Pyridazinone compound or salt thereof, and pest control agent containing same

Abstract

A number of pest control agents have been used over the years, but a considerable number of such pest control agents have various problems such as insufficient efficacy and limitation on the use thereof due to pests, etc., gaining resistance thereto. Therefore, there is a demand for development of a new pest control agent with few of such shortcomings. The present invention pertains to: a pyridazinone compound represented by formula (I) [in the formula, each symbol is as described in the description] or a salt thereof; a pest control agent containing the compound; and a method for controlling pests by applying the compound.

Description

Pyridazinone compounds or salts thereof and pest control agents containing them

[0001] The present invention relates to a novel pyridazinone compound or a salt thereof and a pest control agent containing the compound or salt as an active ingredient.

[0002] Patent Document 1 describes a 4-(heterocyclyl)pyridazinone compound. This compound has an alkyl, cycloalkyl, etc. at the 2-position of the pyridazinone ring, and does not have an aromatic ring at the same position as the compound represented by formula (I) described below, and the two compounds have different chemical structures. Patent Documents 2 and 3 describe pyridazinone compounds. This compound has an alkyl, cycloalkyl, tetrahydropyranyl, etc. at the 2-position of the pyridazinone ring, and does not have an aromatic ring at the same position as the compound represented by formula (I) described below, and the two compounds have different chemical structures. Patent Document 4 describes a pyridazinone compound. This compound has an A-R group at the 4-position of the pyridazinone ring. ３ (A is NR ４ and R ４ is C １ ~C ６ or R ３ and may form a 5- or 6-membered ring together with

[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 agent for proliferative diseases. Patent Document 8 describes a pyridazinone compound and a P2X7 receptor inhibitor. However, Patent Documents 5 to 8 do not specifically disclose compounds in which the 2-position of the pyridazinone ring is an aromatic ring and the 4-position of the pyridazinone ring is a pyrazole or triazole, such as the compound represented by formula (I) below, and furthermore, there is no disclosure regarding the control of agricultural and horticultural pests or animal parasitic organisms.

[0004] Patent Document 9, which was published after the priority date of the present application, describes a pyridazinone compound. The compound has an OH group at the 5-position of the pyridazinone ring, and does not disclose a compound in which the OH group is modified, such as the compound represented by formula (I) described below.

[0005] International Publication No. WO 2011 / 045271 International Publication No. WO 2009 / 086041 JP 2012-56903 A JP 63-185966 A International Publication No. WO 2015 / 143164 International Publication No. WO 2008 / 103277 International Publication No. WO 2008 / 080056 International Publication No. WO 2010 / 126104 International Publication No. WO 2023 / 189602

[0006] Although many pesticides have been used for many years, many of them have various problems, such as insufficient efficacy and limitations on their use due to pest resistance. Therefore, there is a need for the development of a new pesticide that has fewer of these drawbacks. The object of the present invention is to provide a compound that is highly active against pests, a pesticide containing the compound, and a method for controlling pests by applying the compound.

[0007] The present inventors have conducted extensive research on pyridazinone compounds in order to find a more effective pesticide. As a result, they have found that a novel diarylpyridazinone compound represented by the formula (I) below, which has 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 via its nitrogen atom, or a salt thereof, has a pesticidal effect, and have completed the present invention. That is, the present invention relates to a compound represented by the formula (I):

[0008] (Wherein, Q is Q １ , Q ２ , Q ３ or Q ４ :

[0009] (In each formula, * indicates the bonding position); X is CH, C(R Ａ ) or N; Y and R Ａeach represents a halogen, an alkyl, an alkenyl, an alkynyl, a cycloalkyl, a haloalkyl, an alkoxy, a haloalkoxy, an alkylthio, an alkylsulfinyl, an alkylsulfonyl, a cyano, or —C(═O)R Ｂ Z is alkyl, cycloalkyl, alkoxyalkyl, cycloalkylalkyl or haloalkyl; R １ , R ２ , R ３ and R ４ are each halogen, alkyl, cycloalkyl, haloalkyl, alkoxy, cycloalkyloxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, cyano, nitro, aldehyde, -CH(=NOR Ｃ ), 1,3-dioxan-2-yl or 1,3-dioxolan-2-yl; R Ｂ is a hydrogen atom or alkyl; R Ｃ is alkyl; n is an integer from 0 to 4; a is an integer from 0 to 3; b, c and d are each 0, 1 or 2; G is R Ｄ alkyl optionally substituted with -C(=O)E or alkylsulfonyl; R Ｄ is alkoxy, cyano, alkoxycarbonyl or alkoxycarbonyloxy; E is alkyl, alkenyl, cycloalkyl, heterocycloalkyl, haloalkyl, haloalkenyl, dialkylamino, N-alkoxy-N-alkylamino, V Ａ phenyl optionally substituted with V Ａ pyridyl, cycloalkylalkyl, heterocycloalkylalkyl, alkoxyalkyl, alkylthioalkyl, optionally substituted with V Ａ phenylalkyl optionally substituted with V Ａ phenyloxyalkyl optionally substituted with V Ａ phenylalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, heterocycloalkyloxy, haloalkoxy, alkoxyalkoxy, optionally substituted with V Ａ phenyloxy optionally substituted with VＡ naphthyloxy, cycloalkylalkoxy, heterocycloalkylalkoxy, optionally substituted with V Ｂ phenylalkoxy, alkylthio or 2-imidazolidinone optionally substituted with; V Ａ is a halogen; Ｂ and R is halogen or alkyl, or a salt thereof.

[0010] The present invention also relates to a pesticide containing the pyridazinone compound represented by formula (I) or a salt thereof as an active ingredient, and to a method for controlling undesirable organisms by applying an effective pesticidal amount of the compound or a salt thereof to undesirable organisms or to a place where they grow.

[0011] The pyridazinone compound represented by the formula (I) or a salt thereof exerts a pest control effect on pests.

[0012] The halogen atom or halogen atom as a substituent in the formula (I) may be a fluorine, chlorine, bromine, or iodine atom. The number of halogen atoms as a substituent may be one or more, and when there are two or more, the halogen atoms may be the same or different. The substitution position of the halogen atom may be any position.

[0013] The alkyl or alkyl moiety in the formula (I) may be, for example, a straight-chain or branched alkyl group having 1 to 8 carbon atoms (C), such as methyl, ethyl, normal propyl, isopropyl, normal butyl, isobutyl, secondary butyl, tertiary butyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 2,2,3-trimethylbutyl, normal pentyl, isopentyl, neopentyl, 2-methylpentyl, 3-methylpentyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 3,3-dimethylpentyl, 3-ethylpentyl, normal hexyl, 2-methylhexyl, 3-methylhexyl, normal heptyl, or normal octyl. １ -C ８ ) groups are exemplified.

[0014] The alkoxy or alkoxy moiety in the formula (I) includes, for example, straight-chain or branched alkoxy having 1 to 7 carbon atoms (C), such as methoxy, ethoxy, propoxy, isopropoxy, normal butoxy, isobutoxy, secondary butoxy, tertiary butoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, normal pentyloxy, isopentyloxy, neopentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, normal hexyloxy, or normal heptyloxy. １ -C ７ ) groups are exemplified.

[0015] The alkenyl or alkenyl moiety in the formula (I) may be, for example, a straight-chain or branched alkenyl having 2 to 8 carbon atoms (C) having at least one double bond at any position, such as vinyl, 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, 3-butenyl, 1-pentenyl, 2-pentenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-hexenyl, 2,3-dimethyl-2-butenyl, 1-heptenyl, or 1-octenyl. ２ -C ８ ) groups are exemplified.

[0016] The alkynyl or alkynyl moiety in the formula (I) may be, for example, a straight-chain or branched alkynyl having 2 to 7 carbon atoms (C) having at least one triple bond at any position, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, or 1-heptynyl. ２ -C ７ ) groups are exemplified.

[0017] The cycloalkyl or cycloalkyl moiety in the formula (I) is, for example, a cycloalkyl having 3 to 6 carbon atoms (C ), such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. ３ -C ６The cycloalkyl or the ring in the cycloalkyl moiety may be substituted with an alkyl group at any position on the ring, and examples of such cycloalkyl or cycloalkyl moiety include groups having 3 to 6 carbon atoms (C), such as 1-methylcyclopropyl, 2-methylcyclopropyl, 1,2-dimethylcyclopropyl, 2,2-dimethylcyclopropyl, 1-methylcyclobutyl, and 1-methylcyclopentyl. ３ -C ６ ) groups (in this case, the number of carbon atoms includes the number of carbon atoms of the alkyl group resulting from substitution).

[0018] Examples of the heterocycloalkyl or heterocycloalkyl moiety in formula (I) include oxiranyl, thiiranyl, aziridinyl, oxetanyl, thietanyl, azetidinyl, dihydrofuryl, tetrahydrofuryl, dihydrothiophenyl, tetrahydrothiophenyl, pyrrolinyl, pyrrolidinyl, dioxolyl, dioxolanyl, dithiolanyl, oxathiolanyl, imidazolinyl, imidazolidinyl, pyrazolinyl, pyrazolidinyl, oxazolinyl, and oxazolidinyl. and 3- to 6-membered groups containing, in addition to carbon atoms, one or more atoms selected from oxygen atoms, nitrogen atoms, and sulfur atoms, such as tetrahydropyranyl, isoxazolinyl, isoxazolidinyl, thiazolinyl, thiazolidinyl, isothiazolinyl, isothiazolidinyl, tetrahydropyranyl, dihydropyranyl, tetrahydrothiopyranyl, dihydrothiopyranyl, dioxanyl, piperidinyl, piperazinyl, tetrahydropyrazinyl, tetrahydropyridazinyl, and morpholinyl.

[0019] The pyridyl in the formula (I) may be any of 2-pyridyl, 3-pyridyl and 4-pyridyl, and the position of the nitrogen atom is not particularly limited.

[0020] In the formula (I), the term "may be substituted" means that it is substituted or unsubstituted.

[0021] In the formula (I), when n is an integer of 2 or more, each substituent Y may be the same or different. Similarly, when a is an integer of 2 or more, each substituent R １may be the same or different. Similarly, when b, c, or d is 2, R ２ , R ３ and R ４ The substituents may be the same or different.

[0022] In the formula (I), Q is Q １ ~Q ４ Therefore, the compound of formula (I) is specifically represented by the following formulas (i) to (iv).

[0023]

[0024] The compound of formula (i) is Q １ Depending on the number and positions of the substituents in the formula (ia), the compounds include compounds of the following formula (ih).

[0025]

[0026] Similarly, the compound of formula (ii) may be ２ Depending on the number and positions of the substituents in the formula (ii-a) to (ii-c), the compounds include compounds of the following formula (ii-a) to formula (ii-c).

[0027]

[0028] Similarly, the compound of formula (iii) may be ３ Depending on the number and positions of the substituents in the formula (iii-a) to (iii-d), the compounds include compounds of the following formula (iii-a) to formula (iii-d).

[0029]

[0030] Similarly, the compound of formula (iv) may be ４ Depending on the number and positions of the substituents in the formula (iv-a) to (iv-d), the compounds include compounds of the following formula (iv-a) to formula (iv-d).

[0031]

[0032] The symbols in the compounds of formulas (i) to (iv), formulas (ia) to (i-h), formulas (ii-a) to (ii-c), formulas (iii-a) to (iii-d), and formulas (iv-a) to (iv-d) have the same meanings as those in formula (I). Further, the description of the compound of formula (I) in this specification also includes the description of the compounds of the formulas included in formula (I).

[0033] In formula (I), Q is Q １ or Q ３ is preferred, that is, the compounds represented by the above formula (i) or formula (iii) are preferred. Furthermore, the compounds represented by formula (i) or formula (iii) are preferably compounds represented by formula (ic), formula (id), formula (ig) or formula (iii-c).

[0034] The salt of the compound of formula (I) includes any salt acceptable in the art, for example, inorganic acid salts such as hydrochloride, perchlorate, sulfate, and nitrate; and organic acid salts such as acetate and methanesulfonate.

[0035] The compound of formula (I) or a salt thereof may have isomers such as diastereoisomers and optical isomers, and the present invention includes both each isomer and a mixture of isomers. In this specification, unless otherwise specified, isomers are described as a mixture. The present invention also includes various isomers other than the above-mentioned isomers within the scope of common general knowledge in the technical field. Depending on the type of isomer, the chemical structure may differ from that of general formula (I). However, a person skilled in the art would be able to fully recognize that these chemical structures are isomers of general formula (I), and therefore, they are clearly within the scope of the present invention.

[0036] The compound of formula (I) or a salt thereof (hereinafter also referred to as the compound of the present invention) can be prepared according to the following preparation method or a conventional salt preparation method, but is not limited to these methods. For example, compound (I) of the present invention can also be prepared by applying various substituent conversion reactions known in the art to the substituents on the pyridazinone ring and the pyrazolyl, triazolyl, phenyl, or pyridyl group (e.g., alkylation reaction, haloalkylation reaction, cross-coupling reaction such as Suzuki coupling reaction, Sandmeyer reaction, halogenation reaction, oxidation reaction, reduction reaction, etc.). If necessary, any functional group in the starting material or intermediate may be protected with a protecting group known in the art. These protecting groups can be removed at an appropriate stage in the reaction sequence using methods known in the art. Furthermore, the reaction may be carried out under an inert gas atmosphere such as nitrogen or argon, if necessary. In addition, in the preparation methods described below, isomers such as diastereoisomers and optical isomers may exist, and the following description encompasses both individual isomers and mixtures containing them in any ratio. For example, a chemical structural formula may contain geometric isomers derived from a carbon-nitrogen double bond, and in such cases, the wavy line in the chemical structural formula means that any of the geometric isomers derived from the carbon-nitrogen double bond is included. Furthermore, for example, a compound of formula (II) described below or a salt thereof, which is useful as a precursor of compound (I), may exist as the following tautomers, and the compound of formula (II) described below or a salt thereof includes both each tautomer and a mixture containing these tautomers in any ratio.

[0037]

[0038]

[0023] Production Method [1] The compound of the present invention can be produced by reacting a compound of formula (II) with a compound of formula (III) in the presence of a base. The compound of formula (III) is commercially available or can be produced according to known methods. In this production method, a compound of formula (IV), which is an isomer of the compound of formula (I), may be produced, but the compound of formula (I) can be isolated by ordinary procedures such as purification.

[0039]

[0040] In the formula, L is a halogen atom, and the other symbols are as defined above.

[0041] 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 hexamethyldisilazide, and potassium hexamethyldisilazide; metal alkoxides such as sodium methoxide and potassium tert-butoxide; tertiary amines such as triethylamine, 4-methylmorpholine, and diisopropylethylamine; 1,8-diazabicyclo[5.4.0]-7-undecene, 1,4-diazabicyclo[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 per equivalent of the compound of formula (II).

[0042] The reaction of the production method [1] may be carried out in the presence of a catalyst, if necessary, and examples of the catalyst include sodium iodide, potassium iodide, etc. The catalyst can be used in an amount of 0.005 to 0.8 equivalents per equivalent of the compound of formula (II).

[0043] The reaction of Production Method [1] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and one or more solvents may be appropriately selected or mixed from the following: 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.; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, etc.; and aliphatic hydrocarbons such as pentane, hexane, heptane, octane, cyclohexane, etc.

[0044] The reaction temperature in the production method [1] is about −20° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0045] Intermediate Production Method [1] The compound of formula (II-a) in which X is N among the compounds of formula (II) can be produced by continuously carrying out step 1 in which a compound of formula (V) is reacted with a compound of formula (VI) to obtain a compound of formula (VII), and step 2 in which the compound of formula (VII) is reacted in the presence of a base.

[0046]

[0047] During the ceremony, Z １ is alkyl, and the other symbols are as defined above.

[0048] In step 1 of the intermediate production method [1], a compound of formula (V) is reacted with a compound of formula (VI) in the presence of a base to produce a compound of formula (VII). The compound of formula (VI) is commercially available or can be produced according to known methods.

[0049] 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 (V).

[0050] The reaction of step 1 in the intermediate production method [1] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and one or more solvents selected from the same solvents as those used in the above production method [1] can be used, or they can be used in combination.

[0051] The reaction temperature in step 1 of the intermediate production method [1] is about −20° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0052] In step 2 of the intermediate production method [1], the compound of formula (VII) obtained in step 1 is reacted with a base to produce the compound of formula (II-a).

[0053] Examples of the base include those similar to those in Step 1 above.

[0054] The reaction of step 2 in the intermediate production method [1] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and for example, one or more solvents can be appropriately selected or mixed from the following: 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.; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, etc.; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, cyclohexane, etc.; water; and the like.

[0055] The reaction temperature in step 2 of the intermediate production method [1] is about −20° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0056] Intermediate Production Method [1-1] The compound of formula (V) can be produced by reacting a compound of formula (VIII) with a compound of formula (IX) in the presence of a base. The compound of formula (IX) is commercially available or can be produced according to known methods.

[0057]

[0058] The symbols in the formula are as defined above.

[0059] 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 (VIII).

[0060] The reaction of the intermediate production method [1-1] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and one or more solvents selected from the same solvents as those used in the above production method [1] can be used, or they can be used in combination.

[0061] The reaction temperature in the intermediate production method [1-1] is about 0° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0062] Intermediate Production Method [1-2] 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 the compound of formula (X) in the presence of an acid.

[0063]

[0064] The symbols in the formula are as defined above.

[0065] Examples of the acid include inorganic acids such as hydrochloric acid and organic acids such as acetic acid, formic acid, and trifluoroacetic acid. The acid can be used in an amount of 0.1 to 10 equivalents per equivalent of the compound of formula (X). In some cases, an excess amount of the acid can also be used as a solvent.

[0066] The reaction in the intermediate production process [1-2] can be carried out in the presence of a solvent, if necessary. The solvent may be any solvent inert to the reaction, and is not particularly limited. For example, one or more solvents may be appropriately selected or mixed from the following: 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-pyrrolidone, dimethyl sulfoxide, and sulfolane; 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.

[0067] The reaction temperature in the intermediate production method [1-2] is about 0° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0068] Intermediate Production Method [1-3] The compound of formula (X) can be produced by reacting a compound of formula (XI) with a compound of formula (XII) in the presence of a metal catalyst and a base. The compound of formula (XII) is commercially available or can be produced according to known methods.

[0069]

[0070] In the formula, two R ａ are each independently a hydrogen atom or (C １－C ６ ) alkyl, and two R ａ But (C １－ C ６ ) alkyl, they may be the same or different. ａ Together -CH ２ CH ２ - or -C(CH ３ ) ２ C(CH ３ ) ２ - may be formed, and the other symbols are as described above.

[0071] The metal catalyst may be any catalyst commonly used in cross-coupling reactions. 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. The metal catalyst can be used in an amount of 0.001 to 0.5 equivalents per equivalent of the compound of formula (XI).

[0072] The base can be used by appropriately selecting one or more 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; alkaline earth metal phosphates such as calcium phosphate; etc. The base can be used in an amount of 0.5 to 10 equivalents per equivalent of the compound of formula (XI).

[0073] The reaction in the intermediate production process [1-3] can be carried out in the presence of a solvent, if necessary. The solvent may be any solvent inert to the reaction, and is not particularly limited. For example, one or more solvents may be appropriately selected or mixed from the following: 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-pyrrolidone, dimethyl sulfoxide, and sulfolane; 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.

[0074] The reaction temperature in the intermediate production method [1-3] is about 20° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0075] Intermediate Production Method [1-4] The compound of formula (XI) 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 (XI) can be produced by reacting the compound of formula (XIII) with 3,4-dihydro-2H-pyran in the presence of an acid. The compound of formula (XIII) is commercially available or can be produced according to known methods.

[0076]

[0077] The acid may be, for example, an organic acid such as methanesulfonic acid, trifluoroacetic acid, p-toluenesulfonic acid, pyridinium p-toluenesulfonate, etc. The acid may be used in an amount of 0.1 to 10 equivalents per equivalent of the compound of formula (XIII).

[0078] The reaction in the intermediate production process [1-4] can be carried out in the presence of a solvent, if necessary. The solvent may be any solvent inert to the reaction, and is not particularly limited. For example, one or more solvents may be appropriately selected or mixed from the following: 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-pyrrolidone, dimethyl sulfoxide, and sulfolane; 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.

[0079] The reaction temperature in the intermediate production method [1-4] is about 10° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0080] Intermediate Production Method [2] The compound of the formula (II) can be produced by reacting the compound of the formula (XIV) in the presence of a base.

[0081]

[0082] In the formula, R ｂ (C １－ C ６ ) alkyl, and the other symbols are as defined above.

