USE OF AN AMPHIDINOL FOR ITS FUNGICIDAL AND/OR BACTERICIDAL ACTIVITY ON FUNGI, OOMYCETES AND/OR PATHOGENIC BACTERIA OF PLANTS AND CROP SEEDS

Abstract

Use of the molecule with the following formula (I) for its fungicidal and/or bactericidal activity on fungi, oomycetes and/or pathogenic bacteria of plants and crop seeds.

##STR00001##

Claims

1. Use of the molecule of the following formula (I): ##STR00016## wherein: R.sub.1 is selected from the group consisting of: ##STR00017## where: R.sub.3 represents H or SO.sub.3Na, R.sub.4 is H or OH, represents a single or double bond, n is equal to 0 or 1 and m is 0 or 1; and R.sub.2 is selected from the group consisting of: ##STR00018## for its fungicidal and/or bactericidal activity on fungi, oomycetes and/or pathogenic bacteria in plants and seeds.

2. Use according to claim 1 wherein R1 is: ##STR00019## wherein R.sub.3 is H or SO.sub.3Na.

3. Use according to claim 1 or 2, wherein R2 is: ##STR00020##

4. Use according to any one of the preceding claims, wherein the molecule of formula (I) is amphidinol 18: ##STR00021##

5. Use according to any one of the preceding claims, wherein the molecule of formula (I) is extracted from cells of one or more microalgae of the genus Amphidinium.

6. Use according to claim 5 wherein the molecule of formula (I) is extracted from Amphidinium carterae cells.

7. Use according to any one of the preceding claims, wherein said pathogenic fungi of plants and seeds are pathogenic fungi of plants and seeds of the genera Fusarium, Colletotrichum, Mycosphaerella, Phytophthora and Alternaria, preferably fungi vs. pairs. cultured plants Triticum sativum/Mycosphaerella graminicola—Triticum sativum/Fusarium graminearum—Solanum tuberosum/Phytophtora infestans—Vinis vitifera/Plasmospora viticola—Vinis vitifera/Erysiphe necator—Lycopersicon esculentum/Phytophtora infestans.

8. Use according to claim 7 wherein said pathogenic fungi of crop plants and seeds of the genera Fusarium, Colletotrichum, Mycosphaerella, Phytophthora and Alternaria are selected from the group consisting of Fusarium oxysporum, Fusarium solani, Fusarium avenaceum, Fusarium culmorum, Fusarium graminearum, Fusarium monihforme, Fusarium poae, Fusarium proliferatum, Fusarium sporotrichioides, Fusarium subglutinans, Fusarium tricinctum, Colletotrichum acutatum, Colletotrichum graminicola, Colletotrichum coffeanum, Colletotrichum gloeosporioides, Mycosphaerella graminicola, Phytophthora infestans, Alternaria solani and Alternaria brassisicola.

9. Use of the molecule of formula (I) according to any one of the preceding claims in an amount between 0.1 and 5 mg/mL, preferably between 0.5 and 3 mg/mL, particularly preferably between 0.75 and 1 mg/mL.

10. A process for controlling crop plant and seed pathogenic fungi, oomycetes and/or bacteria comprising applying to the crop plants and/or coating said seeds with: ##STR00022## wherein: R.sub.1 is selected from the group consisting of: ##STR00023## where: R.sub.3 represents H or SO.sub.3Na, R.sub.4 is H or OH, represents a single or double bond, n is equal to 0 or 1 and m is 0 or 1; and R.sub.2 is selected from the group consisting of: ##STR00024##

11. Control process according to claim 10, curative or preventive.

12. Control process according to claim 10 or 11, the molecule of formula (I) being applied at a dose between 0.1 and 5 mg/mL, preferably between 0.5 and 3 mg/mL, particularly preferrably between 0.75 and 1 mg/mL.

Description

FIGURE LEGENDS

[0047] FIG. 1. Fractionation of extract D on reversed-phase C18 column and activity test of the different fractions of extract D obtained by HPLC

[0048] A. In vitro test of F. graminearum growth inhibition by extract D at 5 g/L obtained after methanol extraction

[0049] B. Liquid chromatogram obtained after injection of extract D. The samples were assembled according to the dotted lines to form 5 fractions, denoted F1 to F5.

[0050] C. In vitro test of F. graminearum growth inhibition by fractions F1 to F5 at a concentration of 5 g/L

[0051] D. In vitro test of F. graminearum growth inhibition by fraction F1 at a concentration of 0.5 g/L, 0.75 g/L, 1 g/L, 1.5 g/L, 2.5 g/L, and 5 g/L

[0052] −: negative control: spores are incubated in the presence of the buffer alone

[0053] FIG. 2: Fractionation of fraction F1 on reversed-phase C18 column and activity test of the different fractions obtained by HPLC

[0054] A. Liquid chromatogram obtained after injection of fraction F1. The samples were assembled according to the dotted lines to form 5 fractions, denoted F1-1 to F1-5.

[0055] B. In vitro test of F. graminearum growth inhibition by fractions F1 to F5 at a concentration of 5 g/L

[0056] C. In vitro test of F. graminearum growth inhibition by fraction F1-2 at concentrations ranging from 0.0005 g/L to 1 g/L

[0057] −: negative control: spores are incubated in the presence of the buffer alone

[0058] FIG. 3. Mass spectrometry analysis of fraction F1-2.

[0059] A. Mass spectrum acquired by positive-mode electrospray ionization on the molecule of interest collected F1-2

[0060] B. Tandem mass spectrum of the 1381.8276 Da ion detected in A. The circled peaks are consistent with those found in AM18 characterized by Nuzzo et al., 2014 (7)

[0061] FIG. 4. NMR analysis of fraction F1-2.

[0062] A. .sup.1H NMR spectrum (MeOD.sub.4 solvent) obtained for the molecule of fraction F1-2 derived from extract D

[0063] B. .sup.13C DEPT135 NMR spectrum (MeOD.sub.4 solvent) obtained for the molecule of fraction F1-2 derived from extract D

[0064] FIG. 5. Structural formula of the amphidinol 18 molecule, derived from fraction F1-2 of extract D

[0065] All COSY and TOCSY correlations between each of the protons are shown in bold.

DETAILED DESCRIPTION OF THE INVENTION

[0066] A first object of the invention relates to the use of the molecule of the following formula (I):

##STR00005##

[0067] wherein: [0068] R.sub.1 is selected from the group consisting of:

##STR00006##

[0069] where: [0070] R.sub.3 represents H or SO.sub.3Na, [0071] R.sub.4 is H or OH, [0072] represents a single or double bond, [0073] n is equal to 0 or 1 and [0074] m is 0 or 1; and [0075] R.sub.2 is selected from the group consisting of:

##STR00007##

[0076] for its fungicidal and/or bactericidal activity on fungi, oomycetes and/or pathogenic bacteria in plants and seeds.

[0077] Preferably, R1 is:

##STR00008##

[0078] wherein R.sub.3 is H or SO.sub.3Na.

[0079] Preferably, R2 is:

##STR00009##

[0080] Preferably, the molecule of formula (I) is amphidinol 18 or amphidinol 19:

##STR00010##

[0081] The molecule of formula (I) is an amphidinol.

[0082] The molecule of formula (I) can be synthetic or extracted from cells of one or more microalgae of the genus Amphidinium.

[0083] Amphidinium Species

[0084] Suitable Amphidinium species are selected from the group consisting of Amphidinium achromaticum, Amphidinium aculeatum, Amphidinium acutissimum, Amphidinium acutum, Amphidinium alinii, Amphidinium aloxalocium, Amphidinium amphidinioides, Amphidinium asymmetricum, Amphidinium aureum, Amphidinium belauense, Amphidinium bidentatum, Amphidinium bipes, Amphidinium boekhoutensis, Amphidinium boggayum, Amphidinium caerulescens, Amphidinium carbunculus, Amphidinium carterae, Amphidinium celestinum, Amphidinium chattonii, Amphidinium coeruleum, Amphidinium conradii, Amphidinium conus, Amphidinium coprosum, Amphidinium corallinum, Amphidinium corpulenturn, Amphidinium crassum, Amphidinium cristatum, Amphidinium cucurbita, Amphidinium cucurbitella, Amphidinium cupulatisquama, Amphidinium curvatum, Amphidinium cyaneoturbo, Amphidinium dentatum, Amphidinium discoidale, Amphidinium dubium, Amphidinium eilatiensis, Amphidinium emarginatum, Amphidinium fastigium, Amphidinium filum Bohm, Amphidinium flagellans, Amphidinium flexum, Amphidinium galbanurn, Amphidinium gibbosum, Amphidinium glaucovirescens, Amphidinium glaucum, Amphidinium globosum, Amphidinium hadai, Amphidinium herdmanii, Amphidinium incoloratum, Amphidinium inflaturn, Amphidinium kesselitzii, Amphidinium kesslitzii, Amphidinium klebsii, Amphidinium lacunarum, Amphidinium lanceolatum, Amphidinium lefevrei, Amphidinium lilloense, Amphidinium lissae, Amphidinium longum, Amphidinium luteum, Amphidinium machapungarum, Amphidinium macrocephalum, Amphidinium mammillatum, Amphidinium manannini, Amphidinium mananninii, Amphidinium massartii, Amphidinium mootonorum, Amphidinium mucicola, Amphidinium nasutum, Amphidinium obliquum, Amphidinium obrae, Amphidinium oceanicum, Amphidinium oculatum, Amphidinium operculatum, Amphidinium operculatum var. steinii, Amphidinium omithocephalum, Amphidinium ovoideum, Amphidinium ovum, Amphidinium pacificum, Amphidinium pelagicum, Amphidinium phthartum, Amphidinium psammophila, Amphidinium psittacus, Amphidinium purpureum, Amphidinium pusillum, Amphidinium rhynchocephalum, Amphidinium roseolum, Amphidinium ruttneri, Amphidinium salinum, Amphidinium schilleri, Amphidinium schroederi, Amphidinium scissum, Amphidinium sphagnicola, Amphidinium sphenoides, Amphidinium steinii, Amphidinium stellatum, Amphidinium stigmatum, Amphidinium sulcatum, Amphidinium tortum, Amphidinium trochodinioides, Amphidinium trochodinoides, Amphidinium trulla, Amphidinium truncatum, Amphidinium turbo, Amphidinium vernal, Amphidinium vigrense, Amphidinium vitreum, Amphidinium vittatum, Amphidinium wigrense, Amphidinium yoorugurrum, Amphidinium yuroogurrum.

