ci-C6)-Alkyl-NR8-Heterocyclyl wobei die 21 letztgenannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C4)-Alkoxy-(C2-C6)- alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R 6 means hydrogen, (Ci-C 6 )-alkyl, (Ci-C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 ) -Alkynyl, (C 2 -C 6 )-haloalkynyl, (C3-C 6 )-cycloalkyl, (C 3 - C 6 )-cycloalkenyl, (C3-C 6 )-halocycloalkyl, (Ci-C6)-alkyl-O -(Ci-C 6 )-alkyl, (C 3 -C 6 )- cycloalkyl-(Ci-C 6 )-alkyl, phenyl, phenyl-(Ci-C 6 )-alkyl, heteroaryl, (Ci-Ce)- Alkyl-Heteroaryl, Heterocycl, (Ci-C 6 )-Alkyl-Heterocyclyl, (Ci-C 6 )-Alkyl-O-Heteroaryl, (Ci-C 6 )-Alkyl-O-Heterocyclyl, (Ci-C 6 )- Alkyl-NR 8 -Heteroaryl, (Ci-C 6 )-Alkyl-NR 8 -Heterocyclyl, where the last 21 residues are each replaced by s residues from the group consisting of cyano, halogen, nitro, rhodano, OR 8 , S(O) n R 9 , N(R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO2R 9 , CO 2 R 8 , COSR 9 , CON(R 8 ) 2 and ( Ci-C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl are substituted, and where heterocyclyl carries n oxo groups,
R7 bedeutet (Ci -C6)-Al kyl , (C2-C6)-Al kenyl , (C2-C6)-Al kinyl , (C3-C6)-Cycloal kyl , (C3- C6)-Cycloalkenyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (Ci- C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)-Alkyl-O-Heterocyclyl, (Ci- C6)-Alkyl-NR3-Heteroaryl, (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei diese 17 Reste jeweils durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR8, S(O)nR9, N(R8)2, NR8OR8, COR8, OCOR8, SCOR9, NR8COR8, NR8SO2R9, CO2R8, COSR9, CON(R8)2 und (Ci-C )-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R 7 means (Ci -C 6 )-alkyl, (C 2 -C 6 )-al kenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 - C 6 )-cycloalkenyl, (Ci-C6)-alkyl-O-(Ci-C 6 )-alkyl, (C3-C6)-cycloalkyl-(Ci-C 6 )-alkyl, phenyl, phenyl-(Ci-C6 )-alkyl, heteroaryl, (Ci-C6)-alkyl-heteroaryl, heterocyclyl, (Ci-C 6 )-alkyl-heterocyclyl, (Ci-C 6 )-alkyl-O-heteroaryl, (Ci-C 6 )-alkyl -O-heterocyclyl, (Ci-C6)-alkyl-NR 3 -heteroaryl, (Ci-C6)-alkyl-NR 3 -heterocyclyl, where these 17 residues are each replaced by s residues from the group consisting of cyano, halogen, nitro, Rhodano, OR 8 , S(O) n R 9 , N(R 8 ) 2 , NR 8 OR 8 , COR 8 , OCOR 8 , SCOR 9 , NR 8 COR 8 , NR 8 SO 2 R 9 , CO 2 R 8 , COSR 9 , CON(R 8 ) 2 and (Ci-C )-alkoxy-(C2-C 6 )-alkoxycarbonyl are substituted, and where heterocyclyl n carries oxo groups,
R8 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder Phenyl, R 8 means hydrogen, (Ci-C 6 )-alkyl, (C2-C 6 )-alkenyl, (C2-C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C3-C6)-cycloalkyl- (Ci-C 6 )alkyl or phenyl,
R9 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl oder Phenyl, R 9 means (Ci-C 6 )-alkyl, (C2-C 6 )-alkenyl, (C 2 -C 6 )-alkynyl or phenyl,
R10 bedeutet (Ci-C4)-Alkyl, n bedeutet 0, 1 oder 2, p bedeutet 0, 1 , 2 oder 3, q bedeutet 0, 1 , 2, 3 oder 4, s bedeutet 0, 1 , 2, 3, 4 oder 5, t bedeutet e 1 , 2, R 10 means (Ci-C 4 )-alkyl, n means 0, 1 or 2, p means 0, 1, 2 or 3, q means 0, 1, 2, 3 or 4, s means 0, 1, 2, 3, 4 or 5, t means e 1 , 2,
3, 4, 5 oder 6. 3, 4, 5 or 6.
4. Herbizide Mittel, gekennzeichnet durch einen herbizid wirksamen Gehalt an mindestens einer Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 3. 4. Herbicidal agents, characterized by a herbicidally active content of at least one compound of the formula (I) according to one of claims 1 to 3.
5. Herbizide Mittel nach Anspruch 4 in Mischung mit Formulierungshilfsmitteln. 5. Herbicidal agents according to claim 4 in a mixture with formulation aids.
6. Herbizide Mittel nach Anspruch 4 oder 5 enthaltend mindestens einen weiteren Pestizid wirksamen Stoff aus der Gruppe Insektizide, Akarizide, Herbizide, Fungizide, Safener und Wachstumsregulatoren. 6. Herbicidal agent according to claim 4 or 5 containing at least one further pesticide-active substance from the group of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.
7. Herbizide Mittel nach Anspruch 6 enthaltend einen Safener. 7. Herbicidal composition according to claim 6 containing a safener.
8. Herbizide Mittel nach Anspruch 7 enthaltend cyprosulfamid, cloquintocet-mexyl, mefenpyr-diethyl oder isoxadifen-ethyl. 8. Herbicidal composition according to claim 7 containing cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.
9. Herbizide Mittel nach einem der Ansprüche 4 bis 8 enthaltend ein weiteres Herbizid. 9. Herbicidal composition according to one of claims 4 to 8 containing a further herbicide.
10. Verfahren zur Bekämpfung unerwünschter Pflanzen, dadurch gekennzeichnet, daß man eine wirksame Menge mindestens einer Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 3 oder eines herbiziden Mittels nach einem der Ansprüche 4 bis 8 auf die Pflanzen oder auf den Ort des unerwünschten Pflanzenwachstums appliziert. 10. A method for combating undesirable plants, characterized in that an effective amount of at least one compound of the formula (I) according to one of claims 1 to 3 or a herbicidal agent according to one of claims 4 to 8 is applied to the plants or to the location of the applied to unwanted plant growth.
1 1 . Verwendung von Verbindungen der Formel (I) gemäß einem der Ansprüche 1 bis 3 oder von herbiziden Mitteln nach einem der Ansprüche 4 bis 8 zur Bekämpfung unerwünschter Pflanzen. 1 1 . Use of compounds of the formula (I) according to one of claims 1 to 3 or of herbicidal agents according to one of claims 4 to 8 for combating undesirable plants.
12. Verwendung nach Anspruch 1 1 , dadurch gekennzeichnet, daß die 12. Use according to claim 1 1, characterized in that the
Verbindungen der Formel (I) zur Bekämpfung unerwünschter Pflanzen in Kulturen von Nutzpflanzen eingesetzt werden. Compounds of the formula (I) are used to combat undesirable plants in crops of useful plants.
13. Verwendung nach Anspruch 12, dadurch gekennzeichnet, daß die Nutzpflanzen transgene Nutzpflanzen sind. 13. Use according to claim 12, characterized in that the crop plants are transgenic crop plants.
PCT/EP2014/064897 2013-07-16 2014-07-11 6-azinone-2-carbonyl derivatives and their use as herbicides WO2015007633A1 (en)

