WO2018224675A1 - Utilisation d'un amphidinol pour son activite fongicide et/ou bactericide sur les champignons, les oomycetes et/ou bacteries pathogenes des plantes et semences de culture - Google Patents
Utilisation d'un amphidinol pour son activite fongicide et/ou bactericide sur les champignons, les oomycetes et/ou bacteries pathogenes des plantes et semences de culture Download PDFInfo
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- WO2018224675A1 WO2018224675A1 PCT/EP2018/065224 EP2018065224W WO2018224675A1 WO 2018224675 A1 WO2018224675 A1 WO 2018224675A1 EP 2018065224 W EP2018065224 W EP 2018065224W WO 2018224675 A1 WO2018224675 A1 WO 2018224675A1
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/03—Algae
Definitions
- amphidinol for its fungicidal and / or bactericidal activity on fungi, oomvetes and / or pathogenic bacteria of plants and cultured seeds
- the invention relates to the field of seed antifungals and anti-bactericides.
- Fusarium wilt is associated with a species complex comprising two genera of phytopathogenic fungi, Fusarium and Microdochium (1). These two genera include about 19 species capable of inducing fusariosis of the ear of wheat.
- the most common species in Europe are F. graminearum, F. culmorum, F. avenaceum, F. poae, M. nivale and M. majus.
- the genus Fusarium belongs to the division Ascomycetes and the family Nectriaceae.
- the genus Microdochium belongs to the family Tuberculariaceae and includes two species, M. nivale and M. majus, causing the same symptoms on ear and leaves as Fusaria.
- Several fusarium species, of which Fusarium graminearum is the most represented, can be found together the scale of the region, of the plot or on the same ear thus forming the Fusarium complex.
- the severity, incidence and prevalence of each species vary according to geographical location, climatic variations and cultural practices. The presence on the same ear of several of these species is likely to change their balance and their dynamics of toxin production. Fusarium wilt can devastate a crop a few weeks before harvest.
- Septoria Septoria is a wheat disease that causes significant yield losses and causes the most economic losses in the world, especially in humid temperate regions.
- Two main forms of septoria can be distinguished: Septoria leaf spot (Phaeosphaeria nodorum) and leaf septoria (Mycosphaerella graminicola).
- the septoriose of the ears is mainly present in the continental areas whereas that of the leaves is mainly present in the north-west and on the maritime borders where the mushroom finds climatic conditions favorable to its development.
- the symptoms caused by M graminicola appear successively in the form of chlorosis, spots of light green color, before evolving into brownish spots called necroses. These necroses eventually merge into each other (coalescence).
- M. graminicola is a hemibiotropic fungus establishing a first biotrophic phase where the infection takes place on living tissues and then occurs during the necrotrophic phase during which the fungus expresses toxins producing the death of the colonized tissues. Depending on the environmental conditions, reproduction of M. graminicola is sexual in nature (ascospore production) or asexual (production of pycnidiospores).
- Ascospores disseminated by wind over long distances, contribute in particular to the survival of the fungus in the absence of a host plant and is considered as the main source of primary inoculum to initiate the disease.
- Pycnidiospores for their part, are mostly produced during the epidemic phase of the disease during several successive infectious cycles. These spores are dispersed over short distances by the action of splashing raindrops. The decline in potential yields is all the more important as the last leaves under the ear involved in grain filling are severely affected by the disease. Yield losses due to septoria disease have been estimated at 1-2 t.ha- 1 on average, with cases as high as 3-3.5 t.ha- 1 , which represents a 40% decrease in yields. Control methods for controlling M.
- graminicola are based on the use of fungicide and resistant cultivars.
- fungicide efficacy due to a strong selection of pathogens with, for example, resistance to the strobilurin family as well as a recent loss of triazole efficacy in the field. .
- the diseases of the vine nowadays, the vine is cultivated all over the world playing a central role in the economy of many countries. It is consumed in table grapes and juices, but its main exploitation is in the wine industry.
- the European Union is the largest wine producer in the world and the world 's largest exporter of wine products. The sector thus contributes about 15 billion euros a year to the economy of the European Union (www.cev.be).
- the French vineyard covered nearly 865,000 ha, or nearly 3% of arable land and allows France to be the world's largest wine producer with 51.1 million hectoliters.
- the vine has to face many attacks of pathogens including fungal diseases.
- the slow form is characterized by specific leaf colorings: yellowish internervary spots on white varieties and bordered with red on black grape varieties, the remaining green veins. These tasks progress gradually to browning and drying out. Foliar symptoms of the slow form can be visible one year on one vine and disappear the following year.
- the apoplectic form is characterized by rapid drying of aerial organs, branches, leaves and clusters of part or all of the vine stock. This symptom usually occurs when summers are hot, causing the vines to die in just a few days without warning symptoms.
- the variety of sources of inoculum and the very slow and non-visible development of fungi in the vine make the implementation of control methods very complicated.
- Gray mold is a fungal disease caused by an ascomycete fungus called Botrytis cinerea. It belongs to the class of Leotiomycetes, to the order Helotiales and the family Sclerotiniaceae.
- B. cinerea is a necrotrophic fungus capable of colonizing healthy plant tissue, already infected, as well as dead tissue (saprophytism). On leaf, the symptoms appear as brown spots with a greyish felting on the underside (fructifications of the mushroom) which tend to increase and invade the whole limb. Clusters can be affected before flowering and dry out.
- the two diseases that are most severely affecting vineyards today are downy mildew and powdery mildew.
- the causal agent of downy mildew, oomycete Plasmospora viticola belonging to the peronospore order, is a mandatory parasite; to keep it alive and multiply it, it is obligatory to propagate it on surviving vine leaves.
- P. viticola attacks all the herbaceous tissues of the vine as well as clusters. It causes defoliation, browning and drying of berries and stems.
- downy mildew can devastate up to 75% of the crop of the season.
- the life cycle of P. viticola includes a sexual phase and an asexual phase.
- the asexual phase leads to the production of spores necessary for secondary infections and dispersal of the pathogen over a short distance, while the sexual phase produces quiescent and cold-resistant oospores allowing the passage of winter and infections.
- the first macroscopic evidence for the presence of late blight in a vineyard is the appearance of pale yellow spots and irregular (oil stains) magnifying on the upper or adaxial face, leaves.
