Triazinyl-fused ring carboxamide derivatives and their nematicidal use

Abstract

The present invention relates to a compound with excellent nematicidal effect, a method for producing the same, a nematicidal formulation containing the compound as an active ingredient, and a method for controlling nematodes, comprising applying the compound to plants or soil. In particular, the compound of the present invention is useful for controlling root-knot nematodes (Meloidogyne spp.), cyst nematodes (Heterodera spp., Globodera spp.), root-rot nematodes (Pratylenchus spp.), Rotylenchus spp., etc.

Description

[Technical Field]

[0001] This application claims priority based on Korean Patent Application No. 10-2022-0092756, filed on July 26, 2022, the entire contents of which are incorporated herein by reference in their entirety in the specification and drawings thereof.

[0002] The present disclosure relates to compounds of specific structures that have nematicidal effects. The present disclosure also relates to the use of the compounds of the present disclosure for controlling nematodes. That is, the present disclosure relates to a nematicidal composition containing a compound according to the present disclosure. The present disclosure also relates to a method for controlling nematodes, characterized by applying a compound according to the present disclosure. [Background technology]

[0003] Nematodes cause considerable losses in agricultural produce. Chemical compounds with nematicidal activity are widely used to eliminate these nematodes. Nematicidal compounds must be highly active to be agriculturally useful, have broad-spectrum activity against various strains of nematodes, and not be toxic to non-target organisms.

[0004] Furthermore, conventional anthelmintics have been plagued by widespread resistance among parasitic nematodes, resulting in the continued problem of nematodes in livestock.

[0005] On the other hand, Patent Document 1 discloses a triazine heterocyclic compound having a nematicidal effect, but the compound disclosed in Patent Document 1 does not exhibit a sufficient nematicidal effect.

[0006] Thus, there is a continuing need for more effective, cheaper, less toxic, environmentally safer, or nematicidal compounds that have a different mode of action. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] International Publication No. WO2016 / 116058 Summary of the Invention [Problem to be solved by the invention]

[0008] The problem to be solved by the present invention is therefore to provide compounds that can be used as nematicides with high selectivity and high compatibility, which have sufficient or improved nematicidal activity at relatively low application rates.

[0009] Another problem that the present invention aims to solve is to provide a nematicidal use of the compounds according to the present disclosure.

[0010] A further problem to be solved by the present invention is to provide a nematicidal composition containing the compound according to the present disclosure as an active ingredient.

[0011] A further problem to be solved by the present invention is to provide a method for controlling nematodes, which comprises applying a compound according to the present disclosure. [Means for solving the problem]

[0012] In order to solve the above problems, the present invention provides a compound represented by the following chemical formula I or an agronomically acceptable salt thereof:

[0013] [Chemical formula I] [ka] In Formula I, Y is

[0014] [ka] where W is CH or N, Q1 is CF3 or halogen, and Q2 is hydrogen, halogen, methyl, or CF3; R1, R2, R3 and R4 are each independently hydrogen, (C1-C6) alkyl, (C1-C3) haloalkyl or phenyl, or R1 and R2 or R3 and R4 are linked together to form a (C3-C6) cycloalkyl; X is O or S; A is a benzene or pyridine fused to the triazine ring on the right, Z is hydrogen, halogen, cyano, -CH=NO-R', SR', S(O)R', NR'R", (C1-C6)alkyl, (C1-C3)haloalkyl, (C1-C6)alkoxy, (C1-C3)haloalkoxy, substituted or unsubstituted amine, substituted or unsubstituted (C3-C6)cycloalkyl, substituted or unsubstituted hetero(C3-C6)cycloalkyl, substituted or unsubstituted phenyl, where the substitution is with one or more groups selected from the group consisting of hydrogen, -OH, halogen, (C1-C6)alkyl, (C1-C3)haloalkyl, (C1-C6)alkoxy, and (C1-C3)haloalkoxy; R' and R" are each independently hydrogen, (C1-C6) alkyl, or (C1-C3) haloalkyl.

[0015] In one aspect of the present invention, the present invention provides a compound of formula I above, Y is

[0016] [ka] where Q2 is hydrogen, halogen, methyl or CF3; R1, R2, R3 and R4 are each independently hydrogen, (C1-C6) alkyl, (C1-C3) haloalkyl or phenyl, or R1 and R2 or R3 and R4 are linked together to form a (C3-C6) cycloalkyl; X is O, A is a benzene fused to a triazine ring on the right, Z is hydrogen, halogen, cyano, -CH=NO-R', SR', S(O)R', NR'R", (C1-C6)alkyl, (C1-C3)haloalkyl, (C1-C6)alkoxy, (C1-C3)haloalkoxy, substituted or unsubstituted amine, substituted or unsubstituted (C3-C6)cycloalkyl, substituted or unsubstituted hetero(C3-C6)cycloalkyl, substituted or unsubstituted phenyl, where the substitution is with one or more groups selected from the group consisting of hydrogen, -OH, halogen, (C1-C6)alkyl, (C1-C3)haloalkyl, (C1-C6)alkoxy, and (C1-C3)haloalkoxy; R' and R" are, independently of each other, hydrogen, (C1-C6) alkyl, or (C1-C3) haloalkyl; The present invention provides a compound or a pesticide-acceptable salt thereof.

[0017] In a preferred embodiment of the present invention, the present invention provides a compound of formula I above, Y is

[0018] [ka] and R1, R2, R3 and R4 are each independently hydrogen, (C1-C3) alkyl or phenyl, or R1 and R2 or R3 and R4 are linked together to form a (C3-C6) cycloalkyl; X is O, A is a benzene fused to a triazine ring on the right, Z is halogen, -CH=NO-R', (C1-C3)haloalkyl, (C1-C6)alkoxy, (C1-C3)haloalkoxy, substituted or unsubstituted amine, substituted or unsubstituted (C3-C6)cycloalkyl, substituted or unsubstituted hetero(C3-C6)cycloalkyl, substituted or unsubstituted phenyl, where the substitution is with one or more groups selected from the group consisting of hydrogen, -OH, halogen, (C1-C6)alkyl, (C1-C3)haloalkyl, (C1-C6)alkoxy, and (C1-C3)haloalkoxy; R' is hydrogen, (C1-C6) alkyl, or (C1-C3) haloalkyl; The present invention provides a compound or a pesticide-acceptable salt thereof.

