Use of benzoxaboroles as volatile antimicrobial agents on meats, plants, or plant parts

Patent metadata

Field	Value
Publication number	US-9426996-B2
Application number	US-201414294057-A
Country	US
Kind code	B2
Filing date	Jun 2, 2014
Priority date	Jan 30, 2013
Publication date	Aug 30, 2016
Grant date	Aug 30, 2016

Abstract

This invention is related to use of a volatile antimicrobial compound against pathogens affecting meats, plants, or plant parts. 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. Also combinations with a volatile plant growth regulator, for example 1-methylcyclopropene, are disclosed.

First claim

We claim:

1. A method of using a volatile antimicrobial compound against pathogens affecting meats, plants, or plant parts, comprising providing in gaseous form a volatile antimicrobial compound of formula (IV):

contacting a meat, plant, or plant part with an effective amount of the volatile antimicrobial compound in gaseous form; and
contacting the meat, plant, or plant part with an effective amount of a cyclopropene compound in gaseous form;
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 except for boronophthalide;

and agriculturally acceptable salts thereof.

2. The method of claim 1 , wherein the pathogen is at least one member selected from the group consisting of Acremonium spp., Albugo spp., Alternaria spp., Ascochyta spp., Aspergillus spp., Bacillus spp., Botryodiplodia spp., Botryospheria spp., Botrytis spp., Byssochlamys spp., Campylobacter spp., Candida spp., Cephalosporium spp., Ceratocystis spp., Cercospora spp., Chalara spp., Cladosporium spp., Clavibacter spp., Clostridium spp., Colletotrichum spp., Cryptosporidium spp., Cryptosporiopsis spp., Cylindrocarpon spp., Debaryomyces spp., Diaporthe spp., Didymella spp., Diplodia spp., Dothiorella spp., Elsinoe spp., Erwinia spp., Escherichia spp., Fusarium spp., Geotrichum spp., Giardia spp., Gloeosporium spp., Glomerella spp., Helminthosporium spp., Khuskia spp., Lactobacillus spp., Lasiodiplodia spp., Leuconostoc spp., Listeria spp., Macrophoma spp., Macrophomina spp., Microdochium spp., Monilinia spp., Monilochaethes spp., Mucor spp., Mycocentrospora spp., Mycosphaerella spp., Nectria spp., Neofabraea spp., Nigrospora spp., Pantoea spp., Pectobacterium 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., Pseudomonas spp., Pyricularia spp., Pythium spp., Ralstonia spp., Rhizoctonia spp., Rhizopus spp., Salmonella spp., Sclerotium spp., Sclerotinia spp., Septoria spp., Shigella spp., Sphaceloma spp., Sphaeropsis spp., Staphylococcus spp., Stemphyllium spp., Stilbella spp., Thielaviopsis spp., Thyronectria spp., Trachysphaera spp., Uromyces spp., Ustilago spp., Venturia spp., Verticillium spp., Vibrio spp., Xanthomonas spp., and Yersinia spp.

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

4. The method of claim 1 , wherein the plants or plant parts are selected from the group consisting of asparagus, sugar beet, barley, broccoli, cabbage, carrot, cassava, cauliflower, celery, cucumber, eggplant, garlic, grapevine, lettuce, spinach, leek, mushroom, onion, peas, pepper, bell pepper, potato, pumpkin, rye, sweet potato, squash, tobacco, tomato, snap bean, sorghum, sugarcane, corn, wheat, cotton, rice, soybean, canola, fruit, vegetables, nursery, turf, flowers, carnation, geranium, lily, orchid, rose, sunflower, ornamental flowers and ornamental crops.

5. The method of claim 4 , wherein the fruit is selected from the group consisting of apple, avocado, banana, strawberry, blueberry, raspberry, blackberry, cherry, oranges, lemon, lime, grapefruit, fig, grapes, guava, kiwifruit, mango, nectarine, cantaloupe, muskmelon, watermelon, papaya, peach, pear, persimmon, pineapple, and pomegranate.

6. The method of claim 4 , wherein the meat is selected from the group consisting of beef, bison, chicken, deer, goat, turkey, pork, sheep, fish, shellfish, mollusks and dry-cured meat products.

7. The method of claim 1 , wherein the contacting comprises applying the volatile antimicrobial compound by a gas treatment 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 or droplets placed inside a box, release from a mist or fog applied into a container and combinations thereof.

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

9. A method of using a volatile antimicrobial compound against pathogens affecting meats, plants, or plant parts, comprising placing a meat, plant or plant part in a container;
introducing into the container and in contact with the meat, plant or plant part an effective amount of a gaseous form of a volatile antimicrobial compound 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):

Assignees

• Agrofresh Inc

Inventors

• Maclean Daniel
• Young David H
• Jacobson Richard M
• Yap Maurice C
• Cifuentes Rodrigo A
• Devries Donald H
• Eckelbarger Joseph D

Classifications

• A23V2002/00

  Food compositions, function of food ingredients or processes for food or foodstuffs · CPC title

• A23B7/154

  Organic compounds; Microorganisms; Enzymes · CPC title

• A23B4/16

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

• A23B4/20

  Organic compounds; Microorganisms; Enzymes · 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