Method for controlling or preventing infestation of plants by plant pathogenic microorganism corynespora cassiicola

Abstract

The present invention relates to a method for controlling or preventing infestation of plants by the phytopathogenic microorganism Corynespora cassiicola, the method comprises applying a fungicidally effective amount of a compound as defined in claim 1, an N-oxide or an agriculturally acceptable salt thereof to a plant pathogen, a locus of the plant pathogen, or a plant susceptible to attack by the plant pathogen, or propagation material thereof.

Description

[0001] This invention relates to methods for controlling or preventing plant infection by plant pathogenic microorganisms. Corynebacterium multiflorum ( Corynespora cassiicola Methods of infection.

[0002] Corynebacterium multiflorum Infecting more than 530 species from 53 families (Dixon, LJ et al.) Phytopathology [ Plant pathology [2009, 99(9), 1015-27]. It is most common in tropical and subtropical regions. It has also been isolated from nematodes and human skin. Corynebacterium multiflorum It is considered a pathogen of many crops, such as soybeans, corn, wheat, cotton, beans, potatoes, sweet potatoes, and tobacco. On several plants, it is caused by… Corynebacterium multiflorum The resulting disease is called target leaf spot or target spot disease, such as soybean target leaf spot and cotton target leaf spot.

[0003] One or more plant pathogens Corynebacterium multiflorum Resistance to many current commercial solutions limits their effectiveness, and while the development of new agrochemical fungicides is underway, many of these new chemicals have limitations in their fungicidal spectrum and can only control certain specific plant pathogens. That is, when a new chemical is proven to control certain plant pathogens on certain crops, it cannot be expected that the same chemical will be proven to control plant pathogens. Corynebacterium multiflorum For example, on soybeans or cotton.

[0004] Therefore, there is a need to develop methods for controlling or preventing plant damage caused by plant pathogens. Corynebacterium multiflorum A novel method of infection, wherein the plant is selected from corn, cotton, and soybean, preferably soybean. In one embodiment, the plant is a genetically modified plant, preferably a Bt plant, more preferably a Bt soybean plant, Bt cotton, or Bt corn.

[0005] WO 2017 / 055473 discloses that certain oxadiazole derivatives have antimicrobial activity, especially antifungal activity.

[0006] Agricultural chemical compositions containing oxadiazole compounds have been substantially disclosed in WO 2017 / 055473. Mixtures of this compound with fungicides are disclosed in WO 2018 / 177894, WO 2022117653 A1, WO 2022106304 and WO2022117373. Methods for preparing oxadiazole compounds have been disclosed in WO 2018 / 177894 and WO 2020 / 212513.

[0007] It has now been unexpectedly discovered that the specific oxadiazole compounds disclosed in WO 2017 / 055473 are effective in controlling or preventing plant pathogenic microorganisms in the family Corynebacterium, particularly... Corynebacterium multiflorum They are highly effective in controlling infection. Therefore, these highly effective compounds provide farmers with a means to control or prevent plant infection by plant pathogenic microorganisms. Corynebacterium multiflorum Infection offers an important new solution.

[0008] Furthermore, it has now been unexpectedly discovered that the specific oxadiazole compounds disclosed in WO 2017 / 055473 are effective in controlling or preventing plant pathogenic microorganisms of the Cladosporaceae family on soybean plants, particularly... Corynebacterium multiflorum They are highly effective against infection. Therefore, these highly effective compounds provide farmers with a means to control or prevent soybean plants from being infected by plant pathogenic microorganisms. Multi-master Spores Infection offers an important new solution.

[0009] Additionally, it has now been unexpectedly discovered that the specific oxadiazole compounds disclosed in WO 2017 / 055473 are effective in controlling or preventing plant pathogenic microorganisms of the Cladosporaceae family in genetically modified soybean plants, particularly... Corynebacterium multiflorum They are highly effective against infection. Therefore, these highly effective compounds provide farmers with a means to control or prevent genetically modified soybean plants (like Bt soybean plants) from being infected by plant pathogens. Multi-master corynebacterium Infection offers an important new solution.

[0010] Furthermore, it has now been unexpectedly discovered that the specific oxadiazole compounds disclosed in WO 2017 / 055473 are effective in controlling or preventing plant pathogenic microorganisms of the Cotyledonaceae family, particularly... Corynebacterium multiflorum They are highly effective against infection. Therefore, these highly effective compounds provide farmers with a means to control or prevent plant pathogens from infecting cotton. Corynebacterium multiflorum Infection offers an important new solution.

[0011] Additionally, it has now been unexpectedly discovered that the specific oxadiazole compounds disclosed in WO 2017 / 055473 are effective in controlling or preventing plant pathogenic microorganisms of the Corynebacteriumceae family in genetically modified cotton, particularly... Corynebacterium multiflorum They are highly effective against infection. Therefore, these highly effective compounds provide farmers with a means to control or prevent genetically modified cotton (like Bt cotton) from being infected by plant pathogens. Corynebacterium multiflorum Infection offers an important new solution.

[0012] Additionally, it has now been unexpectedly discovered that specific oxadiazole compounds are effective in controlling or preventing plant pathogens of the Cladosporaceae family, particularly in the control or prevention of plant growth in the field. Multi-master corynebacteriumThey are highly effective in controlling infection. Therefore, these highly effective compounds provide farmers with a means to control or prevent plant pathogens from infecting plants in the field. Corynebacterium multiflorum Infection offers an important new solution.

[0013] Additionally, it has now been unexpectedly discovered that pest control compositions containing specific oxadiazole compounds and one or more formulation adjuvants are effective in controlling or preventing plant, particularly field-grown, plant pathogens of the Cladosporaceae family, especially... Corynebacterium multiflorum They are highly effective against infection. Therefore, these highly effective pest control compositions provide farmers with a means to control or prevent the spread of plant pathogens, especially those growing in the field. Corynebacterium multiflorum Infection offers an important new solution.

[0014] In particular, it has been unexpectedly found that, when applied in the field, specific oxadiazole compounds and pest-killing compositions as defined herein exhibit greater activity against the same plant pathogens compared to their activity when applied in liquid culture, especially compared to the relative activity of active ingredients from commercial products in liquid culture. Corynebacterium multiflorum It is more effective in preventing infection.

[0015] According to a first aspect of the present invention, a method for controlling or preventing plant pathogenic microorganisms is provided. Multi-master Spores Methods of infection, comprising applying to a plant pathogen, the site of the plant pathogen, or a plant susceptible to the plant pathogen, or its propagation material, a fungicide-effective amount of a compound of formula (I) or its agrochemically acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof.

[0016] (I)

[0017] in

[0018] R 1 Selected from C1-C4-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, C3-C6-cycloalkyl, or C1-C2-alkoxy-C1-C3-alkyl;

[0019] R 2 Selected from hydrogen or C1-C2-alkoxy groups;

[0020] R 3 R 4 Independently selected from hydrogen or C1-C4-alkyl; and

[0021] R 5 Selected from C1-C2-halogenated alkyl groups.

[0022] According to a second aspect of the present invention, a method for controlling or preventing plant infection by plant pathogenic microorganisms is provided. Multi-master Spores A method of infection, comprising applying to a plant pathogen, a site of the plant pathogen, a plant susceptible to the plant pathogen, or its propagation material a pest-killing composition comprising a compound having formula (I) and one or more formulation adjuvants.

[0023] In a preferred embodiment, a pest control composition comprising a compound of formula (I) or a compound of formula (I) and one or more formulation adjuvants is applied in the field.

[0024] According to a third aspect of the present invention, a method for controlling or preventing plant pathogenic microorganisms in field-grown plants is provided. Corynebacterium multiflorum A method of infection, comprising applying to a plant pathogen, a site of the plant pathogen, or a plant susceptible to the plant pathogen, or its propagation material a compound having formula (I) or a pest-killing composition comprising a compound having formula (I) and one or more formulation adjuvants, formulation auxiliaries, diluents, and / or carriers.

[0025] According to a fourth aspect of the present invention, a method according to any one of the above embodiments is provided, the method comprising the steps of: providing a composition comprising a compound having formula (I); applying the composition to a propagating material; and planting the propagating material.

[0026] According to a fifth aspect of the present invention, a method according to any one of the above embodiments is provided, the method comprising the steps of: providing a composition comprising a compound having formula (I); and applying the composition to a plant pathogen, a site of the plant pathogen, or a plant susceptible to the plant pathogen.

[0027] Preferably, in these aspects of the invention, the pest-killing composition comprises at least one or more formulation adjuvants, as well as one or more formulation auxiliaries, diluents, and / or carriers.

[0028] According to a sixth aspect of the invention, a compound having formula (I) is provided for controlling or preventing plant infection by plant pathogenic microorganisms. Corynebacterium multiflorum Uses of contamination.

[0029] According to a seventh aspect of the invention, a method or use according to any one of the embodiments described above is provided, wherein the plant is selected from legumes, cowpeas, cucumbers, papayas, soybeans, potatoes, sweet potatoes, tomatoes, cotton, corn, wheat, tobacco, eggplants, basil, thyme, rubber trees, papaya trees, azaleas, and hydrangeas.

[0030] According to an eighth aspect of the invention, a method or use according to any one of the embodiments described above is provided, wherein the plant is selected from soybean, corn, wheat, cotton, legumes, potato, sweet potato, and tobacco.

[0031] According to a ninth aspect of the invention, a method or use according to any one of the foregoing embodiments is provided, wherein the plants are genetically modified plants, preferably Bt plants.

[0032] According to a tenth aspect of the invention, the invention preferably also relates to a pest-killing composition suitable for controlling diseases caused by plant pathogens, the pest-killing composition comprising a component (A) and at least one or more compounds (B), wherein the component A is a compound having formula (I).

[0033] (I)

[0034] Where R 1 Selected from C1-C4-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, C3-C6-cycloalkyl, or C1-C2-alkoxy-C1-C3-alkyl; R 2 Selected from hydrogen or C1-C2-alkoxy; R 3 R 4 Independently selected from hydrogen or C1-C4-alkyl; and R 5 The compound (B) is selected from C1-C2-haloalkyl; and the at least one or more of the compounds (B) are selected from other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides, one or more adjuvants, and diluents or carriers, or formulation adjuvants, or combinations thereof.

[0035] According to an eleventh aspect of the invention, the invention preferably also relates to a pest-killing composition suitable for controlling diseases caused by plant pathogens, the pest-killing composition comprising a component (A) and at least one or more compounds (B), wherein the component A is a compound having formula (I).

[0036] (I)

[0037] Where R 1 Selected from C1-C4-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, C3-C6-cycloalkyl, or C1-C2-alkoxy-C1-C3-alkyl; R 2 Selected from hydrogen or C1-C2-alkoxy; R 3 R 4Independently selected from hydrogen or C1-C4-alkyl; and R 5 The compound is selected from C1-C2-haloalkyl groups; and the at least one or more of the compounds (B) are selected as suicide toxic agents.

[0038] A compound having at least one basic center of formula (I) can form, for example, an acid addition salt with: a strong inorganic acid, such as a mineral acid, such as perchloric acid, sulfuric acid, nitric acid, nitrous acid, phosphoric acid, or hydrohalic acid; a strong organic carboxylic acid, such as an unsubstituted or, for example, halogenated C1-C4-alkylcarboxylic acid, such as acetic acid; a saturated or unsaturated dicarboxylic acid, such as oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, or phthalic acid; a hydroxycarboxylic acid, such as ascorbic acid, lactic acid, malic acid, tartaric acid, or citric acid; or an organic sulfonic acid, such as an unsubstituted or, for example, halogenated C1-C4-alkylsulfonic acid or arylsulfonic acid, such as methanesulfonic acid or p-toluenesulfonic acid. A compound having at least one acidic group of formula (I) may, for example, form a salt with a base, such as a mineral salt, like an alkali metal or alkaline earth metal salt, such as a sodium salt, potassium salt or magnesium salt; or form a salt with ammonia or an organic amine (such as morpholine, piperidine, pyrrolidine, mono-, di- or tri-alkylamines, such as ethylamine, diethylamine, triethylamine or dimethylpropylamine, or mono-, di- or tri-hydroxyalkylamines, such as monoethanolamine, diethanolamine or triethanolamine).

[0039] In each case, the compound having formula (I) according to the invention is in free form, oxidized form (as an N-oxide), or salt form (e.g., an agronomically usable salt form). The N-oxide is an oxidized form of a tertiary amine or an oxidized form of a nitrogen-containing heteroaromatic compound. For example, in A. Albini and S. Pietra's book "Heterocyclic N-oxides"... They are described in "[Heterocyclic N-oxides]", CRC Press, Boca Raton, 1991.

[0040] The compounds of formula (I) according to the invention also include hydrates that may form during salt formation.

[0041] When substituents are indicated as "optionally substituted," this means they may or may not have one or more of the same or different substituents, for example, one, two, or three R. xSubstituents. For example, C1-C6-alkyl groups substituted with one, two, or three halogens may include, but are not limited to, -CH2Cl, -CHCl2, -CCl3, -CH2F, -CHF2, -CF3, -CH2CF3, or -CF2CH3 groups. As another example, C1-C6-alkoxy groups substituted with one, two, or three halogens may include, but are not limited to, CH2ClO-, CHCl2O-, CCl3O-, CH2FO-, CHF2O-, CF3O-, CF3CH2O-, or CH3CF2O- groups. Further, as used herein, the term "optionally substituted" may be used interchangeably with the term "unsubstituted or substituted".

[0042] As used herein, the term "halogen" or "halogen group" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo), or iodine (iodo), preferably fluorine, chlorine, or bromine. This also applies accordingly to halogens combined with other meanings, such as halogenated alkyl, halogenated alkenyl, halogenated alkynyl, halogenated alkoxy, and halogenated cycloalkyl.

[0043] As used in this article, the term "C1-C" n "-alkyl" refers to a saturated straight-chain or branched hydrocarbon group having 1 to n carbon atoms attached via any one of the carbon atoms, such as, but not limited to, methyl, ethyl, n-propyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1-dimethylpropyl, 1,2-dimethylpropyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or 1-ethyl-2-methylpropyl.

[0044] As used in this article, the term "C3-C" n "-cycloalkyl" refers to tri(3) to n-membered cycloalkyl groups, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

[0045] As used in this article, the term "C1-C" n "-alkoxy" refers to a straight-chain or branched saturated alkyl group (as mentioned above) having one (1) to n carbon atoms attached via an oxygen atom, i.e., any one of the following groups: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy.

[0046] As used in this article, the term "C1-C" n"-Halogenated alkyl" refers to a straight-chain or branched saturated alkyl group (as mentioned above) having 1 to n carbon atoms attached via any one carbon atom, wherein some or all of the hydrogen atoms in these groups may be replaced by fluorine, chlorine, bromine and / or iodine, i.e., for example, but not limited to chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, or 2-chloro-2-fluoroethyl.

[0047] As used in this article, the term "C1-C" n -alkoxy-C1-C n "-alkyl" refers to a compound formed by C1-C2. n -Alkoxy-substituted alkyl groups (as mentioned above). Examples are, but are not limited to, methoxymethyl, methoxyethyl, ethoxymethyl, and propoxymethyl.

[0048] As used herein, the term “control” means reducing the number of pests, eliminating pests and / or preventing further pest damage, thereby reducing damage to plants or plant-derived products.

[0049] As used herein, the term "pest" refers to insects and mollusks found in the storage of agricultural, horticultural, forestry, and plant-derived products (such as fruits, grains, and timber); as well as pests associated with damage to man-made structures. The term "pest" encompasses all stages of the pest life cycle.

[0050] As used herein, the term "effective amount" refers to the amount of a compound or its salt that provides the desired effect when applied in a single or multiple applications.

[0051] The effective amount is readily determined by those skilled in the art using known techniques and by observing results obtained under similar conditions. In determining the effective amount, numerous factors are considered, including but not limited to, the type of plant or derivative to be applied; the pest to be controlled and its life cycle; the specific compound applied; the type of application; and other relevant circumstances.

[0052] As used herein, the terms “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.

[0053] The following list provides the substituents R of compounds having formula (I) according to the present invention. 1 R 2 R 3 R 4 and R 5The definitions, including preferred definitions, are provided below. Any definition given below for any of these substituents may be combined with any definition of any other substituent given below or elsewhere in this document.

[0054] In one embodiment of the present invention, R 1 Selected from C1-C4-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, C3-C6-cycloalkyl, or C1-C2-alkoxy-C1-C3-alkyl. Preferably, R 1 It is a C3-C6-cycloalkyl or a C1-C2-alkoxy-C1-C3-alkyl. More preferably, R 1 It is cyclopropyl or 1-methoxyethyl.

[0055] In one embodiment of the present invention, R 2 Selected from hydrogen or C1-C2-alkoxy groups. Preferably, R 2 Selected from C1-C2-alkoxy groups. More preferably, R 2 It is a methoxy group.

[0056] In one embodiment of the present invention, R 3 R 4 Independently selected from hydrogen or C1-C4-alkyl. Preferably, R 3 R 4 Independently selected from hydrogen or methyl. More preferably, R 3 R 4 It is hydrogen.

[0057] In one embodiment of the present invention, R 5 Selected from C1-C2-haloalkyl groups. Preferably, R 5 Selected from dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, or chlorodifluoromethyl. More preferably, R 5 It is trifluoromethyl or dichlorofluoromethyl. Even more preferably, R 5 It is trifluoromethyl.

[0058] Therefore, the present invention makes it possible to obtain compounds having formula (I) that have R as defined above in all combinations / permutations. 1 R 2 R 3 R 4 and R 5 .

[0059] Embodiments of the present invention are provided, as listed below.

[0060] In one embodiment of the invention, the compound having formula (I) is selected from N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide according to structure IA; or

[0061] (IA)

[0062] Based on the structure IB, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acrylamide

[0063] (IB).

