Composition and method for controlling plant diseases by plasmodiophores

Abstract

A composition for controlling plant diseases by plasmodiophores, the composition comprising a compound represented by formula (1) or a salt thereof as an active ingredient, wherein, in the formula , Ar1 represents a phenyl group that is unsubstituted or substituted with n R1s, each of the R1s represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, or a cyano group, n represents an integer of 1-5, Ar2 represents a phenyl group that is unsubstituted or substituted with 1-5 R2s, each of the R2s represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, or a cyano group, m represents an integer of 1-5, X represents -NH- or a direct bond, and Q represents a group having a nitrogen-containing ring structure (a 2-pyridone backbone, a pyridazine backbone, or a pyrazole backbone).

Description

Composition and method for controlling plant diseases caused by rhododendrons

[0001] The present invention relates to a composition and a method for controlling plant diseases caused by Porphyromonas spp. This application claims priority to Japanese Patent Application No. 2024-107719, filed on July 3, 2024, the contents of which are incorporated herein by reference.

[0002] Plasmodiophora is a fungus belonging to the kingdom Protozoa, phylum Cercozoa, class Phytomyxida, order Plasmodiophorales, and family Plasmodiophoridae. A major plant disease caused by Plasmodiophora is known as clubroot disease of cruciferous crops, which is caused by the pathogen Plasmodiophora brassicae. This disease is a soil-borne plant disease that infects the roots of cruciferous crops and shows club-like symptoms. The roots of plants infected with this disease have a reduced ability to absorb nutrients and water, and if the disease becomes severe, they will wither and die.

[0003] Other known plant diseases caused by the root fungi include, for example, potato powdery scab caused by Spongospora subterranea, and sugar beet root disease caused by a pathogenic virus transmitted by Polymyxa betae. The potato powdery scab fungus is known to infect Solanaceae plants such as potato, tomato, and eggplant.

[0004] Conventionally, chemical pesticides have been mainly used to control plant diseases caused by Plasmodiophora. For example, Patent Document 1 discloses flusulfamide and fluazinam as fungicides capable of controlling clubroot disease.

[0005] Japanese Unexamined Patent Publication No. 8-000071

[0006] However, there are few options for chemicals that have a control effect against the above-mentioned plant diseases. In addition, when the disease level of the target plant is severe or when the pathogenicity of the target fungus is strong, the control effect of conventional chemicals may be insufficient. Therefore, there is a demand for the development of a new control composition that has an excellent control effect.

[0007] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a composition for controlling plant diseases caused by Porphyromonas spp., which has excellent control effect, and a control method using the control composition.

[0008] As a result of intensive research to solve the above problems, the present inventors have found that a compound represented by the following formula (1) or a salt thereof has an excellent control effect against plant diseases caused by Porphyromonas spp., and have completed the present invention.

[0009] That is, the present invention includes the following aspects: [1] A composition for controlling plant diseases caused by Porphyromonas spp., comprising a compound represented by formula (1) or a salt thereof.

[0010] [In the formula, Ar1 represents a phenyl group that is unsubstituted or substituted with n R1 groups. R1 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, or a cyano group. n represents an integer of 1 to 5. However, when n is an integer of 2 or greater, multiple R1 groups may be the same or different. Ar2 represents a phenyl group that is unsubstituted or substituted with m R2 groups. R2 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, or a cyano group. m represents an integer of 1 to 5. However, when m is an integer of 2 or greater, multiple R2 groups may be the same or different. X represents -NH- or a direct bond. Q represents a group having a nitrogen-containing ring structure represented by any of the following formulae (Q1) to (Q3).]

[0011] [In the formula, A represents Ar1 in the formula (1). B represents X-Ar2 in the formula (1). R3 represents a hydrogen atom, a chlorine atom, a methyl group, an ethyl group, or a normal propyl group. R4 represents a methyl group, an ethyl group, or a difluoroethyl group.]

[0012] [In the formula, A represents Ar1 in the formula (1). B represents X-Ar2 in the formula (1). R5 represents a hydrogen atom, a chlorine atom, a methyl group, an ethyl group, or a normal propyl group. R6 represents a chlorine atom, a methyl group, an ethyl group, or a difluoroethyl group.]

[0013] [In the formula, A represents Ar1 in the formula (1). B represents X-Ar2 in the formula (1). R7 represents a hydrogen atom, a chlorine atom, a methyl group, an ethyl group, or a normal propyl group. R8 represents a methyl group, an ethyl group, or a difluoroethyl group.]

[0014] [2] The composition for controlling plant diseases caused by Porphyromonas spp. according to [1], wherein the compound represented by formula (1) is a compound represented by the following formula (1-1):

[0015] [In the formula, Ar1 represents a phenyl group that is unsubstituted or substituted with n R1 groups. R1 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, or a cyano group. n represents an integer of 1 to 5. However, when n is an integer of 2 or greater, multiple R1 groups may be the same or different. Ar2 represents a phenyl group that is unsubstituted or substituted with m R2 groups. R2 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, or a cyano group. m represents an integer of 1 to 5. However, when m is an integer of 2 or greater, multiple R2 groups may be the same or different. R3 represents a hydrogen atom, a chlorine atom, a methyl group, an ethyl group, or a normal propyl group. R4 represents a methyl group, an ethyl group, or a difluoroethyl group.]