- the fight against mildew is mainly organized by preventive measures by fungicide sprays. If it is possible to stop an attack, the damage, once caused on the inflorescences and clusters, are irremediable. Powdery mildew
- the powdery mildew of the vine (Erysiphe necator) is a biotrophic obligate ascomycete belonging to the order Erysiphales.
- the fungus colonizes the surface of all the green organs of the vine, especially the upper surface of the leaves, and spreads on the berries.
- a sexual phase that is characterized by the production of cleistothecia containing ascospores can alternate with an asexual phase leading to the formation of conidiophores carrying conidiophores.
- the fungus survives as hyphae in dormant buds or cleistothecia on the surface of the plant.
- the spores contained in the cleistothecia will be released in the spring to germinate on the surface of the buds and young leaves.
- a primary hypha then develops on the leaf surface, then an increasingly complex and branched mycelial network lines the leaf surface.
- conidiophores differentiate from the mycelium constituting the beginning of the sporulation stage and colonize other green tissues of the plant giving rise to secondary infections.
- the presence of conidial mycelium and conidiophores on the surface of infected host tissues gives a powdery, greyish-white appearance. White felting develops on the flower buds that dry out. Only young berries with a sugar level ⁇ 8% are sensitive to powdery mildew. All leaf surfaces may be susceptible to infection, regardless of age.
- Infected young leaves first turn dark green, then the leaves deform and become stunted.
- the upper surface of the leaves may have lighter, chlorotic spots that resemble the stains of late blight oil.
- the health pressure is therefore particularly strong in viticulture. Fungicide treatments intended mainly to control downy mildew and powdery mildew are applied according to a specific schedule to prevent damage due to the appearance of a disease.
- the European Union (EU) employs around 68 000 tonnes of fungicides a year to control vine diseases, which accounts for 65% of the fungicides used in agriculture, while only 3.3% of the EU is occupied by vines (Eurostat, 2007).
- EU European Union
- Apple scab Apple scab is one of the main fungal diseases of the apple tree (genus Malus) with monilia and powdery mildew. It is caused by an ascomycete fungus called Venturia inaequelis, of which there are several thousand strains, causing black or brown lesions on the surface of leaves, buds or fruits and sometimes even on the wood. The fruits and the lower part of the leaves are especially sensitive.
- the fungus overwinters on leaves that fall from infected trees in the form of perithecia.
- the perithecia are filled with ascospores.
- Ascospores are ejected into the air of the orchard during wet days and reach the trees through air movement. This discharge of ascospores begins at budbreak and continues for 6 to 10 weeks, most often until the end of June.
- the ascospores reach the foliage and the leaves are wet for some time, they germinate and penetrate the leaves: there is then primary infection.
- the fungal infection becomes visible in one to three weeks on different parts of the tree. Dark olive or brown spots of about 5 mm appear on the leaves and may eventually cover the entire leaf. Infected flowers may fall. Fruit infection is first recognized by gray spots on the stem.
- conidia are another form of reproductive structure.
- conidia escape there is secondary infection. Conidia can infect any part of the tree and those produced in late summer can even grow on stored fruits. The heavy rain is responsible for dispersing the conidia.
- the disease rarely kills its host but can significantly reduce (up to 100%) fruit quality and production in the absence of fungicide treatment.
- the control strategy requires effective action in the spring to prevent the released spores from infecting or developing on trees.
- the traditional method of protection was to begin fungicide application at budbreak and repeat treatments every seven days until the end of June to protect new growth. Apple orchards are the most treated fungicides and insecticides with an average of 28.8 fungicide treatments per year, of which 19 are dedicated to scab (data IN A).
- bacteria bacteria
- microalgae algae
- invertebrates a source of new bioactive molecules and which are still little exploited
- marine microorganisms accumulate bioactive secondary metabolites whose unique structure is not found in terrestrial organisms. These metabolites therefore potentially represent new molecules of interest.
- Certain substances derived from marine organisms have been described as having antifungal activity or a natural defense substance activity, but the search for these molecules is still very little developed (3).
- Microalgae are unicellular organisms that play a key role in aquatic ecosystems. Producing organic material, they play an important ecological role as they form the basis of the marine food chain. However, their enormous ability to colonize all the world's oceans suggests that they have probably developed effective strategies for controlling pathogens, particularly through the production of natural pesticides. For example, the abundant proliferation in coastal areas of microalgae producing biotoxins is responsible for the formation of toxic algal blooms (HABs) with a significant effect on the trophic cascade.
- HABs toxic algal blooms
- dinoflagellates belonging to the order Gymnodiniales and the family Gymnodiniaceae are present in temperate and tropical marine waters living in free form or in symbiosis with invertebrates (for example, corals).
- Dinoflagellates synthesize a large number of secondary metabolites of the polyketide type (compounds having a biological or pharmacological activity that may be toxic in order to confer a survival advantage), several of which have been characterized, including those responsible for HABs (4).
- the model species of dinoflagellates, Amphidinium carterae produces a profusion of different bioactive compounds, many of which have become so developed as therapeutic agents (5).
- amphidinols are polyhydroxy-polyenes (long chain ployctides) which exhibit strong anti-fungal and hemolytic activity. They thus increase the membrane permeability by associating with the membrane lipids (6).
- compounds similar to amphidinols having a long polyhydroxy chain have been isolated such as lingshuiols, karatungiols, carteraol E, luteophanols, colopsinols, and amphezonol A (5).
- amphidinol 18 one of the molecules responsible for the fungicidal effect of a cell extract of Amphidinium carterae on many plant pathogenic fungi is amphidinol 18.
- a first subject of the invention relates to the use of the molecule of formula (I) below:
- ⁇ i is selected from the group consisting of:
- R 4 represents H or OH
- n is equal to 0 or 1 and
- n 0 or 1
- ⁇ 2 is selected from the group consisting of: and for its fungicidal and / or bactericidal activity on fungi, oomycetes and / or pathogenic bacteria of plants and crop seeds.
- Another subject of the invention relates to a method for controlling fungi, oomycetes and / or pathogenic bacteria of plants and crop seeds comprising the application to the crop plants and / or the coating of said seeds of the molecule. of formula (I).
