Amide compound or salt thereof, agricultural and horticultural microbicide containing said compound or salt, and method for using said microbicide

Abstract

Provided is an excellent novel agricultural and horticultural microbicide.　The present invention relates to a compound represented by general formula [I] or a salt thereof, as well as an agricultural and horticultural microbicide containing the same as an active ingredient and a method for using the microbicide.

Description

Amide compounds or salts thereof, agricultural and horticultural fungicides containing these compounds, and methods of using the same

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

[0002] Various compounds have been investigated as agricultural and horticultural fungicides, and it has been reported that certain amide compounds are useful as insecticides, fungicides, and immunomodulators (see, for example, Patent Document 1 and Non-Patent Document 1). However, these documents do not disclose the amide compound of the present invention.

[0003] WO2001011965 Pamphlet

[0004] Chinese Journal of Structural Chemistry, 28(8), 990-994, 2009

[0005] In agricultural and horticultural crop production, damage caused by various diseases and the like remains significant, and the development of new agricultural and horticultural fungicides is desired due to factors such as the development of drug resistance to existing fungicides. Furthermore, in recent years, from the perspectives of labor-saving and automated machine application, there has been a demand for the development of fungicides with properties that can withstand various application methods, such as seed treatment, low-volume application, and topical application, i.e., fungicides with appropriate stability in heat and the environment and appropriate migration and diffusion within and near crops. Meanwhile, in order to achieve sustainable agriculture, various toxicities and effects on surrounding organisms and the environment must be checked from various perspectives, and fungicides with various safety characteristics, appropriate residual ranges, biodegradability, environmental decomposition, etc. are required.

[0006] As a result of intensive studies to solve the above problems, the present inventors have found that the amide compound represented by the general formula [I] or a salt thereof has an excellent control effect against plant diseases that are problematic in the agricultural and horticultural fields. After further studies, the present inventors have found that the amide compound or a salt thereof of the present invention is suitable for various application modes of chemicals and has excellent physical, chemical, and biological properties, and have thus completed the present invention.

[0007] That is, the present invention provides: [1] a compound represented by general formula [I] {In the formula, R１(a1) a (C4-C6) alkyl group; (a2) an iodine atom; (a3) ​​a (C3-C6) alkoxy group; (a4) a halo(C1-C6) alkoxy group; (a5) a (C1-C6) alkylsulfanyl group; (a6) a halo(C1-C6) alkylsulfanyl group; (a7) an aminocarbonyl group; (a8) a Z aminocarbonyl group; (a9) a nitro group; (a10) a cyano group; (a11) a (C1-C6) alkylcarbonyl group; (a12) a Z carbonyl group; (a13) a Z group; (a14) a (C1-C12) alkylsilyl group; (a15) a Z oxy group; (a16) a hydroxy group; (a17) a (C3-C6) cycloalkoxy group; (a18) a halo(C1-C6) alkyl group; (a19) Z carbonyloxy group; (a20) Z amino group; (a21) Z alkyl group; (a22) (C2-C6) alkenyl group; (a23) halo(C2-C6) alkenyl group; (a24) (C2-C6) alkynyl group; (a25) halo(C2-C6) alkynyl group; (a26) (C3-C6) cycloalkyl group; (a27) (C3-C6) cycloalkenyl group; (a28) halo(C3-C6) cycloalkyl group; (a29) (C3-C6) cycloalkyl(C1-C6) alkyl group; (a30) (C3-C6) cycloalkyl(C3-C6) cycloalkyl group; (a31) halo(C3-C6) cycloalkyl(C1-C6) alkyl group; (a32) (a33) a halo(C1-C6)alkylsulfinyl group; (a34) a (C1-C6)alkylsulfonyl group; (a35) a halo(C1-C6)alkylsulfonyl group; (a36) a halo(C3-C6)cycloalkylhalo(C1-C6)alkyl group; or (a37) a methoxy group, and Z is (b1) a phenyl group;(b2) A halogen atom, a nitro group, a cyano group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, a halo(C1-C6)alkoxy group, a (C2-C6)alkenyl group, a halo(C2-C6)alkenyl group, a (C2-C6)alkynyl group, a (C3-C6)cycloalkyl group, a (C2-C6)alkenyloxy group, a halo(C2-C6)alkenyloxy group, a (C1-C6)alkylsulfanyl group, a halo(C1-C6)alkylsulfanyl group, a (C1-C6)alkylsulfonyloxy group, a halo(C1-C6)alkylsulfonyloxy group, a (C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylsulfonyl group, a (C2-C 6) a substituted phenyl group having 1 to 5 substituents independently selected from the group consisting of an alkenylsulfanyl group, a halo(C2-C6)alkenylsulfanyl group, a (C2-C6)alkenylsulfinyl group, a halo(C2-C6)alkenylsulfinyl group, a (C2-C6)alkenylsulfonyl group, a halo(C2-C6)alkenylsulfonyl group, an N-mono(C1-C6)alkylamino group, an N,N-di(C1-C6)alkylamino group in which the alkyl groups may be the same or different, a (C1-C6)alkylsulfonylamino group, a halo(C1-C6)alkylsulfonylamino group, a (C1-C6)alkylcarbonyl group, a halo(C1-C6)alkylcarbonyl group, a (C1-C6)alkoxycarbonyl group, a (C1-C9)alkylsilyl group, and a phenyl group; (b3) a heterocyclic group; or (b4) a substituted heterocyclic group having 1 to 3 substituents independently selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, a halo(C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkoxy group, a (C1-C6) alkylsulfanyl group, a halo(C1-C6) alkylsulfanyl group, a (C1-C6) alkylsulfinyl group, a halo(C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, and a halo(C1-C6) alkylsulfonyl group, ２(c1) a (C3-C6)alkyl group; (c2) a halo(C2-C6)alkyl group; (c3) a (C3-C6)cycloalkyl(C1-C6)alkyl group; (c4) a cyclopentyl group; (c5) a halocyclopentyl group; (c6) a (C4-C6)alkenyl group; (c7) a hydroxy(C3-C6)alkyl group; (c8) a (C1-C6)alkoxy(C1-C6)alkyl group; (c9) a halo(C1-C6)alkoxy(C1-C6)alkyl group; (c10) a (C3-C6)cycloalkoxy(C1-C6)alkyl group; (c11) a halo(C3-C6)cycloalkoxy(C1-C6)alkyl group; or (c12) a (C1-C6)alkoxy(C1-C6)alkoxy group, and R ３ (d1) a (C1-C6) alkyl group; (d2) a halogen atom; (d3) a halo(C1-C6) alkyl group; (d4) a (C1-C6) alkoxy group; (d5) a halo(C1-C6) alkoxy group; (d6) a cyano group; or (d7) a Z group, or two R ３ are bonded to each other to form a group of the following formula R ３－１ or R ３－２ may form a ring structure represented by X represents an oxygen atom or a sulfur atom, Ar １ represents a phenyl group, a pyrimidinyl group, or a pyridyl group, Ar ２ represents a pyridyl group or a quinolyl group, m represents 1, 2, 3, 4 or 5, and n represents 0, 1, 2, 3, 4 or 5, or a salt thereof.

[0008] [2] R １(a1) a (C4-C6) alkyl group; (a2) an iodine atom; (a3) ​​a (C3-C6) alkoxy group; (a4) a halo(C1-C6) alkoxy group; (a5) a (C1-C6) alkylsulfanyl group; (a6) a halo(C1-C6) alkylsulfanyl group; (a11) a (C1-C6) alkylcarbonyl group; (a12) a Z carbonyl group; (a13) a Z group; (a14) a (C1-C12) alkylsilyl group; (a15) a Z oxy group; (a16) a hydroxy group; (a17) a (C3-C6) cycloalkoxy group; (a18) a halo(C1-C6) alkyl group; (a19) a Z carbonyloxy group; (a20) a Z amino group; (a21) a Z alkyl group; (a22) (a24) a (C2-C6) alkenyl group; (a26) a (C3-C6) cycloalkyl group; (a32) a (C1-C6) alkylsulfinyl group; (a34) a (C1-C6) alkylsulfonyl group; or (a37) a methoxy group, and R ２ (c1) a (C3-C6)alkyl group; (c2) a halo(C2-C6)alkyl group; (c3) a (C3-C6)cycloalkyl(C1-C6)alkyl group; (c4) a cyclopentyl group; (c6) a (C4-C6)alkenyl group; (c7) a hydroxy(C3-C6)alkyl group; or (c8) a (C1-C6)alkoxy(C1-C6)alkyl group; and R ３ (d1) a (C1-C6) alkyl group; (d2) a halogen atom; (d3) a halo(C1-C6) alkyl group; (d4) a (C1-C6) alkoxy group; (d5) a halo(C1-C6) alkoxy group; (d6) a cyano group; or (d7) a Z group, or ３ are bonded to each other to form a group of the following formula R ３－２ may form a ring structure represented by The compound or salt thereof according to [1].

[0009] [3] R １(a1) a (C4-C6) alkyl group; (a2) an iodine atom; (a3) ​​a (C3-C6) alkoxy group; (a4) a halo(C1-C6) alkoxy group; (a6) a halo(C1-C6) alkylsulfanyl group; (a11) a (C1-C6) alkylcarbonyl group; (a12) a Z carbonyl group; (a13) a Z group; (a14) a (C1-C12) alkylsilyl group; (a15) a Z oxy group; (a17) a (C3-C6) cycloalkoxy group; (a21) a Z alkyl group; or (a37) a methoxy group, and R ２ (c1) a (C3-C6)alkyl group; (c2) a halo(C2-C6)alkyl group; (c3) a (C3-C6)cycloalkyl(C1-C6)alkyl group; (c6) a (C4-C6)alkenyl group; or (c7) a hydroxy(C3-C6)alkyl group, and R ３ (d1) a (C1-C6) alkyl group; or (d2) a halogen atom, or two R ３ are bonded to each other to form a group of the following formula R ３－２ may form a ring structure represented by X is an oxygen atom, Ar １ is a phenyl group or a pyrimidinyl group, and Ar ２ is a pyridyl group,

[0010] [3A] The compound or salt thereof according to any one of [1] to [3], wherein Z is (b1) a phenyl group; (b2) a substituted phenyl group having on the ring 1 to 5 substituents independently selected from the group consisting of halogen atoms and (C1-C6) alkyl groups; or (b4-1) a substituted 5- or 6-membered aromatic heterocyclic group having on the ring 1 to 3 substituents independently selected from the group consisting of (C1-C6) alkyl groups and halo(C1-C6) alkyl groups (preferably a substituted 5- or 6-membered N-containing aromatic heterocyclic group, particularly preferably a substituted pyrrolyl group or a substituted pyrazolyl group).

[0011] [4] An agricultural and horticultural fungicide comprising the compound described in [1] above or a salt thereof as an active ingredient, [5] An agricultural and horticultural fungicide comprising the compound described in [2] above or a salt thereof as an active ingredient, [6] An agricultural and horticultural fungicide comprising the compound described in [3] above or a salt thereof as an active ingredient, [7] An agricultural and horticultural plant disease control agent comprising the compound described in [1] above or a salt thereof as an active ingredient, [8] An agricultural and horticultural plant disease control agent comprising the compound described in [2] above or a salt thereof as an active ingredient, [9] An agricultural and horticultural plant disease control agent comprising the compound described in [3] above or a salt thereof as an active ingredient,

[10] A method for controlling plant diseases comprising treating plants or soil with an effective amount of the agricultural and horticultural fungicide described in [4] above,

[11] A method for controlling plant diseases comprising treating plants or soil with an effective amount of the agricultural and horticultural fungicide described in [5] above,

[12] A method for controlling plant diseases, comprising treating plants or soil with an effective amount of the agricultural and horticultural fungicide according to [6] above;

[13] A method for controlling plant diseases, comprising treating plants or soil with an effective amount of the agricultural and horticultural plant disease control agent according to [7] above;

[14] A method for controlling plant diseases, comprising treating plants or soil with an effective amount of the agricultural and horticultural plant disease control agent according to [8] above;

[15] A method for controlling plant diseases, comprising treating plants or soil with an effective amount of the agricultural and horticultural plant disease control agent according to [9] above;

[16] Use of the compound or a salt thereof according to [1] above as a fungicide;

[17] Use of the compound or a salt thereof according to [2] above as a fungicide;

[18] Use of the compound or a salt thereof according to [3] above as a fungicide;

[19] Use of the compound or a salt thereof according to [1] above as an agricultural and horticultural fungicide;

[20] Use of the compound or a salt thereof according to [2] above as an agricultural and horticultural fungicide.

[21] Use of the compound or salt thereof according to the above [3] as an agricultural and horticultural fungicide.

[0012] The amide compound or salt thereof of the present invention has excellent effects as an agricultural and horticultural fungicide, and is particularly effective against Chinese cabbage black spot, tomato late blight, cucumber gray mold, cucumber anthracnose, rice blast, apple scab, barley powdery mildew, wheat leaf blight, cucumber sclerotinia rot, apple ring spot, grape late rot, soybean acute blight, wheat head blight, cruciferous sclerotinia rot, and rice southern leaf blight.

[0013] In the definition of the general formula [I] of the amide compound or salt thereof of the present invention, "halo" means a "halogen atom" and represents a chlorine atom, a bromine atom, an iodine atom, or a fluorine atom.

[0014] Examples of the "(C1-C6) alkyl group" include a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, an isobutyl group, a secondary butyl group, a tertiary butyl group, a normal pentyl group, an isopentyl group, a tertiary pentyl group, a neopentyl group, a 2,3-dimethylpropyl group, a 1-ethylpropyl group, a 1-methylbutyl group, a 2-methylbutyl group, a normal hexyl group, an isohexyl group, a 2-hexyl group, a 3-hexyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 1,1,2-trimethylpentyl group, a 2,3 ... The term "(C2-C6) alkyl group" refers to a linear or branched alkyl group having 1 to 6 carbon atoms, such as a methylpropyl group or a 3,3-dimethylbutyl group, and examples of the term "(C2-C6) alkyl group" include an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, an isobutyl group, a secondary butyl group, a tertiary butyl group, a normal pentyl group, an isopentyl group, a tertiary pentyl group, a neopentyl group, a 2,3-dimethylpropyl group, a 1-ethylpropyl group, a 1-methylbutyl group, a 2-methylbutyl group, a normal hexyl group, an isohexyl group, a 2,3-dimethylpropyl group, a 1-ethylpropyl group, a 1-methylbutyl group, a 2-methylbutyl group, a normal hexyl group, an isohexyl group, a 2,3-dimethylbutyl ... The term "(C3-C6) alkyl group" refers to a straight-chain or branched-chain alkyl group having 2 to 6 carbon atoms, such as a 3-hexyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 1,1,2-trimethylpropyl group, or a 3,3-dimethylbutyl group. Examples of the "(C3-C6) alkyl group" include a normal propyl group, an isopropyl group, a normal butyl group, an isobutyl group, a secondary butyl group, a tertiary butyl group, a normal pentyl group, an isopentyl group, a tertiary pentyl group, a neopentyl group, a 2,3-dimethylpropyl group, and a 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, 3,3-dimethylbutyl group, etc., and "(C4-C6) alkyl group" refers to, for example, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group, tertiary pentyl group, neopentyl group, 2,It refers to a linear or branched alkyl group having 4 to 6 carbon atoms, such as a 3-dimethylpropyl group, a 1-ethylpropyl group, a 1-methylbutyl group, a 2-methylbutyl group, a normal hexyl group, an isohexyl group, a 2-hexyl group, a 3-hexyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 1,1,2-trimethylpropyl group, or a 3,3-dimethylbutyl group; and "(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 "(C4-C6) alkenyl group" refers to a linear or branched alkenyl group having 4 to 6 carbon atoms, such as 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, and the term "(C2-C6) alkynyl group" refers to a linear or branched 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.

[0015] 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; the "(C3-C6) cycloalkenyl group" refers to a cyclic alkenyl group having 3 to 6 carbon atoms, such as a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, or a cyclohexyl group; the "(C1-C6) alkoxy group" refers to, for example, 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, a 1,1,2-trimethyl The "(C3-C6)alkoxy group" refers to a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms, such as a normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyloxy group, tertiary pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normal hexyloxy group, isohexyloxy group, or 1,1,2-trimethylpropyloxy group, and the "(C3-C6)cycloalkoxy group" refers to a cyclic alkoxy group having 3 to 6 carbon atoms, such as a cyclopropyloxy group, cyclobutyloxy group, cyclopropyloxy group, or cyclobutyloxy group.

[0016] The "(C2-C6) alkenyloxy group" refers to a linear or branched alkenyloxy group having 2 to 6 carbon atoms, such as a propenyloxy group, a butenyloxy group, a pentenyloxy group, or a hexenyloxy group, and the "(C2-C6) alkynyloxy group" refers to a linear or branched alkynyloxy group having 2 to 6 carbon atoms, such as a propynyloxy group, a butynyloxy group, a pentynyloxy group, or a hexynyloxy group.

[0017] Examples of the "(C1-C6) alkylsulfanyl group" include a methylsulfanyl group, an ethylsulfanyl group, a normal propylsulfanyl group, an isopropylsulfanyl group, a normal butylsulfanyl group, a secondary butylsulfanyl group, a tertiary butylsulfanyl group, a normal pentylsulfanyl group, an isopentylsulfanyl group, a tertiary pentylsulfanyl group, a neopentylsulfanyl group, a 2,3-dimethylpropylsulfanyl group, a 1-ethylpropylsulfanyl group, a 1-methylbutylsulfanyl group, It refers to a linear or branched alkylsulfanyl group having 1 to 6 carbon atoms, such as a normal hexylsulfanyl group, an isohexylsulfanyl group, or a 1,1,2-trimethylpropylsulfanyl group. Examples of the "(C1-C6) alkylsulfinyl group" include a methylsulfinyl group, an ethylsulfinyl group, a normal propylsulfinyl group, an isopropylsulfinyl group, a normal butylsulfinyl group, a secondary butylsulfinyl group, a tertiary butylsulfinyl group, a normal pentylsulfinyl group, and an isopentylsulfinyl group. The term "(C1-C6) alkylsulfonyl group" refers to a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as a tertiary pentylsulfinyl group, a neopentylsulfinyl group, a 2,3-dimethylpropylsulfinyl group, a 1-ethylpropylsulfinyl group, a 1-methylbutylsulfinyl group, a normal hexylsulfinyl group, an isohexylsulfinyl group, or a 1,1,2-trimethylpropylsulfinyl group. Examples of the "(C1-C6) alkylsulfonyl group" include a methylsulfonyl group, an ethylsulfonyl group, a normal propylsulfonyl group, an isopropylsulfonyl group, and the like. and 1,1,2-trimethylpropylsulfonyl groups, such as a butyl group, a normal butylsulfonyl group, a secondary butylsulfonyl group, a tertiary butylsulfonyl group, a normal pentylsulfonyl group, an isopentylsulfonyl group, a tertiary pentylsulfonyl group, a neopentylsulfonyl group, a 2,3-dimethylpropylsulfonyl group, a 1-ethylpropylsulfonyl group, a 1-methylbutylsulfonyl group, a normal hexylsulfonyl group, an isohexylsulfonyl group, or a 1,1,2-trimethylpropylsulfonyl group.

[0018] The "(C2-C6) alkenylsulfanyl group" refers to a linear or branched alkenylsulfanyl group having 2 to 6 carbon atoms, such as a vinylsulfanyl group, an allylsulfanyl group, an isopropenylsulfanyl group, a 1-butenylsulfanyl group, a 2-butenylsulfanyl group, a 2-methyl-2-propenylsulfanyl group, a 1-methyl-2-propenylsulfanyl group, a 2-methyl-1-propenylsulfanyl group, a pentenylsulfanyl group, a 1-hexenylsulfanyl group, or a 3,3-dimethyl-1-butenylsulfanyl group. The "(C2-C6) alkenylsulfinyl group" refers to a vinylsulfinyl group, an allylsulfinyl group, an isopropenylsulfinyl group, a 1-butenylsulfinyl group, a 2-butenylsulfinyl group, a 2-methyl-2-propenylsulfinyl group, a 1-hexenylsulfanyl group, or a 3,3-dimethyl-1-butenylsulfanyl group. and the like. A "(C2-C6) alkenylsulfonyl group" refers to a straight-chain or branched-chain alkenylsulfonyl group having 2 to 6 carbon atoms, such as a vinylsulfonyl group, a 2-methyl-1-propenylsulfinyl group, a pentenylsulfinyl group, a 1-hexenylsulfinyl group, or a 3,3-dimethyl-1-butenylsulfinyl group. A "(C2-C6) alkenylsulfonyl group" refers to a straight-chain or branched-chain alkenylsulfonyl group having 2 to 6 carbon atoms, such as a vinylsulfonyl group, an allylsulfonyl group, an isopropenylsulfonyl group, a 1-butenylsulfonyl group, a 2-butenylsulfonyl group, a 2-methyl-2-propenylsulfonyl group, a 1-methyl-2-propenylsulfonyl group, a 2-methyl-1-propenylsulfonyl group, a pentenylsulfonyl group, a 1-hexenylsulfonyl group, or a 3,3-dimethyl-1-butenylsulfonyl group.

[0019] The term "hydroxy(C3-C6) alkyl group" refers to a straight-chain or branched-chain alkyl group having 3 to 6 carbon atoms substituted with hydroxy, such as a 2-hydroxypropyl group, a 2-hydroxy-2-methyl-propyl group, or the like.

[0020] 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, or a hexanoyl group.

[0021] 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, an ethoxycarbonyl group, a normal propoxycarbonyl group, an isopropoxycarbonyl group, a normal butoxycarbonyl group, an isobutoxycarbonyl group, a secondary butoxycarbonyl group, a tertiary butoxycarbonyl group, or a pentyloxycarbonyl group.

[0022] The "(C1-C6) alkylsulfonyloxy group" refers to a linear or branched alkylsulfonyloxy group having 1 to 6 carbon atoms, such as a methylsulfonyloxy group, ethylsulfonyloxy group, normal propylsulfonyloxy group, isopropylsulfonyloxy group, normal butylsulfonyloxy group, secondary butylsulfonyloxy group, tertiary butylsulfonyloxy group, normal pentylsulfonyloxy group, isopentylsulfonyloxy group, tertiary pentylsulfonyloxy group, neopentylsulfonyloxy group, 2,3-dimethylpropylsulfonyloxy group, 1-ethylpropylsulfonyloxy group, 1-methylbutylsulfonyloxy group, normal hexylsulfonyloxy group, isohexylsulfonyloxy group, or 1,1,2-trimethylpropylsulfonyloxy group. The "(C1-C6) alkylsulfonylamino group" refers to an alkylsulfonylamino group having a (C1-C6) alkyl group, such as a methylsulfonylamino group, ethylsulfonylamino group, normal propylsulfonylamino group, isopropylsulfonylamino group, normal butylsulfonylamino group, secondary butylsulfonylamino group, tertiary butylsulfonylamino group, normal pentylsulfonylamino group, isopentylsulfonylamino group, tertiary pentylsulfonylamino group, neopentylsulfonylamino group, 2,3-dimethylpropylsulfonylamino group, 1-ethylpropylsulfonylamino group, 1-methylbutylsulfonylamino group, normal hexylsulfonylamino group, isohexylsulfonylamino group, or 1,1,2-trimethylpropylsulfonylamino group.