[0085] Preferably, the molecule of formula (I) is extracted from Amphidinium carterae. There are several Amphidinium carterae strains in collection such as strains CCMP 124, 1314, 3177 (CCMP=Culture Collection of Marine Phytoplankton), AC 208, 792 (AC=Algobank Cean), BEA 01198 (BEA=Banco Espanol de Algas).

[0086] Advantageously, the Amphidinium carterae strain used according to the invention is CCM P 1314, AC208 or AC792.

[0087] Extraction

[0088] Said extract may be prepared by any cell extraction method known to the skilled person, solid-liquid or liquid-liquid, for example extraction in inorganic or organic solvent, which may be selected from the group consisting of water, aqueous solutions, hydrocarbon solvents (aliphatics, aromatics), oxygenated solvents (alcohols, ketones, acids, esters and ethers), halogenated solvents (dichloromethane, cholorforme) and mixtures in any miscible proportion thereof.

[0089] Advantageously, the preferred solvent will be water or oxygenated solvents, preferably alcohols, particularly preferably C1 to C4 alcohols such as methanol or ethanol.

[0090] Particularly preferably, C1 to C4 alcohols are preferred.

[0091] Preferably, said extract is a water-soluble fraction.

[0092] Concentration

[0093] Preferably, the molecule of formula (I) is used in an amount between 0.1 and 5 mg/mL, preferably between 0.5 and 3 mg/mL, particularly preferably between 0.75 and 1 mg/mL.

[0094] Mode of Action

[0095] Said fungicidal activity on crop plant and seed pathogenic fungi and/or oomycetes may be particularly exerted by inhibiting spore germination or by inhibiting fungal and/or oomycete growth.

[0096] The activity is exerted by cell wall and membrane lytic activity resulting in cell lysis.

[0097] Crop Plants

[0098] Said crop plants are in particular selected from the group consisting of cereals such as wheat, maize, barley, rice, soya, fruits and vegetables such as potato, carrot, apple trees, peach trees, apricot trees, tomatoes, radishes, beans, grapevine and ornamental plants.

[0099] Said crop plants are in particular selected from the group consisting of the genera Abelmoschus, Acacia, Achras, Agave, Agrostis, Aleurites, Allium, Anacardium, Ananas, Annona, Apium, Arachis, Areca, Armoracia, Arracacia, Artocarpus, Asparagus, Aspidosperma, Avena, Bertholletia, Beta, Boehmeria, Borassus, Brassica, Cajanus, Camellia, Cannabis, Capsicum, Carica, Carthamus, Carum, Carya, Castanea, Ceiba, Ceratonia, Chenopodium, Chrysanthemum, Cicer, Cichorium, Cinchona, Cinnamomum, Citrullus, Citrus, Cocos, Coffea, Cola, Colocasia, Corchorus, Corylus, Crotalaria, Cucumis, Cucurbita, Cydonia, Cymbopogon, Cynara, Dactylis, Daucus, Dioscorea, Diospyros, Echinochloa, Elaeis, Elettaria, Eleusine, Eragrostis, Eriobotrya, Eugenia, Fagopyrum, Ficus, Foeniculum, Fragaria, Furcraea, Glycine, Glycyrrhiza, Gossypium, Guizotia, Helianthus, Hevea, Hibiscus, Hordeum, Humulus, Ilex, Indigofera, Ipomoea, Jasminum, Juglans, Lactuca, Lagenaria, Lavandula, Lawsonia, Lens, Lepidium, Lespedeza, Linum, Litchi, Lolium, Lopmoea, Lotus, Lupinus, Lycopersicon, Lygeum, Macadamia, Malus, Mangifera, Manihot, Maranta, Medicago, Mentha, Mespilus, Metroxylon, Moringa, Musa, Myristica, Nicotiana, Olea, Onobrychis, Oryza, Panicum, Papaver, Pastinaca, Pelargonium, Pennisetum, Persea, Phaseolus, Phleum, Phoenix, Phormium, Pimpinella, Piper, Pistacia, Pisum, Prunus, Psidium, Punica, Pyrus, Raphanus Rheum, Ribes, Ricinus, Rose, Rubus, Saccharum, Scorzonera, Secale Sechium, Sesamum, Setaria, Solanum, Sorghum, Spinacia, Theobroma, Tragopogon, Trifolium, Trigonella, Triticum, Urena, Vaccinium, Valerianella, Vanilla, Vicia, Vigna, Vitellaria, Vitis, Xanthosoma, Zea, Zingiber.

[0100] Pathogens

[0101] Said crop plant and seed pathogenic fungi are ascomycetes or basidiomycetes, preferably ascomycetes.

[0102] Said crop plant and seed pathogenic fungi are fungi pathogenic to crop plants and seeds of the genera:

[0103] Acrocalymma, Acrocalymma medicaginis,

[0104] Fusarium, Fusarium affine, Fusarium arthrosporioides, Fusarium crookwellense, Fusarium culmorum, Fusarium graminearum, Fusarium moniliforme, Fusarium incarnatum, Fusarium solani, Fusarium langsethiae, Fusarium mangiferae, Fusarium oxysporum f. sp. albedinis, Fusarium oxysporum f. sp. asparagi, Fusarium oxysporum f. sp. batatas, Fusarium oxysporum f. sp. betae, Fusarium oxysporum f. sp. cannabis, Fusarium oxysporum f. sp. carthami, Fusarium oxysporum f. sp. cattleyae, Fusarium oxysporum f. sp. ciceris, Fusarium oxysporum f. sp. coffea, Fusarium oxysporum f. sp. cubense, Fusarium oxysporum f. sp. cyclaminis, Fusarium oxysporum f. sp. dianthi, Fusarium oxysporum f. sp. lentis, Fusarium oxysporum f. sp. lini, Fusarium oxysporum f. sp. lycopersici, Fusarium oxysporum f. sp. medicaginis, Fusarium oxysporum f. sp. pisi, Fusarium oxysporum f. sp. radicis-lycopersici, Fusarium oxysporum f. sp. spinacia, Fusarium oxysporum, Fusarium pallidoroseum, Fusarium patch, Fusarium proliferatum, Fusarium redolens, Fusarium sacchari, Fusarium solani, Fusarium subglutinans, Fusarium sulphureum, Fusarium tricinctum, Fusarium wilt,

[0105] Botrytis, Botrytis allii, Botrytis anthophila, Botrytis cinerea, Botrytis fabae, Botrytis narcissicola,

[0106] Alternaria, Alternaria alternata, Alternaria brassicae, Alternaria brassicicola, Alternaria carthami, Alternaria cinerariae, Alternaria dauci, Alternaria dianthi, Alternaria dianthicola, Alternaria euphorbiicola, Alternaria helianthi, Alternaria helianthicola, Alternaria japonica, Alternaria leucanthemi, Alternaria limicola, Alternaria linicola, Alternaria padwickii, Alternaria panax, Alternaria radicina, Alternaria raphani, Alternaria saponariae, Alternaria senecionis, Alternaria solani, Alternaria tenuissima, Alternaria triticina, Alternaria zinniae,

[0107] Erisyphe, Erisyphe necator, Erysiphe betae, Erysiphe brunneopunctata, Erysiphe cichoracearum, Erysiphe cruciferarum, Erysiphe graminis f. sp. Avenae, Erysiphe graminis f. sp. tritici, Erysiphe heraclei, Erysiphe pisi,

[0108] Claviceps, Claviceps fusiformis, Claviceps purpurea, Claviceps sorghi, Claviceps zizaniae,

[0109] Gaeumannomyces, Gaeumannomyces graminis,

[0110] Leptosphaeria, Leptosphaeria nodorum, Leptosphaeria acuta, Leptosphaeria cannabina, Leptosphaeria coniothyrium, Leptosphaeria libanotis, Leptosphaeria lindquistii, Leptosphaeria maculans, Leptosphaeria musarum, Leptosphaeria pratensis, Leptosphaeria sacchari, Leptosphaeria woroninii,

[0111] Microdochium, Microdochium spp. Microdochium bolleyi, Microdochium dimerum, Microdochium panattonianum, Microdochium phragmitis,

[0112] Mycosphaerella, Mycosphaerella arachidis, Mycosphaerella areola, Mycosphaerella berkeleyi, Mycosphaerella bolleana, Mycosphaerella brassicicola, Mycosphaerella caricae, Mycosphaerella caryigena, Mycosphaerella cerasella, Mycosphaerella coffeicola, Mycosphaerella confusa, Mycosphaerella cruenta, Mycosphaerella dendroides, Mycosphaerella eumusae, Mycosphaerella gossypina, Mycosphaerella graminicola, Mycosphaerella henningsii, Mycosphaerella horii, Mycosphaerella juglandis, Mycosphaerella lageniformis, Mycosphaerella linicola, Mycosphaerella louisianae, Mycosphaerella musae, Mycosphaerella musicola, Mycosphaerella palmicola, Mycosphaerella pinodes, Mycosphaerella pistaciarum, Mycosphaerella pistacina, Mycosphaerella platanifolia, Mycosphaerella polymorpha, Mycosphaerella pomi, Mycosphaerella punctiformis, Mycosphaerella pyri,

[0113] Oculimacula, Oculimacula acuformis, Oculimacula yallundae,

[0114] Blumeria, Blumeria graminis,

[0115] Pyrenophora, Pyrenophora avenae, Pyrenophora chaetomioides, Pyrenophora graminea, Pyrenophora seminiperda, Pyrenophora teres, Pyrenophora teres f. maculata, Pyrenophora teres f. teres, Pyrenophora tritici-repentis,

[0116] Ramularia, Ramularia collo-cygni, Ramularia beticola, Ramularia coryli, Ramularia cyclaminicola, Ramularia macrospora, Ramularia menthicola, Ramularia necator, Ramularia primulae, Ramularia spinaciae, Ramularia subtilis, Ramularia tenella, Ramularia vallisumbrosae,

[0117] Rhynchosporium, Rhynchosporium secalis,

[0118] Cochliobolus, Cochliobolus, Cochliobolus carbonum, Cochliobolus cymbopogonis, Cochliobolus hawaiiensis, Cochliobolus heterostrophus, Cochliobolus lunatus, Cochliobolus miyabeanus, Cochliobolus ravenelii, Cochliobolus sativus, Cochliobolus setariae, Cochliobolus spicifer, Cochliobolus stenospilus, Cochliobolus tuberculatus, Cochliobolus victoriae,

