Pyridyl-substituted imidazole ring compound and preparation method therefor, insecticidal composition, and use

Abstract

Provided are a pyridyl-substituted imidazole ring compound, a composition comprising same, and a use, relating to the technical field of pesticides. The compound is as shown in general formula I: [Formula I], wherein Q1 and Q2 each independently represent CH, C-halogen or N; X represents haloalkoxy; Y represents alkyl; R1 represents hydrogen, halogen, alkyl, alkenyl, etc.; and R2 represents hydrogen, alkyl, alkenyl, alkynyl, etc. The compound exhibits an excellent control effect on Spodoptera frugiperda, armyworms, etc.

Description

A pyridyl-substituted imidazole cyclic compound, its preparation method, insecticidal composition and application Technical Field

[0001] This invention belongs to the field of pesticide technology, specifically relating to a pyridyl-substituted imidazole cyclic compound, its preparation method, insecticidal composition, and application. Background Technology

[0002] In recent years, due to the long-term use of pest control agents, such as insecticides or fungicides, pests have acquired resistance, becoming difficult to control with existing pesticides or fungicides. Furthermore, some known pest control agents are highly toxic, or some damage ecosystems through their long-term persistence. Therefore, despite the large number of known pesticides, there is a need to develop new pest control agents with low toxicity and low residue. Summary of the Invention

[0003] This invention provides a pyridyl-substituted imidazole ring compound, its preparation method, insecticidal composition, and application. The compound exhibits excellent insecticidal activity against fall armyworm, armyworm, and other pests.

[0004] The technical solution adopted in this invention is as follows:

[0005] A pyridyl-substituted zimidazole ring compound, as shown in general formula I:

[0006] Where Q1 and Q2 independently represent CH, C-halogen or N, respectively;

[0007] X represents a haloalkoxy group;

[0008] Y represents alkyl;

[0009] R1 represents hydrogen, halogen, alkyl, alkenyl, ynyl, -OR9, -S(O). m R9 or The alkyl, alkenyl, or alkynyl group is optionally substituted with at least one group selected from halogens or -OR9;

[0010] R2 represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl or -alkylene-OR9;

[0011] R8 represents hydrogen, alkyl, or haloalkyl;

[0012] R9 can independently represent hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, or cycloalkylalkyl;

[0013] m represents 0, 1, or 2;

[0014] The aforementioned "cycloalkyl", "heterocyclic" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, -OR 10 -SR 10 -(CO)R 10 -(CO)OR 10 -(SO)R 10 or -(SO2)R 10 At least one group in it is replaced;

[0015] R 10 Each of these groups independently represents hydrogen, alkyl, haloalkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy.

[0016] Preferably, X represents a halogenated C1-C8 alkoxy group;

[0017] Y represents C1-C8 alkyl;

[0018] R1 represents hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, -OR9, -S(O). m R9 or The C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl group is optionally substituted with at least one group selected from halogen or -OR9;

[0019] R2 represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, or -(C1-C8 alkylene)-OR9;

[0020] R8 represents hydrogen, C1-C8 alkyl, or halo-C1-C8 alkyl;

[0021] R9 can independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl or C3-C8 cycloalkyl-C1-C8 alkyl.

[0022] The aforementioned “C3-C8 cycloalkyl,” “heterocyclic,” or “aryl” is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, -OR 10 -SR 10 -(CO)R 10 -(CO)OR10 -(SO)R 10 or -(SO2)R 10 At least one group in it is replaced;

[0023] R 10 Each of these groups independently represents hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy, or halo-C1-C8 alkoxy.

[0024] More preferably, X represents a halogenated C1-C6 alkoxy group;

[0025] Y represents C1-C6 alkyl;

[0026] R1 represents hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, -OR9, -S(O). m R9 or The C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl groups are optionally substituted with at least one group selected from halogens or -OR9;

[0027] R2 represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, or -(C1-C6 alkylene)-OR9;

[0028] R8 represents hydrogen, C1-C6 alkyl, or halo-C1-C6 alkyl;

[0029] R9 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl or C3-C6 cycloalkyl-C1-C6 alkyl.

[0030] The aforementioned “C3-C6 cycloalkyl,” “heterocyclic,” or “aryl” is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 ynyl, -OR 10 -SR 10 -(CO)R 10 -(CO)OR 10 -(SO)R 10 or -(SO2)R 10 At least one group in it is replaced;

[0031] R 10 Each of these groups independently represents hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy, or halo-C1-C6 alkoxy.

[0032] In one specific embodiment, R1 represents a halogenated C1-C6 alkyl group.

[0033] In the definitions of compounds shown in the above general formulas and in all the following structural formulas, the technical terms used, whether alone or in compound terms, represent the following substituents: alkyl groups having more than two carbon atoms can be straight-chain or branched. For example, in the compound term "-alkylene-OR9", alkylene can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. Alkyl groups are, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such as n-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl, tert-butyl, or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, alkenyl groups are, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl. Alkynyl groups are, for example, ethynyl, propynyl, but-2-yn-1-yl, but-3-yn-1-yl, and 1-methylbut-3-yn-1-yl. Multiple bonds can be in any position in each unsaturated group. Cycloalkyl groups are carbocyclic saturated ring systems having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, cycloalkenyl groups are monocyclic alkenyl groups having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, wherein double bonds can be in any position. Halogens are fluorine, chlorine, bromine, or iodine.

[0034] Unless otherwise specified, the term "aryl" in this invention includes, but is not limited to, phenyl, naphthyl, and... The "heterocyclic group" includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups. And, including but not limited to, heteroaryl groups, i.e., aromatic cyclic groups containing, for example, 3 to 6 ring atoms and optionally fused with benzo[a] rings, wherein 1 to 4 (e.g., 1, 2, 3, or 4) heteroatoms are selected from oxygen, nitrogen, and sulfur, for example

[0035] The terms "optional" or "optionally" mean that the event or situation described below may or may not occur, and the description includes instances where said event or situation occurs and instances where said event or situation does not occur. For example, the term "optionally...substituted" means that the specified atom or group is unsubstituted or substituted by one or more substituents. If a group is substituted by a group, this should be understood to mean that the group is substituted by one or more groups, either the same or different, selected from those groups mentioned. Furthermore, the same or different substitution characters contained in the same or different substituents are chosen independently and may be the same or different. This also applies to ring systems formed from different atoms and units. Meanwhile, the scope of the claims excludes compounds that are chemically unstable under standard conditions, as known to those skilled in the art.

[0036] Furthermore, unless otherwise specified, the phrase "replaced by at least one group" in this invention refers to being replaced by, for example, 1, 2, 3, 4, or 5 groups; groups without specific attachment positions (including heterocyclic groups, aryl groups, etc.) can be attached at any position, including positions attached to C or N; if it is substituted, the substituent can also be substituted at any position, as long as it conforms to the rules of chemical bond attachment. For example, a heteroaryl group substituted by one methyl group. Can represent wait.

[0037] If various functional groups are present, the present invention also includes any ketone and enol tautomer forms, mixtures thereof, and salts thereof.

[0038] The method for preparing the pyridyl-substituted zimidazole ring compound includes the following steps:

[0039] The compounds represented by general formulas II and III were coupled to prepare the compound represented by general formula I, and the reaction equation is as follows:

[0040] The definitions of Q1, Q2, X, Y, R1, and R2 are as shown above. Either M1 or M2 is a halogen, and the other is... Or -B(OH)2.

[0041] In one specific embodiment, the reaction is carried out in the presence of a base, a solvent, and a catalyst.

[0042] In one specific embodiment, the base is selected from at least one of inorganic bases (such as NaH, KH, NaOH, KOH, K2CO3, Na2CO3, Cs2CO3, KF, CsF, etc.) or organic bases (such as pyrazole, triethylamine, N,N-diisopropylethylamine, pyridine, DIEA, potassium trimethylsilanol, AcOK, AcONa, MeONa, EtONa, t-BuONa, t-BuOK, etc.).

[0043] In one specific embodiment, the solvent is an organic solvent / water, wherein the organic solvent is selected from at least one of aromatic hydrocarbons (such as benzene, chlorobenzene or toluene), DMF, DMA, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane or ethyl acetate.

[0044] In one specific embodiment, the catalyst is selected from at least one of Pd(PPh3)4, Pd(dppf)Cl2, Pd(dppf)Cl2.CH2Cl2, Pd(OAc)2, PdCl2(PPh3)2 or 1,1'-bis(diphenylphosphine)ferrocene palladium(II) dichloromethane complex.

[0045] Or either M1 or M2 is an alkylthio group, and the other is... Or -B(OH)2;

[0046] Preferably, the reaction is carried out in the presence of a solvent and a catalyst; more preferably, the solvent is selected from at least one of aromatic hydrocarbons (such as benzene, chlorobenzene or toluene), dichloroethane, dioxane or dichloromethane; the catalyst is a palladium reagent and / or a copper reagent, wherein the palladium reagent is selected from at least one of Pd(PPh3)4, Pd(dppf)Cl2, Pd(dppf)Cl2.CH2Cl2, Pd(OAc)2, PdCl2(PPh3)2 or 1,1'-bis(diphenylphosphine)ferrocene palladium(II) dichloromethane complex, and the copper reagent is copper(I)thiophene-2-carboxylic acid.

[0047] In addition, compounds represented by general formula I can be prepared by referring to the methods shown in CN201780006638.8, CN202280017806.4, etc.

[0048] The present invention also provides an intermediate, as shown in general formula II.

[0049] Salts of the compounds suitable for use according to the present invention, such as salts of bases or salts of acid addition, are conventional, non-toxic salts, preferably agriculturally and / or physiologically acceptable salts. Salts with inorganic bases are preferred, such as alkali metal salts (e.g., sodium, potassium, or cesium salts), alkaline earth metal salts (e.g., calcium or magnesium salts), ammonium salts; or salts with organic bases, particularly organic amines, such as triethylammonium salts, dicyclohexylammonium salts, N,N'-dibenzylethylidene diammonium salts, pyridinium salts, methylpyridinium salts, or ammonium ethanolate salts; salts with inorganic acids (e.g., hydrochlorides, hydrobromates, dihydrogen sulfates, trihydrogen sulfates, or phosphates); and salts with organic carboxylic acids or organic sulfonic acids (e.g., formates, acetates, trifluoroacetates, maleates, tartrates, methanesulfonates, benzenesulfonates, or 4-toluenesulfonates). Tertiary amines, such as some compounds of the present invention, are known to form N-oxides, which are also salts of the present invention.

[0050] Depending on the nature of the substituents, compounds of Formula I can exist as geometrically and / or optically active isomers or mixtures of corresponding isomers with different compositions. These stereoisomers are, for example, enantiomers, diastereomers, transisomers, or geometric isomers. Therefore, the present invention includes pure stereoisomers and any mixtures of these isomers.

