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

Abstract

The present invention belongs to the technical field of pesticides, and specifically relates to a pyridyl-substituted heterocyclic compound and a preparation method therefor, an insecticidal composition and the use. The compound is represented by general Formula (I), wherein Q1represents NR7 or O; Q2 represents N, CH or C-halogen; X represents a cycloalkyl group, a cycloalkenyl group, an aryl group or a heterocyclic group; Y represents an alkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, etc.; R1 represents hydrogen, halogen, an alkyl group, an alkenyl group, etc.; R2 and R3 each independently represent hydrogen, halogen, a cyano group, etc.; and n represents 0, 1 or 2. The compound has a good control effect on fall armyworms, armyworms, etc.

Description

Pyridyl-substituted heterocyclic compound and preparation method, insecticidal composition and application thereof TECHNICAL FIELD

[0001] The present application belongs to the technical field of pesticides, and particularly relates to a pyridyl-substituted heterocyclic compound and a preparation method, an insecticidal composition and application thereof. BACKGROUND

[0002] In recent years, due to the long-term use of pest control agents such as insecticides or fungicides, pests have become resistant and difficult to control by the existing use of 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 pyridyl-substituted heterocyclic compound and a preparation method, an insecticidal composition and application 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 pyridyl-substituted heterocyclic compound, as shown in general formula I:

[0006] wherein Q1 represents NR7 or O;

[0007] Q2 represents N, CH or C-halogen;

[0008] X represents cycloalkyl, cycloalkenyl, aryl or heterocyclyl;

[0009] Y represents alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, -N(R9)2, cycloalkyl, cycloalkylalkyl, aryl, heterocyclyl, arylalkyl or heterocyclylalkyl;

[0010] R1 represents hydrogen, halogen, alkyl, alkenyl, alkynyl, -OR9, -S(O) m R9 or The alkyl, alkenyl or alkynyl is optionally substituted by at least one group selected from halogen or -OR9;

[0011] R2, R3 respectively independently represent hydrogen, halogen, cyano, alkyl, alkenyl, alkynyl, -N(R9)2, -OR9, -COOR9 or -S(O) m R9, the alkyl, alkenyl or alkynyl is optionally substituted by at least one group selected from halogen or -OR9;

[0012] R7represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl or -alkylene-OR9;

[0013] R8represents hydrogen, alkyl or haloalkyl;

[0014] R9represents independently for each occurrence hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl or cycloalkylalkyl;

[0015] n represents 0, 1 or 2;

[0016] m represents 0, 1 or 2;

[0017] The aforementioned "cycloalkyl", "cycloalkenyl", "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 , -(CO)N(R 10 )2, -(SO)R 10 or -(SO2)R 10 ;

[0018] R 10 represents independently for each occurrence 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.

[0019] Preferably, X represents C3-C8cycloalkyl, C3-C8cycloalkenyl, aryl or heterocyclyl;

[0020] Y represents C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl, -N(R9)2, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, aryl, heterocyclyl, arylC1-C8alkyl or heterocyclylC1-C8alkyl;

[0021] 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 with at least one group selected from halogen or -OR9;

[0022] R2, R3each independently represents hydrogen, halogen, cyano, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, -N(R9)2, -OR9, -COOR9or -S(O)mR9; m R9, said C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl is optionally substituted by at least one group selected from halogen or -OR9;

[0023] R7represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl or -(C1-C8alkylene)-OR9;

[0024] R8represents hydrogen, C1-C8alkyl or haloC1-C8alkyl;

[0025] R9each independently represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl, C3-C8cycloalkyl or C3-C8cycloalkylC1-C8alkyl;

[0026] n represents 0, 1 or 2;

[0027] m represents 0, 1 or 2;

[0028] The aforementioned "C3-C8cycloalkyl", "C3-C8cycloalkenyl", "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 , -(CO)N(R 10 )2, -(SO)R 10 or -(SO2)R 10 ;

[0029] R 10 each independently represents hydrogen, C1-C8alkyl, haloC1-C8alkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8alkyl, haloC1-C8alkyl, C1-C8alkoxycarbonyl, C1-C8alkylthio, C1-C8alkylsulfonyl, C1-C8alkoxy or haloC1-C8alkoxy.

