Method of pathogen control in soybean

Abstract

The present invention relates to a method of combating, preventing or controlling Diaporthe species, which comprises applying to a crop of soybean, the locus thereof, or propagation material thereof, a compound of formula (I) wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts or N-oxides of those compounds, or a composition comprising the compound of formula (I).

Description

[0001] METHOD OF PATHOGEN CONTROL IN SOYBEAN

[0002] The present invention relates to a method of pathogen control in soybean crops. In particular, it relates to a method of combating, preventing or controlling Diaporthe species, by applying to a crop of soybean, the locus thereof, or propagation material thereof, a compound of formula (I), and to the use of said compound.

[0003] Diaporthe spp. are responsible for diseases on a wide range of plants hosts, some of which are economically important worldwide, causing root and fruit rots, dieback, cankers, leaf spots, blights, decay and wilt (Uecker, F. A. A “World list of Phomopsis names with notes on nomenclature, -morphology and biology” Mycological Memoirs 1988, 13, 1-231 ). Species of Diaporthe and their Phomopsis asexual states have broad host ranges and are widely distributed. In soybean, four distinct but closely related species are known to infect and form species complex namely, Diaporthe phaseolorum var sojae, Diaporthe phaseolorum var caulivora, Diaporthe aspalathi and P. longicolla (PIOLI, Rosanna N., et al. “Morphologic, molecular, and pathogenic characterization of Diaporthe phaseolorum variability in the core soybeanproducing area of Argentina” Phytopathology 2003, 93 (2), 136-146; Santos, J. M., et al. “Resolving the Diaporthe species occurring on soybean in Croatia” Persoonia-Molecular Phylogeny and Evolution of Fungi 2011 , 27 (1 ), 9-19).

[0004] Diaporthe is a large and taxonomically complex genus, with over a thousand epithets listed in Index Fungorum. The placement of many Diaporthe species remains confusing, and there is a lack of consensus on their taxonomy and phylogeny (Hongsanan S et al. Mycosphere 2023, 14(1), 918-1189), Hongsanan S et al. provide in their report an overview of the 832 species and include information on their morphology, ecology, geographic distribution, molecular data, and pathogenicity, where available.

[0005] Diaporthe species comprise pathogens, endophytes, and saprobes, and are associated with a wide range of hosts (Dissanayake et al. 2017a, Bhunjun et al. 2022).

[0006] Several species in this genus have been reported as pathogens of economically important plants and can cause various plant diseases, such as diebacks, cankers, leaf spots, blights, melanoses, stem-end rot, and gummosis, affecting diverse hosts such as soybeans, peanuts, sunflower, grapevine, and citrus.

[0007] During the 2021 / 2022 soybean season in Brazil, farmers faced an increase in soybean breakage, with consequent lodging and toppling of plants. Despite their best efforts, farmers watched helplessly as pods split and seeds decayed on growing crops. Losses were high, up to 70%, particularly in the country’s agricultural heartland of Mato Grosso, where nearly half the entire crop was destroyed.

[0008] Given the economic significance of this disease, there was a need to identify the cause of the yield loss. Samples have been taken, and isolates confirmed the presence of genera from the Diaporthe spp., in particular wherein said Diaporthe spp. is selected from Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, or combinations thereof.

[0009] Diaporthe miriciae and Diaporthe masirevicii have been isolated previously as endophytes or pathogens causing leaf spots, fruit rots and dieback in various plant species (Thompson, S.M. et al. Plant Disease 2018, 102, 1459; Dong et al. Frontiers in Microbiology 2021 , 11 , 609387; Hongsanan et al. Mycosphere 2023, 14, 918-1189). Recently, Diaporthe miriciae was reported as the causal agent of soybean stem canker in Colombia (Lopez-Cardona et al. Plant Disease 2021 , 105, 4162). There exists a need for the development of new methods for controlling or preventing infestation by the phytopathogenic fungi, especially fungi such as Diaporthe species.

[0010] There exists further a need for a method of controlling or preventing an infestation of plants, e.g., useful plants such as crop plants, propagation material thereof, e.g., seeds, harvested crops, e.g., harvested food crops, or of non-living materials by Diaporthe spp., which comprises the application of a compound of formula (I) according to the invention, as defined herein 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.

[0011] It has been surprisingly found that compounds, as disclosed in WO2019 / 173665, are highly effective at controlling or preventing the infestation of crops by the phytopathogenic microorganisms of the family Diaporthe species, also known as Phomopsis species. These highly effective compounds thus represent an important new solution for farmers to control or prevent infestation of crops by the phytopathogenic microorganism Diaporthe spp.

[0012] Further it has been surprisingly found that particular compounds as disclosed in WO2019 / 173665, are highly effective at controlling or preventing the infestation of soybean by the phytopathogenic microorganisms of the family Diaporthe. These highly effective compounds thus represent an important new solution for farmers to control or prevent infestation of soybean by the phytopathogenic microorganism Diaporthe spp.

[0013] Additionally, it has now been surprisingly found that particular compounds disclosed in WO2019 / 173665, are highly effective at controlling or preventing the infestation of genetically modified soybean by the phytopathogenic microorganisms of the family Diaporthe. These highly effective compounds thus represent an important new solution for farmers to control or prevent infestation of genetically modified soybean, like Bt soybean, by the phytopathogenic microorganism Diaporthe spp.

[0014] According to a first aspect of the present invention, there is provided a method of controlling or preventing infestation of soybeans by the phytopathogenic microorganism Diaporthe species, comprising applying to a crop of soybean, the locus thereof, or propagation material thereof, a fungicidally effective amount of a compound according to formula (I) ([(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy-3- propanoyloxy-pyridine-2-carbonyl)amino] propanoate)

[0015] (I).

[0016] Said compounds, their pesticidal action and suitable methods for producing are disclosed in WO2019 / 173665.

[0017] According to a second aspect of the present invention, there is provided a method of controlling or preventing infestation of crops by the phytopathogenic microorganism Diaporthe species, comprising applying to a crop of soybean, the locus thereof, or propagation material thereof, a pesticidal composition comprising the compound of formula (I), and one or more formulation adjuvants.

[0018] According to a third aspect of the present invention, there is provided the use of the compound of formula (I) for controlling or preventing infestation of soybean by the phytopathogenic microorganism Diaporthe species.

[0019] According to another aspect of the present invention, there is provided a method of controlling or preventing infestation of soybeans by the phytopathogenic microorganism Diaporthe species, comprising applying to a crop of soybean, the locus thereof, or propagation material thereof, a fungicidally effective amount of [(1S,2S)-1-methyl-2-(o-tolyl)propyl]-(2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino] propanoate according to formula (I): or an agrochemically acceptable salt, or N-oxide thereof, wherein said soybeans are genetically modified soybeans, preferably Bt soybeans.

[0020] According to another of the present invention, the present invention relates to a pesticidal composition suitable for control of diseases caused by phytopathogenic microorganism Diaporthe species, a soybean, the locus thereof, or propagation material thereof, comprising a component (A) and at least one or more compound(s) (B), wherein said component A is [(1 S,2S)-1-methyl-2-(o-tolyl)propyl]-(2S)-2-[(4-methoxy-3- propanoyloxy-pyridine-2-carbonyl)amino] propanoate according to formula (I), and wherein said at least one or more compound(s) (B) is selected from other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides, one or more adjuvant(s), and a diluent or carrier.

[0021] In a preferred embodiment of the present invention, there is provided a method of controlling or preventing infestation of soybeans by the phytopathogenic microorganism Diaporthe species, comprising applying to a crop of soybean, the locus thereof, or propagation material thereof, a fungicidally effective amount of [(1S,2S)-1-methyl-2-(o-tolyl)propyl]-(2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino] propanoate according to formula (I), wherein said Diaporthe spp. is selected from Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, or combinations thereof.

[0022] According to another of the present invention, the present invention relates to a pesticidal composition suitable for control of diseases caused by phytopathogenic microorganism Diaporthe species, a soybean, the locus thereof, or propagation material thereof, comprising a component (A) and at least one or more compound(s) (B), wherein said component A is [(1 S,2S)-1 -methy l-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy-3- propanoyloxy-pyridine-2-carbonyl)amino] propanoate according to formula (I), wherein said at least one or more compound(s) (B) is selected from other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides, one or more adjuvant(s), and a diluent or carrier; and wherein said Diaporthe spp. is selected from Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, or combinations thereof.

[0023] As used herein, the term “genetically modified plants” refer to plants, that are the products of using recombinant DNA techniques in plant breeding. Recombinant DNA techniques, also known as genetic engineering or genetic modification, refer to the modification of an organism's genetic make-up using transgenesis, in which DNA from one organism or cell (the transgene) is transferred to another without sexual reproduction. Genetically modified organisms (GMOs) are modified by the application of transgenesis or recombinant DNA technology, in which a transgene is incorporated into the host genome or a gene in the host genome is modified to change its level of expression. The term “genetically modified” can be used interchangeably with “transgenic” or “genetically engineered”. The term genetically modified plants” can be used interchangeably with “genetically modified crops”.

[0024] As used herein, the term "controlling" refers to reducing the number of pests, eliminating pests and / or preventing further pest damage such that damage to a plant or to a plant derived product is reduced.

[0025] As used herein, the term "pest" refers to insects, and molluscs that are found in agriculture, horticulture, forestry, the storage of products of vegetable origin (such as fruit, grain, and timber); and those pests associated with the damage of man-made structures. The term pest encompasses all stages in the life cycle of the pest.

[0026] As used herein, the term "effective amount" refers to the amount of the compound, or a salt thereof, which, upon single or multiple applications provides the desired effect.

[0027] An effective amount is readily determined by the skilled person in the art, using known techniques and by observing results obtained under analogous circumstances. In determining the effective amount, a number of factors are considered including, but not limited to the type of plant or derived product to be applied; the pest to be controlled and its lifecycle; the particular compound applied; the type of application; and other relevant circumstances.

[0028] As used herein, the term “room temperature” or “RT” or “rt” or “ambient temperature” refer to a temperature of about 15° C to about 35° C. For example, rt can refer to a temperature of about 20° C to about 30° C.

[0029] A skilled person is aware that according to the methods of the invention, the compound or compounds are generally applied as part of a pesticidal composition.

[0030] Agrochemical compositions comprising [(1S,2S)-1-methyl-2-(o-tolyl)propyl]-(2S)-2-[(4-methoxy-3- propanoyloxy-pyridine-2-carbonyl)amino]-propanoate and methods for preparation have been disclosed in WO2019 / 173665.

[0031] In one embodiment of the invention there is provided a composition comprising [(1S,2S)-1-methyl-2-(o- tolyl)propyl] (2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino] propanoate according to formula (I), for controlling or preventing infestation of crops by the phytopathogenic microorganism selected from Diaporthe species.

[0032] Diaporthe species are phytopathogenic diseases as described in the present invention and can more preferably comprise at least one of the species selected from Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, Diaporthe longicolla, Diaporthe masirevicii, and Diaporthe pyracanthae. The preferred species is Diaporthe miriciae.