[0064] In a preferred embodiment of the invention, the compound having formula (I) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide according to structure IA.

[0065] In another preferred embodiment of the invention, the compound having formula (I) is N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acrylamide according to structure IB.

[0066] Those skilled in the art know that, according to the method of the present invention, one or more compounds are typically applied as part of a pest-killing composition.

[0067] Agricultural chemical compositions comprising the oxadiazole compound have been substantially disclosed in WO 2017 / 055473. Mixtures of this compound with fungicides are disclosed in WO 2018 / 177894, WO 2022117653 A1, WO 2022106304, and WO 2022117373. Methods for preparing the oxadiazole compound have been disclosed in WO 2018 / 177894 and WO 2020 / 212513.

[0068] In one embodiment of the invention, a composition comprising a compound having formula (I) is provided for controlling or preventing plant infection by plant pathogenic microorganisms. Corynebacterium multiflorum Infection. The plant is selected from corn, cotton, and soybean, preferably soybean. In one embodiment, the plant is a genetically modified plant, preferably a Bt plant, more preferably a Bt soybean plant, Bt cotton, or Bt corn.

[0069] Such biocidal compositions typically contain one or more adjuvants, formulation aids, diluents, and / or carriers as described in detail below, preferably at least one or more adjuvants.

[0070] In another embodiment of the invention, a composition is provided comprising a compound having formula (I) and preferably one or more adjuvants, formulation auxiliaries, diluents, and / or carriers for controlling or preventing plant damage caused by plant pathogenic microorganisms. Corynebacterium multiflorum Infection includes the following steps: providing a composition comprising the compound having formula (I); and applying the composition to a plant pathogen, a site of the plant pathogen, or a plant susceptible to the plant pathogen.

[0071] In one embodiment of the present invention, a fungicidal composition is provided comprising a mixture of component (A) and component (B) as an active ingredient, wherein component (A) is selected from compounds having formula (I), (IA), or (IB), and component (B) is selected from compounds including: benzo[a]fluopyram, fluopyram, fluopyram, pyraclostrobin, fluopyram, pyraclostrobin, fluopyram, bifenthionil, difenoconazole, cyclophosphamide, tebuconazole, hexaconazole, prothioconazole, propiconazole, fluopyram, tebuconazole, tetraflufenazole, fluopyram, fenbendazole, chlorfluazuron, styraclostrobin, paclobutrazol, azoxystrobin, oxadiazon, and difenoconazole. Azoxystrobin, azoxystrobin, metalaxyl-M, benzyl sulfide, butyl morpholine, pyraclostrobin, spirocyclam, mancozeb, chlorothalonil, captan, copper oxychloride, copper hydroxide, sulfur, fluoxadixyl acetamiprid, isopropylquinoline, fluopyram, dimethomorph, fluazinam, fluazinam, fosetyl-aluminum, aramid-S-methyl, tebufenozide, indapoxetine, fluopyram, isopropylfluopyram, tetrazolium Pyridine amide, pyridine oxadixyl, fluoxadixyl, isoprothiolane, iprodione, carbendazim, cyclophosphamide, prochloraz, calcium cyclophosphamide, trifluoropyridine amide, calcium phosphite, cis-jasmone, anti-rot ester, glyphosate, 2,4-dichlorophenoxyacetic acid, thiamethoxam, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate, 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate, (Z)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoic acid methyl ester, (E)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoic acid methyl ester (this compound can be derived from JP) (Prepared by the method described in 2023078251); (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (this compound can be prepared by WO Prepared by the method described in 2020 / 193387); (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; (5S)-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; 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 (these compounds can be prepared by WO Prepared by the method described in WO 2020 / 127780 and WO 2021 / 255070).Or Melaleuca alternifolia leaf oil (an extract of the tea plant Melaleuca alternifolia (commercially available as Timorx Gold®, a broad-spectrum plant-derived biofungicide)), or its salts, enantiomers, tautomers, or N-oxides, for the control or prevention of plant pathogenic microorganisms. Corynebacterium multiflorum Infection. Preferably, the plant is selected from cotton, corn, or soybean. In one embodiment, the plant is a genetically modified plant, preferably a Bt plant, more preferably a Bt soybean plant, Bt cotton, or Bt corn.

[0072] In a preferred composition according to this aspect of the invention, component (A) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazon-3-yl]phenyl]methyl]cyclopropaneformamide (compound IA), or a salt thereof, enantiomer, tautomer, or N-oxide, and component (B) is selected from benzo[a]fluorobenzoxazole, fluopyram, fluopyram, pyraclostrobin, fluopyram, pyraclostrobin, fluopyram, bifenthionil, difenoconazole, cycloconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, fluopyram, tebuconazole, tetraflufenazole, fluopyram, fenpyroxabin, chlorfluazuron, styraclostrobin, paclobutrazol, azoxystrobin, oxadiazon, pyrimethanil, and pyraclostrobin. Ester, Metalaxyl-M, Benzoyl sulfide, Butylmorpholine, Azoxystrobin, Spirocyclohexane, Mancozeb, Chlorothalonil, Captan, Copper oxychloride, Copper hydroxide, Sulfur, Fluopyram, Isopropylquinoline, Fluopyram, Dipyridamole, Fluazinam, Fludioxonil, Fosetyl-aluminum, Aramacin-S-methyl, Enoxaflutole, Indexpyram, Fluopyram, Isopropylfluopyram, Tetracycline, Pyridaben Amide, pyridine oxadixyl, fluoxadixyl, isoprothiolane, iprodione, carbendazim, cyclophosphamide, prochloraz, calcium cyclophosphamide, trifluoropyridine amine, calcium phosphite, cis-jasmone, anti-rot ester, glyphosate, 2,4-dichlorophenoxyacetic acid, thiamethoxam, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate, 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate, (Z)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoic acid methyl ester, (E)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoic acid methyl ester (this compound can be derived from JP) (Prepared by the method described in 2023078251); (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (this compound can be prepared by WO Prepared by the method described in 2020 / 193387); (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; (5S)-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; 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 (these compounds can be prepared by WO Prepared by the method described in WO 2020 / 127780 and WO 2021 / 255070).Or Melaleuca alternifolia leaf oil (an extract of the tea plant Melaleuca alternifolia (commercially available as Timorx Gold®, a broad-spectrum plant-derived biofungicide)), or its salts, enantiomers, tautomers, or N-oxides, for the control or prevention of plant pathogenic microorganisms. Corynebacterium multiflorum Infection. Preferably, the plant is selected from cotton, corn, or soybean. In one embodiment, the plant is a genetically modified plant, preferably a Bt plant, more preferably a Bt soybean plant, Bt cotton, or Bt corn.

[0073] In another preferred composition according to the invention, component (A) is N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acrylamide (compound IB), or a salt, enantiomer, tautomer, or N-oxide thereof, and component (B) is selected from benzo[a]fluorobenzoxazole, fluopyram, fluopyram, pyraclostrobin, fluopyram, pyraclostrobin, fluopyram, bifenthionil, difenoconazole, cyclophosphamide, tebuconazole, hexaconazole, prothioconazole, propiconazole, fluopyram, tebuconazole, tetraflufenazole, fluopyram, fenpyroxacin, chlorfluazuron, styraclostrobin, paclobutrazol, azoxystrobin, oxadiazon, pyraclostrobin, and pyraclostrobin. Ester, Metalaxyl-M, Benzoyl sulfide, Butylmorpholine, Azoxystrobin, Spirocyclohexane, Mancozeb, Chlorothalonil, Captan, Copper oxychloride, Copper hydroxide, Sulfur, Fluopyram, Isopropylquinoline, Fluopyram, Dipyridamole, Fluazinam, Fludioxonil, Fosetyl-aluminum, Aramacin-S-methyl, Enoxaflutole, Indexpyram, Fluopyram, Isopropylfluopyram, Tetracycline, Pyridaben Amide, pyridine oxadixyl, fluoxadixyl, isoprothiolane, iprodione, carbendazim, cyclophosphamide, prochloraz, calcium cyclophosphamide, trifluoropyridine amine, calcium phosphite, cis-jasmone, anti-rot ester, glyphosate, 2,4-dichlorophenoxyacetic acid, thiamethoxam, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate, 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate, (Z)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoic acid methyl ester, (E)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoic acid methyl ester (this compound can be derived from JP) (Prepared by the method described in 2023078251); (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (this compound can be prepared by WO Prepared by the method described in 2020 / 193387); (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; (5S)-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; 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 (these compounds can be prepared by WO Prepared by the method described in WO 2020 / 127780 and WO 2021 / 255070).Or Melaleuca alternifolia leaf oil (an extract of the tea plant Melaleuca alternifolia (commercially available as Timorx Gold®, a broad-spectrum plant-derived biofungicide)), or its salts, enantiomers, tautomers, or N-oxides, for the control or prevention of plant pathogenic microorganisms. Corynebacterium multiflorum Infection. Preferably, the plant is selected from cotton, corn, or soybean. In one embodiment, the plant is a genetically modified plant, preferably a Bt plant, more preferably a Bt soybean plant, Bt cotton, or Bt corn.

[0074] Typically, the weight ratio of component (A) to component (B) can be 1000:1 to 1:1000, 100:1 to 1:100, preferably 50:1 to 1:50, more preferably 20:1 to 1:40, even more preferably 15:1 to 1:30, still more preferably 12:1 to 1:25, or 10:1 to 1:20, or 10:1 to 1:10, or 5:1 and 1:15, or 5:1 to 1:5, or 4:1 to 1:4, or 3:1 to 1:10, or 3:1 to 1:3, or 2:1 to 1:5, or 1:1.

[0075] In any composition according to the invention, the composition may contain an additional active ingredient component (C), which is different from component (B) and is selected from benzo[a]fluopyram, fluopyram, fluopyram hydroxylamine, pyraclostrobin, fluopyram, pyraclostrobin, fluopyram, bifenthionil, difenoconazole, cyclophosphamide, tebuconazole, hexaconazole, prothioconazole, propiconazole, fluopyram, tebuconazole, tetrafluopyram, and fluopyram. Azoxystrobin, fenbendazole, chlorfluazuron, sphalosporin, paclobutrazol, azoxystrobin, oxadiazon, azoxystrobin, pyraclostrobin, metalaxyl-M, benzyl sulfadiazine, butyl morpholine, pyraclostrobin, spirocyclam, mancozeb, chlorothalonil, captan, copper oxychloride, copper hydroxide, sulfur, fluopyram, isopropyl quinoline, fluopyram, dimethomorph, fluazinam, fluazinam, fosetyl-aluminum, aramid-S-methyl, fenoxam, indapoxam Azoxystrobin, fluopyram, isopropoxyfenozide, tetrazolium, pyridabenamide, pyridinesulfuronamide, fluoxadixyl, isopropoxyfenozide, carbendazim, cyclopyridamole, prochloraz, calcium cyclopyridamole, trifluoropyridinesulfuron, calcium phosphite, cis-jasmone, anti-rot ester, glyphosate, 2,4-dichlorophenoxyacetic acid, thiamethoxam, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4- Methyl triazol-1-yl)propionate, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate, methyl (Z)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoate, methyl (E)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoate (this compound can be prepared by the method described in JP 2023078251); methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (this compound can be prepared by WO Prepared by the method described in 2020 / 193387); (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; (5S)-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; 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 (these compounds can be prepared by WO Prepared by the method described in WO 2020 / 127780 and WO 2021 / 255070).2-[(2,6-difluoro-4-pyridinyl)-(tetrahydropyran-4-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide, 2-[(2,6-difluoro-4-pyridinyl)-(oxetane-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide, 2-[acetyl-(2,6-difluoro-4-pyridinyl)amino]-N -(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide, 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-5-methyl-N-spiro[3,4]oct-3-yl]-thiazol-4-carboxamide, 2-[(2,6-difluoro-4-pyridyl)-(2-methylpropionyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide (these compounds can be derived from WO4) Prepared by the methods described in 2017207362 A1, WO2019105933 A1, WO 2020109511 A1, WO 2021244952 A1; or Melaleuca alternifolia leaf oil (an extract of the tea plant Melaleuca alternifolia (commercially available as Timorx Gold®, a broad-spectrum plant-derived biofungicide)), or its salts, enantiomers, tautomers, or N-oxides, wherein components (B) and (C) are not the same compound, for the control or prevention of plant pathogenic microorganisms; Corynebacterium multiflorum Infection. Preferably, the plant is selected from cotton, corn, or soybean. In one embodiment, the plant is a genetically modified plant, preferably a Bt plant, more preferably a Bt soybean plant, Bt cotton, or Bt corn.

[0076] Component (C) compounds are referred to herein and above by their so-called "ISO common name" or another "common name" or trademark name, as used in individual cases. Component (C) compounds are known and commercially available and / or can be prepared using procedures known in the art.

[0077] In another embodiment of the invention, a fungicidal composition is provided comprising a mixture of component (A) and components (B) and (C) as active ingredients, wherein component (A) is selected from compounds having formula (I), (IA), or (IB), and components (B) and (C) are selected from compounds including: benzo[a]fluopyram, fluopyram, fluopyram, pyraclostrobin, fluopyram, pyraclostrobin, fluopyram, bifenthionil, difenoconazole, cyclophosphamide, tebuconazole, hexaconazole, prothioconazole, propiconazole, fluopyram, tebuconazole, tetraflufenazole, fluopyram, fenbendazole, chlorfluazuron, sphagnumazol, paclobutrazol, azoxystrobin, oxadiazon, and difenoconazole. Azoxystrobin, azoxystrobin, metalaxyl-M, benzyl sulfide, butyl morpholine, pyraclostrobin, spirocyclam, mancozeb, chlorothalonil, captan, copper oxychloride, copper hydroxide, sulfur, fluoxadixyl acetamiprid, isopropylquinoline, fluopyram, dimethomorph, fluazinam, fluazinam, fosetyl-aluminum, aramid-S-methyl, tebufenozide, indapoxetine, fluopyram, isopropylfluopyram, tetrazolium Pyridine amide, pyridine oxadixyl, fluoxadixyl, isoprothiolane, iprodione, carbendazim, cyclophosphamide, prochloraz, calcium cyclophosphamide, trifluoropyridine amide, calcium phosphite, cis-jasmone, anti-rot ester, glyphosate, 2,4-dichlorophenoxyacetic acid, thiamethoxam, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate, 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate, (Z)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoic acid methyl ester, (E)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoic acid methyl ester (this compound can be derived from JP) (The compound can be prepared by the method described in WO 2020 / 193387); (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (this compound can be prepared by the method described in WO 2020 / 193387); (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; (5S)-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;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 (these compounds can be prepared by the methods described in WO2020 / 127780 and WO 2021 / 255070); 2-[(2,6-difluoro-4-pyridinyl)-(tetrahydropyran-4-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide, 2-[(2,6-difluoro-4-pyridinyl)-(oxetane-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide, 2-[acetyl-(2,6-difluoro- [4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide, 2-[acetyl-(2,6-difluoro-4-pyridinyl)amino]-5-methyl-N-spiro[3,4]oct-3-yl]-thiazol-4-carboxamide, 2-[(2,6-difluoro-4-pyridinyl)-(2-methylpropionyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide (these compounds can be derived from WO4) Prepared by the methods described in 2017207362 A1, WO 2019105933 A1, WO 2020109511 A1, WO2021244952 A1; or Melaleuca alternifolia leaf oil (an extract of the tea plant Melaleuca alternifolia (commercially available as Timorx Gold®, a broad-spectrum plant-derived biofungicide)), or its salts, enantiomers, tautomers, or N-oxides, wherein components (B) and (C) are not the same compound, for the control or prevention of plant pathogenic microorganisms; Corynebacterium multiflorum Infection. Preferably, the plant is selected from cotton, corn, or soybean. In one embodiment, the plant is a genetically modified plant, preferably a Bt plant, more preferably a Bt soybean plant, Bt cotton, or Bt corn.

[0078] In a preferred composition according to this aspect of the invention, component (A) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide (compound IA), or a salt, enantiomer, tautomer, or N-oxide thereof, and components (B) and (C) are compounds selected from: benzo[a]fluorobenzoate, fluopyram, fluopyram, pyraclostrobin, pyraclostrobin, pyraclostrobin, fluopyram, bifenthionil, difenoconazole, cycloconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, fluopyram, tebuconazole, tetraflufenazole, fluopyram, fenbendazole, chlorfluazuron, styraclostrobin, paclobutrazol, azoxystrobin, oxadiazon, pyridaben. Azoxystrobin, azoxystrobin, metalaxyl-M, benzyl sulfide, butyl morpholine, pyraclostrobin, spirocyclam, mancozeb, chlorothalonil, captan, copper oxychloride, copper hydroxide, sulfur, fluoxadixyl acetamiprid, isopropylquinoline, fluopyram, dimethomorph, fluazinam, fluazinam, fosetyl-aluminum, aramid-S-methyl, tebufenozide, indapoxetine, fluopyram, isopropylfluopyram, tetrazolium Pyridine amide, pyridine oxadixyl, fluoxadixyl, isoprothiolane, iprodione, carbendazim, cyclophosphamide, prochloraz, calcium cyclophosphamide, trifluoropyridine amide, calcium phosphite, cis-jasmone, anti-rot ester, glyphosate, 2,4-dichlorophenoxyacetic acid, thiamethoxam, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate, 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate, (Z)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoic acid methyl ester, (E)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoic acid methyl ester (this compound can be derived from JP) (The compound can be prepared by the method described in WO 2020 / 193387); (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (this compound can be prepared by the method described in WO 2020 / 193387); (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; (5S)-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;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 (these compounds can be prepared by the methods described in WO 2020 / 127780 and WO 2021 / 255070); 2-[(2,6-difluoro-4-pyridinyl)-(tetrahydropyran-4-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide, 2-[(2,6-difluoro-4-pyridinyl)-(oxetane-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide, 2-[acetyl-(2,6-difluoro- [4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide, 2-[acetyl-(2,6-difluoro-4-pyridinyl)amino]-5-methyl-N-spiro[3,4]oct-3-yl]-thiazol-4-carboxamide, 2-[(2,6-difluoro-4-pyridinyl)-(2-methylpropionyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide (these compounds can be derived from WO4) Prepared by the methods described in 2017207362 A1, WO 2019105933 A1, WO 2020109511 A1, WO 2021244952A1; or Melaleuca alternifolia leaf oil (an extract of the tea plant Melaleuca alternifolia (commercially available as Timorx Gold®, a broad-spectrum plant-derived biofungicide)), or its salts, enantiomers, tautomers, or N-oxides, wherein components (B) and (C) are not the same compound, for the control or prevention of plant pathogenic microorganisms; Corynebacterium multiflorum Infection. Preferably, the plant is selected from cotton, corn, or soybean. In one embodiment, the plant is a genetically modified plant, preferably a Bt plant, more preferably a Bt soybean plant, Bt cotton, or Bt corn.

