Method for controlling or preventing Panama disease in banana plants

Abstract

The present invention provides a method for controlling or preventing Panama disease in banana plants, comprising administering to a plant a compound of formula (I) [Formula 1] TIFF2023511715000016.tif45160 (wherein R1, R2, R3, R4, R5, Y, A, B are as defined herein) to a crop of banana plants or the locus thereof.

Description

[Technical field]

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

[0002] Panama disease is also called Fusarium wilt of bananas. This disease is the most threatening disease to banana production. The disease was first observed in the banana cultivar "Gros Michel" shortly after the "banana industry" was established in the 1890s. Over the next 60 years, the wilt spread rapidly throughout the banana-growing regions, wilting banana plants despite all efforts. The identified pathogen of the disease was a fungus called Fusarium oxysporum f.sp. (forme specialis) cubense (Foc). In the 50s of the 20th century, relief came with the adaptation of a resistant banana cultivar: "Cavendish". Unfortunately, shortly after the introduction of Cavendish, the Taiwanese Cavendish clones succumbed again to a new strain of Foc causing wilt disease. The new strain pathogenic to Cavendish is now known as Tropical species 4 (TR4), whereas the Foc strain pathogenic to Gros Michel was called species 1. Recently, Foc TR4 was renamed Fusarium odoratissium (Maryani, Lombard et al., 1992, Stud. Mycol., 155-194). The strain spread slowly, during which it reached Southeast Asian countries, Australia, the Middle East, India, and Africa (Ordonez, Seidl et al. 2015, PLoS Pathog, 11(11)). The main vector for the spread of Foc TR4 is humans (Marquardt 2001). Although the elimination of the pathogen from new areas should be the most important line of defense, international trade, movement of workers, equipment, and plant material are major contributors to the rapid global spread of this banana pathogen. Unawareness is at the heart of local transmission. This applies to the behavior of banana farm personnel, the lack of disinfectant baths, the availability of equipment washing facilities, and the transportation of infected materials without proper disinfection measures. As Foc TR4 is a soil-borne disease, there are no proven 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 so far, control has been limited to phytosanitary measures (Ploetz, RC (2015). "Fusarium Wilt of Banana." Phytopathology 105(12):1512-1521). Summary of the Invention [Means for solving the problem]

[0003] Therefore, there is a strong need for further treatments against Panama disease. The present invention provides an improved method for controlling or preventing Panama disease in banana plants caused by the phytopathogenic microorganism Fusarium oxysporum f.sp. (formae specialis) cubense (Foc) (particularly Foc tropical species 4, i.e. Fusarium odoratissium). Thus, the present invention provides an important tool for banana farmers to control or prevent Panama disease. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0004] Cyclobutylcarboxamide compounds, and processes for their preparation, have been disclosed in WO 2013 / 143811 and WO 2015 / 003951. It has now been surprisingly discovered that certain cyclobutylcarboxamide compounds disclosed in WO 2013 / 143811 and / or WO 2015 / 003951 are highly effective in controlling or preventing Panama disease in banana plants caused by the phytopathogenic microorganism Fusarium oxysporum f.sp. (forme specialis) cubense (Foc) (particularly Foc tropical species 4, i.e. Fusarium odoratissium). This highly effective compound therefore represents an important novel solution for farmers to control or prevent Panama disease in banana plants.