[0030] More preferably, X represents C3-C6cycloalkyl, C3-C6cycloalkenyl, aryl or heterocyclyl;

[0031] Y represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, -N(R9)2, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, aryl, heterocyclyl, aryl C1-C6 alkyl or heterocyclyl C1-C6 alkyl;

[0032] R1 represents hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, -OR9, -S(O) m R9 or said C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally substituted with at least one group selected from halogen or -OR9;

[0033] R2, R3 each independently represents hydrogen, halogen, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, -N(R9)2, -OR9, -COOR9 or -S(O) m R9, said C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally substituted with at least one group selected from halogen or -OR9;

[0034] R7 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;

[0035] R8 represents hydrogen, C1-C6 alkyl or halo C1-C6 alkyl;

[0036] R9 each 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;

[0037] n represents 0, 1 or 2;

[0038] m represents 0, 1 or 2;

[0039] the aforementioned "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclyl" or "aryl" is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, -OR 10 , -SR 10 , -(CO)R 10 , -(CO)OR 10, - (CO)N (R 10 )2, - (SO)R 10 or - (SO2)R 10 substituted with at least one group selected from the group consisting of halogen, cyano, nitro, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkoxy or haloC1-C6alkoxy;

[0040] R 10 independently represent hydrogen, C1-C6alkyl, haloC1-C6alkyl, phenyl or phenyl substituted with at least one group selected from the group consisting of halogen, cyano, nitro, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkoxy or haloC1-C6alkoxy.

[0041] In the definition of the compounds of the general formulae described above and in all the structural 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-, and the like. 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. 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 bond can be in any position. Halogen is fluorine, chlorine, bromine or iodine.

[0042] Unless otherwise specified, the term "aryl" as used herein includes, but is not limited to, phenyl, naphthyl, The term "heterocyclyl" as used herein includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups and the like, including but not limited to heteroaryl, i.e., aromatic ring-like groups containing, for example, 3 to 6 ring atoms, 1 to 4 (e.g., 1, 2, 3, or 4) of the ring atoms being heteroatoms selected from oxygen, nitrogen, and sulfur, and optionally having a benzo ring fused thereto, for example

[0043] The term "optionally" or "optional" means that the subsequently described event or circumstance can or can not occur, and 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 designated atom or group is unsubstituted or substituted with one or more substituents. If a group is substituted with a group, this is understood to mean that the group is substituted with one or more groups, which are the same or different, selected from those mentioned. Additionally, the same or different substituents contained in the same or different substituents are each independently selected, which can be the same or different. This applies equally 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.

[0044] 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 position of attachment (including heterocyclyl, aryl, and the like) can be attached at any position, including the position of attachment to C or N; and if it is substituted, the substituents can also be substituted at any position, as long as the rules of chemical bonding are followed. For example, a heteroaryl group substituted with 1 methyl group may represent and the like.

[0045] If various functional groups are present, the present application also includes any keto and enol tautomeric forms and mixtures and salts thereof.

[0046] The preparation method of the pyridyl-substituted heterocyclic compound is prepared by the following steps:

[0047] The compound represented by general formula II and III is subjected to a coupling reaction to prepare the compound represented by general formula I, and the reaction equation is as follows:

[0048] wherein Q1, Q2, X, Y, R1, R2, R3, and n are as defined above, either M1 or M2 is halogen, and the other is or -B(OH)2.

[0049] In a specific embodiment, the reaction is carried out in the presence of a base, a solvent, and a catalyst.

[0050] 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.).

[0051] 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.

[0052] 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.

[0053] In addition, the compound of Formula I can be prepared according to the method described in CN201780006638.8, CN202280017806.4, etc.

[0054] The present application also provides an intermediate, as shown in Formula II.

[0055] 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 salts which are agriculturally and / or physiologically acceptable. 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'-dibenzylethylene-diammonium salts, the pyridinium salts, the picolinium salts or the ethanolammonium salts; the salts with inorganic acids (for example the hydrochlorides, the hydrobromides, the dihydrogen sulphates, the trihydrogen phosphates or the phosphates); the salts with organic carboxylic acids or organic sulphonic acids (for example the formates, the acetates, the trifluoroacetates, the maleates, the tartrates, the methanesulphonates, the benzenesulphonates or the 4-toluenesulphonates). 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.

