Methods for controlling or preventing Panama disease in banana plants

Abstract

The present invention relates to a method for controlling or preventing Panama disease in banana plants, said method comprising applying to a crop of banana plants or a locus thereof a compound according to formula (I), wherein R1, R2, R3, R4, R5, Y, A, B are as defined herein.

Description

Technical Field

[0001] The present invention relates to a method for controlling or preventing Panama disease in banana plants. Background Art

[0002] Panama disease is also known as Fusarium wilt of bananas. It is the disease that poses the greatest threat to banana production. The disease was first detected in the banana cultivar 'Gros Michel' in the 1890s, just after the establishment of the 'banana industry'. During the following 60 years, Fusarium wilt quickly spread throughout the banana production area, causing the death of banana plants despite all efforts. The identified causative agent of the disease is the fungus Fusarium oxysporum f.sp. (forma specialis) cubense (Foc). Relief was brought in the 1950s by the modification of a resistant banana cultivar: 'Cavendish'. Unfortunately, soon after the introduction of 'Cavendish', the 'Cavendish' clone in Taiwan, China, succumbed again to a new strain of Foc, causing Fusarium wilt. The new strain pathogenic to Cavendish is now known as Tropical Race 4 (TR4), while the Foc strain pathogenic to Gros Michel is known as Race 1. Recently, Foc TR4 was renamed Fusarium odoratissium (Maryani, Lombard et al., 1992, Stud. Mycol. [Mycological Research], 155-194). This strain is slowly spreading and has reached countries in Southeast Asia, Australia, the Middle East, India and Africa during this period (Ordonez, Seidl et al. 2015, PLoS Pathog [Public Library of Science Pathogens], 11 (11)). The main vector of Foc TR4 transmission is humans (Marquardt 2001). Excluding the pathogen from new areas should be the most important line of defense, however, international trade, the travel of workers, equipment and plant materials have greatly contributed to the rapid global spread of this banana pathogen. Lack of awareness is the bottom line of local spread. This applies to the behavior of banana farm personnel, the lack of disinfection pools, the availability of cleaning facilities for equipment, and the transportation of infected materials without appropriate disinfection measures. Because Foc TR4 is a soil-borne disease, there is a lack of proven and effective management strategies to control the disease. Once established in the soil, Foc spores can survive for decades. The pathogen is resistant to common fungicides and its control has so far been limited to phytosanitary measures (Ploetz, RC (2015). "Fusarium Wilt of Banana." Phytopathology 105(12): 1512-1521).

[0003] Therefore, further treatments for Panama disease are highly desirable. The present invention provides an improved method for controlling or preventing Panama disease in banana plants caused by the plant pathogenic microorganism Fusarium oxysporum Cuban special (Foc), particularly Foc tropical race 4 (i.e., Fusarium odoratissium). Therefore, the present invention provides an important means for banana farmers to control or prevent Panama disease. DETAILED DESCRIPTION

[0004] Cyclobutylcarboxamide compounds and methods for their preparation are disclosed in WO 2013 / 143811 and WO 2015 / 003951. It has now been surprisingly found that specific cyclobutylcarboxamide compounds disclosed in WO 2013 / 143811 and / or WO 2015 / 003951 are very effective in controlling or preventing Panama disease in banana plants caused by the plant pathogenic microorganism Fusarium oxysporum Cuban special (Foc), in particular Foc tropical race 4 (i.e. Fusarium odoratissium). Therefore, these very effective compounds provide farmers with an important new solution for controlling or preventing Panama disease in banana plants.

[0005] Thus, as in Example 1, there is provided a method for controlling or preventing banana plants from being infected by the plant pathogenic microorganism Fusarium oxysporum Cuban special type (Foc), in particular Foc tropical race 4 (i.e. Fusarium odoratissium), the method comprising applying to a crop of banana plants or a locus thereof a compound according to formula (I)

[0006]

[0007] in

[0008] Y is O, C=O or CR12R13;

[0009] A is a 5-membered or 6-membered heteroaromatic ring or a benzene ring, wherein the heteroaromatic ring contains 1 to 3 heteroatoms each independently selected from oxygen, nitrogen and sulfur; the heteroaromatic ring or the phenyl ring is optionally substituted with one or more R6;

[0010] R6 are independently halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-haloalkylthio, C1-C4-alkoxy-C1-C4-alkyl or C1-C4-haloalkoxy-C1-C4-alkyl;

