Patent ID: 6521610
Filing Date: 2003-02-18
Classification: A01N,A61P,C07D

Abstract:
A 4-haloalkyl-3-heterocyclylpyridine or 4-haloalkyl-5-heterocyclyl-pyrimidine of the formula I if desired in the form of its salt whereinY is halo-C1-C6alkyl; x is CH or N; m is 0 or1; Q is a 5-membered heterocyclic group in whicha) X1 = W,X2 = NRa,X3  = CRbR1orb) X1 = NRa,X2 = CRbR1,X3  = Worc) X1 = V,X2 = CRaR1,X3  = NRb ord) X1 = V,X2 = CRaR2,X3  = CRbR3ore) X1 = V,X2 = CR4R5,X3  = CR6R7orf) X1 = NRa,X2 = CRbR1,X3  = NR8;Ra and Rb together are a bond V is oxygen, sulfur or NR9; W is oxygen or sulfur; R1 is hydrogen, (C1-C20)-alkyl, (C2-C20)-alkenyl, (C2-C20)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C6-C8)-cycloalkynyl, where the six last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, â€”C(&boxH;W)R10, â€”C(&boxH;NOR10)R10, â€”C(&boxH;NNR102)R10, â€”C(&boxH;W)OR10, â€”C(&boxH;W)NR102, â€”OC(&boxH;W)R10, â€”OC(&boxH;W)OR10, â€”NR10C(&boxH;W)R10, â€”N[C(&boxH;W)R10]2, â€”NR10C(&boxH;W)OR10, â€”C(&boxH;W)NR10â€”NR102, â€”C(&boxH;W)NR10â€”NR10[C(&boxH;W)R10], â€”NR10â€”C(&boxH;W)NR102, â€”NR10â€”NR10C(&boxH;W)R10, â€”NR10â€”N[C(&boxH;W)R10]2, â€”N[(C&boxH;W)R10], â€”NR102, â€”NR10â€”NR10[(C&boxH;W)R10]2, â€”NR10â€”NR10[(C&boxH;W)WR10], â€”NR10â€”R10[(C&boxH;W)NR10]2, â€”NR10(C&boxH;NR10)R10, â€”NR10(C&boxH;NR10)NR102 â€”Oâ€”NR102, â€”Oâ€”NR10(C&boxH;W)R10, â€”SO2NR102, â€”NR10S102R10, â€”SO2OR10, â€”OSO2R10, â€”OR10, â€”NR102, â€”SR10, â€”SiR103, â€”SeR10, â€”PR102, â€”P(&boxH;W)R102, â€”SOR10, â€”SO2R10, â€”PW2R102, â€”PW3R102, aryl and heterocyclyl, the two last-mentioned radicals optionally being substituted by one or more radicals from the group (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C6-C8)cycloalkynyl, (C1-C6)-haloalkyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkynyl, halogen, â€”OR10, â€”NR102â€”SR10, â€”SiR103, â€”C(&boxH;W)R10, â€”C(&boxH;W)OR10, â€”C(&boxH;W)NR102, â€”SOR10, â€”SO2R10, nitro, cyano and hydroxyl; aryl, which is optionally substituted by one or more radicals from the group (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl and (C6C8)-cycloalkynyl, where these six abovementioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, â€”C(&boxH;W)R10, â€”C(&boxH;W)OR10, â€”C(&boxH;W)NR102, â€”OR10, â€”NR102, â€”SR10, â€”SOR10 and â€”SO2R10; halogen, cyano, nitro, â€”C(&boxH;W)R10, â€”C(&boxH;W)OR10)R10, â€”C(&boxH;NNR102)R10, â€”C(&boxH;W)OR10, â€”C(&boxH;W)NR102, â€”OC(&boxH;W)R10, â€”OC(&boxH;W)OR10, â€”NR10C(&boxH;W)R10, â€”N[C(&boxH;W)R10]2, â€”NR10C(&boxH;W)OR10, â€”OR10, â€”NR102, â€”SR10, â€”SiR103, â€”PR102, â€”SOR10, â€”SO2R10, â€”PW2R102 and â€”PW3R102, heterocyclyl, which is optionally substituted by one or more radicals from the group (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl and (C6-C8)-cycloalkynyl, where the six abovementioned radicals are optionally substituted by one or more radicals from the group