[0079] In another preferred composition according to this aspect of the invention, component (A) is N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acrylamide (compound IB), or a salt, enantiomer, tautomer, or N-oxide thereof, and components (B) and (C) are compounds selected from: benzo[a]fluorobenzoate, fluopyram, fluopyram, pyraclostrobin, fluopyram, pyraclostrobin, fluopyram, bifenthionil, difenoconazole, cycloconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, fluopyram, tebuconazole, tetraflufenazole, fluopyram, fenbendazole, chlorfluazuron, styraclostrobin, paclobutrazol, azoxystrobin, oxadiazon, pyridaben. Azoxystrobin, azoxystrobin, metalaxyl-M, benzyl sulfide, butyl morpholine, pyraclostrobin, spirocyclam, mancozeb, chlorothalonil, captan, copper oxychloride, copper hydroxide, sulfur, fluoxadixyl acetamiprid, isopropylquinoline, fluopyram, dimethomorph, fluazinam, fluazinam, fosetyl-aluminum, aramid-S-methyl, tebufenozide, indapoxetine, fluopyram, isopropylfluopyram, tetrazolium Pyridine amide, pyridine oxadixyl, fluoxadixyl, isoprothiolane, iprodione, carbendazim, cyclophosphamide, prochloraz, calcium cyclophosphamide, trifluoropyridine amide, calcium phosphite, cis-jasmone, anti-rot ester, glyphosate, 2,4-dichlorophenoxyacetic acid, thiamethoxam, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate, 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate, (Z)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoic acid methyl ester, (E)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoic acid methyl ester (this compound can be derived from JP) (The compound can be prepared by the method described in WO 2020 / 193387); (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (this compound can be prepared by the method described in WO 2020 / 193387); (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; (5S)-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;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 (these compounds can be prepared by the methods described in WO2020 / 127780 and WO 2021 / 255070); 2-[(2,6-difluoro-4-pyridinyl)-(tetrahydropyran-4-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide, 2-[(2,6-difluoro-4-pyridinyl)-(oxetane-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide, 2-[acetyl-(2,6-difluoro- [4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide, 2-[acetyl-(2,6-difluoro-4-pyridinyl)amino]-5-methyl-N-spiro[3,4]oct-3-yl]-thiazol-4-carboxamide, 2-[(2,6-difluoro-4-pyridinyl)-(2-methylpropionyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide (these compounds can be derived from WO4) Prepared by the methods described in 2017207362 A1, WO 2019105933 A1, WO 2020109511 A1, WO2021244952 A1; or Melaleuca alternifolia leaf oil (an extract of the tea plant Melaleuca alternifolia (commercially available as Timorx Gold®, a broad-spectrum plant-derived biofungicide)), or its salts, enantiomers, tautomers, or N-oxides, wherein components (B) and (C) are not the same compound, for the control or prevention of plant pathogenic microorganisms; Corynebacterium multiflorum Infection. Preferably, the plant is selected from cotton, corn, or soybean. In one embodiment, the plant is a genetically modified plant, preferably a Bt plant, more preferably a Bt soybean plant, Bt cotton, or Bt corn.

[0080] Combining components (B) and (C) with component (A) can enhance the latter's antifungal efficacy, and vice versa. Additionally, antifungal compositions can be effective against a broader spectrum of fungal pathogens, and these compositions, when used alone, can target individual active ingredients. Typically, the weight ratio of component (A) to the mixture of components (B) and (C) can be 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 to 1:5. Otherwise, the weight ratio of component (A) to the mixture of components (B) and (C) can be 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. These mixing ratios should be understood to include both weight-based ratios and molar ratios.

[0081] In embodiments of the present invention, the composition comprises component (A), component (B), and component (C), wherein the weight ratio of component (A) to the sum of components (B) and (C) may be 100:1 to 1:100, preferably 50:1 to 1:50, more preferably 20:1 to 1:40, even more preferably 15:1 to 1:30, still more preferably 12:1 to 1:25, or 10:1 to 1:20, or 10:1 to 1:10, or 5:1 to 1:15, or 5:1 to 1:5, or 4:1 to 1:4, or 3:1 to 1:10, or 3:1 to 1:3, or 2:1 to 1:5, or 1:1.

[0082] These component (B) compounds are referred to in this document and above by the so-called "ISO common name" or another "common name" or trademark name used in individual cases. Component (B) compounds are known and commercially available and / or can be prepared using procedures known in the art and / or procedures reported in the literature, such as WO 2015 / 155075 and WO 2016 / 202742, WO 2017 / 005710, WO 2018 / 108977, WO 2018 / 153707, WO 2018 / 098216, WO2019 / 093522, WO 2018 / 145921, WO 2015 / 185485, WO 2017 / 076742, WO 2017 / 081311, WO2017 / 085100, WO 2017 / 093019, WO 2017 / 178245, and WO 2017 / 211649.

[0083] In embodiments of the invention, the composition comprises component A, wherein component A is selected from compounds having formula (I), (IA), or (IB), a first component (B), and a second component (B), wherein the second component (B) is different from the first component (B). The weight ratio of component (A) to the sum of the first component (B) and the second component (B) can be 100:1 to 1:100, preferably 50:1 to 1:50, more preferably 20:1 to 1:40, even more preferably 15:1 to 1:30, still more preferably 12:1 to 1:25, or 10:1 to 1:20, or 10:1 to 1:10, or 5:1 and 1:15, or 5:1 to 1:5, or 4:1 to 1:4, or 3:1 to 1:1:1. 10, or 3:1 to 1:3, or 2:1 to 1:5, or 1:1.

[0084] Throughout this document, the term "composition" refers to different mixtures or combinations of component A, wherein component A is selected from compounds having formula (I), (IA), or (IB), and component (B) (including the embodiments defined above), for example in a single "ready-to-use with water" form, as a combined spray mixture (which consists of separate formulations of these single active ingredient components) (e.g., a "tank mix"), and when applied in a sequential manner (i.e., one after another, such as hours or days), as a combination of these single active ingredients. The order in which component A (wherein component A is selected from compounds having formula (I), (IA), or (IB)) and component (B) are applied is not critical for carrying out the invention.

[0085] In one embodiment of the invention, a method for controlling harmful fungi is provided, wherein the harmful organism, its habitat, breeding ground, its location, or plants, soil, or plant propagation material (preferably seeds) to be protected from the harmful organism is treated with an effective amount of the compound of formula (I) according to the invention.

[0086] In one embodiment of the invention, a method for controlling harmful fungi is provided, wherein the harmful organism, its habitat, breeding ground, its location, or plants, soil, or plant propagation material (preferably seeds) to be protected from the harmful organism is treated with a composition containing an effective amount of a compound of formula (I) according to the invention.

[0087] Preferably, the compounds of the present invention and compositions comprising the compounds having formula (I) are suitable for controlling fungal plant diseases.

[0088] The compounds of the present invention are also important for controlling a variety of fungi on various cultivated plants, as well as on a variety of seeds, including: bananas, cotton, vegetable species such as cucumbers, legumes, and gourds; cereals such as corn, wheat, rye, barley, rice, and oats; grasses, coffee, potatoes, sweet potatoes, corn, fruit trees, soybeans, tobacco, tomatoes, grapevines, ornamental plants, and sugarcane. In preferred embodiments, the compounds of formula (I), (IA), or (IB) according to the present invention are used on soybeans, cotton, and corn. In preferred embodiments, the compounds of formula (I), (IA), or (IB) according to the present invention are used on genetically modified plants selected from soybeans, cotton, and corn. Preferably, the genetically modified plants selected from soybeans, cotton, and corn are Bt plants, such as Bt soybeans, Bt cotton, and Bt corn.

[0089] In one embodiment, compounds of formula (I), (IA), or (IB) according to the invention are particularly suitable for controlling the effects of... Alternaria species ( Alternaria spp (Alternaria leaf spot disease) Cercospora species ( Cercospora spp. (Cercospora leaf spot disease) Corynebacterium multiflorum (Leaf spot disease) cottonseed spores ( Ascochyta gossypii (Cotton leaf blight) is a cotton disease caused by cotton bollworm; by Fusarium oxysporum specialized type ( Fusarium oxysporum f. sp. ) caused cotton (upland cotton ( Gossypium hirsutum L.)) Fusarium wilt disease.

[0090] Preferably, compounds of formula (I), (IA), or (IB) according to the invention are particularly suitable for controlling the composition of... Multi-master corynebacterium The resulting cotton disease (leaf spot).

[0091] In one embodiment, the compound of formula (I), (IA), or (IB) according to the invention is suitable for controlling the following fungal diseases on soybeans: Alternaria species (Alternaria leaf spot); Cercospora species (Cercospora leaf spot), for example... Cercospora soybeani ( C. sojina )or Cercospora Kikuchi ( C. kikuchii ); genus Colletotrichum ( Colletotrichum (Sexual form: Microcystis species (anthrax), for example) Flathead anthrax bacteria ( C. truncatum )or Colloidal anthrax ( C. gloeosporioides ); Corynebacterium multiflorum (Leaf spot disease); White feather disease fungus ( Dematophora necatrix (Sexual form: *Carya spp.*) (Root rot and stem rot); *Cyclocarya* species, for example Intercalation of bean shells ( D. phaseolorum (Dampness-induced disease); Fusarium species (sexual form: Fusarium) (wilt, root rot, or stem rot), for example Fusarium tuldosum ( F. tucumaniae )and Fusarium brasiliensis (F) brasiliense Each of these factors can cause sudden death syndrome in soybeans; Coccidioides moniliforme ( Macrophomina phaseolina (Synonyms: Macropomina phaseoli) (root rot and stem rot); Diffusion forkshell ( Microsphaera diffusa )(powdery mildew); species of the genus *Peronospora* ( Peronospora spp (downy mildew), for example Soybean downy mildew ( P. manshurica ); Bean rust fungus ( Phakopsora pachyrhizi )and Bractopus spp. ( P. meibomiae (Soybean rust); species of the genus *Pyrhodotorula*, such as Soybean stem brown rot fungus ( P. gregata. stem rot ); species of the genus *Pseudomonas* ( Phomopsis spp For example, stem rot: Common bean stem spot ( P. phaseoli (Sexual type:) Intercalation of bean shells ); species of the genus Pythium ( Pythium spp (Sudden collapse); Phytophthora species ( Phytophthora spp (Fusarium wilt, root rot, leaf rot, fruit rot, and stem rot), for example Soybean Phytophthora ( P. megasperma (Synonyms) P. sojae ); Rhizoctonia species ( Rhizoctonia spp .),For example Rhizoctonia solani ( R. solani (Root rot and stem rot); Species of the genus Sclerotinia ( Sclerotinia spp. (Stem rot or white mold); Fibrocystis Species ( Septoria spp .),For example Soybean shell needle spores ( S. glycines (Brown spot disease); Neat small sclerotium ( S. rolfsii (Synonyms) Aspergillus roximatei ( Athelia rolfsii ));or species of the genus *Rhizophora* ( Thielaviopsis spp. (Black root rot).

[0092] Preferably, compounds of formula (I), (IA), or (IB) according to the invention are suitable for controlling the composition of... Multiple Masters Corynebacterium This causes soybean diseases (leaf spot).

[0093] Preferably, the compounds of the present invention, or fungicidal compositions of the present invention containing said compounds, can be used to control or prevent plant pathogenic diseases on soybean plants, especially plant pathogenic fungi (such as...). Corynebacterium multiflorum ).

[0094] In another embodiment of the invention, a method for controlling or preventing genetically modified plants from being affected by plant pathogenic fungi, particularly such as... Multi-master corynebacterium A method of infection, wherein a compound having formula (I) according to the invention is applied to the plant. Preferably, the genetically modified plant is selected from soybean, cotton, and corn. In another preferred embodiment, the genetically modified plant is a BT plant selected from Bt soybean, Bt cotton, and Bt corn. In another preferred embodiment, the genetically modified plant is a BT plant selected from Bt soybean and Bt cotton.

[0095] Examples of commercially available genetically modified soybean plants that can preferably be treated according to the present invention include, but are not limited to, commercially available products such as plant seeds Intacta®, Intacta®2, Intacta® Roundup Ready™ 2 Pro (Intacta®RR2 PRO), Intacta®2 Xtend™, Cultivance, Conkesta soybean, Conkesta EnlistE3™ soybean, Enlist™ soybean, Enlist E3™ soybean, Roundup Ready™ soybean, Roundup Ready™ 2Xtend™, Genuity® Roundup Ready™ 2 Xtend™, Genuity® Roundup Ready 2 Yield™, herbicide-tolerant soybean lines, Optimum GAT™, Liberty Link™ soybean, Vistive Gold™, Verdeca HB4 soybean, Treus™, and Plenish™.

[0096] In one embodiment of the present invention, a method for controlling or preventing genetically modified soybean plant vegetation, particularly plant pathogenic fungi, is provided, especially... Corynebacterium multiflorum A method of infection in which a compound having formula (I) according to the invention is applied to the soybean plant, wherein the soybean plant is BT soybean. Preferably, the BT soybean plant is selected from Intacta RR2 PRO® or Conkesta Enlist E3®.

[0097] In a preferred embodiment of the present invention, a method for controlling the growth of pollutants on soybean plants is provided. Corynebacterium multiflorum The method, wherein the soybean plant is a genetically modified soybean plant, preferably a Bt soybean plant, is characterized by comprising the steps of: contacting the plant, its parts, its propagation material, pests, their food sources, habitats or breeding grounds with a compound selected from: N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide according to structure IA; or

[0098] (IA)

[0099] Based on the structure IB, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acrylamide

[0100] (IB).

[0101] In a more preferred embodiment of the present invention, a method for controlling the growth of pollutants on soybean plants is provided. Corynebacterium multiflorum The method, wherein the soybean plant is a genetically modified soybean plant, preferably a Bt soybean plant, is characterized by comprising the step of contacting the plant, its parts, its reproductive material, pests, their food sources, habitats or breeding grounds with a compound having formula (IA).

[0102] In another preferred embodiment of the present invention, a method for controlling the growth of pollutants on soybean plants is provided. Multi-master spore bacteria The method, wherein the soybean plant is a genetically modified soybean plant, preferably a Bt soybean plant, is characterized by comprising the step of contacting the plant, its parts, its reproductive material, pests, their food sources, habitats or breeding grounds with a compound having formula (IB).

[0103] In another preferred embodiment of the invention, the compound of the invention or the fungicidal composition of the invention comprising the compound can be used to control or prevent plant pathogenic diseases on cotton plants, especially plant pathogenic fungi (such as...). Corynebacterium multiflorum ).

[0104] Examples of commercially available genetically modified cotton plants that can preferably be treated according to the present invention include, but are not limited to, commercially available products such as plant seeds Bolgard®, Bolgard II™ cotton, LibertyLink®, RoundupReady™, WideStrike™ cotton, Bolgard® III x Roundup Ready™ Flex™, GlyTol™, GlyTol™ Liberty Link™, Glytol™ x Twinlink™, GlyTol LibertyLink TwinLink®Plus, Fibermax™ Liberty Link™, Bolgard™ cotton, Ingard™, Roundup Ready™ Bolgard™ cotton, Roundup Ready™ Flex™ cotton, Roundup Ready™ Flex™ Bollgard II™ cotton, TwinLink™ cotton, and BXN™ cotton.

[0105] In one embodiment of the present invention, a method for controlling or preventing genetically modified cotton plants from being affected by plant pathogenic fungi, particularly such as... Corynebacterium multiflorumA method of infection, wherein a compound having formula (I) according to the invention is applied to the cotton plant, and wherein the cotton plant is Bt cotton. Preferably, the Bt cotton plant is selected from WideStrike™ cotton, Bollgard® III x Roundup Ready™ Flex™, GlyTol™ LibertyLink™, GlyTol LibertyLink TwinLink® Plus, Bollgard II™ cotton, Bollgard™ cotton Ingard™, Roundup Ready™ Bollgard™ cotton, Roundup Ready™ Flex™ cotton, and TwinLink™ cotton.

[0106] In a preferred embodiment of the present invention, a method for controlling the growth of pollutants on cotton plants is provided. Corynebacterium multiflorum The method, wherein the cotton plant is a genetically modified cotton plant, preferably a Bt cotton plant, is characterized by comprising the steps of: contacting the plant, its parts, its propagation material, pests, their food sources, habitats or breeding grounds with a compound selected from: N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide according to structure IA; or

[0107] (IA)

[0108] Based on the structure IB, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acrylamide

[0109] (IB).

[0110] In a more preferred embodiment of the present invention, a method for controlling the growth of pollutants on cotton plants is provided. Corynebacterium multiflorum The method, wherein the cotton plant is a genetically modified cotton plant, preferably a Bt cotton plant, is characterized by comprising the step of contacting the plant, its parts, its reproductive material, pests, their food sources, habitats or breeding grounds with a compound having formula (IA).

