JP2016179944A - Difluoromethylene compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a plant disease controlling agent that exhibits high controlling effect on a wide range of plant pathogenic microbes without depending on the application site.SOLUTION: The present invention provides an aminoquinazoline compound or an aminopyrimidine compound or salt thereof, having a difluoromethylene group represented by formula (I), a bactericide for agricultural and horticultural use comprising the compound as an active ingredient, and a plant disease controlling method including the application of the compound [where A is pyrimidine or quinazoline, optionally substituted by X and binds -NH- at 4-position; X is selected from the group of halogen, alkyl and others; B is pyridine, optionally substituted by Y; Y is selected from the group of halogen, alkyl, haloalkyl and others; Ris selected from the group of halogen, alkyl, haloalkyl and others; m is an integer of 0-4].SELECTED DRAWING: None

Description

  The present invention relates to a novel difluoromethylene compound or a salt thereof, an agricultural and horticultural fungicide containing the compound or a salt thereof as an active ingredient, and a plant disease control method using the compound or a salt thereof.

Patent Document 1 describes aminoquinazoline compounds useful as agricultural chemicals and animal health products, but does not disclose a compound having a difluoromethylene group. Further, diflumetrim (generic name), which is an aminopyrimidine compound, is used as an agricultural and horticultural fungicide, which also has no difluoromethylene group.
Thus, an aminoquinazoline compound or aminopyrimidine compound having a difluoromethylene group that is useful as an agricultural and horticultural fungicide is not known.

International Publication No. WO2010 / 025451

The Pesticide Manual (16th edition; BRITISH CROP PROTECTION COUNCIL) 358-359

  Conventionally, many drugs provided for controlling plant diseases are each characterized in their spectrum and plant pathogen control effect. For example, the effect on specific plant diseases is not sufficient, the treatment effect is slightly inferior to the preventive effect, or the rain resistance is inferior or the residual effect is relatively short, depending on the application scene, It may show only practically insufficient control effects against plant pathogens. Therefore, creation of a plant disease control agent that exhibits a high control effect on a wide range of plant pathogens regardless of the application situation is desired.

  As a result of researches to solve the above-mentioned problems, the present inventors have a useful property as an agricultural and horticultural fungicide, which is a compound represented by the formula (I) having a difluoromethylene group or a salt thereof, The present invention was completed by obtaining the knowledge that an excellent control effect was exhibited against various plant diseases.

  That is, the present invention relates to the formula (I):

[Where:
A is pyrimidine or quinazoline, optionally substituted with X;
X is selected from the group consisting of halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, cycloalkyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio and haloalkylthio;
B is pyridine optionally substituted with Y;
Y is selected from the group consisting of halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio and haloalkylthio;
R ¹ is selected from the group consisting of halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio and haloalkylthio;
m is an integer of 0 to 4]
Or a salt thereof (hereinafter also referred to as the compound of the present invention), an agricultural and horticultural fungicide containing the compound of the present invention as an active ingredient, and a method for controlling plant diseases applying the compound of the present invention.

  The compound of the present invention has a high control effect against a wide range of plant pathogens.

  In the present specification, unless otherwise specified, examples of the halogen or the halogen as a substituent include fluorine, chlorine, bromine and iodine. The number of halogens as a substituent may be 1 or 2 or more, and in the case of 2 or more, each halogen may be the same or different. Further, the halogen substitution position may be any position.

In the present specification, unless otherwise specified, the alkyl or alkyl moiety may be linear or branched, and specific examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl. , C _1-8 such as pentyl, hexyl, heptyl and octyl.

In the present specification, unless otherwise specified, the alkenyl or alkenyl moiety may be linear or branched, and specific examples thereof include vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, Examples include C _2-6 such as 1,3-butadienyl and 1-hexenyl.

In the present specification, unless otherwise specified, examples of cycloalkyl include C _3-6 such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.

  The bonding position between the pyrimidine or quinazoline represented by A in formula (I) and —NH— is not particularly limited, but it is preferable to bond to —NH— at the 4-position of pyrimidine or quinazoline. As a preferable specific example of the bonding position of pyrimidine or quinazoline represented by A and —NH—,

Is mentioned.

  The pyrimidine or quinazoline represented by A may be substituted with X. When the pyrimidine is substituted with X, the number of substitutions is 1 to 3. When the quinazoline is substituted with X, the number of substitutions is 1-5. Further, when substituted with a plurality of X, X may be the same or different.

  Examples of pyridine represented by B in formula (I) include 2-pyridine, 3-pyridine and 4-pyridine, and 2-pyridine is preferred.

  The pyridine represented by B may be substituted with Y, and the number of substitutions is 1 to 4. Further, when substituted with a plurality of Y, Y may be the same or different.

When m is 2 or more, two or more R ¹ may be the same or different.

  The salt of the compound of the formula (I) includes any salt that is acceptable in the technical field. For example, a salt with an inorganic acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or the like. Salts with organic carboxylic acids such as tartaric acid, formic acid, acetic acid, citric acid, fumaric acid, maleic acid, trichloroacetic acid and trifluoroacetic acid; methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, mesitylenesulfonic acid and naphthalene And salts with sulfonic acids such as sulfonic acids.

  The compound of the present invention may have isomers such as geometric isomers, tautomers and optical isomers, and the present invention includes both isomers and isomer mixtures. In the present specification, unless otherwise specified, isomers are described as a mixture. The present invention also includes various isomers other than those described above within the scope of technical common sense in the technical field.

  Depending on the type of isomer, the chemical structure may differ from the described structural formula, but those skilled in the art can fully recognize that these are related to the isomer, and therefore are within the scope of the present invention. Obviously.

  Desirable embodiments of the compound of the present invention include the following compounds, but the compound of the present invention is not limited thereto.

Compound (IA)
A is a pyrimidine or quinazoline optionally substituted with X, bonded to —NH— at the 4-position thereof;
X is selected from the group consisting of halogen, alkyl and haloalkyl;
B is 2-pyridine, 3-pyridine or 4-pyridine substituted with Y;
Y is selected from the group consisting of halogen, alkyl and haloalkyl;
R ¹ is selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano and alkoxycarbonyl;
m is an integer from 0 to 2;
A compound of the above formula (I) or a salt thereof.