- a first subject of the invention relates to the use of the molecule of formula (I) below
- R 4 represents H or OH
- n is is equal to 0 or 1
- n 0 or 1
- RI is:
- R2 is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
- the molecule of formula (I) is amphidinol 18 or amphidinol 19:
- Amphidinol 19 The molecule of formula (I) is an amphidinol.
- the molecule of formula (I) may be synthetic or extracted from cells of one or more microalgae of the genus Amphidinium.
- Suitable Amphidiniums 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 diverentum, Amphidinium cra
- the molecule of formula (I) is extracted from Amphidinium carterae.
- the Amphidinium carterae strain used according to the invention is CCMP 1314, AC208 or AC792.
- Said extract may be prepared by any method of cell extraction known to those skilled in the art, solid-liquid or liquid-liquid, for example an extraction in inorganic or organic solvent, which may be chosen from the group consisting of water , aqueous solutions, hydrocarbon solvents (aliphatics, aromatics), oxygenated solvents (alcohols, ketones, acids, esters and ethers), halogenated solvents (dichloromethane, cholerform) and mixtures in any miscible proportion of these solvents.
- inorganic or organic solvent which may be chosen from the group consisting of water , aqueous solutions, hydrocarbon solvents (aliphatics, aromatics), oxygenated solvents (alcohols, ketones, acids, esters and ethers), halogenated solvents (dichloromethane, cholerform) and mixtures in any miscible proportion of these solvents.
- the solvent is water or oxygenated solvents, preferably alcohols, particularly preferably C1 to C4 alcohols such as methanol or ethanol.
- alcohols particularly preferably C1 to C4 alcohols such as methanol or ethanol.
- C1 to C4 alcohols are preferred.
- said extract is a water-soluble fraction.
- the molecule of formula (I) is used in an amount of between 0.1 and 5 mg / ml, preferably between 0.5 and 3 mg / ml, particularly preferably between 0.75 and 1 mg / mL.
- This fungicidal activity on fungi and / or pathogenic oomycetes of plants and crop seeds may in particular be exercised by inhibition of spore germination or by inhibition of growth of the fungus and / or oomycetes.
- the activity is exerted by a lytic activity of the cell walls and membranes which results in cell lysis.
- Cultivating plants are in particular chosen from the group consisting of cereals such as wheat, corn, barley, rice, soya, fruits and vegetables such as potatoes, carrots, apples, peaches, apricots, tomatoes, radishes, beans, vines and ornamental plants.
- cereals such as wheat, corn, barley, rice, soya
- fruits and vegetables such as potatoes, carrots, apples, peaches, apricots, tomatoes, radishes, beans, vines and ornamental plants.
- Said cultivation plants are in particular chosen from the group consisting of the genera Abelmoschus, Acacia, Achras, Agave, Agrostis, Aleurites, Allium, Anacardium, Pineapple, 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, Dactyl
- the plant pathogenic fungi and crop seeds are ascomycetes or basidiomycetes, preferably ascomycetes.
- the said pathogenic fungi of plants and crop seeds are pathogenic fungi of plants and crop seeds of the following types:
- Acrocalymma Acrocalymma medicaginis, 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.
- Botrytis Botrytis, Botrytis allii, Botrytis anthophila, Botrytis cinerea, Botrytis fabae, Botrytis narcissicola,
- Claviceps Claviceps fusiformis, Claviceps purpurea, Claviceps sorghum, Claviceps zizaniae,
- Oculimacula Oculimacula acuformis, Oculimacula yallundae, Blumeria, Blumeria graminis,
- Pyrenophora Pyrenophora avenae, Pyrenophora chaetomioides, Pyrenophora graminea, Pyrenophora seminiperda, Pyrenophora teres, Pyrenophora teres f. maculata, Pyrenophora teres f. teres, Pyren ophora tritici-repen tis,
- 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,
- Rhynchosporium Rhynchosporium secalis
- Microdochium Microdochium oryzae
- Pezzicula Pezzicula alba, Pezzicula malicorticis,
- Puccinia 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 schedon
- Venturia Venturia inaequalis. Venturia carpophila, Acrodontium, Acrodontium simplex,
- Albonectria Albonectria rigidiuscula, Allodus, Allodus podophylli, Amphobotrys, Amphobotrys ricini, Anguillosporella, Anguillosporella vermiformis, Anthostomella, Anthostomella pullulons,
- Antrodia Antrodia albida, Antrodia serialiformis, Antrodia serialis,
- Ascochyta Ascochyta asparagina, Ascochyta bohemica, Ascochyta caricae, Ascochyta doronici, Ascochyta fabae f.sp. lentis, Ascochyta graminea, Ascochyta hordei, Ascochyta humuli, Ascochyta pisi, Ascochyta prasadii, Ascochyta sorghi, Ascochyta spinaciae, Ascochyta tarda, Ascochyta tritici,
- Asteroma Asteroma caryae
- Athelia Athelia arachnoidea, Athelia rolfsii,
- Aurantiporus Aurantiporus fissilis
- Biscogniauxia Biscogniauxia capnodes, Biscogniauxia marginata,
- Botryosphaeria Botryosphaeria, Botryosphaeria cocogena, Botryosphaeria dothidea, Botryosphaeria marconii, Botryosphaeria obtusa, Botryosphaeria rhodina, Botryosphaeria ribis, Botryosphaeria stevensii, Botryosporium, Botryosporium pulchrum, Botryotinia, Botryotinia fuckeliana, Botryotinia polyblastis, Boxwood blight, Brachybasidiaceae, Brasiliomyces, Brasiliomyces malachrae, Briosia, Briosia ampelophaga, Brown ring patch, Buckeye rot of tomato, Bulbomicrosphaera, Cadophora, Cadophora malorum, Caespitotheca,