cyano, nitro, halogen, â€”C(&boxH;W)R10, â€”C(&boxH;W)OR10, â€”C(&boxH;W)NR102, â€”NR10C(&boxH;W)R10, â€”N[C(&boxH;W)R10]2, â€”OC(&boxH;W)R10, â€”OC(&boxH;W)OR10, â€”OR10, â€”NR102, â€”SR10, â€”SOR10 and â€”SO2R10; halogen, cyano, nitro, â€”C(&boxH;W)R10, â€”C(&boxH;W)OR10, â€”C(&boxH;W)NR102, â€”OC(&boxH;W)R10, â€”OR10, â€”NR102, â€”SR10, â€”SOR10 and â€”SO2R10, â€”OR10, â€”NR10, â€”SR10, â€”SOR10, â€”SO2R10, â€”C(&boxH;W)R10, â€”C(&boxH;NOR10)R10, â€”C(&boxH;NNR102)R10, â€”C(&boxH;W)OR10, â€”C(&boxH;W)NR102, â€”OC(&boxH;W)R10, â€”OC(&boxH;W)OR10, â€”NR10C(&boxH;W)R10, â€”N[C(&boxH;W)R10]2, â€”NR10C(&boxH;W)OR10, â€”C(&boxH;W)NR10â€”NR102, â€”C(&boxH;W)NR10â€”NR10C(&boxH;W)R10, â€”NR10â€”C(&boxH;W)NR102, â€”NR10â€”NR10C(&boxH;W)R10, â€”NR10â€”NC(&boxH;W)R102, â€”N(C&boxH;W)R10â€”NR102, â€”NR10-NR10[(C&boxH;W)R10], â€”NR10â€”NR10[(C&boxH;W)WR10o, â€”NR10â€”NR10[(C&boxH;W)NR102], â€”NR10(C&boxH;NR10)R10, â€”NR10(C&boxH;NR10)NR102, â€”Oâ€”NR102, â€”Oâ€”NR10(C&boxH;W)R10, â€”SO2NR102, â€”NR10SO2R10, â€”SO2R10, â€”OSO2R10, â€”SC(&boxH;W)R10, â€”SC(&boxH;W)OR10, â€”SC(&boxH;W)R10, â€”PR102, â€”PW2R102, â€”PW3R102, SiR103 or halogen; R2 and R3 independently of one another have the definitions given in R1; R2 and R3 together form a 5- to 7-membered ring which may be partially or fully unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, the oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R1; R4 and R6 independently of one another have the definitions given in R1; R4 and R6 together form a 4- to 7-membered ring which may be partially or fully unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, the oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R1; R5 and R7 independently of one another are hydrogen, (C1-C20)-alkyl, (C2-C20)-alkenyl, (C2-C20)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C6-C8)-cycloalkynyl, where the six last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, â€”C(&boxH;W)R10, â€”C(&boxH;NOR10)R10, â€”C(&boxH;NNR102)R10, â€”C(&boxH;W)OR10, â€”C(&boxH;W)NR10]2, â€”OC(&boxH;W)R10, â€”OC(&boxH;W)OR10, â€”NR10C(&boxH;W)R10, â€”N[C(&boxH;W)R10]2, â€”NR10C(&boxH;W)OR10, â€”C(&boxH;W)NR10-NR102, â€”C(&boxH;W)NR10â€”NR10[C(&boxH;W)R10], â€”NR10â€”C(&boxH;W)NR10, â€”NR10â€”NR10C(&boxH;W)R10, â€”NR10â€”N[C(&boxH;W)R10]2, â€”N[(C&boxH;W)R10]-NR102, â€”NR10-NR10[(C&boxH;W)R10], â€”NR10â€”NR10[(C&boxH;W)NR10], â€”NR10Oâ€”NR10[(C&boxH;W)NR10]2, â€”N R10(C&boxH;N R10)R10, â€”NR10(C&boxH;NR10)NR102, â€”Oâ€”NR102, â€”Oâ€”NR10(C&boxH;W)R10, â€”OR10, â€”NR102, â€”SR10, â€”SiR103, â€”SeR10, â€”PR102, â€”P(&boxH;W)R102, â€”SOR10, â€”SO2R10, â€”PW2R102, â€”PW3R102, aryl and heterocyclyl, of which the two mentioned last are optionally substituted by one or more radicals from the group (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C4-C8)-cycloalkynyl, (C1-C6)-haloalkyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkynyl, halogen, â€”OR10, â€”NR102, â€”SR10, â€”SiR103, â€”C(&boxH;W)R10, â€”C(&boxH;W)OR10, â€”C(&boxH;W)NR102, â€”SOR10, â€”SO2R10, nitro, cyano