Nematode composition

Abstract

A nematocidal composition is provided that exhibits excellent nematocidal properties.　This invention relates to a nematocidal composition that contains, as an effective component, a compound represented in formula (I) or a salt thereof (the symbols in the formula are as described in the detailed description).

Description

[Technical Field]

[0001] The present invention relates to a nematicidal composition containing, as an active ingredient, a novel formhydrazone compound or a salt thereof that is bonded to a quaternary carbon. [Background technology]

[0002] It is known that compounds having a specific hydrazone structure are useful for controlling various pests. Patent Document 1 describes hydrazone derivatives having a chemical structure such as -CH(Me)- or -CH(i-Pr)-, which are composed of a tertiary carbon, and which are useful as agricultural and horticultural insecticides or nematicides, and methods for using the same. However, this document does not describe specific examples of compounds of the following formula (I), i.e., hydrazone derivatives having a chemical structure characterized by a quaternary carbon, nematicidal compositions containing the same as an active ingredient, or methods for using the same. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2020 / 179910 Summary of the Invention [Problem to be solved by the invention]

[0004] There are various types of nematodes that cause damage to crop production in agriculture and horticulture, and the development of agricultural and horticultural nematicides for the purpose of controlling them is underway. However, continued use of the same agricultural and horticultural pesticide over a long period of time may promote the target nematodes to acquire drug resistance. Therefore, there is a strong demand for the development of new agricultural and horticultural nematicides that have high nematode control effects regardless of the application situation.

[0005] Therefore, an object of the present invention is to provide a nematicidal composition containing, as an active ingredient, a compound represented by the formula (I) below or a salt thereof, which exhibits excellent nematicidal activity. [Means for solving the problem]

[0006] As a result of intensive research to solve the above problems, the present inventors have found that a composition containing a compound represented by formula (I) described below or a salt thereof as an active ingredient exhibits excellent control effects against nematodes.

[0007] That is, the present invention is as follows. [1] Formula (I):

[0008] [ka]

[0009] wherein X is N, CH or CR 4 and A is unsubstituted phenyl or 1 to 5 R 1 is a phenyl substituted with R 1 is halogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or haloalkoxy; R 1 If there are two R 1 together, one or two Z 1 may form a ring which may be substituted with Z 1 is halogen or alkyl, R 2 and R 3 are each alkyl, or R 2 and R 3 together form a (C3-C6)-carbocyclic ring, R 4 is halogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro or cyano; R 5 is CHO, R 6 is H, -SO2CF3, -C(=O)OZ 3, alkyl, alkenyl, alkynyl or alkoxyalkyl, or Z 2 is an aralkyl optionally substituted with Z 2 is an alkoxy; Z 3 is Z 2 aralkyl or alkyl optionally substituted with m is an integer from 0 to 2.] or a salt thereof (hereinafter also referred to as compound (I)) as an active ingredient (hereinafter also referred to as the present composition). [2] Formula (I):

[0010] [ka]

[0011] wherein X is N, CH or CR 4 and A is unsubstituted phenyl or 1 to 5 R 1 is a phenyl substituted with R 1 is halogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or haloalkoxy; R 1 If there are two R 1 together, one or two Z 1 may form a ring which may be substituted with Z 1 is halogen or alkyl, R 2 and R 3 are each alkyl, or R 2 and R 3 together form a (C3-C6) carbocyclic ring, R 4 is halogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro or cyano; R 5 is CHO, R 6 is H, -SO2CF3, -C(=O)OZ 3 , alkyl, alkenyl, alkynyl or alkoxyalkyl, or Z 2 is an aralkyl optionally substituted with Z 2 is an alkoxy; Z 3 is Z 2 aralkyl or alkyl optionally substituted with m is an integer between 0 and 2. A method for controlling nematodes, which comprises applying a nematicidal composition containing an effective amount of a compound represented by the formula (I) or a salt thereof to soil, nematodes or plants. [3] In the compound represented by formula (I) or a salt thereof, A is 1 to 5 R 1 is phenyl substituted with R 1 is halogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or haloalkoxy; R 1 If there are two R 1 together, one or two Z 1 The nematicidal composition according to the above item [1], which is a compound or a salt thereof which may form a ring optionally substituted with: [4] In the compound represented by formula (I) or a salt thereof, A is 1 to 5 R 1 is phenyl substituted with R 1 is halogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or haloalkoxy; R 1 If there are two R 1 together, one or two Z 1 The method for controlling nematodes according to the above item [2], wherein the compound is a compound which may form a ring optionally substituted by the following formula (I) or a salt thereof. [5] Formula (IA):

[0012] [ka] wherein X is N, CH or CR 4A and R 1A is halogen, (C-C)-alkyl, (C-C)-haloalkyl, (C-C)-alkenyl, (C-C)-alkynyl, (C-C)-cycloalkyl, (C-C)-alkoxy, or (C-C)-haloalkoxy, and R 1A If there are two R 1A together, one or two Z 1A may form a ring which may be substituted with Z 1A is halogen or (C1-C6)-alkyl, R 2A and R 3A are each (C1-C6)-alkyl, or R 2A and R 3A together form a (C3-C6)-carbocyclic ring, R 4A is halogen, (C-C)-alkyl, (C-C)-haloalkyl, (C-C)-alkenyl, (C-C)-alkynyl, (C-C)-cycloalkyl, (C-C)-alkoxy, (C-C)-haloalkoxy, (C-C)-alkylthio, (C-C)-alkylsulfinyl, (C-C)-alkylsulfonyl, nitro or cyano, R 6A is H, -SO2CF3, -C(=O)OZ 3A , (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl or (C1-C6)-alkoxy-(C1-C6)-alkyl, or Z 2A may be substituted with (C7-C 12 )-aralkyl, Z 2A is (C1-C6)-alkoxy, Z 3A is Z 2A may be substituted with (C7-C 12 )-aralkyl, or (C1-C6)-alkyl, n is an integer from 1 to 5, and m is an integer of 0 to 2] or a salt thereof. [6] Formula (IB):

[0013] [ka] wherein X is N, CH or CR 4A and R 2A and R 3A are each (C1-C6)-alkyl, or R 2A and R 3A together form a (C3-C6)-carbocyclic ring, R 4A is halogen, (C-C)-alkyl, (C-C)-haloalkyl, (C-C)-alkenyl, (C-C)-alkynyl, (C-C)-cycloalkyl, (C-C)-alkoxy, (C-C)-haloalkoxy, (C-C)-alkylthio, (C-C)-alkylsulfinyl, (C-C)-alkylsulfonyl, nitro or cyano, R 6A is H, -SO2CF3, -C(=O)OZ 3A , (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl or (C1-C6)-alkoxy-(C1-C6)-alkyl, or Z 2A may be substituted with (C7-C 12 )-aralkyl, Z 2A is (C1-C6)-alkoxy, Z 3A is Z 2A may be substituted with (C7-C 12 )-aralkyl, or (C1-C6)-alkyl, and m is an integer of 0 to 2] or a salt thereof. [7] A method for controlling nematodes, which comprises applying a nematicidal composition containing an effective amount of the compound or salt thereof according to [5] or [6] above to soil, nematodes, or plants. [8] An agricultural and horticultural nematicide containing the compound or salt thereof according to [5] or [6] above as an active ingredient. Hereinafter, a compound represented by formula (I) or a salt thereof may be referred to as "compound (I)", a compound represented by formula (IA) or a salt thereof may be referred to as "compound (IA)", and a compound represented by formula (IB) or a salt thereof may be referred to as "compound (IB)". [Effects of the Invention]

[0014] The composition of the present invention is useful as an agricultural and horticultural nematode control agent since it can exert an excellent control effect against nematodes. DETAILED DESCRIPTION OF THE INVENTION

[0015] The substituents and chemical structures of Compound (I), Compound (IA) and Compound (IB) will be explained below.

[0016] R, a substituent on the phenyl of compound (I), 1 The number of substitutions may be one or two or more. When the number of substitutions is two or more, R 1 may be the same or different. R, a substituent on the phenyl of compound (IA), 1A The number of substitutions may be one or two or more. When the number of substitutions is two or more, R 1A may be the same or different.

[0017] In compound (I), pyrazole (X is CR 4 R is a substituent of 4 If the number of substitutions in is 2 or 3, R 4 In compound (I), R, which is a substituent of 1,2,4-triazole (X is N), 4 If the number of substitutions is 2, R 4 In the compound (IA) or the compound (IB), the pyrazole (X is CR 4A R is a substituent of 4A If the number of substitutions in is 2 or 3, R 4A R, which is a substituent of 1,2,4-triazole in compound (IA) or compound (IB), may be the same or different. 4A If the number of substitutions is 2, R4A may be the same or different.

[0018] As used herein, "n-" means "normal," "s-" means "secondary," and "tert-" means "tertiary."

[0019] The halogen or halogen as a substituent includes fluorine, chlorine, bromine, or iodine atoms. The number of halogen as a substituent may be 1 or 2 or more, and when there are 2 or more, the halogen atoms may be the same or different. The halogen substituent may be at any position.

[0020] In the compound (I), the compound (IA) and the compound (IB), "C P -C T " means that the number of carbon atoms is P to T. For example, "C1-C3" means that the number of carbon atoms is 1 to 3. Furthermore, the expression "may be substituted" means that the group is substituted or unsubstituted.

[0021] Alkyl, alkyl moiety, or (C1-C6)-alkyl includes, for example, straight-chain or branched groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, or n-hexyl.

[0022] Examples of alkenyl or (C2-C6)-alkenyl include straight-chain or branched-chain groups 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, and 2,3-dimethyl-2-butenyl. Furthermore, when geometric isomers exist, they may be either the E- or Z-isomer alone, or a mixture of the E- and Z-isomers in any proportion, and are not particularly limited as long as the number of carbon atoms is within the specified range.

[0023] Alkynyl or (C2-C6)-alkynyl includes, for example, straight-chain or branched groups 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, or 5-hexynyl.

[0024] Cycloalkyl, or (C3-C6)-cycloalkyl, includes, for example, groups such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.

[0025] Haloalkyl or (C1-C6)-haloalkyl includes, for example, straight-chain or branched alkyl groups partially or fully substituted by 1 to 7 identical or different halogen atoms, such as chloromethyldifluoromethyl, trifluoromethyl, trichloromethyl, 1,1-dichloro-1-fluoromethyl, 1-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrafluoroethyl, 1,1,2,2-tetrachloroethyl, 1,1,2,2,2-pentafluoroethyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, or 1,1,1,2,3,3,3-heptafluoropropan-2-yl.

[0026] Alkoxy, or (C1-C6)-alkoxy, includes linear or branched groups such as, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, tert-butoxy, n-pentyloxy, neopentyloxy, or n-hexyloxy.

[0027] Haloalkoxy or (C1-C6)-haloalkoxy includes, for example, straight-chain or branched groups partially or fully substituted by 1 to 6 identical or different halogen atoms, such as difluoromethoxy, trifluoromethoxy, 2-chloroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 1,1,2,2,2-pentafluoroethoxy, 2,2,3,3,3-pentafluoropropoxy, or (1,1,1,3,3,3-hexafluoropropan-2-yl)oxy.

[0028] Carbocycles, or (C3-C6)-carbocycles, include saturated rings such as, for example, cyclopropane, cyclobutane, cyclopentane, or cyclohexane.

[0029] Alkylthio or (C1-C6)-alkylthio includes linear or branched groups such as, for example, methylthio, ethylthio, isopropylthio, n-butylthio, isobutylthio, s-butylthio, tert-butylthio, n-pentylthio, neopentylthio, or n-hexylthio.

