1. Patent Search
  2. Details

AZOLOBENZAZINE COMPOUNDS, COMPOSITIONS COMPRISING THESE COMPOUNDS AND THEIR USE FOR CONTROLLING INVERTEBRATE PESTS

20180002346 · 2018-01-04

    Inventors

    Cpc classification

    International classification

    Abstract

    Azolobenzazine compounds of the formula I and N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof are disclosed, as well as are methods for controlling invertebrate pests using the disclosed compounds. Further disclosed are plant propagation materials, agricultural compositions, and veterinary compositions that include the disclosed compounds.

    ##STR00001##

    Claims

    1. Compounds of formula I; ##STR00079## wherein C.sup.1 is C or CH; C.sup.2 is C or CH; A.sup.1 is N or C; A.sup.2 is N, C(R.sup.2), N(R.sup.3), O, S or C(R.sup.4,R.sup.5); A.sup.3 is N, O, S, N(R.sup.6), C(R.sup.7) or C(R.sup.8,R.sup.9); A.sup.4 is N or C(R); A.sup.5 is N or C(R); A.sup.6 is N or C(R); wherein one or two non-adjacent bonds in the 5-membered ring formed by C.sup.1, C.sup.2, A.sup.1, A.sup.2 and A.sup.3 are double bonds, while the others are single bonds, provided that the bond between A.sup.1 and A.sup.2 or the bond between A.sup.1 and C.sup.1 or the bond between A.sup.2 and A.sup.3 or the bond between C.sup.1 and C.sup.2 or the bond between A.sup.3 and C.sup.2 is a double bond further provided that at least one of A.sup.1, A.sup.2 and A.sup.3 is N, N(R.sup.3) or N(R.sup.6), provided that 1 or 2 of A.sup.4, A.sup.5 and A.sup.6 is N; and wherein R.sup.2, R.sup.7 independently of each other, are selected from the group consisting of hydrogen, halogen, N.sub.3, OH, CN, NO.sub.2, —SCN, —SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated, C(O)—OR.sup.a, NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, O—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, NH—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c and S(═O).sub.mR.sup.e; R.sup.3, R.sup.6 independently of each other, are selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated, C(O)—OR.sup.a, NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, O—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, NH—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c, S(═O).sub.mR.sup.e, phenyl and benzyl, wherein the phenyl ring in the last 2 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; R.sup.4, R.sup.5 independently of each other, are selected from the group consisting of hydrogen, halogen, CN, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio and C.sub.1-C.sub.4-haloalkylthio or C(R.sup.4,R.sup.5) is a carbonyl group or thiocarbonyl group; R.sup.8, R.sup.9 independently of each other, are selected from the group consisting of hydrogen, halogen, CN, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio and C.sub.1-C.sub.4-haloalkylthio or C(R.sup.8,R.sup.9) is a carbonyl group or thiocarbonyl group; Ar is phenyl or 5- or 6-membered hetaryl, which are unsubstituted or carry 1, 2, 3 or 4 radicals R.sup.Ar, which are identical or different, wherein R.sup.Ar independently of each other, are selected from the group consisting of halogen, N.sub.3, OH, CN, NO.sub.2, —SCN, —SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated, C(O)—OR.sup.a, NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, O—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, NH—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c and S(═O).sub.mR.sup.e, one radical may also be phenyl, phenoxy, phenylcarbonyl, phenylthio or benzyl, wherein the phenyl ring in the last 5 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; Q is —O—, —S—, —S(═O)—, —S(═O).sub.2—, —C(R.sup.Q2aR.sup.Q2b)—, —N(R.sup.Q1)—, —N(R.sup.Q2)—C(═O)—, —N(R.sup.Q2)—C(═S)—, —O—C(═O)—, —C(R.sup.Q3)═C(R.sup.Q4)—, —C(R.sup.Q3aR.sup.Q3b)—C(R.sup.Q4aR.sup.Q4b)—, —C(R.sup.Q3aR.sup.Q3b)—C(═O)—, —O—C(R.sup.Q4aR.sup.Q4b)—, —S(═O).sub.n—C(R.sup.Q4aR.sup.Q4b)—, —N═C(R.sup.Q3c), —S(═O).sub.2—N(R.sup.Q2)— or —N(R.sup.Q2)—C(R.sup.Q4aR.sup.Q4b)—, wherein n is 0, 1 or 2; R.sup.Q1, R.sup.Q2 independently of each other are selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated, C(O)—OR.sup.a, NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c, S(═O).sub.mR.sup.e, phenyl and benzyl, wherein the phenyl ring in the last 2 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; R.sup.Q3, R.sup.Q4 independently of each other, are selected from the group consisting of hydrogen, halogen, OH, CN, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C(O)—OR.sup.a, NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, O—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, NH—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c and S(═O).sub.mR.sup.e; R.sup.Q2a, R.sup.Q2b independently of each other, are selected from the group consisting of hydrogen, halogen, CN, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio and C.sub.1-C.sub.4-haloalkylthio or —C(R.sup.Q2aR.sup.Q2b)— is C═O or C═S; R.sup.Q3a, R.sup.Q3b independently of each other, are selected from the group consisting of hydrogen, halogen, CN, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio and C.sub.1-C.sub.4-haloalkylthio; R.sup.Q3c is selected from the group consisting of hydrogen, halogen, CN, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio and C.sub.1-C.sub.4-haloalkylthio; R.sup.Q4a, R.sup.Q4b independently of each other, are selected from the group consisting of hydrogen, halogen, CN, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio and C.sub.1-C.sub.4-haloalkylthio; R.sup.1 is a moiety of the formula -T-X.sup.1—Y—Z.sup.1—R.sup.11 or a moiety -T-X.sup.2—Y—Z.sup.2—R.sup.12, wherein R.sup.11 is selected from the group consisting of C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, aryl, arylcarbonyl, aryl-C.sub.1-C.sub.4-alkyl, aryloxy-C.sub.1-C.sub.4-alkyl, hetaryl, hetarylcarbonyl, hetaryl-C.sub.1-C.sub.4-alkyl and hetaryloxy-C.sub.1-C.sub.4-alkyl, wherein the aryl and hetaryl rings in the last 8 radicals are unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.g and wherein hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9- or 10-membered bicyclic hetaryl; R.sup.12 is a radical of the formula A; ##STR00080## wherein # indicates the point of attachment to Z.sup.2; R.sup.121, R.sup.122, R.sup.123 independently of each other are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-alkynyloxy, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.6-alkylcarbonlyoxy, C.sub.1-C.sub.6-haloalkylcarbonlyoxy, C.sub.1-C.sub.6-alkenylcarbonlyoxy, C.sub.3-C.sub.6-cycloalkylcarbonlyoxy and NR.sup.bR.sup.c, or one of R.sup.121, R.sup.122, R.sup.123 also is oxo; R.sup.124 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy and C.sub.2-C.sub.6-alkenyloxy; T is selected from a single bond, (CHR.sup.xa).sub.s with s being 1, 2, 3 or 4, cyclopropane-1,1-diyl or cyclopropane-1,2-diyl, X.sup.1, X.sup.2 independently of each other, are selected from NR.sup.x1, a bivalent group —N(R.sup.x2)—C(═O)—, wherein C═(O) is bound to Y, a bivalent group —N(R.sup.x2)—C(═S)—, wherein C═(S) is bound to Y, and a bivalent group —C(R.sup.x3)═N—, wherein the nitrogen is bound to Y, Y is a single bond, or one of the bivalent groups —N(R.sup.y1)—C(═O)—, —N(R.sup.y2)—C(═S)—, —N═C((O).sub.p—R.sup.y3)— or —N═C((S).sub.p—R.sup.y3)—, wherein the left hand nitrogen atom in the four groups is bound to X.sup.1 or X.sup.2, respectively, and wherein p is 0 or 1, provided that Y is not a single bond, if X.sup.1 or X.sup.2 are a single bond; Z.sup.1 is O, S, N—R.sup.z1, C(R.sup.z3)═C((S).sub.q—R.sup.z4)—N(R.sup.z5), wherein R.sup.11 is bound to the nitrogen atom and q is 0 or 1, or C(S—R.sup.Z6)═N, wherein R.sup.11 is bound to the nitrogen atom; or Y—Z.sup.1 is selected from the following bivalent radicals N(R.sup.y4)—C(S—R.sup.Z6)═N, O—N(R.sup.y4)—C(S—R.sup.Z6)═N and N(R.sup.y44)—N(R.sup.y4)—C(S—R.sup.Z6)═N, wherein in these bivalent radicals R.sup.11 is bound to the nitrogen atom, Z.sup.2 is O, S or N—R.sup.z2; and wherein R.sup.x1, R.sup.x2 independently of each other, are selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, C(O)—OR.sup.a, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c, S(═O).sub.mR.sup.e, phenyl and benzyl, wherein the phenyl ring in the last 2 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; R.sup.x3 is selected from the group consisting of hydrogen, halogen, CN, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, O—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, NH—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, phenyl, phenoxy, phenylcarbonyl, phenylthio and benzyl, wherein the phenyl ring in the last 5 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; R.sup.xa is selected from the group consisting of hydrogen, halogen and C.sub.1-C.sub.6-alkyl, it being possible for s=2, 3 or 4 that R.sup.xa is identical or different; p is 0 or 1; R.sup.y1, R.sup.y2 independently of each other, are selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 4 mentioned radicals are unsubstituted or partially or completely halogenated, C(O)—OR.sup.a, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c, S(═O).sub.mR.sup.e, phenyl and benzyl, wherein the phenyl ring in the last 2 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; R.sup.y3 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, phenyl, phenylcarbonyl and benzyl, wherein the phenyl ring in the last 3 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; R.sup.y4 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 4 mentioned radicals are unsubstituted or partially or completely halogenated, C(O)—OR.sup.a, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c, S(═O).sub.mR.sup.e, phenyl and benzyl, wherein the phenyl ring in the last 2 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; R.sup.y44 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, phenyl, phenylcarbonyl and benzyl, wherein the phenyl ring in the last 3 radicals is unsubstituted or carries 1, 2, 3, 4 or 5 radicals R.sup.f; R.sup.z1, R.sup.z2 independently of each other are selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 4 mentioned radicals are unsubstituted or partially or completely halogenated, C(O)—OR.sup.a, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c, S(═O).sub.mR.sup.e, phenyl and benzyl, wherein the phenyl ring in the last 2 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; R.sup.z3, R.sup.z6 independently of each other, are selected from the group consisting of hydrogen, CN, halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, phenyl and benzyl, wherein the phenyl ring in the last 2 radicals is unsubstituted or carries 1, 2, 3, 4 or 5 radicals R.sup.f; R.sup.z4, R.sup.z5 independently of each other, are selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, phenyl and benzyl, wherein the phenyl ring in the last 2 radicals is unsubstituted or carries 1, 2, 3, 4 or 5 radicals R.sup.f; R is selected from the group consisting of hydrogen, halogen, N.sub.3, OH, CN, NO.sub.2, —SCN, —SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxyx-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated, C(O)—OR.sup.a, NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, O—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, NH—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c and S(═O).sub.mR.sup.e, one radical is also phenyl, phenoxy, phenylcarbonyl, phenylthio or benzyl, wherein the phenyl ring in the last 5 radicals is unsubstituted or carries 1, 2, 3, 4 or 5 radicals R.sup.f, and any combination thereof; R′ is selected from the group consisting of hydrogen, halogen, CN, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, O—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, NH—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, phenyl, phenoxy, phenylcarbonyl, phenylthio and benzyl, wherein the phenyl ring in the last 5 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; and wherein each m is independently 0, 1 or 2; each R.sup.a is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 4 mentioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, phenyl and benzyl, wherein the phenyl ring in the last 2 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; each R.sup.b is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 4 mentioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.6-alkylen-CN, phenyl and benzyl, wherein the phenyl ring in the last 2 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; each R.sup.c is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 4 mentioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.6-alkylen-CN, phenyl and benzyl, wherein the phenyl ring in the last 2 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; each moiety NR.sup.bR.sup.c forms an N-bound, saturated 5- to 8-membered heterocycle, which in addition to the nitrogen atom has 1 or 2 further heteroatoms or heteroatom moieties selected from O, S(═O).sub.m and N—R′, wherein R′ is hydrogen or C.sub.1-C.sub.6-alkyl and wherein the N-bound heterocycle is unsubstituted or carries 1, 2, 3, 4, 5 or 6 radicals selected from halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy, and any combination thereof; each R.sup.d is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 4 mentioned radicals are unsubstituted or partially or completely halogenated, phenyl and benzyl, wherein the phenyl ring in the last 2 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; each R.sup.e is selected from the group consisting of C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, wherein the alkyl and cycloalkyl parts of the last 2 mentioned radicals are unsubstituted or partially or completely halogenated, phenyl and benzyl, wherein the phenyl ring in the last 2 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; each R.sup.f is selected from the group consisting of halogen, N.sub.3, OH, CN, NO.sub.2, —SCN, —SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxyx-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated, C(O)—OR.sup.a, NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, O—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, NH—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c and S(═O).sub.mR.sup.e; each R.sup.g is selected from the group consisting of halogen, N.sub.3, OH, CN, NO.sub.2, —SCN, —SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated, C(O)—OR.sup.a, NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, O—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, NH—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C(O)—NR.sup.bR.sup.c, C(O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c and S(═O).sub.mR.sup.e; each R.sup.hh is selected from halogen, OH, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, and CN; and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

    2. The compounds of claim 1, further comprising a compound of the formulae Ia, Ib, Ic or Id, an N-oxide, stereoisomer, tautomer or agriculturally or veterinarily acceptable salt thereof: ##STR00081## wherein in formula Ia A.sup.2a is N or C(R.sup.2); and A.sup.3a is N or C(R.sup.7); wherein in formula Ib C.sup.1 is CH or C, provided that custom-character indicates a single bond, if C.sup.1 is CH or a double bond, if C.sup.1 is C, A.sup.2b is N(R.sup.3), O or S; and A.sup.3b is N or C(R.sup.7); provided that one or both of A.sup.2b and A.sup.3b are N or N(R.sup.3), respectively; wherein in formula Ic C.sup.1 and C.sup.2 are both CH or both C provided that custom-character indicates a single bond, if C.sup.1 and C.sup.2 are CH or a double bond, if C.sup.1 and C.sup.2 are C, A.sup.2c is N or C(R.sup.2); and A.sup.3c is O, S, N(R.sup.6) or C(R.sup.8,R.sup.9); wherein in formula Id A.sup.2d is N(R.sup.3), O, S or C(R.sup.4,R.sup.5); and A.sup.3d is O, S, N(R.sup.6) or C(R.sup.8,R.sup.9); provided that at least one of A.sup.2d and A.sup.3d is different from O and S and further provided that the bond between A.sup.2d and A.sup.3d is a single bond; wherein k is 0 or 1; and wherein A.sup.4, A.sup.5, A.sup.6, Ar, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are as defined in claim 1.