[0111] In another preferred embodiment of the invention, a method for controlling the growth of pollutants on cotton plants is provided. Multi-master spore bacteriaThe method, wherein the cotton plant is a genetically modified cotton plant, preferably a Bt cotton plant, is characterized by comprising the step of contacting the plant, its parts, its reproductive material, pests, their food sources, habitats or breeding grounds with a compound having formula (IB).

[0112] Compounds having formula (I), (IA), or (IB) according to the present invention, or fungicidal compositions comprising said compounds according to the present invention, can be used to control or prevent plant pathogenic diseases on soybean plants, especially plant pathogenic fungi such as... Corynebacterium multiflorum .

[0113] In one embodiment, a compound of formula (I), (IA), or (IB) according to the invention, or a fungicidal composition comprising said compound according to the invention, can be used to control or prevent plant pathogenic diseases on genetically modified soybean plants, preferably Bt soybean plants, especially plant pathogenic fungi such as… Corynebacterium multiflorum .

[0114] Compounds having formula (I), (IA), or (IB) according to the present invention, or fungicidal compositions comprising said compounds according to the present invention, can be used to control or prevent plant pathogenic diseases on cotton plants, especially plant pathogenic fungi such as... Corynebacterium multiflorum .

[0115] Compounds having formula (I), (IA), or (IB) according to the present invention, or fungicidal compositions comprising said compounds according to the present invention, can be used to control or prevent plant pathogenic diseases on genetically modified cotton plants, preferably Bt cotton plants, especially plant pathogenic fungi such as… Corynebacterium multiflorum .

[0116] In certain circumstances, fungicidal compositions according to the invention comprising compounds having formula (I), (IA), or (IB) are used to control or prevent plant pathogenic diseases, particularly plant pathogenic fungi (such as...) on plants selected from soybean and cotton (especially any genetically modified plants as described above). Corynebacterium multiflorum When ), synergistic interactions between active ingredients can be observed.

[0117] Specifically, transgenic soybean plants expressing toxins such as insecticidal proteins like delta-endotoxins (e.g., Cry1Ac (Cry1Ac Bt protein)). Therefore, this can include transgenic soybean plants comprising: event MON87701 (disclosed in WO2009 / 064652), event MON87701 × MON89788 (disclosed in WO 2014 / 170327, e.g., as Intacta RR2 PRO). ® Soybeans available for commercial purchase), Event MON87751 (disclosed in WO 2014 / 201235), Event DAS-44406-6 (e.g., as Enlist E3) TM Commercially available, DAS-44406-6, disclosed in WO 2012 / 075426, or event DAS-81419-2 (described in WO 2013 / 016527, for example, as Conkesta) TM Soybeans are commercially available); Event DAS-81419-2 × DAS-44406-6 (e.g., as Conkesta™ Enlist E3™ soybeans are commercially available).

[0118] Useful transgenic events in transgenic soybean plants that can be treated according to the present invention include event DAS-44406-6 / pDAB8264.44.06.1 (soybean, herbicide tolerance, disclosed in WO 2012 / 075426); event DAS-81419-2 (described in WO 2013 / 016527, for example, as aka Conkesta). TM Commercially available soybeans, including Conkesta™ EnlistE3™ soybeans, DAS-81419-2 × DAS-44406-6; Event DAS-14536-7 / pDAB8291.45.36.2 (soybeans, herbicide tolerance, disclosed in WO 2012 / 075429); DAS-68416-4 (soybeans, herbicide tolerance, ATCC Registry No. PTA-10442, disclosed in WO 2011 / 066384, WO 2011 / 066360); Event DP-305423-1 (soybeans, quality mark, disclosed in WO 2008 / 054747, e.g., as Treus) TM Plenish TMPlenish® High Oleic Soybeans are commercially available; Event DP-356043-5 (Soybean, herbicide tolerance, deposited as ATCC PTA-8287, disclosed in WO2008 / 002872, for example as Optimum GAT™ commercially available); Event FG72 (Soybean, herbicide tolerance, disclosed in WO 2011 / 063413); Event LL27 (Soybean, herbicide tolerance, disclosed in WO 2006 / 108674); Event LL55 (Soybean, herbicide tolerance, disclosed in WO 2006 / 108675); Event EE-GM3 / FG72 (Soybean, herbicide tolerance), optionally superimposed with Event EE-GM1 / LL27 or Event EE-GM2 / LL55 (disclosed in WO 2011 / 063413); Event MON87701 (Soybean, insect control, disclosed in WO 2009 / 064652, WO 2014 / 170327); Event MON87701 × MON89788 (disclosed in WO 2014 / 170327, for example as Intacta RR2 PRO) ®Commercially available soybeans); Event MON87705 (soybean, improved fatty acid profile, herbicide tolerance, disclosed in WO 2010 / 037016 or US20100080887 A, commercially available, e.g., as Visive Gold™); Event MON87751 (lepidopteran resistance, ATCC Registry No. PTA-120166, disclosed in WO 2014 / 201235); Event MON87751 × MON87701 × MON89788 × MON87708 (commercially available, as Intacta2 Xtend®); Event MON87708 (soybean, herbicide tolerance, disclosed in WO 2011 / 034704, commercially available, e.g., as Genuity® Roundup Ready™ 2 Xtend™); Event MON87708 × MON89788 (soybean, e.g., as Roundup Ready™ 2). Xtend™ is commercially available); Event MON87712 (Soybean, yield, disclosed in WO 2012 / 051199); Event MON87754 (Soybean, quality characteristics, disclosed in WO 2010 / 024976); Event MON87769 (Soybean, quality attributes, disclosed in WO 2009 / 102873); Event MON89788 (Soybean, herbicide tolerance, disclosed in WO 2006 / 130436, for example as commercially available as Genuity® RoundupReady 2 Yield™); Event SYHT0H2 / SYN-000H2-5 (Soybean, herbicide tolerance, disclosed in WO 2012 / 082548); Event DAS-21606-3 (Soybean, herbicide tolerance, disclosed in WO 2012 / 082548). Event 8264.44.06.1 (Soybean, superimposed herbicide tolerance, disclosed in WO 2022 / 012075426); Event pDAB8291.45.36.2 (Soybean, superimposed herbicide tolerance, disclosed in WO 2012 / 075429); Event pDAB8264.42.32.1 (Soybean, superimposed herbicide tolerance, disclosed in WO 2013 / 010094); Event A2704-12 (Glufosinate tolerance, disclosed in WO 2006 / 108647); Event A5547-127 (Syringin tolerance, disclosed in WO2006 / 108675); Event BPS-CV127-91 (Herbicide tolerance, disclosed in WO 2010 / 080829); Event GU262 (Syringin tolerance, described in APHIS regulatory reference US 98-238-01p); Event MON 87708 × MON89788 × A5547-127; G72 × A5547-127 (Event code: MST-FGØ72-3 × ACS-GMØØ6-4, e.g., as Liberty Link). TM Soybeans are commercially available), 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., as RoundupReady® soybeans are commercially available), Event HB4 (Event code IND-00410-5, US 2022 / 009011, e.g., as Verdeca HB4 soybeans are commercially available).

[0119] Transgenic events that may be particularly useful in transgenic soybean plants treated according to the present invention include event A2704-12 (glufosinate tolerance, disclosed in WO 2006 / 108647, for example, as Liberty Link). TM Soybeans are commercially available), Event A5547-127 (phosphinic acid resistant, disclosed in WO 2006 / 108675, US 8952142 B2, for example, as Liberty Link) TM Commercially available soybeans); A5547-35 (Event code: ACS-GMØØ8-6, gene: pat, e.g., commercially available as Liberty Link™ soybeans); Event MON89788 (soybean, herbicide tolerance, disclosed in WO 2006 / 130436, e.g., commercially available as Genuity® Roundup Ready 2 Yield™); DP-305423-1 (soybean, quality mark, disclosed in WO 2008 / 054747, e.g., as Treus TM Plenish TMPlenish® high oleic soybeans are commercially available; Event MON87701 (soybean, insect resistance, disclosed in WO 2009 / 064652); Event MON87701 × MON89788 (disclosed in WO 2014 / 170327, e.g., as Intacta RR2 PRO). ® Commercially available soybeans); Event MON87705 (soybeans, improved fatty acid profile, herbicide tolerance, disclosed in WO 2010 / 037016 or US20100080887 A, e.g., commercially available as Visive Gold™); Event FG72 (soybeans, herbicide tolerance, disclosed in WO 2011 / 063413); Event FG72 × A5547-127 (e.g., as LibertyLink® GT27) TM Commercially available); Event SYHT0H2 / SYN-000H2-5 (soybean, herbicide tolerance, disclosed in WO 2012 / 082548); Event DAS-81419-2 (described in WO 2013 / 016527, e.g., as Conkesta) TM Soybeans are commercially available); Event DAS-44406-6 (disclosed in WO 2012 / 075426, e.g., as Enlist E3) TM (commercially available), or event DAS-81419-2 (described in WO 2013 / 016527, for example, as Conkesta) TM Soybeans available for commercial sale); DAS81419-2 × DAS4406 (e.g., available for commercial sale as Conkesta™ Enlist E3™ soybean); Event DP305423 × GTS 40-3-2 (soybeans, quality mark, disclosed in WO 2008 / 054747, e.g., available for commercial sale as Plenish® high oleic soybean); Event DP-356043-5 (soybeans, herbicide tolerance, preserved as ATCC PTA-8287, disclosed in WO 2008 / 002872, e.g., available for commercial sale 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 (For example, commercially available as RoundupReady® soybeans).

[0120] In addition, this list of genetically modified events is provided by the U.S. Department of Agriculture's (USDA) Animal and Plant Health Inspection Service (APHIS) and can be found on its World Wide Web website at aphis.usda.gov.

[0121] Transgenic soybeans containing herbicide tolerance genes include, 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, SYHTØH2, W62, W98, FG72, and CV127.

[0122] According to one embodiment of the invention, the use of compounds having formula (I), (IA), or (IB) for controlling plant pathogenic fungi in genetically modified soybean plants, wherein the transgenic soybean containing a herbicide tolerance gene is, 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, SYHTØH2, W62, W98, FG72, and CV127 is provided.

[0123] Transgenic cotton events containing herbicide tolerance genes include, for example (but excluding others), 19-51 a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN1021 1, BXN 10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB1 19, GHB614, LLCotton25, T303-3, and T304-40.

[0124] Transgenic cotton events containing insecticidal protein genes include, for example (but not excluding others), SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB1 19, and SGK321. Increased ear biomass has been achieved by using the transgenic athb17 present in the maize event MON87403, or by using the transgenic bbx32 present in the soybean event MON87712 to enhance photosynthesis.

[0125] Transgenic cotton events containing the glufosinate tolerance gene include, for example (but not excluding others): 3006-210-23 × 281-24-236 × MON 1445 (event code: DAS-21023-5 × DAS-24236-5 × MON-01445-2, gene: bar, e.g., commercially available as WideStrike™ Roundup Ready™ cotton), 3006-210-23 ×281-24-236 × MON88913 (event code: DAS-21023-5 × DAS-24236-5 × MON-88913-8, gene: bar, e.g., commercially available as Widestrike™ Roundup Ready Flex™ cotton), 3006-210-23 ×281-24-236 × MON88913 × COT102 (Event Code: DAS-21023-5 × DAS-24236-5 × MON-88913-8 × SYN-IR102-7, Gene: pat, e.g., commercially available as Widestrike™ × Roundup Ready Flex™ × VIPCOT™ cotton), GHB614 × LLCotton25 (Event Code: BCS-GH002-5 × ACS-GH001-3, Gene: bar, e.g., commercially available as GlyTol™ Liberty Link™), GHB614 × T304-40 × GHB119 (Event Code: BCS-GH002-5 × BCS-GH004-7 × BCS-GH005-8, Gene: bar, e.g., as Glytol™ × Twinlink™ (commercially available), LLCotton25 (event code: ACS-GH001-3, gene: bar, e.g., commercially available as ACS-GH001-3), GHB614 × T304-40 × GHB119 × COT102 (event code: BCS-GH002-5 × BCS-GH004-7 × BCS-GH005-8 × SYN-IR102-7, gene: bar, e.g., commercially available as Glytol™ × Twinlink™ × VIPCOT™ cotton), LLCotton25 × MON 15985 (event code: ACS-GH001-3 × MON-15985-7, gene: bar, e.g.,Commercially available as Fibermax™ Liberty Link™ Bollgard II™, T304-40 × GHB1 19 (Event code: BCS-GH004-7 × BCS-GH005-8, gene: bar, e.g., commercially available as TwinLink™ cotton), GHB614 × T304-40 × GHB1 19 × COT102 (Event code: BCS-GH002-5 × BCS-GH004-7 × BCS-GH005-8 × SYN-IR102-7, gene: bar, e.g., commercially available as Glytol™ × Twinlink™ × VIPCOT™ cotton), GHB1 19 (Event code: BCS-GH005-8, gene: bar), GHB614 × LLCotton25 × MON15985 (Event code: CS-GH002-5 × ACS-GH001-3 × MON-15985-7 (event code: MON88701, 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 × MON88913 (event code: MON 88701-3 × MON-88913-8, gene: bar), MON88701 × MON88913 × MON15985 (event code: MON 88701-3 × MON-88913-8 × MON-15985-7, gene: bar), 281-24-236 × 3006-210-23 × COT102 × 81910 (event code: DAS-24236-5 × DAS-21023-5 × SYN-IR102-7 × DAS-81910-7, gene: pat), COT102 × MON15985 × MON88913 × MON88701 (event code: SYN-IR102-7 × MON-15985-7 × MON-88913-8 × MON 88701-3,Gene: bar) and 3006-210-23 × 281-24-236 × MON88913 × COT102 × 81910 (Event code: DAS-21023-5 × DAS-24236-5 × MON-88913-8 × SYN-IR102-7 × DAS-81910-7, gene: pat).

[0126] In a preferred aspect of the invention, control or prevention of plant pathogenic microorganisms on plants is provided. Corynebacterium multiflorum A method of infection comprising applying a compound of formula (I), (IA) or (IB) to a plant pathogen, a site of the plant pathogen, or a plant susceptible to the plant pathogen, or its propagation material, wherein the compound of formula (I), (IA) or (IB) is applied in the field.

[0127] As used herein, the terms “field application,” “field growing,” and “field cultivation” broadly refer to the direct application of a pest-killing compound or composition to plants grown in a field or conventional agricultural environment, while “liquid culture application” typically involves the use of pest-killing compounds and compositions in a controlled, hydroponic, or soilless environment, where plants are grown in a nutrient-rich aqueous solution, such as for scientific research purposes. As previously indicated, compounds and compositions as defined herein have unexpectedly proven to be particularly effective for field application compared to liquid culture application.

[0128] In a preferred embodiment, the compound according to formula (I), (IA) or (IB) of the present invention is applied to field-grown plants susceptible to plant pathogens by foliar application, soil application, furrow application or drenching application.

[0129] In another embodiment, for the purpose of field cultivation of plants susceptible to plant pathogens, a compound according to formula (I), (IA) or (IB) of the present invention is applied to plant propagation material.

[0130] The compounds having formulas (IA) and (IB) according to the present invention can be prepared as shown in the following scheme (Scheme 1).

[0131] A compound having formula (I) can be produced by a compound having formula (II) (where R... 1 Selected from cyclopropyl or 1-methoxyethyl, R 2 It is a methoxy group, R 3 R 4 It is hydrogen and R 5(trifluoromethyl) is prepared by reacting with a compound having formula (III) or a compound having formula (IV), optionally in the presence of a, in a suitable solvent, at a temperature between 0°C and 75°C. For relevant examples, see WO 2003 / 028729, WO 2017 / 055473, and WO 2010 / 045251. This reaction is shown in Scheme 1.

[0132]

[0133] Option 1

[0134] For the purposes of this invention, compounds having formula (II) may be used in any tautomer form having different (E) / (Z) configurations.

[0135] Examples of compounds having formula (III) suitable for use in the methods of the present invention include those wherein R 1 Selected from those of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, and isobutyl. Preferably, R in compounds having formula (III) 1 It is methyl or ethyl. More preferably, compounds having formula (III) are methyl 2,2,2-trifluoroacetate or ethyl 2,2,2-trifluoroacetate.

[0136] Alternatively, examples of compounds having formula (III) suitable for use in the methods of the present invention include those wherein R 1 Selected from those of hydrogen or alkyl-C(=O)-alkyl. Examples of compounds having formula (III) suitable for use in the methods of the present invention include trifluoroacetic acid, trifluoroacetic acid esters, and trifluoroacetic anhydride.

[0137] Examples of compounds having formula (IV) suitable for use in the methods of the present invention include those wherein the halogen is selected from chlorine, bromine, or fluorine. Compounds having formula (IV) are preferably trifluoroacetyl chloride.

[0138] In embodiments of the method of the present invention, the compound having formula (I) is advantageously prepared by reacting the compound having formula (II) with 1.0 to 2.0 equivalent amounts of the compound having formula (III).

[0139] In a preferred embodiment of the invention, the method is carried out in the presence of at least one base.

[0140] According to one embodiment, the method of the present invention is carried out in the presence of at least one base and optionally at least one solvent.

[0141] Examples of suitable bases include inorganic and organic bases. Preferred bases are selected from the group consisting of: tertiary amines, substituted or unsubstituted pyridines, bicyclic amines and mixtures thereof, NaH, alkali metal hydroxides, alkali metal C1-6 alkoxylates and alkaline earth metal C1-6 alkoxylates, such as sodium methoxide, sodium hydroxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, potassium pentanoxide, potassium carbonate (K2CO3), sodium carbonate (Na2CO3), sodium bicarbonate (NaHCO3), triethylamine (TEA), and 3,5-dimethylpyridine or 2,6-dimethylpyridine.

