Methods of controlling or preventing infestation of banana plants by phytopathogenic microorganisms of genus pseudocercospora

Abstract

To provide methods for controlling or preventing infestation of a banana plant by phytopathogenic microorganisms of the genus Pseudocercospora, (in particular Pseudocercospora fijiensis).SOLUTION: The present invention relates to methods for controlling or preventing infestation of a banana plant by phytopathogenic microorganisms of the genus Pseudocercospora, (in particular Pseudocercospora fijiensis), comprising applying to a crop of banana plants, the locus thereof, or propagation material thereof, a compound according to formula (I) wherein R1, R2, R3, R4, R5, Y, A, B are as defined herein.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a method for controlling or preventing damage to banana plants caused by phytopathogenic microorganisms of the genus Pseudocercospora.

Background Art

[0002] Worldwide, one of the most important diseases in banana production is Black Sigatoka disease caused by Pseudocercospora fijiensis. Black Sigatoka disease causes severe defoliation and indirect quality problems of fruits after harvest such as premature ripening of fruits. Plants with leaves damaged by Black Sigatoka disease may have a fruit yield reduction of up to 50%.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Means for Solving the Problems

[0004] The present invention provides an improved method for controlling or preventing damage to banana plants caused by phytopathogenic microorganisms of the genus Pseudocercospora (especially Pseudocercospora fijiensis). Thus, the present invention provides banana farmers with an important means for controlling or preventing damage caused by phytopathogenic microorganisms of the genus Pseudocercospora (especially Pseudocercospora fijiensis which causes Black Sigatoka disease). Cyclobutyl carboxamide compounds and methods for their preparation are disclosed in International Publication No. WO 2013 / 143811 and International Publication No. WO 2015 / 003951. Here, surprisingly, certain cyclobutyl carboxamide compounds disclosed in International Publication No. WO 2013 / 143811 and / or International Publication No. WO 2015 / 003951 have been found to be very effective in controlling or preventing damage to banana plants caused by phytopathogenic microorganisms of the genus Pseudocercospora, in particular Pseudocercospora fijiensis. Therefore, this very effective compound provides an important new solution for farmers to control or prevent damage to banana plants caused by phytopathogenic microorganisms of the genus Pseudocercospora, in particular Pseudocercospora fijiensis, and thus to address black Sigatoka, a serious banana disease.

Mode for Carrying Out the Invention

[0005] Accordingly, as Embodiment 1, there is provided a method for controlling or preventing damage to banana plants caused by phytopathogenic microorganisms of the genus Pseudocercospora, in particular Pseudocercospora fijiensis, which comprises applying to a banana plant crop, its location or its propagation material a compound of formula (I)

Chemical formula

[0006] A more preferred method according to Embodiment 1 is shown in the following embodiments.

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

[0008] As Embodiment 3, A is a 6-membered aromatic heterocyclic ring containing one or two nitrogen atoms and having 1 to 3 substituents selected from R6 or a phenyl ring having one or three substituents selected from R6, and the method according to Embodiment 1 or Embodiment 2 is provided.

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

[0010] As Embodiment 5, B is phenyl substituted with 1 to 3 substituents independently selected from fluoro, chloro, trifluoromethyl, cyclopropyl, difluoromethoxy and trifluoromethoxy, A is phenyl, pyridyl or pyrazinyl, and those rings are each independently unsubstituted or substituted with 1 to 3 substituents independently selected from chloro, bromo, fluoro, methyl, cyano and trifluoromethyl, Y is O or CH2, and R1, R2, R3, R4 and R5 are each hydrogen. There is provided the method according to any one of Embodiments 1 to 4.

[0011] As Embodiment 6, Y is CH2, B is mono- or di-halogen-substituted phenyl, A is selected from phenyl, pyrazinyl and pyridyl, and each of these is mono- or di-substituted with a substituent independently selected from halogen and C1-C4-haloalkyl, R1, R2, R3, R4 and R5 are each hydrogen. There is provided the method according to any one of Embodiments 1 to 5.

[0012] The compound of formula (I) disclosed in any one of Embodiments 1 to 6 is a cis racemic compound in which the left phenyl ring and the right A-C(=O)-NH group are cis to each other on the cyclobutyl ring:

Chemical formula

[0013] Therefore, the racemic compound of formula (I) is a 1:1 mixture of the compounds of formula (Ia) and (Ib). The wedge-shaped bonds shown in the compounds of formula (Ia) and (Ib) represent the absolute stereochemistry, while the thick straight-line bonds such as those shown for the compound of formula (I) represent the relative stereochemistry in the racemic compound.

