Use of a derivative of hinokitiol for its fungicidal and / or bactericidal activity on fungi, oomycetes and / or pathogenic bacteria of plants and crop seeds
A hinokitiol derivative addresses the ineffectiveness of current wheat disease controls by offering a long-lasting antifungal solution against resistant pathogens, improving crop yield and quality sustainably.
Patent Information
- Application Number
- PCT/EP2025/058586
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-03-28
- Filing Date
- 2025-03-28
- Publication Date
- 2025-10-02
AI Technical Summary
Current methods for controlling wheat diseases like Fusarium wilt and septoria are ineffective due to pathogen resistance and environmental concerns, necessitating a long-lasting, environmentally friendly antifungal alternative.
Utilization of a hinokitiol derivative with specific structural variations for its antifungal and antibacterial activity against pathogenic fungi and bacteria affecting wheat and other crops.
The hinokitiol derivative provides a long-lasting antifungal and antibacterial effect, reducing crop damage and toxin production, thereby enhancing yield and quality while minimizing chemical use.
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Figure EP2025058586_02102025_PF_FP_ABST
Abstract
Description
[0001]Use of a hinokitiol derivative for its antifungal and / or antibacterial activity on fungi, oomycetes and / or pathogenic bacteria of plants and crop seeds TECHNICAL FIELD OF THE INVENTION The invention relates to the field of antifungal and antibacterial agents for plants and seeds. STATE OF THE ART In Europe, several diseases of wheat (Triticum aestivum) are responsible for yield losses or even a deterioration in the health quality of the grains. The most important of these diseases are septoria (Septoria spp.) and fusarium wilt. Fusarium wilt is caused by two genera of phytopathogenic fungi, Fusarium and Microdochium (1). These two genera include approximately 19 species capable of inducing fusarium wilt of the wheat ear. 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 Tuberculariaceae family and includes two species, M. nivale and M. majus, which cause the same symptoms on ears and leaves as Fusaria. Several species of Fusarium, of which Fusarium graminearum is the most represented, can be found together at the regional, plot or single ear scale, 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 of several of these species on the same ear is likely to modify their balance and their toxin production dynamics. Fusarium wilt of wheat can devastate a crop a few weeks before harvest.It can be associated with both significant yield losses (abortion and low grain weight), a reduction in their germination quality or even a decrease in their quality due to the presence of toxins in the grains. Indeed, fungi of the genus Fusarium, but not of the genus Michrodochium, are capable of producing toxic secondary metabolites, mycotoxins, the presence of which increases the incidence of the disease on agricultural production and constitutes a major economic and public health problem. The main means of controlling Fusarium wilt include cultural practices, varietal resistance and chemical control. Currently, few wheat varieties are resistant to Fusarium wilt. Once the crop is established, the use of chemical control is possible but with limited effectiveness. The diversity of pathogens as well as their different sensitivity to active ingredients complicates this control.For example, fungi of the genus Fusarium are sensitive to triazoles, while fungi of the genus Microdochium are sensitive to strobilurins. Septoria is a wheat disease responsible for significant yield losses and which causes the most economic losses in the world, particularly in humid temperate regions. Two main forms of septoria can be distinguished: ear septoria (caused by the fungus Phaeosphaeria nodorum) and leaf septoria (caused by the fungus Mycosphaerella graminicola, also known as Zymoseptoria tritici). In France, ear septoria is mainly present in continental areas, while leaf septoria is mainly present in the northwest and on the maritime borders where the fungus finds favorable climatic conditions for its development. Yield losses attributable to septoria have been estimated at 1–2 t.ha. −1on average, with cases ranging up to 3–3.5 t.ha−1, which represents a 40% reduction in yields. Control methods for M. graminicola are based on the use of antifungals and resistant cultivars. However, recent years have seen a significant loss of antifungal efficacy due to strong selection of pathogens with, for example, resistance to the strobilurin family as well as a recent loss of triazole efficacy in the field. Currently, agriculture must therefore face multiple challenges. Indeed, new cultivation techniques must both ensure sufficient yields to feed the population while avoiding persistent environmental contamination and health problems for consumers. In order to avoid yield losses, the agricultural sector has experienced massive use of chemical inputs in recent decades.This massive use of chemical inputs leads to significant medium- and short-term consequences on human health and environmental balance. Among the chemical inputs used in agriculture, conventional plant protection products are traditionally applied to plants. The use of these products leads to the dispersion of toxic residues causing the appearance of resistant fungal strains, which, by crossing with human pathogens, end up having an impact on human health. Thus, there is a need to develop effective and environmentally friendly methods for the protection of agricultural crops, particularly against pathogens. It is therefore necessary to propose viable and effective alternatives to conventional pesticides.Hinokitiol, also known as β-thujaplicin, is known for its antimicrobial properties, against pathogens responsible for infections in humans, but also against phytopathogens. The chemical structure of hinokitiol is also widely described in the field of agriculture. Hinokitiol is a broad-spectrum antifungal agent, which can be used to combat a large number of phytopathogens responsible for diseases in agricultural and market garden crops. Two Japanese patents dating from 1989 (JP0190104 and JP0190103) refer to the inhibitory power of hinokitiol against the phytopathogenic fungi Helicobasidium mompa (responsible for rotting the cortex of tobacco plant roots) and Rosellinia necatrix (causing white rot of the roots of many host plants such as apple, pear, strawberry, apricot and hops). Furthermore, Morita et al.observed in vitro activity of hinokitiol against the following fungi: Botryotinia fuckeliana, Colletotrichum orbiculare, Colletotrichum lagenarium, Fusariumsolani, Pythium aphanidermatum, Phomopsis obscurans and Thanatephorus cucumeris (MoritaY.,Matsumura E.,Okabe T.,Shibata M.,Sugiura M.,Ohe T.,Tsujibo H.,Ishida N.,Inamori Y., 2003: Biological activity of tropolone. Biol. Pharm. Bull.26: 1487–1490). However, the antifungal activity of hinokitiol is limited in time. Indeed, hinokitiol degrades rapidly leading to the disappearance of its antifungal effect. Thus, there remains a need for a treatment using a composition having a long-lasting antifungal effect without requiring a new application of said composition.Surprisingly, the inventors observed a long-lasting antifungal and / or antibacterial effect of a hinokitiol derivative on numerous fungi and / or oomycetes and / or pathogenic bacteria of plants and crop seeds. SUMMARY OF THE INVENTIONA first subject of the invention relates to the use of a compound of the following formula (I):. with n, X and R as defined below, for its antifungal and / or antibacterial activity on fungi and / or oomycetes and / or bacteria pathogenic to plants and crop seeds. Another subject of the invention relates to a method for combating fungi and / or oomycetes and / or bacteria pathogenic to plants and crop seeds comprising a step of applying a compound of formula (I) according to the invention. Another subject of the invention is a compound of formula (I). BRIEF DESCRIPTION OF THE FIGURES Other characteristics and advantages of the invention will emerge from the detailed description which follows, with reference to the appended drawings, in which: - Figure 1 illustrates example 6 by representing the percentage of leaf surface with symptoms of septoria (necrosis and chlorosis) (A) and level of sporulation (density of pycnidia) on the diseased leaf surfaces (B) for the different formulations tested; - Figure 2 illustrates example 6.These are photographs, obtained under a fluorescence microscope, representative (overall view under a x100 microscope objective) of the epiphytic growth of Z. tritici on treated or untreated wheat leaves;- Figure 3 illustrates example 6. These are photographs, obtained under a fluorescence microscope, representative (zoom on the spores) of the epiphytic growth of Z. tritici on treated or untreated wheat leaves;- Figures 4, 5 and 6 illustrate example 7. These are histograms representing the effect of the series of compounds on the spores of F. solani;- Figures 7, 8 and 9 illustrate example 8. These histograms represent respectively the inhibitory effect