Methods for controlling plant pathogenic fungi using jasamicin

Abstract

This disclosure relates to a method for controlling or preventing plant pathogenic fungi on plants or their plant propagation material, the plant pathogenic fungi belonging to the genus *Cyclocarya paliurus*, *Bacillus oryzae*, *Cyclocarya argentea*, *Cyclocarya gleditsiae*, *Cyclocarya rotundifolia*, *Bacillus aubergine*, *Botrytis cinerea*, *Botrytis tulipta*, *Cercospora multiflora*, *Cercospora kikuchi*, and / or *Cercospora davidii*, the method comprising applying a composition containing jassamycin to the plant, its plant propagation material, or the site thereof.

Description

[0001] This invention relates to a method for controlling plant pathogenic fungi using jasamicin. Background Technology

[0002] Jassamycin is a natural compound, designated FR-900848, produced by bacteria of the genera *Streptoverticillium* or *Streptomyces*. This compound was first discovered in 1990 by Yoshida et al. (1990), *Journal of Antibiotics*, pp. 748-754. Yoshida et al. (1990) disclosed that this compound is active against species of *Aspergillus niger*, *Mucorrouxianaus*, *Aureobasidium*, *Penicillium chrysogenum*, *Fusarium oxysporum*, *Sclerotinia arachidis*, and *Trichophyton*.

[0003] JP2101006 discloses that jassamycin is active against Alternaria leaf spot and Botrytis gray mold.

[0004] Fu et al. (2020), Nature Communications 11-3387, disclosed that jassamycin is active against some yeasts, fungi such as Aspergillus species, Fusarium oxysporum species, Sedospora species, and some Mucorales fungi. Fu et al. (1990) indicated that jassamycin would have broad-spectrum fungicidal activity; however, they did not teach or imply which fungi were affected, nor did they teach or imply which plants would have fungicidal activity against jassamycin.

[0005] Due to the development of resistance in plant pathogenic fungi to known pesticides, government regulations, and social pressure, there remains a demand for improved products or bio-based compounds with activity against plant pathogenic fungi. Summary of the Invention

[0006] This invention relates to a method for controlling or preventing plant pathogenic fungi on plants or their plant propagation material, the plant pathogenic fungi belonging to the following species: *Glomerella lagenarium*, *Magnaporthegrisea*, *Mycosphaerella arachidis*, *Phaeosphaerianodorum*, *Pyrenophora teres*, *Venturia inaequalis*, *Botrytis eliptica*, *Botrytis tulipae*, *Corynesporacassiicola*, *Cercospora kikuchii*, and / or *Cercospora sojina*, the method comprising applying a composition containing jasamcinol to the plant, its plant propagation material, or the site thereof.

[0007] On the other hand, the present invention relates to the use of jasamicin for the control or prevention of plant pathogenic fungi, wherein the fungi are selected from *Trichophyton cucumeris*, *Bacillus riceis*, *Cyclocarya paliurus*, *Cyclocarya gleditsiae*, *Cyclocarya rotundifolia*, *Aureobasidium elutum*, *Botrytis cinerea*, *Botrytis tulipta*, *Cercospora multipathata*, *Cercospora kikuchi*, and *Cercospora davidii*. Detailed Implementation

[0008] A method for controlling or preventing plant pathogenic fungi on plants or their plant propagation material, the plant pathogenic fungi belonging to the following species: *Trichophyton cucumeris*, *Blastomyces oryzae*, *Cyclocarya paliurus*, *Cyclocarya gleditsiae*, *Cyclocarya rotundifolia*, *Aureobasidium maculata*, *Botrytis cinerea*, *Botrytis tulipta*, *Cercospora multiflora*, *Cercospora kikuchi*, and / or *Cercospora davidii*, the method comprising applying to the plant, its plant propagation material, or its location a composition comprising jaxamycin, preferably a fungicide-effective amount of jaxamycin.

