Bactericidal mixture containing pyrazole derivatives

Abstract

The present invention provides a fungicidal composition used to protect plants or plant seeds from diseases caused by specific fungal pathogens. [Solution] A bactericidal composition is provided, comprising a compound of the following formula and an additional bactericidal compound. TIFF2026048856000073.tif4988

Description

[Technical Field]

[0001] The present invention relates to specific pyrazoles, their N-oxides, salts, and mixtures and compositions comprising such halomethyl ketones and hydrate derivatives, and to methods for using such halomethyl ketones and hydrate derivatives, as well as mixtures and compositions thereof, as bactericides. [Background technology]

[0002] Controlling plant diseases caused by fungal plant pathogens is crucial for achieving high crop efficiency. Plant disease damage to ornamental plants, vegetables, field crops, grains, and fruit crops can lead to significant reductions in productivity, thereby increasing costs for consumers. In addition to often being highly destructive, plant diseases can be difficult to control and can develop resistance to commercially available fungicides. For these purposes, many products are available on the market, but there is still a need for novel fungicides that are more effective, less expensive, less toxic, more environmentally safe, or have different sites of action. In addition to introducing novel fungicides, combinations of fungicides are often used to promote disease control, broaden the spectrum of control, and slow the development of resistance. Furthermore, certain unusual combinations of fungicides demonstrate effects greater than additive (i.e., synergistic) to provide a commercially significant level of plant disease control. In the art, it is recognized that the advantages of a particular combination of fungicides vary depending on factors such as the specific plant species and the plant disease being treated, and regardless of whether the plant is treated before or after infection by a fungal plant pathogen. Therefore, there is a need for novel advantageous combinations to provide a variety of options to best meet specific plant disease control requirements. Here, such a combination has been discovered.

[0003] PCT Patent Publication International Publication Nos. 2018 / 052838, 2013 / 192126, 2012 / 031061, and 2010 / 101973 disclose fungicidal pyrazoles and their use in agriculture. PCT Patent Publication International Publication No. 2019 / 020981 discloses pyrazoles, isothiazoles, and isoxazole derivatives and their use in agriculture. [Overview of the project] [Means for solving the problem]

[0004] The present invention relates to a bactericidal composition (i.e., a combination), (a) Formula 1: [ka] (In the formula, R 1 These are C1-C2 alkyl groups, R 2 These are cyano, halogen, C1-C2 alkyl, or C1-C2 haloalkyl, R 3 is a halogen or methyl, Each R 4 These are independently halogen, cyano, nitro, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C2-C6 cyanoalkoxy, C2-C6 alkoxyalkyl, or C2-C6 alkoxyalkoxy. Each R 5 These are independently halogens, C1-C3 alkyls, C2-C6 alkoxyalkyls, C1-C3 alkoxys, C1-C3 haloalkoxys, C2-C6 alkenyloxys, C2-C6 alkynyloxys, C2-C6 cyanoalkoxys, or C2-C6 alkoxyalkoxys. m and n are independently 0, 1, 2, or 3. R 6 is H; or R6a C1-C3 alkyl or C1-C3 haloalkyl, each optionally substituted with up to two substituents independently selected therefrom; or amino, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CH(=O), S(=O)2OM, S(=O) u R 7 , (C=W)R 8 or OR 9 wherein each R 6a is independently cyano, C3-C6 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl, M is K or Na, u is 0, 1 or 2, R 7 is C1-C3 alkyl or C1-C3 haloalkyl, W is O or S, R 8 is C1-C3 alkyl, C2-C4 alkoxyalkyl, C2-C4 alkylaminoalkyl, C3-C6 dialkylaminoalkyl, C1-C3 alkoxy, C1-C3 alkylthio or C2-C4 alkylthioalkyl, R 9 is H; or R 9a is C1-C3 alkyl or C1-C3 haloalkyl, each optionally substituted with up to two substituents independently selected therefrom; or CH(=O), C3-C6 cycloalkyl, S(=O)2OM or (C=W)R 10 wherein each R 9a is independently cyano, C3-C6 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl, and R 10(These are C1-C3 alkyl, C2-C4 alkoxyalkyl, C2-C4 alkylaminoalkyl, C3-C6 dialkylaminoalkyl, C1-C3 alkoxy, C1-C3 alkylthio, or C2-C4 alkylthioalkyl.) A compound (including all stereoisomers), at least one compound selected from its N-oxide and salt, (b) at least one additional bactericidal compound and This includes, however, the compound of formula 1 is 4-(2,6-difluoro-4-methoxyphenyl)-N-(2,4-difluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-N-(2-nitrophenyl)-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2,4-difluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-3-ethyl-1-methyl-N-(2-nitrophenyl)-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-1-methyl-N-(2-nitrophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-amine, 4-(2,6-difluoro-4-methoxyphenyl)-N-(2-methoxy-6-nitro Phenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-methoxy-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, N-(2-chloro-6-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazole-5-amine, N-(2-chloro-3-fluoro-6-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-N-(2-methyl-6-nitrophenyl)-1H-pyrazole-5-amine, N-(2-bromo-4-fluoro-6-nitrophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(4-methoxy-2-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2,6-difluoro-4-methoxyphenyl)-N-(4-fluoro-2-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2,6-difluoro-4-methoxyphenyl)-N-(4-methoxy-2-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, N-(4-chloro-2-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-N-[2-nitro-4-(2-propyne-1-yloxy)phenyl]-1H-pyrazole-5-amine, 4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-N-[2-nitro-4-(2-propene-1-yloxy)phenyl]-1H-pyrazole-5-amine, N-(4-bromo-2-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazole-5-amine, N-(4-chloro-2-fluoro-6-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 3-Chloro-4-(2-chloro-4-fluorophenyl)-N-(2,4-difluoro-6-nitrophenyl)-1-methyl-1H-pyrazole-5-amine, 4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-N-[4-methyl-2-nitrophenyl]-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-N-(4-methyl-2-nitrophenyl)-1H-pyrazole-5-amine, and N-(4-bromo-2-fluoro-6-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazole-5-amine This relates to bactericidal compositions (i.e., combinations) provided that they are not [the specified condition].

[0005] The present invention also relates to (a) a composition comprising at least one compound selected from the compound of Formula 1, its N-oxide and salt, and at least one invertebrate pest control compound or agent.

[0006] The present invention also relates to a composition comprising one of the compositions, which comprises component (a) and at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents.

[0007] The present invention also relates to a method for controlling plant diseases caused by fungal plant pathogens, comprising applying one fungicidal effective amount of the composition to a plant or a part thereof or to the seeds of a plant.

[0008] The method described above may also be described as a method for protecting a plant or plant seed from diseases caused by fungal plant pathogens, comprising applying one fungicidal effective amount of the composition to the plant (or a part thereof) or plant seed (directly or through the environment of the plant or plant seed (e.g., a growing medium)).

[0009] The present invention also relates to the compound of formula 1 described above, or its N-oxide or salt. [Modes for carrying out the invention]

[0010] As used herein, the terms “include,” “contain,” “encompass,” “incorporate,” “have,” “possess,” “contain,” “contain,” and “characterize,” or any variation thereof, are intended to include non-exclusive inclusion subject to any expressly indicated limitations. For example, a composition, mixture, process, method, article, or apparatus containing a list of elements is not necessarily limited to those elements alone and may also include other elements that are not expressly enumerated or that are inherent to such composition, mixture, process, method, article, or apparatus.

[0011] The transitional phrase "consisting of" excludes any unspecified element, step, or component. In a claim, it is usually associated with the claim if the claim is closed in a way that it includes a substance different from those cited, apart from impurities. If the phrase "consisting of" appears in a clause of the main part of a claim rather than immediately following the preamble, it limits only the elements mentioned in that clause, and other elements are not excluded from the claim as a whole.

[0012] The transitional phrase “substantially from” is used to define a composition, method, or apparatus that includes substances, steps, features, components, or elements in addition to those literally disclosed, provided that these additional substances, steps, features, components, or elements do not substantially affect the fundamental and novel characteristics of the claimed invention. The term “substantially from” occupies an intermediate position between “includes” and “consists of.”

[0013] If the applicant defines the present invention or a part thereof using open-ended terms such as "including," it should be readily understood that such descriptions should also be interpreted as describing such inventions using terms such as "substantially consisting of" or "consisting of" (unless otherwise stated).

[0014] Furthermore, conversely, unless explicitly stated otherwise, "or" refers to an inclusive "or" and not an exclusive "or". For example, the condition "A or B" is satisfied by any one of the following: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), and both A and B are true (or exist).

[0015] Furthermore, the indefinite articles “a” and “an” preceding an element or component of the present invention are not restrictive with respect to the number of cases (i.e., occurrences) of that element or component. Thus, “a” and “an” should be read as including one or at least one, and also including plurals unless it is clear from such singular form of the element or component that the number means singular.

[0016] The term "agriculture" refers to the production of agricultural products such as food and fiber, including maize or corn, soybeans and other legumes, rice, grains (e.g., wheat, oats, barley, rye and rice), leafy vegetables (e.g., lettuce, cabbage and other vegetable crops), fruit vegetables (e.g., tomatoes, peppers, eggplants, crucifers and cucurbits). This includes the cultivation of potatoes, sweet potatoes, grapes, cotton, fruit trees (e.g., pears, drupes, and citrus fruits), small fruit trees (e.g., berries and cherries), and other specialty crops (e.g., canola, sunflowers, and olives).

[0017] The term "non-agricultural" refers to anything other than agricultural crops, including horticultural crops (e.g., ornamental plants that do not grow in greenhouses, nurseries, or fields), residential, agricultural, commercial and industrial structures, turf (e.g., turf farms, pastures, golf courses, lawns, sports fields, etc.), wood products, storage products, afforestation and vegetation management, and public health (i.e., human) and animal health (e.g., domesticated animals such as pets, livestock and poultry, and undomesticated animals such as wildlife).

[0018] The term "crop vitality" refers to the rate of growth or biomass deposition of crop plants. "Increased vitality" refers to the increase in growth or biomass deposition in crop plants compared to untreated control crop plants. The term "crop yield" refers to the yield of crop material, both in terms of quantity and quality, obtained after harvesting crop plants. "Increased crop yield" refers to the increase in crop yield compared to untreated control crop plants.

[0019] The term "biologically effective amount" refers to the amount of a bioactive compound (e.g., a compound of Formula 1) sufficient to produce a desired biological effect when applied (i.e., in contact) to the fungus being controlled or its environment or the plant, the seed or the plant's location (e.g., the growing medium) for the purpose of protecting the plant from damage caused by fungal diseases or for other desired effects (e.g., increased plant vitality).

[0020] Where referenced in this disclosure and claims, “plant” includes members of the Kingdom Plantae at all life stages, including seedlings (e.g., germinating seeds that develop into seedlings) and mature, reproductive growth stages (e.g., plants that produce flowers and seeds), in particular seed plants (Spermatopsida). Parts of a plant include geotropic members that typically grow below the surface of the growth medium (e.g., soil), such as rhizomes, tubers, bulbs and corms, and above the surface of the growth medium (e.g., soil), such as leaves (including stems and leaves), flowers, fruits and seeds.

[0021] Where used herein, the term “seedling,” whether alone or in combination with other words, means a young plant developing from the embryo of a seed.

[0022] Where used herein, the term “broadleaf” either alone or in a term such as “broadleaf crops” means dicotyledonous or dicotyledonous plants, and the term is used to describe a group of angiosperms characterized by an embryo having two cotyledons.

[0023] Where referenced in this disclosure, the terms “fungal pathogens” and “fungal plant pathogens” include pathogens of the Ascomycota, Basidiomycota, and Zygomycota phyla, as well as fungal-like Oomycota species, which are causative pathogens of a broad spectrum of plant diseases affecting economically important ornamental plants, turfs, vegetables, fields, grains, and fruit crops. In relation to this disclosure, “protecting plants from disease” or “controlling plant diseases” includes preventive action (disruption of the fungal cycle of infection, colonization, symptom development, and spore formation) and / or therapeutic action (inhibition of colonization of plant host tissues).

[0024] As used herein, the term “Mechanism of Action” (MOA) is as defined by the Fungicide Resistance Action Committee (FRAC) and is used to identify fungicides by their biochemical mechanism of action in the biosynthetic pathway of plant pathogens and their resistance risk. The mechanisms of action as defined by the FRAC are: (A) nucleic acid metabolism, (B) cytoskeleton and motor proteins, (C) respiration, (D) amino acid and protein synthesis, (E) signal transduction, ( F) Lipid synthesis or transport and membrane integrity or function, (G) Membrane sterol biosynthesis, (H) Cell wall biosynthesis, (I) Cell wall melanin synthesis, (P) Host plant defense induction, (U) Unknown mechanism of action, (M) Chemicals with multi-site activity, and (BM) Biologics with multiple mechanisms of action. Each mechanism of action (i.e., letters A-BM) contains one or more subgroups based on individual confirmed target sites of action, or, if the exact target site is unknown, based on cross-resistance profiles within or with other groups (e.g., A includes subgroups A1, A2, A3, and A4). Each of these subgroups (e.g., A1, A2, A3, and A4) is assigned a FRAC code (number and / or letter). For example, the FRAC code for subgroup A1 is 4. Additional information on target sites and FRAC codes can be obtained, for example, from publicly available databases by FRAC.

[0025] As used herein, the term “cross-resistance” refers to the phenomenon that occurs when a pathogen develops resistance to one fungicide and simultaneously becomes resistant to one or more other fungicides. These other fungicides are, but not always, typically of the same chemical classification, have the same target site of action, or can be detoxified by the same mechanism.

[0026] In general, when a molecular fragment (i.e., a group) is represented by a series of atomic symbols (e.g., C, H, N, O, and S), the implicit attachment point is readily apparent to those skilled in the art. In this specification, the attachment point may be explicitly indicated by a hyphen ("-"), as is sometimes the case, particularly when an alternative attachment point is possible. For example, "-NCS" indicates that the attachment point is a nitrogen atom (i.e., isothiocyanate, not thiocyanate).

[0027] As used herein, the term "alkylating agent" refers to a compound in which a carbon-containing group is bonded to a leaving group, such as a halide or sulfonate, via a carbon atom (which can be substituted by bonding a nucleophile to the carbon atom). Unless otherwise indicated, the term "alkylation" is not limited to alkyl groups, and the carbon-containing group in an alkylating agent may be, for example, R 5 It includes various carbon bond substituents identified for this purpose.

[0028] In the above description, the term "alkyl," used alone or in compound terms such as "alkylthio" or "haloalkyl," includes linear or branched alkyl groups, e.g., methyl, ethyl, n-propyl, and i-propyl or various butyl, pentyl, or hexyl isomers. "Alkenyl" includes linear or branched alkenes, e.g., ethenyl, 1-propenyl, 2-propenyl, and various butenyl, pentenyl, and hexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes linear or branched alkynes, e.g., 1-propynyl, 2-propynyl, and various butynyl, pentynyl, and hexynyl isomers. "Alkynyl" may also include moieties consisting of multiple triple bonds, e.g., 2,5-hexadienyl.

[0029] "Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, i-propyloxy, and different butoxy, pentoxy, and hexyloxy isomers. "Alkoxyalkyl" indicates alkoxy substitution on an alkyl group. Examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2, and CH3CH2OCH2CH2. "Alkenyloxy" includes linear or branched alkenyls that are attached to an oxygen atom and linked via the oxygen atom. Examples of "alkenyloxy" include H2C=CHCH2O, (CH3)2C=CHCH2O, CH3CH=CHCH2O, CH3CH=C(CH3)CH2O, and CH2=CHCH2CH2O. "Alkynyloxy" indicates that the alkoxy substitution on an alkyl group is attached to an oxygen atom and linked via the oxygen atom. This includes linear or branched alkynyls linked via their children. Examples of "alkynyloxy" include HC≡CCH2O, CH3C≡CCH2O, and CH3C≡CCH2CH2O. "Alkoxyalkoxy" indicates an alkoxy substitution on another alkoxy moiety. Examples of "Alkoxyalkoxy" include CH3OCH2O, CH3OCH2O, and CH3CH2OCH2O.

[0030] "Alkylthio" includes branched or linear alkylthio moieties, such as methylthio, ethylthio, and different propylthio isomers. "Alkylthioalkyl" indicates alkylthio substitution on an alkyl group. Examples of "Alkylthioalkyl" include CH3SCH2, CH3SCH2CH2, CH3CH2SCH2, and CH3CH2SCH2CH2. "Alkylsulfinyl" includes both enantiomers of the alkylsulfinyl group. Examples of "Alkylsulfinyl" include CH3S(=O), CH3CH2S(=O), CH3CH2CH2S(=O), and (CH3)2CHS(=O). Examples of "Alkylsulfonyl" include CH3S(=O)2, CH3CH2S(=O)2, CH3CH2CH2S(=O)2, and (CH3)2CHS(=O)2.

[0031] "Alkylaminoalkyl" indicates alkylamino substitution on an alkyl group. Examples of "alkylaminoalkyl" include CH3NHCH2, CH3NHCH2CH2, CH3CH2NHCH2, CH3CH2CH2CH2NHCH2, and CH3CH2NHCH2CH2. Examples of "dialkylaminoalkyl" include (CH3)2NCH2, (CH3CH2)2NCH2CH2, and CH3CH2(CH3)NCH2CH2.

[0032] The term "cycloalkyl" refers to a saturated carbocyclic ring consisting of 3 to 6 carbon atoms linked to each other by single bonds. Examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The term "cycloalkylalkyl" refers to a cycloalkyl substitution on an alkyl group. Examples of "cycloalkylalkyl" include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to linear or branched alkyl groups.

[0033] The term "halogen" includes fluorine, chlorine, bromine, or iodine when used alone, within a compound term such as "haloalkyl," or in a description such as "halogen-substituted alkyl." Furthermore, when used in a compound term such as "haloalkyl" or in a description such as "halogen-substituted alkyl," the alkyl may be partially or completely substituted with the same or different halogen atoms. Examples of "haloalkyl" or "halogen-substituted alkyl" include F3C, ClCH2, CF3CH2, and CF3CCl2. The term "haloalkoxy," etc., is defined similarly to the term "haloalkyl." Examples of "haloalkoxy" include CF3O, CCl3CH2O, F2CHCH2CH2O, and CF3CH2O.

[0034] "Cyanolalkoxy" refers to an alkyloxy group substituted with one cyano group. Examples of "cyanoalkoxy" include NCCH2O, NCCH2CH2O, and CH3CH(CN)CH2O.

[0035] The total number of carbon atoms in the substituent is the prefix "C i ~C j These are represented by , where i and j are numbers from 1 to 6. For example, C1-C3 alkylsulfonyls represent methylsulfonyl to propylsulfonyl, C2 alkoxyalkyls represent CH3OCH2, C3 alkoxyalkyls represent, for example, CH3OCH2CH2 or CH3CH2OCH2, and C4 alkoxyalkyls represent various isomers of alkyl groups substituted with alkoxy groups containing a total of four carbon atoms, examples of which include CH3CH2CH2OCH2 and CH3CH2OCH2CH2.

[0036] The term “unsubstituted” in relation to rings and other groups means that the group has no substituents other than its one or more bonds to the remainder of Formula 1. The term “optionally substituted” means that the number of substituents can be zero. Unless otherwise specified, an optionally substituted group can be substituted with as many optional substituents as possible, which are applied by substituting a hydrogen atom with a non-hydrogen substituent on any available carbon or nitrogen atom. Generally, the number of optional substituents (if any) ranges from 1 to 3. As used herein, the term “optionally substituted” is interchangeable with the phrases “substituted or unsubstituted” or the term “(un)substituted.”

[0037] The number of optional substituents can be limited by the expressed limit. For example, the phrase "R 6a "Optionally substituted with up to two substituents independently selected from " means that there may be 0, 1, or 2 substituents.

[0038] A substituent having a subscript indicating that the number of substituents is variable (for example, (R) of formula 1 where m is 0 to 3) 4 ) m When a compound is substituted by a substituent, unless otherwise specified, the substituent is selected independently from the defined group of substituents. When it is indicated that various groups are arbitrarily linked at a certain position (for example, m may be 0 (R 4 ) m ), even if not explicitly stated in the definitions of various groups, hydrogen can be present in that position.

[0039] The naming of substituents in this disclosure uses accepted terminology that is concise in accurately conveying the chemical structure to those skilled in the art. For the sake of brevity, locanto descriptive terms may be omitted. In this specification, substituents (e.g., R) may be used as appropriate. 4 and R 5 The attachment points of ) are indicated by locant numbers, which may differ from the naming system of Chemical Abstracts if the difference does not affect the meaning.

[0040] The compounds of the present invention may have one or more stereoisomers. Stereoiomers are isomers that have the same composition but differ in the spatial arrangement of their atoms, and include enantiomers, diastereomers, cis- and trans-isomers (also known as geometric isomers), and atropisomers. Atropisomers arise from binding rotation around a single bond, and because the barrier to this rotation is high, it is possible to isolate the isomer species. Those skilled in the art will understand that when one stereoisomer is at a higher concentration than other stereoisomers or when it is separated from other stereoisomers, it may exhibit higher reactivity and / or a more favorable effect. In addition, those skilled in the art will know methods for separating, enriching, and / or selectively preparing such stereoisomers. For a comprehensive discussion of all aspects of stereoisomerism, see the following document: Ernest L. Eliel and Samuel H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, 1994.

[0041] The compounds of the present invention may also exist as one or more conformational isomers due to binding rotation around the amide bond (e.g., C(=O)-N) in Formula 1. The present invention also includes mixtures of conformational isomers. In addition, the present invention also includes compounds enriched with one conformational isomer relative to the other.

[0042] This invention includes all stereoisomers, structural isomers, mixtures thereof in all proportions, and isotope forms such as deuterated compounds.

[0043] Those skilled in the art will know that not all nitrogen-containing heterocycles can form N-oxides because the nitrogen requires an available lone pair of electrons to be oxidized to an oxide. Those skilled in the art will understand that this is the case. Those skilled in the art will recognize that the nitrogen-containing heterocycle can form an N-oxide. Those skilled in the art will also recognize that tertiary amines can form an N-oxide. Synthetic methods for preparing N-oxides of heterocycles and tertiary amines will be well known to those skilled in the art, including oxidizing heterocycles and tertiary amines with peroxy acids, such as peracetic acid and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides, such as t-butyl hydroperoxide, sodium perborate, and dioxiranes, such as dimethyldioxiran. These methods for preparing N-oxides are widely described and reviewed in the literature; see, for example, the following: TLGilchrist, Comprehensive Organic Synthesis, vol.7, pp 748-750 (SVLey, Ed., Pergamon Press); M.Tisler and B.Stanovnik, Comprehensive Heterocyclic Chemistry, vol.3, pp.18-20, AJBoulton and A.McKillop, Eds., Pergamon Press; MRGrimmett and BRTKeene, Advances in Heterocyclic Chemistry, vol.43, pp.149-161, ARKatritzky, Ed., Academic Press; M.Tisler and B.Stanovnik, Advances in Heterocyclic Chemistry, vol.9, pp.285-291, ARKatritzky and AJBoulton, Eds., Academic Press; and GWHCheeseman and ESGWerstiuk, Advances in Heterocyclic Chemistry, vol. 22, pp. 390-392, ARKatritzky and AJ Boulton, Eds., Academic Press.

[0044] As those skilled in the art recognize, under environmental and physiological conditions, salts of compounds are in equilibrium with their corresponding unsalted forms, and therefore salts share biological utility with their unsalted forms. Consequently, a wide variety of salts of compounds of formula 1 are useful (i.e., suitable as pesticides) for controlling plant diseases caused by fungal plant pathogens. Examples of salts of compounds of formula 1 include acid addition salts with inorganic or organic acids such as: hydrobromic acid, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetic acid, butyric acid, fumaric acid, lactic acid, maleic acid, malonic acid, oxalic acid, propic acid, salicylic acid, tartaric acid, 4-toluenesulfonic acid, or valeric acid. When a compound of formula 1 contains an acidic residue such as a carboxylic acid, the salt also includes, for example, those formed using an organic or inorganic base, such as: pyridine, triethylamine, or ammonia or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium, or barium. Therefore, the present invention comprises compounds selected from Formula 1, their N-oxides, and salts suitable as pesticides.

[0045] Compounds selected from Formula 1, their stereoisomers, N-oxides, and salts typically exist in two or more forms; therefore, Formula 1 encompasses all crystalline and amorphous forms of the compounds represented by Formula 1. Amorphous forms include solid embodiments, e.g., waxes and rubbers, and liquid embodiments, e.g., solutions and melts. Crystalline forms include embodiments representing substantially single-crystal types and embodiments representing mixtures of polymorphs (i.e., multiple crystalline types). The term "polymorph" refers to a particular crystalline form of a compound that can crystallize in various crystalline forms, and these forms have various arrangements and / or conformations of molecules in the crystal lattice. Multiple polymorphs may have the same chemical composition, but they may also differ in composition depending on the presence or absence of co-crystallized water or other molecules that may be weakly or strongly bonded in their lattice. Polymorphs may differ in terms of chemical, physical, and biological properties such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspension, dissolution rate, and biological availability. Those skilled in the art will see that certain polymorphs of a compound represented by formula 1 are determined by formula 1. It will be understood that, compared to other polymorphs or mixtures of polymorphs of the same compound represented, it may exhibit advantageous effects (e.g., suitability for preparing useful formulations, improved biological performance). The preparation and isolation of specific polymorphs of the compound represented by Formula 1 can be achieved by methods known to those skilled in the art, such as crystallization using a selected solvent and temperature.

[0046] As described in the summary of the present invention, aspects of the present invention relate to compositions comprising (a) at least one compound selected from Formula 1, its N-oxide and salt, and (b) at least one additional bactericidal compound. More particularly, component (b) is (b1) Methylbenzimidazole carbamate (MBC) fungicide, (b2) Dicarboxyimide fungicide, (b3) Demethylation inhibitor (DMI) bactericides, (b4) Phenylamide (PA) fungicide, (b5) Amine / morpholine fungicides, (b6) Phospholipid biosynthesis inhibitors, bactericides, (b7) Succinate dehydrogenase inhibitors (SDHI) bactericides, (b8) Hydroxy(2-amino-)pyrimidine fungicide, (b9) Anilinopyrimidine (AP) fungicide, (b10) N-phenylcarbamate fungicide, (b11) Quinone outside inhibitor (QoI) bactericides, (b12) Phenylpyrrole (PP) fungicide, (b13) Azanafthene fungicide, (b14) Cell peroxidation inhibitor bactericides, (b15) Melanin biosynthesis inhibitor-reductase (MBI-R) bactericide, (b16a) Melanin biosynthesis inhibitor - dehydratase (MBI-D) bactericide, (b16b) Melanin biosynthesis inhibitor - polyketide synthase (MBI-P) bactericide, (b17) Ketoreductase inhibitors (KRIs) bactericides, (b18) Squalene epoxidase inhibitor bactericide, (b19) Polyoxin disinfectant, (b20) Phenylurea fungicide, (b21) Quinone inside inhibitor (QiI) bactericide, (b22) Benzamide and thiazole carboxamide fungicides, (b23) Enopyranuronic acid antibiotic fungicide, (b24) Hexopyranocil antibiotic fungicide, (b25) Glucopyranosyl antibiotics: protein synthesis bactericides, (b26) Glucopyranosyl antibiotic bactericide, (b27) Cyanoacetamido oxime fungicide, (b28) Carbamate fungicides, (b29) Oxidative phosphorylation uncoupling bactericides, (b30) Organotin fungicides, (b31) Carboxylic acid fungicide, (b32) Heterocyclic aromatic compound fungicides, (b33) Phosphonate fungicides, (b34) Phthalamide acid fungicide, (b35) Benzotriazine fungicide, (b36) Benzene sulfonamide fungicide, (b37) Pyridazinone fungicide, (b38) Thiofen-carboxamide fungicide, (b39) Complex I NADH oxidoreductase inhibitor bactericide, (b40) Carboxylate amide (CAA) fungicides, (b41) Tetracycline antibiotics and fungicides, (b42) Thiocarbamate fungicides, (b43) Benzamide fungicide, (b44) Microbial disinfectants, (b45) Quinone outside inhibitors, stigmatelin-conjugated (QoSI) bactericides, (b46) Plant extract fungicide, (b47) Cyanoacrylate fungicide, (b48) Polyene fungicides, (b49) Oxysterol-binding protein inhibitors (OSBPIs) bactericides, (b50) Arylphenyl ketone fungicide, (b51) Host plant defense-inducing fungicides, (b52) Multi-site active fungicide, (b53) Biological agents having multiple mechanisms of action, (b54) Bactericides other than those of component (a) and components (b1) to (b53), and salts of compounds (b1) to (b54) It is selected from the group consisting of the following.

[0047] Embodiments in which component (b) comprises at least one bactericidal compound from each of two different groups selected from (b1) to (b54) are noted.

[0048] Methylbenzimidazole carbamate (MBC) bactericides (b1) (FRAC code 1) inhibit mitosis by binding to β-tubulin during microtubule association. Inhibition of microtubule association can disrupt cell division, intracellular transport, and cellular structure. Methylbenzimidazole carbamate bactericides include benzimidazole and thiophanate bactericides. Benzimidazoles include benomyl, carbendazim, fuberidazole, and thiabendazole. Thiophanates include thiophanate and thiophanate-methyl.

[0049] Dicarboximide fungicides (b2) (FRAC code 2) inhibit mitogen-activated protein (MAP) / histidine kinase in osmotic signaling. Examples include clozolinates, dimethacron, iprodione, procymidone, and vinclozoline.

