Fused heterocyclic compound and preparation method therefor, insecticidal composition and use thereof

Abstract

The present invention belongs to the technical field of pesticides, and specifically relates to a fused heterocyclic compound and a preparation method therefor, an insecticidal composition and the use thereof. The compound is represented by general formula I, wherein X represents cycloalkyl, aryl or heterocyclyl; R1, R2, R3, R4 and R5 each independently represent hydrogen, halogen, alkyl, alkenyl, etc.; and the compound exhibits an excellent prevention and control effect on Spodoptera frugiperda, Mythimna separata, Spodoptera litura, etc.

Description

Fused heterocyclic compound, preparation method thereof, insecticidal composition and use thereof TECHNICAL FIELD

[0001] The present application belongs to the technical field of pesticides, and particularly relates to a fused heterocyclic compound, a preparation method thereof, an insecticidal composition and use 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 fused heterocyclic compound, a preparation method thereof, an insecticidal composition and use thereof, which has excellent insecticidal activity against Spodoptera exigua, Mythimna separata, Spodoptera litura and the like.

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

[0005] A fused heterocyclic compound, as shown in general formula I:

[0006] X represents cycloalkyl, aryl or heterocyclyl;

[0007] R1, R2, R3, R4 and R5 independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, cycloalkyl, aryl, heterocyclyl, -OR 21 , -SR 21 , -SOR 21 , -(SO2)R 21 , -N(R 21 )2, -O(CO)R 21 , -O(CO)OR 21 , -(CO)R 21 , -(CO)OR 21 or -(CO)N(R 21 )2; the alkyl, alkenyl or alkynyl is optionally substituted with halogen, cyano, nitro, cycloalkyl, aryl, heterocyclyl, -OR 21 , -SR 21 , -SOR 21 , -(SO2)R 21 , -N(R 21 )2, -O(CO)R 21 , -O(CO)OR 21 , -(CO)R 21or - (CO) N (R 21 )2, wherein at least one of the groups is substituted;

[0008] R 21 are each independently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, aryl, heterocyclyl, arylalkyl, or heterocyclylalkyl;

[0009] 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, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R, or -(SO2)R, or two adjacent carbon atoms on the ring form a fused ring with -CH2CH2CH2-, -CH2CH2CH2CH2-, -OCH2CH2-, or -OCH2O- which is unsubstituted or substituted with halogen;

[0010] R is each independently hydrogen, alkyl, alkenyl, alkynyl, alkyl, alkenyl, or alkynyl substituted with at least one group selected from halogen, hydroxy, alkoxy, cyano, or alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl, or phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy.

[0011] In one embodiment, X represents C3-C8 cycloalkyl, aryl, or heterocyclyl;

[0012] R1, R2, R3, R4, R5are each independently hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclyl, -OR 21 , -SR 21 , -SOR 21 , -(SO2)R 21 , -N(R 21 )2, -O(CO)R 21 , -O(CO)OR 21 , -(CO)R 21 , -(CO)OR 21 , or -(CO)N(R 21 )2; said C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl is optionally substituted with at least one group selected from halogen, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclyl, -OR 21 , -SR 21 , -SOR 21, -(SO2)R 21 , -N(R 21 )2, -O(CO)R 21 , -O(CO)OR 21 , -(CO)R 21 or -(CO)N(R 21 )2;

[0013] R 21 are each independently hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, aryl, heterocyclyl, arylC1-C8alkyl or heterocyclylC1-C8alkyl;

[0014] The aforementioned "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, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R, or two adjacent carbon atoms in the ring form a fused ring with -CH2CH2CH2-, -CH2CH2CH2CH2-, -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with halogen;

[0015] R are each independently hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl substituted with at least one group selected from halogen, hydroxy, C1-C8alkoxy, cyano or C1-C8alkoxycarbonyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, C3-C8cycloalkenyl, C3-C8cycloalkenylC1-C8alkyl, phenyl or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C8alkyl, haloC1-C8alkyl, C1-C8alkoxycarbonyl, C1-C8alkylthio, C1-C8alkylsulfonyl, C1-C8alkoxy or haloC1-C8alkoxy.

[0016] In another particular embodiment, X represents C3-C6cycloalkyl, aryl or heterocyclyl;

[0017] R1, R2, R3, R4, R5are independently hydrogen, halogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, cyano, nitro, C3-C6cycloalkyl, aryl, heterocyclyl, -OR 21 , -SR 21 , -SOR 21 , -(SO2)R 21 , -N(R 21 )2, -O(CO)R 21 , -O(CO)OR 21 , -(CO)R 21 , -(CO)OR 21 or -(CO)N(R 21 )2; said C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl is optionally substituted with at least one radical selected from halogen, cyano, nitro, C3-C6cycloalkyl, aryl, heterocyclyl, -OR 21 , -SR 21 , -SOR 21 , -(SO2)R 21 , -N(R 21 )2, -O(CO)R 21 , -O(CO)OR 21 , -(CO)R 21 or -(CO)N(R 21 )2;

[0018] R 21 is independently hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, halogenated C1-C6alkyl, halogenated C2-C6alkenyl, halogenated C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkyl C1-C6alkyl, aryl, heterocyclyl, aryl C1-C6alkyl or heterocyclyl C1-C6alkyl, or two adjacent carbon atoms of the ring form a fused ring with -CH2CH2CH2-, -CH2CH2CH2CH2-, -OCH2CH2- or -OCH2O- unsubstituted or substituted with halogen;

[0019] 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, halogenated C1-C6alkyl, halogenated C2-C6alkenyl, halogenated C2-C6alkynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R;

[0020] R independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl substituted with at least one group selected from halogen, hydroxyl, C1-C6 alkoxy, cyano or C1-C6 alkoxycarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, phenyl or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo-C1-C6 alkoxy.

[0021] In the definitions of compounds shown in the above general formulas and in all the following structural formulas, the technical terms used, whether alone or in compound terms, represent the following substituents: alkyl groups having more than two carbon atoms can be straight-chain or branched. For example, in the compound term "cycloalkylalkyl," the alkyl group can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. The alkyl group is, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such as n-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl, tert-butyl, or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, alkenyl groups are, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl. Alkynyl groups are, for example, ethynyl, propynyl, but-2-yn-1-yl, but-3-yn-1-yl, and 1-methylbut-3-yn-1-yl. Multiple bonds can be in any position in each unsaturated group. Cycloalkyl groups are carbocyclic saturated ring systems having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, cycloalkenyl groups are monocyclic alkenyl groups having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, wherein double bonds can be in any position. Halogens are fluorine, chlorine, bromine, or iodine.

[0022] Unless otherwise specified, the term "aryl" in this invention includes, but is not limited to, phenyl, naphthyl, and... The "heterocyclic group" includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups. and the like, including but not limited to heteroaryl, i.e., aromatic cyclic 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

[0023] 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 will exclude those compounds which are chemically unstable under standard conditions, as known to those skilled in the art.

[0024] 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 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 substituted, the substituents can likewise be substituted at any position, as long as the rules of valence are followed. For example, a heteroaryl group substituted with 1 methyl group may represent and the like. If various functional groups are present, the application also includes any keto and enol tautomeric forms and mixtures and salts thereof.

[0025] The preparation method of the fused heterocyclic compound comprises the following steps:

[0026] The compound shown in general formula II and the compound shown in general formula III are reacted to prepare the compound shown in general formula I, and the reaction equation is as follows:

[0027] wherein, either Q1 or Q2 is halogen, and the other is R1, R2, R3, R4, R5, and X are defined as described above;

[0028] In one specific embodiment, the reaction is carried out in the presence of a solvent.

[0029] In another specific embodiment, the solvent is an organic solvent / water.

[0030] In another embodiment, the organic solvent is selected from at least one of aromatic hydrocarbons (such as toluene, xylene), DMF, DMA, THF, acetonitrile, methanol, ethanol, isopropanol, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate.

[0031] In another embodiment, the base and catalyst are added during the reaction.