[0119] Microdochium, Microdochium oryzae,

[0120] Pyricularia, Pyricularia oryzae,

[0121] Sarocladiunn, Sarocladium oryzae,

[0122] Ustilaginoides, Ustilaginoides virens,

[0123] Cercospora, Cercospora, Cercospora apii, Cercospora apii f. sp. clerodendri, Cercospora apiicola, Cercospora arachidicola, Cercospora asparagi, Cercospora atrofiliformis, Cercospora beticola, Cercospora brachypus, Cercospora brassicicola, Cercospora brunkii, Cercospora cannabis, Cercospora cantuariensis, Cercospora capsici, Cercospora carotae, Cercospora corylina, Cercospora fuchsiae, Cercospora furca, Cercospora fusimaculans, Cercospora gerberae, Cercospora halstedii, Cercospora handelii, Cercospora hayi, Cercospora hydrangeae, Cercospora kikuchii, Cercospora lentis, Cercospora liquidambaris, Cercospora longipes, Cercospora longissima, Cercospora mamaonis, Cercospora mangiferae, Cercospora medicaginis, Cercospora melongenae, Cercospora minuta, Cercospora nicotianae, Cercospora odontoglossi, Cercospora papayae, Cercospora penniseti, Cercospora pisa-sativae, Cercospora platanicola, Cercospora puderii, Cercospora pulcherrima, Cercospora rhapidicola, Cercospora rosicola, Cercospora sojina, Cercospora solani, Cercospora solani-tuberosi, Cercospora sorghi, Cercospora theae, Cercospora tuberculans, Cercospora vexans, Cercospora vicosae, Cercospora zeae-maydis, Cercospora zebrina, Cercospora zonata, Corynespora, Corynespora cassiicola,

[0124] Phakospora, Phakospora pachyrhizi, Phakopsora gossypii, Colletotrichum, Colletotrichum acutatum, Colletotrichum arachidis, Colletotrichum capsici, Colletotrichum cereale, Colletotrichum coffeanum, Colletotrichum crassipes, Colletotrichum dematium, Colletotrichum dematium f. spinaciae, Colletotrichum derridis, Colletotrichum destructivum, Colletotrichum gloeosporioides, Colletotrichum glycines, Colletotrichum gossypii, Colletotrichum graminicola, Colletotrichum higginsianum, Colletotrichum kahawae, Colletotrichum lindemuthianum, Colletotrichum lini, Colletotrichum mangenotii, Colletotrichum musae, Colletotrichum nigrum, Colletotrichum orbiculare, Colletotrichum pili, Colletotrichum sublineolum, Colletotrichum trichellum, Colletotrichum trifolii, Colletotrichum truncatum,

[0125] Pythium spp,

[0126] Diplodia, Diplodia allocellula, Diplodia laelio-cattleyae, Diplodia manihoti, Diplodia paraphysaria, Diplodia seriata, Diplodia theae-sinensis,

[0127] Monilia, Monilinia azaleae, Monilinia fructicola, Monilinia fructigena, Monilinia laxa, Monilinia oxycocci,

[0128] Pezzicula, Pezzicula alba, Pezzicula malicorticis,

[0129] Zymoseptoria, Zymoseptoria tritici

[0130] Phytophthora, Phytophthora infestans

[0131] Guignardia, Guignardia bidwelli, Guignardia camelliae, Guignardia fulvida, Guignardia mangiferae, Guignardia musae, Guignardia philoprina,

[0132] Plasmopara, Plasmopara viticola,

[0133] Puccinia, Puccinia angustata, Puccinia arachidis, Puccinia aristidae, Puccinia asparagi, Puccinia cacabata, Puccinia campanulae, Puccinia carthami, Puccinia coronata, Puccinia dioicae, Puccinia erianthi, Puccinia extensicola, Puccinia helianthi, Puccinia hordei, Puccinia jaceae, Puccinia kuehnii, Puccinia malvacearum, Puccinia mariae-wilsoniae, Puccinia melanocephala, Puccinia menthae, Puccinia oxalidis, Puccinia pelargonii-zonalis, Puccinia pittieriana, Puccinia poarum, Puccinia purpurea, Puccinia recondita, Puccinia schedonnardii, Puccinia sessilis, Puccinia striiformis, Puccinia striiformis, Puccinia subnitens, Puccinia substriata, Puccinia verruca, Puccinia xanthii,

[0134] Rhizoctonia, Rhizoctonia solani, Rhizoctonia oryzae, Rhizoctonia cerealis, Rhizoctonia leguminicola, Rhizoctonia rubi,

[0135] Sclerotinia, Sclerotinia borealis, Sclerotinia bulborum, Sclerotinia minor, Sclerotinia ricini, Sclerotinia sclerotiorum, Sclerotinia spermophila, Sclerotinia trifoliorum,

[0136] Septoria, Septoria ampelina, Septoria azaleae, Septoria bataticola, Septoria campanulae, Septoria cannabis, Septoria cucurbitacearum, Septoria darrowii, Septoria dianthi, Septoria eumusae, Septoria glycines, Septoria helianthi, Septoria humuli, Septoria hydrangeae, Septoria lactucae, Septoria lycopersici, Septoria lycopersici, Septoria menthae, Septoria passerinii, Septoria pili, Septoria rhododendri, Septoria secalis, Septoria selenophomoides,

[0137] Venturia, Venturia inaequalis. Venturia carpophila,

[0138] Acrodontium, Acrodontium simplex,

[0139] Acrophialophora, Acrophialophora fusispora,

[0140] Acrosporium, Acrosporium tingitaninum,

[0141] Aecidiurn, Aecidium aechmantherae, Aecidium amaryllidis, Aecidium breyniae,

[0142] Aecidium campanulastri, Aecidium cannabis, Aecidium cantensis, Aecidium caspicum, Aecidium foeniculi, Aecidium narcissi,

[0143] Ahmadiago,

[0144] Albonectria, Albonectria rigidiuscula,

[0145] Allodus, Allodus podophylli,

[0146] Amphobotrys, Amphobotrys ricini,

[0147] Anguillosporella, Anguillosporella vermiformis,

[0148] Anthostomella, Anthostomella pullulans,

[0149] Antrodia, Antrodia albida, Antrodia serialiformis, Antrodia serialis,

[0150] Apiospora, Apiospora montagnei,

[0151] Appendiculella,

[0152] Armillaria Armillaria heimii, Armillaria sinapina, Armillaria socialis, Armillaria tabescens,

[0153] Arthrocladiella,

[0154] Arthuriomyces, Arthuriomyces peckianus,

[0155] Ascochyta, Ascochyta asparagina, Ascochyta bohemica, Ascochyta caricae, Ascochyta doronici, Ascochyta fabae f. sp. lentis, Ascochyta graminea, Ascochyta hordei, Ascochyta humuli, Ascochyta pili, Ascochyta prasadii, Ascochyta sorghi, Ascochyta spinaciae, Ascochyta tarda, Ascochyta tritici,

[0156] Ascospora, Ascospora ruborum,

[0157] Aspergillus, Aspergillus aculeatus, Aspergillus fischerianus, Aspergillus niger,

[0158] Asperisporium, Asperisporium caricae,

[0159] Asteridiella,

[0160] Asteroma, Asteroma caryae,

[0161] Athelia, Athelia arachnoidea, Athelia rolfsii,

[0162] Aurantiporus, Aurantiporus fissilis,

[0163] Aureobasidium, Aureobasidium pullulans,

[0164] Bambusiomyces,

[0165] Banana freckle,

[0166] Bayoud disease,

[0167] Beniowskia, Beniowskia sphaeroidea,

[0168] Bionectria, Bionectria ochroleuca,

[0169] Bipolaris, Bipolaris cactivora, Bipolaris cookei, Bipolaris incurvata, Bipolaris sacchari,

[0170] Biscogniauxia, Biscogniauxia capnodes, Biscogniauxia marginata,

[0171] Bjerkandera, Bjerkandera adusta,

[0172] Black sigatoka,

[0173] Blakeslea, Blakeslea trispora,

[0174] Botryodiplodia, Botryodiplodia oncidii, Botryodiplodia ulmicola,

[0175] Botryosphaeria, Botryosphaeria cocogena, Botryosphaeria dothidea, Botryosphaeria marconii, Botryosphaeria obtusa, Botryosphaeria rhodina, Botryosphaeria ribis, Botryosphaeria stevensii,

[0176] Botryosporium, Botryosporium pulchrum,

[0177] Botryotinia, Botryotinia fuckeliana, Botryotinia polyblastis,

[0178] Boxwood blight,

[0179] Brachybasidiaceae,

[0180] Brasiliomyces, Brasiliomyces malachrae,

[0181] Briosia, Briosia ampelophaga,

[0182] Brown ring patch,

[0183] Buckeye rot of tomato,

[0184] Bulbomicrosphaera,

[0185] Cadophora, Cadophora malorum,

[0186] Caespitotheca,

[0187] Calonectria, Calonectria ilicicola, Calonectria indusiata, Calonectria kyotensis, Calonectria pyrochroa, Calonectria quinqueseptata,

[0188] Camarotella, Camarotella acrocomiae, Camarotella costaricensis,

[0189] Canna rust,

[0190] Capitorostrum, Capitorostrum cocoes,

[0191] Capnodium, Capnodium footii, Capnodium mangiferum, Capnodium ramosum, Capnodium theae,

[0192] Cephalosporium, Cephalosporium gramineum,

[0193] Ceratobasidium, Ceratobasidium cereale, Ceratobasidium cornigerum, Ceratobasidium noxium, Ceratobasidium ramicola, Ceratobasidium setariae, Ceratobasidium stevensii,

[0194] Ceratocystis, Ceratocystis adiposa, Ceratocystis coerulescens, Ceratocystis fimbriata, Ceratocystis moniliformis, Ceratocystis oblonga, Ceratocystis obpyriformis, Ceratocystis paradoxa, Ceratocystis pilifera, Ceratocystis pluriannulata, Ceratocystis polyconidia, Ceratocystis tanganyicensis, Ceratocystis zombamontana,

[0195] Ceratorhiza, Ceratorhiza hydrophila,

[0196] Ceratospermopsis,

[0197] Cercoseptoria, Cercoseptoria ocellata,

[0198] Cercosporella, Cercosporella rubi,

[0199] Ceriporia, Ceriporia spissa, Ceriporia xylostromatoides,

[0200] Cerrena, Cerrena unicolor,

[0201] Ceuthospora, Ceuthospora lauri,

[0202] Choanephora, Choanephora cucurbitarum, Choanephora infundibulifera,

[0203] Chrysanthemum, Chrysanthemum white rust,

[0204] Chrysomyxa, Chrysomyxa cassandrae,

[0205] Chrysomyxa, Chrysomyxa himalensis, Chrysomyxa ledi, Chrysomyxa ledi var. rhododendri, Chrysomyxa ledicola, Chrysomyxa nagodhii, Chrysomyxa neoglandulosi, Chrysomyxa piperiana, Chrysomyxa pirolata, Chrysomyxa pyrolae, Chrysomyxa reticulata, Chrysomyxa roanensis, Chrysomyxa succinea,

