Pyridazinone compound or salt thereof and pest control agent containing it

Abstract

Over the years, despite the use of numerous pest control agents, there have been many challenges, such as pests developing resistance due to insufficient efficacy, thus limiting their use. Therefore, there is a desire to develop novel pest control agents with fewer of these drawbacks. This invention relates to a pyridazinone compound represented by formula (I) or a salt thereof. [In the formula, each symbol is as described in the instruction manual], a pest control agent containing the compound, and a method of applying the compound to control pests.

Description

Technical field

[0001] The present invention relates to novel pyridazinone compounds or their salts and pest control agents containing them as active ingredients. [Prior Art]

[0002] Patent Document 1 describes a 4-(heterocyclic)pyridazinone compound. This compound has an alkyl group, cycloalkyl group, or the like at the 2-position of the pyridazinone ring. If the compound represented by Formula (I) described below does not contain an aromatic ring at the same position, the two compounds have different chemical structures. Patent Documents 2 and 3 describe pyridazinone compounds. This compound has an alkyl group, cycloalkyl group, tetrahydropyranyl group, or the like at the 2-position of the pyridazinone ring. If the compound represented by Formula (I) described below does not contain an aromatic ring at the same position, the two compounds have different chemical structures. Patent Document 4 describes a pyridazinone compound. This compound has AR 3 (A includes NR 4, R 4 represents a C 1-C 6 alkyl group, or can form a 5- or 6-membered ring together with R 3) at the 4-position of the pyridazinone ring. If the compound represented by Formula (I) described below does not contain a pyrazole or triazole at the same position, the two compounds have different chemical structures.

[0003] Patent Document 5 describes an antibacterial composition containing a pyridazinone compound. Patent Document 6 describes a 4-substituted pyridazinone compound and a c-Met inhibitor. Patent Document 7 describes a pyridazinone compound and a therapeutic drug for a proliferative disease. Patent Document 8 describes a pyridazinone compound and a P2X7 receptor inhibitor. However, in Patent Documents 5 to 8, there is no specific disclosure of compounds such as the compounds represented by formula (I) described below, wherein the 2-position of the pyridazinone ring is an aromatic ring and the 4-position of the pyridazinone ring is a pyrazole or triazole. In addition, there is no disclosure of the control of agricultural and horticultural pests or animal parasites. [Prior Art Documents] [Patent Documents]

[0004] [Patent Document 1] International Publication No. 2011 / 045271 [Patent Document 2] International Publication No. 2009 / 086041 [Patent Document 3] Japanese Patent Application Publication No. 2012-56903 [Patent Document 4] Japanese Patent Application Publication No. 63-185966 [Patent Document 5] International Publication No. 2015 / 143164 [Patent Document 6] International Publication No. 2008 / 103277 [Patent Document 7] International Publication No. 2008 / 080056 [Patent Document 8] International Publication No. 2010 / 126104 [Summary of the invention]

[0005] [Problems to be solved by the invention]

[0006] Although many pest control agents have been used for many years, their effectiveness is still insufficient, and pests and the like may acquire resistance, which limits their use. Therefore, the development of novel pest control agents with fewer of these drawbacks is desired. The present invention aims to provide a compound that is highly active against pests, a pest control agent containing the compound, and a method for applying the compound to control pests. [Means for Solving the Problems]

[0007] The present inventors conducted various studies on pyridazinone compounds in order to discover a more excellent pest control agent. As a result, they discovered a novel diaryl pyridazinone compound having an aromatic ring at the 2-position of the pyridazinone ring and a pyrazole or triazole bonded to the 4-position of the pyridazinone ring through its nitrogen atom. The pyridazinone compound represented by formula (I) or its salt has a pest control effect, thereby completing the present invention. That is, the present invention relates to a pyridazinone compound represented by formula (I) or its salt,

[0008] (wherein, Q is Q1, Q2, Q3 or Q4;

[0009] X is CH, C(R)A or N; Y and R are independently halogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, hydroxy, cyano, nitro, -SF5, -NRBRC, -C(=O)RD or -C(=O)NRERF; Z is alkyl, alkenyl, alkynyl, cycloalkyl, alkoxyalkyl, cycloalkylalkyl or haloalkyl; R1, R2, R3 and R4 are independently halogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxy, cycloalkyloxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, hydroxy, cyano, nitro, -NRGR (H, -C(=O)RI, -C(=O)NR JR K, -C(=NOR L)RM, dimethoxymethyl, 1,3-dioxan-2-yl or 1,3-dioxolan-2-yl; RB, RC, RE, RF, RG, RH, RJ and RK are independently a hydrogen atom, an alkyl group or a haloalkyl group; RD and RI are independently a hydrogen atom, a hydroxyl group, an alkyl group, a haloalkyl group or an alkoxy group; RL and RM are independently a hydrogen atom or an alkyl group; n is an integer from 0 to 4; a is an integer from 0 to 3; b, c and d are independently 0, 1 or 2).

[0010] The present invention also relates to a pest control agent containing a pyridazinone compound represented by the aforementioned formula (I) or a salt thereof as an active ingredient, and to a method for controlling the unwanted organisms by applying a pest control-effective amount of the compound or salt thereof to unwanted organisms or a location where the unwanted organisms are grown. [Effects of the Invention]

[0011] The pyridazinone compound represented by the aforementioned formula (I) or its salt has an effect of controlling pests. [Implementation Method] Examples of the halogen atom or halogen atom of the substituent in formula (I) include fluorine, chlorine, bromine, or iodine. The number of halogen atoms serving as the substituent may be 1 or 2 or more. When the number is 2 or more, the halogen atoms may be the same or different. Furthermore, the halogen atom may be substituted at any position. Examples of the alkyl group or alkyl moiety in formula (I) include a linear or branched carbon group having 1 to 5 carbon atoms (C1-C5) such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, or neopentyl. In particular, the alkyl group or alkyl moiety of Z in formula (I) is preferably a linear or branched carbon group having 1 to 4 carbon atoms (C1-C4), more preferably a methyl, ethyl, isopropyl, or tert-butyl group.

[0014] As examples of the alkoxy group or alkoxy moiety in the aforementioned formula (I), there can be mentioned a linear or branched carbon number 1 to 4 (C1-C4) group such as methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy.

[0015] Examples of the alkenyl group in the aforementioned formula (I) include ethenyl, 1-propenyl, 2-propenyl, isopropenyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl, 2-methyl-2-propenyl, 1-methyl-2-propenyl, 1-butenyl, 2-butenyl, and 3-butenyl groups having a linear or branched carbon number of 2 to 4 (C2-C4) and at least one double bond at any position.

[0016] Examples of the alkynyl group in the aforementioned formula (I) include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, or 1-methyl-2-propynyl, which are linear or branched groups having 2 to 4 carbon atoms (C2-C4) and having at least one triple bond at any position. Examples of the cycloalkyl group or cycloalkyl moiety in formula (I) include a group having 3 to 6 carbon atoms (C3-C6) such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. In particular, the cycloalkyl group or cycloalkyl moiety of Z in formula (I) is preferably a group having 3 to 6 carbon atoms (C3-C6), more preferably a group having 3 to 4 carbon atoms (C3-C4), such as cyclopropyl or cyclobutyl.

[0018] As the cycloalkoxy group in the aforementioned formula (I), for example, a group having 3 to 6 carbon atoms (C3-C6) such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy can be mentioned. In the aforementioned formula (I), when n is an integer greater than or equal to 2, each substituent Y may be the same or different. Similarly, when a is an integer greater than or equal to 2, each substituent R1 may be the same or different. Similarly, when b, c, or d is 2, each substituent R2, R3, and R4 may be the same or different.

[0020] In the aforementioned formula (I), since Q is represented by Q 1 to Q 4, the compound of formula (I) is specifically represented by the following formulas (i) to (iv).

[0021]

[0022] The compound of the aforementioned formula (i) includes compounds of the following formulas (ia) to (ih) depending on the number and position of the substituents on Q1.

[0023]

[0024] Similarly, the compound of the aforementioned formula (ii) includes compounds of the following formulas (ii-a) to (ii-c) depending on the number and position of the substituents in Q2.

[0025]

[0026] Similarly, the compound of the aforementioned formula (iii) includes compounds of the following formulas (iii-a) to (iii-d) depending on the number and position of the substituents in Q 3.

[0027]

[0028] Similarly, the compound of the aforementioned formula (iv) includes compounds of the following formulas (iv-a) to (iv-d) depending on the number and position of the substituents in Q4.

[0029] In addition, the symbols in the compounds of Formulas (i) to (iv), (ia) to (ih), (ii-a) to (ii-c), (iii-a) to (iii-d), and (iv-a) to (iv-d) have the same meanings as those in Formula (I). Furthermore, the description of the compound of Formula (I) in this specification also includes the description of the compounds of the aforementioned formulae included in Formula (I).

[0031] As the compound represented by formula (i), preferably, a compound represented by formula (ia), formula (ic), formula (id), or formula (ig), more preferably, a compound represented by formula (ic), formula (id), or formula (ig). As the compound represented by formula (ii) to (iv), preferably, a compound represented by formula (ii-a), formula (ii-b), formula (ii-c), formula (iii-a), formula (iii-c), formula (iv-a), or formula (iv-c), more preferably, a compound represented by formula (ii-b), formula (ii-c), formula (iii-c), or formula (iv-c). In formula (I), Q is preferably Q 1 or Q 3, that is, preferably, a compound represented by the aforementioned formula (i) or formula (iii). Furthermore, the compound represented by formula (i) or formula (iii) is preferably a compound represented by formula (ia), formula (ic), formula (id), formula (ig), formula (iii-a) or formula (iii-c), and more preferably a compound represented by formula (ic), formula (id), formula (ig) or formula (iii-c).

[0032] As salts of the compound of the aforementioned formula (I), if they are permitted in the technical field, including all, for example, alkali metal salts such as sodium salts and potassium salts; alkaline earth metal salts such as magnesium salts and calcium salts; quaternary alkylammonium salts such as tetrabutylammonium salts; amine salts such as dimethylamine salts and triethylamine salts; inorganic acid salts such as hydrochlorides, perchlorates, sulfates, and nitrates; organic acid salts such as acetates and methanesulfonates, etc.

[0033] Although there may be isomers such as diastereoisomers or optical isomers in the compound of the aforementioned formula (I) or its salt, the present invention includes both individual isomers and mixtures of isomers. In this specification, unless otherwise specified, isomers are described as mixtures. In addition, the present invention also includes various isomers other than the aforementioned isomers within the scope of technical common sense in the technical field. In addition, although there may be chemical structures different from the aforementioned general formula (I) depending on the type of isomer, those with ordinary knowledge in the field of the present invention will fully recognize that such chemical structures are isomers with the general formula (I), and therefore are clearly within the scope of the present invention. For example, the compound of the aforementioned formula (I) or its salt may contain the following tautomeric isomers.

[0034]

[0035] The compound of the aforementioned formula (I) or its salt (hereinafter also referred to as the compound of the present invention) can be produced according to the following production method or a conventional salt production method, but is not limited to such methods. For example, the compound (I) of the present invention is a substituent on the pyridazinone ring and the pyrazolyl, triazolyl, phenyl, or pyridyl group. In the art, it can also be produced by applying various substituent conversion reactions (such as alkylation reaction, haloalkylation reaction, cross-coupling reaction such as Suzuki coupling reaction, Sandmeyer type reaction, halogenation reaction, oxidation reaction, reduction reaction, etc.). In addition, if necessary, any functional group in the starting material or intermediate can be protected with a protecting group known in the art. Such protecting groups can be used by methods known in the art and can be removed at an appropriate stage in the reaction sequence. In the following production methods, although geometric isomers derived from carbon-nitrogen double bonds may exist in the chemical formula, the description below encompasses both individual geometric isomers and mixtures thereof in any proportion. For example, in the chemical formula, a wavy line indicates that all geometric isomers derived from carbon-nitrogen double bonds are included. Furthermore, the reaction can be carried out under an inert gas atmosphere such as nitrogen or argon, if necessary.

[0036] Preparation method [1] Among the compounds of formula (I), the compound of formula (Ia) wherein X is N can be prepared by sequentially reacting a compound of formula (II) with a compound of formula (III) to obtain a compound of formula (IV) in step 1, and reacting the compound of formula (IV) in the presence of a base in step 2.

[0037]

[0038] In the formula, Z1 is an alkyl group, and the other symbols are as described above. In step 1 of preparation method [1], a compound of formula (II) is reacted with a compound of formula (III) in the presence of a base to produce a compound of formula (IV). The compound of formula (III) is commercially available or can be produced according to known methods. Examples of the base include alkali metal hydrides such as sodium hydride; alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; and alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (II).

[0041] The reaction in step 1 of preparation method [1] can be carried out in the presence of a solvent if necessary. As a solvent, any solvent inert to the reaction may be used, although there is no particular limitation. For example, one or more solvents can be appropriately selected from ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aliphatic halogenated hydrocarbons such as dichloromethane, dichloroethane, and chloroform; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, dimethylsulfoxide, and cyclobutanesulfonate; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane; or a mixture thereof.

[0042] In step 1 of preparation method [1], the reaction temperature is about -20°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0043] In step 2 of preparation method [1], the compound of formula (IV) obtained in step 1 is reacted with a base to produce the compound of formula (Ia).

[0044] As the base, the same ones as those in the above-mentioned step 1 can be listed.

[0045] The reaction in step 2 of preparation method [1] can be carried out in the presence of a solvent if necessary. As a solvent, any solvent inert to the reaction may be used, although there is no particular limitation. For example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aliphatic halogenated hydrocarbons such as dichloromethane, dichloroethane, and chloroform; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, dimethylsulfoxide, and cyclobutanesulfonate; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane; water; etc. can be appropriately selected from one or more or a mixture thereof. The reaction temperature in step 2 of preparation method [1] is about -20°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0047] Intermediate Preparation [1-1] The compound of formula (II) can be prepared by reacting a compound of formula (V) with a compound of formula (VI) in the presence of a base. The compound of formula (VI) is commercially available or can be prepared according to known methods.

[0048]

[0049] In the formula, L is a halogen atom, and other symbols are as described above. Examples of the base include alkali metal hydrides such as sodium hydride; alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; and tertiary amines such as triethylamine, 4-methylmorpholine, and diisopropylethylamine. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (V). The reaction of the intermediate preparation method [1-1] can be carried out in the presence of a solvent, if necessary. Any solvent inert to the reaction may be used, and there is no particular limitation. However, one or more solvents, or a mixture thereof, can be appropriately selected from the same solvents as those in step 1 of the aforementioned preparation method [1]. The reaction temperature of the intermediate method [1-1] is about 0°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0053] Intermediate Preparation [1-2] The compound of formula (V) can be prepared according to the description in known literature (e.g., Protective Groups in Organic Synthesis Fourth Edition, John Wiley & Sons, Inc.). For example, the compound of formula (V) can be prepared by reacting the compound of formula (VII) in the presence of an acid.

[0054]

[0055] The symbols in the formula are as mentioned above.

[0056] As the acid, for example, inorganic acids such as hydrochloric acid; organic acids such as acetic acid, formic acid, and trifluoroacetic acid can be listed.

[0057] The reaction of the intermediate method [1-2] can be carried out in the presence of a solvent if necessary. Any solvent may be used as long as it is inert to the reaction. Although not particularly limited, for example, one or more solvents may be appropriately selected from ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aliphatic halogenated hydrocarbons such as dichloromethane, dichloroethane, and chloroform; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, dimethylsulfoxide, and cyclobutanesulfonate; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane; and ketones such as acetone and ethyl methyl ketone, or a mixture thereof. The reaction temperature of the intermediate method [1-2] is about 0°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0059] Intermediate Preparation [1-3] The compound of formula (VII) can be prepared by reacting a compound of formula (VIII) with a compound of formula (IX) in the presence of a metal catalyst and a base. The compound of formula (IX) is commercially available or can be prepared according to known methods.

[0060]

[0061] In the formula, the two Ras can each independently represent a hydrogen atom or can be the same or different (C1-C6) alkyl groups, or the two Ras can come together to form -CH2CH2- or -C(CH3)2C(CH3)2-. Other symbols are as described above.

[0062] Generally, any metal catalyst suitable for use in cross-coupling reactions is sufficient. Examples include palladium catalysts such as palladium-carbon, palladium chloride, palladium acetate, tetrakis(triphenylphosphine)palladium, bis(triphenylphosphine)palladium dichloride, and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride dichloromethane adduct; and copper catalysts such as metallic copper, copper(I) acetate, copper(II) acetate, copper(I) oxide, copper(II) oxide, and copper iodide.

[0063] As the base, for example, one or more of the following can be appropriately selected from tertiary amines such as triethylamine and diisopropylethylamine; alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; alkaline earth metal carbonates such as calcium carbonate and barium carbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide; alkali metal phosphates such as sodium phosphate and potassium phosphate; and alkaline earth metal phosphates such as calcium phosphate. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (VIII).

[0064] The reaction of the intermediate preparation method [1-3] can be carried out in the presence of a solvent if necessary. As a solvent, any solvent inert to the reaction can be used, although there is no particular limitation. For example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, dimethoxyethane; aliphatic halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; N,N-dimethylformamide, N,N- Aprotic polar solvents such as dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, dimethylsulfoxide, and cyclobutanesulfonate; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane; ketones such as acetone and ethyl methyl ketone; alcohols such as methanol, ethanol, and isopropyl alcohol; and water can be appropriately selected and used alone or in combination. The reaction temperature of the intermediate method [1-3] is about 20°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0066] Intermediate Preparation [1-4] The compound of formula (VIII) can be produced according to the description in known literature (e.g., Protective Groups in Organic Synthesis Fourth Edition, John Wiley & Sons, Inc.). For example, the compound of formula (VIII) can be produced by reacting a compound of formula (X) with 3,4-dihydro-2H-pyran in the presence of an acid. The compound of formula (X) is commercially available or can be produced according to known methods.

[0067]

[0068] As the acid, for example, organic acids such as methanesulfonic acid, trifluoroacetic acid, p-toluenesulfonic acid, and pyridinium p-toluenesulfonate can be listed.

[0069] The reaction of the intermediate method [1-4] can be carried out in the presence of a solvent if necessary. Any solvent may be used as long as it is inert to the reaction. Although not particularly limited, for example, one or more solvents may be appropriately selected from ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aliphatic halogenated hydrocarbons such as dichloromethane, dichloroethane, and chloroform; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, dimethylsulfoxide, and cyclobutanesulfonate; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate and ethyl propionate; and aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane, or a mixture thereof. The reaction temperature of the intermediate method [1-4] is about 10°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0071] Preparation method [2] The compound of the aforementioned formula (I) can be prepared by reacting a compound of the formula (XI) in the presence of a base.

[0072]

[0073] In the formula, R b is a (C 1-6) alkyl group, and other symbols are as described above.

[0074] Examples of the base include alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; alkaline earth metal carbonates such as calcium carbonate and barium carbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide; alkali metal hydrides such as sodium hydride; alkyl lithiums such as n-butyl lithium and tert-butyl lithium; metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, and potassium hexamethyldisilazane; metal alkoxides such as sodium methoxide and potassium tert-butoxide; tertiary amines such as triethylamine, 4-methylmorpholine, and diisopropylethylamine; 1,8-diazacyclo[5.4.0]-7-undecene, 1,4-diazacyclo[2.2.2]octane, pyridine, 4-(dimethylamino)pyridine, and 2,6-lutidine. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (XI). The reaction of preparation [2] can be carried out in the presence of a solvent, if necessary. Any solvent inert to the reaction may be used, and there is no particular limitation. However, one or more solvents, or a mixture thereof, can be appropriately selected from the same solvents as those described in the intermediate preparation [1-2].

[0076] The reaction temperature of preparation method [2] is about -20°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0077] Intermediate Preparation [2-1] The compound of formula (XI) can be prepared by reacting a compound of formula (XII) with a compound of formula (XIII) in the presence of an acid, if necessary. The compound of formula (XIII) is commercially available or can be prepared according to known methods, for example, according to the description in known literature (e.g., US2004087569A1 (page 6,

[0092] , page 7,

[0093] , etc.).

[0078]

[0079] The symbols in the formula are as mentioned above.

[0080] Examples of the acid include inorganic acids such as hydrochloric acid and sulfuric acid; and organic acids such as acetic acid, formic acid, methanesulfonic acid, trifluoroacetic acid, and p-toluenesulfonic acid.

[0081] The reaction of the intermediate method [2-1] can be carried out in the presence of a solvent if necessary. Any solvent may be used as long as it is inert to the reaction. Although not particularly limited, for example, one or more solvents may be appropriately selected from ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aliphatic halogenated hydrocarbons such as dichloromethane, dichloroethane, and chloroform; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, dimethylsulfoxide, and cyclobutanesulfonate; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane; and alcohols such as methanol, ethanol, and isopropyl alcohol, or a mixture thereof. The reaction temperature of the intermediate method [2-1] is about -20°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0083] Intermediate Preparation [2-2] The compound of formula (XII) can be prepared according to the description in known literature (e.g., Protective Groups in Organic Synthesis Fourth Edition, John Wiley & Sons, Inc.). For example, the compound of formula (XII) can be prepared by reacting the compound of formula (XIV) in the presence of an acid.

[0084]

[0085] The symbols in the formula are as mentioned above.

[0086] As the acid, for example, inorganic acids such as hydrochloric acid; organic acids such as trifluoroacetic acid; etc. can be listed.

[0087] The reaction of the intermediate preparation method [2-2] can be carried out in the presence of a solvent if necessary. As a solvent, any solvent inert to the reaction may be used, and although not particularly limited, for example, one or more solvents can be appropriately selected from ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aliphatic halogenated hydrocarbons such as dichloromethane, dichloroethane, and chloroform; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane, or a mixture thereof. The reaction temperature of the intermediate method [2-2] is about 0°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0089] Intermediate Preparation Method [2-3] The compound of formula (XIV) can be prepared by reacting a compound of formula (XV) with a compound of formula (XVI) in the presence of a base. The compound of formula (XVI) can be prepared using commercially available products or by the intermediate preparation method [2-6].

[0090]

[0091] The symbols in the formula are as mentioned above.