[0019] In a further preferred embodiment of the present invention, the present invention provides a compound of formula I above, Y is

[0020] [ka] and R1, R2, R3 and R4 are each independently hydrogen, (C1-C3) alkyl or phenyl, or R1 and R2 or R3 and R4 are linked together to form a (C3-C6) cycloalkyl; X is O, A is a benzene fused to a triazine ring on the right, Z is halogen, (C1-C3)haloalkyl, or (C1-C6)alkoxy; The present invention provides a compound or a pesticide-acceptable salt thereof.

[0021] If a substituent is described as "optionally substituted" or "optionally substituted," the substituent can be (1) unsubstituted or (2) substituted with one or more of the defined substituents. If a substitutable position is unsubstituted, the default substituent is hydrogen.

[0022] As used herein, "halogen" and "halo" refer to fluorine, chlorine, bromine, or iodine.

[0023] As used herein, "(C1-C6) alkyl" refers to a saturated, straight-chain or branched acyclic hydrocarbon having 1 to 6 carbon atoms, such as methyl, ethyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 3-methyl-1-propynyl, 2-methyl-3-propynyl, pentynyl, or 1-hexynyl.

[0024] As used herein, "C 1-6 When written as ", ", "C1-6," "C1-C6," or "C1-C6," this means that the number of carbon atoms is 1 to 6. For example, (C1-C6) alkyl means alkyl having 1 to 6 carbon atoms.

[0025] As used herein, "(C3-C6)cycloalkyl" refers to, for example, cyclopropynyl, cyclobutynyl, cyclopentanyl, or cyclohexanyl.

[0026] As used herein, "(C1-C3)haloalkyl" refers to an alkyl having 1 to 3 carbon atoms in which one or more hydrogen atoms have been replaced with halogen atoms. For example, chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 1,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl.

[0027] As used herein, "(C1-C6)alkoxy" refers to -O-(alkyl), where alkyl is as defined above, for example, methoxy, ethoxy, n-propoxy, 1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy), 1,1-dimethylethoxy (tert-butoxy), pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpent ... Examples of methylpropoxy include 1,1-dimethylbutoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy.

[0028] As used herein, "(C1-C3)haloalkoxy" refers to an alkoxy in which one or more hydrogen atoms are replaced by halogen atoms, such as OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, -OC2F5, 2- Examples include fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH—C—F, OCF—C—F, 1-(CHF)-2-fluoroethoxy, 1-(CHCl)-2-chloroethoxy, or 1-(CHBr)-2-bromoethoxy.

[0029] As used herein, "hetero(C3-C6)cycloalkyl" refers to a saturated 3- to 6-membered monocyclic ring containing 1 to 4 heteroatoms independently selected from nitrogen, oxygen, and sulfur, wherein the nitrogen and sulfur heteroatoms can be optionally oxidized and the nitrogen heteroatom can be optionally quaternized. For example, "hetero(C3-C6)cycloalkyl" includes oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, azirididine, azetidine, pyrrolidine, piperidine, piperazine, pyrrolidinone, hydantoin, valerolactam, thiirane, thietane, tetrahydrothiophene, tetrahydrothiopyran, morpholine, tetrahydropyridine, tetrahydropyrimidine, and the like.

[0030] In the present invention, "pesticidally acceptable salts" include salts of active compounds prepared from relatively non-toxic acids and bases, depending on the specific substituents found in the compounds referred to herein. When a compound of the present invention contains a relatively acidic functionality, a base addition salt can be obtained by contacting the neutral form of such a compound with a sufficient amount of the desired base, pure or in a suitable inert solvent. Examples of pesticide-approved base addition salts include sodium, potassium, calcium, lithium, ammonium, trimethylammonium, organic amino, or magnesium salts, or similar salts. When a compound of the present invention contains a relatively basic functionality, an acid addition salt can be obtained by contacting the neutral form of such a compound with a sufficient amount of the desired acid, pure or in a suitable inert solvent. Examples of pesticide-acceptable acid addition salts include hydrochloride, hydrobromide, nitric acid, carbonic acid, monohydrogencarbonic acid, phosphoric acid, monohydrogenphosphate, dihydrogenphosphate, sulfuric acid, monohydrogen sulfate, hydrogen iodide, or phosphorous acid and the like, as well as salts derived from relatively non-toxic organic acids including acetic acid, propionic acid, isobutyric acid, oxalic acid, maleic acid, malonic acid, benzoic acid, succinic acid, suberic acid, fumaric acid, mandelic acid, phthalic acid, benzenesulfonic acid, p-tolylsulfonic acid, p-toluenesulfonic acid, citric acid, tartaric acid, methanesulfonic acid, and the like, as well as salts derived from relatively non-toxic organic acids including acetic acid, propionic acid, isobutyric acid, oxalic acid, maleic acid, malonic acid, benzoic acid, succinic acid, suberic acid, fumaric acid, mandelic acid, phthalic acid, benzenesulfonic acid, p-tolylsulfonic acid, p-toluenesulfonic acid, citric acid, tartaric acid, methanesulfonic acid, and the like, Also included are salts of amino acids such as arginate and its analogs, and analogs of organic acids such as glucuronic or galacturonic acid and its analogs. Certain compounds of the present invention possess both basic and acidic functionalities that allow the compounds to be converted into base or acid addition salts. Other examples of salts are disclosed in literature known in the art.

[0031] Non-limiting examples of compounds of Formula I according to the present disclosure are the compounds prepared in the Examples below. The number of each Example corresponds to the compound number. For example, the final compound prepared in Example 15 is Compound 15.