[0009] The term "effective fungicide amount" as used refers to the amount of one or more compounds, or combinations thereof, that can affect fungal growth. Control or alteration of effects includes all deviations from natural development, such as killing, inhibiting, etc., and prevention includes forming barriers or other defenses within or on the plant to prevent fungal infection. Control or prevention means reducing the infection of plant pathogenic fungi to a level that has been proven to be improved. An effective fungicide amount of jasamicin contains 0.1 to 500 ppm, preferably 0.5 to 250 ppm of jasamicin.

[0010] Surprisingly, gasarmycin was found to be effective in controlling fungi such as *Parastagonospora cucumeris*, *Bacillus oryzae*, *Gnaphalium affine*, *Parastagonospora nodorum*, *Parastagonospora rotundifolia*, *Aureobasidium majus*, *Botrytis cinerea*, *Botrytis tulipta*, *Cercospora multipathata*, *Cercospora kikuchi*, and / or *Cercospora davidii*. Therefore, gasarmycin exhibits unexpected fungicidal activity against these fungi.

[0011] Conversely, we found that jasamcinol exhibited very little or no activity against oomycetes (e.g., *Phytophthora infestans*, *Pythium ultimum*, and *Plasmopora viticola*), basidiomycetes (e.g., *Puccinia recondita* and *Rhizoctonia solani* (synonym: *Thanatephorus cucumeris*)), and ascomycetes (*Blumeria graminis* and *Uncinula necator*). Therefore, it appears that the teachings of Fu, Y. et al. in *Nat Commun* [Nature Communications] 11, 3387 (2020) do not apply to all fungi.

[0012] Jaxamycin is a known compound and has the structural formula according to formula (Ia).

[0013] (Ia)

[0014] Jaxamycin having formula (Ia) is a natural product containing oligocyclopropyl groups, also known as FR-900848. Jaxamycin is a polyketide containing 5'-amino-5'-deoxy-3,4,5,6-tetrahydrouridine, wherein one hydrogen atom of the amino group is replaced by (1E,3E)-1-[(1R,1'R,1''R,1'''R,2S,2'R,2''R,2'''S)-2'''-{(E)-2-[(1R,2R)-2-methylcyclopropyl]vinyl}[1,1':2',1'':2'',1'''-tetra(cyclopropane)]-2-yl]-5-oxopent-1,3-dien-5-yl groups.

[0015] The structure of jasamicin is C. 32 H 43 N3O6 contains 5'-amino-5'-deoxy-5,6-dihydrouridine and an unsaturated fatty acid comprising four tandem and one separate cyclopropane ring.

[0016] The IUPAC name for jasamicin is (2E,4E)-N-[[(2R,3S,4R,5R)-5-(2,4-dioxo-1,3-hexahydropyridazin-1-yl)-3,4-dihydroxyoxacyclopentan-2-yl]methyl]-5-[(1S,2R)-2-[(1R,2R)-2-[(1R,2R)-2-[(1R,2S)-2-[(E)-2-[(1R,2R)-2-methylcyclopropyl]vinyl]cyclopropyl]cyclopropyl]cyclopropyl]cyclopropyl]cyclopropyl]cyclopropyl]pent-2,4-dieneamide.

[0017] Although A. Barrett et al., J. Am. Chem. Soc. [Journal of the American Chemical Society] 1996, 118, 45, 11030–11037 disclosed a total synthesis method for jasamcinol entitled “pentacyclopropaneantifungal agent FR-900848”, the accessible and usable compound is preferably obtained or isolated from bacteria of the genus Streptomyces.

[0018] Microorganisms expressing compounds according to formula (Ia) may be Streptoverticillium and / or Streptomyces, preferably Streptoverticillium fervens and / or Streptomyces luteoverticillatus, or their spores, because these microorganisms express compounds of formula (Ia) as metabolites.

[0019] A particularly suitable route for producing jaxamycin could be by culturing *Streptococcus thermophilus* and isolating jaxamycin, for example, according to the method disclosed by Masaru et al., *Journal of Antibiotics*, 1990, Vol. 43, No. 7, pp. 748-754.

