Method for controlling or preventing infestation of cereal plants by phytopathogenic microorganism fusarium pseudograminearum

Abstract

The present invention relates to a method for controlling or preventing infestation of cereal plants by the phytopathogenic microorganism Fusarium pseudograminearum, said method comprising applying to a plant crop, its locus or its seed a compound according to formula (I) wherein R1, R2, R3, R4, R5, Y, A, B are as defined herein. # imgabs0 #

Description

[0001] This application is a divisional application of Chinese Patent Application No. 201980060460.4 with the invention title of "Method for Controlling or Preventing Cereal Plants from Being Infected by the Phytopathogenic Microorganism Fusarium pseudograminearum", the filing date of which is September 16, 2019, and the priority date of which is September 19, 2018. Technical Field

[0002] The present invention relates to a method for controlling or preventing cereal plants from being infected by the phytopathogenic microorganism Fusarium pseudograminearum. Background Art

[0003] Crown rot is one of the most yield-robbing diseases in wheat. Crown rot is mainly caused by the phytopathogenic fungus Fusarium pseudograminearum. Across the United States, the average loss of winter wheat caused by crown rot in large areas throughout the Pacific Northwest is estimated to be as high as 9.5%, and similar losses have been seen in other western states of the United States. Outside of North America, crown rot is also a disease of particular concern in Australia. Over the past three decades, crown rot has become a disease of the most relative importance in the northern Australian grain production regions. Experts believe that the recent surge in the prevalence of crown rot in Australia is due to cereals being grown in closer rotations and the practice of leaving stubble becoming more common. In addition, in seasons when environmental conditions permit, crown rot can reduce wheat yields by up to 100% in Australia and up to 65% in North America.

[0004] Therefore, there is a continuing need to find improved methods for treating diseases associated with the phytopathogenic fungus Fusarium pseudograminearum. Accordingly, the present invention provides additional methods for controlling or preventing cereal plants from being infected by the phytopathogenic microorganism Fusarium pseudograminearum. Detailed Description

[0005] Cyclobutylformamide compounds and methods for their preparation have been disclosed in WO 2013 / 143811 and WO 2015 / 003951. It has now unexpectedly been found that certain cyclobutylformamide compounds disclosed in WO 2013 / 143811 and / or WO 2015 / 003951 are very effective in controlling or preventing cereal plants from being infected by the phytopathogenic microorganism Fusarium pseudograminearum. Accordingly, these very effective compounds provide important new solutions for farmers to control or prevent diseases of cereal plants, especially wheat and barley, and more particularly crown rot disease in wheat.

[0006] Accordingly, as in Example 1, there is provided a method for controlling or preventing cereal plants from being infected by the phytopathogenic microorganism *Fusarium pseudograminearum*, the method comprising applying a compound according to formula (I) to a plant crop, its locus or its seeds

[0007]

[0008] wherein

[0009] Y is O, C═O or CR12R13;

[0010] A is a 5- or 6-membered heteroaromatic ring or a benzene ring, the heteroaromatic ring containing 1 to 3 heteroatoms each independently selected from oxygen, nitrogen and sulfur; the heteroaromatic ring or the phenyl group is optionally substituted by one or more R6;

[0011] R6 are each independently halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-halosulfanyl, C1-C4-alkoxy-C1-4-alkyl, or C1-C4-haloalkoxy-C1-C4-alkyl;

[0012] R1, R2, R3, R4, R12 and R13 are each independently hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl,

[0013] R5 is hydrogen, methoxy or hydroxy,

[0014] B is a phenyl group substituted by one or more R8,

[0015] R8 are each independently halogen, cyano or the group -L-R9, wherein each L is independently a bond, -O-, -OC(O)-, -NR7-, -NR7CO-, -NR7S(O)n-, -S(O)n-, -S(O)nNR7-, -COO- or CONR7-,

[0016] n is 0, 1 or 2,

[0017] R7 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, benzyl or phenyl, wherein benzyl and phenyl are unsubstituted or substituted by halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl,

