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Quinoline, Quinazoline, and Cinnoline Fungicides

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Quinoline, Quinazoline, and Cinnoline Fungicides Europaisches Patentamt J) European Patent Office (ti) Publication number: 0 326 33a Office europeen des brevets A2 EUROPEAN PATENT APPLICATION @ Application number: 89300658.5 mtci.*: C 07 D 215/22 C 07 D 215/60, @ Date of filing: 25.01.89 C 07 D 401/12, C 07 D 215/18, C 07 D 215/42, C 07 D 239/94, C 07 D 239/88, C 07 D 239/74, C 07 D 237/28, A 01 N 43/54, A 01 N 43/42 © Priority: 29.01.88 US 150266 Coghlan, Michael Joseph 5744 Cricket Ridge (43) Date of publication of application: Indianapolis Indiana 46250 (US) 02.08.89 Bulletin 89/31 Krumkalns, Eriks Victor 6333 North Rural @ Designated Contracting States : Indianapolis Indiana 46220 (US) AT BE CH DE ES FR GB GR IT LI LU NL SE Jourdan, Glen Phil © Applicant: ELI LILLY AND COMPANY R.R. Nr.1 Box74B Lilly Corporate Center Morristown Indiana 46161 (US) Indianapolis Indiana 46285 (US) Suhr, Robert George 1522 Bruner Drive @ Inventor: Arnold, Wendell Ray Greenfield Indiana 46140 (US) 11803 Eden Glen Drive Carmel Indiana 46032 (US) (74) Representative: Tapping, Kenneth George et al Erl Wood Manor Windlesham Surrey, GU20 6PH (GB) Claims for the following Contracting State: ES. © Quinoline, quinazoline, and cinnoline fungicides. (57) Compounds of the formula (1) acyl, or CR7R8, where R7 and R8 are independently H, (C1-C4) acyl, (C1-C4) alkyl, (C1-C4) alkenyl, (C2-C4) alkynyl, CN, or OH, or R7 and R8 combine to form a carbocyclic rirg containing four Z — A to six carbon atoms; R1 to R4 are independently H, OH, NO2, halo, I, (C1-C4) alkyl, (C3-C4) branched alkyl, (C1-C4) alkoxy, halo (C1-C4) alkyl, halo CM (C1-C4) alkoxy, or halo (C1-C4) alkylthio; or R1 and R2 or R2 and < R3 combine to form a carbocyclic ring containing 4 to 6 carbon (1) atoms; O A is CO ^X CO R3 N (a) a C1-C18 saturated or unsaturated hydrocarbon chain, straight chain or branched, optionally including a <o hetero atom selected from O, S, SO, SO2, or Si, and CM optionally substituted with halo, halo (C1-C4) alkoxy, CO hydroxy, or (C1-C4) acyl; wherein (b) (C3-C8) cycloalkyl orcycloalkenyl; (c) a of the formula (2) X is CR5 or N, where R5 is H, Cl, or CH3; phenyl group CL Y is CR5' if X is N, and Y is CR5' or N if X is CR5, where R5' is H, LLl Cl, or Br; Z is O, S, SO, SO2, NR6, where R6 is H, (C1-C4) alkyl, or (C1-C4) Bundesdruokerei Berlin (5a) (2) wherein R16 is H, halo, halomethyl, CN, NO2, (C1-C4) alky!, (C3-C4) branched alkyl, phenyl, substituted phenyl, or (C1-C4) alkoxy, and F is N or CH and G is O, NR19 or CH, provided that either F is N or G is NR19, where R19 is H, wherein R9 to R13 are independently (C1-C4) alkyl, (C1-C4) acyl, phenylsulfonyl, or substituted H, phenylsulfonyl; CN, (g) a group selected from NO2, 1-naphthyl, OH, substituted 1-naphthyl, halo, 4-pyrazolyl, I, 3-methyl-4-pyrazolyl, (C1-C4) alkyl, 1 ,3-benzodioxolyl, (C3-C4) branched alkyl, tricyclo[3.3.1.1(3,7)]dec-2-yl, (C2-C4 ) acyl, 1-(3-chlorophenyl)-1H-tetrazol-5-yl, halo (C1-C4) alkyl, pyridyl, hydroxy (C1-C4) alkyl, pyridazinyl, (C1-C4) alkoxy, or an acid addition salt of a compound of formula (1 ) , or an halo (C1-C4) alkoxy, (C1-C4) alkylthio, N-oxide of a compound of formula (1) where Y is CH; halo(Ci-C4)alkylthio, provided Z is CR7R8 if A is a group described in paragraph phenyl, (d) , (e) , or (f ) ; and provided that Z is S, SO, or SO2 if A is a substituted phenyl, group described in paragraph (a), are plant fungicides. phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, phenyl (C1-C4) alkyl, substituted phenyl (C1-C4) alkyl, benzoyl, substituted benzoyl, SiR20R21R22 or OSiR20R21R22, where R20, R21, and R22 are H, a C1-C6 alkyl group, straight chain or branched, phenyl, or substituted phenyl, provided that at least one of R20. R21, and R22 is other than H, or R11 and R12 or R12 and R13 combine to form a carbocyclic ring, provided that unless all of R9 to R13 are H or F, then at least two of R9 to R13areH; (d) afuryl group of formula (3) wherein R14 is H, halo, halomethyl, CN, NO2, (C1-C4) alkyl, (C3-C4) branched alkyl, phenyl, or (C1-C4) alkoxy, fe) athienyl group of formula (4) tr (4) wherein R15 is H, halo, halomethyl, CN, NO2, (C1-C4) alkyl, (C3-C4) branched alkyl, phenyl, or (C1-C4) alkoxy; (f ) a group of formula (5) or (5a) EP 0 326 330 A2 Description QUINOLINE, QUINAZOLINE, AND CINNOLINE