[0030] Alkylsulfinyl or (C1-C6)-alkylsulfinyl includes linear or branched groups such as, for example, methylsulfinyl, ethylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, s-butylsulfinyl, tert-butylsulfinyl, n-pentylsulfinyl, neopentylsulfinyl, or n-hexylsulfinyl.

[0031] Alkylsulfonyl or (C1-C6)-alkylsulfonyl includes linear or branched groups such as, for example, methylsulfonyl, ethylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, s-butylsulfonyl, tert-butylsulfonyl, n-pentylsulfonyl, neopentylsulfonyl, or n-hexylsulfonyl.

[0032] In compound (I), two R 1 In the embodiment where A is taken together with Z to form a ring, A is one or two Z 1 In addition, in the compound of formula (IA), two R 1A In the embodiment where the phenyl groups are taken together to form a ring, one or two Z 1A Examples include benzodioxolanyl or benzodioxanyl, which may be substituted with Z. 1 or Z 1A If there are two, Z 1 or Z 1A may be the same or different.

[0033] Aralkyl, or (C7-C 12 Z)-aralkyl includes, for example, benzyl, 1-phenylethyl, naphthylmethyl, etc. 2 aralkyl optionally substituted with Z 2 may be substituted with (C7-C 12 )-aralkyl includes p-methoxybenzyl, 2,3-dimethoxybenzyl, and 2,4-dimethoxybenzyl. Z 2 , or Z 2A The number of substitutions may be two or more, and when two or more, they may be the same or different. 2 or Z 2A The substituent position of may be any position.

[0034] In compound (I), "1 to 5 R1 "Phenyl substituted with" refers to 1, 2, 3, 4 or 5 R 1 "Unsubstituted phenyl" means a phenyl substituted with the substituent R 1 In a specific embodiment of compound (I), R 1 The number of substitutions may be an integer from 1 to 2, 1 to 3, 1 to 4, 2 to 3, 2 to 4, 2 to 5, 3 to 4, 3 to 5, or 4 to 5.

[0035] In compound (IA), "n is an integer of 1 to 5" means that n is an integer of 1, 2, 3, 4, or 5. In certain embodiments of compound (IA), n may also be an integer of 1 to 2, 1 to 3, 1 to 4, 2 to 3, 2 to 4, 2 to 5, 3 to 4, 3 to 5, or 4 to 5.

[0036] In compound (IA), R 1A The substituent position of the group may be any position on the phenyl ring. When m is 1 or more, the substituent position of R 4A The substituent position of the group may be either or both of the 3-position and the 5-position of the hetero five-membered ring.

[0037] [ka]

[0038] For example, in compound (IA), when n is 1, R 1 The substituent positions are the same as those of the compounds represented by the following formulae (IAa) to (IAc). Formula (IAa); [ka]

[0039] Formula (IAb); [ka]

[0040] formula(IAc); [ka]

[0041] In compound (IB), when m is 1 or more, R 4A The substituent position of the group may be either or both of the 3-position and the 5-position of the hetero five-membered ring.

[0042] [ka]

[0043] In Compound (I), Compound (IA), and Compound (IB), the expression "m is an integer of 0 to 2" means that m is an integer of 0, 1, or 2. In addition, in certain embodiments of Compound (I), Compound (IA), and Compound (IB), m may be an integer of 0 to 1, or an integer of 1 to 2. In the compounds (I), (IA) and (IB), when m is 0, (R 4 ) m and (R 4A ) m is H, which means that both the 3-position and the 5-position of the heterocyclic five-membered ring are unsubstituted.

[0044] Hereinafter, in the description of compound (I), since compound (I) includes compound (IA) and compound (IB), the description of compound (IA) and compound (IB) is also included. The salt of the compound represented by formula (I) includes any salt that is agriculturally acceptable, and examples thereof include alkali metal salts (e.g., sodium salt, potassium salt, etc.), alkaline earth metal salts (e.g., magnesium salt, calcium salt, etc.), inorganic acid salts (e.g., hydrochloride, perchlorate, sulfate, nitrate, etc.), and organic acid salts (e.g., acetate, methanesulfonate, etc.).

[0045] The compound (I) of the present invention may exist in various isomers, such as optical isomers and geometric isomers, and the present invention includes both each isomer and a mixture of isomers. More specifically, Compound (I) of the present invention has two or more geometric isomers depending on the number of double bonds (carbon-carbon or carbon-nitrogen) in the structural formula. Therefore, the present invention includes all possible geometric isomers and mixtures thereof in any ratio. For example, in the compounds described herein, a bond shown by a wavy line in a structural formula means that any of two or more geometric isomers derived from a double bond (carbon-carbon or carbon-nitrogen) is included. The compound (I) of the present invention also includes various isomers other than those described above within the scope of common general knowledge in the art. Furthermore, various isomers can be prepared using common general knowledge in the art and general experimental techniques.

[0046] Furthermore, depending on the type of isomer, the chemical structure may differ from the structural formula shown, but a person skilled in the art would be able to fully recognize that they are isomers, and therefore it is clear that they are within the scope of the present invention.

[0047] Next, a method for producing compound (I) contained in the present composition will be described. Compound (I) can be produced according to the following Reactions A to O and conventional methods for producing salts, but the method for obtaining Compound (I) is not limited to these methods. For example, Compound (I) can also be produced by applying various substituent conversion reactions well known in the art (e.g., hydrolysis, oxidation, reduction, esterification, amidation, alkylation, halogenation, etc.) to the substituents on phenyl and / or pyrazole or 1,2,4-triazole. In addition, in the production of Compound (I), protection and deprotection reactions commonly used in the art may be applied as necessary.

[0048] Scheme1 Scheme 1 is a method for obtaining a compound of formula (I-2) or formula (2) from a compound of formula (4) by reaction A or reaction B, and a method for obtaining a compound (I-1) from a compound of formula (I-2) or formula (2) by reaction A or reaction B.

[0049] [ka]

[0050] In the formula, A, X, m, R 2 , R 3 , R 4 , and R 5 is as mentioned above. R 6A is -SO2CF3, -C(=O)OZ 3 , alkyl, alkenyl, alkynyl or alkoxyalkyl, or Z 2 and Z is an aralkyl optionally substituted with 2 and Z 3 is as described above. L is a leaving group, more specifically, a chlorine atom, a bromine atom, an iodine atom, or a trifluoromethanesulfonyl group.

[0051] Reaction A Reaction A is a method of reacting a compound of formula (2) with a formylating reagent to obtain a compound (I-1), or a method of reacting a compound of formula (4) with a formylating reagent to obtain a compound of formula (I-2).

[0052] Reaction A can usually be carried out in the presence of a formylating reagent and a solvent. The formylating reagent is not particularly limited as long as the reaction proceeds, and examples thereof include formic acid, N-formylsaccharin, etc. The formylating reagent can be used in an amount of 1 to 10 equivalents, preferably 1 to 2 equivalents, relative to the compound of formula (2) or formula (4). Here, "equivalent" means molar equivalent, and the same applies hereinafter.

[0053] The solvent is not particularly limited as long as it allows the reaction to proceed, and one or more solvents can be appropriately selected from, for example, aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin, and cyclohexane; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane; esters such as methyl formate, ethyl formate, methyl acetate, and ethyl acetate; alcohols such as methanol, ethanol, propanol, and tert-butanol; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, N,N-dimethylformamide (hereinafter also referred to as DMF), N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; and acetic acid. Reaction A can be carried out in the presence of a formate such as methyl formate or ethyl formate, if necessary. The formic acid ester can be used in an amount of 1 to 50 equivalents, preferably 1 to 30 equivalents, relative to the compound of formula (2) or formula (4).

[0054] Reaction A can be carried out in the presence of a dehydrating condensing agent and a base, if necessary. Examples of the dehydration condensation agent include N,N'-dicyclohexylcarbodiimide, chlorosulfonyl isocyanate, N,N'-carbonyldiimidazole, trifluoroacetic anhydride, etc. The dehydration condensation agent can be used in an amount of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to the compound of formula (2) or formula (4). The base can be selected from one or more of alkali metals such as sodium and potassium; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as monomethylamine, dimethylamine, and triethylamine; pyridines such as pyridine and 4-dimethylaminopyridine; and organolithium compounds such as methyllithium, n-butyllithium, and lithium diisopropylamide. The base can be used in an amount of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to the compound of formula (2) or formula (4).

[0055] The reaction temperature is usually about 0° C. to 200° C., preferably about 0° C. to 100° C. The reaction time is usually about 1 hour to 24 hours.

[0056] The compound of formula (2) used in reaction A can be prepared according to reaction B below.

[0057] Reaction B Reaction B is a method of reacting a compound of formula (I-2) with a compound of formula (3) or a protecting reagent to obtain compound (I-1), or a method of reacting a compound of formula (4) with a compound of formula (3) or a protecting reagent to obtain compound of formula (2).

[0058] Reaction B can usually be carried out in the presence of a base and a solvent. The compound of formula (3) or the protecting reagent can be used in an amount of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to the compound of formula (I-2) or the compound of formula (4).

[0059] The base that can be used is the same as that exemplified in the above reaction A. The base can be used in an amount of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to the compound of formula (I-2) or the compound of formula (4).

[0060] The protecting reagent can be appropriately selected from methoxymethyl chloride, benzyl bromide, p-methoxybenzyl chloride, di-tert-butyl dicarbonate, benzyl chloroformate, and the like.

[0061] The solvent is not particularly limited as long as it allows the reaction to proceed, and one or more solvents can be appropriately selected from, for example, aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin, and cyclohexane; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; alcohols such as methanol, ethanol, propanol, and tert-butanol; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; and water.

[0062] The reaction temperature is usually about −78° C. to 200° C., preferably about 0° C. to 100° C. The reaction time is usually about 1 hour to 48 hours.

[0063] The compound of formula (3) can be produced according to known methods, or a commercially available product may be used. The compound of formula (4) can be prepared according to the following reaction H.

[0064] Reaction C Reaction C is a method of converting a compound of formula (I-3) into a compound of formula (I-4) using a compound of formula (b-1).

[0065] [ka]

[0066] In the formula, X, m, R 2 , R3 , R 4 , and R 5 is as mentioned above. A 1 is a fluorine-substituted phenyl, and A 2 is phenyl substituted with hydroxy. 6a is methoxymethyl, benzyl, p-methoxybenzyl, tert-butoxycarbonyl, or benzyloxycarbonyl. Me in formula (b-1) is a methyl group.

[0067] Reaction C can usually be carried out in the presence of a base and a solvent. The compound of formula (b-1) can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to the compound of formula (I-3).

[0068] The base that can be used is the same as that exemplified in the above reaction A. The base can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to the compound of formula (I-3). The solvent is not particularly limited as long as it allows the reaction to proceed, and one or more solvents can be appropriately selected from, for example, aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; and ketones such as acetone and methyl ethyl ketone.

[0069] The reaction temperature is usually about 0 to 150°C, preferably about 50 to 100°C, and the reaction time is usually about 1 to 24 hours, preferably about 1 to 12 hours.

[0070] Reaction D Reaction D is a method for converting a compound of formula (I-4) to a compound of formula (I-5) using a compound of formula (b-2), a compound of formula (b-3), or a haloalkylating agent.

[0071] [ka]

[0072] In the formula, X, m, R 2 , R 3 , R 4 , R 5 , R 6a , L and A 2 is as mentioned above, and A 3 HA-OR A-1 is phenyl substituted with R A-1 is alkyl or haloalkyl.