[0032] Among the above compounds, in particular N-(2-(7-chloro-4-oxobenzo[d][1,2,3]triazin-3(4H)-yl)ethyl)-2-(trifluoromethyl)benzamide (Compound 2); N-(2-(6-chloro-4-oxobenzo[d][1,2,3]triazin-3(4H)-yl)ethyl)-2-(trifluoromethyl)benzamide (Compound 1); N-(1-(7-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)-2-methylpropan-2-yl)-2-(trifluoromethyl)benzamide (compound 8); N-(1-(7-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)-2-propan-2-yl)-2-(trifluoromethyl)benzamide (compound 9); N-(2-(7-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)-propyl)-2-(trifluoromethyl)benzamide (compound 10); N-(2-(7-chloro-4-oxobenzo[d][1,2,3]triazin-3(4H)-yl)-2-phenylethyl)-2-(trifluoromethyl)benzamide (compound 11); N-(2-(7-chloro-4-oxobenzo[d][1,2,3]triazin-3(4H)-yl)-1-phenylethyl)-2-(trifluoromethyl)benzamide (compound 12); N-(2-(7-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)-2-methylpropyl)-2-(trifluoromethyl)benzamide (compound 13); N-((1-(7-chloro-4-oxobenzo[d][1,2,3]triazin-3(4H)-yl)cyclopropyl)methyl)-2-(trifluoromethyl)benzamide (compound 14); N-(2-(6-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)-propyl)-2-(trifluoromethyl)benzamide (compound 15); N-(1-(6-chloro-4-oxobenzo[d][1,2,3]triazin-3(4H)-yl)propan-2-yl)-2-(trifluoromethyl)benzamide (compound 16); N-(2-(6-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)-2-methylpropyl)-2-(trifluoromethyl)benzamide (compound 17); N-(2-(4-oxo-6-(trifluoromethyl)benzo[d][1,2,3]triazine-3(4H)-yl)propyl)-2-(trifluoromethyl)benzamide (compound 18); N-(1-(4-oxo-6-(trifluoromethyl)benzo[d][1,2,3]triazin-3(4H)-yl)propan-2-yl)-2-(trifluoromethyl)benzamide (compound 19); N-(2-(7-bromo-4-oxobenzo[d][1,2,3]triazin-3(4H)-yl)ethyl)-2-(trifluoromethyl)benzamide (compound 24); N-(2-(4-oxo-6-(trifluoromethyl)benzo[d][1,2,3]triazin-3(4H)-yl)ethyl)-2-(trifluoromethyl)benzamide (compound 25); N-(2-(4-oxo-7-(trifluoromethyl)benzo[d][1,2,3]triazin-3(4H)-yl)ethyl)-2-(trifluoromethyl)benzamide (Compound 26); or an agronomically acceptable salt thereof, is more preferred for various purposes of the present invention.

[0033] The compounds of the present invention can be produced, for example, according to the following Production Methods 1 and 2, but the present invention is not limited to these production methods.

[0034] <Manufacturing method 1> [ka]

[0035] (In Production Method 1, Y, A, Z, R1, R2, R3, and R4 are as defined in Chemical Formula I above, and L1 represents a leaving group such as a chlorine atom or a hydroxy group.)

[0036] The compound of the present disclosure represented by chemical formula (I) can be produced by reacting a carboxylic acid derivative represented by chemical formula (II) with a ((4-oxobenzo[1,2,3]triazinyl)ethylamine salt derivative represented by chemical formula (III) in an inert solvent in the presence of a base. In this reaction, the reaction temperature is usually in the range of about -20°C to 120°C, and the reaction time is usually in the range of about 1 hour to 48 hours. The ((4-oxobenzo[1,2,3]triazinyl)ethylamine salt derivative represented by chemical formula (III) is usually used in an amount in the range of about 1.0 to 1.5 times by mole relative to the carboxylic acid derivative represented by chemical formula (II).

[0037] Examples of the base include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate; acetates such as sodium acetate and potassium acetate; alkali metal alkoxides such as potassium t-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine, and 1,8-diazabicyclo[5.4.0]undec-7-ene; and nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine. The amount of base is usually in the range of about 1 to 5 moles relative to the carboxylic acid derivative represented by chemical formula (II). Any inert solvent can be used as long as it does not significantly inhibit the reaction, and examples thereof include alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol; linear or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride, and halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; nitriles such as acetonitrile; esters such as ethyl acetate; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, water, and acetic acid. These inert solvents can be used alone or in combination.

[0038] <Manufacturing method 2> [ka]

[0039] (In Production Method 2, A, Z, R1, R2, R3, and R4 are as defined in Chemical Formula I above.)

[0040] An anthranilic acid derivative represented by chemical formula (IV) can be reacted with a compound represented by chemical formula (V) in an inert solvent in the presence of an amide coupling reagent and a base to produce an anthranilamide derivative represented by chemical formula (VI). In this reaction, the reaction temperature is usually in the range of about 20°C to 70°C, and the reaction time is usually in the range of about 12 to 48 hours. The compound represented by chemical formula (V) is usually used in an amount of about 1.0 to 1.5 times the molar amount of the derivative represented by chemical formula (IV). Examples of amide coupling reagents include dicyclohexylcarbodiimide (DCC), diisopropylcarbodiimide (DIC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), carbonyldiimidazole (CDI), (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP), (7-azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyAOP), bromobenzotriazol-1-yloxy, ... Examples of suitable amide coupling reagents include pyrrolidinophosphonium hexafluorophosphate (PyBrOP), O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU), O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (TBTU), O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU), and O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (TATU). The amount of amide coupling reagent used is approximately 1 to 2 times the molar amount of the compound represented by chemical formula (IV). Examples of the base include tertiary amines such as triethylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene, etc. The amount of the base used is in the range of about 2 to 5 moles relative to the compound represented by chemical formula (IV).

[0041] The ((4-oxobenzo[1,2,3]triazinyl)ethylamine derivative represented by the chemical formula (VII) can be produced by reacting the anthranilamide derivative represented by the chemical formula (VI) with sodium nitrite in the presence of an acid in an inert solvent. In this reaction, the reaction temperature is usually in the range of about -10°C to 0°C, and the reaction time is usually in the range of 5 to 24 hours. Sodium nitrite is usually used in a molar amount of 2 to 3 times that of the derivative represented by the chemical formula (VI).

[0042] A ((4-oxobenzo[1,2,3]triazinyl)ethylamine salt derivative represented by chemical formula (III) can be produced by reacting a ((4-oxobenzo[1,2,3]triazinyl)ethylamine derivative represented by chemical formula (VII) in the presence of hydrochloric acid in an inert solvent. In this reaction, the reaction temperature is usually in the range of about 0°C to 30°C, and the reaction time is usually in the range of about 5 to 12 hours. Hydrochloric acid is used as a reagent dissolved in an organic solvent, and is usually used in an amount in the range of about 3 to 5 times the molar amount of the derivative represented by chemical formula (VII). Examples of the hydrochloric acid reagent dissolved in an organic solvent include a 4M dioxane solution, a 2M diethyl ether solution, and a 3M methanol solution.

[0043] After the reaction is complete, the target product can be obtained by separating the target product from the reaction mixture using a conventional method. Generally, the reaction mixture can be purified by precipitating the desired compound in an appropriate solvent, and if necessary, the target product can be obtained by purifying the product using recrystallization, column chromatography, etc.

[0044] The compounds of the present disclosure can be used to combat nematodes, such as root-knot nematodes, cyst nematodes, and root-rot nematodes, to reduce crop yield, inhibit crop growth, and control plant diseases.