[0020] The homologues of jasamicin are compounds Ib and Ic based on the following formula: (Ib); and

[0021] (Ic),

[0022] These homologues according to formulas Ib) and Ic) are expressed by the above-mentioned microbial cultures in different but usually small or negligible amounts.

[0023] The method according to the invention involves applying a composition containing jaxamycin to a plant, its propagating material, or its location. Jaxamycin can be applied to the plant by spraying, dusting, or any suitable other means.

[0024] A suitable method for controlling or preventing crop plant infection by *Microcystis suis*, *Blastomyces oryzae*, *Cyclocarya paliurus*, *Cyclocarya gleditsiae*, *Cyclocarya rotundifolia*, *Agrostis spp.*, *Botrytis cinerea*, *Botrytis tulipta*, *Cercospora multiflora*, *Cercospora kikuchi*, and / or *Cercospora sacchari* includes the application of an agricultural chemical composition containing jasamcinol, by foliar application. The frequency and rate of application will depend on the risk of infection by plant pathogenic fungi. However, jasamcinol can also be absorbed through the roots via the soil by wetting the plant site with a liquid formulation or by applying the compound in solid form, such as in granular form, to the soil (soil application).

[0025] Compositions containing jaxamycin can be used as seed dressings to treat plant propagation material, such as seeds, fruits, tubers, or grains, or plant cuttings, to protect them from infection by *Microcystis suis*, *Bacillus rice*, *Cercospora argentea*, *Cercospora glomerata*, *Cercospora rotundifolia*, *Botrytis cinerea*, *Botrytis ulmiformis*, *Botrytis tulipta*, *Cercospora multiflora*, *Cercospora kikuchi*, and / or *Cercospora davidii*. Propagation material can be treated with compositions containing jaxamycin before planting: for example, seed dressing can be applied before sowing. Jaxamycin can also be applied to grains (coating) by soaking seeds in a liquid formulation or by coating them with a solid formulation. The composition can also be applied to the planting site when planting propagation material, such as by applying it to the furrows of the seeds during sowing.

[0026] The method according to the invention includes applying a composition, wherein the composition may be used in any conventional form, for example, as a double-packaged powder for dry seed treatment (DS), an emulsion for seed treatment (ES), a flowable concentrate for seed treatment (FS), a solution for seed treatment (LS), a water-dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspension emulsion (SE), a capsule suspension (CS), water-dispersible particles (WG), emulsifiable particles (EG), a water-in-oil emulsion (EO), an oil-in-water emulsion (EW), a microemulsion (ME), an oil dispersant (OD), an oil suspension (OF), an oil-soluble liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical grade (TK), a dispersible concentrate (DC), a wettable powder (WP), or any technically feasible formulation in combination with agriculturally acceptable adjuvants. Such compositions can be produced in conventional ways, for example by mixing the active ingredient with at least one suitable inert formulation adjuvant (e.g., diluent, solvent, filler, and optionally, other formulation ingredients such as surfactants, biocides, antifreeze agents, adhesives, thickeners, and compounds that provide adjuvant effects). Conventional sustained-release formulations designed for long-term sustained efficacy can also be used. In particular, formulations intended for spray application, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, may contain surfactants such as wetting agents and dispersants, and other compounds that provide adjuvant effects, such as condensation products of formaldehyde and naphthalene sulfonates, alkyl aryl sulfonates, lignin sulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0027] Treatment can be applied to any suitable plant to prevent or control infection by *Cercospora cucumeris*, *Bacillus rice*, *Cercospora argentea*, *Cercospora glomerata*, *Cercospora rotundifolia*, *Botrytis cinerea*, *Botrytis tulipta*, *Cercospora multiflora*, *Cercospora kikuchi*, and / or *Cercospora saccharifolia*. Suitable plants include ornamental plants (such as trees, shrubs, flowers, and houseplants), as well as fruits, vegetables, herbs, and forage. Preferably, the plants are selected from vegetables (such as cucumbers and tomatoes), fruits (such as apples, pears, and grapes), and cereals (such as barley, wheat, corn, peanuts, rice, and soybeans).

