Substituted fused-imidazole ring compound, and preparation method therefor, insecticidal composition thereof and use thereof

Abstract

The present invention relates to the technical field of pesticides, and specifically relates to a substituted fused-imidazole ring compound, and a composition thereof and a use thereof. The compound is as shown in general formula I, wherein Q1 and Q2 each independently represent CH, C-halogen or N; X represents fluorine; Y represents alkyl; R1 represents hydrogen, halogen, alkyl, alkenyl or the like; and R2 represents hydrogen, alkyl, alkenyl, alkynyl or the like. The compound exhibits excellent control efficacy against pests such as Spodoptera frugiperda and Mythimna separata.

Description

Substituted pyrazole compounds, methods for preparing the same, insecticidal compositions and uses thereof TECHNICAL FIELD

[0001] The present application belongs to the technical field of pesticides, and particularly relates to a substituted pyrazole compound, a method for preparing the same, an insecticidal composition and uses thereof. BACKGROUND

[0002] In recent years, due to the long-term use of pest control agents such as insecticides or fungicides, pests have acquired resistance and become difficult to control by the existing insecticides or fungicides. In addition, some of the known pest control agents are highly toxic, or some destroy the ecological system through their long-term residual properties. In this case, although a large number of insecticides are known, there is still a need to develop new pest control agents with low toxicity and low residual properties. SUMMARY

[0003] The present application provides a substituted pyrazole compound, a method for preparing the same, an insecticidal composition and uses thereof, which has excellent insecticidal activity against Spodoptera littoralis, Mythimna separata and the like.

[0004] The technical solution adopted by the present application is as follows:

[0005] A substituted pyrazole compound, as shown in general formula I:

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

[0007] X represents fluorine;

[0008] Y represents alkyl;

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

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

[0011] R8 represents hydrogen, alkyl or haloalkyl;

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

[0013] m represents 0, 1 or 2;

[0014] The aforementioned "cycloalkyl", "heterocyclyl" or "aryl" is optionally substituted by 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 ;

[0015] R 10 each independently represents hydrogen, alkyl, haloalkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

[0016] Preferably, Y represents C1-C8alkyl;

[0017] R1represents hydrogen, halogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, -OR9, -S(O) m R9or said C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl is optionally substituted by at least one group selected from halogen or -OR9;

[0018] R2represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl or -(C1-C8alkylene)-OR9;

[0019] R8represents hydrogen, C1-C8alkyl or haloC1-C8alkyl;

[0020] R9each independently represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl, C3-C8cycloalkyl or C3-C8cycloalkylC1-C8alkyl;

[0021] The aforementioned "cycloalkyl", "heterocyclyl" or "aryl" is optionally substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl, -OR 10 , -SR 10 , -(CO)R 10 , -(CO)OR 10 , -(SO)R 10 or -(SO2)R10 substituted by at least one group selected from the group consisting of halogen, cyano, nitro, C1-C8alkyl, haloC1-C8alkyl, C1-C8alkoxycarbonyl, C1-C8alkylthio, C1-C8alkylsulfonyl, C1-C8alkoxy or haloC1-C8alkoxy;

[0022] R 10 each independently represents hydrogen, C1-C8alkyl, haloC1-C8alkyl, phenyl or phenyl substituted by at least one group selected from the group consisting of halogen, cyano, nitro, C1-C8alkyl, haloC1-C8alkyl, C1-C8alkoxycarbonyl, C1-C8alkylthio, C1-C8alkylsulfonyl, C1-C8alkoxy or haloC1-C8alkoxy.

[0023] More preferably, Y represents C1-C6alkyl;

[0024] R1represents hydrogen, halogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, -OR9, -S(O) m R9or said C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl is optionally substituted by at least one group selected from halogen or -OR9;

[0025] R2represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, haloC1-C6alkyl, haloC2-C6alkenyl, haloC2-C6alkynyl or -(C1-C6alkylene)-OR9;

[0026] R8represents hydrogen, C1-C6alkyl or haloC1-C6alkyl;

[0027] R9each independently represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, haloC1-C6alkyl, haloC2-C6alkenyl, haloC2-C6alkynyl, C3-C6cycloalkyl or C3-C6cycloalkylC1-C6alkyl;

[0028] the aforementioned "C3-C6cycloalkyl", "heterocyclyl" or "aryl" is optionally substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, haloC1-C6alkyl, haloC2-C6alkenyl, haloC2-C6alkynyl, -OR 10 , -SR 10 , -(CO)R 10 , -(CO)OR 10 , -(SO)R 10 or -(SO2)R 10 ;

[0029] R 10independently represent hydrogen, C1-C6alkyl, haloC1-C6alkyl, phenyl or phenyl substituted with at least one group selected from halo, cyano, nitro, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkyloxycarbonyl, C1-C6alkylsulfanyl, C1-C6alkylsulfonyl, C1-C6alkoxy or haloC1-C6alkoxy.

[0030] In one embodiment, R1represents haloC1-C6alkyl.

[0031] In the definitions of the compounds of the general formulae described above and in all the formulae below, the professional terms used, whether used alone or in a composite, represent the following substituents: alkyl groups having more than two carbon atoms can be straight-chained or branched. As in the composite "alkylene-OR9", alkylene can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. Alkyl groups are, for example, C1alkyl - methyl; C2alkyl - ethyl; C3alkyl - propyl, such as n-propyl or isopropyl; C4alkyl - butyl, such as n-butyl, isobutyl, tert-butyl or 2-butyl; C5alkyl - pentyl, such as n-pentyl; C6alkyl - hexyl, such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, alkenyl is, for example, ethenyl, 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 is, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. The multiple bonds can be in any position of each unsaturated group. Cycloalkyl is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl group having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, wherein the double bonds can be in any position. Halo is fluorine, chlorine, bromine or iodine.

[0032] Unless otherwise specified, "aryl" as used herein includes, but is not limited to, phenyl, naphthyl, " Heterocyclyl" as used herein includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups " Heterocyclyl" as used herein includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups

[0033] The term "optionally" or "optional" means that the subsequently described event or circumstance can or can not occur, and thus that the description includes instances where the event or circumstance occurs and instances where it does not. For example, the term "optionally substituted" means that the specified atom or group is either unsubstituted or substituted with one or more substituents. If a group is substituted with a group, this is to be understood to mean that the group is substituted with one or more groups, which are the same or different, selected from those mentioned. In addition, the same or different substituents contained in the same or different substituents are each independently selected, which can be the same or different. This also applies to ring systems formed from different atoms and units. At the same time, the scope of the claims is to exclude those compounds which are chemically unstable under standard conditions, as known to the person skilled in the art.

[0034] In addition, unless specifically limited otherwise, the term "substituted with at least one group" as used herein means substituted with, for example, 1, 2, 3, 4, or 5 groups; groups that are not labeled with a specific attachment position (including heterocyclyl, aryl, etc.) can be attached at any position, including the position attached to C or N; if it is substituted, the substituents can also be substituted at any position, as long as the rules of chemical bond connection are met. For example, a heteroaryl group substituted with 1 methyl group may represent etc.

[0035] If various functional groups are present, the present application also includes any keto and enol tautomer forms and mixtures and salts thereof.

