Patent EP-0414386-A1 (EP)
Inventor: HACKLER RONALD ERVIN
IPC: C07D475/06
Filed: 1990-07-26
Abstract: Compounds of the formula (1):
      wherein 
one or two of A, B, E, or D are N, and the others are CR¹ or A, E, and D are N and B is CR¹; where R¹ and R² are independently H, halo, (C₁-C₄) alkyl, (C₃-C₄) branched alkyl, (C₁-C₄) alkoxy, halo (C₁-C₄) alkyl, phenyl, or substituted phenyl; 
X is O, S, SO, SO₂, NR³, or CR⁴R⁵, where R³ is H, (C₁-C₄) alkyl, or (C₁-C₄) acyl, and R⁴ and R⁵ are in­dependently H, (C₁-C₄) acyl, (C₁-C₄) alkyl, (C₂-C₄) alk­enyl or -alkynyl, CN, or OH, or R⁴ and R⁵ combine to form a carbocyclic ring containing four to six carbon atoms; 
Y is a bond or an alkylene chain one to six carbon atoms long, optionally including a carbocyclic ring, and optionally including a hetero atom selected from O, NR³, S, SO, SO₂, or SiR²⁰R²¹, where R³ is as de­fined above and R²⁰ and R²¹ are independently (C₁-C₄) alkyl, (C₃-C₄) branched alkyl, phenyl, or substituted phenyl, and optionally substituted with (C₁-C₄) alkyl, (C₂-C₄) alkenyl or -alkynyl, branched (C₃-C₇) alkyl, (C₃-C₇) cycloalkyl or -cycloalkenyl, halo, hydroxy, or acetyl, and 
Z is  
     (a) a C₁-C₁₂ saturated or unsaturated hydro­carbon chain, straight chain or branched optionally in­cluding a hetero atom selected from O, S, SO, SO₂, or SiR²⁰R²¹, where R²⁰ and R²¹ are as defined above, and optionally substituted with halo, halo (C₁-C₄) alkoxy, hydroxy, (C₃-C₈) cycloalkyl or cycloalkenyl, or (C₁-C₄) acyl;   (b) (C₃-C₈) cycloalkyl or cycloalkenyl, option­ally substituted with (C₁-C₄) alkyl, (C₁-C₄) alkoxy, halo (C₁-C₄) alkyl, halo (C₁-C₄) alkoxy, halo, hydroxy, or (C₁-C₄) acyl;   (c) a phenyl group of the formula (2)
      where 
R⁶ to R¹⁰ are independently H. halo, I, (C₁-C₁₀) alkyl, (C₃-C₈) alkenyl or -alkynyl, branched (C₃-C₆) alkyl, -alkenyl, or -alkynyl, (C₃-C₈) cycloalkyl or -cycloalkenyl, ha]o (C₁-C₇) alkyl, (C₁-C₇) alkoxy, (C₁-C₇) alkylthio, halo (C₁-C₇) alkoxy, phenoxy, substituted phenoxy, phenyl­thio, substituted phenylthio, phenyl, substituted phenyl, NO₂, acetoxy, OH, CN, SiR¹¹R¹²R¹³, OSiR¹¹R¹²R¹³, NR¹⁴R¹⁵, S(O)R¹⁶, or SO₂R¹⁷ where R¹¹, R¹², and R¹³ are independ­ently (C₁-C₄) alkyl, (C₃-C₄) branched alkyl, phenyl, or substituted phenyl, R¹⁴ and R¹⁵ are independently H, (C₁-C₄) alkyl, or (C₁-C₄) acyl, and R¹⁶ and R¹⁷ are (C₁-C₁₀) alkyl, phenyl, or substituted phenyl;     (d) a furyl group of formula (3)
      where R¹⁸ is H, halo, halomethyl, CN, NO₂, (C₁-C₄) alkyl, (C₃-C₄) branched alkyl, phenyl, or (C₁-C₄) alkoxy;   (e) a thienyl group of the formula (4)
      where R¹⁸ is as defined in paragraph (d);   (f) a group of formula (5) or (6)
      where R¹⁸ is as defined in paragraph (d), J is N or CH, and G is O, NR¹⁹, or S, provided that if J is not N then G is NR¹⁹, where R¹⁹ is H, (C₁-C₄) alkyl, (C₁-C₄) acyl, phenylsulfonyl, or substituted phenylsulfonyl;   (g) a group selected from 
optionally substituted naphthyl, dihydro­naphthyl, tetrahydronaphthyl, and decahydronaphthyl; 
optionally substituted pyridyl; 
optionally substituted indolyl; 
  and 1,3-benzodioxolyl; 
or an acid addition salt of a compound of formula (1)    are plant fungicides, miticides, and insecticides.