[0092] As the base, the same as those in the above-mentioned preparation method [2] can be mentioned. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (XV). The reaction of the intermediate method [2-3] can be carried out in the presence of a solvent if necessary. Any solvent inert to the reaction may be used, and there is no particular limitation. However, one or more solvents, such as those described in the intermediate method [1-2], can be appropriately selected or used in combination. The reaction temperature of the intermediate method [2-3] is about -20°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0095] Intermediate Preparation [2-4] The compound of formula (XV) can be prepared according to the description in known literature (e.g., Protective Groups in Organic Synthesis Fourth Edition, John Wiley & Sons, Inc.). For example, the compound of formula (XV) can be prepared by reacting the compound of formula (XVII) with a protecting agent such as di-tert-butyl dicarbonate ((Boc)2O) in the presence of a base, if necessary.

[0096]

[0097] The symbols in the formula are as mentioned above.

[0098] The reaction of the intermediate preparation method [2-4] can be carried out in the presence of a base if necessary. Examples of the base include alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; alkaline earth metal carbonates such as calcium carbonate and barium carbonate; alkali metal hydrides such as sodium hydride; tertiary amines such as triethylamine, 4-methylmorpholine, and diisopropylethylamine; 1,8-diazacyclo[5.4.0]-7-undecene and 4-(dimethylamino)pyridine.

[0099] The reaction of the intermediate preparation method [2-4] can be carried out in the presence of a solvent if necessary. As a solvent, any solvent inert to the reaction can be used, although there is no particular limitation. For example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aliphatic halogenated hydrocarbons such as dichloromethane, dichloroethane, and chloroform; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, dimethylsulfoxide, and cyclobutanesulfonate; esters such as ethyl acetate and ethyl propionate; water; etc. can be appropriately selected and used alone or in combination.

[0100] The reaction temperature of the intermediate preparation method [2-4] is about 0°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0101] Intermediate preparation method [2-5] In addition to using commercially available products, the compound of the formula (XVII) can also be prepared by reacting the compound of the formula (XVIII) with a nitrite such as sodium nitrite in an aqueous solution containing an acid, preparing the diazonium salt of the formula (XIX), and then reacting the prepared diazonium salt with a reducing agent in an aqueous solution containing an acid. The compound of the formula (XVIII) is commercially available or can be prepared according to known methods, for example, according to the description in known literature (for example, International Publication No. 2021 / 097057 (page 348, Step 1 to Step 3 of Intermediate A-7), etc.).

[0102]

[0103] In the formula, T- is chloride ion, sulfate ion, acetate ion and trifluoroacetic acid anion, and other symbols are as described above.

[0104] As the acid, for example, one or more kinds of inorganic acids such as hydrochloric acid and sulfuric acid, or organic acids such as acetic acid and trifluoroacetic acid, can be appropriately selected or mixed for use.

[0105] As reducing agents, tin (II) chloride and the like can be listed.

[0106] The reaction temperature of the intermediate method [2-5] is about -20°C to 100°C. The reaction time is about 0.5 hours to 24 hours.

[0107] Intermediate Method [2-6] The compound of formula (XVI) can be prepared by reacting a compound of formula (XX) with a halogenating agent. The compound of formula (XX) can be prepared using a commercially available product or by the intermediate method [2-7] or the intermediate method [2-9].

[0108]

[0109] The symbols in the formula are as mentioned above.

[0110] As halogenating agents, there are no particular restrictions, but examples thereof include sulfonyl chloride, ethylenediamine chloride, phosphorus oxychloride, sulfonyl chloride, phosphorus trichloride, phosphorus pentachloride, and the like. The reaction of the intermediate method [2-6] can be carried out in the presence of a solvent if necessary. Any solvent inert to the reaction may be used, and there is no particular limitation. However, one or more solvents, such as those described in the intermediate method [1-2], can be appropriately selected or used in combination.

[0112] The reaction temperature of the intermediate method [2-6] is about 0°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0113] Intermediate Preparation [2-7] The compound of the aforementioned formula (XX) can be prepared by hydrolyzing the compound of the formula (XXI) in the presence of a base.

[0114]

[0115] The symbols in the formula are as mentioned above. Examples of the base include alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; alkaline earth metal carbonates such as calcium carbonate and barium carbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; and alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (XXI).

[0117] The reaction of the intermediate preparation method [2-7] can be carried out in the presence of a solvent if necessary. As a solvent, any solvent inert to the reaction may be used, and although not particularly limited, for example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, dimethylsulfoxide, and cyclobutanesulfonate; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane; alcohols such as methanol, ethanol, and isopropyl alcohol; water; etc. can be appropriately selected from one or more solvents or a mixture thereof.

[0118] The reaction temperature of the intermediate method [2-7] is about 0°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0119] Intermediate Preparation Method [2-8] The compound of formula (XXI) can be prepared by reacting a compound of formula (XXII) with a compound of formula (III) in the presence of a base, in addition to using a commercially available product. The compound of formula (XXII) is commercially available.

[0120]

[0121] The symbols in the formula are as mentioned above.

[0122] Examples of the base include alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; alkaline earth metal carbonates such as calcium carbonate and barium carbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide; alkali metal hydrides such as sodium hydride; metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, and potassium hexamethyldisilazane; metal alkoxides such as sodium methoxide and potassium tert-butoxide; tertiary amines such as triethylamine, 4-methylmorpholine, and diisopropylethylamine; 1,8-diazacyclo[5.4.0]-7-undecene, 1,4-diazacyclo[2.2.2]octane, pyridine, 4-(dimethylamino)pyridine, and 2,6-lutidine. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (XXII).

[0123] The reaction of the intermediate preparation method [2-8] can be carried out in the presence of a solvent if necessary. As a solvent, any solvent inert to the reaction may be used, and although not particularly limited, for example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, dimethylsulfoxide, and cyclobutanesulfonate; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate and ethyl propionate; and the like can be appropriately selected from one or more solvents or a mixture thereof.

[0124] The reaction temperature of the intermediate method [2-8] is about 0°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0125] Intermediate Preparation [2-9] The compound of the aforementioned formula (XX) can be prepared by reacting a compound of the formula (XXIII) with a compound of the formula (III) in the presence of a base. The compound of the formula (XXIII) is commercially available.

[0126]

[0127] The symbols in the formula are as mentioned above. Examples of the base include alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; alkaline earth metal carbonates such as calcium carbonate and barium carbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide; alkali metal hydrides such as sodium hydride; metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, and potassium hexamethyldisilazane; and metal alkoxides such as sodium methoxide and potassium tert-butoxide. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (XXIII).

[0129] The reaction of the intermediate preparation method [2-9] can be carried out in the presence of a solvent if necessary. As a solvent, any solvent inert to the reaction may be used, and although not particularly limited, for example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, dimethylsulfoxide, and cyclobutanesulfonate; and water can be appropriately selected and used as one or more solvents or a mixture thereof.

[0130] The reaction temperature of the intermediate method [2-9] is about 20°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0131] Intermediate Preparation Method [2-10] The compound of the aforementioned formula (XIV) can be prepared by reacting a compound of the formula (XXIV) with a compound of the formula (III) in the presence of a base.

[0132]

[0133] The symbols in the formula are as mentioned above. The base may be the same as those described in the intermediate preparation method [2-8]. The base may be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (XXIV). The reaction of the intermediate method [2-10] can be carried out in the presence of a solvent if necessary. Any solvent inert to the reaction may be used, and there is no particular limitation. However, one or more solvents, such as those described in the intermediate method [2-8], can be appropriately selected or used in combination.

[0136] The reaction temperature of the intermediate method [2-10] is about 0°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0137] Intermediate Preparation [2-11] The compound of formula (XXIV) can be prepared by reacting a compound of formula (XV) with a compound of formula (XXV) in the presence of a base. The compound of formula (XXV) is commercially available.

[0138]

[0139] The symbols in the formula are as mentioned above.

[0140] As the base, the same ones as those in the above-mentioned preparation method [2] can be mentioned. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (XV). The reaction of the intermediate method [2-11] can be carried out in the presence of a solvent if necessary. Any solvent inert to the reaction may be used, and there is no particular limitation. However, one or more solvents, such as those described in the intermediate method [1-2], can be appropriately selected or used in combination.

[0142] The reaction temperature of the intermediate method [2-11] is about -20°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0143] Preparation method [3] The compound of the aforementioned formula (I) can be prepared by reacting a compound of the formula (XXVI) with a compound of the formula (XVI).

[0144]

[0145] The symbols in the formula are as mentioned above. The reaction of preparation [3] can be carried out in the presence of a base, if necessary. Examples of the base include the same bases as those described in preparation [2]. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (XXVI).

[0147] The reaction of preparation method [3] can be carried out in the presence of a solvent if necessary. As a solvent, any solvent inert to the reaction can be used, although there is no particular limitation. For example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, dimethoxyethane, etc.; aliphatic halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, etc.; N,N-dimethylformamide, N,N- Aprotic polar solvents such as dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, dimethylsulfoxide, and cyclobutanesulfonate; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane; ketones such as acetone and ethyl methyl ketone; nitroalkanes such as nitromethane and nitroethane; and the like can be appropriately selected and used alone or in combination.

[0148] The reaction temperature of preparation method [3] is about -20°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0149] Intermediate Preparation Method [3-1] The compound of the aforementioned formula (XXVI) can be prepared by reacting a compound of the formula (XVII) with a compound of the formula (XIII) in the presence of an acid, if necessary. The reaction of the intermediate preparation method [3-1] can be carried out in the same manner as the intermediate preparation method [2-1].

[0150]

[0151] The symbols in the formula are as mentioned above.

[0152] Examples of the acid include inorganic acids such as hydrochloric acid and sulfuric acid; and organic acids such as acetic acid, formic acid, methanesulfonic acid, trifluoroacetic acid, and p-toluenesulfonic acid.

[0153] In addition, the compound of formula (XXVI) can be manufactured according to the records in known literature (for example, Bioorganic and Medicinal Chemistry Letters, 2014, 24, 1944-1947, etc.).

[0154] Preparation method [4] Among the compounds of formula (I), the compound of formula (Ib) in which Z is an alkoxyalkyl group can be prepared by reacting a compound of formula (XXVII) with a compound of formula (XXVIII) in the presence of a base. The compound of formula (XXVIII) is commercially available or can be prepared according to a known method.

[0155]

[0156] In the formula, Z2 is an alkyl group, and other symbols are as described above.

[0157] As the base, the same ones as those in the above-mentioned intermediate preparation method [2-8] can be mentioned. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (XXVII).

[0158] The reaction of preparation [4] can be carried out in the presence of a solvent if necessary. As a solvent, any solvent inert to the reaction may be used, and there is no particular limitation. However, one or more solvents can be appropriately selected from the same solvents as those in step 1 of preparation [1], or a mixture thereof.

[0159] The reaction temperature of preparation method [4] is about 0°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0160] If necessary, the following base or water may be added to the reaction vessel during the reaction. The stirring time after the addition of the base is about 0.5 hours to 12 hours.

[0161] Examples of the additional base include those described in the intermediate preparation method [2-7]. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (XXVII). Alternatively, an excess amount relative to 1 equivalent of the compound of formula (XXVII) can be used.

[0162] Intermediate method [4-1] The compound of formula (XXVII) can be produced by reacting a compound of formula (XXIX) with a reducing agent. The compound of formula (XXIX) can be produced according to the respective methods and intermediate methods by replacing Z in formula (I) with -C(=O)ORb in the method [2] and the intermediate method [2-1] or the method [3] and the intermediate method [3-1].

[0163]

[0164] The symbols in the formula are as mentioned above.

[0165] As a reducing agent, although there is no particular limitation, for example, lithium aluminum hydride, diisobutylaluminum hydride, sodium bis(2-methoxyethoxy)aluminum hydride, sodium borohydride, lithium borohydride, borane-tetrahydrofuran complex, etc. can be listed.

[0166] The reaction of the intermediate preparation method [4-1] can be carried out in the presence of a solvent if necessary. As a solvent, any solvent inert to the reaction may be used, and although not particularly limited, for example, one or more solvents can be appropriately selected from halogenated hydrocarbons such as dichloromethane, chloroform, dichloroethane, trichloroethane, and carbon tetrachloride; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; hydrocarbons such as n-hexane and n-heptane; ethers such as diethyl ether, tert-butyl methyl ether, 1,4-dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; and alcohols such as methanol, ethanol, and isopropyl alcohol, or a mixture thereof. The reaction temperature of the intermediate method [4-1] is about -20°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0168] Preparation method [5] Among the compounds of formula (I), the compound of formula (Id) wherein Q is Qb can be prepared by reacting a compound of formula (Ic) with a compound of formula (XXX). The compound of formula (XXX) is commercially available or can be prepared according to a known method. The reaction of preparation method [5] can be carried out in the same manner as the intermediate preparation method [1-3].

[0169]

[0170] In the formula, Qa is Q1, Q2, Q3 or Q4 having at least one chlorine, bromine or iodine substituent on the ring, Qb is Q1, Q2, Q3 or Q4 having at least one Z2 substituent on the ring, and other symbols are as described above.

[0171] Preparation method [6] The compound of formula (Id) can also be prepared by reacting a compound of formula (Ic) with a compound of formula (XXXI) to obtain a compound of formula (Ie) in step 1, followed by step 2. The compound of formula (XXXI) is commercially available or can be prepared according to known methods.

[0172]

[0173] In the formula, Rd is a hydrogen atom or an alkyl group, Qc is Q1, Q2, Q3 or Q4 having at least one alkenyl group as a substituent on the ring, and other symbols are as described above.

[0174] The reaction in step 1 of preparation [6] can be carried out in the same manner as the aforementioned intermediate preparation [1-3].

[0175] In step 2 of preparation method [6], the compound of formula (Id) can be produced by reacting the compound of formula (Ie) obtained in step 1 in a hydrogen environment in the presence of a metal catalyst. Generally speaking, any metal catalyst suitable for reduction reactions can be used. Examples include palladium catalysts such as palladium-carbon and palladium hydroxide; nickel catalysts such as Raney nickel; and platinum catalysts such as platinum-carbon and platinum oxide.

[0177] The reaction in step 2 of preparation method [6] can be carried out in the presence of a solvent if necessary. Any solvent may be used as long as it is inert to the reaction. Although not particularly limited, for example, one or more solvents may be appropriately selected from ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aliphatic halogenated hydrocarbons such as dichloromethane, dichloroethane, and chloroform; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, dimethylsulfoxide, and cyclobutanesulfonate; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane; ketones such as acetone and ethyl methyl ketone; alcohols such as methanol, ethanol, and isopropyl alcohol; and water, or a mixture thereof.

[0178] The reaction temperature in step 2 of preparation [6] is about 20°C to 100°C. The reaction time is about 0.5 hour to 24 hours.

[0179] Preparation method [7] Among the compounds of the aforementioned formula (I), the compound of the formula (If) having a formyl group can be used as Y to react the compound of the formula (XXXII) with an oxidizing agent.

[0180]

[0181] In the formula, m is an integer from 0 to 3, and other symbols are the same as described above.

[0182] As oxidizing agents, for example, dimethylsulfoxide-activator, 2,2,6,6-tetramethylpiperidinyl 1-oxyl (Oxyl), 1,1,1-triacetyloxy-1,1-dihydro-1,2-benzoxazole (Benziodoxole)-3-(1H)-one, manganese dioxide, pyridinium chlorochromate, pyridinium dichromate, etc. can be listed.

[0183] In the case of oxidation by dimethylsulfoxide-activating agent, examples of the activating agent include acid anhydrides such as acetic anhydride and trifluoroacetic acid; acyl chlorides such as sulfoxide chloride and ethylenediamine chloride; chlorine, N-chlorosuccinimide, etc.

[0184] 2,2,6,6-tetramethylpiperidinyl 1-oxyl (Oxyl) can be used in a catalytic amount. In this case, as a reoxidant, for example, sodium hypochlorite, iodophenyl diacetate, etc. are used.

[0185] The reaction of preparation method [7] can be carried out in the presence of a solvent if necessary. As a solvent, any solvent inert to the reaction may be used, although there is no particular limitation. For example, one or more solvents can be appropriately selected from ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aliphatic halogenated hydrocarbons such as dichloromethane, dichloroethane, and chloroform; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane; ketones such as acetone and ethyl methyl ketone; and alcohols such as methanol, ethanol, and isopropyl alcohol, or a mixture thereof.

[0186] The reaction temperature of preparation method [7] is about -78°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0187] Intermediate Preparation Method [7-1] The compound of the aforementioned formula (XXXII) can be prepared by reacting the compound of the formula (Ig) with a reducing agent. The compound of the formula (Ig) can be prepared by the method of Preparation Method [2] or Preparation Method [3]. The reaction of Intermediate Preparation Method [7-1] can be carried out in the same manner as the aforementioned Intermediate Preparation Method [4-1].

[0188]

[0189] The symbols in the formula are as mentioned above.

[0190] As a reducing agent, although there is no particular limitation, for example, lithium aluminum hydride, diisobutylaluminum hydride, sodium bis(2-methoxyethoxy)aluminum hydride, sodium borohydride, lithium borohydride, borane-tetrahydrofuran complex, etc. can be listed.

[0191] Preparation method [8] Among the compounds of the aforementioned formula (I), the compound of the formula (Ih) having a cyano group can be used as Y to react the compound of the formula (XXXIII) with acetic anhydride.

[0192]

[0193] The symbols in the formula are as mentioned above.

[0194] The reaction of preparation method [8] can be carried out in the presence of a solvent if necessary. As a solvent, any solvent inert to the reaction may be used, although there is no particular limitation. For example, one or more solvents can be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, dimethylsulfoxide, and cyclobutanesulfonate; or a mixture thereof.

[0195] The reaction temperature of preparation method [8] is about 50°C to 200°C. The reaction time is about 0.5 hour to 24 hours.

[0196] If necessary, the base or solvent listed below may be added to the vessel in which the reaction is being carried out in the process of the preparation [8]. Alternatively, the mixture obtained after treatment or purification may be mixed with the base or solvent listed below. The stirring time after adding the base or solvent is about 0.5 hours to 12 hours.

[0197] Examples of the additional base include those described in the intermediate preparation method [2-7]. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (XXXIII). Alternatively, an excess amount relative to 1 equivalent of the compound of formula (XXXIII) can be used.

[0198] The solvent is not particularly limited, but for example, one or more solvents can be appropriately selected from ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane; alcohols such as methanol, ethanol, and isopropyl alcohol; water; or a mixture thereof.

[0199] Intermediate Preparation Method [8-1] The compound of formula (XXXIII) can be prepared by reacting the compound of formula (XXXIV) with hydroxylamine in the presence of a base. Hydroxylamine can be used as a hydroxylamine solution or a hydroxylamine salt.

[0200]

[0201] The symbols in the formula are as mentioned above.

[0202] Examples of hydroxylamine solutions include aqueous hydroxylamine solutions and hydroxylamine-ethanol mixed solutions. Examples of hydroxylamine salts include hydroxylamine hydrochloride and hydroxylamine sulfate. The base may be selected from, for example, tertiary amines such as triethylamine and diisopropylethylamine; alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; alkaline earth metal carbonates such as calcium carbonate and barium carbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide; and acetates such as sodium acetate and potassium acetate. The base may be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (XXXIV).

[0204] The reaction of the intermediate preparation method [8-1] can be carried out in the presence of a solvent if necessary. As a solvent, any solvent inert to the reaction may be used, and although not particularly limited, for example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aliphatic halogenated hydrocarbons such as dichloromethane, dichloroethane, and chloroform; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, dimethylsulfoxide, and cyclobutanesulfonate; alcohols such as methanol, ethanol, and isopropyl alcohol; water; etc. can be appropriately selected from one or more solvents or a mixture thereof.

[0205] The reaction temperature of the intermediate method [8-1] is about -20°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0206] If necessary, the following base or water may be added to the reaction vessel during the reaction. The stirring time after the addition of the base is approximately 5 minutes to 12 hours.

[0207] Examples of the additional base include those described in the intermediate preparation method [2-7]. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (XXXIV). Alternatively, an excess amount relative to 1 equivalent of the compound of formula (XXXIV) can be used.

[0208] Intermediate Preparation [8-2] The compound of formula (XXXIV) can be prepared by reacting a compound of formula (If) with a compound of formula (XXXV) or a compound of formula (XXXVI) in the presence of a base. Compounds of formula (XXXV) and (XXXVI) are commercially available or can be prepared according to known methods.

[0209]

[0210] The symbols in the formula are as mentioned above.

[0211] Examples of the base include the same ones as those described in the intermediate preparation method [2-8]. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (If). The reaction of the intermediate preparation method [8-2] can be carried out in the presence of a solvent if necessary. As a solvent, any solvent inert to the reaction can be used, and there is no particular limitation. However, one or more solvents can be appropriately selected from the same solvents as those in step 1 of the above preparation method [1], or a mixture thereof.

[0213] The reaction temperature of the intermediate method [8-2] is about -20°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0214] Preparation method [9] Among the compounds of formula (I), the compound of formula (Ii) having an alkylsulfinyl group, an alkylsulfonyl group, a haloalkylsulfinyl group, or a haloalkylsulfonyl group as Y can be prepared by reacting a compound of formula (Ij) with an oxidizing agent. The compound of formula (Ij) can be prepared by the method of preparation method [1] and intermediate preparation methods [1-1] to [1-4], preparation method [2] and intermediate preparation methods [2-1] to [2-11], or preparation method [3] and intermediate preparation method [3-1].

[0215]

[0216] In the formula, Re is an alkyl group or a haloalkyl group, e is 1 or 2, and other symbols are as described above.

[0217] Examples of the oxidizing agent include peroxides such as hydrogen peroxide, peracetic acid, perbenzoic acid, and m-chloroperbenzoic acid. When hydrogen peroxide is used as the oxidizing agent, sodium tungstate or the like may be added if necessary.

[0218] The reaction of preparation method [9] can be carried out in the presence of a solvent if necessary. Any solvent may be used as long as it is inert to the reaction. Although not particularly limited, for example, one or more solvents can be appropriately selected from ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aliphatic halogenated hydrocarbons such as dichloromethane, dichloroethane, and chloroform; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, dimethylsulfoxide, and cyclobutanesulfonate; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane; and water, or a mixture thereof.

[0219] The reaction temperature of preparation method [9] is about -20°C to 100°C. The reaction time is about 0.5 hours to 24 hours.

