Substituted pyrazole-containing compounds and their use as pesticides

A compound of formula (I)

• wherein
• A1 is N,
• A2 is C—R2,
• A3 is N,
• Q is selected from phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
• R1 is selected from the group consisting of halogen;
• cyano;
• azido;
• nitro;
• —SCN;
• SF5;
• C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R7;
• C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R7;
• C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R7;
• C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R7;
• —Si(R14)2R13;
• —OR8;
• —OS(O)nR8;
• —SR8;
• —S(O)mR8;
• —S(O)nN(R9a)R9b;
• —N(R9a)R9b;
• —N(R9a)C(═O)R7;
• C(═O)R7;
• —C(═O)OR8;
• —C(═NR9a)H;
• —C(═NR9a)R7;
• —C(═O)N(R9a)R9b;
• C(═S)N(R9a)R9b;
• phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10;
• and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
• R2 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, —SCN, SF5, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R7, C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R7, C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R7, C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R7, —Si(R14)2R13, —OR8, OS(O)nR8, —SR8, —S(O)mR8, —S(O)nN(R9a)R9b, —N(R9a)R9b, N(R9a)C(═O)R7, —C(═O)R7, —C(═O)OR8, —C(═S)R7, —C(═S)OR8, —C(═NR9a)R7, —C(═O)N(R9a)R9n, —C(═S)N(R9a)R9b, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
• R3 is selected from the group consisting of nitro, —NR9aR9b;
• —S(O)nN(R9a)R9b;
• —C(═O)N(R9a)R9b;
• —C(═S)N(R9a)R9b;
• —C(═NR9a)—S(O)mR8, —P(O)G2, —PG3, —N═N—R9a;
• R4 is selected from the group consisting of hydrogen, cyano, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R7, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, where the alkyl moiety in the four last-mentioned radicals may be substituted by one or more radicals R7, C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R7, C3-C8-cycloalkyl-C1-C4-alkyl where the cycloalkyl moiety may be partially or fully halogenated and/or may be substituted by one or more radicals R7, C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R7, C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R7, —N(R9a)R9b;
• —N(R9a)C(═O)R7;
• —Si(R14)2R13;
• —OR8;
• —SR8;
• —S(O)mR8;
• —S(O)nN(R9a)R9b;
• —C(═O)R7;
• —C(═O)OR8;
• —C(═O)N(R9a)R9b;
• —C(═S)R7;
• —C(═S)OR8, —C(═S)N(R9a)R9b;
• C(═NR9a)—S(O)mR8, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
• or R3 and R4 form together with the nitrogen they are bound to a group of the formula A.1
• or R3 and R4 form together with the nitrogen atom they are bound a 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
• provided that R3 and R4 do not form together with the nitrogen atom they are bound a substituted or unsubstituted piperidine, pyrrolidine or morpholine;
• G is selected independently from each other and independently of each occurrence from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylamino, C1-C6-dialkylamino, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy, benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals independently selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
• R5 and R6 each independently are C1-C12-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R7, C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R7, C2-C12-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R7, C2-C12-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R7, —C(═O)R7, —C(═NOR8)R7, —C(═NN(R9a)R9b)R7, —C(═O)OR7, —C(═O)N(R9a)R9B, —OC(═O)R7, —OC(═O)OR8, —NR9aC(═O)R7, —N[C(═O)R7]2, —NR7C(═O)OR8, —C(═O)N(R9a)—N(R9b)2, —C(═O)NR9a—NR9b[C(═O)R7], —NR9a—C(═O)N(R9b)2, —NR9a—NR9bC(═O)R7, —NR9a—N[C(═O)R7]2, —N[(C═O)R7]—N(R9a)2, —NR9a—NR9b[(C═O)OR8], —NR9a[(C═O)N(R9b)2], —NR9a[C═NR9b]R7, —NR9a(C═NR9b)N(R9b)2, —O—N(R9a)2, —O—NR9a(C═O)R7, —SO2NR9aR9b, —NR9aSO2R8, —SO2OR8, —OSO2R8, —OR8, —NR9aR9b, —SR8, —Si(R14)2R13, —PR9aR9b, —SOR8, —SO2R8, or —P(═O)tG2, —P(═O)2G2;
• or R5 and R6 together with the sulfur atom to which they are attached form a saturated, partially unsaturated or unsaturated 3- to 8-membered ring which optionally contains 1 to 4 further heteroatoms selected from the group consisting of oxygen, nitrogen, and sulfur, which ring can be fused with one or two saturated, partially unsaturated or unsaturated 5- to 6-membered rings which may contain 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen, and sulfur, wherein all of the above rings are unsubstituted or substituted by any combination of 1 to 6 groups R18;
• each R7 is independently selected from the group consisting of cyano, azido, nitro, —SCN, SF5, C1-C4-alkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —Si(R14)2R13, —OR8, —OSO2R8, —SR8, —S(O)mR8, —S(O)nN(R9a)R9b, —N(R9a)R9b, —C(═O)N(R9a)R9b, —C(═S)N(R9a)R9b, —C(═O)OR8, —C(═O)R19, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
• and, in case R7 is bound to a cycloalkyl group or to a heterocyclic ring, R7 may additionally be selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl and benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10;
• and in groups —C(═O)R7, —C(═S)R7, —C(═NR9a)R7 and —N(R9a)C(═O)R7, R7 may additionally be selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl and benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10;
• or two geminally bound radicals R7 together form a group selected from the group consisting of ═CR11R12, ═S(O)mR8, ═S(O)mN(R9a)R9b, ═NR9a, ═NOR8 and ═NNR9aR9b;
• or two radicals R7, together with the carbon atoms to which they are bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members;
• each R8 is independently selected from the group consisting of hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, —Si(R14)2R13, —SR20, —S(O)mR20, —S(O)nN(R9a)R9b,
• —N(R9a)R9b, —N═CR15R16, —C(═O)R17, —C(═O)N(R9a)R9b, —C(═S)N(R9a)R9b, —C(═O)OR20, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
• with the proviso that R8 is not C1-C6-alkoxy or C1-C6-haloalkoxy if it is bound to an oxygen atom;
