Oxadiazoline compounds or salts thereof, agricultural and horticultural fungicides containing said compounds, and methods of using the same

Abstract

The development of novel agricultural and horticultural bactericides is desired as diseases still cause serious damage in agricultural and horticultural crop production, and because of outbreaks of diseases resistant to existing chemicals.　General formula (I) As a result of intensive studies carried out to develop a novel agricultural and horticultural bactericide, the present inventors have found that the compound represented by general formula (I) or salts thereof according to the present invention has a high bactericidal activity against pathogenic bacteria causing plant diseases that pose problems in the agricultural and horticultural field, and have achieved the present invention.

Description

[Technical field]

[0001] The present invention relates to an agricultural and horticultural fungicide containing an oxadiazoline compound or a salt thereof as an active ingredient, and a method for using the same. [Background technology]

[0002] Patent Documents 1 and 2 disclose that compounds having an oxadiazoline with a trifluoromethyl group in the structure have fungicidal activity against bacteria causing plant diseases. However, these documents do not specifically disclose compounds in which an oxadiazoline ring is bonded to a thiophene. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2019 / 171234 Brochure [Patent Document 2] International Publication No. 2019 / 197371 Brochure Summary of the Invention [Problem to be solved by the invention]

[0004] In agricultural and horticultural crop production, damage caused by diseases remains significant, and the development of new fungicides for agricultural and horticultural use is desired due to factors such as the emergence of diseases resistant to existing fungicides. [Means for solving the problem]

[0005] Means for Solving the Problems The present inventors have conducted extensive research to develop novel fungicides, and as a result have found that the compounds represented by the general formula (I) of the present invention or salts thereof are useful as agricultural and horticultural fungicides, thereby completing the present invention.

[0006] That is, the present invention is [1] General formula (I) [ka] where L is the following structural formula L 1 , L 2 Or L 3 The structure shown is either of the following: [ka] Q is, (a1) (C1-C6) alkyl group; (a2) (C2-C6) alkenyl group; (a3) (C2-C6) alkynyl group; (a4) (C3-C6) cycloalkyl group; (a5) a (C1-C6)alkoxy group; (a6) halo(C1-C6)alkyl group; (a7) halo(C2-C6)alkenyl group; (a8) halo(C2-C6)alkynyl group; (a9) halo(C3-C8)cycloalkyl group; (a10) a halo(C1-C6)alkoxy group; (a11) (C1-C6) alkylthio group; (a12) (C1-C6) alkylsulfinyl group; (a13) (C1-C6) alkylsulfonyl group; (a14) Halo(C1-C6)alkylthio group; (a15) a halo(C1-C6)alkylsulfinyl group; (a16) halo(C1-C6)alkylsulfonyl group; (a17) R 3 (R 4 )N group; (a18) an aryl group; (a19) each independently represents a halogen atom, a cyano group, a nitro group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, a halo(C1-C6)alkoxy group, a halo(C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylthio group, a halo(C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfonyl group, R 3 (R 4 )N group, (C1-C6)alkoxycarbonyl group and R 3 (R 4 ) a substituted aryl group having 1 to 8 substituents on the ring selected from the group consisting of N-carbonyl groups; (a20) a 5- to 6-membered heterocycle or an 8- to 10-membered fused heterocycle; (a21) each independently represents a halogen atom, a cyano group, a nitro group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, a halo(C1-C6)alkoxy group, a halo(C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylthio group, a halo(C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfonyl group, R 3 (R 4 )N group, (C1-C6)alkylthio(C1-C6)alkyl group, phenyl group, halogen-substituted phenoxy group, (C1-C6)alkoxycarbonyl group and R 3 (R 4 )N-carbonyl groups. R 1 and R 2 are each independently, (b1) a hydrogen atom; (b2) a halogen atom; (b3) (C1-C6) alkyl group; (b4) a halo(C1-C6)alkyl group; or (b5) represents a (C1-C6) alkoxy group. R 1 and R 2 may be taken together with the carbon atoms to which they are attached to form a cyclopropane ring. R 3 and R 4 are each independently, (c1) hydrogen atom; (c2) (C1-C6) alkyl group; (c3) a (C2-C6) alkenyl group; (c4) a (C2-C6) alkynyl group; (c5) (C3-C6) cycloalkyl group; (c6) (C1-C6) alkoxy group; (c7) halo(C1-C6)alkyl group; (c8) (C1-C6) alkylthio group; (c9) a (C1-C6) alkylsulfinyl group; (c10) a (C1-C6) alkylsulfonyl group; (c11) (C3-C6) cycloalkylsulfonyl group; (c12) a phenylsulfonyl group; (c13) (C3-C6)cycloalkyl(C1-C6)alkyl group; (c14) (C1-C6)alkoxy(C1-C6)alkylcarbonyl group; (c15) (C1-C6)alkoxy(C1-C6)alkyl group; (c16) di(C1-C6)alkoxy(C1-C6)alkyl group; (c17) cyano(C1-C6)alkyl groups; (c18) (C1-C6) alkylthio(C1-C6) alkyl group; (c19) di((C1-C6)alkyl)amino(C1-C6)alkyl groups; (c20) (C1-C6) alkylcarbonyl group; (c21) halo(C1-C6)alkylcarbonyl group; (c22) (C3-C6) cycloalkylcarbonyl group; (c23) benzoyl group; (c24) mono((C1-C6)alkyl)aminocarbonyl group; (c25) di((C1-C6)alkyl)aminocarbonyl group; (c26) a phenylaminocarbonyl group; (c27) (C1-C6)alkoxycarbonyl(C1-C6)alkyl group; (c28) a phenylcarbonyl group; (c29) (C1-C6)alkoxyiminomethylene group; (c30) tetrahydropyran-4-ylcarbonyl group; (c31) a benzyl group; (c32) a phenyl group; (c33) a halo-substituted phenyl group; (c34) a formyl group; or (c35) A pyrimidinyl group. R 5 teeth, (d1) hydrogen atom; (d2) (C1-C6) alkyl group; (d3) (C1-C6) alkylcarbonyl group; (d4) a (C1-C6) alkoxycarbonyl group; or (d5) (C1-C6) alkyl (C1-C6) alkyl group.} or a salt thereof, [2] Q: (a1) (C1-C6) alkyl group; (a11) (C1-C6) alkylthio group; (a12) (C1-C6) alkylsulfinyl group; (a13) (C1-C6) alkylsulfonyl group; (a17) R 3 (R 4 ) N group; or (a21) each independently represents a halogen atom, a cyano group, a nitro group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, a halo(C1-C6)alkoxy group, a halo(C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylthio group, a halo(C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfonyl group, R 3 (R 4 )N group, (C1-C6)alkylthio(C1-C6)alkyl group, phenyl group, halogen-substituted phenoxy group, (C1-C6)alkoxycarbonyl group and R 3 (R 4 ) a substituted 5- or 6-membered heterocycle or a substituted 8- or 10-membered fused heterocycle having on the ring 1 to 3 substituents selected from the group consisting of N-carbonyl groups, R 1 and R 2 are each independently, (b1) a hydrogen atom; (b3) a (C1-C6) alkyl group; or (b5) (C1-C6) alkoxy group; R 3 and R 4 are each independently, (c1) hydrogen atom; (c2) (C1-C6) alkyl group; (c3) a (C2-C6) alkenyl group; (c4) a (C2-C6) alkynyl group; (c5) (C3-C6) cycloalkyl group; (c6) (C1-C6) alkoxy group; (c10) a (C1-C6) alkylsulfonyl group; (c11) (C3-C6) cycloalkylsulfonyl group; (c12) a phenylsulfonyl group; (c13) (C3-C6)cycloalkyl(C1-C6)alkyl group; (c14) (C1-C6)alkoxy(C1-C6)alkylcarbonyl group; (c16) di(C1-C6)alkoxy(C1-C6)alkyl group; (c17) cyano(C1-C6)alkyl groups; (c20) (C1-C6) alkylcarbonyl group; (c21) halo(C1-C6)alkylcarbonyl group; (c22) (C3-C6) cycloalkylcarbonyl group; (c23) benzoyl group; (c24) mono((C1-C6)alkyl)aminocarbonyl group; (c26) a phenylaminocarbonyl group; (c27) (C1-C6)alkoxycarbonyl(C1-C6)alkyl group; (c29) (C1-C6)alkoxyiminomethylene group; (c30) tetrahydropyran-4-ylcarbonyl group; (c33) a halo-substituted phenyl group; (c34) a formyl group; or (c35) a pyrimidinyl group, R 5 but, (d1) a hydrogen atom; or (d2) The compound according to the above [1] or a salt thereof, which represents a (C1-C6) alkyl group; [3] Q: (a13) (C1-C6) alkylsulfonyl group; (a17) R 3 (R 4 ) N group; or (a21) each independently represents a halogen atom, a cyano group, a nitro group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, a halo(C1-C6)alkoxy group, a halo(C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylthio group, a halo(C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfonyl group, R 3 (R 4 )N group, (C1-C6)alkylthio(C1-C6)alkyl group, phenyl group, halogen-substituted phenoxy group, (C1-C6)alkoxycarbonyl group and R 3 (R 4 ) a substituted 5- or 6-membered heterocycle or a substituted 8- or 10-membered fused heterocycle having on the ring 1 to 3 substituents selected from the group consisting of N-carbonyl groups, R 3 and R 4 are each independently, (c1) hydrogen atom; (c2) (C1-C6) alkyl group; (c10) a (C1-C6) alkylsulfonyl group; (c14) (C1-C6)alkoxy(C1-C6)alkylcarbonyl group; (c20) (C1-C6) alkylcarbonyl group; (c22) (C3-C6) cycloalkylcarbonyl group; (c23) benzoyl group; (c24) mono((C1-C6)alkyl)aminocarbonyl group; (c30) tetrahydropyran-4-ylcarbonyl group; (c34) a formyl group; or (c35) a pyrimidinyl group, R 5 but, (d1) The compound or salt thereof according to the above [1] or [2], which represents a hydrogen atom. [4] A disinfectant comprising the compound or salt thereof according to any one of [1] to [3] above as an active ingredient. [5] A method for controlling plant diseases, comprising applying an effective amount of the fungicide according to [4] to a plant or soil. [6] Use of the compound or a salt thereof according to any one of the above [1] to [3] as a fungicide. Effect of the Invention

