Novel 5-substituted imidazolylmethyl derivatives

Imidazole derivative of formula (I)

• wherein
• R1 represents a structure of formula (R1—I),
• wherein
• R1a represents hydrogen, C1-C8-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, [tri(C1-C8-alkyl)silyl]phenyl-C2-C8-alkynyl, optionally halogen-, cyano-, C1-C4-alkoxy-, C1-C4-haloalkoxy-, C1-C4-alkylthio- or C1-C4-haloalkylthio-substituted phenyl-C2-C8-alkynyl, optionally halogen-, cyano-, C1-C4-alkoxy-, C1-C4-haloalkoxy-, C1-C4-alkylthio- or C1-C4-haloalkylthio-substituted C3-C7-cycloalkyl, optionally halogen-, cyano-, C1-C4-haloalkyl-, C1-C4-alkoxy-, C1-C4-alkylthio- or C1-C4-haloalkylthio-substituted bicycloalkyl, optionally halogen-, cyano-, C1-C4-alkoxy-, C1-C4-haloalkoxy-, C1-C4-alkylthio- or C1-C4-haloalkylthio-substituted C3-C8-cycloalkylalkyl, optionally cyano-, C1-C4-alkoxy-, C1-C4-haloalkoxy-, C1-C4-alkylthio- or C1-C4-haloalkylthio-substituted C3-C7-halocycloalkyl-C1-C4-alkyl, optionally cyano-, C1-C4-alkoxy-, C1-C4-haloalkoxy-, C1-C4-alkylthio- or C1-C4-haloalkylthio-substituted C3-C7-halocycloalkyl-C1-C4-haloalkyl, optionally cyano-, C1-C4-alkyl-, C1-C4-haloalkyl-, C1-C4-alkoxy-, C1-C4-haloalkoxy-, C1-C4-alkylthio- or C1-C4-haloalkylthio-substituted C3-C7-cycloalkyl-C1-C4-haloalkyl, optionally halogen-, cyano-, C1-C4-alkyl-, C1-C4-haloalkyl-, C1-C4-alkoxy-, C1-C4-haloalkoxy-, C1-C4-alkylthio- or C1-C4-haloalkylthio-substituted C3-C7-cycloalkyl-C3-C7-cycloalkyl, optionally halogen-, cyano-, C1-C4-alkyl-, C1-C4-haloalkyl-, C1-C4-alkoxy-, C1-C4-haloalkoxy-, C1-C4-alkylthio- or C1-C4-haloalkylthio-substituted C3-C7-cycloalkenyl, optionally halogen-, cyano-, C1-C4-alkyl-, C1-C4-haloalkyl-, C1-C4-alkoxy-, C1-C4-haloalkoxy-, C1-C4-alkylthio- or C1-C4-haloalkylthio-substituted tri(C1-C8-alkyl)silyl-C1-C4-alkyl, optionally halogen-, cyano-, C1-C4-haloalkyl-, C1-C4-alkoxy-, C1-C4-haloalkoxy-, C1-C4-alkylthio- or C1-C4-haloalkylthio-substituted tri(C1-C8-alkyl)silyl-C3-C7-cycloalkyl
• naphthyl, 5-membered heteroaryl, benzofuranyl, or a substituent of formula Q1,
• wherein the naphthyl, 5-membered heteroaryl, and benzofuranyl, is non-substituted or substituted by one or more group(s) selected from halogen, cyano, sulfanyl, pentafluoro-λ6-sulfanyl, C1-C8-alkyl, C1-C8-haloalkyl, C1-C8-cyanoalkyl, C1-C8-alkyloxy, C1-C8-haloalkyloxy, tri(C1-C8-alkyl)silyl, tri(C1-C8-alkyl)silyl-C1-C8-alkyl, C3-C7-cycloalkyl, C3-C7-halocycloalkyl, C3-C7-cycloalkenyl, C3-C7-halocycloalkenyl, C4-C10-cycloalkylalkyl, C4-C10-halocycloalkylalkyl, C6-C12-cycloalkylcycloalkyl, C1-C8-alkyl-C3-C7-cycloalkyl, C1-C8-alkoxy-C3-C7-cycloalkyl, tri(C1-C8-alkyl)silyl-C3-C7-cycloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, C3-C8-alkynyloxy, C3-C8-haloalkynyloxy, C1-C8-cyanoalkoxy, C4-C8-cycloalkylalkoxy, C3-C6-cycloalkoxy, C1-C8-alkylsulfanyl, C1-C8-haloalkylsulfanyl, C1-C8-alkylsulfinyl, C1-C8-haloalkylsulfinyl, C1-C8-alkylsulfonyl, C1-C8-haloalkylsulfonyl, C1-C8-alkylsulfonyloxy, C1-C8-haloalkylsulfonyloxy, C1-C8-alkoxyalkyl, C1-C8-alkylthioalkyl, C1-C8-alkoxyalkoxyalkyl, C1-C8-haloalkoxyalkyl, benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, benzyloxy, phenoxy, 