[0028] The plants used in the methods for controlling or preventing *Trichophyton cucumeris* infection disclosed herein include cucumber. *Trichophyton cucumeris* is effectively controlled at fungicide concentrations of 0.1 ppm to 500 ppm, preferably 0.2 ppm to 300 ppm, and preferably 0.3 ppm to 200 ppm.

[0029] The plant used in the methods for controlling or preventing rice blast fungus infection disclosed herein includes or is rice. At fungicide-effective amounts of jaxamycin, from 1 ppm to 500 ppm, preferably 2 ppm to 300 ppm, and preferably 5 ppm to 200 ppm, the rice blast fungus is unexpectedly effectively controlled.

[0030] The plant used in the methods for controlling or preventing *Gnaphalium arachidii* infection disclosed herein includes or is peanut. At fungicide-effective amounts of jasamicin, from 20 ppm to 500 ppm, preferably 30 ppm to 300 ppm, and preferably 40 ppm to 250 ppm, *Gnaphalium arachidii* on plants is unexpectedly effectively controlled.

[0031] The plants used in the methods for controlling or preventing *Cyclocarya rotundifolia* infection disclosed herein include barley. *Cyclocarya rotundifolia* is unexpectedly effectively controlled at fungicide levels of 0.5 ppm to 500 ppm, preferably 1 ppm to 300 ppm, and preferably 2 ppm to 200 ppm.

[0032] The plant used in the methods for controlling or preventing apple scab infection disclosed herein includes or is a fruit, preferably apple. At fungicide-effective amounts of jassamycin, from 0.1 ppm to 500 ppm, preferably 0.2 ppm to 300 ppm, and preferably 0.3 ppm to 200 ppm, apple scab is unexpectedly effectively controlled.

[0033] The plants used in the methods for controlling or preventing *Dendrocalamus gleditsiae* infection disclosed herein include wheat. *Dendrocalamus gleditsiae* is effectively controlled at fungicide concentrations of 50 to 500 ppm, preferably 60 to 400 ppm, of jasamcinolone.

[0034] The term "plant" refers to all the tangible parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, culms, leaves, and fruits.

[0035] The term "useful plants" as used herein also includes useful plants. The term "useful plants" should be understood to also include useful plants that have been conferred herbicide tolerance.

[0036] The term “useful plant” should be understood to also include useful plants that have been transformed by the use of recombinant DNA technology to enable them to synthesize one or more selectively acting toxins, such as those known to come from toxin-producing bacteria, especially those of the genus Bacillus.

[0037] The term "plant propagation material" should be understood to refer to the reproductive parts of a plant, such as seeds, which can be used for plant propagation, as well as vegetarian material, such as cuttings or tubers (e.g., potatoes). References may include, for example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts of the plant. References may also include germinating plants and young plants that will be transplanted after germination or emergence. These young plants may be protected before transplanting by complete or partial treatment with maceration. Preferably, "plant propagation material" should be understood to mean seeds.

[0038] In one embodiment, the composition containing jaxamycin is an agriculturally acceptable composition.

[0039] As used herein, the term "site" means the place in which or on which a plant grows, or the place where the seeds of a cultivated plant are sown, or the place where the seeds will be placed in the soil. It includes soil, seeds, and seedlings, together with the established vegetation.

[0040] Throughout this document, the term “composition” refers to various mixtures or combinations of jaxamycin, such as in the form of a single “ready-mix”, in a combined spray mixture (which consists of formulations of separate single active ingredient components) (e.g., a “tank-mix”), and when used in a sequential manner (i.e., one after another over a suitably short period of time, such as hours or days).

[0041] The composition containing jaxamycin in the method according to the invention is preferably an agriculturally acceptable composition. Preferably, the composition further comprises at least one agriculturally acceptable carrier, additive, formulation adjuvant, and / or surfactant.