Compound (IB)
A is a pyrimidine or quinazoline optionally substituted with X, bonded to —NH— at the 4-position thereof;
X is selected from the group consisting of halogen, alkyl and haloalkyl;
B is 2-pyridine substituted with Y;
Y is haloalkyl;
R ¹ is halogen;
m is 0 or 1;
A compound of the above formula (I) or a salt thereof.

Compound (IC)
A is unsubstituted quinazoline, bonded to —NH— at its 4-position;
B is 2-pyridine substituted with Y;
Y is haloalkyl;
m is 0;
A compound of the above formula (I) or a salt thereof.

  Although this invention compound can be manufactured in accordance with the following manufacturing methods and the manufacturing method of a normal salt, it is not limited to these methods.

Manufacturing method [1]
The compound of the present invention can be produced by the following production method [1].

In the formula, A, B, R ¹ and m are as described above, and X ¹ is halogen (chlorine, bromine, iodine, etc.).

  The compound of Formula (III) can be used in the ratio of 1-50 equivalent with respect to 1 equivalent of compounds of Formula (II), desirably 1-5 equivalent.

  This reaction can usually be performed in the presence of a base. The base is not particularly limited as long as the reaction proceeds. For example, alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate; alkalis such as calcium carbonate And earth metal carbonates; organic amines such as triethylamine, pyridine, 4- (N, N-dimethylamino) pyridine; and the like. A base can be used in the ratio of 1-20 equivalent with respect to 1 equivalent of compounds of Formula (III), desirably 1-5 equivalent.

  This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; diethyl ether, diisopropyl ether and dibutyl ether , Tetrahydrofuran, dioxane, ethers such as ethylene glycol dimethyl ether; nitriles such as acetonitrile and propionitrile; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane; N, N -Acid amides such as dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidinone; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; hexamethylphosphor Phosphoric acid amides such as de; and one from and mixtures of these solvents or but two or more can be selected appropriately, among them acid amides are preferred.

  The reaction temperature is usually 0 ° C to 200 ° C, desirably 70 ° C to 120 ° C. The reaction time is usually 1 to 48 hours.

Manufacturing method [2]
The compound of the formula (II) can be produced by the following production method [2].

In the production method [2], B, R ¹ and m are as described above, and L is halogen (chlorine, bromine, iodine, etc.) or OSO ₂ R ^A (R ^A is methyl, 4-methylphenyl, etc.) ).

  A compound of formula (V) can be produced by reacting potassium phthalimide with a compound of formula (IV) (step [2-1]).

  Potassium phthalimide can be used in a proportion of 1 to 50 equivalents, preferably 2 to 10 equivalents, relative to 1 equivalent of the compound of formula (IV).

  The reaction of step [2-1] can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, aromatic hydrocarbons such as benzene, toluene and xylene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, and diethylene glycol dimethyl ether; Acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidinone; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; dimethyl sulfoxide 1 type or 2 or more types can be appropriately selected from such sulfoxides; sulfones such as sulfolane; phosphoric amides such as hexamethylphosphoramide; and mixed solvents thereof, among which acid amides are preferable. .

  The reaction temperature is usually 0 ° C to 200 ° C, preferably 70 ° C to 150 ° C. The reaction time is usually 1 to 48 hours.

  A compound of formula (II) can be produced by reacting formula (V) with hydrazines (step [2-2]).

  Examples of hydrazines include hydrazine hydrate (hydrazine monohydrate), methyl hydrazine and the like. Hydrazines can be used in a proportion of 2 to 50 equivalents, preferably 2 to 10 equivalents, relative to 1 equivalent of the compound of formula (V).

  The reaction of step [2-2] can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; diethyl ether, diisopropyl ether, tetrahydrofuran, Ethers such as dioxane, dimethoxyethane, diethylene glycol dimethyl ether; acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidinone; chloroform, dichloromethane, carbon tetrachloride, 1,2- Halogenated hydrocarbons such as dichloroethane; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; phosphoric acid amides such as hexamethylphosphoramide; and mixed solvents thereof One or more of can be selected as appropriate but, among them alcohol is desirable.

  The reaction temperature is usually 0 ° C to 200 ° C, desirably 70 ° C to 120 ° C. The reaction time is usually 1 to 48 hours.

Manufacturing method [3]
The compound of the formula (IV) can be produced by the following production method [3].

In the production process [3], B, R ¹ , m and L are as described above.

In the production method [3], a compound (IV) in which L is a halogen can be produced by halogenating a compound of the formula (VI), and by sulfonylating the compound of the formula (VI), L is converted to OSO. Compound (IV) which is ₂ R ^A (R ^A is as described above) can be produced.

  The halogenation in the production method [3] can be performed in the presence of a halogenating agent, a phosphine and a base.

  Examples of the halogenating agent that can be used include chlorine, bromine, and iodine. The halogenating agent can be used in a proportion of 1 to 50 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (VI).

  Examples of phosphines that can be used include triphenylphosphine. The phosphine can be used at a ratio of 1 to 50 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (VI).

  Examples of the base that can be used include imidazole. The base is used in a proportion of 1 to 50 equivalents, preferably 2 to 5 equivalents, relative to 1 equivalent of the compound of formula (VI).

  The halogenation can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, ligroin and petroleum benzine. Ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; esters such as methyl acetate and ethyl acetate; nitriles such as acetonitrile and propionitrile; N, N-dimethylformamide, N , N-dimethylacetamide, acid amides such as N-methylpyrrolidinone; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; phosphoric amides such as hexamethylphosphoramide; chloroform, dichloromethane, Carbon chloride Halogenated hydrocarbons such as 1,2-dichloroethane; and although one or more kinds of these mixed solvents can be appropriately selected, among others aromatic hydrocarbons, nitriles desirable.

  The reaction temperature is usually 0 ° C to 200 ° C, desirably 70 ° C to 120 ° C. The reaction time is usually 1 to 48 hours.

  The sulfonylation in the production method [3] can be carried out by reacting the compound of the formula (VI) with a sulfonyl halide (such as methanesulfonyl chloride or paratoluenesulfonyl chloride). The sulfonyl halide can be used in a proportion of 1 to 50 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (VI).