[0036] The preparation method of the substituted imidazole ring compound includes the following steps:

[0037] The compounds shown in general formula II and III are prepared into the compound shown in general formula I through a coupling reaction, and the reaction equation is as follows:

[0038] wherein Q1, Q2, X, Y, R1 and R2 are as defined above, and either M1 or M2 is halogen, and the other is -B(OH)2 or

[0039] In a specific embodiment, the reaction is carried out in the presence of a base, a solvent and a catalyst.

[0040] In one embodiment, the base is at least one of an inorganic base (such as NaH, KH, NaOH, KOH, K2CO3, Na2CO3, Cs2CO3, KF, CsF, etc.) or an organic base (such as pyrazole, triethylamine, N,N diisopropylethylamine, pyridine, DIEA, potassium trimethylsilanolate, AcOK, AcONa, MeONa, EtONa, t-BuONa, t-BuOK, etc.).

[0041] In one embodiment, the solvent is an organic solvent / water, and the organic solvent is at least one of an aromatic hydrocarbon (such as benzene, chlorobenzene or toluene), DMF, DMA, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate.

[0042] In one embodiment, the catalyst is at least one of Pd(PPh3)4, Pd(dppf)Cl2, Pd(OAc)2, PdCl2(PPh3)2 or 1,1'-bis(diphenylphosphino)ferrocene palladium(II) dichloromethane complex.

[0043] In addition, the compound as shown in Formula I can be prepared according to the method shown in CN201780006638.8, CN202280017806.4, etc.

[0044] The present application also provides an intermediate, as shown in Formula II.

[0045] According to the present application, the salts of the compounds of the present application, such as the salts with bases or the acid addition salts, are all customary non-toxic salts, preferably the agriculturally and / or physiologically acceptable salts. Preference is given to the salts with inorganic bases, such as the alkali metal salts (for example sodium, potassium or cesium salts), the alkaline earth metal salts (for example calcium or magnesium salts), the ammonium salts; or the salts with organic bases, in particular with organic amines, such as the triethylammonium salts, the dicyclohexylammonium salts, the N,N'-dibenzylethylenediammonium salts, the pyridinium salts, the picolinium salts or the ethanolammonium salts; the salts with inorganic acids (for example the hydrochlorides, the hydrobromides, the dihydrogen sulfates, the trihydrogen phosphates or the phosphates); the salts with organic carboxylic acids or organic sulfonic acids (for example the formates, the acetates, the trifluoroacetates, the maleates, the tartrates, the methanesulfonates, the benzenesulfonates or the 4-toluenesulfonates). It is known that tertiary amines such as some of the compounds of the present application are capable of forming N-oxides, which are likewise salts of the present application.

[0046] Depending on the nature of the substituents, the compounds of the formula I can exist in the form of geometric and / or optically active isomers or in the form of corresponding isomer mixtures of different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The present application therefore includes pure stereoisomers as well as any mixtures of these isomers.

[0047] The present application also relates to a method for controlling animal pests, wherein the compounds of the formula I can act on the animal pests and / or their habitat. The control of the animal pests is preferably carried out in agriculture and forestry, and in the protection of materials. Excluded from the method are, preferably, methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods which are carried out on the human or animal body.

[0048] The present application also relates to the use of the compounds of the formula I as pesticides, in particular as crop protection agents.

[0049] In the context of the present application, the term "pesticide" also generally includes the term "crop protection agent".

[0050] Compounds of formula I having good plant tolerance, favourable homeotherm toxicity and good environmental compatibility are suitable for protecting plants and plant organs, for enhancing harvest yields, for improving the quality of the harvested material and for controlling animal pests, in particular insects, arachnids, Myriapods, Nematodes and Molluscs, that occur in agriculture, in horticulture, in livestock farming, in poultry farming, in fish farming, in forestry, in gardens and leisure facilities, in the protection of stored products and materials and in the hygiene sector. These compounds are preferably used as insecticides. They can be active against normally sensitive and resistant species and against all or some stages of development. The pests mentioned include, but are not limited to, pests from the phylum Arthropoda, in particular from the class Arachnida, from the class Chilopoda, from the class Collembola, from the class Diplopoda, from the class Insecta, from the order Coleoptera, from the order Diptera, from the order Heteroptera, from the order Homoptera, from the order Hymenoptera, from the order Isopoda, from the order Isoptera, from the order Lepidoptera, from the order Orthoptera or Saltatoria, from the order Phthiraptera, from the order Psocoptera, from the order Siphonaptera, from the order Thysanoptera, from the order Zygentoma (= Thysanura), from the class Symphyla, from the phylum Mollusca, and from the class Gastropoda.

[0051] At certain concentrations and application rates, the compounds of formula I can also optionally be used as insecticides, safeners, growth regulators or agents for improving plant properties, as fungicides and gametocides, for example as fungicides, antimycotics, bactericides, viricides (including antiviroid agents) or as agents against MLO (Mycoplasma-like organisms) and RLO (Rickettsiella-like organisms). If appropriate, they can also be used as intermediates or precursors for the synthesis of other active ingredients.

[0052] The present application also relates to formulations comprising at least one compound of the formula I and to the use thereof as a pesticidal application form, such as drenches, drip and spray liquids, prepared therefrom. In certain cases, the application forms comprise further pesticides and / or adjuvants having an improved action, such as penetrants, for example vegetable oils (such as rapeseed oil, sunflower oil), mineral oils (such as paraffin oil), alkyl esters of vegetable fatty acids (such as rapeseed oil methyl ester or soybean oil methyl ester), or alkanol alkoxylates; and / or spreaders, for example alkylsilicones and / or salts (such as organic or inorganic ammonium or phosphonium salts, for example ammonium sulfate or di-ammonium hydrogenphosphate); and / or retention promoters, for example dioctyl sulfosuccinate or hydroxypropyl guar polymer; and / or wetters, for example glycerol; and / or fertilizers, for example ammonium-, potassium- or phosphorus-containing fertilizers.

[0053] The formulations which are customary are, for example, water-soluble liquids (SL), emulsifiable concentrates (EC), aqueous emulsions (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS); these and other possible formulation types are described, for example, by Crop Life International in the following publication: Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, developed by the Joint FAO / WHO Committee on Pesticide Specifications, 2004, ISBN: 9251048576. The formulations optionally comprise, in addition to the compound(s) of the formula I, further agrochemically active ingredients.

[0054] These are preferably formulations or application forms which comprise auxiliaries, such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners; and or other auxiliaries, such as adjuvants. In the present context, an adjuvant is a component which enhances the biological efficacy of the formulation, whereas the component itself does not have any biological efficacy. Examples of adjuvants are agents which promote retention, spreading, adhesion to the leaf surface or penetration.

[0055] The formulations are prepared in known manner, for example by mixing the compound of the formula I with auxiliaries, such as extenders, solvents and / or solid carriers and / or further auxiliaries such as surfactants. The formulations are prepared immediately before use or during use.

[0056] The adjuvants used can be substances which are suitable for imparting particular properties to the formulations of the compounds of the formula I or to the use forms prepared from these formulations, such as ready-to-use insecticide sprays, such as spray liquors or seed dressing products, for example particular physical, technical and / or biological properties.

[0057] Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example selected from the group consisting of aromatic or aliphatic hydrocarbons, such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorbenzenes, alcohols and polyols which can also be optionally substituted, etherified and / or esterified, ketones, such as acetone, cyclohexanone, esters, including fatty and oil, and (poly)ethers, unsubsti- tuted and substituted amines, amides, lactams, such as N-alkylpyrrolidones, and lactones, sulfones and sulfoxides, such as dimethylsulfoxide.

