Methods of controlling or preventing infestation of plants by the phytopathogenic microorganism phyllachora maydis

Abstract

The invention relates to methods for controlling or preventing infestation of a plant by the phytopathogenic microorganism Phyllachora maydis, comprising applying to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to a propagation material thereof, a fungicidally effective amount of a compound as defined in claim 1.

Description

109936 FF1METHODS OF CONTROLLING OR PREVENTING INFESTATION OF PLANTS BY THE PHYTOPATHOGENIC MICROORGANISM PHYLLACHORA MAYDISTECHNICAL FIELD

[0001] The present invention relates to methods for controlling or preventing infestation of a plant by the phytopathogenic microorganism Phyllachora maydis.BACKGROUND

[0002] Phyllachora maydis is an obligate plant pathogenic fungus that infects maize or corn Zea mays. It is most commonly referred to as tar spot (Ruhl et al., 2016; Valle-Torres et al., 2020). After a theorized latent period, the fungus produces black fruiting structures (stromata) which resemble tar on the foliage of the corn plant. In severe infections, Phyllachora maydis can cause necrosis on the leaves and premature plant death resulting in greatly diminished yields and grain quality. It was most commonly foundjn Central and South America, particularly in Guatamala, Columbia, Mexico, Peru, however in 2015 it was first observed in the United States and has since been found in numerous parts of the North central / North eastern United States of America and Canada.

[0003] Phyllachora maydis is a member of the order Phyllachorales. Fungi in this order are thought to be obligate biotrophs and require a living host for growth and reproduction. They are considered to be non-culturable (Ruhl et al., 2016) which renders their study under controlled conditions or in vitro difficult. A method to induce tar spot of corn in controlled conditions, in greenhouse and growth chamber, has been developed as an alternative to culturing this fungi (Solorzano et al., 2023).

[0004] WO 2024 / 068518 A1 discloses 3-heteroaryl-5-chlorodifluoromethyl-1 ,2,4-oxadiazole compounds and their use for controlling phytopathogenic fungi in crop protection.

[0005] The development of new classes of agrochemical fungicides is on-going, many of these new classes of chemistry have limitations in their fungicidal spectrum and control only specific phytopathogens. That is to say that, when a new class of chemistry is shown to control specific phytopathogens on specific crops, it cannot be expected that the same class of chemistry will prove useful in the control of the phytopathogen.

[0006] Therefore there exists a need for the development of new methods for controlling or preventing infestation by the phytopathogen Phyllachora maydis.BRIEF SUMMARY

[0007] It has now been surprisingly found that particular carboxamide quinoline compounds disclosed in WO 2017 / 153380 are highly effective at controlling or preventing the infestation of plants by the phytopathogenic microorganism Phyllachora maydis. These highly effective compounds thus represent an important new solution for farmers to control or prevent infestation of plants by the phytopathogenic microorganism Phyllachora maydis. Such carboxamide quinoline compounds and processes for their preparation have been disclosed in WO 2017 / 153380. Preparation of relevant phenyl ethyl amine intermediates has been disclosed in WO 2021 / 110859.109936 FF2

[0008] Hence, there is provided a method of controlling or preventing infestation of plants by the phytopathogenic microorganism Phyllachora maydis comprising applying to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to a propagation material thereof, a fungicidally effective amount of the compound of formula (I):or an enantiomer thereof.

[0009] Preferably, the compound of formula (I) is a combination of the R-enantiomer of the compound of formula (I) (i.e. compound of formula (l-R)) and of the S-enantiomer of the compound of formula (I) (i.e. compound of formula (l-S)), in a molar ratio (l-R) : (l-S) greater than 1.5 : 1 , greater than 2.5 : 1 , greater than 4 : 1 , or greater than 9 : 1.

[0010] There is also provided the use of a compound of formula (I) for controlling or preventing infestation of plants by the phytopathogenic microorganism Phyllachora maydis.

[0011] It has also been found that the compound of formula (I) may be used to control or prevent leaf senescence of cultivated plants, in particular when said cultivated plant is infected by the phytopathogenic microorganism Phyllachora maydis. Therefore, there is also provided the use of a compound of formula (I) for controlling or preventing leaf senescence of cultivated plants, in particular when said cultivated plant is infected by the phytopathogenic microorganism Phyllachora maydis.

[0012] Preferably, in these methods or uses, the plant is corn or maize Zea mays.

[0013] Also preferably, in these methods or uses, the compound of formula (I) is Feneptamidoquin.DESCRIPTION OF THE DRAWINGS

[0014] Figure 1 shows the disease severity (Tar spot on Corn) at 22, 46 and 56 days after last application with various fungicides: untreated control (A), Trivapro® at 265 g ai / ha (B), Compound l-A at 100 g ai / ha (C), Compound l-A at 200 g ai / ha (D), and Tilt® at 125 g ai / ha (E). g ai / ha = grams of active ingredient (ai) per hectare.

[0015] Figure 2 shows leaf senescence at 56 days after last treatment, using the same treatments as in Figure 1 .

[0016] Figure 3 shows the disease severity (Tar spot on Corn) at 38 days after last application with various fungicides having a DHODH inhibitor mode of action (according to WO 2022 / 129200).

[0017] Figure 4 shows the disease severity (Tar spot on Corn) at 53 days after application with various fungicides: A = untreated control, B = Feneptamidoquin at 125 g ai / ha + non-ionic surfactant at 0.125%v / v, and C = Miravis® Neo at 375 g ai / ha + non-ionic surfactant at 0.125%v / v.109936 FF3

[0018] Figure 5 shows the percentage of foliar senescence on Corn infected by Tar spot, 54 days after application with the same treatments as in Figure 4.DETAILED DESCRIPTION

[0019] The chemical name of compound of formula (I) is N-(1-benzyl-1 ,3-dimethyl-butyl)-8-fluoro- quinoline-3-carboxamide. Compound (I) is a racemate compound. It has two enantiomers, identified as compound (l-R) and compound (l-S):(l-R) (l-S)

[0020] Methods for the preparation of compounds (I), (l-R) and (l-S) are described in WO 2017 / 153380 and WO 2021 / 110859. It is part of the common general knowledge of a person skilled in the art how to resolve racemate mixtures, for example by chiral chromatography. Compounds (I), (l-R) and (l-S) have been described as dihydroorotate dehydrogenase (DHODH) inhibitors in WO 2022 / 129200. WO 2024 / 246265, the content of which is fully incorporated therein, describes solid forms of the compound of formula (I).

[0021] In particular, there is also provided a method of controlling or preventing infestation of plants by the phytopathogenic microorganism Phyllachora maydis comprising applying to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to a propagation material thereof, a fungicidally effective amount of the compound of formula (l-R), of the compound of formula compound (l-S), or of a combination of the compound of formula (l-R) and the compound of formula (l-S). In embodiments of the invention, the compound (I) is present as a mixture of the (R) and (S) enantiomers. The racemic compound (I) represents 1 :1 mixture of compound (l-R) and compound (l-S). Preferably, the compound used in the method according to the invention is compound (l-R). When both compound (l-R) and compound (l-S) are present, the ratio of compound (l-R) to compound (l-S) (the “R / S ratio”) is preferably greater than 1 :1. More preferably, the R / S ratio is greater than 1.5:1 , even 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 . As compound (l-R) and compound (l-S) have the same molecular weight, the R / S ratio can be viewed as a molar ratio as well as a weight ratio.

[0022] A skilled person is aware that compound for plant-disease control are generally applied as part of a fungicidal composition. Hence, there is provided a method of controlling or preventing infestation of plants by the phytopathogenic microorganism Phyllachora maydis comprising applying109936 FF4 to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to a propagation material thereof, a fungicidal composition comprising a compound of formula (I), or an enantiomer thereof, and one or more formulation adjuvants.

[0023] There is also provided a method of controlling or preventing infestation of plants by the phytopathogenic microorganism Phyllachora maydis, comprising applying to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to a propagation material thereof, a fungicidal composition comprising compound of formula (l-R), and one or more formulation adjuvants.

[0024] There is also provided a method of controlling or preventing infestation of plants by the phytopathogenic microorganism Phyllachora maydis, comprising applying to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to a propagation material thereof, a fungicidal composition comprising compound of formula (l-S), and one or more formulation adjuvants.

[0025] There is also provided a method of controlling or preventing infestation of plants by the phytopathogenic microorganism Phyllachora maydis, comprising applying to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to a propagation material thereof, a fungicidal composition comprising compound of formula (l-R) and compound of formula (l-S), and one or more formulation adjuvants. For fungicidal compositions comprising both compound (l-R) and compound (l-S), the R / S ratio (as defined above) is preferably greater than 1 :1. More preferably, the R / S ratio is greater than 1.5:1 , even 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.

[0026] Preferably, there is provided a method of controlling or preventing infestation of plants by the phytopathogenic microorganism Phyllachora maydis comprising applying to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to a propagation material thereof, a fungicidally effective amount of compound (l-R) and compound (l-S), where the R / S ratio is greater than 1 .5:1 , even 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 .

[0027] A method of controlling or preventing infestation of plants by the phytopathogenic microorganism Phyllachora maydis may comprise the steps of:• providing a composition comprising a compound of formula (I), (l-R), or (l-S);• applying the composition to a propagation material, such as a seed;• planting the propagation material.

[0028] Alternatively, a method of controlling or preventing infestation of plants by the phytopathogenic microorganism Phyllachora maydis may comprise the steps of• providing a composition comprising a compound of formula (I), (l-R), or (l-S);• applying the composition to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen.109936 FF5

[0029] Further, there is provided the use of a compound as defined above for controlling or preventing infestation of plants by the phytopathogenic microorganism Phyllachora maydis. Specifically, the plant is selected from maize or corn. The method and uses described above are suitable for use on any maize or corn plant, including those that have been genetically modified to be resistant to active ingredients such as herbicides, or to produce biologically active compounds that control infestation by plant pests.

[0030] Examples of maize or corn varieties include Zea mays var. amylacea, Zea mays var. everta, Zea mays var. indentata, Zea mays var. indurata, Zea mays var. saccharata, Zea mays var. rugosa, Zea mays var. ceratina, Zea mays var. tunicata Larranaga ex A. St. Hil. , Zea mays var. japonica. In particular, the plant is a corn or maize useful as, or in for the production of flour corn, popcorn, dent corn, flint corn, sweet corn, waxy corn, amylomaize, pod corn, striped maize, cattle feed, biofuel, silage.