  The sulfonylation can usually be performed in the presence of a base. Examples of bases that can be used include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate; alkaline earth metal carbonates such as calcium carbonate; water Alkali metal hydroxides such as sodium oxide and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide; organic amines such as triethylamine, pyridine and 4- (N, N-dimethylamino) pyridine And so on. A base can be used in the ratio of 1-50 equivalent with respect to 1 equivalent of compounds of Formula (VI), 1-5 equivalent desirably.

  The sulfonylation can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, ligroin and petroleum benzine. Ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; esters such as methyl acetate and ethyl acetate; nitriles such as acetonitrile and propionitrile; N, N-dimethylformamide, N , N-dimethylacetamide, acid amides such as N-methylpyrrolidinone; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; phosphoric amides such as hexamethylphosphoramide; chloroform, dichloromethane, Carbon chloride Halogenated hydrocarbons such as 1,2-dichloroethane; and one from and mixtures of these solvents or but two or more can be selected appropriately, inter alia ethers, halogenated hydrocarbons are preferred.

  The reaction temperature is usually 0 ° C to 200 ° C, preferably 20 to 100 ° C. The reaction time is usually 1 to 48 hours.

[Production method 4]
The compound of the formula (VI) can be produced by the following production method [4].

In the production method [4], B, R ¹ and m are as described above, and R ^B is C _1-8 alkyl (methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, octyl, etc. ).

  Production method [4] can be carried out by reducing the compound of formula (VII) with a reducing agent.

  Examples of the reducing agent that can be used in the production method [4] include metal hydrides (such as sodium borohydride and lithium aluminum hydride). The reducing agent can be used in a proportion of 1 to 50 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (VII).

  This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; diethyl ether, diisopropyl ether, tetrahydrofuran, Ethers such as dioxane, dimethoxyethane, diethylene glycol dimethyl ether; acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidinone; chloroform, dichloromethane, carbon tetrachloride, 1,2- One or two or more kinds can be appropriately selected from halogenated hydrocarbons such as dichloroethane; and mixed solvents thereof, among which alcohols are desirable.

  The reaction temperature is usually 0 ° C to 200 ° C, preferably 20 to 70 ° C. The reaction time is usually 1 to 48 hours.

Manufacturing method [5]
The compound of the formula (VII) can be produced by the following production method [5].

PRODUCTION PROCESS [5], ^{B, R} 1, m and ^{R B} are as defined above, X ² is halogen (chlorine, bromine, iodine).

  Production method [5] can be carried out by reacting the compound of formula (VIII) with the compound of formula (IX). The compound of the formula (VIII) can be produced from a commercially available compound by a known method.

  Examples of the compound of formula (IX) used in the production method [5] include ethyl bromodifluoroacetate and ethyl chlorodifluoroacetate. The compound of formula (IX) can be used in a proportion of 1 to 50 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (VIII).

  In the production method [5], metals can be used. Examples of metals that can be used include copper powder and copper salts. The metals can be used in a proportion of 1 to 50 equivalents, preferably 2 to 6 equivalents, relative to 1 equivalent of the compound of formula (VIII).

  This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, aromatic hydrocarbons such as benzene, toluene and xylene; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; methyl acetate Esters such as ethyl acetate; acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; One or two or more types can be selected as appropriate from phosphoric acid amides such as methylphosphoramide; and mixed solvents thereof. Of these, sulfoxides are preferable.

  The reaction temperature is usually 0 ° C to 200 ° C, preferably 20 to 70 ° C. The reaction time is usually 1 to 48 hours.

  The compound of the present invention can be applied to, for example, Mastigomycotina, Ascomycotina, Basidiomycotina, Deuteromycotina, Zygomycotina, etc. Can control plant pathogens to which it belongs.

  More specific examples of the plant pathogenic bacteria include the following.

  As the flagellum subfamily, potato or tomato plague (Phytophthora infestans), tomato gray plague (Phytophthora capsici) genus Phytophthora genus; Pseudoperonospora cubensis Pseudoperonos Pseudoperonospora genus; Plasmopara genus like Plasmopara viticola; Pythium graminicola, Pythium genus like wheat brown snow rot fungus (Pythium iwayamai) And so on.

  As a subfamily of Aspergillus oryzae, the genus Erysiphe such as wheat powdery mildew (Erysiphe graminis); the genus Sphaerotheca such as Sphaerotheca fuliginea and Sphaerotheca humuli ; Uncinula genus such as Uncinula necator; Podosphaera genus such as Podosphaera leucotricha; Mycosphaerella pinodes, Mycosphaerella pomi ), Banana black sigatoka fungus (Mycosphaerella musicola), oyster lobster fungus (Mycosphaerella nawae), Mycosphaerella fragariae, Mycosphaerella genus; Venturia genus such as Venturia nashicola); Pyrenophora teres, Pyrenophora graminea, Pyrenophora genus; Sclerotinia sclerotiorum, Sclerotinia genus; Rice sesame leaf blight (Cochliobolus miya Cochliobolus genus such as); Didymella genus such as Didymella bryoniae; Gibberella genus such as Gibberella zeae; Grape rot fungus (Elsinoe ampelina), the genus Elsinoe like Elsinoe fawcettii; the genus Diaporthe like Diaporthe citri, Diaporthe sp .; Apple Moniria Monilinia mali, Monilinia genus like Monilinia fructicola; grape late rot fungus ( Glomerella cingulata), and the like.

  As a basidiomycete subfamily, Rhizoctonia genus such as rice rot (Rhizoctonia solani); Ustilago genus (Ustilago nuda); Puccinia coronata; Puccinia recondita, Puccinia genus such as wheat yellow rust fungus (Puccinia striiformis);

  As an imperfect subgenus, the genus Septoria such as Septoria nodorum, Septoria tritici; the genus Botrytis such as Botrytis cinerea; Pyricularia genus such as rice blast fungus (Pyricularia oryzae); Cercospora genus such as Cercospora beticola, Cercospora kakivola; Colletotrichum orbiculare Colletotrichum genus such as; Alternaria alternata apple pathotype, Alternaria alternata Japanese pear pathotype, potato summer or Alternaria solani, cabbage black spot fungus ( Alternaria genus such as Alternaria brassicae; Pseudocercosporella herp genus Pseudocercosporella such as otrichoides; genus Pseudocercospora such as Pseudocercospora vitis; Rhynchosporium such as Rhynchosporium secalis Genus; genus Cladosporium such as Cladosporium carpophilum; genus Phomopsis such as Phomopsis sp .; grouse such as Gloeosporium kaki Examples include the genus Gloeosporium; the genus Fulvia such as tomato leaf mold fungus (Fulvia fulva); and the genus Corynespora such as Corynespora cassiicola.