[0056] 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 composition. 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.

[0057] 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.

[0058] The present application also relates to the use of the compounds of the formula I as pesticides, in particular as crop protection agents.

[0059] In the context of the present application, the term "pesticide" also generally includes the term "crop protection agent".

[0060] 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.

[0061] 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 (Rickettsiaceae-like organisms). If appropriate, they can also be used as intermediates or precursors for the synthesis of other active ingredients.

[0062] 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.

[0063] 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.

[0064] 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 further 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.

[0065] 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.

[0066] The adjuvants used can be substances suitable for imparting specific 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 insecticides, such as spray liquors or seed dressing products, for example specific physical, technical and / or biological properties.

[0067] 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, chlorobenzenes, 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 dimethyl sulfoxide.

[0068] 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 dimethyl sulfoxide and water.

[0069] 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 dimethyl sulfoxide and water.

[0070] 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 diatomite; 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 stems.

[0071] 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.

[0072] 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, for example 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.

[0073] 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.

[0074] The additional components can be stabilisers which improve chemical and / or physical stability, for example cold-stabilisers, preservatives, antioxidants, light stabilisers or other agents. Foaming and de-foaming agents can also be present.

[0075] 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 gum arabic, polyvinyl alcohol and polyacrylic acid, or natural phospholipids, such as cephalins, lecithins and synthetic phospholipids. Further possible auxiliaries are mineral and vegetable oils.

[0076] 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.

[0077] 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.

[0078] 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.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] 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.

[0084] 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.

[0085] Insecticides / acaricides / nematicides

[0086] The active ingredients mentioned herein by their "common names" are known and are described, for example, in The Pesticide Manual, 16thEd., British Crop Protection Council 2012, or can be retrieved on the internet (for example http: / / www.alanwood.net / pesticides). th ed., British Crop Protection Council 2012, or can be retrieved on the internet (for example http: / / www.alanwood.net / pesticides).

[0087] (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.

[0088] (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.

[0089] (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);pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) isomers], tralomethrin and transfluthrin; or DDT; or methoxychlor.

[0090] (4) agonists of the nicotinic acetylcholine receptor (nAChR), such as neonicotinoids, for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor.

[0091] (5) allosteric activators of the nicotinic acetylcholine receptor (nAChR), such as spinosyns, for example spinetoram and spinosad.

[0092] (6) chloride channel activators, for example, avermectins / milbemycins, such as abamectin, emamectin benzoate, lepimectin and milbemectin.

[0093] (7) juvenile hormone mimics, for example, juvenile hormone analogs such as hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

[0094] (8) active ingredients with unknown or unspecific mode of action, for example

[0095] alkyl halides, such as methyl bromide and other alkyl halides; or chloropicrine or sulfuryl fluoride or borax or tartar emetic.

[0096] (9) selective feeding blockers, such as pymetrozine or fionicamid.

[0097] (10) mite growth inhibitors, such as clofentezine, hexythiazox and diflovidazin or etoxazole.

[0098] (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.

[0099] (12) oxidative phosphorylation inhibitors, ATP disruptors, such as diafenthiuron or organotin compounds, such as azocyclotin, cyhexatin and fenbutatin oxide or propargite or tetradifon.

[0100] (13) oxidative phosphorylation decouplers interrupting the H+ gradient, such as chlorfenapyr, DNOC and sulfluramid.

[0101] (14) nicotinic acetylcholine receptor agonists, such as bensultap, cartap hydrochloride, thiocyclam and thiosultap-sodium.

[0102] (15) Inhibitors of chitin biosynthesis, type 0, for example bistrifluron, chlofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

[0103] (16) Inhibitors of chitin biosynthesis, type 1, for example buprofezin.

[0104] (17) Moulting disruptor (especially for Diptera, i.e. flies), for example cyromazine.

[0105] (18) Ecdysone receptor agonists, for example chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0106] (19) Octopaminergic agonists, for example amitraz.

[0107] (20) Complex-III electron transport inhibitors, for example hydramethylnone, or acequinocyl, or fluacrypyrim.

[0108] (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.).

[0109] (22) Voltage-gated sodium channel blockers, for example indoxacarb or metaflumizone.