[0045] Therefore, the present disclosure provides a nematicidal composition comprising the compound according to the present disclosure or an agronomically acceptable salt thereof as an active ingredient, i.e., an agricultural and horticultural plant pest control agent comprising the compound according to the present disclosure or an agronomically acceptable salt thereof as an active ingredient.

[0046] The present invention also provides a method for controlling nematodes in plants, which comprises treating a target plant or soil with an effective amount of a compound according to the present disclosure or an agronomically acceptable salt thereof.

[0047] The present invention also provides use of the compound according to the present disclosure or an agronomically acceptable salt thereof for the manufacture of a nematicidal formulation, particularly an agent for controlling agricultural and horticultural plant pests.

[0048] The compounds of formula I are particularly useful in controlling nematodes. Thus, in one aspect, the present invention also relates to plant parasitic nematodes (endoparasitic nematodes, semiendoparasitic nematodes and ectoparasitic nematodes), in particular plant parasitic nematodes such as root-knot nematodes, carrot root-knot nematode (Meloidogyne hapla), sweet potato root-knot nematode (Meloidogyne incognita), Javanica root-knot nematode (Meloidogyne javanica), peanut root-knot nematode (Meloidogyne arenaria) and other Meloidogyne species; cyst nematodes, potato cyst nematode (Globodera rostochiensis) and other Globodera species; grain cyst nematode (Heterodera avenae), soybean cyst nematode (Heterodera glycines, sugar beet cyst nematode (Heterodera schachtii), clover cyst nematode (Heterodera trifolii) and other Heterodera spp.; seed gall nematode (Anguina spp.); stem and foliar nematode (Aphelenchoides spp.); sting nematode (Eelonolaimus longicaudatus) and other Belonolaimus spp.; pine nematode (Bursaphelenchus xylophilus) and other Bursaphelenchus spp.; ring nematode (Criconema spp.), Criconemella spp., Criconemoides spp., Mesocriconema spp.) species; stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; awl nematodes, Dolichodorus spp.; spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus spp.; sheath and sheathoid nematodes, Hemicycliophora spp. and Hemicriconemoides spp.; Hirshmanniella spp.; Lance nematodes nematode, Hoploaimus spp.; false rootknot nematode, Nacobbus spp.) species; needle nematode, Longidorus elongatus and other Longidorus species; pin nematode, Pratylenchus species; Lesion nematode, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; burrowing nematode, Radopholus similis and other Radopholus species; Reniform nematode, Rotylenchus robustus, Rotylenchus reniformis and other Rotylenchus species; Scutellonema spp.; Stubby root nematode, Trichodorus primitivus and other Trichodorus species, Paratrichodorus spp.; Stunt nematode, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematode nematode, Tylenchulus spp.; Dagger nematode, Xiphinema spp.; and other plant-parasitic nematode species, such as Subanguina spp., Hypsoperine spp., Macroposthonia spp.The present invention relates to a method for controlling damage to plants and parts thereof caused by Melinius spp., Punctodera spp., and Quinisulcius spp.

[0049] In particular, the compounds of the present invention are further useful for controlling root-knot nematodes (Meloidogyne spp.), cyst nematodes (Heterodera spp., Globodera spp.), root-rot nematodes (Pratylenchus spp.), Rotylenchus spp., and the like.

[0050] The nematicidal composition of the present invention can be formulated into various forms, such as emulsions, suspensions, dusts, granules, tablets, wettable powders, water-soluble powders, liquids, flowable agents, water-dispersible granules, aerosols, pastes, emulsions, and fumigants, by blending with carriers and other adjuvants commonly used in formulations as agricultural chemical adjuvants. In this regard, both solid and liquid carriers can be used as carriers depending on the intended use. Examples of solid carriers include starch; activated carbon; animal and plant powders such as soybean flour, wheat flour, wood flour, fish meal, and milk powder; and inorganic powders such as talc, kaolin, bentonite, calcium carbonate, zeolite, diatomaceous earth, white carbon, clay, alumina, ammonium sulfate, and urea. Examples of liquid carriers include water; alcohols such as isopropyl alcohol and ethylene glycol; ketones such as cyclohexanone and methyl ethyl ketone; ethers such as dioxane and tetrahydrofuran; aliphatic hydrocarbons such as kerosene and light oil; aromatic hydrocarbons such as xylene, trimethylbenzene, tetramethylbenzene, methylnaphthalene, and solvent naphtha; halogenated hydrocarbons such as chlorobenzene; acid amides such as dimethylacetamide; esters such as glycerol esters of fatty acids; nitriles such as acetonitrile; and sulfur-containing compounds such as dimethyl sulfoxide.

[0051] When the extender used is water, organic solvents may also be used as co-solvents.

[0052] Examples of surfactants include metal alkylbenzenesulfonates, metal dinaphthylmethanedisulfonates, alcohol sulfates, alkylarylsulfonates, ligninsulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ethers, and polyoxyethylene sorbitan monoalkylates.

[0053] Other adjuvants that may be used include, for example, adhesives or thickeners such as carboxymethyl cellulose, gum arabic, sodium alginate, guar gum, tragacanth gum, and polyvinyl alcohol; antifoaming agents such as metal soaps; physical property improvers such as fatty acids, alkyl phosphates, silicones, and paraffins; and colorants.

[0054] When actually used, these formulations may be used as is or diluted to a predetermined concentration with a diluent such as water. Various formulations containing the compounds of the present disclosure as active ingredients or their dilutions may be applied by commonly used methods, such as application (e.g., spraying, misting, atomizing, dust application, granule application, water surface application, box application, etc.), soil application (e.g., incorporation, irrigation, etc.), surface application (e.g., painting, smearing, coating, etc.), dipping, poison bait, and fumigation. The amount used may be determined appropriately depending on the formulation, damage, application method, and application location. That is, the compositions of the present disclosure may be applied by conventional methods, such as irrigation, spraying, fogging, dusting, scattering, foaming, sprinkling, etc. The active compound may also be applied by a minimal volume method, or the active compound formulation or the active compound itself may be injected into the soil. Plant seeds may also be treated.

[0055] The nematicidal composition of the present disclosure may generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of the active compound based on the total weight of the composition.