[0033] In the present invention, Diaporthe species, also known as Phomopsis species, are phytopathogen ic fungi which can more preferably comprise at least one of the species selected from Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, Diaporthe longicolla, Diaporthe masirevicii, and Diaporthe pyracanthae. Diaporthe miriciae is also known as Diaporthe ueckeri or Diaporthe ueckerae. The preferred species is Diaporthe miriciae.

[0034] In a preferred embodiment, the Diaporthe species can comprise at least two of the species selected from Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, Diaporthe longicolla, Diaporthe masirevicii, and Diaporthe pyracanthae. The two preferred species are Diaporthe miriciae and Diaporthe sojae. In a further preferred embodiment, the Diaporthe species can comprise at least three of the species selected from Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, Diaporthe longicolla, Diaporthe masirevicii, and Diaporthe pyracanthae. The three preferred species are Diaporthe miriciae, Diaporthe sojae and Diaporthe macadamiae.

[0035] In a preferred embodiment, the Diaporthe species can comprise at least four of the species selected from Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, Diaporthe longicolla, Diaporthe masirevicii, and Diaporthe pyracanthae. The four preferred species are Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae and Diaporthe longicolla.

[0036] In a preferred embodiment, the Diaporthe species can comprise at least five of the species selected from Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, Diaporthe longicolla, Diaporthe masirevicii, and Diaporthe pyracanthae. The five preferred species are Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, Diaporthe longicolla, and Diaporthe masirevicii.

[0037] In an even more preferred embodiment, the Diaporthe species can comprise Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, Diaporthe longicolla, Diaporthe masirevicii, and Diaporthe pyracanthae.

[0038] In another particular embodiment, the Diaporthe species can comprise at least one of the species selected from Diaporthe miriciae, Diaporthe sojae, and Diaporthe macadamiae. More preferably, the Diaporthe species can comprise at least two of the species selected from Diaporthe miriciae, Diaporthe sojae, and Diaporthe macadamiae. Even more preferably, the Diaporthe species can comprise Diaporthe miriciae, Diaporthe sojae, and Diaporthe macadamiae.

[0039] In one embodiment of the invention the Diaporthe species can comprise Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, Diaporthe longicolla, Diaporthe masirevicii, or Diaporthe pyracanthae, or combinations thereof.

[0040] In a preferred embodiment of the invention the Diaporthe species can comprise Diaporthe miriciae, Diaporthe sojae, or Diaporthe macadamiae, or combinations thereof.

[0041] The compound of formula (I) according to the invention is suitable for use on any soybean 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. In a further preferred embodiment, transgenic crops and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof, are treated. Particularly preferably, crops of the plant cultivars which are in each case commercially available or in use are treated according to the invention. Plant cultivars are understood as meaning crops having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, bio- or genotypes.

[0042] The preferred transgenic crops or plant cultivars (obtained by genetic engineering) which are to be treated according to the invention include all plants which, by virtue of the genetic modification, received genetic material which imparts particularly advantageous, useful traits to these plants. Examples of such traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and / or a higher nutritional value of the harvested products, better storage stability and / or processability of the harvested products.

[0043] Further and particularly emphasized examples of such traits are a better defense of the crops against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and also increased tolerance of the crops to certain herbicidally active compounds.

[0044] Traits that are emphasized in particular are the increased defense of the crops against insects, arachnids, nematodes and slugs and snails by virtue of toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CrylA(a), CrylA(b), CrylA(c), CryllA, CrylllA, CrylllB2, Cry9c, Cry2Ab, Cry3Bb and CrylF and also combinations thereof) (referred to herein as "Bt crops"). Traits that are also particularly emphasized are the increased defense of the plants against fungi, bacteria, and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.

[0045] Traits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the "PAT" gene). The genes which impart the desired traits in question can also be present in combination with one another in the transgenic crops.

[0046] In another embodiment of the invention there is provided a composition comprising the compound of formula (I) for controlling or preventing infestation of soybean, or genetically modified soybean, like Bt soybean, by the phytopathogenic microorganism selected from Diaporthe species, comprising the steps of providing a composition comprising said compound of formula (I); and applying said composition to the phytopathogen, to the locus of the phytopathogen, or to a soybean plant susceptible to attack by the phytopathogen.

[0047] In another embodiment of the invention there is provided a composition comprising the compound of formula (I) for controlling or preventing infestation of genetically modified soybean, or genetically modified soybean, like Bt soybean, by the phytopathogenic microorganism selected from Diaporthe species comprising the steps of providing a composition comprising said compound of formula (I); and applying said composition to the phytopathogen, to the locus of the phytopathogen, orto a soybean plant susceptible to attack by the phytopathogen. As used herein, “component (A)” refers to [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy-3- propanoyloxy-pyridine-2-carbonyl)amino] propanoate according to formula (I).

[0048] In one embodiment to the present invention, there is provided a fungicidal composition comprising a mixture of component (A) and a component (B) as active ingredients, wherein component (A) is the compound of formula (I), and component (B) is a compound selected from the group consisting of benzovindiflupyr, bifemetstrobin, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole, metconazole, tetraconazole, fluoxytioconazole, flufenoxadiazam, 2-[2-chloro-4-(4- chlorophenoxy)phenyl]-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propanoate, methyl 3-[(4-chlorophenyl)methyl]-2- hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate, flutriafol, mefentrifluconazole, ipconazole, paclobutrazol, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metalaxyl-M, fenpropidin, fenpropimorph, cyprodinil, spiroxamine, mancozeb, chlorothalonil, folpet, copper-oxychloride, copper-hydroxide, sulphur, oxathiapiprolin, ipflufenoquin, quinofumelin, mandipropamid, fluazinam, fludioxonil, fosetyl-aluminium, acibenzolar-S-methyl, enestrobin, inpyrfluxam, fluindapyr, isoflucypram, metyltetraprole, florylpicoxamid, feneptamidoquin, metcyclofenstrobin, isofetamid, procymidone, carbendazim, fenhexamid, prochloraz, prohexadione-calcium, melaluca alternifolia oil (an extract of the tea tree plant Melaluca alternifolia, which is available as Timorex Gold®, which is a broad-spectrum botanical biofungicide), N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]- cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]- propanamide, 3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl- phenyl)methyl]-5,6-dihydro-4H-1 ,2,4-oxadiazine, cyclobutrifluram, calcium phosphonate, cis-jasmone, trinexapac-ethyl, glyphosate, 2,4-D (2,4-dichlorophenoxyacetic acid) and thiamethoxam, for controlling or preventing infestation of crops by the phytopathogenic microorganism selected from Diaporthe species. Preferably said crops are selected from soybean. In one embodiment said crops are genetically modified crops, preferably Bt crops, more preferably Bt soybean plants.

[0049] In general, the weight ratio of component (A) to component (B) may be from 1000: 1 to 1 :1000, may be from 100:1 to 1 :100, preferably from 50:1 to 1 :50, more preferably from 20:1 to 1 :40, even more preferably from 15:1 to 1:30, still more preferably from 12:1 to 1 :25, or from 10:1 to 1 :20, or from 10:1 to 1 :10, or from 5:1 and 1 :15, or from 5: 1 to 1 :5, or from 4:1 to 1:4, or from 3:1 to 1 :10, or from 3:1 to 1 :3, or from 2:1 to 1 :5, or 1 :1.

[0050] In any of the compositions according to the invention, the composition may comprise an additional active ingredient component (C), which is different to component (B), and is selected from the group consisting of metyltetraprole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metominostrobin, prothioconazole, cyproconazole, difenoconazole, tebuconazole, propiconazole, epoxiconazole, hexaconazole, mefentrifluconazole, metconazole, benzovindiflupyr, bifemetstrobin, pydiflumetofen, fluxapyroxad, sedaxane, bixafen, isopyrazam, fluopyram, fluindapyr, isoflucypram, inpyrfluxam, quinofumelin, ipflufenoquin, aminopyrifen, fluazinam, fludioxonil, fenpicoxamid, florylpicoxamid, flufenoxadiazam, fenpropidin, fenpropimorph, feneptamidoquin, metcyclofenstrobin, mancozeb, chlorothalonil, cyclobutrifluram, copper-oxychloride, copper-hydroxide, N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5- (trifluoromethy l)-1 ,2,4-oxadiazol-3-y l]pheny l]methy l]propanamide, and 3-[3-(3-chloro-2-fluoro-phenoxy)-6- methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1 ,2,4-oxadiazine, for controlling or preventing infestation of crops by the phytopathogenic microorganism selected from Diaporthe species. Preferably said crops are selected from soybean. In one embodiment said crops are genetically modified crops, preferably Bt crops, more preferably Bt soybean plants.

[0051] The component (C) compounds are referred to herein and above by a so-called "ISO common name" or another "common name" being used in individual cases or a trademark name. The component (C) compounds are known and are commercially available and / or can be prepared using procedures known in the art.

[0052] In another embodiment of the present invention, there is provided a fungicidal composition comprising a mixture of component (A) and a component (B) and a component (C) as active ingredients, wherein component (A) is the compound of formula (I), and component (B) and (C) are a compound selected from the group consisting of benzovindiflupyr, bifemetstrobin, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole, metconazole, tetraconazole, fluoxytioconazole, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentane- carboxylate, flutriafol, mefentrifluconazole, ipconazole, paclobutrazol, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metalaxyl-M, fenpropidin, fenpropimorph, cyprodinil, spiroxamine, mancozeb, chlorothalonil, folpet, copper-oxychloride, copper-hydroxide, sulphur, oxathiapiprolin, ipflufenoquin, quinofumelin, mandipropamid, fluazinam, fludioxonil, fosetyl-aluminium, acibenzolar- S-methyl, enestrobin, inpyrfluxam, fluindapyr, isoflucypram, metyltetraprole, florylpicoxamid, flufenoxadiazam, feneptamidoquin, metcyclofenstrobin, isofetamid, procymidone, carbendazim, fenhexamid, prochloraz, prohexadione-calcium, melaluca alternifolia oil (an extract of the tea tree plant Melaluca alternifolia, which is available as Timorex Gold®, which is a broad-spectrum botanical biofungicide), 3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl- phenyl)methyl]-5,6-dihydro-4H-1 ,2,4-oxadiazine, N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]propenamide, cyclobutrifluram, calcium phosphonate, cis-jasmone, trinexapac-ethyl, glyphosate, 2,4-D (2,4-dichlorophenoxyacetic acid) and thiamethoxam, wherein component (B) and (C) are not the same compound, for controlling or preventing infestation of crops by the phytopathogenic microorganism selected from Diaporthe species. Preferably said crops are selected from soybean. In one embodiment said crops are genetically modified crops, preferably Bt crops, more preferably Bt soybean plants.

[0053] Components (B) and (C) in combination with component (A) may enhance the effectiveness of the latter against fungi, and vice versa. Additionally, the fungicidal compositions may be effective against a wider spectrum of fungal pathogens that can be combated with the individual active ingredients when used solely. Generally, the weight ratio of component (A) to the mixture of components (B) and (C) may be from 100:1 to 1:100, 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.