[0206] Cladosporium, Cladosporium arthropodii, Cladosporium cladosporioides, Cladosporium cladosporioides f. sp. pisicola, Cladosporium cucumerinum, Cladosporium herbarum, Cladosporium musae, Cladosporium oncobae,

[0207] Climacodon, Climacodon pulcherrimus, Climacodon septentrionalis,

[0208] Clitocybe, Clitocybe parasitica,

[0209] Clonostachys rosea f. rosea,

[0210] Clypeoporthe, Clypeoporthe iliau,

[0211] Coleosporium, Coleosporium helianthi, Coleosporium ipomoeae, Coleosporium madiae, Coleosporium pacificum, Coleosporium tussilaginis,

[0212] Conidiosporomyces,

[0213] Coniella, Coniella castaneicola, Coniella diplodiella, Coniella fragariae,

[0214] Coniothecium, Coniothecium chomatosporum,

[0215] Coniothyrium, Coniothyrium celtidis-australis, Coniothyrium henriquesii, Coniothyrium rosarum, Coniothyrium wernsdorffiae,

[0216] Coprinopsis, Coprinopsis psychromorbida,

[0217] Cordana, Cordana johnstonii, Cordana musae, Coriolopsis floccosa,

[0218] Corn grey leaf spot,

[0219] Corticium, Corticium invisum, Corticium penicillatum, Corticium theae,

[0220] Coryneopsis, Coryneopsis rubi,

[0221] Coryneum, Coryneum rhododendri,

[0222] Covered smut,

[0223] Crinipellis, Crinipellis sarmentosa,

[0224] Cronartium, Cronartium ribicola,

[0225] Cryphonectriaceae,

[0226] Cryptobasidiaceae,

[0227] Cryptocline, Cryptocline cyclaminis,

[0228] Cryptomeliola,

[0229] Cryptosporella, Cryptosporella umbrina,

[0230] Cryptosporiopsis, Cryptosporiopsis tarraconensis,

[0231] Cryptosporiunn, Cryptosporium minimum,

[0232] Curvularia, Curvularia lunata, Curvularia caricae-papayae, Curvularia penniseti, Curvularia senegalensis, Curvularia trifolii,

[0233] Cyclaneusma needle cast,

[0234] Cylindrocarpon, Cylindrocarpon ianthothele var. ianthothele, Cylindrocarpon magnusianum, Cylindrocarpon musae,

[0235] Cylindrocladiella, Cylindrocladiella camelliae, Cylindrocladiella parva,

[0236] Cylindrocladium, Cylindrocladium clavatum, Cylindrocladium lanceolatum, Cylindrocladium peruvianum, Cylindrocladium pteridis,

[0237] Cylindrosporium, Cylindrosporium cannabinum, Cylindrosporium juglandis, Cylindrosporium rubi,

[0238] Cymadothea, Cymadothea trifolii,

[0239] Cytospora, Cytospora palmarum, Cytospora personate, Cytospora sacchari, Cytospora sacculus, Cytospora terebinthi,

[0240] Cytosporina, Cytosporina ludibunda,

[0241] Dactuliophora, Dactuliophora elongata,

[0242] Davidiella, Davidiella dianthi, Davidiella tassiana,

[0243] Deightoniella, Deightoniella papuana, Deightoniella torulosa,

[0244] Dendrophora, Dendrophora marconii, Dendrophora erumpens,

[0245] Denticularia, Denticularia mangiferae,

[0246] Dermea pseudotsugae,

[0247] Diaporthaceae,

[0248] Diaporthe, Diaporthe arctii, Diaporthe dulcamarae, Diaporthe eres, Diaporthe helianthi, Diaporthe lagunensis, Diaporthe lokoyae, Diaporthe melonis, Diaporthe orthoceras, Diaporthe perniciosa, Diaporthe phaseolorum, Diaporthe phaseolorum var. caulivora, Diaporthe phaseolorum var. phaseolorum, Diaporthe phaseolorum var. soja, Diaporthe rudis, Diaporthe tanakae, Diaporthe toxica,

[0249] Dicarpella, Dicarpella dryina,

[0250] Didymella, Didymella applanata, Didymella bryoniae, Didymella fabae, Didymella lycopersici

[0251] Didymosphaeria, Didymosphaeria arachidicola, Didymosphaeria taiwanensis,

[0252] Dilophospora, Dilophospora alopecuri,

[0253] Dimeriella, Dimeriella sacchari,

[0254] Diplocarpon, Diplocarpon mespili, Diplocarpon rosae,

[0255] Discosia, Discosia artocreas,

[0256] Discostroma, Discostroma corticola,

[0257] Distocercospora, Distocercospora livistonae,

[0258] Dothiorella, Dothiorella brevicollis, Dothiorella dominicana, Dothiorella dulcispinae, Dothiorella gregaria,

[0259] Drechslera, Drechslera avenacea, Drechslera campanulata, Drechslera dematioidea, Drechslera gigantea, Drechslera glycines, Drechslera musae-sapientium, Drechslera teres f. maculata, Drechslera wirreganensis,

[0260] Eballistra, Eballistra lineata, Eballistra oryzae,

[0261] Eballistraceae,

[0262] Echinodontium, Echinodontium ryvardenii, Echinodontium tinctorium,

[0263] Ectendomeliola,

[0264] Elsinoë, Elsinoë ampelina, Elsinoë batatas, Elsinoë brasiliensis, Elsinoë leucospila, Elsinoë randii, Elsinoë rosarum, Elsinoë sacchari, Elsinoë theae, Elsinoë veneta,

[0265] Endomeliola,

[0266] Endothia, Endothia radicalis,

[0267] Endothiella, Endothiella gyrosa,

[0268] Entorrhizomycetes,

[0269] Entyloma, Entyloma ageratinae, Entyloma dahliae, Entyloma ellisii,

[0270] Epicoccum, Epicoccum nigrum,

[0271] Erennothecium, Eremothecium coryli, Eremothecium gossypii,

[0272] Erysiphales,

[0273] Exobasidiaceae, Exobasidium burtii, Exobasidium reticulatum, Exobasidium vaccinii var. japonicum, Exobasidium vaccinii-uliginosi, Exobasidium vexans, xxophiala alcalophila,

[0274] Exophiala, Exophiala angulospora, Exophiala attenuata, Exophiala calicioides, Exophiala castellanii, Exophiala dermatitidis, Exophiala dopicola, Exophiala exophialae, Exophiala heteromorpha, Exophiala hongkongensis, Exophiala jeanselmei, Exophiala lecanii-corni, Exophiala mansonii, Exophiala mesophila, Exophiala moniliae, Exophiala negronii, Exophiala phaeomuriformis, Exophiala pisciphila, Exophiala psychrophila, Exophiala salmonis, Exophiala spinifera,

[0275] Fomes, Fomes lamaensis,

[0276] Fomitopsis, Fomitopsis rosea,

[0277] Fusicladium Fusicladium pisicola,

[0278] Fusicoccum, Fusicoccum aesculi, Fusicoccum amygdali, Fusicoccum quercus,

[0279] Galactonnyces, Galactomyces candidum,

[0280] Ganoderma, Ganoderma brownii, Ganoderma lobatum, Ganoderma megaloma,

[0281] Ganoderma meredithiae, Ganoderma orbiforme, Ganoderma philippii, Ganoderma sessile, Ganoderma tornatum, Ganoderma zonatum,

[0282] Geastrumia, Geastrumia polystigmatis,

[0283] Georgefischeriaceae,

[0284] Georgefischeriales,

[0285] Geosmithia, Geosmithia pallida,

[0286] Geotrichum, Geotrichum candidum, Geotrichum klebahnii,

[0287] Gibberella, Gibberella acuminata, Gibberella avenacea, Gibberella baccata, Gibberella cyanogena, Gibberella fujikuroi, Gibberella intricans, Gibberella pulicaris, Gibberella stilboides, Gibberella tricincta, Gibberella xylarioides, Gibberella zeae,

[0288] Gibellina, Gibellina cerealis,

[0289] Gibertella, Gilbertella persicaria,

[0290] Gjaerumiaceae,

[0291] Gliocladiopsis, Gliocladiopsis tenuis,

[0292] Gliocladium, Gliocladium vermoeseni,

[0293] Gloeocercospora, Gloeocercospora sorghi,

[0294] Gloeocystidiellum, Gloeocystidiellum porosum,

[0295] Gloeophyllum, Gloeophyllum mexicanum, Gloeophyllum trabeum,

[0296] Gloeoporus, Gloeoporus dichrous,

[0297] Gloeosporium, Gloeosporium cattleyae, Gloeosporium theae-sinensis,

[0298] Glomerella, Glomerella cingulata, Glomerella graminicola, Glomerella tucumanensis,

[0299] Gnomonia, Gnomonia caryae, Gnomonia comari, Gnomonia dispora, Gnomonia iliau, Gnomonia rubi,

[0300] Golovinomyces, Golovinomyces cichoracearum,

[0301] Graphiola phoenicis,

[0302] Graphiolaceae,

[0303] Graphium, Graphium rigidum, Graphium rubrum,

[0304] Graphyllium, Graphyllium pentamerum,

[0305] Grovesinia, Grovesinia pyramidalis,

[0306] Gymnoconia, Gymnoconia nitens,

[0307] Gymnopus, Gymnopus dryophilus,

[0308] Gymnosporangium, Gymnosporangium kernianum, Gymnosporangium libocedri, Gymnosporangium nelsonii, Gymnosporangium yamadae,

[0309] Haematonectria, Haematonectria haematococca,

[0310] Hansenula, Hansenula subpelliculosa,

[0311] Hapalosphaeria, Hapalosphaeria deformans,

[0312] Haplobasidion, Haplobasidion musae,

[0313] Helicobasidium, Helicobasidium compactum, Helicobasidium longisporum, Helicobasidium purpureum,

[0314] Helicoma, Helicoma muelleri,

[0315] Helminthosporium, Helminthosporium cookei, Helminthosporium solani,

[0316] Hendersonia, Hendersonia creberrima, Hendersonia theicola,

[0317] Hericium, Hericium coralloides,

[0318] Heterobasidion, Heterobasidion irregulare, Heterobasidion occidentale,

[0319] Hexagonia, Hexagonia hydnoides,

[0320] Hymenula, Hymenula affinis,

[0321] Hyphodermella, Hyphodermella corrugata,

[0322] Hyphodontia, Hyphodontia aspera, Hyphodontia sambuci,

[0323] Hypoxylon, Hypoxylon tinctor,

[0324] Inonotus, Inonotus arizonicus, Inonotus cuticularis, Inonotus dryophilus, Inonotus hispidus, Inonotus ludovicianus,