[0056] If necessary, the activity and activity spectrum of the active compounds used according to the invention or of the compositions, concentrates or very general formulations produced therefrom may be increased by adding other antimicrobial active compounds, fungicides, bactericides, herbicides, insecticides or other active compounds in order to broaden the activity spectrum or to obtain specific effects, such as additional protection against insects, etc. These mixtures may have a broader activity spectrum than the compounds according to the invention. [Effects of the Invention]

[0057] The present invention provides compounds that have superior performance compared to the prior art, particularly compounds that have high control effects at low dosages as agricultural and horticultural plant nematode control agents. DETAILED DESCRIPTION OF THE INVENTION

[0058] Hereinafter, the present invention will be described in detail with reference to examples to facilitate understanding of the present invention. However, the examples according to the present invention can be modified into various other forms, and the scope of the present invention should not be construed as being limited to the following examples. The examples of the present invention are provided to more completely explain the present invention to those skilled in the art to which the present invention pertains.

[0059] Example 1 Synthesis of N-(2-(4-oxo-7-(trifluoromethyl)benzo[d][1,2,3]triazin-3(4H)-yl)ethyl)-2-(trifluoromethyl)benzamide (Compound 26)

[0060] [ka]

[0061] 3-(2-aminoethyl)-7-(trifluoromethyl)benzo[d][1,2,3]triazin-4(3H)-one hydrochloride (100 mg, 0.34 mmol) in salt form was dissolved in dichloromethane (1.7 mL), and then 2-(trifluoromethyl)benzoyl chloride (1.5 eq.) and triethylamine (3 eq.) were slowly added. The reaction mixture was stirred at 25°C for 3 hours. The completion of the reaction was confirmed by TLC. After the completion of the reaction, the mixture was acidified with 1N aqueous hydrochloric acid and purified with dichloromethane and water. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Hex:EA=1:1) to yield 114 mg (78%) of the compound of the above formula as a white solid.

[0062] 1 H NMR (300 MHz, Acetone-d6) δ 8.18 (d, J = 8.1 Hz, 1H), 7.93 (s, 1H), 7.91-7.77 (m, 1H), 7.77-7.56 (m, 5H), 4.74-4.60 (m, 2H), 3.97-3.90 (m, 2H).

[0063] <Example 1-1> Synthesis of 2-amino-5-(trifluoromethyl)benzoic acid

[0064] [ka]

[0065] 2-Nitro-4-(trifluoroethyl)benzonitrile (50.0 g, 231.35 mmol) was dissolved in acetic acid (462 ml), and then iron powder (38.8 g, 694.06 mmol) was added in portions while the reaction flask was immersed in an ice bath. After confirming that no heat was being generated from the reaction, the flask was stirred at 40 °C for 24 hours. After the reaction was completed, the remaining excess iron powder was removed using a Celite pad filter. The mixture was then washed with ethyl acetate and concentrated under reduced pressure. The concentrated compound was diluted with ethyl acetate (200 ml) and washed twice with saturated aqueous sodium bicarbonate (2 × 100 ml). The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to yield 42.7 g (99%) of 2-amino-4-(trifluoromethyl)benzonitrile.

[0066] 1 H NMR (300 MHz, CDCl3): δ7.44 (d, J = 8.24 Hz, 1 H ), 6.95 (s, 1H), 6.90 (d, J = 8.24 Hz, 1H), 4.71 (br s, 2H).

[0067] 2-Amino-4-(trifluoromethyl)benzonitrile (42.7 g, 229.40 mmol) was dissolved in concentrated hydrochloric acid (450 ml), concentrated sulfuric acid (20 ml) was slowly added dropwise, and the reaction mixture was stirred at 120° C. for 48 hours. After the reaction was completed, the mixture was extracted with ethyl acetate (3 x 400 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to yield 38.0 g (81%) of 2-amino-4-(trifluoromethyl)benzoic acid.

[0068] 1 H NMR (300MHz, CDCl3) δ7.99 (d, J = 8.4 Hz, 1H), 6.90 (s, 1H), 6.84 (d, J = 8.4 Hz, 1H), 5.94 (br s, 2H).

[0069] <Example 1-2> Synthesis of tert-butyl (2-(2-amino-5-(trifluoromethyl)benzamido)ethyl)carbamate

[0070] [ka]

[0071] 2-Amino-4-(trifluoromethyl)benzoic acid (100 mg, 0.49 mmol) and tert-butyl (2-aminoethyl)carbamate (1 eq.) were reacted in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carboximide hydrochloride (1.2 eq.), hydroxybenzotriazole (1.2 eq.), and diisopropylethylamine (1.6 eq.) in dichloromethane (2.5 mL). The reaction mixture was stirred at 25°C for 3 hours. The completion of the reaction was confirmed by TLC. After completion of the reaction, the mixture was purified with dichloromethane and water. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Hex:EA=1:1) to yield 119 mg (70%) of the compound of the above formula as a white solid.

[0072] 1 H NMR (300 MHz, Acetone-d6) δ 7.88 (s, 1H), 7.70 (d, J = 8.2 Hz, 1H), 7.11-7.08 (m, 1H), 6.81 (dd, J = 8.1, 1.8 Hz, 1H), 6.60 (s, 2H), 6.27 (s, 1H), 3.48 (q, J= 5.7 Hz, 2H), 3.33 (q, J = 5.9 Hz, 2H), 1.42 (s, 9H).

[0073] <Examples 1-3> Synthesis of tert-butyl (2-(4-oxo-6-(trifluoromethyl)benzo[d][1,2,3]triazine-3(4H)-yl)ethyl)carbamate

[0074] [ka]

[0075] Sodium nitrite (2.5 eq.) was dissolved in 0.5 N aqueous hydrochloric acid (3 mL) at 0°C, and then tert-butyl (2-(2-amino-5-chlorobenzamido)ethyl)carbamate (100 mg, 0.32 mmol) dissolved in dimethylformamide (0.2 mL) was slowly added. The reaction mixture was stirred at 0°C for 1 hour, and the completion of the reaction was confirmed by TLC. After the completion of the reaction, the formed solid was washed with water (3 mL) to yield 85 mg (74%) of the compound of the above formula in the form of a white solid.

[0076] 1 H NMR (300 MHz, Acetone-d6) δ 8.57-8.46 (m, 2H), 8.26-8.17 (m, 1H), 6.28 (s, 1H), 4.63-4.54 (m, 2H), 3.69-3.57 (m, 2H), 1.29 (s, 9H).