- Calonectria Calonectria ilicicola, Calonectria indusiata, Calonectria kyotensis, Calonectria pyrochroa, Calonectria quinqueseptata
- Camarotella Camarotella acrocomiae, Camarotella costaricensis, Canna rust,
- Capitorostrum Capitorostrum cocoes
- Ceratocystis 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, Ceratorhiza, Ceratorhiza hydrophila
- Cercoseptoria Cercoseptoria ocellata, Cercosporella, Cercosporella rubi Ceriporia, Ceriporia spissa, Ceriporia xylostromatoides, Cerrena, Cerrena unicolor, Ceuthospora, Ceuthospora lauri,
- Choanephora Choanephora cucurbitarum, Choanephora infundibulifera, Chrysanthemum, Chrysanthemum white rust, Chrysomyxa, Chrysomyxa cassandrae,
- 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, Cladosporium, Cladosporium arthropodii, Cladosporium cladosporioides, Cladosporium cladosporioides f.sp. pisicola, Cladosporium cucumerinum, Cladosporium herbarum, Cladosporium herbarum, Cladosporium herbarum, Cladosporium herbarum
- Coprinopsis Coprinopsis psychromorbida, Cordana, Cordana johnstonii, Cordana musae, Coriolopsis floccosa,
- Crinipellis Crinipellis sarmentosa, Cronartium, Cronartium ribicola, Cryphonectriaceae, Cryptobasidiaceae, Cryptocline, Cryptocline cyclaminis, Cryptomeliola,
- Cryptosporella Cryptosporella umbrina, Cryptosporiopsis, Cryptosporiopsis tarraconensis, Cryptosporium, Cryptosporium minimum,
- Curvularia Curvularia, Curvularia lunata, Curvularia caricae-papayae, Curvularia penniseti, Curvularia senegalensis, Curvularia trifolii,
- Cyclaneusma needle cast Cylindrocarpon
- Cylindrocarpon ianthothele var. ianthothele
- Cylindrocarpon magnusianum Cylindrocarpon musae
- Cylindrocladiella Cylindrocladiella camelliae, Cylindrocladiella parva
- Cytospora Cytospora palmarum, Cytospora personata, Cytospora sacchari, Cytospora sacculus, Cytospora terebinthi,
- Cytosporina Cytosporina ludibunda, Dactuliophora, Dactuliophora elongata,
- Discosia Discosia artocreas, Discostroma, Discostroma corticola,
- Distocercospora Distocercospora livistonae
- Dothiorella Dothiorella, Dothiorella brevicollis, Dothiorella dominicana, Dothiorella dulcispinae, Dothiorella gregaria,
- Drechslera Drechslera, Drechslera avenacea, Drechslera campanulata, Drechslera dematioidea, Drechslera gigantea, Drechslera glycines, Drechslera musae-sapientium, Drechslera teresf. maculata, Drechslera wirreganensis,
- Eballistra Eballistra lineata, Eballistra oryzae, Eballistraceae,
- Entyloma Entyloma ageratinae, Entyloma dahliae, Entyloma ellisii, Epicoccum, Epicoccum nigrum,
- Exobasidiaceae Exobasidium burtii, Exobasidium reticulatum, Exobasidium vaccinii var. japonium, exobasidium vaccinii-uliginosi, exobasidium vexans, xxophiala alkalophila, 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 phaeomuriform
- Galactomyces Galactomyces candidum, Ganoderma, Ganoderma brownii, Ganoderma lobatum, Ganoderma megaloma, Ganoderma meredithiae, Ganoderma orbiforme, Ganoderma philippii, Ganoderma sessile, Ganoderma tornatum, Ganoderma zonatum,
- Geastrumia Geastrumia polystigmatis
- Geotrichum Geotrichum candidum, Geotrichum klebahnii, Gibberella, Gibberella acuminata, Gibberella avenacea, Gibberella baccata, Gibberella cyanogena, Gibberella fujikuroi, Gibberella intricans, Gibberella pulicaris, Gibberella stilboides, Gibberella tricincta, Gibberella xylarioides, Gibberella zeae,
- Gliocladiopsis Gliocladiopsis tenuis, Gliocladium, Gliocladium vermoeseni, Gloeocercospora, Gloeocercospora sorghi, Gloeocystidiellum, Gloeocystidiellum porosum,
- Gloeophyllum Gloeophyllum mexicanum, Gloeophyllum trabeum, Gloeoporus, Gloeoporus dichrous,
- Gymnosporangium Gymnosporangium kernianum, Gymnosporangium libocedri, Gymnosporangium nelsonii, Gymnosporangium yamadae,
- Haematonectria Haematonectria haematococca
- Hyphodermella Hyphodermella corrugata, Hyphodontia, Hyphodontia aspera, Hyphodontia sambuci, Hypoxylon, Hypoxylon tinctor,
- Inonotus Inonotus, Inonotus arizonicus, Inonotus cuticularis, Inonotus dryophilus, Inonotus hispidus, Inonotus ludovicianus,
- Leandria Leandria momordicae, Lentinus, Lentinus tigrinus
- Lenzites Lenzites betulina, Lenzites elegans,
- Leohumicola Leohumicola atra, Leohumicola incrustata, Leohumicola levissima,
- Leptosphaerulina Leptosphaerulina crassiasca, Leptosphaerulina trifolii
- Leptothyrium Leptothyrium nervisedum
- Leucocytospora Leucocytospora leucostoma, Leucostoma, Leucostoma auerswaldii, Leucostoma canker, Leucostoma kunzei, Leucostoma persoonii
- Leveillula Leveillula compositarum, Leveillula leguminosarum, Leveillula taurica,
- Linochora Linochora graminis
- Macrophoma Macrophoma mangiferae, Macrophoma theicola
- Melampsora Melampsora United, Melampsora occidentalis, Melanconis, Melanconis carthusiana, Melanconium, Melanconium juglandinum, Meliola, Meliola mangiferae, Meliola zangii, Meruliopsis, Meruliopsis ambigua, Microascus, Microascus brevicaulis,
- Monochaetia Monochaetia coryli, Monochaetia mali, Monographella, Monographella albescens, Monographella cucumerina, Monographella nivalis,
- Mucor Mucor circinelloides, Mucor hiemalis, Mucor mucedo, Mucor paronychius, Mucor piriformis, Mucor racemosus, Mycenae, Mycena citricolor,
- Mycocentrospora Mycocentrospora acerina
- Mycosphaerella Mycosphaerella recutita, Mycosphaerella rosicola, Mycosphaerella rubi, Mycosphaerella stigma-platani, Mycosphaerella striatiformans
- Nemania Nemania broadcast, Nemania serpens,
