Patent ID: 6410482
Filing Date: 2002-06-25
Classification: A01N,C07C,C07D

Abstract:
A compound of the formula (I) or a salt thereof whereinA is a bridge of the formulae A1-A9m is 0 or 1, U is CH2, O or NH or (C1-C3-alkyl)N, B is a group of the formula B1 to B5, R is hydrogen, C1-C5-alkyl, C1-C5-haloalkyl, C2-C5-alkenyl, C2-C5-haloalkenyl, C2-C5-alkynyl or C2-C5-haloalkynyl, R1 is H, CN, halogen, azide, NO2, OH, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy, C1-C8-alkylthio, C2-C8-alkenylthio, C2-C8-alkynylthio, C1-C8-alkylsulfinyl, C2-C8-alkenylsulfinyl, C2-C8-alkynylsulfinyl, C1-C8-alkylsulfonyl, C2-C8-alkenylsulfonyl, C2-C8-alkynylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C8-cycloalkylthio, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C5-C8-cycloalkenyl, C5-C8-cycloalkenyloxy, C5-C8-cycloalkenylthio, C5-C8-cycloalkenylsulfinyl or C5-C8-cycloalkenylsulfonyl, each of the last 25 radicals being unsubstituted or substituted by one or more radicals from the group consisting of halogen, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, OH, CN, NO2, oxo, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, (C1-C4-alkoxy)carbonyl, (C1-C4-haloalkoxy)-carbonyl, NR32R33 and, in the case of cyclic radicals, also C1-C4-alkyl and C1-C4-haloalkyl, or is COR24, CSR25, C(&boxH;Nk26)R27, NR28R29, SO2NR30 R31 or a heterocycle which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, C1-C4-alkyl, OH, CN, NO2, CHO, NH2, mono- and di-(C1-C4-alkyl)amino, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl and oxo, or is aryl, hetaryl, aryl-C1-C3-alkyl or hetaryl-C1-C3-alkyl, the aryl or hetaryl moiety of each of the last 4 radicals being unsubstituted or substituted by one or more radicals from the group consisting of halogen, OH, CN, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, (C1-C4-alkoxy)carbonyl, (C1-C4-haloalkoxy)-carbonyl, mono- and di(C1-C4-alkyl)amino, CHO, NH2, CONH2, mono- and di-(C1-C4-alkyl)-aminocarbonyl, R2 is hydrogen, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy, C1-C8-alkylthio, C2-C8-alkenylthio, C2-C8-alkynylthio, C1-C8-alkylsulfonyl, C2-C8-alkenylsulfonyl, C2-C8-alkynylsulfonyl, C3-C8-cycloalkyl, C5-C8-cycloalkenyl, C5-C8-cycloalkoxy, C5-C8-cycloalkenyloxy, C3-C8-cycloalkylthio, C5-C8-cycloalkenylthio, C3-C8-cycloalkylsulfonyl or C5-C8-cycloalkenylsulfonyl, each of the last 20 radicals being unsubstituted or substituted by one or more radicals from the group consisting of halogen, C1-C4-alkoxy and C1-C4-haloalkoxy and, in the case of cyclic radicals, also C1-C4-alkyl and C1-C4-haloalkyl, or is halogen, CN, NH2, mono- or di-(C1-C4-alkyl)amino, R3, R5, R7, R9, R11, R13, and R14 are each a radical from the group of the radicals as defined for R1, R4, R6, R8, R10 and R12 are each a radical from the group of the radicals as defined for R2, R15 is hydrogen, C1-C8-alkyl, C3-C8-cycloalkyl, C1-C8-haloalkyl, C3-C8-halocycloalkyl, or aryl which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl; C1-C4-alkoxy and C1-C4-haloalkoxy, R16 is NH2, hydrogen, aryl or hetaryl, each of the last two radicals being unsubstituted or substituted, or C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy, C1-C8-alkylthio, C2-C8-alkenylthio, C2-C8-alkynylthio, C3-C8-cycloalkyl, C5-C8-cycloalkenyl, C3-C6-cycloalkoxy, C5-C8-cycloalkenyloxy, C3-C8-cycloalkylthio, C5-C8-cycloalkenylthio, mono-or di-(C1-C6)alkylamino, each of the last 17 radicals being unsubstituted or substituted, or benzyl, CN, (C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)carbonyl, benzyloxycarbonyl or phenylcarbonyl, R17 is