[0077] <Examples 1-4> Synthesis of 3-(2-aminoethyl)-6-(trifluoromethyl)benzo[d][1,2,3]triazin-4(3H)-one

[0078] [ka]

[0079] tert-Butyl (2-(6-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)ethyl)carbamate (100 mg, 0.31 mmol) was dissolved in 1,4-dioxane (1 mL), and then 4.0 M hydrochloric acid (3 mL) dissolved in 1,4-dioxane was added and stirred at 25°C for 1 hour. The completion of the reaction was confirmed by TLC. After completion of the reaction, the formed solid was washed with diethyl ether (3 mL). 91 mg (99%) of the compound of the above formula was obtained in the form of a white solid.

[0080] 1 H NMR (300 MHz, Methanol-d4) δ 8.61-8.52 (m, 2H), 8.27-8.18 (m, 1H), 4.87-4.77 (m, 2H), 3.60-3.50 (m, 2H).

[0081] The compounds prepared in the same manner as in Example 1 and the NMR data of the compounds are summarized in Table 1 below.

[0082] In this specification, "Me" means a methyl group, "Et" means an ethyl group, "Pr" means a propyl group, "Bu" means a butyl group, "Ph" means a phenyl group, "n-" means normal, "i-" means iso, and "t-" means tertiary.

[0083] [Table 1] TIFF2025525642000014.tif232170TIFF2025525642000015.tif239170TIFF2025525642000016.tif239170TIFF2025525642000017.tif125170

[0084] <Test Example 1> Test of nematicidal effect against root-knot nematodes (in vitro) Tomato (cv. Seogwang, Monsanto Korea) roots were infected with root-knot nematodes (Meloidogyne incognita) and grown in a greenhouse (25±5°C) for approximately six weeks. Roots bearing egg sacs were then harvested, washed thoroughly under running water, and cut into pieces less than 1 cm in size. The cuttings were placed in a flask, 0.5% sodium hypochlorite solution (NaOCl) was added, and the mixture was shaken vigorously for three minutes to remove the egg sacs. The root residue was filtered through a 65 μm sieve. The permeate was then passed through a 25 μm sieve again to separate the nematode eggs remaining on the sieve. The harvested M. incognita eggs were hatched into larvae for use in experiments using a triangular funnel at 25°C. Second-instar nematode larvae were collected in a beaker, and the nematode density was examined under a microscope. The concentration was then adjusted to 300 nematodes / ml by dilution.

[0085] The experimental drugs were dissolved in dimethyl sulfoxide (DMSO) and prepared at a concentration 100 times the experimental concentration (50 ppm). 1 μl of the drug was placed per well in a 96-well plate, and 99 μl of the prepared nematode suspension was added to each well and shaken vigorously. Control drug and untreated controls were also tested. The control drug was treated with 4 μg / ml of cadusafos, while the untreated controls were treated with 1 μl of DMSO alone. Each experiment was performed three times. The drug-treated nematode plates were incubated at 25°C for 48 hours, after which the number of dead nematodes was counted under a microscope and the nematode mortality rate was calculated. Since all nematodes in the untreated group were alive, the nematode mortality rate (%) was equivalent to the nematocidal activity.

[0086] The nematicidal effects of the prepared compounds are summarized in the following Table 2. In the following Table 2, the concentration of the test substance was 50 ppm.

[0087] [Table 2] TIFF2025525642000019.tif242170TIFF2025525642000020.tif239170TIFF2025525642000021.tif234170TIFF2025525642000022.tif50170

[0088] <Test Example 2> Test of the control effect of tomato root-knot nematodes (in vivo) 1) Plant preparation Disposable pots (90 ml) were filled to approximately 70% with horticultural soil (Punong Co.), and tomato (variety: Seogwang, Monsanto Korea) seeds were sown at 2-3 seeds per pot. The seeds were then covered with a 1:1 mixture of horticultural soil and vermiculite and cultivated in a greenhouse (25 ± 5°C). After approximately 10 days, the seeds were thinned out to leave one tomato plant per pot and then cultivated. Tomato seedlings cultivated approximately 3 weeks after sowing were used in the experiment.

[0089] 2) Preparation of inoculum Tomato (cv. Seogwang, Monsanto Korea) roots were infected with root-knot nematodes (Meloidogyne incognita) and cultivated in a greenhouse (25±5°C) for approximately six weeks. Roots with egg sacs were harvested, washed thoroughly under running water, cut into pieces less than 1 cm in size, and placed in a flask. A 0.5% sodium hypochlorite solution (NaOCl) was added and vigorously shaken for three minutes to remove the egg sacs. The mixture was passed through a 65 μm sieve to filter the root residue, and the permeate was passed through a 25 μm sieve again to separate the nematode eggs remaining on the sieve. The separated nematode eggs were added to sterilized distilled water to prepare a nematode egg suspension. The egg density was then examined under a microscope and diluted to 500 eggs per ml.

[0090] 3) Preparation of drug solution The compound was dissolved in acetone at a concentration 100 times higher than the target concentration, and then added to 99 ml of Tween 20 solution (250 μg / ml) to give a final acetone concentration of 1% to prepare a drug solution.

[0091] 4) Nematode inoculation and drug treatment For in vivo experiments with root-knot nematodes (Meloidogyne incognita), 200 g of sterilized sandy soil was placed in the bottom of a 9.5 cm diameter pot, and a cultivated tomato plant was placed on top of the soil. 100 g of horticultural soil (Punong) was then added. 10 ml of the prepared nematode egg suspension was then inoculated around the tomato plant using a micropipette, resulting in 5,000 nematode eggs per pot.

[0092] One hour after inoculation, 20 ml of the prepared pesticide solution was drenched into the soil around the tomatoes per pot. For the control group, a solution containing 1% acetone and 250 μg / ml Tween 20 without the pesticide was drenched in the same manner.

[0093] 5) Disease investigation and calculation of control value All experiments were repeated five times per treatment. The pots inoculated with nematodes and treated with pesticides were cultivated in a greenhouse (25±5°C) for 6 weeks, and then examined for disease using the following method.

[0094] The disease survey was conducted by assigning a gall index from 0 to 10 according to the degree of gall formation on the tomato roots: 0: healthy roots, 1: galls on 1-10% of the roots, 2: galls on 11-20% of the roots, 3: galls on 21-30% of the roots, 4: galls on 31-40% of the roots, 5: galls on 41-50% of the roots, 6: galls on 51-60% of the roots, 7: galls on 61-70% of the roots, 8: galls on 71-80% of the roots, 9: galls on 81-90% of the roots, and 10: galls on 91-100% of the roots.