[0005] Thus, in a first embodiment, there is provided a method for controlling or preventing damage to banana plants caused by the phytopathogenic microorganism Fusarium oxysporum f.sp. (formae specialis) cubense (Foc), in particular Foc tropical species 4, i.e. Fusarium odoratissium, comprising the steps of: [ka] (In the formula, Y is O, C=O, or CR12R13; A is a 5- or 6-membered aromatic heterocycle containing 1-3 heteroatoms each independently selected from oxygen, nitrogen, and sulfur, or a phenyl ring; the aromatic heterocycle or the phenyl may be optionally substituted with one or more R6; R6 are each independently selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-haloalkylthio, C1-C4-alkoxy-C1- C 4-alkyl, or C1-C4-haloalkoxy-C1-C4-alkyl; 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; R5 is hydrogen, methoxy, or hydroxyl; B is phenyl substituted with one or more R8; R8 are, independently of one another, halogen, cyano or a group -L-R9, where each L is, independently of the other, a bond, -O-, -OC(O)-, -NR7-, -NR7CO-, -NR7S(O)n-, -S(O)n-, -S(O)nNR7-, -COO- or CONR7-; n is 0, 1, or 2; R7 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, benzyl or phenyl, benzyl and phenyl being unsubstituted or substituted by halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl, R9 are each independently C1-C6 alkyl. So, C1-C6-alkyl, C3-C6-cycloalkyl, unsubstituted or substituted by one or more R10; So, C3-C6-cycloalkyl, C6-C14-bicycloalkyl, which is unsubstituted or substituted by one or more R10. So, C6-C14-bicycloalkyl, C2-C6-alkenyl, which is unsubstituted or substituted by one or more R10. So, C2-C6-alkenyl, C2-C6-alkynyl, which is unsubstituted or substituted by one or more R10; So, C2-C6-alkynyl, phenyl, which is unsubstituted or substituted by one or more R10. So, phenyl or heteroaryl, which is unsubstituted or substituted by R10; So, heteroaryl which is unsubstituted or substituted by one or more R; R10 are, independently of one another, 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, where B and A-CO-NR5 are cis to each other on the four-membered ring. or a salt or N-oxide thereof, or a tautomer or stereoisomer of this compound to a crop of banana plants or the locus thereof.

[0006] A more preferred method according to embodiment 1 is illustrated in the following embodiment.

[0007] As a second embodiment, Y is O or CH2; A is a 6-membered aromatic heterocycle or phenyl ring containing 1 to 2 nitrogen atoms, the aromatic heterocycle or phenyl being optionally substituted by one or more R6; R6 are, independently of each other, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-haloalkoxy; R1, R2, R3, R4 and R5 are each hydrogen; B is phenyl substituted by one or more R8; The method according to embodiment 1 is provided, wherein R8 are independently selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy and C3-C6-cycloalkyl.

[0008] In embodiment 3, there is provided the method of embodiment 1 or embodiment 2, wherein A is a 6-membered aromatic heterocycle containing 1-2 nitrogen atoms and having 1-3 substituents selected from R6, or a phenyl ring having 1 or 3 substituents selected from R6.

[0009] As embodiment 4, there is provided the method of any one of embodiments 1 to 3, wherein B is phenyl substituted with 1 to 3 substituents R8.

[0010] As a fifth embodiment, B is phenyl substituted by 1 to 3 substituents independently selected from fluoro, chloro, trifluoromethyl, cyclopropyl, difluoromethoxy, and trifluoromethoxy; The method of any one of embodiments 1-4 is provided, wherein A is phenyl, pyridyl, or pyrazinyl, the rings of which are, independently of each other, unsubstituted or substituted by one to three substituents independently selected from chloro, bromo, fluoro, methyl, cyano, and trifluoromethyl; Y is O or CH; and R1, R2, R3, R4, and R5 are each hydrogen.

[0011] As a sixth embodiment, Y is CH2, B is mono- or di-halogen substituted phenyl; A is selected from phenyl, pyrazinyl and pyridyl, each of which is mono- or di-substituted by substituents independently selected from halogen and C1-C4-haloalkyl; The method of any one of embodiments 1 to 5 is provided, wherein R1, R2, R3, R4 and R5 are each hydrogen.

[0012] The compound of formula (I) disclosed in any one of embodiments 1-6 may be a cis racemate, in which the left phenyl ring and the right AC(=O)-NH group are cis to each other on the cyclobutyl ring: [ka] Represents.

[0013] Thus, a racemic compound of formula (I) is a 1:1 mixture of compounds of formulas (Ia) and (Ib). The wedged bonds shown in compounds of formulas (Ia) and (Ib) represent absolute stereochemistry, while bold straight bonds such as those shown for compounds of formula (I) represent relative stereochemistry in a racemic compound.

[0014] It has also been surprisingly found that one enantiomer of the compound of formula (I) is particularly useful in controlling or preventing damage to banana plants caused by the phytopathogenic microorganism Pseudocercospora fijiensis.