[0054] In embodiments of the invention where the composition comprise a component (A), a component (B) and a component (C), the weight ratio of component (A) to the sum of component (B) and component (C) may be from 100:1 to 1 :100, preferably from 50:1 to 1 :50, more preferably from 20:1 to 1 :40, even more preferably from 15:1 to 1 :30, still more preferably from 12:1 to 1 :25, or from 10: 1 to 1 :20, or from 10:1 to 1 :10, or from 5:1 and 1:15, or from 5:1 to 1:5, or from 4:1 to 1 :4, or from 3:1 to 1 :10, or from 3:1 to 1 :3, or from 2:1 to 1:5, or 1 :1.

[0055] The component (B) compounds are referred to herein and above by a so-called "ISO common name" or another "common name" being used in individual cases or a trademark name. The component (B) compounds are known and are commercially available and / or can be prepared using procedures known in the art and / or procedures reported in the literature such as, for instance, WO 2015 / 155075 and WO 2016 / 202742, WO 2017 / 005710, WO 2018 / 108977, WO 2018 / 153707, WO 2018 / 098216, WO

[0056] 2019 / 093522, WO 2018 / 145921 , WO 2015 / 185485, WO 2017 / 076742, WO 2017 / 081311, WO

[0057] 2017 / 085100, WO 2017 / 093019, WO 2017 / 178245, and WO 2017 / 211649.

[0058] Compound (5R)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl). methyl]-5,6-dihydro-4H-1 ,2,4-oxadiazine has been disclosed and may be prepared from the methods described in W02020 / 127780, W02021 / 255070, WO2025 / 056725, WO2025 / 056724, and

[0059] W02025 / 093606. If not otherwise mentioned the compound can be used in racemic form or as the R- or S-enantiomer or as a mixture of the R / S enantiomers.

[0060] In embodiments of the invention where the composition comprise a component A, wherein said component A is the compound of formula (I), a first component (B) and a second component (B), wherein said second component (B) is different than said first component (B), the weight ratio of component (A) to the sum of first component (B) and second component (B) may be from 100:1 to 1 :100, preferably from 50:1 to 1:50, more preferably from 20:1 to 1 :40, even more preferably from 15:1 to 1:30, still more preferably from 12:1 to 1 :25, or from 10:1 to 1 :20, or from 10:1 to 1 :10, or from 5:1 and 1 :15, or from 5:1 to 1 :5, or from 4:1 to 1:4, or from 3:1 to 1 :10, or from 3:1 to 1:3, or from 2:1 to 1:5, or 1 :1.

[0061] Throughout this document the expression “composition” stands for the various mixtures or combinations of component A, wherein said component A is the compound of formula (I), and components (B) (including the above-defined embodiments), 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 when 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 component A, wherein said component A is the compound of formula (I), and component (B) is not essential for working the present invention. In one embodiment of the present invention, there is provided a method for controlling harmful fungi, wherein the pest, their habitat, breeding grounds, their locus or the plants to be protected against pest attack, the soil or plant propagation material (preferably seed) are treated with a pesticidally effective amount of the compound of formula (I) according to the present invention.

[0062] In one embodiment of the present invention, there is provided a method for controlling harmful fungi, wherein the pest, their habitat, breeding grounds, their locus or the plants to be protected against pest attack, the soil or plant propagation material (preferably seed) are treated with a composition comprising a pesticidally effective amount of the compound of formula (I) according to the present invention.

[0063] Preferably the compound of the present invention and compositions comprising said compound of formula (I) are suitable for controlling fungal plant diseases.

[0064] The compound of the present invention are also important for controlling a multitude of fungi on various cultivated plants, such as bananas, cotton, vegetable species, for example cucumbers, beans, and cucurbits; cereals such as maize, wheat, rye, barley, rice, oats; grass coffee, potatoes, sweet potatoes, corn, fruit species, soybean, tobacco, tomatoes, grapevines, ornamental plants, sugar cane and also on a large number of seeds. In a preferred embodiment, the compound of formula (I), according to the present invention, is used in soybean, cotton, and corn, preferably soybean. In a preferred embodiment the compound of formula (I), according to the present invention, is used on genetically modified plants (crops) selected from soybean, cotton, and corn. Preferably said genetically modified crops selected from soybeans, cotton, and corn are Bt crops, like Bt soybeans, Bt cotton and Bt corn. In a more preferred embodiment, the compound of formula (I), according to the present invention, is used on genetically modified crops selected from soybean. Preferably said genetically modified crops selected from soybeans are Bt crops, like Bt soybeans.

[0065] In one embodiment, the compound of formula (I), according to the present invention, is suitable for controlling the following fungal diseases on soybeans: Alternaria spp. (Alternaria leaf spot); Ascochyta spp. (Leaf spots); Cercospora spp. (leaf spots), e.g. C. sojina or C. kikuchir, Colletotrichum spp. (teleomorph: Glomerella) (anthracnose), e.g. C. truncatum, C. cliviicola or C. gloeosporioides', Corynespora cassiicola (leaf spots); Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot); Diaporthe spp., e.g. Diaporthe miriciae (also known as Diaporthe ueckeri or Diaporthe ueckerae), Diaporthe macadamiae and Diaporthe longicolla (damping off, seeds decay, anomaly); Erysiphe diffusa (Powdery mildew); Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot), e.g. F. tucumaniae and F. brasiliense (each causing sudden death syndrome on soybeans); Macrophomina phaseolina (syn. phaseoli) (root and stem rot); Peronospora spp. (downy mildew), e.g. P. manshurica; Phakopsora pachyrhizi and P. meibomiae (soybean rust); Phialophora spp., e.g. P. gregata (brown stem rot); Phomopsis spp., e.g. P. phaseoli (teleomorph: Diaporthe phaseolorum)', Pythium spp. (damping-off); Phytophthora spp. (wilt, root, leaf, fruit and stem root), e.g. P. megasperma (syn. P. sojae)', Rhizoctonia solani (root and stem rot); Sclerotinia spp. (stem rot or white mold); Septoria glycines (brown spot); S. rolfsii (syn. Athelia rolfsii)', Thielaviopsis spp. (black root rot).

[0066] Preferably, the compound of formula (I), according to the present invention, is suitable for controlling the soybean diseases caused by phytopathogenic fungi selected from Diaporthe species. Preferably, the compound of the invention or fungicidal compositions according to the present invention comprising said compound may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi selected from Diaporthe species on soybean.

[0067] In another embodiment of the present invention, the compound of formula (I), is suitable for controlling or preventing an infestation of plants, e.g., useful plants such as crop plants, propagation material thereof, e.g., seeds, harvested crops, e.g., harvested food crops, or of non-living materials by Diaporthe spp., which comprises the application of the compound of formula (I) according to the invention as defined herein 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.

[0068] 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.

[0069] 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 the compound of formula (I) according to the invention, or an agrochemical composition which contains at least one compound of formula (I), 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 compound of formula (I) according to the invention 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 compound of formula (I) 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 compound of formula (I) may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.

[0070] A formulation, e.g., a composition containing the compound of formula (I), according to the invention and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound of formula (I), may be prepared in a known manner, typically by intimately mixing and / or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface active compounds (surfactants).

[0071] Advantageous rates of application are normally from 5g to 2kg of active ingredient (a.i.) per hectare (ha), preferably from 10g to 1 kg a.i. / ha, most preferably from 20g to 600g a.i. / ha. When used as seed drenching agent, convenient dosages are from 10mg to 1g of active substance per kg of seeds.

[0072] The term “g a.i. / ha” as used herein refer to the application rate given in gram [g] of active ingredient [a.i.] per unit of surface [ha]. The unit hectare (symbol ha) is the metric unit of area that equals a square with 100 m side (1 hm2) or 10,000 square meters. Hectare is a commonly used unit of area in the metric system.

[0073] When the combinations of the present invention are used for treating seed, rates of 0.001 to 50 g of the compound of formula (I) per kg of seed, preferably from 0.01 to 10g per kg of seed are generally sufficient.

[0074] Suitably, a composition comprising the compound of formula (I), according to the present invention is applied either preventative, meaning prior to disease development or curative, meaning after disease development. The compositions of the invention may be employed in any conventional form, for example in the form of a twin pack, a powder for dry seed treatment (DS), an emulsion for seed treatment (ES), a flowable concentrate for seed treatment (FS), a solution for seed treatment (LS), a water dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EC), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (CD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0075] Such compositions may be produced in conventional manner, e.g., by mixing the active ingredients with appropriate formulation inerts (diluents, solvents, fillers, and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners, and compounds that provide adjuvancy effects). Also, conventional slow-release formulations may be employed where long lasting efficacy is intended. Particularly formulations to be applied in spraying forms, such as water dispersible concentrates (e.g., EC, SC, DC, CD, SE, EW, EC and the like), wettable powders and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvancy effects, e.g., the condensation product of formaldehyde with naphthalene sulfonate, an alkyl aryl sulfonate, a lignin sulfonate, a fatty alkyl sulphate, and ethoxylated alkylphenol and an ethoxylated fatty alcohol.

[0076] A seed dressing formulation is applied in a manner known per se to the seeds employing the combination of the invention and a diluent in suitable seed dressing formulation form, e.g., as an aqueous suspension or in a dry powder form having good adherence to the seeds. Such seed dressing formulations are known in the art. Seed dressing formulations may contain the single active ingredients or the combination of active ingredients in encapsulated form, e.g., as slow-release capsules or microcapsules.

[0077] In another embodiment of the invention, there is provided a method of controlling or preventing infestation of genetically modified crops by especially phytopathogenic fungi, selected from Diaporthe species, wherein the compound of formula (I), according to the present invention is applied to said crops. Preferably said genetically modified crops are selected from soybean, cotton and maize. In another preferred embodiment said genetically modified crops are Bt crops, selected from Bt soybean, Bt cotton and Bt maize. In another preferred embodiment, genetically modified crops are Bt crops, selected from Bt soybean, and Bt cotton. More preferably said genetically modified crops are selected from soybean, even more preferably Bt soybean crop.

[0078] Examples of commercially available genetically modified soybean, which can preferably be treated according to the invention, include, but are not limited to, commercially available products such Liberty Link™ Soybean, Cultivance, Conkesta Enlist E3™ Soybean, Treus™, Plenish™, Liberty Link® GT27™, Roundup Ready™ Soybean, Roundup Ready™ Liberty Link® soybean, Verdeca HB4 Soybean, Intacta™ Roundup Ready™ 2 Pro, Genuity® Roundup Ready™ 2 Xtend™, Intacta®, lntacta®2, Intacta® Roundup Ready™ 2 Pro (lntacta®RR2 PRO), lntacta®2 Xtend™, Conkesta Soybean, Enlist™ Soybean, Enlist E3™ Soybean, Roundup Ready™ 2 Xtend™, Genuity® Roundup Ready 2 Yield™, Herbicide-tolerant Soybean line, Optimum GAT™, Vistive Gold™. Preferably, the genetically modified soybean, which can be treated according to the invention, include, but are not limited to, commercially available products such as Liberty Link™ Soybean, Cultivance, Conkesta Enlist E3™ Soybean, Treus™, Plenish™, Liberty Link® GT27™, Roundup Ready™ Soybean, Roundup Ready™ Liberty Link® soybean, Verdeca HB4 Soybean, Intacta™ Roundup Ready™ 2 Pro, Genuity® Roundup Ready™ 2 Xtend™.

