# US 12,213,482 B2 · Fungicide enhancers effective for treating plants infected with fungal pathogens

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 12,213,482 B2
- Document ID: US12213482B2
- Status: Granted
- Kind: B2
- Application number: 17/407,959
- Filed: 2021-08-20
- Published: 2022-02-10
- Granted: 2025-02-04
- Earliest claimed: 2015-01-27
- Assignees: Board of Regents, The University of Texas System; CottonGen, LLC
- Applicants: Board of Regents, The University of Texas System; Cottongen, LLC
- Inventors: Stanley J. Roux; Gregory B. Clark; Simon L. Hiebert
- Web page: https://patentgrep.com/patent/US12213482B2

## CPC

- A01N 41/02: containing a sulfur-to-oxygen double bond
- A01N 37/02: Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
- A01N 37/26: containing the group [IMAGE cpc-sch-A01N-0936.gif]; Thio analogues thereof
- A01N 41/06: Sulfonic acid amides
- A01N 43/16: with oxygen as the ring hetero atom
- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A01N 59/20: Copper
- C12N 5/04: Plant cells or tissues {(culture media C12N5/0025)}
- A01N 2300/00: Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
- 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
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)

## Abstract

The present invention includes compositions and methods of for treating plants infected with fungal pathogens by contacting an infected plant or plant at risk of infection with a fungicidal composition comprising an fungicide selected from copper compound such as copper octanoate or copper hydroxide, or a triazole fungicide such as myclobutanil, propionazole, tebuconazole or epoxiconazole, an enhancer selected from apyrase inhibitors, e.g., N-(m-tolyl)-[1,1′-biphenyl]-4-sulfonamide, S-heptyl 2-oxo-2H-chromene 3-carbothioate, 3-(N-(4-bromophenyl) sulfamoyl)-N-(3-nitrophenyl)benzamide, or (E)-3-methyl-N-(1-(naphthalen-2-yl) ethylidene)benzohydrazide and, optionally, a phytologically-acceptable inert carrier.

## Claims

### Claim 1

A composition comprising a fungicide comprising:
a) copper octanoate, and an enhancer selected from N-(m-tolyl)-[1,1′-biphenyl]-4-sulfonamide, S-heptyl 2-oxo-2H-chromene-3-carbothioate, 3-(N-(4-bromophenyl) sulfamoyl)-N-(3-nitrophenyl)benzamide, or (E)-3-methyl-N′-(1-(naphthalen-2-yl)ethylidene);
b) myclobutanil and an enhancer selected from N-(m-tolyl)-[1,1′-biphenyl]-4-sulfonamide, S-heptyl 2-oxo-2H-chromene-3-carbothioate, 3-(N-(4-bromophenyl) sulfamoyl)-N-(3-nitrophenyl)benzamide, or (E)-3-methyl-N′-(1-(naphthalen-2-yl)ethylidene) benzohydrazide;
c) propiconazole and an enhancer selected from N-(m-tolyl)-[1,1′-biphenyl]-4-sulfonamide or 3-(N-(4-bromophenyl) sulfamoyl)-N-(3-nitrophenyl)benzamide;
d) tebuconazole and an enhancer selected from N-(m-tolyl)-[1,1′-biphenyl]-4-sulfonamide, S-heptyl 2-oxo-2H-chromene-3-carbothioate or 3-(N-(4-bromophenyl) sulfamoyl)-N-(3-nitrophenyl)benzamide
e) copper hydroxide and (E)-3-methyl-N′-(1-(naphthalen-2-yl)ethylidene) benzohydrazide;
f) prothioconazole and (E)-3-methyl-N′-(1-(naphthalen-2-yl)ethylidene) benzohydrazide; or
g) difenoconazole and (E)-3-methyl-N′-(1-(naphthalen-2-yl)ethylidene) benzohydrazide.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the composition further comprises a phytologically-acceptable inert carrier.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the amount of the fungicide is not effective for treating a fungus.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the amount of the fungicide is effective for treating a fungus and is adapted for application to a fungicide-resistant fungus.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the enhancer is provided at 0.005, 0.01, 0.05, 0.1, 0.5, 1.0, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.5, 3.0, 4.0, 5.0, 7.5, or 10% weight to weight enhancer to fungicide.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the enhancer is provided at 0.005, 0.01, 0.05, 0.1, 0.5, 1.0, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.5, 3.0, 4.0, 5.0, 7.5, or 10% volume to volume enhancer to fungicide.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the composition is synergistic and the weight ratio of the fungicide to the enhancer is between about 500:1 and 5000:1.

### Claim 8

A fungicide comprising:
a) copper octanoate; and an apyrase inhibitor selected from N-(m-tolyl)-[1,1′-biphenyl]-4-sulfonamide, S-heptyl 2-oxo-2H-chromene-3-carbothioate, 3-(N-(4-bromophenyl) sulfamoyl)-N-(3-nitrophenyl)benzamide, or (E)-3-methyl-N′-(1-(naphthalen-2-yl)ethylidene);
b) myclobutanil and an enhancer selected from N-(m-tolyl)-[1,1′-biphenyl]-4-sulfonamide, S-heptyl 2-oxo-2H-chromene-3-carbothioate, 3-(N-(4-bromophenyl) sulfamoyl)-N-(3-nitrophenyl)benzamide, or (E)-3-methyl-N′-(1-(naphthalen-2-yl)ethylidene) benzohydrazide;
c) propiconazole and an enhancer selected from N-(m-tolyl)-[1,1′-biphenyl]-4-sulfonamide or 3-(N-(4-bromophenyl) sulfamoyl)-N-(3-nitrophenyl)benzamide;
d) tebuconazole and an enhancer selected from N-(m-tolyl)-[1,1′-biphenyl]-4-sulfonamide, S-heptyl 2-oxo-2H-chromene-3-carbothioate or 3-(N-(4-bromophenyl) sulfamoyl)-N-(3-nitrophenyl)benzamide
e) copper hydroxide and (E)-3-methyl-N′-(1-(naphthalen-2-yl)ethylidene) benzohydrazide;
f) prothioconazole and (E)-3-methyl-N′-(1-(naphthalen-2-yl)ethylidene) benzohydrazide; or
g) difenoconazole and (E)-3-methyl-N′-(1-(naphthalen-2-yl)ethylidene) benzohydrazide, in amounts sufficient to treat a fungus.

### Claim 9 (depends on 8)

The fungicide of claim 8, wherein the fungicide is added to a growth media for growing cells.

### Claim 10 (depends on 8)

The fungicide of claim 8, wherein the cells are selected from at least one of bacterial, fungal, plant, animal, mammalian, yeast, amphibian, avian, nematode or insect cells.

### Claim 11 (depends on 8)

The fungicide of claim 8, wherein the composition is synergistic and the weight ratio of the fungicide to the apyrase inhibitor is between about 500:1 and 5000:1.