Oxirane amide compound or a salt thereof, and an agricultural / horticultural fungicide containing the same and a method using the same

Abstract

This invention provides a novel fungicide for agricultural and horticultural use. This invention relates to fungicides for agricultural and horticultural use containing compounds of the following general formula [I] or their salts, as active ingredients, and methods of application thereof (the symbols in the formula are as described in the specification).

Description

[Technical Field]

[0001] This invention relates to ethylene oxide amide compounds or their salts, and fungicides for agricultural and horticultural use containing such compounds as active ingredients, and methods of application thereof. [Previous Technology]

[0002] Patent Document 1 has reported a compound with anti-androgenic activity, describing an aniline compound having a certain epoxy group as an intermediate. Furthermore, Non-Patent Document 1 describes a method for synthesizing an alkylamide compound having a certain epoxy group. However, these documents do not describe the ethylene oxide amide compound of the present invention, nor do they disclose or imply any compound that can be used as a fungicide for agricultural and horticultural purposes. [Prior Art Documents] [Patent Documents]

[0003] [Patent Document 1] International Publication No. 2013 / 104831 (Non-Patent Document)

[0004] [Non-patent literature 1] Europe An Journal of OrgAnic Chemistry (2007), (11), 1730-1733 [Summary of the Invention]

[0005] [Problems to be Solved by the Invention] Losses caused by various diseases in crop production, such as agriculture and horticulture, remain substantial. Furthermore, due to factors such as resistance to existing pesticides, there is a need for the development of novel agro-horticultural fungicides. In recent years, from the perspective of saving labor or automating application, there is a need for fungicides with properties that can withstand various application methods, such as seed treatment, small-dose application, or local application. That is, fungicides for agro-horticulture should be stable in moderate heat and environments, and have moderate migration and diffusion within or near crops. On the other hand, considering the pursuit of sustainable agriculture and the impact of various toxicities or on surrounding organisms or the environment, there is a need for fungicides with various safety profiles, moderate residue levels, biodegradability, and environmental decomposition properties. [Means for Solving the Problems]

[0006] As a result of the inventors' dedicated research in order to solve the above-mentioned problems, they discovered that the ethylene oxide amide compound or its salts represented by general formula [I] have excellent control effects on agricultural and horticultural diseases. The inventors further repeated their research and found that the ethylene oxide amide compound or its salts represented by general formula [I] are suitable for various application methods and have excellent physical, chemical, and biological properties, thus completing this invention.

[0007] That is, the present invention relates to the following. [1] Compounds of general formula [I] or salts thereof: {wherein, R1 and R5 may be the same or different, each representing (a1) a halogen atom; (a2) a cyano group; (a3) ​​a nitro group; (a4) a hydroxyl group; (a5) an amino group; (a6) a (C1-C6) alkyl group; (a7) a (C2-C6) alkenyl group; (a8) a (C2-C6) alkynyl group; (a9) a (C3-C6) cycloalkyl group; (a10) a halo(C1-C6) alkyl group; (a11) a halo(C2-C6) alkenyl group; (a12) a halo(C2-C6) alkynyl group; (a13) a halo(C3-C6) cycloalkyl group; (a14) a (C1-C6) alkoxy group; (a15) a (C3-C6) cycloalkoxy group; (a16) a cycloalkoxy group; (a17) a cycloalkoxy group; (a18) a cycloalkoxy group; (a19) a cycloalkoxy group; (a10) a cycloalkoxy group; (a11) a cycloalkoxy group; (a12) a cycloalkynyl group; (a13) a cycloalkynyl group; (a14) a (C1-C6) alkoxy group; (a15) a (C3-C6) cycloalkoxy group; (a16) a cycloalkoxy group; (a17) a cycloalkoxy group; (a18) a cycloalkoxy group; (a19) a cycloalkoxy group; (a12) a cycloalkynyl group; (a13) a cycloalkynyl group; (a14) a cycloalkoxy group; (a15) (C1-C6)alkoxy(C1-C6)alkoxy; (a17) (C3-C6)cycloalkyl(C1-C6)alkoxy; (a18) halo(C1-C6)alkoxy; (a19) halo(C3-C6)cycloalkoxy; (a20) halo(C1-C6)alkoxy(C1-C6)alkoxy; (a21) halo(C3-C6)cycloalkyl(C1-C6)alkoxy; (a22) (C1-C6)alkylthio; (a23) (C1-C6)alkylsulfinyl; (a24) (C1-C6)alkylsulfinyl; (a25) halo(C1-C6)alkylthio; (a26) halo(C1-C6)alkylsulfinyl; (a27) halo(C1-C6)alkylsulfinyl; (a28) Phenyl; (a29) A substituted phenyl group having 1 to 5 substituents independently selected from substituent group Y on the ring; (a30) Phenoxy; (a31) A substituted phenoxy group having 1 to 5 substituents independently selected from substituent group Y on the ring; (a32) Phenyl (C1-C6)alkoxy; (a33) A substituted phenyl (C1-C6)alkoxy group having 1 to 5 substituents independently selected from substituent group Y on the ring; (a34) Pyridyl; (a35) A substituted pyridyl group having 1 to 4 substituents independently selected from substituent group Y on the ring; (a36) Pyridyloxy; (a37) A substituted pyridyloxy group having 1 to 4 substituents independently selected from substituent group Y on the ring; (a38) Thiophene; (a39) Substituted thiophene group having 1 to 3 substituents independently selected from substituent group Y on the ring; (a40) thiazolyl; (a41) substituted thiazolyl group having 1 or 2 substituents independently selected from substituent group Y on the ring; (a42) naphthyl; (a43) substituted naphthyl group having 1 to 7 substituents independently selected from substituent group Y on the ring; (a44) pyridazinyl;(a45) A substituted pyridazinyl group having 1 to 3 substituents independently selected from the substituent group Y on the ring; (a46) a pyrimidinyl group; or (a47) a substituted pyrimidinyl group having 1 to 3 substituents independently selected from the substituent group Y on the ring, or (a48) two adjacent R1 groups or two adjacent R5 groups combined to form a (C1-C6) alkylene group that can be substituted by 1 to 4 substituents independently selected from halogen atoms and (C1-C6) alkyl groups, wherein the substituent group Y is composed of (b1) halogen atoms; (b2) cyano; (b3) nitro; (b4) amino; (b5) (C1-C6) alkyl; (b6) (C2-C6) alkenyl; (b7) (C2-C6) ynyl; (b8) (C3-C6) cycloalkyl; (b9) (b10) Halo(C1-C6)alkyl; (b11) Halo(C2-C6)alkenyl; (b12) Halo(C3-C6)cycloalkyl; (b13) (C1-C6)alkoxy; (b14) (C1-C6)alkylthio; (b15) (C1-C6)alkylsulfinyl; (b16) (C1-C6)alkylsulfinyl; (b17) Halo(C1-C6)alkoxy; (b18) Halo(C1-C6)alkylthio; (b19) Halo(C1-C6)alkylsulfinyl; and (b20) Halo(C1-C6)alkylsulfinyl, where R2 and R3 may be the same or different, each representing a (c1) hydrogen atom; (c2) (C1-C6)alkyl; or (c3) halogen atom, or R2 and R3 bonded together, including the bonded carbon atoms, forming a 3- to 6-membered saturated aliphatic ring, R4 representing (d1) hydrogen atom; (d2) (C1-C6)alkyl; (d3) (C1-C6)alkoxy; (d4) (C2-C6)alkenyl; (d5) (C2-C6)alkynyl; (d6) (C3-C6)cycloalkyl; (d7) (C3-C6)cycloalkyl(C1-C6)alkyl; (d8) (C1-C6)alkoxy(C1-C6)alkyl; (d9) (C1-C6)alkylcarbonyl; or (d10) (C1-C6)alkoxycarbonyl, Ar1 and Ar2 may be the same or different, each representing (e1) phenyl; (e2) pyridinyl; (e3) N-oxide pyridinyl; (e4) Naphthyl; (e5) Thiopheneyl; (e6) Thiazolyl; (e7) Thiadiazolyl; (e8) Quinolinyl; (e9) Naphthidyl; (e10) Pyridazinyl; (e11) Pyrimidinyl; or (e12) Pyrazinyl, where X represents (f1) oxygen atom; or (f2) sulfur atom, m represents 0, 1, 2, 3, 4 or 5, and n represents 0, 1, 2, 3, 4 or 5.

[0008] [2] The compounds described above[1] or their salts R1 and R5 may be the same or different, each being (a1) a halogen atom; (a2) a cyano group; (a6) a (C1-C6) alkyl group; (a9) a (C3-C6) cycloalkyl group; (a10) a halo(C1-C6) alkyl group; (a14) a (C1-C6) alkoxy group; (a15) a (C3-C6) cycloalkoxy group; (a28) a phenyl group; (a29) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group Y on the ring; (a30) a phenoxy group; or (a31) a substituted phenoxy group having 1 to 5 substituents independently selected from the substituent group Y on the ring, or (a48-1) two adjacent R1 groups or two adjacent R5 groups combined to form a (C1-C6) alkyl group, wherein the substituent group Y is composed of the following (b1) Halogen atom; (b5) (C1-C6) alkyl; and (b13) (C1-C6) alkoxy, R2 and R3 may be the same or different, each being a (c1) hydrogen atom; or (c2) (C1-C6) alkyl, R4 being a (d1) hydrogen atom; or (d2) (C1-C6) alkyl, Ar1 and Ar2 may be the same or different, each being a (e1) phenyl; (e2) pyridinyl; (e3) N-oxypyridinyl; (e11) pyrimidinyl; or (e12) pyrazinyl, X being a (f1) oxygen atom, m being 0 or 1, and n being 0, 1, or 2.

[0009] [3] As described in [1] or [2] above, R1 and R5 may be the same or different, each being (a1) a halogen atom; (a2) a cyano group; (a6) a (C1-C6) alkyl group; (a9) a (C3-C6) cycloalkyl group; (a10) a halo(C1-C6) alkyl group; (a14) a (C1-C6) alkoxy group; (a15) a (C3-C6) cycloalkoxy group; (a28) a phenyl group; (a29) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group Y on the ring; (a30) a phenoxy group; or (a31) a substituted phenoxy group having 1 to 5 substituents independently selected from the substituent group Y on the ring, or (a48-1) two adjacent R1 groups or two adjacent R5 groups combined to form a (C1-C6) alkyl group. The substituent group Y is composed of the following: (b1) halogen atom; and (b5) (C1-C6) alkyl, R2 and R3 may be the same or different, each being a (c1) hydrogen atom; or (c2) (C1-C6) alkyl, R4 being a (d1) hydrogen atom; or (d2) (C1-C6) alkyl, Ar1 and Ar2 may be the same or different, each being a (e1) phenyl; (e2) pyridinyl; (e3) N-oxide pyridinyl; (e11) pyrimidinyl; or (e12) pyrazinyl, X being an (f1) oxygen atom, m being 0 or 1, and n being 0, 1, or 2.

[0010] [4] An agricultural and horticultural fungicide containing, as an active ingredient, any one of the compounds described in [1] to [3] above. [5] A method for controlling plant diseases, wherein plants or soil are treated with an effective amount of the agricultural and horticultural fungicide described in [4] above. [6] Use of a compound described in any one of [1] to [3] above as a fungicide.

[0011] [7] A compound of general formula [II-2] or a salt thereof: {wherein, R1 represents (a1-2) an iodine atom; (a2) a cyano group; (a6-1) a (C2-C6) alkyl group; (a9) a (C3-C6) cycloalkyl group; (a10-1) a halo(C1-C6) alkyl group (excluding trifluoromethyl); (a14-1) a (C2-C6) alkoxy group; (a15) a (C3-C6) cycloalkoxy group; (a28) a phenyl group; (a29) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group Y on the ring; (a30) a phenoxy group; or (a31) a substituted phenoxy group having 1 to 5 substituents independently selected from the substituent group Y on the ring, or (a48-1) two adjacent R1 groups combined to form a (C1-C6) alkyl group, The substituent group Y is composed of the following: (b1) halogen atom; (b5) (C1-C6) alkyl; and (b13) (C1-C6) alkoxy, R2 and R3 may be the same or different, each representing (c1) hydrogen atom; or (c2) (C1-C6) alkyl, Ar1 representing (e1) phenyl; (e2) pyridinyl; (e3) N-oxide pyridinyl; (e11) pyrimidinyl; or (e12) pyrazinyl, m representing 0 or 1.

[0012] [8] The compound or its salt R1 described above [7] is (a1-2) iodine atom; (a6-1) (C2-C6) alkyl; (a10-1) halo(C1-C6) alkyl (except for trifluoromethyl); (a14-1) (C2-C6) alkoxy; (a15) (C3-C6) cycloalkoxy; (a28) phenyl; (a29) substituted phenyl having 1 to 5 substituents independently selected from the substituent group Y on the ring; (a30) phenoxy; or (a31) substituted phenoxy having 1 to 5 substituents independently selected from the substituent group Y on the ring, the substituent group Y being composed of: (b1) halogen atom; (b5) (C1-C6) alkyl; and (b13) (C1-C6) alkoxy, R2 and R3 may be the same or different, each being a (c1) hydrogen atom; or a (c2) (C1-C6) alkyl group, Ar1 being an (e1) phenyl group, and m being 1. [Effects of the Invention]

[0013] The ethylene oxide amide compound or its salts of the present invention have excellent effects as fungicides for agricultural and horticultural use. In particular, they show high efficacy against black spot disease of Chinese cabbage, late blight of tomato, gray mold of cucumber, anthracnose of cucumber, rice blast, apple scab, powdery mildew of barley, leaf blight of wheat, sclerotinia stem rot, ring rot, late rot of grapes, acute wilt of soybean, red mold of wheat, sclerotinia stem rot of cruciferous vegetables, and leaf blight of rice and sesame.

Implementation Method

[0014] In the definition of the general formula [I] of the compound of the present invention, "halogen" means "halogen atom", usually representing chlorine atom, bromine atom, iodine atom or fluorine atom.

[0015] "(C1-C6)alkyl" refers to alkyl groups with 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, secondary butyl, tertiary butyl, n-pentyl, isopentyl, tertiary pentyl, neopentyl, tertiary pentyl, 2,3-dimethylpropyl, 1-ethylpropyl, 1-methylbutyl, 2-methylbutyl, n-hexyl, isohexyl, 2-hexyl, 3-hexyl, 2-methylpentyl, 3-methylpentyl, 1,1,2-trimethylpropyl, 3,3-dimethylbutyl, etc., in a straight-chain or branched-chain form.

[0016] "(C2-C6)alkenyl" refers to alkenyl groups with 2 to 6 carbon atoms, such as vinyl, allyl, isopropenyl, 1-butenyl, 2-butenyl, 2-methyl-2-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl, pentenyl, 1-hexenyl, 3,3-dimethyl-1-butenyl. "(C2-C6)ynyl" refers to ynyl groups with 2 to 6 carbon atoms, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 3-methyl-1-propynyl, 2-methyl-3-propynyl, pentenyl, 1-hexynyl, 3-methyl-1-butynyl, 3,3-dimethyl-1-butynyl.

[0017] "(C3-C6)cycloalkyl" refers to cyclic alkyl groups with 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. "(C1-C6)alkoxy" refers to alkoxy groups with 1 to 6 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, secondary butoxy, tertiary butoxy, n-pentyloxy, isopentyloxy, tertiary pentyloxy, neopentyloxy, 2,3-dimethylpropyloxy, 1-ethylpropyloxy, 1-methylbutyloxy, n-hexyloxy, isohexyloxy, and 1,1,2-trimethylpropyloxy. "(C3-C6)cycloalkoxy" refers to cyclic alkoxy groups with 3 to 6 carbon atoms, such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, and cyclohexyloxy.

[0018] "(C1-C6)alkylthio" refers to alkylthio groups with 1 to 6 carbon atoms, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, secondary butylthio, tertiary butylthio, n-pentylthio, isopentylthio, tertiary pentylthio, neopentylthio, 2,3-dimethylpropylthio, 1-ethylpropylthio, 1-methylbutylthio, n-hexylthio, isohexylthio, 1,1,2-trimethylpropylthio.

[0019] "(C1-C6)alkylsulfinyl" refers to alkylsulfinyl groups with 1 to 6 carbon atoms, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, secondary butylsulfinyl, tertiary butylsulfinyl, n-pentylsulfinyl, isopentylsulfinyl, tertiary pentylsulfinyl, neopentylsulfinyl, 2,3-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1-methylbutylsulfinyl, n-hexylsulfinyl, isohexylsulfinyl, and 1,1,2-trimethylpropylsulfinyl.

[0020] "(C1-C6)alkylsulfonyl" refers to alkylsulfonyl groups with 1 to 6 carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, secondary butylsulfonyl, tertiary butylsulfonyl, n-pentylsulfonyl, isopentylsulfonyl, tertiary pentylsulfonyl, neopentylsulfonyl, 2,3-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 1-methylbutylsulfonyl, n-hexylsulfonyl, isohexylsulfonyl, 1,1,2-trimethylpropylsulfonyl.

[0021] "(C1-C6)alkylcarbonyl" refers to an alkylcarbonyl group having 2 to 7 carbon atoms, such as acetyl, propionic, butyryl, 2-methylpropionic, pentapropyl, 2-methylbutyryl, 3-methylbutyryl, trimethylacetyl, hexyl, etc.

[0022] "(C1-C6)alkoxycarbonyl" refers to alkoxycarbonyl groups with 2 to 7 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, secondary butoxycarbonyl, tertiary butoxycarbonyl, pentyloxycarbonyl, etc.

[0023] The substituted positions of the above-mentioned "(C1-C6)alkyl", "(C2-C6)alkenyl", "(C2-C6)alkynyl", "(C3-C6)cycloalkyl", "(C1-C6)alkoxy", "(C3-C6)cycloalkoxy", "(C1-C6)alkylthio", "(C1-C6)alkylsulfinyl", "(C1-C6)alkylsulfonyl", "(C1-C6)alkylcarbonyl", "(C1-C6)alkoxycarbonyl" can be substituted by 1 or 2 or more halogen atoms. When there are 2 or more substituted halogen atoms, the halogen atoms can be the same or different.

[0024] When halogen atoms are substituted, they are respectively represented as "halogen(C1-C6)alkyl", "halogen(C2-C6)alkenyl", "halogen(C2-C6)alkynyl", "halogen(C3-C6)cycloalkyl", "halogen(C1-C6)alkoxy", "halogen(C3-C6)cycloalkoxy", "halogen(C1-C6)alkylthio", "halogen(C1-C6)alkylsulfinyl", "halogen(C1-C6)alkylsulfonyl", "halogen(C1-C6)alkylcarbonyl", "halogen(C1-C6)alkoxycarbonyl", etc.

[0025] “(C1-C6)alkylene” refers to alkylene groups with 1 to 6 carbon atoms, such as methylene, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tributyl, etc., which are straight-chain or branched chains.

[0026] In this invention, "(C1-C6)", "(C2-C6)", "(C3-C6)", etc., represent the range of carbon number of various substituents. Furthermore, the group to which the above substituents are attached can represent, as defined above, for example, "(C1-C6)alkoxy(C1-C6)alkyl" means that a straight-chain or branched alkoxy group with 1 to 6 carbon atoms is attached to a straight-chain or branched alkyl group with 1 to 6 carbon atoms.

[0027] R2 and R3 can combine with each other to form a 3 to 6-membered saturated aliphatic ring containing the carbon atoms they are bonded to. Examples of such "3 to 6-membered saturated aliphatic ring" include cyclopropane, cyclobutane, cyclopentane and cyclohexane.

[0028] The salts of the compounds represented by the general formula [I] of the present invention may include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate; organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, and p-toluenesulfonate; and inorganic or organic base salts such as sodium ion, potassium ion, calcium ion, and trimethylammonium ion.

[0029] The compounds and their salts represented by general formula [I] of the present invention may have one or more asymmetric centers in their structural formulas, and may also contain two or more optical isomers and non-mirror image isomers. The present invention also includes all kinds of optical isomers and mixtures thereof contained in any proportion. Furthermore, the compounds and their salts represented by general formula [I] of the present invention may also contain two or more geometric isomers derived from carbon-carbon double bonds in their structural formulas. The present invention also includes all kinds of geometric isomers and mixtures thereof contained in any proportion. Further, the compounds and their salts represented by general formula [I] of the present invention may also contain a plurality of tautomers. The present invention also includes all kinds of tautomers and mixtures thereof contained in any proportion.

[0030] Preferred forms of the compounds represented by general formula [I] of the present invention are disclosed below. The compounds represented by general formula [II-2] are used as synthetic intermediates for the compounds represented by general formula [I].

[0031] As R1, it is preferably (a1) a halogen atom, (a6) (C1-C6) alkyl, (a10) halo(C1-C6) alkyl, (a14) (C1-C6) alkoxy, (a15) (C3-C6) cycloalkoxy, (a28) phenyl, (a29) a substituted phenyl having 1 to 5 substituents independently selected from the self-substituent group Y on the ring, (a30) phenoxy, or (a31) a substituted phenoxy having 1 to 5 substituents independently selected from the self-substituent group Y on the ring. More preferably, it is a substituted phenoxy group having 1 to 5 substituents independently selected from each of the following groups: (a1) halogen atom, (a6) (C1-C6) alkyl, (a10) halo(C1-C6) alkyl, (a14) (C1-C6) alkoxy, (a15) (C3-C6) cycloalkoxy, (a28) phenyl, (a30) phenoxy, or (a31) ring having 1 to 5 substituents independently selected from each of the following groups: (a6) (C1-C6) alkyl, (a14) (C1-C6) alkoxy, (a15) (C3-C6) cycloalkoxy, (a28) phenyl, (a30) phenoxy, or (a31) ring having 1 to 5 substituents independently selected from each of the following groups: (a6) (C1-C6) alkyl, (a15) (C3-C6) cycloalkoxy, (a28) phenyl, or (a30) phenoxy. Even more preferably, it is (a6-2)(C3-C5)alkyl, (a15-1)(C5-C6)cycloalkoxy, (a28)phenyl or (a30)phenoxy, particularly preferably (a6-4)isopropyl, tributyl, tripentyl or neopentyl, (a15-2)cyclopentyloxy, (a28)phenyl or (a30)phenoxy.

[0032] As a substituent group Y, it is preferably composed of the following: (b1) halogen atom, (b5) (C1-C6) alkyl and (b13) (C1-C6) alkoxy, and more preferably composed of the following: (b1) halogen atom and (b5) (C1-C6) alkyl.

[0033] The R2 and R3 systems may be the same or different, each preferably being a (c1) hydrogen atom or a (c2)(C1-C6) alkyl atom, more preferably a (c2)(C1-C6) alkyl atom, even more preferably a (c2-1)(C1-C2) alkyl atom, and most preferably a (c2-2) methyl atom.

[0034] As R4, it is preferably a (d1) hydrogen atom or a (d2) (C1-C6) alkyl group, and more preferably a (d1) hydrogen atom.

[0035] As R5, it is preferably (a1) a halogen atom, (a2) a cyano group, (a6) (C1-C6) alkyl or (a9) (C3-C6) cycloalkyl, or (a48-1) two adjacent R5s combined to form a (C1-C6) alkylene group, more preferably (a1) a halogen atom or (a6) (C1-C6) alkyl, even more preferably (a1) a halogen atom or (a6-3) (C1-C2) alkyl, and particularly preferably (a1-1) a fluorine atom or a chlorine atom or (a6-5) a methyl group.

[0036] As Ar1, it is preferably (e1)phenyl or (e2)pyridyl, more preferably (e1)phenyl.

[0037] As Ar2, it is preferably (e2)pyridyl, (e3)N-oxidepyridyl, (e11)pyrimidinyl or (e12)pyrazinyl, more preferably (e2)pyridyl or (e3)N-oxidepyridyl, even more preferably (e2)pyridyl, and most preferably (e2-1)2-pyridyl.

[0038] As for X, it is preferably (f1) oxygen atom.

[0039] In particular, in the case where Ar1 is (e1)phenyl and X is an oxygen atom, Ar2 is preferably (e2)pyridyl or (e3)N-oxide pyridyl, more preferably (e2)pyridyl, and especially preferably (e2-1)2-pyridyl.

[0040] m and n can be the same or different, preferably 0, 1 or 2. As m, it is especially preferred to be 1.

[0041] As one state of the compound represented by general formula [I] of the present invention, when Ar1 is (e1)phenyl, Ar2 is (e2)pyridyl (preferably (e2-1)2-pyridyl), and X is an oxygen atom, the preferred compound system is R1 which is (a1)halogen atom, (a6) (C1-C6)alkyl, (a10)halo(C1-C6)alkyl, (a14) (C1-C6)alkoxy, (a15) (C3-C6)cycloalkoxy, (a28)phenyl, (a29) substituted phenyl with 1 to 5 substituents independently selected from the self-substituent group Y on the ring, (a30)phenoxy, or (a31) substituted phenoxy with 1 to 5 substituents independently selected from the self-substituent group Y on the ring. The substituent group Y is composed of the following: (b1) a halogen atom, (b5) a (C1-C6) alkyl group, and (b13) a (C1-C6) alkoxy group; R2 and R3 may be the same or different, each being a (c1) hydrogen atom or a (c2) (C1-C6) alkyl group; R4 is a (d1) hydrogen atom or a (d2) (C1-C6) alkyl group; R5 is a (a1) halogen atom, (a2) cyano group, (a6) a (C1-C6) alkyl group, or (a9) a (C3-C6) cycloalkyl group, or (a48-1) two adjacent R5 groups combined to form a (C1-C6) cycloalkyl group; m is 1, and n is 0, 1, or 2. More preferably, R1 is a (a1) halogen atom, (a6) (C1-C6) alkyl, (a10) halo(C1-C6) alkyl, (a14) (C1-C6) alkoxy, (a15) (C3-C6) cycloalkoxy, (a28) phenyl, (a29) substituted phenyl with 1 to 5 substituents independently selected from the self-substituent group Y, (a30) phenoxy, or (a31) substituted phenoxy with 1 to 5 substituents independently selected from the self-substituent group Y, wherein the substituent group Y is composed of: (b1) halogen atom and (b5) (C1-C6) alkyl, R2 and R3 may be the same or different, each being a (c1) hydrogen atom or (c2) (C1-C6) alkyl, and R4 is a (d1) hydrogen atom or (d2) (C1-C6) alkyl. R5 is (a1) a halogen atom, (a2) a cyano group, (a6) (C1-C6) an alkyl group or (a9) (C3-C6) a cycloalkyl group, or (a48-1) two adjacent R5 groups combined to form a (C1-C6) alkyl group, m is 1, and n is 0, 1 or 2.

[0042] As another form of the compound shown in general formula [I] of the present invention, when Ar1 is (e1)phenyl, Ar2 is (e2)pyridyl (preferably (e2-1)2-pyridyl), and X is an oxygen atom, the preferred compound system is R1 is (a6) (C1-C6)alkyl, (a14) (C1-C6)alkoxy, (a15) (C3-C6)cycloalkoxy, (a28)phenyl, (a30)phenoxy, or (a31) a substituted phenoxy group Y having 1 to 5 substituents independently selected on the ring, the substituted phenoxy group Y is composed of: (b1) halogen atom, (b5) (C1-C6)alkyl and (b13) (C1-C6)alkoxy, R2 and R3 may be the same or different, each being (c1) hydrogen atom or (c2) (C1-C6)alkyl, and R4 is (d1) hydrogen atom. R5 is a (a1) halogen atom or a (a6) (C1-C6) alkyl, m is 1, and n is 0, 1, or 2. More preferably, R1 is a (a6) (C1-C6) alkyl, (a28) phenyl, or (a30) phenoxy. R2 and R3 may be the same or different, each being a (c1) hydrogen atom or a (c2) (C1-C6) alkyl. R4 is a (d1) hydrogen atom. R5 is a (a1) halogen atom or a (a6) (C1-C6) alkyl, m is 1, and n is 0, 1, or 2.

[0043] As one example of the compound shown in general formula [I] of the present invention, Ar1 is (e1)phenyl, Ar2 is (e2)pyridyl (preferably (e2-1)2-pyridyl), and when X is an oxygen atom, more preferably R1 is (a6)(C1-C6)alkyl, (a15)(C3-C6)cycloalkoxy, (a28)phenyl or (a30)phenoxy, R2 and R3 may be the same or different, each being (c2)(C1-C6)alkyl, R4 is (d1) hydrogen atom, R5 is (a1) halogen atom or (a6)(C1-C6)alkyl, m is 1, and n is 0, 1 or 2, and even more preferably R1 is (a6-2)(C3-C5)alkyl, (a15-1)(C5-C6)cycloalkoxy, (a28)phenyl or (a30)phenoxy. R2 and R3 may be the same or different, each being a (c2-1)(C1-C2) alkyl group, R4 being a (d1) hydrogen atom, R5 being a (a1) halogen atom or a (a6-3)(C1-C2) alkyl group, m being 1, and n being 0, 1, or 2. In the preferred compound system, R1 is (a6-4) isopropyl, tributyl, tripentyl, or neopentyl, (a15-2) cyclopentyloxy, (a28) phenyl, or (a30) phenoxy, R2 and R3 are (c2-2) methyl, R4 is a (d1) hydrogen atom, R5 is a (a1-1) fluorine atom or chlorine atom or (a6-5) methyl, m being 1, and n being 0, 1, or 2.