[0023] The above "(C1-C6) alkyl group" (including "(C2-C6) alkyl group", "(C3-C6) alkyl group", and "(C4-C6) alkyl group"), "(C2-C6) alkenyl group" (including "(C4-C6) alkenyl group"), "(C2-C6) alkynyl group", "(C3-C6) cycloalkyl group" (including "cyclopentyl group"), "(C1-C6) alkoxy group" (including "(C3-C6) alkoxy group"), "(C3-C6) cycloalkoxy group", "(C2-C6) alkenyloxy group", and "(C1-C6) alkylsulfanyl group" ", "(C1-C6) alkylsulfinyl group", "(C1-C6) alkylsulfonyl group", "(C1-C6) alkylsulfonyloxy group", "(C2-C6) alkenylsulfanyl group", "(C2-C6) alkenylsulfinyl group", "(C2-C6) alkenylsulfonyl group", "(C1-C6) alkylsulfonylamino group", and "(C1-C6) alkylcarbonyl 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.

[0024] The above-mentioned "substituents substituted with one or more halogen atoms at substitutable positions" are respectively "halo(C1-C6)alkyl groups", "halo(C2-C6)alkenyl groups", "halo(C2-C6)alkynyl groups", "halo(C3-C6)cycloalkyl groups", "halo(C1-C6)alkoxy groups", "halo(C3-C6)cycloalkoxy groups", "halo(C2-C6)alkenyloxy groups", and "halo(C1-C6)alkylsulfanyl groups". group," "halo(C1-C6)alkylsulfinyl group," "halo(C1-C6)alkylsulfonyl group," "halo(C1-C6)alkylsulfonyloxy group," "halo(C2-C6)alkenylsulfanyl group," "halo(C2-C6)alkenylsulfinyl group," "halo(C2-C6)alkenylsulfonyl group," "halo(C1-C6)alkylsulfonylamino group," or "halo(C1-C6)alkylcarbonyl group."

[0025] Examples of the "halo(C1-C6)alkyl group" include a fluoromethyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a trichloromethyl group, a 2-fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a heptafluoropropyl group, and a heptafluoroisopropyl group.

[0026] Examples of the "halo(C2-C6)alkenyl group" include a 2-fluorovinyl group, a 3-chloroallyl group, a 2,2-dichloro-1-methylethenyl group, and a 2,3,3-trichloro-1-methyl-2-propenyl group.

[0027] Examples of the "halo(C2-C6)alkynyl group" include a 3-chloro-2-propynyl group and a 3-chloro-1,1-dimethyl-2-propynyl group.

[0028] Examples of the "halo(C3-C6)cycloalkyl group" include a 2-fluorocyclopropyl group, a 2-chlorocyclopropyl group, a 2-iodocyclopropyl group, a 1,2-difluorocyclopropyl group, a 2,2-difluorocyclopropyl group, a 2-chloro-3-fluorocyclopropyl group, and a 1,2,2,3,3-pentachlorocyclopropyl group.

[0029] Examples of the "halo(C1-C6)alkoxy group" include a fluoromethoxy group, a chloromethoxy group, a bromomethoxy group, an iodomethoxy group, a difluoromethoxy group, a dichloromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a trichloromethoxy group, a 2-fluoroethoxy group, a 2-chloroethoxy group, a 2-bromoethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a pentafluoroethoxy group, a heptafluoropropyloxy group, and a heptafluoroisopropyloxy group.

[0030] Examples of the "halo(C3-C6)cycloalkoxy group" include a 2-fluorocyclopropyloxy group, a 2-chlorocyclopropyloxy group, a 2-iodocyclopropyloxy group, a 1,2-difluorocyclopropyloxy group, a 2,2-difluorocyclopropyloxy group, a 2-chloro-3-fluorocyclopropyloxy group, and a 1,2,2,3,3-pentachlorocyclopropyloxy group.

[0031] Examples of the "halo(C2-C6)alkenyloxy group" include a 2-fluorovinyloxy group, a 3-chloroallyloxy group, a 2,2-dichloro-1-methylethenyloxy group, and a 2,3,3-trichloro-1-methyl-2-propenyloxy group.

[0032] Examples of the "halo(C1-C6)alkylsulfanyl group" include a fluoromethylsulfanyl group, a 2-fluoroethylsulfanyl group, a 3-fluoro-n-propylsulfanyl group, a (2,2-difluoro-1-methylethyl)sulfanyl group, and a (2,2,2-trichloro-1-methylethyl)sulfanyl group.

[0033] Examples of the "halo(C1-C6)alkylsulfinyl group" include a fluoromethylsulfinyl group, a 2-fluoroethylsulfinyl group, a 3-fluoro-n-propylsulfinyl group, a (2,2-difluoro-1-methylethyl)sulfinyl group, and a (2,2,2-trichloro-1-methylethyl)sulfinyl group.

[0034] Examples of the "halo(C1-C6)alkylsulfonyl group" include a fluoromethylsulfonyl group, a 2-fluoroethylsulfonyl group, a 3-fluoro-n-propylsulfonyl group, a (2,2-difluoro-1-methylethyl)sulfonyl group, and a (2,2,2-trichloro-1-methylethyl)sulfonyl group.

[0035] Examples of the "halo(C1-C6)alkylsulfonyloxy group" include a fluoromethylsulfonyloxy group, a 2-fluoroethylsulfonyloxy group, a 3-fluoro-n-propylsulfonyloxy group, a (2,2-difluoro-1-methylethyl)sulfonyloxy group, and a (2,2,2-trichloro-1-methylethyl)sulfonyloxy group.

[0036] Examples of the "halo(C2-C6)alkenylsulfanyl group" include a 2-fluorovinylsulfanyl group, a 3-chloroallylsulfanyl group, a 2,2-dichloro-1-methylethenylsulfanyl group, and a 2,3,3-trichloro-1-methyl-2-propenylsulfanyl group.

[0037] Examples of the "halo(C2-C6)alkenylsulfinyl group" include a 2-fluorovinylsulfinyl group, a 3-chloroallylsulfinyl group, a 2,2-dichloro-1-methylethenylsulfinyl group, and a 2,3,3-trichloro-1-methyl-2-propenylsulfinyl group.

[0038] Examples of the "halo(C2-C6)alkenylsulfonyl group" include a 2-fluorovinylsulfonyl group, a 3-chloroallylsulfonyl group, a 2,2-dichloro-1-methylethenylsulfonyl group, and a 2,3,3-trichloro-1-methyl-2-propenylsulfonyl group.

[0039] Examples of the "halo(C1-C6)alkylsulfonylamino group" include a 2-fluorovinylsulfonylamino group, a 3-chloroallylsulfonylamino group, a 2,2-dichloro-1-methylethenylsulfonylamino group, and a 2,3,3-trichloro-1-methyl-2-propenylsulfonylamino group.

[0040] Examples of the "halo(C1-C6)alkylcarbonyl group" include a fluoroacetyl group, a chloroacetyl group, a bromoacetyl group, an iodoacetyl group, a difluoroacetyl group, a dichloroacetyl group, a trifluoroacetyl group, a chlorodifluoroacetyl group, a bromodifluoroacetyl group, a trichloroacetyl group, a 2-fluoropropanoyl group, a 2-chloropropanoyl group, a 2-bromopropanoyl group, a 2,2-difluoropropanoyl group, a 2,2,2-trifluoropropanoyl group, a pentafluoropropanoyl group, a heptafluorobutanoyl group, and a heptafluoroisobutanoyl group.

[0041] Examples of the "N-mono(C1-C6)alkylamino group" include alkylamino groups having a linear or branched alkyl group of 1 to 6 carbon atoms, such as N-methylamino, N-ethylamino, and N-isopropylamino. Examples of the "N-mono(C2-C6)alkenylamino group" include alkenylamino groups having a linear or branched alkenyl group of 2 to 6 carbon atoms, such as N-ethenylamino, N-propenylamino, and N-(1-methyl-2-propen-1-yl)amino. Examples of the "N-mono(C2-C6)alkynylamino group" include alkynylamino groups having a linear or branched alkynyl group of 2 to 6 carbon atoms, such as N-ethynylamino and N-2-propynylamino.

[0042] Examples of the "N,N-di(C1-C6)alkylamino group, in which the alkyl groups may be the same or different" include a dialkylamino group having 2 to 12 carbon atoms and having a linear or branched alkyl group having 1 to 6 carbon atoms, such as an N,N-dimethylamino group or an N-ethyl-N-methylamino group.

[0043] Expressions such as "(C1-C6)", "(C1-C10)", "(C2-C6)", "(C3-C6)", and "(C3-C7)" indicate the range of carbon atoms in various substituents. Furthermore, the above definitions can also be applied to groups to which the above substituents are linked. For example, "(C1-C6)alkoxy(C1-C6)alkyl" 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.

[0044] Examples of the "heterocyclic group" and "heterocycle" include a 5- or 6-membered monocyclic aromatic heterocyclic group or a 4- or 6-membered monocyclic non-aromatic heterocyclic group containing, as ring-constituting atoms other than carbon atoms, 1 to 4 heteroatoms selected from oxygen atoms, sulfur atoms, and nitrogen atoms.

[0045] Examples of the "aromatic heterocyclic group" include furyl, thienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, triazinyl, indolyl, indazolyl, benzimidazolyl, azaindolyl, azaindazolyl, benzofuranyl, benzothiophenyl, and benzisoxazolyl. and monocyclic aromatic heterocyclic groups or condensed polycyclic heterocyclic groups such as benzisothiazolyl, benzoxazolyl, benzothiazolyl, benzothiadiazolyl, quinolyl, quinolidinyl, quinoxalinyl, phthalazinyl, quinazolinyl, cinnolinyl, naphthyridinyl, pyridopyrimidinyl, pyridopyrazinyl, benzopyranyl, benzoxazinyl, carbazolyl, dibenzofuranyl, acridinyl, phenazinyl, phenothiazinyl, and phenoxathiinyl.

[0046] Examples of the "non-aromatic heterocyclic group" include oxetanyl, thietanyl, azetidinyl, pyrrolidinyl, piperidyl, morpholinyl, thiomorpholinyl, piperazinyl, hexamethyleneiminyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, oxazolinyl, thiazolinyl, isoxazolinyl, imidazolinyl, dioxolyl, dioxolanyl, dihydrooxadiazolyl, 2-oxo-pyrrolidin-1-yl, 2-oxo-1,3-oxazolidin-5-yl, 5-oxo-1,2,4-oxadiazolin-3-yl, 1,3-dioxolan-2-yl, 1-oxo-1,3-oxazolidin-5-yl, 5-oxo-1,2,4-oxadiazolin-3-yl, 1,3-dioxolan-2-yl, 1-oxo-1,3-oxazolidin-5-yl, 1-oxo-1,3-oxazolidin-5-yl, 1-oxo-1,3-dioxolan-2-yl, 1-oxo-1,3-oxazolidin-5-yl, 1-oxo-1,3-dioxolan-2-yl, 1-oxo-1,3-dioxolan-2-yl, 1-oxo-1,3-dioxolan-2-yl, 1-oxo-1,3-dioxolan-2-yl, 1-oxo-1,3-dioxolan-5 ... , 3-dioxan-2-yl, 1,3-dioxepan-2-yl, pyranyl, tetrahydropyranyl, thiopyranyl, tetrahydrothiopyranyl, 1-oxidetetrahydrothiopyranyl, 1,1-dioxidetetrahydrothiopyranyl, tetrahydrofuranyl, dioxanyl, pyrazolidinyl, pyrazolinyl, tetrahydropyrimidinyl, dihydrotriazolyl, tetrahydrotriazolyl, decahydroisoquinoline, quinuclidine, azaadamantane, 8-oxa-2-azaspiro[4.5]decane, and the like.

[0047] Examples of the "(C1-C12) alkylsilyl group" include silyl groups substituted with (C1-C12) alkyl, such as TMS (trimethylsilyl), TES (triethylsilyl), TBS (tert-butyldimethylsilyl), TIPS (triisopropylsilyl), and BIBS (di-tert-butylisobutylsilyl). Examples of the "(C1-C9) alkylsilyl group" include silyl groups substituted with (C1-C9) alkyl, such as TMS (trimethylsilyl), TES (triethylsilyl), TBS (tert-butyldimethylsilyl), TIPS (triisopropylsilyl), and BIBS (di-tert-butylisobutylsilyl).

[0048] In the compound of the present invention represented by the general formula [I] (including the compounds represented by the general formulae [IA] to [IF] described later), preferred embodiments are shown below.

[0049] R １is preferably (a1) a (C4-C6) alkyl group; (a2) an iodine atom; (a3) ​​a (C3-C6) alkoxy group; (a4) a halo(C1-C6) alkoxy group; (a5) a (C1-C6) alkylsulfanyl group; (a6) a halo(C1-C6) alkylsulfanyl group; (a11) a (C1-C6) alkylcarbonyl group; (a12) a Z carbonyl group; (a13) a Z group; (a14) a (C1-C12) alkylsilyl group; (a15) a Z oxy group; (a16) a hydroxy group; (a17) a (C3-C6) cycloalkoxy group; (a18) a halo(C1-C6) alkyl group; (a19) a Z carbonyloxy group; (a20) a Z amino group; (a21) a Z alkyl group; (a22) (a24) a (C2-C6) alkenyl group; (a26) a (C3-C6) cycloalkyl group; (a32) a (C1-C6) alkylsulfinyl group; (a34) a (C1-C6) alkylsulfonyl group; or (a37) a methoxy group.

[0050] R １ is more preferably (a1) a (C4-C6) alkyl group; (a2) an iodine atom; (a3) ​​a (C3-C6) alkoxy group; (a4) a halo(C1-C6) alkoxy group; (a6) a halo(C1-C6) alkylsulfanyl group; (a11) a (C1-C6) alkylcarbonyl group; (a12) a Z carbonyl group; (a13) a Z group; (a14) a (C1-C12) alkylsilyl group; (a15) a Z oxy group; (a17) a (C3-C6) cycloalkoxy group; (a21) a Z alkyl group; or (a37) a methoxy group.

[0051] In another embodiment, R １is preferably (a1) a (C4-C6) alkyl group; (a2) an iodine atom; (a3) ​​a (C3-C6) alkoxy group; (a4) a halo(C1-C6) alkoxy group; (a5) a (C1-C6) alkylsulfanyl group; (a6) a halo(C1-C6) alkylsulfanyl group; (a7) an aminocarbonyl group; (a8) a Z aminocarbonyl group; (a9) a nitro group; (a10) a cyano group; (a11) a (C1-C6) alkylcarbonyl group; (a12) a Z carbonyl group; (a13) a Z group; (a14) a (C1-C12) alkylsilyl group; (a15) a Z oxy group; (a16) a hydroxy group; (a17) a (C3-C6) cycloalkoxy group; (a18) Halo(C1-C6)alkyl group; (a19) Z carbonyloxy group; (a20) Z amino group; (a21) Z alkyl group; (a22) (C2-C6) alkenyl group; (a23) halo(C2-C6) alkenyl group; (a24) (C2-C6) alkynyl group; (a25) halo(C2-C6)alkynyl group; (a26) (C3-C6) cycloalkyl group; (a27) (C3-C6) cycloalkenyl group; (a28) halo(C3-C6)cycloalkyl group; (a29) (C3-C6) cycloalkyl(C1-C6)alkyl group; (a30) (C3-C6) cycloalkyl(C3-C6)cycloalkyl group; (a31) halo(C3-C6) cycloalkyl(C1-C6)alkyl group; (a32) a (C1-C6) alkylsulfinyl group; (a33) a halo(C1-C6) alkylsulfinyl group; (a34) a (C1-C6) alkylsulfonyl group; (a35) a halo(C1-C6) alkylsulfonyl group; or (a36) a halo(C3-C6) cycloalkylhalo(C1-C6) alkyl group.

[0052] Z is preferably (b1) a phenyl group; (b2) a substituted phenyl group having on the ring 1 to 5 substituents independently selected from the group consisting of halogen atoms and (C1-C6) alkyl groups; or (b4-1) a substituted 5- or 6-membered aromatic heterocyclic group having on the ring 1 to 3 substituents independently selected from the group consisting of (C1-C6) alkyl groups and halo(C1-C6) alkyl groups.

[0053] Z is more preferably (b1) a phenyl group; (b2) a substituted phenyl group having on the ring 1 to 5 substituents independently selected from the group consisting of halogen atoms and (C1-C6) alkyl groups; or (b4-2) a substituted 5- or 6-membered N-containing aromatic heterocyclic group having on the ring 1 to 3 substituents independently selected from the group consisting of (C1-C6) alkyl groups and halo(C1-C6) alkyl groups (preferably a substituted pyrrolyl group or a substituted pyrazolyl group).

[0054] R ２ is preferably (c1) a (C3-C6)alkyl group; (c2) a halo(C2-C6)alkyl group; (c3) a (C3-C6)cycloalkyl(C1-C6)alkyl group; (c4) a cyclopentyl group; (c6) a (C4-C6)alkenyl group; (c7) a hydroxy(C3-C6)alkyl group; or (c8) a (C1-C6)alkoxy(C1-C6)alkyl group.

[0055] R ２ is more preferably (c1) a (C3-C6) alkyl group; (c2) a halo(C2-C6) alkyl group; (c3) a (C3-C6) cycloalkyl(C1-C6) alkyl group; (c6) a (C4-C6) alkenyl group; (c7) a hydroxy(C3-C6) alkyl group; or (c8) a (C1-C6) alkoxy(C1-C6) alkyl group.

[0056] R ２is more preferably (c1) a (C3-C6) alkyl group; (c2) a halo(C2-C6) alkyl group; (c3) a (C3-C6) cycloalkyl(C1-C6) alkyl group; (c6) a (C4-C6) alkenyl group; or (c7) a hydroxy(C3-C6) alkyl group.

[0057] R ３ is preferably (d1) a (C1-C6) alkyl group; (d2) a halogen atom; (d3) a halo(C1-C6) alkyl group; (d4) a (C1-C6) alkoxy group; (d5) a halo(C1-C6) alkoxy group; (d6) a cyano group; or (d7) a Z group, or two R ３ are bonded to each other to form a group of the following formula R ３－２ A ring structure represented by the following formula may be formed.

[0058] R ３ is more preferably (d1) a (C1-C6) alkyl group; or (d2) a halogen atom, or two R ３ are bonded to each other to form a group of the following formula R ３－２ A ring structure represented by the following formula may be formed.

[0059] X is preferably an oxygen atom. １ is preferably a phenyl group or a pyrimidinyl group. １ is particularly preferably a phenyl group. ２ is preferably a pyridyl group

[0060] m is preferably 1 or 2. m is particularly preferably 1. n is preferably 0, 1 or 2.

[0061] Examples of salts of the amide compound represented by the 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.

[0062] The amide compounds and salts thereof represented by the general formula [I] of the present invention may have one or more asymmetric centers in their structural formula, and may exist as two or more optical isomers and diastereomers, and the present invention encompasses all of the optical isomers and mixtures containing them in any ratio.Furthermore, the amide compounds and salts thereof represented by the general formula [I] of the present invention may have two geometric isomers derived from a carbon-carbon double bond in their structural formula, and the present invention encompasses all of the geometric isomers and mixtures containing them in any ratio.

[0063] The amide compound represented by the general formula [I] of the present invention or a salt thereof can be produced, for example, by the following production methods, but the present invention is not limited to these. Production Method 1.

[0064] (The symbols in the formula have the same meanings as defined above.)

[0065] In this reaction, a carboxylic acid represented by general formula [1] is reacted with an amine compound represented by general formula [2] in the presence of a condensing agent, a base, and an inert solvent to produce an amide compound represented by general formula [I]. Since this reaction is an equimolar reaction, each reactant may be used in equimolar amounts, but any of the reactants may also be used in excess.

[0066] The condensing agent used in this reaction may be any one that is commonly used in the production of amides, and examples thereof include trifluoroacetic anhydride, Mukaiyama's reagent (2-chloro-N-methylpyridinium iodide), DCC (1,3-dicyclohexylcarbodiimide), CDI (carbonyldiimidazole), DEPC (diethyl cyanophosphate), etc., and the amount used may be appropriately selected from the range of equimolar to excess molar amount relative to the carboxylic acid represented by the general formula [1].

[0067] The base used in this reaction may be an inorganic base or an organic base. Examples of the inorganic base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; carbonates such as sodium carbonate, potassium carbonate and sodium hydrogencarbonate; and examples of the organic base include triethylamine, pyridine, DMAP, DBU, and the like. The amount of the base used may be selected from the range of a catalytic amount to a molar excess relative to the carboxylic acid represented by the general formula [1].

[0068] 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, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc.; chain or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, etc.; esters such as ethyl acetate, etc.; amides such as dimethylformamide, dimethylacetamide, etc.; dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, acetone, methyl ethyl ketone, etc. These inert solvents may be used alone or in combination of two or more.

[0069] This reaction can also be carried out under an atmosphere of an inert gas such as nitrogen gas or argon gas. The reaction temperature can be from room temperature to the boiling point of the inert solvent used, and the reaction time varies depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 48 hours. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by conventional methods, and the target product can be produced by purifying it by recrystallization, column chromatography, etc. as necessary. Production Method 2.

[0070] (In the formula, R １ , Ar １ and m are as defined above, and the carbon marked with * indicates an asymmetric carbon.)

[0071] Production method of step [b] In this reaction, an optically active carboxylic acid represented by general formula [5] can be produced by reacting a compound represented by general formula [3] with hydrogen in the presence of an asymmetric iridium catalyst represented by general formula [4] and a base.

[0072] This reaction can be carried out, for example, in an organic solvent (methanol, ethanol, isopropanol, benzene, toluene, etc.) by the addition of a base (triethylamine, N,N-diisopropylethylamine, etc.) and XA １ From XA ４ The reaction may be carried out in the presence of an asymmetric iridium catalyst. The amount of the asymmetric iridium catalyst used may be a catalytic amount relative to the compound represented by general formula [3]. The amount of the base used may be appropriately selected usually from the range of 0.1 to 5 times the molar amount of the compound represented by general formula [3].

