TW202000657A - Substituted pyridine compound or a salt thereof - Google Patents

Abstract

The present invention provides a substituted pyridine compound represented by the formula (I) or a salt thereof, a pest control agent containing a substituted pyridine compound represented by the formula (I') or a salt thereof as an active ingredient, an agricultural and horticultural insecticide, miticide, nematicide, or soil pesticide containing the substituted pyridine compound represented by the formula (I') or a salt thereof as an active ingredient, and a method for controlling a pest by applying the substituted pyridine compound represented by the formula (I') or a salt thereof. (in the formulae (I) and (I'), for each substituent, see Description).

Description

Substituted pyridine compounds or their salts

The present invention relates to a novel substituted pyridine compound or its salt. In addition, the present invention relates to pest control agents, agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides containing substituted pyridine compounds or their salts as active ingredients. Furthermore, the present invention relates to a method for controlling harmful organisms by applying an effective amount of a substituted pyridine compound or a salt thereof.

Patent Document 1 describes an amide compound widely used in medical applications, but only the specific description of those in which R ⁴ in the formula (I) described below is a hydrogen atom. In addition, Patent Document 2 describes an amide compound widely used in medical applications, but only the specific description of the formula (I) described later in which R ⁴ is piperidine.

In addition, the compounds represented by the following formulas (A) to (C) are commercially known compounds, but the biological properties and specific uses of these compounds are not yet known.

[先前技術文獻] [專利文獻]【Chemistry 1】

[Prior Technical Literature] [Patent Literature]

[Patent Document 1] Japanese Patent Laid-Open No. 2003-73357 [Patent Literature 2] International Publication No. 2008/106692

[Problems to be solved by the invention]

Over the years, a variety of pest control agents have been used by humans, but many control agents have various problems such as insufficient effectiveness, resistance to pests, etc., resulting in restrictions on their use. Therefore, it is desired to develop novel pest control agents with few such disadvantages. The object of the present invention is to provide a compound or salt thereof with high activity against harmful organisms; to provide a pest control agent containing the compound or salt as an effective ingredient, such as agricultural and horticultural insecticides, acaricides, nematicides Or to kill soil insecticides; provide methods of applying the compound or its salts to control pests. [Means to solve the problem]

In order to develop more excellent pest control agents, the inventors of the present case conducted various studies on substituted pyridine compounds. As a result, it was found that a novel substituted pyridine compound or its salt has a high control effect on harmful organisms at a low dose, and this is the completion of the present invention.

That is, the present invention relates to a substituted pyridine compound or its salt, which is represented by formula (I);

【Chemical 2】

In formula (I), A is a substituent represented by formula (A-1) or a substituent represented by formula (A-2); R ³ is a hydrogen atom, an alkyl group, an alkylcarbonyl group or an alkoxycarbonyl group; R ⁴ Nitro, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, (alkylthio)carbonyl or carboxy;

【Chemical 3】

In formula (A-1) or formula (A-2), R ¹ is a hydrogen atom, alkyl group, haloalkyl group, alkoxy group, haloalkoxy group, alkylcarbonyl group, cycloalkyl group, cycloalkoxy group, Alkylthio, alkylsulfinyl, alkylsulfonyl or haloalkylthio; R ² is alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkyl Sulfonyl, alkylsulfonyl or dialkylamine; m is an integer from 0 to 2; when m is 2, R ² may be the same or different.

Furthermore, the present invention relates to a pest control agent (for example, pesticides for agricultural and horticultural use, acaricides, nematicides or soil insecticides) containing a substituted pyridine compound represented by formula (I') or a salt thereof as effective Ingredients, and a method for controlling harmful organisms, is to apply an effective amount of a substituted pyridine compound represented by formula (I') or a salt thereof to control harmful organisms;

【Chemical 4】

In formula (I'), A is a substituent represented by formula (A-1) or a substituent represented by formula (A-2); R ³ is a hydrogen atom, an alkyl group, an alkylcarbonyl group or an alkoxycarbonyl group; R ^{4'is nitro} , halogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, (alkylthio)carbonyl or carboxy;

【Chemical 5】

In formula (A-1) or formula (A-2), R ¹ is a hydrogen atom, alkyl group, haloalkyl group, alkoxy group, haloalkoxy group, alkylcarbonyl group, cycloalkyl group, cycloalkoxy group, Alkylthio, alkylsulfinyl, alkylsulfonyl or haloalkylthio; R ² is alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkyl Sulfonyl, alkylsulfonyl or dialkylamine; m is an integer from 0 to 2; when m is 2, R ² may be the same or different; ^however , ^when R ^{4'is bromine} , R ¹ Not a hydrogen atom. [Effect of invention]

According to the present invention, a compound or a salt thereof having high activity against harmful organisms can be provided, and a pest control agent containing the compound or its salt as an effective ingredient can be provided, such as agricultural and horticultural insecticides, acaricides, and nematicides Or to kill soil insecticides, and can provide methods of applying the compound or its salts to control harmful organisms.

Hereinafter, the present invention will be described in detail, but these are examples of ideal implementations, and the present invention is not limited to these contents. In addition, in this specification, "C _n "(n is a natural number) is synonymous with "carbon number n" (n is a natural number). When the concentration is described as "ppm", it means "weight ppm".

The present invention relates to substituted pyridine compounds represented by formula (I) or salts thereof. In addition, the present invention relates to a pest control agent containing a substituted pyridine compound represented by formula (I') or a salt thereof as an active ingredient (for example, agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides) , And on the application of effective amounts of the compound or its salts to control pests. In addition, the "compound of formula X" referred to below means "the compound represented by formula X".

【Chemical 6】

In formula (I) and formula (I'), each substituent is the same as described above.

The haloalkyl group in the aforementioned formula (I) or formula (I') means an alkyl group in which at least one hydrogen atom contained in the alkyl group is substituted with a halogen atom. The same applies to haloalkoxy or haloalkylthio, which means alkoxy or alkylthio in which at least one hydrogen atom contained in each group is replaced with a halogen atom, respectively. In these haloalkyl groups, haloalkoxy groups, or haloalkylthio groups, a halogen atom in which a hydrogen atom is substituted is called "halogen as a substituent".

The halogen atom as a substituent in the aforementioned formula (I) or formula (I') or the halogen atom in the specification of the present case may include each atom of fluorine, chlorine, bromine or iodine. The number of halogen atoms as a substituent may be 1 or 2 or more. When it is 2 or more, each halogen atom may be the same or different. In addition, the substitution position of the halogen atom may be any position.

Examples of the alkyl group or alkyl moiety in the aforementioned formula (I) or formula (I′) include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and second butyl , A tertiary butyl, n-pentyl, isopentyl, neopentyl, n-hexyl or neohexyl linear or branched chain C ₁ -C ₆ group.

Examples of the alkenyl group or alkenyl moiety in the aforementioned formula (I) or formula (I′) include, for example, 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 -Straight or branched C of pentenyl, 2-pentenyl, 2-methyl-2-butenyl, 1-hexenyl or 2,3-dimethyl-2-butenyl _2- C ₆ basis.

Examples of the alkynyl or alkynyl moiety in the aforementioned formula (I) or formula (I′) include, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl , 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-hexynyl, 2 -A linear or branched C ₂ -C ₆ group of hexynyl, 3-hexynyl, 4-hexynyl, or 5-hexynyl.

Examples of the cycloalkyl or cycloalkyl moiety in the aforementioned formula (I) or formula (I′) include C ₃ -C ₆ groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

The salt of the compound of the aforementioned formula (I) or formula (I′) may be any substance as long as it is permissible in the technical field, including all salts, for example, dimethyl ammonium salt, triethyl Ammonium salts of basic ammonium salts; inorganic salts such as hydrochloride, perchlorate, sulfate, nitrate; such as acetate, trifluoroacetate, oxalate, p-toluenesulfonate, methanesulfonate Organic acid salts.

The compound of the aforementioned formula (I) or a salt thereof, and the compound of the aforementioned formula (I′) or a salt thereof may exist as isomers such as optical isomers, and the present invention includes each isomer and a mixture of isomers Both. In the specification of this case, unless otherwise specified, the isomers are described as a mixture. In addition, the present invention also includes various isomers other than the aforementioned within the scope of technical common knowledge in the technical field. Also, depending on the type of isomer, it may sometimes have a chemical structure different from the compound of the aforementioned formula (I) or formula (I′), but those skilled in the art can fully recognize the relationship between these isomers Therefore, it obviously belongs to the scope of the present invention.

