IP Library Granted Patent US 10,765,117
Granted Patent B2
US 10,765,117 · App. 16/123,735 · Granted Sep 8, 2020

Volatile applications against pathogens

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Quick Facts
Patent No.
US 10,765,117
App. No.
16/123,735
Granted
Sep 8, 2020
Kind
B2
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.

Claims (32)

1. A method of using a volatile antimicrobial compound against pathogens affecting one or more seeds, the method comprising:

providing a volatile antimicrobial compound 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; and

contacting the one or more seeds with the volatile antimicrobial compound.

2. The method of claim 1 , wherein the step of providing includes providing the compound of formula (IV) in gaseous form.

3. The method of claim 2 , wherein the volatile antimicrobial compound has a structure of

or a salt thereof.

4. The method of claim 3 , wherein the volatile antimicrobial compound has a structure of

or a salt thereof.

5. The method of claim 2 , wherein the step of contacting includes contacting the one or more seeds with the compound of formula (IV) in gaseous form.

6. The method of claim 5 , wherein the volatile antimicrobial compound has a structure of

or a salt thereof.

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

or a salt thereof.

8. The method of claim 7 wherein the one or more seeds are corn, rice, rye, millet, barley, or wheat.

9. The method of claim 5 , wherein the method comprises a treatment selected from the group consisting of treatment during field packing, treatment during palletization or after palletization, in open pallets or in wrapped pallets, in tents, in-box treatments with or without liners, in sea container, truck or other container types used during transportation, and treatment during storage.

10. The method of claim 9 , wherein the step of providing is selected from the group consisting of release from a sachet, release from a synthetic or natural film, release from liner or other packaging materials, release from powder, release from a gas-releasing generator, release using a compressed or non-compressed gas cylinder, release from a droplet inside a box, and combinations thereof.

11. The method of claim 1 , wherein the pathogen is selected from the group consisting of Acremonium spp., Albugo spp., Alternaria spp., Ascochyta spp., Aspergillus spp., Botryodiplodia spp., Botryaspheria 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., Khusicia 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., Pestalatiopsis 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., Thelaviopsis spp., Thyronectria spp., Trachysphacra spp., Uromyces spp., Ustilago spp., Venturia spp., and Verlicillium spp.

12. The method of claim 11 , wherein the pathogen is Botrytis spp., Penicillium spp., Alternaria spp., Monilinia spp., Glomerella spp., or Aspergillus spp.

13. The method of claim 12 , wherein the pathogen is Aspergillus spp.

14. The method of claim 13 , wherein the one or more seeds are corn, rice, rye, millet, barley, or wheat.

15. The method of claim 13 , wherein the volatile antimicrobial compound has a structure of

or a salt thereof.

16. The method of claim 1 , wherein the method comprises a treatment selected from the group consisting of treatment during field packing, treatment during palletization or after palletization, in open pallets or in wrapped pallets, in tents, in-box treatments with or without liners, in sea container, truck or other container types used during transportation, and treatment during storage.

17. The method of claim 16 , wherein the volatile antimicrobial compound has a structure

of or a salt thereof.

18. The method of claim 1 , wherein the step of providing is selected from the group consisting of release from a sachet, release from a synthetic or natural film, release from liner or other packaging materials, release from powder, release from a gas-releasing generator, release using a compressed or non-compressed gas cylinder, release from a droplet inside a box, and combinations thereof.

19. The method of claim 18 , wherein the volatile antimicrobial compound has a structure of

or a salt thereof.

Assignments (4)
AGREEMENT OF AGENT RESIGNATION, APPOINTMENT AND ACCEPTANCE & MASTER ASSIGNMENT OF SECURITY DOCUMENTS Recorded Jun 24, 2024
From: JPMORGAN CHASE BANK, N.A.
To: ALTER DOMUS US LLC
Reel/Frame 067914/0941 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT REEL 053316, FRAME 0561 Recorded Apr 3, 2023
From: BANK OF MONTREAL
To: AGROFRESH, INC.
Reel/Frame 063238/0901 →
SECURITY INTEREST Recorded Mar 31, 2023
From: AGROFRESH INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 063214/0683 →
PATENT SECURITY AGREEMENT Recorded Jul 27, 2020
From: AGROFRESH, INC.
To: BANK OF MONTREAL, AS COLLATERAL AGENT
Reel/Frame 053316/0561 →