[0325] Irpex, Irpex destruens, Irpex lacteus,

[0326] Kabatiella, Kabatiella caulivora,

[0327] Karnal bunt,

[0328] Koa wilt,

[0329] Kretzschmaria, Kretzschmaria zonata,

[0330] Kuehneola, Kuehneola uredinis,

[0331] Kutilakesa, Kutilakesa pironii,

[0332] Laetiporus, Laetiporus ailaoshanensis, Laetiporus baudonii, Laetiporus caribensis, Laetiporus conifericola, Laetiporus cremeiporus, Laetiporus gilbertsonii, Laetiporus huroniensis, Laetiporus montanus, Laetiporus portentosus, Laetiporus zonatus,

[0333] Laxitextum, Laxitextum bicolor,

[0334] Leandria, Leandria momordicae,

[0335] Lentinus, Lentinus tigrinus,

[0336] Lenzites, Lenzites betulina, Lenzites elegans,

[0337] Leohumicola, Leohumicola atra, Leohumicola incrustata, Leohumicola levissima, Leptodontidium, Leptodontidium elatius,

[0338] Leptographium, Leptographium microsporum,

[0339] Leptosphaerulina, Leptosphaerulina crassiasca, Leptosphaerulina trifolii,

[0340] Leptothyrium, Leptothyrium nervisedum,

[0341] Leptotrochila, Leptotrochila medicaginis,

[0342] Leucocytospora, Leucocytospora leucostoma,

[0343] Leucostoma, Leucostoma auerswaldii, Leucostoma canker, Leucostoma kunzei,

[0344] Leucostoma persoonii,

[0345] Leveillula, Leveillula cornpositarum, Leveillula leguminosarum, Leveillula taurica,

[0346] Limacinula, Limacinula tenuis,

[0347] Linochora, Linochora graminis,

[0348] Loose smut,

[0349] Lopharia, Lopharia crassa,

[0350] Lophodermium, Lophodermium aucupariae, Lophodermium schweinitzii,

[0351] Macrophoma, Macrophoma mangiferae, Macrophoma theicola,

[0352] Macrosporium, Macrosporium cocos,

[0353] Magnaporthe, Magnaporthe grisea, Magnaporthe salvinii,

[0354] Magnaporthiopsis,

[0355] Mamianiella, Mamianiella coryli,

[0356] Marasmiellus, Marasmiellus cocophilus, Marasmiellus stenophyllus,

[0357] Marasmius, Marasmius crinis-equi, Marasmius sacchari, Marasmius semiustus, Marasmius stenophyllus, Marasmius tenuissimus,

[0358] Massarina, Massarina walkeri,

[0359] Mauginiella, Mauginiella scaettae,

[0360] Melampsora, Melampsora lini, Melampsora occidentalis,

[0361] Melanconis, Melanconis carthusiana,

[0362] Melanconium, Melanconium juglandinum,

[0363] Meliola, Meliola mangiferae, Meliola zangii,

[0364] Meruliopsis, Meruliopsis ambigua,

[0365] Microascus, Microascus brevicaulis,

[0366] Microbotryum, Microbotryum silenes-dioicae, Microbotryum violaceum,

[0367] Microsphaera, Microsphaera coryli, Microsphaera diffusa, Microsphaera ellisii,

[0368] Microsphaera euphorbiae, Microsphaera hommae, Microsphaera penicillata, Microsphaera vaccinii, Microsphaera verruculosa,

[0369] Microstroma, Microstroma juglandis,

[0370] Moesziomyces, Moesziomyces bullatus,

[0371] Moniliophthora, Moniliophthora roreri,

[0372] Monilochaetes, Monilochaetes infuscans,

[0373] Monochaetia, Monochaetia coryli, Monochaetia mali,

[0374] Monographella, Monographella albescens, Monographella cucumerina, Monographella nivalis,

[0375] Monosporascus, Monosporascus cannonballus, Monosporascus eutypoides,

[0376] Monostichella, Monostichella coryli,

[0377] Mucor, Mucor circinelloides, Mucor hiemalis, Mucor mucedo, Mucor paronychius,

[0378] Mucor piriformis, Mucor racemosus,

[0379] Mycena, Mycena citricolor,

[0380] Mycocentrospora, Mycocentrospora acerina,

[0381] Mycoleptodiscus, Mycoleptodiscus terrestris,

[0382] Didymella, Didymella rabiei,

[0383] Mycosphaerella, Mycosphaerella recutita, Mycosphaerella rosicola, Mycosphaerella rubi, Mycosphaerella stigmina-platani, Mycosphaerella striatiformans,

[0384] Mycovellosiella, Mycovellosiella concors,

[0385] Passalora, Passalora fulva,

[0386] Mycovellosiella, Mycovellosiella koepkei, Mycovellosiella vaginae,

[0387] Myriogenospora, Myriogenospora aciculispora,

[0388] Myrothecium, Myrothecium roridum, Myrothecium verrucaria,

[0389] Naevala, Naevala perexigua,

[0390] Naohidemyces, Naohidemyces vaccinii,

[0391] Nectria, Nectria cinnabarina, Nectria ditissima, Nectria foliicola, Nectria mammoidea, Nectria mauritiicola, Nectria peziza, Nectria pseudotrichia, Nectria radicicola, Nectria ramulariae,

[0392] Nectriella, Nectriella pironii,

[0393] Nemania, Nemania diffusa, Nemania serpens,

[0394] Neocosmospora, Neocosmospora vasinfecta,

[0395] Neodeightonia, Neodeightonia phoenicum,

[0396] Neoerysiphe, Neoerysiphe galeopsidis,

[0397] Neofabraea, Neofabraea perennans,

[0398] Neofusicoccum, Neofusicoccum mangiferae,

[0399] Oidiopsis, Oidiopsis gossypii,

[0400] Oidium, Oidium arachidis, Oidium caricae-papayae, Oidium indicum, Oidium mangiferae, Oidium manihotis,

[0401] Olpidium, Olpidium brassicae,

[0402] Omphalia, Omphalia tralucida,

[0403] Ophiobolus, Ophiobolus anguillides, Ophiobolus cannabinus,

[0404] Ophioirenina,

[0405] Ovulinia, Ovulinia azaleae,

[0406] Oxyporus, Oxyporus corticola,

[0407] Ozonium, Ozonium texanum,

[0408] Peltaster, Peltaster fructicola,

[0409] Penicillium, Penicillium expansum, Penicillium funiculosum,

[0410] Peniophora,

[0411] Periconia, Periconia circinata,

[0412] Periconiella, Periconiella cocoes,

[0413] Peridernniurn, Peridermium califomicum,

[0414] Pestalosphaeria, Pestalosphaeria concentrica,

[0415] Pestalotia, Pestalotia longiseta, Pestalotia rhododendri,

[0416] Pestalotiopsis, Pestalotiopsis adusta, Pestalotiopsis arachidis, Pestalotiopsis disseminata, Pestalotiopsis guepini, Pestalotiopsis leprogena, Pestalotiopsis longiseta, Pestalotiopsis mangiferae, Pestalotiopsis palmarum, Pestalotiopsis sydowiana, Pestalotiopsis theae,

[0417] Peyronellaea, Peyronellaea curtisii,

[0418] Phacidiopycnis, Phacidiopycnis padwickii,

[0419] Phaeochoropsis, Phaeochoropsis mucosa,

[0420] Phaeocytostronna, Phaeocytostroma iliau, Phaeocytostroma sacchari,

[0421] Phaeoisariopsis, Phaeoisariopsis bataticola,

[0422] Phaeoramularia, Phaeoramularia heterospora, Phaeoramularia indica, Phaeoramularia manihotis,

[0423] Phaeoseptoria, Phaeoseptoria musae,

[0424] Phaeosphaerella, Phaeosphaerella mangiferae, Phaeosphaerella theae, Phaeosphaeria, Phaeosphaeria avenaria, Phaeosphaeria herpotrichoides, Phaeosphaeria microscopica, Phaeosphaeria nodorum,

[0425] Phaeosphaeriopsis, Phaeosphaeriopsis obtusispora,

[0426] Phaeotrichoconis, Phaeotrichoconis crotalariae,

[0427] Phialophora, Phialophora asteris, Phialophora cinerescens, Phialophora gregata, Phialophora tracheiphila,

[0428] Phoma, Phoma clematidina, Phoma costaricensis, Phoma cucurbitacearum, Phoma destructiva, Phoma draconis, Phoma exigua, Phoma exigua, Phoma exigua var. foveata, Phoma exigua, Phoma glomerata, Phoma glycinicola, Phoma herbarum, Phoma insidiosa, Phoma medicaginis, Phoma microspora, Phoma narcissi, Phoma nebulosa, Phoma oncidii-sphacelati, Phoma pinodella, Phoma sclerotioides, Phoma strasseri,

[0429] Phomopsis, Phomopsis asparagi, Phomopsis asparagicola, Phomopsis cannabina, Phomopsis coffeae, Phomopsis ganjae, Phomopsis javanica, Phomopsis longicolla, Phomopsis mangiferae, Phomopsis prunorum, Phomopsis sclerotioides, Phomopsis theae,

[0430] Phragmidium, Phragmidium mucronatum, Phragmidium rosae-pimpinellifoliae, Phragmidium rubi-idaei, Phragmidium violaceum,

[0431] Phyllachora, Phyllachora banksiae, Phyllachora cannabis, Phyllachora graminis, Phyllachora gratissima, Phyllachora musicola, Phyllachora pomigena, Phyllachora sacchari,

[0432] Phyllactinia,

[0433] Phyllosticta, Phyllosticta alliariaefoliae Phyllosticta arachidis-hypogaeae, Phyllosticta batatas, Phyllosticta capitalensis, Phyllosticta carpogena, Phyllosticta coffeicola, Phyllosticta concentrica, Phyllosticta coryli, Phyllosticta cucurbitacearum, Phyllosticta cyclaminella, Phyllosticta erratica, Phyllosticta hawaiiensis, Phyllosticta lentisci, Phyllosticta manihotis, Phyllosticta micropuncta, Phyllosticta mortonii, Phyllosticta nicotianae, Phyllosticta palmetto, Phyllosticta penicillariae, Phyllosticta perseae, Phyllosticta pseudocapsici, Phyllosticta sojaecola, Phyllosticta theae, Phyllosticta theicola,

