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US 11,440,900 B2Granted
Agricultural chemicals
AssigneeGlobachem NV
InventorsChristopher John Urch, Victoria Elizabeth Jackson, Linda Jordan, Effi Baetzner, Oliver James Stephen McGaw
Life of this patent
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Abstract
The present invention relates to benzimidazole and benzotriazole compounds which are of use in the field of agriculture as fungicides, wherein the compounds include benzimidazole and benzotriazole compounds having a structure according to formula 1, or an agronomically acceptable salt or N-oxide thereof:
Claims20
A compound of formula I, or an agronomically acceptable salt or N-oxide thereof:
- Y1 is selected from CH and N;
- Z1, Z2 and Z3 are each independently selected from N and CR6;
- wherein at least one of Z1, Z2 and Z3 is CR6;
- R1 and R10 are each independently at each occurrence selected from:
- C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, halo, nitro, OR7, SR8, OS(O)2R8, S(O)2R8, C(O)OR8, C(O)NR8R8, C(O)R8, S(O)2NR8R8, S(O)(NR8)R8, S(O)R8, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR8R9;
- R2 and R6 are each independently at each occurrence selected from H, halo, nitro, cyano, C1-C6-alkyl, C3-C6-cycloalkyl and C1-C6-haloalkyl;
- R3, R5a and R5b are independently at each occurrence selected from H, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, halo, nitro, OR7, SR8, OS(O)2R8, S(O)2R8, C(O)OR8, C(O)NR8R8, C(O)R8, S(O)2NR8R8, S(O)(NR8)R8, S(O)R8, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR8R9;
- R4a and R4b are independently at each occurrence selected from H, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, halo, nitro, SR8, OS(O)2R8, S(O)2R8, C(O)OR8, C(O)NR8R8,C(O)R8, S(O)2NR8R8, S(O)(NR8)R8, S(O)R8, cyano, C2-C6-alkenyl, C2-C6-alkynyl, or wherein R4b and R5b together with the carbon atoms to which they are attached together form a ring selected from:
- phenyl, 5- or 6-membered heteroaryl, 5-, 6- or 7-membered heterocycloalkyl ring and C5-C7-cycloalkyl;
- said heteroaryl or phenyl ring being optionally substituted with from 1 to 4 R10 groups or said heterocycloalkyl or cycloalkyl ring being optionally substituted with from 1 to 4 R11 groups;
- with the proviso that either at least one of R4a and R4b is selected from C1-C6-alkyl, C1-C6-haloalkyl, halo, nitro, SR8, OS(O)2R8, S(O)2R8, S(O)2NR8R8, S(O)(NR8)R8, S(O)R8, cyano, C2-C6-alkenyl, and C2-C6-alkynyl or R4b and R5b together form a ring;
- R7 is independently at each occurrence selected from:
- H, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl and C1-C6-haloalkyl;
- R8 is independently at each occurrence selected from:
- H, C3-C6-cycloalkyl and C1-C6-alkyl;
- or where two R8 groups are attached to the same nitrogen atom, said R8 groups, together with said nitrogen atom form a 4-, 5-, 6- or 7-membered heterocycloalkyl ring;
- R9 is independently at each occurrence selected from;
- H, C1-C6-alkyl, C(O)—C1-C6-alkyl and S(O)2—C1-C6-alkyl;
- or where an R8 group and an R9 group are attached to the same nitrogen atom, said R8 and R9 groups, together with said nitrogen atom form a 4-, 5-, 6- or 7-membered heterocycloalkyl ring;
- R11 is independently at each occurrence selected from:
- ═O, ═S, C1-C6-alkyl, C1-C6-haloalkyl, halo, nitro, OR8, SR8, OS(O)2R8, S(O)2R8, S(O)2NR8R8, S(O)(NR8)R8, S(O)R8, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR8R9;
- and
- x is an integer from 0 to 4;wherein for any R1, R2, R3, R4a, R4b, R5a, R5b, R6, R7, R8, R9, R10, or R11 group that is alkyl, alkenyl, cycloalkyl, heterocycloalkyl (including where two R8 groups or an R8 group and an R9 group together with a nitrogen to which they are attached form a heterocycloalkyl ring), alkynyl, C(O)-alkyl or S(O)2-alkyl is optionally substituted, where chemically possible, by 1 to 4 substituents which are each independently selected at each occurrence from the group consisting of:
- ═O;
- ═NRa, ═NORa, C1-C4-alkyl, halo, nitro, cyano, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, NRaRb, S(O)2Ra, S(O)Ra, S(O)(NRa)Ra, S(O)2NRaRa, CO2Ra, C(O)Ra, CONRaRa and ORa;
- wherein Ra is independently selected from H and C1-C4-alkyl;
- and Rb is independently H, C1-C4-alkyl, C(O)—C1-C4-alkyl, S(O)2—C1-C4-alkyl.
24 more elements
Dependencies are inferred from the claim text.