    3. The compound of claim 2, selected from compounds of the formulae (I), (Ia), (Ib), (Ic) and (Id), wherein A.sup.4 is N, while A.sup.5 is CH and A.sup.6 is CH; or A.sup.5 is N, while A.sup.4 is CH and A.sup.6 is CH; or A.sup.6 is N, while A.sup.4 is CH and A.sup.5 is CH; or A.sup.4 is N, A.sup.5 is N and A.sup.6 is CH; or A.sup.4 is N, A.sup.6 is N and A.sup.5 is CH; or A.sup.5 is N, A.sup.6 is N and A.sup.4 is CH.

    4. The compound of claim 1, wherein Q is selected from the group consisting of O, S, —CH.sub.2—, —N(R.sup.Q1)—, —CH═CH—, —CH.sub.2CH.sub.2—, —N═CH—, O—CH.sub.2, —S—CH.sub.2, —S(═O)—CH.sub.2—, —S(═O).sub.2—CH.sub.2—, —N(R.sup.Q2)—C(═O)—, —N(R.sup.Q2)—C(═S)—, —N(R.sup.Q2)—S(═O).sub.2—, and —N(R.sup.Q2)—CH.sub.2—, wherein R.sup.Q1 and R.sup.Q2 are as defined in claim 1.

    5. The compound of claim 1, wherein Ar is phenyl, pyridyl, pyrimidinyl or pyridazinyl, which are unsubstituted or carry 1, 2 or 3 radicals R.sup.Ar.

    6. The compound of claim 1, wherein R.sup.Ar is selected from the group consisting of halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy and S—R.sup.e, wherein R.sup.e is C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-haloalkyl.

    7. The compound of claim 1, wherein R.sup.1 is a moiety -T-X.sup.1—Y—Z.sup.1—R.sup.11.

    8. The compound of claim 1, wherein R.sup.11 is aryl, aryl-C.sub.1-C.sub.4-alkyl, hetaryl, or hetaryl-C.sub.1-C.sub.4-alkyl, wherein the aryl and hetaryl rings in the last 4 radicals are unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.g and wherein hetaryl is a 5- or 6-membered monocyclic hetaryl.

    9. The compound of claim 1, wherein R.sup.1 is a moiety -T-X.sup.2—Y—Z.sup.2—R.sup.12, wherein T is a single bond, CH.sub.2, CH.sub.2CH.sub.2 or cyclopropan-1,2-diyl; X.sup.2 is CH═N or NHC(O); Y is a single bond; Z.sup.2 is O; and R.sup.12 is a radical of the formula A, wherein R.sup.121 is C.sub.1-C.sub.4-alkoxy; R.sup.122 is C.sub.1-C.sub.4-alkoxy or C.sub.3-C.sub.4-alkenyloxy; R.sup.123 is OH, C.sub.1-C.sub.4-alkoxy or C.sub.3-C.sub.4-alkenyloxy; and R.sup.124 is C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl.

    10. The compound of claim 1, which is selected from the group consisting of compounds: 1-(2,6-dimethylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2-isopropylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]thiourea, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2-isopropyl-5-methyl-phenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]thiourea, (2Z)-3-(2-isopropyl-5-methyl-phenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one, (2Z)-2-(2,6-dimethylphenyl)imino-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]thiazolidin-4-one, (2Z)-2-(2-isopropylphenyl)imino-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]thiazolidin-4-one, 1-(2,6-dimethylphenyl)-3-[(E)-[3-[6-(trifluoromethyl)pyridazin-3-yl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[3-[6-(trifluoromethyl)pyridazin-3-yl]imidazo[4,5-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2,6-dimethylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]-4,5-dihydroimidazo[4,5-f]quinolin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]-4,5-dihydroimidazo[4,5-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2,6-dimethylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]-4,5-dihydroimidazo[4,5-f]quinazolin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]-4,5-dihydroimidazo[4,5-f]quinazolin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2,6-dimethylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinazolin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinazolin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2,6-dimethylphenyl)-3-[(E)-[5,5-dioxo-3-[4-(trifluoromethoxy)phenyl]-4H-imidazo[2,3]thiopyrano[2,4-b]pyridin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[5,5-dioxo-3-[4-(trifluoromethoxy)phenyl]-4H-imidazo[2,3]thiopyrano[2,4-b]pyridin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2,6-dimethylphenyl)-3-[(E)-[5,5-dioxo-3-[4-(trifluoromethoxy)phenyl]-4H-imidazo[2,3]thiopyrano[2,4-d]pyrimidin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[5,5-dioxo-3-[4-(trifluoromethoxy)phenyl]-4H-imidazo[2,3]thiopyrano[2,4-d]pyrimidin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2,6-dimethylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoxalin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoxalin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2,6-dimethylphenyl)-3-[(E)-[2-methyl-3-[4-(trifluoromethoxy)phenyl]-4,5-dihydropyrazolo[3,4-f]quinolin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[2-methyl-3-[4-(trifluoromethoxy)phenyl]-4,5-dihydropyrazolo[3,4-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2,6-dimethylphenyl)-3-[(E)-[2-methyl-3-[4-(trifluoromethoxy)phenyl]-4,5-dihydropyrazolo[3,4-f]quinazolin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[2-methyl-3-[4-(trifluoromethoxy)phenyl]-4,5-dihydropyrazolo[3,4-f]quinazol in-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2,6-dimethylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoxalin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoxalin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2,6-dimethylphenyl)-3-[(E)-[2-methyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-f]quinolin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[2-methyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2,6-dimethylphenyl)-3-[(E)-[2-methyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-f]quinazolin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[2-methyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-f]quinazolin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2,6-dimethylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2,6-dimethylphenyl)-3-[(E)-[2-methyl-5,5-dioxo-3-[4-(trifluoromethoxy)phenyl]-4H-pyrazolo[1,2]thiopyrano[3,4-b]pyridin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[2-methyl-5,5-dioxo-3-[4-(trifluoromethoxy)phenyl]-4H-pyrazolo[1,2]thiopyrano[3,4-b]pyridin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2,6-dimethylphenyl)-3-[(E)-[2-methyl-5,5-dioxo-3-[4-(trifluoromethoxy)phenyl]-4H-pyrazolo[1,2]thiopyrano[3,4-d]pyrimidin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[2-methyl-5,5-dioxo-3-[4-(trifluoromethoxy)phenyl]-4H-pyrazolo[1,2]thiopyrano[3,4-d]pyrimidin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2,6-dimethylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]quinolin-7-yl]methyleneamino]thiourea, (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one, (2Z)-3-(2-isopropylphenyl)-4-methyl-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-ol, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[3-[6-(trifluoromethyl)pyridazin-3-yl]imidazo[4,5-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(5-chloro-2-pyridyl)ethyl N-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]carbamate, (2-isopropyl-5-methylcyclohexyl)N-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]carbamate, 1-(2-isopropylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]quinolin-7-yl]methyleneamino]thiourea, (2Z)-2-(2-isopropylphenyl)imino-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]quinolin-7-yl]methyleneamino]thiazolidin-4-one, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one, (2Z)-2-(2,6-dimethylphenyl)imino-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]quinolin-7-yl]methyleneamino]thiazolidin-4-one, 1-(2-isopropylphenyl)-3-[(E)-[2-methyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-f]quinolin-7-yl]methyleneamino]thiourea, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[2-methyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one, (E)-3-(2-isopropylphenyl)-N-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]thiazolidin-2-imine, (E)-3-(2-isopropylphenyl)-N-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]-1,3-thiazinan-2-imine, (E)-3-(2,6-dimethylphenyl)-N-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]-1,3-thiazinan-2-imine, 1-(2-isopropylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin-7-yl]methyleneamino]thiourea, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin-7-yl]methylenehydrazono]thiazolidin-4-one, (2Z)-2-(2-isopropylphenyl)imino-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin-7-yl]methyleneamino]thiazolidin-4-one, 2Z)-2-(2,6-dimethylphenyl)imino-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin-7-yl]methyleneamino]thiazolidin-4-one, (E)-3-(2,6-dimethylphenyl)-N-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]thiazolidin-2-imine, 1-[(E)-[3-[4-(difluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]-3-(2-isopropylphenyl)thiourea, (2E)-2-[(E)-[3-[4-(difluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methylenehydrazono]-3-(2-isopropylphenyl)thiazolidin-4-one, (E)-1-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]-N-[(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]oxy-methanimine, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoxalin-7-yl]methylenehydrazono]thiazolidin-4-one, 1-(2-isopropylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoxalin-7-yl]methyleneamino]thiourea, 1-(2-isopropylphenyl)-3-[(E)-[2-methyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-f]quinazolin-7-yl]methyleneamino]thiourea, and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

    11. Compounds of the formula (INT): ##STR00082## wherein R.sup.1a is -T-NCO, -T-C(═O)R.sup.x3a, -T-C(═O)—N.sub.3, T-CN, -T-N(R.sup.y1a)H or halogen and wherein T is selected from a single bond, (CHR.sup.xa).sub.s with s being 1, 2, 3 or 4, cyclopropane-1,1-diyl or cyclopropane-1,2-diyl, R.sup.y1a is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, phenyl and benzyl, wherein the phenyl ring in the last 2 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; R.sup.x3a is selected from the group consisting of hydrogen, OH, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, wherein the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated, C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, O—C.sub.1-C.sub.6-alkylen-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylen-CN, phenyl, phenoxy, phenylcarbonyl, phenylthio and benzyl, wherein the phenyl ring in the last 5 radicals is unsubstituted or carry 1, 2, 3, 4 or 5 radicals R.sup.f; and wherein Ar, R.sup.xa, A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5, A.sup.6, C.sup.1, C.sup.2 and Q are as defined in any of the preceding claims and the salts thereof.

    12. A composition comprising at least one compound of the formula I, as defined in claim 1, any stereoisomer thereof or any agriculturally or veterinarily acceptable salt thereof, and at least one agriculturally or veterinarily acceptable carrier selected from the group consisting of an inert liquid, and a solid.

    13. (canceled)

    14. (canceled)

    15. A method for controlling invertebrate pests, the method comprising treating the pests, their food supply, their habitat or their breeding ground or a plant, plant propagation material, soil, area, material or environment in which the pests are growing or may grow, or the materials, plants, plant propagation material, soils, surfaces or spaces to be protected from invertebrate pest attack or infestation with a pesticidally effective amount of at least one imine compound of the formula I as defined in claim 1, a stereoisomer thereof or an agriculturally acceptable salt thereof.

    16. A plant propagation material, comprising at least one compound of the formula I as defined in claim 1, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.

    17. A method for treating or protecting an animal from infestation or infection by invertebrate pests, the method comprising bringing the animal in contact with a pesticidally effective amount of at least one compound of the formula I as defined in claim 1, a stereoisomer thereof or at least one veterinarily acceptable salt thereof.

    18. The compound of claim 1, wherein R.sup.z1 together with R.sup.y3, if present, form a linear C.sub.1-C.sub.6-alkylene group or a linear C.sub.2-C.sub.6-alkenylene group, wherein, in the linear C.sub.1-C.sub.6-alkylene group and the linear C.sub.2-C.sub.6-alkenylene group: a CH.sub.2 moiety is retained or is replaced by a carbonyl group or a group C═N—R′; 1 or 2 CH.sub.2 moieties are retained or replaced by O or S; the linear C.sub.1-C.sub.6-alkylene group and the linear C.sub.2-C.sub.6-alkenylene group is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 radicals R.sup.hh as defined in claim 1; and any combination thereof.

    19. The compound of claim 1, wherein R.sup.z4 together with R.sup.z5, if present, form a linear C.sub.1-C.sub.6-alkylene group or a linear C.sub.2-C.sub.6-alkenylene group, wherein in the linear C.sub.1-C.sub.6-alkylene group and the linear C.sub.2-C.sub.6-alkenylene group: a CH.sub.2 moiety is replaced by a carbonyl group or a group C═N—R′; 1 or 2 CH.sub.2 moieties are replaced by O or S; the linear C.sub.1-C.sub.6-alkylene group and the linear C.sub.2-C.sub.6-alkenylene group are unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 radicals R.sup.hh; and any combination thereof.

    20. The compound of claim 1, wherein R.sup.y4 together with R.sup.z6, if present, form a linear C.sub.1-C.sub.6-alkylene group or a linear C.sub.2-C.sub.6-alkenylene group, wherein in the linear C.sub.1-C.sub.6-alkylene group and the linear C.sub.2-C.sub.6-alkenylene group: a CH.sub.2 moiety is be replaced by a carbonyl group or a group C═N—R′; 1 or 2 CH.sub.2 moieties are replaced by O or S; the linear C.sub.1-C.sub.6-alkylene group and the linear C.sub.1-C.sub.6-alkenylene group are unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 radicals R.sup.hh; and any combination thereof.

    Description

    EXAMPLES

    [0949] The present invention is now illustrated in further details by the following examples.

    [0950] Compounds can be characterized e.g. by coupled High Performance Liquid Chromatography/mass spectrometry (HPLC/MS), by .sup.1H-NMR and/or by their melting points.