[0051] The present invention also relates to a method for controlling animal pests, wherein the compound of formula I can act on the animal pests and / or their habitats. The control of said animal pests is preferably carried out in agriculture and forestry, as well as in the protection of materials. Methods preferably excluded from this method include surgical and therapeutic treatments for humans or animals, and diagnostic methods performed on humans or animals.

[0052] The present invention also relates to the use of compounds of Formula I as insecticides, and in particular as crop protectants.

[0053] In the context of this application, the term "insecticide" often also includes the term "crop protectant".

[0054] Compounds of Formula I, exhibiting good plant tolerance, favorable homeothermic animal toxicity, and good environmental compatibility, are suitable for the following uses: protecting plants and plant organs from biotic and abiotic stresses; increasing harvest yield; improving the quality of harvested material; and controlling animal pests, especially insects, arachnids, worms, nematodes, and mollusks, encountered in agriculture, horticulture, livestock farming, aquaculture, forestry, landscaping and recreational facilities, protection of stored products and materials, and in the sanitation sector. These compounds are preferably used as insecticides. They are effective against commonly susceptible and resistant species and are resistant to all or part of the developmental stages. The aforementioned pests include, but are not limited to: pests from the phylum Arthropoda, especially from the class Arachnida; pests from the class Chilopoda; pests from the orders Collembola; pests from the class Diplopoda; pests from the class Insecta; pests from the order Coleoptera; pests from the order Diptera; pests from the order Heteroptera; pests from the order Homoptera; pests from the order Hymenoptera; and pests from the order Isopoda. a) Pests, including those from the order Isoptera, Lepidoptera, Orthoptera or Saltatoria, Phthiraptera, Psocoptera, Siphonaptera, Thysanoptera, Zygentoma (=Thysanura) (a) (a) (a) (b) (c) (c) (d ...

[0055] At certain concentrations and application rates, compounds of Formula I may also optionally be used as insecticides, safeners, growth regulators, or agents for improving plant performance; as fungicides and gametoxins, for example as fungicides, antifungals, bactericides, antivirals (including antiviral agents), or as agents against MLO (mycoplasma-like organisms) and RLO (rickettsia-like organisms). Where appropriate, they may also be used as intermediates or precursors for the synthesis of other active ingredients.

[0056] The present invention also relates to formulations comprising at least one compound of formula I and forms of use prepared therefrom as insecticides, such as impregnation, dripping, and spraying liquids. In some cases, the forms of use include other insecticides and / or adjuvants with enhancing effects, such as penetrants, for example, vegetable oils (e.g., rapeseed oil, sunflower oil), mineral oils (e.g., paraffin oil), alkyl esters of vegetable fatty acids (e.g., rapeseed oil methyl ester or soybean oil methyl ester), or alkanol alkoxylates; and / or spreaders, such as alkylsiloxanes and / or salts (e.g., organic or inorganic ammonium or phosphate salts, such as ammonium sulfate or diammonium hydrogen phosphate); and / or retention promoters, such as dioctyl sulfosuccinic acid or hydroxypropyl guar gum polymers; and / or wetting agents, such as glycerin; and / or fertilizers, such as ammonium-, potassium-, or phosphorus-containing fertilizers.

[0057] Commonly used formulations include, for example, water-soluble liquids (SL), emulsifiable concentrates (EC), emulsions (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR), and capsule concentrates (CS); these formulations and other possible formulation types are described, for example, by Crop Life International in the following literature: Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, and FAO Plant Production and Protection Papers-173 – developed by the FAO / WHO Joint Committee on Pesticide Standards, 2004, ISBN: 9251048576. In addition to one or more compounds of Formula I, the formulations may optionally contain other agrochemically active ingredients.

[0058] These are preferably formulations or forms of use comprising: adjuvants, such as fillers, solvents, spontaneous accelerators, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners; and other adjuvants, such as adjuvants. In this context, an adjuvant is a component that enhances the biological efficacy of the formulation, while the component itself does not have any biological efficacy. Examples of adjuvants are agents that promote retention, spreading, adhesion to leaf surfaces, or penetration.

[0059] These formulations are prepared in a known manner, for example by mixing a compound of formula I with an adjuvant, such as a filler, solvent, and / or solid carrier, and / or other adjuvants such as surfactants. The formulation is prepared in a suitable device or before or during application.

[0060] The adjuvant used may be a formulation suitable for imparting the compound of Formula I or a substance prepared from such formulations that has specific properties for use in a form of application (such as ready-to-use insecticides, such as spray liquids or seed dressing products), said specific properties being, for example, specific physical properties, technical properties and / or biological properties.

[0061] Suitable fillers are, for example, water, polar and nonpolar organic chemical liquids, such as those selected from: aromatic or non-aromatic hydrocarbons (e.g., paraffin, alkylbenzene, alkylnaphthalene, chlorobenzene), alcohols and polyols (which may optionally be substituted, etherified and / or esterified), ketones (e.g., acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides, lactams (e.g., N-alkylpyrrolidone) and lactones, sulfones and sulfoxides (e.g., dimethyl sulfoxide).

[0062] If the filler used is water, organic solvents may also be used as co-solvents. Useful liquid solvents include: aromatic compounds such as xylene, toluene, or alkylnaphthalene; chlorinated aromatic and aliphatic hydrocarbons such as chlorobenzene, vinyl chloride, or dichloromethane; aliphatic hydrocarbons such as cyclohexane or paraffins such as mineral oil fractions, mineral oils, and vegetable oils; alcohols such as butanol or ethylene glycol and their ethers and esters; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone; highly polar solvents such as dimethylformamide, dimethylacetamide, and dimethyl sulfoxide, as well as water.

[0063] In principle, all suitable solvents may be used. Examples of suitable solvents include aromatic hydrocarbons such as xylene, toluene, or alkylnaphthalene; chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride, and dichloromethane; aliphatic hydrocarbons such as cyclohexane, paraffin, mineral oil fractions, mineral oil, and vegetable oil; alcohols such as methanol, ethanol, isopropanol, butanol, or ethylene glycol and their ethers and esters; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone; strongly polar solvents such as dimethyl sulfoxide; and water.

[0064] In principle, all suitable carriers may be used. Useful carriers include, in particular, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, magnesia, montmorillonite, or diatomaceous earth; and ground synthetic materials such as finely ground silica, alumina, and natural or synthetic silicates, resins, waxes, and / or solid fertilizers. Mixtures of these carriers may also be used. Useful carriers for granules include, for example, crushed and graded natural rocks such as calcite, marble, pumice, sepiolite, and dolomite; and synthetic granules of inorganic and organic powders; and granules of organic materials such as sawdust, paper, coconut husks, corn cobs, and tobacco stems.

[0065] Liquefied gaseous fillers or solvents can also be used. Particularly suitable fillers or carriers are those that are gaseous at ambient temperature and atmospheric pressure, such as aerosol propellant gases, including halogenated hydrocarbons, as well as butane, propane, nitrogen, and carbon dioxide.

[0066] Examples of emulsifiers and / or foaming agents, dispersants, or wetting agents, or mixtures of these surfactants, having ionic or nonionic properties, include: salts of polyacrylic acid; salts of lignin sulfonic acid; salts of phenol sulfonic acid or naphthalene sulfonate; condensates of ethylene oxide with fatty alcohols or fatty acids or fatty amines or substituted phenols (preferably alkylphenols or arylphenols); salts of sulfosuccinates; taurine derivatives (preferably alkyl taurine esters); phosphate esters of polyethoxylated alcohols or phenols; fatty acid esters of polyols; and derivatives of compounds containing sulfates, sulfonates, and phosphates, such as alkylaryl polyethylene glycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, protein hydrolysis products, lignin sulfite waste, and methylcellulose. The presence of a surfactant is advantageous when one of the compounds of Formula I above and / or one of the inert carriers above is insoluble in water and is applied in water.

[0067] Other adjuvants that may be present in formulations and derived forms of use include colorants, such as inorganic pigments like iron oxide, titanium dioxide, and Prussian blue; and organic dyes, such as alizarin dyes, azo dyes, and metal phthalocyanine dyes; as well as nutrients and micronutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum, and zinc.

[0068] Additional components may be stabilizers that improve chemical and / or physical stability, such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers, or other reagents. Foaming agents and defoamers may also be present.

[0069] In addition, formulations and derived forms of use may contain the following substances as additional adjuvants: adhesives, such as carboxymethyl cellulose; and natural and synthetic polymers in powder, granule, or latex form, such as gum arabic, polyvinyl alcohol, and polyvinyl acetate; or natural phospholipids, such as cephalin, lecithin, and synthetic phospholipids. Other possible adjuvants include mineral oils and vegetable oils.

[0070] Optionally, other adjuvants may be present in the formulation and in forms of use derived therefrom. Examples of such additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic agents, penetrants, retention enhancers, stabilizers, chelating agents, complexing agents, wetting agents, and spreading agents. Generally, compounds of Formula I can be combined with any solid or liquid additive commonly used for formulation purposes.

[0071] Useful retention promoters include all those substances that reduce kinetic surface tension, such as dioctyl sulfosuccinate; or all those substances that increase viscoelasticity, such as hydroxypropyl guar polymer.

[0072] In the context of this invention, useful penetrants include all those substances commonly used to enhance the penetration of active agricultural chemicals into plants. Hereinafter, penetrants are defined as those that penetrate the plant epidermis by (typically aqueous) application liquids and / or by spray coatings, thereby increasing the fluidity of the active ingredient within the epidermis. Examples include: alcohol alkoxylates, such as coconut fat ethoxylate (10) or isotrigine ethoxylate (12); fatty acid esters, such as rapeseed oil methyl ester or soybean oil methyl ester; fatty amine alkoxylates, such as tallow amine ethoxylate (15); or ammonium and / or phosphate salts, such as ammonium sulfate or diammonium hydrogen phosphate.

[0073] The formulation preferably comprises 0.00000001% by weight to 98% by weight of a compound of formula I, more preferably 0.01% by weight to 95% by weight of a compound of formula I, and most preferably 0.5% by weight to 90% by weight of a compound of formula I, based on the weight of the formulation.

[0074] The content of the compound of Formula I in the application form prepared from the formulation (especially insecticide) can vary over a wide range. The concentration of the compound of Formula I in the application form is typically from 0.00000001% by weight to 95% by weight, preferably from 0.00001% by weight to 1% by weight, based on the weight of the application form. Application is carried out in a conventional manner suitable for the application form.

[0075] Compounds of Formula I can also be used in mixtures with one or more of the following substances: suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbial agents, beneficial organisms, pesticides, fertilizers, bird repellents, phytotonics, sterilizing agents, safeners, chemical pheromones, and / or plant growth regulators, thereby, for example, broadening the spectrum of action, prolonging the duration of action, increasing the rate of action, preventing rejection, or preventing the development of resistance. In addition, such active ingredient compositions can improve plant growth and / or tolerance to abiotic factors (such as high or low temperatures), drought, or tolerance to high water content or soil salinity. They may also improve flowering and fruiting performance, optimize germination capacity and root development, promote harvesting and increase yield, influence ripening, improve the quality and / or nutritional value of harvested products, prolong storage life, and / or improve the processing properties of harvested products.