[0042] Suitable carriers and adjuvants, for example for agricultural use, can be solid or liquid and are useful in formulation techniques, such as natural or recycled minerals, solvents, dispersions, wetting agents, thickeners, binders or fertilizers.

[0043] In another embodiment, the composition comprises one or more additional bioactive compounds, preferably one or more additional pest control agents, such as fungicides, insecticides, or herbicides.

[0044] One or more such additional pest-killing components are known and are mentioned above by their so-called ISO common names or their IUPAC names. Typical pest-killing components are included in the UK Crop Production Council's online Pesticide Manual ("E-pesticideManual") and Alan Wood's Compendium of Pesticide Common Names.

[0045] In one embodiment of the method according to the invention, jaxamycin is applied at a rate of 5 to 2000 g ai / ha, particularly 1 to 1000 g ai / ha, preferably 5 to 500 g ai / ha, and more preferably 1 to 250 g ai / ha. As used herein, the abbreviation “ai” stands for “active ingredient,” and the active ingredient comprises or is jaxamycin.

[0046] In another embodiment of the method according to the invention, jaxamycin is applied at a rate of 0.001 to 50 g ai per kg of plant propagation material (particularly per kg of seeds). Preferably, jaxamycin is applied at a rate of 0.01 to 40 g ai / kg of plant propagation material, and more preferably at a rate of 0.1 to 30 g ai / kg of plant propagation material.

[0047] The present invention also relates to the use of jasamicin for the control or prevention of plant pathogenic fungi, wherein the fungi are selected from *Trichophyton cucumeris*, *Blastomyces oryzae*, *Gnaphalium argentea*, *Gnaphalium glomeratum*, *Gnaphalium rotundifolium*, *Gnaphalium argentea*, *Gnaphalium argentea*, *Botrytis cinerea*, *Botrytis tulipta*, *Cercospora multiflora*, *Cercospora kikuchi*, and *Cercospora davidii*.

[0048] Preferably, the use of jasamicin for the control or prevention of plant pathogenic fungi is on plants or on plant propagation material. The methods and uses according to the invention do not include methods and uses for treating human or animal bodies by surgery or therapy. Example

[0049] Materials and Methods

[0050] The jasamicin used in this example was produced by culturing *Streptococcus thermophilus* and isolating jasamicin according to the method disclosed by Masaru et al., *Journal of Antibiotics*, 1990, Vol. 43, No. 7, pp. 748-754.

[0051] Example 1. In vitro liquid culture assay.

[0052] Conidia or mycelial fragments from the fungi / oomycetes listed in Table 1 were mixed into nutrient broth (Potato Dextrose Broth (PDB) / Vogel's basal medium (Microbial Genetics Bulletin [Microbial Genetics Bulletin] 13:42-43, 1956)). 10 µL of a solution of jaxamycin and DMSO was dispensed into the wells of a 96-well microtiter plate, followed by adding 90 µL of nutrient broth containing conidia or mycelial fragments to the wells. The plate was then incubated at 24°C and evaluated spectrophotometrically at 620 nm after 2 to 7 days. The efficacy of jaxamycin was assessed by comparing the test wells with untreated inoculated and uninoculated wells and allocating efficacy on a 0–100% scale.

[0053] The results in Table 1 show that, in liquid culture assays, *Botrytis cinerea*, *Botrytis tulipta*, *Cercospora multiflora*, *Cercospora kikuchi*, *Cercospora davidii*, *Microcystis cucurbita*, and *Cercospora arachifolia* were effectively controlled by jaxamycin. However, jaxamycin did not affect the growth of *Pythium cerevisiae* and *Rhizoctonia solani*.

[0054] Table 1. Efficacy (%) of different concentrations of jaxamycin against fungal and oomycete species in liquid culture assays.

[0055]

[0056] Example 2. Efficacy of jasamicin against fungi and oomycetes in leaf disc assays.

[0057] Leaf disc determination

[0058] The efficacy of leaf discs was assessed on a 0-100% scale by comparing test discs with untreated inoculated leaf discs (representing 0% control) and leaf discs treated with a known standard that completely controls the pathogen (representing 100% control).

