Compound for insecticidal and acaricidal use, and use of compound

Abstract

Provided are a compound of formula I, an isomer thereof or a salt thereof, wherein the definitions of D, E, F, G, Q, X1, X2, X3, and X4 are as defined in the description. The compound exhibits excellent insecticidal and acaricidal effects, and has good application prospects.

Description

A compound for insecticidal and acaricidal use and its use TECHNICAL FIELD

[0001] The present application belongs to the field of pesticides, in particular to the field of insecticidal and acaricidal agents, and more particularly relates to a novel insecticidal and acaricidal agent compound and its use, and a pesticide composition containing the compound. BACKGROUND

[0002] In crop production in agriculture and horticulture, the loss caused by pests is still very large, and various effective insecticidal compounds have been developed in the prior art. However, continuous use is prone to drug resistance, and there is a strong need to develop new active compounds, especially compounds with excellent effects, for insecticidal and acaricidal agents. The present application provides a novel insecticidal and acaricidal compound with a novel structure, which can efficiently kill insects and acarids at a low concentration. SUMMARY

[0003] The present application aims to provide an acaricidal agent with safe and efficient acaricidal properties at a low concentration for agricultural and horticultural plants. The present inventors have conducted in-depth research to achieve the above-mentioned purpose, and as a result, it has been found that an imidazole compound or a salt thereof having a specific structure has excellent acaricidal activity and exhibits good characteristics and safe and efficient acaricidal agents.

[0004] The present application provides a compound of formula I, a stereoisomer, a nitroxide compound or a salt thereof,

[0005] wherein,

[0006] E, E, F, G are each independently selected from N or CR2;

[0007] Q is NR1, O or S;

[0008] X1, X2, X3, X4 are each independently selected from H, halogen, CN, NO2, C1-C 10 alkyl and halogen C1-C 10 alkyl;

[0009] Y is selected from S, S=O, O=S=O or R3-N=S=O;

[0010] R1 is selected from H, CN, optionally substituted C1-C 10 alkyl, optionally substituted C3-C 10 cycloalkyl, optionally substituted C1-C 10 alkoxy, halogen C3-C 10 cycloalkoxy, optionally substituted C2-C 10 alkenyl, optionally substituted C2-C 10alkynyl, optionally substituted C1-C 10 alkylcarbonyl, optionally substituted C1-C 10 alkoxycarbonyl, optionally substituted arylcarbonyl, optionally substituted aryloxycarbonyl;

[0011] R2is selected from the group consisting of H, halogen, CN, NO2, C1-C 10 alkyl and halogenated C1-C 10 alkyl and halogenated C1-C

[0012] R3is selected from the group consisting of H, C1-C 10 alkyl and halogenated C1-C 10 alkyl and halogenated C1-C

[0013] Preferably, formula I is formula II,

[0014] wherein D, E, F, G, Q, Y, X1, X2, X3, X4and R1are as defined above.

[0015] Preferably, formula I is formula III,

[0016] wherein D, E, F, G, Q, Y, X1, X2, X3and X4are as defined above.

[0017] Preferably, formula I is formula IV

[0018] wherein D, E, F, G, Q, Y, X1, X2, X3and X4are as defined above.

[0019] The present application also provides a pesticidal composition containing the compound of formula I, its stereoisomer or salt thereof as an effective active ingredient.

[0020] The present application also provides a method for controlling pests and mites in agriculture. Advantageous effects

[0021] 1. The compound of the present application has an excellent insecticidal and miticidal effect, and can show an excellent control effect even at a low concentration. DETAILED DESCRIPTION

[0022] In order to make the objects, technical solutions and advantages of the embodiments of the present application clearer, the technical solutions in the embodiments of the present application will be described clearly and completely below. Obviously, the described embodiments are some but not all of the embodiments of the present application. Based on the embodiments of the present application, all other embodiments obtained by those of ordinary skill in the art without creative effort should fall into the scope of the present application. Unless otherwise explicitly indicated, in the entire specification and claims, the term "comprise" or its variants such as "contain" or "include" should be understood as including the stated components or steps, but not excluding the presence of other components or steps.

[0023] In addition, in order to better illustrate the present application, numerous specific details are given in the following specific embodiments.

[0024] Those skilled in the art should understand that the present application can be implemented without certain specific details. In some embodiments, the raw materials, methods, means and the like which are well known to those skilled in the art are not described in detail, so as to highlight the main idea of the present application.

[0025] In order to make the objects, technical solutions and advantages of the embodiments of the present application clearer, the technical solutions in the embodiments of the present application will be described clearly and completely below. Obviously, the described embodiments are some but not all of the embodiments of the present application. Based on the embodiments of the present application, all other embodiments obtained by those of ordinary skill in the art without creative effort should fall into the scope of the present application. Unless otherwise explicitly indicated, in the entire specification and claims, the term "comprise" or its variants such as "contain" or "include" should be understood as including the stated components or steps, but not excluding the presence of other components or steps.

[0026] In addition, in order to better illustrate the present application, numerous specific details are given in the following specific embodiments.

[0027] Those skilled in the art should understand that the present application can be implemented without certain specific details. In some embodiments, the raw materials, methods, means and the like which are well known to those skilled in the art are not described in detail, so as to highlight the main idea of the present application.

[0028] When the compounds of the present application can exist in the form of tautomers, the compounds described above and below are understood to include the corresponding tautomeric forms, if applicable, even if these tautomeric forms are not explicitly mentioned in each case.

[0029] If the compounds of the formula I according to the application have one or more chiral centers and thus exist as enantiomers or diastereomers, it is possible to use pure enantiomers, racemates, diastereomers in the compositions according to the application.

[0030] Any asymmetric atom (e.g. carbon) of the compounds according to the application can exist in the form of a racemate or enantiomerically enriched, e.g. in the form of (R)-, (S)- or (R,S)-configurational forms

[0031] If the compounds of the formula I according to the application have functional groups which can be ionized, they can also be used in the form of their agriculturally suitable salts or mixtures thereof. The salts according to the application can be inorganic salts such as hydrochlorides, hydrobromides, sulfates, nitrates, phosphates and the like, but are not limited thereto. Also, the salts can be organic acid salts such as formates, acetates, oxalates, fumarates, methanesulfonates, benzenesulfonates and the like, but are not limited thereto.

[0032] The term "alkyl" (as well as the alkyl moieties of other groups comprising alkyl, such as haloalkyl) as used herein denotes in each occurrence straight-chain or branched alkyl groups having usually from 1 to 20 carbon atoms, often from 1 to 10 carbon atoms, preferably from 1 to 6 carbon atoms, in particular from 1 to 4 carbon atoms. Examples of C1-C4alkyl are methyl, ethyl, n-propyl, i-propyl, n-butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (i-butyl), 1,1-dimethylethyl (tert-butyl). Examples of C1-C6alkyl are, in addition to the groups mentioned under C1-C4alkyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl.

[0033] Halogen in the present application is usually fluorine, chlorine, bromine or iodine, preferably fluorine, bromine or chlorine. Correspondingly, this also applies to halogen in connection with other structures, such as haloalkyl. Haloalkyl preferably has a chain length of 1 to 6 carbon atoms, more preferably a chain length of 1 to 4 carbon atoms. Examples of haloalkyl are, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably fluoromethyl, difluoromethyl, trifluoromethyl, trichloromethyl, difluorochloromethyl and dichlorofluoromethyl.

[0034] When the groups related to the present application are substituted, the substituents can be halogen, cyano, C1-C 10 alkyl, halo C1-C 10 alkyl, C3-C 10 cycloalkyl, halo C1-C 10 cycloalkyl, C1-C 10 alkoxy, halo C1-C 10 alkoxy, halo C3-C 10 cycloalkyl and halo C3-C 10 cycloalkoxy and the like, but are not limited thereto.

[0035] In the present application, aryl is preferably phenyl and naphthyl.