The compound of the aforementioned formula (I) or formula (I′) or a salt thereof (hereinafter also referred to as the compound of the present invention) can be produced according to the following production method, and/or a general salt production method, but is not limited to this And other methods. In addition, the following production methods and intermediate production methods are described for the production of compounds of formula (I), but compounds of formula (I') can be produced according to these production methods using compounds having R ^4′ instead of R ⁴ Compound.

Production method [1] The aforementioned compound of formula (I) can be produced by reacting the compound of formula (II) with the compound of formula (III) in the presence of a dehydrating condensing agent or a base. In addition, commercially available products can be used for the compound of the formula (II) or the compound of the formula (III), and can also be produced by a known method.

【Chemical 7】

In the formula [1], R ³ , R ⁴ and A are the same as described above.

The dehydrating condensation agent is not particularly limited, and examples thereof include 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1,3-dicyclohexylcarbodiimide, O -(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethylurea hexafluorophosphate, etc.

啉、二異丙基乙基胺等三級胺類、1,8-二氮雜雙環[5.4.0]-7-十一烯、吡啶、4-(二甲基胺基)吡啶、2,6-二甲基吡啶等。The base is not particularly limited, for example, triethylamine, 4-methyl

Tertiary amines such as porphyrin and diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 4-(dimethylamino)pyridine, 2, 6-lutidine and so on.

The reaction can be carried out in the presence of a solvent as necessary. The solvent is not particularly limited, for example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, dimethoxyethane, etc.; dichloromethane, dichloroethane , Chloroform and other aliphatic halogenated hydrocarbons; benzene, toluene, xylene, chlorobenzene and other aromatic hydrocarbons; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl Aprotic polar solvents such as -2-pyrrolidone, dimethyl sulfoxide, cyclobutane; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate and ethyl propionate; pentane, hexane, heptane, Aliphatic hydrocarbons such as octane, cyclohexane, etc.; ketones such as acetone, methyl ethyl ketone; water, etc., and one kind may be selected as appropriate, or two or more kinds may be selected and mixed for use.

As far as the reaction temperature is concerned, it can usually be carried out within a range of about 0°C to a temperature at which the reaction system is heated to reflux. In terms of reaction time, it can usually be carried out in a few minutes to 24 hours.

Production method [2] The aforementioned compound of formula (I) can be produced by reacting the compound of formula (II-a) and the compound of formula (III) in the presence of a base.

【Chemical 8】

In the formula [2], R ³ , R ⁴ and A are the same as described above; X is a halogen atom.

The base may be an organic base or an inorganic base. The organic base is not particularly limited, and examples thereof include amine bases such as triethylamine and diisopropylethylamine. The inorganic base is not particularly limited, and examples thereof include alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate.

The reaction can be carried out in the presence of a solvent as necessary. The solvent is not particularly limited, and the same as the production method [1] can be cited.

As far as the reaction temperature is concerned, it can usually be carried out within a range of about 0°C to a temperature at which the reaction system is heated to reflux. In terms of reaction time, it can usually be carried out in a few minutes to 24 hours.

Intermediate production method [1] The compound of the formula (II-a) can be a commercially available product, and it can also be produced by reacting the compound of the formula (II) with a halogenating agent.

[Chem 9]

In the formula of the above intermediate production method [1], A and X are the same as described above.

The halogenating agent is not particularly limited, and examples thereof include thionyl chloride, oxalyl chloride, phospha chloride, sulfa chloride, phosphorus trichloride, and phosphorus pentachloride.

The reaction can be carried out in the presence of a solvent as necessary. The solvent is not particularly limited, for example, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, dimethoxyethane, etc.; dichloromethane, dichloroethane , Chloroform and other aliphatic halogenated hydrocarbons; benzene, toluene, xylene, chlorobenzene and other aromatic hydrocarbons; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl Aprotic polar solvents such as -2-pyrrolidone, dimethyl sulfoxide, cyclobutane; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate and ethyl propionate; pentane, hexane, heptane, Aliphatic hydrocarbons such as octane and cyclohexane; ketones such as acetone and methyl ethyl ketone, etc., can be appropriately selected and used, or two or more kinds can be appropriately selected and mixed for use.

As far as the reaction temperature is concerned, it can usually be carried out within a range of about 0°C to a temperature at which the reaction system is heated to reflux. In terms of reaction time, it can usually be carried out in a few minutes to 24 hours.

Intermediate production method [2] The aforementioned compound of formula (III) can be produced by reacting the compound of formula (III-a) with the compound of formula (IV). The compound of the formula (III-a) or the compound of the formula (IV) can be a commercially available product, and can also be produced by a known method.

【Chemical 10】

In the formula of the above intermediate production method [2], R ³ , R ⁴ and X are the same as described above.

啉、二異丙基乙基胺等三級胺類；1,8-二氮雜雙環[5.4.0]-7-十一烯、吡啶、4-(二甲基胺基)吡啶、2,6-二甲基吡啶等。This reaction can be carried out in the presence of a base as necessary. Examples of the base include: alkali metal hydrides such as sodium hydride; alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide; triethyl Amine, 4-methyl

Tertiary amines such as porphyrin and diisopropylethylamine; 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 4-(dimethylamino)pyridine, 2, 6-lutidine and so on.

The reaction can be carried out in the presence of a solvent as necessary. The solvent is not particularly limited, and the same as the production method [1] can be cited.

As far as the reaction temperature is concerned, it can usually be carried out within a range of about 0°C to a temperature at which the reaction system is heated to reflux. In terms of reaction time, it can usually be carried out in a few minutes to 24 hours.

The ideal form of the pest control agent containing the compound of the present invention as an active ingredient will be described below. A pest control agent containing the compound of the present invention as an active ingredient, for example, as a control agent for pests, mites, nematodes or soil pests that is a problem in the agricultural and horticultural fields, that is, as an insecticide, acaricide, and killing agent for agricultural and horticultural purposes Nematodes or soil insecticides are useful. Moreover, it is useful as a control agent for animal parasites, that is, as an animal parasitic agent system.

The compounds of the present invention are effective against the following control systems: Aphidoidea such as Myzus persicae and Aphis gossypii; Plutella xylostella, Plutella xylostella, Mamestra brassicae, and twill Spodoptera litura, Cydia pomonella, Bollworm, Tobacco budworm, Lymantria dispar, Cnaphalocrocis medinalis, Leaf moth (Adoxophyes honmai), Delphacidae, Cicadellidae, and scale insects such as Leptinotarsa decemlineata, Aulacophora femoralis, Boll weevil, Nilaparvata lugens, etc. Coccoidea, Pentatomidae, Aleyrodidae, Thysanoptera, Acrididae, Anthomyiidae, Chaferidae, such as Bemisia tabaci (Scarabaeidae), Agrotis ipsilon, Agrotis segetum, formicidae and other agricultural pests; gastropods such as slugs and snails; such as Ornithonyssus bacoti, Blattodea ), houseflies, Culex pipiens pallens and other health pests; such as wheat moths (Sitotroga cerealella), mung bean elephants (Callosobruchus chinensis), tribolium castaneum, and Tenebrionidae Stored grain pests such as clothing moths (Tinea pellionella), bonito beetles (Attagenus japonicus), termites and other clothing, house pests and other pests; such as two-spotted spider mite (Tetranychus urticae), red spider mite (Tetranychus cinnabarinus ), Tetranychus kanzawai Kishida, Citrus spider mite (Panonychus citri), European plant mites (Panonychus ulmi), polyphagotarsonemus latus, Aculops pelekassi, bulb mite and other plant parasitic mites; such as Tyrophagus putrescentiae, American dust mite (Dermatophagoides farinae), house mites (Chelacaropsis Moorei) and other mites such as house mites; such as root-knot nematode, cyst nematode, root lesion nematode ), rice white-tip nematode, strawberry bud nematode, pine wood nematode and other plant parasitic nematodes; such as wood louse, tide Pests (Porcellio scaber) and other isopods and other soil pests. The agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides containing the compound of the present invention as an active ingredient are particularly effective for the control of plant parasitic mites, agricultural pests, plant parasitic nematodes and the like. Among them, it exhibits more excellent effects in the control of plant parasitic mites and agricultural pests, so it is very useful as an insecticide or acaricide system. In addition, agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides containing the compound of the present invention as an active ingredient, for the control of organic phosphorus agents, carbamate agents, and synthetic pyrethroids (Pyrethroid) Agents, neonicotinoid agents, and other resistant pests that are resistant are also effective. Furthermore, the compound of the present invention has excellent osmotic migration, so by treating the soil with an agricultural, horticultural insecticide, acaricide, nematicide, or soil insecticide containing the compound of the present invention as an active ingredient, Prevent and control soil harmful insects, mites, nematodes, gastropods and other foot species, as well as pests in stems and leaves.