[0073] Reaction D can usually be carried out in the presence of a base and a solvent. Alternatively, it can be carried out in the presence of triphenylphosphine, diethyl azodicarboxylate, and a solvent, similar to a general Mitsunobu reaction. Examples of haloalkylating agents include bromodifluoromethyltrimethylsilane and Togni reagent. The compound of formula (b-2), the compound of formula (b-3), or the haloalkylating agent can be used in an amount of 1 to 3 equivalents, preferably 1 to 2 equivalents, relative to the compound of formula (I-4). Triphenylphosphine can be used in an amount of 1 to 3 equivalents, preferably 1 to 1.5 equivalents, relative to the compound of formula (I-4). Diethyl azodicarboxylate can be used in an amount of 1 to 3 equivalents, preferably 1 to 1.5 equivalents, relative to the compound of formula (I-4).

[0074] The base that can be used is the same as that exemplified in the above reaction A. The base can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to the compound of formula (I-4). As the solvent, those exemplified in the above reaction B can be used.

[0075] The reaction temperature is usually about −78 to 100° C., preferably about 0 to 50° C., and the reaction time is usually about 0.1 to 24 hours, preferably about 0.1 to 12 hours.

[0076] Reaction E Reaction E is a method of deprotecting a compound of formula (I-5) to convert it into a compound of formula (I-6).

[0077] [ka]

[0078] The symbols in the formula are as defined above.

[0079] Reaction E can be carried out under general deprotection reaction conditions, such as acidic conditions, oxidation conditions, or catalytic reduction conditions. Acidic conditions are typically carried out in the presence of an acid and a solvent, with examples of acids such as hydrochloric acid and trifluoroacetic acid. The acid can be used in an amount of 1 to 10 equivalents, preferably 1 to 3 equivalents, relative to the compound of formula (I-5). Oxidation conditions are typically carried out in the presence of an oxidizing agent and a solvent, with examples of oxidizing agents such as 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The oxidizing agent can be used in an amount of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to the compound of formula (I-5). Catalytic reduction conditions are typically carried out under a hydrogen atmosphere in the presence of a catalyst and a solvent, with examples of catalysts such as platinum, platinum oxide, platinum black, Raney nickel, palladium, palladium-carbon, rhodium, and rhodium-alumina. The catalyst can be used in an amount of 0.01 to 1 equivalent, preferably 0.1 to 1 equivalent, relative to the compound of formula (I-5).

[0080] As the solvent, those exemplified in the above reaction B can be used.

[0081] The reaction temperature is usually about −30 to 100° C., preferably about 0 to 50° C., and the reaction time is usually about 0.1 to 48 hours, preferably about 1 to 24 hours.

[0082] Reaction F Reaction F is a method for converting a compound of formula (I-8) into a compound of formula (I-7).

[0083] [ka]

[0084] In the formula, X, m, R 2 , R 3 , R 4 , R 5 and R 6a is as mentioned above. A 4 is phenyl substituted with Y, and A 5 is R A-2 Y is a halogen atom, more specifically a chlorine atom, a bromine atom, or an iodine atom, and R A-2 is alkyl, alkenyl, alkynyl or cycloalkyl.

[0085] Reaction F can usually be carried out by reacting a compound of formula (I-8) with an organometallic reagent in the presence of a transition metal catalyst, a solvent and an inert gas, optionally with the addition of a base.

[0086] The organometallic reagent is not particularly limited as long as the reaction proceeds, and examples thereof include Grignard reagents, organozinc reagents, and organoboron compounds. These organometallic reagents can be prepared according to known methods, or commercially available products may be used. The organometallic reagent can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to the compound of formula (I-8).

[0087] Examples of transition metal catalysts include catalysts containing transition metals such as palladium, rhodium, ruthenium, nickel, cobalt, and molybdenum. Transition metal catalysts with various known structures used in cross-coupling reactions of organic halides can be used, and transition metal catalysts containing palladium are particularly useful for this reaction. Examples include palladium-carbon, palladium chloride, palladium acetate, dichlorobis(acetonitrile)palladium, bis(dibenzylideneacetone)palladium, dichlorobis(triphenylphosphine)palladium, tetrakis(triphenylphosphine)palladium, and dichlorobis(1,4-bis(diphenylphosphino)butane)palladium. Furthermore, tertiary phosphines and tertiary phosphites can be used as ligands, if necessary. Tertiary phosphines and tertiary phosphites include triphenylphosphine, phenyldimethylphosphine, tri-o-tolylphosphine, tri-p-tolylphosphine, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,1'-bis(diphenylphosphino)ferrocene, and triphenylphosphite. The transition metal catalyst can be used in an amount of 0.001 to 0.5 equivalents, preferably 0.05 to 0.2 equivalents, relative to the compound of formula (I-8). The ligand can be used in an amount of typically 1 to 50 equivalents, preferably 1 to 10 equivalents, relative to 1 equivalent of the transition metal catalyst. However, depending on the reaction conditions, amounts outside this range can also be used.

[0088] Examples of the base include alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; alkali metal bicarbonates such as sodium bicarbonate; alkaline earth metal carbonates such as calcium carbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; and organic amines such as triethylamine, diisopropylethylamine, pyridine, 4-(N,N-dimethylamino)pyridine, and imidazole. The base can be used in an amount of 1 to 20 equivalents, preferably 1 to 10 equivalents, relative to the compound of formula (I-8).

[0089] The solvent is not particularly limited as long as it allows the reaction to proceed, and one or more solvents can be appropriately selected from, for example, aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, and pyridine; nitriles such as acetonitrile, propionitrile, and acrylonitrile; ketones such as acetone and methyl ethyl ketone; alcohols such as methanol, ethanol, propanol, and tert-butanol; and water.

[0090] Examples of the inert gas include nitrogen gas and argon gas.

[0091] The reaction temperature is usually about −100 to 200° C., preferably about −78 to 100° C., and the reaction time is usually about 0.5 to 96 hours, preferably about 1 to 48 hours.

[0092] Reaction G Reaction G is a method for converting a compound of formula (I-10) into a compound of formula (I-9).

[0093] [ka]

[0094] In the formula, A, X, m, R 2 , R 3 , R 5 and R 6a is as mentioned above. R 4-1 is a halogen, more specifically a chlorine atom, a bromine atom, or an iodine atom. 4-2 is alkyl, alkenyl, alkynyl, or cycloalkyl.

[0095] Reaction G can be carried out in accordance with Reaction F.

[0096] Reaction H Reaction H is a method of reacting a compound of formula (5) with a compound of formula (6) or hydrazine to obtain a compound of formula (2) or a compound of formula (4).

[0097] [ka]

[0098] The symbols in the formula are as defined above.

[0099] Reaction H can usually be carried out in the presence of a solvent, or can be carried out in the presence of an acid, if necessary. The compound of formula (6) or hydrazine can be used in an amount of 1 to 10 equivalents, preferably 1 to 3 equivalents, relative to the compound of formula (5).

[0100] The acid is not particularly limited as long as it allows the reaction to proceed, and one or more acids can be appropriately selected from, for example, inorganic acids such as hydrochloric acid and sulfuric acid; organic acids such as acetic acid, propionic acid, methanesulfonic acid, p-toluenesulfonic acid, etc. The acid can be used in an amount of 0.01 to 2 equivalents, preferably 0.01 to 1 equivalent, relative to the compound of formula (5).

[0101] As the solvent, those exemplified in the above reaction B can be used.

[0102] The reaction temperature is usually about 0° C. to 200° C., preferably about 20° C. to 150° C. The reaction time is usually about 1 hour to 72 hours.

[0103] The compound of formula (5) used in reaction H can be produced by the following method of reaction I or reaction J, for example, the method described in U.S. Pat. No. 4,829,075, or a method analogous thereto. The compound of formula (6) can be produced by a known method, or a commercially available product may be used.

[0104] Reaction I Reaction I is a method of reacting a compound of formula (7) with a compound of formula (8) to obtain a compound of formula (5).

[0105] [ka]

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

[0107] Reaction I can usually be carried out in the presence of a base and a solvent. The base and solvent that can be used are those listed in Reaction B above. The compound of formula (8) can be used in an amount of 1 to 2 equivalents, preferably 1 to 1.2 equivalents, relative to the compound of formula (7). The base can be used in an amount of 0.5 to 3 equivalents, preferably 0.5 to 1 equivalent, relative to the compound of formula (7).

[0108] The reaction temperature is usually about 0° C. to 150° C., preferably 0° C. to 100° C. The reaction time is usually about 1 hour to 48 hours.

[0109] The compound of formula (7) used in reaction I can be produced according to the methods described in, for example, JP 2021-035913 A, JP 2021-035914 A, etc., or methods similar thereto, or commercially available products may be used. The compound of formula (8) can be produced according to the methods described in, for example, WO 2010 / 029461, WO 2015 / 095788, WO 2017 / 019804, etc., or methods similar thereto, or commercially available products may be used.

[0110] Reaction J Reaction J is a method of reacting a compound of formula (9) with a compound of formula (10) to obtain a compound of formula (5).

[0111] [ka]

[0112] The symbols in the formula are as defined above.

[0113] Reaction J can be carried out in accordance with Reaction B.

[0114] The reaction temperature is usually about -78°C to 100°C, preferably about -78°C to 80°C, and the reaction time is usually about 1 hour to 48 hours, preferably about 1 hour to 24 hours.

[0115] The compound of formula (9) used in reaction J can be produced according to the following reaction K. The compound of formula (10) can be produced according to a known method, or a commercially available product may be used.

[0116] Reaction K Reaction K is a method in which a compound of formula (11) is reacted with a compound of formula (8) to obtain a compound of formula (9).

[0117] [ka] The symbols in the formula are as defined above.

[0118] Reaction K can be carried out in accordance with Reaction I.

[0119] The compound of formula (11) used in reaction K can be produced according to the methods described in, for example, International Publication No. 2010 / 121022, European Journal of Medicinal Chemistry, Vol. 148, pp. 86-94 (2018), or methods similar thereto, or commercially available products may be used.

[0120] Reaction L Reaction L is a method of reacting a compound of formula (12) with a compound of formula (8) to obtain a compound of formula (I-2).

[0121] [ka]

[0122] The symbols in the formula are as defined above.

[0123] Reaction L can usually be carried out in the presence of a base and a solvent. The solvents that can be used are those exemplified in the above reaction B. The compound of formula (8) can be used in an amount of 1 to 2 equivalents, preferably 1 to 1.2 equivalents, relative to the compound of formula (12).

[0124] The base can be selected from one or more of the following: alkali metals such as sodium and potassium; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as monomethylamine, dimethylamine, and triethylamine; pyridines such as pyridine and 4-dimethylaminopyridine; organolithium compounds such as methyllithium, n-butyllithium, and lithium diisopropylamide; and silicon compounds such as lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, and potassium bis(trimethylsilyl)amide. The base can be used in an amount of 0.5 to 5 equivalents, preferably 1 to 2 equivalents, relative to the compound of formula (12).

[0125] The reaction temperature is usually about −20° C. to 100° C., preferably about 0° C. to 50° C. The reaction time is usually about 0.1 to 48 hours, preferably about 0.5 to 24 hours.

[0126] The compound of formula (12) used in reaction L can be prepared according to the method of reaction M below.

[0127] Reaction M Reaction M is a method of reacting a compound of formula (13) with a halogenating agent to obtain a compound of formula (12).

[0128] [ka]

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

[0130] Reaction M can be carried out usually in the presence of a halogenating agent (e.g., a chlorinating agent, a brominating agent, or an iodinating agent) and a solvent, and optionally in the presence of a base. The halogenating agent can be used in an amount of 1 to 2 equivalents, preferably 1 to 1.5 equivalents, relative to the compound of formula (13).

[0131] The chlorinating agent may be one or more appropriately selected from, for example, chlorine, N-chlorosuccinimide, sulfuryl chloride, etc.; the brominating agent may be one or more appropriately selected from, for example, bromine, N-bromosuccinimide, trimethylphenylammonium tribromide, etc.; and the iodinating agent may be one or more appropriately selected from, for example, iodine, N-iodosuccinimide, etc.