[0036] The present application provides a compound of formula I or a salt thereof or an isomer thereof,

[0037] wherein,

[0038] D, E, F, G are independently selected from N or CR2,

[0039] X1, X2, X3, X4are independently selected from H, halogen, CN, NO2, C1-C 10 alkyl and halo C1-C 10 alkyl;

[0040] Y is selected from S, S=O, O=S=O or R3-N=S=O;

[0041] Q is NR1, O or S;

[0042] R1is selected from H, CN, optionally substituted C1-C 10 alkyl, optionally substituted C3-C 10 cycloalkyl, optionally substituted C1-C 10 alkoxy, halo C3-C 10 cycloalkoxy, optionally substituted C2-C 10 alkenyl, optionally substituted C2-C 10 alkynyl, optionally substituted C1-C 10 alkylcarbonyl, optionally substituted C1-C 10 alkoxycarbonyl, optionally substituted arylcarbonyl, optionally substituted aryloxycarbonyl;

[0043] R2is selected from H, halogen, CN, NO2, C1-C 10 alkyl and halo C1-C 10 alkyl;

[0044] R3is selected from H, C1-C 10alkyl and halogenated C1-C6 alkyl, in particular preferably one of H, halogen, methyl, ethyl, propyl, butyl, monofluoromethyl, difluoromethyl and trifluoromethyl; 10 alkyl and halogenated C1-C6 alkyl, in particular preferably one of H, halogen, methyl, ethyl, propyl, butyl, monofluoromethyl, difluoromethyl and trifluoromethyl;

[0045] Preferably, in one set of technical solutions,

[0046] D, E, F, G are independently selected from CR2, R2is selected from H, halogen, CN, NO2, C1-C6 alkyl and halogenated C1-C6 alkyl, in particular preferably one of H, C1-C6 alkyl and halogenated C1-C6 alkyl, more particularly preferably one of H, halogen, methyl, ethyl, propyl, butyl, monofluoromethyl, difluoromethyl and trifluoromethyl;

[0047] X1, X2, X3, X4are independently selected from H, halogen, C1-C6 alkyl and halogenated C1-C6 alkyl, in particular preferably one of H, halogen, methyl, ethyl, propyl, butyl, monofluoromethyl, difluoromethyl and trifluoromethyl;

[0048] Y is selected from S, S=O or O=S=O;

[0049] R1is selected from H, C1-C6 alkyl and halogenated C1-C6 alkyl, in particular preferably one of H, methyl, ethyl, propyl, butyl, monofluoromethyl, difluoromethyl and trifluoromethyl;

[0050] Preferably, in another set of technical solutions,

[0051] D is N, E, F, G are independently selected from CR2, R2is selected from H, halogen, CN, NO2, C1-C6 alkyl and halogenated C1-C6 alkyl, in particular preferably one of H, C1-C6 alkyl and halogenated C1-C6 alkyl, more particularly preferably one of H, halogen, methyl, ethyl, propyl, butyl, monofluoromethyl, difluoromethyl and trifluoromethyl; 10 alkyl and halogenated C1-C6 alkyl, in particular preferably one of H, halogen, methyl, ethyl, propyl, butyl, monofluoromethyl, difluoromethyl and trifluoromethyl; 10 alkyl and halogenated C1-C6 alkyl, in particular preferably one of H, halogen, methyl, ethyl, propyl, butyl, monofluoromethyl, difluoromethyl and trifluoromethyl;

[0052] X1, X2, X3, X4are independently selected from H, halogen, C1-C6 alkyl and halogenated C1-C6 alkyl, in particular preferably one of H, halogen, methyl, ethyl, propyl, butyl, monofluoromethyl, difluoromethyl and trifluoromethyl;

[0053] Y is selected from S, S=O or O=S=O;

[0054] R1is selected from H, C1-C6 alkyl and halogenated C1-C6 alkyl, in particular preferably one of H, methyl, ethyl, propyl, butyl, monofluoromethyl, difluoromethyl and trifluoromethyl;

[0055] Preferably, formula I is formula II,

[0056] wherein D, E, F, G, X1, X2, X3, X4, Y, R1and R2are as defined above in relation to formula I;

[0057] Preferably, formula I is formula III,

[0058] wherein D, E, F, G, X1, X2, X3, X4, Y, R1and R2are as defined above in relation to formula I;

[0059] Preferably, formula I is formula IV

[0060] wherein D, E, F, G, X1, X2, X3, X4, Y, R1and R2are as defined above in relation to formula I;

[0061] Preferably, the compound of the application is a compound of Table 1 below

[0062] Table 1 Compounds of the application

[0063] The application also provides a process for the preparation of a compound of formula II, the synthetic route of which is as follows:

[0064] wherein D, E, F, G, Y, X1, X2, X3, X4and R1are as defined in relation to formula I,

[0065] which specifically comprises the following steps:

[0066] In a solvent, in the presence of a basic substance and a condensing agent, compound I-4 and compound I-5 are subjected to a first reaction to give compound I-6;

[0067] In a solvent, the compound I-6 and an acidic substance are subjected to a second reaction to give compound I-7;

[0068] In a solvent, in the presence of a basic substance, the compound I-7 and a compound R1-L, wherein L is a leaving group, preferably a halogen, are subjected to a third reaction to give compound I-10;

[0069] In a solvent, in the presence of an oxidizing agent, the compound I-10 is reacted to give compound II.

[0070] The application also provides another process for the preparation of a compound of formula II, the synthetic route of which is as follows:

[0071] wherein D, E, F, G, Y, X1, X2, X3, X4 and R1 are defined as described above in the description.

[0072] It specifically comprises the following steps:

[0073] reacting compound I-4 and compound I-8 in a solvent in the presence of a basic substance and a condensing agent to obtain compound I-9;

[0074] reacting compound I-9 and an acidic substance in a solvent to obtain compound I-10;

[0075] reacting compound I-10 in a solvent in the presence of an oxidizing agent to obtain compound I.

[0076] The application also provides a preparation of formula III, and a synthetic route thereof is as follows:

[0077] wherein D, E, F, G, Y, X1, X2, X3, X4 are defined as described above in the description.

[0078] It specifically comprises the following steps:

[0079] reacting compound I-4 and compound I-11 in a solvent in the presence of a basic substance and a condensing agent to obtain compound I-12;

[0080] reacting compound I-12 and an acidic substance in a solvent to obtain compound I-13;

[0081] reacting compound I-13 in a solvent in the presence of an oxidizing agent to obtain compound III.

[0082] The application also provides a preparation of formula IV, and a synthetic route thereof is as follows:

[0083] wherein D, E, F, G, Y, X1, X2, X3, X4 are defined as described above in the description,

[0084] It specifically comprises the following steps:

[0085] reacting compound I-4 and compound I-14 in a solvent in the presence of a basic substance and a condensing agent to obtain compound I-15;

[0086] reacting compound I-15 and an acidic substance in a solvent to obtain compound I-16;

[0087] reacting compound I-16 in a solvent in the presence of an oxidizing agent to obtain compound IV.

[0088] The solvent in the above preparation method refers to water or an organic solvent, which can be a polar solvent or a non-polar solvent, for example, diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, DMF, DMA, NMP, dioxane, dichloromethane, dichloroethane, chloroform, carbon tetrachloride, benzene, xylene, nitrobenzene, chlorobenzene, dichlorobenzene, etc., but not limited thereto. The above solvent can be mixed with one or more.

[0089] The base in the above preparation method can be an inorganic base or an organic base, for example, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, potassium hydroxide, sodium hydroxide, sodium hydride, potassium hydride, etc., but not limited thereto. The organic base can be, for example, methylamine, dimethylamine, trimethylamine, triethylamine, diisopropylamine, diethylmethylamine, diisopropylethylamine, sodium formate, potassium formate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, DBU, etc., but not limited thereto. The above base can be mixed with one or more.

[0090] The acid in the above preparation method can be an inorganic acid or an organic acid, for example, hydrochloric acid, nitric acid, sulfuric acid, hydrobromic acid, phosphoric acid, etc., but not limited thereto. The organic acid can be, for example, formic acid, acetic acid, propionic acid, oxalic acid, trifluoroacetic acid, trichloroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, benzoic acid, p-toluenesulfonic acid, etc., but not limited thereto.

[0091] The oxidant in the above preparation method is hydrogen peroxide, peroxobenzoic acid, m-chloroperbenzoic acid, etc., but not limited thereto.

[0092] The condensing agent in the above preparation method is a condensing agent commonly used in the art, for example, EDC, EDCI, CDI, DCC, HATU (2-(7-oxabenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate), etc., but not limited thereto.

[0093] The application also provides a preparation method of formula I-4, and the synthetic route is as follows:

[0094] wherein X1, X2, X3, X4, and X5 are defined as in formula I.

[0095] The first reaction of compound I-1 is carried out in a solvent in the presence of a nitrous substance and a thiocyanic compound to obtain compound I-2;

[0096] The reaction of compound I-2 is carried out in a solvent under basic conditions to obtain compound I-3;

[0097] The reaction of compound I-3 is carried out in a solvent in the presence of a basic substance to obtain compound I-4;

[0098] The solvent in the above preparation method refers to water or an organic solvent, which can be a polar solvent or a non-polar solvent, for example, diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, DMF, DMA, NMP, dioxane, dichloromethane, dichloroethane, chloroform, carbon tetrachloride, benzene, xylene, nitrobenzene, chlorobenzene, dichlorobenzene, and the like, but is not limited thereto. The above solvent can be mixed with one or more.

[0099] The base in the above preparation method can be an inorganic base or an organic base, for example, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, potassium hydroxide, sodium hydroxide, sodium hydride, potassium hydride, and the like, but is not limited thereto. The organic base can be, for example, methylamine, dimethylamine, trimethylamine, triethylamine, diisopropylamine, diethylmethylamine, diisopropylethylamine, sodium formate, potassium formate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, DBU, and the like, but is not limited thereto. The above base can be mixed with one or more.