  Examples of the zygomycota include genus Rhizopus such as strawberry soft rot fungus (Rhizopus stronifer) and peach black mold fungus (Rhizopus nigricans).

  The compound of the present invention is useful as an active ingredient of agricultural and horticultural fungicides, such as rice blast, sesame leaf blight, coat blight; wheat powdery mildew, red mold, rust, snow rot , Bare black spot disease, eye spot disease, leaf blight disease, blight disease; citrus black spot disease, common scab; apple monilia disease, powdery mildew, spotted leaf disease, black star disease, anthracnose disease, brown spot disease, Ring rot, soot spot, soot spot, sunspot disease; pear scab, black spot, powdery mildew, plague; pear ring rot, powdery mildew; Homopsis rot; grape black rot, late rot, powdery mildew, downy mildew, gray mold, brown spot, branch rot; oyster anthracnose, defoliation, powdery mildew, soot spot; Anthracnose of cucumber, powdery mildew, vine blight, downy mildew, plague, brown spot; ring tomato, leaf mold, plague, gray mold, powdery mildew; Brassicaceae Downy mildew, black spot disease; potato summer plague, plague; strawberry powdery mildew, gray mold, anthracnose; various crops downy mildew, plague, gray mold, mycorrhizal disease, powdery mildew Although it is effective for controlling diseases such as diseases, it exhibits an excellent control effect especially for the epidemics of fruit trees and vegetables, downy mildew, and blight of wheat. It is also effective in controlling soil diseases caused by phytopathogenic fungi such as Fusarium, Psium, Rhizoctonia, Verticillium, and Plasmodiohora.

  The compound of the present invention is usually prepared by mixing the compound with various agricultural adjuvants, powders, granules, granule wettable powders, wettable powders, aqueous suspensions, oily suspensions, aqueous solvents, emulsions, It can be used in various forms such as liquids, pastes, aerosols, microdispersions, etc., but it can be made into any conventional form used in the art as long as it meets the purpose of the present invention. it can. Adjuvants used in the formulation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch; water , Toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, alcohol, etc. Solvent; fatty acid salt, benzoate, alkylsulfosuccinate, dialkylsulfosuccinate, polycarboxylate, alkylsulfate, alkylsulfate, alkylarylsulfate, alkyldiglycolethersulfate, a Cole sulfate ester salt, alkyl sulfonate salt, alkyl aryl sulfonate salt, aryl sulfonate salt, lignin sulfonate salt, alkyl diphenyl ether disulfonate salt, polystyrene sulfonate salt, alkyl phosphate ester salt, alkyl aryl phosphate salt, styryl Aryl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl aryl phosphate Anionic surfactants such as salts, salt of naphthalene sulfonic acid formalin condensate; sorbitan fatty acid ester, glycerin fatty acid ester, fatty acid polyglyceride Fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, oxyalkylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl aryl ether, polyoxyethylene glycol alkyl ether, polyoxyethylene fatty acid ester, Nonionic surfactants such as polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxypropylene fatty acid ester; olive oil, kapok oil, castor oil, palm oil, palm oil, palm Oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, persimmon oil, liquid paraffin And vegetable oils and mineral oils.

  Each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention. Further, in addition to the above-mentioned adjuvants, it can also be used by appropriately selecting from those known in the art, a bulking agent, a thickener, an anti-settling agent, an antifreezing agent, a dispersion stabilizer, a safener, Various commonly used adjuvants such as antifungal agents can also be used.

  The compounding ratio of the compound of the present invention and various adjuvants is generally 0.005: 99.995 to 95: 5, preferably 0.2: 99.8 to 90:10. Therefore, the content of the arylamidine derivative or a salt thereof in the plant disease control agent is 0.005% to 95% by weight, desirably 0.2% to 90% by weight. In actual use of these preparations, use them as they are or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.

  The concentration of the compound of the present invention varies depending on the target crop, method of use, formulation form, application rate, etc., and cannot be defined unconditionally, but in the case of foliage treatment, usually 0.1 to 10,000 ppm per active ingredient, Desirably, it is 1 to 2,000 ppm. In the case of soil treatment, it is usually 10 to 100,000 g / ha, preferably 200 to 20,000 g / ha. In the case of seed treatment, it is usually 0.01 to 100 g / Kg seed, preferably 0.02 to 20 g / Kg seed.

  The compound of the present invention is generally applied for application of its various preparations or dilutions thereof, that is, spraying (for example, spraying, spraying, misting, atomizing, dusting, water surface application, etc.), soil It can be performed by application (mixing, irrigation, etc.), surface application (application, powder coating, coating, etc.) and the like. It can also be applied by the so-called ultra low volume application method. In this method, it is possible to contain 100% of the active ingredient.

  The compound of the present invention may contain other agricultural chemicals as necessary, such as fungicides, insecticides, acaricides, nematicides, soil insecticides, antiviral agents, attractants, herbicides, plant growth preparations, etc. Can be mixed and used together. In this case, a more excellent effect may be exhibited.