[0032] In another embodiment, the base is selected from at least one of inorganic bases (such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KF, CsF, KI, NaI, KOAc, AcONa, K3PO4, t-BuONa, EtONa, NaOH, KOH, NaOMe, NaH, KH, etc.) or organic bases (such as DMAP, pyrazole, triethylamine, DIEA, etc.).

[0033] In another embodiment, the catalyst is selected from at least one of Pd(dppf)Cl2, Pd(dppf)Cl2.CH2Cl2, Pd(OAc)2, PdCl2, Pd(PPh3)4or PdCl2(PPh3)2.

[0034] The present application also provides an intermediate, as shown in general formula II.

[0035] According to the present application, salts of the compounds of the present application, such as salts with bases or acid addition salts, are in each case conventional non-toxic salts, preferably the salts which are agriculturally and / or physiologically acceptable. Preference is given to salts with inorganic bases, such as alkali metal salts (for example sodium, potassium or cesium salts), alkaline earth metal salts (for example calcium or magnesium salts), ammonium salts; or salts with organic bases, in particular with organic amines, such as triethylammonium, dicyclohexylammonium, N,N'-dibenzylethylenediammonium, pyridinium, picolinium or ethanolammonium salts; salts with inorganic acids (for example hydrochlorides, hydrobromides, dihydrogen sulfates, trihydrogen phosphates or phosphates); salts with organic carboxylic or sulfonic acids (for example formates, acetates, trifluoroacetates, maleates, tartrates, methanesulfonates, benzenesulfonates or 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.

[0036] 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.

[0037] The present application also relates to methods 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 methods are, preferably, methods for the surgical treatment and therapeutic treatment of the human or animal body and diagnostic methods which are carried out on the human or animal body.

[0038] The present application also relates to the use of the compounds of the formula I as pesticides, in particular as crop protection agents.

[0039] In the context of the present application, the term "pesticide" also generally includes the term "crop protection agent".

[0040] The compounds of the formula I, which have good plant tolerance, advantageous 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 animal husbandry, in forestry, in gardens and leisure facilities, in plant protection, in the protection of stored products and materials and in the hygiene sector. These compounds are preferably used as pesticides. They are 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.

[0041] At certain concentrations and application rates, the compounds of the 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.

[0042] The present application also relates to formulations comprising at least one compound of the formula I and to the use forms prepared therefrom as insecticides, for example drenches, drip and spray liquids. In certain cases, the use forms comprise other insecticides and / or adjuvants with improving action, such as penetrants, for example vegetable oils (e.g. rapeseed oil, sunflower oil), mineral oils (e.g. paraffin oil), alkyl esters of vegetable fatty acids (e.g. rapeseed oil methyl ester or soybean oil methyl ester), or alkanol alkoxylates; and / or spreaders, for example alkylsilicones and / or salts (e.g. organic or inorganic ammonium or phosphonium salts, for example ammonium sulphate or dihydrogen ammonium phosphate); and / or retention promoters, for example dioctyl sulphosuccinic acid or hydroxypropyl guar polymers; and / or wetters, for example glycerol; and / or fertilizers, for example ammonium-, potassium- or phosphorus-containing fertilizers.

[0043] 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.

[0044] These are preferably formulations or use forms which comprise auxiliaries, such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreezes, biocides, thickeners; and or further auxiliaries, such as adjuvants. In the present context, adjuvants are components which enhance the biological efficacy of the formulation, while 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.

[0045] The formulations are produced in known manner, for example by mixing the compounds of the formula I with auxiliaries, such as extenders, solvents and / or solid carriers and / or further auxiliaries such as surfactants. The formulations are produced either in suitable apparatuses or at the point of use or during application.

[0046] The auxiliaries 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 insecticides, such as spray liquors or seed dressing products, for example particular physical, technical and / or biological properties.

[0047] Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, such as those selected from the group consisting of aromatic or nonaromatic hydrocarbons, such as paraffins, alkylbenzenes, alkyl- naphthalenes, chlorobenzenes, alcohols and polyols, which can optionally also be substituted, etherified and / or esterified, ketones, such as acetone, cyclohexanone, esters, including fatty and oil, and (poly)ethers, unsubstituted and substituted amines, amides, lactams, such as N-alkylpyrrolidones, and lactones, sulfones and sulfoxides, such as dimethyl sulfoxide.

[0048] 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 alkyl- naphthalenes; chlorinated aromatic and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or dichloromethane; aliphatic hydrocarbons, such as cyclohexane or paraffins, such as mineral oil fractions, mineral oils 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.

[0049] In principle, all suitable solvents can be used. Examples of suitable solvents are aromatic hydrocarbons, such as xylene, toluene or alkyl-naphthalenes; chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes, dichloromethane; aliphatic hydrocarbons, such as cyclohexane, paraffins, mineral oil fractions, mineral oils 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.

[0050] 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 likewise 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.

[0051] Liquefied gaseous extenders or solvents can also be used. Particularly suitable extenders or carriers are those which are gaseous at ambient temperatures and atmospheric pressure, for example aerosol propellant gases such as halogenated hydrocarbons, and also butane, propane, nitrogen and carbon dioxide.

[0052] Examples of emulsifiers and / or foaming, dispersing or wetting agents, or mixtures of these surface-active agents, which have ionic or non-ionic properties, are salts of polyacrylic acids; salts of lignosulphonic acid; salts of phenolsulphonic acid or naphthalenesulphonic acid; 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; phosphate esters of polyethoxylated alcohols or phenols; fatty acid esters of polyols; and derivatives of compounds containing sulphates, sulphonates and phosphates, such as alkylaryl 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 the application is carried out in water, the presence of a surface-active agent is advantageous.

[0053] Other auxiliaries which can be present in the formulations and in the use forms derived from them include colorants 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.

[0054] The additional components can be stabilizers which improve the chemical and / or physical stability, such as cold-flow stabilizers, preservatives, antioxidants, light stabilizers or other agents. Foaming and antifoaming agents can also be present.

[0055] Furthermore, the formulations and the use forms derived from them can also comprise as additional adjuvants substances such as sticking agents, such as carboxymethylcellulose, and also natural and synthetic polymers in the form of powders, granules, latices, such as gum arabic, polyvinyl alcohol and polyacrylic acid, or natural and synthetic phospholipids, such as cephalins, lecithins and phosphatidyl cholines. Other possible adjuvants are mineral and vegetable oils.

[0056] Optionally, other adjuvants can be present in the formulations and the use forms derived from them. Examples of such additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic agents, penetration agents, retention promoters, stabilizers, sequestering and chelating agents, humectants and spreading agents. In general, the compounds of the formula I can be combined with any solid or liquid additive which is customary for formulation purposes.

[0057] Useful retention promoters include all those substances which reduce the dynamic surface tension, such as dioctyl sulfosuccinate, or all those substances which increase the viscoelasticity, such as hydroxypropyl guar polymer.

[0058] In the context of the present application, useful penetration agents include all those substances which are customary for enhancing the penetration of active agricultural chemical ingredients into plants. In this context, penetration agents are defined by their ability to penetrate from the (usually aqueous) application liquid and / or from the spray coating into the cuticle of the plants, thereby increasing the mobility of the active ingredients 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 diammonium hydrogenphosphate.

[0059] The formulations preferably comprise from 0.00000001 to 98% by weight of the compound of the formula I, more preferably from 0.01 to 95% by weight of the compound of the formula I, most preferably from 0.5 to 90% by weight of the compound of the formula I, based on the weight of the formulation.

[0060] The content of the compound of the formula I in the use forms prepared from the formulations, especially the insecticides, can vary within wide ranges. The concentration of the compound of the formula I in the use forms can generally be from 0.00000001 to 95% by weight of the compound of the 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.

[0061] The compounds of the formula I can also be used as mixtures with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbicides, beneficial organisms, pesticides, fertilizers, bird repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators, for example to broaden the spectrum of action, to prolong the duration of action, to increase the rate of action, to prevent rejection 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, to drought or to high water content or soil salinity. It is also possible to improve flowering and fruit set 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 harvested products, to prolong the storage period and / or to improve the processing properties of harvested products.