[0132] The solvent is not particularly limited as long as it allows the reaction to proceed, and one or more solvents can be appropriately selected from, for example, aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin, and cyclohexane; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane; esters such as methyl formate, ethyl formate, methyl acetate, and ethyl acetate; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, and pyridine; organic acids such as acetic acid and propionic acid; and water.

[0133] The base may be, for example, lithium diisopropylamide, etc. The base can be used in an amount of 1 to 2 equivalents, preferably 1 to 1.2 equivalents, relative to the compound of formula (13). When the reaction is carried out in the presence of a base, the solvent can usually be one or more appropriately selected from ethers such as tetrahydrofuran and diethyl ether.

[0134] In reaction M, an organic acid such as acetic acid or propionic acid or a Lewis acid such as aluminum chloride can be used as a catalyst, if necessary. In addition, an excess of the organic acid can be used as a solvent, which also serves as a catalyst.

[0135] The reaction temperature is usually about -100°C to 150°C, preferably about -78°C to 100°C. The reaction time is usually about 0.1 to 48 hours, preferably about 0.5 to 24 hours. When carried out in the presence of a base, the reaction temperature is usually about -100°C to 50°C, preferably about -78°C to 20°C, and the reaction time is usually about 0.1 to 12 hours, preferably about 0.5 to 6 hours. When carried out in the presence of an acid, the reaction temperature is usually about 0°C to 150°C, preferably about 20°C to 120°C, and the reaction time is usually about 0.1 to 48 hours, preferably about 1 to 24 hours.

[0136] The compound of formula (13) used in reaction M can be prepared according to the method of reaction N or reaction O below.

[0137] Reaction N Reaction N is a method in which a compound of formula (14) is reacted with a formylating agent to obtain a compound of formula (13).

[0138] [ka]

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

[0140] Reaction N can be carried out in accordance with Reaction A. Examples of the formylation reagent used in Reaction N include the compounds exemplified in Reaction A.

[0141] The compound of formula (14) used in reaction N can be prepared according to the method of reaction O below.

[0142] Reaction O Reaction O is a method of reacting a compound of formula (15) with a compound of formula (16) or hydrazine to obtain a compound of formula (13) or a compound of formula (14).

[0143] [ka]

[0144] The symbols in the formula are as defined above.

[0145] Reaction O can be carried out in accordance with reaction H.

[0146] The compound of formula (15) used in reaction O can be produced according to the methods described in, for example, JP 2021-035913 A, JP 2021-035914 A, WO 2006 / 016708 A, or methods similar thereto, or a commercially available product may be used. The compound of formula (16) can be produced according to known methods, or a commercially available product may be used.

[0147] The application scene, application form, treatment method, etc. of the present composition will be explained below. Nematodes can be controlled by applying an effective amount of the composition directly to the nematodes and / or to the soil or plant tissue where the nematodes live. The habitat includes not only the location where the nematodes live but also the location where they are expected to live. The plant tissue refers to the above-ground parts (e.g., stems, leaves, trunks), underground parts (e.g., roots), or seeds of the plant to which the composition 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).

[0148] The present composition can be used to treat, for example, nematodes of the genus Meloidogyne, nematodes of the genus Pratylenchus, nematodes of the genus Ditylenchus, nematodes of the genus Heterodera, nematodes of the genus Globodera, nematodes of the genus Aphelenchoides, nematodes of the genus Aphelenchus, nematodes of the genus Radopholus, nematodes of the genus Tylenchulus, nematodes of the genus Rotylenchulus, nematodes of the genus Rotylenchus, nematodes of the genus Anguina, nematodes of the genus Belonolaimus, nematodes of the genus Bursaphelenchus, nematodes of the genus Criconema, nematodes of the genus Criconemoides, nematodes of the genus Mesocriconema, It can control nematodes belonging to the genus Dolichodorus, Helicotylenchus, Hirschmanniella, Hoplolaimus, Nacobbus, Longidorus, Scutellonema, Trichodorus, Paratrichodorus, Tylenchorhynchus, and Xiphinema, and is particularly effective in controlling nematodes belonging to the genus Meloidogyne, Pratylenchus, Heterodera, and Globodera.

[0149] Specific examples of the nematode include the following: Nematodes of the genus Meloidogyne, such as the sweet potato root-knot nematode (Meloidogyne incognita), the northern root-knot nematode (Meloidogyne hapla), the arenaria root-knot nematode (Meloidogyne arenaria), and the Java root-knot nematode (Meloidogyne javanica); nematodes of the genus Pratylenchus, such as the northern root-leach nematode (Pratylenchus penetrans), the southern root-leach nematode (Pratylenchus coffeae), the channel root-leach nematode (Pratylenchus loosi), and the walnut root-leach nematode (Pratylenchus vulnus); nematodes of the genus Ditylenchus, such as the potato root-leach nematode (Ditylenchus destructor) and the soybean cyst nematode (Ditylenchus dipsaci); Nematodes of the genus Heterodera, such as the sugar beet cyst nematode (Heterodera schachtii), clover cyst nematode (Heterodera trifolii), etc.; nematodes of the genus Globodera, such as the potato cyst nematode (Globodera rostochiensis), potato white cyst nematode (Globodera pallida), etc.; nematodes of the genus Aphelenchoides, such as the rice root nematode (Aphelenchoides besseyi), strawberry nematode (Aphelenchoides fragariae), peel nematode (Aphelenchoides ritzemabosi), etc.; nematodes of the genus Aphelenchus, such as the false root nematode (Aphelenchus avenae), etc.; nematodes of the genus Radopholus, such as the banana root nematode (Radopholus similis), etc.; nematodes of the genus Tylenchulus Tylenchulus nematodes such as Rotylenchulus reniformis, RotylenchulusNematodes of the genus Rotylenchus such as Rotylenchus robustus, etc., nematodes of the genus Anguina such as Anguina tritici, etc., nematodes of the genus Belonolaimus such as Belonolaimus longicaudatus, nematodes of the genus Bursaphelenchus such as the pinewood nematode Bursaphelenchus xylophilus and Bursaphelenchus cocophilus, nematodes of the genus Criconema such as Criconema jaejuense and Criconema palliatum, nematodes of the genus Criconemoides such as Criconemoides informis and Criconemoides morgensis, nematodes of the genus Mesocriconema such as Mesocriconema xenoplax and Mesocriconema curvatum, nematodes of the genus Dolichodorus such as Dolichodorus heterocephalus, nematodes of the genus Helicotylenchus pseudorobustus and Helicotylenchus Nematodes of the genus Helicotylenchus such as Hirschmanniella multicinctus, etc.; nematodes of the genus Hirschmanniella such as Hirschmanniella diversa (lotus root nematode) and Hirschmanniella oryzae (rice root nematode), etc.; nematodes of the genus Hoplolaimus such as Hoplolaimus columbus and Hoplolaimus magnistylus, etc.; nematodes of the genus Nacobbus such as Nacobbus aberrans (false root nematode) and Nacobbus dorsalis, etc.; nematodes of the genus Longidorus such as Longidorus martini and Longidorus diadecturus, etc.; nematodes of the genus Scutellonema such as Scutellonema brachyurum and Scutellonema bradys, etc.; nematodes of the genus Trichodorus cedarus), etc., Trichodorus genus nematodes, Paratrichodorusnematodes of the genus Paratrichodorus such as Paratrichodorus minor (Paratrichodorus porosus) and Paratrichodorus minor; nematodes of the genus Tylenchorhynchus such as Tylenchorhynchus claytoni (Tylenchorhynchus claytoni); nematodes of the genus Xiphinema such as Xiphinema americanum (Xiphinema index);

[0150] The plants to which the composition is applied are not particularly limited as long as they are agriculturally and horticulturally useful, and examples thereof include fruit vegetables such as tomatoes, cherry tomatoes, bell peppers, eggplants, cucumbers, zucchinis, watermelons, melons, pumpkins, okra, chili peppers, snow cucumbers, wax gourds, bitter melons, and Japanese melons, lettuce, leaf lettuce, spinach, cabbage, onions, garlic, asparagus, broccoli, cauliflower, Chinese cabbage, morning glory, leeks, Leafy vegetables such as Mizuna, Shiso, Komatsuna, and celery; root vegetables such as potato, sweet potato, radish, carrot, 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, and berries. Fruit trees, fruits and nuts such as dough, strawberries, walnuts, almonds, bananas, figs, pineapples, peaches, nectarines, cherries, apricots, coconuts, avocados, persimmons, plums, pistachios, kiwifruit, and loquats; grasses such as Korean lawn grass and bentgrass; chrysanthemums, lilies, roses, carnations, dahlias, gerberas, saintpaulias, tulips, daffodils, petunias, lily of the valley, peonies, cyclamens, Examples of plants include flowering plants such as balsam and lisianthus, trees and flowering shrubs such as pine, cedar, cypress and azalea, industrial crops such as cotton, rapeseed, beet, tea, tobacco, coffee, olive, sugarcane, hops, sesame, parsley, thyme, rosemary, basil and lavender, ornamental plants such as orchids, cacti and ferns, and pasture grasses such as clover, alfalfa, orchard grass and Johnson grass. 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, the useful plants of the present invention also include transformed plants produced by genetic recombination techniques or gene editing techniques. 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.

[0151] The present composition is usually prepared by mixing Compound (I) with various agricultural and horticultural adjuvants and formulated into various forms such as dusts, granules, water dispersible granules, wettable powders, aqueous suspensions, oily suspensions, water-soluble agents, emulsions, liquids, pastes, aerosols, and micro-sprays, but can be in any formulation form commonly used in the field as long as it is suitable for the purpose of the present invention. Among these, from the viewpoint of the method of application to soil, granules, aqueous suspensions, oily suspensions, emulsions, and liquids are preferred. 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 the like. One or more of these adjuvant components may be used, as appropriate, as long as they do not deviate from the objectives of the present invention. 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 of Compound (I) to various adjuvants (Compound (I):adjuvant) is generally 0.001:99.999 to 95:5, preferably 0.005:99.995 to 90:10, in terms of weight ratio. When actually using these formulations, they can be used as is or diluted to a predetermined concentration with a diluent such as water, and various spreading agents (surfactants, vegetable oil, mineral oil, etc.) can be added as needed.

[0152] The application of the present composition cannot be unambiguously defined due to differences in weather conditions, formulation, target crop, application time, application location, nematode species and occurrence status, etc., but the composition or its diluted form can be applied by commonly used application methods, such as soil treatment, foliage treatment, irrigation treatment, seed treatment, trunk injection treatment, or application to rice seedling boxes. Generally, for soil treatment, foliage treatment, and irrigation treatment, the appropriate application amount is approximately 0.01 g to 50,000 g of the present composition per hectare, preferably approximately 1 g to 30,000 g. For seed treatment, the appropriate application amount is approximately 0.01 g to 200 g, preferably approximately 0.05 g to 100 g per kg of seeds. For rice seedling box application, the appropriate application amount is approximately 0.001 g to 3,000 g, preferably approximately 0.01 g to 1,000 g of the present composition per seedling box. In the case of trunk injection treatment, the appropriate amount of application of the present composition per tree can be about 0.001 g to 5,000 g, preferably about 0.01 g to 3,000 g.