[0007] The compound of the present invention or a salt thereof has an excellent effect as an agricultural and horticultural fungicide. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] In the definition of the general formula (I) of the compound of the present invention, The term "halo" means a "halogen atom" and refers to a chlorine atom, bromine atom, iodine atom, or fluorine atom.

[0009] The term "(C1-C6) alkyl group" refers to a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, such as a methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group, tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group, 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group, or 3,3-dimethylbutyl group.

[0010] The term "(C2-C6) alkenyl group" refers to a linear or branched alkenyl group having 2 to 6 carbon atoms, such as a vinyl group, an allyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 2-methyl-2-propenyl group, a 1-methyl-2-propenyl group, a 2-methyl-1-propenyl group, a pentenyl group, a 1-hexenyl group, or a 3,3-dimethyl-1-butenyl group. The term "6) alkynyl group" refers to a straight-chain or branched-chain alkynyl group having 2 to 6 carbon atoms, such as an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 3-methyl-1-propynyl group, a 2-methyl-3-propynyl group, a pentynyl group, a 1-hexynyl group, a 3-methyl-1-butynyl group, or a 3,3-dimethyl-1-butynyl group.

[0011] The "(C3-C6) cycloalkyl group" refers to a cyclic alkyl group having 3 to 6 carbon atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and the "(C1-C6) alkoxy group" refers to a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms, such as a methoxy group, an ethoxy group, a normal propoxy group, an isopropoxy group, a normal butoxy group, a secondary butoxy group, a tertiary butoxy group, a normal pentyloxy group, an isopentyloxy group, a tertiary pentyloxy group, a neopentyloxy group, a 2,3-dimethylpropyloxy group, a 1-ethylpropyloxy group, a 1-methylbutyloxy group, a normal hexyloxy group, an isohexyloxy group, or a 1,1,2-trimethylpropyloxy group.

[0012] The term "(C1-C6) alkylthio group" refers to a linear or branched alkylthio group having 1 to 6 carbon atoms, such as a methylthio group, ethylthio group, normal propylthio group, isopropylthio group, normal butylthio group, secondary butylthio group, tertiary butylthio group, normal pentylthio group, isopentylthio group, tertiary pentylthio group, neopentylthio group, 2,3-dimethylpropylthio group, 1-ethylpropylthio group, 1-methylbutylthio group, normal hexylthio group, isohexylthio group, or 1,1,2-trimethylpropylthio group.

[0013] The "(C1-C6)alkylsulfinyl group" refers to a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as a methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, normal pentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, isohexylsulfinyl group, or 1,1,2-trimethylpropylsulfinyl group.

[0014] The term "(C1-C6)alkylsulfonyl group" refers to a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms, such as a methylsulfonyl group, ethylsulfonyl group, normal propylsulfonyl group, isopropylsulfonyl group, normal butylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulfonyl group, isohexylsulfonyl group, or 1,1,2-trimethylpropylsulfonyl group.

[0015] The term "(C1-C6)alkylcarbonyl group" refers to an alkylcarbonyl group having 2 to 7 carbon atoms, such as an alkylcarbonyl group having the above-mentioned (C1-C6)alkyl group, such as an acetyl group, a propanoyl group, a butanoyl group, a 2-methylpropanoyl group, a pentanoyl group, a 2-methylbutanoyl group, a 3-methylbutanoyl group, a pivaloyl group, a hexanoyl group, or a cyclopropylcarbonyl group.

[0016] The "(C1-C6)alkoxycarbonyl group" refers to an alkoxycarbonyl group having 2 to 7 carbon atoms, such as an alkoxycarbonyl group having the above-mentioned (C1-C6) alkoxy group, such as a methoxycarbonyl group, ethoxycarbonyl group, normal propoxycarbonyl group, isopropoxycarbonyl group, normal butoxycarbonyl group, isobutoxycarbonyl group, secondary butoxycarbonyl group, tertiary butoxycarbonyl group, or pentyloxycarbonyl group.

[0017] The above "(C1-C6) alkyl group", "(C2-C6) alkenyl group", "(C2-C6) alkynyl group", "(C3-C6) cycloalkyl group", "(C1-C6) alkoxy group", "(C1-C6) alkylthio group", "(C1-C6) alkylsulfinyl group" or "(C1-C6) alkylsulfonyl group" may be substituted with one or more halogen atoms at substitutable positions, and when there are two or more halogen atoms substituted, the halogen atoms may be the same or different. These groups are respectively represented as "halo(C1-C6) alkyl group", "halo(C2-C6) alkenyl group", "halo(C2-C6) alkynyl group", "halo(C3-C6) cycloalkyl group", "halo(C1-C6) alkoxy group", "halo(C1-C6) alkylthio group", "halo(C1-C6) alkylsulfinyl group" or "halo(C1-C6) alkylsulfonyl group".

[0018] Expressions such as "(C1-C6)", "(C2-C6)", "(C3-C6)" indicate the range of carbon atoms of various substituents. Furthermore, the above definitions can be applied to the groups to which the above substituents are linked, for example, "(C1-C6)alkoxy(C1-C6)alkyl group" indicates that a linear or branched alkoxy group having 1 to 6 carbon atoms is linked to a linear or branched alkyl group having 1 to 6 carbon atoms.

[0019] The terms "aryl group" and "aryl" refer to aromatic hydrocarbon groups having 6 to 10 carbon atoms, such as a phenyl group and a naphthyl group.

[0020] The "5- or 6-membered heterocycle" refers to, for example, the structure shown below, in which · indicates the bonding position. [ka]

[0021] The term "8- to 10-membered fused heterocycle" refers to, for example, the structure shown below, in which · indicates the bonding position. [ka]

[0022] Examples of salts of the compound represented by general formula (I) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate; organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, and paratoluenesulfonate; and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium.

[0023] The compound represented by the general formula (I) of the present invention and its salts may have one or more asymmetric centers in the structural formula, and may have two or more optical isomers and diastereomers, and the present invention includes all of the optical isomers and mixtures containing them in any ratio. The compound represented by the general formula (I) of the present invention and its salts may have two geometric isomers derived from a carbon-carbon double bond in the structural formula, and the present invention includes all of the geometric isomers and mixtures containing them in any ratio.