[0018] R9 is, independently of one another, unsubstituted or substituted by one or more R10 C1-C6-alkyl, unsubstituted or substituted by one or more R10 C3-C6-cycloalkyl, unsubstituted or substituted by one or more R10 C6-C14-bicycloalkyl, unsubstituted or substituted by one or more R10 C2-C6-alkenyl, unsubstituted or substituted by one or more R10 C2-C6-alkynyl, unsubstituted or substituted by R10 phenyl, or unsubstituted or substituted by one or more R10 heteroaryl,

[0019] 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;

[0020] or a salt or N-oxide thereof;

[0021] wherein B and A-CO-NR5 are cis to each other on the four-membered ring,

[0022] or a tautomer or stereoisomer of these compounds.

[0023] In the following examples, more preferred methods according to Example 1 are given.

[0024] As in Example 2, there is provided a method according to Example 1, wherein

[0025] Y is O or CH2;

[0026] A is a 6-membered heteroaromatic ring or a benzene ring, the heteroaromatic ring containing 1 to 2 nitrogen atoms; the heteroaromatic ring or the phenyl is optionally substituted by one or more R6;

[0027] R6 is, independently of one another, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-haloalkoxy;

[0028] R1, R2, R3, R4 and R5 are each hydrogen;

[0029] B is a phenyl substituted by one or more R8;

[0030] R8 is, independently of one another, selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy and C3-C6-cycloalkyl.

[0031] As in Example 3, there is provided a method according to Example 1 or Example 2, wherein A is a 6-membered heteroaromatic ring or a benzene ring, the heteroaromatic ring contains 1 to 2 nitrogen atoms and has 1 to 3 substituents selected from R6, and the benzene ring has 1 or 3 substituents selected from R6.

[0032] As in Example 4, there is provided a method according to any one of Examples 1 to 3, wherein B is a phenyl group substituted with 1 to 3 substituents R8.

[0033] As in Example 5, there is provided a method according to any one of Examples 1 to 4, wherein B is a phenyl group substituted with 1 to 3 substituents, and the substituents are independently selected from fluorine, chlorine, trifluoromethyl, cyclopropyl, difluoromethoxy, and trifluoromethoxy;

[0034] A is phenyl, pyridyl, or pyrazinyl, the rings are each independently unsubstituted or substituted with 1 to 3 substituents independently selected from chlorine, bromine, fluorine, methyl, cyano, and trifluoromethyl, Y is O or CH2, and R1, R2, R3, R4, and R5 are each hydrogen.

[0035] As in Example 6, there is provided a method according to any one of Examples 1 to 5, wherein

[0036] Y is CH2;

[0037] B is a mono- or di-halogen-substituted phenyl group;

[0038] A is selected from phenyl, pyrazinyl, and pyridyl, and the phenyl, pyrazinyl, and pyridyl are each independently mono-substituted or di-substituted with a substituent selected from halogen and C1-C4-haloalkyl;

[0039] R1, R2, R3, R4, and R5 are each hydrogen.

[0040] The compound having formula (I) disclosed according to any one of Examples 1 to 6 represents a cis-racemate: the benzene ring on the left and the A-C(=O)-NH group on the right are cis to each other on the cyclobutyl ring:

[0041]

[0042] Therefore, the racemic compound having formula (I) is a 1:1 mixture of the compounds having formula (Ia) and (Ib). The wedge bonds shown in the compounds having formula (Ia) and (Ib) represent the absolute stereochemistry, while the thick straight bonds as shown for the compound having formula (I) represent the relative stereochemistry in the racemic compound.

[0043] It has also surprisingly been found that one enantiomer of the compounds of formula (I) is particularly useful for controlling or preventing infestation of cereal plants by the phytopathogenic microorganism Fusarium pseudograminearum.