[0044] Furthermore, as one example of the compound shown in the general formula [I] of the present invention, when Ar1 is (e1)phenyl, Ar2 is (e3)N-oxypyridyl, and X is an oxygen atom, the preferred compound system is R1 is (a6)(C1-C6)alkyl, (a28)phenyl or (a30)phenoxy, R2 and R3 may be the same or different, each being (c1) hydrogen atom or (c2)(C1-C6)alkyl, R4 is (d1) hydrogen atom, R5 is (a1) halogen atom or (a6)(C1-C6)alkyl, m is 1, and n is 0, 1 or 2. The more preferred compound system is R1 is (a6)(C1-C6)alkyl, R2 and R3 may be the same or different, each being (c2)(C1-C6)alkyl, R4 is (d1) hydrogen atom, R5 is (a6)(C1-C6)alkyl, m is 1, and n is 2.

[0045] Furthermore, as one embodiment of the compound represented by general formula [I] of the present invention, when Ar1 and Ar2 are (e2)pyridyl groups and X is an oxygen atom, the preferred compound system is that R1 is a (a1) halogen atom, (a6) (C1-C6) alkyl, (a10) halo(C1-C6) alkyl, (a28) phenyl or (a30) phenoxy, R2 and R3 may be the same or different, each being a (c1) hydrogen atom or (c2) (C1-C6) alkyl, R4 is a (d1) hydrogen atom, R5 is a (a1) halogen atom or (a6) (C1-C6) alkyl, m is 0 or 1, and n is 0, 1 or 2. A more preferred compound system is that R1 is a (a1) halogen atom, (a10) halo(C1-C6) alkyl or (a28) phenyl, R2 and R3 may be the same or different, each being a (c2) (C1-C6) alkyl. R4 is a (d1) hydrogen atom, R5 is a (a6)(C1-C6) alkyl group, m is 0 or 1, and n is 1 or 2.

[0046] Furthermore, as one example of the compound represented by general formula [I] of the present invention, when Ar1 is (e1)phenyl, Ar2 is (e2)pyridyl, and X is a sulfur atom, the preferred compound system is R1 is (a6)(C1-C6)alkyl, (a28)phenyl, or (a30)phenoxy, R2 and R3 may be the same or different, each being (c1) hydrogen atom or (c2)(C1-C6)alkyl, R4 is (d1) hydrogen atom, R5 is (a1) halogen atom or (a6)(C1-C6)alkyl, m is 1, and n is 0, 1, or 2. The more preferred compound system is R1 is (a6)(C1-C6)alkyl, R2 and R3 may be the same or different, each being (c2)(C1-C6)alkyl, R4 is (d1) hydrogen atom, R5 is (a6)(C1-C6)alkyl, and m and n are 1.

[0047] Furthermore, as one example of the compound shown in the general formula [I] of the present invention, when Ar1 is (e1)phenyl, Ar2 is (e3)N-oxypyridyl, and X is a sulfur atom, the preferred compound system is R1 is (a6)(C1-C6)alkyl, (a28)phenyl or (a30)phenoxy, R2 and R3 may be the same or different, each being (c1) hydrogen atom or (c2)(C1-C6)alkyl, R4 is (d1) hydrogen atom, R5 is (a1) halogen atom or (a6)(C1-C6)alkyl, m is 1, and n is 0, 1 or 2. The more preferred compound system is R1 is (a6)(C1-C6)alkyl, R2 and R3 may be the same or different, each being (c2)(C1-C6)alkyl, R4 is (d1) hydrogen atom, R5 is (a6)(C1-C6)alkyl, m is 1, and n is 2.

[0048] Furthermore, as one example of the compound represented by general formula [II-2] of the present invention, the preferred compound system R1 is (a1-2) iodine atom, (a2) cyano, (a6-1) (C2-C6) alkyl, (a9) (C3-C6) cycloalkyl, (a10-1) halo(C1-C6) alkyl (excluding trifluoromethyl), (a14-1) (C2-C6) alkoxy, (a15) (C3-C6) cycloalkoxy, (a28) phenyl, (a29) substituted phenyl having 1 to 5 substituents independently selected from the substituent group Y on the ring, (a30) phenoxy or (a31) substituted phenoxy having 1 to 5 substituents independently selected from the substituent group Y on the ring, or (a48-1) two adjacent R1s combined to form a (C1-C6) alkyl group. The substituent group Y is composed of the following: (b1) a halogen atom, (b5) a (C1-C6) alkyl group, and (b13) a (C1-C6) alkoxy group; R2 and R3 may be the same or different, each being a (c1) hydrogen atom or a (c2) a (C1-C6) alkyl group; Ar1 ​​is (e1) phenyl, (e2) pyridinyl, (e3) N-oxide pyridinyl, (e11) pyrimidinyl, or (e12) pyrazinyl; and m is 0 or 1. More preferably, R1 is (a1-2) an iodine atom, (a6-1) a (C2-C6) alkyl group, (a10-1) a halo(C1-C6) alkyl group (excluding trifluoromethyl), (a14-1) a (C2-C6) alkoxy group, (a15) a (C3-C6) cycloalkoxy group, (a28) a phenyl group, (a29) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group Y on the ring, (a30) a phenoxy group, or (a31) a substituted phenoxy group having 1 to 5 substituents independently selected from the substituent group Y on the ring, wherein the substituent group Y is composed of: (b1) a halogen atom, (b5) a (C1-C6) alkyl group, and (b13) a (C1-C6) alkoxy group. R2 and R3 may be the same or different, each being a (c1) hydrogen atom or a (c2) a (C1-C6) alkyl group. Ar1 is (e1)phenyl, and M is 1. In a more preferred compound system, Ar1 is (e1)phenyl, R1 is (a6-1)(C2-C6)alkyl, (a15)(C3-C6)cycloalkoxy, (a28)phenyl, or (a30)phenoxy, R2 and R3 may be the same or different, each being a (c1) hydrogen atom or a (c2)(C1-C6)alkyl atom, and m is 1. In an even more preferred compound system, Ar1 is (e1)phenyl, R1 is (a6-1)(C2-C6)alkyl, R2 and R3 may be the same or different, each being a (c2)(C1-C6)alkyl atom, and m is 1. In an even more preferred compound system, Ar1 is (e1)phenyl, R1 is (a6-2)(C3-C5)alkyl, R2 and R3 may be the same or different, each being a (c2-1)(C1-C2)alkyl atom, and m is 1.The optimal compound system has Ar1 as (e1)phenyl, R1 as (a6-4)isopropyl, tributyl, tripentyl, or neopentyl, R2 and R3 as (c2-2)methyl, and m as 1.

[0049] The compound represented by general formula [I] of the present invention or its salts can be manufactured, for example, by the manufacturing methods described below, but the present invention is not limited to such methods. Furthermore, the optical isomers of the compound represented by general formula [I] of the present invention can be manufactured by general optical analysis of racemic compounds (e.g., fractional crystallization of diastereomer salts derived from optically active bases or acids, or chromatography using chiral columns, etc.), or by asymmetric synthesis reactions known in general organic synthesis methods, or by reactions using suitable optically active compounds.

[0050] Manufacturing Method 1 The compound represented by general formula [I-1] of the present invention can be manufactured from the compound represented by general formula [II-1] by the following steps [a-1] and [a-2].

[0051] (The symbols in the formula are the same as those mentioned above.)

[0052] The compound of general formula [II-1] prepared in step [a-1] can be prepared by reacting it with an oxidizing agent in the presence of an inactive solvent to produce the compound of general formula [II-2]. Furthermore, optical isomers of the compound of general formula [II-2] can also be prepared, for example, by the methods described in J. Am. Chem. Soc. 1980, 102, 18, 5974–5976 or J. Am. Chem. Soc. 1996, 118, 40, 9806–9807, or by appropriate modifications thereof.

[0053] As an oxidizing agent that can be used in this reaction, examples include peroxides such as hydrogen peroxide, perbenzoic acid, m-chloroperbenzoic acid, and peracetic acid. The amount used can usually be appropriately selected from 1 mole to 5 moles relative to the compound shown in general formula [II-1].

[0054] Any inactive solvent that can be used in this reaction is that which does not significantly inhibit the reaction. Examples include chain or cyclic ethers such as diethyl ether, tetrahydrofuran (THF), and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; nitriles such as acetonitrile; esters such as ethyl acetate; organic acids such as formic acid and acetic acid; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinedione, and water. These inactive solvents can be used alone or in mixtures of two or more. The amount of inactive solvent used is not particularly limited as long as it is sufficient to dissolve the reaction reagents. It can usually be appropriately selected from 0.5 L to 100 L relative to 1 mole of the compound shown in general formula [II-1].

[0055] The reaction temperature of this reaction can generally be carried out in the range from -10°C to the boiling point of the solvent used. The reaction time varies depending on the scale of the reaction, the reaction temperature, etc., and although it is not fixed, it can usually be appropriately selected from a range of several minutes to 48 hours. After the reaction is completed, the target substance can be separated from the reaction system containing the target substance by conventional methods, and purified as needed by recrystallization, column chromatography, etc., to produce the target substance. Alternatively, it can be supplied separately to subsequent steps.

[0056] The manufacturing method of step [a-2] involves using the compounds of general formula [II-2] and general formula [III] in the presence of a base, a condensing agent, and an inactive solvent, via a condensation reaction to produce the compound of general formula [I-1] of the present invention. Furthermore, the compound of general formula [III] can also be produced using salts such as hydrochloride.

[0057] Condensing agents that can be used in this condensation reaction include, for example, acid activators such as phosgene, phosphorus trichloride, phosphorus oxychloride, oxalic acid, and thionyl chloride; carbodiimides such as N,N'-dicyclohexylcarbodiimide (DCC) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI); in addition, examples include phosphorus pentoxide, polyphosphoric acid, N,N'-carbonyldiimidazole, and 2-chloro-1-methylpyridine. Pyridium iodide (Xiangshan reagent), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride, bromotripyridinephosphonium hexafluorophosphate (BROP), O-(1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), N,N,N',N'-bis(tetramethylene)chloroureaium tetrafluoroborate, O-(1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), N,N,N',N'-bis(tetramethylene)chloroureaium tetrafluoroborate, O-(1H-benzotriazine-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), N,N,N',N'-bis(tetramethylene)chloroureaium tetrafluoroborate, O-(1H-benzotriazine-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), N,N,N',N'-bis(tetramethylene)chloroureaium tetrafluoroborate, O-(1H-benzotriazine-1-yloxy)tris(dimethylamino)chloroureaium tetrafluoroborate, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrafluorophosphate, bromotriaz ... O-(1H-benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylene)ureon hexafluorophosphate, O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethylureon tetrafluoroborate (TBTU), ...bis(tetramethylene)ureon hexafluorophosphate, O-(1H-benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylene)ureon tetrafluoroborate (TBTU), O-(1H-benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylene)ureon hexafluorophosphate Methylene ureonium tetrafluoroborate, O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethylureonium hexafluorophosphate (HATU), 1-hydroxybenzotriazole (HOBt), propylphosphonic anhydride (T3P), and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium salt (DMT-MM) can be used alone or in mixtures of two or more. The amount of condensing agent used is generally appropriately selected from 0.5 moles to 5 moles relative to the compound represented by general formula [II-2].

[0058] Examples of bases that can be used in this condensation reaction include carbonates such as lithium carbonate, lithium bicarbonate, sodium carbonate, sodium bicarbonate, potassium carbonate, cesium carbonate, potassium bicarbonate, calcium carbonate, and magnesium carbonate; acetates such as lithium acetate, sodium acetate, and potassium acetate; and organic bases such as pyridine, methylpyridine, dimethylpyridine, triethylamine, tributylamine, N,N-diisopropylethylamine, and 4-dimethylaminopyridine. The amount of base used is usually appropriately selected from 0.5 moles to 5 moles relative to the compound shown in general formula [II-2], and such bases can be used as solvents.

[0059] The inactive solvent that can be used in this condensation reaction is any solvent that does not significantly inhibit the reaction. Examples include chain or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane; chain or cyclic ethers such as diethyl ether, THF, and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; nitriles such as acetonitrile and isopropionitrile; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinedione. These inactive solvents can be used alone or in mixtures of two or more. The amount of inactive solvent used is only required to dissolve the reaction reagents and is not particularly limited. It can usually be appropriately selected from 0.5 L to 100 L relative to 1 mole of the compound shown in general formula [II-2]. Furthermore, when the aforementioned base is used as a solvent, no solvent may be used.

[0060] Since this condensation reaction is an isomolar reaction, each compound can be used in equal molar amounts, or any compound can be used in excess. The reaction temperature of this condensation reaction can usually be carried out in the range from 0°C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., and although it is not fixed, it can usually be appropriately selected in the range of several minutes to 48 hours. After the reaction is completed, the target compound can be isolated from the reaction vessel containing the target compound by conventional methods. If necessary, it can be purified by recrystallization, column chromatography, etc., thereby producing the target compound.

[0061] Manufacturing Method 2 The compound represented by general formula [I-2] of the present invention can be manufactured from the compound represented by general formula [II-1] via the following steps [b-1] and [b-2]. Furthermore, the reaction conditions of step [b-1] are the same as those of step [a-2] above, and the reaction conditions of step [b-2] are the same as those of step [a-1] above.

[0062] (The symbols in the formula are the same as those mentioned above.)

[0063] Manufacturing Method 3 The compound represented by general formula [I-3] of the present invention can be manufactured from the compound represented by general formula [II-4] via the following steps [c-1] and [c-2]. Furthermore, the reaction conditions in step [c-1] are the same as those in step [a-2] above.

[0064] (In the formula, Ar1, Ar2, R1, R4, R5, m and n are the same as those mentioned above, W- represents halide ions, tetrafluoroborate ions or hexafluorophosphate ions, and p is 0 or 1.)

[0065] The manufacturing method in step [c-2] is based on the Corey-Chaykovsky reaction, i.e., the method described in Org. Synth. 1969, 49, 78. The compounds shown in general formula [II-5] and general formula [IV] can be reacted in the presence of a base and an inactive solvent to produce the compound shown in general formula [I-3] of the present invention.

[0066] Examples of compounds represented by general formula [IV] include trimethyl sulfonium iodide, trimethyl sulfonium bromide, trimethyl thionium tetrafluoroborate, trimethyl thionium hexafluorophosphate, etc., and the amount used is usually appropriately selected in the range of 1 mole to 10 moles relative to the compounds represented by general formula [II-5].

[0067] Examples of bases that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, and potassium bicarbonate; acetates such as sodium acetate and potassium acetate; alkali metal alkoxides such as potassium butoxy, sodium methoxy, and sodium ethoxy; tertiary amines such as triethylamine, N,N-diisopropylethylamine, and diazabicycloundecene; and nitrogen-containing aromatic compounds such as pyridine and N,N-dimethyl-4-aminopyridine. The amount used is usually appropriately selected in the range of 1 to 10 moles relative to the compound shown in general formula [II-5].

[0068] Any inactive solvent that can be used in this reaction is acceptable as long as it does not significantly inhibit the reaction. Examples include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; nitriles such as acetonitrile and isopropyl nitrile; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinedione. These inactive solvents can be used alone or in mixtures of two or more. The amount of inactive solvent used is not particularly limited as long as it is sufficient to dissolve the reaction reagents. Generally, it can be appropriately selected from 0.5 L to 100 L relative to 1 mole of the compound shown in general formula [II-5].

[0069] The reaction temperature of this reaction can generally be carried out in the range from -10°C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale and reaction temperature, and although it is not fixed, it can generally be appropriately selected from a range of several minutes to 48 hours. Furthermore, this reaction can also be carried out in an environment of inert gases such as nitrogen or argon. After the reaction is completed, the target substance can be isolated from the reaction system containing the target substance using conventional methods, and purified as needed by recrystallization, column chromatography, etc., to produce the target substance.

[0070] Manufacturing Method 4 The compound represented by general formula [I-4] of the present invention can be manufactured from the compound represented by general formula [II-3'] via the following steps [d-1] and [d-2]. Furthermore, the reaction conditions in step [d-2] are the same as those in step [a-1] above.

[0071] (The symbols in the formula are the same as those mentioned above.)

[0072] The compound of general formula [II-3'] in step [d-1] can be produced by reacting with a vulcanizing agent in the presence of an inactive solvent to produce the compound of general formula [II-6].

[0073] As a sulfiding agent that can be used in this reaction, examples include Lawesson's Reagent, phosphorus pentasulfide, etc., and the amount used is usually appropriately selected in the range of 1.0 moles to 10 moles relative to the compound shown in general formula [II-3'].

[0074] This reaction may or may not use a solvent. Any inactive solvent that can be used in this reaction is acceptable as long as it does not significantly inhibit the reaction. Examples include chain or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; chain or cyclic ethers such as diethyl ether, methyl tributyl ether, dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; nonprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinedione; and alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol. These inactive solvents may be used alone or in mixtures of two or more. The amount used is usually appropriately selected in the range of 0.1 to 100 L relative to 1 mole of the compound shown in general formula [II-3'].

[0075] The reaction temperature of this reaction can generally be carried out in the range from about 0°C to the boiling point of the inactive solvent used. The reaction time varies depending on the scale of the reaction and the reaction temperature, and although it is not fixed, it can generally be appropriately selected in the range of several minutes to 48 hours. After the reaction is completed, the target substance can be isolated from the reaction system containing the target substance by conventional methods, and purified as needed by recrystallization, column chromatography, etc. to produce the target substance.

[0076] Manufacturing Method 5 The compound represented by general formula [I-1'] of the present invention can be manufactured from the compound represented by general formula [II-7] via the following steps [e-1], [e-2] and [e-3]. Furthermore, the reaction conditions of step [e-3] are the same as those of the aforementioned step [a-2].

[0077] (In the formula, Ar1, Ar2, R1, R2, R3, R4, R5, m, and n are the same as described above. Carbon marked with * indicates asymmetric carbon.)

[0078] The compound of general formula [II-7] in step [e-1] can be stereoselectively produced by reacting with D-(-) or L-(+)-tartrate and hydrogen peroxide in the presence of a metal catalyst and an inactive solvent.

[0079] As a metal catalyst that can be used in this reaction, examples include titanium(IV) ethoxide, titanium(IV) isopropoxide, titanium(IV) tributoxide, vanadium(V) oxytriisopropoxide, etc., and the amount used is usually appropriately selected in the range of 0.01 moles to 10 moles relative to the compound shown in general formula [II-7].

[0080] As tartrate esters that can be used in this reaction, examples include D-(-)-dimethyl tartrate, L-(+)-dimethyl tartrate, D-(-)-diethyl tartrate, L-(+)-diethyl tartrate, D-(-)-diisopropyl tartrate, L-(+)-diisopropyl tartrate, etc., and the amount used is usually appropriately selected in the range of 0.5 moles to 5 moles relative to the metal catalyst.

[0081] As for hydrogen peroxide that can be used in this reaction, examples include tert-butyl hydrogen peroxide, cumene hydrogen peroxide, etc., and the amount used is usually appropriately selected in the range of 1 mole to 10 moles relative to the compound shown in general formula [II-7].

[0082] Any inactive solvent that can be used in this reaction is that which does not significantly inhibit the reaction. Examples include chain or cyclic ethers such as diethyl ether, tetrahydrofuran (THF), and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; nitriles such as acetonitrile; esters such as ethyl acetate; organic acids such as formic acid and acetic acid; polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinedione, and water. These inactive solvents can be used alone or in mixtures of two or more. The amount of inactive solvent used is not particularly limited as long as it is sufficient to dissolve the reaction reagents. Generally, it can be appropriately selected from 0.5 L to 100 L relative to 1 mole of the compound shown in general formula [II-7].

[0083] The reaction temperature of this reaction can generally be carried out in the range from -40°C to the boiling point of the solvent used. The reaction time varies depending on the scale of the reaction, the reaction temperature, etc., and although it is not fixed, it can usually be appropriately selected in the range of several minutes to 72 hours. After the reaction is completed, the target substance can be isolated from the reaction system containing the target substance by conventional methods, and purified as needed by recrystallization, column chromatography, etc., to produce the target substance. Alternatively, it can be directly supplied to subsequent steps without isolation.

[0084] The compound of general formula [II-8] in step [e-2] can be produced by reaction with an oxidant in the presence of an inactive solvent, with or without a metal catalyst.

[0085] As an oxidizing agent that can be used in this reaction, examples include sodium periodate, potassium permanganate, chromium trioxide, hydrogen peroxide, N-methylmorpholine N-oxide, Oxone (registered trademark), etc., and the amount used is usually appropriately selected in the range of 1 mole to 10 moles relative to the compound shown in general formula [II-8].

[0086] As a metal catalyst that can be used in this reaction, examples include ruthenium(III) chloride and its hydrate, ruthenium dioxide, vanadium pentoxide, sodium tungstate, etc., and the amount used is usually appropriately selected in the range of 0.001 moles to 0.5 moles relative to the compound shown in general formula [II-8].

[0087] Any inactive solvent that can be used in this reaction is acceptable as long as it does not significantly inhibit the reaction. Examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; nitriles such as acetonitrile; esters such as ethyl acetate; organic acids such as formic acid and acetic acid; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinedione, and water. These inactive solvents can be used alone or in mixtures of two or more. The amount of inactive solvent used is not particularly limited as long as it is sufficient to dissolve the reaction reagents. Generally, it can be appropriately selected from 0.5 L to 100 L relative to 1 mole of the compound shown in general formula [II-8].

[0088] The reaction temperature of this reaction can generally be carried out in the range from -10°C to the boiling point of the solvent used. The reaction time varies depending on the scale of the reaction, the reaction temperature, etc., and although it is not fixed, it can usually be appropriately selected from a range of several minutes to 48 hours. After the reaction is completed, the target substance can be isolated from the reaction system containing the target substance by conventional methods, and purified as needed by recrystallization, column chromatography, etc., to produce the target substance. Alternatively, it can be directly supplied to subsequent steps without isolation.

[0089] Manufacturing Method 6 The compound represented by general formula [I-1''] of the present invention can be manufactured from the compound represented by general formula [II-9] via the following steps [f-1] and [f-2].

[0090] (In the formula, Ar1, Ar2, R1, R2, R3, R5, m, and n are the same as described above. L refers to a detached radical, such as chlorine, bromine, iodine, (C1-C6)alkylcarbonyloxy, (C1-C6)alkoxycarbonyloxy, etc.)

[0091] The compound of general formula [II-9] in step [f-1] can be produced by reacting with hydrogen peroxide in the presence or absence of an inactive solvent and a base, to produce the compound of general formula [II-10].

[0092] As bases that can be used in this reaction, examples include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, and potassium bicarbonate; acetates such as sodium acetate and potassium acetate; alkali metal alkoxides such as potassium tert-butoxy, sodium methoxy, and sodium ethoxy; tertiary amines such as triethylamine, N,N-diisopropylethylamine, and diazabicycloundecene; and nitrogen-containing aromatic compounds such as pyridine and N,N-dimethyl-4-aminopyridine. The amount used is usually appropriately selected in the range of 1 to 10 moles relative to the compound shown in general formula [II-9].

[0093] The amount of hydrogen peroxide used relative to the compound represented by general formula [II-9] can generally be appropriately selected in the range of 1 mole to 10 moles.

[0094] Any inactive solvent that can be used in this reaction may be used as long as it does not significantly inhibit the reaction. Examples include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; nitriles such as acetonitrile and isopropyl nitrile; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinedione, and water. These inactive solvents may be used alone or in mixtures of two or more. The amount of inactive solvent used is not particularly limited as long as it is sufficient to dissolve the reaction reagents. Generally, it can be appropriately selected from 0.5 L to 100 L relative to 1 mole of the compound shown in general formula [II-9].

[0095] The reaction temperature of this reaction can generally be carried out in the range from -10°C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale and reaction temperature, and although it is not fixed, it can generally be appropriately selected from a range of several minutes to 48 hours. Furthermore, this reaction can be carried out in an environment of inert gas such as nitrogen or argon. After the reaction is completed, the target substance can be isolated from the reaction system containing the target substance by conventional methods, and purified as needed by recrystallization, column chromatography, etc., to produce the target substance. Alternatively, it can be directly supplied to subsequent steps without isolation.

[0096] The manufacturing method of step [f-2] involves reacting the compounds of general formula [II-10] and general formula [III'] in the presence or absence of an inactive solvent and a base to produce the compound of general formula [I-1'']. Furthermore, the compound of general formula [III'] can also be produced using salts such as hydrochloride.

[0097] As a base that can be used in this reaction, examples include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, and potassium bicarbonate; acetates such as sodium acetate and potassium acetate; alkali metal alkoxides such as potassium tert-butoxy, sodium methoxy, and sodium ethoxy; tert-amines such as triethylamine, N,N-diisopropylethylamine, and diazabicycloundecene; and nitrogen-containing aromatic compounds such as pyridine and N,N-dimethyl-4-aminopyridine. The amount used is usually appropriately selected in the range of 1 to 10 moles relative to the compound shown in general formula [II-10].

[0098] Any inactive solvent that can be used in this invention is acceptable as long as it does not significantly inhibit the reaction. Examples include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; nitriles such as acetonitrile and isopropyl nitrile; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinedione, and water. These inactive solvents can be used alone or in mixtures of two or more. The amount of inactive solvent used is not particularly limited as long as it is sufficient to dissolve the reaction reagents, and is generally suitable in the range of 0.5 L to 100 L relative to 1 mole of the compound shown in general formula [II-10].

[0099] Since this reaction is an isomolar reaction, each compound can be used in equal molar amounts, or any compound can be used in excess. The reaction temperature can generally be carried out in the range from -10°C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale and reaction temperature, and although it is not fixed, it can generally be appropriately selected from a range of several minutes to 48 hours. Furthermore, this reaction can also be carried out in an inert gas environment such as nitrogen or argon. After the reaction is completed, the target compound can be isolated from the reaction system containing the target compound using conventional methods, and purified as needed by recrystallization, column chromatography, etc., to produce the target compound.

[0100] Method 1 for manufacturing starting material The compound represented by general formula [II-1] of methods 1 and 2 may be manufactured, for example, by the method described in Org. Lett. 2013, 15, 14, 3722-3725 or by appropriate modifications thereof.

[0101] Method 2 for manufacturing starting material The compound of general formula [II-4] of method 3 can be manufactured, for example, by the method described in J. Am. Chem. Soc. 2019, 141, 41, 16237-16242 or by appropriate modifications thereof.

[0102] The compound of general formula [II-3'] of manufacturing method 4 can be manufactured from the compound of general formula [II-1] and the compound of general formula [III] according to the reaction of step [a-2] of manufacturing method 1.

[0103] Method 4 for manufacturing starting material The compound of general formula [II-7] of manufacturing method 5 can be manufactured from the compound of general formula [II-11] via the following steps [g-1].

[0104] {In the formula, Ar1, R1, R2, R3, and m are the same as described above. M represents B(OH)2 group, B(OR6)2 group (in the formula, R6 can be the same or different, representing (C1-C10) alkyl, or two R6s combined to form -CH2CH2- group or -C(CH3)2C(CH3)2- group) or Sn(R7)3 group (in the formula, R7 can be the same or different, representing (C1-C10) alkyl). Z refers to halogen atoms such as chlorine, bromine, and iodine.}

[0105] The compound shown in general formula [II-11] and the compound shown in general formula [V] can be produced by cross-coupling reaction in the presence of palladium catalyst, base and inactive solvent, via a compound shown in general formula [II-7].

[0106] Examples of palladium catalysts that can be used in this reaction include, for example, metal salts such as palladium chloride, palladium bromide, palladium iodide, and palladium acetate; π-allyl palladium chloride dimer; palladium acetopyruvate; dichlorobis(acetonitrile) palladium; dichlorobis(benzonitrile) palladium; bis(dibenzylacetone) palladium; tri(dibenzylacetone) dipapadium; tri(dibenzylacetone) dipapadium (chloroform adduct); dichlorodiamine palladium; dichlorobis(triphenylphosphine) palladium; dichlorobis(tricyclohexylphosphine) palladium; and tetra(triphenylphosphine). Palladium, dichloro[1,2-bis(diphenylphosphino)ethane]palladium, dichloro[1,3-bis(diphenylphosphino)propane]palladium, dichloro[1,4-bis(diphenylphosphino)butane]palladium, dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium, diphenylphosphinoferrocene dichloropalladium-dichloromethane complex, and other complexes, the amount of such metal catalyst used relative to the compound represented by general formula [II-11] can generally be appropriately selected in the range of 0.001 moles to 0.5 moles.

[0107] These palladium catalysts can be used alone or in combination with tertiary phosphine. Examples of tertiary phosphines that can be used in this reaction include, for example, triphenylphosphine, trimethylphosphine, triethylphosphine, tributylphosphine, tris(tertiary butyl)phosphine, tricyclohexylphosphine, trio-o-tolylphosphine, trioctylphosphine, 9,9-dimethyl-4,5-bis(diphenylphosphine)oxanthracene (Xantphos), 2-(di-tertiary butylphosphine)biphenyl, 2-(dicyclohexylphosphine)biphenyl, and 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (SP). 1,2-bis(diphenylphosphine)ethane, 1,3-bis(diphenylphosphine)propane, 1,4-bis(diphenylphosphine)butane, 1,1'-bis(diphenylphosphine)ferrocene, (R)-(+)-2,2'-bis(diphenylphosphine)-1,1'-binaphthyl, (S)-(-)-2,2'-bis(diphenylphosphine)-1,1'-binaphthyl, (±)-2,2'-bis(diphenylphosphine)-1,1'-binaphthyl, etc. The amount of these tertiary phosphines used relative to the palladium catalyst can typically be appropriately selected in the range of 0.5 moles to 10 moles.