[0011] R1, R2, R3, R4, R12 and R13 are independently of one another hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl,

[0012] R5 is hydrogen, methoxy or hydroxy,

[0013] B is phenyl substituted by one or more R8,

[0014] R8 are independently halogen, cyano or a group -L-R9, wherein each L is independently a bond, -O-, -OC(O)-, -NR7-, -NR7CO-, -NR7S(O)n-, -S(O)n-, -S(O)nNR7-, -COO- or CONR7-,

[0015] n is 0, 1, or 2,

[0016] R7 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, benzyl or phenyl, wherein benzyl and phenyl are unsubstituted or substituted by halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl,

[0017] R9 are independently of one another C1-C6-alkyl which is unsubstituted or substituted by one or more R10, C3-C6-cycloalkyl which is unsubstituted or substituted by one or more R10, C6-C14-bicycloalkyl which is unsubstituted or substituted by one or more R10, C2-C6-alkenyl which is unsubstituted or substituted by one or more R10, C2-C6-alkynyl which is unsubstituted or substituted by one or more R10, phenyl which is unsubstituted or substituted by one or more R10, or heteroaryl which is unsubstituted or substituted by one or more R10,

[0018] R10 are independently halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C3-C6-alkenyloxy, or C3-C6-alkynyloxy;

[0019] or a salt or N-oxide thereof;

[0020] Wherein B and A-CO-NR5 are cis relative to each other on the four-membered ring,

[0021] or tautomers or stereoisomers of these compounds.

[0022] A more preferred method according to Example 1 is given in the following examples.

[0023] As embodiment 2, a method according to embodiment 1 is provided, wherein

[0024] Y is O or CH2;

[0025] A is a 6-membered heteroaromatic ring or a benzene ring, wherein the heteroaromatic ring contains 1 to 2 nitrogen atoms; the heteroaromatic ring or the phenyl group is optionally substituted with one or more R6;

[0026] R6 are independently halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, or C1-C4-haloalkoxy;

[0027] R1, R2, R3, R4 and R5 are each hydrogen;

[0028] B is phenyl substituted by one or more R8;

[0029] R8 are independently selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy and C3-C6-cycloalkyl.

[0030] As Example 3, a method according to Example 1 or Example 2 is provided, wherein A is a 6-membered heteroaromatic ring or a benzene ring, the heteroaromatic ring contains 1 to 2 nitrogen atoms and has 1 to 3 substituents selected from R6, and the benzene ring has 1 or 3 substituents selected from R6.

[0031] As embodiment 4, provided is a method according to any one of embodiments 1 to 3, wherein B is phenyl substituted with 1 to 3 substituents R8.

[0032] As embodiment 5, there is provided a method according to any one of embodiments 1 to 4, wherein B is phenyl substituted with 1 to 3 substituents independently selected from fluoro, chloro, trifluoromethyl, cyclopropyl, difluoromethoxy and trifluoromethoxy;

[0033] A is phenyl, pyridyl or pyrazinyl, the rings of which are independently unsubstituted or substituted with 1 to 3 substituents independently selected from chlorine, bromine, fluorine, methyl, cyano and trifluoromethyl, Y is O or CH2, and R1, R2, R3, R4 and R5 are each hydrogen.

[0034] As embodiment 6, a method according to any one of embodiments 1 to 5 is provided, wherein

[0035] Y is CH2;

[0036] B is a mono- or di-halogen-substituted phenyl group;

[0037] A is selected from phenyl, pyrazinyl and pyridinyl, each of which is mono- or di-substituted by a substituent independently selected from halogen and C1-C4-haloalkyl;

[0038] R1, R2, R3, R4 and R5 are each hydrogen.

[0039] The compounds of formula (I) as disclosed in any one of Examples 1 to 6 represent cis racemates: the benzene ring on the left and the AC(=O)-NH group on the right are cis to each other on the cyclobutyl ring:

[0040]

[0041] Thus, the racemic compound of formula (I) is a 1:1 mixture of compounds of formula (la) and (lb). The wedge-shaped bonds shown in compounds of formula (la) and (lb) represent the absolute stereochemistry, while the thick straight bonds as shown for compounds of formula (I) represent the relative stereochemistry in the racemic compound.

[0042] It has also been surprisingly found that one enantiomer of the compound of formula (I) is particularly useful for controlling or preventing infection of banana plants by the phytopathogenic microorganism Pseudocercospora fijiensis.