[0083] 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; alkyllithiums such as normal butyllithium and tertiary butyllithium; metal amides such as lithium diisopropylamide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide; metal alkoxides such as sodium methoxide and potassium tertiary butoxide; 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 (XIV).

[0084] The reaction of the intermediate production method [2] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and one or more solvents may be appropriately selected from the same solvents as those used in the intermediate production method [1-2], or a mixture of two or more solvents may be used.

[0085] The reaction temperature in the intermediate production method [2] is about −20° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0086] Intermediate Production Method [2-1] The compound of formula (XIV) can be produced by reacting a compound of formula (XV) with a compound of formula (XVI), optionally in the presence of an acid. The compound of formula (XVI) is commercially available or can be produced according to a known method, for example, according to the description in known literature (e.g., US2004087569A1 (page 6,

[0092] , page 7,

[0093] , etc.).

[0087]

[0088] The symbols in the formula are as defined above.

[0089] Examples of the acid include inorganic acids such as hydrochloric acid, sulfuric acid, etc., and organic acids such as acetic acid, formic acid, methanesulfonic acid, trifluoroacetic acid, p-toluenesulfonic acid, etc. The acid can be used in an amount of 0.1 to 10 equivalents relative to 1 equivalent of the compound of formula (XV).

[0090] The reaction in the intermediate production process [2-1] can be carried out in the presence of a solvent, if necessary. The solvent may be any solvent inert to the reaction, and is not particularly limited. For example, one or more solvents may be appropriately selected or mixed from the following: 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-pyrrolidone, dimethyl sulfoxide, and sulfolane; 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.

[0091] The reaction temperature in the intermediate production method [2-1] is about −20° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0092] The compound of formula (XV) 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 (XV) can be produced by reacting the compound of formula (XVII) in the presence of an acid.

[0093]

[0094] The symbols in the formula are as defined above.

[0095] Examples of the acid include inorganic acids such as hydrochloric acid and organic acids such as trifluoroacetic acid. The acid can be used in an amount of 0.1 to 10 equivalents per equivalent of the compound of formula (XVII). In some cases, an excess amount of the acid can also be used as a solvent.

[0096] The reaction in the intermediate production method [2-2] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and can be selected from, 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.; esters such as ethyl acetate, ethyl propionate, etc.; and aliphatic hydrocarbons such as pentane, hexane, heptane, octane, cyclohexane, etc., and can be used singly or in combination.

[0097] The reaction temperature in the intermediate production method [2-2] is about 0° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0098] Intermediate Production Method [2-3] The compound of formula (XVII) can be produced by reacting a compound of formula (XVIII) with a compound of formula (XIX) in the presence of a base. The compound of formula (XIX) is commercially available or can be produced by the method of Intermediate Production Method [2-6].

[0099]

[0100] The symbols in the formula are as defined above.

[0101] Examples of the base include those similar to those used in the intermediate production process [2], etc. The base can be used in an amount of 0.5 to 10 equivalents per equivalent of the compound of formula (XVIII).

[0102] The reaction of the intermediate production method [2-3] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and one or more solvents selected from the same solvents as those used in the intermediate production method [1-2] can be used, or they can be used in combination.

[0103] The reaction temperature in the intermediate production method [2-3] is about −20° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0104] Intermediate Production Method [2-4] The compound of formula (XVIII) 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 (XVIII) can be produced by reacting a compound of formula (XX) with, for example, di-tert-butyl dicarbonate ((Boc) ２ O) in the presence of a base, if necessary.

[0105]

[0106] The symbols in the formula are as defined above.

[0107] The reaction in the intermediate production process [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-diazabicyclo[5.4.0]-7-undecene, and 4-(dimethylamino)pyridine. The base can be used in an amount of 0.5 to 10 equivalents per equivalent of the compound of formula (XX).

[0108] The reaction in the intermediate production process [2-4] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and can be selected from, 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-pyrrolidone, dimethyl sulfoxide, and sulfolane; esters such as ethyl acetate and ethyl propionate; and water; or a mixture of two or more solvents can be used.

[0109] The reaction temperature in the intermediate production method [2-4] is about 0° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0110] Intermediate Production Method [2-5] The compound of formula (XX) can be commercially available, or can be prepared by reacting a compound of formula (XXI) with a nitrite such as sodium nitrite in an aqueous solution containing an acid to prepare a diazonium salt of the corresponding formula (XXII), and then reacting the prepared diazonium salt with a reducing agent in an aqueous solution containing an acid. Compounds of formula (XXI) are commercially available or can be prepared according to known methods, for example, as described in known literature (e.g., WO 2021 / 097057 (page 348, Steps 1 to 3 of Intermediate A-7), etc.). In addition, compounds of formula (XXI) can also be prepared by the method of intermediate production method [2-5-1].

[0111]

[0112] In the ceremony, T － are chloride, sulfate, acetate and trifluoroacetate anions, and the other symbols are as previously described.

[0113] The acid may be selected from, for example, inorganic acids such as hydrochloric acid and sulfuric acid; organic acids such as acetic acid and trifluoroacetic acid; or a mixture of two or more acids. The acid is usually used in an amount of 1 equivalent or more relative to 1 equivalent of the compound of formula (XXI), and in some cases in an excess amount that also serves as a solvent.

[0114] The reducing agent includes tin(II) chloride, etc. The reducing agent can be used in an amount of 0.5 to 10 equivalents per equivalent of the compound of formula (XXI).

[0115] The reaction temperature in the intermediate production method [2-5] is about −20° C. to 100° C. The reaction time is about 0.5 to 24 hours.

[0116] Intermediate Production Method [2-5-1] Among the compounds of formula (XXI) in the intermediate production method [2-5], the compound of formula (XXI-a) having alkylthio as Y can be produced, for example, by the following reactions in Step 1 and Step 2.

[0117]

[0118] In the formula, m is an integer of 0 to 3, and Z ２ is a primary alkyl, and the other symbols are as defined above.

[0119] In step 1 of the intermediate production method [2-5-1], the compound of formula (XXXIII) is reacted with ammonium thiocyanate in the presence of an oxidizing agent to produce the compound of formula (XXXIV). The compound of formula (XXXIII) is commercially available or can be produced according to known methods.

[0120] Examples of the oxidizing agent include potassium peroxodisulfate, ammonium peroxodisulfate, etc. The oxidizing agent can be used in an amount of 0.5 to 10 equivalents per equivalent of the compound of formula (XXXIII).

[0121] Step 1 of the intermediate production method [2-5-1] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and can be selected from, 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.; nitriles such as acetonitrile, propionitrile, etc.; alcohols such as methanol, ethanol, isopropyl alcohol, etc.; water; acetic acid, etc., and one or more of these can be appropriately selected or mixed.

[0122] The reaction temperature in step 1 of the intermediate production method [2-5-1] is about 0° C. to 100° C. The reaction time is about 0.5 to 24 hours.

[0123] In step 2 of the intermediate production method [2-5-1], the compound of formula (XXXIV) obtained in step 1 is reacted with a primary alcohol in the presence of a base to produce the compound of formula (XXI-a).

[0124] Examples of primary alcohols include methanol, ethanol, propanol, and butanol.

[0125] Examples of the base include alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, etc.; alkaline earth metal carbonates such as calcium carbonate, barium carbonate, etc.; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, etc.; alkaline earth metal hydroxides such as calcium hydroxide, barium hydroxide, etc.; alkali metal hydrides such as sodium hydride; metal alkoxides such as sodium methoxide, potassium tert-butoxide, etc. The base can be used in an amount of 0.5 to 10 equivalents per equivalent of the compound of formula (XXXIV).

[0126] The reaction temperature in step 2 of the intermediate production method [2-5-1] is about 0° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0127] Intermediate Production Method [2-6] The compound of formula (XIX) can be produced by reacting a compound of formula (XXIII) with a halogenating agent. The compound of formula (XXIII) is commercially available or can be produced by the method of Intermediate Production Method [2-7] or Intermediate Production Method [2-9].

[0128]

[0129] The symbols in the formula are as defined above.

[0130] The halogenating agent is not particularly limited, but examples thereof include thionyl chloride, oxalyl chloride, phosphoryl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus pentachloride, etc. The halogenating agent can be used in an amount of 0.5 to 20 equivalents per equivalent of the compound of formula (XXIII). In some cases, the halogenating agent may be used in an amount of 20 or more equivalents per equivalent of the compound of formula (XXIII).

[0131] The reaction of the intermediate production method [2-6] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and one or more solvents may be appropriately selected from the same solvents as those used in the intermediate production method [1-2], or a mixture of two or more solvents may be used.

[0132] The reaction temperature in the intermediate production method [2-6] is about 0° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0133] Intermediate Production Method [2-7] The compound of the formula (XXIII) can be produced by hydrolyzing the compound of the formula (XXIV) in the presence of a base.

[0134]

[0135] The symbols in the formula are as defined above.

[0136] Examples of the base include alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, etc.; alkaline earth metal carbonates such as calcium carbonate, barium carbonate, etc.; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, etc.; alkaline earth metal hydroxides such as calcium hydroxide, barium hydroxide, etc. The base can be used in an amount of 0.5 to 10 equivalents per equivalent of the compound of formula (XXIV).

[0137] The reaction of the intermediate production method [2-7] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and may be selected from, 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-pyrrolidone, dimethyl sulfoxide, and sulfolane; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane; alcohols such as methanol, ethanol, and isopropyl alcohol; and water; or a mixture of two or more of these may be used.

[0138] The reaction temperature in the intermediate production method [2-7] is about 0° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0139] Intermediate Production Method [2-8] The compound of formula (XXIV) is commercially available, or can be produced by reacting a compound of formula (XXV) with a compound of formula (VI) in the presence of a base. The compound of formula (XXV) is commercially available.

[0140]

[0141] The symbols in the formula are as defined above.

[0142] The base may be the same as that used in the production method [1], etc. The base can be used in an amount of 0.5 to 10 equivalents per equivalent of the compound of formula (XXV).

[0143] The reaction in the intermediate production method [2-8] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and one or more solvents may be appropriately selected or mixed from the following: 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-pyrrolidone, dimethyl sulfoxide, and sulfolane; nitriles such as acetonitrile and propionitrile; and esters such as ethyl acetate and ethyl propionate.

[0144] The reaction temperature in the intermediate production method [2-8] is about 0° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0145] Intermediate Production Method [2-9] The compound of formula (XXIII) can be produced by reacting a compound of formula (XXVI) with a compound of formula (VI) in the presence of a base. The compound of formula (XXVI) is commercially available.

[0146]

[0147] The symbols in the formula are as defined above.

[0148] Examples of the base include alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, etc.; alkaline earth metal carbonates such as calcium carbonate, barium carbonate, etc.; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, etc.; alkaline earth metal hydroxides such as calcium hydroxide, barium hydroxide, etc.; alkali metal hydrides such as sodium hydride; metal amides such as lithium diisopropylamide, lithium hexamethyldisilazide, potassium hexamethyldisilazide, etc.; metal alkoxides such as sodium methoxide, potassium tert-butoxide, etc. The base can be used in an amount of 0.5 to 10 equivalents per equivalent of the compound of formula (XXVI).

[0149] The reaction of the intermediate production method [2-9] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and one or more solvents may be appropriately selected or mixed from, 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-pyrrolidone, dimethyl sulfoxide, and sulfolane; and water.

[0150] The reaction temperature in the intermediate production method [2-9] is about 20° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0151] Intermediate Production Method [3] The compound of formula (II) can be produced by reacting a compound of formula (XXVII) with a compound of formula (XIX).

[0152]

[0153] The symbols in the formula are as defined above.

[0154] The reaction of the intermediate production method [3] can be carried out in the presence of a base, if necessary. Examples of the base include those similar to those used in the intermediate production method [2]. The base can be used in an amount of 0.5 to 10 equivalents per equivalent of the compound of formula (XXVII).

[0155] The reaction in the intermediate production method [3] can be carried out in the presence of a solvent, if necessary. The solvent may be any solvent inert to the reaction, and is not particularly limited. For example, one or more solvents may be appropriately selected or mixed from the following: 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-pyrrolidone, dimethyl sulfoxide, and sulfolane; 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; and nitroalkanes such as nitromethane and nitroethane.

[0156] The reaction temperature in the intermediate production method [3] is about −20° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0157] Intermediate Production Method [3-1] The compound of formula (XXVII) can be produced by reacting a compound of formula (XX) with a compound of formula (XVI) in the presence of an acid, if necessary. The reaction of Intermediate Production Method [3-1] can be carried out in the same manner as in Intermediate Production Method [2-1].

[0158]

[0159] The symbols in the formula are as defined above.

[0160] Examples of the acid include inorganic acids such as hydrochloric acid, sulfuric acid, etc., and organic acids such as acetic acid, formic acid, methanesulfonic acid, trifluoroacetic acid, p-toluenesulfonic acid, etc. The acid can be used in an amount of 0.1 to 10 equivalents per equivalent of the compound of formula (XX).

[0161] In addition, the compound of formula (XXVII) can be produced in accordance with the description in known literature (for example, Bioorganic and Medicinal Chemistry Letters, 2014, 24, 1944-1947, etc.).

[0162] Intermediate Production Method [4] In the compound of the formula (II), Q is Q ｂ The compound of formula (II-b), which is represented by the formula (II-c), can be produced by reacting a compound of formula (XII) or formula (XXVIII). The compound of formula (XII) or formula (XXVIII) is commercially available or can be produced according to known methods. The reaction of intermediate production method [4] can be carried out in the same manner as in the above-mentioned intermediate production method [1-3].

[0163]

[0164] In the formula, Q ａ Q has at least one chlorine, bromine or iodine as a substituent on the ring １ , Q ２ , Q ３ or Q ４ and Q ｂ Q has at least one alkyl as a substituent on the ring １ , Q ２ , Q ３ or Q ４ and other symbols are as defined above. In addition, in formula (XXVIII), １ may be the same or different.

[0165] Intermediate Production Method [5] Among the compounds of formula (II), the compound of formula (II-d) having cyano as Y can be produced by reacting the compound of formula (II-e) with acetic anhydride.

[0166]

[0167] The symbols in the formula are as defined above.

[0168] The reaction in the intermediate production process [5] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and one or more solvents may be appropriately selected or mixed from, for example, aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; and aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, and sulfolane.

[0169] The reaction temperature in the intermediate production method [5] is about 50° C. to 200° C. The reaction time is about 0.5 to 24 hours.

[0170] In the reaction of intermediate production method [5], a base or a solvent as described below may be added to a vessel during the reaction, if necessary. Furthermore, the mixture obtained after post-treatment or purification of the reaction may be mixed with a base or a solvent as described below. The stirring time after addition of the base or solvent is about 0.5 to 12 hours.

[0171] Examples of the base to be added include those similar to those used in the intermediate production method [2-7]. The base can be used in an amount of 0.5 to 10 equivalents per equivalent of the compound of formula (II-e). In some cases, 10 or more equivalents of the base can be used per equivalent of the compound of formula (II-e).

[0172] The solvent to be added is not particularly limited, and for example, one or more of 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; and water may be appropriately selected or mixed and used.

[0173] Intermediate Production Method [5-1] The compound of formula (II-e) can be produced by reacting the compound of formula (II-f) with hydroxylamine in the presence of a base. The hydroxylamine may be used in the form of a hydroxylamine solution or a hydroxylamine salt.

[0174]

[0175] The symbols in the formula are as defined above.

[0176] Examples of the hydroxylamine solution include an aqueous hydroxylamine solution, a hydroxylamine-ethanol mixed solution, etc. Examples of the hydroxylamine salt include hydroxylamine hydrochloride, hydroxylamine sulfate, etc.

[0177] The base can be used by appropriately selecting one or more 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; acetates such as sodium acetate and potassium acetate; etc. The base can be used in an amount of 0.5 to 10 equivalents per equivalent of the compound of formula (II-f).

[0178] The reaction of the intermediate production method [5-1] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and may be selected from, 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.; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, etc.; alcohols such as methanol, ethanol, isopropyl alcohol, etc.; water; and the like, and one or more of these may be appropriately selected or mixed and used.

[0179] The reaction temperature in the intermediate production method [5-1] is about −20° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0180] Intermediate Production Method [5-2] Among the compounds of formula (II), the compound of formula (II-f) having a formyl group as Y can be produced by reacting a compound of formula (XXIX) with an oxidizing agent.

[0181]

[0182] The symbols in the formula are as defined above.

[0183] Examples of the oxidizing agent include dimethyl sulfoxide-activating agent, 2,2,6,6-tetramethylpiperidine 1-oxyl, 1,1,1-triacetoxy-1,1-dihydro-1,2-benzoiodoxol-3-(1H)-one, manganese dioxide, pyridinium chlorochromate, and pyridinium dichromate.

[0184] In the case of oxidation with dimethyl sulfoxide-activating agent, examples of the activating agent include acid anhydrides such as acetic anhydride and trifluoroacetic anhydride; acid chlorides such as thionyl chloride and oxalyl chloride; chlorine, N-chlorosuccinimide, and the like.

[0185] 2,2,6,6-Tetramethylpiperidine 1-oxyl can be used in a catalytic amount, in which case, for example, sodium hypochlorite, iodobenzene diacetate, or the like is used as a reoxidizing agent.

[0186] The reaction in the intermediate production method [5-2] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and can be selected from, 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.; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, cyclohexane, etc.; ketones such as acetone, ethyl methyl ketone, etc.; alcohols such as methanol, ethanol, isopropyl alcohol, etc.; or the like, and one or more of these can be appropriately selected or mixed and used.

[0187] The reaction temperature in the intermediate production method [5-2] is about −78° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0188] The compound of formula (XXIX) can be produced by reacting the compound of formula (II-g) with a reducing agent. The compound of formula (II-g) can be produced by intermediate production method [2] or intermediate production method [3].

[0189]

[0190] The symbols in the formula are as defined above.

[0191] The reducing agent is not particularly limited, and examples thereof include lithium aluminum hydride, diisobutylaluminum hydride, sodium bis(2-methoxyethoxy)aluminum hydride, sodium borohydride, lithium borohydride, borane-tetrahydrofuran complex, etc. The reducing agent can be used in an amount of 0.5 to 10 equivalents per equivalent of the compound of formula (II-g).

[0192] The reaction in the intermediate production method [5-3] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and can be selected from, for example, halogenated hydrocarbons such as dichloromethane, chloroform, dichloroethane, trichloroethane, carbon tetrachloride, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, etc.; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, cyclohexane, etc.; ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, dimethoxyethane, etc.; alcohols such as methanol, ethanol, isopropyl alcohol, etc.; or the like, and one or more of these can be appropriately selected or mixed and used.

[0193] The reaction temperature in the intermediate production method [5-3] is about −20° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0194] Intermediate Production Method [6] Among the compounds of formula (II), the compound of formula (II-h) in which Z is alkoxyalkyl can be produced by reacting a compound of formula (XXX) with a compound of formula (XXXI) in the presence of a base. The compound of formula (XXXI) is commercially available or can be produced according to known methods.

[0195]

[0196] The symbols in the formula are as defined above.

[0197] Examples of the base include those similar to those used in the above-mentioned production method [1]. The base can be used in an amount of 0.5 to 10 equivalents per equivalent of the compound of formula (XXX).

[0198] The reaction of the intermediate production method [6] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and one or more solvents selected from the same solvents as those used in the above-mentioned production method [1] can be used, or they can be used in combination.

[0199] The reaction temperature in the intermediate production method [6] is about 0° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0200] In the reaction of the intermediate production method [6], a base or water as described below may be added to the vessel during the reaction, if necessary. The stirring time after the addition of the base is about 0.5 to 12 hours.

[0201] Examples of the base to be added include those similar to those used in the intermediate production method [2-7]. The base can be used in an amount of 0.5 to 10 equivalents per equivalent of the compound of formula (XXX). In some cases, 10 or more equivalents of the base can be used per equivalent of the compound of formula (XXX).

[0202] Intermediate Production Method [6-1] The compound of formula (XXX) can be produced by reacting a compound of formula (XXXII) with a reducing agent. The compound of formula (XXXII) can be produced by the intermediate production methods [2] and [2-1], or the intermediate production methods [3] and [3-1], in which Z in formula (I) is -C(=O)OR ｂBy replacing the above with the above, the compound can be produced in accordance with each production method and each intermediate production method.

[0203]

[0204] The symbols in the formula are as defined above.