[0058] If the extender used is water, it is also possible to use, for example, organic solvents as cosolvents. Useful liquid solvents are mainly: aromatic compounds, such as xylene, toluene or alkylnaphthalenes; chlorinated aromatic and aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or dichloromethane; aliphatic hydrocarbons, such as cyclohexane or paraffins, such as mineral oil fractions, mineral and vegetable oils; alcohols, such as butanol or glycol and ethers and esters thereof; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strongly polar solvents, such as dimethylformamide, dimethylacetamide and dimethylsulfoxide and water.

[0059] In principle, all suitable solvents can be used. Examples of suitable solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes; chlorinated aromatic or aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes, dichloromethane; aliphatic hydrocarbons, such as cyclohexane, paraffins, mineral oil fractions, mineral and vegetable oils; alcohols, such as methanol, ethanol, isopropanol, butanol or glycol and ethers and esters thereof; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strongly polar solvents, such as dimethylsulfoxide and water.

[0060] In principle, all suitable carriers can be used. Useful carriers include, inter alia, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth; and ground synthetic materials, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used. Useful carriers for granules include, for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite; and synthetic granules of inorganic and organic powders; and granules of organic materials such as sawdust, paper, coconut shells, corn cobs and tobacco stalks.

[0061] Also liquid gaseous extenders or solvents can be used. Particularly suitable extenders or carriers are those which are gaseous at ambient temperature and atmospheric pressure, for example aerosol propellant gases such as halogenated hydrocarbons, and also butane, propane, nitrogen and carbon dioxide.

[0062] Examples of emulsifiers and / or foaming, dispersing or wetting agents, or mixtures of these surfactants, having ionic or non-ionic properties, are salts of polyacrylic acids, salts of lignosulphonic acids, salts of phenolsulphonic acids or naphthalenesulphonic acids, polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty amines or substituted phenols, preferably alkylphenols or arylphenols, salts of sulphosuccinic esters, taurine derivatives, preferably alkyl taurates, phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of compounds containing sulphates, sulphonates and phosphates, such as alkyl aryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, protein hydrolysates, lignosulphite waste liquors and methylcellulose. If one of the above compounds of the formula I and / or one of the above inert carriers is not water-soluble and application is carried out in water, the presence of a surfactant is advantageous.

[0063] Other auxiliaries which can be present in the formulations and in the use forms derived from them include colourants such as inorganic pigments, for example iron oxide, titanium oxide, Prussian Blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and also nutrients and micronutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

[0064] The additional components can be stabilisers which improve chemical and / or physical stability, such as cold-stabilisers, preservatives, antioxidants, light stabilisers or other agents. Foaming and antifoaming agents can also be present.

[0065] Furthermore, the formulations and use forms derived from them can also comprise, as additional auxiliaries, sticking agents such as carboxymethylcellulose, and also natural and synthetic polymers in the form of powders, granules or latices, such as, for example, araboglucan, polyvinyl alcohol and polyacrylic acid, or natural phospholipids, such as cephalins, lecithins and synthetic phospholipids. Further possible auxiliaries are mineral and vegetable oils.

[0066] Optionally, other auxiliaries can be present in the formulations and in the use forms derived from them. Examples of such additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic agents, penetration agents, retention aids, stabilisers, sequestering and chelating agents, complexing agents, humectants and spreaders. In general, the compounds of the formula I can be combined with any solid or liquid additive which is customary for formulation purposes.

[0067] Useful retention promoters include all those substances which lower the kinetic surface tension, such as dioctyl sulfosuccinate; or all those substances which increase the viscoelasticity, such as hydroxypropyl guar polymers.

[0068] In the context of the present application, useful penetrants include all those substances which are typically used to enhance the penetration of active agrochemical ingredients into plants. In this context, penetrants are defined by their ability to penetrate the cuticle of the plant by the (usually aqueous) application liquid and / or by the spray coating, thereby increasing the mobility of the active ingredient in the cuticle. Examples include: alcohol alkoxylates, such as coconut fatty ethoxylate (10) or isotridecyl 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 phosphonium salts, such as ammonium sulfate or di-ammonium hydrogenphosphate.

[0069] The formulations preferably comprise from 0.00000001 to 98% by weight of the compound of formula I, more preferably from 0.01 to 95% by weight of the compound of formula I, most preferably from 0.5 to 90% by weight of the compound of formula I, based on the weight of the formulation.

[0070] The content of the compound of formula I in the use forms prepared from the formulations, especially the insecticides, can vary within wide ranges. The concentration of the compound of formula I in the use forms can generally be from 0.00000001 to 95% by weight of the compound of formula I, preferably from 0.00001 to 1% by weight, based on the weight of the use form. Application is carried out in the customary manner appropriate for the use form.

[0071] The compound of formula I can also be used in combination with one or more substances selected from the group consisting of suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbicides, beneficial organisms, pesticides, fertilizers, bird repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators, in order to broaden the spectrum of action, for example, to prolong the duration of action, to increase the rate of action, to prevent repellence or to prevent the development of resistance. In addition, such active ingredient combinations can improve plant growth and / or tolerance to abiotic factors, such as high or low temperatures, drought or high water content or soil salinity. It is also possible to improve flowering and fruiting performance, to optimize germination capacity and root development, to facilitate harvesting and to increase yield, to influence ripening, to improve the quality and / or nutritional value of the harvested products, to prolong the storage period and / or to improve the processing properties of the harvested products.

[0072] In addition, the compounds of the formula I can be present in mixtures with other active ingredients or semiochemicals such as attractants and / or bird repellents and / or plant activators and / or growth regulators and / or fertilizers. Likewise, the compounds of the formula I can be used in the form of mixtures with agents for improving the properties of plants such as growth, yield and quality of the harvested material.

[0073] In a particular embodiment of the present application, the compounds of the formula I are in the form of formulations or of use forms prepared from these formulations in mixture with other components, preferably those described below.

[0074] If one of the compounds mentioned below can exist in various tautomeric forms, these forms are included even if they are not explicitly mentioned in each case.

[0075] Insecticides / acaricides / nematicides

[0076] The active ingredients mentioned herein by their "common names" are known and are described, for example, in The Pesticide Manual, 16th Ed., British Crop Protection Council 2012, or can be retrieved on the internet (for example http: / / www.alanwood.net / pesticides). th

[0077] ​(1) acetylcholinesterase (AChE) inhibitors, such as carbamates, e.g. alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, e.g. azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, methacrifos, methidathion, naled, oxymetaxphos, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, prothoate, pyridafenthion, pyridaphore, quinalphos, sebufos, sulfotep, sulprofos, tebupirimiphos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion;malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.

[0078] (2) GABA-gated chloride ion channel antagonists, such as the cyclo- diene organochlorines, e.g. chlordane and endosulfan; or the phenylpyrazoles (fiproles), e.g. ethiprole and fipronil.

[0079] (3) Sodium channel modulators / voltage-dependent sodium channel blockers, for example pyrethroids, such as acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomers], deltamethrin, empenthrin [(EZ)-(1R) isomers], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(1R)-trans isomers], prallethrin [(2R)-cis / trans isomers], resmethrin, imiprothrin, frethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin (dimethyl-3, 7, 11-trimethyl-2, 4, 6-decadione), ZXI 1.1 (dimethyl-3, 7, 11- trimethyl-2, 4, 6-decanedione), and ZXI 1.2 (dimethyl-3, 7, 11-trimethyl-2, 4, 6- decanedione);[isomer]), prallethrin, pyrethrine, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)isomers], tralomethrin, and transfluthrin; or DDT; or methoxychloride.