Another ideal aspect of the pest control agent containing the compound of the present invention as an active ingredient may include agricultural and horticultural comprehensive control of the aforementioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests, etc. Use insecticides, acaricides, nematicides or soil insecticides.

The pest control agent containing the compound of the present invention as an active ingredient is usually prepared by mixing the compound with various adjuvants into powder, granule, granule hydrating agent, hydrating agent, aqueous suspension agent, oily suspension agent, granular water solvent, Aqueous solvents, emulsions, liquids, pastes, aerosols, micro-dispersants, etc. are used in various forms, but as long as they meet the purposes of the present invention, they can be prepared in any form commonly used in this field. Examples of auxiliary agents used in the preparation include diatomite, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, thenardite, zeolite, starch and other solid carriers ; Water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N,N-dimethyl methyl Acetamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, alcohol and other solvents; such as fatty acid salt, benzoate, alkylsulfosuccinate, dialkylsulfosuccinate Acid salt, polycarboxylate, alkyl sulfate, alkyl sulfate, alkyl aryl sulfate, alkyl diglycol ether sulfate, alcohol sulfate, alkyl sulfonate, alkyl aryl Sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate salt, alkyl aryl phosphate, styryl aryl Phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl phosphate Anionic surfactants of salts and naphthalene sulfonate formaldehyde condensates; such as sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polyglycerides, fatty acid alcohol polyglycol ethers, acetylene glycol, acetylene alcohol, oxygen extenders Alkyl block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl aryl ether, polyoxyethylene glycol alkyl ether, polyethylene glycol, polyoxyethylene fatty acid ester, Non-ionic surfactants of polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxypropylene fatty acid ester; olive oil, kapok seed oil, castor oil, palm Vegetable oils such as oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil, liquid paraffin, mineral oil, etc. As for each component of these adjuvants, as long as it does not deviate from the purpose of the present invention, one kind or two or more kinds can be selected as appropriate. In addition to the aforementioned adjuvants, they can also be appropriately selected and used from the adjuvants known in the art. For example, extenders, tackifiers, anti-settling agents, antifreeze agents, dispersion stabilizers, and medicines can also be used. Harm reduction agents, mildew inhibitors and other commonly used auxiliary agents. The blending ratio (weight ratio) of the compound of the present invention and various adjuvants is 0.001:99.999-95:5, ideally 0.005:99.995-90:10. When actually using these preparations, they can be used directly, or they can be diluted to a predetermined concentration with a diluent such as water, and various developing agents (surfactants, vegetable oils, mineral oils, etc.) can be added as needed.

The application of the compound of the present invention will vary depending on the weather conditions, formulation form, application time, application site, types of pests, occurrence conditions, etc., and cannot be generalized, generally it is 0.05 to 800,000 ppm, ideally 0.5 The active ingredient concentration of -500,000 ppm is carried out, and the application amount of the compound of the present invention per unit area is 0.05 to 50,000 g per 1 hectare, preferably 1 to 30,000 g. In addition, methods of controlling pests, mites, nematodes, or soil pests using such application methods, especially methods of controlling plant parasitic mites, agricultural pests, and plant parasitic nematodes using such application methods are also included in this Invented.

The application of various formulations of the pest control agent containing the compound of the present invention as an active ingredient, or a dilution thereof, can generally use a general application method, that is, it can be dispersed (for example, spray, misting, atomization) (atomizing), particle dispersion, water surface application, etc.), soil application (mixing, infusion, etc.), surface application (coating, powder coating, coating, etc.), immersion of poison bait, etc. In addition, the aforementioned active ingredients may be mixed in the feed and fed to livestock, thereby suppressing the generation and growth of harmful insects, especially harmful insects in the excrement of domestic animals. In addition, it can also be applied by a so-called ultra low volume application method. For this method, it can contain 100% of the active ingredient.

In addition, the agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides containing the compound of the present invention as an active ingredient can be mixed or used together with other pesticides, fertilizers, pesticide harm reducing agents, etc., in this case Sometimes it will show more excellent effect and effectiveness. Other pesticides may include herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, and the like. In particular, an insecticidal composition, an acaricidal composition, a nematicidal composition or a soil pesticidal composition obtained by mixing or combining the compound of the present invention with one or more active ingredient compounds of other pesticides It can be improved in a better direction in the scope of application, the time of drug treatment, and the control activity. In addition, the compounds of the present invention and the active ingredient compounds of other pesticides can be prepared separately and mixed for application, or both can be prepared together and used. Such an insecticidal composition, acaricidal composition, nematicidal composition or soil insecticidal composition is also included in the present invention.

農(diazinon)、陶斯松(chlorpyrifos)、甲基陶斯松(chlorpyrifos‐methyl)、毆殺松(acephate)、普硫松(prothiofos)、福賽絕(fosthiazate)、加奪松(cadusafos)、乙拌磷(dislufoton)、加福松(isoxathion)、異丙胺磷(isofenphos)、愛殺松(ethion)、乙氧嘧啶磷(etrimfos)、喹硫磷(quinalphos)、二甲基亞硝胺(dimethylvinphos)、樂果原藥(dimethoate)、硫丙磷(sulprofos)、硫滅松(thiometon)、繁米松(vamidothion)、白克松(pyraclofos)、必芬松(pyridaphenthion)、亞特松(pirimiphos-methyl)、丙蟲磷(propaphos)、松必爽粉(phosalone)、福木松(formothion)、馬拉松(malathion)、殺蟲畏(tetrachlorvinphos)、毒蟲畏(chlorfenvinphos)、殺螟晴(cyanophos)、敵百蟲(trichlorfon)、殺撲磷(methidathion)、稻豐散(phenthoate)、ESP(異亞碸磷，oxydeprofos)、谷速松(azinphos-methyl)、芬殺松(fenthion)、飛達松(heptenophos)、甲氧氯(methoxychlor)、巴拉松(parathion)、磷克(phosphocarb)、滅賜松(demeton-S-methyl)、亞素靈(monocrotophos)、達馬松(methamidophos)、imicyafos、甲基巴拉松(parathion-methyl)、托福松(terbufos)、福賜米松(phosphamidon)、益滅蝨(phosmet)、福瑞松(phorate)、辛硫磷(phoxim)、三唑磷(triazophos)之有機磷酸酯系化合物； 如加保利(carbaryl)、安丹(propoxur)、得滅克(aldicarb)、加保扶(carbofuran)、硫敵克(thiodicarb)、納乃得(methomyl)、歐殺滅(oxamyl)、乙硫苯威(ethiofencarb)、比加普(pirimicarb)、丁基滅必蝨(fenobucarb)、丁基加保扶(carbosulfan)、免扶克(benfuracarb)、免敵克(bendiocarb)、線威(furathiocarb)、異丙威(isoprocarb)、速滅威(metolcarb)、滅殺威(xylylcarb)、XMC(3,5-二甲苯基甲基胺甲酸酯，3,5-xylyl methylcarbamate)、芬硫克(fenothiocarb)之胺甲酸酯系化合物； 如培丹(cartap)、硫賜安(thiocyclam)、免速達(bensultap)、殺蟲單(thiosultap-sodium)、殺蟲雙(thiosultap-disodium)、殺蟲單(monosultap)、殺蟲雙(bisultap)、殺蟲環草酸鹽(thiocyclam hydrogen oxalate)之沙蠶毒素衍生物； 如大克蟎(dicofol)、得脫蟎(tetradifon)、硫丹(endosulfan)、得氯蟎(dienochlor)、地特靈(dieldrin)之有機氯系化合物； 如芬布賜(fenbutatin oxide)、錫蟎丹(cyhexatin)之有機金屬系化合物； 如芬化利(fenvalerate)、百滅寧(permethrin)、賽滅寧(cypermethrin)、溴氰菊酯(deltamethrin)、賽洛寧(cyhalothrin)、七氟菊酯(tefluthrin)、醚菊酯(ethofenprox)、三氟醚菊酯(flufenprox)、氟氯氰菊酯(cyfluthrin)、芬普寧(fenpropathrin)、護賽寧(flucythrinate)、氟胺氰菊酯(fluvalinate)、乙氰菊酯(cycloprothrin)、益洛寧(lambda-cyhalothrin)、除蟲菊精(pyrethrins)、氰戊菊酯(esfenvalerate)、胺菊酯(tetramethrin)、苄呋菊酯(resmethrin)、對氯二苯醚(protrifenbute)、聯苯菊酯(bifenthrin)、六氯氰菊酯(zeta-cypermethrin)、阿納寧(acrinathrin)、亞滅寧(alpha-cypermethrin)、亞烈寧(allethrin)、精高效氯氟氰菊酯(gamma-cyhalothrin)、反式氯氰菊酯(theta-cypermethrin)、福化利(tau-fluvalinate)、四溴菊酯(tralomethrin)、丙氟菊酯(profluthrin)、高效氯氰菊酯(beta-cypermethrin)、貝他賽扶寧(beta-cyfluthrin)、美特寧(metofluthrin)、酚丁滅寧(phenothrin)、氟氯苯菊酯(flumethrin)、溴氰菊酯(decamethrin)之除蟲菊系化合物； 如二福隆(diflubenzuron)、克福隆(chlorfluazuron)、氟苯脲(teflubenzuron)、氟芬隆(flufenoxuron)、殺鈴脲(triflumuron)、六伏隆(hexaflumuron)、祿芬隆(lufenuron)、雙苯氟脲(novaluron)、多氟脲(noviflumuron)、雙三氟蟲脲(bistrifluron)、啶蜱脲(fluazuron)之苯甲醯基脲系化合物； 如美賜平(methoprene)、百利賽芬(pyriproxyfen)、苯氧威(fenoxycarb)、苯蟲醚(diofenolan)之保幼激素之化合物； 如畢達本(pyridaben)之噠