[0079] In one embodiment of the invention, there is provided a method of controlling or preventing infestation of genetically modified soybean by especially phytopathogenic fungi, selected from Diaporthe species, wherein the compound of formula (I) according to the present invention is applied to said soybean, and wherein said soybean are Bt soybeans. Preferably said Bt soybeans are selected from Intacta RR2 PRO®, or Conkesta Enlist E3®.

[0080] In a preferred embodiment of the invention, there is provided a method for controlling phytopathogenic fungi, selected from Diaporthe species, on soybean, wherein said soybean are genetically modified soybean, preferably Bt soybean, characterized by comprising the step of contacting the plant, parts thereof, propagation material thereof, the pests, their food source, habitat, or breeding ground with [(1S,2S)-1- methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino] propanoate (compound formula (I) according to the present invention).

[0081] In a more preferred embodiment of the invention, there is provided a method for controlling phytopathogenic fungi, selected from Diaporthe species, on soybean, wherein said soybean are genetically modified soybean, preferably Bt soybean, characterized by comprising the step of contacting the plant, parts thereof, propagation material thereof, the pests, their food source, habitat, or breeding ground with [(1S,2S)-1- methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino] propanoate (compound of formula (I) according to the present invention), wherein said Diaporthe species is selected from Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, or combinations thereof.

[0082] [(1 S,2S)-1 -methy l-2-(o-toly IJpropy I] (2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino] propanoate according to formula (I), or fungicidal compositions comprising said compound according to the present invention, may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi, selected from Diaporthe species, on soybean, wherein said Diaporthe species is selected from Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, or combinations thereof.

[0083] In one embodiment, the compound of formula (I), according to the present invention, or fungicidal compositions comprising said compound according to the present invention, may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi, selected from Diaporthe species, on genetically modified soybean, preferably Bt soybean, wherein said Diaporthe species is selected from Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, or combinations thereof.

[0084] Under certain circumstances, fungicidal compositions according to the present invention comprising the compound of formula (I), when used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi, selected from Diaporthe species, on crops selected from soybean (in particular any of the transgenic crops as described above), may display a synergistic interaction between the active ingredients. In particular, transgenic soybean expressing toxins, for example insecticidal proteins such as deltaendotoxins, e.g., Cry1 Ac (Cry1 Ac Bt protein). Accordingly, this may include transgenic soybean comprising event MON87701 (disclosed in W02009 / 064652), event MON87701 x MON89788 (disclosed in WO2014 / 170327, e.g. commercially available as Intacta RR2 PRO® soybean), event MON87751 (disclosed in WO2014 / 201235), event DAS-44406-6 (e.g., commercially available as Enlist E3™, DAS- 44406-6, disclosed in WO2012 / 075426), or event DAS-81419-2 (described in WO2013 / 016527, e.g., commercially available as Conkesta™ soybean); event DAS-81419-2 x DAS-44406-6 (e.g., commercially available as Conkesta™ Enlist E3™ Soybean).

[0085] Useful transgenic events in transgenic soybean, which can be treated according to the invention, include event DAS-44406-6 / pDAB8264.44.06.1 (soybean, herbicide-tolerance, disclosed in WO2012 / 075426); event DAS-81419-2 (described in WO2013 / 016527 (e.g., commercially available as aka Conkesta™ soybean, Conkesta™ Enlist E3™ soybean, DAS-81419-2 x DAS-44406-6); event DAS-14536- 7 / pDAB8291.45.36.2 (soybean, herbicide-tolerance, disclosed in WO2012 / 075429); DAS-68416-4 (soybean, herbicide-tolerance, ATCC Accession No. PTA-10442, disclosed in WO2011 / 066384, WO2011 / 066360); event DP-305423-1 (soybean, quality mark, disclosed in W02008 / 054747, e.g. commercially available as Treus™, Plenish™, Plenish® High Oleic Soybeans); event DP-356043-5 (soybean, herbicide-tolerance, deposited as ATCC PTA-8287, disclosed in W02008 / 002872, e.g. commercially available as Optimum GAT™); event FG72 (soybean, herbicide-tolerance, disclosed in WO2011 / 063413); event LL27 (soybean, herbicide-tolerance, disclosed in W02006 / 108674); event LL55 (soybean, herbicide-tolerance, disclosed in WO 2006 / 108675); event EE-GM3 / FG72 (soybean, herbicidetolerance) optionally stacked with event EE-GM1 / LL27 or event EE-GM2 / LL55 (disclosed in WO2011 / 063413); event MON87701 (soybean, insect control, disclosed in W02009 / 064652, WO2014 / 170327); event MON87701 x MON89788 (disclosed in WO2014 / 170327, e.g. commercially available as Intacta RR2 PRO® soybean); event MON87705 (soybean, improved fatty acid profile, herbicide-tolerance, disclosed in W02010 / 037016 or US20100080887A, e.g. commercially available as Vistive Gold™); event MON87751 (lepidopteran-resistant, ATCC accession no. PTA-120166. disclosed in WO2014 / 201235); event MON87751xMON87701xMON89788xMON87708 (commercially available as Intacta2 Xtend®); event MON87708 (soybean, herbicide-tolerance, disclosed in WO2011 / 034704, e.g. commercially available as Genuity® Roundup Ready™ 2 Xtend™); event MON87708xMON89788 (soybean, e.g. commercially available as Roundup Ready™ 2 Xtend™); event MON87712 (soybean, yield, disclosed in WO2012 / 051199); event MON87754 (soybean, quality feature, disclosed in WO2010 / 024976); event MON87769 (soybean, quality attribute, disclosed in W02009 / 102873); event MON89788 (soybean, herbicide-tolerance, disclosed in W02006 / 130436, e.g. commercially available as Genuity® Roundup Ready 2 Yield™); event SYHT0H2 / SYN-000H2-5 (soybean, herbicide-tolerance, disclosed in WO2012 / 082548); event DAS-21606-3 (soybean, herbicide-tolerance, disclosed in WO2012 / 033794); event 8264.44.06.1 (soybean, stacked herbicide-tolerance, disclosed in W02022 / 012075426); event pDAB8291.45.36.2 (soybean, stacked herbicide-tolerance, disclosed in WO2012 / 075429); event pDAB8264.42.32.1 (soybean, stacked herbicide-tolerance, disclosed in WO2013 / 010094); event A2704- 12 (glufosinate tolerance, disclosed in W02006 / 108647); event A5547-127 (phosphinothricin tolerant, disclosed in W02006 / 108675); event BPS-CV127- 91 (herbicide tolerance, disclosed in WO 2010 / 080829); event GU262 (phosphinothricin tolerant, described in APHIS regulatory reference US 98-238-01 p); event MON 87708 x MON 89788 x A5547-127; G72xA5547-127 (event code: MST-FG072-3xACS-GM006-4, e.g. commercially available as Liberty Link™ soybean), event MON-04032-6 (event code: GTS 40-3-2, http: / / www.agbios.com / static / cropdb / LONG-GTS-40-3-2-printer.html, e.g. commercially available as Roundup Ready® soybean), event HB4 (event code IND-00410-5, US2022 / 009011 , e.g., commercially available as Verdeca HB4 Soybean), even MON87701 x MON89788 (event code: MON-87701-2 x MON- 89788-1 , commercially available as Intacta™ Roundup Ready™ 2 Pro), event name GTS 40-3-2 x A5547- 127 (event code: MON-04032-6 x ACS-GM006-4, commercially available as Roundup Ready™ Liberty Link® soybean), event name GTS 40-3-2 (40-3-2) (event code: MON-04032-6, commercially available as Roundup Ready™ soybean), event name: FG72 x A5547-127 (event code: MST-FG072-2 x ACS- GM006-4, commercially available as Liberty Link® GT27™).

[0086] Particularly useful transgenic events in transgenic soybean, which can preferably be treated according to the invention, include event A2704-12 (glufosinate tolerance, disclosed in W02006 / 108647, e.g., commercially available as Liberty Link™ soybean), event A5547-127 (phosphinothricin tolerant, disclosed in W02006 / 108675, US8952142B2, e.g., commercially available as Liberty Link™ soybean); A5547-35 (event code: ACS-GM008-6, gene: pat, e.g. commercially available as Liberty Link™ soybean), event MON89788 (soybean, herbicide-tolerance, disclosed in W02006 / 130436, e.g. commercially available as Genuity® Roundup Ready 2 Yield™); DP-305423-1 (soybean, quality mark, disclosed in W02008 / 054747, e.g., commercially available as Treus™, Plenish™, Plenish® High Oleic Soybeans); event MON87701 (soybean, insect resistant, disclosed in W02009 / 064652); event MON87701 x MON89788 (disclosed in WO2014 / 170327, e.g. commercially available as Intacta RR2 PRO® soybean); event MON87705 (soybean, improved fatty acid profile, herbicide-tolerance, disclosed in W02010 / 037016 or US20100080887A, e.g. commercially available as Vistive Gold™); event FG72 (soybean, herbicide-tolerance, disclosed in WO2011 / 063413); evet FG72xA5547-127 (e.g. commercially available as LibertyLink® GT27™); event SYHT0H2 / SYN-000H2-5 (soybean, herbicide-tolerance, disclosed in WO2012 / 082548); event DAS- 81419-2 (described in WO2013 / 016527, e.g., commercially available as Conkesta™ soybean); event DAS- 44406-6 (disclosed in WO2012 / 075426, e.g., commercially available as Enlist E3™), or event DAS-81419- 2 (described in WO2013 / 016527, e.g., commercially available as Conkesta™ soybean); DAS81419- 2xDAS4406 (e.g., commercially available as Conkesta™ Enlist E3™ soybean); event DP305423x GTS 40- 3-2 (soybean, quality mark, disclosed in W02008 / 054747, e.g. commercially available as Plenish® High Oleic Soybeans); event DP-356043-5 (soybean, herbicide-tolerance, deposited as ATCC PTA-8287, disclosed in W02008 / 002872, e.g. commercially available as Optimum GAT™), event MON-04032-6 (event code: GTS 40-3-2, http: / / www.agbios.com / static / cropdb / LONG-GTS-40-3-2-printer.html, e.g. commercially available as Roundup Ready® soybean).

[0087] Furthermore, such a list of transgenic events is provided by the United States Department of Agriculture's (USDA) Animal and Plant Health Inspection Service (APHIS) and can be found on their website on the World Wide Web at aphis.usda.gov.

[0088] Transgenic soybean events comprising herbicide tolerance genes are for example, but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127. According to one embodiment of the invention, there is provided the use of the compound of formula (I) for controlling phytopathogenic fungi in genetically modified soybean, wherein said transgenic soybean events comprising herbicide tolerance genes are for example, but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.

[0089] According to one embodiment of the invention, there is provided the use of the compound of formula (I) for controlling phytopathogenic fungi in genetically modified soybean, wherein said transgenic soybean events comprising herbicide tolerance genes are for example, but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.

[0090] In another embodiment, the compound of formula (I), according to the present invention, or fungicidal compositions comprising said compound according to the present invention, may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi, selected from Diaporthe species, on genetically modified cotton.