[0220] Preparation method

[10] The compound of the aforementioned formula (Ii) can also be prepared by reacting a compound of the formula (XXXVII) in the presence of a base.

[0221]

[0222] The symbols in the formula are as mentioned above.

[0223] Examples of the base include the same ones as those described in the intermediate preparation method [2-7]. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (XXXVII).

[0224] The reaction of preparation method

[10] can be carried out in the presence of a solvent if necessary. As a solvent, any solvent inert to the reaction may be used, although there is no particular limitation. For example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aliphatic halogenated hydrocarbons such as dichloromethane, dichloroethane, and chloroform; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, dimethylsulfoxide, and cyclobutanesulfonate; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane; alcohols such as methanol, ethanol, and isopropyl alcohol; water; etc. can be appropriately selected from one or more or a mixture thereof.

[0225] The reaction temperature of preparation method

[10] is about 0°C to 150°C. The reaction time is about 0.5 hours to 24 hours.

[0226] Intermediate Preparation Method [10-1] The compound of the aforementioned formula (XXXVII) can be prepared by reacting the compound of the formula (XXXVIII) with an oxidizing agent. The reaction of the intermediate preparation method [10-1] can be carried out in the same manner as the aforementioned preparation method [9].

[0227]

[0228] The symbols in the formula are as mentioned above.

[0229] Examples of the oxidizing agent include peroxides such as hydrogen peroxide, peracetic acid, perbenzoic acid, and m-chloroperbenzoic acid. When hydrogen peroxide is used as the oxidizing agent, sodium tungstate or the like may be added if necessary.

[0230] Intermediate Preparation Method [10-2] The compound of formula (XXXVIII) can be prepared by reacting a compound of formula (Ij) with a compound of formula (XXXV) or a compound of formula (XXXVI) in the presence of a base. The reaction of intermediate preparation method [10-2] can be carried out in the same manner as in intermediate preparation method [8-2].

[0231]

[0232] The symbols in the formula are as mentioned above. Examples of the base include alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; alkaline earth metal carbonates such as calcium carbonate and barium carbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide; alkali metal hydrides such as sodium hydride; metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, and potassium hexamethyldisilazane; metal alkoxides such as sodium methoxide and potassium tert-butoxide; tertiary amines such as triethylamine, 4-methylmorpholine, and diisopropylethylamine; 1,8-diazacyclo[5.4.0]-7-undecene, 1,4-diazacyclo[2.2.2]octane, pyridine, 4-(dimethylamino)pyridine, and 2,6-lutidine. The base can be used in an amount of 0.5 to 10 equivalents relative to 1 equivalent of the compound of formula (Ij).

[0234] Next, desirable aspects of the pest control agent containing the compound of the present invention are described below. The pest control agent containing the compound of the present invention is useful as an agent for controlling pests, mites, nematodes, or soil pests that are problematic in the agricultural and horticultural fields, that is, as an agricultural and horticultural insecticide, acaricide, nematocide, or soil pesticide. It is also useful as an agent for controlling animal parasites, that is, as an animal parasiticide.

[0235] Examples of the aforementioned pests that are problematic in the agricultural and horticultural fields include aphids (myzus persicae, cotton aphids, etc.), planthoppers (brown planthoppers, etc.), leafhoppers, scale insects, stink bugs, whiteflies (tobacco whitefly, etc.), thrips, grasshoppers, flower flies, scarab beetles, ants, diamondback moths, cabbage loopers, cutworms, codling moths, corn armyworms, tobacco budworms, gypsy moths, Agricultural pests include the corn borer, beet armyworm, Colorado flower beetle, yellow melon weevil, cotton boll weevil, cutworm, and cutworm moth; gastropods such as slugs and snails; sanitary pests such as house lice, cockroaches, houseflies, and mosquitoes; stored grain pests such as the wheat moth, green bean weevil, grain beetle, and ground beetle; clothing and household pests such as clothes moth, round bonito beetle, and termites; and others. Examples of the aforementioned mites that pose a problem in the agricultural and horticultural fields include plant parasitic mites such as the two-spotted spider mite, red spider mite, Kanzawa spider mite, citrus spider mite, European spider mite, polyphagous fine mite, Pitt's gall mite, and root mite; and house dust mites such as the putrescent tyrophagous mite, American dust mite, and South claw mite. Examples of the aforementioned nematodes that are problematic in the agricultural and horticultural fields include plant-parasitic nematodes such as Pratylenchus, cyst nematodes, root-rot nematodes, rice stem-tip nematodes, strawberry bud nematodes, and pine wood nematodes. Examples of the aforementioned soil pests that are problematic in the agricultural and horticultural fields include isopods such as woodlice and rough porcelain woodlice. Pest control agents containing the compounds of the present invention are suitable for controlling, among the above-mentioned pests, for example, Hemiptera, Thysanoptera, Coleoptera, Acari, Lepidoptera, and nematodes. They are particularly effective against Hemiptera and Acari. Specific examples of these pests and nematodes include the following.

[0237] Pests of the order Hemiptera include pea aphid (Acyrthosiphon pisum), thick-haired grass aphid (Tetraneura nigriabdominalis), sugarcane cotton aphid (Ceratovacuna lanigera), potato aphid (Aulacorthum solani), cabbage aphid (Brevicoryne brassicae), soybean aphid (Aphis glycines), potato aphid (Macrosiphum euphorbiae), corn aphid (Rhopalosiphum maidis), false cabbage aphid (Lipaphis erysimi), sorghum aphid (Melanaphis sacchari), beet aphid (Aphis fabae), large citrus aphid (Toxoptera citricida), rice aphid (Rhopalosiphum padi), light-tube tongue aphid (Brachycaudus helichrysi), peach aphid (Myzus persicae), and peach aphid (Hyalopterus Aphids (Aphididae), including the following: pruni), spiraea aphid (Aphis spiraecola), cotton apple aphid (Eriosoma lanigerum), lettuce aphid (Nasonovia ribisnigri), wool aphid (Aphis gossypii), apple aphid (Aphis pomi), long-horned wheat aphid (Sitobion avenae), plantain aphid (Dysaphis plantaginea); phylloxeridae, including the following: Daktulosphaira vitifoliae, thin-shelled pecan aphid (Phylloxera notabilis), American walnut aphid (Phylloxera devastatrix), and Russelae; hemlock aphid (Adelges tsugae), fir aphid (Aphrastasia pectinatae), and fir aphid (Adelges piceae) and other Adelgidae;Whiteflies (Aleyrodidae), including greenhouse whitefly (Trialeurodes vaporariorum), tobacco whitefly (Bemisia tabaci), tea whitefly (Aleurocanthus camelliae), ashwood whitefly (Pealius euryae), citrus whitefly (Dialeurodes citri), and citrus spiniferus; planthoppers (Delphacidae), including rice planthopper (Javesella pellucida), sugarcane planthopper (Perkinsiella saccharicida), whiteback planthopper (Sogatella furcifera), corn planthopper (Peregrinus maidis), brown planthopper (Nilaparvata lugens), gray planthopper (Laodelphax striatellus), and Tagosodes orizicolus; electric leafhopper (Recilia dorsalis), black-striped and black-tailed leafhopper (Nephotettix Leafhoppers (Cicadellidae), including the potato green leafhopper (Empoasca fabae), the white-winged brown leafhopper (Cofana spectra), the Taiwan black-tailed leafhopper (Nephotettix virescens), the tea green leafhopper (Empoasca onukii), the false black-tailed leafhopper (Nephotettix cincticeps), the small green leafhopper (Amrasca biguttula), and the corn yellow-winged leafhopper (Dalbulus maidis); leafhoppers (Aphrophoridae), including the yellow-headed leafhopper (Philaenus spumarius); and leafhoppers (Cercopidae), including the Mahanarva fimbriolata.Pentatomidae stink bugs such as the Oriental green rice stink bug (Nezara antennata), the Black rice stink bug (Scotinophara lurida), the Japanese two-star stink bug (Eysarcoris lewisi), the Brown rice stink bug (Halyomorpha halys), the Broad two-star stink bug (Eysarcoris ventralis), the Small Amber stink bug (Plautia stali), the Northern two-star stink bug (Eysarcoris aeneus), the Green rice stink bug (Nezara viridula), the White-spotted stink bug (Eysarcoris annamita), the Malayan Black stink bug (Scotinophara coarctata), the Brown stink bug (Euschistus heros), the South American leaf beetle (Dichelops melacanthus), the Red-banded stink bug (Piezodorus guildinii), and the North American rice stink bug (Oebalus pugnax); the Subterraneous stink bug (Scaptocoris castanea); Alydidae, including the Chinese rice stink bug (Leptocorisa chinensis), the wheat spider stink bug (Leptocorisa acuta), and the wasp stink bug (Riptortus clavatus); Coreidae, including the leaf stink bug (Leptoglossus australis) and the rice thorn stink bug (Cletus punctiger); Lygaeidae, including the long stink bug (Blissus leucopterus), the sugarcane long stink bug (Cavelerius saccharivorus), and the small-winged gourd long electric bug (Togo hemipterus); Stenotus rubrovittatus, Trigonotylus caelestialium, and the American meadow stink bug (Lygus lineolaris), Lygus rugulipennis, Stenodema calcarata, etc.Diaspididae, including Aonidiella aurantii, Pseudaulacaspis prunicola, Pseudaulacaspis pentagona, Abgrallaspis cyanophylli, Diaspidiotus perniciosus, and Unaspis yanonensis; Coccidae, including Ceroplastes rubens; Margarodidae, including Icerya purchasi and Icerya seychellarum; Pseudococcus calceolariae, Phenacoccus solenopsis, and Pseudococcus chinensis. comstocki), Pseudococcus longispinus, Phenacoccus solani, Planococcus kraunhiae, Planococcus citri, Brevennia rehi, etc.; Psyllidae, Bactericera cockerelli, Cacopsylla chinensis, Cacopsylla pyrisuga, Diaphorina citri, Trioza erytreae, Cacopsylla pyricola, etc.; Chrysanthemum stink bug (Corythucha marmorata), Cuckoo stink bug (Stephanitis pyrioides), pear-crowned stink bug (Stephanitis nashi), sycamore square-winged stink bug (Corythucha ciliata), etc.; temperate stink bug (Cimicidae), including temperate stink bug (Cimex lectularius), tropical stink bug (Cimex hemipterus), etc.; cicada (Cicadidae), including giant cicada (Quesada gigas);Reduviidae bugs, including the broad-spine stink bug (Triatoma rubrofasciata), the infesting cone bug (Triatoma infestans), the red stink bug (Rhodonius prolixus), and the dichotomous cone bug (Triatoma dimidiata).

[0238] Pests of the order Thysanoptera include rice thrips (Stenchaetothrips biformis), small yellow thrips (Scirtothrips dorsalis), tobacco thrips (Thrips tabaci), flower thrips (Frankliniella intonsa), western flower thrips (Frankliniella occidentalis), melon thrips (Thrips palmi), American thorny thrips (Echinothrips americanus), avocado thrips (Scirtothrips perseae), etc., which belong to the Thripidae family; and rice pipe thrips (Haplothrips aculeatus), etc., which belong to the Phlaeothripidae family.

[0239] Pests classified as Coleoptera include rice ironclad beetle (Dicladispa armigera), rice mudworm (Oulema oryzae), yellow melon beetle (Aulacophora femoralis), yellow striped leaf flea (Phyllotreta striolata), black horned mudworm (Oulema melanopus), Colorado flower beetle (Leptinotarsa ​​decemlineata), sweet potato flower beetle (Chaetocnema confinis), southern corn rootworm (Diabrotica undecimpunctata Mannerheim), tobacco flea beetle (Epitrix hirtipennis), black striped flower beetle (Laccoptera quadrimaculata), spotted cucumber leaf beetle (Diabrotica balteata), bean leaf beetle (Cerotoma trifurcata), rapeseed golden-headed flea beetle (Psylliodes chrysocephala), corn flea beetle (Chaetocnema pulicaria), flea beetle (Phyllotreta cruciferae), Diabrotica speciosa, Colaspis brunnea, Psylliodes punctulata, Diabrotica barberi, Epitrix cucumeris, Myochrous denticollis, Phyllotreta pusilla, Diabrotica virgifera virgifera, and Diabrotica virgifera zeae; and Carabidae, including Clivina impressifrons and Stenolophus lecontei.Scarabaeidae beetles, including the small bronze beetle (Anomala albopilosa), Holotrichia kiotonensis, the dark gill beetle (Holotrichia parallela), the black round beetle (Tomarus gibbosus), the bronze beetle (Anomala cuprea), the yellow beetle (Heptophylla picea), the multicolored beetle (Anomala rufocuprea), the Japanese beetle (Popillia japonica), the European beetle (Rhizotrogus majalis), the June beetle (Phyllophaga crinita), the Anxia beetle (Phyllophaga anxia), the Phyllophaga crassissima, and the Argentine beetle (Diloboderus abderus); the long-horned beetles (Anthriibidae), including the coffee beetle (Araecerus coffeae); the sweet potato ant beetle (Cylas formicarius) and other needle-mouthed weevils (Aponidae); bean weevils (Bruchidae) such as the mung bean weevil (Callosobruchus chinensis) and the Brazilian bean weevil (Zabrotes subfasciatus); and beetle subclasses (Scolytidae) such as the vertical pit tip-cutter (Tomicus piniperda) and the coffee berry borer (Hypothenemus hampei);Alfalfa leaf weevil (Hypera postica), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), West Indian sweet potato weevil (Euscepes postfasciatus), corn weevil (Sitophilus granarius), corn weevil (Sitophilus zeamais), rice weevil (Sitophilus oryzae), cucurbit rust weevil (Scepticus griseus), parasitic corn weevil (Sphenophorus venatus), palm weevil (Rhabdoscelus lineaticollis), common weevil (Scepticus uniformis), cotton boll weevil (Anthonomus grandis), cottonseed gray weevil (Eutinobothrus brasiliensis), southern corn long-beak weevil (Sphenophorus callosus), sugarcane weevil (Sphenophorus levis), Moray broad-beak weevil (Aracanthus mourei), soybean stem weevil (Sternechus subsignatus); Tenebrionidae, including the rice beetle (Alphitobius diaperinus), the grain beetle (Tribolium castaneum), and the mixed flour beetle (Tribolium confusum); Coccinellidae, including the potato beetle (Epilachna vigintioctomaculata) and the eggplant beetle (Epilachna vigintioctopunctata); Bostrychidae, including the grain borer (Rhizopertha dominica) and the brown flour borer (Lyctus brunneus); Ptinidae; Cerambycidae, including the pink-necked longhorn beetle (Aromia bungii), the white-spotted longhorn beetle (Anoplophora malasiaca), and the longhorn beetle (Migdolus fryanus);Elateridae, including Melanotus okinawensis, Melanotus legatus, Agriotes fuscicollis, Aeolus spp., Anchastus spp., Conoderus spp., Ctenicera spp., and Limonius spp.; Staphylinidae, including Paederus fuscipes; Dermestidae, including Dermestes maculatus, Trogoderma granarium, and Anthrenus verbasci; Stegobium spp. paniceum), tobacco beetle (Lasioderma serricorne), etc.; horn-breasted flour beetle (Cryptolestes ferrugineus), etc.; saw-breasted flour beetle (Silvanidae), etc.; pollen beetle (Brassicogethes aeneus), etc.;

[0240] Tetranychus spp., Tetranychus kanzawai, Tetranychus urticae, Panonychus citri, Tetranychus evansi, Panonychus ulmi, etc., classified as pests of the order Acari; Aceria diospyri, Shevtchenkella sp., Calacarus carinatus, Acaphylla theavagrans, Aculops lycopersici, Eriophyes chibaensis, Aculops pelekassi, Phyllocoptruta citrus. citri), Aculus schlechtendali, and Aceria tosichella; Tarsonemidae, such as Polyphagotarsonemus latus; Tenuipalpidae, such as Brevipalpus phoenicis; Tuckerellidae; Acaridae, such as Tyrophagus putrescentiae and Tyrophagus similis; and Pyroglyphidae, such as Dermatophagoides farinae and Dermatophagoides pteronyssinus.

[0241] Lepidoptera pests: purple corn borer (Ostrinia scapulalis), Asian corn borer (Ostrinia furnacalis), yellow rice stem borer (Scirpophaga incertulas), rice stem borer (Marasmia exigua), knotty stem borer (Cnaphalocrocis medinalis), bluegrass stem borer (Pediasia teterrellus), striped rice stem borer (Chilo suppressalis), cabbage stem borer (Hellula undalis), grape leaf borer (Herpetogramma luctuosale), cotton leaf borer (Haritalodes derogata), Taiwan rice stem borer (Chilo polychrysus), white water stem borer (Nymphula depunctalis), rice stem borer (Scirpophaga innotata), small sugarcane borer (Diatraea truncatula) saccharalis), eggplant borer (Leucinodes orbonalis), European corn borer (Ostrinia nubilalis), etc.; stem borer (Pyralidae), such as Mediterranean mealybug (Ephestia kuehniella), powdery moth (Cadra cautella), Indian grain moth (Plodia interpunctella), dark-spotted stem borer (Euzophera batangensis), and South American corn seedling borer (Elasmopalpus lignosellus);African armyworm (Spodoptera exempta), secretion armyworm (Mythimna separata), golden armyworm (Plusia festucae), stem borer (Sesamia inferens), sugar beet armyworm (Spodoptera exigua), gray armyworm (Spodoptera mauritia), black-spotted armyworm (Autographa nigrisigna), cutworm (Agrotis ipsilon), fall armyworm (Spodoptera frugiperda), tobacco budworm (Heliothis virescens), cutworm (Spodoptera litura), rice borer (Naranga aenescens), cabbage armyworm (Mamestra brassicae), cutworm (Spodoptera eridania), soybean looper (Chrysodeixis includens), cowworm (Spodoptera cosmioides), and Trichoplusia spp.), corn borer (Helicoverpa zea), cotton bollworm (Helicoverpa armigera), cabbage looper (Trichoplusia ni), cutworm (Agrotis segetum), pale sword moth (Spodoptera depravata), tobacco borer (Helicoverpa assulta), base white moth (Aedia leucomelas), African pink stem borer (Sesamia calamistis), cotton leafworm (Alabama argillacea), hop vine borer moth (Hydraecia immanis), soybean moth (Pseudoplusia includens), velvet bean caterpillar (Anticarsia gemmatalis); European white butterfly (Pieris brassicae), white white butterfly (Pieris rapae) and other butterflies (Pieridae);Tortricidae moths such as Matsumuraeses azukivora, Archips xylosteanus, Tetramoera schistaceana, Cydia pomonella, Grapholita dimorpha, Adoxophyes honmai, Homona magnanima, Grapholita molesta, Leguminivorella, Archips fuscocupreanus, Adoxophyes orana fasciata, Citrus fruit borer (Citripestis sagittiferella), Lobesia botrana, and Epinotia aporema; and Phyllonorycter ringoniella), Caloptilia theivora, and Phyllocnistis citrella; Carposinidae, such as Carposina sasakii; Lyonetiidae, such as Lyonetia prunifoliella, Lyonetia clerkella, and Leucoptera coffeella; Lymantriidae, such as Lymantria dispar and Euproctis pseudoconspersa; Plutellidae, such as Plutella xylostella; Helcystogramma triannulella, Phthorimaea operculella, and Tuta spp. absoluta), peach twig moth (Anarsia lineatella), red bell moth (Pectinophora gossypiella), and other moths (Gelechiidae);Arctiidae, including the American white moth (Hyphantria cunea); Castniidae, including the giant sugarcane borer (Telchin licus); Cossidae, including the aromatic wood borer (Cossus insularis); Geometridae, including the plum ant moth (Cystidia couaggaria) and the large bridge-building moth (Ascotis selenaria); Limacodidae, including the brown-green moth (Parasa consocia), the yellow moth (Monema flavescens), and the beautiful green moth (Parasa lepida); Stathmopodidae, including the persimmon moth (Stathmopoda masinissa); Acherontia hawkmoth (Acherontia spp. lachesis) and other hawkmoths (Sphingidae); honeybee clearwing moths (Nokona feralis), apple clearwing moths (Synanthedon hector), and persimmon clearwing moths (Synanthedon tenuis); straight-striped rice butterfly (Parnara guttata) and other hesperiidae; clothes moths (Tinea translucens) and small clothes moths (Tineola bisselliella); citrus swallowtail butterflies (Papilio Xuthus) and yellow swallowtail butterflies (Papilio machaon hippocrates).

[0242] Nematodes classified as Aphelenchoides besseyi and other Aphelenchoididae; Pratylenchus penetrans, Pratylenchus coffeae, Pratylenchus neglectus, Pratylenchus brachyurus, and Radopholus similis and other Pratylenchidae; Meloidogyne hapla, Meloidogyne incognita, and Meloidogyne javanica; Globodera rostochiensis, Globodera pallida, and Heterodera spp. glycines), guava root-knot nematodes (Meloidogyne enterolobii), etc.; Hoplolaimidae (Hoplolaimidae), etc.; Anguinidae (Anguinidae), etc.; Tylenchulidae (Tylenchus semipenetrans), etc.; Longidoridae (Longidoridae), etc.; Trichodoridae; and Parasitaphelenchidae (Parasitaphelenchidae), etc.

[0243] Agricultural and horticultural insecticides, acaricides, nematicides, or soil pesticides containing the compounds of the present invention are particularly effective in controlling plant parasitic mites, agricultural pests, plant parasitic nematodes, and the like. Among them, since they exhibit excellent effects in controlling plant parasitic mites and agricultural pests, they are very useful as insecticides or acaricides. Furthermore, agricultural and horticultural insecticides, acaricides, nematicides, or soil pesticides containing the compounds of the present invention are also effective in controlling various pests resistant to existing agents such as organophosphorus agents, carbamate agents, synthetic pyrethroid agents, and neonicotinoid agents. Furthermore, since the compounds of the present invention have excellent penetration and migration properties, by applying the agricultural and horticultural insecticides, acaricides, nematicides, or soil pesticides containing the compounds of the present invention to the soil, pests on the stems and leaves can be controlled simultaneously with controlling soil-harming insects, mites, nematodes, gastropods, and isopods.

[0244] Another desirable aspect of the insecticide, acaricide, nematicide or soil pesticide containing the compound of the present invention is an agricultural and horticultural insecticide, acaricide, nematicide or soil pesticide that comprehensively controls the aforementioned agricultural pests, gastropods, plant parasitic mites, plant parasitic nematodes, soil pests, etc.