[0050] Demethylation inhibitor (DMI) fungicides (b3) (FRAC code 3) (sterol biosynthesis inhibitors (SBI): class I) inhibit C14 demethylase, which is involved in sterol production. Sterols, such as ergosterol, are required for membrane structure and function, and are therefore essential for the development of functional cell walls. Consequently, exposure to these fungicides leads to abnormal growth and ultimately death of susceptible fungi. DMI fungicides are divided into several chemical classes: piperazines, pyridines, pyrimidines, imidazoles, triazoles, and triazolinthions. Piperazines include triforine. Pyridines include butiobate, pyrifenox, pyrisoxazole, and (αS)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-4-isoxazolyl]-3-pyridineemethanol. Pyrimidines include phenalimol, nualimol, and trialimol. Imidazoles include econazole, imazalil, oxpoconazole, pefurazoate, prochloraz, and triflumizole. Triazoles include azaconazole, vitertanol, bromconazole, cyproconazole, difenoconazole, diniconazole (including diniconazole-M), epoxyconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafole, hexaconazole, imibenconazole, ipconazole, ipfentrifluconazole, mefentrifluconazole, metconazole, mycrobutanil, penconazole Zole, propiconazole, quinconazole, simeconazole, tebuconazole, tetraconazole, triadimephon, triadimenol, triticonazole, uniconazole, uniconazole-P, α-(1-chlorocyclopropyl)-α-[2-(2,2-dichlorocyclopropyl)ethyl]-1H-1,2,4-triazole-1-ethanol, rel-1-[[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-2-oxylani It contains triazole-methyl-1H-1,2,4-triazole, rel-2-[[(2R,3S)-3-(2-chlorophenyl)-2(2,4-difluorophenyl)-2-oxyranyl]methyl]-1,2-dihydro-3H-1,2,4-triazole-3-thione, and rel-1-[[(2R,3S)-3-(2-chlorophenyl)-2(2,4-difluorophenyl)-2-oxyranyl]methyl]-5-(2-propene-1-ylthio)-1H-1,2,4-triazole. Triazolinthione contains prothioconazole. Biochemical investigations have revealed that all of the above fungicides are DMI fungicides described by KHKuck et al. in Modern Selective Fungicides - Properties, Applications and Mechanisms of Action, H. Lyr (Ed.), Gustav Fischer Verlag: New York, 1995, 205-258.

[0051] Phenylamide (PA) fungicides (b4) (FRAC code 4) are specific inhibitors of RNA polymerase in Oomycete fungi. Susceptible fungi exposed to these fungicides show a reduced ability to incorporate uridine into rRNA. Exposure to this class of fungicides inhibits the growth and development of susceptible fungi. Phenylamide fungicides include acylalanine, oxazolidinone, and butyrolactone fungicides. Acylalanine includes venalaxyl, venalaxyl-M (also known as quilaraxyl), flaxyl, metalaxyl, and metalaxyl-M (also known as mephenoxam). Oxazolidinone includes oxadixyl. Butyrolactone includes offrace.

[0052] "Amine / morpholine fungicide (b5)" (FRAC code 5) (SBI: class II) targets two sites in the sterol biosynthesis pathway, Δ 8 →Δ 7 isomerase and Δ 14 They inhibit reductase. Sterols, such as ergosterol, are required for membrane structure and function, and are therefore essential for the development of functional cell walls. Consequently, exposure to these fungicides leads to abnormal growth and ultimately death of susceptible fungi. Amine / morpholine fungicides (also known as non-DMI sterol biosynthesis inhibitors) include morpholine, piperidine, and spirochetal-amine fungicides. Morpholine includes algimorph, dodemorph, fenpropimorph, tridemorph, and trimorphamide. Piperidine includes fenpropidine and piperaline. Spirochetal amines include spiroxamine.

[0053] Phospholipid biosynthesis inhibitor fungicides (b6) (FRAC code 6) inhibit the growth of fungi by affecting phospholipid biosynthesis. Phospholipid biosynthesis inhibitor fungicides include phosphorothiolate fungicides and dithiolane fungicides. Phosphothiolates include edifenfos, ipropenfos, and pyrazofos. Dithiolanes include isoprothiolane.

[0054] Succinate dehydrogenase inhibitors (SDHI) fungicides (b7) (FRAC code 7) inhibit the respiration of Complex II fungi by inhibiting succinate dehydrogenase, a major enzyme in the Krebs cycle (TCA cycle). When respiration is inhibited, fungi cannot produce ATP, and their growth and reproduction are inhibited. SDHI fungicides include phenylbenzamide, phenyloxoethylthiophenamide, pyridinylethylbenzamide, francarboxamide, and oxathiinecarboxamide. This includes the bactericides thiazole carboxamide, pyrazole-4-carboxamide, N-cyclopropyl-N-benzylpyrazolecarboxamide, N-methoxy-(phenyl-ethyl)-pyrazolecarboxamide, pyridinecarboxamide, and pyrazinecarboxamide. Phenylbenzamide includes benodanil, flutolanil, and mepronil. Phenyloxoethylthiophenamide includes isofetamide. Pyridinylethylbenzamide includes fluopyram. Furancarboxamide includes fenflam. Oxatiincarboxamide includes carboxyne and oxycarboxyne. Thiazolecarboxamide includes tifluzamide. Pyrazole-4-carboxamide includes benzovindiflupir, bixafen, fluveneteram (tentative name, registration number 1676101-39-5), fluindapir, fluxapyroxad, flumetopyr, impilfluxam, isopyrazam, penflufen, penthiopyrad, pyrapropoin (tentative name, registration number 1803108-03-3), sedaxane, and N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methylethyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide. N-cyclopropyl-N-benzylpyrazolecarboxamide includes isoflucipram. N-methoxy-(phenylethyl)-pyrazolecarboxamide includes pidflumetofen. Pyridinecarboxamide includes boscalid. Pyrazinecarboxamide contains pyraziflumid.

[0055] Hydroxy-(2-amino-)pyrimidine fungicides (b8) (FRAC code 8) inhibit nucleic acid synthesis by inhibiting adenosine deaminase. Examples include bupirimate, dimethylmol, and ethylmol.

[0056] Anilinopyrimidine (AP) fungicides (b9) (FRAC code 9) are proposed to inhibit the biosynthesis of the amino acid methionine and the secretion of hydrolytic enzymes that lyse plant cells during infection. Examples include cyprodinil, mepanipyrim, and pyrimethanil.

[0057] N-phenylcarbamate bactericides (b10) (FRAC code 10) inhibit mitosis by binding to β-tubulin and disrupting microtubule association. Inhibition of microtubule association can disrupt cell division, intracellular transport, and cellular structure. An example is diethofencarb.

[0058] "Quinone outside inhibitor (QoI) fungicides (b11)" (FRAC code 11) inhibit complex III of fungal mitochondrial respiration by affecting ubiquinol oxidase. The oxidation of ubiquinol is inhibited at the "quinone outside" (Qo) site of the cytochrome bc1 complex located in the inner mitochondrial membrane of fungi. By inhibiting mitochondrial respiration, they hinder the normal growth and development of fungi. Quinone outside inhibitor fungicides include methoxyacrylate, methoxyacetamide, methoxycarbamate, oxyminoacetate, oxyminoacetamide, and dihydrodioxazine fungicides (collectively known as strobilurin fungicides), as well as oxazolidinedione, imidazolinone, and benzylcarbamate fungicides. Methoxyacrylates include azoxystrobin, chemoxystrobin, enoxastrobin (also known as enestrobrin), fluphenoxystrobin, picoxystrobin, and pyraoxystrobin. Methoxyacetamides include mandestrobin. Methoxycarbamates contain pyraclostrobin, pyramethostropin, and triclopyricarb. Oxyminoacetates contain kresoxime-methyl and trifloxystrobin. Oxyminoacetamides contain dimoxystrobin, phenaminestrobin, metminostrobin, and orysastrobin. Dihydrodioxazines contain fluoxastrobin. Oxazolidinediones contain famoxadone. Imidazolinones contain phenamidone. Benzylcarbamates contain pyribencarb.

[0059] Phenylpyrrole (PP) fungicides (b12) (FRAC code 12) inhibit MAP / histidine kinases, which are involved in osmotic signaling in fungi. Fenpiclonil and fludioxonil are examples of fungicides in this class.

[0060] Azanaphthalene fungicide (b13) (FRAC code 13) is proposed to inhibit signal transduction through an unknown mechanism. It has been confirmed that it inhibits the germination and / or appressorium formation of fungi that cause diseases. Azanafthene fungicides contain aryloxyquinoline and quinazolinone. Aryloxyquinoline contains quinoxyfen. Quinazolinone contains proquinazide.

[0061] "Cellular peroxidation inhibitor bactericides (b14)" (FRAC code 14) are proposed to suppress lipid peroxidation that affects membrane synthesis in fungi. Components of this class, such as etridiazoles, may also affect other biological processes such as respiration and melanin biosynthesis. Cellular peroxidation bactericides include aromatic hydrocarbons and 1,2,4-thiadiazole bactericides. Aromatic hydrocarbon bactericides include biphenyl, chloreneb, dichlorane, quintozen, technazen, and tolclophos-methyl. 1,2,4-thiadiazoles include etridiazoles.

[0062] "Melanin biosynthesis inhibitor-reductase (MBI-R) fungicides (b15)" (FRAC code 16.1) inhibit the naphthal reduction step in melanin biosynthesis. Melanin is necessary for infection of host plants by several fungi. Melanin biosynthesis inhibitor-reductase fungicides include isobenzofuranone, pyrroloquinolinone, and triazolobenzothiazole fungicides. Isobenzofuranone contains phthalides. Pyrroloquinolinone contains pyroquilon. Triazolobenzothiazole contains tricyclazole.

[0063] "Melanin biosynthesis inhibitor-dehydratase (MBI-D) fungicide (b16a)" (FRAC code 16.2) inhibits citalone dehydratase in melanin biosynthesis. Melanin is necessary for infection of host plants by several fungi. Melanin biosynthesis inhibitor-dehydratase fungicides include cyclopropanecarboxamide, carboxamide, and propionamide fungicides. Cyclopropanecarboxamide includes carpropamide. Carboxamide includes diclocimet. Propionamide includes phenoxanil.

[0064] "Melanin biosynthesis inhibitors - polyketide synthase (MBI-P) fungicides (b16b)" (FRAC code 16.3) inhibit polyketide synthase in melanin biosynthesis. Melanin is necessary for infection of host plants by several fungi. Melanin biosynthesis inhibitors - polyketide synthase fungicides include trifluoroethylcarbamate fungicides. Trifluoroethylcarbamate fungicides include tolprocarb.

[0065] "Ketreductase inhibitor (KRI) fungicides (b17)" (FRAC code 17) inhibit 3-keteductase during C4-demethylation in sterol production. Keteductase inhibitor fungicides (also known as sterol biosynthesis inhibitors (SBI): Class III) include hydroxyanilide and aminopyrazolinone. Hydroxyanilide includes fenhexamide. Aminopyrazolinone includes fenpyrazamine. Quinofumelin (tentative name, registration number 861647-84-9) and Ipuflufenokine (tentative name, registration number 1314008-27-9) are also considered to be keteductase inhibitory fungicides.

[0066] "Squalene epoxidase inhibitor bactericide (b18)" (FRAC code 18) (SBI: class IV) inhibits squalene epoxidase in the sterol biosynthesis pathway. Sterols, such as ergosterol, are necessary for membrane structure and function, and are therefore essential for the development of functional cell walls. Consequently, exposure to these fungicides leads to abnormal growth and ultimately death of susceptible fungi. Squalene epoxidase inhibitor fungicides include thiocarbamate fungicides and allylamine fungicides. Thiocarbamates include pyributicarb. Allylamines include naphthifine and terbinafine.

[0067] "Polyoxin disinfectants (b19)" (FRAC code 19) inhibit chitin synthase. Examples include polyoxins.

[0068] Phenylurea fungicides (b20) (FRAC code 20) are proposed to affect cell division. An example is pencyclon.

[0069] "Quinone inside inhibitor (QiI) fungicides (b21)" (FRAC code 21) inhibit complex III of fungal mitochondrial respiration by affecting ubiquinone reductase. The reduction of ubiquinone is inhibited at the "quinone inside" (Qi) site of the cytochrome bc1 complex located in the inner mitochondrial membrane of fungi. By inhibiting mitochondrial respiration, the normal growth and development of fungi are hindered. Quinone inside inhibitor fungicides include cyanoimidazole, sulfamoyltriazole, and picolineamide fungicides. Cyanoimidazole includes cyazofamide. Sulfamoyltriazole includes amisulfrom. Picolinamide includes fenpicoxamide (registration number 517875-34-2).

[0070] "Benzamide and thiazole carboxamide fungicides (b22)" (FRAC code 22) inhibit mitosis by binding to β-tubulin and disrupting microtubule association. Inhibition of microtubule association can disrupt cell division, intracellular transport, and cellular structure. Benzamides include toluamides such as zoxamide. Thiazole carboxamides include ethylaminothiazole carboxamides such as etaboxam.

[0071] Enopyranuronic acid antibiotic fungicides (b23) (FRAC code 23) inhibit fungal growth by affecting protein biosynthesis. An example is blastocydin-S.

[0072] Hexopyranosyl antibiotic fungicides (b24) (FRAC code 24) inhibit fungal growth by affecting phospholipid biosynthesis. An example is kasugamycin.

[0073] "Glucopyranosyl antibiotics: protein synthesis fungicides (b25)" (FRAC code 25) inhibit fungal growth by affecting protein biosynthesis. Examples include streptomycin.

[0074] "Glucopyranosyl antibiotic bactericides (b26)" (FRAC code U18, formerly FRAC code 26 but reclassified as U18) are proposed to inhibit the biosynthesis of trehalase and inositol. Examples include validamycin.

[0075] "Cyanoacetamidooxime fungicide (b27)" (FRAC code 27) contains cymoxanil.

[0076] Carbamate fungicides (b28) (FRAC code 28) are thought to be multi-site inhibitors of fungal growth. These interfere with the synthesis of fatty acids in the cell membrane, and subsequently the cell These are proposed to disrupt membrane permeability. Iodocarb, propamacarb, and prothiocarb are examples of fungicides in this class.

[0077] Oxidative phosphorylation uncoupling fungicides (b29) (FRAC code 29) inhibit fungal respiration by blocking oxidative phosphorylation. By inhibiting respiration, they prevent the normal growth and development of fungi. This class includes dinitrophenyl crotonates such as binapacril, meptyldinocap and dinocap, and 2,6-dinitroanilines such as fluazinam.

[0078] "Organotin fungicides (b30)" (FRAC code 30) inhibit adenosine triphosphate (ATP) synthesis in the oxidative phosphorylation pathway. Examples include fentin acetate, fentin chloride, and fentin hydroxide.

[0079] "Carboxylic acid fungicides (b31)" (FRAC code 31) inhibit fungal growth by acting on deoxyribonucleic acid (DNA) topoisomerase type II (gyrase). An example is oxolinic acid.

[0080] "Heterocyclic aromatic compound fungicides (b32)" (FRAC code 32) are proposed to affect DNA / ribonucleic acid (RNA) synthesis. Heterocyclic aromatic compound fungicides include isoxazoles and isothiazolones. Isoxazoles include himexazoles, and isothiazolones include octylinones.

[0081] "Phosphosphite fungicides (b33)" (FRAC code P07, formerly FRAC code 33 but reclassified as P07) contain phosphite and its various salts (including fosetylaluminum).

[0082] "Phthalamitic acid fungicide (b34)" (FRAC code 34) contains tecrophthalam.

[0083] "Benzotriazine fungicide (b35)" (FRAC code 35) contains triazoxide.

[0084] "Benzene sulfonamide fungicide (b36)" (FRAC code 36) contains fursulfamide.

[0085] "Pyridazinone fungicide (b37)" (FRAC code 37) contains diclomezin.

[0086] Thiophene-carboxamide fungicides (b38) (FRAC code 38) are proposed to affect ATP production. Examples include silthiofames.

[0087] "Complex I NADH oxidoreductase inhibitor bactericide (b39)" (FRAC code 39) inhibits electron transport in mitochondria and includes pyrimidineamines such as diflumetrim, pyrazole-5-carboxamides such as tolfenpyrad, and quinazolines such as phenazaquin.

[0088] Carboxylic acid amide (CAA) fungicides (b40) (FRAC code 40) inhibit cellulose synthetase, preventing the growth of target fungi and causing their death. Carboxylic acid amide fungicides include cinnamic acid amide, carbamate valinamide, and mandelic acid amide fungicides. Cinnamic acid amide includes dimethomorph, flumorph, and pyrimorph. Carbamate valinamide includes benthiavalicarb, benthiavalicarb-isopropyl, iprovalicarb, and It contains luprocarb and valifenarate (also known as valifenaal). Mandelic acid amides include mandipropamide, N-[2-[4-[[3-(4-chlorophenyl)-2-propyne-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulfonyl)amino]butanamide and N-[2-[4-[[3-(4-chlorophenyl)-2-propyne-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(ethylsulfonyl)amino]butanamide.

[0089] Tetracycline antibiotic fungicides (b41) (FRAC code 41) inhibit fungal growth by affecting protein synthesis. Examples include oxytetracycline.

[0090] "Thioccarbamate fungicides (b42)" (FRAC code M12, formerly FRAC code 42 but reclassified as M12) contain metasulfocarb.

[0091] "Benzamide fungicides (b43)" (FRAC code 43) inhibit fungal growth by delocalizing spectrin-like proteins. Examples include pyridinylmethylbenzamides such as fluopicolide and fluopimomid.

[0092] "Microbial fungicides (b44)" (FRAC code BM02, formerly FRAC code 44 but reclassified as BM02) are those that disrupt the cell membranes of fungal pathogens. Microbial fungicides include Bacillus species, such as Bacillus amyloliquefaciens strains AP-136, AP-188, AP-218, AP-219, AP-295, QST713, FZB24, F727, MB1600, D747, TJ100 (also known as strain 1 BE; known from European Patent No. 2962568) and the fungicidal lipopeptides they produce.

[0093] "Quinone outside inhibitors, stigmatine-binding (QoSI) fungicides (b45)" (FRAC code 45) inhibit the mitochondrial respiration of fungal complex III by affecting ubiquinone reductase at the "quinone outside" (Qo) site and stigmatine-binding subsite of the cytochrome bc1 complex. By inhibiting mitochondrial respiration, they disrupt the normal growth and development of fungi. QoSI fungicides include triazolopyrimidylamines such as ametocrazine.

[0094] "Plant extract fungicide (b46)" (FRAC code 46) causes cell membrane disruption. Plant extract fungicides include terpene hydrocarbons, terpene alcohols and terpene phenols, such as extracts from Melaleuca alternifolia (tea tree), and vegetable oils (mixtures), such as eugenol, geraniol, and thymol.

[0095] "Cyanoacrylate fungicides (b47)" (FRAC code 47) bind to the myosin motor domain and affect motor activity and actin association. Cyanoacrylates include fungicides such as phenamacryl.

[0096] Polyene fungicides (b48) (FRAC code 48) bind to ergosterol, the major sterol of the membrane, causing disruption of fungal cell membranes. An example is natamycin (pimaricin).

[0097] "Oxysterol-binding protein inhibitor (OSBPI) bactericide (b49)" (FRAC code 49) binds to the oxysterol-binding protein of oomycetes, and promotes the release of zoospores. These agents inhibit zoospore movement and sporangia germination. Oxysterol-binding fungicides include piperidinyl thiazole isoxazolines such as oxathiapiproline and fluoxapiproline.

[0098] Arylphenyl ketone fungicides (b50) (FRAC code 50, formerly FRAC code U8 but reclassified as 50) inhibit the growth of fungal hyphae. Arylphenyl ketone fungicides include benzophenones such as metraphenone and benzoylpyridines such as pyriophenone.

[0099] "Host plant defense-inducing fungicides (b51)" induce the defense mechanisms of host plants. Host plant defense-inducing fungicides include benzothiadiazole (FRAC code P01), benzoisothiazol (FRAC code P02), thiadiazole carboxamide (FRAC code P03), polysaccharides (FRAC code P04), plant extracts (FRAC code P05), microorganisms (FRAC code P06), and phosphonate fungicides (FRAC code P07, see (b33) above). Benzoisothiazol contains acibenzolar-S-methyl. Benzisothiazol contains probenazole. Thiadiazole carboxamide contains thiadinyl and isothianil. Polysaccharides contain laminarin. Plant extracts include extracts from Reynoutria sachalinensis (giant knotweed). The microorganisms include the cell walls of Bacillus mycoides isolate J and Saccharomyces cerevisiae strain LAS117.

[0100] "Multi-site active fungicides (b52)" are fungicides that inhibit bacterial growth through multiple sites of action and possess contact / preventive activity. Multi-site active fungicides include copper fungicides (FRAC code M01), sulfur fungicides (FRAC code M02), dithiocarbamate fungicides (FRAC code M03), phthalimide fungicides (FRAC code M04), chloronitrile fungicides (FRAC code M05), sulfamide fungicides (FRAC code M06), multi-site contact guanidine fungicides (FRAC code M07), triazine fungicides (FRAC code M08), quinone fungicides (FRAC code M09), quinoxaline fungicides (FRAC code M10), maleimide fungicides (FRAC code M11), and thiocarbamate fungicides (FRAC code M12, see (b42) above). Copper fungicides are typically inorganic compounds containing copper in the copper(II) oxidized state, examples including copper oxychloride, copper sulfate, and copper hydroxide (including compositions such as Bordeaux mixture (tribasic copper sulfate)). Sulfur fungicides are inorganic chemicals containing a ring or chain of sulfur atoms, examples including element sulfur. Dithiocarbamate fungicides are fungicides containing a dithiocarbamate molecular part, examples including felbam, mancozeb, maneb, methylam, propineb, thyram, zinc thiazole, zineb, and ziram. Phthalimide fungicides contain a phthalimide molecular part, examples including holpet, captan, and captahole. Chloronitrile fungicides contain aromatic rings substituted with chloro and cyano, examples including chlorothalonil. Sulfamide fungicides include diclofluanide and trifluanide. Multisite contact guanidine fungicides include guazatine, iminooctadine albesylate, and iminooctadine triacetate. Triazine fungicides contain anilazine. Quinone fungicides contain dithianone. Quinoxaline fungicides contain quinomethionate (also known as thinomethionate). Maleimide fungicides contain fluoroimide.

[0101] "Biological preparations with multiple mechanisms of action (b53)" include drugs of biological origin that exhibit multiple mechanisms of action for which there is no evidence of a dominant mechanism. This class of fungicides includes polypeptides (lectins), phenols, sesquiterpenes, tritepenoids, and coumarin fungicides (FRAC code BM01), such as extracts from the cotyledons of the lupine plant. This class also includes Momilon fungicide (FRAC code BM02, see (b44) above).

[0102] "Bactericides other than those of component (a) and components (b1) to (b53); (b54)" include certain bactericides whose mechanism of action may be unknown. These include (b54.1) "phenylacetamide bactericide" (FRAC code U06), (b54.2) "guanidine bactericide" (FRAC code U12), (b54.3) "thiazolidinedione bactericide" (FRAC code U13), (b54.4) "pyrimidinone-hydrazone bactericide" (FRAC code U14), (b54.5) "4-quinolyl acetate bactericide" (FRAC code U16), (54.6) "tetrazolyloxime bactericide" (FRAC code U17), and "glucopyranosyl antibiotic bactericide" (FRAC code U18, see (b26) above). Phenylacetamide includes cyflufenamide. Guanidine includes dozin. Thiazolidinediones include fluthianil. Pyrimidinone hydrazones include ferimzon. 4-Quinolyl acetate is tebufloquine. Tetrazolyl oxime is picarbutrazox.

[0103] The (b54) class includes bethoxazine, diclobentiazox (tentative name, registration number 957144-77-3), dipimethitrone (tentative name, registration number 16114-35-5), flomethquin, neoasodine (ferric methanearsone), pyrrolnitrin, torniphanide (registration number 304911-98-6), N'-[4-[4-chloro-3-(trifluoromethyl)phenoxy]-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide, 5-fluoro-2-[(4-fluorophenyl)methoxy]-4-pyrimidineamine, and 4-fluorophenyl N-[1-[[[1-(4-cyanophenyl)ethyl]sulfonyl]methyl]propyl]carbamate.

[0104] Additional "bactericides other than those of class (1) to (54)" whose mechanism of action may be unknown or which still cannot be classified include bactericidal compounds selected from components (b54.7) to (b54.12) described below.

[0105] The component (54.7) is (1S)-2,2-bis(4-fluorophenyl)-1-methylethyl N-[[3-(acetyloxy)-4-methoxy-2-pyridinyl]carbonyl]-L-alaninate (tentative name floryl picoxamide, registration number 1961312-55-9), which is thought to be a quinone inside inhibitor (QiI) fungicide (FRAC code 21) that inhibits complex III mitochondrial respiration in fungi.

[0106] The component (54.8) is thought to be a quinone outside inhibitor (QoI) fungicide (FRAC code 45) that inhibits complex III mitochondrial respiration in fungi, and is effective against QoI-resistant strains. This concerns 1-[2-[[[1-(4-chlorophenyl)-1H-pyrazole-3-yl]oxy]methyl]-3-methylphenyl]-1,4-dihydro-4-methyl-5H-tetrasol-5-one (tentative name methyltetraprole, registration number 1472649-01-6).

[0107] Component (54.9) is 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine (tentative name pyridaclomethyl, registration number 1358061-55-8), which is thought to be a tuberine polymerization accelerator and exerts antifungal activity against fungal species belonging to the Ascomycota and Basidiomycota phyla.

[0108] Component (54.10) is thought to inhibit the GWT-1 protein in the glycosylphosphatidylinositol-anchor biosynthesis of Neurospora crassa. (4-phenoxyphenyl)methyl 2-amino-6-methylpyridinyl This concerns n-3-carboxylate (tentative name aminopyriphen, registration number 1531626-08-0).

[0109] The component (b54.11) is given by formula b54.11 [ka] (In the formula, R b1 and R b3 Each is independently a halogen, and R b2 (These are H, halogen, C1-C3 alkyl, C1-C3 haloalkyl, or C3-C6 cycloalkyl.) Regarding the compounds.

[0110] Examples of compounds of formula b54.11 include (b54.11a) methyl N-[[5-[1-(2,6-difluoro-4-formylphenyl)-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, (b54.11b) methyl N-[[5-[1-(4-cyclopropyl-2,6-dichlorophenyl)-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, (b54.11c) methyl N-[[5-[1-(4-chloro-2,6-difluorophenyl)-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, (b Examples include (b54.11d) methyl N-[[5-[1-(4-cyclopropyl-2,6-difluorophenyl)-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, (b54.11e) methyl N-[[5-[1-[2,6-difluoro-4-(1-methylethyl)phenyl]-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, and (b54.11f) methyl N-[[5-[1-[2,6-difluoro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate. The compound of formula b54.11, its use as a bactericide, and its preparation methods are generally known; see, for example, the PCT patent publications, International Publications O2008 / 124092, 2014 / 066120, and 2020 / 097012.

[0111] Methyl The component (b54.12) is given by formula b54.12 [ka] (In the formula, R b4 teeth, [ka] And, R b6 These are C2-C4 alkoxycarbonyl or C2-C4 haloalkylaminocarbonyl. L is CH2 or CH2O, where the atom on the right is bonded to the phenyl ring in formula b54.12. R b5 teeth, [ka] And, R b7 (These are C1-C3 alkyl groups, where the wavy bond indicates that the adjacent double bond is in a (Z)- or (E)- configuration, or a mixture thereof.) Regarding the compounds.

[0112] Examples of compounds of formula b54.12 are (b54.12a)N-(2,2,2-trifluoroethyl)-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-4-oxazolecarboxamide, (b54.12b)ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenoxy]methyl]-1H-pyrazole-4-carboxamide This includes ruboxylate, (b54.12c)ethyl 1-[[4-[[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate, and (b54.12d)ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]-1H-pyrazole-4-carboxylate. The compounds of formula b54.12, their use as bactericides, and methods of preparation are generally known; see, for example, PCT Patent Publication International Publication No. 2008 / 187553 and International Publication International Publication No. 2020 / 056090.

[0113] The embodiments of the present invention described in the summary of the invention include those described below. In the following embodiments, Formula 1 includes its stereoisomers, N-oxides, and salts, and the phrase "compound of Formula 1" includes the definition of substituents as defined in the summary of the invention, unless further defined in the embodiments.

[0114] Embodiment 1. In Equation 1, R 1 A composition comprising components (a) and (b) described in the abstract of the invention, wherein is methyl.

[0115] Embodiment 2. In Equation 1, R 1 A composition comprising components (a) and (b) described in the abstract of the invention, wherein is ethyl.

[0116] Embodiment 3.R 2 A composition comprising components (a) and (b) described in the Outline of the Invention (here, in Formula 1) or Embodiment 1 or 2, which are cyano, halogen, or C1-C2 alkyl.

[0117] Embodiment 4.R 2 A composition comprising components (a) and (b) described in the Outline of the Invention (here, in Formula 1) or Embodiment 1 or 2, wherein the component is cyano, Br, Cl, F, C1-C2 alkyl, or C1-C2 haloalkyl.

[0118] Embodiment 5.R 2 The composition according to Embodiment 4, wherein the element is cyano, Br, Cl, F, C1-C2 alkyl, or halomethyl.

[0119] Embodiment 6.R 2 The composition according to Embodiment 5, wherein the element is cyano, Br, Cl, F, C1-C2 alkyl, or CF3.

[0120] Embodiment 7.R 2 The composition according to Embodiment 6, wherein the element is cyano, Br, Cl, F, or C1-C2 alkyl.

[0121] Embodiment 8.R 2 The composition according to Embodiment 7, wherein the compound is cyano or C1-C2 alkyl.

[0122] Embodiment 9.R 2 The composition according to Embodiment 8, wherein the C1-C2 alkyl group is present.

[0123] Embodiment 10.R2 The composition according to Embodiment 8, wherein it is cyano or methyl.

[0124] Embodiment 11.R 2 The composition according to Embodiment 10, wherein it is methyl.

[0125] Embodiment 12.R 2 The composition according to Embodiment 7, wherein it is Br, Cl or methyl.

[0126] Embodiment 13.R 3 The composition comprising components (a) and (b) according to the Summary of the Invention (herein, in Formula 1) or any one of Embodiments 1 to 12, wherein it is halogen or methyl.

[0127] Embodiment 13a.R 3 The composition according to Embodiment 13, wherein it is halogen

[0128] Embodiment 13b.R 3 The composition according to Embodiment 13, wherein it is Br, Cl, F or methyl.

[0129] Embodiment 14.R 3 The composition according to Embodiment 13, wherein it is Br, Cl or F. [[ID=3​​​​​​​​​​​​​​​​​​​​​​​​​​​3 The composition according to Embodiment 18, wherein the methyl

[0135] Embodiment 20.R 3 The composition according to Embodiment 19, wherein the methyl

[0136] Embodiment 21. Each R 4 A composition comprising, independently, a halogen, cyano, C1-C2 alkyl, C1-C2 alkoxy, C1-C2 haloalkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C2-C4 cyanoalkoxy, C2-C4 alkoxyalkyl, or C2-C4 alkoxyalkoxy, as described in the Outline of the Invention (in Formula 1) or any one of Embodiments 1 to 20.