[0080] (4) Nicotinic acetylcholine receptor (nAChR) agonists, such as neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor.

[0081] (5) Allosteric activators of nicotinic acetylcholine receptors (nAChR), such as spinosides, such as spintoram and spinosad.

[0082] (6) Chloride channel activators, such as abamectins / milbemycins, such as abamectin, emamectin benzoate, lepimectin and milbemectin.

[0083] (7) Juvenile hormone mimics, such as hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

[0084] (8) Active ingredients with unknown or non-specific mechanisms of action, such as

[0085] Alkyl halides, such as methyl bromide and other alkyl halides; or chloropicrine or thiocyanate or borax or tartar emetic.

[0086] (9) selective feeding blockers, such as pymetrozine or fionicamid.

[0087] (10) mite growth inhibitors, such as clofentezine, hexythiazox and diflovidazin or etoxazole.

[0088] (11) microbial disruptors of insect gut 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: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1.

[0089] (12) oxidative phosphorylation inhibitors, ATP disruptors, such as diafenthiuron or organotin compounds, such as azocyclotin, cyhexatin and fenbutatin oxide or propargite or tetradifon.

[0090] (13) oxidative phosphorylation decouplers interrupting the H+ gradient, such as chlorfenapyr, DNOC and sulfluramid.

[0091] (14) nicotinic acetylcholine receptor agonists, such as bensultap, cartap hydrochloride, thiocyclam and thiosultap-sodium.

[0092] (15) Inhibitors of chitin biosynthesis, type 0, for example bistrifluron, chlofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

[0093] (16) Inhibitors of chitin biosynthesis, type 1, for example buprofezin.

[0094] (17) Moulting disruptor (especially for Diptera, i.e. flies), for example cyromazine.

[0095] (18) Ecdysone receptor agonists, for example chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0096] (19) Octopaminergic agonists, for example amitraz.

[0097] (20) Complex-III electron transport inhibitors, for example hydramethylnone, or acequinocyl, or fluacrypyrim.

[0098] (21) Complex-I electron transport inhibitors, for example selected from METI acaricides, for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad; or rotenone (Derris spp.).

[0099] (22) Voltage-gated sodium channel blockers, for example indoxacarb or metaflumizone.

[0100] (23) Inhibitors of acetyl-CoA carboxylase, for example tetronic and tetramic acid derivatives, such as spirodiclofen, spiromesifen and spirotetramat.

[0101] (24) Complex-IV electron transport inhibitors, for example phosphines, such as aluminium phosphide, calcium phosphide, phosphine and zinc phosphide; or cyanides.

[0102] (25) Complex-II electron transport inhibitors, for example cyenopyrafen and cyflumetofen.

[0103] (28) Ryanodine receptor effectors, for example diamides, such as chlorantraniliprole, cyantraniliprole and flubendiamide;

[0104] other active ingredients, such as afidopyropen, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite, dicofol, diflovidazin, fluensulphone, flometoquin, flufenerim, flufenoxystrobin, flufiprole, fluopyram, flupyradifurone, fufenozide, heptafluthrin, imidaclothiz, iprodione, meperfluthrin, paichongding, pyflubumide, pyrifluquinazon, pyriminostrobin, tetramethylfluthrin and iodomethane, and agents based on Bacillus 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)-1 H-pyrazole-5-carboxamide (known from WO 2005 / 077934) and 1-{2-fluoro-4-methyl-5-[(2,2,2- trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1 H-1,2,4-triazol-5-amine (known from WO 2006 / 043635), {1 '-[(2E)-3-(4-chlorophenyl)prop-2-en-1 -yl]-5-fluorospiro[indole-3,4'- piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO 2003 / 106457), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4- (trifluoromethyl)phenyl]isonicotinamide (known from WO 2006 / 003494), 3-(2,5- dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2009 / 049851 ), 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-ene-4-yl carbonate (known from WO 2009 / 049851), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO 2004 / 099160), 4-(but-2-yn-1-yloxy)-6-(3-chlorophenyl)pyrimidine (known from WO 2003 / 076415), PF1364 (CAS Registry Number 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 WO 2005 / 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-naphthamide (known from WO 2009 / 002809), methyl 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylate (known from WO 2005 / 085216), methyl 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-ethylhydrazinecarboxylate (known from WO 2005 / 085216), methyl 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate (known from WO 2005 / 085216), methyl 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazinecarboxylate (known from WO 2005 / 085216), 1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide (known from WO 2010 / 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 CN 102057925), 3-chloro-N-(2-cyanopropan-2-yl)-N-[4-(1,1,1,2,3,3,3-Heptafluoroprop-2-yl)-2-methylphenyl] phtalamid (known from WO 2012 / 034472), 8-Chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (known from WO 2010 / 129500), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1 -oxathian-3-yl)benzamide (known from WO 2009 / 080250), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1 -oxathian-3-yl)benzamide (known from WO 2012 / 029672), 1 -[(2-chloro-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1 -ium-2-olate (known from WO 2009 / 099929), 1 -[(6-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1 -ium-2-olate (known from WO 2009 / 099929), (5S,8R)-1 -[(6-chloropyridin-3-yl)methyl]-9-nitro-2,3,5,6,7,8-hexahydro-1 H-5,8-epoxymidazo[1,2-a]azepine (known from WO 2010 / 069266), (2E)-1 -[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentylenehydrazinecarboximidamide (known from WO 2010 / 060231 ), 4-(3-{2,6-dichloro-4-[(3,3-dichloroprop-2-en-1 -yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluoromethyl)pyrimidine (known from CN 101 337 940), N-[2-(tert-butylcarbamoyl)-4-chloro-6-methylphenyl]-1 -(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide (known from WO 2008 / 134969),

[0105] Fungicides

[0106] The active ingredients identified herein by their common names are known and described, for example, in the "Pesticide Manual" or on the internet (e.g. http: / / www.alanwood.net / pesticides).

[0107] Biological pesticides as mixing partners

[0108] The compounds of formula I can be combined with biological pesticides.

[0109] Biological pesticides include, inter alia, bacteria, fungi, yeasts, plant extracts and products produced by microorganisms, including proteins and secondary metabolites.

[0110] Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria which act as bioinsecticides, fungicides or nematicides.

[0111] Also included are bacteria and fungi which are added to plants or plant parts or plant organs as "inoculants" and which promote plant growth and plant health by their special properties.

[0112] Safety agents as mixing partners

[0113] The compounds of the formula I can be combined with safeners, such as, for example, benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-{4-[(methylcarbamoyl)amino]phenyl} sulfamoyl)benzamide (CAS 129531-12-0), 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).

[0114] Plants and plant parts

[0115] All plants and plant parts can be treated in accordance with the application. Plants are to be understood as meaning all plants and plant populations such as wanted and unwanted wild plants or crop plants (including naturally occurring crop plants) such as cereals (wheat, rice, triticale, barley, rye, oats), maize, soya, potatoes, sugar beet, sugar cane, tomatoes, peas and other vegetable species, cotton, tobacco, rape and fruit plants (with the fruits mentioned: apples, pears, citrus fruits, and grapes). Crop plants can be plants which have been obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and plant cultivars which can be protected by the plant breeders' rights and which have been developed by plant breeding and selection or by biotechnological and genetic engineering methods. Plant parts are to be understood as meaning all parts and organs of the plants above and below ground such as shoot, leaf, flower and root, given as examples: leaves, needles, stems, trunks, flowers, fruit bodies, fruits and seeds, and also tubers. Plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.