FUNGICIDES 5 Background of the Invention Field of the Invention This invention provides new compounds that have excellent plant fungicide activity. Some of the 10 compounds have also demonstrated insecticidal and miticidal activity. The invention also provides compositions and combination products that contain a compound of the invention as active ingredient. Some of the combination products have shown synergistic activity against plant pathogens. The invention also provides fungicidal methods. There is an acute need for new fungicides, because target pathogens are rapidly developing resistance to 15 known fungicides. Widespread failure of N-substituted azole fungicides to control barley mildew was observed in 1983, and has been attributed to the development of resistance. The field performance of DMI (demethylation inhibitor) fungicides, which are now widely relied on to protect cereal crops from powdery mildew, has declined since they were introduced in the 1970's. Similarly, the pathogen population responsible for grape Botrytis, the number one disease in grapes as well as in berry crops and in tomato and cucumber 20 greenhouse crops, has shifted to strains that are resistant to benzimidazole and dicarboximide fungicides. Summary of the Invention This invention provides a fungicidal method which comprises applying to the locus of the fungus a fungicidally effective amount of a compound of the formula (1) 25 R1 Z — A wherein 40 X is CR5 or N, where R5 is H, Cl, or CH3; Y is CR5 if X is N, and Y is CR5' or N if X is CR5', where R5' is H, Cl, or Br; Z is O, S, SO, SO2, NR6, where R6 is H, (C1-C4) alkyl, or (C1-C4) acyl, or CR7R8, where R7 and R8 are independently H, (C1-C4) acyl, (C1-C4) alkyl, (C1-C4) alkenyl, (C2-C4) alkynyl, CN, or OH, or R7 and R8 combine to form a carbocyclic ring containing four to six carbon atoms; 45 R1 to R4 are independently H, OH, NO2, halo, I, (C1-C4) alkyl, (C3-C4) branched alkyl, (C1-C4) alkoxy, halo (C1-C4) alkyl, halo (C1-C4) alkoxy, or halo (C1-C4) alkylthio; or R1 and R2 or R2 and R3 combine to form a carbocyclic ring containing 4 to 6 carbon atoms; A is (a) a C1-C18 saturated or unsaturated hydrocarbon chain, straight chain or branched, optionally SO including a hetero atom selected from O, S, SO, SO2, or Si, and optionally substituted with halo, halo (C1-C4) alkoxy, hydroxy, or (C1-C4) acyl; (b) (C3-C8) cycloalkyl orcycloalkenyl; (c) a phenyl group of the formula (2) 55 60 EP 0 326 330 A2 (2) 10 wherein R9 to R13 are independently H, CN, 15 NO2, OH, halo, I, (Ci-C4)alkyl, 20 (C3-C4) branched alkyl, (C2-C4) acyl, halo (C1-C4) alkyl, hydroxy(Ci-C4) alkyl, (C1-C4) alkoxy, 25 halo(Ci-C4) alkoxy, (C1-C4) aikylthio, halo(Ci-C4)alkylthio, phenyl, substituted phenyl, 30 phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, phenyl (C1-C4) alkyl, 35 substituted phenyl (C1-C4) alkyl, benzoyl, substituted benzoyl, SiR20R21R22 or OSiR20R21 R22, where R20, R21, and R22 are H, a Ci-C6 alkyl group, straight chain or branched, phenyl, or substituted phenyl, provided that at least one of R20, R21 , and R22 is other than H, or R11 and R12 or R12 and R13 combine to form acarbocyclic ring, provided that unless all of R9 to R13 are H 40 or F, then at least two of R9 to R13 are H ; (d) afuryl group of formula (3) ' R14 ' 45 50 wherein R14 is H, halo, halomethyl, CN, NO2, (C1-C4) alkyl, (C3-C4) branched alkyl, phenyl, or (C1-C4) alkoxy, (e) athienyl group of formula (4) 55 60 wherein R15 is H, halo, halomethyl, CN, NO2, (C1-C4) alkyl, (C3-C4) branched alkyl, phenyl, or (C1-C4) alkoxy; 65 EP 0 326 330 A2 (f) a group of formula (5) or (5a) 10 wherein R16 is H, halo, halomethyl, CN, NO2, (C1-C4) alkyl, (C3-C4) branched alkyl, phenyl, substituted phenyl, or (C1-C4) alkoxy, and F is N or CH and G is O, NR19 or CH, provided that either F is N or G is NR19, where R19 is H, (C1-C4) alkyl, (C1-C4) acyl, phenylsulfonyl, or substituted phenylsulfonyl; 15 (g) a group selected from 1-naphthyl, substituted 1-naphthyl, 4-pyrazolyl, 3-methyl-4-pyrazolyl, 20 1,3-benzodioxolyl, tricyclo[3.3.1.1(3,7)]dec-2-yl, 1-(3-chlorophenyl)-1H-tetrazol-5-yl, pyridyl, pyridazinyl, 25 or an acid addition salt of a compound of formula (1), or an N-oxide of a compound of formula (1) where Y is CH; provided Z is CR7R8 if A is a group described in paragraph (d), (e), or (f); and provided that Z is S, SO, or SO2 if A is a group described in paragraph (a) .
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