IP Library Granted Patent US 9,138,001
Granted Patent B2
US 9,138,001 · App. 14/167,093 · Granted Sep 22, 2015

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

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,138,001
App. No.
14/167,093
Granted
Sep 22, 2015
Kind
B2
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.

Claims (18)

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):

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 1 -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;

and contacting a meat, plant, or plant part with an effective amount of the volatile antimicrobial compound in gaseous form.

2. 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., Thielaviopsis spp., Thyronectria spp., Trachysphacra spp., Uromyces spp., Ustilago spp., Venturia spp., and Verlicillium spp.

3. The method of claim 1 , wherein the pathogen is selected from the group consisting of Erwinia spp., Pantoea spp., Pectobacterium spp., Pseudomonas spp., Ralstonia spp., Xanthomonas spp.; Salmonella spp., Escherichia spp., Lactobacillus spp., Leuconostoc spp., Listeria spp., Shigella spp., Staphylococcus spp., Candida spp., Debaryomyces spp., Bacillus spp., Campylobacter spp., Clavibacter spp., Clostridium spp., Cryptosporidium spp., Giardia spp., Vibrio spp., Xanthomonas spp., and Yersinia spp.

4. 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.

5. The method of claim 1 , wherein the plants or plant parts are selected from the group consisting of corn, wheat, cotton, rice, soybean, and canola.

6. The method of claim 1 , wherein the plants Or plant parts are selected from the group consisting of fruit, vegetables, nursery, turf and ornamental crops.

7. The method of claim 6 , wherein the fruit is selected from the group consisting of banana, pineapple, citrus, grapes, watermelon, cantaloupe, muskmelon, and other melons, apple, peach, pear, cherry, kiwifruit, mango, nectarine, guava, papaya, persimmon, pomegranate, avocado, fig, citrus, and berries.

8. The method of claim 7 , wherein the berries are selected from the group consisting of strawberry, blueberry, raspberry, and blackberry.

9. The method of claim 7 , wherein and the citrus is selected from the group consisting of oranges, lemon, lime, and grapefruit.

10. The method of claim 1 , wherein the contacting comprises applying the volatile antimicrobial compound by ways selected from the group consisting of spray, mist, thermal or non-thermal fogging, drench, gas treatment, and combinations thereof.

11. The method of claim 10 , wherein the gas treatment 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.

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

Assignments (9)
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 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT REEL 036243, FRAME 0244 Recorded Apr 3, 2023
From: BANK OF MONTREAL
To: AGROFRESH, INC.
Reel/Frame 063238/0848 →
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 →
SECURITY INTEREST Recorded Jul 31, 2015
From: AGROFRESH INC.
To: BANK OF MONTREAL, AS ADMINISTRATIVE AGENT
Reel/Frame 036243/0244 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 17, 2015
From: ROHM AND HAAS COMPANY; DOW GLOBAL TECHNOLOGIES LLC; DOW AGROSCIENCES LLC
To: AGROFRESH INC
Reel/Frame 035932/0335 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 8, 2014
From: ECKELBARGER, JOSEPH D
To: DOW AGROSCIENCES LLC
Reel/Frame 033052/0940 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 3, 2014
From: MACLEAN, DANIEL; YOUNG, DAVID H; JACOBSON, RICHARD M; YAP, MAURICE C; DEVRIES, DONALD H; CIFUENTES, RODRIGO A
To: DOW AGROSCIENCES LLC
Reel/Frame 032599/0616 →