酮系化合物； 如芬普蟎(fenpyroximate)、芬普尼(fipronil)、吡蟎胺(tebufenpyrad)、乙蟲清(ethiprole)、唑蟲醯胺(tolfenpyrad)、乙醯蟲腈(acetoprole)、吡

氟蟲腈(pyrafluprole)、吡啶氟蟲腈(pyriprole)之吡唑系化合物； 如益達胺(imidacloprid)、烯啶蟲胺(nitenpyram)、啶蟲脒(acetamiprid)、噻蟲啉(thiacloprid)、賽速安(thiamethoxam)、可尼丁(clothianidin)、呋蟲胺(nidinotefuran)、達特南(dinotefuran)、硝蟲噻

(nithiazine)之新菸鹼系化合物； 如蟲醯肼(tebufenozide)、甲氧蟲醯肼(methoxyfenozide)、環蟲醯胺(chromafenozide)、氯蟲醯肼(halofenozide)之肼系化合物； 如啶蟲丙醚(pyridalyl)、佛尼胺(flonicamid)之吡啶系化合物； 如螺蟎酯(spirodiclofen)、螺甲蟎酯(spiromesifen)、螺蟲乙酯(spirotetramat)、spiropidion之環狀酮烯醇系化合物； 如嘧蟎酯(fluacrypyrim)之嗜球果傘素(strobilurin)系化合物； 如嘧蟲胺(flufenerim)之吡啶胺(pyridinamine)系化合物； 二硝系化合物、有機硫化合物、脲系化合物、三

系化合物、腙(hydrazone)系化合物、及其他化合物，如flometoquin、布芬淨(buprofezin)、合賽多(hexythiazox)、雙甲脒(amitraz)、殺蟲脒(chlordimeform)、氟矽菊酯(silafluofen)、唑蚜威(triazamate)、派滅淨(pymetrozine)、畢汰芬(pyrimidifen)、克凡派(chlorfenapyr)、因得克(indoxacarb)、亞醌蟎(acequinocyl)、依殺蟎(etoxazole)、賽滅淨(cyromazine)、1,3-二氯丙烯(1,3-dichloropropene)、丁醚脲(diafenthiuron)、異噻蟲唑(benclothiaz)、聯苯胼酯(bifenazate)、毆蟎多(propargite)、克芬蟎(clofentezine)、氰氟蟲腙(metaflumizone)、氟蟲醯胺(flubendiamide)、丁氟蟎酯(cyflumetofen)、氯蟲醯胺(chlorantraniliprole)、氰蟲醯胺(cyantraniliprole)、環溴蟲醯胺(cyclaniliprole)、腈吡蟎酯(cyenopyrafen)、氟蟲吡喹(pyrifluquinazon)、芬殺蟎(fenazaquin)、磺胺蟎酯(amidoflumet)、氟蟲胺(sulfluramid)、愛美松(hydramethylnon)、聚乙醛(metaldehyde)、蘭尼鹼(ryanodine)、增效炔醚(verbutin)、氯苯甲酸酯(chlorobenzoate)、噻唑基肉桂腈(thiazolylcinnanonitrile)、碸蟲啶(sulfoxaflor)、氟噻蟲碸(fluensulfone)、三氟苯嘧啶(triflumezopyrim)、afidopyropen、flupyradifuron、fluxametamide、氟氰蟲醯胺(tetraniliprole)、fluralaner、broflanilide、pyflubumide、dicloromezotiaz、fluhexafon、tioxazafen、fluazaindolizine、acynonapyr、benzpyrimoxan、oxazosulfyl、flupyrimin、tyclopyrazoflor之化合物等。 再者，本發明化合物亦可與下列物質混用、併用：如蘇力菌鮎澤亞種(Bacillus thuringiensis aizawai)、蘇力菌庫斯克亞種(Bacillus thuringiensis kurstaki)、Bacillus thuringiensis israelensis、Bacillus thuringiensis japonensis、Bacillus thuringiensis tenebrionis等Bacillus thuringiensis所生成之結晶蛋白毒素、昆蟲病原病毒劑、昆蟲病原線狀菌劑、線蟲病原線狀菌劑等之微生物農藥；如阿維菌素(avermectin)、因滅汀苯甲酸鹽(emamectin Benzoate)、密滅汀(milbemectin)、倍脈心(milbemycin)、多殺菌素(spinosad)、害獲滅(ivermectin)、殺蟎菌素(lepimectin)、DE-175、阿巴汀(abamectin)、因滅汀(emamectin)、賜諾特(spinetoram)之抗生素及半合成抗生素；如印楝素(azadirachtin)、魚藤酮(rotenone)之天然物；如避蚊胺(deet)之忌避劑等。The active ingredient compounds of insecticides, acaricides, nematicides, or soil insecticides (general names; including a part of which are still in the application, or the test code of the Japan Plant Disease Control Association) among the other pesticides mentioned above, for example, such as cloth Profenofos, dichlorvos, fenamiphos, fenitrothion, EPN (phenyl thiophosphonic acid (O-ethyl-O-4-nitrophenyl) ester, O- ethyl O-4-nitrophenyl phenylphosphonothioate), two

Diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiofos, fosthiazate, cadusafos, and ethyl phosphorus (dislufoton), isofathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, le Dimethoate, sulprofos, thiometon, vamidothion, pyraclofos, pyridaphenthion, pirimiphos-methyl, propion Propaphos, phosalone, formothion, malathion, tetrachlorvinphos, chlorfenvinphos, cyanophos, trichlorfon ( trichlorfon), methidathion, phenthoate, ESP (oxydeprofos), azinphos-methyl, fenthion, heptenophos, Methoxychlor, parathion, phosphocarb, demeton-S-methyl, monocrotophos, methamidophos, imicyafos, methylbarba Organic phosphoric acid of parathion-methyl, terbufos, phosphamidon, phosmet, phorate, phoxim, triazophos Ester 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, 3,5-xylyl methylcarbamate), fenthiocarb (fenothiocarb) carbamate compounds; such as cartap, thiocyclam (thiocyclam) ), bensultap, thiosultap-sodium, thiosultap-disodium, thiosultap-disodium, monosultap, bisultap, thiocyclam hydrogen oxalate ) Of nervosa toxin derivatives; such as diclofen, tetradifon, endosulfan, endosulfan, dienochlor, and dieldrin; such as fen Organometallic compounds of fenbutatin oxide and cyhexatin; such as fenvalerate, permethrin, cypermethrin, deltamethrin, and cypermethrin Cyhalothrin, tefluthrin, ethofenprox, flufenprox, cyfluthrin, fenpropathrin, flucythrinate, fluoride Fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrins, esfenvalerate, tetramethrin, and benfurfur Resmethrin, protrifenbute, bifenthrin, zeta-cypermethrin, acrinathrin, alpha-cypermethrin, and alenin ( allethrin), refined lambda-cyhalothrin (gamma-cyhalothrin), trans-cypermethrin (theta-cypermethrin), and fuauli (tau- fluvalinate), tralomethrin, profluthrin, beta-cypermethrin, beta-cyfluthrin, metofluthrin, phenbutrazine ( Pyrethroid compounds of phenothrin, flumethrin, and decamethrin; such as diflubenzuron, chlorfluazuron, teflubenzuron, flufen Flufenoxuron, triflumuron, hexaflumuron, lufenuron, novaluron, noviflumuron, bistrifluron, Benzoyl urea compounds of fluazuron; such as metopine, meriprene, pyriproxyfen, fenoxycarb, diofenolan juvenile hormone compounds ; Such as Pyridaben (pyridaben)