• R9a, R9b are, independently of each other and independently of each occurrence, selected from the group consisting of hydrogen, cyano, C1-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, where the alkyl moiety in the four last-mentioned radicals may be substituted by one or more radicals R19, C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C8-cycloalkyl-C1-C4-alkyl where the cycloalkyl moiety may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, —N(R21)R22;
• —N(R21)C(═O)R19;
• —Si(R14)2R13;
• —OR20;
• —SR20;
• —S(O)mR20, —S(O)nN(R21)R22;
• —C(═O)R19;
• —C(═O)OR20;
• —C(═O)N(R21)R22;
• —C(═S)R17;
• C(═S)OR20, —C(═S)N(R21)R22;
• —C(═NR21)R17—S(O)mR20, —S(O)nN(R21)R22,
• phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
• or R9a and R9b together form a group ═CR11R12;
• or R9a and R9b, together with the nitrogen atom to which they are bound, may form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring which may additionally containing 1 or 2 further heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R10;
• each R10 is independently selected from the group consisting of halogen, cyano, azido, nitro, —SCN, SF5, C1-C10-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C3-C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C2-C10-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, C2-C10-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R19, —Si(R14)2R13, —OR20, —OS(O)nR20, —SR20, —S(O)mR20, —S(O)nN(R21)R22, —N(R21)R22, C(═O)R19, —C(═O)OR20, —C(═NR21)R22;
• —C(═S)N(R21)R22, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
• and a 3-, 4-, 5-, 6- or 7-membered saturated or unsaturated heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, which may be substituted by one or more radicals independently selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
• or two radicals R10 bound on adjacent atoms together form a group selected from the group consisting of —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O—, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —SCH2CH2S—, —SCH2SCH2—, —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2C(═S)S—, —C(═S)SCH2—, —S(CH2)S—, —CH2CH2NR21—, —CH2CH═N—, —CH═CH—NR21—, —OCH═N— and —SCH═N—, thus forming, together with the atoms to which they are bound, a 5- or 6-membered ring, where the hydrogen atoms of the above groups may be replaced by one or more substituents selected from the group consisting of halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy or one or more CH2 groups of the above groups may be replaced by a C═O group;
• R11, R12 are, independently of each other and independently of each occurrence, selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy,
• —C(═O)R19, —C(═O)OR20, —C(═NR21)R22, —C(═O)N(R21)R22, —C(═S)N(R21)R22, phenyl which may be substituted by 1, 2, 3, 4, or 5 radicals R10;
• and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, which may be substituted by one or more radicals R10;
• R13, R14 are, independently of each other and independently of each occurrence, selected from the group consisting of C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl;
• R15, R16 are, independently of each other and independently of each occurrence, selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, phenyl which may be substituted by 1, 2, 3, 4, or 5 radicals R10;
• and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, which may be substituted by one or more radicals R10;
• each R17 is independently selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, phenyl and benzyl;
• each R18 is independently defined like R2;
• each R19 is independently selected from the group consisting of cyano, azido, nitro, —SCN, SF5, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —Si(R14)2R13, —OR20, —OSO2R20, —SR20, —S(O)mR20, —S(O)nN(R21)R22, —N(R21)R22, —C(═O)N(R21)R22, —C(═S)N(R21)R22, —C(═O)OR20, —C(═O)R20, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
• and, in case R19 is bound to a cycloalkyl group, R19 may additionally be selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl;
• and in groups —C(═O)R19, R19 may additionally be selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl;
• or two geminally bound radicals R19 together form a group selected from the group consisting of ═CR11R12, ═S(O)mR20, ═S(O)mN(R21)R22, ═NR21, ═NOR20 and ═NNR21;
• or two radicals R19, together with the carbon atoms to which they are bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members;
• each R20 is independently selected from the group consisting of hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, —Si(R14)2R13, C1-C6-alkylaminosulfonyl, amino, C1-C6-alkylamino, di-(C1-C6-alkyl)-amino, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, aminocarbonyl, C1-C6-alkylaminocarbonyl, di-(C1-C6-alkyl)-aminocarbonyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy, benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals independently selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
• with the proviso that R20 is not C1-C6-alkoxy or C1-C6-haloalkoxy if it is bound to an oxygen atom;
• R21 and R22 are independently of each other and independently of each occurrence selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy, benzyl which may be substituted by 1, 2, 3, 4 or 5 radicals independently selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals independently selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
• or R21 and R22, together with the nitrogen atom to which they are bound, may form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring which may additionally containing 1 or 2 further heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
• each m is independently 1 or 2;
• each n is independently 0, 1 or 2;
• p is 0, 1, 2, 3, 4 or 5;
• t is 0 or 1;
• or a stereoisomer, N-oxide, tautomer or agriculturally or veterinarily acceptable salt thereof.