[0062] 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 plant performance such as growth, yield and quality of harvested material.

[0063] 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.

[0064] 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.

[0065] Insecticides / acaricides / nematicides

[0066] The active ingredients mentioned herein under 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

[0067] ​(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.

[0068] (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.

[0069] (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.

[0070] (4) Nicotinic acetylcholine receptor (nAChR) agonists, such as neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor.

[0071] (5) Allosteric activators of nicotinic acetylcholine receptors (nAChR), such as spinosides, such as spintoram and spinosad.

[0072] (6) Chloride channel activators, such as abamectins / milbemycins, such as abamectin, emamectin benzoate, lepimectin and milbemectin.

[0073] (7) Juvenile hormone mimics, such as hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

[0074] (8) Active ingredients with unknown or non-specific mechanisms of action, such as

[0075] Alkyl halides, such as methyl bromide and other alkyl halides; or chloropicrine or thiocyanate or borax or tartar emetic.

[0076] (9) selective feeding blockers, such as pymetrozine or fionicamid.

[0077] (10) mite growth inhibitors, such as clofentezine, hexythiazox and diflovidazin or etoxazole.

[0078] (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, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1.

[0079] (12) oxidative phosphorylation inhibitors, ATP disruptors, such as diafenthiuron or organotin compounds, such as azocyclotin, cyhexatin and fenbutatin oxide or propargite or tetradifon.

[0080] (13) oxidative phosphorylation decouplers interrupting the H+ gradient, such as chlorfenapyr, DNOC and sulfluramid.

[0081] (14) nicotinic acetylcholine receptor agonists, such as bensultap, cartap hydrochloride, thiocyclam and thiosultap-sodium.

[0082] (15) Inhibitors of chitin biosynthesis, type 0, for example bistrifluron, chlofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

[0083] (16) Inhibitors of chitin biosynthesis, type 1, for example buprofezin.

[0084] (17) Moulting disruptor (especially for Diptera, i.e. flies), for example cyromazine.

[0085] (18) Ecdysone receptor agonists, for example chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0086] (19) Octopaminergic agonists, for example amitraz.

[0087] (20) Complex-III electron transport inhibitors, for example hydramethylnone, or acequinocyl, or fluacrypyrim.

[0088] (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.).

[0089] (22) Voltage-gated sodium channel blockers, for example indoxacarb or metaflumizone.

[0090] (23) Inhibitors of acetyl-CoA carboxylase, for example tetronic and tetramic acid derivatives, such as spirodiclofen, spiromesifen and spirotetramat.

[0091] (24) Complex-IV electron transport inhibitors, for example phosphines, such as aluminium phosphide, calcium phosphide, phosphine and zinc phosphide; or cyanides.

[0092] (25) Complex-II electron transport inhibitors, for example cyenopyrafen and cyflumetofen.

[0093] (28) Ryanodine receptor effectors, for example diamides, such as chlorantraniliprole, cyantraniliprole and flubendiamide;

[0094] 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] pthalic acid amide (known from WO 2012 / 034472), 8-Chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyrimidine-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-pentylenehydrazinecarbodithioic acid amide (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),

[0095] fungicides

[0096] 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).

[0097] (1) Inhibitors of the biosynthesis of ergosterol, for example (1.1) aldimorph, (1.2) azaconazole, (1.3) bitertanol, (1.4) bromuconazole, (1.5) cyproconazole, (1.6) diclobutrazol, (1.7) difenoconazole, (1.8) diniconazole, (1.9) diniconazole-M, (1.10) dodemorph, (1.11) dodemorph acetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16) fenhexamid, (1.17) fenpropidin, (1.18) fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22) flutriafole, (1.23) furconazole, (1.24) furconazole-cis, (1.25) hexaconazole, (1.26) imazalil, (1.27) imazalil sulfate, (1.28) imibenconazole, (1.29) ipconazole, (1.30) metconazole, (1.31) myclobutanil, (1.32) naftifine, (1.33) nuarimol, (1.34) oxpoconazole, (1.35) paclobutrazol, (1.36) pfurazoate, (1.37) penconazole, (1.38) piperalin, (1.39) prochloraz, (1.40) propiconazole, (1.41) (propiconazole-M), (1.42) rafoxanide, (1.43) spiroxamine, (1.44) tricarbamide, (1.45) triforine, (1.46) uniconazole, (1.47) uniconazole-P, (1.48) XRD-1762, (1.49) xylogilvan, (1.50) 3-(4-chloro-2- thiazolyl)-4-(4-chlorophenyl)-1,2,5-thiadiazole, (1.51) 2-(2,4-dichlorophenyl)-1,3- dimethyl-1,3-dihydro-2H-imidazol-4-one, (1.52) 2-(2,4-dichlorophenyl)-1,3-dimethyl- 1,3-dihydro-2H-imidazol-4-one, (1.53) 2-(4-chlorophenyl)-1,3-dimethyl-1,3-dihydro-2H- imidazol-4-one, (1.54) 2-(4-chlorophenyl)-1,3-dimethyl-1,3-dihydro-2H-imidazol-4-one, (1.55) 2-(4-chlorophenyl)-1,3-dimethyl-1,3-dihydro-2H-imidazol-4-one, (1.56) 2-41) prothioconazole, (1.42) pyributicarb, (1.43) pyrifenox, (1.44) quinconazole, (1.45) simeconazole, (1.46) spiroxamine, (1.47) tebuconazole, (1.48) terbinafine, (1.49) tetraconazole, (1.50) triadimefon, (1.51) triadimenol, (1.52) tridemorph, (1.53) triflumizole, (1.54) triforine, (1.55) triticonazole, (1.56) uniconazole, (1.57) uniconazole-P, (1.58) viniconazole, (1.59) voriconazole, (1.60) 1-(4-chlorophenyl)-2-(1 H-1,2,4-triazol-1-yl)cycloheptanol, (1.61) 1-(2,2-dimethyl-2,3-dihydro-1 H-inden-1-yl)-1 H-imidazole-5-carboxylic acid methyl ester, (1.62) N'-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidocarbamamide, (1.63) N-ethyl-N-methyl-N'-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidocarbamamide, (1.64) o-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl] 1 H-imidazole-1 -thioate, (1.65) pyrisoxazole.

