Method for controlling or preventing cereal plants from being infected by the plant pathogenic microorganism Fusarium graminearum

Abstract

The present invention relates to a method for controlling or preventing cereal plants from being infected by the phytopathogenic microorganism Fusarium graminearum, which method comprises applying to the plant crop, its locus or its seeds a compound according to formula (I), wherein R1, R2, R3, R4, R5, Y, A, B are as defined herein.

Description

Technical Field

[0001] The present invention relates to a method for controlling or preventing infection of cereal plants by the phytopathogenic microorganism Fusarium pseudograminearum. Background Art

[0002] Crown rot is one of the biggest diseases causing yield-robbing in wheat. Crown rot is caused primarily by the plant pathogenic fungus Fusarium pseudograminearum. Across the United States, average winter wheat losses due to crown rot are estimated to be as high as 9.5% across large areas of the Pacific Northwest, and similar losses are seen in other western states of the United States. In addition to 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 greatest relative importance in Australia's northern grain production regions. Experts believe that the recent surge in crown rot prevalence in Australia is due to the fact that cereals are grown in tighter rotations and stubble practices have become more common. In addition, in seasons where environmental conditions permit, crown rot may reduce wheat yields by up to 100% in Australia and up to 65% in North America.

[0003] Therefore, there is a continuing need to find improved methods for treating diseases associated with the phytopathogenic fungus F. graminearum.Accordingly, the present invention provides additional methods for controlling or preventing infection of cereal plants by the phytopathogenic microorganism F. graminearum. DETAILED DESCRIPTION

[0004] Cyclobutylcarboxamide compounds and methods for their preparation have been disclosed in WO 2013 / 143811 and WO 2015 / 003951. It has now been surprisingly found that specific cyclobutylcarboxamide compounds disclosed in WO 2013 / 143811 and / or WO 2015 / 003951 are very effective in controlling or preventing infection of cereal plants by the phytopathogenic microorganism Fusarium pseudograminearum. These very effective compounds therefore provide farmers with an important new solution for controlling or preventing crown rot diseases in cereal plants, in particular wheat and barley, more particularly wheat.

[0005] Therefore, as in embodiment 1, there is provided a method for controlling or preventing cereal plants from being infected by the plant pathogenic microorganism Fusarium pseudograminearum, the method comprising applying a compound according to formula (I) to the plant crop, its locus or its seeds

[0006]

[0007] in

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

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

[0010] R6 are independently halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-haloalkylthio, C1-C4-alkoxy-C1-4-alkyl, or C1-C4-haloalkoxy-C1-C4-alkyl;

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

[0012] R5 is hydrogen, methoxy or hydroxy,

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

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

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

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

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

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

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

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

[0021] or tautomers or stereoisomers of these compounds.

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

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

[0024] Y is O or CH2;

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

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

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

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

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

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

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

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

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

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

[0035] Y is CH2;

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

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

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

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

[0040]

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

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

[0043] Therefore, as embodiment 7, there is provided a method according to embodiment 1, wherein the compound has formula (Ia)

[0044]

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

[0046] Mixtures are also understood as part of the present invention, which mixtures contain up to 50%, preferably up to 40%, more preferably up to 30%, especially up to 20%, advantageously up to 10%, desirably up to 5%, in particular up to 3% of the trans stereoisomer of the compound of formula (I) (i.e. wherein the B and AC(=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, especially greater than 4:1, advantageously greater than 9:1, desirably greater than 20:1, in particular greater than 35:1.

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

[0048] In addition, as in embodiment 10, a method for controlling or preventing cereal plants from being infected by the plant pathogenic microorganism Fusarium pseudograminearum is provided, the method comprising applying a compound according to formula (Ic) to the plant crop, its locus or its seeds

[0049]

[0050] in

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

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

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

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

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

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

[0057] A is selected from

[0058]

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

[0060] As embodiment 13, there is provided a method according to any one of embodiments 10 to 12, wherein the compound is selected from any one of compounds 1 to 7 having formula (Ic)

[0061]

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

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

[0064] As embodiment 14, there is provided a method according to any one of embodiments 10 to 12, wherein the compound has formula (Ic)

[0065]

[0066] Wherein R11, R12 and A are as defined in the following table:

[0067] Compound A R11 R12 1 2-Trifluoromethyl-pyridin-3-yl Cl Cl

[0068] The compound of embodiment 14, i.e. compound 1, when used as a seed treatment agent for wheat seeds, has shown an unexpectedly strong biological activity to pseudo graminearum Fusarium. Especially, compared with commercial seed treatment agents (see biological examples part), compound 1 not only shows that the amount of white spikes increased is reduced, and compared with commercial treatment agents, compound 1 also significantly increases the yield of wheat. In fact, compared with other commercial treatment agents, the increase in output when compound 1 is used as a seed treatment agent is greater than twice. This is unexpected, because the technician knows that the activity level that a class of compounds has to a particular species of Fusarium fungi (see biological examples) cannot be predicted.