[0016] [3] The composition for controlling plant diseases caused by Porphyromonas spp. according to [1], wherein the compound represented by formula (1) is a compound represented by the following formula (1-2):

[0017] [Wherein, Ar1 represents an unsubstituted phenyl group. Ar2 represents a phenyl group substituted with two fluorine atoms.] [4] The composition for controlling plant diseases caused by Porphyromonas spp. according to [3], containing a compound represented by the following formula (2) or a salt thereof:

[0018]

[0019] [5] The composition for controlling plant diseases caused by Porphyromonas spp. according to [1], wherein the compound represented by formula (1) is a compound represented by the following formula (1-3):

[0020] [In the formula, Ar1 represents a phenyl group substituted with two R1. R1 represents a fluorine atom or a bromine atom. The two R1 may be the same or different. Ar2 represents a phenyl group substituted with two R2. R2 represents a fluorine atom or a chlorine atom. The two R2 may be the same or different.]

[0021] [6] The composition for controlling plant diseases caused by Porphyromonas spp. according to [5], which contains a compound represented by the following formula (3) or a salt thereof:

[0022]

[0023] [7] The composition for controlling plant diseases caused by P. cerevisiae according to any one of [1] to [6], wherein the plant diseases caused by P. cerevisiae are clubroot of cruciferous crops, powdery scab of potato, wheat yellow mosaic disease, barley yellow mosaic disease, and wheat-borne disease. [8] A method for controlling plant diseases caused by P. cerevisiae, comprising applying the composition according to [1] to [7] to plants, plant seeds, or soil for growing plants.

[0024] According to the present invention, it is possible to provide a composition for controlling plant diseases caused by Porphyromonas spp., which has excellent control effect, and a control method using said control composition.

[0025] Hereinafter, a mode for carrying out the present invention (hereinafter referred to as "the present embodiment") will be described in detail. The following present embodiment is an example for explaining the present invention, and is not intended to limit the present invention to the following content. The present invention can be modified in various ways without departing from the gist of the present invention. Note that, unless otherwise specified, each term used in the claims and specification shall be defined according to the definition commonly used in the relevant technical field.

[0026] <Composition for controlling plant diseases caused by Porphyromonas spp.> <Compound represented by formula (1) or salt thereof> The composition for controlling plant diseases caused by Porphyromonas spp. of the present embodiment (hereinafter, sometimes simply referred to as "the composition of the present embodiment") contains a compound represented by the following formula (1) or a salt thereof:

[0027] [In the formula, Ar1 represents a phenyl group that is unsubstituted or substituted with n R1 groups. R1 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, or a cyano group. n represents an integer of 1 to 5. However, when n is an integer of 2 or greater, multiple R1 groups may be the same or different. Ar2 represents a phenyl group that is unsubstituted or substituted with m R2 groups. R2 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, or a cyano group. m represents an integer of 1 to 5. However, when m is an integer of 2 or greater, multiple R2 groups may be the same or different. X represents -NH- or a direct bond. Q represents a group having a nitrogen-containing ring structure represented by any of the following formulae (Q1) to (Q3).]

[0028] [In the formula, A represents Ar1 in the formula (1). B represents X-Ar2 in the formula (1). R3 represents a hydrogen atom, a chlorine atom, a methyl group, an ethyl group, or a normal propyl group. R4 represents a methyl group, an ethyl group, or a difluoroethyl group.]

[0029] [In the formula, A represents Ar1 in the formula (1). B represents X-Ar2 in the formula (1). R5 represents a hydrogen atom, a chlorine atom, a methyl group, an ethyl group, or a normal propyl group. R6 represents a chlorine atom, a methyl group, an ethyl group, or a difluoroethyl group.]

[0030] [In the formula, A represents Ar1 in the formula (1). B represents X-Ar2 in the formula (1). R7 represents a hydrogen atom, a chlorine atom, a methyl group, an ethyl group, or a normal propyl group. R8 represents a methyl group, an ethyl group, or a difluoroethyl group.]

[0031] The compound represented by the formula (1) or a salt thereof is a nitrogen-containing heterocyclic compound in which two adjacent carbon atoms each independently have a substituent (Ar1, Ar2) containing a phenyl group. The compound represented by the formula (1) or a salt thereof has the same effect as the compound represented by the formula (1) or a salt thereof because it has the same structure as the compound represented by the formula (1), and has an excellent control effect against plant diseases caused by Porphyromonas spp., as shown in the examples described later.

[0032] [When Q in the above formula (1) is a group having a nitrogen-containing ring structure (2-pyridone skeleton) represented by the above formula (Q1)] X in the above formula (1) is preferably a direct bond.

[0033] More preferably, the compound represented by the above formula (1) is a compound represented by the following formula (1-1):

[0034] [In the formula, Ar1 represents a phenyl group that is unsubstituted or substituted with n R1 groups. R1 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, or a cyano group. n represents an integer of 1 to 5. However, when n is an integer of 2 or greater, multiple R1 groups may be the same or different. Ar2 represents a phenyl group that is unsubstituted or substituted with m R2 groups. R2 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, or a cyano group. m represents an integer of 1 to 5. However, when m is an integer of 2 or greater, multiple R2 groups may be the same or different. R3 represents a hydrogen atom, a chlorine atom, a methyl group, an ethyl group, or a normal propyl group. R4 represents a methyl group, an ethyl group, or a difluoroethyl group.]

[0035] When Ar1 is a substituted phenyl group, n may be an integer of 1 to 3, and may be 2 or 3.

[0036] When Ar1 is a monosubstituted phenyl group (n=1), R1 may be a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a trifluoromethyl group, or a methoxy group.

[0037] When Ar1 is a monosubstituted phenyl group (n=1), the substitution position of R1 in Ar1 may be the 2-position (ortho-position), the 3-position (meta-position), or the 4-position (para-position). The 2-position (ortho-position) may be substituted with a chlorine atom.

[0038] When Ar1 is a disubstituted phenyl group (n=2), the two R1 may be the same or different. One R1 may be a fluorine atom, a chlorine atom, or a methyl group, and the other may be a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, or an ethoxy group. Alternatively, one R1 may be a fluorine atom or a chlorine atom, and the other may be a fluorine atom or a methoxy group.