[0059] Phytophthora (late blight of potato / tomato):

[0060] Tomato leaf discs were placed on water agar in a 24-well plate and sprayed with the test solution. After drying, the leaf discs were inoculated with a suspension of fungal spores. After appropriate incubation, the activity of the compound was assessed at 4 dpi (days after inoculation) as prophylactic fungicidal activity. Dosage range: 200-22 ppm.

[0061] Grape downy mildew fungus (grape downy mildew):

[0062] Grapevine leaf discs were placed on agar in a 24-well plate and sprayed with the test solution. After drying, the leaf discs were inoculated with a suspension of fungal spores. After appropriate incubation, the activity of the compound was assessed at 7 dpi (days after inoculation) as prophylactic fungicidal activity. Dosage range: 200-22 ppm.

[0063] Blumeria graminis f.sp. tritici (wheat powdery mildew):

[0064] Barley leaf segments were placed on agar in a 24-well plate and sprayed with the test solution. After drying, leaf discs were inoculated with fungal spores. After appropriate incubation, the activity of the compound was assessed at 7 dpi (days after inoculation) as prophylactic fungicidal activity. Dosage range: 66-22 ppm.

[0065] Round-crystal lumenus (reticulate disease):

[0066] Barley leaf segments were placed on agar in a 24-well plate and sprayed with the test solution. After drying, leaf discs were inoculated with a suspension of fungal spores. After appropriate incubation, the activity of the compound was assessed at 4 dpi (days after inoculation) as prophylactic fungicidal activity. Dosage range: 200-22 ppm.

[0067] Hidden stalk rust fungus (brown rust):

[0068] Wheat leaf segments were placed on agar in a multi-well plate (24-well size) and sprayed with the test solution. After drying, the leaf discs were inoculated with a suspension of fungal spores. After appropriate incubation, the activity of the compound was assessed at 8 dpi (days after inoculation) as prophylactic fungicidal activity. Dosage range: 200-22 ppm.

[0069] *Gynostemma pentaphyllum* (synonym: *Gynostemma pentaphyllum*, glume blight):

[0070] Wheat leaf segments were placed on agar in a multi-well plate (24-well size) and sprayed with the test solution. After drying, the leaf discs were inoculated with a suspension of fungal spores. After appropriate incubation, the activity of the compound was assessed at 4 dpi (days after inoculation) as prophylactic fungicidal activity. Dosage range: 200-22 ppm.

[0071] Rice blast fungus (Magnaporthe oryzae) (rice blast disease):

[0072] Rice leaf segments were placed on agar in a 24-well plate and sprayed with the test solution. After drying, the leaf discs were inoculated with a suspension of fungal spores. After appropriate incubation, the activity of the compound was assessed at 5 dpi (days after inoculation) as prophylactic fungicidal activity. Dosage range: 200-22 ppm.

[0073] The results in Table 2 show that jasamcinol showed activity against Ascomycetes rotundiformis, Ascomycetes glomerulosae, and Ascomycetes blast fungi in leaf disc assays, but no activity against Ascomycetes powdery mildew fungi and Basidiomycetes cryptidus rust fungi, and no activity against Oomycetes.

[0074] Table 2. Efficacy (%) of jasamicin against several fungi and oomycetes in leaf disc assays.

[0075]

[0076] Example 3. Efficacy of Jaxamycin against fungi and oomycetes on plants.

[0077] Whole plant testing

[0078] Whole-plant disease efficacy was assessed by comparing symptom coverage on plants and scoring it on a 0-100% scale. Plants were compared to untreated control plants and plants treated with standards having complete control (serving as examples of 100% coverage).

[0079] The wheat-specific form of Blumeria graminis f. sp. on wheat. (tritici / Erysiphe graminis f. sp. tritici) is applied preventively.