[0108] As a base that can be used in this reaction, examples include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, and tripotassium phosphate, as well as alkali metal alkoxides such as potassium tert-butoxy, sodium methoxy, and sodium ethoxy. The amount used is usually appropriately selected in the range of 1 to 10 moles relative to the compound shown in general formula [II-11].

[0109] Any inactive solvent that can be used in this reaction is that which does not significantly inhibit the reaction. Examples include alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol; chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; nitriles such as acetonitrile and isopropyl nitrile; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinedione, and water. These inactive solvents can be used alone or in mixtures of two or more. The amount of inactive solvent used is not particularly limited as long as it is sufficient to dissolve the reaction reagents. Generally, it can be appropriately selected from 0.5 L to 100 L relative to 1 mole of the compound shown in general formula [II-11].

[0110] Since this reaction is an isomolar reaction, any compound can be used in equal molar amounts, or any compound can be used in excess. The reaction temperature can generally be carried out in the range from room temperature to the boiling point of the solvent used. The reaction time varies depending on the reaction scale and reaction temperature, and although it is not fixed, it can generally be appropriately selected from a range of several minutes to 48 hours. Furthermore, this reaction can also be carried out in an inert gas environment such as nitrogen or argon. After the reaction is completed, the target compound can be isolated from the reaction system containing the target compound using conventional methods, and purified as needed by recrystallization, column chromatography, etc., to produce the target compound. Alternatively, it can be directly supplied to subsequent reactions without isolation.

[0111] Method 5 for manufacturing starting material The compound of general formula [II-9] of method 6 can be manufactured from the compound of general formula [II-12] by the following steps [h-1] and [h-2].

[0112] (The symbols in the formula are the same as those mentioned above.)

[0113] The manufacturing method of step [h-1] involves reacting the compound of general formula [II-12] and the compound of general formula [VI] in the presence of Lewis acid and an inactive solvent to produce the compound of general formula [II-13].

[0114] As a zeolite that can be used in this reaction, examples include ferric chloride, aluminum chloride, tin chloride, zinc chloride, etc., and the amount used is usually appropriately selected in the range of 1 mole to 10 moles relative to the compound shown in general formula [II-12].

[0115] Any inactive solvent that can be used in this reaction is that which does not significantly inhibit the reaction. Examples include alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol; chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; nitriles such as acetonitrile and isopropyl nitrile; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinedione, and water. These inactive solvents can be used alone or in mixtures of two or more. The amount of inactive solvent used is not particularly limited as long as it is sufficient to dissolve the reaction reagents. Generally, it can be appropriately selected from 0.5 L to 100 L relative to 1 mole of the compound shown in general formula [II-12].

[0116] Since this reaction is an isomolar reaction, each compound can be used in equal molar amounts, or any compound can be used in excess. The reaction temperature can generally be carried out in the range from -10°C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale and reaction temperature, and although it is not fixed, it can generally be appropriately selected from a range of several minutes to 48 hours. Furthermore, this reaction can also be carried out in an inert gas environment such as nitrogen or argon. After the reaction is completed, the target compound can be isolated from the reaction system containing the target compound using conventional methods, and purified as needed by recrystallization, column chromatography, etc., to produce the target compound. Alternatively, it can be directly supplied to subsequent reactions without isolation.

[0117] The compound of general formula [II-13] can be produced by reacting with a cyaniding agent in the presence of an inactive solvent, with or without an interphase transfer catalyst, according to the manufacturing method of step [h-2].

[0118] As a cyaniding agent that can be used in this reaction, examples include sodium cyanide, potassium cyanide, trimethylsilyl cyanide, etc., and the amount used is usually appropriately selected in the range of 1 mole to 10 moles relative to the compound shown in general formula [II-13].

[0119] As a phase transfer catalyst that can be used in this reaction, examples include quaternary ammonium salts such as tetrabutylammonium hydrogen sulfate and tetrabutylammonium bromide, phosphonium salts such as tetrabutylphosphonium bromide, crown ethers such as 18-crown-6, etc., and the amount used is usually appropriately selected in the range of 0.001 moles to 0.5 moles relative to the compound shown in general formula [II-13].

[0120] Any inactive solvent that can be used in this invention is acceptable as long as it does not significantly inhibit the reaction. Examples include alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol; chain or cyclic ethers such as diethyl ether, tetrahydrofuran (THF), and dioxane; acids such as acetic acid and propionic acid; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidineone, and water. These inactive solvents can be used alone or in mixtures of two or more. The amount of inactive solvent used is not particularly limited as long as it is sufficient to dissolve the reaction reagents, and is generally suitable in the range of 0.5 L to 100 L relative to 1 mole of the compound shown in general formula [II-13].

[0121] The reaction temperature of this reaction can generally be carried out in the range from -10°C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale and reaction temperature, and although it is not fixed, it can usually be appropriately selected from a range of several minutes to 48 hours. After the reaction is completed, the target substance can be isolated from the reaction system containing the target substance using conventional methods, and purified as needed by recrystallization, column chromatography, etc., to produce the target substance. Alternatively, it can be directly supplied to subsequent reactions without isolation.

[0122] Optical isomers of the compounds shown in general formulas [I], [II-2], [II-2'], and [II-8] can be manufactured by selecting appropriate starting material compounds. Furthermore, the isomers can be separated by utilizing the differences in their physicochemical properties.

[0123] The following are representative examples of compounds represented by general formula [I] of the present invention, as shown in Tables 1 to 4, but the present invention is not limited to such examples. In the following tables, Me represents methyl, Et represents ethyl, i-Pr represents isopropyl, t-Bu represents tributyl, t-Amyl represents tripentyl, c-Pr represents cyclopropyl, c-Pen represents cyclopentyl, and Ph represents phenyl. The numbers indicating the substitution positions of substituents (R1)m and (R5)n correspond to the positions of the numbers described in the structural formulas shown in the following general formulas [IA], [IB], [IC], [ID], and [II-2-E]. The physical property values ​​indicate melting point (°C), refractive index (nd), or 1H-NMR. Furthermore, in the tables, the inclusion of A or b in the compound number column (e.g., A-14a, A-14b) indicates that the compound is an optical isomer. The parentheses in the refractive index indicate the measurement temperature (°C). The 1H-NMR data are shown in Table 6.

[0124]

[0125] [Table 1-1] Table 1 Compound numbering (R 1 ) m R 2 R 3 R 4 Q Physical property value A-1 4-t-Bu Me Me H 5,6-diMe-pyridin-2-yl 94-96 A-2 4-t-Bu H H H 5,6-diMe-pyridin-2-yl NMR A-3 4-t-Bu Me Me H NMR A-4 4-t-Bu Me Me H Pyridin-2-yl NMR A-4a 4-t-Bu Me Me H Pyridin-2-yl A-4b 4-t-Bu Me Me H Pyridin-2-yl A-5 4-PhO Me Me H Pyridin-2-yl NMR A-6 4-PhO Me Me H 5,6-diMe-pyridin-2-yl NMR A-6a 4-PhO Me Me H 5,6-diMe-pyridin-2-yl A-6b 4-PhO Me Me H 5,6-diMe-pyridin-2-yl A-7 4-PhO Me Me H 5-Me-pyridin-2-yl NMR A-8 4-PhO Me Me H 5-F-pyridin-2-yl NMR A-9 4-Ph Me Me H 5-Cl-pyridin-2-yl 128-130 A-10 4-i-Pr Me Me H Pyridin-2-yl NMR A-11 4-i-Pr Me Me H 5-Me-pyridin-2-yl NMR A-11a 4-i-Pr Me Me H 5-Me-pyridin-2-yl A-11b 4-i-Pr Me Me H 5-Me-pyridin-2-yl A-12 4-i-Pr Me Me H 5-F-pyridin-2-yl NMR A-13 4-i-Pr Me Me H 5-Cl-pyridin-2-yl 98-100 A-14 4-t-Bu Me Me H 5-Me-pyridin-2-yl 84-86 A-14a 4-t-Bu Me Me H 5-Me-pyridin-2-yl 121-123 A-14b 4-t-Bu Me Me H 5-Me-pyridin-2-yl 121-123 A-15 4-t-Bu Me Me H 6-Me-pyridin-2-yl NMR A-15a 4-t-Bu Me Me H 6-Me-pyridin-2-yl A-15b 4-t-Bu Me Me H 6-Me-pyridin-2-yl A-16 4-t-Bu Me Me H 5-Cl-pyridin-2-yl 140-142 A-17 4-t-Amyl Me Me H Pyridin-2-yl NMR A-18 4-t-Amyl Me Me H 5-Me-pyridin-2-yl NMR A-19 4-t-Amyl Me Me H 5,6-diMe-pyridin-2-yl NMR A-19a 4-t-Amyl Me Me H 5,6-diMe-pyridin-2-yl A-19b 4-t-Amyl Me Me H 5,6-diMe-pyridin-2-yl A-20 4-t-Amyl Me Me H 5-F-pyridin-2-yl 116-118 (In the table, * indicates the junction.)

[0126] [Table 1-2] Table 1 (Continued) Compound number (R 1 ) m R 2 R 3 R 4 Q Physical property value A-21 4-i-Pr Me Me H 5,6-diMe-pyridin-2-yl NMR A-21a 4-i-Pr Me Me H 5,6-diMe-pyridin-2-yl A-21b 4-i-Pr Me Me H 5,6-diMe-pyridin-2-yl A-22 4-Ph Me Me H Pyridin-2-yl 101-103 A-23 4-Ph Me Me H 5,6-diMe-pyridin-2-yl 92-94 A-24 4-Ph Me Me H 5-Me-pyridin-2-yl 120-122 A-25 4-Ph Me Me H 5-F-pyridin-2-yl 96-98 A-25a 4-Ph Me Me H 5-F-pyridin-2-yl A-25b 4-Ph Me Me H 5-F-pyridin-2-yl A-26 4-t-Bu Me Me H 5-F-pyridin-2-yl 117-119 A-27 4-PhO Me Me H 5-Cl-pyridin-2-yl NMR A-27a 4-PhO Me Me H 5-Cl-pyridin-2-yl A-27b 4-PhO Me Me H 5-Cl-pyridin-2-yl A-28 4-(2-Me-PhO) Me Me H 5,6-diMe-pyridin-2-yl A-29 4-(2-Me-PhO) Me Me H 5-Me-pyridin-2-yl A-30 4-(2-Me-PhO) Me Me H 5-F-pyridin-2-yl A-31 4-(2-F-PhO) Me Me H 5,6-diMe-pyridin-2-yl A-32 4-(2-F-PhO) Me Me H 5-Me-pyridin-2-yl A-33 4-(2-F-PhO) Me Me H 5-F-pyridin-2-yl A-34 4-(2-OMe-PhO) Me Me H 5,6-diMe-pyridin-2-yl A-35 4-(2-OMe-PhO) Me Me H 5-Me-pyridin-2-yl A-36 4-(2-OMe-PhO) Me Me H 5-F-pyridin-2-yl A-37 4-(i-PrO) Me Me H 5,6-diMe-pyridin-2-yl 1.5390 (24.7) A-38 4-(i-PrO) Me Me H 5-Me-pyridin-2-yl 1.4569 (24.8) A-39 4-(i-PrO) Me Me H 5-F-pyridin-2-yl 1.5272 (24.6) A-40 4-(c-PenO) Me Me H 5,6-diMe-pyridin-2-yl NMR A-41 4-(c-PenO) Me Me H 5-Me-pyridin-2-yl 1.5431 (26.9) A-42 4-(c-PenO) Me Me H 5-F-pyridin-2-yl 1.5048 (26.8) A-43 4-t-Bu Me Me Me 5-Me-pyridin-2-yl 1.5302(22.2) A-44 4-(i-PrO) Me Me H Pyridin-2-yl 1.5368 (24.4) A-45 4-(i-PrO) Me Me H 5-Cl-pyridin-2-yl 1.5454 (24.6) A-46 4-(c-PenO) Me Me H Pyridin-2-yl NMR

[0127] [Table 1-3] Table 1 (Continued) Compound number (R 1 ) m R 2 R 3 R4 Q Physical property value A-47 4-(c-PenO) Me Me H 5-Cl-pyridin-2-yl 1.5560 (26.8) A-47a 4-(c-PenO) Me Me H 5-Cl-pyridin-2-yl A-47b 4-(c-PenO) Me Me H 5-Cl-pyridin-2-yl A-48 4-t-Bu Me Me H 6-Cl-pyridin-2-yl 137-139 A-49 4-t-Amyl Me Me H 6-Me-pyridin-2-yl 62-64 A-50 4-t-Amyl Me Me H 6-Cl-pyridin-2-yl 84-86 A-51 4-(i-PrO) Me Me H 6-Me-pyridin-2-yl NMR A-52 4-(i-PrO) Me Me H 6-Cl-pyridin-2-yl NMR A-53 4-(c-PenO) Me Me H 6-Me-pyridin-2-yl 1.4743 (26.3) A-54 4-(c-PenO) Me Me H 6-Cl-pyridin-2-yl NMR A-55 4-i-Pr Me Me H 6-Me-pyridin-2-yl 1.5357(26.1) A-55a 4-i-Pr Me Me H 6-Me-pyridin-2-yl A-55b 4-i-Pr Me Me H 6-Me-pyridin-2-yl A-56 4-i-Pr Me Me H 6-Cl-pyridin-2-yl NMR A-57 4-PhO Me Me H 6-Me-pyridin-2-yl 1.5297 (25.2) A-58 4-PhO Me Me H 6-Cl-pyridin-2-yl 1.5749 (25.1) A-59 4-Ph Me Me H 6-Me-pyridin-2-yl 1.5355 (25.1) A-60 4-Ph Me Me H 6-Cl-pyridin-2-yl 1.5189(25.2) A-61 4-CF3 Me Me H 5-Me-pyridin-2-yl 89-92 A-62 4-t-Bu Me Me H 5-Br-pyridin-2-yl 103-105 A-63 4-t-Bu Me Me H 3-Me-pyridin-2-yl NMR A-64 4-t-Bu Me Me H 4-Me-pyridin-2-yl NMR A-65 4-t-Bu Me Me H 6-F-pyridin-2-yl 82-84 A-65a 4-t-Bu Me Me H 6-F-pyridin-2-yl A-65b 4-t-Bu Me Me H 6-F-pyridin-2-yl A-66 4-t-Bu Me Me H 5-Me-pyrazine-2-yl 96-98 A-67 4-t-Bu Me Me H Pyrimidin-2-yl 122-124 A-68 4-t-Bu Me Me H 127-129 A-69 4-t-Amyl Me Me H 6-F-pyridin-2-yl 116-118 A-70 4-i-Pr Me Me H 6-F-pyridin-2-yl 105-107 (In the table, * indicates the junction.)

[0128] [Table 1-4] Table 1 (Continued) Compound number (R 1 ) m R 2 R 3 R 4 Q Physical property value A-71 4-(2-F-Ph) Me Me H Pyridin-2-yl NMR A-72 4-(2-F-Ph) Me Me H 6-Me-pyridin-2-yl NMR A-73 4-(2-F-Ph) Me Me H 6-F-pyridin-2-yl 123-125 A-74 4-(2-Me-Ph) Me Me H 6-Me-pyridin-2-yl NMR A-75 4-MeO Me Me H Pyridin-2-yl NMR A-76 4-MeO Me Me H 6-Me-pyridin-2-yl NMR A-77 4-MeO Me Me H 6-F-pyridin-2-yl NMR A-78 4-MeO Me Me H 6-Cl-pyridin-2-yl NMR A-79 4-t-Bu Me Me H 6-Br-pyridin-2-yl 114-116 A-80 4-i-Pr Me Me H 4-Me-pyridin-2-yl NMR A-81 4-t-Amyl Me Me H 4-Me-pyridin-2-yl NMR A-82 4-(2-F-PhO) Me Me H 6-Me-pyridin-2-yl NMR A-83 4-t-Bu Me Me H 6-c-Pr-pyridin-2-yl 114-116 A-84 4-t-Bu Me Me H 6-CN-pyridin-2-yl 80-82 A-85 4-(2,2-Dimethylpropyl) Me Me H 6-Me-pyridin-2-yl NMR A-86 4-(2,2-Dimethylpropyl) Me Me H Pyridin-2-yl NMR A-86a 4-(2,2-Dimethylpropyl) Me Me H Pyridin-2-yl A-86b 4-(2,2-Dimethylpropyl) Me Me H Pyridin-2-yl A-87 4-(t-BuO) Me Me H 6-Me-pyridin-2-yl NMR A-88 4-t-Bu Me H H 6-Me-pyridin-2-yl 1.5541 (17.7) A-89 4-CHF2 Me Me H 6-Me-pyridin-2-yl 1.5309 (16.3) A-90 4-(2,6-F2-Ph) Me Me H 6-Me-pyridin-2-yl NMR A-91 4-Br Me Me H Pyridin-2-yl A-92 4-Br Me Me H 6-Me-pyridin-2-yl A-93 4-Br Me Me H 6-F-pyridin-2-yl A-94 4-I Me Me H Pyridin-2-yl NMR A-95 4-I Me Me H 6-Me-pyridin-2-yl A-96 4-I Me Me H 6-F-pyridin-2-yl

[0129]

[0130] [Table 2] Table 2 compound serial number (R 1 ) m R 2 R 3 R 4 (R 5 ) n Physical property value B-1 5-CF3 Me Me H 5,6-diMe B-2 5-CF3 Me Me H 5-Me B-3 5-t-Bu Me Me H 6-Me B-4 5-t-Bu Me Me H H B-5 H Me Me H H NMR B-6 H Me Me H 6-Me NMR

[0131]

[0132] [Table 3] Table 3 compound serial number (R 1 ) m R 2 R 3 R 4 (R 5 ) n Physical property value C-1 6-CF3 Me Me H 5,6-diMe C-2 6-CF3 Me Me H 5-Me C-3 6-Cl Me Me H 5,6-diMe C-4 6-Cl Me Me H 5-Me C-5 6-Ph Me Me H 5,6-diMe C-6 6-Ph Me Me H 5-Me

[0133]

[0134] [Table 4] Table 4 compound serial number (R 1 ) m R 2 R 3 R 4 Q Physical property value D-1 4-t-Bu Me Me H 5-Me-pyridin-2-yl D-2 4-t-Bu Me Me H (In the table, * indicates the joint area.)

[0135]

[0136] [Table 5] Table 5 compound serial number (R 1 ) m R 2 R 3 Physical property value E-1 4-t-Bu Me Me NMR E-1a 4-t-Bu Me Me NMR E-1b 4-t-Bu Me Me E-2 4-i-Pr Me Me NMR E-3 4-t-pentyl Me Me NMR E-4 4-Ph Me Me E-5 4-PhO Me Me E-6 4-(2-Me-PhO) Me Me E-7 4-(2-F-PhO) Me Me E-8 4-(2-OMe-PhO) Me Me E-9 4-(i-PrO) Me Me E-10 4-(c-PenO) Me Me E-11<000138​​​​​​​​​​​​​​​​​​​​​​​​4-(t-BuO) Me Me E-15 4-CHF2 Me Me E-16 4-(2,6-F2-Ph) Me Me E-17 4-I Me Me E-18 4-t-Bu H H

[0137] [Table 6-1] Table 6 compound serial number 1 H-NMR data (CDCl3 / TMS, ppm) A-2 δ 7.57(d, 2H), 7.40(d, 2H), 7.35(d, 1H), 6.97(d, 1H), 4.48(d, 2H), 3.27(d, 1H), 3.10(d, 1H), 2.46(s, 3H), 2.52(s, 3H), 1.31(s, 9H) A-3 δ 7.75(t, 1H), 7.51(d, 2H), 7.33(d, 2H), 7.12(d, 1H), 7.00(d, 1H), 4.58(dd, 2H),2.51(s, 3H), 2.32(s, 3H), 1.32(s, 3H), 1.29(s, 9H), 1.02(s, 3H) A-4 δ 8.56(d, 1H), 7.63(ddd, 1H), 7.55(d, 2H), 7.53-7.48(m, 1H), 7.36(t, 2H), 7.22(d, 1H), 7.18(dd, 1H), 4.65-4.41(m, 2H), 1.42(s, 3H), 1.30(s, 9H), 1.07(s, 3H) A-5 δ 8.56(d, 1H), 7.66-7.58(m, 3H), 7.55-7.49(m, 1H), 7.36-7.30(m, 2H), 7.23(d, 1H), 7.19(dd, 1H), 7.10(t, 1H), 7.01(d, 2H), 6.98(d, 2H), 4.66-4.43(m, 2H), 1.45(s, 3H), 1.09(s, 3H) A-6 δ 7.61(d, 2H), 7.50-7.44(m, 1H), 7.36-7.30(m, 3H), 7.13-7.08(m, 1H), 7.03-6.94(m, 5H), 4.59-4.34(m, 2H), 2.48(s, 3H), 2.25(s, 3H), 1.46(s, 3H), 1.09(s, 3H) A-7 δ 8.37(d, 1H), 7.61(d, 2H), 7.49-7.42(m, 2H), 7.36-7.30(m, 2H), 7.13-7.08(m, 2H), 7.01(dd, 2H), 6.98(d, 2H), 4.61-4.38(m, 2H), 2.32(s, 3H), 1.44(s, 3H), 1.08(s, 3H) A-8 δ 8.42(d, 1H), 7.60(d, 2H), 7.43-7.30(m, 4H), 7.13-7.08(m, 1H), 7.03-6.96(m, 4H), 4.65-4.40(m, 2H), 1.43(s, 3H), 1.09(s, 3H) A-10 δ 8.55(d, 1H), 7.63(ddd, 1H), 7.55(d, 2H), 7.53-7.49(m, 1H), 7.25-7.17(m, 4H), 4.61(dd, 1H), 4.65-4.41(dd, 1H), 2.89(quin, 1H), 1.42(s, 3H), 1.23(d, 6H), 1.06(s, 3H)

[0138] [Table 6-2] Table 6 (Continued) compound Number 1 H-NMR data (CDCl3 / TMS, ppm) A-11 δ 8.36 (d, 1H), 7.54 (d, 2H), 7.48 - 7.41 (m, 2H), 7.19 (d, 2H), 7.13 (d, 1H), 4.60 - 4.36 (m, 2H), 2.89 (quin, 1H), 2.32 (s, 3H), 1.41 (s, 3H), 1.23 (d, 6H), 1.06 (s, 3H) A-12 δ 8.39 (d, 1H), 7.54 (d, 2H), 7.42 - 7.37 (m, 1H), 7.38 (ddd, 1H), 7.24 (dd, 1H), 7.20 (d, 2H), 4.63 - 4.39 (m, 2H), 2.90 (quin, 1H), 1.41 (s, 3H), 1.24 (d, 6H), 1.07 (s, 3H) A-15 δ 7.56 (d, 2H), 7.51 (t, 1H), 7.50 - 7.46 (m, 1H), 7.36 (d, 2H), 7.02 (t, 2H), 4.63 - 4.35 (m, 2H), 2.55 (s, 3H), 1.46 (s, 3H), 1.31 (s, 9H) A-17 δ 8.55 (d, 2H), 7.62 (ddd, 1H), 7.56 (d, 2H), 7.53 - 7.48 (m, 1H), 7.30 (d, 2H), 7.21 (d, 1H), 7.18 (dd, 1H), 4.66 - 4.41 (m, 2H), 1.62 (t, 2H), 1.44 (s, 3H), 1.26 (s, 6H), 1.07 (s, 3H), 0.655 (t, 3H) A-18 δ 8.37 (d, 1H), 7.55 (d, 2H), 7.47 - 7.41 (m, 2H), 7.29 (d, 2H), 7.11 (d, 1H), 4.61 - 4.36 (m, 2H), 2.31 (s, 3H), 1.62 (t, 2H), 1.43 (s, 3H), 1.26 (s, 6H), 1.06 (s, 3H), 0.65 (t, 3H) A-19 δ 7.56(d, 2H), 7.48-7.42(m, 1H), 7.32(d, 1H), 7.29(d, 2H), 6.94(d, 1H), 4.58-4.32(m, 2H), 2.48(s, 3H), 2.25(s, 3H), 2.05(s, 3H), 1.62(q, 2H), 1.45(s, 3H), 1.26(s, 6H), 1.06(s, 3H), 0.66(t, 3H) A-21 δ 7.55(d, 2H), 7.47-7.42(m, 1H), 7.33(d, 1H), 7.20(d, 2H), 6.95(d, 1H), 4.58-4.31(m, 2H), 2.89(quin, 1H), 2.48(s, 3H), 2.24(s, 3H), 1.45(s, 3H), 1.23(d, 6H), 1.07(s, 3H) A-27 δ 8.51(d, 1H), 7.64-7.57(m, 3H), 7.43-7.37(m, 1H), 7.33(t, 2H), 7.19(d, 1H), 7.11(t, 1H), 7.00(d, 2H), 6.98(d, 2H), 4.64-4.40(m, 2H), 1.44(s, 3H), 1.09(s, 3H) A-40 δ 7.40(d, 1H), 7.33(d, 2H), 6.96-6.89(m, 2H), 6.82(d, 2H), 4.74(quin, 1H), 4.53-4.36(m, 2H), 2.42(s, 3H), 2.24(s, 3H), 1.94-1.75(m, 6H), 1.65-1.58(m, 2H), 1.30(s, 3H), 1.11(s, 3H) A-46 δ 8.58(d, 1H), 8.48(d, 1H), 7.40(t, 1H), 7.33(d, 2H), 7.17(t, 1H), 6.55(br, 1H), 6.82(d, 2H), 4.73(quin, 1H), 4.66-4.43(m, 2H), 1.94-1.73(m, 6H), 1.65-1.58(m, 2H), 1.32(s, 3H), 1.08(s, 3H)

[0139] [Table 6-3] Table 6 (continued) compound serial number 1 H-NMR data (CDCl3 / TMS, ppm) A-51 δ 7.51(t, 1H), 7.34(d, 2H), 7.19(d, 1H), 7.04-6.92(m, 3H), 6.84(d, 2H), 4.58-4.41(m, 2H), 2.48(s, 3H), 1.33 (d, 6H), 1.30(s, 3H), 1.11(s, 3H) A-52 δ 7.60(t, 1H), 7.31(d, 2H), 7.22(d, 1H), 7.12(d, 1H), 6.85(d, 2H), 6.71(br, 1H), 4.59-4.43(m, 3H), 1.33(d, 6H), 1.31(s, 3H), 1.09(s, 3H) A-54 δ 8.44(d, 1H), 7.61(dd, 2H), 7.30(d, 2H), 7.14(d, 1H), 6.85-6.75(m, 3H), 4.73(quin, 1H), 4.60-4.41(m, 2H), 1.96-1.73(m, 6H), 1.67-1.56(m, 2H), 1.30(s, 3H), 1.09(s, 3H) A-56 δ 7.58(t, 1H), 7.54(d, 2H), 7.23-7.18(m, 4H), 7.15(d, 1H), 4.63-4.34(m, 2H), 2.89(quin, 1H), 1.45(s, 3H), 1.24(d, 6H), 1.07(s, 3H) A-63 δ 8.41(d, 1H), 8.16-8.10(m, 1H), 7.60(d, 2H), 7.44(d, 1H), 7.36(d, 2H), 7.14-7.09(m, 1H), 4.59-4.34(m, 2H), 2.26(s, 3H), 1.47(s, 3H), 1.30(s, 9H), 1.10(s, 3H) A-64 δ 8.39(d, 1H), 7.56(d, 2H), 7.47(br, 1H), 7.36(d, 2H), 7.03-6.97(m, 2H), 4.59-4.36(m, 2H), 2.30(s, 3H), 1.44(s, 3H), 1.31(s, 9H), 1.08(s, 3H) A-71 δ 8.56(d, 1H), 7.73(d, 2H), 7.64(ddd, 1H), 7.57-7.51(m, 3H), 7.43(ddd, 1H), 7.34-7.28(m, 1H), 7.25-7.11(m, 4H), 4.67-4.44(m, 2H), 1.48(s, 3H), 1.12(s, 3H) A-72 δ 7.74(d, 2H), 7.57-7.49(m, 4H), 7.43(ddd, 1H), 7.31(br, 1H), 7.23-7.10(m, 2H), 7.03(t, 2H), 4.64-4.38(m, 2H), 2.55(s, 3H), 1.50(s, 3H), 1.13(s, 3H) A-74 δ 7.69(d, 2H), 7.55-7.49(m, 2H), 7.31(d, 2H), 7.26-7.20(m, 4H), 7.06-7.01(m, 2H), 4.65-4.39(m, 2H), 2.55(s, 3H), 2.26(s, 3H), 1.49(s, 3H), 1.13(s, 3H) A-75 δ 8.48(d, 1H), 7.64(ddd, 1H), 7.38(d, 2H), 7.21-7.15(m, 2H), 6.94(br, 1H), 6.86(d, 2H), 4.67-4.43(m, 2H), 3.80(s, 3H), 1.33(s, 3H), 1.07(s, 3H) A-76 δ 7.51(t, 1H), 7.37(d, 2H), 7.02(d, 1H), 6.97(d, 1H), 6.93(br, 1H), 6.87(d, 2H), 4.58-4.41(m, 2H), 3.80(s, 3H), 2.48(s, 3H), 1.13(s, 3H), 1.10(s, 3H) A-77 δ 7.73(t, 1H), 7.35(d, 2H), 7.07(dd, 1H), 6.87(d, 2H), 6.82(dd, 1H), 6.65(br, 1H), 4.60-4.39(m, 2H), 3.80(s, 3H), 1.32(s, 3H), 1.07(s, 3H) A-78 δ 7.60(t, 1H), 7.34(d, 2H), 7.22(d, 1H), 7.12(d, 2H), 6.87(d, 2H), 6.70(br, 1H), 4.59(m, 2H), 3.60(s, 3H), 1.31(s, 3H), 1.08(s, 3H) A-80 δ 8.39(d, 1H), 7.55(d, 2H), 7.51-7.43(m, 1H), 7.20(d, 2H), 7.03-6.97(m, 2H), 4.59-4.36(m, 2H), 2.89(quin, 1H), 2.29(s, 3H), 1.44(s, 3H), 1.23(d, 6H), 1.07(s, 3H) A-81 δ 8.39(d, 1H), 7.56(d, 2H), 7.50-7.44(m, 1H), 7.29(d, 2H), 7.00(br, 1H), 4.60-4.37(m, 2H), 2.30(s, 3H), 1.63(t, 2H), 1.44(s, 3H), 1.27(s, 6H), 1.07(s, 3H), 0.657(t, 3H)

[0140] [Table 6-4] Table 6 (continued) compound serial number 1 H-NMR data (CDCl3 / TMS, ppm) A-82 δ 7.61(d, 2H), 7.56-7.45(m, 2H), 7.20-6.99(m, 6H), 6.95(d, 2H), 4.62-4.37(m, 2H), 2.54(s, 3H), 1.46(s, 3H), 1.08(s, 3H) A-85 δ 7.53(d, 2H), 7.52-7.45(m, 2H), 7.10(d, 2H), 7.04-7.00(m, 2H), 4.62-4.37(m, 2H), 2.53(s, 3H), 2.48(s, 2H), 1.45(s, 3H), 1.06(s, 3H), 0.89(s, 9H) A-86 δ 8.56-8.54(m, 1H), 7.62(dt, 1H), 7.55-7.48(m, 3H), 7.22-7.16(m, 2H), 7.10(d, 2H), 4.65-4.43(m, 2H), 2.48(s, 2H), 1.44(s, 3H), 1.06(s, 3H), 0.89(s, 9H) A-87 δ 7.54(d, 2H), 7.51-7.44(m, 2H), 7.02(t, 2H), 6.96(d, 2H), 4.63-4.37(m, 2H), 2.54(s, 3H), 1.45(s, 3H), 1.34(s, 9H), 1.05(s, 3H) A-90 δ 7.76(d, 2H), 7.60-7.44(m, 5H), 7.06-6.95(m, 4H), 4.64-4.39(m, 2H), 2.54(s, 3H), 1.49(s, 3H), 1.13(s, 3H) A-94 δ 8.55(d, 1H), 7.68(d, 2H), 7.63(ddd, 1 H),7.51(br, 1H), 7.41(d, 2H), 7.23-7.16(m, 2H), 4.64-4.41(m, 2H), 1.44(s, 3H), 1.06(s, 3H) B-5 δ 8.64-8.60(m, 1H), 8.57-8.54(m, 1H), 8.27(br, 1H), 7.71(ddd, 1H), 7.66-7.60(m, 2H), 7.26-7.20(m, 2H), 7.20-7.15(m, 1H), 4.60(dd, 2H), 1.50(s, 3H), 1.08(s, 3H) B-6 δ 8.63(d, 1H), 8.28(br, 1H), 7.74-7.63(m, 2H), 7.50(t, 1H), 7.26-7.23(m, 1H), 7.05-7.00(m, 2H), 4.55(dd, 2H), 2.56(s, 3H), 1.52(s, 3H), 1.07(s, 3H) E-1 δ 7.51(d, 2H), 7.35(d, 2H), 1.54(s, 3H), 1.31(s, 9H), 1.10(s, 3H) E-1a δ 7.51(d, 2H), 7.35(d, 2H), 1.54(s, 3H), 1.31(s, 9H), 1.10(s, 3H) E-2 δ 7.49(d, 2H), 7.21(d, 2H), 2.90(quin, 1H), 1.50(s, 3H), 1.24(d, 6H), 1.08(s, 3H) E-3 δ 7.50(d, 2H), 7.33(d, 2H), 1.63(q, 2H), 1.55(s, 3H), 1.28(s, 6H), 1.09(s, 3H), 0.66(t, 3H)

[0141] Agro-horticultural fungicides containing compounds of the general formula [I] or their salts as active ingredients are suitable for the prevention and control of diseases occurring in cereals, fruit trees, vegetables, other crops and flowers.

