JP5173126B2 - Bactericidal composition containing acid amide derivative - Google Patents

Description

  The present invention relates to a bactericidal composition containing an acid amide derivative.

  WO2001 / 60783 and WO2003 / 27059 describe that an acid amide derivative having a certain chemical structure is useful as an active ingredient of a pest control agent. However, it does not describe that the compound of the formula (I) described later has a bactericidal action. On the other hand, the applicant's Japanese Patent Application No. 2003-420864 describes a bactericidal composition containing an acid amide derivative as an active ingredient, but the active ingredient compound is different from the compound of formula (I) described later. .

International Publication WO 01/60783 International Publication WO 03/27059 Japanese patent application Japanese Patent Application No. 2003-420864

  Many of the bactericidal compositions that have been provided so far have insufficient preventive or therapeutic effects, insufficient residual effects, or depending on the application situation against plant diseases. It has some practical problems such as insufficient control effect. Accordingly, there is a need for a bactericidal composition that overcomes these problems.

As a result of studies to solve the above-mentioned problems, the present inventors have found that a bactericidal composition containing an acid amide derivative represented by the following formula (I) has various harmful fungi such as oomycetes, ascomycetes, basidiomycetes. It has been found that it exhibits excellent preventive and therapeutic effects against various diseases caused by fungi and incomplete fungi, and at the same time has practically satisfactory residual effects, thereby completing the present invention.
That is, the present invention relates to the formula (I):

Wherein A is phenyl optionally substituted with X, benzyl optionally substituted with X, naphthyl optionally substituted with X, heterocycle optionally substituted with X, optionally substituted with X A fused heterocycle, indanyl (indanyl may be substituted with halogen, alkyl or alkoxy) or tetrahydronaphthyl (tetrahydronaphthyl may be substituted with halogen, alkyl or alkoxy); B is substituted with Y An optionally substituted heterocycle (excluding pyridyl), a fused heterocycle optionally substituted with Y, or a naphthyl optionally substituted with Y; X is halogen, alkyl optionally substituted with E ¹ , E alkenyl which may be substituted with ^1, an alkynyl be substituted by E ^1, hydroxy, Shianookishi, which may be substituted by E ¹ alkoxy, optionally substituted by E ¹ There alkenyloxy, good alkynyloxy optionally substituted by E ^1, mercapto, Shianochio, alkylthio substituted by E ^1, which may be substituted by E ¹ alkenylthio which may be substituted by E ¹ alkynylthio , optionally substituted alkylsulfinyl at E ^2, optionally alkylsulfonyl substituted with E ^2, cycloalkyl which may be substituted by J, which may be substituted by J cycloalkyloxy, optionally substituted with J Good cycloalkylthio, cyano, nitro, formyl, phenyl optionally substituted with Y, phenoxy optionally substituted with Y, phenylthio optionally substituted with Y, phenylalkyl optionally substituted with Y, substituted with Y Phenylalkenyl which may be substituted, phenylalkynyl which may be substituted with Y, phenylayl which may be substituted with Y Kiloxy, phenylalkenyloxy optionally substituted with Y, phenylalkynyloxy optionally substituted with Y, phenylalkylthio optionally substituted with Y, phenylalkenylthio optionally substituted with Y, substituted with Y Phenylalkynylthio which may be substituted, phenylamino which may be substituted with Y, —OR ⁴ , —SR ⁵ , —NR ⁶ R ⁷ , —CO ₂ R ⁸ , —C (═O) NR ⁸ R ⁹ , —SO ₂ NR ⁸ R ⁹ , —CH═NR ¹⁰ or a heterocycle (the heterocycle may be substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylcarbonyl); Y is substituted with halogen, E ¹ may be alkyl, alkenyl which may be substituted by E ^1, an alkynyl be substituted by E ^1, hydroxy, Shianookishi, which may be substituted by E ¹ alkoxy , Good alkenyloxy optionally substituted by E ^1, good alkynyloxy optionally substituted by E ^1, mercapto, Shianochio, alkylthio substituted by E ^1, which may be substituted by E ¹ alkenylthio, E ¹ in optionally substituted alkynylthio, optionally substituted alkylsulfinyl at E ^2, optionally alkylsulfonyl substituted with E ^2, cycloalkyl which may be substituted by J, cycloalkyl which may be substituted with J Oxy, cycloalkylthio optionally substituted with J, cyano, nitro, formyl, —OR ⁴ , —SR ⁵ , —NR ⁶ R ⁷ , —CO ₂ R ⁸ , —C (═O) NR ⁸ R ⁹ , — _{^{SO 2 NR 8 R 9, -CH}} = NR 10 or the heterocyclic (heterocycle, halogen, alkyl, haloalkyl, alkoxy, may be substituted with a haloalkoxy, or alkylcarbonyl) der ; R ¹ and R ² each independently represent a hydrogen atom, alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl, cyanoalkyl, alkoxycarbonylalkyl, alkenyl, haloalkenyl, alkoxyalkenyl, alkynyl, haloalkynyl, alkoxy alkynyl, Cycloalkyl, halocycloalkyl, (alkyl) cycloalkyl, (haloalkyl) cycloalkyl, cyano or —CO ₂ R ⁸ , and R ¹ and R ² together form a 3-6 membered saturated carbocycle. at best; R ³ is a hydrogen atom, alkyl which may be substituted by E ^1, alkenyl which may be substituted by E ^1, which may be alkynyl substituted by E ^1, hydroxy, Shianookishi, substituted with E ¹ May be alkoxy, cycloalkyl optionally substituted with J, Which may be cycloalkyloxy, optionally cycloalkylthio optionally substituted by a J, cyano, ^{formyl, -C (= W 3) R} 11, -C (= W 3) OR 12, -C (= W 3) SR ¹² , —C (═W ³ ) NR ¹² R ¹³ , —S (O) mR ¹² or —S (O) nNR ¹² R ¹³ ; R ⁴ is —C (= W ³ ) R ¹² , —C ( ^{= W 3) oR 12, -C} (= W 3) SR 12, -C (= W 3) NR 12 R 13, -S (O) mR 12, -S (O) nNR 12 R 13 , or heterocycle ( The heterocycle is optionally substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylcarbonyl; R ⁵ is —C (═W ³ ) R ¹² , —C (═W ³ ) OR ¹² , —C (═W ³ ) SR ¹² , —C (═W ³ ) NR ¹² R ¹³ or a heterocycle (the heterocycle may be substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylcarbonyl). Yes R ⁶ is a hydrogen atom, an alkyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, cyanoalkyl, (cycloalkyl) alkyl, cycloalkyl, ^{cyano, -C (= W 3) R} 12, -C (= W 3) OR 12 ^{, -C (= W 3) SR} 12, -C (= W 3) NR 12 R 13, -S (O) mR 12, -S (O) nNR 12 R 13 or a heterocyclic ring (heterocycle, halogen, R ⁷ is a hydrogen atom, alkyl, haloalkyl, alkoxyalkyl, or haloalkoxyalkyl; R ⁸ and R ⁹ are each independently hydrogen, and may be substituted with alkyl, haloalkyl, alkoxy, haloalkoxy, or alkylcarbonyl. atom, alkyl, haloalkyl, alkoxyalkyl or haloalkoxyalkyl, adjacent R ⁸ and R ⁹ may form a ring together; R ¹⁰ is alkyl (alkyl Optionally substituted by halogen, alkoxy or haloalkoxy), alkoxy (alkoxy may be substituted by halogen, alkoxy or haloalkoxy), alkenyloxy (alkenyloxy is substituted by halogen, alkoxy or haloalkoxy) 11), alkynyloxy (alkynyloxy may be substituted with halogen, alkoxy or haloalkoxy) or alkoxycarbonyl (alkoxycarbonyl may be substituted with halogen, alkoxy or haloalkoxy); R ¹¹ Is a hydrogen atom, alkyl optionally substituted with E ³ , phenyl (phenyl may be substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylcarbonyl) or heterocycle (heterocycle is halogen, alkyl, R ¹² and R ¹³ are each independently substituted with alkyl, alkoxy, haloalkoxy, J, optionally substituted with E ^3. Cycloalkyl or phenyl (phenyl may be substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylcarbonyl), and adjacent R ¹² and R ¹³ together form a ring W ¹ , W ² and W ³ are each independently an oxygen atom or a sulfur atom; m and n are each independently an integer of 0 to 2; E ¹ is halogen, hydroxy, alkoxy, haloalkoxy, Mercapto, alkylthio, haloalkylthio, alkylsulfonyl, cycloalkyl, amino, monoalkylamino, dial A ruamino, cyano, nitro, hydroxycarbonyl, alkoxycarbonyl, alkylcarbonyloxy, trialkylsilyl or heterocycle (the heterocycle may be substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylcarbonyl); E ² is halogen, hydroxy, alkoxy, haloalkoxy, cycloalkyl, amino, monoalkylamino, dialkylamino, cyano, nitro, hydroxycarbonyl, alkoxycarbonyl, trialkylsilyl or heterocycle (the heterocycle is halogen, alkyl, haloalkyl) , alkoxy, haloalkoxy or may be substituted with alkylcarbonyl); E ³ is halogen, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino, consequent Alkyl, cyano, alkoxycarbonyl, haloalkoxy, haloalkylthio or phenyl (phenyl may be substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylcarbonyl); J is halogen, alkyl, haloalkyl, alkoxy Or a haloalkoxy] or a salt thereof as an active ingredient. Further, the present invention provides a method for controlling various diseases caused by various harmful fungi or various harmful fungi by applying an effective amount of the derivative or a salt thereof, and applying an effective amount of the derivative or a salt thereof. The present invention relates to a method for protecting crops or improving crop yields. Furthermore, the present invention provides a compound of formula (I-α) that has not been specifically known conventionally:

[A ^alpha phenyl which may be substituted with X ^alpha, naphthyl substituted by X ^alpha, X thienyl substituted with ^alpha, be substituted with X ^alpha good benzodioxolanyl or be substituted with X ^alpha B is a heterocyclic ring optionally substituted with Y (excluding pyridyl), a condensed heterocyclic ring optionally substituted with Y, or naphthyl optionally substituted with Y; X ^α is fluorine atom, chlorine atom, iodine atom, alkyl, haloalkyl, alkoxyalkyl, dialkylaminoalkyl, alkynyl, trialkylsilylalkynyl, hydroxy, alkoxy, haloalkoxy, alkoxyalkoxy, cycloalkyl, nitro, phenyl, phenylalkynyl, haloalkyl Pyridyloxy, alkylcarbonyloxy, alkylsulfonyl optionally substituted by Alkoxy or a heterocyclic ring (heterocycle, halogen, alkyl or substituted alkylcarbonyl may also be) be; Y is halogen, alkyl which may be substituted by E ^1, alkenyl which may be substituted by E ^1, E which may be alkynyl substituted with ^1, hydroxy, Shianookishi, alkoxy substituted by E ^1, good alkenyloxy optionally substituted by E ^1, good alkynyloxy optionally substituted with E ^1, mercapto, Shianochio, E alkylthio substituted with ^1, may be substituted by E ¹ alkenylthio which may be substituted by E ¹ alkynylthio, optionally substituted alkylsulfamoyl be nyl at E ^2, may be substituted with E ² Alkylsulfonyl, cycloalkyl optionally substituted with J, cycloalkyloxy optionally substituted with J, cycle optionally substituted with J Alkylthio, cyano, nitro, ^{formyl, -OR 4, -SR 5, -NR} 6 R 7, -CO 2 R 8, -C (= O) NR 8 R 9, -SO 2 NR 8 R 9, -CH = NR ¹⁰ or a heterocycle (the heterocycle may be substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylcarbonyl); R ¹ and R ² are each independently a hydrogen atom, alkyl, haloalkyl, hydroxy Alkyl, alkoxyalkyl, haloalkoxyalkyl, cyanoalkyl, alkoxycarbonylalkyl, alkenyl, haloalkenyl, alkoxyalkenyl, alkynyl, haloalkynyl, alkoxyalkynyl, cycloalkyl, halocycloalkyl, (alkyl) cycloalkyl, (haloalkyl) cycloalkyl , cyano or -CO ₂ R ^8, and R ¹ and R ² May form a 3-6 membered saturated carbon ring together; R ³ is a hydrogen atom, alkyl which may be substituted by E ^1, alkenyl which may be substituted by E ^1, it is substituted by E ¹ Alkynyl, hydroxy, cyanooxy, alkoxy optionally substituted with E ¹ , cycloalkyl optionally substituted with J, cycloalkyloxy optionally substituted with J, cycloalkylthio optionally substituted with J, cyano , ^{formyl, -C (= W 3) R} 11, -C (= W 3) OR 12, -C (= W 3) SR 12, -C (= W 3) NR 12 R 13, -S (O) mR be ¹² or ^{-S (O) nNR 12 R 13} ; R 4 is ^{-C (= W 3) R 12} , -C (= W 3) oR 12, -C (= W 3) SR 12, -C ^{(= W 3) NR 12 R} 13, -S (O) mR 12, -S (O) nNR 12 R 13 or a heterocyclic ring (heterocycle, halogen, alkyl, haloalkyl, alkoxy, Haroaruko Substituted with or alkylcarbonyl be also be); R ⁵ is ^{-C (= W 3) R 12} , -C (= W 3) OR 12, -C (= W 3) SR 12, -C ( = W ³ ) NR ¹² R ¹³ or a heterocycle (the heterocycle may be substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylcarbonyl); R ⁶ is a hydrogen atom, alkyl, haloalkyl, alkoxy alkyl, halo alkoxyalkyl, cyanoalkyl, (cycloalkyl) alkyl, cycloalkyl, ^{cyano, -C (= W 3) R} 12, -C (= W 3) OR 12, -C (= W 3) SR 12, ^{-C (= W 3) NR 12} R 13, -S (O) mR 12, -S (O) nNR 12 R 13 or a heterocyclic ring (heterocycle, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkyl carbonyl be in may be substituted); R ⁷ is hydrogen atoms , Alkyl, haloalkyl, alkoxyalkyl or haloalkoxyalkyl; R ⁸ and R ⁹ are each independently a hydrogen atom, an alkyl, haloalkyl, alkoxyalkyl or haloalkoxyalkyl, adjacent R ⁸ and R ⁹ together R ¹⁰ may be alkyl; alkyl may be substituted with halogen, alkoxy or haloalkoxy; alkoxy (alkoxy may be substituted with halogen, alkoxy or haloalkoxy); Alkenyloxy (alkenyloxy may be substituted with halogen, alkoxy or haloalkoxy), alkynyloxy (alkynyloxy may be substituted with halogen, alkoxy or haloalkoxy) or alkoxycarbonyl (alkoxycarbonyl is halogen , Be alkoxy or haloalkoxy may be substituted with); R ¹¹ is optionally substituted hydrogen atoms, at E ³ alkyl, phenyl (wherein phenyl is substituted halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkyl carbonyl Or a heterocycle (the heterocycle may be substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylcarbonyl); R ¹² and R ¹³ are each independently substituted with E ³ Optionally substituted alkyl, alkoxy, haloalkoxy, cycloalkyl or phenyl optionally substituted with J (phenyl may be substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylcarbonyl) and adjacent R ¹² and R ¹³ together may form a ring; W ¹ , W ² and W ³ are each independently an oxygen atom or a sulfur atom; m and n are each independently an integer of 0 to 2; E ¹ is halogen, hydroxy, alkoxy, haloalkoxy, mercapto, alkylthio, Haloalkylthio, alkylsulfonyl, cycloalkyl, amino, monoalkylamino, dialkylamino, cyano, nitro, hydroxycarbonyl, alkoxycarbonyl, alkylcarbonyloxy, trialkylsilyl or heterocycle (heterocycle is halogen, alkyl, haloalkyl, alkoxy E ² may be substituted with halogen, hydroxy, alkoxy, haloalkoxy, cycloalkyl, amino, monoalkylamino, dialkylamino, cyano, nitro, hydroxycarbonyl, Alkoxycarbonyl, trialkylsilyl or heterocycle (heterocyclic ring, halogen, alkyl, haloalkyl, alkoxy, substituted by haloalkoxy or alkylcarbonyl may) be; E ³ is halogen, alkoxy, alkylthio, amino, monoalkylamino Amino, dialkylamino, cycloalkyl, cyano, alkoxycarbonyl, haloalkoxy, haloalkylthio or phenyl (phenyl may be substituted with halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylcarbonyl); J is halogen , Alkyl, haloalkyl, alkoxy, or haloalkoxy].