[0039] When Ar1 is a disubstituted phenyl group (n=2), the substitution positions of R1 on Ar1 may be the 2,3 positions (ortho, meta positions), the 2,4 positions (ortho, para positions), the 2,5 positions (ortho, meta positions), the 2,6 positions (ortho positions), or the 3,5 positions (meta positions).

[0040] Among these, the 2-position (ortho-position) may be substituted with a fluorine atom or a chlorine atom, or may be substituted with a chlorine atom. The 3-position (meta-position) may be substituted with a fluorine atom or a methoxy group. The 4-position (para-position) may be substituted with a fluorine atom, a bromine atom, a methyl group, or a methoxy group. The 5-position (meta-position) may be substituted with a fluorine atom, a chlorine atom, a methoxy group, or an ethoxy group, or may be substituted with a fluorine atom or a methoxy group. The 6-position (ortho-position) may be substituted with a fluorine atom.

[0041] When Ar1 is a trisubstituted phenyl group (n=3), the three R1 may be the same or different, and the three R1 may be at least one selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, and a methoxy group.

[0042] When Ar1 is a trisubstituted phenyl group (n=3), the substitution positions of R1 in Ar1 may be the 2-, 3-, and 5-positions (ortho, meta, and meta positions). In particular, the 2-position (ortho position) may be substituted with a chlorine atom, the 3-position (meta position) with a fluorine atom, and the 5-position (meta position) with a fluorine atom.

[0043] When Ar1 is a pentasubstituted phenyl group (n=5), the five R1 may be the same or different. When the five R1 are the same, each R1 may be a fluorine atom.

[0044] Ar2 in the above formula (1) may be an unsubstituted phenyl group, or may be a phenyl group substituted with m R2 (substituted phenyl group). When Ar2 is a substituted phenyl group, R2 may contain a methyl group, a methoxy group, or a halogen atom (fluorine atom, chlorine atom, bromine atom).

[0045] When Ar2 is a substituted phenyl group, m may be an integer of 1 to 3, and may be 2 or 3.

[0046] When Ar2 is a monosubstituted phenyl group (m=1), R2 may be a fluorine atom, a bromine atom, a methyl group, a methoxy group, or a cyano group, or may be a methoxy group or a cyano group.

[0047] When Ar2 is a monosubstituted phenyl group (m=1), the substitution position of R2 on Ar2 may be the 4-position (para-position).

[0048] When Ar2 is a disubstituted phenyl group (m=2), the two R2 may be the same or different. When the two R2 are the same, each R2 may be a fluorine atom.

[0049] When Ar2 is a disubstituted phenyl group (m=2), the substitution positions of R2 in Ar2 may be the 2- and 6-positions (ortho positions).

[0050] When Ar2 is a trisubstituted phenyl group (m=3), the three R2 may be the same or different. The three R2 may be at least one selected from the group consisting of a fluorine atom, a chlorine atom, a methyl group, and a methoxy group. When the three R2 are the same, each R2 may be a fluorine atom.

[0051] When Ar2 is a trisubstituted phenyl group (m=3), the substitution positions of R2 in Ar2 may be the 2-, 4-, and 6-positions (ortho-, para-, and ortho-positions). Among these, the 2-position (ortho-position) may be a fluorine atom, the 4-position (para-position) may be a fluorine atom, a chlorine atom, a methyl group, or a methoxy group, and the 6-position (ortho-position) may be a fluorine atom, or each of these may be a fluorine atom.

[0052] R3 in the above formula (Q1) may be a hydrogen atom, a chlorine atom, or a methyl group, or may be a hydrogen atom, a chlorine atom, or a methyl group.

[0053] R4 in the above formula (Q1) may be a methyl group, an ethyl group, or a difluoroethyl group.

[0054] [When Q in the above formula (1) is a group having a nitrogen-containing ring structure (pyridazine skeleton) represented by the above formula (Q2)] Preferably, the compound represented by the above formula (1) is a compound represented by the following formula (1-2):

[0055] [In the formula, Ar1 represents an unsubstituted phenyl group, and Ar2 represents a phenyl group substituted with two fluorine atoms.]

[0056] The substitution positions of R2 (fluorine atom) in Ar2 are preferably the 2- and 6-positions (ortho-positions).

[0057] That is, the compound represented by the above formula (1) is preferably a compound (pyridachloromethyl) represented by the following formula (2):

[0058]

[0059] [When Q in the above formula (1) is a group having a nitrogen-containing ring structure (pyrazole skeleton) represented by the above formula (Q3)] Ar1 in the above formula (1) is preferably a phenyl group substituted with n R1. Among them, R1 is preferably a fluorine atom or a bromine atom. When n is an integer of 2 or more, multiple R1 may be the same or different. n is preferably 2. When n is 2, it is preferable that one of R1 is a fluorine atom and the other is a bromine atom. Furthermore, when n is 2, the substitution positions of R1 in Ar1 are preferably the 2- and 4-positions (ortho and para positions).

[0060] Ar2 in the above formula (1) is preferably a phenyl group substituted with m R2. Among these, R2 is preferably a fluorine atom or a chlorine atom. When m is an integer of 2 or more, the multiple R2 may be the same or different. m is preferably 2. When m is 2, it is preferable that one of R2 is a fluorine atom and the other is a chlorine atom. Furthermore, when m is 2, the substitution positions of R2 in Ar2 are preferably the 2- and 6-positions (ortho positions).

[0061] X in the above formula (1) is preferably —NH—.

[0062] R7 in the above formula (Q3) is preferably a methyl group.R8 in the above formula (Q3) is preferably a methyl group.

