Quinoline derivatives

A compound formula ##STR16## wherein R.sup.1 to R.sup.4 are independently:

• H, halo, (C.sub.1 -C.sub.4) alkyl, branched (C.sub.3 -C.sub.4) alkyl, halo (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, halo (C.sub.1 -C.sub.4) alkoxy, NO.sub.2, or NH.sub.2, at least two of R.sup.1 to R.sup.4 being H,
• both X and Y are CR.sup.5,
• R.sup.5 is H, CH.sub.3, or Cl;
• Z is 0, NR.sup.6, or CR.sup.7 R.sup.8 ;
• R.sup.6 is H, (C.sub.1 -C.sub.4) alkyl, or (C.sub.2 -C.sub.4) acyl,
• R.sup.7 and R.sup.8 are independently H, (C.sub.1 -C.sub.4) alkyl, branched (C.sub.3 -C.sub.4) alkyl, or (C.sub.1 -C.sub.4) acyl, or R.sup.7 and R.sup.8 combine to form a saturated or unsatured carbocyclic ring containing three to seven carbon atoms, or one or both of R.sup.7 and R.sup.8 can combine with one or both of R.sup.9 and R.sup.10 to form a multiple bond;
• R.sup.9 and R.sup.10 are independently H, (C.sub.1 -C.sub.3) alkyl, phenyl, substituted phenyl, (C.sub.3 -C.sub.8) cycloalkyl, hydroy, halo, or acetyl, or R.sup.9 and R.sup.10 combine to form a saturated or unsaturated carbocyclic ring containing three to seven carbon atoms;
• and
• Ar is
• (C.sub.3 -C.sub.8) cycloalkyl,
• substituted (C.sub.3 -C.sub.8) cycloalkyl,
• (C.sub.3 -C.sub.8) cycloalkenyl,
• naphthyl,
• dihydronaphthyl,
• tetrahydronaphthyl,
• decahydronaphthyl,
• 1. 3-benzodioxolyl,
• fluorenyl,
• pyridyl
• substituted pyridyl,
• 2,3-dihydro-1,4-benzodioin-2-yl,
• furyl optionally substituted with halo, CF.sub.3, CN, NO.sub.2, (C.sub.1 -C.sub.4) alkyl, branched (C.sub.3 -C.sub.4) alkyl, phenyl, or (C.sub.1 -C.sub.4) alkoy,
• thienyl optionally substituted with halo, CF.sub.3, CN, NO.sub.2, (C.sub.1 -C.sub.4) alkyl, branched (C.sub.3 -C.sub.4) alkyl, phenyl, or (C.sub.1 -C.sub.4) alkoxy,
• a group of the formula (2) or (2a) ##STR17## wherein R.sup.11 is H, halo, CF.sub.3, CN, NO.sub.2, (C.sub.1 -C.sub.4) alkyl, branched (C.sub.3 -C.sub.4) alkyl, phenyl, or (C.sub.1 -C.sub.4) alkoxy, M is N or CH and G is O, NR.sup.20, or CH.sub.2, provided that M is N or G is NR.sup.20, where R.sup.20 is H, (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) acyl, phenylsulfonyl, or substituted phenylsulfonyl;
• a group of the formula (3) ##STR18## wherein R.sup.12 to R.sup.16 are independently H, halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio, or substituted phenylthio, NO.sub.2, NH.sub.2, acetoy, OH, CN, or SiR.sup.17 R.sup.18 R.sup.19, or OSiR.sup.17 R.sup.18 R.sup.19, where R.sup.17, R.sup.18, or R.sup.19 are independently C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 branched alkyl, phenyl, or substituted phenyl, provided that unless each of R.sup.12 to R.sup.16 is F, CH.sub.3, or H, then at least two of R.sup.12 to R.sup.16 are H;
• or an acid addition salt of a compound of formula (1), or an N-oxide of a compound of formula (1) where Y is CR.sup.5 ;
• wherein, as used above, the term "substituted phenyl" refers to phenyl substituted with up to three groups independently selected from halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, hydroxy (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, phenyl, NO.sub.2, OH, CN, (C.sub.1 -C.sub.4) alkanoyloxy, or benzoyloxy;
• "substituted phenoxy" refers to phenoxy substituted with up to three groups independently selected from halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, hydroxy (C.sub.1 -C.sup.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, phenyl, NO.sub.2, OH, CN, (C.sub.1 -C.sub.4) alkanoyloxy, or benzoyloxy;
