Patent EP-0326330-A2 (EP)
Inventor: ARNOLD WENDELL RAY
IPC: A01N55/10
Filed: 1989-01-25
Abstract: Quinoline, quinazoline, and cinnoline fungicides. 
     Compounds of the formula (1)
     wherein
     X is CR 5  or N, where R 5  is H, Cl, or CH 3 ;   Y is CR 5 ' if X is N, and Y is CR 5 ' or N if X is CR S , where R 5 ' is H, Cl, or Br;   Z is 0, S, SO, S0 2 , NR 6 , where R 6  is H, (C 1 -C 4 ) alkyl, or (C 1 -C 4 ) acyl, or CR 7 R 8 , where R 7  and R 8  are independently H, (C 1 -C 4 ) acyl, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkenyl, (C 2 -C 4 ) 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, NO 2 , halo, I, (C 1 -C 4 ) alkyl, (C 3 -C 4 ) branched alkyl, (C 1 -C 4 ) alkoxy, halo (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkoxy, or halo (C 1 -C 4 ) 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 C 1 -C 18  saturated or unsaturated hydrocarbon chain, straight chain or branched, optionally including a hetero atom selected from 0, S, SO, S0 2 , or Si, and optionally substituted with halo, halo (C 1 -C 4 ) alkoxy, hydroxy, or (C 1 -C 4 ) acyl;   (b) (C 3 -C 8 ) cycloalkyl or cycloalkenyl;   (c) a phenyl group of the formula (2)
     wherein R 9  to R 13  are independently
   H,   CN,   N0 2 ,   OH,   halo,   I,   (C 1 -C 4 ) alkyl,   (C 3 -C 4 ) branched alkyl,   (C 2 -C 4 ) acyl,   halo (C I -C 4 ) alkyl,   hydroxy (C 1 -C 4 ) alkyl,   (C 1 -C 4 ) alkoxy,   halo (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio,   halo (C 1 -C 4 ) alkylthio,   phenyl,   substituted phenyl,   phenoxy,   substituted phenoxy,   phenylthio,   substituted phenylthio,   phenyl (C 1 -C 4 ) alkyl,   substituted phenyl (C 1 -C 4 ) alkyl,   benzoyl,   substituted benzoyl,   SiR 20 R 21 R 22  or OSiR 20 R 21 R 22 , where  R20, R21,  and R 22  are H, a C 1 -C 6  alkyl group, straight chain or branched, phenyl, or substituted phenyl, provided that at least one of R 20 , R 21 , and R 22  is other than H, or R 11  and R 12  or R 12  and R 13  combine to form a carbocyclic ring, provided that unless all of R 9  to R 13  are H or F, then at least two of R 9  to R 13  are H;       (d) a furyl group of formula (3)
     wherein R 14  is H, halo, halomethyl, CN, N0 2 , (C 1 -C 4 ) alkyl, (C 3 -C 4 ) branched alkyl, phenyl, or (C 1 -C 4 ) alkoxy,   (e) a thienyl group of formula (4)
     wherein R 15  is H, halo, halomethyl, CN, N0 2 , (Ci-C4) alkyl, (C 3 -C 4 ) branched alkyl, phenyl, or (C 1 -C 4 ) alkoxy;   (f) a group of formula (5) or (5a)
     wherein R 16  is H, halo, halomethyl, CN, N0 2 , (C 1 -C 4 ) alkyl, (C 3 -C 4 ) branched alkyl, phenyl, substituted phenyl, or (C 1 -C 4 ) alkoxy, and F is N or CH and G is 0, NR 19  or CH, provided that either F is N or G is NR 19 , where R 19  is H, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) 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 S0 2  if A is a group described in paragraph (a), are plant fungicides.