Pyrazole amide insecticides

A compound of Formula 1 (including all geometric and stereoisomers), N-oxides, and salts thereof:

• wherein
• X is O or S;
• each A is independently CH, N or CR1;
• each R1 is independently H, amino, cyano, halogen, nitro, C(S)NH2;
• or R1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl is optionally substituted with one or more R6;
• or
• R1 is phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or heteroaromatic ring is optionally substituted with one or more R6;
• or R1 is C3-C9-trialkylsilyl, C(O)R7, CR7(═NO)R7, C(O)OR7, C(O)NR7R8, NR7R8, NR8C(O)R7, NR8C(O)OR7, OR7, NHC(O)NR7R8, NR7S(O)pR9, OC(O)R7, OC(O)NR7R8, OC(O)OR7, S(O)pR9, SF5, SO2NR7R8, OS(O)2R9, or S(═NR11)OpR9;
• or R1 is a 3-membered to 7-membered partly or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1-4 nitrogen atoms optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, substituted by C(O)R7, C(O)OR7, C(O)NR7R8, S(O)pR7, or SO2NR7R8;
• R2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl is optionally substituted with one or more R6;
• or R2 is C1-C6 alkyl optionally substituted with one or more R6 and substituted by a phenyl or a 4 to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or heterocyclic ring is optionally substituted with one or more R6;
• or R2 is C(O)R7, C(O)OR7, NR7R8, OR7, S(O)pR9 or SO2NR7R8;
• R3 is C1-C3 alkyl or C1-C3 haloalkyl;
• R4 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl is optionally substituted with one or more R6;
• or R4 is C(O)R7, CR7(═NO)R7, C(O)OR7, C(O)NR7R8, NR7R8, NR8C(O)R7, NR8C(O)OR7, OR7, S(O)pR9, SO2NR7R8, or NR11SO2NR7R8;
• R5 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6-alkyl, C2-C6 alkenyl, C2-C6 alkynyl C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl is optionally substituted with one or more R6;
• or R5 is C(O)R7, CR7(═NO)R8, C(O)OR7, C(O)NR7R8, NR7R8, NR8C(O)R7, NR8C(O)OR7, NR11SO2NR7R8, OR7, S(O)pR9, or SO2NR7R8;
• each R6 is independently halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR10, C(O)NR7R8, NR7R8, NR8C(O)R7, NR8C(O)OR7, OR7, NHC(O)NR7R8, NR7S(O)pR9, OC(O)R7, OC(O)OR7, S(O)pR9, SO2NR7R8, or S(═NR)OpR7;
• each R7 is independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl is optionally substituted with one or more R12;
• or R7 is phenyl, or a 4 to 6-membered saturated, partly saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, wherein each phenyl or 4- to 6-membered heterocyclic ring is optionally substituted with one or more R12;
• each R8 is independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is optionally substituted with one or more R6;
• when R7 and R8 are on N, R7 and R8 can form a ring of 3 to 7 carbons, optionally including oxygen, S(O)p or NR7;
• each R9 is independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein each alkyl, alkenyl, alkynyl or cycloalkyl is optionally substituted with one or more R6;
• or R9 is phenyl, or a 4 to 6-membered saturated, partly saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, wherein each phenyl or 4- to 6-membered heterocyclic ring is optionally substituted with one or more R6;
• each R10 is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl;
• each R11 is independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl wherein each alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl is optionally substituted with one or more R6;
• C(O)R7, C(O)OR7, or S(O)pR7;
• R12 is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C8 cycloalkylalkyl, wherein each alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl is optionally substituted with halogen or cyano;
• Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups, and wherein thiazole is optionally substituted with one to two groups, these groups being chosen from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl is optionally substituted with one or more R6, C(O)R7, CR7(═NOR8), C(O)OR7, C(O)NR7R8, C(S)NR7R8, OR7, S(O)pR9, SO2NR7R8;
• NR7R8, NR8C(O)R7, NR8C(O)OR7, S(O)pR7, SO2NR7R8, or a 5-membered or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1-4 nitrogen atoms optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or a 3-membered to 7-membered partly or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1-4 nitrogen atoms optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, substituted by C(O)R7, C(O)OR7, C(O)NR7R8, S(O)pR7, SO2NR7R8;
• n is 1, 2, or 3;
• p is 0, 1, or 2.