[0044] Accordingly, as in Example 7, there is provided a method according to Example 1, wherein the compound has formula (Ia)

[0045]

[0046] As is known to the person skilled in the art, according to the method of Example 1, the compounds of formula (Ia) are generally applied as part of a pesticidal composition. Accordingly, as in Example 8, there is provided a method for controlling or preventing infestation of cereal plants by the phytopathogenic microorganism Fusarium pseudograminearum, which method comprises applying a pesticidal composition comprising a compound as defined in any one of Examples 1 - 7 and one or more formulation adjuvants to the plant crop, its locus or its seeds. As in Example 9, there is provided a method for controlling or preventing infestation of cereal plants by the phytopathogenic microorganism Fusarium pseudograminearum, which method comprises applying a pesticidal composition comprising a compound of formula (Ia) and one or more formulation adjuvants to the plant crop, its locus or its seeds. In the method according to Example 9, for 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 the compound of formula (Ia) to the compound 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, particularly greater than 35:1.

[0047] Mixtures are also understood to be part of the present invention, which mixtures contain up to 50%, preferably up to 40%, more preferably up to 30%, in particular up to 20%, advantageously up to 10%, desirably up to 5%, particularly up to 3% of the trans stereoisomer of the compound of formula (I) (i.e. in which the B and A - C(=O)-NH groups are trans to each other). 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, particularly greater than 35:1.

[0048] Preferably, in a composition comprising a compound of formula (Ia), its trans isomer (i.e., where the B and A-CO-NR2 groups are trans to each other) and a compound of formula (Ib), the composition comprises a compound of formula (Ia) at a concentration of at least 50%, more preferably 70%, even more preferably 85%, especially above 90%, and particularly preferably above 95%, each based on the total amount of the compound of formula (Ia), its trans isomer and the compound of formula (Ib).

[0049] Furthermore, as in Example 10, a method for controlling or preventing cereal plants from being infected by the phytopathogenic microorganism Fusarium pseudograminearum is provided, the method comprising applying a compound according to formula (Ic) to a plant crop, its locus or its seeds

[0050]

[0051] wherein

[0052] R11 and R12 are independently selected from halogen;

[0053] A is pyridyl, which is substituted by one or two substituents independently selected from halogen and C1-C4-haloalkyl.

[0054] As in Example 11, a method according to Example 10 is provided, wherein

[0055] R11 and R12 are independently selected from chlorine and fluorine;

[0056] A is pyridin-2-yl or pyridin-3-yl substituted by one or two C1-C4-haloalkyl substituents.

[0057] As in Example 12, a method according to Example 10 or 11 is provided, wherein

[0058] A is selected from

[0059]

[0060]

[0061] R13 is C1-C4-haloalkyl, preferably trifluoromethyl.

[0062] As in Example 13, a method according to any one of Examples 10 to 12 is provided, wherein the compound is selected from any one of Compounds 1 to 7 of formula (Ic)

[0063]

[0064] wherein R11, R12 and A are as defined in the following table:

[0065] Compound A R11 R12 1 2 - Trifluoromethyl - pyridin - 3 - yl Cl Cl 2 3 - Trifluoromethyl - pyridin - 2 - yl Cl Cl 3 3 - Trifluoromethyl - pyridin - 2 - yl F F 4 3 - Trifluoromethyl - pyridin - 2 - yl Cl F 5 3 - Chloro - pyridin - 2 - yl Cl Cl 6 2 - Methyl - pyridin - 3 - yl Cl Cl 7 2 - Trifluoromethyl - pyridin - 3 - yl Cl F

[0066] As in Example 14, there is provided a method according to any one of Examples 10 to 12, wherein the compound has formula (Ic)

[0067]

[0068] wherein R11, R12 and A are as defined in the following table:

[0069]

[0070]

[0071] The compound of Example 14, namely Compound 1, when used as a seed treatment agent for wheat seeds, has shown unexpectedly strong biological activity against Fusarium pseudograminearum. In particular, compared to a commercial seed treatment agent (see the biological examples section), Compound 1 not only shows a decrease in the amount of white heads, but also significantly increases the yield of wheat compared to the commercial treatment agent. In fact, when Compound 1 is applied as a seed treatment agent, the yield increase is more than twice that compared to other commercial treatment agents. This is unexpected because those skilled in the art know that the activity level of a class of compounds against a specific species of Fusarium (see the biological examples) cannot be predicted.

[0072] As in Example 15, there is provided a method according to any one of Examples 1 to 14, wherein the cereal plant is wheat or barley, especially wheat.