[0091] Transgenic cotton events comprising herbicide tolerance genes are for example, but not excluding others, 19-51 a, 31707, 42317, 81910, 281 -24-236, 3006-210-23, BXN1021 1, BXN 10215, BXN10222, BXN 10224, MON1445, MON1698, MON88701 , MON88913, GHB1 19, GHB614, LLCotton25, T303-3 and T304-40.

[0092] Transgenic cotton events comprising genes for insecticidal proteins are for example, but not excluding others, SGK321, MON531 , MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA- 601 , Eventl, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281 -24-236, 3006-210- 23, GHB1 19 and SGK321. Increased yield has been created by increasing ear biomass using the transgene athb17, being present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.

[0093] T ransgenic cotton events comprising glufosinate tolerance genes are for example, but not excluding others, 3006-210-23 x 281-24-236 x MON 1445 (event code: DAS-21023-5 x DAS- 24236-5 x MON-01445-2, gene: bar, e.g., commercially available as WideStrike™ Roundup Ready™ Cotton), 3006-210-23 x 281- 24-236 x MON88913 (event code: DAS-21023-5 x DAS-24236-5 x MON-88913-8, gene: bar, e.g., commercially available as Widestrike™ Roundup Ready Flex™ Cotton), 3006-210-23 x 281-24-236 x MON88913 x COT102 (event code: DAS- 21023-5 x DAS-24236-5 x MON-88913-8 x SYN-IR102-7, gene: pat, e.g., commercially available as Widestrike™ x Roundup Ready Flex™ x VIPCOT™ Cotton), GHB614 x LLCotton25 (event code: BCS-GH002-5 x ACS-GH001-3, gene: bar, e.g., commercially available as GlyTol™ Liberty Link™), GHB614 x T304-40 x GHB119 (event code: BCS-GH002-5 x BCS-GH004-7 x BCS-GH005-8, gene: bar, e.g., commercially available as Glytol™ x Twinlink™), LLCotton25 (event code: ACS-GH001-3, gene: bar, e.g., commercially available as ACS- GH001-3), GHB614 x T304-40 x GHB119 x COT102 (event code: BCS-GH002-5 x BCS-GH004-7 x BCS-GH005-8 x SYN-IR102-7, gene: bar, e.g., commercially available as Glytol™ x Twinlink™ x VIPCOT™ Cotton), LLCotton25 x MON 15985 (event code: ACS-GH001-3 x MON-15985-7, gene: bar, e.g., commercially available as Fibermax™ Liberty Link™ Bollgard II™), T304-40 x GHB1 19 (event code: BCS-GH004-7 x BCS-GH005-8, gene: bar, e.g., commercially available as TwinLink™ Cotton), GHB614 x T304-40 x GHB1 19 x COT102 (event code: BCS-GH002-5 x BCS-GH004-7 x BCS-GH005-8 x SYN-IR102-7, gene: bar, e.g., commercially available as Glytol™ x Twinlink™ x VIPCOT™ Cotton), GHB1 19 (event code: BCS-GH005-8, gene: bar), GHB614 x LLCotton25 x MON15985 (event code: CS-GH002-5 x ACS-GH001-3 x MON-15985-7, gene: bar), MON 88701-3 (event code: MON88701, gene: bar), T303-3 (event code: BCS-GH003-6, gene: bar), T304-40 (event code: BCS-GH003-6, gene: bar), (event code: BCS-GH004-7, gene: bar), 81910 (event code: DAS- 81910-7, gene: pat), MON8870 (event code: MON 88701-3, gene: bar), MON88701 x MON88913 (event code: MON 88701-3 x MON-88913-8, gene: bar), MON88701 x MON88913 x MON15985 (event code: MON 88701-3 x MON-88913-8 x MON-15985-7, gene: bar), 281-24-236 x 3006-210-23 x COT102 x 81910 (event code: DAS-24236-5 x DAS-21023-5 x SYN-IR102-7 x DAS-81910-7, gene: pat), COT102 x MON15985 x MON88913 x MON88701 (event code: SYN-IR102-7 x MON-15985-7 x MON-88913-8 x MON 88701-3, gene: bar) and 3006-210-23 x 281-24-236 x MON88913 x COT102 x 81910 (event code: DAS-21023-5 x DAS-24236-5 x MON-88913-8 x SYN-IR102-7 x DAS-81910-7, gene: pat).

[0094] Examples of commercially available genetically modified cotton, which can preferably be treated according to the invention, include, but are not limited to, commercially available products such as WideStrike™ Cotton, Bollgard® III x Roundup Ready™ Flex™, GlyTol™, GlyTol™ Liberty Link™, Glytol™ x Twinlink™, GlyTol LibertyLink TwinLink® Plus, Fibermax™ Liberty Link™, Roundup Ready™ Cotton, Bollgard II™ Cotton, Bollgard™ Cotton, Ingard™, Roundup Ready™ Bollgard™ Cotton, Roundup Ready™ Flex™ Cotton, Roundup Ready™ Flex™ Bollgard II™ Cotton or TwinLink™ Cotton.

[0095] In another embodiment, the compound of formula (I), according to the present invention, or fungicidal compositions comprising said compound according to the present invention, may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi, selected from Diaporthe species, on genetically modified corn (maize).

[0096] Transgenic corn events comprising herbicide tolerance genes include, but are not limited to, DAS40278, MON801 , MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21 , MZHG0JG, HCEM485, VCO-01981-5, 676, 678, 680, 33121 , 4114, 59122, 98140, Bt10, Bt176, CBH-351 , DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.

[0097] T ransgenic corn events comprising genes for insecticidal proteins or double stranded RNA include, but are not limited to, Bt10, Bt11 , Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121 , 4114, 5307, 59122, TC1507, TC6275, CBH-351 , MIR162, DBT418 and MZIR098.

[0098] Particularly useful transgenic events in transgenic corn, maize, which can preferably be treated according to the invention, include event 4114 x DAS40278 (event code DP-004114-3 x DAS-40278-9, commercially available as Enlist TM), event 4114 x MIR604 x NK603 (event code: DP-004114-3 x SYN-IR604-5 x MON- 00603-6, commercially available as Roundup Ready 2™ Agrisure RW™), event 4114 x MON810 (Event Code DP-004114-3 x MON-00810-6, commercially available as YieldGard™), event 4114 x MON810 x MIR604 (Event Code DP-004114-3 x MON-00810-6 x SYN-IR604-4, commercially available as Agrisure RW™ YieldGard™), event 4114 x MON810 x NK603 (event code DP-004114-3 x MON-00810-6 x MON- 00603-6, commercially available as Roundup Ready 2™ YieldGard™), event 4114 x MON87411 x DAS40278 (event code P-004114-3 x MON-87411-9 x DAS-40278-9, commercially available as Enlist™), event 4114 x MON89034 (event code DP-004114-3 x MON-89034-3, commercially available as YieldGard VT Pro™), event 4114 x MON89034 x DAS40278 (event code DP-004114-3 x MON-89034-3 x DAS-40278-9, commercially available as Enlist™ YieldGard VT Pro™), event 4114 x MON89034 x MON87411 (event Code DP-004114-3 x MON-89034-3 x MON-87411-9, commercially available as YieldGard VT Pro™), event 114 x MON89034 x MON87411 x DAS40278 (Event Code DP-004114-3 x MON-89034-3 x MON-87411-9 x DAS-40278-9, commercially available as Enlist™ YieldGard VT Pro™), event 4114 x MON89034 x MON87411 x DAS40278 (Event Code DP-004114-3 x MON-89034-3 x MON- 87411-9 x DAS-40278-9, commercially available as Enlist™ YieldGard VT Pro™), event 4114 x NK603 (Event Code DP-004114-3 x MON-00603-6, commercially available as Roundup Ready 2™), event 5307 (Event Code SYN-05307-1 , commercially available as Agrisure® Duracade™), event 5307 x MIR604 x Bt11 x TC1507 x GA21 (Event Code SYN-05307-1 x SYN-IR604-5 x SYN-BT011-1 x DAS-01507-1 x MON-00021-9, commercially available as Agrisure® Duracade™ 5122), event 5307 x MIR604 x Bt11 x TC1507 x GA21 x MIR162 (Event Code SYN-05307-1 x SYN-IR604-5 x SYN-BT011-1 x DAS-01507-1 x MON-00021-9 x SYN-IR162-4, commercially available as Agrisure® Duracade™ 5222), event 59122 (Event Code DAS-59122-7, commercially available as Herculex™ RW), event 59122 x NK603 (Event Code DAS-59122-7 x MON-00603-6, commercially available as Herculex™ RW Roundup Ready™ 2), event Bt11 (X4334CBR, X4734CBR) (Event Code SYN-BT011-1, commercially available as Agrisure™ CB / LL), event Bt11 x 59122 x MIR604 x TC1507 x GA21 (Event Code SYN-BT011-1 x DAS-59122-7 x SYN- IR604-5 x DAS-01507-1 x MON-00021-9, commercially available as Agrisure® 3122), event Bt11 x GA21 (Event Code SYN-BT011-1 x MON-00021-9, commercially available as Agrisure™ GT / CB / LL), event Bt11 x MIR162 (Event Code SYN-BT011-1 x SYN-IR162-4, commercially available as Agrisure® Viptera™ 2100), event Bt11 x MIR162 x GA21 (Event Code SYN-BT011-1 x SYN-IR162-4 x MON-00021- 9, commercially available as Agrisure® Viptera™ 3110), event BT11 x MIR162 x MIR604 (Event Code SYN-BT011-1 x SYN-IR162-4 x SYN-IR604-5, commercially available as Agrisure® Viptera™ 3100), event Bt11 x MIR162 x MIR604 x GA21 (Event Code SYN-BT011-1 x SYN-IR162-4 x SYN-IR604-5 x MON-00021-9, commercially available as Agrisure® Viptera™ 3111 , Agrisure® Viptera™ 4), event Bt11 x MIR162 x NK603 (Event Code SYN-BT011-1 x SYN-IR162-4 x MON-00603-6, Commercially available as Agrisure® Viptera™ 2100 Roundup Ready™ 2 Maize), event Bt11 x MIR162 x TC1507 x GA21 (Event Code SYN-BT011-1 x SYN-IR162-4 x DAS-01507-1 x MON-00021-9, Commercially available as Agrisure™ Viptera 3220), event Bt11 x MIR604 (Event Code SYN-BT011-1 x SYN-IR604-5, Commercially available as Agrisure™ CB / LL / RW), event Bt11 x MIR604 x GA21 (Event Code SYN-BT011- 1 x SYN-IR604-5 x MON-00021-9, Commercially available as Agrisure™ 3000GT), event Bt176 (176) (Event Code SYN-EV176-9, Commercially available as NaturGard KnockOut™, Maximizer™), event CBH- 351 (Event Code ACS-ZM004-3, Commercially available as Starlink™ Maize), event DBT418 (Event Code DKB-89614-9, Commercially available as Bt Xtra™ Maize), event GA21 x MON810 (Event Code MON-00021-9 x MON-00810-6, Commercially available as Roundup Ready™ YieldGard™ maize), event LY038 x MON810 (Event Code REN-00038-3 x MON-00810-6, Commercially available as Mavera™ YieldGard™ Maize), event MIR162 (Event Code SYN-IR162-4, Commercially available as Agrisure™ Viptera), event MIR604 (Event Code SYN-IR604-5, Commercially available as Agrisure™ RW), event MIR604 x GA21 (Event Code SYN-IR604-5 x MON-00021-9, Commercially available as Agrisure™ GT / RW), event MON810 (Event Code MON-00810-6, Commercially available as YieldGard™, MaizeGard™), event MON810 x MON88017 (Event Code MON-00810-6 x MON-88017- 3, Commercially available as YieldGard™ VT Triple), event MON863 (Event Code MON-00863-5, Commercially available as YieldGard™ Rootworm RW, MaxGard™), event MON863 x MON810 (Event Code MON-00863-5 x MON-00810-6, Commercially available as YieldGard™ Plus), event MON863 x MON810 x NK603 (Event Code MON-00603-6 x MON-00810-6 x MON-00863-5, Commercially available as YieldGard™ Plus with RR), event MON863 x NK603 (Event Code MON-00863-5 x MON- 00603-6, Commercially available as YieldGard™ RW + RR), event MON87427 x MON89034 x TC1507 x MON87411 x 59122 x DAS40278 (Event Code MON-87427-7 x MON-89034-3 x DAS-01507-1 x MON- 87411-9 x DAS-59122-7 x DAS-40278-9, Commercially available as SmartStax™ Pro x Enlist™), event MON88017 (Event Code MON-88017-3, Commercially available as YieldGard™ VT™ Rootworm™ RR2), event MON89034 (Event Code MON-89034-3, Commercially available as YieldGard™ VT Pro™), event MON89034 x MON88017 (Event Code MON-89034-3 x MON-88017-3, Commercially available as Genuity® VT Triple Pro™), event MON89034 x NK603 (Event Code MON-89034-3 x MON-00603-6, Commercially available as Genuity® VT Double Pro™,), event MON89034 x TC1507 x MON88017x 59122 (Event Code MON-89034-3 x DAS-01507-1 x MON-88017-3 x DAS-59122-7, Commercially available as Genuity® SmartStax™), event MON89034 x TC1507 x NK603 (Event Code MON-89034-3 x DAS- 01507-1 x MON-00603-6, Commercially available as Power Core™), event MON89034 x TC1507 x NK603 x MIR162 x DAS40278 (Event Code MON-89034-3 x DAS-01507-1 x MON-00603-6 x SYN- IR162-4 x DAS-40278-9, Commercially available as Power Core™ x MIR162 x Enlist™), event NK603 x MON810 (Event Code MON-00603-6 x MON-00810-6, Commercially available as YieldGard™ CB + RR), event T25 x MON810 (Event Code ACS-ZM003-2 x MON-00810-6, Commercially available as Liberty Link™ Yieldgard™ Maize), event TC1507 (Event Code DAS-01507-1 , Commercially available as Herculex™ I, Herculex™ CB), event TC1507 x 59122 x MON810 x MIR604 x NK603 (Event Code DAS- 01507-1 x DAS-59122-7 x MON-00810-6 x SYN-IR604-5 x MON-00603-6, Commercially available as Optimum™ Intrasect Xtreme), event TC1507 x 59122 (Event Code DAS-01507-1 x DAS-59122-7, Commercially available as Herculex XTRA™), event TC1507 x 59122 x MON810 x NK603 (Event Code DAS-01507-1 x DAS-59122-7 x MON-00810-6 x MON-00603-6, Commercially available as Optimum™ Intrasect XTRA), event TC1507 x 59122 x NK603 (Event Code DAS-01507-1 x DAS-59122-7 x MON- 00603-6, Commercially available as Herculex XTRA™ RR), event TC1507 x MIR604 x NK603 (Event Code DAS-01507-1 x SYN-IR604-5 x MON-00603-6, Commercially available as Optimum™ TRIsect), event TC1507 x MON810 x NK603 (Event Code DAS-01507-1 x MON-00810-6 x MON-00603-6, Commercially available as Optimum™ Intrasect), event TC1507 x NK603 (Event Code DAS-01507-1 x MON-00603-6, Commercially available as Herculex™ I RR).