[0110] (23) Inhibitors of acetyl-CoA carboxylase, for example tetronic and tetramic acid derivatives, such as spirodiclofen, spiromesifen and spirotetramat.

[0111] (24) Complex-IV electron transport inhibitors, for example phosphines, such as aluminium phosphide, calcium phosphide, phosphine and zinc phosphide; or cyanides.

[0112] (25) Complex-II electron transport inhibitors, for example cyenopyrafen and cyflumetofen.

[0113] (28) Ryanodine receptor effectors, for example diamides, such as chlorantraniliprole, cyantraniliprole and flubendiamide;

[0114] 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),

[0115] Fungicides

[0116] 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).

[0117] Biological pesticides as mixing partners

[0118] The compounds of formula I can be combined with biological pesticides.

[0119] Biological pesticides include, inter alia, bacteria, fungi, yeasts, plant extracts and products produced by microorganisms, including proteins and secondary metabolites.

[0120] Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria which act as bioinsecticides, fungicides or nematicides.

[0121] 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.

[0122] Safety agents as mixing partners

[0123] 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).

[0124] Plants and plant parts

[0125] 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.

[0126] 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.

[0127] 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).

[0128] Transgenic plants, seed treatment and inteeration events

[0129] 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.

[0130] Crop protection – types of treatment

[0131] 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.

[0132] 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.

[0133] 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.

[0134] Seed treatment

[0135] 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, methods 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.

[0136] 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.

[0137] 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.

[0138] 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.

[0139] 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.

[0140] 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.

[0141] A further advantage is that treatment of the seed with one of the compounds of formula I can promote germination and emergence of the treated seed.

[0142] It is likewise considered advantageous that the compounds of formula I can also be used, inter alia, for transgenic seed.

[0143] 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.

[0144] 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 seeds include the seeds 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 seeds of cereals (wheat, barley, rye, oats), maize, soybeans, cotton, oilseed rape, oilseed rape seeds and rice.

[0145] As mentioned above, the treatment of transgenic seeds with the compounds of the formula I is also of particular importance. The seeds include the seeds 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 seeds 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 seeds which comprise at least one heterologous gene derived from Bacillus. The heterologous gene is more preferably derived from Bacillus thuringiensis.

[0146] In the context of the present application, the compounds of the formula I are applied to the seeds. The seeds are preferably treated in a state which is sufficiently stable so that no damage occurs during the treatment. In general, the seeds can be treated at any point in time between harvesting and sowing. Seeds which have been separated from the plants 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.

[0147] In general, when treating the seeds, it must be ensured that the amount of the compounds of the formula I and / or other additives which are applied to the seeds is chosen so that the germination of the seeds is not impaired and the plants which grow from the seeds are not damaged. This must be ensured in particular in the case of active ingredients which can exhibit phytotoxic effects at certain application rates.

[0148] The compounds of the formula I are generally applied to the seeds in the form of suitable formulations. Suitable formulations and seed treatment methods are known to the person skilled in the art.

[0149] 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.

[0150] 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.

[0151] 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.

[0152] 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.

[0153] 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.

[0154] 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.

[0155] 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.

[0156] 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.

[0157] 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.

[0158] 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.

[0159] 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.

[0160] 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.

[0161] 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.

[0162] For animal health

[0163] 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.

[0164] 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.

[0165] 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.

[0166] 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.

[0167] In a preferred embodiment, the compound of Formula I is administered to a mammal.

[0168] In another preferred embodiment, the compound of formula I is administered to poultry, i.e., caged birds and especially poultry.

[0169] 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.

[0170] 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.

[0171] 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.

[0172] 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.

[0173] 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.

[0174] 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.

[0175] Vector control

[0176] 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).

[0177] 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.

[0178] 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.

[0179] If the compound of formula I is resistant to damage, then vector control is also possible.

[0180] 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.

[0181] Protection of industrial materials

[0182] 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.

[0183] 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.

[0184] In another embodiment, the compound of formula I is used in conjunction with at least one other insecticide and / or at least one fungicide.

[0185] 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.

[0186] 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.

[0187] Control of animal pests in the health field

[0188] 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.

[0189] 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.

[0190] 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

[0191] 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.

[0192] 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.

[0193] Table 1. Compound structures and their properties 1 H NMR

[0194] 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.

[0195] 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.