[0153] Examples of soil treatment methods include preparing a liquid formulation (such as a liquid agent, an aqueous suspension, an oily suspension, or an emulsion) or a solid formulation (such as a granule, a dust, a wettable powder, a water-soluble agent, a water-dispersible granule, or a water-soluble granule), and then spraying and mixing the formulation directly or diluted with water over the entire surface of the soil before transplanting or sowing plants; spraying the formulation into a hole (planting hole) made for planting plants; or spraying the formulation into a shallow trench dug to a certain width for sowing or planting plants. Examples of foliar treatment include preparing the composition as a liquid formulation (such as a liquid agent, aqueous suspension, oily suspension, or emulsion) or a solid formulation (such as a wettable powder, water-soluble powder, water-dispersible granules, or water-soluble granules), diluting it with water, and spraying the dilution over the entire plant body. Examples of irrigation treatment include a method in which the composition 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. Seed treatment methods include, for example, preparing the composition 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 it with seeds as is or after diluting it in water to allow it to adhere to the seed surface; mixing it with a coating material and allowing it to adhere to the seed surface; spraying it onto seeds to allow it to adhere; and soaking seeds to allow the agent to penetrate. Application to rice seedling boxes includes, for example, preparing the composition into a solid formulation (granules, dust, etc.) or a liquid formulation (aqueous suspension, oily suspension, liquid, etc.), and spraying it 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 into the paddy field. Further examples include mixing the composition with the growing soil at the time of sowing into the seedling boxes, for example, preparing the composition into a solid formulation (granules, dust, water dispersible granules, etc.) and mixing it with the entire bed soil, covering soil, or growing soil. Examples of trunk injection treatment include a method in which the present composition 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.

[0154] The present composition can be mixed or used in combination with other ingredients selected from other agricultural and horticultural chemicals, fertilizers, phytotoxicity safeners, etc., and in this case, even more excellent effects and activities may be exhibited. The term "mixed or combined use" means that the present composition and other components are used simultaneously, separately or at intervals. Other agricultural and horticultural chemicals include herbicides, insecticides, acaricides, nematicides, soil pesticides, fungicides, antivirals, attractants, antibiotics, plant hormones, and plant growth regulators. In particular, mixed nematicidal compositions prepared by combining or using one or more active ingredient compounds of other insecticides and / or nematicides with the present composition may favorably improve the scope of application, timing of application, and control activity. The present composition and the active ingredient compounds of other insecticides and / or nematicides may be formulated separately and then mixed together for application, or both may be formulated together for application. Such mixed nematicidal compositions are also included in the present invention.

[0155] The mixing ratio of Compound (I) and the active ingredient compounds of other insecticides and / or nematicides (Compound (I):active ingredient compounds) cannot be generally determined due to differences in weather conditions, formulation, target crop, application time, application location, type and occurrence of nematodes, etc., but is generally 1:300 to 300:1, 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 nematodes, or in some cases, a method for controlling nematodes and pest insects, by applying such a mixed nematicidal composition.

[0156] More specific examples of the pests include the following: Aphids such as the green peach aphid and the cotton aphid; Lepidoptera pests such as the diamondback moth, armyworm, common cutworm, codling moth, ballworm, tobacco moth, gypsy moth, rice leafroller, smaller tea tortrix, cutworm moth, turnip moth; Coleoptera pests such as the Colorado potato beetle, cucumber beetle, scarab beetles; Planthoppers such as the brown planthopper and the white-backed planthopper; Leafhoppers; Fungi Examples of pests include caterpillars; stink bugs; whiteflies such as tobacco whitefly; thrips; grasshoppers; flower flies; ants; gastropods such as slugs and snails; plant-parasitic mites such as two-spotted spider mite, false spider mite, Kanzawa spider mite, citrus red mite, apple red mite, tea dust mite, citrus rust mite, bulb mite, and flour mite; isopods such as pill bugs and woodlice; and the like.

[0157] When applying the nematicidal composition containing compound (I), other agricultural and horticultural chemicals such as fungicides, insecticides, acaricides, nematicides, soil pesticides, antiviral agents, attractants, herbicides, plant growth regulators, etc. may also be used in combination.

[0158] Among the above-mentioned other agricultural and horticultural agents, the active ingredient compounds (common names or Japan Plant Protection Association test codes) of the insecticides, nematicides, miticides, or soil pesticides can be appropriately selected, for example, from 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 naturally included. Profenofos, dichlorvos, fenamiphos, fenitrothion, EPN (O-ethyl-O-4-nitrophenyl phenylphosphonothioate, O-ethyl-O-4-nitrophenyl Phenylephosphonothioate, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiofos, fosthiazate, cadusafos, disulfoton, isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate, sulprofos, thiometon, vamidothion, pyraclofos, pyridaphenthion, pirimiphos Pirimiphos-methyl, propaphos, phosalone, formothion, malathion, tetrachlorvinphos, chlorfenvinphos, cyanophos, trichlorfon, methidathion, phenthoate, ESP (oxydeprofos), azinphos-methyl, fenthion, heptenophos, methoxychlor, parathion, phosphocarb, demeton-S-methyl, monocrotophos,Organophosphate compounds such as 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, XMC (3,5-xylyl methylcarbamate), and fenothiocarb; Nereistoxin derivatives such as cartap, thiocyclam, thiocyclam hydrochloride, bensultap, thiosultap, monosultap (also known as thiosultap-monosodium), bisultap (also known as thiosultap-disodium), and polythialan; Organochlorine compounds such as dicofol, tetradifon, endosulfan, dienochlor, and dieldrin; Fenvalerate, permethrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, theta-cypermethrin, beta-cypermethrin, deltamethrin, cyhalothrin, gamma-cyhalothrin (g amma-cyhalothrin, lambda-cyhalothrin, tefluthrin, kappa-tefluthrin, etofenprox, flufenprox, cyfluthrin, beta-cyfluthrin, fenpropathrin, flucythrinate, fluvarine fluvalinate, cycloprothrin, pyrethrins, esfenvalerate, tetramethrin, resmethrin, protrifenbute, bifenthrin, kappa-bifenthrin, acrinathrin, allethrin, tau-fluvalinate pyrethroids such as tau-fluvalinate, tralomethrin, profluthrin, metofluthrin, epsilon-metofluthrin, heptafluthrin, phenothrin, flumethrin, momfluorothrin, and silafluofen; 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, fipronil, ethiprole, acetoprole, pyrafluprole, pyriprole, cyenopyrafen, flufiprole, tebufenpyrad, and tolfenpyrad; Diamide compounds such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole, flubendiamide, tetrachlorantraniliprole, cyhalodiamide, fluchlordiniliprole, and thiolanthraniliprole; 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 and spiropidione; Strobilurin compounds such as fluacrypyrim and pyriminostrobin; Pyrimidinamine compounds such as flufenerim and pyrimidifen; Triazine compounds such as cyromazine; hydrazone compounds such as hydramethylnon; Thiourea compounds such as diafenthiuron and chloromethiuron; Formamidine compounds such as amitraz, chlordimeform, and chloromebuform; Pyridine azomethine compounds such as pymetrozine and pyrifluquinazone; Isoxazoline compounds such as afoxolaner, fluralaner, fluxametamide, and sarolaner; Other compounds include buprofezin, hexythiazox, triazamate, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, 1,3-dichloropropene (1,3-dichloropropene, benclothiaz, bifenazate, propargite, clofentezine, metaflumizone, cyflumetofen, fenazaquin, amidoflumet, sulfluramid, hydramethylnon, metaldehyde, sulfoxaflor, fluensulfone, verbutin, dichloromezotiaz, triflumezopyrim, fluhexafon, tioxazafen, afidopiropen ( Compounds such as afidopyropen, flometoquin, flupyradifurone, fluazaindolizine, acinonapyr, benzpyrimoxan, flupyrimin, oxazosulfyl, tyclopyrazoflor, broflanilide, isocycloseram, dimpropyridaz, flupentiofenox, nicofluprole, cyproflanilide, spidoxamat, cyclobutrifluram, fenmezoditiaz, and trifluenfuronate. The compound of the present invention may be applied in combination 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, Bacillus licheniformis, Bacillus firmus, Pasteuria nishizawae, Myrothecium verrucaria, Burkholderia rinojensis, or Chromobacterium subtsugae, insect pathogenic virus agents, insect pathogenic fungi agents, nematode pathogenic fungi agents, etc.; Antibiotics and semi-synthetic antibiotics such as abamectin, emamectin benzoate, ivermectin, milbemectin, milbemycin oxime, lepimectin, spinosad, spinetoram;

[0159] Among the above-mentioned other agricultural and horticultural agents, the active ingredient compounds of the fungicides (common names or Japan Plant Protection Association test codes) can be appropriately selected, for example, from the following compound group. Even if not specifically stated, when these compounds have various structural isomers such as salts, alkyl esters, and optical isomers, these are of course also included.

[0160] Anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, and cyprodinil; Triazolopyrimidine compounds such as ametoctradin; Pyridinamine compounds such as fluazinam; Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, oxpoconazole fumarate azole compounds such as fumarate, prothioconazole, triadimenol, flutriafol, difenoconazole, fluquinconazole, fenbuconazole, bromuconazole, diniconazole, tricyclazole, simeconazole, pefurazoate, ipconazole, imibenconazole, azaconazole, triticonazole, imazalil, ipfentrifluconazole, and mefentrifluconazole; quinoxaline compounds such as quinomethionate; Dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, and thiram; Organochlorines such as fthalide, chlorothalonil, and quintozene; Imidazole compounds such as benomyl, thiophanate-methyl, carbendazim, thiabendazole, and fuberiazole; cyanoacetamide compounds such as cymoxanil; Acylamino acid compounds such as metalaxyl, metalaxyl-M (also known as mefenoxam), oxadixyl, ofurace, benalaxyl, benalaxyl-M (also known as chiralaxyl, furalaxyl), and valifenalate; Anilides such as cyprofuram, carboxin, oxycarboxin, thifluzamide, boscalid, fenhexamid, isotianil, tiadinil, and pyraziflumid; Sulfamide compounds such as dichlofluanid; Copper compounds such as cupric hydroxide, oxine copper, anhydrous copper sulfate, copper nonylphenolsulfonate, copper 8-hydroxyquinoline, and copper dodecylbenzenesulfonate bisethylenediaminecopper(II) complex (also known as DBEDC); Organophosphates such as fosetyl-Al, tolclofos-methyl, edifenphos, and iprobenfos; Phthalimide compounds such as captan, captafol, and folpet; Dicarboximide compounds such as procymidone, iprodione, and vinclozolin; benzanilide compounds such as flutolanil, mepronil, and benodanil; Amide compounds such as carpropamid, diclocymet, silthiopham, and fenoxanil; pyrazolecarboxamide compounds such as benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, pydiflumetofen, sedaxane, isoflucipram, inpyrfluxam, and pyrapropoyne; benzamide compounds such as fluopicolide, fluopyram, zoxamide, and fluopimomide; Furanilide compounds such as fenfuram; Thiophene amide compounds such as isofetamide; Piperazine compounds such as triforine; Pyridine compounds such as pyrifenox, pyrisoxazole, and aminopyrifen; Pyrimidine compounds such as fenarimol, ferimzone, and nuarimol; Piperidine compounds such as fenpropidin; Morpholine compounds such as fenpropimorph and tridemorph; Organotin compounds such as fentin hydroxide and fentin acetate; urea compounds such as pensicuron; Carboxylic acid amide compounds such as dimethomorph, flumorph, pyrimorph, iprovalicarb, benthiavalicarb-isopropyl, mandipropamid; Phenylcarbamate compounds such as diethofencarb; cyanopyrrole compounds such as fludioxonil and fenpiclonil; strobilurin compounds such as azoxystrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin, pyraclostrobin, fluoxastrobin, enestroburin, pyraoxystrobin, pyrametostrobin, coumoxystrobin, enoxastrobin, phenaminestrobin, flufenoxystrobin, triclopyricarb, and mandestrobin; Oxazole compounds such as famoxadone and oxathiapiprolin; 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 and dodine; quinoline compounds such as tebufloquin, quinoxyfen, quinofumelin, and ipflufenoquin; Thiazolidine compounds such as flutianil; Carbamate compounds such as propamocarb hydrochloride, pyribencarb, and tolprocarb; tetrazole compounds such as picarbutrazox and metyltetraprole; Sulfonamide compounds such as amisulbrom and cyazofamid; 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 and florylpicoxamid; Sulfur, sulfur-based compounds such as lime sulfur; Other compounds include pyroquilon, diclomezine, chloropicrin, dazomet, metam-sodium, proquinazid, spiroxamine, and dipymetitrone; Microbial disinfectants such as Bacillus amyloliqefaciens strain QST713, Bacillus amyloliqefaciens strain FZB24, Bacillus amyloliqefaciens strain MBI600, Bacillus amyloliqefaciens strain D747, Pseudomonas fluorescens, Bacillus subtilis, and Trichoderma atroviride SKT-1; and Plant extracts such as tea tree oil.

