Vaporized administration of pesticides

1. A method of treating plants or plant parts with an antimicrobial compound, said method comprising:

a) volatilizing an antimicrobial treatment to form a vapor,

b) cooling the vapor to form the antimicrobial compound, wherein the antimicrobial compound is a solid, and

c) administering the solid antimicrobial compound to one or more plants or plant parts,

wherein the antimicrobial treatment comprises a fungicide selected from the group consisting of oxaborole, imazalil, fludioxonil, thiabendazole, and a benzoxaborole, and

wherein the step of administering the solid antimicrobial compound to one or more plants or plant parts is performed in a chamber.

2. The method of claim 1 , wherein the one or more plants or plant parts is selected from the group consisting of a strawberry, a grape, an apple, an orange, and a blueberry.

3. The method of claim 1 , wherein the antimicrobial treatment is a solid or a liquid.

4. The method of claim 3 , wherein the step of cooling the vapor forms solid microparticles.

5. The method of claim 4 , wherein the solid microparticles have a size of 2 micron or less.

6. The method of claim 4 , wherein the solid microparticles are in the form of a powder.

7. The method of claim 1 , wherein the fungicide is selected from the group consisting of oxaborole, imazalil, fludioxonil, and thiabendazole.

8. The method of claim 1 , wherein the fungicide is a benzoxaborole.

9. The method of claim 8 , wherein the benzoxaborole has the structure of formula (IV):

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;

and pharmaceutically acceptable salts thereof.

10. The method of claim 8 , wherein the benzoxaborole has the structure of formula (VI):

wherein each R 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=(CR 2 ) m where m=1, 2, 3, or 4;

Y is alkyl, alkene, alkyne, haloalkyl, haloalkene, haloalkyne, alkoxy, alkeneoxy, haloalkoxy, aryl, heteroaryl, arylalkyl, arylalkene, arylalkyne, heteroarylalkyl, heteroarylalkene, heteroarylalkyne, 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;

with a proviso that R is not aryloxy or heteroaryloxy when Y is hydroxyl;

and pharmaceutically acceptable salts thereof.

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

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

13. The method of claim 1 , wherein the fungicide is administered at a rate of about 0.001 mg/L to about 5 mg/L.

14. The method of claim 1 , wherein the method is effective in inhibiting plant pathogens selected from the group consisting of Acremonium spp., Albugo spp., Alternaria spp., Ascochyta spp., Aspergillus spp., Botryodiplodia spp., Botryospheria spp., Botrytis spp., Byssochlamys spp., Candida spp., Cephalosporium spp., Ceratocystis spp., Cercospora spp., Chalara spp., Cladosporium spp., Colletotrichum spp., Cryptosporiopsis spp., Cylindrocarpon spp., Debaryomyces spp., Diaporthe spp., Didymella spp., Diplodia spp., Dothiorella spp., Elsinoe spp., Fusarium spp., Geotrichum spp., Gloeosporium spp., Glomerella spp., Helminthosporium spp., Khuskia spp., Lasiodiplodia spp., Macrophoma spp., Macrophomina spp., Microdochium spp., Monilinia spp., Monilochaethes spp., Mucor spp., Mycocentrospora spp., Mycosphaerella spp., Nectria spp., Neofabraea spp., Nigrospora spp., Penicillium spp., Peronophythora spp., Peronospora spp., Pestalotiopsis spp., Pezicula spp., Phacidiopycnis spp., Phoma spp., Phomopsis spp., Phyllosticta spp., Phytophthora spp., Polyscytalum spp., Pseudocercospora spp., Pyricularia spp., Pythium spp., Rhizoctonia spp., Rhizopus spp., Sclerotium spp., Sclerotinia spp., Septoria spp., Sphaceloma spp., Sphaeropsis spp., Stemphyllium spp., Stilbella spp., Thielaviopsis spp., Thyronectria spp., Trachysphaera spp., Uromyces spp., Ustilago spp., Venturia spp., Verticillium spp., Bacillus spp., Campylobacter spp., Clavibacter spp., Clostridium spp., Erwinia spp., Escherichia spp., Lactobacillus spp., Leuconostoc spp., Listeria spp., Pantoea spp., Pectobacterium spp., Pseudomonas spp., Ralstonia spp., Salmonella spp., Shigella spp., Staphylococcus spp., Vibrio spp., Xanthomonas spp., and Yersinia spp.

15. The method of claim 1 , wherein the method is effective in inhibiting plant pathogens selected from the group consisting of Botrytis cinerea, Mucor piriformis, Fusarium sambucinum, Aspergillus brasiliensis , and Penicillium expansum.

16. The method of claim 1 , wherein the temperature of the chamber ranges from about −2° C. to about 25° C.

17. The method of claim 1 , wherein the temperature of the chamber ranges from about 0° C. to about 23° C.

18. The method of claim 1 , wherein the chamber is semipermeable or impermeable.

19. The method of claim 1 , wherein the antimicrobial treatment is sublimated to form the vapor.