[0095] The control value was calculated using the following formula (Formula 1). Control value (%) = (1 - gall index of treated area / gall index of untreated area) x 100 Judgment criteria 0: Control value 9% or less 1: Control value 10-29% 2: Control value 30-49% 3: Control value 50-69% 4: Control value 70-89% 5: Control value 90-100% As a result of the test, the compounds of the present invention exhibited excellent control effects at an active ingredient concentration of 100 ppm, and in particular, Compounds Nos. 6, 7, 9, 10, 13, 14, 24 and 26 exhibited high activity meeting the evaluation standard of 5.

[0096] <Test Example 3> Compound 26 according to an embodiment of the present invention was compared with the following two compounds as control compounds for comparison. A comparative test evaluation of root-knot nematode control was carried out in the same manner as in Test Examples 1 and 2 described above. The results are shown in Table 3 below.

[0097] Comparative compound A: N-(2-(4-oxobenzo[d][1,2,3]triazin-3(4H)-yl)ethyl)benzo[d][1,2,3]thiadiazole-7-carboxamide (compound No. 1 of chemical formula (IV) in Patent Document 1)

[0098] Comparative compound B: 4-(tert-butyl)-N-(3-(5-chloro-4-oxobenzo[d][1,2,3]triazin-3(4H)-yl)propyl)benzamide (compound No. 38 of chemical formula (IV) in Patent Document 1)

[0099] [Table 3]

[0100] As shown in Table 3, compound 26 of the present invention exhibited a high nematicidal effect, whereas comparative compounds A and B, which are structurally similar compounds, had no direct nematicidal effect (in vitro) against root-knot nematode larvae (J2, second instar worms) under the same conditions, nor did they have any control effect against tomato root-knot nematodes (inhibitory effect on root-knot formation, in vivo).

[0101] <Test Example 4> Test of nematicidal effect against soybean cyst nematodes (in vitro) Soybean (variety: Taekwang) roots were inoculated with eggs and cultivated in a greenhouse (25±5°C) for approximately 8 weeks. The roots and soil containing cysts were then harvested. The cyst nematode-infected plant roots and soil were placed on 20-mesh and 60-mesh sieves and separated under running water. The 60-mesh sieves were then collected. The 60-mesh sieves were placed in 45% sugar water for 30 minutes, after which the soil and cyst mixture were collected. The water from the collected mixture was removed, and the cysts were isolated using a stereomicroscope. The isolated soybean cyst nematode cysts were immersed in soybean exudate and placed in an incubator (26±1°C) to allow the larvae to hatch. Second-instar cyst nematode larvae were collected in a beaker, examined for nematode density under a microscope, and diluted to 50 nematodes / ml.

[0102] The experimental drugs were dissolved in dimethyl sulfoxide (DMSO). They were prepared to be 100 times more concentrated than the experimental concentration (50 ppm). 1 μl of the drug was placed per well in a 96-well plate, and 99 μl of the prepared nematode suspension was added to each well and shaken well. Control drug and untreated samples were also tested. The control drug was treated with 1 μl of 5,000 ppm fluopyram, while the untreated sample was treated with 1 μl of DMSO alone without any drug. The experiment was performed three times per treatment, and the drug-treated nematode plates were cultured at 26°C for 72 hours, after which the number of dead nematodes was counted under a microscope and the corrected mortality rate was calculated using the following method (Equation 2). Corrected mortality rate (%) = (survival rate in untreated area compared to initial density - survival rate in treated area compared to initial density) / survival rate in untreated area compared to initial density × 100

[0103] [Table 4]

[0104] As shown in Table 4, compound 26, one embodiment of the present invention, also exhibited excellent effects against soybean cyst nematodes.

[0105] <Test Example 5> Test of nematicidal effect against sugar beet cyst nematodes (in vitro) Sugar beet cyst nematodes (Heterodera schachtii) were collected from infected soil in a cabbage field in Jeongseon County, Gangwon Province, South Korea. Plant roots and soil infected with cyst nematodes were placed on 20-mesh and 60-mesh sieves and separated under running water. The 60-mesh sieves were then collected. The 60-mesh sieves were then placed in 45% sugar water for 30 minutes, after which the soil and cyst mixture was collected. The water from the mixture was removed, and the cysts were isolated using a stereomicroscope. The isolated sugar beet cyst nematode cysts were immersed in cabbage exudate and placed in an incubator (26±1°C) to allow larvae to hatch. Second-instar cyst nematode larvae were collected in a beaker, examined under a microscope, and diluted to a concentration of 50 nematodes / ml.

[0106] The experimental drugs were dissolved in dimethyl sulfoxide (DMSO). They were prepared to be 100 times more concentrated than the experimental concentration (50 ppm). 1 μl of the drug was placed per well in a 96-well plate, and 99 μl of the prepared nematode suspension was added to each well and shaken well. Control drug and untreated samples were also tested. The control drug was treated with 1 μl of 5,000 ppm fluopyram, while the untreated sample was treated with 1 μl of DMSO alone without any drug. The experiment was performed three times per treatment, and the drug-treated nematode plates were cultured at 26°C for 12 days. The number of dead nematodes was counted under a microscope, and the corrected mortality rate was calculated using the following method (Equation 2). Corrected mortality rate (%) = (survival rate in untreated area compared to initial density - survival rate in treated area compared to initial density) / survival rate in untreated area compared to initial density × 100

[0107] [Table 5]

[0108] As shown in Table 5, compounds 6 and 26, which are one embodiment of the present invention, also exhibited excellent effects against sugar beet cyst nematodes.

Claims

1. A compound represented by the following chemical formula I or an agronomically acceptable salt thereof: [Chemical formula I] 【Chemical 1】 In Formula I, Y is, 【Chemistry 2】 where W is CH or N, and Q １ is CF ３ or halogen, and Q ２ is hydrogen, halogen, methyl or CF ３ and R １ , R ２ , R ３ and R ４ are each independently hydrogen, (C １ -C ６ ) alkyl, (C １ -C ３ ) haloalkyl or phenyl, or R １ and R ２ or R ３ and R ４ are connected to each other (C ３ -C ６ ) forming a cycloalkyl, X is O or S; A is a benzene or pyridine fused to the triazine ring on the right, Z is hydrogen, halogen, cyano, —CH═N—O—R′, SR′, S(O) ２ R', NR'R", (C １ -C ６ ) alkyl, (C １ -C ３ ) haloalkyl, (C １ -C ６ ) alkoxy, (C １ -C ３ ) haloalkoxy, substituted or unsubstituted amine, substituted or unsubstituted (C ３ -C ６ ) cycloalkyl, substituted or unsubstituted hetero(C ３ -C ６ ) cycloalkyl, substituted or unsubstituted phenyl, where the substitutions are hydrogen, —OH, halogen, (C １ -C ６ ) alkyl, (C １ -C ３ ) haloalkyl, (C １ -C ６ ) alkoxy, and (C １ -C ３ ) haloalkoxy; R′ and R″ are independently hydrogen, (C １ -C ６ ) alkyl, or (C １ -C ３ ) haloalkyl.