    [0951] Analytical HPLC:

    [0952] Method 1: Phenomenex Kinetex 1.7 μm XB-C18 100A; 50×2.1 mm. Elution: acetonitrile+0.1% trifluoroacetic acid (TFA)/water+0.1% trifluoroacetic acid (TFA) in a ratio of from 5:95 to 95:5 in 1.5 minutes at 50° C.

    [0953] Method 2: BEH C18 1.7 μm; 50×2.1 mm. Elution: acetonitrile+0.1% formic acid (FA)/water+0.1% 0.1% formic acid (FA) in a ratio of from 5:95 to 95:5 in 5 minutes at 40° C.

    [0954] Method 3: Agilent Eclipse Plus C18, 50×4.6 mm, ID 5 μm; Elution: A=10 mM Amm. Formate (0.1% Formic Acid), B=Acetonitrile (0.1% Formic Acid), Flow=1.2 ml/min. at 30° C.; Gradient:=10% B to 100% B-3 min, hold for 1 min, 1 min-10% B. Run Time=5.01 min.

    [0955] .sup.1H-NMR: The signals are characterized by chemical shift (ppm, δ [delta]) vs. tetramethylsilane, respectively CDCl.sub.3 for .sup.13C-NMR, by their multiplicity and by their integral (relative number of hydrogen atoms given). The following abbreviations are used to characterize the multiplicity of the signals: m=multiplet, q=quartet, t=triplet, d=doublet and s=singlet.

    [0956] Abbreviations used are: d for day(s), h for hour(s), min for minute(s), r.t./room temperature for 20-25° C., Rt for retention time; DMSO for dimethyl sulfoxide, OAc for acetate, EtOAc for ethyl acetate, THF for tetrahydrofuran, and t-BuOH for tert-butanol.

    Synthesis Examples

    Example 1: 3-(2,6-dimethylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one (Compound C-2)

    Step 1: 6-Fluoro-2-methyl-5-nitro-quinoline

    [0957] To a solution of 6-fluoro 2-methylquinoline (5 g, 31 mmol) in concentrated sulfuric acid (30 mL) at 0° C. was added sodium nitrite (2.9 g, 34.12 mmol). The reaction mixture was stirred at room temperature for 12 h and subsequently poured into a mixture of ice and water. The mixture was basified with saturated sodium bicarbonate solution. The suspended solids were filtered and dried and purified by silica gel flash column chromatography eluting with 15% ethyl acetate in heptane to afford the title compound (3.5 g, 54% yield) as a yellow solid. LC/MS (method 3): R.sub.t: 2.45 min; MS: m/z=207 (M)+; .sup.1H NMR (300 MHz, DMSO-d.sub.6): δ 8.34-8.29 (m, 2H), 7.96 (m, 1H), 7.71 (d, J=6 Hz, 1H), 2.70 (s, 3H).

    Step 2: 2-Methyl-5-nitro-N-[4-(trifluoromethoxy)phenyl]quinolin-6-amine

    [0958] A mixture of 6-fluoro-2-methyl-5-nitro-quinoline (2.2 g, 10.7 mmol) and 4-trifluoromethoxy aniline (3.78 g, 21.34 mmol) in acetonitrile was heated at 80° C. for 24 h. The reaction was allowed to cool to ambient temperature and was evaporated under vacuum. Water (100 mL) was added to the residue and the mixture was extracted with ethyl acetate (2×100 mL). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated under vacuum to get a residue which was purified by silica gel flash column chromatography eluting with 12% ethyl acetate in heptane to afford the title product (3.5 g, 90% yield) as a yellow solid. LC/MS (method 3): R.sub.t: 3.24 min; MS: m/z=364 (M.sup.+); .sup.1H NMR (300 MHz, DMSO-d.sub.6): δ 9.75 (s, 1H), 8.91 (d, J=9 Hz, 1H), 8.04 (s, 1H), 7.54-7.44 (m, 2H), 7.39 (m, 4H), 2.74 (s, 3H).

    Step 3: 2-Methyl-N6-[4-(trifluoromethoxy)phenyl]quinoline-5,6-diamine

    [0959] To a solution of 2-methyl-5-nitro-N-[4-(trifluoromethoxy)phenyl]quinolin-6-amine (3.5 g, 9.63 mmol) in methanol (50 mL) was added stannous chloride (6.5 g, 28.9 mmol) and maintained at 60° C. for 4 h. The reaction was cooled to ambient temperature and water (100 mL) was added and the mixture basified with saturated sodium bicarbonate solution. Ethyl acetate (200 mL) was added and the mixture was filtered through a celite bed. The organic part of the filtrate was separated and dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue obtained was triturated with pentane to get the title compound (3 g, 93% yield) as an off white solid. LC/MS (method 3): R.sub.t: 2.05 min; MS: m/z=334 (M.sup.+); .sup.1H NMR (300 MHz, DMSO-d.sub.6): δ 8.47 (d, J=6 Hz, 1H), 7.58 (s, 1H), 7.37 (d, J=9 Hz, 1H), 7.28 (d, J=9 Hz, 1H), 7.19 (d, J=9 Hz, 1H), 7.12-7.17 (m, 2H), 6.47-6.67 (m, 2H), 5.54 (s, 2H), 2.59 (s, 3H).

    Step 4: 7-Methyl-3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolone

    [0960] 2-Methyl-N6-[4-(trifluoromethoxy)phenyl]quinoline-5,6-diamine (3 g, 9 mmol) was taken up in formic acid (50 mL) and maintained at 50° C. for 5 h. The reaction was cooled to ambient temperature and the volatiles were evaporated under vacuum. The residue obtained was suspended in water (100 mL) and basified with saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate (2×100 mL). The combined ethyl acetate extracts were dried over anhydrous sodium sulfate and concentrated under vacuum to get the title product as a beige solid (2.8 g, 90% yield). LC/MS (method 3): R.sub.t: 2.18 min; MS: m/z=344 (M.sup.+); .sup.1H NMR (300 MHz, DMSO-d.sub.6): δ 8.79 (d, J=9 Hz, 1H), 8.72 (s, 1H), 7.96-7.91 (m, 3H), 7.84 (d, J=9 Hz, 1H), 7.67-7.70 (m, 2H), 7.58 (d, J=9 Hz, 1H), 2.70 (s, 3H).

    Step 5: 3-[4-(Trifluoromethoxy)phenyl]imidazo[4,5-f]quinoline-7-carbaldehyde

    [0961] To a suspension of selenium dioxide (5.43 g, 48.94 mmol) in 1,4-dioxane (80 mL) at 60° C. 7-methyl-3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolone was added in one portion. The reaction mixture was heated at 80° C. for 12 h and subsequently cooled to ambient temperature. Water (100 mL) was added and the mixture was extracted with Ethyl acetate (2×100 mL). The combined organic extracts were passed through a celite bed and dried over anhydrous sodium sulphate and concentrated under vacuum. The residue obtained was purified by silica gel flash column chromatography eluting with 50% ethyl acetate in heptane to afford the title compound (2.6 g, 89% yield) as an off white solid. LC/MS (method 3): R.sub.t: 2.86 min; MS: m/z=358 (M.sup.+); .sup.1H NMR (300 MHz, DMSO-d.sub.6): δ 10.17 (s, 1H), 9.11 (d, J=9 Hz, 1H), 8.85 (m, 1H), 8.17 (d, J=9 Hz, 1H), 8.143-8.146 (m, 2H), 7.95-7.98 (m, 2H), 7.72 (d, J=9 Hz, 2H).

    Step 6: 1-(2,6-Dimethylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]thiourea

    [0962] A mixture of 3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoline-7-carbaldehyde (400 mg, 1.12 mmol) and 1-amino-3-(2,6-dimethylphenyl)thiourea (220 mg, 1.12 mmol) in ethanol (30 mL) was heated at 80° C. for 5 h. The reaction mixture was allowed to cool to ambient temperature and the precipitated solid was collected by filtration and washed with cold ethanol and dried under vacuum to afford 500 mg (83% yield) of title compound as a beige solid. LC/MS (method 3): R.sub.t: 3.10 min; MS: m/z=535 (M)+); .sup.1H NMR (300 MHz, DMSO-d.sub.6): δ 12.11 (s, 1H), 10.18 (s, 1H), 8.85-8.76 (m, 3H), 8.35 (s, 1H), 8.02-7.95 (m, 4H), 7.69-7.66 (m, 2H), 7.15-7.14 (m, 3H), 2.21 (s, 6H).

    Step 7: 3-(2,6-dimethylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one

    [0963] To a solution of 1-(2,6-dimethylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]thiourea (200 mg, 0.37 mmol) and sodium acetate (90 mg, 1.12 mmol) in ethanol (20 mL) was added methyl bromoacetate (0.05 mL, 0.56 mmol) and reaction mixture was stirred at 65° C. for 48 h. The reaction mixture was evaporated under reduced pressure and water (50 mL) was added and extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried over anhydrous sodium sulphate concentrated under vacuum and the residue was purified by silica gel flash column chromatography eluting with 30% ethyl acetate in n-heptane as an eluent to afford 150 mg (70% yield) of the title compound as a beige solid. LC/MS (method 3): R.sub.t: 3.31 min; MS: m/z=575 (M.sup.+). .sup.1H NMR (300 MHz, DMSO-d.sub.6): δ 9.00 (d, J=9 Hz, 1H), 8.79 (s, 1H), 8.34 (s, 1H), 8.29 (d, J=9 Hz, 1H), 8.03 (d, J=9 Hz, 1H), 7.96-7.92 (m, 3H), 7.71 (d, J=9 Hz, 2H), 7.34-7.29 (m, 1H), 7.25-7.23 (m, 2H), 4.34 (s, 2H), 2.14 (s, 6H).

    Example 2: 3-(2-Isopropyl-5-methyl-phenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one (Compound C-6)

    Step 1: 1-(2-Isopropyl-5-methyl-phenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]thiourea

    [0964] A mixture of 3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoline-7-carbaldehyde (200 mg, 0.56 mmol) and 1-amino-3-(2-isopropyl-5-methyl-phenyl)thiourea (140 mg, 0.62 mmol) in 30 mL of ethanol was heated at 80° C. for 2 h. The reaction mixture was allowed to cool to ambient temperature and the solid precipitated was filtered, washed with cold ethanol and dried to afford 210 mg (65% yield) of the title compound as a beige solid. LC/MS (method 3): R.sub.t: 3.34 min; MS: m/z=563 (M.sup.+); .sup.1H NMR (300 MHz, DMSO-d.sub.6): δ 12.11 (s, 1H), 10.25 (s, 1H), 8.87 (d, J=9 Hz, 1H), 8.78-8.75 (m, 2H), 8.37 (s, 1H), 8.03 (d, J=9.3 Hz, 1H), 7.93-7.97 (m, 3H), 7.71 (d, J=9 Hz, 2H), 7.28 (d, J=9 Hz, 1H), 7.15 (d, J=6 Hz, 1H), 7.02 (s, 1H), 3.17 (m, 1H), 2.31 (s, 3H), 1.22 (d, J=6 Hz, 6H).

    Step 2: 3-(2-Isopropyl-5-methyl-phenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one

    [0965] To a solution of 1-(2-isopropyl-5-methylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]thiourea (160 mg, 0.28 mmol) and sodium acetate (70 mg, 0.85 mmol) in Ethanol (20 mL) was added Methyl bromoacetate (90 mg, 0.57 mmol) and the mixture was stirred at 45° C. for 24 h. The volatiles were evaporated under vacuum and water (50 mL) was added and the mixture extracted with ethylacetate (2×15 mL). The combined organic extracts were dried over anhydrous sodium sulfate and were concentrated under vacuum to get a residue which was purified by silica gel flash column chromatography eluting with 0.5% methanol in chloroform to afford 80 mg (47% yield) of the title compound as a beige solid. LC/MS (method 3): R.sub.t: 3.56 min; MS: m/z=603 (M.sup.+). .sup.1H NMR (300 MHz, DMSO-d.sub.6): δ 9.00 (d, J=9 Hz, 1H), 8.79 (s, 1H), 8.33 (s, 1H), 8.29 (d, J=14 Hz, 1H), 8.0 (d, J=15 Hz, 1H), 7.95-7.96 (m, 3H), 7.65-7.75 (m, 2H), 7.40 (d, J=9 Hz, 1H), 7.40 (d, J=9 Hz, 1H) 7.11 (s, 1H), 4.28 (m, 2H), 2.70-2.80 (m, 1H), 2.33 (s, 3H), 1.10-1.17 (m, 6H)

    Example 3: 2-(2,6-Dimethylphenyl)imino-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]thiazolidin-4-one (compound C-7)

    Step 1: 3-Amino-2-(2,6-dimethylphenyl)imino-thiazolidin-4-one

    [0966] To a solution of 1-amino-3-(2,6-dimethylphenyl)thiourea (200 mg, 1.02 mmol) and sodium acetate (170 mg, 2.05 mmol) in ethanol (20 mL) was added methyl bromoacetate (0.17 mL, 2.05 mmol) and the mixture stirred at 80° C. for 2 h. The reaction was evaporated under reduced pressure and water (20 mL) was added and the mixture was extracted with ethyl acetate (2×20 mL). The combined organic extract was dried over anhydrous sodium sulfate and concentrated under vacuum to yield the desired product as a white solid. LC/MS (method 3): R.sub.t: 2.1 min; MS: m/z=236 (M.sup.+). .sup.1H NMR (300 MHz, DMSO-d.sub.6): δ 7.05-7.02 (m, 2H), 6.88-6.93 (m, 1H), 5.33 (s, 2H), 3.96 (s, 2H), 2.05 (s, 6H).

