Succinate dehydrogenase inhibitors and methods of making and using the same

A compound having a structure of Formula (I):

• wherein:
• X is NH or O;
• ring A is C6-10 aryl or 5-12 membered heteroaryl having 1-3 ring heteroatoms selected from N, O, and S;
• each of R1 and R2 is independently selected from H, halo, C1-18 alkyl, C2-18 alkenyl, C2-18 alkynyl, C1-18 alkoxy, C1-18 haloalkyl, C1-18 hydroxyalkyl, C(O)NHC1-18alkyl, C(O)OC1-18alkyl, C(O)SC1-18alkyl, C2-18 heteroalkyl having 1-3 backbone heteroatoms selected from N, O, and S, C6-10 aryl, or 5-8 membered heteroaryl having 1-3 ring heteroatoms selected from N, O, and S;
• or
• R1 and R2 together form C2-6 alkenyl, C3-8 cycloalkyl, or C3-8 heterocycloalkyl having 1-3 ring heteroatoms selected from N, O, and S, optionally substituted with 1-3 R3 groups;
• each R3 is independently halo, CN, OH, NO2, C1-6 alkoxy, C1-6 alkyl, C1-6 hydroxyalkyl, C1-6 haloalkyl, or C1-6 haloalkylene-OH
• R4 is C2-6 alkyl, C1-6 haloalkyl, C1-6 heteroalkyl having 1-3 backbone heteroatoms selected from N, O, and S, C3-8 cycloalkyl, C6-10 aryl, 3-12 membered heterocycloalkyl having 1-3 ring heteroatoms selected from N, O, and S, or 5-12 membered heteroaryl having 1-3 ring heteroatoms selected from N, O, and S, and the aryl or heteroaryl group is optionally substituted with 1-3 R3 groups;
• and
• n is 0, 1, 2, or 3;
• with the proviso that if ring A is C6 aryl, n is 0, and R1 and R2 are each H, then R4 is not unsubstituted phenyl.