of the compounds studied on the bacteria of the strains Erwinia persicina, Erwinia chrysanthemi and Pseudomonas syringae, respectively.DESCRIPTION DETAILED DESCRIPTION OF THE INVENTIONThe present invention therefore relates to the use of a compound of the following formula (I): in which- R representso a (C1-C20)alkyl, a heteroalkyl, a (C1-C20)alkenyl, a (C1-C20)alkynyl, said alkyl, heteroalkyl, alkenyl or alkynyl being optionally substituted by one or more substituents chosen from a halogen atom, an oxo group, a (C1-C8)alkyl, an OH group, a (C1-C6)alkoxy and a (C1-C6)haloalkyl, ora saturated or unsaturated and non-aromatic hydrocarbon-based cyclic or polycyclic system, each ring comprising 3 to 7, preferably 3, 5 or 6 members, and optionally substituted by one or more (C1-C8)alkyls, ora saturated or unsaturated and non-aromatic heterocycle, each ring comprising 3 to 7, preferably 5 or 6 links, and comprising one or more, in particular one or 2, heteroatoms chosen from oxygen, sulfur and nitrogen, and optionally substituted by one or more (C1-C8)alkyls, or an aryl, aryl-(C1-C6)alkyl, heteroaryl, or heteroaryl-(C1-C6)alkyl group,said group being optionally substituted by one or more substituents chosen from a halogen atom, a (C1-C8)alkyl, a (C1-C6)alkoxy and a (C1-C6)haloalkyl,- X is an oxygen atom or an NR' group, with R' representing a hydrogen atom or a (C1-C4)alkyl, and- n is equal to 0 or 1,for its antifungal and / or antibacterial activity on fungi and / or oomycetes and / or pathogenic bacteria of plants and crop seeds.By "(C1-C20)alkyl" group is meant, for the purposes of the present invention, a saturated, linear or branched monovalent hydrocarbon chain, comprising 1 to 20, preferably 1 to 15, even more preferably 1 to 12, carbon atoms. By way of example, mention may be made of the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl groups. Preferably, the (C1-C20)alkyl group is chosen from (C1-C12)alkyl,even more preferably chosen from (C1-C6)alkyl. For the purposes of the present invention, the term "heteroalkyl" group means an alkyl as defined above comprising, within the chain, one or more heteroatoms chosen from oxygen, sulfur, nitrogen or phosphorus. The term heteroalkyl therefore includes (C1-C6)alkoxy groups, corresponding to a (C1-C6)alkyl, linked to the rest of the molecule via an oxygen atom, such as a methoxy, ether groups in which one of the links in the hydrocarbon chain is replaced by an oxygen atom, and ester groups, when one of the links in the hydrocarbon chain is replaced by an oxygen atom and the adjacent position is substituted by an oxo group. According to a particular embodiment, one or more methylene groups of said (C1-C, 20)alkyl is substituted by an oxygen atom, the other atoms of the monovalent hydrocarbon chain being carbon atoms. By "(C1-C20)alkenyl" group is meant, for the purposes of the present invention, an unsaturated monovalent hydrocarbon chain, that is to say comprising one or more double bonds, linear or branched comprising 1 to 20, preferably 1 to 15, even more preferably 1 to 10 carbon atoms. By way of example, mention may be made of methylene, ethylene, propylene or butene groups or even a vinylene (ethenylene) group. Preferably, the (C1-C20)alkenyl group is propylene. By “(C1-C20)alkynyl” group is meant, within the meaning of the present invention, a divalent, linear or branched hydrocarbon chain, comprising 1 to 20, preferably 1 to 15, even more preferably 1 to 10 carbon atoms, and one or more triple bonds, such as, for example, propenylene.For the purposes of the present invention, the term "aryl" group means an aromatic hydrocarbon group, preferably comprising from 6 to 10 carbon atoms, and comprising one or more fused rings, such as, for example, a phenyl or naphthyl group. Advantageously, this is phenyl. For the purposes of the present invention, the term "heteroaryl" group means an aromatic group comprising 5 to 10 cyclic atoms including one or more heteroatoms, advantageously 1 to 4 and even more advantageously 1 or 2, such as, for example, sulfur, nitrogen or oxygen atoms, the other cyclic atoms being carbon atoms. Examples of heteroaryl groups are furyl, thienyl, pyrrolyl, pyridinyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl or indyl.Preferably, the heteroaryl group is a furyl. In certain preferred embodiments, X is an oxygen atom. According to a particular embodiment of the invention, R represents a (C1-C20)alkyl, preferably (C1-C15)alkyl, even more preferably (C1-C12)alkyl, or (C1-C6)alkyl, optionally substituted by one or more substituents chosen from a halogen atom, an oxo group, a (C1-C8)alkyl, an OH group, a (C1-C6)alkoxy and a (C1-C6)haloalkyl, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, 2-ethylpentyl, 2,2-dimethylpropyl or 2-ethylhexyl, in particular a methyl or a hexyl.According to one embodiment, R represents a heteroalkyl, with one or more heteroatoms chosen from oxygen, sulfur, nitrogen or phosphorus, preferably oxygen, optionally substituted by one or more substituents chosen from a halogen atom, an oxo group, a (C1-C8)alkyl, an OH group, a (C1-C6)alkoxy and a (C1-C6)haloalkyl such as methoxyethyl, ethoxyethyl, thiomethylethyl (CH2CH2SCH3) or methyl propanoate.According to a particular embodiment of the invention, R represents a (C1-C. 20)alkenyl, in particular (C1-C15)alkenyl, preferably (C1-C12)alkenyl, and even more preferably (C1-C6)alkenyl, optionally substituted by one or more substituents chosen from a halogen atom, an oxo group, a (C1-C8)alkyl, an OH group, a (C1-C6)alkoxy and a (C1-C6)haloalkyl, such as methylene, ethylene, propylene or butene, preferably propylene. According to a particular embodiment of the invention, R represents a saturated or unsaturated and non-aromatic hydrocarbon-based cyclic or polycyclic system, each ring comprising 3 to 7, preferably 3, 5 or 6 members, and optionally substituted by one or more (C1-C8)alkyls, in particular a cyclopropyl, a cyclobutyl, a cyclopentyl, a cyclohexyl, a menthyl or a cholesterol, preferably a cyclopropyl. According to a particular embodiment of the invention, R represents a heterocycle, saturated or unsaturated and non-aromatic, each cycle comprising 3 to 7,preferably 5 or 6 members, and comprising one or more, in particular one or 2, heteroatoms chosen from oxygen, sulfur and nitrogen, and optionally substituted by one or more (C1-C8)alkyls, in particular a tetrahydropyranyl.According to a particular embodiment of the invention, R is an aryl, aryl-(C1-C6)alkyl, heteroaryl, or heteroaryl-(C1-C6)alkyl group, said group being optionally substituted by one or more substituents chosen from a halogen atom, a (C1-C8)alkyl, a (C1-C6)alkoxy and a (C1-C6)haloalkyl, such as a furyl, a thiofuranyl, a phenyl, a chlorophenyl, a chlorobenzyl or a trifluoromethylbenzyl.According to a particular embodiment of the invention, R represents:- a (C1-C12) alkyl, preferably a (C1-C6) alkyl;- a heteroalkyl;- a saturated or unsaturated and non-aromatic hydrocarbon cyclic or polycyclic system, comprising 1, 2, 3 or 4 rings, each ring comprising 3, 5 or 6 links,andoptionally substituted by one or more (C1-C8)alkyls; or- an aryl, aryl-(C1-C6)alkyl, heteroaryl, or heteroaryl-(C1-C6)alkyl group, said group being optionally substituted by one or more substituents selected from a halogen atom, a (C1-C8)alkyl, and a (C1-C6)haloalkyl, the aryl being a phenyl and the heteroaryl being a 5- or 6-membered heteroaryl. According to a particular embodiment of the invention, the compound of formula (I) comprises a group R chosen from: - methyl, ethyl, n-propyl, iso-propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, 2,2-dimethylpropyl, ethylpentyl, ethylhexyl, methoxyethyl, ethoxyethyl, methyl propanoate, thiomethylethyl, cyclopropyl, cyclohexyl, cyclopentyl, cyclobutyl, propylene, furyl, thiofuranyl, tetrahydropyranyl, phenyl, chloro-phenyl, chlorobenzyl, trifluoromethylphenyl or trifluoromethyl-benzyl,and -n is equal to 0 or 1.According to a particular embodiment of the invention, the compound of formula (I) comprises a group R chosen from:- methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, ethylpentyl, ethylhexyl, methoxyethyl, cyclopropyl, propylene, furyl, phenyl, chlorophenyl, trifluoromethylphenyl, chlorobenzyl or trifluoromethylbenzyl, and -n is equal to 0 or 1.According to a particular embodiment of the invention, the compound of formula (I) comprises a group R chosen from:- methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, in particular methyl, ethyl, propyl, butyl, pentyl, hexyl, and -n is equal to 0 or 1, in particular 0. According to a particular embodiment of the invention, n is equal to 1. According to another particular embodiment of the invention, n is equal to 0. In certain particular embodiments, X is an NR' group,with R' preferably being a methyl. In this embodiment, R is for example a (C1-C6)alkyl, in particular a methyl. According to a particular embodiment of the present invention, the compound of formula (I) is selected from the following list, in particular for use according to the invention:Compounds n R XH1 0 CH3 -H2 0 CH2CH3 -H3 0 (CH2)2CH3 -H4 0 (CH2)3CH3 -H5 0 (CH2)4CH3 -H6 0 (CH2)5CH3 -H7 0 (CH2)6CH3 -H8 0 (CH2)7CH3 -H9 0 (CH2)9CH3 -H10 0 (CH2)11CH3 -H11 0 Phenyl -H12 0 Ethylpentyl -H13 0 Furyl -H14 0 Isobutyl -H15 0 Propylene -H16 0 Chlorobenzyl -H17 0 CF3benzyl -H18 0 Cyclopropyl -H19 1 Methyl OH20 1 Ethyl OH21 1 Propyl OH22 1 Butyl OH23 1 Pentyl OH24 1 Hexyl OH25 1 Decyl OH26 1 Dodecyl OH27 1 Ethylhexyl OH28 1 CH2CH2OCH3 OH30 1 Phenyl OH31 1 C6H4-Cl OH32 1 (+) menthyl OH33 1 (-) menthyl OH34 1 Cholesteryl OH35 0 C6H4-Cl -H36 0 C6H4-CF3 -In a particular embodiment,the compound of formula (I) is selected from compounds of H1, H2, H3, H4, H5, H6, H7, H8, H9, H10 and / or of H19, H20, H21, H22, H23, H24, H26.According to a particular embodiment, in the compound of formula (I), n=0 and R is a methyl (H1) or a cyclopropyl (H18), or n=1, X=O and R is a hexyl (H24).Another subject of the present invention is a compound of the following formula (I):in which n, X and R are as defined above.According to a preferred embodiment, in the compound of formula (I), X is an oxygen atom. According to a particular embodiment, when X is an oxygen atom and n is equal to 1, the compound of formula (I) as defined above comprises an R other than a methyl, propyl, and heptyl group. When n=1 and X is an oxygen atom, R is preferably a hexyl. In a preferred embodiment, in the compound of formula (I), n is equal to 0 and R is a (C1-C4)alkyl, in particular a methyl,or a saturated or unsaturated, non-aromatic, hydrocarbon ring system, comprising in particular 3 members, in particular a cyclopropyl.Preferably, in the compound of formula (I), n is equal to 0 and R is a cyclopropyl.Cultivated plants and seedsSaid plants and crop weeks on which the compound of formula (I) is used are in particular chosen from the group consisting of cereals such as wheat, corn, barley, rice, soybeans, rapeseed, fruits and vegetables such as potatoes, carrots, apple trees, peach trees, apricot trees, 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, 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. Pathogens The phytopathogens against which the compound of formula (I) is used as an antifungal and / or antibacterial agent are as listed below. Fungi The said fungi pathogenic to plants and crop seeds are ascomycetes or basidiomycetes, preferably ascomycetes. Said pathogenic fungi of plants and crop seeds within the scope of the present invention are pathogenic fungi of plants and crop seeds which can be chosen from the genera: Fusarium, Botrytis, Alternaria, Erisyphe, Claviceps, Gaeumannomyces, Leptosphaeria, Microdochium, Mycosphaerella, Oculimacula, Blumeria, Pyrenophora, Ramularia, Rhynchosporium, Phakospora,Zymoseptoria, Puccinia, Rhizoctonia, Sclerotinia, Septoria, Bipolaris, Botryosphaeria, Botryosporium, Phoma, Sclerotium and Verticillium.The genus Fusarium includes the following species: Fusarium affine, Fusariumarthrosporioides, 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. tomato root, Fusarium oxysporum f.sp. spinacia, Fusariumoxysporum, Fusarium pallidoroseum, Fusarium patch, Fusarium proliferatum, Fusarium redolens, Fusarium sacchari, Fusarium solani, Fusarium subglutinans, Fusarium sulphureum, Fusarium tricinctum, Fusarium wilt.The genus Botrytis includes in particular the following species: Botrytis allii, Botrytis anthophila,Botrytis cinerea, Botrytis fabae, Botrytis narcissicola.The genus Alternaria includes in particular the following species: Alternaria alternata, Alternariabrassicae, 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.The genus Erisyphe includes in particular the following species: Erisyphe necator, Erysiphe betae, Erysiphe brunneopunctata, Erysiphe cichoracearum, Erysiphe cruciferarum, Erysiphe graminis f. sp. Avenae, Erysiphe graminis f.sp. tritici, Erysiphe heraclei, Erysiphe pisi.The genus Claviceps includes notably the following species: Claviceps fusiformis, Clavicepspurpurea, Claviceps sorghi, Claviceps zizaniae.The genus Gaeumannomyces includes notably the species Gaeumannomyces graminis.The genus Leptosphaeria includes notably the following species: Leptosphaeria nodorum, Leptosphaeria acuta, Leptosphaeria cannabina, Leptosphaeria coniothyrium, Leptosphaeria libanotis, Leptosphaeria lindquistii, Leptosphaeria maculans, Leptosphaeria musarum, Leptosphaeria pratensis, Leptosphaeria sacchari, Leptosphaeria woroninii.The genus Microdochium includes notably the following species: Microdochium spp.Microdochium bolleyi,Microdochium dimerum, Microdochium panattonianum, Microdochiumphragmitis, Microdochium oryzae.The genus Mycosphaerella includes the following species: Mycosphaerella arachidis,Mycosphaerella areola, Mycosphaerella berkeleyi, Mycosphaerella bolleana, Mycosphaerella brassicicola, Mycosphaerella caricae, Mycosphaerella caryigena, Mycosphaerella cerasella, Mycosphaerella coffeicola, Mycosphaerella confusa, Mycosphaerella cruenta, Mycosphaerelladendroides, 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 pistachina, Mycosphaerella platanifolia, Mycosphaerella polymorpha, Mycosphaerella apple, Mycosphaerella punctiformis,Mycosphaerella pyri. Le genre Oculimacula comprend nomentally les espèces Oculimacula acuformis et Oculimaculayallundae. Le genre Blumeria comprend nomentally l'espèce Blumeria graminis. Le genre Pyrenophora comprend nomentally les espèces suivantes: Pyrenophora avenae, Pyrenophorachaetomioides, Pyrenophora graminea, Pyrenophora seminiperda, Pyrenophora teres, Pyrenophora teres f. spotted, Pyrenophora teres f. teres, Pyrenophora tritici-repentis.The genus Ramularia includes the following species: Ramularia collo-cygni, Ramulariabeticola, Ramularia coryli, Ramularia cyclaminicola, Ramularia macrospora, Ramularia menthicola, Ramularia necator, Ramularia primulae, Ramularia spinaciae, Ramularia subtilis, Ramularia tenella, Ramularia vallisumbrosae.The genus Rhynchosporium includes the species Rhynchosporium secalis.The genus Phakospora includes the following species: Phakospora pachyrhizi, Phakopsoragossypii, 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 pisi, Colletotrichum sublineolum,Colletotrichum trichellum, Colletotrichum trifolii, Colletotrichum truncatum, Pythium spp.The genus Zymoseptoria includes in particular the species Zymoseptoria tritici.The genus Puccinia includes in particular the following families: Puccinia angustata, Pucciniaarachidis, 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.The genus Rhizoctonia includes in particular the following species: Rhizoctonia solani, Rhizoctoniaoryzae, Rhizoctonia cerealis, Rhizoctonia leguminicola, Rhizoctonia rubi.The genus Sclerotinia includes in particular the following species: Sclerotinia borealis, Sclerotiniabulborum, Sclerotinia minor, Sclerotinia ricini, Sclerotinia sclerotiorum, Sclerotinia spermophila, Sclerotinia trifoliorum. The genus Septoria comprises notably the following species: 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 pisi, Septoria rhododendri, Septoria secalis, Septoria selenophomoides.The genus Bipolaris includes the following species: Bipolaris cactivera, Bipolaris cookei,Bipolaris incurvata, Bipolaris sacchari.The genus Botryosphaeria includes the following species: Botryosphaeria cocogena,Botryosphaeria dothidea, Botryosphaeria marconii, Botryosphaeria obtusa, Botryosphaeria rhodina, Botryosphaeria ribis, Botryosphaeria stevensii.The genus Botryosporium includes the following species: Botryosporium beautiful. Le genre Phoma comprend notably les species suivantes : Phoma clematidina, Phomacostaricensis, 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.The genus Sclerotium includes in particular the species Sclerotium cinnamomi and Sclerotium delphinii.The genus Verticillium includes in particular the following species: Verticillium albo-atrum,Verticillium alfalfae, Verticillium dahliae, Verticillium isaacii, Verticillium klebahnii, Verticillium longisporum, Verticillium nonalfalfae, Verticillium theobromae, Verticillium wilt, Verticillium zaregamsianum. Selon un mode de réalisation de l'invention, lesdits champignons et / ou oomycètes pathogens desplantes et semences de culture dans le cadre de la présente invention sont des champignons pathogenesdes plants et semences de culture des genres Zymoseptoria, Fusarium, Sclerotinia, Botrytis,Alternaria, in particular selected from the group consisting of Zymoseptoria tritici, Fusarium oxysporum, Fusarium solani, Fusarium avenaceum, Fusarium culmorum, Fusarium graminearum, Fusarium moniliforme, Fusarium poae, Fusarium proliferatum, Fusarium sporotrichioides, Fusarium subglutinans, Fusarium tricinctum, Sclerotinia borealis, Sclerotinia bulborum, Sclerotinia minor, Sclerotinia ricini, Sclerotiniasclerotiorum, Sclerotinia spermophila, Sclerotinia trifoliorum, Botrytis allii, Botrytis anthophila, Botrytis cinerea, Botrytis fabae, Botrytis narcissicola, Alternia alternata, Alternaria solani and Alternaria brassisicola, preferably selected from the group Zymoseptoria tritici, Fusarium solani, Sclerotinia sclerotiorum, Botrytis cinerea and Alternaria alternata. According to one embodiment of the invention,said fungi and / or oomycetes pathogenic to plants and crop seeds in the context of the present invention are advantageously fungi pathogenic to plants and crop seeds of the genera Zymoseptoria, Fusarium, Sclerotinia, Botrytis, and Alternaria, in particular the strains Zymoseptoria