Methods for controlling or preventing plant damage caused by plant pathogenic microorganisms of the genus Macrohomina

Abstract

The present invention relates to a method for controlling or preventing damage to plants caused by plant pathogenic microorganisms of the genus Macrohomina, comprising administering to a plant a compound of formula (I) [Formula 1] The present invention relates to a method comprising applying a compound according to the formula: TIFF2023506165000022.tif46157 (wherein R1, R2, R3, R4, R5, Y, A, B are as defined herein) to a plant crop, a locus thereof, or propagation material thereof.

Description

[Technical Field]

[0001] The present invention relates to a method for controlling or preventing plant damage caused by phytopathogenic microorganisms of the genus Macrohomina. [Background technology]

[0002] Macrohomina species are fungi that infect nearly 500 plant species in over 100 families.

[0003] The pathogen affects the vascular system of the roots and basal internodes of its host, blocking the transport of water and nutrients to the upper part of the plant. As a result, progressive wilting, premature blight, loss of vigor, and reduced yield are characteristic symptoms of this infection. The fungus also causes many diseases such as damping-off, seedling blight, neck rot, stem rot, charcoal rot, basal stem rot, and root rot. Summary of the Invention [Means for solving the problem]

[0004] The present invention provides further improved methods for controlling or preventing plant damage caused by phytopathogenic microorganisms of the genus Macrohomina. DETAILED DESCRIPTION OF THE INVENTION

[0005] Cyclobutylcarboxamide compounds and methods for their preparation are disclosed in WO 2013 / 143811 and WO 2015 / 003951. It has now surprisingly been found that certain cyclobutylcarboxamide compounds disclosed in WO 2013 / 143811 and / or WO 2015 / 003951 are highly effective in controlling or preventing plant damage caused by phytopathogenic microorganisms of the genus Macrohomina. As such, these highly effective compounds represent an important new solution for farmers to control or prevent plant damage caused by phytopathogenic microorganisms of the genus Macrohomina.

[0006] Thus, in embodiment 1, there is provided a method for controlling or preventing plant damage caused by plant pathogenic microorganisms of the genus Macrohomina, comprising administering to a plant crop, its locus or its propagation material a compound of formula (I) [ka] (In the formula, Y is O, C=O or CR12R13; A is a 5- or 6-membered aromatic heterocycle or a phenyl ring containing 1 to 3 heteroatoms each independently selected from oxygen, nitrogen, and sulfur, wherein the aromatic heterocycle or phenyl is optionally substituted with one or more R6; R6 are, independently of one another, 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 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 by one or more R8; R8 are, independently of one another, halogen, cyano or a group -L-R9, where each L is, independently of one another, 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 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 R10 or heteroaryl which is unsubstituted or substituted by one or more R10, 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. or a salt or N-oxide thereof, A method is provided that includes applying a compound, or a salt or N-oxide thereof, or a tautomer or stereoisomer of these compounds, wherein B and A-CO-NR5 are cis to each other on the four-membered ring.

[0007] A more preferred method according to embodiment 1 is shown in the following embodiment.

[0008] 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 optionally being substituted with one or more R6; R6 are, 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 by one or more R8; 2. The method of 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.

[0009] In embodiment 3, there is provided the method of embodiment 1 or embodiment 2, 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.

[0010] 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.

[0011] 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 with one to three substituents independently selected from chloro, bromo, fluoro, methyl, cyano, and trifluoromethyl; Y is O or CH; and R, R, R, R, and R are each hydrogen.

[0012] 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.

[0013] The compounds of formula (I) disclosed in any one of embodiments 1-6 may be cis racemates, in which the left phenyl ring and the right AC(=O)-NH group are cis to each other on the cyclobutyl ring: [ka] Represents.

[0014] Thus, a racemic compound of formula (I) is a 1:1 mixture of compounds of formulas (Ia) and (Ib). The wedge-shaped 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 the racemic compound.

[0015] It has also been surprisingly found that one enantiomer of the compound of formula (I) is particularly useful for controlling or preventing damage to plants by phytopathogenic microorganisms of the species of the genus Macrohomina.