[0069] As embodiment 15, there is provided a method according to any one of embodiments 1 to 14, wherein the cereal plant is wheat or barley, in particular wheat.

[0070] As embodiment 16, there is provided a method according to any one of embodiments 1 to 15, wherein the compound as defined in any one of embodiments 1 to 14 is applied as a seed treatment agent. In particular, the preferred application amount to the seed is in the range of 0.002 and 0.03 mg AI / seed.

[0071] As embodiment 17, there is provided a method according to any one of embodiments 1 to 16, the method comprising the following steps:

[0072] - providing a composition comprising a compound as defined in any one of embodiments 1 to 14 (particularly compound 1);

[0073] - applying the composition to seeds;

[0074] - Planting said seeds.

[0075] As embodiment 18, there is provided a method according to any one of embodiments 1 to 16, the method comprising the following steps:

[0076] - providing a composition comprising a compound as defined in any one of embodiments 1 to 14 (particularly compound 1);

[0077] - applying the composition to a crop of plants or the locus thereof.

[0078] As embodiment 19, there is provided the use of a compound as defined in any one of embodiments 1 to 14 for controlling or preventing infection of cereal plants by the plant pathogenic microorganism Fusarium graminearum, in particular for controlling or preventing infection of wheat and barley, more particularly wheat.

[0079] As embodiment 20, there is provided a method for growing cereal plants, the method comprising applying a compound as defined in any one of embodiments 1 to 14 to the cereal plants or their seeds or treating the cereal plants or their seeds with the compound.

[0080] As another embodiment 21, the method according to embodiment 20 is applied as a seed treatment. In particular, the preferred application rate to the seeds is in the range of 0.002 and 0.03 mg AI / seed, more particularly in the range of 0.002 and 0.015 mg AI / seed.

[0081] The preparation of compounds as defined in the method of any one of embodiments 1 to 14 has been disclosed in WO 2013 / 143811 and WO 2015 / 003951, which are incorporated herein by reference.

[0082] definition:

[0083] The term "halogen" denotes fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.

[0084] The term "alkyl" as used herein alone or as part of a larger group such as alkoxy, alkylthio, alkoxycarbonyl and alkylcarbonyl is straight or branched and is, for example, methyl, ethyl, n-propyl, n-butyl, isopropyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl or n-hexyl. Alkyl is suitably C1-C4-alkyl.

[0085] As used herein, "haloalkyl" is an alkyl group as defined above substituted by one or more identical or different halogen atoms, and is, for example, CF3, CF2Cl, CF2H, CCl2H, FCH2, ClCH2, BrCH2, CH3CHF, (CH3)2CF, CF3CH2 or CHF2CH2.

[0086] The methods and uses according to any one of embodiments 1 to 21 are preferably used to control or prevent infestation of crops with plant pathogenic microorganisms of the pseudo-graminearum Fusarium species, including Fusarium species that are resistant to other fungicides. A Fusarium species that is "resistant" to a particular fungicide refers, for example, to a Fusarium strain that is less sensitive to that fungicide than the expected sensitivity of the same Fusarium species. The expected sensitivity can be measured, for example, using a strain that has not been previously exposed to the fungicide.

[0087] The application according to the method or use according to any one of embodiments 1 to 21 is preferably applied to plant crops, their sites or their seeds. Preferably applied to plant crops or their seeds, more preferably applied to seeds. The application of the compound of the present invention can be carried out according to any common application mode (e.g., leaf application, spray application, soil application, furrow irrigation application, etc.).

[0088] The compounds as defined in any one of embodiments 1 to 14 are preferably used for pest control at 1 to 500 g / ha.