[0245] The pest control agent containing the compound of the present invention can be used to control fruits and vegetables such as tomatoes, mini tomatoes, green peppers, eggplants, cucumbers, summer squash, watermelons, melons, pumpkins, okra, peppers, winter melons, bitter melons, and cantaloupes; leafy vegetables such as lettuce, leaf lettuce, spinach, cabbage, onions, garlic, asparagus, broccoli, cauliflower, Chinese cabbage, basel, scallions, mizuna, perilla, komatsuna, and celery; root vegetables such as potatoes, sweet potatoes, radishes, carrots, burdock, lotus roots, taro, konjac, yam, ginger, turnips, chives, radishes, and thistles; beans such as soybeans, red beans, peas, kidney beans, peanuts, broad beans, and edamame; cereals such as rice, wheat, oats, rye, and corn; apples, citrus fruits, pears, grapes, strawberries, walnuts, Fruit trees, fruits, and seeds such as almonds, bananas, figs, pineapples, peaches, nectarines, cherries, apricots, coconuts, avocados, persimmons, plums, pistachios, kiwis, and loquats; grasses such as zoysia and bentgrass; flowers such as chrysanthemums, lilies, roses, carnations, dahlias, gerberas, African violets, tulips, daffodils, petunias, lily of the valley, peonies, cyclamen, impatiens, and lisianthus; flowers and trees such as azaleas; craft crops such as cotton, rapeseed, sugar beets, tea, tobacco, coffee, olives, sugarcane, hops, sesame, parsley, thyme, rosemary, basil, and lavender; ornamental foliage plants such as orchids, cacti, and ferns; and pasture grasses such as clover, alfalfa, orchard grass, and stonecrop. These are useful plants for agricultural and horticultural use.

[0246] Furthermore, these plants include plants to which tolerance to herbicides (e.g., HPPD inhibitors such as isoxaflutole; ALS inhibitors such as imazethapyr and thifensulfuron-methyl; EPSP synthase inhibitors such as glyphosate; glutamine synthase inhibitors such as glufosinate; acetyl CoA carboxylase inhibitors such as sethoxydim; bromoxynil; dicamba; 2,4-D) has been imparted through classical breeding methods. Furthermore, these plants also include transformed plants produced through genetic recombination or gene editing techniques. Examples of transgenic plants include transgenic plants tolerant to the aforementioned herbicides, transgenic plants resistant to pests, transgenic plants related to plant components, and transgenic plants resistant to plant pathogens.

[0247] Pest control agents containing the compounds of the present invention are usually mixed with various adjuvants and formulated into various forms such as powders, granules, granular hydrates, hydrates, aqueous suspensions, oily suspensions, granular aqueous solutions, aqueous solutions, emulsions, liquids, pastes, aerosols, and microsprays. However, as long as it is suitable for the purpose of the present invention, it can be in any formulation form commonly used in this field. As auxiliary agents used in the preparation, there can be mentioned solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, baking soda, Glauber's salt, zeolite, starch, etc.; water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-tetrahydropyrrolidone, Solvents such as alcohols; anionic surfactants such as fatty acid salts, benzoates, alkyl sulfosuccinates, dialkyl sulfosuccinates, polycarboxylates, alkyl sulfates, alkyl sulfates, alkyl aryl sulfates, alkyl diglycol ether sulfates, alcohol sulfates, alkyl sulfonates, alkyl aryl sulfonates, aryl sulfonates, lignin sulfonates, alkyl diphenyl ether disulfonates, polystyrene sulfonates, alkyl phosphates, alkyl aryl phosphates, styryl aryl phosphates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl aryl ether sulfates, polyoxyethylene alkyl aryl ether sulfates, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkyl aryl phosphates, and naphthalene sulfonate formaldehyde condensates; such as sorbitol fatty acid esters, glycerol fatty acid esters, fatty acid polyglycerol esters, fatty acid alcohol polyglycol ethers, acetylene glycol, acetylene alcohol, oxyalkylene block polymers, polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, and polyoxyethylene styryl aryl ethers , polyoxyethylene glycol alkyl ether, polyethylene glycol, polyoxyethylene fatty acid ester, polyoxyethylene sorbitol fatty acid ester, polyoxyethylene glycerol fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxypropylene fatty acid ester of nonionic surfactants; olive oil, kapok oil, castor oil, palm oil, camellia oil, palm oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil, liquid paraffin and other vegetable oils or mineral oils; silicone oil, etc. As long as the components of these auxiliary agents do not deviate from the purpose of the present invention, one or more of them can be appropriately selected for use. In addition, in addition to the aforementioned auxiliary agents, it is also possible to appropriately select and use from those known in the art, for example, various commonly used auxiliary agents such as extenders, viscosity enhancers, anti-settling agents, antifreeze agents, dispersion stabilizers, phytotoxicity reducing agents, and mildew inhibitors can also be used. The blending ratio (weight ratio) of the compound of the present invention and various auxiliary agents is 0.001:99.999~95:5, preferably 0.005:99.995~90:10.When these preparations are actually used, they can be used directly or diluted with a diluent such as water to a specified concentration. If necessary, various spreaders (surfactants, vegetable oils, mineral oils, etc.) can be added.

[0248] The application of pest control agents containing the compounds of the present invention cannot be determined uniformly due to variations in weather conditions, formulation form, application time, application location, type of pest, or occurrence, but generally, the active ingredient concentration is 0.1 to 50,000 ppm, preferably 1 to 30,000 ppm, and the application rate per unit area is 0.01 to 50,000 g, preferably 1 to 30,000 g, of the compound of the present invention per hectare. The present invention also includes methods for controlling pests, mites, nematodes, or soil pests, particularly plant parasitic mites, agricultural pests, and plant parasitic nematodes, using such application methods.

[0249] Application of various pest control formulations containing the compounds of the present invention, or dilutions thereof, is generally carried out by commonly used application methods, such as spreading (e.g., spraying, atomizing, granulation, surface application, etc.), soil application (mixing, pouring, etc.), surface application (coating, dusting, covering, etc.), and impregnation with poison bait. Furthermore, the active ingredient can be mixed with feed and administered to livestock to inhibit the occurrence and reproduction of pests, particularly harmful insects, in their excrement. Furthermore, application can be carried out by the so-called ultra-low volume application method. In this method, the active ingredient can be contained at 100%. For example, when a pest control agent containing a compound of the present invention is applied to plants, an effective amount of the pest control agent can be applied directly and / or to the soil or plant body to control pests such as insects, mites, nematodes, and soil pests. The aforementioned plant system refers to the aboveground parts (e.g., stems, leaves, trunks), underground parts (e.g., roots), or seeds of the plant to which the pest control agent is applied. The aforementioned seeds refer to the dispersal bodies (i.e., so-called seeds) formed by sexual reproduction, plant organs (e.g., tubers, bulbs, corms, rhizomes, seed tubers), or cuttings of fruit trees, flowers, or flowers (e.g., grape branches of fruit trees).

[0251] In this case, the application of the pest control agent containing the compound of the present invention to plants can be carried out, for example, by soil treatment, stem and leaf treatment, irrigation treatment, seed treatment, trunk injection treatment, or rice seedling box application. Generally speaking, for soil treatment, stem and leaf treatment, or irrigation treatment, the application amount can be set at 0.01g to 50,000g of the compound of the present invention per hectare, preferably 1g to 30,000g. For seed treatment, the application amount can be set at 0.01g to 200g per kg of seeds, preferably 0.05g to 100g. For rice seedling box application, the application amount can be set at 0.001g to 3,000g of the compound of the present invention per seedling box, preferably 0.01g to 1,000g. In the case of injection treatment into tree trunks, the appropriate amount of the compound of the present invention may be applied in an amount of 0.001 g to 5,000 g, preferably about 0.01 g to 3,000 g, per tree.

[0252] In the above, the so-called soil treatment includes, for example, a method in which the compound of the present invention is prepared into a liquid preparation (liquid, aqueous suspension, oily suspension, emulsion, etc.) or a solid preparation (granules, powder, hydrate, aqueous solvent, granular hydrate, granular aqueous solvent, etc.), directly or diluted with water, and then spread on the soil for mixing before transplanting or sowing plants; a method in which the compound is spread in a drilled hole (planting hole) for planting plants; or a method in which the compound is spread in a shallow trench of a certain width dug for planting seeds or plants.

[0253] For example, the so-called stem and leaf treatment includes preparing the compound of the present invention into a liquid preparation (liquid, aqueous suspension, oily suspension, emulsion, etc.) or a solid preparation (hydrate, aqueous solvent, granular hydrate, granular aqueous solvent, etc.), diluting it with water, and spreading it over the entire plant body.

[0254] The so-called perfusion treatment includes, for example, a method in which the compound of the present invention is prepared into a liquid preparation (liquid, aqueous suspension, oily suspension, etc.) or a solid preparation (hydrate, aqueous solution, granular hydrate, granular aqueous solution, etc.), and then directly or diluted with water and perfused into a cultivation container for seedlings, the plant head of a plant under cultivation, or the vicinity thereof.

[0255] Seed treatment includes, for example, a method in which the compound of the present invention is prepared into a liquid preparation (aqueous suspension, oily suspension, emulsion, liquid, etc.) or a solid preparation (powder, hydrate, aqueous solution, granular hydrate, granular aqueous solution, etc.), and the mixture is directly or diluted with water, and stirred with the seeds to adhere to the seed surface; a method in which the mixture is mixed with a coating material and adhered to the seed surface; a method in which the mixture is blown onto the seeds to adhere to the seeds; a method in which the seeds are immersed in the agent to allow the agent to penetrate the seeds, etc.

[0256] Application to rice seedling boxes includes, for example, preparing the compound of the present invention into a solid preparation (granules, powders, etc.) or a liquid preparation (aqueous suspension, oily suspension, liquid, etc.), directly or diluted with water, and spreading it in the seedling box before sowing, after sowing, before or after sowing, during the growth period in the seedling box, or before transplanting in paddy fields. Furthermore, in the seedling box, mixing with the soil at the time of sowing can be performed, for example, preparing the compound of the present invention into a solid preparation (granules, powders, granular hydrates, etc.) and mixing it into the bed soil, covering soil, or the entire soil.

[0257] The so-called trunk injection treatment includes, for example, a method in which the compound of the present invention is prepared into a liquid preparation (liquid preparation, etc.) and injected directly into the plant body through a hole drilled in the trunk.

[0258] Furthermore, agricultural and horticultural insecticides, acaricides, nematicides, or soil insecticides containing the compounds of the present invention can be mixed or used in combination with other pesticides, fertilizers, pesticide damage reduction agents, etc. In this case, even better effects and properties may be exhibited. The aforementioned mixing or use means that the compound of the present invention and the other component are used simultaneously, separately, or at intervals. Examples of other pesticides include herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antivirals, attractants, antibiotics, plant hormones, and plant growth regulators. In particular, mixing or using the compound of the present invention with one or more active ingredient compounds of other pesticides in an insecticidal composition, acaricide composition, nematicidal composition, or soil insecticide composition can improve the scope of application, the period of treatment, and the control activity. In addition, the compound of the present invention and the other active ingredient compound of the pesticide can be formulated separately and mixed for use during spraying, or they can be formulated together for use. The present invention also includes such insecticidal compositions, acaricidal compositions, nematicidal compositions, or soil pesticidal compositions.

[0259] The mixing ratio of the compound of the present invention and the active ingredient compound of other insecticides and / or nematicides (compound of the present invention: other active ingredient compound) cannot be determined uniformly due to differences in meteorological conditions, formulation form, target crop, application period, application location, pest or nematode type or occurrence, etc., but the weight ratio can generally be set at 1:300 to 300:1, preferably 1:100 to 100:1. Furthermore, the appropriate application amount is 0.1 to 70,000 g of the total active ingredient compound per hectare, preferably 5 to 50,000 g. The present invention also includes a method for controlling pests and nematodes by applying such a mixed insecticide and nematicide composition.

[0260] Among the other pesticides, the insecticide, acaricide, nematicide, or soil insecticide, i.e., the active ingredient compound (common name or Japan Plant Protection Association test code) of the insecticide can be appropriately selected from the following compound groups. Even if there is no special description, the presence of various structural isomers such as salts, alkyl esters, and optical isomers in these compounds is of course also included. For example, profenofos, dichlorvos, fenamiphos, fenitrothion, EPN ((RS)-(O-ethyl O-4-nitrophenyl)-1,2-dichloroisothiazolinone, ...phenylphosphonothioate), diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiofos, fosthiazate, cadusafos, disulfoton, isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate, sulprofos, thiometon, vamidothion, pyraclofos, pyridaphenthion, pirimiphos-methyl, propaphos, phosalone, and fumu pine ( organophosphate compounds including chlorfenvinphos, chlorfenvinphos, trichlorfon, methidathion, phenthoate, oxydeprofos (ESP), azinphos-methyl, fenthion, heptenophos, parathion, phosphocarb, demeton-S-methyl, monocrotophos, methamidophos, imicyafos, parathion-methyl, terbufos, phosphamidon, phosmet, and phorate;Such as carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, carbosulfan, benfuracarb, bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb, XMC (3,5-xylyl methylcarbamate), and fenothiocarb carbamate compounds; such as cartap, thiocyclam, thiocyclam oxalate, thiocyclam hydrochloride, neristoxin derivatives such as thiosulfate hydrochloride, bensultap, thiosultap, monosultap (also known as thiosultap-monosodium), bisultap (also known as thiosultap-disodium), and polythialan; organochlorine compounds such as dicofol, tetradifon, endosulfan, dienochlor, dieldrin, and methoxychlor; organotin compounds such as fenbutatin oxide, cyhexatin, and azocyclotin;Such as fenvalerate, permethrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, theta-cypermethrin, beta-cypermethrin, deltamethrin, cyhalothrin, gamma-cyhalothrin, lambda - lambda-cyhalothrin, tefluthrin, kappa-tefluthrin, etofenprox, flufenprox, cyfluthrin, beta-cyfluthrin, fenpropathrin, flucythrinate, fluvalinate, cycloprothrin rin), pyrethrins, esfenvalerate, tetramethrin, resmethrin, protrifenbute, bifenthrin, kappa-bifenthrin, acrinathrin, allethrin, tau-fluvalinate, tralomethrin, profluthrin Pyrethroid compounds including luthrin, metofluthrin, epsilon-metofluthrin, heptafluthrin, phenothrin, flumethrin, momfluorothrin, epsilon-momfluorothrin, silafluofen, and chloroprallethrin;Benzyl urea compounds such as diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron, novaluron, triflumuron, hexaflumuron, bistrifluron, noviflumuron, fluazuron, and flufenoxuron; Juvenile hormone compounds such as methoprene, pyriproxyfen, fenoxycarb, and diofenolan; Pyridazinone compounds such as pyridaben; Pyrazole compounds such as fenpyroximate, cyenopyrafen, and cyetpyrafen; Phenylpyrazole compounds such as acetoprole, ethiprole, fipronil, flufiprole, pyrafluprole, pyriprole, nicofluprole, and vaniliprole; carboxamide compounds such as pyflubumide, tebufenpyrad, tolfenpyrad, and dimpropyridaz; Pyridylpyrazole compounds such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetrachlorantraniliprole, tetranimid, tyclopyrazoflor, fluchlordiniliprole, and tiorantraniliprole; neonicotinoid compounds such as imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, dinotefuran, and nithiazine;Hydrazine compounds such as tebufenozide, methoxyfenozide, chromafenozide, and halofenozide; Pyridine compounds such as pyridalyl and flonicamid; Tetronic acid compounds such as spirodiclofen, spiromesifen, and spirobudifen; Quaternary ammonium acid compounds such as spirotetramat, spiropidion, and spidoxamat; Strobilurin compounds such as fluacrypyrim, pyriminostrobin, and flupyroxystrobin; Pyrimidinamine compounds such as flufenerim and pyrimidifen; Organosulfur compounds such as malathion; Triamide compounds such as cyromazine; Hydrazone compounds such as hydramethylnon; Phthalicylamide compounds such as flubendiamide and cyhalodiamide; Diamide compounds such as broflanilide, cyproflanilide, and modoflaner; Thiourea compounds such as diafenthiuron and chloromethiuron; Formamidine compounds such as amitraz, chlordimeform, and chloromebuform; Azomethine compounds such as pymetrozine and pyrifluquinazon; Isoxazoline compounds such as afoxolaner, fluralaner, fluxametamide, sarolaner, isocycloseram, umifoxolaner, tigolaner, and mivorilaner; fluoroolefin compounds such as fluensulfone and trifluenfuronate;Mesoionic compounds such as dicloromezotiaz, triflumezopyrim, and fenmezoditiaz; Pyropene compounds such as afidopyropen; Other compounds include buprofezin, hexythiazox, triazamate, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, 1,3-dichloropropene, benclothiaz, bifenazate, propargite, clofentezine, metaflumizone, cyflumetofen, fenazaquin, amidoflumet, and sulfluram. compounds such as chlorpyrifos, chloranil, dapoxetine ...

[0261] In addition, it can also be combined with the following compounds. For example, crystalline protein toxins of Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis, Bacillus thuringiensis, Paecilomyces lilacinus, Bacillus methylotrophicus, Bacillus subtilis, Bacillus amyloliquefaciens, or Bacillus licheniformis, insect pathogenic viral agents, insect pathogenic filamentous fungi, nematode pathogenic filamentous fungi, etc.; microbial pesticides such as abamectin, emamectin benzoate, ivermectin, milbemectin, milbemycin Antibiotics and semi-synthetic antibiotics such as oxime, lepimectin, spinosad, and spinetoram; natural products such as azadirachtin, rotenone, and ryanodine; repellents such as deet; physical pest control agents such as paraffin oil and mineral oil; and RNAi pesticides such as ledprona.

[0262] The active ingredient compound (common name or Japan Plant Protection Association test code) of the fungicide in the other pesticides mentioned above can be appropriately selected from the following compound groups. Even if not specifically stated, when these compounds exist as salts, alkyl esters, optical isomers, and various structural isomers, these are of course also included. Anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, and cyprodinil; Triazolopyrimidine compounds such as ametoctradin; Triazolobenzothiazole compounds such as tricyclazole; Pyridineamine compounds such as fluazinam; Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, furconazole- cis), prochloraz, metconazole, epoxiconazole, tetraconazole, oxpoconazole fumarate, prothioconazole, triadimenol, flutriafol, difenoconazole, fluquinconazole, fenbuconazole, bromuconazole, diniconazole, simeconazole, pefurazoate, ipconazole, imibenconazole, azaconazole, triticonazole, imazalil, ipfentrifluconazole, mefentrifluconazole, and fluoxytioconazole;Quinoline compounds such as chinomethionat; dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, and thiram; organochlorine compounds such as phthalide, chlorothalonil, and quintozene; benzimidazole compounds such as benomyl, thiophanate-methyl, carbendazim, thiabendazole, and fuberidazole; cyanoacetamide compounds such as cymoxanil; Phenylamide compounds such as metalaxyl, metalaxyl-M (also known as mefenoxam), oxadixyl, ofurace, benalaxyl, benalaxyl-M (also known as kiralaxyl, chiralaxyl), furalaxyl, and valifenalate; aniline compounds such as cyprofuram, carboxin, oxycarboxin, thifluzamide, boscalid, fenhexamid, isotianil, tiadinil, and pyraziflumid; Sulfonamide (sulfenic acid) compounds such as dichlofluanid and tolylfluanid; Copper compounds such as cupric hydroxide, organic copper (oxine copper), anhydrous copper sulfate, copper nonylphenolsulfonate, 8-hydroxyquinoline copper, and dodecylbenzenesulfonic acid bis(ethylenediamine)copper complex (II) (also known as DBEDC); Organophosphorus compounds such as fosetyl-Al, tolclofos-Methyl, edifenphos, and iprobenfos; Phthalimide compounds such as captan, captafol, and folpet;Dicarboximide compounds such as procymidone, iprodione, and vinclozolin; benzanilide compounds such as flutolanil, mepronil, benodanil, and flufenoxadiazam; and amide compounds such as carpropamid, diclocymet, silthiofam, and fenoxanil. Carboxamide compounds such as benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, pydiflumetofen, sedaxane, isoflurane, inpyrfluxam, pyrapropoyne, and flubeneteram; and benzamide compounds such as fluopicolide, fluopyram, zoxamide, and fluopimomide; Furanilide compounds such as fenfuram; Thiophenamide compounds such as isofetamido; Piperazine compounds such as triforine; Pyridine compounds such as pyrifenox, pyrisoxazole, and aminopyrifen; Pyrimidine compounds such as fenarimol, ferimzone, nuarimol, and flumetylsulforim; Piperidine compounds such as fenpropidin; Morpholine compounds such as fenpropimorph and tridemorph; Organotin compounds such as fentin hydroxide and fentin acetate; Urea compounds such as pencycuron;Carboxylic acid amide compounds such as dimethomorph, flumorph, pyrimorph, iprovalicarb, benthiavalicarb-isopropyl, and mandipropamid; phenylcarbamate compounds such as diethofencarb; cyanopyrrole compounds such as fludioxonil and fenpiclonil; Such as azoxystrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, picoxystrobin, orysastrobin, dimoxystrobin, pyraclostrobin, fluoxastrobin, pyraoxystrobin, pyrametostrobin, coumoxystrobin, enoxastrobin, fenaminstrobin, flufenoxystrobin, triclopyricarb, and strobilurin compounds of the mandestrobin family; such as oxazole compounds of the famoxadone, oxathiapiprolin, and fluoxapiprolin family; Carboxamide compounds such as ethaboxam; imidazolinone compounds such as fenamidone; benzenesulfonamide compounds such as flusulfamide; oxime ether compounds such as cyflufenamid; anthraquinone compounds such as dithianon; crotonic acid compounds such as meptyldinocap; antibiotics such as validamycin, kasugamycin, streptomycin, and polyoxins; guanidine compounds such as iminoctadine, dodine, and guazatine;Aliphatic nitrogen compounds such as butylamine and seboctylamine; Quinoline compounds such as tebufloquin, quinoxyfen, quinofumelin, and ipflufenoquin; Thiazolidine compounds such as flutianil; Carbamate compounds such as propamocarb hydrochloride, pyribencarb, and tolprocarb; Tetrazole compounds such as picarbutrazox and metyltetraprole; Sulfonamide compounds such as amisulbrom and cyazofamid; Allylphenyl ketone compounds such as metrafenone and pyriofenone; Benzothiazole compounds such as probenazole and dichlobentiazox; Phenylpyrazole compounds such as fenpyrazamine; Dithiolane compounds such as isoprothiolane; Pyridinamide compounds such as fenpicoxamid, florylpicoxamid, and metarylpicoxamid; Pyridachlometyl compounds such as pyridachlometyl; Sulfur compounds such as sulfur and lime sulfur; Hydrazide compounds such as chloroinconazide; Other compounds include pyroquilon, diclomezine, chloropicrin, dazomet, metam-sodium, proquinazid, spiroxamine, and dipymetitrone;Microbial fungicides such as Bacillus amyloliqefaciens strain QST713, Bacillus amyloliqefaciens strain FZB24, Bacillus amyloliqefaciens strain MBI600, Bacillus amyloliqefaciens strain D747, Pseudomonas fluorescens, Bacillus subtilis, and Trichoderma atroviride SKT-1; and plant extracts such as tea tree oil.