[0073] This reaction is carried out by adding hydrogen gas under a pressure condition of 1 to 12 atm. The reaction temperature can be from room temperature to the boiling point of the inert solvent used. The reaction time varies depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 48 hours.

[0074] Specific examples of the compound of the present invention are shown below. In the following tables (Table 1-1, Table 1-2, Table 2-1, Table 3-1, Table 4-1, Table 5-1, Table 6-1 and Table 7-1), H represents a hydrogen atom, F represents a fluorine atom, I represents an iodine atom, and C represents a chlorine atom. Physical properties include melting point (°C), refractive index, ｎD(Measurement temperature: ° C.) or NMR data are shown, and the NMR data are shown in Appendix 1.

[0075] Examples of specific compounds represented by the following general formula [IA] are shown in the table below.

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086] Examples of specific compounds represented by the following general formula [IB] are shown in the table below.

[0087]

[0088]

[0089] Examples of specific compounds represented by the following general formula [IC] are shown in the table below.

[0090]

[0091]

[0092] Examples of specific compounds represented by the following general formula [ID] are shown in the table below.

[0093]

[0094]

[0095] Examples of specific compounds represented by the following general formula [IE] are shown in the table below.

[0096]

[0097]

[0098] Examples of specific compounds represented by the following general formula [IF] are shown in the table below.

[0099]

[0100]

[0101] Compound I-A-32 can be chromatographically separated using an appropriate chiral column. The racemic mixture was separated using a chiral column (CHIRALPAK® AS-RH (manufactured by Daicel Corporation), 4.6 mm x 150 mm, 5 μm, detector: 220 nm) at a column temperature of 35°C and a mobile phase flow rate of 1 mL / min (5 mM Ammonium Acetate in H ２ The two single enantiomers (I-G-3 and I-G-4) were separated by elution under conditions of 0 / MeCN = 400 / 600 (v / v). I-A-39 was also separated into two single enantiomers (I-G-1 and I-G-2) by using a chiral column.

[0102]

[0103]

[0104] Agricultural and horticultural fungicides containing the amide compounds of the present invention represented by the general formula [I] or salts thereof as an active ingredient are suitable for controlling diseases that occur in grains, fruit trees, vegetables, other crops and ornamental plants.

[0105] Target diseases include fungal diseases, bacterial diseases, viral diseases, etc. Examples of fungal diseases include diseases caused by imperfect fungi (e.g., diseases of the genus Botrytis, diseases of the genus Helminthosporium, diseases of the genus Fusarium, diseases of the genus Septoria, diseases of the genus Sarcospora, diseases of the genus Pseudocercosporella, diseases of the genus Rhynchosporium, diseases of the genus Pyricularia ... diseases of the genus Hemilelia, diseases of the genus Rhizoctonia, diseases of the genus Ustilago, diseases of the genus Typhula, diseases of the genus Puccinia, etc.); diseases caused by ascomycetes (for example, diseases of the genus Venturia, Venturia diseases, Podosphaera diseases, Leptosphaeria diseases, Blumeria diseases, Erysiphe diseases, Microdochium diseases, Sclerotinia diseases, Gaeumannom Examples of diseases that may be caused by fungi include diseases of the genus Pseudomonas, diseases of the genus Pythium, diseases of the genus Pythium, diseases of the genus Pyrenophora, etc.), and diseases caused by other fungi (for example, diseases of the genus Ascochyta, diseases of the genus Phoma, diseases of the genus Pythium, diseases of the genus Corticium, diseases of the genus Pyrenophora, etc.). Examples of bacterial diseases include diseases of the genus Pseudomonas, diseases of the genus Xanthomonas, diseases of the genus Erwinia, etc. Examples of viral diseases include diseases caused by tobacco mosaic virus.

[0106] Specific examples of fungal diseases include rice blast (Pyricularia oryzae), rice sheath blight (Rhizoctonia solani), rice brown spot (Cochliobolus miyabeanus), rice seedling damping-off (Rhizopus chinensis, Pythium graminicola, Fusarium graminicola, Fusarium roseum, Mucor sp., Phoma sp., Tricoderma sp.), rice bakanae disease (Gibberella fujikuroi), powdery mildew (Blumeria graminis), powdery mildew of cucumber, etc. (Sphaerotheca fuliginea), powdery mildew of eggplant, etc. (Erysiphe cichoracoarum) and powdery mildew of other host plants, eyespot disease of barley and wheat, etc. (Pseudocercosporella herpotrichoides), ear smut of wheat, etc. (Urocystis tritici), snow rot disease of barley and wheat, etc. (Microdochium nivalis, Pythium iwayamai, Typhla ishikariensis, Typhla incarnata, Sclerotinia borealis), wheat head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivalis), rust of barley and wheat, etc. (Puccinia recondita, Puccinia striiformis, Puccinia graminis), damping-off of barley and wheat, etc. (Gaeumannomyces graminis), crown rust of oats (Puccinia coronata), and rust of other plants, gray mold of cucumber, strawberry, etc. (Botrytis cinerea), Sclerotinia sclerotiorum on cucumbers and tomatoes, Phytophthora infestans on potatoes and tomatoes, and other plant diseases such as Pseudoperonospora cubensis on cucumbers.Various plant downy mildews such as grape downy mildew (Plasmopara viticola), apple scab (Venturia inaequalis), apple leaf spot (Alternaria mali), apple ring spot (Botryosphaeria berengeriana), grape late rot (Colletotrichum gloeosporioides, Colletotrichum acutatum), grape black rot (Elsinoe ampelina), pear black spot (Alternaria kikuchiana), citrus black spot (Diaporthe citri), citrus scab (Elsinoe fawcetti), cucumber anthracnose (Colletotrichum lagenarium), 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 stripe (Pyrenophora graminea), barley scald (Rhynchosporium secalis), wheat naked smut (Ustilago nuda), wheat smut (Tilletia caries), turfgrass leaf rot (Rhizoctonia solani), turfgrass dollar spot (Sclerotinia homoeocarpa), Chinese cabbage black spot (Alternaria brassicola), tomato late blight (Phytophthora infestans), cucumber gray mold (Botrytis cinerea), barley powdery mildew (Blumeria graminis f.sp. Hordei), soybean sudden blight (Fusarium virguliforme), cruciferous stem rot (Sclerotinia sclerotirum), etc.

[0107] Specific examples of bacterial diseases include those caused by the genus Pseudomonas, such as cucumber bacterial spot (Pseudomonas syringae pv. Lachrymans), tomato bacterial wilt (Pseudomonas syringae pv. Lachrymans), and rice bacterial grain blight (Pseudomonas glumae); those caused by the genus Xanthomonas, such as cabbage black rot (Xanthomonas campestris), rice bacterial leaf blight (Xanthomonas oryzae), and citrus canker (Xanthomonas citri); and those caused by the genus Erwinia, such as cabbage soft rot (Erwinia carotovora), etc.

[0108] Specific examples of viral diseases include tobacco mosaic virus.

[0109] Among these, agricultural and horticultural fungicides containing the amide compound represented by the general formula [I] of the present invention or a salt thereof as an active ingredient are effective against fungal diseases, particularly Chinese cabbage black spot (Alternaria brassicola), tomato late blight (Phytophthora infestans), cucumber gray mold (Botrytis cinerea), cucumber anthracnose (Colletotrichum lagenarium), rice blast (Pyricularia oryzae), apple scab (Venturia inaequalis), barley powdery mildew (Blumeria graminis f.sp. Hordei), wheat leaf blight (Septoria It is highly effective against Sclerotinia tritici, cucumber sclerotinia sclerotiorum, apple ring spot (Botryosphaeria berengeriana), grape late rot (Colletotrichum gloeosporioides, Colletotrichum acutatum), soybean acute blight (Fusarium virguliforme), wheat head blight (Fusarium graminearum), cruciferous sclerotinia (Sclerotinia sclerotirum), and rice brown spot (Cochliobolus miyabeanus).

[0110] Furthermore, agricultural and horticultural fungicides containing the amide compounds of the present invention represented by general formula [I] or salts thereof as an active ingredient can be used as insecticides, either alone or in combination, or in a mixture, to control various agricultural and forestry pests, horticultural pests, stored grain pests, sanitary pests, nematodes, etc. that harm paddy rice, fruit trees, vegetables, other crops, and ornamental plants. Examples of pests or nematodes include the following. Lepidoptera (Lepidoptera) pests include the green slug moth (Parasa consocia), the red shrike moth (Anomis mesogona), the swallowtail butterfly (Papilio xuthus), the azuki bean pod moth (Matsumuraeses azukivora), the azuki bean leaf moth (Ostrinia scapulalis), the African armyworm (Spodoptera exempta), the American fall webworm (Hyphantria cunea), the corn borer (Ostrinia furnacalis), the armyworm (Pseudaletia separata), the burr moth (Tinea translucens), the rush leaf moth (Bactra furfuryla), the skipper butterfly (Parnara guttata), the rice leaf moth (Marasmia exigua), the rice beetle (Parnara guttata), and the rice fall webworm (Sesamia inferens, potato leaf moth (Brachmia triannulella), bag moth (Monema flavescens), nettle looper moth (Trichoplusia ni), turmeric moth (Pleuroptya ruralis), plum geometries (Cystidia couaggaria), blue-striped silver butterfly (Lampides boeticus), Japanese hawk moth (Cephonodes hylas), cotton bollworm (Helicoverpa armigera), large hawk moth (Phalerodonta manleyi), Japanese silk moth (Eumeta japonica), banded moth (Malacosoma neustria testacea), persimmon stalk moth (Stathmopoda masinissa), persimmon leaf moth (Cuphodes diospyrosella), Japanese rice tortrix moth (Archips xylosteanus), turnip cutworm moth (Agrotissegetum, sweet potato moth (Tetramoera schistaceana), common yellow swallowtail (Papilio machaon hippocrates), yellow spotted bat (Endoclyta sinensis), silver leafminer moth (Lyonetia prunifoliella), golden leafminer moth (Phyllonorycter ringoneella), chestnut moth (Cydia kurokoi), chestnut green fruit moth (Eucoenogenes aestuosa), grapeberry moth (Lobesia botrana), black-spotted green moth (Latoia sinica), black-spotted moth (Euzophera batangensis), mulberry moth (Phalonidia mesotypa), mulberry leaf moth (Spilosoma imparilis), mulberry leaf moth (Glyphodes pyloalis), mulberry leaf moth (Olethreutes mori), brown moth (Tineola bisselliella), bat moth (Endoclyta excrescens), Japanese rice moth (Nemapogon granellus), small grass moth (Synanthedon hector), codling moth (Cydia pomonella), diamondback moth (Plutella xylostella), rice leafroller (Cnaphalocrocis medinalis), southern pink borer (Sesamia calamistis), red borer (Scirpophaga incertulas), Japanese grass moth (Pediasia teterrellus), potato tuber moth (Phthorimaea operculella), oriental moth (Stauropus fagi persimilis), beetle striped moth (Etiella zinckenella), beet armyworm (Spodoptera exigua), white-spotted bat (Palpifer sexnotata), Spodoptera mauritia, Scirpophaga innotata, Xestia c-nigrum, Spodopteradepravata, striped moth (Ephestia kuehniella), plum geometrid (Angerona prunaria), black-spotted killer moth (Clostera anastomosis), soybean looper (Pseudoplusia includens), soybean pod moth (Matsumuraeses falcana), tobacco budworm (Helicoverpa assulta), silver looper moth (Autographa nigrisigna), black cutworm moth (Agrotis ipsilon), brown tussock moth (Euproctis pseudoconspersa), smaller tea tortrix moth (Adoxophyes orana), tea leaf moth (Caloptilia theivora), tea tortrix moth (Homona magnanima), brown moth moth (Ephestia elutella), brown leaf moth moth (Eumeta minuscula), red-spotted killer moth (Clostera anachoreta, Japanese stag beetle (Heliothis maritima), Japanese bush moth (Sparganothis pilleriana), corn borer (Busseola fusca), tussock moth (Euproctis subflava), giant stag beetle (Biston robustum), tomato fruit worm (Heliothis zea), white-streaked leaf moth (Aedia leucomelas), Japanese pear moth (Narosoideus flavidorsalis), Japanese pear leaf moth (Viminia rumicis), Japanese pear leaf moth (Bucculatrix pyrivorella), Japanese pear fruit moth (Grapholita molesta), Japanese pear leaf moth (Spulerina astaurota), Japanese pear spotted moth (Ectomyelois pyrivorella), rice stem borer (Chilo suppressalis), onion leaf moth (Acrolepiopsis sapporensis), Indian meal moth (Plodia interpunctella), Hellula undalis, Japanese cereal moth (Sitotroga cerealella), Spodoptera litura, Tortricidae (Eucosmaaporema, rose moth (Acleris comariana), small black moth (Scopelodes contractus), small white tussock moth (Orgyia thyellina), fall armyworm (Spodoptera frugiperda), butterbur moth (Ostrinia zaguliaevi), two-banded grass moth (Naranga aenescens), two-banded false burrowing moth (Andraca bipunctata), grapevine clearwing moth (Paranthrene regalis), grapevine wasp (Acosmeryx castanea), grapevine leafminer (Phyllocnistis toparcha), grapevine shriveling moth (Endopiza viteana), grapevine narrow-leaved moth (Eupoecillia ambiguella), velvet bean caterpillar (Anticarsia gemmatalis), narrow-leaved gray moth (Cnephasia cinereipalpana), gypsy moth (Lymantria dispar), pine moth (Dendrolimus spectabilis), bean root moth (Leguminivora glycinivorella), bean meal moth (Maruca testulalis), bean pea leaf moth (Matsumuraeses phaseoli), bean bean leaf moth (Caloptilia soyella), citrus leafminer (Phyllocnistis citrella), bean leaf moth (Omiodes indicate), green leaf tortrix moth (Archips fuscocupreanus), three-leaved golden looper (Acanthoplusia agnata), bag moth (Bambalina sp.), peach fruit moth (Carposina niponensis), peach leafminer (Conogethes punctiferalis), peach sediments (Synanthedon sp.), peach leafminer (Lyonetia clerkella), Common swallowtail (Papilio helenus), Common yellow butterfly (Colias erate poliographus), Black-and-white butterfly (Phalera flavescens), Large brassica white (Pierisbrassicae), white butterflies such as Pieris rapae crucivora, Euproctis similis, Acrolepiopsis suzukiella, Ostrinia nubilalis, Mamestra brassicae, Ascotis selenaria, Phtheochroides clandestina, Hoshinoa adumbratana, Odonestis pruni japonensis, Triaena intermedia, Adoxophyes orana fasciata, Grapholita inopinata, Spilonota ocellana, Spilonota lechriaspis, Illiberis pruni, Argyresthia conjugella, Caloptilia zachrysa, Archips breviplicanus, Anomis flava, Pectinophora gossypiella, Notarcha derogata, Diaphania indica, Heliothis virescens, and Earias cupreoviridis.

[0111] Hemiptera (Hemiptera) pests include the green grass bug (Nezara antennata), red-striped rice bug (Stenotus rubrovittatus), red-striped rice bug (Graphosoma rubrolineatum), red-bearded green rice bug (Trigonotylus coelestialium), red-spotted leaf bug (Aeschynteles maculatus), red-spotted rice bug (Creontiades pallidifer), red-spotted rice bug (Dysdercus cingulatus), red-spotted scale bug (Chrysomphalus ficus), red-spotted scale bug (Aonidiella aurantii), and brown cicada (Graptopsaltria nigrofuscata), American long-horned stink bug (Blissusleucopterus), Icerya scale bug (Icerya purchasi), striped stink bug (Piezodorus hybneri), rice stink bug (Lagynotomus elongatus), rice yellow leafhopper (Thaia subrufa), black rice stink bug (Scotinophara lurida), thorny long-horned aphid (Sitobion ibarae), Iwasaki stink bug (Stariodes iwasakii), pale-stained scale (Aspidiotus destructor), pale-stained green rice bug (Taylorilygus pallidulus), plum horn aphid (Myzusmumecola), plum white scale (Pseudaulacaspis prunicola), pea aphid (Acyrthosiphon pisum), spider bug (Anacanthocoris striicornis), large black-spotted stink bug (Ectometopterus micantulus), large spur-spotted spotted stink bug (Eysarcoris lewisi), large leaf bug (Molipteryx fuliginosa), Japanese giant leafhopper (Cicadella viridis), red-veined aphid (Rhopalosophumrufiabdominalis), olive scale (Saissetia oleate), greenhouse whitefly (Trialeurodes vaporariorum), oak leafhopper (Aguriahana quercus), mirid bugs (Lygus spp.), Japanese citrus aphid (Euceraphis punctipennis), citrus scale (Andaspis kashicola), citrus scale (Coccus pseudomagnoliarum), oak leafbug (Cavelerius saccharivorus), chrysanthemum long-horned aphid (Galeatus spinifrons), chrysanthemum long-horned aphid (Macrosiphoniella sanborni), yellow scale (Aonidiella citrina), brown marmorated stink bug (Halyomorpha mista), Japanese oak leafbug (Stephanitis fasciicarina), kusutokashi psyllid (Trioza camphorae), spider bug (Leptocorisa chinensis), chestnut psyllid (Trioza quercicola), walnut earworm (Uhlerites latius), grape leaf hopper (Erythroneura comes), black-legged stink bug (Paromius exiguus), black rice scale (Duplaspidiotus claviger), black-striped leafhopper (Nephotettix nigropictus), black-spotted rice turtle (Halticiellus insularis), black planthopper (Perkinsiella saccharicida), black apple psyllid (Psylla malivorella), mulberry psyllid (Anomomeura mori), mulberry mealybug (Pseudococcus longispinis), Mulberry scale (Pseudaulacaspis pentagona), Mulberry cotton scale (Pulvinaria kuwacola), Green grass bug (Apolygus lucorum), Togo gourd long-legged bughemipterus), Phyllostomy aphid (Toxoptera aurantii), sugarcane mealybug (Saccharicoccus sacchari), sugarcane root aphid (Geoica lucifuga), sugarcane brown planthopper (Numata muiri), San Jose scale (Comstockaspis perniciosa), citrus snow scale (Unaspis citri), potato aphid (Aulacorthum solani), white spotted stink bug (Eysarcoris ventralis), silverleaf whitefly (Bemisia argentifolii), white leafhopper (Cicadella spectra), white-spotted scale (Aspidiotus hederae), white-spotted stink bug (Liorhyssus hyalinus), white-backed psyllid (Calophya nigridorsalis), white-backed planthopper (Sogatella furcifera), broad bean aphid (Megoura crassicauda), radish aphid (Brevicoryne brassicae), soybean aphid (Aphis glycines), Taiwan spider bug (Leptocorisa oratorius), Taiwan green leafhopper (Nephotettix virescens), Taiwan long-horned aphid (Uroeucon formosanum), tobacco leaf bug (Cyrtopeltis tennuis), tobacco whitefly (Bemisia tabaci), tea stubble scale (Lecanium persicae), black tea spot scale (Parlatoria theae), tea leaf scale (Pseudaonidia paeoniae), tea green leafhopper (Empoasca onukii), brown-winged green bug (Plautia stali), tulip root aphid (Dysaphis tulipae), tulip long-horned aphid (Macrosiphum euphorbiae), azalea leafhoppers (Stephanitis pyrioides), and hornworms (Ceroplastesceriferus), Camellia black spotted scale (Parlatoria camelliae), Green rice bug (Apolygus spinolai), Green rice leafhopper (Nephotettix cincticeps), Shiny green stink bug (Glaucias subpunctatus), Sugar beet rice bug (Orthotylus flavosparsus), Corn aphid (Rhopalosiphum maidis), Corn planthopper (Peregrinus maidis), Spiny spotted stink bug (Eysarcoris parvus), Bed bug (Cimex lectularius), Brown planthopper (Psylla abieti), Brown planthopper (Nilaparvata lugens), Pittosporum psylla (Psylla tobirae), Long-legged bug (Eurydema rugosum), Pear aphid (Schizaphis piricola), pear psylla (Psylla pyricola), pear spotted scale (Parlatoreopsis pyri), pear earworm (Stephanitis nashi), pear mealybug (Dysmicoccus wistariae), white pear scale (Lepholeucaspis japonica), pear aphid (Sappaphis piri), false radish aphid (Lipaphis erysimi), onion aphid (Neotoxoptera formosana), husk aphid (Rhopalosophum nymphaeae), rose leafhopper (Edwardsianarosae), Japanese long-legged scale (Pinnaspisaspidistrae), alder psylla (Psylla alni), alder leafhopper (Speusotettix subfusculus), alder leafhopper (Alnetoidia alneti), brown planthopper (Sogatella panicicola), long-horned rice bug (Adelphocoris lineolatus), small red spotted stink bug (Dysdercus poecilus), small black scale (Parlatoria ziziphi), small earworm (Uhleritesdebile), small brown planthopper (Laodelphax striatella), small long-legged bug (Eurydema pulchrum), small stink bug (Cletus trigonus), small two-striped long-legged butterflies (Clovia punctata), small leafhoppers (Empoasca sp.), flat-headed scale (Coccus hesperidum), flat-headed long-legged bug (Pachybrachius luridus), wisteria mealybug (Planococcus kraunhiae), two-striped rice bug (Stenotus binotatus), two-striped leafhopper (Arboridia apicalis), two-striped rice leafhopper (Macrosteles fascifrons), spotted stink bug (Dolycoris baccarum), spotted black rice bug (Adelphocoris triannulatus), grape aphid (Viteus vitifolii), ground cherry bug (Acanthocoris sordidus), narrow-legged stink bug (Leptocorisa acuta), narrow-winged long-legged bug (Macropes obnubilus), narrow-legged stink bug (Cletus punctiger), narrow-legged stink bug (Riptortus clavatus), potato piscid (Paratrioza cockerelli), Japanese butterbur moth (Aphrophora costalis), Japanese spotted grass bug (Lygus disponsi), spotted rice bug (Lygus saundersi), pine mealybug (Crisicoccus pini), pine leafhopper (Empoasca abietis), Matsumoto mealybug (Crisicoccus matsumotoi), bean aphid (Aphis craccivora), the spotted stink bug (Megacopta punctatissimum), the spotted stink bug (Eysarcoris guttiger), the citrus persimmon scale (Lepidosaphes beckii), the citrus psyllid (Diaphorina citri), the citrus black aphid (Toxoptera citricidus), the citrus mealybug (Planococcuscitri), citrus whitefly (Dialeurodes citri), citrus spine whitefly (Aleurocanthus spiniferus), citrus mealybug (Pseudococcus citriculus), citrus leafhopper (Zyginella citri), citrus cotton scale (Pulvinaria citricola), citrus placode scale (Coccus discrepans), citrus round scale (Pseudaonidia duplex), citrus cotton scale (Pulvinaria aurantii), dogwood scale (Lecanium corni), southern green stink bug (Nezara viridula), wheat leaf bug (Stenodema calcaratum), wheat neck aphid (Rhopalosiphum padi), wheat long-horn aphid (Sitobion akebiae), wheat green aphid (Schizaphis graminum), wheat leafhopper (Sorhoanus tritici), straw corn aphid (Brachycaudus helichrysi), purple stink bug (Carpocoris purpureipennis), peach aphid (Myzus persicae), peach butterbur aphid (Hyalopterus pruni), willow aphid (Aphis farinose yanagicola), willow earworm (Metasalis populi), Yanon scale (Unaspis yanonensis), mountain psylla (Mesohomotoma camphorae), snow willow aphid (Aphis spiraecola), apple aphid (Aphis pomi), apple persimmon scale (Lepidosaphes ulmi), Apple psylla (Psylla mali), Black apple leafhopper (Heterocordylus flavipes), Apple horn aphid (Myzus malisuctus), Apple leafhopper (Aphidonuguis mali), Apple leafhopper (Orientus ishidai), Apple fly aphid (Ovatusmalicolens), apple aphid (Eriosoma lanigerum), ruby ​​wax moth (Ceroplastes rubens), and cotton aphid (Aphis gossypii).