[0015] Thus, in embodiment 7, the compound has the formula (Ia) [ka] The method according to any one of embodiments 1 to 6 is provided, wherein

[0016] Those skilled in the art will recognize that the compound of formula (Ia) is generally applied as part of a pesticidal composition according to the method described in embodiment 2. Thus, as embodiment 8, there is provided a method for controlling or preventing damage to banana plants caused by the phytopathogenic microorganism Pseudocercospora fijiensis, comprising applying to the banana plant or its locus a pesticidal composition comprising a compound according to any one of embodiments 1 to 7 and one or more formulation auxiliaries. As embodiment 9, there is provided a method for controlling or preventing damage to banana plants caused by the phytopathogenic microorganism Pseudocercospora fijiensis, comprising applying to the banana plant or its locus a pesticidal composition comprising a compound of formula (Ia) and one or more formulation auxiliaries. In the method according to embodiment 9, in the pesticidal composition comprising both the compound of formula (Ia) and the 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 the compound of formula (Ia) to the compound of formula (Ib) is greater than 1.5: 1, more preferably greater than 2.5: 1, particularly greater than 4: 1, advantageously greater than 9: 1, desirably greater than 20: 1, particularly greater than 35: 1.

[0017] It is also understood that mixtures containing 50% or less, preferably 40% or less, more preferably 30% or less, in particular 20% or less, advantageously 10% or less, desirably 5% or less, in particular 3% or less of the trans stereoisomer of the compound of formula (I) (i.e., in which the B and AC(=O)-NH groups are trans relative to each other) are part of the present invention. Preferably, the ratio of the compound of formula (I) to its trans isomer is greater than 1.5:1, more preferably greater than 2.5:1, in particular greater than 4:1, advantageously greater than 9:1, desirably greater than 20:1, in particular greater than 35:1.

[0018] Preferably, in a composition comprising a compound of formula (Ia), its trans isomer (i.e. in which the B and A-CO-NR2 groups are trans relative to each other) and a compound of formula (Ib), the composition comprises a compound of formula (Ia) in a concentration of at least 50%, more preferably 70%, even more preferably 85%, in particular more than 90%, particularly preferably more than 95%, based on the total amount of the compound of formula (Ia), its trans isomer and the compound of formula (Ib), respectively.

[0019] Further, as a tenth embodiment, there is provided a method for controlling or preventing damage to banana plants caused by the phytopathogenic microorganism Pseudocercospora fijiensis, comprising administering to a crop of banana plants or the locus thereof a compound represented by the formula (Ic) [ka] (In the formula, R11 and R12 are independently selected from halogen; A is halogen and C 1 ~C 4 -pyridyl substituted by 1 or 2 substituents independently selected from haloalkyl A method is provided comprising the step of applying a compound according to

[0020] As an eleventh embodiment, R11 and R12 are independently selected from chloro and fluoro; A is one or two Cs 1 ~C 4 The method of embodiment 10 is provided, wherein the pyrid-2-yl or pyrid-3-yl is substituted by a -haloalkyl substituent.

[0021] As embodiment 12, A is, [ka] is selected from R13 is C 1 ~C 412. The method of embodiment 10 or 11, wherein -haloalkyl, preferably trifluoromethyl, is provided.

[0022] In embodiment 13, the compound has formula (Ic): [ka] The method according to any one of embodiments 10 to 12, wherein R11, R12 and A are as defined in the following table, is provided.

[0023] [Table 1]

[0024] As a fourteenth embodiment, the method according to any one of the first to thirteenth embodiments, Providing a composition comprising a compound as defined in any one of embodiments 1 to 13; applying the composition to a crop of banana plants or to the locus thereof. A method is provided that includes:

[0025] 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 damage to banana plants by the phytopathogenic microorganism Fusarium oxysporum f.sp. (formae specialis) cubense (Foc), in particular Foc tropical species 4, i.e. Fusarium odoratissium.

[0026] As Embodiment 16, there is provided the use of a compound defined in any one of Embodiments 1 to 13 for controlling or preventing damage to banana plants caused by the plant pathogenic microorganism Fusarium oxysporum f. sp. cubense (Foc) (in particular, Foc tropical race 4, i.e., Fusarium odoratissium).

[0027] As Embodiment 17, there is provided a method for cultivating banana plants, Embodiment which comprises applying to the banana plants or treating the banana plants with a compound defined in any one of Items 1 to 13.

[0028] Preferably, the methods and uses described in any one of Embodiments 1 to 17 are carried out by drench application.

[0029] The preparation of the compounds defined in the methods described in any one of Embodiments 1 to 13 is disclosed in International Publication No. WO 2013 / 143811 and International Publication No. WO 2015 / 003951, which are incorporated herein by reference.