and hydroxyl; aryl, which is optionally substituted by one or more radicals from the group (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl and (C6-C8)-cycloalkynyl, where these six abovementioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, â€”C(&boxH;W)R10, â€”C(&boxH;W)OR10, â€”C(&boxH;W)NR102, â€”OR10, â€”NR102, â€”SR10, â€”SOR10 and â€”SO2R10, halogen, cyano, nitro, â€”C(&boxH;W)R10, â€”C(&boxH;NOR10)R10, â€”C(&boxH;NNR102)R10, â€”C(&boxH;W)OR10, â€”C(&boxH;W)NR102, â€”OC(&boxH;W)R10, â€”OC(&boxH;W)OR10, â€”NR10C(&boxH;W)R10, â€”N[C(&boxH;W)R10]2, â€”NR10C(&boxH;W)OR10, â€”OR10, â€”NR102, â€”SR10, â€”SiR103, â€”PR102, â€”SORR10, â€”SO2R10, â€”PW2R102 and â€”PW3R102; pyridyl, which is optionally substituted by one or more radicals from the group (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl and (C6-C8)-cycloalkynyl, where the six abovementioned radicals are optionally substituted by one or more radicals from the group cyano, nitro, halogen, â€”C(&boxH;W)R10, â€”C(&boxH;W)OR10, â€”C(&boxH;W)NR102, â€”OR10, â€”NR102, â€”SR10, â€”SOR10 and â€”SO2R10; halogen, cyano, nitro, â€”C(&boxH;W)R10, â€”C(&boxH;W)OR10, â€”C(&boxH;W)NR102, â€”OC(&boxH;W)R10, â€”OR10, â€”NR102, â€”SR10, â€”SOR10 and â€”SO2R10, â€”C(&boxH;W)R10, â€”C(&boxH;NOR10)R10, â€”C(&boxH;NNR102)R10, â€”C(&boxH;W)OR10, â€”C(&boxH;W)NR102 or halogen; R4 and R5 together form a 4- to 7-membered ring which may be partially unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R10; R4 and R5 together form one of the groups &boxH;O, &boxH;S or &boxH;Nâ€”R9; R6 and R7 together form a 5- to 7-membered ring which may be partially unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R1; R6 and R7 together form one of the groups &boxH;O, &boxH;S or &boxH;Nâ€”R9; R8 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C3-C8)-cycloalkyl-(C1-C4)-alkyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenyl, (C1-C6)-alkyl-(C3-C8)-cycloalkyl, (C2-C6)-alkenyl-C3-C8)-cycloalkyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkyl, (C1-C6)-alkyl-C4-C8)-cycloalkenyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenyl, where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C6)-haloalkyloxy, (C2-C6)-haloalkenyloxy, (C2-C6)-haloalkynyloxy, (C3-C8)-cycloalkoxy, (C4-C8)-cycloalkenyloxy, (C3-C8)-halocycloalkoxy, (C4-C8)-halocycloalkenyloxy, (C3-C8)-cycloalkyl-(C1-C4)-alkoxy, (C4-C8)-cycloalkenyl-(C1-C4)-alkoxy, (C3-C8)-cycloalkyl-(C2-C4)-alkenyloxy, (C4-C8)-cycloalkenyl-(C1-C4)-alkenyloxy, (C1-C6)-alkyl-(C3-C8)-cycloalkoxy, (C2-C6)-alkenyl-(C3-C8)-cycloalkoxy, (C2-C4)-alkynyl-(C3-C8)-cycloalkoxy, (C1-C6)-alkyl-(C4-C8)-cycloalkenyloxy, (C2-C6)-alkenyl-(C4-C8)-cycloalkenyloxy, (C1-C4)-alkoxy-(C1-C6)-alkoxy, (C1-C4)-alkoxy-(C2-C6)-alkenyloxy, carbamoyl, (C1-C6)-mono- or dialkylcarbamoyl, (C1-C6)-mono- or dihaloalkylcarbamoyl, (C3-C8)-mono- or