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US 2019/0161499 A1Published application
Pesticidally active 1,2,4-triazole derivatives
AssigneeSyngenta Participations AG
InventorsAndrew Edmunds, Jürgen Harry Schaetzer, Aurelien Bigot, Sebastian Rendler, André Jeanguenat
Life of this patent
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Abstract
The present invention relates to 1,2,4-triazole derivatives, to processes for preparing them, to intermediates for preparing them, to pesticidli, in particular insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising those derivatives and to methods of using them to combat and control pests such as insect, acarine, mollusc and nematode pests.
Claims15
A compound of formula (I)
- wherein
- R1a is selected from H, cyano, halogen, C1-C6-alkyl, C3-C7-cycloalkyl, —C(═O)OH, —C(═O)R5, —C(═O)OR6, —C(═O)NR7R8, wherein each C1-C6-alkyl and C3-C7-cycloalkyl is unsubstituted or substituted with 1 to 7 substituents independently selected from halogen, cyano, C1-C6-alkoxy and —C(═O)O(C1-C6-alkyl);
- R1b is selected from H and C1-C6-alkyl;
- Z1 is selected from —(C0-C3-alkyl)-phenyl which is substituted with 1 to 4 substituents independently selected from R4a, a 5- or 6-membered heteroaromatic monocyclic ring and a 8-, 9- or 10-membered heteroaromatic bicyclic ring system, wherein the heteroaromatic monocyclic ring and bicyclic ring system is substituted with 1 to 3 substituents independently selected from R4a;
- Z2 is selected from —(C0-C3-alkyl)-phenyl which is substituted with 1 to 4 substituents independently selected from R4b, a 5- or 6-membered heteroaromatic monocyclic ring and a 8-, 9- or 10-membered heteroaromatic bicyclic ring system, wherein the heteroaromatic monocyclic ring and bicyclic ring system is substituted with 1 to 3 substituents independently selected from R4b;
- or
- Z2 is a fully or partially saturated 3 to 10 membered ring, wherein the ring members are selected from carbon atoms and 0 to 4 heteroatoms independently selected from 1 or 2 oxygen atoms, 1 or 2 sulphur atoms and 1 to 4 nitrogen atoms;
- wherein 0 to 3 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulphur atom ring members are independently selected from S, S(O) and S(O)2;
- and wherein the ring is unsubstituted or substituted with 1 to 4 substituents independently selected from R4b;
- Q is selected from
- (Q1)
- wherein
- M is selected from
- (i) —C(═O)—,
- (ii) —C(R3g)(A)-,
- (iii) —S—,
- (iv) —S(═O)—,
- (v) —S(═O)2—,
- (vi) —N(A1)-,
- (vii) —O—,
- (viii) —C(═N—O—R13)—,
- (ix) —C(═CR13a—O—R13b)—;
- J1 is selected from a direct bond, —C(R3aR3b)— and —C(R3aR3b)C(R3cR3d)—;
- J2 is selected from direct bond and —C(R3eR3f)—;
- (Q2)
- wherein
- B is a 3-7 membered fully or partially saturated ring, each ring or ring system containing ring members selected from carbon and 0-4 heteroatoms independently selected from 0-2 oxygen, 0-2 sulphur and 0-4 nitrogen atoms, wherein 0 to 3 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulphur atom ring members are independently selected from S, S(O) and S(O)2;
- and wherein the ring or ring system is unsubstituted or substituted with 1 to 4 R4c;
- J3 is selected from a direct bond, —C(R3aR3b)— and —C(R3aR3b)C(R3cR3d)—;
- J4 is selected from direct bond and —C(R3eR3f)—;
- (Q3),
- wherein
- E is a 3 to 7 membered fully or partially saturated ring, each ring or ring system containing ring members selected from carbon and 0-4 heteroatoms independently selected from 0-2 oxygen, 0-2 sulphur and 0-4 nitrogen atoms, wherein 0 to 3 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulphur atom ring members are independently selected from S, S(O) and S(O)2;
- and wherein the ring is unsubstituted or substituted with 1 to 4 substituents R4d;
- J5 is selected from a direct bond, —C(R3aR3b)— and —C(R3aR3b)C(R3cR3d)—;
- (Q4)
- wherein
- Z is —C(A2)-;
- J6 is selected from a direct bond and —C(R3eR3f)—;
- R2a, R2b, R2c and R2d are independently selected from H, halogen, cyano, nitro, —C(═O)R5, —C(═S)R5, —C(═O)OR6, —C(═O)NR7R8, —C(═S)NR7R8, —NR7C(═O)R8, —NR9R10, —SO2NR9R10, —SR11, —S(═O)R11, —S(═O)2R11, —OR12, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl, which C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl are unsubstituted or substituted with 1-4 substituents independently selected from halogen, cyano, nitro, OR12a, C1-C6-alkyl, C1-C6-haloalkyl, —SR11a, —S(═O)R11a and —S(═O)2R11a;