[0116] The treatment of plants and plant parts with the compounds of the formula I according to the application is carried out directly or by allowing the compounds to act on the surroundings, habitat or storage space of the plants, by methods of treatment which are customary therefor, such as, for example, the dipping, spraying, vaporizing, fogging, spreading-on, painting-on, injection and, in the case of propagation material, especially seeds, the application of one or more coats.

[0117] As mentioned above, all plants and their parts can be treated in accordance with the application. In a preferred embodiment, wild plants species and plant cultivars, or those obtained by conventional biological breeding methods such as crossing or protoplast fusion, and their parts are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms), and their parts are treated. The term "parts" or "plant parts" or "plant parts" has been explained above. It is especially preferred to treat plants and plants parts of those plants which have been so far obtained by means of conventional breeding and propagation methods or those plants which are in the process of being developed therein. Plant cultivars are to be understood as meaning plants, which have given their properties with the aid of one or more genetic mutations or by means of a directed mutagenesis, a polyploidy, a coceptualization, a selection or a breeding, including plant cultivars which have been obtained by means of a biotechnological and genetic engineering method, such as gene technologically modified plants (genetically modified organisms).

[0118] Transgenic plants, seed treatment and inteeration events

[0119] 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.

[0120] Crop protection – types of treatment

[0121] The treatment of plants and plant parts with the compounds of the formula I is carried out directly by the customary treatment methods, for example by immersing, spraying, atomizing, irrigating, evaporating, dusting, fogging, spreading, foaming, painting, spreading on, watering (drenching), drip irrigation, in the case of propagation material, especially in the case of seeds, also by dry seed treatment, wet seed treatment, treatment of the slurry, encrusting, coating with one or more coats, etc. It is also possible to apply the compounds of the formula I using the ultra-low-volume process or to inject them into the soil in the form of their use forms or of the compounds of the formula I themselves.

[0122] A preferred direct treatment of plants is the foliar application, which means that the compounds of the formula I are applied to the leaves, wherein the frequency of treatment and the rate of application are to be adjusted to the infestation level of the pests.

[0123] In the case of systemically active compounds, the compounds of the formula I can also enter the plant via the root system. The plant is then treated by acting on the habitat of the plant with the compounds of the formula I. This can be done, for example, by drenching; or by mixing into the soil or the nutrient solution, which means that the plant site, for example the soil or a hydroponic system, is flooded with the compounds of the formula I in liquid form; or by soil application, which means that the compounds of the formula I are introduced into the plant site in solid form, for example in the form of granules. In the case of rice crops, this can also be done by metering the compounds of the formula I in solid application form, for example as granules, into the flooded rice field.

[0124] Seed treatment

[0125] The control of animal pests by treatment of plant seeds has long been known and is the subject of constant improvements. Seed treatment, however, involves a series of problems which cannot always be solved in a satisfactory manner. There is therefore a need to develop methods for protecting seeds and germinating plants which do not require or at least significantly reduce the additional application of pesticides during storage, after sowing or after the emergence of the plants. There is also a need to optimize the amount of active ingredient used in order to provide the seeds and germinating plants with the best possible protection against attack by animal pests, without the active ingredients used impairing the plants themselves. In particular, the methods used for seed treatment should also take into account the intrinsic pesticidal and / or nematicidal properties of pest-resistant or pest-tolerant transgenic plants in order to achieve the best possible protection of the seeds and germinating plants with the least possible use of crop protection products.

[0126] Thus, more particularly, the present application also relates to a method for protecting seed and germinating plants from attack by pests by treating the seed with one of the compounds of formula I. The method of the present application for protecting seed and germinating plants from attack by pests also comprises a method wherein the seed is treated simultaneously with one of the compounds of formula I and a mixture partner in one operation or successively. It also comprises a method wherein the seed is treated with one of the compounds of formula I and a mixture partner at different times.

[0127] The present application also relates to the use of the compounds of formula I for treating seed to protect the seed and resulting plants from attack by animal pests.

[0128] The present application further relates to seed which has been treated with one of the compounds of formula I to protect it from animal pests. The present application also relates to seed which has been treated simultaneously with one of the compounds of formula I and a mixture partner. The present application also relates to seed which has been treated with one of the compounds of formula I and a mixture partner at different times. In the case of seed which has been treated with one of the compounds of formula I and a mixture partner at different times, the individual components can be present in different layers of the seed. In this case, the layers comprising the compounds of formula I and the mixture partner can optionally be separated by intermediate layers. The present application also relates to seed, wherein one of the compounds of formula I and a mixture partner has been applied as part of a coating or other layer or in addition to a coating.

[0129] The present application also relates to seed which, after treatment with one of the compounds of formula I, is subjected to a film coating process to protect the seed from dust abrasion.

[0130] One of the advantages which exists when one of the compounds of formula I acts systemically is that the treatment of the seed protects not only the seed itself but also the plant which results from it (after emergence) from attack by animal pests. In this way, direct treatment of the crop at the time of sowing or shortly thereafter can be dispensed with.

[0131] A further advantage is that the treatment of seed with one of the compounds of formula I can promote the germination and emergence of the treated seed.

[0132] It is likewise considered advantageous that the compounds of formula I can also be used, inter alia, for transgenic seed.

[0133] The compounds of formula I can also be used in combination with signal technology components, as a result of which, for example, the colonization of symbionts, such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi, is improved and / or nitrogen fixation is optimized.

[0134] The compounds of the formula I are suitable for protecting the seed of any plant variety used in agriculture, in a greenhouse, in forestry or in horticulture. More particularly, the seed includes the seed of cereals (for example wheat, barley, rye, millet and oats), maize, cotton, soybeans, rice, potatoes, sunflowers, coffee beans, tobacco, oilseed rape, oilseed rape seeds, sugar beets (for example sugar beets and fodder beets), peanuts, vegetables (for example tomatoes, cucumbers, beans, cruciferous plants, onions, lettuce), fruit plants, turf plants and ornamental plants. Of particular importance is the treatment of the seed of cereals (wheat, barley, rye, oats), maize, soybeans, cotton, oilseed rape, oilseed rape seeds and rice.

[0135] As mentioned above, the treatment of transgenic seed with the compounds of the formula I is also of particular importance. The seed includes the seed of plants which usually comprise a heterologous gene which comprises the expression of at least one polypeptide which has, in particular, insecticidal and / or nematicidal properties. The heterologous gene in the transgenic seed can be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The compositions according to the application are particularly suitable for the treatment of transgenic seed which comprises at least one heterologous gene derived from Bacillus. The heterologous gene is more preferably derived from Bacillus thuringiensis.

[0136] In the context of the present application, the compounds of the formula I are applied to the seed. The seed is preferably treated in a state which is sufficiently stable so that no damage occurs during the treatment. In general, the seed can be treated at any point in time between harvesting and sowing. Seeds which have been separated from the plant and which have been freed from the husks, hulls, stems, skins, hairs or pulp are generally used. For example, seeds which have been harvested, cleaned and dried to a moisture content which allows storage can be used. Alternatively, seeds which have been dried, for example, and then treated with water and then dried again (for example, drenching) can also be used.