In the above-mentioned other agricultural chemicals, as an active ingredient compound of a bactericide (generic name; including some pending applications or Japan Plant Protection Association test code), for example,
Anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil;
Tria like 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine Zolopyrimidine compounds;
Pyridinamine compounds such as fluazinam;
Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole cyproconazole, tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, o Oxpoconazole fumarate, prothioconazole, triadimenol, flutriafol, difenoconazole, fluquinconazole azole), fenbuconazole, bromuconazole, diniconazole, tricyclazole, probenazole, simeconazole, pefazoate, ipconazole, imibenconazole Azole compounds such as (imibenconazole), azaconazole, triticonazole, imazalil;
Quinoxaline compounds such as quinomethionate;
Dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, thiram;
Organochlorine compounds such as fthalide, chlorothalonil, quintozene;
Imidazole compounds such as benomyl, thiophanate-methyl, carbendazim, thiabendazole, fuberiazole, cyazofamid;
Cyanoacetamide compounds such as cymoxanil;
Metalaxyl, metalaxyl-M (also known as mefenoxam), oxadixyl, offurace, benalaxyl, benalaxyl-M, also known as kiralaylyl )), Flaxaxyl, cyprofuram, carboxin, oxycarboxin, thifluzamide, boscalid, bixafen, isothianil, tiadinil Anilide compounds such as sedaxane;
Sulfamide-type compounds such as dichlofluanid;
Copper-based compounds such as cupric hydroxide and oxine copper;
Isoxazole compounds such as hymexazol;
Fosetyl aluminum (fosetyl-Al), tolclofos-Methyl, S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, aluminum ethyl hydrogen phosphonate, edifenphos, iprobenphos Organophosphorus compounds such as (iprobenfos);
Phthalimide compounds such as captan, captafol, folpet;
Dicarboximide compounds such as procymidone, iprodione, vinclozolin;
Benzanilide compounds such as flutolanil, mepronil, benodanil;
Penthiopyrad, penflufen, furametpyr, isopyrazam, silthiopham, fenoxanil, fenfuram, flufurapiroxad, benzovindiflupyr Amide compounds such as
Benzamide compounds such as fluopyram and zoxamide;
Piperazine compounds such as triforine;
Pyridine compounds such as pyrifenox and pyrisoxazole;
Carbinol compounds such as fenarimol and nuarimol;
Piperidine compounds such as fenpropidin;
Morpholine compounds such as fenpropimorph and tridemorph;
Organotin compounds such as fentin hydroxide and fentin acetate;
Urea-based compounds such as pencycuron;
Synamic acid compounds such as dimethomorph, flumorph;
Phenyl carbamate compounds such as dietofencarb;
Cyanopyrrole compounds such as fludioxonil and fenpiclonil;
Azoxystrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin ( dimoxystrobin), pyraclostrobin, fluoxastrobin, enestroburin, pyroxystrobin, pyrametostrobin, coumoxystrobin, enoxast Strobilurin-based compounds such as enoxastrobin, fenaminstrobin, flufenoxystrobin, triclopyricarb;
Oxazolidinone compounds such as famoxadone;
Thiazole carboxamide compounds such as ethaboxam;
Valinamide compounds such as iprovalicarb, benchthiavalicarb-isopropyl;
Acylamino acid compounds such as methyl N- (isopropoxycarbonyl) -L-valyl- (3RS) -3- (4-chlorophenyl) -β-valaniphenate;
Imidazolinone compounds such as fenamidone;
Hydroxyanilide compounds such as fenhexamid;
Benzenesulfonamide compounds such as flusulfamide;
Oxime ether compounds such as cyflufenamid;
Anthraquinone compounds;
Crotonic acid compounds;
Antibiotics such as validamycin, kasugamycin, polyoxins;
Guanidine compounds such as iminoctadine and dodine;
Quinoline compounds such as tebufloquin;
Thiazolidine compounds such as flutianil;
Sulfur-based compounds such as sulfur;
Other compounds include pyribencarb, isoprothiolane, pyroquilon, diclomezine, quinoxyfen, propamocarb hydrochloride, chloropicrin, dazomet, metam Sodium salt (metam-sodium), metrafenone, nicobifen, UBF-307, diclocymet, proquinazid, amisulbrom (aka amibromdole), mandipropamid, fluopide fluopicolide, carpropamid, meptyldinocap, isofetamid, pyriofenone, ferimzone, spiroxamine (spiro) xamine), fenpyrazamine, ametoctradin, valifenalate, oxathiapiprolin, tolprocarb, NK-1001, SB-4303, MIF-1001, MIF-1002, BAF -1107, NF-171, SYJ-247, NNF-0721 and the like.

Insecticides, acaricides, nematicides or soil pesticides in the above-mentioned other pesticides, that is, active ingredient compounds of pesticides (generic name; including some pending applications or Japan Plant Protection Association test code) ), For example,
Profenofos, dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiophos, prothiophos Fosthiazate, cadusafos, disulfoton, isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate ), Sulprofos, thiometon, bamidothion, pyraclofos, pyridaphenthion, pirimiphos-methyl, pirimiphos-methyl Propaphos, phosalone, formothion, malathion, tetrachlorvinphos, chlorfenvinphos, cyanophos, trichlorfon, methidathion , Phenthoate, ESP, azinphos-methyl, fenthion, heptenophos, methoxychlor, parathion, phosphocarb, demeton-S-S- such as methyl, monocrotophos, methamidophos, imicyafos, parathion-methyl, terbufos, phosphamidon, phosmet, phorate Machine phosphoric ester compound;
Carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, fenobucarb Carbamates such as carbosulfan, benfuracarb, bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb, XMC, fenothiocarb Compound;
Nereistoxin derivatives such as cartap, thiocyclam, bensultap, sodium thiosultap-sodium;
Organochlorine compounds such as dicophor, tetradifon, endosulfan, dienochlor, dieldrin;
Organometallic compounds such as fenbutatin oxide and cyhexatin;
Fenvalerate, permethrin, cypermethrin, deltamethrin, cyhalothrin, tefluthrin, etofenprox, flufenprox, cyfluthrin , Fenpropathrin, flucythrinate, fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrin, esfenvalerate, tetramethrin (Tetramethrin), resmethrin, protrifenbute, bifenthrin, zeta-cypermethrin, acrinathrin, alpha-cypermethrin alpha-cypermethrin, allethrin, gamma-cyhalothrin, theta-cypermethrin, tau-fluvalinate, tralomethrin, profluthrin, beta -Pyrethroid compounds such as cypermethrin, beta-cyfluthrin, methfluthrin, phenothrin, flumethrin;
Diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron, novaluron, triflumuron, hexaflumuron, hexaflumuron Benzoylurea compounds such as (bistrifluron), nobifluuron, fluazuron;
Juvenile hormone-like compounds such as metoprene, pyriproxyfen, fenoxycarb, diofenolan;
Pyridazinone compounds such as pyridaben;
Pyrazole compounds such as fenpyroximate, fipronil, tebufenpyrad, ethiprole, tolfenpyrad, acetoprole, pyrafluprole, pyriprole;
Imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, nidinotefuran, dinotefuranit, dinotefuranit A noid compound;
Hydrazine compounds such as tebufenozide, methoxyfenozide, chromafenozide, halofenozide;
Pyridine compounds such as pyridalyl and flonicamid;
Cyclic ketoenol compounds such as spirodiclofen, spiromesifen, spirotetramat;
Strobilurin-based compounds such as fluacrypyrim;
Pyrimidinamine compounds such as flufenerim;
Dinitro compounds;
Organic sulfur compounds;
Urea compounds;
Triazine compounds;
Hydrazone compounds;
Other compounds include buprofezin, hexythiazox, amitraz, chlordimeform, silafluofen, triazamate, pymetrozine, pyrimidifen, chloridmefen ), Indoxacarb, acequinocyl, etoxazole, cyromazine, 1,3-dichloropropene, diafenthiuron, benclothiaz , Bifenazate, propargite, clofentezine, metaflumizone, flubendiamide, cyflumetofen, chlorantani Chlorantraniliprole, cyantraniliprole, cyenopyrafen, pyrifluquinazone, phenazaquin, amiazaflumet, sulfluramid, hydramethylnon, aldehyde , Compounds such as sulfoxaflor, cypropene, fluensulfone, ryanodine, verbutin; and the like. Furthermore, Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis or crystalline protein toxins produced by Bacillus thuringiensis, entomopathogenic fungi, nematode pathogenic fungi, etc. Microbial pesticides such as: avermectin, emamectin benzoate, milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE-175, abamectin ), Antibiotics such as emamectin, spinetoram and semi-synthetic antibiotics; natural products such as azadirachtin and rotenone; repellents such as deet; Mixed with , Can be used together.