tritici, Fusarium solani, Fusarium graminearum, Sclerotinia sclerotiorum, Botrytis cinerea, and Alternaria alternata. According to a particular embodiment, the invention relates to the use of the compound of formula (I) as described above for its antifungal activity on fungi and / or oomycetes pathogenic to plants and crop seeds chosen from the group Zymoseptoria tritici, Fusarium solani, Sclerotinia sclerotiorum, Botrytis cinerea and Alternaria alternata, in particular Zymoseptoria tritici and Fusarium solani, in particular Zymoseptoria tritici. In this embodiment, R preferably represents a (C1-C20)alkyl, preferably (C1-C15)alkyl,even more preferably (C1-C12) alkyl, and in particular a methyl, pentyl or hexyl, a cycloalkyl such as cyclopropyl, or an aryl-(C1-C6)alkyl group optionally substituted by a halogen atom, in particular a chlorobenzyl, and n is equal to 0 or 1. According to a variant, one or more methylene groups of the group R, when the latter is an alkyl, are optionally replaced by an oxygen atom.According to a particular embodiment, the invention relates to the use of a compound of formula (I) comprising a group R which may be a pentyl or hexyl, preferably a pentyl, with n equal to 0, for its antifungal and / or antibacterial activity on fungi and / or oomycetes and / or pathogenic bacteria of plants and crop seeds, preferably on Zymoseptoria tritici, Fusarium solani, Sclerotinia sclerotiorum, Botrytis cinerea or Alternaria alternata, in particular on Zymoseptoria tritici or Fusarium solani,in particular Zymoseptoria tritici.According to a preferred embodiment, the invention relates to the use of a compound of formula (I) comprising a group R which may be a methyl or hexyl, preferably a methyl with n equal to 0 or a hexyl with n = 1 and X = an oxygen atom, for its antifungal and / or antibacterial activity on fungi and / or oomycetes and / or pathogenic bacteria of plants and crop seeds, preferably on Zymoseptoria tritici, Fusarium solani, Sclerotinia sclerotiorum, Botrytis cinerea or Alternaria alternata, in particular on Zymoseptoria tritici or Fusarium solani, in particular Zymoseptoria tritici.According to another preferred embodiment, the invention relates to the use of a compound of formula (I) comprising a group R which may be a cyclopropyl, n equal to 0, for its antifungal activity and / or antibacterial on fungi and / or oomycetes and / or pathogenic bacteria of plants and crop seeds,preferably on Zymoseptoria tritici, Fusarium solani, Sclerotinia sclerotiorum, Botrytis cinerea or Alternaria alternata, in particular on Zymoseptoria tritici or Fusarium solani, in particular Zymoseptoria tritici. Bacteria The pathogenic bacteria of plants and crop seeds in the context of the invention may be Gram-positive or Gram-negative bacteria, preferably of the genera Erwinia, Pseudomonas, Ralstonia, Agrobacterium, Xanthomonas, Xylella, Dickeya, Pectobacterium, Clavibacter, and Candidatus. In some embodiments, the phytopathogenic bacteria within the scope of the invention do not include Pseudomonas aeruginosa bacteria. By "Gram-positive" or "Gram +" bacteria is meant a bacterium that has a single-membrane structure surrounded by a thick wall predominantly composed of peptidoglycan and that appears mauve by the Gram staining technique. By "Gram-negative" or "Gram -" bacteria is meant,a bacterium that has a unimembrane structure surrounded by a wall consisting of a thin layer of peptidoglycan and a phospholipid bilayer including lipopolysaccharide and which appears pink by the Gram stain technique. According to one embodiment of the invention, said pathogenic bacteria of plants and crop seeds are pathogenic bacteria of plants and crop seeds of the genera Erwinia, Pseudomonas, Ralstonia, Agrobacterium, Xanthomonas, Xylella, Dickeya, Pectobacterium, Clavibacter, and Candidatus, in particular chosen from the group consisting of Erwiniapersicina, Erwinia amylovora, Pseudomonas syringae, Ralstonia solanacearum, Agrobacteriumtumefaciens, Xanthomonas oryzae, Xanthomonas campestris, Xanthomonas axonopodis, Xylellafastidiosa, Dickeya dadantii, Dickeya solani, Pectobacterium carotovorum, Pectobacteriumatrosepticum, Clavibacter michiganensis, Clavibacter sepedonicus, and Candidatus Liberibacter,in particular Erwinia persicina, Pseudomonas syringae and Dickeya dadantii.According to one embodiment of the invention, said pathogenic bacteria of plants and crop seeds in the context of the present invention are advantageously pathogenic bacteria of plants and crop seeds of the genera Erwinia, Pseudomonas and Dickeya, in particular the strains Erwiniapersicina, Pseudomonas syringae and Dickeya dadantii.According to a particular embodiment of the invention, the compound of formula (I) as described above, preferably comprising R which may be a furyl, with n being equal to 0, is used for its antibacterial activity on pathogenic bacteria of plants and crop seeds, preferably chosen from the group consisting of Erwinia persicina, Erwinia amylovora, Pseudomonas syringae, Ralstoniasolanacearum, Agrobacterium tumefaciens, Xanthomonas oryzae, Xanthomonascampestris, Xanthomonas axonopodis, Xylella fastidiosa, Dickeya dadantii, Dickeya solani,Pectobacterium carotovorum, Pectobacterium atrosepticum, Clavibacter michiganensis, Clavibactersepedonicus, and Candidatus Liberibacter, in particular Erwinia persicina, Pseudomonas syringae and Dickeya dadantii. More preferably, these are bacteria of the genus Erwinia such as E. persicina, E. chrysanthemi or E. amylovora. According to a particular embodiment of the invention, the compound of formula (I) as described above, preferably comprising R which may be a (C1-C20)alkyl, preferably (C1-C12)alkyl, and in particular a methyl, ethyl, pentyl or decyl, or an aryl group optionally substituted by a halogen atom, in particular a chlorobenzyl, and n is equal to 0 or 1, is used for its antibacterial activity on pathogenic bacteria of plants and crop seeds, preferably chosen from the group consisting of Erwinia persicina, Erwinia amylovora, Pseudomonas syringae, Ralstoniasolanacearum, Agrobacterium tumefaciens, Xanthomonas oryzae,Xanthomonascampestris, Xanthomonas axonopodis, Xylella fastidiosa, Dickeya dadantii, Dickeya solani, Pectobacterium carotovorum, Pectobacterium atrosepticum, Clavibacter michiganensis, Clavibactersepedonicus, and Candidatus Liberibacter, in particular Erwinia persicina, Erwinia chrysantemi, Pseudomonas syringae and Dickeya dadantii. Preferably, in this embodiment, when n=1 and X is an oxygen atom, R is not an alkyl comprising more than 6 carbon atoms, nor an aryl. Process for preparing the compound according to the inventionAccording to a particular embodiment of the present invention, the compound of formula (I) according to the invention is capable of being obtained by a synthesis route A or B as described in the examples below. Control method according to the invention The invention also relates to a method for controlling fungi and / or oomycetes and / or pathogenic bacteria in plants and crop seeds,comprising a step of applying a compound of formula (I) according to the invention comprising an n equal to 0 or 1.The method for combating fungi, oomycetes and / or pathogenic bacteria in plants and crop seeds according to the present invention comprises the following steps:(a) Mixing one or more compound(s) of formula (I) as defined above, with n being equal to 0 or 1, in a solvent, preferably aqueous based, which may contain additives such as alcohols or compatibilizers such as DMSO and / or surfactants;(b) Applying this mixture to the crop plants and / or coating said seeds with this mixture. According to a particular embodiment of the invention, the compatible solvent of step (a) is chosen from alcohols or compatibilizers such as DMSO. Advantageously, step (a) consists of mixing one or more compound(s) of formula (I) as described according to any one embodiment above,with n being equal to 0 or 1, in a compatible solvent, preferably aqueous based, which may contain additives such as alcohols or compatibilizers such as DMSO and / or surfactants adapted according to the particular physicochemical properties of the active ingredient in question, typically chosen from polyoxyethylene sorbitan monolaurate (such as Tween20® or Tween®80) or alkyl-glycopyranosides, typically C8-C10 alkyl-glycopyranosides, (such as Cantor®), all in proportions allowing the application and maintenance of the intended activity. In one embodiment, the solvent comprises water, from more than 0% to 5% v / v of at least one additive such as at least one alcohol or such as at least one compatibilizer, in particular DMSO, and / or from more than 0% to 10% v / v of at least one surfactant, typically as defined above,the percentages being expressed by volume relative to the total volume of the mixture of step (a). According to a particular embodiment of the invention, in step (a) of the method described above, the additives are chosen from alcohols, such as ethanol, propanol, DMSO or additives known to those skilled in the art. According to a particular embodiment of the invention, the method for combating fungi, oomycetes and / or pathogenic bacteria of plants and crop seeds comprises an additional optional