    Step 2: 2-(2,6-Dimethylphenyl)imino-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]thiazolidin-4-one

    [0967] To a solution of 3-[4-(trifluoromethoxy)phenyl]benzo[e]benzimidazole-7-carbaldehyde (120 mg, 0.34 mmol) in acetic acid (10 mL) was added 3-amino-2-(2,6-dimethylphenyl)imino-thiazolidin-4-one (80 mg, 0.34 mmol) and the mixture stirred at ambient temperature for 1 h. The reaction was diluted with water (50 mL) and basified with saturated sodium bicarbonate solution and extracted with EtOAc (2×50 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum and the residue obtained was triturated with diethyl ether to afford 160 mg (83% yield) of title product as an off white solid. LC/MS (method 3): R.sub.t: 3.40 min; MS: m/z=575 (M.sup.+). .sup.1H NMR (300 MHz, DMSO-d.sub.6): δ 9.65 (s, 1H), 9.08 (d, J=6 Hz, 1H), 8.83 (s, 1H), 8.45 (d, J=9 Hz, 1H), 8.10-8.01 (m, 2H), 7.94-7.97 (m, 2H), 7.72 (d, J=9 Hz, 2H), 7.10 (d, J=6 Hz, 2H), 6.98 (m, 1H), 4.16 (s, 2H), 2.13 (s, 6H).

    Example 4: 3-(2-isopropylphenyl)-2-[(E)-[3-[6-(trifluoromethyl)pyridazin-3-yl]imidazo[4,5-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one (Compound C-10)

    Step 1: 2-methyl-5-nitro-quinolin-6-amine

    [0968] 6-fluoro-2-methyl-5-nitro-quinoline (3.7 g, 16.9 mmol) was stirred in aqueous. Ammonia (200 ml, 27%) for 12 h. Water (100 mL) was added and the mixture Ethyl acetate (2×50 mL). The organic extracts were dried over anhydrous sodium sulphate and evaporated under vacuum to get the title compound as a yellow solid (3 g, 87%). LC/MS (method 3): R.sub.t: 1.64 min MS: m/z=204 (M.sup.+). .sup.1H NMR (300 MHz, DMSO-d.sub.6) 1H NMR (300 MHz, DMSO-d6) δ 8.84 (d, J=8.9 Hz, 1H), 8.15 (s, 2H), 7.86 (d, J=9.4 Hz, 1H), 7.46 (d, J=8.9 Hz, 1H), 7.37 (d, J=9.4 Hz, 1H), 2.56 (s, 3H).

    Step 2: 2-methylquinoline-5,6-diamine

    [0969] To a solution of 2-methyl-5-nitro-quinolin-6-amine (3 g, 14.76 mmol) in Methanol (50 mL) was added Stannous chloride dihydrate (11.1 g, 59 mmol) and the mixture heated at 60° C. for 12 h. The reaction was cooled to room temperature and diluted with water (20 mL).Saturated Sodium bicarbonate solution (50 mL) was added and the mixture extracted with Ethyl Acetate. The Ethyl acetate extracts were dried over anhydrous Sodium sulphate and evaporated under vacuum to get a residue which was purified by silica gel flash column chromatography using 5% MeOH in Dichloromethane as an eluent to afford the title compound (1.8 g, 70%); LC/MS (method 3): R.sub.t: 0.56 min MS: m/z=174 (M.sup.+); .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 8.21 (d, J=8.7 Hz, 1H), 7.16-7.00 (m, 3H), 4.95 (s, 2H), 4.72 (s, 2H), 2.50 (s, 3H).

    Step 3: 7-methyl-3-[6-(trifluoromethyl)pyridazin-3-yl]imidazo[4,5-f]quinolone

    [0970] A solution of 2-methylquinoline-5,6-diamine (2 g, 12 mmol) in Formic acid (20 mL) was stirred at r.t. for 12 h. The volatiles were evaporated under reduced pressure and the residue was taken up in water (100 mL) and was basified with saturated Sodium bicarbonate solution and extracted with EtOAc. The Ethyl acetate extracts were dried over anhydrous Sodium Sulphate and concentrated in vacuum and the residue obtained was purified by trituration with Diethyl ether to obtain the title compound (1.5 g, 71%). LC/MS (method 3): R.sub.t: 0.62 min MS: m/z=184 (M.sup.+); .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 8.67 (d, J=8.4 Hz, 1H), 8.34 (s, 1H), 7.92 (d, J=9.0 Hz, 1H), 7.71 (d, J=9.0 Hz, 1H), 7.49 (d, J=8.4 Hz, 1H), 2.67 (s, 3H).

    Step 4: 7-methyl-3-[6-(trifluoromethyl)pyridazin-3-yl]imidazo[4,5-f]quinoline

    [0971] To a solution of 7-methyl-3H-imidazo[4,5-f]quinolone (0.2 g, 1.09 mmol) in N, N-Dimethyl formamide (1 mL), was added 3-chloro-6-(trifluoromethyl)pyridazine (0.2 g, 1.09 mmol), Cesium carbonate (0.89 g, 1.64 mmol), 8-Hydroxy quinolone (0.016 g, 0.11 mmol) and Copper Iodide (0.021 g, 0.11 mmol). The reaction mixture was heated at 90° C. for 2 h. The mixture was cooled to ambient temperature and water (50 mL) was added and extracted with Ethyl acetate (2×50 mL). The combined organic layer was dried over anhydrous Sodium sulphate and concentrated under vacuum and the residue was purified by silica gel flash column chromatography eluting with 2% Methanol in Dichloromethane to obtain the title compound (0.23 g, 64%). LC/MS (method 3): R.sub.t: 1.83 min; MS: m/z=330.1 (M.sup.+).

    Step 5: 3-[6-(trifluoromethyl)pyridazin-3-yl]imidazo[4,5-f]quinoline-7-carbaldehyde

    [0972] To a pre-heated suspension of Selenium dioxide (0.34 g, 3.04 mmol) in 1,4-dioxane at 60° C., was added 7-methyl-3-[6-(trifluoromethyl)pyridazin-3-yl]imidazo[4,5-f]quinolone (0.25 g, 0.76 mmol). The temperature of the mixture was raised to 90° C. and stirred for 12 h. The reaction was cooled to ambient temperature and water (50 mL) was added and the mixture extracted with Ethyl acetate (50 mL×2). The combined organic layer was dried over anhydrous Sodium sulphate and concentrated under vacuum and the residue obtained was purified by silica gel flash column chromatography using 2% Methanol in Dichloromethane as the eluent to obtain the title compound (0.23 g, 64%). LC/MS (method 3): R.sub.t: 2.47 min; MS: m/z=344 (M.sup.+); .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 9.35 (s, 1H), 9.00 (d, J=8.6 Hz, 1H), 8.85 (d, J=9.2 Hz, 1H), 8.79 (d, J=9.3 Hz, 1H), 8.72-8.61 (m, 2H), 7.61-7.48 (m, 2H).

    Step 6: 1-(2-isopropylphenyl)-3-[(E)-[3-[6-(trifluoromethyl)pyridazin-3-yl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]thiourea

    [0973] A solution of 3-[6-(trifluoromethyl)pyridazin-3-yl]imidazo[4,5-f]quinoline-7-carbaldehyde (0.1 g, 0.291 mmol) and 1-amino-3-(2-isopropylphenyl)thiourea (0.056 g, 0.269 mmol) in EtOH (10 mL) was heated at 80° C. for 12 h. The mixture was cooled to ambient temperature and the solid precipitated was collected by filtration and was washed with EtOH, dried under vacuum to get the desired product as an off white solid. (0.120 g, 77%). LC/MS (method 3): R.sub.t: 2.94 min; MS: m/z=535 (M.sup.+); .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 12.15 (s, 1H), 10.32 (s, 1H), 9.34 (s, 1H), 8.93-8.74 (m, 4H), 8.65 (d, J=9.2 Hz, 1H), 8.39 (s, 1H), 8.09 (d, J=9.2 Hz, 1H), 7.44-7.28 (m, 2H), 7.32-7.17 (m, 2H), 3.17 (p, J=6.7 Hz, 1H), 1.22 (d, J=6.9 Hz, 6H).

    Step 7: (2Z)-3-(2-isopropylphenyl)-2-[(E)-[3-[6-(trifluoromethyl)pyridazin-3-yl]imidazo[4,5-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one

    [0974] To the solution of 1-(2-isopropylphenyl)-3-[(E)-[3-[6-(trifluoromethyl)pyridazin-3-yl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]thiourea (0.1 g 0.187 mmol) in EtOH (10 mL) was added Sodium acetate (0.031 g, 0.374 mmol) and Methyl bromo acetate (0.057 g, 0.374 mmol) and the mixture was heated at 50° C. for 12 h. The mixture was cooled to ambient temperature and water (50 mL) was added and extracted with EtOAc (2×50 mL). The combined organic layer was dried over anhydrous Sodium sulphate and concentration under vacuum and the residue obtained was washed by trituration successively with Methanol and Diethyl ether to get the title compound as an off-white solid. (0.095 g, 88%) LC/MS (method 3): R.sub.t: 3.16 min; MS: m/z=575 (M.sup.+), .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 9.35 (s, 1H), 9.02 (d, J=8.6 Hz, 1H), 8.81 (dd, J=11.8, 9.3 Hz, 2H), 8.65 (d, J=9.3 Hz, 1H), 8.37-8.25 (m, 2H), 8.08 (d, J=9.3 Hz, 1H), 7.60-7.44 (m, 2H), 7.43-7.26 (m, 2H), 4.33 (d, J=17.4 Hz, 1H), 4.20 (d, J=17.4 Hz, 1H), 2.81 (p, J=6.8 Hz, 1H), 1.17 (dd, J=14.4, 6.8 Hz, 6H).

    Example 5: 1-(5-chloro-2-pyridyl)ethyl N-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]carbamate (compound C-11)

    Step 1: 3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoline-7-carboxylic acid

    [0975] To a preheated suspension of Selenium dioxide (5.17 g, 46.61 mmol) in Pyridine (30 mL) at 60° C. was added 7-methyl-3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoline (4 g, 11.65 mmol) in one lot. The temperature was raised up to 100° C. and the mixture stirred for 3 h. The volatiles were evaporated under reduced pressure and water (150 mL) was added and the mixture was acidified with solid Potassium hydrogen sulphate and the mixture extracted with EtOAc (2×150 mL). The combined organic layer was passed through Celite bed and the bed washed with Tetrahydrofuran. The combined filtrate was dried over anhydrous Sodium sulphate and concentrated in vacuum to get a residue which was triturated with Diethyl ether to yield the title compound as a brown solid (4 g, 92%). LC/MS (method 3): R.sub.t: 2.240 min; MS: m/z=374.1 (M.sup.+); .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 9.05 (d, J=8.5 Hz, 1H), 8.83 (s, 1H), 8.29 (d, J=8.5 Hz, 1H), 8.17-8.01 (m, 2H), 8.01-7.91 (m, 2H), 7.71 (d, J=8.4 Hz, 2H).

    Step 2: 1-(5-chloro-2-pyridyl)ethyl N-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]carbamate

    [0976] To a solution of 3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoline-7-carboxylic acid (0.2 g, 0.53 mmol) in Toluene (20 mL) was added a solution of Diphenylphosphorazidate (0.18 mL, 0.804 mmol) in toluene followed by Triethylamine (0.11 mL, 0.804 mmol) followed by 1-(5-chloro-2-pyridyl)ethanol (0.084 g, 0.536 mmol) and the mixture was heated to 100° C. for 1 h. The mixture was cooled to ambient temperature and saturated Sodium bicarbonate solution was added and the mixture extracted with Ethyl acetate (2×50 mL). The combined organic extracts were dried (anhydrous Sodium sulphate) and concentrated in vacuum to get a residue which was purified by silica gel flash column chromatography using 40% EtOAc in n-Heptane as the eluent to afford the title compound as an off-white solid (0.12 g, 42%). LC/MS (method 3): R.sub.t: 3.13 min; MS: m/z=528.3 (M.sup.+); (300 MHz, DMSO-d.sub.6) δ 10.66 (s, 1H), 8.84 (d, J=9.0 Hz, 1H), 8.70 (s, 1H), 8.62 (d, J=2.5 Hz, 1H), 8.15 (d, J=9.0 Hz, 1H), 8.00 (dd, J=8.4, 2.5 Hz, 1H), 7.92 (dd, J=9.0, 6.8 Hz, 3H), 7.69 (t, J=8.4 Hz, 3H), 7.61 (d, J=8.5 Hz, 1H), 5.84 (q, J=6.6 Hz, 1H), 1.58 (d, J=6.7 Hz, 3H).

    Example 6: 1-(2-isopropylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]quinolin-7-yl]methyleneamino]thiourea (compound C-13)

    Step 1: 3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]quinoline-7-carbaldehyde

    [0977] A mixture of 1-[4-(trifluoromethoxy)phenyl]benzimidazol-4-amine (1.5 g, 5.1 mmol) and 2-iminoethylvinamidinium tritetrafluoborate (5.46 g, 5.3 mmol) was taken up in 2-propanol (100 mL) and the mixture stirred under reflux for 16 h. The reaction mixture was allowed to cool to room temperature and 1M HCl (14 mL) was added. The mixture was stirred at 70° C. for a further 6 h. The mixture was allowed to cool to room temperature and left as such for 14 h. The precipitated solid was filtered, washed with cold 2-propanol and dried to afford 0.9 g (86%) of the title compound. LC/MS (method 3): R.sub.t: 2.55 min; MS: m/z=358 (M.sup.+), .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ10.29 (s, 1H), 9.45 (d, J=2.0 Hz, 1H), 9.14 (d, J=2.0 Hz, 1H), 8.97 (s, 1H), 8.17 (d, J=8.9 Hz, 1H), 8.01 (d, J=8.8 Hz, 1H), 7.99-7.91 (m, 2H), 7.73 (d, J=8.4 Hz, 2H).

    Step 2: 1-(2-isopropylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]quinolin-7-yl]methyleneamino]thiourea

    [0978] 3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]quinoline-7-carbaldehyde (0.4 g, 1.12 mmol) and 1-amino-3-(2-isopropylphenyl)thiourea (0.23 g, 1.12 mmol) were taken up in Ethanol (12 mL) and the mixture heated to 60° C. for 4 h. The precipitated solid was filtered, washed sequentially with Ethanol and Pentane and dried to afford (0.418 g, 99%) of the title compound as a white solid. LC/MS (method 3): R.sub.t: 3.15 min; MS: m/z=549 (M.sup.+), .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 12.02 (s, 1H), 10.16 (s, 1H), 9.62 (d, J=2.0 Hz, 1H), 8.91 (d, J=2.1 Hz, 1H), 8.77 (s, 1H), 8.38 (s, 1H), 8.03-7.92 (m, 2H), 7.90 (s, 2H), 7.71 (d, J=8.4 Hz, 2H), 7.39 (d, J=7.6 Hz, 1H), 7.32 (ddd, J=12.4, 6.8, 3.8 Hz, 1H), 7.25 (q, J=4.1, 3.2 Hz, 2H), 3.18 (p, J=6.9 Hz, 1H), 1.22 (d, J=6.9 Hz, 6H).