  Next, examples of the present invention will be described, but the present invention is not limited thereto. First, the synthesis example of this invention compound is described.

Synthesis example 1
Synthesis of N- (2,2-difluoro-2- (4-((5- (trifluoromethyl) pyridin-2-yl) oxy) phenyl) ethyl) quinazolin-4-amine (Compound No. 1)

Step 1. 2- (4-Iodophenoxy) -5- (trifluoromethyl) pyridine

To a mixed solution of 4-iodophenol (25.36 g), 2-chloro-5- (trifluoromethyl) pyridine (25.17 g), and N, N-dimethylformamide (250 mL), potassium carbonate (19.17 g) was added, Stir at 80 ° C. for 18 hours. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted twice with ethyl acetate. The combined organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate / heptane = 1/20) to give 2- (4-iodophenoxy) -5- (trifluoromethyl) pyridine (34.96 g). It was.
_{^{1 H NMR (CDCl 3 /500MHz):δ(ppm)=8.43(1H,}} d), 7.92 (1H, dd), 7.73 (2H, d), 7.04 (1H, d), 6.93 (2H, d)

Step 2. Ethyl 2,2-difluoro-2- (4-((5- (trifluoromethyl) pyridin-2-yl) oxy) phenyl) acetate

Copper powder (4.36 g) was added to the reaction vessel to form a nitrogen atmosphere, and then a solution of ethyl bromodifluoroacetate (8.61 g) in dimethyl sulfoxide (50 mL) was added dropwise and stirred at room temperature for 30 minutes. Subsequently, a solution of 2- (4-iodophenoxy) -5- (trifluoromethyl) pyridine (10.01 g) in dimethyl sulfoxide (50 mL) was added dropwise and stirred at 40 ° C. for 18 hours. The reaction mixture was cooled to room temperature, saturated aqueous ammonium chloride solution and ethyl acetate were added, and the insoluble material was filtered off.
The filtrate was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with saturated aqueous ammonium chloride solution and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate / heptane = 1/10) to obtain ethyl 2,2-difluoro-2- (4-((5- (trifluoromethyl) pyridine- 2-yl) oxy) phenyl) acetate (8.04 g) was obtained.
_{^{1 H NMR (CDCl 3 / 500MHz}} ): δ (ppm) = 8.45 (1H, d), 7.95 (1H, d), 7.69 (2H, d), 7.25 (2H, d), 7.08 (1H, d), 4.32 (2H, q), 1.34 (3H, t)

Step 3. 2,2-Difluoro-2- (4-((5- (trifluoromethyl) pyridin-2-yl) oxy) phenyl) ethanol

To a mixed solution of ethyl 2,2-difluoro-2- (4-((5- (trifluoromethyl) pyridin-2-yl) oxy) phenyl) acetate (26.72 g) and ethanol (400 mL) at 0 ° C. , Sodium borohydride (4.21 g) was added, and the mixture was stirred at the same temperature for 1 hour. Then, it heated up to room temperature and stirred for 18 hours. 1N Hydrochloric acid was added to stop the reaction, and ethanol was evaporated under reduced pressure. Subsequently, water was added and extracted twice with ethyl acetate. The combined organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate / heptane = 1/3) to give 2,2-difluoro-2- (4-((5- (trifluoromethyl) pyridine-2. -Yl) oxy) phenyl) ethanol (21.55 g) was obtained.
_{^{1 H NMR (CDCl 3 /500MHz):δ(ppm)=8.44(1H,}} d), 7.94 (1H, dd), 7.60 (2H, d), 7.24 (2H, d), 7.07 (1H, d), 4.00 (2H, dt), 2.01 (1H, t)

Step 4. 2- (4- (1,1-Difluoro-2-iodoethyl) phenoxy) -5- (trifluoromethyl) pyridine

2,2-difluoro-2- (4-((5- (trifluoromethyl) pyridin-2-yl) oxy) phenyl) ethanol (19.62 g), triphenylphosphine (24.20 g), imidazole (8.40 g), To a mixed solution of toluene (120 mL) and acetonitrile (60 mL) was added iodine (23.41 g) at 0 ° C., and the mixture was stirred at the same temperature for 1 hour. Then, it heated up at 90 degreeC and stirred for 12 hours. After cooling the reaction mixture to room temperature, the insoluble material was filtered off and washed with toluene. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate / heptane = 1/15) to give 2- (4- (1,1-difluoro-2-iodoethyl) Phenoxy) -5- (trifluoromethyl) pyridine (20.41 g) was obtained.
_{^{1 H NMR (CDCl 3 /500MHz):δ(ppm)=8.45(1H,}} d), 7.94 (1H, t), 7.57 (2H, d), 7.24 (2H, d), 7.08 (1H, d), 3.68 (2H, t)