In the formula (I), the number of substitutions of X as a substituent contained in A may be 1 or 2 or more. In the case of 2 or more, these substituents may be the same or different. The number of substitutions of halogen, alkyl or alkoxy which is a substituent of indanyl or tetrahydronaphthyl contained in A may be 1 or 2 or more, and in the case of 2 or more, these substituents may be the same or different. The number of substitution of Y as a substituent contained in B or X may be 1 or 2 or more, and in the case of 2 or more, these substituents may be the same or different. The number of substitutions of E ¹ , E ² or E ³ as a substituent contained in X, Y, R ³ , R ¹¹ , R ¹² or R ¹³ may be 1 or 2 or more. The groups may be the same or different. The number of substitutions of J as a substituent contained in X, Y, R ³ , R ¹² or R ¹³ may be 1 or 2 or more, and in the case of 2 or more, these substituents may be the same or different. . X, Y, R ⁴ , R ⁵ , R ⁶ , R ¹¹ , R ¹² , R ¹³ , halogen, alkyl, haloalkyl, alkoxy, which are phenyl or heterocyclic substituents contained in E ¹ , E ² or E ³ , The substitution number of haloalkoxy or alkylcarbonyl may be 1 or 2 or more, and in the case of 2 or more, these substituents may be the same or different. The number of substitutions of halogen, alkoxy or haloalkoxy which is a substituent of alkyl, alkoxy, alkenyloxy, alkynyloxy or alkoxycarbonyl contained in R ¹⁰ may be 1 or 2 or more. They may be the same or different.

As the heterocyclic ring in A, B, X, Y, R ⁴ , R ⁵ , R ⁶ , R ¹¹ , E ¹ or E ² , at least one atom selected from the group consisting of O, S and N is 1 3, 5 or 6 membered heterocycles containing ~ 4 are desirable, for example 3 membered heterocycles such as oxiranyl; furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, dioxolanyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, 5-membered heterocycle such as imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl; pyranyl, pyridyl, piperidinyl, dioxanyl, oxazinyl, morpholinyl, thiazinyl, pyridazinyl, pyrazinyl, pyrazinyl, pyrazinyl Le, and a 6-membered heterocyclic ring, such as triazinyl.

  The condensed heterocyclic ring in A or B is an 8- to 10-membered condensed heterocyclic ring containing 1 to 4 atoms selected from the group consisting of O, S and N, such as benzofuranyl, isobenzofuranyl, dihydro Benzofuranyl, dihydroisobenzofuranyl, benzothienyl, isobenzothienyl, dihydrobenzothienyl, dihydroisobenzothienyl, tetrahydrobenzothienyl, indolyl, isoindolyl, benzoxazolyl, benzothiazolyl, indazolyl, benzimidazolyl, benzodioxolanyl , Benzodioxanyl, chromenyl, chromanyl, isochromanyl, chromonyl, chromonyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolidinyl, imidazopyridid , Naphthyridinyl, pteridinyl, dihydro benzoxazinyl, dihydro benzoxazolyl nonyl, dihydrobenzo oxadiazole nonyl, benzothiadiazole oxa sulfonyl and the like.

The alkyl or alkyl moiety in A, X, Y, R ^{1 to} R ³ , R ^{6 to} R ¹³ , E ^{1 to} E ³ or J may be either linear or branched, and specific examples thereof , methyl, ethyl, propyl, isopropyl, butyl, tert- butyl, pentyl, hexyl, and the like as a _{C 1-7,} such as heptyl.

Examples of the cycloalkyl or cycloalkyl moiety in X, Y, R ^{1 to} R ³ , R ⁶ , R ¹² , R ¹³ or E ^{1 to} E ³ include those having 3 to 6 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl Etc. Specific examples of the 3- to 6-membered saturated carbocycle formed by combining R ¹ and R ² include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

Examples of the alkenyl or alkenyl moiety in X, Y, R ^{1 to} R ³ or R ¹⁰ include linear or branched ones having 2 to 7 carbon atoms such as vinyl, 1-propenyl, allyl, isopropenyl, 1- Examples include butenyl, 1,3-butadienyl, 1-hexenyl, 1-heptenyl and the like. In addition, as the alkynyl or alkynyl moiety in X, Y, R ^{1 to} R ³ or R ¹⁰ , linear or branched ones having 2 to 7 carbon atoms such as ethynyl, 2-butynyl, 2-pentynyl, 3 -Hexynyl, 4-dimethyl-2-pentynyl and the like.

Examples of the halogen in A, X, Y, R ^{1 to} R ¹³ , E ^{1 to} E ³ or J or the halogen as a substituent include each atom of fluorine, chlorine, bromine or 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.
The definition of the substituent A ^α or X ^{α in} the formula (I-α) is in accordance with the definition of the substituent A or X in the formula (I).

  The salt of the acid amide derivative of the formula (I) or (I-α) includes any agriculturally acceptable salt, for example, an alkali metal salt such as sodium salt or potassium salt; magnesium Examples thereof include alkaline earth metal salts such as salts and calcium salts; inorganic acid salts such as hydrochlorides, perchlorates, sulfates and nitrates; organic acid salts such as acetates and methanesulfonates.

The acid amide derivative of the formula (I) or (I-α) has various isomers such as optical isomers and geometric isomers. In the present invention, both the isomers and the isomer mixtures are included. included. The present invention also includes various isomers other than those described above within the scope of technical common sense in the technical field. In addition, depending on the type of isomer, there may be a chemical structure different from the formula (I) or (I-α), but those skilled in the art can fully recognize that they are in an isomer relationship. Therefore, it is clear that it is within the scope of the present invention.
The acid amide derivative of the above formula (I) or (I-α) or a salt thereof should be produced according to the following reactions [A] to [K], [U] to [W] and a usual salt production method. Can do.

In the reaction [A], A, B, R ¹ and R ² are as described above, Z is hydroxy, alkoxy or halogen, and the halogen includes fluorine, chlorine, bromine or iodine atoms.
Reaction [A] can be normally performed in presence of a base and a solvent.
Examples of the base include alkali metals such as sodium and potassium; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide; carbonates such as sodium carbonate and potassium carbonate; sodium bicarbonate and bicarbonate. Bicarbonates such as potassium; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as monomethylamine, dimethylamine and triethylamine; One or two or more kinds can be appropriately selected from pyridines such as pyridine and 4-dimethylaminopyridine; and organic lithium compounds such as methyllithium, n-butyllithium, and lithium diisopropylamide. The base can be used in an amount of 1 to 3 mol, desirably 1 to 2 mol per mol of the compound of formula (II).

  The solvent may be any solvent as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, Aliphatic hydrocarbons such as hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N -One or more kinds of polar aprotic solvents such as methylpyrrolidone, pyridine, acetonitrile, propionitrile; ketones such as acetone and methyl ethyl ketone can be appropriately selected.

Reaction [A] can be carried out in the presence of a dehydrating condensing agent, if necessary. Examples of the dehydrating condensing agent include N, N′-dicyclohexylcarbodiimide, chlorosulfonyl isocyanate, N, N′-carbonyldiimidazole, trifluoroacetic anhydride and the like.
The reaction [A] can be carried out usually at 0 to 100 ° C., preferably 0 to 50 ° C., and the reaction time can be usually about 0.5 to 48 hours, preferably about 1 to 24 hours.

During reaction (B), A, B, R ¹ and R ² are as defined above, R ^3a is substituted with E ¹ alkyl which may be substituted by, an alkenyl, E ¹ be replaced by E ¹ Optionally alkynyl, hydroxy, cyanooxy, alkoxy optionally substituted with E ¹ , cycloalkyl optionally substituted with J, cycloalkyloxy optionally substituted with J, cycloalkylthio optionally substituted with J, Cyano, formyl, -C (= W ³ ) R ¹¹ , -C (= W ³ ) OR ¹² , -C (= W ³ ) SR ¹² , -C (= W ³ ) NR ¹² R ¹³ , -S (O ) mR ¹² or —S (O) nNR ¹² R ¹³ (E ¹ , J, R ¹¹ , R ¹² , R ¹³ , W ³ , m and n are as described above), T is halogen, Includes fluorine, chlorine, bromine or iodine atoms.

Reaction [B] can be normally performed in presence of a base and a solvent.
Examples of the base include alkali metals such as sodium and potassium; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide; carbonates such as sodium carbonate and potassium carbonate; sodium bicarbonate and bicarbonate. Bicarbonates such as potassium; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as monomethylamine, dimethylamine and triethylamine; One or two or more kinds can be appropriately selected from pyridines such as pyridine and 4-dimethylaminopyridine. The base can be used in an amount of 1 to 3 times mol, preferably 1 to 1.5 times mol, of the compound of formula (I-1).

The solvent may be any solvent as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, Aliphatic hydrocarbons such as hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N A polar aprotic solvent such as methylpyrrolidone or pyridine; a nitrile such as acetonitrile, propionitrile, or acrylonitrile; a ketone such as acetone or methylethylketone; It can be appropriately selected or more species.
The reaction [B] can be usually carried out at 0 to 100 ° C., preferably 0 to 50 ° C., and the reaction time can be usually about 1 to 300 hours, preferably about 1 to 150 hours.

During reaction (C), A, R ¹ and R ² are as defined above, B ¹ is a fused heterocyclic ring substituted with a heterocycle or -CO ₂ H substituted with -CO ₂ H, wherein ( V) is a dicarboxylic acid anhydride of Q (phenyl, heterocycle or fused heterocycle).
Reaction [C] can be normally performed in presence of a solvent. The solvent may be any solvent as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane. Aliphatic hydrocarbons such as hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, Polar aprotic solvents such as N-methylpyrrolidone and pyridine; nitriles such as acetonitrile, propionitrile and acrylonitrile; ketones such as acetone and methyl ethyl ketone; methanol; Ethanol, propanol, tert- butanol alcohols from such one or more suitably selected such as.

Reaction [C] can be carried out in the presence of a base, if necessary. Examples of the base include alkali metals such as sodium and potassium; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide; carbonates such as sodium carbonate and potassium carbonate; sodium bicarbonate, Bicarbonates such as potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as monomethylamine, dimethylamine and triethylamine 1 type, or 2 or more types can be appropriately selected from pyridines such as pyridine and 4-dimethylaminopyridine. The base can be used in an amount of 1 to 3 moles, preferably 1 to 1.5 moles relative to the compound of formula (II).
The reaction [C] can usually be carried out at 0 to 150 ° C., preferably 0 to 80 ° C., and the reaction time is usually about 0.5 to 96 hours, preferably about 1 to 48 hours. .

During reaction (D), A, R ¹ and R ² are as defined above, B ² is a fused heterocyclic ring substituted by a heterocyclic or Y ² substituted by Y ^2, B ³ is Y ³ A substituted heterocyclic ring or a condensed heterocyclic ring substituted with Y ³ , Y ² is a chlorine, bromine or iodine atom, and Y ³ is a heterocyclic ring (which is a halogen, alkyl, haloalkyl, alkoxy or Optionally substituted with haloalkoxy).
Reaction [D] can be normally performed in presence of a catalyst, a base, a solvent, and an inert gas.
The catalyst may be one or more of palladium complexes such as tetrakis (triphenylphosphine) palladium (0), bis (dibenzylideneacetone) palladium (0), tris (dibenzylideneacetone) dipalladium (0), etc. Can be appropriately selected.
Examples of the base include carbonates such as sodium carbonate, potassium carbonate, and calcium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide, and the like. Or 2 or more types can be selected suitably. A base is 1-20 times mole with respect to the compound of Formula (I-4), 1-10 times mole can be used desirably.

  The solvent may be any solvent as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, Aliphatic hydrocarbons such as hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N -Polar aprotic solvents such as methylpyrrolidone and pyridine; Nitriles such as acetonitrile, propionitrile and acrylonitrile; Ketones such as acetone and methyl ethyl ketone; Methanol, ethyl Nord, propanol, tert- alcohols such as butanol; water one or more of such may be suitably selected.

For example, nitrogen gas or argon gas can be used as the inert gas.
The reaction [D] can usually be carried out at 0 to 150 ° C., preferably 15 to 100 ° C., and the reaction time is usually about 0.5 to 96 hours, preferably about 1 to 48 hours. .

During reaction (E), A, R ¹ and R ² are as defined above, B ⁴ is a fused heterocyclic ring substituted with a heterocycle or -CO ₂ H substituted with -CO ₂ H, B ⁵ is a condensed heterocyclic group substituted by -CO ₂ heterocycle or -CO substituted with R ^8a ₂ R ^8a, R ^8a is alkyl, haloalkyl, alkoxyalkyl or haloalkoxyalkyl.
The 1st process in reaction [E] can be performed in presence of a chlorinating agent. As the chlorinating agent, for example, one or more can be appropriately selected from thionyl chloride, oxalyl chloride, phosphorus pentachloride and the like.
The 1st process in reaction [E] can be performed in presence of a solvent as needed. The solvent may be any solvent as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane. 1 type or 2 types or more are appropriately selected from aliphatic hydrocarbons such as hexane, hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; it can.

The reaction in the first step in the reaction [E] can usually be carried out at 0 to 200 ° C., preferably 15 to 150 ° C., and the reaction time is usually about 0.1 to 72 hours, preferably about 0.5 to 3 hours. It can be.
The 2nd process in reaction [E] can be performed in presence of a base as needed. The base may be, for example, an alkali metal such as sodium or potassium; an alkali metal alkoxide such as sodium methoxide, sodium ethoxide, or potassium tertiary butoxide; a carbonate such as sodium carbonate or potassium carbonate; Bicarbonates such as potassium carbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as monomethylamine, dimethylamine and triethylamine 1 type (s) or 2 or more types can be suitably selected from pyridines, such as pyridine and 4-dimethylaminopyridine. The base can be used in an amount of 1 to 5 times mol, preferably 1 to 2 times mol for the compound of formula (I-6).

The 2nd process in reaction [E] can be performed in presence of a solvent as needed. The solvent may be any solvent as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane. Aliphatic hydrocarbons such as hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, 1 type of polar aprotic solvents such as N-methylpyrrolidone and pyridine; nitriles such as acetonitrile, propionitrile and acrylonitrile; ketones such as acetone and methyl ethyl ketone Two or more suitably selected. In this reaction, an excessive amount of the compound of formula (VII) can be used as a solvent.
The reaction in the second step in the reaction [E] can be carried out usually at 0 to 100 ° C., preferably 0 to 50 ° C., and the reaction time is usually about 0.1 to 48 hours, preferably about 0.5 to 6 hours. It can be.

In the reaction [F], A, B ⁴ , B ⁵ , R ¹ , R ² and R ^8a are as described above, and the reaction [F] can be carried out usually in the presence of a catalyst or a dehydrating condensing agent.
The catalyst can be appropriately selected from one or more of mineral acids such as hydrochloric acid and sulfuric acid; organic acids such as p-toluenesulfonic acid; Lewis acids such as boron trifluoride etherate.
As the dehydrating condensing agent, one or more kinds of N, N′-dicyclohexylcarbodiimide, chlorosulfonyl isocyanate, N, N′-carbonyldiimidazole, trifluoroacetic anhydride and the like can be appropriately selected.