Ketone compounds; such as fenpyroximate, fipronil, tebufenpyrad, ethiprole, tolfenpyrad, acetoprole, pyrimidine

Pyrazole compounds of pyrafluprole and pyriprole; such as imidacloprid, nitenpyram, acetamiprid, thiacloprid, Thiamethoxam, clothianidin, nidinotefuran, dinotefuran, nitrocarbazone

(nithiazine) neonicotinoid compounds; such as tebufenozide, methoxyfenozide, chromafenozide, halofenozide hydrazine compounds; such as acetamiprid Pyridine compounds of pyridalyl and flonicamid; such as spirodiclofen, spiromesifen, spirotetramat, spiropidion cyclic ketoenol compounds ; Strobilurin compounds such as fluacrypyrim; pyridinamine compounds such as flufenerim; dinitro compounds, organic sulfur compounds, urea compounds, tris

Compounds, hydrazone compounds, and other compounds, such as flototoquin, buffefene (buprofezin), hexythiazox, amitraz, chlordimeform, flumethrin ( silafluofen), triazamate, pymetrozine, pyrimidifen, chlorfenapyr, indoxacarb, acequinocyl, etoxazole ), cyromazine, 1,3-dichloropropene, 1,3-dichloropropene, diafenthiuron, benclothiaz, bifenazate, and mite (propargite), clofentezine, metaflumizone, flubendiamide, cyflumetofen, chlorantraniliprole, cyantraniliprole , Cyclaniliprole, cyenopyrafen, cyenopyrafen, pyrifluquinazon, fenazaquin, amidoflumet, sulfluramid, and emezon ( hydramethylnon, metaldehyde, ryanodine, verbutin, chlorobenzoate, thiazolylcinnanonitrile, sulfoxaflor, fluorine Fluensulfone, triflumezopyrim, afidopyropen, flupyradifuron, fluxametamide, tetraniliprole, fluralaner, broflanilide, pyflubumide, dicloromezotiaz, fluhexafon, tioxazapy, pyrozindolizine, fluazainol Flupyrimin, tyclopyrazoflor compounds, etc. . Furthermore, the compounds of the present invention can also be used in combination with the following substances: Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus Microbial pesticides such as crystalline protein toxins produced by Bacillus thuringiensis such as thuringiensis tenebrionis, insect pathogenic virus agents, insect pathogenic nematodes, nematode pathogenic nematodes; eg avermectin, indetectin benzoic acid Salt (emamectin Benzoate), milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE-175, abatin ( abamectin), emamectin, spinetoram antibiotics and semi-synthetic antibiotics; such as azadirachtin, rotenone natural substances; such as deet repellent, etc. .

系化合物； 如比芬諾(pyrifenox)之吡啶系化合物； 如芬瑞莫(fenarimol)之甲醇(carbinol)系化合物； 如苯銹啶(fenpropidin)之哌啶系化合物； 如芬普福(fenpropimorph)、三得芬(tridemorph)之

啉系化合物； 如三苯羥錫(fentin hydroxide)、三苯醋錫(fentin acetate)之有機錫系化合物； 如戊菌隆(pencycuron)之脲系化合物； 如達滅芬(dimethomorph)、氟

啉(flumorph)之桂皮酸系化合物； 如乙霉威(diethofencarb)之胺甲酸苯酯系化合物； 如咯菌腈(fludioxonil)、拌種咯(fenpiclonil)之氰吡咯系化合物； 如亞托敏(azoxystrobin)、克收欣(kresoxim‐methyl)、苯氧菌胺(metominostrobin)、三氟敏(trifloxystrobin)、啶氧菌酯(picoxystrobin)、肟醚菌胺(oryzastrobin)、醚菌胺(dimoxystrobin)、百克敏(pyraclostrobin)、氟嘧菌酯(fluoxastrobin)之嗜球果傘素(strobilurin)系化合物； 如㗁唑菌酯(famoxadone)之㗁唑啶二酮系化合物； 如韓樂寧(ethaboxam)之噻唑羧醯胺系化合物； 如丙森鋅(iprovalicarb)、苯噻菌胺(benthiavalicarb-isopropyl)之纈氨醯胺系化合物； 如N-(異丙氧基羰基)-L-纈胺醯基-(3RS)-3-(4-氯苯基)-β-丙胺酸甲酯(valiphenalate)之醯基胺基酸系化合物； 如咪唑菌酮(fenamidone)之咪唑啶酮系化合物； 如環醯菌胺(fenhexamid)之羥基醯胺苯系化合物； 如氟硫滅(flusulfamide)之苯碸醯胺系化合物； 如賽芬胺(cyflufenamid)之肟醚系化合物； 蒽醌系化合物； 巴豆酸系化合物； 如維利黴素(validamycin)、嘉賜黴素(kasugamycin)、保粒黴素(polyoxins)之抗生素； 如克熱淨(iminoctadine)、多寧(dodine)之胍系化合物； 如6-第三丁基-8-氟-2,3-二甲基喹啉-4-基乙酸酯(異丁乙氧喹啉(tebufloquin))之喹啉系化合物； 如(Z)-2-(2-氟-5-(三氟甲基)苯硫基)-2-(3-(2-甲氧苯基)噻唑啶-2-亞基)乙腈(噻唑烷(flutianil))之噻唑啶系化合物； 其他化合物，如苯卡布(pyribencarb)、亞賜圃(isoprothiolane)、百快隆(pyroquilon)、速滅淨(diclomezine)、快諾芬(quinoxyfen)、普拔克(propamocarb hydrochloride)、氯化苦(chloropicrin)、邁隆(dazomet)、斯美地(metam‐sodium)、白克列(nicobifen)、滅芬農(metrafenone)、UBF-307、雙氯氰菌胺(diclocymet)、丙氧喹啉(proquinazid)、安美速(amisulbrom；別名amibromdole)、3-(2,3,4-三甲氧基-6-甲基苯甲醯基)-5-氯-2-甲氧基-4-甲基吡啶、4-(2,3,4-三甲氧基-6-甲基苯甲醯基)-2,5-二氯-3-三氟甲基吡啶、甲氧苯啶菌(pyriofenone)、異非他米多(isofetamid)、雙炔醯菌胺(mandipropamid)、氟吡菌胺(fluopicolide)、環丙醯菌胺(carpropamid)、消蟎普(meptyldinocap)、葚孢菌素(spiroxamine)、胺苯吡菌酮(fenpyrazamine)、mandestrobin、ZF-9646、BCF-051、BCM-061、BCM-062等。The active ingredient compounds (common names; including a part of which are still in the application, or the test code of the Japan Plant Disease Control Association) in the above other pesticides can be exemplified by examples such as mepanipyrim, pyrimethanil, cyper Anilinopyrimidine compounds of cyprodinil and ferimzone; such as 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6- Trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine triazolopyrimidine-based compounds; such as fuazinam (fluazinam) pyridylamine-based compounds; such as triadimefon ), bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil , Cyproconazole, tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, four Tetraconazole, oxpoconazole fumarate, sipconazole, prothioconazole, triadimenol, flutriafol, difnoconazole ), fluquinconazole, fenbuconazole, bromuconazole, diniconazole, tricyclazole, probenazole, simeconazole, rice Azole compounds of pefurazoate, ipconazole, and imibenconazole; such as quinoline compounds of quinomethionate; such as maneb and zineb ), mancozeb, polycarbamate, metiram, methyl zinc propineb, thiram dithiamine carbamate compounds; such as heat Bishalide, chlorotha lonil), organochlorine compounds of quintozene; such as benomyl, cyazofamid, thiophanate-methyl, carbendazim, Imidazole compounds of thiabendazole and fuberiazole; cyanoacetamide compounds of cymoxanil; such as metalaxyl, metalaxyl-M, Mefenoxam, oxadixyl, ofurace, benalaxyl, benalaxyl-M, alias kiralaxyl, chiralaxyl, furalaxyl , Cyprofuram, carboxin, oxycarboxin, thifluzamide, boscalid, bixafen, isothiobacillus Anilide compounds of isothianil, tiadinil, sedaxane; sulfonamide compounds of dichlofluanid; such as copper (II) (cupric hydroxide), organic copper (oxine copper) copper compounds; such as hymexazol (hymexazol) isoxazole compounds; such as forese (fosetyl-Al), tolclofos-methyl (tolclofos-methyl), sulfur Phosphoric acid (S-benzyl-O,O-diisopropyl) ester, dithiophosphoric acid (O-ethyl-S,S-diphenyl) ester, ethyl aluminum hydrophosphate, edifenphos ), organophosphorus compounds of iprobenfos; such as captan, captafol, folpet phthalimide compounds; such as procymidone, Iprodione and vinclozolin dicarboxamide compounds; such as flutolanil and mepronil benzamide compounds; such as penthiopyrad ), 3-(difluoromethyl)-1-methyl-N-[(1RS,4SR,9RS)-1,2,3,4-tetrahydro-9-isopropyl-1,4-methyl bridge Naphthalene-5-yl]pyrazole-4-carboxamide and 3-(difluoromethyl)-1-methyl-N-[(1RS,4SR,9SR)-1 , A mixture of 2,3,4-tetrahydro-9-isopropyl-1,4-methylnaphth-5-yl]pyrazole-4-carboxamide (isopyrazam), silothia Acetamide-based compounds of silthiopham, fenoxanil, furametpyr; such as benzamide-based compounds of fluopyram and zoxamide; Piper as triforine