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

[0015] Therefore, as Embodiment 7, the compound is of formula (Ia)

Chemical formula

[0016] Those skilled in the art recognize that the compounds of formula (Ia) are generally applied as part of a pesticidal composition according to the method described in Embodiment 2. Accordingly, as Embodiment 8, there is provided a method for controlling or preventing damage to banana plants caused by the phytopathogenic microorganism Pseudocercospora fijiensis, the method comprising applying to the crop, locus or propagation material of the banana plant a pesticidal composition comprising the compound according to any one of Embodiments 1 to 7 and one or more formulation aids. As Embodiment 9, there is provided a method for controlling or preventing damage to banana plants caused by the phytopathogenic microorganism Pseudocercospora fijiensis, the method comprising applying to the crop, locus or propagation material of the banana plant a pesticidal composition comprising the compound of formula (Ia) and one or more formulation aids. In the method according to Embodiment 9, in a 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 exceed 1:1. Preferably, the ratio of the compound of formula (Ia) to the compound of formula (Ib) is more than 1.5:1, more preferably more than 2.5:1, particularly more than 4:1, advantageously more than 9:1, desirably more than 20:1, particularly more than 35:1.

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

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

[0019] Furthermore, as Embodiment 10, a method for controlling or preventing damage to banana plants by the phytopathogenic microorganism Pseudocercospora fijiensis, comprising applying to a crop, location or propagation material of a banana plant a compound of formula (Ic)

Chemical formula

[0020] As Embodiment 11, R11 and R12 are independently selected from chloro and fluoro, A is pyrid-2-yl or pyrid-3-yl substituted by one or two C1-C4-haloalkyl substituents, and the method according to Embodiment 10 is provided.

[0021] As Embodiment 12, A is

Chemical formula

[0022] As Embodiment 13, the compound is of formula (Ic) [Chemical formula] selected from any one of Compounds 1 to 12, wherein R11, R12 and A are as defined in the following table, and the method according to any one of Embodiments 10 to 12 is provided.

[0023] [Table 1]

[0024] As Embodiment 14,[[]] - providing a composition comprising the compound according to any one of Embodiments 1 to 13; - applying the composition to the propagation material; - planting the propagation material and the method according to any one of Embodiments 1 to 13 is provided.

[0025] As Embodiment 15,[[]] - providing a composition comprising the compound according to any one of Embodiments 1 to 13; - applying the composition to the banana plant crop or its location and the method according to any one of Embodiments 1 to 13 is provided.

[0026] As Embodiment 16, the use of the compound according to any one of Embodiments 1 to 13 for controlling or preventing damage to banana plants by phytopathogenic microorganisms of the genus Pseudocercospora (especially Pseudocercospora fijiensis) is provided.

[0027] As Embodiment 17, there is provided the use of a compound according to any one of Embodiments 1 to 13 for controlling or preventing damage to banana plants caused by phytopathogenic microorganisms of the genus Pseudocercospora (especially Pseudocercospora fijiensis).

[0028] As Embodiment 18, there is provided a method for cultivating banana plants, the method comprising the step of applying or treating the banana plants or their propagation materials with a compound according to any one of Claims 1 to 13.

[0029] Preferably, the methods and uses according to any one of Embodiments 1 to 18 are carried out by drench application.

[0030] The preparation of the compounds as defined in the method according to 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.

[0031] Definition: The term "halogen" represents fluoro, chloro, bromo or iodo, especially fluoro, chloro or bromo.

[0032] 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 and is, for example, methyl, ethyl, n-propyl, n-butyl, isopropyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl or n-hexyl. The alkyl group is preferably a C1-C4-alkyl group.

[0033] As used herein, "haloalkyl" is an alkyl group as defined above, substituted with one or more of the same or different halogen atoms, such as CF3, CF2Cl, CF2H, CCl2H, FCH2, ClCH2, BrCH2, CH3CHF, (CH3)2CF, CF3CH2 or CHF2CH2.

[0034] The methods and uses according to any one of Embodiments 1 to 18 are preferably for controlling or preventing damage to crops by phytopathogenic microorganisms that are resistant to other fungicides. A "resistant" Cercospora fungus to a particular fungicide refers to a strain of Cercospora fungus that has a lower sensitivity to that fungicide compared to the predicted sensitivity of the same species of Cercospora fungus. The predicted sensitivity can be measured, for example, using strains that have not been previously exposed to the fungicide.