[0205] The reducing agent is not particularly limited, and examples thereof include lithium aluminum hydride, diisobutylaluminum hydride, sodium bis(2-methoxyethoxy)aluminum hydride, sodium borohydride, lithium borohydride, borane-tetrahydrofuran complex, etc. The reducing agent can be used in an amount of 0.5 to 10 equivalents per equivalent of the compound of formula (XXXII).

[0206] The reaction of the intermediate production method [6-1] can be carried out in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and one or more solvents selected from the same solvents as those used in the intermediate production method [5-3] can be used, or they can be used in combination.

[0207] The reaction temperature in the intermediate production method [6-1] is about −20° C. to 150° C. The reaction time is about 0.5 to 24 hours.

[0208] Among the compounds of formula (II), compounds of formula (II-i) having alkylsulfinyl or alkylsulfonyl as Y can be produced by reacting a compound of formula (II-j) with an oxidizing agent. The compounds of formula (II-j) can be produced by intermediate production method [1] and intermediate production methods [1-1] to [1-4], intermediate production method [2] and intermediate production methods [2-1] to [2-9], or intermediate production method [3] and intermediate production method [3-1].

[0209]

[0210] In the formula, e is 1 or 2, and the other symbols are as defined above.

[0211] Examples of the oxidizing agent include peroxides such as hydrogen peroxide, peracetic acid, perbenzoic acid, metachloroperbenzoic acid, etc. When hydrogen peroxide is used as the oxidizing agent, sodium tungstate, for example, may be added as needed.

[0212] The reaction in the intermediate production process [7] can be carried out in the presence of a solvent, if necessary. The solvent may be any solvent inert to the reaction, and is not particularly limited. For example, one or more solvents may be appropriately selected from, or a mixture of, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aliphatic halogenated hydrocarbons such as methylene chloride, 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-pyrrolidone, dimethyl sulfoxide, and sulfolane; 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.

[0213] The reaction temperature in the intermediate production method [7] is about −20° C. to 100° C. The reaction time is about 0.5 to 24 hours.

[0214] Among the compounds of formula (I), the compound of formula (I-a) having alkylsulfinyl or alkylsulfonyl as Y can be produced by reacting a compound of formula (I-b) with an oxidizing agent. The reaction of the production method [2] can be carried out in the same manner as in the intermediate production method [7].

[0215]

[0216] The symbols in the formula are as defined above.

[0217] Examples of the oxidizing agent include peroxides such as hydrogen peroxide, peracetic acid, perbenzoic acid, metachloroperbenzoic acid, etc. When hydrogen peroxide is used as the oxidizing agent, sodium tungstate, for example, may be added as needed.

[0218] Next, preferred embodiments of pesticides containing the compounds of the present invention are described below. Pesticides containing the compounds of the present invention are useful, for example, as agents for controlling pests, mites, nematodes, or soil pests that are problematic in the agricultural and horticultural fields, i.e., as agricultural and horticultural insecticides, miticides, nematicides, or soil pesticides. They are also useful as agents for controlling animal parasites, i.e., as animal parasite killers.

[0219] Examples of pests that are problematic in the agricultural and horticultural fields include aphids (green peach aphid, cotton aphid, etc.), planthoppers (brown planthoppers, etc.), leafhoppers, scale insects, stink bugs, whiteflies (bean whitefly, etc.), thrips, grasshoppers, flower flies, scarabs, ants, diamondback moths, armyworms, common cutworms, codling moths, ballworms, tobacco budworms, gypsy moths, rice leafrollers, tea Examples of such pests include agricultural pests such as the oriental sawtooth moth, Colorado potato beetle, cucumber beetle, ball weevil, cutthroat moth, turnip moth, etc.; gastropods such as slugs and snails; sanitary pests such as house mites, cockroaches, house flies, Culex pipiens, etc.; grain storage pests such as the box moth, azuki bean weevil, red flour beetle, mealworm beetles, etc.; clothing and house pests such as bur moths, small cutworms, termites, etc. Examples of mites that are problematic in the agricultural and horticultural fields include plant-parasitic mites such as the twospotted spider mite, carmine spider mite, Kanzawa spider mite, citrus red mite, red spider mite, brown mite, citrus rust mite, bulb mite, etc.; and house dust mites such as Tyrophagus putrescentiae, Dermatophagoides farinae, and Chelonia mellifera, etc. Examples of the nematodes that are problematic in the agricultural and horticultural fields include plant-parasitic nematodes such as root-knot nematodes, cyst nematodes, root-lesion nematodes, rice root-lesion nematodes, strawberry root nematodes, and pine wood nematodes. Examples of the soil pests that are problematic in the agricultural and horticultural fields include isopods such as pill bugs and woodlouse.

[0220] The pest control agent containing the compound of the present invention is suitable for controlling, for example, Hemiptera, Thysanoptera, Coleoptera, Acari, Lepidoptera, and Nematoda pests among the above, and is particularly effective for controlling Hemiptera and Acari pests. Specific examples of these pests and nematodes include the following:

[0221] Hemiptera insect pests include the pea aphid (Acyrthosiphon pisum), the Japanese black aphid (Tetraneura nigriabdominalis), the cotton aphid (Ceratovacuna lanigera), the potato aphid (Aulacorthum solani), the radish aphid (Brevicoryne brassicae), the soybean aphid (Aphis glycines), the tulip aphid (Macrosiphum euphorbiae), the corn aphid (Rhopalosiphum maidis), the false radish aphid (Lipaphis erysimi), the barnyard millet aphid (Melanaphis sacchari), the black bean aphid (Aphis fabae), the citrus black aphid (Toxoptera citricida), and the wheat neck aphid (Rhopalosiphum padi), wheat straw aphid (Brachycaudus helichrysi), peach aphid (Myzus persicae), peach butterbur aphid (Hyalopterus pruni), snow willow aphid (Aphis spiraecola), apple aphid (Eriosoma lanigerum), lettuce long-horn aphid (Nasonovia ribisnigri), cotton aphid (Aphis gossypii), European apple aphid (Aphis pomi), English grain aphid (Sitobion avenae), plantain aphid (Dysaphis plantaginea), and other aphids (Aphididae); grape aphid (Daktulosphaira vitifoliae), pecan leaf phylloxera (Phylloxera notabilis), pecan phylloxera (Phylloxera devastatrix), Southern pecan leaf phylloxera (Phylloxera russelae), and other phylloxera (Phylloxeridae);Adelgidae (family Adelgidae) such as Adelges tsugae, Aphrastasia pectinatae, Adelges piceae, etc.; Trialeurodes vaporariorum (family Trialeurodes vaporariorum), Bemisia tabaci (family Bemisia tabaci), Aleurocanthus camelliae (family Aleurocanthus camelliae), Pealius euryae (family Pealius euryae), Dialeurodes citri (family Dialeurodes citri), Aleurocanthus spiniferus (family Aleurodidae), etc.; Javesella pellucida (family Javesella pellucida), Perkinsiella saccharicida (family Perkinsiella saccharicida), Sogatella furcifera (family Sogatella furcifera), etc.; furcifera), corn planthopper (Peregrinus maidis), brown planthopper (Nilaparvata lugens), small brown planthopper (Laodelphax striatellus), rice delphacid (Tagosodes orizicolus), and other planthoppers (Delphacidae); lightning leafhopper (Recilia dorsalis), black-striped rice leafhopper (Nephotettix nigropictus), potato leafhopper (Empoasca fabae), white leafhopper (Cofana spectra), Taiwanese rice leafhopper (Nephotettix virescens), tea green leafhopper (Empoasca onukii), green rice leafhopper (Nephotettix cincticeps), two-spotted green leafhopper (Amrasca biguttula), corn leafhopper (Dalbulus maidis); Aphrophoridae such as European Spittlebug (Philaenus spumarius); Cercopidae such as Mahanarva fimbriolata;Green stink bug (Nezara antennata), Black rice bug (Scotinophara lurida), Large thorny spotted bug (Eysarcoris lewisi), Brown marmorated stink bug (Halyomorpha halys), White spotted bug (Eysarcoris ventralis), Brown-winged green bug (Plautia stali), Thorny spotted bug (Eysarcoris aeneus), Southern green stink bug (Nezara viridula), Purple spotted bug (Eysarcoris annamita), Black paddy bug (Scotinophara coarctata), Brown stink bug (Euschistus heros), Green-berry stink bug (Dichelops melacanthus), Red-banded stink bug (Piezodorus guildinii), rice stink bug (Oebalus pugnax), and other stink bugs (Pentatomidae); ground bugs (Cydnidae) such as the subterraneous stink bug (Scaptocoris castanea); narrow-legged stink bugs (Alydidae) such as the spider stink bug (Leptocorisa chinensis), narrow-legged stink bug (Leptocorisa acuta), and narrow-legged stink bug (Riptortus clavatus); coreid bugs (Coreidae) such as the long-legged stink bug (Leptoglossus australis) and narrow-legged stink bug (Cletus punctiger); American long-legged stink bug (Blissus leucopterus), rice long-legged stink bug (Cavelerius Lygaeidae such as the Japanese long-horned bug (Togo hemipterus) and the Japanese long-horned bug (Togo hemipterus);Miridae (family Miridae) such as the red-striped rice bug (Stenotus rubrovittatus), the red-bearded green rice bug (Trigonotylus caelestialium), the rusty rice bug (Lygus lineolaris), the plain rice bug (Lygus rugulipennis), and the long-spined wheat rice bug (Stenodema calcarata); the red-striped rice scale (Aonidiella aurantii), the plum-white rice scale (Pseudaulacaspis prunicola), the mulberry-white rice scale (Pseudaulacaspis pentagona), the palm-sized rice scale (Abgrallaspis cyanophylli), the pear-sized rice scale (Diaspidiotus perniciosus), and the Yanone rice scale (Unaspis yanonensis) and other round scale insects (Diaspididae); ruby ​​wax moth (Ceroplastes rubens) and other hard scale insects (Coccidae); Icerya purchasi (Icerya seychellarum) and other cotton scale insects (Margarodidae); Pseudococcus calceolariae, Phenacoccus solenopsis, Pseudococcus comstocki, Pseudococcus longispinus, Phenacoccus solani, Planococcus kraunhiae, and Planococcus citri), rice mealybug (Brevennia rehi), and other mealybugs (Pseudococcidae);Psyllidae (Psyllidae) such as potato psyllid (Bactericera cockerelli), Chinese pear psyllid (Cacopsylla chinensis), pear psyllid (Cacopsylla pyrisuga), citrus psyllid (Diaphorina citri), citrus psyllid (Trioza erytreae), and pear sucker (Cacopsylla pyricola); Tingidae (Tingidae) such as goldenrod earwig (Corythucha marmorata), azalea earwig (Stephanitis pyrioides), pear earwig (Stephanitis nashi), and plane tree earwig (Corythucha ciliata); Bedbugs (Cimicidae) such as bedbugs (Cimex lectularius) and netted earwig (Cimex hemipterus); Quesada Cicadas (Cicadidae) such as Triatoma rubrofasciata, Triatoma infestans, Rhodonius prolixus, Triatoma dimidiata, and other assassin bugs (Reduviidae);

[0222] Thrips (Thripidae) such as rice thrips (Stenchaetothrips biformis), tea leaf thrips (Scirtothrips dorsalis), onion thrips (Thrips tabaci), plain flower thrips (Frankliniella intonsa), western flower thrips (Frankliniella occidentalis), southern green thrips (Thrips palmi), white-spotted thrips (Echinothrips americanus), and avocado thrips (Scirtothrips perseae) are classified in the order Thysanoptera; and phlaeothrips (Phlaeothripidae) such as rice phlaeothrips (Haplothrips aculeatus).

[0223] Coleoptera pests include the rice spur beetle (Dicladispa armigera), rice leaf beetle (Oulema oryzae), cucumber beetle (Aulacophora femoralis), striped flea beetle (Phyllotreta striolata), red-necked beetle (Oulema melanopus), Colorado potato beetle (Leptinotarsa ​​decemlineata), sweet potato leaf beetle (Chaetocnema confinis), 18-spotted cucumber beetle (Diabrotica undecimpunctata Mannerheim), tobacco flea beetle (Epitrix hirtipennis), four-spotted tortoise beetle (Laccoptera quadrimaculata), banded cucumber beetle (Diabrotica balteata), bean leaf beetle (Cerotoma trifurcata), and cabbage stem-free beetle (Psylliodes chrysocephala), corn free beetle (Chaetocnema pulicaria), cabbage free beetle (Phyllotreta cruciferae), cucurbit beetle (Diabrotica speciosa), grape colaspis (Colaspis brunnea), hop free beetle (Psylliodes punctulata), northern corn rootworm (Diabrotica barberi), potato free beetle (Epitrix cucumeris), southern corn leaf beetle (Myochrous denticollis), western black free beetle (Phyllotreta pusilla), western corn rootworm (Diabrotica virgifera virgifera), Mexican corn rootworm (Diabrotica virgifera zeae), etc. (Chrysomelidae) beetles; ground beetles (Carabidae) such as slender seed corn beetle (Clivina impressifrons) and seed corn beetle (Stenolophus lecontei);Scarabaeidae such as the green beetle (Anomala albopilosa), the black beetle (Holotrichia kiotonensis), the large black beetle (Holotrichia parallela), the black marmorated beetle (Tomarus gibbosus), the cuprea beetle (Anomala cuprea), the long-legged scarab beetle (Heptophylla picea), the little beetle (Anomala rufocuprea), the Japanese beetle (Popillia japonica), the European chafer (Rhizotrogus majalis), the June beetle (Phyllophaga crinita), the Phyllophaga anxia, ​​the Phyllophaga crassissima, and the Abders' horn beetle (Diloboderus abderus); coffeae); thin-mouthed weevils (Aponidae) such as sweet potato weevil (Cylas formicarius); bean weevils (Bruchidae) such as azuki bean weevil (Callosobruchus chinensis) and Brazilian bean weevil (Zabrotes subfasciatus); bark beetles (Scolytidae) such as pine bark beetle (Tomicus piniperda) and coffee berry borer (Hypothenemus hampei);Alfalfa weevil (Hypera postica), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), potato weevil (Euscepes postfasciatus), granaria weevil (Sitophilus granarius), maize weevil (Sitophilus zeamais), rice weevil (Sitophilus oryzae), rust gourd weevil (Scepticus griseus), grass weevil (Sphenophorus venatus), white grain weevil (Rhabdoscelus lineaticollis), brown gourd weevil (Scepticus uniformis), boll weevil (Anthonomus grandis), cotton root borer (Eutinobothrus brasiliensis), southern cornbill bug (Sphenophorus Weevils (Curculionidae) such as the Japanese mealworm beetle (Sphenophorus levis), the sugarcane weevil (Aracanthus mourei), and the soybean stalk weevil (Sternechus subsignatus); mealworm beetles (Tenebrionidae) such as the Japanese mealworm beetle (Alphitobius diaperinus), the red flour beetle (Tribolium castaneum), and the flat-headed flour beetle (Tribolium confusum); ladybird beetles (Coccinellidae) such as the large 24-spotted ladybird beetle (Epilachna vigintioctomaculata) and the 24-spotted ladybird beetle (Epilachna vigintioctopunctata); long-horn beetles (Bostrychidae) such as Aromia bungii, Anoplophora malasiaca, Migdolus fryanus, and other long-horn beetles (Cerambycidae);Click beetles (Elateridae) such as Okinawan wireworm beetle (Melanotus okinawensis), comb beetle (Melanotus legatus), brown-striped beetle (Agriotes fuscicollis), Aeolus spp., Anchastus spp., Conoderus spp., Ctenicera spp., and Limonius spp.; Staphylinidae beetles such as Paederus fuscipes; Dermestes maculatus, Trogoderma granarium, and Anthrenus Dermestidae beetles such as Stegobium paniceum and Lasioderma serricorne; Anobiidae beetles such as Stegobium paniceum and Lasioderma serricorne; Laemophloeidae beetles such as Cryptolestes ferrugineus; Silvanidae beetles such as Oryzaephilus surinamensis; Nitidulidae beetles such as Brassicogethes aeneus.

[0224] Mites (Tetranychidae) such as Oligonychus spp., Tetranychus kanzawai, Tetranychus urticae, Panonychus citri, Tetranychus evansi, and Panonychus ulmi, which are classified under the order Acari; Aceria diospyri, Shevtchenkella sp., Calacarus carinatus, Acaphylla theavagrans, Aculops lycopersici, Eriophyes chibaensis, Aculops pelekassi, and Phyllocoptruta citri), apple rust mite (Aculus schlechtendali), Aceria tosichella and other Eriophyidae mites; Tarsonemidae mites such as Polyphagotarsonemus latus; Tenuipalpidae mites such as Brevipalpus phoenicis; Tuckerellidae mites; Acaridae mites such as Tyrophagus putrescentiae and Tyrophagus similis; Pyroglyphidae mites such as Dermatophagoides farinae and Dermatophagoides pteronyssinus.

[0225] Lepidoptera insect pests include the rice grain borer (Ostrinia scapulalis), the European corn borer (Ostrinia furnacalis), the rice leaf borer (Scirpophaga incertulas), the rice casino borer (Marasmia exigua), the rice leaf borer (Cnaphalocrocis medinalis), the grass leaf borer (Pediasia teterrellus), the rice suppressor borer (Chilo suppressalis), the brown spotted borer (Hellula undalis), the rice black borer (Herpetogramma luctuosale), the cotton borer (Haritalodes derogata), the dark-headed striped borer (Chilo polychrysus), the rice water borer (Nymphula depunctalis), the rice white borer (Scirpophaga innotata), and the sugarcane borer (Diatraea Crambidae moths such as Ephestia kuehniella, Cadra cautella, Plodia interpunctella, Euzophera batangensis, Elasmopalpus lignosellus, etc.; Pyralidae moths such as Ephestia kuehniella, Cadra cautella, Plodia interpunctella, Euzophera batangensis, Elasmopalpus lignosellus, etc.;African armyworm (Spodoptera exempta), armyworm (Mythimna separata), rice yellow looper (Plusia festucae), rice armyworm (Sesamia inferens), beet armyworm (Spodoptera exigua), armyworm (Spodoptera mauritia), silver armyworm (Autographa nigrisigna), cutworm moth (Agrotis ipsilon), leaf fall armyworm (Spodoptera frugiperda), false tobacco budworm (Heliothis virescens), common cutworm (Spodoptera litura), two-banded cutworm (Naranga aenescens), armyworm moth (Mamestra brassicae), southern armyworm (Spodoptera eridania), soybean looper (Chrysodeixis includens), Spodoptera Noctuidae moths such as Trichoplusia spp., Helicoverpa zea, Helicoverpa armigera, Trichoplusia ni, Agrotis segetum, Spodoptera depravata, Helicoverpa assulta, Aedia leucomelas, African pink stem borer, Sesamia calamistis, cotton leafworm, Hydraecia immanis, soybean looper, Pseudoplusia includens, and velvetbean caterpillar; Pieris brassicae, Pieris Pieridae, such as Pieridae;Tortricidae moths (Tortricidae) such as Matsumuraeses azukivora, Archips xylosteanus, Tetramoera schistaceana, Cydia pomonella, Grapholita dimorpha, Adoxophyes honmai, Homona magnanima, Grapholita molesta, Leguminivore moth (Leguminivora glycinivorella), Archips fuscocupreanus, Adoxophyes orana fasciata, Citrus fruit borer (Citripestis sagittiferella), Grapeberry moth (Lobesia botrana), and Epinotia aporema; Gracilaria moths (Gracillariidae) such as Caloptilia ringoniella, Caloptilia theivora, and citrus leafminer moth (Phyllocnistis citrella); Carposinidae moths such as Carposina sasakii; Lyonetiidae moths such as Lyonettia prunifoliella, Lyonettia clerkella, and coffee leaf miner (Leucoptera coffeella); Lymantriidae moths such as Lymantria dispar and Euproctis pseudoconspersa; Plutella xylostella and other diamondback moths (Plutellidae);Gelechiidae moths such as the potato moth (Helcystogramma triannulella), potato tuber moth (Pthorimaea operculella), tomato moth (Tuta absoluta), peach moth (Anarsia lineatella), and red bollworm moth (Pectinophora gossypiella); Arctiidae moths such as the American fall webworm (Hyphantria cunea); Castniidae moths such as the giant sugarcane borer (Telchin licus); Cossidae moths such as the little box moth (Cossus insularis); Geometridae moths such as the plum geometridae (Cystidia couaggaria) and the mugwort geometridae (Ascotis selenaria); Parasa consocia moths, Monema Limacodidae moths such as Parasa lepida and Parasa flavescens; Stathmopodidae moths such as Stathmopoda masinissa; Sphingidae moths such as Acherontia lachesis; Sesiidae moths such as Nokona feralis, Synanthedon hector, and Synanthedon tenuis; Hesperiidae butterflies such as Parnara guttata; Tineidae moths such as Tinea translucens and Tineola bisselliella; Papilio xuthus and Papilio machaon swallowtail butterflies (Papilionidae) such as hippocrates;

[0226] Nematodes include the Aphelenchoididae, such as the rice root-lesion nematode (Aphelenchoides besseyi); the Pratylenchidae, such as the northern root-lesion nematode (Pratylenchus penetrans), the southern root-lesion nematode (Pratylenchus coffeae), the wheat root-lesion nematode (Pratylenchus neglectus), the wheat root-lesion nematode (Pratylenchus brachyurus), and the wheat root-lesion nematode (Radopholus similis); the northern root-knot nematode (Meloidogyne hapla), the sweet potato root-knot nematode (Meloidogyne incognita), the Java root-knot nematode (Meloidogyne javanica), the potato cyst nematode (Globodera rostochiensis), and the potato white cyst nematode (Globodera Heteroderidae such as Heterodera pallida, soybean cyst nematode (Heterodera glycines), and guava root-knot nematodes (Meloidogyne enterolobii); Hoplolaimidae such as Rotylenchulus reniformis; Anguinidae such as strawberry root nematode (Nothotylenchus acris) and stalk nematode (Ditylenchus dipsaci); Tylenchulidae such as citrus root nematode (Tylenchulus semipenetrans); Longidoridae such as grape nematode (Xiphinema index); Trichodoridae; Parasitaphelenchidae such as pine wood nematode (Bursaphelenchus xylophilus).