[0016] Thus, in embodiment 7, the compound has the formula (Ia) [ka] The method of any one of embodiments 1 to 6 is provided, wherein

[0017] Those skilled in the art will recognize that, according to the method described in embodiment 2, the compound of formula (Ia) is generally applied as part of a pesticidal composition. Accordingly, embodiment 8 provides a method for controlling or preventing plant damage caused by phytopathogenic microorganisms of the genus Macrohomina, comprising applying to a plant crop, its locus, or its propagation material a pesticidal composition comprising a compound of formula (Ia) and one or more formulation adjuvants. embodiment 9 provides a method for controlling or preventing plant damage caused by phytopathogenic microorganisms of the genus Macrohomina, comprising applying to a plant crop, its locus, or its propagation material a pesticidal composition comprising a compound of formula (Ia) and one or more formulation adjuvants. In the method described in embodiment 9, in a 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, in particular greater than 4:1, advantageously greater than 9:1, desirably greater than 20:1, in particular greater than 35:1.

[0018] 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.

[0019] Preferably, in a composition comprising a compound of formula (Ia), its trans isomer (i.e., in which the B and A-CO-NR groups are trans relative to each other) and a compound of formula (Ib), the composition comprises the compound of formula (Ia) in a concentration of at least 50%, more preferably 70%, even more preferably 85%, particularly more than 90%, and 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.

[0020] Furthermore, as a tenth embodiment, there is provided a method for controlling or preventing damage to plants caused by plant pathogenic microorganisms of the genus Macrohomina, comprising administering to a plant crop, its locus or its propagation material a compound of formula (Ic): [ka] (In the formula, R11 and R12 are independently selected from halogen; A is pyridyl substituted by one or two substituents independently selected from halogen and C1-C4-haloalkyl. The present invention provides a method comprising applying a compound according to the method of the present invention.

[0021] As an eleventh embodiment, R11 and R12 are independently selected from chloro and fluoro; The method of embodiment 10 is provided, wherein A is pyrid-2-yl or pyrid-3-yl substituted by one or two C1-C4-haloalkyl substituents.

[0022] As a twelfth embodiment, A is, [ka] is selected from The method according to embodiment 10 or 11 is provided, wherein R13 is C1-C4-haloalkyl, preferably trifluoromethyl.

[0023] In embodiment 13, the compound has formula (Ic): [ka] wherein R11, R12 and A are as defined in the table below.

[0024] [Table 1]

[0025] As a fourteenth embodiment, - providing a composition comprising a compound according to any one of embodiments 1 to 13; - applying the composition to the propagation material; - planting the propagation material; The method according to any one of embodiments 1 to 13 is provided, comprising:

[0026] As a fifteenth embodiment, - providing a composition comprising a compound according to any one of embodiments 1 to 13; - applying the composition to the plant crop or to the locus thereof; The method according to any one of embodiments 1 to 13 is provided, comprising:

[0027] As embodiment 16, there is provided the use of a compound according to any one of embodiments 1 to 13 for controlling or preventing damage to plants caused by plant pathogenic microorganisms of the species Macrohomina.

[0028] In 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 plants caused by phytopathogenic microorganisms of the genus Macrohomina, in particular Macrohomina phaseolina or Macrohomina limbalis, more particularly Macrohomina phaseolina.

[0029] As an eighteenth embodiment, Embodiment 1 A method of cultivating strawberry plants is provided, comprising applying to strawberries or their propagation material or treating the strawberries or their propagation material with a compound according to any one of claims 1 to 13.

[0030] In embodiment 19, the plant comprises: Abelmoschus Abies Abutilon Acer Allium Amaranthus Ambosia Antirrhinum Dogbane (Apocynum) Arachis Arrhenatherum Milkweed (Asclepias) Asparagus Avena Begonia Beat (Beta) Bidens Bouteloua Brassica Campanula Canjanus Cannabis Capsicum Cassia Catalpa Celosia Cypress (Chamaecyparis) Chenopodium Chrysanthemum Chickpea (Cicer) Thistle (Cirsium) Watermelon genus (Citrullus) Citrus Conyza genus Cornus Crotalaria Cucumis Cucurbita Cupressus Cyamopsis Dahlia Datura Dichondra Elymus Artemisia genus (Erigeron) Eryngium Eupatorium Euphorbia Buckwheat (Fagopyrum) Strawberry Glycine Gossypium Ivy (Hedera) Sunflower (Helianthus) Hibiscus Sweet potato genus (Ipomoea) Juniperus Koelreuteria Kummerowia Lactuca Genus Lespedeza Ligustrum Lilium Lotus Lupinus Tomato genus (Lycopersicon) Malva Medicago Melilotus Muhlenbergia Nicandra Nicotiana Nyssa Oenothera Opuntia Parthenium Phaseolus Phlox Picea pine (Pinus) Pisum Polygonum Cherry genus (Prunus) Pseudotsuga Pueraria Pyracantha genus Quercus Rhododendron Castor bean (Ricinus) Robinia Roystonea palms Rudbeckia genus Salvia Santolina Schefflera Senna genus Sequoia genus (Sequoiadendron) Sesamum Sesbania Setaria Fern genus (Sida) Solanum Goldenrod (Solidago) Sorghum Strophostyles Sugarbeet Genus Tagetes Thuja Trifolium genus Tristania Verbena Vicia Vigna Vitis Genus Zea, and Zinnia The method or use according to any one of embodiments 1 to 17 is provided, wherein the method or use is selected from the group consisting of:

