# US 10,765,117 B2 · Volatile applications against pathogens > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,765,117 B2 - Document ID: US10765117B2 - Status: Granted - Kind: B2 - Application number: 16/123,735 - Filed: 2018-09-06 - Published: 2019-01-03 - Granted: 2020-09-08 - Earliest claimed: 2013-01-30 - Assignees: Agrofresh Inc. - Applicants: Agrofresh Inc. - Inventors: Daniel Maclean; David H. Young; Richard M. Jacobson; Maurice C. Yap; Rodrigo A. Cifuentes; Donald H. DeVries; Joseph D. Eckelbarger - Web page: https://patentgrep.com/patent/US10765117B2 ## CPC - A01N 55/08: containing boron - A01N 25/18: Vapour or smoke emitting compositions with delayed or sustained release - A01N 55/00: 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) - A23B 2/721: in a controlled atmosphere comprising other gases in addition to CO2, N2, O2 or H2O - A23B 4/16: in the form of gases, e.g. fumigation; Compositions or apparatus therefor - A23B 4/20: Organic compounds; Microorganisms; Enzymes - A23B 7/152: in a controlled atmosphere comprising other gases in addition to CO2, N2, O2 or H2O {; Elimination of such other gases} - A23B 7/154: Organic compounds; Microorganisms; Enzymes - A61K 9/0034: {Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants} - A61K 9/70: Web, sheet or filament bases {; Films; Fibres of the matrix type containing drug (hollow drug-filled fibres A61K9/0092)} - A61K 31/69: Boron compounds - Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change - A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS - A23B: PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE ## 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 ### Claim 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 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; and contacting the one or more seeds with the volatile antimicrobial compound. ### Claim 2 (depends on 1) The method of claim 1, wherein the step of providing includes providing the compound of formula (IV) in gaseous form. ### Claim 3 (depends on 2) The method of claim 2, wherein the volatile antimicrobial compound has a structure of or a salt thereof. ### Claim 4 (depends on 3) The method of claim 3, wherein the volatile antimicrobial compound has a structure of or a salt thereof. ### Claim 5 (depends on 2) 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. ### Claim 6 (depends on 5) The method of claim 5, wherein the volatile antimicrobial compound has a structure of or a salt thereof. ### Claim 7 (depends on 6) The method of claim 6, wherein the volatile antimicrobial compound has a structure of or a salt thereof. ### Claim 8 (depends on 7) The method of claim 7 wherein the one or more seeds are corn, rice, rye, millet, barley, or wheat. ### Claim 9 (depends on 5) 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. ### Claim 10 (depends on 9) 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. ### Claim 11 (depends on 1) 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., Chalaraspp., 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., Pyriculariaspp., Pythium spp., Rhizoctonia spp., Rhizopus spp., Sclerotium spp., Sclerotinia spp., Septoriaspp., Sphaceloma spp., Sphaeropsis spp., Stemphyllium spp., Stilbella spp., Thelaviopsis spp., Thyronectria spp., Trachysphacra spp., Uromyces spp., Ustilago spp., Venturia spp., and Verlicillium spp. ### Claim 12 (depends on 11) The method of claim 11, wherein the pathogen is Botrytis spp., Penicillium spp., Alternaria spp., Monilinia spp., Glomerella spp., or Aspergillusspp. ### Claim 13 (depends on 12) The method of claim 12, wherein the pathogen is Aspergillus spp. ### Claim 14 (depends on 13) The method of claim 13, wherein the one or more seeds are corn, rice, rye, millet, barley, or wheat. ### Claim 15 (depends on 13) The method of claim 13, wherein the volatile antimicrobial compound has a structure of or a salt thereof. ### Claim 16 (depends on 1) 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. ### Claim 17 (depends on 16) The method of claim 16, wherein the volatile antimicrobial compound has a structure of or a salt thereof. ### Claim 18 (depends on 1) 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. ### Claim 19 (depends on 18) The method of claim 18, wherein the volatile antimicrobial compound has a structure of or a salt thereof.