[0031] The term “plants” and / or “target crops” is to be understood as also including plants that have been rendered tolerant to herbicides, to insect as well as to nematodes, as as a result of conventional methods of breeding or genetic engineering, or those varieties which naturally are, or have been rendered, resistant to harmful insects.

[0032] Examples of plants or target cops include plants or target crops that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl- shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) Examples of crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.

[0033] Examples of crops that have been rendered resistant to insects include those which naturally are or have been rendered resistant to harmful insects. This includes plants transformed by the use of recombinant DNA techniques, for example, to be capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria. Examples of toxins which can be expressed include d-endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of bacteria colonising nematodes, and toxins produced by scorpions, arachnids, wasps and fungi. An example of a crop that has been modified to express the Bacillus thuringiensis toxin is the Bt maize KnockOut (Syngenta Seeds). An example of a crop comprising more than one gene that codes for insecticidal resistance and thus expresses more than one toxin is VipCot® (Syngenta Seeds). Crops or seed material thereof can also be resistant to multiple types of pests (so-called stacked transgenic events when created by genetic modification). For example, a plant can have the ability to express an insecticidal protein while at the same time being herbicide tolerant, for example Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).

[0034] The term "plants" and / or “target crops” is to be understood as including also plants which have been so transformed by the use of recombinant DNA techniques that they are capable of109936 FF6 synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-0 392 225). Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95 / 33818, and EP-A-0 353 191. The methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.

[0035] Toxins that can be expressed by transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as d-endotoxins, e.g. CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1 , Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroidoxidase, ecdysteroid-UDP- glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

[0036] Further, in the context of the present invention there are to be understood by d-endotoxins, for example CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1 , Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02 / 15701). Truncated toxins, for example a truncated CrylAb, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3A toxin (see W003 / 018810).

[0037] More examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO93 / 07278, WO95 / 34656, EP-A-0 427 529, EP-A-451 878 and WG03 / 052073.

[0038] The processes for the preparation of such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. Cryl- type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP-A- 0 367 474, EP-A-0 401 979 and WO 90 / 13651.

[0039] The toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).109936 FF7

[0040] Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1 Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium).

[0041] Further examples of such transgenic crops are:

[0042] 1. Bt11 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated CrylAb toxin. Bt11 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

[0043] 2. Bt176 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a CrylAb toxin. Bt176 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

[0044] 3. MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03 / 018810.

[0045] 4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.

[0046] 5. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize for the expression of the protein Cry1 F for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium.

[0047] 6. NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 x MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.

[0048] According to WO 2019 / 052930, compounds (I), (l-R) and (l-S) may be used to control plant pathogenic fungi, especially Venturia, Sclerotinia, Botrytis and Fusarium, which are resistant to one109936 FF8 or more fungicides from any of the following fungicidal MoA classes: sterol demethylation-inhibitors (DMI), quinone-outside-inhibitors (Qol) and succinate dehydrogenase inhibitors (SDHI), anilinopyrimidine (AP), phenylpyrrole (PP) and hydroxyanilide fungicides, dicarboximides, and methyl benzimidazole carbamate (MBC) fungicides. Fungicidal compositions, in particular the binary compositions and ternary compositions, may also be used to control plant pathogenic fungi, especially Venturia, Sclerotinia, Botrytis and Fusarium, which are resistant to one or more fungicides from any of the following fungicidal MoA classes: sterol demethylation-inhibitors (DMI), quinone-outside- inhibitors (Qol) and succinate dehydrogenase inhibitors (SDHI), anilinopyrimidine (AP), phenylpyrrole (PP) and hydroxyanilide fungicides, dicarboximides, and methyl benzimidazole carbamate (MBC) fungicides. Such binary compositions may comprise as component (A), compound (I), compound (I- R) or compound (l-S), and as component (B), pydiflumetofen, benzovindiflupyr, difenoconazole, hexaconazole, azoxystrobin, fludioxonil, cyprodinil, fluazinam, isopyrazam, pyroquilon, tricyclazole, chlorothalonil, propiconazole, aminopyrifen, penconazole, fenpropimorph, fenpropidin, sulfur, and a biofungicide comprising Bacillus subtilis strains, such as Taegro® (a biofungicide comprising Bacillus subtilis var. amyloliquefaciens strain FZB24, available from Novozymes Biologicals Inc., 5400 Corporate Circle, Salem, VA 24153, U.S.A.), Serenade® (based on strain QST713) or Subtilex® (based on strain MBI600).

[0049] Therefore, there are provided methods and uses for controlling or preventing infestation of maize or corn by phytopathogenic microorganism Phyllachora maydis that are resistant to other fungicides. Phyllachora maydis that are "resistant" to a particular fungicide refer e.g. to strains of Phyllachora maydis fungi that are less sensitive to that fungicide compared to the expected sensitivity of the same species of Phyllachora maydis fungi. The expected sensitivity can be measured using e.g. a strain that has not previously been exposed to the fungicide.

[0050] Generally, in methods and uses described above, compound of formula (I), (l-R), and (l-S) will be used in the form of a composition (e.g. formulation) containing a carrier. Such active compounds and compositions thereof can be used in various forms such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment, seed coated with a pesticide, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra low volume (ulv) liquid, ultra low volume (ulv) suspension, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules or tablets, water soluble powder for seed treatment and wettable powder.

[0051] Compositions can be mixed with one or more further pesticides including further fungicides, insecticides, nematicides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active109936 FF9 compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection.

[0052] A formulation typically comprises a liquid or solid carrier and optionally one or more customary formulation auxiliaries, which may be solid or liquid auxiliaries, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, clays, inorganic compounds, viscosity regulators, surfactant, binders and / or tackifiers. The composition may also further comprise a fertilizer, a micronutrient donor or other preparations which influence the growth of plants as well as comprising a combination containing the compound of the invention with one or more other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides.

[0053] The compositions are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and / or compressing a solid compound of the present invention and in the presence of at least one auxiliary for example by intimately mixing and / or grinding the compound of the present invention with the auxiliary (auxiliaries). In the case of solid compounds of the invention, the grinding / milling of the compounds is to ensure specific particle size.

[0054] Examples of compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersibles, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymeric substances, which comprise - at least - a compound as defined above and the type of composition is to be selected to suit the intended aims and the prevailing circumstances.

[0055] As a rule, the compositions comprise 0.1 to 99%, especially 0.1 to 95%, of compound as defined above and 1 to 99.9%, especially 5 to 99.9%, of at least one solid or liquid carrier, it being possible as a rule for 0 to 25%, especially 0.1 to 20%, of the composition to be surfactants (% in each case meaning percent by weight). Whereas concentrated compositions tend to be preferred for commercial goods, the end consumer as a rule uses dilute compositions which have substantially lower concentrations of active ingredient.

[0056] Examples of foliar formulation types for pre-mix compositions are: GR: Granules; WP: wettable powders; WG: water dispersable granules (powders); SG: water soluble granules; SL: soluble concentrates; EC: emulsifiable concentrate; EW: emulsions, oil in water; ME: micro-emulsion; SC: aqueous suspension concentrate ; CS: aqueous capsule suspension; OD: oil-based suspension concentrate; and SE: aqueous suspo-emulsion.

[0057] Whereas examples of seed treatment formulation types for pre-mix compositions are: WS: wettable powders for seed treatment slurry; LS: solution for seed treatment; ES: emulsions for seed treatment; FS: suspension concentrate for seed treatment; WG: water dispersible granules; and CS: aqueous capsule suspension.

[0058] Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions, or a mixture thereof, and dusts.109936 FF10

[0059] As with the nature of the formulations, the methods of application, such as foliar, drench, spraying, atomizing, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.

[0060] The tank-mix compositions are generally prepared by diluting with a solvent (for example, water) the one or more pre-mix compositions containing different pesticides, and optionally further auxiliaries.

[0061] Suitable carriers and adjuvants can be solid or liquid and are the substances ordinarily employed in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.

[0062] Generally, a tank-mix formulation for foliar or soil application comprises 0.1 to 20%, especially 0.1 to 15 %, of the desired ingredients, and 99.9 to 80 %, especially 99.9 to 85 %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 20 %, especially 0.1 to 15 %, based on the tank-mix formulation.

[0063] Typically, a pre-mix formulation for foliar application comprises 0.1 to 99.9 %, especially 1 to 95 %, of the desired ingredients, and 99.9 to 0.1 %, especially 99 to 5 %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation.

[0064] Normally, a tank-mix formulation for seed treatment application comprises 0.25 to 80%, especially 1 to 75 %, of the desired ingredients, and 99.75 to 20 %, especially 99 to 25 %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 40 %, especially 0.5 to 30 %, based on the tank-mix formulation.

[0065] Typically, a pre-mix formulation for seed treatment application comprises 0.5 to 99.9 %, especially 1 to 95 %, of the desired ingredients, and 99.5 to 0.1 %, especially 99 to 5 %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation.

[0066] Whereas commercial products will preferably be formulated as concentrates (e.g., pre-mix composition (formulation)), the end user will normally employ dilute formulations (e.g., tank mix composition).

[0067] Preferred seed treatment pre-mix formulations are aqueous suspension concentrates. The formulation can be applied to the seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful. The seeds may be presized 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 suited for use in soil and seed treatment applications.

[0068] In general, the pre-mix compositions of the invention contain 0.5 to 99.9 especially 1 to 95, advantageously 1 to 50, % by mass of the desired ingredients, and 99.5 to 0.1 , especially 99 to 5, % by mass of a solid or liquid adjuvant (including, for example, a solvent such as water), where the109936 FF11 auxiliaries (or adjuvant) can be a surfactant in an amount of 0 to 50, especially 0.5 to 40, % by mass based on the mass of the pre-mix formulation.