[0142] Examples of diseases that can be identified include filamentous fungal diseases, bacterial diseases, and viral diseases. Examples of filamentous fungal diseases include, for instance, incomplete fungi (e.g., diseases of the genera *Botrytis*, *Helminthosporium*, *Fusarium*, *Septoria*, *Cercospora*, *Pyricularia*, *Alternaria*, etc.), basidiomycetes (e.g., diseases of the genera *Hemileia*, *Rhizoctonia*, *Puccinia*, etc.), and ascomycetes (…). For example, diseases of the genera *Venturia*, *Podosphaera*, *Leptosphaeria*, *Blumeria*, *Erysiphe*, *Microdochium*, *Sclerotinia*, *Gaeumannomyces*, *Monilinia*, *Uncinula*, etc., and other fungi (e.g., diseases of *Ascochyta*, *Phoma*, *Pythium*, *Corticium*, *Pyrenophora*, etc.). Examples of bacterial diseases include those caused by Pseudomonas, Xanthomonas, and Erwinia. Examples of viral diseases include those caused by Tabacco mosaic virus.

[0143] Specific diseases caused by filamentous fungi include, for example, rice blast (Pyricularia oryzae), rice sheath blight (Rhizoctonia solani), rice intercalation blight (Cochliobolus miyabeanus), rice seedling damping-off (Rhizopus chinensis), *Pythium graminicola*, *Fusarium graminicola*, *Fusarium roseum*, *Mucor sp.*, *Phoma sp.*, *Tricoderma sp.*), rice seedling blight (Gibberella fujikuroi), powdery mildew of barley and wheat (*Blumeria graminis*), powdery mildew of cucumbers (*Sphaerotheca fuliginea*), and powdery mildew of eggplants (*Erysiphe*). Powdery mildew of other host plants, eye spot of barley and wheat (Pseudocercosporella herpotrichoides), wheat smut (Urocystis tritici), snow blight of barley and wheat (Microdochium nivalis, Pythium iwayamai, Typhla ishikariensis, Typhla incarnata, Sclerotinia borealis), red mold of barley (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivalis), and rust of barley and wheat (Puccinia rust). Recondita, black rust (Puccinia striiformis), stem rust (Puccinia graminis), damping-off of barley and wheat (Gaeumannomyces graminis), crown rot of oats (Puccinia coronata), and rust diseases of other plants, as well as gray mold of cucumbers and strawberries (Botrytis cinerea).Cinerea), sclerotinia sclerotiorum (sclerotinia sclerotiorum) of cucumbers and tomatoes, late blight (Phytophthora infestans) of potatoes and tomatoes, and late blight of other plants; downy mildew (Pseudoperonospora cubensis) of cucumbers, downy mildew (Plasmopara viticola) of grapes, and various other plant downy mildew; Venturia inaequalis (Venturia inaequalis) of apples, Alternaria mali (Alternaria mali) of apples, Botryosphaeria berengeriana (Botryosphaeria berengeriana) of apples, late rot of grapes (Colletotrichum gloeosporioides, Colletotrichum acutatum) of grapes, Elsinoe ampelina (Elsinoe ampelina) of grapes, Alternaria kikuchiana (Alternaria kikuchiana) of pears, and Diaporthe (Diaporthe) of citrus. Citrus scab fungus (Elsinoe fawcetti), cucumber anthracnose (Colletotrichum lagenarium), beet brown spot fungus (Cercospora beticola), peanut brown spot fungus (Cercospora arachidicola), peanut black spot fungus (Cercospora personata), wheat leaf spot fungus (Septoria tritici), wheat glume blight fungus (Leptosphaeria nodorum), barley netting fungus (Pyrenophora teres), barley leaf spot fungus (Pyrenophora graminea), barley cloud spot fungus (Rhynchosporium secalis), wheat naked smut (Ustilago nuda), wheat smut fungus (Tilletia caries), turf leaf rot (Rhizoctonia solani), turf silver spot (Sclerotinia sclerotinia). (Homo spp.) Chinese cabbage black spot (Alternaria brassicola), tomato blight (Phytophthora infestans), cucumber gray mold (Botrytis cinerea), barley powdery mildew (Blumeria graminis f. sp.)Hordei, acute soybean wilt (Fusarium virguliforme), and sclerotinia sclerotirum (Sclerotinia sclerotirum), among others.

[0144] Specific bacterial diseases include those caused by the genus *Pseudomonas*, such as bacterial spot disease of cucumber (*Pseudomonas syringae pv. lachrymans*), bacterial wilt disease of tomato (*Pseudomonas solanacearum*), and bacterial glume blight of rice (*Pseudomonas glumae*). Diseases caused by the genus *Xanthomonas*, such as black rot of cabbage (*Xanthomonas campestris*), bacterial blight of rice (*Xanthomonas oryzae*), and citrus canker (*Xanthomonas citri*). Diseases caused by the genus *Erwinia*, such as soft rot of cabbage (*Erwinia erythrorhizon*). (carotovora), etc.

[0145] As a specific example of viral diseases, tobacco mosaic virus can be cited.

[0146] Among them, the agricultural and horticultural fungicide containing the compound or its salt as the active ingredient of the present invention general formula [I] is effective against filamentous fungal diseases, especially black spot of Chinese cabbage (Alternaria brassicola), tomato blight (Phytophthora infestans), gray mold of cucumber (Botrytis cinerea), anthracnose of cucumber (Colletotrichum lagenarium), rice blast (Pyricularia oryzae), apple scab (Venturia inaequalis), powdery mildew of barley (Blumeria graminis f. sp. Hordei), leaf spot fungus of wheat (Septoria tritici), sclerotinia sclerotiorum, ring rot of apple (Botryosphaeria berengeriana), late rot of grape (Colletotrichum gloeosporioides, Colletotrichum acutatum), and acute wilt of soybean (Fusarium). High efficacy was shown in the treatment of diseases such as *Virguliforme*, wheat red mold (*Fusarium graminearum*), cruciferous sclerotinia (*Sclerotinia sclerotirum*), and rice internode blight (*Cochliobolus miyabeanus*).

[0147] Furthermore, agricultural and horticultural fungicides containing compounds of the general formula [I] or their salts as active ingredients can be used, in addition to their use as fungicides, alone, in combination, or in mixtures as insecticides for the control of various agricultural, forestry, horticultural, stored grain diseases, sanitary diseases, or nematode diseases that harm rice, fruit trees, vegetables, other crops, and flowers. Examples of diseases or nematodes are as follows. Examples of diseases affecting Lepidoptera (Butterflies) include: *Parasa consocia*, *Anomis mesogona*, *Papilio xuthus*, *Matsumuraeses azukivora*, *Ostrinia scapulalis*, *Spodoptera exempta*, *Hyphantria cunea*, *Ostrinia furnacalis*, *Pseudaletia separata*, *Tinea translucens*, *Bactra furfuryla*, *Parnara guttata*, *Marasmia exigua*, *Parnara guttata*, *Sesamia inferens*, *Brachmia triannulella*, and *Monema*. flavescens, Trichoplusia ni, Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Cephonodes hylas, Helicoverpa armigera, Phalerodonta manleyi, Eumeta japonica, Malocosoma neustria testacea, Stathmopoda masinissa, Cuphodes diospyrosella, Archipelago xylosteanus, Agrotis segetum, Tetramoera schistaceana, Papilio machaon hippocrates, EndoclytaThe following are listed: *Sinensis*, *Lyonetia prunifoliella*, *Phyllonorycter ringoneella*, *Cydia kurokoi*, *Eucoenogenes aestuosa*, *Lobesia botrana*, *Latoia sinica*, *Euzophera batangensis*, *Phalonidia mesotypa*, *Spilosoma imparilis*, *Glyphodes pyloalis*, *Olethreutes mori*, *Tineola bisselliella*, *Endoclyta excrescens*, *Nemapogon granellus*, *Synanthedon hector*, *Cydia pomonella*, and *Plutella xanthipes*. xylostella, Cnaphalocrocis medinalis, Sesamia calamistis, Scirpophaga incertulas, Pediasia teterrellus, Phthorimaea operculella, Staurops fagi persimilis, Etiella zinckenella, Spodoptera exigua, Palpifer sexnotata, Spodoptera mauritia, Scirpophaga innotata, Xestia c-nigrum, Spodoptera depravata, Ephestia kuehniella, Angelona prunaria, Clostera anastomosis), soybean borer (Pseudoplusia includens), Matsumura's leafroller (Matsumuraeses falcana), tobacco bollworm (Helicoverpa assulta), black-spotted silver-striped borer (Autographa)The following are listed: *nigrisigna*, cutworm (Agrotis ipsilon), tea tussock moth (Euproctis pseudoconspersa), tea leafroller (Adoxophyes orana), tea leaf roller (Caloptilia theivora), tea leafroller (Homona magnanima), tobacco powdery borer (Ephestia elutella), tea debt moth (Eumeta minuscula), end-of-life moth (Clostera anachoreta), reed fruit moth (Heliothis maritima), grape leafroller (Sparganothis pilleriana), brown borer (Busseola fusca), white-spotted yellow tussock moth (Euproctis subflava), white-capped bulrush (Biston robustum), corn ear borer (Heliothis zea), white-tailed moth (Aedia leucomelas), pear tussock moth (Narosoideus flavidorsalis), pear sword-striped moth (Viminia rumicis), pear leafminer (Bucculatrix). Pyrivorella, Peach Heartworm (Grapholita molesta), Pear Leafminer (Spulerina astaurota), Pear Leaf Moth (Ectomyelois pyrivorella), Rice Stem Moth (Chilo suppressalis), Onion Leafminer (Acrolepiopsis sapporensis), Indian Rice Moth (Plodia interpunctella), Chinese Rice Moth (Hellula undalis), Wheat Moth (Sitotroga cerealella), Spodoptera litura, Bean Sprout Moth (Eucosma aporema), Strawberry Longwing Roller (Acleris comariana), Spherical Tussock Moth (Scopelodes contractus), Turtle Moth (Orgyia thyellina), Fall Armyworm (Spodoptera frugiperda), Ostrinia zaguliaevi, Red-banded Yellow Armyworm (Naranga aenescens), Tea Silkworm (Andraca) * bipunctata*, *Paranthrene regalis*, *Acosmeryx castanea*, *Phyllocnistis*Toparcha, grape fruit borer (Endopiza viteana), grape and apple leafroller (Eupoecillia ambiguella), soybean cutworm (Anticarsia gemmatalis), gray leafroller (Cnephasia cinereipalpana), gypsy moth (Lymantria dispar), red pine caterpillar (Dendrolimus spectabilis), soybean pod borer (Leguminivora glycinivorella), bean pod borer (Maruca testulalis), soybean leafroller (Matsumuraeses phaseoli), soybean leafminer (Caloptilia soyella), citrus leafminer (Phyllocnistis citrella), three-striped leaf borer (Omiodes indicate), apricot leafroller (Archips fuscocupreanus), silver-striped cutworm (Acanthoplusia agnata), bagworm (Bambalina sp.), peach fruit borer (Carposina) This includes species such as *Prunus niponensis*, *Conogethes punctiferalis*, *Synanthedon* sp., *Lyonetia clerkella*, *Papilio helenus*, *Colias erate poliographus*, *Phalera flavescens*, *Pieris brassicae*, *Pieris rapae crucivora*, etc., belonging to the Pieridae family; *Euproctis similis*, *Acrolepiopsis suzukiella*, *Ostrinia nubilalis*, *Mamestra brassicae*, *Ascotis selenaria*, *Phtheochroides clandestina*, *Hoshinoa adumbratana*, and *Odonestis*. Apple leafroller (Prunus pruni japonensis), apple sword-striped moth (Triaena intermedia), apple leafroller (Adoxophyes orana fasciata), apple fruit borer (Grapholita inopinata), apple white leafroller (Spilonota)The following are listed as pests: ocellana, apple leafroller (Spilonota lechriaspis), pear star-shaped caterpillar (Illiberis pruni), apple silver moth (Argyresthia conjugella), apple leafminer (Caloptilia zachrysa), pear yellow leafroller (Archips breviplicanus), small bridge-building moth (Anomis flava), cotton red bollworm (Pectinophora gossypiella), cotton large leafroller (Notarcha derogata), melon silkworm moth (Diaphania indica), tobacco bud moth (Heliothis virescens), and ding-point borer (Earias cupreoviridis).

[0148] As diseases of the order Hemiptera (Stink Bugs), examples include the Oriental Green Bug (Nezara antennata), Red-striped Mirid Bug (Stenotus rubrovittatus), Black-striped Red Stink Bug (Graphosoma rubrolineatum), Red-bearded Mirid Bug (Trigonotylus coelestialium), etc., Red-edged Stink Bug (Aeschynteles maculatus), Red-spotted Mirid Bug (Creontiades pallidifer), Red-spotted Stink Bug (Dysdercus cingulatus), Brown Round Scale Insect (Chrysomphalus ficus), Orange-red Kidney Shield Scale Insect (Aonidiella aurantii), Japanese Oil Cicada (Graptopsaltria nigrofuscata), Wheat Long Stink Bug (Blissus leucopterus), Blossomyces purchasi, White-walled Stink Bug (Piezodorus hybneri), and Rice Stink Bug (Lagynotomus). *Elongatus*, *Thaia subrufa*, *Scotinophara lurida*, *Sitobion ibarae*, *Stariodes iwasakii*, *Aspidiotus destructor*, *Taylorilygus pallidulus*, *Myzus umecola*, *Pseudaulacaspis prunicola*, *Acyrthosiphon pisum*, *Anacanthocoris striicornis*, *Ectometopterus micantulus*, *Eysarcoris lewisi*, *Molipteryx fuliginosa*, *Cicadella viridis*, *Rhopalosophum* *Rufiabdominalis*, *Saissetia oleate*, *Trialeurodes vaporariorum*, *Aguriahana quercus*, *Lygus spp.*, *Euceraphis punctipennis*, and *Andaspis* (citrus scale insects)kashicola, orange scale insect (Coccus pseudomagnoliarum), small-winged stink bug (Cavelerius saccharivorus), leaf-backed lace bug (Galeatus spinifrons), smoky brown chrysanthemum aphid (Macrosiphoniella sanborni), orange kidney-shaped scale insect (Aonidiella citrina), tea-winged stink bug (Halyomorpha mista), spotted crown lace bug (Stephanitis fasciicarina), camphor leafhopper (Trioza camphorae), mid-season rice edged stink bug (Leptocorisa chinensis), oak psyllid (Trioza quercicola), walnut maggot (Uhlerites latius), grape leafhopper (Erythroneura comes), black-legged slender stink bug (Paromius exiguus), black hard round scale insect (Duplaspidiotus claviger), two-tailed black-tailed leafhopper (Nephotettix nigropictus), black-brown mirid stink bug (Halticiellus) The following insects are listed: *Psylla malivorella*, *Anomomeura mori*, *Pseudococcus longispinis*, *Pseudaulacaspis pentagona*, *Pulvinaria kuwacola*, *Apolygus lucorum*, *Togo hemipterus*, *Toxoptera aurantii*, *Saccharicoccus sacchari*, *Geoica lucifuga*, *Numata muiri*, *Comstockaspis perniciosa*, *Unaspis citri*, *Aulacorthum solani*, and *Eysarcoris*. Ventralis, silver leafhopper (Bemisia argentifolii), large white leafhopper (Cicadella spectra), ivy scale insect (Aspidiotus hederae), chestnut stink bug (Liorhyssus)Hyalinus, Calophya nigridorsalis, Sogatella furcifera, Megoura crassicauda, ​​Brevicoryne brassicae, Aphis glycines, Leptocorisa oratorius, Nephotettix virescens, Uroeucon formosanum, Cyrtopeltis tennuis, Bemisia tabaci, Lecanium persicae, Parlatoria theae, Pseudaonidia paeoniae, Empoasca onukii, Plautia stali, Dysaphis tulipae, Macrosiphum The following insects are listed: euphorbiae, Stephanitis pyrioides, Ceroplastes ceriferus, Parlatoria camelliae, Apolygus spinolai, Nephotettix cincticeps, Glaucias subpunctatus, Orthotylus flavosparsus, Rhopalosiphum maidis, Peregrinus maidis, Eysarcoris parvus, Cimex lectularius, Psylla abieti, Nilaparvata lugens, Psylla tobirae, Eurydema rugosum, Schizaphis piricola, and Psylla spp. pyricola), pear scale insect (Parlatoreopsis pyri), pear crown lace bug (Stephanitis nashi), pear powdery scale insect (Dysmicoccus wistariae), pear scale insect (Lepholeucaspis)Japonica aphid (Sappaphis piri), Lipaphis erysimi, Neotoxoptera formosana, Rhopalosophum nymphaeae, Edwardsianarosae, Pinnaspisaspidistrae, Psylla alni, Speusotettix subfusculus, Alnetoidia alneti, Sogatella panicicola, Adelphocoris lineolatus, Dysdercus poecilus, Parlatoria ziziphi, Uhlerites debile, Laodelphax striatella, Eurydema pulchrum, Cletus *Clovia punctata*, *Empoasca sp.*, *Coccus hesperidum*, *Pachybrachius luridus*, *Planococcus kraunhiae*, *Stenotus binotatus*, *Arboridia apicalis*, *Macrosteles fascifrons*, *Dolycoris baccarum*, *Adelphocoris triannulatus*, *Viteus vitifolii*, *Acanthocoris sordidus*, *Leptocorisa acuta*, *Macropes obnubilus*, *Cletus punctiger*, *Riptortus* clavatus, potato psyllid (Paratrioza cockerelli), yellow fleahopper (Aphrophora costalis), leafroller weevil (Lygus disponsi), spotted weevil (Lygus saundersi), pine powder scale insect (Crisicoccus pini), pine leafhopper (Empoasca)abietis, pine powdery scale insect (Crisicoccus matsumotoi), bean aphid (Aphis craccivora), round stink bug (Megacopta punctatissimum), round white star stink bug (Eysarcoris guttiger), oyster shield scale insect (Lepidosaphes beckii), citrus psyllid (Diaphorina citri), large citrus aphid (Toxoptera citricidus), citrus powdery scale insect (Planococcus citri), citrus naked whitefly (Dialeurodes citri), citrus spiny whitefly (Aleurocanthus spiniferus), citrus small powdery scale insect (Pseudococcus citriculus), mandarin orange leafhopper (Zyginella citri), mandarin orange cottony scale insect (Pulvinaria citricola), citrus scale insect (Coccus discrepans), camellia round scale insect (Pseudaonidia duplex), citrus cottony scale insect (Pulvinaria) aurantii, Lecanium corni, Nezara viridula, Stenodema calcaratum, Rhopalosiphum padi, Sitobion akebiae, Schizaphis graminum, Sorhoanus tritici, Brachycaudus helichrysi, Carpocoris purpureipennis, Myzus persicae, Hyalopterus pruni, Aphis farinose yanagicola, Metasalis populi, Unaspis yanonensis, Mesohomotoma camphorae, Aphis spiraecola, Aphis philodendron pomi), apple elm scale insect (Lepidosaphes ulmi), apple psyllid (Psylla mali), apple black blind stink bug (Heterocordylus flavipes), apple gall aphid (Myzus malisuctus), apple aphid (Aphidonuguis)The aphids include mali, orientus ishidai, malicolens, eriosoma lanigerum, ceroplastes rubens, and aphis gossypii.

[0149] As diseases of the order Coleoptera (insects), examples include: *Xystrocera globosa*, *Paederus fuscipes*, *Eucetonia roelofsi*, *Callosobruchus chinensis*, *Cylas formicarius*, *Hypera postica*, *Echinocnemus squameus*, *Oulema oryzae*, *Donacia provosti*, *Lissorhoptrus oryzophilus*, *Colasposoma dauricum*, *Euscepes postfasciatus*, *Epilachna varivestis*, *Acanthoscelides obtectus*, and *Diabrotica*. The following species are listed: *Vibrifera virgifera*, *Involvulus cupreus*, *Aulacophora femoralis*, *Bruchus pisorum*, *Epilachna vigintioctomaculata*, *Carpophilus dimidiatus*, *Cassida nebulosa*, *Luperomorpha tunebrosa*, *Phyllotreta striolata*, *Psacothea hilaris*, *Aeolesthes chrysothrix*, *Curculio sikkimensis*, *Carpophilus hemipterus*, *Oxycetonia jucunda*, and *Diabrotica spp.*The following are listed: * *Mimela splendens*, *Sitophilus zeamais*, *Tribolium castaneum*, *Sitophilus oryzae*, *Palorus subdepressus*, *Melolontha japonica*, *Anoplophora malasiaca*, *Neatus picipes*, *Leptinotarsa ​​decemlineata*, *Diabrotica undecimpunctata howardi*, *Sphenophorus venatus*, *Crioceris quatuordecimpunctata*, *Conotrachelus nenuphar*, *Ceuthorhynchidius albosuturalis*, *Phaedon brassicae*, and *Lasioderma*. The following are listed: * *serricorne*, *Sitona japonicus*, *Adoretus tenuimaculatus*, *Tenebrio molitor*, *Basilepta balyi*, *Hypera nigrirostris*, *Chaetocnema concinna*, *Anomala cuprea*, *Heptophylla picea*, *Epilachna vigintioctopunctata*, *Diabrotica longicornis*, *Eucetonia pilifera*, and *Agriotes spp.*), Black hairy beetle (Attagenus unicolor japonicus), Spotted beetle (Pagria signata), Red copper beetle (Anomala rufocuprea), Powder beetle (Palorus ratzeburgii), Powder beetle (Alphitobius laevigatus), Powder beetle (Anthrenus verbasci), Brown powder beetle (Lyctus brunneus), Mixed powder beetle (Tribolium confusum), Two-striped beetle (Medythia nigrobilineata), Grape longhorn beetle (Xylotrechus pyrrhoderus), Cucumber flea beetle (Epitrix cucumeris), Pit-cutting beetle (Tomicus piniperda), Pine longhorn beetle (Monochamus alternatus), Japanese beetle (Popillia japonica), Bean blister beetle (Epicauta gorhami), Corn weevil (Sitophilus) The following are examples of weevils: *Zeamais*, *Rhynchites heros*, *Listroderes costirostris*, *Callosobruchus maculatus*, *Phyllobius armatus*, *Anthonomus pomorum*, *Linaeidea aenea*, and *Anthonomus grandis*.

[0150] As diseases affecting Diptera (flies), examples include Culex pipiens pallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae, Hydrellia sasakii, Agromyza oryzae, Hydrellia griseola, Hydrellia griseola, Ophiomyia phaseoli, Dacus cucurbitae, Drosophila suzukii, Rhacochlaena japonica, Muscina stabulans, and Megaselia. The species include spiracularis (a type of leaf beetle), Clogmia albipunctata (a white spot fly), Tipula aino (a rice fly), Phormia regina (a black fly), Culex tritaeniorhynchus (a three-spotted mosquito), Anopheles sinensis (a malaria mosquito), Hylemya brassicae (a cabbage fly), and Asphondylia sp. (a soybean leaf beetle).European flower fly (Delia platura), onion seed fly (Delia antiqua), European cherry fruit fly (Rhagoletis cerasi), underground house mosquito (Culex pipiens molestus Forskal), Mediterranean fruit fly (Ceratitis capitata), small black-winged hair fly (Bradysia agrestis), beet leafminer (Pegomya cunicularia), tomato leafminer (Liriomyza sativae), tomato leafminer (Liriomyza bryoniae), pea leafminer (Chromatomyia horticola), onion leafminer (Liriomyza chinensis), Culex quinquefasciatus, Aedes aegypti, Aedes albopictus, gerbera leafminer (Liriomyza trifolii), tomato leafminer (Liriomyza sativae), oriental fruit fly (Dacus dorsalis), mandarin orange fruit fly (Dacus Examples include *Tsuneonis*, wheat midge (*Sitodiplosis mosellana*), black-bellied wheat stem fly (*Meromuza nigriventris*), Mexican fruit fly (*Anastrepha ludens*), and apple fruit fly (*Rhagoletis pomonella*).

[0151] As diseases of the Hymenoptera (Apiformes), examples include two-needle ants (Pristomyrmex pungens), ant-like bees, pharaoh ants (Monomorium pharaohnis), broad-segmented big-headed ants (Pheidole noda), red cabbage leaf bees (Athalia rosae), chestnut gall bees (Dryocosmus kuriphilus), Japanese mountain ants (Formica fusca japonica), wasps (Vespinae, Wasp), yellow-tailed bumblebees (Athalia infumata infumata), rose leaf bees (Arge pagana), turnip leaf bees (Athalia japonica), leafcutter ants (Acromyrmex spp.), red imported fire ants (Solenopsis spp.), apple leaf bees (Arge mali), and smooth tube glass ants (Ochetellus glaber), etc.

[0152] As diseases of the order Orthoptera (grasshoppers), examples include grasshoppers (Homorocoryphus lineosus), mole crickets (Gryllotalpa sp.), small rice grasshoppers (Oxya hyla intricata), small-winged rice grasshoppers (Oxya yezoensis), migratory grasshoppers (Locusta migratoria), Japanese rice grasshoppers (Oxya japonica), dwarf grasshoppers (Homorocoryphus jezoensis), and yellow-faced oil crickets (Teleogryllus emma), etc.