[0112] Examples of pests that belong to the order Coleoptera include the Japanese longhorn beetle (Xystrocera globosa), the green leaf beetle (Paederus fuscipes), the green leaf beetle (Eucetonia roelofsi), the azuki bean weevil (Callosobruchus chinensis), the sweet potato weevil (Cylas formicarius), the alfalfa weevil (Hypera postica), the rice weevil (Echinocnemus squameus), the rice leaf beetle (Oulema oryzae), the rice root beetle (Donacia provosti), the rice water weevil (Lissorhoptrus oryzophilus), the potato leaf beetle (Colasposoma dauricum), the potato weevil (Euscepes postfasciatus), and the common ladybird beetle (Epilachna varivestis), kidney bean weevil (Acanthoscelides obtectus), western corn rootworm (Diabrotica virgifera virgifera), plum vest weevil (Involvulus cupreus), cucumber leaf beetle (Aulacophora femoralis), pea weevil (Bruchus pisorum), large 24-spotted ladybird beetle (Epilachna vigintioctomaculata), oak leaf beetle (Carpophilus dimidiatus), tortoise leaf beetle (Cassida nebulosa), yellow-legged flea beetle (Luperomorpha tunebrosa), striped flea beetle (Phyllotreta striolata), yellow-spotted longhorn beetle (Psacothea hilaris), yellow-spotted longhorn beetle (Aeolesthes chrysothrix), chestnut weevil (Curculio sikkimensis), chestnut beetle (Carpophilus hemipterus), flower beetle (Oxycetonia jucunda), corn rootworms (Diabrotica spp.), scarab beetle (Mimela splendens), rice weevil (Sitophilus zeamais), red flour beetle (Tribolium castaneum), rice weevil (Sitophilus oryzae), lesser red flour beetle (Palorus subdepressus), cockchafer beetle (Melolontha japonica), spotted longhorn beetle (Anoplophora malasiaca), mealworm beetle (Neatus picipes), Colorado potato beetle (Leptinotarsa ​​decemlineata), southern corn rootworm (Diabrotica undecimpunctata howardi), grass weevil (Sphenophorus venatus), four-spotted long-necked beetle (Crioceris quatuordecimpunctata), plum curculion (Conotrachelus nenuphar, radish weevil (Ceuthorhynchidius albosuturalis), radish leaf beetle (Phaedon brassicae), cigarette beetle (Lasioderma serricorne), small weevil (Sitona japonicus), brown dung beetle (Adoretus tenuimaculatus), brown mealworm beetle (Tenebrio molitor), brown dung beetle (Basilepta balyi), nail weevil (Hypera nigrirostris), tentacle leaf beetle (Chaetocnema concinna), cuprea beetle (Anomala cuprea), long-legged scarab beetle (Heptophylla picea), 24-spotted ladybird beetle (Epilachna vigintioctopunctata), northern corn rootworm (Diabrotica longicornis), flower beetles (Eucetonia pilifera), wireworms (Agriotes spp.), lesser cutworm beetle (Attagenus unicolor japonicus), lesser yellow-winged monkey beetle (Pagria signata), lesser Japanese scarab beetle (Anomala rufocuprea), lesser red flour beetle (Palorus ratzeburgii), lesser mealworm beetle (Alphitobius laevigatus), lesser round cutworm beetle (Anthrenus verbasci), flat-headed wood borer (Lyctus brunneus), flat-headed red flour beetle (Tribolium confusum), lesser two-striped leaf beetle (Medythia nigrobilineata), grape tiger longhorn beetle (Xylotrechus pyrrhoderus), potato leaf beetle (Epitrix cucumeris), pine bark beetle (Tomicus piniperda), Japanese pine longhorn beetle (Monochamus alternatus), Japanese beetle (Popillia japonica), bean tiger beetle (Epicauta gorhami), maize weevil (Sitophilus zeamais), peach vest weevil (Rhynchites heros), vegetable weevil (Listroderes costirostris), cowpea weevil (Callosobruchus maculatus), apple weevil (Phyllobius armatus), apple blossom weevil (Anthonomus pomorum), blue leaf beetle (Linaeidea aenea), and boll weevil (Anthonomus grandis).

[0113] Diptera (flies) pests include, for example, Culex pipiens pallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae, Hydrellia sasakii, Agromyza oryzae, Hydrellia griseola, Ophiomyia phaseoli, Dacus cucurbitae, and Drosophila suzukii. suzukii), Rhacochlaena japonica, Muscina stabulans, Megaselia spiracularis and other phorid flies, Clogmia albipunctata, Tipula aino, Phormia regina, Culex tritaeniorhynchus, Anopheles sinensis, Hylemya brassicae, and Asphondylia sp.), Seed fly (Delia platura), Onion fly (Delia antiqua), European cherry fruit fly (Rhagoletis cerasi), Culex pipiens molestus Forskal, Mediterranean fruit fly (Ceratitis capitata), Sciarid fungus gnat (Bradysia agrestis), Sugar beet root fly (Pegomya cunicularia), Tomato leafminer (Liriomyza sativae), Eggplant leafminer (Liriomyza bryoniae), Rootminer (Chromatomyia horticola), Onion leafminer (Liriomyza chinensis), Southern house mosquito (Culex quinquefasciatus), Aedes aegypti, Aedes albopictus, Bean leafminer (Liriomyza trifolii, tomato leafminer (Liriomyza sativae), oriental fruit fly (Dacus dorsalis), citrus fly (Dacus tsuneonis), wheat gall midge (Sitodiplosis mosellana), wheat stem miner (Meromuza nigriventris), Mexican fruit fly (Anastrepha ludens), and apple fly (Rhagoletis pomonella).

[0114] Examples of Hymenoptera (Hymenoptera) pests include Pristomyrmex pungens, ant wasps, Monomorium pharaohnis, Pheidole noda, Athalia rosae, chestnut gall wasp (Dryocosmus kuriphilus), black mountain ant (Formica fusca japonica), hornets (Vespinae, Wasp), Athalia infumata infumata, Arge pagana, Athalia japonica, leafcutter ants (Acromyrmex spp.), fire ants (Solenopsis spp.), apple sawflies (Arge mali), and orange ants (Ochetellus glaber).

[0115] Examples of Orthoptera (Orthoptera) pests include the Japanese grasshopper (Homorocoryphus lineosus), the mole cricket (Gryllotalpa sp.), the Japanese carp locust (Oxya hyla intricata), the rice grasshopper (Oxya yezoensis), the Japanese migratoria locust (Locusta migratoria), the long-winged grasshopper (Oxya japonica), the Japanese grasshopper (Homorocoryphus jezoensis), and the field cricket (Teleogryllus emma).

[0116] Examples of Thripida pests include red banded thrips (Selenothrips rubrocinctus), rice thrips (Stenchaetothrips biformis), rice thrips (Haplothrips aculeatus), rice thrips (Ponticulothrips diospyrosi), yellow flower thrips (Thrips flavus), flower thrips (Anaphothrips obscurus), cusk thrips (Liothrips floridensis), gladiolus thrips (Thrips simplex), black-spotted flower thrips (Thrips nigropilosus), croton thrips (Heliothrips haemorrhoidalis), and mulberry thrips (Pseudodendrothrips mori), Cosmos thrips (Microcephalothrips abdominalis), Brown weasel thrips (Leeuwenia pasanii), Brown weasel thrips (Litotetothrips pasaniae), Citrus thrips (Scirtothrips citri), Chinese weasel thrips (Haplothrips chinensis), Soybean thrips (Mycterothrips glycines), Soybean light brown thrips (Thrips setosus), Tea leaf thrips (Scirtothrips dorsalis), Tea black thrips (Dendrothrips minowai), Japanese claw thrips (Haplothrips niger), Onion thrips (Thrips tabaci), Black onion thrips (Thrips alliorum), flower thrips (Thrips hawaiiensis), flower thrips (Haplothrips kurdjumovi), hair thrips (Chirothrips manicatus), plain flower thrips (Frankliniella intonsa), loquat flower thrips (Thrips coloratus), western flower thrips (Franklinella occidentalis), southern flower thrips (Thripspalmi), Frankliniella lilivora, and Liothrips vaneeckei.

[0117] Examples of pests of the order Acarina include Tetranychus truncatus, Tetranychus viennensis, Tetranychus kanzawai, Acaphylla theavagrans, Polyphagotarsonemus latus, Aculops lycopersici, Tetranychus urticae, Eriophyes chibaensis, Brevipalpus sp., Tyrophagus similis, Panonychus citri, Brevipalpus phoenicis, and Phyllocoptruta citri), apple rust mite (Aculus schlechtendali), apple red mite (Panonychus ulmi), robin bulb mite (Rhyzoglyphus robini), bulb mite (Sancassania sp.), and the like.

[0118] Examples of termite pests include the Amami termite (Reticulitermes miyatakei), the American dry wood termite (Incisitermes minor), the Formosan termite (Coptotermes formosanus), the Japanese termite (Hodotermopsis japonica), the Formosan termite (Reticulitermes sp.), the Japanese yellow termite (Reticulitermes flaviceps amamianus), the Japanese staghorn termite (Glyptotermes kushimensis), the Formosan termite (Coptotermes guangzhoensis), the Japanese yellow termite (Neotermes koshunensis), the Japanese staghorn termite (Glyptotermes kodamai), the Satsuma termite (Glyptotermes satsumensis), the Japanese giant termite (Cryptotermes domesticus), and the Taiwan termite (Odontotermes formosanus), Glyptotermes nakajimai, Pericapritermes nitobei, and Reticulitermes speratus.

[0119] Examples of cockroach pests include the Smoky brown cockroach (Periplaneta fuliginosa), the German cockroach (Blattella germanica), the Asian cockroach (Blatta orientalis), the Brown cockroach (Periplaneta brunnea), the lesser German cockroach (Blattella lituricollis), the Japanese cockroach (Periplaneta japonica), and the American cockroach (Periplaneta americana).

[0120] Examples of nematodes include the strawberry root nematode (Nothotylenchus acris), the rice root nematode (Aphelenchoides besseyi), the northern root-knot nematode (Pratylenchus penetrans), the northern root-knot nematode (Meloidogyne hapla), the sweet potato root-knot nematode (Meloidogyne incognita), the potato cyst nematode (Globodera rostochiensis), the Java root-knot nematode (Meloidogyne javanica), the soybean cyst nematode (Heterodera glycines), the southern root-leakage nematode (Pratylenchus coffeae), the wheat root-leakage nematode (Pratylenchus neglectus), and the citrus root nematode (Tylenchus semipenetrans).

[0121] Examples of mollusks include apple snails (Pomacea canaliculata), African snails (Achatina fulica), slugs (Meghimatium bilineatum), brown slugs (Lehmannina valentiana), red slugs (Limax flavus), and the light blue snail (Acusta despecta sieboldiana).

[0122] The agricultural and horticultural fungicide of the present invention also has a strong insecticidal effect against another pest, the tomato osmosis moth (Tuta absoluta).

[0123] The agricultural and horticultural fungicides of the present invention, which contain the amide compound represented by the general formula [I] or a salt thereof as an active ingredient, have a remarkable control effect against the above-mentioned diseases that damage paddy field crops, field crops, fruit trees, vegetables, other crops, flowers, etc., and therefore the expected effects of the agricultural and horticultural fungicides of the present invention can be achieved by treating them with the compound in a nursery facility, paddy field, field, seeds of fruit trees, vegetables, other crops, flowers, etc., paddy water, stems and leaves, or soil, etc., in accordance with the time when the disease is predicted to occur, before the disease occurs or at the time when the disease occurrence is confirmed. Application utilizing so-called systemic movement, in which the compound of the present invention is absorbed through the roots with or without passing through the soil, can also be carried out by treating the compound with the seedling soil of crops, flowers, etc., soil in a planting hole at the time of transplanting, the base of the plant, irrigation water, cultivation water in hydroponic cultivation, etc.

[0124] Useful plants for which the agricultural and horticultural fungicide of the present invention can be used include, but are not limited to, 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), bell peppers, eggplant, strawberries, peppers, okra, chives, etc.), root vegetables (carrots, potatoes, sweet potatoes, taro, daikon radish, turnips, lotus root, burdock, garlic, onions, etc.), and the like. Examples of plants that can be used include: crops for processing (cotton, hemp, beets, hops, sugarcane, sugar beets, olives, rubber, coffee, tobacco, tea, etc.), melons (pumpkin, cucumber, watermelon, Sakhalin gourd, melon, etc.), pasture grasses (orchard grass, sorghum, timothy, clover, alfalfa, etc.), turfgrass (Korean grass, bentgrass, etc.), ornamental crops for perfumes and the like (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemum, rose, carnation, orchid, tulip, lily, etc.), garden trees (ginkgo, cherry trees, Japanese maple, etc.), and forest trees (abies firs, spruces, pines, hiba, cedar, cypress, eucalyptus, etc.).

[0125] The above-mentioned "plant" also includes plants to which tolerance 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.

[0126] Examples of "plants" that have been given tolerance through classical breeding methods include rapeseed, wheat, sunflower, and rice that are resistant to imidazolinone ALS-inhibiting herbicides such as imazethapyr, with rice already being sold under the trade name Clearfield (registered trademark). Similarly, soybeans that have been given tolerance to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron methyl through classical breeding methods are already being sold under the trade name STS soybeans. Similarly, examples of plants that have been given tolerance to acetyl-CoA carboxylase inhibitors such as trione oxime and aryloxyphenoxypropionic acid herbicides through classical breeding methods include SR corn. 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 elsewhere. Furthermore, mutant acetyl-CoA carboxylases resistant to acetyl-CoA carboxylase inhibitors have been reported in Weed Science, Vol. 53, pp. 728-746 (2005), and plants resistant to acetyl-CoA carboxylase inhibitors can be produced by introducing such mutant acetyl-CoA carboxylase genes into plants by genetic engineering techniques or by introducing a mutation related to conferring resistance into plant acetyl-CoA carboxylase. Furthermore, chimeraplasty techniques (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: By introducing a nucleic acid with a base substitution mutation, such as those represented by the following (see, for example, the references 316-318), into plant cells to introduce site-specific amino acid substitution mutations into the plant's acetyl-CoA carboxylase gene, ALS gene, or the like, it is possible to produce plants that are resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, or the like, and the agricultural and horticultural fungicide of the present invention can also be used on these plants.

[0127] Further examples of toxins expressed in genetically modified plants include insecticidal proteins derived from Bacillus cereus and Bacillus popiliae; δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, and Cry9C derived from Bacillus thuringiensis, insecticidal proteins such as VIP1, VIP2, VIP3, and VIP3A; insecticidal proteins derived from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, wasp toxins, and insect-specific neurotoxins; fungal toxins; plant lectins; agglutinins; trypsin inhibitors, serine protease inhibitors, patatin, cystadens, and the like. ribosome-inactivating proteins (RIPs) such as ricin, corn-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; and glucanase.

[0128] Toxins expressed in such genetically modified plants also include hybrid toxins, truncated toxins, and modified toxins of δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, or Cry35Ab, and insecticidal proteins such as VIP1, VIP2, VIP3, or VIP3A. Hybrid toxins are produced using recombinant technology by combining different domains of these proteins in new ways. A known example of a truncated toxin is Cry1Ab, which lacks a portion of its amino acid sequence. Modified toxins have one or more amino acids substituted in the native toxin. 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.

[0129] The toxins contained in these recombinant plants confer resistance to Coleoptera, Hemiptera, Diptera, Lepidoptera, and nematodes, among others. The agricultural and horticultural fungicide of the present invention can be used in combination with or as a systemic combination with these technologies.

[0130] To control various diseases, the agricultural and horticultural fungicide of the present invention may be applied directly or in the form of an appropriate dilution or suspension in an amount effective for disease control to plants where the disease is expected to occur. For example, for diseases that occur in fruit trees, grains, vegetables, etc., it can be sprayed on the stems and leaves, or it can be used by soaking seeds in the fungicide, seed dressing, seed treatment such as calper treatment, incorporation into the entire soil layer, row application, incorporation into bed soil, treatment with cell seedlings, treatment in planting holes, treatment at the base of plants, top dressing, treatment in rice boxes, application on the surface of water, or by application to the soil etc. and absorption by the roots. In addition, it can be applied to nutrient solutions in nutrient solution (hydroponic) cultivation, by fumigation, trunk injection, etc. Furthermore, the agricultural and horticultural fungicide of the present invention may be used in an amount effective for controlling plant diseases 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, and may be used, for example, as a spray against stored grain pests, house pests, sanitary pests, forest pests, etc., or as a coating on building materials for houses, for smoking, as bait, etc. Furthermore, the agricultural and horticultural fungicide of the present invention may be used in an amount effective for controlling disease 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.

[0131] Seed treatment methods include, for example, a method in which seeds are soaked in a liquid or solid formulation, 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 coated onto the seed surface, a method in which the formulation is mixed with an adhesive carrier such as a resin or polymer and then coated onto the seeds, a method in which the formulation is sprayed around the seeds at the same time as planting, etc. The "seeds" to be treated with this seed treatment refer to plant bodies in the early stages of cultivation used for plant propagation, and include, in addition to seeds, bulbs, tubers, seed potatoes, sprouts, bulbils, bulbs, or plant bodies for vegetative propagation for cutting cultivation. When carrying out the method of use of the present invention, the term "soil" or "cultivation carrier" for plants refers to a support for cultivating crops, particularly a support for growing roots. The material is not particularly limited, and any material that allows plants to grow thereon may be used, such as soil, a seedling mat, or water. Specific examples of the material include sand, pumice, vermiculite, diatomaceous earth, agar, a gel-like substance, a polymeric substance, rock wool, glass wool, wood chips, and bark.

[0132] Examples of methods for spraying on the stems and leaves of crops 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 dust formulation is sprayed, or fumigation, etc. Examples of methods for application to soil include a method in which a liquid formulation is applied, with or without dilution, to the base of plants or a seedling bed for raising seedlings, etc., a method in which a granule is sprayed to the base of plants or a seedling bed for raising seedlings, etc., a method in which a dust formulation, wettable powder, water dispersible granules, granules, etc. is sprayed and mixed with the entire soil before sowing or transplanting, a method in which a planting hole is made before sowing or planting plants, a method in which a dust formulation, wettable powder, water dispersible granules, granules, etc. is sprayed on rows, etc., etc.

[0133] For application to rice seedling boxes, the formulation may vary depending on the application time, such as application at the time of sowing, application during the greening period, or application at the time of transplanting. The formulation may be a dust, water dispersible granule, or granule. Application can also be by mixing with the soil, such as mixing the soil with a dust, water dispersible granule, or granule, for example, by mixing with the bed soil, covering the soil, or by mixing with the entire soil. The soil and various formulations may simply be layered alternately and applied. For application to paddy fields, solid formulations such as jumbo formulations, pack formulations, granules, and water dispersible granules, or liquid formulations such as flowables and emulsifiable concentrates, are typically sprayed on flooded paddy fields. At the time of rice planting, an appropriate formulation can be sprayed or injected directly into the soil, or mixed with fertilizer. Furthermore, by using chemical solutions such as emulsions and flowables at the water inlet or irrigation equipment or other water inflow points into rice paddies, they can be applied in a labor-saving manner along with the water supply.

[0134] In field crops, the fungicide can be applied to seeds or to cultivation carriers adjacent to the plants during the sowing to seedling raising period. For plants sown directly in fields, direct application to seeds is preferred, as well as application to the base of plants during cultivation. Spraying treatment using granules or irrigation treatment in liquid form with the agent diluted or undiluted in water is possible. Mixing the granules with the cultivation carrier before sowing and then sowing is also a preferred treatment. For treatment of cultivated plants to be transplanted during the sowing and seedling raising period, direct application to seeds is preferred, as well as irrigation treatment of a liquid agent or spraying treatment of granules on the seedling bed. Furthermore, application of the granules to the planting hole at the time of planting or mixing with the cultivation carrier near the transplanting site is also preferred. The agricultural and horticultural fungicide of the present invention is generally formulated into a convenient form for use according to conventional methods for pesticide formulation. That is, the amide compound represented by the general formula [I] of the present invention or a salt thereof can be formulated into an appropriate dosage form, such as a suspension, emulsion, solution, wettable powder, water dispersible granule, granule, dust, tablet, pack, etc., by blending it in an appropriate ratio with an appropriate carrier, or if necessary, an adjuvant, and dissolving, separating, suspending, mixing, impregnating, adsorbing, or adhering it.

[0135] The agricultural and horticultural fungicide composition of the present invention may contain, in addition to the active ingredient, additives commonly used in pesticide formulations, as needed. Examples of such additives include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreading agents, adhesives, antifreeze agents, anticaking agents, disintegrants, and antidegradants. If necessary, preservatives, plant fragments, and the like may also be used as additives. These additives may be used alone or in combination of two or more.

[0136] 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 highly dispersed 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, and fumed silica (fumed silica, white carbon). These may be used alone or in combination of two or more.

[0137] 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; chain or cyclic ethers such as ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, and tetrahydrofuran; normal paraffin; naphthenic acid; Examples of suitable solvents include aliphatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, and alkylnaphthalenes, 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, N-alkylpyrrolidinone, and N-methylpyrrolidone, 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.

[0138] 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 such as polyoxyethylene nonylphenyl ether, 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 alkylphenyl ether ...s, polyoxyethylene alkylphenyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene alkylphenyl nonionic surfactants such as oxyethylene ether type silicones, ester type silicones, fluorine-based surfactants, 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, resinates, polyoxyethylene alkyl ether phosphates, and polyoxyethylene alkyl phenyl ether phosphates; laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, and alkyltrimethylammonium chloride;Examples of such surfactants include cationic surfactants such as alkylamine salts, e.g., alkyldimethylbenzalkonium chloride, and amphoteric surfactants, e.g., amino acid-type or betaine-type surfactants. These surfactants may be used alone or in combination of two or more.