Reaction [F] can be performed in presence of a solvent as needed. The solvent may be any solvent as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane. Aliphatic hydrocarbons such as hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, Polar aprotic solvents such as N-methylpyrrolidone and pyridine; nitriles such as acetonitrile, propionitrile and acrylonitrile; ketones such as acetone and methyl ethyl ketone; methanol; Ethanol, propanol, tert- butanol alcohols from such one or more suitably selected such as. In this reaction, an excessive amount of the compound of formula (VII) can be used as a solvent.
The reaction [F] can be carried out usually at 0 to 200 ° C., preferably 0 to 100 ° C., and the reaction time is usually about 0.1 to 96 hours, preferably about 0.5 to 24 hours.

During reaction ^{(G), A, B 4, R 1} , R 2, R 8 and R ⁹ are as defined above, B ⁶ is a heterocyclic ring or -CONR ⁸ R ⁹ substituted with -CONR ⁸ R ⁹ A substituted condensed heterocyclic group (R ⁸ and R ⁹ are as described above).
The 1st process in reaction [G] can be performed according to the 1st process of the said reaction [E].
The 2nd process in reaction [G] can be performed in presence of a base as needed. The base may be, for example, an alkali metal such as sodium or potassium; an alkali metal alkoxide such as sodium methoxide, sodium ethoxide, or potassium tertiary butoxide; a carbonate such as sodium carbonate or potassium carbonate; Bicarbonates such as potassium carbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as monomethylamine, dimethylamine and triethylamine 1 type (s) or 2 or more types can be suitably selected from pyridines, such as pyridine and 4-dimethylaminopyridine. The base can be used in an amount of 1 to 10 moles, preferably 1 to 2 moles compared to the compounds of the formula (I-6).

The 2nd process in reaction [G] can be performed in presence of a solvent as needed. The solvent may be any solvent as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane. Aliphatic hydrocarbons such as hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, Polar aprotic solvents such as N-methylpyrrolidone and pyridine; nitriles such as acetonitrile, propionitrile and acrylonitrile; ketones such as acetone and methyl ethyl ketone; Or more suitably selected.
The reaction in the second step in the reaction [G] can be carried out usually at 0 to 100 ° C., preferably 0 to 50 ° C., and the reaction time is usually about 0.1 to 48 hours, preferably about 0.5 to 6 hours. It is.

In the reaction [H], A, B ⁴ , B ⁶ , R ¹ , R ² , R ⁸ and R ⁹ are as described above.
The reaction [H] can be usually performed in the presence of a dehydration condensing agent and a solvent.
As the dehydrating condensing agent, one or more kinds of N, N′-dicyclohexylcarbodiimide, chlorosulfonyl isocyanate, N, N′-carbonyldiimidazole, trifluoroacetic anhydride and the like can be appropriately selected.
The solvent may be any solvent as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, Aliphatic hydrocarbons such as hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N A polar aprotic solvent such as methylpyrrolidone or pyridine; a nitrile such as acetonitrile, propionitrile, or acrylonitrile; a ketone such as acetone or methylethylketone; It can be appropriately selected or more species.
The reaction [H] can be carried out usually at 0 to 200 ° C., preferably 0 to 100 ° C., and the reaction time can be usually about 0.1 to 96 hours, preferably about 0.5 to 24 hours. .

In the reaction [I], A, B ⁵ , B ⁶ , R ¹ , R ² , R ⁸ and R ⁹ are as described above.
Reaction [I] can be normally performed in presence of a solvent. The solvent may be any solvent as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane. Aliphatic hydrocarbons such as hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, Polar aprotic solvents such as N-methylpyrrolidone and pyridine; nitriles such as acetonitrile, propionitrile and acrylonitrile; ketones such as acetone and methyl ethyl ketone; methanol; Ethanol, propanol, alcohols such as tert- butanol; suitably selecting such one or more of water. In this reaction, an excessive amount of the compound of formula (VIII) can be used as a solvent.
The reaction [I] can be carried out usually at 0 to 150 ° C., preferably 0 to 80 ° C., and the reaction time is usually about 0.1 to 48 hours, preferably about 0.5 to 24 hours. .

During reaction (J), B is as defined above, A ¹ is phenyl substituted by -OR ^4, benzyl substituted by -OR ^4, substituted naphthyl, -OR ⁴ substituted by -OR ⁴ A heterocyclic ring or a condensed heterocyclic ring substituted with —OR ⁴ (R ⁴ is as described above), and A ² is phenyl substituted with —OH, benzyl substituted with —OH, and substituted with —OH. Naphthyl, a heterocyclic ring substituted with —OH or a condensed heterocyclic ring substituted with —OH, wherein R ^1a and R ^2a are each alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl, cyanoalkyl, alkoxycarbonylalkyl , Alkenyl, haloalkenyl, alkoxyalkenyl, alkynyl, haloalkynyl, alkoxyalkynyl, cycloalkyl, halocycloalkyl, (alkyl) cycloalkyl , (Haloalkyl) cycloalkyl or cyano, and R ^1a and R ^2a may combine to form a 3- to 6-membered saturated carbocycle, and M is sodium or potassium.

Reaction [J] can be normally performed in presence of a solvent. The solvent may be any solvent as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane. Aliphatic hydrocarbons such as hexane, cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, dimethoxyethane; polar non-polar such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone, pyridine Protic solvents; nitriles such as acetonitrile, propionitrile, acrylonitrile; ketones such as acetone, methyl ethyl ketone; methanol, ethanol, propanol, tert-butanol Una alcohols; water one or more of such may be suitably selected.
The reaction [J] can usually be carried out at 0 to 100 ° C., preferably 20 to 80 ° C., and the reaction time can be usually about 0.1 to 24 hours, preferably about 0.1 to 12 hours. .

In the reaction [K], A ¹ , A ² , B, R ^1a , R ^2a and R ⁴ are as described above, and G is each atom of chlorine, bromine or iodine.
Reaction [K] can be normally performed in presence of a base and a solvent.
Bases include, for example, alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium tertiary butoxide; carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; water Metal hydroxides such as sodium oxide and potassium hydroxide; Metal hydrides such as sodium hydride and potassium hydride; Amines such as monomethylamine, dimethylamine and triethylamine; Pyridine and 4-dimethylaminopyridine 1 type, or 2 or more types are appropriately selected from various pyridines and the like. The base can be used in an amount of 1 to 2 mols, preferably 1 to 1.5 mols per mol of the compound of formula (I-10).

The solvent may be any solvent as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, Aliphatic hydrocarbons such as hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N A polar aprotic solvent such as methylpyrrolidone or pyridine; a nitrile such as acetonitrile, propionitrile, or acrylonitrile; a ketone such as acetone or methylethylketone; It can be appropriately selected or more species.
The reaction [K] can be carried out usually at −20 to 100 ° C., preferably 0 to 50 ° C., and the reaction time is usually about 0.1 to 24 hours, preferably about 0.1 to 12 hours.
The compound of the formula (II) used in the reaction [A] or [C] can be produced according to the following reactions [L] to [N].

In the reaction [L], A, R ¹ and R ² are as described above. In the reaction [L], a salt of the compound (II) can be produced according to a post-treatment of the reaction or a normal salt formation reaction.
Reaction [L] can be normally performed in presence of an oxidizing agent and water.
Examples of the oxidizing agent include potassium ferricyanide. An oxidizing agent is 1-10 times mole with respect to the compound of Formula (XII), Preferably 1-5 times mole can be used.
Reaction [L] can be performed in presence of a solvent as needed. The solvent may be any solvent inert to the reaction, for example, ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; dimethyl sulfoxide, One or two or more polar aprotic solvents such as sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile and propionitrile; ketones such as acetone and methyl ethyl ketone can be appropriately selected. Moreover, the water used by reaction [L] can serve as a solvent by using it excessively.
The reaction [L] can be carried out usually at 20 to 150 ° C., preferably 50 to 100 ° C., and the reaction time is usually about 0.5 to 30 hours, preferably about 1 to 20 hours.

In the reaction [M], A, R ¹ and R ² are as described above. In the reaction [M], a salt of the compound (II) can be produced according to a post-treatment of the reaction or a normal salt formation reaction.
The cyclization reaction of reaction [M] can usually be performed in the presence of a base and a solvent.
Examples of the base include alkali metals such as sodium and potassium; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide; metal hydrides such as sodium hydride and potassium hydride, and the like. Or 2 or more types are selected suitably. The base can be used in an amount of 1 to 3 times mol, preferably 1 to 1.5 times mol for the compound of formula (XIII).

The solvent may be any solvent that is inert to the reaction, for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; One or more kinds can be appropriately selected from alcohols such as methanol, ethanol, propanol and tert-butanol; nitriles such as acetonitrile, propionitrile and acrylonitrile.
The reaction of the cyclization reaction of the reaction [M] can be carried out usually at 0 to 150 ° C., preferably 30 to 100 ° C., and the reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours. can do.

The hydrolysis reaction of reaction [M] can be carried out according to a general hydrolysis reaction, and can usually be carried out in the presence of an acid or a base and a solvent.
Examples of the acid include hydrogen chloride and sulfuric acid. Examples of the base include metal hydroxides such as sodium hydroxide and potassium hydroxide.
The solvent may be any solvent as long as it is inert to the reaction. For example, alcohols such as methanol, ethanol, propanol and tert-butanol; nitriles such as acetonitrile, propionitrile and acrylonitrile; acetone and methyl ethyl ketone 1 type or 2 types or more can be suitably selected from water etc .;
The reaction of the reaction [M] can be carried out usually at 0 to 100 ° C., preferably 20 to 80 ° C., and the reaction time is usually about 0.1 to 12 hours, preferably about 0.1 to 1 hour. be able to.

In the reaction [N], A, R ¹ and R ² are as described above. In the reaction [N], a salt of the compound (II) can be produced according to a post-treatment of the reaction or a normal salt formation reaction.
Examples of the reduction reaction [N] include catalytic reduction, reduction with metal hydride (sodium borohydride, lithium aluminum hydride, etc.); reduction with triphenylphosphine, dimethyl sulfide or diphenyl sulfide; iron, copper and the like Reduction in a reaction system composed of a metal and a carboxylic acid such as formic acid or acetic acid can be mentioned. The catalytic reduction can be usually performed by using platinum, platinum oxide, platinum black, Raney nickel, palladium, palladium carbon, rhodium, rhodium-alumina or the like as a catalyst in a hydrogen atmosphere.

Reaction [N] can be normally performed in presence of a solvent. The solvent may be any solvent as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as hexane and cyclohexane; dioxane, tetrahydrofuran, Ethers such as diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; nonpolar such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile and propionitrile Protonic solvents; ketones such as acetone and methyl ethyl ketone; alcohols such as methanol, ethanol, propanol and tert-butanol; one or two or more can be appropriately selected.
The reaction [N] can be carried out usually at 0 to 150 ° C., preferably 0 to 80 ° C., and the reaction time is usually about 0.5 to 96 hours, preferably about 0.5 to 48 hours.
The compound of the formula (XIII) used in the reaction [M] can be produced according to the following reaction [O].

In the reaction [O], A, R ¹ and R ² are as described above.
Reaction [O] can be performed in presence of a solvent as needed. The solvent may be any solvent that is inert to the reaction, for example, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane. Aliphatic hydrocarbons such as cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; alcohols such as methanol, ethanol, propanol and tert-butanol 1 type or 2 or more types can be selected as appropriate from polar aprotic solvents such as acetonitrile and propionitrile; ketones such as acetone and methyl ethyl ketone.

The methyl iodide of the reaction [O] can be used in an amount of 1 to 10 times mol, preferably 1 to 3 times mol for the compound of formula (VII). Further, when methyl iodide is used in excess, it can also serve as a solvent.
The reaction [O] can be carried out usually at 0 to 100 ° C., preferably 10 to 50 ° C., and the reaction time is usually about 0.5 to 48 hours, preferably about 1 to 24 hours.
The compound of the formula (XIV) used in the reaction [N] can be produced according to the following reaction [P].

In the reaction [P], A, R ¹ and R ² are as described above, and U is each atom of chlorine or bromine.
The reaction [P] can be carried out in the presence of an azidating agent. As the azidating agent, one or two or more kinds can be appropriately selected from, for example, sodium azide, potassium azide, trimethylsilyl azide and the like.

Reaction [P] can be normally performed in presence of a solvent. The solvent may be any solvent inert to the reaction, for example, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, Aliphatic hydrocarbons such as cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide and N-methyl Polar aprotic solvents such as pyrrolidone, pyridine, acetonitrile, propionitrile; ketones such as acetone and methyl ethyl ketone; such as methanol, ethanol, propanol and tert-butanol Alcohols such; water one or more of such may be suitably selected.
The reaction [P] can usually be carried out at 0 to 150 ° C., preferably 20 to 90 ° C., and the reaction time is usually about 0.1 to 96 hours, preferably about 0.5 to 12 hours.
The compound of the formula (XV) used in the reaction [O] can be produced according to the following reaction [Q].

In the reaction [Q], A, R ¹ and R ² are as described above.
The reaction [Q] can be carried out according to a general hydrazone synthesis reaction, and can be carried out in the presence of a dehydrating agent and / or a catalyst, if necessary.
Examples of the dehydrating agent include molecular sieves. The dehydrating agent is usually used in an amount of 1 to 30 times, preferably 5 to 10 times the weight of the compound of the formula (XII).
Examples of the catalyst include titanium tetrachloride.
The dimethylhydrazine in the reaction [Q] is usually used in an amount of 1 to 30 times mol, preferably 5 to 10 times mol for the compound of the formula (XII).
The reaction [Q] can usually be carried out at 20 to 150 ° C., preferably 50 to 120 ° C., and the reaction time is usually about 5 to 200 hours, preferably about 24 to 120 hours. .
The compound of the formula (XVI) used in the reaction [P] can be produced according to the following reaction [R].

In the reaction [R], A, R ¹ , R ² and U are as described above.
Reaction [R] can be performed in presence of a chlorinating agent or a brominating agent. As the chlorinating agent, for example, one or more kinds are appropriately selected from chlorine, N-chlorosuccinimide, and the like. As the brominating agent, for example, bromine, N-bromosuccinimide, phenyltrimethylammonium tribromide, and the like One type or two or more types can be appropriately selected.

  Reaction [R] can be normally performed in presence of a solvent. The solvent may be any solvent that is inert to the reaction, for example, aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, cyclohexane; dioxane, tetrahydrofuran Ethers such as diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone and pyridine; One or two or more of organic acids such as propionic acid and water can be appropriately selected.

Reaction [R] can be carried out in the presence of a base, if necessary. Examples of the base include lithium diisopropylamide. The base can be used in an amount of 1 to 2 mols, preferably 1 to 1.2 mols per mol of the compound of formula (XII).
When the reaction is carried out in the presence of a base, one or more kinds of solvents can be appropriately selected from ethers such as tetrahydrofuran and diethyl ether.
In the reaction [R], an organic acid such as acetic acid or propionic acid or a Lewis acid such as aluminum chloride can be used as a catalyst, if necessary. Moreover, it can serve as a catalyst by using excessively the organic acid as a solvent.

The reaction [R] can be carried out usually at −100 to 150 ° C., preferably at −78 to 110 ° C., and the reaction time is usually about 0.1 to 48 hours, preferably about 0.5 to 24 hours. However, when carried out in the presence of a base, it can usually be carried out at -100 to 0 ° C, preferably -78 to -20 ° C, and the reaction time is usually about 0.1 to 12 hours, preferably about 0.5 to 6 hours. When it is carried out in the presence of an acid, it can be usually carried out at 0 to 150 ° C., preferably 20 to 110 ° C., and the reaction time is usually about 0.1 to 48 hours, preferably 1 to It can be about 24 hours.
The compound of the formula (XII) used in the reaction [Q] is a known compound, or can be produced according to the following reactions [S] to [T] or a method analogous thereto.