[0043] Thus, as embodiment 7, there is provided a method according to any one of embodiments 1-6, wherein the compound has formula (Ia)

[0044]

[0045] The skilled person will know that according to the method described in Example 2, the compound of formula (Ia) is usually applied as part of a pesticidal composition. Therefore, as in Example 8, a method for controlling or preventing banana plants from being infected by the plant pathogenic microorganism Pseudocercospora fijiensis is provided, the method comprising applying a pesticidal composition to a banana plant crop or its site, the pesticidal composition comprising a compound according to any one of Examples 1-7 and one or more formulation adjuvants. As in Example 9, a method for controlling or preventing banana plants from being infected by the plant pathogenic microorganism Pseudocercospora fijiensis is provided, the method comprising applying a pesticidal composition to a banana plant crop or its site, the pesticidal composition comprising a compound of formula (Ia) and one or more formulation adjuvants. In the method according to Example 9, for the pesticidal composition comprising both a compound of formula (Ia) and a compound of formula (Ib), the ratio of the compound of formula (Ia) to its enantiomer (the compound of formula (Ib)) must be greater than 1:1. Preferably, the ratio of compounds of formula (Ia) to compounds of formula (Ib) is greater than 1.5:1, more preferably greater than 2.5:1, especially greater than 4:1, advantageously greater than 9:1, desirably greater than 20:1, in particular greater than 35:1.

[0046] Mixtures are also understood as part of the present invention, these mixtures contain up to 50%, preferably up to 40%, more preferably up to 30%, especially up to 20%, advantageously up to 10%, desirably up to 5%, in particular up to 3% of the trans stereoisomer of the compound of formula (I) (i.e. wherein B and AC(=O)-NH groups are trans to each other). Preferably, the ratio of the compound of formula (I) and its trans isomer is greater than 1.5:1, more preferably greater than 2.5:1, especially greater than 4:1, advantageously greater than 9:1, desirably greater than 20:1, in particular greater than 35:1.

[0047] Preferably, in a composition comprising a compound having formula (Ia), its trans isomer (i.e. wherein the B and A-CO-NR2 groups are trans to each other) and a compound having formula (Ib), the composition comprises a compound having formula (Ia) in a concentration of at least 50%, more preferably 70%, even more preferably 85%, in particular higher than 90%, and particularly preferably higher than 95%, each based on the total amount of the compound having formula (Ia), its trans isomer and the compound having formula (Ib).

[0048] In addition, as in Example 10, a method for controlling or preventing banana plants from being infected by the plant pathogenic microorganism Pseudocercospora fijiensis is provided, the method comprising applying a compound according to formula (Ic) to a banana plant crop or a locus thereof.

[0049]

[0050] in

[0051] R11 and R12 are independently selected from halogen;

[0052] A is pyridinyl substituted by one or two substituents independently selected from halogen and C1-C4-haloalkyl.

[0053] As embodiment 11, a method according to embodiment 10 is provided, wherein

[0054] R11 and R12 are independently selected from chlorine and fluorine;

[0055] A is pyridin-2-yl or pyridin-3-yl substituted by one or two C1-C4-haloalkyl substituents.

[0056] As embodiment 12, a method according to embodiment 10 or 11 is provided, wherein

[0057] A is selected from

[0058]

[0059] R13 is C1-C4-haloalkyl, preferably trifluoromethyl.

[0060] As embodiment 13, there is provided a method according to any one of embodiments 10 to 12, wherein the compound is selected from any one of compounds 1 to 12 having formula (Ic)

[0061]

[0062] Wherein R11, R12 and A are as defined in the following table:

[0063] Compound A R11 R12 1 2-Trifluoromethyl-pyridin-3-yl Cl Cl 2 3-Trifluoromethyl-pyridin-2-yl Cl Cl 3 3-Trifluoromethyl-pyridin-2-yl F F 4 3-Trifluoromethyl-pyridin-2-yl Cl F 5 3-Chloro-pyridin-2-yl Cl Cl 6 2-Methyl-pyridin-3-yl Cl Cl 7 2-Trifluoromethyl-pyridin-3-yl Cl F

[0064] As embodiment 14, a method according to any one of embodiments 1 to 13 is provided, wherein the method comprises the following steps

[0065] providing a composition comprising a compound as defined in any one of embodiments 1 to 13;

[0066] The composition is applied to a crop of banana plants or a locus thereof.