[0089] The compounds as defined in any one of embodiments 1 to 14 are suitable for use on any cereal plant, including those cereal plants which have been genetically modified to be resistant to active ingredients such as herbicides, or those cereal plants which have been genetically modified to produce biologically active compounds for controlling infestation by plant pests.

[0090] Typically, the compound as defined in any one of embodiments 1 to 14 is used in the form of a composition (e.g., formulation) containing a carrier. The compound as defined in any one of embodiments 1 to 14 and its composition can be used in different forms, such as aerosol sprays, capsule suspensions, cold atomization concentrates, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, encapsulated granules, fine granules (fine granules, flowable concentrates for seed treatment, gases (under pressure), gas-producing products, granules, thermal atomization concentrates, macrogranules, microgranules, oil dispersible powders, oil miscible flowable concentrates, oil miscible liquids, pastes, plant sticks, powders for dry seed treatment, seeds coated with pesticides, soluble concentrates, soluble powders, solutions for seed treatment, suspension concentrates (flowable concentrates), ultra low volume (ulv) liquids, ultra low volume (ulv) suspensions, water dispersible granules or tablets, water dispersible powders for slurry treatment, water soluble granules or tablets, water soluble powders for seed treatment and wettable powders.

[0091] The formulation typically comprises a liquid or solid carrier and optionally one or more conventional formulation adjuvants, which may be solid or liquid adjuvants, for example, non-epoxidized or epoxidized vegetable oils (e.g., epoxidized coconut oil, rapeseed oil or soybean oil), defoamers (e.g., silicone oils), preservatives, clays, inorganic compounds, viscosity modifiers, surfactants, adhesives and / or tackifiers. The composition may further comprise fertilizers, micronutrient donors or other preparations that affect plant growth, and comprises combinations containing the compounds of the invention and one or more other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides and insecticides.

[0092] The compositions are prepared in a manner known per se, in the absence of auxiliaries, for example by grinding, sieving and / or compressing the solid compound according to the invention, and in the presence of at least one auxiliary, for example by intimately mixing and / or grinding the compound according to the invention together with one or more auxiliary agents. In the case of the solid compound according to the invention, the grinding / milling of the compound is to ensure a specific particle size.

[0093] Examples of compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersibles, directly sprayable or dilutable solutions, spreadable pastes, diluted emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or capsules in a polymeric substance, the composition comprising at least one compound as defined in any one of embodiments 1 to 14 and the type of composition being chosen to suit the intended purpose and the prevailing circumstances.

[0094] Typically, the composition comprises 0.1% to 99% (especially 0.1% to 95%) of a compound as defined in any one of embodiments 1 to 7 and 1% to 99.9% (especially 5% to 99.9%) of at least one solid or liquid carrier, and in principle it is possible that 0 to 25% (especially 0.1% to 20%) of the composition is a surfactant (% means weight percentage in each case). While for commercial products, concentrated compositions tend to be preferred, end users generally use diluted compositions with substantially lower concentrations of active ingredients.

[0095] Examples of leaf formulation types for use in premix compositions are:

[0096] GR: Granules

[0097] WP: Wettable Powder

[0098] WG: Water dispersible granules (powders)

[0099] SG: Water-soluble granules

[0100] SL: Soluble Concentrate

[0101] EC: Emulsifiable Concentrate

[0102] EW: Oil in water emulsion

[0103] ME: Microemulsion

[0104] SC: Aqueous Suspension Concentrate

[0105] CS: Aqueous Capsule Suspension

[0106] OD: Oil-based suspension concentrates, and

[0107] SE: aqueous suspension emulsion.

[0108] While examples of the types of seed treatment formulations useful in premix compositions are:

[0109] WS: Wettable powder for seed treatment slurry

[0110] LS: Solution for seed treatment

[0111] ES: Emulsion for seed treatment

[0112] FS: Suspension concentrate for seed treatment

[0113] WG: water dispersible granules, and

[0114] CS: aqueous capsule suspension.

[0115] Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions or mixtures thereof, and dusts.

[0116] As for the nature of the formulation, the method of application (such as foliar application, spray application, atomization application, atomization application, dusting application, broadcasting application, coating application or pouring application) can be selected according to the intended purpose and the prevailing circumstances.

[0117] Tank-mix compositions are generally prepared by diluting one or more premix compositions containing different pesticides and, optionally, additional adjuvants with a solvent (eg, water).