- Neocosmospora Neocosmospora vasitis, Neodeightonia, Neodeightonia phoenicum
- Neoerysiphe Neoerysiphe galeopsidis
- Neofabraea Neofabraea perennans
- Neofusicoccum Neofusicoccum mangiferae
- Oidiopsis Oidiopsis gossypii, Oidium, Oidium arachidis, Oidium caricae-papayae, Oidium indicum, Oidium mangiferae, Oidium manihotis,
- Ophiobolus Ophiobolus anguillides, Ophiobolus cannabinus, Ophioirenina,
- Oxyporus Oxyporus corticola
- Periconia Periconia circinata, Periconiella, Periconiella cocoes,
- Pestalotia Pestalotia, Pestalotia longiseta, Pestalotia rhododendri, Pestalotiopsis, Pestalotiopsis adjustta, Pestalotiopsis arachidis, Pestalotiopsis disseminata, Pestalotiopsis guepini, Pestalotiopsis leprogena, Pestalotiopsis longiseta, Pestalotiopsis mangiferae, Pestalotiopsis palmarum, Pestalotiopsis sydowiana, Pestalotiopsis theae,
- Peyronellaea Peyronellaea curtisii
- Phaeocytostroma Phaeocytostroma iliau, Phaeocytostroma sacchari
- Phaeoramularia Phaeoramularia heterospora, Phaeoramularia indica, Phaeoramularia manihotis,
- Phaeoseptoria Phaeoseptoria musae, Phaeosphaerella, Phaeosphaerella mangiferae, Phaeosphaerella theae,
- Phaeosphaeriopsis Phaeosphaeriopsis obtusispora
- Phaeotrichoconis Phaeotrichoconis crotalariae, Phialophora, Phialophora asteris, Phialophora cinerescens, Phialophora gregata, Phialophora tracheiphila,
- Phoma glomerata Phoma gleamina, Phoma glabalata, Phoma glabalata, Phoma glabella, Phoma glabarica, Phoma glabella, Phoma macropora, Phoma microspora, Phoma narcissi, Phoma nebulosa, Phoma oncidii-sphacelati, Phoma pinodella, Phoma sclerotioides, Phoma
- Phomopsis cannabina Phomopsis coffeae, Phomopsis ganjae, Phomopsis javanica, Phomopsis longicolla, Phomopsis mangiferae, Phomopsis prunorum, Phomopsis sclerotioides, Phomopsis theae, Phragmidium, Phragmidium mucronatum, Phragmidium rosae-pimpinellifoliae, Phragmidium rubi- idaei, Phragmidium violaceum,
- Phyllachora Phyllachora, Phyllachora banksiae, Phyllachora cannabis, Phyllachora graminis, Phyllachora gratissima, Phyllachora musicola, Phyllachora pomigena, Phyllachora sacchari,
- Phyllosticta 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 penici
- Piricaudiopsis Piricaudiopsis, Piricaudiopsis punicae, Piricaudiopsis rhaphidophorae, Piricaudiopsis rosae, Plenodomus, Plenodomus destruens, Plenodomus meliloti, Pleosphaerulina, Pleosphaerulina sojicola,
- Pleospora Pleospora alfalfae, Pleospora betae, Pleospora herbarum, Pleospora lycopersici, Pleospora tarda, Pleospora theae,
- Podosphaera Podosphaera fuliginea, Podosphaera fusca, Podosphaera leucotricha, Podosphaera macularis, Podosphaera pannosa
- Powdery mildew, Pseudocercospora, Pseudocercospora arecacearum, Pseudocercospora cannabina, Pseudocercospora fuligena, Pseudocercosporella herpotrichoides, Pseudocercospora gunnerae, Pseudocercospora pandoreae, Pseudocercospora puderi, Pseudocercospora rhapisicola, Pseudocercospora theae, Pseudocercospora vitis, Pseudocercosporella capsellae, Pseudocochliobolus, Pseudocochliobolus eragrostidis,
- Pucciniaceae Pucciniastrum, Pucciniastrum americanum, Pucciniastrum arcticum, Pucciniastrum epilobii, Pucciniastrum hydrangeae,
- Ramulispora Ramulispora sorghum, Ramulispora sorghicola, Rhinocladium, Rhinocladium corticola, Rhizophydium, Rhizophydium graminis,
- Rhizopus Rhizopus arrhizus, Rhizopus circinans, Rhizopus microsporus, Rhizopus oryzae, Rhytisma, Rhytisma punctatum, Rhytisma vitis, Rigidoporus, Rigidoporus vinctus,
- Seimatosporium Seimatosporium mariae, Seimatosporium rhododendri,
- Serpula Serpula lacrymans, Setosphaeria, Setosphaeria rostrata, Setosphaeria turcica,
- Stagonospora Stagonospora, Stagonospora avenae, Stagonospora meliloti, Stagonospora recedens, Stagonospora sacchari, Stagonospora tainanensis, Stagonospora
- Stegocintractia Stegocintractia junci, Stemphylium, Stemphylium alfalfae, Stemphylium bolickii, Stemphylium cannabinum, Stemphylium globuliferum, Stemphylium lycopersici, Stemphylium reminderforme, Stemphylium solani, Stemphylium vesicarium,
- Stenella Stenella anthuriicola, Stigmatomycosis,
- Stigmina Stigmina carpophila, Stigmina palmivora, Stigmina platani-racemosae, Stromatinia, Stromatinia cepivora, Sydowiella, Sydowiella depressula, Sydowiellaceae,
- Thielaviopsis Thielaviopsis, Thielaviopsis basicola, Thielaviopsis ceramica, Thyrostroma, Thyrostroma compactum, Tiarosporella, Tiarosporella urbis-rosarum,
- Tilletia Tilletia barclayana, Tilletia caries, Tilletia controversa, Tilletia laevis, Tilletia tritici, Tilletia walkeri,
- Tranzschelia Tranzschelia pruni-spinosae
- Trichoderma Trichoderma koningii, Trichoderma paucisporum, Trichoderma songyi, Trichoderma theobromicola, Trichoderma viride,
- Tubercularia Tubercularia lateritia
- Typhula ishula blight, Typhula idahoensis, Typhula incarnata, Typhula ishikariensis, Typhula variabilis, Ulocladium, Ulocladium consortia, Uncinula,
- Uredo Uredo, Uredo behnickiana, Uredo 4.000eriana, Uredo musae, Uredo nigropuncta, Uredo rangelii, Urocystis, Urocystis agropyri, Urocystis brassicae, Urocystis occulta,
- Urophlyctis Urophlyctis, Urophlyctis leprosides, Urophlyctis trifolii,
- Ustilago Ustilago avenae, Ustilago esculenta, Ustilago hordei, Ustilago maydis, Ustilago nigra, Ustilago nuda, Ustilago scitaminea, Ustilago tritici, Vankya, Vankya ornithogali,
- Veronaea Veronaea musae
- Verticillium Verticillium, Verticillium albo-atrum, Verticillium alfalfae, Verticillium dahliae, Verticillium isaacii, Verticillium klebahnii, Verticillium longisporum, Verticillium nonalfalfae, Verticillium theobromae, Verticillium wilt, Verticillium zaregamsianum,