[0227] Agricultural and horticultural insecticides, miticides, nematicides, or soil pesticides containing the compounds of the present invention are particularly effective in controlling plant-parasitic mites, agricultural pests, plant-parasitic nematodes, etc. Among them, they are particularly effective in controlling plant-parasitic mites and agricultural pests, and are therefore very useful as insecticides or miticides. In addition, agricultural and horticultural insecticides, miticides, nematicides, or soil pesticides containing the compounds of the present invention are also effective in controlling various pests resistant to existing pesticides such as organophosphates, carbamates, synthetic pyrethroids, and neonicotinoids. Furthermore, since the compounds of the present invention have excellent systemic and translocating properties, applying agricultural and horticultural insecticides, miticides, nematicides, or soil pesticides containing the compounds of the present invention to soil can control soil-harming insects, mites, nematodes, gastropods, and isopods, as well as stem and leaf pests.

[0228] Another desirable embodiment 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 above-mentioned agricultural pests, gastropods, plant-parasitic mites, plant-parasitic nematodes, soil pests, etc.

[0229] The pest control agent containing the compound of the present invention is effective against, for example, fruit vegetables such as tomatoes, cherry tomatoes, bell peppers, eggplants, cucumbers, zucchinis, watermelons, melons, pumpkins, okra, chili peppers, Chinese gourds, wax gourds, bitter melons, and Japanese cantaloupes; lettuce, leaf lettuce, spinach, cabbage, onions, garlic, asparagus, broccoli, cauliflower, Chinese cabbage, morning glory, leeks, mizuna, shiso, komatsuna, Leafy vegetables such as celery; root vegetables such as potatoes, sweet potatoes, radishes, carrots, burdock, lotus root, taro, konjac, yam, ginger, turnip, shallot, myoga, and wood thistle; beans such as soybeans, adzuki beans, peas, kidney beans, peanuts, broad beans, and edamame; grains such as rice, wheat, oats, rye, and corn; apples, citrus fruits, pears, grapes, strawberries, and cucumbers. It can be used for agricultural and horticulturally useful plants such as fruit trees, fruits, and nuts such as rumi, almonds, bananas, figs, pineapples, peaches, nectarines, cherries, apricots, coconuts, avocados, persimmons, plums, pistachios, kiwifruit, and loquats; turf grass such as Korean lawn grass and bentgrass; flowering plants such as chrysanthemums, lilies, roses, carnations, dahlias, gerberas, saintpaulia, tulips, daffodils, petunias, lily of the valley, peonies, cyclamen, impatiens, and lisianthus; flowering trees such as azaleas; industrial crops such as cotton, rapeseed, beets, tea, tobacco, coffee, olives, sugarcane, hops, sesame, parsley, thyme, rosemary, basil, and lavender; ornamental plants such as orchids, cacti, and ferns; and pasture plants such as clover, alfalfa, orchardgrass, and Johnsongrass.

[0230] These plants include plants that have been conferred resistance 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, etc.) by classical breeding methods. Furthermore, transformed plants produced by genetic engineering techniques or gene editing techniques are also included. Examples of transformed plants include transformed plants that are resistant to the above-mentioned herbicides, transformed plants that are resistant to pests, transformed plants related to plant components, and transformed plants that are resistant to plant pathogens.

[0231] Pesticides containing the compounds of the present invention are usually formulated by mixing the compounds with various adjuvants and using them in various forms such as dusts, granules, water-dispersible granules, wettable powders, aqueous suspensions, oily suspensions, water-soluble granules, water-soluble granules, emulsions, liquids, pastes, aerosols, and micro-sprays. However, as long as the purpose of the present invention is met, any formulation form commonly used in the field can be used. Examples of adjuvants used in formulations include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, baking soda, sodium sulfate, zeolite, and starch; solvents such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, and alcohol; fatty acid salts, benzoates, alkyl sulfosuccinates, dialkyl sulfosuccinates, polycarboxylates, alkyl sulfates, alkyl sulfates, alkylaryl sulfates, and alkane. anionic surfactants such as alkyl diglycol ether sulfate, alcohol sulfate, alkyl sulfonate, alkylaryl sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate, alkylaryl phosphate, styrylaryl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkylaryl ether sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkylaryl phosphate, and naphthalene sulfonate formaldehyde condensate;Examples of suitable surfactants include nonionic surfactants such as sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polyglycerides, fatty acid alcohol polyglycol ethers, acetylene glycol, acetylene alcohol, oxyalkylene block polymers, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene styrylaryl ethers, polyoxyethylene glycol alkyl ethers, polyethylene glycol, polyoxyethylene fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyoxyethylene hydrogenated castor oil, and polyoxypropylene fatty acid esters; vegetable oils and mineral oils such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil, and liquid paraffin; and silicone oils. As long as the objectives of the present invention are not exceeded, one or more of these adjuvant components may be appropriately selected and used. In addition to the above-mentioned adjuvants, any adjuvant known in the art may be appropriately selected and used. For example, various commonly used adjuvants such as bulking agents, thickeners, antisettling agents, antifreezing agents, dispersion stabilizers, phytotoxicity reducers, and antifungal agents may also be used. The blending ratio (weight ratio) of the compound of the present invention to the various adjuvants is 0.001:99.999 to 95:5, preferably 0.005:99.995 to 90:10. When actually using these formulations, they can be used as is or diluted with a diluent such as water to a predetermined concentration, and various spreading agents (surfactants, vegetable oil, mineral oil, etc.) can be added as needed.

[0232] Although the application of the pesticide containing the compound of the present invention cannot be categorically defined due to differences in weather conditions, formulation form, application time, application location, type and occurrence of pests, etc., it is generally carried out at a concentration of 0.1 to 50,000 ppm, preferably 1 to 30,000 ppm, of the active ingredient, and the application amount 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 a method for controlling pests, mites, nematodes or soil pests, particularly a method for controlling plant-parasitic mites, agricultural pests and plant-parasitic nematodes, using such an application method.

[0233] Various formulations of pesticides containing the compounds of the present invention or their dilutions can be applied by commonly used application methods, i.e., spraying (e.g., spraying, misting, atomizing, granulation, water application, etc.), soil application (mixing, irrigation, etc.), surface application (painting, dusting, covering, etc.), and immersion poison bait. It is also possible to mix the active ingredient with livestock feed and feed it to inhibit the emergence and growth of pests, particularly harmful insects, in their excrement. It can also be applied by the so-called ultra-low volume application method. This method allows the active ingredient to be contained at 100%.

[0234] For example, when a pesticide containing the compound of the present invention is applied to a plant, pests can be controlled by applying an effective amount of the pesticide directly to pests such as insects, mites, nematodes, and soil pests, and / or to the soil or plant body. The plant body refers to the above-ground parts (e.g., stems, leaves, trunks), underground parts (e.g., roots), or seeds of the plant to which the pesticide is applied. The seed refers to propagules (so-called seeds) formed by sexual reproduction, plant organs (e.g., tubers, bulbs, corms, rhizomes, seed potatoes), or cuttings of fruit trees, flowering trees, or ornamental plants (e.g., grapevine branches, which are fruit trees).

[0235] In this case, the application of the pesticide containing the compound of the present invention to plants can be carried out, for example, by soil treatment, foliage treatment, drench treatment, seed treatment, trunk injection treatment, or application to rice seedling boxes. Generally, in the case of soil treatment, foliage treatment, or drench treatment, the appropriate application amount of the compound of the present invention per hectare can be 0.01 g to 50,000 g, preferably 1 g to 30,000 g. In the case of seed treatment, the appropriate application amount can be 0.01 g to 200 g, preferably 0.05 to 100 g, per kg of seeds. In the case of application to rice seedling boxes, the appropriate application amount can be 0.001 g to 3,000 g, preferably 0.01 g to 1,000 g, of the compound of the present invention per seedling box. In the case of trunk injection treatment, the appropriate application amount of the compound of the present invention per tree can be about 0.001 g to 5,000 g, preferably about 0.01 g to 3,000 g.

[0236] In the above, examples of soil treatment include a method in which the compound of the present invention is prepared into a liquid formulation (a solution, an aqueous suspension, an oily suspension, an emulsion, etc.) or a solid formulation (a granule, a dust, a wettable powder, a water-soluble powder, a water-dispersible granule, a water-soluble granule, etc.), and then sprayed or diluted with water over the entire surface of the soil before transplanting or sowing plants, and mixed; a method in which the compound is sprayed into a hole opened for planting plants (a planting hole); or a method in which the compound is sprayed into a shallow trench dug to a certain width for sowing or planting plants.

[0237] Examples of foliar treatment include a method in which the compound of the present invention is prepared into a liquid formulation (such as a liquid agent, an aqueous suspension, an oily suspension, or an emulsion) or a solid formulation (such as a wettable powder, a water-soluble powder, a water-dispersible granule, or a water-soluble granule), diluted with water, and sprayed over the entire plant body.

[0238] Examples of irrigation treatment include a method in which the compound of the present invention is prepared into a liquid formulation (such as a liquid agent, an aqueous suspension, or an oily suspension) or a solid formulation (such as a wettable powder, a water-soluble powder, a water-dispersible granule, or a water-soluble granule), and then irrigated directly or after diluting with water into a cultivation container for raising seedlings, the base of a plant under cultivation, or the vicinity thereof.

[0239] Seed treatment may involve, for example, preparing the compound of the present invention into a liquid formulation (aqueous suspension, oily suspension, emulsion, solution, etc.) or a solid formulation (dust, wettable powder, water-soluble powder, water-dispersible granules, water-soluble granules, etc.), and stirring the formulation with seeds as is or after diluting it in water to allow it to adhere to the seed surface; mixing the formulation with a coating material to allow it to adhere to the seed surface; spraying the formulation onto seeds; or soaking seeds to allow the formulation to penetrate the seeds.

[0240] Application to rice seedling boxes includes, for example, a method in which the compound of the present invention is prepared into a solid formulation (granules, dust, etc.) or a liquid formulation (aqueous suspension, oily suspension, liquid, etc.), and then sprayed directly or diluted with water onto the seedling boxes before sowing, after sowing, both before and after sowing, during growth in the seedling boxes, or before transplanting to a paddy field. Also included is a method in which the compound of the present invention is mixed with the soil at the time of sowing into the seedling boxes, for example, the compound of the present invention is prepared into a solid formulation (granules, dust, water dispersible granules, etc.) and then mixed with the entire bed soil, covering soil, or soil.

[0241] Examples of trunk injection treatment include a method in which the compound of the present invention is prepared into a liquid formulation (such as a liquid agent) and then directly injected into the plant body through a hole drilled in the trunk.

[0242] In addition, agricultural and horticultural insecticides, acaricides, nematicides, or soil pesticides containing the compound of the present invention can be mixed or used in combination with other pesticides, fertilizers, phytotoxicity safeners, etc., and in this case, even more excellent effects and activity may be exhibited. The term "mixed or used in combination" means that the compound of the present invention and other ingredients are used simultaneously, separately, or at intervals. Examples of other pesticides include herbicides, insecticides, acaricides, nematicides, soil pesticides, fungicides, antivirals, attractants, antibiotics, plant hormones, and plant growth regulators. In particular, insecticidal compositions, acaricidal compositions, nematicidal compositions, or soil pesticidal compositions containing the compound of the present invention mixed or used in combination with one or more active ingredient compounds of other pesticides can favorably improve the scope of application, timing of chemical treatment, control activity, etc. The compound of the present invention and the active ingredient compounds of other pesticides may be formulated separately and mixed for application, or both may be formulated together for application. The present invention also includes such insecticidal compositions, acaricidal compositions, nematicidal compositions, or soil pesticidal compositions.

[0243] The mixing ratio of the compound of the present invention to the active ingredient compounds of other insecticides and / or nematicides (compound of the present invention:other active ingredient compounds) cannot be generally determined due to differences in weather conditions, formulation form, target crops, application time, application location, and the type and occurrence of pests or nematodes, but is generally 1:300 to 300:1, and preferably 1:100 to 100:1, by weight. The appropriate application amount is 0.1 to 70,000 g, preferably 5 to 50,000 g, of the total active ingredient compounds per hectare. The present invention also includes a method for controlling pests and nematodes by applying such a mixed insecticidal and nematicidal composition.

[0244] Among the above other agricultural chemicals, the insecticides, acaricides, nematicides or soil pesticides, i.e., the active ingredient compounds of the insecticides (common names or Japan Plant Protection Association test codes), can be appropriately selected, for example, from the following compound groups. Even if not specifically stated, when these compounds have salts, alkyl esters, optical isomers or other structural isomers, these are of course included.

[0245] Profenofos, dichlorvos, fenamiphos, fenitrothion, EPN ((RS)-(O-ethyl O-4-nitrophenylphenylphosphonothioate), diazinon (diazinon), chlorpyrifos (chlorpyrifos), chlorpyrifos-methyl (chlorpyrifos-methyl), acephate (acephate), prothiofos (prothiofos), fosthiazate (fosthiazate), cadusafos (cadusafos), disulfoton (disulfoton), isoxathion (isoxathion), isofenphos (isofenphos), ethion (ethion), etrimfos (etrimfos), quinalphos (quinalphos), dimethylvinphos (dimethylvinphos), dimethoate (dimethoate), sulprofos (sulprofos), thiometon (thiometon), vamidothion (vamidothion), pyraclofos (pyraclofos), pyridaphenthion (pyridaphenthion), pirimiphos-methyl (pirimiphos-methyl), propaphos (propaphos), phosalone (phosalone), formothion (for organophosphate ester compounds such as mothion, malathion, tetrachlorvinphos, chlorfenvinphos, cyanophos, trichlorfon, methidathion, phenthoate, oxydeprofos (also known as ESP), azinphos-methyl, fenthion, heptenophos, parathion, phosphocarb, demeton-S-methyl, monocrotophos, methamidophos, imicyafos, parathion-methyl, terbufos, phosphamidon, phosmet, and phorate;Carbamate compounds such as carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, carbosulfan, benfuracarb, bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb, 3,5-xylyl methylcarbamate (XMC), and fenothiocarb;

[0246] Nereistoxin derivatives such as cartap, thiocyclam, thiocyclam oxalate, thiocyclam hydrochloride, bensultap, thiosultap, monosultap (also known as thiosultap-monosodium), bisultap (also known as thiosultap-disodium), and polythialan; organochlorines such as dicofol, tetradifon, endosulfan, dienochlor, dieldrin, and methoxychlor; organotin compounds such as fenbutatin oxide, cyhexatin, and azocyclotin; Fenvalerate, permethrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, theta-cypermethrin, beta-cypermethrin, deltamethrin, cyhalothrin, gamma-cypermethrin gamma-cyhalothrin, lambda-cyhalothrin, tefluthrin, kappa-tefluthrin, etofenprox, flufenprox, cyfluthrin, beta-cyfluthrin, fenpropathrin, flucythrinate,Fluvalinate, cycloprothrin, pyrethrins, esfenvalerate, tetramethrin, resmethrin, protrifenbute, bifenthrin, kappa-bifenthrin, acrinathrin, allethrin, tau-fluvalinate, tralomethrin pyrethroids such as lomethrin, profluthrin, metofluthrin, epsilon-metofluthrin, heptafluthrin, phenothrin, flumethrin, momfluorothrin, epsilon-momfluorothrin, silafluofen, chloroprallethrin;

[0247] Benzoylurea compounds such as diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron, novaluron, triflumuron, hexaflumuron, bistrifluron, noviflumuron, fluazuron, and flufenoxuron; juvenile hormone-like 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; Pyrazolecarboxamide compounds such as piflubumide, tebufenpyrad, tolfenpyrad, and dimpropyridaz;pyridylpyrazole compounds such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetrachlorantraniliprole, tetraniliprole, tyclopyrazoflor, fluchlordiniliprole, thiolantraniliprole, and pioxaniliprole;

[0248] 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; Tetramic acid compounds such as spirotetramat, spiropidione, and spidoxamat; Strobilurin compounds such as fluacrypyrim, pyriminostrobin, and flupyroxystrobin; Pyrimidinamine compounds such as flufenerim and pyrimidifen; Organic sulfur compounds such as malathion; Triazine compounds such as cyromazine; Hydrazone compounds such as hydramethylnon; Phthalamide compounds such as flubendiamide and cyhalodiamide;

[0249] Metadiamide compounds such as broflanilide, cyproflanilide, modoflaner, and piperflanilide; Thiourea compounds such as diafenthiuron and chloromethiuron; Formamidine compounds such as amitraz, chlordimeform, and chloromebuform; Pyridine azomethine compounds such as pymetrozine and pyrifluquinazon; Isoxazoline compounds such as afoxolaner, fluralaner, fluxametamide, sarolaner, isocycloseram, umifoxolaner, tigolaner, mivorilaner, and isoflualanam; fluoroalkenyl compounds such as fluensulfone and trifluenfuronate;

[0250] Mesoionic compounds such as dichloromezotiaz, triflumezopyrim, and fenmezoditiaz; Pyropene compounds such as afidopyropen;Other compounds include buprofezin, hexythiazox, triazamate, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, 1,3-dichloropropene, benclothiazol, bifenazate, propargite, clofentezine, metaflumizone, cyflumetofen, fenazaquin, amidoflumet, sulfuramid, hydramethylnon, metaldehyde, and sulfoxaflor. Compounds such as lfoxaflor, verbutin, fluhexafon, tioxazafen, flometoquin, flupyradifurone, fluazaindolizine, acinonapyr, benzpyrimoxan, flupyrimin, oxazosulfyl, cyclobutrifluram, flupentiofenox, indazapyroxamet, sulfiflumin, bisulfufen, cybenzoxasulfyl, thiapyrachlor, bentiofluorin, and the like;

[0251] They may also be combined with the following compounds: microbial pesticides such as crystal protein toxins produced by 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 virus agents, insect pathogenic fungi agents, nematode pathogenic fungi agents, etc.;

[0252] Antibiotics and semi-synthetic antibiotics such as abamectin, emamectin benzoate, ivermectin, milbemectin, milbemycin oxime, lepimectin, spinosad, spinetoram; natural products such as azadirachtin, rotenone, ryanodine; repellents such as deet; physical control agents such as paraffin oil, mineral oil; RNAi pesticides such as ledprona.