[0100] The acid in the above preparation method can be an inorganic acid or an organic acid, for example, hydrochloric acid, nitric acid, sulfuric acid, hydrobromic acid, phosphoric acid, and the like, but is not limited thereto. The organic acid can be, for example, formic acid, acetic acid, propionic acid, oxalic acid, trifluoroacetic acid, trichloroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, benzoic acid, p-toluenesulfonic acid, and the like, but is not limited thereto.

[0101] The nitrous acid substance in the above preparation method is sodium nitrite, potassium nitrite, and the like, but is not limited thereto.

[0102] The thiocyanic acid compound in the above preparation method is one or more of KSCN, NaSCN, CuSCN, and FeSCN.

[0103] The present application also provides a composition comprising the compound of formula I, an isomer thereof, or a salt thereof as an active ingredient.

[0104] The present application also provides the use of the compound of formula I or a salt thereof or an isomer thereof and the composition of the present application in insecticidal and acaricidal applications. The composition comprises, in addition to the active ingredient, an agriculturally acceptable auxiliary ingredient selected from one or more of wetting agents, dispersants, emulsifiers, thickening agents, disintegrants, antifreezing agents, antifoaming agents, solvents, preservatives, stabilizers, synergists, or carriers.

[0105] The present application also provides a composition comprising at least one of the compound of formula I or a salt thereof and at least one auxiliary agent selected from surfactants, solid diluents, and liquid diluents.

[0106] Suitable solid carriers include natural or synthetic clays and silicates, e.g. natural silicas and diatomaceous earths; magnesium silicates, e.g. talc; aluminum magnesium silicates, e.g. kaolin, kieselguhr, montmorillonite and mica; white carbon, calcium carbonate, light calcium carbonate; calcium sulfate; limestone; sodium sulfate; ammonium salts, such as ammonium sulfate, hexamethylenediamine and urea, and the like.

[0107] Liquid carriers include water and organic solvents, and organic solvents can also be used as adjuvants or antifreeze additives when water is used as the solvent or diluent. Useful liquid gaseous fillers or carriers are those that are liquid at standard temperature and pressure, such as aerosol propellants, e.g. halocarbons, and also butane, propane, nitrogen and carbon dioxide, and the like.

[0108] Suitable organic solvents include aromatic hydrocarbons, e.g. benzene, xylene, toluene, and the like; chlorinated hydrocarbons, e.g. chlorobenzene, vinyl chloride, trichloromethane, dichloromethane, and the like; aliphatic hydrocarbons, e.g. petroleum fractions, cyclohexane, light mineral oil; alcohols, e.g. isopropyl alcohol, butanol, ethylene glycol, glycerol and cyclohexanol, and the like; and ethers and esters thereof; ketones, e.g. acetone, cyclohexanone, and dimethylformamide and N-methyl-pyrrolidone, vegetable oils, e.g. soybean oil, rapeseed oil and cottonseed oil, and the like.

[0109] Suitable surface-active agents (adjuvants, emulsifiers, dispersants, protective colloids, wetting agents and adhesion agents) include all customary ionic and non-ionic substances, such as ethoxylated nonylphenols, polyalkylene glycol ethers of linear or branched alcohols, reaction products of alkylphenols with ethylene oxide and / or propylene oxide, reaction products of fatty acid amines with ethylene oxide and / or propylene oxide, and fatty acid esters, alkylsulfonates, alkylsulfates, alkyl ether sulfates, alkyl ether phosphates, aryl sulfates, ethoxylated arylalkylphenols, such as tristyryl-phenol-ethoxylates, and ethoxylated and propoxylated arylalkylphenols, such as sulfated and phosphated arylalkylphenol-ethoxylates and -ethoxyl- and -propoxylates. Further examples are natural and synthetic water-soluble polymers, such as lignosulfonates, gelatin, gum arabic, phospholipids, starch, hydrophobically modified starch and cellulose derivatives, in particular cellulose esters and cellulose ethers, and polyvinyl alcohol, polyvinyl acetate, polyvinylpyrrolidone, polyacrylic acid, polymethacrylic acid and copolymers of (meth)acrylic acid and (meth)acrylic esters, and copolymers of methacrylic acid and methacrylic esters neutralized with alkali metal hydroxides, and condensates of optionally substituted naphthalenesulfonic acid with formaldehyde. The presence of a surface-active agent is necessary if one of the active ingredients and / or one of the inert carriers is not water-soluble and application is to be carried out in water.

[0110] The compositions according to the application can be prepared into suitable formulations by means of the methods generally used in the art. For example, the active substances are mixed with liquid solvents and / or solid carriers, while adding, if appropriate, surfactants such as emulsifiers, dispersants, stabilizers, wetters, further auxiliaries such as binders, antifoams, foam formers, antioxidants, crystallization inhibitors, viscosity regulators, suspending agents, spray droplet adjuvants, colorants, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, dispersants, thickeners, freezing-point depressants, antimicrobials, and the like.

[0111] The compositions according to the application can be applied in the form of their formulations or the use forms prepared therefrom, such as aerosols, capsule suspensions, cold-fogging concentrates, hot-fogging concentrates, encapsulated granules, fine granules, flowable concentrates for the treatment of seed, ready-to-use solutions, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, macrogranules, microgranules, oil-dispersible powders, oil-miscible flowable concentrates, oil-miscible liquids, gases (under pressure), gas-generating products, foams, pastes, suspension concentrates, suspo-emulsion concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, dusts and granules, water-soluble and water-dispersible granules or tablets, water-soluble or water-dispersible powders for the treatment of seed, wettable granules, active-substance-impregnated natural products and synthetic substances, and also microencapsulations in polymeric substances and seed-coating materials, and also ULV (ultra low volume) cold-fogging and hot-fogging formulations.

[0112] The compositions according to the application can also contain further components, such as further fungicides, insecticides, herbicides, plant growth regulators, attractants, acaricides, nematicides, fertilizers, safeners and the like, which can be formulated together with liquid or solid, granular fertilizer carriers, such as ammonium nitrate, urea and the like, or mixed with fine sand or soil.

[0113] The treatment of the plants and plant parts according to the application with the compositions comprising the compounds according to the application can be carried out directly or by action on their surroundings, habitat or storage space by the customary treatment methods, for example by immersing, spraying, atomizing, irrigating, evaporating, dusting, fogging, spreading-on, foaming, painting-on, coating-on, watering (drenching), instilling, for plant propagation material, in particular for seeds, also by dry seed treatment, wet seed treatment, slurry treatment, encrusting, coating with one or more layers and the like. It is also possible to exploit the active substances effectively by super-low-volume methods or by injecting formulations comprising the compounds according to the application or the compounds according to the application themselves into the soil.

[0114] When the compound of the present application is used in agriculture, the content of the compound of the present application or its salt in the preparation is preferably 0.01 to 90% by weight, more preferably 0.05 to 85% by weight. An agricultural acaricide in the form of wettable powder, emulsion, suspension, water suspension, water-soluble powder, water-dispersible granules can be diluted with water to a prescribed concentration to form a solution, suspension or emulsion and applied to plants or soil. In addition, an agricultural acaricide in the form of powder or granules can be directly applied to plants or soil. In addition, an epidemic control acaricide in the form of emulsion, wettable powder, water suspension, etc. can be diluted with water to a prescribed concentration for application. In addition, an epidemic control acaricide in the form of oil, aerosol, smoke, bait, acaricide sheet, etc. can be used directly. When the acaricide of the present application is used for the control of animal parasitic mites of livestock such as cattle and pigs, pets such as dogs and cats, the compound of the present application can be used at a rate of 0.01 to 1000 mg per 1 kg of host animal. The acaricide for animal parasitic mite control can be applied by a known veterinary method. As the method, for example, when systemic control is intended, a method in which the acaricide is administered to the animal by tablet, capsule, dipping liquid, mixed feed, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), etc. can be mentioned; when non-systemic control is intended, a method in which an oily or aqueous liquid preparation is administered by spraying, pour-on, spot-on, etc. can be mentioned; a method in which the acaricide is mixed in a resin, the mixture is molded into a suitable shape such as a collar or ear tag, and the same is worn by the animal, etc.

[0115] The compound of the present application exhibits excellent control effects on many mites, and has a good control effect at a concentration of 0.5 to 100 ppm. A preferred compound has a control effect of 100% or more at 10 ppm, and a more preferred compound also exhibits a very excellent effect of 50% or more at 1 ppm.

[0116] In order to expand the control target pests, extend the optimal control time or reduce the amount of the compound of the present application, the compound of the present application can be used in combination with other agricultural and horticultural insecticides and acaricides, nematocides, fungicides, biological pesticides, etc. and can also be used in combination with herbicides, plant growth regulators, fertilizers, etc. according to the use.