[0073] As in Example 16, there is provided a method according to any one of Examples 1 to 15, wherein the compound as defined in any one of Examples 1 to 14 is applied as a seed treatment agent. In particular, the preferred application rate to the seeds is in the range of 0.002 to 0.03 mg AI / seed.

[0074] As in Example 17, there is provided a method according to any one of Examples 1 to 16, the method comprising the steps of:

[0075] - providing a composition comprising the compound as defined in any one of Examples 1 to 14 (especially Compound 1);

[0076] - applying the composition to the seeds;

[0077] - planting the seeds.

[0078] As in Example 18, there is provided a method according to any one of Examples 1 to 16, the method comprising the steps of:

[0079] - Provide a composition comprising a compound as defined in any one of Examples 1 to 14, in particular Compound 1;

[0080] - Apply the composition to a plant crop or its locus.

[0081] As in Example 19, there is provided the use of a compound as defined in any one of Examples 1 to 14 for controlling or preventing infestation of cereal plants by the phytopathogenic microorganism Fusarium pseudograminearum, in particular for controlling or preventing infestation of wheat and barley, more particularly wheat.

[0082] As in Example 20, there is provided a method for growing cereal plants, the method comprising applying to the cereal plants or their seeds a compound as defined in any one of Claims 1 to 14 or treating the cereal plants or their seeds with the compound.

[0083] As in another Example 21, the method according to Example 20 is applied as a seed treatment. In particular, the preferred application rate to the seeds is in the range of 0.002 to 0.03 mg AI / seed, more particularly in the range of 0.002 to 0.015 mg AI / seed.

[0084] The preparation of the compounds as defined in the methods according to any one of Examples 1 to 14 has been disclosed in WO 2013 / 143811 and WO 2015 / 003951, which are incorporated herein by reference.

[0085] Definition:

[0086] The term "halogen" means fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.

[0087] The term "alkyl (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 and is, for example, methyl, ethyl, n-propyl, n-butyl, isopropyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl or n-hexyl. Alkyl is suitably C1-C4-alkyl.

[0088] As used herein, "haloalkyl" is alkyl as defined above substituted by one or more identical or different halogen atoms and is, for example, CF3, CF2Cl, CF2H, CCl2H, FCH2, ClCH2, BrCH2, CH3CHF, (CH3)2CF, CF3CH2 or CHF2CH2.

[0089] The method and use according to any one of Embodiments 1 to 21 are preferably used for controlling or preventing crops from being infected by phytopathogenic microorganisms of Fusarium pseudograminearum (including Fusarium fungi resistant to other fungicides). A Fusarium fungus "resistant" to a specific fungicide refers to, for example, a Fusarium strain that is less sensitive to that fungicide compared to the expected sensitivity of the same Fusarium species. The expected sensitivity can be measured using, for example, a strain that has not been previously exposed to the fungicide.

[0090] The application according to the method or use according to any one of Embodiments 1 to 21 is preferably applied to a plant crop, its site, or its seeds. It is preferably applied to a plant crop or its seeds, and more preferably to seeds. The application of the compounds of the present invention can be carried out according to any usual application method (such as foliar application, spraying application, soil application, furrow irrigation application, etc.).

[0091] The compounds as defined in any one of Embodiments 1 to 14 are preferably used at 1 to 500 g / ha for pest control.

[0092] The compounds as defined in any one of Embodiments 1 to 14 are suitable for use on any cereal plant, including those cereal plants that have been genetically modified to be resistant to active ingredients (such as herbicides), or those cereal plants that have been genetically modified to produce biologically active compounds for controlling infestation by plant pests.

[0093] Generally, the compounds as defined in any one of Embodiments 1 to 14 are used in the form of a composition (for example, a formulation) containing a carrier. The compounds as defined in any one of Embodiments 1 to 14 and their compositions can be used in different forms, such as aerosol sprayers, capsule suspensions, cold fogging concentrates, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, encapsulated granulates, fine granules, flowable concentrates for seed treatment, gases (under pressure), gas-generating products, granules, hot fogging concentrates, large granules, microgranules, oil-dispersible powders, oil-miscible flowable concentrates, oil-miscible liquids, pastes, plant sticks, powders for dry seed treatment, seeds coated with a pest control agent, soluble concentrates, soluble powders, solutions for seed treatment, suspension concentrates (flowable concentrates), ultra-low volume (ulv) liquids, ultra-low volume (ulv) suspensions, water-dispersible granules or tablets, water-dispersible powders for slurry treatment, water-soluble granules or tablets, water-soluble powders for seed treatment, and wettable powders.

