Back to results
US 11,634,390 B2Granted
Agricultural chemicals
AssigneeGlobachem NV
InventorsChristopher John Urch, Victoria Elizabeth Jackson, Calum William Muir
Life of this patent
Estimating the term…
Abstract
The present invention relates to compounds which are of use in the field of agriculture as herbicides. The invention also relates to methods of using said compounds and compositions comprising said compounds.
Claims27
A compound of formula I:
- wherein
- R1 has the structure
- R13 is independently at each occurrence selected from C1-C6-alkyl, C1-C6-haloalkyl, halogen, nitro, OR10, SR10, cyano, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl and NR10R11;
- R14 is independently selected from H and C1-C6-alkyl;
- and n is an integer independently selected from 0, 1 and 2;
- R2 is independently at each occurrence selected from C1-C6-alkyl, C1-C6-haloalkyl, halogen, nitro, OR10, SR10, OS(O)2R10, S(O)2R10, S(O)2NR10R10, S(O)(NR10)R10, S(O)R10, cyano, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl and NR10R11;
- R3 is independently selected from:
- H, C1-C6-alkyl and C3-C6-cycloalkyl;
- R4 is independently selected from H, fluoro, chloro, C1-C6-haloalkyl and C1-C6-alkyl;
- R5 and R6 together with the carbon atom to which they are attached form a cyclic group selected from C3-C8-cycloalkyl and 4- to 8-membered heterocycloalkyl;
- wherein the cyclic group is optionally substituted with from 1 to 4 R12 groups;
- R7 and R12 are independently at each occurrence selected from:
- ═O, ═S, C1-C6-alkyl, C1-C6-haloalkyl, halogen, nitro, OR10, SR10, S(O)2R10, S(O)2NR10R10, S(O)(NR10)R10, S(O)R10, C(O)R10, C(O)NR10R10, C(O)OR10, cyano, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, 3-to 6-membered heterocycloalkyl and NR10R11;
- R10 is independently at each occurrence selected from:
- H and C1-C6-alkyl;
- R11 is independently at each occurrence selected from;
- H, C1-C6-alkyl, C(O)—C1-C6-alkyl and S(O)2-C1-C6-alkyl;
- p is an integer independently selected from 0, 1, 2 and 3;
- wherein any R2, R3, R4, R7, R10, R11, R12 group that is alkyl, cycloalkyl, or heterocycloalkyl 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-C6-alkyl, halo, nitro, cyano, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-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-C6-alkyl;
- and Rb is independently H, C1-C6-alkyl, C(O)—C1-C6-alkyl, or S(O)2-C1-C6-alkyl;
- or an agronomically acceptable salt or N-oxide thereof.
21 more elements
A herbicidal composition comprising an effective amount of an active compound of formula I:
- wherein
- R1 is selected from 5- to 9-membered bicyclic or monocyclic heterocycloalkyl group and 5-, 6-, 9- or 10-membered heteroaryl group;
- wherein said heterocycloalkyl or heteroaryl group comprises at least one nitrogen atom in the ring and is optionally substituted with from 1 to 6 R7 groups;
- or wherein R1 is —N═CR8R9 wherein R8 and R9 together with the carbon atom to which they are attached form a 5- to 9-membered bicyclic or monocyclic heterocycloalkyl group;
- wherein said heterocycloalkyl group comprises at least one nitrogen atom in the ring and is optionally substituted with from 1 to 6 R7 groups;
- R2 is independently at each occurrence selected from C1-C6-alkyl, C1-C6-haloalkyl, halogen, nitro, OR10, SR10, OS(O)2R10, S(O)2R10, S(O)2NR10R10, S(O)(NR10)R10, S(O)R10, cyano, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl and NR10R11;
- R3 is independently selected from:
- H, C1-C6-alkyl and C3-C6-cycloalkyl;
- R4 is independently selected from H, fluoro, chloro, C1-C6-haloalkyl and C1-C6-alkyl;
- R5 and R6 together with the carbon atom to which they are attached form a cyclic group selected from C3-C8-cycloalkyl and 4- to 8-membered heterocycloalkyl;
- wherein the cyclic group is optionally substituted with from 1 to 4 R12 groups;
- R7 and R12 are independently at each occurrence selected from:
- ═O, ═S, C1-C6-alkyl, C1-C6-haloalkyl, halogen, nitro, OR10, SR10, S(O)2R10, S(O)2NR10R10, S(O)(NR10)R10, S(O)R10, C(O)R10, C(O)NR10R10, C(O)OR10, cyano, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, 3-to 6-membered heterocycloalkyl and NR10R11;
- R10 is independently at each occurrence selected from:
- H and C1-C6-alkyl;
- R11 is independently at each occurrence selected from;
- H, C1-C6-alkyl, C(O)—C1-C6-alkyl and S(O)2-C1-C6-alkyl;
- p is an integer independently selected from 0, 1, 2 and 3;
- wherein any R2, R3, R4, R7, R10, R11, R12 group that is alkyl, cycloalkyl, or heterocycloalkyl 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-C6-alkyl, halo, nitro, cyano, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-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-C6-alkyl;
- and Rb is independently H, C1-C6-alkyl, C(O)—C1-C6-alkyl, or S(O)2-C1-C6-alkyl;
- or an agronomically acceptable salt or N-oxide thereof.
21 more elements
Dependencies are inferred from the claim text.