[0253] Among the above other pesticides, the active ingredient compounds of fungicides (generic names or Japan Plant Protection Association test codes) can be appropriately selected from, for example, the following compound groups. Even if not specifically stated, when these compounds have various structural isomers such as salts, alkyl esters, and optical isomers, these are also included. Anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, and cyprodinil; Triazolopyrimidine compounds such as ametoctradin; Triazolobenzothiazole compounds such as tricyclazole; Pyridinamine compounds such as fluazinam;Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, fluconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, oxpoconazole fumarate azole compounds such as fumarate, prothioconazole, triadimenol, flutriafol, difenoconazole, fluquinconazole, fenbuconazole, bromuconazole, diniconazole, simeconazole, pefurazoate, ipconazole, imibenconazole, azaconazole, triticonazole, imazalil, ipfentrifluconazole, mefentrifluconazole, and fluoxytioconazole; quinoxaline compounds such as chinomethionate;

[0254] Dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, and thiram; organochlorine compounds such as phthalide, chlorothalonil, and quintozene; 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 chiralaxyl or chiralaxyl), furalaxyl, and valifenalate; Anilide compounds such as cyprofuram, carboxin, oxycarboxin, thifluzamide, boscalid, fenhexamid, isotianil, tiadinil, and pyraziflumid;

[0255] Sulfamide (sulfenic acid) compounds such as dichlofluanid and tolylfluanid; Copper compounds such as cupric hydroxide, organocopper (oxine copper), anhydrous copper sulfate, copper nonylphenolsulfonate, 8-hydroxyquinoline copper, and dodecylbenzenesulfonate bisethylenediamine copper complex(II) (also known as DBEDC); Organophosphate compounds such as fosetyl aluminum, tolclofos-methyl, edifenphos, and iprobenfos; Phthalimide compounds such as captan, captafol, and folpet; Dicarboximide compounds such as procymidone, iprodione, and vinclozolin;

[0256] benzanilide compounds such as flutolanil, mepronil, benodanil, and flufenoxadiazam; amide compounds such as carpropamid, diclocymet, silthiofam, and fenoxanil; pyrazolecarboxamide compounds such as benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, pydiflumetofen, sedaxane, isoflucypram, inpyrfluxam, pyrapropoyne, and flubeneteram;

[0257] Benzamide compounds such as fluopicolide, fluopyram, zoxamide, and fluopimomide; Furanilide compounds such as fenfuram; Thiophenamide compounds such as isofetamide; Piperazine compounds such as triforine; Pyridine compounds such as pyrifenox, pyrisoxazole, and aminopyrifen; Pyrimidine compounds such as fenarimol, ferimzone, nuarimol, and flumethylsulforim; Piperidine compounds such as fenpropidin; Morpholine compounds such as fenpropimorph and tridemorph; Organotin compounds such as triphenyltin hydroxide and triphenyltin acetate; urea compounds such as pencycuron;

[0258] 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; strobilurin compounds such as azoxystrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, picoxystrobin, orysastrobin, dimoxystrobin, pyraclostrobin, fluoxastrobin, pyraoxystrobin, pyrametostrobin, coumoxystrobin, enoxastrobin, phenaminestrobin, flufenoxystrobin, triclopyricarb, and mandestrobin;

[0259] Oxazole compounds such as famoxadone, oxathiapiprolin, and fluoxapiprolin; Thiazolecarboxamide 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;

[0260] Quinoline compounds such as tebufloquine, quinoxyfen, quinofumelin, and ipflufenoquin; Thiazolidine compounds such as flutianil; Carbamate compounds such as propamocarb hydrochloride, pyribencarb, and tolprocarb; Tetrazole compounds such as picarbutrazox and methyltetraprole; Sulfonamide compounds such as amisulbrom and cyazofamid; Allyl phenyl ketone compounds such as metrafenone and pyriophenone; Benzothiazole compounds such as probenazole and dichlobentiazox; Phenylpyrazole compounds such as fenpyrazamine; Dithiolane compounds such as isoprothiolane; Picolinamide compounds such as fenpicoxamid, florylpicoxamid, and metarylpicoxamid; Pyridazine compounds such as pyridachlometyl; Sulfur compounds such as sulfur and lime sulfur; Hydrazide compounds such as chloroinconazide;

[0261] Other compounds include pyroquilon, diclomezine, chloropicrin, dazomet, metam sodium, proquinazid, spiroxamine, dipymetitrone, fenopyramide, and feneptamidoquin; microbial disinfectants such as Bacillus amylolicophae strain QST713, Bacillus amylolicophae strain FZB24, Bacillus amylolicophae strain MBI600, Bacillus amylolicophae strain D747, Pseudomonas fluorescens, Bacillus subtilis, and Trichoderma atroviride SKT-1; and plant extracts such as tea tree oil.

[0262] Some preferred embodiments of the present invention will be exemplified below, but the present invention is not limited to these.

[0263] (1) A pyridazinone compound represented by the formula (I) or a salt thereof. (2) Y and R Ａ each represents a halogen, an alkyl, an alkenyl, an alkynyl, a cycloalkyl, a haloalkyl, an alkoxy, a haloalkoxy, an alkylsulfonyl, a cyano, or —C(═O)R Ｂ (3) The pyridazinone compound or a salt thereof according to (1), wherein Y and R Ａ 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 １ -C ４ ) haloalkoxy, (C １ -C ４ ) alkylthio, (C １ -C ４ ) alkylsulfinyl, (C １ -C ４ ) alkylsulfonyl, cyano or —C(═O)R Ｂ Z is (C １ -C ５ ) alkyl, (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 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 -C４ ) haloalkylsulfonyl, cyano, nitro, aldehyde, -CH(=NOR Ｃ ), 1,3-dioxan-2-yl or 1,3-dioxolan-2-yl; R Ｂ is a hydrogen atom or (C １ -C ４ ) alkyl; R Ｃ (C １ -C ４ ) alkyl; G is R Ｄ (C １ -C ４ ) alkyl, —C(═O)E or (C １ -C ４ ) alkylsulfonyl; R Ｄ (C １ -C ４ ) alkoxy, cyano, (C １ -C ４ ) alkoxycarbonyl or (C １ -C ４ ) alkoxycarbonyloxy; E is (C １ -C ８ ) alkyl, (C ２ -C ８ ) alkenyl, (C ３ -C ６ ) cycloalkyl, heterocycloalkyl, (C １ -C ８ ) haloalkyl, (C ２ -C ８ ) haloalkenyl, (C １ -C ４ ) dialkylamino, N—(C １ -C ４ ) alkoxy-N—(C １ -C ４ ) alkylamino, V Ａ phenyl optionally substituted with V Ａ pyridyl optionally substituted with (C ３ -C ６ ) cycloalkyl (C １ -C ４ ) alkyl, heterocycloalkyl (C １ -C ４ ) alkyl, (C １ -C４ ) alkoxy(C １ -C ３ ) alkyl, (C １ -C ４ ) alkylthio (C １ -C ３ ) alkyl, V Ａ phenyl (C １ -C ４ ) alkyl, V Ａ phenyloxy (C １ -C ３ ) alkyl, V Ａ phenyl (C ２ -C ４ ) alkenyl, (C １ -C ７ ) alkoxy, (C ２ -C ７ ) alkenyloxy, (C ２ -C ７ ) alkynyloxy, (C ３ -C ６ ) cycloalkyloxy, heterocycloalkyloxy, (C １ -C ７ ) haloalkoxy, (C １ -C ４ ) alkoxy(C １ -C ３ ) Alkoxy, V Ａ phenyloxy optionally substituted with V Ａ naphthyloxy optionally substituted with (C ３ -C ６ ) cycloalkyl (C １ -C ３ ) alkoxy, heterocycloalkyl (C １ -C ３ ) Alkoxy, V Ｂ phenyl (C １ -C ３ ) alkoxy, (C １ -C ７ ) alkylthio or 2-imidazolidinone, and the heterocycloalkyl and heterocycloalkyl moiety in E are each a 3- to 6-membered group containing, in addition to carbon atoms, one or more atoms of one or more kinds selected from oxygen atoms, nitrogen atoms, and sulfur atoms; VＢ is halogen or (C １ -C ４ (4) The pyridazinone compound or salt thereof according to (1), wherein Y and R are alkyl. Ａ 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 １ -C ４ ) haloalkoxy, (C １ -C ４ ) alkylsulfonyl, cyano or —C(═O)R Ｂ The pyridazinone compound or a salt thereof according to (3),

[0264] (5) 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 ４ ) haloalkyl; R １ , R ２ , R ３ and R ４ are 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 -C４ ) alkylsulfinyl, (C １ -C ４ ) alkylsulfonyl, cyano, nitro, aldehyde, -CH(=NOR Ｃ ) or 1,3-dioxolan-2-yl; E is (C １ -C ８ ) alkyl, (C ２ -C ８ ) alkenyl, (C ３ -C ６ ) cycloalkyl, heterocycloalkyl, (C １ -C ８ ) haloalkyl, (C １ -C ４ ) dialkylamino, N—(C １ -C ４ ) alkoxy-N—(C １ -C ４ ) alkylamino, V Ａ phenyl optionally substituted with V Ａ pyridyl optionally substituted with (C ３ -C ６ ) cycloalkyl (C １ -C ４ ) alkyl, heterocycloalkyl (C １ -C ４ ) alkyl, (C １ -C ４ ) alkoxy(C １ -C ３ ) alkyl, (C １ -C ４ ) alkylthio (C １ -C ３ ) alkyl, V Ａ phenyl (C １ -C ４ ) alkyl, V Ａ phenyloxy (C １ -C ３ ) alkyl, V Ａ phenyl (C ２ -C ４ ) alkenyl, (C １ -C ７ ) alkoxy, (C ２ -C ７ ) alkenyloxy, (C２ -C ７ ) alkynyloxy, (C ３ -C ６ ) cycloalkyloxy, (C １ -C ７ ) haloalkoxy, (C １ -C ４ ) alkoxy(C １ -C ３ ) Alkoxy, V Ａ phenyloxy optionally substituted with V Ａ naphthyloxy optionally substituted by V Ｂ phenyl (C １ -C ３ ) alkoxy, (C １ -C ７ (6) The pyridazinone compound or salt thereof according to (3) or (4), wherein Q is alkylthio or 2-imidazolidinone, and the heterocycloalkyl and heterocycloalkyl moiety in E are each a 3- to 6-membered group containing, in addition to carbon atoms, one or more atoms of one or more kinds selected from oxygen atoms, nitrogen atoms, and sulfur atoms. １ or Q ３ (7) The pyridazinone compound or salt thereof according to any one of (1) to (5), wherein X is CH or C(R Ａ (8) The pyridazinone compound or a salt thereof according to any one of (1) to (6), wherein X is C(R Ａ (9) A pyridazinone compound or a salt thereof according to any one of (1) to (6), wherein X is CH. (10) A pyridazinone compound or a salt thereof according to any one of (1) to (6), wherein X is N. (11) A pyridazinone compound or a salt thereof according to any one of (1) to (6), wherein X is C(R Ａ (12) When X is CH, n is an integer of 1 to 3, and X is C(R Ａ) or, in the case of N, n is 1 or 2, and when n is N, n is 1 or 2, and when n is N, n is 1 or 2, and when n is N, n is 2 or 3 ... (20) The pyridazinone compound according to (19) represented by the formula (iii-c) or a salt thereof. (21) The pyridazinone compound according to (19) or a salt thereof, wherein c is 1 or 2. (22) The pyridazinone compound according to (iv) or a salt thereof. (23) The pyridazinone compound according to (22) or a salt thereof, wherein d is 1 or 2. (24) A pyridazinone compound according to (22) or a salt thereof, wherein Y and R Ａ are 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 (25) The pyridazinone compound or salt thereof according to any one of (1) to (23), wherein R is haloalkoxy. １ , R ２ , R ３ and R ４ are 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 or (C １ -C ４ (26) The pyridazinone compound or a salt thereof according to any one of (1) to (24), wherein R is alkylsulfinyl. １ , R ２ , R ３ and R ４ are halogen, (C １ -C ４ ) alkyl or (C １ -C ４ (27) The pyridazinone compound or a salt thereof according to any one of (1) to (24), wherein G is R Ｄ (C １ -C ４ ) alkyl, —C(═O)E or alkylsulfonyl; R Ｄ (C １ -C ４ ) alkoxy, cyano, (C １ -C ４ ) alkoxycarbonyl or (C １ -C ４ ) alkoxycarbonyloxy; E is (C １ -C ８ ) alkyl, (C ２ -C ８ ) alkenyl, (C ３ -C ６ ) cycloalkyl, heterocycloalkyl, (C １ -C ８ ) haloalkyl, (C １ -C ４ ) dialkylamino, N—(C １ -C ４ ) alkoxy-N—(C １ -C ４ ) alkylamino, V Ａ phenyl optionally substituted with V Ａ pyridyl optionally substituted with (C ３ -C ６ ) cycloalkyl (C １ -C ４ ) alkyl, heterocycloalkyl (C１ -C ４ ) alkyl, (C １ -C ４ ) alkoxy(C １ -C ３ ) alkyl, (C １ -C ４ ) alkylthio (C １ -C ３ ) alkyl, V Ａ phenyl (C １ -C ４ ) alkyl, V Ａ phenyloxy (C １ -C ３ ) alkyl, V Ａ phenyl (C ２ -C ４ ) alkenyl, (C １ -C ７ ) alkoxy, (C ２ -C ７ ) alkenyloxy, (C ２ -C ７ ) alkynyloxy, (C ３ -C ６ ) cycloalkyloxy, (C １ -C ７ ) haloalkoxy, (C １ -C ４ ) alkoxy(C １ -C ３ ) Alkoxy, V Ａ phenyloxy optionally substituted with V Ａ naphthyloxy optionally substituted by V Ｂ phenyl (C １ -C ３ ) alkoxy, (C １ -C ７ (28) The pyridazinone compound or a salt thereof according to any one of (1) to (26), wherein G is -C(=O)E; １ -C ８ ) alkyl, (C ２ -C ８ ) alkenyl, (C ３ -C ６ ) cycloalkyl, heterocycloalkyl, (C１ -C ８ ) haloalkyl, (C １ -C ４ ) dialkylamino, N—(C １ -C ４ ) alkoxy-N—(C １ -C ４ ) alkylamino, V Ａ phenyl optionally substituted with V Ａ pyridyl optionally substituted with (C ３ -C ６ ) cycloalkyl (C １ -C ４ ) alkyl, heterocycloalkyl (C １ -C ４ ) alkyl, (C １ -C ４ ) alkoxy(C １ -C ３ ) alkyl, (C １ -C ４ ) alkylthio (C １ -C ３ ) alkyl, V Ａ phenyl (C １ -C ４ ) alkyl, V Ａ phenyloxy (C １ -C ３ ) alkyl, V Ａ phenyl (C ２ -C ４ ) alkenyl, (C １ -C ７ ) alkoxy, (C ２ -C ７ ) alkenyloxy, (C ２ -C ７ ) alkynyloxy, (C ３ -C ６ ) cycloalkyloxy, (C １ -C ７ ) haloalkoxy, (C １ -C ４ ) alkoxy(C １ -C ３ ) Alkoxy, V Ａ phenyloxy optionally substituted with V Ａnaphthyloxy optionally substituted by V Ｂ phenyl (C １ -C ３ ) alkoxy, (C １ -C ７ (29) The pyridazinone compound or a salt thereof according to any one of (1) to (26), wherein G is -C(=O)E; E is (C) alkylthio or 2-imidazolidinone, and the heterocycloalkyl and heterocycloalkyl moiety in E are each a 3- to 6-membered group containing, in addition to carbon atoms, one or more atoms of one or more kinds selected from oxygen atoms, nitrogen atoms, and sulfur atoms. １ -C ８ ) alkyl, (C ２ -C ８ ) alkenyl, (C ３ -C ６ ) cycloalkyl, heterocycloalkyl, (C １ -C ８ ) haloalkyl, (C １ -C ４ ) dialkylamino, N—(C １ -C ４ ) alkoxy-N—(C １ -C ４ ) alkylamino, V Ａ phenyl optionally substituted with V Ａ pyridyl optionally substituted with (C ３ -C ６ ) cycloalkyl (C １ -C ４ ) alkyl, V Ａ phenyl (C １ -C ４ ) alkyl, V Ａ phenyloxy (C １ -C ３ ) alkyl, V Ａ phenyl (C ２ -C ４ ) alkenyl, (C １ -C ７ ) alkoxy, (C ２ -C ７ ) alkenyloxy, (C ３ -C ６) cycloalkyloxy, (C １ -C ７ ) haloalkoxy, (C １ -C ４ ) alkoxy(C １ -C ３ ) Alkoxy, V Ａ phenyloxy or V optionally substituted Ｂ phenyl (C １ -C ３ (30) The pyridazinone compound or a salt thereof according to any one of (1) to (26), wherein G is -C(=O)E; E is (C)alkoxy, and the heterocycloalkyl and heterocycloalkyl moiety in E are each a 3- to 6-membered group containing, in addition to carbon atoms, one or more atoms selected from oxygen atoms, nitrogen atoms, and sulfur atoms. １ -C ７ ) alkoxy, (C ２ -C ７ ) alkenyloxy, (C ２ -C ７ ) alkynyloxy, (C ３ -C ６ ) cycloalkyloxy, (C １ -C ７ ) haloalkoxy, (C １ -C ４ ) alkoxy(C １ -C ３ ) alkoxy or V Ｂ phenyl (C １ -C ３ (31) The pyridazinone compound or a salt thereof according to any one of (1) to (26), wherein G is —C(═O)E; and E is (C １ -C ８ ) alkyl, (C ２ -C ８ ) alkenyl, (C ３ -C ６ ) cycloalkyl, heterocycloalkyl, (C １ -C ８ ) haloalkyl, V Ａ phenyl optionally substituted with V Ａ pyridyl optionally substituted with (C ３ -C６ ) cycloalkyl (C １ -C ４ ) alkyl, heterocycloalkyl (C １ -C ４ ) alkyl, (C １ -C ４ ) alkoxy(C １ -C ３ ) alkyl, (C １ -C ４ ) alkylthio (C １ -C ３ ) alkyl, V Ａ phenyl (C １ -C ４ ) alkyl, V Ａ phenyloxy (C １ -C ３ ) alkyl, V Ａ phenyl (C ２ -C ４ ) alkenyl, V Ａ phenyloxy or V optionally substituted Ａ (32) The pyridazinone compound or a salt thereof according to any one of (1) to (26), wherein G is -C(=O)E; and E is naphthyloxy optionally substituted by (C １ -C ８ ) alkyl, (C ２ -C ８ ) alkenyl, (C ３ -C ６ ) cycloalkyl, heterocycloalkyl, (C １ -C ８ ) haloalkyl, (C ３ -C ６ ) cycloalkyl (C １ -C ４ ) alkyl, heterocycloalkyl (C １ -C ４ ) alkyl, (C １ -C ４ ) alkoxy(C １ -C ３) alkyl, (C １ -C ４ ) alkylthio (C １ -C ３ ) alkyl, V Ａ phenyl (C １ -C ４ ) alkyl, V Ａ phenyloxy (C １ -C ３ ) alkyl or V Ａ phenyl (C ２ -C ４ (33) The pyridazinone compound or a salt thereof according to any one of (1) to (26), wherein G is -C(=O)E; E is (C)alkenyl, and the heterocycloalkyl and heterocycloalkyl moiety in E are each a 3- to 6-membered group containing, in addition to carbon atoms, one or more atoms of one or more kinds selected from oxygen atoms, nitrogen atoms, and sulfur atoms. １ -C ８ ) alkyl, (C ２ -C ８ ) alkenyl, (C ３ -C ６ ) cycloalkyl, (C １ -C ８ ) haloalkyl, (C １ -C ４ ) alkoxy(C １ -C ３ ) alkyl, (C １ -C ７ ) alkoxy, (C ２ -C ７ ) alkenyloxy, (C ３ -C ６ ) cycloalkyloxy, (C １ -C ７ ) haloalkoxy or (C １ -C ４ ) alkoxy(C １ -C ３ (34) The pyridazinone compound or a salt thereof according to any one of (1) to (26), wherein Z is (C ) alkoxy. １ -C ５ ) alkyl, (C ３ -C ６ ) cycloalkyl, (C１ -C ４ ) alkoxy(C １ -C ４ ) alkyl or (C １ -C ４ (35) The pyridazinone compound or a salt thereof according to any one of (1) to (33), wherein Z is (C ) haloalkyl. １ -C ５ ) alkyl or (C ３ -C ６ (36) A pyridazinone compound or a salt thereof according to any one of (1) to (35), wherein n is 1 or 2. (37) A pyridazinone compound or a salt thereof according to any one of (1) to (35), wherein n is 2. (38) A pyridazinone compound or a salt thereof, which has at least Y bonded to the para position of the pyridazinone ring, and this Y is selected from the group consisting of halogen, (C １ -C ４ ) haloalkyl, (C １ -C ４ ) haloalkoxy, (C １ -C ４ ) alkylthio, (C １ -C ４ ) alkylsulfinyl, (C １ -C ４ (39) A pyridazinone compound or a salt thereof according to any one of (1) to (37), which is selected from the group consisting of a halogen atom, a methyl group ... １ -C ４ ) haloalkyl or (C １ -C ４ (40) A pyridazinone compound or a salt thereof according to any one of (1) to (37), which has at least Y bonded to the para position of the pyridazinone ring, and this Y is a halogen. (41) A pyridazinone compound or a salt thereof according to any one of (1) to (37), which has at least Y bonded to the para position of the pyridazinone ring, and this Y is (C １ -C ４(42) A pyridazinone compound or a salt thereof according to any one of (1) to (37), which has at least Y bonded to the para position of the pyridazinone ring, and this Y is (C １ -C ４ (43) The pyridazinone compound or a salt thereof according to any one of (1) to (37), wherein Y and / or R are at the ortho position relative to the pyridazinone ring. Ａ and the ortho-substituted group has at least one substituent attached as １ -C ４ ) alkyl, (C ２ -C ４ ) alkenyl, (C ２ -C ４ ) alkynyl, (C ３ -C ６ ) cycloalkyl, (C １ -C ４ ) alkoxy or —C(═O)R Ｂ and R Ｂ (C １ -C ４ (44) A pyridazinone compound or a salt thereof according to any one of (1) to (42), wherein Y and / or R are at the ortho position relative to the pyridazinone ring. Ａ and the ortho-substituted group has at least one substituent attached as a halogen or (C １ -C ４ (45) The pyridazinone compound or a salt thereof according to any one of (1) to (42), wherein X is C(R Ａ (46) The pyridazinone compound or salt thereof according to any one of (1) to (6) and (13) to (44), wherein X is C(R Ａ ) or N, n is 2, and these two Ys are substituted at the para-position and the ortho-position with respect to the pyridazinone ring.