[0024] In the compound represented by the general formula (I) of the present invention, preferred embodiments are shown below. Q is preferably (a1) (C1-C6) alkyl group; (a11) (C1-C6) alkylthio group; (a12) (C1-C6) alkylsulfinyl group; (a13) (C1-C6) alkylsulfonyl group; (a17) R 3 (R 4 ) N group; or (a21) each independently represents a halogen atom, a cyano group, a nitro group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, a halo(C1-C6)alkoxy group, a halo(C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylthio group, a halo(C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfonyl group, R 3 (R 4 )N group, (C1-C6)alkylthio(C1-C6)alkyl group, phenyl group, halogen-substituted phenoxy group, (C1-C6)alkoxycarbonyl group and R 3 (R 4 ) a substituted 5- or 6-membered heterocycle or a substituted 8- or 10-membered fused heterocycle having on the ring 1 to 3 substituents selected from the group consisting of N-carbonyl groups, More preferably, (a13) (C1-C6) alkylsulfonyl group; (a17) R 3 (R 4 ) N group; or (a21) each independently represents a halogen atom, a cyano group, a nitro group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, a halo(C1-C6)alkoxy group, a halo(C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylthio group, a halo(C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfonyl group, R 3 (R 4 )N group, (C1-C6)alkylthio(C1-C6)alkyl group, phenyl group, halogen-substituted phenoxy group, (C1-C6)alkoxycarbonyl group and R 3 (R 4 ) a substituted 5- or 6-membered heterocycle or a substituted 8- to 10-membered fused heterocycle having on the ring 1 to 3 substituents selected from the group consisting of N-carbonyl groups. R 1 and R 2 Preferably, each independently is (b1) a hydrogen atom; (b3) a (C1-C6) alkyl group; or (b5) a (C1-C6)alkoxy group; More preferably, each independently: (b1) a hydrogen atom; or (b3) is a (C1-C6) alkyl group. R 3 and R 4 Preferably, each independently is (c1) hydrogen atom; (c2) (C1-C6) alkyl group; (c3) a (C2-C6) alkenyl group; (c4) a (C2-C6) alkynyl group; (c5) (C3-C6) cycloalkyl group; (c6) (C1-C6) alkoxy group; (c10) a (C1-C6) alkylsulfonyl group; (c11) (C3-C6) cycloalkylsulfonyl group; (c12) a phenylsulfonyl group; (c13) (C3-C6)cycloalkyl(C1-C6)alkyl group; (c14) (C1-C6)alkoxy(C1-C6)alkylcarbonyl group; (c16) di(C1-C6)alkoxy(C1-C6)alkyl group; (c17) cyano(C1-C6)alkyl groups; (c20) (C1-C6) alkylcarbonyl group; (c21) halo(C1-C6)alkylcarbonyl group; (c22) (C3-C6) cycloalkylcarbonyl group; (c23) benzoyl group; (c24) mono((C1-C6)alkyl)aminocarbonyl group; (c26) a phenylaminocarbonyl group; (c27) (C1-C6)alkoxycarbonyl(C1-C6)alkyl group; (c29) (C1-C6)alkoxyiminomethylene group; (c30) a tetrahydropyran-4-ylcarbonyl group; or (c33) a halo-substituted phenyl group; More preferably, each independently: (c1) hydrogen atom; (c2) (C1-C6) alkyl group; (c10) a (C1-C6) alkylsulfonyl group; (c14) (C1-C6) alkoxy(C1-C6) alkylcarbonyl group (c20) (C1-C6) alkylcarbonyl group; (c23) benzoyl group; (c24) a mono((C1-C6) alkyl)aminocarbonyl group; or (c30) A tetrahydropyran-4-ylcarbonyl group. R 5 As the preferable (d1) a hydrogen atom; or (d2) a (C1-C6) alkyl group; More preferably, (d1) It is a hydrogen atom. Among the compounds or salts of the present invention, those with low HDAC4 inhibitory activity are preferred. HDAC exhibits multifaceted actions, and its inhibitors are expected to be used as anticancer drugs. However, due to its multifaceted nature, nonselective inhibition or excessive inhibition may cause various toxicities such as teratogenicity, as described in literature (Herberland, M., Nat. Rev. Genet., 2009, 10, 32-42. and Current Pharmaceutical Design, 2014, Vol. 20, No. 00).

[0025] The various compounds of the present invention can be produced, for example, by the production methods described below, but the production methods of the compounds of the present invention are not limited to these.

[0026] Manufacturing method 1 [ka] (Wherein, L, Q and R 5 has the same meaning as above, and X represents a leaving group such as a halogen atom, a mesyl group, a tosyl group, or a triflate group.

[0027] The compounds of the present invention represented by general formulas (I-1) and (I-2) can be produced by the above-mentioned and following steps [a] and [b], but the compounds of the present invention and the production methods thereof are not limited thereto. Step [a]: A step of producing a compound represented by general formula (I-1) by reducing a compound represented by general formula (3). Step [b]: A step of producing a compound represented by general formula (I-2) by reacting a compound represented by general formula (I-1) with a compound represented by general formula (2).

[0028] Manufacturing method of step [a] The compound represented by the general formula (I-1) can be produced by the method described in WO 2019 / 131867, WO 2017 / 213252, WO 2017 / 055473, WO 2015 / 185485, WO 2017 / 118689, WO 2017 / 080859, WO 2013 / 008162, WO 2017 / 076935, WO 2015 / 185485 and JP-A-63-162680. It can be produced by reacting the compound represented by the general formula (3) with a reducing agent in an inert solvent.

[0029] Examples of the reducing agent that can be used in this reaction include lithium aluminum hydride, sodium aluminum hydride, sodium borohydride, and sodium cyanoborohydride. The amount of the reducing agent used can be appropriately selected usually from the range of 0.25 to 2 times the molar amount of the compound represented by the general formula (3).

[0030] The inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and may be, for example, aliphatic hydrocarbons such as pentane, hexane, cyclohexane, etc.; ethers such as diethyl ether, methyl tertiary butyl ether, cyclopentyl methyl ether, tetrahydrofuran, dioxane, etc.; alcohols such as methanol, ethanol, 1-propanol, 2-propanol, etc. These inert solvents may be used alone or in combination of two or more. The amount of the solvent used may be appropriately selected from the range of usually 0.1 to 100 L per mole of the compound represented by the general formula (3).

[0031] Since this reaction is an equimolar reaction, each reactant may be used in equimolar amounts, but any one of the reactants may be used in excess. The reaction temperature is usually from room temperature to the boiling point range of the inert solvent used, and the reaction time varies depending on the reaction scale and reaction temperature, but is usually within a range of several minutes to 48 hours. After the reaction is completed, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc. as necessary.

[0032] Manufacturing method of step [b] The compound represented by general formula (I-2) can be produced by reacting a compound represented by general formula (I-1) with a compound represented by general formula (2) in the presence of a base in an inert solvent.

[0033] Examples of bases that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as potassium t-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine, and 1,8-diazabicyclo[5.4.0]undec-7-ene; and nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine. The amount of base used can be appropriately selected from the range of usually 1 to 5 times the molar amount of the compound represented by the general formula (I-1).

[0034] The inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, cyclopentyl methyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methyl ethyl ketone; aprotic polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents may be used alone or in combination. The amount of the solvent used may be appropriately selected from the range of 0.1 to 100 L per mole of the compound represented by the general formula (I-1).

[0035] Since this reaction is an equimolar reaction, each reactant may be used in equimolar amounts, but any one of the reactants may be used in excess. The reaction temperature is usually from room temperature to the boiling point range of the inert solvent used, and the reaction time varies depending on the reaction scale and reaction temperature, but is usually within a range of several minutes to 48 hours. After the reaction is completed, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc. as necessary.

[0036] Representative examples of the compounds represented by general formula (I) of the present invention are shown in Tables 1 to 3 below, but the present invention is not limited to these. In the table, "Me" stands for methyl, "Et" stands for ethyl, "n-Pr" stands for normal propyl, "i-Pr" stands for isopropyl, "n-Bu" stands for normal butyl, "i-Bu" stands for isobutyl, "sec-Bu" stands for secondary butyl, "t-Bu" stands for tertiary butyl, "Ph" stands for phenyl, "cyc-Pr" stands for cyclopropyl, and "cyc-Hex" stands for cyclohexyl. Physical properties are melting point (℃) or refractive index n D (Measurement temperature).

[0037]

change

[0038]

Table 1

[0039]

Table 2

[0040]

Table 3

[0041]

Table 4

[0042]

Table 5

[0043]

Table 6

[0044]

change

[0045]

Table 7

[0046]

Table 8

[0047]

change

[0048]

Table 9

[0049]

Table 10

[0050]

Table 11

[0051]

Table 12

[0052]

Table 13

[0053]

Table 14

[0054]

Table 15

[0055]

Table 16

[0056]

Table 17

[0057] [Table 18]

[0058] [Table 19]

[0059] Agricultural and horticultural fungicides containing the compound represented by the general formula (I) of the present invention or a salt thereof as an active ingredient are suitable for controlling diseases occurring in grains, fruit trees, vegetables, other crops and ornamental plants.

[0060] Target diseases include fungal diseases, bacterial diseases, and viral diseases. Examples of fungal diseases include diseases caused by imperfect fungi (e.g., diseases of the genus Botrytis, Helminthosporium, Fusarium, Septoria, Cercospora, Pseudocercosporella, Rhynchosporium, Pyricularia, Alternaria, etc.); diseases caused by basidiomycetes (e.g., diseases of the genus Hemilelia, Rhizoctonia, Ustilago, Typhula, Puccinia, etc.); Diseases caused by ascomycetes (e.g., Venturia, Podosphaera, Leptosphaeria, Blumeria, Erysiphe, Microdochium, Sclerotinia, Gaeumannomyces, Monilinia, Unsinula, etc.); and diseases caused by other fungi (e.g., Ascochyta, Phoma, Pythium, Corticium, Pyrenophora, etc.). Examples of bacterial diseases include diseases caused by the genus Pseudomonas, Xanthomonas, and Erwinia. Examples of viral diseases include diseases caused by the tobacco mosaic virus.