[0142] As used herein, the term "alkali metal" refers to an element in Group 1 of the periodic table, preferably lithium (Li), sodium (Na), or potassium (K).

[0143] As used herein, the term "alkaline earth metals" refers to elements in Group 2 of the periodic table, preferably magnesium (Mg) or calcium (Ca).

[0144] Examples of suitable solvents include, for example, aromatic solvents (such as toluene, xylene, and dichlorobenzene), polar solvents (such as tetrahydrofuran (THF) and dimethyl carbonate (DMC)), or nonpolar solvents (such as methylcyclohexane (MCH)).

[0145] Other examples of solvents include, but are not limited to, methanol, ethanol, tert-butanol, 2-methyltetrahydrofuran, N,N - Dimethylformamide, dimethyl sulfoxide, pyridine, pyrrolidine, N-methyl-2-pyrrolidone, toluene, and dioxane.

[0146] The method of the present invention is generally carried out at a temperature between 0°C and 60°C, preferably between 0°C and 40°C, more preferably between 0°C and 25°C, or even more preferably between 25°C and 40°C. Very good results are obtained when the method of the present invention is carried out at a temperature between 0°C and 25°C or between 25°C and 40°C.

[0147] The method of the present invention is typically carried out at pressures of 1 atm to 5 atm (standard atmospheric pressure, abbreviated as atm, is a pressure unit equal to the average atmospheric pressure at sea level).

[0148] Typical reaction times are typically in the range of 1 to 16 hours. When the method of the present invention is carried out with a reaction time of 1 to 2 hours, very good results are obtained.

[0149] The method disclosed in Scheme 1 typically further includes the step of separating compounds having formula (I) using an aqueous medium. Compounds having formula (I) are advantageously separated from the reaction mixture using an aqueous medium, typically by post-extraction treatment.

[0150] In a preferred embodiment of the method of the present invention, the aqueous medium is an aqueous acidic medium. Aqueous acidic media are typically prepared by adding one or more acids to the aqueous medium. Preferably, the method of the present invention further includes the step of separating compounds having formula (I) using an aqueous acidic medium.

[0151] It has been found that an aqueous acidic medium during post-reaction treatment provides the most suitable medium for purifying compounds having formula (I). In particular, it has been unexpectedly found that the separation yield can be improved by adding an aqueous acidic medium to the reaction mixture.

[0152] Aqueous acidic media typically include acids selected from the group consisting of: acetic acid, citric acid, sulfuric acid, hydrochloric acid (HCl), HCl / water, and HCl / dioxane. Preferably, the aqueous acidic media include citric acid.

[0153] The aqueous acidic medium preferably has a pH of 2.0 to 6.0, more preferably 4.9.

[0154] Alternatively, compounds having formula (I) can be prepared from compounds having formula (II) by reacting them with trifluoroacetic acid, trifluoroacetic acid ester, trifluoroacetic anhydride, or trifluoroacetyl halide (including trifluoroacetyl fluoride, trifluoroacetyl chloride, and trifluoroacetyl bromide), optionally in the presence of a base (e.g., pyridine or 4-dimethylaminopyridine), in a suitable solvent (e.g., toluene, ethyl acetate, tetrahydrofuran, 2-methyltetrahydrofuran, or ethanol), at a temperature between 0°C and 75°C. For relevant examples, see WO 2003 / 028729, WO 2017 / 055473, and WO 2010 / 045251.

[0155] Methods for preparing compounds having formula (I) have been disclosed in WO 2018 / 177894 and WO 2020 / 212513. Methods for preparing compounds having formula (II) have been disclosed in WO 2018 / 177894 and WO 2020 / 212513.

[0156] Compounds having formula (II) (where R) 1 Selected from cyclopropyl or 1-methoxyethyl, it can be produced by compounds having formula (V) (where R... 1 Selected from cyclopropyl or 1-methoxyethyl, it is prepared by reacting with hydroxylamine hydrochloride or an aqueous solution of hydroxylamine in the presence of a base (such as triethylamine or potassium carbonate), in a suitable solvent (such as methanol or ethanol), at a temperature between 0°C and 80°C. In some cases, better reaction performance can be obtained by using a catalyst (e.g., 8-hydroxyquinoline). For relevant examples, see Kitamura, S. et al. Chem. Pharm. Bulletin. (2001), 49 , 268, WO 2017 / 055473 and WO 2013 / 066838. This reaction is shown in Scheme 2.

[0157]

[0158] Option 2

[0159] Compounds having formula (V) (where R) 1 Selected from cyclopropyl or 1-methoxyethyl) can be produced by compounds having formula (VI) (wherein R) 1 Selected from cyclopropyl or 1-methoxyethyl, wherein X is a suitable leaving group (e.g., Cl, Br, I, OH, or OSO2Me) via With amides or ureas having formula (XVII) in a base (e.g., triethylamine, N , N The reaction is carried out in the presence of diisopropylethylamine, K₂CO₃, NaHCO₃, or Na₂CO₃, in a suitable solvent (e.g., dimethylacetamide, tetrahydrofuran, 2-methyltetrahydrofuran, acetone, or acetonitrile), at a temperature between 0°C and 90°C. In some cases, better reaction performance can be obtained by using a catalyst (e.g., Bu₄NHSO₄, Bu₄NBr, Bu₄NI, NaI, or 4-dimethylaminopyridine) or optionally under microwave irradiation. For relevant examples, see Miyawaki, K. et al. Heterocycles [ Heterocyclic (2001), 54 , 887, WO 2003 / 028729 and WO 2013 / 066839. This reaction is shown in Scheme 3.

[0160]

[0161] Option 3

[0162] Compounds having formula (VII) (where R) 1 Selected from cyclopropyl or 1-methoxyethyl compounds, the compounds can be prepared via a coupling transformation of a compound having formula (IX) and a compound having formula (VIII) (where X is OH), the coupling transformation being performed by converting the -OH group (such as a chloride) to a leaving group prior to treatment with the compound having formula (IX), for example by using triphosgene, diphosgene, phosgene, (COCl)₂, or SOCl₂. The compounds having formula (VIII) are commercially available or prepared using known methods. For relevant examples, see Nelson, T. D, et al. Tetrahedron Lett. [ Tetrahedral fast Report [(2004), 45, 8917; Senthil, K. et al.] Pest. Res. Journal [ Journal of Pest Research ](2009), 21, 133; and Crich, D., Zou, Y. J. Org. Chem . [ Organic Chemistry Journal [(2005), 70,3309. This reaction is shown in scheme 4.]

[0163]

[0164] Option 4

[0165] Compounds of formula (I), (IA), or (IB) according to the invention can be used in their unmodified form, or preferably, together with adjuvants conventionally used in the field of formulations. For this purpose, they can be conveniently formulated in known manner as emulsifiable concentrates, coated pastes, directly sprayable or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, dusts, granules, and encapsulating agents, for example, in polymeric substances. The method of application, such as spraying, atomizing, dusting, spreading, coating, or watering, is selected according to the type of composition, the intended purpose, and the prevailing environment. The compositions may also contain additional adjuvants, such as stabilizers, defoamers, viscosity modifiers, binders or thickeners, and fertilizers, micronutrient donors, or other formulations for achieving specific effects.

[0166] Suitable carriers and adjuvants, for example for agricultural uses, can be solid or liquid and are useful in formulation techniques, such as natural or recycled minerals, solvents, dispersants, wetting agents, thickeners, binders, or fertilizers. Such carriers are described, for example, in WO 1997 / 33890.

[0167] Suspension concentrates are aqueous formulations in which finely dispersed solid particles of an active compound are suspended. Such formulations contain anti-settling agents and dispersants, and may further contain wetting agents to enhance activity, as well as antifoamers and crystal growth inhibitors. In use, these concentrates are diluted in water and are typically applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0168] Wettable powders are finely dispersed granular formulations that are easily dispersed in water or other liquid carriers. These granules contain active ingredients retained in a solid matrix. Typical solid matrices include bleaching clay, kaolin, silica, and other easily wettable organic or inorganic solids. Wettable powders typically contain 5% to 95% active ingredient plus small amounts of wetting agents, dispersants, or emulsifiers.

[0169] Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquids and may consist entirely of an active compound and a liquid or solid emulsifier, or may contain a liquid carrier such as xylene, heavy aromatic naphtha, isophorone, and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquids and are typically applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0170] Granular formulations consist of both extrudates and relatively coarse granules, and are typically applied undiluted to the area requiring treatment. Typical carriers used in granular formulations include sand, bleaching clay, attapulgite clay, bentonite, montmorillonite, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, crushed corn cobs, crushed peanut shells, sugar, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesium oxide, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate, and absorbent active compounds or other organic or inorganic materials that can be coated with active compounds. Granular formulations typically contain 5% to 25% of the active ingredient, which may include surfactants such as heavy aromatic naphtha, kerosene, and other petroleum fractions, or vegetable oils; and / or binders such as dextrin, gum, or synthetic resins.

[0171] Powders are free-flowing mixtures of active ingredients and finely dispersed solids such as talc, clay, flour, and other organic and inorganic solids that act as dispersants and carriers.

[0172] Active ingredients (compounds having formula (IA) or (IB) and mixtures thereof with component (B)) may also be contained in microcapsules. Microcapsules contain the active ingredient within a porous carrier. This allows the active ingredient to be released into the environment in a controlled amount (e.g., slowly). Microcapsules typically have a diameter of 0.1 to 500 micrometers. They contain approximately 25% to 95% by weight of the active ingredient. These active ingredients may be in the form of a monolithic solid, fine particles in a solid or liquid dispersion, or a suitable solution. The encapsulating membrane may comprise, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymers, polyacrylonitrile, polyacrylates, polyesters, polyamides, polyureas, polyurethanes, or chemically modified polymers, as well as starch xanthates, or other polymers known to those skilled in the art. Alternatively, very fine microcapsules may be formed in which the active ingredient is contained in a solid matrix of a base substance as finely dispersed particles, but these microcapsules themselves are not encapsulated.

[0173] Microcapsules are typically droplets or particles of active ingredient encapsulated in an inert porous shell, which allows the encapsulated material to escape into the environment at a controlled rate. The diameter of the encapsulated droplets is typically 1 to 50 micrometers. The encapsulated liquid typically constitutes 50% to 95% of the capsule weight and may contain a solvent in addition to the active compound. Encapsulated particles are typically porous particles, in which a porous membrane seals the pores, retaining the active species in liquid form within the pores. The diameter of the particles typically ranges from 1 millimeter to 1 centimeter, and preferably from 1 to 2 millimeters. The particles are formed by extrusion, aggregation, or spheroidization, or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust, and particulate carbon. Shell or membrane materials include natural and synthetic rubbers, cellulose materials, styrene-butadiene copolymers, polyacrylonitrile, polyacrylates, polyesters, polyamides, polyureas, polyurethanes, and starch xanthates.

[0174] Other useful formulations for agrochemical applications include simple solutions of the active ingredient in solvents such as acetone, alkylated naphthalene, xylene, and other organic solvents, in which the active ingredient is completely dissolved at the desired concentration. Pressurized sprays can also be used, in which the active ingredient is dispersed in a finely dispersed form due to the evaporation of the low-boiling-point dispersant solvent carrier.

[0175] Suitable agricultural adjuvants and carriers useful for formulating the compositions of the present invention among the above-described formulation types are well known to those skilled in the art.

[0176] Suitable liquid carriers include, for example, water, toluene, xylene, naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol rosin ester, 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, dipropylene glycol (diproxitol), alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, α-pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, γ-butyrolactone, glycerol, glyceryl diacetate, glyceryl monoethyl Ester, glyceryl triacetate, hexadecane, hexanediol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, cumene, isopropyl myristate, lactic acid, laurylamine, isopropyl acetone, methoxypropanol, methyl isopentyl ketone, methyl isobutyl ketone, methyl lauryl ketone, methyl octanoate, methyl oleate, dichloromethane, m-xylene, n-hexane, n-octylamine, stearic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol Ingredients include polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin wax, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol, and higher molecular weight alcohols (such as pentanol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc.), ethylene glycol, propylene glycol, glycerol, and N-methyl-2-pyrrolidone. Water is typically used as the carrier for diluting concentrates.

[0177] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, chalk, lime, calcium carbonate, bentonite, bleaching clay, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell powder, and lignin.

[0178] A wide range of surfactants are advantageously used in the liquid and solid compositions, especially those designed to be diluted with a carrier prior to application. These agents typically constitute 0.1% to 15% by weight of the formulation when used. They can be anionic, cationic, nonionic, or polymeric in nature and can be used as emulsifiers, wetting agents, suspending agents, or for other purposes. Typical surfactants include alkyl sulfates, such as diethanolammonium lauryl sulfate; alkyl aryl sulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol-epoxide addition products, such as nonylphenol-C.sub.18 ethoxylate; alcohol-epoxide addition products, such as tridecyl alcohol-C.sub.16 ethoxylate; soaps, such as sodium stearate; alkyl naphthalene sulfonates, such as sodium dibutylnaphthalene sulfonate; salts of dialkyl sulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary ammonium chloride, such as lauryltrimethylammonium 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 phosphates.

[0179] Other adjuvants commonly used in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, antifoaming agents, opacifiers, compatibility agents, antifoaming agents, multivalent chelating agents, neutralizing agents and buffers, corrosion inhibitors, dyes, flavor enhancers, spreading agents, penetration enhancers, micronutrients, softeners, lubricants, and fixatives.

[0180] Therefore, in embodiments, compounds of formula (I), (IA), or (IB) according to the present invention can be used in the form of a pest-killing composition, which further comprises one or more adjuvants selected from: stabilizers, viscosity regulators, adhesives, thickeners, fertilizers, crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, defoamers, opacifiers, compatibility agents, defoamers, multivalent chelating agents, neutralizers and buffers, corrosion inhibitors, dyes, flavor enhancers, spreading agents, penetration aids, micronutrients, softeners, lubricants, and fixatives.

[0181] The pest control composition may also contain one or more reagents that act as a carrier or diluent, or both, as the active ingredient. The reagent that acts as a carrier or diluent, or both (hereinafter referred to as "carrier or diluent"), may be liquid or solid.

[0182] In embodiments, compounds of formula (I), (IA), or (IB) according to the present invention can be used in the form of a pest-killing composition, which further comprises one or more liquid carriers or diluents selected from: xylene, heavy aromatic naphtha, isophorone, water, toluene, naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, Diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol rosinate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, dipropylene glycol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, α-pinene, d-limonene, ethylene glycol, ethyl... Diol butyl ether, ethylene glycol methyl ether, γ-butyrolactone, glycerol, glyceryl diacetate, glyceryl monoacetate, glyceryl triacetate, hexadecane, hexanediol, isoamyl acetate, isobornyl acetate, isooctane, cumene, isopropyl myristate, lactic acid, laurylamine, isopropyl acetone, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl lauryl ketone, methyl octanoate, methyl oleate, dichloromethane, m-xylene, n-hexane, n-octylamine, decadecyl... Octaic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol, higher molecular weight alcohols (pentanol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc.), and water (for diluting the concentrate).

[0183] In embodiments, compounds of formula (I), (IA), or (IB) according to the present invention can be used in the form of a pest-killing composition, which further comprises one or more solid diluents or carriers selected from: talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, chalk, diatomaceous earth, lime, calcium carbonate, bentonite, bleaching clay, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell powder, and lignin.

[0184] In embodiments, compounds of formula (I), (IA), or (IB) according to the present invention can be used in the form of a pest-killing composition, which further comprises one or more formulation adjuvants selected from unepoxidized or epoxidized vegetable oils, preservatives, and inorganic compounds.

[0185] Furthermore, other biocidal active ingredients or compositions may be combined with the compounds or compositions of the present invention and used in the methods of the present invention, and applied simultaneously or sequentially with the compounds or compositions of the present invention. When applied simultaneously, these additional active ingredients may be formulated or mixed together with the compounds or compositions of the present invention, for example, in a spray can. These additional biocidal active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides, and / or plant growth regulators.

[0186] The pesticides referred to in this article by their common names are, for example, known from "The Pesticide Manual", 15th edition, British Crop Protection Council 2009.

[0187] Additionally, the compositions of the present invention can be administered in combination with one or more systemically acquired resistance inducers (“SAR” inducers). SAR inducers are known and described, for example, in U.S. Patent No. 6,919,298, and include, for example, salicylates and the commercial SAR inducer aramid-benzene-S-methyl.

[0188] Compounds of formula (I), (IA), or (IB) according to the invention are generally used in the form of agricultural chemical compositions and can be applied simultaneously or sequentially with other compounds to the crop area or plants to be treated. For example, these other compounds may be fertilizers or micronutrient donors or other formulations that affect plant growth. They may also be selective or non-selective herbicides, and insecticides, fungicides, bactericides, nematicides, molluscicides, or mixtures of several of these formulations, if desired, together with other carriers, surfactants, or application-promoting adjuvants commonly used in the field of formulations.

[0189] Compounds of formula (I), (IA) or (IB) according to the invention can be used in the form of (fungicide) compositions for controlling or protecting against plant pathogenic microorganisms, which contain as active ingredients a compound in free form or in the form of a salt available for agricultural use as defined herein, and at least one of the above-described adjuvants, and preferably at least one formulation adjuvant, diluent and / or carrier.

[0190] Therefore, the present invention provides compositions comprising, preferably, fungicidal compositions, compounds having formula (I), (IA), or (IB) according to the invention, agriculturally acceptable carriers, and optionally adjuvants. Agriculturally acceptable carriers are, for example, carriers suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, in addition to compounds having formula (I), (IA), or (IB), the compositions may also contain at least one or more pest-killing compounds, such as additional fungicidal active ingredients.

[0191] The compound of formula (I), (IA), or (IB) according to the invention may be the sole active ingredient of the composition, or, where appropriate, it may be blended with one or more additional active ingredients, such as pest control agents, including fungicides, herbicides, insecticides, synergists, or plant growth regulators. In some cases, the additional active ingredients may produce unexpected synergistic activity.