[0067] As embodiment 15, there is provided the use of a compound as defined in any one of embodiments 1 to 13 for controlling or preventing banana plants from being infected by the plant pathogenic microorganism Fusarium oxysporum Cuban special type (Foc), especially Foc tropical race 4 (ie Fusarium odoratissium).

[0068] As Example 16, there is provided the use of a compound as defined in any one of Examples 1 to 13 for controlling or preventing banana plants from being infected by the plant pathogenic microorganism Fusarium oxysporum Cuban special type (Foc), especially Foc tropical race 4 (ie Fusarium odoratissium).

[0069] As embodiment 17, there is provided a method for growing banana plants, the method comprising applying to the banana plants or treating the banana plants with a compound as defined in any one of embodiments 1 to 13.

[0070] Preferably, the method and use according to any one of embodiments 1 to 17 is performed by drenching application.

[0071] The preparation of compounds as defined in the method of any one of Examples 1 to 13 has been disclosed in WO 2013 / 143811 and WO 2015 / 003951, which are incorporated herein by reference.

[0072] definition:

[0073] The term "halogen" denotes fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.

[0074] The term "alkyl" as used herein alone or as part of a larger group such as alkoxy, alkylthio, alkoxycarbonyl and alkylcarbonyl is straight or branched and is, for example, methyl, ethyl, n-propyl, n-butyl, isopropyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl or n-hexyl. Alkyl is suitably C1-C4-alkyl.

[0075] As used herein, "haloalkyl" is an alkyl group as defined above substituted by one or more identical or different halogen atoms, and is, for example, CF3, CF2Cl, CF2H, CCl2H, FCH2, ClCH2, BrCH2, CH3CHF, (CH3)2CF, CF3CH2 or CHF2CH2.

[0076] The method and use according to any one of embodiments 1 to 17 are preferably used to control or prevent crops from being infected by plant pathogenic microorganisms Fusarium oxysporum Cuban specialization type (Foc), especially Foc tropical race 4 (i.e. Fusarium odoratissium) that are resistant to other fungicides. Fusarium oxysporum Cuban specialization type (Foc), especially Foc tropical race 4 (i.e. Fusarium odoratissium) that is "resistant" to a specific fungicide refers to, for example, a Cercospora fungal strain that is less sensitive to that fungicide compared to the expected sensitivity of the same Fusarium oxysporum Cuban specialization type (Foc) fungal species. The expected sensitivity can be measured using, for example, a strain that has not been previously exposed to a fungicide.

[0077] According to the method or use according to any one of embodiments 1 to 17, preferably banana plant crops or their sites are applied. Preferably, banana plant crops are applied. The application of the compound of the present invention can be carried out according to any common application mode (such as leaf application, drench application, soil application, in-furrow application, etc.). Preferably, the application according to the method or use according to any one of embodiments 1 to 17 is carried out by drench application.

[0078] The compound as defined in any one of embodiments 1 to 13 is preferably used in the method according to any one of embodiments 1 to 17 at 100 to 500 g active ingredient (AI) / hectare (ha), preferably 150-250 g AI / ha.

[0079] The compounds as defined in any one of embodiments 1 to 13 are suitable for use on any banana plant, including those that have been genetically modified to be resistant to active ingredients such as herbicides, or those that have been genetically modified to produce biologically active compounds that control infestation by plant pests.

[0080] Typically, the compound as defined in any one of Examples 1 to 13 is used in the form of a composition (eg, a formulation) containing a carrier. The compounds and compositions thereof as defined in any one of Examples 1 to 13 can be used in different forms, such as aerosol sprays, capsule suspensions, concentrated cold mists, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, encapsulated granules, fine granules, flowable concentrates for seed treatment, gases (under pressure), gas-producing products, granules, concentrated hot mists, large granules, microgranules, oil-dispersible powders, oil suspensions, oil-soluble liquids, pastes, plant sticks, powders for dry seed treatment, seeds coated with pesticides, soluble concentrates, soluble powders, solutions for seed treatment, suspension concentrates (flowable concentrates), ultra-low volume (ulv) liquids, ultra-low volume (ulv) suspensions, water-dispersible granules or tablets, water-dispersible powders for slurry treatment, water-soluble granules or tablets, water-soluble powders for seed treatment and wettable powders.