[0265] (47) A pest control agent containing the compound or salt thereof according to any one of (1) to (46) as an active ingredient. (48) An insecticide, acaricide, nematicide, or soil pesticide containing the compound or salt thereof according to any one of (1) to (46) as an active ingredient. (49) An insecticide containing the compound or salt thereof according to any one of (1) to (46) as an active ingredient. (50) A method for controlling pests by applying an effective amount of the compound or salt thereof according to any one of (1) to (46).

[0266] Examples of the present invention will be described below, but the present invention is not limited to these. First, synthesis examples of the compounds of the present invention will be described.

[0267] Synthesis Example 1 Synthesis of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-6-ethyl-5-methoxycarbonyloxy-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridazin-3(2H)-one (Compound No. 1-111 described below) (1) A mixture of 6-bromo-4,5-dichloropyridazin-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 reacted with stirring at 80°C for 16 hours while heating. After the reaction, the mixture was allowed to cool to room temperature, and a saturated aqueous solution of sodium bicarbonate was added. The resulting mixture was extracted with ethyl acetate, and the combined organic extracts were 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 / heptane) to obtain 19.1 g (yield 75%) of 6-bromo-4,5-dichloro-2-(tetrahydro-2H-pyran-2-yl)pyridazin-3(2H)-one. 1 The H-NMR spectrum data is as follows: 1 H-NMR (CDCl3, 500MHz): 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)pyridazin-3(2H)-one (2.0 g, 6.1 mmol), ethylboronic acid (0.54 g, 7.3 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride dichloromethane adduct (0.50 g, 0.61 mmol), cesium carbonate (2.3 g, 7.0 mmol), and 1,4-dioxane (18 mL) was stirred under reflux under a nitrogen atmosphere for 16 hours. After the reaction, the mixture was cooled on ice and water was added. The resulting mixture was extracted with ethyl acetate, and the combined organic extracts were 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 / heptane) to obtain 1.1 g (yield 62%) of 4,5-dichloro-6-ethyl-2-(tetrahydro-2H-pyran-2-yl)pyridazin-3(2H)-one. 1 The H-NMR spectrum data is as follows: 1 H-NMR (CDCl3, 500MHz): 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)pyridazin-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 heated to 80°C and reacted with stirring for 2 hours. After the reaction, the mixture was allowed to cool to room temperature and then concentrated. Ethanol was added to the resulting residue and azeotropically dehydrated under reduced pressure to obtain 2.3 g (yield 85%) of 4,5-dichloro-6-ethylpyridazin-3(2H)-one. 1 The H-NMR spectrum data is as follows: 1H-NMR (CDCl3, 500MHz): 10.47 (1H, brs), 2.80 (2H, q), 1.26 (3H, t)

[0270] (4) To a solution of 4,5-dichloro-6-ethylpyridazin-3(2H)-one (2.2 g, 11 mmol) in N,N-dimethylformamide (20 mL) was added sodium hydride (dispersed in approximately 60% liquid paraffin) (0.53 g, 13 mmol) in small portions 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. After the reaction, water was added. The resulting mixture was extracted with ethyl acetate, and the combined organic extracts were 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 / heptane) to obtain 2.9 g (70% yield) of 4,5-dichloro-2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-6-ethylpyridazin-3(2H)-one. This thing 1 The H-NMR spectrum data is as follows: 1 H-NMR (CDCl3, 500MHz): 8.81 (1H, d), 8.18 (1H, d), 2.87 (2H, q), 1.27 (3H, t)

[0271] (5) To a solution of 3-(trifluoromethyl)pyrazole (1.5 g, 11 mmol) in N,N-dimethylformamide (21 mL) was added sodium hydride (dispersed in approximately 60% liquid paraffin) (0.45 g, 11 mmol) in small portions at 0°C. After stirring at 0°C for 30 minutes, 4,5-dichloro-2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-6-ethylpyridazin-3(2H)-one (2.0 g, 5.4 mmol) was added. The mixture was then reacted at 60°C for 2 hours with stirring. After the reaction, the mixture was allowed to cool to room temperature, and 1N aqueous sodium hydroxide solution (7 mL, 7 mmol) was added to the resulting reaction mixture, followed by stirring at 60°C for 1 hour. After the reaction, the mixture was allowed to cool to room temperature, and 1N hydrochloric acid was added to adjust the solution to acidity. The resulting mixture was extracted with ethyl acetate, and the combined organic extracts were 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 / heptane) to obtain 1.4 g (yield 57%) of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-6-ethyl-5-hydroxy-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridazin-3(2H)-one. 1 The H-NMR spectrum data is as follows: 1 H-NMR (CDCl3, 300MHz): 12.98 (1H, s), 9.33 (1H, dd), 8.84 (1H, dd), 8.20 (1H, dd), 6.78 (1H, dd), 2.88 (2H, q), 1.31 (3H, t)

[0272] (6) 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-6-ethyl-5-hydroxy-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridazin-3(2H)-one (0.15 g, 0.33 mmol) and triethylamine (0.23 mL, 1.65 mmol) were dissolved in tetrahydrofuran (2 mL), and methyl chloroformate (94 mg, 0.99 mmol) was added. The mixture was then stirred at room temperature for 3 hours. After dilution with ethyl acetate, water was added. The resulting mixture was extracted with ethyl acetate. The combined 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 / heptane) to obtain 0.15 g of the target compound (yield: 91%).

[0273] Synthesis Example 2 Synthesis of 5-acetoxy-2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-6-ethyl-4-(4-fluoro-1H-pyrazol-1-yl)pyridazin-3(2H)-one (Compound No. 1-58 described below) (1) To a solution of sodium hydroxide (2.79 g, 69.7 mmol) in water (20 mL), 4-fluoro-1H-pyrazole (2.00 g, 23.3 mmol) and bromoacetic acid (4.84 g, 34.9 mmol) were added in this order. The mixture was then heated to 100°C for 15 hours while stirring, and the reaction was carried out. After the reaction, the mixture was cooled to 0°C, and 2N hydrochloric acid was added to adjust the solution to acidity. The mixture was diluted with ethyl acetate, and then water was added. The resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give 2.08 g (62% yield) of crude 2-(4-fluoro-1H-pyrazol-1-yl)acetic acid. 1 The H-NMR spectrum data is as follows: 1 H-NMR (CDCl3, 500MHz): 7.43 (1H, d), 7.37 (1H, d), 4.88 (2H, s)

[0274] (2) To a solution of 2,6-dimethyl-4-(trifluoromethyl)aniline (2.49 g, 13.16 mmol) in concentrated hydrochloric acid (12 mL), a solution of sodium nitrite (1.10 g, 15.94 mmol) in water (12 mL) was added at 0°C, and the mixture was stirred at the same temperature for 1 hour to prepare an aqueous diazonium salt solution. Separately, tin(II) chloride dihydrate (8.91 g, 15.5 mmol) was dissolved in concentrated hydrochloric acid (28 mL), and the above-mentioned aqueous diazonium salt solution was added dropwise at room temperature. After the dropwise addition, the mixture was allowed to react at room temperature for 16 hours with stirring. After the reaction, heptane was added and the mixture was filtered. Ethanol was added to the resulting solid and azeotropically dehydrated under reduced pressure to obtain 2.84 g (90% yield) of the crude product [2,6-dimethyl-4-(trifluoromethyl)phenyl]hydrazine hydrochloride. Of this product, 1 The H-NMR spectrum data is as follows: 1 H-NMR (DMSO-d6, 500 MHz): 9.77 (3H, br), 7.46 (2H, s), 6.96 (1H, br), 2.43 (6H, s)

[0275] (3) [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 the (Boc) ２ 0 (3.63 g, 16.62 mmol) was added. Then, the mixture was allowed to react at room temperature for 12 hours with stirring. After the reaction, 2,2,2-trifluoroethanol (0.83 g, 8.31 mmol) and 4-dimethylaminopyridine (0.10 g, 0.83 mmol) were added. The mixture was allowed to react at room temperature for 1 hour with stirring. 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 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 / heptane) to obtain 1.76 g (yield 70%) of tert-butyl 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]hydrazine-1-formate. 1The H-NMR spectrum data is as follows: 1 H-NMR (CDCl3, 500MHz): 7.22 (2H, s), 6.34 (1H, br), 5.83 (1H, d), 2.40 (6H, s), 1.40 (9H, brs)

[0276] (4) 2-(4-Fluoro-1H-pyrazol-1-yl)acetic acid (0.11 g, 0.79 mmol) and N,N-dimethylformamide (10 mg, 0.14 mmol) were dissolved in dichloromethane (3 mL), oxalyl chloride (0.12 g, 0.92 mmol) was added, and the reaction was carried out at room temperature with stirring for 2 hours. After the reaction, the mixture was concentrated under reduced pressure to obtain the acid chloride. Separately, potassium carbonate (0.18 g, 1.31 mmol) was added to a dichloromethane (3 mL) solution of tert-butyl 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]hydrazine-1-formate (0.20 g, 0.66 mmol). A dichloromethane (2 mL) solution of the acid chloride described above was added dropwise at 0°C. After the dropwise addition, the reaction was carried out at room temperature with stirring for 3 hours. After the reaction, ethyl acetate and water were added, and the resulting mixture was extracted with ethyl acetate. The combined 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 / heptane) to obtain 0.21 g (74% yield) of tert-butyl 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-2-[2-(4-fluoro-1H-pyrazol-1-yl)acetyl]hydrazine-1-formate. 1 The H-NMR spectrum data is as follows: 1 H-NMR (CDCl3, 300MHz): 7.58 (1H, brs), 7.32-7.52 (7.48H, m), 6.78 (0.87H, brs), 5.11 (2H, brs), 4.53 (1.74H, s), 2.52 (5.22H, s), 2.38 (6H, brs), 1.39-1.55 (16.83H, m)

[0277] (5) To a dichloromethane (3 mL) solution of tert-butyl 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-2-[2-(4-fluoro-1H-pyrazol-1-yl)acetyl]hydrazine-1-formate (0.21 g, 0.49 mmol), trifluoroacetic acid (0.50 mL) was added and the mixture was stirred at room temperature for 3 hours. After the reaction, saturated aqueous sodium bicarbonate solution was added, and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. To the resulting residue, p-toluenesulfonic acid monohydrate (10 mg, 0.08 mmol), methanol (5 mL), and methyl 2-oxobutyrate (50 mg, 0.47 mmol) were added in this order, and the mixture was stirred at 70°C for 2 hours. After the reaction, the mixture was allowed to cool to room temperature and then concentrated. The mixture was diluted with ethyl acetate and then water was added. The resulting mixture was extracted with ethyl acetate, and the combined 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 / heptane) to obtain 0.14 g (yield 83%) of methyl 2-{2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-2-[2-(4-fluoro-1H-pyrazol-1-yl)acetyl]hydrazinylidene}butyrate. 1 The H-NMR spectrum data is as follows: 1 H-NMR (CDCl3, 300MHz): 7.39-7.51 (3.28H, m), 7.35 (2H, s), 5.54 (0.64H, s), 5.52 (2H, s), 3.91 (0.96H, s), 3.11 (3H, s), 2.50 (2H, q), 2.21 (1.92H, s), 2.18 (6H, s), 1.90 (0.64H, q), 1.28 (0.96H, t), 1.22 (3H, t)

[0278] (6) 1,8-diazabicyclo[5.4.0]-7-undecene (0.15 mL, 0.98 mmol) was added to a solution of methyl 2-{2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-2-[2-(4-fluoro-1H-pyrazol-1-yl)acetyl]hydrazinylidene}butyrate (0.14 g, 0.33 mmol) in acetonitrile (4 mL), and the mixture was stirred at 70°C for 2 hours. After the reaction, the mixture was allowed to cool to room temperature, and then ethyl acetate and water were added. 1N hydrochloric acid was added to adjust the solution to acidity, and the resulting mixture was extracted with ethyl acetate. The combined 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 / heptane) to obtain 0.11 g (yield 85%) of 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-6-ethyl-4-(4-fluoro-1H-pyrazol-1-yl)-5-hydroxypyridazin-3(2H)-one. 1 The H-NMR spectrum data is as follows: 1 H-NMR (CDCl3, 500MHz): 13.55 (1H, s), 9.21 (1H, d), 7.66 (1H, d), 7.46 (2H, s), 2.84 (2H, q), 2.16 (6H, s), 1.27 (3H, t)

[0279] (7) 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-6-ethyl-4-(4-fluoro-1H-pyrazol-1-yl)-5-hydroxypyridazin-3(2H)-one (50 mg, 0.13 mmol) and triethylamine (64 mg, 0.63 mmol) were dissolved in tetrahydrofuran (4 mL), and acetyl chloride (30 mg, 0.38 mmol) was added. The mixture was then stirred at room temperature for 3 hours. After dilution with ethyl acetate, water was added. The resulting mixture was extracted with ethyl acetate. The combined 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 / heptane) to obtain 45 mg of the target compound (yield 81%).

[0280] Synthesis Example 3: Alternative Method for 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-6-ethyl-5-methoxycarbonyloxy-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridazin-3(2H)-one (Compound No. 1-111 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 this order. The mixture was then reacted with stirring at 100°C for 15 hours while being heated. After the reaction, the mixture was cooled to 0°C, and then 2N hydrochloric acid was added to adjust the solution to be acidic, followed by the addition of heptane. The precipitated solid was collected by filtration to obtain 3.41 g (yield 80%) of the crude product, 2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid. 1 The H-NMR spectrum data is as follows: 1 H-NMR (CDCl3, 500MHz): 7.55 (1H, d), 6.62 (1H, d), 5.04 (2H, s)

[0281] (2) A mixture of 3-chloro-2-hydrazinyl-5-(trifluoromethyl)pyridine (0.67 g, 3.15 mmol), methyl 2-oxobutyrate (0.44 g, 3.78 mmol), and ethanol (10 mL) was reacted with stirring at 60°C for 15 hours while heating. After the reaction, the mixture was concentrated to obtain a residue. After dilution with ethyl acetate, water was added. The resulting mixture was extracted with ethyl acetate, and 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 / heptane) to obtain 0.79 g (yield 81%) of methyl 2-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]hydrazinylidene}butyrate. 1 The H-NMR spectrum data is as follows: 1H-NMR (CDCl3, 500MHz): 8.54 (1H, s), 7.82 (1H, s), 3.91 (3H, s), 2.69 (2H, q), 1.20 (3H, t)

[0282] (3) A mixture of 2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid (308 mg, 1.59 mmol), N,N-dimethylformamide (5 mg, 0.070 mmol), and dichloromethane (8 mL) was stirred in an ice bath for several minutes, and then oxalyl chloride (0.15 mL, 1.74 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 acid chloride. Separately, under a nitrogen atmosphere, a tetrahydrofuran solution of lithium hexamethyldisilazide (1.04 mL, 1.3 molar, 1.36 mmol) was added to a tetrahydrofuran (8 mL) solution of methyl 2-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]hydrazinylidene}butyrate (420 mg, 1.36 mmol) in an ice bath. After stirring in the ice bath for 1 hour, the aforementioned acid chloride was added. The mixture was then allowed to react at room temperature for 18 hours with stirring. After dilution with ethyl acetate, water was added. The resulting mixture was extracted with ethyl acetate, and 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 / heptane) to obtain 0.12 g (yield 20%) of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-6-ethyl-5-hydroxy-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridazin-3(2H)-one. 1 The H-NMR spectrum data is as follows: 1 H-NMR (CDCl3, 300MHz): 12.98 (1H, s), 9.33 (1H, dd), 8.84 (1H, dd), 8.19 (1H, dd), 6.78 (1H, dd), 2.88 (2H, q), 1.31 (3H, t)

[0283] (4) In accordance with the description of (6) of Synthesis Example 1, the target product, 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-6-ethyl-5-methoxycarbonyloxy-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridazin-3(2H)-one, was synthesized from 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-6-ethyl-5-hydroxy-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridazin-3(2H)-one.

[0284] Synthesis Example 4 Synthesis of 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-5-isobutyryloxy-4-(3-methyl-1H-pyrazol-1-yl)-6-(trifluoromethyl)pyridazin-3(2H)-one (Compound No. 1-182 shown below) (1) 4-(3-bromo-1H-pyrazol-1-yl)-2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-5-hydroxy-6-(trifluoromethyl)pyridazin-3(2H)-one (81 mg, 0.16 mmol), trimethylboroxine (0.11 mL, 0.81 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride dichloromethane adduct (13 mg, 0.020 mmol), and potassium carbonate (68 mg, 0.49 mmol), prepared in accordance with the description of Synthesis Example 2 (1) to (6), were dissolved in water (2 mL) and 1,4-dioxane (4 mL). The mixture was reacted with stirring at 140°C for 6 hours while being heated in a microwave synthesizer. After the reaction, the mixture was allowed to cool to room temperature. Water and 1N hydrochloric acid were added, followed by ethyl acetate, and the mixture was filtered through Celite. The resulting filtrate mixture was extracted with ethyl acetate. The combined 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 / heptane) to obtain 46 mg (yield 65%) of 2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-5-hydroxy-4-(3-methyl-1H-pyrazol-1-yl)-6-(trifluoromethyl)pyridazin-3(2H)-one. 1The H-NMR spectrum data is as follows: 1 H-NMR (CDCl3, 300MHz): 8.93 (1H, d), 7.32 (2H, s), 6.18 (1H, d), 2.28 (3H, s), 2.01 (6H, s)

[0285] (2) 2-[2,6-Dimethyl-4-(trifluoromethyl)phenyl]-5-hydroxy-4-(3-methyl-1H-pyrazol-1-yl)-6-(trifluoromethyl)pyridazin-3(2H)-one (25 mg, 0.060 mmol) and triethylamine (8.8 mg, 0.090 mmol) were dissolved in tetrahydrofuran (1 mL), and isobutyryl chloride (8.6 mg, 0.080 mmol) was added. The mixture was then stirred at room temperature for 12 hours. After dilution with ethyl acetate, water was added. The resulting mixture was extracted with ethyl acetate. The combined 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 / heptane) to obtain 10 mg of the target compound (yield: 34%).