[0094] The formulations typically contain a liquid or solid carrier and optionally one or more common formulation aids, which can be solid or liquid aids, such as, for example, non-epoxidized or epoxidized vegetable oils (e.g., epoxidized coconut oil, rapeseed oil or soybean oil), defoamers (e.g., silicone oils), preservatives, clays, inorganic compounds, viscosity regulators, surfactants, binders and / or tackifiers. The compositions can further contain fertilizers, micronutrient donors or other products affecting plant growth, and contain combinations that contain the compounds of the invention and one or more other biological active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides and insecticides.

[0095] The compositions are prepared by methods known per se, for example by grinding, sieving and / or compressing the solid compounds of the invention in the absence of aids, and in the presence of at least one aid, for example by intimately mixing and / or grinding the compounds of the invention with one or more aids. In the case of the solid compounds of the invention, the grinding / comminution of the compounds is carried out to ensure a specific particle size.

[0096] Examples of compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil-dispersible powders, directly sprayable or dilutable solutions, coatable pastes, diluted emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or capsules in polymeric substances, the compositions containing at least one compound as defined in any one of Examples 1 to 14 and the type of composition being chosen to suit the intended purpose and the prevailing circumstances.

[0097] Generally, the compositions contain 0.1% to 99% (in particular 0.1% to 95%) of the compound as defined in any one of Examples 1 to 7 and 1% to 99.9% (in particular 5% to 99.9%) of at least one solid or liquid carrier, and in principle it is possible for 0 to 25% (in particular 0.1% to 20%) of the composition to be surfactant (in each case % means weight percentage). For commercial products, it is generally preferred to have concentrated compositions, and the end user usually uses diluted compositions with substantially lower concentrations of the active ingredient.

[0098] Examples of types of foliage formulations for premix compositions are:

[0099] GR: Granules

[0100] WP: Wettable powders

[0101] WG: Water-dispersible granules (powders)

[0102] SG: Water-soluble granules

[0103] SL: Soluble concentrate

[0104] EC: Emulsifiable concentrate

[0105] EW: Oil-in-water emulsion

[0106] ME: Microemulsion

[0107] SC: Aqueous suspension concentrate

[0108] CS: Aqueous capsule suspension

[0109] OD: Oil-based suspension concentrate, and

[0110] SE: Aqueous suspoemulsion.

[0111] Examples of types of seed treatment formulations for premix compositions are:

[0112] WS: Wettable powder for seed treatment slurries

[0113] LS: Solution for seed treatment

[0114] ES: Emulsion for seed treatment

[0115] FS: Suspension concentrate for seed treatment

[0116] WG: Water-dispersible granules, and

[0117] CS: Aqueous capsule suspension.

[0118] Examples of types of formulations suitable for tank mix compositions are solutions, diluted emulsions, suspensions or mixtures thereof, and dusts.

[0119] For the nature of the formulation, the method of application (such as foliar application, spray application, atomized application, dusting application, broadcasting application, coating application or pouring application) can be selected according to the intended purpose and the environment at the time.

[0120] Tank mix compositions are generally prepared by diluting one or more premix compositions containing different pesticidal agents and optionally additional adjuvants with a solvent (e.g., water).

[0121] Suitable carriers and adjuvants can 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.

[0122] Generally, a tank - mix formulation for foliar or soil application comprises from 0.1% to 20%, especially from 0.1% to 15%, of the desired ingredient and from 99.9% to 80%, especially from 99.9% to 85%, of a solid or liquid adjuvant (including, for example, a solvent such as water), wherein the adjuvant may be a surfactant, the amount thereof being from 0 to 20%, especially from 0.1% to 15%, based on the tank - mix formulation.