[0137] In general, when treating the seed, it must be ensured that the amount of the compound of the formula I and / or other additives applied to the seed is chosen so that the germination of the seed is not impaired and the plant which grows from the seed is not damaged. This must be ensured in particular in the case of active ingredients which can exhibit a phytotoxic effect at certain application rates.

[0138] The compounds of the formula I are generally applied to the seed in the form of suitable formulations. Suitable formulations and seed treatment methods are known to the person skilled in the art.

[0139] The compounds of the formula I can be converted into customary seed-dressing preparations, such as solutions, emulsions, suspensions, dusts, foams, slurries or other coating compositions for seeds, and also ULV formulations.

[0140] These formulations are prepared in known manner, by mixing the compounds of the formula I with customary additives, such as customary extenders and solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, foaming agents, preservatives, secondary thickeners, stickers, gibberellins and also water.

[0141] Useful colorants which can be present in the seed-dressing preparations used according to the application are all colorants which are customary for this purpose. It is possible to use sparingly water-soluble pigments or it is possible to use water-soluble dyes. Examples include the known colorants known as Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1.

[0142] Useful wetting agents which can be present in the seed-dressing preparations used according to the application are all substances which promote wetting and which are customary for the formulation of active agricultural-chemical ingredients. Preference is given to using alkyl naphthalene sulfonates, such as diisopropyl naphthalene sulfonate or diisobutyl naphthalene sulfonate.

[0143] Useful dispersants and / or emulsifiers which can be present in the seed-dressing preparations used according to the application are all non-ionic, anionic and cationic dispersants which are customary for the formulation of active agricultural-chemical ingredients. Preference is given to using non-ionic or anionic dispersants or mixtures of non-ionic or anionic dispersants. Suitable non-ionic dispersants include, in particular, ethylene oxide / propylene oxide block copolymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, and also phosphated or sulfated derivatives thereof. Suitable anionic dispersants are, inter alia, lignosulfonates, polyacrylic acid salts and condensates of arylsulfonic acids / formaldehyde.

[0144] Antifoams which can be present in the seed-dressing preparations used according to the application are all foam inhibitors which are customary for the formulation of active agricultural-chemical ingredients. Preference is given to using silicone antifoams and magnesium stearate.

[0145] Preservatives which can be present in the seed-dressing preparations used according to the application are all substances which can be used for this purpose in agrochemical compositions. Examples include dichlorophen and benzyl alcohol hemiformal.

[0146] Secondary thickeners which can be present in the seed-dressing preparations used according to the application are all substances which can be used for this purpose in active agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clays and finely divided silicas.

[0147] Useful binders which can be present in the seed dressing preparations used according to the application are all customary binders which can be used in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

[0148] Gibberellins which can be present in the seed dressing preparations used according to the application are preferably gibberellin A1, A3 (= gibberellic acid), A4 and A7, particularly preferred use being made of gibberellic acid.

[0149] The seed dressing preparations used according to the application can be used directly or after prior dilution with water to treat a large number of different kinds of seed. For example, the concentrated agents or the agents obtainable therefrom by dilution with water can be used to coat the seeds of cereals (such as wheat, barley, rye, oats and triticale), and also maize, rice, oilseed rape, peas, beans, cotton, sunflower, soybean and sugar beet, or a large number of different vegetable seeds. The seed dressing preparations used according to the application or their dilution forms used can also be used to dress the seeds of transgenic plants.

[0150] For the treatment of the seed with the seed dressing preparations used according to the application or the use forms prepared therefrom, all mixing apparatuses which are customary for seed dressing are available. More particularly, the process for seed dressing is as follows: the seeds are placed in batches or continuously in a mixer; the particular required amount of seed dressing preparation, either as such or after prior dilution with water, is added; and mixing is carried out until the preparation is uniformly distributed over the seeds. If appropriate, a drying operation can be carried out subsequently.

[0151] The application rates of the seed dressing preparations used according to the application can vary within a relatively wide range. They depend on the particular content of the compound of the formula I in the preparation and on the seed. The application rates of the compound of the formula I are generally from 0.001 g to 50 g per kg of seed; preferably from 0.01 g to 15 g per kg of seed.

[0152] For animal health

[0153] In the field of animal health, i.e. veterinary medicine, the active ingredients of the present application are used against animal parasites, especially ectoparasites or, in other embodiments, endoparasites. The term "endoparasites" includes, inter alia, helminths, such as tapeworms, roundworms or flukes; and protozoa, such as coccidia. Ectoparasites are generally and preferably arthropods, especially insects, such as biting and sucking flies, parasitic fly larvae, lice, hair lice, bird lice, fleas and the like; or mites, such as hard ticks or soft ticks; or mites, such as Demodex mites, autumn mites and bird mites and the like; and aquatic ectoparasites, such as copepods.

[0154] In the field of veterinary medicine, compounds of formula I which have a good homeotherm toxicity are suitable for controlling parasites which occur in animal breeding and animal keeping in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are effective against all or specific developmental stages of the parasites.

[0155] Agricultural livestock includes, for example, mammals such as sheep, goats, horses, donkeys, camels, water buffalo, rabbits, reindeer, fallow deer, and in particular cattle and swine; poultry such as turkeys, ducks, geese, and in particular chickens; fish and crustaceans, for example in aquaculture; and insects such as bees.

[0156] Domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, in particular dogs, cats, caged birds, reptiles, amphibians and ornamental fish.

[0157] In a preferred embodiment, the compounds of formula I are administered to mammals.

[0158] In another preferred embodiment, the compounds of formula I are administered to avians, i.e. caged birds and in particular poultry.

[0159] The use of the compounds of formula I to control animal parasites is intended to reduce or prevent the cases of disease, death and performance reduction (in the case of meat, milk, wool, rawhide, eggs, honey, etc.) so that animal keeping can be more economical and simple and better keeping of the animals in good condition is achieved.

[0160] In the field of animal health, the term "control" or "controlling" means that the compounds of formula I are effective in reducing the incidence of a particular parasite to a non-damaging extent in animals infected with such parasites. More specifically, in the present context, "control" means that the compounds of formula I are able to kill, inhibit the growth of or inhibit the multiplication of the respective parasites.

[0161] In general, the active ingredients of the present application can be used as such for treating animals. They are preferably used (administered) in the form of pharmaceutical compositions which can contain pharmaceutically acceptable excipients and / or adjuvants known in the art.

[0162] In the field of animal health and in animal husbandry, the active ingredients are used (administered) in the known manner, for example enterally, in the form of tablets, capsules, potions, drenches, granules, pastes, boluses, feed-through processes and suppositories; parenterally, for example by injection (intramuscularly, subcutaneously, intravenously, in particular intraperitoneally), by implantation; nasally; dermally, for example in the form of dips or baths, sprays, pour- ons and spot- ons, washes and dusts; and by means of mouldings comprising the active ingredients, for example collars, earmarks, tailmarks, limb bands, halters, marking devices and the like. The active ingredients can be formulated as shampoos or as suitable formulations which can be applied in the form of aerosols or non-pressurised spray agents such as pump sprays and atomised sprays.