[0035] The application according to the method or use according to any one of Embodiments 1 to 18 is preferably directed to a crop of banana plants, its location or its propagation material. Preferably, the application is directed to a crop of banana plants or its propagation material, more preferably the propagation material. The application of the compounds of the present invention can be carried out according to any of the usual application forms, such as foliar application, irrigation, soil application, inter-row application, etc.

[0036] The compounds according to any one of Embodiments 1 to 13 are preferably used for pest control at 50 - 300 g active ingredient (AI) / ha, preferably 150 - 300 g AI / ha.

[0037] The compounds according to any one of Embodiments 1 to 13 are used for any peanut plant that has been genetically modified to be resistant to active ingredients such as herbicides, or are suitable for producing biologically active compounds for controlling damage caused by plant pests.

[0038] Generally, the compound according to any one of Embodiments 1 to 13 is used in the form of a composition (e.g., a formulation) containing a carrier. The compound according to any one of Embodiments 1 to 13 and its composition can be in various forms such as aerosol dispensers, capsule suspensions, cold smoke concentrates, powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, encapsulated granules, fine granules, flowables for seed treatment, (pressurized) gases, gas generators, granules, warm smoke concentrates, large granules, microparticles, oil-dispersible powders, oil-miscible flowables, oil-miscible liquids, pastes, plant sticks, powders for dry seed treatment, seeds coated with pesticides, soluble concentrates, soluble powders, liquids for seed treatment, suspension concentrates (flowables), ultra-low volume (ULV) liquids for microspraying, ultra-low volume (ULV) suspensions for microspraying, wettable granules or water-dispersible tablets, wettable powders for slurry treatment, water-soluble granules or water-soluble tablets, water-soluble powders for seed treatment, and wettable powders.

[0039] The formulation can typically be a liquid or solid carrier and one or more conventional formulation aids which can optionally be solid or liquid aids, such as non-epoxidized or epoxidized vegetable oils (e.g., epoxidized coconut oil, rapeseed oil or soybean oil), defoamers such as silicone oils, preservatives, clays, inorganic compounds, viscosity regulators, surfactants, binders and / or tackifiers. This composition can contain not only a combination of the compound of the present invention with one or more other biologically active substances such as fungicides, fungicides, anti-nematodes, plant activators, acaricides and insecticides, but can also further contain fertilizers, micronutrient donors or other preparations that affect the growth of banana plants.

[0040] This composition is prepared in a manner known per se, for example, in the absence of aids by grinding, sieving, and / or compressing the solid compound of the present invention, and in the presence of at least one aid, for example, by homogeneously mixing and / or grinding the compound of the present invention with one or more aids. In the case of the solid compound of the present invention, the grinding / milling of the compound is carried out to ensure a specific particle size.

[0041] Examples of compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil-dispersible directly sprayable or dilutable liquids, spreadable pastes, diluted emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulates in polymeric substances, which - at least - contain a compound according to any one of embodiments 1 to 13, and the type of composition should be selected according to the intended purpose and the circumstances at that time.

[0042] Generally, the composition contains 0.1 to 99%, in particular 0.1 to 95%, of a compound according to any one of embodiments 1 to 13 and 1 to 99.9%, in particular 5 to 99.9%, of at least one solid or liquid carrier, and usually 0 to 25%, in particular 0.1 to 20%, of the composition can be a surfactant (% means weight percent in any case). Concentrated compositions tend to be preferred for commercial products, but the end consumer usually uses diluted compositions with a fairly low concentration of the active ingredient.

[0043] Examples of foliar formulation types for premix compositions are as follows: GR: Granules WP: Wettable powders WG: Water-dispersible granules (powders) SG: Water-soluble granules SL: Soluble concentrates EC: Emulsifiable concentrates EW: Oil-in-water emulsions ME: Microemulsions SC: Aqueous suspension concentrates CS: Aqueous capsule suspensions OD: Oil-based suspension concentrates, and SE: Aqueous suspo-emulsions.

[0044] On the other hand, examples of seed treatment formulation types for premix compositions are as follows: WS: Wettable powders for seed treatment slurries LS: Liquids for seed treatment ES: Emulsions for seed treatment FS: Suspension concentrate for seed treatment WG: Wettable granules, and CS: Aqueous capsule suspension.

[0045] Examples of formulation types suitable for tank mix compositions are solutions, dilute emulsions, suspensions or mixtures thereof and dusts.

[0046] Similar to the nature of the formulation, application methods such as foliar application, irrigation, spraying, atomization, spreading, diffusion, coating or pouring are selected according to the intended purpose and the circumstances at that time.

[0047] Tank mix compositions are generally prepared by diluting one or more premix compositions containing different pest control agents and optionally further adjuvants with a solvent (e.g., water).