[0061] Specific examples of fungal diseases include rice blast (Pyricularia oryzae), rice sheath blight (Rhizoctonia solani), rice brown spot (Cochiobolus miyabeanus), rice seedling damping-off (Rhizopus chinensis, Pythium graminicola, Fusarium graminicola, Fusarium roseum, Mucor sp., Phoma sp., Tricoderma sp.), rice seedling blight (Gibberella fujikuroi), powdery mildew of barley and wheat (Blumeria graminis), powdery mildew of cucumber (Sphaerotheca fuliginea), powdery mildew of eggplant (Erysiphe cichoracoarum), powdery mildew of other host plants, eyespot disease of barley and wheat (Pseudocercosporella herpotrichoides), smut of wheat (Urocystis tritici), snow mold of barley and wheat (Microdochium nivalis, Pythium iwayamai, Typhla ishikariensis, Typhla incarnata, Sclerotinia borealis), red mold disease of barley and wheat (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivalis), rust of barley and wheat (Puccinia recondita, Puccinia striiformis,Puccinia graminis, Gaeumannomyces graminis, crown rust of oats, and other plant rusts, Botrytis cinerea, gray mold of cucumbers and strawberries, Sclerotinia sclerotiorum, Phytophthora infestans, and other plant diseases, such as cucumber downy mildew, Pseudoperonospora cubensis, grape downy mildew, Venturia inaequalis, Alternaria mali, Alternaria kikuchiana, Diaporthe citri, citrus scab, Elsinoe fawcetti, sugar beet brown spot (Cercospora beticola), peanut brown spot (Cercospora arachidicola), peanut black spot (Cercospora personata), wheat leaf blight (Septoria tritici), wheat leaf spot (Leptosphaeria nodorum), barley net blotch (Pyrenophora teres), barley leaf spot (Pyrenophora graminea), barley scald (Rhynchosporium secalis), wheat naked smut (Ustilago nuda), wheat smut (Tilletia caries), turfgrass leaf blight (Rhizoctonia solani), turfgrass dollar spot (Sclerotinia homoeocarpa), etc.

[0062] Specific examples of bacterial diseases include diseases caused by the genus Pseudomonas, such as cucumber bacterial spot (Pseudomonas syringae pv. lachrymans), tomato bacterial wilt (Pseudomonas solanacearum), and rice bacterial blight (Pseudomonas glumae); diseases caused by the genus Xanthomonas, such as cabbage black rot (Xanthomonas campestris), rice bacterial leaf blight (Xanthomonas oryzae), and citrus canker (Xanthomonas citri); and diseases caused by the genus Erwinia, such as cabbage soft rot (Erwinia carotovora).

[0063] Useful plants for which the compound represented by the general formula (I) of the present invention or a salt thereof can be used are not particularly limited, and examples thereof include cereals (e.g., rice, barley, wheat, rye, oats, corn, etc.), beans (soybeans, adzuki beans, broad beans, peas, kidney beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, etc.), leafy vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, green onion (chives, scallions), green peppers, eggplant, strawberries, peppers, okra, Chinese chives, etc.), root vegetables (carrots, potatoes, sweet potatoes, taro, daikon radishes, turnips, lotus roots, burdock, Examples of plants that can be used include crops for processing (cotton, hemp, beets, hops, sugar cane, sugar beets, olives, rubber, coffee, tobacco, tea, etc.), melons (pumpkin, cucumber, watermelon, Sakwau-ri, melon, etc.), pasture grasses (orchard grass, sorghum, timothy, clover, alfalfa, etc.), turfgrass (Korean grass, bentgrass, etc.), ornamental crops for flavorings (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemum, rose, carnation, orchid, tulip, lily, etc.), garden trees (ginkgo, cherry trees, Japanese cypress, etc.), and forest trees (abarch firs, spruces, pines, Japanese cypress, cedar, cypress, eucalyptus, etc.).

[0064] The above-mentioned "plant" also includes plants to which resistance has been imparted by classical breeding methods or genetic engineering techniques to HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, acetyl-CoA carboxylase inhibitors such as sethoxydim, and herbicides such as bromoxynil, dicamba, and 2,4-D.

[0065] Examples of "plants" that have been given resistance by classical breeding methods include rapeseed, wheat, sunflower, and rice that are resistant to imidazolinone ALS inhibitor herbicides such as imazethapyr, which are already sold under the trade name Clearfield (registered trademark). Similarly, soybeans that have been resistant to sulfonylurea ALS inhibitor herbicides such as thifensulfuron methyl by classical breeding methods are already sold under the trade name STS soybeans. Similarly, examples of plants that have been given resistance to acetyl-CoA carboxylase inhibitors such as trione oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods include SR corn. Furthermore, plants to which resistance to acetyl-CoA carboxylase inhibitors has been imparted are described in Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA), Vol. 87, pp. 7175-7179 (1990), and the like. In addition, mutant acetyl-CoA carboxylases resistant to acetyl-CoA carboxylase inhibitors have been reported in Weed Science, Vol. 53, pp. 728-746 (2005), and the like. By introducing such mutant acetyl-CoA carboxylase genes into plants by recombinant gene technology or by introducing a mutation associated with conferring resistance into plant acetyl-CoA carboxylase, it is possible to produce plants resistant to acetyl-CoA carboxylase inhibitors. Furthermore, by introducing a nucleic acid with a base substitution mutation, as typified by the chimeraplasty technique (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.), into plant cells to introduce a site-specific amino acid substitution mutation into the acetyl-CoA carboxylase gene, ALS gene, or the like of a plant, it is possible to produce plants resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, or the like. The compound represented by the general formula (I) of the present invention or a salt thereof can also be used for these plants.

[0066] Further toxins expressed in transgenic plants include insecticidal proteins from Bacillus cereus and Bacillus popilia; delta-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C from Bacillus thuringiensis; insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, wasp toxins or insect-specific neurotoxins; fungal toxins; plant lectins; agglutinins; trypsin inhibitors, serine protease inhibitors, patatin, cysta These include protease inhibitors such as ricin and papain inhibitors; ribosome-inactivating proteins (RIPs) such as ricin, maize-RIP, abrin, rufin, saporin, and bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, and cholesterol oxidase; ecdysone inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium channel and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase, etc.

[0067] Toxins expressed in such transgenic plants also include δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, or Cry35Ab; hybrid toxins of insecticidal proteins such as VIP1, VIP2, VIP3, or VIP3A; toxins with partial deletions; and modified toxins. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant technology. One known example of a toxin with partial deletions is Cry1Ab, which has a partial deletion in its amino acid sequence. Modified toxins have one or more amino acids substituted in the natural toxin.

[0068] Examples of these toxins and recombinant plants capable of synthesizing these toxins are described in EP-A-0 374 753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878, WO 03 / 052073, etc.

[0069] The agricultural and horticultural fungicide of the present invention can be used in combination with these techniques or as a system thereof.

[0070] The agricultural and horticultural fungicide of the present invention may be applied to plants where the occurrence of various diseases is predicted, either as it is or after being appropriately diluted or suspended in water, in an amount effective for disease control, and for diseases occurring in fruit trees, grains, vegetables, etc., it may be sprayed on the stems and leaves, or may be used by immersing seeds in the fungicide, seed dressing, seed treatment such as Calper treatment, mixing into the entire soil layer, row application, mixing into bed soil, cell seedling treatment, planting hole treatment, plant base treatment, top dressing, rice box treatment, water surface application, etc., or by application to soil, etc. and absorption through the roots. In addition, it may be applied to nutrient solution in nutrient solution (hydroponic) cultivation, smoked, or injected into tree trunks, etc.

[0071] Furthermore, the agricultural and horticultural fungicide of the present invention may be used in an amount effective for disease control as it is, or after being appropriately diluted or suspended in water or the like, in a location where the occurrence of the disease is predicted.

[0072] Seed treatment methods include, for example, a method in which seeds are soaked in a liquid or solid formulation, either diluted or undiluted, to allow the agent to penetrate the seeds; a method in which a solid or liquid formulation is mixed with seeds and dusted to adhere to the seed surface; a method in which the formulation is mixed with an adhesive carrier such as a resin or polymer and then coated on the seeds; and a method in which the formulation is sprayed around the seeds at the same time as planting. The "seed" to be subjected to the seed treatment means a plant body in the early stage of cultivation used for plant propagation, and examples thereof include seeds, as well as bulbs, tubers, seed potatoes, sprouts, corms, bulbs, or plant bodies for vegetative propagation for cultivation by cuttings.

[0073] The "soil" or "cultivation carrier" for a plant when carrying out the method of use of the present invention refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited as long as it is a material in which plants can grow, and may be so-called soil, seedling mat, water, etc., and specific materials may be, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, polymeric substances, rock wool, glass wool, wood chips, bark, etc.

[0074] Methods for spraying on crop stems and leaves include a method in which a liquid formulation such as an emulsifiable concentrate or flowable concentrate, or a solid formulation such as a wettable powder or water dispersible granules is appropriately diluted with water and sprayed, a method in which a powder is sprayed, or fumigation.

[0075] Methods for application to soil include, for example, applying a liquid formulation, with or without dilution, to the base of a plant or a seedbed for raising seedlings, etc.; spraying a granule at the base of a plant or a seedbed for raising seedlings, etc.; spraying a dust, wettable powder, water dispersible granule, granule, etc. and mixing it with the entire soil before sowing or transplanting; and spraying a dust, wettable powder, water dispersible granule, granule, etc. in planting holes, rows, etc. before sowing or planting plants.

[0076] For application to rice seedling boxes, the formulation may be in the form of a dust, water dispersible granule, granule, etc., depending on the application time, for example, application at the time of sowing, application during the greening period, application at the time of transplanting, etc. Application can also be by mixing with the culture soil, and the culture soil can be mixed with a dust, water dispersible granule, or granule, for example, by mixing with the bed soil, covering soil, or the entire culture soil. It may also be applied by simply layering the culture soil and various formulations alternately.