Compounds; such as pyrifenox pyridine compounds; such as fenarimol (fenarimol) methanol (carbinol) compounds; such as fenpropidin (fenpropidin) piperidine compounds; such as fenpropimorph (fenpropimorph) Of tridentmorph

Porphyrin compounds; organic tin compounds such as fentin hydroxide and fentin acetate; urea compounds such as pencycuron; dimethomorph and fluorine

Cinnamic acid compounds of flumorph; such as phenyl carbamate compounds of diethofencarb; cyanopyrrole compounds of fludioxonil and fenpiclonil; such as yatomin ( azoxystrobin), kresoxim-methyl, metominostrobin, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin, Strobilurin compounds of pyraclostrobin and fluoxastrobin; such as oxazolidinedione compounds of famoxadone; thiazole carboxylates of ethoxaboxam Acetamide-based compounds; Valinamide-based compounds such as iprovalicarb and benthiavalicarb-isopropyl; eg N-(isopropoxycarbonyl)-L-valamine amide-(3RS )-3-(4-chlorophenyl)-β-alanine methyl ester (valiphenalate) amide amino acid compounds; such as imidazolidone (fenamidone) imidazolidinone compounds; such as cyproteril ( fenhexamid) hydroxyamide benzene compounds; such as flusulfamide (flusulfamide) phenanthrene amide compounds; such as cyflufenamid (cyflufenamid) oxime ether compounds; anthraquinone compounds; crotonic acid compounds; such as vitamins Antibiotics such as validamycin, kasugamycin, and polyoxins; guanidine compounds such as iminoctadine and dodine; such as 6-third butyl Quinoline compounds of -8-fluoro-2,3-dimethylquinolin-4-yl acetate (isobuethloquinoline (tebufloquin); such as (Z)-2-(2-fluoro- 5-(trifluoromethyl)phenylthio)-2-(3-(2-methoxyphenyl)thiazolidine-2-ylidene)acetonitrile (flutianil) thiazolidine compounds; other compounds , Such as pyribencarb, isoprothiolane, pyroquilon, diclomezine, quinoxyfen, propamocarb hydrochloride, chloropicrin , Myzo (dazomet), Sri Lanka Metam-sodium, nicobifen, metrafenone, UBF-307, diclocymet, proquinazid, amisulbrom; alias amibomdole ), 3-(2,3,4-trimethoxy-6-methylbenzyl)-5-chloro-2-methoxy-4-methylpyridine, 4-(2,3,4- (Trimethoxy-6-methylbenzyl)-2,5-dichloro-3-trifluoromethylpyridine, pyriofenone, isofetamid, diacetylene Mandipropamid, fluopicolide, carpropamid, meptyldinocap, spiroxamine, fenpyrazamine, mandestrobin, ZF -9646, BCF-051, BCM-061, BCM-062, etc.

Other pesticides that can be mixed or used with the compounds of the present invention include, for example, the active ingredient compounds of herbicides described in The Pesticide Manual (17th Edition).

Hereinafter, several preferred embodiments of the substituted pyridine compound of the present invention or a salt thereof will be exemplified, but the present invention is not limited to these. (1) A substituted pyridine compound or its salt, represented by the aforementioned formula (I). (2) The substituted pyridine compound or the salt thereof according to (1), wherein R ¹ is a hydrogen atom, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group or an alkylcarbonyl group. (3) The substituted pyridine compound or the salt thereof according to (1) or (2), wherein R ¹ is a hydrogen atom, an alkyl group, a haloalkyl group, an alkoxy group or an alkylcarbonyl group. (4) The substituted pyridine compound or a salt thereof according to any one of (1) to (3), wherein R ² is an alkyl group, a haloalkyl group, an alkoxy group, an alkylthio group, an alkylsulfinyl group , Alkylsulfonyl or dialkylamine. (5) The substituted pyridine compound or a salt thereof according to any one of (1) to (4), wherein R ² is an alkyl group, a haloalkyl group, or an alkoxy group. (6) The substituted pyridine compound or a salt thereof according to any one of (1) to (5), wherein R ³ is a hydrogen atom or an alkyl group. (7) The substituted pyridine compound or a salt thereof according to any one of (1) to (6), wherein R ³ is an alkyl group. (8) The substituted pyridine compound or the salt thereof according to any one of (1) to (7), wherein R ⁴ is nitro, alkyl, alkoxy, alkylthio, alkylcarbonyl, alkoxy Carbonyl, (alkylthio)carbonyl or carboxyl. (9) The substituted pyridine compound or a salt thereof according to any one of (1) to (8), wherein R ⁴ is an alkoxycarbonyl group. (10) The substituted pyridine compound or its salt according to any one of (1) to (9), wherein m is 0 or 1.

(11) A pest control agent containing the substituted pyridine compound represented by the aforementioned formula (I') or a salt thereof as an effective ingredient. (12) The pest control agent according to (11), wherein R ¹ is a hydrogen atom, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group or an alkylcarbonyl group. (13) The pest control agent according to (11) or (12), wherein R ¹ is a hydrogen atom, an alkyl group, a haloalkyl group, an alkoxy group or an alkylcarbonyl group. (14) The pest control agent according to any one of (11) to (13), wherein R ² is alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfinyl, alkyl Sulfonyl or dialkylamino. (15) The pest control agent according to any one of (11) to (14), wherein R ² is an alkyl group, a haloalkyl group or an alkoxy group. (16) The pest control agent according to any one of (11) to (15), wherein R ³ is a hydrogen atom or an alkyl group. (17) The pest control agent according to any one of (11) to (16), wherein R ³ is an alkyl group. (18) The pest control agent according to any one of (11) to (17), wherein R ^{4′ is nitro} , alkyl, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl , (Alkylthio) carbonyl or carboxyl. (19) (11) to (18) according to any one of the pest control agent, wherein, R ^{4 'is} an alkoxycarbonyl group. (20) The pest control agent according to any one of (11) to (19), wherein m is 0 or 1. (21) An insecticide, acaricide, nematicide, or soil insecticide for agriculture and horticulture, containing the compound or salt thereof according to any one of (11) to (20) as an active ingredient. (22) An insecticide for agriculture and horticulture, containing the compound or salt thereof according to any one of (11) to (20) as an active ingredient. (23) A method for controlling pests by applying an effective amount of a compound such as any one of (11) to (20) or a salt thereof to control pests. [Example]

The embodiments of the present invention are described below, but the present invention is not limited to these and explained. First, the synthesis examples of the compounds of the present invention are described.

