Patent ID: 6362134
Filing Date: 2002-03-26
Classification: A01N,C07D

Abstract:
A compound of the formula I in whichR1 is a group â€”OR7, â€”NR90R91 or in which the radicals R20 independently of one another are hydrogen, C1-C4alkyl or C1-C3alkoxy; R25 is hydrogen, chlorine, methyl or methoxy; R100 is hydrogen or C1-C3alkyl; Y1 is â€”Oâ€”, â€”Sâ€” or â€”NR30; R30 is hydrogen, methyl, C1-C3alkylcarbonyl or (C1-C3alkyl)2NCO; n1 is 1, 2, 3, 4 or 5; n2 is 0, 1 or 2; and n3 is a number from 3 to 10; R7 is C1-C16alkyl, C1-C16alkyl substituted by up to 9 halogens, up to 3 NO2, CN, C1-C5alkoxy, C1-C5alkylthio, C3-C8cycloalkoxy, C3-C8cycloalkylthio, C1-C3trialkylsilyl, C3-C10alkenyloxy, C3-C5alkynyloxy, C1-C5alkylcarbonyloxy, C1-C3alkoxycarbonyl, C1-C3alkylcarbonyl, C5-C7cycloalkenyl or C5-C7cycloalkenyl substituted up to 3 times by C1-C4alkyl, or R7 is C1-C16alkyl substituted once by C3-C8cycloalkyl, C6-C12bicycloalkyl, C6-C12chlorobicycloalkyl, C6-C12bicycloalkenyl or adamantyl, or R7 is C1-C16alkyl substituted once by up to 5 times substituted or unsubstituted aryl, aryloxy, arylmethyleneoxy, arylcarbonyl, arylcarbonyloxy or a heterocyclic ring of the formula in which R98 is hydrogen, fluorine, chlorine, bromine, CN, C1-C3alkoxy, C1-C3alkoxycarbonyl, C1-C3alkoxy-C1-C3alkyl, C1- or C2halogenoalkyl, C1-C5alkyl, NO2, C3-C5alkenyl, cyclopropyl or C1- or C2halogenoalkoxy; R100 is as defined above; R24 is hydrogen or methyl; and R101 is C1-C4alkyl, C1-C4alkylcarbonyl or C1-C3-alkoxycarbonyl, or R7 is C3-C15alkenyl, C3-C15alkenyl substituted by up to 9 halogens, up to 3 C1-C3alkoxy, C3-C8cycloalkyl, C1-C3trialkylsilyl or up to 5 times substituted or unsubstituted aryl or aryloxy, or R7 is C3-C5alkynyl, C3-C12cycloalkyl, C3-C12cycloalkyl substituted by up to 9 halogens, up to 3 CN, C1-C3trialkylsilyl, &boxH;O, C1-C6alkyl, cyano-C1-C5alkyl, C1-C5alkyl-CONHâ€”C1-C5alkyl, phenyl-CONHâ€”C1-C5alkyl, C1-C5chloroalkyl, C1-C3alkoxy, C1-C3alkylthio, C1-C3alkoxycarbonyl, C1-C3alkoxycarbonyl-C1-C5alkyl, C5-C7cycloalkyl, C2-C4alkenyl, C2-C4alkynyl, benzyl or C1-C3halogenoalkyl, or R7 is C5-C7cycloalkenyl, C5-C7cycloalkenyl substituted up to 3 times by C1-C3alkyl, or R7 is C6-C12bicycloalkyl, C6-C12bicycloalkyl substituted up to 3 times by C1-C3alkyl, cyano or halogen, C6-C12bicycloalkenyl or C6-C12bicycloalkenyl substituted up to 3 times by C1-C3alkyl, or R7 is a substituted or unsubstituted non-aromatic heterocyclic ring of the formula in which R100 and R101 are as defined above, or an alicyclic ring system; R90 and R91 independently of one another are hydrogen, C1-C12alkyl, C1-C12alkyl substituted by up to 3 halogens, NO2, CN, hydroxyl, C1-C3alkoxy, C1-C3alkoxycarbonyl, C1-C3trialkylsilyl, C1-C6alkylamino, di(C1-C6alkyl)amino, C3-C7cycloalkyl, â€ƒor a heterocyclic ring of the formula in which R25 and R100 are as defined above, or C3-C10alkenyl, C3-C10alkynyl, C6-C12bicycloalkyl, C6-C12bicycioalkenyl, C3-C12cycloalkyl, C3-C12cycloalkyl substituted up to 4 times by C1-C4alkyl, C5-C7cycloalkenyl or C5-C7cycloalkenyl substituted up to 4 times by C1-C4alkyl, with the proviso that R90 and R91 are not simultaneously hydrogen; or R90 and R91, together with the nitrogen atom to which they are bonded, form a saturated heterocyclic ring which contains 2-12 carbon atoms and can contain, as further heteroatoms, a nitrogen, an oxygen or a sulfur atom and can be substituted up to 3 times by C1-C4alkyl, C1- or C2halogenoalkyl, C1- or C2hydroxyalkyl, methoxy-C1-C4alkyl, halogen, hydroxyl, CN, C1-C4alkoxy, C1-C4alkylcarbonyl, C1- or C2halogenoalkyl, â€ƒC1-C3alkoxycarbonyl, (C1-C3alkyl)2NCO, di(C1-C4alkyl)amino or &boxH;O and can additionally be bridged by 1 or 2 