[0080] In a spraying chamber, one-week-old wheat cultivars of the variety Arina were sprayed with a test compound diluted in water. Two days after application, the test plants were inoculated in an inoculation chamber by dispersing powdery mildew spores. The inoculated test plants were incubated in a greenhouse at 20°C / 18°C (day / night) and 60% rh (relative humidity), and the percentage of leaf area covered by the disease was assessed when an appropriate level of disease appeared on untreated control plants (7–9 days after application).

[0081] Preventative application of Colletotrichum lagenarium (a fungus that causes cucurbit anthracnose) to cucumbers.

[0082] In a spray chamber, 1-week-old cucumber cultivar Wisconsin was sprayed with a test compound diluted in water. One day after application, the test plants were inoculated by spraying them with a spore suspension. After a 30-h incubation period at 23°C and 100% rh in the dark, the inoculated test plants were kept in a greenhouse at 23°C / 21°C (day / night) and 70% rh. The percentage of leaf area covered by disease was assessed when an appropriate level of disease appeared on untreated control plants (6–8 days after application).

[0083] Preventive application of the rice blast fungus (Magnaporthe grisea / Pyricularia oryzae) to rice.

[0084] In a spray chamber, 3-week-old rice cultivars of the Koshihikari variety were sprayed with a test compound diluted in water. Two days after application, the test plants were inoculated by spraying them with a spore suspension. The inoculated test plants were incubated at 25°C and 95% rh, and the percentage of leaf area covered by disease was assessed when an appropriate level of disease appeared on untreated control plants (7–9 days after application).

[0085] Preventative application of Cercospora arachidicola to peanuts.

[0086] In a spray chamber, 3-week-old peanut cultivar Georgia Green was sprayed with a test compound diluted in water. One day after application, the test plants were inoculated by spraying the leaf surfaces below them with a spore suspension. After a 4-day incubation period under a plastic cover at 23°C and 100% rh, the inoculated test plants were maintained in a greenhouse at 23°C / 20°C (day / night) and 70% rh. The percentage of leaf area covered by disease was assessed when an appropriate level of disease appeared on untreated control plants (12–14 days after application).

[0087] Preventative application of Phytophthora infestans to potatoes.

[0088] In a spray chamber, 2-week-old potato cultivars of the Bintje variety were sprayed with a test compound diluted in water. Two days after application, the test plants were inoculated by spraying them with a sporangium suspension. The inoculated test plants were then incubated in a growth chamber at 18°C ​​with 14 h light / day and 100% rh, and the percentage of leaf area covered by disease was assessed when an appropriate level of disease appeared on untreated control plants (5–7 days after application).

[0089] Preventative application of fungi that cause grape downy mildew on grapes.

[0090] In a spray chamber, 5-week-old grape seedlings of the cultivar Gutedel were sprayed with a test compound diluted in water. One day after application, test plants were inoculated by spraying the leaf surfaces below the seedlings with a sporangium suspension. The inoculated test plants were then incubated in a greenhouse at 22°C and 100% rh, and the percentage of leaf area covered by disease was assessed when an appropriate level of disease appeared on untreated control plants (6–8 days after application).

[0091] Preventative application of Puccinia recondita f. sp. tritici, a type of rust fungus found on wheat.

[0092] In a spray chamber, 2-week-old wheat cultivars of the variety Arina were sprayed with a test compound diluted in water. One day after application, the test plants were inoculated by spraying them with a spore suspension. After a 1-day incubation period at 20°C and 95% rh, the inoculated test plants were maintained in a greenhouse at 20°C / 18°C (day / night) and 60% rh. The percentage of leaf area covered by disease was assessed when an appropriate level of disease appeared on untreated control plants (12–14 days after application).

[0093] Preventive application of Helminthosporium teres to barley.

[0094] In a spray chamber, 1-week-old barley cultivars of Regina were sprayed with a test compound diluted in water. Two days after application, the test plants were inoculated by spraying them with a spore suspension. The inoculated test plants were incubated at 20°C and 95% rh, and the percentage of leaf area covered by disease was assessed when an appropriate level of disease appeared on untreated control plants (5–7 days after application).

