Large-scale methods of uniformly coating packaging surfaces with a volatile antimicrobial to preserve food freshness

A large-scale method of treating a plurality of chambers with an antimicrobial agent, the method comprising:

• placing a plurality of chambers in a position to be treated wherein each of the chambers comprise one or more surfaces,
• administering the antimicrobial treatment to one or more surfaces of the plurality of chambers during preformation, formation, or postformation of the plurality of chambers, wherein the antimicrobial treatment comprises one or more benzoxaborole compounds,
• drying the one or more surfaces of the plurality of chambers, and affixing the benzoxaborole compound to the one or more surfaces of the plurality of chambers,
• wherein the one or more benzoxaborole compounds are:
• i) of formula (IV), or a salt thereof:
• wherein A and D together with the carbon atoms to which they are attached form a 5-, 6-, or 7-membered fused ring which may be substituted by C1-C6-alkyl, C1-C6-alkoxy, hydroxy, halogen, nitro, nitrile, amino, amino substituted by one or more C1-C6-alkyl groups, carboxy, acyl, aryloxy, carbonamido, carbonamido substituted by C1-C6-alkyl, sulfonamido or trifluoromethyl or the fused ring may link two oxaborole rings;
• X is a group —CR7R8 wherein R7 and R8 are each independently hydrogen, C1-C6-alkyl, nitrile, nitro, aryl, arylalkyl or R7 and R8 together with the carbon atom to which they are attached form an alicyclic ring;
• and
• R6 is hydrogen, C1-C18-alkyl, C1-C18-alkyl substituted by C1-C6-alkoxy, C1-C6-alkylthio, hydroxy, amino, amino substituted by C1-C18-alkyl, carboxy, aryl, aryloxy, carbonamido, carbonamido substituted by C1-C6-alkyl, aryl or arylalkyl, arylalkyl, aryl, heteroaryl, cycloalkyl, C1-C18-alkyleneamino, C1-C18-alkyleneamino substituted by phenyl, C1-C6-alkoxy or C1-C6-alkylthio, carbonyl alkyleneamino or a radical of formula (V):
• wherein A, D and X are as defined herein before, or
• ii) formula (A):
• RA-LA-G-LB-RB (A),
• wherein
• each of RA and RB is independently a of RA and RB is of formula (E):
• wherein each R6 is independently hydrogen, alkyl, alkene, alkyne, haloalkyl, haloalkene, haloalkyne, alkoxy, alkeneoxy, haloalkoxy, aryl, heteroaryl, arylalkyl, arylalkene, arylalkyne, heteroarylalkyl, heteroarylalkene, heteroarylalkyne, halogen, hydroxyl, nitrile, amine, ester, carboxylic acid, ketone, alcohol, sulfide, sulfoxide, sulfone, sulfoximine, sulfilimine, sulfonamide, sulfate, sulfonate, nitroalkyl, amide, oxime, imine, hydroxylamine, hydrazine, hydrazone, carbamate, thiocarbamate, urea, thiourea, carbonate, aryloxy, or heteroaryloxy;
• n=1, 2, 3, or 4;
• B is boron;
• X2=(CR62)m where m=1 or 2;
• each of LA and LB is independently —O— or
• each of R and R′ is independently hydrogen, unsubstituted or substituted C1-18-alkyl, arylalkyl, aryl, or heterocyclic moiety;
• and
• G is a substituted or unsubstituted C1-18-alkylene, arylalkylene, arylene, or heterocyclic moiety;
• and acceptable salts thereof.