[0031] As embodiment 20, there is provided a method or use according to any one of embodiments 1 to 18, wherein the plant is selected from peanut, cabbage, pepper, chickpea, soybean, sunflower, sweet potato, sugar beet, alfalfa, sesame, potato, sorghum, wheat, maize, and strawberry.

[0032] In embodiment 21, the plant is a strawberry and the plant pathogenic microorganism is Macrohomina phaseolina. Embodiment The method according to any one of claims 1 to 20 is provided.

[0033] The preparation of the compounds defined in the methods described in any one of embodiments 1 to 13 is disclosed in WO 2013 / 143811 and WO 2015 / 003951, which are incorporated herein by reference.

[0034] Definition: The term "halogen" denotes fluoro, chloro, bromo or iodo, in particular fluoro, chloro or bromo.

[0035] The term "alkyl" or "alk" as used herein, alone or as part of a larger group (such as alkoxy, alkylthio, alkoxycarbonyl, and alkylcarbonyl), is straight-chain 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 C1-C4 alkyl group.

[0036] As used herein, "haloalkyl" refers to an alkyl group as defined above that is substituted with one or more of the same or different halogen atoms, such as CF, CFCl, CFH, CClH, FCH, ClCH, BrCH, CHCHF, (CH)CF, CFCH, or CHFCH.

[0037] The methods and uses according to any one of embodiments 1 to 18 are preferably for controlling or preventing crop damage caused by plant pathogenic microorganisms that are resistant to other fungicides. A Cercospora fungus that is "resistant" to a particular fungicide refers to, for example, a strain of Cercospora fungus that is less susceptible to that fungicide compared to the expected susceptibility of the same species of Cercospora fungus. The expected susceptibility can be determined, for example, using a strain that has not previously been exposed to the fungicide.

[0038] The application according to any one of the methods or uses of embodiments 1 to 18 is preferably to a plant crop, a locus thereof or a propagation material thereof. Preferably, the application is to a plant crop or a propagation material thereof, more preferably to a propagation material. The application of the compound of the present invention can be carried out according to any of the usual application forms, such as foliar application, drench, soil application, furrow application, etc.

[0039] The compounds as defined in any one of embodiments 1 to 13 are preferably used for pest control at 1 to 500 g / ha, preferably 10 to 70 g / ha.

[0040] The compounds of any one of embodiments 1-13 are suitable for use on any peanut 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.

[0041] 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 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) gases, 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 dusts, liquids for seed treatment, suspension concentrates (flowables), liquids for ultra low volume application (ulv), suspensions for ultra low volume application (ulv), water dispersible granules or water dispersible tablets, wettable powders for slurry treatment, water-soluble granules or tablets, water-soluble dusts and wettable powders for seed treatment.

[0042] 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, nematicides, plant activators, acaricides, and insecticides, but may also comprise fertilizers, micronutrient donors, or other preparations that affect plant growth.

[0043] 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 and / or grinding the compound with one or more auxiliaries, In the case of the solid compound of the invention, grinding / milling of the compound is carried out to ensure a specific particle size.

[0044] 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 embodiments 1 to 13, the type of composition being chosen depending on the intended purpose and the circumstances at hand.

[0045] Typically, the composition comprises 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 typically 0 to 25%, in particular 0.1 to 20%, of the composition can be surfactants (% means percent by weight in each case). While concentrated compositions tend to be preferred in commercial products, end users usually use diluted compositions with a much lower concentration of active ingredient.

[0046] Examples of foliar formulation types for premix compositions are as follows: GR: Granules WP: Wettable powder 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.

[0047] 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: Emulsifiable concentrate for seed treatment FS: Suspension concentrate for seed treatment WG: water dispersible granules, and CS: Aqueous capsule suspension.

[0048] Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions or mixtures thereof, and dusts.

[0049] The nature of the formulation as well as the method of application, whether foliar application, dredging, spraying, atomizing, dusting, spreading, painting or pouring, will be selected according to the intended purpose and the circumstances at hand.

[0050] Tank-mix compositions are generally prepared by diluting with a solvent (eg, water) one or more pre-mix compositions containing different pesticides and, optionally, additional adjuvants.