[0099] Cultivated plants with increased yield have been created by using the transgene athb17 (e.g. corn event MON87403), or bbx32 (e.g. soybean event MON87712).

[0100] Tolerance to abiotic conditions, such as drought, has been created by using the transgene cspB (corn event MON87460) and Hahb-4 (soybean event IND-00410-5).

[0101] Examples of commercially available genetically modified corn, which can preferably be treated according to the invention, include, but are not limited to, commercially available products such as Enogen™, Agrisure® Duracade™, Agrisure® Duracade™ 5222, Agrisure™ CB / LL, Agrisure™ GT / CB / LL, Agrisure® Viptera™ 2100, Agrisure® Viptera™ 3110, Agrisure® Viptera™ 3100, Agrisure® Viptera™ 3111 , Agrisure® Viptera™ 4, Agrisure® Viptera™ 2100 Roundup Ready™ 2 Maize, Agrisure™ CB / LL / RW, Enlist™ Maize, Roundup Ready™ Maize, Agrisure™GT, Agrisure™ Viptera, Agrisure™ RW, YieldGard™, MaizeGard™, Roundup Ready™ Maize, SmartStax™ Pro x Enlist™, Genuity® DroughtGard™, YieldGard™ VT™ Rootworm™ RR2, YieldGard™ VT Pro™, Genuity® VT Triple Pro™, Genuity® VT Double Pro™, Genuity® SmartStax™, Power Core™, Power Core™ x MIR162 x Enlist™, Roundup Ready™ 2 Maize, YieldGard™ CB + RR, Roundup Ready™ Liberty Link™ Maize, Roundup Ready™ Liberty Link™ Enlist™ Maize, Liberty Link™ Maize, Herculex™ I, Herculex™ CB, Herculex XTRA™, Optimum™ Intrasect, or Herculex™ I RR.

[0102] The compound of formula (I), according to the invention may be used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they may be conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g., in polymeric substances. As with the type of the compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating, or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.

[0103] Suitable carriers and adjuvants, e.g., for agricultural use, can be solid or liquid and are substances useful in formulation technology, e.g., natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders, or fertilizers. Such carriers are for example described in WO 1997 / 33890.

[0104] Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended. Such formulations include anti-settling agents and dispersing agents and may further include a wetting agent to enhance activity as well an anti-foam and a crystal growth inhibitor. In use, these concentrates are diluted in water and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.

[0105] Wettable powders are in the form of finely divided particles which disperse readily in water or other liquid carriers. The particles contain the active ingredient retained in a solid matrix. Typical solid matrices include fuller’s earth, kaolin clays, silicas and other readily wet organic or inorganic solids. Wettable powders normally contain from 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.

[0106] Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquid and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate. Granular formulations include both extrudates and relatively coarse particles and are usually applied without dilution to the area in which treatment is required. Typical carriers for granular formulations include sand, fuller’s earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corn cobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulphate and other organic or inorganic materials which absorb or which can be coated with the active compound. Granular formulations normally contain 5% to 25% of active ingredients which may include surface-active agents such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils; and / or stickers such as dextrins, glue or synthetic resins.

[0107] Dusts are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours, and other organic and inorganic solids which act as dispersants and carriers.

[0108] The active ingredient, [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino] propanoate according to formula (I), and mixtures thereof with component (B) can also be contained in microcapsules. Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g., slow-release). Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight. The active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes can comprise, for example, natural or synthetic rubbers, cellulose, styrene / butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane, or chemically modified polymers, and starch xanthates, or other polymers that are known to the person skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.

[0109] Microcapsules are typically droplets or granules of the active ingredient enclosed in an inert porous shell which allows escape of the enclosed material to the surroundings at controlled rates. Encapsulated droplets are typically 1 to 50 microns in diameter. The enclosed liquid typically constitutes 50 to 95% of the weight of the capsule and may include solvent in addition to the active compound. Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form inside the granule pores. Granules typically range from 1 millimetre to 1 centimetre and preferably 1 to 2 millimetres in diameter. Granules are formed by extrusion, agglomeration or prilling, or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust, and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

[0110] Other useful formulations for agrochemical applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents. Pressurised sprayers, wherein the active ingredient is dispersed in finely divided form because of vaporisation of a low boiling dispersant solvent carrier, may also be used.

[0111] Suitable agricultural adjuvants and carriers that are useful in formulating the compositions of the invention in the formulation types described above are well known to a person skilled in the art.

[0112] Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetonalcohol, 1 ,2- dichloropropane, diethanolamine, p diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl formamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethyl acetate, 2-ethyl hexanol, ethylene carbonate, 1 , 1 , 1-trichloroethane, 2-heptanone, alpha pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octyl amine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol, and higher molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol, glycerine and N-methyl- 2-pyrrolidinone. Water is generally the carrier of choice for the dilution of concentrates.

[0113] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, fuller’s earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin.

[0114] A broad range of surface-active agents are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with carrier before application. These agents, when used, normally comprise from 0.1% to 15% by weight of the formulation. They can be anionic, cationic, non-ionic or polymeric in character and can be employed as emulsifying agents, wetting agents, suspending agents or for other purposes. Typical surface-active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulphate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C.sub. 18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C.sub. 16 ethoxylate; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium d i(2-ethy I hexy I ) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono and dialkyl phosphate esters. Other adjuvants commonly utilized in agricultural compositions include crystallisation inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, antifoaming agents, light-blocking agents, compatibilizing agents, antifoam agents, sequestering agents, neutralising agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants and sticking agents.

[0115] In addition, further, other biocidal active ingredients or compositions may be combined with the compounds or compositions of the invention and used in the methods of the invention and applied simultaneously or sequentially with the compounds or compositions of the invention. When applied simultaneously, these further active ingredients may be formulated together with the compounds or compositions of the invention or mixed in, for example, the spray tank. These further biocidal active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0116] Pesticidal agents are referred to herein using their common name are known, for example, from "The Pesticide Manual", 15th Ed., British Crop Protection Council 2009.

[0117] 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.

[0118] The compound of formula (I), according to the invention, is normally used in the form of agrochemical 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.

[0119] The compound of formula (I), according to the invention may be used in the form of (fungicidal) compositions for controlling or protecting against phytopathogenic microorganisms, comprising as active ingredient the compound as defined herein, in free form or in agrochemical usable salt form, and at least one of the above-mentioned adjuvants.

[0120] The invention therefore provides a composition, preferably a fungicidal composition, comprising the compound of formula (I), according to the invention, an agriculturally acceptable carrier and optionally an adjuvant. An agricultural acceptable carrier is for example a carrier that is suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, said composition may comprise at least one or more pesticidal-active compounds, for example an additional fungicidal active ingredient in addition to the compound of formula (I).