[0117] As other agricultural and horticultural insecticides, acaricides, nematicides for this purpose, for example, 3,5-xylyl methylcarbamate (XMC), fenobucarb (BPMC), Bt toxin class insecticidal compounds, chlorfenson (CPCBS), dichlorodiisopropyl ether (DCIP), 1,3-dichloropropene (D-D), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O-diethyl phosphorothioate (DSP), O-ethyl O-4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, acynonapyr, azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, abamectin, afidopyropen, avermectin-B, amidoflumet, amitraz, alanycarb, aldicarb, aldoxycarb, aldrin, alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, isazofos, isamidofos, isoamidofos, isoxathion, isocycloseram, isofenphos, isoprocarb: MIPC, epsilon-metofluthrin, epsilon-momfluorothrin, ivermectin, imicyafos, imidacloprid, imiprothrin, indoxacarb,S-cyanovalerate, ethiofencarb, ethion, ethiprole, etoxazole, ethofenprox, ethoprophos, etrimfos, emamectin, emamectin-benzoate, endosulfan, empenthrin, oxazosulfyl, oxamyl, oxydemeton-methyl, oxydeprofos: ESP, oxibendazole, oxfendazole, Potassium oleate, sodium oleate, cadusafos, kappa-tefluthrin, kappa-bifenthrin, cartap, carbaryl, carbosulfan, carbofuran, gamma-cyhalothrin, xylylcarb, quinalphos, kinoprene, chinomethionat, cloethocarb, clothianidin, clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyfos, chlordimeform, chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr, chlorfenson, ch1orfenvinphos, chlorfluazuron, chlorobenzilate, chlorobenzoate, chloroprallethrin, dicofol, salithion, cyhalodiamide, cyanophos: CYAP,diafenthiuron, diamidafos, cyantraniliprole, theta-cypermethrin, dienochlor, cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin, cyclaniliprole, dichlofenthion: ECP, cycloprothrin, dichlorvos: DDVP, dicloromezotiaz, disulfoton, dinotefuran, cyhalodiamide, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron, cyflumetofen, diflovidazin, cyhexatin, cypermethrin, dimethylvinphos, dimethoate, dimpropyridaz, dimefluthrin, silafluofen, cyromazine, spinetoram, spinosad, spirodiclofen, spirotetramat, spiropidion, spirodiclofen, spiroxamine, sulfluramid, sulprofos, sulfoxaflor, zeta-cypermethrin, diazinon, tau-fluvalinate, dazomet, thiacloprid, tiaxazafen, thiamethoxam, tioxazafen, thiodicarb, thiocyclam, thiosultap, thiosultap-sodium, thionazin,thiometon, deet, dieldrin, tetrachlorantraniliprole, tyclopyrazoflor, tetrachlorvinphos, tetradifon, tetraniliprole, tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin, teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, doramectin, tralopyril, tralomethrin, transfluthrin, triazamate, triazuron, trichlamide, trichlorphon (DEP), triflumezopyrium, triflumuron, tolfenpyrad, naled (BRP), nithiazine, nitenpyram, novaluron, noviflumuron, hydroprene, vaniliprole, vamidothion, parathion, parathion-methyl, halfenprox, halofenozide, bistrifluron, bisultap, hydramethylnon, hydroxypropyl starch, binapacryl, pyflubumide, bifenazate, bifenthrin, pymetrozine, pyraclorfos, pyrafluprole, pyridafenthion,pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methyl, pyrethrins, fipronil, fenazaquin, fenamiphos, bromopropylate, fenitrothion: MEP, fenoxycarb, fenothiocarb, phenothrin, fenobucarb, fensulfothion, fenthion: MPP, phenthoate: PAP, fenvalerate, fenpyroximate, fenpropathrin, fenbendazole, fosthiazate, formetanate, butathiofos, buprofezin, furathiocarb, prallethrin, fluacrypyrim, fluazaindolizine, fluazinam, fluazuron, fluensulfone, fluxametamide, flucycloxuron, flucythrinate, fluvalinate, flupyradifurone, flufiprole, flupyrazofos, flupyrimin, flufenerim, flufenoxystrobin, flufenoxuron, flufenzine, flufenoprox, fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flumethrin,flurimfen, prothiofos, protrifenbute, fonicamid, propaphos, propargite (BPPS), profenofos, broflanilide, profluthrin, propoxur (PHC), flometoquin, alpha-bromadiolone, bromopropylate, beta-cyfluthrin, hexaflumuron, hexythiazox, heptafluthrin, heptenophos, permethrin, benclothiaz, bendiocarb, benzpyrimoxan, bensultap, benzoximate, benfuracarb, phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet (PMP), polynactins, formetanate, formothion, phorate, machine oil, malathion, milbemycin, milbemycin-A, milbemectin, mecarbam, mesulfenfos, methomyl, metaldehyde, metaflumizone, methamidophos, metam-ammonium, metam-sodium, methiocarb, methidathion (DMTP), methylisothiocyanate, methylneodecanamide, methylparathion, metoxadiazone,methoxychlor, methoxyfenozide, metofluthrin, methoprene, metolcarb, meperfluthrin, mevinphos, monocrotophos, monosultap, momfluorothrin, lambda-cyhalothrin, ryanodine, lufenuron, rescalure, resmethrin, lepimectin, rotenone, levamisol hydrochloride, fenbutatin oxide, morantel tartarate, methyl bromide, cyhexatin, calcium cyanamide, calcium polysulfide, sulfur and nicotine-sulfate, and salts thereof.

[0118] As fungicides for agricultural horticulture used for the same purpose, for example, aureofungin, azaconazole, azithiram, acypetacs, acibenzoar, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, aminopyrifen, ampropylfos, ametoctradin, allyl alcohol, amisulbrom, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amicarbazole, amalcohol), 4-dodecyl-2,6-dimethylmorpholine (aldimorph), amobam, isotianil, isovaleridene, isopyrazam, isofetamid, isoflucypram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin, iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, metam, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, inpyrfluxam, uniconazole, uniconazole-P, echlomezole, edifenphos, etaconazole, ethaboxam, ethirimol, etem, ethoxyquin, etridiazole, enestroburin, enoxastrobin, epoxiconazole, oxadixyl, oxathiapiprolin, oxycarboxin, copper-8-quinolinolate, oxytetracycline, copper-oxinate, oxpoconazole, oxpoconazole-fumarate, oxolinic acid, oxycarboxin, oxytetracycline, copper-oxinate, oxpoconazole, oxpoconazole-fumarate, oxolinic acid, pefurazoate, pencycuron, pentachlorophenol, penthiopyrad, pentylsulfuric acid, pentachlorothio-phenyl ester, pentachlorophenol, penthiopyrad, pentylsulfuric acid, pentachlorothio-phenyl ester, pencycuron, penta- chlorophenol, penthiopyrad, pentylsulfuric acid, pentachlorothio-phenyl ester, pencycuron, penta-acid), octhilinone, ofurace, orysastrobin, metam-sodium, kasugamycin, carbamorph, carpropamid, carbendazim, carboxin, carvone, quinazamid, quinacetol, quinoxyfen, quinofumelin, chinomethionat, quinomethionate, captafol, captan, kiralaxyl, quinconazole, quintozene, guazatine, cufraneb, cuprobam, coumoxystrobin, glyodin, griseofulvin, climbazole, cresol, kresoxim-methyl, chlozolinate, clotrimazole, chlobenthiazone, chloraniformethan, chloranil, chlorquinox, chloropicrin, chlorfenazole, chlorodinitronaphthalene, chlorothalonil, chlorone b, salicylanilide, zarilamid, cyazofamid, diethyldithiocarbamic acid, dithianon, dodicin, dodemorph, dodemorph-acetate, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxamide, dodemorph-picoxpyrocarbonate), diethofencarb, cyclafuramid, diclocymet, dichlozoline, diclobutrazol, dichlofluanid, cycloheximide, dichlobentiazox, diclomezine, dicloran, dichlorophen, dichlone, disulfiram, ditalimfos, dithianon, diniconazole, R-diniconazole (diniconazole-M), zineb,

