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

1. A method of treating a food product with an antimicrobial agent, the method comprising:

administering a benzoxaborole treatment directly to one or more surfaces of a food packaging material, wherein the benzoxaborole treatment comprises one or more benzoxaborole compounds,

drying the one or more surfaces of the food packaging material,

vaporizing the benzoxaborole compound from the one or more surfaces of the food packaging material to treat the food product located therein,

wherein the benzoxaborole is 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 C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, hydroxy, halogen, nitro, nitrile, amino, amino substituted by one or more C 1 -C 6 -alkyl groups, carboxy, acyl, aryloxy, carbonamido, carbonamido substituted by C 1 -C 6 -alkyl, sulfonamido or trifluoromethyl or the fused ring may link two oxaborole rings;

X is a group —CR 7 R 8 wherein R 7 and R 8 are each independently hydrogen, C 1 -C 6 -alkyl, nitrile, nitro, aryl, arylalkyl or R 7 and R 8 together with the carbon atom to which they are attached form an alicyclic ring; and

R 6 is hydrogen, C 1 -C 18 -alkyl, C 1 -C 18 -alkyl substituted by C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, hydroxy, amino, amino substituted by C 1 -C 18 -alkyl, carboxy, aryl, aryloxy, carbonamido, carbonamido substituted by C 1 -C 6 -alkyl, aryl or arylalkyl, arylalkyl, aryl, heteroaryl, cycloalkyl, C 1 -C 18 -alkyleneamino, C 1 -C 18 -alkyleneamino substituted by phenyl, C 1 -C 6 -alkoxy or C 1 -C 6 -alkylthio, carbonyl alkyleneamino or a radical of formula (V):

wherein A, D and X are as defined herein before.

2. The method of claim 1 , wherein the food product is selected from the group consisting of a strawberry, a raspberry, a blackberry, and a blueberry.

3. The method of claim 1 , wherein the benzoxaborole compound is has the structure

or a salt thereof.

4. The method of claim 1 , wherein administering the benzoxaborole treatment to food packaging material further comprises embedding the benzoxaborole compound into the food packaging material, impregnating the food packaging material with the benzoxaborole compound, or coating the food packaging material with the benzoxaborole compound.

5. The method of claim 1 , wherein the food packaging material is a chamber.

6. A method of treating a food product with an antimicrobial agent, the method comprising:

administering a benzoxaborole treatment directly to one or more surfaces of a food packaging material, wherein the benzoxaborole treatment comprises one or more benzoxaborole compounds,

drying the one or more surfaces of the food packaging material,

vaporizing the benzoxaborole compound from the one or more surfaces of the food packaging material to treat the food product located therein,

wherein the benzoxaborole has the structure formula (A):

R A -L A -G-L B -R B   (A),

wherein

each of R A and R B is independently a of R A and R B is of formula (E):

wherein each R 6 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;

X 2 ═(CR 6 2 ) m where m=1 or 2;

each of L A and L B is independently —O— or

each of R and R′ is independently hydrogen, unsubstituted or substituted C 1-18 -alkyl, arylalkyl, aryl, or heterocyclic moiety; and

G is a substituted or unsubstituted C 1-18 -alkylene, arylalkylene, arylene, or heterocyclic moiety; and acceptable salts thereof.

7. The method of claim 6 , wherein the food product is selected from the group consisting of a strawberry, a raspberry, a blackberry, and a blueberry.

8. The method of claim 6 , wherein the benzoxaborole has the structure

or a salt thereof.

9. The method of claim 6 , wherein administering the benzoxaborole treatment to food packaging material further comprises embedding the benzoxaborole compound into the food packaging material, impregnating the food packaging material with the benzoxaborole compound, or coating the food packaging material with the benzoxaborole compound.

10. The method of claim 6 , wherein the food packaging material is a chamber.

11. The method of claim 5 , wherein the chamber is a clamshell.

12. The method of claim 11 , wherein the clamshell comprises polyethylene terephthalate.

13. The method of claim 5 , wherein the chamber further comprises a liquid-absorbing material.

14. The method of claim 13 , wherein the liquid-absorbing material is comprised in a chamber component selected from the group consisting of a liner, a wrapping, a label, a tag, a sticker, and a pad.

15. The method of claim 13 , wherein the liquid-absorbing material provides for quick-release or slow-release of the benzoxaborole treatment to the food product comprised in the chamber over a time period.

16. The method of claim 10 , wherein the chamber is a clamshell.

17. The method of claim 16 , wherein the clamshell comprises polyethylene terephthalate.

18. The method of claim 10 , wherein the chamber further comprises a liquid-absorbing material.

19. The method of claim 18 , wherein the liquid-absorbing material is comprised in a chamber component selected from the group consisting of a liner, a wrapping, a label, a tag, a sticker, and a pad.

20. The method of claim 18 , wherein the liquid-absorbing material provides for quick-release or slow-release of the benzoxaborole treatment to the food product comprised in the chamber over a time period.