[0286] Synthesis Example 5 Synthesis of 4-[5-(4-chloro-1H-pyrazol-1-yl)-3-ethyl-4-isobutyryloxy-6-oxopyridazin-1(6H)-yl]-3,5-dimethylbenzonitrile (Compound No. 1-110 described below) (1) A mixture of methyl 4-[5-(4-chloro-1H-pyrazol-1-yl)-3-ethyl-4-hydroxy-6-oxopyridazin-1(6H)-yl]-3,5-dimethylbenzoate (0.15 g, 0.37 mmol), prepared in accordance with the description in Synthesis Example 2 (1) to (6), lithium aluminum hydride (42 mg, 1.10 mmol), and tetrahydrofuran (5 mL) was reacted at 0° C. for 3 hours with stirring. After the reaction, 2N hydrochloric acid was added at 0° C. After filtration through Celite, the filtrate was diluted with ethyl acetate, and water was added. The resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered through a funnel packed with silica gel, and concentrated to give 93 mg of crude product, 4-(4-chloro-1H-pyrazol-1-yl)-6-ethyl-5-hydroxy-2-[4-(hydroxymethyl)-2,6-dimethylphenyl]pyridazin-3(2H)-one. 1 The H-NMR spectrum data is as follows: 1 H-NMR (CDCl3, 300MHz): 13.34 (1H, brs), 9.36 (1H, s), 7.72 (1H, s), 7.22 (2H, s), 4.71 (2H, s), 2.86 (2H, q), 2.12 (6H, s), 1.29 (3H, t)

[0287] (2) Activated manganese dioxide (0.65 g, 7.44 mmol) was added to a dichloromethane (5 mL) solution of 4-(4-chloro-1H-pyrazol-1-yl)-6-ethyl-5-hydroxy-2-[4-(hydroxymethyl)-2,6-dimethylphenyl]pyridazin-3(2H)-one (93 mg, 0.25 mmol), and the mixture was stirred at room temperature for 15 hours. After filtering through Celite, the obtained filtrate was concentrated to obtain 82 mg of the crude product, 4-[5-(4-chloro-1H-pyrazol-1-yl)-3-ethyl-4-hydroxy-6-oxopyridazin-1(6H)-yl]-3,5-dimethylbenzaldehyde. 1 The H-NMR spectrum data is as follows: 1 H-NMR (CDCl3, 300MHz): 13.45 (1H, brs), 10.04 (1H, s), 9.32 (1H, s), 7.74-7.75 (3H, m), 2.88 (2H, q), 2.20 (6H, s), 1.29 (3H, t)

[0288] (3) 4-[5-(4-chloro-1H-pyrazol-1-yl)-3-ethyl-4-hydroxy-6-oxopyridazin-1(6H)-yl]-3,5-dimethylbenzaldehyde (82 mg, 0.22 mmol) and sodium acetate (18 mg, 0.22 mmol) were dissolved in ethanol (3 mL), and hydroxylamine (50% aqueous solution) (73 mg, 1.10 mmol) was added. The mixture was then stirred at room temperature for 15 hours. After the reaction, 2N hydrochloric acid (5 mL) was added. The mixture was diluted with ethyl acetate and then water was added. The resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give 86 mg of crude product, (E)-4-[5-(4-chloro-1H-pyrazol-1-yl)-3-ethyl-4-hydroxy-6-oxopyridazin-1(6H)-yl]-3,5-dimethylbenzaldoxime. 1 The H-NMR spectrum data is as follows: 1H-NMR (CDCl3, 300MHz): 13.45 (1H, brs), 9.35 (1H, s), 8.13 (1H, s), 7.73 (1H, s), 7.43 (2H, s), 2.86 (2H, q), 2.13 (6H, s), 1.30 (3H, t)

[0289] (4) A mixture of (E)-4-[5-(4-chloro-1H-pyrazol-1-yl)-3-ethyl-4-hydroxy-6-oxopyridazin-1(6H)-yl]-3,5-dimethylbenzaldoxime (86 mg, 0.22 mmol) and acetic anhydride (5 mL) was heated to 140°C and reacted with stirring for 13 hours. After stirring, the mixture was concentrated to obtain a mixture. To a solution of this mixture in tetrahydrofuran (2 mL), 2N aqueous sodium hydroxide solution (7 mL) was added, and the mixture was reacted with stirring at room temperature for 2 hours. 2N hydrochloric acid was added to adjust the acidity, and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a mixture containing the target product. To a solution of this mixture in tetrahydrofuran (2 mL), 2N aqueous sodium hydroxide solution (2 mL) was added, and the mixture was reacted with stirring at room temperature for 1 hour. 2N hydrochloric acid was added to adjust the acidity, and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give 43 mg (52% yield) of 4-[5-(4-chloro-1H-pyrazol-1-yl)-3-ethyl-4-hydroxy-6-oxopyridazin-1(6H)-yl]-3,5-dimethylbenzonitrile. 1 The H-NMR spectrum data is as follows: 1 H-NMR (CDCl3, 300MHz): 13.47 (1H, brs), 9.30 (1H, s), 7.74 (1H, s), 7.52 (2H, s), 2.86 (2H, q), 2.15 (6H, s), 1.28 (3H, t)

[0290] (5) 4-[5-(4-chloro-1H-pyrazol-1-yl)-3-ethyl-4-hydroxy-6-oxopyridazin-1(6H)-yl]-3,5-dimethylbenzonitrile (20 mg, 0.050 mmol) and diisopropylethylamine (10 mg, 0.080 mmol) were dissolved in tetrahydrofuran (2 mL), and isobutyryl chloride (7 mg, 0.060 mmol) was added. The mixture was then stirred at room temperature for 3 hours. After dilution with ethyl acetate, water was added. The resulting mixture was extracted with ethyl acetate. The combined 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 / heptane) to obtain 19 mg of the target compound (yield: 80%).

[0291] Synthesis Example 6 Synthesis of 4-(3-chloro-1H-pyrazol-1-yl)-2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-5-isobutyryloxy-6-(methoxymethyl)pyridazin-3(2H)-one (Compound No. 1-230 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-dihydropyridazine-3-carboxylate (0.40 g, 0.88 mmol), prepared in accordance with the description in Synthesis Example 2 (1) to (6), lithium aluminum hydride (0.10 g, 2.63 mmol), and tetrahydrofuran (18 mL) was reacted with stirring at 0° C. 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 combined aqueous layers were acidified with 2N hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give 0.35 g of crude product, 4-(3-chloro-1H-pyrazol-1-yl)-2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-5-hydroxy-6-(hydroxymethyl)pyridazin-3(2H)-one. 1 The H-NMR spectrum data is as follows: 1H-NMR (CDCl3, 300MHz): 13.06 (1H, brs), 9.23 (1H, d), 7.49 (2H, s), 6.48 (1H, d), 4.85 (2H, s), 2.18 (6H, s)

[0292] (2) To a solution of 4-(3-chloro-1H-pyrazol-1-yl)-2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-5-hydroxy-6-(hydroxymethyl)pyridazin-3(2H)-one (0.27 g, 0.66 mmol) in N,N-dimethylformamide (4 mL) was added sodium hydride (dispersed in approximately 60% liquid paraffin) (0.10 g, 2.62 mmol) and methyl iodide (0.37 g, 2.62 mmol) at 0°C. The mixture was then reacted at room temperature for 15 hours with stirring. To the resulting reaction mixture was added 2N aqueous sodium hydroxide solution, and the mixture was then reacted at room temperature with stirring for 1 hour. After dilution with ethyl acetate, 0.5N hydrochloric acid was added. The resulting mixture was extracted with ethyl acetate. The combined 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 / heptane) to obtain 87 mg (yield 31%) of 4-(3-chloro-1H-pyrazol-1-yl)-2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-5-hydroxy-6-(methoxymethyl)pyridazin-3(2H)-one. 1 The H-NMR spectrum data is as follows: 1 H-NMR (CDCl3, 300MHz): 13.01 (1H, brs), 9.22 (1H, d), 7.48 (2H, s), 6.47 (1H, d), 4.61 (2H, s), 3.49 (3H, s), 2.18 (6H, s)

[0293] (3) 4-(3-chloro-1H-pyrazol-1-yl)-2-[2,6-dimethyl-4-(trifluoromethyl)phenyl]-5-hydroxy-6-(methoxymethyl)pyridazin-3(2H)-one (50 mg, 0.12 mmol) and triethylamine (15 mg, 0.15 mmol) were dissolved in tetrahydrofuran (2.5 mL), and isobutyryl chloride (15 mg, 0.14 mmol) was added. The mixture was then stirred at room temperature for 12 hours. After dilution with ethyl acetate, water was added. The resulting mixture was extracted with ethyl acetate. The combined 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 / heptane) to obtain 49 mg of the target compound (yield 84%).

[0294] Synthesis Example 7 Synthesis of 2-[2,6-dichloro-4-(methylsulfonyl)phenyl]-5-isobutyryloxy-6-isopropyl-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridazin-3(2H)-one (Compound No. 1-410 described below) (1) 2,6-Dichloroaniline (3.00 g, 18.5 mmol) was dissolved in dichloromethane (30 mL), and potassium peroxodisulfate (10.0 g, 37.0 mmol), ammonium thiocyanate (2.11 g, 27.8 mmol), and water (0.33 mL) were added. The mixture was then reacted at room temperature for 15 hours with stirring. The mixture was filtered using a funnel packed with Celite and silica gel, and the obtained filtrate was concentrated to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (eluent: ethyl acetate / heptane) to obtain 3.91 g (yield 96%) of 2,6-dichloro-4-thiocyanatoaniline. 1 The H-NMR spectrum data is as follows: 1 H-NMR(CDCl3, 300MHz): 7.45 (2H, s), 4.79 (2H, brs)

[0295] (2) 2,6-Dichloro-4-thiocyanatoaniline (4.03 g, 18.4 mmol) was dissolved in methanol (40 mL), and sodium methoxide (2.98 g, 55.2 mmol) was added. The mixture was then reacted at room temperature for 16 hours with stirring. After the reaction, the mixture was concentrated to obtain a residue. After dilution with ethyl acetate, water was added. The resulting mixture was extracted with ethyl acetate, and 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 / heptane) to obtain 1.75 g (yield 46%) of 2,6-dichloro-4-(methylthio)aniline. 1 The H-NMR spectrum data is as follows: 1 H-NMR(CDCl3, 300MHz): 7.26 (2H, s), 4.42 (2H, brs), 2.42 (3H, s)

[0296] (3) 2-[2,6-dichloro-4-(methylthio)phenyl]-5-isobutyryloxy-6-isopropyl-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridazin-3(2H)-one (Compound No. 1-408 described below) was synthesized from 2,6-dichloro-4-(methylthio)aniline in accordance with the description in Synthesis Example 2(2), Synthesis Example 3(2) to (3), and Synthesis Example 4(2).

[0297] (4) 2-[2,6-Dichloro-4-(methylthio)phenyl]-5-isobutyryloxy-6-isopropyl-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridazin-3(2H)-one (0.10 g, 0.18 mmol) was dissolved in ethyl acetate (4 mL), and 70% metachloroperbenzoic acid (wet product) (0.11 g, 0.46 mmol) was added. The mixture was then stirred at room temperature for 14 hours. After dilution with ethyl acetate, 1N aqueous sodium hydroxide solution and water were added. The resulting mixture was extracted with ethyl acetate. The combined 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 81 mg of the target compound (yield: 77%).

[0298] Next, representative examples of compounds of formula (I) are listed in Tables 1 and 2. These compounds can be synthesized based on the synthesis examples or the various production methods described above. General formula (I-1) in Table 1 represents compounds of formula (I) where Q is Q １ and a group of compounds in which Q is Q ３ In Table 1, W of general formula (I-1) Ａ If N is N, then Q is Q ３ otherwise, Q is Q １ In addition, general formula (I-2) in Table 2 corresponds to a group of compounds in which Q is Q ２ and a group of compounds in which Q is Q ４ In Table 2, W of general formula (I-2) Ｃ If N is N, then Q is Q ２ otherwise, Q is Q ４ The physical properties of representative examples of the compounds of formula (I) are shown in Tables 3 and 4. Table 3 shows the physical properties of representative examples of the compounds of formula (I). 1 The H-NMR spectrum data are shown in Table 3. 1In the H-NMR spectrum data, s is a singlet, brs is a broad singlet, d is a doublet, t is a triplet, q is a quartet, quin is a quintet, sext is a sextet, sep is a septet, m is a multiplet, and br is a broad line. Table 4 shows the melting points of representative examples of compounds of formula (I). In each table, No. indicates the compound number. The abbreviations used in Tables 1 and 2 represent the following substituents: Me is a methyl group, Et is an ethyl group, nPr is a normal propyl group, iPr is an isopropyl group, nBu is a normal butyl group, sBu is a secondary butyl group, tBu is a tertiary butyl group, cPr is a cyclopropyl group, cBu is a cyclobutyl group, cPen is a cyclopentyl group, cHex is a cyclohexyl group, DXAN is a 1,3-dioxan-2-yl group, and DXOL is a 1,3-dioxolan-2-yl group. In the tables, for example, "OMe" represents a methoxy group, "SMe" represents a methylthio group, and "OcPr" represents a cyclopropyloxy group. In Table 1, (R) A In the column, for example, "3-CF ３ The compound described as "is a compound in which the substitution position of "3" in the pyrazole ring given in the chemical structural formula in the table is CF ３ In Table 1, (R) represents a compound in which the 3-position of the pyrazole ring is substituted with one R, i.e., a compound in which "A=1". A In the column, compounds with "A=0" indicate that R is not substituted, and (Y) ｎ In the column, compounds with "n=0" indicate that Y is not substituted. In the columns for Z and G, * indicates the bonding position. Other similar descriptions in Tables 1 and 2 also follow this.

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[0359]

[0360] Test Example 1: Test of Efficacy Against Brown Planthoppers Rice seedlings were dipped into a chemical solution prepared so that the test compound had a concentration of 200 ppm or 50 ppm. After the chemical solution had air-dried, the roots were wrapped in wet absorbent cotton and placed in a test tube. Approximately 10 2nd- to 3rd-instar larvae of the brown planthopper were released into the tube, the opening of the tube was covered with gauze, and the tube was left to stand in a thermostatic chamber with lighting at 25°C. Five days after treatment, the number of dead or alive brown planthoppers was determined, and the mortality rate (%) was calculated using the following formula: [Calculation formula] Mortality rate (%) = (number of dead insects / number of released insects) x 100 As a result, the mortality rate of the above-mentioned compound No. 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33, 1-34, 1-35, 1-36, 1-37, 1-38, 1-39, 1-4 0, 1-41, 1-42, 1-43, 1-44, 1-45, 1-46, 1-47, 1-48, 1-49, 1-50, 1-51, 1-52, 1-53, 1-54, 1-55, 1-56, 1-57, 1-58, 1-59, 1-60, 1-61, 1-62, 1-63, 1-64, 1-65, 1-66, 1-67, 1-68, 1-69, 1-70, 1-71, 1-72, 1-73, 1-74, 1-75, 1-76, 1-77, 1- 78, 1-79, 1-80, 1-82, 1-83, 1-84, 1-85, 1-86, 1-87, 1-88, 1-89, 1-90, 1-91, 1-92, 1-93, 1-94, 1-95, 1-96, 1-97, 1-98, 1-99, 1-100, 1-101, 1-102, 1-103, 1-107, 1-108, 1-110, 1-111, 1-112, 1-113, 1-114, 1-115, 1-116, 1-117, 1- 118, 1-119, 1-120, 1-121, 1-123, 1-124, 1-125, 1-126, 1-127, 1-128, 1-131, 1-132, 1-133, 1-134, 1-135, 1-136, 1-137, 1-138, 1-140, 1-141, 1-142, 1-143, 1-144, 1-145, 1-146, 1-147, 1-148, 1-149, 1-150, 1-151, 1-152, 1-153,１－１５７、１－１５８、１－１５９、１－１６１、１－１６４、１－１６５、１－１６６、１－１７２、１－１７３、１－１７４、１－１７５、１－１７８、１－１８０、１－１８３、１－１８４、１－１８６、１－１８７、１－１８８、１－１８９、１－１９０、１－１９１、１－１９２、１－１９３、１－１９４、１－１９５、１－１９６、１－１９７、１－１９９、１－２０４、１－２０５、１－２０６、１－２０７、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、１－２２７、１－２２８、１－２３０、１－２３１、１－２３２、１－２３４、１－２４２、１－２４３、１－２５０、１－２６５、１－２７２、１－２８０、１－２８３、１－２８５、１－２８６、１－２８８、１－２９０、１－２９１、１－３０１、１－３０３、１－３０４、１－３０５、１－３０８、１－３０９、１－３１０、１－３１２、１－３１３、１－３１８、１－３２１、１－３２３、１－３２５、１－３２６、１－３２７、１－３２９、１－３３０、１－３３８、１－３３９、１－３４０、１－３４１、１－３４２、１－３４３、１－３４４、１－３４５、１－３４６、１－３４７、１－３４８、１－３４９、１－３５０、１－３５１、１－３５２、１－３５３、１－３５４、１－３５５、１－３５６、１－３５７、１－３５８、１－３５９、１－３６０、１－３６１、１－３６２、１－３６３、１－３６４、１－３６５、１－３６６、１－３６７、１－３６８、１－３６９、１－３７０、１－３７１、１－３７３、１－３７４、１－３７５、１－３７６、１－３７７、１－３７８、１－３７９、１－３８０、１－３８２、１－３８３、１－３８４、１－３８５、１－３８６、１－３８７、１－３８８、１－３８９、１－３９０、１－３９１、１－３９２、１－３９３、１－３９４、１－３９５、１－３９６、１－３９７、１－３９８、１－３９９、１－４００、１－４０１、１－４０２、１－４０４、１－４０７、１－４０９、１－４１２、１－４１４、１－４１５、１－４１６、１－４１８、１－４１９、１－４２０、１－４２１、１－４２２、１－４２３、１－４２４、１－４２５、１－４２６、１－４２７、１－４２８、１－４２９、１－４３０、１－４３１、1-433, 1-435, 1-436, 1-437, 1-438, 1-439, 1-440, 1-441, 1-442, 1-443, 1-444, 1-445, 1-446, 1-450, 1-451, 1-452, 1-455, 1-456, 1-457, 1-458, 1-459, 1-460, 1-461, 1-462, 1-463, 1-464, 1-465, 1-466, 1-467, 1-469, 1-470, 1-471, 1-474, 1-475, 1-476, 1-477, 1-478, 1-479, 1-480, 1-481, 1-482, 1-483, 1-485, 1-487, 1-488, 1-489, 1-490, 1-491, 1-492, 1-496, 1-498, 1-500, 1-504, 1-505, 1-506, 1-507, 1-508, 1-510, 1-511, 1-512, 1-513, 1-514, 1-515, 1-516, 1-517, 1-518, 1-521, 1-523, 1-524, 1-526, 1-527, 1-529, 1-531, 1-532, 1 -533, 1-534, 1-535, 1-536, 1-537, 1-538, 1-539, 1-541, 1-543, 1-544, 1-545, 1-546, 1-548, 1-550, 1-551, 1-552, 1-553, 1-554, 1-555, 1-557, 1-558, 1-563, 1-564, 1-569, 1-570, 1-571, 1-572, 1-573, 1-580, 1-581, 1-584, 1-586, 1-587, 1-588, 1-589, 1-590, 1-591, 1- Compounds No. 592, 1-596, 1-597, 1-598, 1-599, 1-600, 1-601, 1-602, 1-604, 1-605, 1-608, 1-609, 1-610, 1-611, 1-612, 1-613, 1-614, 1-615, 1-616, 1-617, 1-618, 1-619, 1-620, 1-621, 1-622, 1-623, 1-624, 1-625, 1-628, 1-629, 1-630, 1-631, 2-1 and 2-3 showed insect mortality of 80% or more at a concentration of 200 ppm. 1-104, 1-105, 1-106, 1-129, 1-155, 1-162, 1-168, 1-170, 1-171, 1-176, 1-177, 1-179, 1-181, 1-182, 1-208, 1-289,1-302, 1-319, 1-320, 1-322, 1-324, 1-381, 1-432, 1-453, 1-493, 1-495, 1-499, 1-509, 1-520, 1-603, 1-626 and 1-627 showed a mortality rate of 80% or more at a concentration of 50 ppm.