step (a') after step (a). The additional optional step (a') may be sonication or passage through a high-velocity mixer (vortex) of the mixture obtained in step (a). The method for combating fungi and / or oomycetes and / or pathogenic bacteria of plants and crop seeds according to the invention,comprises the application of the mixture of one or more compounds of formula (I) at a dose ranging from 500 mg / L to 1 g / L for a treated surface ranging from 0.5 to 5 m, 2. The method for combating fungi and / or oomycetes and / or pathogenic bacteria in plants and crop seeds according to the invention comprises applying the mixture of one or more compounds of formula (I) at a frequency of 1 to 3 times per week. The method for combating fungi and / or oomycetes and / or pathogenic bacteria in plants and crop seeds according to the invention comprises applying the mixture of one or more compounds of formula (I) to an area of between 0.00001 and 10 hectares, in particular between 0.00001 and 1 hectare, preferably 0.00001 and 1000 m2. According to a particular embodiment of the invention, the method for combating fungi and / or oomycetes and / or pathogenic bacteria in plants and crop seeds is curative or preventive.The control method according to the invention targets in particular the following fungi: Zymoseptoria tritici, Fusarium solani, Fusarium graminearum, Sclerotinia sclerotiorum, Botrytis cinerea, and Alternariaalternata. The control method according to the invention targets in particular the following bacteria: Erwinia persicina, Pseudomonas syringae and Dickeya dadantii. Composition according to the invention The invention also relates to a composition for combating fungi and / or oomycetes and / or pathogenic bacteria in plants and crop seeds comprising one or more compounds of formula (I) as described above with n being equal to 0 or 1, and at least one acceptable excipient. According to a particular embodiment, the composition according to the invention comprises an amount of compound(s) of formula (I) of between 500 and 1000 mg / mL, preferably 600 and 1000 mg / mL, even more preferably 800 and 1000 mg / mL.According to one embodiment of the invention, said at least one acceptable excipient of the composition may be chosen from surfactant compounds, or surfactants, known to those skilled in the art, in particular non-ionic (neutral) surfactants or surfactants such as polyoxyethylene sorbitan monolaurate, such as Tween® or alkyl-glycopyranosides, typically (C8-C10)alkyl-glycopyranosides, such as decyl octyl glycopyranosides of D-glucopyranose or its oligomers (CAS No. 6815-73-1), such as for example Cantor®. According to a particular embodiment of the invention, the composition may further comprise at least one other antifungal compound, preferably chosen from the group consisting of triazoles such as mefentrifluconazole, prothioconazole, metconazole for example; strobilurins such as lebixafen, fluxapyroxad, benzovindiflupyr, fluopyram, penthiopyrad or boscalid; despicolinamides or multisite compounds.In one embodiment, said at least one other antifungal compound is chosen from the group consisting of triazoles, strobilurins, boscalid, picolinamides, as presented as examples above. According to a particular embodiment, the composition according to the invention is liquid, preferably aqueous. EXAMPLES The compounds illustrated in the examples below were used according to one of the following synthesis routes:Synthesis route A: According to one embodiment of the invention, a mass of hinokitiol is dissolved in 1 to 10 mL, preferably 3 to 7 mL, even more preferably in 6 mL of anhydrous acetone, to which triethylamine (1 molar equivalent) is added at room temperature (25°C). The solution is placed under magnetic stirring and cooled to a temperature between 0 and 15°C, preferably to 5°C by an ice bath.Alkyl or aryl chloride or chloroformate (1 molar equivalent) is dissolved in 1 to 10 mL, preferably in 4 mL of anhydrous acetone, and then added dropwise using a dropping funnel, until a white precipitate (corresponding to triethylammonium) appears. After the addition, the ice bath is removed and the reaction continues at room temperature until completion. The precipitate is removed by filtration and the solvent is then evaporated. The crude reaction product is then dissolved, then washed and the organic phase is then dried and concentrated under reduced pressure. The residue is then purified by flash chromatography. The mass of dissolved hinokitiol is between 0.01 and 5 g, in particular between 0.5 and 3 g. Preferably, the mass of hinokitiol used in this synthesis route is 1 g.According to a particular embodiment of the invention, after 24 hours of reaction, an optional step can be carried out with the addition of one molar equivalent of pyridine and one molar equivalent of alkyl chloride. Synthesis route B: According to one embodiment of the invention, a mass of hinokitiol is dissolved in 0.5 to 10 mL, preferably in 1 to 5 mL, even more preferably in 2 mL of anhydrous pyridine (8 molar equivalents) at room temperature. The solution is cooled to a temperature between 0 and 15°C, preferably to 5°C by an ice bath. With stirring, the alkyl or aryl chloroformate (1 molar equivalent) is added dropwise using a micropipette, until the appearance of a white precipitate corresponding to pyridinium chloride. At the end of the addition, the reaction is continued at room temperature.Thin layer chromatography (TLC) monitoring is carried out to determine the end of the reaction (absence of evolution or total disappearance of the reagent). The reaction crude is then treated by adding 25 mL of iced distilled water to solubilize the precipitate formed. The aqueous phase is extracted with diethyl ether (2x25 mL). The organic phase is then dried over MgSO4 and then concentrated under reduced pressure. The residue is purified by flash chromatography (eluent n-heptane / ethyl acetate). The mass of dissolved hinokitiol is between 0.01 and 5 g, in particular between 0.05 and 3 g. Preferably, the mass of hinokitiol used in this synthesis route is 0.5 g. According to a particular embodiment, synthesis route B of the compound according to formula (I) is carried out with two molar equivalents of pyridine and two molar equivalents of alkyl chloride.Example 1: In vitro study of compounds according to the invention on fungiCompounds H1 to H18 below were obtained by reaction of an equimolar mixture of hinokitiol, acyl chloride and triethylamine. Compounds H19 to H34 were obtained in a similar manner, by semisynthesis from hinokitiol by replacing the ester function with the carbonate group.Table 1. Minimum inhibitory concentrations (MIC) for the compounds studied on different pathogens Sclerotinia AlternariaBotrytis cinerea Fusarium solanZymoseptoria Compounds sclerotiorum alternata. i tritici CMI 50 CMI 100 CMI 50 CMI 100 CMI 50 CMI 100 CMI 50 CMI 100 CMI 50 CMI 100Hinokitiol <1.56 3.13 6.25 6.25 <1.56 <1.56 6.25 6.25 <1.56 3.13H1 <1.56 <1.56 6.25 6.25 1.56 3.13 3.13 12.5 <1.56 3.13H2 <1.56 3.13 6.25 12.5 <1.56 <1.56 3.13 12.5 <1.56 3.13H3 <1.56 3.13 6.25 12.5 1.56 3.13 3.13 12.5 <1.56 3.13H4 <1.56 <1.56 12.5 12.5 1.56 3.13 6.25 12.5 3.13 3.13H5 <3.13 3.13 6.25 12.5 <3.13 3.13 3.13 12.5 3.13 3.13H6 <1.56 <1.56 12.5 12.5 <3.13 3.13 3.13 12.5 3.13 3.13H7 3.13 6.25 12.5 12.5 <3.13 3.13 3.13 12.5 3.13 3.13H8 3.13 6.25 12.5 12.5 1.56 3.13 6.25 25 3.13 3.13H9 1.56 3.13 12.5 25 3.13 6.25 3.13 25 3.13 6.25H10 3.13 3.13 12.5 25 12.5 12.5 12.5 >100 6.25 6.25H11 6.25 12.5 12.5 25 3.13 12.5 1.56 12.5 3.13 6.25H12 25 25 25 >100 12.5 25 12.5 >100 25 50H13 3.13 6.25 12.5 12.5 3.13 3.13 3.13 25 3.13 3.13H14 3.13 6.25 6.25 6.25 6.25 25 3.13 50 3.13 6.25H15 12.5 50 6.25 6.25 6.25 12.5 3.13 100 3.13 6.25H16 12.5 12.5 6.25 12.5 6.25 12.5 3.13 25 3.13 6.25H17 6.25 6.25 12.5 12.5 3.13 3.13 1.56 12.5 3.13 6.25H18 1.56 3.13 6.25 12.5 1.56 6.25 6.25 25 1.56 3.13H19 1,56 1.56 12.5 12.5 6.25 6.25 25 >100 3.13 6.25H20 1.56 3.13 12.5 12.5 6.25 12.5 12.5 >100 3.13 6.25H21 3.13 6.25 12.5 25 6.25 6.25 25 100 1.56 3.13H22 3.13 3.13 6.25 12.5 1.56 12.5 6.25 100 3.13 3.13H23 3.13 6.25 12.5 12.5 3.13 12.5 6.25 100 6.25 6.25H24 1.56 3.13 12.5 12.5 3.13 6.25 3.13 25 3.13 6.25H25 1.56 3.13 50 100 12.5 25 6.25 >100 12.5 12.5H26 3.13 6.25 100 >100 50 100 50 >100 6.25 25H27 25 25 >100 >100 50 50 50 >100 >100 >100H28 6.25 12.5 12.5 50 12.5 12.5 12.5 100 6.25 12.5:31 ND ND 6.25 6.25 1.56 1.56 6.25 25 3.13 3.13Tebuconazole <0.78 <0.78 50 >50 3.13 6.25 25 >50 1.56 1.56Bixafen <0.78 <0.78 1.56 3.13 1.56 3.13 >50 >50 0.78 1.56Results:Compounds H1 - H18, H19 - H31 are active against all pathogens tested (Table 1). Simple modifications to the hinokitiol compound therefore allow for in vitro activity to be maintained.In particular, compounds with a linear hydrocarbon chain,either H1-H10 and H19-H25 are the most active.Example 2: In vitro study on non-multiresistant and multiresistant susceptible strains of Zymoseptoria triticiMaterials and methods:A sample of wheat leaves showing symptoms of septoria was taken from an untreated wheat field (with antifungals). 