    Example 7: (2Z)-2-(2-isopropylphenyl)imino-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]quinolin-7-yl]methyleneamino]thiazolidin-4-one (compound C-16)

    [0979] To a solution of 3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]quinoline-7-carbaldehyde (0.15 g, 0.42 mmol) in Acetic acid (5 mL) was added 3-amino-2-(2,6-dimethylphenyl)imino-thiazolidin-4-one (0.1 g, 0.42 mmol) and the mixture stirred at ambient temperature for 5 h. The mixture was diluted with a mixture of Ethyl acetate and water and partitioned. The separated organic layer was washed successively with a saturated solution of Sodium bicarbonate, saturated brine, dried (anhydrous Sodium sulphate) and evaporated under reduced pressure. The residue was subjected to silica gel flash column chromatography to obtain the title compound (0.057 g, 22%). LC/MS (method 3): R.sub.t:1.85; MS: m/z=589.6 (M.sup.+), .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ9.49 (d, J=2.0 Hz, 1H), 9.40 (s, 1H), 9.01 (d, J=2.1 Hz, 1H), 8.79 (s, 1H), 8.07 (d, J=8.9 Hz, 1H), 7.94 (d, J=8.5 Hz, 3H), 7.71 (d, J=8.4 Hz, 2H), 7.32 (d, J=7.4 Hz, 1H), 7.16 (m, 2H), 6.89 (d, J=7.5 Hz, 1H), 4.19 (s, 2H), 3.04 (p, J=7.0 Hz, 1H), 1.16 (d, J=6.9 Hz, 6H).

    Example 8: (2Z)-3-(2-isopropylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one (compound C-17)

    [0980] To a solution of 1-(2-isopropylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]quinolin-7-yl]methyleneamino]thiourea (0.2 g, 0.365 mmol) in Ethanol (8 mL) was added Methyl bromoacetate (0.22 g, 1.46 mmol) and Sodium acetate (0.09 g, 1.09 mmol). The reaction mixture stirred for 5 h at 40° C. and subsequently cooled and partitioned with Ethyl acetate and water. The organic layer was separated dried (anhydrous Sodium sulphate) and evaporated under reduced pressure. The residue was purified by silica gel flash column chromatography to afford the title compound (0.12 g, 96%). LC/MS (method 3): R.sub.t: 3.27 min; MS: m/z=589 (M.sup.+), .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ9.38 (d, J=2.0 Hz, 1H), 8.76 (s, 1H), 8.72 (d, J=2.1 Hz, 1H), 8.58 (s, 1H), 8.01-7.84 (m, 4H), 7.70 (d, J=8.4 Hz, 2H), 7.51 (q, J=8.1, 7.7 Hz, 2H), 7.41-7.33 (m, 1H), 7.30 (d, J=8.0 Hz, 1H), 4.40-4.10 (m, 2H), 2.91-2.76 (m, 1H), 1.17 (dd, J=11.2, 6.8 Hz, 6H).

    Example 9: 1-(2-isopropylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin-7-yl]methyleneamino]thiourea (compound C-24)

    Step 1: N-[(3-bromophenyl)methyl]-1, 1-dimethoxy-propan-2-amine

    [0981] To a solution of 3-bromo benzyl amine (4 g, 21.62 mmol) in Dichloroethane (60 mL) was added Pyruvic aldehyde dimethyl acetal (2.6 g, 21.62 mmol) and Sodium triacetoxyborohydride (6.4 g, 30.19 mmol). The mixture was stirred at ambient temperature for 16 h. A solution of Sodium hydroxide (2N) was added and the mixture partitioned. The aqueous layer was extracted with Dichloromethane (2×80 mL). The combined organic extracts were washed with brine (40 mL), dried (anhydrous Sodium sulphate) and concentrated under reduced pressure to afford 9.5 g (Quantitative) of the title compound as an oil. LCMS (method 3): R.sub.t: 1.56 min; MS: m/z=288.1 (M.sup.+). .sup.1H NMR (300 MHz, DMSO-d.sub.6) 1H NMR (300 MHz, DMSO-d6) δ 7.54 (t, J=1.7 Hz, 1H), 7.40 (m, 1H), 7.37-7.20 (m, 2H), 4.09 (d, J=5.8 Hz, 1H), 3.84-3.57 (m, 2H), 3.29 (s, 3H), 3.25 (s, 3H), 2.63 (p, J=6.3 Hz, 1H), 1.89 (d, J=37.5 Hz, 1H), 0.94 (d, J=6.4 Hz, 3H).

    Step 2: 7-bromo-3-methyl-isoquinoline

    [0982] Chlorosulfonic acid (38.6 g, 346 mmol) was cooled to 0° C. and N-[(3-bromophenyl)methyl]-1,1-dimethoxy-propan-2-amine (9.5 g, 33.10 mmol) was added drop wise and the mixture heated to 100° C. for 1 h. The mixture was subsequently cooled to ambient temperature, poured into a mixture of ice and water and extracted the Methyl t-butyl ether (2×60 mL). The aqueous layer was cooled to ˜5° C. and basified with Sodium hydroxide solution. Then basified solution was then extracted with Dichloromethane (2×100 mL). The combined Dichloromethane extracts were dried (anhydrous Sodium sulphate) and concentrated under reduced pressure and the residue purified by silica gel flash chromatography (eluent 12-15% Ethyl acetate in heptane) to afford 4.2 g (57%) of the title compound as a yellow solid. LC/MS (method 3): R.sub.t: 2.30 min; MS: m/z=222.1 (M.sup.+). .sup.1H NMR (300 MHz, CDCl.sub.3) δ 9.11 (s, 1H), 8.10 (d, J=1.9 Hz, 1H), 7.72 (dd, J=8.8, 1.9 Hz, 1H), 7.62 (d, J=8.8 Hz, 1H), 7.48 (s, 1H), 2.70 (s, 3H).

    Step 3: 7-bromo-3-methyl-8-nitro-isoquinoline

    [0983] To a solution of 7-bromo-3-methyl-isoquinoline (4.2 g, 19 mmol) in concentrated Sulphuric acid (24 mL) was added Potassium nitrate (1.93 g, 19 mmol) portion wise at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 4 h. The mixture was subsequently poured into ice and neutralized using aqueous Ammonia solution. The precipitated solid was filtered and the filter cake washed with water (10 mL) and Diethyl ether (10 mL). The solid was purified by silica gel flash chromatography (eluent 15-18% Ethyl acetate in heptane) to afford 3.2 g (63%) of the title compound. LC/MS (method 3): R.sub.t: 2.7 min; MS: m/z=267 (M.sup.+). .sup.1H NMR (300 MHz, CDCl.sub.3) δ 9.06 (s, 1H), 7.81 (d, J=8.9 Hz, 1H), 7.74 (d, J=8.9 Hz, 1H), 7.55 (s, 1H), 2.73 (s, 3H).

    Step 4: 3-methyl-8-nitro-N-[4-(trifluoromethoxy)phenyl]isoquinolin-7-amine

    [0984] To a suspension of NaH (0.43 g, 18.mmol) in Tetrahydrofuran (35 mL) at 0° C. was added 4-trifluromethoxy aniline (2.4 g, 13.5 mmol) and heated at 60° C. for 30 min. 7-bromo-3-methyl-8-nitro-isoquinoline (3.2 g, 12.03 mmol) was added and the mixture was maintained at 60° C. for 12 h. The mixture was cooled to ambient temperature, diluted with water (25 mL), extracted with Ethyl acetate (2×40 mL). The combined organic extracts were dried (anhydrous Sodium sulphate) and concentrated under reduced pressure. The residue was triturated with Diethyl ether (10 mL) to afford 2.9 g (67%) of the title compound. LC/MS (method 3): R.sub.t: 2.9 min; MS: m/z=364.1 (M.sup.+). .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 9.54 (s, 1H), 9.36 (s, 1H), 7.97 (d, J=9.3 Hz, 1H), 7.68 (s, 1H), 7.59 (d, J=9.2 Hz, 1H), 7.38 (s, 4H), 2.60 (s, 3H).

    Step 5: 3-methyl-N7-[4-(trifluoromethoxy)phenyl]isoquinoline-7,8-diamine

    [0985] To a solution of 3-methyl-8-nitro-N-[4-(trifluoromethoxy)phenyl]isoquinolin-7-amine (8.8 gm, 24.2 mmol) in methanol (160 mL) was added Stannous chloride dehydrate (27.34 g, 121.17 mmol) and the mixture heated at 85° C. for 12 h. The volatiles were removed under reduced pressure and the residue diluted with water (100 mL), Ethyl acetate (200 ml) and saturated Sodium bicarbonate solution (100 mL). The mixture was filtered through Celite. The filtrate was partitioned and the organic layer was dried (anhydrous Sodium sulphate) and evaporated under reduced pressure. The residue was purified by silica gel flash chromatography (eluent 18-20% ethyl acetate in heptane) to afford 7 g (87%) of the title compound. LC/MS (method 3): R.sub.t: 2.16 min; MS: m/z=334.2 (M.sup.+1). .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 9.43 (s, 1H), 7.58 (s, 1H), 7.42 (s, 1H), 7.36 (d, J=8.5 Hz, 1H), 7.10 (d, J=8.5 Hz, 2H), 7.01 (d, J=8.5 Hz, 1H), 6.70-6.57 (m, 2H), 5.83 (s, 2H), 2.55 (s, 3H).

    Step 6: 7-methyl-3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinoline

    [0986] A solution of 3-methyl-N7-[4-(trifluoromethoxy)phenyl]isoquinoline-7,8-diamine (7.0 g, 21 mmol) in formic acid (40 mL) was stirred at ambient temperature for 12 h. The mixture was evaporated under reduced pressure and the residue diluted with water (50 mL) and neutralized using Sodium bicarbonate solution. The mixture was extracted with Ethyl acetate (2×100 mL) and the organic extracts separated and drived (anhydrous Sodium sulphate) and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (eluent 20-22% Ethyl acetate in Heptane) to afford 4.2 g (58%) of title compound. LC/MS (method 3): R.sub.t: 2.22 min; MS: m/z=344.2 (M.sup.+1). .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 9.77 (s, 1H), 8.75 (s, 1H), 7.98 (d, J=8.9 Hz, 1H), 7.95-7.88 (m, 2H), 7.80 (s, 1H), 7.77 (d, J=9.1 Hz, 1H), 7.69 (d, J=8.5 Hz, 2H), 2.66 (s, 3H).

    Step 7: 7-methyl-3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin N-oxide

    [0987] To a solution of 7-methyl-3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinoline (2.5 g, 7.28 mmol) in Dichloromethane (25 mL) was added m-chloroperbenzoic acid (1.89 g, 10.95 mmol) and stirred for 12 h. The mixture was subsequently diluted with water (50 mL), basified with saturated Sodium bicarbonate solution (25 mL) and extracted with Ethyl acetate (2×80 mL). The combined organic extracts were dried (anhydrous Sodium sulphate) and concentrated and the residue triturated with pentane to afford 2.5 g (96%) of the title compound. LC/MS (method 3): R.sub.t: 1.38 min; MS: m/z=360.3 (M.sup.+). .sup.1H NMR (300 MHz, CDCl.sub.3) δ 10.21 (s, 1H), 8.40 (s, 1H), 8.06 (s, 1H), 8.00 (d, J=8.9 Hz, 1H), 7.81 (d, J=9.0 Hz, 1H), 7.64 (d, J=8.7 Hz, 2H), 7.53 (d, J=8.4 Hz, 2H), 2.96 (s, 3H).

    Step 8: [3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin-7-yl]methyl acetate

    [0988] A solution of 7-methyl-3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin N-oxide (2.5 g, 6.96 mmol) in Acetic anhydride (25 mL) was heated at 140° C. for 12 h. The mixture was cooled to ambient temperature and the volatiles were removed invacuo. The residue was purified by silica gel flash chromatography (eluent 5-8% Methanol in Dichloromethane) to afford 2.6 g (93%) of the title compound. LC/MS (method 3): R.sub.t: 1.55 min; MS: m/z=402.4 (M.sup.+). .sup.1H NMR (300 MHz, DMSO-d.sub.6) 1H NMR (300 MHz, DMSO-d6) δ 9.85 (s, 1H), 8.81 (s, 1H), 8.80 (s, 1H), 8.12-8.00 (m, 2H), 7.94 (m, 2H), 7.70 (m, 2H), 5.34 (s, 2H), 2.16 (s, 3H).

    Step 9: [3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin-7-yl]methanol

    [0989] To a solution of [3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin-7-yl]methyl acetate (2.6 g, 6.48 mmol) in Tetrahydrofuran (15 mL) and water (10 mL) was added a solution of Lithium hydroxide monohydrate (0.409 g, 9.74 mmol) in water (1 mL). The mixture was stirred for 4 h and subsequently diluted with water (30 mL), acidified with 1N HCl and extracted with Ethyl acetate (2×50 mL). The combined organic extracts were dried (anhydrous Sodium sulphate) and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (eluent 25-30% Ethyl acetate in Heptane) to afford 1.0 g (43.1%) of title compound. LC/MS (method 3): R.sub.t: 1.29 min; MS: m/z=360 (M.sup.+). .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 9.80 (s, 1H), 8.77 (s, 1H), 8.06-7.98 (m, 2H), 7.97-7.91 (m, 2H), 7.89 (d, J=9.1 Hz, 1H), 7.69 (d, J=8.5 Hz, 2H), 5.52 (t, J=5.8 Hz, 1H), 4.79 (d, J=5.6 Hz, 2H).