[0137] Embodiment 22. Each R 4 The composition according to Embodiment 21, wherein the elements are independently halogen, cyano, methyl, methoxy, halomethoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C2-C4 cyanoalkoxy, C2-C4 alkoxyalkyl, or C2-C4 alkoxyalkoxy.

[0138] Embodiment 23. Each R 4 The composition according to Embodiment 22, wherein the elements are independently halogen, cyano, methyl, methoxy, halomethoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, or C2-C4 cyanoalkoxy.

[0139] Embodiment 24. Each R 4 The composition according to Embodiment 23, wherein the elements are independently halogen, cyano, methyl, methoxy, halomethoxy, or C2-C4 cyanoalkoxy.

[0140] Embodiment 25. Each R 4 The composition according to Embodiment 24, wherein the element is independently a halogen, cyano, methyl, or methoxy.

[0141] Embodiment 25a. Each R 4The composition according to embodiment 25, wherein each is independently halogen, cyano or methoxy.

[0142] Embodiment 25b. Each R 4 The composition according to embodiment 25, wherein each is independently halogen, cyano or methyl.

[0143] Embodiment 26. Each R 4 The composition according to embodiment 25, wherein each is independently Br, Cl, F, cyano, methyl or methoxy.

[0144] Embodiment 27. Each R 4 The composition according to embodiment 26, wherein each is independently Br, Cl, F, cyano or methoxy.

[0145] Embodiment 28. Each R 4 The composition according to embodiment 27, wherein each is independently Cl, F, cyano or methoxy.

[0146] Embodiment 29. Each R 4 The composition according to embodiment 27, wherein each is independently Br, Cl or F.

[0147] Embodiment 30. Each R 4 The composition according to embodiment 29, wherein each is independently Cl or F.

[0148] Embodiment 31. Each R 4 The composition according to embodiment 30, wherein each is Cl. Embodiment 32. Each R 4 The composition according to embodiment 30, wherein each is F.

[0149] Embodiment 33. Each R 4 The composition comprising components (a) and (b) according to the summary of the invention (herein, in formula 1) or any one of embodiments 1 to 32, wherein each is independently halogen, cyano or C1-Cx alkoxy.

[0150] Embodiment 34. Each R 4The composition according to Embodiment 33, wherein the halogen is independently present.

[0151] Embodiment 35. Each R 4 The composition according to Embodiment 33, wherein independently, the elements are Br, Cl, F, or cyano.

[0152] Embodiment 36. A composition comprising components (a) and (b) described in any one of the Outline of the Invention (here, in Formula 1) or Embodiments 1 to 35, wherein m is 0, 1, or 2.

[0153] Embodiment 37. The composition according to Embodiment 36, wherein m is 1 or 2.

[0154] Embodiment 38. The composition according to Embodiment 37, wherein m is 1.

[0155] Embodiment 39. The composition according to Embodiment 38, wherein m is 2.

[0156] Embodiment 40. Each R 5 A composition comprising, independently, a halogen, a C1-C2 alkyl, a C2-C4 alkoxyalkyl, a C1-C2 alkoxy, a C1-C2 haloalkoxy, a C2-C4 alkenyloxy, a C2-C4 alkynyloxy, a C2-C4 cyanoalkoxy, or a C2-C4 alkoxyalkoxy, as described in the Outline of the Invention (here, in Formula 1) or any one of Embodiments 1 to 39.

[0157] Embodiment 41. Each R 5 The composition according to Embodiment 40, wherein the elements are independently halogen, methyl, methoxy, halomethoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, or C2-C4 cyanoalkoxy.

[0158] Embodiment 42. Each R 5 The composition according to Embodiment 41, wherein the elements are independently halogen, methyl, methoxy, halomethoxy, C2-C4 alkenyloxy, or C2-C4 cyanoalkoxy.

[0159] Embodiment 43. Each R 5 is independently halogen, methyl, methoxy, halomethoxy or C2-C4 cyanoalkoxy, and the composition according to Embodiment 42.

[0160] Embodiment 44. Each R 5 is independently halogen, methyl or methoxy, and the composition according to Embodiment 43.

[0161] Embodiment 45. Each R 5 is independently Br, Cl, F, methyl or methoxy, and the composition according to Embodiment 44.

[0162] Embodiment 46. Each R 5 is independently Br, Cl, F or methoxy, and the composition according to Embodiment 45.

[0163] Embodiment 46a. Each R 5 is independently Br, Cl or F, and the composition according to Embodiment 46.

[0164] Embodiment 47. Each R 5 is independently Cl, F or methoxy, and the composition according to Embodiment 46.

[0165] Embodiment 48. Each R 5 is independently Cl or F, and the composition according to Embodiment 47.

[0166] Embodiment 49. Each R 5 is independently Br, Cl, F or methyl, and the composition according to Embodiment 45.

[0167] Embodiment 50. Each R 5 is independently F or methyl, and the composition according to Embodiment 49.

[0168] Embodiment 51. Each R 5 is F, and the composition according to Embodiment 50.

[0169] The composition according to formula 1 or any one of embodiments 1 to 51, wherein n is 0, 1 or 2.

[0170] The composition according to embodiment 52, wherein n is 1 or 2.

[0171] The composition according to embodiment 53, wherein n is 1.

[0172] The composition according to embodiment 53, wherein n is 2. [[ID=:14]]

[0173] Embodiment 56. R 6 is H; or R 6a is optionally substituted with at most one substituent selected from C1-C3 alkyl or C1-C3 haloalkyl; or amino, C2-C3 alkenyl, C2-C3 alkynyl, cyclopropyl, CH(=O), S(=O)2OM, S(=O) u R 7 , (C=W)R 8 or OR 9 is the composition according to the summary of the invention (herein, in formula 1) or any one of embodiments 1 to 55, comprising components (a) and (b).

[0174] Embodiment 57. R 6 is H; or R 6a is optionally substituted with at most one substituent selected from C1-C3 alkyl or C1-C3 haloalkyl; or cyclopropyl, S(=O)2OM, S(=O) u R 7 , (C=W)R 8 or OR 9 is the composition according to embodiment 56.

[0175] Embodiment 58. R 6 is H; or R 6a is optionally substituted with at most one substituent selected from C1-C2 alkyl or C1-C2 haloalkyl; or S(=O) u R 7 or OR9 The composition according to Embodiment 57.

[0176] Embodiment 59.R 6 However, H; or R 6a The composition according to Embodiment 58, wherein each C1-C2 alkyl or C1-C2 haloalkyl is optionally substituted with up to one substituent selected from the following.

[0177] Embodiment 60.R 6 The composition according to Embodiment 59, wherein the element is H, C1-C2 alkyl, or C1-C2 haloalkyl.

[0178] Embodiment 61.R 6 The composition according to Embodiment 60, wherein H is methyl or halomethyl.

[0179] Embodiment 62.R 6 The composition according to Embodiment 61, wherein the H is methyl or trifluoromethyl.

[0180] Embodiment 63.R 6 The composition according to Embodiment 62, wherein the element is H or methyl.

[0181] Embodiment 64.R 6 The composition according to Embodiment 63, wherein H is present.

[0182] Embodiment 65. Each R 6a The composition according to Formula 1 or any one of Embodiments 1 to 64, wherein the components are independently cyano, C3-C6 cycloalkyl, or C1-C3 alkoxy.

[0183] Embodiment 66. Each R 6a The composition according to Embodiment 65, wherein the active ingredient is independently cyano, cyclopropyl, or methoxy.

[0184] Embodiment 67. Each R 6a The composition according to Embodiment 66, wherein the active ingredient is independently cyano or cyclopropyl.

[0185] A composition comprising components (a) and (b) described in any one of the Outline of the Invention (here, in Formula 1) or Embodiments 1 to 58, wherein Embodiment 68.u is 0.

[0186] Embodiment 69.R 7 A composition comprising components (a) and (b) described in any one of the Outline of the Invention (in Formula 1) or Embodiments 1 to 58, wherein the component is methyl or halomethyl.

[0187] Embodiment 70. A composition comprising components (a) and (b) described in any one of the Outline of the Invention (here, in Formula 1) or Embodiments 1 to 57, wherein W is O.

[0188] Embodiment 71.R 8 A composition comprising components (a) and (b) described in any one of the Outline of the Invention (in Formula 1) or Embodiments 1 to 57, wherein the components are C1-C3 alkyl, C1-C3 alkoxy, or C1-C3 alkylthio.

[0189] Embodiment 72.R 8 The composition according to Embodiment 71, wherein the element is methyl, ethyl, methoxy, ethoxy, methylthio, or ethylthio.

[0190] Embodiment 73.R 8 The composition according to Embodiment 72, wherein the methyl, methoxy, or methylthio is used.

[0191] Embodiment 74.R 9 However, H; or R 9a C1-C3 alkyl or C1-C3 haloalkyl, each optionally substituted with up to one substituent selected from; or CH(=O), cyclopropyl, S(=O)2OM, or (C=W)R 10 A composition comprising components (a) and (b) as described in the Outline of the Invention (here, in Formula 1) or any one of Embodiments 1 to 58.

[0192] Embodiment 75.R 9 However, H; or R9a The composition according to Embodiment 74, wherein each C1-C2 alkyl or C1-C2 haloalkyl is optionally substituted with up to one substituent selected from the following.

[0193] Embodiment 76. Each R 9a A composition comprising, independently, components (a) and (b) described in any one of the Outline of the Invention (in Formula 1) or Embodiments 1 to 75, which are cyano, C3-C6 cycloalkyl, or C1-C3 alkoxy.

[0194] Embodiment 77. Each R 9a The composition according to Embodiment 76, wherein the active ingredient is independently cyano, cyclopropyl, or methoxy.

[0195] Embodiment 78. Each R 9a The composition according to Embodiment 77, wherein the active ingredient is independently cyano or cyclopropyl.

[0196] Embodiment 79.R 10 However, C1-C3 alkyl, C1-C3 alkoxy or C1-C3 A composition comprising alkylthio components (a) and (b) as described in any one of the Outline of the Invention (in Formula 1) or Embodiments 1 to 78.

[0197] Embodiment 80.R 10 The composition according to Embodiment 79, wherein the element is methyl, ethyl, methoxy, ethoxy, methylthio, or ethylthio.

[0198] Embodiment 81.R 10 The composition according to Embodiment 80, wherein the methyl, methoxy, or methylthio is used.

[0199] Embodiment 82.m is 1, and R 4 A composition comprising components (a) and (b) described in any one of the Outline of the Invention (in Formula 1) or Embodiments 1 to 81, wherein the phenyl ring bond to the rest of Formula 1 is at position 4 (or para).

[0200] Embodiment 83.m is 1, and R 4 A composition comprising components (a) and (b) described in any one of the Outline of the Invention (in Formula 1) or Embodiments 1 to 81, wherein the phenyl ring is bonded to the rest of Formula 1 at position 6 (or ortho).

[0201] Embodiment 84.m is 1, and R 4 However, the phenyl ring bond to the rest of formula 1 is at position 4 (or para), or m is 1, and R 4 A composition comprising, but located at position 6 (or ortho), components (a) and (b) described in any one of the Outline of the Invention (here, in Formula 1) or Embodiments 1 to 81.

[0202] Embodiment 85.m is 2 and 1 R 4 A composition comprising components (a) and (b) described in any one of the Outline of the Invention (in Formula 1) or Embodiments 1 to 81, wherein one component is at position 4 (or para) relative to the bond of the phenyl ring to the rest of Formula 1), and the other is at position 6 (or ortho).

[0203] Embodiment 86.m is 1, and R 4 However, the phenyl ring bond to the rest of formula 1 is at position 4 (or para), or m is 1, and R 4 However, either it is in position 6 (or ortho), or m is 2 and one R 4 A composition comprising components (a) and (b) described in any one of the Outline of the Invention (here, in Formula 1) or Embodiments 1 to 81, wherein one component is located at position 4 (or para), and the other is located at position 6 (or ortho).

[0204] Embodiment 86a.m is 1, and R 4 However, the phenyl ring bond to the rest of formula 1 is at position 4 (or para), or m is 2 and one R 4The composition according to Embodiment 86, wherein one atom is located at position 4 (or para), and the other atom is located at position 6 (or ortho).

[0205] Embodiment 87.n is 1, and R 5 A composition comprising components (a) and (b) described in any one of the Outline of the Invention (here, in Formula 1) or Embodiments 1 to 86a, which are located at the 4th position (or para position) relative to the bond of the nitranilino ring to the rest of Formula 1.

[0206] Embodiment 88.n is 1, and R 5 A composition comprising components (a) and (b) described in any one of the Outline of the Invention (here, in Formula 1) or Embodiments 1 to 86a, which are located at the 6th position (or ortho position) relative to the bond of the nitranilino ring to the rest of Formula 1.

[0207] Embodiment 89.n has 2 and 1 R 5 A composition comprising components (a) and (b) described in any one of the Outline of the Invention (in Formula 1) or Embodiments 1 to 86a, wherein one component is at position 4 (or para) relative to the bond of the nitranilino ring to the rest of Formula 1, and the other is at position 6 (or ortho).

[0208] Embodiment 90.n is 1, and R 5 However, the bond of the nitranilino ring to the rest of Equation 1 is at position 4 (or para), or n is 1, and R 5 However, it is in 6th place (or orthoth position), or n is 2, and one R 5 A composition comprising components (a) and (b) described in any one of the Outline of the Invention (in Formula 1) or Embodiments 1 to 86a, wherein one component is located at position 4 (or para), and the other is located at position 6 (or ortho).

[0209] Embodiment 91.m and n are 1, and R 4However, the phenyl and nitranilino rings are bonded to the rest of Equation 1 at position 4 (or para), and R 5 However, either it is in the 6th position (or the ortho position), or m is 1, and R 4 However, it is in the 4th position (or para position), and n is 2, and one R 5 One is in position 4 (or para), and the other is in position 6 (or ortho), or m and n are each 1, and R 4 However, he is in 4th place (or Paralympic rank), and R 5 However, either it is in the 4th position (or para position), or m is 2 and one R 4 One is in the 4th position (or para position), and the other is in the 6th position (or ortho position), and n is 1, and R 5 A composition comprising, but located at position 6 (or ortho), components (a) and (b) described in any one of the Outline of the Invention (here, in Formula 1) or Embodiments 1 to 90.

[0210] Embodiment 92.m and n are 1, and R 4 However, the phenyl and nitranilino rings are bonded to the rest of Equation 1 at position 4 (or para), and R 5 However, either it is in the 6th position (or the ortho position), or m is 1, and R 4 However, it is in the 4th position (or para position), and n is 2, and one R 5 One is in position 4 (or para), and the other is in position 6 (or ortho), m is 2, and one R 4 One is in the 4th position (or para position), and the other is in the 6th position (or ortho position), and n is 1, and R 5 The composition according to Embodiment 91, wherein the compound is located at position 6 (or ortho).

[0211] Embodiment 93.m and n are 1, and R 4 However, the phenyl and nitranilino rings are bonded to the rest of Equation 1 at position 4 (or para), and R 5 However, either it is in the 6th position (or the ortho position), or m is 1, and R 4However, it is in the 4th position (or para position), and n is 2, and one R 5 The composition according to Embodiment 92, wherein one atom is at position 4 (or para), and the other is at position 6 (or ortho).

[0212] Embodiment 94.m and n are 1, and R 4 However, he is in 4th place (or Paralympic rank), and R 5 The composition according to Embodiment 93, wherein the compound is located at position 6 (or ortho).

[0213] Embodiment 95.m is 1, and R 4 However, it is in the 4th position (or para position), and n is 2, and one R 5 The composition according to Embodiment 93, wherein one atom is at position 4 (or para), and the other is at position 6 (or ortho).

[0214] Embodiment 96. A composition comprising components (a) and (b) as described in any one of the Outline of the Invention or Embodiments 1 to 95, wherein component (a) does not contain the N-oxide of the compound of Formula 1.

[0215] Embodiment 97. Component (a) is 4-(2-bromo-4,6-difluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (compound 1), 3-Chloro-4-[5-[(2-chloro-4-fluoro-6-nitrophenyl)amino]-1,3-dimethyl-1H-pyrazole-4-yl]benzonitrile (compound 18), N-(2-chloro-4-fluoro-6-nitrophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (compound 19), 4-(2-chloro-6-fluorophenyl)-N-(2-fluoro-4-methoxy-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (compound 23), 4-(2,4-difluorophenyl)-N-(2-fluoro-4-methoxy-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (compound 57), 4-(2-bromo-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (compound 60), 4-(2-chloro-4,6-difluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (compound 68), 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-3-ethyl-1-methyl-1H-pyrazole-5-amine (compound 72), N-(2-chloro-4-fluoro-6-nitrophenyl)-4-(2-chloro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazole-5-amine (compound 73), 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-4-methyl-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (compound 93), 4-(2-chloro-4-fluorophenyl)-N-(4-fluoro-2-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (compound 111), 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (compound 112), 4-(2,4-difluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (compound 118), N-(4-chloro-2-fluoro-6-nitrophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (compound 121) and 3-Chloro-4-[5-[(2-fluoro-4-methyl-6-nitrophenyl)amino]-1,3-dimethyl-1H-pyrazole-4-yl]benzonitrile (compound 127) A composition comprising components (a) and (b) described in any one of the Outline of the Invention or Embodiments 1 to 95, which includes a compound selected from the group consisting of the above.

[0216] Embodiment 98. The composition according to Embodiment 97, wherein component (a) comprises a compound selected from the group consisting of compounds 1, 19, 57, 60, 68, 72, 93, 112, 121, and 127.

[0217] Embodiment 99. The composition according to Embodiment 98, wherein component (a) comprises a compound selected from the group consisting of compounds 68, 72, and 112.

[0218] Embodiment 100. The composition according to Embodiment 99, wherein component (a) comprises compound 68.

[0219] Embodiment 101. The composition according to Embodiment 99, wherein component (a) comprises compound 72.

[0220] Embodiment 102. The composition according to Embodiment 99, wherein component (a) comprises compound 112.

[0221] Embodiment 103. A composition comprising components (a) and (b) as described in any one of the Outline of the Invention or Embodiments 1 to 99, wherein component (a) is 4-(2-chloro-4,6-difluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine.

[0222] Embodiment 104. A composition comprising components (a) and (b) as described in any one of the Outline of the Invention or Embodiments 1 to 99, wherein component (a) is 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-3-ethyl-1-methyl-1H-pyrazole-5-amine.

[0223] Embodiment 105. A composition comprising components (a) and (b) as described in any one of the Outline of the Invention or Embodiments 1 to 99, wherein component (a) is 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine.

[0224] Embodiment 106. The composition according to Embodiments 1 to 105, wherein component (b) comprises at least two bactericidal compounds, and component (b) consists of a combination of two components of the two bactericidal compounds (where one of the bactericidal compounds is cyproconazole, difenoconazole, epoxyconazole, flutriafole, metconazole, prothioconazole, or tebuconazole), and the other bactericidal compound is not azoxystrobin, benzovindiflupyr, bixafen, boscalid, fluopyram, fluindapyr, fluxapyroxad, isopyrazam, kresoximmethyl, penthiopyrad, picoxystrobin, proquinazide, pyraclostrobin, quinoxyfen, sedaxane, or trifloxystrobin.

[0225] Embodiment 107. The composition of Embodiment 106, wherein component (b) comprises at least two bactericidal compounds, and component (b) consists of a binary combination of the two bactericidal compounds, wherein one of the bactericidal compounds is cyproconazole, diphenconazole, epoxyconazole, flutriafoll, prothioconazole, or tebuconazole, and the other bactericidal compound is not azoxystrobin, benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, isopyrazam, picoxystrobin, pyraclostrobin, or trifloxystrobin.

[0226] The composition of Embodiment 107, wherein Embodiment 108(b) comprises at least two bactericidal compounds, and component (b) consists of a binary combination of the two bactericidal compounds, wherein one of the bactericidal compounds is cyproconazole, diphenconazole, epoxyconazole, flutriafoll, prothioconazole, or tebuconazole, and the other bactericidal compound is not azoxystrobin, benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, picoxystrobin, pyraclostrobin, or trifloxystrobin.

[0227] Embodiments of the present invention, including Embodiments 1 to 108 described above and any other embodiments described herein, can be combined in any way, and the descriptions of variables in the embodiments apply not only to compositions comprising the compound of Formula 1 and at least one other fungicidal compound, but also to compositions comprising the compound of Formula 1 and at least one invertebrate pest control compound or agent, and to the compound of Formula 1 and its compositions, and further to starting compounds and intermediate compounds useful for the preparation of the compound of Formula 1. Furthermore, embodiments of the present invention, including Embodiments 1 to 108 described above and any other embodiments and any combination thereof, relate to the methods of the present invention. Accordingly, it is worth noting as a further embodiment (a) a composition disclosed above comprising the compound of Formula 1, at least one compound selected from its N-oxide and salt, and at least one invertebrate pest control compound or agent.

[0228] Examples of combinations of Embodiments 1 to 108 are given below.

[0229] Embodiment A. A composition comprising components (a) and (b) described in the summary of the invention, wherein component (a) comprises a compound of formula 1 or a salt thereof, in formula 1, R 1 It is methyl, R 2 These are cyano, halogen, or C1-C2 alkyl groups. R 3 It is a halogen, Each R4 These are independently halogen, cyano, methyl, methoxy, halomethoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, or C2-C4 cyanoalkoxy. Each R 5 These are independently halogen, methyl, methoxy, halomethoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, or C2-C4 cyanoalkoxy. R 6 is H; or R 6a C1-C2 alkyl or C1-C2 haloalkyl, each optionally substituted with up to one substituent selected from; or S(=O) u R 7 OR 9 And, R 6a These are cyano, C3-C6 cycloalkyl, or C1-C3 alkoxy compounds. R 7 It is methyl or halomethyl, R 9 is H; or R 9a Each C1-C2 alkyl or C1-C2 haloalkyl is optionally substituted with up to one substituent selected from, and R 9a The composition is cyano, C3-C6 cycloalkyl, or C1-C3 alkoxy.

[0230] Embodiment B. In Formula 1, R 2 However, it is methyl or ethyl, R 3 However, it is Br, Cl, or F. Each R 4 However, independently, they are halogen, cyano, methyl, or methoxy. m is 1, and R 4 However, either it is in 4th place (or para-place), or m is 1, and R 4 However, either it is in position 6 (or ortho), or m is 2 and one R 4 However, one is in 4th place (or para-place), and the other is in 6th place (or ortho-place), Each R5 However, independently, they are halogen, methyl, or methoxy. n is 1, and R 5 However, it is in the 4th position (or para position), or n is 1, and R 5 However, either it is in position 6 (or ortho), or n is 2, and there is one R 5 However, one is in 4th place (or para-place), and the other is in 6th place (or ortho-place), R 6 The composition according to Embodiment B, wherein the element is H or methyl.

[0231] Embodiment C. In Formula 1, R 2 However, it is methyl, Each R 4 However, independently, they are Br, Cl, F, cyano, or methoxy. Each R 5 However, independently, these are Br, Cl, F, methyl, or methoxy. R 6 The composition according to Embodiment B, wherein H is present.

[0232] Embodiment D. In formula 1, Each R 4 However, independently, they are Br, Cl, or F. Each R 5 However, independently, they are Br, Cl, F, or methoxy. m and n are each 1, and R 4 However, he is in 4th place (or Paralympic rank), and R 5 However, either it is in the 6th position (or the ortho position), or m is 1, and R 4 However, it is in the 4th position (or para position), and n is 2, and one R 5 One is in position 4 (or para), and the other is in position 6 (or ortho), or m is 2 and one R 4 One is in the 4th position (or para position), and the other is in the 6th position (or ortho position), and n is 1, and R 5 The composition according to Embodiment C, wherein the position is at the 6th position (or ortho position).

[0233] Embodiment E. In formula 1, R 4 However, it is either Cl or F, Each R 5 However, independently, they are Cl, F, or methoxy. m and n are each 1, and R 4 However, he is in 4th place (or Paralympic rank), and R 5 However, either it is in the 6th position (or the ortho position), or m is 1, and R 4 However, it is in the 4th position (or para position), and n is 2, and one R 5 However, he is in 4th place (or Paralympic rank), and The composition according to Embodiment D, wherein one of the atoms is located at position 6 (or ortho).

[0234] Embodiment F. A composition comprising components (a) and (b) described in the summary of the invention, wherein component (a) comprises a compound of formula 1 or a salt thereof, in formula 1, R 1 These are C1-C2 alkyl groups, R 2 These are cyano, halogen, C1-C2 alkyl, or C1-C2 haloalkyl, R 3 is a halogen or methyl, Each R 4 These are independently halogen, cyano, nitro, C1-C3 alkyl, C1-C3 haloalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C2-C6 cyanoalkoxy, C2-C6 alkoxyalkyl, or C2-C6 alkoxyalkoxy. Each R 5 R is independently a halogen, C1-C3 alkyl, C2-C6 alkoxyalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C2-C6 cyanoalkoxy, or C2-C6 alkoxyalkoxy, provided that at least one R 5 This is conditional on being selected from halogens, m and n are independently 1, 2, or 3. R 6is H; or R 6a C1-C3 alkyl or C1-C3 haloalkyl, each optionally substituted with up to two substituents independently selected from; or amino, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CH(=O), S(=O)2OM, S(=O) u R 7 (C=W)R 8 OR 9 And, Each R 6a These are independently cyano, C3-C6 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, or C1-C3 alkylsulfonyl. M is either K or Na. u is 0, 1, or 2. R 7 These are C1-C3 alkyl or C1-C3 haloalkyl, W is either O or S. R 8 These are C1-C3 alkyl, C2-C4 alkoxyalkyl, C2-C4 alkylaminoalkyl, C3-C6 dialkylaminoalkyl, C1-C3 alkoxy, C1-C3 alkylthio, or C2-C4 alkylthioalkyl. R 9 is H; or R 9a C1-C3 alkyl or C1-C3 haloalkyl groups independently of C1-C3 alkyl groups, each optionally substituted with up to two substituents selected independently of C1-C3; or CH(=O), C3-C6 cycloalkyl, S(=O)2OM, or (C=W)R 10 And, Each R 9a These are independently cyano, C3-C6 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl, and R 10These are C1-C3 alkyl, C2-C4 alkoxyalkyl, C2-C4 alkylaminoalkyl, C3-C6 dialkylaminoalkyl, C1-C3 alkoxy, C1-C3 alkylthio, or C2-C4 alkylthioalkyl. However, the compound in formula 1 is N-(2-bromo-4-fluoro-6-nitrophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, or 3-Chloro-4-(2-chloro-4-fluorophenyl)-N-(2,4-difluoro-6-nitrophenyl)-1-methyl-1H-pyrazole-5-amine A composition that is not subject to the condition that it is not.

[0235] Embodiment G. In Formula 1, R 1 However, it is methyl, R 2 However, it is cyano, halogen, or C1-C2 alkyl, R 3 However, it is a halogen, Each R 4 However, independently, they are halogens, cyanos, methyls, C1-C2 alkoxys, or C1-C2 haloalkoxys. m is 1, and R 4 However, either it is in 4th place (or para-place), or m is 1, and R 4 However, either it is in position 6 (or ortho), or m is 2 and one R 4 However, one is in 4th place (or para-place), and the other is in 6th place (or ortho-place), Each R 5 However, these are independently halogen, methyl, methoxy, halomethyl, C2-C4 alkenyloxy or C2-C4 cyanoalkoxy, n is 1, and R 5 However, it is in the 4th position (or para position), or n is 1, and R 5 However, either it is in position 6 (or ortho), or n is 2, and there is one R 5 However, one is in 4th place (or para-place), and the other is in 6th place (or ortho-place), R 6 The composition according to Embodiment F, wherein the compound is H or methyl.

[0236] Embodiment H. In Formula 1, R 2 However, it is methyl, Each R 4 However, independently, they are Br, Cl, F, cyano, or methoxy. Each R 5 However, independently, these are Br, Cl, F, methyl, or methoxy. R 6 The composition according to Embodiment G, wherein H is present.

[0237] Embodiment I. In Formula 1, R 4 However, it is Br, Cl, or F. Each R 5 However, independently, they are Br, Cl, F, or methoxy. m and n are each 1, and R 4 However, it is in 4th place, and R 5 However, either it is in 6th place, or m is 1, and R 4 However, it is in 4th place, and n is 2, and one R 5 The composition according to Embodiment H, wherein one is in 4th place and the other is in 6th place.

[0238] Implementation JR 4 However, it is either Cl or F, Each R 5 The composition according to Embodiment I, wherein the active component is independently Cl, F, or methoxy.

[0239] Embodiment K. A composition according to any one of Embodiments A to J, wherein component (a) comprises a compound selected from the group consisting of compound 1, compound 18, compound 19, compound 23, compound 57, compound 60, compound 68, compound 72, compound 73, compound 93, compound 111, compound 112, compound 121, and compound 127.

[0240] Embodiment L. The composition according to Embodiment K, wherein component (a) comprises a compound selected from the group consisting of compound 68, compound 72, and compound 112.

[0241] Embodiment M. The composition according to Embodiment L, wherein component (a) comprises compound 112.