[0098] (2) Respiratory inhibitors (respiratory chain inhibitors), for example (2.1) bixafen, (2.2) boscalid, (2.3) carboxin, (2.4) diflumetorim, (2.5) fenfuram, (2.6) fluopyram, (2.7) flutolanil, (2.8) fluxapyroxad, (2.9) furametpyr, (2.10) furmecyclox, (2.11) mixtures of pyraclostrobin of the cis and trans epimeric racemates 1 RS, 4SR, 9RS and 1 RS, 4SR, 9SR, (2.12) pyraclostrobin (trans epimeric racemate), (2.13) pyraclostrobin (trans epimeric racemate 1 R, 4S, 9S), (2.14) pyraclostrobin (trans epimeric racemate 1 S, 4R, 9R), (2.15) pyraclostrobin (cis epimeric racemate 1 RS, 4SR, 9RS), (2.16) pyraclostrobin (cis epimeric racemate 1 R, 4S, 9R), (2.17) pyraclostrobin (cis epimeric racemate 1 S, 4R, 9S), (2.18) mepronil, (2.19) oxycarboxin, (2.20) penflufen, (2.21) penthiopyrad, (2.22) sedaxane, (2.23) thifluzamide, (2.24) 1 -methyl- N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1 H-pyrazole-4- carboxamide, (2.25) 3-(difluoromethyl)-1 -methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]- 1 H-pyrazole-4-carboxamide, (2.26) 3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3- hexafluoropropoxy)phenyl]-1 -methyl-1 H-pyrazole-4-carboxamide, (2.27) N-[1 -(2,4- dichlorophenyl)-1 -methoxypropan-2-yl]-3-(difluoromethyl)-1 -methyl-1 H-pyrazole-4- carboxamide, (2.28) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2- yl]oxy}phenyl)ethyl]quinazoline-4-amine, (2.29) benzovindiflupyr, (2.30) diclocymet30) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-l,4-methanonaphthalen-5-yl]-3- (difluoromethyl)-l-methyl-lH-pyrazole-4-carboxamide, and (2.31) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-l,4-methanonaphthalen-5-yl]-3- (difluoromethyl)-l-methyl-lH-pyrazole-4-carboxamide, (2.32) 3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxylic acid N-(l,l,3-trimethyl-2,3- dihydro-lH-inden-4-yl)amide, (2.33) l,3,5-trimethyl-lH-pyrazole-4-carboxylic acid N-(l,l,3-trimethyl-2,3-dihydro-lH- inden-4-yl)amide, (2.34) l-methyl-3-(trifluoromethyl)-lH-pyrazole-4-carboxylic acid N-(l,l,3-trimethyl- 2,3-dihydro-lH-inden-4-yl)amide, (2.35) l-methyl-3-(trifluoromethyl)-lH-pyrazole-4- carboxylic acid N-[(lR)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]amide, (2.36) l-methyl-3-(trifluoromethyl)-lH-pyrazole-4-carboxylic acid N-[(lS)-l,l,3- trimethyl-2,3-dihydro-lH-inden-4-yl]amide, (2.37) 3-(difluoromethyl)-l-methyl-lH-pyrazole- 4-carboxylic acid N-[(3S)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]amide, (2.38) 3- (difluoromethyl)-l-methyl-lH-pyrazole-4-carboxylic acid N-[(3R)-l,l,3-trimethyl-2,3- dihydro-lH-inden-4-yl]amide, (2.39) l,3,5-trimethyl-lH-pyrazole-4-carboxylic acid N-[(3R)- 1,1,3-trimethyl-2,3-dihydro-lH-inden-4-yl]amide, (2.40) l,3,5-trimethyl-lH-pyrazole-4- carboxylic acid N-[(3S)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]amide, (2.41) benodanil, (2.42) 2-chloro-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)pyridine-3-carboxamide, (2.43) isofetamid.

[0099] (3) Respiratory inhibitors acting on complex-III of the respiratory chain (respiration inhibitors), for example (3.1) ametoctradin, (3.2) amisulbrom, (3.3) azoxystrobin, (3.4) cyazofamid, (3.5) coumethoxystrobin, (3.6) coumoxystrobin, (3.7) dimoxystrobin, (3.8) enestroburin, (3.9) famoxadone, (3.10) fenamidone, (3.11) flufenoxystrobin, (3.12) fluoxastrobin, (3.13) kresoxim-methyl, (3.14) metominostrobin, (3.15) orysastrobin, (3.16) picoxystrobin, (3.17) pyraclostrobin, (3.18) pyrametostrobin, (3.19) pyraoxystrobin, (3.20) pyribencarb, (3.21) triclopyricarb, (3.22) trifloxystrobin, (3.23) (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide, (3.24) (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1 E)-1 -[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)acetamide, (3.25) (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1 -[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}acetamide, (3.26) (2E)-2-{2-[({[(1 E)-1 -(3-{[(E)-1 -fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.27) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.28) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.29) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.30) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.31) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.32) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.33) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.34) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.35) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.36) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.37) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.38) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.39) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.40) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.41) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.42) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.43) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.44) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.45) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.46) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.47) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.48) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.49) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N28) 2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)pyridine-3- carboxamide, (3.29) 5-methoxy-2-methyl 4-(2-{[({(1 E)-1 -[3-(trifluoromethyl)phenyl]ethylidene} amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, (3.30) methyl (2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}thio)methyl]phenyl}-3- methoxypropyl-2-enoate, (3.31) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3- (carbamoyl)-2-hydroxybenzamide, (3.32) 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2- methoxy-N-methylacetamide.

[0100] (4) Mitosis and cell division inhibitors such as (4.1) benomyl, (4.2) carbendazim, (4.3) chlorfenazole, (4.4) diethofencarb, (4.5) ethaboxam, (4.6) fluopicolid, (4.7) fuberidazole, (4.8) pencycuron, (4.9) thiabendazole, (4.10) thiophanate-methyl, (4.11) thiophanate, (4.12) zoxamide, (4.13) 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine, (4.14) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine.

[0101] (5) Compounds with multisite activity, for example (5.1) Bordeaux mixture, (5.2) captafol, (5.3) captan, (5.4) chlorothalonil, (5.5) copper hydroxide, (5.6) copper naphthenate, (5.7) copper oxide, (5.8) copper oxychloride, (5.9) copper sulfate, (5.10) dichlofluanid, (5.11) dithianon, (5.12) dodine, (5.13) dodine free base, (5.14) ferbam, (5.15) fluorofolpet, (5.16) folpet, (5.17) guazatine, (5.18) guazatine acetate, (5.19) iminoctadine, (5.20) iminoctadine albesilate, (5.21) iminoctadine triacetate, (5.22) mancopper, (5.23) mancozeb, (5.24) maneb, (5.25) metiram, (5.26) zinc metiram, (5.27) oxine-copper, (5.28) propamidine, (5.29) propineb, (5.30) sulfur and sulfur preparations such as calcium polysulfide, (5.31) thiram, (5.32) tolylfluanid, (5.33) zineb, (5.34) ziram and (5.35) anilazine.

[0102] (6) Resistance inducers, for example (6.1) acibenzolar-S-methyl, (6.2) isotianil, (6.3) probenazole, (6.4) tiadinil and (6.5) laminarin.

[0103] (7) Inhibitors of the amino acid and protein biosynthesis, for example (7.1) blasticidin-S, (7.2) cyprodinil, (7.3) kasugamycin, (7.4) kasugamycin hydrochloride hydrate, (7.5) mepanipyrim, (7.6) pyrimethanil, (7.7) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-l-yl)quinoline and (7.8) oxytetracycline and (7.9) streptomycin.

[0104] (8) Inhibitors of the ATP production, for example (8.1) fentin acetate, (8.2) fentin chloride, (8.3) fentin hydroxide, (8.4) silthiofam.

[0105] (9) Inhibitors of the cell wall synthesis, for example (9.1) benthiavalicarb, (9.2) dimethomorph, (9.3) flumorph, (9.4) iprovalicarb, (9.5) mandipropamid, (9.6) polyoxins, (9.7) polyoxorim, (9.8) validamycin A, (9.9) valifenalate and (9.10) polyoxin B.

[0106] (10) Lipid and membrane synthesis inhibitors, for example (10.1) biphenyl, (10.2) chloroneb, (10.3) dicloran, (10.4) edifenphos, (10.5) etridiazole, (10.6) iodocarb, (10.7) iprobenfos, (10.8) isoprothiolane, (10.9) propamocarb, (10.10) propamocarb hydrochloride, (10.11) prothiocarb, (10.12) pyrazophos, (10.13) quintozene, (10.14) tecnazene and (10.15) tolclofos-methyl.

[0107] (11) Melanin biosynthesis inhibitors, for example (11.1) carpropamid, (11.2) diclocymet, (11.3) fenoxanil, (11.4) fthalide, (11.5) pyroquilon, (11.6) tricyclazole, (11.7) 2,2,2-trifluoroethyl {3-methyl-l-[(4-methylbenzoyl)amino]butan-2-yl} carbamate;

[0108] (12) Nucleic acid synthesis inhibitors, for example (12.1) benalaxyl, (12.2) benalaxyl-M (kiralaxyl), (12.3) bupirimate, (12.4) clozylacon, (12.5) dimethirimol, (12.6) ethirimol, (12.7) furalaxyl, (12.8) hymexazol, (12.9) metalaxyl, (12.10) metalaxyl-M (mefenoxam), (12.11) ofurace, (12.12) oxadixyl, (12.13) oxolinic acid and (12.14) octhilinone.