[0069] In addition, further, other biocidally active ingredients or compositions may be combined with the compositions of the invention and used in the methods of the invention and applied simultaneously or sequentially with the compositions of the invention. When applied simultaneously, these further active ingredients may be formulated together with the compositions of the invention or mixed in, for example, the spray tank. These further biocidally active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0070] In addition, the compositions of the invention may also be applied with one or more systemically acquired resistance inducers (“SAR” inducer). SAR inducers are known and described in, for example, United States Patent No. US 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar-S-methyl.

[0071] The compounds as defined above are normally used in the form of compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be e.g. fertilizers or micronutrient donors or other preparations, which influence the growth of plants. They can also be selective herbicides or non- selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.

[0072] The compounds as defined above may be used in the form of (fungicidal) compositions for controlling or protecting corn or maize against the phytopathogen Phyllachora maydis, comprising as active ingredient at least one compound (I), (l-R) and (l-S), in free form or in agrochemically usable salt form, and at least one of the above-mentioned adjuvants.

[0073] The term “locus” as used herein means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation.

[0074] The term “plants” refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.

[0075] The term “plant propagation material” is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. There may be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion. Preferably “plant propagation material” is understood to denote seeds.

[0076] Pesticidal agents referred to herein using their common name are known, for example, from "The Pesticide Manual", 15th Ed., British Crop Protection Council 2009.

[0077] The compounds of formula (I), (l-R) or (l-S) for use in the inventive methods may be the sole active ingredient of a composition or it may be admixed with one or more additional active ingredients109936 FF12 such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate. An additional active ingredient may, in some cases, result in unexpected synergistic activities.

[0078] The compositions according to the invention can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and / or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.

[0079] The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and / or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and / or grinding the active ingredient with the auxiliary (auxiliaries). These processes for the preparation of the compositions and the use of the compounds (I) for the preparation of these compositions are also a subject of the invention.

[0080] Another aspect of the invention is related to the use of a a compound as defined above, of a composition comprising at least one compound as defined in, or of a fungicidal or insecticidal mixture comprising at least one compound as defined above, in admixture with other fungicides or insecticides as described above, for controlling or preventing infestation of plants, e.g. plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living materials by insects or by phytopathogenic microorganisms, preferably fungal organisms.

[0081] A further aspect of invention is related to a method of controlling or preventing an infestation of plants, e.g. plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or of non-living materials by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, which comprises the application of a compound as defined above as active ingredient to the plants, to parts of the plants or to the locus thereof, to the propagation material thereof, or to any part of the non-living materials.

[0082] Controlling or preventing means reducing infestation by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, to such a level that an improvement is demonstrated.

[0083] A preferred method of controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects which comprises the application of a compound as defined above, or an agrochemical composition which contains at least one of said compounds, is foliar application. The frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen or insect. However, the compounds of formula (I) can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field. The compounds of formula (I) may also be applied to seeds (coating)109936 FF13 by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.

[0084] Application may be performed as a preventive measure, or once infestation of maize or corn by Phyllachora maydis has already started. Application is preferably to a crop of plants, the locus thereof or propagation material thereof. Preferably application is to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to a propagation material thereof. Application of the compounds can be performed according to any of the usual modes of application, e.g. foliar, drench, soil, in furrow etc. A preferred mode of application is foliar application.

[0085] Depending on the vegetation stage, various agricultural equipment may be used to perform the methods described herein. Agriculture equipment include ground-based machinery such as boom sprayers, tractor-mounted spayers, or self-propelled sprayers, which are all well known in the technical field. Air-based equipments may also be used, such as plane, helicopter or drones. When the infestation is not overly spread in a field, precision sprayers may be used for precise application of the right amount of product to specific areas of the field. This can help minimize waste and reduce environmental impact. Preventive application is also considered. Preventive application may be performed with standard agricultural equipment.

[0086] Compound (I), (l-R), or (l-S), may be used at rates of 50 to 200 g / ha, preferably at rates of 75 to 200 g / ha. Application volumes may be in the range of from 15 to 200 L / ha, preferably from 18 to 180 L / ha. Efficacy may be enhanced with the use of an adjuvant.

[0087] Under normal conditions a single application would be made foliarly to corn at a growth stage anywhere from V10 / V12, VT / R1 , and as late as R3. Under conditions extremely conducive for disease, multiple applications could be made, with the first application made during the vegetation stages (V5 / 6-V10 / 12) and with follow up applications made at the reproductive stages R1 -R3. Vegetative and reproductive stages of corn are described in the publication How a corn plant develops by Steven W. Ritchie, John J Hanway, and Garren O Benson, as revised in January 1986 (Iowa State University of Science and Technology Cooperative Extension Service, Ames, Iowa).

[0088] The invention will now be illustrated by the following non-limiting Examples, all citations are incorporated by reference.EXAMPLESTable X109936 FF

[0089] There is also provided a fungicidal composition comprising a mixture of components (A) and (B) as active ingredients (“binary compositions”), in particular for controlling or preventing infestation of a plant by the phytopathogenic microorganism Phyllachora maydis, wherein component (A) is a compound selected from Table X, namely a component (A) is a compound selected from compound (I), compound (l-R), compound (l-S), and Feneptamidoquin; and component (B) is selected from Aminopyrifen, Azoxystrobin, Benzovindiflupyr, Boscalid, Chlorothalonil, Cyantraniliprole, Cyclobutrifluram, Cyflufenamid, Cyprodinil, Difenoconazole, Fenpropidin, Fenpropimorph, Florylpicoxamid, Fluazinam, Fludioxonil, Fluopyram, Fluxapyroxad, Hexaconazole, Isocycloseram, Isoflucypram, Isopyrazam, Mancozeb, Mefentrifluconazole, Metalaxyl, Metalaxyl-M, Metconazole, Metyltetraprole, Oxathiapiprolin, Penconazole, Picoxystrobin, Propiconazole, Prothioconazole, Pydiflumetofen, Pyraclostrobin, Pyroquilon, Spiropidion, Sulfur, Tebuconazole, Tricyclazole, Triflumezopyrim, TAEGRO® ( / .e., Bacillus amyloliquefaciens strain FZB24), melaluca alternifolia oil (an extract of the tea tree plant Melaluca alternifolia, commercially available as Timorex Gold®, which is a broad-spectrum botanical biofungicide), Reynoutria sachalinensis extract (commercially available as REGALIA®), a plant extract based on the extract of Quillaja saponaria Molina (commercially available as BOTRISTOP®), and Aureobasidin A. “TIMOREX Gold™" or “Timorex Gold®” as used herein refers to melaluca alternifolia oil, which is an extract of the tea tree plant Melaluca alternifolia, commercially available as Timorex GoldR, which is a broad-spectrum botanical biofungicide.

[0090] TAEGRO™ or TAEGRO® as used herein refers to a microorganism-based fungicide formulated as a wettable powder containing 130 g / kg Bacillus amyloliquefaciens strain FZB24, having109936 FF15Accession No. DSM 10271 (13% w / w minimum of 1x1013 cfu / kg), commercially available as TAEGRO®.

[0091] BOTRISTOP® as used herein refers to a broad spectrum biofungicide, a plant extract based on the extract of Quillaja saponaria Molina.

[0092] “REGALIA®” as used herein refers to a biofungicide, a plant extract based on the extract of Reynoutria sachalinensis extract (commercially available as REGALIA®).

[0093] Aureobasidin A is an antifungal cyclic depsipeptide antibiotic produced by Aureobasidium pullulans. See, for instance, Takesako et al., J. of Antibiot 1991 , 44, 919-924. WO 2018 / 102345 discloses use of Aureobasidin A as an agricultural fungicide to treat, prevent or control fungal infections in plants and seeds.

[0094] Preferably, there is provided a fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is selected from Azoxystrobin, Benzovindiflupyr, Boscalid, Chlorothalonil, Cyclobutrifluram, Cyprodinil, Difenoconazole, Fluazinam, Fludioxonil, Hexaconazole, Isocycloseram, Isopyrazam, Mefentrifluconazole, Metalaxyl-M, Oxathiapiprolin, Prothioconazole, Pydiflumetofen, Pyraclostrobin, Spiropidion, and Tebuconazole.

[0095] In general, the weight ratio of component (A) to component (B) may preferably be from 100:1 to 1 :100, from 50:1 to 1 :50, from 20:1 to 1 :40, from 15:1 to 1 :30, from 12:1 to 1 :25, from 10:1 to 1 :20, from 5:1 and 1 :15, from 3:1 to 1 :10 or from 2:1 to 1 :5.

[0096] Preferably, there is also provided a fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is a compound selected from Table X, namely component (A) is a compound selected from compound (I), compound (l-R), compound (l-S), and Feneptamidoquin; and component (B) is selected from Aminopyrifen, Azoxystrobin, Benzovindiflupyr, Boscalid, Chlorothalonil, Cyclobutrifluram, Cyflufenamid, Cyprodinil, Difenoconazole, Fenpropidin, Fenpropimorph, Florylpicoxamid, Fluazinam, Fludioxonil, Fluopyram, Fluxapyroxad, Hexaconazole, Isocycloseram, Isoflucypram, Isopyrazam, Mancozeb, Mefentrifluconazole, Metalaxyl, Metalaxyl-M, Metconazole, Metyltetraprole, Oxathiapiprolin, Penconazole, Picoxystrobin, Propiconazole, Prothioconazole, Pydiflumetofen, Pyraclostrobin, Pyroquilon, Spiropidion, Sulfur, Tebuconazole, Tricyclazole, Triflumezopyrim, TAEGRO® ( / .e., Bacillus amyloliquefaciens strain FZB24), melaluca alternifolia oil (an extract of the tea tree plant Melaluca alternifolia, commercially available as Timorex Gold®, which is a broad-spectrum botanical biofungicide), Reynoutria sachalinensis extract (commercially available as REGALIA®), a plant extract based on the extract of Quillaja saponaria Molina (commercially available as BOTRISTOP®), and Aureobasidin A; wherein the weight ratio of component (A) to component (B) is from 100:1 to 1 :40, preferably from 40:1 to 1 :40, even more preferably from 20:1 to 1 :20, still more preferably from 15:1 to 1 :30, still even more preferably from 10:1 to 1 :10, most preferably from 5:1 to 1 :5 and even most preferably from 2:1 to 1 :2.