In the reaction [S], R ¹ and R ² are as described above, Z is an oxygen atom, sulfur atom, or —C (G ¹ ) G ² —, and X ^a is a hydrogen atom, chlorine atom or alkyl. X ^{a ′} is a chlorine atom or alkyl, X ^b , X ^c , X ^d , X ^e , G ¹ and G ² are each independently a hydrogen atom, a fluorine atom or a chlorine atom, and V is a bromine atom or An iodine atom, j is 0 or 1, L is a leaving group, more specifically a halogen such as a chlorine atom or a bromine atom; an alkoxy such as methoxy or ethoxy; a dialkyl such as dimethylamino or diethylamino Amino; N-methoxy-N-methylamino or aziridinyl optionally substituted with alkyl.
The 1st process of reaction [S] can be normally performed in presence of a base and a solvent.
The base can be appropriately selected from organic lithium compounds such as lithium diisopropylamide. The base can be used in an amount of 1 to 2 moles, preferably 1 to 1.5 moles based on the compound of the formula (XVII-1) or (XVII-2).

The solvent may be any solvent as long as it is inert to the reaction. For example, one or more solvents can be appropriately selected from ethers such as dioxane, tetrahydrofuran and diethyl ether.
Examples of the chlorinating agent used in the first step of the reaction [S] include N-chlorosuccinimide.
The formula: X ^{a ′} -I used in the first step of the reaction [S] can be used in an amount of 1 to 10 times, preferably 1 to 5 times the amount of the compound of the formula (XVII-1) or (XVII-2). . In addition, the chlorinating agent used in the first step of the reaction [S] can be used in an amount of 1 to 5 times, preferably 1 to 3 times the amount of the compound of the formula (XVII-1) or (XVII-2).
The 1st process of reaction [S] can be performed in presence of an inert gas as needed. The inert gas can be appropriately selected from, for example, nitrogen gas and argon gas.
The first step of the reaction [S] can be usually performed at −100 to 50 ° C., preferably −70 to 25 ° C., and the reaction time is usually about 1 to 48 hours, preferably about 1 to 20 hours. can do.

The 2nd process of reaction [S] can be normally performed in presence of a base and a solvent.
The base can be appropriately selected from one or more of organic lithium compounds such as methyllithium and n-butyllithium; Grignard compounds such as isopropylmagnesium chloride. The base can be used in an amount of 1 to 2 times, preferably 1 to 1.5 times the amount of the compound of the formula (XVII-1), (XVII-2), (XVIII-1) or (XVIII-2).
The solvent may be any solvent as long as it is inert to the reaction. For example, one or more solvents can be appropriately selected from ethers such as dioxane, tetrahydrofuran and diethyl ether.
The compound of the formula (XIX) used in the second step of the reaction [S] is 1 to 3 times the compound of the formula (XVII-1), (XVII-2), (XVIII-1) or (XVIII-2) Mole, preferably 1 to 1.5 times mol can be used.
The 2nd process of reaction [S] can be performed in presence of an inert gas as needed. The inert gas can be appropriately selected from, for example, nitrogen gas and argon gas.
The second step of the reaction [S] can usually be carried out at −100 to 50 ° C., preferably −70 to 25 ° C., and the reaction time is usually about 1 to 48 hours, preferably about 1 to 20 hours. can do.

In the reaction [T], R ¹ , R ² , Z, X ^a , X ^{a ′} , X ^b , X ^c , X ^d , X ^e , V and j are as described above.
The 1st process of reaction [T] can be normally performed in presence of a base and a solvent.
The base can be appropriately selected from one or more of organic lithium compounds such as methyllithium and n-butyllithium; Grignard compounds such as isopropylmagnesium chloride. The base can be used in an amount of 1 to 2 times, preferably 1 to 1.5 times the amount of the compound of the formula (XVII-1), (XVII-2), (XVIII-1) or (XVIII-2).
The solvent may be any solvent as long as it is inert to the reaction. For example, one or more solvents can be appropriately selected from ethers such as dioxane, tetrahydrofuran and diethyl ether.
The formula (XX) used in the first step of the reaction [T] is 1 to 3 moles relative to the compound of the formula (XVII-1), (XVII-2), (XVIII-1) or (XVIII-2), Desirably, it can be used in an amount of 1 to 1.5 moles.

The 1st process of reaction [T] can be performed in presence of an inert gas as needed. The inert gas can be appropriately selected from, for example, nitrogen gas and argon gas.
The first step of the reaction [T] can be carried out usually at −100 to 50 ° C., preferably −70 to 25 ° C., and the reaction time is usually about 1 to 48 hours, preferably about 1 to 20 hours. can do.
The 2nd process of reaction [T] can be normally performed in presence of an oxidizing agent and a solvent.
The oxidizing agent can be appropriately selected from one or more of pyridinium chlorochromate and manganese dioxide. The oxidizing agent can be used in an amount of 1 to 10 times mol, preferably 1 to 3 times mol, of the compound of formula (XXI-1) or (XXI-2).
The solvent may be any solvent as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, cyclohexane 1 type (s) or 2 or more types can be suitably selected from such aliphatic hydrocarbons.
The second step of the reaction [T] can be usually carried out at 0 to 150 ° C., preferably 20 to 100 ° C., and the reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours. Can do.

In the reaction [U], A, B, R ¹ , R ² and Z are as described above.
Reaction [U] can be carried out according to the above reaction [A].

In the reaction [V], A, B, R ¹ , R ² , U and Z are as described above. Examples of the thiocarbonylating agent include Lawesson's reagent and diphosphorus pentasulfide. Reaction [V] consists of five stages of reaction as shown in (1) to (5) in the above flow, and the reaction conditions for each reaction will be described below.
The reaction (1) can usually be performed in the presence of a solvent. The solvent may be any solvent that is inert to the reaction, such as aromatic hydrocarbons such as benzene, toluene, and xylene; Aliphatic hydrocarbons; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran, dioxane; carbon disulfide and the like can be appropriately selected from one or more.

The reaction (1) can be carried out usually at -20 to 150 ° C, preferably 0 to 110 ° C, and the reaction time can be usually 0.1 to 48 hours.
In the reaction (1), the thiocarbonylating agent can be used in an amount of 0.4 to 2 moles compared to the compound of the formula (XII).
The reaction (2) can be carried out according to the above reaction [R].
The reaction (3) can be carried out according to the above reaction [P].
The reaction (4) can be carried out according to the above reaction [N].
The reaction (5) can be carried out according to the above reaction [A].

In the reaction [W], A, B, R ¹ , R ² and Z are as described above.
Reaction [W] can be carried out according to the above reaction [A].
Incidentally, the acid amide derivative of the formula (I) or a salt thereof can be produced by referring to the method disclosed in WO2001 / 60783 or WO2003 / 27059, if necessary.

  A bactericidal composition containing an acid amide derivative of the formula (I) or a salt thereof as an active ingredient (hereinafter abbreviated as the composition of the present invention) can control harmful fungi at a low dose, for example, for agricultural and horticultural use Useful as a bactericidal composition.

Desirable embodiments of the composition of the present invention will be described below.
The composition of the present invention is useful as a bactericidal composition capable of controlling harmful fungi at a low dose, and particularly useful as a bactericidal composition for agriculture and horticulture. When used as an agricultural and horticultural bactericidal composition, the composition of the present invention is a harmful fungus belonging to, for example, oomycetes, ascomycetes, basidiomycetes, incomplete fungi (Deuteromycetes), etc. It is particularly effective for controlling harmful fungi belonging to Ascomycetes and Deuteromycetes.

Specific examples of the harmful fungi include the following.
As oomycetes, potato or tomato plague ( Phytophthora infestans ), phytophytra ( Phytophthora ) genus such as tomato gray plague ( Phytophthora capsici ); Pseudoperonospora cubensis Pseudoperonospora ) genus; Plasmopara genus such as Plasmopara viticol ; Pythium graminicola ; Pythium genus such as wheat brown snow rot Pythium iwayamai Is mentioned.

As ascomycetes, Erysiphe such as wheat powdery mildew (Erysiphe graminis) (Erysiphe) genus; cucumber powdery mildew (Sphaerotheca fuliginea), Sphaerotheca (Sphaerotheca) such as strawberry powdery mildew (Sphaerotheca humuli) genus; grape udon Unshinyura such as this fungus (Uncinula necator) (Uncinula) genus; Podosufaera such as apple powdery mildew (Podosphaera leucotricha) (Podosphaera) genus; pea褐紋fungus (Mycosphaerella pinodes), apple black spot fungus (Mycosphaerella pomi), banana black Sigatoka fungus (Mycosphaerella musicola), oysters circle star deciduous fungus (Mycosphaerella nawae), Mikosufaerera (Mycosphaerella) species such as the strawberry bull's-eye fungus (Mycosphaerella fragariae); apple scab (Venturia inaequalis), pear scab (Venturia nashicola) Venturia such as (Venturia Genus; barley net plaques fungi (Pyrenophora teres), Pirenohora (Pyrenophora) spp such as barley Madaraha fungi (Pyrenophora graminea); bean Sclerotinia sclerotiorum, cucumber Sclerotinia sclerotiorum, cabbage Sclerotinia cinerea, Chinese cabbage Sclerotinia cinerea, pepper bacterial Sclerotinia sclerotiorum , Sclerotinia borealis , wheat tomato, Sclerotinia minor , alfalfa nuclei, such as nuclei, pepper, or onion (Sclerotinia trifoliorum) sclerotinia (Sclerotinia) such as the genus; co Clio bolus (Cochliobolus, such as rice sesame leaf spot fungus (Cochliobolus miyabeanus); Botoriorinia (Botryolinia) genus, such as peanut small Sclerotinia cinerea (Botryolinia arachidis) Genus; Didymella bryoniae , such as Didymella ; Com Gibberella such as formic Fusarium fungus (Gibberella zeae) (Gibberella) spp; grape black痘病bacteria (Elsinoe ampelina), Erushinoe (Elsinoe) genus, such as citrus scab pathogen (Elsinoe fawcettii); citrus black spot fungus (Diaporthe citri) , Diaporuse such as grapes branch膨病bacteria (Diaporthe) belonging to the genus (Diaporthe sp.); Ringomoniria fungus (Monilinia mali), Monirinia (Monilinia), such as peach ash star fungus (Monilinia fructicola) genus; grapes evening rot fungus (Glomerella Guromerera (Glomerella) species, such as the cingulata), and the like.

As basidiomycetes, Rhizoctonia genus such as rice rot ( Rhizoctonia solani ); Ustilago genus such as Ustilago nuda ; Puccinia coronata , wheat red rust Puccinia recondita , Puccinia genus such as wheat yellow rust fungus ( Puccinia striiformis ); Tifah genus such as wheat or barley snow rot bacterium ( Typhula incarnata , Typhula ishikariensisis ) It is done.

As Deuteromycetes, wheat glume blotch fungus (Septoria nodorum), Septoria (Septoria) such as wheat leaf blotch fungi (Septoria tritici) genus; grape Botrytis, citrus Botrytis cinerea, cucumber Botrytis cinerea, tomato Botrytis cinerea , Strawberry gray mold fungus, eggplant gray mold fungus, kidney gray mold fungus, adzuki gray mold fungus, pea gray mold fungus, pea gray mold fungus, red pepper gray mold fungus, pepper gray mold fungus, lettuce gray mold fungus, onion gray mold fungus , Stachys gray mold, carnation gray mold, rose gray mold, pansy gray mold or sunflower gray mold, various gray molds ( Botrytis cinerea ), onion gray rot fungus ( Botrytis allii ), onion Botrytis Pathogenic bacteria that cause leaf blight caused by fungi ( Botryti s squamosa, Botrytis byssoidea, Botrytis (Botrytis) genus such as Botrytis tulipae); Pyricularia (Pyricularia) genus such as Pyricularia oryzae (Pyricularia oryzae); sugar beet brown spot fungus (Cercospora beticola), oyster angle plaques fungus (Cercospora kakivola Sakosupora (Cercospora) species such as); cucumber anthracnose fungi (Colletotrichum (Colletotrichum) genera such as Colletotrichum orbiculare); apple leaf spot fungus (Alternaria alternata apple pathotype), pear black spot fungus (Alternaria alternata Japanese pear pathotype), potato summer disease or tomato Wamon fungus (Alternaria solani), cabbage or Chinese cabbage black spot fungus (Alternaria brassicae), cabbage black soot fungus (Alternaria brassicola), onion or Welsh onion black spot fungus (Alternaria porri), such as Alternaria (Alternaria) Genus; Wheat eye rot fungus ( Pseudocercosporella Shu de circo sports these as herpotrichoides) (Pseudocercosporella) genus; grape brown spot oxalic de Sir Kos Paula, such as fungi (Pseudocercospora vitis) (Pseudocercospora) genus; Lincomycin spot tumefaciens, such as barley scald pathogen (Rhynchosporium secalis) (Rhynchosporium) genus; Gros, such as persimmon anthracnose fungus (Gloeosporium kaki); Cladosporium, such as peach scab (Cladosporium carpophilum) (Cladosporium) genus; Homopushisu (Phomopsis), such as Momohomopushisu corruption fungus belonging to the genus (Phomopsis sp.) Eosuporiumu (Gloeosporium) genus; Fulvia (Fulvia) genus, such as tomato leaf mold fungus (Fulvia fulva); Korinesupora (Corynespora) genus, and the like, such as cucumber brown spot pathogen (Corynespora cassiicola).

  Since the composition of the present invention can control various harmful fungi described above, it can control various diseases preventively or therapeutically. In particular, the composition of the present invention has various diseases that are problematic in the field of agriculture and horticulture, such as rice blast, sesame leaf blight, leaf blight or seedling blight; wheat powdery mildew, red mold, red rust Yellow rust, net blotch disease, leafy spot disease, snow rot, naked ear disease, eye spot disease, cloud shape disease, leaf blight or dry blight; citrus sunspot or scab; apple moniliosis, Powdery mildew, black spot disease, spotted leaf disease or black spot disease; pear black star disease or black spot disease; peach baldness, black star disease or fomopsis rot; grape black disease, late rot, brown spot disease, Branch rot, powdery mildew or downy mildew; anthracnose of oysters, deciduous lobster or horn spot disease; anthracnose of cucurbits, powdery mildew, vine blight, brown spot or downy mildew; tomato Ring rot, gray plague, leaf mold or plague; banana black sigatoka disease; sugar beet brown spot; pea brown spot; cruciferous vegetable black Effective for the control of various diseases such as potato plague or summer plague; strawberry powdery mildew or snake eye disease; beans, vegetables, fruit trees, flower buds, gray mold or mycosis Yes, among others, gray mold or fungus such as cucumber, green beans, azuki bean, soybean, pea, peanut, tomato, strawberry, eggplant, pepper, pepper, lettuce, onion, grape, citrus, statice, carnation, rose, pansy, sunflower It is particularly effective for controlling nuclear diseases.

The composition of the present invention is also effective for preventive or therapeutic control of soil diseases caused by phytopathogenic fungi such as Fusarium, Psium, Rhizoctonia, Verticillium, and Plasmodiophora.
The composition of the present invention is also effective in controlling various harmful harmful fungi against drugs such as benzimidazole, strobilurin, dicarboximide, phenylamide, and ergosterol biosynthesis inhibitor.
Furthermore, since the composition of the present invention has excellent osmotic transfer properties, by applying a pest control agent containing the composition of the present invention to the soil, simultaneously with the control of pests in the soil, the foliage part It can also control harmful fungi.

  The composition of the present invention is usually prepared by mixing an acid amide derivative of the formula (I) or a salt thereof with various agricultural adjuvants, a powder, a granule, a granule wettable powder, a wettable powder, an aqueous suspension, Used in various forms such as oil suspensions, aqueous solvents, emulsions, solutions, pastes, aerosols, microdispersions, etc. It can be in any formulation form. Adjuvants used in the formulation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch, etc. Solvents such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N, N-dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, alcohol; Fatty acid salts, benzoates, alkylsulfosuccinates, dialkylsulfosuccinates, polycarboxylates, alkylsulfate esters, alkylsulfates, alkylarylsulfates, alkyldiglycol ether sulfates, alcohols Lucol sulfate, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate ester, alkyl aryl phosphate, 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 Salts, anionic surfactants such as naphthalene sulfonic acid formalin condensate and spreading agents; sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polyglycols Ride, 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, polyethylene glycol, poly Nonionic surfactants and spreading agents such as oxyethylene fatty acid ester, 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, camellia oil, palm oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil Rapeseed oil, linseed oil, tung oil, vegetable oils, and the like or a mineral oil such as liquid paraffin. 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. In addition to the above-mentioned adjuvants, it can be used by appropriately selecting from those known in the art. For example, a bulking agent, a thickening agent, an anti-settling agent, an antifreezing agent, a dispersion stabilizer, a phytotoxicity reduction. Various commonly used adjuvants such as agents and antifungal agents can also be used. The mixing ratio of the acid amide derivative of the formula (I) or a salt thereof and various adjuvants is 0.001: 99.999 to 95: 5, preferably 0.005: 99.995 to 90:10. 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.