[0263] Next, several desirable embodiments of the present invention are exemplified, but these are not intended to limit the present invention. (1) A pyridazinone compound represented by the aforementioned formula (I) or a salt thereof. (2) The pyridazinone compound or a salt thereof as described in (1), wherein Y and RA are independently halogen, (C 1-C 4) alkyl, (C 2-C 4) alkenyl, (C 2-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) haloalkoxy, (C 1-C 4) alkylthio, (C 1-C 4) alkylsulfinyl, (C 1-C 4) alkylsulfonyl, (C 1-C 4) haloalkylthio, (C 1-C 4) haloalkylsulfinyl, (C 1-C 4) haloalkylsulfonyl, hydroxy, cyano, nitro, -SF 5, -NR BR C, -C(═O)RD or -C(═O)NR ER F; Z is (C 1-C 5) alkyl, (C 2-C 4) alkenyl, (C 2-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) alkyl, (C 3-C 6) cycloalkyl, (C 1-C 4) alkyl or (C 1-C 4) haloalkyl; R 1, R 2, R 3 and R 4 are halogen, (C 1-C 4) alkyl, (C 2-C 4) alkenyl, (C 2-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 3-C 6) cycloalkyloxy, (C 1-C 4) haloalkoxy, (C 1-C 4) alkylthio, (C 1-C 4)alkylsulfinyl, (C 1-C 4)alkylsulfonyl, (C 1-C 4)haloalkylthio, (C 1-C 4)haloalkylsulfinyl, (C 1-C 4)haloalkylsulfonyl, hydroxy, cyano, nitro, -NR GR H, -C(=O)RI, -C(=O)NR JR k, -C(=NOR L)RM, dimethoxymethyl, 1,3-dioxan-2-yl, or 1,3-dioxolan-2-yl; RB, RC, RE, RF, RG, RH, RJ, and RK are each a hydrogen atom, a (C 1-C 4)alkyl group, or a (C 1-C 4)haloalkyl group; RD and RI are each a hydrogen atom, a hydroxyl group, a (C 1-C 4)alkyl group, a (C 1-C 4)haloalkyl group, or a (C 1-C 4)alkoxy group; RL and RM are each a hydrogen atom or a (C 1 -C 4 ) alkyl group.(3) A pyridazinone compound or a salt thereof as described in (1), wherein Y and RA are independently halogen, (C 1-C 4) alkyl, (C 2-C 4) alkenyl, (C 2-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) haloalkoxy, (C 1-C 4) alkylsulfonyl, (C 1-C 4) haloalkylthio, (C 1-C 4) haloalkylsulfinyl, (C 1-C 4) haloalkylsulfonyl, cyano, nitro or -C(=O)RD; and Z is (C 1-C 5) alkyl, (C 3-C 6) cycloalkyl, (C 1-C 4) alkoxy (C 1-C 4) alkyl or (C 1-C R1, R2, R3 and R4 are independently halogen, (C1-C4)alkyl, (C2-C4)alkynyl, (C3-C6)cycloalkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfinyl, (C1-C4)alkylsulfonyl, cyano, nitro, -NRGRH, -C(=O)RI, -C(=NOR L)RM, dimethoxymethyl, 1,3-dioxan-2-yl or 1,3-dioxolan-2-yl; RG and RH are independently a hydrogen atom or (C1-C4)alkyl; RD and RI are independently a hydrogen atom, (C1-C4)alkyl or (C1-C4)alkyl RL and RM are independently a hydrogen atom or a (C 1-C 4) alkyl group.(4) A pyridazinone compound or a salt thereof as described in (1), wherein Y and RA are independently halogen, (C 1-C 4) alkyl, (C 2-C 4) alkenyl, (C 2-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) haloalkoxy, (C 1-C 4) alkylsulfonyl, cyano, nitro or -C(=O)RD; Z is (C 1-C 4) alkyl, (C 3-C 6) cycloalkyl, (C 1-C 4) alkoxy (C 1-C 4) alkyl or (C 1-C 4) haloalkyl; R 1, R 2, R 3 and R 4 are independently halogen, (C 1-C 4) alkyl, (C 2-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) alkylsulfonyl, cyano, nitro or -C(=O)RD; 4)alkyl, (C 1-C 4)alkylsulfinyl, (C 1-C 4)alkylsulfonyl, (C 1-C 4)haloalkylthio, (C 1-C 4)haloalkylsulfinyl, (C 1-C 4)haloalkylsulfonyl, cyano, nitro, -C(=O)RI, -C(=NOR L)RM, dimethoxymethyl, 1,3-dioxan-2-yl or 1,3-dioxolan-2-yl; RD is a (C 1-C 4)alkyl group; RI is a hydrogen atom; RL and RM are each a hydrogen atom or a (C 1-C 4)alkyl group. (5) A pyridazinone compound or a salt thereof as described in (1), wherein Y and RA are independently halogen, (C 1-C 4) alkyl, (C 1-C 4) alkenyl, (C 1-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) haloalkoxy, (C 1-C 4) alkylsulfonyl, (C 1-C 4) haloalkylthio, (C 1-C 4) haloalkylsulfinyl, (C 1-C 4) haloalkylsulfonyl, cyano or nitro; Z is (C 1-C 4) alkyl, (C 3-C 6) cycloalkyl, (C 1-C 4) alkoxy (C 1-C 4) alkyl or (C 1-C 4) haloalkyl; R 1, R R2, R3 and R4 are each represented by halogen, (C1-C4)alkyl, (C3-C6)cycloalkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfinyl or nitro.(6) A pyridazinone compound or a salt thereof as described in (1), wherein Y and RA are independently halogen, (C 1-C 4) alkyl, (C 1-C 4) alkenyl, (C 1-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) haloalkoxy, (C 1-C 4) alkylsulfonyl, (C 1-C 4) haloalkylthio, (C 1-C 4) haloalkylsulfinyl, (C 1-C 4) haloalkylsulfonyl, cyano or nitro; Z is (C 1-C 4) alkyl, (C 3-C 6) cycloalkyl, (C 1-C 4) alkoxy (C 1-C 4) alkyl or (C 1-C 4) haloalkyl; R 1, R 2. R 3 and R 4 are each represented by halogen, (C 1-C 4) alkyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) haloalkoxy or nitro. (7) The pyridazinone compound or salt thereof as described in (1) or (2), wherein Y is bonded to the para position relative to the pyridazinone ring, and Y is halogen, (C 1-C 4) alkyl, (C 2-C 4) alkenyl, (C 2-C 4) alkynyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) haloalkoxy, (C 1-C 4) alkylthio, (C 1-C 4) alkylsulfinyl, (C 1-C 4) alkylsulfonyl, (C 1-C 4) haloalkylthio, (C 1-C 4) haloalkylsulfinyl, (C 1-C 4) haloalkylsulfonyl, cyano, nitro, -SF 5 or -C(=O)RD. (8) A pyridazinone compound or a salt thereof as described in (1) or (2), wherein Y is bonded to the para position relative to the pyridazinone ring, and Y is a halogen, (C 2 -C 4) alkynyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, (C 1 -C 4) alkylsulfinyl, (C 1 -C 4) alkylsulfonyl, (C 1 -C 4) haloalkylthio, (C 1 -C 4) haloalkylsulfinyl, (C 1 -C 4) haloalkylsulfonyl or cyano. (9) A pyridazinone compound or a salt thereof as described in (1) to (8), wherein Q is represented by Q 1 or Q 3. (10) A pyridazinone compound or a salt thereof as described in any one of (1) to (9), wherein X is represented by CH or C(RA). (11) The pyridazinone compound or a salt thereof according to any one of (1) to (9), wherein X is represented by C(RA).(12) A pyridazinone compound or a salt thereof as described in (11), wherein RA is halogen, (C 1-C 4) alkyl, (C 2-C 4) alkenyl, (C 2-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) haloalkoxy, cyano, nitro or -C(=O)RD. (13) A pyridazinone compound or a salt thereof as described in (11), wherein RA is halogen, (C 1-C 4) alkyl, (C 2-C 4) alkenyl, (C 2-C 4) alkynyl, (C 1-C 4) haloalkyl or (C 1-C 4) alkoxy. (14) A pyridazinone compound or a salt thereof as described in any one of (1) to (9), wherein X is N. (15) A pyridazinone compound or a salt thereof as described in any one of (1) to (9), wherein X is represented by CH. (16) A pyridazinone compound or a salt thereof as described in any one of (1) to (9), wherein X is C(RA) or N, n is 1 or 2, and at least one Y is substituted in the para position relative to the pyridazinone ring. (17) A pyridazinone compound or a salt thereof as described in any one of (1) to (4) and (7) to (16), wherein R1, R2, R3 and R4 are each halogen, (C1-C4)alkyl, (C3-C6)cycloalkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfinyl, (C1-C4)alkylsulfonyl, cyano, nitro, -C(=O)RI or dimethoxymethyl. (18) A pyridazinone compound or a salt thereof as described in any one of (1) to (4) and (7) to (16), wherein R1, R2, R3 and R4 are each halogen, (C1-C4)alkyl, (C3-C6)cycloalkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, nitro or dimethoxymethyl. (19) A pyridazinone compound or a salt thereof as described in any one of (1), (2) and (7) to (18), wherein Z is (C1-C5)alkyl, (C3-C4)cycloalkyl, (C1-C4)alkoxy, (C1-C4)alkyl or (C1-C4)haloalkyl. (20) The pyridazinone compound or salt thereof as described in any one of (1) to (19), wherein n is 1 or 2. (21) The pyridazinone compound or salt thereof as described in any one of (1) to (19), wherein n is 2. (22) The pyridazinone compound or salt thereof as described in any one of (1) to (21), wherein a, b, c and d are 1 or 2, respectively.

[0264] (23) A pyridazinone compound or a salt thereof represented by the aforementioned formula (i). (24) A pyridazinone compound or a salt thereof as described in (23), which is represented by the aforementioned formula (ia), formula (ic), formula (id) or formula (ig). (25) A pyridazinone compound or a salt thereof as described in (23), which is represented by the aforementioned formula (ic), formula (id) or formula (ig). (26) A pyridazinone compound or a salt thereof as described in (23), wherein a is 1 or 2. (27) A pyridazinone compound or a salt thereof represented by the aforementioned formula (ii). (28) A pyridazinone compound or a salt thereof as described in (27), which is represented by the aforementioned formula (ii-b) or formula (ii-c). (29) A pyridazinone compound or a salt thereof as described in (27), wherein b is 1 or 2. (30) A pyridazinone compound or a salt thereof represented by the aforementioned formula (iii). (31) The pyridazinone compound or its salt as described in (30), which is represented by the aforementioned formula (iii-a) or formula (iii-c). (32) The pyridazinone compound or its salt as described in (30), which is represented by the aforementioned formula (iii-c). (33) The pyridazinone compound or its salt as described in (30), wherein c is 1 or 2. (34) The pyridazinone compound or its salt as described in (iv). (35) The pyridazinone compound or its salt as described in (34), which is represented by the aforementioned formula (iv-a) or formula (iv-c). (36) The pyridazinone compound or its salt as described in (34), which is represented by the aforementioned formula (iv-c). (37) The pyridazinone compound or its salt as described in (34), wherein d is 1 or 2.(38) A pyridazinone compound or a salt thereof as described in (23) to (37), wherein Y and RA are each halogen, (C 1-C 4) alkyl, (C 2-C 4) alkenyl, (C 2-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) haloalkoxy, (C 1-C 4) alkylthio, (C 1-C 4) alkylsulfinyl, (C 1-C 4) alkylsulfonyl, (C 1-C 4) haloalkylthio, (C 1-C 4) haloalkylsulfinyl, (C 1-C 4) haloalkylsulfonyl, hydroxyl, cyano, nitro, -SF 5, -NR BR C, -C(=O)RD or -C(=O)NR ER F; Z is (C 1-C 5) alkyl, (C 2-C 4) alkenyl, (C 2-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) alkyl, (C 3-C 6) cycloalkyl, (C 1-C 4) alkyl or (C 1-C 4) haloalkyl; R 1, R 2, R 3 and R 4 are halogen, (C 1-C 4) alkyl, (C 2-C 4) alkenyl, (C 2-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 3-C 6) cycloalkyloxy, (C 1-C 4) haloalkoxy, (C in the group consisting of: -NRGRH, -C(=O)RI, -C(=O)NRJRk, -C(=NOR L)RM, dimethoxymethyl, 1,3-dioxan-2-yl, and 1,3-dioxolan-2-yl; RB, RC, RE, RF, RG, RH, RJ, and RK are each a hydrogen atom, a (C1-C4)alkyl group, or a (C1-C4)haloalkyl group; RD and RI are each a hydrogen atom, a hydroxyl group, a (C1-C4)alkyl group, a (C1-C4)haloalkyl group, or a (C1-C4)haloalkyl group; RL and RM are independently a hydrogen atom or a (C 1-C 4) alkyl group.(39) A pyridazinone compound or a salt thereof as described in (23) to (37), wherein Y and RA are each halogen, (C 1-C 4) alkyl, (C 2-C 4) alkenyl, (C 2-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) haloalkoxy, (C 1-C 4) alkylsulfonyl, (C 1-C 4) haloalkylthio, (C 1-C 4) haloalkylsulfinyl, (C 1-C 4) haloalkylsulfonyl, cyano, nitro or -C(=O)RD; and Z is (C 1-C 5) alkyl, (C 3-C 6) cycloalkyl, (C 1-C 4) alkoxy (C 1-C 4) alkyl or (C R1, R2, R3 and R4 are independently halogen, (C1-C4)alkyl, (C2-C4)alkynyl, (C3-C6)cycloalkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfinyl, (C1-C4)alkylsulfonyl, cyano, nitro, -NRGRH, -C(=O)RI, -C(=NOR L)RM, dimethoxymethyl, 1,3-dioxan-2-yl or 1,3-dioxolan-2-yl; RG and RH are independently a hydrogen atom or (C1-C4)alkyl; RD and RI are independently a hydrogen atom, (C1-C 4) alkyl or (C 1-C 4) alkoxy; RL and RM are independently a hydrogen atom or a (C 1-C 4) alkyl.(40) A pyridazinone compound or a salt thereof as described in (23) to (37), wherein Y and RA are each halogen, (C 1-C 4) alkyl, (C 2-C 4) alkenyl, (C 2-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) haloalkoxy, (C 1-C 4) alkylsulfonyl, cyano, nitro or -C(=O)RD; Z is (C 1-C 4) alkyl, (C 3-C 6) cycloalkyl, (C 1-C 4) alkoxy (C 1-C 4) alkyl or (C 1-C 4) haloalkyl; R 1, R 2, R 3 and R 4 are each halogen, (C 1-C 4) alkyl, (C 2-C 4)alkynyl, (C 3 -C 6)cycloalkyl, (C 1 -C 4)haloalkyl, (C 1 -C 4)alkoxy, (C 1 -C 4)haloalkoxy, (C 1 -C 4)alkylthio, (C 1 -C 4)alkylsulfinyl, (C 1 -C 4)alkylsulfonyl, (C 1 -C 4)haloalkylthio, (C 1 -C 4)haloalkylsulfinyl, (C 1 -C 4)haloalkylsulfonyl, cyano, nitro, -C(=O)RI, -C(=NOR L)RM, dimethoxymethyl, 1,3-dioxan-2-yl or 1,3-dioxolan-2-yl; RD is a (C 1 -C 4)alkyl group; RI is a hydrogen atom; RL and RM are each a hydrogen atom or a (C 1 -C 4)alkyl group. (41) A pyridazinone compound or a salt thereof as described in (23) to (37), wherein Y and RA are each halogen, (C 1-C 4) alkyl, (C 1-C 4) alkenyl, (C 1-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) haloalkoxy, (C 1-C 4) alkylsulfonyl, (C 1-C 4) haloalkylthio, (C 1-C 4) haloalkylsulfinyl, (C 1-C 4) haloalkylsulfonyl, cyano or nitro; and Z is (C 1-C 4) alkyl, (C 3-C 6) cycloalkyl, (C 1-C 4) alkoxy (C 1-C 4) alkyl or (C 1-C 4) haloalkyl; R 1, R 2, R 3 and R 4 are each represented by halogen, (C 1-C 4) alkyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) haloalkoxy, (C 1-C 4) alkylthio, (C 1-C 4) alkylsulfinyl or nitro.(42) A pyridazinone compound or a salt thereof as described in (23) to (37), wherein Y and RA are each halogen, (C 1-C 4) alkyl, (C 1-C 4) alkenyl, (C 1-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) haloalkoxy, (C 1-C 4) alkylsulfonyl, (C 1-C 4) haloalkylthio, (C 1-C 4) haloalkylsulfinyl, (C 1-C 4) haloalkylsulfonyl, cyano or nitro; and Z is (C 1-C 4) alkyl, (C 3-C 6) cycloalkyl, (C 1-C 4) alkoxy (C 1-C 4) alkyl or (C 1-C 4) haloalkyl; R 1, R 2, R 3 and R 4 are each represented by halogen, (C 1-C 4)alkyl, (C 3-C 6)cycloalkyl, (C 1-C 4)haloalkyl, (C 1-C 4)alkoxy, (C 1-C 4)haloalkoxy or nitro. (43) A pyridazinone compound or a salt thereof as described in any one of (23) to (38), wherein Y is bonded to the para position relative to the pyridazinone ring, and Y is a halogen, (C1-C4) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, (C1-C4) haloalkyl, (C1-C4) alkoxy, (C1-C4) haloalkoxy, (C1-C4) alkylthio, (C1-C4) alkylsulfinyl, (C1-C4) alkylsulfonyl, (C1-C4) haloalkylthio, (C1-C4) haloalkylsulfinyl, (C1-C4) haloalkylsulfonyl, cyano, nitro, -SF5 or -C(=O)RD. (44) A pyridazinone compound or a salt thereof as described in any one of (23) to (38), wherein Y is bonded to the para position relative to the pyridazinone ring, and Y is a halogen, (C 2 -C 4) alkynyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, (C 1 -C 4) alkylsulfinyl, (C 1 -C 4) alkylsulfonyl, (C 1 -C 4) haloalkylthio, (C 1 -C 4) haloalkylsulfinyl, (C 1 -C 4) haloalkylsulfonyl, or cyano. (45) A pyridazinone compound or a salt thereof as described in any one of (23) to (44), wherein X is represented by CH or C(RA). (46) A pyridazinone compound or a salt thereof as described in any one of (23) to (44), wherein X is represented by C(RA).(47) A pyridazinone compound or a salt thereof as described in (46), wherein RA is halogen, (C 1-C 4) alkyl, (C 2-C 4) alkenyl, (C 2-C 4) alkynyl, (C 3-C 6) cycloalkyl, (C 1-C 4) haloalkyl, (C 1-C 4) alkoxy, (C 1-C 4) haloalkoxy, cyano, nitro or -C(=O)RD. (48) A pyridazinone compound or a salt thereof as described in (46), wherein RA is halogen, (C 1-C 4) alkyl, (C 2-C 4) alkenyl, (C 2-C 4) alkynyl, (C 1-C 4) haloalkyl or (C 1-C 4) alkoxy. (49) The pyridazinone compound or salt thereof as described in any one of (23) to (44), wherein X is represented by N. (50) The pyridazinone compound or salt thereof as described in any one of (23) to (44), wherein X is represented by CH. (51) The pyridazinone compound or salt thereof as described in any one of (23) to (44), wherein X is C(RA) or N, n is 1 or 2, and at least one Y is substituted in the para position relative to the pyridazinone ring. (52) A pyridazinone compound or a salt thereof as described in any one of (23) to (40) and (43) to (51), wherein R1, R2, R3 and R4 are each halogen, (C1-C4)alkyl, (C3-C6)cycloalkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfinyl, (C1-C4)alkylsulfonyl, cyano, nitro, -C(=O)RI or dimethoxymethyl. (53) A pyridazinone compound or a salt thereof as described in any one of (23) to (40) and (43) to (51), wherein R1, R2, R3 and R4 are each halogen, (C1-C4)alkyl, (C3-C6)cycloalkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, nitro or dimethoxymethyl. (54) A pyridazinone compound or a salt thereof as described in any one of (23) to (38) and (43) to (53), wherein Z is (C1-C5)alkyl, (C3-C4)cycloalkyl, (C1-C4)alkoxy, (C1-C4)alkyl or (C1-C4)haloalkyl. (55) The pyridazinone compound or its salt as described in any one of (23) to (54), wherein n is 1 or 2. (56) The pyridazinone compound or its salt as described in any one of (23) to (54), wherein n is 2.