[0139] Examples of binders and tackifiers include carboxymethyl cellulose 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-formalin condensates, and synthetic resin emulsions.

[0140] Examples of thickeners include water-soluble polymers such as xanthan gum, guar gum, diutan gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds, and polysaccharides, and inorganic fine powders such as high-purity bentonite and fumed silica (white carbon).

[0141] 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.

[0142] Examples of antifreezing agents include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

[0143] 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.

[0144] Examples of anti-decomposition agents include desiccants 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.

[0145] Examples of preservatives include potassium sorbate, 1,2-benzothiazolin-3-one, etc. Furthermore, other adjuvants 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 can also be used as needed.

[0146] 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, emulsifiable concentrate or wettable powder, an amount of 0.01 to 50 parts by weight (0.01 to 50% by weight based on the total weight of the agricultural and horticultural fungicide) is appropriate.

[0147] The amount of the agricultural and horticultural fungicide of the present invention to be used will vary depending on various factors, such as the purpose, the state of the target disease, the growth state of the crop, the tendency of the disease to occur, weather, environmental conditions, formulation, 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.

[0148] The agricultural and horticultural fungicide of the present invention can be used in combination with other agricultural and horticultural insecticides, miticides, nematicides, fungicides, biological pesticides, etc., in order to expand the range of pests and diseases to be controlled and the optimum control period, or to reduce the amount of application.It can also be used in combination with herbicides, plant growth regulators, fertilizers, etc., depending on the application situation.

[0149] Other agricultural and horticultural insecticides, acaricides and nematicides used for such purposes include, for example, 3,5-xylyl methylcarbamate (XMC), Bacillus thuringienses (e.g., Bacillus thuringienses aizawai, Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses kurstaki, Bacillus thuringienses tenebrionis, Bacillus thuringienses aizawai, Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses kurstaki, Bacillus thuringienses tenebrionis, Bacillus thuringienses aizawai, Bacillus thuringienses israelensis, Bacillus thuringienses aizawai ... Crystal protein toxins produced by bacteria such as Bacillus tenebrionis, BPMC (N-methylcarbamate-2-(1-methylpropyl)phenyl), Bt toxin-based insecticides, chlorfenson (CPCBS), dichlorodiisopropyl ether (DCIP), 3-dichloropropene (1,3-Dichloropropene: D-D), DDT, NAC, O-4-dimethylsulfamoylphenyl O,O-diethyl phosphorothioate (DSP), O-ethyl-O-4-nitrophenyl phenylphosphonothioate (O-ethyl O-4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate (tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, acinonapyr, azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate,Abamectin, afidopyropen, avermectin-B, amidoflumet, amitraz, alanycarb, aldicarb, aldoxycarb, aldrin, alpha-endosulfan, alpha-cypermethrin, alpha-bromadiolon (alpha-bromadiolone), albendazole, allethrin, isazofos, isamidofos, isoamidofos, isoxathion, isocycloseram, isofenphos, isoflualanam, isoprocarb (MIPC), epsilon-metofluthrin -metofluthrin), epsilon-momfluorothrin, ivermectin, imicyafos, imidacloprid, imiprothrin, indoxacarb, esfenvalerate, ethiofencarb, ethion, ethiprole, etoxazole azole), etofenprox, ethoprophos, etrimfos, emamectin, emamectin-benzoate, endosulfan, empenthrin, oxazosulfyl, oxamyl, oxydemeton-methyl, oxydeprofos (ESP),Oxibendazole, oxfendazole, potassium oleate, sodium oleate, cadusafos, kappa-bifenthrin, capric ester, galquin / silvateam, cartap, carbaryl, carbosulfan, carbofuran, gamma-cyhalothrin, xylylcarb, quinalphos, kinoprene, chinomethionate, glycerol citric acid fatty acid ester, glycerol fatty acid ester, glycerol acetate fatty acid ester Acetic acid fatty acid ester), cloethocarb, clothianidin, clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyfos, chlordimeform, chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorfenapyr, chlorphenapyr, chlorfenson, chlorfenvinphos, chlorfluazuron, chlorbenzilate, chloroprallethrin, chlorobenzoate, dicofol, salithion,Cyanophos (CYAP), diafenthiuron, diamidaphos (diamidafos), cyantraniliprole, theta-cypermethrin, cyetpyrafen (cyetpyrafen), dienochlor (dienochlor), cyenopyrafen (cyenopyrafen), dioxabenzophos (dioxabenzofos), diofenolan (diofenolan), sigma-cypermethrin (sigma-cypermethrin), cyclaniliprole (cyclaniliprole), diclofenthion (dichlofenthion: ECP), cyclobutrifluram (cyclobutrifluram), cycloprothrin (cycloprothrin), dichlorvos (dichlorvos: DDVP), dichloromezotiaz, disulfoton, dinotefuran, cyhalodiamide, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron, cyflumetofen, diflovidadin, cyproflanilide, cyhexatin, cypermethrin, cybenzoxasulf cybenzoxasulfyl, dimpropyridaz, dimethylvinphos, dimethoate, dimefluthrin, silafluofen, cyromazine, spidoxamat, spinetoram, spinosad, spirodiclofen, spirotetramat, spiropidione, spirobudifen,Spiromesifen, sulfiflumin, sulfluramid, sulprofos, sulfoxaflor, sulfoxamyl, zeta-cypermethrin, sorbitan fatty acid esters ester), diazinon, tau-fluvalinate, dazomet, thiacloprid, thiapyrachlor, thiamethoxam, tioxazafen, thiodicarb, thiocyclam, thiosultap, thiosultap sodium, thionazin, thiometon, thiolanthraniliprole (tiorantraniliprole), cyclopyrazoflor (tyclopyrazoflor), DEET (deet), dieldrin (dieldrin), tetrachlorantraniliprole (tetrachlorantraniliprole), tetrachlorvinphos (tetrachlorvinphos), tetradifon (tetradifon), tetraniliprole (tetraniliprole), tetramethylfluthrin (tetramethylfluthrin), tetramethrin (tetramethrin), tebu Pirimphos (tebupirimfos), tebufenozide (tebufenozide), tebufenpyrad (tebufenpyrad), tefluthrin (tefluthrin), teflubenzuron (teflubenzuron), demeton-S-methyl (demeton-S-methyl), temephos (temephos), deltamethrin (deltamethrin), terbufos (terbufos), doramectin (doramectin), tralopyril (tralopyril), tralomethrin (tralomethrin),Transfluthrin, triazamate, triazuron, trioxyflanilide, trichlamide, trichlorphon (DEP), triflumuron, triflumezopyrim, tolfenpyrad, naled (BRP), nicofluprole, nithiazine, nitenpyram, novaluron, noviflumuron, hydroprene, vadescana (GreenLight) Biosciences), vaniliprole, vamidothion, parathion, parathion-methyl, halfenprox, halofenozide, pioxaniliprole, bistrifluron, bisultap, bisulfufen, hydramethylnon, hydroxypropyl starch, hydroxypropyl starch liquid solution), binapacryl (binapacryl), vinylfluthrin (vinylfluthrin), bifenazate (bifenazate), bifenthrin (bifenthrin), piflubumide (pyflubumide), piperfuranilide (piperflanilide), pymetrozine (pymetrozine), pyraclofos (pyraclorfos), pyrafluprole (pyrafluprole), pyridaphenthion (pyridafenthion), pyridaben (pyridaben), pyridalyl (pyridalyl), pyrifluquinazon (pyrifluquinazon),Pyriprole, pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methyl, pyrethrins, fipronil, fenazaquin, fenamiphos, phenisobromorate omolate), fenitrothion (fenitrothion:MEP), fenoxycarb, fenothiocarb, fenothrin, fenobucarb, fensulfothion, fenthion (fenthion:MPP), phenthoate (phenthoate:PAP), fenvalerate, fenpyroximate mate), fenpropathrin, fenbendazole, fosthiazate, formetanate, butathiofos, buprofezin, furazaindolizine, furathiocarb, prallethrin, fluacrypyrim , fluazinam (fluazinam), fluazuron (fluazuron), fluensulfone (fluensulfone), fluxametamide (fluxametamide), flucycloxuron (flucycloxuron), flucythrinate (flucythrinate), fluvalinate (fluvalinate), flupyradifurone (flupyradifurone), flupyrazofos (flupyrazofos), flupirimin (flupyrimin), flupiroxystrobin (flupyroxystrobin), flufiprole (flufiprole), flufenerim (flufenerim),Flufenoxystrobin, flufenoxuron, flufenzine, flufenprox, fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flupentiofenox, flumetnicam, flumethrin, flurimfen, prothiofos, protrifenbut, flonicamid, propaphos, propargite (BPPS), propylene glycol mono fatty acid ester ester), profenofos, broflanilide, profluthrin, propoxur (PHC), flometoquin, bromopropylate, beta-cyfluthrin, hexaflumuron, hexythiazox, heptafluthrin, heptenophos, permethrin, benclo Benclothiaz (benclothiaz), bendiocarb (bendiocarb), benzpyrimoxan (benzpyrimoxan), bensultap (bensultap), benzoximate (benzoximate), bentioflumin (bentioflumin), benfuracarb (benfuracarb), phoxim (phoxim), phosalone (phosalone), fosthiazate (fosthiazate), fosthietan (fosthietan), phosphamidon (phosphamidon), phosphocarb (phosphocarb), phosmet (phosmet: PMP),Polyoxyethylene sorbitan fatty acid ester, polyoxyethylene hexan fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene fatty acid ester, polyoxin complex (polioxins), polyglycerol fatty acid ester, polynactins, formetanate, formothion, phorate, machine oil oil), malathion, milbemycin, milbemycin A, milbemectin, mecarbam, mesulfenphos, methomyl, metaldehyde, metaflumizone, methamidophos, metam-ammonium, metam-sodium, methiocarb, methidathion (DMTP), methylisothiocyanate iocyanate), methyl neodecanamide (methylneodecanamide), methyl parathion (methylparathion), metoxadiazone (metoxadiazone), methoxychlor (methoxychlor), methoxyfenozide (methoxyfenozide), metofluthrin (metofluthrin), methoprene (methoprene), metolcarb (metolcarb), mevinphos (mevinphos), meperfluthrin (meperfluthrin), monocrotophos (monocrotophos), monosultap (monosultap), momfluorothrin (momfluorothrin), lauric acid ester (lauric ester),Lambda-cyhalothrin, ryanodine, lufenuron, lecithin, rescalure, resmethrin, lepimectin, rotenone, levamisol hydrochloride, reduced starch saccharide, ledprona, fenbutatin oxide, fatty acid glycerides, morantel tartarate, methyl bromide, tricyclohexyltin hydroxide (cyhexatin), calcium cyanamide, calcium polysulfide, compounded oil (saf oil), and machine oil, which is a physical control agent. Examples include nicotine oil, sulfur, and nicotine sulfate.

[0150] Agricultural and horticultural fungicides used for similar purposes include, for example, aureofungin, azaconazole, azithiram, acipetax, acibenzolar, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, aminotipyr, ampropylfos, ametoctradin, and allyl alcohol. alcohol), aldimorph, amobam, isotianil, isovaledione, isopyrazam, isofetamide, isofetamide, isoflucipram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin, iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine ), iminoctadine albesilate (iminoctadine-albesilate), iminoctadine acetate (iminoctadine-triacetate), imibenconazole (imibenconazole), uniconazole (uniconazole), uniconazole P (uniconazole-P), echlomezole (echlomezole), edifenphos (edifenphos), etaconazole (etaconazole), ethaboxam (ethaboxam), ethirimol (ethirimol), etem (etem), ethoxyquin (ethoxyquin), etridiazole (etridiazole), enestroburin (enestroburin), enoxastrobin (enoxastrobin),Epoxiconazole, oxadixyl, oxycarboxin, oxathiapiprolin, 8-oxyquinoline copper (copper-8-quinolinolate), oxytetracycline, oxine copper (copper-oxinate), oxpoconazole, oxpoconazole-fumarate, oxolinic acid, octhilinone, ofurace, orysastrobin, carbam, metam-sodium), kasugamycin (kasugamycin), Galquin (Galquin / Silvateam), carbamorph (carbamorph), carpropamid (carpropamid), carbendazim (carbendazim), carboxin (carboxin), carvone (carvone), quinazamid (quinazamid), quinacetol (quinacetol), quinaminoprole (quinaminoprole), quinoxyfen (quinoxyfen), quinofumelin (quinofumelin), quinomethionate (quinomethionate), captafol (captafol), captan (captan), chiralaxyl (kiralaxyl), Quinconazole (quinconazole), quintozene (quintozene), guazatine (guazatine), cufraneb (cufraneb), cuprobam (cuprobam), coumoxystrobin (coumoxystrobin), gliodin (glyodin), griseofulvin (griseofulvin), climbazole (climbazole), cresol (cresol), kresoxim-methyl (kresoxim-methyl), chlozolinate (chlozolinate), clotrimazole (clotrimazole), chlobenthiazone (chlobenthiazone), chloraniformethan (chloraniformethan), chloranil (chloranil),Chlorquinox, chloropicrin, chlorphenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, chloroneb, zalilamid, salicylanilide, cyazofamid, diethyl pyrocarbonate pyrocarbonate), diethofencarb, cyclafuramid, diclocymet, dichlozoline, diclobutrazol, dichlofluanid, cycloheximide, dichlobentiazox, diclomezine, dicloran, dichlorophen, dichlorone, disulfiram, ditalimfos, dithianon, diniconazole, diniconazole M onazole-M), zineb (zineb), dinocap (dinocap), dinocton (dinocton), dinosulfon (dinosulfon), dinoterbone (dinoterbon), dinobuton (dinobuton), dinopenton (dinopenton), dipymetitrone (dipyrithione), diphenylamine (diphenylamine), difenoconazole (difenoconazole), cyflufenamid (cyflufenamid), diflumetorim (diflumetorim), cyproconazole (cyproconazole), cyprodinil (cyprodinil), cyprofuram (cyprofuram), cypendazole (cypendazole), simeconazole (simeconazole),Dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, methyl bromide, ziram, silthiofam, streptomycin, spiroxamine, sultropen, sedaxane, seboctylamine, zoxamide, dazomet, thiadiazine, tiadinil, thiadifluor, thiabendazole, tioximid, thiochlorfenfim orfenphim, thiophanate, thiophanate-methyl, thicyofen, thioquinox, chinomethionat, thifluzamide, thiram, decafentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid acid), tebuconazole (tebuconazole), tebufloquin (tebufloquin), dodicin (dodicin), dodine (dodine), dodecylbenzenesulfonic acid bisethylenediamine copper complex salt (II) (DBEDC), dodemorph (dodemorph), drazoxolone (drazoxolon), triadimenol (triadimenol), triadimefon (triadimefon), triazbutil (triazbutil), triazoxide (triazoxide), triamiphos (triamiphos), triarimol (triarimol), trichlamide (trichlamide), triclopyricarb (triclopyricarb),Tricyclazole, triticonazole, tridemorph, tributyltin oxide, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolprocarb, natamycin, nabam, nitrothal-isopropyl, nitrostyrene, nuarimol, copper nonylphenol sulfonate, halacrinate, validamycin, valifenalate, harpin protein protein), picarbutrazox, bixafen, picoxystrobin, picobenzamide, pydiflumetofen, bithionol, bitertanol, hydroxyisoxazole, hydroxyisoxazole potassium, binapacryl, bifeni Biphenyl, piperaline, hymexazol, pyraoxystrobin, pyracarbolid, pyraclostrobin, pyrazophos, pyrametostrobin, pyriophenone, pyridinitril, pyrisoxazole, pyridaclomethyl,Pyrifenox, pyribencarb, pyriminostrobin, pyrimethanil, pyroxychlor, pyroxyfur, pyroquilon, vinclozolin, ferbam, famoxadone, fenapanil, fenamidone, and fenaminosulf enaminosulf), phenaminestrobin (fenaminstrobin), fenarimol (fenarimol), fenitropan (fenitropan), pheneptamidoquin (feneptamidoquin), fenoxanil (fenoxanil), fenopyramid (fenopyramid), ferimzone (ferimzone), ferbam (ferbam), fentin (fenpiclonil), fenpicoxamid (fenpicoxamid), fenpyrazamine ( fenpyrazamine), fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid, phthalide, buthiobate, butylamine, bupirimate, fuberidazole, blasticidin-S, furam Topil (furametpyr), furalaxyl (furalaxyl), fluacrypyrim (fluacrypyrim), fluazinam (fluazinam), fluindapyr (fluindapyr), fluoxastrobin (fluoxastrobin), fluoxapiprolin (fluoxapiprolin), fluoxytioconazole (fluoxytioconazole), fluotrimazole (fluotrimazole), fluopicolide (fluopicolide), fluopimomide (fluopimomide),Fluopyram, fluoroimide, furcarbanil, fluxapyroxad, fluquinometoate, fluquinconazole, fluconazole, fluconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, flufenoxadiazam, flufenoxystrobin, furfural, flubeneteram, flumecyclox, flumethylsulfonim, flumetover, flumo Flumorph, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole, propamocarb, pronitridine, propiconazole, propineb, furophanate, probenazole ), bromuconazole (bromuconazole), florylpicoxamid (florylpicoxamid), hexachlorobutadiene (hexachlorobutadiene), hexaconazole (hexaconazole), hexylthiofos (hexylthiofos), bethoxazin (bethoxazin), benalaxyl (benalaxyl), benalaxyl-M (benalaxyl-M), benodanil (benodanil), benomyl (benomyl), pefurazoate (pefurazoate), benquinox (benquinox),Penconazole, benzamorph, pencycuron, benzohydroxamic acid, benzovindiflupyr, bentaluron, benthiazole, benthiavalicarb, benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, phosdiphen, fosetyl, fosetyl aluminum, polyoxins, polyoxolin, polycarbamate, folpet, formaldehyde, machine oil oil), maneb, mancozeb, mandipropamid, mandestrobin, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid, methasulfocarb, metazoxolone, metam, metam-sodium, metalaxyl, metalaxyl-M, metarylpicoxamid, metiram, methyl isothiocyanate isothiocyanate), methyltetraprole, mepthyldinocap, metconazole, metsulfovax, metofuroxam, metominostrobin,Inorganic disinfectants such as metrafenone (metrafenone), mepanipyrim (mepanipyrim), mefenoxam (mefenoxam), mefentrifluconazole (mefentrifluconazole), meptyldinocap (meptyldinocap), mepronil (mepronil), mebenil (mebenil), methyl iodide (iodomethane), rabenzazole (rabenzazole), benzalkonium chloride (benzalkonium chloride), basic copper chloride (basic copper chloride), basic copper sulfate (basic copper sulfate), metallic silver (silver), sodium hypochlorite (sodium hypochlorous acid), cupric hydroxide (cupric hydroxide), wettable sulfur (wettable sulfur), lime sulfur mixture (calcium polysulfide), potassium hydrogen carbonate (potassium hydrogen carbonate), sodium hydrogen carbonate (sodium hydrogen carbonate), inorganic sulfur (sulfur), anhydrous copper sulfate (copper sulfate anhydride), dimethyldithiocarbamic acid nickel (nickel Examples include copper compounds such as dimethyldithiocarbamate, 8-hydroxyquinoline copper (oxine copper), zinc sulfate, and copper sulfate pentahydrate.