  Application of the composition of the present invention cannot be defined unconditionally due to differences in weather conditions, formulation forms, target crops, application timing, application location, types and occurrences of harmful fungi, types and occurrences of diseases, etc. In the case of treatment, it can be applied at an active ingredient concentration of 0.1 to 10,000 ppm, preferably 1 to 2,000 ppm, and the appropriate amount of application is 0.1 to 50,000 g of the acid amide derivative of the formula (I) or a salt thereof per hectare. Desirably, it can be about 1 to 30,000 g. In the case of soil treatment, 10 to 100,000, preferably 200 to 20,000 g of the acid amide derivative of the formula (I) or a salt thereof is generally applied per hectare.

  Application of various preparations of the composition of the present invention, or dilutions thereof, is generally performed by application methods such as spraying (eg spraying, spraying, misting, atomizing, dusting, water surface application, etc.), soil application. (Mixing, irrigation, etc.), surface application (application, powder coating, coating, etc.) can be performed. It can also be applied by the so-called ultra low volume application method (ultra low volume). In this method, it is possible to contain 100% of the active ingredient.

  The composition of the present invention can be mixed with or used in combination with other agricultural chemicals, fertilizers, safeners, etc. In this case, there are cases where more excellent effects and functions are exhibited. Other pesticides include herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. . In particular, the mixed bactericidal composition in which the acid amide derivative of the formula (I) or a salt thereof and one or more of the other bactericidal active ingredient compounds are used in combination or in combination is applicable range, timing of chemical treatment In some cases, the control activity is improved in a preferable direction. It should be noted that the acid amide derivative of formula (I) or a salt thereof and the active ingredient compound of other bactericides may be used separately by mixing them at the time of spraying. May be. The present invention also includes such a mixed bactericidal composition.

  The mixing ratio of the acid amide derivative of the formula (I) or a salt thereof and other active biocidal compound is the weather conditions, formulation form, target crop, application time, application place, type and occurrence of harmful fungi, disease Although it cannot be defined unconditionally due to differences in type and occurrence status, it can be generally 1: 300 to 300: 1, preferably 1: 100 to 100: 1. In addition, the appropriate amount of application can be 0.1 to 70,000 g, preferably 1 to 30,000 g as the total amount of active ingredient compounds per hectare. The present invention also includes a method for controlling harmful fungi by applying such a mixed bactericidal composition.

In the above-mentioned other pesticides, bactericidal active ingredient compounds (generic name; including partial application, or Japan Plant Protection Association test code) include, for example, mepanipyrim, pyrimethanil, cyprodinil ( Anilinopyrimidine compounds such as Cyprodinil;
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, Sipconazole, Prothioconazole, Triadimenol, Flutriafol, Difenoconazole ), Fluquinconazole, Fenbuconazole, Bromuconazole, Diniconazole, Tricyclazole, Probenazole, Simeconazole, Pefurazonate, Pefurazonate, Pefurazonate Azole compounds such as Ipconazole) and Imibenconazole;
Quinoxaline compounds such as quinomethionate;
Dithiocarbamate compounds such as Maneb, Zineb, Mancozeb, Polycarbamate, Metiram, Propineb;
Organochlorine compounds such as Fthalide, Chlorothalonil, Quintozene;
Imidazole compounds such as Benomyl, Thiophanate-Methyl, Carbendazim, Cyazofamid;
Cyanoacetamide compounds such as Cymoxanil;
Phenylamides such as Metalaxyl, Metalaxyl M, Oxadixyl, Offace, Benalaxyl, Benalaxyl M, Furalaxyl, Cyprofuram Compound;
Sulfenic acid compounds such as Dichlofluanid;
Copper-based compounds such as cupric hydroxide and organic copper (Oxine Copper);
Isoxazole compounds such as hymexazol;
Organic phosphorus systems such as fosetyl-aluminum, turfos-methyl-methyl, S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, aluminum ethyl hydrogen phosphonate Compound;
N-halogenothioalkyl compounds such as Captan, Captafol, Folpet;
Dicarboximide compounds such as Procymidone, Iprodione, Vinclozolin;
Benzanilide compounds such as Flutolanil, Mepronil, Zoxamid, Tiadinil;
Anilide compounds such as Boscalid;
Piperazine compounds such as Triforine;
Pyridine compounds such as Pyrifenox;
Carbinol compounds such as Fenarimol and Flutriafol;
Piperidine compounds such as Fenpropidine;
Morpholine compounds such as Fenpropimorph and Tridemorph;
Organotin compounds such as Fentin Hydroxide and Fentin Acetate;
Urea compounds such as Pencycuron;
Synamic acid compounds such as Dimethomorph and Flumorph;
Phenyl carbamate compounds such as Dietofencarb;
Cyanopyrrole compounds such as fludioxonil and fenpiclonil;
Azoxystrobin, Kresoxim-Methyl, Metominofen, Trifloxystrobin, Picoxystrobin, Oryzastrobin, Dimoxystrobin Strobilurin-based compounds such as Pyraclostrobin, Fluoxastrobin, and Fluacrypyrin;
Oxazolidinone compounds such as Famoxadone;
Thiazole carboxamide compounds such as ethaboxam;
Silylamide compounds such as Silthiopham;
Amino acid amide carbamate compounds such as Iprovalicarb, benchthiavalicarb-isopropyl;
An imidazolidine-based compound such as fenamidone;
Hydroxyanilide compounds such as Fenhexamid;
Benzenesulfonamide compounds such as Flusulfamide;
Oxime ether compounds such as cyflufenamid;
Phenoxyamide-based compounds such as phenoxanil;
Antibiotics such as polyoxins;
Guanidine-based compounds such as iminoctadine;
Other compounds include Isoprothiolane, Pyroquilon, Diclomezine, Quinoxyfen, Propamocarb Hydrochloride, Spiroxamine, Chloropicrin, and Dazomet (D). Sodium salt (Metam-sodium), Nicobifen, Metrafenone, MTF-753 (Pentiopyrad), UBF-307, Diclocymet, Proquinazid, NC-224 (Amibromdole, Amisulbrom) , KIF-7767 (KUF-1204, Pyribencarb methyl, Mepyricarb), Syngenta 446510 (Mandipropamid, Dipromandamid) and the like.

Examples of the active ingredient compounds (generic name; including some pending applications) of insecticides, acaricides, nematicides or soil pesticides in the above other pesticides include, for example, Profenofos, Dichlorvos ), Fenamiphos, Fenitrothion, EPN, Diazinon, Chlorpyrifos-methyl, Acephate, Prothiofos, Fosthiazate, Phosphocarb, usa ), Disulfoton, Chlorpyrifos, Demeton-S-methyl, dimethoate, methamidophos, etc .;
Carbaryl (Carbaryl), Propoxur, Aldicarb, Carbofuran, Thiodicarb, Methomyl, Oxamyl, Ethiofencarb, Pirimicarb, Fenocarb Carbamate compounds such as Carbosulfan and Benfuracarb;
Nereistoxin derivatives such as Cartap, Thiocyclam, Bensultap;
Organochlorine compounds such as Dicofol and Tetradifon;
Organometallic compounds such as Fenbutatin Oxide;
Fenvalerate, Permethrin, Cypermethrin, Deltamethrin, Cyhalothrin, Tefluthrin, Etofenprox, Fenpropathrin, Bifthrin Pyrethroid compounds such as
Benzoylurea compounds such as diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron, novaluron;
Juvenile hormone-like compounds such as Methoprene, Pyriproxyfen, Fenoxycarb;
Pyridazinone compounds such as Pyridaben;
Fenpyroximate, Fipronil, Tebufenpyrad, Ethiprole, Tolfenpyrad, Acetoprole, Pyrafluprole, Pyriprole, Pyriprole compounds;
Neonicotinoids such as Imidacloprid, Nitenpyram, Acetamiprid, Thiacloprid, Thiamethoxam, Clothianidin, Dinotefuran;
Hydrazine compounds such as Tebufenozide, Methoxyfenozide, Chromafenozide;
Dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazone compounds, and other compounds such as flonicamid, Buprofezin, Hexythiazox, Amitraz, Chlorimeform , Silafluofen, Triazamate, Pymetrozine, Pyrimidifen, Chlorfenapyr, Indoxacarb, Acequinocyl, Etoxazine, Etoxazole, Etoxazole 3-dichloropropene (1,3-dichloropropene), diafenthiuron (Benclothiaz), flufenerim (Flufenerim), pyridalyl (Pyridalyl), spirodiclofen (Spirodiclofen) , Bifenazate, Spiromesifen, Spirotetramat, Propargite, Clofentezine, Fluacrypyrim, Metaflumizone, Flubendiamide (Flubendiamide) A compound such as Cyflumetofen). Furthermore, microbial agents such as BT agents, entomopathogenic virus agents, entomopathogenic fungi agents, nematode pathogenic fungi agents, avermectin, emamectin benzoate, milbemectin, spinosad ( Spinosad), Ivermectin, Lepimectin and other antibiotics, and Azadirachtin natural products.

Preferred embodiments of the present invention are as follows. However, the present invention is not limited to these.
(1) An acid amide derivative represented by the formula (I) or a salt thereof.
(2) In the formula (I), A is phenyl which may be substituted with X, naphthyl which may be substituted with X, heterocyclic ring which may be substituted with X, or condensed heterocyclic ring which may be substituted with X B is a heterocycle optionally substituted with Y (excluding pyridyl), a fused heterocycle optionally substituted with Y, or naphthyl optionally substituted with Y; X is halogen, alkyl ( Alkyl may be substituted with halogen, hydroxy, alkoxy, haloalkoxy, alkylthio, alkylsulfonyl, cycloalkyl, amino, monoalkylamino, dialkylamino, cyano, alkoxycarbonyl or alkylcarbonyloxy), alkenyl, haloalkenyl, Alkynyl (Alkynyl is halogen, hydroxy, alkoxy, amino, hydroxycarbonyl, alkoxy Optionally substituted with carbonyl or trialkylsilyl), hydroxy, cyanooxy, alkoxy (alkoxy is substituted with halogen, alkoxy, haloalkoxy, alkylthio, cycloalkyl, monoalkylamino, dialkylamino, cyano or heterocycle. Alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio (alkylthio may be substituted with halogen, cycloalkyl or cyano), alkenylthio, haloalkenylthio, alkynylthio, haloalkynylthio, Alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cycloalkyl optionally substituted with halogen, cycloalkyloxy optionally substituted with halogen Optionally substituted with halogen, cycloalkylthio, cyano, nitro, formyl, phenyl (phenyl may be substituted with halogen, alkyl, haloalkyl or alkoxy), phenoxy optionally substituted with alkyl, substituted with alkyl Optionally substituted phenylthio, optionally substituted phenylalkyl, optionally substituted phenylalkenyl, optionally substituted phenylalkynyl, optionally substituted phenylalkyloxy, substituted by alkyl Phenylalkenyloxy which may be substituted, phenylalkynyloxy which may be substituted with alkyl, phenylamino which may be substituted with alkyl, —OR ⁴ , —SR ⁵ , —NR ⁶ R ⁷ , —CO ₂ R ⁸ , —C ^{(= O) NR 8 R 9} , -SO 2 NR 8 R 9, -CH = N ¹⁰ or heterocycle (heterocyclic ring, halogen, optionally substituted with alkyl or alkylcarbonyl may) be; Y is halogen, alkyl (alkyl, halogen, alkoxy, haloalkoxy, amino, monoalkylamino or dialkylamino May be substituted), alkenyl, alkynyl, hydroxy, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cycloalkyl, cyano, nitro, formyl, —OR ⁴ , —NR ⁶ R ⁷ , —CO ₂ R ⁸ , —C (═O) NR ⁸ R ⁹ , —SO ₂ NR ⁸ R ⁹ , —CH═NR ¹⁰ ; R ¹ and R ² are each independently a hydrogen atom, alkyl , Haloalkyl, alkoxyalkyl, alkenyl, alkynyl or cyclo R ¹ and R ² may be combined to form a 3- to 6-membered saturated carbocycle; R ³ is a hydrogen atom, alkyl (alkyl is halogen, alkoxy, haloalkoxy, alkylthio, amino , May be substituted with monoalkylamino, dialkylamino or cyano), alkenyl, alkynyl, hydroxy, alkoxy, haloalkoxy, cycloalkyl, cycloalkyloxy, cyano, formyl, —C (═W ³ ) R ¹¹ , — An acid amide derivative or a salt thereof which is C (= W ³ ) OR ¹² or —S (O) mR ¹² .

(3) A is phenyl optionally substituted with X, naphthyl optionally substituted with X, a heterocyclic ring optionally substituted with X, or a condensed heterocyclic ring optionally substituted with X; B is Y An optionally substituted 5-membered heterocycle, pyrazinyl or a fused heterocycle optionally substituted with Y; X is halogen, alkyl, haloalkyl, alkoxyalkyl, dialkylaminoalkyl, alkynyl, trialkylsilylalkynyl, hydroxy, alkoxy , Haloalkoxy, alkoxyalkoxy, cycloalkyl, nitro, phenyl, phenylalkynyl, pyridyloxy, alkylcarbonyloxy, alkylsulfonyloxy or heterocycle optionally substituted with haloalkyl (heterocycle is substituted with halogen, alkyl or alkylcarbonyl) Y is halogen Alkyl, haloalkyl, alkoxy, haloalkoxy cycloalkyl, or formyl; R ¹ and R ² each are independently a hydrogen atom or alkyl; R ³ is hydrogen, alkyl, alkylcarbonyl or alkoxycarbonyl; W ¹ And an acid amide derivative or a salt thereof, wherein W ² and each independently represent an oxygen atom or a sulfur atom.
(4) The acid amide derivative of (3) or a salt thereof, wherein both W ¹ and W ² are oxygen atoms.
(5) The acid amide derivative of the above (3) or a salt thereof, wherein B is a condensed heterocyclic ring optionally substituted with Y.

(6) The acid amide derivative according to (5) or a salt thereof, wherein the condensed heterocyclic ring is benzofuranyl, dihydrobenzofuranyl, benzodioxanyl or quinolyl.
(7) B is a 5-membered heterocyclic ring optionally substituted with Y; X is substituted with halogen, alkyl, haloalkyl, alkynyl, hydroxy, alkoxy, haloalkoxy, alkoxyalkoxy, cycloalkyl, nitro, phenylalkyl, haloalkyl which may be pyridyloxy, alkylcarbonyloxy, or heterocyclic ring (the heterocyclic is halogen, optionally substituted with alkyl or alkylcarbonyl may) be; Y is halogen, alkyl, haloalkyl or alkoxy; R ³ is hydrogen The acid amide derivative of (3) or a salt thereof, which is an atom, alkylcarbonyl or alkoxycarbonyl; and W ¹ and W ² are both oxygen atoms.
(8) B is furyl optionally substituted with Y, thienyl optionally substituted with Y, pyrrolyl optionally substituted with Y, oxazolyl optionally substituted with Y, isoxazolyl optionally substituted with Y, The acid amide derivative of the above (3) or (7), which is thiazolyl optionally substituted with Y, isothiazolyl optionally substituted with Y, pyrazolyl optionally substituted with Y or thiadiazolyl optionally substituted with Y Its salt.
(9) B is furyl optionally substituted with Y, thienyl optionally substituted with Y, pyrrolyl optionally substituted with Y, oxazolyl optionally substituted with Y, thiazolyl optionally substituted with Y, The acid amide derivative of (8) or a salt thereof, which is isothiazolyl optionally substituted with Y, pyrazolyl optionally substituted with Y, or thiadiazolyl optionally substituted with Y.
(10) The acid amide derivative of (9) or a salt thereof, wherein B is furyl substituted with Y.
(11) The acid amide derivative of (9) or a salt thereof, wherein B is thienyl substituted with Y.
(12) The acid amide derivative of (9) or a salt thereof, wherein B is pyrazolyl substituted with Y.