[0063] More preferably, the compound represented by the above formula (1) is a compound represented by the following formula (1-3):

[0064] [In the formula, Ar1 represents a phenyl group substituted with two R1. R1 represents a fluorine atom or a bromine atom. The two R1 may be the same or different. Ar2 represents a phenyl group substituted with two R2. R2 represents a fluorine atom or a chlorine atom. The two R2 may be the same or different.]

[0065] Of the two R1 in Ar1, it is preferable that one is a fluorine atom and the other is a bromine atom. Furthermore, the substitution positions of R1 in Ar1 are preferably the 2- and 4-positions (ortho and para positions). Of the two R2 in Ar2, it is preferable that one is a fluorine atom and the other is a chlorine atom. Furthermore, it is preferable that the substitution positions of R2 in Ar2 are the 2- and 6-positions (ortho positions).

[0066] More preferred is a compound represented by the following formula (3):

[0067]

[0068] The compound represented by the formula (1) may have one or more isomers selected from the group consisting of asymmetric atoms, geometric isomers, and one or two axial chiralities. In this case, the isomer ratio may be a single isomer or a mixture ratio of any proportion, and is not particularly limited.

[0069] The compound represented by formula (1) may form a salt. The salt of the compound represented by formula (1) is not particularly limited as long as it does not impair the effects of the invention, and examples thereof include hydrochloride, sulfate, acetate, fumarate, maleate, and metal salts such as sodium salt, potassium salt, and calcium salt.

[0070] A group in which Q in the above formula (1) has a nitrogen-containing ring structure represented by formula (Q1) can be synthesized using a synthesis method for a 2-pyridone compound described in WO 2017 / 061525, WO 2018 / 139560, etc. A group in which Q in the above formula (1) has a nitrogen-containing ring structure represented by formula (Q2) can be synthesized using a synthesis method for a pyridazine compound described in WO 2005 / 121104, etc. A group in which Q in the above formula (1) has a nitrogen-containing ring structure represented by formula (Q3) can be synthesized using a synthesis method for a pyrazole compound described in WO 2012 / 031061, etc.

[0071] Specific examples of the compound represented by the above formula (1) (compounds 1 to 80) are shown in the following Tables 1 to 8. In Tables 1 to 8, "Me" represents a methyl group.

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080] <Other Components> The composition of the present embodiment may contain, in addition to the compound represented by formula (1) (hereinafter, sometimes simply referred to as the "compound of the present embodiment"), a carrier, an adjuvant, etc. The composition of the present embodiment may also be formulated.

[0081] [Carrier] In the composition of this embodiment, the compound of this embodiment may be used as is, but is usually used in combination with a carrier.

[0082] The carrier used in the composition of this embodiment refers to a synthetic or natural inorganic or organic substance that is incorporated to help the compound of this embodiment reach the site where the control effect is to be exerted and to facilitate the storage, transportation, and handling of the compound of this embodiment. In the composition of this embodiment, any solid, liquid, or gas carrier typically used in pesticides can be used. The carrier is not particularly limited as long as the control effect of the compound of this embodiment is exerted.

[0083] Examples of solid carriers that can be used in the composition of this embodiment include inorganic substances such as bentonite, montmorillonite, diatomaceous earth, white clay, talc, and clay; plant-derived organic substances such as wood flour and sawdust; and urea.

[0084] Examples of liquid carriers that can be used in the composition of the present embodiment include aromatic hydrocarbons such as xylene and toluene, aliphatic hydrocarbons such as naphthenes, n-paraffin, and liquid paraffin, ketones such as acetone and methyl ethyl ketone, ethers such as dioxane and diethylene glycol dimethyl ether, alcohols such as ethanol and ethylene glycol, carbonates such as ethylene carbonate, aprotic solvents such as dimethylformamide, animal fats and oils such as whale oil, shark oil, liver oil, beef tallow, lard, and milk fat, vegetable oils and oils such as olive oil, palm oil, castor oil, soybean oil, rapeseed oil, and methylated seed oils derived from vegetable oils, essential oils such as orange oil and lemon oil, and water.

[0085] Examples of gas carriers that can be used in the composition of this embodiment include nitrogen and carbon dioxide gas.

[0086] [Adjuvants] If necessary, the composition of the present embodiment may contain adjuvants such as surfactants, binders, disintegrants, stabilizers, pH adjusters, antibacterial and antifungal agents, thickeners, antifoaming agents, antifreeze agents, etc. The adjuvants used in the composition of the present embodiment are not particularly limited as long as the effects of the present embodiment are exhibited.

[0087] The adjuvants can be used alone or in combination depending on the purpose, taking into consideration the dosage form of the preparation, the processing method, etc.

[0088] Surfactants can generally be used for the purposes of emulsifying, dispersing, spreading, wetting, etc. of pesticide formulations. Examples of such surfactants include nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants.

[0089] Examples of nonionic surfactants include sorbitan fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene polyoxypropylene block polymers, alkyl polyoxyethylene polyoxypropylene block polymer ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene bisphenyl ethers, polyoxyalkylene adducts of higher alcohols, polyoxyethylene ethers, ester-type silicones, and fluorine-based surfactants.

[0090] Examples of anionic surfactants include alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene benzyl phenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, paraffin sulfonates, alkanesulfonates, AOS, dialkyl sulfosuccinates, alkylbenzene sulfonates, lignin sulfonates, polyoxyethylene alkyl phenyl ether sulfonates, fatty acid salts, N-methyl-fatty acid sarcosinates, polyoxyethylene alkyl ether phosphates, polyoxyethylene phenyl ether phosphates, polyoxyethylene polyoxypropylene block polymer phosphates, phosphatidylcholines, phosphatidylethanolimines, alkyl phosphates, and sodium tripolyphosphate.

[0091] Examples of cationic surfactants include alkyltrimethylammonium chloride, alkyldimethylbenzalkonium chloride, and benzethonium chloride.

