DK2785181T3 - 2-(substitueret phenyl)-cyclopentan-1,3-dionforbindelser og derivater deraf - Google Patents

2-(substitueret phenyl)-cyclopentan-1,3-dionforbindelser og derivater deraf Download PDF

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DK2785181T3
DK2785181T3 DK12797857.5T DK12797857T DK2785181T3 DK 2785181 T3 DK2785181 T3 DK 2785181T3 DK 12797857 T DK12797857 T DK 12797857T DK 2785181 T3 DK2785181 T3 DK 2785181T3
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alkyl
formula
compound
independently
fluoroalkyl
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Alaric James Avery
Mangala Mahadev Phadte
James Nicholas Scutt
John Benjamin Taylor
Russell Colin Viner
Jeffrey Steven Wailes
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Syngenta Ltd
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Claims (15)

1. Forbindelse med formel (I):
(I). hvor: X er methyl eller chlor; R1 er methyl eller chlor; R2 er hydrogen, methyl, ethyl, n-propyl, cyclopropyl, vinyl, ethynyl, fluor, chlor, brom, methoxy, ethoxy eller fluormethoxy; R3, R4 og R5 uafhængigt af hinanden er hydrogen, Ci-C5alkyl, C2-C^alkenyl, C2-C4alkynyl, Ci-C2fluoralkyl eller Ci-C3alkoxyCi-C3alkyl; og R6 er hydrogen; Ci-C5alkyl; C2-C4alkenyl; C2-C4alkynyl; R6aa-C=C-CH2-; Ci-C2f luoralkyl; Ci-C3alkoxyCi-C3alkyl; Ci-C3alkylthioCi-C3alkyl; Ci-C3alkylsulf inylCi-C3alkyl; Ci-C3alkylsulf onylCi-C3alkyl; C3-C4cycloalkyl; eller en usubstitueret 4, 5 eller 6- leddet monocyklisk heterocyclyl med ét ringheteroatom, der er udvalgt uafhængigt blandt oxygen, svovl og nitrogen og bundet i et ringcarbonatom i heterocyclyl'en; eller R6 er Q-(CH2) m_CH (R7)-, hvor m er 0 eller 1, og enten R7 er hydrogen, eller R7 og R5 sammen er en binding, og Q er en eventuelt substitueret heterocyclyl som defineret nedenfor; eller R6 er Het-CH(R8)-, hvor enten R8 er hydrogen, eller R8 og R5 sammen er en binding, og Het er en eventuelt substitueret heteroaryl som defineret nedenfor; eller R6 er C3-C6cycloalkylCi-C2alkyl-; eller er C4-C6cycloalkylCi-C2alkyl-, der er substitueret i et cycloalkylringcarbonatom, som ikke er ringcarbonatomet, der er koblet til -Ci-C2alkyldelen, og som ikke er bundet direkte til ringcarbonatomet, der er koblet til -Ci-C2alkyldelen, med en eller to ringsubstituenter, der uafhængigt er: =N-0-R10, oxo (=0) , Ci-C4alkoxy, Ci-C2haloalkoxy, 2- (Ci-C3alkoxy) -ethoxy, C3- C5cycloalkyloxy, (C3-C5cycloalkyl)methoxy, C2-C3alkenyl-CH2-oxy, Ci-C3alkyl eller Ci-C2fluoralkyl; eller benzyloxy, hvori phenylringen eventuelt er substitueret med en eller to substituenter, der uafhængigt er methyl, methoxy, Cifluoralkoxy, fluor eller chlor; eller R6 er benzyl, der eventuelt er substitueret på dens phenylring med en eller to substituenter, der uafhængigt er: cyano, -C=c-R6A, -C (R6B) =C (R6C) (R6CC) , -C (0)-R6D, -S(0)2-R6E, - N (R6f) (R6g) , Ci-C3alkoxy, Ci-C2f luoralkoxy, cyclopropyloxy, CH2=CH-CH2-0-, HC=C-CH2-0-, halogen, Ci-C2alkyl eller Cifluoralkyl; eller R3 og R4 sammen er -(CH2)ni- eller - (CH2) n2-X4- (CH2) n3-, og R5 og R6 er som defineret heri, eller R5 og R6 sammen er -(CH2) ni — eller - (CH2) ^-X1- (CH2) n3-, og R3 og R4 er som defineret heri ; eller R4 og Rs sammen er -C (R11) (R12)-C (R13) (R14)-C (R15) (R16) -C (R17) (R18)-, -C (R11) (R12)-C (R13) =C (R15)-C (R17) (R18) - eller CH (R19) -C (R20) (R21) -CH (R22) -; hvor Q er en 4 til 7-leddet monocyklisk eller en 8 til 11-leddet fusioneret bicyklisk heterocyclyl med en eller to ringheteroatomer, der er udvalgt uafhængigt blandt oxygen, svovl og nitrogen; og hvor heterocyclyl'en Q eventuelt er substitueret med 1 eller 2 ringcarbonsubstituenter, der uafhængigt er Ci-C3alkyl, Ci-C2fluoralkyl eller oxo (=0) , og/eller eventuelt er substitueret med én Ci-C4alkyl, Ci-C2fluoralkyl, Ci-C4alkoxy, Ci-C2fluoralkoxy, R9-C(0)- eller Ci~ C2alkyl-S (0) 2-substituent på et ringnitrogen, hvis det er til stede, og/eller eventuelt er substitueret med en eller to oxo (=0)-substituenter på et ringsvovl, hvis det er til stede; hvor Het er en heteroaryl, der er bundet i et ringcarbon, der eventuelt er substitueret med 1, 2 eller 3 ringcarbonsubstituenter, der uafhængigt er Ci-C3alkyl, Ci~ C2fluoralkyl, Ci-C3alkyl-C(0)-, Ci-C2fluoralkyl-C(0)-, -C(0)-N (R6h) (R6j) , -S(0)2-R6E, -N (RoF) (R6g) , hydroxy (herunder en hvilken som helst oxotautomer) , C2-C3alkenyl, C(R6BB)=C(R6cl) (R6c2) , C2-C3alkynyl, -C^c-R6AA, C!-C3alkoxy, C^ C2f luoralkoxy, cyclopropyloxy, CH2=CH-CH2-0-, HC=C-CH2-0-, halogen, cyano eller nitro; forudsat at et hvilket som helst ikke-fluor-halogen, alkoxy, fluoralkoxy, cyclopropyloxy, CH2=CH-CH2-0- eller HC=C-CH2-0- ikke er substitueret i et hvilket som helst ringcarbon, der er bundet direkte til et ringnitrogen i heteroaryl'en; og/eller i tilfælde af en 5-leddet heteroarylring, der indeholder et ringnitrogenatom, der ikke er del af en C=N-ringdobbeltbinding, heteroaryl'en eventuelt er substitueret på ringnitrogenatomet, der ikke er del af en C=N- ringdobbeltbinding, med én Ci-C3alkyl, Ci-C2f luoralkyl, Ci~ C3alkyl-C(0)Ci-C2fluoralkyl-C(0)- eller Ci-C2alkyl-S(0) 2-substituent; hvor: R6a er hydrogen, methyl, Cifluoralkyl, fluor, chlor eller brom; R6aa er Cif luoralkyl, fluor, chlor eller brom; r6b, r6c Qg r6cc u a f hæng i g t er hydrogen, methyl, Cif luoralkyl, fluor eller chlor; forudsat at R6B, R6C og Rscc i alt ikke indeholder mere end ét carbonatom, og R6B, Rsc og Rscc i alt ikke omfatter mere end ét chlor; og R6bb, r6c1 og R6c2 uafhængigt er hydrogen, methyl, Cif luoralkyl, fluor eller chlor; forudsat at R6BB, R6C1 og R6C2 i alt ikke indeholder mere end ét carbonatom, og R6BB, R6C1 og Rsc2 i alt ikke omfatter mere end ét chlor; og forudsat at C (R6bb) =C (R6c1) (R6c2) ikke er C2-C3alkenyl; og R6d og R6e uafhængigt er Ci-C3alkyl, Cifluoralkyl eller N (R6h) (R6j) ; R6f er -C (0)-Ci-C2alkyl, -C (0)-Cifluoralkyl, -S (0) 2-Ci-C2alkyl, -S (0) 2-Cifluoralkyl, Ci-C2alkyl eller Cifluoralkyl; R6g og R6j uafhængigt er hydrogen, methyl eller Cifluoralkyl; og R6h er hydrogen, Ci-C2alkyl (f.eks. methyl) eller Cifluoralkyl; and hvor R9 er Ci-C4alkyl, C2-C4alkenyl, der er bundet i et carbonatom, der er del af C=C-dobbeltbindingen, Ci~ C2fluoralkyl, Ci-C2alkoxymethyl-, Ci-C3alkoxy, cyclopropyl, furanyl, morpholin-4-yl, isoxazol-3-yl, 5-methyl-isoxazol-3-yl, pyrazol-5-yl, 3-methylpyrazol-5-yl, l-methylpyrazol-5-yl, 1,3-dimethylpyrazol-5-yl; eller phenyl eller phenyl, der er substitueret med 1 eller 2 substituenter, der uafhængigt er methyl, ethyl, Cifluoralkyl, methoxy, Cifluoralkoxy, fluor