[0242] Embodiment B1. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from methylbenzimidazole carbamate fungicides such as benomyl, carbendazim, fuberidazole thiabendazole, thiophanate, and thiophanate methyl (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0243] Embodiment B2. A composition according to the summary of the invention, wherein component (b) comprises at least one compound selected from dicarboximide fungicides such as (b2) clozolinate, dimethacron, iprodione, procymidone, and vinclozoline (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0244] Embodiment B3. Component (b) is (b3) triforine, butthiobate, pyrifenox, pyrisoxazole, phenalimol, nualimol, trialimol, econazole, imazalil, oxpoconazole, pefurazoate, prochloraz, triflumizole, azaconazole, vitertanol, bromconazole, cyproconazole, difenoconazole, diniconazole (including diniconazole-M), epoxyconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafole, hexaconazole, i A composition according to the summary of the invention, comprising at least one compound selected from demethylation inhibitor bactericides such as mibenconazole, ipconazole, mefentrifluconazole, metconazole, mycrobutanil, penconazole, propiconazole, ipfentrifluconazole, quinconazole, simeconazole, tebuconazole, tetraconazole, triadimephone, triadimeol, triticonazole, uniconazole, and uniconazole-P (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0245] Embodiment B4. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from phenylamide fungicides such as metalaxyl, metalaxyl-M, venalaxyl, venalaxyl-M, flaraxyl, obrace, and oxadixyl (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0246] Embodiment B5. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from amine / morpholine bactericides such as algimorph, dodemorph, fenpropimorph, tridemorph, trimorphamide, fenpropidine, piperalin, and spiroxamine (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0247] Embodiment B6. A composition according to the summary of the invention, wherein component (b) comprises at least one compound selected from phospholipid biosynthesis inhibitor bactericides such as edifenphos, ipropenphos, pyrazophos, and isoprothiolane (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0248] Embodiment B7. A composition according to the summary of the invention, wherein component (b) comprises at least one compound selected from succinate dehydrogenase inhibitor bactericides such as (b7) benodanil, flutolanil, mepronil, isofetamide, fluopyram, fenflam, carboxyne, oxycarboxyne, tifluzamide, benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, flametopyr, impilfluxam, isopyrazam, penflufen, penthiopyrad, pyrapropoin, sedaxane, fluventeram, isoflucipram, pidflumetofen, boscalid, and pyraziflumid (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0249] Embodiment B8. A composition according to the summary of the invention, wherein component (b) comprises at least one compound selected from hydroxy(2-amino-)pyrimidine bactericides such as (b8)bupyrimate, dimethylmol, and etylimole (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0250] Embodiment B9. A composition according to the summary of the invention, wherein component (b) comprises at least one compound selected from anilinopyrimidine fungicides such as cyprodinil, mepanipyrim, and pyrimethanil (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0251] Embodiment B10. Component (b) is an N-phenyl compound such as (b10) diethofencarb. A composition according to the summary of the invention, comprising at least one compound selected from rubamate fungicides (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0252] Embodiment B11. A composition according to the summary of the invention, wherein component (b) comprises at least one compound selected from quinone outside inhibitor bactericides such as (b11) azoxystrobin, chemoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyraoxystrobin, mandestrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, kresoxime-methyl, trifloxystrobin, dimoxystrobin, phenaminestrobin, metminostrobin, orysastrobin, fluoxastrobin, famoxadone, phenamidone, and pyribencarb (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0253] Embodiment B12. A composition according to the summary of the invention, wherein component (b) comprises at least one compound selected from phenylpyrrole bactericidal compounds such as (b12) fenpiclonil and fludioxonil (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0254] Embodiment B13. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from azanafthaene fungicides such as (b13) quinoxyfen and proquinazide (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0255] Embodiment B14. A composition according to the summary of the invention, wherein component (b) comprises at least one compound selected from cell peroxidation inhibitor bactericides such as (b14) biphenyl, chloreneb, dichlorane, quintozen, technazen, tolclophos-methyl, and etridiazole (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0256] Embodiment B15. A composition of the outline of the invention, wherein component (b) comprises at least one compound selected from melanin biosynthesis inhibitors-reductase bactericides such as (b15) phthalide, pyroquilon, and tricyclazole (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0257] Embodiment B16a. A composition of the outline of the invention in which component (b) comprises (b16a) at least one compound selected from melanin biosynthesis inhibitors-dehydratase bactericides such as carpropamide, diclocimeth and phenoxanil (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0258] Embodiment B16b. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from melanin biosynthesis inhibitors-polyketide synthase bactericides such as (b16b) tolprocarb (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0259] Embodiment B17. A composition according to the abstract of the invention, wherein component (b) comprises (b17) at least one compound selected from ketoreductase inhibitor bactericides such as fenhexamide, fenpyrazamine, quinofumerine, and ipuflufenoquin (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0260] Embodiment B18. Component (b) is at least one selected from (b18) squalene epoxidase inhibitor bactericides such as pyributicarb, naphthifine and terbinafine. A composition according to the summary of the invention, comprising the compound (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0261] Embodiment B19. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from polyoxin disinfectants such as (b19) polyoxin (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0262] Embodiment B20. A composition according to the summary of the invention, wherein component (b) comprises at least one compound selected from phenylurea fungicides such as (b20) pencyclon (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0263] Embodiment B21. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from quinone inside inhibitor bactericides such as (b21) cyazofamide, amisulbrom, and fenpicoxamide (registration no. 517875-34-2) (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0264] Embodiment B22. A composition according to the summary of the invention, wherein component (b) comprises (b22) at least one compound selected from benzamide and thiazole carboxamide fungicides such as zoxamide and etaboxam (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0265] Embodiment B23. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from enopyranuronic acid antibiotic bactericides such as (b23) blastosidin-S (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0266] Embodiment B24. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from hexopyranosyl antibiotic bactericides such as kasugamycin (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0267] Embodiment B25. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from (b25) glucopyranosyl antibiotics such as streptomycin: protein synthesis bactericides (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0268] Embodiment B26. A composition according to the abstract of the invention, wherein component (b) comprises (b26) a glucopyranosyl antibiotic such as validamycin, at least one compound selected from trehalase and inositol biosynthesis bactericides (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0269] Embodiment B27. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from cyanoacetylamide oxime fungicides such as (b27) cymoxanil (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0270] Embodiment B28. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from carbamate fungicides such as propamacarb, prothiocarb, and iodocarb (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0271] Embodiment B29. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from oxidative phosphorylated uncoupling fungicides such as fluazinam, binapacril, meptyldinocap, and dinocap (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0272] Embodiment B30. A composition according to the summary of the invention, wherein component (b) comprises at least one compound selected from organotin fungicides such as (b30) fentin acetate, fentin chloride, and fentin hydroxide (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0273] Embodiment B31. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from carboxylic acid bactericides such as (b31) oxolinic acid (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0274] Embodiment B32. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from heterocyclic aromatic fungicides such as (b32)himexazole and octylinone (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0275] Embodiment B33. A composition of the outline of the invention in which component (b) comprises at least one compound selected from phosphonate fungicides such as phosphorous acid containing (b33) fosetylaluminum and various salts thereof (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0276] Embodiment B34. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from phthalic acid disinfectants such as (b34) tecrophthalam (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0277] Embodiment B35. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from benzotriazine fungicides such as (b35) triazoxide (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0278] Embodiment B36. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from benzenesulfonamide fungicides such as (b36) fursulfamide (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0279] Embodiment B37. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from pyridazinone fungicides such as (b37) diclomedin (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0280] Embodiment B38. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from thiophenecarboxamide fungicides such as (b38) silthiofame (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0281] Embodiment B39. Component (b) comprises at least one compound selected from complex I NADH oxidoreductase inhibitor bactericides such as (b39) diflumetrim, tolfenpyrad, and phenazaquin (one composition from any of Embodiments 1-108 and A-M). A composition described in the summary of the invention, including but not limited to the following:

[0282] Embodiment B40. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from carboxylic acid amide fungicides such as (b40) dimethomorph, benthiavalicarb, benthiavalicarb-isopropyl, iprovalicarb, valifenarate, mandipropamide, flumorph, dimethomorph, flumorph, pyrimorph, benthiavalicarb, benthiavalicarb-isopropyl, iprovalicarb, tolprocarb, valifenarate, and mandipropamide (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0283] Embodiment B41. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from tetracycline antibiotic bactericides such as (b41) oxytetracycline (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0284] Embodiment B42. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from thiocarbamate fungicides such as (b42) metasulfocarb (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0285] Embodiment B43. A composition according to the abstract of the invention, wherein component (b) comprises (b43) at least one compound selected from benzamide fungicides such as fluopicolide and fluopimomide (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0286] Embodiment B44. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from (b44) Bacillus amyloliquefaciens strains QST713, FZB24, MB1600, D747, F727, TJ100 (also known as strain 1 BE; known from European Patent No. 2962568) and microbial bactericides such as bactericidal lipopeptides produced therein (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0287] Embodiment B45. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from (b45) a quinone outside inhibitor such as ametocrazine and a stigmatylone-conjugated bactericide (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0288] Embodiment B46. A composition according to the summary of the invention, wherein component (b) comprises at least one compound selected from plant extract fungicides such as Melaleuca alternifoli, eugenol, geraniol, and thymol (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0289] Embodiment B47. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from cyanoacrylate fungicides such as (b47) phenamacryl (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0290] Embodiment B48. A composition of the outline of the invention, wherein component (b) comprises at least one compound selected from polyene fungicides such as (b48) natamycin (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0291] Embodiment B49. A composition according to the summary of the invention, wherein component (b) comprises at least one compound selected from oxysterol-binding protein inhibitor bactericides such as oxathiapiproline and fluoxapiproline (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0292] Embodiment B50. A composition of the outline of the invention, wherein component (b) comprises at least one compound selected from aryl-phenyl-ketone bactericides such as (b50) metraphenone and pyriophenone (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0293] Embodiment B51. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from host plant defense-inducing fungicides such as (b51) acibenzolar-S-methyl, probenazole, thiadinyl, isothianil, laminarin, extracts from Reynoutria sachalinensis and Bacillus mycoides isolate J, and the cell wall of Saccharomyces cerevisiae strain LAS117 (including, but not limited to, any one composition from Embodiments 1 to 108 and A to M).

[0294] Embodiment B52. A composition according to the summary of the invention, wherein component (b) comprises at least one compound selected from multi-site active bactericides such as (b52) copper oxychloride, copper sulfate, copper hydroxide, Bordeaux mixture (tribasic copper sulfate), elemental sulfur, felbam, mancozeb, maneb, methylam, propineb, thyram, zinc thiazole, zineb, ziram, holpet, captan, captahol, chlorothalonil, diclofluanide, trifluanide, guazatin, iminoctadine albesylate, iminoctadine triacetate, anilazine, dithianone, quinomethionate, and fluoroimide (including, but not limited to, any one composition from Embodiments 1 to 108 and A to M).

[0295] Embodiment B53. A composition according to the abstract of the invention, wherein component (b) comprises at least one compound selected from biological fungicides having multiple mechanisms of action, such as (b53) an extract from the cotyledons of a lupine plant (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0296] Embodiment B54. Component (b) is (b54) cyflufenamid, bethoxazine, neoazodine, pyrrolnitrin, tebufloxin, dozin, fluthianil, ferimzon, picarbtrazox, diclobentiazox (registration number 957144-77-3), dipimethitrone (registration number 16114-35-5), flomethquin, torniphanide (registration number 304911-98-6), N'-[4-[4-chloro-3-(trifluoromethyl)phenoxy]-2,5-dimethylphenyl]- A composition according to the summary of the invention, comprising component (a) such as N-ethyl-N-methylmethanimidamide, 5-fluoro-2-[(4-fluorophenyl)methoxy]-4-pyrimidinamine, and 4-fluorophenyl N-[1-[[[1-(4-cyanophenyl)ethyl]sulfonyl]methyl]propyl]carbamate (XR-539), and at least one compound selected from bactericides other than the bactericides of components (b1) to (b53) (including any one composition from Embodiments 1 to 108 and A to M).

[0297] Embodiment B55. A composition according to the summary of the invention, wherein component (b) comprises (1S)-2,2-bis(4-fluorophenyl)-1-methylethyl N-[[3-(acetyloxy)-4-methoxy-2-pyridinyl]carbonyl]-L-alaninate (tentative name floryl picoxamide) (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0298] Embodiment B56. A composition according to the summary of the invention, wherein component (b) comprises 1-[2-[[[1-(4-chlorophenyl)-1H-pyrazole-3-yl]oxy]methyl]-3-methylphenyl]-1,4-dihydro-4-methyl-5H-tetrasol-5-one (tentative name methyltetraprole) (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0299] Embodiment B57. A composition according to the summary of the invention, comprising component (b) 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine (tentative name pyridaclomethyl) (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0300] Embodiment B58. A composition according to the summary of the invention, wherein component (b) comprises (4-phenoxyphenyl)methyl 2-amino-6-methylpyridine-3-carboxylate (tentative name aminopyriphen) (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M).

[0301] Embodiment B59. A composition described in the abstract of the invention (but not limited to, including any one of the compositions from Embodiments 1 to 108 and A to M), wherein component (b) comprises at least one compound selected from (b54.11) (i.e., formula b54.11).

[0302] The component (b54.11) is given by formula b54.11 [ka] (In the formula, R b1 and R b3 Each of them is independently a halogen, R b2 (These are H, halogen, C1-C3 alkyl, C1-C3 haloalkyl, or C3-C6 cycloalkyl.) Regarding the compounds.

[0303] Embodiment B60. Component (b) is methyl N-[[5-[1-(2,6-difluoro-4-formylphenyl)-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, methyl N-[[5-[1-(4-cyclopropyl-2,6-dichlorophenyl)-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, methyl N-[[5-[1-(4-chloro-2,6-difluorophenyl)-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, methyl N-[[5-[ At least one bactericidal agent selected from the group consisting of 1-(4-cyclopropyl-2,6-difluorophenyl)-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, methyl N-[[5-[1-[2,6-difluoro-4-(1-methylethyl)phenyl]-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, and methyl N-[5-[1-[2,6-difluoro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate. A composition according to Embodiment B59, comprising a sex compound.

[0304] Embodiment B60b. The composition according to Embodiment B60, wherein component (b) comprises at least one bactericidal compound selected from the group consisting of methyl N-[[5-[1-(4-cyclopropyl-2,6-dichlorophenyl)-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, methyl N-[[5-[1-(4-chloro-2,6-difluorophenyl)-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, methyl N-[[5-[1-[2,6-difluoro-4-(1-methylethyl)phenyl]-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, and methyl N-[[5-[1-[2,6-difluoro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate.

[0305] Embodiment B61. A composition described in the abstract of the invention (but not limited to, including any one of the compositions of Embodiments 1 to 108 and A to M), wherein component (b) comprises at least one compound selected from (b54.12) (i.e., formula b54.12).

[0306] The component (b54.12) is given by formula b54.12 [ka] (In the formula, R b4 teeth, [ka] And, R b6 These are C2-C4 alkoxycarbonyl or C2-C4 haloalkylaminocarbonyl. L is CH2 or CH2O, where the atom on the right is bonded to the phenyl ring in formula b54.12. R b5 teeth, [ka] And, R b7 (These are C1-C3 alkyl groups, where the wavy bond indicates that the adjacent double bond is in a (Z)- or (E)- configuration, or a mixture thereof.) Regarding the compounds.

[0307] Embodiment B62. The composition according to Embodiment B61, wherein component (b) comprises at least one bactericidal compound selected from the group consisting of N-(2,2,2-trifluoroethyl)-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-4-oxazolecarboxamide, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenoxy]methyl]-1H-pyrazole-4-carboxylate, ethyl 1-[[4-[[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate, and ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]-1H-pyrazole-4-carboxylate.

[0308] Embodiment B62b. The composition according to Embodiment B62, wherein component (b) comprises at least one bactericidal compound selected from the group consisting of N-(2,2,2-trifluoroethyl)-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-4-oxazolecarboxamide and ethyl 1-[[4-[[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate.

[0309] Embodiment B63. Component (b) is azoxystrobin, benzovindiflupyr, boscalid (nicobifen), bixafen, bromconazole, carbendazim, chlorothalonil, copper hydroxide, cyflufenamide, cyproconazole, difenoconazole, dimoxystrobin, epoxyconazole, famoxadone, fenbuconazole, fenpropidine, fenpropimorph, fluindapyr, flusilazole, flutriahol, fluxapyroxad, hexaconazole, ipconazole, kresoximmethyl, manzate, metconazole Zole, metminostrobin, metraphenone, mycrobutanil, penconazole, penthiopyrad, picoxystrobin, prochloraz, propiconazole, proquinazide, prothioconazole, pidflumetofen, pyraclostrobin, pyrametostrobin, pyroxystrobin, pyriophenone, quinoxyfen, tebuconazole, trifloxystrobin, triticonazole, methyl N-[[5-[1-(4-cyclopropyl-2,6-dichlorophenyl)-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carb Mate, Methyl N-[[5-[1-(4-chloro-2,6-difluorophenyl)-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, Methyl N-[[5-[1-[2,6-difluoro-4-(1-methylethyl)phenyl]-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, Methyl N-[[5-[1-[2,6-difluoro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, N-(2,2,2-trifluoro A composition described in the summary of the invention (including, but not limited to, any one of the compositions of Embodiments 1 to 108 and A to M), comprising at least one bactericidal compound (bactericide) selected from the group consisting of ethyl)-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-4-oxazolecarboxamide and ethyl 1-[[4-[[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate.

[0310] Embodiment B64. Component (b) is azoxystrobin, benzovindiflupyr, bixafen, chlorothalonil, copper hydroxide, cyflufenamide, cyproconazole, difenoconazole, dimoxystrobin, epoxyconazole, famoxadone, fenpropidine, fenpropimorph, fluindapyr, flusilazole, flutriafole, flux Sapiroxad, kresoximmethyl, manzate, metconazole, metminostrobin, mettraphenone, mycrobutanil, penthiopyrad, picoxystrobin, propiconazole, proquinazide, prothioconazole, pidflumetofen, pyraclostrobin, pyrametostrobin, pyroxystrobin, pyriophenone, quinoxyfen, tebuconazole, trifloxystrobin, triticonazole, methyl N-[[5-[1-(4-cyclopropyl-2,6-dichlorophenyl)-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, methyl N-[[5-[1-(4-chloro-2,6-difluorophenyl)-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, methyl N-[[5-[1-[2,6-di The composition according to Embodiment B63, comprising at least one compound selected from the group consisting of fluoro-4-(1-methylethyl)phenyl]-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, methyl N-[[5-[1-[2,6-difluoro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, N-(2,2,2-trifluoroethyl)-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-4-oxazolecarboxamide, and ethyl 1-[[4-[[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate.

[0311] Embodiment B65. Component (b) is azoxystrobin, benzovindiflupyr, bixafen, chlorothalonil, copper hydroxide, cyproconazole, difenoconazole, epoxyconazole, fenpropidine, fenpropimorph, fluindapyr, flutriafole, fluxapyroxad, manzate, metminostrobin, picoxystrobin, prothioconazole, pidflumetofen, pyraclostrobin, tebuconazole, trifloxystrobin, methyl N-[[5-[1-(4-cyclopropyl-2,6-dichlorophenyl)-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, methyl N-[[5-[1-(4-chloro-2,6-difluorophenyl)-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, methyl N-[[5 The composition according to Embodiment B64, comprising at least one compound selected from the group consisting of -[1-[2,6-difluoro-4-(1-methylethyl)phenyl]-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, methyl N-[[5-[1-[2,6-difluoro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-yl]-2-methylphenyl]methyl]carbamate, N-(2,2,2-trifluoroethyl)-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-4-oxazolecarboxamide, and ethyl 1-[[4-[[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate.

[0312] Embodiment B66. The composition of Embodiment B65, wherein component (b) comprises at least one compound selected from the group consisting of azoxystrobin, benzovindiflupyr, bixafen, chlorothalonil, copper hydroxide, cyproconazole, epoxyconazole, fenpropidine, fenpropimorph, fluindapyr, flutriafole, fluxapiroxad, manzate, metminostrobin, picoxystrobin, prothioconazole, pidflumetofen, pyraclostrobin, tebuconazole, and trifloxystrobin.

[0313] Of particular note is any one of the embodiments described herein, including Embodiments 1-108, A-M, and B1-B66, in which the reference to Formula 1 includes its salts but does not include its N-oxides, and thus the expression "compound of Formula 1" can be replaced with the expression "compound of Formula 1 or a salt thereof." In the compositions noted herein, component (a) includes a compound of Formula 1 or a salt thereof.

[0314] Furthermore, bactericidal compositions of the present invention, comprising a bactericidal effective amount of the compositions of Embodiments 1 to 108, A to M, and B1 to B66, and at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents, are also noteworthy as embodiments.

[0315] Embodiments of the present invention further include a method for controlling plant diseases caused by fungal plant pathogens, comprising applying a fungicidal effective amount of any one of the compositions of Embodiments 1-108, A-M and B1-B66 (for example, as a composition containing the compounding components described herein) to a plant or a part thereof, or to the seeds or seedlings of a plant. Embodiments of the present invention also include a method for protecting a plant or plant seed from diseases caused by fungal pathogens, comprising applying a fungicidal effective amount of any one of the compositions of Embodiments 1-108, A-M and B1-B66 to a plant or plant seed.

[0316] Some embodiments of the present invention involve controlling or protecting plant diseases that primarily affect plant leaves, and / or applying the compositions of the present invention to plant leaves (i.e., to plants instead of seeds). Preferred uses include the preferred compositions described above, and diseases that are particularly effectively controlled include plant diseases caused by fungal plant pathogens. Combinations of fungicides used according to the present invention can promote disease control and delay the development of resistance.

[0317] Embodiments of the method further include the following:

[0318] Embodiment C1. A method for controlling rust, powdery mildew, and septoria disease, comprising applying a bactericidal effective amount of a composition containing components (a) and (b) described in any one of the Outline of the Invention or Embodiments 1 to 108 to a plant. Methods for protecting plants from diseases selected from a list of diseases.

[0319] Embodiment C2. The method of Embodiment C1, wherein the disease is rust, and component (b) of the composition comprises at least one fungicidal compound selected from (b3) a demethylation inhibitor (DMI) fungicide, (b5) an amine / morpholine fungicide, (b7) a succinate dehydrogenase inhibitor fungicide, (b11) a quinone outside inhibitor (QoI) fungicide, (b13) a methylbenzimidazole carbamate fungicide, and (b52) a multi-site active fungicide.

[0320] Embodiment C3. The method according to Embodiment C2, wherein component (b) of the composition comprises at least one bactericidal compound selected from (b3) a demethylation inhibitor (DMI) bactericidal agent, (b7) a succinate dehydrogenase inhibitor bactericidal agent, and (b11) a quinone outside inhibitor (QoI) bactericidal agent.

[0321] Embodiment C4. The method according to Embodiment C3, wherein component (b) of the composition comprises at least one bactericidal compound selected from (b3) a demethylation inhibitor (DMI) bactericide, (b7) a succinate dehydrogenase inhibitor bactericide, and (b11) a quinone external inhibitor (QoI).

[0322] Embodiment C5. The method according to any one of Embodiments C1 to C4, wherein component (b) of the composition comprises at least one bactericidal compound selected from the group consisting of azoxystrobin, benzovindiflupyr, bixafen, cyproconazole, difenoconazole, epoxyconazole, fenpropimorph, florylpicoxamide, fluindapyr, flutriafole, fluxapyroxad, impilfluxam, isoflucipram, mefentrifluconazole, metminostrobin, picoxystrobin, prothioconazole, pidflumetofen, pyraclostrobin, tebuconazole, and trifloxystrobin.

[0323] Embodiment C6. The method according to Embodiment C5, wherein component (b) of the composition comprises at least one bactericidal compound selected from the group consisting of azoxystrobin, benzovindiflupyr, cyproconazole, epoxyconazole, fluindapyr, fluxapiroxad, metminostrobin, picoxystrobin, prothioconazole, pyraclostrobin, tebuconazole, and trifloxystrobin.

[0324] Embodiment C7. The method according to any one of Embodiments C2 to C6, wherein the disease is Asian soybean rust caused by Phakopsora pachyrhizi.

[0325] Embodiment C8. The method according to any one of Embodiments C2 to C6, wherein the disease is wheat rust caused by Puccinia recondita.

[0326] Embodiment C9. The method according to Embodiment C1, wherein the disease is powdery mildew, and component (b) of the composition comprises at least one fungicidal compound selected from (b3) a demethylation inhibitor (DMI) fungicide, (b11) a quinine external inhibitor (QoI) fungicide, (b13) an azanaphthalene fungicide, and (b52) a multisite active fungicide.

[0327] Embodiment C10. The method according to Embodiment C9, wherein component (b) of the composition comprises at least one bactericidal compound selected from (b3) a demethylation inhibitor (DMI) bactericide, (b11) a quinone external inhibitor (QoI) bactericide, and (b52) a multi-site active bactericide.

[0328] Embodiment C11. The method according to Embodiments C9 and C10, wherein component (b) of the composition comprises at least one bactericidal compound selected from the group consisting of azoxystrobin, chlorothalonil, copper sulfate, cyproconazole, difenoconazole, epoxyconazole, fenpropimorph, florylpicoxamide, flutriafoll, mancozeb, mefentrifluconazole, metminostrobin, picoxystrobin, prothioconazole, pyraclostrobin, tebuconazole, and trifloxystrobin.

[0329] Embodiment C12. The method according to Embodiment C11, wherein component (b) of the composition comprises at least one bactericidal compound selected from the group consisting of cyproconazole, difenoconazole, epoxyconazole, prothioconazole, and tebuconazole.

[0330] Embodiment C13. The method according to Embodiment C10, wherein component (b) of the composition comprises at least one bactericidal compound selected from (b3) DMI bactericides.

[0331] Embodiment C14. The method according to Embodiment C13, wherein component (b) of the composition comprises at least one bactericidal compound selected from the group consisting of cyproconazole, difenoconazole, and prothioconazole.

[0332] Embodiment C15. The method according to Embodiment C10, wherein component (b) of the composition comprises at least one bactericidal compound selected from (b11) QoI bactericidal agents.

[0333] Embodiment C16. The method according to Embodiment C15, wherein component (b) of the composition comprises at least one bactericidal compound selected from the group consisting of azoxystrobin, picoxystrobin, and pyraclostrobin.

[0334] Embodiment C17. Any of Embodiments C9 to C16, wherein the disease is powdery mildew caused by Erysiphe graminis. One method.

[0335] Embodiment C18. The method according to Embodiment C1, wherein the disease is Septoria disease, and component (b) of the composition comprises at least one fungicidal compound selected from (b3) demethylation inhibitor (DMI) fungicides and (b11) quinine external inhibitor (QoI) fungicides.

[0336] Embodiment C19. The method according to Embodiment C18, wherein component (b) of the composition comprises at least one bactericidal compound selected from the group consisting of azoxystrobin, cyproconazole, difenoconazole, epoxyconazole, fenpropimorph, florylpicoxamide, flutriafoll, mefentrifluconazole, metminostrobin, picoxystrobin, prothioconazole, pyraclostrobin, tebuconazole, and trifloxystrobin.

[0337] Embodiment C20. The method according to Embodiment C19, wherein component (b) of the composition comprises at least one bactericidal compound selected from the group consisting of epoxyconazole and fenpropimorph.

[0338] Embodiment C21. The method according to any one of Embodiments C18 to C20, wherein the disease is wheat leaf blight caused by Zymoseptoria tritici.

[0339] Embodiment C22. The method according to Embodiment C1, wherein the disease is Botrytis disease, and component (b) of the composition comprises at least one fungicidal compound selected from (b11) quinone external inhibitor (QoI) fungicides and (b52) multisite active fungicides.

[0340] Embodiment C23. The method according to Embodiment C22, wherein component (b) of the composition comprises at least one bactericidal compound selected from the group consisting of azoxystrobin, chlorothalonil, florylpicoxamide, mancozeb, metminostrobin, picoxystrobin, pyraclostrobin, and trifloxystrobin.

[0341] Embodiment C24. The method according to Embodiment C23, wherein component (b) of the composition comprises at least one bactericidal compound selected from the group consisting of azoxystrobin and chlorothalonil.

[0342] Embodiment C25. The method according to any one of Embodiments C1 to C24, wherein components (a) and (b) are applied in synergistically effective amounts (and in a synergistic ratio to each other).

[0343] Of particular note are embodiments corresponding to Embodiments C1 to C25, relating to a method for controlling plant diseases caused by fungal plant pathogens, which involves applying a bactericidal effective amount of the bactericidal composition of the present invention to a plant or part thereof.

[0344] As noted in the summary of the invention, the present invention also relates to the compound of formula 1 or its N-oxide or salt. It is also noteworthy that embodiments of the present invention, including embodiments 1 to 108, also relate to the compound of formula 1.

[0345] The present invention provides a bactericidal composition comprising the compound of Formula 1 (including all stereoisomers, N-oxides, and salts thereof) and at least one other bactericidal agent. Of notable embodiments of such compositions are compositions comprising compounds corresponding to any of the above embodiments of the compound. It is an object.

[0346] The present invention provides a bactericidal composition comprising (i.e., a bactericidal effective amount) of the compound of Formula 1 (including all stereoisomers, N-oxides, and salts thereof) and at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents. Of particular note as embodiments of such compositions are compositions comprising a compound corresponding to any of the embodiments of the compound described above.

[0347] The present invention provides a method for controlling plant diseases caused by fungal plant pathogens, comprising applying a bactericidal effective amount of a compound of formula 1 (including all stereoisomers, N-oxides, and salts thereof) to a plant or a part thereof or plant seeds. Of particular note as an embodiment of such a method is a method comprising applying a bactericidal effective amount of a compound corresponding to any of the above embodiments of the compound. Of particular note is an embodiment in which the compound is applied as a composition of the present invention.

[0348] Of particular note are the compounds of formula 1A (including all geometric and stereoisomers), their N-oxides, hydrates, and salts, formula 1: [ka] (In the formula, R 2 These are cyano, halogen, or C1-C2 alkyl groups. R 3 It is a halogen, R 4a and R 4b Each of these is independently H or halogen, provided that at least one is halogen. R 5a and R 5b Each of these is independently H, halogen, methyl, or methoxy, provided that at least one is halogen. However, R 3 Cl is and R 4a F is R 4b When H, R 5a(provided that it is H, Br, Cl, I, methyl, or methoxy) The compounds and agricultural compositions containing them, and their use as fungicides.

[0349] Embodiment A1.R 2 However, it is methyl or ethyl, R 3 However, it is Br, Cl, or F. R 4a and R 4b However, each is independently H, Br, Cl, or F. R 5a and R 5b A compound of formula 1A, wherein each of the elements is independently H, Br, Cl, F, or methyl.

[0350] Embodiment B1.R 2 However, it is methyl, R 4a However, it is either Cl or F, R 4b However, it is H, Cl or F, R 5a However, it is H, Cl, F or methyl, R 5b The compound according to Embodiment A1, wherein the compound is H or F.

[0351] Of particular note is a bactericidal composition comprising a bactericidal effective amount of the compound of formula 1A (including all its geometric and stereoisomers, N-oxides, and salts) or one of the counterpart embodiments which are counterparts to embodiments 1 to 107 and embodiments A to M, and at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents. Furthermore, of note is a method for controlling plant diseases caused by fungal plant pathogens, comprising applying a bactericidal effective amount of the compound of formula 1A (including all its geometric and stereoisomers, N-oxides, and salts) or one of the counterpart embodiments to a plant or a part thereof or a plant seed. Of particular note is an embodiment in which the compound of formula 1A is applied as a composition of the present invention.