dicycloalkylcarbamoyl, (C1-C6)-alkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C6)-alkanoyloxy, (C3-C8)-cycloalkanoyloxy, (C1-C6)-haloalkoxycarbonyl, (C1-C6)-haloalkanoyloxy, (C1-C6)-alkaneamido, (C1-C6)-haloalkaneamido, (C2-C6)-alkeneamido, (C3-C8)-cycloalkaneamido, (C3-C8)-cycloalkyl-(C1-C4)-alkaneamido, (C1-C6)-alkylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C1-C6)-haloalkylthio, (C2-C6)-haloalkenylthio, (C2-C6)-haloalkynylthio, (C3-C8)-cycloalkylthio, (C4-C8)-cycloalkenylthio, (C3-C8)-halocycloalkylthio, (C4-C8)-halocycloalkenylthio, (C3-C8)-cycloalkyl-(C1-C4)-alkylthio, (C4-C8)-cycloalkenyl-(C1-C4)-alkylthio, (C3-C8)-cycloalkyl-(C2-C4)-alkenylthio, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylthio, (C1-C6)-alkyl-(C3-C8)-cycloalkylthio, (C2-C6)-alkenyl-(C3-C8)-cycloalkylthio, (C2-C6)-alkynyl-(C3-C8)-cycloalkylthio, (C1-C6)-alkyl-(C4-C8)-cycloalkenylthio, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylthio, (C1-C6)-alkylsulfinyl, (C2-C6)-alkenylsulfinyl, (C2-C6)-alkynylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C2-C6)-haloalkenylsulfinyl, (C2-C6)-haloalkynylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C4-C8)-cycloalkenylsulfinyl, (C3-C8)-halocycloalksulfinyl, (C4-C8)-halocycloalkenylsulfinyl, (C3-C8)-cycloalkyl-C1-C4)-alkylsulfinyl, (C4-C8)-cyloalkenyl-(C1-C4)-alkylsulfinyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenylsulfinyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenyIsulfinyl, (C1-C6)-alkyl-(C3-C8)-cycloalkylsulfinyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkylsulfinyl, (C2-C6)-alkynyl-C3-C8)-cycloalkylsulfinyI, (C1-C6)-alkyl-(C4-C8)-cycloalkenyIsulfinyl, (C2-CB)-alkenyl-(C4-C8)-cycloalkenylsulfinyl, (C1-C6)-alkylsulfonyl, (C2-C6)-alkenylsulfonyl, (C2-C6)-alkynylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-haloalkenylsulfonyl, (C2-C6)-haloalkynylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C4-C8)-cycloalkenylsulfonyl, (C3-C8)-halocycloalkylsulfonyl, (C4-C8)-halocycloalkenylsulfonyl, (C3-C8)-cycloalkyl-(C1-C4)-alkylsulfonyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkyl sulfonyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenylsulfonyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylsulfonyl, (C1-C6)-alkyl-(C3-C8)-cycloalkylsulfonyl, (C2-C6)-alkenyl-(C3-C8)-cycoalkylsulfonyl, (C2-C8)-cycloalkenyl-(C3-C8)-cycloalkylsulfonyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenylsulfonyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylsulfonyl, (C1-C6,)-alkylamino, (C2-C6)-alkenylamino, (C2-C6)-alkynylamino, (C1-C6)-haloalkylamino, (C2-C6)-haloalkenylamino, (C2-C6)-haloalkynylamino, (C3-C8)-cycloalkylamino, (C4-C8)-cycloalkenylamino, (C3-C8)-halocycloalkamino, (C4-C8)-halocycloalkenylamino, (C3-C8)-cycloalkyl-(C1-C4)-alkylamino, (C4-C8)-cycloalkenyl-(C1-C4)-alkylamino, (C3-C8)-cycloalkyl-(C2-C4)-alkenylamino, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylamino, (C1-C6)-alkyl-(C3-C8)-cycloalkylamino, (C2-C6)-alkenyl-(C3-C8)-cycloalkylamino, (C2-C6)-alkynyl-(C3-C8)-cycloalkylamino, (C1-C6)-alkyl-(C4-C8)-cycloalkenylamino, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylamino, (C1-C6)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, arylcarbamoyl, aroyl, aroyloxy, aryloxycarbonyl, aryl-(C1-C4)-alkoxy, aryl-(C2-C4)-alkenyloxy, aryl-(C1-C4)-alkylthio, aryl-(C2-C4)-alkenylthio, aryl-(C1-C4)-alkylamino, aryl-(C2-C4)-alkenylamino, aryl-(C1-C6)-dialkylsilyl, diaryl-(C1-C6)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl; of which the nineteen last-mentioned radicals are optionally substituted in their cyclic moiety by one or more substituents from the group halogen, cyano, nitro, amino, hydroxyl, thio, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4)-alkylamino, (C1-C4)-haloalkylamino, formyl and (C1-C4)-alkanoyl; aryl, which is optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C6)-haloalkyloxy, (C2-C6)-haloalkenyloxy, (C2-C6)-haloalkynyloxy, (C3-C8)-cycloalkoxy, (C4-C8)-cycloalkenyloxy, (C3-C8)-halocycloalkoxy, (C4-C8)-halocycloalkenyloxy, carbamoyl, (C1-C6)-mono- or dialkylcarbamoyl, (C1-C6)-alkoxycarbonyl, (Ci-C6)-alkanoyloxy, (C1-C6)-mono- or dihaloalkylcarbamoyl, (C1-C6)-haloalkoxycarbonyl, (C1-C6)-haloalkanoyloxy, (C1-C6)-alkaneamido, (C1-C6)-haloalkaneamido, (C2-C6)-alkeneamido, (C1-C6)-alkylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C1-C6)-haloalkylthio, (C2-C6)-haloalkenylthio, (C2-C6)-haloalkynylthio, (C3-C8)-cycloalkylthio, (C4-C8)-cycloalkenylthio, (C3-C8)-halocycloalkthio, (C3-C8)-halocycloalkenylthio, (C1-C6)-alkylsulfinyl, (C2-C6)-alkenylsulfinyl, (C2-C6)-alkynylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C2-C6)-haloalkenylsulfinyl, (C2-C6)-haloalkynylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C4-C8)-cycloalkenylsulfinyl, (C3-C8)-halocycloalksulfinyl, (C4-C8)-halocycloalkenylsulfinyl, (C1-C6)-alkylsulfonyl, (C2-C6)-alkenylsulfonyl, (C2-C6)-alkynylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-haloalkenylsulfonyl, (C2-C6)-haloalkynylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C4-C8)-cycloalkenylsulfonyl, (C3-C8)-halocycloalksulfonyl, (C4-C8)-halocycloalkenylsulfonyl, (C1-C6)-alkylamino, (C2-C6)-alkenylamino, (C2-C6)-alkynylamino, (C1-C6)-haloalkylamino, (C2-C6)-haloalkenylamino, (C2-C6)-haloalkynylamino, (C3-C8)-cycloalkylamino, (C4-C8)-cycloalkenylamino, (C3-C8)-halocycloalkamino and (C4-C8)-halocycloalkenylamino; â€”C(&boxH;W)R10, OR10 or NR112; R9 is (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C3-C8)-cycloalkyl-(C1-C4)-alkyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenyl, where the nine last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6) alkynyloxy and (C1-C6)-haloalkyloxy; R10 