• "substituted phenylthio" refers to phenylthio substituted with up to three groups independently selected from halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, hydroxy (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, phenyl, NO.sub.2, OH, CN, (C.sub.1 -C.sub.4) alkanoyloxy, or benzoyloxy;
• "substituted phenylsulfonyl" refers to phenylsulfonyl substituted with up to three groups independently selected from halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, hydroy (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, phenyl, NO.sub.2, OH, CN, (C.sub.1 -C.sub.4) alkanoyloxy, or benzoyloxy;
• "substituted (C.sub.3 -C.sub.8) cycloalkyl" refers to a (C.sub.3 -C.sub.8) cycloalkyl group substituted with up to three groups independently selected from halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, hydroxy (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, phenyl, NO.sub.2, OH, CN, (C.sub.1 -C.sub.4) alkanoyloxy, or benzoyloxy;
• and
• "substituted pyridyl" refers to a pyridyl group substituted with halo, halomethyl, CN, NO.sub.2, (C.sub.1 -C.sub.4) alkyl, (C.sub.3 -C.sub.4) branched alkyl, phenyl, (C.sub.1 -C.sub.7) alkoxy, or halo (C.sub.1 -C.sub.7) alkoxy;
• provided that
• if X and Y are CR.sup.5 and Z is NR.sup.6, then R.sup.4 is Cl or F, or Ar is a group of formula (3) wherein one of R.sup.12 to R.sup.16 is substituted phenyl, phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, halo (C.sub.1 -C.sub.4)alkyl, or halo (C.sub.1 -C.sub.4) alkoxy,
• Ar is not 5-nitro-2-furyl.
• provided further that
• 4-benzoxyquinoine and its N-oxide are excluded.

A compound of formula (1) ##STR19## wherein R.sup.1 to R.sup.4 are independently:

• H, halo, (C.sub.1 -C.sub.4) alkyl, branched (C.sub.3 -C.sub.4) alkyl, halo (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, halo (C.sub.1 -C.sub.4) alkoxy, NO.sub.2, or NH.sub.2, at least two of R.sup.1 to R.sup.4 being H,
• X and Y are CR.sup.5,
• R.sup.5 is H, CH.sub.3, or Cl;
• Z is 0, NR.sup.6, or CR.sup.7 R.sup.8 ;
• R.sup.6 is H, (C.sub.1 -C.sub.4) alkyl, or (C.sub.2 -C.sub.4) acyl,
• R.sup.7 and R.sup.8 are independently H, (C.sub.1 -C.sub.4) alkyl, branched (C.sub.3 -C.sub.4) alkyl, or (C.sub.1 -C.sub.4) acyl, or R.sup.7 and R.sup.8 combine to form a saturated or unsatured carbocyclic ring containing three to seven carbon atoms, or one or both of R.sup.7 and R.sup.8 can combine with one or both of R.sup.9 and R.sup.10 to form a multiple bond;
• R.sup.9 and R.sup.10 are independently H, (C.sub.1 -C.sub.3) alkyl, phenyl, substituted phenyl, (C.sub.3 -C.sub.8) cycloalkyl, hydroy, halo, or acetyl, or R.sup.9 and R.sup.10 combine to form a saturated or unsaturated carbocyclic ring containing three to seven carbon atoms;
• and
• Ar is
• (C.sub.3 -C.sub.8) cycloalkyl,
• substituted (C.sub.3 -C.sub.8) cycloalkyl,
• (C.sub.3 -C.sub.8) cycloalkenyl,
• naphthyl,
• dihydronaphthyl,
• tetrahydronaphthyl,
• decahydronaphthyl,
• 1. 3-benzodioxolyl,
• fluorenyl,
• pyridyl
• substituted pyridyl,
• 2,3-dihydro-1,4-benzodioin-2-yl,
• furyl optionally substituted with halo, CF.sub.3, CN, NO.sub.2, (C.sub.1 -C.sub.4) alkyl, branched (C.sub.3 -C.sub.4) alkyl, phenyl, or (C.sub.1 -C.sub.4) alkoy,
• thienyl optionally substituted with halo, CF.sub.3, CN, NO.sub.2, (C.sub.1 -C.sub.4) alkyl, branched (C.sub.3 -C.sub.4) alkyl, phenyl, or (C.sub.1 -C.sub.4) alkoxy,
• a group of the formula (2) or (2a) ##STR20## wherein R.sup.11 is H, halo, CF.sub.3, CN, NO.sub.2, (C.sub.1 -C.sub.4) alkyl, branched (C.sub.3 -C.sub.4) alkyl, phenyl, or (C.sub.1 -C.sub.4) alkoxy, M is N or CH and G is O, NR.sup.20, or CH.sub.2, provided that M is N or G is NR.sup.20, where R.sup.20 is H, (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) acyl, phenylsulfonyl, or substituted phenylsulfonyl;
• a group of the formula (3) ##STR21## wherein R.sup.12 to R.sup.16 are independently H, halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio, or substituted phenylthio, NO.sub.2, NH.sub.2, acetoxy, OH, CN, or SiR.sup.17 R.sup.18 R.sup.19, or OSiR.sup.17 R.sup.18 R.sup.19, where R.sup.17, R.sup.18, or R.sup.19 are independently C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 branched alkyl, phenyl, or substituted phenyl, provided that unless each of R.sup.12 to R.sup.16 is F, CH.sub.3, or H, then at least two of R.sup.12 to R.sup.16 are H;
• or an acid addition salt of a compound of formula (1), or an N-oxide of a compound of formula (1),
• wherein, as used above, the term "substituted phenyl" refers to phenyl substituted with up to three groups independently selected from halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, hydroxy (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, phenyl, NO.sub.2, OH, CN, (C.sub.1 -C.sub.4) alkanoyloxy, or benzoyloxy;
• "substituted phenoxy" refers to phenoxy substituted with up to three groups independently selected from halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, hydroxy (C.sub.1 -C.sup.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, phenyl, NO.sub.2, OH, CN, (C.sub.1 -C.sub.4) alkanoyloxy, or benzoyloxy;
• "substituted phenylthio" refers to phenylthio substituted with up to three groups independently selected from halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, hydroxy (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, phenyl, NO.sub.2, OH, CN, (C.sub.1 -C.sub.4) alkanoyloxy, or benzoyloxy;
• "substituted phenylsulfonyl" refers to phenylsulfonyl substituted with up to three groups independently selected from halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, hydroy (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, phenyl, NO.sub.2, OH, CN, (C.sub.1 -C.sub.4) alkanoyloxy, or benzoyloxy;
• "substituted (C.sub.3 -C.sub.8) cycloalkyl" refers to a (C.sub.3 -C.sub.8) cycloalkyl group substituted with up to three groups independently selected from halo, (C.sub.1 -C.sub.10) alkyl, branched (C.sub.3 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.7) alkyl, hydroxy (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, phenyl, NO.sub.2, OH, CN, (C.sub.1 -C.sub.4) alkanoyloxy, or benzoyloxy;
• and
• "substituted pyridyl" refers to a pyridyl group substituted with halo, halomethyl, CN, NO.sub.2, (C.sub.1 -C.sub.4) alkyl, (C.sub.3 -C.sub.4) branched alkyl, phenyl, (C.sub.1 -C.sub.7) alkoxy, or halo (C.sub.1 -C.sub.7) alkoxy;
• provided that
• if X and Y are CR.sup.5 and Z is NR.sup.6, then R.sup.4 is Cl or F, or Ar is a group of formula (3) wherein one of R.sup.12 to R.sup.16 is substituted phenyl, phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, halo (C.sub.1 -C.sub.4)alkyl, or halo (C.sub.1 -C.sub.4) alkoxy,
• Ar is not 5-nitro-2-furyl.
• at least one of the following conditions is satisfied:
• (1) Z is CR.sup.7 R.sup.8 ;
• (2) R.sup.3 is Cl and R.sup.1, R.sup.2, and R.sup.4 are H;
• (3) R.sup.9 is CH.sub.3 and R.sup.10 is H;
• (4) Ar is a group of formula (3) wherein at least one of R.sup.12 to R.sup.16 is F;
• (5) Ar is a group of formula (3) wherein at least one of R.sup.12 to R.sup.16 is CF.sub.3 ;
• (6) Ar is a group of formula (3) wherein at least one of R.sup.12 to R.sup.16 is (C.sub.1 -C.sub.4 alkoxy);
• (7) Ar is a group of formula (3) wherein at least one of R.sup.12 to R.sup.16 is halo (C.sub.1 -C.sub.4 alkoxy).