[0048] Suitable carriers and adjuvants can be solid or liquid and are substances commonly used in formulation technologies, such as natural or recycled mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.

[0049] Generally, tank mix formulations for foliar application 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 adjuvant can be a surfactant in an amount of 0 - 20%, particularly 0.1 - 15% based on the tank mix formulation.

[0050] 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 adjuvant can be a surfactant in an amount of 0 - 50%, particularly 0.5 - 40% based on the premix formulation.

[0051] Typically, a tank mix formulation for seed treatment application comprises from 0.25 to 80%, especially from 1 to 75%, of the desired component and from 99.75 to 20%, especially from 99 to 25%, of a solid or liquid adjuvant (including a solvent such as water), and the adjuvant can be a surfactant in an amount of from 0 to 40%, especially from 0.5 to 30%, based on the tank mix formulation.

[0052] Typically, a premix formulation for seed treatment application comprises from 0.5 to 99.9%, especially from 1 to 95%, of the desired component and from 99.5 to 0.1%, especially from 99 to 5%, of a solid or liquid auxiliary agent (including a solvent such as water), and the auxiliary agent can be a surfactant in an amount of from 0 to 50%, especially from 0.5 to 40%, based on the premix formulation.

[0053] Commercially available products will preferably be formulated as concentrates (e.g., premix compositions (formulations)), but the end user will typically use a diluted formulation (e.g., a tank mix composition).

[0054] A preferred seed treatment premix formulation is an aqueous suspension concentrate. This formulation can be applied to seeds using conventional treatment techniques and machinery such as fluidized bed technology, roller mill methods, rotostatic seed treaters, and drum coaters. Other methods such as jet fluidized beds may also be useful. The seeds can be pre-classified before application. After application, the 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.

[0055] Generally, the premix composition of the present invention contains from 0.5 to 99.9, especially from 1 to 95, advantageously from 1 to 50% by weight of the desired component and from 99.5 to 0.1, especially from 99 to 5% by weight of a solid or liquid auxiliary agent (including a solvent such as water), and the auxiliary agent (or auxiliary agent) can be a surfactant in an amount of from 0 to 50, especially from 0.5 to 40% by weight, based on the weight of the premix formulation.

[0056] Here, the present invention is illustrated by the following non-limiting examples. All cited documents are incorporated by reference.

Example

[0057] Biological Example Effect of various irrigation treatments of banana plants against black Sigatoka caused by the fungus Pseudocercospora fijiensis A banana greenhouse test was carried out in Wageningen, the Netherlands, to evaluate the effectiveness of various compounds against black Sigatoka in bananas. Tissue culture banana plantlets were transferred upon arrival to small pots (5×5 cm) filled with standard soil and acclimated by maintaining them at 28±2 °C and approximately 100% relative humidity (RH) for 2 weeks. Thereafter, the relative humidity was reduced to approximately 90%. A strain of Pseudocercospora fijiensis was collected and cultured on PDA medium. After 3 weeks, the mycelial colonies were fragmented and the fragments were sown on PDA and grown for approximately 4 - 6 weeks. Thereafter, mycelial colony pieces from the P. fijiensis strain were mixed with distilled water. The mycelial fragments were filtered through miracloth and the suspension was diluted to a final concentration of approximately 5×10 5 mycelial fragments / ml. This solution was incubated overnight at 27 °C to allow recovery from mixing. The next day, this inoculation mixture was "sprayed" onto both sides of the last fully expanded leaf of each "Cavendish" banana plant (cultivar Grand Naine) using a plant spray until runoff. The leaf was covered with a plastic bag for 3 days to ensure maximum humidity. Thereafter, the bag was removed and the plant was maintained in the greenhouse.

[0058] The compounds were each applied at a final concentration of 200 g AI / ha (calculated at a plant density of 1500 plants per ha). The application was carried out by irrigating 200 ml of water per plant. The plants were placed in small trays so that the applied compounds did not move between plants. The symptoms of the plants were monitored for 12 weeks after the last inoculation. The disease severity was visually evaluated based on whether the plants were dry or alive, the black Sigatoka spots and their size. This was converted to a number with a minimum of 1 (no infection observed) and a maximum of 9 (dry, highly infected, large spots).

[0059]

Table 2

[0060] Evaluation:

[0061]

Table 3

[0062] Conclusion: From these results, it was shown that the application of Compound 1 by irrigation significantly suppressed the severity of black Sigatoka development, and this application may be a promising alternative for combating black Sigatoka in banana plants.