[0352] The compounds of Formula 1 can be prepared using one or more of the following methods and variations as described in Schemes 1 to 12. R in the compounds of Formulas 1 to 21 below. 1 , R 2 , R 3 , R 4 , R 5 , m, n and R 6 The definition of is as defined above in the summary of the invention unless otherwise specified. Formulas 1a and 1b are subsets of Formula 1. The substituents for the subset formulas are as defined for their parent formulas unless otherwise specified.

[0353] As shown in Scheme 1, the compound of Formula 1 is optionally reacted with the 5-aminopyrazole of Formula 2 and the nitrophenyl compound of Formula 3 (where L) in the presence of a metal catalyst and generally a base, such as potassium tert-butoxide, triethylamine, or potassium carbonate, and a solvent, such as tetrahydrofuran, N,N-dimethylformamide, 1,4-dioxane, toluene, ethanol, methanol, or dimethyl sulfoxide. 1These can be prepared by reaction with a leaving group, such as a halogen (e.g., F, Cl, Br, I) or a sulfonate (e.g., mesylate, triflate, or p-toluenesulfonate). In some cases, the use of a metal catalyst in amounts ranging from catalytic to hyperstoichiometric can accelerate the desired reaction. Typical reaction conditions include, for example, carrying out the reaction with a ligand, such as 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl or 2,2'-bis(diphenylphosphino)1,1'-binaphthalene, in the presence of a metal catalyst, such as a copper salt complex (e.g., CuI with N,N'-dimethylethylenediamine, proline or bipyridyl), a palladium complex (e.g., tris(dibenzylideneacetone)dipalladium(0)), or a palladium salt (e.g., palladium acetate), along with a base, such as potassium carbonate, cesium carbonate, potassium phosphate, sodium phenoxide or sodium tert-butoxide, and optionally an alcohol, such as ethanol, in a solvent, such as N,N-dimethylformamide, 1,2-dimethoxyethane, dimethyl sulfoxide, 1,4-dioxane or toluene. For relevant references, please see PCT Patent Publication International Publication No. 2013 / 126283, Synthesis Example 1, Step C; and International Publication International Publication No. 2010 / 020363, Example 2A. Furthermore, the method of Scheme 1 is illustrated in Example 1, Step C; Example 5, Step C; and Example 3. The compound of Formula 3 is commercially available, or its preparation is known in the art. [ka]

[0354] A general method useful for preparing 5-aminopyrazole of formula 2 is well known in the art; see, for example, Journal fuer Praktische Chemie (Leipzig) 1911, 83, 171 and J.Am.Chem.Soc. 1954, 76, 501. One such method is illustrated in Scheme 2 below, where 5-aminopyrazole of formula 2 is prepared by condensing the compound of formula 4 with hydrazine of formula 5 (e.g., methylhydrazine or ethylhydrazine) in a solvent, e.g., ethanol or methanol, in the optional presence of an acid, e.g., acetic acid, by a general procedure known in the art; see, for example, Synthesis Example 1, Step A; and Synthesis Example 2, Step C in PCT Patent Publication International Publication No. 2012 / 031061. The method of Scheme 2 is also illustrated in Example 1, Step B. [ka]

[0355] Alternatively, as shown in Scheme 3, the 5-aminopyrazole of Formula 2 can also be prepared by reacting the 4-bromo or 4-iodopyrazole of Formula 6 with the boronic acid compound of Formula 7 using well-known transition metal catalyzed cross-coupling reaction conditions. [ka]

[0356] A useful method for preparing the compound of formula 6 is known in the art. Formula 1a (i.e., formula 1, where R 6The compound of formula 8 (where R is H) can be prepared as shown in Scheme 4. In this method, the compound of formula 8 and the hydrazine of formula 5 (e.g., methylhydrazine or ethylhydrazine) are condensed in a solvent, e.g., ethanol or methanol, in the presence of an optionally acid or base catalyst, e.g., acetic acid, piperidine or sodium methoxide, by a general procedure known in the art. For reaction conditions, see PCT Patent Publication International No. 2013 / 116251, Synthesis Example 1, Step C and Example 2, Step B. a The method of Scheme 4, using (where is methyl), is illustrated in Example 2, Step C of the present invention. [ka]

[0357] As shown in Scheme 5, the compounds of Formula 8 can be prepared by reacting the ketene dithioacetal derivative of Formula 9 with the compound of Formula 10 in a solvent, such as toluene, tetrahydrofuran, or dimethoxymethane, at a temperature ranging from about -10°C to the boiling point of the solvent, in the optional presence of a base, such as sodium hydride or ethylmagnesium chloride. For relevant references, see, for example, J. Heterocycl. Chem. 1975, 12(1), 139. Useful methods for preparing the compounds of Formula 9 are known in the art. [ka]

[0358] Furthermore, as shown in Scheme 6, the compound of formula 8 (where R a (These are lower alkyl groups) (e.g., methyl, ethyl, n-propyl) and formula 8a (i.e., R aWhen is H, the tautomer of formula 8 can be prepared via a condensation reaction between the isothiocyanate compound of formula 11 and the carbonyl compound of formula 12 to obtain the intermediate compound of formula 13, which is a salt of the thioamide of formula 8a. The intermediate compound of formula 13 can be used in situ (as illustrated in International Publication No. 2013 / 116251, Synthesis Example 1, step C; and Example 2, step C) or isolated (as illustrated in International Publication No. 2013 / 116251, Example 2, step A). ​​Useful bases for preparing the compounds of formula 13 include sodium or potassium hydrides, alkoxides, hydroxides or carbonates, such as sodium hydride, potassium tert-butoxide, sodium ethoxide, potassium hydroxide, sodium hydroxide or potassium carbonate. Amine bases (e.g., triethylamine or N,N-diisopropylethylamine) can also be used to bring about the condensation of formulas 11 and 12 to the compound of formula 13. Various solvents, such as tetrahydrofuran, diethyl ether, toluene, N,N-dimethylformamide, alcohols (e.g., ethanol), esters (e.g., ethyl acetate or isopropyl acetate), or mixtures thereof, are useful. As those skilled in the art will understand, the solvent is selected for its compatibility with the base. The reaction temperature can range from -78°C to the boiling point of the solvent. One useful mixture of base and solvent combination is potassium tert-butoxide or potassium tert-pentoxide in tetrahydrofuran to which a solution of the isothiocyanate of formula 11 and the carbonyl compound of formula 12 can be added, either combined in one solution or, preferably, separately by adding the carbonyl compound followed by the isothiocyanate. Typically, this reaction is carried out at -70 to 0°C. The salt of formula 13 is acidified to form the ketothioamide compound of formula 8a, or R a X 1 (Formula 14) (where R a is a lower alkyl group (e.g., methyl, ethyl, n-propyl), and X 1It can be alkylated with a nuclear leaving group (i.e., a nucleophilic leaving group, e.g., Br, I, OS(O)2CH3) to form the corresponding compound of formula 8. This general method is known in the chemical literature; see, for example, Zhurnal Organicheskoi Khimii 1982,18(12),2501. From the intermediate compound of formula 13 (not isolated), the compound of formula 8 (where R a The method of Scheme 6 for preparing (where is methyl) is illustrated in Synthesis Example 1, Step C of PCT Patent Publication International Publication No. 2013 / 116251. Furthermore, Example 2, Step C illustrates the preparation of the compound of Formula 8. [ka]

[0359] The ketothioamide of formula 8a can also be prepared by reacting the corresponding ketoamide with a sulfurizing agent, such as Lawson's reagent or P2S5; see, for example, Helv. Chim. Act. 1998, 81(7), 1207.

[0360] As shown in Scheme 7, the compound of formula 1 is preferably mixed with the 1H-pyrazole compound of formula 15 and formula R in the presence of a base, such as 1,8-diazabicyclo[5.4.0]undec-7-ene, potassium carbonate, or potassium hydroxide, and a solvent, such as N,N-dimethylformamide, tetrahydrofuran, toluene, or water. 1 -L 2 Methylating agent (wherein R 1 is methyl or ethyl, L 2These compounds can also be prepared by reacting them with a leaving group, such as a halogen (e.g., Cl, Br, I), a sulfonate (e.g., mesylate, triflate, or p-toluenesulfonate), or a phosphate (e.g., dimethyl phosphate). General procedures for this type of methylation are well known in the art and can be readily adapted to prepare the compounds of the present invention. Particularly useful methylating agents include diazomethane and iodomethane using general procedures known in the art, such as those described in Canada Journal of Chemistry 1986, 64, 2211-2219 and Heterocycles 2000, 53(12), 2775-2780. [ka]

[0361] The compound of formula 15 can be prepared by condensing the compound of formula 8 with hydrazine in a manner similar to the method of scheme 4. This method is described in Chemistry of Heterocyclic Compounds 2005, 41(1), 105-110.

[0362] In an alternative method, as shown in Scheme 8, the compound of Formula 1 can be prepared by the reaction of 4-bromo or 4-iodopyrazole of Formula 16 with an organometallic compound of Formula 17 under transition metal catalyzed cross-coupling conditions in the presence of a suitable palladium, copper, or nickel catalyst. In this method, the compound of Formula 17 is an organoboronic acid (e.g., M 1 (is B(OH)2), organoboronic acid esters (e.g., M 1 is B(-OC(CH2)3O-), an organic trifluoroborate (for example, M 1 (This is BF3K), organotin reagents (e.g., M 1 (These are Sn(n-Bu)3, Sn(Me)3), Grignard reagents (e.g., M 1 (is MgBr or MgCl) or organozinc reagents (e.g., M 1(wherein is ZnBr or ZnCl). Suitable metal catalysts include, but are not limited to, palladium(II) acetate, palladium(II) chloride, tetrakis(triphenylphosphine)palladium(II), bis(triphenylphosphine)palladium(II) dichloride, dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II), bis(triphenylphosphine)dichloronickel(II), and copper(I) salts (e.g., copper(I) iodide, copper(I) bromide, copper(I) chloride, copper(I) cyanide, or copper(I) triflate). The optimal conditions, as those skilled in the art will understand, are the counterions (i.e., M) attached to the catalyst and coupling reagent used. 1 The reaction is determined by the following factors. In some cases, the addition of a ligand, such as a substituted phosphine or substituted bisphosphinoalkane, promotes the reactivity. The presence of a base, such as an alkali carbonate, tertiary amine, or alkali fluoride, may also be necessary for some reactions involving the organoboron reagent of formula 17. For an overview of this type of reaction, see E. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis, John Wiley and Sons, Inc., New York, 2002; N. Miyaura, Cross-Coupling Reactions: A Practical Guide, Springer, New York, 2002; H. Brown et al., Organic Synthesis via Boranes, Vol.3, Aldrich Chemical Co., Milwaukee, WI, 2002; Suzuki et al., Chemical Review See 1995, 95, 2457-2483 and Molander et al., Accounts of Chemical Research 2007, 40, 275-286. Also, the method of Scheme 8 is described in PCT Patent Publication International Publication No. 2010 / 101973 and International Publication International Publication No. 2012 / 031061. This is illustrated by the example. [ka]

[0363] As shown in Scheme 9, the pyrazole intermediate of formula 16 can be readily prepared from the corresponding pyrazole of formula 18 by treatment with a halogenating agent. Suitable halogenating agents for this method include N-bromosuccinimide (NBS), N-iodosuccinimide (NIS), bromine, sodium bromitite, thionyl chloride, oxalyl chloride, phenylphosphonic acid dichloride, or phosgene. Particularly useful are N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS). Suitable solvents for this reaction include, for example, N,N-dimethylformamide, N,N-dimethylacetamide, dichloromethane, chloroform, chlorobutane, benzene, xylene, chlorobenzene, tetrahydrofuran, p-dioxane, and acetonitrile. Optionally, organic bases, such as triethylamine, pyridine, and N,N-dimethylaniline, can be added. The typical reaction temperature is in the range of approximately ambient temperature ~200°C. For typical procedures, please refer to Synthesis 2006, 17, 2855-2864; Journal of Medicinal Chemistry 2005, 48, 6843-6854; Journal of Medicinal Chemistry 2007, 50, 3086-3100 and Journal of Medicinal Chemistry 2005, 48, 4420-4431. [ka]

[0364] As shown in Scheme 10, the compound of Formula 18 can be prepared from the corresponding compound of Formula 19 by a procedure similar to that used for the method of Scheme 1. The compound of Formula 19 is commercially available or can be prepared by methods known in the art. [ka]

[0365] Compounds of Formula 1 and their intermediates described herein can be subjected to various electrophilic, nucleophilic, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents, thereby providing other functionalized compounds of Formula 1. For example, as shown in Scheme 11, Formula 1b (i.e., Formula 1, where (R 5 ) n The compound of formula 20 (where L is CH3) is prepared in the presence of a catalyst, for example, [1,1'-bis(diphenylphosphino)ferrocene]palladium chloride (II) dichloromethane adduct, preferably in the presence of a base, for example, 1,8-diazabicyclo[5.4.0]undeca-7-ene, cesium carbonate, or potassium hydroxide, and a solvent, for example, N,N-dimethylformamide, tetrahydrofuran, 1,4-dioxane, ethanol, toluene, or water, and the compound of formula 20 (where L 3 The reagent can be prepared by the reaction of a leaving group (e.g., halogen (e.g., Br, I) or sulfonate (e.g., mesylate, triflate, p-toluenesulfonate)) with a reagent (e.g., 2,4,6-trimethylboroxine or tetramethylstannane). The method of Scheme 11 is illustrated in Example 4, Step A and Example 4, Step B of PCT Patent Publication International Publication No. 2013 / 192126.

[0366] Compounds of formula 20 can be prepared by the methods described in PCT Patent Publications International Publication No. 2010 / 101973 and International Publication No. 2012 / 031061. Those skilled in the art will recognize that, in some cases, the preparation of the N-protected compound of formula 20 before the interconversion of functional groups facilitates obtaining the desired product. The selection and use of appropriate N-protecting groups will be obvious to those skilled in the art; for representative examples, see TW Greene and PGMWuts, Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991. Step A of this Example 4 illustrates the preparation of the N-Boc protected compound of formula 20. [ka]

[0367] Similar to the method of Scheme 11, the compound of Formula 20 can be treated with potassium (trifluoromethyl)trimethoxyborate to provide the trifluoromethyl analog of Formula 1b.

[0368] In another example, as shown in Scheme 12, the compound of formula 1 (where R 6 (is anything other than H) is R 6 Reaction with an electrophile (i.e., formula 21) yields the corresponding compound of formula 1 (where R 6 It can be prepared from (where is H). Typically, the reaction is carried out in the presence of a base, such as sodium hydride and a polar solvent, such as N,N-dimethylformamide. In this situation, the expression "R 6 "Electrophilic reagents containing" are nucleophiles (i.e., R 6 When is H, R (the nitrogen atom in Equation 1) 6 It refers to a compound that can transfer parts. Often, R 6 Electrophiles containing formula R 6 X 2 It has, in the formula, X 2 R is a nuclear leaving group (i.e., a leaving group in a nucleophilic reaction). Typical nuclear leaving groups include halides (e.g., Br, Cl, I) or sulfonates (e.g., mesylates, triflates, p-toluenesulfonate). However, R 6 Some electrophiles, including R, do not contain nuclear leaving groups; one example is sulfur trioxide (SO3), which is R 6 When is H, the deprotonation of the nitrogen atom in equation 1 (for example, equation M + H - (In the formula, M + It can be bonded to the nitrogen atom as a -SO3M substituent after being bonded to a base (which is a cation). [ka]

[0369] It is recognized that some of the reagents and reaction conditions described above for preparing the compound of Formula 1 may be incompatible with certain functional groups present in the intermediate. In these cases, employing a series of protection / deprotection steps in the synthesis or interconversion of functional groups will help obtain the desired reaction product. The use and selection of protecting groups will be obvious to those skilled in chemical synthesis (e.g. For example, TWGreene and PGMWuts, Protective Groups in Organic Synthesis, 2 nd (See ed.;Wiley: New York, 1991). Those skilled in the art will recognize that in some cases, it may be necessary to perform additional, ordinary synthetic steps not described in detail after introducing the given reagents shown in any of the individual schemes in order to complete the synthesis of the compounds of Formula 1. Furthermore, those skilled in the art will recognize that it may be necessary to combine the steps described in the above schemes in an order different from the specific order presented for preparing the compounds of Formula 1.

[0370] Furthermore, those skilled in the art will recognize that the compounds and intermediates of Formula 1 described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

[0371] Those skilled in the art who use the preceding description will likely be able to utilize the present invention to its fullest extent without any extra effort. Therefore, the following examples are provided merely as illustrations and do not limit the present disclosure in any way. The steps in the following examples illustrate the procedure for each step in the overall synthetic transformation, and the starting materials for each step do not necessarily have to be prepared by a specific preparation operation whose procedure is described in other examples or steps. Percentages are by weight unless otherwise indicated, except in the case of chromatographic solvent mixtures. Parts and percentages in the case of chromatographic solvent mixtures are by volume unless otherwise specified. 1 The 1H NMR spectrum is reported in ppm low field from tetramethylsilane, where 's' means singleline, 'd' means doubleline, 't' means tripleline, 'm' means multiline, 'br s' means broad singleline, and 'dd' means doubleline doubleline. [Examples]

[0372] Example 1 Preparation of 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (compound 112) Step A: Preparation of α-acetyl-2-chloro-4-fluorobenzeneacetonitrile A mixture of sodium methoxide solution (30% in methanol, 85 mL, 0.47 mol) in toluene (400 mL) was heated to 120°C using a Dean-Stark trap to remove methanol azeotrope. After cooling to 90°C, 2-chloro-4-fluorobenzeneacetonitrile (40.0 g, 0.24 mol) in ethyl acetate (200 mL) was added dropwise to the reaction mixture. The reaction mixture was stirred at 90°C for 1 hour, and then hydrochloric acid (1 N, 30 mL) was added. The resulting mixture was extracted with ethyl acetate (3 × 250 mL), and the combined organic extract was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting material was purified by column chromatography on silica gel (eluted with ethyl acetate-petroleum ether in a 3:7 ratio) to obtain the title compound as a white solid (35 g). 1 H NMR(CDCl3): δ7.49(dd,1H),7.24(dd,1H),7.14-7.09(m,1H),5.13(s,1H),2.36(s,3H).

[0373] Step B: Preparation of 4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine To a mixture of α-acetyl-2-chloro-4-fluorobenzeneacetonitrile (i.e., the product of step A) (28 g, 0.13 mol) in ethanol (400 mL), methylhydrazine sulfate (28.6 g, 0.20 mol) and sodium acetate (21.7 g, 0.27 mol) were added. The reaction mixture was heated at 120 °C for 12 hours, then under reduced pressure. The mixture was concentrated below, and the solvent was removed. The resulting mixture was poured into ice water (500 mL), filtered, and a white solid was collected. The solid was rinsed with water and pentane, and then dried to obtain the title compound as an off-white solid (24 g). 1 H NMR(CDCl3): δ 7.45(dd,1H),7.27(t,1H),7.23-7.12(m,1H),4.89(s,2H),3.49(s,3H).

[0374] Step C: Preparation of 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine To a mixture of 4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (i.e., the product of step B) (1.2 g, 5.0 mmol) in tetrahydrofuran (40 mL), potassium tert-butoxide (1 M in THF, 10 mL, 10 mmol) was added gradually at 0°C. The reaction mixture was stirred at 0°C for 1 hour, and then 1,2-difluoro-3-nitrobenzene (0.85 g, 5.3 mmol) was added dropwise. After 30 minutes at 0°C, an aqueous solution of saturated ammonium chloride was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate (100 mL). The aqueous layer was further extracted with ethyl acetate (2 × 40 mL), and the combined organic extracts were washed with saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The material thus obtained was purified by column chromatography on silica gel (elution with 40% ethyl acetate in petroleum ether) to obtain the title compound, which is the compound of the present invention, as a yellow solid (1.1 g). 1 H NMR(CDCl3):δ 8.59(s,1H),7.59(d,1H),7.31(d,1H),7.2(d,1H),7.09(t,1H),7.04-7.01(m,1H),6.82-6.86(m,1H),3.74(s,3H),1.97(s,3H).

[0375] Example 2 Preparation of 3-chloro-4-[5-[(2-fluoro-6-nitrophenyl)amino]-1,3-dimethyl-1H-pyrazole-4-yl]benzonitrile (compound 113) Step A: Preparation of 3-chloro-4-(2-oxopropyl)benzonitrile To a mixture of 4-amino-3-chlorobenzonitrile (50.0 g, 0.33 mol) in diethyl ether (500 mL), boron trifluoride diethyl etherate (61 mL, 0.50 mol) was added at -10°C. The reaction mixture was stirred at -10°C for 10 minutes, and then tert-butylnitride (48 mL, 0.4 mol) was added. After 20 minutes at -10°C, the reaction mixture was warmed to room temperature, stirred for 2 hours, and then filtered to collect a white solid. The white solid was pulverized with diethyl ether and pentane (1:1, 300 mL), filtered, and dried to obtain the intermediate compound 2-chloro-4-cyanobenzenediazonium tetrafluoroborate as an off-white solid (72 g).

[0376] To a mixture of 2-chloro-4-cyanobenzenediazonium tetrafluoroborate (72 g, 0.33 mol) in dimethylformamide (500 mL), isopropenyl acetate (354 mL, 3.2 mol) was added at -10°C. The reaction mixture was stirred at -10°C for 20 minutes, and then 4-aminomorpholine (1.0 mL) in dimethyl sulfoxide (40 mL) was added. After 1 hour, ice-cold water (1000 mL) was added, and the resulting mixture was extracted with ethyl acetate (3 × 250 mL). The combined organic extract was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting material was purified by column chromatography on silica gel (eluted with ethyl acetate-petroleum ether in a 1:4 ratio) to obtain the title compound as a solid (52 g). 1 H NMR(CDCl3): δ 7.69(s,1H),7.53(d,1H),7.32(d,1H),3.93(s,2H),2.28(s,3H).

[0377] Step B: Preparation of 1-fluoro-2-isothiocyanato-3-nitrobenzene To a mixture of 1,2-dichlorobenzene (10 mL) and 2-fluoro-6-nitrobenzeneamine (1.0 g, 6.4 mmol), two drops of dimethylformamide were added at 0°C, followed by thiophosgene (1.46 mL, 19 mmol). The reaction mixture was heated at 160°C for 1 hour, cooled to room temperature, and concentrated under reduced pressure. The resulting material was purified by column chromatography on silica gel (eluted with 1:9 ethyl acetate-petroleum ether) to obtain the title compound as oil (0.91 g). 1 H NMR(CDCl3)δ 7.88(d,1H),7.46(t,1H),7.36(m,1H).

[0378] Step C: Preparation of 3-chloro-4-[5-[(2-fluoro-6-nitrophenyl)amino]-1,3-dimethyl-1H-pyrazole-4-yl]benzonitrile To a mixture of 3-chloro-4-(2-oxopropyl)benzonitrile (i.e., the product of step A) (1.0 g, 5.2 mmol) in tetrahydrofuran (20 mL), potassium tert-butoxide (0.7 g, 6.2 mmol) was added at -10°C. After 30 minutes at -10°C, 1-fluoro-2-isothiocyanato-3-nitrobenzene (i.e., the product of step B) (0.99 g, 5.0 mmol) in tetrahydrofuran (10 mL) was added to the reaction mixture, and stirring was continued for about 15 minutes to obtain a reaction mixture containing the intermediate compound 4-[1-[[(2-chloro-6-nitrophenyl)amino]mercaptomethylene]-2-oxopropyl]-3-chloro-benzonitrile potassium salt, which is the potassium salt of α-acetyl-N-(2-chloro-6-nitrophenyl)-2-chloro-4-cyanobenzeneethanethioamide. Iodomethane (1.2 mL, 19 mmol) was added to the reaction mixture. After 20 minutes at -10°C, the reaction temperature was reduced to 0°C, and acetic acid (5.0 mL) and methylhydrazine (85% of the volume in water, 0.5 g, 10 mmol) were added. The reaction mixture was warmed to room temperature and heated under reflux for 2 hours, then poured into ice-cold water (30 mL) and ethyl acetate (20 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2 × 10 mL). The combined organic extracts were washed with saturated sodium chloride solution (20 mL), dried on sodium sulfate, filtered, and concentrated under reduced pressure. The resulting material was purified by column chromatography on silica gel (eluted with ethyl acetate-petroleum ether in a 2:3 ratio) to obtain the title compound, the compound of the present invention, as a pale yellow solid (0.850 g). 1 H NMR(CDCl3)δ 8.71(d,1H),7.85(d,1H),7.64-7.58(m,2H),7.34-7.25(m,2H),6.87-6.81(m,1H),3.75(s,3H),1.99(s,3H).

[0379] Example 3 Preparation of N-(4-bromo-2-fluoro-6-nitrophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (compound 61) To a mixture of 4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (i.e., the product of Example 1, Step B) (0.5 g, 2.1 mmol) in tetrahydrofuran (30 mL), potassium tert-butoxide (1 M in THF, 4.2 mL, 4.2 mmol) was added gradually at 0°C. The reaction mixture was stirred at 0°C for 1 hour, and then 5-bromo-1,2-difluoro-3-nitrobenzene (0.54 g, 2.3 mmol) was added dropwise. After 30 minutes at 0°C, an aqueous solution of saturated ammonium chloride was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate (100 mL). The aqueous layer was further extracted with ethyl acetate (2 × 40 mL), and the combined organic extracts were washed with saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The material thus obtained was purified by column chromatography on silica gel (elution with 40% ethyl acetate in petroleum ether) to obtain the title compound, which is the compound of the present invention, as a yellow solid (0.45 g). 1 H NMR(CDCl3): δ 8.69(br s,1H),7.77(t,1H),7.66(dd,1H),7.27(dd,2.0Hz,1H),7.09-7.06(m,2H),3.73(s,3H),1.97(s,3H).

[0380] Example 4 Preparation of 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-4-methyl-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (compound 93) Step A: Preparation of 1,1-dimethylethyl N-(4-bromo-2-fluoro-6-nitrophenyl)-N-[4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-yl]carbamate To a mixture of N-(4-bromo-2-fluoro-6-nitrophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (i.e., the product of Example 3) (1 g, 2.2 mmol) and triethylamine (1.24 mL, 8.9 mmol) in dichloromethane (20 mL), di-tert-butyl dicarbonate (1.46 g, 6.7 mmol) was added at 0°C. The reaction mixture was warmed to room temperature, stirred overnight, then diluted with water (20 mL) and extracted with dichloromethane (2 × 20 mL). The combined organic extract was washed with saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting material was purified by column chromatography on silica gel (eluted with 40% ethyl acetate in petroleum ether) to obtain the title compound as a yellow solid (750 mg). 1 H NMR(CDCl3):δ 7.85(s,1H),7.78(s,1H),7.52-7.47(m,1H),7.17-7.19(m,1H),6.97-6.88(m,1H),3.8(s,3H),1.96(s,3H),1.49(s,9H).

[0381] Step B: Preparation of 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-4-methyl-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine A mixture of 1,1-dimethylethyl N-(4-bromo-2-fluoro-6-nitrophenyl)-N-[4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-yl]carbamate (i.e., the product of step A) (600 mg, 1.07 mmol), potassium carbonate (372 mg, 2.7 mmol), dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane complex (1:1) (40 mg, 0.05 mmol), and trimethylboroxine (0.54 mL, 3.9 mmol) in 1,4-dioxane (20 mL) was heated under reflux for 3 hours. The reaction mixture was diluted with water (15 mL) and extracted with ethyl acetate (2 × 10 mL). The combined organic extracts were washed with saturated sodium chloride aqueous solution (3 × 5 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The material thus obtained was dissolved in dichloromethane and trifluoroacetic acid (3:1; 4 mL) and stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the resulting material was dissolved in dichloromethane (5 mL) and washed with saturated sodium bicarbonate aqueous solution (2 mL). The aqueous layer was further extracted with dichloromethane (3 × 10 mL). The combined organic extract was washed with saturated sodium chloride solution, dried on sodium sulfate, filtered, and concentrated under reduced pressure. The resulting material was purified by column chromatography on silica gel (eluted with 40% ethyl acetate in petroleum ether) to obtain the title compound, which is the compound of the present invention, as a yellow solid (210 mg). 1 H NMR(CDCl3)δ 8.41(s,1H),7.45(s,1H),7.24-7.15(m,2H),7.1-7.01(m,2H),3.72(s,3H),2.15(s,3H),1.95(s,3H).

[0382] Example 5 3-Chloro-4-[5-[(2-fluoro-6-nitrophenyl)amino]-1,3-di Preparation of alternatives to methyl-1H-pyrazole-4-yl]benzonitrile (compound 113) Step A: Preparation of 1-methylhydrazine carbonitride A solution of cyanogen bromide (13.5 g, 127.5 mmol) and dichloromethane (250 mL) was cooled to 0°C, and then a mixture of methylhydrazine (85% aqueous solution, 6.0 g, 127.5 mmol), sodium carbonate (7.5 g, 63.9 mmol), and water (60 mL) was added dropwise with vigorous stirring. After the visible signs of gas generation ceased, the aqueous layer was separated and extracted with dichloromethane (3×). The combined organic layers were dried on magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain the title compound as oil (6.0 g).

[0383] Step B: Preparation of 4-(5-amino-1,3-dimethyl-1H-pyrazole-4-yl)-3-chlorobenzonitrile A mixture of 3-chloro-4-(2-oxopropyl)benzonitrile (13.7 g, 71.4 mmol) and 1-methylhydrazinecarbonitride (i.e., the product of step A) (6.0 g, 86 mmol) was heated at 60°C with stirring. After 48 hours, the reaction mixture was dissolved in dichloromethane (100 mL) and water (100 mL), the layers were separated, and the aqueous layer was extracted with dichloromethane (3 ×). The combined organic layers were dried on magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The material thus obtained was purified by column chromatography on silica gel (eluted with 60% ethyl acetate in petroleum ether) to obtain the title compound as a pale yellow solid (8.1 g). LCMS:247(M+1)

[0384] Step C: Preparation of 3-chloro-4-[5-[(2-fluoro-6-nitrophenyl)amino]-1,3-dimethyl-1H-pyrazole-4-yl]benzonitrile To a mixture of 4-(5-amino-1,3-dimethyl-1H-pyrazole-4-yl)-3-chlorobenzonitrile (i.e., the product of step B) (1.2 g, 4.8 mol) in tetrahydrofuran (40 mL), potassium tert-butoxide (9.7 mL, 1 M in tetrahydrofuran) was added dropwise at 0°C. The reaction mixture was stirred at 0°C for 1 hour, then 1,2-difluoro-3-nitrobenzene (0.85 g, 5.3 mmol) was added dropwise, and stirring was continued at 0°C for a further 30 minutes. The reaction mixture was diluted with saturated ammonium chloride aqueous solution and ethyl acetate (100 mL), and the layers were separated. The aqueous layer was extracted with ethyl acetate (40 mL x 2), the combined organic extract was washed with saturated sodium chloride aqueous solution, dried on magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The material thus obtained was purified by column chromatography on silica gel (eluted with 40% ethyl acetate in petroleum ether) to obtain a yellow solid. The yellow solid was crystallized from ethanol to obtain the title compound, which is the compound of the present invention, as a pale yellow solid (560 mg). 1 H NMR(CDCl3)δ 8.71(d,1H),7.85(d,1H),7.63-7.58(m,2H),7.33-7.25(m,2H),6.86-6.82(m,1H),3.75(s,3H),1.99(s,3H). LCMS:386(M+1).