[0151] Similarly, herbicides such as 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 din), 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 lfuron), icafolin, isouron, isocarbamide, isoxachlortole, isoxapyrifop, isoxafenacil, isoxaflutole, isoxaben, isocil, isonoruron, isoproturon, isopropalin, isopolinate, isomethiozin,Inabenfide, ipazine, iptriazopyrid, ipfencarbazone, iprimidam, imazaquin, imazapic, imazapyr, imazamethapyr, imazamethabenz, imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolebutyric acid, indolauxipyr, indolauxipyr-cyanomethyl (indolauxipyr-cyanomethyl), uniconazole-P (uniconazole-P), eglinazine (eglinazine), esprocarb (esprocarb), ethametsulfuron (ethametsulfuron), ethametsulfuron-methyl (ethametsulfuron-methyl), ethalfluralin (ethalfluralin), ethiolate (ethiolate), ethychlozate-ethyl (ethychlozate-ethyl), ethidimuron (ethidimuron), etinofen (etinofen), ethephon (ethephon), ethoxysulfuron (eth oxysulfuron), ethoxyfen (ethoxyfen), etnipromid (etnipromid), etofumesate (ethofumesate), etobenzanid (etobenzanid), epirifenacil (epyrifenacil), epronaz (epronaz), erbon (erbon), endothal (endothal), oxadiazon (oxadiazon), oxadiargyl (oxadiargyl), oxaziclomefone (oxaziclomefone), oxasulfuron (oxasulfuron), oxapyrazon (oxapyrazon), oxyfluorfen (oxyfluorfen),Oryzalin, orthosulfamuron, orbencarb, cafenstrole, cambendichlor, carbasulam, carfentrazone, carfentrazone-ethyl, karbutilate, carbetamide, carboxazole azole), quizalofop, quizalofop-P, quizalofop-ethyl, xylachlor, quinoclamine, quinonamid, quinclorac, quinmerac, cumyluron, clacyfos, cliodinate, glyphosate, glyphosate, Glufosinate (glufosinate), glufosinate-P (glufosinate-P), credazine (credazine), clethodim (clethodim), cloxyfonac (cloxyfonac), clodinafop (clodinafop), clodinafop-propargyl (clodinafop-propargyl), clotoluron (chlorotoluron), clopyralid (clopyralid), cloproxydim (cloproxydim), cloprop (cloprop), clobromuron (chlorbromuron), clofop (clofop), clomazone (clomazone), chlomethoxynil (chlomethoxynil), chlomethoxyfen (chlomethoxyfen), clomeprop (clomeprop), chlorazifop (chlorazifop), chlorazine (chlorazine), chloranocryl (chloranocryl), chloramben (chloramben), cloransulam (cloransulam), cloransulam-methyl (cloransulam-methyl),Chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron, chlorthal, chlorthiamid, chlortoluron, chlornitrofen, chlorfenac, chlorfenprop, chlorphthalim, chlorbufam, chlorflurazole, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chloreturon, chloroxynil, chloroxuron, chlorotoluron, chloropon, cypirafluon (cypyrafluone), saflufenacil, cyanazine, cyanatrin, di-allate, diuron, diethamquat, dioxopyritrione, dicamba, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron cyclosulfamuron), cyclopyranil, cyclopyrimorate, dicloprop, dicloprop-P, dichlobenil, dichlobenz-methyl, diclofop, diclofop-methyl, dichromate, dichlormate, dichloralurea,Diquat, cisanilide, disul, siduron, dithiopyr, dinitramine, cinidon-ethyl, dinosam, cinosulfuron, dinoseb, dinoterb, dinofenate, dinoprop, cyhalofop-butyl, di Fenamide (diphenamid), difenoxuron (difenopenten), difenzoquat (difenzoquat), sibutryne (cybutryne), cyprazine (cyprazine), cyprazole (cyprazole), diflufenican (diflufenican), diflufenzopyr (diflufenzopyr), dipropetryn (dipropetryn), cypromid (cyperquat), gibberellin (gi bberellin), simazine, dimexano, dimesulfazet, dimethachlor, dimedazon, dimethametryn, dimethenamid, simetryn, simeton, dimepiperate, dimepyrolimet, dimefuron, cinflubrorin (cinflubrolin), cinmethylin (cinmethylin), swep (swep), sulglycapin (sulglycapin), sulcotrione (sulcotrione), sulfalate (sulfallate), sulfentrazone (sulfentrazone), sulfosulfuron (sulfosulfuron), sulfometuron (sulfometuron), sulfometuron-methyl (sulfometuron-methyl), secbumeton (secbumeton), sethoxydim (sethoxydim),Sebuthylazine, terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyr, thiafenacil, thiencarbazone, thiencarbazone-methyl, thiocarbazil, thioclorim, thiobencarb (thiobencarb), thidiazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmetryn, tetflupyrolimet, tetrafluron, thenylchlor, tebutam, tebuthiuron uthiuron, terbumeton, tepraloxydim, tefuryltrione, tembotrione, delachlor, terbacil, terbucarb, terbuchlor, terbuthylazine, terbutryn, topramezone, tralkoxydim im), triaziflam, triasulfuron, triafamone, triallate, trietazine, tricamba, triclopyr, tridiphane, tritac, tritosulfuron, tripyrasulfone, trifludimoxazin,Triflusulfuron, triflusulfuron-methyl, trifluralin, trifloxysulfuron, tripropindan, tribenuron-methyl, tribenuron, triphop, trifopsime, trimeturon, tolpyralate, naptalam, naproanilide, naproanilide, napropamide, nicosulfuron, nitralin, nitrofen, nitrofluorfen, nipiraclofen, neburon, norflurazon norflurazon), noruron (noruron), barban (barban), paclobutrazol (paclobutrazol), paraquat (paraquat), parafluron (parafluron), haloxydine (haloxydine), haloxifene (halauxifen), haloxyfop (haloxyfop), haloxyfop-P (haloxyfop-P), haloxyfop-methyl (haloxyfop-methyl), halosafen (halosafen), halosulfuron (halosulfuron), halosulfuron-methyl (halosulfuron-methyl), bialafos (bilanafos), bixlozone (bixlozone), picloram (picloram), picolinafen (picolinafen), bicyclopyrone (bicyclopyrone), bispyribac (bispyribac), bispyribac-sodium (bispyribac-sodium), pydanon (pydanon), Pinoxaden, bipyrazone, bifenox, piperophos, hymexazol, pyraquinate,Pyraclonil, pyrasulfotole, pyrazoxyfen, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazolate, bilanafos, pyraflufen, pyraflufen-ethyl, pyriclor, pyridafol, pyrithio Pyrithiobac, pyrithiobac-sodium, pyridate, pyriftalid, pyributicarb, pyriflubenzoxim, pyribenzoxim, pyrimisulfan, pyrimisulfuron, pyriminobac-methyl, pyroxasulfone asulfone), pyroxsulam, fenasulam, phenisopham, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, phenothiol, fenoprop, phenobenzuron , feproxydim, fenquinotrione, fenthiaprop, fenteracol, fentrazamide, phenmedipham, phenmedipham-ethyl, fenpyrazone, butachlor, butafenacil, butamifos,Buthiuron, buthidazole, butyrate, buturon, butenachlor, butoxydim, butralin, butroxydim, flazasulfuron, flamprop, furyloxyfen, prynachlor, primisulfuron-methyl fluazifop-methyl), fluazifop, fluazifop-P, fluazifop-butyl, fluazolate, fluchloraminopyr, flufenazopyr, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flu Flurochloridone (flurochloridone), fluorodifen (fluorodifen), fluoronitrofen (fluoronitrofen), fluoromidine (fluoromidine), flucarbazone (flucarbazone), flucarbazone - sodium (flucarbazone-sodium), fluchloralin (fluchloralin), flusulfinam (flusulfinam), flucetosulfuron (flucetosulfuron), fluthiacet (fluthiacet), fluthiacet-methyl (fluthiacet-methyl), flupyrsulfuron (flupyrsulfuron), flufenauxirim (flufenauxirim), flufenauxirim-metotyl (flufenauxirim-metotyl), flufenacet (flufenacet), flufenican (flufenican), flufenoximacil (flufenoximacil), flufenpyr (flufenpyr), flupropacil (flupropacil), flupropanate (flupropanate),Flupoxam, flumioxazin, flumiclorac, flumiclorac-pentyl, flumipropyn, flumezin, fluometuron, flumetsulam, fluridone, flurtamone, fluroxypyr, pretilachlor, proxan, proglinadin, broclozone, prochlorosulfone, procyazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine ), propanil, propyzamide, propisochlor, prohydrojasmon, propyrisulfuron, propham, profluazol, profluralin, prohexadione-calcium, propoxycarbazone, propoxycarbazone-na Thorium (propoxycarbazone-sodium), profoxydim, bromacil, brompyrazone, prometryn, prometon, bromoxynil, bromofenoxim, bromobutide, bromobonil, florasulam, florpyrauxifen,Hexachloroacetone, hexazinone, petoxamid, benazolin, penoxsulam, pebulate, beflubutamid, beflubutamid-M, vernolate, perfluidone, bencarbazone, benquitrione, benzadox, benzipram, benzylaminopurine, benzthiazuron, benzfendizone, bensulide ulide), bensulfuron-methyl, benzoylprop, benzobicyclon, benzofenap, benzofluor, bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine, fomesafen, foramsulfuron, forchlorfenuron, maleic hydrazide hydrazide), mecoprop (mecoprop), mecoprop-P (mecoprop-P), medinoterb (medinoterb), mesosulfuron (mesosulfuron), mesosulfuron methyl (mesosulfuron-methyl), mesotrione (mesotrione), mesoprazine (mesoprazine), mesoprothrin (methoprotryne), metazachlor (metazachlor), methazole (methazole),Metazosulfuron, methabenzthiazuron, metamitron, metamifop, metam, methalpropalin, methiuron, methiozolin, methiobencarb, methyldymron, metoxuron, metosulam, metsulfuron, metsulfuron-methyl yl), metflurazon, metproxybicyclone, 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, lancotrione, rimisoxafen, linuron, rimsulfuron, lenacil, rhodethanil, calcium peroxide, and methyl bromide.

[0152] In addition, 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 nematicides such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, and Pasteuria penetrans; and pesticides such as Trichoderma lignorum, Agrobacterium radiobactor, and non-pathogenic Erwinia carotovora. Similar effects can be expected by mixing it with microbial pesticides used as fungicides, such as Bacillus carotovora and Bacillus subtilis, or biological pesticides used as herbicides, such as Xanthomonas campestris.

[0153] Furthermore, as biological pesticides, for example, natural enemies of Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusa sibirica, Phytoseiulus persimilis, Amblyseius cucumeris, Orius sauteri, and the like, and Beauveria brongniartii, It is also possible to use the compound in combination with a microbial pesticide such as Erythritol brongniartii, or a pheromone agent 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, or 14-methyl-1-octadecene.

[0154] Further, examples of biological pesticides include Agrobacterium spp. such as Agrobacterium radiobacter strain K84 (e.g., "Galltrol-A (registered trademark)" manufactured by AgBioChem, CA), Agrobacterium radiobacter strain K1026 (e.g., "Nogall (registered trademark)" manufactured by Becker Underwood, US), and Agrobacterium radiobacter strain 84 (e.g., "Bacteroses (registered trademark)" manufactured by Nippon Nohyaku Co., Ltd.); Ampelomyces quisqualis strain AQ10 (e.g., "AQ Ampelomyces sp., such as Aspergillus flavus (e.g., Afla-Guard® from Syngenta) and Aspergillus flavus strain AF36 (e.g., AF36® from Arizona Cotton Research and Protection Council, US); Aureobasidium spp., such as a mixture of blastospores of Aureobasidium pullulans strain DSM 14940 and blastospores of strain DSM 14941 (e.g., Botector® from bio-ferm, GmbH); Bacillus amyloliquefaciens amyloliquefaciens strain AT-332 (e.g., "Impression Clear (registered trademark)" manufactured by Idemitsu Agri Co., Ltd.), Bacillus amyloliquefaciens strain B246 (e.g., "University ofPretoria), Bacillus amyloliquefaciens strain D747 (e.g., Bacstar (registered trademark) from Etec Crop Solutions, NZ), Bacillus amyloliquefaciens strain DB101 (e.g., Shelter (registered trademark) from Dagutat Bio lab, ZA), Bacillus amyloliquefaciens strain DB102 (e.g., Artemis (registered trademark) from Dagutat Bio lab, ZA), Bacillus amyloliquefaciens strain amyloliquefaciens strain FZB42 (e.g., RhizoVital® from ABiTEP, DE), Bacillus amyloliquefaciens strain GB03 (e.g., Kodiak® from Bayer Crop Science AG, DE), Bacillus amyloliquefaciens strain MBI600 (e.g., Subtilex® from Becker Underwood, US), Bacillus cepacia (e.g., Deny Stine® from Microbial Products), Bacillus cereus strain BP01 (e.g., Mepichlor® from Arysta, US), Bacillus firmus strain I-1582 (e.g., BioNeem® manufactured by AgoGreen), Bacillus laterosporus (e.g., Bio-Tode® manufactured by Agro-Organics, SA), Bacillus licheniformis strain SB3086 (e.g., EcoGuard® manufactured by Novozymes),Biofungicide®), Bacillus maroccanus (e.g., from Micro Flo Company), Bacillus megaterium strain YFM3.25 (e.g., Bioarc® from BioArc), Bacillus metiens (e.g., from Micro Flo Company), Bacillus mycoides isolate J. (e.g., BmJ® from Certis USA), Bacillus popilliae (e.g., Cronox® from Bio-Crop, CO), Bacillus pumilus strain BU F-33 (e.g., Integral® from Becker Underwood, US), F-33 ​​(registered trademark)), Bacillus pumilus strain GB34 (e.g., Yield Shield (registered trademark) manufactured by Bayer CropScience AG, DE), Bacillus pumilus strain QST2808 (e.g., Sonata (registered trademark) manufactured by Bayer CropScience LP, US), Bacillus simplex strain CGF2856 (e.g., Momihope Wettable Powder (registered trademark) manufactured by Arista LifeSciences Co., Ltd.), Bacillus sphaericus, particularly serotype H5a5b strain 2362 (e.g., VectoLex (registered trademark) manufactured by Valent BioSciences, US), Bacillus subtilis subtilis (e.g., "Botokilla Wettable Powder (registered trademark)" manufactured by Idemitsu Agri Co., Ltd.), Bacillus subtilis var. amyloliquefaciens strain FZB24 (e.g., "Taegro (registered trademark)" manufactured by Novozyme Biologicals, Inc. US), BacillusBacillus subtilis strain QST713 / AQ713 (e.g., "SERENADE MAX (registered trademark)" manufactured by Bayer CropScience LP, US), Bacillus subtilis strain AQ30002 (e.g., "Serenade-DPZ (registered trademark)"), Bacillus subtilis strain D747 (e.g., "Ecoshot (registered trademark)" manufactured by Kumiai Chemical Co., Ltd.), Bacillus subtilis strain HAI-0404 (e.g., "Agrocare Wettable Powder (registered trademark)" manufactured by Nisso Green Co., Ltd.), Bacillus subtilis strain MBI600 (e.g., "Botpica Wettable Powder (registered trademark)" manufactured by Idemitsu Kosan Co., Ltd.), Bacillus subtilis strain Y1336 (for example, "Batistar Wettable Powder (registered trademark)" manufactured by Arista Life Sciences Co., Ltd.), Bacillus thuringiensis strain AM65-52 (for example, "VectoBac (registered trademark)" manufactured by Valent BioSciences, US), Bacillus thuringiensis israelensis strain BMP144 (for example, "Aquabac (registered trademark)" manufactured by Becker Microbial Products IL), Bacillus thuringiensis subspec. Kurstaki strain BMP 123 (for example, manufactured by Becker Microbial Products, IL), Bacillus thuringiensis Kurstaki strain HD-1 (for example, manufactured by Valent BioSciences, US), "Dipel ES®" manufactured by Bayer BioSciences, US), Bacillus thuringiensis subsp. aizawai strain ABTS-1857 (SD-1372, e.g., manufactured by Bayer Crop Science AG,Examples of suitable Bacillus thuringiensis strains include Bacillus thuringiensis subsp. aizawai serotype H-7 (e.g., Florbac WG® manufactured by Valent BioSciences, US), Bacillus thuringiensis subsp. aizawai strain GC-91, Bacillus thuringiensis subspecies. Aegypti (e.g., Agerin®), Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428, e.g., Novodor® manufactured by BioFa DE), ...sp. aegypti (e.g., Agerin®), Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428, e.g., Novodor® manufactured by BioFa DE), Bacillus thuringiensis subsp. aizawai serotype H-7 (e.g., Florbac WG® manufactured by Valent BioSciences, US), Bacillus thuringiensis subsp. aizawai Bacillus spp. such as Bacillus thuringiensis var. 7216 (e.g., "Amactic" and "Pethian"), Bacillus thuringiensis var. T36 (e.g., "Cahat"), Bacillus thuringiensis var. Colmeri (e.g., "TianBaoBTc" from Changzhou Jianghai Chemical Factory), and Bacillus thuringiensis var. san diego (e.g., "M-One" from Bacillus thuringiensis var. san diego); Beauveria bassiana Beauveria bassiana strain (e.g., Naturalis® from Intrachem Bio Italia), Beauveria bassiana strain CG716 (e.g., BoveMax® from Novozymes), Beauveria bassianaBeauveria spp. such as Beauveria bassiana strain F-263 (e.g., Biolisa Madara® manufactured by Idemitsu Kosan Co., Ltd.), Beauveria bassiana strain GHA (e.g., Botaniguard Wettable Powder® manufactured by ARYSTA), and Beauveria brongniartii (e.g., Beaupro® manufactured by Andermatt Biocontrol AG); Bradyrhizobium japonicum (e.g., Optimize® manufactured by Novozymes); Burkholderia spp. strain A396 (e.g., MBI-206 TGAI® manufactured by Marrone Bio Innovations); Candida oleophila Candida spp. such as Candida oleophila strain I-82 (e.g., Aspire® manufactured by Ecogen Inc., US), Candida oleophila strain O (e.g., Nexy® manufactured by BioNext), Candida saitoana (e.g., Biotechnology Research And Development Corporation), and Candida saitoana (e.g., BIOCURE® manufactured by Micro Flo Company, US (BASF SE)); Chaetomium spp. such as Chaetomium cupreum (e.g., BIOKUPRUM™ manufactured by AgriLife) and Chaetomium globosum (e.g., Rivadiom® manufactured by Rivale); sp.); Chromobacterium subtsugae strain PRAA4-1T (MBI-203, e.g., "Marrone Bio");Chromobacterium sp. such as Grandevo® from Innovations); Cladosporium cladosporioides (e.g., Cladosporium cladosporioides); Clonostachys rosea f. catenulate strain J1446 (e.g., PRESTOP® from Verdera, Finland); Colletotrichum gloeosporioides (e.g., Collego® from Agriultural Research Initiatives); Coniothyrium minitans strain CON / M / 91-08 (e.g., Encore® from Encore); Coniothyrium spp. such as Contans® from Anchor Bio-Technologies, LLC; Cryptococcus albidus (e.g., YieldPlus® from Anchor Bio-Technologies, ZA); Delftia acidovorans strain RAY209 (e.g., BioBoost® from Brett Young Seeds); Dilophosphora alopecuri (e.g., Twist Fungus®); Drechsrela sp. such as Drechsrela monoceras strain MTB-951 (e.g., Tasmart Herbicide® from Mitsui Chemicals Agro, Inc.); Entomophthora virulenta virulenta (e.g., "Vektor (registered trademark)" manufactured by "Ecomic"); Fusarium oxysporum strain 101-2 (e.g., "Marcalite" manufactured by "Eisai Seikaken Co., Ltd."); Fusarium oxysporumFusarium spp. such as Gliocladium catenulatum strain J1446 (e.g., Prestop® from AgBio Inc.) and Gliocladium roseum strain 321U (e.g., from WF Stoneman Company LLC); Hirsutella thompsonii (e.g., Mycohit® and ABTEC® from Agro Bio-tech Research Centre, IN); Lactobacillus acidophilus (e.g., Inagrosa-Industrias Agrobiologicas, Lactobacillus sp. such as Lactobacillus plantarum strain BY (e.g., "Fruitsan®" manufactured by "Bayer SA"), Lactobacillus plantarum strain BY (e.g., "Lactoguard Wettable Powder" manufactured by "Meiji Seika Pharma Co., Ltd."), Lactobacillus sp. (e.g., "Lactoplant®" manufactured by "LactoPAFI"); conidia of Lecanicillium lecanii strain KV01 (e.g., "Mycotal®" manufactured by "Koppert / Arysta"); Metarhizium anisopliae strain F52 (e.g., "BIO 1020®" manufactured by "Bayer CropScience"), Metarhizium anisopliae anisopliae strain SMZ-2000 (for example, "Pirate Granules (registered trademark)" manufactured by Arista Life Sciences Co., Ltd.), Metarhizium anisopliae var. acridum (for example, "BiologicalMetarhizium spp. such as Metarhizium anisopliae var. acridum (e.g., GreenGuard® from Becker Underwood, US), Metschnikowia fructicola (e.g., Shemer® from Bayer CropScience), Microdochium dimerum (e.g., ANTIBOT® from Agrauxine, France), Microsphaeropsis ochracea (e.g., Microx® from Prophyta), Monacrosporium phymatopagum, and others. phymatopagum (Nemahiton® manufactured by Tomoe Chemical Industry Co., Ltd.); Mucor haemelis (e.g., BioAvard® manufactured by Indore Biotech Inputs & Research); Myrothecium verrucaria strain AARC-0255 (e.g., DiTera™ manufactured by Valent Biosciences); Ophiostoma piliferum strain D97 (e.g., Sylvanex); Paecilomyces fumosoroseus strain apopka 97 (e.g., PreFeRal® WG manufactured by Biobest), Paecilomyces fumosoroseus strain FE 9901 (e.g., No Fly® manufactured by Natural Industries Inc. (a Novozymes company)), Paecilomyces fumosoroseusPaecilomyces species such as Paecilomyces fumosoroseus (e.g., Preferred Wettable Powder manufactured by Tokai Bussan Co., Ltd.), Paecilomyces lilacinus strain 251 (e.g., BioAct WG (registered trademark) manufactured by Prophyta), compositions containing Paecilomyces lilacinus (e.g., MELOCON (registered trademark)), Paecilomyces tenuipes strain T1 (e.g., Gotz A (registered trademark) manufactured by Idemitsu Kosan Co., Ltd.), and Paecilomyces variotii strain Q-09 (e.g., Nemaquim (registered trademark) manufactured by Quimia, MX). Paenibacillus spp., such as Paenibacillus polymyxa strain AC-1 (e.g., Topseed® manufactured by Green Biotech Company Ltd.) and Paenibacillus poppiliae (e.g., Milky spore disease® manufactured by St. Gabriel Laboratories); Pasteuria spp., such as Pasteuria nishizawa (e.g., Clariva®), Pasteuria nishizawae (e.g., oyacystLF / ST® manufactured by Pasteuria Bioscience), and Pasteuria penetrans (e.g., Pasteuria® manufactured by Pasteuria Bioscience). spp.); Pectobacterium carotovorum (for example, "Biokeeper (registered trademark)" manufactured by Nissan Chemical Industries, Ltd.), Pectobacterium carotovorumPectobacterium spp. such as Pectobacterium carotovorum strain CGE234M403 (e.g., Ecomate® from Kumiai Chemical Co., Ltd.); Penicillium bilaii strains (e.g., Jump Start® from Novozymes); Phlebiopsis gigantea strain FOC PG B22 / SP1190 / 3.2 (e.g., ROTSOP® from Verdera, Finland); Phoma macrostroma strain 94-44B (e.g., Phoma H® from Scotts, US); Pochonia chlamydosporia var. catenulata (e.g., The National Center for Animal and Plant Sciences, University of California, San Diego, CA); Pseudomonas aureofaciens strain TX-1 (e.g., Spot-Less Biofungicide® from EcoSoils Systems, CA), Pseudomonas chlororaphis strain 63-28 (e.g., ATEze® from EcoSoil Systems), Pseudomonas chlororaphis strain MA 342 (e.g., Cedomon® from Bioagri,S), Pseudomonas fluorescens strain 1629RS (e.g., Frostban D® from Frost Technology Corp), Pseudomonas Pseudomonas fluorescens strain A506 (e.g., "Blightban®" manufactured by "Blightban"), Pseudomonas fluorescensPseudomonas fluorescens strain FPT-9601 (for example, "Konae Fukudo (registered trademark)" manufactured by Taki Chemical Co., Ltd.), a mixture of Pseudomonas fluorescens strain FPT-9601 and strain FPH-9601 (for example, "Cellnae Genki (registered trademark)" manufactured by Taki Chemical Co., Ltd.), Pseudomonas fluorescens strain G7090 (for example, "Vegi Keeper (registered trademark)" manufactured by Arysta Life Sciences Co., Ltd.), Pseudomonas proradix (for example, [Proradix (registered trademark]] manufactured by Sourcon Padena), Pseudomonas resinovorans (for example, "Solanacure (registered trademark)" manufactured by Agricultural Research Council, SA), Pseudomonas syringae Pseudomonas spp. such as Pseudomonas syringae strain MA-4 (for example, "Biosave (registered trademark)" manufactured by EcoScience, US), Pseudomonas syringae strain 742RS (for example, "Frostban C" manufactured by Frost Technology Corp (registered trademark)), Pseudomonas rhodesiae strain HAI-0804 (for example, "Masterpiece Wettable Powder (registered trademark)" manufactured by Nippon Soda Co., Ltd.), and Pseudomonas sp. strain CAB-02 (for example, "Momigenki Wettable Powder" manufactured by Nissan Chemical Industries, Ltd.); Pseudomonas aphidis (for example, manufactured by Yissum Research Development Company of the Hebrew University of Jerusalem), Pseudozyma flocculosa flocculosa strain PF-A22 UL (e.g., Sporodex L (registered trademark) manufactured by Plant Products Co. Ltd, CA)sp.); Pythium oligandrum strain DV74 or M1 (e.g., Polyversum® from Bioprepraty, CZ); Reynoutria sachlinensis (e.g., REGALIA® from Marrone BioInnovations, US); Rhizopogon spp., such as Rhizopogon amylopogon (e.g., Myco-Sol® from Helena Chemical Company), Rhizopogon fulvigleba (e.g., Myco-Sol® from Helena Chemical Company); Saccharomyces cerevisiae strains (e.g., Lesaffre et Compagnie, FR); Sclerotinia minor (e.g., Sarritor® from Agrium Advanced Technologies); Serratia entomophila (e.g., Invade® from Wrightson Seeds); Sporothrix insectorum (e.g., Sporothrix Es® from Biocerto;BR); Stagonospora phaseoli (commercially available, for example, from Syngenta); Streptomyces acidiscabies strain RL-110T (e.g., MBI-005EP® from Marrone Bioinnovations, CA); Streptomyces candidus candidus strain Y21007-2 (e.g., BioBac® manufactured by Biontech, TW), Streptomyces galvusStreptomyces spp. such as Streptomyces galbus strain K61 (for example, Mycostop (registered trademark) manufactured by Verdera), Streptomyces lydicus strain WYEC108 (for example, ACTINOVATE (registered trademark) manufactured by Natural Industries, US), and Streptomyces saraceticus (for example, Clanda (registered trademark) manufactured by A & A Group (Agro Chemical Corp.)); Talaromyces flavus strain B-422 (for example, Momikeeper (registered trademark) manufactured by Central Glass Co., Ltd.), Talaromyces flavus Talaromyces spp. such as Talaromyces flavus strain SAY-Y-94-01 (e.g., Toughblock® manufactured by Idemitsu Kosan Co., Ltd.), Talaromyces flavus strain V117b (e.g., PROTUS® WG manufactured by Prophyta, DE); Thiobacillus sp. (e.g., Cropaid® manufactured by Cropaid Ltd, UK); Trichoderma album (e.g., the product known as Bio-Zeid), Trichoderma asperellum strain ICC 012 (e.g., manufactured by Isagro), Trichoderma asperellum strain T34 (e.g., T34® manufactured by Biocontrol Technologies, ES). Biocontrol®), Trichoderma asperellum strain SKT-1 (for example, ECO-HOPE® manufactured by Kumiai Chemical Industry Co., Ltd.), Trichoderma atroviride strain (for example, Esquive® WP manufactured by Agrauxine, FR), Trichoderma atrovirideTrichoderma atroviride strain LC52 (e.g., Tenet® from Agrimm Technologies Ltd, NZ), Trichoderma atroviride strain SKT-1 (e.g., Ecohope DJ® from Kumiai Chemical Industry Co., Ltd.), Trichoderma gamsii strain ICC 080 (e.g., BIO-TAM™ from Bayer Crop Science LP, US), Trichoderma harzianum strain DB 103 (e.g., T-Gro 7456® from Dagutat Biolab), Trichoderma harzianum strain ITEM908 (e.g., Trianum-P® from Koppert), Trichoderma Trichoderma harzianum strain KD (e.g., Trichoplus® from Biological Control Products, SA), Trichoderma harzianum strain TH-35 (e.g., ROOT PRO® from Mycontrol Ltd.), Trichoderma harzianum rifai strain T-22 (KRL-A G2, e.g., PLANTSHIELD T-22G® from Firma BioWorks Inc. US), Trichoderma harzianum rifai strain T-39 (e.g., TRICHODEX® from Makhteshim Ltd, US), Trichoderma lignorum strain TL-0601 (e.g., Futureco Mycotric® manufactured by BINAB Bioscience, ES), Trichoderma polysporum strains (e.g., Binab TF® manufactured by BINAB Bio-Innovation AB, Sweden),Trichoderma spp., such as Trichoderma stromaticum (e.g., TRICOVAB® from Ceplac, Brazil), Trichoderma virens (also known as Gliocladium virens) strain GL-21 (e.g., SOILGARD® from Certis LLC, US), Trichoderma viride strain ICC080 (e.g., REMEDIER® WP from Isagro Ricerca, ITALY), and Trichoderma viride strain TV1 (e.g., Trianum-P® from Koppert); paurometabola strain C-924 (e.g., HeberNem®); Ulocladium oudemansii strain HRU3 (e.g., Botry-Zen® from Botry-Zen Ltd, NZ); Variovorax paradoxus strain CGF4526 (e.g., Field Keeper Wettable Powder® from Central Glass); VA (Vesicular-Arbuscular Mycorrhiza) mycorrhizal fungi (e.g., Dr. Kinkon® from Idemitsu Agri); Verticillium alboatrum strain WCS850 (e.g., Dutch Trig® from Tree Care Innovations), Verticillium lecanii strain IMI Verticillium species such as Verticillium lecanii strain IMI 263817 (for example, Vertalec (registered trademark) manufactured by Arysta LifeScience Co., Ltd.), Verticillium lecanii strain IMI 263817 (for example, Mycotar (registered trademark) manufactured by Arysta LifeScience Co., Ltd.),spp.); Xanthomonas campestris (for example, Camperico Liquid (registered trademark), available from Taki Chemical); and the like can also be used in combination.