(13) An acid amide derivative represented by the formula (I-α) or a salt thereof.
(14) In the formula (I-α), B is a 5-membered heterocyclic ring optionally substituted with Y, pyrazinyl or a condensed heterocyclic ring optionally substituted with Y; ^Xα is a fluorine atom, a chlorine atom, Pyridyloxy optionally substituted with iodine atom, alkyl, haloalkyl, alkoxyalkyl, dialkylaminoalkyl, alkynyl, trialkylsilylalkynyl, hydroxy, alkoxy, haloalkoxy, alkoxyalkoxy, cycloalkyl, nitro, phenyl, phenylalkynyl, haloalkyl , Alkylcarbonyloxy, alkylsulfonyloxy or heterocycle (the heterocycle may be substituted with halogen, alkyl or alkylcarbonyl); Y is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl or formyl Yes; R ¹及R ² is each independently a hydrogen atom or alkyl; R ³ is a hydrogen atom, an alkyl, alkylcarbonyl or alkoxycarbonyl; W ¹ and W ² are each acid amide derivative is an oxygen atom or a sulfur atom independently or salt.
(15) The acid amide derivative or a salt thereof according to (14), wherein W ¹ and W ² are both oxygen atoms.
(16) The acid amide derivative of the above (14) or a salt thereof, wherein B is a condensed heterocyclic ring optionally substituted with Y.
(17) The acid amide derivative according to the above (16) or a salt thereof, wherein the condensed heterocyclic ring is benzofuranyl, dihydrobenzofuranyl, benzodioxanyl or quinolyl.

(18) B is a 5-membered heterocyclic ring optionally substituted with Y; ^Xα is a fluorine atom, chlorine atom, iodine atom, alkyl, haloalkyl, alkynyl, hydroxy, alkoxy, haloalkoxy, alkoxyalkoxy, cycloalkyl, Nitro, phenylalkynyl, pyridyloxy, alkylcarbonyloxy or heterocycle optionally substituted with haloalkyl (the heterocycle may be substituted with halogen, alkyl or alkylcarbonyl); Y is halogen, alkyl, haloalkyl or The acid amide derivative or a salt thereof according to (14), wherein R ³ is a hydrogen atom, alkylcarbonyl or alkoxycarbonyl; and W ¹ and W ² are both oxygen atoms.
(19) B is furyl optionally substituted with Y, thienyl optionally substituted with Y, pyrrolyl optionally substituted with Y, oxazolyl optionally substituted with Y, isoxazolyl optionally substituted with Y, Said (14) which is thiazolyl optionally substituted with Y, isothiazolyl optionally substituted with Y, imidazolyl optionally substituted with Y, pyrazolyl optionally substituted with Y or thiadiazolyl optionally substituted with Y Or an acid amide derivative of (18) or a salt thereof.
(20) B furyl optionally substituted with Y, thienyl optionally substituted with Y, pyrrolyl optionally substituted with Y, oxazolyl optionally substituted with Y, isoxazolyl optionally substituted with Y, The acid amide derivative according to (19) or a salt thereof, which is thiazolyl optionally substituted with Y, isothiazolyl optionally substituted with Y, pyrazolyl optionally substituted with Y, or thiadiazolyl optionally substituted with Y.
(21) The acid amide derivative according to (20) or a salt thereof, wherein B is furyl substituted with Y.
(22) The acid amide derivative of (20) or a salt thereof, wherein B is thienyl substituted with Y.
(23) The acid amide derivative of the above (20) or a salt thereof, wherein B is pyrazolyl substituted with Y.

(24) A is phenyl optionally substituted with X, naphthyl optionally substituted with X, benzodioxolanyl optionally substituted with X, or benzodioxanyl optionally substituted with X; B Is furyl optionally substituted with Y, thienyl optionally substituted with Y or pyrazolyl optionally substituted with Y; X is halogen, alkyl, haloalkyl, alkoxy or haloalkoxy; Y is halogen, alkyl , Haloalkyl, alkoxy or haloalkoxy; R ³ is a hydrogen atom; and W ¹ and W ² are both oxygen atoms, the acid amide derivative of (3) or (14) or a salt thereof.
(25) The acid amide derivative or the salt thereof according to (24), wherein B is furyl substituted with Y, thienyl substituted with Y, or pyrazolyl substituted with Y.
(26) The acid amide derivative or a salt thereof according to (24), wherein B is furyl substituted with Y, thienyl substituted with Y, or pyrazolyl substituted with Y, and Y is halogen, alkyl or haloalkyl.
(27) A is phenyl substituted with X or benzodioxolanyl substituted with X, and B is furyl substituted with Y, thienyl substituted with Y, or pyrazolyl substituted with Y 24) Acid amide derivatives or salts thereof.
(28) A is phenyl substituted with X or benzodioxolanyl substituted with X, B is furyl substituted with Y, thienyl substituted with Y, or pyrazolyl substituted with Y; The acid amide derivative or a salt thereof according to (24), wherein is halogen, alkyl or alkoxy, and Y is halogen, alkyl or haloalkyl.
(29) A is phenyl substituted with X or benzodioxolanyl substituted with X, B is furyl substituted with Y, thienyl substituted with Y, or pyrazolyl substituted with Y; The acid amide derivative according to (24) or a salt thereof, wherein ₁ and R ₂ are each alkyl, X is halogen, alkyl or alkoxy, and Y is halogen, alkyl or haloalkyl.
(30) The acid amide derivative of the above (24) to (29) or a salt thereof, wherein B is furyl substituted with Y.
(31) The acid amide derivative of the above (24) to (29) or a salt thereof, wherein B is thienyl substituted with Y.
(32) The acid amide derivative of the above (24) to (29) or a salt thereof, wherein B is pyrazolyl substituted with Y.

(33) A bactericidal composition comprising the acid amide derivative of (1) to (32) or a salt thereof as an active ingredient.
(34) A mixed bactericidal composition comprising the acid amide derivative of (1) to (32) or a salt thereof and another bactericidal active ingredient compound as active ingredients.
(35) Other bactericidal active ingredient compounds include anilinopyrimidine compounds, pyridinamine compounds, azole compounds, quinoxaline compounds, dithiocarbamate compounds, organochlorine compounds, imidazole compounds, cyanoacetamide compounds, phenyl Amide compounds, sulfenic acid compounds, copper compounds, isoxazole compounds, organophosphorus compounds, N-halogenothioalkyl compounds, dicarboximide compounds, benzanilide compounds, anilide compounds, piperazine compounds, pyridine compounds Compound, carbinol compound, piperidine compound, morpholine compound, organotin compound, urea compound, cinnamic acid compound, phenyl carbamate compound, cyanopyrrole compound, strobilurin compound, oxy Zolizinone compounds, thiazole carboxamide compounds, silylamide compounds, amino acid amide carbamate compounds, imidazolidine compounds, hydroxyanilide compounds, benzenesulfonamide compounds, oxime ether compounds, phenoxyamide compounds, antibiotics, guanidines Compounds, isoprothiolane, pyroxylone, dichromedin, quinoxifene, propamocarb hydrochloride, spiroxamine, chlorpicrin, dazomet, metam sodium salt, nicobifen, metolaphenone, MTF-753, UBF-307, diclosimet, proquinazide, NC-224, KIF-7767 and The mixed bactericidal composition according to the above (34), which is at least one selected from the group consisting of Syngenta 446510.
(36) Other bactericidal active ingredient compounds are pyridinamine compounds, azole compounds, dithiocarbamate compounds, organochlorine compounds, imidazole compounds, copper compounds, dicarboximide compounds, anilide compounds, piperazine compounds Compound, pyridine compound, carbinol compound, phenyl carbamate compound, cyanopyrrole compound, strobilurin compound, hydroxyanilide compound, MTF-753 and KIF-7767 (35) The mixed bactericidal composition according to the above.

(37) Other bactericidal active ingredient compounds are fluazinam, triadimephone, viteltanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanyl, cyproconazole, tebuconazole, hexaconazole, ferconazole cis , Prochloraz, metconazole, epoxiconazole, tetraconazole, oxpoconazole fumarate, cypconazole, prothioconazole, triadimenol, flutriafol, difenoconazole, fluquinconazole, fenbuconazole, bromconazole, Diniconazole, Tricyclazole, Probenazole, Cimeconazole, Pephrazoate, Ipconazole, Imibenconazole, Manneb, Dineb, Manzeb, Polycarbame , Methylam, propineb, fusalide, chlorothalonil, quintozen, benomyl, thiophanate methyl, carbendazim, cyazofamide, cupric hydroxide, organocopper, procymidone, iprodione, vinclozolin, boscalid, dietofencarb, fludioxonil, fenpicronyl, azoxystrobin, cresoxime methyl The group consisting of metminophen, trifloxystrobin, picoxystrobin, orizastrobin, dimoxystrobin, pyraclostrobin, fluoxastrobin, fluacrylpyrim, phenhexamide, polyoxin, iminotazine, MTF-753 and KIF-7767 (6) The mixed bactericidal composition according to the above (36), which is at least one selected from the group consisting of
(38) A method for controlling harmful fungi by applying an effective amount of the acid amide derivative or salt thereof of (1) to (32).
(39) A method for controlling plant diseases by applying an effective amount of the acid amide derivatives or salts thereof of (1) to (32).
(40) A method for protecting crops by applying an effective amount of the acid amide derivative or salt thereof according to (1) to (32).
(41) A method for improving crop yield by applying an effective amount of the acid amide derivative or salt thereof of (1) to (32).

Next, examples of the present invention will be described, but the present invention is not limited thereto. First, synthesis examples of acid amide derivatives of the formula (I) or (I-α) or salts thereof will be described.
Synthesis example 1
Synthesis of N-[(3 ', 4'-dichloro-1,1-dimethyl) phenacyl] -2-methyl-3-furancarboxamide (Compound No.1-57 described later)
(1) A mixture of 10.0 g of 3,4-dichlorobenzoyl chloride, 9.31 g of ethyl 2-bromoisobutyrate and 90 ml of anhydrous ether was added dropwise to 3.12 g of zinc under a nitrogen atmosphere, followed by reaction for 15 hours under reflux. The reaction mixture was filtered through celite and the filtrate was washed with 20% sulfuric acid and then with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/19) to obtain 8.7 g of oily ethyl 2- (3 ′, 4′-dichlorobenzoyl) isobutyrate. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz)
1.11 (t, 3H), 1.52 (s, 6H), 4.14 (q, 2H), 7.48 (d, 1H), 7.63 (dd, 1H), 7.96 (d, 1H)

(2) A mixture of 8.7 g of ethyl 2- (3 ′, 4′-dichlorobenzoyl) isobutyrate, 14.2 ml of sulfuric acid, 14.2 ml of water and 40 ml of acetic acid was reacted under reflux for 15 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/19) to obtain 6.47 g of oily 3,4-dichloroisobutyrophenone. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz)
1.21 (d, 6H), 3.46 (m, 1H), 7.55 (d, 1H), 7.79 (dd, 1H), 8.02 (d, 1H)

(3) To a mixture of 6.47 g of 3,4-dichloroisobutyrophenone and 100 ml of tetrahydrofuran, 9.32 g of phenyltrimethylammonium tribromide was added and reacted at room temperature for 4 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain 6.39 g of oily α-bromo-3,4-dichloroisobutyrophenone. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 300MHz)
2.01 (s, 6H), 7.50 (d, 1H), 8.0 (dd, 1H), 8.20 (d, 1H)

(4) To a mixture of 6.39 g of α-bromo-3,4-dichloroisobutyrophenone and 60 ml of dimethyl sulfoxide, 2.8 g of sodium azide was added and reacted at 50 ° C. for 1 hour. The reaction mixture was poured into water, extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/9) to obtain 6.34 g of oily α-azido-3,4-dichloroisobutyrophenone. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 300MHz)
1.60 (s, 6H), 7.53 (d, 1H), 7.97 (dd, 1H), 8.20 (d, 1H)

  (5) To a mixture of 6.34 g of α-azido-3,4-dichloroisobutyrophenone, 90 ml of tetrahydrofuran and 3.2 ml of water, 7.74 g of triphenylphosphine was added and reacted at room temperature for 23 hours. The reaction mixture was concentrated under reduced pressure, and the residue was made weakly acidic by adding water and then hydrochloric acid, and then washed with ether. The aqueous layer was neutralized with aqueous sodium hydroxide solution and extracted with ether. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Ethyl acetate was added to the residue, hydrogen chloride gas was introduced under ice cooling, and the resulting solid was collected by filtration and dried to obtain 5.92 g of α-amino-3,4-dichloroisobutyrophenone hydrochloride.

(6) To a mixture of 0.3 g of α-amino-3,4-dichloroisobutyrophenone hydrochloride and 10 ml of tetrahydrofuran was added 0.31 g of triethylamine, and the mixture was stirred at room temperature for 5 hours, and the mixture was concentrated under reduced pressure. To a mixture of the obtained residue, 0.195 g of 2-methyl-3-furancarboxylic acid and 20 ml of dichloromethane was added dropwise a mixture of 0.29 g of N, N′-dicyclohexylcarbodiimide and 10 ml of dichloromethane under ice cooling, and then at room temperature for 15 hours. Reacted. The reaction mixture was filtered and the filtrate was diluted with dichloromethane and washed with aqueous potassium carbonate then water. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/9) to obtain 0.08 g of the desired product having a melting point of 175 to 178 ° C. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz)
1.71 (s, 6H), 2.43 (s, 3H), 6.28 (s, 1H), 6.44 (d, 1H), 7.26 (d, 1H), 7.44 (d, 1H), 7.84 (dd, 1H), 8.11 (d, 1H)

Synthesis example 2
Synthesis of N-[(3'-difluoromethoxy-1,1-dimethyl) phenacyl] -5-chloro-1,3-dimethyl-4-pyrazolecarboxamide (Compound No.1-72 described later)
(1) A Grignard reagent prepared using 0.75 g of magnesium, 4.46 g of 2-bromopropane and 24 ml of anhydrous ether was added dropwise to a mixture of 4.09 g of 3-difluoromethoxybenzonitrile and 20 ml of anhydrous ether. After completion of dropping, the reaction was allowed to proceed at room temperature for 27 hours. The reaction mixture was poured into ice water and made weakly acidic by adding 6N sulfuric acid, followed by stirring for 0.5 hour. The mixture was extracted with ether and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/19) to obtain 2.04 g of 3-difluoromethoxyisobutyrophenone. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 300MHz)
1.23 (d, 6H), 3.52 (m, 1H), 6.56 (t, 1H), 7.32 (dd, 1H), 7.48 (t, 1H), 7.70 (s, 1H), 7.80 (d, 1H)

  (2) To a mixture of 2.04 g of 3-difluoromethoxyisobutyrophenone and 30 ml of tetrahydrofuran, 3.58 g of phenyltrimethylammonium tribromide was added and reacted at room temperature for 2 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain 2.79 g of oily α-bromo-3-difluoromethoxyisobutyrophenone.