[0076] Additionally, compounds of Formula I can be present in mixtures with other active ingredients or chemical pheromones such as attractants and / or bird repellents and / or plant activators and / or growth regulators and / or fertilizers. Similarly, compounds of Formula I can be used in mixtures with reagents used to improve plant performance such as growth, yield, and the quality of harvested material.

[0077] In a particular embodiment of the invention, the compound of formula I is a formulation in the form of a mixture with other components or in a form of use prepared from such formulations, preferably those described below.

[0078] If one of the compounds mentioned below can exist in multiple tautomeric forms, these forms are included even if they are not explicitly mentioned in various cases.

[0079] Insecticides / Acaricides / Nematodes

[0080] The active ingredients mentioned in this article by their “generic names” are known and described, for example, in The Pesticide Manual, 16 th ed., British Crop Protection Council 2012, or can be found on the internet (e.g., http: / / www.alanwood.net / pesticides).

[0081] (1) Acetylcholinesterase (AChE) inhibitors, such as carbamates, including alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, and furathioc. (ARB), isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, and xylylcarb; or organophosphates, such as azamethiphos and azinphos-ethyl. Azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chloropyrifos, chloropyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, didrotophos, and others. Dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl o-(methoxyaminothiophosphoryl)salicylic acid, isoxathionMalathion, mecarbam, methamidophos, methidathion, mevinphos, monocotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, and other similar pesticides. Piririmiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclofon, and vamidothion.

[0082] (2) GABA-gated chloride channel antagonists, such as cyclopentadiene organochlorines, such as chlordane and endosulfan; or phenylpyrazoles, such as ethiprole and fipronil.

[0083] (3) Sodium channel modulators / voltage-dependent sodium channel blockers, such as pyrethroids, including acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, and bioallethrin S-cyclopentenyl isomer. isomer), pyrethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomer] isomers]), deltamethrin, empenthrin[(EZ)-(1R)isomers], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin[(1R)-trans isomers], phenothrin[(1R)-trans isomers][isomer]), prallethrin, pyrethrine, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)isomers], tralomethrin, and transfluthrin; or DDT; or methoxychloride.

[0084] (4) Nicotinic acetylcholine receptor (nAChR) agonists, such as neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor.

[0085] (5) Allosteric activators of nicotinic acetylcholine receptors (nAChR), such as spinosides, such as spintoram and spinosad.

[0086] (6) Chloride channel activators, such as abamectins / milbemycins, such as abamectin, emamectin benzoate, lepimectin and milbemectin.

[0087] (7) Juvenile hormone mimics, such as hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

[0088] (8) Active ingredients with unknown or non-specific mechanisms of action, such as

[0089] Alkyl halides, such as methyl bromide and other alkyl halides; or chloropicrine or thiocyanate or borax or tartar emetic.

[0090] (9) Selective antifeedants, such as pymetrozine or flonicamid.

[0091] (10) Mite growth inhibitors, such as tetradifon, thiamethoxam and diflovidazin or etoxazole.

[0092] (11) Microbial disruptors of insect intestinal membranes, such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1.

[0093] (12) Inhibitors of oxidative phosphorylation, ATP interfering agents, such as butyl ether urea or organotin compounds, such as triazole tin, tricyclic tin and fenbutatin oxide or propargite or tetradifon.

[0094] (13) Oxidative phosphorylation decoupling agents that interrupt the H proton gradient, such as chlorfenapyr, dinitrocresol (DNOC) and sulfluramid.

[0095] (14) Nicotinic acetylcholine receptor antagonists, such as bensultap, cartap hydrochloride, thiocyclam and thiosultap-sodium.

[0096] (15) Type O chitin biosynthesis inhibitors, such as bistrifluron, chlofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron.

[0097] (16) Type I chitin biosynthesis inhibitors, such as buprofezin.

[0098] (17) Ecchymosis inhibitors (especially for Diptera, i.e., Diptera), such as cyromazine.

[0099] (18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0100] (19) Octopus aminergic agonists, such as amitraz.

[0101] (20) Complex-III electron transport inhibitors, such as hydramethylnone, acequinocyl, or fluacrypyrim.

[0102] (21) Complex-type I electron transport inhibitors, such as those selected from METI acaricides, such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad; or rotenone (Rotenone).

[0103] (22) Voltage-gated sodium channel blockers, such as indoxacarb or metaflumizone.

[0104] (23) Inhibitors of acetyl-CoA carboxylase, such as tetronic acid and tetramic acid derivatives, such as spirodiclofen, spiromesifen and spirotetramat.

[0105] (24) Complex-IV electron transport inhibitors, such as phosphine, such as aluminum phosphide, calcium phosphide, phosphine hydrogen and zinc phosphide; or cyanide.

[0106] (25) Complex-type II electron transport inhibitors, such as cyenopyrafen and cyflumetofen.

[0107] (28) Lanni base receptor effectors, such as diamides, such as chlorantraniliprole, cyantraniliprole and flubendiamide;

[0108] Other active ingredients include afidopyropen, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite, dicofol, diflovidazin, fluensulphone, fometoquin, flufenerim, flufenoxystrobin, and flufeniprin. role), fluopyram, flupyradifurone, fufenozide, heptafluthrin, imidaclothiz, iprodione, meperfluthrin, paichongding, pyflubumide, pyrifluquinazon, pyriminostrobin, tetramethylfluthrin, and iodomethane; and based on Bacillus thuringiensis. The reagents of firmus, I-1582, BioNeem, Votivo, and the following compounds: 3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (known from WO2005 / 077934) and 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO2006 / 043635), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl] -5-Fluorospiro[indol-3,4'-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl) methyl ketone (known from WO2003 / 106457), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006 / 003494), 3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4,5]dec-3-en-2-one (known from WO2009 / 049851), 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-Dazaspiro[4.5]dec-3-en-4-yl ethyl carbonate (known from WO2009 / 049851), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO2004 / 099160), 4-(but-2-yn-1-yloxy)-6-(3-chlorophenyl)pyrimidine (known from WO2003 / 076415), PF1364 (CAS Registry No. 1204776-60-2), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-{2-oxo-2-[ (2,2,2-trifluoroethyl)amino]ethyl}benzamide (known from WO2005 / 085216), 4-{5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl}-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}-1-naphthylcarboxamide (known from WO2009 / 002809), 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazine carboxylate methyl ester (known from WO2005 / 085216), 2-[2 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazine carboxylate (known from WO2005 / 085216), 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazine carboxylate (known from WO2005 / 085216), 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazine carboxylate (known from W Known from O2005 / 085216), 1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-2H-tetrazole-2-yl]methyl}-1H-pyrazole-5-carboxamide (known from WO2010 / 069502), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (known from CN102057925), 3-chloro-N-(2-cyanopropyl-2-yl)-N-[4-(1,1,1,2,3,3,[3-Hepheptafluoroprop-2-yl]-2-methylphenyl]phthalamide (known from WO2012 / 034472), 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (known from WO2010 / 129500), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothionylbutane-3-yl)benzamide (known from WO2012 / 034472), 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (known from WO2010 / 129500), 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (known from WO2010 / 129500), 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (known from WO2012 / 034472 ... Known from WO2009 / 080250), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothiacyclobutane-3-yl)benzamide (known from WO2012 / 029672), 1-[(2-chloro-1,3-thiazo-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidine-1-onthium-2-phenol salt (known from WO2009 / 099929), 1-[(6 [-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-onthium-2-phenol salt (known from WO2009 / 099929), (5S,8R)-1-[(6-chloropyridin-3-yl)methyl]-9-nitro-2,3,5,6,7,8-hexahydro-1H-5,8-epoxyimidazo[1,2-a]aza (known from WO2010 / 069266), (2E)-1-[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-imide Pentylhydrazine benzamide (known from WO2010 / 060231), 4-(3-{2,6-dichloro-4-[(3,3-dichloroprop-2-en-1-yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluoromethyl)pyrimidine (known from CN101337940), and N-[2-(tert-butylcarbamoyl)-4-chloro-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO2008 / 134969).

[0109] fungicides

[0110] The active ingredients identified in this article by their common names are known and documented, for example, in “Pesticide Manual” or on the Internet (e.g., http: / / www.alanwood.net / pesticides).

[0111] Biopesticides as a mixed component

[0112] Compounds of Formula I can be combined with biopesticides.

[0113] Biopesticides include, in particular, products produced by bacteria, fungi, yeast, plant extracts, and microorganisms, including proteins and secondary metabolites.

[0114] Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria, and bacteria that can act as biological insecticides, fungicides, or nematicides.

[0115] It also includes bacteria and fungi added as "inoculants" to plants or plant parts or organs, which promote plant growth and plant health through their special properties.

[0116] As a safety agent for mixed components

[0117] Compounds of Formula I may be combined with a safener, such as benoxacor, cloquintocet(-mexyl)), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole(-ethyl)), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen(-ethyl)), mefenpyr(-diethyl), oxabetrinil, 2-methoxy-N-{4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS... 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4).

[0118] In one embodiment, the insecticidal composition comprises a biologically effective amount of at least one of the pyridyl-substituted imidazolium ring compounds (component A), and at least one other active ingredient selected from the following compounds (component B):

[0119] (1) Acetylcholinesterase (AChE) inhibitors: acephate (CAS No.: 30560-19-1), chlorpyrifos (CAS No.: 2921-88-2);

[0120] (2) Sodium ion channel modulators: high-efficiency cypermethrin (CAS No.: 91465-08-6), bifenthrin (CAS No.: 82657-04-3), deltamethrin (CAS No.: 52918-63-5);

[0121] (3) Competitive modulators of nicotinic acetylcholine receptors (nAChR): (CN202410524442.X), Trifluoropyrimidine (CAS No.: 1263133-33-0), Acetamiprid (CAS No.: 135410-20-7), Imidacloprid (CAS No.: 138261-41-3), Thiamethoxam (CAS No.: 153719-23-4);

[0122] (4) Nicotinic acetylcholine receptor (nAChR) allosteric modulators: spinosad (CAS No.: 168316-95-8), ethyl spinosad (CAS No.: 935545-74-7);

[0123] (5) Allosteric regulators of glutamate-gated amino ion channels (GluCl): abamectin (CAS No.: 155569-91-8), avermectin (CAS No.: 71751-41-2);

[0124] (6) Uncoupling agents that interfere with proton gradient and affect oxidative phosphorylation: chlorfenapyr (CAS No.: 122453-73-0);

[0125] (7) Nicotinic acetylcholine receptor (nAChR) channel blockers: Insecticidal monoclonal antibody (CAS No.: 29547-00-0);

[0126] (8) Chitin biosynthesis inhibitors that affect chitin synthase 1: Lufenuron (CAS No.: 103055-07-8);

[0127] (9) Ecdysone receptor agonist: methoxyfenozide (CAS No.: 161050-58-4);

[0128] (10) Voltage-dependent sodium ion channel blocker: indoxacarb (CAS No.: 173584-44-6);

[0129] (11) Ryedin receptor modulators: chlorantraniliprole (CAS No.: 500008-45-7), bromocyanamide (CAS No.: 736994-63-1);

[0130] (12) GABA-gated chloride channel allosteric modulators: oxadiazon (CAS No.: 2892524-05-7), bromoxynil (CAS No.: 1207727-04-5), isoxadiazon (CAS No.: 2061933-85-3), cyclopropionibacterium (CAS No.: 2375110-88-4);

[0131] (13) String modulator - unknown target site: flupyradifurone (CAS No.: 158062-67-0);

[0132] (14) TRPV channel modifier for string instruments: Pymetrozine (CAS No.: 123312-89-0) (CN202411096509.0);

[0133] (15) Chitin biosynthesis inhibitor (type 1): Thiazidinone (CAS No.: 69327-76-0);

[0134] (16) Acetylcholinesterase (AChE) inhibitor: malathion (CAS No.: 121-75-5);

[0135] (17) Inhibitor of mitochondrial electron transport complex (I): Pyridaben (CAS No.: 96489-71-3);

[0136] (18) Acetyl-CoA carboxylase inhibitor: Spirotetracycline (CAS No.: 203313-25-1);

[0137] (19) Mechanism of action unknown: (CN202410765633.5) (CN202410272761.6).