[0119] dinocap, dinocton, dinosulfon, dinoterbon, dinobuton, dinopenton, dipymetitrone, dipyrithione, diphenylamine, difenoconazole, cyflufenamid, diflumetorim, cyproconazole, cyprodinil, cyprofuram, cypendazole, simeconazole, dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, ziram, silthiofam, streptomycin, spiroxamine, sultropen, sedaxane, zoxamide, dazomet, thiadiazin, tiadinil, thiadifluor, thiabendazole, tioxymid, thioquinox, thiochlorfenphim, thiophanate, thiophanate-methyl, thifluzamide, thicyofen, thioquinox, thiram, decafentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid, tebuconazole, tebufloquin, dodicin, dodine, dodecylbenzenesulfonic acid diethylenediamine copper (II) salt (DBEDC), dodemorph, drazoxolon, triadimenol, triadimefon,triazbutil, triazoxide, triamiphos, triarimol, trichlamide, triclopyricarb, tricyclazole, triticonazole, tridemorph, tributyltin oxide, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolprocarb, natamycin, nabam, nitrostyrene, nitrothal-isopropyl, nuarimol, copper nonylphenolsulfonate, halacrinate, validamycin, valifenalate, harpin protein, picarbutrazox, bixafen, picoxystrobin, picobenzamide, pydiflumetofen, bithionol, bitertanol, hydroxyisoxazole, hydroisoxazole-potassium, binapacryl, biphenyl, piperalin, hymexazol, pyraoxystrobin, pyracarbolid, pyraclostrobin, pyraziflumid, pyrazophos, pyrapropoyne, pyrametostrobin, pyriofenone, pyridinitril, pyrifenox, pyrisoxazole, pyridachlometyl, pyrifenox, pyribencarb,pyriminostrobin, pyrimethanil, pyroxychlor, pyroxyfur, pyroquilon, vinclozolin, ferbam, famoxadone, fenapanil, fenamidone, fenaminosulf, fenaminstrobin, fenarimol, fenitropan, fenoxanil, ferimzone, ferbam, fentin, fenpiclonil, fenpicoxamid, fenpyrazamine, fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid, phthalide, buthiobate, butylamine, bupirimate, fuberidazole, blasticidin-S, furametpyr, furalaxyl, fluacrypyrim, fluazinam, fluindapyr, fluoxastrobin, fluoxapiprolin, fluotrimazole, fluopicolide, Fluopimomide, fluopyram, fluoroimide, furcarbanil, fluxapyroxad, fluquinconazole, furconazole, furconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, flufenoxystrobin, furfural, furmecyclox,flumetover, flumorph, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole, pronitridine, propamocarb, propiconazole, propineb, furophanate, probenazole, bromuconazole, florylpicoxamid, hexachlorobutadiene, hexaconazole, hexylthiofos, bethoxazin, benalaxyl, benalaxyl-M, benodanil, benomyl, perfurazoate, benquinox, penconazole, benzamorf, pencycuron, benzohydroxamic acid, benzovindiflupyr, bentaluron, benthiazole, benthiavalicarb, benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, phosdiphen, fosetyl, fosetyl-Al, polyoxins, polyoxorim, polycarbamate, folpet, formaldehyde, machine oil, maneb, mancozeb, mandipropamid, mandestrobin, myclozolin, myclobutanil, mildiomycin, milneb, mearbinzid, methasulfocarb, metazoxolon, metrafenone, metiram, metiram-zinc, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostrobin, metrafenone, metominostmetam, metam-sodium, metalaxyl, metalaxyl-M, metiram, methyl isothiocyanate, mepthyldinocap, metyltetraprole, metconazole, metsulfovax, methfuroxam, metominostrobin, metrafenone, mepanipyrim, mefenoxam, mefentrifluconazole, meptyldinocap, mepronil, mebenil, iodomethane, rabenzazole, methyl bromide, benzalkonium chloride, basic copper chloride, basic copper sulfate, silver, inorganic sterilizing agents such as the like, sodium hypochlorote, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate, sodium hydrogen carbonate, sulfur, copper sulfate anhydride, nickel dimethyldithiocarbamate, oxine copper, zinc sulfate, and copper sulfate pentahydrate, and salts thereof.

[0120] Also, as herbicides, for example, the following can be mentioned: 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA ethyl ester, MCPB, ioxynil, aclonifen, azafenidin, acifiuorfen, aziprotryne, azimsulfuron, asuam, acetochlor, atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid, amicarbazone, amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridione, ametryn, alachlor, allidochlor, alloxydim, alorac, iofensulfuron, isouron, isocarbamid, isoxachlortole, isoxapyrifop, isoxaflutole, isoxaben, isocil, isonoruron, isoproturon, isopropalin, isopolinate, isomethiozin, inabenfide, ipazine, ipfencarbazone, iprymidam, imazaquin, imazapic, imazapyr, imazamethapyr, imazamethabenz, imazamethabenz-methyl,imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolebutyric acid, uniconazole-P, eglinazine, esprocarb, ethametsulfuron, ethametsulfuron-methyl, ethalfluralin, ethiolate, ethychlozate ethyl, ethidimuron, etinofen, ethephon, ethoxysulfuron, ethoxyfen, etnipromid, ethofumesate, etobenzanid, epronaz, erbon, endothal, oxadiazon, oxadiargyl, oxaziclomefone, oxasulfuron, oxapyrazon, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb, cafenstrole, cambendichlor, carbasulam, carfentrazone, carfentrazone-ethyl, karbutilate, carbetamide, carboxazole, quizalofop, quizalofop-P, quizalofop-ethyl, xylachlor, quinoclamine, quinonamid, quinclorac, quinmerac, cumyluron, clacyfos, cliodinate, glyphosate, glufosinate,glufosinate-P, credazine, clethodim, cloxyfonac, clodinafop, clodinafop-propargyl, chlorotoluron, clopyralid, cloproxydim, cloprop, chlorbromuron, clofop, clomazone, chlomethoxynil, chlomethoxyfen, clomeprop, chlorazifop, chlorazine, cloransulam, chloranocryl, chloramben, cloransulam, cloransulam-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron, chlorthal, chlorthiamid, chlortoluron, chlornitrofen, chlorfenac, chlorfenprop, chlorbufam, chlorphthalim, chlorflurazole, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chloreturon, chloroxynil, chloroxuron, chlorotoluron, chloropon, saflufenacil, cyanazine, cyanatryn, di-allate, diuron, diethamquat, dicamba, cycluron, cycloate, cycloxydim, diclosulam,cyclosulfamuron, cyclopyranil, cyclopyrimorate, dichlorprop, dichlorprop-P, dichlobenil, diclofop, diclofop-methyl, dichlormate, dichloralurea, diquat, cisanilide, disul, siduron, dithiopyr, dinitramine, cinidon-ethyl, dinosam, cinosulfuron, dinoseb, dinoterb, dinofenate, dinoprop, cyhalofop-butyl, diphenamid, difenoxuron, difenopenten, difenzoquat, cybutryne, cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn, cypromid, cyperquat, gibberellin, simazine, dimexano, dimethachlor, dimidazon, dimethametryn, dimethenamid, simetryn, simeton, dimepiperate, dimefuron, cinmethylin, swep, sulglycapin, sulcotrione, sulfallate, sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl, secbumeton, sethoxydim,Other butylazine, terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyr, tiafenacil, thiencarbazone, thiencarbazone-methyl, tiocarbazil, tioclorim, thiobencarb, thidiazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmetryn, tetflupyrolimet, tetrafluron, thenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione, tembotrione, delachlor, terbacil, terbucarb, terbuchlor, terbuthylazine, terbutryn, topramezone, tralkoxydim, triaziflam, triasulfuron, triafamone, tri-allate, trietazine, tricamba, triclopyr, tridiphane, tritac, tritosulfuron, trifludimoxazin, triflusulfuron, triflusulfuron-methyl, trifluralin, trifloxysulfuron, tripropindan, tribenuron, tribenuron-methyl, trifop,trifopsime, trimeturon, tolpyralate, naptalam, naproanilide, napropamide, nicosulfuron, nitralin, nitrofen, nitrofluorfen, nipyraclofen, neburon, norflurazon, noruron, barban, paclobutrazol, paraquat, parafluron, haloxydine, halauxifen, haloxyfop, haloxyfop-P, haloxyfop-methyl, halosafen, halosulfuron, halosulfuron-methyl, bilanafos, bixlozone, picloram, picolinafen, bicyclopyrone, bispyribac, bispyribac-sodium, pydanon, pinoxaden, bifenox, piperophos, hymexazol, pyraclonil, pyrasulfotole, pyrazoxyfen, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazolate, bilanafos, pyraflufen-ethyl, pyriclor, pyridafol, pyrithiobac, pyrithiobac-sodium, pyridate, pyriftalid, pyributicarb, pyribenzoxim, pyrimisulfan, primisulfuron,pyriminobac-methyl, pyroxasulfone, pyroxsulam, fenasulam, phenisopham, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, phenothiol, fenoprop, phenobenzuron, fenquinotrione, fenthiaprop, fenteracol, fentrazamide, phenmedipham, phenmedipham-ethyl, butachlor, butafenacil, butamifos, buthiuron, buthidazole, butylate, buturon, butenachlor, butroxydim, butralin, butroxydim, flazasulfuron, flamprop, furyloxyfen, prynachlor, primisulfuron-methyl, fluazifop, fluazifop-P, fluazifop-butyl, fluazolate, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen, fluoromidine, flucarbazone, flucarbazone-sodium, fluchloralin, flucetosulfuron, fluthiacet, fiuthiacet-methyl,flupyrsulfuron, flufenacet, flufenican, flufenpyr, flupropacil, flupropanate, flupoxam, flumioxazin, flumiclorac, flumiclorac-pentyl, flumipropyn, flumezin, fluometuron, flumetsulam, fluridone, flurtamone, fluroxypyr, pretilachlor, proxan, proglinazine, procyazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, propanil, propyzamide, propisochlor, prohydrojasmon, propyrisulfuron, propham, profluazol, profluralin, prohexadione-calcium, propoxycarbazone, propoxycarbazone-sodium, profoxydim, bromacil, brompyrazon, prometryn, prometon, bromoxynil, bromofenoxim, bromobutide, bromobonil, florasulam, florpyrauxifen, hexachloroacetone, hexazinone, pethoxamid, benazolin, penoxsulam, pebulate,fluorodifen, fluchloralin, flumetralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flumeturon, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, flutolanil, flutriafol, flupoxam, flurprimidol, fluchloralin, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, flurazole, flurenol, fluridone, flurochloridone, fluroxmetobromuron, metobenzuron, methometon, metolachlor, metribuzin, mepiquat-chloride, mefenacet, mefluidide, monalide, monisouron, monuron, monochloroacetic acid, monolinuron, molinate, morfamquat, iodosulfuron, iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen, lancotrione, linuron, rimsulfuron, lenacil, rhodethanil, calcium peroxide and methyl bromide, and salts thereof.