- the crop plants targeted by the invention are as follows:
- 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 recondita, Puccinia striiformis, Pyrenophora tritici-repentis, Rhizoctonia cerealis, Microdochium and Zymoseptoria tritici
- Cochliobolus miyabeanus Fusarium fijikuro, Magnaporthe oryzae, Microdochium oryzae, Pyricularia oryzae, Rhizoctonia oryzae, Rhizoctonia solani, Sarocladium oryzae, Ustilaginoides virens
- Botrytis cinerea Erysiphe necator, Plasmopara viticola, Guignardia bidwelli, Erisyphe necator, Diplodia seriata
- Cercopora kikuchii Colletotrichum dematium, Corynespora cassiicola, Fusarium graminearum, Pythium spp., Rhizoctonia solani, Sclerotinia sclerotiorum, Septoria wisteria
- Apple tree (Malus domestica) Monilia fructigena, Monilia laxa, Pezzicula alba, Pezzicula malicorticis, Venturia inaequalis
- Botrytis cinerea Strawberry (Fragaria sp)
- Aternaria alternata Alternaria dauci
- Alternaria radicina Peach Pieris persica
- apricot Pieris armeniaca
- the pairs of fungi or bacteria vs. are as follows:
- Vine Botrytis cinerea, Erysiphe necator, Plasmopara viticola, Guignardia bidwelli, Erisyphe necator, Diplodia seriata
- Potato Alternia alternata, Alternaria solani, Phytophtora infestations, Rhizoctonia solani Tomato: Phytophtora infestations
- the invention also relates to a method for controlling fungi, oomycetes and / or pathogenic bacteria of plants and cultured seeds comprising the application to the culture plants of the molecule of formula (I):
- Ri is selected from the group consisting of:
- R 3 represents H or SO 3 Na
- R 4 represents H or OH
- n is equal to 0 or 1
- n 0 or 1
- R2 is selected from the group consisting of
- RI is:
- R 3 is H or SO 3 Na.
- R2 is This struggle can be curative or preventive, preferably curative.
- the application to the crop plants can be carried out by any means known to those skilled in the art to reach the parts of plants affected by the fungus and / or bacteria.
- the molecule of formula (I) is applied at a dose of between 0.1 and 5 mg / ml, preferably between 0.5 and 3 mg / ml, particularly preferably between 0.75 and 1 mg / ml. mL.
- the seed coating can be carried out by any technique known to those skilled in the art that keeps the asset in contact with the seed.
- the coating can be carried out by dusting or spraying.
- the coating may include formulants and adjuvants.
- formulants The purpose of the formulants is to make it possible to apply and maintain the active substance (s) on the grain, in equal and constant proportion throughout the entire application process of the product, and this at very low doses.
- Formulants include: organic solvents or water, dispersants, emulsifiers, surfactants or wetting agents, dyes ...
- Surfactants and emulsifiers have the property of joining together and stably maintaining two incompatible liquids together.
- the pelliculants correspond to the application of a microporous film on the surface of the seed. They do not change the shape or size of the seed. They improve coverage and homogeneity of treatment. When the seeds are used by the farmer, they improve the user's comfort at the time of sowing by removing dust and facilitating the flow of seeds into the seed drill. They improve the action of the active substance (s) in culture condition. The enrobants change the shape, size and weight of the seed. They improve the precision of the sowing.
- the methods for controlling the fungi and / or pathogenic bacteria of the plants and treatment culture seeds according to the invention are particularly suitable against a fusarium, preferably a fusarium, cited in Table 1.
- Fusarium oxysporum f. sp. cucumerinum FUSACC Cucumber neck Fusarium wilt Gibberella fujikuroi GIBBFU Fusarium wilt Albonectria rigidiuscula CALORI Fusarium wilt Gibberella stilboides GIBBST Fusarium wilt Fusarium oxysporum f. sp. carthami FUSACA Fusarium head blight Gibberella baccata GIBBBA Fusarium head blight
- GIBBFS Fusarium wilt Gibberella zeae GIBBZE Fusarium wilt Fusarium oxysporum f. sp. elaeidis FUSAEL Disease Name Pathogen Code OEPP Fusarium wilt Fusarium oxysporum f. sp. wisteria FUSAGY Fusarium wilt Fusarium oxysporum f. sp. tracheiphilum FUSAT Fusarium tuberosity of the
- the methods for controlling fungi, oomycetes and / or pathogenic bacteria of the plants and treatment culture seeds according to the invention are particularly suitable for fungi or bacteria vs. bacteria. following crop plants:
- 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 marine microorganism bank of Roscoff (RCC: Roscoff Culture Collection). These microalgae are grown in Ll artificial seawater (https://ncma.bigelow.org/algal-recipes) at 19 ° C with a day / night cycle of 12H / 12H. The luminous intensity used is 100 ⁇ . The biomass is recovered at the end of the exponential phase of growth by centrifugation (15 min at 3000 RPM).
- the cell pellet obtained is frozen and then subjected to lyophilization using a laboratory freeze-dryer (Alpha 1-2 LDplus, labconco) in order to stably keep the active ingredient for a long time. After lyophilization, the dry matter is weighed.
- a laboratory freeze-dryer Alpha 1-2 LDplus, labconco
- Example 3 Germination Test of Fusarium graminearum
- the spores of Fusarium graminearum are grown in the depleted "Mung bean" medium.