Synthesis Example 1 Synthesis of 4-(2-(trifluoromethyl)pyrimidine-5-carboxamide) nicotinic acid methyl ester (Compound No. Ia-5) 2-(trifluoromethyl)pyrimidine-5-carboxylic acid (0.25g), 4-amino-nicotinic acid methyl ester (0.20g), O-(7-azabenzotriazol-1-yl )-N,N,N',N'-tetramethylurea hexafluorophosphate (0.60g), triethylamine (0.55mL) was dissolved in tetrahydrofuran (3.0mL) and stirred at room temperature for 18 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the solvent was distilled off under reduced pressure. The residue was purified by flash chromatography (eluent: n-heptane/ethyl acetate) to obtain the target product (0.24 g, yield 56%).

-2-羧醯胺)菸鹼酸甲酯(化合物No.Ib-5)之合成 使5-(三氟甲基)吡

-2-羧酸(0.11g)、4-胺基-菸鹼酸甲酯(80mg)、O-(7-氮雜苯并三唑-1-基)-N,N,N’,N’-四甲基脲六氟磷酸鹽(0.40g)、三乙胺(0.22mL)溶於N,N-二甲基甲醯胺(3.5mL)並於室溫攪拌24小時。將反應混合物投入水中，並以乙酸乙酯進行萃取。對於有機層以飽和食鹽水進行洗淨，加入無水硫酸鈉進行乾燥。利用過濾去除無水硫酸鈉後，於減壓下餾去溶劑。將殘渣利用急速層析(洗提液：正庚烷/乙酸乙酯)予以精製，獲得目的物(90mg，產率52%)。Synthesis Example 2 4-(5-(trifluoromethyl)pyridine

-2-Carboxamide) methyl nicotinic acid (Compound No. Ib-5) is synthesized by 5-(trifluoromethyl)pyridine

-2-carboxylic acid (0.11g), 4-amino-nicotinic acid methyl ester (80mg), O-(7-azabenzotriazol-1-yl)-N,N,N',N' -Tetramethylurea hexafluorophosphate (0.40 g) and triethylamine (0.22 mL) were dissolved in N,N-dimethylformamide (3.5 mL) and stirred at room temperature for 24 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the solvent was distilled off under reduced pressure. The residue was purified by flash chromatography (eluent: n-heptane/ethyl acetate) to obtain the target product (90 mg, yield 52%).

-2-羧醯胺)菸鹼酸甲酯(化合物No.Ib-10)之合成 對於使5-(三氟甲基)吡

-2-羧酸(0.10g)溶於四氫呋喃(5mL)而得之溶液，於0℃添加草醯氯(0.13mL)及1滴之N,N-二甲基甲醯胺。將該反應混合物於室溫攪拌2小時。 然後，於減壓下除去其溶劑及過量的試藥。使其固體殘渣再次溶解於四氫呋喃(5mL)，並於室溫下予以滴加至使4-(甲基胺基)菸鹼酸甲酯(70mg)與三乙胺(0.58mL)溶於四氫呋喃(7mL)而得之溶液中。將該反應混合物於加熱回流下攪拌12小時。於反應混合物加入飽和碳酸氫鈉水溶液後，以乙酸乙酯進行萃取。對於有機層以飽和食鹽水進行洗淨，加入無水硫酸鈉進行乾燥。利用過濾去除無水硫酸鈉後，於減壓下餾去溶劑。將殘渣利用急速層析(洗提液：正庚烷/乙酸乙酯)予以精製，獲得目的物(0.12g，產率68%)。Synthesis Example 3 4-(N-methyl-5-(trifluoromethyl)pyridine

-2-Carboxyamido)nicotinic acid methyl ester (Compound No.Ib-10) Synthesis of 5-(trifluoromethyl)pyridine

A solution obtained by dissolving -2-carboxylic acid (0.10 g) in tetrahydrofuran (5 mL) was added oxalyl chloride (0.13 mL) and 1 drop of N,N-dimethylformamide at 0°C. The reaction mixture was stirred at room temperature for 2 hours. Then, the solvent and excess reagent were removed under reduced pressure. The solid residue was dissolved in tetrahydrofuran (5mL) again and added dropwise at room temperature until 4-(methylamino)nicotinic acid methyl ester (70mg) and triethylamine (0.58mL) were dissolved in tetrahydrofuran ( 7mL) in the resulting solution. The reaction mixture was stirred under heating and refluxing for 12 hours. After adding a saturated sodium bicarbonate aqueous solution to the reaction mixture, extraction was performed with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the solvent was distilled off under reduced pressure. The residue was purified by flash chromatography (eluent: n-heptane/ethyl acetate) to obtain the target product (0.12 g, yield 68%).

The representative examples of the compounds of the present invention are listed in Table 1 and Table 2 below. Moreover, these compounds can be synthesized based on the aforementioned synthesis examples or the aforementioned various production methods. In Table 1 and Table 2, the numerical values described in the physical properties column indicate the melting point (°C), and the compounds described as "NMR" are shown in Tables 3 to 6 in ¹ H-NMR spectral data. In addition, No. in Table 1 to Table 6 represents the compound number. In the table, Me represents methyl, Et represents ethyl, n-Pr represents n-propyl, t-Bu represents third butyl, i-Pr represents isopropyl, c-Pr represents cyclopropyl, n-Bu Represents n-butyl, i-Bu represents isobutyl, and s-Bu represents second butyl. In addition, for example, a compound described as "4-Me" in the column of (R ² ) _m means that only the substitution position given in the chemical structural formula in the table is substituted with R ² , that is, only the 4 position is substituted with a "M=1" based compounds. On the other hand, the compound described as "m=0" means a compound that is not substituted with R ² . Other similar records are also compared here.

【Table 1】

【Table 2】

【table 3】

【Table 4】

【table 5】

【Table 6】

【Table 7】

【Table 8】

【Table 9】

【Table 10】

【Table 11】

Test Example 1 Effect test on brown planthopper Rice seedlings were immersed in a chemical solution prepared in such a manner that the concentration of the compound of the present invention became 200 ppm. After the drug solution is air-dried, wrap the roots with a damp absorbent cotton and put it in a test tube. In it, put about 10 2 to 3 instar larvae of brown planthopper, cover the mouth of the tube with gauze, and let stand in a constant temperature room with lighting at 25℃. After 5 days of treatment, the life and death of the brown planthopper was determined, and the insect mortality rate (%) was determined according to the following calculation formula. In addition, the aforementioned compound Nos. Ia-5, Ia-10, Ia-12, Ia-26, Ia-52, Ia-55, Ia-56, Ia-64, Ia-65, Ia-66, Ia-69 were used , Ia-71, Ib-1, Ib-3, Ib-5, Ib-6, Ib-8, Ib-10, Ib-12, Ib-17, Ib-47, Ib-61, Ib-62, Ib -67, Ib-70, Ib-73, Ib-76, Ib-97, Ib-98, Ib-99, Ib-100, Ib-113 as the compounds of the present invention, all compounds exhibited more than 90% of insect deaths rate.

Insect mortality (%) = (number of dead insects/number of released insects) × 100

Test Example 2 Effect test on tobacco whitefly Put tobacco whitefly adults into potted cucumber seedlings. Let it spawn for 1 day, then take out the cucumber seedlings and let them stand in a constant temperature room with lighting at 25°C. After 7 days, the number of 1-2 instar larvae parasitizing cucumber seedlings was investigated, and the drug solution prepared in such a way that the concentration of the compound of the present invention became 200 ppm was sprayed with a hand sprayer. After the drug solution is air-dried, it is allowed to stand in a constant temperature room with lighting at 25°C. After 7 days of treatment, the number of old larvae was investigated, and the control value was calculated according to the following calculation formula. In addition, the aforementioned compound Nos. Ia-3, Ia-5, Ia-10, Ia-12, Ia-17, Ia-25, Ia-26, Ia-28, Ia-49, Ia-56, Ia-63 are used , Ia‐64, Ia‐65, Ia‐66, Ia‐67, Ia‐69, Ia‐71, Ia‐73, Ia‐74, Ib‐1, Ib‐5, Ib‐6, Ib‐8, Ib ‐10, Ib‐12, Ib‐17, Ib‐47, Ib‐61, Ib‐62, Ib‐67, Ib‐70, Ib‐73, Ib‐97, Ib‐98, Ib‐99, Ib‐100 , Ib-113 as the compound of the present invention, all compounds show a control value of 90 or more.