[0030] Definition: The term "halogen" represents fluoro, chloro, bromo or iodo, particularly fluoro, chloro or bromo.

[0031] As used herein, the term "alkyl" or "alk", alone or as part of a larger group (such as alkoxy, alkylthio, alkoxycarbonyl and alkylcarbonyl), is linear or branched, for example methyl, ethyl, n-propyl, n-butyl, isopropyl, sec-butyl, isobutyl, tert-butyl, pentyl, iso-pentyl or n-hexyl. The alkyl group is preferably a C 1 ~C 4 -alkyl group.

[0032] "Haloalkyl" as used herein refers to an alkyl group as defined above that is substituted with one or more of the same or different halogen atoms, e.g., CF 3 , C.F. 2 Cl, CF 2 H, CCl 2 H, F.C.H. 2 , ClCH 2 ,BrCH 2 , C.H. 3 CHF, (CH 3 ) 2 C.F., C.F. 3 CH 2 or CHF 2 CH 2 It is.

[0033] The methods and uses according to any one of embodiments 1 to 17 are preferably for controlling or preventing damage to crops by the phytopathogenic microorganism Fusarium oxysporum f.sp. (formae specialis) cubense (Foc), in particular Foc tropical species 4, i.e. Fusarium odoratissium, which is resistant to other fungicides. A Fusarium oxysporum f.sp. (forme specialis) cubense (Foc) (especially Foc tropical species 4, i.e. Fusarium odoratissium) that is "resistant" to a particular fungicide refers to a strain of the fungus of the genus Cercospora that is less susceptible to this fungicide compared to the expected susceptibility of the same Fusarium oxysporum f.sp. (forme specialis) cubense (Foc) fungus. This expected susceptibility may be determined, for example, using a strain that has never been exposed to this fungicide before.

[0034] The application of the method or use according to any one of the embodiments 1 to 17 is preferably to a crop of banana plants or to a locus thereof. Preferably, the application is to a crop of banana plants. The application of the compound of the present invention may be carried out according to any of the usual application modes (e.g. foliar, irrigation, soil, in furrow, etc.). Preferably, the application of the method or use according to any one of the embodiments 1 to 17 is carried out by irrigation application.

[0035] The compound 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 to 250 g AI / ha).

[0036] The compounds according to any one of the embodiments 1 to 13 are suitable for use on any banana plant, including those genetically modified to tolerate active ingredients such as herbicides, or to generate biologically active compounds to control damage caused by plant pests.

[0037] Generally, the compound according to any one of embodiments 1 to 13 is used in the form of a composition (eg, a formulation) containing a carrier. The compounds and compositions thereof according to any one of the embodiments 1 to 13 may be used in various forms such as aerosol dispensers, capsule suspensions, cold fog concentrates, dusts, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, encapsulated granules, fine granules, flowables for seed treatment, (pressurized) gas, gas generators, granules, hot fog concentrates, large granules, fine granules, oil dispersible powders, oil miscible flowables, oil miscible liquids, pastes, plant sticks, powders for dry seed treatment, pesticide-coated seeds, soluble concentrates, soluble powders, liquids for seed treatment, suspension concentrates (flowables), liquids for microdispersion (ulv), suspensions for microdispersion (ulv), water dispersible granules or water dispersible tablets, wettable powders for slurry treatment, water-soluble granules or water-soluble tablets, water-soluble powders and wettable powders for seed treatment.

[0038] The formulation typically comprises a liquid or solid carrier and one or more conventional formulation auxiliaries, which may optionally be solid or liquid auxiliaries, such as non-epoxidized or epoxidized vegetable oils (e.g., epoxidized coconut oil, rapeseed oil or soybean oil), antifoaming agents, such as silicone oils, preservatives, clays, inorganic compounds, viscosity regulators, surfactants, binders and / or tackifiers.The composition may not only comprise a combination of the compound of the present invention with one or more other biologically active substances, such as bactericides, fungicides, nematocides, plant activators, acaricides and insecticides, but may also further comprise fertilizers, micronutrient donors or other preparations that affect the growth of banana plants.

[0039] 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 of the invention, and in the presence of at least one auxiliary, for example by intimately mixing the compound of the invention with one or more auxiliaries and / or grinding it. In the case of the solid compounds of the invention, grinding / milling of the compound is carried out to ensure a specific particle size.