[0077] For application to paddy fields, solid preparations such as jumbo, pack, granule, and granular water dispersible agent, or liquid preparations such as flowable and emulsion are usually sprayed on flooded paddy fields. In addition, at the time of rice planting, appropriate preparations can be sprayed or injected into the soil as they are or mixed with fertilizer. In addition, by using emulsion, flowable, or other liquids at the water inlet of paddy fields such as water inlets and irrigation equipment, application can be labor-saving along with the water supply.

[0078] In field crops, the treatment can be applied to the seeds or to the cultivation carriers adjacent to the plant body during the sowing to seedling raising period. In the case of plants that are directly sown in the field, in addition to direct treatment to the seeds, treatment to the base of the plant during cultivation is preferred. Spraying treatment can be performed using granules, or irrigation treatment can be performed in liquid form with or without dilution in water. Another preferred treatment is to mix the granules with the cultivation carrier before sowing and then sowing.

[0079] As treatments for cultivated plants to be transplanted during the sowing and seedling raising stage, in addition to direct treatment of seeds, irrigation of liquid agents or spraying of granules on seedling beds is preferred. It is also preferred to apply granules to the planting hole at the time of planting or to mix them into the cultivation carrier near the transplanting site.

[0080] The compound represented by the general formula (I) of the present invention or a salt thereof is generally formulated into a convenient form for use according to the conventional method for formulating agricultural chemicals.

[0081] That is, the compound represented by the general formula (I) of the present invention or a salt thereof may be mixed in an appropriate ratio with an appropriate inert carrier, or if necessary, with an auxiliary, and then dissolved, separated, suspended, mixed, impregnated, adsorbed or attached to the carrier to prepare an appropriate formulation, such as a suspension (flowable agent), emulsion, oil, liquid, wettable powder, wettable granule, granules, powder, tablet, pack, jumbo agent, suspoemulsion, etc., for use.

[0082] The agricultural and horticultural fungicide of the present invention may contain, in addition to the active ingredient, additives that are commonly used in agricultural chemical formulations as needed. Examples of additives include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreading agents, spreading agents, antifreezing agents, anticaking agents, disintegrants, and antidecomposition agents. If necessary, preservatives, plant pieces, and the like may also be used as additives. These additives may be used alone or in combination of two or more.

[0083] Examples of solid carriers include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride, organic solid carriers such as synthetic silicic acid, synthetic silicates, starch, cellulose, and plant powders (e.g., sawdust, coconut shells, corn cobs, and tobacco stalks), plastic carriers such as polyethylene, polypropylene, and polyvinylidene chloride, urea, inorganic hollow bodies, plastic hollow bodies, fumed silica (white carbon), etc. These may be used alone or in combination of two or more.

[0084] Examples of liquid carriers include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin; polyhydric alcohol compounds such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; ethers such as ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, and THF; normal paraffin; naphthene; Examples of the solvent include aliphatic hydrocarbons such as isoparaffin, kerosene, and mineral oil, aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, and alkylnaphthalene, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate, lactones such as γ-butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, and N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethyl sulfoxide, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil, and water. These may be used alone or in combination of two or more.

[0085] Examples of surfactants used as dispersants or wetting agents include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene dialkylphenyl ethers, polyoxyethylene alkylphenyl ether formalin condensates, polyoxyethylene polyoxypropylene block copolymers, polystyrene polyoxyethylene block polymers, alkyl polyoxyethylene polypropylene block copolymer ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene fatty acid bisphenyl ethers, polyalkylene benzyl phenyl ethers, polyoxyalkylene styryl phenyl ethers, acetylenic diols, polyoxyalkylene-added acetylenic diols, polyoxyethylene ether-type silicones, ester-type silicones, fluorine nonionic surfactants such as polyoxyethylene castor oil and polyoxyethylene hydrogenated castor oil; anionic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, alkyl benzene sulfonates, alkyl aryl sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkyl naphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkyl naphthalene sulfonic acid, fatty acid salts, polycarboxylates, polyacrylates, N-methyl-fatty acid sarcosinates, resin salts, polyoxyethylene alkyl ether phosphates, and polyoxyethylene alkyl phenyl ether phosphates; cationic surfactants such as alkyl amine salts such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyl trimethylammonium chloride, and alkyl dimethyl benzalkonium chloride;Amphoteric surfactants such as amino acid type or betaine type surfactants can be used alone or in combination of two or more types.

[0086] Examples of binders and tackifiers include carboxymethylcellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol having an average molecular weight of 6,000 to 20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipids (e.g., cephalin, lecithin, etc.), cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compounds, crosslinked polyvinylpyrrolidone, copolymers of maleic acid and styrenes, (meth)acrylic acid copolymers, half esters of polymers composed of polyhydric alcohols and dicarboxylic acid anhydrides, water-soluble salts of polystyrene sulfonic acid, paraffin, terpene, polyamide resins, polyacrylates, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formaldehyde condensates, and synthetic resin emulsions.

[0087] Examples of thickeners include water-soluble polymers such as xanthan gum, guar gum, diutan gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds, and polysaccharides, and inorganic fine powders such as high-purity bentonite and fumed silica (white carbon).

[0088] Examples of colorants include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue, and organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.

[0089] Examples of the antifreeze agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

[0090] Examples of adjuvants for preventing caking or promoting disintegration include polysaccharides such as starch, alginic acid, mannose, and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, sodium hexametaphosphate, metal stearates, cellulose powder, dextrin, methacrylic acid ester copolymers, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compounds, sulfonated styrene-isobutylene-maleic anhydride copolymers, and starch-polyacrylonitrile graft copolymers.

[0091] Examples of the decomposition inhibitor include drying agents such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol compounds, amine compounds, sulfur compounds, and phosphoric acid compounds; and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds.

[0092] Examples of preservatives include potassium sorbate and 1,2-benzothiazolin-3-one.

[0093] Furthermore, other auxiliary agents such as functional spreading agents, activity enhancers such as metabolic decomposition inhibitors such as piperonyl butoxide, antifreeze agents such as propylene glycol, antioxidants such as BHT, and ultraviolet absorbers may also be used as necessary.

[0094] The blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the range of 0.01 to 90 parts by weight per 100 parts by weight of the agricultural and horticultural fungicide of the present invention. For example, when used as a dust, granule, emulsion or wettable powder, 0.01 to 50 parts by weight (0.01 to 50% by weight relative to the total weight of the agricultural and horticultural fungicide) is appropriate.

[0095] The amount of the compound represented by general formula (I) of the present invention or a salt thereof to be used varies depending on various factors, such as the purpose, target weeds, crop growth conditions, weed infestation tendency, weather, environmental conditions, formulation type, application method, application location, application time, etc., but may be appropriately selected depending on the purpose from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, of the active ingredient compound per 10 ares.

[0096] When the agricultural and horticultural fungicide containing the compound represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is used, it is diluted to an appropriate concentration and then sprayed, or it is applied as it is.

[0097] The agricultural and horticultural fungicide of the present invention can be used in combination with other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, biological pesticides, etc., in order to extend the range of diseases to be controlled and the optimal control period, or for the purpose of reducing the amount of drug, and can also be used in combination with herbicides, plant growth regulators, fertilizers, etc., depending on the application scene. Representative compounds are shown below as examples, but are not limited to these.