[0109] (13) signal transduction inhibitors, for example (13.1) chlozolinate, (13.2) fenpiclonil, (13.3) fludioxonil, (13.4) iprodione, (13.5) procymidone, (13.6) quinoxyfen, (13.7) vinclozolin and (13.8) proquinazid;

[0110] (14) decouplers, for example (14.1) binapacryl, (14.2) dinocap, (14.3) ferimzone, (14.4) fluazinam and (14.5) meptyldinocap.

[0111] (15) other compounds, for example (15.1) benthiazole, (15.2) bethoxazine, (15.3) capsimycin, (15.4) carvone, (15.5) chinomethionat, (15.6) pyriofenone (chlazafenone), (15.7) cufraneb, (15.8) cyflufenamid, (15.9) cymoxanil, (15.10) cyprosulfamide, (15.11) dazomet, (15.12) debacarb, (15.13) dichlorophen, (15.14) diclomezine, (15.15) difenzoquat, (15.16) difenzoquat methylsulphate, (15.17) diphenylamine, (15.18) EcoMate, (15.19) fenpyrazamine, (15.20) flumetover, (15.21) fluorimid, (15.22) flusulfamide, (15.23) flutianil, (15.24) fosetyl-aluminium, (15.25) fosetyl-calcium, (15.26) fosetyl-sodium, (15.27) hexachlorobenzene, (15.28) irumamycin, (15.29) methasulfocarb, (15.30) methylisothiocyanate, (15.31) metrafenone, (15.32) mildiomycin, (15.33) natamycin, (15.34) nickel dimethyldithiocarbamate, (15.35) nitrothal-isopropyl, (15.36) octhilinone, (15.37) oxamocarb, (15.38) oxyfenthiin, (15.39) phenisopham, (15.40) propamocarb, (15.41) propineb, (15.42) phthalide, (15.43) pyroquilon, (15.44) tebufloquin, (15.45) tolnaftate, (15.46) carboxin, (15.47) fenpiclonil, (15.48) flusul- famide, (15.49) spicinomycin, (15.50) acrinathrin, (15.51) amidoflumet, (15.52) clofentezine, (15.53) chlordane, (15.54) endosulfan, (15.55) ethiprole, (15.56) fipronil, (15.57) hexythi- oxycarb, (15.58) imicyafos, (15.59) lufenuron, (15.60) metoxadiazone, (15.61) profenofos, (15.62) pyridaben, (15.63) sulfoxaflor, (15.64) tetranactide, (15.65) triarathene, (15.66) triazamate, (15.67) tri- azophos, (15.68) acetoprole, (15.69) amidoflumet, (15.70) benclothiaz, (15.71) benzox- afluor, (15.72) bistrimol, (15.73) brofluthrinate, (15.74) chlorobenzilate, (15.75) clo- thiaquon, (15.76) cyanofenpham, (15.77) cyanthoate, (15.78) dicofol, (15.79) etofenprox, (15.80) fenbutatin-oxide, (15.81) fenkodion, (15.82) flucycloxuron, (15.83) flufen- oxuron, (15.84) formothion, (15.85) hexythidene, (15.86) metoxadiazone, (15.87) mil- bactam, (15.88) pirimetaphan, (15.89) propargite, (15.90) quinomethionate, (15.91)39) pentachlorophenol and its salts, (15.40) phenothrin, (15.41) phosphoric acid and its salts, (15.42) propamocarb-fosetylate, (15.43) propanosine-sodium, (15.44) pyrimorph, (15.45) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4- yl)prop-2-en-1-one, (15.46) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1- (morpholin-4-yl)prop-2-en-1-one, (15.47) pyrrolnitrin, (15.48) tebufloquin, (15.49) tecloftalam, (15.50) tolnifanide, (15.51) triazoxide, (15.52) trichlamide, (15.53) zarilamid, (15.54) (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4- methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2- methylpropanoate, (15.55) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2- oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H- pyrazol-1-yl]ethanone, (15.56) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2- oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H- pyrazol-1-yl]ethanone, (15.57) 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2- oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H- pyrazol-1-yl]ethanone, (15.58) 1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl 1H- imidazole-1-carboxylate, (15.59) 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine, (15.60) 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, (15.61) 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone, (15.62) 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone, (15.63) 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone, (15.64) 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone, (15.65) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.66) 2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine, (15.67) 2-phenylphenol and salts thereof, (15.68) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.69) 3,4,5-trichloropyridine-2,6-dicarbonitrile, (15.70) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (15.71) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (15.72) 5-amino-1,3,4-thiadiazole-2-thiol, (15.73) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide, (15.74) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.75) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.76) 5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, (15.77) (2z)-3-amino-2-cyano-3-phenylacrylate, (15.78) N'-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidocarbamide, (15.79) N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide, (15.80) N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide, (15.81) N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide, (15.82) N-[l-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide, (15.83) N-[l-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide, (15.84) N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2- phenylacetamide, (15.85) N-{(z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2- phenylacetamide, (15.86) N'-{4-[(3-tert-butyl-4-cyano-l,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N- ethyl-N-methylimidocarbamide, (15.87) N-methyl-2-(l-{[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-N-(l,2,3,4- tetrahydronaphthalen-l-yl)-l,3-thiazole-4-carboxamide, (15.88) N-methyl-2-(l-{[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-N- [(lR)-l,2,3,4-tetrahydronaphthalen-l-yl]-l,3-thiazole-4-carboxamide, (15.89) N-methyl-2-(l-{[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-N- [(lS)-l,2,3,4-tetrahydronaphthalen-l-yl]-l,3-thiazole-4-carboxamide, (15.90) phenyl {6-[({[(l-methyl-lH-tetrazol-5-yl)(phenyl)methyl]amino}oxy)methyl]pyridin-2- yl}carbamate, (15.91) phenazin-1-carboxylic acid, (15.92) quinolin-8-ol, (15.93) quinolin-8-ol sulfate (2: 1), (15.94) tert-butyl {6-[({[(l-methyl-lH-tetrazol-5-yl)(phenyl)methyl]amino}oxy)methyl]pyridin-2- yl}carbamate, (15.95) l-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)diphenyl-2-yl]-lH-pyrazole-4- carboxamide, (15.96) N-(4'-chlorodiphenyl-2-yl)-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxamide, (15.97) N-(2',4'-dichlorodiphenyl-2-yl)-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxamide, (15.98) 3-(difluoromethyl)-l-methyl-N-[4'-(trifluoromethyl)diphenyl-2-yl]-lH-pyrazole-4- carboxamide, (15.99) N-(2',5'-difluorobiphenyl-2-yl)-l-methyl-3-(trifluoromethyl)-lH-pyrazole-4- carboxamide, (15.100) 3-(difluoromethyl)-l-methyl-N-[4'-(prop-l-yn-l-yl)biphenyl-2-yl]-lH- pyrazole-4-carboxamide, (15.101) 5-fluoro-l,3-dimethyl-N-[4'-(prop-l-yn-l-yl)biphenyl-2- yl]-lH-pyrazole-4-carboxamide, (15.102) 2-chloro-N-[4'-(prop-l-yn-l-yl)biphenyl-2- yl]nicotinamide, (15.103) 3-(difluoromethyl)-N-[4'-(3,3-dimethylbut-l-yn-l-yl)biphenyl-2- yl]-l-methyl-lH-pyrazole-4-carboxamide, (15.104) N-[4'-(3,3-dimethylbut-l-yn-l-yl)biphenyl- 2-yl]-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide, (15.105) 3-(difluoromethyl)-N-(4'- ethynylbiphenyl-2-yl)-l-methyl-lH-pyrazole-4-carboxamide, (15.106) N-(4'-ethynylbiphenyl- 2-yl)-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide, (15.107) 2-chloro-N-(4'- ethynylbiphenyl-2-yl)nicotinamide, (15.108) 2-chloro-N-[4'-(3,3-dimethylbut-l-yn-l-yl)biphenyl- 2-yl]nicotinamide, (15.109) 4-(difluoromethyl)-2-methyl-N-[4'-(trifluoromethyl)biphenyl-2-yl]- 1,3-thiazole-5-carboxamide, (15.110) 5-fluoro-N-[4'-(3-hydroxy-3-methylbut-l-yn-l-yl)biphenyl- 2-yl]-l,3-dimethyl-lH-pyrazole-4-carboxamide, (15.111) 2-chloro-N-[4'-(3-hydroxy-3- methylbut-l-yn-l-yl)biphenyl-2-yl]nicotinamide, (15.112) 3-(difluoromethyl)-N-[4'-(3- methoxy-3-methylbut-l-yn-l-yl)biphenyl-2-yl]-l-methyl-lH-pyrazole-4-carboxamide, (15.113) 5-fluoro-N-[4'-(3-methoxy-3-methylbut-l-yn-l-yl)biphenyl-2-yl]-l,3-dimethyl-lH- pyrazole-4-carboxamide, (15.114) 2-chloro-N-[4'-(3-methoxy-3-methylbut-l-yn-l-yl)biphenyl- 2-yl]nicotinamide, (15.115) (5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4- trimethoxy-6-methylphenyl)methanone, (15.116) N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulfonyl)valinamide, (15.117) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.118) but-3-yn-1-yl {6-[({[(z)-(1-methyl-1 H-tetrazol-5-yl)(phenyl)methyl]amino}oxy)methyl]pyridin-2- yl}carbamate, (15.119) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(1 H)-one), (15.120) 3,4,5-trihydroxybenzoic acid propyl ester, (15.121) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)-1 H-pyrazole-4-carboxamide, (15.122) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl]-1 H-pyrazole-4-carboxamide, (15.123) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl]-1 H-pyrazole-4-carboxamide, (15.124) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.125) (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.126) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.127) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thione, (15.128) 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl-2-yl]methyl}-1 H-1,2,4-triazol-5-yl isothiocyanate, (15.129) 5-(allylthio)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl-2-yl]methyl}-1 H-1,2,4-triazole, (15.130) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, (15.131) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thione, (15.132) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}- 2,4-dihydro-3H-1,2,4-triazol-3-thione, (15.133) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2- (2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (15.134) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}- 1H-1,2,4-triazol-5-yl thiocyanate, (15.135) 5-(allylthio)-1-{[rel(2R,3S)-3-(2- chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (15.136) 5-(allylthio)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2- yl]methyl}-1H-1,2,4-triazole, (15.137) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5- hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, (15.138) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]- 2,4-dihydro-3H-1,2,4-triazol-3-thione, (15.139) 2-[(2R,4R,5R)-1-(2,4- dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4- triazol-3-thione, (15.140) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, (15.141) 2-[(2S,4S,5R)- 1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4- triazol-3-thione, (15.142) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, (15.143) 2-[(2R,4R,5S)- 1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4- triazol-3-thione, (15.144) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]- 2,4-dihydro-3H-1,2,4-triazol-3-thione, (15.145) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3- trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (15.146) 2-(6-benzylpyridin-2-yl)quinazoline, (15.147) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15.148) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.149) abscisic acid, (15.150) 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6- trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide, (15.151) N'-[5-bromo-6-(2,3- dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidocarbamide, (15.152) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N- methylimidocarbamide, (15.153) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2- methylpyridin-3-yl}-N-ethyl-N-methylimidocarbamide, (15.154) N'-{5-bromo-6-[(1S)-1- (3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidocarbamide, (15.155) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N- ethyl-N-methylimidocarbamide, (15.156) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]- 2-methylpyridin-3-yl}-N-ethyl-N-methylimidocarbamide, (15.157) N-cyclopropyl-3- (difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (15.158) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1- methyl-1H-pyrazole-4-carboxamide, (15.159) N-(2-tert-butylbenzyl)-N-cyclopropyl-3- (difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.160) N-(5-chloro-2- ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4- carboxamide, (15.161) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1- methyl-1 H-pyrazole-4-carboxamide, (15.162) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1- methyl-1 H-pyrazole-4-carboxamide, (15.163) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1- methyl-1 H-pyrazole-4-carboxamide, (15.164) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1- methyl-1 H-pyrazole-4-carboxamide, (15.165) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1- methyl-1 H-pyrazole-4-carboxamide, (15.166) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1- methyl-1 H-pyrazole-4-carboxamide, (15.167) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1- methyl-1 H-pyrazole-4-carboxamide, (15.168) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1- methyl-1 H-pyrazole-4-carboxamide, (15.169) N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1- methyl-1 H-pyrazole-4-carboxamide, (15.170) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1- methyl-1 H-pyrazole-4-carboxamide, (15.171) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1- methyl-1 H-pyrazole-4-carboxamide, (15.172) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2- (trifluoromethyl)benzyl]-1 H-pyrazole-4-carboxamide, (15.173) N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1- methyl-1 H-pyrazole-4-carboxamide, (15.174) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3- (difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide, (15.175) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1- methyl-1 H-pyrazole-4-carboxamide, (15.176) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1 H- pyrazole-4-thiocarboxamide, (15.177) 3-(Difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)-1 - methyl-1 H-pyrazole-4-carboxamide, (15.178) 3-(Difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4- yl]-1 -methyl-1 H-pyrazole-4-carboxamide, (15.179) 3-(Difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4- yl]-1 -methyl-1 H-pyrazole-4-carboxamide, (15.180) N'-(2,5-Dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidocarbamide, (15.181 ) N'-{4-[(4,5-Dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N- methylimidocarbamide, (15.182) N-(4-Chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1 H- pyrazol-5-amine. If appropriate, all the mixed components mentioned under (1 ) to (15) can form salts with suitable bases or acids, if this is possible on the basis of their functional groups.