eller chlor; hvor R10 og R23 uafhængigt er hydrogen, Ci-C4alkyl, Ci-C2fluoralkyl, 2-(Ci-C3alkoxy)-ethyl, C3-C5cycloalkyl eller (C3-Cscycloalkyl)methyl; hvor X1 er 0, S, S (0) , S(0)2, NH, N (Ci-C3alkyl) , N (Ci-C3alkoxy) , C(H) (Ci-C2alkyl) , C(Ci-C2alkyl)2, C (H) (Ci-C3alkoxy) eller C (Me) (Ci-C2alkoxy) ; og ni er 2, 3, 4 eller 5; og n2 og n3 uafhængigt er 1, 2 eller 3, forudsat at n2 + n3 er 2, 3 eller 4; hvor: R11 og R18 begge er hydrogen, eller R11 og R18 er sammen og danner en -0- eller -Ci-C2alkylenbro; og R12 og R17 uafhængigt er hydrogen, Ci-C3alkyl eller C2-C2alkoxyCi-C2alkyl; R , R og R uafhængigt er hydrogen, Ci~C3alkyl eller C2-C2alkoxyCi-C2alkyl, forudsat at 1, 2 eller alle af R13, R14 og R15 er hydrogen; og R16 er hydrogen; Ci-C3alkyl; Ci-C2alkoxyCi-C2alkyl; phenyl, der eventuelt er substitueret med 1, 2 eller 3 af uafhængigt methyl, Cifluoralkyl, methoxy, Cifluoralkoxy, methylthio, fluor, chlor, cyano eller nitro; eller pyridinyl, der er bundet i et ringcarbon og eventuelt er substitueret med 1, 2 eller 3 ringcarbonsubstituenter, der uafhængigt er methyl, Cifluoralkyl, methoxy, Cifluoralkoxy, hydroxy (herunder en hvilken som helst oxotautomer), fluor, chlor, cyano eller nitro, forudsat at et eventuelt chlor, methoxy eller Cifluoralkoxy ikke er substitueret i noget ringcarbon, der er bundet direkte til ringnitrogenet i pyridinyl'en; og hvor: R19 og R22 uafhængigt er hydrogen, Ci-C3alkyl eller C2-C2alkoxyCi-C2alkyl; og R20 og R21 uafhængigt er hydrogen, Ci~C3alkyl eller C2-C2alkoxyCi-C2alkyl ; eller R20 og R21 sammen er oxo (=0) , =N-0-R23 eller =CH2; eller R20 og R21 sammen med carbonatomet, hvortil de er bundet, danner en 5, 6 eller 7-leddet mættet heterocyclyl, hvilken heterocyclyl har to ringheteroatomer, der uafhængigt er oxygen eller svovl, og som ikke er direkte bundet til hinanden, og hvor heterocyclyl' en eventuelt er substitueret med 1, 2 eller 3 ringcarbonsubstituenter, der uafhængigt er Ci-C2alkyl; og hvor: G er hydrogen; et landbrugsmæssigt acceptabelt metal eller en landbrugsmæssigt acceptabel sulfonium- eller ammoniumgruppe; eller G er Ci-Csalkyl, C2-C8fluoralkyl, phenylCi-C8alkyl (hvor phenyl eventuelt er substitueret med 1, 2 eller 3 af uafhængigt Ci- Csalkyl, Ci-C3f luoralkyl, Ci-C3alkoxy, Ci-C3f luoralkoxy, Ci~ Csalkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano eller nitro) , heteroarylCi-C8alkyl (hvor heteroaryl eventuelt er substitueret med 1, 2 eller 3 af uafhængigt C7- C3alkyl, Ci-C3f luoralkyl, Ci-C3alkoxy, Ci-C3f luoralkoxy, C7- C3alkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano eller nitro), C2-C7alkenyl-CH2-, C2-C7alkenyl-CH (Me)-, C2-C7alkenyl-CMe2-, C2-C4f luoralkenyl-CH2-, C2-C7alkynyl-CH2-, C (Xa) -Ra, -C (Xb) -Xc-Rb, -C (Xd)-N (Rc)-Rd, -S02-Re, -P (Xe) (Rf) -Rg eller -CH2-Xf-Rh; hvor Xa, Xb, Xc, Xd, Xe og Xf uafhængigt af hinanden er oxygen eller svovl; og hvor Ra er H, Ci-C2ialkyl, C2-C2ialkenyl, C2-Ci8alkynyl, Ci-Ciof luoralkyl, Ci-Ciocyanoalkyl, Ci-Cionitroalkyl, C4- Cioaminoalkyl, Ci-Csalkylamino (C1-C5) alkyl, C2-C8dialkylamino (C4-C5) alkyl, C3-C7cycloalkyl (C1-C5) alkyl, Ci-C5alkoxy (C1-C5) alkyl, C3-C5alkenyloxy (C1-C5) alkyl, C3-C5alkynyloxy (C1-C5) alkyl, C4-Csalkylthio (C1-C5) alkyl, Ci-Csalkylsulfinyl (C1-C5) alkyl, C4- Csalkylsulf onyl (C1-C5) alkyl, C2-C8alkylidenaminoxy (C1-C5) alkyl, Ci-Csalkylcarbonyl (C1-C5) alkyl, Ci-Csalkoxycarbonyl (C1-C5) alkyl, aminocarbonyl (C1-C5) alkyl, Ci-Csalkylaminocarbonyl (C1-C5) alkyl, C2-C8dialkylaminocarbonyl (C1-C5) alkyl, C4- Csalkylcarbonylamino (C1-C5) alkyl, N- (C1-C5) alkylcarbonyl-N- (Ci — C5) alkylamino (C1-C5) alkyl, C3-C6trialkylsilyl (C1-C5) alkyl, phenyl(C1-C5)alkyl (hvor phenyl eventuelt er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3f luoralkyl, Ci~ C3alkoxy, Ci-C3fluoralkoxy, Ci-C3alkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano eller nitro), heteroaryl(Ci— C5) alkyl (hvor heteroaryl eventuelt er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3fluoralkyl, Ci-C3alkoxy, Ci-C3fluoralkoxy, Ci-C3alkylthio, Ci-C3alkylsulfinyl, Ci- Csalkylsulfonyl, halogen, cyano eller nitro), C2- Csfluoralkenyl, Cs-Cscycloalkyl; phenyl eller phenyl, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci- C3fluoralkyl, Ci-C3alkoxy, Ci-C3fluoralkoxy, halogen, cyano eller nitro; eller heteroaryl eller heteroaryl, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci- C3fluoralkyl, Ci-C3alkoxy, Ci-C3fluoralkoxy, halogen, cyano eller nitro; Rb er Ci-Cisalkyl, C3-Ci8alkenyl, C3-Ci8alkynyl, C2-Ciofluoralkyl, Ci-Ciocyanoalkyl, Ci-Cionitroalkyl, C2-Cioaminoalkyl, Ci- Csalkylamino (C1-C5) alkyl, C2-C8dialkylamino (C1-C5) alkyl, C3- Cvcycloalkyl (C1-C5) alkyl, Ci-C5alkoxy (C1-C5) alkyl, C3- Csalkenyloxy (C1-C5) alkyl, C3-Csalkynyloxy (C1-C5) alkyl, Ci- Csalkylthio (C1-C5) alkyl, Ci-Csalkylsulf inyl (C1-C5) alkyl, Ci- Csalkylsulfonyl (C1-C5) alkyl, C2-C8alkylidenaminoxy (C1-C5) alkyl, Ci-Csalkylcarbonyl (C1-C5) alkyl, Ci-C5alkoxycarbonyl (C1-C5) alkyl, aminocarbonyl (C1-C5) alkyl, Ci-Csalkylaminocarbonyl (C1-C5) alkyl, C2-C8dialkylaminocarbonyl (C1-C5) alkyl, Ci- Csalkylcarbonylamino (C1-C5) alkyl, N- (C1-C5) alkylcarbonyl-N- (Ci~ C5) alkylamino (C1-C5) alkyl, C3-C6trialkylsilyl (C1-C5) alkyl, phenyl(C1-C5)alkyl (hvor phenyl eventuelt er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3f luoralkyl, Ci- Csalkoxy, Ci-C3fluoralkoxy, Ci-C3alkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano eller nitro), heteroarylCi-Csalkyl (hvor heteroaryl eventuelt er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3fluoralkyl, Ci-C3alkoxy, Ci~C3fluoralkoxy, Ci-C3alkylthio, Ci-C3alkylsulfinyl, Ci~ Csalkylsulfonyl, halogen, cyano eller nitro) , C3- Csfluoralkenyl, Cs-Cscycloalkyl; phenyl eller phenyl, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci~ C3fluoralkyl, Ci-C3alkoxy, Ci~C3fluoralkoxy, halogen, cyano eller nitro; eller heteroaryl eller heteroaryl, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci~ C3fluoralkyl, Ci-C3alkoxy, Ci-C3fluoralkoxy, halogen, cyano eller nitro; og Rc og Rd hver uafhængigt af hinanden er hydrogen, Ci-Ci0alkyl, C3-Ci0alkenyl, C3-Ci0alkynyl, C2_Ciof luoralkyl, Ci-Ciocyanoalkyl, Ci-Cionitroalkyl, Ci-Cioaminoalkyl, Ci-Csalkylamino (C1-C5) alkyl, C2-C8dialkylamino (C1-C5) alkyl, C3-C7cycloalkyl (C1-C5) alkyl, C7- C5alkoxy (C1-C5) alkyl, C3-C5alkenyloxy (C1-C5) alkyl, C3- Csalkynyloxy (C1-C5) alkyl, Ci-Csalkylthio (C1-C5) alkyl, Ci- Csalkylsulfinyl (C1-C5) alkyl, Ci-Csalkylsulfonyl (C1-C5) alkyl, C2-Csalkylidenaminoxy (C1-C5) alkyl, Ci-Csalkylcarbonyl (C1-C5) alkyl, Ci-Csalkoxycarbonyl (C1-C5) alkyl, aminocarbonyl (C1-C5) alkyl, Ci-Csalkylaminocarbonyl (C1-C5) alkyl, C2-C8dialkylaminocarbonyl (Ci-C5) alkyl, Ci-Csalkylcarbonylamino (C1-C5) alkyl, N- (Ci~ C5) alkylcarbonyl-Λί- (C2-C5) alkylaminoalkyl, C3- Cetrialkylsilyl (C1-C5) alkyl, phenyl (C1-C5) alkyl (hvor phenyl eventuelt er substitueret med 1, 2 eller 3 af uafhængigt Ci- C3alkyl, Ci-C3fluoralkyl, Ci-C3alkoxy, Ci-C3fluoralkoxy, Ci~ C3alkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano eller nitro), heteroaryl(C1-C5)alkyl (hvor heteroaryl eventuelt er substitueret med 1, 2 eller 3 af uafhængigt Ci- Csalkyl, Ci-C3fluoralkyl, Ci-C3alkoxy, Ci-C3fluoralkoxy, Ci~ C3alkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano eller nitro), C2-Csfluoralkenyl, C3-C8cycloalkyl; phenyl eller phenyl, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3fluoralkyl, Ci-C3alkoxy, Ci~ C3fluoralkoxy, halogen, cyano eller nitro; heteroaryl eller heteroaryl, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3fluoralkyl, Ci-C3alkoxy, Ci-C3fluoralkoxy, halogen, cyano eller nitro; heteroarylamino eller heteroarylamino, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3fluoralkyl, Ci-C3alkoxy, Ci- C3fluoralkoxy, halogen, cyano eller nitro; diheteroarylamino eller diheteroarylamino, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3f luoralkyl, Ci-C3alkoxy, C7-C3fluoralkoxy, halogen, cyano eller nitro; phenylamino eller phenylamino, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci~C3f luoralkyl, Ci-C3alkoxy, Ci- C3fluoralkoxy, halogen, cyano eller nitro; diphenylamino eller diphenylamino, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3f luoralkyl, Ci-C3alkoxy, Ci- C3fluoralkoxy, halogen, cyano eller nitro; eller C3-C7cycloalkylamino, di (C3-C7cycloalkyl) amino eller C3- C7cycloalkoxy ; eller Rc og Rd sammen med nitrogenatomet, hvortil de er bundet, danner en usubstitueret 4, 5, 6 eller 7-leddet ring, der eventuelt indeholder ét heteroatom, der er udvalgt blandt 0 eller S; og Re er Ci-Cioalkyl, C2-Ci0alkenyl, C2-Ci0alkynyl, Ci-Ci0fluoralkyl, Ci-Ciocyanoalkyl, Ci-Cionitroalkyl, Ci-Ci0aminoalkyl, Cg-Csalkylamino (C1-C5) alkyl, C2-C8dialkylamino (C1-C5) alkyl, C3- C7cycloalkyl (C1-C5) alkyl, Cg-Csalkoxy (C1-C5) alkyl, C3- Csalkenyloxy (C1-C5) alkyl, Cg-Csalkynyloxy (C1-C5) alkyl, Cg- Csalkylthio (C1-C5) alkyl, Cg-Csalkylsulfinyl (C1-C5) alkyl, Cg-C5alkylsulfonyl (C1-C5) alkyl, C2-C8alkylidenaminoxy (C1-C5) alkyl, Ci-C5alkylcarbonyl (C1-C5) alkyl, Ci-C5alkoxycarbonyl (C1-C5) alkyl, aminocarbonyl (C1-C5) alkyl, Ci-C5alkylaminocarbonyl (C1-C5) alkyl, Cg-Csdialkylaminocarbonyl (C1-C5) alkyl, Cg- Csalkylcarbonylamino (C1-C5) alkyl, N- (C1-C5) alkylcarbonyl-I\7- (Cg-C5) alkylamino (C1-C5) alkyl, C3-C6trialkylsilyl (C1-C5) alkyl, phenyl(C1-C5)alkyl (hvor phenyl eventuelt er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3f luoralkyl, Cg- C3alkoxy, Ci-C3fluoralkoxy, Cg-C3alkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano eller nitro), heteroaryl (Cg-C5)alkyl (hvor heteroaryl eventuelt er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3fluoralkyl, Ci-C3alkoxy, Cg-C3fluoralkoxy, Ci-C3alkylthio, Ci-C3alkylsulfinyl, Cg- C3alkylsulfonyl, halogen, cyano