[0097] More preferably, there is provided a fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and109936 FF16 component (B) is selected from Azoxystrobin, Benzovindiflupyr, Boscalid, Chlorothalonil, Cyclobutrifluram, Cyprodinil, Difenoconazole, Fluazinam, Fludioxonil, Hexaconazole, Isocycloseram, Isopyrazam, Mefentrifluconazole, Metalaxyl-M, Oxathiapiprolin, Prothioconazole, Pydiflumetofen, Pyraclostrobin, Spiropidion, and Tebuconazole; wherein the weight ratio of component (A) to component (B) is from 100:1 to 1 :40, preferably from 40:1 to 1 :40, even more preferably from 20:1 to 1 :20, still more preferably from 15:1 to 1 :30, still even more preferably from 10:1 to 1 :10, most preferably from 5:1 to 1 :5 and even most preferably from 2:1 to 1 :2.

[0098] For instance, there is provided a fungicidal composition comprising a mixture of components(A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is selected from Azoxystrobin, Benzovindiflupyr, Boscalid, Chlorothalonil, Cyclobutrifluram, Cyprodinil, Difenoconazole, Fluazinam, Fludioxonil, Hexaconazole, Isocycloseram, Isopyrazam, Mefentrifluconazole, Metalaxyl-M, Oxathiapiprolin, Prothioconazole, Pydiflumetofen, Pyraclostrobin, Spiropidion, and Tebuconazole; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20.

[0099] There is also provided there is provided a fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is selected from Azoxystrobin, Benzovindiflupyr, Boscalid, Chlorothalonil, Cyclobutrifluram, Cyprodinil, Difenoconazole, Fluazinam, Fludioxonil, Hexaconazole, Isocycloseram, Isopyrazam, Mefentrifluconazole, Metalaxyl-M, Oxathiapiprolin, Prothioconazole, Pydiflumetofen, Pyraclostrobin, Spiropidion, and Tebuconazole; wherein the weight ratio of component (A) to component (B) is from 15:1 to 1 :30.

[0100] There is also provided there is provided a fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is selected from Azoxystrobin, Benzovindiflupyr, Boscalid, Chlorothalonil, Cyclobutrifluram, Cyprodinil, Difenoconazole, Fluazinam, Fludioxonil, Hexaconazole, Isocycloseram, Isopyrazam, Mefentrifluconazole, Metalaxyl-M, Oxathiapiprolin, Prothioconazole, Pydiflumetofen, Pyraclostrobin, Spiropidion, and Tebuconazole; wherein the weight ratio of component (A) to component (B) is from 10:1 to 1 :5.

[0101] There is also provided a fungicidal composition comprising a mixture of components (A) and(B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is selected from Azoxystrobin, Benzovindiflupyr, Boscalid, Chlorothalonil, Cyclobutrifluram, Cyprodinil, Difenoconazole, Fluazinam, Fludioxonil, Hexaconazole, Isocycloseram, Isopyrazam, Mefentrifluconazole, Metalaxyl-M, Oxathiapiprolin, Prothioconazole, Pydiflumetofen, Pyraclostrobin, Spiropidion, and Tebuconazole; wherein the weight ratio of component (A) to component (B) is from 5:1 to 1 :2.

[0102] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Azoxystrobin; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.109936 FF17

[0103] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Benzovindiflupyr; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0104] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Boscalid; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0105] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Chlorothalonil; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0106] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Cyclobutrifluram; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0107] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Cyprodinil; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0108] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Difenoconazole; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0109] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Fluazinam; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0110] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Fludioxonil; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0111] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Hexaconazole; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0112] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is109936 FF18Isocycloseram; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0113] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Isopyrazam; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0114] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Mefentrifluconazole; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0115] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Metalaxyl-M; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0116] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Oxathiapiprolin; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0117] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Prothioconazole; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0118] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Pydiflumetofen; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0119] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Pyraclostrobin; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0120] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Spiropidion; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.

[0121] Also provided are fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is Feneptamidoquin and component (B) is Tebuconazole; wherein the weight ratio of component (A) to component (B) is from 40:1 to 1 :20, or from 15:1 to 1 :30, or from 10:1 to 1 :5, or from 5:1 to 1 :2.109936 FF19

[0122] Examples of preferred fungicidal compositions comprising Feneptamidoquin as componentA and a component B are given in Table T1 below:Table T1 Feneptamidoquin as component (A), in combination with component (B)

[0123] There is also provided a fungicidal composition comprising a mixture of components (A), (B) and (C) as active ingredients (“ternary compositions”), in particular for controlling or preventing infestation of a plant by the phytopathogenic microorganism Phyllachora maydis, wherein component (A) is a compound selected from Table X, namely component (A) is a compound selected from compound (I), compound (l-R), compound (l-S), and Feneptamidoquin; and components (B) and (C) are differently selected from Aminopyrifen, Azoxystrobin, Benzovindiflupyr, Boscalid, Chlorothalonil, Cyclobutrifluram, Cyflufenamid, Cyprodinil, Difenoconazole, Fenpropidin, Fenpropimorph, Florylpicoxamid, Fluazinam, Fludioxonil, Fluopyram, Fluxapyroxad, Hexaconazole, Isocycloseram, Isoflucypram, Isopyrazam, Mancozeb, Mefentrifluconazole, Metalaxyl, Metalaxyl-M, Metconazole,109936 FF20Metyltetraprole, Oxathiapiprolin, Penconazole, Picoxystrobin, Propiconazole, Prothioconazole, Pydiflumetofen, Pyraclostrobin, Pyroquilon, Spiropidion, Sulfur, Tebuconazole, Tricyclazole, Triflumezopyrim, TAEGRO® ( / .e., Bacillus amyloliquefaciens strain FZB24), melaluca alternifolia oil (an extract of the tea tree plant Melaluca alternifolia, commercially available as Timorex Gold®, which is a broad-spectrum botanical biofungicide), Reynoutria sachalinensis extract (commercially available as REGALIA®), a plant extract based on the extract of Quillaja saponaria Molina (commercially available as BOTRISTOP®), and Aureobasidin A.

[0124] Preferably, component (A) is Feneptamidoquin, and components (B) and (C) are selected from Azoxystrobin, Benzovindiflupyr, Boscalid, Chlorothalonil, Cyclobutrifluram, Cyprodinil, Difenoconazole, Fluazinam, Fludioxonil, Hexaconazole, Isocycloseram, Isopyrazam, Mefentrifluconazole, Metalaxyl-M, Oxathiapiprolin, Prothioconazole, Pydiflumetofen, Pyraclostrobin, Spiropidion, and Tebuconazole; wherein component (B) and component (C) are not the same compound.

[0125] More preferably, component (A) is Feneptamidoquin, and components (B) and (C) are selected from Azoxystrobin, Benzovindiflupyr, Cyclobutrifluram, Cyprodinil, Difenoconazole, Fluazinam, Fludioxonil, Mefentrifluconazole, Oxathiapiprolin, Prothioconazole, Pydiflumetofen, Pyraclostrobin, and Tebuconazole; wherein component (B) and component (C) are not the same compound.

[0126] For instance, component (A) is Feneptamidoquin; component (B) is selected from Azoxystrobin, Benzovindiflupyr, Cyclobutrifluram, Cyprodinil, Mefentrifluconazole, Pydiflumetofen, and Tebuconazole; and component (C) is selected from Azoxystrobin, Difenoconazole, Fluazinam, Fludioxonil, Mefentrifluconazole, Metalaxyl-M, Oxathiapiprolin, Prothioconazole, and Pyraclostrobin; wherein component (B) and component (C) are not the same compound.

[0127] As examples, preferred compositions comprise as components (A), (B) and (C):• Feneptamidoquin, Azoxystrobin and Difenoconazole; or• Feneptamidoquin, Benzovindiflupyr and Azoxystrobin; or• Feneptamidoquin, Benzovindiflupyr and Prothioconazole; or• Feneptamidoquin, Cyclobutrifluram and Metalaxyl-M; or• Feneptamidoquin, Cyclobutrifluram and Oxathiapiprolin; or• Feneptamidoquin, Cyprodinil and Fludioxonil; or• Feneptamidoquin, Mefentrifluconazole and Azoxystrobin; or• Feneptamidoquin, Mefentrifluconazole and Pyraclostrobin; or• Feneptamidoquin, Pydiflumetofen and Azoxystrobin; or• Feneptamidoquin, Pydiflumetofen and Difenoconazole; or• Feneptamidoquin, Pydiflumetofen and Fluazinam; or• Feneptamidoquin, Pydiflumetofen and Mefentrifluconazole; or• Feneptamidoquin, Pydiflumetofen and Metalaxyl-M; or• Feneptamidoquin, Pydiflumetofen and Oxathiapiprolin; or• Feneptamidoquin, Pydiflumetofen and Prothioconazole; or109936 FF21• Feneptamidoquin, Tebuconazole and Prothioconazole.

[0128] Generally, the weight ratio of component (A) to the mixture of components (B) and (C) may be from 100:1 to 1 OO, or 50:1 to 1 :50, or 20:1 to 1 :20, or 10:1 to 1 :10, or 5:1 and 1 :5. Otherwise, the weight ratio of component (A) to the mixture of components (B) and (C) may be from 2:1 to 1 :2, or 4:1 to 2:1 , or 1 :1 , or 5:1 , or 5:2, or 5:3, or 5:4, or 4:1 , or 4:2, or 4:3, or 3:1 , or 3:2, or 2:1 , or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or 1 :600, or 1 :300, or 1 :150, or 1 :35, or 2:35, or 4:35, or 1 :75, or 2:75, or 4:75, or 1 :6000, or 1 :3000, or 1 :1500, or 1 :350, or 2:350, or 4:350, or 1 :750, or 2:750, or 4:750. Those mixing ratios are understood to include, on the one hand, ratios by weight and also, on other hand, molar ratios.