[0121] In addition, the following can also be used in combination: Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusa sibirica, Phytoseiulus persimilis, Amblyseius cucumeris, Orius sauteri, and the like, natural enemy organisms, Beauveria brongniartii and the like, microbial pesticides, (Z)-10-tetradecenyl acetate, (E,Z)-4,10-tetradecadienyl acetate, (Z)-8-dodecenyl acetate, (Z)-11-tetradecenyl acetate, (Z)-13-eicosen-10-one, 14-methyl-1-octadecene, and the like, pheromones.

[0122] The imidazole compound of the present application or a salt thereof has an action of killing adult insects, killing nymphs, killing larvae, and killing eggs, and the like, and thus can be used for the control of harmful organisms such as pests attached to crops, mites, sanitary pests, stored grain pests, clothing pests, house pests, and the like.

[0123] As representative examples thereof, the following examples can be given:

[0124] Lepidoptera pests such as Spodoptera litura, Mamestra brassicae, Agrotis ipsilon, green caterpillars, Autographa nigrisigna, Plutella xylostella, Adoxophyes honmai, Homona magnanima, Carposina sasakii, Grapholita molesta, Phyllocnistis citrella, Caloptilia theivora, Phyllonorycter ringoniella, Lymantria dispar, Euproctis pseudoconspersa, Chilo suppressalis, Cnaphalocrocis medinalis, Ostrinia nubilalis, European corn borer, Hyphantria cunea, Cadra cautella, Heliothis spp., Helicoverpa spp., Agrotis spp., Tinea translucens, Cydia pomonella, Pectinophora gossypiella, and the like;Hemiptera pests such as Myzus persicae, Aphis gossypii, Lipaphis erysimi, Rhopalosiphum padi, Riptortus clavatus, Nezara antennata, Unaspis yanonensis, Pseudococcus comstocki, Trialeurodes vaporariorum, Bemisia tabaci, Bemisia argentifolii, Psylla pyrisuga, Stephanitis nashi, Nilaparuata lugens, Laodelphax stratella, Sogatella furcifera, Nephotettix cincticeps, etc.; Coleoptera pests such as Phyllotreta striolata, Aulacophora femoralis, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, sitophilus zeamais, Callosobruchus chinensis, Popillia japonica, Anomala rufocuprea, Diabrotica, Lasioderma serricorne, lyctus brunneus, Monochamus alternatus, Anoplophora malasiaca, Agriotes, Epilachna vigintioctopunctata, Tenebroides mauritanicus, Anthonomus grandis, etc.;Dipteran pests such as housefly (Musca domestica), blowfly (Calliphora lata), Boettcherisca peregrina, Zeugodacus cucurbitae, Bactrocera dorsalis, Delia platura, Agromyza oryzae, Drosophila melanogaster, Stomoxys calcitrans, Culex tritaeniorhynchus, Aedes aegypti, Anopheles sinensis, and the like; Thysanopteran pests such as Thrips palmi Karny, Yellow tea thrips, and the like; Hymenopteran pests such as Monomorium pharaonis, Vespa simillima xanthoptera, Athalia rosae ruficornis, and the like; Orthopteran pests such as Locusta migratoria, Blattella germanica, Periplaneta americana, Periplaneta fuliginosa, and the like; Isoptera pests such as Coptotermes formosanus, Reticulitermes speratus, and the like; Siphonapteran pests such as Pulex irritans, Ctenocephalides felis felis, and the like; Anoplurans pests such as Pediculus humanus, and the like; plant parasitic nematodes such as Meloidogyne incognita, Pratylenchus, Heterodera glycines, Aphelenchoides besseyi, Bursaphelenchus xylophilus, and the like, but are not limited thereto.

[0125] The imidazole compound or salt thereof of the present application is particularly excellent in the control effect on mites, and thus can be used as an effective ingredient of a miticide. As the mites to be controlled, there can be mentioned mites belonging to the family Tetranychidae: Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Bryobia praetiosa, Bryobia rubrioculus, Dolichotetranychus floridanus, Eotetranychus boreus, Eotetranychus geniculatus, Eotetranychus pruni, Eotetranychus sexmanaculatus, Eotetranychus smithi, Eotetranychus uncatus, Oligonychus hondoensis, Oligonychus ilicis, Oligonychus karamatus, Oligonychus shinkajii, Panonychus citri, Panonychus mori, Panonychus ulmi, Tenuipalpus zhizhilashviliae, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus urticae, Tetranychus viennensis, Tuckerella pavoniformis, and the like.Mites belonging to the family Eriophyidae: Acaphylla theavagrans, Aceria paradianthi, Aceria tulipae, Aculops lycopersici, Aculops pelekassi, Aculus fockeui, Aculus schlechtendali, Calacarus carinatus, Calepitrimerus vitis, Colomerus vitis, Epitrimerus pyri, Eriophes kuko, Eriophyes chibaensis, and the like; Mites belonging to the family Astigmata: Acarus siro, Aleuroglyphus ovatus, Carpoglyphus lactis, Lardoglyphus konoi, Rhizoglyphus echinopus, Rhizoglyphus robini, Tyrophagus putrescentiae, Tyrophagus similis, and the like; Mites belonging to the family Tarsonemidae: Phytonemus pallidus, Polyphagotarsonemus latus, Tarsonemus bilobatus, Tarsonemus waitei, and the like; Mites belonging to the family Eupodidae: Penthaleus erythrocephalus, Penthaleus major, and the like;Mites belonging to the family Ixodidae (Ixodidae): Haemaphyxalis longicornis, Haemaphysalis japonica, Boophilus microplus, Dermacentor reticulatus, Dermacentor taiwanensis, Haemaphysalis flava, Ixodes ovatus, Ixodes persulcatus, Dermacentor reticulatus, and the like. In addition, there are also drug-resistant mites having resistance to conventionally known miticides.

[0126] The useful plants to which the agricultural and horticultural insecticide and acaricide of the present application can be applied are not particularly limited, and examples thereof include cereals (e.g., rice, barley, wheat, rye, oat, corn, and the like), legumes (soybean, azuki bean, broad bean, pea, kidney bean, peanut, and the like), fruit trees or fruit plants (apple, citrus, pear, grape, peach, plum, cherry, walnut, chestnut, almond, banana, and the like), leaf or fruit vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, onion (green onion, winter onion), sweet pepper, eggplant, strawberry, pepper, okra, leek, and the like), root or stem vegetables (carrot, potato, sweet potato, taro, radish, turnip, lotus root, burdock, garlic, Chinese onion, and the like), processed crops (cotton, hemp, sugar beet root, hops, sugarcane, sugar beet, olive, rubber, coffee, tobacco, tea, and the like), melons (pumpkin, cucumber, watermelon, true gourd, melon, and the like), pasture grasses (orchard grass, sorghum, timothy, clover, alfalfa, and the like), turf grasses (Korean bentgrass, Agrostis, and the like), ornamental crops such as spices (lavender, rosemary, thyme, parsley, pepper, ginger, and the like), flowers (chrysanthemum, rose, carnation, orchid, tulip, lily, and the like), garden trees (ginkgo, cherry, coral tree, and the like), forest trees (fir, fish-scale spruce, pine, cypress, Japanese cypress, eucalyptus, and the like), and the like.

[0127] The "plant" according to the present application also includes plants which have been rendered resistant by classical methods of breeding or by genetic recombination techniques to herbicides including HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr, thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthetase inhibitors such as phosphinothricin, acetyl-CoA carboxylase inhibitors such as alloxydim, bromoxynil, dicamba, 2,4-D, and the like.

[0128] As examples of "plants" to which resistance is conferred by classical breeding methods, there are rapeseed, wheat, sunflower, rice, which are resistant to imidazolinone ALS inhibitor herbicides such as imazethapyr, and have been sold under the trade name of Clearfield (registered trademark). There is soybean, which is resistant to sulfonylurea ALS inhibitor herbicides such as thifensulfuron-methyl, and has been sold under the trade name of STS soybean, which is also obtained by classical breeding methods. As examples of plants to which resistance to acetyl-CoA carboxylase inhibitors such as trion oxime, aryloxyphenoxypropionic acid herbicides, etc. is conferred by classical breeding methods, there are SR corn (Cone), etc.