[0051] Suitable carriers and adjuvants may be solid or liquid and are substances commonly used in formulation technology, such as natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.

[0052] Generally, tank-mix formulations for foliar or soil application comprise 0.1 to 20%, especially 0.1 to 15%, of the desired ingredient and 99.9 to 80%, especially 99.9 to 85%, of a solid or liquid adjuvant (including, for example, a solvent such as water), which may be a surfactant in an amount of 0 to 20%, especially 0.1 to 15%, based on the tank-mix formulation.

[0053] Typically, premix formulations for foliar application comprise 0.1 to 99.9%, in particular 1 to 95%, of the desired ingredient and 99.9 to 0.1%, in particular 99 to 5%, of a solid or liquid adjuvant (including, for example, a solvent such as water), which may be a surfactant in an amount of 0 to 50%, in particular 0.5 to 40%, based on the premix formulation.

[0054] Typically, tank-mix formulations for seed treatment application comprise 0.25 to 80%, especially 1 to 75%, of the desired ingredient and 99.75 to 20%, especially 99 to 25%, of a solid or liquid adjuvant (including, for example, a solvent such as water), which may be a surfactant in an amount of 0 to 40%, especially 0.5 to 30%, based on the tank-mix formulation.

[0055] Typically, premix formulations for seed treatment application comprise 0.5 to 99.9%, especially 1 to 95%, of the desired component and 99.5 to 0.1%, especially 99 to 5%, of a solid or liquid adjuvant (including, for example, a solvent such as water), which may be a surfactant in an amount of 0 to 50%, especially 0.5 to 40%, based on the premix formulation.

[0056] Commercially available products will preferably be formulated as concentrates (e.g., premix compositions), while end users will typically employ dilute formulations (e.g., tank-mix compositions).

[0057] The preferred seed treatment premix formulation is an aqueous suspension concentrate.This formulation can be applied to seeds using conventional treatment techniques and machines, such as fluidized bed technology, roller mill method, rotostatic seed treatment machine 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.This procedure is known in the art.The compound of the present invention is particularly suitable for use in soil and seed treatment applications.

[0058] Generally, the premix compositions of the present invention contain 0.5 to 99.9, especially 1 to 95, advantageously 1 to 50% by weight of the desired component and 99.5 to 0.1, especially 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, especially 0.5 to 40% by weight, based on the weight of the premix formulation.

[0059] Further provided is a method for controlling or preventing damage to strawberry plants by a plant pathogenic microorganism selected from BOTRYTIS CINEREA and PODOSPHAERA MACULARIS, the method comprising applying a compound according to any one of embodiments 1 to 13 to the plant crop, its locus, or its propagation material.

[0060] The invention will now be illustrated by the following non-limiting examples, all citations of which are incorporated by reference. [Example]

[0061] Biological Examples Effect of various fungicide treatments on Macrohomina species A strawberry pot trial was performed in a greenhouse in Vero Beach, USA to evaluate the efficacy of various compounds against Macrohomina phaseolina.

[0062] Plants were planted in 4 L pots filled with Vero Beach Mix (50% potting medium and 50% pasteurized sand). The plants were bare-root strawberries of the variety "Sweet Ann." The strawberry plants were partially planted and then inoculated with 2 grams of infested millet. The inoculum was propagated on twice-sterilized millet for 1-2 weeks. The isolate used was originally isolated from strawberry. After inoculation, the roots were completely covered. On the day of planting, each plant was drench-applied with 100 mL of compound solution. Application rates were calculated based on a planting distance of 30.5 cm x 45.7 cm. The plants were grown in a greenhouse with an average daytime temperature of 32°C and a nighttime temperature of 21°C. The plants were watered daily. Disease severity was assessed 44 and 65 days after application using an IS 0-5 index scale (5 = severe damage, 0 = no damage).

[0063] [Table 2]

[0064] [Table 3]

[0065] [Table 4]

[0066] [Table 5]

[0067] [Table 6]

[0068] [Table 7]

[0069] [Table 8]

[0070] [Table 9]

[0071] Conclusion: In this study, compound 1 showed excellent activity against Macrophomina phaseolina in strawberries over a sustained period of 65 days after application. Compound 2 showed moderate activity (44%) up to 44 days, after which it lost activity almost completely.