[0129] Examples of preferred compositions comprising Feneptamidoquin as component (A), a component (B) and a component (C) are given in Table T2 below:Table T2 Feneptamidoquin as component (A), in combination with components (B) and (C)

[0130] Fungicidal compositions comprising, as active ingredients, Feneptamidoquin as component (A) and a component (B) as mentioned above (binary compositions), and fungicidal compositions comprising, as active ingredients, Feneptamidoquin as component (A), a component (B) and a109936 FF22 component (C) as mentioned above (ternary compositions), may also be used for controlling phytopathogenic microorganism other than Phyllachora maydis, such as Venturia spp., Sclerotinia spp., Botrytis spp. and Fusarium spp. Venturia species include, for instance, Venturia inaequalis. Botrytis species include, for instance, Botrytis cinerea, Botryotinia aiiii, and Botryotinia fabae, Sclerotinia species include, for instance, Sclerotinia sclerotiorum and Sclerotinia minor. Fusarium species include, for instance, Fusarium acuminatum, Fusarium asiaticum, Fusarium avenaceum, Fusarium crookwellense, Fusarium culmorum, Fusarium graminearum (Gibberella zeae), Fusarium equiseti, Fusarium fujikoroi, Fusarium langsethiae, Fusarium musarum, Fusarium oxysporum, Fusarium oxysporum f.sp. cubense, Fusarium proliferatum, Fusarium poae, Fusarium pseudograminearum, Fusarium sambucinum, Fusarium scirpi, Fusarium semitectum, Fusarium solani, Fusarium sporotrichoides, Fusarium subglutinans, Fusarium tricinctum, Fusarium verticillioides, and Fusarium virguliforme.