(3) 1.24 g of sodium azide was added to a mixture of 2.79 g of α-bromo-3-difluoromethoxyisobutyrophenone and 35 ml of dimethyl sulfoxide, and reacted at 50 ° C. for 1 hour. The reaction mixture was poured into water, extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/9) to obtain 2.21 g of oily α-azido-3-difluoromethoxyisobutyrophenone. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 300MHz)
1.61 (s, 6H), 6.56 (t, 1H), 7.34 (dd, 1H), 7.48 (t, 1H), 7.86 (s, 1H), 7.98 (d, 1H)

  (4) A mixture of 2.18 g of α-azido-3-difluoromethoxyisobutyrophenone, 35 ml of methanol and 0.109 g of 5% palladium carbon was reacted at room temperature for 1.5 hours in a hydrogen atmosphere. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. Ethyl acetate was added to the residue, and hydrogen chloride gas was introduced under ice cooling, followed by concentration under reduced pressure to obtain 1.76 g of α-amino-3-difluoromethoxyisobutyrophenone hydrochloride.

(5) To a mixture of 0.3 g of α-amino-3-difluoromethoxyisobutyrophenone hydrochloride and 10 ml of tetrahydrofuran was added 0.33 g of triethylamine, and 0.25 g of 5-chloro-1,3-dimethyl-4-pyrazolecarbonyl chloride and A mixture of 5 ml of tetrahydrofuran was added dropwise under ice cooling. After completion of dropping, the reaction was allowed to proceed at room temperature for 3 hours. The reaction mixture was extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/4) to obtain 0.23 g of the desired product having a melting point of 138-139 ° C. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz)
1.75 (s, 6H), 2.28 (s, 3H), 3.80 (s, 3H), 6.50 (t, 1H), 6.80 (s, 1H), 7.23 (dd, 1H), 7.38 (t, 1H), 7.84 (s, 1H), 7.86 (d, 1H)

Synthesis example 3
Synthesis of N- [2- (2'-naphthylcarbonyl) -2-propyl] -5-chloro-1,3-dimethyl-4-pyrazolecarboxamide (Compound No. 2-1)
(1) To a mixture of 3.0 g of 2-naphthonitrile and 20 ml of anhydrous ether, a Grignard reagent prepared using 0.61 g of magnesium, 3.6 g of 2-bromopropane and 18 ml of anhydrous ether was added dropwise. After completion of the dropwise addition, the mixture was reacted for 12 hours under reflux. The reaction mixture was poured into ice water and made weakly acidic by adding 6N sulfuric acid, followed by stirring for 0.5 hour. The mixture was extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/50) to obtain 1.14 g of 2-naphthyl isopropyl ketone. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz)
1.27 (d, 6H), 3.73 (m, 1H), 7.53 to 7.65 (m, 2H), 7.86 to 7.92 (m, 2H), 7.97 (d, 1H), 8.03 (dd, 1H), 8.48 (d, 1H)

  (2) 2-Naphtyl 2.16 g of phenyltrimethylammonium tribromide was added to a mixture of 1.14 g of isopropyl ketone and 25 ml of tetrahydrofuran, and reacted at room temperature for 3 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain 1.59 g of oily α-bromoisopropyl 2-naphthyl ketone.

(3) α-bromoisopropyl 2-naphthylketone 0.75 g of sodium azide was added to a mixture of 1.59 g of 2-naphthylketone and 40 ml of dimethyl sulfoxide, and reacted at 50 ° C. for 1.5 hours. The reaction mixture was poured into water, extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/9) to obtain 1.19 g of oily α-azidoisopropyl 2-naphthyl ketone.
The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz)
1.68 (s, 1H), 7.54 to 7.66 (m, 2H), 7.86 to 7.90 (m, 2H), 7.98 (d, 1H), 8.10 (dd, 1H), 8.74 (d, 1H)

  (4) A mixture of α-azidoisopropyl 2-naphthyl ketone 0.3 g, methanol 10 ml and 5% palladium carbon 15 mg was reacted at room temperature for 1 hour in a hydrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to obtain 0.26 g of oily α-aminoisopropyl 2-naphthyl ketone.

(5) To a mixture of α-aminoisopropyl 2-naphthylketone 0.26 g and tetrahydrofuran 10 ml, triethylamine 0.19 g was added, and then a mixture of 5-chloro-1,3-dimethyl-4-pyrazolecarbonyl chloride 0.24 g and tetrahydrofuran 5 ml. Was added dropwise under ice-cooling. After completion of dropping, the reaction was allowed to proceed at room temperature for 15 hours. The reaction mixture was extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 2/3) to obtain 0.15 g of the desired product having a melting point of 145 to 147 ° C. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 300MHz)
1.87 (s, 6H), 2.28 (s, 3H), 3.79 (s, 3H), 7.05 (s, 1H), 7.48-7.58 (m, 2H), 7.80-7.90 (m, 3H), 8.05 (dd, 1H), 8.56 (d, 1H)

Synthesis example 4
N- [2-[(2 ′, 2 ′, 3 ′, 3′-tetrafluoro-1 ′, 4′-benzodioxan-6′-yl) carbonyl] isopropyl] -3-methyl-2-thiophenecarboxamide ( Synthesis of compound No. 4-10)
(1) To a mixture of 6-bromo-2,2,3,3-tetrafluoro-1,4-benzodioxane (3.0 g) and diethyl ether (38 ml) was added n-butyllithium (1.57 M) at −50 ° C. in a nitrogen atmosphere. n-Hexane solution) (7.3 ml) was added dropwise, and the mixture was stirred at the same temperature for 30 minutes. Thereto, 0.83 g of isobutyraldehyde was added dropwise at −70 ° C. or lower, and then the temperature was raised to room temperature and reacted for 15 hours. The reaction mixture was poured into water, made weakly acidic with hydrochloric acid and extracted with diethyl ether. The organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/9) to give oily 1- (2 ′, 2 ′, 3 ′, 3′-tetrafluoro-1 ′, 4 1.8 g of '-benzodioxan-6'-yl) -2-methylpropanol was obtained. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz)
0.83 (d, 3H), 0.96 (d, 3H), 1.92 (m, 1H), 4.40 (d, 1H), 6.90 (d, 1H), 7.10 (s, 2H), 7.14 (s, 1H)

(2) To a mixture of 2.08 g of pyridinium chlorochromate, 1.05 g of sodium acetate and 20 ml of dichloromethane, 1- (2 ′, 2 ′, 3 ′, 3′-tetrafluoro-1 ′, 4′-benzodioxan-6 ′ A mixture of 1.8 g of (yl) -2-methylpropanol and 7 ml of dichloromethane was added and reacted at room temperature for 2 hours. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/19) to give oily 2,2,3,3-tetrafluoro-1,4-benzodioxan-6-yl isopropyl 1.40 g of ketone was obtained. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz)
1.23 (d, 6H), 3.48 (m, 1H), 7.24 (d, 1H), 7.78 (d, 1H), 7.81 (dd, 1H)

  (3) To a mixture of 1.40 g of 2,2,3,3-tetrafluoro-1,4-benzodioxan-6-yl isopropyl ketone and 19.7 ml of tetrahydrofuran, add 1.89 g of phenyltrimethylammonium tribromide, and at room temperature for 2 hours Reacted. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain 1.78 g of oily α-bromoisopropyl 2,2,3,3-tetrafluoro-1,4-benzodioxan-6-yl ketone.

(4) To a mixture of α-bromoisopropyl 2,2,3,3-tetrafluoro-1,4-benzodioxan-6-yl ketone 1.78 g and dimethyl sulfoxide 10 ml, 0.65 g of sodium azide was added, and The reaction was performed for 2 hours. The reaction mixture was poured into water, extracted with diethyl ether and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/19) to give oily α-azidoisopropyl 2,2,3,3-tetrafluoro-1,4-benzodioxane- 1.5 g of 6-yl ketone was obtained. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz)
1.61 (s, 6H), 7.23 (d, 1H), 8.01 to 8.03 (m, 2H)

  (5) A mixture of α-azidoisopropyl 2,2,3,3-tetrafluoro-1,4-benzodioxan-6-yl ketone 0.25 g, methanol 15 ml and 5% palladium carbon 13 mg at room temperature under a hydrogen atmosphere. Reacted for 1 hour. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to obtain 0.23 g of oily α-aminoisopropyl 2,2,3,3-tetrafluoro-1,4-benzodioxan-6-yl ketone.

(6) α-aminoisopropyl 2,2,3,3-tetrafluoro-1,4-benzodioxan-6-yl To a mixture of 0.23 g of ketone and 10 ml of tetrahydrofuran, 0.16 g of triethylamine was added, and 3-methyl- A mixture of 0.13 g of 2-thiophenecarbonyl chloride and 5 ml of tetrahydrofuran was added dropwise under ice cooling, and the mixture was reacted at room temperature for 3 hours. The reaction mixture was extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/4) to obtain 0.23 g of the desired product having a melting point of 120 to 122 ° C. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 300MHz)
1.76 (s, 6H), 2.39 (s, 3H), 6.54 (s, 1H), 6.84 (d, 1H), 7.24 (d, 1H), 7.42 (d, 1H), 7.84 (s, 1H), 7.96 (s, 1H)

Synthesis example 5
Synthesis of N-[(3 ′, 4′-dichloro-1,1-dimethyl) phenacyl] -3-methyl-2-thiophenecarboxamide (Compound No. 1-20 described later) Synthesis Example 1 (1) to (5 ) To a mixture of 268 mg of α-amino-3,4-dichloroisobutyrophenone hydrochloride obtained according to the method of (5) and 5 ml of tetrahydrofuran, add 303 mg of triethylamine, and then add 265 mg of 3-methyl-2-thiophenecarbonyl chloride and tetrahydrofuran. 2.5 ml of the mixture was added dropwise under ice cooling. After completion of dropping, the reaction was allowed to proceed at room temperature for 3 hours. The reaction mixture was extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/3) to obtain 180 mg of the desired product having a melting point of 141 ° C. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz)
1.72 (s, 6H), 2.37 (s, 3H), 6.53 (s, 1H), 6.85 (d, 1H), 7.25 (d, 1H), 7.43 (d, 1H), 7.86 (dd, 1H), 8.13 (s, 1H)

Synthesis Example 6
Synthesis of N-[(4'-methoxy-2'-methyl-1,1-dimethyl) phenacyl] -3-methyl-2-thiophenecarboxamide (Compound No. 1-160 described later)
(1) To a mixture of 7.15 g of aluminum chloride and 20 ml of carbon disulfide, a mixture of 5.7 g of isobutyryl chloride and 5 ml of carbon disulfide was added dropwise at 10 ° C. or less and reacted for 0.5 hours. Next, a mixture of 5.0 g of m-cresol and 5 ml of carbon disulfide was added dropwise at 5 ° C. or lower, and reacted at room temperature for 4 hours. The reaction mixture was poured into a mixture of ice water and hydrochloric acid, extracted with methylene chloride, and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the residue, 60 ml of tetrahydrofuran, 30 ml of water and 3.7 g of sodium hydroxide were added and reacted at room temperature for 1.5 hours. The reaction mixture was concentrated under reduced pressure, poured into ice water, made weakly acidic with dilute sulfuric acid, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/9) to obtain 2.45 g of solid 4-hydroxy-2-methylisobutyrophenone. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz)
1.15 (d, 6H), 2.43 (s, 3H), 3.40 (m, 1H), 6.70 (m, 2H), 7.57 (d, 1H)

(2) To a mixture of 0.8 g of 4-hydroxy-2-methylisobutyrophenone, 0.68 g of potassium carbonate and 15 ml of dimethylformamide, a mixture of 0.62 g of dimethyl sulfate and 3 ml of dimethylformamide was added and reacted at room temperature for 3 hours. The reaction mixture was poured into water, extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/9) to obtain 0.59 g of oily 4-methoxy-2-methylisobutyrophenone. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz)
1.13 (d, 6H), 2.46 (s, 1H), 3.38 (m, 1H), 6.72 (m, 2H), 7.59 (d, 1H)

  (3) To a mixture of 0.59 g of 4-methoxy-2-methylisobutyrophenone and 15 ml of tetrahydrofuran, 1.16 g of phenyltrimethylammonium tribromide was added and reacted at room temperature for 2.5 hours. Ether was added to the reaction mixture, insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure to obtain 0.7 g of oily α-bromo-4-methoxy-2-methylisobutyrophenone.

(4) To a mixture of 0.7 g of α-bromo-4-methoxy-2-methylisobutyrophenone and 8 ml of dimethyl sulfoxide, 0.4 g of sodium azide was added and reacted at 50 ° C. for 1.5 hours. The reaction mixture was poured into water, extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/9) to obtain 0.67 g of oily α-azido-4-methoxy-2-methylisobutyrophenone. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 300MHz)
1.54 (s, 6H), 2.33 (s, 1H), 3.81 (s, 3H), 6.72 (dd, 1H), 6.75 (d, 1H), 7.61 (d, 1H)

  (5) A mixture of 0.25 g of α-azido-4-methoxy-2-methylisobutyrophenone, 10 ml of methanol and 13 mg of 5% palladium carbon was reacted at room temperature for 3 hours in a hydrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to obtain 0.23 g of oily α-amino-4-methoxy-2-methylisobutyrophenone.

(6) 0.13 g of triethylamine was added to a mixture of 0.22 g of α-amino-4-methoxy-2-methylisobutyrophenone and 12 ml of tetrahydrofuran, and a mixture of 0.17 g of 3-methyl-2-thiophenecarbonyl chloride and 3 ml of tetrahydrofuran was added thereto. The solution was added dropwise under ice cooling. After completion of dropping, the reaction was allowed to proceed at room temperature for 2 hours. The reaction mixture was extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/3) to obtain 0.35 g of the desired product having a melting point of 99 to 101 ° C. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 300MHz)
1.77 (s, 6H), 2.38 (s, 3H), 2.45 (s, 3H), 6.81 (dd, 1H), 6.71 (s, 1H), 6.85 (m, 2H), 7.26 (d, 1H), 7.49 (d, 1H)

Synthesis example 7
Synthesis of N-[(3 ', 4'-dimethoxy-1,1-dimethyl) phenacyl] -3-methyl-2-thiophenecarboxamide (Compound No. 1-535 below)
(1) A solution of isopropylmagnesium bromide ether prepared from 5.6 g of 2-bromopropane, 0.94 g of magnesium and 30 ml of ether was added dropwise to a mixture of 5.0 g of 3,4-dimethoxybenzaldehyde and 50 ml of ether and reacted for 15 hours under reflux. . The reaction mixture was poured into ice water, diluted sulfuric acid was added and stirred, extracted with methylene chloride, and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 6.3 g of oily 1- (3 ′, 4′-dimethoxyphenyl) -2-methylpropanol.

(2) To a mixture of pyridinium chlorochromate 6.5 g, sodium acetate 4.9 g and dichloromethane 100 ml, add a mixture of 1- (3 ′, 4′-dimethoxyphenyl) -2-methylpropanol 6.28 g and dichloromethane 30 ml at room temperature. The reaction was allowed for 15 hours. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 3/7) to obtain 3.9 g of oily 3,4-dimethoxyisobutyrophenone. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz)
1.70 (d, 6H), 3.50 (m, 1H), 3.89 (s, 3H), 3.90 (s, 3H), 6.85 (d, 1H), 7.50 (d, 1H), 7.56 (dd, 1H)

  (3) To a mixture of 1.0 g of 3,4-dimethoxyisobutyrophenone and 20 ml of tetrahydrofuran, 1.81 g of phenyltrimethylammonium tribromide was added and reacted at room temperature for 2 hours. Ether was added to the reaction mixture, insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure to obtain oily α-bromo-3,4-dimethoxyisobutyrophenone.

(4) 0.62 g of sodium azide was added to a mixture of 20 ml of α-bromo-3,4-dimethoxyisobutyrophenone and dimethyl sulfoxide, and reacted at 50 ° C. for 1.5 hours. The reaction mixture was poured into water, extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/4) to obtain 1.1 g of oily α-azido-3,4-dimethoxyisobutyrophenone. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz)
1.56 (s, 6H), 3.91 (s, 3H), 3.93 (s, 3H), 6.86 (d, 1H), 7.62 (d, 1H), 7.94 (dd, 1H)

  (5) A mixture of 0.25 g of α-azido-3,4-dimethoxyisobutyrophenone, 15 ml of methanol and 13 mg of 5% palladium on carbon was reacted at room temperature for 3 hours in a hydrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to obtain 0.2 g of oily α-amino-3,4-dimethoxyisobutyrophenone.