[0112] Biological pesticides as mixed components

[0113] The compounds of the formula I can be combined with biological pesticides.

[0114] Biological pesticides include, inter alia, bacteria, fungi, yeasts, plant extracts and products of microbial origin, including proteins and secondary metabolites.

[0115] Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria which act as bioinsecticides, biofungicides or bionematicides.

[0116] 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.

[0117] Safety agents as mixed components

[0118] 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-[(methylaminocarbonyl)amino]phenyl}sulfanyl)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).

[0119] Plants and plant parts

[0120] All plants and their parts can be treated in accordance with the application. By plants is meant in this context all plants and their parts, e.g. 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 including the plant cultivars which are protected by plant breeders’ rights and which have been developed by means of naturally occurring mutations or hybridization. By plant parts is meant in this context all parts and organs of the plants above and below ground such as shoot, leaf, flower and root, given as examples leaf, needle, stem, trunk, flower, fruit and seed, and also roots and rhizomes. Plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes and seeds.

[0121] The treatment of plants and plant parts with the compounds of the formula I according to the application is carried out directly by the customary treatment methods, for example by immersion, spraying, vaporizing, atomizing, spreading, brushing, injecting, and in the case of propagation material, in particular seeds, also by one or more coats. The treatment according to the application is carried out directly before the plants are planted out or before the seeds are sown.

[0122] As mentioned above, all plants and their parts can be treated in accordance with the application. In a preferred embodiment, wild plant 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, if appropriate in combination with conventional methods (genetically modified organisms), and their parts are treated. The term "parts" is to be understood to mean all parts of plants, such as foliage, seeds, fruits, and vegetative parts.

[0123] Transgenic plants, seed treatment and inteeration events

[0124] 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.

[0125] Crop protection – types of treatment

[0126] 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.

[0127] 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.

[0128] 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.

[0129] Seed treatment

[0130] The control of animal pests by treating plant seeds is known for a long time 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 ingredient 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.

[0131] 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.

[0132] 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.

[0133] 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.

[0134] 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.

[0135] 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 develops 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.

[0136] 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.

[0137] It is likewise considered advantageous that the compounds of formula I can also be used, inter alia, for transgenic seed.

[0138] 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.

[0139] 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.

[0140] 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.

[0141] 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.

[0142] 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.

[0143] 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.

[0144] 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.

[0145] 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.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] 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.

[0151] 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.

[0152] Useful binders which can be present in the seed dressing formulations used according to the application are all binders which can be used in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

[0153] Gibberellins which can be present in the seed dressing formulations used according to the application are preferably gibberellin A1, A3 (= gibberellic acid), A4 and A7, particularly preferred is the use of gibberellic acid.