OH, NH2, hydrogen, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy, (C1-C8-alkyl)carbonyl, (C1-C8-alkoxy)carbonyl, benzoyl, benzyloxycarbonyl, (C1-C8)-alkylsulfonyl, arylsulfonyl, C3-C8-cycloalkyl, C5-C8-cycloalkenyl, C3-C8-cycloalkoxy, C5-C8-cycloalkenyloxy, C3-C8-cycloalkylcarbonyl, C3-C8-cycloalkoxycarbonyl, C3-C8-cyclo-alkylsulfonyl, mono- or di-(C1-C8-alkyl)amino, each of the last 21 radicals being unsubstituted or substituted by one or more radicals from the group consisting of halogen, C1-C4-alkoxy, C1-C4-haloalkoxy, CN, NO2, OH, NH2, mono- and di-(C1-C3-alkyl)amino, C1-C4-alkylthio and C1-C4-haloalkylthio and, in the case of cyclic radicals, also C1-C4-alkyl and C1-C4-haloalkyl, or is aryl or hetaryl, each of the last 2 radicals being unsubstituted or substituted by one or more radicals from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, CN and NO2, or the part of the formula from the group of the abovementioned formula B1 (see definition of B) as a whole forms a heterocyclic ring having an imino function, wherein said rings are selected from a ring of the formulae D1 to D15wherein said rings D1 to D15 are unsubstituted or substituted by one or more radicals from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, OH, NH2, CN, NO2, mono- and di-(C1-C4-alkyl)amino.R18 is hydrogen, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkylsulfonyl, (C1-C8-alkyl)carbonyl, (C1-C8-alkoxy)carbonyl, C1-5-alkoxy, C3-C8-cycloalkyl, C5-C8-cycloalkenyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylcarbonyl, C3-C8-cycloalkoxycarbonyl or C3-C8-cycloalkoxy, each of the last 13 radicals being unsubstituted or substituted by one or more radicals from the group consisting of halogen, C1-C3-alkoxy, C1-C3-haloalkoxy and, in the case of cyclic radicals, also C1-C4-alkyl and C1-C4-haloalkyl, or is CHO, NH2, OH, mono- or di-(C1-C4-alkyl)amino, R19 is a radical selected from the group of the radicals as defined for R17 and R20 is hydrogen, C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, C3-C8-cycloalkenyl or C2-C6-alkynyl or NR19R20 is a heterocyclic ring, having 3 to 6 ring atoms and, in addition to the 1-nitrogen atom, may optionally contain one further hetero ring atom selected from the group consisting of N, O, and S which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, OH, NH2, NO2, CN, mono- and di-(C1-C5-alkyl)amino, R21 is a radical from the group of the radicals possible for R16, R22 is hydrogen, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkoxy, C1-C8-alkylthio, C3-C8-cycloalkoxy, C3-C8-cycloalkylthio, C3-C8-cycloalkyl, C5-C8-cycloalkenyl, mono- or di-(C1-C8-alkyl)amino, each of the last 11 radicals being unsubstituted or substituted by one or more radicals from the group consisting of CN, halogen, C1-C4-alkoxy, C1-C4-haloalkoxy and, in the case of cyclic radicals, also C1-C4-alkyl and C1-C4-haloalkyl, or is aryl or hetaryl, R23 is C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C3-C8-cycloalkyl, C5-C8-cycloalkenyl, heterocyclyl, aryl or benzyl, each of the last 8 radicals being unsubstituted or substituted by one or more radicals from the group consisting of halogen, C1-C4-alkoxy, C1-C4-haloalkoxy, CN and NO2 and, in the case of cyclic radicals, also C1-C4-alkyl and C1-C4-haloalkyl, R24 is hydrogen, OH, NH2, aryl or a heterocycle, each of the last two radicals being unsubstituted or substituted, or is C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy, C1-C8-alkylthio, C2-C8-alkenylthio, C2-C8-alkynylthio, benzyl, aryloxy, benzyloxy, C3-C8-cycloalkyl, C5-C8-cycloalkenyl, C3-C8-cycloalkoxy, C5-C8-cycloalkenyloxy, C5-C8-cycloalkylthio or C5-C8-cycloalkenylthio, mono- or di-(C1-C8-alkyl)amino, each of the last 20 radicals being unsubstituted or substituted by one or more radicals from the group consisting of halogen, C1-C4-alkoxy, C1-C4-haloalkoxy, OH, NH2, mono- and di-(C1-C4-alkyl)amino, CN and NO2 and, in the case of cyclic