[0265] (57) A pest control agent comprising a compound or a salt thereof as described in any one of (1) to (56) as an active ingredient. (58) An insecticide, acaricide, nematocide or soil insecticide comprising a compound or a salt thereof as described in any one of (1) to (56) as an active ingredient. (59) An insecticide comprising a compound or a salt thereof as described in any one of (1) to (56) as an active ingredient. (60) A method comprising applying an effective amount of a compound or a salt thereof as described in any one of (1) to (56) to control pests. [Examples]

[0266] Next, although examples of the present invention are described, the present invention is not limited thereto. First, a synthesis example of the compound of the present invention is described. Synthesis Example 1 Synthesis of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-6-ethyl-5-hydroxy-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridin-3(2H)-one (Compound No. 1-57 described below) (1) A mixture of 6-bromo-4,5-dichloropyridin-3(2H)-one (19.0 g, 77.9 mmol), 3,4-dihydro-2H-pyran (13.1 g, 156 mmol), p-toluenesulfonic acid monohydrate (1.48 g, 7.79 mmol), and tetrahydrofuran (130 mL) was heated and stirred at 80°C for 16 hours to react. After the reaction, the mixture was cooled to room temperature, and a saturated aqueous sodium bicarbonate solution was added. The resulting mixture was extracted with ethyl acetate, and the collected organic extracts were dried over sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 19.1 g (yield 75%) of 6-bromo-4,5-dichloro-2-(tetrahydro-2H-pyran-2-yl)pyridinium-3(2H)-one. The 1H-NMR spectral data are as follows: 1H-NMR (CDCl 3, 500 MHz): 5.95 (1H, dd), 4.07-4.15 (1H, m), 3.66-3.75 (1H, m), 1.97-2.25 (2H, m), 1.63-1.80 (4H, m)

[0268] (2) A mixture of 6-bromo-4,5-dichloro-2-(tetrahydro-2H-pyran-2-yl)thiazolin-3(2H)-one (2.0 g, 6.1 mmol), ethylboric acid (0.54 g, 7.3 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (0.50 g, 0.61 mmol), cesium carbonate (2.3 g, 7.0 mmol) and 1,4-dioxane (18 mL) was reacted under reflux with stirring for 16 hours. After the reaction, the mixture was ice-cooled and water was added. The resulting mixture was extracted with ethyl acetate, and the collected organic extract was dried over sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 1.1 g (yield 62%) of 4,5-dichloro-6-ethyl-2-(tetrahydro-2H-pyran-2-yl)pyridinium-3(2H)-one. The 1H-NMR spectral data are as follows: 1H-NMR (CDCl 3, 500 MHz): 6.00 (1H, dd), 4.05-4.20 (1H, m), 3.70-3.83 (1H, m), 2.77-2.87 (2H, m), 2.17-2.34 (1H, m), 1.95-2.13 (2H, m), 1.60-1.80 (4H, m), 1.28 (3H, t).

[0269] (3) To a solution of 4,5-dichloro-6-ethyl-2-(tetrahydro-2H-pyran-2-yl)pyran-3(2H)-one (3.9 g, 14 mmol) in ethanol (100 mL) was added concentrated hydrochloric acid (10 mL) at room temperature. The mixture was then stirred at 80°C for 2 hours while being heated to react. After the reaction, the mixture was cooled to room temperature and concentrated. Ethanol was added to the residue, and azeotropic dehydration was performed under reduced pressure to obtain 2.3 g of 4,5-dichloro-6-ethylpyran-3(2H)-one (yield 85%). The 1H-NMR spectral data are as follows. 1H-NMR (CDCl 3, 500 MHz): 10.47 (1H, brs), 2.80 (2H, q), 1.26 (3H, t)

[0270] (4) Sodium hydride (dispersed to about 60% liquid paraffin) (0.53 g, 13 mmol) was added little by little to a solution of 4,5-dichloro-6-ethylpyridamole-3(2H)-one (2.2 g, 11 mmol) in N,N-dimethylformamide (20 mL) at 0°C. After stirring at 0°C for 30 minutes, 3-chloro-2-fluoro-5-(trifluoromethyl)pyridine (2.7 g, 13 mmol) was added. The mixture was then stirred at room temperature for 4 hours to react. After the reaction, water was added. The resulting mixture was extracted with ethyl acetate, and the collected organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 2.9 g (70% yield) of 4,5-dichloro-2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-6-ethylpyridin-3(2H)-one. The 1H-NMR spectral data are as follows: 1H-NMR (CDCl 3, 500 MHz): 8.81 (1H, d), 8.18 (1H, d), 2.87 (2H, q), 1.27 (3H, t).

[0271] (5) Sodium hydride (dispersed in about 60% liquid paraffin) (0.45 g, 11 mmol) was added little by little to a solution of 3-(trifluoromethyl)pyrazole (1.5 g, 11 mmol) in N,N-dimethylformamide (21 mL) at 0°C. After stirring at 0°C for 30 minutes, 4,5-dichloro-2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-6-ethylpyridin-3(2H)-one (2.0 g, 5.4 mmol) was added. The mixture was then stirred at 60°C for 2 hours to react. After the reaction, the mixture was cooled to room temperature, and a 1N aqueous sodium hydroxide solution (7 mL, 7 mmol) was added to the resulting reaction mixture, which was then stirred at 60°C for 1 hour to react. After the reaction, the mixture was cooled to room temperature, and the solution was adjusted to acidity by adding 1N hydrochloric acid. The resulting mixture was extracted with ethyl acetate, and the collected organic extracts were dried over sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 1.4 g (yield 57%) of the target compound.

[0272] Synthesis Example 2 Synthesis of 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-6-ethyl-5-hydroxy-4-(3-nitro-1H-1,2,4-triazol-1-yl)thiazol-3(2H)-one (Compound No. 6-65 described later) (1) A mixture of 3-nitro-1H-1,2,4-triazole (1.0 g, 8.77 mmol), methyl bromoacetate (1.88 g, 12.3 mmol), potassium carbonate (2.18 g, 15.78 mmol), and acetonitrile (15 mL) was heated and stirred at 80°C for 4 hours to react. After the reaction, the mixture was cooled to room temperature, ethyl acetate was added, and the mixture was filtered. 1N hydrochloric acid was added to the filtrate, and the resulting mixture was extracted with ethyl acetate. The collected organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to yield 1.95 g of crude methyl 2-(3-nitro-1H-1,2,4-triazol-1-yl)acetate. The 1H-NMR spectral data are as follows: 1H-NMR (CDCl 3, 500 MHz): 8.21 (1H, s), 5.10 (2H, s), 3.86 (3H, s)

[0273] (2) A solution of methyl 2-(3-nitro-1H-1,2,4-triazol-1-yl)acetate (1.31 g, 7.04 mmol) in tetrahydrofuran (10 mL) was added with a solution of sodium hydroxide (0.60 g, 15 mmol) in water (5 mL), and the mixture was stirred at room temperature for 3 hours to react. After the reaction, heptane was added, and the resulting mixture was extracted twice with water. Concentrated hydrochloric acid was added to the collected aqueous layer to adjust the acidity, and the resulting mixture was extracted with ethyl acetate. The collected organic extract was washed with saturated brine and dried over anhydrous sodium sulfate. Then, the mixture was filtered and concentrated to obtain 1.32 g of crude 2-[3-nitro-1H-1,2,4-triazol-1-yl]acetic acid. The 1H-NMR spectrum data of this product are as follows. 1H-NMR (DMSO-d 6, 500 MHz): 8.86 (1H, s), 5.30 (2H, s)

[0274] (3) A solution of sodium nitrite (1.10 g, 15.94 mmol) in water (12 mL) was added to a solution of 2,6-dimethyl-4-(trifluoromethyl)phenylaniline (2.49 g, 13.16 mmol) in concentrated hydrochloric acid (12 mL) at 0°C, and the mixture was stirred at the same temperature for 1 hour to prepare a diazonium salt aqueous solution. Alternatively, tin (II) chloride dihydrate (8.91 g, 15.5 mmol) was dissolved in concentrated hydrochloric acid (28 mL), and the diazonium salt aqueous solution was added dropwise at room temperature. After the addition, the mixture was stirred at room temperature for 16 hours to react. After the reaction, heptane was added, the mixture was filtered, and ethanol was added to the resulting solid, and the mixture was azeotropically dehydrated under reduced pressure to obtain 2.84 g (yield 90%) of a crude product of [2,6-dimethyl-4-(trifluoromethyl)phenyl]hydrazine hydrochloride. The 1H-NMR spectrum data of the crude product are as follows. 1H-NMR (DMSO-d 6, 500 MHz): 9.77 (3H, br), 7.46 (2H, s), 6.96 (1H, br), 2.43 (6H, s)

[0275] (4) [2,6-dimethyl-4-(trifluoromethyl)phenyl]hydrazine hydrochloride (2.00 g, 8.31 mmol) and triethylamine (4.63 mL, 33.2 mmol) were dissolved in dichloromethane (21 mL), and (Boc) 2O (3.63 g, 33.2 mmol) was added at 0°C. Then, the mixture was stirred at room temperature for 12 hours to react. After the reaction, 2,2,2-trifluoroethanol (0.10 g, 0.83 mmol) and 4-dimethylaminopyridine (0.10 g, 0.83 mmol) were added. The mixture was stirred at room temperature for 1 hour to react. After the reaction, the mixture was concentrated to obtain a residue. Ethyl acetate and 1N hydrochloric acid were added to the obtained residue, and the obtained mixture was extracted with ethyl acetate. The collected organic extract was washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 1.76 g (yield: 70%) of tert-butyl 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]hydrazine-1-carboxylate. The 1H-NMR spectral data are as follows: 1H-NMR (CDCl 3, 500 MHz): 7.22 (2H, s), 6.34 (1H, br), 5.83 (1H, d), 2.40 (6H, s), 1.40 (9H, brs).

[0276] (5) 2-(3-nitro-1H-1,2,4-triazol-1-yl)acetic acid (0.23 g, 0.76 mmol) and N,N-dimethylformamide (10 mg, 0.14 mmol) were dissolved in dichloromethane (4 mL), and ethylenediamine chloride (0.50 mL, 5.71 mmol) was added and reacted while stirring at room temperature for 1 hour. After the reaction, the mixture was concentrated under reduced pressure to obtain the acyl chloride. Alternatively, potassium carbonate (0.18 g, 1.31 mmol) was added to a solution of tert-butyl 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]hydrazine-1-carboxylate (0.20 g, 0.66 mmol) in dichloromethane (2 mL) at 0°C. After stirring at 0°C for 10 minutes, the above-mentioned solution of the acyl chloride in dichloromethane (2 mL) was added dropwise. After the addition, the mixture was stirred at 0°C for 10 minutes, then heated and allowed to react at room temperature for 21 hours. After the reaction, ethyl acetate and water were added, and the resulting mixture was extracted with ethyl acetate. The collected organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 0.13 g (yield 38%) of tert-butyl 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-2-[2-(3-nitro-1H-1,2,4-triazol-1-yl)acetyl]hydrazine-1-carboxylate. The 1H-NMR spectral data are shown below. 1H-NMR (CDCl 3, 500MHz): 8.39 (1H, s), 8.38 (0.6H, s), 7.48 (1.2H, s), 7.39 (2H, s), 6.79 (1H, s), 6.78 (0.6H, s), 5.10-5.80 (2H, m), 4.75 (1.2H, s), 2.53 (3.6H, s), 2.39 (6H, br), 1.49 (9H, s), 1.47 (5.4H, s)

[0277] (6) To a solution of tert-butyl 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-2-[2-(3-nitro-1H-1,2,4-triazol-1-yl)acetyl]hydrazine-1-carboxylate (0.13 g, 0.29 mmol) in dichloromethane (4 mL) was added a solution of trifluoroacetic acid (1.00 mL, 13 mmol) in dichloromethane (1 mL), and the mixture was stirred at room temperature for 1 hour to react. After the reaction, a saturated aqueous sodium bicarbonate solution was added, and the resulting mixture was extracted with ethyl acetate. The collected organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. p-Toluenesulfonic acid monohydrate (10 mg, 0.05 mmol), methanol (5 mL), and methyl 2-oxobutanoate (50 mg, 0.43 mmol) were added to the resulting residue in this order, and the mixture was stirred at 70°C for 30 minutes to react. After the reaction, the mixture was cooled to room temperature and concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 95 mg (yield: 73%) of methyl 2-{2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-2-[2-(3-nitro-1H-1,2,4-triazol-1-yl)acetyl]hydrazono}butanoate. The 1H-NMR spectral data are shown below. 1H-NMR (CDCl 3, 500MHz): 8.38 (0.6H, s), 8.36 (1H, s), 7.42 (1.2H, s), 7.34 (2H, s), 5.78 (1.2H, s), 5.77 (2H, s), 3.88 (1.8H, s), 3.09 (3H, s), 2.51 (2H, q), 2.20 (3.6H, s), 2.17 (6H, s), 1.91 (1.2H, q), 1.20 (3H, t), 0.67 (1.8H, t)

[0278] (7) To a solution of methyl 2-{2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-2-[2-(3-nitro-1H-1,2,4-triazol-1-yl)acetyl]hydrazono}butanoate (94 mg, 0.21 mmol) in acetonitrile (4 mL) was added 1,8-diazacyclo[5.4.0]-7-undecene (0.10 mL, 0.66 mmol), and the mixture was stirred at 70°C for 30 minutes to react. After the reaction, the mixture was cooled to room temperature, ethyl acetate and water were added, and then 2N hydrochloric acid was added to adjust the solution to acidity. The resulting mixture was extracted with ethyl acetate. The collected organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 24 mg (yield 27%) of the desired product.

[0279] Synthesis Example 3 Synthesis of 2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-6-ethyl-5-hydroxy-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridinium-3(2H)-one (Compound No. 2-97 described below) (1) To a solution of sodium hydroxide (2.12 g, 52.9 mmol) in water (30 mL), 3-(trifluoromethyl)pyrazole (3.00 g, 22.1 mmol) and bromoacetic acid (3.22 g, 23.2 mmol) were added in sequence. The mixture was then stirred at 100°C for 15 hours to allow the reaction to proceed. After the reaction, the mixture was cooled to 0°C, 2N hydrochloric acid was added to acidify the solution, and n-heptane was then added. The precipitated solid was recovered by filtration to obtain 3.41 g (80% yield) of crude 2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid. The 1H-NMR spectral data are as follows: 1H-NMR (CDCl 3 , 500 MHz): 7.55 (1H, d), 6.62 (1H, d), 5.04 (2H, s)

[0280] (2) A mixture of [2,6-dichloro-4-(trifluoromethyl)phenyl]hydrazine (500 mg, 2.04 mmol), methyl 2-oxobutanoate (284 mg, 2.45 mmol) and methanol (10 mL) was heated and stirred at 65°C for 15 hours to react. After dilution with ethyl acetate, water was added. The resulting mixture was extracted with ethyl acetate, and the collected organic extract was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 526 mg of methyl 2-{2-[2,6-dichloro-4-(trifluoromethyl)phenyl]hydrazono}butanoate (yield 75%). The 1H-NMR spectrum data are as follows. 1H-NMR (CDCl 3, 500MHz): 12.28 (1H, s), 7.54 (2H, s), 3.86 (3H, s), 2.57 (2H, q), 1.16 (3H, t) (3) A mixture of 2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid (357 mg, 1.84 mmol), N,N-dimethylformamide (10 mg, 0.14 mmol), and dichloromethane (10 mL) was stirred in an ice bath for several minutes, and then ethylenediamine chloride (0.17 mL, 1.99 mmol) was slowly added dropwise. After the addition was complete, the mixture was stirred at room temperature for 3 hours and then concentrated under reduced pressure to obtain the acyl chloride. Alternatively, a mixture of methyl 2-{2-[2,6-dichloro-4-(trifluoromethyl)phenyl]hydrazono}butanoate (526 mg, 1.53 mmol) and tetrahydrofuran (15 mL) was stirred in an ice bath under a nitrogen atmosphere for several minutes. A solution of lithium hexamethyldisilazane in tetrahydrofuran (2.95 mL, 1.3 molar, 3.83 mmol) was then added and stirred for 45 minutes. After the mixture was adjusted, the acyl chloride described above was added. The reaction was then allowed to stir at room temperature for 16 hours. 2N hydrochloric acid was added to acidify the solution, water was added, and the mixture was extracted with ethyl acetate. The collected organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by silica gel chromatography (eluent: ethyl acetate / n-heptane) to obtain 82 mg (yield 11%) of the desired compound.

[0282] Synthesis Example 4 Synthesis of 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-6-ethyl-5-hydroxy-4-(3-cyano-1H-1,2,4-triazol-1-yl)pyrimidine-3(2H)-one (Compound No. 6-60 described below) (1) To a solution of tert-butyl 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]hydrazine-1-carboxylate (0.50 g, 1.64 mmol) in dichloromethane (11 mL) was added potassium carbonate (0.45 g, 3.29 mmol) at room temperature. After stirring at room temperature for 10 minutes, bromoacetyl bromide (0.17 mL, 1.97 mmol) was added dropwise at 0°C. After the addition, the mixture was stirred at 0°C for 30 minutes, then heated and allowed to react while stirring at room temperature for 21 hours. After the reaction, ethyl acetate and water were added, and the resulting mixture was extracted with ethyl acetate. The collected organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 0.34 g (yield 49%) of tert-butyl 2-(2-bromoacetyl)-2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]hydrazine-1-carboxylate. The 1H-NMR spectral data are shown below. 1H-NMR (CDCl 3, 300MHz): 7.42 (1.4H, s), 7.35 (2H, s), 6.97 (1H, s), 6.77 (0.7H, s), 4.05 (2H, s), 3.64 (1.4H, s), 2.49 (4.2H, s), 2.42 (6H, s), 1.48 (6.3H, s), 1.47 (9H, s)

[0283] (2) To a solution of 3-cyano-1H-1,2,4-triazole (50 mg, 0.57 mmol) in N,N-dimethylformamide (3 mL) was added potassium carbonate (0.16 g, 1.14 mmol) at room temperature. After stirring at room temperature for 30 minutes, a solution of tert-butyl 2-(2-bromoacetyl)-2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]hydrazine-1-carboxylate (0.22 g, 0.52 mmol) in N,N-dimethylformamide (3 mL) was added dropwise. After the addition, the mixture was stirred at room temperature for 17 hours to react. After the reaction, ethyl acetate and water were added, and the resulting mixture was extracted with ethyl acetate. The collected organic extract was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 0.17 g (yield: 75%) of tert-butyl 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-2-[2-(3-cyano-1H-1,2,4-triazol-1-yl)acetyl]hydrazine-1-carboxylate. The 1H-NMR spectral data are shown below. 1H-NMR (CDCl 3, 300MHz): 8.39 (1H, s), 8.35 (0.9H, s), 7.49 (1.8H, s), 7.41 (2H, s), 6.83 (1H, s), 6.77 (0.9H, s), 5.48 (2H, brs), 4.71 (1.8H, s), 2.53 (5.4H, s), 2.39 (6H, brs), 1.49 (9H, s), 1.48 (8.1H, s)

[0284] (3) According to the description of (6) and (7) of Synthesis Example 2, the target compound 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-6-ethyl-5-hydroxy-4-(3-cyano-1H-1,2,4-triazol-1-yl)acetyl]hydrazine-1-carboxylic acid tert-butyl ester was synthesized.

[0285] Synthesis Example 5 Synthesis of 4-(3-chloro-1H-pyrazol-1-yl)-2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-5-hydroxy-6-(methoxymethyl)pyridinium-3(2H)-one (Compound No. 2-444 described below) (1) A mixture of ethyl 5-(3-chloro-1H-pyrazol-1-yl)-1-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-4-hydroxy-6-oxo-1,6-dihydropyridinium-3-carboxylate (0.40 g, 0.88 mmol) prepared according to Synthesis Example 2, lithium aluminum hydride (0.10 g, 2.63 mmol) and tetrahydrofuran (18 mL) was reacted at 0°C with stirring for 3 hours. After the reaction, ethyl acetate and water were added, and the resulting mixture was extracted with an aqueous sodium hydroxide solution. The collected aqueous layer was acidified by adding 2N hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The collected organic extract was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to yield 0.35 g of crude 4-(3-chloro-1H-pyrazol-1-yl)-2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-5-hydroxy-6-(hydroxymethyl)thiazol-3(2H)-one. The 1H-NMR spectral data are as follows: 1H-NMR (CDCl 3, 300 MHz): 13.06 (1H, brs), 9.23 (1H, d), 7.49 (2H, s), 6.48 (1H, d), 4.85 (2H, s), 2.18 (6H, s)

[0286] (2) To a solution of 4-(3-chloro-1H-pyrazol-1-yl)-2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-5-hydroxy-6-(hydroxymethyl)pyrimidine-3(2H)-one (0.27 g, 0.66 mmol) in N,N-dimethylformamide (4 mL) was added sodium hydride (dispersed in about 60% liquid paraffin) (0.10 g, 2.62 mmol) and methyl iodide (0.37 g, 2.62 mmol) at ℃. The mixture was then stirred at room temperature for 15 hours to react. A 2N aqueous sodium hydroxide solution was added to the resulting reaction mixture, and the mixture was stirred at room temperature for 1 hour to react. After dilution with ethyl acetate, 0.5N hydrochloric acid was added. The resulting mixture was extracted with ethyl acetate. The collected organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 87 mg (yield 31%) of the desired product.

[0287] Synthesis Example 6 Synthesis of 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-5-hydroxy-4-(3-methyl-1H-pyrazol-1-yl)-6-(trifluoromethyl)pyrimidine-3(2H)-one (Compound No. 2-516 described below) (1) 4-(3-bromo-1H-pyrazol-1-yl)-2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-5-hydroxy-6-( (trifluoromethyl)-3(2H)-one (81 mg, 0.16 mmol), trimethylboroxine (0.11 mL, 0.81 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (13 mg, 0.020 mmol), and potassium carbonate (68 mg, 0.49 mmol) were dissolved in water (2 mL) and 1,4-dioxane (4 mL). The mixture was stirred at 140°C for 6 hours while being heated in a microwave synthesis apparatus. After the reaction, it was cooled to room temperature. After the addition of water and 1N hydrochloric acid, ethyl acetate was added, and the mixture was filtered through celite. The resulting filtrate mixture was extracted with ethyl acetate. The collected organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 46 mg (yield 65%) of the desired product.