Claims

1. 1. A method for controlling or preventing damage to plants caused by plant pathogenic microorganisms of the genus Macrophomina, comprising administering to a plant crop, its locus or its propagation material a compound of formula (I) 【Chemical 1】 (In the formula, Y is O, C=O or CR12R13; A is a 5- or 6-membered aromatic heterocycle or a phenyl ring containing 1 to 3 heteroatoms each independently selected from oxygen, nitrogen, and sulfur, wherein the aromatic heterocycle or the phenyl is optionally substituted with one or more R6; R6 are, independently of one another, 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 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 by one or more R8; R8 are independently selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, and C3-C6-cycloalkyl. wherein B and A-CO-NR5 are cis to each other on the four-membered ring, or a composition comprising a tautomer of these compounds.

2. Y is O or CH2; A is a 6-membered aromatic heterocycle containing 1 to 2 nitrogen atoms or a phenyl ring, said aromatic heterocycle or said phenyl optionally being substituted with one or more R6; R6 are, 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 are independently selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy and C3-C6-cycloalkyl; The method of claim 1.

3. 3. The method according to claim 1, 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.

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

5. 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, which rings are, independently of one another, unsubstituted or substituted with one to three 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 4.

6. 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 with substituents independently selected from halogen and C1-C4-haloalkyl; 6. The method of any one of claims 1 to 5, wherein R1, R2, R3, R4 and R5 are each hydrogen.

7. The compound has the formula (Ic) 【Chemistry 2】 (In the formula, R11 and R12 are independently selected from halogen; A is a halogen and C 1 ~C 4 -pyridyl substituted by 1 or 2 substituents independently selected from -haloalkyl The method according to any one of claims 1 to 6, wherein the compound is

8. R11 and R12 are independently selected from chloro and fluoro; A is one or two Cs 1 ~C 4 -pyrid-2-yl or pyrid-3-yl substituted by haloalkyl substituents; The method of claim 7.

9. A is, 【Chemistry 3】 is selected from R13 is C 1 ~C 4 The method of any one of claims 1 to 3, wherein the alkyl group is -haloalkyl.

10. The compound has the formula (Ic) 【Chemistry 4】 (wherein R11, R12, and A are as shown in the table below: 【Table 1】 (as defined in The method of claim 1, wherein the compound is selected from any one of compounds 1 to 7.

11. The method according to any one of claims 1 to 10, wherein the plant pathogenic microorganism is Macrophomina phaseolina or Macrophomina limbalis.

12. The plant is Abelmoschus Abies Abutilon Acer Allium Amaranthus Ragweed (Ambosia) Antirrhinum Dogbane (Apocynum) Arachis Arrhenatherum Milkweed (Asclepias) Asparagus Avena Begonia Beat (Beta) Bidens Bouteloua Brassica Campanula Canjanus Cannabis Capsicum Cassia genus Catalpa Celosia Cypress (Chamaecyparis) Chenopodium Chrysanthemum Chickpea (Cicer) Thistle (Cirsium) Watermelon genus (Citrullus) Citrus Conyza genus Cornus Crotalaria Cucumis Cucurbita Cypress genus (Cupressus) Cyamopsis Dahlia genus Datura Dichondra Elymus Erigeron Eryngium Eupatorium Euphorbia Buckwheat (Fagopyrum) Strawberry Glycine Gossypium Ivy (Hedera) Sunflower genus (Helianthus) Hibiscus Sweet potato genus (Ipomoea) Juniperus Koelreuteria Kummerowia Lactuca genus Lespedeza Ligustrum Lily genus (Lilium) Lotus genus Lupinus Tomato genus (Lycopersicon) Malva genus Medicago Melilotus Muhlenbergia Genus Nicandra Nicotiana Nyssa Oenothera Opuntia Parthenium Phaseolus Phlox Picea Pine genus (Pinus) Pisum Polygonum Cherry genus (Prunus) Pseudotsuga Pueraria Pyracantha genus Oak (Quercus) Rhododendron Castor bean (Ricinus) Robinia Roystonea Rudbeckia genus Salvia Santolina Schefflera Senna genus Sequoia genus (Sequoiadendron) Sesamum Sesbania Setaria Fern genus (Sida) Solanum Goldenrod (Solidago) Sorghum Strophostyles Sugarbeet Tagetes Thuja Trifolium genus Tristania Verbena Vicia Vigna Vitis Genus Zea (Zea), and Zinnia genus The method according to any one of claims 1 to 11, wherein the compound is selected from the group consisting of:

13. 13. The method of any one of claims 1 to 12, wherein the plant is selected from peanut, cabbage, pepper, chickpea, soybean, sunflower, sweet potato, sugar beet, alfalfa, sesame, potato, sorghum, wheat, maize, and strawberry.

14. 14. The method according to any one of claims 1 to 13, wherein the plant is strawberry and the plant pathogenic microorganism is macrophomina phaseolina.

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