Step 5. 2- (2,2-Difluoro-2- (4-((5- (trifluoromethyl) pyridin-2-yl) oxy) phenyl) ethyl) isoindoline-1,3-dione

To a mixed solution of 2- (4- (1,1-difluoro-2-iodoethyl) phenoxy) -5- (trifluoromethyl) pyridine (23.44 g) and N, N-dimethylformamide (300 mL), phthalimide potassium salt And stirred at 120 ° C. for 15 hours. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted twice with ethyl acetate. The combined organic layers were washed with 1N aqueous potassium hydroxide solution and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate / heptane = 1/3) to give 2- (2,2-difluoro-2- (4-((5- (trifluoromethyl)). Pyridin-2-yl) oxy) phenyl) ethyl) isoindoline-1,3-dione (12.01 g) was obtained.
_{^{1 H NMR (CDCl 3 /500MHz):δ(ppm)=8.45(1H,}} d), 7.94 (1H, dd), 7.91 (2H, dd), 7.77 (2H, dd), 7.67 (2H, d), 7.25 (2H, d), 7.06 (1H, d), 4.29 (2H, t)

Step 6. 2,2-Difluoro-2- (4-((5- (trifluoromethyl) pyridin-2-yl) oxy) phenyl) ethanamine

2- (2,2-difluoro-2- (4-((5- (trifluoromethyl) pyridin-2-yl) oxy) phenyl) ethyl) isoindoline-1,3-dione (6.70 g), and ethanol To a mixed solution of (150 mL), 80% hydrazine monohydrate (2.41 g) was added dropwise and stirred at 60 ° C. for 5 hours. The reaction mixture was cooled to room temperature, insoluble matters were filtered off, and the filtrate was concentrated under reduced pressure. Ethyl acetate was added to the resulting residue, the precipitated crystals were again filtered off, and the filtrate was washed with 1N aqueous sodium hydroxide solution and saturated brine. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and 2,2-difluoro-2- (4-((5- (trifluoromethyl) pyridin-2-yl) oxy) phenyl) Ethanamine (4.66 g) was obtained.
_{^{1 H NMR (CDCl 3 /500MHz):δ(ppm)=8.44(1H,}} d), 7.94 (1H, dd), 7.55 (2H, d), 7.23 (2H, d), 7.07 (1H, d), 3.20 (2H, m), 1.51 (2H, br)

Step 7. N- (2,2-difluoro-2- (4-((5- (trifluoromethyl) pyridin-2-yl) oxy) phenyl) ethyl) quinazolin-4-amine (Compound No. 1)

2,2-difluoro-2- (4-((5- (trifluoromethyl) pyridin-2-yl) oxy) phenyl) ethanamine (4.66 g), 4-chloroquinazoline (3.37 g), and N, N- Triethylamine (4.15 g) was added to a mixed solution of dimethylformamide (250 mL), and the mixture was stirred at 80 ° C. for 18 hours. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted twice with ethyl acetate. The combined organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (eluent: ethyl acetate / heptane = 1/2), recrystallized with ethyl acetate and heptane, and N- (2,2-difluoro-2- ( 4-((5- (trifluoromethyl) pyridin-2-yl) oxy) phenyl) ethyl) quinazolin-4-amine (3.43 g) was obtained.
_{^{1 H NMR (CDCl 3 /500MHz):δ(ppm)=8.66(1H,}} s), 8.44 (1H, s), 7.94 (1H, d), 7.89 (1H, d), 7.78 (2H, dd), 7.67 (2H, d), 7.54 (1H, dd), 7.23 (2H, d), 7.04 (1H, d), 5.99 (1H, br), 4.48 (2H, dt)

In Table 1, the numerical values shown as physical properties are melting points (° C.). These compounds can be synthesized based on the above synthesis examples or the above-described production method of the compound of the present invention. In Table 1, Me represents methyl and Et represents ethyl. A circle part (◯) of the substituent A indicates that an A-NH bond is formed at the part. The circle part (◯) of the substituent B also indicates that the part forms an OB bond. The substitution position on the benzene ring of R ¹ follows that numbered in the chemical structural formula in the table. The value of m refers to the representation of R ^1. A compound without R ¹ (m = 0) is indicated as “−”.

Table 2 shows ¹ H-NMR data [measured by ¹ H-nuclear magnetic resonance spectroscopy; δ is a chemical shift value (ppm)] for some of the compounds of the present invention.

Below, the test example of this invention composition is described. In each test, the control index followed the following criteria.
[Control index of various preventive effect tests] [Disease level: Visual observation]
5: No lesion or sporulation is observed.
4: The lesion area, the number of lesions, or the spore formation area is less than 10% of the untreated area.
3: The lesion area, the number of lesions, or the sporulation area is less than 40% of the untreated area.
2: The lesion area, the number of lesions, or the sporulation area is less than 70% of the untreated area.
1: The lesion area, the number of lesions, or the spore formation area is 70% or more of the untreated area.

Test example 1 (wheat powdery mildew prevention effect test)
Growing wheat (variety: Norin 61) in a plastic pot with a diameter of 6.0 cm, and when the 1.5 leaf stage is reached, a mixed drug solution in which each test compound is adjusted to a predetermined concentration is sprayed per seedling. 10 ml was sprayed. After the drug solution was dried, it was inoculated with conidia spores of wheat powdery mildew (Erysiphe graminis) and kept in a constant temperature room at 20 ° C. Seven days after the inoculation, the number of lesions was investigated, and a control index was determined according to the above evaluation criteria.
Compound No. When tested for 2, 4, 5, 6 and 55, an effect of controlling index 4 or more was shown at 400 ppm.

Test example 2 (wheat blight prevention effect test)
Wheat (variety: Norin 61) was cultivated in a plastic pot with a diameter of 6.0 cm, and when the 1.5 leaf stage was reached, a sufficient amount of chemical solution adjusted to a predetermined concentration of the compound of the present invention was sprayed with a spray gun. . After the chemical solution is dried (on the day of treatment), spray inoculate with a conidial spore suspension of Septoria nodorum, keep it in an inoculation box at 20 ° C for about 1 day, and then keep it in a constant temperature room at 20 ° C. It was. The number of lesions was investigated 10-13 days after the inoculation, and the control index was determined according to the above evaluation criteria.
Compound No. When tested for 2, 5 and 55, it showed an effect of a control index of 4 or more at 400 ppm.