[0385] The compounds disclosed in the table below can be prepared by the procedures described herein, along with methods known in the art. The following abbreviations are used in the table below: Me means methyl, MeO means methoxy, EtO means ethoxy, and CN means cyano.

[0386] [Table 1]

[0387] This disclosure also includes Tables 1A to 46A, each of which is a column header in Table 1 (i.e., "R 2It is CH3, and R 3 is Cl, and (R 4 ) m It is structured the same as Table 1 above, except that "4-F" is replaced with the headings of the respective columns shown below.

[0388] [Table 2]

[0389] [Table 3]

[0390] Formulation / Practical Application A compound of Formula 1 of the present invention (including its N-oxide and salt) or a mixture (i.e., a composition) comprising the compound and at least one additional bactericidal compound described in the abstract of the invention will generally be used as a bactericidal active ingredient in a composition, i.e., a formulation, together with at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents that function as a carrier. The formulation or composition component will depend on the physical properties of the active ingredient and the form of application. Furthermore, it is selected to match environmental factors such as soil type, moisture content, and temperature.

[0391] A mixture of component (a) (i.e., at least one compound of formula 1, its N-oxide or salt) and component (b) (e.g., selected from (b1) to (b54) above and its salts) and / or one or more other biologically active compounds or agents (i.e., insecticides, other fungicides, nematicides, acaricides, herbicides and other bioagents) can be formulated in many ways, including the following: (i) Component (a), component (b) and / or one or more other biologically active compounds or agents may be formulated separately and applied separately, or may be applied simultaneously in an appropriate weight ratio, for example, as a tank mix, or (ii) Components (a), (b), and / or one or more other biologically active compounds or agents may be combined in appropriate weight ratios.

[0392] Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifying concentrates), suspensions, and emulsions (including microemulsions, oil-in-water emulsions, fluid concentrates, and / or suspendemulsions), which can optionally be concentrated into gels. Common types of aqueous liquid compositions include soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, microemulsions, oil-in-water emulsions, fluid concentrates, and suspendemulsions. Common types of non-aqueous liquid compositions include emulsifying concentrates, microemulsifying concentrates, dispersible concentrates, and oil dispersions.

[0393] Common types of solid compositions include dust, powder, granules, pellets, prills, pastyls, tablets, and filling films (including seed coatings), which may be water-dispersible ("wettable") or water-soluble. Films and coatings formed from film-forming solutions or fluid suspensions are particularly useful for seed treatment. Active ingredients can be (micro)encapsulated and further formed into suspensions or solid formulations. Alternatively, the entire active ingredient formulation can be encapsulated (or "overcoated"). Encapsulation allows for control or delaying the release of the active ingredient. Emulsified granules combine the advantages of both emulsified concentrate formulations and dry granular formulations. High-strength compositions are primarily used as intermediates for further formulations.

[0394] Of particular note is an embodiment of a composition in which granules of a solid composition containing the compound of Formula 1 (or its N-oxide or salt) are mixed with granules of a solid composition containing component (b). These mixtures can be further mixed with granules containing additional agricultural protective agents. Alternatively, two or more agricultural protective agents (e.g., component (a) the compound of Formula 1, component (b) the compound, or agricultural protective agents other than component (a) or (b)) can be combined in a set of granular solid compositions, which can then be mixed with one or more sets of granules of solid compositions containing one or more additional agricultural protective agents. These granular mixtures can conform to the disclosure of general granular mixtures in the PCT Patent Publication, the International Publication No. 94 / 24861 brochure, or more preferably the teaching of homogeneous granular mixtures in U.S. Patent No. 6,022,552.

[0395] Sprayable formulations are typically spread in a suitable medium before spraying. Such liquid and solid formulations are formulated to be easily diluted in a spray medium, usually water, but sometimes other suitable mediums such as aromatic or paraffinic hydrocarbons or vegetable oils. Spray volumes can range from approximately 1 to several thousand liters per hectare, but more typically from approximately 10 to several hundred liters per hectare. Sprayable formulations can be tank-mixed with water or other suitable media for foliar treatment or application to plant growth media via aerial or ground application. Liquid and dry formulations can be injected directly into drip irrigation systems or into furrows at planting time. Liquid and solid formulations are used on crops and It can be applied as a seed treatment to seeds of other desirable vegetation before planting, protecting the growing roots and other underground plant parts and / or leaves through systemic absorption.

[0396] The formulation will typically contain active ingredients, diluents, and surfactants within the following approximate ranges, added to 100 weight percent.

[0397] [Table 4]

[0398] Examples of solid diluents include clay, such as bentonite, montmorillonite, attapulgite, kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate, and sodium bicarbonate and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.

[0399] Examples of liquid diluents include water, N,N-dimethylalkaneamide (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidone (e.g., N-methylpyrrolidinone), alkyl phosphate (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffin (e.g., white mineral oil, normal paraffin, isoparaffin), alkylbenzene, alkylnaphthalene, glycerin, glycerin triacetate, sorbitol, aromatic hydrocarbons, dearomatic aliphatic hydrocarbons, alkylbenzenes, alkylnaphthalenes, ketones, such as cyclohexanone, 2-heptanone, isophorone, and 4-hydroxy-4-methyl-2-phenyl Examples include ethanol, acetates such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters such as alkylated lactic acid esters, dibasic esters, alkyl and aryl benzoates and γ-butyrolactone, and alcohols that may be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, cresol and benzyl alcohol. Liquid diluents include saturated and unsaturated fatty acids (typically C6-C6). 22Liquid diluents also include glycerol esters of plant seeds and fruit oils (e.g., olive, castor, flaxseed, sesame, corn, peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut, and palm kernel oils), animal fats (e.g., beef tallow, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, and butylated), where the fatty acids can be obtained by hydrolysis of glycerol esters from plant and animal sources and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.

[0400] The solid and liquid compositions of the present invention often contain one or more surfactants. Surfactants (also known as "surface surfactants"), when added to a liquid, generally alter, and most often reduce, the surface tension of the liquid. Due to the hydrophilic and lipophilic properties of the surfactant molecules, surfactants can be useful as wetting agents, dispersants, emulsifiers, or defoamers.

[0401] Surfactants are classified as nonionic, anionic, or cationic. Nonionic surfactants useful for this composition include, but are not limited to, alcohol alkoxylates, e.g., alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from alcohol and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof; amine estoxylates, alkanolamides, and ethoxylated alkanolamides; alkoxylated triglycerides, e.g., ethoxylated soybean oil, castor oil, and rapeseed oil; alkylphenol alkoxylates, e.g., octylphenol ethoxylate, nonylphenol ethoxylate, dinonylphenol ethoxylate, and dodecylphenol ethoxylate (prepared from phenol and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide, and reverse block polymers in which the terminal blocks are prepared from propylene oxide. Copolymers; ethoxylated fatty acids; ethoxylated fatty acid esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenol (including those prepared from ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); fatty acid esters, glycerol esters, lanolin-based derivatives, polyethoxylate esters, such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitan fatty acid esters and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives such as sorbitan esters; polymer-based surfactants such as random copolymers, block copolymers, alkyl PEG (polyethylene glycol) resins, graft polymers or comb polymers and star polymers; polyethylene glycol (PEG); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar derivatives, such as sucrose esters, alkyl polyglycosides; and alkyl polysaccharides.

[0402] Useful anionic surfactants include, but are not limited to, alkylaryl sulfonic acids and their salts; carboxylated alcohols or alkylphenol ethoxylates; diphenyl sulfonic acid derivatives; lignin and lignosulfonates and other lignin derivatives; maleic acid or succinic acid or their anhydrides; phosphate esters such as olefin sulfonates, alcohol alkoxylates, alkylphenol alkoxylates, and styrylphenol ethoxylates; protein-based surfactants; sarcosine derivatives; styrylphenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols Examples include phosphates; sulfonates of amines and amides such as N,N-alkyl taurates; sulfonates of benzene, cumene, toluene, xylene, and dodecyl and tridecylbenzene; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkylnaphthalenes; sulfonates of fractionally distilled petroleum; sulfosuccinates; and sulfosuccinates and their derivatives, such as dialkyl sulfosuccinate salts.

[0403] Useful cationic surfactants include, but are not limited to, amides and ethoxylated amides; amines such as N-alkylpropanediamine, trippropyltriamine and dipropylenetetramine; ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxide and bis-(2-hydroxyethyl)-alkylamine oxide.

[0404] Furthermore, useful components of the present invention include mixtures of nonionic surfactants and anionic surfactants, or mixtures of nonionic surfactants and cationic surfactants. Nonionic, anionic, and cationic surfactants, as well as their recommended uses, are disclosed in various published literature, including McCutcheon's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.

[0405] The compositions of the present invention may also contain formulation aids and additives known to those skilled in the art as formulation auxiliaries. Such formulation aids and additives can control pH (buffering agents), foaming during processing (antifoaming agents such as polyorganosiloxanes (e.g., Rhodorsil® 416)), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), microbial growth in containers (antimicrobial agents), product freezing (antifreeze agents), color (dye / pigment dispersions (e.g., Rhodorsil® Colorant Red)), washability (film-forming agents or stickers), evaporation (evaporation retarders), and other formulation properties. Examples of film-forming agents include polyvinyl acetate, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers, and waxes. Examples of compounding aids and additives are listed in McCutcheon's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co., and in the PCT publication, International Publication No. 03 / 024222.

[0406] The compound of Formula 1 and any other active ingredients are typically incorporated into the composition by dissolving the active ingredient in a solvent or by grinding it in a liquid or dry diluent. Solutions containing emulsifiable concentrates can be prepared simply by mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is not miscible with water, Emulsifiers are typically added to emulsify the active solvent when diluting with water. Active ingredient slurries with a maximum particle size of 2,000 μm can be wet-milled using a media mill to obtain particles with an average particle size of less than 3 μm. Aqueous slurries can be made into a finished suspension concentrate (see, for example, U.S. Patent No. 3,060,084) or further treated by spray-drying to form water-dispersible granules. Dry formulations typically require a dry-milling process to produce an average particle size in the range of 2 to 10 μm. Dust and powders can be prepared by blending and usually by milling (e.g., hammer mill or fluid energy mill). Granules and pellets can be prepared by spraying the active substance onto a pre-formed granular carrier or by flocculation techniques. See Browning, "Agglomeration," Chemical Engineering, December 4, 1967, pp. 147-148; Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pp. 8-57 et seq.; and International Publication No. 91 / 13546. Pellets can be prepared as described in U.S. Patent No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Patent No. 4,144,050, U.S. Patent No. 3,920,442 and German Patent No. 3,246,493. Tablets can be prepared as taught in U.S. Patent No. 5,180,587, U.S. Patent No. 5,232,701 and U.S. Patent No. 5,208,030. The film can be prepared as taught in British Patent No. 2,095,558 and U.S. Patent No. 3,299,566.

[0407] One embodiment of the present invention relates to a method for controlling fungal pathogens, comprising diluting a bactericidal composition of the present invention (a compound of Formula 1 formulated with a surfactant, a solid diluent, and a liquid diluent, or a mixture of a compound of Formula 1 and at least one other bactericidal agent) with water, optionally adding an adjuvant to form a diluted composition, and contacting a fungal pathogen or its environment with an effective amount of the diluted composition.

[0408] A spray composition formed by diluting a sufficiently concentrated bactericidal composition of the present invention with water exhibits sufficient efficacy in controlling fungal pathogens, but it is also possible to add separately formulated adjuvant products to the spray tank mixture. These additional adjuvants are generally known as “spray adjuvants” or “tank-mixed adjuvants” and include any substance mixed in the spray tank to improve the performance of the pesticide or to alter the physical properties of the spray mixture. Adjuvants may be anionic or nonionic surfactants, emulsifiers, petroleum-based crop oils, crop-derived seed oils, acidifiers, buffers, thickeners, or defoamers. Adjuvants are used to improve efficacy (e.g., bioavailability, adhesion, penetration, uniformity of coverage, and durability of protection) or to minimize or eliminate spray problems related to incompatibility, foaming, drift, evaporation, volatilization, and decomposition. To obtain optimal performance, adjuvants are selected with respect to the characteristics of the active ingredient, formulation, and target (e.g., crops, pests).

[0409] The amount of adjuvant added to the spray mixture is generally in the range of approximately 2.5% to 0.1% by volume. The application rate of adjuvant added to the spray mixture is generally about 1 to 5 liters per hectare. Typical examples of spray adjuvants include Adigor® (Syngenta) 47% methylated rapeseed oil liquid hydrocarbon, Silwet® (Helena Chemical Company) polyalkylene oxide-modified heptamethyltrisiloxane, and Assist® (BASF) 83% paraffin-based mineral oil with 17% surfactant blend.

[0410] One method of seed treatment involves applying the compound of the present invention (i.e., the compound) before sowing the seeds. The coating is applied by spraying or dusting the seeds (as a finished product). Compositions formulated for seed treatment generally contain film-forming agents or adhesives. Therefore, typically, the seed coating compositions of the present invention contain a biologically effective amount of the compound of Formula 1 and a film-forming agent or adhesive. Seeds can be coated by spraying a fluid suspension concentrate directly onto a seed tumbling bed and then drying the seeds. Alternatively, other formulation types such as wet powders, solutions, suspend emulsions, emulsifying concentrates, and aqueous emulsions can be sprayed onto the seeds. This process is particularly useful for the application of film coating to seeds. Various coating machines and processes are available to those skilled in the art. Suitable processes include those described in P. Kosters et al., Seed Treatment: Progress and Prospects, 1994 BCPC Mongraph No. 57 and the references cited therein.

[0411] For further information on formulation technology, see T.Swoods, "The Formulator's Toolbox - Product Forms for Modern Agriculture," in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. Roberts, Eds, Proceedings of the 9th International Congress on See Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. Also, U.S. Patent No. 3,235,361, paragraph 6, lines 16-7, line 19 and Examples 10-41; U.S. Patent No. 3,309,192, paragraph 5, lines 43-7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Patent No. 2,891,855, paragraph 3, lines 66-5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp. 81-96; Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB See also Publications, Richmond, UK, 2000.

[0412] In the following examples, all percentages are by weight, and all formulations are prepared by conventional methods. Compound numbers refer to compounds in index tables A and B. Without further detail, those skilled in the art using the foregoing description will be able to utilize the present invention to its most complete degree. Therefore, the following examples are provided merely as illustrations and are not intended to limit the present disclosure in any way.

[0413] Example A high strength concentrate Compound 60 98.5% Silica Aerogel 0.5% Synthetic amorphous fine silica 1.0%

[0414] Example B Wettable powder Compound 68 65.0% Dodecylphenol polyethylene glycol ether 2.0% Sodium lignin sulfonate 4.0% Sodium aluminosilicate 6.0% Montmorillonite (calcined) 23.0%

[0415] Example C Granules Compound 72 10.0% Attapulgite granules (low volatility, 0.71 / 0.30 mm; USS No. 25-50 sieve) 90.0%

[0416] Example D Extruded pellets Compound 93 25.0% Anhydrous sodium sulfate 10.0% Crude calcium lignin sulfonate 5.0% Sodium alkylnaphthalene sulfonate 1.0% Calcium / Magnesium Bentonite 59.0%

[0417] Example E emulsifiable concentrate Compound 112 10.0% Polyoxyethylene sorbitol hexaoleate 20.0% C6~C 10 Fatty acid methyl ester 70.0%

[0418] Example F Microemulsion Compound 118 5.0% Polyvinylpyrrolidone-vinyl acetate copolymer 30.0% Alkyl polyglycoside 30.0% Glyceryl monooleate 15.0% Water 20.0%

[0419] Example G Seed treatment Compound 60 20.00% Polyvinylpyrrolidone-vinyl acetate copolymer 5.00% Montane wax 5.00% Calcium lignin sulfonate 1.00% Polyoxyethylene / polyoxypropylene block copolymer 1.00% Stearyl alcohol (POE2O) 2.00% Polyorganosilane 0.20% Coloring agent: Red dye 0.05% Water 65.75%

[0420] Example H Fertilizer sticks Compound 68 2.50% Pyrrolidone-styrene copolymer 4.80% Tristyrylphenyl 16-ethoxylate 2.30% Talc 0.80% Corn starch 5.00% Sustained-release fertilizer 36.00% Kaolin 38.00% Water 10.60%

[0421] Example I Suspension concentrate Compound 72 35% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone-based defoaming agent 0.1% 1,2-Benzisothiazolin-3-one 0.1% Water 53.7%

[0422] Example J Emulsion in water Compound 93 10.0% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone-based defoaming agent 0.1% 1,2-Benzisothiazolin-3-one 0.1% Aromatic petroleum-based hydrocarbons 20.0 Water 58.7%

[0423] Example K oil dispersion Compound 112 25% Polyoxyethylene sorbitol hexaoleate 15% Organically modified bentonite clay 2.5% Fatty acid methyl ester 57.5%

[0424] Example L Suspension emulsion Compound 118 10.0% Imidaclopride 5.0% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone-based defoaming agent 0.1% 1,2-Benzisothiazolin-3-one 0.1% Aromatic petroleum-based hydrocarbons 20.0% Water 53.7%

[0425] Water-soluble and water-dispersible formulations are typically diluted with water before application to form aqueous compositions. Aqueous compositions for direct application to plants or parts thereof (e.g., spray tank compositions) typically contain at least about 1 ppm (e.g., 1 ppm to 100 ppm) of the compound of the present invention.

[0426] Seeds are typically treated at a rate of approximately 0.001 g (more typically about 0.1 g) to 10 g per kg of seed (i.e., about 0.0001 to 1% by weight of the seed before treatment). The fluid suspension formulated for seed treatment typically contains about 0.5 to 70% active ingredients, about 0.5 to 30% film-forming adhesives, about 0.5 to 20% dispersants, about 0 to 5% thickeners, 0 to 5% pigments and / or dyes, 0 to 2% defoamers, 0 to 1% preservatives, and 0 to 75% volatile liquid diluents.

[0427] The compounds of the present invention are useful as plant disease control agents. Therefore, the present invention further includes a method for controlling plant diseases caused by fungal plant pathogens, comprising applying an effective amount of the compound of the present invention or a fungicidal composition containing the compound to a protected plant or part thereof, or to a protected plant seed. The compounds and / or compositions of the present invention provide control of diseases caused by a wide range of fungal plant pathogens, including Ascomycota, Basidiomycota, Zygomycota, and fungal-like Oomycota. These are effective in controlling a wide range of plant diseases, particularly leaf pathogens of ornamental, turf, vegetable, field, grain, and fruit crops. These pathogens include, but are not limited to, those shown in Table 1-1. For Ascomycota and Basidiomycota, both the sexual / teleomorph / complete stage names and the asexual / anamorph / incomplete stage names (in parentheses) are given where known. Synonyms for pathogens are indicated with an equals sign. For example, the name of the sexual / teleomorph / perfect stage, Phaeoshaeria nodorum, is followed by the name of the corresponding asexual / anamorph / incomplete stage, Stagonospora nodorum, and the older synonym, Septoria nodorum.

[0428] [Table 5]

[0429] [Table 6]

[0430] In addition to bactericidal activity, the composition or combination also possesses activity against bacteria such as Erwinia amylovora, Xanthomonas campestris, Pseudomonas syringae, and other related species. By controlling harmful microorganisms, the compounds of the present invention are useful for improving (i.e., increasing) the ratio of beneficial microorganisms to harmful microorganisms in contact with crop plants or their reproductive bodies (e.g., seeds, corms, bulbs, tubers, cuttings) or the agricultural environment in which crop plants or their reproductive bodies come into contact.

[0431] The compounds of the present invention are useful for treating all plants, plant parts, and seeds. Plant and seed varieties and cultivars can be obtained by conventional propagation and breeding methods or by genetic engineering methods. Genetically modified plants or seeds (genetically modified plants or seeds) are those in which a different gene (introduced gene) has been stably incorporated into the genome of a plant or seed. An introduced gene, defined by its specific location within the plant genome, is called a transformation or transformation event. Bu.

[0432] Genetically modified plant cultivars that can be treated according to the present invention include those that are resistant to one or more biological stresses (pests such as nematodes, insects, mites, and fungi) or abiotic stresses (such as drought, low temperatures, and soil salinity), or that possess other desirable characteristics. Plants can be genetically modified to exhibit, for example, herbicide resistance, insect resistance, an improved oil profile, or drought resistance.

[0433] By treating genetically modified plants and seeds with the compounds of the present invention, super-additive or enhanced effects can be obtained. For example, a decrease in application rate, an expansion of the activity spectrum, increased resistance to biological / non-biological stress, or improved storage stability may be greater than what would be expected from a simple additive effect by applying the compounds of the present invention to genetically modified plants and seeds.

[0434] The compounds and compositions of the present invention are useful for seed treatment to protect seeds from plant diseases. With respect to this disclosure and claims, seed treatment means contacting seeds with a biologically effective amount of the compounds of the present invention, typically formulated as a composition of the present invention. This seed treatment protects seeds from soilborne pathogens and generally protects the roots and other plant parts that come into contact with the soil of seedlings developing from germinated seeds. This seed treatment can also provide foliar protection through the translocation of the compounds of the present invention or a second active ingredient within the developing plant. Seed treatment can be applied to all types of seeds, including seeds from plants that have been genetically transformed to express specific characteristics. Typical examples include those that express proteins toxic to invertebrate pests such as Bacillus thuringiensis toxin, or those that express herbicide resistance, such as glyphosate acetyltransferase, which provides resistance to glyphosate. Furthermore, seed treatment with the compounds of the present invention can increase the vitality of plants growing from seeds.

[0435] The compounds and compositions of the present invention, used alone or in combination with other fungicides, nematicides, and insecticides, are not limited to those described herein but are particularly useful in seed treatment for crops including corn or corn, soybeans, cotton, cereals (e.g., wheat, oats, barley, rye, and rice), potatoes, vegetables, and rapeseed.

[0436] Furthermore, the compounds of the present invention are useful for treating post-harvest diseases of fruits and vegetables caused by fungi and bacteria. These infections can occur before, during, and after harvest. For example, infection may occur before harvest and remain dormant until some point during ripening (e.g., the host begins to alter its tissues in a way that allows the infection to progress); or infection may arise from surface damage caused by machinery or insect pests. In this regard, the compounds of the present invention can reduce losses due to post-harvest diseases (i.e., losses due to quantity and quality) that may occur at any time between harvest and consumption. Treatment of post-harvest diseases with the compounds of the present invention can increase the period during which fresh edible plant parts (e.g., fruits, seeds, leaves, stems, bulbs, tubers) can be stored refrigerated or unrefrigerated after harvest, remain edible, and are free from significant or harmful deterioration or contamination by fungi or other microorganisms. Treatment of edible plant parts before or after harvest with the compounds of the present invention can also reduce the production of toxic metabolites of fungi or other microorganisms, such as mycotoxins, including aflatoxins.

[0437] Plant disease control is usually achieved by applying an effective amount of the compound of the present invention to the part of the plant to be protected, such as roots, stems, leaves, fruits, seeds, tubers, or bulbs, or to the growing medium (soil or sand) in which the plant is growing, either before or after infection. The compounds can also be applied to seeds to protect the seeds and seedlings that develop from them. The compounds can also be applied to treat plants through irrigation water. Control of post-harvest pathogens that infect crops before harvest is typically achieved by field application of the compounds of the present invention, and if infection occurs after harvest, the compounds can be applied to harvested crops as dips, sprays, fumigants, treatment wraps, and box liners.

[0438] The compounds can also be applied using unmanned aerial vehicles (UAVs) to disperse the compositions disclosed herein over a planting area. In some embodiments, the planting area is an area containing crops. In some embodiments, the crops are selected from monocots or dicots. In some embodiments, the crops are selected from rice, maize, barley, buckwheat, wheat, vegetables, tobacco, tea plants, fruit trees, and sugarcane. In some embodiments, the compositions disclosed herein are formulated for spraying at ultra-low volumes. Products applied by drones can use water or oil as a spray carrier. Typical spray volumes (including products) used globally for drone applications range from 5.0 liters / hectare to 100 liters / hectare (approximately 0.5 to 10 gpa). This includes the range from ultra-low spray volumes (ULV) to low spray volumes (LV). Less common, however, there may be situations where even lower spray volumes, such as 1.0 liter / ha (0.1 gpa), are used.

[0439] The appropriate application rate (e.g., effective fungicide amount) of component (a) (i.e., at least one compound selected from the compounds of Formula 1, its N-oxides, and salts) and the appropriate application rate (e.g., biologically effective amount, fungicidal effective amount, or insecticidal effective amount) of mixtures and compositions containing component (a) according to the present invention should be determined under actual usage conditions, influenced by factors such as the plant disease being controlled, the plant species being protected, the population structure of the pathogen being controlled, ambient moisture and temperature, etc. Those skilled in the art can easily determine the effective fungicidal amount required for the desired level of plant disease control by simple experiments. Leaves can usually be protected when treated with rates of active ingredient ranging from less than about 1 g / ha to about 5,000 g / ha. Seeds and seedlings can usually be protected when treated with rates ranging from about 0.001 g (more typically about 0.1 g) to about 10 g per kg of seed. Those skilled in the art can easily determine, by simple experiments, the application rates of components (a) and mixtures and compositions containing specific combinations of the active ingredients according to the present invention necessary to provide a desired range of plant protection and control of plant diseases and, optionally, other plant pests.

[0440] The compounds and compositions of the present invention may also be useful for increasing the vitality of crop plants. The method involves contacting a crop plant (e.g., leaves, flowers, fruits, or roots) or a seed on which a crop plant is growing with a composition containing a sufficient amount (i.e., a biologically effective amount) of the compound of Formula 1 to achieve a desired plant vitality effect. Typically, the compound of Formula 1 is applied in a formulated composition. The compound of Formula 1 is often applied directly to the crop plant or its seed, but it can also be applied to the location of the crop plant, i.e., the environment of the crop plant, in particular a part of the environment that is close enough for the compound of Formula 1 to be transferred to the crop plant. The location relevant to this method most commonly includes the growing medium on which the plant is cultivated (i.e., the medium that supplies nutrients to the plant), typically soil. Therefore, the treatment of crop plants to increase their vitality involves contacting the crop plant, the seed on which the crop plant is growing, or the location of the crop plant with a biologically effective amount of the compound of Formula 1.

[0441] Increased crop vitality can result in one or more of the following observed effects: (a) optimal crop growth, indicated by superior seed germination, crop emergence, and crop stand; (b) improved crop growth, indicated by rapid and robust leaf growth (e.g., measured by leaf area index), plant height, number of tillers (e.g., in the case of rice), root mass, and total dry weight of the growing portion of the crop; (c) time to flowering, flowering period, number of flowers, total (d) improved crop yields, indicated by biomass accumulation (i.e., yield) and / or marketability (i.e., yield quality) of the fruit or grain grade of the produce; (f) improved ability of crops to be resistant to or prevent infection by plant diseases and arthropod, nematode or mollusk pests; and (e) improved ability of crops to be resistant to environmental stresses such as exposure to extreme temperatures, suboptimal moisture or phytotoxic chemicals.

[0442] The compounds and compositions of the present invention can increase the vitality of treated plants compared to untreated plants by preventing and / or curing plant diseases caused by fungal plant pathogens in the plant environment. Without control of such plant diseases, the diseases reduce plant vitality by consuming plant tissue or sap, or by transmitting plant pathogens such as viruses. Even in the absence of fungal plant pathogens, the compounds of the present invention can increase plant vitality by altering plant metabolism. Generally, the vitality of crop plants will increase most significantly by treating them with the compounds of the present invention when the plants are grown in a non-ideal environment, i.e., an environment that includes one or more aspects unfavorable to achieving the full genetic potential that the plants would exhibit in an ideal environment.

[0443] Of particular interest are methods for increasing the vitality of crop plants growing in environments containing plant diseases caused by fungal plant pathogens. Methods for increasing the vitality of crop plants growing in environments free from plant diseases caused by fungal plant pathogens are also noteworthy. Furthermore, methods for increasing the vitality of crop plants growing in environments containing amounts of moisture that are not ideal for supporting their growth are also of interest.

[0444] The compounds and compositions of the present invention can be mixed with fungicides, insecticides, nematicides, fungicides, acaricides, herbicides, herbicide detoxifiers, growth regulators, such as insect molting inhibitors and rooting promoters, chemical hemostatic agents, semi-chemical substances, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds, or one or more other biologically active compounds or agents, including entomopathogenic bacteria, viruses, or fungi, to form multi-component insecticides that provide an even broader spectrum of agricultural protection. Accordingly, the present invention also relates to compositions comprising (a fungicidally effective amount) of the compound of Formula 1 and (a biologically effective amount) at least one additional biologically active compound or agent, which may further comprise at least one of a surfactant, a solid diluent, or a liquid diluent. Other biologically active compounds or agents can be incorporated into compositions comprising at least one of a surfactant, a solid diluent, or a liquid diluent. With respect to the mixture of the present invention, one or more other biologically active compounds or agents can be combined with the compound of Formula 1 to form a premix, or one or more other biologically active compounds or agents can be combined separately from the compound of Formula 1, and the mixture can be combined before application (for example, in a spray tank) or applied sequentially instead.