[0288] Synthesis Example 7 Synthesis of 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-4-(3-ethyl-1H-1,2,4-triazol-1-yl)-5-hydroxy-6-isopropylpyridamole-3(2H)-one (Compound No. 6-134 described below) (1) 4-(3-bromo-1H-1,2,4-triazol-1-yl)-2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-5-hydroxy-6-isopropylpyridamole-3(2H)-one prepared according to the description of Synthesis Example 2 was used. 3(2H)-ketone (50 mg, 0.11 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (50 mg, 0.32 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (8.7 mg, 0.011 mmol), and potassium carbonate (40 mg, 0.32 mmol) were dissolved in water (0.5 mL) and 1,4-dioxane (1 mL). The mixture was stirred at 140°C for 6 hours while being heated using a microwave synthesis apparatus. After the reaction, the mixture was allowed to cool to room temperature. After the addition of water and 1N hydrochloric acid, ethyl acetate was added, and the mixture was filtered through celite. The resulting filtrate mixture was extracted with ethyl acetate. The collected organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 30 mg (yield 68%) of 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-5-hydroxy-6-isopropyl-4-(3-vinyl-1H-1,2,4-triazol-1-yl)thiazol-3(2H)-one. The 1H-NMR spectral data are shown below. 1H-NMR (CDCl 3, 500MHz): 12.86 (1H, brs), 9.77 (1H, s), 7.46 (2H, s), 6.78 (1H, dd), 6.45 (1H, d), 5.74 (1H, d), 3.42 (1H, sep), 2.15 (6H, s), 1.28 (6H, d)

[0289] (2) To a solution of 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-5-hydroxy-6-isopropyl-4-(3-vinyl-1H-1,2,4-triazol-1-yl)triazol-3(2H)-one (30 mg, 0.070 mmol) in ethanol (1.4 mL) was added 5% palladium-carbon (water-containing product) (7 mg), and the mixture was stirred at room temperature for 12 hours to react. After the reaction, ethyl acetate was added, and the mixture was filtered through celite. The filtrate was concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: ethanol / ethyl acetate) to obtain 20 mg of the target compound (yield 66%).

[0290] Synthesis Example 8 Synthesis of 4-[5-(3-chloro-1H-1,2,4-triazol-1-yl)-3-ethyl-4-hydroxy-6-oxopyridin-1(6H)-yl]-3,5-dimethylbenzonitrile (Compound No. 6-136 described below) (1) A mixture of methyl 4-[5-(3-chloro-1H-1,2,4-triazol-1-yl)-3-ethyl-4-hydroxy-6-oxopyridin-1(6H)-yl]-3,5-dimethylbenzoate (91 mg, 0.23 mmol), lithium aluminum hydride (21 mg, 0.56 mmol), and tetrahydrofuran (4 mL) prepared according to Synthesis Example 2 was stirred at -10°C for 3 hours to react. The resulting reaction mixture was added to a funnel filled with celite and silica gel, and ethyl acetate and 2N hydrochloric acid were added, followed by filtration. The filtrate was diluted with ethyl acetate, and water was added. The resulting mixture was extracted with ethyl acetate. The collected organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain 88 mg of the crude product 4-(3-chloro-1H-1,2,4-triazol-1-yl)-6-ethyl-5-hydroxy-2-[4-(hydroxymethyl)-2,6-dimethylphenyl]phthalim-3(2H)-one. The 1H-NMR spectral data are as follows: 1H-NMR (CDCl 3, 300 MHz): 11.86 (1H, brs), 9.81 (1H, s), 7.21 (2H, s), 4.68 (2H, s), 2.87 (2H, q), 2.10 (6H, s), 1.29 (3H, t)

[0291] (2) Activated manganese dioxide (0.59 g, 6.79 mmol) was added to a solution of 4-(3-chloro-1H-1,2,4-triazol-1-yl)-6-ethyl-5-hydroxy-2-[4-(hydroxymethyl)-2,6-dimethylphenyl]phthalimide-3(2H)-one (85 mg, 0.23 mmol) in dichloromethane (5 mL), and the mixture was stirred at room temperature for 22 hours to react. After filtration through celite, the filtrate was concentrated to obtain 79 mg of a crude product, 4-[5-(3-chloro-1H-1,2,4-triazol-1-yl)-3-ethyl-4-hydroxy-6-oxopitamidin-1(6H)-yl]-3,5-dimethylbenzaldehyde. The 1H-NMR spectrum data are as follows. 1H-NMR (CDCl 3, 300MHz): 11.93 (1H, brs), 10.04 (1H, s), 9.78 (1H, s), 7.74 (2H, s), 2.88 (2H, q), 2.20 (6H, s), 1.30 (3H, t)

[0292] (3) 4-[5-(3-chloro-1H-1,2,4-triazol-1-yl)-3-ethyl-4-hydroxy-6-oxopyrazol-1(6H)-yl]-3,5-dimethylbenzaldehyde (79 mg, 0.21 mmol) and diisopropylethylamine (54 mg, 0.42 mmol) were dissolved in tetrahydrofuran (4 mL), and isobutylyl chloride (36 mg, 0.34 mmol) was added. Then, the mixture was stirred at room temperature for 16 hours and allowed to react. After dilution with ethyl acetate, water was added. The resulting mixture was extracted with ethyl acetate. The collected organic extract was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 75 mg (80% yield) of 4-[5-(3-chloro-1H-1,2,4-triazol-1-yl)-3-ethyl-4-isobutyryloxy-6-oxopyrithione-1(6H)-yl]-3,5-dimethylbenzaldehyde. The 1H-NMR spectral data are as follows: 1H-NMR (CDCl 3 , 300 MHz): 10.05 (1H, s), 9.20 (1H, s), 7.75 (2H, s), 2.99 (1H, sep), 2.76 (2H, q), 2.22 (6H, s), 1.40 (6H, d), 1.27 (3H, t).

[0293] (4) 4-[5-(3-chloro-1H-1,2,4-triazol-1-yl)-3-ethyl-4-isobutyryloxy-6-oxopyrazol-1(6H)-yl]-3,5-dimethylbenzaldehyde (75 mg, 0.17 mmol) and sodium acetate (14 mg, 0.17 mmol) were dissolved in tetrahydrofuran (1 mL) and ethanol (3 mL), and hydroxylamine (50% aqueous solution) (56 mg, 0.85 mmol) was added. Then, the mixture was stirred at room temperature for 20 hours and allowed to react. 2N aqueous sodium hydroxide solution (2 mL) was added to the resulting reaction mixture, and after stirring at room temperature for 15 minutes, ethyl acetate and heptane were added. Water was added for extraction, and 2N hydrochloric acid was added to the collected aqueous layer to adjust the mixture to acidity. The resulting mixture was extracted with ethyl acetate. The collected organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to yield 69 mg of crude (E)-4-[5-(3-chloro-1H-1,2,4-triazol-1-yl)-3-ethyl-4-hydroxy-6-oxopyridin-1(6H)-yl]-3,5-dimethylbenzaldehyde oxime. The 1H-NMR spectral data are as follows: 1H-NMR (CDCl 3 , 300 MHz): 11.90 (1H, br s), 9.81 (1H, s), 8.13 (1H, s), 7.43 (2H, s), 2.88 (2H, q), 2.14 (6H, s), 1.30 (3H, t).

[0294] (5) A mixture of (E)-4-[5-(3-chloro-1H-1,2,4-triazol-1-yl)-3-ethyl-4-hydroxy-6-oxopyrazol-1(6H)-yl]-3,5-dimethylbenzaldehyde oxime (69 mg, 0.18 mmol) and acetic anhydride (5 mL) was heated and stirred at 140°C for 16 hours to react. After the reaction, the mixture was cooled to room temperature and diluted with ethyl acetate and water. The resulting mixture was extracted with ethyl acetate. The collected organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain a mixture containing the target compound. A 2N sodium hydroxide aqueous solution (2 mL) was added to a tetrahydrofuran (2 mL) solution of the mixture, and the mixture was stirred at room temperature for 2 hours to react. 1N hydrochloric acid was added to make the mixture acidic, and the resulting mixture was extracted with ethyl acetate. The collected organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain 22 mg of the desired product (yield 33%).

[0295] Synthesis Example 9 Synthesis of 4-(3-chloro-1H-pyrazol-1-yl)-2-{2,6-dimethyl-4-[(trifluoromethyl)sulfonyl]phenyl}-6-ethyl-5-hydroxypyridinium-3(2H)-one (Compound No. 2-191 described below) (1) 4-(3-chloro-1H-pyrazol-1-yl)-2-{2,6-dimethyl-4-[(trifluoromethyl)thio]phenyl}-6-ethyl-5-hydroxypyridinium-3(2H)-one (70 mg, 0.16 mmol) prepared according to Synthesis Example 2 was dissolved in diisopropylethylamine (31 mg, 0.24 mmol) and tetrahydrofuran (4 mL), and isobutylyl chloride (20 mg, 0.19 mmol) was added. The mixture was stirred at room temperature for 3 hours and allowed to react. After dilution with ethyl acetate, water was added. The resulting mixture was extracted with ethyl acetate. The collected organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 80 mg (yield 99%) of 4-(3-chloro-1H-pyrazol-1-yl)-2-{2,6-dimethyl-4-[(trifluoromethyl)thio]phenyl}-6-ethyl-5-(isobutyryloxy)thiazol-3(2H)-one. The 1H-NMR spectral data are shown below. 1H-NMR (CDCl 3, 300MHz): 8.43 (1H, d), 7.49 (2H, s), 6.35 (1H, d), 2.94 (1H, sep), 2.71 (2H, q), 2.13 (6H, s), 1.35 (6H, d), 1.24 (3H, t)

[0296] (2) A mixture of 4-(3-chloro-1H-pyrazol-1-yl)-2-{2,6-dimethyl-4-[(trifluoromethyl)thio]phenyl}-6-ethyl-5-(isobutyryloxy)thiazol-3(2H)-one (35 mg, 0.070 mmol), 72% m-chloroperbenzoic acid (water product) (33 mg, 0.14 mmol) and dichloroethane (1 mL) was heated and stirred at 50°C for 16 hours to react. After the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate, and then a 0.1N sodium hydroxide aqueous solution was added. The resulting mixture was extracted with ethyl acetate. The collected organic extract was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 38 mg (yield 102%) of 4-(3-chloro-1H-pyrazol-1-yl)-2-{2,6-dimethyl-4-[(trifluoromethyl)sulfonyl]phenyl}-6-ethyl-5-(isobutyryloxy)pyridinium-3(2H)-one. The 1H-NMR spectral data are as follows: 1H-NMR (CDCl 3, 300 MHz): 8.41 (1H, d), 7.87 (2H, s), 6.37 (1H, d), 2.96 (1H, sep), 2.72 (2H, q), 2.24 (6H, s), 1.36 (6H, d), 1.24 (3H, t).

[0297] (3) A 2N aqueous sodium hydroxide solution (2 mL) was added to a solution of 4-(3-chloro-1H-pyrazol-1-yl)-2-{2,6-dimethyl-4-[(trifluoromethyl)sulfonyl]phenyl}-6-ethyl-5-(isobutyryloxy)pyrimidine-3(2H)-one (38 mg, 0.070 mmol) in tetrahydrofuran (2 mL), and the mixture was stirred at room temperature for 1 hour to react. 2N hydrochloric acid was added to adjust the acidity, and the resulting mixture was extracted with ethyl acetate. The collected organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / n-heptane) to obtain 29 mg of the target compound (yield 88%).

[0298] Synthesis Example 10 Preparation of tetrabutylammonium salt of 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-6-ethyl-4-(4-fluoro-1H-pyrazol-1-yl)-5-hydroxypyridinium-3(2H)-one (Compound No. 2-555 described later) (1) To a solution of 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-6-ethyl-4-(4-fluoro-1H-pyrazol-1-yl)-5-hydroxypyridinium-3(2H)-one (50 mg, 0.13 mmol) in tetrahydrofuran (4 mL) was added tetrabutylammonium hydroxide (10% methanol solution) (0.67 g, 0.26 mmol), and the mixture was stirred at room temperature for 2 hours to react. After concentrating the resulting mixture, tert-butyl methyl ether was added and the mixture was filtered. Ethyl acetate was then added to the recovered solid and the mixture was filtered. The obtained solid was dried to obtain 28 mg (yield 35%) of the target compound.

[0299] Next, representative examples of the compounds of formula (I) are listed in Tables 1 to 8. These compounds can be synthesized according to the aforementioned synthesis examples or the aforementioned various production methods. In addition, as physical properties of representative examples of the compounds of formula (I), 1H-NMR spectrum data are shown in Table 9. In the 1H-NMR spectrum data in Table 9, s represents a singlet, brs represents an expanded singlet, d represents a doublet, t represents a triplet, q represents a quadruple, quin represents a quintet, sep represents a septet, m represents a multiplet, and br represents a broad. In each table, No. represents the compound number. In addition, the abbreviations used in Tables 1 to 8 represent the following substituents: Me represents a methyl group, Et represents an ethyl group, nPr represents an n-propyl group, iPr represents an isopropyl group, nBu represents an n-butyl group, sBu represents a sec-butyl group, tBu represents a tert-butyl group, cPr represents a cyclopropyl group, cBu represents a cyclobutyl group, cPen represents a cyclopentyl group, cHex represents a cyclohexyl group, DXAN represents a 1,3-dioxan-2-yl group, and DXOL represents a 1,3-dioxolan-2-yl group. For example, in the tables, "OMe" represents a methoxy group, "SMe" represents a methylthio group, and "OcPr" represents a cyclopropyloxy group. In Table 1, for example, a compound described as "3-CF3" in the (R1)a column indicates that the "3" position of the pyrazole ring represented by the chemical formula in the table is substituted with CF3, that is, a compound described as "a=1" in which the 3-position of the pyrazole ring is substituted with one R1. Furthermore, in Table 1, a compound described as "a=0" in the (R1)a column indicates that R1 is unsubstituted, and a compound described as "n=0" in the (Y)n column indicates that Y is unsubstituted. The same applies to other similar descriptions in Tables 1 through 8. Furthermore, in Table 2, compounds with "*" appended to the compound number indicate salts of the compound of Formula (I). A description of the salt is given outside the column of Table 2.

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391] Test Example 1 Effect test on brown planthoppers: Rice seedlings were immersed in a solution prepared in such a way that the concentration of the test compound became 200ppm or 50ppm. After the solution was air-dried, the roots were wrapped with moistened cotton wool and placed in a test tube. About 10 2nd to 3rd instar larvae of brown planthoppers were released into the tube, the tube mouth was covered with gauze, and the tube was placed in a constant temperature room with lighting at 25°C. After 5 days of treatment, the life and death of the brown planthoppers was determined, and the mortality rate (%) was calculated using the following calculation formula. [Calculation formula] Mortality rate (%) = (number of dead insects / number of released insects) × 100 As a result, the aforementioned compounds No. 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-10, 1-11, 1-12, 1-13, 1-25, 1-42, 1-43, 1-45, 1-46, 1-47, 1-48, 1-49, 1-51, 1-52, 1-57, 1-58, 1-60, 1-61, 1-63, 1-64, 1-65, 1-66, 1-68, 1-69, 1-70, 1-71, 1-73, 1-74, 1-76, 1-77, 1-78, 1 -80, 1-87, 1-100, 1-101, 1-103, 1-104, 1-105, 1-106, 1-107, 1-109, 1-110, 1-111, 1-113, 1-115, 1-116, 1-118, 1-128, 1-129, 1-130, 1-131, 1-132, 1-133, 1-135, 1-136, 1-138, 1-139, 1-140, 1-144, 1-146, 1-147, 1-148, 1-149, 1-150, 1-151, 1-152, 1-155, 1-156, 1-157, 1-158, 1-160, 1-161, 1-162, 1-163, 1-164, 1-165, 1-166, 1-167, 1-168, 1-170, 1-171, 1-175, 1-176, 1-177, 1-178, 1-179, 1-180, 1-181, 1-182, 1-183, 1-184, 1-186, 1-187, 1-188, 1-189, 1-190, 1-191, 1-192, 1-1 95, 1-196, 1-197, 1-198, 1-199, 1-201, 1-204, 1-205, 1-206, 1-207, 1-208, 1-209, 1-210, 1-212, 1-213, 1-214, 1-215, 1-216, 1-217, 1-218, 1-219, 1-220, 1-221, 1-222, 1-223, 1-224, 1-225, 1-233, 1-235, 1-236, 1-237, 1-239, 1-240, 1-241,1-242、1-244、1-245、1-246、1-247、1-249、1-250、1-251、1-252、1-253、1-256、1-257、1-258、1-259、1-260、1-261、1-262、1-263、1-264、1-267、1-270、1-273、1-274、1-275、1-276、1-277、1-278、1-282、1-283、1-284、1-285、1-286、1-287、1-289、1-291、1-292、1-293、1-294、1-295、1-296、1-297、1-298、1-299、1-300、1-301、2-1、2-3、2-6、2-8、2-9、2-10、2-12、2-13、2-14、2-15、2-18、2-19、2-20、2-23、2-24、2-25、2-26、2-27、2-28、2-29、2-32、2-36、2-37、2-38、2-40、2-41、2-42、2-43、2-44、2-45、2-46、2-47、2-48、2-49、2-52、2-54、2-55、2-56、2-58、2-59、2-60、2-62、2-63、2-64、2-66、2-67、2-69、2-70、2-71、2-74、2-76、2-77、2-78、2-79、2-80、2-81、2-83、2-85、2-86、2-87、2-88、2-89、2-91、2-92、2-93、2-94、2-96、2-97、2-98、2-99、2-100、2-101、2-102、2-103、2-104、2-105、2-106、2-107、2-109、2-111、2-112、2-114、2-115、2-116、2-117、2-118、2-119、2-120、2-121、2-122、2-123、2-126、2-127、2-128、2-129、2-130、2-131、2-133、2-136、2-137、2-139、2-140、2-143、2-144、2-147、2-149、2-151、2-153、2-154、2-167、2-168、2-169、2-171、2-172、2-173、2-175、2-177、2-178、2-179、2-180、2-181、2-182、2-183、2-184、2-185、2-186、2-190、2-191、2-192、2-195、2-197、2-198、2-206、2-207、2-209、2-215、2-218、2-222、2-224、2-234、2-235、2-236、2-237、2-238、2-239、2-240、2-241、2-243、2-262、2-263、2-266、2-270、2-271、2-274、2-277、2-278、2-279、2-283、2-284、2-285、2-286、2-287、2-288、2-291、2-292、2-293、2-294、2-295、2-296、2-297、2-298、2-299、2-300、2-301、2-302、2-303、2-304、2-309、2-310、2-311、2-313、2-314、2-317、2-318、2-319、2-323、2-324、2-325、2-326、2-328、2-329、2-335、2-336、2-338、2-340、2-342、2-345、2-347、2-348、2-349、2-352、2-353、2-356、2-357、2-359、2-360、2-362、2-364、2-365、2-366、2-369、2-373、2-377、2-378、2-379、2-380、2-381、2-382、2-383、2-384、2-385、2-386、2-387、2-388、2-389、2-390、2-393、2-394、2-395、2-396、2-398、2-399、2-401、2-403、2-404、2-406、2-407、2-408、2-409、2-413、2-414、2-415、2-422、2-423、2-424、2-426、2-428、2-429、2-430、2-431、2-432、2-433、2-434、2-435、2-436、2-437、2-438、2-439、2-441、2-444、2-446、2-447、2-448、2-449、2-450、2-451、2-452、2-453、2-454、2-455、2-456、2-457、2-458、2-459、2-460、2-461、2-462、2-463、2-464、2-465、2-466、2-467、2-468、2-469、2-470、2-471、2-472、2-473、2-474、2-475、2-476、2-477、2-478、2-479、2-480、2-481、2-482、2-483、2-484、2-485、2-487, 2-488, 2-489, 2-490, 2-493, 2-494, 2-495, 2-496, 2-497, 2-498, 2-500, 2-501, 2-502, 2-503, 2-504, 2-505, 2-506, 2-507, 2-508, 2-509, 2-510, 2-511, 2-512, 2-513, 2-514, 2-515, 2-516, 2-517, 2-519, 2-520, 2-521, 2-522, 2-523, 2-524, 2-525, 2-526, 2-527, 2-529, 2-530, 2-531, 2-532, 2-533, 2-534, 2-536, 2-537, 2-539, 2-540, 2-541, 2-543, 2-544, 2-545, 2-546, 2-547, 2-548, 2-549, 2-550, 2-552, 2-554, 2-555, 4-1, 4-3, 4-5, 5-1, 5-2, 5-4, 5-21, 5-22, 5-23, 5-24, 5-25, 5-26, 5-27, 5-28, 5-50, 5-51, 6-1, 6-2, 6-5, 6-7, 6-8 -10, 6-11, 6-12, 6-13, 6-14, 6-18, 6-19, 6-21, 6-22, 6-23, 6-31, 6-37, 6-38, 6-41, 6-45, 6-47, 6-48, 6-49, 6-51, 6-52, 6-64, 6-65, 6-66, 6-67, 6-71, 6-73, 6-74, 6-75, 6-76, 6-78, 6-79, 6-80, 6-81, 6-82, 6-83, 6-84, 6-85, 6-86, 6-89, 6-91, 6-95, 6-102, 6-103, 6-104, 6 6-105, 6-106, 6-107, 6-108, 6-109, 6-110, 6-111, 6-112, 6-113, 6-114, 6-115, 6-116, 6-117, 6-119, 6-120, 6-121, 6-123, 6-124, 6-125, 6-128, 6-129, 6-131, 6-132, 6-133, 6-134, 6-135, 6-136, 6-139, 8-1, 8-2, 8-4, 8-6, 8-8, 8-10, 8-11, and 8-12 showed a mortality rate of over 90% at a concentration of 200 ppm. Furthermore, the aforementioned compounds No. 1-226, 1-227, 1-231, 1-232, 2-39, 2-189, 2-281, 2-412, 2-440, 2-499, 2-535, 2-538, 6-40, 6-98, 6-122,6-126 and 8-7 showed a kill rate of over 90% at a concentration of 50ppm.