Test example 3 (wheat red rust prevention effect test)
Growing wheat (variety: Norin 61) in a plastic pot with a diameter of 6.0 cm, and using a spray gun, mixed seedlings with each test compound adjusted to a predetermined concentration when the 1.5 leaf stage was reached. 10ml was sprayed. After the drug solution was dried, the conidia of Puccinia recondita were sprinkled and inoculated, kept in an inoculation box at 20 ° C. for about 1 day, and then kept in a constant temperature room at 20 ° C. Seven days after the inoculation, the number of lesions was investigated, and a control index was determined according to the above evaluation criteria.
Compound No. When 1, 2, 3, 4, 5, 6 and 55 were tested, the effect of controlling index 4 or more was shown at 400 ppm.

Test Example 4 (Tomato plague prevention effect test)
A tomato (variety: yellow pair) was cultivated in a 7.5 cm diameter plastic pot, and when the three-leaf stage was reached, a sufficient amount of a chemical solution prepared by adjusting the compound of the present invention to a predetermined concentration was sprayed with a spray gun. After the chemical solution was dried (on the day of treatment or the next day), a zoosporangium suspension of Phytophthora infestans was spray-inoculated and kept in a constant temperature room at 20 ° C. Three days after the inoculation, the lesion area was examined, and the control index was determined according to the evaluation criteria.
Compound No. When tested for 1, 2, 4, 5, 6 and 55, an effect of controlling index 4 or more was shown at 400 ppm.

Test Example 5 (Cucumber downy mildew prevention effect test)
Cucumber (variety: Sagamihanjiro) was cultivated in a plastic pot with a diameter of 7.5 cm, and when the 1.5 leaf stage was reached, a sufficient amount of chemical solution adjusted to a predetermined concentration of the compound of the present invention was sprayed with a spray gun. . After the drug solution was dried (on the day of treatment), a zoosporangium suspension of Pseudoperonospora cubensis was spray-inoculated and kept in a 20 ° C. inoculation box for about 1 day and kept in a constant temperature room at 20 ° C. . Seven days after the inoculation, the lesion area was examined, and the control index was determined according to the evaluation criteria.
Compound No. When 1, 2, 3, 4, 5, 6 and 55 were tested, the effect of controlling index 4 or more was shown at 400 ppm.

Test Example 6 (Cucumber powdery mildew prevention effect test)
Cucumber (variety: Sagamihanjiro) was cultivated in a plastic pot with a diameter of 7.5 cm, and when the 1.5 leaf stage was reached, a sufficient amount of chemical solution adjusted to a predetermined concentration of the compound of the present invention was sprayed with a spray gun. . After the chemical solution was dried (on the day of treatment), a spore suspension of Sphaerotheca fuliginea was spray-inoculated and kept in a constant temperature room at 20 ° C. Seven days after the inoculation, the lesion area was examined, and the control index was determined according to the evaluation criteria.
Compound No. When 1, 2, 3, 4, 5, 6 and 55 were tested, the effect of controlling index 4 or more was shown at 400 ppm.

Formulation Example 1
(1) Compound of the present invention 20 parts by weight (2) 72 parts by weight of clay (3) Sodium lignin sulfonate 8 parts by weight The above is uniformly mixed to obtain a wettable powder.

Formulation Example 2
(1) Compound of the present invention 5 parts by weight (2) 95 parts by weight of talc The above components are uniformly mixed to form a powder.

Formulation Example 3
(1) 20 parts by weight of the present compound (2) 20 parts by weight of N, N-dimethylacetamide (3) 10 parts by weight of polyoxyethylene alkylphenyl ether (4) 50 parts by weight of xylene To make an emulsion.

Formulation Example 4
(1) Clay 68 parts by weight (2) Lignin sulfonic acid soda 2 parts by weight (3) Polyoxyethylene alkylaryl ether sulfate 5 parts by weight (4) Fine silica 25 parts by weight Are mixed at a weight ratio of 4: 1 to obtain a wettable powder.

Formulation Example 5
(1) Compound of the present invention 50 parts by weight (2) Oxidated polyalkylphenyl phosphate triethanolamine
2 parts by weight (3) 0.2 parts by weight of silicone (4) 47.8 parts by weight of water Further mixed into the stock solution obtained by uniformly mixing and grinding the above (5) 5 parts by weight of sodium polycarboxylate (6) anhydrous sodium sulfate Add 42.8 parts by weight, mix uniformly, granulate, and dry to make granule wettable powder.

Formulation Example 6
(1) Compound of the present invention 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene phosphate ester 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight (1) to (3) is uniformly mixed in advance and diluted with an appropriate amount of acetone, and then sprayed onto (4) to remove the acetone and form granules.

Formulation Example 7
(1) Compound of the present invention 2.5 parts by weight (2) N-methyl-2-pyrrolidone 2.5 parts by weight (3) Soybean oil 95.0 parts by weight (Ultra low volume formulation).

Formulation Example 8
(1) 20 parts by weight of the present compound (2) Oxidated polyalkylphenyl phosphate triethanolamine
2 parts by weight (3) 0.2 parts by weight of silicone (4) 0.1 parts by weight of xanthan gum (5) 5 parts by weight of ethylene glycol (6) 72.7 parts by weight of water Use a suspension.

  Since the compound of the present invention has a high control effect against a wide range of plant pathogenic bacteria and also has high safety, it is useful as an agricultural and horticultural fungicide.

Claims (4)

Formula (I):

[Where:
A is pyrimidine or quinazoline, optionally substituted with X;
X is selected from the group consisting of halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, cycloalkyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio and haloalkylthio;
B is pyridine optionally substituted with Y;
Y is selected from the group consisting of halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio and haloalkylthio;
R ¹ is selected from the group consisting of halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylthio and haloalkylthio;
m is an integer of 0 to 4]
Or a salt thereof. The compound or a salt thereof according to claim 1, wherein A binds to -NH- at the 4-position of pyrimidine or quinazoline. An agricultural and horticultural fungicide containing the compound according to claim 1 or a salt thereof as an active ingredient. A method for controlling plant diseases, which comprises applying the compound according to claim 1 or a salt thereof to plants or soil.