Volatile applications against pathogens

Patent metadata

Field	Value
Publication number	US-2016374344-A9
Application number	US-201514690929-A
Country	US
Kind code	A9
Filing date	Apr 20, 2015
Priority date	Jan 30, 2013
Publication date	Dec 29, 2016
Grant date	—

Abstract

This invention is related to the use of a volatile antimicrobial compound against pathogens affecting humans comprising contacting infected areas with an atmosphere containing an effective amount of a volatile antimicrobial compound in gaseous form. The volatile antimicrobial compounds provided include certain oxaborole compounds, for example benzoxaboroles. Delivery systems are provided to take advantage of the volatile nature of these antimicrobial compounds. The method and use disclosed can be combined with other volatile compounds.

First claim

We claim:

1 . A method of using a volatile antimicrobial compound against pathogens, comprising:
contacting areas infected by the pathogens with an atmosphere containing an effective amount of the volatile antimicrobial compound in gaseous form, the volatile antimicrobial compound having a 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 or agriculturally acceptable salts thereof.

2 . The method of claim 1 , wherein the areas affected by the pathogens are selected from the group consisting of vaginal yeast infections, athlete's foot, tinea, or combinations thereof.

3 . The method of claim 1 , wherein the pathogens are selected from the group consisting of Candida albicans, C. tropicalis, C. glabrata, C. krusei, C. parapsilosis, C. dubliniensis, C. lusitaniae, Epidermophyton flocoosum, Trichiphyton rubrum, Trichophyton mentagrophytes , or combinations thereof.

4 . The method of claim 1 , further comprising impregnating, microencapsulating, or coating a material for releasing the volatile antimicrobial compound in a gaseous form.

5 . The method of claim 1 , wherein the volatile antimicrobial compound remain in its gaseous form for seven days.

6 . The method of claim 1 , wherein the volatile antimicrobial compound has a structure of

7 . A method of using a volatile antimicrobial compound against pathogens, comprising:
(a) mixing a volatile antimicrobial compound with an organic solvent; (b) heating the mixture from step (a) to evaporate the organic solvent and render the volatile antimicrobial compound into its gaseous form; and (c) contacting areas infected by the pathogens with an atmosphere containing an effective amount of the volatile antimicrobial compound in gaseous form at a temperature between 1° C. and 50° C.; wherein the volatile antimicrobial compound having a structure of formula (IV):

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 or agriculturally acceptable salts thereof.

8 . The method of claim 7 , wherein the areas affected by the pathogens are selected from the group consisting of vaginal yeast infections, athlete's foot, tinea, or combinations thereof.

9 . The method of claim 7 , wherein the pathogens are selected from the group consisting of Candida albicans, C. tropicalis, C. glabrata, C. krusei, C. parapsilosis, C. dubliniensis, C. lusitaniae, Epidermophyton flocoosum, Trichiphyton rubrum, Trichophyton mentagrophytes , or combinations thereof.

10 . The method of claim 7 , wherein the volatile antimicrobial compound remain in its gaseous form for seven days.

11 . The method of claim 7 , wherein the volatile antimicrobial compound has a structure of

12 . The method of claim 7 , wherein the organic solvent comprise acetone or ethanol.

13 . A method of using a volatile antimicrobial compound against pathogens, comprising:
contacting areas infected by the pathogens with an atmosphere containing an effective amount of the volatile antimicrobial compound in gaseous form, the volatile antimicrobial compound having a structure of formula (A1) or (A2):

wherein each of A 1 , A 2 , D 1 , and D 2 is independently hydrogen, substituted or unsubstituted C 1-18 -alkyl, arylalkyl, aryl, or heterocyclic; or A 1 and D 1 , or A 2 and D 2 together form a 5, 6, or 7-membered fused ring which is substituted or unsubstituted;
each of R 13 , R 16 , R 17 , R 18 , and R 19 is independently hydrogen, substituted or unsubstituted C 1-6 -alkyl, nitrile, nitro, aryl or aryl alkyl; or R 16 and R 17 , or R 18 and R 19 together form an alicyclic ring which is substituted or unsubstituted;
B is boron;
G is a substituted or unsubstituted C 1-18 -alkylene, arylalkylene, arylene, or heterocyclic moiety;
and pharmaceutically or agriculturally acceptable salts thereof.

14 . The method of claim 13 , wherein the areas affected by the pathogens are selected from the group consisting of vaginal yeast infections, athlete's foot, tinea, or combinations thereof.

15 . The method of claim 13 , wherein the pathogens are selected from the group consisting of Candida albicans, C. tropicalis, C. glabrata, C. krusei, C. parapsilosis, C. dubliniensis, C. lusitaniae, Epidermophyton flocoosum, Trichiphyton rubrum, Trichophyton mentagrophytes , or combinations thereof.

16 . The method of claim 13 , further comprising impregnating, microencapsulating, or coating a material for releasing the volatile antimicrobial compound in a gaseous form.

17 . The method of claim 13 , wherein the volatile antimicrobial compound remain in its gaseous form for seven days.

18 .

Assignees

• Agrofresh Inc

Inventors

• Malefyt Tim
• Maclean Daniel

Classifications

• A01N55/00

  Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur (containing organo-phosphorus compounds A01N57/00) · CPC title

• A23B4/16

  in the form of gases, e.g. fumigation; Compositions or apparatus therefor · CPC title

• A23B7/152

  in a controlled atmosphere comprising other gases in addition to CO2, N2, O2 or H2O {; Elimination of such other gases} · CPC title

• A23B7/154

  Organic compounds; Microorganisms; Enzymes · CPC title

• A61K31/69

  Boron compounds · CPC title