[0161] Preferred embodiments of the present invention are as follows, but the present invention is not limited to these. [1] A nematicidal composition containing a compound represented by formula (I) or a salt thereof as an active ingredient. [2] A method for controlling nematodes, which comprises applying a nematicidal composition containing an effective amount of a compound represented by formula (I) or a salt thereof to soil, nematodes, or plants. [3] In the compound represented by formula (I) or a salt thereof, A is 1 to 5 R 1 is phenyl substituted with R 1 is halogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or haloalkoxy; R 1 If there are two R 1 together, one or two Z 1 The nematicidal composition according to [1] above, which is a compound or a salt thereof which may form a ring optionally substituted by: [4] In the compound represented by formula (I) or a salt thereof, A is 1 to 5 R1 is phenyl substituted with R 1 is halogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or haloalkoxy; R 1 If there are two R 1 together, one or two Z 1 The method for controlling nematodes according to [2] above, wherein the compound is a compound which may form a ring optionally substituted by the following formula (I) or a salt thereof. [5] A compound represented by formula (I) or a salt thereof. [6] A compound represented by formula (IA) or a salt thereof. [7] A compound represented by formula (IB) or a salt thereof. [8] R 1A The compound or salt thereof according to [6] above, wherein is halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, or (C1-C6)-haloalkoxy. [9] R 1A The compound or salt thereof according to [6] above, wherein is halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, or (C1-C6)-haloalkoxy.

[10] R 1A The compound or salt thereof according to [6] above, wherein is halogen, (C1-C6)-alkyl, or (C1-C6)-haloalkyl.

[11] Two R 1A together, one or two Z 1A The compound or salt thereof according to [6] above, which forms a ring optionally substituted with

[12] R 2A and R 3A The compound or salt thereof according to any one of [6] to

[11] above, wherein each of

[13] R 2A and R 3A The compound or salt thereof according to any one of [6] to

[11] above, wherein both are methyl.

[14] R 4AThe compound or salt thereof according to any one of [6] to

[13] above, wherein is halogen, (C1-C6)-haloalkyl, (C1-C6)-alkylsulfinyl, (C1-C6)-alkylsulfonyl, nitro, or cyano.

[15] R 4A The compound or salt thereof according to any one of [6] to

[13] above, wherein is fluorine, chlorine, bromine, difluoromethyl, trifluoromethyl, nitro, or cyano.

[16] R 6A The compound or salt thereof according to any one of [6] to

[15] above, wherein is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl.

[17] R 6A The compound or salt thereof according to any one of [6] to

[15] above, wherein

[18] The compound or salt thereof according to any one of [6] to

[17] above, wherein n is 1 or 2.

[19] n is 1 and one R 1A is substituted at the 2- or 3-position of the phenyl, or a salt thereof according to [6] or [8] to

[17] above.

[20] n is 1 and 1 R 1A is substituted at the 2-position of phenyl, or a salt thereof according to [6] or [8] to

[17] above.

[21] n is 1 and one R 1A is substituted at the 3-position of phenyl, or a salt thereof according to [6] or [8] to

[17] above.

[22] n is 2 and two R 1A is substituted at the 2- and 3-positions of the phenyl, or a salt thereof according to [6] or [8] to

[17] above.

[23] n is 2 and two R 1A is substituted at the 2- and 6-positions of the phenyl, or a salt thereof according to [6] or [8] to

[17] above.

[24] n is 2 and two R 1A is substituted at the 2- and 5-positions of the phenyl, or a salt thereof according to [6] or [8] to

[17] above.

[25] A method for controlling nematodes, which comprises applying a nematicidal composition containing an effective amount of the compound or salt thereof according to any one of [6] to

[24] above to soil, nematodes, or plants.

[26] A nematicide for agricultural and horticultural use, comprising the compound or salt thereof according to any one of [6] to

[24] above as an active ingredient.

[0162] The compound of the present invention is preferably a compound of formula (IA) or a compound of formula (IB), more preferably a compound of formula (IA). [Example]

[0163] Examples of the present invention will now be described, but the present invention is not limited to these.

[0164] Synthesis Example 1: Synthesis of N'-(2-methyl-1-phenyl-2-(3-trifluoromethyl-1H-pyrazol-1-yl)propylidene)formhydrazide (No. A-1) (1) Synthesis of 2-methyl-1-phenyl-2-(3-trifluoromethyl-1H-pyrazol-1-yl)propan-1-one Potassium carbonate (0.92 g) was added to a solution of 3-trifluoromethyl-1H-pyrazole (1.80 g) in acetonitrile (12 ml) and stirred at room temperature. After 30 minutes, 2-bromo-2-methyl-1-phenylpropan-1-one (3.01 g) was added and stirred at room temperature to obtain a mixture. After 10 minutes, the mixture was heated to 70°C and reacted for 20.5 hours to obtain a reaction mixture. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extracted solution was then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain the target product (1.23 g). 1 H NMR (CDCl3 / 300MHz):δ(ppm)= 7.50-7.40 (m, 2H), 7.35-7.23 (m, 4H), 6.57 (d, 1H), 1.93 (s, 6H).

[0165] (2) Synthesis of (2-methyl-1-phenyl-2-(3-trifluoromethyl-1H-pyrazol-1-yl)propylidene)hydrazide Hydrazine monohydrate (0.38 g) was added to a solution of 2-methyl-1-phenyl-2-(3-trifluoromethyl-1H-pyrazol-1-yl)propan-1-one (0.84 g) in ethanol (2.51 ml) and refluxed for 19.5 hours to obtain a reaction mixture. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The resulting extract was then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain the target product (0.37 g). 1 H NMR (CDCl3 / 300MHz):δ(ppm)= 7.45-7.42 (m, 1H), 7.37-7.28 (m, 3H), 6.70-6.62 (m, 2H), 6.45 (d, 1H), 5.10 (s, 2H), 1.82 (s, 6H).

[0166] (3) Synthesis of (N'-(2-methyl-1-phenyl-2-(3-trifluoromethyl-1H-pyrazol-1-yl)propylidene)formhydrazide (No. A-1) To a solution of (2-methyl-1-phenyl-2-(3-trifluoromethyl-1H-pyrazol-1-yl)propylidene)hydrazide (0.20 g) in ethyl formate (2 ml), formic acid (0.04 g) was added and refluxed for 2 hours to obtain a reaction mixture. Water was added to the reaction mixture, and then saturated aqueous sodium bicarbonate was used to obtain an alkaline reaction solution. The reaction solution was extracted with ethyl acetate, and the resulting extract was concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain the target product (No. A-1, 0.20 g). 1 H NMR (CDCl3 / 300MHz):δ(ppm)= 8.73 (d, 1H), 8.03 (d, 1H), 7.43-7.29 (m, 4H), 6.67-6.61 (m, 2H), 6.45 (d, 1H), 1.89 (s, 6H).

[0167] Synthesis Example 2: Synthesis of two geometric isomers (No. B-1 and No. B-2) of N'-(phenyl(1-(3-trifluoromethyl-1H-pyrazol-1-yl)cyclopropyl)methylene)formhydrazide (1) Synthesis of 2-bromo-4-chloro-1-phenylbutan-1-one Trimethylphenylammonium tribromide (1.28 g) was added to a solution of 4-chloro-1-phenylbutan-1-one (0.61 g) in tetrahydrofuran (6.07 ml) and the mixture was allowed to react at room temperature for 15.5 hours to obtain a reaction mixture. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The resulting extract was then concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain the target product (0.86 g). 1 H NMR (CDCl3 / 300MHz):δ(ppm)= 8.08-8.01 (m, 2H), 7.66-7.59 (m, 1H), 7.55-7.48 (m, 2H), 5.49 (dd, 1H), 3.90-3.72 (m, 2H), 2.67-2.49 (m, 2H).

[0168] (2) Synthesis of phenyl(1-(3-trifluoromethyl-1H-pyrazol-1-yl)cyclopropyl)methanone Potassium carbonate (0.51 g) was added to a solution of 3-trifluoromethyl-1H-pyrazole (0.50 g) in acetonitrile (2.58 ml) and stirred at room temperature. After 50 minutes, 2-bromo-4-chloro-1-phenylbutan-1-one (0.86 g) was added, the temperature was raised to 90 °C, and the reaction was continued for 6 hours to obtain a reaction mixture. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The resulting extract was concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain the target product (0.86 g). 1H NMR (CDCl3 / 300MHz):δ(ppm)= 7.48-7.39 (m, 4H), 7.32-7.24 (m, 2H), 6.43 (d, 1H), 2.08-2.01 (m, 2H), 1.89-1.83 (m, 2H).

[0169] (3) Synthesis of two geometric isomers of (phenyl(1-(3-trifluoromethyl-1H-pyrazol-1-yl)cyclopropyl)methylene)hydrazide Hydrazine monohydrate (0.51 g) was added to a solution of phenyl(1-(3-trifluoromethyl-1H-pyrazol-1-yl)cyclopropyl)methanone (1.07 g) in ethanol (4.29 ml), and the mixture was refluxed for 25.5 hours to obtain a reaction mixture. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The resulting extract was concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain the main product (0.41 g) and its geometric isomer (0.23 g). main product 1 H NMR (CDCl3 / 300MHz):δ(ppm)= 7.41-7.29 (m, 4H), 7.11-7.03 (m, 2H), 6.33 (d, 1H), 5.15 (s, 2H), 1.65-1.58 (m, 2H), 1.56-1.49 (m, 2H). Geometric isomer of the main product 1 H NMR (CDCl3 / 300MHz):δ(ppm)= 7.80-7.74 (m, 2H), 7.72-7.68 (m, 1H), 7.40-7.27 (m, 3H), 6.64 (s, 2H). 6.50 (d, 1H), 1.92-1.86 (m, 2H), 1.41-1.35 (m, 2H).

[0170] (4) Synthesis of two geometric isomers (No. B-1 and No. B-2) of N'-(phenyl(1-(3-trifluoromethyl-1H-pyrazol-1-yl)cyclopropyl)methylene)formhydrazide To a solution of (phenyl(1-(3-trifluoromethyl-1H-pyrazol-1-yl)cyclopropyl)methylene)hydrazide (0.20 g) in ethyl formate (2.01 ml), formic acid (0.05 g) was added and refluxed for 2.5 hours to obtain a reaction mixture. Water was added to the reaction mixture, and then saturated aqueous sodium bicarbonate was used to obtain an alkaline reaction solution. The reaction solution was extracted with ethyl acetate, and the resulting extract was concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain the main product (No. B-1, 0.18 g) and its geometric isomer (No. B-2, 0.02 g). main product 1 H NMR (CDCl3 / 300MHz):δ(ppm)= 8.61 (d, 1H), 8.17 (d, 1H), 7.43-7.37 (m, 3H), 7.37-7.34 (m, 1H), 7.06-6.99 (m, 2H), 6.33 (d, 1H), 1.80-1.61 (m, 4H). Geometric isomer of the main product 1 H NMR (CDCl3 / 300MHz):δ(ppm)= 10.67 (d, 1H), 8.84 (d, 1H), 7.93-7.86 (m, 2H), 7.74-7.70 (m, 1H), 7.46-7.38 (m, 3H), 6.55 (d, 1H), 1.96-1.89 (m, 2H), 1.45-1.38 (m, 2H).