8 monospore strains of Zymoseptoria tritici were obtained from the infected leaves, using the protocol described by Siah et al. (Azoxystrobinresistance of French Mycosphaerella graminicola strains assessed by four in vitro bioassays and byscreening of G143A substitution, Crop Protection, 2010, 29 (7), 737–743). The isolated strain of Zymoseptoria tritici, named T02596, was also included in the work of this study. The 9 strains were grown on Potatoes Dextrose Agar (PDA) medium.Sigma Aldrich) at 39 g / L for 6 days to produce the inoculum necessary for subsequent analyses. The strains were then analyzed by determining the median inhibitory concentrations (IC50) and minimum inhibitory concentrations (MIC) (Table 2). The compounds analyzed are hinokitiol (H0) and compound H5 bearing an alkyl chain comprising five carbons (pentyl). Table 2. Median inhibitory concentrations (IC, 50 ) and minimum inhibitory concentrations (MIC) of Bixafen, Tebuconazole and compounds H0 and H5 for different strains. Results: It is observed that hinokitiol is significantly less effective against all 9 strains studied, whether sensitive or resistant to conventional antifungals with an IC50 of approximately 14 mg / L. In comparison, compound H5 shows equivalent or significantly higher fungal activity against the various lineages of the pathogen with an IC 50average of 7.2 mg / L. For example, compound H5 is more active than the two reference antifungal agents against resistant strains #187 and #204 with CIs 50respectively 6.8 and 11.6 mg / L compared to 25 mg / L for Bixafen and Tebuconazole. This illustrates the interest of the chemical modification carried out according to the invention.Example 3: In planta evaluation on wheat plants under infection conditionsThis test was carried out on wheat plants, grown in a greenhouse and infested with the fungus Zymoseptoria tritici.Plants, grown from sowing seeds of the Alixan variety (Limagrain), are grown in plastic horticultural pots containing universal potting soil (Gamm Vert® brand) inside a greenhouse under semi-controlled temperature and light conditions: 18 ± 2°C with a day / night cycle of 16⁄8 hours. The pots are watered every three days. Wheat grains are first placed on damp paper in Petri dishes (12 x 12 cm) and stored in the dark at a temperature of 20°C for 24 hours, then 4°C for 48 hours and again 20°C for 24 hours.The germinated seeds are then sown in the pots: replicas of four pots containing twelve seeds each are prepared for each molecule tested. When the wheat reaches the three-leaf stage, 21 days post-sowing, 120 milliliters of aqueous solutions of the compounds dissolved in 0.5% of the final volume of DMSO are applied simultaneously to the four pots of each modality with a hand-held sprayer on the leaves using an adjuvant: 0.05% (v / v) of polyoxyethylene sorbitan monolaurate (Tween 20, Sigma Aldrich) or 0.15% of ethoxylated triglyceride 10 EO (Cantor® Grandes Cultures, Jouffray Drillaud). The plants grown as a control are sprayed with the same volume of water, DMSO and adjuvant.Two days after treatment, the plants are inoculated in the same way as the treatment with 120 milliliters of spore suspension of strain T02596, produced by subculture in Petri dishes containing PDA (Potato Dextrose Agar) six days before use, at a concentration of 106 spores per milliliter with 0.05% (v / v) Tween 20 or 0.15% (v / v) Cantor®. The plants are covered with a transparent polyethylene bag for three days to ensure a favorable humidity level for spore germination. Four days after inoculation, observation of spore germination on the adaxial surface of the leaves (upper surface) is carried out using a fluorescent marker, calcofluor, which reveals the fungus by fixation of chitin, the major compound of fungal cell walls.Three-centimeter fragments of the third leaf are cut (one leaf per pot, or four leaves per modality) and immersed for five minutes in a 0.1% (w / v) solution of calcofluor (Fluorescence Brightener 28, Sigma) dissolved in a 0.1 M TRIS-HCl buffer (Trizma® HCl) and whose pH is adjusted to 8.5 by adding aqueous NaOH solution. The fragments are then rinsed by immersing them for two minutes in reverse osmosis water and then rinsed again in another beaker of reverse osmosis water before being dried on a sheet of absorbent paper and then placed on a glass slide and covered with a coverslip. Observations are carried out by fluorescence microscopy (Nikon Eclipse 80i). Photographs are taken using a camera (Digitalcamera, DXM1200C) and image capture software (NIS elements BR).The protective effect of the compounds is evaluated 21 days post-inoculation by comparison with the control plants and by visual quantification of the percentage of necrotic leaf surface and rating of asporulation, i.e. the density of pycnidia, on this involved surface (rating from 0 for the lowest density to 5 for the highest density). The activity of hinokitiol and compounds H5 and H6 according to the invention was evaluated in comparison with a control represented by the plants treated only with water and an adjuvant, namely 1000 mg / L of Tween 20 (or polyoxyethylene sorbitan monolaurate) at 0.005% by volume. Table 3. Results obtained for the control, and for compounds H0, H5 and H6. Results: The compounds significantly inhibit the growth of Zymoseptoria tritici and necrosis of wheat leaves under controlled greenhouse contamination conditions. The results illustrate a reduction in infection during foliar spray treatment with hinokitiol or the compounds according to the invention (Table 3). Indeed, approximately 80% of the surface of the treated leaves is not affected by the symptoms of necrosis caused by Zymoseptoria tritici compared to untreated contaminated plants and the density of pycnidia is lower. Example 5: Evaluation of the antibacterial effect of the compounds according to the invention The compounds of formula (I) according to the invention H5 and H13 as well as hinokitiol were tested on the bacterium Erwinia persicina. The minimum inhibitory concentration was measured, for inhibitions greater than or equal to 95% (Table 4). Table 4. Minimum inhibitory concentrations for compounds H0 (hinokitiol), H5 and H13.Erwinia persicina Bacillus Gram - H. inokitiol 6,25 H5 3,13 H13 6,25Results: Compounds H5 and H13 according to the invention exhibit superior antibacterial activity to that of hinokitiol. Example 6: In planta efficacy of compounds according to the invention on the wheat-Zymoseptoria tritici pathosystem. Compounds of formula (I) according to the invention H1, H18 and H24 were tested on wheat against septoria blight caused by the hemibiotrophic phytopathogenic agent Zymoseptoria tritici, to evaluate their protective efficacy in greenhouses (semi-controlled conditions). The antifungal effect of these compounds on the epiphytic growth of the fungus was also measured by staining and microscopic observations. For this example, compounds H1, H18 and H24 correspond respectively to compounds A1, A18 and A11. Materials and methods Tested modalities The tested modalities are presented in Table 5. Table 5. Modalities tested during greenhouse protection tests (in planta).In planta concentration Untreated and uninoculated control Untreated and inoculated control A1 1 g / L + 0.01% Tween 20 A11 1 g / L + 0.01% Tween 20 A18 1 g / L + 0.01% Tween 20 Greenhouse protection test The protection test is carried out in a greenhouse at 18°C (± 2°C) with a 16h / 8h photoperiod, on whole wheat plants and under artificial contamination with the monospore strain of Z. tritici T02596 (virulent strain isolated in 2014 in Hauts-de-France). For the repetitions, 36 plants (3 pots of 12 plants) are used per modality. Two controls are used in the test: an untreated and uninoculated control and an untreated and inoculated control. The experimental protocol consists of: ^Sowing wheat in a greenhouse (36 plants per modality).^ Treating the plants with the products at the 4th emerging leaf stage.^ Contaminating the plants with a suspension of Z. tritici spores (106 spores / mL) 48 hours after treatment.The spore suspension is obtained from in vitro fungal cultures previously incubated for 8 days. ^Cover the pots with transparent polyethylene bags for 3 days to maintain the relative humidity close to 100% (required for infection). ^Remove the bags after 3 days post-inoculation.^ Score the infected leaves 3 weeks after inoculation by measuring: o The percentage of diseased leaf area (3rd leaf) with septoria-like symptoms (necrosis). o The level of sporulation (pycnidia density score, from 0 to 5) on the symptoms noted. The scores correspond to: 0: no pycnidia on the symptoms. 1: between 0 and 20% of the symptoms contain pycnidia. 2: between 20 and 40% of the symptoms contain pycnidia. 3: Between 40 and 60% of symptoms contain pycnidia. 4: Between 60 and 80% of symptoms contain pycnidia. 