eller nitro), C2- Csfluoralkenyl, C3-C8cycloalkyl; phenyl eller phenyl, der er substitueret med 1, 2 eller 3 af uafhængigt Cg-C3alkyl, cg- C3fluoralkyl, Ci-C3alkoxy, Ci-C3fluoralkoxy, halogen, cyano eller nitro; heteroaryl eller heteroaryl, der er substitueret med 1, 2 eller 3 af uafhængigt Cg-C3alkyl, Cg-C3fluoralkyl, Cg-C3alkoxy, Ci-C3fluoralkoxy, halogen, cyano eller nitro; heteroarylamino eller heteroarylamino, der er substitueret med 1, 2 eller 3 af uafhængigt Cg-C3alkyl, Cg-C3f luoralkyl, Cg- C3alkoxy, Ci-C3fluoralkoxy, halogen, cyano eller nitro; diheteroarylamino eller diheteroarylamino, der er substitueret med 1, 2 eller 3 af uafhængigt Cg-C3alkyl, Cg-C3fluoralkyl, cg-C3alkoxy, Ci-C3fluoralkoxy, halogen, cyano eller nitro; phenylamino eller phenylamino, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3fluoralkyl, Ci-C3alkoxy, Ci-C3fluoralkoxy, halogen, cyano eller nitro; diphenylamino eller diphenylamino, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3f luoralkyl, Ci-C3alkoxy, Ci- C3fluoralkoxy, halogen, cyano eller nitro; eller C3-Cvcycloalkylamino, di (C3-C7cycloalkyl) amino, C3-C7cycloalkoxy, Ci-Cioalkoxy, Ci-Ciofluoralkoxy, Ci-Csalkylamino eller di (Ci-C4alkyl)amino; Rf og Rg hver uafhængigt af hinanden er Ci-Cioalkyl, C2~ Cioalkenyl, C2-Cioalkynyl, Ci-Cioalkoxy, Ci-Ciof luoralkyl, Ci-Ciocyanoalkyl, Ci-Cionitroalkyl, Ci-Cioaminoalkyl, C3- C5alkylamino (C1-C5) alkyl, C2-C8dialkylamino (C1-C5) alkyl, C3- C7cycloalkyl (C1-C5) alkyl, Ci-Csalkoxy (C1-C5) alkyl, C3- Csalkenyloxy (C1-C5) alkyl, C3-Csalkynyloxy (C1-C5) alkyl, Ci~ Csalkylthio (C1-C5) alkyl, Ci-Csalkylsulfinyl (C1-C5) alkyl, Ci~ C5alkylsulfonyl (C1-C5) alkyl, C2-C8alkylidenaminoxy (C1-C5) alkyl, Ci-C5alkylcarbonyl (C1-C5) alkyl, Ci-Csalkoxycarbonyl (C1-C5) alkyl, aminocarbonyl (C1-C5) alkyl, Ci-Csalkylaminocarbonyl (C1-C5) alkyl, C2-C8dialkylaminocarbonyl (C1-C5) alkyl, Ci~ C5alkylcarbonylamino (C1-C5) alkyl, N- (C1-C5) alkylcarbonyl-N- (C2-C5) alkylaminoalkyl, C3-C6trialkylsilyl (C1-C5) alkyl, phenyl (Ci~ C5)alkyl (hvor phenyl eventuelt er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3f luoralkyl, Ci-C3alkoxy, Ci~ C3f luoralkoxy, Ci-C3alkylthio, Ci-C3alkylsulf inyl, Ci~ C3alkylsulfonyl, halogen, cyano eller nitro), heteroaryl(Ci— C5) alkyl (hvor heteroaryl eventuelt er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3fluoralkyl, Ci-C3alkoxy, Ci-C3fluoralkoxy, Ci-C3alkylthio, Ci-C3alkylsulfinyl, Ci~ C3alkylsulfonyl, halogen, cyano eller nitro), C2~ C5fluoralkenyl, C3-C8cycloalkyl; phenyl eller phenyl, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci~ C3fluoralkyl, Ci-C3alkoxy, Ci-C3fluoralkoxy, halogen, cyano eller nitro; heteroaryl eller heteroaryl, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3fluoralkyl, C3- C3alkoxy, Ci-C3fluoralkoxy, halogen, cyano eller nitro; heteroarylamino eller heteroarylamino, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3f luoralkyl, C3- C3alkoxy, Ci-C3fluoralkoxy, halogen, cyano eller nitro; diheteroarylamino eller diheteroarylamino, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3fluoralkyl, Ci-C3alkoxy, Ci-C3fluoralkoxy, halogen, cyano eller nitro; phenylamino eller