[0392] Test Example 2 Test on the effect of peach aphids 5 adult peach aphids were placed on radish leaves inserted into a test tube with water. After one day, the adults were removed, and the number of larvae parasitizing on the radish leaves was counted as the number of test insects, and the leaves were immersed in a solution prepared in such a way that the concentration of the test compound became 200ppm or 50ppm. After the solution was air-dried, it was placed in a constant temperature room with lighting at 25°C. After 5 days of treatment, the life and death of peach aphids was determined, and the death rate (%) was calculated by the following calculation formula. In addition, detached insects and abnormal insects were regarded as dead insects. [Calculation formula] Death rate (%) = (number of dead insects / number of test insects) × 100 As a result, the aforementioned compounds No. 1-1, 1-2, 1-3, 1-4, 1-5, 1-7, 1-8, 1-10, 1-11, 1-13, 1-45, 1-47, 1-49, 1-51, 1-52, 1-53, 1-57, 1-58, 1-60, 1-61, 1-63, 1-64, 1-65, 1-66, 1-67, 1-68, 1-69, 1-70, 1-71, 1-73, 1-74, 1-76, 1-77, 1-100, 1-101, 1-103, 1-105, 1-1 06, 1-107, 1-109, 1-110, 1-111, 1-113, 1-116, 1-128, 1-129, 1-132, 1-133, 1-135, 1-136, 1-139, 1-140, 1-144, 1-146, 1-148, 1-149, 1-151, 1-152, 1-156, 1-157, 1-158, 1-160, 1-161, 1-162, 1-163, 1-164, 1-165, 1-166, 1-167, 1-168, 1- 170, 1-175, 1-176, 1-178, 1-180, 1-183, 1-184, 1-191, 1-192, 1-195, 1-196, 1-197, 1-198, 1-201, 1-205, 1-206, 1-207, 1-208, 1-209, 1-210, 1-212, 1-213, 1-214, 1-215, 1-217, 1-218, 1-219, 1-220, 1-221, 1-222, 1-223, 1-225, 1-226, 1 -231, 1-233, 1-236, 1-237, 1-239, 1-240, 1-241, 1-242, 1-243, 1-245, 1-250, 1-251, 1-252, 1-253, 1-256, 1-257, 1-258, 1-260, 1-261, 1-262, 1-267, 1-273, 1-274, 1-275, 1-276, 1-277, 1-278, 1-282, 1-283, 1-284, 1-285, 1-286, 1-289,1-292、1-293、1-294、1-296、1-297、1-298、1-299、1-300、1-301、2-1、2-2、2-6、2-12、2-13、2-14、2-15、2-18、2-19、2-20、2-23、2-24、2-25、2-26、2-28、2-29、2-32、2-36、2-37、2-41、2-42、2-43、2-44、2-45、2-46、2-50、2-54、2-57、2-58、2-65、2-66、2-67、2-75、2-81、2-82、2-83、2-85、2-87、2-88、2-89、2-91、2-92、2-93、2-94、2-96、2-97、2-98、2-99、2-100、2-101、2-102、2-103、2-104、2-105、2-106、2-107、2-111、2-112、2-115、2-116、2-119、2-120、2-121、2-122、2-123、2-126、2-127、2-128、2-129、2-130、2-131、2-133、2-140、2-143、2-144、2-147、2-149、2-151、2-153、2-167、2-168、2-169、2-171、2-172、2-173、2-175、2-177、2-178、2-179、2-180、2-181、2-182、2-183、2-184、2-185、2-186、2-190、2-191、2-192、2-195、2-197、2-198、2-206、2-208、2-209、2-211、2-215、2-218、2-222、2-224、2-234、2-235、2-236、2-237、2-238、2-239、2-240、2-241、2-243、2-262、2-263、2-266、2-270、2-271、2-274、2-277、2-278、2-279、2-283、2-284、2-285、2-286、2-287、2-288、2-291、2-292、2-293、2-295、2-296、2-297、2-299、2-300、2-301、2-302、2-303、2-304、2-309、2-310、2-311、2-313、2-314、2-317、2-318、2-319、2-323、2-324、2-325、2-326、2-328、2-329、2-336、2-338、2-342、2-345、2-347、2-348、2-353、2-356、2-359、2-360、2-363、2-364、2-365、2-366、2-367、2-368、2-369、2-370、2-373、2-382、2-383、2-384、2-385、2-387、2-388、2-390、2-393、2-394、2-395、2-396、2-398、2-399、2-401、2-403、2-407、2-409、2-413、2-414、2-415、2-422、2-423、2-424、2-426、2-428、2-429、2-430、2-431、2-432、2-433、2-434、2-435、2-436、2-437、2-438、2-439、2-441、2-444、2-446、2-447、2-448、2-449、2-450、2-452、2-453、2-454、2-456、2-457、2-458、2-459、2-460、2-461、2-462、2-463、2-464、2-465、2-466、2-467、2-468、2-469、2-470、2-471、2-472、2-474、2-475、2-476、2-477、2-478、2-479、2-480、2-482、2-483、2-484、2-485、2-490、2-493、2-495、2-496、2-497、2-498、2-500、2-501、2-502、2-503、2-504、2-505、2-506、2-507、2-508、2-509、2-510、2-511、2-512、2-513、2-515、2-516、2-517、2-519、2-520、2-521、2-522、2-523、2-524、2-525、2-526、2-527、2-530、2-531、2-532、2-533、2-534、2-536、2-537、2-539、2-540、2-541、2-543、2-544、2-545、2-546、2-547、2-548、2-549、2-550、2-552、2-554、2-555、4-1、4-3、4-5、5-1、5-2、5-4、5-21、5-22、5-23、5-24、5-25、5-26、5-27、5-28、5-50、5-51、6-1、6-2、6-5、6-7、6-11、6-12、6-13、6-14、6-18、6-19、6-21、6-22、6-23、6-30、6-31、6-33、6-38、6-41、6-45, 6-47, 6-48, 6-49, 6-51, 6-52, 6-64, 6-65, 6-66, 6-67, 6-73, 6-74, 6-75, 6-76, 6-78, 6-79, 6-80, 6-81, 6-82, 6-83, 6-84, 6-85, 6-89, 6-94, 6-95, 6-102, 6-103, 6-104, 6-105, 6-106, 6-107, 6-108, 6-109, 6-111, 6-11 2. 6-113, 6-114, 6-115, 6-116, 6-117, 6-118, 6-119, 6-120, 6-121, 6-123, 6-124, 6-125, 6-128, 6-129, 6-131, 6-132, 6-133, 6-134, 6-135, 6-136, 6-139, 8-1, 8-2, 8-4, 8-6, 8-8, 8-10, 8-11 and 8-12 showed a mortality rate of more than 90% at a concentration of 200 ppm. Furthermore, the aforementioned compounds No. 2-39, 2-189, 2-281, 2-412, 2-440, 2-499, 2-535, 2-538, 6-10, 6-40, 6-98, 6-122, and 6-126 showed an insecticide rate of more than 90% at a concentration of 50 ppm.

[0393] Test Example 3 Effect test on spider mites Two-spotted. Mung bean leaves on which about 20 adult spider mites were previously released were immersed in a solution prepared with a test compound concentration of 800ppm, 200ppm or 50ppm. After the solution was air-dried, it was placed in a constant temperature room with lighting at 25°C. Three days after the treatment, the life and death of the adult spider mites was determined, and the mortality rate (%) was calculated using the following calculation formula. Insects that had fallen off or had abnormalities were considered dead. [Calculation formula] Adult killing rate (%) = (number of dead insects / number of released insects) × 100 As a result, the aforementioned compounds No. 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-12, 1-27, 1-52, 1-53, 1-54, 1-60, 1-63, 1-65, 1-69, 1-77, 1-96, 1-100, 1-101, 1-104, 1-105, 1-106, 1-107, 1-109, 1-110, 1-111, 1-113, 1-115, 1-128, 1-129, 1-131, 1-132, 1-133, 1-136, 1 -138, 1-140, 1-147, 1-148, 1-149, 1-151, 1-155, 1-156, 1-164, 1-166, 1-167, 1-170, 1-171, 1-175, 1-178, 1-186, 1-189, 1-190, 1-191, 1-192, 1-198, 1-205, 1-206, 1-207, 1-208, 1-209, 1-212, 1-213, 1-214, 1-215, 1-216, 1-217, 1-220, 1-221 , 1-222, 1-223, 1-224, 1-225, 1-226, 1-232, 1-236, 1-237, 1-239, 1-240, 1-241, 1-242, 1-251, 1-252, 1-253, 1-257, 1-258, 1-259, 1-260, 1-262, 1-264, 1-270, 1-273, 1-274, 1-275, 1-276, 1-277, 1-278, 1-283, 1-284, 1-285, 1-286, 1-289, 2-3 , 2-4, 2-8, 2-9, 2-11, 2-12, 2-13, 2-14, 2-15, 2-18, 2-19, 2-23, 2-24, 2-25, 2-26, 2-27, 2-29, 2-32, 2-36, 2-37, 2-38, 2-40, 2-41, 2-46, 2-48, 2-49, 2-50, 2-51, 2-52, 2-54, 2-55, 2-56, 2-57, 2-59, 2-60, 2-63, 2-67, 2-68, 2-69, 2-70, 2-72, 2-74,2-75, 2-76, 2-78, 2-79, 2-80, 2-81, 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91, 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-107, 2-109 , 2-110, 2-111, 2-112, 2-113, 2-114, 2-115, 2-116, 2-117, 2-119, 2-120, 2-121, 2-122, 2-123, 2-126, 2-127, 2-137, 2-139, 2-167, 2-168, 2-234, 2-263, 2-266, 2-270, 2-274, 2-279, 2-283, 2-284, 2-292 , 2-293, 2-294, 2-295, 2-296, 2-335, 2-336, 2-338, 2-340, 2-342, 2-345, 2-347, 2-348, 2-349, 2-352, 2-353, 2-356, 2-357, 2-358, 2-359, 2-360, 2-361, 2-362, 2-363, 2-364, 2-365, 2-366, 2-367, 2-368 8. 2-370, 2-371, 2-372, 2-377, 2-378, 2-379, 2-380, 2-383, 2-384, 2-386, 2-389, 2-424, 2-426, 2-428, 2-429, 2-432, 2-453, 2-455, 2-456, 2-457, 2-462, 2-463, 2-464, and 2-469 showed an adult insecticide rate of over 80% at a concentration of 800 ppm. Furthermore, the aforementioned compounds Nos. 1-219, 1-292, 1-293, 1-297, 2-6, 2-20, 2-42, 2-71, 2-73, 2-106, 2-128, 2-130, 2-131, 2-133, 2-136, 2-140, 2-143, 2-144, 2-149, 2-151, 2-169, 2-171, 2-172, 2-173, 2-175, 2-177, 2-178 8, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-192, 2-195, 2-197, 2-198, 2-218, 2-222, 2-224, 2-235, 2-236, 2-237, 2-238, 2-239, 2-241, 2-243, 2-262, 2-271, 2-277, 2-278, 2-285,2-286, 2-287, 2-288, 2-291, 2-297, 2-298, 2-299, 2-300, 2-301, 2-302, 2-303, 2-304, 2-309, 2-310, 2-311, 2-313, 2-314, 2-317, 2-318, 2-319, 2-323, 2-324, 2-325, 2-326, 2-328, 2-329, 2-369, 2-373, 2-387, 2-388, 2-390, 2-393, 2-394, 2-395, 2-396, 2-398, 2-399, 2-403 , 2-404, 2-409, 2-413, 2-414, 2-415, 2-430, 2-431, 2-433, 2-434, 2-435, 2-436, 2-437, 2-438, 2-439, 2-441, 2-446, 2-448, 2-449, 2-450, 2-451, 2-452, 2-454, 2-458, 2-459, 2-460, 2-461, 2-465, 2-466, 2-467, 2-468, 2-470, 2-472, 2-473, 2-474, 2-475, 2-476, 2-477, 2-478 8, 2-480, 2-481, 2-482, 2-483, 2-484, 2-485, 2-493, 2-496, 2-497, 2-498, 2-502, 2-503, 2-504, 2-505, 2-506, 2-507, 2-509, 2-512, 2-513, 2-516, 2-521, 2-525, 2-526, 2-533, 2-534, 2-536, 2-537, 2-540, 2-541, 2-543, 2-544, 2-545, 2-546, 2-547, 2-548, 2-549, 2-554, 2-555 4. 6-5, 6-7, 6-10, 6-12, 6-13, 6-14, 6-18, 6-21, 6-22, 6-23, 6-41, 6-45, 6-47, 6-49, 6-51, 6-64, 6-67, 6-74, 6-75, 6-80, 6-83, 6-84, 6-89, 6-102, 6-104, 6-105, 6-106, 6-107, 6-108, 6-109, 6-111, 6-113, 6-116, 6-119, 6-120, 6-125, 6-129, and 6-134 showed an adult insecticide rate of over 80% at a concentration of 200 ppm. Furthermore, the aforementioned compounds No. 2-281 and 2-447 showed an adult insecticide rate of over 80% at a concentration of 50 ppm.

[0394] Next, a comparative test comparing the effects of the compounds of the present invention and comparative compounds that do not have the diaryl pyridazinone structure specified in the present invention is described.

[0395] Comparative Test Example 1: Rice seedlings were immersed in a solution prepared to a concentration of 200ppm or 50ppm of the test compound. After the solution was air-dried, the roots were wrapped with moistened cotton wool and placed in a test tube. Approximately 10 2nd to 3rd instar larvae of brown planthoppers were released into the tube, the tube opening was covered with gauze, and the tube was placed in a constant temperature room with lighting at 25°C. Five days after the treatment, the life or death of the brown planthoppers was determined, and the mortality rate (%) was calculated using the following calculation formula. [Calculation formula] Mortality rate (%) = (number of dead insects / number of released insects) × 100. Compound No. 2-12 was used as the compound of the present invention as the test compound, and the following comparative compounds (A) and (B) were used as the comparative compounds.

[0396]

[0397] The comparison results are shown in Table 10 below.

[0398]

[0399] Comparative Test Example 2 Five adult peach aphids were placed on radish leaves placed in a test tube with water. One day later, the adults were removed and the number of larvae parasitizing the radish leaves was counted as the number of test insects. The leaves were then immersed in a solution prepared to a concentration of 200 ppm or 50 ppm of the test compound. After air-drying the solution, the leaves were placed in a constant temperature room with lighting at 25°C. Five days after treatment, the life or death of the peach aphids was determined, and the mortality rate (%) was calculated using the following formula. Insects that had detached or abnormally appeared were considered dead. [Calculation formula] Mortality rate (%) = (number of dead insects / number of test insects) × 100 The test compound was the same as that in Comparative Test Example 1.

[0400] The comparison results are shown in Table 11 below.

[0401]

[0402] Next, a preparation example is described.

[0403] Formulation Example 1 (1) 20 parts by weight of the compound of the present invention (2) 70 parts by weight of clay (3) 5 parts by weight of white carbon (4) 3 parts by weight of sodium polycarboxylate (5) 2 parts by weight of sodium alkylnaphthalenesulfonate The above are uniformly mixed to form a hydrating agent.

[0404] Formulation Example 2 (1) 5 parts by weight of the compound of the present invention (2) 60 parts by weight of talc (3) 34.5 parts by weight of calcium carbonate (4) 0.5 parts by weight of liquid paraffin The above are uniformly mixed to form a powder.

[0405] Formulation Example 3 (1) 20 parts by weight of the compound of the present invention (2) 20 parts by weight of N,N-dimethylacetamide (3) 10 parts by weight of polyoxyethylene tristyrylphenyl ether (4) 2 parts by weight of calcium dodecylbenzenesulfonate (5) 48 parts by weight of xylene The above are uniformly mixed and dissolved to form an emulsion.

[0406] Formulation Example 4 (1) 68 parts by weight of clay (2) 2 parts by weight of sodium lignin sulfonate (3) 5 parts by weight of polyoxyethylene alkylaryl sulfate (4) 25 parts by weight of white carbon A mixture of the above ingredients and the compound of the present invention are mixed in a weight ratio of 4:1 as a hydrating agent.

[0407] Preparation Example 5 (1) 50 parts by weight of the compound of the present invention (2) 2 parts by weight of sodium alkylnaphthalenesulfonate formaldehyde condensate (3) 0.2 parts by weight of silicone oil (4) 47.8 parts by weight of water are uniformly mixed, and (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are further added to the crushed stock solution and uniformly mixed, granulated, and dried to prepare a granular hydrating agent.

[0408] Formulation Example 6 (1) 5 parts by weight of the compound of the present invention (2) 1 part by weight of polyoxyethylene octylphenyl ether (3) 0.1 part by weight of polyoxyethylene alkyl ether phosphate (4) 93.9 parts by weight of granular calcium carbonate (1) to (3) are uniformly mixed in advance, diluted with an appropriate amount of acetone, and blown onto (4). The acetone is removed to prepare granules.

[0409] Formulation Example 7 (1) 2.5 parts by weight of the compound of the present invention (2) 2.5 parts by weight of N,N-dimethylacetamide (3) 95.0 parts by weight of soybean oil are uniformly mixed and dissolved to form an ultra low volume formulation.

[0410] Formulation Example 8 (1) 10 parts by weight of the compound of the present invention (2) 80 parts by weight of diethylene glycol monoethyl ether (3) 10 parts by weight of polyoxyethylene alkyl ether The above ingredients are uniformly mixed to form a liquid.

[0411] The entire contents of the specification, patent application scope and abstract of Japanese Patent Application No. 2022-056258 applied for on March 30, 2022 are cited here and incorporated as a disclosure of the specification of the present invention.

Claims

1. A pyridazinone compound or a salt thereof represented by formula (I), wherein Q is Q1, Q2, Q3 or Q4; X is CH, C(RA) or N; Y and RA are halogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfinyl, haloalkylthio, haloalkylsulfinyl, hydroxyl, cyano, nitro, -SF5, -NRBRC, -C(=O)RD or -C(=O)NRERF; Z is alkyl, alkenyl, alkynyl, alkoxyalkyl, cycloalkylalkyl or haloalkyl; R1, R2, R3 and R 4 represents halogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxy, cycloalkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfinyl, haloalkylthio, haloalkylsulfinyl, hydroxyl, cyano, nitro, -NR GR H, -C(=O)RI, -C(=O)NR JR K, -C(=NOR L)RM, dimethoxymethyl, 1,3-dioxane-2-yl or 1,3-dioxolane-2-yl; RB, RC, RE, RF, RG, RH, RJ and RK represent hydrogen atoms, alkyl or haloalkyl; RD and RI represent hydrogen atoms, hydroxyl, alkyl, haloalkyl or alkoxy; RL and RM represent hydrogen atoms or alkyl; n is an integer from 0 to 4; a is an integer from 0 to 3; b, c and d are 0, 1 or 2 respectively.

2. The pyridazinone compounds or salts thereof as claimed in claim 1, wherein, Y and RA are respectively halogen, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C6)cycloalkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4) alkylthio, (C1-C4) alkylsulfinyl, (C1-C4) alkylsulfinyl, (C1-C4) haloalkylthio, (C1-C4) haloalkylsulfinyl, (C1-C4) haloalkylsulfinyl, hydroxyl, cyano, nitro, -SF5, -NRBRC, -C(=O)RD or -C(=O)NRERF; Z is (C1-C5)alkyl, (C2-C6)alkyl, (C3-C6)cycloalkyl, (C1-C4)haloalkyl, (C2-C6)cyclo ... 4) Alkenyl, (C2-C4) alkynyl, (C3-C6) cycloalkyl, (C1-C4) alkoxy (C1-C4) alkyl, (C3-C6) cycloalkyl (C1-C4) alkyl, or (C1-C4) haloalkyl; R1, R2, R3, and R4 are respectively halogen, (C1-C4) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, (C3-C6) cycloalkyl, (C1-C4) haloalkyl, (C1-C4) alkoxy, (C3-C6) cycloalkoxy, (C1-C4) haloalkoxy, (C1-C4) alkylthio, (C1-C4) alkylsulfinyl ... 4) Alkylsulfonyl, (C1-C4) haloalkylthio, (C1-C4) haloalkylsulfinyl, (C1-C4) haloalkylsulfonyl, hydroxyl, cyano, nitro, -NR GR H, -C(=O)RI, -C(=O)NR JR k, -C(=NOR L)RM, dimethoxymethyl, 1,3-dioxane-2-yl or 1,3-dioxolane-2-yl; RB, RC, RE, RF, RG, RH, RJ and RK are hydrogen atoms, (C1-C4) alkyl or (C1-C4) haloalkyl, respectively; RD and RI are hydrogen atoms, hydroxyl, (C1-C4) alkyl, (C1-C4) haloalkyl or (C1-C4) alkoxy, respectively; RL and RM are hydrogen atoms or (C1-C4) alkyl, respectively.

3. The pyridazinone compounds or salts thereof as claimed in claim 1, wherein, Y and RA are respectively halogen, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C6)cycloalkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylsulfonyl, (C1-C4)haloalkylthio, (C1-C4)haloalkylsulfinyl, (C1-C4)haloalkylsulfonyl, cyano, nitro, or -C(=O)RD; Z is (C1-C5)alkyl, (C3-C6)cycloalkyl, (C1-C4)alkoxy(C1-C4)alkyl, or (C1-C4)haloalkyl; R1, R2, R3, and R 4 represents halogen, (C1-C4)alkyl, (C2-C4)alkynyl, (C3-C6)cycloalkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4) alkylthio, (C1-C4)alkylsulfinyl, (C1-C4)alkylsulfonyl, cyano, nitro, -NRGRH, -C(=O)RI, -C(=NORL)RM, dimethoxymethyl, 1,3-dioxane-2-yl, or 1,3-dioxolane-2-yl; RG and RH represent hydrogen atoms or (C1-C4)alkyl; RD and RI represent hydrogen atoms, (C1-C4)alkyl, or (C1-C4)alkoxy; RL and RM represent hydrogen atoms or (C1-C4)alkyl. 1-C 4)alkyl.

4. The pyridazinone compounds or salts thereof as claimed in claim 1, wherein, Q can be either Q1 or Q3.

5. A pyridazinone compound or a salt thereof, as claimed in claim 1, wherein, X is CH or C(RA).

6. The pyridazinone compounds or salts thereof as claimed in claim 1, wherein, X is N.

7. The pyridazinone compounds or salts thereof as claimed in claim 1, wherein, When X is CH, n is an integer from 1 to 3; when X is C(RA) or N, n is 1 or 2.

8. A pyridazinone compound or a salt thereof, as claimed in claim 1, wherein, a, b, c, and d are 1 or 2 respectively.

9. A pest control agent comprising, as an active ingredient, any one of claims 1 to 8, a compound or a salt thereof.

10. An agricultural or horticultural insecticide, acaricide, nematicide, or soil pest control agent, comprising a compound or salt thereof as an active ingredient, as claimed in any one of claims 1 to 8.

11. A method for controlling pests, comprising applying an effective amount of a compound or a salt thereof as claimed in any one of claims 1 to 8.