[0155] Furthermore, in recent years, IPM (integrated pest management) techniques using insect sex pheromones (such as mating disruptors for tortrix moths and armyworm moths) and natural enemy insects have advanced, and the agent of the present invention can be used in combination with these techniques or as a systematized combination. For example, Mallotus thrips, Anthocoridae thrips, Euonymus isaea, Aphelenchus nigricans, Aphroseius kimurae, Aphroseius gifusa, Aphroseius cucumeri, Aphroseius colemani, Aphelenchus nigricans, Aphelenchus nigricans, Aphelenchus sieboldii, Aphelenchus strigiformes, Aphelenchus strigiformes, Aphelenchus strigiformes, Aphelenchus strigiformes, Aphelenchus degenerans, Trichogramma (bees), Lady beetles, Lady beetles, Aphelenchus sieboldii ... spp.), springtails such as F. candida and A. flavescens (described in "Collembola and Infectious Plant Pathogens (Rhizoctonia spp.)" Chemistry and Biology Vol. 51, No. 4, 2013 pp. 267-269), natural enemies such as the ruby ​​parasite wasp, the Japanese lacewing, the European bigeye wasp, and the Phytoseiulus limonica mite,

[0156] Abreviata caucasica; Acuaria spp.; Agamermis decaudata; Allantonema spp.; Amphimermis spp.; Beddingia siridicola; Bovienema spp.; Cameronia spp.; Chitwoodiella ovofilamenta; Contortylenchus spp.; Culicimermis spp.; Diplotriaena spp.; Empidomermis spp. spp.); Filipjevimermis leipsandra; Gastromermis spp.; Gongylonema spp.; Gynopoecilia pseudovipara; Heterorhabditis bacteriophora (e.g., products known as "B-Green"), Heterorhabditis baujardi, Heterorhabditis heliothidis (e.g., products known as "Nematon"), Heterorhabditis indica, Heterorhabditis malleratus Heterorhabditis spp. such as Heterorhabditis marelatus, Heterorhabditis megidis, and Heterorhabditis zealandica; Hexamermis spp.; Hydromermis spp.); Isomermis spp.; Limnomermis spp.; Maupasina weissi; Mermis nigrescens; Mesomermis spp.; Neomesomermis spp.; Neoparasitylenchus rugulosi; Octomyomermis spp.; Parasitaphelenchus spp.; Parasitorhabditis spp.; Parasitylenchus spp.; Perutilimermis chrysis culicis; Phasmarhabditis hermaphrodita; Physaloptera spp.; Protrellatus spp.; Pterygodermatites spp.; Romanomermis spp.; Seuratum cadarachense; Sphaerulariopsis spp.); Spirura guianensis; Steinernema carpocapsae (e.g., products known as "Biocontrol" and "Biosafe (registered trademark)" manufactured by SDS Biotech Co., Ltd.), Steinernema feltiae (e.g., products known as "Nemasys (registered trademark)"), Steinernema glaseri (e.g., products known as "Biotopia (registered trademark)" and "Biotopia" manufactured by Arista LifeScience Co., Ltd.), Steinernema kraussei (e.g., products known as "Larvesure"), Steinernema Steinernema spp. such as Steinernema kushidai (e.g., "Shibaichinema" manufactured by Kubota Corporation), Steinernema riobrave (e.g., the product known as "Biovector"), Steinernema scapterisci (e.g., the product known as "Nematac S"), Steinernema scarabaei, and Steinernema siamkayai; Strelkovimermis peterseni; Subulura spp.; Sulphuretylenchus elongatus; Tetrameres spp. spp.) and other natural enemy nematodes.

[0157] Tobacco mosaic virus, Adoxophyes orana granulosis virus (GV) (e.g., the product known as "BIOFA-Capex®"), a mixture of Adoxophyes orana granulosis virus (MAFF632001) and tea tortrix granulosis virus (MAFF632002) (e.g., "Tortrix Natural Enemy®" manufactured by Arysta LifeSciences), Agrotis segetum nucleopolyhedrovirus (NPV), Anticarsia gemmatalis (Woolly pyrolus moth) mNPV (e.g., the product known as "Polygen®"), Autographa californica (Alfalfa Looper) mNPV (e.g., the product known as "VPN80®"; supplied by Agricola El Sol), tea looper (Biston suppressaria) NPV, silkworm (Bombyx mori) NPV, Cryptophlebia leucotreta (false codling moth) GV (e.g., the product known as "Cryptex®"), Cydia pomonella spp. such as Cydia pomonella granulosis, viruses, codling moth (Cydia pomonella granulosis virus) (CpGV) (e.g., the product known as "Madex Plus®"), Masson pine moth (Dendrolimus punctatus) CPV (e.g., DVC wettable powder "Matsukemin" manufactured by Chugai Pharmaceutical), Helicoverpa armigera armigera) NPV (e.g., the product known as "AgBiTech-ViVUS Max®"), Helicoverpa zea (formerly Heliothis zea) NPV (e.g., the product known as "Elcar®");Willow tussock moth (Leucoma salicis) NPV, gypsy moth (Lymantria dispar) NPV (e.g., products known as "Gypcheck®"), balsam-fir sawfly (Neodiprion abietis) NPV (e.g., products known as "Abietiv®"), Neodiprion lecontei (red-headed pinesawfly) NPV (e.g., products known as "Lecontvirus®"), pine sawfly (Neodiprion sertifer) NPV (e.g., products known as "Neocheck-S®"), Orgyia pseudotsugata (Douglas-fir tussock moth) NPV (e.g., products known as "Virtuss®"), potato tuber moth (tobacco leaf miner (Phthorimaea operculella) GV (e.g., the product known as "Matapol®"), cabbage white butterfly (Pieris rapae) GV, diamondback moth (Plutella xylostella) GV (e.g., the product known as "Plutec®"), Spodoptera albula (gray-streaked armyworm moth) mNPV (e.g., the product known as "VPN 82®"), true armyworm (Spodoptera exempta) mNPV (e.g., the product known as "Spodec®"), sugarbeet armyworm (Spodoptera exigua) mNPV (e.g., the product known as "Spexit®"; supplier: Andermatt Biocontrol), fall armyworm (Spodoptera frugiperda mNPV (e.g., the product known as "Baculovirus VPN®"), Egyptian armyworm (tobaccocutworm (Spodoptera littoralis) NPV (a product known as "Spodoptrin®"; supplied by NPP Calliope France), oriental leafworm moth (Spodoptera litura) NPV (Littovir®), oriental leafworm moth nuclear polyhedrosis virus Fu-1 strain occlusion bodies ("Hasumon Ten'ei" manufactured by Nippon Kayaku Co., Ltd.), oriental leafworm moth nuclear polyhedrosis virus clone A9 strain and clone C3 strain occlusion bodies (e.g., "Hasumon Killer" manufactured by Ibigawa Kogyo Co., Ltd.), zucchini yellow mosaic virus attenuated strain ZY-02 (e.g., "Kyoto Biken" Cubio ZY-02®" manufactured by Microbial Chemistry Research Institute Co., Ltd.), zucchini yellow mosaic virus attenuated strain ZY-95 antiviral agents such as ketamine (e.g., "Kyoto Biken" Cubic ZY (registered trademark) manufactured by Microbial Chemistry Research Institute, Inc.), and the attenuated strain AVP08 of pepper mild mottle virus (e.g., "Green Pepper PM (registered trademark)" manufactured by Microbial Chemistry Research Institute, Inc.);

[0158] Alumigelua, Uwabarua, Diamolua, Beetarmylua, and Litria agents ("Confuser V (registered trademark)" manufactured by Kyoyu Agri Co., Ltd.), Cure liquid agent (for example, "Cure" (registered trademark) manufactured by Sankei Chemical Co., Ltd.), methyl eugenol agents (for example, "Sankei Methyl Eugenol" (registered trademark) manufactured by Sankei Chemical Co., Ltd.), Shinancelua agent ("Sukashibacon L (registered trademark)" manufactured by Shin-Etsu Chemical Co., Ltd.), Kossinlua agent ("Bokutoukon-H (registered trademark)" manufactured by Shin-Etsu Chemical Co., Ltd.), Totrilua agent ("Hamakikon-N (registered trademark)" manufactured by Shin-Etsu Chemical Co., Ltd.), Oriflua, Totrilua, and Peachflua agents ("Confuser" manufactured by Kyoyu Agri Co., Ltd.), R (registered trademark)), Orifluor, Tortrilua, and Peachfluor agents (Confuser N (registered trademark) manufactured by Shin-Etsu Chemical Co., Ltd.), Orifluor, Tortrilua, Peachfluor, and Pirimal agent (Confuser MM (registered trademark) manufactured by Shin-Etsu Chemical Co., Ltd.), Alimal, Orifluor, Tortrilua, and Peachfluor agent (Confuser AA (registered trademark) manufactured by Shin-Etsu Chemical Co., Ltd.), Masinissal agent (Hetamushikon (registered trademark) manufactured by Shin-Etsu Chemical Co., Ltd.), Fallwebure agent (Nitorure Ameshiro (registered trademark) manufactured by Idemitsu Kosan Co., Ltd.), Kerquibor agent (Kashinagacol (registered trademark) manufactured by Sankei Chemical Co., Ltd.), Bulware and Loucaria agents (for example, Confuser G (registered trademark)"), MEP Sweetvirua granules (Arimodoxicol granules (registered trademark) manufactured by Sankei Chemical Co., Ltd.), Inferua (Yutaka-1 (registered trademark) manufactured by Shin-Etsu Chemical Co., Ltd.), Ochimeranorua (e.g., Sankei Ochimeranocol (registered trademark) manufactured by Sankei Chemical Co., Ltd.), Sakineranorua (Sakimeranocol (registered trademark) manufactured by Sankei Chemical Co., Ltd.), Beetarmylua (e.g., Yotaka-S (registered trademark) manufactured by Shin-Etsu Chemical Co., Ltd.), Litria (e.g., Ferrodin SL (registered trademark) manufactured by Sumitomo Chemical Co., Ltd.), Diamolua (e.g., Konagacon (registered trademark) manufactured by Sankei Chemical Co., Ltd.), and other pheromone agents;

[0159] Acacia negra extract, abscisic acid, Chenopodium ambrosiodae extract, arginine, alginate oligosaccharide, Nepitella oil, eugenol, L-carvone, ethyl formate, chitin, chitosan (e.g., "BotriZen Ltd.,"ARMOUR-ZEN" manufactured by "NZ", Quillaya Extract, Ginkgo biloba components selected from the group consisting of Ginkgolide A, Ginkgolide B, Ginkgolide C, Ginkgolide J, and Ginkgolide M, Grapefruit seed and pulp extract, potassium silicate, cytokinin, sanguinarine (derived from bamboo rush), cis-Jasmone, citral, gibberellin derivative, siccanin (a substance produced by the ryegrass leaf spot fungus Helminthosporium siccans), citronella oil Oil, Citronellol, Jasmonic acid, Methyl Jasmonate, Sorbitol actanoate, Neem tree (extracts from seeds of the neem tree), Neem Oil, Thymol, Terpinolene, Synthetically produced terpenes from extract of Chenopodium ambrosioides near ambrosioides (which contains a mixture of three terpenes, namely α-terpinene, p-cymene, and limonene, as pesticidal active ingredients) (e.g., the product known as "Requiem®"; supplied by Bayer CropScienceLP,US, bilobalide, humic acid and fulvic acid extracted from lignite clay forms, pentatermanone, marigold oil, isopropyl myristate, methyl eugenol, methyl jasmonate, harpin protein, heptyl butyrate, lavandulyl senecioate, lignite clay known as leonardite, Humates such as (E,Z)-7,9-dodecadien-1-yl acetate, (E,Z)-2,4-ethyldecadienoate (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, 2-methyl-1-butanol, (E,Z)-2,13-octadecadien-1-ol, (E,Z)-2,13-octadecadien-1-ol acetate, (E,Z)-3,13-octadecadien-1-ol, R-1-octen-3-ol, (E,Z,Z)-3,8,11-tetradecatrienyl acetate, (Z,E)-9,12-Tetradecadien-1-yl acetate, Z-7-tetradecen-2-one, Z-9-tetradecen-1-yl acetate, Z-11-tetradecenal, Z-11-tetradecen-1-ol, plumbagin, a plant extract component from the genera Pongamia, Calotropis, Plumbago, Maytenus, Baccharis, Rubia, Calophyllum, Urtica, Kobresia, and Caesalpinia, Rhodopseudomonas speroides It is also possible to use in combination with extracts from organisms such as brassinosteroids produced by Bacillus speroides, in particular strain IFO-12203; harpins isolated by Erwinia amylovora (Harpin protein); for example, products known as "Harp-N-Tek®", "Messenger®", "Employ®", and "ProAct®".

[0160] The present invention will be explained in more detail below with reference to examples of the production of representative compounds and intermediates, but the present invention is not limited to these examples. In the examples below, "mmol" means millimoles, and the figure (%) in parentheses after the amount obtained indicates the yield.

[0161] Example 1. Preparation of ethyl 2-(4-(tert-butyl)phenyl)-3-methylbutanoate [β] Isopropyl iodide (9.3 g, 54 mmol) was added to a solution of ethyl 2-(4-(tert-butyl)phenyl)acetate [α] (10 g, 45 mmol) in dimethylacetamide (50 mL), and the mixture was stirred in an ice bath for 10 minutes. Sodium hydride (2.2 g, 54 mmol) was slowly added in portions, and the mixture was stirred overnight while gradually warming to room temperature. After completion of the reaction, a saturated aqueous ammonium chloride solution was added to terminate the reaction, and the mixture was extracted with t-butyl methyl ether. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 11 g of ethyl 2-(4-(tert-butyl)phenyl)-3-methylbutanoate [β] (yield: 78%).

[0162] Example 2. Preparation of 2-(4-(tert-butyl)phenyl)-3-methylbutanoic acid [γ] (racemic form) To an ethanol solution (63 mL) of ethyl 2-(4-(tert-butyl)phenyl)-3-methylbutanoate [β] (11 g, 42 mmol), 2 M aqueous sodium hydroxide solution (63 mL, 0.13 mol) was added, and the mixture was stirred under reflux for 5 hours. After completion of the reaction, the mixture was concentrated under reduced pressure to remove the ethanol, and 1 M hydrochloric acid was added to make the mixture acidic. The resulting solution was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 10 g (quantity) of 2-(4-(tert-butyl)phenyl)-3-methylbutanoic acid [γ].

[0163] Example 3. Preparation of optically active 2-(4-(tert-butyl)phenyl)-3-methylbutanoic acid [γ] To a solution of 4-(1,1-dimethylethyl)-α-(1-methylethylidene)phenylacetic acid (0.27 g, 1.1 mmol) in methanol (20 mL), catalyst A (CAS Registry Number: 913829-90-0), 37.6 mg, 0.021 mmol), and triethylamine (0.15 mL, 1.1 mmol) were added, and the mixture was stirred at 60°C under a hydrogen atmosphere (10-11 atm) for 6 hours. After completion of the reaction, the mixture was returned to room temperature and, under an air atmosphere, the methanol was removed by distillation under reduced pressure. 0.6 M aqueous HCl was added to terminate the reaction, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain optically active 2-(4-(tert-butyl)phenyl)-3-methylbutanoic acid [γ] (0.30 g) as a crude product.

[0164] Example 4. Preparation of Compound No. IA-32 To a tetrahydrofuran solution (0.1 L) of 2-(4-(tert-butyl)phenyl)-3-methylbutanoic acid [γ] (4 g, 17 mmol) synthesized in Example 2, 4-dimethylaminopyridine (0.21 g, 1.7 mmol), (5,6-dimethylpyridin-2-yl)methanamine dihydrochloride (4.6 g, 22 mmol), triethylamine (6.9 g, 68 mmol), and 2-chloro-N-methylpyridinium iodide (8.7 g, 34 mmol) were added, and the mixture was stirred under reflux for 8 hours. After completion of the reaction, water was added to quench the reaction, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 5.0 g (yield: 82%) of 2-(4-(tert-butyl)phenyl)-N-((5,6-dimethylpyridin-2-yl)methyl)-3-methylbutanamide [I-A-32].

[0165] Example 5. Preparation of Compound No. I-G-4 (optically active substance) To a tetrahydrofuran solution (1.8 ml) of 2-(4-(tert-butyl)phenyl)-3-methylbutanoic acid [γ] (51 mg, 0.22 mmol) synthesized in Example 3, 4-dimethylaminopyridine (8.3 mg, 0.068 mmol), (5,6-dimethylpyridin-2-yl)methanamine dihydrochloride (57 mg, 0.27 mmol), triethylamine (0.15 ml, 1.0 mmol), and 2-chloro-N-methylpyridinium iodide (94 mg, 0.42 mmol) were added, and the mixture was stirred under reflux for 3 hours. After completion of the reaction, water was added to quench the reaction, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 34 mg of 2-(4-(tert-butyl)phenyl)-N-((5,6-dimethylpyridin-2-yl)methyl)-3-methylbutanamide [I-G-4] (yield: 43%, 2 steps, 60% ee). The asymmetric yield was determined using a chiral column (CHIRALPAK® AS-RH (manufactured by Daicel Corporation), 4.6 mm x 150 mm, 5 μm, detector: 220 nm), at a column temperature of 35°C and a mobile phase flow rate of 1 mL / min (5 mM Ammonium Acetate in H ２ The measurement was carried out under the condition of (a) 2H2O / MeCN=400 / 600 (v / v) and the peaks at retention times of 3.7 min ([IG-3]) and 4.5 min ([IG-4]) were calculated as the respective optical isomers.