phenylamino, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3fluoralkyl, Ci-C3alkoxy, Ci-C3fluoralkoxy, halogen, cyano eller nitro; diphenylamino eller diphenylamino, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3fluoralkyl, Ci-C3alkoxy, Ci- C3fluoralkoxy, halogen, cyano eller nitro; eller C3-Cvcycloalkylamino, di (C3-C7cycloalkyl)amino, C3-C7cycloalkoxy, Ci-Ciofluoralkoxy, Ci-Csalkylamino eller di (Ci-C4alkyl) amino; eller benzyloxy eller phenoxy, hvor benzyl- og phenylgrupperne for deres vedkommende eventuelt er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3fluoralkyl, Ci-C3alkoxy, Οχ-C3fluoralkoxy, halogen, cyano eller nitro; og Rh er Ci-Cioalkyl, C3-Ci0alkenyl, C3~Cioalkynyl, Ci-Ci0fluoralkyl, Ci-Ciocyanoalkyl, Ci-Ci0nitroalkyl, C2-Ci0aminoalkyl, Ci-C5alkylamino (C1-C5) alkyl, C2-C8dialkylamino (C1-C5) alkyl, C3- C7cycloalkyl (C1-C5) alkyl, Ci-Csalkoxy (Ci-C5) alkyl, C3- Csalkenyloxy (C1-C5) alkyl, C3-C5alkynyloxy (C1-C5) alkyl, Οχ- Csalkylthio (C1-C5) alkyl, Ci-C5alkylsulfinyl (C1-C5) alkyl, Οχ- Csalkylsulf onyl (C1-C5) alkyl, C2-C8alkylidenaminoxy (C1-C5) alkyl, Ci-Csalkylcarbonyl (C1-C5) alkyl, Ci-Csalkoxycarbonyl (C1-C5) alkyl, aminocarbonyl (C1-C5) alkyl, Ci-Csalkylaminocarbonyl (C1-C5) alkyl, C2-C8dialkylaminocarbonyl (C1-C5) alkyl, Cx- Csalkylcarbonylamino (C1-C5) alkyl, N- (C1-C5) alkylcarbonyl-W- (Cx-C5) alkylamino (C1-C5) alkyl, C3-Cstrialkylsilyl (C1-C5) alkyl, phenyl(C1-C5)alkyl (hvor phenyl eventuelt er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci~C3f luoralkyl, Ci~ C3alkoxy, Ci~C3fluoralkoxy, Ci-C3alkylthio, Ci-C3alkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano eller nitro), heteroaryl(Ci~ C5)alkyl (hvor heteroaryl eventuelt er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3fluoralkyl, Ci-C3alkoxy, Ci~C3fluoralkoxy, Ci-C3alkylthio, Ci-C3alkylsulfinyl, Οχ- C3alkylsulfonyl, halogen, cyano eller nitro), phenoxy(Ci-C5)alkyl (hvor phenyl eventuelt er substitueret med 1, 2 eller 3 af uafhængigt Ci~C3alkyl, Ci~C3f luoralkyl, Ci-C3alkoxy, Ci~ C3f luoralkoxy, Ci-C3alkylthio, Ci-C3alkylsulf inyl, Οχ- Caalkylsulfonyl, halogen, cyano eller nitro), heteroaryloxy(Ci-C5)alkyl (hvor heteroaryl eventuelt er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, Ci-C3fluoralkyl, Ci-C3alkoxy, Ci-C3fluoralkoxy, Ci-C3alkylthio, Ci-C3alkylsulfinyl, Ci~ Csalkylsulfonyl, halogen, cyano eller nitro), C3- Csfluoralkenyl, Cs-Cscycloalkyl; phenyl eller phenyl, der er substitueret med 1, 2 eller 3 af uafhængigt Ci-C3alkyl, CR- C3fluoralkyl, Ci-C3alkoxy, Ci-C3fluoralkoxy, halogen eller nitro; heteroaryl eller heteroaryl, der er substitueret med 1, 2 eller 3 af uafhængigt CR-Csalkyl, Ci-C3f luoralkyl, Ci- Csalkoxy, CR-Csfluoralkoxy, halogen, cyano eller nitro; eller phenyl-C(0)- eller Ci-C6alkyl-C(0)-; hvor "heteroaryl" betyder et aromatisk ringsystem, der indeholder mindst ét ringheteroatom og består enten af en enkelt ring eller af to fusionerede ringe; og hvor forbindelsen med formel (I) eventuelt er til stede som et agrokemisk acceptabelt salt deraf.
2. Forbindelse ifølge krav 1, hvor G er hydrogen; et landbrugsmæssigt acceptabelt metal eller en landbrugsmæssigt acceptabel sulfonium- eller ammoniumgruppe; eller G er -C (Xa) -Ra eller -C (Xb)-X°-Rb, hvor Xa, Ra, Xb, X° og Rb er som defineret i krav 1.