[0129] Further, plants to which resistance to acetyl-CoA carboxylase inhibitors is conferred are described in Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA) Vol. 87, pp. 7175-7179 (1990), etc. Further, a variant acetyl-CoA carboxylase having resistance to acetyl-CoA carboxylase inhibitors has been reported in Weed Science Vol. 53, pp. 728-746 (2005), etc., and plants having resistance to acetyl-CoA carboxylase inhibitors can be obtained by introducing such a variant acetyl-CoA carboxylase gene into plants by genetic recombination techniques, or by introducing a variant related to the conferring of resistance into plant acetyl-CoA carboxylases, and plants having resistance to acetyl-CoA carboxylase inhibitors, ALS inhibitors, etc. can also be obtained by techniques such as chimeraplasty technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285:316-318.), in which a nucleic acid having a base substitution variant is introduced into plant cells to introduce an amino acid substitution variant site-specifically into acetyl-CoA carboxylase genes, ALS genes, etc. of plants, and these plants can also use the insecticide and acaricide for agricultural and horticultural use of the present application.

[0130] For the control of various pests, the agricultural and horticultural insecticide and acaricide of the present application is directly applied or diluted with water or the like or applied in a suspended form in an effective amount for the control of the pests or nematodes to plants in which the pests and nematodes are expected to occur, for example, to fruit trees, cereals, vegetables, etc. in which the pests and nematodes occur, and in addition to the application to the stems and leaves, the agricultural and horticultural insecticide and acaricide of the present application can be used by seed treatment such as seed dipping, seed coating, calcium superoxide treatment, soil treatment such as soil mixing, strip application, bed soil mixing, plug treatment, planting hole treatment, root treatment, top dressing, rice box treatment, water surface application, etc. to be absorbed by the roots. In addition, it can be used by application to a nutrient solution in hydroponics, fumigation, injection into a trunk, etc.

[0131] In addition, the agricultural and horticultural insecticide and acaricide of the present application is directly applied or diluted with water or the like or applied in a suspended form in an effective amount for the control of the pests to a place in which the pests are expected to occur, for example, in addition to the application to stored grain pests, house pests, sanitary pests, forest pests, etc., it can be used as a coating for house building materials, fumigation, baits, etc.

[0132] As the method of seed treatment, for example, there can be mentioned a method in which a liquid or solid preparation is dipped in a diluted or undiluted liquid state to allow the agent to permeate, a method in which a solid preparation or a liquid preparation is mixed with seeds and subjected to a coating treatment to adhere to the surface of the seeds, a method in which seeds are coated by mixing with an adhering carrier such as a resin or a polymer, a method in which seeds are applied in the vicinity of the seeds at the time of planting, etc.

[0133] The "seeds" to which the seed treatment is applied are plant bodies used in the propagation of plants at the initial stage of cultivation, and in addition to seeds, for example, there can be mentioned bulbs, tubers, seed potatoes, plant buds, bulbs, corms or cuttage plant bodies for the vegetative propagation.

[0134] As the method of application to the stems and leaves of crops or pests such as stored grain pests, house pests, sanitary pests or forest pests, for example, there can be mentioned a method in which a liquid preparation such as an emulsion or a suspension or a solid preparation such as a wettable powder or a granular wettable powder is diluted with water as appropriate and applied, a method in which a powder is applied, fumigation, etc.

[0135] As the method of application to the soil, for example, there can be mentioned a method in which a liquid preparation is diluted with water or applied undiluted to the roots of plant bodies or a seedbed for raising seedlings, a method in which a granule is applied to the roots of plant bodies or a seedbed for raising seedlings, a method in which a powder, a wettable powder, a granular wettable powder, a granule, etc. are applied to the entire soil before sowing or before transplanting plant bodies, a method in which a powder, a wettable powder, a granular wettable powder, a granule, etc. are applied to a planting hole, a strip, etc. before sowing or before planting plant bodies, etc.

[0136] As a method of applying the rice to a seedling box, the dosage form can be different depending on the application timing such as at the time of sowing, during the greening period, at the time of transplanting, and the like, and can be applied in the form of a powder, a granular wettable powder, a granule, or the like. It can be applied by mixing with the cultivation soil, and mixing of the cultivation soil and a powder, a granular wettable powder, or a granule, or the like can be performed, for example, bed soil mixing, soil covering mixing, mixing with the entire cultivation soil, or the like. It can be simply applied by alternately forming layers of the cultivation soil and various formulations.

[0137] As a method of applying to a paddy field, a solid formulation such as a jumbo, a package, a granule, a granular wettable powder, or the like, a liquid formulation such as a flowable, an emulsion, or the like, is generally scattered on a paddy field in a water-flooded state. In addition, at the time of transplanting, an appropriate formulation can be scattered and injected into the soil directly or after mixing with a fertilizer. In addition, it can be applied labor-savingly by using a liquid medicine such as an emulsion, a flowable, or the like, at a water inflow source in a paddy field such as a water inlet, an irrigation device, or the like, along with the supply of water.

[0138] In upland crops, treatment can be performed on the cultivation carrier or the like in the vicinity of the seed or the plant body during sowing to seedling. In plants that are directly sown in an upland field, in addition to direct treatment of the seed, treatment of the roots of the plant in cultivation is preferred. Spreading treatment using a granule or irrigation treatment in a liquid state using a liquid or non-diluted agent is possible. Sowing after mixing a granule with the cultivation carrier before sowing is also a preferred treatment.

[0139] As a treatment during sowing and seedling of a cultivation plant that is transplanted, in addition to direct treatment of the seed, irrigation treatment using a liquid agent or spreading treatment using a granule is preferred. In addition, treatment of a planting hole using a granule at the time of planting or mixing of a granule with a cultivation carrier in the vicinity of the transplanting position is also a preferred treatment.

[0140] In this specification, if there is any discrepancy between the chemical name and the chemical structure, the structure is preferred. Generally, the compounds of the present application can be prepared by the methods described in the present application, unless otherwise specified. The starting materials, reagents, and the like used for the preparation of the compounds of the present application are commercially available or can be prepared by conventional methods in the art.

[0141] EA represents ethyl acetate; PE represents petroleum ether; DCM represents dichloromethane; THF represents tetrahydrofuran.

[0142] I. Preparation Examples

[0143] Example 1

[0144] This example is the preparation of 2-(2-fluoro-4-methyl-5-((2,2,2- trifluoroethyl)thio)phenyl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (Compound 1)

[0145] The specific preparation process is as follows:

[0146] (1) A reaction bottle was sequentially added with HC1 (30%, 45 mL), 1-1 (55 mmol), and an aqueous NaNC solution was slowly added dropwise at 0-5 °C, and stirring was continued for 1 h; KSCN (82 mmol), CuSCN (5.5 mmol), K2CO3 (55 mmol), and acetonitrile (100 mL) were added to another reaction bottle, and the above reaction solution was slowly added dropwise at 0-5 °C, and reaction was continued for 2 h; after the reaction was completed, water was added, and EA extraction was performed, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain compound 1-2 as a brown solid.

[0147] (2) A reaction bottle was sequentially added with compound 1-2 (44 mmol), DMF (100 mL), 2-iodo-1,1,1-trifluoroethane (89 mmol), K2CO3 (133 mmol), and hydroxymethanesulfinate monosodium salt (22 mmol), and reaction was performed overnight at 60 °C; water was added, and EA extraction was performed, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and column chromatography (EA / PE = 10%) was performed to separate and purify to obtain compound 1-3 as a light yellow liquid.

[0148] (3) A reaction bottle was sequentially added with compound 1-3 (18 mmol), THF (50 mL), H2O (10 mL), and NaOH (35 mmol), and stirring was performed at room temperature for 2 h; water was added, and the pH was adjusted to 5-6, and the mixture was spin-dried; the crude product was dissolved in DCM (dichloromethane), filtered, and the filtrate was concentrated under reduced pressure to obtain compound 1-4 as a white solid.

[0149] (4) A reaction bottle was sequentially added with compound 1-4 (11 mmol), THF (30 mL), 5-trifluoromethyl-3-amino-2-methylamino pyridine (11 mmol), Et3N (34 mmol), and HATU (13 mmol), and stirring was performed at room temperature overnight; water was added, and EA extraction was performed, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and column chromatography was performed with an eluent of ethyl acetate / petroleum ether = 2 / 5 (EA / PE = 40%) to separate and purify to obtain compound 1-5 as a brown liquid.