[0123] Typically, a premix formulation for foliar application comprises from 0.1% to 99.9%, especially from 1% to 95%, of the desired ingredient and from 99.9% to 0.1%, especially from 99% to 5%, of a solid or liquid adjuvant (including, for example, a solvent such as water), wherein the adjuvant may be a surfactant, the amount thereof being from 0 to 50%, especially from 0.5% to 40%, based on the premix formulation.

[0124] Generally, a tank - mix formulation for seed treatment application comprises from 0.25% to 80%, especially from 1% to 75%, of the desired ingredient and from 99.75% to 20%, especially from 99% to 25%, of a solid or liquid adjuvant (including, for example, a solvent such as water), wherein the adjuvant may be a surfactant, the amount thereof being from 0 to 40%, especially from 0.5% to 30%, based on the tank - mix formulation.

[0125] Typically, a premix formulation for seed treatment application comprises from 0.5% to 99.9%, especially from 1% to 95%, of the desired ingredient and from 99.5% to 0.1%, especially from 99% to 5%, of a solid or liquid adjuvant (including, for example, a solvent such as water), wherein the adjuvant may be a surfactant, the amount thereof being from 0 to 50%, especially from 0.5% to 40%, based on the premix formulation.

[0126] Commercial products will preferably be formulated as concentrates (e.g., premix compositions (formulations)), and the end - user will typically use a diluted formulation (e.g., a tank - mix composition).

[0127] Preferred seed - treatment premix formulations are aqueous suspension concentrates. Conventional treatment techniques and machines such as fluid - bed technology, drum - milling methods, rotostatic seed processors, and drum coaters can be used to apply the formulation to the seeds. Other methods (such as spouted beds) may also be useful. The seeds can be pre - sized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art. The compounds of the present invention are particularly suitable for soil and seed - treatment applications.

[0128] In general, the premix composition of the present invention contains 0.5% to 99.9% by mass, especially 1% to 95%, advantageously 1% to 50% of the desired ingredient and 99.5% to 0.1% by mass, especially 99% to 5% of a solid or liquid adjuvant (including, for example, a solvent such as water), wherein the adjuvant (or auxiliary agent) may be a surfactant, and the amount thereof is 0 to 50% by mass, especially 0.5% to 40% based on the mass of the premix formulation.

[0129] There is provided a method for controlling or preventing cereal plants, especially wheat, from being infected by phytopathogenic microorganisms selected from Pyrenophora tritici-repentis and Septoria tritici, the method comprising applying the compound according to any one of Examples 1 to 14 to a plant crop, its locus or its seeds.

[0130] The present invention will now be illustrated by the following non-limiting examples. All cited documents are incorporated by reference.

[0131] Biological Example

[0132] (A) Demonstration of the variability of the fungicidal activity against fungi from the genus Fusarium

[0133] The aim of this study was to evaluate the in vitro activity of three commercial fungicidal compounds against Fusarium graminearum, Fusarium pseudograminearum and Fusarium subglutinans.

[0134] Treatment agent:

[0135] Product 1 - difenoconazole (Dividend TM FS030), 30 g ai / 1000 ml

[0136] Product 2 - thiabendazole (Tecto TM SC500), 500 g ai / 1000 ml

[0137] Product 3 - fludioxonil (Celest TM FS25), 25 g ai / 1000 ml

[0138] Test dose:

[0139] 100, 10, 1, 0.1, 0.01, 0 mg ai / l (ppm)

[0140] Test organism:

[0141] 1. Fusarium graminearum, strain K6102, isolated from maize seeds from Kansas, USA

[0142] 2. Fusarium pseudograminearum, strain: CBS109956

[0143] (strain nr CBS109956; status: holomorphotype strain of Fusarium pseudograminearum, literature Aoki, T. & O'Donnell, K. 1999, Mycologia [Mycology] 91(4): 597 - 609. Collected by Burgess & Lester, 1980. Isolated from the barley (Poaceae) crown, location New South Wales, Australia)

[0144] 3. Fusarium subglutinans isolated from maize seeds from Lombez, France, strain K6135

[0145] Nutrient medium:

[0146] The culture medium was prepared according to the following formula:

[0147]

[0148] Mycelial growth test:

[0149] The nutrient medium was autoclaved at 121 °C for 20 min and then cooled to 55 °C.