radicals, also C1-C4-alkyl and C1-C4-haloalkyl, R25 is a radical from the group of the radicals possible for R24, R26 is hydrogen, OH, NH2, CN, C1-C8-alkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkylsulfonyl, C2-C8-alkenylsulfonyl, C2-C8-alkynylsulfonyl, C3-C8-cycloalkoxy, C5-C8-cycloalkenyloxy, C3-C8-cycloalkyl, C5-C8-cycloalkenyl, C3-C8-cycloalkylsulfonyl, C5-C8-cycloalkenylsulfonyl, arylsulfonyl or aryl or a heterocycle or benzyl, (C1-C8-alkoxy)carbonyl, (C1-C8-alkyl)carbonyl, phenoxycarbonyl, benzylcarbonyl or heterocyclylcarbonyl, each of the last 24 radicals being unsubstituted or substituted, R27 is a radical from the group of the radicals possible for R24, excluding OH, R28 is H, OH, CHO, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy, C1-C8-alkylsulfonyl, C2-C8-alkenylsulfonyl, C2-C8-alkynylsulfonyl, (C1-C8-alkyl)carbonyl, (C2-C8-alkenyl)carbonyl, (C2-C8-alkynyl)-carbonyl, (C1-C8-alkoxy)carbonyl, (C2-C8-alkenyloxy)carbonyl, (C2-C8-alkynyloxy)carbonyl, mono- or di-(C1-C8-alkyl)-aminocarbonyl, C3-C8-cycloalkyl, C5-C8-cycloalkenyl, C3-C8-cycloalkoxy, C5-C8-cycloalkenyloxy, C3-C9-cycloalkylsulfonyl, C5-C8-cycloalkenylsulfonyl, C3-C8-cycloalkoxycarbonyl, C5-C8-cycloalkenyloxycarbonyl, benzoyl, benzyl, benzylcarbonyl, benzyloxycarbonyl, aryl or a heterocycle, each of the last 31 radicals being unsubstituted or substituted, or is SO2NH2 or CONH2, R29 is a radical from the group of the radicals possible for R28, excluding OH, R30 is a radical from the group of the radicals possible for R19, R31 is a radical from the group of the radicals possible for R20, or NR30R31 as a whole forms a heterocyclic ring as defined for NR19R20, R32 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, CHO, C1-C4-alkylsulfonyl, C2-C4-alkenyl, C2-C4-alkynyl, C2-C4-haloalkenyl, C1-C4-haloalkyl, C2-C4-haloalkynyl, C1-C4-haloalkylsulfonyl, (C1-C4-alkyl)carbonyl, (C1-C4-alkoxy)carbonyl, (C1-C4-haloalkyl)carbonyl or (C1-C4-haloalkoxy)carbonyl, R33 is a radical from the group of the radicals possible for R32 or NR32R33 as a whole forms a heterocyclic ring as defined for NR19R20. and wherein, unless otherwise defined, aryl is a mono-, bi- or polyaromatic ring system which has 6 to 12 carbon atoms which is substituted or unsubstituted, hetaryl is a mono-, bi- or polyaromatic ring system which has 6 to 12 carbon atoms wherein one of said carbon atoms is replaced by a heteroatom selected from the group consisting of N, O, and sulfur or is heteroring selected from the group consisting of pyrimidine, pyridazine, pyrazine, thiazole, oxazole, pyrazole, imidazole, quinoline, and benzoxazole which are substituted or unsubstituted; heterocyclyl or heterocyclic ring is saturated, unsaturated or aromatic ring containing 3 to 8 carbon atoms wherein one of the carbon atoms is replaced by a hetero atom selected from the group consisting of N, O, and S, or is a heteroring selected from the group consisting of piperdine, piperazine, dioxolane, morpholine, pyrimidine, pyridazine, thiazole, oxazole, pyrazole, imidazole, quinoline, and benzoxazole, which are substituted or unsubstituted; and said substituents on the aryl, hetaryl, heterocyclyl or heterocyclic ring are one or more radicals selected from the group consisting of halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkenyl, aryl, heterocyclyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, OH, NH, NH2, NO2, CN, Nâ‰¡N, C1-C4-alkylthio, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, formyl, carbamoyl, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, mono-(C1-C4)alkylamino carbonyl, di(C1-C4-alkyl)carbonyl, acylamino, C1-C4-alkylsulfinyl, halo-(C1-C4)-alkylsulfinyl, C1-C4-alkylsulfonyl, halo(C1-C4-alkyl)sulfonyl, C2-C4-alkenyloxy, and C2-C4-alkynyloxy.