WO2015007633A1 - Dérivés de 6-azinon-2-carbonyle et leur utilisation comme herbicides - Google Patents

Dérivés de 6-azinon-2-carbonyle et leur utilisation comme 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)
English (en)
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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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    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des dérivés de 6-azinon-2-carbonyle de la formule générale (I) utilisés comme herbicides. Dans cette formule (I), Y et Z représentent des radicaux comme hydrogène, des radicaux organiques comme alkyle, et d'autres radicaux comme halogène. X1 et X2 représentent azote et carbone, Q représente un radical azolylcarbamoyle.
PCT/EP2014/064897 2013-07-16 2014-07-11 Dérivés de 6-azinon-2-carbonyle et leur utilisation comme herbicides WO2015007633A1 (fr)

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Cited By (2)

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

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012039141A1 (fr) * 2010-09-24 2012-03-29 クミアイ化学工業株式会社 Dérivé de l'6-acylpyridin-2-one et herbicide
WO2012123416A1 (fr) * 2011-03-15 2012-09-20 Bayer Cropscience Ag N-(1,2,5-oxadiazol-3-yl)pyridinecarboxamides et leur utilisation comme herbicides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012039141A1 (fr) * 2010-09-24 2012-03-29 クミアイ化学工業株式会社 Dérivé de l'6-acylpyridin-2-one et herbicide
WO2012123416A1 (fr) * 2011-03-15 2012-09-20 Bayer Cropscience Ag N-(1,2,5-oxadiazol-3-yl)pyridinecarboxamides et leur utilisation comme herbicides

Cited By (2)

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

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