[0131] Other examples of “reference” mixture compositions are as follows (wherein the term “TX” represents a compound (according to the definition of component (A) of the compositions of the present invention) selected from compound (I), compound (l-R), compound (l-S), and Feneptamidoquin, as defined in the Table X above):(4E,10Z)-tetradeca-4, 10-dienyl acetate + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate + TX, (E)- 6-methylhept-2-en-4-ol + TX, (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol + TX, (E)-tridec-4-en- 1-yl acetate + TX, (S)-bioallethrin + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadec-l 1-en-1-yl acetate + TX, (Z)-hexadec-l 1-enal + TX, (Z)-hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-icos-13-en- 10-one + TX, (Z)-tetradec-7-en-1-al + TX, (Z)-tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-yl acetate + TX, 1 ,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 1-(2-chlorophenyl)-3,3-dimethyl-2-(1 ,2,4-triazol- 1-ylmethyl)butan-2-ol + TX, 1-(5-bromo-2-pyridyl)-2-(2,4-difluorophenyl)-1 , 1 -difluoro-3-(1 ,2,4-triazol- 1-yl)propan-2-ol + TX, 1 -hydroxy-1 H-pyridine-2-thione + TX, 1 -methylcyclopropene + TX, 1- naphthaleneacetamide + TX, 1 -naphthylacetic acid + TX, 2,2-dichlorovinyl 2-ethylsu Ifinylethyl methyl phosphate + TX, 2,4-D + TX, 2,4-DB + TX, 2,6-dichloro-N-(4-trifluormethylbenzyl)benzamide + TX, 2- (1 , 3-d ithiolan-2-y l)phe ny I dimethylcarbamate + TX, 2-(2-butoxyethoxy)ethyl piperonylate + TX, 2-(4,5- dimethyl-1 ,3-dioxolan-2-yl)phenyl methylcarbamate + TX, 2-(difluoromethyl)-N-((3R)-1 ,1 ,3- trimethylindan-4-yl) pyridine-3-carboxamide + TX, 2-(octylthio)-ethanol + TX, 2-bromo-2- bromomethyl-pentanedinitrile + TX, 2-chlorovinyl diethyl phosphate + TX, 2-imidazolidone + TX, 2- methyl(prop-2-ynyl)aminophenyl methylcarbamate + TX, 2-thiocyanatoethyl laurate + TX, 3-(4- chlorophenyl)-5-methylrhodanine + TX, 3-(difluoromethyl)-1-methyl-N-[1 ,1 ,3-trimethylindan-4- yl]pyrazole-4-carboxamide + TX, 3-(difluoromethyl)-N-(7-fluoro-1 ,1 ,3,3-tetramethyl-indan-4-yl)-1- methyl-pyrazole-4-carboxamide + TX, 3-(difluoromethyl)-N-(7-fluoro-1 ,1 ,3,3-tetramethyl-indan-4-yl)- 1-methyl-pyrazole-4-carboxamide + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6- trifluorophenyl)pyridazine + TX, 3-methyl-1-phenylpyrazol-5-yl dimethyl-carbamate + TX, 3- phenylphenol + TX, 4,5-dichlorodithiol-3-one + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl- pyridazine-3-carbonitrile + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5- dimethyl-pyrazol-3-amine + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide + TX, 4-[[6-[2-(2,4-109936 FF23 difluorophenyl)-1 ,1-difluoro-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4- chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, 4-CPA + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate + TX, 4-methylnonan-5-ol with 4- methylnonan-5-one + TX, 4-phenylphenol + TX, 5-(1 ,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, 5-amino-1 ,3,4-thiadiazole-2-thiol + TX, 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine + TX, 5- hydroxy-6-methyl-4-(((E)-pyridin-3-ylmethylene)amino)-4,5-dihydro-1 ,2,4-triazin-3(2H)-one + TX, 5- methyl-6-thioxo-1 ,3,5-thiadiazinan-3-ylacetic acid + TX, 8-hydroxyquinoline sulfate + TX, 11-ethyl- 10,12-dioxo-2,5,8-trithia-4,11-diazatricyclo[7.3.0.03,7]dodeca-1 (9),3,6-triene-6-carbonitrile + TX, 14- methyloctadec-1-ene + TX, [(9Z,11 E)-tetradeca-9,11 -dienyl] acetate + TX, [(Z)-dodec-9-enyl] acetate + TX, abamectin + TX, acephate + TX, acequinocyl + TX, acetamiprid + TX, acethion + TX, acetoprole + TX, acibenzolar + TX, acibenzolar-S-methyl + TX, acrinathrin + TX, Adoxophyes orana GV + TX, Agrobacterium radiobacter + TX, alanycarb + TX, albendazole + TX, aldicarb + TX, allethrin + TX, allosamidin + TX, allyl alcohol + TX, allyxycarb + TX, alpha-ecdysone + TX, alpha-multistriatin + TX, Amblyseius spp. + TX, ametoctradin + TX, amidithion + TX, amidoflumet + TX, amidothioate + TX, aminocarb + TX, amisulbrom + TX, amiton + TX, amiton hydrogen oxalate + TX, amitraz + TX, anabasine + TX, Anagrapha falcifera NPV + TX, Anagrus atomus + TX, ancymidol + TX, anilazine + TX, anisiflupurin + TX, anthraquinone + TX, antu + TX, Aphelinus abdominalis + TX, Aphidius colemani + TX, Aphidoletes aphidimyza + TX, athidathion + TX, aureofungin + TX, Autographa californica NPV + TX, avermectin B1 a + TX, azaconazole + TX, azadirachtin A + TX, azafenidin + TX, azamethiphos + TX, azinphos-ethyl + TX, azinphos-methyl + TX, azithiram + TX, azoxystrobin + TX, Bacillus sphaericus (Neide) + TX, Bacillus thuringiensis + TX, Bacillus thuringiensis delta endotoxin + TX, Bacillus thuringiensis ssp. aizawai + TX, baculovirus + TX, barthrin + TX, Beauveria brong niartii + TX, benalaxyl + TX, benalaxyl-M + TX, benazepril + TX, benclothiaz + TX, benfuracarb + TX, benomyl + TX, bensultap + TX, benthiavalicarb + TX, benzalkonium chloride + TX, benzamorf + TX, benzothiostrobin + TX, benzovindiflupyr + TX, beta-cyfluthrin + TX, beta-cypermethrin + TX, bethoxazin + TX, bifemetstrobin + TX, bifenazate + TX, bifenthrin + TX, binapacryl + TX, bioallethrin + TX, bioethanomethrin + TX, biopermethrin + TX, bioresmethrin + TX, bisthiosemi + TX, bistrifluron + TX, bitertanol + TX, bixafen + TX, blasticidin-S + TX, borax + TX, bordeaux mixture + TX, boscalid + TX, brodifacoum + TX, brofenvalerate + TX, brofluthrinate + TX, bromadiolone + TX, bromfenvinfos + TX, bromophos + TX, bromophos-ethyl + TX, bromuconazole + TX, bufencarb + TX, bupirimate + TX, buprofezin + TX, buserelin + TX, busulfan + TX, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)- phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, butacarb + TX, butathiofos + TX, butocarboxim + TX, butonate + TX, butopyronoxyl + TX, butoxy(polypropylene glycol) + TX, butoxycarboxim + TX, butylamine + TX, cadusafos + TX, calciferol + TX, calcium phosphate + TX, calcium polysulfide + TX, cambendazole + TX, captafol + TX, captan + TX, carbanolate + TX, carbaryl + TX, carbendazim + TX, carbendazim hydrochloride + TX, carbofuran + TX, carbosulfan + TX, carboxin + TX, carprofen + TX, carpropamid + TX, cartap + TX, cartap hydrochloride + TX, cefalexin + TX, cefovecin + TX, cefquinome + TX, ceftiour + TX, cestex + TX, cevadine + TX, chinomethionat + TX, chitosan + TX, chlobenthiazone + TX, chloralose + TX, chlorantraniliprole + TX, chlorbenside +109936 FF24TX, chlordimeform + TX, chlorethephon + TX, chlorethoxyfos + TX, chlorfenapyr + TX, chlorfenazole + TX, chlorfentazine + TX, chlorfenvinphos + TX, chlorfluazuron + TX, chlormephos + TX, chlormequat + TX, chlorodimeform hydrochloride + TX, chloroinconazide + TX, chloromebuform + TX, chloromethiuron + TX, chloroneb + TX, chlorothalonil + TX, chlorphoxim + TX, chlorprazophos + TX, chlorpyrifos + TX, chlorpyrifos-methyl + TX, chlortetracycline + TX, chlorthiophos + TX, chlozolinate + TX, cholecalciferol + TX, chromafenozide + TX, Chrysoperla carnea + TX, cinerin + TX, cinerin I + TX, cinerin II + TX, cis-jasmone + TX, cis-resmethrin + TX, cismethrin + TX, clenbuterol + TX, climbazole + TX, cloethocarb + TX, clofencet + TX, clorsulon + TX, clothianidin + TX, clozylacon (acetamide) + TX, codlelure + TX, copper acetate + TX, copper hydroxide + TX, copper naphthenate + TX, copper octanoate + TX, copper oleate + TX, copper oxide + TX, copper oxychloride + TX, copper silicate + TX, copper sulfate + TX, copper(ll) carbonate + TX, coumachlor + TX, coumafene + TX, coumafuryl + TX, Coumatetralyl + TX, coumethoxystrobin (jiaxiangjunzhi) + TX, coumithoate + TX, coumoxystrobin + TX, cryolite + TX, Cryptolaemus montrouzieri + TX, cuelure + TX, cufraneb + TX, cuprous(l) oxide + TX, cyanofenphos + TX, cyanthoate + TX, cyazofamid + TX, cybutryne + TX, cyclafuramid + TX, cyclethrin + TX, cyclobutrifluram + TX, Cydia pomonella GV + TX, cyenopyrafen + TX, cyflufenamid + TX, cyflumetofen + TX, cyfluthrin + TX, cyhalothrin + TX, cymiazole + TX, cymoxanil + TX, cypermethrin (alphametrin) + TX, cyphenothrin + TX, cyproconazole + TX, cyprodinil + TX, cyprodinil + TX, cyromazine + TX, cytokinins + TX, D-tetramethrin + TX, Dacnusa sibirica + TX, DAEP + TX, dazomet + TX, DCPM + TX, debacarb + TX, decarbofuran + TX, deltamethrin + TX, demephion-O + TX, demephion-S + TX, demeton-O + TX, demeton-S + TX, demeton-S-methyl + TX, demeton-S-methylsulphon + TX, diafenthiuron + TX, dialifos + TX, diazinon + TX, dibutyl adipate + TX, dibutyl phthalate + TX, dibutyl succinate + TX, dicapthon + TX, dichlobentiazox + TX, dichlofluanid + TX, dichlone + TX, dichlorprop + TX, dichlorvos + TX, dichlozoline + TX, diclocymet + TX, diclomezine + TX, dicloran + TX, dicofol + TX, dicresyl + TX, dicrotophos + TX, dicyclanil + TX, dicyclopentadiene + TX, diethofencarb + TX, diethyltoluamide + TX, difenacoum + TX, difenoconazole + TX, difenzoquat + TX, difethialone + TX, diflovidazin + TX, diflubenzuron + TX, diflumetorim + TX, Diglyphus isaea + TX, dimatif + TX, dimefluthrin + TX, dimetan + TX, dimethachlon + TX, dimethipin + TX, dimethirimol + TX, dimethoate + TX, dimethomorph + TX, dimethrin + TX, dimethyl disulfide + TX, dimethyl phthalate + TX, dimetilan + TX, dimoxystrobin + TX, dinactin + TX, diniconazole + TX, diniconazole-M + TX, dinobuton + TX, dinocap + TX, dinocton + TX, dinoseb + TX, dinotefuran + TX, diofenolan + TX, dioxabenzofos + TX, diphenylamine + TX, dipyrithione + TX, disparlure + TX, disulfiram + TX, disulfoton + TX, ditalimfos + TX, dithianon + TX, dithicrofos + TX, dithiocarbamate + TX, dodec-8-en-1-yl acetate + TX, dodemorph + TX, dodicin + TX, dodine + TX, dofenapyn + TX, dominicalure + TX, doramectin + TX, drazoxolon + TX, DSP + TX, ecdysterone + TX, edifenphos + TX, emamectin benzoate + TX, EMPC + TX, empenthrin + TX, Encarsia formosa + TX, endosulfan + TX, endothal + TX, endothion + TX, enestroburin (enoxastrobin) + TX, enrofloxacin + TX, entomopathogenic bacteria + TX, entomopathogenic fungi + TX, entomopathogenic virus + TX, EPBP + TX, epoxiconazole + TX, eprinomectin + TX, Eretmocerus eremicus + TX, esfenvalerate + TX, etaconazole + TX, ethaboxam + TX, ethiofencarb + TX, ethion + TX, ethiprole + TX, ethirimol + TX,109936 FF25 ethoate-methyl + TX, ethoprophos + TX, ethoxyquin + TX, ethyl 4-methyloctanoate + TX, ethyl formate + TX, ethyl hexanediol + TX, etofenprox + TX, etoxazole + TX, etridiazole + TX, etrimfos + TX, eugenol + TX, eurax + TX, EXD + TX, exo-brevicomin + TX, famoxadone + TX, famphur + TX, farnesol with nerolidol + TX, febantel + TX, fenamidone + TX, fenaminstrobin + TX, fenamiphos + TX, fenarimol + TX, fenazaquin + TX, fenbendazole + TX, fenbuconazole + TX, fenbutatin oxide + TX, fenethacarb + TX, fenfluthrin + TX, fenfuram + TX, fenhexamid + TX, fenitrothion + TX, fenobucarb + TX, fenopyramid + TX, fenothiocarb + TX, fenoxacrim + TX, fenoxanil + TX, fenoxycarb + TX, fenpiclonil + TX, fenpicoxamid + TX, fenpirithrin + TX, fenpropathrin + TX, fenpropidin + TX, fenpropimorph + TX, fenpyrazamine + TX, fenpyroximate + TX, fensulfothion + TX, fenthion + TX, fenthion-ethyl + TX, fentin + TX, fentin acetate + TX, fentin chloride + TX, fentin hydroxide + TX, fenvalerate + TX, ferbam + TX, ferimzone + TX, ferric phosphate + TX, fipronil + TX, flocoumafen + TX, flonicamid + TX, florfenicol + TX, florylpicoxamid + TX, fluacrypyrim + TX, fluazinam + TX, fluazuron + TX, flubendazole + TX, flubendiamide + TX, flubeneteram + TX, flubenzimin + TX, flucycloxuron + TX, flucycloxuron + TX, flucythrinate + TX, fludioxonil + TX, fluenetil + TX, flufenerim + TX, flufenoxuron + TX, flufenoxystrobin + TX, flufenprox + TX, fluindapyr + TX, flumetralin + TX, flumetylsulforim + TX, flumorph + TX, fluopicolide + TX, fluopimomide + TX, fluopyram + TX, fluoroimide + TX, fluoxapiprolin + TX, fluoxastrobin + TX, fluoxytioconazole + TX, flupyrazofos + TX, fluquinconazole + TX, flusilazole + TX, flusulfamide + TX, flutianil + TX, flutolanil + TX, flutriafol + TX, fluxapyroxad + TX, folpet + TX, fonofos + TX, forchlorfenuron + TX, formaldehyde + TX, formetanate + TX, formetanate hydrochloride + TX, formothion + TX, formparanate + TX, fosetyl + TX, fosetyl-aluminium + TX, fosmethilan + TX, fosthiazate + TX, fosthietan + TX, frontalin + TX, fuberidazole + TX, furalaxyl + TX, furametpyr + TX, furathiocarb + TX, furethrin + TX, furfural + TX, gibberellic acid + TX, glyodin + TX, glyphosate + TX, grandlure I + TX, grandlure II + TX, grandlure III + TX, grandlure IV + TX, guazatine triacetate + TX, halfenprox + TX, halofenozide + TX, hemel + TX, heptenophos + TX, Heterorhabditis bacteriophora and H. megidis + TX, hexaconazole + TX, hexadecyl cyclopropanecarboxylate + TX, hexaflumuron + TX, hexalure + TX, hexamide + TX, hexythiazox + TX, Hippodamia convergens + TX, huanjunzuo (rac-(1 S,2S)-1-(4-chlorophenyl)-2-(1 ,2,4-triazol-1-yl)cycloheptanol) + TX, hydramethylnon + TX, hydrated lime (calcium hydroxide) + TX, hymexazol + TX, hyquincarb + TX, icaridin + TX, imanin (hypericin) + TX, imazalil + TX, imazalil sulfate + TX, imibenconazole + TX, imidacloprid + TX, iminoctadine + TX, indoxacarb + TX, inpyrfluxam + TX, iodocarb + TX, ipconazole + TX, ipfentrifluconazole + TX, ipflufenoquin + TX, iprobenfos (IBP) + TX, iprodione + TX, iprovalicarb + TX, ipsdienol + TX, ipsenol + TX, IPSP + TX, isamidofos + TX, isazofos + TX, isocarbophos + TX, isofetamid + TX, isoflucypram + TX, isolan + TX, isoprocarb + TX, isoprothiolane + TX, isopyrazam + TX, isothioate + TX, isotianil + TX, isoxathion + TX, ivermectin + TX, japonilure + TX, jasmolin I + TX, jasmolin II + TX, juvenile hormone I + TX, juvenile hormone II + TX, juvenile hormone III + TX, kadethrin + TX, kanamycin + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, kinetin + TX, kinoprene + TX, kresoxim-methyl + TX, kurstaki + TX, lambda-cyhalothrin + TX, Leptomastix dactylopii + TX, leptophos + TX, levamisole + TX, lineatin + TX, lirimfos + TX, looplure + TX, lufenuron + TX, Ivbenmixianan + TX, lythidathion + TX, m-cumenyl methylcarbamate + TX, Macrolophus109936 FF26 caliginosus + TX, magnesium phosphide + TX, malathion + TX, maleic hydrazide + TX, malonoben + TX, Mamestra brassicae NPV + TX, mancopper + TX, mancozeb + TX, mandestrobin + TX, mandipropamid + TX, maneb + TX, mazidox + TX, mebendazole + TX, mecarbam + TX, mecarphon + TX, medlure + TX, mefentrifluconazole + TX, megatomoic acid + TX, meloxicam + TX, menazon + TX, mepanipyrim + TX, meperfluthrin + TX, mephosfolan + TX, mepiquat + TX, mepronil + TX, meptyldinocap + TX, mesulfenfos + TX, metaflumizone + TX, metalaxyl + TX, metalaxyl-M + TX, metaldehyde + TX, metam + TX, metam-potassium + TX, metam-sodium + TX, Metaphycus helvolus + TX, Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, metarylpicoxamid + TX, metconazole + TX, methacrifos + TX, methamidophos + TX, methasulfocarb + TX, methidathion + TX, methiocarb + TX, methiotepa + TX, methocrotophos + TX, methomyl + TX, methoprene + TX, methoquin-butyl + TX, methothrin + TX, methoxyfenozide + TX, methyl apholate + TX, methyl eugenol + TX, methyl iodide + TX, methyl neodecanamide + TX, metiram + TX, metofluthrin + TX, metolcarb + TX, metominostrobin + TX, metoxadiazone + TX, metrafenone + TX, metyltetraprole + TX, mevinphos + TX, mexacarbate + TX, MGK 264 + TX, milbemycin + TX, milbemycin oxime + TX, monocrotophos + TX, morantel tartrate + TX, morzid + TX, moxidectin + TX, muscalure + TX, myclobutanil + TX, myclozolin + TX, Myrothecium verrucaria composition + TX, N- [2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, N- cyclopropyl-3-(difluoromethyl)-5-fluoro-N-[(2-isopropylphenyl)methyl]-1-methyl-pyrazole-4- carboxamide + TX, nabam + TX, naled + TX, NC-170 + TX, nemadectin + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, niclosamide-olamine + TX, nicotine + TX, nicotine sulfate + TX, nikkomycins + TX, nitenpyram + TX, nithiazine + TX, nitrapyrin + TX, nitrilacarb + TX, nitrothal- isopropyl + TX, norbormide + TX, nornicotine + TX, novaluron + TX, noviflumuron + TX, nuarimol + TX, 0,0,0',0'-tetrapropyl dithiopyrophosphate + TX, octadeca-2,13-dien-1-yl acetate + TX, octadeca- 2, 13-dien-1 -yl acetate + TX, octhilinone + TX, ofurace + TX, oleic acid + TX, omethoate + TX, orfralure + TX, Orius spp. + TX, orysastrobin + TX, osthol + TX, ostramone + TX, oxadixyl + TX, oxamate + TX, oxamyl + TX, oxantel pamoate + TX, oxasulfuron + TX, oxathiapiprolin + TX, oxfendazole + TX, oxibendazole + TX, oxine copper + TX, oxolinic acid + TX, oxpoconazole + TX, oxycarboxin + TX, oxydemeton-methyl + TX, oxydeprofos + TX, oxydisulfoton + TX, oxytetracycline + TX, oxytetracycline dihydrate + TX, paclobutrazol + TX, Paecilomyces fumosoroseus + TX, paraoxon + TX, parathion + TX, parathion-methyl + TX, parbendazole + TX, pefurazoate + TX, penconazole + TX, pencycuron + TX, penethamate + TX, penflufen + TX, penthiopyrad + TX, permethrin + TX, petroleum oils + TX, PH 60-38 + TX, phenamacril + TX, phenthoate + TX, phorate + TX, phosacetim + TX, phosalone + TX, phosfolan + TX, phosglycin + TX, phosmet + TX, phosnichlor + TX, phosphamidon + TX, phosphocarb + TX, phosphonic acid + TX, phosphorus + TX, phoxim + TX, phoxim-methyl + TX, phthalide + TX, Phytoseiulus persimilis + TX, picarbutrazox + TX, picoxystrobin + TX, pimobendan + TX, pindone + TX, piperalin + TX, piperonyl butoxide + TX, piprotal + TX, pirimetaphos + TX, pirimicarb + TX, pirimiphos-methyl + TX, polycarbamate + TX, polynactin + TX, polyoxin B + TX, polyoxin d + TX, potassium ethylxanthate + TX, potassium hydroxyquinoline sulfate + TX, praziquantel + TX, precocene I + TX, precocene II + TX, precocene III + TX, primidophos + TX, probenazole + TX,109936 FF27 prochloraz + TX, procymidone + TX, profenofos + TX, profluthrin + TX, prohexadione + TX, prohexadione-calcium + TX, promacyl + TX, promecarb + TX, propamidine + TX, propamocarb + TX, propaphos + TX, propargite + TX, propetamphos + TX, propiconazole + TX, propineb + TX, propionic acid + TX, propoxur + TX, propyl isomer + TX, proquinazid + TX, prothidathion + TX, prothioconazole + TX, prothiofos + TX, prothoate + TX, protrifenbute + TX, pydiflumetofen + TX, pymetrozine + TX, pyraclofos + TX, pyraclostrobin + TX, pyrafluprole + TX, pyrametostrobin + TX, pyrantel pamoate + TX, pyraoxystrobin + TX, pyrapropoyne + TX, pyraziflumid + TX, pyrazophos + TX, pyrazoxone + TX, pyresmethrin + TX, pyrethrin I + TX, pyrethrin II + TX, pyrethrins (natural products) + TX, pyrethroids (natural products) + TX, pyribencarb + TX, pyridaben + TX, pyridachlometyl + TX, pyridalyl + TX, pyridaphenthion + TX, pyridin-4-amine + TX, pyrifenox + TX, pyrifluquinazon + TX, pyrimethanil + TX, pyrimidifen + TX, pyrimorph + TX, pyriofenone + TX, pyriprole + TX, pyriproxyfen + TX, pyrisoxazole + TX, pyroquilon + TX, quassia + TX, quinalphos + TX, quinalphos-methyl + TX, quinoclamine + TX, quinofumelin + TX, quinonamid + TX, quinothion + TX, quinoxyfen + TX, quintozene + TX, R-1492 + TX, R-metalaxyl + TX, Reynoutria sachalinensis extract + TX, ribavirin + TX, rotenone + TX, ryanodine (ryania) + TX, sabadilla + TX, schradan + TX, scilliroside + TX, seboctylamine + TX, sedaxane + TX, selamectin + TX, sesamex + TX, sesamolin + TX, siglure + TX, silafluofen + TX, silthiofam + TX, simeconazole + TX, sodium tetrathiocarbonate + TX, sophamide + TX, sordidin + TX, spinetoram + TX, spinosad + TX, spirodiclofen + TX, spiromesifen + TX, spirotetramat + TX, spiroxamine + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisci + TX, Steinernema spp. + TX, streptomycin + TX, streptomycin sesquisulfate + TX, sulcatol + TX, sulcofuron + TX, sulfiram + TX, sulfur + TX, sulprofos + TX, tar oils + TX, tau-fluvalinate + TX, TCMTB + TX, TDE + TX, tebuconazole + TX, tebufenozide + TX, tebufenpyrad + TX, tebufloquin + TX, tebupirimfos + TX, tecnazene + TX, teflubenzuron + TX, tefluthrin + TX, temephos + TX, terallethrin + TX, terbam + TX, terbufos + TX, tetrachlorvinphos + TX, tetraconazole + TX, tetradec-11-en-1-yl acetate + TX, tetradifon + TX, tetramethrin + TX, tetramethylfluthrin + TX, tetranactin + TX, thiabendazole + TX, thiacloprid + TX, thiadiazole copper + TX, thiamethoxam + TX, thiapronil + TX, thicrofos + TX, thicyofen + TX, thidiazuron + TX, thifluzamide + TX, thiocarboxime + TX, thiocyclam + TX, thiocyclam hydrogen oxalate + TX, thiodicarb + TX, thiofanox + TX, thiometon + TX, thiophanate + TX, thiophanate-methyl + TX, thioquinox + TX, thiosultap + TX, thiosultap-disodium + TX, thiram + TX, thuringiensin + TX, tiadinil + TX, tiamulin + TX, tioxymid + TX, tolclofos-methyl + TX, tolfenpyrad + TX, tolprocarb + TX, tolylfluanid + TX, tralomethrin + TX, transpermethrin + TX, tretamine + TX, triadimefon + TX, triadimenol + TX, triarathene + TX, triazamate + TX, triazophos + TX, triazoxide + TX, tribufos + TX, trichlorfon + TX, trichlormetaphos-3 + TX, trichloronat + TX, Trichogramma spp. + TX, triclabendazole + TX, triclopyricarb + TX, tricyclazole + TX, tridemorph + TX, trifenmorph + TX, trifloxystrobin + TX, triflumizole + TX, triflumuron + TX, triforine + TX, trimedlure + TX, trimedlure A + TX, trimedlure B1 + TX, trimedlure B2 + TX, trimedlure C + TX, trimethacarb + TX, trinactin + TX, trinexapac + TX, trinexapac-ethyl + TX, trioxyflanilide + TX, triprene + TX, triticonazole + TX, trunc- call + TX, tulathromycin + TX, Typhlodromus occidentalis + TX, uniconazole + TX, uredepa + TX,109936 FF28 validamycin + TX, valifenalate + TX, vamidothion + TX, vaniliprole + TX, veratridine + TX, veratrine + TX, verbutin + TX, Verticillium lecanii + TX, vinclozolin + TX, XMC + TX, xylenols + TX, zeatin + TX, zeta-cypermethrin + TX, zhongshengmycin + TX, zinc naphthenate + TX, zinc thiazole + TX, zineb + TX, ziram + TX, zolaprofos + TX, zoxamide +TX.