[0192] Examples of suitable additional active ingredients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, aniline fungicides, antibiotic fungicides, aromatic fungicides, arsenic-containing fungicides, arylphenyl ketone fungicides, benzamide fungicides, benzoylaniline fungicides, benzimidazole fungicides, benzothiazole fungicides, plant-derived fungicides, bridging biphenyl fungicides, carbamate fungicides, phenyl carbamate fungicides, conazole fungicides, copper fungicides, diformimide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiopentane fungicides, furfural fungicides, furfurylamide fungicides, furfurylaniline fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides, and organophosphate fungicides. Organotin fungicides, oxathiin fungicides, oxazole fungicides, thiophene fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, acanthocyanin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides, and zinc fungicides.

[0193] Another aspect of the invention is a method for controlling diseases caused by plant pathogens on useful plants or their propagation material, the method comprising applying a composition according to the invention to the useful plants, their sites, or their propagation material. A preferred method comprises applying a composition according to the invention to the useful plants or their sites, more preferably to the useful plants. A further preferred method comprises applying a composition according to the invention to the propagation material of the useful plants.

[0194] Throughout this document, the term "composition" refers to various mixtures or combinations of components (A) and (B), for example, in a single "ready-to-use with water" form, as a combined spray mixture (consisting of individual formulations of these single active ingredient components) (e.g., a "tank mix"), and as a combination of these single active ingredients when applied sequentially (i.e., one after the other, such as hours or days). The order in which components (A) and (B) are applied is not important for carrying out this invention.

[0195] The compositions according to the invention are effective against harmful microorganisms, such as those that cause plant pathogenic diseases, particularly plant pathogenic fungi and bacteria.

[0196] Preferably, the formulation comprising the composition according to the invention may comprise from 0.01% to 90% by weight of the composition comprising components (A) and (B) and from 0% to 20% by weight of an agriculturally acceptable surfactant. Preferably, the formulation further comprises other active agents, more generally, in particular microbial and pest control agents.

[0197] Advantageously, the formulation further comprises 10% to 99.99% of solid or liquid inert agents, preservatives and / or adjuvants.

[0198] The present invention preferably also relates to a concentrated composition for dilution by a user, comprising a composition according to the invention or a formulation according to the invention, comprising 2% to 80% by weight, preferably between 5% and 70% by weight, of an active agent, which comprises at least the composition containing (A) and (B) and optionally other active agents.

[0199] The present invention preferably also relates to a seed dressing formulation for application to plant propagation material, comprising the composition according to the invention, and further comprising a diluent. Preferably, the seed dressing formulation is in the form of an aqueous suspension or a dry powder, exhibiting good adhesion to the plant propagation material. Preferably, the seed dressing formulation may comprise an active agent in an encapsulated form, preferably a sustained-release capsule and / or microcapsule.

[0200] The present invention preferably also relates to a method for combating and controlling plant pathogens, the method comprising applying a fungicide-effective amount of the composition according to the invention to the pest, the site of the pest, or the plant susceptible to the pest, in addition to methods for treating humans or animals by surgery or therapy and diagnostic methods performed on humans or animals.

[0201] The methods, compositions, and uses according to any one of the embodiments of the present invention are preferably used for controlling or preventing crops from being infected by plant pathogenic microorganisms resistant to other fungicides. Corynebacterium multiflorum Infection. "Resistant" to specific fungicides. Corynebacterium multiflorum This refers to, for example, the same as Corynebacterium multiflorum Compared to the expected sensitivity of fungal species, those less sensitive to fungicides... Corynebacterium multiflorum Fungal strains. Sensitivity is expected to be measured using, for example, strains that have not previously been exposed to fungicides. The term "effective" herein refers to an amount of active ingredient that demonstrates sufficient biocidal activity, such as at least 10%, more preferably at least 20%, even more preferably at least 50%, and still more preferably at least 70%, compared to a blind test. In this context, the compositions according to the invention preferably comprise at least 0.01 ppm, more preferably at least 0.025 ppm of the active ingredient, and 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 of the active ingredient.

[0202] According to the method or use described in any one of the embodiments of the present invention, it is preferably applied to plant crops, their sites, or their propagation material. It is preferably applied to plant pathogens, the sites of the plant pathogens, or plants susceptible to the plant pathogens, or their propagation material. The application of the compound as defined in any one of Examples 1 to 13 can be carried out according to any common application method (e.g., foliar application, irrigation application, soil application, furrow application, etc.).

[0203] In a preferred embodiment of the invention, the compound or pest-killing composition as defined herein is applied in the field to the leaves of the plant (foliar application), thereby allowing selection of the frequency and ratio of application to match the risk of infection by the pest in question. Alternatively, the active ingredient can reach the plant via the root system (systemic absorption), by irrigating the field with the liquid composition, or by introducing the active ingredient in solid form into the field (e.g., into the soil or furrows), such as in granular form. In the case of rice crops, such granules can be metered and added to the irrigated paddy field.

[0204] Compounds as defined in any of the embodiments of the present 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 those that have been genetically modified to produce biologically active compounds that control plant pest infestation.

[0205] Typically, compounds as defined in any of the embodiments according to the invention are used in the form of a composition containing a carrier (e.g., a formulation). The compounds and compositions thereof as defined in any of the embodiments of the present invention can be used in various forms, such as aerosol sprays, capsule suspensions, concentrated cold fogging agents, pulverizable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, encapsulated granules, fine granules, flowable concentrates for seed treatment, gases (under pressure), gas-producing products, granules, concentrated hot fogging agents, large granules, microparticles, oil-dispersible powders, oil suspension concentrates, oil-soluble liquids, pastes, plant sticks, powders for dry seed treatment, seeds coated with pesticides, soluble concentrates, soluble powders, solutions for seed treatment, suspension concentrates (flowable concentrates), ultra-low volume (ulV) liquids, ultra-low volume (ulV) suspensions, water-dispersible granules or tablets, water-dispersible powders for slurry treatment, water-soluble granules or tablets, water-soluble powders and wettable powders for seed treatment.

[0206] The compositions of the present invention, including all the embodiments disclosed above and their preferred examples, can be mixed with one or more other pest control agents, including additional fungicides, insecticides, nematicides, bactericides, acaricides, growth regulators, chemical sterilizers, chemical pheromones, insect repellents, attractants, pheromones, feeding stimulants, or other biologically active compounds to form multi-component pest control agents that provide even broader-spectrum agricultural protection.

[0207] Formulations typically comprise a liquid or solid carrier and optionally one or more commonly used formulation adjuvants, which may be solid or liquid adjuvants, such as unepoxidized or epoxidized vegetable oils (e.g., epoxidized coconut oil, rapeseed oil, or soybean oil), defoamers (e.g., silicone oil), preservatives, clay, inorganic compounds, viscosity modifiers, surfactants, binders, and / or thickeners. The composition may further comprise fertilizers, micronutrient donors, or other agents that influence plant growth, and may include combinations containing the compounds of the present invention and one or more other bioactive agents, such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides.

[0208] The composition is prepared in a manner known per se, in the absence of adjuvants, for example by grinding, sieving, and / or compressing the solid compound of the invention, and in the presence of at least one adjuvant, for example by tightly mixing and / or grinding the compound of the invention with one or more adjuvants. In the case of the solid compound of the invention, the grinding / milling of the compound is to ensure a specific particle size.

[0209] Examples of compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersants, direct sprayable or dilutable solutions, spreadable pastes, diluted emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules, or encapsulating agents in polymeric substances. These compositions—at least—contain a compound having formula (I) as defined herein, and the type of composition is selected to suit the intended purpose and the prevailing environment.

[0210] Typically, the composition comprises 0.1% to 99% (especially 0.1% to 95%) of compound (A) as defined in any one of the embodiments according to the invention and optionally compound (B), and 1% to 99.9% (especially 5% to 99.9%) of at least one solid or liquid carrier. It is also generally possible that 0% to 25% (especially 0.1% to 20%) of the composition is a surfactant (in each case, % means percentage by weight). While concentrated compositions are preferred for commercial purposes, end consumers typically use diluted compositions with significantly lower concentrations of the active ingredient.

[0211] Regarding compositions comprising component (A) and component (B); typically, the weight ratio of component (A) to component (B) is 2000:1 to 1:1000. The weight ratio of component (A) to component (B) is preferably 100:1 to 1:100; more preferably 20:1 to 1:50; even more preferably 12:1 to 1:25; even more preferably 10:1 to 1:10; still more preferably 5:1 to 1:15; and most preferably 2:1 to 1:5.

[0212] In addition to the potential synergistic effect relative to fungicidal activity, the compositions according to the invention may also have other unexpectedly advantageous properties. Examples of such advantageous properties that may be mentioned are: more favorable degradability; improved toxicological and / or ecotoxicological behavior; or improved characteristics of useful plants, including: emergence, crop yield, more developed root system, increased tillering, increased plant height, larger leaves, less basal leaf mortality, stronger tillering, greener leaf color, less fertilizer required, less seed required, more tillering, earlier flowering, earlier grain maturity, less lodging, enhanced bud growth, improved plant vigor, and earlier germination.

[0213] Additional beneficial effects could include suppressing or reducing the development of resistance to a particular active ingredient, which may be particularly beneficial through combinations that may have one or more different modes of action.

[0214] Some compositions according to the present invention have systemic action and can be used as fungicides for leaf, soil and seed treatment.

[0215] Using the composition according to the invention, plant pathogenic microorganisms present on various useful plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) can be inhibited or destroyed, while also protecting later-growing plant parts from invasion by plant pathogenic microorganisms.

[0216] The compositions according to the invention can be applied to plant pathogenic microorganisms, useful plants threatened by microbial invasion, their sites, their propagation materials, stored goods or technical materials.

[0217] The composition according to the invention can be applied before or after useful plants, their propagation materials, stored goods or technical materials are infected by microorganisms.

[0218] The amount of the composition according to the invention to be applied will depend on a variety of factors, such as the compound used; the object to be treated, such as plants, soil or seeds; the type of treatment, such as spraying, dusting or seed dressing; the purpose of the treatment, such as prevention or treatment; the type of fungus to be controlled or the time of application.

[0219] When applied to useful plants in combination with component (B) of 1 to 5000 g ai / ha, particularly 2 to 2000 g ai / ha, for example 100, 250, 500, 800, 1000, or 1500 g ai / ha, component (A) is typically applied at a ratio of 5 to 2000 g ai / ha, particularly 10 to 1000 g ai / ha, for example 50, 75, 100, or 200 g ai / ha.

[0220] The compounds defined in any of the embodiments of the present invention are preferably used for pest control at a rate of 1 to 500 g / ha, preferably 50-300 g / ha.

[0221] Preferably, compounds having formula (I) as defined in any embodiment of the invention are used for pest control at a ratio of 10 to 200 g / ha, preferably 15 to 100 g / ha, more preferably 20 to 80 g / ha, most preferably 30 to 60 g / ha, such as 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75 or 80 g ai / ha.

[0222] In some embodiments of the invention, compounds having formula (I) as defined in any of the embodiments of the invention and biocidal compositions containing these compounds are applied at a ratio of 10 to 80 g ai / ha, preferably 15 to 65 g ai / ha, more preferably 20 to 60 g ai / ha, and even more preferably 35 to 45 g ai / ha, such as 10, 20, 25, 30, 35, 40, 45 or 60 g ai / ha.

[0223] In an embodiment of the method according to the invention, the compound according to formula (I) is applied at a rate of at least 10 g / ha, preferably at least 10, 15, 20, 25, 30, 35, or 40 g / ha.

[0224] In embodiments of the method according to the invention, the compound according to formula (I) is applied at a rate of up to 80 g / ha, preferably up to 80, 75, 70, 65, 60, 55, 50 or 45 g / ha.

[0225] As used herein, the term "g ai / ha" refers to the application ratio given in grams [g] of active ingredient [ai] per unit surface area [ha]. The unit hectare (symbol ha) is equal to a hectare with a side length of 100 m (1 hm²). 2 The hectare is a metric unit of area, representing a square area of ​​10,000 square meters or 10,000 square meters. The hectare is a commonly used unit of area in the metric system.

[0226] In agricultural practice, the application rate of the composition according to the invention depends on the type of effect desired and typically ranges from 20 to 4000 g of total composition per hectare.

[0227] When the composition according to the invention is used to treat seeds, a ratio of 0.001 to 50 g of component (A) compound / kg seed, preferably 0.01 to 10 g / kg seed, and preferably 0.001 to 50 g of component (B) compound / kg seed, preferably 0.01 to 10 g / kg seed, is generally sufficient.

[0228] Examples of leaf formulations used in premixed compositions are:

[0229] GR: Granules

[0230] WP: Wettable powder

[0231] WG: Water-dispersible granules (powders)

[0232] SG: Water-soluble granules

[0233] SL: Soluble Concentrate

[0234] EC: Emulsifiable concentrate

[0235] DC: Dispersible concentrate

[0236] EW: Oil-in-water emulsion

[0237] ME: Microemulsion

[0238] SC: Aqueous suspension concentrate

[0239] CS: Aqueous Capsule Suspension

[0240] OD: Oil-based suspension concentrate, and

[0241] SE: Aqueous suspension emulsion.

[0242] Examples of seed-treated formulations used in premixed compositions include:

[0243] WS: Wettable powder for seed treatment slurry

[0244] LS: Solution for seed treatment

[0245] ES: Emulsion for seed treatment

[0246] FS: Suspension concentrate for seed treatment

[0247] WG: Water-dispersible granules, and

[0248] CS: Aqueous capsule suspension.

[0249] Examples of formulation types suitable for barrel-mixing compositions are solutions, diluted emulsions, suspensions, or mixtures thereof, as well as dusts.

[0250] Depending on the properties of the formulation, the application method can be selected according to the intended purpose and the environment at the time (such as foliar application, soaking application, spraying application, atomizing application, dusting application, broadcasting application, coating application, or watering application).

[0251] Barrel-mixed compositions are typically prepared by diluting one or more premixed compositions containing different biocides and optionally additional adjuvants with a solvent (e.g., water).

[0252] Suitable carriers and auxiliaries can be solid or liquid and are substances commonly used in formulation technology, such as natural or recycled minerals, solvents, dispersants, wetting agents, thickeners, binders, or fertilizers.

[0253] Typically, tank-mixed products for foliar or soil application contain 0.1% to 20%, especially 0.1% to 15%, of the desired ingredient and 99.9% to 80%, especially 99.9% to 85%, of solid or liquid adjuvants (including, for example, diluents or solvents, such as water), wherein the adjuvants may be surfactants, in amounts based on 0% to 20%, especially 0.1% to 15%, of the tank-mixed product.

[0254] Typically, premixed formulations for foliar application contain 0.1% to 99.9%, especially 1% to 95% of the desired ingredient and 99.9% to 0.1%, especially 99% to 5% of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvants may be surfactants, in amounts based on 0% to 50%, especially 0.5% to 40% of the premixed formulation.

[0255] Typically, tank-mixed products for seed treatment application contain 0.25% to 80%, especially 1% to 75% of the desired ingredient and 99.75% to 20%, especially 99% to 25% of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvants may be surfactants, in amounts based on 0% to 40%, especially 0.5% to 30% of the tank-mixed product.

[0256] Typically, premixed formulations for seed treatment application contain 0.5% to 99.9%, especially 1% to 95% of the desired ingredient and 99.5% to 0.1%, especially 99% to 5% of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvants may be surfactants, in amounts based on 0% to 50%, especially 0.5% to 40% of the premixed formulation.

[0257] Commercial products will preferably be formulated as concentrates (e.g., premixed compositions (formulations)), while end users will typically use diluted formulations (e.g., barrel-mixed compositions).

[0258] Preferred seed treatment premixes are aqueous suspension concentrates. The formulation can be applied to seeds using conventional treatment techniques and machinery, such as fluidized bed technology, drum milling methods, rotostatic seed processors, and drum coating machines. Other methods (such as spray beds) can also be useful. Seeds can be pre-sized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art. The compounds of the present invention are particularly suitable for use in soil and seed treatment applications. Typically, the premixed compositions of the present invention contain 0.5% to 99.9%, especially 1% to 95%, advantageously 1% to 50% by weight of the desired ingredient and 99.5% to 0.1%, especially 99% to 5% by weight of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvants (or auxiliaries) can be surfactants, in amounts based on the mass of the premixed formulation, from 0% to 50%, especially 0.5% to 40% by weight.

[0259] Furthermore, other biocidal active ingredients or compositions may be combined with the compositions of the present invention and used in the methods of the present invention, and applied simultaneously or sequentially with the compositions of the present invention. When applied simultaneously, these additional active ingredients may be formulated or mixed together with the compositions of the present invention, for example, in a spray can. These additional biocidal active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides, and / or plant growth regulators.

[0260] Additionally, the compositions of the present invention can be administered in combination with one or more systemically acquired resistance inducers (“SAR” inducers). SAR inducers are known and described, for example, in U.S. Patent No. 6,919,298, and include, for example, salicylates and the commercial SAR inducer aramid-benzene-S-methyl.

[0261] The compounds as defined in any of the embodiments of the invention are typically used in the form of a composition and can be applied simultaneously or sequentially with other compounds to the crop area or plant to be treated. For example, these other compounds may be fertilizers or micronutrient donors or other formulations that affect plant growth. They may also be selective or non-selective herbicides, and insecticides, fungicides, bactericides, nematicides, molluscicides, or mixtures of several of these formulations, if desired, together with other carriers, surfactants, or application-promoting adjuvants commonly used in the field of formulations.

[0262] Compounds having formula (I) can be used to control or protect against one or more plant pathogens. Multi-master SporesThe (fungicide) compositions are used as active ingredients, comprising at least one compound as defined in any one of the embodiments of the invention (in free form or in the form of an agrochemically available salt) and at least one of the above-mentioned adjuvants.

