# US 10,477,865 B2 · Fungicidal compounds and methods of their use

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- Number: US 10,477,865 B2
- Document ID: US10477865B2
- Status: Granted
- Kind: B2
- Application number: 14/987,251
- Filed: 2016-01-04
- Published: 2016-07-07
- Granted: 2019-11-19
- Earliest claimed: 2009-12-09
- Assignees: Auckland Uniservices Limited
- Applicants: Auckland UniServices Limited
- Inventors: Silas Granato Villas-Boas
- Web page: https://patentgrep.com/patent/US10477865B2

## CPC

- A61K 31/357: having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N 63/30: Microbial fungi; Substances produced thereby or obtained therefrom
- A61K 36/06: Fungi, e.g. yeasts
- A61K 36/062: Ascomycota
- A61P 31/10: Antimycotics
- C07D 321/02: Seven-membered rings
- C07D 493/08: Bridged systems
- C12N 1/145: Fungi isolates
- C12P 17/181: {Heterocyclic compounds containing oxygen atoms as the only ring heteroatoms in the condensed system, e.g. Salinomycin, Septamycin}
- C12R 2001/645: Fungi {; Processes using fungi}
- 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)
- 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
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}
- C12R: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS

## Abstract

Antifungal compounds, an antifungal compound extracted from Epicoccum purpurascens, also known as Epicoccum nigrum, methods of producing the antifungal compounds, isolates and compositions comprising the antifungal compounds, and methods of using the antifungal compounds.

## Claims

### Claim 1

A method of treating or reducing risk of a fungal infection in a subject in need thereof comprising administering to said subject a composition comprising an effective amount of Epicoccum purpurascens strain SVB-F1 on deposit at the National Measurement Institute, Australia (NMI) under accession number V10/000331 or an extract, an exudate or isolate thereof, and an agriculturally or a pharmaceutically acceptable carrier wherein the carrier is a solid carrier.

### Claim 2

A method of treating or reducing risk of a fungal infection and/or infestation on a target surface in need thereof comprising applying to said target surface a composition comprising an effective amount of Epicoccum purpurascens strain SVB-F1 on deposit at the National Measurement Institute, Australia (NMI) under accession number V10/000331 or an extract, an exudate or isolate thereof, and an agriculturally or pharmaceutically acceptable carrier wherein the carrier is a solid carrier.

### Claim 3 (depends on 2)

The method of claim 2 wherein the fungal infection comprises infection by a filamentous fungus.

### Claim 4 (depends on 3)

The method of claim 3 wherein the fungus is
(a) of the family Gnomoniaceae, Cortiaceae, Magnoporthaceae, Mycosphaerellaceae, Pleosporaceae, Sclerotiniaceae, Typhulaceae, Valsaceae, or Venturiaceae;
(b) of the genus Apiognomonia, Alternaria, Botrytis, Botryotinia, Magnaporthe, Phomopsis, Rhizoctonia, Sclerotinia, Sclerotium, or Venturiaceae;
(c) Apiognomonia supraseptata, Alternaria alternata, Botrytis cinerea, Botryotinia spp., Magnaporthe grisea, Phomopsis viticola, Rhizoctonia solani, Sclerotinia sclerotiorum, Sclerotium cepivorumi, or Venturia inaequalis;
(d) of the family Dothioraceae, Trichosporonaceae, Piedraiaceae, Arthrodermataceae, Sphaeropsidaceae, or Microascaceae;
(e) of the genus Hortaea, Trichosporon, Piedraia, Trichophyton, Microsporum, Epidermophyton, Hendersonula, Scytalidium,or Scopulariiopsis;
or the fungal infection is selected from anthracnose, canker, ringspot disease, blight and lesions of vegetables, fruit rot, blast disease or bright disease, cane and leaf spot, damping off, wire stem, white mould, wilt or stalk rot, southern blight, and scab lesions.

### Claim 5 (depends on 2)

The method of claim 2 wherein the composition comprises a reproductively viable form and amount of Epicoccum purpurascens strain SVB-F1 on deposit at the National Measurement Institute, Australia (NMI) under accession number V10/000331.

### Claim 6 (depends on 2)

The method of claim 2 wherein the composition is formulated as a wettable powder, soluble powder, dust, granule, or water-dispersible granule.

### Claim 7 (depends on 2)

The method of claim 2 wherein the composition is a powder.

### Claim 8 (depends on 2)

The method of claim 2 wherein the carrier comprises one or more carriers for granules.