[0163] In the case of use on livestock, poultry, domestic pets and the like, the active ingredients of the application can be used directly or after dilution (for example 100-fold to 10 000-fold dilution) in the form of formulations (for example dusts, wettable powders ["WP"], emulsions, emulsifiable concentrates ["EC"], flowable compositions, uniform solutions and suspensions ["SC"]) containing from 1% to 80% by weight of active ingredient, or they can be used as chemical baths.

[0164] In the case of use in the field of animal health, in order to broaden the activity spectrum, the active ingredients of the application can be used in combination with suitable synergists, repellents or other active ingredients, for example acaricides, insecticides, anthelmintics, antiprotozoans.

[0165] Vector control

[0166] The compounds of the formula I are also useful in vector control. In the context of the present application, a vector is an arthropod, in particular an insect or an arachnid, which is capable of transmitting a pathogen, for example a virus, a helminth, a unicellular organism and a bacterium, from a reservoir (plant, animal, human being or the like) to a host. The pathogen can be transmitted to the host mechanically (for example non-stinging flies with trachoma) or can be transmitted to the host after injection (for example malaria parasites of mosquitoes).

[0167] In the context of the present application, examples of vectors are insects, for example aphids, flies, leafhoppers or thrips, which can transmit plant viruses to plants. Other carriers capable of transmitting plant viruses are spider mites, lice, beetles and nematodes.

[0168] In the context of the present application, further examples of vectors are insects and arachnids, such as mosquitoes, especially mosquitoes of the genus Aedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria); and mosquitoes of the genus Culex, ticks, fleas, flies, mites and ticks, which can transmit pathogens to animals and / or humans.

[0169] If the compounds of the formula I are resistant to destruction, then vector control is also possible.

[0170] The compounds of the formula I are suitable for the protection of materials, especially natural materials, from the action of insects, for example from the attack or damage by insects from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.

[0171] Protection of industrial materials

[0172] The compounds of the formula I are suitable for protecting industrial materials from the attack or damage by insects, for example from the attack or damage by insects from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.

[0173] In the present context, industrial materials are to be understood as meaning inanimate materials, for example, preferably plastics, adhesives, sizes, paper and paperboard, leather, wood and processed wood products and coating compositions. Particularly preferred is the use of the application for the protection of wood.

[0174] In a further embodiment, the compounds of the formula I are used together with at least one further insecticide and / or at least one fungicide.

[0175] In a further embodiment, the compounds of the formula I are ready-to-use insecticides, meaning that they do not require further modification in order to be applied to the material. In particular, suitable further insecticides or fungicides are those mentioned above.

[0176] Surprisingly, it has also been found that the compounds of the formula I can be used for the protection of objects in contact with salt or brackish water from fouling, especially ship hulls, screens, nets, buildings, mooring equipment and signalling systems. It is likewise possible for the compounds of the formula I to be used as antifouling agents, either alone or in combination with other active ingredients.

[0177] Control of animal pests in the hygiene sector

[0178] The compounds of formula I are suitable for controlling animal pests in the hygiene sector. More particularly, the present application can be used in the domestic sector, in the hygiene sector and in the protection of stored products, in particular for controlling insects, arachnids and mites in closed spaces, for example dwellings, factory premises, offices, vehicle passenger compartments. For controlling animal pests, the compounds of formula I can be used alone or in combination with other active ingredients and / or auxiliaries. They are preferably used in insecticidal products for the domestic sector. The compounds of formula I are effective against sensitive and resistant species and against all stages of development.

[0179] These pests include, for example, pests from the classes of the Arachnida, Scorpiones, Araneae and Opiliones, the classes of the Chilopoda and Diplopoda, the order of the Blattaria, the orders of the Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Thysanura, the sub-class of the Malacostraca, the order of the Isopoda.

[0180] In bait or bait stations for spreading, the following forms are applied: aerosols, pressure- free spray products such as pump sprays and atomizer sprays, automatic aerosolizing systems, fogs, foams, gels, evaporative products with evaporator tablets made of cellulose or plastic, liquid evaporators, gel and film evaporators, propeller-driven evaporators, energy-free or passive evaporating systems, moth papers, moth bags and moth gels; as granules or dusts. DETAILED DESCRIPTION

[0181] The following examples are intended to illustrate the present application and should not be construed as limiting the application in any way. The scope of the application claimed is set forth in the claims.

[0182] In view of the economy and diversity of the compounds, we have preferably synthesized some compounds, among the synthesized compounds, some are listed in the following Table 1. The specific compound structure and the corresponding compound information are shown in Table 1. The compounds in Table 1 are only for better illustration of the present application, but do not limit the present application, and for those skilled in the art, this should not be understood as the scope of the above-mentioned subject matter of the present application is limited to the following compounds.

[0183] Table 1 Compound structure and its 1 H NMR

[0184] Several methods for preparing the compounds of the present application are illustrated in the following Schemes and Examples. Starting materials can be purchased from commercial suppliers or prepared by known literature methods or as otherwise described herein. Those skilled in the art will appreciate that other synthetic routes can be used to synthesize the compounds of the present application. Although specific starting materials and conditions are depicted in the following Schemes, other starting materials and conditions can readily be substituted. Modifications of the synthetic routes described below can be made and will be apparent to those skilled in the art, and such modifications are included within the scope of the present application. Further, the synthetic methods described below can be further modified in light of the disclosure herein, using conventional chemistry known to those of ordinary skill in the art. For example, appropriate protecting groups can be used during reactions, and the like.

[0185] The following method examples are provided to further illustrate the preparation of the compounds of the present application, and the specific materials, amounts and conditions are not intended to limit the scope of the application. The reagents used in the synthesis of the compounds described below can be purchased from commercial suppliers or readily prepared by one of ordinary skill in the art.

[0186] Representative compounds are prepared as follows, and other compounds are prepared in a similar manner.

[0187] 1. Synthesis of Compound 1

[0188] Compound 1-1 (300 mg, 0.6 mmol) was dissolved in 5.5 mL dioxane / H2O = 10 / 1, K2CO3 (250 mg, 1.8 mmol) and 2-bromo-5-fluoropyrimidine (158 mg, 0.9 mmol) were added. N2 was bubbled for 3 times, Pd(dppf)Cl2.CH2Cl2 (10 mg, 0.0012 mmol) was added, N2 was bubbled for 3 times again. The reaction was heated at 90 °C for 3 h. LCMS was used to monitor the reaction. The reaction was cooled to room temperature, silica gel powder was added, and the mixture was purified by normal phase to give Compound 1 (230 mg, 82%) as a yellow solid.

[0189] 2. Synthesis of Compound 8

[0190] (1) Dissolve 8-1 (0.35 g, 1.7 mmol) in dichloromethane (20 ml), add 8-2 (0.44 g, 1.7 mmol), drop in triethylamine (0.26 g, 2.5 mmol) and HATU (0.84 g, 2.2 mmol) in ice bath, warm to room temperature, react for 2 h. After the reaction is complete, wash with water, extract with dichloromethane, wash the organic phase with a semi-saturated sodium chloride solution, and concentrate to obtain crude 8-3, which is directly used in the next step.

[0191] (2) Dissolve crude 8-3 (0.5 g, 1.1 mmol) in HCOOH (50 ml), and warm to 120°C overnight. After the reaction is complete, cool the system to room temperature, concentrate to remove acetic acid, wash with water, extract with dichloromethane, wash the organic phase with a semi-saturated sodium chloride solution, and spin dry the organic phase fraction to obtain 8-4, which is directly used in the next step.