[0171] Synthesis Example 3: Synthesis of N'-(2-methyl-1-(3-methylphenyl)-2-(3-trifluoromethyl-1H-triazol-1-yl)propylidene)formhydrazide (No. A-323) (1) Synthesis of (2-methyl-1-(3-methylphenyl)-propylidene)hydrazone A mixture prepared using 2-methyl-1-(3-methylphenyl)-propan-1-one (0.35 g), ethanol (1.05 mL), and hydrazine monohydrate (0.27 g) was degassed and then refluxed for 13.5 hours to obtain a reaction mixture. The reaction mixture was diluted with ethyl acetate and heptane and filtered through a pad containing Celite and silica gel to obtain a filtrate. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain the target product (0.35 g). 1 H NMR (CDCl3 / 500MHz):δ(ppm)= 7.34 (t, 1H), 7.18 (d, 1H), 6.98 (s, 1H), 6.97 (d, 1H), 4.93 (brs, 2H), 2.71 (m, 1H), 2.38 (s, 3H), 1.09 (d, 6H).

[0172] (2) Synthesis of N'-(2-methyl-1-(3-methylphenyl)-propylidene)formhydrazide A mixture of (2-methyl-1-(3-methylphenyl)-propylidene)hydrazone (0.35 g), ethyl formate (1.4 mL), and formic acid (0.12 g) was purged with nitrogen and refluxed for 5 hours to obtain a reaction solution. The reaction solution was concentrated under reduced pressure and purified by column chromatography (eluent: ethyl acetate / heptane) to obtain the target product (0.29 g). 1 H NMR (CDCl3 / 500MHz):δ(ppm)= 8.70 (d, 1H), 8.22 (d, 1H), 7.36 (t, 1H), 7.24 (d, 1H), 6.90 (s, 1H), 6.90 (d, 1H), 2.78 (m, 1H), 2.39 (s, 3H), 1.13 (d, 6H).

[0173] (3) Synthesis of N'-(2-chloro-2-methyl-1-(3-methylphenyl)-propylidene)formhydrazide A mixture prepared using N'-(2-methyl-1-(3-methylphenyl)-propylidene)formhydrazide (0.26 g), toluene (2.5 mL), and sulfuryl chloride (0.2 g) was stirred at room temperature for 4 hours to obtain a reaction mixture. The obtained reaction mixture was cooled with ice and then ice water and saturated aqueous sodium bicarbonate solution were added successively, followed by stirring, and extracted three times with ethyl acetate. The organic layer obtained by extraction was filtered through a Celite pad to obtain a filtrate. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain the target product (0.24 g). 1 H NMR (CDCl3 / 500MHz):δ(ppm)= 8.70 (d, 1H), 8.05 (d, 1H), 7.39 (t, 1H), 7.29 (d, 1H), 7.03 (s, 1H), 7.03 (d, 1H), 2.41 (s, 3H), 1.82 (s, 6H).

[0174] (4) Synthesis of N'-(2-methyl-1-(3-methylphenyl)-2-(3-trifluoromethyl-1H-triazol-1-yl)propylidene)formhydrazide (No. A-323) A mixture prepared using 3-trifluoromethyl-1H-triazole (0.05 g), DMF (0.3 mL), and potassium carbonate (0.05 g) was purged with nitrogen and stirred overnight at room temperature. A solution of N-(2-chloro-2-methyl-1-(3-methylphenyl)-propylidene)formhydrazide (0.07 g) in DMF (0.3 mL) was added dropwise to the stirred mixture and stirred at room temperature for 1 hour to obtain a reaction mixture. The resulting reaction mixture was diluted with water and extracted three times with ethyl acetate / heptane. The organic layer obtained from the extraction was filtered through a Celite pad to obtain the filtrate. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (eluent: ethyl acetate / heptane) to obtain the desired product (No. A-323, 0.09 g). 1H NMR (CDCl3 / 500MHz):δ(ppm)= 8.68 (d, 1H), 8.04 (d, 1H), 8.03 (s, 1H), 7.28 (t, 1H), 7.22 (d, 1H), 6.55 (d, 1H), 6.49 (s, 1H), 2.28 (s, 3H), 1.94 (s, 6H).

[0175] Next, representative examples of Compound (I) of the present invention are specifically listed in Tables 1 and 2. These compounds can be synthesized based on the above-mentioned production methods and synthesis examples, as well as methods known in the art.

[0176] In each table, No. indicates the compound No. In Tables 1 and 2, compounds listed as NMR in the physical properties column are listed as NMR in Tables 3 and 4. 1 H-NMR spectral data are shown. Furthermore, when the compounds described in Tables 1 and 2 are salts of Compound (I) of the present invention, the type of the salt is also shown in the physical properties column in Tables 1 and 2.

[0177] Each A and R in Tables 1 and 2 2 , R 3 , R 4 , R 6 The abbreviations used in the , and X columns are as follows: Me is a methyl group, Et is an ethyl group, nPr is a normal propyl group, iPr is an isopropyl group, cPr is a cyclopropyl group, tBu is a tertiary butyl group, cBu is a cyclobutyl group, nHexyl is a normal hexyl group, cHexyl is a cyclohexyl group, Ph is a phenyl group, Na salt is a sodium salt, K salt is a potassium salt, di is two, bis is two, and tri is three.

[0178] In Tables 1 and 2, R 5 The compound (I) of the present invention is represented by the formula (I) in which A and R in Tables 1 and 2 are CHO. 4 The position of each substituent shown in the column indicates the position of the substituent as follows: "*" indicates the bond position.

[0179] [ka]

[0180] For example, the compound described as "4-Cl-Ph" in column A has one R at the substituent position assigned to A (phenyl) in the chemical structure above. 1 This indicates that the compound is substituted with a chloro group, that is, only the 4-position of the phenyl is substituted with a chloro group. Also, R 4 The compound with "3-CF3" in the column and "1" in the m column has one R at the substituent position on the five-membered heterocyclic ring in the above chemical structure. 4 R represents a compound substituted with a trifluoromethyl group, i.e., a compound in which only the 3-position of the 5-membered heterocyclic ring is substituted with a trifluoromethyl group. 4 The compound described as "3-CF3-5-Me" in the column and "2" in the m column has two R groups at the substituent positions on the five-membered heterocyclic ring in the above chemical structure. 4 R represents a compound substituted with a trifluoromethyl group at the 3-position of the five-membered heterocyclic ring and a methyl group at the 5-position of the five-membered heterocyclic ring. 4 The compounds described as "-" in the column and "0" in the column m have R at the 3rd and 5th positions of the five-membered hetero ring in the above chemical structure. 4 represents that the group is unsubstituted.

[0181] Compound Nos. A-188, A-189, B-186, and B-187 listed in Tables 1 and 2 are sodium salts of A-1, A-2, B-1, and B-3, respectively, and compound Nos. A-190, A-191, B-188, and B-189 are potassium salts of A-1, A-2, B-1, and B-3, respectively.

[0182] In Tables 3 and 4 1 In H-NMR data, s indicates singlet, brs indicates broad singlet, d indicates doublet, t indicates triplet, q indicates quartet, dd indicates double doublet, dt indicates double triplet, ddd indicates double double doublet, and m indicates multiplet.

[0183] Table 1

[0184] Table 2

[0185] Table 3

[0186] Table 4

[0187] Table 5

[0188] Table 6

[0189] Table 7

[0190] Table 8

[0191] Table 9

[0192] Table 10

[0193] Table 11

[0194] Table 12

[0195] Table 13

[0196] Table 14

[0197] Table 15

[0198] Table 16

[0199] Table 17

[0200] Table 18

[0201] Table 19

[0202] Table 20

[0203] Table 21

[0204] Table 22

[0205] Table 23

[0206] Table 24

[0207] Table 25

[0208] Table 26

[0209] Table 27

[0210] Table 28

[0211] Table 29

[0212] [Table 30]

[0213] [Table 31]

[0214] [Table 32]

[0215] [Table 33]

[0216] [Table 34]

[0217] [Table 35]

[0218] [Table 36]

[0219] [Table 37]

[0220] Test example 1: Efficacy test against sweet potato root-knot nematodes 200 mL of soil contaminated with sweet potato root-knot nematodes was irrigated with 10 mL of this composition, which had been prepared using water to give a compound (I) concentration of 400 ppm or 200 ppm, and then mixed to ensure uniform dispersion. The treated soil was packed into pots, after which three cucumber seeds were sown and the pots were placed in a greenhouse. Two to three weeks after sowing the cucumber seeds, the degree of root gall formation on the roots was assessed according to the root gall index shown in Table 5. As a result, the compounds Nos. A-1, A-2, A-89, A-90, A-94, A-95, A-96, A-107, A-150, A-151, A-152, A-156, A-157, A-160, A-161, A-193, A-195, A-198, A-199, A-200, A-201, A-202, A-203, A-205, A-206, A-216, A-217, A-218, A-219, A-300, A-301, A-302, A-303, A-304, A-305, A-306, A-307, A-308, A-310, A-311, A-312, A-313, A-314, A-315, A-316, A-317, A-318, A-319, A-409, A-420, A-421, A-422, A-423, A-424, A-425, A-426, A-427, A-428, A-429, A-509, A-510, A-520, A-521, A-522, A-523, A-524, A-525, A-530, A-531, A-532, A-533, A-534, A-535, A-536, A-537, A-540, A-541, A-542, A-543, A-544, A-545, A-546, A-547, A-548, A-549, A 217, A-224, A-233, A-234, A-235, A-240, A-241, A-244, A-245, A-247, A-248, A-249, A-251, A-252 , A-253, A-255, A-256, A-257, A-260, A-261, A-264, A-265, A-270, A-271, A-272, A-273, A-274, A-2 75, A-277, A-278, A-279, A-318, A-319, A-322, A-323, A-324, A-327, A-328, A-329, A-330, A-332, A-333, A-334, A-335, A-336, A-337, A-344, A-349, A-350, A-351, A-352, A-410, A-411, A-412, A-41 Each composition containing compound No. 3, A-414, A-416, A-417, A-419, A-424, A-430, B-1, B-2, B-3, B-4, B-81, B-87, B-105, B-106, B-148, B-190, B-192 or B-196 showed a high control effect with a root-club index of 1 or less at 400 ppm, and a composition containing compound No. A-153 showed a high control effect with a root-club index of 1 or less at 200 ppm.

[0221] [Table 38]

[0222] Test example 2: Efficacy test against root-lesion nematodes 10 mL of this composition, prepared by adjusting the concentration of compound (I) using water to 800 ppm, was irrigated into 200 mL of soil contaminated with the root-lesion nematode, and then mixed to ensure uniform dispersion. The treated soil was filled into pots, after which three burdock seeds were sown and placed in a greenhouse. Approximately one month after sowing the burdock seeds, the extent of damage to the roots was evaluated according to the damage index shown in Table 6. As a result, each composition containing compound No. A-1, A-318, B-1, or B-192 showed a high control effect with a damage index of 1 or less.