[0095] Preventative application of fungus scab on apples.

[0096] In a spray chamber, 3-week-old apple seedlings were sprayed with a test compound diluted in water. One day after application, the test plants were inoculated by spraying them with a spore suspension. After a 2-day incubation period at 20°C and 95% rh, the inoculated test plants were placed in a greenhouse at 20°C / 19°C (day / night) and 60% rh. The percentage of leaf area covered by disease was assessed when an appropriate level of disease appeared on untreated control plants (11–13 days after application).

[0097] Preventative application of *Hylocereus undatus* to grapes.

[0098] In a spray chamber, 5-week-old grape seedlings of the cultivar Gutedel were sprayed with a test compound diluted in water. One day after application, test plants were inoculated by shaking plants infected with grape powdery mildew. The inoculated test plants were incubated under a 14 / 10 h (light / dark) light scheme at 24°C / 22°C (day / night) and 70% rh, and the percentage of leaf area covered by the disease was assessed when an appropriate level of disease appeared on untreated control plants (7–9 days after application).

[0099] The results in Table 3 show that, as indicated, jasamicin exhibits surprisingly effective fungicidal activity against *Cyclocarya paliurus*, *Cyclocarya arachinensis*, *Acer macrantha*, *Cyclocarya cucumeroides*, and *Bacillus oryzae* on plants, but no activity was found against *Agromycetes* (wheat powdery mildew and *Agromycetes spp.), *Agromycetes* (basidiomycetes), *Agromycetes* (pathogenic *Phytophthora* and *Phytophthora*), and *Phytophthora* (grape downy mildew).

[0100] Table 3. Efficacy of Jaxamycin against Fungi and Oomycetes (%)

[0101] .

Claims

1. A method for controlling or preventing plant pathogenic fungi on plants or their plant propagation material, said plant pathogenic fungi belonging to the following species: *Microcystis cucumeris*, *Blastomyces oryzae*, *Cyclocarya paliurus*, *Cyclocarya gleditsiae*, *Cyclocarya rotundifolia*, *Aureobasidium maculata*, *Botrytis cinerea*, *Botrytis tulipta*, *Cercospora multiflora*, *Cercospora kikuchi*, and / or *Cercospora davidii*, said method comprising applying a composition containing jassamycin to said plant, its plant propagation material, or its location.

2. The method according to claim 1, wherein the composition comprises a fungicide-effective amount of jasamicin.

3. The method according to claim 1 or 2, wherein the plant is selected from vegetables such as cucumbers and tomatoes, fruits such as apples, pears and grapes, grains such as barley, wheat, or corn, peanuts, rice and soybeans.

4. The method according to any one of claims 1 to 3, wherein the composition is an agriculturally acceptable composition.

5. The method according to any one of claims 1 to 4, wherein the composition further comprises at least one agriculturally acceptable carrier, additive, formulation adjuvant, and / or surfactant.

6. The method according to any one of claims 1 to 5, wherein the composition comprises one or more additional bioactive compounds, preferably one or more additional pest control agents, such as fungicides, insecticides, or herbicides.

7. The method according to any one of claims 1 to 6, wherein the fungicide effective amount of jasamicin comprises 5 g ai / ha to 2000 g ai / ha.

8. The method according to any one of claims 1 to 6, wherein the effective amount of jasamicin for fungicide control comprises 0.001 to 50 g ai per kg of plant propagation material, preferably per kg of seeds.

9. Use of jasamicin for the control or prevention of plant pathogenic fungi, wherein the fungi are selected from *Trichophyton cucumeris*, *Blastomyces oryzae*, *Cyclocarya paliurus*, *Cyclocarya paliurus*, *Cyclocarya rotundifolia*, *Acer macrantha*, *Botrytis cinerea*, *Botrytis tulipta*, *Cercospora multipathata*, *Cercospora kikuchi*, and *Cercospora davidii*.

10. The use according to claim 9, wherein the control or prevention of plant pathogenic fungi is on plants or on plant propagation material.

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