    Step 10: 3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinoline-7-carbaldehyde

    [0990] To a solution of [3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin-7-yl]methanol (1.0 g, 2.78 mmol) in Dichloromethane (15.0 mL) was added Dess-Martin periodinane (3.54 g, 8.34 mmol) and the mixture stirred at ambient temperature for 12 h. Sodium thiosulphate solution (20 mL) was subsequently added and the mixture extracted with Dichloromethane (2×30 mL). The combined organic extracts were dried (anhydrous Sodium sulphate) concentrated under reduced pressure and the residue purified by silica gel flash column chromatography (eluent 24-25% Ethyl acetate in Heptane) to afford 0.8 g (80%) of the title compound. LC/MS (method 3): R.sub.t: 1.53 min; MS: m/z=358 (M.sup.+).1H NMR (300 MHz, DMSO-d.sub.6) δ 10.21 (s, 1H), 10.03 (s, 1H), 8.91 (s, 1H), 8.69 (s, 1H), 8.17 (s, 2H), 7.97 (m, 2H), 7.71 (m, 2H).

    Step 11: 1-(2-isopropylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin-7-yl]methyleneamino]thiourea (C-24)

    [0991] To a solution of 3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinoline-7-carbaldehyde (0.2 g, 0.56 mmol) in Ethanol (3 mL) was added 1-amino-3-(2-isopropylphenyl)thiourea (0.117 g, 0.56 mmol) and the mixture heated at 85° C. for 2 h. The mixture was cooled and the precipitated solids were filtered, washed with cold Ethanol (2 mL) and triturated with n-pentane (5 mL) and dried to afford the title compound 0.180 g (59%). LC/MS (method 3): R.sub.t: 1.78 min; MS: m/z=549 (M.sup.+1). .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 10.10 (s, 1H), 9.86 (s, 1H), 9.00 (s, 1H), 8.82 (s, 1H), 8.43 (s, 1H), 8.07 (d, J=8.9 Hz, 1H), 8.01 (s, 2H), 7.81 (d, J=9.0 Hz, 1H), 7.69 (d, J=8.5 Hz, 2H), 7.39 (d, J=7.6 Hz, 1H), 7.37-7.28 (m, 1H), 7.25 (d, J=4.1 Hz, 2H), 3.17 (p, J=6.9 Hz, 1H), 1.21 (d, J=6.9 Hz, 6H).

    Example 10: (2Z)-3-(2-isopropylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin-7-yl]methylenehydrazono]thiazolidin-4-one (compound C-26)

    [0992] To a solution of 1-(2-isopropylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin-7-yl]methyleneamino]thiourea (0.130 g, 0.237 mmol) in Ethanol (5 mL), Sodium acetate (0.058 g, 0.71 mmol) and Methyl bromo acetate (0.073 g, 0.477 mmol) were added. and the mixture stirred at 40° C. for 12 h. The mixture was subsequently cooled to ambient temperature, diluted with water (15 mL) and extracted with Ethyl acetate (2×15 mL). The combined extracts were dried (anhydrous Sodium sulphate), evaporated and the residue purified by silica gel column chromatography (eluent 35-40% Ethyl acetate in Heptane) to afford 0.078 g (56%) of the title compound. LC/MS (method 1): R.sub.t: 1.88 min; MS: m/z=589.6 (M.sup.+). .sup.1H NMR (300 MHz, DMSO-d.sub.6) 1H NMR 6 9.90 (s, 1H), 8.84 (s, 1H), 8.53 (s, 1H), 8.41 (s, 1H), 8.06 (m, 2H), 8.00-7.86 (m, 2H), 7.70 (d, J=8.4 Hz, 2H), 7.52 (m, 2H), 7.36 (m, H), 7.30 (dd, J=7.9, 1.5 Hz, 1H), 4.43-4.09 (m, 2H), 2.81 (p, J=6.9 Hz, 1H), 1.16 (dd, J=12.5, 6.8 Hz, 6H).

    Example 11: (2Z)-2-(2-isopropylphenyl)imino-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinolin-7-yl]methyleneamino]thiazolidin-4-one (compound C-28)

    [0993] To a solution of 3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-h]isoquinoline-7-carbaldehyde (0.2 g, 0.56 mmol) in acetic acid (3.0 mL) was added 3-amino-2-(2,6-dimethylphenyl)imino-thiazolidin-4-one (0.139 g, 0.56 mmol) and stirred at room temperature for 12 h. The mixture was diluted with water (10 mL) and neutralized with saturated Sodium bicarbonate solution and extracted with Ethyl acetate (2×25 mL). The combined organic extracts were dried (anhydrous Sodium sulphate) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluent 70-75% Ethyl acetate in heptane) to afford 0.040 g (12%) of the title compound LC/MS (method 1): R.sub.t: 1.83 min; MS: m/z=589.6 (M.sup.+). .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 9.90 (s, 1H), 8.84 (s, 1H), 8.53 (s, 1H), 8.40 (s, 1H), 8.09 (d, J=9.0 Hz, 1H), 8.03 (d, J=9.1 Hz, 1H), 7.94 (d, J=8.9 Hz, 2H), 7.70 (d, J=8.5 Hz, 2H), 7.59-7.45 (m, 2H), 7.42-7.33 (m, 1H), 7.29 (d, J=7.7 Hz, 1H), 4.39-4.09 (m, 2H), 2.90-2.76 (m, 1H), 1.16 (dd, J=12.4, 6.8 Hz, 6H).

    Example 12: 1-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]-N-[(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]oxy-methanimine (compound C-33)

    [0994] A mixture of 3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoline-7-carbaldehyde (0.15 g, 0.42 mmol) and O-[(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]hydroxylamine (0.093 g, 0.42 mmol) in EtOH (10 mL) was heated at 60° C. for 12 h. The mixture was cooled to ambient temperature and the solid precipitated was collected by filtration and washed with EtOH, dried under vacuum to get the title compound as an off-white solid. (0.120 g, 77%) LC/MS (method 1): R.sub.t: 1.196 min; MS: m/z=561.2 (M.sup.+). .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 8.9 (m, 1H), 8.8 (s, 1H), 8.53 (s, 1H), 8.15 (m, 1H), 8.05 (m, 1H), 7.95 (m, 4H), 7.75 (m, 1H), 5.6 (m, 1H), 3.85 (m, 1H), 3.3 (m, 4H), 3.55 (m, 7H), 3.05 (m, 1H), 1.1 (m, 3H).

    Example 13: 1-(2-isopropylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoxalin-7-yl]methyleneamino]thiourea (compound C-35)

    Step 1: Ethyl N-(3-chloro-2-nitro-phenyl)carbamate

    [0995] A solution of 3-chloro-2-nitro aniline (0.52 g, 3.01 mmol) in Ethyl chloroformate (4 mL) was heated at 110° C. for 2 h. The volatiles were distilled out and the residue diluted with water and extracted with Ethyl acetate (2×20 mL), the combined organic layer washed with Sodium bicarbonate solution, water and brine solution. The organic layer were dried over Sodium sulfate and concentrated under reduced pressure and the residue washed with n-heptane to get the pure product (0.42 g, Yield: 57%) as a pale orange solid. .sup.1H NMR (300 MHz, CDCl.sub.3) δ 8.12 (dd, J=8.5, 1.1 Hz, 1H), 7.50 (s, 1H), 7.42 (t, J=8.3 Hz, 1H), 7.22 (dd, J=8.1, 1.2 Hz, 1H), 4.24 (q, J=7.1 Hz, 2H), 1.32 (t, J=7.1 Hz, 3H).

    Step 2: Ethyl N-[2-nitro-3-[4-(trifluoromethoxy)anilino]phenyl]carbamate

    [0996] A solution of Ethyl N-(3-chloro-2-nitro-phenyl)carbamate (0.2 g, 0.81 mmol) in Toluene (4 mL) was degassed with nitrogen gas for 20 min, BINAP (0.05 g, 0.08 mmol), Pd(OAc).sub.2 (0.03 g, 0.13 mmol) and Cesium carbonate (0.4 g, 1.23 mmol) were added. The mixture was degassed for 10 minutes, and 4-trifluoromethoxy aniline (0.150 g, 0.85 mmol) was added and again degassing was done for 10 minutes. The mixture was heated at 110° C. for 1 h, cooled to ambient temperature and filtered through Celite, the filtrate diluted with water (15 mL) and extracted with ethyl acetate (2×15 mL). The organic layers were separated and dried over sodium sulfate and concentrated under reduced pressure and the residue purified by silica gel column chromatography (eluent ethyl acetate (2%) and heptane (98%) to get the title compound (0.140 g, Yield: 44%). LC/MS: R.sub.t: 3.39 min; MS: m/z=384.1 (M.sup.−), .sup.1H NMR (300 MHz, CDCl.sub.3) δ 9.52 (s, 1H), 8.98 (s, 1H), 7.80 (dd, J=8.3, 1.2 Hz, 1H), 7.33 (d, J=8.4 Hz, 1H), 7.26-7.29 (m, 4H), 6.85 (dd, J=8.6, 1.2 Hz, 1H), 4.27 (q, J=7.1 Hz, 2H), 1.36 (t, J=7.1 Hz, 3H).

    Step 3: Ethyl N-[2-amino-3-[4-(trifluoromethoxy)anilino]phenyl]carbamate

    [0997] To a stirred solution of Ethyl N-[2-nitro-3-[4-(trifluoromethoxy)anilino]phenyl]carbamate (0.140 g, 0.36 mmol) in Ethyl acetate (5 mL) was added tin chloride dihydrate (0.246 g, 1.09 mmol) at ambient temperature and heated at 80° C. for 4 h. The reaction cooled to rt and Sodium bicarbonate solution (15 mL) was added. The mixture was filtered through celite, the filtrate was diluted with Ethyl acetate and partitioned. The organic layers were washed with water, brine solution, dried (anhydrous Sodium sulphate) and concentrated under reduced pressure. The residue was triturated with n-Pentane to get the title compound (0.095 g, 73%) as a pale brown solid. LC/MS: R.sub.t: 2.89 min; MS: m/z=356.2 (M.sup.+), .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 8.64 (s, 1H), 7.48 (s, 1H), 7.10 (d, J=8.8 Hz, 3H), 6.85 (dd, J=7.8, 1.4 Hz, 1H), 6.75-6.63 (m, 2H), 6.54-6.59 (m, 1H), 4.58 (s, 2H), 4.10 (q, J=7.1 Hz, 2H), 1.33-1.17 (m, 3H).

    Step 4: Ethyl N-[1-[4-(trifluoromethoxy)phenyl]benzimidazol-4-yl]carbamate

    [0998] A solution of Ethyl N-[2-amino-3-[4-(trifluoromethoxy)anilino]phenyl]carbamate (0.120 g, 0.34 mmol) in Formic acid (4 mL) was heated at 80° C. for 4 h. The volatiles were evaporated under vacuum and Sodium bicarbonate solution (15 mL) was added and the mixture extracted with Ethyl acetate (2×15 mL). The combined organic extracts were dried over Sodium sulfate and concentrated under reduced pressure to get a residue which was purified by silica gel column chromatography (eluent 12%:Ethyl acetate in Heptane) to get the title compound (0.08 g, Yield: 64.8%). LC/MS: R.sub.t: 3.10 min; MS: m/z=366.2 (M.sup.+), .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 9.04 (s, 1H), 8.57 (s, 1H), 7.91-7.79 (m, 2H), 7.70 (dd, J=6.8, 2.0 Hz, 1H), 7.64 (d, J=8.5 Hz, 2H), 7.37-7.21 (m, 2H), 4.18 (q, J=7.1 Hz, 2H), 1.26 (t, J=7.1 Hz, 3H).

    Step 5: Ethyl N-[5-nitro-1-[4-(trifluoromethoxy)phenyl]benzimidazol-4-yl]carbamate

    [0999] To a stirred solution of Ethyl N-[1-[4-(trifluoromethoxy)phenyl]benzimidazol-4-yl]carbamate (0.05 g, 0.14 mmol) in con.sulfuric acid (2 mL) was added Potassium nitrate (0.02 g, 0.16 mmol) at rt and stirred for 2 h. The reaction mixture was neutralized with sodium bicarbonate solution and extracted with Ethyl acetate. The organic layers were dried over sodium sulfate and concentrated under reduced pressure and the residue purified by silica gel column chromatography (eluent Ethyl acetate (22%) in Heptane) to obtain the title compound (0.02 g, Yield: 36%). LC/MS: R.sub.t: 2.84 min; MS: m/z=411 (M.sup.+), .sup.1H NMR (300 MHz, DMSO-6) δ 10.10 (s, 1H), 8.81 (s, 1H), 8.08-7.84 (m, 3H), 7.68 (d, J=8.4 Hz, 2H), 7.55 (d, J=9.0 Hz, 1H), 4.11 (q, J=7.1 Hz, 2H), 1.22 (t, J=7.1 Hz, 3H).

    Step 6: 5-nitro-1-[4-(trifluoromethoxy)phenyl]benzimidazol-4-amine

    [1000] To a solution of Ethyl N-[5-nitro-1-[4-(trifluoromethoxy)phenyl]benzimidazol-4-yl]carbamate (0.05 g, 0.12 mmol) in Ethanol (3 mL) was added a solution of Potassium hydroxide (0.120 g, 2.139 mmol) in water (1.5 mL) at rt and the mixture heated at 100° C. for 4 h. The mixture was cooled to ambient temperature, diluted with water and neutralized with Hydrochloric acid solution (1N) and subsequently extracted with Ethyl acetate (2×5 mL). The combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to get a residue which was purified by neutral alumina column chromatography to obtain the title compound (0.030 g, 72%). LC/MS: R.sub.t: 2.899 min; MS: m/z=339 (M.sup.+), .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 8.60 (s, 1H), 7.97 (d, J=9.4 Hz, 1H), 7.95-7.78 (m, 4H), 7.67 (d, J=8.4 Hz, 2H), 6.85 (d, J=9.4 Hz, 1H).