[0138] In another specific embodiment, the weight ratio of active ingredients A and B in the composition is 1:1000-100:1, 1:500-80:1, 1:400-50:1, 1:300-30:1, 1:200-20:1, 1:150-10:1, 1:100-5:1, 1:80-1:1, 1:50-1:5, or 1:20-1:10.

[0139] Plants and plant parts

[0140] All plants and plant parts can be processed according to the present invention. In this document, "plant" is understood to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants), such as cereals (wheat, rice, rye, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes, peas and other vegetable species, cotton, tobacco, rapeseed, and fruit plants (having fruits such as apples, peas, citrus fruits, and grapes). Crop plants can be plants obtained through conventional breeding and optimization methods or through biotechnological methods or genetic engineering methods or combinations thereof, including transgenic plants and cultivars, including those protected and unprotected by plant breeders' rights. Plant parts should be understood to mean all above-ground and below-ground parts and organs of a plant, such as buds, leaves, flowers, and roots, with examples given being leaves, needles, stems, trunks, flowers, fruiting bodies, fruits and seeds, as well as tubers, roots, and rhizomes. Plant parts also include harvested materials as well as materials for asexual and sexual reproduction, such as cuttings, tubers, rhizomes, slips, and seeds.

[0141] The treatment of plants and plant parts by the present invention using compounds of Formula I is carried out directly by conventional treatment methods or by applying the compounds to their environment, habitat or storage space, such conventional treatment methods as impregnation, spraying, evaporation, atomization, dispersing, spraying, injection, and, in the case of propagation materials, especially seeds, one or more layers of coating may also be applied.

[0142] As described above, all plants and their parts can be treated according to the present invention. In one preferred embodiment, wild plant species and cultivars, or those obtained through conventional biological breeding such as crossbreeding or protoplast fusion, and their parts are treated. In another preferred embodiment, transgenic plants and cultivars (genetically modified organisms) obtained through genetic engineering—which can be combined with conventional methods if appropriate—and their parts are treated. The terms "part" or "plant part" have been explained above. Particularly preferred are those commercially available conventional cultivars or those currently in use, treated according to the present invention. Cultivars are understood to mean plants with new performance "characteristics" that have been obtained through conventional breeding, through mutation, or through recombinant DNA technology. They can be cultivars, varieties, biotypes, or genotypes.

[0143] Genetically modified plants, seed treatment, and integration events.

[0144] Preferred transgenic plants or plant cultivars (obtained through genetic engineering) treated according to the present invention include all plants that have undergone genetic modification and received genetic material that endows these plants with particularly advantageous and useful properties. Examples of such properties include: better plant growth, enhanced tolerance to high or low temperatures, enhanced tolerance to drought or to water levels or soil salinity, improved flowering performance, easier harvesting, accelerated maturation, higher yield, higher quality and / or higher nutritional value of the harvested product, longer shelf life and / or processability of the harvested product. Other, and particularly emphasized, examples of this property include enhanced plant resistance to animal and microbial pests, such as insects, arachnids, nematodes, mites, slugs, and snails, for example, due to toxins formed in the plant, particularly those formed in the plant through genetic material from Bacillus thuringiensis (e.g., through genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb, and CryIF and combinations thereof); enhanced plant resistance to plant pathogenic fungi, bacteria, and / or viruses, induced, for example, by systemically acquired resistance (SAR), systemins, phytoalexins, inducers, and resistance genes, as well as corresponding expressed proteins and toxins; and increased plant tolerance to specific active insecticidal ingredients, such as imidazolinones, sulfonylureas, glyphosate, or glufosinate (e.g., the "PAT" gene). Genes conferring the desired traits can exist in transgenic plants in a combined form. Examples of transgenic plants include important crop plants such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes, peas and other types of vegetables, cotton, tobacco, rapeseed, and fruit plants (with fruits such as apples, pears, citrus fruits and grapes), with particular emphasis on corn, soybeans, wheat, rice, potatoes, cotton, sugarcane, tobacco, and rapeseed. A particularly emphasized trait is enhanced plant resistance to insects, arachnids, nematodes, slugs, and snails.

[0145] Crop protection – types of treatment

[0146] Treatment of plants and plant parts with compounds of Formula I can be carried out directly by conventional treatment methods or by applying the compounds to their environment, habitat, or storage space. These conventional treatment methods include, for example, soaking, spraying, misting, irrigation, evaporation, dusting, atomization, broadcasting, foaming, coating, spreading, injection, watering (soaking), and drip irrigation. In the case of propagation materials, especially seeds, methods such as dry seed treatment, wet seed treatment, suspension treatment, crusting, and coating with one or more layers can also be used. Compounds of Formula I can also be applied using ultra-low-dose methods or injected into the soil in their intended form or the compound itself.

[0147] A preferred direct treatment for plants is foliar application, which means applying the compound of Formula I to the leaves, wherein the treatment frequency and application rate should be adjusted according to the level of infection of the pest.

[0148] In the case of systemically active compounds, compounds of Formula I can also enter the plant via the root system. The plant then treats the plant's habitat by acting on the compound of Formula I. This can be accomplished, for example, by infiltration; or by mixing into the soil or nutrient solution, meaning that the plant site (e.g., soil or hydroponic system) is filled with the liquid form of the compound of Formula I; or by soil application, meaning that the compound of Formula I is introduced into the plant site in solid form (e.g., in granular form). In the case of rice crops, this can also be accomplished by metering the compound of Formula I into the flooded paddy field in solid application form (e.g., as granules).

[0149] Seed treatment

[0150] The control of animal pests through seed treatment is a well-established and continuously evolving topic. However, seed treatment involves a number of problems that are not always satisfactorily resolved. Therefore, there is a need to develop methods for protecting seeds and germinating crops that do not require, or at least significantly reduce, the additional application of pesticides during storage, after sowing, or after emergence. It is also necessary to optimize the amount of active ingredient used to provide optimal protection for seeds and germinating plants against animal pests without harming the plant itself. In particular, methods for seed treatment should also take into account the inherent insecticidal and / or nematicidal properties of pest-resistant or pest-tolerant transgenic plants to achieve optimal protection for seeds and germinating plants with minimal use of crop protection products.

[0151] Therefore, more particularly, the present invention also relates to a method for protecting seeds and germinating plants from pests by treating seeds with one of the compounds of Formula I. The method of the present invention for protecting seeds and germinating plants from pests also includes a method in which seeds are treated simultaneously with a compound of Formula I and a mixture thereof in one operation or continuously. It also includes a method of treating seeds with a compound of Formula I and a mixture thereof at different times.

[0152] The present invention also relates to the use of compounds of formula I for treating seeds to protect the seeds and the resulting plants from animal pests.

[0153] The present invention further relates to seeds treated with a compound of Formula I to protect them from animal pests. The present invention also relates to seeds treated simultaneously with a compound of Formula I and a mixed component. The present invention further relates to seeds treated with a compound of Formula I and a mixed component at different times. In the case of seeds treated with a compound of Formula I and a mixed component at different times, the components may be present in different layers of the seed. In this case, the layers containing the compound of Formula I and the mixed component may optionally be separated by an intermediate layer. The present invention also relates to seeds in which a compound of Formula I and a mixed component have been applied as part of a coating or other layer, or in addition to a coating.

[0154] The present invention also relates to seeds that, after being treated with a compound of formula I, undergo a film coating process to prevent the seeds from being abraded by dust.

[0155] One advantage of using one of the compounds of Formula I systematically is that the seed treatment protects not only the seed itself but also the plant derived from it (after emergence) from animal pests. In this way, direct treatment of the crop at sowing or shortly thereafter can be eliminated.

[0156] A further advantage is that treating seeds with the compound of formula I can promote germination and emergence of the treated seeds.

[0157] Also considered advantageous is that compounds of formula I can be used, especially, for genetically modified seeds.

[0158] Compounds of Formula I can also be used in combination with signaling technology components, resulting in, for example, better colonization of symbionts, such as rhizobia, mycorrhizae and / or endophytic bacteria or fungi, and / or optimized nitrogen fixation.

[0159] Compounds of Formula I are suitable for protecting the seeds of any plant variety used in agriculture, greenhouses, forestry, or horticulture. More particularly, said seeds include the seeds of cereals (e.g., wheat, barley, rye, millet, and oats), corn, cotton, soybeans, rice, potatoes, sunflowers, coffee beans, tobacco, rapeseed, canola, sugar beets (e.g., sugar beets and forage beets), peanuts, vegetables (e.g., tomatoes, cucumbers, beans, cruciferous plants, onions, lettuce), fruit plants, turfgrasses, and ornamental plants. Of particular importance are the seeds of cereals (wheat, barley, rye, oats), corn, soybeans, cotton, rapeseed, canola, and rice.

[0160] As mentioned above, treatment of transgenic seeds with compounds of Formula I is also particularly important. These seeds typically comprise seeds of plants containing a heterologous gene expressing at least one polypeptide with insecticidal and / or nematicidal properties. The heterologous gene in the transgenic seed may originate from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus, or Gliocladium. The compositions of the present invention are particularly suitable for treating transgenic seeds containing at least one heterologous gene derived from Bacillus. More preferably, the heterologous gene is derived from Bacillus thuringiensis.

[0161] In the context of this invention, the compound of formula I is applied to seeds. It is preferable to treat the seeds in a state that is sufficiently stable so that no damage occurs during treatment. Generally, seeds can be treated at any point between harvesting and sowing. Seeds that have been isolated from the plant and from which the rachis, outer shell, stem, epidermis, hairs, or pulp have been removed are typically used. For example, seeds that have been harvested, cleaned, and dried to a moisture content suitable for storage can be used. Alternatively, seeds that have been dried, for example, treated with water again, and then dried again (e.g., irrigation) can also be used.