[0263] The plants and / or target crops according to the invention include conventional and genetically enhanced or genetically engineered varieties, such as insect-resistant varieties (e.g., Bt. and VIP varieties), disease-resistant and herbicide-tolerant varieties (e.g., glyphosate- and glufosinate-resistant corn varieties, commercially available under the trademarks RoundupReady® and LibertyLink®), and nematode-tolerant varieties. By way of example, suitable genetically enhanced or genetically engineered crop varieties include Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.

[0264] The terms “plant” and / or “target crop” should be understood to also include plants that have developed tolerance to herbicides (like bromonazine) or herbicide classes (e.g., HPPD inhibitors, ALS inhibitors such as flusulfuron, flusulfuron-methyl, and triflusulfuron-methyl, EPSPS (5-enol-pyruvyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthase) inhibitors, or PPO (protoporphyrinogen-oxidase) inhibitors) through conventional breeding or genetic engineering. An example of a crop that has been conditioned to tolerate imidazolinones (e.g., methoxyfenozide) through conventional breeding (mutation) is Clearfield® Summer Canola (Canola). Examples of crops that have been conditioned to tolerate herbicides or herbicide classes through genetic engineering include glyphosate-resistant and glufosinate-resistant maize varieties commercially available under the trademarks RoundupReady®, Herculex I®, and LibertyLink®.

[0265] The terms "plant" and / or "target crop" should be understood to include those that are naturally or have been conditioned to be resistant to harmful insects. This includes plants transformed, for example, by using recombinant DNA technology to synthesize one or more selectively acting toxins, as known from, for example, toxin-producing bacteria. Examples of toxins that can be expressed include - Endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins from nematode-parasitic bacteria, and toxins produced by scorpions, arachnids, wasps, and fungi. [The following appears to be a separate, unrelated sentence:] ... Bacillus thuringiensis ( Bacillus thuringiensisAn example of a crop containing an insecticide is Bt corn KnockOut® (Syngenta Seeds). An example of a crop containing more than one gene encoding insecticidal resistance and thus expressing more than one toxin is VipCot® (Syngenta Seeds). Crops or their seed material can also be resistant to multiple types of pests (a so-called superimposed transgenic event when produced through genetic modification). For example, plants can express insecticidal proteins while also being resistant to herbicides, such as Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).

[0266] The terms “plant” and / or “target crop” should be understood to also include plants that have been transformed using recombinant DNA technology to synthesize selectively active resistance substances, such as so-called “pathogenic mechanism-associated proteins” (PRPs, see, for example, EP 0392225 A). Examples of such resistance substances and transgenic plants capable of synthesizing such resistance substances are known, for example, from EP 0392225 A, WO 95 / 33818, and EP 0353191 A. Methods for producing such transgenic plants are generally known to those skilled in the art and are described in, for example, the disclosures mentioned above.

[0267] Toxins that can be expressed by genetically modified plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus thuringiensis; or insecticidal proteins from Bacillus thuringiensis, such as... - Endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C; or vegetative insecticidal proteins (Vip), such as Vip1, Vip2, Vip3, or Vip3A; or insecticidal proteins of nematode-parasitic bacteria, such as species of *Photorhabdus* spp. or species of *Xenorhabdus* spp., such as *Photorhabdus luminescens* and *Xenorhabdus* spp. (nematophilus); toxins produced by animals, such as scorpion venom, spider venom, bee venom, and other insect-specific neurotoxins; toxins produced by fungi, such as streptotoxins; lectins, such as pea lectin, barley lectin, or snowdrop lectin; agglutinin; protease inhibitors, such as trypsin inhibitors, serine inhibitors, potato glycoproteins, cystatin, and papain inhibitors; ribosome-inactivating proteins (RIPs), such as ricin, maize-RIP, absinthecin, loofah seed toxin, saponin toxin, or scutellarin; steroid metabolic enzymes, such as 3-hydroxysteroid oxidase, decidual steroid-UDP-glycosyltransferase, cholesterol oxidase, decidualin inhibitors, HMG-COA-reductase, ion channel blockers such as sodium or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase, and glucanase.

[0268] Furthermore, in the context of this invention, it should be understood that Endotoxins (e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C) or vegetative insecticidal proteins (Vip) (e.g., Vip1, Vip2, Vip3, or Vip3A) obviously also include mixed toxins, truncated toxins, and modified toxins. Mixed toxins are generated through novel recombination of different combinations of the different domains of those proteins (see, for example, WO 02 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are substituted. In such amino acid substitutions, a non-naturally occurring protease recognition sequence is preferably inserted into the toxin, for example, as in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0269] Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, for example, in EP-A-0 374753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878 and WO 03 / 052073.

[0270] Methods for preparing such transgenic plants are generally known to those skilled in the art and are described in, for example, the disclosures mentioned above. CryI type deoxyribonucleic acid and its preparation are known, for example, from WO 95 / 34656, EP-A-0 367474, EP-A-0 401 979 and WO 90 / 13651.

[0271] Toxins contained in genetically modified plants confer tolerance to harmful insects. These insects can exist in any insect taxonomy, but are particularly common in beetles (Coleoptera), dipterans (Diptera), and moths (Lepidoptera).

[0272] Transgenic plants containing one or more genes encoding insecticidal resistance and expressing one or more toxins are known, and some of them are commercially available. Examples of such plants are: YieldGard® (a corn variety expressing Cry1Ab toxin); YieldGard Rootworm® (a corn variety expressing Cry3Bb1 toxin); YieldGard Plus® (a corn variety expressing both Cry1Ab and Cry3Bb1 toxins); Starlink® (a corn variety expressing Cry9C toxin); Herculex I® (a corn variety expressing Cry1Fa2 toxin and the enzyme phosphatidylin N-acetyltransferase (PAT) for acquiring resistance to the herbicide glufosinate); NuCOTN 33B® (a cotton variety expressing Cry1Ac toxin); Bollgard I® (a cotton variety expressing Cry1Ac toxin); Bollgard II® (cotton variety expressing Cry1Ac and Cry2Ab toxins); VipCot® (cotton variety expressing Vip3A and Cry1Ab toxins); NewLeaf® (potato variety expressing Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate resistance trait), Agrisure® CBAdvantage (Bt11 corn borer (CB) trait), and Protecta®.

[0273] Other examples of such genetically modified crops are:

[0274] 1. Bt11 maize, from Syngenta Seeds SAS, Cheminde l'Hobit 27, F-31 790 St. Sauveur, France, Registry No. C / FR / 96 / 05 / 10. A genetically modified maize variety that expresses a truncated Cry1Ab toxin, resulting in resistance to the European corn borer (…). Corn borer ( Ostrinia nubilalis )and Powder stem borer ( Sesamia nonagrioides Bt11 corn was also genetically modified to express PAT enzymes to gain tolerance to the herbicide glufosinate.

[0275] 2. Bt176 maize, from Syngenta Seed Company, 27 Hobbit Road, F-31 790 Saint-Soville, France, Registry No. C / FR / 96 / 05 / 10. Genetically modified maize that expresses the Cry1Ab toxin through transgenic expression, resulting in resistance to the European corn borer (…). Corn borer and Powder stem borer Bt176 corn was also genetically modified to express PAT enzymes to gain tolerance to the herbicide glufosinate.

[0276] 3. MIR604 corn, from Syngenta Seed Company, 27 Hobbit Road, F-31 790 Saint-Soville, France, Registry No. C / FR / 96 / 05 / 10. Insect-resistant corn borne by transgenic expression of a modified Cry3A toxin. This toxin is modified by inserting a cathepsin-G-protease recognition sequence, Cry3A055. The preparation of this type of transgenic corn plant is described in WO 03 / 018810.

[0277] 4. MON 863 corn, from Monsanto Europe SA, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 It expresses the Cry3Bb1 toxin and is resistant to certain Coleoptera insects.

[0278] 5. IPC 531 cotton, from Monsanto Europe 270-272, Boulevard de Teveren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0279] 6.1507 maize, from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, Registry No. C / NL / 00 / 10. Genetically modified maize expressing the protein Cry1F to acquire resistance to certain lepidopteran insects and expressing the PAT protein to acquire tolerance to the herbicide glufosinate.

[0280] 7. NK603 × MON 810 maize, from Monsanto Europe, 270-272 Teflon Boulevard, B-1150 Brussels, Belgium, Registry No. C / GB / 02 / M3 / 03. Composed of conventionally bred hybrid maize varieties through crossing the genetically modified cultivar NK603 and MON 810. Transgenic expression of NK603 × MON 810 maize was achieved by... Agrobacterium ( Agrobacterium sp. The protein CP4 EPSPS obtained from strain CP4 conferred resistance to the herbicide Roundup® (containing glyphosate), and also expressed proteins derived from strain CP4. Bacillus thuringiensis Kurstak subsp. ( Bacillus thuringiensis subsp. kurstaki The Cry1Ab toxin obtained from it conferred tolerance to certain lepidopteran insects, including the European corn borer.

[0281] As used herein, the term "site" means the place in which or on which a plant grows, or the place where the seeds of a cultivated plant are sown, or the place where the seeds will be placed in the soil. It includes soil, seeds and seedlings, and established vegetation.

[0282] The term "plant" refers to all the tangible parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, culms, leaves, and fruits.

[0283] The term "plant propagation material" should be understood to refer to the reproductive parts of a plant, such as seeds, which can be used for plant propagation, as well as vegetarian material, such as cuttings or tubers (e.g., potatoes). References may include, for example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts of the plant. References may also include germinating plants and young plants that will be transplanted after germination or emergence. These young plants can be protected before transplanting by complete or partial treatment via maceration. Preferably, "plant propagation material" should be understood to mean seeds.

[0284] The pesticides referred to in this article by their common names are, for example, those known from "The Pesticide Manual", 15th edition, British Crop Protection Council 2009.

[0285] The compound used in the method of the invention as defined in any of the embodiments of the invention may be the sole active ingredient of the composition, or it may be blended with one or more additional active ingredients (such as pest control agents, fungicides, synergists, herbicides, or plant growth regulators) where appropriate. In some cases, the additional active ingredients may produce unexpected synergistic activity.

[0286] The compositions according to the invention may also contain additional solid or liquid adjuvants, such as stabilizers, for example un-epoxidized or epoxidized vegetable oils (e.g., epoxidized coconut oil, rapeseed oil, or soybean oil), defoamers (e.g., silicone oil), preservatives, viscosity modifiers, binders and / or thickeners, fertilizers, or other active ingredients for achieving specific effects, such as bactericides, fungicides, nematicides, plant activators, molluscicides, or herbicides.

[0287] The compounds and compositions according to the invention are prepared in a manner known per se, in the absence of adjuvants, for example by grinding, sieving, and / or compressing solid active ingredients; and in the presence of at least one adjuvant, for example by tightly mixing the active ingredient with one or more adjuvants and / or grinding the active ingredient together with one or more adjuvants. These methods for preparing the compositions and the use of the compounds (I) for preparing these compositions are also the subject of this invention.

[0288] Another aspect of the invention relates to the use of compounds as defined in any one of the embodiments of the invention, compositions comprising at least one compound as defined in any one of the embodiments of the invention, or fungicides or insecticides comprising at least one compound as defined in any one of the embodiments of the invention, mixed with other fungicides or insecticides as described above, for the control or prevention of infection of plants (e.g., plants, such as crop plants), their reproductive material (e.g., seeds), harvested crops (e.g., harvested food crops), or inanimate materials by insects or plant pathogenic microorganisms (preferably fungal organisms).

[0289] Another aspect of the invention relates to a method for controlling or preventing the infection of plants (e.g., plants, such as crop plants), their propagation material (e.g., seeds), harvested crops (e.g., harvested grain crops), or inanimate materials by plant pathogenic microorganisms or putrefactive microorganisms or organisms potentially harmful to humans (especially fungal organisms), the method comprising applying a compound as an active ingredient, as defined in any one of the embodiments of the invention, to these plants, parts of these plants or their sites, their propagation material, or any part of these inanimate materials.

[0290] Control or prevention means reducing the infestation of insect or plant pathogenic microorganisms or putrefactive microorganisms or potentially harmful organisms (especially fungal organisms) to a level that has been proven to be improved.

[0291] A preferred method for controlling or preventing crop infection by plant pathogenic microorganisms (especially fungal organisms) or insects is foliar application, which includes applying a compound as defined in any one of the embodiments of the invention, or an agricultural chemical composition containing at least one of said compounds. The frequency and rate of application will depend on the risk of infection by the corresponding pathogen or insect.

[0292] However, compounds having formula (I), preferably combined with compound (B), can also penetrate plants via the soil through roots (systemic absorption) by irrigating the plant site with a liquid formulation or by applying the compound in solid form, such as in granular form, to the soil (soil application). In rice crops, such granular formulations can be applied to irrigated paddy fields. Compounds having formula (I) can also be applied to seeds by impregnating seeds or tubers with a liquid formulation of a fungicide or by coating them with a solid formulation (coating).

[0293] Further features of the preferred binary composition comprising a compound having formula (I), the method of applying it to grains and the ratio of its application are as described for a composition comprising a compound having formula (I) and, preferably, at least one component (B) as described above.

[0294] Their application can be performed before or after the plants or parts thereof are infected by fungi. Preferably, treatment is carried out before infection. When a compound having formula (I) is used on its own, the application rate in the method according to the invention is as described above, for example, a typical rate of 5 to 2000 g ai / ha, particularly 10 to 1000 g ai / ha, such as 50, 75, 100 or 200 g ai / ha. During the growing season, a compound having formula (I) can be applied to these plants once or more.

[0295] For use in the method according to the invention, compounds having formula (I) can be converted into conventional formulations as described above, such as solutions, emulsions, suspensions, dusts, powders, pastes, and granules. The form of use will depend on the specific intended purpose; in each case, a fine and uniform distribution of the compound having formula (I) should be ensured.

[0296] As used in this article, the term "plant" includes seedlings, shrubs, and crops of fruits and vegetables.

[0297] Example

[0298] The invention will now be illustrated by the following non-limiting examples. All cited references are incorporated herein by reference.

[0299] The same formulation can be used in compositions containing only compounds of formula (I) as active ingredients.

[0300] The following examples are provided to illustrate the invention and are not intended to limit the invention in any way.

[0301] The compounds of the present invention differ from known compounds in that they have greater efficacy at lower application rates, which can be verified by those skilled in the art using the experimental procedures outlined in the examples.

[0302] Compounds having formula (I) can have many benefits, including, in particular, favorable levels of biological activity for protecting plants from fungal diseases or superior properties for use as active ingredients in agrochemicals (e.g., higher biological activity, favorable activity spectrum, increased safety (including improved crop tolerance), improved physicochemical properties, or increased biodegradability).

[0303] Examples of preparations

[0304]

[0305] The combination is thoroughly mixed with these adjuvants and the mixture is thoroughly ground in a suitable mill to obtain a wettable powder that can be diluted with water to give a suspension of the desired concentration.

[0306]

[0307] The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill to obtain a powder that can be used directly for seed treatment.

[0308] Emulsifiable concentrate

[0309]

[0310] Emulsions with any required dilution that can be used in plant protection can be obtained by diluting the concentrate with water.

[0311]

[0312] A ready-to-use powder is obtained by mixing the mixture with a carrier and grinding the mixture in a suitable mill. This type of powder can also be used in the dry mixing of seeds.

[0313] Extruder granules

[0314]

[0315] The mixture is combined with these additives and ground, and then the mixture is moistened with water. The mixture is extruded and then dried in an air stream.

[0316] Coated granules

[0317]

[0318] The finely ground mixture is uniformly applied to kaolin moistened with polyethylene glycol in a mixer. This process yields dust-free coated granules.

[0319] suspension concentrate

[0320]

[0321] The finely ground compound is tightly mixed with adjuvants to produce a suspension concentrate, from which a suspension concentrate can be diluted with water to obtain a suspension of any desired dilution. Using such a dilution, living plants and plant propagation material can be treated and protected from microbial contamination by spraying, watering, or immersion.

[0322] Flowable concentrate for seed treatment

[0323]

[0324] The finely ground compound is tightly mixed with adjuvants to produce a suspension concentrate, from which a suspension concentrate can be diluted with water to obtain a suspension of any desired dilution. Using such a dilution, living plants and plant propagation material can be treated and protected from microbial contamination by spraying, watering, or immersion.

[0325] Sustained-release capsule suspension

[0326] 28 parts of the mixture were combined with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). This mixture was emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of an antifoaming agent, and 51.6 parts of water until the desired particle size was achieved. 2.8 parts of a mixture of 1,6-hexanediamine and 5.3 parts of water were added to this emulsion. The mixture was stirred until polymerization was complete. The resulting capsule suspension was stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. This capsule suspension formulation contained 28% of the active ingredient. The diameter of the medium capsules was 8-15 micrometers. The resulting formulation was applied as an aqueous suspension to seeds in a suitable apparatus for this purpose.

[0327] Formulation types include emulsion concentrates (EC), suspension concentrates (SC), suspension emulsions (SE), capsule suspensions (CS), water-dispersible granules (WG), emulsifiable granules (EG), water-in-oil emulsions (EO), oil-in-water emulsions (EW), microemulsions (ME), oil dispersions (OD), oil suspensions (OF), oil-soluble liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), technical grade (TK), dispersible concentrates (DC), wettable powders (WP), soluble granules (SG), or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0328] abbreviation

[0329]

[0330] Preparation Examples

[0331] The compounds having formula (I) according to the present invention can be prepared using the synthesis techniques described above and below.

[0332] “Mp” refers to the melting point in °C. The free radical indicates a methyl group. Recorded on a Bruker 400 MHz spectrometer (or 600 MHz as indicated). 1 H NMR and 19 F NMR measurements, chemical shift is relative to TMS (F NMR values, chemical shift is relative to TMS). 1 H) and CFCl3 ( 19 F) Standards are given in ppm. Spectra are measured in deuterated solvents as indicated.