[0434] Phymatotrichopsis, Phymatotrichopsis omnivora,

[0435] Physalospora, Physalospora disrupta, Physalospora perseae,

[0436] Physoderma, Physoderma alfalfae, Physoderma leproides, Physoderma trifolii,

[0437] Physopella, Physopella ampelopsidis,

[0438] Pileolaria, Pileolaria terebinthi,

[0439] Piricaudiopsis, Piricaudiopsis punicae, Piricaudiopsis rhaphidophorae, Piricaudiopsis rosae,

[0440] Plenodomus, Plenodomus destruens, Plenodomus meliloti,

[0441] Pleosphaerulina, Pleosphaerulina sojicola,

[0442] Pleospora, Pleospora alfalfae, Pleospora betae, Pleospora herbarum, Pleospora lycopersici, Pleospora tarda, Pleospora theae,

[0443] Pleuroceras,

[0444] Podosphaera, Podosphaera fuliginea, Podosphaera furca, Podosphaera leucotricha, Podosphaera macularis, Podosphaera pannosa,

[0445] Polyscytalum, Polyscytalum pustulans,

[0446] Poria, Poria hypobrunnea,

[0447] Postia, Postia tephroleuca,

[0448] Powdery mildew,

[0449] Pseudocercospora, Pseudocercospora arecacearum, Pseudocercospora cannabina, Pseudocercospora fuligena, Pseudocercosporella herpotrichoides, Pseudocercospora gunnerae, Pseudocercospora pandoreae, Pseudocercospora puderi, Pseudocercospora rhapisicola, Pseudocercospora theae, Pseudocercospora vitis, Pseudocercosporella capsellae,

[0450] Pseudocochliobolus, Pseudocochliobolus eragrostidis,

[0451] Pseudoepicoccum, Pseudoepicoccum cocos,

[0452] Pseudopeziza, Pseudopeziza jonesii, Pseudopeziza medicaginis, Pseudopeziza trifolii,

[0453] Pseudoseptoria, Pseudoseptoria donacis,

[0454] Pucciniaceae,

[0455] Pucciniastrum, Pucciniastrum americanurn, Pucciniastrum arcticum, Pucciniastrum epilobii, Pucciniastrum hydrangeae,

[0456] Pycnostysanus, Pycnostysanus azaleae,

[0457] Pyrenochaeta, Pyrenochaeta lycopersici, Pyrenochaeta terrestris,

[0458] Pyrenopeziza, Pyrenopeziza brassicae,

[0459] Rannichloridiunn, Ramichloridium musae,

[0460] Ramulispora, Ramulispora sorghi, Ramulispora sorghicola,

[0461] Rhinocladium, Rhinocladium corticola,

[0462] Rhizophydium, Rhizophydium graminis,

[0463] Rhizopus, Rhizopus arrhizus, Rhizopus circinans, Rhizopus microsporus, Rhizopus oryzae,

[0464] Rhytisma, Rhytisma punctatum, Rhytisma vitis,

[0465] Rigidoporus, Rigidoporus vinctus,

[0466] Rosellinia, Rosellinia arcuata, Rosellinia bunodes, Rosellinia necatrix, Rosellinia pepo,

[0467] Saccharicola, Saccharicola taiwanensis,

[0468] Schiffnerula, Schiffnerula cannabis,

[0469] Schizophyllum, Schizophyllum commune,

[0470] Schizopora, Schizopora flavipora,

[0471] Schizothyrium, Schizothyrium pomi,

[0472] Sclerophthora, Sclerophthora macrospora,

[0473] Sclerotium, Sclerotium cinnamomi, Sclerotium delphinii,

[0474] Scytinostroma, Scytinostroma galactinum,

[0475] Seimatosporium, Seimatosporium mariae, Seimatosporium rhododendri,

[0476] Selenophoma, Selenophoma linicola,

[0477] Septobasidium, Septobasidium bogoriense, Septobasidium euryae-groffii, Septobasidium gaoligongense, Septobasidium pilosum, Septobasidium polygoni, Septobasidium pseudopedicellatum, Septobasidium theae,

[0478] Septocyta, Septocyta ruborum,

[0479] Serpula, Serpula lacrymans,

[0480] Setosphaeria, Setosphaeria rostrata, Setosphaeria turcica,

[0481] Spencermartinsia, Spencermartinsia pretoriensis,

[0482] Sphaceloma, Sphaceloma arachidis, Sphaceloma menthae, Sphaceloma perseae, Sphaceloma poinsettiae, Sphaceloma sacchari, Sphaceloma theae,

[0483] Sphacelotheca, Sphacelotheca reiliana, Sphaerotheca castagnei,

[0484] Sphaerulina, Sphaerulina oryzina, Sphaerulina rehmiana, Sphaerulina rubi,

[0485] Sphenospora, Sphenospora kevorkianii,

[0486] Spilocaea, Spilocaea oleaginea,

[0487] Sporisoriurn, Sporisorium cruenturn, Sporisorium ehrenbergii, Sporisorium scitamineurn, Sporisorium sorghi,

[0488] Sporonenna, Sporonema phacidioides,

[0489] Stagonospora, Stagonospora avenae, Stagonospora meliloti, Stagonospora recedens, Stagonospora sacchari, Stagonospora tainanensis,

[0490] Stagonosporopsis,

[0491] Stegocintractia, Stegocintractia junci,

[0492] Stemphylium, Stemphylium alfalfae, Stemphylium bolickii, Stemphylium cannabinum, Stemphylium globuhferum, Stemphylium lycopersici, Stemphylium sarciniforme, Stemphylium solani, Stemphylium vesicarium,

[0493] Stenella, Stenella anthuriicola,

[0494] Stigmatomycosis,

[0495] Stigmina, Stigmina carpophila, Stigmina palmivora, Stigmina platani-racemosae,

[0496] Stronnatinia, Stromatinia cepivora,

[0497] Sydowiella, Sydowiella depressula,

[0498] Sydowiellaceae,

[0499] Synchytriurn, Synchytrium endobioticum,

[0500] Tapesia, Tapesia acuformis, Tapesia yallundae,

[0501] Taphrina, Taphrina coryli, Taphrina potentillae,

[0502] Thanatephorus, Thanatephorus cucumeris,

[0503] Thecaphora, Thecaphora solani,

[0504] Thielaviopsis, Thielaviopsis basicola, Thielaviopsis ceramica,

[0505] Thyrostroma, Thyrostroma cornpactum,

[0506] Tiarosporella, Tiarosporella urbis-rosarum,

[0507] Tilletia, Tilletia barclayana, Tilletia caries, Tilletia controversa, Tilletia laevis, Tilletia tritici, Tilletia walkeri,

[0508] Tilletiariaceae,

[0509] Togniniaceae,

[0510] Tranzschelia, Tranzschelia pruni-spinosae,

[0511] Trichoderma, Trichoderma koningii, Trichoderma paucisporum, Trichoderma songyi, Trichoderma theobromicola, Trichoderma viride,

[0512] Tubercularia, Tubercularia lateritia,

[0513] Tunstallia, Tunstallia aculeata,

[0514] Typhula, Typhula blight, Typhula idahoensis, Typhula incarnata, Typhula ishikariensis, Typhula variabilis,

[0515] Ulocladium, Ulocladium consortiale,

[0516] Uncinula,

[0517] Uredo, Uredo behnickiana, Uredo kriegeriana, Uredo musae, Uredo nigropuncta, Uredo rangelii,

[0518] Urocystis, Urocystis agropyri, Urocystis brassicae, Urocystis occulta, Uromyces, Uromyces apiosporus, Uromyces appendiculatus, Uromyces beticola, Uromyces ciceris-arietini, Uromyces dianthi, Uromyces euphorbiae, Uromyces graminis, Uromyces inconspicuus, Uromyces lineolatus, Uromyces musae, Uromyces oblongus, Uromyces pisi-sativi, Uromyces proëminens, Uromyces medicaginis, Uromyces trifolii-repentis, Uromyces viciae-fabae,

[0519] Urophlyctis, Urophlyctis leproides, Urophlyctis trifolii,

[0520] Ustilaginales,

[0521] Ustilago, Ustilago avenae, Ustilago esculenta, Ustilago hordei, Ustilago maydis, Ustilago nigra, Ustilago nuda, Ustilago scitaminea, Ustilago tritici,

[0522] Vankya, Vankya ornithogali,

[0523] Velvet blight,

[0524] Veronaea, Veronaea musae,

[0525] Verticillium, Verticillium albo-atrum, Verticillium alfalfae, Verticillium dahliae, Verticillium isaacii, Verticillium klebahnii, Verticillium longisporum, Verticillium nonalfalfae, Verticillium theobromae, Verticillium wilt, Verticillium zaregamsianum,

[0526] Waitea, Waitea circinata,

[0527] Westea,

[0528] Wheat leaf rust,

[0529] Wheat mildew,

[0530] Wuestneiopsis, Wuestneiopsis georgiana,

[0531] Xeromphalina, Xeromphalina fraxinophila,

[0532] Zopfia, Zopfia rhizophila,

[0533] Zygosaccharomyces, Zygosaccharomyces bailii, Zygosaccharomyces florentinus,

[0534] Zythiostroma.

[0535] Preferably, the pairs of fungi, oomycetes or bacteria vs. crop plants covered by the invention are the following:

[0536] Wheat (Triticum sativum)

[0537] Claviceps purpurea, Erysiphe graminis, Fusarium avenaceum, Fusarium culmorum, Fusarium graminearum, Fusarium langsethiae, Fusarium poae, Fusarium pseudograminearum, Gaeumannomyces graminis, Leptosphaeria nodorum, Microdochium spp., Mycosphaerella graminicola, Oculimacula acuformis, Oculimacula yallundae, Puccinia recôndita, Puccinia striiformis, Pyrenophora tritici-repentis, Rhizoctonia cerealis, Microdochium and Zymoseptoria tritici

[0538] Maize (Zea mays)

[0539] Fusarium graminearum, Fusarium proliferatum, Fusarium subglutinans, Fusarium verticillioides

[0540] Barley (Hordeum vulgare)

[0541] Blumeria graminis, Fusarium spp., Pyrenophora teres, Ramularia collo-cygni, Rhynchosporium secalis

[0542] Rice (Oryza sativa)

[0543] Cochliobolus miyabeanus, Fusarium fijikuroï, Magnaporthe oryzae, Microdochium oryzae, Pyricularia oryzae, Rhizoctonia oryzae, Rhizoctonia solani, Sarocladium oryzae, Ustilaginoides virens

[0544] Potato (Solanum tuberosum)

[0545] Alternia alternata, Alternaria solani, Phytophtora infestans, Rhizoctonia solani

[0546] Grapevine (Vinis vitifera)

[0547] Botrytis cinerea, Erysiphe necator, Plasmopara viticola, Guignardia bidwelli, Erisyphe necator, Diplodia seriata

[0548] Soya (Glycine max)

[0549] Cercopora kikuchii, Colletotrichum dematium, Corynespora cassficola, Fusarium graminearum, Pythium spp., Rhizoctonia solani, Sclerotinia sclerotiorum, Septoria glycines

[0550] Apple tree (Malus domestica)

[0551] Monilia fructigena, Monilia taxa, Pezzicula alba, Pezzicula malicorticis, Venturia inaequalis

[0552] Tomato (Lycopersicon esculentum)

[0553] Phytophtora infestans

[0554] Bean (Phaseolus vulgaris)

[0555] Uromyces appendiculatus

[0556] Radish (Raphanus sativus)

[0557] Alternaria brassicae

[0558] All fruits and vegetables

[0559] Botrytis cinerea

[0560] Strawberry plant (Fragaria sp.)