[0040] Examples of compositions for agricultural use are emulsifiable concentrates, suspension concentrates, microemulsions, oil-dispersible directly sprayable or dilutable solutions, spreadable pastes, dilute emulsifiable concentrates, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymeric substances, which comprise - at least - a compound according to any one of the embodiments 1 to 13, the type of composition being selected according to the intended purpose and the circumstances at hand.

[0041] Typically, the composition comprises 0.1-99%, in particular 0.1-95%, of a compound according to any one of the embodiments 1-13 and 1-99.9%, in particular 5-99.9%, of at least one solid or liquid carrier, and typically 0-25%, in particular 0.1-20%, of the composition can be surfactants (% means in each case percent by weight). Although concentrated compositions tend to be preferred for commercial purposes, end consumers usually use dilute compositions with a fairly low concentration of active ingredient.

[0042] Examples of foliar formulation types for premix compositions are as follows: GR: Granules WP: Water dispersible agent WG: Hydrable granule (powder) SG: Water-soluble granules SL: Soluble thickener EC: Emulsifiable concentrate EW: Oil in water emulsion ME: Microemulsion SC: Aqueous suspension concentrate CS: Aqueous capsule suspension OD: oil-based suspension concentrate, and SE: aqueous suspo-emulsion.

[0043] Meanwhile, examples of seed treatment formulation types for premix compositions are as follows: WS: Wettable powder for seed treatment slurry LS: Liquid for seed treatment ES: Emulsion for seed treatment FS: Suspension concentrate for seed treatment WG: Water-dispersible granules, and CS: Aqueous capsule suspension.

[0044] Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions or mixtures thereof and dusts.

[0045] The nature of the formulation as well as the method of application, whether foliar application, irrigation, spraying, misting, dusting, spreading, painting or pouring, will be selected according to the intended purpose and the prevailing conditions.

[0046] Tank-mix compositions are generally prepared by diluting one or more pre-mix compositions containing different pesticides and, optionally, further auxiliaries, with a solvent (eg, water).

[0047] Suitable carriers and adjuvants can be solid or liquid and are substances commonly used in formulation technology, such as natural or recycled mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.

[0048] Generally, tank mix formulations for foliar or soil application contain 0.1 - 20%, particularly 0.1 - 15%, of the desired component and 99.9 - 80%, particularly 99.9 - 85%, of solid or liquid adjuvants (including solvents such as water), and the adjuvants can be surfactants in an amount of 0 - 20%, particularly 0.1 - 15%, based on the tank mix formulation.

[0049] Typically, premix formulations for foliar application contain 0.1 - 99.9%, particularly 1 - 95%, of the desired component and 99.9 - 0.1%, particularly 99 - 5%, of solid or liquid adjuvants (including solvents such as water), and the adjuvants can be surfactants in an amount of 0 - 50%, particularly 0.5 - 40%, based on the premix formulation.

[0050] Normally, tank mix formulations for seed treatment application contain 0.25 - 80%, particularly 1 - 75%, of the desired component and 99.75 - 20%, particularly 99 - 25%, of solid or liquid adjuvants (including solvents such as water), and the adjuvants can be surfactants in an amount of 0 - 40%, particularly 0.5 - 30%, based on the tank mix formulation.

[0051] Typically, premix formulations for seed treatment application contain 0.5 - 99.9%, particularly 1 - 95%, of the desired component and 99.5 - 0.1%, particularly 99 - 5%, of solid or liquid adjuvants (including solvents such as water), and the adjuvants can be surfactants in an amount of 0 - 50%, particularly 0.5 - 40%, based on the premix formulation.

[0052] Commercially available products will preferably be formulated as concentrates (e.g., premix compositions (formulations)), but the end user will typically use diluted formulations (e.g., tank mix compositions).

[0053] The preferred seed treatment premix formulation is an aqueous suspension concentrate.The formulation can be applied to seeds using conventional treatment techniques and machines, such as fluidized bed technology, roller mill method, rotostatic seed treater and drum coater.Other methods, such as spouted bed, can also be useful.Seeds can be pre-classified before application.After application, seeds are typically dried and then transferred to a classifier for classification.Such procedures are known in the art.The compounds of the present invention are particularly suitable for use in soil and seed treatment applications.