[0081] The formulation typically comprises a liquid or solid carrier and optionally one or more conventional formulation adjuvants, which may be solid or liquid adjuvants, for example, non-epoxidized or epoxidized vegetable oils (e.g., epoxidized coconut oil, rapeseed oil or soybean oil), defoamers (e.g., silicone oils), preservatives, clays, inorganic compounds, viscosity modifiers, surfactants, binders and / or tackifiers. The composition may further comprise fertilizers, micronutrient donors or other preparations that affect the growth of banana plants, and comprises combinations containing the compounds of the invention and one or more other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides and insecticides.

[0082] The compositions are prepared in a manner known per se, in the absence of auxiliaries, for example by grinding, sieving and / or compressing the solid compound according to the invention, and in the presence of at least one auxiliary, for example by intimately mixing and / or grinding the compound according to the invention with one or more auxiliary agents. In the case of the solid compounds according to the invention, the grinding / milling of the compound is to ensure a specific particle size.

[0083] Examples of compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersions, directly sprayable or dilutable solutions, spreadable pastes, diluted emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or capsules in a polymeric substance, these compositions comprising at least a compound as defined in any one of embodiments 1 to 13 and the type of composition being chosen to suit the intended purpose and the prevailing circumstances.

[0084] Typically, the composition comprises 0.1% to 99% (especially 0.1% to 95%) of a compound as defined in any one of Examples 1 to 13 and 1% to 99.9% (especially 5% to 99.9%) of at least one solid or liquid carrier, and it is usually possible that 0 to 25% (especially 0.1% to 20%) of the composition is a surfactant (% means percentage by weight in each case). Although for commercial products, concentrated compositions tend to be preferred, the final consumer usually uses a diluted composition with a significantly lower concentration of active ingredient.

[0085] Examples of leaf formulation types for use in premix compositions are:

[0086] GR: Granules

[0087] WP: Wettable Powder

[0088] WG: Water dispersible granules (powder)

[0089] SG: Water-soluble granules

[0090] SL: Soluble Concentrate

[0091] EC: Emulsifiable Concentrate

[0092] EW: Oil in water emulsion

[0093] ME: Microemulsion

[0094] SC: Aqueous Suspension Concentrate

[0095] CS: Aqueous Capsule Suspension

[0096] OD: Oil-based suspension concentrates, and

[0097] SE: aqueous suspension emulsion.

[0098] While examples of the types of seed treatment formulations useful in premix compositions are:

[0099] WS: Wettable powder for seed treatment slurry

[0100] LS: Solution for seed treatment

[0101] ES: Emulsion for seed treatment

[0102] FS: Suspension concentrate for seed treatment

[0103] WG: water dispersible granules, and

[0104] CS: aqueous capsule suspension.

[0105] Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions or mixtures thereof, and dusts.

[0106] In view of the nature of the formulation, the application method (such as foliar application, drenching application, spraying application, atomization application, dusting application, broadcasting application, coating application or pouring application) can be selected according to the intended purpose and the prevailing circumstances.

[0107] Tank-mix compositions are typically prepared by diluting one or more premix compositions containing different pesticides and, optionally, additional adjuvants with a solvent (eg, water).

[0108] Suitable carriers and adjuvants can be solid or liquid and are the substances customary in formulation technology, for example natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.

[0109] Generally, tank-mix formulations for foliar or soil application contain 0.1% to 20%, especially 0.1% to 15%, of the desired ingredients and 99.9% to 80%, especially 99.9% to 85%, of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 20%, especially 0.1% to 15%, based on the tank-mix formulation.

[0110] Typically, premix formulations for foliar application contain 0.1% to 99.9%, especially 1% to 95%, of the desired ingredient and 99.9% to 0.1%, especially 99% to 5%, of a solid or liquid adjuvant (including, for example, a solvent such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 50%, especially 0.5% to 40%, based on the premix formulation.

[0111] Typically, tank-mix formulations for seed treatment applications contain 0.25% to 80%, especially 1% to 75%, of the desired ingredients and 99.75% to 20%, especially 99% to 25%, of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 40%, especially 0.5% to 30%, based on the tank-mix formulation.

[0112] Typically, premix formulations for seed treatment applications contain 0.5% to 99.9%, especially 1% to 95% of the desired ingredients and 99.5% to 0.1%, especially 99% to 5%, of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant can be a surfactant, in an amount of 0 to 50%, especially 0.5% to 40%, based on the premix formulation.

[0113] Whereas commercial products will preferably be formulated as concentrates (eg, premix compositions (formulations)), the end user will typically use a diluted formulation (eg, a tank-mix composition).