- or R2a and R2b together with the carbon atom to which they are attached or R2c and R2d together with the carbon atom to which they are attached are carbonyl or thiocarbonyl;
- or R2a and R2b together with the carbon atom to which they are attached or R2c and R2d together with the carbon atom to which they are attached form a C3-C7-cycloalkyl, which cycloalkyl is unsubstituted or substituted with 1 or 2 substituents independently selected from R4e;
- R3a, R3b, R3c, R3d, R3e and R3f are independently selected from H, halogen, cyano, —C(═O)R5, —C(═S)R5, —C(═O)OR6, —C(═O)NR7R8, —C(═S)NR7R8, —NR7C(═O)R8, —NR9R10, —SO2NR9R10, —SR11, —S(═O)R11, —S(═O)2R11, —OR12, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl, which C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl are unsubstituted or substituted with 1-4 substituents independently selected from halogen, cyano, nitro, OR12a, —SR11a, —S(═O)R11a and —S(═O)2R11a;
- or R3a and R3b together with the carbon atom to which they are attached or R3c and R3d together with the carbon atom to which they are attached or R3e and R3f together with the carbon atom to which they are attached are carbonyl or thiocarbonyl;
- or R3a and R3b together with the carbon atom to which they are attached or R3c and R3d together with the carbon atom to which they are attached or R3e and R3f together with the carbon atom to which they are attached form a C3-C7-cycloalkyl;
- which cycloalkyl is unsubstituted or substituted with 1 or 2 substituents independently selected from R4f;
- R3g is selected from H, halogen, cyano, nitro, —C(═O)R5, —C(═S)R5, —C(═O)OR6, —C(═O)NR7R8, —NR7C(═O)R8, —C(═S)NR7R8, —SR11, —S(═O)R11, —S(═O)2R11, —NR9R10, —S(═O)2NR9R10, OR12, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl, which C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl are unsubstituted or substituted with 1-4 substituents independently selected from halogen, cyano, nitro, OR12a, C1-C6-alkyl, C1-C6-haloalkyl, —SR11a, —S(═O)R11a and —S(═O)2R11a;
- A and A2 are independently selected from H, halogen, cyano, nitro, —C(═O)R5, —C(═S)R5, —C(═O)OR6, —C(═O)NR7R8, —NR7C(═O)R8, —C(═S)NR7R8, —NR9R10, —S(═O)2NR9R10, —SR11, —S(═O)R11, —S(═O)2R11, —OR12, —CR14(═NR9), —CR14═N—O—R13, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl, which C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl are unsubstituted or substituted with 1-4 substituents independently selected from halogen, cyano, nitro, OR12a, C1-C6-alkyl, C1-C6-haloalkyl, —SR11a, —S(═O)R11a and —S(═O)2R11a;
- or —(C0-C3-alkyl)-phenyl, a —(C0-C3-alkyl)-5-6 membered heteroaromatic ring or a 7-11 membered bicyclic ring system, each ring or ring system is unsubstituted or substituted with 1 to 3 R4g;
- A1 is selected from cyano, —C(═O)R5, —C(═S)R5, —C(═O)OR6, —C(═O)NR7R8, —C(═S)NR7R8, —NR7C(═O)R8, —NR9R10, —S(═O)2NR9R10, —S(═O)2R11, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl, which C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl are unsubstituted or substituted with 1-4 substituents independently selected from halogen, cyano, nitro, OR12a, C1-C6-alkyl, C1-C6-haloalkyl, —SR11a, —S(═O)R11a and —S(═O)2R11a;
- or —(C0-C3-alkyl)-phenyl, a —(C0-C3-alkyl)-5-6 membered heteroaromatic ring or a —(C0-C3-alkyl)-7-11 membered bicyclic ring system, each ring or ring system is unsubstituted or substituted with 1 to 3 R4h;
- R4a, R4b, R4c, R4d, R4e, R4f, R4g, R4h, R4i, R4j, R4k, R4l, R4m, R4n and R4o are independently selected from halogen, cyano, nitro, —C(═O)R5, —C(═S)R5, —C(═O)OR6, —C(═O)NR7R8, —NR7C(═O)R8, —C(═S)NR7R8, —NR9R10, —S(═O)2NR9R10, —SR11, —S(═O)—S(═O)2R11, OR12a, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl, —(C0-C3-alkyl)-phenyl, a —(C0-C3-alkyl)-5-6 membered heteroaromatic ring and C3-C7-cycloalkenyl, which C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl, —(C0-C3-alkyl)-phenyl, a —(C0-C3-alkyl)-5-6 membered heteroaromatic ring and C3-C7-cycloalkenyl are unsubstituted or substituted with 1-4 substituents independently selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, —SR11a, —S(═O)R11a and —S(═O)2R11a;