[0121] The compound of formula (I), according to the invention may be the sole active ingredient of a composition or it may be admixed with one or more additional active ingredients such as a pesticide, including fungicides, herbicide, insecticide, synergist, or plant growth regulator where appropriate. An additional active ingredient may, in some cases, result in unexpected synergistic activities. A further aspect of the present invention is a method of controlling diseases on useful crops or on propagation material thereof caused by phytopathogens, which comprises applying to the useful crops, the locus thereof or propagation material thereof a composition according to the invention. Preferred is a method, which comprises applying to the useful crops or to the locus thereof a composition according to the invention, more preferably to the useful crops. Further preferred is a method, which comprises applying to the propagation material of the useful crops a composition according to the invention.

[0122] Throughout this document the expression “composition” refers to the various mixtures or combinations of components (A) and (B), 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 when 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 components (A) and (B) is not essential for working the present invention.

[0123] The compositions according to the invention are effective against harmful microorganisms, such as microorganisms, that cause phytopathogenic diseases, in particular against phytopathogenic fungi and bacteria, more particular against phytopathogenic fungi, selected from Diaporthe species

[0124] Preferably, the formulation comprising a composition according to the invention may comprise of from 0.01 to 90% by weight of the composition comprising components (A) and (B), and of from 0 to 20% of an agriculturally acceptable surfactant. Preferably, the formulation further comprises other active agents, in particular microbiocides and pesticides, more generally.

[0125] Advantageously, the formulation further comprises of from 10 to 99.99% solid or liquid formulation inerts, conservatives and / or adjuvants.

[0126] The present invention preferably also relates to a concentrated composition for dilution by the user, comprising a composition according or a formulation according to the invention, comprising of from 2 to 80% by weight, preferably between 5 and 70% by weight, of active agents comprising at least a composition comprising (A) and (B), and optionally, other active agents.

[0127] The present invention preferably also relates to a seed dressing formulation for application to plant propagation materials, comprising a composition according to the invention, and further comprising a diluent. Preferably, the seed dressing formulation is in the form of an aqueous suspension or in a dry powder form having good adherence to the plant propagation materials. Preferably, the seed dressing formulation may comprise the active agents in an encapsulated form, preferably a slow-release capsules and / or microcapsules.

[0128] The present invention preferably also relates to a method of combating and controlling phytopathogens, comprising applying a fungicidally effective amount of a composition according to the invention to a pest, a locus of pest, or to a plant susceptible to attack by a pest, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practiced on the human or animal body.

[0129] The methods, compositions and uses according to any one of embodiments according to the invention are preferably for controlling or preventing infestation of the crop by the phytopathogenic fungi, selected from Diaporthe species, that are resistant to other fungicides. Phytopathogenic fungi, selected from Diaporthe species, that are "resistant" to a particular fungicide refer e.g. to strains of phytopathogenic fungi, selected from Diaporthe species that are less sensitive to that fungicide compared to the expected sensitivity of the same species of phytopathogenic fungi, selected from Diaporthe species. The expected sensitivity can be measured using e.g., a strain that has not previously been exposed to the fungicide.

[0130] An “effective” amount herein refers to an amount of the active ingredient that shows sufficient biocidal activity, e.g., at least 10 %, more preferably at least 20%, yet more preferably at least 50%, and again more preferably at least 70 % effectiveness, compared to the blind test.

[0131] In the present case, the composition according to the invention preferably comprise at least 0.01 ppm, more preferably at last 0.025 ppm of active ingredient, more preferably at least for example 6 ppm, 3 ppm, 2.2 ppm, 1.5 ppm, 0.8 ppm, 0.74 ppm, 0.25 ppm, 0.2 ppm, or 0.082 ppm as applied.

[0132] Application according to the methods or uses according to any one of embodiments according to the invention 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 as defined in any one of embodiments 1 to 13 can be performed according to any of the usual modes of application, e.g., foliar, drench, soil, in furrow etc.

[0133] The compounds as defined in any one of embodiments according to the invention are preferably used for pest control at rates of 1 to 500 g / ha, preferably 50-300 g / ha.

[0134] The compounds as defined in any one of embodiments according to the invention are suitable for use on any 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.

[0135] Generally, the compound as defined in any one of embodiments according to the invention is used in the form of a composition (e.g., formulation) containing a carrier. The compound as defined according to the invention 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.

[0136] Compositions of this invention, including all of the above disclosed embodiments and preferred examples thereof, 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 active compounds to form a multicomponent pesticide giving an even broader spectrum of agricultural protection. 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.

[0137] 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 compound of the invention, the grinding / milling of the compounds is to ensure specific particle size.

[0138] 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 the compound of formula (I) as defined herein and the type of composition is to be selected to suit the intended aims and the prevailing circumstances.

[0139] As a rule, the compositions comprise 0.1 to 99 %, especially 0.1 to 95 %, of component (A), and optionally component (B), as defined in any one of embodiments according to the invention 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.

[0140] With respect to compositions comprising component (A) and component (B); in general, the weight ratio of component (A) to component (B) is from 2000 : 1 to 1 : 1000. The weight ratio of component (A) to component (B) is preferably from 100 : 1 to 1 : 100; more preferably from 20 : 1 to 1 : 50, yet more preferably from 12 : 1 to 1 : 25; yet more preferably from 10 : 1 to 1 : 10, again more preferably from 5 : 1 to 1 : 15; and most preferably from 2 :1 to 1 : 5.

[0141] Besides a potential synergistic action with respect to fungicidal activity, the compositions according to the invention can also have further surprising advantageous properties. Examples of such advantageous properties that may be mentioned are: more advantageous degradability; improved toxicological and / or ecotoxicological behaviour; or improved characteristics of the useful crops including: emergence, crop yields, more developed root system, tillering increase, increase in plant height, bigger leaf blade, less dead basal leaves, stronger tillers, greener leaf colour, less fertilizers needed, less seeds needed, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth, improved plant vigour, and early germination. Additional beneficial effects can be the suppression or reduction of development of resistance against a certain active ingredient, by combinations that may have one or more different modes of action may in particular be beneficial.

[0142] Some compositions according to the invention have a systemic action and can be used as foliar, soil and seed treatment fungicides.

[0143] With the compositions according to the invention it is possible to inhibit or destroy the phytopathogenic microorganisms which occur in plants or in parts of plants (fruit, blossoms, leaves, stems, tubers, roots) in different useful crops, while at the same time the parts of plants which grow later are also protected from attack by phytopathogenic microorganisms.

[0144] The compositions according to the invention can be applied to the phytopathogenic microorganisms, the useful crops, the locus thereof, the propagation material thereof, storage goods or technical materials threatened by microorganism attack.

[0145] The compositions according to the invention may be applied before or after infection of the useful crops, the propagation material thereof, storage goods or technical materials by the microorganisms.

[0146] The amount of a composition according to the invention to be applied, will depend on various factors, such as the compounds employed; the subject of the treatment, such as, for example crops, soil or seeds; the type of treatment, such as, for example spraying, dusting or seed dressing; the purpose of the treatment, such as, for example prophylactic or therapeutic; the type of fungi to be controlled or the application time.

[0147] As used herein, the term “component (A)” refers to the compound of formula (I).

[0148] When applied to the useful crops the compound of formula (I) is typically applied at a rate of 5 to 2000 g a.i. / ha, particularly 10 to 1000 g a.i. / ha, particularly at a rate of 20 to 500 g a.i. / ha, particularly at a rate of 40 to 300 g a.i. / ha, particularly at a rate of 50 to 200 g a.i. / ha, e.g., 50, 60, 75, 80, 85, 90, 100 or 200 g a.i. / ha.

[0149] When applied to the useful crops the compound of formula (I) (component (A)) is typically applied at a rate of 5 to 200 g a.i. / ha, particularly 10 to 100 g a.i. / ha, particularly at a rate of 20 to 100 g a.i. / ha, particularly at a rate of 40 to 100 g a.i. / ha, particularly at a rate of 50 to 100 g a.i. / ha, e.g., 50, 60, 75, 80, 85, 90, 100 or 200 g a.i. / ha, preferably in association with 1 to 5000 g a.i. / ha, particularly 2 to 2000 g a.i. / ha, e.g., 100, 250, 500, 800, 1000, 1500 g a.i. / ha of component (B).

[0150] In one embodiment the compound of formula (I) is applied at a rate of from 5 to 200 g a.i. / ha, from 10 to 200 a.i. / ha, from 10 to 100 a.i. / ha, from 30 to 125 g a.i. / ha, from 40 to 110 g a.i. / ha, from 50 to 100 g a.i. / ha, from 60 to 95 g a.i. / ha. In another embodiment compound of formula (I) is applied at a rate of 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 100, 105, 110, 115, 120 or 125 g a.i. / ha.

[0151] In one embodiment component (A) (compound of formula (I)) is applied at a rate of 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 100, 105, 110, 115, 120 or 125 g a.i. / ha.

[0152] As used herein, “component (A)” refers to [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3- propanoyloxy-pyridine-2-carbonyl)amino] propanoate according to formula (I) as described herein. The term “g a.i. / ha” as used herein refer to the application rate given in gram [g] of active ingredient [a.i.] per unit of surface [ha]. The unit hectare (symbol ha) is the metric unit of area that equals a square with 100 m side (1 hm2) or 10,000 square meters. Hectare is a commonly used unit of area in the metric system.

[0153] In agricultural practice the application rates of the compositions according to the invention depend on the type of effect desired and typically range from 20 to 4000 g of total composition per hectare.

[0154] When the compositions according to the invention are used for treating seed, rates of 0.001 to 50 g of component (A) per kg of seed, preferably from 0.01 to 10 g per kg of seed, and preferably 0.001 to 50 g of a compound of component (B), per kg of seed, preferably from 0.01 to 10g per kg of seed, are generally sufficient.

[0155] Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.

[0156] When applied to the useful crops component (A) can typically applied as a formulated product at a rate of

[0157] 50 to 2000 ml_ f.p. / ha, particularly 100 to 1000 ml_ f.p. / ha, e.g., 50, 75, 100, 150, 200, 240, 260, or 300 ml_ f.p. / ha.

[0158] The term “ml_ f.p. / ha” as used herein refer to the application rate given in milliliter [mL] of formulated product [f. p. ] per unit of surface [ha]. The unit hectare (symbol ha) is the metric unit of area that equals a square with 100 m side (1 hm2) or 10,000 square meters. Hectare is a commonly used unit of area in the metric system.

[0159] As used herein, the term “formulated product” refers to the active ingredient in the formulation.

[0160] The compositions and formulations of the present invention can include the compound of formula (I) as the sole active ingredient in the compositions or formulations or can also be used in combination with other active ingredients, e.g., other fungicides, and / or insecticides, and / or acaricides, and / or nematicides, and / or molluscicides, and / or biologicals, and / or plant growth regulators.

[0161] The rates of application vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. As a general guideline compounds may be applied at a rate of from 1 to 2000 l / ha, especially from 10 to 1000 l / ha.