2. Y is, 【Chemistry 3】 where Q ２ is hydrogen, halogen, methyl or CF ３ and R １ , R ２ , R ３ and R ４ are each independently hydrogen, (C １ -C ６ ) alkyl, (C １ -C ３ ) haloalkyl or phenyl, or R １ and R ２ or R ３ and R ４ are connected to each other (C ３ -C ６ ) forming a cycloalkyl, X is O, A is a benzene fused to a triazine ring on the right, Z is hydrogen, halogen, cyano, —CH═N—O—R′, SR′, S(O) ２ R', NR'R", (C １ -C ６ ) alkyl, (C １ -C ３ ) haloalkyl, (C １ -C ６ ) alkoxy, (C １ -C ３ ) haloalkoxy, substituted or unsubstituted amine, substituted or unsubstituted (C ３ -C ６ ) cycloalkyl, substituted or unsubstituted hetero(C ３ -C ６ ) cycloalkyl, substituted or unsubstituted phenyl, where the substitutions are hydrogen, —OH, halogen, (C １ -C ６ ) alkyl, (C １ -C ３ ) haloalkyl, (C １ -C ６ ) alkoxy, and (C １ -C ３ ) haloalkoxy; R′ and R″ are independently hydrogen, (C １ -C ６ ) alkyl, or (C １ -C ３ ) haloalkyl; 2. The compound of claim 1 or an agronomically acceptable salt thereof.

3. Y is, 【Chemistry 4】 and R １ , R ２ , R ３ and R ４ are each independently hydrogen, (C １ -C ３ ) alkyl or phenyl, or R １ and R ２ or R ３ and R ４ are connected to each other (C ３ -C ６ ) forming a cycloalkyl, X is O, A is a benzene fused to a triazine ring on the right, Z is a halogen, —CH═N—O—R′, (C １ -C ３ ) haloalkyl, (C １ -C ６ ) alkoxy, (C １ -C ３ ) haloalkoxy, substituted or unsubstituted amine, substituted or unsubstituted (C ３ -C ６ ) cycloalkyl, substituted or unsubstituted hetero(C ３ -C ６ ) cycloalkyl, substituted or unsubstituted phenyl, where the substitutions are hydrogen, —OH, halogen, (C １ -C ６ ) alkyl, (C １ -C ３ ) haloalkyl, (C １ -C ６ ) alkoxy, and (C １ -C ３ ) haloalkoxy; R' is hydrogen, (C １ -C ６ ) alkyl, or (C １ -C ３ ) haloalkyl; 3. The compound of claim 2 or an agronomically acceptable salt thereof.

4. Y is, 【Chemistry 5】 and R １ , R ２ , R ３ and R ４ are each independently hydrogen, (C １ -C ３ ) alkyl or phenyl, or R １ and R ２ or R ３ and R ４ are connected to each other (C ３ -C ６ ) forming a cycloalkyl, X is O, A is a benzene fused to a triazine ring on the right, Z is a halogen, (C １ -C ３ ) haloalkyl, or (C １ -C ６ ) is alkoxy; 4. The compound of claim 3 or an agronomically acceptable salt thereof.

5. wherein said formula I is N-(2-(7-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)ethyl)-2-(trifluoromethyl)benzamide (Compound 2); N-(2-(6-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)ethyl)-2-(trifluoromethyl)benzamide (Compound 1); N-(1-(7-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)-2-methylpropan-2-yl)-2-(trifluoromethyl)benzamide (compound 8); N-(1-(7-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)-2-propan-2-yl)-2-(trifluoromethyl)benzamide (compound 9); N-(2-(7-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)-propyl)-2-(trifluoromethyl)benzamide (compound 10); N-(2-(7-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)-2-phenylethyl)-2-(trifluoromethyl)benzamide (compound 11); N-(2-(7-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)-1-phenylethyl)-2-(trifluoromethyl)benzamide (compound 12); N-(2-(7-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)-2-methylpropyl)-2-(trifluoromethyl)benzamide (compound 13); N-((1-(7-chloro-4-oxobenzo[d][1,2,3]triazin-3(4H)-yl)cyclopropyl)methyl)-2-(trifluoromethyl)benzamide (compound 14); N-(2-(6-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)-propyl)-2-(trifluoromethyl)benzamide (compound 15); N-(1-(6-chloro-4-oxobenzo[d][1,2,3]triazin-3(4H)-yl)propan-2-yl)-2-(trifluoromethyl)benzamide (compound 16); N-(2-(6-chloro-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)-2-methylpropyl)-2-(trifluoromethyl)benzamide (compound 17); N-(2-(4-oxo-6-(trifluoromethyl)benzo[d][1,2,3]triazine-3(4H)-yl)propyl)-2-(trifluoromethyl)benzamide (compound 18); N-(1-(4-oxo-6-(trifluoromethyl)benzo[d][1,2,3]triazin-3(4H)-yl)propan-2-yl)-2-(trifluoromethyl)benzamide (compound 19); N-(2-(7-bromo-4-oxobenzo[d][1,2,3]triazine-3(4H)-yl)ethyl)-2-(trifluoromethyl)benzamide (compound 24); N-(2-(4-oxo-6-(trifluoromethyl)benzo[d][1,2,3]triazin-3(4H)-yl)ethyl)-2-(trifluoromethyl)benzamide (compound 25); or N-(2-(4-oxo-7-(trifluoromethyl)benzo[d][1,2,3]triazin-3(4H)-yl)ethyl)-2-(trifluoromethyl)benzamide (compound 26), 10. The compound of claim 1 or an agronomically acceptable salt thereof.

6. A nematicidal composition comprising the compound according to any one of claims 1 to 5 or an agrochemically acceptable salt thereof as an active ingredient.

7. 7. The nematicidal composition of claim 6, wherein the nematode is a root-knot nematode, a cyst nematode, or a root-rot nematode.

8. 6. A method for controlling nematodes in plants, which comprises applying an effective amount of the compound according to any one of claims 1 to 5 or an agrochemically acceptable salt thereof to a target plant or soil.

9. The method for controlling nematodes according to claim 8, wherein the nematode is a root-knot nematode, a cyst nematode, or a root-rot nematode.

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