[0118] Suitable carriers and adjuvants can be solid or liquid and are the substances customary in formulation technology, for example natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.

[0119] Generally, tank-mix formulations for foliar or soil application contain 0.1% to 20%, especially 0.1% to 15%, of the desired ingredients and 99.9% to 80%, especially 99.9% to 85%, of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 20%, especially 0.1% to 15%, based on the tank-mix formulation.

[0120] Typically, premix formulations for foliar application contain 0.1% to 99.9%, especially 1% to 95%, of the desired ingredient and 99.9% to 0.1%, especially 99% to 5%, of a solid or liquid adjuvant (including, for example, a solvent such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 50%, especially 0.5% to 40%, based on the premix formulation.

[0121] Typically, tank-mix formulations for seed treatment applications contain 0.25% to 80%, especially 1% to 75%, of the desired ingredients and 99.75% to 20%, especially 99% to 25%, of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 40%, especially 0.5% to 30%, based on the tank-mix formulation.

[0122] Typically, premix formulations for seed treatment applications contain 0.5% to 99.9%, especially 1% to 95%, of the desired ingredients and 99.5% to 0.1%, especially 99% to 5%, of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 50%, especially 0.5% to 40%, based on the premix formulation.

[0123] Whereas commercial products will preferably be formulated as concentrates (eg, premix compositions (formulations)), the end user will typically use a diluted formulation (eg, a tank-mix composition).

[0124] Preferred seed treatment premix formulations are aqueous suspension concentrates. Conventional processing techniques and machines, such as fluidized bed technology, drum milling methods, rotostatic seed processors and drum coaters, can be used to apply the formulation to the seed. Other methods (such as spouted beds) may also be useful. The seeds may be pre-sized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art. The compound of the present invention is particularly suitable for soil and seed treatment applications.

[0125] In general, the premix composition of the present invention contains 0.5% to 99.9%, in particular 1% to 95%, advantageously 1% to 50% by mass of the desired ingredients and 99.5% to 0.1%, in particular 99% to 5% by mass of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant (or adjuvant) may be a surfactant, in an amount of 0 to 50%, in particular 0.5% to 40%, by mass, based on the mass of the premix formulation.

[0126] Provided is a method for controlling or preventing cereal plants, especially wheat, from being infected by phytopathogenic microorganisms selected from Pyricularia tritici and Septoria tritici, the method comprising applying a compound according to any one of embodiments 1 to 14 to a plant crop, a locus thereof or a seed thereof.

[0127] The invention will now be illustrated by the following non-limiting examples.All cited documents are incorporated by reference.

[0128] Biological Examples

[0129] (A) Demonstration of variability in fungicidal activity against fungi from the genus Fusarium

[0130] 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.

[0131] Treatment agent:

[0132] Product 1-Difenoconazole (Dividend TM FS030), 30g ai / 1000ml

[0133] Product 2 - Thiabendazole TM SC500), 500g ai / 1000ml

[0134] Product 3-Fludioxonil (Celest TM FS25), 25g ai / 1000ml

[0135] Test dose:

[0136] 100, 10, 1, 0.1, 0.01, 0mg ai / l (ppm)

[0137] Test organisms:

[0138] 1. Fusarium graminearum strain K6102 isolated from corn seeds from Kansas, USA

[0139] 2. Pseudomonas graminearum, strain: CBS 109956

[0140] (strain nr CBS 109956; status: full type strain of Pseudomonas graminearum, reference Aoki, T. & O'Donnell, K. 1999, Mycologia [Mycology] 91 (4): 597-609. Collected by Burgess & Lester, 1980. Isolated from barley (Poaceae) crown, location, New South Wales, Australia)

[0141] 3. Fusarium gloeosporioides strain K6135 isolated from corn seeds from Lombe, France

[0142] Nutrient medium:

[0143] The culture medium was prepared according to the following recipe:

[0144]

[0145] Mycelial growth test:

[0146] The nutrient medium was autoclaved at 121 °C for 20 min and then cooled to 55 °C.

[0147] The fungicides were diluted in sterile water and mixed with the culture medium to a final concentration (100, 10, 1, 0.1, 0.01, 0 ppm). Each petri dish was inoculated with a mycelial disk (6 mm diameter) cut from the edge of a 2 to 3 day old source colony of the corresponding Fusarium grown on nutrient medium. After a 3 day incubation period at 20°C in the dark, the diameter of the mycelium (including the agar disk) was measured and the data converted to % activity.