[0162] Preferred formulations can have the following compositions (weight %):

[0163] Emulsifiable concentrates: active ingredient: 1 to 95 %, preferably 60 to 90 % surface-active agent: 1 to 30 %, preferably 5 to 20 % liquid carrier: 1 to 80 %, preferably 1 to 35 %

[0164] Dusts: active ingredient: 0.1 to 10 %, preferably 0.1 to 5 % solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %

[0165] Suspension concentrates: active ingredient: 5 to 75 %, preferably 10 to 50 % water: 94 to 24 %, preferably 88 to 30 % surface-active agent: 1 to 40 %, preferably 2 to 30 %

[0166] Wettable powders: active ingredient: 0.5 to 90 %, preferably 1 to 80 % surface-active agent: 0.5 to 20 %, preferably 1 to 15 % solid carrier: 5 to 95 %, preferably 15 to 90 %

[0167] Granules: active ingredient: 0.1 to 30 %, preferably 0.1 to 15 % solid carrier: 99.5 to 70 %, preferably 97 to 85 %

[0168] The following Examples further illustrate, but do not limit, the invention.

[0169] Wettable powders a) b) c) active ingredients 25 % 50 % 75 % sodium lignosulfonate 5 % 5 % - sodium lauryl sulfate 3 % - 5 % sodium diisobutylnaphthalenesulfonate 6 % 10 % phenol polyethylene glycol ether (7-8 mol of ethylene oxide) 2 % highly dispersed silicic acid 5 % 10 % 10 %

[0170] Kaolin 62 % 27 % -

[0171] The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.

[0172] Powders for dry seed treatment a) b) c) active ingredients 25 % 50 % 75 % light mineral oil 5 % 5 % 5 % highly dispersed silicic acid 5 % 5 % Kaolin 65 % 40 % -

[0173] Talcum 20 %

[0174] The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.

[0175] Emulsifiable concentrate active ingredients 10 % octylphenol polyethylene glycol ether (4-5 mol of ethylene oxide) 3 % calcium dodecylbenzene sulfonate 3 % castor oil polyglycol ether (35 mol of ethylene oxide) 4 %

[0176] Cyclohexanone 30 % xylene mixture 50 %

[0177] Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water. Dusts a) b) c)

[0178] Active ingredients 5 % 6 % 4 %

[0179] Talcum 95 % -

[0180] Kaolin 94 % - mineral filler 96 %

[0181] Ready-for-use dusts are obtained by mixing the combination with the carrier and grinding the mixture in a suitable mill. Such dusts can also be used for dry dressings for seed.

[0182] Extruder granules

[0183] Active ingredients 15 % sodium lignosulfonate 2 % carboxymethylcellulose 1 %

[0184] Kaolin 82 %

[0185] The combination is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

[0186] Coated granules

[0187] Active ingredients 8% polyethylene glycol (mol. wt. 200) 3 %

[0188] Kaolin 89 %

[0189] The finely ground combination is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.

[0190] Suspension concentrates active ingredients 40 % propylene glycol 10 % nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 %

[0191] Sodium lignosulfonate 10 % carboxymethylcellulose 1 % silicone oil (in the form of a 75 % emulsion in water) 1 %

[0192] Water 32 %

[0193] The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

[0194] Flowable concentrate for seed treatment active ingredients 40 % propylene glycol 5 % copolymer butanol PO / EO 2 %

[0195] Tristyrenephenole with 10-20 moles EO 2 %

[0196] 1,2-benzisothiazolin-3-one (in the form of a 20% solution in water) 0.5 % monoazo-pigment calcium salt 5 %

[0197] Silicone oil (in the form of a 75 % emulsion in water) 0.2 %

[0198] Water 45.3 %

[0199] The finely ground combination is intimately mixed with the adjuvants, giving a flowable concentrate from which suspensions of any desired dilution can be obtained by dilution with water, that can be used directly for seed treatment. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

[0200] Slow Release Capsule Suspension

[0201] 28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate / polymethylene-polyphenylisocyanate-mixture (8:1 ). This mixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1 ,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed. The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The medium capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.

[0202] Formulation types include an emulsion concentrate (EC), a suspension concentrate (SC), a suspo- emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EC), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (CD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP), a soluble granule (SG) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0203] Various aspects and embodiments of the present invention will now be illustrated in more detail by way of example.

[0204] EXAMPLES

[0205] The Examples which follow serve to illustrate the invention and are not meant in any way to limit the invention. The compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by a person skilled in the art using the experimental procedures outlined in the Examples.

[0206] PREPARATION EXAMPLES

[0207] The preparation of the tests has been performed as follows:

[0208] Soybean pods with symptoms of “pod anomaly” were collected as follows: Isolates of Diaporthe ueckeri and Diaporthe longicolla from soybean were collected in the following Brazilian states: Parana (PR) (n = 3), Mato Grosso (MT) (n = 2), Mato Grosso do Sul (MS) (n = 2), Minas Gerais (MG) (n = 2), Para (PA) (n = 1 ). All the isolates collected in the cropping seasons of 2024 / 2025, were isolated from soybean pods and stem with symptoms of “anomaly”. Isolation was performed directly. Fragments of the fungus mycelium were removed from the soybean pods and were transferred to Petri dishes containing potato dextrose-agar (PDA) culture medium (4 g / L potato extract, 20 g / L dextrose, 15 g / L agar, pH 5.6 ± 0.2). The Diaporthe spp. were confirmed for each isolate based on colony and morphological characteristics.

[0209] The isolates were cultivated in PDA culture medium at 22°C under a photoperiod of 12 h / 12 h for 7 days. Petri dishes (Bipartite ) with 9 mm x 15 mm were used for this experiment. Each isolate was composed of four replicates. Mycelial discs with 4-mm diameter from the edge of the colonies were transferred to Petri dishes containing fungicide-amended PDA media. Petri dishes with PDA without fungicide treatments were used as control.

[0210] The following formulations were used: commercial and compound of formula (I) according to the present invention (Table 1)

[0211] Table 1 : Formulations used in the present invention

[0212] The formulations were diluted in sterile distilled water and homogenized in the PDA culture medium to a final concentration of 10 g / mL and homogenized in the PDA culture medium. The experiment was repeated twice, and the mean mycelia growth was averaged over the repetitions.

[0213] Different rates of each Al (A-11 , A-I2 and A-I4) were diluted in sterile distilled water and homogenized in the PDA culture medium.

[0214] After, Petri dishes were incubated at 24°C ± 2°C and 12 h / 12 h photoperiod for 5 days and the diameter of each colony was measured (orthogonal measurements) for each isolate to determine percentage of control by each fungicide compared to the growth on non-modified media (Check) following the methodology described by Ishii H. et al. Pest Manag. Sei. 2009, 65, 916-922. The percentage control by the fungicide was calculated from the growth on modified media compared to growth on PDA (Mello F. E. et al., Trop. plant pathol. 2021 46, 69-80).

[0215] Table 2: Percentage [%] of control based on mycelial growth at different concentrations (from 0.001 to 100ppm) for A-11

[0216] Table 3: Percentage [%] of control based on mycelial growth at different concentrations (from 0.001 to 100ppm) for A-12 Table 4: Percentage [%] of control based on mycelial growth at different concentrations (from 0.001 to

[0217] 100ppm) for A-14

[0218] The results in above tables (table 2 to table 4) clearly show differences in the level of control compared to those active ingredients A-11 , A-I2 and A-I4 tested. Compound A-I4 showed the highest level of control, reaching 97% on average of ten Diaporthe spp. isolates tested at concentration of 100 ppm, compared to 11 % control for A-l 1 or 8% control for A-I2.

Claims

CLAIMS1. A method of combating, preventing or controlling Diaporthe species, which comprises applying to a crop of soybean, the locus thereof, or propagation material thereof, [(1S,2S)-1-methyl-2-(o- tolyl)propy I] (2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino] propanoate according to formula (I)(I).

2. The method according to claim 1, wherein the Diaporthe species comprise at least one of the species selected from Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, Diaporthe longicolla, Diaporthe masirevicii, and Diaporthe pyracanthae.

3. The method according to any one of the precedent claims, wherein the Diaporthe species comprise at least two of the species selected from Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, Diaporthe longicolla, Diaporthe masirevicii, and Diaporthe pyracanthae.

4. The method according to any one of the precedent claims, wherein the Diaporthe species comprise at least three of the species selected from Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, Diaporthe longicolla, Diaporthe masirevicii, and Diaporthe pyracanthae.

5. The method according to any one of the precedent claims, wherein the Diaporthe species comprise Diaporthe miriciae, Diaporthe sojae or Diaporthe macadamiae, or a combination thereof.

6. The method according to any one of the precedent claims, wherein the compound of formula (I) is applied at a rate of 5 to 200 g a.i. / ha, and preferably at a rate of 10 to 100 g a.i. / ha.

7. The method according to any one of the precedent claims, wherein the soybean crop is a crop of transgenic crops.

8. The method according to claim 7, wherein said transgenic crop is selected from Bt soybean plants.

9. The method according to any one of the precedent claims, wherein the compound of formula (I) is applied in combination with a fungicidally active compound.

10. A method of combating, preventing or controlling Diaporthe species, which comprises applying to a crop of soybean, the locus thereof, or propagation material thereof, a mixture of components (A) and(B) as active ingredients, wherein component (A) is [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino] propanoate according to formula (I)(i); and component (B) is a compound selected from the group consisting of benzovindiflupyr, bifemetstrobin, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole, metconazole, tetraconazole, fluoxytioconazole, flufenoxadiazam, 2-[2-chloro-4-(4- chlorophenoxy)phenyl]-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propanoate, methyl 3-[(4-chlorophenyl)- methyl]-2-hydroxy-1-methyl-2-(1 ,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate, flutriafol, mefentri- fluconazole, ipconazole, paclobutrazol, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metalaxyl-M, fenpropidin, fenpropimorph, cyprodinil, spiroxamine, mancozeb, chlorothalonil, folpet, copper-oxychloride, copper-hydroxide, sulphur, oxathiapiprolin, ipflufenoquin, quinofumelin, mandipropamid, fluazinam, fludioxonil, fosetyl-aluminium, acibenzolar-S-methyl, enestrobin, inpyrfluxam, fluindapyr, isoflucypram, metyltetraprole, florylpicoxamid, feneptamidoquin, metcyclofenstrobin, isofetamid, procymidone, carbendazim, fenhexamid, prochloraz, prohexadione- calcium, melaluca alternifolia oil, N-methoxy-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl]methyl]propanamide, 3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4- yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1 ,2,4-oxadiazine, cyclobutrifluram, calcium phosphonate, cis-jasmone, trinexapac-ethyl, glyphosate, 2,4-D (2,4-dichlorophenoxyacetic acid) and thiamethoxam.

11. Use of the compound of formula (I) as defined in claim 1 or a mixture as defined in claim 10, to control Diaporthe species in soybeans.

12. Use according to claim 11 , wherein the Diaporthe species comprise at least one of the species selected from Diaporthe miriciae, Diaporthe sojae, Diaporthe macadamiae, Diaporthe longicolla, Diaporthe masirevicii, and Diaporthe pyracanthae.

13. Use according to claim 12, wherein the Diaporthe species comprise at least Diaporthe miriciae.

14. Use according to claim 12 or 13, wherein the Diaporthe species comprise at least Diaporthe miriciae, and Diaporthe sojae.

15. Use according to any one of claims 12 to 14, wherein the Diaporthe species comprise at least Diaporthe miriciae, Diaporthe sojae or Diaporthe macadamiae, or a combination thereof.

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