[0092] Examples of amphoteric surfactants include dialkyldiaminoethylpentaine and alkyldimethylbenzylpentaine.

[0093] Binders include sodium alginate, polyvinyl alcohol, gum arabic, sodium carboxymethyl cellulose, and bentonite.

[0094] Disintegrants include carboxymethylcellulose CMC sodium and croscarmellose sodium.

[0095] Examples of the stabilizer include hindered phenol-based antioxidants, and benzotriazole-based or hindered amine-based ultraviolet absorbers.

[0096] Examples of pH adjusters include phosphoric acid, acetic acid, and sodium hydroxide.

[0097] Examples of antibacterial and antifungal agents include sodium benzoate, potassium sorbate, parahydroxybenzoic acid esters, and 1,2-benzisothiazolin-3-one.

[0098] Thickeners include xanthan gum, guar gum, sodium carboxymethylcellulose, gum arabic, polyvinyl alcohol, and montmorillonite.

[0099] The antifoaming agent may be a silicone compound or the like.

[0100] Examples of antifreeze agents include propylene glycol and ethylene glycol.

[0101] [Formulation] The composition of this embodiment can be formulated into a wettable powder, flowable powder, water dispersible granule, OD agent, liquid, emulsifiable concentrate, dust, granule, fine granule, etc. according to a conventional method. The form is not particularly limited as long as the control effect of the composition of this embodiment is exhibited. Specific formulation examples are shown below, but are not limited to these and can be produced using known formulation manufacturing methods. Note that the blending parts of each component described in the following formulation examples all refer to parts by mass.

[0102] Formulation Example 1: Flowable Preparation A compound of the present embodiment (10 parts by mass), a formaldehyde condensate sodium salt of naphthalenesulfonic acid (5 parts by mass), polyoxyethylene arylphenyl ether (1 part by mass), propylene glycol (5 parts by mass), a silicone antifoaming agent (0.1 part by mass), xanthan gum (0.2 parts by mass), and ion-exchanged water (78.7 parts by mass) are mixed to form a slurry, which is then wet-pulverized using DYNOMILL KDL (trade name, manufactured by Willy & Bachofen) with glass beads having a diameter of 1.0 mm to obtain a flowable preparation.

[0103] (Formulation Example 2: Emulsion) The compound of this embodiment (5 parts by mass) is dissolved in a mixed solution of xylene (40 parts by mass) and cyclohexane (35 parts by mass), and Tween 20 (20 parts by mass) is added to and mixed with this solution to obtain an emulsion.

[0104] (Formulation Example 3: Wettable Powder) The compound of this embodiment (10 parts by mass), white carbon (10 parts by mass), polyvinyl alcohol (2 parts by mass), dioctyl sulfosuccinate sodium salt (0.5 parts by mass), alkylbenzenesulfonate sodium salt (5 parts by mass), calcined diatomaceous earth (10 parts by mass) and kaolinite clay (62.5 parts by mass) are thoroughly mixed and pulverized in a jet mill to obtain a wettable powder.

[0105] Formulation Example 4: Dust A compound of the present embodiment (0.3 parts by mass), polyoxyethylene glycol (0.4 parts by mass), white carbon (0.3 parts by mass), calcium carbonate (66.0 parts by mass), and clay (33.0 parts by mass) are mixed, and the resulting mixture is pulverized with a hammer mill to obtain a dust.

[0106] (Formulation Example 5: Granules) Ion-exchanged water is added to the compound of this embodiment (2 parts by mass), sodium tripolyphosphate (2 parts by mass), alkyl sulfosuccinate salt (0.2 parts by mass), glucan (1.5 parts by mass), bentonite (25 parts by mass), and calcium carbonate (69.3 parts by mass) and mixed. The resulting mixture is then extruded and granulated using a Dome Gran (extrusion granulator). The resulting granules are then dried in a tray dryer to obtain granules.

[0107] (Formulation Example 6: Microgranules) The compound of this embodiment (0.3 parts by mass), polyoxyethylene rosinate (0.1 parts by mass), polyethylene glycol (0.25 parts by mass), and calcium carbonate (99.35 parts by mass) are mixed using a mixer (KENMIX (registered trademark) chef) to obtain microgranules.

[0108] The content of the compound of this embodiment in the composition is not particularly limited as long as the effect is exhibited, but is usually in the range of 0.01 to 99% by mass. In particular, for wettable powders, flowable formulations, water dispersible granules, OD formulations, liquid formulations, and emulsifiable concentrates, the range of 5 to 80% by mass is preferred, and for dusts and fine granules, the range of 0.1 to 5% by mass is preferred.

[0109] The compound of this embodiment can be mixed with a fertilizer and an agricultural chemical containing a compound other than the compound of this embodiment as an active ingredient, as needed, to prepare a pest control composition. Examples of the fertilizer and the agricultural chemical include fungicides, insecticides, miticides, nematicides, herbicides, biological pesticides, and plant growth regulators.

[0110] Furthermore, the composition of the present embodiment can be mixed or used in combination with a pesticide containing a compound other than the compound of the present embodiment as an active ingredient, a disease control agent containing a nucleic acid as an active ingredient, a soil improver, or a fertilizer, as needed.

[0111] <Control Method> A method for controlling plant diseases caused by Porphyromonas using the composition of this embodiment includes applying the composition to plants, plant seeds, or the soil in which plants are grown.

[0112] The method of applying the composition of the present embodiment to plants, plant seeds, or the soil in which plants are grown is not particularly limited, and examples include spraying the stems and leaves of plants, treatment on cell trays, treatment on paper pots, spraying on the soil surface, soil incorporation after spraying on the soil surface, injection into the soil, soil incorporation after injection into the soil, soil drench, soil incorporation after soil drench, plant immersion, spraying on plant seeds, smearing on plant seeds, immersion on plant seeds, and dressing on plant seeds.