[0162] Generally, when treating seeds, it is essential to ensure that the amount of Formula I compound and / or other additives applied to the seeds is chosen such that seed germination and the resulting plant are not impaired. This must be especially ensured in cases where active ingredients may exhibit toxic effects on plants at certain application rates.

[0163] Compounds of Formula I are typically applied to seeds in suitable formulations. Suitable formulations and seed treatment methods are known to those skilled in the art.

[0164] Compounds of Formula I can be converted into conventional seed coating formulations, such as solutions, emulsions, suspensions, powders, foams, slurries, or other seed coating compositions, as well as ULV formulations.

[0165] These formulations are prepared in a known manner by mixing a compound of Formula I with conventional additives, such as conventional fillers and solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins, and water.

[0166] Useful colorants that may be present in the seed dressing formulations used according to the invention are all colorants commonly used for the purposes described herein. Pigments that are slightly soluble in water can be used, or water-soluble dyes can be used. Examples include known colorants named Rhodamine B, CI Pigment Red 112, and CI Solvent Red 1.

[0167] Useful wetting agents that may be present in the seed dressing formulations used according to the invention are all substances that promote wetting and are generally used in formulations of active agricultural chemicals. Alkyl naphthalene sulfonates, such as diisopropyl naphthalene sulfonate or diisobutyl naphthalene sulfonate, are preferred.

[0168] Useful dispersants and / or emulsifiers that may be present in seed dressing formulations used according to the invention are all nonionic, anionic, and cationic dispersants commonly used in formulations of active agrochemical ingredients. Nonionic or anionic dispersants, or mixtures of nonionic or anionic dispersants, are preferred. Suitable nonionic dispersants particularly include ethylene oxide / propylene oxide block copolymers, alkylphenol polyethylene glycol ethers, and tristyrylphenol polyethylene glycol ethers, as well as their phosphorylated or sulfated derivatives. Suitable anionic dispersants are especially lignin sulfonates, polyacrylates, and aryl sulfonate / formaldehyde condensates.

[0169] The defoamer that may be present in the seed dressing formulation used according to the present invention is any foam inhibitor commonly used in formulations of active agrochemical ingredients. Silicone defoamers and magnesium stearate are preferred.

[0170] Preservatives that may be present in the seed dressing formulations used according to the present invention are all substances that can be used for this purpose in agricultural chemical compositions. Examples include dichlorophenol and benzyl alcohol hemiacetal.

[0171] The secondary thickener that may be present in the seed dressing formulation used according to the present invention is any substance that can be used for this purpose in an active agrochemical composition. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clay, and finely dispersed silica.

[0172] Useful adhesives that can be present in the seed dressing formulations used according to the present invention are all conventional adhesives that can be used in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, and tylose.

[0173] The gibberellins that can be present in the seed dressing formulation used according to the present invention are preferably gibberellins A1, A3 (=gibberellic acid), A4 and A7, with gibberellic acid being particularly preferred.

[0174] The seed dressing formulations used according to the present invention can be used directly or after pre-diluting with water to treat a variety of different types of seeds. For example, concentrates or formulations obtained therefrom by dilution with water can be used to coat the following seeds: seeds of cereals (such as wheat, barley, rye, oats, and triticale), and seeds of corn, rice, rapeseed, peas, beans, cotton, sunflower, soybeans, and sugar beets, or a variety of different vegetable seeds. The seed dressing formulations used according to the present invention, or their diluted forms, can also be used to treat the seeds of genetically modified plants.

[0175] For treating seeds with the seed dressing formulation used according to the present invention or in a form prepared therefrom, all conventional mixing equipment used for seed dressing is available. More specifically, the seed dressing process involves placing seeds in batches or continuously in a mixer; adding the desired amount of the seed dressing formulation, either on its own or pre-diluted with water; and mixing until the formulation is evenly distributed on the seeds. If appropriate, a drying operation may then be performed.

[0176] The application rate of the seed dressing formulation used according to the present invention can vary within a relatively wide range. It depends on the specific content of the compound of Formula I in the formulation and the seeds. The application rate of the compound of Formula I is typically from 0.001 g to 50 g per kilogram of seeds; preferably from 0.01 g to 15 g per kilogram of seeds.

[0177] For animal health

[0178] In the field of animal health, i.e., veterinary medicine, the active ingredient of this invention is used to combat animal parasites, particularly ectoparasites or, in other embodiments, endoparasites. The term "endoparasites" particularly includes worms such as tapeworms, nematodes, or flukes; and protozoa such as coccidia. Ectoparasites are generally and preferably arthropods, especially insects such as flies (biting flies and sucking flies), parasitic fly larvae, lice, hair lice, bird lice, fleas, etc.; or scabies mites such as ticks, such as hard ticks or soft ticks; or mites such as scabies mites, fall mites, and bird mites; and aquatic ectoparasites such as copepods.

[0179] In the field of veterinary medicine, compounds of formula I with good homeothermic toxicity are suitable for the prevention and treatment of parasites and are found in animal breeding and animal husbandry of livestock, breeding animals, zoo animals, laboratory animals, experimental animals, and domestic animals. They are effective against parasites at all or specific developmental stages.

[0180] Agricultural livestock include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer, and especially cattle and pigs; poultry such as turkeys, ducks, geese, and especially chickens; aquaculture such as fish and crustaceans; and insects such as bees.

[0181] Domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, especially dogs, cats, caged birds, reptiles, amphibians, and ornamental fish.

[0182] In a preferred embodiment, the compound of Formula I is administered to a mammal.

[0183] In another preferred embodiment, the compound of formula I is administered to poultry, i.e., caged birds and especially poultry.

[0184] The use of compounds of Formula I to control animal parasites aims to reduce or prevent disease, mortality, and performance loss (in the case of meat, milk, wool, raw hides, eggs, honey, etc.), so as to make animal husbandry more economical and simpler, and to achieve better maintenance of animal health.

[0185] In the field of animal health, the term "control" or "controlling" refers to compounds of Formula I that are effective in reducing the incidence of specific parasites in animals infected with such parasites to a harmless level. More specifically, in this context, "control" refers to compounds of Formula I that can kill the parasites, inhibit their growth, or suppress their proliferation.

[0186] Typically, the active ingredients of this invention can be used directly when treating animals. They are preferably used (administered) in the form of pharmaceutical compositions that may contain pharmaceutically acceptable excipients and / or adjuvants known in the art.

[0187] In animal health and animal husbandry, the active ingredient is used (administered) in the following known ways: enteral administration, in the form of tablets, capsules, potions, drench, granules, pastes, bolus, feed-through process, and suppositories; parenteral administration, such as by injection (intramuscular, subcutaneous, intravenous, especially intraperitoneal), implantation; nasal administration; skin administration, in the form of, for example, immersion or bathing, spraying, infusion and dripping, detergents and powders; and by means of molded articles containing the active ingredient, such as collars, ear tags, tail tags, limb bands, halters, marking devices, etc. The active ingredient can be formulated into shampoos or suitable formulations that can be applied in the form of aerosols or non-pressurized sprays such as pump sprays and nebulizers.

[0188] When used for livestock, poultry, pets, etc., the active ingredients of the present invention may be used directly or after dilution (e.g., 100 to 10,000 times dilution) in formulations containing 1% to 80% by weight of the active ingredients, or they may be used as a chemical bath.

[0189] In applications in animal health, to broaden the activity spectrum, the active ingredients of the present invention can be used in combination with suitable synergists, anthelmintics, or other active ingredients, such as acaricides, insecticides, anthelmintics, and antiprotozoa agents.

[0190] Vector control

[0191] Compounds of Formula I can also be used for vector control. In the context of this invention, vectors are arthropods, particularly insects or arachnids, capable of transmitting pathogens such as viruses, worms, single-celled organisms, and bacteria from a host (plant, animal, human, etc.) to a host. Pathogens can be transmitted to a host mechanically (e.g., trachoma in non-stinging flies) or after injection (e.g., malaria parasites in mosquitoes).

[0192] In the context of this invention, examples of disease vectors are insects, such as aphids, flies, leafhoppers, or thrips, which can transmit plant viruses to plants. Other vectors capable of transmitting plant viruses include spider mites, lice, beetles, and nematodes.

[0193] In the context of this invention, other examples of disease vectors are insects and arachnids, such as mosquitoes, especially mosquitoes of the genera Aedes and Anopheles, such as Anopheles gambiae, Anopheles arbiensis, Anopheles funestus, and Anopheles dirus (malaria); as well as mosquitoes of the genus Culex, lice, fleas, flies, mites, and ticks, which can transmit pathogens to animals and / or humans.

[0194] If the compound of formula I is resistant to damage, then vector control is also possible.

[0195] Compounds of Formula I are suitable for use in the prevention of vector-borne diseases and / or pathogens. Therefore, another aspect of the invention is the use of compounds of Formula I in, for example, agriculture, horticulture, forestry, landscaping, and recreational facilities, as well as in the protection of materials and stored products for vector control.

[0196] Protection of industrial materials

[0197] Compounds of Formula I are suitable for protecting industrial materials from insect attack or damage, such as from insects of the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psciformes, and Zygentoma.

[0198] In this context, industrial materials should be understood to mean inanimate materials, such as, preferably, plastics, adhesives, glues, paper and paper sheets, leather, wood and processed wood products, and coating compositions. The use of this invention for the protection of wood is particularly preferred.

[0199] In another embodiment, the compound of formula I is used in conjunction with at least one other insecticide and / or at least one fungicide.

[0200] In another embodiment, the compounds of Formula I are ready-to-use insecticides, meaning they can be applied to the material without further modification. In particular, suitable other insecticides or fungicides are those mentioned above.

[0201] Surprisingly, compounds of Formula I have also been found to protect objects in contact with saltwater or brackish water from contamination, particularly ship hulls, screens, nets, structures, mooring equipment, and signaling systems. It is also possible that compounds of Formula I can be used alone or in combination with other active ingredients as antifouling agents.

[0202] Control of animal pests in the health field

[0203] Compounds of Formula I are suitable for the control of animal pests in the sanitation field. More specifically, the present invention can be used in the household, sanitation, and storage product protection fields, particularly for the control of insects, arachnids, and mites in enclosed spaces such as residences, factory workshops, offices, and vehicle cabins. For the control of animal pests, compounds of Formula I can be used alone or in combination with other active ingredients and / or adjuvants. They are preferably used in household insecticide products. Compounds of Formula I are effective against both susceptible and resistant species and at all developmental stages.

[0204] These pests include, for example, those from the following classes: Arachnida; Scorpiones, Araneae, and Opiliones; Chilopoda and Diplopoda; Blattodea; Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psciformes, Saltatoria, Orthoptera, Siphonaptera, and Silverfish; and Malacostraca, Isopoda.