4-halogen-substituted phenoxy, 4-(C1-C8-haloalkyl)-substituted phenoxy, benzylsulfanyl, phenylsulfanyl, or 6-membered heteroaryloxy, which is non-substituted or substituted by one or more group(s) selected from halogen and C1-C8-haloalkyl;
• and
• wherein Q1 represents a 6-membered aromatic cycle of formula (Q1-I)
• wherein
• U1 represents CX1 or N;
• U2 represents CX2 or N;
• U3 represents CX3 or N;
• U4 represents CX4 or N;
• U5 represents CX5 or N;
• wherein X1, X2, X3, X4, and X5 independently from each other represent hydrogen, halogen, nitro, cyano, sulfanyl, pentafluoro-λ6-sulfanyl, C1-C8-alkyl, C3-C8-cycloalkyl, C3-C7-halocycloalkyl having 1 to 5 halogen atoms, C1-C8-haloalkyl-C3-C7-cycloalkyl, C3-C7-cycloalkenyl, C1-C8-haloalkyl having 1 to 5 halogen atoms, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkoxy, C1-C8-haloalkoxy having 1 to 5 halogen atoms, C1-C8-alkylsulfenyl, C2-C8-alkenyloxy, C3-C8-alkynyloxy, C3-C6-cycloalkoxy, C1-C8-alkylsulfinyl, C1-C8-alkylsulfonyl, tri(C1-C8-alkyl)-silyloxy, tri(C1-C8-alkyl)-silyl, aryl, aryloxy, arylsulfenyl, heteroaryl, heteroaryloxy,
• wherein the aryl, aryloxy, arylsulfenyl, heteroaryl, heteroaryloxy is non-substituted or substituted by one or more group(s) selected from halogen, cyano, sulfanyl, pentafluoro-λ6-sulfanyl, C1-C8-alkyl, C1-C8-haloalkyl, C1-C8-cyanoalkyl, C1-C8-alkyloxy, C1-C8-haloalkyloxy, tri(C1-C8-alkyl)silyl, tri(C1-C8-alkyl)silyl-C1-C8-alkyl, C3-C7-cycloalkyl, C3-C7-halocycloalkyl, C3-C7-cycloalkenyl, C3-C7-halocycloalkenyl, C4-C10-cycloalkylalkyl, C4-C10-halocycloalkylalkyl, C6-C12-cycloalkylcycloalkyl, C1-C8-alkyl-C3-C7-cycloalkyl, C1-C8-alkoxy-C3-C7-cycloalkyl, tri(C1-C8-alkyl)silyl-C3-C7-cycloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, C3-C8-alkynyloxy, C3-C8-haloalkynyloxy, C1-C8-cyanoalkoxy, C4-C8-cycloalkylalkoxy, C3-C6-cycloalkoxy, C1-C8-alkylsulfanyl, C1-C8-haloalkylsulfanyl, C1-C8-alkylsulfinyl, C1-C8-haloalkylsulfinyl, C1-C8-alkylsulfonyl, C1-C8-haloalkylsulfonyl, C1-C8-alkylsulfonyloxy, C1-C8-haloalkylsulfonyloxy, C1-C8-alkoxyalkyl, C1-C8-alkylthioalkyl, C1-C8-alkoxyalkoxyalkyl, C1-C8-haloalkoxyalkyl, benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, 6-membered heteroaryloxy, benzyloxy, phenyloxy, benzylsulfanyl, or phenylsulfanyl,
• wherein the benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, 6-membered heteroaryloxy, benzyloxy, phenyloxy, benzylsulfanyl, or phenylsulfanyl is non-substituted or substituted by one or more group(s) selected from halogen, CN, nitro, C1-C8-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or pentafluoro-λ6-sulfanyl;