[0150] The fungicide was diluted in sterile water and mixed with the medium to the final concentrations (100, 10, 1, 0.1, 0.01, 0 ppm). Each Petri dish was inoculated with a mycelial disc (6 mm diameter) cut from the edge of a 2 - 3 - day - old source colony of the corresponding Fusarium grown on the nutrient medium. After a 3 - day incubation period at 20 °C in the dark, the diameter of the mycelium (including the agar disc) was measured and the data were converted to % activity.

[0151] The dose - response curve was plotted by graphing the percentage growth activity against the fungicide concentration. The EC50 value was determined graphically. The EC50 is the dose at which 50% growth inhibition occurs.

[0152] Summary:

[0153] The following table shows the determined EC50 values:

[0154]

[0155] Conclusion:

[0156] Product 1 showed good activity against Fusarium graminearum and Fusarium subglutinans, but was 19 - fold less active against Fusarium pseudograminearum compared to Fusarium graminearum.

[0157] Compared with *Fusarium graminearum*, the activity of Product 2 against *Fusarium pseudograminearum* is 5 times lower. The activity against *Fusarium subglutinans* is somewhere in between.

[0158] Product 3 is very active against *Fusarium graminearum* and *Fusarium pseudograminearum* (although it is more active against *Fusarium graminearum*), but very weak against *Fusarium subglutinans*.

[0159] This shows that it cannot be expected that a specific fungicidal active ingredient will have similar biological activities against many different *Fusarium* subspecies.

[0160] (B) Effect of seed treatment on wheat crown rot

[0161] Introduction to crown rot disease in wheat:

[0162] The disease is mainly caused by the fungus *Fusarium pseudograminearum*. Although seedling losses may occur, the main sign of infection is basal browning, and when seasonal conditions induce significant plant stress late in the sowing season, white heads and associated yield losses occur.

[0163] Five wheat test sites were selected across the major wheat-growing regions of Australia. All five sites had a history of crown rot and high stubble load from rotational crops. Soil samples were taken to confirm pathogen pressure. Seeds were treated with a Rotostat seed processor with a slurry volume of 800 ml per 100 kg of seeds. For the trial, sowing was carried out using a 6 - 8 row seeder between June 2 and June 14. The number of plants was counted 35 - 65 days after sowing on 2 x 5 m rows. The number of wheat plants with white heads in each plot was evaluated at full maturity and recorded as a percentage compared to untreated plants used as a reference. Grain yield data was obtained at the end of the season.

[0164] Test site:

[0165]

[0166] Treatment list - Conducting field trials:

[0167]

[0168] *Apron with 17 mL / 100 kg seeds (0.001 mg ai / seed) TM Treatment with XL (metalaxyl-M, ES350)

[0169] **All treatments were applied together with CRUISER (thiamethoxam, FS350) at 50 ml / 100 kg seeds (0.012 mg ai / seed)

[0170] Method:

[0171] Crop Wheat Planting date June 2017 Target application timing Seed treatment Application volume 800 mL / 100 kg Equipment used Rotostat seed processor Plot size Drill width (6 - 8 rows) x 12 - 15 m Replicates 5

[0172] Evaluation:

[0173]

[0174] Final emergence count:

[0175]

[0176] White heads:

[0177]

[0178] Plot yield:

[0179]

[0180] Conclusion:

[0181] Compared with the untreated reference, all treatments T2 - T5 improved crop rooting at the start of the season. The number of white ears was reduced, and this led to an increase in yield at the end of the season.

[0182] However, Compound 1 in Treatment T2 was clearly the best treatment agent and unexpectedly showed a 34% reduction in white ears compared to T1 and a 26% yield benefit compared to T1. The effects of Treatments T3, T4, and T5 were similar compared to T1 and increased the yield in the range of 11% to 15%. These findings show the unexpected effects of using the compound of Example 1 in the method of the present invention. In particular, Compound 1 unexpectedly showed a 26% increase in yield, which is more than twice the yield increase found in current commercial treatments (T3 - T5).