[0205] In baits or bait stations used for deployment, application is carried out in the following forms: aerosols, unpressurized spray products such as pump-action and atomizing sprays, automatic fogging systems, smoke agents, foaming agents, gels, evaporating products with evaporator tablets made of cellulose or plastic, liquid evaporators, gel and film evaporators, propeller-driven evaporators, energy-free or passive evaporation systems, moth traps, moth traps, and moth trap glue; as granules or powders. Detailed Implementation

[0206] The following examples are for illustrative purposes only and should not be construed as limiting the invention in any way. The scope of protection of this invention is defined by the claims.

[0207] Given the economic efficiency and diversity of the compounds, we preferentially synthesized a number of compounds, some of which are listed in Table 1 below. The specific compound structures and corresponding compound information are shown in Table 1. The compounds in Table 1 are only for better illustration of the present invention and do not limit the invention. Those skilled in the art should not interpret this as limiting the scope of the above-mentioned subject matter of the invention to the following compounds.

[0208] Table 1. Compound structures and their properties 1 H NMR

[0209] Several methods for preparing the compounds of the present invention are described in detail in the following schemes and examples. The raw materials can be commercially available or prepared by methods known in the literature or as detailed in the description. Those skilled in the art will understand that other synthetic routes can also be used to synthesize the compounds of the present invention. Although specific raw materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar raw materials and conditions. Such variations or modifications to the preparation methods of the present invention, such as various isomers of the compounds, are all included within the scope of the present invention. Furthermore, the preparation methods described below can be further modified according to the disclosure of the present invention using conventional chemical methods well known to those skilled in the art. For example, protecting appropriate groups during the reaction process, etc.

[0210] The following method examples are provided to further illustrate the preparation methods of the present invention. The specific substances, types, and conditions used are intended to further explain the invention and are not intended to limit its reasonable scope. The reagents used in the synthetic compounds shown below are either commercially available or can be easily prepared by those skilled in the art.

[0211] Examples of representative compounds are given below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0212] 1. Synthesis of Compound 1

[0213] Compound 1-1 (496 mg, 1 mmol) was dissolved in 20 mL of 1,4-dioxane. Then, 2-chloro-5-(difluoromethoxy)pyrimidine (0.36 g, 2 mmol) and cesium fluoride (0.3 g, 2 mmol) were added sequentially, followed by 2 mL of H₂O. After purging with nitrogen, a catalytic amount of 1,1'-bis(diphenylphosphine)ferrocene palladium(II) dichloromethane complex was added. The temperature was slowly raised to 100 °C, and the reaction was carried out for 12 h. The reaction was monitored until the starting material disappeared. The reaction solution was concentrated, and the residue was extracted three times with ethyl acetate and washed three times with saturated brine. After drying with anhydrous sodium sulfate, the sample was stirred and passed through a column. The fraction was evaporated to dryness to give compound 1 as 0.3 g (yield 58.3%), a white solid.

[0214] 2. Synthesis of Compound 2

[0215] Dissolve 2-1 (100 mg, 0.47 mmol) in 10 mL of dioxane, add 1-1 (354 mg, 0.71 mmol), copper(I)thiophene-2-carboxylic acid (268 mg, 1.41 mmol), replace with N2, add tetra(triphenylphosphine)palladium (54 mg, 0.047 mmol), microwave at 130 °C for 45 min, monitor the reaction until the starting material disappears, add silica gel directly to the reaction solution and stir, then separate by normal phase (0–20% EA / PE). Dry the organic phase to give 2 (25 mg, 10% yield), a white solid.

[0216] 3. Synthesis of Compound 5

[0217] (1) In a 50 mL single-necked flask, dissolve 5-1 (200 mg, 0.40 mmol) in 5 mL of 1,4-dioxane, add potassium acetate (79 mg, 0.80 mmol) and pinacol diborate (153 mg, 0.60 mmol), purge once with nitrogen, add Pd(dppf)Cl2 (29 mg, 0.04 mmol), purge three times with nitrogen, and stir at 100 °C for 4 h. Monitor the reaction for completeness using LC-MS. The crude product from the reaction solution is used directly in the next step.

[0218] (2) To the crude product from step one, add 5 ml of 1,4-dioxane and 1 ml of water, then add cesium fluoride (182 mg, 1.20 mmol) and 2-chloro-5-(difluoromethoxy)pyrimidine (108 mg, 0.60 mmol), purge once with nitrogen, then add Pd(dppf)Cl2 (29 mg, 0.04 mmol), purge three times with nitrogen, and stir at 100 °C for 12 h. Monitor the reaction for completeness using LCMS. Quench the reaction solution with water, extract with ethyl acetate, wash the organic phase with water and saturated brine, dry and concentrate, and purify the residue by column chromatography (EA / PE = 2 / 3) to give compound 5 (78 mg, 34%) as a white solid.

[0219] 4. Synthesis of Compound 31

[0220] Substrate 1-1 (250 mg, 0.504 mmol) was dissolved in 10 mL of dioxane and 1 mL of H₂O in a single-necked flask. Cesium carbonate (229.6 mg, 1.512 mmol) and compound 31-1 (133.5 mg, 0.554 mmol) were added. The mixture was purged with nitrogen three times. DPPF palladium dichloride catalyst (20 mg, 0.025 mmol) was added, and the mixture was purged with nitrogen three more times. The reaction was carried out at 100 °C for 8 h. The reaction was monitored by LCMS to indicate completion. The reaction solution was filtered through diatomaceous earth, extracted with water / EA, and the organic phase was dried, concentrated, and purified by column chromatography (EA / PE = 1 / 2) to give product 31 (120 mg, 44.9%) as a white solid.

[0221] 5. Synthesis of Compound 33

[0222] Starting material 1-1 (2 g, 4.03 mmol) and 2-chloro-4-(difluoromethoxy)-5-fluoropyridine (796 mg, 4.03 mmol) were dissolved in 60 mL of dioxane and 6 mL of water, followed by the addition of cesium fluoride (1.84 g, 12.09 mmol). The system was protected under nitrogen, and a catalytic amount of catalyst Pd(dppf)Cl2 was added, followed by nitrogen protection. The reaction was carried out overnight at 100°C. The reaction was monitored until the starting material disappeared, at which point the reaction was terminated. Post-treatment: The reaction solution was concentrated and purified under normal phase to give product 33 (1 g, yield 54.0%), a white solid.

[0223] 6. Synthesis of Compound 45

[0224] Compound 45-1 was prepared as described in section 5-2 above. Then, in a 50 mL single-necked flask, the starting material 45-1 (200 mg, 0.39 mmol) and 2-chloro-5-(difluoromethoxy)pyrimidine (106 mg, 0.59 mmol) were dissolved in 10 mL of a mixed solution of 1,4-dioxane and water (V1,4-dioxane:Vwater = 10:1). Potassium carbonate (162 mg, 1.18 mmol) was added, and the mixture was purged with nitrogen three times. Pd(dppf)Cl2.CH2Cl2 (6 mg, 0.01 mmol) was added, and the mixture was purged with nitrogen three more times. The mixture was reacted at 90 °C for 3 h. The reaction was monitored to ensure complete reaction. The reaction solution was cooled to room temperature, and silica gel powder was added and mixed. The mixture was purified in normal phase, and the fraction was evaporated to dryness to obtain product 45 (100 mg, yield 48%), a white solid.

[0225] 7. Synthesis of Compound 46

[0226] (1) In a 50 mL single-necked flask, compound 46-1 (500 mg, 2.87 mmol) was dissolved in 5 mL of N,N-dimethylformamide, and potassium carbonate (595 mg, 4.30 mmol) and 1,1-difluoro-2-iodoethane (1100 mg, 5.71 mmol) were added. The reaction was carried out at 50 °C for 10 h. The reaction was monitored by LCMS until complete. The reaction solution was quenched with water, extracted with ethyl acetate, and the organic phase was washed with water and saturated brine. The solution was dried and concentrated, and the residue was purified by column chromatography (EA / PE = 1 / 5) to give compound 46-2 (600 mg, 87.84%), a pale yellow liquid.

[0227] (2) In a 50 mL single-necked flask, 1-1 (200 mg, 0.40 mmol) was dissolved in 10 mL of 1,4-dioxane and 1 mL of water. Cesium fluoride (182.28 mg, 1.20 mmol) and compound 46-2 (142.80 mg, 0.60 mmol) were added. The mixture was purged with nitrogen once. Pd(dppf)Cl2 (29 mg, 0.04 mmol) was added, and the mixture was purged with nitrogen three times. The mixture was stirred at 100 °C for 12 h. The reaction was monitored by LCMS until complete. The reaction solution was quenched with water and extracted with ethyl acetate. The organic phase was washed with water and saturated brine, dried and concentrated. The residue was purified by column chromatography (EA / PE = 1 / 3) to give compound 46 (110 mg, 52.08%), a pale yellow solid.

[0228] 8. Synthesis of Compound 49

[0229] (1) Compound 49-1 (4.6 g crude product, 0.022 mol), compound 49-2 (5.76 g, 0.022 mol) and HATU (12.54 g, 0.033 mol) were dissolved in DCM. Triethylamine (6.67 g, 0.066 mol) was slowly added and stirred at room temperature for 3 h. After the reaction was completed, water and DCM were added for extraction, and the mixture was dried and concentrated to obtain crude compound 49-3, which was directly used in the next step.

[0230] (2) The crude compound 49-3 was dissolved in acetic acid and heated to 120°C overnight. After the reaction was completed, the mixture was concentrated, extracted with water and EA, and purified in normal phase to obtain compound 49-4 (3.5 g, 8.10 mmol).

[0231] (3) Compound 49-4 (3.5 g, 8.10 mmol) was dissolved in DCM, and m-CPBA (3.63 g, 17.82 mmol, 85%) was added in portions. The mixture was stirred at room temperature for 2 h. After the reaction was completed, sodium thiosulfate aqueous solution, sodium bicarbonate aqueous solution and saturated brine were added for washing. After drying, the mixture was concentrated to obtain compound 19-5 (3.5 g, 7.54 mmol, yield 93%).

[0232] (4) Compound 49-5 (0.30 g, 0.65 mmol), B2Pin2 (0.41 g, 1.63 mmol), and KOAc (0.19 g, 1.95 mmol) were dissolved in 1,4-dioxane and purged twice with nitrogen. Pd(dppf)Cl2.CH2Cl2 (26.6 mg, 0.033 mmol) was added and purged three more times with nitrogen. The reaction was carried out overnight at 100 °C. The reaction was monitored to ensure complete reaction. The reaction solution was cooled to room temperature, silica gel powder was added and mixed, and the mixture was purified in normal phase to obtain compound 49-6 (0.20 g, 0.39 mmol, yield 60%).