[0445] As described in the summary of the invention, one aspect of the present invention is a bactericidal composition (i.e., mixture or combination) comprising a compound of formula 1, its N-oxide or salt (i.e., component a) and at least one other bactericide (i.e., component b). Of note is such a combination in which the other bactericidal active ingredient has a different site of action than the compound of formula 1. In certain examples, a combination with at least one other bactericidal active ingredient having a similar control spectrum but a different site of action is particularly advantageous for resistance control. Accordingly, the composition of the present invention may further contain a bactericidal effective amount of at least one additional bactericidal active ingredient having a similar control spectrum but a different site of action.

[0446] Examples of ingredients (B) fungicides include acibenzolar-S-methyl, algimorph, ametocrazine, amisulbrom, anilazine, azaconazole, azoxystrobin, venalaxyl (including venalaxyl-M), benodanil, benomyl, and benciabaricarb (ben). (Containing ciabaricarb-isopropyl), benzovindiflupir, behoxazine, binapacril, biphenyl, vitertanol, bixafen, blastosidine-S, boscalid, bromconazole, bupirimate, butthiovate, captahol, captan, carbendazim, carboxyne, carpropamide, chloroneb, chlorothalonil, clozolinate, clotrimazole, copper hydroxide, copper oxychloride, copper sulfate, chemoxystrobin, cyazofamide, cyflufenaamide, cymoxanil, cyproconazole, cyprodinil, diclofluanide, diclosi Meth, diclomazine, dichlorane, diethofencarb, difenoconazole, diflumethrim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole (including diniconazole-M), dinocap, dithianone, dithiolan, dodemorph, dozin, dipimethitron, econazole, edifenphos, enoxastrobin (also known as enestrobrin), epoxyconazole, etaconazole, etaboxam, esirimol, etridiazole, famoxadone, phenamidon, phenalimol, phenaminestrobin, fenbuconazole, f Fenflam, fenhexamide, phenoxanil, fenpiclonil, fenpropidine, fenpropimorph, fenprirasamine, fentin acetate, fentin chloride, fentin hydroxide, ferubam, ferimzon, flomethkin, florylpicoxamide, fluazinam, fludioxonil, fluphenoxystrobin, fluindapir, flumorph, fluopicolide, fluopimomid, fluopyram, fluuroimide, floxasastrobin, fluquinconazole, flusilazole, flusulfamide, fluthianil, flutolanil, flutriol Lu, fluxapiroxad, Holpet, phthalide, fuberidazole, flaxyl, flamethopir, guazatin, hexaconazole, himexazole, imazalil, imibenconazole, iminoctadine albesylate, iminoctadine triacetate, iodocarb, ipconazole, ipfentrifluconazole, iprobenphos, iprodione, iprovalicarb, isoconazole, isofenamide, isoprothiolane, isoflucipram, isopyrazam, isothianil, kasugamycin, kresoxim-methyl, mancozeb, mandepropamide,Mandestrobin, Maneb, Mepanipyrim, Mepronil, Meptildinocap, Metalaxyl (including Metalaxyl-M / Mephenoxam), Mefentrifluconazole, Meconazole, Metasulfocarb, Methylam, Metrominostrobin, Metraphenone, Miconazole, Mycrobutanil, Naphthifine, Neo-Asodine, Nualimol, Octylinone, Oflars, Orysastrobin, Oxadixyl, Oxatiapiproline, Oxolinic Acid, Oxpoconazole, Oxycarboxyne, Oxytetracycline, Peflazoate, Penco Nazole, Pencyclon, Perflufen, Penthiopyrad, Phosphate (including its salts, e.g., fosetyl-aluminum), Picarbtrazox, Picoxystrobin, Piperalin, Polyoxin, Probenazole, Prochloraz, Procymidone, Propamacarb, Propiconazole, Propineb, Proquinazide, Prothiocarb, Prothioconazole, Pyraclostrobin, Pyramethostrobin, Pyraoxystrobin, Pyrazofos, Pyribencarb, Pyributicarb, Pyriphenox, Pyrimethanil, Pyriophenone, Pyrisoxazole, Pyro Chiron, Pyrrolnitrin, Quinconazole, Quinofumerine (Registration No. 861647-84-9), Quinomethionate, Quinoxyfen, Quintozene, Sedaxane, Silthiofam, Simeconazole, Spiroxamine, Streptomycin, Sulfur, Tebuconazole, Tebufloxin, Tecrophthalam, Technazen, Terbinafine, Tetraconazole, Thiabendazole, Tifluzamide, Thiophanate, Thiophanate-methyl, Thiram, Thiazinyl, Tolcrophos-methyl, Tolniphanide, Tolprocarb, Trifluanide, Triadimephon, To Riadimenol, Trialimol, Triticonazole, Triazoxide, Tribasic copper sulfate, Tricyclazole, Triclopyricarb, Tridemorph, Trifloxystrobin, Triflumizole, Triforine, Trimorphamide, Uniconazole, Uniconazole-P, Validamycin, Valifenarate (also known as Valifena), Vinclozoline, Zineb, Ziram, Zoxamide, N-[2-(1S,2R)-[1,1'-Bicyclopropyl]-2-ylphenyl]-3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,α-(1-chlorocyclopropyl)-α-[2-(, [2,2-Dichlorocyclopropyl)ethyl]-1H-1,2,4-triazole-1-ethanol, (αS)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-4-isoxazolyl]-3-pyridineemethanol, rel-1-[[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-2-oxyranyl]methyl]-1H-1,2,4-triazole, rel-2-[[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-2-oxyranyl N-[2-[4-[[3-(4-chlorophenyl)-2-propylinyl]ethyl]-3-methyl-1,2-dihydro-3H-1,2,4-triazole-3-thione, rel-1-[[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-2-oxyranyl]methyl]-5-(2-propen-1-ylthio)-1H-1,2,4-triazole, N-[2-[4-[[3-(4-chlorophenyl)-2-propylinyl-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulfonyl)amino]butanamide, N-[2-[4-[[3-(4-chlorophenyl)-2-propylinyl]methyl] [Ropin-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(ethylsulfonyl)amino]butanamide, N'-[4-[4-chloro-3-(trifluoromethyl)phenoxy]-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide, N-[[(cyclopropylmethoxy)amino][6-(difluoromethoxy)-2,3-difluorophenyl]methylene]benzeneacetamide, N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methylethyl]-3-(difluoromethyl)-1-methyl Lu-1H-pyrazole-4-carboxamide, N-(3',4'-difluoro[1,1'-biphenyl]-2-yl)-3-(trifluoromethyl)-2-pyrazinecarboxamide, 3-(difluoromethyl)-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide, 5,8-difluoro-N-[2-[3-methoxy-4-[[4-(trifluoromethyl)-2-pyridinyl]oxy]phenyl]ethyl]-4-quinazolinamine, 1-[4-[4-[5R-[(2,[6-Difluorophenoxy)methyl]-4,5-Dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperdinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]ethanone, 4-fluorophenyl N-[1-[[[1-(4-cyanophenyl)ethyl]sulfonyl]methyl]propyl]carbamate, 5-fluoro-2-[(4-fluorophenyl)-methoxy]-4-pyrimidineamine, α-(meth Examples include xyimino)-N-methyl-2-[[[1-[3-(trifluoromethyl)phenyl]ethoxy]imino]methyl]benzeneacetamide and [[4-methoxy-2-[[[(3S,7R,8R,9S)-9-methyl-8-(2-methyl-1-oxopropoxy)-2,6-dioxo-7-(phenylmethyl)-1,5-dioxonan-3-yl]amino]carbonyl]-3-pyridinyl]oxy]methyl 2-methylpropanoate. Therefore, of note is a bactericidal composition comprising a compound of formula 1 (or its N-oxide or salt) as component (a) and at least one bactericide selected from the above enumeration as component (b).

[0447] Of particular note are the compounds of Formula 1 (or their N-oxides or salts) (i.e., component (a) in the composition) and aminopyriphen (registration number 1531626-08-0), azoxystrobin, benzovindiflupyr, bixafen, captan, carpropamide, chlorothalonil, copper hydroxide, copper oxychloride, copper sulfate, cymoxanil, cyproconazole, cyprodinil, diclobentiazox (registration number 957144-77-3), diethofencarb, difenoconazole, and dimethomole. Epoxyconazole, etaboxam, phenalimol, fenhexamide, fluazinam, fludioxonil, fluindapir, fluopyram, flucilazole, fluthianil, flutriafol, fluxapyroxad, folpet, ipuflufenoquin (registration number 1314008-27-9), iprodione, isofetamide, isoflucipram, isopyrazam, kresoximmethyl, mancozeb, mandestrobin, meptildinocap, metalaxyl (metalaxyl-M / mefeno (including Xam), mefentrifluconazole, metconazole, metraphenone, methyltetraprole (registration number 1472649-01-6), mycrobutanil, oxathiapiproline, penflufen, penthiopyrad, phosphate (including its salts, e.g., fosetyl-aluminum), picoxystrobin, propiconazole, proquinazide, prothioconazole, pyridaclomethyl (registration number 1358061-55-8), pyraclostrobin, pyrapropoine (registration number 1803108-03-3), pyrimethanil, sedaxane, Spiroxamine, sulfur, tebuconazole, thiophanate-methyl, trifloxystrobin, zoxamide, α-(1-chlorocyclopropyl)-α-[2-(2,2-dichlorocyclopropyl)ethyl]-1H-1,2,4-triazole-1-ethanol, 2-[2-(1-chlorocyclopropyl)-4-(2,2-dichlorocyclopropyl)-2-hydroxybutyl]-1,2-dihydro-3H-1,2,4-triazole-3-thione, N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methylethyl]-3-(diflu Oromethyl)-1-methyl-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide, 1-[4-[4-[5R-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]ethanone, 1,1-dimethylethyl N-[6-[[[[(1-methyl rel-1H-tetrazole-5-yl)phenylmethylene]amino]oxy]methyl]-2-pyridinyl]carbamate, dipimethitrone, 5-fluoro-2-[(4-fluorophenyl)methoxy]-4-pyrimidineamine, 5-fluoro-2-[(4-methylphenyl)methoxy]-4-pyrimidineamine, (αS)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-4-isoxazolyl]-3-pyridinemethanol, rel-1-[[(2R,3S)-3-(2-chlorophenyl)-2-(2,The combination is with a component (b) compound selected from 4-difluorophenyl)-2-oxyranyl]methyl]-1H-1,2,4-triazole, rel-2-[[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-2-oxyranyl]methyl]-1,2-dihydro-3H-1,2,4-triazole-3-thione and rel-1-[[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-2-oxyranyl]methyl]-5-(2-propene-1-ylthio)-1H-1,2,4-triazole (i.e., as component (b) in the composition).

[0448] Of particular note are the compounds of Formula 1 (or their N-oxides or salts) (i.e., component (a) in the composition) and aminopyriphen (registration number 1531626-08-0), azoxystrobin, benzovindiflupyr, bixafen, captan, carpropamide, chlorothalonil, copper hydroxide, copper oxychloride, copper sulfate, cymoxanil, cyproconazole, cyprodinil, diclobentiazox (registration number 957144-77-3), diethofencarb, difenoconazole, dimethomorph, dipimethitron, epoxyconazole, etaboxam, phenalimol, fenhexamide, fluazinam, fludioxonil, fluindapyr, fluopyram, flusilazole, fluthianil, flutriafol, fluxapyroxad, folpet, ipuflufe Nokin (Registration No. 1314008-27-9), Iprodione, Isofetamide, Isoflucipram, Isopyrazam, Kresoxim-methyl, Mancozeb, Mandestrobin, Meptildinocap, Metalaxyl (containing Metalaxyl-M / Mephenoxam), Mefentrifluconazole, Metoconazole, Metraphenone, Methyltetraprole (Registration No. 1472649-01-6), Mycrobutanil, Oxatiapiproline, Penflufen, Penthiopyrad, Phosphorous acid (including its salts, e.g., Fosetyl-aluminum), Picoxystrobin, Propiconazole, Proquinazide, Prothioconazole, Pyridaclomethyl (Registration No. 1358061-55-8), Pyraclostrobin, Pyrapropoin (Registration No. 1803108-03-3), Pyrim Tanyl, sedaxane, spiloxamine, sulfur, tebuconazole, thiophanate-methyl, trifloxystrobin, zoxamide, α-(1-chlorocyclopropyl)-α-[2-(2,2-dichlorocyclopropyl)ethyl]-1H-1,2,4-triazole-1-ethanol, N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methylethyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-N-(2,3 -Dihydro-1,1,3-trimethyl-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide, 1-[4-[4-[5R-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]ethanone, 1,1-dimethylethyl N-[6-[[[[(1-methyl-1H-tetrazol-5-yl)phenylmethylene]amino ]oxymethyl]-2-pyridinyl]carbamate, 5-fluoro-2-[(4-fluorophenyl)methoxy]-4-pyrimidineamine, (αS)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-4-isoxazolyl]-3-pyridinemethanol, rel-1-[[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-2-oxyranyl]methyl]-1H-1,2,4-triazole, rel-2-[[(2 The combination is with a component (b) compound selected from R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-2-oxyranyl]methyl]-1,2-dihydro-3H-1,2,4-triazole-3-thione and rel-1-[[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-2-oxyranyl]methyl]-5-(2-propene-1-ylthio)-1H-1,2,4-triazole (i.e., as component (b) in the composition).

[0449] Generally, preferred for better control (e.g., lower usage rates or a wider range of controllable plant pathogens) or resistance management of plant diseases caused by fungal plant pathogens are compounds of Formula 1, their N-oxides or salts, and amisulbrom, azoxystrobin, benzovindiflupyr, bixafen, boscalid, carbendazim, carboxyne, chlorothalonil, copper hydroxide, cymoxanil, cyproconazole, difenoconazole, dimetamorph, dimoxystrobin, epoxyconazole, fenpropidine, fenpropimorph, florylpicoxamide, fluazinam, fludioxonil, fluphenoxystrobin, fluindapyr, fluquinconazole, and flupicolide. It is a mixture with a bactericidal compound selected from the group consisting of fluoxastrobin, flutriafole, fluxapyroxad, ipuconazole, ipufentrifluconazole, iprodione, kresoxim-methyl, mancozeb, metalaxyl, mephenoxam, mefentrifluconazole, metconazole, metminostrobin, mycrobutanil, paclobutrazol, penflufen, picoxystrobin, prothioconazole, pidflumetofen, pyraclostrobin, pyrametostrobin, pyroxystrobin, pyriophenone, sedaxane, silthiofam, tebuconazole, thiabendazole, thiophanate-methyl, thyram, trifloxystrobin, and triticonazole.

[0450] In the bactericidal composition of the present invention, component (a) (i.e., at least one compound selected from the compounds of formula 1, its N-oxide and salts) and component (b) are present in bactericidally effective amounts. The weight ratio of component (b) (i.e., one or more additional bactericidal compounds) to component (a) is generally about 1:3000 to about 3000:1, more typically about 1:500 to about 500:1. Of particular note are compositions in which the weight ratio of component (a) to component (b) is about 125:1 to about 1:125. Of particular note are compositions in which the weight ratio of component (a) to component (b) is about 25:1 to about 1:25 or about 5:1 to about 1:5. Those skilled in the art can determine the weight ratio and application rate of the bactericidal compound required for a desired area of ​​bactericidal protection and control by simple experimental methods. Further bactericidalization in component (b) It is clear that including a compound can expand the range of plant diseases controlled beyond the range controlled by component (a) alone. Furthermore, exemplary weight ratios for combinations of fungicidal compounds of the present invention are provided below in Tables A1-A15 and C1-C15. Table B1 below lists typical, more typical, and most typical ranges of ratios involving specific fungicidal compounds of component (b).

[0451] Table A1 discloses specific mixtures of component (a) compound and component (b) compound. Component (a) compound is identified by its compound number; see Index Tables A-B for a description of the compound. The information under the heading “Exemplary Ratios” discloses three specific weight ratios of component (a) and component (b) for the disclosed mixture. For example, the first row of Table A1 discloses a mixture of compound 1 of the present invention with acibenzolar-S-methyl, where the weight ratio of compound 1 to acibenzolar-S-methyl is 1:1, 1:4, or 1:18.

[0452] [Table 7]

[0453] [Table 8]

[0454] [Table 9]

[0455] [Table 10]

[0456] [Table 11]

[0457] [Table 12]

[0458] [Table 13]

[0459] Tables A2 to A15 are structured the same as Table A1 above, except that the information under the "Component (a)" column heading is replaced with the respective information shown in the Component (a) column below. For example, in Table A2, the information under the "Component (a)" column heading lists all of "Compound 18". Therefore, the first item in Table A2 specifically discloses a mixture of Compound 18 and acibenzolar-S-methyl. Tables A3 to A15 are structured similarly.

[0460] [Table 14]

[0461] Table B1 lists combinations of component (b) compound and component (a) compound illustrating the mixtures, compositions, and methods of the present invention. The first column of Table B1 lists specific component (b) compounds (for example, "acibenzolar-S-methyl" is the first item to be listed). The second, third, and fourth columns of Table B1 list a series of weight ratios of component (b) to component (a) compound, which are typically applied to outdoor-grown crops. Thus, for example, the first row of Table B1 discloses that the combination of component (a) compound and acibenzolar-S-methyl is typically applied in weight ratios of component (a) to component (b) of 2:1 to 1:180, more typically 1:1 to 1:60, and most typically 1:1 to 1:18. The remaining rows of Table B1 are interpreted similarly. Of particular note are the compositions, disclosed in Table B1, which include a mixture of any one of the compounds listed as component (a) in Embodiment 97 and the compounds listed in the component (b) column of Table B1, in the weight ratios disclosed therein. Thus, Table B1 complements the specific ratios disclosed in Tables A1 to A15 with a series of ratios for these combinations.

[0462] [Table 15]

[0463] [Table 16]

[0464] [Table 17]

[0465] [Table 18]

[0466] [Table 19]

[0467] [Table 20]

[0468] [Table 21]

[0469] [Table 22]

[0470] As already noted, the present invention includes embodiments in which the composition comprises components (a) and (b), wherein component (b) comprises at least one bactericidal compound from each of two groups selected from (b1) to (b54). Table C1 lists specific mixtures illustrating embodiments, wherein component (b) comprises at least one bactericidal compound from each of two groups selected from (b1) to (b54). Table C1 discloses mixtures of compound 1 of the present invention with at least two component (b) compounds. The description under the heading “Exemplary Ratios” discloses three specific weight ratios of component (a) to each component (b) compound. For example, the first row discloses a mixture of compound 1 with cyproconazole and azoxystrobin and lists weight ratios of compound 1 with cyproconazole and azoxystrobin of 1:1:1, 2:1:1 or 3:1:1.

[0471] [Table 23]

[0472] [Table 24]

[0473] [Table 25]

[0474] [Table 26]

[0475] [Table 27]

[0476] Tables C2 to C15 are structured the same as Table C1 above, except that the information under the "Component (a)" column heading is replaced with the respective information in the Component (a) column shown below. For example, in Table C2, the information under the "Component (a)" column heading is a complete list of "Compound 18". Therefore, the first item in Table C2 specifically discloses a mixture of Compound 18 with cyproconazole and azoxystrobin, and exemplary weight ratios of Compound 18 with cyproconazole and azoxystrobin are 1:1:1, 2:1:1 and 3:1:1. Tables C3 to C15 are structured similarly.

[0477] [Table 28]

[0478] Of particular note is the composition of the present invention, which comprises the compound of Formula 1 (or its N-oxide or salt) together with at least one other fungicidal compound having a different site of action from the compound of Formula 1. In certain examples, the combination with at least one other fungicidal compound having a similar control spectrum but a different site of action is particularly advantageous with respect to resistance management. Therefore, the composition of the present invention can advantageously contain at least one fungicidal compound selected from the group consisting of (b1) to (b54) above, having a similar control spectrum but a different site of action.

[0479] A composition of component (a) or a composition of component (a) and component (b) can be further mixed with one or more other biologically active compounds or agents, including insecticides, nematicides, fungicides, acaricides, herbicides, herbicide detoxifiers, growth regulators, such as insect molting inhibitors and rooting promoters, chemical hemostatic agents, semi-chemical substances, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds, or entomopathogenic bacteria, viruses, or fungi, to form a multi-component insecticide that provides an even broader spectrum of agricultural protection. Accordingly, the present invention also relates to a composition comprising a bactericidally effective amount of component (a) or a mixture of component (a) and component (b) and a biologically effective amount of at least one additional biologically active compound or agent, which may further comprise at least one of a surfactant, a solid diluent, or a liquid diluent. Other biologically active compounds or agents can also be separately incorporated into a composition comprising at least one of a surfactant, a solid diluent, or a liquid diluent. With respect to the compositions of the present invention, one or more other biologically active compounds or agents can be combined with one or both of components (a) and (b) to form a premix, or one or more other biologically active compounds or agents can be combined separately from components (a) and (b), and the formulations can be combined before application (for example, in a spray tank) or applied sequentially instead.

[0480] Examples of such biologically active compounds or biological agents that can be combined with a composition of component (a) or a composition of component (a) and component (b) include insecticides such as abamectin, acephate, acequinosyl, acetamiprid, acrinatrin, acinonapyr, afidopyropene, amidoflumet, amitraz, avermectin, azadirachtin, azinphosmethyl, benfuracarb, bensultap, benzpyrimoxane, bifenthrin, kappa-bifenthrin, bifena Zete, Bistriflurone, Borate, Brofranilide, Buprofezin, Kazsafos, Carbaryl, Carbofuran, Cartap, Carzol, Chlorantraniliprole, Chlorfenapyr, Chlorfluazurone, Chloroprallethrin, Chlorpyrifos, Chlorpyrifos-e, Chlorpyrifos-methyl, Chromafenozide, Clofentezin, Chloroprallethrin, Clothianidin, Cyantraniliprole, Cyclaniliprole, Cycloprotrin, Cycloxapride, Cyenopyrafe Cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalodiamide, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, diafenthiurone, diazinon, dichloromethothiaz, dierudrin, diflubenzuron, dimefluthrin, dimehypo, dimethoate, zinpropyridaz, dinotefuran, diphenolane, emamectin, emamectin benzoate, endosulfa, esfenvalerate, ethiprole, etofenpro X, epsilon-metoflutrin, etoxazole, fenbutane oxide, fenitrothion, phenothiocarb, phenoxycarb, fenpropathrin, fenvalerate, fipronil, flomethin, flonicamide, fluazaindridin, flubendiamide, flucitrinate, fluphenenelim, flufenoxuron, fluphenoxystrobin, fluensulfone, fluhexaphon, fluopyram, flupiprol, flupyridiflon, flupyrim, fluvalinate, tau-fluvalinate, fluxamethamide, fonofos, holmeta Nate, fothiazate, gamma-cyhalothrin, halophenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, indoxacarb, insecticide soap, isofenphos, isocycloceram, kappatefluthrin, lambda-cyhalothrin, lufenuron, malathion, meperfluthrin, metaflumizone, metaldehyde, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, metofluthrin, methoxyphenozide, epsilon-metofluthrin, epsilon -Monfluorothrin, monoclotophos, monofluorothrin, nicotine, nitenpyram, nithiazine, novaron, nobiflumulon, oxamyl, oxazosulfyl, parathion, parathion-methyl, permethrin, phorate, fosalon, fosmet, phosphamidone, pyrimicab, profenofos, profluthrin, propargit, protrefenbut, piflubmid, pymetrozine, pyrafluprole, pyrethrin, pyridaben, pyridaryl, pyrifluquinazone, pyriminostrobin, pyriproxyfen, rotenone, ryanodine,Silafluofen, spinetoram, spinosad, spirodiclofen, spiromesifen, spiropidione, spirotetramato, sulprofos, sulfoxaflor, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, kappatefluthrin, terbufos, tetrachlorantraniliprole, tetrachlorvinfos, tetramethrin, tetramethylfluthrin, tetraniliprole, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, thioxazafen, tolfenpyrad, tralomethrin, triazamate, trichlorfon, triflumesopyrim, triflumulon, ticlopyrazoflor, zeta-cypermethrin, Bacillus thuringiensis delta-endotoxin, entomopathogenic fungi, entomopathogenic viruses, or entomopathogenic fungi.

[0481] General references for these agricultural protective agents (i.e., insecticides, fungicides, nematicides, acaricides, herbicides, and biopharmaceuticals) include The Pesticide Manual, 13th Edition, CDSTomlin, Ed., British Crop Protection Council, Farnham, Surrey, UK, 2003 and The BioPesticide Manual, 2nd Edition, LGCopping, Ed., British Crop Protection Council, Farnham, Surrey, UK, 2001.

[0482] With respect to embodiments in which one or more of these various mixing partners are used, the weight ratio (total) of these various mixing partners to component (a) or a mixture of component (a) and component (b) is generally about 1:3000 to about 3000:1. Notably, weight ratios of about 1:100 to about 3000:1 or about 1:30 to about 300:1 (e.g., ratios of about 1:1 to about 30:1). By including these additional components, component (a) Alternatively, it will be clear that the spectrum of diseases controlled can be expanded beyond the spectrum controlled by a mixture of component (a) and component (b).

[0483] Compound (a) and / or compound (b) and / or combination thereof with one or more other biologically active compounds or agents can be applied to genetically modified plants that express proteins toxic to invertebrate pests (such as Bacillus thuringiensis delta-endotoxins). The effects of exogenously applied compound (a) alone or in combination with compound (b) of the present invention may be synergistic with the expressed toxic protein.

[0484] Of particular note are the component (a) or combinations or compositions comprising components (a) and (b) as outlined in the abstract of the present invention, further comprising at least one invertebrate pest control compound or agent (e.g., insecticide, acaricide). Of particular note are compositions comprising component (a) and at least one (i.e., one or more) invertebrate pest control compounds or agents, which can then be combined with component (b) to provide a composition comprising components (a) and (b) and one or more invertebrate pest control compounds or agents. Alternatively, a biologically effective amount of a composition comprising component (a) and at least one invertebrate pest control agent can be applied to a plant or plant seed (directly or through the environment of the plant or plant seed) without first mixing with component (b) to protect the plant or plant seed from diseases caused by fungal pathogens and damage caused by invertebrate pests.

[0485] Of particular note are, in addition to the compound (a) alone or in combination with compound (b), abamectin, acetamiprid, acrinatrin, acinonapyr, afidopiropene, amitraz, avermectin, azadirachtin, benfuracarb, bensultap, bifenthrin, buprofezin, brofuranilide, kazusafos, carbaryl, cartap, chlorantraniliprole, chloroprallethrin, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cyfluthrin, beta-cyfluthrin Phosphorus, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, sipapermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, dierdrin, dinotefuran, diofenolan, emamectin, endosulfan, epsilon-metoflutrin, esfenvalerate, ethiprole, etofenprox, etoxazole, fenitrothion, phenothiocarb, phenoxycarb, fenvalerate, fipronil, flomethin, fluxamethamide, flonicamide, flubendiamide, fluen Sulfone, flufenoxuron, fluphenoxystrobin, flufensulfon, flupiprol, flupyrimin, flupyradiflon, fluvalinate, formethaneate, fostiazate, gamma-cyhalothrin, heptafluthrin, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, isocycloserum, capper-tefluthrin, lambda-cyhalothrin, lufenuron, meperfluthrin, metaflumizone, methiodicarb, methomyl, methoprene, methoxyfenozide, mesofluthrin, monofluorothrin, nitenpi Lam, nithiazine, novaron, oxamyl, piflubmid, pymetrozine, pyrethrin, pyridaben, pyridaryl, pyriminostrobin, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulfoxaflor, tebufenozide, tetramethrin, tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, triflumesopyrim, triflumulon, ticlopyrazoflor, zeta-cypermethrin,Bacillus thuringiensis delta-endotoxin, selected from a group consisting of all strains of Bacillus thuringiensis and all strains of nucleopolyhedrosis virus. The present invention comprises at least one invertebrate pest control compound or agent.

[0486] In some cases, a combination of the compound (a) of the present invention, either alone or in a mixture with component (b), and other biologically active (particularly fungicidal) compounds or agents (i.e., active ingredients) can yield an effect greater than the additive effect (i.e., a synergistic effect). It is always desirable to reduce the amount of active ingredients released into the environment while ensuring effective pest control. If the enhancement effect of fungicidal active ingredients occurs at an application rate that provides an agriculturally satisfactory level of fungal control, such combinations can be advantageous in terms of reducing crop production costs and environmental impact.

[0487] Table D1 lists specific combinations of invertebrate pest control agents with compound 1 (compound numbers refer to compounds in index tables A-B) as exemplary component (a) compounds of mixtures and compositions containing these active ingredients according to the present invention, as well as methods of using them. Column 2 of Table D1 lists specific invertebrate pest control agents (e.g., "abamectin" in the first row). Column 3 of Table D1 lists the mechanism of action (if known) or chemical classification of the invertebrate pest control agents. Column 4 of Table D1 describes embodiments of weight ratio ranges for which the invertebrate pest control agent is typically applied to compound 1 alone or in combination with component (b) (e.g., abamectin to compound 1 in weight ratios of "50:1 to 1:50"). Thus, for example, the first row of Table D1 specifically discloses that the combination of compound 1 and abamectin is typically applied in weight ratios of 50:1 to 1:50. The remaining rows of Table D1 are structured similarly.

[0488] [Table 29]

[0489] [Table 30]

[0490] [Table 31]

[0491] Tables D2 to D15 are structured similarly to Table D1, except that the items under the heading of the "Component (a)" column are replaced with the respective "Component (a)" column items shown below. Therefore, for example, in Table D2, all items under the heading of the "Component (a)" column are "compounds". The document lists "Compound 18," and the first row below the heading in Table D2 specifically discloses a mixture of Compound 18 and abamectin. Tables D3 to D15 are structured similarly.

[0492] [Table 32]

[0493] A composition comprising a compound of Formula 1 useful for seed treatment may further contain bacteria and fungi having the ability to provide protection from harmful effects on soil-borne animals such as plant pathogenic fungi or bacteria and / or nematodes. Nematocidative bacteria may include, but are not limited to, Bacillus firmus, Bacillus cereus, Bacillis subtiliis, and Pasteuria penetrans. A suitable Bacillus firmus strain is CNCM I-1582 (GB-126), marketed as BioNem®. A suitable Bacillus cereus strain is NCMM I-1592. Both Bacillus strains are disclosed in U.S. Patent No. 6,406,690. Other suitable bacteria exhibiting nematicidal activity include B. amyloliquefaciens IN937a and Bacillus subtilis strain GB03. Bactericidal bacteria may include, but are not limited to, B. pumilus strain GB34. Nematical fungi may include, but are not limited to, Myrothecium verrucaria, Paecilomyces lilacinus, and Purpureocillium lilacinum.