[0153] As diseases of the order Thysanoptera, examples include: red-banded thrips (Selenothrips rubrocinctus), rice thrips (Stenchaetothrips biformis), rice tube thrips (Haplothrips aculeatus), persimmon tube thrips (Ponticulothrips diospyrosi), pale thrips (Thrips flavus), yellow thrips (Anaphothrips obscurus), camphor tube thrips (Liothrips floridensis), gladiolus thrips (Thrips simplex), chrysanthemum brown-spotted thrips (Thrips nigropilosus), croton thrips (Heliothrips haemorrhoidalis), mulberry thrips (Pseudodendrothrips mori), chrysanthemum thrips (Microcephalothrips abdominalis), pine long-tailed tube thrips (Leeuwenia pasanii), and pine round tube thrips (Litotetothrips). pasaniae), Citrus thrips (Scirtothrips citri), Chinese thrips (Haplothrips chinensis), Soybean thrips (Mycterothrips glycines), Japanese tobacco thrips (Thrips setosus), Small yellow thrips (Scirtothrips dorsalis), Tea stick thrips (Dendrothrips minowai), Grass tube thrips (Haplothrips niger), Onion thrips (Thrips tabaci), Green onion thrips (Thrips alliorum), Flower thrips (Thrips hawaiiensis), Flower tube thrips (Haplothrips kurdjumovi), Mang thrips (Chirothrips manicatus), Taiwan flower thrips (Frankliniella intonsa), Colored thrips (Thrips coloratus), Western flower thrips (Franklinella occidentalis), Southern yellow thrips (Thrips palmi), Lily yellow thrips (Frankliniella) Lilivora and Lily Thrips vaneeckei, etc.

[0154] As diseases caused by mites, examples 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*, *Phyllocoptruta citri*, *Aculus schlechtendali*, and *Panonychus schlechtendali*. ulmi), as well as Rhyzoglyphus robini, and a species of the genus Sancassania sp., etc.

[0155] As a termite disease, examples include *Reticulitermes miyatakei*, *Incisitermes minor*, *Coptotermes formosanus*, *Hodotermopsis japonica*, *Reticulitermes sp.*, *Reticulitermes flaviceps amamianus*, *Glyptotermes kushimensis*, *Coptotermes guangzhoensis*, *Neotermes koshunensis*, *Glyptotermes kodamai*, *Glyptotermes satsumensis*, *Cryptotermes domesticus*, *Odontotermes formosanus*, and *Glyptotermes formosanus*. Termites such as *Nakajimai*, *Pericapritermes nitobei*, and *Reticulitermes speratus*.

[0156] As diseases of the order Blattodea, examples include the black-brown cockroach (Periplaneta fuliginosa), the German cockroach (Blattella germanica), the oriental cockroach (Blatta orientalis), the brown cockroach (Periplaneta brunnea), the German cockroach (Blattella lituricollis), the Japanese cockroach (Periplaneta japonica), and the American cockroach (Periplaneta americana).

[0157] As nematodes, examples include strawberry nematode (Nothotylenchus acris), rice root nematode (Aphelenchoides besseyi), northern root rot nematode (Pratylenchus penetrans), northern root nodule nematode (Meloidogyne hapla), sweet potato root nodule nematode (Meloidogyne incognita), golden nematode (Globodera rostochiensis), Javan root nodule nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), southern root rot nematode (Pratylenchus coffeae), wheat root rot nematode (Pratylenchus neglectus), and citrus nematode (Tylenchus semipenetrans).

[0158] As a class of mollusks, examples include the golden apple snail (Pomacea canaliculata), the African giant snail (Achatina fulica), the slug (Meghimatium bilineatum), the Valencian slug (Lehmannina valentiana), the yellow slug (Limax flavus), and the flat snail (Acusta despecta sieboldiana).

[0159] Furthermore, the fungicide for agricultural and horticultural use of the present invention also has a strong insecticidal effect on the tomato leafminer (Tuta absoluta), which is another disease.

[0160] The fungicide for agricultural and horticultural use, which is based on the compound of general formula [I] or its salts as the active ingredient, has a significant control effect on the aforementioned diseases that cause damage to paddy field crops, farmland crops, fruit trees, vegetables, other crops, and flowers. Therefore, it can be used in conjunction with the disease occurrence prediction period to treat seedling facilities, paddy fields, farmland, fruit trees, vegetables, other crops, flowers, seeds, paddy field water, stems and leaves, or soil and other cultivation carriers before the disease occurs or when it is confirmed to have occurred, thereby achieving the desired effect of the fungicide for agricultural and horticultural use of the present invention. By treating the seedling soil, transplanting hole soil, plant roots, irrigation water, and cultivation water in hydroponics of crops and flowers, the compound of the present invention can be absorbed by the roots through or without penetrating the soil, or it can be applied by osmotic transfer.

[0161] There are no particular limitations on the useful plants for which the fungicide of the present invention can be used, such as grains (e.g., rice, barley, wheat, rye, oats, corn, etc.), legumes (soybeans, red 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 and fruits (cabbage, tomatoes, spinach, broccoli, lettuce, onions, scallions (wild onions, yellow onions), green peppers, eggplants, strawberries, peppers, okra, leeks, etc.), and root vegetables (carrots, potatoes, sweet potatoes, taro, radishes, turnips, lotus roots, burdock, etc.). Garlic, buckwheat, etc.), processing crops (cotton, hemp, beets, hops, sugarcane, olives, rubber, coffee, tobacco, tea, etc.), cucurbitaceae (pumpkin, cucumber, watermelon, cantaloupe, honeydew melon, etc.), forage grasses (duckgrass, sorghum, cat's tail grass, clover, alfalfa, etc.), turf crops (Korean grass, small bran grass, etc.), spices and ornamental crops (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemum, rose, carnation, orchid, tulip, lily, etc.), garden trees (ginkgo, cherry trees, cedar, etc.), forest trees (Sakhalin fir, spruce, pine, cypress, fir, juniper, eucalyptus, etc.), and other plants.

[0162] The above-mentioned "plants" also include plants that have been conferred herbicide resistance through traditional breeding methods or gene recombination technology. Such herbicides include, for example, HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazapyr and thifensulfuron methyl, EPSP synthase inhibitors such as glyphosate, glutamic acid synthase inhibitors such as glufosinate, acetyl-CoA carboxylase inhibitors such as sethoxydim, bromobenzonitrile, dicamba, 2,4-D, etc.

[0163] Examples of "plants" that have been conferred resistance through traditional breeding methods include rapeseed, wheat, sunflower, and rice, which possess resistance to imidazolidinone-based ALS-inhibiting herbicides such as etorizine. Rice is already commercially available under the trade name Clearfield (registered trademark). Similarly, soybeans, which have been conferred resistance to sulfonylurea-based ALS-inhibiting herbicides such as thifensulfuron-methyl through traditional breeding methods, are already commercially available under the trade name STS soybean. Likewise, plants that have been conferred resistance to acetyl-CoA carboxylase inhibitors such as triketoxime and aryloxyphenoxypropionic acid herbicides through traditional breeding methods include SR corn. Furthermore, plants resistant to acetyl-CoA carboxylase inhibitors are documented 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), etc. Furthermore, a mutant acetyl-CoA carboxylase resistant to acetyl-CoA carboxylase inhibitors was disclosed in Weed Science, Vol. 53, pp. 728-746 (2005). By introducing this mutant acetyl-CoA carboxylase gene into plants using gene recombination technology, or by introducing resistance-related mutations into plant acetyl-CoA carboxylase, plants resistant to acetyl-CoA carboxylase inhibitors can be produced. Additionally, using chimeraplasty technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.), a base substitution mutation is introduced into nucleic acids into plant cells, and specific amino acid substitution mutations are made at the insertion sites of the plant's acetyl-CoA carboxylase gene or ALS gene. This allows the production of plants resistant to acetyl-CoA carboxylase inhibitors or ALS inhibitors, and the fungicide of this invention can also be used on such plants.

[0164] Further, examples of toxins expressed in recombinant plants include insecticidal proteins derived from *Bacillus cereus* or *Bacillus japonicus*; δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, insecticidal proteins such as VIP1, VIP2, VIP3, or VIP3A derived from *Bacillus thuringiensis*; insecticidal proteins derived from nematodes; toxins produced by animals such as scorpion venom, spider venom, bee venom, or insect-specific neurotoxins; filamentous fungal toxins; phytohemagglutinins; lectins; trypsin inhibitors; serine proteins. Enzyme inhibitors, including protease inhibitors such as patatin, cystin, and papain inhibitor; ribosomal inactive proteins (RIPs) such as ricin, maize-RIP, abrin, fentanyl, saporin, and bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysone-UDP-glycosyltransferase, and cholesterol oxidase; ecdysone inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone containment bodies; succinate synthase; bibenzyl synthase; chitinase; and polyglucanase.

[0165] Furthermore, the toxins expressed by the genetically recombinant plants in this manner include hybrid toxins, partially deficient 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 by recombinating dissimilar regions of these proteins using recombinant technology. Partially deficient toxins are known to include Cry1Ab with partially missing amino acid sequences. Modified toxins are amino acids that replace one or more naturally occurring toxins. Examples of such toxins and recombinant plant lines capable of synthesizing such toxins are recorded in EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878, WO03 / 052073, etc.

[0166] The toxins contained in these recombinant plants can, in particular, confer resistance to diseases of beetles, hemiptera, dipterans, lepidopterans, and nematodes. The agro-horticultural fungicide of the present invention can be used in conjunction with or systematically with these technologies.

[0167] To prevent and control various diseases, the agricultural and horticultural fungicide of the present invention can be applied directly, appropriately diluted with water, or in suspension to plants predicted to be susceptible to the disease in an effective amount for disease control. For example, it can be applied to the stems and leaves for diseases occurring in fruit trees, grains, and vegetables. Furthermore, it can be applied to the soil through seed soaking, seed coating, Calper treatment, soil mixing, furrow application, bed soil mixing, seedling treatment, planting hole treatment, root fertilization, rice seedling treatment, or surface application, and absorbed through the roots. Additionally, it can be applied to the soil in hydroponic cultivation, through fumigation, or by injecting into the trunk. Furthermore, the agricultural and horticultural fungicide of the present invention can be applied directly, appropriately diluted with water, or in suspension form to the site where the disease is predicted to occur, in an effective amount for disease control. Examples include applications to stored grain diseases, house diseases, sanitary diseases, and forest diseases. It can also be applied to building materials, used as fumigation, or as bait. Furthermore, the agricultural and horticultural fungicide of the present invention can be applied directly, appropriately diluted with water, or in suspension form to the site where the disease is predicted to occur, in an effective amount for disease control.

[0168] Seed treatment methods may include, for example, methods of forming a liquid or solid preparation into a liquid state with dilution or undilution and impregnating the seeds to allow the agent to penetrate; methods of mixing a solid or liquid preparation with the seeds and applying a powder coating to adhere to the seed surface; methods of mixing with an adhesive carrier such as resin or polymer and coating the seeds; and methods of dispersing near the seeds during planting. The "seed" used for this seed treatment refers to the plant body used in the early stages of cultivation for plant propagation. In addition to seeds, examples include, for example, bulbs, tubers, seed potatoes, buds, propagules, bulbs, or plant bodies used for vegetative propagation through cuttings. When implementing the method of use of this invention, the "soil" or "cultivation carrier" of the plant refers to the support used to cultivate the crop, especially the support for root growth. There are no particular restrictions on the material, as long as it is a material that the plant can grow on, such as soil, seedling mat, water, etc. Specific materials may include sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, polymers, rock wool, glass wool, wood chips, bark, etc.

[0169] Methods for distributing to the stems and leaves of crops include distributing liquid preparations such as emulsions and flow agents, or solid preparations such as hydrating agents or granular hydrating agents, appropriately diluted with water; distributing powders; or fumigation. Methods for applying to the soil include, for example, applying liquid preparations to the roots of plants or seedbeds with or without water; distributing granules to the roots of plants or seedbeds; distributing powders, hydrating agents, granular hydrating agents, or granules before sowing or transplanting and mixing them with the soil; planting in holes before sowing or planting plants; and distributing powders, hydrating agents, granular hydrating agents, or granules in furrows.

[0170] Regarding the application method for rice seedling trays, the formulation may vary depending on the application time, such as application at sowing, application during the greening period, or application at transplanting, but powder, granular hydrate, or granule formulations are generally acceptable. It can also be applied by mixing with hilling soil, such as mixing with seedbed soil, covering soil, or mixing with hilling soil as a whole. Alternatively, hilling soil can be layered with various formulations and applied. Regarding the application method for paddy fields, solid formulations such as large granules, packaged formulations, granules, and granular hydrates, as well as liquid formulations such as flowable agents and emulsions, can generally be dispersed in the flooded paddy field. Furthermore, appropriate formulations can be injected directly or mixed with fertilizer and dispersed into the soil during transplanting. Also, emulsions and flowable agents can be applied at the source of water flowing into the paddy field, such as at water inlets or irrigation devices, allowing for labor-saving application along with the water supply.

[0171] In agricultural crops, during the period from sowing to seedling stage, the seeds or the cultivation medium next to the plant can be treated. For plants directly sown in agricultural land, in addition to direct seed treatment, it is preferable to treat the roots of the cultivated plant. Granules can be used for dispersal, or the agent can be diluted with water or undiluted to form a liquid for irrigation. A preferred treatment is to mix the granules with the cultivation medium before sowing. For transplanted cultivated plants, in addition to direct seed treatment, it is preferable to irrigate the seedbed with a liquid agent or disperse granules. Furthermore, a preferred treatment is to treat the planting hole with granules at transplanting or mix with the cultivation medium near the transplanting site. The agricultural and horticultural fungicide of the present invention is generally formulated into an easy-to-use form according to conventional methods of pesticide formulation. That is, the compound or its salts represented by the general formula [1] of the present invention can be mixed with appropriate carriers and dissolved, separated, suspended, mixed, impregnated, adsorbed or attached, and the preparation is in an appropriate dosage form, such as a suspension, emulsion, liquid, hydration agent, granular hydration agent, granule, powder, tablet, packaged, etc.

[0172] The fungicide composition for agricultural and horticultural use 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, thickeners, colorants, spreaders, stratifying agents, antifreeze agents, anti-caking agents, disintegrating agents, and decomposition inhibitors. Furthermore, preservatives, plant flakes, and other additives may be used as needed. These additives may be used alone or in combination of two or more.

[0173] As solid carriers, examples include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, magnesium aluminum sepiolite, 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 shell, corn cob, tobacco stems, etc.); plastic carriers such as polyethylene, polypropylene, and polyvinylidene chloride; urea, inorganic hollow materials, plastic hollow materials, and fumed silica (white carbon). These can be used alone or in combination of two or more.

[0174] As a liquid carrier, examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexanediol, polyethylene glycol, polypropylene glycol, and glycerol; polyhydric alcohol compounds such as propylene glycol ethers; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; chain or cyclic ethers such as ethyl ethers, dioxane, ethylene glycol monoethyl ether, dipropyl ether, and tetrahydrofuran; and aliphatic hydrocarbons such as n-alkanes, cycloalkanes, isoalkanes, kerosene, and mineral oil. Aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, and alkylnaphthalene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate; lactones such as γ-butyrolactone; acetamides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidone, 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. Furthermore, these substances can be used alone or in combination of two or more.

[0175] Examples of surfactants used as dispersants or wetting agents include, for example, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin esters, polyoxyethylene fatty acid diesters, polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene nonylphenyl ethers, polyoxyethylene dialkylphenyl ethers, polyoxyethylene alkylphenyl ether formalin condensates, polyoxyethylene polyoxypropylene block copolymers, polystyrene polyoxyethylene block copolymers, alkyl polyoxyethylene polypropylene block copolymer ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amines, polyoxyethylene fatty acid diphenyl ethers, polyalkylbenzylphenyl ethers, polyoxyalkyl alkylstyrene phenyl ethers, acetylenide glycol, polyoxyalkyl addition acetylenide glycol, polyoxyethylene ether-type polysiloxane, ester-type polysiloxane, fluorinated surfactants, polyoxyethylene castor oil, and polyoxyethylene... Nonionic surfactants such as hydrogenated castor oil of ethylene; cationic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkylphenyl ether sulfates, polyoxyethylene styrene phenyl ether sulfates, alkylbenzene sulfonates, alkylaryl sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, formalin condensate salts of naphthalene sulfonic acid, formalin condensate salts of alkylnaphthalene sulfonic acid, fatty acid salts, polycarboxylate salts, polyacrylates, N-methyl-fatty acid sarcosinates, resin salts, polyoxyethylene alkyl ether phosphates, and polyoxyethylene alkylphenyl ether phosphates; cationic surfactants such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylamine propylamine acetate, alkyltrimethylammonium chloride, and alkyldimethylbenzylammonium chloride; and amphoteric surfactants such as amino acid-type or betaine-type surfactants. These surfactants can be used alone or in combination of two or more.

[0176] As binders or adhesives, examples include carboxymethyl cellulose or its salts, dextrin, water-soluble starch, gum arabic, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol with an average molecular weight of 6,000 to 20,000, polyethylene oxide with an average molecular weight of 100,000 to 5,000,000, phospholipids (e.g., cephalin, lecithin, etc.) cellulose powder, dextrin, processed starch, polyamine carboxylic acid chelate compounds, cross-linked polyvinylpyrrolidone, copolymers of maleic acid and styrene, (meth)acrylic acid copolymers, half-esters of polymers composed of polyols and dicarboxylic anhydrides, water-soluble salts of polystyrene sulfonic acid, paraffin wax, terpenes, polyamide resins, polyacrylates, polyoxyethylene, waxes, polyethylene alkyl ethers, alkylphenol formalin condensates, synthetic resin emulsions, etc.

[0177] As a thickener, examples include guar gum, diutan gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds, water-soluble polymers such as polysaccharides, high-purity bentonite, inorganic micro powders such as fumed silica, etc.

[0178] Examples of coloring agents include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue; and organic dyes such as alizarin dyes, azo dyes, and metallic phthalocyanine dyes.

[0179] As antifreeze agents, examples include polyols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

[0180] Examples of adjuvants that promote anti-caking or 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 stearate, cellulose powder, dextrin, methacrylate copolymers, polyvinylpyrrolidone, polyamine carboxylic acid chelate compounds, styrene / isobutylene / maleic anhydride copolymers, starch / polyacrylonitrile graft copolymers, etc.

[0181] Examples of decomposition prevention agents include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenolic compounds, amine compounds, sulfur compounds, and phosphoric acid compounds; and ultraviolet absorbers such as salicylic acid compounds and diphenyl ketone compounds.

[0182] Examples of preservatives include potassium sorbate and 1,2-benzothiazolin-3-one. Further, depending on the requirements, functional spreading agents, metabolic decomposition inhibitors such as piperine butyrate, antifreeze agents such as propylene glycol, antioxidants such as BHT, and other excipients such as ultraviolet absorbers may be used.

[0183] The blending ratio of the active ingredient compound can be increased or decreased as needed. It can be appropriately selected from 0.01 to 90 parts by weight in 100 parts by weight of the fungicide for agricultural and horticultural use in this invention. For example, when it is a powder, granule, emulsion or hydration agent, it is more appropriate to use 0.01 to 50 parts by weight (0.01 to 50 parts by weight relative to the total weight of the fungicide for agricultural and horticultural use).

[0184] The dosage of the fungicide for agricultural and horticultural use in this invention may vary depending on various factors, such as the purpose, the disease status of the target crop, the crop growth status, the tendency of disease occurrence, weather, environmental conditions, formulation, application method, application site, and application period. The active ingredient compound may be appropriately selected in the range of 0.001g to 10kg per 10 acres, preferably 0.01g to 1kg, depending on the purpose.

[0185] The fungicide for agricultural and horticultural use of the present invention can be used in combination with other fungicides, acaricides, nematicides, fungicides, biological pesticides, etc., for the purpose of expanding the scope of pests and diseases to be controlled, the duration of control, or reducing the dosage. It can also be used in combination with herbicides, plant growth regulators, fertilizers, etc., depending on the application.

[0186] Other agricultural and horticultural fungicides, acaricides, and nematicides used for this purpose include, for example, 3,5-xylyl methylcarbamate (XMC), Bacillus thuringienses (e.g., Bacillus thuringienses aizawa, Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses kurstaki, and Bacillus thuringienses subsp. kurstaki). Crystalline protein toxins produced by *Tenebrionis*, etc., BPMC (N-methylaminocarbamate-2-(1-methylpropyl)phenyl ester), Bt toxin-based insecticidal compounds, chlorfenson (CPCBS), dichlorodiisopropyl ether (DCIP), 1,3-dichloropropene (DD), DDT, NAC, O-4-dimethylaminesulfonylphenyl O,O-diethyl phosphorothioate (DSP), O-ethyl-O-4-nitrophenyl phenyl thiophosphate (DSP) phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, acynonapyr, azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, abamectin, afidopyropen, avermectin-B, amidoflumet, amitraz, alanycarb, aldicarb, aldoxycarb, aldrinAlpha-endosulfan, alpha-cypermethrin, alpha-bromadiolone, albendazole, allethrin, isazofos, isamidofos, isoxathion, isocycloseram The following are listed as examples of pesticides: isofenphos, isoflurane, isoprocarb (MIPC), epsilon-metofluthrin, epsilon-momfluorothrin, ivermectin, imicaefos, imidacloprid, imiprothrin, indoxacarb, esfenvalerate, ethiofencarb, ethion, etiprole, etoxazole, ethofenprox, etrimfos, emamectin, emamectin-benzoate, endosulfan, empenthrin, and 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, chinomethionatGlycerol citric acid fatty acid ester, glycerol fatty acid ester, glycerol acetic acid fatty acid ester ester), cloethocarb, clothinin, clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyfos, chlordimeform, chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr, chlorfenson, chlorfenvinphos, chlorfluazuron, chlorobenzilate, chloroprallethrin, chlorobenzoate, dicofol, salithion, cyanophos (CYAP), diafenthiuron, diamidafo s), cyantraniliprole, theta-cypermethrin, cyetpyrafen, dienochlor, cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin, cyclaniliprole, dichlofenthion (ECP), cyclobutrifluram, cycloprothrin, dichlorvos (DDVP), diloromezotiaz, disulfoton, dinotefuran, cyhalodiamide, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron, cyflumetofendiflovidazin, cyproflanilide, cyhexatin, cypermethrin, cybenzoxasulfyl, dimpropyridaz, dimethylvinphos, dimethoate, dimefluthrin, silafluofen, cyromazine, spidoxamat, and spine toram, spinosad, spirodiclofen, spirotetramat, spiropidion, spirobudifen, spiromesifen, sulfiflumin, sulfluramid, sulprofos, sulfoxaflor, sulfoxamyl, zeta-cypermethrin, sorbitan fatty acid ester), diazinon, tau-fluvalinate, dazomet, thiacloprid, tiapyrachlor, thiamethoxam, tioxazafen, thiodicarb, thiocyclam, thiosultap, thiosultap-sodium, thionazin, thiometon, tiorantraniliprole Tyclopyrazoflor, deet, dieldrin, tetrachlorantraniliprole, tetrachlorvinphos, tetradifon, tetraliprole, tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrinTeflubenzuron, Demeton-S-methyl, Temephos, Deltamethrin, Terbufos, Doramectin, Tralopyril, Tralomethrin, Transfluthrin, Triazamate, Triazuron, Trioxyflanilide, Trichlam ide), trichlorphon (DEP), triflumuron, triflumezopyrim, tolfenpyrad, naled (BRP), nicofluprole, nithiazine, nitenpyram, novaluron, noviflumuron, hydroprene, vadescana / GreenLight Biosciences, vaniliprole, vamidothion, parathion, parathion-methyl, halfenprox, halofenozide, pioxaliprole, bistrifluron, bisultap, bisulflufen, hydramethylnon, hydroxypropyl starch, hydroxypropyl starch solution Solution, binapacryl, vinylfluthrin, bifenazate, bifenthrin, pyflubumide, piperflanilide, pymetrozine, pyraclorfos, pirafluprole, pyridafenthion, pyridaben, pyridalyl, pyrifluquinazon, pyriprolePyriproxyfen, Pirimicarb, Pyrimidifen, Pyriminostrobin, Pirimiphos-methyl, Pyrethrins, Fipronil, Fenazaquin, Fenamiphos, Phenisobromolate, Fenitrothion (MEP), Fenoxycarb, Fenthiocarb othiocarb, phenothrin, fenobucarb, fensulfothion, fenthion (MPP), phenthoate (PAP), fenvalerate, fenpyroximate, fenpropathrin, fenbendazole, fosthiazate, formetanate, butathiofos Buprofezin, fluazaindolizine, furathiocarb, prallethrin, fluacrypyrim, fluazinam, fluazuron, fluensulfone, fluxametamide, flucycloxuron, flucythrinate, fluvalinate, flupyradifurone, flupyrazofos, flupyrimidine Yrimin, flupyroxystrobin, flufiprole, flufenerim, flufenoxystrobin, flufenoxuron, flufenzine, flufenoprox, fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flupentiofenox, flumetnicam, and flumethrin.Flurimfen, Prothiofos, Protrifenbute, Flunicamid, Propaphos, Proargite (BPPS), Propylene glycol mono fatty acid ester, Profenofos, Broflanilide, Profluthrin, Prooxur (PHC), Flometoquin, Bromopropylate, Beta-cyfluthrin, Hexaflumuron, Hexythiazox, Heptafluthrin, Heeptenophos, Permethrin, Benclothiaz, and Miconazole Bendiocalb, benzpyrimoxan, bensultap, benzoximate, bentioflumin, benfuracarb, phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet (PMP), polyoxyethylene sorbitan fatty acid ester (The list of ingredients is incomplete and contains several typologies. A direct translation wouldn't be meaningful without further context.)Methomethyl, metaldehyde, metaflumizone, methamidophos, metam-ammonium, metam-sodium, methiocarb, methidathion (DMTP), methylisothiocyanate, methylneodecanamide, methylparathion, metoxadiazone, methoxychlor, methoxyfenozide, metofluthrin, methoprene, metolcarb, mevinphos, meperfluthrin, monocrotophos, monosultap, momfluorothrin, 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, cyhexatin, calcium cyanamide, calcium polysulfide, suffoil, machine oil (a physical repellent), sulfur, nicotine sulfate, etc.