[0233] (5) Compound 49-6 (0.20 g, 0.39 mmol), 2-chloro-5-(difluoromethoxy)pyrimidine (0.11 g, 0.59 mmol), and CsF (0.18 g, 1.17 mmol) were dissolved in a mixed solution of 1,4-dioxane and water (V1,4-dioxane:Vwater = 10:1). The solution was purged with nitrogen twice. Pd(dppf)Cl2.CH2Cl2 (15.9 mg, 0.020 mmol) was added, and the solution was purged with nitrogen three more times. The reaction was carried out overnight at 100 °C. The reaction was monitored to ensure complete reaction. The reaction solution was cooled to room temperature, silica gel powder was added and mixed, and the solution was purified in normal phase to obtain compound 49 (32 mg, 0.06 mmol, yield 15%).

[0234] 9. Synthesis of Compound 64

[0235] (1) Dissolve 64-1 (5g, 22.1mmol) in 80mL THF and add it to a 250mL single-necked flask. Cool to 0℃, add sodium hydrogen (0.97g, 24.2mmol), keep warm at 0℃ and react for 1h. Add isopropyl mercaptan (1.8g, 24.2mmol), keep warm at 0℃ and react for 2h. Monitor the reaction until the starting material disappears. Add water to quench the reaction. Extract three times with ethyl acetate, wash three times with saturated brine, and evaporate to dryness to obtain crude product 64-2 (4.6g, yield 71.4%).

[0236] (2) Dissolve 64-2 (4.6 g, 18 mmol) in 80 mL MeOH, add sodium hydroxide (2.1 g, 54 mmol), heat to 70 °C, and react for 5 h, monitoring the reaction until the starting material disappears. Concentrate the reaction solution, then add EA / H2O, adjust the acid, extract and separate the layers, and wash with saturated brine. Dry with anhydrous sodium sulfate and then evaporate to dryness to obtain 64-3 (3.9 g, yield 79.6%).

[0237] (3) Dissolve 64-3 (3.9 g, 14.2 mmol) in 50 mL of DCM, and add 5-trifluoromethyl-3-amino-2-methylaminopyridine (4.06 g, 21.3 mmol), TEA (4.3 g, 42.6 mmol), and HATU (6.47 g, 17.1 mmol) sequentially. React at room temperature for 12 h, monitoring the reaction until the starting material disappears. Add water to the reaction solution, extract three times with DCM, and wash three times with saturated brine. Dry the solution with anhydrous sodium sulfate and then evaporate to dryness to obtain crude 64-4 (3.5 g, yield 55.6%).

[0238] (4) Dissolve 64-4 (3.5 g, 7.8 mmol) in 100 mL of glacial acetic acid, heat to 120 °C, and react for 3 h, monitoring the reaction until the starting material disappears. Concentrate the reaction solution, extract three times with ethyl acetate, and wash three times with saturated brine. After drying with anhydrous sodium sulfate, mix the sample and pass it through a column. The fraction was evaporated to dryness to obtain 64-5 (2.9 g, yield 87.9%).

[0239] (5) Dissolve 64-5 (2.9 g, 6.7 mmol) in 50 mL of DCM, add m-chloroperoxybenzoic acid (3.44 g, 16.7 mmol), and react at room temperature for 2 h, monitoring the reaction until the starting material disappears. Quench the reaction solution with sodium thiosulfate solution, extract with DCM, wash three times with saturated sodium bicarbonate solution, and wash three times with saturated brine. After drying with anhydrous sodium sulfate, mix the sample and pass it through a column, then evaporate the distillate to dryness to obtain 64-6 (2.6 g, yield 83.9%).

[0240] (6) Dissolve 64-6 (200 mg, 0.4 mmol) in 30 mL of 1,4-dioxane, then add pinacol diboronate (202 mg, 0.8 mmol) and potassium acetate (118 mg, 1.2 mmol) sequentially. After purging with nitrogen, add a catalytic amount of 1,1'-bis(diphenylphosphine)ferrocene palladium(II) dichloromethane complex, slowly raise the temperature to 100 °C, and react for 12 h, monitoring the reaction until the starting material disappears. Concentrate the reaction solution, extract the residue three times with ethyl acetate, and wash three times with saturated brine. Dry the residue with anhydrous sodium sulfate and then evaporate to dryness to obtain crude product 64-7 (0.2 g, yield 90.1%).

[0241] (7) Dissolve 64-7 (0.2 g, 0.39 mmol) in 30 mL of 1,4-dioxane, then add 2-chloro-5-(difluoromethoxy)pyrimidine (86.5 mg, 0.58 mmol), potassium carbonate (107 mg, 0.78 mmol), and 3 mL of H2O sequentially. After purging with nitrogen, add a catalytic amount of 1,1'-bis(diphenylphosphine)ferrocene palladium(II) dichloromethane complex, slowly raise the temperature to 100 °C, and react for 12 h. Monitor the reaction until the starting material disappears. Concentrate the reaction solution, extract the residue three times with ethyl acetate, and wash three times with saturated brine. After drying with anhydrous sodium sulfate, mix the sample and pass it through a column. The fraction was evaporated to dryness to obtain 64 (83 mg, yield 40.1%).

[0242] 10. Synthesis of compounds 70 and 73

[0243] (1) 73-1 (3.5 g, 11.8 mmol) was added to 100 mL of DCM in a single-necked flask, followed by the addition of TEA (1.78 g, 17.7 mmol), HATU (6.72 g, 17.7 mmol), and compound 49-2 (3.06 g, 11.8 mmol). The mixture was stirred at room temperature for 12 h. The mixture was then diluted with DCM, and the organic phase was washed successively with water, 1 M hydrochloric acid, and saturated sodium bicarbonate. The organic phase was evaporated to dryness to obtain crude product 73-2, which was used directly in the next step without further treatment.

[0244] (2) Dissolve the crude product 73-2 from the previous step in 50 mL of acetic acid in a single-necked flask and stir at 120 °C for 12 h. After concentrating the acetic acid off under reduced pressure, dilute the reaction solution with ethyl acetate, wash the organic phase with water, collect the organic phase, dry and concentrate to obtain crude product 73-3. The crude product is used directly in the next step without any treatment.

[0245] (3) The crude product 73-3 from the previous step was dissolved in 60 mL of DCM in a single-necked flask, and m-chloroperoxybenzoic acid (4.77 g, 23.6 mmol) was added. The reaction was carried out at room temperature for 2 h. After diluting the reaction solution with DCM, the reaction was quenched with sodium thiosulfate aqueous solution, extracted with DCM, the organic phase was collected, dried and concentrated, and purified by mixing (EA / PE = 1 / 4) to obtain a white solid product 73-4 (3.2 g, 49.0%).

[0246] (4) Under a nitrogen atmosphere, pinacol diborate (1.09 g, 4.32 mmol), potassium acetate (0.75 g, 7.2 mmol), and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride dichloromethane complex (0.15 g, 0.18 mmol) were added sequentially to 20 mL of a 1,4-dioxane solution containing substrate 73-4 (2 g, 3.6 mmol). The reaction was carried out at 100 °C for 3 h. The reaction mixture was used directly in the next step without any further treatment.

[0247] (5) After adding 2 mL of water to the reaction solution 73-5 from the previous step, cesium fluoride (1.09 g, 7.2 mmol), 2-chloro-5-(difluoromethoxy)pyrimidine (0.78 g, 4.32 mmol), and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride dichloromethane complex (0.15 g, 0.18 mmol) were added sequentially, and the reaction was carried out at 100 °C for 3 h. The reaction solution was filtered through diatomaceous earth, and the filtrate was evaporated to dryness to obtain the crude product. The crude product was purified by column chromatography (EA / PE = 1 / 1) to obtain the white solid product 73-6 (1.5 g, 68.2%).

[0248] (6) Dissolve substrate 73-6 (1.5 g, 2.4 mmol) in 20 mL of TFA and react at 60 °C for 8 h. The reaction solution was evaporated to dryness to obtain crude product, and crude product EA was slurried to obtain white solid product 70 (0.5 g, 41.6%).

[0249] (7) Dissolve substrate 70 (0.5 g, 1 mmol) in 5 mL DMSO, then add potassium carbonate (0.4 g, 3 mmol) and difluoroiodoethane (2.1 g, 10 mmol) sequentially, and react at 100 °C for 8 h. Pour the reaction solution into ice water and extract with EA. Wash the organic phase sequentially with 1 M dilute hydrochloric acid and saturated brine. Dry the organic phase, filter and concentrate. Purify the crude product by column chromatography (EA / PE = 1 / 4) to obtain a light yellow solid product 73 (0.2 g, 37.5%).

[0250] Bioactivity evaluation:

[0251] I. Insecticidal Activity Test of Compounds

[0252] The original drug was diluted with acetone and then prepared into gradient concentrations.

[0253] Fall armyworm, armyworm, and beet armyworm: Collect 3-4 leaves from host plants (young corn leaves) that have not been treated with pesticides and do not contain insect-resistant genes. Cut the leaves into 3-4 cm lengths and place them in a 9 cm outer diameter plastic box. Inoculate with 10 second-instar test insects that have been starved for 2 hours. Apply the pesticide using a spray tower. Repeat 3 times, using the highest dose containing acetone as a control. After application, tightly close the box lid and place it in a treatment room (temperature 25℃, humidity 60%). After 48 hours, investigate the number of dead insects and calculate the mortality rate. Mortality rate = (number of dead insects / number of test insects) × 100%

[0254] Brown planthoppers: Select brown planthoppers of uniform physiological condition raised indoors and place them in disposable transparent plastic cups. Inoculate each cup with 40-50 2nd-3rd instar planthoppers of similar growth. Place rice stalks in each cup, wrapping them with moist cotton balls to maintain humidity. Spray using a spray tower, and cover the cup opening after spraying. Repeat three times, using the highest dose of acetone as a control. After application, tightly seal the container and place it in a treatment room (temperature 25℃, humidity 60%). After 48 hours, count the number of dead planthoppers and calculate the mortality rate. Mortality rate = (number of dead planthoppers / number of planthoppers tested) × 100%

[0255] Table 2 Insecticidal activity test results

[0256] Note: N represents no data. Reference compound A: Reference compound B:

[0257] II. Insecticidal Activity Test of the Composition

[0258] 1) Testing Method

[0259] Component A is compound 1 in Table 1. Component B was purchased or obtained by conventional methods and diluted with acetone to prepare gradient concentrations.

[0260] The experimental methods for fall armyworm (3rd instar, 2DAA) and brown planthopper (3rd instar, 5DAA) are as described in Part I.

[0261] Peach aphid (mixed life stages): Radish plants were planted in disposable cups, 3-4 plants per cup. When the radish seedlings reached about 8cm in height, the aphids were introduced. After 3-4 days, once the aphid population reached a certain size, an experiment was conducted. A small spray bottle was used for spraying, spraying each plant 10-12 times until both sides of the leaves were moist but not dripping. The treatment was repeated 3 times, with the highest dose containing acetone serving as a control. After application, the plants were placed in a treatment room (temperature 25℃, humidity 60%). The number of dead aphids was counted after 48 hours, and the mortality rate was calculated. Mortality rate = (number of dead aphids / number of tested aphids) × 100%.