3. Forbindelse ifølge krav 1 eller 2, hvor, når G er -C (Xa)- Ra eller -C (Xb) -Xc-Rb, så er Xa, Xb og Xc oxygen, Ra er Ci-Cioalkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl eller Ci-C4alkoxyCi-C4alkyl; og Rb er Ci-Ci0alkyl, C2-C5alkenyl-CH2-, C2-C4alkenyl-CH (Me)-, C2-C5alkynyl-CH2-, C2-C4alkynyl-CH(Me)-, C3- C6cycloalkyl eller Ci-C4alkoxyCi-C4alkyl.
4. Forbindelse ifølge krav 1, 2 eller 3, hvor X er methyl.
5. Forbindelse ifølge et hvilket som helst af kravene 1 til 4, hvor R1 er methyl.
6. Forbindelse ifølge et hvilket som helst af kravene 1 til 5, hvor R2 er methyl.
7. Forbindelse ifølge et hvilket som helst af ovennævnte krav, hvor: R6 er Q-CH (R7) - eller Het-CH (R8) -; og R7 og R8 er hydrogen.
8. Forbindelse ifølge et hvilket som helst af ovennævnte krav, hvor Het er en eventuelt substitueret monocyklisk heteroaryl, der er bundet i et ringcarbon, som er: pyridinyl, pyrazolyl, imidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazolyl, tetrazol-5-yl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl eller oxadiazolyl; der eventuelt er til stede som et agrokemisk acceptabelt salt deraf.
9. Forbindelse ifølge et hvilket som helst af kravene 1 til 7, hvor Het er en eventuelt substitueret monocyklisk heteroaryl, der er bundet i et ringcarbon, som er: pyridin-2-yl, pyridin-3-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-2-yl, pyrazinyl, pyrimidin-4-yl eller pyridazin-3-yl; der eventuelt er til stede som et agrokemisk acceptabelt salt deraf.
10. Forbindelse ifølge et hvilket som helst af kravene 1 til 7, hvor Het er en eventuelt substitueret monocyklisk heteroaryl, der er bundet i et ringcarbon, som er: pyridin-2-yl eller pyrazol-3-yl; der eventuelt er til stede som et agrokemisk acceptabelt salt deraf.
11. Forbindelse ifølge et hvilket som helst af ovennævnte krav, hvor i Het et hvilket som helst ringcarbonatom, der er bundet direkte til ringatomet, som er koblingsstedet for -CH (R8)-delen, er usubstitueret.
12. Forbindelse ifølge et hvilket som helst af kravene 1 til 11, der er en forbindelse med formel (IC):
(IC), hvor X, R1, R2, R3, R4, R5, R6 og G er som defineret i et eller flere af kravene 1 til 11, og hvor mere end 50 % af molariteten af forbindelsen med formel (IC) har den anførte stereokemi i ringcarbonatomet, der er bundet til R5 og R6.
13. Herbicidsammensætning der omfatter: (i) en forbindelse med formel (I) som defineret i et hvilket som helst af kravene 1 til 12 og (ii) et agrokemisk acceptabelt bæremateriale, fortyndingsmiddel og/eller opløsningsmiddel; og (iii) eventuelt et eller flere yderligere herbicider og/eller eventuelt en safener.
14. Herbicidsammensætning ifølge krav 13, der omfatter en safener, hvor safeneren omfatter benoxacor, cloquintocetmexyl, cloquintocetsyre eller et agrokemisk acceptabelt salt deraf, cyprosulfamid, mefenpyrdiethyl og/eller N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl) amino]benzensulfonamid.
15. Fremgangsmåde til bekæmpelse af enkimbladet græsukrudt i afgrøder af nytteplanter, der omfatter påføring af en forbindelse med formel (I) som defineret i et hvilket som helst af kravene 1 til 12 eller en herbicidsammensætning, der omfatter en sådan forbindelse, som defineret i krav 13 eller 14, på planterne eller på voksestedet derfor.
DK12797857.5T 2011-11-30 2012-11-30 2-(substitueret phenyl)-cyclopentan-1,3-dionforbindelser og derivater deraf DK2785181T3 (da)

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HRP20161297T1 (hr) 2016-11-18
UA111869C2 (uk) 2016-06-24
EA027413B1 (ru) 2017-07-31
RS55269B1 (sr) 2017-02-28
PT2785181T (pt) 2016-10-25
ES2599807T3 (es) 2017-02-03
EP2785181A1 (en) 2014-10-08
ZA201403969B (en) 2015-05-27
EA201400622A1 (ru) 2014-11-28
EP2785181B1 (en) 2016-08-17
AU2012343771B2 (en) 2015-11-26
AR089051A1 (es) 2014-07-23
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BR112014013092A2 (pt) 2017-06-13
US9107415B2 (en) 2015-08-18
US20140323303A1 (en) 2014-10-30
UY34480A (es) 2013-06-28
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