[0154] The seed dressing formulations used according to the application can be used to treat a large number of different kinds of seed, either directly or after prior dilution with water. For example, the concentrates or the formulations obtained from them 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 formulations used according to the application or their dilution forms for use can also be used to dress the seeds of transgenic plants.

[0155] For the treatment of the seed with the seed dressing formulations used according to the application or the use forms produced from them, all the mixing apparatuses which are customary for seed dressing are available. More specifically, the process for seed dressing is: the seeds are placed in batches or continuously in a mixer; the particular required amount of seed dressing formulation, either as such or after prior dilution with water, is added; and mixing is carried out until the formulation is uniformly distributed over the seeds. If appropriate, a drying operation can be carried out subsequently.

[0156] The application rates for the seed dressing formulations used according to the application can vary within a relatively wide range. They depend on the particular content of compounds of the formula I in the formulation and on the seeds. The application rates for the compounds of the formula I are generally from 0.001 g to 50 g per kg of seeds; preferably from 0.01 g to 15 g per kg of seeds.

[0157] For animal health

[0158] 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 flies (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.

[0159] 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.

[0160] 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.

[0161] 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.

[0162] In a preferred embodiment, the compounds of formula I are administered to mammals.

[0163] In another preferred embodiment, the compounds of formula I are administered to avians, i.e. caged birds and in particular poultry.

[0164] 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, hides, eggs, honey, etc.) so that animal keeping can be more economical and simple and better keeping of the animals in good condition is achieved.

[0165] 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.

[0166] 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.

[0167] 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.

[0168] 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.

[0169] 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.

[0170] Vector control

[0171] 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).

[0172] 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.

[0173] 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.

[0174] If the compounds of the formula I are resistant to destruction, then vector control is also possible.

[0175] The compounds of the formula I are suitable for the protection of animals and / or humans against infestation and / or infection by parasites, in particular ectoparasites and endoparasites.

[0176] Protection of industrial materials

[0177] The compounds of the formula I are suitable for protecting industrial materials against attack or damage by insects, for example insects from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.

[0178] 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 worked wood products and coating compositions. Particular preference is given to the use of the application for the protection of wood.

[0179] 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.

[0180] In a further embodiment, the compounds of the formula I are ready-to-use insecticides, meaning that they can be applied to the materials without further modification. In particular, suitable further insecticides or fungicides are those mentioned above.

[0181] Surprisingly, it has also been found that the compounds of the formula I can be used for protecting objects which come into contact with salt water or slightly brackish water from fouling, in particular 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.

[0182] Control of animal pests in the hygiene sector

[0183] 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.

[0184] 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.

[0185] 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

[0186] 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.

[0187] In view of the economy and diversity of the compounds, we have preferably synthesized some of the compounds, among the synthesized compounds, some are listed in Table 1 below. The specific compound structure and the corresponding compound information are shown in Table 1 and Table 2. 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.

[0188] Table 1 Compound structure

[0189] Table 2 Compounds 1 H NMR

[0190] Several methods for preparing the compounds of the present application are illustrated in the following Schemes and Examples. Starting materials can be obtained from commercial sources or made by known literature methods or as illustrated. 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 Schemes below, other suitable starting materials and conditions can readily be found by those skilled in the art and are included in the present application. In addition, the synthetic methods described below can be further modified to produce alternative synthetic routes. For example, protection and deprotection of appropriate groups can be carried out at various stages in the reaction sequences described below.

[0191] The following method examples are provided to further illustrate the synthetic methods of the present application, the specific materials, amounts and conditions used are not intended to limit the scope of the application. The reagents used in the synthesis of the compounds described below can be obtained from commercial sources or readily prepared by one of ordinary skill in the art.

[0192] Representative compounds are synthesized as follows, and other compounds are synthesized in a similar manner.

[0193] 1. Synthesis of compound 4

[0194] (1) Compound 4-1 (2 g, 12.26 mmol) and compound 4-2 (4.55 g, 12.26 mmol) were dissolved in 20 mL of acetonitrile, and the reaction was carried out at 120 °C under nitrogen overnight. After the reaction was completed, the reaction solution was concentrated and purified by silica gel column chromatography (EA / PE = 40%) to obtain 4-3 (brown solid, 950 mg, 2.18 mmol, yield 17.8%).

[0195] (2) 4-3 (250 mg, 0.57 mmol) was dissolved in 1,4-dioxane, 4-4 (219 mg, 0.86 mmol), potassium acetate (140.9 mg, 1.44 mmol) and Pd(dppf)Cl2(23 mg, 0.03 mmol) were added, and the reaction was carried out at 100°C under nitrogen overnight. After the reaction was completed, the reaction solution was reduced to room temperature, filtered with diatomite, extracted with water and ethyl acetate (30 mL*3), and the solvent was removed to obtain crude 4-5 (brown oil, 250 mg, 0.52 mmol, yield 91.2%).

[0196] (3) Compound 4-5 (200 mg, 0.41 mmol) was dissolved in 10 mL of a mixed solvent of 1,4-dioxane: water = 4:1, 4-6 (112 mg, 0.62 mmol), cesium fluoride (156 mg, 1.03 mmol) and Pd(dppf)Cl2(22 mg, 0.03 mmol) were added, and the reaction was carried out at 85°C under nitrogen overnight. After the reaction was completed, water and ethyl acetate (30 mL*3) were added, and the organic phase was purified by silica gel column chromatography (EA / PE = 27%) to obtain white solid compound 4 (90 mg, yield 43.4%, 0.18 mmol).

[0197] 2. Synthesis of compound 2

[0198] 4-5 (250 mg, 0.52 mmol) was dissolved in 10 mL of a mixed solvent of 1,4-dioxane: water = 4:1, 2-1 (138 mg, 0.78 mmol), cesium fluoride (197 mg, 1.3 mmol) and Pd(dppf)Cl2(22 mg, 0.03 mmol) were added, and the reaction was carried out at 85°C under nitrogen overnight. After the reaction was completed, water and ethyl acetate (30 mL*3) were added, and the organic phase was purified by silica gel column chromatography (EA / PE = 27%) to obtain white solid compound 2 (51 mg, yield 21.7%, 0.11 mmol).

[0199] 3. Synthesis of compound 3

[0200] Compound 4-5 (166 mg, 0.34 mmol) was dissolved in 10 mL of a mixed solvent of 1,4-dioxane:water = 4:1, 3-1 (100 mg, 0.52 mmol), cesium fluoride (131 mg, 0.86 mmol) and Pd(dppf)Cl2(14 mg, 0.02 mmol) were added, and the reaction was carried out at 85°C under nitrogen protection overnight. After the reaction was completed, water and ethyl acetate (30 mL*3) were added for extraction, and the organic phase was purified by silica gel column chromatography (EA / PE = 25%) to obtain white solid compound 3 (50 mg, yield 31.0%, 0.11 mmol).

[0201] 4. Synthesis of compound 127

[0202] Compound 4-5 was dissolved in Dioxane (10.0 mL) and H2O (1.0 mL), and 127-1 (97 mg, 1.10 eq), cesium fluoride (157 mg, 3.00 eq) and Pd(dppf)Cl2(14 mg, 0.05 eq) were added in turn, N2was replaced three times, and the temperature was raised to 100°C for overnight reaction. The reaction solution was diluted with acetonitrile and sent to LCMS for monitoring, and the raw material disappeared and the product was the main peak. The reaction solution was cooled to room temperature, silica gel was added, and column chromatography was used for purification to obtain compound 127 (white solid, 100 mg, yield 32%).

[0203] 5. Synthesis of compound 164

[0204] In a 100 mL single-neck flask, compound 4-5 (250 mg, 0.51 mmol), compound 164-1 (212 mg, 1.03 mmol) and cesium fluoride (156 mg, 1.03 mol) were added to 20 mL of 1,4-dioxane and 2 mL of water, N2was replaced once, PdCl2(dppf) (51 mg, 62.3 μmol) was added, N2was replaced three times, and the temperature was directly raised to 100°C and stirred overnight. LC-MS monitoring showed that the product was the main peak, and silica gel powder was added for sample mixing. The organic phase was purified by silica gel column chromatography to obtain compound 164 (50 mg, yellow solid, yield 18.1%).