Claims

1. A method for controlling or preventing infestation of cereal plants by the phytopathogenic microorganism *Fusarium pseudograminearum*, said method comprising applying a compound according to formula (I) to a plant crop, its locus or its seeds wherein Y is O, C═O or CR12R13; A is a 5- or 6-membered heteroaromatic ring or a benzene ring, said heteroaromatic ring containing 1 to 3 heteroatoms each independently selected from oxygen, nitrogen and sulfur; said heteroaromatic ring or said phenyl is optionally substituted by one or more R6; R6 are each independently halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-halosulfanyl, C1-C4-alkoxy-C1-4-alkyl, or C1-C4-haloalkoxy-C1-C4-alkyl; R1, R2, R3, R4, R12 and R13 are each independently hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl, R5 is hydrogen, methoxy or hydroxy, B is a phenyl substituted by one or more R8, R8 are each independently halogen, cyano or the group -L-R9, where each L is independently 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 each independently C1-C6-alkyl unsubstituted or substituted by one or more R10, C3-C6-cycloalkyl unsubstituted or substituted by one or more R10, C6-C14-bicycloalkyl unsubstituted or substituted by one or more R10, C2-C6-alkenyl unsubstituted or substituted by one or more R10, C2-C6-alkynyl unsubstituted or substituted by R10, phenyl unsubstituted or substituted by R10, or heteroaryl unsubstituted or substituted by one or more R10, R10 are each independently halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-halosulfanyl, C3-C6-alkenyloxy or C3-C6-alkynyloxy; or a salt or N-oxide thereof; wherein B and A-CO-NR5 are cis to each other on the four-membered ring, or a tautomer or stereoisomer of these compounds.

2. The method according to claim 1, wherein Y is O or CH2; A is a 6-membered heteroaromatic ring or a benzene ring, said heteroaromatic ring containing 1 to 2 nitrogen atoms; said heteroaromatic ring or said phenyl is optionally substituted by one or more R6; R6 are each independently 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; R8 are each independently selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy and C3-C6-cycloalkyl.

3. The method according to claim 1 or claim 2, wherein, A is a 6-membered heteroaromatic ring or a benzene ring, the heteroaromatic ring containing 1 to 2 nitrogen atoms and having 1 to 3 substituents selected from R6, and the benzene ring having 1 or 3 substituents selected from R6.

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

5. The method according to any one of claims 1 to 4, wherein Y is CH2; B is phenyl mono- or di-substituted by halogen; A is selected from phenyl, pyrazinyl and pyridinyl, each of which is mono- or di-substituted by a substituent independently selected from halogen and C1-C4-haloalkyl; R1, R2, R3, R4 and R5 are each hydrogen.

6. The method according to any one of claims 1 to 5, wherein, The compound is a compound having formula (Ic) wherein R11 and R12 are independently selected from halogen; A is pyridinyl, which is substituted by one or two substituents independently selected from halogen and C1-C4-haloalkyl.

7. The method according to any one of claims 1 to 6, wherein A is selected from R13 is C1-C4-haloalkyl.

8. The method according to claim 1, wherein, The compound is selected from any one of compounds 1 to 7 having formula (Ic) wherein R11, R12 and A are as defined in the following table: 。 9. The method according to claim 8, wherein, The compound has formula (Ic) wherein R11, R12 and A are as defined in the following table: 。 10. The method according to any one of claims 1 to 9, wherein Apply the compound to the seeds.

11. The method according to claim 10, wherein The application rate to the seeds is in the range of 0.002 to 0.03 mg AI / seed.

12. Use of a compound as defined in any one of claims 1 to 9 for controlling or preventing infection of cereal plants by the phytopathogenic microorganism Fusarium pseudograminearum.

13. A method for growing cereal plants, the method comprising applying to its seeds a compound as defined in any one of claims 1 to 9 or treating its seeds with the compound.

14. The method according to claim 13, wherein The application rate is in the range of 0.002 to 0.03 mg AI / seed.

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