[0113] More specifically, spraying of wettable powders, flowable powders, wettable powder granules, OD agents, liquid agents, emulsions, or dilutions thereof onto plants before planting, spraying of foliage onto plants after sowing or planting, drenching onto cell trays or paper pots before planting, spraying onto the entire soil of a field before sowing or planting, spraying onto the entire soil of a field before sowing or planting and then mixing, spraying into planting furrows of a field at the time of sowing or planting, and spraying into planting holes of a field at the time of sowing or planting. Examples of the treatments include, but are not limited to, irrigation treatment, spraying treatment on the soil after sowing, irrigation treatment on plants after planting, drip irrigation treatment on plants after sowing or planting, root immersion treatment on plants before planting, smearing treatment on seeds before sowing, flash immersion treatment on seeds before sowing, soil incorporation of dusts, granules and microgranules into the soil used for raising seedlings, overall soil incorporation into the field before planting, row incorporation into the field before planting, and dust coating treatment on seeds.

[0114] The drip irrigation treatment refers to applying the composition of the present embodiment or a diluted solution thereof to soil or plants using a drip irrigation system used during cultivation. The cell trays and paper pots refer to those containing seedling soil or those containing seedling soil and plants grown therein. The soil refers to the soil in which plants are grown in a field, as well as the soil and culture medium used for seedling cultivation.

[0115] In the control method of this embodiment, the application amount and dilution ratio of the composition of this embodiment can be appropriately selected depending on the target plant, target pest, level of pest infestation, formulation of the composition of this embodiment, application method, various environmental conditions, etc.

[0116] When the composition of the present embodiment is applied to a field, the application amount is not particularly limited as long as the effect is exhibited, and is usually 1 to 10,000 g per hectare, preferably 10 to 5,000 g per hectare, in terms of the amount of active ingredient.

[0117] When the composition of the present embodiment is applied to seeds, the application amount is not particularly limited as long as the effect is exhibited. The amount is usually 0.001 to 100 g, preferably 0.01 to 50 g, of the active ingredient per kg of seeds.

[0118] When the composition of the present embodiment is used in the form of a wettable powder, water dispersible granule, liquid formulation, OD formulation, flowable formulation, or emulsifiable concentrate, the dilution ratio is not particularly limited as long as the desired effect is exhibited, and is typically 5 to 50,000 times, and preferably 10 to 10,000 times.

[0119] Specific examples of plants that can be treated with the plant disease control method of this embodiment include cabbage (Brassica oleracea var. capitata), Brussels sprouts (Brassica oleracea var. gemmifera), Chinese cabbage (Brassica rapa var. pekinensis), broccoli (Brassica oleracea var. italica), cauliflower (Brassica oleracea var. botrytis), Romanesco (Brassica oleracea var. botrytis), and turnip (Brassica rapa subsp. rapa), Komatsuna (Brassica rapa var. perviridis), Nozawana (Brassica rapa var. hakabura), Bok choy (Brassica rapa subsp. chinensis), Tatsoi (Brassica rapa subsp. narinosa), Oilseed rape (Brassica rapa var. nippo-oleifera), European rape (Brassica napus), Takana (Brassica juncea var. integrofolia), Mizuna (Brassica rapa subsp. japonica), mibuna (Brassica rapa var. laciniifolia subvar. oblanceolata), Mizukakena (Brassica rapa), collard greens (Brassica oleracea var. viridis), kale (Brassica oleracea var. sabellica), kohlrabi (Brassica oleracea var. gonygylodes), mustard (Brassica juncea), rutabaga (Brassica napus var. napobrassica), arugula (Eruca spp.) belonging to the genus Eruca vesicaria subsp. sativa), horseradish (Armoracia rusticana) belonging to the genus Armoracia, wasabi (Eutrema japonicum) belonging to the genus Eutrema,Cruciferous crops such as watercress (Nasturtium officinale) belonging to the genus Nasturtium and radish (Raphanus sativus var. hortensis) belonging to the genus Raphanus; Amaranthaceae crops such as sugar beet (Beta vulgaris subsp. vulgaris); Solanaceae crops such as potato (Solanum tuberosum), tomato (Solanum lycopersicum), eggplant (Solanum melongena), and nightshade (Solanum nigrum); rice (Oryza sativa), wheat (Triticum aestivum), barley (Hordeum vulgare), and corn (Zea mays); The above plants also include, but are not limited to, F1 varieties of these plants and genetically modified crops that are not naturally occurring and are produced by artificially manipulating genes.

[0120] From the viewpoint that the composition of the present embodiment has a superior control effect among the above-mentioned plants, the target crop of the plant disease control method is preferably at least one selected from the group consisting of crops belonging to the Brassicaceae family, the Solanaceae family, and the Poaceae family, and more preferably at least one selected from the group consisting of crops belonging to the genus Brassica, crops belonging to the Solanaceae family, wheat, and barley.

[0121] Seeds that are the target of the plant disease control method of this embodiment include, for example, seeds of Brassicaceae crops, Gramineae crops, Solanaceae crops, and sugar beets, and seed potatoes such as potatoes, but are not limited to these.

[0122] In this specification, "Pycnophora" refers to fungi belonging to the kingdom Protozoa, phylum Cercozoa, class Phytomyxa, order Pycnophorales, and family Pycnophoridae, and "plant diseases caused by Pycnophora" refers to plant diseases caused by Pycnophora infecting plants, and plant diseases caused by Pycnophora transmitting pathogenic viruses.