Prevention value = (1-(Ta×Cb)/(Tb×Ca))×100 Ta: Number of old larvae after treatment of cucumber seedlings Tb: the number of larvae of the first and second instars before the treatment of cucumber seedlings Ca: Number of old larvae of untreated cucumber seedlings after treatment Cb: the number of larvae of the first and second instars of untreated cucumber seedlings before treatment

Test Example 3 Effect test on Myzus persicae Five adult peach aphids were placed on the radish leaves that had been inserted into the test tube with water. One day later, the adult insects were removed, and then the number of larvae parasitic on the radish leaves was counted and subjected to a dipping treatment in a drug solution prepared in such a manner that the concentration of the compound of the present invention became 200 ppm. After the drug solution is air-dried, it is allowed to stand in a constant temperature room with lighting at 25°C. After 5 days of treatment, the life and death of the green peach aphid is determined, and the mortality rate of the insect is determined according to the following calculation formula. In addition, detached and abnormal insects are regarded as dead insects. In addition, the aforementioned compounds No. Ia-3, Ia-5, Ia-6, Ia-8, Ia-10, Ia-12, Ia-17, Ia-25, Ia-26, Ia-28, Ia-52 are used , Ia-56, Ia-63, Ia-64, Ia-65, Ia-66, Ia-67, Ia-69, Ia-71, Ia-73, Ib-1, Ib-3, Ib-5, Ib ‐6, Ib‐8, Ib‐10, Ib‐12, Ib‐17, Ib‐47, Ib‐49, Ib‐52, Ib‐61, Ib‐62, Ib‐67, Ib‐70, Ib‐73 , Ib-76, Ib-97, Ib-98, Ib-99, Ib-100, Ib-113, Ib-114 as the compounds of the present invention, all compounds exhibited an insect mortality rate of more than 90%.

Insect mortality (%) = (number of dead insects/number of tested insects) × 100

In addition, in Test Example 3 above, Compound No. Ib-114 (the compound represented by the aforementioned formula (C)) exhibited an insect mortality rate of 90% or more, but the compound represented by the aforementioned formula (A) and the aforementioned formula (B) represented The compounds did not show effect.

The preparation examples are described below.

Preparation Example 1 (1) The compound of the present invention: 20 parts by weight (2) Clay: 70 parts by weight (3) White carbon 　 5 parts by weight (4) Sodium polycarboxylate: 3 parts by weight (5) Sodium alkylnaphthalene sulfonate 2 parts by weight The above materials are mixed uniformly to make a hydrating agent.

Preparation Example 2 (1) Compound of the present invention 　5 parts by weight (2) Talc: 60 parts by weight (3) Calcium carbonate 34.5 parts by weight (4) Flowing paraffin 　0.5 parts by weight The above materials are uniformly mixed to make a powder.

Preparation Example 3 (1) The compound of the present invention: 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 materials are uniformly mixed and dissolved to make an emulsion.

Preparation Example 4 (1) Clay: 68 parts by weight (2) 2 parts by weight of sodium lignosulfonate (3) Polyoxyethylene alkyl aryl sulfate 　 5 parts by weight (4) White carbon 　 25 parts by weight The mixture of the above components and the compound of the present invention are mixed in a weight ratio of 4:1 to prepare a hydrating agent.

Preparation Example 5 (1) The compound of the present invention 　50 parts by weight (2) Formaldehyde condensate of sodium alkylnaphthalene sulfonate 2 parts by weight (3) Polysilicone oil 　0.2 parts by weight (4) 47.8 parts by weight of water In the stock solution obtained by uniformly mixing and crushing the above substances, further add (5) Sodium polycarboxylate 　5 parts by weight (6) Anhydrous sodium sulfate 42.8 parts by weight And evenly mix, granulate, and dry to make granule hydrating agent.

Preparation Example 6 (1) Compound of the present invention 　5 parts by weight (2) Polyoxyethylene octyl phenyl ether 　 1 part by weight (3) Polyoxyethylene alkyl ether phosphate 　 0.1 parts by weight (4) Granular calcium carbonate 　93.9 parts by weight After uniformly mixing (1) to (3) in advance and diluting with an appropriate amount of acetone, spray (4) to remove acetone to prepare granules.

Preparation Example 7 (1) The compound of the present invention: 2.5 parts by weight (2) N,N-dimethylacetamide 　 2.5 parts by weight (3) 95.0 parts by weight of soybean oil The above materials are uniformly mixed and dissolved to make an ultra low volume formulation.

Preparation Example 8 (1) The compound of the present invention: 10 parts by weight (2) Diethylene glycol monoethyl ether 　80 parts by weight (3) Polyoxyethylene alkyl ether 　 10 parts by weight The above ingredients are uniformly mixed to make a liquid preparation.

The present invention has been described in detail and with reference to specific embodiments, but it is obvious to those skilled in the art that various changes and modifications can be added without departing from the spirit and scope of the present invention. This application is based on the Japanese patent application filed on February 22, 2018 (Japanese Patent Application No. 2018-029492), and the contents thereof are incorporated herein by reference.

Claims (6)

A substituted pyridine compound or its salt is represented by formula (I);

In formula (I), A is a substituent represented by formula (A-1) or a substituent represented by formula (A-2); R ³ is a hydrogen atom, an alkyl group, an alkylcarbonyl group or an alkoxycarbonyl group; R ⁴ Nitro, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, (alkylthio)carbonyl or carboxy;

In formula (A-1) or formula (A-2), R ¹ is a hydrogen atom, alkyl group, haloalkyl group, alkoxy group, haloalkoxy group, alkylcarbonyl group, cycloalkyl group, cycloalkoxy group, Alkylthio, alkylsulfinyl, alkylsulfonyl or haloalkylthio; R ² is alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkyl Sulfonyl, alkylsulfonyl or dialkylamine; m is an integer from 0 to 2; when m is 2, R ² may be the same or different. For example, the substituted pyridine compound or its salt according to item 1 of the patent application, wherein, in the formula (I), R ³ is a hydrogen atom, an alkyl group, an alkylcarbonyl group or an alkoxycarbonyl group; R ⁴ is a nitro group or an alkyl group , Alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, (alkylthio)carbonyl or carboxy; in the formula (A-1) or the formula (A-2), R ¹ is hydrogen Atom, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylcarbonyl; R ² is alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfinyl, alkyl Sulfonyl or dialkylamine; m is 0 or 1. A pest control agent containing a substituted pyridine compound represented by formula (I') or a salt thereof as an effective ingredient;

In formula (I'), A is a substituent represented by formula (A-1) or a substituent represented by formula (A-2); R ³ is a hydrogen atom, an alkyl group, an alkylcarbonyl group or an alkoxycarbonyl group; R ^{4'is nitro} , halogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, (alkylthio)carbonyl or carboxy;

In formula (A-1) or formula (A-2), R ¹ is a hydrogen atom, alkyl group, haloalkyl group, alkoxy group, haloalkoxy group, alkylcarbonyl group, cycloalkyl group, cycloalkoxy group, Alkylthio, alkylsulfinyl, alkylsulfonyl or haloalkylthio; R ² is alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkyl Sulfonyl, alkylsulfonyl or dialkylamine; m is an integer from 0 to 2; when m is 2, R ² may be the same or different; ^however , ^when R ^{4'is bromine} , R ¹ Not a hydrogen atom. Pest control agent as claimed in item 3 of the patent scope, wherein, in the formula (I'), R ³ is a hydrogen atom, an alkyl group, an alkylcarbonyl group or an alkoxycarbonyl group; R ^{4'is a nitro group} , an alkyl group , Alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, (alkylthio)carbonyl or carboxy; in the formula (A-1) or the formula (A-2), R ¹ is hydrogen Atom, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylcarbonyl; R ² is alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfinyl, alkyl Sulfonyl or dialkylamine; m is 0 or 1. An insecticide, acaricide, nematicide, or soil insecticide for agriculture and horticulture, which contains a substituted pyridine compound or a salt thereof represented by formula (I') in item 3 or 4 of the patent application scope as an active ingredient. A method for controlling harmful organisms is to apply an effective amount of a substituted pyridine compound or a salt thereof represented by formula (I') in item 3 or 4 of the patent application scope to control harmful organisms.