• and wherein at most two of U1, U2, U3, U4 and U5 can represent N;
• or
• U1 and U2 or U2 and U3 or U3 and U4 form together an additional saturated or unsaturated 4 to 6-membered halogen- or C1-C8-alkyl-substituted or non-substituted ring;
• R4a and R5a represent independently from each other hydrogen, fluorine, C1-C8-alkyl, C1-C8-haloalkyl or C1-C8-alkyloxy;
• or
• R4a and R5a form together with the carbon atom to which they are attached an optionally halogen-, C1-C4-alkyl-, C1-C4-haloalkyl-, C1-C4-alkoxy-, C1-C4-haloalkoxy-, C1-C4-alkylthio- or C1-C4-haloalkylthio-substituted C3-C7-cycloalkyl ring;
• n represents 0 or 1;
• R2 represents hydrogen, cyano or —OR2a,
• wherein
• R2a represents hydrogen, C1-C8-alkyl, C1-C3-cyanoalkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C8-alkenyl, C3-C8-alkynyl, C3-C7-cycloalkyl-C1-C3-alkyl, —Si(R3a)(R3b)(R3c), —P(O)(OH)2, —CH2—O—P(O)(OH)2, CH2—C(O)—O—C1-C8-alkyl, C(O)—C1-C8-alkyl, C(O)—C3-C7-cyclo alkyl, C(O)NH—C1-C8-alkyl, —C(O)N-di-C1-C8-alkyl, C(O)O—C1-C8-alkyl,
• wherein the C(O)—C1-C8-alkyl, C(O)—C3-C7-cycloalkyl, C(O)NH—C1-C8-alkyl, C(O)N-di-C1-C8-alkyl or C(O)O—C1-C8-alkyl is non-substituted or substituted by one or more group(s) selected from halogen or C1-C8-alkoxy;
• wherein
• R3a, R3b, R3c represent independently from each other phenyl or C1-C8-alkyl;
• R3 represents halogen, hydroxyl, cyano, isocyano, amino, sulfanyl, pentafluoro-λ6-sulfanyl, carboxaldehyde, hydroxycarbonyl, C2-C8-alkyl, C1-C8-haloalkyl, C1-C8-cyanoalkyl, C1-C8-alkyloxy, C1-C8-haloalkyloxy, tri(C1-C8-alkyl)silyl, tri(C1-C8-alkyl)silyl-C1-C8-alkyl, C3-C7-cycloalkyl, C3-C7-halocycloalkyl, C3-C7-cycloalkenyl, C3-C7-halocycloalkenyl, C4-C10-cycloalkylalkyl, C4-C10-halocycloalkylalkyl, C6-C12-cycloalkylcycloalkyl, C1-C8-alkyl-C3-C7-cycloalkyl, C1-C8-alkoxy-C3-C7-cycloalkyl, tri(C1-C8-alkyl)silyl-C3-C7-cycloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, C3-C8-alkynyloxy, C3-C8-haloalkynyloxy, C1-C8-alkylamino, C1-C8-haloalkylamino, C1-C8-cyanoalkoxy, C4-C8-cycloalkylalkoxy, C3-C6-cycloalkoxy, C1-C8-alkylsulfanyl, C1-C8-haloalkylsulfanyl, C1-C8-alkylcarbonyl, C1-C8-haloalkylcarbonyl, arylcarbonyl, aryl-C1-C6-alkylcarbonyl, C3-C8-cycloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, carbamoyl, C1-C8-alkylcarbamoyl, di-C1-C8-alkylcarbamoyl, N—C1-C8-alkyloxycarbamoyl, C1-C8-alkoxycarbamoyl, N—C1-C8-alkyl-C1-C8-alkoxycarbamoyl, aminothiocarbonyl, C1-C8-alkoxycarbonyl, C1-C8-haloalkoxycarbonyl, C3-C8-cycloalkoxycarbonyl, C2-C8-alkoxyalkylcarbonyl, C2-C8-haloalkoxyalkylcarbonyl, C3-C10-cycloalkoxyalkylcarbonyl, C1-C8-alkylaminocarbonyl, di-C1-C8-alkylaminocarbonyl, C3-C8-cycloalkylaminocarbonyl, C1-C8-alkylcarbonyloxy, C1-C8-haloalkylcarbonyloxy, C3-C8-cycloalkylcarbonyloxy, C1-C8-alkylcarbonylamino, C1-C8-halo