Deuterated antimicrobial compounds

A method for treating a microbial infection comprising administering to a subject in need thereof a therapeutically effective amount of a compound of Formula IA, IB, or IC:

• or an azoxy dimer or pharmaceutically acceptable salt thereof;
• wherein
• R1 is 2-(C1-C6)alkyl-1,4-dioxa-8-azaspiro[4.5]decan-8-yl or 4-((C3-C6)cycloalkyl methyl)piperazin-1-yl;
• R2 is halo, cyano, —(C1-C3)alkyl, or —O(C1-C3)alkyl, wherein —(C1-C3)alkyl or —O(C1-C3)alkyl has 2 to 7 halo substituents;
• R3 and R4 are independently H, D, halo, hydroxyl, cyano, —(C1-C6)alkyl, wherein at least one of R3 or R4 is D;
• and
• R5 is H, D, halo, hydroxyl, cyano, —(C1-C6)alkyl;
• thereby killing or inhibiting the growth of at least a portion of a plurality of microorganisms in the subject.

A compound of Formula IA, IB, or IC:

• or an azoxy dimer or salt thereof;
• wherein
• R1 is 2-(C1-C6)alkyl-1,4-dioxa-8-azaspiro[4.5]decan-8-yl or 4-((C3-C6)cycloalkyl methyl)piperazin-1-yl;
• R2 is halo, cyano, —(C1-C3)alkyl, or —O(C1-C3)alkyl, wherein —(C1-C3)alkyl or —O(C1-C3)alkyl has 2 to 7 halo substituents;
• R3 and R4 are independently H, D, halo, hydroxyl, cyano, —(C1-C6)alkyl, wherein at least one of R3 or R4 is D;
• and
• R5 is H, D, halo, hydroxyl, cyano, —(C1-C6)alkyl.