[0561] Colletotrichum acutatum

[0562] Carrot (Daucus carota)

[0563] Aternaria alternata, Alternaria dauci, Alternaria radicina

[0564] Peach (Prunus persica) and Apricot (Prunus armeniaca)

[0565] Monilia fructicola, Monilia fructigena, Monilia taxa

[0566] Particularly preferably, the pairs of fungi or bacteria vs. crop plants covered by the invention are the following:

[0567] Wheat: Fusarium graminearum, Microdochium and Zymoseptoria tritici

[0568] Grapevine: Botrytis cinerea, Erysiphe necator, Plasmopara viticola, Guignardia bidwelli, Erisyphe necator, Diplodia seriata

[0569] Potato: Alternia alternata, Alternaria solani, Phytophtora infestans, Rhizoctonia solani

[0570] Tomato: Phytophtora infestans

[0571] Control Process

[0572] The invention also relates to a process for controlling crop plant and seed pathogenic fungi, oomycetes and/or bacteria, comprising applying to crop plants the molecule of formula (I):

##STR00011##

[0573] wherein: [0574] R.sub.1 is selected from the group consisting of:

##STR00012##

[0575] where: [0576] R.sub.3 represents H or SO.sub.3Na, [0577] R.sub.4 is H or OH, [0578] represents a single or double bond, [0579] n is equal to 0 or 1 and [0580] m is 0 or 1; and [0581] R.sub.2 is selected from the group consisting of:

##STR00013##

[0582] Preferably, R1 is:

##STR00014##

[0583] wherein R.sub.3 is H or SO.sub.3Na.

[0584] Preferably, R2 is:

##STR00015##

[0585] This control can be curative or preventive, preferably curative.

[0586] Application to crop plants may be carried out by any means known to the skilled person for reaching the plant parts affected by the fungus and/or bacterium.

[0587] The molecule of formula (I) is applied at a dose between 0.1 and 5 mg/mL, preferably between 0.5 and 3 mg/mL, in a particularly preferred manner between 0.75 and 1 mg/mL.

[0588] Seed coating may be carried out by any technique known to the skilled person allowing the active agent to remain in contact with the seed.

[0589] For example, coating may be carried out by powdering or spraying.

[0590] For example, the coating may comprise formulants and additives.

[0591] Formulants are used to allow the active substance(s) to be applied to and remain on the seed in equal and constant proportion throughout the product application process at very low doses.

[0592] Formulants include: organic solvents or water, dispersants, emulsifiers, surfactants or wetting agents, dyes, etc.

[0593] Surfactants and emulsifiers have the property of combining and stably maintaining together two incompatible liquids.

[0594] Various adjuvants may be applied to the seed. Film coatings correspond to the application of a microporous film to the seed surface. They do not change the shape or size of the seed. They improve the coverage and homogeneity of the treatment. When the farmer uses the seeds, they are easier to handle during sowing by suppressing dust and facilitating seed flow into the seeder. They improve the action of the active substance(s) under cultivation conditions. Coatings change the shape, size and weight of the seed. They improve sowing accuracy.

[0595] The treatment processes for controlling crop plant and seed pathogenic fungi and/or bacteria according to the invention are particularly suitable against Fusarium disease, preferably a Fusarium disease listed in Table 1.

TABLE-US-00001 TABLE 1 Summary of Fusarium diseases Disease name Pathogen EPPO code Fusarium foot rot Fusarium culmorum FUSACU of asparagus Fusarium foot rot Fusarium solani FUSASH of bean f. sp. phaseoli Fusarium foot rot Fusarium solani FUSASI of pea f. sp. pisi Fusarium wilt of Fusarium oxysporum FUSABE sugarbeet f. sp. betae Fusarium wilt of Fusarium coeruleum FUSASC potato Fusarium wilt of Fusarium oxysporum FUSACO cabbage f. sp. conglutinans Fusarium stalk rot Gibberella fujikuroi GIBBFU of maize Fusarium stalk rot Fusarium culmorum FUSACU of maize Fusarium stalk rot Gibberella zeae GIBBZE of maize Fusarium wilt of Fusarium oxysporum FUSAVN vanilla f. sp. vanillae Fusarium wilt of Gibberella fujikuroi GIBBFS pineapple var. subglutinans Fusarium head blight Fusarium poae FUSAPO of maize Fusarium head blight Fusarium tricinctum FUSATI of maize Fusarium wilt of Fusarium oxysporum FUSADI carnation f. sp. dianthi Fusarium wilt of Fusarium oxysporum FUSAAE bromeliad f. sp. aechmeae Fusarium wilt of Fusarium oxysporum FUSAGL gladiolus f. sp. gladioli Fusarium head blight Fusarium culmorum FUSACU of cereals Fusarium head blight Gibberella rosea FUSARO of cereals Fusarium head blight Gibberella avenacea GIBBAV of cereals Fusarium head blight Gibberella intricans GIBBIN of cereals Fusarium head blight Monographella nivalis MONGNI of cereals Fusarium ear rot Gibberella zeae GIBBZE Fusarium root rot Fusarium oxysporum FUSAAS of asparagus f. sp. asparagi Fusarium root rot Fusarium oxysporum FUSAOP of cactus f. sp. opuntiarum Fusarium root and Fusarium oxysporum FUSARL crown rot of tomato f. sp. radicis-lycopersici Fusarium root and Fusarium oxysporum FUSACC crown rot of cucumber f. sp. cucumerinum Fusarium head Gibberella fujikuroi GIBBFU blight of wheat Fusarium wilt of Albonectria rigidiuscula CALORI cocoa Fusarium wilt of Gibberella stilboides GIBBST coffee Fusarium wilt of Fusarium oxysporum FUSACA safflower f. sp. carthami Fusarium wilt of Gibberella baccata GIBBBA quince Fusarium wilt of Fusarium solani FUSASU cucurbits f. sp. cucurbitae Fusarium wilt of Fusarium oxysporum FUSAVA cotton f. sp. vasinfectum Fusarium wilt of Fusarium oxysporum FUSAGE gerbera f. sp. gerberae Fusarium wilt of Fusarium oxysporum FUSAGL gladiolus f. sp. gladioli Fusarium wilt of Fusarium oxysporum FUSALI flax f. sp. lini Fusarium head blight Gibberella acuminata GIBBAC of maize Fusarium head blight Gibberella fujikuroi GIBBFS of maize var. subglutinans Fusarium head blight Gibberella zeae GIBBZE of maize Fusarium wilt of Fusarium oxysporum FUSAEL palm f. sp. elaeidis Fusarium wilt of Fusarium oxysporum FUSAGY soybean f. sp. glycines Fusarium wilt of Fusarium oxysporum FUSATR soybean f. sp. tracheiphilum Fusarium tuber rot Gibberella cyanogena GIBBCN of potato Fusarium root rot Gibberella fujikuroi GIBBFU of rice Fusarium snow mould Monographella nivalis MONGNI Fusarium dieback Gibberella rosea FUSARO Fusarium vascular Fusarium oxysporum FUSAOX wilt Fusarium vascular Fusarium oxysporum FUSALE wilt of lentil f. sp. lentis Fusarium vascular Fusarium oxysporum FUSANV wilt of watermelon f. sp. niveum Fusarium vascular Fusarium oxysporum FUSALY wilt of tomato f. sp. lycopersici Fusarium vascular Fusarium oxysporum FUSATU wilt of tulip f. sp. tulipae Fusarium vascular Fusarium oxysporum FUSACO wilt of crucifers f. sp. conglutinans Fusarium vascular Gibberella xylarioides GIBBXY wilt of coffee Fusarium vascular Fusarium oxysporum FUSACO wilt of cabbage f. sp. conglutinans Fusarium vascular Fusarium oxysporum FUSACH wilt of chrysanthemum f. sp. chrysanthemi Fusarium vascular Fusarium oxysporum FUSACCC wilt of cucumber f. sp. cucumerinum Fusarium vascular Fusarium oxysporum FUSAAU wilt of cyclamen var. aurantiacum Fusarium vascular Fusarium oxysporum FUSAFR wilt of strawberry f. sp. fragariae Fusarium vascular Fusarium oxysporum FUSAPH wilt of bean f. sp. phaseoli Fusarium vascular Fusarium oxysporum FUSAME wilt of melon f. sp. melonis Fusarium vascular Fusarium oxysporum FUSAPI wilt of pea f. sp. pisi Fusarium vascular Gibberella baccata GIBBBA wilt of chickpea Fusarium vascular Fusarium oxysporum FUSACI wilt of chickpea f. sp. ciceris Fusarium vascular Fusarium oxysporum FUSARA wilt of radish f. sp. raphani

[0596] The treatment processes for controlling crop plant and seed pathogenic fungi, oomycetes and/or bacteria according to the invention are particularly suitable for the following pairs of fungi or bacteria vs. crop plants:

[0597] Wheat: Fusarium graminearum, Microdochium nivale and Zymoseptoria tritici

[0598] Grapevine: Botrytis cinerea, Plasmopara viticola, Guignardia bidwelli, Erisyphe necator, Diplodia seriata

[0599] Apple tree: Venturia inaequalis

[0600] Banana tree: Fusarium oxysporum and Mycosphaerella fijiensis

EXAMPLES

[0601] Materials & Methods

Example 1: Microalgae Culture

[0602] The microalga Amphidinium carterae, strain AC208, comes from Algobank (Caen) and the microalgae Prymnesium parvum, strain RCC 1436, and Phaeodactylum tricornutum, strain CCMP 632, come from the Roscoff marine microorganism bank (RCC: Roscoff Culture Collection). These microalgae are cultivated in L1 artificial seawater (https://ncma.bigelow.org/algal-recipes) at 19° C. with a 12 h/12 h day/night cycle. The light intensity used is 100 μE. Biomass is recovered at the end of the exponential growth phase by centrifugation (15 min at 3000 RPM). The resulting cell pellet is frozen and then freeze-dried using a laboratory freeze-dryer (Alpha 1-2 LDplus, Labconco) for stable long-term preservation of the active substance. After freeze-drying, the dry matter is weighed.