[0333] Example P1: N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropane Preparation of alkylformamides (compounds having formula IA)

[0334] (IA)

[0335] Step 1: Preparation of N-methoxycyclopropane formamide

[0336]

[0337] Within 30 minutes, to O 2,8-methylhydroxylamine (0.80 g, 21.8 mmol) and potassium carbonate (0.52 mL, 2.88 mmol) were added dropwise to a solution of EtOAc (7.7 mL) cooled in an ice bath, followed by the addition of cyclopropanecarbonyl chloride (2.0 g, 18.2 mmol). The ice bath was removed, and the contents were stirred for 2 hours. Then, EtOH (5 mL) was added, and the reaction mixture was stirred for 30 min. The solid was filtered and dried under vacuum to give 2.14 g of N-methoxycyclopropaneformamide as a white solid. 1 H NMR (400 MHz, DMSO-) d 6 ) δ ppm: 11.13 (s, 1H), 3.57 (s, 3H), 1.34 (m, 1H), 0.87 (m,1H), 0.68 (m, 3H).

[0338] Step 2: Preparation of N-[(4-cyanophenyl)methyl]-N-methoxy-cyclopropaneformamide

[0339]

[0340] Potassium carbonate (0.80 g, 5.50 mmol) was added to a solution of N-methoxycyclopropaneformamide (0.67 g, 5.50 mmol) in acetonitrile (10 mL), followed by the addition of 4-(bromomethyl)benzyl nitrile (1.0 g, 5.50 mmol). The reaction mixture was heated at 60°C for 8 hours and then cooled to room temperature. The reaction mixture was then diluted with water and extracted with EtOAc. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting crude residue was purified by silica gel rapid chromatography (cyclohexane / EtOAc eluent gradient 1:0 to 7:3) to give 1.0 g of N-[(4-cyanophenyl)methyl]-N-methoxy-cyclopropaneformamide as a pale yellow oil. 1 H NMR (400 MHz, CDCl3) δ ppm: 7.61(d, 2H), 7.42 (d, 2H), 4.84 (s, 2H), 3.74 (s, 3H), 2.18 (m, 1H), 1.04 (m,2H), 0.89 (m, 2H).

[0341] Step 3: Preparation of N-[[4-(N-hydroxymethylamidinyl)phenyl]methyl]-N-methoxy-cyclopropaneformamide

[0342]

[0343] A solution of N-[(4-cyanophenyl)methyl]-N-methoxy-cyclopropaneformamide (0.50 g, 2.30 mmol) in EtOH (2.5 mL) was added to a solution of N-[(4-cyanophenyl)methyl]-N-methoxy-cyclopropaneformamide (0.18 mL, 2.99 mmol). The reaction mixture was stirred at 80°C for 2 hours, cooled to 25°C, and concentrated under reduced pressure. The resulting residue was alkalized to pH 8 by adding 30% NaOH aqueous solution and extracted with EtOAc. The total combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to give 270 mg of N-[[4-(N-hydroxymethylamidine)phenyl]methyl]-N-methoxy-cyclopropaneformamide as a white solid. 1 H NMR (400MHz, DMSO- d 6 ) δ ppm: 9.60 (s, 1H), 7.62 (d, 2H), 7.28 (d, 2H), 5.77 (s, 2H), 4.55 (s, 2H), 3.71 (s, 3H), 2.17 (m, 1H), 0.82 (m, 4H).

[0344] Step 4: N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropane Preparation of alkyl-formamides (compounds having formula (IA))

[0345] N-[[4-(N-hydroxymethylammonium)phenyl]methyl]-N-methoxy-cyclopropaneformamide (1.05 g, 4.00 mmol), EtOAc (20 mL), and pyridine (0.49 mL, 6.0 mmol) were added to a 30 mL Schlenk tube (connected to trap-1 (empty), then to trap-2 (filled with 4 N NaOH aqueous solution)). The resulting reaction mixture was stirred at room temperature for 10 min and cooled to 0°C. 2,2,2-trifluoroacetyl chloride (0.58 g, 4.40 mmol) was slowly added to the resulting white suspension. The reaction mixture became colorless after stirring at 25°C, and after 1 hour, the reaction mixture was diluted with EtOAc. The resulting organic phase was washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give 1.26 g of N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide (a compound having formula (IA)) as an orange oil, which solidified during storage. mp: 35°C–38°C, LC / MS (Method A) retention time = 0.99 min, 316.3 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm: 8.09 (d, 2H), 7.53 (d, 2H), 4.87 (s, 2H), 3.73 (s, 3H), 2.19 (m, 1H), 1.05 (m, 2H), 0.86 (m, 2H). 19 F NMR (400MHz, CDCl3) δ ppm: -65.33 (s).

[0346] Example P2: N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl] Preparation of Acrylamide (a compound having formula (IB))

[0347] (IB)

[0348] Step 1: Preparation of 2-methoxypropionyl chloride

[0349]

[0350] Oxaloyl chloride (0.90 mL, 10.1 mmol) was added dropwise to a solution of 2-methoxypropionic acid (0.70 g, 6.72 mmol), dimethylformamide (0.005 mL), and dichloromethane, cooled in an ice bath. After 30 min, the ice bath was removed, and stirring was continued for 3.5 h. The reaction mixture was then concentrated under slightly reduced pressure (approximately 500 mbar) to give 200 mg of 2-methoxypropionyl chloride, which was used directly for the next conversion without further purification. The same conditions can be used to introduce single enantiomers of 2-methoxypropionic acid, i.e., (R)- or (S)-enantiomers, to obtain the corresponding single enantiomers of 2-methoxypropionyl chloride.

[0351] Step 2: Preparation of 4-[(methoxyamino)methyl]benzyl nitrile hydrochloride

[0352]

[0353] O-methylhydroxylamine hydrochloride (1.7 g, 20.4 mmol) and potassium carbonate (3.0 g, 21.4 mmol) were added to a solution of 4-(bromomethyl)benzyl nitrile (2.0 g, 10.2 mmol) in acetonitrile (10 mL). After 17 hours, the reaction mixture was decanted into water and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting crude residue was absorbed in tert-butyl methyl ether (15 mL), cooled to 0°C in an ice bath, and 4 M HCl (2.2 mL) in dioxane was added dropwise. After 10 min, the ice bath was removed, and the crude contents were stirred at room temperature for 2 hours. The solid was collected by filtration, washed with tert-butyl methyl ether, and dried under vacuum to give 1.6 g of 4-[(methoxyamino)methyl]benzyl nitrile hydrochloride as a white solid, which was used for the next conversion without further purification. 1 H NMR (400MHz, DMSO- d 6 ) δ ppm: 7.90 (d, 2H), 7.72 (d, 2H), 4.41 (s, 2H), 3.75 (s, 3H).

[0354] Step 3: Preparation of N-[(4-cyanophenyl)methyl]-N,2-dimethoxy-propionamide

[0355]

[0356] At 0°C, 2-methoxypropionyl chloride (0.20 g, 1.63 mmol in 10 mL DCM solution) was added dropwise to a suspension of 4-[(methoxyamino)methyl]benzyl nitrile hydrochloride (0.33 g, 1.63 mmol) and sodium bicarbonate (0.42 g, 4.90 mmol) in dichloromethane (25 mL). After 10 min, the ice bath was removed, and the reaction mixture was stirred for 15 min. The resulting solid was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting crude residue was purified by silica gel rapid chromatography (cyclohexane / EtOAc eluent gradient 99:1 to 1:1) to provide 155 mg of N-[(4-cyanophenyl)methyl]-N,2-dimethoxy-propionamide as a colorless oil. The same conditions can be used to introduce a single enantiomer of 2-methoxypropionyl chloride, i.e., (R)- or (S)-enantiomer, to obtain the corresponding single enantiomer of N-[(4-cyanophenyl)methyl]-N,2-dimethoxy-propionamide. 1H NMR (400 MHz, CDCl3) δ ppm: 7.65 (d, 2H), 7.45(d, 2H), 4.95 (m, 1H), 4.72 (m, 1H), 4.25 (q, 1H), 3.70 (s, 3H), 3.36 (s,3H), 1.35 (d, 3H).

[0357] Step 4: Preparation of N-[[4-(N-hydroxymethylammonium)phenyl]methyl]-N,2-dimethoxy-propionamide

[0358]

[0359] A solution of N-[(4-cyanophenyl)methyl]-N,2-dimethoxy-propionamide (1.0 g, 4.03 mmol) in EtOH (5 mL) was added to a solution of N-[(4-cyanophenyl)methyl]-N,2-dimethoxy-propionamide (0.3 mL, 4.29 mmol). The reaction mixture was stirred at 60°C for 3 hours, cooled to room temperature, and concentrated under reduced pressure. The resulting residue was alkalized to pH 8 by adding 30% NaOH aqueous solution and extracted with EtOAc. The combined organic phases were concentrated under reduced pressure and dried to give 270 mg of N-[[4-(N-hydroxymethylamidine)phenyl]methyl]-N,2-dimethoxy-propionamide as a white solid, which was used for the next transformation without further purification. The same conditions can be used to introduce a single enantiomer of N-[(4-cyanophenyl)methyl]-N,2-dimethoxy-propionamide, i.e., (R)- or (S)-enantiomers, to obtain the corresponding single enantiomers of N-[[4-(N-hydroxymethylammonium)phenyl]methyl]-N,2-dimethoxy-propionamide. 1 H NMR (400 MHz, DMSO- d 6 ) δ ppm: 9.59 (s,1H), 7.63 (d, 2H), 7.25 (d, 2H), 5.77 (s, 2H), 4.88 (s, 1H), 4.71 (m, 1H),4.25 (q, 1H), 3.69 (m, 3H), 3.21 (s, 3H), 1.20 (d, 3H).

[0360] Step 5: N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propane Preparation of enamides (compounds having formula (IB))

[0361] N-[[4-(N-hydroxymethylammonium)phenyl]methyl]-N,2-dimethoxy-propionamide (1.0 g, 3.34 mmol), EtOAc (20 mL), and pyridine (0.41 mL, 5.0 mmol) were added to a 30 mL Schlenk tube (connected to trap-1 (empty), then to trap-2 (filled with 4 N NaOH aqueous solution)). The reaction mixture was stirred at room temperature for 10 min and then cooled via an ice bath. 2,2,2-trifluoroacetyl chloride (0.49 g, 3.68 mmol) was added dropwise to the resulting white suspension. The ice bath was removed, and the reaction mixture became a colorless solution after stirring at room temperature. After stirring at room temperature for 1 hour, the reaction mixture was diluted with EtOAc, washed with water, dried over sodium sulfate, and concentrated under reduced pressure to give 1.26 g of N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acrylamide (a compound having formula (IB)) as a white solid. mp: 62°C–65°C, LC / MS (Method A) retention time = 1.02 min, 360.6 (M+H). A single enantiomer of N-[[4-(N-hydroxymethylammonium)phenyl]methyl]-N,2-dimethoxy-propionamide, i.e., (R)- or (S)-enantiomers, can be introduced under the same conditions to give the corresponding single enantiomers of the compound having formula (IB). 1 H NMR (400 MHz, CDCl3) δ ppm: 8.09 (d, 2H), 7.48 (d, 2H), 4.98 (m, 1H), 4.80 (m, 1H), 4.27 (m, 1H), 3.71 (s, 3H), 3.34 (s, 3H), 1.37(d, 3H). 19 F NMR (400 MHz, CDCl3) δ ppm: -65.35 (s).

[0362] Biological examples

[0363] The following examples are provided to illustrate the invention and are not intended to limit the invention in any way.

[0364] Example B1: Corynebacterium multiflorum (Target leaf spot disease) - Liquid culture assay

[0365] The compound through in vitro Test targeting Corynebacterium multiflorum Screening is performed. Active ingredients are compared with... Corynebacterium multiflorumThe spores were integrated together with liquid medium in 96-well plates at a series of different ratios. After incubation, mycelial growth in the wells was assessed and scored as a percentage control relative to untreated wells. These scores for different concentrations of the compound in the liquid medium are shown in the table below, together with a comparison with the individual active ingredients from commercial standards used in field trials (Table 1).

[0366] Table 1: Results, for Corynebacterium multiflorum Liquid culture assays for (target leaf spot disease)

[0367]

[0368] Example B2: Corynebacterium multiflorum (Target leaf spot disease) - Field trial 2022 / 2023

[0369] Various compounds were formulated and applied to soybean plants using a handheld horizontal boom sprayer via foliar spraying. Three applications were made during the growing season, beginning approximately 45 days after crop emergence, followed by applications at approximately 14-day intervals. Trials were conducted at five sites in Brazil.

[0370] At approximately weekly intervals, based on the percentage of leaf area covered by disease lesions, [the following is a separate, unrelated sentence:] [The text appears to be incomplete and requires further context.] Corynebacterium multiflorum Infection severity was assessed. Results showing disease reduction in treated plots relative to untreated plots are presented (Table 2a is for the 2023 season and Table 2b is for the 2024 season). Values ​​for untreated plots represent % severity.

[0371] The improved yield is calculated by subtracting the yield of the untreated plants from the yield of the treated plants, then dividing the result by the absolute value of the untreated plant yield and multiplying the result by 100. The answer is a percentage increase.

[0372] Table 2a: Results, for Corynebacterium multiflorum Field trials of target leaf spot disease - 2023 season

[0373]

[0374] Table 2b: Results, for Corynebacterium multiflorum Field trials of target leaf spot disease - Season 2024

[0375]

[0376] na means the result is unavailable

[0377] When compared with an untreated control that showed extensive disease development under the same conditions, these compounds (IA) and (IB) gave approximately 50% control.

[0378] Given the lack of activity against the same fungi in liquid culture, especially when compared to the relative activity of the active ingredient from commercial products in liquid culture, the compound's field performance is questionable. Corynebacterium multiflorum The activity—providing overall control similar to that of commercial ternary mixtures—is unexpected and surprising.

[0379] Therefore, compounds having formula (I), (IA), or (IB) may be distinguished from other compounds, for example, by their greater efficacy at lower application rates, which can be demonstrated by those skilled in the art using the experimental procedures outlined in the above biological tests, with lower application rates (if necessary), such as 6 ppm, 3 ppm, 2.2 ppm, 1.5 ppm, 0.8 ppm, or 0.74 ppm.

Claims

1. A method for controlling or preventing plant infection by the plant pathogenic microorganism *Cercospora multiflora*, the method comprising applying to the plant pathogen, the site of the plant pathogen, or a plant susceptible to the plant pathogen, or its propagation material a compound of formula (I) or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof. (I) in R 1 Selected from C1-C4-alkyl, C1-C2-haloalkyl, C1-C2-alkoxy, C3-C6-cycloalkyl, or C1-C2-alkoxy-C1-C3-alkyl; R 2 Selected from hydrogen or C1-C2-alkoxy groups; R 3 R 4 Independently selected from hydrogen or C1-C4-alkyl; and R 5 Selected from C1-C2-halogenated alkyl groups.

2. A method for controlling or preventing plant infection by the plant pathogenic microorganism *Cercospora multiflora*, the method comprising applying a pest-killing composition to the plant pathogen, the site of the plant pathogen, or a plant susceptible to the plant pathogen, or its propagation material, the pest-killing composition comprising a compound having formula (I) as defined in claim 1 and one or more adjuvants.

3. The method according to claim 1 or 2, wherein, Apply the compound or composition in the field.

4. The method according to any one of claims 1 to 3, wherein, The compound or composition is applied by foliar application, soil application, furrow application, or irrigation.

5. The method according to any one of claims 1 to 4, wherein, The compound according to formula (I) is applied at a rate of at least 10 g / ha, preferably at least 10, 15, 20, 25, 30, 35, or 40 g / ha.

6. The method according to any one of claims 1 to 5, wherein, The compound according to formula (I) is applied at a rate of up to 80 g / ha, preferably up to 80, 75, 70, 65, 60, 55, 50 or 45 g / ha.

7. The method according to any one of claims 1 to 6, wherein, The compound according to formula (I) is selected from N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide (a compound having formula (IA); or (I-A) N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acrylamide (a compound having formula (IB)) (I-B)。 8. The method according to any one of claims 1 to 7, wherein, The compound according to formula (I) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide (a compound having formula (IA)).

9. A method for controlling or preventing plant infection by the plant pathogenic microorganism *Cercospora multiflora*, the method comprising applying a compound having formula (I) as defined in any one of claims 1, 7 or 8 and one or more pest control agents as a mixture to the plant pathogen, the site of the plant pathogen, or a plant susceptible to the plant pathogen, or its propagation material.

10. The method according to any one of claims 1 to 9, wherein, The plants are selected from soybeans, corn, wheat, cotton, legumes, potatoes, sweet potatoes, and tobacco.

11. The method according to any one of claims 1 to 10, wherein, The plant is a genetically modified plant selected from soybean, corn, wheat, cotton, legumes, potato, sweet potato, and tobacco.

12. The method according to any one of claims 1 to 11, wherein, The plant in question is a Bt plant.

13. The method according to any one of claims 1 to 12, wherein, The plant is selected from soybeans or cotton, preferably soybeans.

14. The method according to any one of claims 1 to 13, the method comprising the following steps: Provide a composition comprising a biocidally effective amount of a compound having formula (I); And the application of the composition to reproductive material; And planting the propagation material, preferably in the field.

15. The method according to any one of claims 1 to 14, the method comprising the following steps: Provide a composition comprising a biocidally effective amount of a compound having formula (I); and apply the composition to the plant pathogen, the site of the plant pathogen, or a plant susceptible to the plant pathogen.

16. Use of a compound of formula (I) as defined in any one of claims 1, 7 or 8 for controlling *Cercospora multiflora* in genetically modified soybean, cotton or maize by the method according to any one of claims 1 to 15.

Images