5: Between 80 and 100% of symptoms contain pycnidia.In planta antifungal testThe in planta antifungal activity of the three compounds was evaluated by determining the effect of the treatments on the epiphytic growth of the fungus (on the surface of wheat leaves) 5 days after inoculation. The treatment and inoculation conditions of the plants were identical to those used for the protection tests above. The revelation of the fungus was carried out using the fluorescent marker Calcofluor, by immersing the leaf fragments for 5 min in a 0.1% (w / v) solution of Calcofluor (Brightener 28, Sigma) previously solubilized in a 0.1 M Tris-HCl buffer (pH 8.5). This fluorescent marker reveals the fungus by fixation to chitin, the major component of fungal cell walls. The leaves are then rinsed for 2 min in distilled water. After drying in the dark, the leaves are placed between slides and coverslips, then observed under UV with an epifluorescence microscope (Nikon, eclipse 80i).Six leaf fragments from different pots were used for each modality. Results Protection efficacy in greenhouse The contaminations took place under good conditions and allowed good expression of the disease, both in terms of symptoms and sporulation (production of pycnidia). The average in control plants (untreated and inoculated) was 51.7% for the diseased leaf area (Figure 1A) and 2.94% for the level of sporulation (pycnidia density) (Figure 1B). Treatment with the molecules markedly reduced the level of disease and the level of sporulation on wheat plants, with average diseased leaf area of 12.4%, 9.7% and 15.1% in plants treated with compounds A1, A11 and A18, respectively (Figure 1A). Regarding sporulation, treatment with the molecules allowed the formation of pycnidia to be completely inhibited (Figure 1B).Furthermore, the protection results can also be viewed in the table below (Table 6) showing the effectiveness of the tested compounds on symptoms (necrosis and chlorosis) and sporulation (pycnidia density). Table 6. Percentage reduction of symptoms and sporulation compared to the untreated (NT) and inoculated control. Compound % reduction in symptoms % reduction in sporulation compared to the inoculated NT control compared to the inoculated NT control A. 1 - 76 % - 100 %A11 - 81% - 100%A18 - 71% - 100%In planta antifungal activity Monitoring of fungal growth in planta, by Calcofluor staining and fluorescence microscope observations, on wheat leaves 5 days after inoculation, showed that treatment with the compounds strongly reduced the epiphytic growth (on the leaf surface) of the fungus (Figures 2 and 3). The spores germinated normally and formed a fairly dense mycelial network on the leaf surface of the control plants, in order to penetrate the plant, while mycelial growth remained very limited on the leaves of the treated plants. These results confirm in planta the antifungal effect of compounds A1, A11 and A18 against Z. tritici, the agent responsible for wheat septoria. This antifungal activity therefore explains the reduction in disease severity observed visually.Conclusion The results show that the three compounds confer a significant reduction in disease severity (necrosis and chlorosis) and sporulation (pycnidia density), with protection levels (disease reduction) of 76%, 81% and 71% for molecules A1 (H1), A11 (H24) and A18 (H18), respectively. Furthermore, all three molecules completely inhibited the formation of pycnidia, which is beneficial for reducing the spread of the disease under field conditions. Finally, microscopic observations revealed that this protection against Z. tritici is due to a direct antifungal effect in planta against the phytopathogenic fungus on the leaf surfaces of the plant. Example 7: Efficacy of the compounds according to the invention on the germination of Fusarium solani Compounds H1 to H36 of formula (I) according to the invention were tested, in vitro, on the spores of the fungus F. solani.The objective is to evaluate the inhibitory efficacy of different compounds against the germination of F. solani spores. For this, the F. solani fungus was first cultivated on a Petri dish with PDA medium for a minimum of two weeks so that the strain produces spores. Subsequently, to recover the spores, under PSM a small amount of sterile water + Tween 80 solution was poured to facilitate their detachment, then this solution containing the spores was transferred into a 15mL Falcon tube. To estimate the spore concentration, a Malassez cell allows the spores to be counted under a microscope using this calculation:. Knowing that for the Malassez cell used: oQM: Total grid surface = 5mm2o RM: Surface of a rectangle = 1 / 20 mm2o eM: Elementary surface = 1 / 400 mm2o Depth = 0.2 ± 0.02 mmCalculation of the volume corresponding to 1 rectangle RM: = 0,01 ^^^o Knowing that 1mm3 = 10-3 ml, we convert to ml:^ = 0.01 × 10^^ = ^^^^ ^^ ^^ The final concentration in this case is approximately 2.17 x 10 7 spores / mL. Then, a 10 4spores per mL was prepared in MM1 + Glc medium at 5g / L by diluting the starting solution. Then 100µL of this solution was transferred into the corresponding wells on the plate according to this plan: 28 compounds were tested divided into 3 series. The first series includes the following compounds: H31, H3, H28, H9, H18, H7, H8 and H20. The second series consists of compounds H5, H14, H27, H35, H30, H22, H11, H12, H32 / 33, H15 and H21. The third series includes compounds H1, H10, H13, H24, H25, H2, H6, H26 and H36. The plates were then incubated at 22°C alternating between 12h day and 12h night with shaking at 190 rpm and an OD measurement was performed daily. The results presented here are retained during the exponential growth phase. The results show highly variable performances from one compound to another. For the compounds in the first series (Figure 4), the measurement retained is at D3 because the exponential phase is reached at that time.Compounds that achieve more than 90% inhibition with a negligible standard deviation stand out for their inhibitory efficacy. These are compounds H31, H28, H9, H18, H7, H8 and H20. For compounds in the second series (Figure 5), the measurement is retained at D5 because this corresponds to the exponential phase. Compounds with strong inhibitory activity (inhibition rates greater than 90%) are compounds H5, H14, H35, H11, H12 and H21. For compounds in the third series (Figure 6), the measurement is retained at D6 because this corresponds to the exponential phase. The compounds showing strong inhibitory activity (inhibition rates above 90%) are compounds H1, H10, H13, H2, H6 and H36.ConclusionThese results demonstrate the efficacy of the compounds tested against Fusarium solani.The compounds of the invention show a strong capacity to inhibit spore growth.In particular, compounds H28, H18 and H7 (Figure 4), H35 (Figure 5) and compounds H2 and H36 (Figure 6) stand out in this study, showing almost total efficacy. This could be explained by their ability to directly alter cell membranes or to interfere with metabolic processes critical for spore survival.Example 8: Screening test of the compounds according to the invention on the pathogens Erwinia persicina, Dickeya dadantii, Pseudomonas syringae Materials and methodsCompounds H1 to H36 according to the invention are studied. Each compound is tested at a concentration of 50 mg / L per well and each test is carried out in triplicate. One well contains 200 µL in total. The tests were carried out in triplicate in 96-well plates with a transparent flat bottom.100 µL of bacterial suspension from a culture inoculated with a 24-hour-old colony on TSA and grown overnight at 30°C in a mineral medium containing a glucose source was added per well with 2 µL of a 5 mg / mL solution of the test compound in DMSO and the volume was made up to 200 µL with the mineral medium. Bacterial growth was monitored by measuring absorbance at 600 nm at T0 and after 24 h and inhibition was calculated as follows:. Where ODvar test is the difference in optical density between the highest and lowest points of the bacterial growth curve for a test. ODvar control is the difference in optical density between the highest and lowest points of the bacterial growth curve in the control without antimicrobial compound. ResultsThe results of the tests on Erwinia persicina bacteria are shown in Figure 7. Most of the compounds tested show significant inhibitory power against Erwinia persicina, with compounds H31, H3, H9, H5, H1, H10, H13 and H2 in particular showing an inhibition rate greater than 80%.The results of the tests on Erwinia chrysanthemi bacteria are shown in Figure 8.Most of the compounds tested showed significant inhibitory activity against the Erwinia chrysanthemi strain, with compounds H31 and H5 in particular showing an inhibition rate of over 80% and compounds H3, H28, H9, H18, H7, H8, H11, H1, H2 and H6 showing an inhibition rate of over 90%. The results of the tests on Pseudomonas syringae bacteria are illustrated in Figure 9. Most of the compounds tested showed significant inhibitory activity against the Pseudomonas syringae strain, with compounds H20, H15 and H21 in particular showing an inhibition rate of over 80% and compounds H31, H28, H9, H18, H7, H8, H5, H14, H22, H11, H12, H1, H10, H13, H2 and H36 which have an inhibition rate greater than 90%.ConclusionAlthough the extent of the inhibitory effect of the compound may vary depending on the strain studied, it is observed that the compounds according to the invention make it possible to obtain significant inhibition on the different bacteria considered. In addition, some compounds exhibit a strong inhibitory effect for all the bacteria studied, in particular compounds H31, H9, H5, H1 and H2.