[0114] Preferred seed treatment premix formulations are aqueous suspension concentrates. Conventional treatment techniques and machines, such as fluidized bed technology, drum milling methods, rotostatic seed treatment machines and drum coating machines, can be used to apply the formulation to the seeds. Other methods (such as spouted beds) may also be useful. The seeds may be pre-sized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art. The compound of the present invention is particularly suitable for use in soil and seed treatment applications.

[0115] Typically, the premix composition of the present invention contains 0.5% to 99.9%, especially 1% to 95%, advantageously 1% to 50% by mass of the desired ingredients and 99.5% to 0.1%, especially 99% to 5% by mass of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant (or adjuvant) may be a surfactant, in an amount of 0 to 50%, especially 0.5% to 40%, by mass, based on the mass of the premix formulation.

[0116] The invention will now be illustrated by the following non-limiting examples.All references cited are incorporated by reference.

[0117] Biological Examples

[0118] Effects of different fungicide treatments on Panama disease ( Fusarium odoratissium )

[0119] A banana greenhouse trial was conducted in 2018 to evaluate the efficacy of a compound as defined in any one of Examples 1 to 13 against Fusarium odoratissium (Fusarium oxysporum Cuban special tropical race 4) in banana.

[0120] The Fusarium oxysporum Cuban Specialty strains and tissue isolates Fusarium oxysporum Cuban Specialty Tropical Race 4 (Foc TR4, strain II5) used in this study were obtained from Wageningen University (Netherlands) and research collections. The strains were taken from liquid N2 cultures and grown on PDA (potato dextrose agar) plates. After verification by PCR (polymerase chain reaction) analysis, chlamydospores were produced within three months. The chlamydospore density was determined by plating and the spore density was adjusted to produce soil containing 100,000 chlamydospores / gram in the greenhouse.

[0121] Banana (Cavendish, Grand Naine) tissue culture seedlings were transferred to small pots containing standard soil (peat 5%, ground clay granules 41%, garden peat 5%, beam structure 4%, steamed 140 compost 33%) and maintained at 28°C and about 100% relative humidity (RH) for two weeks to acclimate. Thereafter, the relative humidity was reduced to about 90%.

[0122] During the spring of 2018, the plants were grown for 3 months. They were uprooted and then infected by replanting them in 2 liters of soil infected with chlamydospores. Thereafter, the plants were flooded with compound 1 (see Example 13) or water alone to avoid dilution or overflow of compound 1 and Foc TR4 chlamydospores. In order to allow the longest cultivation time, the plants were harvested in October after 20 weeks.

[0123] The latter were assessed for the development of Panama disease at harvest.

[0124] Table 1: Treatments performed.

[0125]

[0126] Evaluate:

[0127] 20 weeks after transplanting, the level of infestation was determined by analyzing the bulbs of each plant.

[0128]

[0129] in conclusion:

[0130] When 100,000 chlamydospores / ml were applied, all but one of the uninfected control plants (Control) were infected. Under these conditions, 200 g / ha of compound 1 did not produce a visual or quantifiable infection in the seven plants of this batch.

[0131] All treatments with compound 1 (100 or 200 g / ha) resulted in a reduction in the number of infected plants. This indicates that compound 1 is able to strongly reduce the infection of chlamydospores of Foc TR4 in banana plants. Infected plants treated with compound 1 showed only a low level of infection.

Claims

1. A method for controlling or preventing banana plants from being infected by the plant pathogenic microorganism Fusarium oxysporum Cuban type (Foc), the method comprising applying a compound of formula (Ic) to a banana plant crop or a locus thereof. 。 2. The method according to claim 1, wherein the plant pathogenic microorganism is Fusarium odoratissium.

3. The method according to claim 1 or 2, wherein: The method comprises drench application of a compound as defined in claim 1.

4. A method for growing banana plants, said method comprising applying to banana plants a compound as defined in claim 1 or treating said banana plants with said compound.

5. Use of a compound as defined in claim 1 for controlling or preventing infection of banana plants by the phytopathogenic microorganism Fusarium oxysporum genus Cubanosporum (Foc).

6. Use of a compound as defined in claim 1 for controlling or preventing infection of banana plants by the phytopathogenic microorganism Fusarium odoratissium.

7. The use according to claim 5 or 6, wherein The use of the compound as defined in claim 1 is by dredging.

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