Claims

1. A method for controlling or preventing damage to banana plants by phytopathogenic microorganisms of the genus Pseudocercospora, which comprises applying to the crop, locus or propagation material of banana plants a compound of formula (I): 【Chemical 1】 wherein Y is O, C=O or CR12R13; A is a 5- or 6-membered aromatic heterocyclic ring or a phenyl ring containing 1 to 3 heteroatoms independently selected from oxygen, nitrogen and sulfur, said aromatic heterocyclic ring or said phenyl being optionally substituted by one or more R6; R6, independently of one another, is halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-haloalkylthio, C1-C4-alkoxy-C1-4-alkyl or C1-C4-haloalkoxy-C1-C4-alkyl; R1, R2, R3, R4, R12 and R13, independently of one another, are hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl; R5 is hydrogen, methoxy or hydroxyl; B is phenyl substituted by one or more R8; R8, independently of one another, is halogen, cyano or the group -L-R9, where each L, independently of one another, is 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, where benzyl and phenyl are unsubstituted or substituted by halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl; R9 is, 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 R10 or heteroaryl which is unsubstituted or substituted by one or more R10, R10 is, 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), A compound according to or a salt or N-oxide thereof, wherein B and A-CO-NR5 are cis to each other on the 4-membered ring, a method comprising the step of administering a compound or a salt or N-oxide thereof or a tautomer or stereoisomer of said compound. Claim 2 The method according to claim 1, wherein the phytopathogenic microorganism is Pseudocercospora fujensis. Claim 3 Y is O or CH2, A is a 6-membered aromatic heterocyclic ring containing 1 to 2 nitrogen atoms or a phenyl ring, and the aromatic heterocyclic ring or the phenyl ring may be optionally substituted with one or more R6, R6 is, independently of one another, 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 with one or more R8, R8 is, independently of one another, selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, and C3-C6-cycloalkyl, The method according to claim 1 or 2. Claim 4 The method according to any one of claims 1 to 3, wherein A is a 6-membered aromatic heterocycle containing 1 to 2 nitrogen atoms and having 1 to 3 substituents selected from R6, or a phenyl ring having 1 or 3 substituents selected from R6.

5. The method according to any one of claims 1 to 4, wherein B is phenyl substituted by 1 to 3 substituents R8.

6. B is phenyl substituted by 1 to 3 substituents independently selected from fluoro, chloro, trifluoromethyl, cyclopropyl, difluoromethoxy and trifluoromethoxy, A is phenyl, pyridyl, or pyrazinyl, and these rings are, independently of each other, unsubstituted or substituted by 1 to 3 substituents independently selected from chloro, bromo, fluoro, methyl, cyano and trifluoromethyl, Y is O or CH2, R1, R2, R3, R4, and R5 are each hydrogen, The method according to any one of claims 1 to 5.

7. Y is CH2, B is mono- or di-halogen-substituted phenyl, A is selected from phenyl, pyrazinyl and pyridyl, and each of these is mono- or di-substituted by a substituent independently selected from halogen and C1-C4-haloalkyl, R1, R2, R3, R4 and R5 are each hydrogen, The method according to any one of claims 1 to 6.

8. The compound is of formula (Ic) 【Chemical 2】 (wherein, R11 and R12 are independently selected from halogen, A is pyridyl substituted by one or two substituents independently selected from halogen and C 1 ~C 4 -haloalkyl) The method according to any one of claims 1 to 7, which is a compound.

9. R11 and R12 are independently selected from chloro and fluoro, A is one or two C 1 ~C 4 -pyrid-2-yl or pyrid-3-yl substituted by a haloalkyl substituent, The method according to claim 7.

10. A is 【Chemical Formula 3】 selected from R13 is C 1 ~C 4 -haloalkyl, the method according to any one of claims 1 to 9.

11. The compound is of formula (Ic) 【Chemical 4】 (wherein R11, R12, and A are as defined in the following table: 【Table 1】 as shown therein) The method according to claim 1, which is selected from any one of compounds 1 to 7.

12. The method according to any one of claims 1 to 11, which comprises perfusion administration of the compound according to any one of claims 1 to 11.

13. A method for cultivating banana plants, which comprises applying the compound according to any one of claims 1 to 11 to banana plants or their propagation materials, or treating the banana plants or their propagation materials with the compound.

14. Use of a compound according to any one of claims 1 to 11 for controlling or preventing damage to banana plants caused by the phytopathogenic microorganism Pseudocercospora fijiensis.

15. The use according to claim 14, wherein the use of the compound according to any one of claims 1 to 11 is a perfusion application.

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