[0196] Examples of representative compounds are given below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0197] 1. Synthesis of Compound 9

[0198] 9-1 (3 g, 6.4 mmol) was dissolved in 50 mL of 1,4-dioxane, followed by the addition of 9-2 (2.5 g, 12.8 mmol) and cesium fluoride (1.9 g, 12.8 mmol), 5 mL of H₂O, and nitrogen purging. A catalytic amount of 1,1'-bis(diphenylphosphine)ferrocene palladium(II) dichloromethane complex was then added, and the temperature was slowly raised to 100 °C. The reaction was carried out for 12 h, and 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 passed through a column, and the fraction was evaporated to dryness to give 1.2 g of compound 9 (40% yield) as a white solid.

[0199] 2. Synthesis of Compound 10

[0200] 10⁻¹ (3 g, 6.2 mmol) was dissolved in 50 mL of 1,4-dioxane, followed by the addition of 9⁻² (2.4 g, 12.4 mmol) and cesium fluoride (1.9 g, 12.4 mmol), 5 mL of H₂O, and nitrogen purging. A catalytic amount of 1,1'-bis(diphenylphosphine)ferrocene palladium(II) dichloromethane complex was then added, and the temperature was slowly raised to 100 °C. The reaction was carried out for 12 h, and 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 1.3 g of compound 10 (yield 44.8%) as a white solid.

[0201] 3. Synthesis of Compound 11

[0202] 11-1 (3 g, 6 mmol) was dissolved in 50 mL of 1,4-dioxane, followed by the addition of 9-2 (2.3 g, 12 mmol) and cesium fluoride (1.8 g, 12 mmol), and 5 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 1.1 g of compound 11 (yield 41.2%) as a white solid.

[0203] 4. Synthesis of Compound 44

[0204] 44-1 (447 mg, 1 mmol) was dissolved in 20 mL of 1,4-dioxane, followed by the addition of 9-2 (0.39 g, 2 mmol) and cesium fluoride (0.3 g, 2 mmol), and 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 obtain 0.2 g of 44-1 (yield 45.9%) as a white solid.

[0205] 5. Synthesis of Compound 48

[0206] 48-1 (448 mg, 1 mmol) was dissolved in 20 mL of 1,4-dioxane, followed by the addition of 9-2 (0.39 g, 2 mmol) and cesium fluoride (0.3 g, 2 mmol), and 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 obtain 213 mg of 48-1 (yield 48.9%) as a white solid.

[0207] Bioactivity evaluation (insecticide activity test)

[0208] Fall armyworm, armyworm, beet armyworm, and peach fruit borer: The technical grade pesticide was diluted with acetone to prepare gradient concentrations. Leaves (young corn leaves) of 3-4 leaves from untreated host plants (not containing insect-resistant genes) were collected, cut into 3-4 cm lengths, and placed in a 9 cm diameter plastic box. Ten second-instar test insects, starved for 2 hours, were introduced into the box. The pesticide was applied using a spray tower. The treatment was repeated three times, with the highest dose containing acetone serving as a control. After application, the box was tightly sealed and placed in a treatment room (temperature 25℃, humidity 60%). The number of dead insects was assessed after 48 hours, and the mortality rate was calculated. Mortality rate = (number of dead insects / number of test insects) × 100%

[0209] Table 2 Insecticidal activity test results

[0210] Note: N represents no data; control compound A:

[0211] 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 heterocyclic compound, as shown in general formula I: wherein Q1represents NR7or O; Q2represents N, CH or C-halogen; X represents C3-C8cycloalkyl, C3-C8cycloalkenyl, aryl or heterocyclyl; Y represents C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl, -N(R9)2, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, aryl, heterocyclyl, arylC1-C8alkyl or heterocyclylC1-C8alkyl; R1 represents hydrogen, halogen, alkyl, alkenyl, ynyl, -OR9, -S(O). m R9 or said C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl is optionally substituted by at least one group selected from halogen or -OR9; R2 and R3 independently represent hydrogen, halogen, cyano, alkyl, alkenyl, ynyl, -N(R9)2, -OR9, -COOR9, or -S(O), respectively. m R9, wherein the alkyl, alkenyl or alkynyl group is optionally replaced by at least one group selected from halogens or -OR9; R7represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl or -(C1-C8alkylene)-OR9; R8represents hydrogen, C1-C8alkyl or haloC1-C8alkyl; R9independently of one another represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl, C3-C8cycloalkyl or C3-C8cycloalkylC1-C8alkyl; n represents 0, 1 or 2; m represents 0, 1 or 2; The foregoing "cycloalkyl", "cycloalkenyl", "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 , -(CO)N(R 10 )2, -(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. The pyridyl-substituted heterocyclic compound according to claim 1, characterized in that X represents C3-C8cycloalkyl, C3-C8cycloalkenyl, aryl or heterocyclyl; Y represents C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl, -N(R9)2, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, aryl, heterocyclyl, arylC1-C8alkyl or heterocyclylC1-C8alkyl; R1represents hydrogen, halogen, Ci-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, -OR9, -S(O)mR9or -S(O)mR9R9; m R9or said C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl is optionally substituted by at least one group selected from halogen or -OR9; R2, R3independently represent hydrogen, halogen, cyano, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, -N(R9)2, -OR9, -COOR9or -S(O)mR9; m R9, said C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl being optionally substituted by at least one group selected from halogen or -OR9; R7represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl or -(C1-C8alkylene)-OR9; R8represents hydrogen, C1-C8alkyl or haloC1-C8alkyl; R9independently of one another represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl, C3-C8cycloalkyl or C3-C8cycloalkylC1-C8alkyl; n represents 0, 1 or 2; m represents 0, 1 or 2; The aforementioned "C3-C8cycloalkyl", "C3-C8cycloalkenyl", "heterocyclyl" or "aryl" is optionally substituted with at least one radical selected from the group consisting of 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 , -(CO)N(R 10 )2, -(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. The pyridyl-substituted heterocyclic compound according to claim 1 or 2, characterized in that X represents C3-C6cycloalkyl, C3-C6cycloalkenyl, aryl or heterocyclyl; Y represents C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, haloC1-C6alkyl, haloC2-C6alkenyl, haloC2-C6alkynyl, -N(R9)2, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, aryl, heterocyclyl, arylC1-C6alkyl or heterocyclylC1-C6alkyl; R1represents hydrogen, halogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, -OR9, -S(O)mR9or -S(O)mR9R9; m R9or said C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl is optionally substituted by at least one group selected from halogen or -OR9; R2, R3independently represent hydrogen, halogen, cyano, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, -N(R9)2, -OR9, -COOR9or -S(O)mR9; m R9, said C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl being optionally substituted by at least one group selected from halogen or -OR9; R7represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, haloC1-C6alkyl, haloC2-C6alkenyl, haloC2-C6alkynyl or -(C1-C6alkylene)-OR9; R8represents hydrogen, C1-C6alkyl or haloC1-C6alkyl; R9independently of one another represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, haloC1-C6alkyl, haloC2-C6alkenyl, haloC2-C6alkynyl, C3-C6cycloalkyl or C3-C6cycloalkylC1-C6alkyl; n represents 0, 1 or 2; m represents 0, 1 or 2; The aforementioned "C3-C6cycloalkyl", "C3-C6cycloalkenyl", "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, halogenated C1-C6alkyl, halogenated C2-C6alkenyl, halogenated C2-C6alkynyl, -OR 10 , -SR 10 , -(CO)R 10 , -(CO)OR 10 , -(CO)N(R 10 )2, -(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 a pyridyl substituted heterocyclic compound according to any one of claims 1 to 3, characterized in that, comprising the following steps: Compounds of general formula II and III are prepared by coupling reaction A compound as shown in general formula I, whose reaction equation is as follows: wherein Q1, Q2, X, Y, R1, R2, R3 and n are as defined in any one of claims 1 to 3, and either M1 or M2 is halogen, the other being 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)2or 1,1'-bis(diphenylphosphino)ferrocene palladium(II) dichloride dichloromethane complex.

5. An insecticide composition, characterized by, comprising a pesticidally effective amount of at least one of the pyridyl substituted heterocyclic compounds of any one of claims 1 to 3; 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 pyridyl substituted heterocyclic compounds of any one of claims 1 to 3 or the composition of claim 5.

7. Use of the pyridyl substituted heterocyclic compounds of any one of claims 1 to 3 or the composition of claim 5 for controlling pests.

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