alkylcarbonylamino, C1-C8-alkylaminocarbonyloxy, di-C1-C8-alkylaminocarbonyloxy, C1-C8-alkyloxycarbonyloxy, C1-C8-alkylsulfinyl, C1-C8-haloalkylsulfinyl, C1-C8-alkylsulfonyl, C1-C8-haloalkylsulfonyl, C1-C8-alkylsulfonyloxy, C1-C8-haloalkylsulfonyloxy, C1-C8-alkylaminosulfamoyl, di-C1-C8-alkylaminosulfamoyl, (C1-C8-alkoxyimino)-C1-C8-alkyl, (C3-C7-cycloalkoxyimino)-C1-C8-alkyl, hydroxyimino-C1-C8-alkyl, (C1-C8-alkoxyimino)-C3-C7-cyclo alkyl, hydroxyimino-C3-C7-cycloalkyl, (C1-C8-alkylimino)-oxy, (C1-C8-alkylimino)-oxy-C1-C8-alkyl, (C3-C7-cycloalkylimino)-oxy-C1-C8-alkyl, (C1-C6-alkylimino)-oxy-C3-C7-cyclo alkyl, (C1-C8-alkenyloxyimino)-C1-C8-alkyl, (C1-C8-alkynyloxyimino)-C1-C8-alkyl, (benzyloxyimino)-C1-C8-alkyl, C1-C8-alkoxyalkyl, C1-C8-alkylthioalkyl, C1-C8-alkoxyalkoxyalkyl, C1-C8-haloalkoxyalkyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, benzyloxy, phenyloxy, benzylsulfanyl, benzylamino, phenylsulfanyl, or phenylamino, wherein the phenyl, 5-membered heteroaryl, 6-membered heteroaryl, benzyloxy or phenyloxy is non-substituted or substituted by one or more group(s) selected from halogen, hydroxyl, cyano, isocyano, amino, sulfanyl, pentafluoro-λ6-sulfanyl, carboxaldehyde, hydroxycarbonyl, C1-C8-alkyl, C1-C8-haloalkyl, C1-C8-cyanoalkyl, C1-C8-alkyloxy, C1-C8-haloalkyloxy, tri(C1-C8-alkyl)silyl, tri(C1-C8-alkyl)silyl-C1-C8-alkyl, C3-C7-cycloalkyl, C3-C7-halocycloalkyl, C3-C7-cycloalkenyl, C3-C7-halocycloalkenyl, C4-C10-cycloalkylalkyl, C4-C10-halocycloalkylalkyl, C6-C12-cycloalkylcycloalkyl, C1-C8-alkyl-C3-C7-cycloalkyl, C1-C8-alkoxy-C3-C7-cycloalkyl, tri(C1-C8-alkyl)silyl-C3-C7-cycloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, C2-C8-alkenyloxy, C2-C8-halo alkenyloxy, C3-C8-alkynyloxy, C3-C8-haloalkynyloxy, C1-C8-alkylamino, C1-C8-halo alkylamino, C1-C8-cyanoalkoxy, C4-C8-cycloalkylalkoxy, C3-C6-cycloalkoxy, C1-C8-alkylsulfanyl, C1-C8-haloalkylsulfanyl, C1-C8-alkylcarbonyl, C1-C8-haloalkylcarbonyl, arylcarbonyl, aryl-C1-C6-alkylcarbonyl, C3-C8-cycloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C1-C8-alkylcarbamoyl, di-C1-C8-alkylcarbamoyl, N—C1-C8-alkyloxycarbamoyl, C1-C8-alkoxycarbamoyl, N—C1-C8-alkyl-C1-C8-alkoxycarbamoyl, aminothiocarbonyl, C1-C8-alkoxycarbonyl, C1-C8-haloalkoxycarbonyl, C3-C8-cycloalkoxycarbonyl, C2-C8-alkoxyalkylcarbonyl, C2-C8-haloalkoxyalkylcarbonyl, C3-C10-cycloalkoxyalkylcarbonyl, C1-C8-alkylaminocarbonyl, di-C1-C8-alkylaminocarbonyl, C3-C8-cycloalkylaminocarbonyl, C1-C8-alkylcarbonyloxy, C1-C8-haloalkylcarbonyloxy, C3-C8-cycloalkylcarbonyloxy, C1-C8-alkylcarbonylamino, C1-C8-haloalkylcarbonylamino, C1-C8-alkylaminocarbonyloxy, di-C1-C8-alkylaminocarbonyloxy, C1-C8-alkyloxycarbonyloxy, C1-C8-alkylsulfonyl, C1-C8-haloalkylsulfonyl, C1-C8-alkylsulfonyloxy, C1-C8-haloalkylsulfonyloxy, C1-C8-alkylaminosulfamoyl, di-C1-C8-alkylaminosulfamoyl, (C1-C8-alkoxyimino)-C1-C8-alkyl, (C3-C7-cycloalkoxyimino)-C1-C8-alkyl, hydroxyimino-C1-C8-alkyl, (C1-C8-alkoxyimino)-C3-C7-cyclo