    Step 7: 1-[4-(trifluoromethoxy)phenyl]benzimidazole-4,5-diamine

    [1001] To a stirred solution of 5-nitro-1-[4-(trifluoromethoxy)phenyl]benzimidazol-4-amine (0.1 g, 0.3 mmol) in Ethyl acetate (5 mL) was added tin chloride dihydrate (0.270 g, 1.18 mmol) at RT and heated at 80° C. for 2 h. The mixture was cooled to ambient temperature and a solution of sodium bicarbonate solution was added and the, then filtered through celite. The filtrate was extracted with Ethyl acetate and the Ethyl acetate extracts washed successively with water, brine and dried over anhydrous Sodium sulphate and evaporated invacuo to obtain the title compound as a brown solid (0.09 g, Yield: 95%). LC/MS: R.sub.t: 1.184 min; MS: m/z=309.2 (M.sup.+), .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 8.27 (s, 1H), 7.84-7.71 (m, 2H), 7.58 (d, J=8.5 Hz, 2H), 6.77-6.59 (m, 2H), 4.71 (s, 4H).

    Step 8: Ethyl 3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoxaline-7-carboxylate

    [1002] To a stirred solution of 1-[4-(trifluoromethoxy)phenyl]benzimidazole-4,5-diamine (2.4 g, 7.79 mmol) in N-Methyl pyrrolidone (20 mL) was added Ethyl bromo pyruvate (1.5 g, 7.7 mmol) at RT and the mixture was stirred at rt for 12 h. The reaction mixture was diluted with water and extracted with Ethyl acetate and the extracts dried over anhydrous Sodium sulphate and concentrated under reduced pressure The resulting residue was purified by silica gel column chromatography (eluent 45% Ethyl acetate in Heptane) to get the title compound (0.875 g, 28%), LC/MS: R.sub.t: 2.836 min; MS: m/z=403 (M.sup.+), .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 9.49 (s, 1H), 8.91 (s, 1H), 8.24 (d, J=9.1 Hz, 1H), 8.06 (d, J=9.1 Hz, 1H), 8.03-7.91 (m, 2H), 7.72 (d, J=8.4 Hz, 2H), 4.52 (q, J=7.1 Hz, 2H), 1.45 (t, J=7.1 Hz, 3H).

    Step 9: [3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoxalin-7-yl]methanol

    [1003] To a stirred solution of Ethyl 3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoxaline-7-carboxylate (0.05 g, 0.12 mmol) in Dichloromethane (3 mL) and Methanol (3 mL) mixture was added Sodium borohydride (0.056 g, 1.49 mmol) at rt and stirred for 1 h. The reaction mixture was diluted with water and extracted with Ethyl acetate and the extracts washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was triturated with Diethyl ether to get the desired product as an off-white solid (0.04 g, Yield: 89%). LC/MS: R.sub.t: 2.226 min; MS: m/z=361 (M.sup.+), .sup.1H NMR (300 MHz, CDCl.sub.3) δ 8.96 (s, 1H), 8.38 (s, 1H), 8.06 (d, J=9.1 Hz, 1H), 7.87 (d, J=9.1 Hz, 1H), 7.71-7.62 (m, 2H), 7.52 (d, J=8.5 Hz, 2H), 5.1 (s, 2H), 3.4 (s, 1H).

    Step 10: 3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoxaline-7-carbaldehyde

    [1004] To a stirred solution of [3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoxalin-7-yl]methanol (0.04 g, 0.1 mmol) in Dichloromethane (3 mL) was added Dess-Martin Periodinone (0.081 g, 0.191 mmol) at 0° C. and stirred for 3 h. Sodium thiosulphate solution and water were added and the mixture extracted with Ethyl acetate. The organic extracts were dried over anhydrous Sodium sulphate and evaporated and the resulting residue was purified by washing with diethyl ether and n-heptane, to afford the desired product (0.03 g, 86%) as white solid. LC/MS: R.sub.t: 1.499 min; MS: m/z=359.4 (M.sup.+), .sup.1H NMR (300 MHz, DMSO-d.sub.6) 1H NMR (300 MHz, DMSO-d6) δ 10.33 (s, 1H), 9.40 (s, 1H), 8.94 (s, 1H), 8.28 (d, J=9.1 Hz, 1H), 8.09 (d, J=9.1 Hz, 1H), 8.04-7.91 (m, 2H), 7.73 (d, J=8.4 Hz, 2H).

    Step 11: 1-(2-isopropylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoxalin-7-yl]methyleneamino]thiourea

    [1005] To a stirred solution of 3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoxaline-7-carbaldehyde (0.25 g, 0.7 mmol) in Ethanol (6 mL) was added 1-amino-3-(2-isopropylphenyl)thiourea (0.145 g, 0.7 mmol) at rt and the mixture heated at 80° C. for 2 h. The reaction mixture was cooled to 0° C. and stirred for 20 min to precipitate out a solid which was filtered, washed with cold Ethanol and dried to afford the desired product (0.2 g, 52%) as a pale yellow solid. LC/MS: R.sub.t: 1.803 min; MS: m/z=550.6 (M.sup.+), .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 12.32 (s, 1H), 10.41 (s, 1H), 10.01 (s, 1H), 8.85 (s, 1H), 8.48 (s, 1H), 8.06 (d, J=9.1 Hz, 1H), 8.03-7.89 (m, 4H), 7.71 (d, J=8.4 Hz, 2H), 7.44-7.17 (m, 3H), 3.16 (p, J=6.9 Hz, 1H), 1.21 (d, J=6.9 Hz, 6H).

    Example 14: 3-(2-isopropylphenyl)-2-[[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoxalin-7-yl]methylenehydrazono]thiazolidin-4-one (compound C-34)

    [1006] To a stirred solution of 1-(2-isopropylphenyl)-3-[[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinoxalin-7-yl]methyleneamino]thiourea (0.170 g, 0.31 mmol) in Ethanol (5 mL) were added Methyl bromoacetate (0.24 g, 1.56 mmol) and Sodium acetate (0.076 g, 0.92 mmol) and stirred at rt for 24 h. The mixture was diluted with water and extracted with Dichloromethane, the organic layers partitioned and dried (anhydrous Sodium sulphate) and evaporated under reduced pressure to get a residue which was purified by silica gel column chromatography (eluent: 3% Methanol in Dichloromethane) to obtain the title compound (0.130 g, 68%). LC/MS: R.sub.t: 3.314 min; MS: m/z=590 (M.sup.+), .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ 9.48 (s, 1H), 8.84 (s, 1H), 8.47 (s, 1H), 8.12 (d, J=8.9 Hz, 1H), 8.01 (d, J=9.0 Hz, 1H), 7.99-7.88 (m, 2H), 7.71 (d, J=8.3 Hz, 2H), 7.62-7.46 (m, 2H), 7.44-7.27 (m, 2H), 4.43-4.17 (m, 2H), 2.82 (p, J=6.9 Hz, 1H), 1.18 (dd, J=17.5, 6.8 Hz, 6H).

    Example 15: 1-(2-isopropylphenyl)-3-[(E)-[2-methyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-f]quinazolin-7-yl]methyleneamino]thiourea (compound C-36)

    Step 1: 2-methyl-7,8-dihydro-6H-quinazolin-5-one

    [1007] 2-(dimethylaminomethylene)cyclohexane-1,3-dione (11.8 g, 70.62 mmol) and Acetamidine hydrochloride (7.35 g, 77.74 mmol) was taken up in EtOH (100 mL) and heated to reflux. Diisopropyl ethyl amine (10.95 g, 84.71 mmol) was added drop wise in 20 min and the mixture was refluxed for a further 3 h. The mixture was cooled to ambient temperature, poured into ice water (100 mL) and acidified with acetic acid. The resulting suspension was stirred for 30 min and extracted with Ethyl acetate (2×100 mL). The combined organic extracts were partitioned and dried over anhydrous Sodium sulphate and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (eluent 2-4% MeOH in Dichloromethane) to afford 6 g (52% yield) of the title compound as a yellowish solid. LC/MS (method 3): R.sub.t: 0.87 min; MS: m/z=163 (M.sup.+1); .sup.1H NMR (300 MHz, DMSO-d.sub.6); δ 8.79 (s, 1H), 2.84 (t, J=6.2 Hz, 2H), 2.50 (s, 3H), 2.36 (p, J=1.9 Hz, 1H), 1.95 (p, J=6.4 Hz, 2H), 1.76 (s, 1H).

    Step 2: 2-methyl-6-[4-(trifluoromethoxy)benzoyl]-7,8-dihydro-6H-quinazolin-5-one

    [1008] To a solution of 2-methyl-7,8-dihydro-6H-quinazolin-5-one (1.5 g, 9.25 mmol) in Toluene (10 mL) at ambient temperature was added Lithium Hexamethyldisilazide (2.32 g, 13.87 mmol) and stirred for 10 min This mixture was subsequently added to a solution of 4-trifluromethoxy benzoyl chloride (2.079 g, 9.25 mmol) in toluene drop wise and stirred for a further 30 min. Subsequently, water (25 mL) was added and the mixture extracted with Ethyl acetate (2×50 mL). The combined organic extracts were dried (anhydrous Sodium sulphate), concentrated under reduced pressure and the residue purified by flash chromatography (Eluent 40-45% Ethyl acetate in heptane) to afford 1.5 g (46%) of the title compound. LC/MS (method 3): R.sub.t: 1.52 min; MS: m/z=351 (M.sup.+1).

    Step 3: 2,7-dimethyl-3-[4-(trifluoromethoxy)phenyl]-4,5-dihydropyrazolo[3,4-f]quinazoline

    [1009] To a solution of 2-methyl-6-[4-(trifluoromethoxy)benzoyl]-7,8-dihydro-6H-quinazolin-5-one (1.5 g, 4.28 mmol) in EtOH (15 mL) was added Methyl hydrazine sulfate (0.93 g, 6.42 mmol) and triethylamine (0.65 g, 6.43 mmol) and was heated to reflux for 2 h. The mixture was subsequently cooled to ambient temperature, diluted with water (25 mL) and extracted with Ethyl acetate (2×40 mL). The combined organic extracts were dried (anhydrous Sodium sulphate), evaporated invacuo and the residue purified by silica gel flash column chromatography (eluent 1-2% Methanol in Dichloromethane) to afford 0.28 g (18%) of the title compound. LC/MS (method 3): R.sub.t: 1.597 min; MS: m/z=361 (M.sub.+1); .sup.1H NMR (300 MHz, CDCl.sub.3); δ 9.01 (s, 1H), 7.40 (t, J=7.5 Hz, 4H), 3.89 (s, 3H), 3.12 (t, J=7.4 Hz, 2H), 2.85 (t, J=7.5 Hz, 2H), 2.78 (s, 3H).

    Step 4: 2,7-dimethyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-f]quinazoline

    [1010] To a solution of 2,7-dimethyl-3-[4-(trifluoromethoxy)phenyl]-4,5-dihydropyrazolo[3,4-f]quinazoline (0.25 g, 0.694 mmol) in Dichloromethane (6 mL) at 0° C. was added 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (0.24 g, 1.03 mmol) and stirred at ambient temperature for 12 h. The mixture was subsequently evaporated and the residue triturated with n-Pentane to afford 0.230 g (92%) of the title compound. LC/MS (method 1): R.sub.t: 1.61 min; MS: m/z=359 (M.sup.+1). .sup.1H NMR (300 MHz, CDCl.sub.3); δ 9.99 (s, 1H), 7.97 (d, J=9.0 Hz, 1H), 7.71 (d, J=9.3 Hz, 1H), 7.66-7.55 (m, 2H), 7.48 (d, J=8.3 Hz, 2H), 4.24 (s, 3H), 3.05 (s, 3H).

    Step 5: 2-methyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-f]quinazoline-7-carbaldehyde

    [1011] 2,7-dimethyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-f]quinazoline (0.23 g, 0.64 mmol) was dissolved in 1,4-dioxane (4 mL) and Selenium Dioxide (0.107 g, 0.96 mmol) was added and the mixture heated at 110° C. for 12 h. The reaction was cooled to ambient temperature and Water (20 mL) was added and the mixture extracted with Ethyl acetate (2×25 mL). The combined organic extracts were dried (anhydrous Sodium sulphate) and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent 2% Methanol in Dichloromethane) to afford 0.170 g (70%) of the title compound as a solid. LC/MS (method 3): R.sub.t: 1.59 min; MS: m/z=373 (M.sup.+).

    Step 6: 1-(2-isopropylphenyl)-3-[(E)-[2-methyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-f]quinazolin-7-yl]methyleneamino]thiourea

    [1012] 2-methyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-f]quinazoline-7-carbaldehyde (0.170 g, 0.45 mmol) was dissolved in EtOH (3 mL) and 1-amino-3-(2-isopropylphenyl)thiourea (0.095 g, 0.96 mmol) was added and the mixture heated at 85° C. for 2 h. The mixture was cooled to ambient temperature and the precipitated solids were filtered, washed with cold Ethanol (2 mL) and triturated with n-Pentane (5 mL) and dired to afford 0.042 g (16%) of the title compound. LC/MS (method 3): R.sub.t: 1.84 min; MS: m/z=564 (M.sup.+1). .sup.1H NMR (300 MHz, DMSO-d) δ 12.29 (s, 1H), 10.12 (s, 1H), 9.94 (s, 1H), 8.42 (s, 1H), 8.06 (d, J=9.1 Hz, 1H), 7.91 (d, J=8.6 Hz, 2H), 7.66 (d, J=8.3 Hz, 2H), 7.54 (d, J=9.2 Hz, 1H), 7.44-7.13 (m, 4H), 4.24 (s, 3H), 3.14 (q, J=6.8 Hz, 1H), 1.21 (d, J=6.9 Hz, 6H).