### Claim 9 (depends on 2)

The method of claim 2 wherein the carrier comprises one or more mineral earths selected from the group consisting of silicic acids, silica gels, silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, aluminas calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, and ammonium nitrate; one or more ureas; one or more vegetable products selected from the group consisting of grain meals; bark meal, wood meal and nutshell meal; one or more cellulosic powders; one or more crushed or fractionated natural rocks selected from the group consisting of calcite, marble, pumice, sepiolite and dolomite; one or more synthetic granules of inorganic or organic meals; one or more granules of organic material selected from the group consisting of sawdust, coconut shells, corn cobs, corn husks and tobacco stalks; kieselguhr; tricalcium phosphate; powdered cork; absorbent carbon black; one or more water soluble polymers, resins, or waxes or solid fertilizers, or a combination of any two or more thereof.

### Claim 10 (depends on 2)

A method of claim 2 wherein the carrier is talc.

### Claim 11 (depends on 2)

A method of claim 2 wherein the composition is formulated by mixing and/or milling the Epicoccum purpurascens strain or an exudate thereof with the agriculturally or pharmaceutically acceptable carrier.

### Claim 12 (depends on 4)

A method of claim 4 wherein the fungus is selected from
Apiognomonia supraseptata, Rhizoctonia solani, Magnaporthe grisea, Alternaria alternata, Botrytis cinerea, Sclerotinia sclerotiorum, Sclerotium cepivorumi, Phomopsis viticola, Venturia inaequalis,
Apiognomonia supraseptata, Alternaria alternata, Botrytis cinerea, Magnaporthe grisea, Phomopsis viticola, Rhizoctonia solani, Sclerotinia sclerotiorum, Sclerotium cepivorumi, Venturia inaequalis;
Hortaea werneckii, syn. Phaeoannellomyces werneckii, Trichosporon beigelii, Piedraia hortae, Trichophyton rubrum, Microsporum gypseum, Epidermophyton floccosum, Scytalidium dimidiatum, syn Hendersonula toruloidea, Scytalidium hyalinum, Scopulariopsis brevicaulis;
Hortaea werneckii, syn. Phaeoannellomyces werneckii, Trichosporon beigelii, Piedraia hortae, Trichophyton rubrum, Microsporum gypseum, Epidermophyton floccosum, Hendersonula toruloidea, Scytalidium hyalium, or Scopulariopsis brevicaulis;
or the fungal infection is selected from oak anthracnose, stem canker of tomato, ringspot disease of pear, parsley leaf blight, grey rot, noble rot of grapes, rice rotten neck, rice seedling blight, blast of rice, oval leaf spot of graminea, pitting disease, ryegrass blast, johnson spot, leaf and berry spot of grapes, damping off death of seedlings in agriculture, wire stem disease of cabbage, cauliflower and related plants, white mould in soy beans and dry edible beans, steam rot in canola, southern blight of wheat and tomato, or apple scab.

### Claim 13

A method of treating or reducing risk of a fungal infection and/or infestation on a target surface in need thereof comprising applying to said target surface a composition comprising an effective amount of Epicoccum purpurascens strain SVB-F1 on deposit at the National Measurement Institute, Australia (NMI) under accession number V10/000331 and an agriculturally or pharmaceutically acceptable carrier wherein the carrier is a solid carrier.

### Claim 14

A method of treating or reducing risk of a fungal infection and/or infestation on a target surface in need thereof comprising applying to said target surface a composition comprising an effective amount of Epicoccum purpurascens strain SVB-F1 on deposit at the National Measurement Institute, Australia (NMI) under accession number V10/000331 or an extract, an exudate or isolate thereof, and an agriculturally or pharmaceutically acceptable carrier wherein the carrier is a solid carrier and wherein the extract, exudate or isolate exhibits antifungal activity against:
(a) the family Gnomoniaceae, Cortiaceae, Magnoporthaceae, Mycosphaerellaceae, Pleosporaceae, Typhulaceae, Valsaceae, or Venturiaceae;
(b) the genus Apiognomonia, Alternaria, Botrytis, Botryotinia, Magnaporthe, Phomopsis, Rhizoctonia, Sclerotium, or Venturiaceae;
(c) Apiognomonia supraseptata, Alternaria alternata, Botrytis cinerea, Botryotinia spp., Magnaporthe grisea, Phomopsis viticola, Rhizoctonia solani, Sclerotinia sclerotiorum, Sclerotium cepivorumi, or Venturia inaequalis;
(d) the family Dothioraceae, Trichosporonaceae, Piedraiaceae, Arthrodermataceae, Sphaeropsidaceae, or Microascaceae; or
(e) the genus Hortaea, Trichosporon, Piedraia, Trichophyton, Microsporum, Epidermophyton, Hendersonula, Scytalidium, or Scopulariiopsis.