â€ƒgroups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused, or R90 and R91, together with the nitrogen atom to which they are bonded, form a mono- or diunsaturated heterocyclic ring which contains 5-7 carbon atoms and is substituted up to 3 times or unsubstituted by C1-C4alkyl, C1- or C2halogenoalkyl, halogen, hydroxyl, CN, amino, C1-C4alkylamino, di(C1-C4alkyl)amino, phenyl, C1-C4alkoxy or C1-C3alkoxycarbonyl and additionally bridged by 1 or 2 â€ƒgroups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused; the radicals R24 independently of one another are hydrogen or methyl; R98 is hydrogen, fluorine, chlorine, bromine, CN, C1-C3alkoxy, C1-C3alkoxycarbonyl, C1-C3alkoxy-C1-C3alkyl, C1- or C2halogenoalkyl, C1-C5alkyl, NO2, C3-C5alkenyl, cyclopropyl or C1- or C2halogenoalkoxy; R2 is halogen, C1-C10alkoxy, C1-C10alkoxy substituted up to 3 times by halogens, CN, NO2, C1-C6alkoxy, C1-C6alkylthio, C3-C6alkenyloxy, C1-C6alkoxycarbonyl, heterocyclyl of the formula in which R24, R98, R100 and R101 are as defined above, or substituted up to 5 times or unsubstituted aryl or aryloxy, C3-C10alkenyloxy, C3-C10alkenyloxy substituted up to 3 times by halogens, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, C1-C10alkylthio, C1-C10alkylthio substituted up to 3 times by halogens, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, C3-C10alkenylthio or C3-C10alkenylthio substituted up to 3 times by halogens, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, or R2 is C3-C5alkynyloxy, C3-C5alkynylthio, C3-C8cycloalkyl-Xâ€”, C6-C12bicycloalkyl-Xâ€”, heterocylyl-Xâ€”, alicyclyl-Xâ€”, aryl-Xâ€”, phthalidyl-Xâ€”, biphenyl-Xâ€” or heteroaryl-Xâ€”; X is â€”Oâ€”, â€”Sâ€”, â€”SOâ€” or â€”SO2â€”, or R2 is a group R88R89Nâ€”, R88 and R89 independently of one another are hydrogen, C1-C6alkyl, C1-C6alkyl substituted up to 3 times by halogens, CN, C1-C3alkoxy or â€ƒC3-C12cycloalkyl, C3-C10alkenyl, C3-C10alkynyl, C6-C12bicycloalkyl or C6-C12bicycloalkyl substituted up to 3 times by C1-C3alkyl; the radicals R20 independently of one another are hydrogen or C1-C4alkyl; n7 is 4 or 5; Y is â€”Oâ€”, â€”Sâ€”, â€”NHâ€” or â€”NR101â€”; R98 and R101 are as defined above; R3 is halogen, hydroxyl, C1-C10alkoxy, C1-C10alkoxy substituted up to 3 times by halogens, CN, NO2, C1-C6alkoxy, C1-C6alkylthio, C3-C6alkenyloxy, C1-C6alkoxycarbonyl, heterocyclyl of the formula in which R24, R98, R100 and R101 are as defined above, or substituted up to 5 times or unsubstituted aryl or aryloxy, C3-C10alkenyloxy, C3-C10alkenyloxy substituted up to 3 times by halogens, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, C1-C10alkylthio, C1-C10alkylthio substituted up to 3 times by halogens, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, C3-C10alkenylthio or C3-C10alkenylthio substituted up to 3 times by halogens, CN, NO2, C1-C6alkoxy, C3-C6alkenyloxy, C1-C6alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, or R3 is C3-C5alkynyloxy, C3-C5alkynylthio, C3-C8cycloalkyl-Xâ€”, C6-C12bicycloalkyl-Xâ€”, heterocyclyl-Xâ€”, alicyclyl-Xâ€”, aryl-Xâ€”, phthalidyl-Xâ€”, biphenyl-Xâ€” or heteroaryl-Xâ€”; and X is as defined above, and stereoisomers of the compounds of the formula I, excluding the compounds of formulae I1 to I7: wherein R01 is hydrogen, methyl, ethyl, n-propyl, i-butyl, tert-butyl, allyl, cyclohexyl or benzyl; R02 is ethyl, benzyl or i-butyl and R03 is ethyl, cyclohexyl, benzyl or i-butyl, or R02 and R03, together with the nitrogen atom to which they are bonded, form a piperidine ring; R04 is chlorine, methylthio, ethylthio, i-propylthio, n-butylthio, i-butylthio, phenylthio or benzylthio; R05 is ethoxy, methylthio, ethylthio or phenylthio; and R06 is chlorine or cyclohexylamino.