- R5 is selected from H, C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl, which C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl are unsubstituted or substituted with 1-4 substituents independently selected from halogen, cyano, nitro, OR12a, C1-C6-alkyl, C1-C6-haloalkyl, —SR11a, —S(═O)R11a and —S(═O)2R11a;
- or —(C0-C3-alkyl)-phenyl, a —(C0-C3-alkyl)-5-6 membered heteroaromatic ring or a —(C0-C3-alkyl)-7-11 membered bicyclic ring system, each ring or ring system is unsubstituted or substituted with 1 to 3 R4i;
- R6 is selected from C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl, which C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl are unsubstituted or substituted with 1-4 substituents independently selected from halogen, cyano, nitro, OR12a, C1-C6-alkyl, C1-C6-haloalkyl, —SR11a, —S(═O)R11a and —S(═O)2R11a;
- or —(C0-C3-alkyl)-phenyl, a —(C0-C3-alkyl)-5-6 membered heteroaromatic ring or a —(C0-C3-alkyl)-7-11 membered bicyclic ring system, each ring or ring system is unsubstituted or substituted with 1 to 3 R4j;
- R7 and R8 are independently selected from H, C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl, which C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl are unsubstituted or substituted with 1-4 substituents independently selected from halogen, cyano, nitro, OR12a, C1-C6-alkyl, C1-C6-haloalkyl, —SR11a, —S(═O)R11a and —S(═O)2R11a;
- or —(C0-C3-alkyl)-phenyl, a —(C0-C3-alkyl)-5-6 membered heteroaromatic ring or a —(C0-C3-alkyl)-7-11 membered bicyclic ring system, each ring or ring system is unsubstituted or substituted with 1 to 3 R4k;
- R9 and R10 are independently selected from H, —C(═O)R5, —C(═S)R5, —C(═O)OR6, —C(═O)NR7R8, —NR7C(═O)R8, C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy, —O—C3-C6-alkenyl, —O—C3-C6-alkynyl;
- C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl;
- which C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl are unsubstituted or substituted with 1-4 substituents independently selected from halogen, cyano, nitro, OR12a, C1-C6-alkyl, C1-C6-haloalkyl, —SR11a, —S(═O)R11a and —S(═O)2R11a;
- or —(C0-C3-alkyl)-phenyl, a —(C0-C3-alkyl)-5-6 membered heteroaromatic ring or a —(C0-C3-alkyl)-7-11 membered bicyclic ring system, each ring or ring system is unsubstituted or substituted with 1 to 3 R4l;
- or R9 and R10 together with the nitrogen atom to which they are attached form a 5 to 6 membered heterocyclyl;
- R11 is selected from C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl, which C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl are unsubstituted or substituted with 1-4 substituents independently selected from halogen, cyano, nitro, OR12a, C1-C6-alkyl, C1-C6-haloalkyl, —SR11a, —S(═O)R11a and —S(═O)2R11a;
- or —(C0-C3-alkyl)-phenyl, a —(C0-C3-alkyl)-5-6 membered heteroaromatic ring or a —(C0-C3-alkyl)-7-11 membered bicyclic ring system, each ring or ring system is unsubstituted or substituted with 1 to 3 R4m;
- R11a, R12a, R13a and R14 are independently selected from H, C1-C6-alkyl and C1-C6-haloalkyl;
- R12 is selected from H, C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl, which C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl are unsubstituted or substituted with 1-4 substituents independently selected from halogen, cyano, nitro, OR12a, C1-C6-alkyl, C1-C6-haloalkyl, —SR11a, —S(═O)R11a and —S(═O)2R11a;
- or —(C0-C3-alkyl)-phenyl, a —(C0-C3-alkyl)-5-6 membered heteroaromatic ring or a —(C0-C3-alkyl)-7-11 membered bicyclic ring system, each ring or ring system is unsubstituted or substituted with 1 to 3 R4n;
- R13 and R13b are independently selected from C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl, which C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl and C3-C7-cycloalkenyl are unsubstituted or substituted with 1-4 substituents independently selected from halogen, cyano, nitro, OR12a, C1-C6-alkyl, C1-C6-haloalkyl, —SR11a, —S(═O)R11a and —S(═O)2R11a;
- or —(C0-C3-alkyl)-phenyl, a —(C0-C3-alkyl)-5-6 membered heteroaromatic ring or a —(C0-C3-alkyl)-7-11 membered bicyclic ring system, each ring or ring system is unsubstituted or substituted with 1 to 3 R4o;
- or an agrochemically acceptable salt or N-oxide thereof.
68 more elements
Dependencies are inferred from the claim text.