[0054] In general, the premix compositions of the invention contain 0.5 to 99.9, in particular 1 to 95, advantageously 1 to 50% by weight of the desired component and 99.5 to 0.1, in particular 99 to 5% by weight of a solid or liquid auxiliary (including, for example, a solvent such as water), the auxiliary (or auxiliary) being a surfactant in an amount of 0 to 50, in particular 0.5 to 40% by weight, based on the weight of the premix formulation.

[0055] The invention will now be illustrated by the following non-limiting examples, all citations are incorporated by reference. EXAMPLES

[0056] Biological Examples Efficacy of different fungicide treatments against Panama disease (Fusarium odoratissium) in bananas A banana greenhouse trial was carried out in 2018 to evaluate the efficacy of a compound defined in any one of embodiments 1-13 against Fusarium odoratissium (Fusarium oxysporum f.sp. (Formella specialis) cubense tropical species 4) in banana.

[0057] The Fusarium oxysporum f.sp. cubense strains and tissue isolates of Fusarium oxysporum f.sp. cubense tropical race 4 (Foc TR4, strain II5) used in this study were obtained from the Wageningen University (The Netherlands) and Research collection. 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 over a period of three months. The chlamydospore density was determined by sowing, and the spore density was adjusted so that soil in the greenhouse containing 100,000 chlamydospores / gram was obtained.

[0058] Tissue culture plantlets of banana (Cavendish, Grand Naine) were transferred to small pots containing standard soil (5% peat, 41% crushed clay granules, 5% garden peat, 4% beam structure, 33% steam-treated compost 140), and acclimated to the climate by maintaining at 28 °C and approximately 100% relative humidity (RH) for two weeks. Subsequently, the relative humidity was reduced to approximately 90%.

[0059] The plants were cultivated for three months in the spring of 2018. The plants were uprooted and then infected by replanting them in a 2-liter volume of soil infested with chlamydospores. Subsequently, the plants were individually dipped in compound 1 (see embodiment 13) or water to avoid dilution or runoff of compound 1 and Foc TR4 chlamydospores. The plants were harvested in October after 20 weeks to allow the longest incubation time.

[0060] At harvest, the latter was evaluated for the incidence of Panama disease.

[0061]

Table 2

[0062] evaluation: Twenty weeks after transplanting, infection levels were determined by analyzing the corms of each plant.

[0063] [Table 3]

[0064] Conclusion: When 100,000 chlamydospores / ml were applied, all but the uninfected control plants (check) were infected. Under these conditions, compound 1 at 200 g / ha caused no visible or quantitative infection among the seven plants in this batch.

[0065] All treatments with compound 1 (100 or 200 g / ha) reduced the number of infected plants, indicating that compound 1 could potently reduce the infection of Foc TR4 chlamydospores in banana plants. Infected plants treated with compound 1 showed only low infection levels.

Claims

1. A method for controlling or preventing damage to banana plants caused by the phytopathogenic microorganism Fusarium oxysporum f.sp. (formae specialis) cubense (Foc), comprising the step of: 【Chemistry 1】 (In the formula, R11, R12, and A are as shown in the following table. 【Table 1】 (as defined in or a tautomer or stereoisomer of said compound to a crop of banana plants or the locus thereof.

2. The method of claim 1, wherein R11 and R12 are Cl and A is 2-trifluoromethyl-pyrid-3-yl.

3. A method according to claim 1 or 2, wherein the compound of formula (Ic) is applied as part of a pesticidal composition, and the ratio of the compound of formula (Ic) to its enantiomer is greater than 1.5:

1.

4. The method according to any one of claims 1 to 3, wherein the plant pathogenic microorganism is Fusarium odoratissimum.

5. 5. The method according to any one of claims 1 to 4, wherein the method comprises irrigation application of a compound according to claim 1 or 2.

6. 3. A method of cultivating banana plants which comprises applying to or treating banana plants with a compound according to claim 1 or 2.

7. 3. Use of the compounds according to claims 1 or 2 for controlling or preventing damage to banana plants caused by the phytopathogenic microorganism Fusarium oxysporum f.sp. (formae specialis) cubense (Foc).

8. 3. Use of a compound according to claim 1 or 2 for controlling or preventing damage to banana plants caused by the phytopathogenic microorganism Fusarium odoratissium.

9. 9. Use according to claim 7 or 8, wherein the use of the compound according to claim 1 or 2 is a drench application.

Images