[0148] Dose response curves were prepared by plotting the percent growth activity against the fungicide concentration. EC50 values ​​were determined graphically. EC50 is the dose at which 50% growth inhibition occurs.

[0149] Summarize:

[0150] The following table shows the determined EC50 values:

[0151]

[0152] in conclusion:

[0153] Product 1 showed good activity against Fusarium graminearum and Fusarium gloeosporioides, but was 19 times less active against Fusarium pseudograminearum compared to Fusarium graminearum.

[0154] Product 2 was 5 times less active against F. pseudograminearum than F. graminearum. The activity against F. gloeosporioides was somewhere in between.

[0155] Product 3 was very active against F. graminearum and F. pseudograminearum (although more active against F. graminearum), but very weak against F. gloeosporioides.

[0156] This suggests that a particular fungicidal active ingredient cannot be expected to have similar biological activity against many different Fusarium subspecies.

[0157] (B) Effects of seed treatment on wheat crown rot

[0158] Crown rot in wheat Introduction:

[0159] The disease is primarily caused by the fungus Fusarium graminearum. Although seedling losses may occur, the main signs of infection are browning of the base and, when seasonal conditions induce significant plant stress late in the planting season, white ear and associated yield losses.

[0160] Five wheat trial sites were selected across the main wheat growing regions of Australia. All five sites had a history of crown rot and high stubble loads from easy rotation crops. Soil samples were taken to confirm pathogen pressure. Seeds were treated with a Rotostat seed processor with 800 ml slurry volume per 100 kg of seeds. For the trial, planting was carried out using a 6 to 8 row seeder between June 2 and June 14. The number of plants was counted 35-65 days after sowing on 2×5m rows. The number of wheat plants with white ears per plot was assessed at full maturity and recorded as % compared to untreated plants as a reference. Grain yield data were obtained at the end of the season.

[0161] Test location:

[0162]

[0163] Treatment List - Field Trial:

[0164]

[0165] * Treatment with 17 mL / 100 kg seeds (0.001 mg ai / seed) of Apron™ XL (Metalaxyl-M, ES350)

[0166] **All treatments were applied with 50 ml / 100 kg seed (0.012 mg ai / seed) of CRUISER (thiamethoxam, FS350)

[0167] method:

[0168] crop wheat Planting date June 2017 Target administration timing Seed treatment Application volume 800mL / 100kg Equipment used Rotostat Seed Processor Plot size Seeder width (6-8 rows) x 12-15m repeat 5

[0169] Evaluate:

[0170]

[0171] Final emergence count:

[0172]

[0173] White spike:

[0174]

[0175]

[0176] Sample plot yield:

[0177]

[0178] in conclusion:

[0179] All treatments T2-T5 improved crop rooting at the beginning of the season compared to the untreated reference, reduced the number of white spikes, and this led to an increase in yield at the end of the season.

[0180] However, Compound 1 in treatment T2 was clearly the best treatment and unexpectedly showed a 34% reduction in white ears compared to T1 and a 26% yield benefit compared to T1. Treatments T3, T4, and T5 all had similar effects and increased yields in the range of 11% to 15% compared to T1. These findings show the unexpected effects of using the compounds of Example 1 in the methods of the present invention. In particular, Compound 1 unexpectedly showed a 26% yield increase, which is more than twice the yield increase found in current commercial treatments (T3-T5).

Claims

1. A method for controlling or preventing cereal plants from being infected by the plant pathogenic microorganism Fusarium graminearum, the method comprising applying to the plant crop, its locus or its seeds a compound according to formula (Ic) Wherein R11, R12 and A are as defined in the following table: 。 2. The method according to claim 1, wherein: The compound is applied to the seeds.

3. The method according to claim 2, wherein: The application rate to the seeds was in the range of 0.002 to 0.03 mg AI / seed.

4. Use of a compound as defined in claim 1 for controlling or preventing infection of cereal plants by the phytopathogenic microorganism Fusarium graminearum.

5. A method for growing cereal plants, said method comprising applying to seeds thereof a compound as defined in claim 1 or treating seeds thereof with said compound.

6. The method according to claim 5, wherein: The application rate was in the range of 0.002 to 0.03 mg AI / seed.

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