[0205] Biological activity evaluation (insecticidal activity test)

[0206] Spodoptera frugiperda, Mythima separata, Helicoverpa armigera: The original drug was diluted with acetone to prepare gradient concentrations; 3-4 pieces of host plant leaves (young corn leaves) without insecticide and without insect-resistant genes were picked and cut into 3-4 cm long leaves, then placed in a 9 cm diameter plastic box, 10 starved for 2 hours Test insects were inserted, and a spray tower was used for spraying. Repeat 3 times, with the highest dose of acetone as a control. After spraying, cover the box tightly and place it in the treatment room (temperature 25°C, humidity 60%). Investigate the number of dead insects after 48 hours, calculate the mortality rate, and representative data are shown in Table 3. Mortality rate = (number of dead insects / number of test insects) x 100%

[0207] Table 3 Insecticidal activity test results (2DAA) Note: N means no data.

[0208] 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, helicoverpa armigera, cotton bollworm, grass caterpillar, 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. Allium calyptrata, etc.), Coleoptera (e.g. yellow curve jumping beetle, small ape leaf beetle, etc.), and thrips (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 characteristics such as broad spectrum, high efficiency and strong systemicity, but also can effectively control resistant pests and have certain commercial value.

Claims

1. A fused heterocyclic compound, as shown in general formula I: wherein X represents a cycloalkyl group, an aryl group or a heterocyclic group; R1, R2, R3, R4, R5, independently, represent hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, cycloalkyl, aryl, heterocyclyl, -OR 21 , -SR 21 , -SOR 21 , -(SO2)R 21 , -N(R 21 )2, -O(CO)R 21 , -O(CO)OR 21 , -(CO)R 21 , -(CO)OR 21 or -(CO)N(R 21 )2; said alkyl, alkenyl or alkynyl is optionally substituted with at least one radical selected from halogen, cyano, nitro, cycloalkyl, aryl, heterocyclyl, -OR 21 , -SR 21 , -SOR 21 , -(SO2)R 21 , -N(R 21 )2, -O(CO)R 21 , -O(CO)OR 21 , -(CO)R 21 or -(CO)N(R 21 )2; R 21 are each independently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, aryl, heterocyclyl, aralkyl, or heterocyclylalkyl; the aforementioned "cycloalkyl group", "heterocyclic group" or "aryl group" is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R, or two adjacent carbon atoms of the ring form a fused ring with -CH2CH2CH2-, -CH2CH2CH2CH2-, -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with halogen; R independently represents hydrogen, alkyl, alkenyl, alkynyl, alkyl, alkenyl or alkynyl substituted with at least one group selected from halogen, hydroxy, cyano or alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl or phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

2. The fused heterocyclic compound according to claim 1, wherein X represents a C3-C8 cycloalkyl group, an aryl group or a heterocyclic group; R1, R2, R3, R4, R5represent, independently from each other, hydrogen, halogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, cyano, nitro, C3-C8cycloalkyl, aryl, heterocyclyl, -OR 21 , -SR 21 , -SOR 21 , -(SO2)R 21 , -N(R 21 )2, -O(CO)R 21 , -O(CO)OR 21 , -(CO)R 21 , -(CO)OR 21 or -(CO)N(R 21 )2; said C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl being optionally substituted by at least one radical chosen from halogen, cyano, nitro, C3-C8cycloalkyl, aryl, heterocyclyl, -OR 21 , -SR 21 , -SOR 21 , -(SO2)R 21 , -N(R 21 )2, -O(CO)R 21 , -O(CO)OR 21 , -(CO)R 21 or -(CO)N(R 21 )2; R 21 are each independently hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, aryl, heterocyclyl, arylC1-C8alkyl, or heterocyclylC1-C8alkyl; the aforementioned "C3-C8 cycloalkyl group", "heterocyclic group" or "aryl group" is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R, or two adjacent carbon atoms of the ring form a fused ring with -CH2CH2CH2-, -CH2CH2CH2CH2-, -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with halogen; R independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl substituted with at least one group selected from halogen, hydroxy, C1-C8 alkoxy, cyano or C1-C8 alkoxycarbonyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, phenyl or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, haloC1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or haloC1-C8 alkoxy.

3. The fused heterocyclic compound according to claim 1 or 2, wherein X represents a C3-C6 cycloalkyl group, an aryl group or a heterocyclic group; R1, R2, R3, R4, R5represent, independently from each other, hydrogen, halogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, cyano, nitro, C3-C6cycloalkyl, aryl, heterocyclyl, -OR 21 , -SR 21 , -SOR 21 , -(SO2)R 21 , -N(R 21 )2, -O(CO)R 21 , -O(CO)OR 21 , -(CO)R 21 , -(CO)OR 21 or -(CO)N(R 21 )2; said C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl is optionally substituted with at least one radical chosen from halogen, cyano, nitro, C3-C6cycloalkyl, aryl, heterocyclyl, -OR 21 , -SR 21 , -SOR 21 , -(SO2)R 21 , -N(R 21 )2, -O(CO)R 21 , -O(CO)OR 21 , -(CO)R 21 or -(CO)N(R 21 )2; R 21 are each independently hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, haloC1-C6alkyl, haloC2-C6alkenyl, haloC2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, aryl, heterocyclyl, arylC1-C6alkyl, or heterocyclylC1-C6alkyl; The aforementioned "C3-C6-cycloalkyl", "heterocyclyl" or "aryl" is optionally substituted by at least one radical selected from the group consisting of oxo, halogen, cyano, nitro, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, halogen-C1-C6-alkyl, halogen-C2-C6-alkenyl, halogen-C2-C6-alkynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R, or two adjacent carbon atoms of the ring form a fused ring with -CH2CH2CH2-, -CH2CH2CH2CH2-, -OCH2CH2- or -OCH2O- which is unsubstituted or substituted by halogen; R independently from each other represents hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl substituted by at least one radical selected from the group consisting of halogen, hydroxy, C1-C6-alkoxy, cyano or C1-C6-alkoxycarbonyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C3-C6-cycloalkenyl, C3-C6-cycloalkenyl-C1-C6-alkyl, phenyl or phenyl substituted by at least one radical selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, halogen-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylsulfonyl, C1-C6-alkoxy or halogen-C1-C6-alkoxy; Preferably, the compound is selected from any one of Table 1.

4. A process for the preparation of a condensed heterocyclic compound according to any one of claims 1 to 3, characterized in that, comprising the following steps: The compound of formula I is prepared by reacting a compound of formula II with a compound of formula III, according to the following reaction scheme: wherein either Q1or Q2is halogen and the other is R1, R2, R3, R4, R5 and X are as defined in any one of claims 1 to 3; Preferably, the reaction is carried out in the presence of a solvent; more preferably, a base and a catalyst are added during the reaction; further preferably, the base is selected from at least one of an inorganic base or an organic base; the catalyst is selected from at least one of Pd(dppf)Cl2, Pd(dppf)Cl 2. CH2Cl2, Pd(OAc)2, PdCl2, Pd(PPh3)4or PdCl2(PPh3)2; and / or the solvent is an organic solvent / water, the organic solvent being preferably at least one of an aromatic hydrocarbon, DMF, DMA, THF, acetonitrile, methanol, ethanol, isopropanol, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate.

5. An insecticide composition, characterized by, comprising an insecticidally effective amount of at least one of the fused heterocyclic compounds of any one of claims 1 to 3; preferably, further comprising a formulation adjuvant; more preferably, further comprising another active ingredient.

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

7. Use of the fused heterocyclic compound of any one of claims 1 to 3 or the composition of claim 5 for controlling pests.

8. An intermediate of formula II as shown in claim 4.

9. A process for preparing a compound of formula I as shown in claim 1, comprising the following steps:

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