[0262] Peanut aphids (mixed life stages): Broad bean plants were planted in disposable cups, one plant per cup. When the seedlings reached approximately 10cm in height, the aphids were introduced. After 3-4 days, once the aphid population had reached a certain size, an experiment was conducted. A small spray bottle was used for spraying, applying 6-9 sprays per cup until both sides of the leaves were moist but not dripping. The treatment was repeated 3 times, using the highest dose containing acetone as a control. After application, the plants were placed in a treatment room (temperature 25℃, humidity 60%). The number of dead aphids was counted after 5 days, and the mortality rate was calculated. Mortality rate = (number of dead aphids / number of tested aphids) × 100%.

[0263] Yellow-striped flea beetles: Adult yellow-striped flea beetles of uniform physiological condition were selected and placed in disposable transparent plastic cups. Each cup contained 20 beetles of uniform growth. One to two leaves of a host plant (young radish leaves) that had not been treated with pesticides and did not contain insect-resistant genes were also placed in each cup. The mixture was then sprayed using a spray tower. After spraying, the cup opening was covered. This process was repeated three times, using the highest dose containing acetone as a control. After application, the cup was tightly sealed and placed in a treatment room (temperature 25℃, humidity 60%). The number of dead beetles was investigated after 48 hours, and the mortality rate was calculated. Mortality rate = (number of dead beetles / number of test beetles) × 100%.

[0264] 2) Qualitative evaluation of efficiency improvement

[0265] Toxicity was determined by setting different ratios within the selected range, and the optimal ratio was selected based on the synergistic effect. A synergistic effect > 0 indicates a synergistic effect; a synergistic effect close to 0 indicates an additive effect; and a synergistic effect < 0 indicates an antagonistic effect. Synergistic effect = Actual mortality rate - Theoretical mortality rate. Theoretical mortality rate = 1 - (1 - P1)(1 - P2)

[0266] In the formula, P1 and P2 represent the mortality rates of each individual dose in the mixture.

[0267] Table 3. Qualitative evaluation results of the composition synergistic effect

[0268] Furthermore, numerous tests have revealed that the compounds and their compositions described in this invention exhibit excellent control activity against many agricultural pests, including Lepidoptera (such as corn borers, rice stem borers, diamondback moths, beet armyworms, cotton bollworms, fall armyworms, and armyworms), Homoptera (such as cotton aphids, turnip aphids, pea aphids, peanut aphids, and green mirid bugs), Acari (such as two-spotted spider mites, truncated spider mites, and Turkestan spider mites), Diptera (such as leek leeks), Coleoptera (such as yellow flea beetles and small ape leaf beetles), and thrips (such as palm thrips, onion thrips, and tobacco thrips), as well as sanitary pests such as cockroaches (such as termites and cockroaches) and flies (such as flies and mosquitoes). These compounds not only possess broad-spectrum, high-efficiency, and systemic characteristics, but also effectively control resistant pests and have considerable commercial value.

Claims

1. A pyridyl-substituted imidazole ring compound, as shown in general formula I: wherein Q1, Q2 independently represent CH, C-halogen or N; X represents halogenoalkoxy; Y represents alkyl; R1 represents hydrogen, halogen, alkyl, alkenyl, ynyl, -OR9, -S(O). m R9 or said alkyl, alkenyl or alkynyl is optionally substituted by at least one group selected from halogen or -OR9; R2 represents hydrogen, alkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl or -alkylene-OR9; R8 represents hydrogen, alkyl or halogenoalkyl; R9 independently represents hydrogen, alkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, cycloalkyl or cycloalkylalkyl; m represents 0, 1 or 2; The foregoing "cycloalkyl", "heterocyclyl" or "aryl" is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, -OR 10 , -SR 10 , -(CO)R 10 , -(CO)OR 10 , -(SO)R 10 , or -(SO2)R 10 ; R 10 each independently represents hydrogen, alkyl, haloalkyl, phenyl or phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

2. A pyridyl substituted imidazo[1,2-a]pyrazine compound according to claim 1, wherein X represents C1-C8 halogenoalkoxy; Y represents C1-C8 alkyl; R1represents hydrogen, halogen, Ci-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, -OR9, -S(O)mR9or -S(O)mR9R9; m R9or said C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally substituted by at least one group selected from halogen or -OR9; R2 represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halogenoC1-C8 alkyl, halogenoC2-C8 alkenyl, halogenoC2-C8 alkynyl or -(C1-C8 alkylene)-OR9; R8 represents hydrogen, C1-C8 alkyl or halogenoC1-C8 alkyl; R9 independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halogenoC1-C8 alkyl, halogenoC2-C8 alkenyl, halogenoC2-C8 alkynyl, C3-C8 cycloalkyl or C3-C8 cycloalkylC1-C8 alkyl; The aforementioned "C3-C8cycloalkyl", "heterocyclyl" or "aryl" is optionally substituted with at least one radical selected from oxo, halogen, cyano, nitro, Ci-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, halogen-Ci-C8alkyl, halogen-C2-C8alkenyl, halogen-C2-C8alkynyl, -OR 10 , -SR 10 , -(CO)R 10 , -(CO)OR 10 , -(SO)R 10 or -(SO2)R 10 ; R 10 each independently represents hydrogen, C1-C8alkyl, haloC1-C8alkyl, phenyl or phenyl substituted by at least one radical selected from the group consisting of halogen, cyano, nitro, C1-C8alkyl, haloC1-C8alkyl, C1-C8alkyloxycarbonyl, C1-C8alkylthio, C1-C8alkylsulfonyl, C1-C8alkoxy or haloC1-C8alkoxy.

3. A pyridyl substituted imidazo[1,2-a]pyrazine compound according to claim 1 or 2, wherein X represents C1-C6 halogenoalkoxy; Y represents C1-C6 alkyl; R1represents hydrogen, halogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, -OR9, -S(O)mR9or -S(O)mR9R9; m R9or said C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally substituted by at least one group selected from halogen or -OR9; R2 represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogenoC1-C6 alkyl, halogenoC2-C6 alkenyl, halogenoC2-C6 alkynyl or -(C1-C6 alkylene)-OR9; R8 represents hydrogen, C1-C6 alkyl or halogenoC1-C6 alkyl; R9 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogenoC1-C6 alkyl, halogenoC2-C6 alkenyl, halogenoC2-C6 alkynyl, C3-C6 cycloalkyl or C3-C6 cycloalkylC1-C6 alkyl; The aforementioned "C3-C6cycloalkyl", "heterocyclyl" or "aryl" is optionally substituted with at least one radical selected from oxo, halogen, cyano, nitro, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, halogen-C1-C6alkyl, halogen-C2-C6alkenyl, halogen-C2-C6alkynyl, -OR 10 , -SR 10 , -(CO)R 10 , -(CO)OR 10 , -(SO)R 10 or -(SO2)R 10 . R 10 each independently represents hydrogen, C1-C6alkyl, haloC1-C6alkyl, phenyl or phenyl substituted by at least one radical selected from the group consisting of halogen, cyano, nitro, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkoxy or haloC1-C6alkoxy; Preferably, the compound is selected from any one of Table 1.

4. A method for preparing a pyridyl-substituted imidazole cyclic compound as described in any one of claims 1-3, characterized in that, comprising the following steps: obtaining compounds of general formula II and III by coupling reaction A compound as shown in general formula I, whose reaction equation is as follows: wherein Q1, Q2, X, Y, R1and R2are as defined in any one of claims 1 to 3, one of M1and M2is halogen and the other is or -B(OH)2; Preferably, the reaction is carried out in the presence of a base, a solvent and a catalyst; more preferably, the base is selected from at least one of an inorganic base or an organic base; the solvent is an organic solvent / water, the organic solvent is selected from at least one of an aromatic hydrocarbon, DMF, DMA, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate; the catalyst is selected from at least one of Pd(PPh3)4, Pd(dppf)Cl2, Pd(OAc)2, PdCl2(PPh3)2 or 1,1'-bis(diphenylphosphino) ferrocene palladium(II) dichloride dichloromethane complex; or either M1, M2is alkylthio and the other is or -B(OH)2; Preferably, the reaction is carried out in the presence of a solvent and a catalyst; more preferably, the solvent is selected from at least one of an aromatic hydrocarbon, dichloroethane, Dioxane or dichloromethane; the catalyst is a palladium reagent selected from at least one of Pd(PPh3)4, Pd(dppf)Cl2, Pd(dppf)Cl2.CH2Cl2, Pd(OAc)2, PdCl2(PPh3)2 or 1,1'-bis(diphenylphosphino) ferrocene palladium(II) dichloride dichloromethane complex and / or a copper reagent is copper(I) thiophene-2-carboxylate.

5. An insecticide composition, characterized by, comprising an insecticidally effective amount of at least one of the pyridyl-substituted imidazole ring compounds according to any one of claims 1 to 3; preferably, further comprising formulation adjuvants; more preferably, further comprising other active ingredients.

6. The composition of claim 5, wherein, The other active ingredients are selected from at least one of the following compounds: (1) acetylcholinesterase (AChE) inhibitors: acephate, chlorpyrifos; (2) sodium channel modulators: acrinathrin, bifenthrin, cyfluthrin; (3) competitive modulators of the nicotinic acetylcholine receptor (nAChR): (3) GABA-gated chloride channel antagonists: clothianidin, imidacloprid, thiamethoxam; (4) nicotinic acetylcholine receptor (nAChR) allosteric modulators: spinosad, spinetoram; (5) glutamate-gated chloride channel (GluCl) allosteric modulators: emamectin benzoate, abamectin; (6) uncouplers that affect oxidative phosphorylation by disrupting proton gradients: clofentezine; (7) nicotinic acetylcholine receptor (nAChR) channel blockers: spinetoram; (8) chitin biosynthesis inhibitors affecting chitin synthase 1: lufenuron; (9) ecdysone receptor agonists: methoxyfenozide; (10) voltage-dependent sodium channel blockers: indoxacarb; (11) ryanodine receptor modulators: chlorantraniliprole, cyantraniliprole; (12) Y-aminobutyric acid (GABA) gated chloride channel allosteric modulators: indoxacarb, metaflumizone, isocarbamid, clofentezine; (13) scolophony modulators - unknown target site: flonicamid; (14) Chordotonin TRPV channel modulators: pymetrozine, (15) chitin biosynthesis inhibitors (type 1): buprofezin; (16) acetylcholinesterase (AChE) inhibitors: malathion; (17) mitochondrial electron transport complex (I) inhibitors: pyridaben; (18) acetyl-CoA carboxylase inhibitors: spirotetramat; (19) Unknown mechanism of action:

7. A method for controlling pests, characterized by, comprising contacting the pest or its environment with a biologically effective amount of a pyridyl-substituted pyrimidinyl compound of any one of claims 1-3 or a composition of claim 5 or 6.

8. Use of a pyridyl-substituted pyrimidinyl compound of any one of claims 1-3 or a composition of claim 5 or 6 for controlling pests.

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