[0123] Plant diseases caused by Plasmodiophora species that are the target of control by the composition of this embodiment include plant diseases caused by fungi of the genera Plasmodiophora, Spongospora, and Polymyxa. Specific plant diseases include, but are not limited to, clubroot of cruciferous crops caused by Plasmodiophora brassicae, potato powdery scab caused by Spongospora subterranea, potato tuber brown ring spot caused by Spongospora subterranea transmitting a pathogenic virus, sugar beet root disease caused by Polymyxa betae transmitting a pathogenic virus, and wheat yellow mosaic, barley yellow mosaic, and wheat-like dwarf disease caused by Polymyxa graminis transmitting a pathogenic virus. Among these, as will be shown in the examples described later, the plant diseases caused by the genus Plasmodiophora that are the target of control by the composition of this embodiment are preferably clubroot of cruciferous crops, powdery scab of potato, wheat yellow mosaic disease, barley yellow mosaic disease, and wheat-borne dwarf disease.

[0124] The effectiveness of the compound of this embodiment against plant diseases caused by P. cerevisiae will be specifically demonstrated below by way of test examples, although the content of this embodiment is not limited to these test examples.

[0125] [Test Compounds] The test compounds used in this test example were Compounds 1 to 80 shown in Tables 1 to 8 above, and Comparative Examples 1 to 3 shown in Table 9 below. Compounds 1 to 80 are compounds of the present embodiment. In Table 9, Comparative Example 1 is metalaxyl-M (CAS number: 70630-17-0), Comparative Example 2 is inpirfluxam (CAS number: 1352994-67-2), and Comparative Example 3 is picarbutrazox (CAS number: 500207-04-5). In Table 9, "Me" represents a methyl group.

[0126]

[0127] Test Example 1: Control effect against clubroot of Chinese cabbage A dimethyl sulfoxide solution of the test compound was diluted with well water to a test compound concentration of 200 ppm by mass, thereby obtaining a chemical solution for irrigation.

[0128] Next, Chinese cabbage (variety: Nozaki No. 2) seeds were sown in nursery soil, and 6 days after sowing, 3 ml of a resting spore suspension (1,000,000 / ml) of Plasmodiophora brassicae, a pathogen of clubroot disease of Brassicaceae crops, was irrigated at the base of the test plants. Two hours after irrigation with the resting spore suspension, 3 ml of the irrigation solution was irrigated at the base of the test plants (drug-treated test area). In addition, the untreated test area was treated in the same way as the drug-treated test area with well water prepared to contain the same mass of dimethyl sulfoxide as the drug-treated test area.

[0129] After the treatment, the test plants were kept in an incubator at a room temperature of 23°C (16 hours light, 8 hours dark cycle), and the degree of disease development was examined 24 days after treatment. Four plants were treated in each test plot.

[0130] (Disease severity) The severity of disease 24 days after treatment was scored as 0 for no disease, 1 for galls observed on the subroots but no disease observed on the taproot, 2 for small galls observed on the taproot, and 3 for large galls observed on the taproot, with the average of the four plants being the severity of disease for each test plot. The results of the disease severity are shown in Table 10.

[0131] (Control Value) Using n as the disease severity in each test plot, the control value was calculated according to the following formula. The control value results are shown in Table 10. Control value = 100 × {1 - (n / disease severity in untreated test plot)} This test demonstrated that the composition of the present embodiment has a high control effect against clubroot of cruciferous crops.

[0132]

[0133] As shown in Table 10, it was revealed that the composition containing the compound of this embodiment has an excellent control effect against plant diseases caused by Porphyromonas spp.

[0134] Test Example 2: Infection inhibitory effect against potato powdery scab pathogen (Spongospora subterranea) Tomato seeds (variety: Large Fukuju) were sown in nursery soil, and 12 days after sowing, 3 ml of a spore ball suspension (100,000 spore balls / ml) of potato powdery scab pathogen (Spongospora subterranea) was irrigated at the base of the test plants.

[0135] Next, the dimethyl sulfoxide solution of the test compound was diluted with well water to a test compound concentration of 200 ppm by mass to obtain a chemical solution for irrigation. Two hours after the irrigation of the resting spore suspension, 3 ml of the chemical solution for irrigation was irrigated at the base of the test plants (chemical treatment test group). Note that the chemical-untreated test group was treated in the same manner as the chemical-treated test group with well water prepared to contain the same mass of dimethyl sulfoxide as the chemical-treated test group.

[0136] After the chemical treatment, the test plants were kept in an incubator at a room temperature of 23°C (16-hour light / 8-hour dark cycle). 17 days after treatment, the roots of each plant were thoroughly washed, and a section 2 to 5 cm from the base of the root was cut into 5 mm pieces. Five randomly selected roots were observed under a microscope to count the number of infected areas with Spongospora subterranea. Four plants were treated in the same way for each test plot, and the average of the four plants was used to count the number of infected areas for each test plot.

[0137] (Control Titer) The control titer was calculated according to the following formula, where n is the number of infected sites in each test plot. The control titer results are shown in Table 11. Control titer = 100 × {1 - (n / number of infected sites in untreated plot)} This test demonstrated that the composition of the present embodiment has a high infection inhibitory effect against the potato powdery scab pathogen (Spongospora subterranea). Tomatoes were used as test plants in this test, but potato powdery scab is known to infect Solanaceae plants such as potato, tomato, and eggplant, and the infection mode of Spongospora subterranea is the same in potato and tomato, so it is thought that the composition will also be highly effective on potato.

[0138]

[0139] Test Example 3: Infection-inhibiting effect on Polymyxa graminis A dimethyl sulfoxide solution of the test compound was diluted with well water to a test compound concentration of 200 ppm by mass, thereby obtaining a medicinal solution for irrigation.