- the spores are separated from the mycelium by filtration on miracloth (Calbiochem), centrifuged and then resuspended at 1.6 ⁇ 10 6 spores / ml.
- About 16,000 spores are incubated in the presence of the control solution or A extract. carterae at different concentrations. After incubation for 10 min at room temperature, the spores are placed on a coverslip for germination count after 6H or on a petri dish for observation of mycelium growth after 72H.
- the bioguidative fractionation strategy was chosen: the A. carterae is fractionated on an HPLC column and biogenic activity tests against F. graminearum spores are performed for each fraction to determine which fraction contains the molecule (s) responsible for the anti-fungal activity. .
- Injection temperature 24 ° C.
- Solvent A MilliQ water + 0.1% formic acid
- Solvent B Methanol
- FIG. 1B The chromatogram obtained under these conditions is shown in FIG. 1B.
- Activity tests on the growth of F. graminearum were performed with 5 mg / ml of each fraction.
- the results indicate that only the fraction F1 still has the biocidal activity (FIG. 1C), a MIC of 0.75 mg / ml could be determined for this fraction (FIG. 1D).
- the fraction F1 was subjected to a new fractionation according to the following protocol:
- the F1 extract was dissolved at 5 g / L in methanol. The following conditions have been applied for extract D:
- Injection temperature 24 ° C.
- FIG. 2A The chromatogram obtained under these conditions is presented in FIG. 2A.
- Activity tests on the growth of F. graminearum were performed with 5 mg / ml of each fraction.
- the results indicate that only the Fl-2 and Fl-3 fractions possess the biocidal activity (Figure 2B), a MIC of 0.75 mg / ml could be determined for the Fl-2 fraction ( Figure 2C).
- Electrospray needle voltage 4500 V at room temperature
- Figure 3A shows the mass spectrum acquired in electrospray ionization in positive mode on the molecule of interest collected Fl-2.
- the exact mass determined is 1381.8276 Daltons. It corresponds to a sodium adduct formed during ionization ([M + Na] + ). After deducting the sodium mass of 23 Daltons, the mass of the molecular peak of the compound is 1358.8 Da.
- NMR analysis was carried out according to the following procedure: The samples corresponding to the Fl-2 peak were collected and then were completely dissolved in about 350 ⁇ of deuterated methanol (MeOD 4 ).
- HSQC Number of scans: 64; 512 increments
- HMBC Number of scans: 48; 512 increments - COZY: Number of scans: 56; 256 increments
- TOCSY Number of scans: 48; 256 increments
- the 13 C DEPT135 sequence is an experiment that sorts the carbons according to the number of directly bound protons: CH3 and CH> 0 and CH2 ⁇ 0.
- the sequence COSY Correlation SpectroscopY
- the sequence TOCSY Total Correlation SpectroscopY
- the sequence TOCSY is a homonuclear 2D experiment that allows to identify protons in scalar interaction spaced by 3 or more bonds.
- the HSQC (Heteronuclear Single Quantum Correlation) sequence is a heteronuclear 2D experiment that highlights the direct interactions between a carbon and the directly bound proton (s).
- the HMBC (Heteronuclear Multiple Bond Correlation) sequence is a heteronuclear 2D experiment that highlights the correlations between protons and carbons separated by 2 or 3 distance bonds.
- the 1D spectra were processed by a Fourier transform.
- the spectra were processed by a Fourier transform in both dimensions.
- the 1 H acquired spectrum shown in Figure 4A, highlights a series of peaks distributed over a broad spectral window between 1 and 6ppm. This confirms that the object compound contains aliphatic and olefinic protons. These displacements also suggest the presence of heteroatoms such as oxygen.
- the 13 C DEPT135 spectrum (FIG. 4B) shows a series of peaks on the spectral window between 13 and 211 ppm.
- the 2D HMBC and HSQC sequences make it possible to highlight the sequence of the carbons between them.
- 2D sequences COZY and TOCSY make it possible to confirm the sequence of the structure from proton displacements and their correlations.
- Ni (2n c + 2 - n H + n N - n x ) / 2
- ne the number of carbon atoms
- n H the number of hydrogen atoms
- n N the number of nitrogen atoms
- n x the number of halogen atoms.
- the 11 unsaturations are divided according to: - 1 ketone function
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Abstract
Description
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Priority Applications (8)
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BR112019025727-6A BR112019025727B1 (pt) | 2017-06-08 | 2018-06-08 | Processo para controlar fungos, oomicetos e/ou bactérias patogênicas de plantas e sementes de cultura |
RU2019144319A RU2790051C2 (ru) | 2017-06-08 | 2018-06-08 | Применение амфидинола с фунгицидной и(или) бактерицидной активностью в отношении грибов, оомицетов и(или) патогенных бактерий растений и семян |
EP18728908.7A EP3634129A1 (fr) | 2017-06-08 | 2018-06-08 | Utilisation d'un amphidinol pour son activite fongicide et/ou bactericide sur les champignons, les oomycetes et/ou bacteries pathogenes des plantes et semences de culture |
US16/620,047 US11278027B2 (en) | 2017-06-08 | 2018-06-08 | Use of an amphidinol for its fungicidal and/or bactericidal activity on fungi, oomycetes and/or pathogenic bacteria of plants and crop seeds |
JP2020518570A JP7248663B2 (ja) | 2017-06-08 | 2018-06-08 | 作物植物及び種子の真菌、卵菌、及び/又は病原性細菌に対するその殺真菌活性及び/又は殺細菌活性のためのアンフィジノールの使用 |