[0098] Other agricultural and horticultural fungicides used for such purposes include, for example, aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, and the like. alcohol), aldimorph, amobam, isotianil, isovaledione, isopyrazam, isofetamide, isoprothiolane, ipconazole, iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole mibenconazole, uniconazole, uniconazole-P, echlomezole, edifenphos, etaconazole, ethaboxam, ethirimol, etem, ethoxyquin, etridiazole, enestroburin, enoxastrobin, epoxiconazole, oxadixyl, oxathiapiprolin, oxycarboxin,copper-8-quinolinolate, oxytetracycline, copper-oxinate, oxpoconazole, oxpoconazole-fumarate, oxolinic acid acid, octhilinone, ofurace, orysastrobin, metam-sodium and other soil fungicides, kasugamycin, carbamorph, carpropamid, carbendazim, carboxin, carvone, quinazamid, quinacetol, quinoxyfen, chinomethionat, quinomethionate, captafol, captan, kiralaxyl, quinconazole, quintozene, guazatine tine), cufraneb, cuprobam, coumoxystrobin, glyodin, griseofulvin, climbazole, cresol, kresoxim-methyl, chlozolinate, clotrimazole, chlobenthiazone, chloraniformethan, chloranil, chlorquinox, chloropicrin, chlorphenazole, chlorodinitronaphthalene, chlorothalonil,Chloroneb, salicylanilide, zarilamid, cyazofamid, diethyl pyrocarbonate, diethofencarb, cyclafuramid, diclocymet, dichlozoline, diclobutrazol, dichlofluanid, cycloheximide, diclomezine, dicloran, dichlorophen hlorophen, dichlone, disulfiram, ditalimfos, dithianon, diniconazole, diniconazole-M, zineb, dinocap, dinocton, dinosulfon, dinoterbone, dinobut on), dinopenton, dipymetitrone, dipyrithione, diphenylamine, difenoconazole, cyflufenamid, diflumetorim, cyproconazole, cyprodinil, cyprofuram , cypendazole, simeconazole, dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, ziram, silthiofam, streptomycin, spiroxamine, sultropen,Sedaxane, zoxamide, dazomet, thiadiazin, tiadinil, thiadifluor, thiabendazole, tioximid, thiochlorfenphim, thiophanate, thiophanate-methyl, thifluzamide, thicyofen, thioquinox, thiram, decaphentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid acid), tebuconazole, tebufloquin, dodicin, dodine, dodecylbenzenesulfonic acid bisethylenediamine copper complex salt (II) (DBEDC), dodemorph, drazoxolon, triadimenol, triadimefon, triazbutil, triazoxide, triamiphos, triarimol, trichlamide, triclopyricarb, tricyclazole, triticonazole, tridemorph, tributyltin oxide oxide), triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolprocarb,Natamycin, nabam, nitrostyrene, nitrothal-isopropyl, nuarimol, copper nonylphenol sulfonate, halacrinate, validamycin, valifenalate, harpin protein protein), picarbutrazox, bixafen, picoxystrobin, picobenzamide, bithionol, bitertanol, hydroxyisoxazole, hydroxyisoxazole potassium, binapacryl, biphenyl, piperalin, hymexazol, pyraoxystrobin, pyracarbolid, pyraclostrobin, pyraziflumid, pyrazo Pyrazophos, pyrametostrobin, pyriophenone, pyridinitril, pyridiflumetofen, pyridiflumetofen, pyrisoxazole, pyrifenox, pyribencarb, pyrimethanil, pyroxychlor, pyroxyfur, pyroquilon, vinclozolin, famoxadone, fenapanil, fenamidone, fenaminosulf,phenaminestrobin, fenarimol, fenitropan, fenoxanil, ferimzone, ferbam, fentin, fenpiclonil, fenpyrazamine, fenbuconazole, fenfuram, fenpropidin, fenpropimol Fenpropimorph, fenhexamid, phthalide, buthiobate, butylamine, bupirimate, fuberidazole, blasticidin-S, furametpyr, furalaxyl, fluacrypyrim, fluazinam, fluoxastrobin oxastrobin, fluotrimazole, fluopicolide, fluopyram, fluoroimide, furcarbanil, fluxapyroxad, fluquinconazole, fluconazole, furconazole-cis, fludioxonil, flusilazole ( flusilazole), flusulfamide, flutianil, flutolanil, flutriafol, furfural, furmecyclox, flumetover, flumorph, proquinazid, prochloraz, procymidone, prothiocarb,Prothioconazole, propamocarb, propiconazole, propineb, furophanate, probenazole, bromuconazole, hexachlorobutadiene, hexaconazole, hexylthiophos lthiofos, bethoxazin, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, benquinox, penconazole, benzamorf, pencycuron, benzohydroxamic acid acid, benzovindiflupyr, bentaluron, benthiazole, benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, phosdiphen, fosetyl, fosetyl-aluminum, polyoxins, polyoxorim, polycarbamate, folpet, formaldehyde, machine oil oil), maneb, mancozeb, mandipropamid, mandestrobin, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid, methasulfocarb,Metazoxolone, metam, Metam sodium salt (metam-sodium), metalaxyl, metalaxyl-M, metiram, methyl isothiocyanate, methyl dinocap, metconazole, metsulfovax, metfuroxam, metominostrobin, metrafenone, mepanipyrim, mefenoxam, meptyldinocap, mepronil, mebenil, methyl iodide, rabenzazole, methyl bromide, benzalkonium chloride Examples of suitable bactericides include inorganic bactericides such as copper chloride, basic copper chloride, basic copper sulfate, and metallic silver; sodium hypochlorite, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate, sodium hydrogen carbonate, inorganic sulfur, copper compounds such as copper sulfate anhydride, nickel dimethyldithiocarbamate, and 8-hydroxyquinoline copper; zinc sulfate, and copper sulfate pentahydrate.

[0099] Examples of agricultural and horticultural insecticides, acaricides, and nematicides used for similar purposes include: 3,5-xylyl methylcarbamate (XMC), Bacillus thuringiensis aizawai, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis kurstaki, Bacillus thuringiensis tenebrionis, crystal protein toxin produced by Bacillus thuringiensis, BPMC, Bt toxin insecticidal compounds, CPCBS (chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1, 3-Dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O,O-diethyl phosphorothioate (DSP), O-ethyl O-4-nitrophenyl Phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, abamectin, afidopyropen, avermectin-B, amidoflumet, ami Amitraz, alanycarb, aldicarb, aldoxycarb, aldrin, alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, isazofos, isamidofos, isoamidofos, isoxathion, isofenphos,Isoprocarb (MIPC), epsilon-metofluthrin, epsilon-momfluorothrin, ivermectin, imicyafos, imidacloprid, imiprothrin, indoxacarb, esfenvalerate, ethiofencarb, ethion, ethiprole, etho Etoxazole, etofenprox, ethoprophos, etrimfos, emamectin, emamectin-benzoate, endosulfan, empenthrin, oxamyl, oxydemeton-methyl, oxydeprofos (ESP), oxibendazole, oxfendazole, potassium oleate, sodium oleate oleate), cadusafos, kappa-bifenthrin, cartap, carbaryl, carbosulfan, carbofuran, gamma-cyhalothrin, xylylcarb, quinalphos, kinoprene, chinomethionate, cloethocarb, clothianidin, clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyfos, chlordimeform,Chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr, chlorfenson, chlorfenvinphos, chlorfluazuron, chlorobenzilate, chlorobenzoate, chloroprallethrin, dicofol, salithion, cyhalodiamide, cyanophos CYAP), diafenthiuron, diamidafos, cyantraniliprole, theta-cypermethrin, dienochlor, cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin, cyclaniliprole, diclofenthion (ECP), cycloprothrin, dichlorvos (dichlorvos: DDVP), disulfoton, dinotefuryl, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron, cyflumetofen, diflovidadin, cyhexatin, cypermethrin, dimethylvinphos, dimethoate, dimefluthrin, silafluofen, cyromazine, spinetoram, spinosad,spirodiclofen, spirotetramat, spiromesifen, sulfluramid, sulprofos, sulfoxaflor, zeta-cypermethrin, diazinon, tau-fluvalinate, dazomet t), thiacloprid, thiamethoxam, tioxazafen, thiodicarb, thiocyclam, thiosultap, thiosultap-sodium, thionazin, thiometon, deet, dieldrin, tetrachlorvinphos trach1orvinphos, tetradifon, tetraniliprole, tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin, teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, tralopyril, tralomethrin, transfluthrin, triazamate, triazuron, trichlamide, trichlorphon: DEP), triflumezopyrim, triflumuron, tolfenpyrad, naled (BRP), nithiazine,Nitenpyram, novaluron, noviflumuron, hydroprene, vaniliprole, vamidothion, parathion, parathion-methyl, halfenprox, halofenozide, bistrifluron, bisultap, hydramethylnon, hydroxypropyl starch starch, binapacryl, pyflubumide, bifenazate, bifenthrin, pymetrozine, pyraclorfos, pyrafluprole, pyridaphenthion, pyridaben, pyridalyl, pyrifluquinazon, pyriprole (pyriprole), pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methyl, pyrethrins, fipronil, fenazaquin, fenamiphos, phenisobromorate, fenitrothion: MEP), fenoxycarb, fenothiocarb, phenothrin, fenobucarb, fensulfothion, fenthion (MPP), phenthoate (PAP), fenvalerate, fenpyroximate,fenpropathrin, fenbendazole, fosthiazate, formetanate, butathiofos, buprofezin, furathiocarb, prallethrin, fluacrypyrim, fluazaindolizine, fluazinam, fluazuron, fluensulfone, fluxametamide, flucycloxuron, flucythrinate, fluvalinate, flufiprole , flupyradifurone, flupyrazofos, flufenerim, flufenoxystrobin, flufenoxuron, flufenzine, flufenprox, fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flumethrin, flurimfen, prothiofos, protrifenbute, flonicamid, propaphos, propargite (BPPS), profenofos, profluthrin, propoxur (propoxur: PHC), flometoquin, bromopropylate, beta-cyfluthrin, hexaflumuron, hexythiazox, heptafluthrin, heptenophos, permethrin, benclothiaz,bendiocarb, bensultap, benzoximate, benfuracarb, phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet (PMP), polynactins, formetanate, formothion, phorate, machine oil oil), malathion, milbemycin, milbemycin A, milbemectin, mecarbam, mesulfenfos, methomyl, metaldehyde, metaflumizone, methamidophos, metam-ammonium, metam-sodium, methiocarb, methidathion: DMTP), methylisothiocyanate, methylneodecanamide, methylparathion, metoxadiazone, methoxychlor, methoxyfenozide, metofluthrin, methoprene, metolcarb, meperfluthrin, mevinphos, monocrotophos, monosultap, momfluorothrin, lambda-cyhalothrin, ryanodine, lufenuron,Examples of such antibacterial agents include rescalure, resmethrin, lepimectin, rotenone, levamisol hydrochloride, fenbutatin oxide, morantel tartarate, methyl bromide, tricyclohexyltin hydroxide, calcium cyanamide, calcium polysulfide, sulfur, and nicotine sulfate.