[0132] The references in brackets behind the active ingredients, e.g. [3878-19-1] refer to the Chemical Abstracts Registry number. The above described mixing partners are known. Where the active ingredients are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C. D. S. TomLin; The British Crop Protection Council], they are described therein under the entry number given in round brackets hereinabove for the particular compound; for example, the compound "abamectin" is described under entry number (1). Where "[CCN]" is added hereinabove to the particular compound, the compound in question is included in the "Compendium of Pesticide Common Names", which is accessible on the internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; for example, the compound "acetoprole" is described under the internet address http: / / www.alanwood.net / pesticides / acetoprole.html

[0133] Most of the active ingredients described above are referred to hereinabove by a so-called "common name", the relevant "ISO common name" or another "common name" being used in individual cases. If the designation is not a "common name", the nature of the designation used instead is given in round brackets for the particular compound; in that case, the IUPAC name, the lUPAC / Chemical Abstracts name, a "chemical name", a "traditional name", a "compound name" or a "development code" is used or, if neither one of those designations nor a "common name" is used, an "alternative name" is employed. “CAS Reg. No” means the Chemical Abstracts Registry Number.

[0134] In the “reference” mixture compositions the mixtures of compounds selected from Table X (above) with active ingredients described above comprise a compound selected from Table X (above) and an active ingredient as described above preferably in a mixing ratio of from 100:1 to 1 :100, especially from 50:1 to 1 :50, more especially in a ratio of from 20:1 to 1 :20, even more especially from 10:1 to 1 :10, very especially from 5:1 and 1 :5, special preference being given to a ratio of from 2:1 to 1 :2, and a ratio of from 4:1 to 2:1 being likewise preferred, above all in a ratio of 1 :1 , or 5:1 , or 5:2, or 5:3, or 5:4, or 4:1 , or 4:2, or 4:3, or 3:1 , or 3:2, or 2:1 , or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or 1 :600, or 1 :300, or 1 :150, or 1 :35, or 2:35, or 4:35, or 1 :75, or 2:75, or 4:75, or 1 :6000, or 1 :3000, or 1 :1500, or 1 :350, or 2:350, or 4:350, or 1 :750, or 2:750, or 4:750. Those mixing ratios are by weight.

[0135] The mixture compositions as described above (both according to the invention and the “reference” mixture compositions) can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the pests or their environment.

[0136] The mixtures comprising a compound selected from Table X (above) and one or more active ingredients as described above can be applied, for example, in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a “tank-mix”, and in a combined use of the single active ingredients when109936 FF29 applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. The order of applying the compounds selected from Table X (above) and the active ingredients as described above is not essential for working the present invention.Biological examplesExperimental - Example 1 :

[0137] A single fungicide foliar application was made to dent corn, variety Croplan 3899, at approximately stage R1 in an application volume of 15 gallons / acre (about 140 L / ha). This corn had been planted about 2 months and 10 days before in Wisconsin. Weather conditions were highly conducive for Phyllochora maydis development. The first visual symptoms were observed 22 days after last application (DALA). Disease severity continued to increase over the season with the final assessment taken 56 days after last application. This trial contained the following treatments: A = untreated control, B = Trivapro® at 265 g ai / ha, C = Compound l-A at 100 g ai / ha, D = Compound l-A at 200 g ai / ha, and E = Tilt® at 125 g ai / ha. All fungicides were applied with a non-ionic surfactant at 0.125%v / v. Data were analyzed using LSD (alpha value 0.05). Compound l-A was Feneptamidoquin.

[0138] Trivapro® is a commercial fungicide product containing Propiconazole, Azoxystrobin and Benzofindiflupyr as active ingredients. According to its label, Trivapro® may be used to control various fungal phytopathogens, including Tar spot (Phyllachora maydis) on Corn.

[0139] Propiconazole is a triazole fungicide, in FRAC (Fungicide Resistance Action Committee, 2024) Group 3. Azoxystrobin is a strobilurin fungicide in FRAC Group 11. Benzofindiflupyr is a succinate dehydrogenase inhibitor in FRAC Group 7.

[0140] Tilt® is a commercial fungicide product containing Propiconazole as active ingredient. It is a broad sprectrum fungicide. According to the label of Tilt®, this product is not known to control Tar spot.

[0141] Results of the trial are shown on Figure 1. Disease severity was assessed 22, 46 and 56 days after last application (i.e. after stage R1).

[0142] The best treatments in this trial were both rates of Compound l-A. These treatments resulted in disease severity significantly less than the untreated control and all the other fungicides included in this trial.

[0143] These results also suggest that Compound l-A (Feneptamidoquin) may be useful in the control of strains of fungal phytopathogens, such as Phyllachora maydis, which exhibit resistance to fungicides selected from FRAC Group 3 fungicides, FRAC Group 7 fungicides and / or FRAC Group 11 fungicides.

[0144] These results also suggest that Compound l-A may be integrated into treatment rotations, to manage potential resistance of plant pathogens.

[0145] Leaf senescence was also observed in this trial. Results are shown with Figure 2. Again, the best treatments were both rates of Compound l-A. These treatments resulted in significantly less leaf senescence than was observed in the untreated control (A) and in the other fungicides included in this trial, as shown with Figure 2.109936 FF30Experimental - Example 2 - Comparison with other DHODH inhibitors:

[0146] In a similar trial, the efficacy of Feneptamidoquin on Corn Tar Spot was compared to that of other DHODH inhibitors, namely Ipflufenoquin and Quinofumelin. Plots had a surface of 12 m2. Each treatment was repeated 4 times. A single fungicide foliar application was made to dent corn, variety 53-60 Dekalb, at approximately stage BBCH 61 in an application volume of 10.7 gallons / acre (100 L / ha). This trial was conducted in Ontario, Canada. Weather conditions were highly conducive for Phyllochora maydis development. The first visual symptoms were observed 12 days after the application (DAA). Disease severity continued to increase over the season with the final assessment taken 51 days after the application. This trial contained the following treatments: A = untreated control, B = Feneptamidoquin at 125 g ai / ha, C = Ipfludenoquin 125 g ai / ha, and D = Quinofemelin at 125 g ai / ha. All fungicides were applied with a non-ionic surfactant at 0.125%v / v. Data were analyzed using LSD (alpha value 0.05).

[0147] Results are shown in Figure 3:A = untreated controlB = Feneptamidoquin at 125 g ai / ha + non-ionic surfactant at 0.125%v / vC = Ipflufenoquin at 125 g ai / ha + non-ionic surfactant at 0.125%v / v D = Quinofumelin at 125 g ai / ha + non-ionic surfactant at 0.125%v / v

[0148] In this trial at 38 DAA, the treatment with Feneptamidoquin (B) results in less than 10% of the leaf area being affected, while Ipflufenoquin and Quinofumelin exhibit 25% to 30% of affected leaf area.Experimental - Example 3:

[0149] In anothertrial, the efficacy of Feneptamidoquin on Corn Tar Spot was compared to Miravis® Neo and an untreated control. Miravis® Neo is a broad-spectrum fungicidal suspension concentrate (SC) which contains 75 g / L of Pydiflumetofen, 100 g / L of Azoxystrobine and 125 g / L of Propiconazole. Plots had a surface of 12 m2. Each treatment was repeated 4 times. Disease severity was assessed 38 days after the application (DAA), as the percentage of affected leaf area. The higher the number is, the more severe the disease is. Plant senescence was assessed at 54 DAA, as a percentage of the entire plant. The higher the percentage is, the more of the plant has senesced.

[0150] A single fungicide foliar application was made to dent corn, variety 53-60 Dekalb, at approximately stage BBCH 61 in an application volume of 21.4 gallons / acre (200 L / ha). This trial was conducted in Ontario Canada. Weather conditions were highly conducive for Phyllochora maydis development. The first visual symptoms were observed 14 days after the application (DAA). Disease severity continued to increase over the season with the final assessment taken 53 days after the application. A percent leaf senescence rating was also taken 54 DAA. This trial contained the following treatments: A = untreated control, B = Feneptamidoquin at 125 g ai / ha, and C = Miravis® Neo at 375 g ai / ha. All fungicides were applied with a non-ionic surfactant at 0.125%v / v. Data were analyzed using LSD (alpha value 0.05).

[0151] Results are shown in Figure 4:A = untreated control109936 FF31B = Feneptamidoquin at 125 g ai / ha + non-ionic surfactant at 0.125%v / vC = Miravis® Neo at 375 g ai / ha + non-ionic surfactant at 0.125%v / v

[0152] In this trial at 40 DAA, the treatment with Feneptamidoquin (B) resulted in 13.3% of the leaf area being affected, while the untreated control (A) and Miravis® Neo (C) exhibited 68.8% and 19.3% of affected leaf area respectively.

[0153] Results are shown in Figure 5:A = untreated controlB = Feneptamidoquin at 125 g ai / ha + non-ionic surfactant at 0.125%v / vC = Miravis® Neo at 375 g ai / ha + non-ionic surfactant at 0.125%v / v

[0154] In this trial at 55 DAA, the treatment of Feneptamidoquin (B) resulted in 62.5% of the plant area showing senescence, while the untreated control (A) and Miravis® Neo (C) exhibited 95.8% and 68.3% of the plant area showing senescence respectively.REFERENCES

[0155] Ruhl et al., 2016, Plant Diseases 100(7):1496, First Report of Tar Spot on Corn Caused by Phyllachora maydis in the United States

[0156] Valle-Torres et al., 2020, Plant Diseases 104(10):2541-50, Tar Spot: An Understudied Disease Threatening Corn Production in the Americas

[0157] Solorzano et al., 2023, Plant Methods 19:83, A new and effective method to induce infection of Phyllachora maydis into corn for tar spot studies in controlled environments

[0158] Ritchie et al., 1986, How a corn plant develops. Iowa State University of Science and Technology Cooperative Extension. Ames, Iowa.

Claims

109936 FF32CLAIMS1. A method of controlling or preventing infestation of plants by the phytopathogenic microorganism Phyllachora maydis comprising applying to the phytopathogen, to the locus of the phytopathogen, or to a plant susceptible to attack by the phytopathogen, or to a propagation material thereof, a fungicidally effective amount of the compound of formula (I)(I).

2. The method according to claim 1 wherein the compound of formula (I) is selected from compound of formula (l-R), compound of formula (l-S) and combinations thereof:

3. A method according to either claim 1 or claim 2, wherein the compound of formula (I) is compound of formula (l-R):109936 FF334. A method according to either claim 1 or claim 2, wherein the compound of formula (I) is compound of formula (l-S):

5. A method according to claim 2, wherein the compound of formula (I) is a combination of compound of formula (l-R) and compound of formula (l-S), in a molar ratio (l-R) : (l-S) greater than 1.5 : 1 , greater than 2.5 : 1 , greater than 4 : 1 , or greater than 9 : 1.

6. The use of a compound of formula (I) as defined in any one of claims 1 to 5 for controlling or preventing infestation of plants by the phytopathogenic microorganism Phyllachora maydis.

7. The use of a compound of formula (I) as defined in any one of claims 1 to 5 for controlling or preventing leaf senescence of cultivated plants.

8. The use according to claim 7, where said cultivated plant is infected by the phytopathogenic microorganism Phyllachora maydis.

9. The method or use according to any one of claims 1 to 8 wherein the plant is corn or maize Zea mays.

10. The method or use according to any one of claims 1 to 9, wherein the compound of formula(I) is feneptamidoquin.

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