[0166] Examples of formulations are shown below, but the invention is not limited to these. In the formulation examples, "parts" means parts by weight.

[0167] Formulation Example 1 Compound [I] of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above ingredients are mixed and dissolved uniformly to prepare an emulsifiable concentrate.

[0168] Formulation Example 2 Compound [I] of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above ingredients are uniformly mixed and pulverized to give a dust.

[0169] Formulation Example 3 Compound [I] of the present invention 5 parts Mixed powder of bentonite and clay 90 parts Calcium lignosulfonate 5 parts The above ingredients are uniformly mixed, and an appropriate amount of water is added, followed by kneading, granulation and drying to give granules.

[0170] Formulation Example 4 Compound [I] of the present invention 20 parts Kaolinite and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above ingredients are uniformly mixed and pulverized to give a wettable powder.

[0171] Formulation Example 5 Compound [I] of the present invention 10 parts Mixture of nonionic and anionic surfactants ("Sorpol 3105" (Toho Chemical Industry Co., Ltd.)) 5 parts Propylene glycol 2 parts Xanthan gum 1 part Water 82 parts Manufacturing method: The ingredients other than water are uniformly mixed and dispersed in water to give a flowable preparation.

[0172] Test examples of the present invention are shown below, but the present invention is not limited to these.

[0173] Test Example 1. Test of efficacy in controlling black spot disease of Chinese cabbage A formulation prepared according to Formulation Example 1 containing the compound of the present invention was diluted to a predetermined amount with water. 10 ml of the solution was sprayed on the stems and leaves of Chinese cabbage (variety: Musou) at the 3- to 5-leaf stage grown in a 5 cm diameter pot. After air-drying the solution, a spore suspension of the Chinese cabbage black spot fungus was sprayed and inoculated. The plants were kept at a temperature of 20°C under humid conditions for one day, then moved to a greenhouse and allowed to develop disease. Five days after inoculation, activity was determined according to the following calculation formula:

[0174] Judgment criteria 0: Control value 9% or less 1: Control value 10-19% 2: Control value 20-29% 3: Control value 30-39% 4: Control value 40-49% 5: Control value 50-59% 6: Control value 60-69% 7: Control value 70-79% 8: Control value 80-89% 9: Control value 90-99% 10: Control value 100%

[0175] As a result of the above test, at a concentration of 50 ppm, the compounds I-A-4, I-A-14, I-A-15, I-A-27, I-A-50, I-A-51, I-A-53, I-A-54, I-A-57, I-A-61, I-A-63, I-A-64, I-A-65, I-A-69, I-A-70, I-A-71, I-A-72, I-A-73, I-A-74, I-A-80 and I-A-85 showed activity of criterion 8 or higher.

[0176] Test Example 2. Test of control effect against cucumber Botrytis cinerea A formulation prepared according to Formulation Example 1 containing the compound of the present invention was diluted with water to a predetermined amount. 10 ml of the solution was sprayed on the stems and leaves of cucumbers (variety: Yotsuba) at the one-leaf stage grown in a 9 cm diameter pot. After air-drying the solution, a paper disk was placed in the center of the leaf and impregnated with a spore suspension of Botrytis cinerea. The leaves were maintained at a temperature of 15°C and humidity to allow the disease to develop. Five to six days after inoculation, the control effect was evaluated according to the evaluation criteria of Test Example 1.

[0177] As a result of the above test, at a concentration of 50 ppm, I-A-2, I-A-3, I-A-4, I-A-5, I-A-6, I-A-7, I-A-10, I-A-13, I-A-14, I-A-15, I-A-16, I-A-17, I-A-20, I-A -21, I-A-24, I-A-26, I-A-27, I-A-28, I-A-29, I-A-30, I-A-31, I-A-32, I-A-33, I-A-34, I-A-35, I-A-37, I-A-39, I-A-40, I-A-42, I The compounds I-A-44, I-A-48, I-A-49, I-A-50, I-A-51, I-A-52, I-A-53, I-A-54, I-A-55, I-A-57, I-A-60, I-A-61, I-A-62, I-A-63, I-A-64, I-A-66, I-A-67, I-A-69, I-A-70, I-A-71, I-A-74, I-A-80, I-A-85, I-A-87, I-A-88, I-F-1, I-G-1, I-G-2, I-G-3 and I-G-4 showed activity of 8 or more.

[0178] Test Example 3. Test of efficacy in controlling cucumber anthracnose A formulation prepared according to Formulation Example 1 containing the compound of the present invention was diluted with water to a predetermined amount. 10 ml of the solution was sprayed over the stems and leaves of cucumbers (variety: Yotsuba) at the two-leaf stage grown in a 9 cm diameter pot. After air-drying the solution, a spore suspension of the cucumber anthracnose fungus was sprayed and inoculated. After holding at a temperature of 20°C under humid conditions for one day, the plant was moved to a greenhouse and allowed to develop disease. Six days after inoculation, the control efficacy was evaluated according to the evaluation criteria of Test Example 1.

[0179] As a result of the above test, at a concentration of 50 ppm, I-A-1, I-A-2, I-A-3, I-A-4, I-A-5, I-A-6, I-A-7, I-A-8, I-A-9, I-A-10, I-A-13, I-A-14, I-A-15, I-A-16, I-A-17, I-A-18, I-A -20, I-A-21, I-A-22, I-A-23, I-A-24, I-A-25, I-A-26, I-A-27, I-A-28, I-A- 29, I-A-30, I-A-31, I-A-32, I-A-33, I-A-34, I-A-35, I-A-36, I-A-37, I-A-38 , I-A-39, I-A-40, I-A-41, I-A-42, I-A-43, I-A-44, I-A-48, I-A-49, I-A-51, I-A-53, I-A-54, I-A-55, I-A-57, I-A-58, I-A-59, I-A-60, I-A-61, I-A-62, I The compounds I-A-63, I-A-64, I-A-65, I-A-66, I-A-67, I-A-68, I-A-70, I-A-71, I-A-80, I-A-85, I-A-87, I-A-88, I-F-1, I-G-1, I-G-2, I-G-3 and I-G-4 showed activity of 8 or more.

[0180] Test Example 4. Test of rice blast control effect A formulation prepared according to Formulation Example 1 containing the compound of the present invention was diluted to a predetermined amount with water. 10 ml of the solution was sprayed on the foliage of rice plants (variety: Kinmaku) at the 6-7 leaf stage grown in a 6 cm diameter pot. After air drying, a spore suspension of rice blast fungus was sprayed and inoculated. After keeping at a temperature of 20°C under humid conditions for 1 day, the plants were moved to a greenhouse and allowed to develop disease. Six days after inoculation, the control effect was evaluated according to the evaluation criteria of Test Example 1.

[0181] As a result of the above test, at a concentration of 50 ppm, I-A-1, I-A-3, I-A-4, I-A-5, I-A-6, I-A-7, I-A-8, I-A-9, I-A-13, I-A-14, I-A-15, I-A-16, I-A-17, I-A-21, I-A-24, I-A-25, I-A-30, I-A-31, I-A-32, I-A-33, I-A-34, I-A-35, I-A-38, I-A- Compounds I-A-39, I-A-40, I-A-43, I-A-44, I-A-49, I-A-50, I-A-51, I-A-53, I-A-54, I-A-55, I-A-57, I-A-64, I-A-67, I-A-68, I-A-70, I-A-71, I-A-80, I-A-85, I-A-87, I-A-88, I-F-1, I-G-2, I-G-3 and I-G-4 showed activity of 8 or more.

[0182] Test Example 5. Test of apple scab control efficacy A formulation prepared according to Formulation Example 1 containing the compound of the present invention was diluted to a predetermined amount with water. 10 ml of the solution was sprayed on the foliage of apple seedlings (cultivar: Orin) grown in pots with a diameter of 5 cm. After air-drying the solution, a spore suspension of apple scab fungus was sprayed and inoculated. After being kept at 20°C and under humid conditions for 2 days, the plants were moved to a room at 15°C and humidified as needed to promote disease development. 15 days after inoculation, the control efficacy was evaluated according to the evaluation criteria of Test Example 1.

[0183] As a result of the above test, at a concentration of 50 ppm, I-A-1, I-A-2, I-A-3, I-A-4, I-A-5, I-A-6, I-A-7, I-A-8, I-A-9, I-A-10, I-A-13, I-A-15, I-A-16, I-A-17, I-A-18, I-A-19, I-A -22, I-A-23, I-A-24, I-A-25, I-A-26, I-A-27, I-A-28, I-A-29, I-A-30, I-A- 31, I-A-32, I-A-33, I-A-34, I-A-35, I-A-36, I-A-37, I-A-38, I-A-39, I-A-40 , I-A-41, I-A-42, I-A-43, I-A-44, I-A-48, I-A-49, I-A-50, I-A-51, I-A-53, I-A-54, I-A-55, I-A-57, I-A-58, I-A-59, I-A-60, I-A-61, I-A-62, I-A-63, I- Compounds I-A-64, I-A-66, I-A-67, I-A-68, I-A-69, I-A-70, I-A-71, I-A-72, I-A-73, I-A-80, I-A-85, I-A-87, I-A-88, I-G-1, I-G-2, I-G-3 and I-G-4 showed activity of 8 or more.

[0184] Test Example 6. Test of Barley Powdery Mildew Control Effect A formulation prepared according to Formulation Example 1 containing the compound of the present invention was diluted to a predetermined amount with water. 10 ml of the solution was sprayed onto the foliage of barley (variety: Kanto No. 6) at the one-leaf stage grown in a 5 cm diameter pot. After air-drying, barley powdery mildew fungus was sprinkled on top for inoculation. The plants were kept in a greenhouse at 25°C to promote disease development. Seven days after inoculation, the control effect was evaluated according to the evaluation criteria of Test Example 1.

[0185] As a result of the above test, at a concentration of 50 ppm, the compounds I-A-1, I-A-7, I-A-8, I-A-9, I-A-10, I-A-14, I-A-15, I-A-16, I-A-17, I-A-31, I-A-32, I-A-39, I-A-40, I-A-53 and I-A-54 showed an activity of 8 or more.

[0186] Test Example 7. Antibacterial Activity Test Using the following (a), (b), and (c) as test bacteria, the mycelial growth inhibitory activity of each test compound was confirmed using PDA medium. After growth, the diameter of the mycelium was measured, and the median effective concentration (EC ５０ (a) Septoria tritici (b) Fusarium graminearum (c) Sclerotinia sclerotiorum

[0187] Based on the results of the above tests, list the compounds with a half-maximal effective concentration of 50 ppm or less. (a) I-A-3, I-A-5, I-A-6, I-A-7, I-A-14, I-A-15, I-A-24, I-A-30, I-A-32, I-A-53, I-A-54, I-A-58, I-G-2 and I-G-4 (b) I-A-1, I-A-2, I-A-3, I-A-4, I-A-5, I-A-6, I-A-7, I-A-8, I-A-9, I-A-10, I-A-14, I-A-15, I-A-16, I-A-17, I-A-19, I-A-20, I-A-21, I-A-22, I-A-23, I-A-24, I-A-25, I-A-26, I-A-27, I-A-28, I-A-30, I-A-31, I-A-32, I-A-34, I-A-36, I-A-38, I-A-39, I-A-40, I-A-41, I-A-44, I-A-48, I-A-49, I-A-50, I-A-51, I-A-52, I-A-58, I-A-65, I-A-66, I-A-67, I-A-68, I-A-69, I-A-70, I-A-71, I-A-76, I-F-1, I-G-3 and I-G-4 (c) I-A-1, I-A-2, I-A-3, I-A-4, I-A-5, I-A-6, I-A-7, I-A-8, I-A-9, I-A-10, I-A-14, I-A-15, I-A-16, I-A-17, I-A-18, I-A-19, I-A-20, I-A-21, I-A-22, I-A-23, I-A-24, I-A-25, I-A-26, I-A-27, I-A-28, I-A-29, I-A-30, I-A-31, I-A-32, I-A-33, I-A-34, I-A-35, I-A-36, I-A-37, I-A-38, I-A-39, I-A-40, I-A-41, I-A-42, I-A-43, I-A-44, I-A-48, I-A-49, I-A-50, I-A-51, I-A-52, I-A-53, I-A-54, I-A-58, I-A-61, I-A-62, I-A-63, I-A-64, I-A-65, I-A-66, I-A-67, I-A-68, I-A-69, I-A-70, I-A-71, I-A-72, I-A-73, I-A-74, I-A-76, I-A-80, I-G-1, I-G-2, I-G-3 and I-G-4

[0188] The amide compounds according to the present invention have an effect of controlling diseases that occur in grains, fruit trees, vegetables, other crops and flowers, and are therefore useful as agricultural chemicals.

[0189] This application is based on Japanese Patent Application No. 2024-078455 filed on May 14, 2024, the contents of which are incorporated in their entirety herein.

Claims

1. General form [I] {where R is the formula} １ (a1) a (C4-C6) alkyl group; (a2) an iodine atom; (a3) ​​a (C3-C6) alkoxy group; (a4) a halo(C1-C6) alkoxy group; (a5) a (C1-C6) alkylsulfanyl group; (a6) a halo(C1-C6) alkylsulfanyl group; (a7) an aminocarbonyl group; (a8) a Z aminocarbonyl group; (a9) a nitro group; (a10) a cyano group; (a11) a (C1-C6) alkylcarbonyl group; (a12) a Z carbonyl group; (a13) a Z group; (a14) a (C1-C12) alkylsilyl group; (a15) a Z oxy group; (a16) a hydroxy group; (a17) a (C3-C6) cycloalkoxy group; (a18) a halo(C1-C6) alkyl group; (a19) Z carbonyloxy group; (a20) Z amino group; (a21) Z alkyl group; (a22) (C2-C6) alkenyl group; (a23) halo(C2-C6) alkenyl group; (a24) (C2-C6) alkynyl group; (a25) halo(C2-C6) alkynyl group; (a26) (C3-C6) cycloalkyl group; (a27) (C3-C6) cycloalkenyl group; (a28) halo(C3-C6) cycloalkyl group; (a29) (C3-C6) cycloalkyl(C1-C6) alkyl group; (a30) (C3-C6) cycloalkyl(C3-C6) cycloalkyl group; (a31) halo(C3-C6) cycloalkyl(C1-C6) alkyl group; (a32) (a33) a halo(C1-C6)alkylsulfinyl group; (a34) a (C1-C6)alkylsulfonyl group; (a35) a halo(C1-C6)alkylsulfonyl group; (a36) a halo(C3-C6)cycloalkylhalo(C1-C6)alkyl group; or (a37) a methoxy group, and Z is (b1) a phenyl group;(b2) A halogen atom, a nitro group, a cyano group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, a halo(C1-C6)alkoxy group, a (C2-C6)alkenyl group, a halo(C2-C6)alkenyl group, a (C2-C6)alkynyl group, a (C3-C6)cycloalkyl group, a (C2-C6)alkenyloxy group, a halo(C2-C6)alkenyloxy group, a (C1-C6)alkylsulfanyl group, a halo(C1-C6)alkylsulfanyl group, a (C1-C6)alkylsulfonyloxy group, a halo(C1-C6)alkylsulfonyloxy group, a (C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylsulfonyl group, a (C2-C 6) a substituted phenyl group having 1 to 5 substituents independently selected from the group consisting of an alkenylsulfanyl group, a halo(C2-C6)alkenylsulfanyl group, a (C2-C6)alkenylsulfinyl group, a halo(C2-C6)alkenylsulfinyl group, a (C2-C6)alkenylsulfonyl group, a halo(C2-C6)alkenylsulfonyl group, an N-mono(C1-C6)alkylamino group, an N,N-di(C1-C6)alkylamino group in which the alkyl groups may be the same or different, a (C1-C6)alkylsulfonylamino group, a halo(C1-C6)alkylsulfonylamino group, a (C1-C6)alkylcarbonyl group, a halo(C1-C6)alkylcarbonyl group, a (C1-C6)alkoxycarbonyl group, a (C1-C9)alkylsilyl group, and a phenyl group; (b3) a heterocyclic group; or (b4) a substituted heterocyclic group having 1 to 3 substituents independently selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, a halo(C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo(C1-C6) alkoxy group, a (C1-C6) alkylsulfanyl group, a halo(C1-C6) alkylsulfanyl group, a (C1-C6) alkylsulfinyl group, a halo(C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, and a halo(C1-C6) alkylsulfonyl group, ２ (c1) a (C3-C6)alkyl group; (c2) a halo(C2-C6)alkyl group; (c3) a (C3-C6)cycloalkyl(C1-C6)alkyl group; (c4) a cyclopentyl group; (c5) a halocyclopentyl group; (c6) a (C4-C6)alkenyl group; (c7) a hydroxy(C3-C6)alkyl group; (c8) a (C1-C6)alkoxy(C1-C6)alkyl group; (c9) a halo(C1-C6)alkoxy(C1-C6)alkyl group; (c10) a (C3-C6)cycloalkoxy(C1-C6)alkyl group; (c11) a halo(C3-C6)cycloalkoxy(C1-C6)alkyl group; or (c12) a (C1-C6)alkoxy(C1-C6)alkoxy group, and R ３ (d1) a (C1-C6) alkyl group; (d2) a halogen atom; (d3) a halo(C1-C6) alkyl group; (d4) a (C1-C6) alkoxy group; (d5) a halo(C1-C6) alkoxy group; (d6) a cyano group; or (d7) a Z group, or two R ３ are bonded to each other to form a group of the following formula R ３－１ or R ３－２ may form a ring structure represented by X represents an oxygen atom or a sulfur atom, Ar １ represents a phenyl group, a pyrimidinyl group, or a pyridyl group, Ar ２ represents a pyridyl group or a quinolyl group, m represents 1, 2, 3, 4 or 5, and n represents 0, 1, 2, 3, 4 or 5, or a salt thereof.

2. R １ (a1) a (C4-C6) alkyl group; (a2) an iodine atom; (a3) ​​a (C3-C6) alkoxy group; (a4) a halo(C1-C6) alkoxy group; (a5) a (C1-C6) alkylsulfanyl group; (a6) a halo(C1-C6) alkylsulfanyl group; (a11) a (C1-C6) alkylcarbonyl group; (a12) a Z carbonyl group; (a13) a Z group; (a14) a (C1-C12) alkylsilyl group; (a15) a Z oxy group; (a16) a hydroxy group; (a17) a (C3-C6) cycloalkoxy group; (a18) a halo(C1-C6) alkyl group; (a19) a Z carbonyloxy group; (a20) a Z amino group; (a21) a Z alkyl group; (a22) (a24) a (C2-C6) alkenyl group; (a26) a (C3-C6) cycloalkyl group; (a32) a (C1-C6) alkylsulfinyl group; (a34) a (C1-C6) alkylsulfonyl group; or (a37) a methoxy group, and R ２ (c1) a (C3-C6)alkyl group; (c2) a halo(C2-C6)alkyl group; (c3) a (C3-C6)cycloalkyl(C1-C6)alkyl group; (c4) a cyclopentyl group; (c6) a (C4-C6)alkenyl group; (c7) a hydroxy(C3-C6)alkyl group; or (c8) a (C1-C6)alkoxy(C1-C6)alkyl group; and R ３ (d1) a (C1-C6) alkyl group; (d2) a halogen atom; (d3) a halo(C1-C6) alkyl group; (d4) a (C1-C6) alkoxy group; (d5) a halo(C1-C6) alkoxy group; (d6) a cyano group; or (d7) a Z group, or ３ are bonded to each other to form a group of the following formula R ３－２ may form a ring structure represented by The compound or salt thereof according to claim 1.

3. R １ (a1) a (C4-C6) alkyl group; (a2) an iodine atom; (a3) ​​a (C3-C6) alkoxy group; (a4) a halo(C1-C6) alkoxy group; (a6) a halo(C1-C6) alkylsulfanyl group; (a11) a (C1-C6) alkylcarbonyl group; (a12) a Z carbonyl group; (a13) a Z group; (a14) a (C1-C12) alkylsilyl group; (a15) a Z oxy group; (a17) a (C3-C6) cycloalkoxy group; (a21) a Z alkyl group; or (a37) a methoxy group, and R ２ (c1) a (C3-C6)alkyl group; (c2) a halo(C2-C6)alkyl group; (c3) a (C3-C6)cycloalkyl(C1-C6)alkyl group; (c6) a (C4-C6)alkenyl group; or (c7) a hydroxy(C3-C6)alkyl group, and R ３ (d1) a (C1-C6) alkyl group; or (d2) a halogen atom, or two R ３ are bonded to each other to form a group of the following formula R ３－２ may form a ring structure represented by X is an oxygen atom, Ar １ is a phenyl group or a pyrimidinyl group, and Ar ２ The compound or salt thereof according to claim 2, wherein is a pyridyl group.

4. An agricultural and horticultural fungicide comprising the compound or salt thereof according to claim 1 as an active ingredient.

5. An agricultural and horticultural fungicide comprising the compound or salt thereof according to claim 2 as an active ingredient.

6. An agricultural and horticultural fungicide comprising the compound or salt thereof according to claim 3 as an active ingredient.

7. An agricultural and horticultural plant disease control agent comprising the compound or salt thereof according to claim 1 as an active ingredient.

8. An agricultural and horticultural plant disease control agent comprising the compound or salt thereof according to claim 2 as an active ingredient.

9. An agricultural and horticultural plant disease control agent comprising the compound or salt thereof according to claim 3 as an active ingredient.

10. A method for controlling plant diseases, which comprises treating plants or soil with an effective amount of the agricultural and horticultural fungicide according to claim 4.

11. A method for controlling plant diseases, which comprises treating plants or soil with an effective amount of the agricultural and horticultural fungicide according to claim 5.

12. A method for controlling plant diseases, which comprises treating plants or soil with an effective amount of the agricultural and horticultural fungicide according to claim 6.

13. A method for controlling plant diseases, which comprises treating plants or soil with an effective amount of the agricultural and horticultural plant disease control agent according to claim 7.

14. A method for controlling plant diseases, which comprises treating plants or soil with an effective amount of the agricultural and horticultural plant disease control agent according to claim 8.

15. A method for controlling plant diseases, which comprises treating plants or soil with an effective amount of the agricultural and horticultural plant disease control agent according to claim 9.

16. Use of the compound or salt thereof according to claim 1 as a fungicide.

17. Use of the compound or salt thereof according to claim 2 as a fungicide.

18. Use of the compound or salt thereof according to claim 3 as a fungicide.

19. Use of the compound or salt thereof according to claim 1 as an agricultural or horticultural fungicide.

20. Use of the compound or salt thereof according to claim 2 as an agricultural or horticultural fungicide.

21. Use of the compound or salt thereof according to claim 3 as an agricultural or horticultural fungicide.

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