[0100] Examples of herbicides used for similar purposes include 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, aclonifen, azafenidin, and acifluorfen. (acifluorfen), aziprothrin, azimsulfuron, asulam, acetochlor, atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid acid), amicarbazone, amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amivudine, amiprophos-methyl, ametridione, ametryn, alachlor, allidochlor, alloxydim, arorac, iofensulfuron ensulfuron, isouron, isocarbamide, isoxachlortole, isoxapyrifop, isoxaflutole, isoxaben, isocil, isonoruron, isoproturon, isopropalin, isopolinate, isomethiozin, inabenfide, ipazine,Ipfencarbazone, iprimidam, imazaquin, imazapic, imazapyr, imazamethapyr, imazamethabenz, imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolebutyric acid acid), uniconazole-P, eglinazine, esprocarb, ethametsulfuron, ethametsulfuron-methyl, ethalfluralin, ethiolate, ethychlozate-ethyl ethyl), etidimuron, ethinofen, ethephon, ethoxysulfuron, ethoxyfen, etnipromid, ethofumesate, etobenzanid, epronaz, erbon, endothal, oxadiazon, oxadiargyl ), oxaziclomefone, oxasulfuron, oxapyrazon, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb, cafenstrole, cambendichlor, carbasulam, carfentrazone,carfentrazone-ethyl, karbutilate, carbetamide, carboxazole, quizalofop, quizalofop-P, quizalofop-ethyl, xylachlor, quinoclamine, quinonamid, quinclorac, quinmerac, cumyluron, cliodinate, glyphosate, glufosinate, glufosinate-P, credazine, clethodim, cloxyfonac, clodinafop, clodinafop-propargyl, clotoluron on), clopyralid, cloproxydim, cloprop, chlorbromuron, clofop, clomazone, chlomethoxynil, chlomethoxyfen, clomeprop, chlorazifop, chlorazine, chlorasulam, cloransulam, cloranoc chloranocryl, chloramben, chloransulam-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron, chlorthal, chlorthiamid, chlortoluron, chlornitrofen,Chlorfenac, chlorfenprop, chlorbufam, chlorflurazole, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chloreturon, chloroxynil, chloroxuron, chloropo chloropon, saflufenacil, cyanazine, cyanatryn, di-allate, diuron, diethamquat, dicamba, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron, cyclopyrimorate opyrimorate, dichlorprop, dichlorprop-P, dichlobenil, diclofop, diclofop-methyl, dichromate, dichloralurea, diquat, cisanilide, disul, siduron, dithiopyr, dinitramine nitramine), cinidon-ethyl, dinosam, cinosulfuron, dinoseb, dinoterb, dinofenate, dinoprop, cyhalofop-butyl, diphenamid, difenoxuron, difenopenten, difenzoquat,Cybutryne, cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn, cypromid, cyperquat, gibberellin, simazine, dimexano, dimethachlor, dimidazon, dimethametham dimethametryn, dimethenamid, simetryn, simeton, dimepiperate, dimefuron, cinmethylin, swep, sulglycapin, sulcotrione, sulfalate, sulfentrazone, sulfosulfuron ), sulfometuron, sulfometuron-methyl, secbumeton, sethoxydim, sebuthylazine, terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyr, thiafenacil, thiencarbazone ncarbazone, thiencarbazone-methyl, thiocarbazil, thioclorim, thiobencarb, thidiazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmetryn,Tetrafluron, thenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione, tembotrione, delaclor, terbacil, terbucarb, terbuchlor, terbuthylazine uthylazine, terbutryn, topramezone, tralkoxydim, triaziflam, triasulfuron, triafamone, tri-allate, trietazine, tricamba, triclopyr, tridiphane, tritac, tritosulfuron tritosulfuron, trifludimoxazin, triflusulfuron, triflusulfuron-methyl, trifluralin, trifloxysulfuron, tripropindan, tribenuron-methyl, tribenuron, trifop, trihopsimene trifopsime, trimeturon, tolpyralate, naptalam, naproanilide, naproamide, nicosulfuron, nitralin, nitrofen, nitrofluorfen, nipyraclofen, neburon, norflurazon,noruron, barban, paclobutrazol, paraquat, parafluron, haloxydine, haloxifen, haloxyfop, haloxyfop-P, haloxyfop-methyl, halosafen, halosulfuron, halosulfuron-methyl losulfuron-methyl, picloram, picolinafen, bicyclopyrone, bispyribac, bispyribac-sodium, pydanon, pinoxaden, bifenox, piperophos, hymexazol, pyraclonil, pyrasulfotole ulfotole, pyrazoxyfen, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazolate, bilanafos, pyraflufen-ethyl, pyriclor, pyridafol, pyrithiobac, pyrithiobac-sodium, pyridate (pyridate), pyriftalid, pyributicarb, pyribenzoxim, pyrimisulfan, pyrimisulfuron, pyriminobac-methyl, pyroxasulfone, pyroxsulam, fenasulam, phenisopham, fenuron,Fenoxasulfone, Fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, phenothiol, fenoprop, phenobenzuron, fenquinotrione, fenthiaprop, fenteracol, fentrazamide, phenmedipham nmedipham, phenmedipham-ethyl, butachlor, butafenacil, butamifos, buthiuron, buthidazole, butyrate, buturon, butenachlor, butroxydim, butralin, flazasulfuron, Flamprop, furyloxyfen, prinachlor, primisulfuron-methyl, fluazifop, fluazifop-P, fluazifop-butyl, fluazolate, fluroxypyr, fluothiuron, fluometuron, fluazifop-methyl, fluazifop-butyl ... fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen, fluoromidine, flucarbazone, flucarbazone-sodium, fluchloralin, flucetosulfuron, fluthiacet,Fluthiacet-methyl, flupyrsulfuron, flufenacet, flufenican, flufenpyr, flupropacil, flupropanate, flupoxam, flumioxazin, flumiclorac, flumiclorac-pentyl yl), flumipropyn, flumezin, fluometuron, flumetsulam, fluridone, flurtamone, fluroxypyr, pretilachlor, proxan, proglinazine, procyazine, prodiamine, prosulfarin lfalin), prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, propanil, propyzamide, propisochlor, prohydrojasmon, propyrisulfuron, propham, profluazole profluazol, profluralin, prohexadione-calcium, propoxycarbazone, propoxycarbazone-sodium, profoxydim, bromacil, brompyrazone, prometryn, prometon, bromoxynil,bromofenoxim, bromobutide, bromobonil, florasulam, florpyrauxifen, hexachloroacetone, hexazinone, pethoxamid, benazolin, penoxsulam, pebulate, beflubutamid, vernolate, perfluidone, bencarbazone, benzadox, benzipram, benzylaminopurine, benzthiazuron, benzphen benzfendizone, bensulide, bensulfuron-methyl, benzoylprop, benzobicyclon, benzofenap, benzofluor, bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine, fomesafen, foramsulfuron, forchlorfenuron, maleic hydrazide hydrazide), mecoprop, mecoprop-P, medinoterb, mesosulfuron, mesosulfuron-methyl, mesotrione, mesoprazine, mesoprotryne,Metazachlor, methazole, metazosulfuron, methabenzthiazuron, metamitron, metamifop, metam, methalpropalin, methiuron, methiozolin, methiobencarb, methyldymron, metoxuron, metosulam, metsul furon, metsulfuron methyl, metflurazon, metobromuron, metobenzuron, methometon, metolachlor, metribuzin, mepiquat chloride, mefenacet, mefluidide, monalide, monisouron, monunuron, monochloroacetic acid Examples of such antibacterial agents include iodosulfuron, iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen, linuron, rimsulfuron, lenacil, rhodethanil, calcium peroxide, and methyl bromide.

[0101] Examples of biological pesticides include virus preparations such as nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), and entomopoxi virus (EPV); microbial pesticides used as insecticides or nematocides such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, and Pasteuria penetrans; and pesticides such as Trichoderma lignorum and Agrobacterium radiobacter. Similar effects can be expected by mixing it with microbial pesticides used as fungicides such as Erwinia carotovora (Neutrophil gram-negative bacteria), non-pathogenic Erwinia carotovora (Bacillus subtilis), and biological pesticides used as herbicides such as Xanthomonas campestris.

[0102] Further, examples of biological pesticides include natural enemies such as Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusa sibirica, Phytoseiulus persimilis, Amblyseius cucumeris, and Orius sauteri; It is also possible to use it in combination with microbial pesticides such as Azotobacter brongniartii, and pheromone agents such as (Z)-10-tetradecenyl acetate, (E,Z)-4,10-tetradecadinyl acetate, (Z)-8-dodecenyl acetate, (Z)-11-tetradecenyl acetate, (Z)-13-icosen-10-one, and 14-methyl-1-octadecene.