[0494] Seed treatment may also include one or more naturally occurring nematicides, such as elicitor proteins called harpins isolated from certain bacterial plant pathogens, including the blight bacterium (Erwinia amylovora). An example is N-Hibit® Gold. One example is the Harpin-N-Tek seed treatment technology, which is available as a CST (Consumer Science Technology).

[0495] Seed treatments may also include one or more microsymbiotic nitrogen-fixing bacteria, such as soybean rhizobia (Bradyrhizobium japonicum), and other leguminous nodulating bacteria. These inoculants may optionally contain one or more lipochitooligosaccharides (LCOs), which are nodulation factors produced by rhizobia at the initiation of root nodulation in leguminous plants. For example, seed treatment technologies under the Optimize® brand incorporate LCO Promoter Technology® in combination with the inoculant.

[0496] Seed treatment is one or more methods that can increase the level of root establishment by mycorrhizal fungi. They may also contain isoflavones. Mycorrhizal fungi improve plant growth by enhancing the root uptake of nutrients such as water, sulfates, nitrates, phosphates, and metals. Examples of isoflavones include, but are not limited to, genistein, biochanin A, formononetin, daidzein, glycitein, hesperetin, naringenin, and platencein. Formononetin can be used as an active ingredient in mycorrhizal fungal inoculants such as PHC Colonize® AG.

[0497] Seed treatment may also include one or more plant activators that induce systemic acquired resistance in plants after contact with the pathogen. An example of a plant activator that induces such a protective mechanism is acibenzolar-S-methyl.

[0498] In this fungicidal composition, the formula 1 compound of component (a) acts synergistically with the additional fungicidal compound of component (b) to broaden the spectrum of plant diseases controlled, extend the duration of preventive and therapeutic protection, and suppress the growth of resistant fungal pathogens, providing beneficial results. In certain embodiments, compositions comprising a ratio of component (a) and component (b) that are particularly useful for controlling specific fungal diseases (such as Alternaria solani, Blumeria graminis f.sp. tritici, Botrytis cinerea, Puccinia recondita f.sp. tritici, Rhizoctonia solani, Septoria nodorum, and Septoria tritici) are provided according to the present invention.

[0499] Furthermore, mixtures of fungicides can provide significantly better disease control than would be predicted based on the activity of the individual components. This synergistic effect is described as "the cooperative action of two components of a mixture such that the combined effect is greater than or lasts longer than the sum of the two (or more) effects taken independently" (see PMLTames, Neth.J. Plant Pathology 1964, 70, 73-80). In a method of providing plant disease control through a synergistic effect from a combination of active ingredients (e.g., fungicide compounds) applied to plants or seeds, the active ingredients are applied in a synergistic weight ratio and a synergistic (i.e., synergistically effective) amount. The measure of disease control, suppression, and prevention cannot exceed 100%. Therefore, to achieve a substantial synergistic effect, it is typically necessary to use application rates of the active ingredients such that each individual ingredient provides a much less than 100% effect, and the additive effect should be substantially less than 100%, taking into account the potential increase in effect due to the synergy. On the other hand, if the application rate of the active ingredient is too low, it may not exhibit much activity in the mixture, even if there are synergistic benefits. Those skilled in the art can easily determine and optimize the weight ratio and application rate (i.e., amount) of the bactericidal compound that produces a synergistic effect through simple experiments.

[0500] The existence of a synergistic effect between the two active ingredients was established using the Colby equation (see Colby, SR, "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations," Weeds, (1967), 15, 20-22).

number

[0501] Using Colby's method, the existence of a synergistic interaction between two active ingredients is first established by calculating the predicted activity p of the mixture based on the activity of each ingredient when applied individually. If p is lower than the experimentally established effect, a synergistic effect has occurred. In the above equation, A is the % control fungicidal activity of one ingredient applied alone at rate x. Term B is the % control fungicidal activity of the second ingredient applied at rate y. The equation estimates p, the predicted fungicidal activity of the mixture of A at rate x and B at rate y, assuming that the effects are strictly additive and no interaction occurs.

[0502] Seed treatment may also include one or more plant activators that induce systemic acquired resistance in plants following contact with the pathogen. An example of a plant activator that induces such protective mechanisms is acibenzolar-S-methyl.

[0503] The following tests demonstrate the control efficacy of the compounds of the present invention against specific pathogens. However, the pathogen control protection provided by the compounds is not limited to these species. Please refer to Index Tables A and B below for a description of the compounds. The following abbreviations are used in Index Table A: Me means methyl, i-Pr means isopropyl, MeO means methoxy, and -NO2 means nitro. The abbreviation "Cmpd." is an abbreviation for "compound," and the abbreviation "Ex." is an abbreviation for "example," followed by a number indicating which example the compound is prepared in. In Index Table A, substituent R 4 and R 5 The locant numbers listed are as shown in the structure above the table. Substituent R 4 and R 5 The order in which the elements are listed may differ from the naming system of Chemical Abstracts, if the difference does not affect the meaning. For example, compound 1 in index table A is substituent R 5It is listed that is at position 6 (i.e., 6-F), while the CAS name for compound 1 is 4-(2-bromo-4,6-difluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine. + The values ​​reported in (M+1) represent the H to the molecule with the highest isotopic abundance (i.e., M). + The molecular weight of the observed molecular ion formed by the addition of (1 molecular weight) is shown in the column "AP". - The values ​​reported in (M-1) are from the molecule with the highest isotopic abundance (i.e., M) + This is the molecular weight of the observed molecular ion formed by the loss of (molecular weight 1). One or more isotopes of higher atomic weight with lower abundance (e.g., 37 Cl, 81 The presence of molecular ions containing Br) is not reported. The reported M+1 and M-1 peaks were observed by mass spectrometry using electrospray ionization (ESI) or atmospheric pressure chemical ionization (APCI).

[0504] [Table 33]

[0505] [Table 34]

[0506] [Table 35]

[0507] [Table 36]

[0508] [Table 37]

[0509] [Table 38]

[0510] [Table 39]

[0511] Biological embodiments of the present invention General protocol for preparing test suspensions for tests A-F: The test compound was first dissolved in acetone in an amount equal to 3% of the final volume, and then suspended at the desired concentration (in ppm) in a mixture of acetone and purified water (50 / 50 by volume) containing 250 ppm of the surfactant PEG400 (polyhydric alcohol ester). The resulting test suspensions were used for tests A-F.

[0512] Test A The test solution was sprayed onto wheat seedlings until it dripped onto them. The following day, the seedlings were inoculated with a spore suspension of Septoria tritici (the causative agent of wheat leaf blight), incubated in a saturated atmosphere at 24°C for 48 hours, and then transferred to a growth chamber at 20°C for 17 days. After this period, disease evaluation was performed.

[0513] Test B The test solution was sprayed onto the wheat seedlings until it was running down. The next day, Puscinia recondita was applied to the seedlings. A spore suspension of Puccinia recondita f.sp. tritici (the causative agent of wheat leaf rust) was inoculated and cultured for 24 hours in a saturated atmosphere at 20°C. The cultures were then transferred to a growth chamber at 20°C and cultured for 7 days, after which disease evaluation was performed.

[0514] Test C The test suspension was sprayed onto wheat seedlings until it dripped. The following day, the seedlings were inoculated with spore powder of Blumeria graminis f.sp. tritici (also known as Erysiphe graminis f.sp. tritici, the causative agent of wheat powdery mildew), incubated in a growth chamber at 20°C for 8 days, and then visually assessed for disease severity.

[0515] Test D The test solution was sprayed onto soybean seedlings until it dripped onto them. The following day, the seedlings were inoculated with a spore suspension of Phakopsora pachyrhizi (the causative agent of Asian soybean rust), incubated in a saturated atmosphere at 22°C for 24 hours, and then transferred to a growth chamber at 22°C for 8 days. After this period, a visual assessment of the disease was performed.

[0516] Test E The test suspension was sprayed onto tomato seedlings until it dripped. The following day, the seedlings were inoculated with a spore suspension of Botrytis cinerea (the causative agent of tomato botrytis disease), incubated in a saturated atmosphere at 20°C for 48 hours, and then transferred to a growth chamber at 24°C for 3 days. After this period, a visual assessment of the disease was performed.

[0517] Test F The test suspension was sprayed onto tomato seedlings until it dripped. The following day, the seedlings were inoculated with a spore suspension of Alternaria solani (the causative agent of summer blight in tomatoes), incubated in a saturated atmosphere at 27°C for 48 hours, and then transferred to a growth chamber at 20°C for 3 days. After this period, a visual assessment of the disease was performed.

[0518] The results for tests A through F are shown in Table A below. A rating of 100 indicates 100% disease control, and a rating of 0 indicates no disease control (compared to the control). A dash (-) indicates that the compound was not tested.

[0519] [Table 40]

[0520] [Table 41]

[0521] [Table 42]

[0522] [Table 43]

[0523] [Table 44]

[0524] [Table 45]

[0525] [Table 46]

[0526] The test results presented above in Table A for the compound of Formula 1 exemplify the fungicidal activity of component (a) that brings about the usefulness of a composition containing component (b) and component (a) optionally combined with at least one further fungicidal compound according to the present invention for controlling plant diseases.

[0527] Biological comparison example General protocol for preparing test suspensions for tests A1-F1: The test compound was first dissolved in acetone in an amount equal to 3% of the final volume, and then suspended at the desired concentration (ppm) in acetone and purified water (50 / 50 mix depending on the volume) containing 250 ppm of the surfactant PEG400 (polyhydric alcohol ester). The test suspension thus obtained was then used in tests A1-F1.

[0528] Exam A1 The test solution was sprayed onto wheat seedlings until it dripped onto them. The following day, the seedlings were inoculated with a spore suspension of Septoria tritici (the causative agent of wheat leaf blight), incubated in a saturated atmosphere at 24°C for 48 hours, and then transferred to a growth chamber at 20°C for 17 days. After this period, disease evaluation was performed.

[0529] Exam B1 The test solution was sprayed onto wheat seedlings until it dripped onto them. The following day, the seedlings were inoculated with a spore suspension of Puccinia recondita f.sp. tritici (the causative agent of wheat rust disease), incubated in a saturated atmosphere at 20°C for 24 hours, and then transferred to a growth chamber at 20°C for 7 days. After this period, disease evaluation was performed.

[0530] Exam C1 The test suspension was sprayed onto wheat seedlings until it dripped. The following day, the seedlings were exposed to spores of Blumeria graminis f.sp. tritici (also known as Erysiphe graminis f.sp. tritici, the causative agent of wheat powdery mildew). The powder was inoculated and incubated in a growth chamber at 20°C for 8 days. After this period, a visual disease assessment was performed.

[0531] Exam E1 The test suspension was sprayed onto tomato seedlings until it dripped. The following day, the seedlings were inoculated with a spore suspension of Botrytis cinerea (the causative agent of tomato botrytis disease), incubated in a saturated atmosphere at 20°C for 48 hours, and then transferred to a growth chamber at 24°C for 3 days. After this period, a visual assessment of the disease was performed.

[0532] Test F1 The test suspension was sprayed onto tomato seedlings until it dripped. The following day, the seedlings were inoculated with a spore suspension of Alternaria solani (the causative agent of summer blight in tomatoes), incubated in a saturated atmosphere at 27°C for 48 hours, and then transferred to a growth chamber at 20°C for 3 days. After this period, a visual assessment of the disease was performed.

[0533] The results for experiments A1 to F1 are shown in Table B below. A rating of 100 indicates 100% disease control, and a rating of 0 indicates no disease control (compared to the control). Data is presented for the following compounds. [ka]

[0534] [Table 47]

Claims

1. A bactericidal composition, (a) Formula 1: 【Chemistry 1】 (In the formula, R １ C １ ~C ２ It is alkyl, R ２ These are cyano, halogen, and C １ ~C ２ Alkyl or C １ ~C ２ It is a haloalkyl, R ３ is halogen or methyl, Each R ４ These are, independently, halogen, cyano, nitro, and C １ ~C ３ Alkyl, C １ ~C ３ Alkoxy, C １ ~C ３ Haloalkoxy, C ２ ~C ６ Alkenyloxy, C ２ ~C ６ Alkynyloxy, C ２ ~C ６ Cyanoalkoxy, C ２ ~C ６ Alkoxyalkyl or C ２ ~C ６ It is an alkoxyalkoxy, Each R ５ These are, independently, halogen, C １ ~C ３ Alkyl, C ２ ~C ６ Alkoxyalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ Haloalkoxy, C ２ ~C ６ Alkenyloxy, C ２ ~C ６ Alkynyloxy, C ２ ~C ６ Cyanoalkoxy or C ２ ~C ６ It is an alkoxyalkoxy, m and n are independently 0, 1, 2, or 3. R ６ is H; or R ６ａ C is optionally substituted with up to two substituents that are independently selected from the original C １ ~C ３ Alkyl or C １ ~C ３ Haloalkyl; or amino, C ２ ~C ４ Alkenil, C ２ ~C ４ Alkinyl, C ３ ~C ６ Cycloalkyl, CH(=O), S(=O) ２ OM, S (=O) ｕ R ７ (C=W)R ８ OR ９ And, Each R ６ａ These are independently cyano, C ３ ~C ６ Cycloalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ Haloalkoxy, C １ ~C ３ Alkylthio, C １ ~C ３ Alkyl sulfinyl or C １ ~C ３ It is an alkylsulfonyl, M is either K or Na. u is 0, 1, or 2. R ７ C １ ~C ３ Alkyl or C １ ~C ３ It is a haloalkyl, W is either O or S, R ８ is C １ to C ３ alkyl, C ２ to C ４ alkoxyalkyl, C ２ to C ４ alkylaminoalkyl, C ３ to C ６ dialkylaminoalkyl, C １ to C ３ alkoxy, C １ to C ３ alkylthio or C ２ to C ４ alkylthioalkyl, and R ９ is optionally substituted with up to two substituents independently selected from H; or R ９ａ C optionally substituted with up to two substituents independently selected from １ to C ３ alkyl or C １ to C ３ haloalkyl; or CH(=O), C ３ to C ６ cycloalkyl, S(=O) ２ OM or (C=W)R １０ wherein Each R ９ａ These are independently cyano, C ３ ~C ６ Cycloalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ Haloalkoxy, C １ ~C ３ Alkylthio, C １ ~C ３ Alkyl sulfinyl or C １ ~C ３ It is an alkylsulfonyl, and R １０ C １ ~C ３ Alkyl, C ２ ~C ４ Alkoxyalkyl, C ２ ~C ４ Alkyl Minoalkyl, C ３ ~C ６ Dialkylaminoalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ Alkylthio or C ２ ~C ４ (It is alkylthioalkyl) A compound selected from the compound, its N-oxide and salt, (b) at least one additional bactericidal compound and This includes, however, the compound of formula 1 is 4-(2,6-difluoro-4-methoxyphenyl)-N-(2,4-difluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-N-(2-nitrophenyl)-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2,4-difluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-3-ethyl-1-methyl-N-(2-nitrophenyl)-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-1-methyl-N-(2-nitrophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-amine, 4-(2,6-difluoro-4-methoxyphenyl)-N-(2-methoxy-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-methoxy-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, N-(2-chloro-6-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazole-5-amine, N-(2-chloro-3-fluoro-6-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-N-(2-methyl-6-nitrophenyl)-1H-pyrazole-5-amine, N-(2-bromo-4-fluoro-6-nitrophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(4-methoxy-2-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2,6-difluoro-4-methoxyphenyl)-N-(4-fluoro-2-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2,6-difluoro-4-methoxyphenyl)-N-(4-methoxy-2-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, N-(4-chloro-2-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-N-[2-nitro-4-(2-propyne-1-yloxy)phenyl]-1H-pyrazole-5-amine, 4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-N-[2-nitro-4-(2-propene-1-yloxy)phenyl]-1H-pyrazole-5-amine, N-(4-bromo-2-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazole-5-amine, N-(4-chloro-2-fluoro-6-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 3-Chloro-4-(2-chloro-4-fluorophenyl)-N-(2,4-difluoro-6-nitrophenyl)-1-methyl-1H-pyrazole-5-amine, 4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-N-[4-methyl-2-nitrophenyl]-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-N-(4-methyl-2) -nitrophenyl)-1H-pyrazole-5-amine, and N-(4-bromo-2-fluoro-6-nitrophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazole-5-amine A bactericidal composition, provided that it is not [the specified condition].

2. Component (a) comprises the compound of formula 1 or a salt thereof, R １ It is methyl, R ２ is cyano, halogen or C １ ~C ２ It is alkyl, R ３ It is a halogen, Each R ４ These are independently halogen, cyano, methyl, methoxy, halomethoxy, and C ２ ~C ４ Alkenyloxy, C ２ ~C ４ Alkinyloxy or C ２ ~C ４ It is a cyanoalkoxy, Each R ５ These are, independently, halogen, methyl, methoxy, halomethoxy, and C. ２ ~C ４ Alkenyloxy, C ２ ~C ４ Alkinyloxy or C ２ ~C ４ It is a cyanoalkoxy, R ６ is H; or R ６ａ Each C is optionally substituted with up to one substituent selected from the following. １ ~C ２ Alkyl or C １ ~C ２ Haloalkyl; or S (=O) ｕ R ７ OR ９ And, R ６ａ is cyano, C ３ ~C ６ Cycloalkyl or C １ ~C ３ It is an alkoxy, R ７ It is methyl or halomethyl, R ９ is H; or R ９ａ Each C is optionally substituted with up to one substituent selected from the following. １ ~C ２ Alkyl or C １ ~C ２ It is a haloalkyl, and R ９ａ is cyano, C ３ ~C ６ Cycloalkyl or C １ ~C ３ The composition according to claim 1, wherein it is an alkoxy.

3. Component (a) comprises the compound of formula 1 or a salt thereof, R ２ It is methyl or ethyl, R ３ is Br, Cl, or F, Each R ４ These are independently halogen, cyano, methyl, or methoxy. m is 1, and R ４ is in the para position, or m is 1, and R ４ is in the ortho position, or m is 2 and one R ４ One is in the para position, and the other is in the ortho position. Each R ５ These are independently halogen, methyl, or methoxy. n is 1, and R ５ is in the para position, or n is 1, and R ５ is in the ortho position, or n is 2 and one R ５ One is in the para position, and the other is in the ortho position, and R ６ The composition according to claim 2, wherein is H or methyl.

4. Component (a) comprises the compound of formula 1 or a salt thereof, R ２ It is methyl, Each R ４ These are independently Br, Cl, F, cyano, or methoxy. Each R ５ These are independently Br, Cl, F, methyl or methoxy, and R ６ The composition according to claim 3, wherein H is present.

5. Component (a) comprises the compound of formula 1 or a salt thereof, Each R ４ These are independently Br, Cl or F, and m and n are each 1, and R ４ It is in the para position, and R ５ is in the ortho position, or m is 1, and R ４ It is in the para position, and n is 2, and one R ５ One is in the para position and the other is in the ortho position, or m is 2 and one R ４ One is in the para position and the other is in the ortho position, and n is 1, and R ５ The composition according to claim 4, wherein the ortho position is located.

6. Component (a) comprises the compound of formula 1 or a salt thereof, R ４ is either Cl or F, Each R ５ These are independently Cl, F or methyl, and m and n are each 1, and R ４ It is in the para position, and R ５ is in the ortho position, or m is 1, and R ４ It is in the para position, and n is 2, and one R ５ The composition according to claim 5, wherein one atom is in the para position and the other is in the ortho position.

7. Component (a) comprises the compound of formula 1 or a salt thereof, R １ It is methyl, R ２ It is methyl or ethyl, R ３ It is a halogen, Each R ４ These are independently Br, Cl, F, cyano, or methoxy. m is 1, and R ４ is in the para position, or m is 1, and R ４ is in the ortho position, or m is 2 and one R ４ One is in the para position, and the other is in the ortho position. n is 0, and R ６ The composition according to claim 1, wherein is H or methyl.

8. Component (a) comprises the compound of formula 1 or a salt thereof, R ２ It is methyl, R ３ is Br, Cl, or F, Each R ４ These are independently Br, Cl, or F. m is 1, and R ４ is in the para position, or m is 1, and R ４ is in the ortho position, or m is 2 and one R ４ One is in the para position, and the other is in the ortho position, and R ６ The composition according to claim 7, wherein is H.

9. Component (a) is, 4-(2-bromo-4,6-difluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 3-Chloro-4-[5-[(2-Chloro-4-fluoro-6-nitrophenyl)amino]-1,3-dimethyl-1H-pyrazole-4-yl]benzonitrile, N-(2-chloro-4-fluoro-6-nitrophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-6-fluorophenyl)-N-(2-fluoro-4-methoxy-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2,4-difluorophenyl)-N-(2-fluoro-4-methoxy-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4,6-difluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-3-ethyl-1-methyl-1H-pyrazole-5-amine, N-(2-chloro-4-fluoro-6-nitrophenyl)-4-(2-chloro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-4-methyl-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(4-fluoro-2-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2,4-difluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, N-(4-chloro-2-fluoro-6-nitrophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, and 3-Chloro-4-[5-[(2-fluoro-4-methyl-6-nitrophenyl)amino]-1,3-dimethyl-1H-pyrazole-4-yl]benzonitrile The composition according to claim 1, comprising a compound selected from the group consisting of the following.

10. Component (a) is, 4-(2-bromo-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4,6-difluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-3-ethyl-1-methyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-4-methyl-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, and 4-(2,4-difluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazole-5-amine The composition according to claim 8, comprising a compound selected from the group consisting of the following.

11. Component (b) is, (b1) Methylbenzimidazole carbamate (MBC) fungicide, (b2) Dicarboxyimide fungicide, (b3) Demethylation inhibitor (DMI) bactericides, (b4) Phenylamide (PA) bactericides, (b5) Amine / morpholine fungicides, (b6) Phospholipid biosynthesis inhibitors, bactericides, (b7) Succinate dehydrogenase inhibitor (SDHI) bactericides, (b8) Hydroxy(2-amino-)pyrimidine fungicide, (b9) Anilinopyrimidine (AP) fungicide, (b10) N-phenylcarbamate fungicide, (b11) Quinone outside inhibitor (QoI) bactericides, (b12) Phenylpyrrole (PP) fungicide, (b13) Azanaphthalene fungicide, (b14) Cell peroxidation inhibitor bactericides, (b15) Melanin biosynthesis inhibitor-reductase (MBI-R) bactericide, (b16a) Melanin biosynthesis inhibitor - dehydratase (MBI-D) bactericide, (b16b) Melanin biosynthesis inhibitor - polyketide synthase (MBI-P) bactericide, (b17) Ketoreductase inhibitor (KRI) bactericides, (b18) Squalene-epoxidase inhibitor bactericide, (b19) Polyoxin disinfectant, (b20) Phenylurea fungicide, (b21) Quinone inside inhibitor (QiI) bactericide, (b22) Benzamide and thiazole carboxamide fungicides, (b23) Enopyranuronic acid antibiotic bactericide, (b24) Hexopyranosyl antibiotic fungicide, (b25) Glucopyranosyl antibiotics: protein synthesis bactericides, (b26) Glucopyranosyl antibiotic fungicide, (b27) Cyanoacetamido oxime fungicide, (b28) Carbamate fungicides, (b29) Oxidative phosphorylation uncoupling fungicides, (b30) Organotin fungicides, (b31) Carboxylic acid fungicide, (b32) Heterocyclic aromatic compound fungicides, (b33) Phosphonate fungicides, (b34) Phthalamitic acid fungicide, (b35) Benzotriazine fungicide, (b36) Benzene sulfonamide fungicide, (b37) Pyridazinone fungicide, (b38) Thiophen-carboxamide fungicide, (b39) Complex I NADH oxidoreductase inhibitor bactericide, (b40) Carboxylic acid amide (CAA) bactericides, (b41) Tetracycline antibiotics and fungicides, (b42) Thiocarbamate fungicides, (b43) Benzamide fungicide, (b44) Microbial disinfectants, (b45) Quinone outside inhibitors, stigmatelin-conjugated (QoSI) bactericides, (b46) Plant extract fungicide, (b47) Cyanoacrylate fungicides, (b48) Polyene fungicides, (b49) Oxysterol-binding protein inhibitors (OSBPIs) bactericides, (b50) Aryl-phenyl-ketone fungicide, (b51) Host plant defense-inducing fungicides, (b52) Multi-site active fungicide, (b53) Biological agents having multiple mechanisms of action, (b54) Bactericides other than those of component (a) and components (b1) to (b53), and salts of compounds (b1) to (b54) The composition according to any one of claims 1 to 7, comprising at least one bactericidal compound selected from the group consisting of the following.

12. The composition according to claim 11, wherein component (b) comprises at least one bactericidal compound from each of two different groups selected from (b1) to (b54).

13. Ingredient (b) is acibenzolar-S-methyl, algimorph, ametocrazine, amisulbrom, anilazine, azaconazole, azoxystrobin, venalaxyl, venalaxyl-M, benodanil, benomyl, bentheavalicarb, bentheavalicarb-isopropyl, benzovindiflupir, betoxazine, binapacril, biphenyl, vitertanol, bixafen, blastosidine-S, boscalid, bromconazole, bupirime Carboxyne, carpropamide, captahol, captan, carbendazim, chloroneb, chlorothalonil, clozolinate, clotrimazole, copper hydroxide, copper salt, cyazofamide, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, diclofluanid, diclocimeth, diclomedin, dichloran, diethofencarb, difenoconazole, diflumetrim, dimethyrimol, dimethomorph, dimoxystrobin, din Conazole, diniconazole-M, dinocap, dithianone, dodemorph, dozin, edifenfos, enestrobrin, epoxyconazole, etaboxam, etirimol, etridiazole, famoxadone, phenamidon, phenarimol, fenbuconazole, fenflam, fenhexamide, phenoxanil, fenpiclonil, fenpropidine, fenpropimorph, fenpyrazamine, fentin acetate, fentin chloride, fentin hydroxide, ferubam, ferimzon, fluazinam, fludioxonil, fluindapir, flumetbel, Flumorph, fluopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, fluthianil, flutolanil, flutriafole, fluxapyroxad, flupet, fosetyl-aluminum, fuberidazole, fluraxyl, flametopyr, hexaconazole, himexazole, guazatine, imazalil, imibenconazole, iminoctadine, iodocarb, ipconazole, ipfentrifluconazole, iprobenphos, iprodione, iprovalicarb, isoprothiolane, i Sopirazam, Isothianil, Kasugamycin, Kresoxim-methyl, Mancozeb, Mandipropamide, Maneb, Mepronil, Meptyldinocap, Metalaxyl, Metalaxyl-M, Metconazole, Metasulfocarb, Methylam, Metminostrobin, Mepanipyrim, Metraphenone, Mycrobutanil, Naphthifine, Neo-Asodine (ferrous methanearsone), Nualimol, Octylinone, Oflace, Orysastrobin, Oxadixyl, Oxolinic acid, Oxypoconazole, Oxycarboxyne, Oxytetracycline, Penconazole, Pensic Ron, Penflufen, Penthiopyrad, Peflazoate, Phosphate and its salts, Phthalide, Picoxystrobin, Piperalin, Polyoxin, Probenazole, Prochloraz, Procymidone, Propamocarb, Propamocarb-hydrochloride, Propiconazole, Propineb, Proquinazide, Prothiocarb, Prothioconazole, Pidiflumetofen, Pyraclostrobin, Pyramethostrobin, Pyraoxystrobin, Pyrazofos, Piribencarb, Pyributicarb, Pyriphenox, Pyrimethanil, Pyriophenone, Pyrisoxazole, Pyrokylone,Pyrrolnitrin, quinomethionate, quinoxyfen, quintozen, sedaxane, silthiofam, simeconazole, spiroxamine, streptomycin, sulfur, tebuconazole, tebufloxin, tecrophthalam, technazen, terbinafine, tetraconazole, thiabendazole, tifluzamide, thiophanate, thiophanate-methyl, thyram, thiadinyl, tolclophos-methyl, tolfluanide, tornifanide, triadimefone, triadimenol, triazoxide, tricyclazole, tridemorph, triflumizole, tricyclazole L, trifloxystrobin, triforine, trimorphamide, triticonazole, uniconazole, validamycin, valifenarate, vinclozoline, zineb, dilam, zoxamide, N'-[4-[4-chloro-3-(trifluoromethyl)phenoxy]-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidoamide, 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidine-1-yl)[1,2,4]triazolo[1,5a]pyrimidine (DPX-BAS600F), N-[2-[4-[[3-( 4-chlorophenyl)-2-propyne-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulfonyl)amino]butanamide, N-[2-[4-[[3-(4-chlorophenyl)-2-propyne-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(ethylsulfonyl)amino]butanamide, 4-fluorophenyl N-[1-[[[1-(4-cyanophenyl)ethyl]sulfonyl]methyl]propyl]carbamate, N-[[(cyclopropylmethoxy)amino][6-(difluoromethyl Xy)-2,3-difluorophenyl]methylene]benzeneacetamide, α-(methoxyimino)-N-methyl-2-[[[1-[3-(trifluoromethyl)phenyl]ethoxy]imino]methyl]benzeneacetamide, N'-[4-[4-chloro-3-(trifluoromethyl)phenoxy]-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidoamide, 2-[[[[3-(2,6-dichlorophenyl)-1-methyl-2-propene-1-ylidene]amino]oxy]methyl]-α-(methoxyimino)-N-methylbenzeneacetamide, The composition according to any one of claims 1 to 7, comprising toamide and at least one compound selected from 1-[(2-propenylthio)carbonyl]-2-(1-methylethyl)-4-(2-methylphenyl)-5-amino-1H-pyrazole-3-one, 5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidine-7-ylamine.

14. The composition according to claim 13, wherein component (b) comprises at least one compound selected from azoxystrobin, benzovindiflupyr, bixafen, chlorothalonil, copper hydroxide, cyproconazole, epoxyconazole, fenpropidine, fenpropimorph, fluindapyr, flutriafole, fluxapiroxad, mancozeb, metminostrobin, picoxystrobin, prothioconazole, pidflumetofen, pyraclostrobin, tebuconazole, and trifloxystrobin.

15. A composition comprising the composition according to claim 1 and at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents.

16. A method for protecting plants or plant seeds from diseases caused by fungal pathogens, comprising applying a bactericidal effective amount of the composition according to any one of claims 1 to 14 to the plants or plant seeds.

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