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WO2017042259A1 (en) 2015-09-11 2017-03-16 Bayer Cropscience Aktiengesellschaft Hppd variants and methods of use
US11180770B2 (en) 2017-03-07 2021-11-23 BASF Agricultural Solutions Seed US LLC HPPD variants and methods of use

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WO2012039141A1 (en) * 2010-09-24 2012-03-29 クミアイ化学工業株式会社 6-acylpyridin-2-one derivative and herbicide
WO2012123416A1 (en) * 2011-03-15 2012-09-20 Bayer Cropscience Ag N-(1,2,5-oxadiazol-3-yl)pyridinecarboxamides and use thereof as herbicides

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WO2012039141A1 (en) * 2010-09-24 2012-03-29 クミアイ化学工業株式会社 6-acylpyridin-2-one derivative and herbicide
WO2012123416A1 (en) * 2011-03-15 2012-09-20 Bayer Cropscience Ag N-(1,2,5-oxadiazol-3-yl)pyridinecarboxamides and use thereof as herbicides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017042259A1 (en) 2015-09-11 2017-03-16 Bayer Cropscience Aktiengesellschaft Hppd variants and methods of use
US11180770B2 (en) 2017-03-07 2021-11-23 BASF Agricultural Solutions Seed US LLC HPPD variants and methods of use

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