[0103] Representative examples of the present invention are given below, but the present invention is not limited to these. EXAMPLES

[0104] Example 1 Preparation of N-cyclopropyl-5-[5-(trifluoromethyl)-4,5-dihydro-1,2,4-oxadiazol-3-yl]thiophene-2-carboxamide (compound no. 2-5) [ka] N-cyclopropyl-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiophene-2-carboxamide (0.30 g, 0.90 mmol) was dissolved in methanol (5 mL), cooled to 0°C, sodium borohydride (0.0075 g, 0.20 mmol) was added, and the mixture was stirred at room temperature for 1.3 hours. Then, acetone (1 mL) was added, the mixture was stirred at room temperature for 1 hour, silica gel was added, and the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (0.23 g, 0.67 mmol). Yield: 75% Physical properties: Melting point 237-240℃

[0105] Reference example 1 Preparation of N-cyclopropyl-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiophene-2-carboxamide [ka] 5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiophene-2-carboxylic acid (0.20 g, 0.76 mmol) produced by the method described in International Publication No. 2011 / 088181 was dissolved in chloroform (7 mL), cyclopropylamine (0.056 g, 0.99 mmol), triethylamine (0.23 g, 2.3 mmol), and propylphosphonic anhydride (cyclic trimer) (50% ethyl acetate solution, approximately 1.7 mol / L) (0.97 g, 1.5 mmol) were added, and the mixture was stirred at room temperature for 3.5 hours. Water was then added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over sodium sulfate, and concentrated under reduced pressure. The residue was washed with a mixed solvent of hexane and ethyl acetate to obtain the title compound (0.20 g, 0.67 mmol). Yield: 88% Physical properties: Melting point 179-180℃

[0106] Examples of formulations are shown below, but the present invention is not limited to these. In the formulation examples, parts indicate parts by weight.

[0107] Formulation example 1. 10 parts of the compound represented by the general formula (I) of the present invention Xylene 70 parts N-Methylpyrrolidone 10 parts Polyoxyethylene nonylphenyl ether Mixture with calcium alkylbenzene sulfonate 10 parts The above ingredients are mixed and dissolved uniformly to prepare an emulsion.

[0108] Formulation example 2. Compounds represented by general formula (I) of the present invention Part 3 82 parts clay powder 15 parts diatomaceous earth powder The above ingredients are mixed and ground uniformly to obtain a powder.

[0109] Formulation example 3. Compound represented by general formula (I) of the present invention Part 5 90 parts of bentonite and clay powder mixture Calcium lignosulfonate 5 parts The above ingredients are mixed uniformly, an appropriate amount of water is added, the mixture is kneaded, granulated, and dried to give granules.

[0110] Formulation example 4. 20 parts of the compound represented by the general formula (I) of the present invention A mixture of kaolin and synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether Mixture with calcium alkylbenzene sulfonate 5 parts The above ingredients are mixed uniformly and pulverized to prepare a wettable powder.

[0111] Test Example 1. Fungicidal effect test against soybean rust A drug containing the compound represented by the general formula (I) of the present invention as an active ingredient, prepared according to Formulation Examples 1 to 4, was diluted with water to a predetermined concentration and sprayed on the foliage of soybeans (variety: Enrei, 2-leaf stage) grown in pots with a diameter of 6 cm at a rate of 10 ml per pot. After the drug solution was air-dried, a spore suspension prepared from spores obtained from soybean leaves infected with soybean rust fungus (Phakopsora pachyrhizi) was sprayed and inoculated, and the mixture was kept at 20°C under humidified conditions for 24 hours, and then moved to a greenhouse and left there for about 10 days. The evaluation was carried out by assessing the diseased area ratio for each type, and the control value was calculated using the following formula 1. (Formula 1)

[0112]

number

[0113] As a result of the above test, among the compounds represented by general formula (I) of the present invention, 1-1, 1-11, 1-14, 1-16, 1-20, 1-23, 1-25, 1-31, 1-32, 1-33, 1-35, 1-36, 1-37, 1-38, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45, 1-46, 1-49, 2-1, 2-5, 2-8, 2-23, 3-1, 3-17, 3-43, 3-44, 3-54, 3-60, 3-64, 3-67, 3-68, 3-69, 3-89 and 3-97 showed an effect of criterion 8 or more at a treatment concentration of 50 ppm. [Industrial Applicability]

[0114] The compound represented by formula (I) or a salt thereof of the present invention has excellent effects as an agricultural and horticultural fungicide, and therefore the present invention may contribute to the development of the agricultural chemical industry, agriculture, and related fields.

Claims

1. General formula (I) 【Chemistry 1】 In the formula, L is the following structural formula L １ , L ２ Or L ３ The structure shown is either of the following: 【Chemistry 2】 Q is, (a13) (C １ -C ６ ) an alkylsulfonyl group; (a17) R 3 (R 4 )N base; (a20) a 5- to 6-membered heterocycle or an 8- to 10-membered fused heterocycle selected from the following: 【Chemistry 3】 【Chemistry 4】 (a21) each independently represents a halogen atom, a cyano group, a nitro group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) alkoxy groups, halo(C 1 -C 6 ) alkyl groups, (C 1 -C 6 ) alkylthio groups, (C １ -C ６ ) an alkylsulfinyl group, (C １ -C ６ ) alkylsulfonyl group, R 3 (R 4 ) N group, phenyl group, (C 1 -C 6 ) alkoxycarbonyl group and R 3 (R 4 )N represents a substituted 5- or 6-membered heterocycle or a substituted 8- or 10-membered fused heterocycle having on the ring 1 to 3 substituents selected from the group consisting of carbonyl groups. R １ and R ２ are each independently, (b1) a hydrogen atom; (b3) (C １ -C ６ ) alkyl group; (b5) (C １ -C ６ ) represents an alkoxy group. R 3 and R 4 are each independently, (c1) a hydrogen atom; (c2) (C １ -C ６ ) alkyl group; (c6) (C １ -C ６ ) an alkoxy group; (c7) Halo (C １ -C ６ ) alkyl group; (c10) (C １ -C ６ ) an alkylsulfonyl group; (c14) (C １ -C ６ ) Alkoxy (C １ -C ６ ) an alkylcarbonyl group; (c20) (C １ -C ６ ) an alkylcarbonyl group; (c23) a benzoyl group; (c24) Mono ((C １ -C ６ ) alkyl) aminocarbonyl group; (c34) a formyl group; or (c35) A pyrimidinyl group. R ５ teeth, (d1) Hydrogen atom The compound or a salt thereof represented by the formula (1):

2. Q, (a13) (C １ -C ６ ) an alkylsulfonyl group; (a17) R 3 (R 4 ) N group; or (a21) each independently represents a halogen atom, a cyano group, a nitro group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) alkoxy groups, halo(C 1 -C 6 ) alkyl groups, (C 1 -C 6 ) alkylthio groups, (C １ -C ６ ) an alkylsulfinyl group, (C １ -C ６ ) alkylsulfonyl group, R 3 (R 4 ) N group, phenyl group, (C 1 -C 6 ) alkoxycarbonyl group and R 3 (R 4 ) a substituted 5- or 6-membered heterocycle or a substituted 8- or 10-membered fused heterocycle having 1 to 3 substituents on the ring selected from the group consisting of N-carbonyl groups; R １ and R ２ are each independently, (b1) a hydrogen atom; (b3) (C １ -C ６ ) alkyl group; or (b5) (C １ -C ６ ) an alkoxy group; R 3 and R 4 are each independently, (c1) a hydrogen atom; (c2) (C １ -C ６ ) alkyl group; (c6) (C １ -C ６ ) an alkoxy group; (c10) (C １ -C ６ ) an alkylsulfonyl group; (c14) (C １ -C ６ ) Alkoxy (C １ -C ６ ) an alkylcarbonyl group; (c20) (C １ -C ６ ) an alkylcarbonyl group; (c23) a benzoyl group; (c24) Mono ((C １ -C ６ ) alkyl) aminocarbonyl group; (c34) a formyl group; or (c35) a pyrimidinyl group, R ５ but, (d1) A compound or salt thereof according to claim 1, wherein the compound or salt represents a hydrogen atom.

3. Q, (a13) (C １ -C ６ ) an alkylsulfonyl group; (a17) R 3 (R 4 ) N group; or (a21) each independently represents a halogen atom, a cyano group, a nitro group, (C １ -C ６ ) alkyl group, (C １ -C ６ ) alkoxy groups, halo(C 1 -C 6 ) alkyl groups, (C 1 -C 6 ) alkylthio groups, (C １ -C ６ ) an alkylsulfinyl group, (C １ -C ６ ) alkylsulfonyl group, R 3 (R 4 ) N group, phenyl group, (C 1 -C 6 ) alkoxycarbonyl group and R 3 (R 4 ) a substituted 5- or 6-membered heterocycle or a substituted 8- or 10-membered fused heterocycle having 1 to 3 substituents on the ring selected from the group consisting of N-carbonyl groups; R 3 and R 4 are each independently, (c1) a hydrogen atom; (c2) (C １ -C ６ ) alkyl group; (c10) (C １ -C ６ ) an alkylsulfonyl group; (c14) (C １ -C ６ ) Alkoxy (C １ -C ６ ) an alkylcarbonyl group; (c20) (C １ -C ６ ) an alkylcarbonyl group; (c23) a benzoyl group; (c24) Mono ((C １ -C ６ ) alkyl) aminocarbonyl group; (c34) a formyl group; or (c35) a pyrimidinyl group, R ５ but, The compound or salt thereof according to claim 1 or 2, wherein (d1) represents a hydrogen atom.

4. A fungicide comprising the compound or salt thereof according to any one of claims 1 to 3 as an active ingredient.

5. A method for controlling plant diseases, which comprises applying an effective amount of the fungicide according to claim 4 to plants or soil.

6. 4. Use of the compound or a salt thereof according to any one of claims 1 to 3 as a fungicide.

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