[0187] Agricultural and horticultural fungicides used for the same purpose include, for example, aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, aminotipyr, ampropylfos, metoctradin, and allyl alcohol. alcohol), aldimorph, amobam, isotianil, isovaledione, isopyrazam, isofetamid, isoflucypram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin, iprodione, iprovalicarb, iprobenfos, imozalil, iminoctadine, iminoctadine-albesilate, iminoctadine-triacetate, iminoctadine-triacetate, iminoctadine-albesil ... ibenconazole, uniconazole, uniconazole-P, echlomezole, edifenphos, etaconazole, ethaboxam, ethirimol, etem, ethoxyquin, etridiazole, enestroburin, enoxastrobin, epoxiconazole, oxadixyl, oxycarboxin, oxathiapiprolin, copper-8-quinolinolate, oxytetracycline, copper-oxinate.Oxpoconazole, oxpoconazole-fumarate, oxolinic acid acid), octhilinone, ofuronide, orysastrobin, carbam (metam-sodium), kasugamycin, galquin / silvateam, carbamorph, carpropamid, carbendazim, carboxin, carvone, quinazamid, quinacetol, quinaminoprole, quinoxyfen, quinofumelin, quinomethionate, captafol, captan, kiralaxyl, quinconazole, quintozene, guazatine, cufraneb, cu... Probam, Coumoxystrobin, Glyoydin, Griseofulvin, Climbazole, Cresol, Kresoxim-methyl, Chlozolinate, Clotrimazole, Chlobenthiazone, Chloraniformethan, Chloranil, Chlorquinox, Chlorpicrin, Chlorfenazole, Chlorinconazide, Chlordinitronaphthalene, Chlorthalonil, Chlorneb, Zarilamid, Salicylanilide, Cyazofamid, Diethyl pyrocarbonate pyrocarbonate, diethofencarb, cyclafuramid, diclocymet, dichlozolineDiclobutrazol, dichlofluanid, cycloheximide, dichlobentiazox, diclomezine, dicloran, dichlorophen, dichlone, disulfiram, ditalimfos, dithianon, diniconazole, diniconazole-M, zineb, dinocap, dinocto n), nitroglycerin (dinosulfon), nitrobutyl ester (dinoterbon), dinobuton, dinopenton, dipymetitrone, dipyrithione, diphenylamine, difenoconazole, cyflufenamid, diflumetorim, cyproconazole, cyprodinil, cyprofuram, cypendazole, simeconazole, dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, methyl bromide bromide, ziram, silthiofam, streptomycin, spiroxamine, sultropen, sedaxane, seboctylamine, zoxamide, dazomet, thiadiazin, tiadinil, thiadifluor, thiabendazole, tioxymid, thiochlorfenphim, thiophanate, thiophanate-methyl, thicyofen, thioquinox, chinomethionat, thifluzamide, thiramDecafentin, Tetrachloronitrobenzene, Tecloftalam, Tecoram, Tetraconazole, Debacarb, Dehydroacetic acid acid), tebuconazole, tebufloquin, dodicin, dodine, diethylenediamine copper sulfonate (II) (DBEDC), dodemorph, drazoxolon, triadimenol, triadimefon, triazbutil, triazoxide, triamiphos, triarimol, trihlamide, trilopyricarb, tricyclazole, triticonazole, tridridemorph, tributyltin oxide), triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolprocarb, natamycin, nabam, nitrothal-isopropyl, nitrostyrene, nuarimol, copper nonylphenol sulfonate, halacrinate, validamycin, valifenalate, harpin Protein, picarbrazox, bixafen, picoxystrobin, picobenzamide, pydiflumetofen, bithionol, bitertanol, hydroxyisoxazole, hydroisoxazole-potassium, binapacryl, biphenylPiperalin, Hymexazol, Pyraoxystrobin, Pyracarbolid, Pyraclostrobin, Pyrazophos, Pyrametostrobin, Pyriofenone, Pyridinitril, Pyrisoxazole, Pyridachlometyl, Pyrifenox, Pyribencarb, Pyrifenamide (pyriminostrobin), pyrimethanil, pyroxychlor, pyroxyfur, pyroquilon, vinclozolin, ferbam, famoxadone, fenapanil, fenamidone, fenaminosulf, fenaminstrobin, fenarimol, finitropan, quinclorac eptamidoquin, fenoxanil, fenopyramid, ferimzone, ferbam, fentin, fenpiclonil, fenpicoxamid, fenpyrazamine, fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid, phtha (The following are listed as examples of fungicides): lide, buthiobate, butylamine, bupirimate, fuberidazole, blasticidin-S, furametpyr, furalaxyl, fluacrypyrim, fluazinam, fluindapyr, fluoxastrobin, fluoxapiprolin, fluoxytioconazole, fluotrimazole, fluopicolide.Fluopimomide, fluopyram, fluoroimide, furcarbanil, fluxapyroxad, fluquinometoate, fluquinconazole, furconazole, furconazole-cis, fludioxonil, flusilazole, flusulfamide Flutianil, flutolanil, flutriafol, flufenoxadiazam, flufenoxystrobin, furfural, flubeneteram, furmecyclox, flumetylsulforim, flumetover, flumorph, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole, propamocarb, pronitridine, propiconazole, propineb, furophanate, probenazole, bromuconazole, florylpicoxamid, hexachlorob Utadiene), hexaconazole, hexylthiofos, bethoxazin, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, benquinox, penconazole, benzamorf, pencycuron, benzohydroxamic acid, benzovindiflupyr, bentaluron, benthiazole, benthiavalicarbBenthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, phosdiphen, fosetyl, fosetyl-aluminum, polyoxins, polyoxorim, polycarbamate, folpet, formaldehyde, machine oil oil), maneb, mancozeb, mandipropamid, mandestrobin, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid, metasulfocarb, metazoxolon, metam, metam-sodium, metalaxyl, metalaxyl-M, metarylpicoxamid, metiram, methyl isothiocyanate Inorganic fungicides such as isothiocyanate, metyltetraprole, mepthyldinocap, metyltetraprole, metconazole, metsulfovax, methfuroxam, metominostrobin, metrafenone, mepanipyrim, mefenoxam, mefentrifluconazole, meptyldinocap, mepronil, mebenil, iodomethane, rabeprazole, benzalkonium chloride, basic copper chloride, basic copper sulfate, and silver; sodium hypochlorite and copper hydroxide.Hydrated sulfur, calcium polysulfide, potassium hydrogen carbonate, sodium hydrogen carbonate, inorganic sulfur, anhydrous copper sulfate, nickel dimethyldithiocarbamate, copper-based compounds such as oxine copper, zinc sulfate, and copper sulfate pentahydrate, etc.

[0188] Similarly, examples of herbicides include 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, thioethyl MCPA, MCPB, ioxynil, aclonifen, and other herbicides. Azafenidin, acifluorfen, aziprotryne, azimsulfuron, asulam, acetochlor, atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid acid), amicabazone, amidosulfuron, amitrol, aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridone, ametryn, alachlor, allidochlor, alloxydim, alarac, iofensulfuron, icafolin, isouron, isocarbamid, isoxachl ortole, isoxapyrifop, isoxafenacil, isoxaflutole, isoxaben, isoxacin, isoruron, isopreturon, isopropalin, isopolinate, isomethiozin, inabenfide, ipazine, iptriazopyrid, ipfencarbazone, iprymidam, imazaquin, imazapic, imazapyrImazamethapyr, imazamethabenz, imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolebutyric acid, indolauxipyr, indolauxipyr-cyanomethyl, uniconazole-P, eglinazine, esprocarb, ethametsulfuron, ethametsulfuron-methyl, etalfluralin, ethiolate, ethychlozate-ethyl, ethidimuron, etinofen, ethephon, ethoxysulfuron, ethoxyfen, etnipromid, ethofumesate, etobenzanid, epyrifenacil, epronaz, erbon, cotton defoliant ( Endothal, oxadiazon, oxadiargyl, oxaziclomefone, oxasulfuron, oxapyrazon, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb, cafenstrole, cambendichlor, carbasulam, carfentrazone, carfentrazone-ethyl, karbutilate, carbetamide, carboxazole, quizalofop, quizalofop-P, quizalofop-ethyl, xylachlor, quinoclamineQuinonamid, quinclorac, quinmerac, cumyluron, clacyfos, cliodinate, glyphosate, glufosinate, glufosinate-P, credazine, clethodim, cloxyfonac, clodinafop, clodinafop-propargyl, chlorotyl... oluron, clopyralid, cloproxydim, cloprop, chlorbromuron, clofop, cromazine, chlomethoxynil, chlomethoxyfen, cromprop, chlorazifop, chlorazine, chloranocryl, chloramben, cloransulam 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, cypyrafluone, saflufenacil, cyanazine, cyanatrynDi-allate, diuron, diethamquat, dioxopyritrione, dicamba, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron, cyclopyranil Cyclopyrimorate, dichlorprop, dichlorprop-P, dichlobenil, dichlobenz-methyl, diclofop, diclofop-methyl, dichlormate, dichloralurea, diquat, cisanilide, disul, siduron, dithiopyr, diinitramine, cinidon-ethyl, dinosam, cinosulfuron, dinoseb, dinoterb, dinofenate, dinoprop, cyhalofop-butyl, and dafen. Diphenamid, difenoxuron, difenopenten, difenzoquat, cybutryne, cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn, cypromid, cyperquat, gibberellin, simazine, dimexano, dimesulfazet, dimethachlor, dimidazon, dimethametryn, dimethenamid, simetryn, simeton, dimepiperate, dimepyrolimet.Dimefuron, cinflubrolin, cinmethylin, swep, sulglycapin, sulcotrione, sulfallate, sulfentrazone, sulfursulfuron, sulfometuron-methyl, secbumeton, sethoxydim, sebuthylazine Terbacil, Daimuron, Dazomet, Dalabon, Thiazafluron, Thiazopyr, Tiafenacil, Thiencarbazone, Thiencarbazone-methyl, Tiocarbazil, Tioclorim, Thiobencarb, Thiidiazimin, Thiidiazuron, Thifesulfonium nsulfuron, thifensulfuron-methyl, desmedipham, desmetryn, tetflupyrolimet, tetrafluron, thenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione, tembotrione, delachlor, etc. Terbacil, terbucarb, terbuchlor, terbuthylazine, terbutryn, toramezone, tralkoxydim, triaziflam, triasulfuron, triafamone, triallate, trietazine, tricamba, trilopyr, tridiphaneTritac, Tritosulfuron, Trifludimoxazin, Triflusulfuron, Triflusulfuron-methyl, Trifluralin, Trifloxysulfuron, Tripropindan, Tribenuron-methyl, Tribenuron, Trifop, T-fluorophosphate oxime rifopsime, trimeturon, tolpyralate, naptalam, naproanilide, napropamide, nicosulfuron, nitralin, nitrofen, nitrofluorfen, nipyraclofen, neburon, norflurazon, noruron, barban, paplobutr azol, paraquat, parafluron, haloxydine, halauxifen, haloxyfop, haloxyfop-P, haloxyfop-methyl, halosafen, halosulfuron, methyl halosulfuron, bilanafos, bixlozone, picloram, picolinafe n), bicyclopyrone, bispyribac, bispyribac-sodium, pydanon, pinoxaden, bipyrazone, bifenox, piperophos, hymexazol, pyraquinate, pyraclonil, pyrasulfotole, pyrazoxyfen, pyrazosulfuronPyrazosulfuron-ethyl, pyrazolate, bilanafos, piraflufen, ethyl piraflufen-ethyl, pyriclor, pyridafol, pyrithiobac, pyrithiobac-sodium, pyridate, pyriftalid, pyributicarb, pyriflubenzoxim ), pyribenzoxim, pyrimisulfan, primisulfuron, pyriminobac-methyl, pyroxasulfone, pyroxsulam, fenasulam, phenisopham, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, ethyl fenoxaprop ), Phenohiol, Fenoprop, Phenobenzuron, Feproxydim, Fenquinotrione, Fentiaprop, Fenteracol, Fentrazamide, Phenmedipham, Phenmedipham-ethyl, Fenpyrazone, Butachlor, Butafenacil, Butachlor (List of herbs follows: amifos, buthiuron, buthidazole, butylate, buturon, butenachlor, butroxydim, butralin, butroxydim, frazsulfuron, flamprop, furyloxyfen, prynachlor, primisulfuron-methyl, fluazifop)Fluazifop-P, butyl vortex fluazifop, fluazolate, fluchloraminopyr, flufenazopyr, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen, fluoromid Flucarbazone, flucarbazone-sodium, fluchloralin, flusulfinam, flucetosulfuron, flufenauxirim, flufenauxirim-metotyl, fluthiacet, fluthiacet-methyl, flupyrsulfuron, flufenacet, flufenpyrsulfuron Flufenican, flufenoximacil, flufenpyr, flupropacil, flupropanate, flupoxam, flumioxazin, flumiclorac, flumiclorac-pentyl, flumipropyn, flumezin, fluometuron, flumetsulam, fluridone The following herbicides are listed: flurtamone, fluroxypyr, pretilachlor, proxan, proglinazine, broclozone, prochlorosulfone, procyazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb, propaquizafop, and propachlor.Propazine, Propanil, Propyzamide, Proisochlor, Prohydrojasmon, Propyrisulfuron, Proham, Profluazol, Profluralin, Prohexadione-calcium, Prooxycarbazone, Prooxycarbazone-sodium, Cyclobutrazol profoxydim, bromacil, brompyrazon, prometryn, prometon, bromoxynil, bromofenoxim, bromobutide, bromobonil, florasulam, florpyrauxifen, hexachloroacetone, hexazinone, pethoxamid, benazo Lin), Penoxsulam, Pebulate, Beflubutamid, Beflubutamid-M, Vernolate, Perfluidone, Bencarbazone, Benquitrione, Benzadox, Benzipram, Benzylaminopurine, Benzthiazuron, Benzfendizone, Dimethoate ( Bensulide, bensulfuron-methyl, benzoylprop, benzobicyclon, benzofenap, benzofluor, bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate, fosamineflumethrin, foramsulfuron, forchlorfenuron, maleic acid hydrazide), mecoprop, mecoprop-P, medinoterb, mesosulfuron, mesosulfuron-methyl, mesotrione, mesoprazine, mesoprotryne, metazachlor, methazole, metazosulfuron, metabenzthiazuron, metamitron, metamifop, metam, mesalpropalin, metiuron, metiozolin, metiozolin bencarb, methyldymron, metoxuron, metosulam, metsulfuron-methyl, metflurazon, metproxybicyclone, metobromuron, metobenzuron, metometon, metolachlor, metribuzin, mepiquat-chloride, mefenacet, mefluidide, monalide, monisouron, mouron, monochloroacetic acid (The following are listed as herbicides and their related names: acid, monolinuron, molinate, morfamquat, iodosulfuron, iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactoferrin, lancotrione, rimisoxafen, linuron, rimsulfuron)Lenacil, rhodethanil, calcium peroxide, methyl bromide, etc.

[0189] Furthermore, the same effect can be expected by mixing with biological pesticides. Examples of biological pesticides include viral preparations such as nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), and entomopoxi virus (EPV); microbial pesticides such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, and Pasteuria penetrans, which are used as insecticides or nematicides; and non-pathogenic bacteria such as Trichoderma lignorum, Agrobacterium radiobactor, Erwinia carotovora, and Bacillus subtilis. Microbial pesticides such as *Xanthomonas campestris*, used as fungicides, and biological pesticides such as *Xanthomonas campestris*, used as herbicides, are used as fungicides.

[0190] Furthermore, it can be used in conjunction with biological pesticides, such as natural enemies including Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusa sibirica, Phytoseiulus persimilis, Amblyseius cucumeris, Orius sauteri, and Beauveria bassiana. Microbial pesticides such as brongniartii, and pheromones such as (Z)-10-tetradecenyl=acetate, (E,Z)-4,10-tetradecanediene=acetate, (Z)-8-dodecenyl=acetate, (Z)-11-tetradecenyl=acetate, (Z)-13-eicosene-10-one, and 14-methyl-1-dedecene.

[0191] Furthermore, as a biological pesticide, it may also be used with, for example, Agrobacterium spp. strains such as Agrobacterium radiobacter K84 (e.g., "Galltrol-A (registered trademark)" manufactured by "AgBioChem, CA"), Agrobacterium radiobacter K1026 (e.g., "Nogall (registered trademark)" manufactured by "Becker Underwood, US"), and Agrobacterium radiobacter strain 84 (e.g., "Bacterose (registered trademark)" manufactured by "Nippon Nippon Agricultural Chemicals Co., Ltd."); and Ampelomyces quisqualis strain AQ10 (e.g., "AQ 10 (registered trademark)" manufactured by "IntrachemBio Italia & Co.KG"). sp.); Aspergillus flavus (e.g., "Afla-Guard" manufactured by Syngenta (registered trademark)), Aspergillus flavus strain AF36 (e.g., "AF36" manufactured by Arizona Cotton Research and Protection Council, US (registered trademark)) and other Aspergillus spp.; Aureobasidium spp., a mixture of budding spores of Aureobasidium pullulans strain DSM14940 and strain DSM14941 (e.g., "Botector" manufactured by bio-ferm, GmbH) and other Aureobasidium spp.; Bacillus amyloliquefaciens strain AT-332 (e.g., "Impression Clear" manufactured by Idemitsu Agri Co., Ltd.) (Registered Trademark)”), Bacillus amyloliquefaciens strain B246 (e.g., "Avogreen (Registered Trademark)" manufactured by "University of Pretoria"), Bacillus amyloliquefaciens strain D747 (e.g.,The following strains of Bacillus amyloliquefaciens are listed: "Bacstar (registered trademark)" manufactured by Etec Crop Solutions, NZ; Bacillus amyloliquefaciens strain DB101 (e.g., "Shelter (registered trademark)" manufactured by Dagutat Bio lab, ZA); Bacillus amyloliquefaciens strain DB102 (e.g., "Artemis (registered trademark)" manufactured by Dagutat Bio lab, ZA); Bacillus amyloliquefaciens strain FZB42 (e.g., "RhizoVital (registered trademark)" manufactured by ABiTEP, DE); Bacillus amyloliquefaciens strain GB03 (e.g., "Kodiak (registered trademark)" manufactured by Bayer Crop Science AG, DE); and Bacillus amyloliquefaciens strain GB03. *Bacillus amyloliquefaciens* strain MBI600 (e.g., Subtilex, manufactured by Becker Underwood, US, a registered trademark), *Bacillus cepacia* (e.g., Deny Stine, manufactured by Microbial Products, a registered trademark), *Bacillus cereus* strain BP01 (e.g., Mepichlor, manufactured by Arysta, US, a registered trademark), *Bacillus firmus* strain I-1582 (e.g., BioNeem, manufactured by AgoGreen, a registered trademark), *Bacillus laterosporus* (e.g., Bio-Tode, manufactured by Agro-Organics, SA, a registered trademark), *Bacillus licheniformis* strain SB3086 (e.g., EcoGuard, manufactured by Novozymes, a registered trademark). Biofungicide (registered trademark)”, Bacillus maroccanus (e.g., manufactured by Micro Flo Company), Bacillus megaterium strain YFM3.25 (e.g., "Bioarc (registered trademark)" manufactured by BioArc), Bacillus metiens (e.g.,Bacillus mycoides isolate J. (e.g., "BmJ" manufactured by "Certis USA" (registered trademark)), Bacillus popilliae (e.g., "Cronox" manufactured by "Bio-Crop, CO" (registered trademark)), Bacillus pumilus strain BU F-33 (e.g., "Integral F-33" manufactured by "Becker Underwood, US" (registered trademark)), Bacillus pumilus strain GB34 (e.g., "Yield Shield" manufactured by "Bayer CropScience AG, DE" (registered trademark)), Bacillus pumilus strain QST2808 (e.g., "Sonata" manufactured by "Bayer CropScience LP, US" (registered trademark)), and Bacillus simplex strain... Simplex strain CGF2856 (e.g., "Momi-Hope Hydrant" manufactured by Arysta Life Science Co., Ltd., a registered trademark), Bacillus sphaericus, particularly antigenic type H5a5b strain 2362 (e.g., "VectoLex" manufactured by Valent BioSciences, US, a registered trademark), Bacillus subtilis (e.g., "Botokiller Hydrant" manufactured by Idemitsu Agri Co., Ltd., a registered trademark), Bacillus subtilis var. amyloliquefaciens strain FZB24 (e.g., "Taegro" manufactured by Novozyme Biologicals, Inc., US, a registered trademark), Bacillus subtilis strain QST713 / AQ713 (e.g., "Bayer CropScienceLP, ... US-made "SERENADE MAX (registered trademark)", Bacillus subtilis strain AQ30002 (e.g., "Serenade-DPZ (registered trademark)"), Bacillus subtilis strain D747 (e.g.,The following products are listed: "Ecoshot (registered trademark)" manufactured by Combinatorial Chemicals Co., Ltd.; Bacillus subtilis strain HAI-0404 (e.g., "Agrocare Hydrate (registered trademark)" manufactured by Nisso Green Co., Ltd.); Bacillus subtilis strain MBI600 (e.g., "Botopika Hydrate (registered trademark)" manufactured by Idemitsu Kosan Co., Ltd.); Bacillus subtilis strain Y1336 (e.g., "Batistar Hydrate (registered trademark)" manufactured by Arysta Life Science Co., Ltd.); Bacillus thuringiensis strain AM65-52 (e.g., "VectoBac (registered trademark)" manufactured by Valent BioSciences, US); and Bacillus thuringiensis israelensis strain BMP144 (e.g., "Becker"). The following are listed as registered trademarks: "Aquabac" (manufactured by Becker Microbial Products, IL); Bacillus thuringiensis subsp. Kurstaki strain BMP 123 (e.g., manufactured by Becker Microbial Products, IL); Bacillus thuringiensis subsp. Kurstaki strain HD-1 (e.g., manufactured by Valent BioSciences, US, "Dipel ES"); Bacillus thuringiensis subsp. aizawai strain ABTS-1857 (SD-1372, e.g., manufactured by Bayer Crop Science AG, DE, "XenTari"); and Bacillus thuringiensis subsp. aizawai antigen type H-7 (e.g., manufactured by Bayer Crop Science AG, DE).The following are listed as trademarks: Florabac WG (registered trademark) manufactured by Valent BioSciences, US; Bacillus thuringiensis subsp. aizawai strain GC-91; Bacillus thuringiensis subspecies Aegypti (e.g., Agerin (registered trademark)); Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428, e.g., Novodor FC (registered trademark) manufactured by BioFa DE); Bacillus thuringiensis var. 7216 (e.g., Amactic and Pethian); and Bacillus thuringiensis var. T36. T36 (e.g., "Cahat"), Bacillus thuringiensis var. Colmeri (e.g., "TianBaoBTc (registered trademark)" manufactured by "Changzhou Jianghai Chemical Factory"), Bacillus thuringiensis var. san diego (e.g., "M-One (registered trademark)" manufactured by "Bacillus thuringiensis var. san diego"), and other Bacillus spp. strains; Beauveria bassiana strain (e.g., "Naturalis (registered trademark)" manufactured by "Intrachem Bio Italia"), Beauveria bassiana strain CG716 (e.g., "BoveMax (registered trademark)" manufactured by "Novozymes"), and Beauveria bassiana strain CG716. Beauveria bassiana strain F-263 (e.g., "Biolisa Madara" manufactured by Idemitsu Kosan Co., Ltd. (registered trademark)), Beauveria bassiana strain GHA (e.g., "Botanigard Hydrate" manufactured by ARYSTA (registered trademark)), Beauveria brongniartii (e.g., ...Beauveria spp. (e.g., "Beaupro" manufactured by Andermatt Biocontrol AG, a registered trademark); Bradyrhizobium japonicum (e.g., "Optimize" manufactured by Novozymes, a registered trademark); Burkholderia spp. strain A396 (e.g., "MBI-206 TGAI" manufactured by Marrone Bio Innovations, a registered trademark); Candida oleophila strain I-82 (e.g., "Aspire" manufactured by Ecogen Inc., US, a registered trademark), Candida oleophila strain O (e.g., "Nexy" manufactured by BioNext, a registered trademark), and Candida saitoana (e.g., manufactured by Biotechnology Research and Development Corporation, a registered trademark). Candida spp. (e.g., "BIOCURE" manufactured by Micro Flo Company, US (BASF SE)); Chaetomium sp. (e.g., "BIOKUPRUM TM" manufactured by AgriLife); Chromobacterium sp. (e.g., "Rivadiom" manufactured by Rivale); Chromobacterium subtsugae strain PRAA4-1T (MBI-203, e.g., "Grandevo" manufactured by Marrone Bio Innovations); Cladosporium cladosporioides (e.g., "Cladosporium"). Cladosporioides (made by) ; Clonostachys rosea f. catenulate strain J1446 (e.g., PRESTOP (registered trademark) made by Verdera, Finland); Colletotrichum gloeosporioides (e.g.,Collego (registered trademark) manufactured by Agriultural Research Initiatives; Coniothyrium minitans strain CON / M / 91-08 (e.g., Contans (registered trademark) manufactured by Encore Technologies, LLC); Cryptococcus albidus (e.g., YieldPlus (registered trademark) manufactured by Anchor Bio-Technologies, ZA); Delftia acidovorans strain RAY209 (e.g., BioBoost (registered trademark) manufactured by Brett Young Seeds); Dilophosphora alopecuri (e.g., Twist Fungus (registered trademark)); Drechslera The following fungi are listed: *Drechslera* sp. (e.g., *Tasumato* herbicide manufactured by Mitsui Chemicals Agro Co., Ltd., a registered trademark); *Entomophthora virulenta* (e.g., *Vektor* manufactured by Ecomic, a registered trademark); *Fusarium oxysporum* sp. (e.g., *Maruka Light* manufactured by Eisai Bioscience Co., Ltd.), *Fusarium oxysporum* sp. (e.g., *Fusaclean* manufactured by Natural Plant Protection, a registered trademark); *Gliocladium catenulatum* sp. (e.g., *Prestop* manufactured by AgBio Inc., a registered trademark); *Gliocladium catenulatum* sp. (e.g., *Prestop* manufactured by AgBio Inc., a registered trademark); *Gliocladium catenulatum* sp. (e.g., *Prestop* manufactured by AgBio Inc., a registered trademark); *Gliocladium catenulatum* sp. (e.g., *Tasumato* herbicide manufactured by Mitsui Chemicals Agro Co., Ltd., a registered trademark); *Gliocladium catenulatum* sp. (e.g., *Prestop* manufactured by AgBio Inc ... Gliocladium sp. (e.g., manufactured by WF Stoneman Company LLC); Hirsutella thompsonii (e.g., Mycohit and ABTEC manufactured by Agro Bio-tech Research Centre, IN); Lactobacillus acidophilus (e.g., ...Fruitsan (registered trademark) manufactured by Inagrosa-Industrias Agrobiologicas, SA; Lactobacillus plantarum strain BY (e.g., Lactoguard hydration solution manufactured by Meiji Seika Pharma Co., Ltd.); Lactobacillus sp. (e.g., Lactoplant (registered trademark) manufactured by LactoPAFI); conidia of Lecanicillium lecanii strain KV01 (e.g., Mycotal (registered trademark) manufactured by Koppert / Arysta); Metarhizium anisopliae strain F52 (e.g., BIO 1020 (registered trademark) manufactured by Bayer CropScience); Metarhizium anisopliae strain F52. The following fungi are listed: *Metarhizium anisopliae* strain SMZ-2000 (e.g., PIRATES granules manufactured by Arysta Life Science, Inc., a registered trademark); *Metarhizium anisopliae var. acridum* (e.g., Green Muscle manufactured by Biological Control Products, a registered trademark); *Metarhizium anisopliae var. acridum* (e.g., GreenGuard manufactured by Becker Underwood, US, a registered trademark); *Metschnikowia fructicola* (e.g., Shemer manufactured by Bayer CropScience, a registered trademark); *Microdochium dimerum* (e.g., ANTIBOT manufactured by Agrauxine, France, a registered trademark); *Microsphaeropsis* ochracea) (for example,Microx (registered trademark) manufactured by Prophyta; Monacrosporium phymatopagum (Nemahiton (registered trademark) manufactured by Tomoe Chemical Industry Co., Ltd.); Mucor haemelis (e.g., BioAvard (registered trademark) manufactured by Indore Biotech Inputs & Research); Myrothecium verrucaria strain AARC-0255 (e.g., DiTera™ (registered trademark) manufactured by Valent Biosciences); Ophiostoma piliferum strain D97 (e.g., Sylvanex); Paecilomyces fumosoroseus strain apopka 97 (e.g., PreFeRal (registered trademark) WG manufactured by Biobest); Paecilomyces fumosoroseus strain apopka 97 Paecilomyces fumosoroseus strain FE 9901 (e.g., "No Fly (registered trademark)" manufactured by Natural Industries Inc. (Novozymes company)), Paecilomyces fumosoroseus (e.g., "Preferred Hydrant" manufactured by Tokai Corporation), 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., "Gottsu A (registered trademark)" manufactured by Idemitsu Kosan Co., Ltd.), Paecilomyces variegata *Paecilomyces* spp., such as *Paecilomyces variotii* strain Q-09 (e.g., *Nemaquim* manufactured by "Quimia, MX" (registered trademark)); *Paecilomyces polymyxa* strain AC-1 (e.g., *Topseed* manufactured by "Green Biotech Company Ltd." (registered trademark)); *Paecilomyces poppiliae* strain (e.g., ...The following are examples of *Paenibacillus* spp.: *Milky spore disease* (manufactured by St. Gabriel Laboratories, a registered trademark); *Pasteuria nishizawa* (e.g., *Clariva* (registered trademark)), *Pasteuria nishizawae* (e.g., *oyacystLF / ST* (manufactured by Pasteuria Bioscience, a registered trademark)), *Pasteuria penetrans* (e.g., *Pasteuria* (registered trademark) manufactured by Pasteuria Bioscience), and other *Pasteuria* spp.; *Pectobacterium carotovorum* (e.g., *Biokeeper* (registered trademark) manufactured by Nissan Chemical Co., Ltd.), and *Pectobacterium carotovorum*. Pectobacterium spp. strains such as *Carotovorum* CGE234M403 (e.g., "Ecomate" (registered trademark) manufactured by "Combinatorial Chemistry"), Penicillium bilaii strain (e.g., "Jump Start" (registered trademark) manufactured by "Novozymes"), Phlebiopsis gigantea strain FOC PG B22 / SP1190 / 3.2 (e.g., "ROTSOP" (registered trademark) manufactured by "Verdera, Finland"), Phoma macrostroma strain 94-44B (e.g., "Phoma H" (registered trademark) manufactured by "Scotts, US"), and Pochonia chlamydosporia var. catenulata (e.g., "The National Center of Animal and Plant Health Care") Health (CENSA); "KlamiC (registered trademark)" manufactured by "CU"); Pseudomonas aureofaciens strain TX-1 (e.g., "Spot-Less Biofungicide (registered trademark)" manufactured by "Eco Soils Systems, CA"); Pseudomonas chlororaphis strain 63-28 (e.g.,The following strains of Pseudomonas chlororaphis are listed: ATEze (registered trademark) manufactured by EcoSoil Systems; Pseudomonas chlororaphis strain MA 342 (e.g., Cedomon (registered trademark) manufactured by Bioagri,S); Pseudomonas fluorescens strain 1629RS (e.g., Frostban D (registered trademark) manufactured by Frost Technology Corp); Pseudomonas fluorescens strain A506 (e.g., Blightban (registered trademark) manufactured by Blightban); Pseudomonas fluorescens strain FPT-9601 (e.g., Konae Fukudo (registered trademark) manufactured by Toki Chemical Co., Ltd.); and Pseudomonas fluorescens strain A506 (registered trademark). Mixtures of *Pseudomonas fluorescens* strain FPT-9601 and strain FPH-9601 (e.g., *Cell Nae Genki* manufactured by Toki Chemical Co., Ltd., a registered trademark), *Pseudomonas fluorescens* strain G7090 (e.g., *Vegekeeper* manufactured by Arysta Life Science Co., Ltd., a registered trademark), *Pseudomonas proradix* (e.g., *Proradix* manufactured by Sourcon Padena, a registered trademark), *Pseudomonas resinovorans* (e.g., *Solanacure* manufactured by Agricultural Research Council, SA, a registered trademark), *Pseudomonas syringae* strain MA-4 (e.g., *Biosave* manufactured by EcoScience, US, a registered trademark), and *Pseudomonas... Pseudomonas syringae strain 742RS (e.g., "Frost Technology Corp (registered trademark)" manufactured by "Frostban C"), Pseudomonas rhodesiae strain HAI-0804 (e.g., "Masterpiece Hydrate (registered trademark)" manufactured by "Nippon Soda Co., Ltd."), Pseudomonas sp. strain CAB-02 (e.g.,Pseudomonas spp. (e.g., "Momi-Genki Hydrate" manufactured by Nissan Chemical Industries, Ltd.); Pseudozyma sp. (e.g., "Pseudozyma aphidis" manufactured by Yissum Research Development Company of the Hebrew University of Jerusalem), Pseudozyma flocculosa strain PF-A22 UL (e.g., "Sporodex L" (registered trademark) manufactured by Plant Products Co. Ltd, CA); Pythium oligandrum strain DV74 or M1 (e.g., "Polyversum" (registered trademark) manufactured by Bioprepraty, CZ); Reynoutria sachlinensis (e.g., "REGALIA" (registered trademark) manufactured by Marrone BioInnovations, US); Rhizopogon Rhizopogon spp. (e.g., Myco-Sol manufactured by Helena Chemical Company, a registered trademark), Rhizopogon fulvigleba (e.g., Myco-Sol manufactured by Helena Chemical Company, a registered trademark), etc.; Saccharomyces cerevisiae strains (e.g., manufactured by Lesaffre et Compagnie, FR); Sclerotinia minor (e.g., Sarritor manufactured by Agrium Advanced Technologies, a registered trademark); Serratia entomophila (e.g., Invade manufactured by Wrightson Seeds, a registered trademark); Sporothrix insectorum (e.g., Sporothrix manufactured by Biocerto; BR, a registered trademark). Es (registered trademark)); Stagonospora phaseoli (e.g., commercially available from "Syngenta"); Streptomyces acidiscabies strain RL-110T (e.g.,Streptomyces spp., including *MBI-005EP* (registered trademark) manufactured by Marrone Bioinnovations, CA; *Streptomyces candidus* strain Y21007-2 (e.g., *BioBac* (registered trademark) manufactured by Biontech, TW); *Streptomyces galbus* strain K61 (e.g., *Mycostop* (registered trademark) manufactured by Verdera); *Streptomyces lydicus* strain WYEC108 (e.g., *ACTINOVATE* (registered trademark) manufactured by Natural Industries, US); and *Streptomyces saraceticus* (e.g., *Clanda* (registered trademark) manufactured by A & A Group (Agro Chemical Corp.)). Talaromyces flavus strain B-422 (e.g., "Momi-keeper (registered trademark)" manufactured by Central Glass Ltd.), Talaromyces flavus strain SAY-Y-94-01 (e.g., "Tough Block (registered trademark)" manufactured by Idemitsu Kosan Ltd.), Talaromyces flavus strain V117b (e.g., "PROTUS (registered trademark) WG" manufactured by Prophyta, DE), and other Talaromyces spp.; Thiobacillus sp. (e.g., "Cropaid (registered trademark)" manufactured by Cropaid Ltd, UK); Trichoderma album (e.g., known as a product of "Bio-Zeid"), Trichoderma asperellum strain ICC 012 (e.g., manufactured by "Isagro"), Trichoderma... Trichoderma asperellum strain T34 (e.g., "T34 Biocontrol (registered trademark)" manufactured by "Bioncontrol Technologies, ES"), Trichoderma asperellum strain SKT-1 (e.g., "ECO-HOPE (registered trademark)" manufactured by "Combined Chemical Industries Co., Ltd."), Trichoderma atroviride strain (e.g., ..."Esquive (registered trademark) WP" manufactured by "Agrauxine, FR", Trichoderma atroviride strain LC52 (e.g., "Tenet (registered trademark)" manufactured by "Agrimm Technologies Ltd, NZ"), Trichoderma atroviride strain SKT-1 (e.g., "Ecohope DJ (registered trademark)" manufactured by "Combined Chemical Industries Co., Ltd."), Trichoderma gamsii strain ICC 080 (e.g., "BIO-TAMTM (registered trademark)" manufactured by "Bayer Crop Science LP, US"), Trichoderma harzianum strain DB 103 (e.g., "T-Gro 7456 (registered trademark)" manufactured by "Dagutat Biolab ... Trichoderma harzianum strain ITEM908 (e.g., "Trianum-P" manufactured by "Koppert" (registered trademark)), Trichoderma harzianum strain KD (e.g., "Trichoplus" manufactured by "Biological Control Products, SA" (registered trademark)), Trichoderma harzianum strain TH-35 (e.g., "ROOT PRO" manufactured by "Mycontrol Ltd." (registered trademark)), Trichoderma harzianum rifai strain T-22 (KRL-AG2, e.g., "PLANTSHIELD T-22G" manufactured by "Firma BioWorks Inc. US" (registered trademark)), Trichoderma harzianum rifai strain T-39 (e.g., "TRICHODEX" manufactured by "Makhteshim Ltd, US" (registered trademark)), Trichoderma lignin Trichoderma lignorum strain TL-0601 (e.g., "Mycotric" manufactured by Futureco Bioscience, ES (registered trademark)), Trichoderma polysporum strain (e.g., "Binab TF WP" manufactured by BINAB Bio-Innovation AB, Sweden (registered trademark)), Trichoderma stromaticum strain (e.g.,Trichoderma spp., including "TRICOVAB (registered trademark)" manufactured by "Ceplac; Brazil", Trichoderma virens (also known as "Gliocladium virens") strain GL-21 (e.g., "SOILGARD (registered trademark)" manufactured by "Certis LLC, US"), Trichoderma viride strain ICC080 (e.g., "REMEDIER (registered trademark) WP" manufactured by "Isagro Ricerca, ITALIA"), and Trichoderma viride strain TV1 (e.g., "Trianum-P (registered trademark)" manufactured by "Koppert"); Tsukamurella paurometabola strain C-924 (e.g., "HeberNem (registered trademark)"); and Ulocladium. HRU3 of *Verticillium oudemansii* (e.g., "Botry-Zen (registered trademark)" manufactured by "Botry-Zen Ltd, NZ"); CGF4526 of *Variovorax paradoxus* (e.g., "FieldKeeper Hydrate (registered trademark)" manufactured by "Central Glass"); *Vesicular-Arbuscular Mycorrhiza* mycorrhizae (e.g., "Dr Kinkon (registered trademark)" manufactured by "Idemitsu Agri"); WCS850 of *Verticillium alboatrum* (e.g., "Dutch Trig (registered trademark)" manufactured by "Tree Care Innovations"), IMI 179172 of *Verticillium lecanii* (e.g., "Vertalec (registered trademark)" manufactured by "Arysta Life Science Co., Ltd."), and IMI of *Verticillium lecanii*. 263817 (e.g., "Mycotal" manufactured by Arysta Life Science Co., Ltd. (registered trademark)) and other Verticillium spp.; Xanthomonas campestris (e.g., Camperico liquid available from Tomo Chemicals (registered trademark)), etc.