Example 2: Preparation of the Extract

[0603] In order to extract the active substance from the dry matter of Example 1, 20 mg of dry matter is resuspended in 1 mL of distilled water at 100° C. After incubation for 2 minutes at room temperature (20-25° C.) the extract is stored in ice and then centrifuged for 5 min at 10 000 RPM at room temperature. The supernatant containing the active substance is frozen in liquid nitrogen for long-term preservation of its antifungal properties.

Example 3: Fusarium graminearum Germination Test

[0604] Fusarium graminearum spores are grown in “mung bean” depleted medium. Spores are separated from the mycelium by filtration on Miracloth (Calbiochem), centrifuged and then resuspended at 1.6.10.sup.6 spores/mL. Approximately 16 000 spores are incubated in the presence of the control solution or the A. carterae extract at various concentrations. After incubation for 10 min at room temperature, the spores are placed on a slide for a germination count after 6 hours or on a petri dish for an observation of mycelium growth after 72 hours.

[0605] Tests

Example 4: HPLC Fractionation of Extract D and Test of Antifungal Activity of the Different Fractions Obtained

[0606] In an attempt to characterize which molecules present in the A. carterae extract are responsible for antifungal activity, the bioguided fractionation strategy was selected: the A. carterae extract is fractionated on an HPLC column and tests of biocidal activity against F. graminearum spores are performed for each fraction to determine which fraction contains the molecule(s) responsible for the antifungal activity.

[0607] 200 mg of freeze-dried cells are solubilized in 1 mL of methanol. After centrifugation for 10 min at 4400 rpm, the supernatant is recovered and the total alcohol liquid phase recovered is filtered on paper, the solution is then evaporated in a rotary evaporator at low temperature to collect 48.5 mg of extracted product. An activity test is performed on F. graminearum spores to confirm the activity of the A. carterae extract (FIG. 1A).

[0608] The extract being active, semi-preparative fractionation experiments were performed on a reversed-phase C18 column using a Thermo Scientific Ultimate 3000 high-performance liquid chromatograph according to the following protocol:

[0609] The A. carterae extract was dissolved at 5 g/L in methanol. The following conditions were applied for the extract:

[0610] Flow rate: 2.5 mL/min.

[0611] Column: reversed-phase C.sub.18: L=250 mm; I.D.=10 mm; P.D.=5 μm.

[0612] Injection volume: 150 μL.

[0613] Injection temperature: 24° C.

[0614] Detection wavelength: 280 nm.

[0615] Gradient programme described in Table 7 below.

TABLE-US-00002 TABLE 2 Optimal semi-preparative solvent gradient programme. Time (min) Solvent A (%) Solvent B (%) 0 50 50 25 0 100 40 0 100 43 50 50 48 50 50 Solvent A: Milli-Q water + 0.1% formic acid; Solvent B: Methanol.

[0616] The chromatogram obtained under these conditions is presented in FIG. 1B. Five fractions, F1 to F5, were formed, as described in FIG. 1B, so that each majority peak corresponds to a fraction. Activity tests on F. graminearum growth were performed with 5 mg/ml of each fraction. The results indicate that only fraction F1 still has biocidal activity (FIG. 1C); an MIC of 0.75 mg/ml was determined for this fraction (FIG. 1D).

[0617] Fraction F1 was subjected to a new fractionation according to the following protocol:

[0618] Extract F1 was dissolved at 5 g/L in methanol. The following conditions were applied for extract D: [0619] Flow rate: 2.5 mL/min. [0620] Column: reversed-phase C18: L=250 mm; I.D.=10 mm; P.D.=5 μm. [0621] Injection volume: 150 μL. [0622] Injection temperature: 24° C. [0623] Detection wavelength: 280 nm. [0624] Gradient programme described in Table 8 below

TABLE-US-00003 TABLE 3 Optimal semi-preparative solvent gradient program. Time (min) Solvent A (%) Solvent B (%) 0 30 70 10 15 85 15 15 85 25 0 100 30 0 100 32 30 70 35 30 70 Solvent A: Milli-Q water + 0.1% formic acid; Solvent B: Methanol.

[0625] The chromatogram obtained under these conditions is presented in FIG. 2A. Five fractions, F1-1 to F1-5, were formed, as described in FIG. 2A, the majority peak corresponding to fraction F1-2. Activity tests on F. graminearum growth were performed with 5 mg/ml of each fraction. The results indicate that only fractions F1-2 and F1-3 have biocidal activity (FIG. 2B); an MIC of 0.75 mg/ml was determined for fraction F1-2 (FIG. 2C).

Example 5: Mass Spectrometric Analysis of Fraction F1-2

[0626] To better characterize the molecule present in fraction F1-2, a mass spectrometric analysis was performed under the following conditions:

[0627] The experiments were performed in infusion mode on a QStar Elite spectrometer (Applied Biosystems).

[0628] Ionization mode: Positive-mode electrospray (ESI) Electrospray needle voltage: 4500 V at room temperature Injection conditions: 20 μL of sample dissolved in methanol, with a methanol flow rate of 400 μL/min

[0629] Scan range: 100 to 2000 daltons

[0630] FIG. 3A shows the mass spectrum acquired by positive-mode electrospray ionization on the molecule of interest collected F1-2.

[0631] The exact mass determined is 1381.8276 Daltons. It corresponds to a sodium adduct formed during ionization ([M+Na].sup.+). After subtracting the mass of sodium, 23 daltons, the mass of the molecular peak of the compound is 1358.8 Da.

[0632] A thorough analysis of the exact mass makes it possible to determine one or more empirical formulas related to this mass, with an error of 5 ppm. After rejecting unrealistic proposals, the empirical formula selected is C71H122024.

[0633] A thorough analysis by tandem mass spectrometry was performed on this peak at 1381.8276 Da. The mass spectrum is presented in FIG. 3B. Several peaks (circled peaks—FIG. 3B) are similar to the peaks resulting from the fragmentation of amphidinol 18 (7).

Example 6: Nuclear Magnetic Resonance (NMR) Analysis of Fraction F1-2

[0634] To determine the structure of the molecule with a molecular weight of 1358.8 Da, an NMR analysis was performed according to the following procedure:

[0635] Samples corresponding to peak F1-2 were collected and then completely dissolved in about 350 μL of deuterated methanol (MeOD.sub.4).

[0636] The experiments were performed on a Bruker Avance 14.1 T spectrometer equipped with a multinuclear probe. One- and two-dimensional proton and carbon spectra were acquired using pulse sequences available from the Bruker sequence library.

[0637] The acquisition conditions are as follows: [0638] .sup.1H: Number of scans: 512; Pulse: 8 μs; Acquisition: 5.0 s; Relaxation: 1.0 s [0639] .sup.13C DEPT135: Number of scans: 44666; Pulse: 12 μs; Acquisition: 1.0 s; Relaxation: 3.0 s [0640] HSQC: Number of scans: 64; 512 increments [0641] HMBC: Number of scans: 48; 512 increments [0642] COSY: Number of scans: 56; 256 increments [0643] TOCSY: Number of scans: 48; 256 increments

[0644] The .sup.13C DEPT135 sequence is an experiment for sorting carbons according to the number of directly bound protons: CH.sub.3 and CH>0 and CH.sub.2<0.

[0645] The correlation spectroscopy (COSY) sequence is a 2D homonuclear experiment for identifying protons in scalar interaction spaced 2 or 3 bonds apart.

[0646] The total correlation spectroscopy (TOCSY) sequence is a 2D homonuclear experiment for identifying protons in scalar interaction spaced 3 or more bonds apart.

[0647] The heteronuclear single quantum correlation (HSQC) sequence is a 2D heteronuclear experiment that shows the direct interactions between a carbon and the directly linked proton(s).

[0648] The heteronuclear multiple bond correlation (HMBC) sequence is a 2D heteronuclear experiment that shows the correlations between protons and carbons separated by intervals of 2 or 3 bonds.

[0649] The 1D spectra were processed by a Fourier transform. The spectra were processed by a Fourier transform in both dimensions.

[0650] Based on the results obtained, the acquired .sup.1H spectrum, shown in FIG. 4A, shows a series of peaks distributed over a large spectral window comprised between 1 and 6 ppm. This confirms that the compound studied contains aliphatic and olefinic protons. These shifts also suggest the presence of heteroatoms such as oxygen.

[0651] The .sup.13C DEPT135 spectrum (FIG. 4B) shows a series of peaks in the spectral window comprised between 13 and 211 ppm. The HMBC and HSQC 2D sequences show how the carbons are chained together. The COSY and TOCSY 2D sequences confirm the structural sequence based on proton shifts and correlations.

[0652] The number of unsaturations and rings observed is consistent with that calculated for the molecule on the basis of its empirical formula (=11):

N.sub.i=(2n.sub.c+2−n.sub.H+n.sub.N−n.sub.X)/2

With: n.sub.c: the number of carbon atoms, n.sub.H: the number of hydrogen atoms, n.sub.N: the number of nitrogen atoms, n.sub.x: the number of halogen atoms.

[0653] The 11 unsaturations are distributed as follows: [0654] 1 ketone function [0655] 8 double bonds, including 2 chain-end [0656] 2 rings

[0657] The COSY and TOCSY sequences made it possible to reconstruct the entire carbon skeleton of the structure. These correlations are indicated by links in bold in FIG. 5. These results show that the secondary structure of the molecule corresponds to that of amphidinol 18. The overall interpretation was confirmed by comparing the results obtained in this study with those found in the literature (7).

[0658] In conclusion, all results obtained by nuclear magnetic resonance and mass spectrometry confirm that the molecule present in fraction F1-2, obtained after fractionation of extract D, and which has antifungal activity against F. graminearum, is the amphidinol 18 molecule whose specific chemical data are as follows: [0659] Empirical formula: C.sub.71H.sub.122O.sub.24 [0660] Molar mass: 1358.83 g.Math.mol.sup.−1

REFERENCES

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