[0192] (3) Dissolve 8-4 (0.4 g, 0.92 mmol) in dichloromethane (30 ml), drop in metachloroperbenzoic acid (0.37 g, 1.85 mmol) in an ice bath, then react at room temperature for 1 h. After the reaction is complete, quench the reaction with a saturated sodium thiosulfate solution, wash with water, extract after neutralizing with a sodium bicarbonate solution, concentrate, add silica gel powder, and purify by normal phase to obtain 8-5 (0.35 g, 35% total yield from three steps, yellow solid).

[0193] (4) In a 100 ml single-neck flask, dissolve 8-5 (0.35 g, 0.75 mmol) in 20 ml of a 1,4-dioxane solution, add potassium acetate (0.22 g, 2.26 mmol) and pinacol diboronic acid (0.23 g, 0.9 mmol), replace with nitrogen three times, add Pd(dppf)Cl2.CH2Cl2(0.05 eq), replace with nitrogen three times again, react overnight at 90°C, and monitor for completion of the reaction. Cool the reaction liquid to room temperature, add silica gel powder, purify by normal phase, and spin dry the fraction to obtain 8-6 (120 mg, yield 31%, yellow solid).

[0194] (5) In a 100 ml single-neck flask, dissolve 8-6 (0.12 g, 0.23 mmol) in 20 ml of a 1,4-dioxane and water mixture solution (V 1,4-二氧六环 :V 水= 10: 1), potassium carbonate (0.1 g, 0.7 mmol) was added, nitrogen was replaced for three times, Pd(dppf)Cl2.CH2Cl2was added, nitrogen was replaced for three times again, 100 °C for 2 h, the reaction was monitored to be completed. The reaction solution was cooled to room temperature, silica gel powder was added, normal phase purification was performed, and the fractions were concentrated to give compound 8 (0.08 g, yield 71%, white solid).

[0195] 3. Synthesis of compound 24

[0196] Compound 1-1 (300 mg, 0.6 mmol) was dissolved in 5.5 mL dioxane / H2O = 10 / 1, K2CO3 (250 mg, 1.8 mmol) and 2-bromo-5-fluoropyridine (157 mg, 0.9 mmol) were added. Nitrogen was replaced for three times, Pd(dppf)Cl2.CH2Cl2(10 mg, 0.0012 mmol) was added, and nitrogen was replaced for three times again. 90 °C oil bath for 3 h. LCMS was used to monitor the reaction to be completed. The reaction solution was cooled to room temperature, silica gel powder was added, normal phase purification was performed, and compound 24 (230 mg, 82%) was obtained as a yellow solid.

[0197] Biological activity evaluation (insecticidal activity test)

[0198] Spodoptera exigua, Mythimna separata, Helicoverpa armigera, and Conogethes punctiferalis: The original drug was diluted with acetone to prepare a gradient concentration; 3-4 pieces of host plant leaves (young corn leaves) without insecticide and without insect-resistant genes were picked, cut into 3-4 cm long leaves, then placed in a 9 cm diameter plastic box, 10 2nd instar test insects treated by starvation for 2 h were introduced, and a spray tower was used for spraying. Repeat 3 times, use the highest dose containing acetone as a control, cover the box tightly after spraying, and place it in a treatment room (temperature 25 °C, humidity 60%). After 48 h, the number of dead insects was investigated, and the mortality rate was calculated. Mortality rate = (number of dead insects / number of test insects) x 100%

[0199] Nilaparvata lugens: Physiological state consistent Nilaparvata lugens were selected and placed in a disposable transparent plastic cup, 40-50 test insects growing consistently were introduced into each cup, and rice stems were placed in the cup. The rice stems were wrapped with wet cotton balls to maintain humidity, then a spray tower was used for spraying, and a cup cover was used to cover the cup after spraying. Repeat 3 times, use the highest dose containing acetone as a control, cover the box tightly after spraying, and place it in a treatment room (temperature 25 °C, humidity 60%). After 48 h, the number of dead insects was investigated, and the mortality rate was calculated. Mortality rate = (number of dead insects / number of test insects) x 100%

[0200] Rhopalosiphum padi: In a disposable small black bowl, 3-4 grains of wheat were planted in each cup, and the wheat seedlings were inoculated when they grew to about 10 cm. After 3-4 days, the test was carried out when the number of aphids reached a certain scale. A small spray bottle was used for spraying treatment, and each plant was sprayed (6-9) times, and the front and back of the leaves were wet but not liquid. Repeat 3 times, with the highest dose containing acetone as a control. After the application was completed, it was placed in a treatment room (temperature 25°C, humidity 60%). After 48 hours, the number of dead insects was investigated, and the mortality rate was calculated. Mortality rate = (number of dead insects / number of test insects) x 100%

[0201] Table 2 Insecticidal activity test results

[0202] Note: N represents no data. Control compound A: Control compound B:

[0203] At the same time, through many tests, it is found that the compounds and compositions described in the present application have good control activity on agricultural pests such as Lepidoptera (e.g. corn borer, diamondback moth, cabbage moth, beet armyworm, cotton bollworm, grass caterpillar, armyworm, etc.), Homoptera (e.g. cotton aphid, radish aphid, pea aphid, peanut aphid, green stink bug, etc.), Acarina (e.g. two-spotted spider mite, truncated spider mite, Turkey spider mite, etc.), Diptera (e.g. onion fly, etc.), Coleoptera (e.g. yellow curve jumping beetle, small ape leaf beetle, etc.), and Thysanoptera (e.g. palm thrips, onion thrips, tobacco thrips, etc.), as well as Blattidae (e.g. white ant, cockroach, etc.), Muscidae (e.g. fly, mosquito, etc.) and other health pests. Not only have the characteristics of broad-spectrum, high efficiency, strong systemicity, etc., but also can effectively control resistant pests, have certain commercial value.

Claims

1. A substituted tebuconazole cyclic compound, as shown in general formula I: wherein Q1, Q2 independently represent CH, C-halogen or N; X represents fluorine; 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, haloalkyl, haloalkenyl, haloalkynyl or -alkylene-OR9; R8 represents hydrogen, alkyl or haloalkyl; R9 independently represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, 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 substituted pyrazole compound according to claim 1, wherein 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, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl or -(C1-C8 alkylene)-OR9; R8 represents hydrogen, C1-C8 alkyl or haloC1-C8 alkyl; R9 independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, C3-C8 cycloalkyl or C3-C8 cycloalkylC1-C8 alkyl; The foregoing "C3-C8cycloalkyl", "heterocyclyl" or "aryl" is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-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 substituted pyrazole compound according to claim 1 or 2, wherein 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, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl or -(C1-C6 alkylene)-OR9; R8 represents hydrogen, C1-C6 alkyl or haloC1-C6 alkyl; R9 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-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 process for the preparation of substituted pyrazoimidazole ring compounds according to any one of claims 1 to 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 inorganic base or organic base; the solvent is organic solvent / water, the organic solvent is selected from at least one of 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) dichloromethane complex.

5. An insecticide composition, characterized by, comprising at least one of the substituted pyrimidinyl compounds of any one of claims 1-3 in a pesticidally effective amount; preferably, further comprising formulation adjuvants; more preferably, further comprising other active ingredients.

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

7. Use of the substituted pyrimidinyl compounds of any one of claims 1-3 or the composition of claim 5 in controlling pests.

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