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C3-C8)-cycloalkyl-(C1-C4)-alkyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenyl, (C1-C6)-alkyl-(C3-C8)-cycloalkyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenyl, where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C6)-haloalkyloxy, (C2-C6)-haloalkenyloxy, (C2-C6)-haloalkynyloxy, (C3-C8)-cycloalkoxy, (C4-C8)-cycloalkenyloxy, (C3-C8)-halocycloalkoxy, (C4-C8)-halocycloalkenyloxy, (C3-C8)-cycloalkyl-(C1-C4)-alkoxy, (C4-C8)-cycloalkenyl-(C1-C4)-alkoxy, (C3-C8)-cycloalkyl-(C2-C4)-alkenyloxy, (C4-C8)-cycloalkenyl-(C1-C4)-alkenyloxy, (C1-C6)-alkyl-(C3-C8)-cycloalkoxy, (C2-C6)-alkenyl-(C3-C8)-cycloalkoxy, (C2-C6)-alkynyl-(C3-C8)-cycloalkoxy, (C1-C6)-alkyl-(C4-C8)-cycloalkenyloxy, (C2-C6)-alkenyl-(C4-C8)-cycloalkenyloxy, (C1-C4)-alkoxy-(C1-C6)-alkoxy, (C1-C4)-alkoxy-(C2-C6)-alkenyloxy, carbamoyl, (C1-C6)-mono- or dialkylcarbamoyl, (C1-C6)-mono- or dihaloalkylcarbamoyl, (C3-C8)-mono- or dicycloalkylcarbamoyl, (C1-C6)-alkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C6)-alkanoyloxy, (C3-C8)-cycloalkanoyloxy, (C1-C6)-haloalkoxycarbonyl, (C1-C6)-haloalkanoyloxy, (C1-C6)-alkaneamido, (C1-C6)-haloalkaneamido, (C2-C6)-alkeneamido, (C3-C8)-cycloalkaneamido, (C3-C8)-cycloalkyl-(C1-C4)-alkaneamido, (C1-C6)-alkylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C1-C6)-haloalkylthio, (C2-C6)-haloalkenylthio, (C2-C6)-haloalkynylthio, (C3-C8)-cycloalkylthio, (C4-C8)-cycloalkenylthio, (C3-C8)-halocycloalkthio, (C4-C8)-halocycloalkenylthio, (C3-C8)-cycloalkyl-(C1-C4)-alkylthio, (C4-C8)-cycloalkenyl-(C1-C4)-alkylthio, (C3-C8)-cycloalkyl-(C2-C4)-alkenylthio, (C4-C8)-cycloalkenyl-C1-C4)-alkenylthio, (C1-C6)-alkyl-(C3-C8)-cycloalkylthio, (C2-C6)-alkenyl-(C3-C8)-cycloalkylthio, (C2-C6)-alkynyl-(C3-C8)-cycloalkylthio, (C1-C6)-alkyl-(C4-C8)-cycloalkenylthio, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylthio, (C1-C6)-alkylsulfinyl, (C2-C6)-alkenylsulfinyl, (C2-C6)-alkynylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C2-C6)-haloalkenylsulfinyl, (C2-C6)-haloalkynylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C4-C8)-cycloalkenylsulfinyl, (C3-C8)-halocycloalksulfinyl, (C4-C8)-halocycloalkenylsulfinyl, (C3-C8)-cycloalkyl-(C1-C4)-alkylsulfinyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkylsulfinyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenylsulfinyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylsulfinyl1 (C1-C6)-alkyl-(C3-C8)-cycloalkylsulfinyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkylsulfinyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkylsulfinyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenyl-sulfinyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylsulfinyl, (C1-C6)-alkylsulfonyl, (C2-C6)-alkenylsulfonyl, (C2-C6)-alkynylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-haloalkenylsulfonyl, (C2-C6)-haloalkynylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C4-C8)-cycloalkenylsulfonyl, (C3-C8)-halocycloalksulfonyl, (C4-C8)-halocycloalkenylsulfonyl, (C3-C8)-cycloalkyl-(C1-C4)-alkylsulfonyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkylsulfonyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenylsulfonyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylsulfonyl, (C1-C6)-alkyl-(C3-C8)-cycloalkylsulfonyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkylsulfonyl, (C2-C6)-alkynyl-C3-C8)-cycloalkylsulfonyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenylsulfonyl, (C2-C6)-alkenyl-(C4-C8)cycloalkenylsulfonyl, (C1-C6)-alkylamino, (C2-C6)-alkenylamino, (C2-C6)-alkynylamino, (C1-C6)-haloalkylamino, (C2-C6)-haloalkenylamino, (C2-C6)-haloalkynylamino, (C3-C8)-cycloalkylamino, (C4-C8)-cycloalkenylamino, (C3-C8)-halocycloalkamino, (C4-C8)-halocycloalkenylamino, (C3-C8)-cycloalkyl-(C1-C4)-alkylamino, (C4-C8)-cycloalkenyl-(C1-C4)-alkylamino, (C3-C8)-cycloalkyl-(C2-C4)-alkenylamino, (C4-C8)cycloalkenyl-(C1-C4)-alkenylamino, (C1-C6)-alkyl-(C3-C8)-cycloalkylamino, (C2-C6)-alkenyl-(C3-C8)-cycloalkylamino, (C2-C6)-alkynyl-(C3-C8)-cycloalkylamino, (C1-C6)-alkyl-(C4-C8)-cycloalkenylamino, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylamino, (C1-C6)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, aryl-(C1-C4)-alkoxy, aryl-(C2-C4)-alkenyloxy, aryl-(C1-C4)-alkylthio, aryl-(C2-C4)-alkenylthio, aryl-(C1-C4)-alkylamino, aryl-(C2-C4)-alkenylamino, aryl-(C1-C6)-dialkylsilyl, diaryl-(C1-C6)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocycyl, where the cyclic moiety of the fourteen last-mentioned radicals is optionally substituted by one or more radicals from the group halogen, cyano, nitro, amino, hydroxyl, thio, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C3-C8)-cycloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4)-alkylamino, (C1-C4)-haloalkylamino, formyl and (C1-C4)-alkanoyl; aryl, 5- or 6-membered heteroaromatic, where the two last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C6)-haloalkyloxy, (C2-C6)-haloalkenyloxy, (C2-C6)-haloalkynyloxy, (C3-C8)-cycloalkoxy, (C4-C8)-cycloalkenyloxy, (C3-C8)-halocycloalkoxy, (C4-C8)-halocycloalkenyloxy, carbamoyl, (C1-C6)-mono- or dialkylcarbamoyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkanoyloxy, (C1-C6)-mono- or dihaloalkylcarbamoyl, (C1-C6)-haloalkoxycarbonyl, (C1-C6)-haloalkanoyloxy, (C1-C6)-alkaneamido, (C1-C6)-haloalkaneamido, (C2-C6)-alkeneamido, (C1-C6)-alkylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C1-C6)-haloalkylthio, (C2-C6)-haloalkenylthio, (C2-C6)-haloalkynylthio, (C3-C8)-cycloalkylthio, (C4-C8)-cycloalkenylthio, (C3-C8)-halocycloalkthio, (C4-C8)-halocycloalkenylthio, (C1-C6)-alkylsulfinyl, (C2-C6)-alkenylsulfinyl, (C2-C6)-alkynylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C2-C6)-haloalkenylsulfinyl, (C2-C6)-haloalkynylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C4-C8)-cycloalkenylsulfinyl, (C3-C8)-halocycloalksulfinyl, (C4-C8)-halocycloalkenylsulfinyl, (C1-C6)-alkylsulfonyl, (C2-C6)-alkenylsulfonyl, (C2-C6)-alkynylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-haloalkenylsulfonyl, (C2-C6)-haloalkynylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C4-C8)-cycloalkenylsulfonyl, (C3-C8)-halocycloalkylsulfonyl, (C4-C8)-halocycloalkenylsulfonyl, (C1-C6)-alkylamino, (C2-C6)-alkenylamino, (C2-C6)-alkynylamino, (C1-C6)-haloalkylamino, (C2-C6)-haloalkenylamino, (C1-C6)-haloalkynylamino, (C3-C8)-cycloalkylamino, (C4-C8)-cycloalkenylamino, (C3-C8)-halocycloalkamino