(6) 0.11 g of triethylamine was added to a mixture of 0.2 g of α-amino-3,4-dimethoxyisobutyrophenone and 12 ml of 1,2-dichloroethane, and 0.14 g and 1,2 of 3-methyl-2-thiophenecarbonyl chloride were added thereto. -A mixture of 2 ml of dichloroethane was added dropwise under ice cooling. After completion of dropping, the reaction was allowed to proceed at room temperature for 1.5 hours. The reaction mixture was extracted with methylene chloride and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 3/2) to obtain 0.1 g of the desired product having a melting point of 138 to 140 ° C. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 300MHz)
1.82 (s, 6H), 2.44 (s, 3H), 3.89 (s, 6H), 6.80 (d, 1H), 6.85 (d, 1H), 6.88 (s, 1H), 7.23 (d, 1H), 7.63 (d, 1H), 7.75 (dd, 1H)

Next, typical examples of the acid amide derivative of the formula (I) or (I-α) or a salt thereof are specifically shown in Tables 1 to 9. These compounds can be synthesized based on the above synthesis examples or the various production methods described above.
In the table, No. indicates the compound No., Me is methyl, Et is ethyl, Pr (i) is isopropyl, Pr (n) is normal propyl, Bu (t) is tertiary butyl, and Bu (n) is normal. Butyl, Bu (sec) is secondary butyl, CO is carbonyl, CO ₂ is carboxyl, and Ph is phenyl. In the table, Ph (4-Cl) means phenyl substituted with a chlorine atom at the 4-position, and Ph (3,4-Cl ₂ ) means chlorine at the 3-position and 4-position, respectively. A phenyl substituted by an atom is shown, and other similar descriptions are based on these. In addition, the abbreviations D1 to D7 and B1 to B117 used in the table respectively represent the following substituents.

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

Test Example 1 (Wheat powdery mildew prevention effect test)
Growing wheat (variety: Norin 61) in a 7.5cm diameter plastic pot, and spraying 10ml of chemical solution with acid amide derivative of formula (I) or its salt adjusted to predetermined concentration when 1.5 leaf stage is reached Sprayed with a gun. After the chemical solution was dried (on the day of treatment), conidia of powdery mildew ( Erysiphe graminis ) were sprinkled and inoculated, and kept in a constant temperature room at 20 ° C. The spore formation area was investigated 6 to 7 days after the inoculation, and the control index was determined according to the above evaluation criteria. Compound No. 1-13, 1-29, 1-39, 1-54, 1-90, 1-96, 1-100, 1-101, 1-106, 1-107, 1-109, 1- 124, 1-125, 1-127, 1-148, 1-152, 1-156, 1-174, 1-175, 1-190, 1-205, 1-516, 3-4, 3-9, When tested for 3-10, 3-12, 3-19, 3-20, 4-19, 6-1 or 7-2, all compounds showed an effect with a control index of 4 or 5 at 500 ppm.

Test Example 2 (Cucumber powdery mildew prevention effect test)
Cucumber (variety: Sagamihanjiro) is cultivated in a 7.5cm diameter plastic pot, and when 1.5 leaf stage is reached, spray 10ml of chemical solution adjusted to the prescribed concentration of acid amide derivative of formula (I) or its salt Sprayed with a gun. After the drug solution was dried (on the day of treatment or the next day), a conidial spore suspension of powdery mildew ( Sphaerotheca fuliginea ) was spray-inoculated and kept in a constant temperature room at 20 ° C. The spore formation area was investigated 6 to 7 days after the inoculation, and the control index was determined according to the above evaluation criteria. Compound Nos. 1-6, 1-9, 1-11, 1-14, 1-15, 1-17 to 1-22, 1-27 to 1-29, 1-32, 1-33, 1- 36, 1-39, 1-41 to 1-43, 1-47, 1-53 to 1-56, 1-62 to 1-64, 1-66, 1-73, 1-77, 1-79, 1-90, 1-93, 1-97 to 1-104, 1-106 to 1-108, 1-111, 1-115, 1-119, 1-120, 1-124, 1-127, 1- 129, 1-131, 1-148, 1-150, 1-152, 1-156, 1-160, 1-161, 1-164, 1-165, 1-167, 1-170, 1-172, 1-174, 1-175, 1-190, 1-205, 1-516, 2-1, 2-14, 3-2, 3-4, 3-6, 3-9, 3-10, 3- When tested for 12, 3-19, 3-20, 3-23, 4-10 or 6-1 to 6-3, all the compounds showed an effect of controlling index 4 or 5 at 500 ppm. When tested for 1-34, an effect of control index 4 was shown at 200 ppm.

Test example 3 (rice blast prevention effect test)
Rice (variety: Nipponbare) is cultivated in a 7.5 cm diameter plastic pot, and when the 1.5 leaf stage is reached, 10 ml of a chemical solution prepared by adjusting the acid amide derivative of formula (I) or a salt thereof to a predetermined concentration is applied to a spray gun. And sprayed. After the chemical solution is dried (on the day of treatment or the next day), a conidial spore suspension of blast fungus ( Pyricularia oryzae ) is spray-inoculated and kept in a 20 ° C. inoculation box for 24 hours, and then kept in a constant temperature room at 20 ° C. . The number of lesions was investigated 5 to 7 days after the inoculation, and the control index was determined according to the evaluation criteria. Compound Nos. 1-6, 1-9, 1-13, 1-14, 1-28, 1-45, 1-47, 1-52, 1-53, 1-55, 1-56, 1- 62, 1-63, 1-66, 1-75, 1-77, 1-79, 1-109, 1-119, 1-164, 2-1, 2-2, 3-25 or 4-19 When tested, all compounds showed an effect of control index 4 or 5 at 500 ppm.

Test Example 4 (Injury gray mold prevention effect test)
Growing green beans (variety: Taishokin) in a 15 cm diameter plastic pot, and when the true leaf is fully developed, spray 10 ml of a chemical solution adjusted to the prescribed concentration of the acid amide derivative of formula (I) or salt thereof with a spray gun. did. After the drug solution is dried (on the day of treatment or the next day), it is inoculated with a Botrytis cinerea spore suspension (potato / glucose broth diluted to 50% with water) and kept in a constant temperature room at 20 ° C. . The lesion length (mm) was examined 3 days after the inoculation, and the control index was determined according to the above evaluation criteria. Compound Nos. 1-11, 1-15, 1-17, 1-20, 1-22, 1-27, 1-41, 1-43, 1-52, 1-80, 1-99, 1- 102, 1-112 to 1-115, 1-117, 1-118, 1-120, 1-125, 1-131, 1-136, 1-160, 1-162, 1-169, 1-172, 1-176, 1-180, 1-182, 1-186-1-189, 1-273, 2-2, 2-9, 2-13, 2-14 or 7-6 The compound showed an effect of controlling index 4 or 5 at 500 ppm.

Test Example 5 (Test for preventing kidney bean nuclear disease)
Growing green beans (variety: Taishokin) in a 15 cm diameter plastic pot, and when the true leaf is fully developed, spray 10 ml of a chemical solution adjusted to the prescribed concentration of the acid amide derivative of formula (I) or salt thereof with a spray gun. did. After the chemical solution was dried (on the day of treatment or the next day), a flora disc of Sclerotinia sclerotiorum was inoculated and kept in a constant temperature room at 20 ° C. The lesion length (mm) was examined 3 days after the inoculation, and the control index was determined according to the above evaluation criteria. Compound Nos. 1-1, 1-4, 1-7, 1-10, 1-16, 1-18, 1-19, 1-21, 1-26, 1-30 to 1-33, 1- 36, 1-38, 1-42, 1-44, 1-46, 1-57, 1-60, 1-64, 1-69, 1-71, 1-73, 1-75, 1-80, 1-86, 1-93, 1-96 to 1-98, 1-103 to 1-105, 1-108, 1-111 to 1-114, 1-117, 1-118, 1-123, 1- 126, 1-128, 1-129, 1-133 to 1-136, 1-141 to 1-144, 1-146, 1-149, 1-150, 1-159, 1-161 to 1-163, 1-165 to 1-171, 1-176, 1-180, 1-181, 1-186, 1-188, 1-208, 1-209, 1-271, 1-273, 1-276, 1- 535, 2-1, 2-3, 2-4, 2-10, 2-11, 2-13, 3-2, 3-3, 3-6, 3-23, 3-26, 4-10, When 6-2, 6-3, 7-2, 7-4, 7-6 to 7-8 or 7-66 were tested, all compounds showed an effect of controlling index 4 or 5 at 500 ppm.

Test Example 6 (Wheat Blight Prevention Effect Test)
Growing wheat (variety: Norin 61) in a 7.5cm diameter plastic pot, and spraying 10ml of chemical solution with acid amide derivative of formula (I) or its salt adjusted to predetermined concentration when 1.5 leaf stage is reached Sprayed with a gun. To (the same day) After the chemical solution dried, conidia suspension of glume blotch fungus (Septoria nodorum) was sprayed and inoculated, maintaining inoculation box 72 hours 20 ° C., was maintained in a constant temperature chamber of subsequent 20 ° C.. The number of lesions was investigated 5 to 10 days after the inoculation, and the control index was determined according to the evaluation criteria. When tested for Compound No. 1-179 or 1-189, all compounds showed an effect of controlling index 4 or 5 at 500 ppm.

Test Example 7 (Rice blight prevention effect test)
Rice (variety: Nipponbare) is cultivated in a 7.5cm diameter plastic pot, and when the 5th leaf stage is reached, 10ml of chemical solution adjusted to the prescribed concentration of the acid amide derivative of formula (I) or its salt is sprayed with a spray gun. did. After the chemical solution was dried (on the day of treatment or the next day), a precultured bacterial flora ( Rhizoctonia solani ) flora disc was sandwiched between the leaf tops, fixed with a string, and kept in a 25 ° C. inoculation box. The lesion length was investigated 5 to 7 days after the inoculation, and the control index was determined according to the above evaluation criteria. When the compounds No. 1-130, 1-137 or 3-3 were tested, all compounds showed an effect of controlling index 4 or 5 at 500 ppm.

Next, although the formulation example of this invention composition is described, a mixture ratio, a dosage form, etc. are not limited only to a description example.
Formulation Example 1
(1) Compound of formula (I) 20 parts by weight (2) 72 parts by weight of clay (3) Sodium lignin sulfonate 8 parts by weight or more is uniformly mixed to obtain a wettable powder.
Formulation Example 2
(1) Compound of formula (I) 5 parts by weight (2) Talc 95 parts by weight or more is uniformly mixed to obtain a powder.
Formulation Example 3
(1) Compound of formula (I) 20 parts by weight (2) N, N'-dimethylacetamide 20 parts by weight (3) Polyoxyethylene alkylphenyl ether 10 parts by weight (4) Xylene 50 parts by weight or more uniformly Mix and dissolve to make emulsion.

Formulation Example 4
(1) Clay 68 parts by weight (2) Lignin sulfonic acid soda 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) Fine powder silica A mixture of 25 parts by weight or more of each component of formula (I) The compound is mixed at a weight ratio of 4: 1 to obtain a wettable powder.
Formulation Example 5
(1) 50 parts by weight of the compound of the formula (I) (2) Oxylated polyalkylphenyl phosphate-triethanolamine 2 parts by weight (3) 0.2 part by weight of silicone (4) 47.8 parts by weight or more of water (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are added to the stock solution that is uniformly mixed and pulverized. .
Formulation Example 6
(1) Compound of formula (I) 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) are mixed uniformly in advance and diluted with an appropriate amount of acetone, and then sprayed on (4) to remove the acetone and form granules.

Formulation Example 7
(1) Compound of formula (I) 2.5 parts by weight (2) N-methyl-2-pyrrolidone 2.5 parts by weight (3) Soybean oil 95.0 parts by weight Use as an ultra low volume formulation.
Formulation Example 8
(1) Compound of formula (I) 20 parts by weight (2) Oxidated polyalkylphenol phosphate-triethanolamine 2 parts by weight (3) Silicone 0.2 parts by weight (4) Xanthan gum 0.1 parts by weight (5) Ethylene glycol 5 parts by weight (6) Water 72.7 parts by weight or more are uniformly mixed and pulverized to obtain an aqueous suspension.

Claims (9)

Formula (I):

[Wherein A is phenyl optionally substituted with X, naphthyl optionally substituted with X, benzodioxolanyl optionally substituted with X, benzodioxanyl optionally substituted with X, or X Thienyl which may be substituted; B is furyl which may be substituted with Y, thienyl which may be substituted with Y or pyrazolyl which may be substituted with Y; X is halogen, alkyl, haloalkyl, alkoxyalkyl , Dialkylaminoalkyl, alkynyl, trialkylsilylalkynyl, hydroxy, alkoxy, haloalkoxy, alkoxyalkoxy, cycloalkyl, nitro, phenyl, phenylalkynyl, haloalkyl optionally substituted with pyridyloxy, alkylcarbonyloxy, alkylsulfonyloxy or Heterocycle (heterocycle is halogen, a Substituted with killed or alkylcarbonyl be also be); Y is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, or formyl; R ¹ and R ² are each are independently a hydrogen atom or alkyl; R ³ is a hydrogen atom, alkyl, alkylcarbonyl or alkoxycarbonyl; both W ¹ and W ² are oxygen atoms . However, the composition for sterilization which contains as an active ingredient the acid amide derivative or its salt represented by] except that R ¹ and R ² are hydrogen atoms at the same time .

A is phenyl optionally substituted with X, naphthyl optionally substituted with X, benzodioxolanyl optionally substituted with X, or benzodioxanyl optionally substituted with X ; R ¹ and R ² is each alkyl ; X is halogen, alkyl, haloalkyl, alkoxy or haloalkoxy; Y is halogen, alkyl, haloalkyl, alkoxy or haloalkoxy; R ³ is a hydrogen atom; W ¹ and W ² disinfecting composition according to claim 1 but are both oxygen atoms. Disinfecting composition according to claim 1 or 2 B is furyl substituted by Y. Disinfecting composition according to claim 1 or 2 B is thienyl substituted by Y. Disinfecting composition according to claim 1 or 2 B is pyrazolyl substituted with Y. A composition for mixed sterilization comprising the acid amide derivative of formula (I) or a salt thereof according to claim 1 and another sterilizing active ingredient compound as active ingredients. Other bactericidal active ingredient compounds are anilinopyrimidine compounds, pyridinamine compounds, azole compounds, quinoxaline compounds, dithiocarbamate compounds, organochlorine compounds, imidazole compounds, cyanoacetamide compounds, phenylamide compounds Sulfenic acid compounds, copper compounds, isoxazole compounds, organophosphorus compounds, N-halogenothioalkyl compounds, dicarboximide compounds, benzanilide compounds, anilide compounds, piperazine compounds, pyridine compounds, carbides Nord compound, piperidine compound, morpholine compound, organotin compound, urea compound, cinnamic acid compound, phenyl carbamate compound, cyanopyrrole compound, strobilurin compound, oxazolid Compounds, thiazolecarboxamide compounds, silylamide compounds, amino acid amide carbamate compounds, imidazolidine compounds, hydroxyanilide compounds, benzenesulfonamide compounds, oxime ether compounds, phenoxyamide compounds, antibiotics, guanidines Compounds, isoprothiolane, pyroxylone, dichromedin, quinoxifene, propamocarb hydrochloride, spiroxamine, chlorpicrin, dazomet, metam sodium salt, nicobifen, metolaphenone, MTF-753, UBF-307, diclosimet, proquinazide, NC-224, KIF-7767 and The composition for mixed sterilization according to claim 6 , wherein the composition is at least one selected from the group consisting of Syngenta 446510. A method for controlling harmful fungi by applying an effective amount of the acid amide derivative of the formula (I) or a salt thereof according to claim 1. A method for controlling plant diseases by applying an effective amount of the acid amide derivative of the formula (I) or a salt thereof according to claim 1.