[0192] Furthermore, in recent years, IPM (Integrated Disease Management) technology, which utilizes insect sex pheromones (e.g., mating disruptors for leafrollers and armyworms), natural enemy insects, etc., has been advancing. The agent of the present invention can be used in conjunction with such technology or systematically. For example, it can also be used together with thrips, striped thrips, leafminer parasitic wasps, encarsia formosa, blunt-eyed ticks, cucumber wasps, cucumber neoseiform mites, mulberry wasps, Coleman wasps, pungent wasps, potato gall midges, Swáski phytosei, southern black-flowered stink bugs, Montgomery's horn wasps, Chilean phytoseiform mites, alfalfa striped aphid wasps, aphid wasps, degenerate phytoseiform mites, Trichogramma wasps (wases), heterochromia ladybugs, East Asian small-flowered stink bugs, leaf miners, green leaf miners, tortoise-shell ladybugs, dwarf tortoise-shell ladybugs, Miyako phytoseiform mites, Ryukyu glossy ladybugs, *Rhizoctonia* spp., *F. candida*, and *A. flavescens*, etc. ("Collection of Collection and Infectious Plant Pathogens (*Rhizoctonia*", Chemistry and Biology, Vol. 51, No. 4, 2013) (as recorded on pages 267-269) Natural enemies of species such as the ruby ​​parasitic wasp, Japanese lacewing, European giant wasp, and lemon phytosei mite.

[0193] *Abbreviata 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.; *Filipjevimermis* leipsandra); Gastromermis spp.; Gongylonema spp.; Gynopoecilia pseudovipara; Heterorhabditis bacteriophora (e.g., known as a product of "B-Green"), Heterorhabditis baujardi, Heterorhabditis heliothidis (e.g., known as a product of "Nematon"), Heterorhabditis indica, Heterorhabditis marelatus, Heterorhabditis megidis, Heterorhabditis zealandica, and other Heterorhabditis species. spp.); 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 culicis*; *Phasmarhabditis hermaphrodita*; *Physaloptera* spp.; *Protrellatus* spp.; *Pterygodermatites* spp.; *Romanomermis* spp.; *Seuratum* cadarachense); Sphaerulariopsis spp.; Spirura guianensis; Steinernema carpocapsae (e.g., known as a product of "Biocontrol", or "BIOSAFE (registered trademark)" manufactured by "SDS Bio Tech Co., Ltd."); Steinernema feltiae (e.g., known as a product of "Nemasys (registered trademark)"); Steinernema glaseri (e.g., known as a product of "Arysta Life Science Co., Ltd." or "Biotopia (registered trademark)"); Steinernema kraussei (e.g., known as a product of "Larvesure"); Steinernema kraussei (the prototype of entomopathic diseases). kushidai (e.g., "Shibashi Nema" manufactured by "KUBOTA Co., Ltd."), Steinernema riobrave (e.g., known as a product of "Biovector"), Steinernema scapterisci (e.g., known as a product of "Nematac S"), Steinernema scarabaei, Steinernema siamkayai, and other species of Steinernema spp.); Strelkovimermis peterseni; Subulura spp.; Sulphuretylenchus elongatus; Tetrameres spp.; natural enemy nematodes.

[0194] Tobacco stripe virus, apple leafroller (Adoxophyes orana) granular virus (GV) (e.g., known as a product of "BIOFA-Capex (registered trademark)"), a mixture of apple leafroller (Adoxophyes orana) granular disease virus (MAFF632001) and tea leafroller granular disease virus (MAFF632002) (e.g., "Hamaki Enemy (registered trademark)" manufactured by "Arysta Life Science Co., Ltd."), tulip moth (Agrotis segetum) nucleopolyhedrovirus (NPV), bean leafroller (Anticarsia gemmatalis) (Woolly pyrol moth) mNPV (e.g., known as a product of "Polygen (registered trademark)"), California alfalfa looper (Autographacalifornica) (Alfalfa Looper) mNPV (e.g., known as a product of "VPN80 (registered trademark)"); Supplier: Agricola El Sol), Tea Looper (Biston suppressaria) NPV, Silkworm (Bombyx mori) NPV, False Codling Moth (Cryptophlebia leucotreta) GV (e.g., known as products of "Cryptex (registered trademark)"), Codling Moth Granulation Virus (Cydia pomonella spp.), viruses, Codling Moth Granulation Virus (CpGV) (e.g., known as products of "Madex Plus (registered trademark)"), Dendrolimus punctatus CPV (e.g., DVC hydration agent "Matsukemin" manufactured by Chugai Pharmaceutical), Helicoverpa Armigera NPV (e.g., known as products of "AgBiTech-ViVUS Max (registered trademark)"), Cotton Bollworm (Helicoverpa armigera) zea (formerly Heliothis zea) NPV (e.g., known as products of "Elcar (registered trademark)"), Leucoma salicis NPV, Lymantria dispar NPV (e.g., known as products of "Gypcheck (registered trademark)"), Neodiprion abietis NPV (e.g.,Known as products under the "Abietiv (registered trademark)" brand, the following are listed: Neodiprion lecontei (red-headed pine sawfly) NPV (e.g., known as products under the "Lecontvirus (registered trademark)" brand), Neodiprion sertifer NPV (e.g., known as products under the "Neocheck-S (registered trademark)" brand), Orgyia pseudotsugata (pine tussock moth) NPV (e.g., known as products under the "Virtuss (registered trademark)" brand), Phthorimaea operculella (potato tuber moth) GV (e.g., known as products under the "Matapol (registered trademark)" brand), Pieris rapae (white white butterfly) GV, Plutella xylostella (diamond moth) GV (e.g., known as products under the "Plutec (registered trademark)" brand), and Spodoptera (fallen leaf moth). albula (Grey Striped Leaf Moth) mNPV (e.g., known as a product of "VPN 82 (registered trademark)"), Spodoptera exempta (Fall Armyworm) mNPV (e.g., known as a product of "Spodec (registered trademark)"), Spodoptera exigua (Beet armyworm) mNPV (e.g., known as a product of "Spexit (registered trademark)"; supplier: Andermatt Biocontrol), Spodoptera frugiperda (Fall Armyworm) mNPV (e.g., known as a product of "Baculovirus VPN (registered trademark)"), Spodoptera littoralis (Between Noctuid Moth) NPV (known as a product of "Spodoptrin (registered trademark)"; supplier: NPP Calliope France), Spodoptera (Between Noctuid Moth) Littovir (registered trademark) NPV, beet armyworm nucleopolyhedrovirus Fu-1 strain embedding (HASMON Enemy manufactured by Nippon Kayaku Co., Ltd.), beet armyworm nucleopolyhedrovirus strains A9 and C3 embedding (e.g., HASMON KILLER manufactured by Ibikawa Kogyo Co., Ltd.), zucchini yellow spot virus attenuated strain ZY-02 (e.g., "Kyoto Micro-Research Q Bio ZY-02 (registered trademark)" manufactured by the Microbial Chemistry Research Institute Co., Ltd.), zucchini yellow spot virus attenuated strain ZY-95 (e.g.,Virus agents such as "Kyoto Micro-Research Q Bio ZY (registered trademark)" manufactured by "Microbial Chemistry Research Institute Co., Ltd.", and the attenuated strain of tomato mosaic virus AVP08 (e.g., "Green Paper PM (registered trademark)" manufactured by "Microbial Chemistry Research Institute Co., Ltd."), etc.

[0195] Vegetable, tuber, legume, flower and foliage plant attractants (Confuser V (registered trademark) manufactured by "Hsieh-Yu Agri Co., Ltd."), Cuelure liquid (e.g., "Cuelure (registered trademark) manufactured by "Sankei Chemical Co., Ltd."), methyl eugenol agent (e.g., "Sankei Methyl Eugenol (registered trademark) manufactured by "Sankei Chemical Co., Ltd."), Synanthelure agent (fruit tree pest control agent) (Sukashiba-con-L (registered trademark) manufactured by "Shin-Etsu Chemical Co., Ltd."), mating attractant (Bokutokon-H (registered trademark) manufactured by "Shin-Etsu Chemical Co., Ltd."), cutworm attractant (Hamakicon-N (registered trademark) manufactured by "Shin-Etsu Chemical Co., Ltd."), mating inhibitor for fruit tree pests (Confuser V (registered trademark) manufactured by "Hsieh-Yu Agri Co., Ltd."). Peach and plum tree pest control agent (Confuser N (registered trademark) manufactured by Shin-Etsu Chemical Co., Ltd.), peach pest control agent (Confuser MM (registered trademark) manufactured by Shin-Etsu Chemical Co., Ltd.), apple pest control agent (Confuser AA (registered trademark) manufactured by Shin-Etsu Chemical Co., Ltd.), persimmon fruit moth control agent (Hetamushicon (registered trademark) manufactured by Shin-Etsu Chemical Co., Ltd.), net attractant (NITOLURE <Ameshiro> (registered trademark) manufactured by Idemitsu Kosan Co., Ltd.), oak bark beetle attractant (Kashinagacol (registered trademark) manufactured by Sankei Chemical Co., Ltd.), lawn pest control agent (e.g., Confuser G (registered trademark) manufactured by Shin-Etsu Chemical Co., Ltd.), MEP sweet potato pest control granules (Sankei... The following pesticides are listed: "Arimodoxikor granules (registered trademark)" manufactured by Sankei Chemical Co., Ltd.; "Yotoukon-1 (registered trademark)" manufactured by Shin-Etsu Chemical Co., Ltd.; Ochimeranoura (sugarcane pest control agent) (e.g., "Sankei Okimelanocall (registered trademark)" manufactured by Sankei Chemical Co., Ltd.); Sakimelanocol (registered trademark) manufactured by Sankei Chemical Co., Ltd.; and worm disruptor (e.g., [unclear text - likely related to click beetle control agents]).Hormonal agents such as "Yotokon-S (registered trademark)" manufactured by Shin-Etsu Chemical Co., Ltd., beet armyworm control agents (e.g., "Ferrodin SL (registered trademark)" manufactured by Sumitomo Chemical Co., Ltd.), diamondback moth, beet armyworm, and polar tiger control agents (e.g., "Konagacon (registered trademark)" manufactured by Sankei Chemical Co., Ltd.), etc.

[0196] Acacia negra extract, abscisic acid, Chenopodium ambrosiodae extract, arginine, arginine oligosaccharide, Nepitella oil, eugenol, L-carvone, ethyl formate, chitin, chitosan (e.g., "ARMOUR-ZEN" manufactured by BotriZen Ltd., NZ), quiillay extract, and ginkgolides A, B, C, J, and M. The selected components in group M include ginkgo biloba extract, grapefruit seed and pulp extract, potassium silicate, cytokinin, sanguinarine (derived from bamboo-like grass), cis-jasmone, citral, gibberellin derivative, siccanin (a substance produced by the filamentous fungus Helminthosporium siccans), citronella oil, citronellol, jasmonic acid, methyl jasmonate, sorbitol actanoate, neem (neem tree; extract from neem tree seeds), and neem oil. Oil), thymol, terpinolene, and terpenes from the extract of synthetically produced Chenopodium ambrosioides near ambrosioides [as a bioactive ingredient, it contains a mixture of three types of terpenes, namely α-terpinene, p-cymene, and limonene] (for example, products known as "Requiem (registered trademark)").Suppliers: Bayer Crop Science LP, US; Bilobalide; Humic Acid and fulvic acid extracted from lignite clay; Pentatermanone; Marigold Oil; Isopropyl Myristate; Methyl Eugenol; Methyl Jasmonate; Harpin Protein; Heptyl Butyrate; Lavandulyl Senecioate; Lignite, known as a potassium humate powder (leonardite). Humic acids such as coal, lecithin, (E,Z)-7,9-dodecadien-1-yl acetate, (E,Z)-2,4-ethyldecadienoate (pear ester), (Z,Z,E)-7,11,13-hexadecanetrialdehyde, 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-octane-3-ol, (E,Z,Z)-3,8,11-tetradecanetrien acetate, (Z,E)-9,12-tetradecadien-1-yl acetate, Z-7-tetradecene Z-2-one, Z-9-tetradecen-1-ylacetate, Z-11-tetradecenal, Z-11-tetradecen-1-ol, plumbagin (an extract from plants of the genera *Pongamia*, *Calotropis*, *Plumbago*, *Maytenus*, *Baccharis*, *Rubia*, *Calophyllum*, *Urtica*, *Kobresia*, and *Caesalpinia*), and Rhodopseudomonas. speroides, particularly, extracts of organisms such as brassinosteroids produced by strain IFO-12203; and harpin (a protein isolated from Erwinia amylovora).For example, products known as "Harp-N-Tek (registered trademark)," "Messenger (registered trademark)," "Employ (registered trademark)," and "ProAct (registered trademark)" are examples. [Example];

[0197] The following are representative embodiments of the present invention, but the present invention is not limited to these.

[0198] Preparation Example 1: Preparation of 2-(4-(tri-butyl)phenyl)-N-((5-methylpyridin-2-yl)methyl)-3,3-dimethyloxocyclopropane-2-carboxylic acid (compound number A-14), (compound number A-14a) and (compound number A-14b) Preparation of 2-(4-(tri-butyl)phenyl)-3,3-dimethyloxocyclopropane-2-carboxylic acid (compound number E-1): A solution of 2-(4-(tri-butyl)phenyl)-3-methylbut-2-enoic acid (0.12 g, 0.50 mmol) in chloroform (2.0 mL) was added, and m-chloroperbenzoic acid (65 wt%, 0.15 g, 0.55 mmol) was added and stirred overnight at room temperature. After the reaction was complete, an aqueous solution of sodium thiosulfate and ethyl acetate were added to the reaction solution for extraction. The organic layer was dried with anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 2-(4-(tributyl)phenyl)-3,3-dimethyloxocyclopropane-2-carboxylic acid as the crude product. It was used in the next step without further purification.

[0199] Preparation Examples 1-2 2-(4-(tri-butyl)phenyl)-N-((5-methylpyridin-2-yl)methyl)-3,3-dimethyloxocyclopropane-2-carboxylamine (Compound No. A-14), (Compound No. A-14a) and (Compound No. A-14b) were prepared from a THF (7.1 mL) solution of 0.50 mmol of 2-(4-(tri-butyl)phenyl)-3,3-dimethyloxocyclopropane-2-carboxylic acid obtained in Preparation Example 1-1, with the addition of (5-methylpyridin-2-yl)methylamine hydrochloride (0.20 g, 1.3 mmol), triethylamine (0.79 mL, 5.7 mmol), 2-chloro-1-methylpyridinium iodide (0.51 g, 2.0 mmol) and 4-dimethylaminopyridine (13 mg, 0.11 mmol), heated under reflux for 4 hours. After the reaction was complete, saturated ammonium chloride aqueous solution was added to the reaction solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was purified by silicone column chromatography to obtain 2-(4-(tributyl)phenyl)-N-((5-methylpyridin-2-yl)methyl)-3,3-dimethyloxocyclopropane-2-carboxyamine (50 mg, 0.14 mmol). Yield: 28% (2 steps) Properties: Melting point: 84-86℃

[0200] The racemic mixture of 2-(4-(tri-butyl)phenyl)-N-((5-methylpyridin-2-yl)methyl)-3,3-dimethyloxocyclopropane-2-carboxylamine obtained in Examples 1-2 was subjected to optical analysis using a chiral column (CHIRALPAK ID (Daicel), 4.6 mm × 150 mm, 5 μm, detector: 220 nm) at a column temperature of 35 °C and a mobile phase flow rate of 1 mL / min (0.05% trifluoroacetic acid in H2O / MeCN = 600 / 400 (v / v)). The results were obtained as compound A-14a (holding time 3.3 min) and compound A-14b (holding time 4.6 min). Compound A-14a melting point: 121-123℃ Compound A-14b melting point: 121-123℃

[0201] Manufacturing Example 2 Manufacturing of 6-((2-(4-(tri-butyl)phenyl)-3,3-dimethyloxocyclopropane-2-carboxylamine)methyl)-2,3-dimethylpyridine 1-oxide (compound number A-3) Manufacturing Example 2-1 Manufacturing of 2-(4-(tri-butyl)phenyl)-N-((5,6-dimethylpyridin-2-yl)methyl)-3-methylbut-2-enylamine In a THF (1.0 mL) solution of 2-(4-(tri-butyl)phenyl)-3-methylbut-2-enoic acid (58 mg, 0.25 mmol), (5,6-dimethylpyridin-2-yl)methylamine dihydrochloride (63 mg, 0.30 mmol), triethylamine (0.13 g, 1.3 mmol), and 2-chloro-1-methylpyridinium iodide (0.13 g, The reaction mixture was heated under reflux for 3 hours with 0.50 mmol of 4-dimethylaminopyridine (3.0 mg, 0.025 mmol). After the reaction was complete, saturated ammonium chloride aqueous solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was purified by silicone column chromatography to obtain 2-(4-(tributyl)phenyl)-N-((5,6-dimethylpyridin-2-yl)methyl)-3-methylbut-2-enylamine (60 mg, 0.17 mmol). Yield: 68% Properties: 1H-NMR (CDCl3): δ 7.37 (d, 2H), 7.33 (d, 1H), 7.17 (d, 2H), 6.96 (d, 1H), 6.57 (s, 1H), 4.47 (d, 2H), 2.37 (s, 3H), 2.22 (s, 3H), 2.15 (s, 3H), 1.69 (s, 3H), 1.33 (s, 9H)

[0202] Preparation Example 2-2: 6-((2-(4-(tri-butyl)phenyl)-3,3-dimethyloxocyclopropane-2-carboxylamine)methyl)-2,3-dimethylpyridine 1-oxide (compound number A-3) was prepared by adding a chloroform (1.0 mL) solution of 2-(4-(tri-butyl)phenyl)-N-((5,6-dimethylpyridin-2-yl)methyl)-3-methylbut-2-enylamine (60 mg, 0.17 mmol) to m-chloroperbenzoic acid (65 wt%, 91 mg, 0.34 mmol) and stirring overnight at room temperature. After the reaction was complete, an aqueous solution of sodium thiosulfate and ethyl acetate were added to the reaction solution for extraction. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 6-((2-(4-(tert-butyl)phenyl)-3,3-dimethyloxocyclopropane-2-carboxylamine)methyl)-2,3-dimethylpyridine 1-oxide (65 mg, 0.17 mmol). Yield: 99% Properties: 1H-NMR (CDCl3): δ 7.75 (t, 1H), 7.51 (d, 2H), 7.33 (d, 2H), 7.12 (d, 1H), 7.00 (d, 1H), 4.58 (dd, 2H), 2.51 (s, 3H), 2.32 (s, 3H), 1.32 (s, 3H), 1.29 (s, 9H), 1.02 (s, 3H)

[0203] Manufacturing Example 3 Manufacturing of 2-(4-(tri-butyl)phenyl)-N-((5,6-dimethylpyridin-2-yl)methyl)oxocyclopropane-2-carboxylic acid (Compound No. A-2) Manufacturing Example 3-1 Manufacturing of 2-(4-(tri-butyl)phenyl)-N-((5,6-dimethylpyridin-2-yl)methyl)-2-sideoxyacetamide In a THF (4.0 mL) solution of 2-(4-(tri-butyl)phenyl)-2-sideoxyacetic acid (0.21 g, 1.0 mmol), (5,6-dimethylpyridin-2-yl)methylamine dihydrochloride (0.25 g, 1.2 mmol), triethylamine (0.51 g, 5.0 mmol), and 2-chloro-1-methylpyridinium iodide (0.51 g, 1.0 mmol) were added. 2.0 mmol) and 4-dimethylaminopyridine (12 mg, 0.10 mmol) were added and the mixture was heated under reflux for 3 hours. After the reaction was completed, saturated ammonium chloride aqueous solution was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silicone column chromatography to obtain 2-(4-(tributyl)phenyl)-N-((5,6-dimethylpyridin-2-yl)methyl)-2-sideoxyacetamide (0.21 g, 0.65 mmol). Yield: 64% Properties: 1H-NMR (CDCl3): δ 8.29 (d, 2H), 8.09 (s, 1H), 7.50 (d, 2H), 7.39 (d, 1H), 7.04 (d, 1H), 4.61 (d, 2H), 2.51 (s, 3H), 2.27 (s, 3H), 1.35 (s, 9H)

[0204] Preparation Example 3-2 2-(4-(tri-butyl)phenyl)-N-((5,6-dimethylpyridin-2-yl)methyl)oxocyclopropane-2-carboxylamine (Compound No. A-2) was prepared by adding a solution of trimethylolpropane iodide (0.11 g, 0.48 mmol) in dimethyl sulfoxide (1.0 mL), and then adding potassium tributoxy (49 mg, 0.48 mmol). The mixture was stirred at room temperature for 1 hour under argon atmosphere. A solution of 2-(4-(tri-butyl)phenyl)-N-((5,6-dimethylpyridin-2-yl)methyl)-2-oxoacetamide (0.14 g, 0.44 mmol) in dimethyl sulfoxide (1.0 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hours. After the reaction was complete, water and ethyl acetate were added to the reaction mixture for extraction. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 2-(4-(tributyl)phenyl)-N-((5,6-dimethylpyridin-2-yl)methyl)oxocyclopropane-2-carboxylamine (53 mg, 0.16 mmol). Yield: 36%. Properties: 1H-NMR (CDCl3): δ 7.57 (d, 2H), 7.40 (d, 2H), 7.35 (d, 1H), 6.97 (d, 1H), 4.48 (d, 2H), 3.27 (d, 1H), 3.10 (d, 1H), 2.46 (s, 3H), 2.52 (s, 3H), 1.31 (s, 9H).

[0205] Preparation Example 4 Preparation of 2-(4-(2,2-dimethylpropyl)phenyl)-N-((pyridin-2-yl)methyl)-3,3-dimethyloxocyclopropane-2-carboxamide (Compound No. A-86) Preparation Example 4-1 Preparation of 2-(4-(2,2-dimethylpropyl)phenyl)oxocyclopropane-3,3-dimethyl-2-carboxamide Potassium carbonate (90 mg, 0.66 mmol) was added to a solution of 2-(4-(2,2-dimethylpropyl)phenyl)oxocyclopropane-3,3-dimethyl-2-carboxynitrile (0.80 g, 3.3 mmol) in 13 mL of dimethyl sulfoxide, and 30% hydrogen peroxide (0.37 mL, 3.6 mmol) was added dropwise. The mixture was stirred at room temperature for 4 hours. The reaction was stopped by adding an aqueous solution of sodium thiosulfate to the reaction solution, extracted with ethyl acetate, and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 2-(4-(2,2-dimethylpropyl)phenyl)oxocyclopropane-3,3-dimethyl-2-carboxymethylamine (0.82 g, 3.1 mmol). Yield: 95%. Properties: 1H-NMR (CDCl3): δ 7.49 (d, 2H), 7.11 (d, 2H), 6.36 (br s, 1H), 5.35 (br s, 1H), 2.48 (s, 2H), 1.52 (s, 3H), 1.06 (s, 3H), 0.89 (s, 9H).