Claims
CLAIMS 1. Use of a compound of the following formula (I): in which- R representso a (C1-C20)alkyl, a heteroalkyl, a (C1-C20)alkenyl, a (C1-C20)alkynyl, said alkyl, heteroalkyl, alkenyl or alkynyl being optionally substituted by one or more substituents chosen from a halogen atom, an oxo group, a (C1-C8)alkyl, an OH group, a (C1-C6)alkoxy and a (C1-C6)haloalkyl, ora saturated or unsaturated and non-aromatic hydrocarbon-based cyclic or polycyclic system, each ring comprising 3 to 7, preferably 3, 5 or 6 members, and optionally substituted by one or more (C1-C8)alkyls, ora saturated or unsaturated and non-aromatic heterocycle, each ring comprising 3 to 7, preferably 5 or 6 links, and comprising one or more, in particular one or 2, heteroatoms chosen from oxygen, sulfur and nitrogen, and optionally substituted by one or more (C1-C8)alkyls, or an aryl, aryl-(C1-C6)alkyl, heteroaryl, or heteroaryl-(C1-C6)alkyl group,said group being optionally substituted by one or more substituents chosen from a halogen atom, a (C1-C8)alkyl, a (C1-C6)alkoxy and a (C1-C6)haloalkyl,- X is an oxygen atom or an NR' group, with R' representing a hydrogen atom or a (C1-C4)alkyl, and- n is equal to 0 or 1,for its antifungal and / or antibacterial activity on fungi and / or oomycetes and / or pathogenic bacteria of plants and crop seeds.
2. Use according to claim 1, in which R represents a (C1-C20)alkyl, preferably (C1-C15)alkyl, even more preferably (C1-C12)alkyl such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, 2-ethylpentyl or even 2-ethylhexyl.
3. Use according to claim 1, wherein R represents a heteroalkyl, with one or more heteroatoms selected from oxygen, sulfur, nitrogen or phosphorus, preferably oxygen, such as methoxyethyl.
4. Use according to claim 1, wherein R represents a saturated or unsaturated and non-aromatic hydrocarbon-based cyclic or polycyclic system, each ring comprising 3 to 7, preferably 5 or 6 members, and optionally substituted by one or more (C1-C8)alkyls, in particular cyclopropyl, menthyl or cholesteryl, preferably cyclopropyl.
5. Use according to claim 1, in which R represents a (C1-C20)alkenyl, in particular (C1-C15)alkenyl, preferably (C1-C12)alkenyl, and even more preferably (C1-C6)alkenyl, such as a methylene, ethylene, propylene or butene, preferably propylene.
6. Use according to claim 1, in which R is an aryl, aryl-(C1-C6)alkyl group,heteroaryl, or heteroaryl-(C1-C6)alkyl, said group being optionally substituted by one or more substituents chosen from a halogen atom, a (C1-C8)alkyl, a (C1-C6)alkoxy and a (C1-C6)haloalkyl, such as a furyl, a phenyl, a chlorophenyl, a chlorobenzyl or a trifluoromethylbenzyl.
7. Use according to any one of the preceding claims, of a compound of formula (I) in which: - R represents a methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, ethylpentyl, ethylhexyl, methoxyethyl, cyclopropyl, propylene, furyl, phenyl, chlorophenyl, chlorobenzyl or trifluoromethylbenzyl, and -n is equal to 0 or 1.
8. Use according to any one of the preceding claims, of a compound of formula (I) in which: - R represents a methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl,-n is equal to 0 or 1.
9. Use according to any one of the preceding claims, wherein said fungi and / or oomycetes pathogenic to plants and crop seeds are fungi pathogenic to plants and crop seeds of the genera Zymoseptoria, Fusarium, Sclerotinia, Botrytis, Alternaria, in particular chosen from the group consisting of Zymoseptoria tritici, Fusariumoxysporum, Fusarium solani, Fusarium avenaceum, Fusarium culmorum, Fusarium graminearum, Fusarium moniliforme, Fusarium poae, Fusarium proliferatum, Fusarium sporotrichioides, Fusariumsubglutinans, Fusarium tricinctum, Sclerotinia borealis, Sclerotinia bulborum, Sclerotinia minor, Sclerotinia ricini, Sclerotinia sclerotiorum, Sclerotinia spermophila, Sclerotinia trifoliorum, Botrytisallii, Botrytis anthophila, Botrytis cinerea, Botrytis fabae, Botrytis narcissicola, Alternia alternata, Alternaria solani and Alternaria brassisicola, preferably chosen from the Zymoseptoria tritici group,Fusarium solani, Sclerotinia sclerotiorum, Botrytis cinerea and Alternaria alternata.
10. Use according to any one of the preceding claims, wherein said pathogenic bacteria of plants and crop seeds are pathogenic bacteria of plants and crop seeds of the genera Erwinia, Pseudomonas, Ralstonia, Agrobacterium, Xanthomonas, Xylella, Dickeya, Pectobacterium, Clavibacter, and Candidatus, in particular selected from the group consisting of Erwinia persicina, Erwinia amylovora, Pseudomonas syringae, Ralstoniasolanacearum, Agrobacterium tumefaciens, Xanthomonas oryzae, Xanthomonascampestris, Xanthomonas axonopodis, Xylella fastidiosa, Dickeya dadantii, Dickeya solani, Pectobacterium carotovorum, Pectobacterium atrosepticum, Clavibacter michiganensis, Clavibactersepedonicus, and Candidatus Liberibacter.
11. Use according to any one of the preceding claims,among the many plants and seeds of culture are particular choices in the group made up of grains such as greens, corn, orgies, rice, soya, fruits and vegetables such as grapes, carrots, tomatoes, pêchers, apricots, tomatoes, radishes, haricots, vines and plants d'ornament, in particular choices in the group constitué des genres 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, 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, Currant, Castor, Rose, Rubus, Saccharum, Scorzonera, Secale Sechium, Sesamum, Setaria, Solanum, Sorghum, Spinacia, Theobroma, Tragopogon, Trifolium, Trigonella, Triticum, Urena, Vaccinium, Valerianella, Vanilla, Vicia, Vigna, Vigna, Xantho, Xanthoma Zea, Zingiber.
12. A process for combating fungi and / or oomycetes and / or bacterial pathogens of crop plants and seeds, comprising a step of applying a compound of claim (I) as defined in claims 1 to 8. 13.Method for controlling fungi, oomycetes and / or pathogenic bacteria in plants and crop seeds according to claim 12, comprising the following steps: (a) Mixing one or more compounds of formula (I) as defined in claims 1 to 8, with n being equal to 0 or 1, in a solvent, preferably aqueous based, which may contain additives such as alcohols or compatibilizers such as DMSO and / or surfactants; (b) Applying this mixture to the crop plants and / or coating said seeds with this mixture.
14. Method for controlling fungi and / or oomycetes and / or pathogenic bacteria in plants and crop seeds according to claim 12 or 13, wherein said mixture is applied at a dose ranging from 500 mg / L to 1 g / L for a treated surface ranging from 0.5 to 5 m2. 15.Method for controlling fungi and / or oomycetes and / or pathogenic bacteria of plants and crop seeds according to claims 12 to 14, wherein said mixture is applied at a frequency of 1 to 3 times per week.
16. Method for controlling fungi and / or oomycetes and / or pathogenic bacteria of plants and crop seeds according to claims 12 to 15, curative or preventive.
17. Composition for controlling fungi and / or oomycetes and / or pathogenic bacteria of plants and crop seeds comprising one or more compound(s) of formula (I) as defined in claims 1 to 8, and at least one acceptable excipient.
18. Composition according to claim 17, in which the amount of compound(s) of formula (I) is between 500 and 1000 mg / mL, preferably 600 and 1000 mg / mL, even more preferably 800 and 1000 mg / mL.
19. Composition for combating fungi and / or oomycetes and / or pathogenic bacteria of plants and crop seeds according to claims 17 to 18, wherein the at least one excipient is at least one surfactant, preferably at least one non-ionic surfactant such as polyoxyethylene sorbitan monolaurate, or alkyl-glycopyranosides.
20. Composition according to claims 17 to 19 further comprising another antifungal compound, preferably chosen from the group consisting of triazoles such as mefentrifluconazole, prothioconazole, metconazole for example; strobilurins such as bixafen, fluxapyroxad, benzovindiflupyr, fluopyram, penthiopyrad or boscalid; picolinamides or multisite compounds.
21. Compound of the following formula (I): wherein R, X and n are as defined in claims 1 to 8.
22. A compound of formula (I) according to claim 21 wherein:- X is an oxygen atom.
23. A compound of formula (I) according to claim 21 or 22, with n and R as defined in claims 1 to 8, except when n is 0 and R represents methyl, propyl, etheptyl.
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