US 12,415,815 B2
Pyrido[2,3-e]oxazine derivatives as agricultural chemicals
Victoria Elizabeth Jackson, Sint-Truiden (BE); Linda Jordan, Sint-Truiden (BE); and Ryan Neil Burgin, Sint-Truiden (BE)
Assigned to GLOBACHEM NV, Sint-Truiden (BE)
Appl. No. 17/794,799
Filed by GLOBACHEM NV, Sint-Truiden (BE)
PCT Filed Jan. 27, 2021, PCT No. PCT/EP2021/051814
§ 371(c)(1), (2) Date Jul. 22, 2022,
PCT Pub. No. WO2021/151919, PCT Pub. Date Aug. 5, 2021.
Claims priority of application No. 2001181 (GB), filed on Jan. 28, 2020.
Prior Publication US 2023/0151023 A1, May 18, 2023
Int. Cl. C07D 498/04 (2006.01); A01N 43/90 (2006.01); C07D 519/00 (2006.01)
CPC C07D 498/04 (2013.01) [A01N 43/90 (2013.01); C07D 519/00 (2013.01)] 17 Claims
 
1. A compound of formula I, or an agronomically acceptable salt or N-oxide thereof:

OG Complex Work Unit Chemistry
X1 and X2 are each independently selected from carbon and nitrogen;
Y1 is independently selected from O and S;
═Y2 is independently selected from =O and =S;
Z1 is independently absent or is selected from C(O)O, OC(O), O, S, S(O), S(O)2, C(O)NR5, NR5C(O), S(O)2NR5, NR5S(O)2, S(O)NR5, NR5S(O), CR6R7, C(O), C(S), C═NOR8, C1-C3-alkylene and NR5;
R1 and R12 are each independently at each occurrence selected from C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, halogen, nitro, OR9, SR10, OS(O)2R10, S(O)2R10, C(O)OR10, C(O)NR10R10, C(O)R10, S(O)2NR10R10, S(O)(NR10)R10, S(O)R10, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR10R11;
R2 is independently at each occurrence selected from C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, halogen, nitro, OR9, SR10, OS(O)2R10, S(O)2R10, C(O)OR10, C(O)NR10R10, C(O)R10, S(O)2NR10R10, S(O)(NR10)R10, S(O)R10, cyano, C2-C6-alkenyl, C2-C6-alkynyl, NR10R11 and phenyl optionally substituted with from 1 to 5 R12 groups;
R3 is independently at each occurrence selected from C3-C8-alkyl and C0-C3-alkylene-R3a;
wherein R3a is independently at each occurrence selected from phenyl, 5- or 6-membered heteroaryl, 5-, 6-, 7- or 8-membered heterocycloalkyl and C3-C8-cycloalkyl; said heterocycloalkyl or cycloalkyl group being monocyclic or bicyclic; said heteroaryl or phenyl group being optionally substituted with from 1 to 5 R12 groups or said heterocycloalkyl or cycloalkyl group being optionally substituted with from 1 to 4 R13 groups; said heterocycloalkyl or cycloalkyl group being optionally fused to phenyl or a 5- or 6-membered heteroaryl, said heteroaryl or phenyl group being optionally substituted with from 1 to 4 R12 groups;
R4 is independently at each occurrence selected from: C1-C6-alkyl, C3-C6-cycloalkyl and C1-C6-haloalkyl;
R5 and R10 are each independently at each occurrence selected from: H, C3-C6-cycloalkyl, C1-C6-alkyl and benzyl;
or where two R10 groups are attached to the same nitrogen atom, said R10 groups, together with said nitrogen atom form a 4-, 5-, 6- or 7-membered heterocycloalkyl ring;
R6 is independently at each occurrence selected from: H, C3-C6-cycloalkyl, C1-C6-alkyl, phenyl and 5- or 6-membered heteroaryl;
R7 is independently at each occurrence selected from: H, halo and OR8;
R8 is each independently at each occurrence selected from: H, C3-C6-cycloalkyl, C1-C6-alkyl and C1-C3-alkylene-R8a; wherein R8a is independently at each occurrence selected from phenyl and 5- or 6-membered heteroaryl;
R9 is independently at each occurrence selected from: H, C1-C6-alkyl, C0-C3-alkylene-C3-C6-cycloalkyl, C(O)—C1-C6-alkyl and C1-C6-haloalkyl;
R11 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 R10 group and an R11 group are attached to the same nitrogen atom, said R10 and R11 groups, together with said nitrogen atom form a 4-, 5-, 6- or 7-membered heterocycloalkyl ring;
R13 is independently at each occurrence selected from: =O, ═S, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl; halogen, nitro, OR9, SR10, OS(O)2R10, S(O)2R10, S(O)2NR10R10, S(O)(NR10)R10, S(O)R10, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR10R11;
y is independently an integer selected from 0, 1 and 2;
m is independently an integer selected from 0, 1, 2 and 3; and
wherein any aforementioned alkyl, alkylene, alkenyl, cycloalkyl, heterocycloalkyl (including where two R10 groups or an R10 group and an R11 group together with a nitrogen to which they are attached form a heterocycloalkyl ring), alkynyl, C(O)-alkyl, S(O)2-alkyl and benzyl 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, ORa and SRa;
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.