alkyl, hydroxyimino-C3-C7-cyclo alkyl, (C1-C8-alkylimino)-oxy, (C1-C8-alkylimino)-oxy-C1-C8-alkyl, (C3-C7-cycloalkylimino)-oxy-C1-C8-alkyl, (C1-C6-alkylimino)-oxy-C3-C7-cyclo alkyl, (C1-C8-alkenyloxyimino)-C1-C8-alkyl, (C1-C8-alkynyloxyimino)-C1-C8-alkyl, (benzyloxyimino)-C1-C8-alkyl, C1-C8-alkoxyalkyl, C1-C8-alkylthioalkyl, C1-C8-alkoxyalkoxyalkyl, C1-C8-haloalkoxyalkyl, benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, benzyloxy, phenyloxy, benzylsulfanyl, benzylamino, phenylsulfanyl, or phenylamino;
• R4 represents hydrogen, fluorine, C1-C8-alkyl, C1-C8-haloalkyl or C1-C8-alkyloxy;
• R5 represents hydrogen, fluorine, C1-C8-alkyl, C1-C8-haloalkyl or C1-C8-alkyloxy;
• or
• R4 and R5 form together with the carbon atom to which they are attached an optionally halogen-, C1-C4-alkyl-, C1-C4-haloalkyl-, C1-C4-alkoxy-, C1-C4-haloalkoxy-, C1-C4-alkylthio- or C1-C4-haloalkylthio-substituted C3-C7-cycloalkyl ring;
• and
• Q2 represents a 5-membered partially unsaturated heterocycloalkyl comprising one or two heteroatom(s) or a 5-membered heteroaryl comprising one or two heteroatom(s), wherein the 5-membered partially unsaturated heterocycloalkyl or 5-membered heteroaryl is linked to the C(R4)(R5)-moiety via a ring carbon atom, and
• wherein the 5-membered partially unsaturated heterocycloalkyl or 5-membered heteroaryl is non-substituted or substituted by one or more group(s) selected from halogen, cyano, sulfanyl, pentafluoro-λ6-sulfanyl, C1-C8-alkyl, C1-C8-haloalkyl, C1-C8-cyanoalkyl, C1-C8-alkyloxy, C1-C8-haloalkyloxy, tri(C1-C8-alkyl)silyl, tri(C1-C8-alkyl)silyl-C1-C8-alkyl, C3-C7-cycloalkyl, C3-C7-halocycloalkyl, C3-C7-cycloalkenyl, C3-C7-halocycloalkenyl, C4-C10-cycloalkylalkyl, C4-C10-halocycloalkylalkyl, C6-C12-cycloalkylcycloalkyl, C1-C8-alkyl-C3-C7-cycloalkyl, C1-C8-alkoxy-C3-C7-cycloalkyl, tri(C1-C8-alkyl)silyl-C3-C7-cycloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, C3-C8-alkynyloxy, C3-C8-haloalkynyloxy, C1-C8-cyanoalkoxy, C4-C8-cycloalkylalkoxy, C3-C6-cycloalkoxy, C1-C8-alkylsulfanyl, C1-C8-haloalkylsulfanyl, C1-C8-alkylsulfinyl, C1-C8-haloalkylsulfinyl, C1-C8-alkylsulfonyl, C1-C8-haloalkylsulfonyl, C1-C8-alkylsulfonyloxy, C1-C8-haloalkylsulfonyloxy, C1-C8-alkoxyalkyl, C1-C8-alkylthio alkyl, C1-C8-alkoxyalkoxyalkyl, C1-C8-halo alkoxyalkyl, benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, 6-membered heteroaryloxy, benzyloxy, phenoxy, benzylsulfanyl, phenylsulfanyl,
• wherein the benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, 6-membered heteroaryloxy, benzyloxy, phenoxy, benzylsulfanyl, or phenylsulfanyl is non-substituted or substituted by one or more group(s) selected from halogen, CN, nitro, C1-C8-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or pentafluoro-λ6-sulfanyl;
• and/or a salt and/or N-oxide thereof.