    [1013] The compounds summarized in the following table were prepared by analogy to the methods given in Examples 1 to 15:

    TABLE-US-00004 Compound IUPAC-Name: m/z Rt [min] C-1 1-(2,6-dimethylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 535 3.103 5-f]quinolin-7-yl]methyleneamino]thiourea C-2 (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 575 3.317 5-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one C-3 1-(2-isopropylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 549 3.263 5-f]quinolin-7-yl]methyleneamino]thiourea C-4 (2Z)-3-(2-isopropylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 589 3.427 5-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one C-5 1-(2-isopropyl-5-methyl-phenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 563 3.34 5-f]quinolin-7-yl]methyleneamino]thiourea C-6 (2Z)-3-(2-isopropyl-5-methyl-phenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 603 3.558 5-f]quinolin-7-yl]methylenehydrazono]thiazolidin- 4-one C-7 (2Z)-2-(2,6-dimethylphenyl)imino-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 575 3.407 5-f]quinolin-7-yl]methyleneamino]thiazolidin-4-one C-8 (2Z)-2-(2-isopropylphenyl)imino-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 589 3.555 5-f]quinolin-7-yl]methyleneamino]thiazolidin-4-one C-9 (2Z)-3-(2-isopropylphenyl)-4-methyl-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 605 3.326 5-f]quinolin-7-yl]methylenehydrazono]thiazolidin- 4-ol C-10 (2Z)-3-(2-isopropylphenyl)-2-[(E)-[3-[6-(trifluoromethyl)pyridazin-3- 575.2 3.164 yl]imidazo[4,5-f]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one C-11 1-(5-chloro-2-pyridyl)ethyl N-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 528.3 3.13 5-f]quinolin-7-yl]carbamate C-12 (2-isopropyl-5-methyl-cyclohexyl) N-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 527.4 4.105 5-f]quinolin-7-yl]carbamate C-13 1-(2-isopropylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 549 3.15 5-h]quinolin-7-yl]methyleneamino]thiourea C-14 1-(2,6-dimethylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 535 3.0 5-h]quinolin-7-yl]methyleneamino]thiourea C-15 (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 575 3.2 5-h]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one C-16 (2Z)-2-(2-isopropylphenyl)imino-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 589 1.84 5-h]quinolin-7-yl]methyleneamino]thiazolidin-4-one C-17 (2Z)-3-(2-isopropylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 589 3.3 5-h]quinolin-7-yl]methylenehydrazono]thiazolidin-4-one C-18 (2Z)-2-(2,6-dimethylphenyl)imino-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 574 3.19 5-h]quinolin-7-yl]methyleneamino]thiazolidin-4-one C-19 1-(2-isopropylphenyl)-3-[(E)-[2-methyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3, 563.1 1.298 4-f]quinolin-7-yl]methyleneamino]thiourea C-20 (2Z)-3-(2-isopropylphenyl)-2-[(E)-[2-methyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3, 603.1 1.401 4-f]quinolin-7-yl]methylenehydrazono]thiazolidin- 4-one C-21 (E)-3-(2-isopropylphenyl)-N-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 575 3.581 5-f]quinolin-7-yl]methyleneamino]thiazolidin-2-imine C-22 (E)-3-(2-isopropylphenyl)-N-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 589 3.563 5-f]quinolin-7-yl]methyleneamino]-1,3-thiazinan-2- imine C-23 (E)-3-(2,6-dimethylphenyl)-N-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 575 1.86 5-f]quinolin-7-yl]methyleneamino]-1,3-thiazinan-2- imine C-24 1-(2-isopropylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 549 1.779 5-h]isoquinolin-7-yl]methyleneamino]thiourea C-25 1-(2,6-dimethylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 535 1.707 5-h]isoquinolin-7-yl]methyleneamino]thiourea C-26 (2Z)-3-(2-isopropylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 589.6 1.833 5-h]isoquinolin-7-yl]methylenehydrazono]thiazolidin-4- one C-27 (2Z)-3-(2,6-dimethylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 575.6 1.783 5-h]isoquinolin-7-yl]methylenehydrazono]thiazolidin-4- one C-28 (2Z)-2-(2-isopropylphenyl)imino-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 589.6 1.825 5-h]isoquinolin-7-yl]methyleneamino]thiazolidin-4-one C-29 (2Z)-2-(2,6-dimethylphenyl)imino-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 575 1.791 5-h]isoquinolin-7-yl]methyleneamino]thiazolidin-4-one C-30 (E)-3-(2,6-dimethylphenyl)-N-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 561.6 1.865 5-f]quinolin-7-yl]methyleneamino]thiazolidin-2-imine C-31 1-[(E)-[3-[4-(difluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]methyleneamino]- 531.5 1.693 3-(2-isopropylphenyl)thiourea C-32 (2E)-2-[(E)-[3-[4-(difluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7- 571 1.78 yl]methylenehydrazono]-3-(2-isopropylphenyl)thiazolidin-4-one C-33 (E)-1-[3-[4-(trifluoromethoxy)phenyl]imidazo[4,5-f]quinolin-7-yl]-N- 561.2 1.196 [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2- yl]oxy-methanimine C-34 (2Z)-3-(2-isopropylphenyl)-2-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 590 3.314 5-f]quinoxalin-7-yl]methylenehydrazono]thiazolidin-4- one C-35 1-(2-isopropylphenyl)-3-[(E)-[3-[4-(trifluoromethoxy)phenyl]imidazo[4, 550.6 1.803 5-f]quinoxalin-7-yl]methyleneamino]thiourea C-36 1-(2-isopropylphenyl)-3-[(E)-[2-methyl-3-[4-(trifluoromethoxy)phenyl]pyrazolo[3, 564 1.84 4-f]quinazolin-7-yl]methyleneamino]thiourea

    [1014] Biology:

    Example B1: Action on Yellow Fever Mosquito (Aedes aegypti)

    [1015] For evaluating control of yellow fever mosquito (Aedes aegypti) the test unit consisted of 96-well-microtiter plates containing 200 μl of tap water per well and 5-15 freshly hatched A. aegypti larvae.

    [1016] The active compounds were formulated using a solution containing 75% (v/v) water and 25% (v/v) DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect diet at 2.5 μl, using a custom built micro atomizer, at two replications.

    [1017] After application, microtiter plates were incubated at 28+1° C., 80+5% RH for 2 days. Larval mortality was then visually assessed.

    [1018] In this test, compounds C-1, C-2, C-4, C-5, C-6, C-7, C-8, C-9, C-11, C-14, C-15, C-16, C-17, C-19, C-20, C-21, C-22, C-23, C-26, C-27, C-28, C-29 at 800 ppm showed at least 75% mortality in comparison with untreated controls.

    Example B2: Action on Orchid Thrips (Dichromothrips Corbetti)

    [1019] Dichromothrips corbettiadults used for bioassay were obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the test compound is diluted in a 1:1 mixture of acetone:water (vol:vol), plus Kinetic® HV at a rate of 0.01% v/v.

    [1020] Thrips potency of each compound was evaluated by using a floral-immersion technique. All petals of individual, intact orchid flowers were dipped into treatment solution and allowed to dry in Petri dishes. Treated petals were placed into individual re-sealable plastic along with about 20 adult thrips. All test arenas were held under continuous light and a temperature of about 28° C. for duration of the assay. After 3 days, the numbers of live thrips were counted on each petal. The percent mortality was recorded 72 hours after treatment.

    [1021] In this test, compounds C-2, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C-14, C-15, C-16, C-17, C-21, C-22, C-23, C-26, C-27, C-31, C-32 at 500 ppm showed at least 75% mortality in comparison with untreated controls.

    Example B3: Action on Boll Weevil (Anthonomus grandis)

    [1022] For evaluating control of boll weevil (Anthonomus grandis) the test unit consisted of 96-well-microtiter plates containing an insect diet and 5-10 A. grandis eggs.

    [1023] The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 5 μl, using a custom built micro atomizer, at two replications.

    [1024] After application, microtiter plates were incubated at about 25±1° C. and about 75±5% relative humidity for 5 days. Egg and larval mortality was then visually assessed.

    [1025] In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C-11, C-12, C-13, C14, C-15, C-16, C-17, C-19, C-20, C-21, C-22, C-23, C-24, C-25, C-26, C-27, C-28, C-29, C-30 at 800 ppm showed at least 75% mortality in comparison with untreated controls.

    Example B4: Action on Silverleaf Whitefly (Bemisia argentifolii) (Adults)

    [1026] The active compounds were formulated by a Tecan liquid handler in 100% cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppm solution was serially diluted in 100% cyclohexanone to make interim solutions. These served as stock solutions for which final dilutions were made by the Tecan in 50% acetone:50% water (v/v) into 5 or 10 ml glass vials. A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v). The vials were then inserted into an automated electrostatic sprayer equipped with an atomizing nozzle for application to plants/insects.

    [1027] Cotton plants at the cotyledon stage (one plant per pot) were sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into a plastic cup and about 10 to 12 whitefly adults (approximately 3-5 days old) were introduced. The insects were collected using an aspirator and a nontoxic Tygon® tubing connected to a barrier pipette tip. The tip, containing the collected insects, was then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. Cups were covered with a reusable screened lid. Test plants were maintained in a growth room at about 250C and about 20-40% relative humidity for 3 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment, compared to untreated control plants.

    [1028] In this test, compounds C-3, C-4, C-6, C-8, C-9, C-10, C-16, C-17, C-19, C-20, C-21, C-23, C29 at 500 ppm showed at least 75% mortality in comparison with untreated controls.

    Example B5: Action on Mediterranean Fruitfly (Ceratitis capitata)

    [1029] For evaluating control of Mediterranean fruitfly (Ceratitis capitata) the test unit consisted of microtiter plates containing an insect diet and 50-80 C. capitata eggs.

    [1030] The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 5 μl, using a custom built micro atomizer, at two replications.

    [1031] After application, microtiter plates were incubated at about 28+10C and about 80+5% relative humidity for 5 days. Egg and larval mortality was then visually assessed.

    [1032] In this test, compounds C-1, C-2, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C-13, C-14, C-15, C-16, C-17, C-19, C-20, C-21, C-22, C-23, C-24, C-25, C-26, C-27, C-28, C-29 at 800 ppm showed at least 75% mortality in comparison with untreated controls.

    Example B6: Action on Tobacco Budworm (Heliothis virescens)

    [1033] For evaluating control of tobacco budworm (Heliothis virescens) the test unit consisted of 96-well-microtiter plates containing an insect diet and 15-25 H. virescens eggs.

    [1034] The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 10 μl, using a custom built micro atomizer, at two replications.

    [1035] After application, microtiter plates were incubated at about 28±1° C. and about 80±5% relative humidity for 5 days. Egg and larval mortality was then visually assessed.

    [1036] In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C-13, C-14, C-15, C16, C-17, C-19, C-20, C-21, C-22, C-23, C-24, C-25, C-26, C-27, C-28, C-29, C-30 at 800 ppm showed at least 75% mortality in comparison with untreated controls.

    Example B7: Action on Vetch Aphid (Megoura viciae)

    [1037] For evaluating control of vetch aphid (Megoura viciae) through contact or systemic means the test unit consisted of 24-well-microtiter plates containing broad bean leaf disks.

    [1038] The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the leaf disks at 2.5 μl, using a custom built micro atomizer, at two replications.

    [1039] After application, the leaf disks were air-dried and 5-8 adult aphids placed on the leaf disks inside the microtiter plate wells. The aphids were then allowed to suck on the treated leaf disks and incubated at about 23±1° C. and about 50±5% relative humidity for 5 days. Aphid mortality and fecundity was then visually assessed.

    [1040] In this test, compounds C-6, C-10, C-21, C-28 at 800 ppm showed at least 75% mortality in comparison with untreated controls.

    Example B8: Action on Green Peach Aphid (Myzus persicae) (Mixed Life Stages)

    [1041] For evaluating control of green peach aphid (Myzus persicae) through systemic means the test unit consisted of 96-well-microtiter plates containing liquid artificial diet under an artificial membrane.

    [1042] The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were pipetted into the aphid diet, using a custom built pipetter, at two replications.

    [1043] After application, 5-8 adult aphids were placed on the artificial membrane inside the microtiter plate wells. The aphids were then allowed to suck on the treated aphid diet and incubated at about 23±1° C. and about 50±5% relative humidity for 3 days. Aphid mortality and fecundity was then visually assessed.

    [1044] In this test, compounds C-5, C-6, C-9, C-11, C-30 at 800 ppm showed at least 75% mortality in comparison with untreated controls.

    Example B9: Action on Diamond Back Moth (Plutella xylostella)

    [1045] The active compound is dissolved at the desired concentration in a mixture of 1:1 (vol:vol) distilled water:acetone. Surfactant (Kinetic® HV) is added at a rate of 0.01% (vol/vol). The test solution is prepared at the day of use.

    [1046] Leaves of cabbage were dipped in test solution and air-dried. Treated leaves were placed in petri dishes lined with moist filter paper and inoculated with ten 3.sup.rd instar larvae. Mortality was recorded 72 hours after treatment. Feeding damages were also recorded using a scale of 0-100%.

    [1047] In this test, compounds C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C-13, C-14, C-15, C-16, C-17, C-20, C-21, C-22, C-23, C-24, C-25, C-26, C-27, C-28, C-29, C-30, C-31, C-32 at 500 ppm showed at least 75% mortality in comparison with untreated controls.

    Example B10: Action on Southern Armyworm (Spodoptera eridania), 2nd Instar Larvae

    [1048] The active compounds were formulated by a Tecan liquid handler in 100% cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppm solution was serially diluted in 100% cyclohexanone to make interim solutions. These served as stock solutions for which final dilutions were made by the Tecan in 50% acetone:50% water (v/v) into 10 or 20 ml glass vials. A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v). The vials were then inserted into an automated electrostatic sprayer equipped with an atomizing nozzle for application to plants/insects.

    [1049] Lima bean plants (variety Sieva) were grown 2 plants to a pot and selected for treatment at the 1.sup.st true leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into perforated plastic bags with a zip closure. About 10 to 11 armyworm larvae were placed into the bag and the bags zipped closed. Test plants were maintained in a growth room at about 250C and about 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the bags. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants.

    [1050] In this test, compounds C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C-13, C-15, C-16, C-19, C-20, C-21, C-23, C-24, C-26, C-27, C-28, C-29 at 500 ppm showed at least 75% mortality in comparison with untreated controls.