[0140] Next, wheat seeds (cultivar: Kitahonami) were sown in soil contaminated with wheat dwarf disease containing Polymyxa graminis. Immediately after sowing, 5 ml of the irrigation solution was irrigated at the seeding site (fungicide-treated test area). The untreated test area was treated in the same manner as the treated test area with well water prepared to contain the same mass of dimethyl sulfoxide as the treated test area.

[0141] After the chemical treatment, the test plants were kept in an incubator at a room temperature of 15°C (16-hour light, 8-hour dark cycle). 61 days after treatment, the roots of each plant were thoroughly washed, and a section 2-5 cm from the base of the root was cut into 5 mm pieces. Ten randomly selected roots were observed under a microscope and the number of Polymyxa graminis infection sites was counted. Three plants were treated in the same way for each test plot, and the average of the three plants was used as the number of infection sites for each test plot.

[0142] (Control Titer) The control titer was calculated according to the following formula, where n is the number of infected sites in each test plot. The control titer results are shown in Table 12. Control titer = 100 × {1 - (n / number of infected sites in untreated plot)} This test demonstrated that the composition of the present embodiment has a high infection inhibitory effect against Polymyxa graminis. Wheat yellow mosaic disease, barley yellow mosaic disease, and wheat pseudomosaic disease are all caused by pathogenic viruses transmitted by Polymyxa graminis. Therefore, the composition of the present embodiment, which has a high infection inhibitory effect against Polymyxa graminis, is considered to be highly effective against all of wheat yellow mosaic disease, barley yellow mosaic disease, and wheat pseudomosaic disease. In this test, wheat was used as the test plant, but since the infection mode of Polymyxa graminis is the same in wheat and barley, it is thought that the compound will also be highly effective in barley.

[0143]

[0144] The composition for controlling plant diseases caused by Porphyromonas spp. of the present embodiment and the control method using the composition for controlling plant diseases have excellent control effects, and are therefore useful as agricultural chemicals.

Claims

1. A composition for controlling plant diseases caused by Porphyromonas spp., which contains a compound represented by formula (1) or a salt thereof. [In the formula, Ar1 represents a phenyl group that is unsubstituted or substituted with n R1 groups. R1 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, or a cyano group. n represents an integer of 1 to 5. However, when n is an integer of 2 or greater, multiple R1 groups may be the same or different. Ar2 represents a phenyl group that is unsubstituted or substituted with m R2 groups. R2 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, or a cyano group. m represents an integer of 1 to 5. However, when m is an integer of 2 or greater, multiple R2 groups may be the same or different. X represents -NH- or a direct bond. Q represents a group having a nitrogen-containing ring structure represented by any of the following formulae (Q1) to (Q3).] [In the formula, A represents Ar1 in the formula (1). B represents X-Ar2 in the formula (1). R3 represents a hydrogen atom, a chlorine atom, a methyl group, an ethyl group, or a normal propyl group. R4 represents a methyl group, an ethyl group, or a difluoroethyl group.] [In the formula, A represents Ar1 in the formula (1). B represents X-Ar2 in the formula (1). R5 represents a hydrogen atom, a chlorine atom, a methyl group, an ethyl group, or a normal propyl group. R6 represents a chlorine atom, a methyl group, an ethyl group, or a difluoroethyl group.] [In the formula, A represents Ar1 in the formula (1). B represents X-Ar2 in the formula (1). R7 represents a hydrogen atom, a chlorine atom, a methyl group, an ethyl group, or a normal propyl group. R8 represents a methyl group, an ethyl group, or a difluoroethyl group.] 2. A composition for controlling plant diseases caused by Porphyromonas spp. according to claim 1, wherein the compound represented by formula (1) is a compound represented by the following formula (1-1): [In the formula, Ar1 represents a phenyl group that is unsubstituted or substituted with n R1 groups. R1 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, or a cyano group. n represents an integer of 1 to 5. However, when n is an integer of 2 or greater, multiple R1 groups may be the same or different. Ar2 represents a phenyl group that is unsubstituted or substituted with m R2 groups. R2 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, or a cyano group. m represents an integer of 1 to 5. However, when m is an integer of 2 or greater, multiple R2 groups may be the same or different. R3 represents a hydrogen atom, a chlorine atom, a methyl group, an ethyl group, or a normal propyl group. R4 represents a methyl group, an ethyl group, or a difluoroethyl group.] 3. A composition for controlling plant diseases caused by Porphyromonas spp. according to claim 1, wherein the compound represented by formula (1) is a compound represented by the following formula (1-2): [In the formula, Ar1 represents an unsubstituted phenyl group, and Ar2 represents a phenyl group substituted with two fluorine atoms.] 4. A composition for controlling plant diseases caused by Porphyromonas spp. according to claim 3, which contains a compound represented by the following formula (2) or a salt thereof:

5. A composition for controlling plant diseases caused by Porphyromonas spp. according to claim 1, wherein the compound represented by formula (1) is a compound represented by the following formula (1-3): [In the formula, Ar1 represents a phenyl group substituted with two R1. R1 represents a fluorine atom or a bromine atom. The two R1 may be the same or different. Ar2 represents a phenyl group substituted with two R2. R2 represents a fluorine atom or a chlorine atom. The two R2 may be the same or different.] 6. A composition for controlling plant diseases caused by P. cerevisiae according to claim 5, which contains a compound represented by the following formula (3) or a salt thereof:

7. A composition for controlling plant diseases caused by Phytophthora spp. according to any one of claims 1 to 6, wherein the plant diseases caused by Phytophthora spp. are clubroot of cruciferous crops, powdery scab of potato, wheat yellow mosaic disease, barley yellow mosaic disease, and wheat-borne dwarf disease.

8. A method for controlling plant diseases caused by P. cerevisiae, which comprises applying the composition according to claim 1 to plants, plant seeds, or the soil in which plants are grown.

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