Patent EP-0326330-B1 (EP)
Inventor: ARNOLD WENDELL RAY
IPC: A01N55/10
Filed: 1989-01-25
Granted: 2002-07-24
Abstract: Compounds of the formula (1) <CHEM>  wherein  X is CR<5> or N, where R<5> is H, Cl, or CH3; Y is CR<5> min  if X is N, and Y is CR<5> min  or N if X is CR<5>, where R<5> min  is H, Cl, or Br; Z is O, S, SO, SO2, NR<6>, where R<6> is H, (C1-C4) alkyl, or (C1-C4) acyl, or CR<7>R<8>, where R<7> and R<8> are independently H, (C1-C4) acyl, (C1-C4) alkyl, (C1-C4) alkenyl, (C2-C4) alkynyl, CN, or OH, or R<7> and R<8> combine to form a carbocyclic rirg containing four to six carbon atoms; R<1> to R<4> 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 R<1> and R<2> or R<2> and R<3> 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 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 or cycloalkenyl;   (c) a phenyl group of the formula (2) <CHEM>  wherein R<9> to R<1><3> are independently  H,  CN,  NO2,  OH,  halo,  I,  (C1-C4) alkyl,  (C3-C4) branched alkyl,  (C2-C4 ) acyl,  halo (C1-C4) alkyl,  hydroxy (C1-C4) alkyl,  (C1-C4) alkoxy,  halo (C1-C4) alkoxy, (C1-C4) alkylthio,  halo (C1-C4) alkylthio,  phenyl,  substituted phenyl,  phenoxy,  substituted phenoxy,  phenylthio,  substituted phenylthio,  phenyl (C1-C4) alkyl,  substituted phenyl (C1-C4) alkyl,  benzoyl,  substituted benzoyl, SiR<2><0>R<2><1>R<2><2> or OSiR<2><0>R<2><1>R<2><2>, where R<2><0>, R<2><1>, and R<2><2> are H, a C1-C6 alkyl group, straight chain or branched, phenyl, or substituted phenyl, provided that at least one of R<2><0>, R<2><1>, and R<2><2> is other than H, or R<1><1> and R<1><2> or R<1><2> and R<1><3> combine to form a carbocyclic ring, provided that unless all of R<9> to R<1><3> are H or F, then at least two of R<9> to R<1><3> are H;   (d) a furyl group of formula (3) <CHEM> wherein R<1><4> is H, halo, halomethyl, CN, NO2, (C1-C4) alkyl, (C3-C4) branched alkyl, phenyl, or (C1-C4) alkoxy,   (e) a thienyl group of formula (4) <CHEM> wherein R<1><5> 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) <CHEM> wherein R<1><6> 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, NR<1><9> or CH, provided that either F is N or G is NR<1><9>, where R<1><9> is H, (C1-C4) alkyl, (C1-C4) acyl, phenylsulfonyl, or substituted phenylsulfonyl;   (g) a group selected from  1-naphthyl,  substituted 1-naphthyl,  4-pyrazolyl,  3-methyl-4-pyrazolyl,  1,3-benzodioxolyl,  tricyclo[3.3.1.1(3,7)]dec-2-yl,  1-(3-chlorophenyl)-1H-tetrazol-5-yl,  pyridyl,  pyridazinyl, 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 CR<7>R<8> 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), are plant fungicides. o