[0223] [Table 39]

[0224] Test example 3: Efficacy test against soybean cyst nematodes 10 mL of the composition, prepared by adjusting the concentration of Compound (I) using water to 800 ppm or 400 ppm, was irrigated into 200 mL of soybean cyst nematode-infested soil, and then mixed to ensure uniform dispersion. The treated soil was filled into pots, after which three soybean seeds were sown and placed in a greenhouse. Approximately one month after sowing the soybean seeds, the degree of cyst infestation in the roots was determined according to the infestation index shown in Table 7. As a result, each composition containing compound No. A-1, A-2, A-89, A-91, A-107, A-109, A-271, A-274, A-279, A-318, A-319, A-322, A-323, A-328, A-333, A-352, A-411, A-416, B-1, B-3, B-4, B-6, B-24, B-192 or B-196 showed a high control effect with an infestation index of 1 or less at 800 ppm, and a composition containing compound No. A-260, B-106 or B-193 showed a high control effect with an infestation index of 1 or less at 400 ppm.

[0225] [Table 40]

[0226] Next, the effects of this composition and a composition containing the compound described in WO 2020 / 179910 on sweet potato root-knot nematodes will be shown in the following comparative test.

[0227] Comparative Test Compounds A-1, A-2, and A-318 were used as the active ingredients of this composition, and compounds A-1, A-3, and A-58 described in International Publication No. 2020 / 179910 were used as comparative active ingredients. Except for adjusting the active ingredient concentration to 50 ppm, the effectiveness test against sweet potato root-knot nematodes was conducted in the same manner as in Test Example 1 above. The test results are shown in Tables 8 and 9. As a result of the test, each composition containing the compound described in WO 2020 / 179910 (compound No. A-1, A-3, or A-58) had a root-knot index of 2. In contrast, each composition containing the compound of the present invention (compound No. A-1, A-2, or A-318) had a root-knot index of 1 or 0. A root-knot index of 2 indicates that the ratio of healthy roots is 50% or less, and the control effect is limited to the point where the test crop (cucumber) cannot grow healthily.In contrast, a root-knot index of 1 or 0 indicates that the ratio of healthy roots is 75% or more, and the control effect is high, allowing the cucumber to grow healthily.

[0228] [Table 41]

[0229] [Table 42]

[0230] The formulation of the present composition will be specifically explained below, but the blending ratio, dosage form, etc. are not limited to the following formulation examples.

[0231] Next, formulation examples are described. Formulation Example 1 (1) Compound (I) 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 alkylnaphthalene sulfonate 2 parts by weight The above ingredients are mixed uniformly to prepare a wettable powder.

[0232] Formulation Example 2 (1) Compound (I) 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 prepare a powder.

[0233] Formulation Example 3 (1) Compound (I) 20 parts by weight (2) N,N-dimethylacetamide 20 parts by weight (3) Polyoxyethylene tristyryl phenyl ether 10 parts by weight (4) Calcium dodecylbenzenesulfonate 2 parts by weight (5) Xylene 48 parts by weight The above ingredients are mixed and dissolved uniformly to form an emulsion.

[0234] Formulation Example 4 (1) Clay 68 parts by weight (2) Sodium lignosulfonate 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) White carbon 25 parts by weight The mixture of the above components and compound (I) are mixed in a weight ratio of 4:1 to prepare a wettable powder.

[0235] Formulation Example 5 (1) Compound (I) 50 parts by weight (2) Sodium alkylnaphthalenesulfonate formaldehyde condensate 2 parts by weight (3) Silicone oil 0.2 parts by weight (4) Water 47.8 parts by weight The above ingredients are mixed uniformly and crushed into a liquid. (5) Sodium polycarboxylate 5 parts by weight (6) 42.8 parts by weight of anhydrous sodium sulfate Add the ingredients, mix evenly, granulate, and dry to make a water dispersible granule.

[0236] Formulation Example 6 (1) Compound (I) 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene alkyl ether phosphate ester 0.1 parts by weight (4) Granular calcium carbonate 93.9 parts by weight (1) to (3) are mixed uniformly in advance, diluted with an appropriate amount of acetone, and then sprayed onto (4). The seton is removed to give granules.

[0237] Formulation Example 7 (1) Compound (I) 2.5 parts by weight (2) N,N-dimethylacetamide 2.5 parts by weight (3) Soybean oil 95 parts by weight The above ingredients are mixed and dissolved uniformly to make an ultra low volume formulation.

[0238] Formulation Example 8 (1) Compound (I) 40 parts by weight (2) Potassium polyoxyethylene tristyryl phenyl ether phosphate 4 parts by weight (3) Silicone oil 0.2 parts by weight (4) Xanthan gum 0.1 parts by weight (5) Ethylene glycol 5 parts by weight (6) Water 50.7 parts by weight The above ingredients are mixed uniformly and pulverized to prepare an aqueous suspension.

[0239] Formulation Example 9 (1) Compound (I) 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 prepare a liquid preparation.

[0240] In addition, the entire contents of the specification, claims, and abstract of Japanese Patent Application No. 2021-113233, filed on July 8, 2021, are hereby incorporated by reference as part of the disclosure of the specification of the present invention.

Claims

1. Formula (I): 【Chemistry 1】 wherein X is N, CH or CR ４ and A is unsubstituted phenyl or 1 to 5 R １ is a phenyl substituted with R １ is halogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or haloalkoxy; R １ If there are two R １ together, one or two Z １ may form a ring which may be substituted with Z １ is halogen or alkyl, R ２ and R ３ are each alkyl, or R ２ and R ３ Together, (C ３ -C ６ )-forms a carbocyclic ring, R ４ is halogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro or cyano; R ５ is CHO, R ６ is H, -SO ２ CF ３ , -C(=O)OZ ３ , alkyl, alkenyl, alkynyl or alkoxyalkyl, or Z ２ is an aralkyl optionally substituted with Z ２ is an alkoxy; Z ３ is Z ２ aralkyl or alkyl optionally substituted with and m is an integer of 0 to 2] or a salt thereof as an active ingredient.

2. Formula (I): 【Chemistry 2】 wherein X is N, CH or CR ４ and A is unsubstituted phenyl or 1 to 5 R １ is a phenyl substituted with R １ is halogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or haloalkoxy; R １ If there are two R １ together, one or two Z １ may form a ring which may be substituted with Z １ is halogen or alkyl, R ２ and R ３ are each alkyl, or R ２ and R ３ Together, (C ３ -C ６ )-forms a carbocyclic ring, R ４ is halogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro or cyano; R ５ is CHO, R ６ is H, -SO ２ CF ３ , -C(=O)OZ ３ , alkyl, alkenyl, alkynyl or alkoxyalkyl, or Z ２ is an aralkyl optionally substituted with Z ２ is an alkoxy; Z ３ is Z ２ aralkyl or alkyl optionally substituted with and m is an integer of 0 to 2], or a salt thereof.

3. The following formula: 【Transformation 3】 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 A compound selected from the group consisting of:

4. In the compound represented by formula (I) or a salt thereof, A is 1 to 5 R １ phenyl substituted with R １ is halogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or haloalkoxy; R １ If there are two R １ together, one or two Z １ 2. The nematicidal composition according to claim 1, which is a compound which may form a ring optionally substituted by the following formula: or a salt thereof.

5. In the compound represented by formula (I) or a salt thereof, A is 1 to 5 R １ phenyl substituted with R １ is halogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or haloalkoxy; R １ If there are two R １ together, one or two Z １ 3. The method for controlling nematodes according to claim 2, wherein the compound is a compound which may form a ring optionally substituted by the following formula (I) or a salt thereof.

6. Formula (IA): 【Chemistry 26】 wherein X is N, CH or CR ４Ａ and R １Ａ is halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl, (C ３ -C ６ )-cycloalkyl, (C １ -C ６ )-alkoxy, or (C １ -C ６ )-haloalkoxy, and R １Ａ If there are two R １Ａ together, one or two Z １Ａ may form a ring which may be substituted with Z １Ａ is a halogen, or (C １ -C ６ )-alkyl, R ２Ａ and R ３Ａ are respectively (C １ -C ６ )-alkyl or R ２Ａ and R ３Ａ Together, (C ３ -C ６ )-forms a carbocyclic ring, R ４Ａ is halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl, (C ３ -C ６ )-cycloalkyl, (C １ -C ６ )-alkoxy, (C １ -C ６ )-haloalkoxy, (C １ -C ６ )-alkylthio, (C １ -C ６ )-alkylsulfinyl, (C １ -C ６ )-alkylsulfonyl, nitro or cyano; R ６Ａ is H, -SO ２ CF ３ , -C(=O)OZ ３Ａ , (C １ -C ６ )-alkyl, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl or (C １ -C ６ )-alkoxy-(C １ -C ６ )-alkyl, or Z ２Ａ (C ７ -C １２ )-aralkyl, Z ２Ａ (C １ -C ６ )-alkoxy, Z ３Ａ is Z ２Ａ (C ７ -C １２ )-aralkyl, or (C １ -C ６ )-alkyl, n is an integer from 1 to 5; and m is an integer of 0 to 2, or a salt thereof.

7. Formula (IB): 【Chemistry 27】 wherein X is N, CH or CR ４Ａ and R ２Ａ and R ３Ａ are respectively (C １ -C ６ )-alkyl or R ２Ａ and R ３Ａ Together, (C ３ -C ６ )-forms a carbocyclic ring, R ４Ａ is halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl, (C ３ -C ６ )-cycloalkyl, (C １ -C ６ )-alkoxy, (C １ -C ６ )-haloalkoxy, (C １ -C ６ )-alkylthio, (C １ -C ６ )-alkylsulfinyl, (C １ -C ６ )-alkylsulfonyl, nitro or cyano; R ６Ａ is H, -SO ２ CF ３ , -C(=O)OZ ３Ａ , (C １ -C ６ )-alkyl, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl or (C １ -C ６ )-alkoxy-(C １ -C ６ )-alkyl, or Z ２Ａ (C ７ -C １２ )-aralkyl, Z ２Ａ (C １ -C ６ )-alkoxy, Z ３Ａ is Z ２Ａ (C ７ -C １２ )-aralkyl, or (C １ -C ６ )-alkyl, and m is an integer of 0 to 2, or a salt thereof.

8. In the compound represented by formula (IA) or a salt thereof, R １Ａ is halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl, (C ３ -C ６ )-cycloalkyl, (C １ -C ６ )-alkoxy, or (C １ -C ６ 7. The compound or salt thereof according to claim 6, wherein the alkoxy group is 2-haloalkoxy.

9. In the compound represented by formula (IA) or a salt thereof, R ２Ａ and R ３Ａ Each (C １ -C ３ 7. The compound or salt thereof according to claim 6, wherein the aryl group is 2-alkyl.

10. In the compound represented by formula (IA) or a salt thereof, R ４Ａ is halogen, (C １ -C ６ )-haloalkyl, (C １ -C ６ )-alkylsulfinyl, (C １ -C ６ 7. The compound or salt thereof according to claim 6, wherein the aryl group is aryl, arylsulfonyl ...

11. In the compound represented by formula (IB) or a salt thereof, R ２Ａ and R ３Ａ Each (C １ -C ３ 8. The compound or salt thereof according to claim 7, wherein R is 1 or 2. 9.)-alkyl.

12. In the compound represented by formula (IB) or a salt thereof, R ４Ａ is halogen, (C １ -C ６ )-haloalkyl, (C １ -C ６ )-alkylsulfinyl, (C １ -C ６ 8. The compound or salt thereof according to claim 7, wherein the aryl group is arylsulfonyl, ...

13. A method for controlling nematodes, which comprises applying a nematicidal composition containing an effective amount of the compound or salt thereof according to claim 6 or 7 to soil, nematodes or plants.

14. 8. A nematicide for agricultural and horticultural use, comprising the compound or salt thereof according to claim 6 or 7 as an active ingredient.

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