CN201880052003.6A CN111315216B (zh) | 2017-06-08 | 2018-06-08 | 前沟藻醇对作物和种子的致病真菌、卵菌和/或细菌的杀真菌和/或杀细菌活性的用途 |
CA3066485A CA3066485A1 (fr) | 2017-06-08 | 2018-06-08 | Utilisation d'un amphidinol pour son activite fongicide et/ou bactericide sur les champignons, les oomycetes et/ou bacteries pathogenes des plantes et semences de culture |
US17/666,943 US11793197B2 (en) | 2017-06-08 | 2022-02-08 | Use of an amphidinol for its fungicidal and/or bactericidal activity on fungi, oomycetes and/or pathogenic bacteria of plants and crop seeds |
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FR1755115A FR3067221B1 (fr) | 2017-06-08 | 2017-06-08 | Utilisation d'un amphidinol pour son activite fongicide et/ou bactericide sur les champignons, les oomycetes et/ou bacteries pathogenes des plantes et semences de culture |
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US17/666,943 Continuation US11793197B2 (en) | 2017-06-08 | 2022-02-08 | Use of an amphidinol for its fungicidal and/or bactericidal activity on fungi, oomycetes and/or pathogenic bacteria of plants and crop seeds |
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CN (1) | CN111315216B (fr) |
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CN111996232A (zh) * | 2020-08-21 | 2020-11-27 | 中国农业科学院郑州果树研究所 | 基于病原分离鉴定及微孔板法筛选桃软腐病药剂的方法 |
CN112741114A (zh) * | 2021-02-23 | 2021-05-04 | 广西壮族自治区农业科学院 | 一种防治甜瓜根腐病的方法 |
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CN110468057B (zh) * | 2019-09-02 | 2021-09-24 | 昆明理工大学 | 一株植物内生盘双端毛孢属真菌m7sb 41及其应用 |
ES2933630A1 (es) * | 2021-06-22 | 2023-02-10 | Univ Almeria | Formulacion fitosanitaria |
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Non-Patent Citations (11)
Title |
---|
ARSENIUK, E.; FOREMSKA, E.; GORAL, T.; CHELKOWSKI, J.: "Fusarium head blight reactions and accumulation ofdeoxynivalenol (DON) and some of its derivatives in kernels of wheat, triticale and rye", JOURNAL OF PHYTOPATHOLOGY, vol. 147, 1999, pages 577 - 590 |
BOWLER, C.; VARDI, A.; ALLEN, A. E.: "Océanographie and biogeochemical insights from diatom genomes", ANNUAL REVIEW OF MARINE SCIENCE, vol. 2, 2010, pages 333 - 65 |
DEVI P; WAHIDULLA S; KAMAT T; D'SOUZA L: "Screening marine organisms for antimicrobial activity against clinical pathogens", INDIAN J.GEOMAR.SCI., vol. 40, 2011, pages 338 - 346 |
ECHIGOYA R ET AL: "The structures of five new antifungal and hemolytic amphidinol analogs from Amphidinium carterae collected in New Zealand", HARMFUL ALGAE, ELSEVIER, AMSTERDAM, NL, vol. 4, no. 2, 1 February 2005 (2005-02-01), pages 383 - 389, XP027686712, ISSN: 1568-9883, [retrieved on 20050201] * |
GENOVEFFA NUZZO ET AL: "Antifungal Amphidinol 18 and Its 7-Sulfate Derivative from the Marine Dinoflagellate Amphidinium carterae", JOURNAL OF NATURAL PRODUCTS., vol. 77, no. 6, 27 June 2014 (2014-06-27), US, pages 1524 - 1527, XP055400101, ISSN: 0163-3864, DOI: 10.1021/np500275x * |
MAYER AM; RODRIGUEZ AD; TAGLIALATELA-SCAFATI O; FUSETANI N: "Marine pharmacology in 2009-2011: marine compounds with antibacterial, antidiabetic, antifungal, anti-inflammatory, antiprotozoal, antituberculosis, and antiviral activities; affecting the immune and nervous systems, and other miscellaneous mechanisms of action", MAR DRUGS., vol. 11, no. 7, 2013, pages 2510 - 73 |
MORSY N; HOUDAI T; MATSUOKA S; MATSUMORI N; ADACHI S ET AL.: "Structures of new amphidinols with truncated polyhydroxyl chain and their membrane-permeabilizing activities", BIOORGANIC AND MEDICINAL CHEMISTRY, vol. 14, 2006, pages 6548 - 6554, XP025133563, DOI: doi:10.1016/j.bmc.2006.06.012 |
MURRAY S; GARBY T; HOPPENRATH M; NEILAN BA: "Genetic diversity, morphological uniformity and polyketide production in dinoflagellates (Amphidinium, Dinoflagellata", PLOS ONE, vol. 7, no. 6, 2012 |
NUZZO G; CUTIGNANO A; SARDO A; FONTANA A: "Antifungal amphidinol 18 and its 7-sulfate derivative from the marine dinoflagellate Amphidinium carterae", J NAT PROD, 27 June 2014 (2014-06-27) |
WASHIDA K ET AL: "Karatungiols A and B, two novel antimicrobial polyol compounds, from the symbiotic marine dinoflagellate Amphidinium sp", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 47, no. 15, 10 April 2006 (2006-04-10), pages 2521 - 2525, XP025003878, ISSN: 0040-4039, [retrieved on 20060410], DOI: 10.1016/J.TETLET.2006.02.045 * |
YANHUI MENG ET AL: "Structure and Biosynthesis of Amphidinol 17, a Hemolytic Compound from Amphidinium carterae [bottom]", JOURNAL OF NATURAL PRODUCTS., vol. 73, no. 3, 26 March 2010 (2010-03-26), US, pages 409 - 415, XP055415810, ISSN: 0163-3864, DOI: 10.1021/np900616q * |
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CN111996232A (zh) * | 2020-08-21 | 2020-11-27 | 中国农业科学院郑州果树研究所 | 基于病原分离鉴定及微孔板法筛选桃软腐病药剂的方法 |
CN112741114A (zh) * | 2021-02-23 | 2021-05-04 | 广西壮族自治区农业科学院 | 一种防治甜瓜根腐病的方法 |
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FR3067221A1 (fr) | 2018-12-14 |
CN111315216B (zh) | 2022-11-04 |
BR112019025727A2 (pt) | 2020-06-23 |
US20200100499A1 (en) | 2020-04-02 |
US11278027B2 (en) | 2022-03-22 |
US20220192194A1 (en) | 2022-06-23 |
CN111315216A (zh) | 2020-06-19 |
JP2020522581A (ja) | 2020-07-30 |
CA3066485A1 (fr) | 2018-12-13 |
US11793197B2 (en) | 2023-10-24 |
JP7248663B2 (ja) | 2023-03-29 |
EP3634129A1 (fr) | 2020-04-15 |
RU2019144319A (ru) | 2021-07-09 |
RU2019144319A3 (fr) | 2021-09-23 |
FR3067221B1 (fr) | 2020-08-14 |
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