[0206] Preparation Example 4-2 Preparation of 2-(4-(2,2-dimethylpropyl)phenyl)-N-((pyridin-2-yl)methyl)-3,3-dimethyloxocyclopropane-2-carboxamide (Compound No. A-86) 2-(4-(2,2-dimethylpropyl)phenyl)oxocyclopropane-3,3-dimethyl-2-carboxamide (0.10 g, 0.38 mmol), 2-(chloromethyl)pyridine hydrochloride (69 mg, 0.42 mmol), and cesium carbonate (0.31 g, 0.96 mmol) were dissolved in N,N-dimethylacetamide (2.0 mL) and stirred at 80 °C for 4 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2-(4-(2,2-dimethylpropyl)phenyl)-N-((pyridin-2-yl)methyl)-3,3-dimethyloxocyclopropane-2-carboxylamine (48 mg, 0.14 mmol). Yield: 36% Physical properties: 1H-NMR (CDCl3): δ 8.56-8.54 (m, 1H), 7.62 (dt, 1H), 7.55-7.48 (m, 3H), 7.22-7.16 (m, 2H), 7.10 (d, 2H), 4.65-4.43 (m, 2H), 2.48 (s, 2H), 1.44 (s, 3H), 1.06 (s, 3H), 0.89 (s, 9H)

[0207] Manufacturing of Intermediates Example 1 Manufacturing of Intermediates of 2-(4-(tri-butyl)phenyl)-3,3-dimethyloxocyclopropane-2-carboxylic acid (Compound No. E-1a) Example 1-1 Manufacturing of Intermediates of (2-(4-(tri-butyl)phenyl)-3,3-dimethyloxocyclopropane-2-yl)methanol In a solution of titanium(IV) isopropoxide 1.3 g, 4.4 mmol) in dichloromethane (23 mL), D-(-)-diethyl tartrate (1.2 g, 5.6 mmol) and cumene hydroperoxide (1.1 g, 7.4 mmol) were added at room temperature. After stirring for 5 minutes, the reaction solution was cooled to -5 °C, and a solution of 2-(4-(tri-butyl)phenyl)-3-methyl-2-buten-1-ol (0.84 g, 3.7 mmol) in dichloromethane (3.0 mL) was added dropwise. After the addition was complete, the mixture was heated to room temperature and stirred for 3 hours. After the reaction was complete, 9.6 mL of 3M NaOH aqueous solution was added to the reaction solution, and the mixture was stirred at room temperature for 30 minutes. Then, saturated sodium thiosulfate aqueous solution was added to stop the reaction. The reaction solution was filtered through diatomaceous earth, extracted with ethyl acetate, and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain (2-(4-(tributyl)phenyl)-3,3-dimethyloxocyclopropane-2-yl)methanol (0.36 g, 1.5 mmol). Yield: 41% Properties: 1H-NMR (CDCl3): δ 7.37 (d, 2H), 7.27 (d, 2H), 4.01 (m, 2H), 1.53 (s, 3H), 1.32 (s, 9H), 1.02 (s, 3H) The obtained (2-(4-(tributyl)phenyl)-3,3-dimethyloxocyclopropane-2-yl)methanol was analyzed using a chiral column (CHIRALPAK (registered trademark) AY-RH (Daicel), 4.6 mm × 150 mm, 5 μm, detector: 220 nm) at a column temperature of 35 °C, a mobile phase flow rate of 1 mL / min (5 mM ammonium acetate aqueous solution / MeCN = 400 / 600 (v / v)), a holding time of 3.3 min, and an optical purity of 80% ee. Furthermore, the retention time of the other optical isomer was 3.1 min.

[0208] Preparation of Intermediate Example 1-2 Preparation of 2-(4-(tri-butyl)phenyl)-3,3-dimethyloxocyclopropane-2-carboxylic acid (compound number E-1a): A solution of (2-(4-(tri-butyl)phenyl)-3,3-dimethyloxocyclopropane-2-yl)methanol (0.32 g, 1.3 mmol) in acetonitrile / water (6.8 mL / 0.40 mL) was prepared as described in Preparation of Intermediate Example 1-1. Ruthenium(III) chloride (61 mg, 0.29 mmol) and an aqueous solution of sodium periodate (0.85 g, 4.0 mmol) were added, and the mixture was stirred overnight at room temperature. The reaction was stopped by adding a saturated aqueous solution of sodium thiosulfate to the reaction solution. The mixture was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 2-(4-(tributyl)phenyl)-3,3-dimethyloxocyclopropane-2-carboxylic acid (0.29 g, 1.2 mmol). Yield: 92%. Properties: 1H-NMR (CDCl3): δ 7.51 (d, 2H), 7.35 (d, 2H), 1.54 (s, 3H), 1.31 (s, 9H), 1.10 (s, 3H).

[0209] Reference Manufacturing Example 1: Preparation of 2-(4-(tributyl)phenyl)-3-methyl-2-buten-1-ol: A solution of 2-bromo-3-methyl-2-buten-1-ol (6.0 g, 36 mmol) in water (15 mL) and 1,4-dioxane (60 mL) was added sequentially, followed by the addition of 4-tributylphenylboronic acid (9.1 g, 51 mmol), SPhos (1.5 g, 3.6 mmol), tripotassium phosphate (15 g, 73 mmol), and tris(dibenzylacetone)dipalladium (0) (1.7 g, 1.8 mmol). The mixture was stirred at 116 °C for 3 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate and washed with saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was purified by silicone column chromatography to obtain 2-(4-(tributyl)phenyl)-3-methyl-2-buten-1-ol (5.0 g, 23 mmol). Yield: 63%. Properties: 1H-NMR (CDCl3): δ 7.35 (d, 2H), 7.11 (d, 2H), 4.42 (s, 2H), 1.91 (s, 3H), 1.64 (s, 3H), 1.33 (s, 9H).

[0210] Reference Manufacturing Example 2 Manufacturing of 2-(4-(2,2-dimethylpropyl)phenyl)oxocyclopropane-3,3-dimethyl-2-carboxynitrile Reference Manufacturing Example 2-1 Manufacturing of 2-bromo-1-(4-(2,2-dimethylpropyl)phenyl)-2-methylpropane-1-one Aluminum chloride (2.2 g, 16 mmol) was suspended in a solution of dichloromethane (15 mL), 2-bromoisobutyl bromide (1.5 g, 8.1 mmol) was added, and the mixture was stirred at 0 °C. Then, neopentylbenzene (1.5 g, 9.7 mmol) was added, and the mixture was stirred at 0 °C for 1.5 hours. The reaction mixture was poured into ice water and extracted with dichloromethane. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 2-bromo-1-(4-(2,2-dimethylpropyl)phenyl)-2-methylpropane-1-one (2.4 g, 8.1 mmol). Yield: 100%. Properties: 1H-NMR (CDCl3): δ 8.08 (d, 2H), 7.19 (d, 2H), 2.55 (s, 6H), 0.92 (s, 9H).

[0211] Reference Manufacturing Example 2-2: Preparation of 2-(4-(2,2-dimethylpropyl)phenyl)oxocyclopropane-3,3-dimethyl-2-carboxylonitrile 2-bromo-1-(4-(2,2-dimethylpropyl)phenyl)-2-methylpropane-1-one (2.4 g, 8.1 mmol) was dissolved in THF (4.0 mL) and water (4.0 mL), and tetrabutylammonium bromide (0.26 g, 0.81 mmol) and sodium cyanide (0.58 g, 12 mmol) were added. After stirring at room temperature for 2 hours, the reaction solution was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silicone column chromatography to obtain 2-(4-(2,2-dimethylpropyl)phenyl)oxocyclopropane-3,3-dimethyl-2-carboxylonitrile (1.7 g, 6.9 mmol). Yield: 85% Physical properties: 1H-NMR (CDCl3): δ 7.32 (d, 2H), 7.17 (d, 2H), 2.51 (s, 2H), 1.75 (s, 3H), 1.10 (s, 3H), 0.90 (s, 9H)

[0212] Hereinafter, examples of formulations comprising the compounds of the present invention are disclosed, but the present invention is not limited to such formulations. In the formulation examples, parts refer to parts by weight.

[0213] Formulation Example 1. A mixture of 10 parts xylene, 70 parts N-methylpyrrolidone, 10 parts polyoxyethylene nonylphenyl ether and alkylbenzene sulfonate calcium, or more, is uniformly mixed and dissolved to form an emulsion.

[0214] Formulation Example 2. The compound of the present invention is uniformly mixed and pulverized into a powder by mixing 3 parts of clay powder, 82 parts of clay powder, and 15 parts or more of diatomaceous earth powder.

[0215] Formulation Example 3. Five parts of the compound of the present invention, 90 parts of a mixed powder of bentonite and clay, and five or more parts of calcium lignosulfonate are uniformly mixed, and an appropriate amount of water is added to knead, granulate, and dry to form granules.

[0216] Formulation Example 4. A mixture of 20 parts of the compound of the present invention, 75 parts of synthetic highly dispersed silica, 5 parts of polyoxyethylene nonylphenyl ether, and alkylbenzene sulfonate calcium is uniformly mixed and pulverized to form a hydrating agent.

[0217] Formulation Example 5. 10 parts of the compound of the present invention, 5 parts of a nonionic / anionic surfactant mixture ("Sorpol 3105" (manufactured by Toho Chemical Co., Ltd.)), 2 parts of propylene glycol, 1 part of xanthan gum, and 82 parts of water. Preparation method: The components other than water are uniformly mixed and dispersed in water to form a flow agent.

[0218] Next, experimental examples of the present invention are disclosed, but are not limited to such examples.

[0219] Experiment 1. Test on the control effect of black spot disease of Chinese cabbage. The compound of the present invention, according to the formulation prepared according to Formulation Example 1, was diluted with water to the specified amount. 10 mL of the solution was scattered on the stems and leaves of Chinese cabbage (variety: Wushuang) cultivated in pots with a diameter of 5 cm to the 3 to 5 leaf stage. After the solution was air-dried, a spore suspension of the Chinese cabbage black spot pathogen was sprayed on it. After being kept at a temperature of 20°C and high humidity for 1 day, it was moved to a greenhouse to induce disease. The control effect was determined 5 days after inoculation according to the following criteria. [Number 1] Prevention efficacy (%) = (Average disease area ratio in untreated areas – Average disease area ratio in treated areas) × 100 Average morbidity rate in untreated areas

[0220] Judgment Criteria: 0: Control efficacy below 9%; 1: Control efficacy 10-19%; 2: Control efficacy 20-29%; 3: Control efficacy 30-39%; 4: Control efficacy 40-49%; 5: Control efficacy 50-59%; 6: Control efficacy 60-69%; 7: Control efficacy 70-79%; 8: Control efficacy 80-89%; 9: Control efficacy 90-99%; 10: Control efficacy 100%.

[0221] In the above-mentioned test results and the compounds of general formula [I] of the present invention, compounds A-1, A-6, A-7, A-14, A-15, A-16, A-19, A-26, A-40, A-42, A-43, A-47, A-49, A-51, A-53, A-54, A-55, A-59, A-65, A-70, A-72, A-83, A-85, A-88 and A-90 showed a control effect of criterion 8 or above at 50 ppm.

[0222] Experimental Example 2. Test on the control effect of tomato blight. The compound of the present invention, according to the formulation prepared according to Formulation Example 1, was diluted with water to the specified amount. 10 mL of the solution was scattered on the stems and leaves of tomatoes (variety: Momotaro) grown in pots with a diameter of 9 cm to the 3-4 leaf stage. After the solution was air-dried, a suspension of wandering soocysts of tomato blight pathogens was sprayed on the plants. After being kept at a temperature of 20°C and high humidity for 1 day, the plants were moved to a greenhouse to induce disease. The control effect was determined 5 to 6 days after inoculation according to the judgment criteria of Experimental Example 1.

[0223] Based on the above test results, among the compounds of general formula [I] of the present invention, compound A-2 showed a control effect of criterion 8 or higher at 200 ppm.

[0224] Example 3. Test on the control effect of cucumber gray mold. The compound of the present invention, represented by general formula [I], was prepared according to formulation example 1 and diluted with water to the specified amount. 10 mL of the solution was scattered on the stems and leaves of cucumbers (variety: four-leaf) cultivated in pots with a diameter of 9 cm to the one-leaf stage. After the solution was air-dried, a paper plate was placed in the center of the leaf to infect the spore suspension of cucumber gray mold. The condition was maintained at a temperature of 15°C and humidity to induce disease. The control effect was determined 5 to 6 days after inoculation according to the judgment criteria of Example 1.

[0225] Based on the above test results, among the compounds of general formula [I] of the present invention, compounds A-1, A-3, A-4, A-7, A-11, A-14, A-14b, A-15, A-16, A-17, A-18, A-19, A-20, A-37, A-38, A-39, A-42, A-43, A-45, A-47, A-48, A-50, A-51, A-52, A-53, A-54, A-55, A-64, A-65, A-68, A-69, A-70, A-72, A-73, A-74, A-80, A-81, A-82, A-87, A-89 and A-90 showed a control effect of at least 8 based on the judgment standard at 50 ppm.

[0226] Example 4. Test on the control effect of cucumber anthracnose. The compound of the present invention, according to the formulation of Example 1, was diluted with water to the specified amount. 10 mL of the solution was spread on the stems and leaves of cucumbers (variety: four-leaf) cultivated in pots with a diameter of 9 cm to the two-leaf stage. After the solution was air-dried, a suspension of cucumber anthracnose spores was sprayed on the plant. After being kept at 20°C and high humidity for 1 day, the plant was moved to a greenhouse to induce disease. The control effect was determined 6 days after inoculation according to the judgment criteria of Example 1.

[0227] According to the above test results, among the compounds represented by the general formula [I] of the present invention, A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-11, A-1 4. A-14b, A-15, A-16, A-18, A-19, A-22, A-23, A-24, A-25, A-26, A-27, A-40, A-43, A Compounds A-48, A-49, A-51, A-52, A-53, A-55, A-56, A-57, A-61, A-62, A-65, A-66, A-68, A-70, A-71, A-72, A-74, A-82, A-83, A-85, A-86, A-87, and A-90 exhibit a control effect of at least 8% at 50 ppm, which is considered a threshold of 8.

[0228] Example 5. Test on the control effect of rice blast disease. The compound of the present invention, according to the formulation prepared according to Formulation Example 1, was diluted with water to the specified amount. 10 mL of the solution was spread on the stems and leaves of rice (variety: Jin Nanfeng) cultivated in pots with a diameter of 6 cm to the 6-7 leaf stage. After the solution was air-dried, a suspension of spores of rice blast fungus was sprayed on it. After being kept at a temperature of 20°C and high humidity for 1 day, the plants were moved to a greenhouse to induce disease. The control effect was determined 6 days after inoculation according to the judgment criteria of Example 1.

[0229] Based on the above test results, among the compounds represented by the general formula [I] of the present invention, compounds A-1, A-2, A-3, A-5, A-14, A-14b, A-18, A-20, A-23, A-25, A-26, A-27, A-37, A-38, A-39, A-40, A-42, A-43, A-44, A-45, A-46, A-47, A-51, A-52, A-53, A-54, A-61, A-64, A-70, A-81, A-86, A-87 and A-88 showed a control effect of at least 5% at 50 ppm, which is considered to be above the standard 5.

[0230] Example 6. Test on the control effect of apple black spot disease. The compound of the present invention, according to the formulation of Example 1, was diluted with water to the specified amount. 10 mL of the solution was spread on the stems and leaves of apple seedlings (variety: Wanglin) cultivated in pots with a diameter of 5 cm. After the solution was air-dried, a spore suspension of the apple black spot pathogen was sprayed on the seedlings. After being kept at a temperature of 20°C and high humidity for 2 days, the seedlings were moved to an indoor environment at a temperature of 15°C and appropriately humidified to promote disease development. The control effect was determined 15 days after inoculation according to the judgment criteria of Example 1.

[0231] The above test results, among the compounds represented by the general formula [I] of the present invention, A-1, A-3, A-4, A-5, A-6, A-7, A-8, A-11, A-14, A-14b, A-15, A-16, A-17, A-18 , A-19, A-20, A-22, A-23, A-24, A-25, A-26, A-27, A-39, A-40, A-42, A-43, A-44, A-45, A-47, A-48, A-49, A-50, A Compounds A-51, A-52, A-54, A-55, A-56, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-68, A-69, A-70, A-71, A-72, A-73, A-74, A-79, A-80, A-81, A-82, A-83, A-84, A-85, A-86, A-87, A-88, A-89, and A-90 exhibit a control effect of at least 8% at 50 ppm, which is considered a threshold of 8.

[0232] Example 7. Test on the control effect of barley powdery mildew. The compound of the present invention, according to the formulation prepared according to Formulation Example 1, was diluted with water to the specified amount. 10 mL of the solution was scattered on the stems and leaves of barley (variety: Kanto 6) cultivated in pots with a diameter of 5 cm to the 1-leaf stage. After the solution was air-dried, barley powdery mildew pathogens were sprinkled on top for inoculation. The plants were kept in a greenhouse at a temperature of 25°C to promote disease development. The control effect was determined 7 days after inoculation according to the judgment criteria of Example 1.

[0233] Based on the above test results, among the compounds of general formula [I] of the present invention, compounds A-14, A-56 and A-65 showed a control effect of criterion 3 or higher at 50 ppm.

[0234] Example 8. Antimicrobial activity test: The following (a), (b) and (c) bacteria were used as test bacteria. PDA medium was used to confirm the inhibitory activity of each test compound on mycelial growth. After proliferation, the colony diameter was measured, and the half effective concentration (EC50: ppm) was calculated. (a) *Septoria tritici* (wheat leaf spot pathogen) (b) *Fusarium graminearum* (c) *Sclerotinia sclerotiorum*

[0235] The above test results list compounds with a half-maximal effective concentration (WOC) of 50 ppm or less. (a) A-1, A-2, A-3, A-6, A-7, A-10, A-11, A-12, A-13, A-14, A-14a, A-14b, A-15, A-17, A-18, A-19, A-21, A-22, A-23, A-26, A-27, A-41, A-43, A-47, A-49, A-63, A-64, A-70, A-72, A-80, A-81, A-85, A-86 and A-88 (b) A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-10, A-11, A-12, A-13, A-14, A-14a, A-14 b. A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-25, A-26, A-27, A-37, A-38, A-39, A-41, A-42, A-43, A-45, A-47, A-48, A-49, A-54, A-56, A-57, A-59, A- 64. A-65, A-67, A-69, A-70, A-72, A-76, A-77, A-80, A-81, A-83, A-85, A-86 and A-88 (c) A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-10, A-11, A-12, A-13, A-14, A-1 4a, A-14b, A-15, A-17, A-18, A-19, A-21, A-22, A-23, A-24, A-25, A-26, A- 27. A-37, A-38, A-39, A-41, A-42, A-43, A-45, A-47, A-48, A-49, A-54, A-5 5. A-56, A-57, A-59, A-64, A-65, A-70, A-72, A-80, A-81, A-85, A-86 and A-88 [Industry-level availability]

[0236] Since the compound or its salt represented by general formula [I] of the present invention has the effect of preventing and controlling diseases occurring in cereals, fruit trees, vegetables, other crops and flowers, it can be used as a pesticide.

[0237] This application is based on Japanese Patent Application No. 2024-078550 filed on May 14, 2024, the contents of which are fully contained in this specification.

Claims

1. A compound of general formula [I] or a salt thereof, wherein R1 and R5 may be the same or different, each being (a1) a halogen atom; (a2) a cyano group; (a3) ​​a nitro group; (a4) a hydroxyl group; (a5) an amino group; (a6) a (C1-C6) alkyl group; (a7) a (C2-C6) alkenyl group; (a8) a (C2-C6) alkynyl group; (a9) a (C3-C6) cycloalkyl group; (a10) a halo(C1-C6) alkyl group; (a11) a halo(C2-C6) alkenyl group; (a12) a halo(C2-C6) alkynyl group; (a13) a halo(C3-C6) cycloalkyl group; (a14) a (C1-C6) alkoxy group; (a15) a (C3-C6) cycloalkoxy group; (a16) (C1-C6)alkoxy(C1-C6)alkoxy; (a17) (C3-C6)cycloalkyl(C1-C6)alkoxy; (a18) halo(C1-C6)alkoxy; (a19) halo(C3-C6)cycloalkoxy; (a20) halo(C1-C6)alkoxy(C1-C6)alkoxy; (a21) halo(C3-C6)cycloalkyl(C1-C6)alkoxy; (a22) (C1-C6)alkylthio; (a23) (C1-C6)alkylsulfinyl; (a24) (C1-C6)alkylsulfinyl; (a25) halo(C1-C6)alkylthio; (a26) halo(C1-C6)alkylsulfinyl; (a27) halo(C1-C6)alkylsulfinyl; (a28) Phenyl; (a29) A substituted phenyl group having 1 to 5 substituents independently selected from substituent group Y on the ring; (a30) Phenoxy; (a31) A substituted phenoxy group having 1 to 5 substituents independently selected from substituent group Y on the ring; (a32) Phenyl (C1-C6)alkoxy; (a33) A substituted phenyl (C1-C6)alkoxy group having 1 to 5 substituents independently selected from substituent group Y on the ring; (a34) Pyridyl; (a35) A substituted pyridyl group having 1 to 4 substituents independently selected from substituent group Y on the ring; (a36) Pyridyloxy; (a37) A substituted pyridyloxy group having 1 to 4 substituents independently selected from substituent group Y on the ring; (a38) Thiophene; (a39) Substituted thiophene group having 1 to 3 substituents independently selected from substituent group Y on the ring; (a40) thiazolyl; (a41) substituted thiazolyl group having 1 or 2 substituents independently selected from substituent group Y on the ring; (a42) naphthyl; (a43) substituted naphthyl group having 1 to 7 substituents independently selected from substituent group Y on the ring; (a44) pyridazinyl; (a45) substituted pyridazinyl group having 1 to 3 substituents independently selected from substituent group Y on the ring;(a46) Pyrimidinyl; or (a47) substituted pyrimidinyl group having 1 to 3 substituents independently selected from each of the substituent groups Y on the ring; or (a48) two adjacent R1 or two adjacent R5 groups combined to form a (C1-C6) alkylene group that can be independently substituted by 1 to 4 substituents from a halogen atom and a (C1-C6) alkyl group, wherein the substituent group Y is composed of (b1) halogen atom; (b2) cyano; (b3) nitro; (b4) amino; (b5) (C1-C6) alkyl; (b6) (C2-C6) alkenyl; (b7) (C2-C6) ynyl; (b8) (C3-C6) cycloalkyl; (b9) halo(C1-C6) alkyl; (b10) halo(C2-C6) alkenyl; (b11) (b12) Halo(C2-C6)alkynyl; (b13) Halo(C3-C6)cycloalkyl; (b14) (C1-C6)alkoxy; (b15) (C1-C6)alkylsulfinyl; (b16) (C1-C6)alkylsulfinyl; (b17) Halo(C1-C6)alkoxy; (b18) Halo(C1-C6)alkylsulfinyl; (b19) Halo(C1-C6)alkylsulfinyl; and (b20) Halo(C1-C6)alkylsulfinyl, where R2 and R3 may be the same or different, each representing (c1) hydrogen atom; (c2) (C1-C6) alkyl; or (c3) Halogen atoms, or R2 and R3 bonded together, including the bonded carbon atoms, form a 3- to 6-membered saturated aliphatic ring. R4 represents (d1) hydrogen atom; (d2) (C1-C6) alkyl; (d3) (C1-C6) alkoxy; (d4) (C2-C6) alkenyl; (d5) (C2-C6) alkynyl; (d6) (C3-C6) cycloalkyl; (d7) (C3-C6) cycloalkyl(C1-C6) alkyl; (d8) (C1-C6) alkoxy(C1-C6) alkyl; (d9) (C1-C6) alkylcarbonyl; or (d10) (C1-C6) alkoxycarbonyl. Ar1 and Ar2 may be the same or different, each representing (e1) phenyl; (e2) pyridyl; (e3) N-oxide pyridyl; (e4) naphthyl; (e5) Thiophene group; (e6) thiazolyl group; (e7) thiadiazolyl group; (e8) quinolinyl group; (e9) naphthidyl group; (e10) pyridazinyl group; (e11) pyrimidinyl group; or (e12) pyrazinyl group, where X represents (f1) oxygen atom; or (f2) sulfur atom, m represents 0, 1, 2, 3, 4 or 5, and n represents 0, 1, 2, 3, 4 or 5.

2. A compound or a salt thereof as claimed in claim 1, wherein R1 and R5 may be the same or different, each being (a1) a halogen atom; (a2) a cyano group; (a6) a (C1-C6) alkyl group; (a9) a (C3-C6) cycloalkyl group; (a10) a halo(C1-C6) alkyl group; (a14) a (C1-C6) alkoxy group; (a15) a (C3-C6) cycloalkoxy group; (a28) a phenyl group; (a29) a substituted phenyl group having 1 to 5 substituents independently selected from substituent group Y on the ring; (a30) a phenoxy group; or (a31) a substituted phenoxy group having 1 to 5 substituents independently selected from substituent group Y on the ring, or (a48-1) two adjacent R1 groups or two adjacent R5 groups combined to form a (C1-C6) alkyl group, wherein substituent group Y is composed of: (b1) Halogen atom; (b5) (C1-C6) alkyl; and (b13) (C1-C6) alkoxy, R2 and R3 may be the same or different, each being a (c1) hydrogen atom; or (c2) (C1-C6) alkyl, R4 being a (d1) hydrogen atom; or (d2) (C1-C6) alkyl, Ar1 and Ar2 may be the same or different, each being a (e1) phenyl; (e2) pyridinyl; (e3) N-oxypyridinyl; (e11) pyrimidinyl; or (e12) pyrazinyl, X being a (f1) oxygen atom, m being 0 or 1, and n being 0, 1, or 2.

3. A compound or a salt thereof as claimed in claim 1 or 2, wherein R1 and R5 may be the same or different, each being (a1) a halogen atom; (a2) a cyano group; (a6) a (C1-C6) alkyl group; (a9) a (C3-C6) cycloalkyl group; (a10) a halo(C1-C6) alkyl group; (a14) a (C1-C6) alkoxy group; (a15) a (C3-C6) cycloalkoxy group; (a28) a phenyl group; (a29) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group Y on the ring; (a30) a phenoxy group; or (a31) a substituted phenoxy group having 1 to 5 substituents independently selected from the substituent group Y on the ring, or (a48-1) two adjacent R1 groups or two adjacent R5 groups combined to form a (C1-C6) alkyl group, wherein the substituent group Y is composed of: (b1) Halogen atom; and (b5) (C1-C6) alkyl, R2 and R3 may be the same or different, each being (c1) hydrogen atom; or (c2) (C1-C6) alkyl, R4 being (d1) hydrogen atom; or (d2) (C1-C6) alkyl, Ar1 and Ar2 may be the same or different, each being (e1) phenyl; (e2) pyridinyl; (e3) N-oxide pyridinyl; (e11) pyrimidinyl; or (e12) pyrazinyl, X being (f1) oxygen atom, m being 0 or 1, and n being 0, 1, or 2.

4. An agricultural and horticultural fungicide containing, as an active ingredient, any one of claims 1 to 3, a compound or a salt thereof.

5. A method for controlling plant diseases, which involves treating plants or soil with an effective amount of the agro-horticultural fungicide as described in claim 4.

6. Use of a compound or a salt thereof as described in any one of claims 1 to 3 as a bactericide.

7. A compound of general formula [II-2] or a salt thereof, wherein R1 represents (a1-2) an iodine atom; (a2) a cyano group; (a6-1) a (C2-C6) alkyl group; (a9) a (C3-C6) cycloalkyl group; (a10-1) a halo(C1-C6) alkyl group (excluding trifluoromethyl); (a14-1) a (C2-C6) alkoxy group; (a15) a (C3-C6) cycloalkoxy group; (a28) a phenyl group; (a29) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group Y on the ring; (a30) a phenoxy group; or (a31) a substituted phenoxy group having 1 to 5 substituents independently selected from the substituent group Y on the ring, or (a48-1) two adjacent R1 groups combined to form a (C1-C6) alkyl substituent group Y consisting of: (b1) Halogen atom; (b5) (C1-C6) alkyl; and (b13) (C1-C6) alkoxy, R2 and R3 may be the same or different, each representing (c1) hydrogen atom; or (c2) (C1-C6) alkyl, Ar1 represents (e1) phenyl; (e2) pyridinyl; (e3) N-oxide pyridinyl; (e11) pyrimidinyl; or (e12) pyrazinyl, m represents 1.

8. A compound or a salt thereof as claimed in claim 7, wherein R1 is (a1-2) an iodine atom; (a6-1) a (C2-C6) alkyl group; (a10-1) a halo(C1-C6) alkyl group (excluding trifluoromethyl); (a14-1) a (C2-C6) alkoxy group; (a15) a (C3-C6) cycloalkoxy group; (a28) a phenyl group; (a29) a substituted phenyl group having 1 to 5 substituents independently selected from substituent group Y on the ring; (a30) a phenoxy group; or (a31) a substituted phenoxy group having 1 to 5 substituents independently selected from substituent group Y on the ring, wherein substituent group Y is composed of: (b1) a halogen atom; (b5) a (C1-C6) alkyl group; and (b13) a (C1-C6) alkoxy group, and R2 and R3 may be the same or different, each being (c1) Hydrogen atom; or (c2) (C1-C6) alkyl, Ar1 is (e1) phenyl, and m is 1.