[0150] (5) Into the reaction flask was added compound 1-5 (6.8 mmol), acetic acid (30 mL) successively, heated to reflux and stirred for 2 h, the solvent was removed, the pH was adjusted to be alkaline, extracted with ethyl acetate (EA), the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and separated and purified by column chromatography (EA / PE = 5%) to obtain compound 1 as a white solid. 1 H NMR (400 MHz, DMSO-d6) δ 8.87-8.82 (m, 1H), 8.62 (d, J = 1.5 Hz, 1H), 7.96 (d, J = 7.0 Hz, 1H), 7.52 (d, J = 11.0 Hz, 1H), 4.02 (q, J = 10.3 Hz, 2H), 3.80 (d, J = 1.4 Hz, 3H), 2.52 (s, 3H).

[0151] Example 2

[0152] This example is the preparation of 2-(2-fluoro-4-methyl-5-((2,2,2- trifluoroethyl)sulfinyl)phenyl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (compound 2)

[0153] The specific preparation process is as follows:

[0154] (1) Into the reaction flask was added compound 1 (3.53 mmol), DCM (15 mL) successively, m-CPBA (meta-chloroperoxybenzoic acid) (3.53 mmol) was added in batches at 0 °C, and stirred at room temperature for 2 h, water was added, extracted with DCM, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and separated and purified by column chromatography (EA / PE = 40%) to obtain the title compound 2 as a white solid. 1 H NMR (400 MHz, DMSO-d6) δ 8.85 (d, J = 1.4 Hz, 1H), 8.63 (d, J = 1.8 Hz, 1H), 8.23 (d, J = 7.1 Hz, 1H), 7.63 (d, J = 11.0 Hz, 1H), 4.30 (dq, J = 14.7, 10.9 Hz, 1H), 4.13 (dq, J = 14.8, 10.8 Hz, 1H), 3.83 (d, J = 1.8 Hz, 3H), 2.52 (d, J = 2.8 Hz, 3H).

[0155] Example 3

[0156] This example is the preparation of 2-(2-fluoro-4-methyl-5-((2,2,2- trifluoroethyl)sulfinyl)phenyl)-1-methyl-5-(trifluoromethyl)-1H-benzo[d]imidazole (compound 3)

[0157] The specific preparation process is as follows:

[0158] (1) A reaction bottle was sequentially added with compound 1-4 (7.46 mmol), THF (30 mL), [2-amino-4-(trifluoromethyl)phenyl]-methyl-amine (7.46 mmol), Et3N (22.37 mmol), HATU (8.95 mmol), stirred at room temperature overnight, added with water, extracted with EA, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and separated and purified by column chromatography (EA / PE = 40%) to obtain compound 3-1 as a brown liquid.

[0159] (2) A reaction bottle was sequentially added with compound 3-1 (6.8 mmol), acetic acid (30 mL), heated and stirred at reflux for 2 h, the solvent was removed by rotary evaporation, the pH was adjusted to be alkaline, extracted with EA, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and separated and purified by column chromatography (EA / PE = 5%) to obtain compound 3 as a white solid. 1 H NMR (400 MHz, DMSO-d6) δ 8.10 (dd, J = 1.8, 0.9 Hz, 1H), 7.90 (dd, J = 7.8, 6.0 Hz, 2H), 7.67 (dd, J = 8.7, 1.7 Hz, 1H), 7.52-7.44 (m, 1H), 4.01 (q, J = 10.4 Hz, 2H), 3.77 (d, J = 1.5 Hz, 3H), 2.51 (s, 3H).

[0160] Example 4

[0161] This example is the preparation of 2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-1-methyl-1H-benzo[d]imidazole (compound 4)

[0162] The specific preparation process is as follows:

[0163] (1) A reaction bottle was sequentially added with compound 1-4 (11 mmol), THF (30 mL), N-methyl-1,2-phenylenediamine (11 mmol), Et3N (34 mmol), HATU (13 mmol), stirred at room temperature overnight, added with water, extracted with EA, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and separated and purified by column chromatography with eluent ethyl acetate / petroleum ether = 2 / 5 (EA / PE = 40%) to obtain compound 4-1 as a brown liquid.

[0164] (2) The reaction bottle was added with compound 4-1 (8.06 mmol) and acetic acid (30 mL) in sequence, and stirred at reflux for 2 h. The solvent was removed, the pH was adjusted to be alkaline, and EA extraction was performed. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and separated and purified by column chromatography (EA / PE=5%) to obtain compound 4 as a white solid. 1 HNMR (400 MHz, DMSO-d6) δ 7.87 (d, J = 7.1 Hz, 1H), 7.71 (dd, J = 7.5, 1.1 Hz, 1H), 7.64 (dd, J = 7.7, 1.2 Hz, 1H), 7.46 (d, J = 10.8 Hz, 1H), 7.31-7.30 (m, 2H), 4.01 (q, J = 10.4 Hz, 2H), 3.71 (d, J = 1.7 Hz, 3H), 2.50 (s, 3H).

[0165] The compounds in Table 2 were prepared according to the above preparation method

[0166] Biological test:

[0167] The test is to test the acaricidal activity of the compounds prepared in the application, specifically the acaricidal activity of the compounds on Tetranychus cinnabarinus and Tetranychus urticae adults and the acaricidal activity determination of different concentrations of the compounds.

[0168] 1. The compound of the application is prepared in a small amount of DMF as a solvent and 0.5% TW80 as an emulsifier to obtain a 1% concentration of the pesticide, which is used according to the experimental requirements and diluted to the required concentration for the test.

[0169] 2. The specific test process is as follows: select peanut leaves of similar size, and attach 20-30 adult mites of similar size to each leaf, and place one leaf in each treatment; immerse the leaf with mites in the prepared pesticide for 5 s, and use a water-absorbing paper to absorb the pesticide around the leaf and mites. Place 2 layers of filter paper in a petri dish, add water to moisten, and then place the above leaves on the filter paper in a constant temperature (27°C) incubator with a light-dark ratio of 14:10. After 48 h, investigate the number of live mites and calculate the mortality rate.

[0170] The compounds of this invention were diluted to five concentration gradients of 50 ppm, 25 ppm, 12.5 ppm, 6.25 ppm, and 3.125 ppm, respectively, and tested according to the above procedure. The specific results are shown in Table 3. The test results show that compounds 1, 2, and 3 achieved a 100% mortality rate at concentrations of 12.5 ppm and above, demonstrating excellent acaricidal effects. The test results against the two-spotted spider mite using the same method are shown in Table 4. The results show that compounds 1, 2, and 3 achieved a mortality rate of over 100% against the two-spotted spider mite at concentrations of 12.5 ppm and above, demonstrating good acaricidal effects.

[0171] Table 3 Results of the test for Tetranychus cinnabarinus

[0172] Table 4. Results of the two-spotted spider mite test.

[0173] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

A compound of formula I, a stereoisomer, nitroxide or salt thereof, wherein D, E, F, G are independently selected from N or CR2, Q is NR1, O or S; X1, X2, X3, X4are independently selected from the group consisting of H, halogen, CN, NO2, C1-C 10 alkyl and halogen C1-C 10 alkyl; one of X1, X2, X3, X4is selected from the group consisting of H, halogen, CN, NO2, C1-C Y is selected from S, S=O, O=S=O or R3-N=S=O; R1is selected from H, CN, optionally substituted C1-C 10 alkyl, optionally substituted C3-C 10 cycloalkyl, optionally substituted C1-C 10 alkoxy, halogenated C3-C 10 cycloalkoxy, optionally substituted C2-C 10 alkenyl, optionally substituted C2-C 10 alkynyl, optionally substituted C1-C 10 alkylcarbonyl, optionally substituted C1-C 10 alkoxycarbonyl, optionally substituted arylcarbonyl, optionally substituted aryloxycarbonyl; R2is selected from the group consisting of H, halogen, CN, NO2, C1-C 10 alkyl and halogen C1-C 10 alkyl; R3is selected from H, CrC 10 alkyl and halo CrC 10 alkyl. The compound of formula I according to claim 1, a stereoisomer, nitroxide or salt thereof, characterized in that D is N or CR2. Compound of formula I according to claim 1 or 2, a stereoisomer, nitroxide or salt thereof, characterized in that X1, X2, X3, X4are independently selected from one of H, halogen, and halogenated C1-C6alkyl. The compound of formula I according to claim 1, a stereoisomer, nitroxide or salt thereof, characterized in that Y is S, S=O or O=S=O. The compound of formula I, its stereoisomers, nitroxide or salts thereof according to claim 3, characterized in that R1is selected from one of H, halogen, C1-C6alkyl and halogenated C1-C6alkyl. The compound of claim 4, isomers thereof, or salts thereof, characterized in that, R2is selected from one of H, halogen, C1-C6alkyl and halogenated C1-C6alkyl. The compound of formula I, its stereoisomers, nitroxides or salts thereof according to claim 1, characterized in that The compounds are selected from the following compounds: The compound of formula I, its stereoisomers, nitroxides or salts thereof according to any one of claims 1 to 7, characterized in that The compounds are selected from the following compounds: A pesticide composition characterized in that, A compound of the formula I according to any one of claims 1 to 7, a stereoisomer, a nitroxide or a salt thereof, as active ingredient.

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