[0361] Test Example 2: Efficacy test against green peach aphids Five adult green peach aphids were released onto radish leaves placed in water in a test tube. After one day, the adults were removed, and the number of larvae parasitizing the radish leaves was counted as the number of test insects, which were then immersed in a chemical solution prepared so that the test compound had a concentration of 200 ppm or 50 ppm. After the chemical solution was air-dried, the test compound was left to stand in a thermostatic chamber with lighting at 25°C. Five days after treatment, the number of live and dead green peach aphids was determined, and the mortality rate (%) was calculated using the following formula. Note that detached insects and abnormal insects were considered to be dead insects. [Calculation formula] Mortality rate (%) = (number of dead insects / number of test insects) x 100 As a result, the above-mentioned Compound No. 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33, 1-34, 1-35, 1-36, 1-37, 1-38 , 1-39, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45, 1-46, 1-47, 1-48, 1-49, 1-50, 1-51, 1-52, 1-53, 1-54, 1-55, 1-56, 1-57, 1-58, 1-59, 1-60, 1-61, 1-62, 1-63, 1-64, 1-65, 1-66, 1-67, 1-68, 1-69, 1-70, 1-71, 1-72, 1-73, 1-74 , 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-81, 1-82, 1-83, 1-84, 1-85, 1-86, 1-87, 1-88, 1-89, 1-90, 1-91, 1-92, 1-93, 1-94, 1-95, 1-96, 1-97, 1-98, 1-99, 1-100, 1-101, 1-102, 1-103, 1-107, 1-108, 1-110, 1-111, 1-112, 1-113, 1-114, 1-117, 1-121, 1-123, 1-124, 1-125, 1-126, 1-127, 1-128, 1-131, 1-132, 1-133, 1-134, 1-135, 1-136, 1-137, 1-138, 1-139, 1-140, 1-141, 1-143, 1-144, 1-145, 1-146, 1-147, 1-148, 1-149, 1-150, 1-151,１－１５２、１－１５３、１－１５７、１－１５８、１－１５９、１－１６１、１－１６４、１－１６５、１－１６６、１－１７２、１－１７３、１－１７４、１－１７５、１－１７８、１－１８０、１－１８３、１－１８４、１－１８６、１－１８７、１－１８８、１－１８９、１－１９０、１－１９１、１－１９２、１－１９３、１－１９４、１－１９５、１－１９６、１－１９７、１－１９８、１－１９９、１－２０７、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、１－２２５、１－２２７、１－２２９、１－２３０、１－２３１、１－２３４、１－２４２、１－２４３、１－２５０、１－２６５、１－２７２、１－２７９、１－２８０、１－２８１、１－２８３、１－２８５、１－２８６、１－２８８、１－２９０、１－２９１、１－３０１、１－３０３、１－３０５、１－３０８、１－３０９、１－３１０、１－３１２、１－３１３、１－３１８、１－３２１、１－３２３、１－３２５、１－３２６、１－３２７、１－３２９、１－３３０、１－３３８、１－３３９、１－３４０、１－３４１、１－３４２、１－３４３、１－３４４、１－３４５、１－３４６、１－３４７、１－３４８、１－３４９、１－３５０、１－３５１、１－３５２、１－３５３、１－３５４、１－３５５、１－３５６、１－３５７、１－３５８、１－３５９、１－３６０、１－３６１、１－３６２、１－３６３、１－３６４、１－３６５、１－３６６、１－３６７、１－３６８、１－３６９、１－３７０、１－３７１、１－３７２、１－３７３、１－３７４、１－３７５、１－３７６、１－３７７、１－３７８、１－３８０、１－３８２、１－３８３、１－３８５、１－３８６、１－３８７、１－３８８、１－３８９、１－３９０、１－３９１、１－３９２、１－３９３、１－３９４、１－３９５、１－３９６、１－３９７、１－３９９、１－４０２、１－４０３、１－４０４、１－４０６、１－４０７、１－４０８、１－４０９、１－４１０、１－４１１、１－４１２、１－４１３、１－４１４、１－４１５、１－４１６、１－４１７、１－４１８、１－４１９、１－４２０、１－４２１、１－４２２、１－４２３、１－４２４、１－４２５、１－４２６、１－４２７、１－４２８、1-429, 1-430, 1-431, 1-433, 1-434, 1-435, 1-436, 1-437, 1-438, 1-439, 1-440, 1-441, 1-442, 1-443, 1-444, 1-447, 1-448, 1-452, 1-453, 1-454, 1-455, 1-456, 1-457, 1-458, 1-459, 1-460, 1-461, 1-462, 1-463, 1-464, 1-465, 1-466, 1-467, 1-468, 1-469, 1-470, 1-471, 1-472, 1-473, 1 -474, 1-475, 1-476, 1-477, 1-478, 1-479, 1-480, 1-481, 1-482, 1-483, 1-484, 1-485, 1-486, 1-487, 1-488, 1-489, 1-490, 1-491, 1-496, 1-498, 1-500, 1-504, 1-505, 1-506, 1-507, 1-508, 1-510, 1-511, 1-512, 1-513, 1-514, 1-515, 1-516, 1-517, 1-518, 1-519, 1-521, 1-523, 1-524, 1-5 26, 1-527, 1-529, 1-532, 1-533, 1-534, 1-535, 1-536, 1-537, 1-538, 1-539, 1-541, 1-543, 1-544, 1-545, 1-546, 1-547, 1-549, 1-550, 1-552, 1-553, 1-554, 1-555, 1-557, 1-558, 1-559, 1-561, 1-563, 1-564, 1-566, 1-569, 1-570, 1-571, 1-572, 1-573, 1-575, 1-580, 1-581, 1-582, 1-584 , 1-585, 1-586, 1-587, 1-588, 1-589, 1-592, 1-593, 1-594, 1-595, 1-596, 1-597, 1-598, 1-599, 1-600, 1-601, 1-602, 1-605, 1-607, 1-608, 1-610, 1-611, 1-612, 1-614, 1-615, 1-616, 1-617, 1-620, 1-621, 1-622, 1-623, 1-624, 1-628, 1-629, 1-630 and 1-631 showed insect mortality of 80% or more at a concentration of 200 ppm. 1-105, 1-106, 1-109, 1-129, 1-155, 1-162, 1-168,1-170, 1-176, 1-177, 1-179, 1-182, 1-208, 1-211, 1-289, 1-302, 1-319, 1-322, 1-324, 1-381, 1-432, 1-493, 1-495, 1-499, 1-509, 1-520, 1-603, 1-606, 1-626 and 1-627 showed a mortality rate of 80% or more at a concentration of 50 ppm.

[0362] Test Example 3: Efficacy test against two-spotted spider mites. Kidney bean leaves, on which about 20 adult two-spotted spider mites had been released in advance, were immersed in a chemical solution prepared so that the concentration of the test compound was 800 ppm, 200 ppm, or 50 ppm. After the chemical solution was air-dried, the leaves were left in a thermostatically-lit room at 25°C. Three days after treatment, the number of dead or alive two-spotted spider mites was determined, and the adult mortality rate (%) was calculated using the following formula. The detached adults and abnormal insects were considered to be dead insects.[Calculation formula] Adult insect mortality rate (%) = (number of dead insects / number of released insects) x 100 As a result, Compound No. 1-1, 1-2, 1-3, 1-5, 1-6, 1-7, 1-8, 1-9, 1-11, 1-13, 1-15, 1-16, 1-19, 1-20, 1-21, 1-22, 1-24, 1-27, 1-28, 1-29, 1-32, 1-34, 1-35, 1-36, 1-37, 1-38, 1-39, 1-40, 1-41, 1-43, 1-46, 1-47, 1-48, 1-49, 1-50, 1-51, 1-52, 1-53, 1-54, 1-55, 1-56, 1-57, 1-59, 1-60, 1-62 , 1-63, 1-64, 1-66, 1-67, 1-68, 1-69, 1-71, 1-72, 1-77, 1-79, 1-80, 1-82, 1-85, 1-86, 1-91, 1-92, 1-95, 1-96, 1-97, 1-102, 1-103, 1-107, 1-108, 1-124, 1-126, 1-131, 1-132, 1-133, 1-134, 1-135, 1-136, 1-137, 1-138, 1-140, 1-141, 1-144, 1-146, 1-151, 1-153, 1 -157, 1-172, 1-174, 1-178, 1-189, 1-199, 1-231, 1-243, 1-265, 1-283, 1-301, 1-303, 1-329, 1-343, 1-344, 1-345, 1-346, 1-347, 1-350, 1-353, 1-354, 1-355, 1-356, 1-357, 1-368, 1-369, 1-371, 1-378, 1-379, 1-380, 1-382, 1-388, 1-414, 1-415, 1-416, 1-418, 1 1-421, 1-424, 1-430, 1-435, 1-437, 1-449, 1-455, 1-456, 1-458, 1-460, 1-470, 1-474, 1-475, 1-476, 1-477, 1-478, 1-480, 1-481, 1-483, 1-485, 1-490, 1-500, 1-507, 1-529, 1-532, 1-535, 1-538, 1-543, 1-555, 1-563, 1-564 and 1-605 showed an adult insect mortality rate of 80% or more at a concentration of 200 ppm. 1-155, 1-176, 1-177, 1-179, 1-182, 1-302 and 1-381 showed a killing rate of 80% or more of adult insects at a concentration of 50 ppm.

[0363] Next, a comparative test will be described in which the effects of the compound of the present invention were compared with those of a comparative compound not having the specified diarylpyridazinone structure of the present invention.

[0364] Comparative Test Example 1 Rice seedlings were dipped into a chemical solution prepared so that the test compound had a concentration of 200 ppm or 50 ppm. After the chemical solution had air-dried, the roots were wrapped in wet absorbent cotton and placed in a test tube. Approximately 10 second- to third-instar larvae of the brown planthopper were released into the tube, and the tube opening was covered with gauze and allowed to stand in a lighted, thermostatic chamber at 25°C. Five days after treatment, the number of dead or alive brown planthoppers was determined, and the mortality rate (%) was calculated using the following formula: [Calculation formula] Mortality rate (%) = (number of dead insects / number of released insects) × 100 The test compound used was Compound No. 1-371 as the compound of the present invention, and the following comparative compound (A) was used as the comparative compound.

[0365]

[0366] The comparative results are shown in Table 5 below.

[0367]

[0368] Next, formulation examples are described.

[0369] Formulation Example 1 (1) Compound of the present invention 20 parts by weight (2) Clay 70 parts by weight (3) White carbon 5 parts by weight (4) Sodium polycarboxylate 3 parts by weight (5) Sodium alkylnaphthalenesulfonate 2 parts by weight The above ingredients are uniformly mixed to give a wettable powder.

[0370] Formulation Example 2 (1) Compound of the present invention 5 parts by weight (2) Talc 60 parts by weight (3) Calcium carbonate 34.5 parts by weight (4) Liquid paraffin 0.5 parts by weight The above ingredients are mixed uniformly to give a powder.

[0371] Formulation Example 3 (1) Compound of the present invention 20 parts by weight (2) N,N-dimethylacetamide 20 parts by weight (3) Polyoxyethylene tristyrylphenyl ether 10 parts by weight (4) Calcium dodecylbenzenesulfonate 2 parts by weight (5) Xylene 48 parts by weight The above ingredients are uniformly mixed and dissolved to prepare an emulsifiable concentrate.

[0372] Formulation Example 4 (1) Clay 68 parts by weight (2) Sodium lignin sulfonate 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) White carbon 25 parts by weight A mixture of the above components and the compound of the present invention are mixed in a weight ratio of 4:1 to prepare a wettable powder.

[0373] Formulation Example 5 (1) 50 parts by weight of the compound of the present invention (2) 2 parts by weight of formaldehyde condensate of sodium alkylnaphthalenesulfonate (3) 0.2 parts by weight of silicone oil (4) 47.8 parts by weight of water The above ingredients are uniformly mixed and pulverized to form a stock solution, to which are further added (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate, and the mixture is uniformly mixed, granulated, and dried to give a water dispersible granule.

[0374] Formulation Example 6 (1) Compound of the present invention 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene alkyl ether phosphate 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight (1) to (3) are uniformly mixed in advance, diluted with an appropriate amount of acetone, and then sprayed onto (4), and the acetone is removed to obtain granules.

[0375] Formulation Example 7 (1) Compound of the present invention 2.5 parts by weight (2) N,N-dimethylacetamide 2.5 parts by weight (3) Soybean oil 95.0 parts by weight The above ingredients are uniformly mixed and dissolved to give an ultra low volume formulation.

[0376] Formulation Example 8 (1) Compound of the present invention 10 parts by weight (2) Diethylene glycol monoethyl ether 80 parts by weight (3) Polyoxyethylene alkyl ether 10 parts by weight The above ingredients are mixed uniformly to obtain a liquid preparation.

[0377] The entire contents of the specification, claims and abstract of Japanese Patent Application No. 2023-166313 filed on September 27, 2023 are hereby incorporated by reference as the disclosure of the present invention.

Claims

1. Formula (I): (Wherein, Q is Q １ , Q ２ , Q ３ Or Q ４ : (In each formula, * indicates the bond position); X is CH, C(R Ａ ) or N; Y and R Ａ each represents a halogen, an alkyl, an alkenyl, an alkynyl, a cycloalkyl, a haloalkyl, an alkoxy, a haloalkoxy, an alkylthio, an alkylsulfinyl, an alkylsulfonyl, a cyano, or —C(═O)R Ｂ Z is alkyl, cycloalkyl, alkoxyalkyl, cycloalkylalkyl or haloalkyl; R １ , R ２ , R ３ and R ４ are each halogen, alkyl, cycloalkyl, haloalkyl, alkoxy, cycloalkyloxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, cyano, nitro, aldehyde, -CH(=NOR Ｃ ), 1,3-dioxan-2-yl or 1,3-dioxolan-2-yl; R Ｂ is a hydrogen atom or an alkyl group; R Ｃ is alkyl; n is an integer from 0 to 4; a is an integer from 0 to 3; b, c and d are each 0, 1 or 2; G is R Ｄ R is an alkyl group optionally substituted with -C(=O)E or an alkylsulfonyl group; Ｄ is alkoxy, cyano, alkoxycarbonyl or alkoxycarbonyloxy; E is alkyl, alkenyl, cycloalkyl, heterocycloalkyl, haloalkyl, haloalkenyl, dialkylamino, N-alkoxy-N-alkylamino, V Ａ phenyl optionally substituted with V Ａ Pyridyl, cycloalkylalkyl, heterocycloalkylalkyl, alkoxyalkyl, alkylthioalkyl, optionally substituted with V Ａ phenylalkyl optionally substituted with V Ａ phenyloxyalkyl optionally substituted with V Ａ phenylalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, heterocycloalkyloxy, haloalkoxy, alkoxyalkoxy, V Ａ phenyloxy optionally substituted with V Ａ naphthyloxy, cycloalkylalkoxy, heterocycloalkylalkoxy, optionally substituted with V Ｂ phenylalkoxy, alkylthio or 2-imidazolidinone, optionally substituted with V; Ａ is a halogen; V Ｂ is halogen or alkyl), or a salt thereof.

2. Y and R Ａ each represents a halogen, an alkyl, an alkenyl, an alkynyl, a cycloalkyl, a haloalkyl, an alkoxy, a haloalkoxy, an alkylsulfonyl, a cyano, or a -C(=O)R Ｂ 2. The pyridazinone compound or a salt thereof according to claim 1, 3. Y and R Ａ 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 １ -C ４ ) haloalkoxy, (C １ -C ４ ) alkylthio, (C １ -C ４ ) alkylsulfinyl, (C １ -C ４ ) alkylsulfonyl, cyano or -C(=O)R Ｂ Z is (C １ -C ５ ) alkyl, (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 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, cyano, nitro, aldehyde, -CH(=NOR Ｃ ), 1,3-dioxan-2-yl or 1,3-dioxolan-2-yl; R Ｂ is a hydrogen atom or (C １ -C ４ ) alkyl; R Ｃ (C １ -C ４ ) alkyl; G is R Ｄ (C １ -C ４ ) alkyl, -C(=O)E or (C １ -C ４ ) alkylsulfonyl; R Ｄ (C １ -C ４ ) alkoxy, cyano, (C １ -C ４ ) alkoxycarbonyl or (C １ -C ４ E is (C) alkoxycarbonyloxy; １ -C ８ ) alkyl, (C ２ -C ８ ) alkenyl, (C ３ -C ６ ) cycloalkyl, heterocycloalkyl, (C １ -C ８ ) haloalkyl, (C ２ -C ８ ) haloalkenyl, (C １ -C ４ )dialkylamino, N-(C １ -C ４ ) alkoxy-N-(C １ -C ４ ) alkylamino, V Ａ phenyl optionally substituted with V Ａ pyridyl optionally substituted with (C ３ -C ６ ) Cycloalkyl(C １ -C ４ ) alkyl, heterocycloalkyl (C １ -C ４ ) alkyl, (C １ -C ４ ) Alkoxy (C １ -C ３ ) alkyl, (C １ -C ４ ) alkylthio (C １ -C ３ ) Alkyl, V Ａ Phenyl (C １ -C ４ ) Alkyl, V Ａ Phenyloxy (C １ -C ３ ) Alkyl, V Ａ Phenyl (C ２ -C ４ ) alkenyl, (C １ -C ７ ) alkoxy, (C ２ -C ７ ) alkenyloxy, (C ２ -C ７ ) alkynyloxy, (C ３ -C ６ ) cycloalkyloxy, heterocycloalkyloxy, (C １ -C ７ ) haloalkoxy, (C １ -C ４ ) Alkoxy (C １ -C ３ ) Alkoxy, V Ａ phenyloxy optionally substituted with V Ａ naphthyloxy optionally substituted with (C ３ -C ６ ) Cycloalkyl(C １ -C ３ ) alkoxy, heterocycloalkyl (C １ -C ３ ) Alkoxy, V Ｂ Phenyl (C １ -C ３ ) alkoxy, (C １ -C ７ ) alkylthio or 2-imidazolidinone, and the heterocycloalkyl and heterocycloalkyl moieties in E are each 3- to 6-membered groups containing, in addition to carbon atoms, one or more atoms selected from oxygen atoms, nitrogen atoms, and sulfur atoms; V Ｂ is halogen or (C １ -C ４ 2. The pyridazinone compound or a salt thereof according to claim 1, wherein the aryl group is 1 or 2.

4. Y and R Ａ 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 １ -C ４ ) haloalkoxy, (C １ -C ４ ) alkylsulfonyl, cyano or -C(=O)R Ｂ 2. The pyridazinone compound or a salt thereof according to claim 1, 5. 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 ４ ) haloalkyl; R １ , R ２ , R ３ and R ４ are 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, (C １ -C ４ ) alkylsulfonyl, cyano, nitro, aldehyde, -CH(=NOR Ｃ ) or 1,3-dioxolan-2-yl; E is (C １ -C ８ ) alkyl, (C ２ -C ８ ) alkenyl, (C ３ -C ６ ) cycloalkyl, heterocycloalkyl, (C １ -C ８ ) haloalkyl, (C １ -C ４ )dialkylamino, N-(C １ -C ４ ) alkoxy-N-(C １ -C ４ ) alkylamino, V Ａ phenyl optionally substituted with V Ａ pyridyl optionally substituted with (C ３ -C ６ ) Cycloalkyl(C １ -C ４ ) alkyl, heterocycloalkyl (C １ -C ４ ) alkyl, (C １ -C ４ ) Alkoxy (C １ -C ３ ) alkyl, (C １ -C ４ ) alkylthio (C １ -C ３ ) Alkyl, V Ａ Phenyl (C １ -C ４ ) Alkyl, V Ａ Phenyloxy (C １ -C ３ ) Alkyl, V Ａ Phenyl (C ２ -C ４ ) alkenyl, (C １ -C ７ ) alkoxy, (C ２ -C ７ ) alkenyloxy, (C ２ -C ７ ) alkynyloxy, (C ３ -C ６ ) cycloalkyloxy, (C １ -C ７ ) haloalkoxy, (C １ -C ４ ) Alkoxy (C １ -C ３ ) Alkoxy, V Ａ phenyloxy optionally substituted with V Ａ naphthyloxy optionally substituted with V Ｂ Phenyl (C １ -C ３ ) alkoxy, (C １ -C ７ 4. The pyridazinone compound or salt thereof according to claim 3, wherein E is alkylthio or 2-imidazolidinone, and the heterocycloalkyl and heterocycloalkyl moieties in E are each a 3- to 6-membered group containing, in addition to carbon atoms, one or more atoms of one or more kinds selected from oxygen atoms, nitrogen atoms and sulfur atoms.

6. Q is Q １ Or Q ３ 2. The pyridazinone compound or a salt thereof according to claim 1, 7. X is CH or C(R Ａ 2. The pyridazinone compound or a salt thereof according to claim 1, wherein 8. The pyridazinone compound or its salt according to claim 1, wherein X is N.

9. When X is CH, n is an integer from 1 to 3, and X is C(R Ａ 2. The pyridazinone compound or a salt thereof according to claim 1, wherein n is 1 or 2 when N is 1 or 2.

10. The pyridazinone compound or its salt according to claim 1, wherein a, b, c and d are each 1 or 2.

11. A pest control agent comprising the compound or salt thereof according to any one of claims 1 to 10 as an active ingredient.

12. An agricultural and horticultural insecticide, acaricide, nematicide or soil pesticide comprising the compound or salt thereof according to any one of claims 1 to 10 as an active ingredient.

13. A method for controlling pests which comprises applying an effective amount of a compound or a salt thereof according to any one of claims 1 to 10.

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