and (C4-C8)-halocycloalkenylamino; R11 is (C1-C10)-alkyl, haloalkyl, aryl, which is optionally substituted by one or more radicals from the group halogen, cyano, nitro, (C1-C4)-alkoxy, (C1-C4)-alkyl, amino, (C1-C4)-monoalkylamino and (C1-C4)-dialkylamino; NR102, OR10 or SR10 with the proviso that the compounds listed below are not included:3-(2-chlorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole 3-(2,6-difluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1 ,2,4-triazole 3-(2chloro4-fluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole 3-(3,5-dichlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(4-trifluoromethyl-3-pyridyl)-3-phenyl-1,2,4-oxadiazole 3-(4-trifluoromethyl-3-pyridyl)-5-phenyl-1,2,4-oxadiazole 5-(2-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(3-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(4-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(2-fluorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(4-fluorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(2,4-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(3,4-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(3,5ichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-xadiazole 5-(2,6-dichloro4-pynidyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(3,5-bistrifluoromethylp heny l)-3- (4-trifluoromethyl-3-pyridyl)-1,2,4oxadiazo le 2-(2-chloro phenyl)-5-( 4-trifluoromethyl -3-pyridyl)-1,3,4-xadiazole 2-(3chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole 2-(4-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole 2-(2-trfluoromethoxyphenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazo le 2-(4-trifluoromethoxyphenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole 2-(4-trifluoromethyl-3-pyridyl)-5-phenyl-1,3,4-oxadiazole 2-(4-trifluoromethyl-3-pyridyl)4-methylthiazolecarbohydrazide ethyl 2-(4-trifluoromethyl-3-pyridyl)-4-methylthiazolecarboxylate N-(4-chlorophenyl)-carbonyl-Nâ€²-[2-(4-trifluoromethyl-3-pyridyl)4-methyl-5-thiazolyl]carbonylhydrazine 2-(4-trifluoromethyl-3-pyridyl)4-thiazolecarbohydrazide 4-(4-chlorophenyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole 4-(4-yanophenyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole N-(4-trifluoromethylphenyl)carbonylâ€”Nâ€²-[2-(4-trifluoromethyl-3-pyridyl)4-thiazolyl]carbonylhydrazine 2-(2-(4-trifluoromethyl-3-pyridyl)thiazolyi)-5chloro-3-methylbenzo[b]thiophene 2-(4-chlorophenylmethylthio)-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole 2-(4-chlorophenylcarbonylmethylthio)-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole and 2-ethoxycarbonylmethylthio-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole.