Substituted benzisoxazole compound and preparation method therefor, insecticidal composition, and use

Abstract

The present invention relates to the technical field of pesticides, and in particular relates to a substituted benzisoxazole compound and a preparation method therefor, an insecticidal composition, and a use. The compound is represented by general formula (I), where Z1, Z2, Z3, Z4, and Z5 independently represent N or CR, R independently represents hydrogen, halogen, alkyl, alkenyl, etc., X represents alkyl, haloalkyl, alkenyl, etc., and Y represents alkyl. The compound has excellent control efficacy against pests such as Spodoptera frugiperda, Mythimna separata, Plutella xylostella, and Spodoptera litura.

Description

Substituted benzisoxazole compound, preparation method thereof, insecticidal composition and application TECHNICAL FIELD

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

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

[0003] The present application provides a substituted benzisoxazole compound, a preparation method thereof, an insecticidal composition and application, which has excellent insecticidal activity against pests such as Spodoptera frugiperda, Mythimna separata, Plutella xylostella and Spodoptera litura.

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

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

[0006] Z1, Z2, Z3, Z4 and Z5 independently represent N or CR;

[0007] R independently represents hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, -SF5, -OR 10 , S(O) m R 10 , -N(R 10 )2, -(CO)R 10 , -(CO)OR 10 , cycloalkyl, aryl or heterocyclyl; wherein the alkyl, alkenyl or alkynyl is optionally substituted with at least one group selected from halogen, trialkylsilyl, -OR 10 , -S(O) m R 10 , cycloalkyl, heterocyclyl or aryl;

[0008] X represents alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, -N(R 10 )2, cycloalkyl, cycloalkylalkyl, aryl, heterocyclyl, arylalkyl or heterocyclylalkyl;

[0009] Y represents alkyl;

[0010] R 10 each independently represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, aryl, or arylalkyl;

[0011] m represents 0, 1 or 2;

[0012] the aforementioned "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 11 , -SR 11 , -(CO)R 11 , -(CO)OR 11 , -(CO)N(R 11 )2, -(CS)N(R 11 )2, -(SO)R 11 , or -(SO2)R 11 ; or two adjacent carbon atoms in the ring form a fused ring with -OCH2O-, -CH2CH2CH2O-, or -CH=CHCH=CH- which is unsubstituted or substituted with halogen; or one saturated carbon atom in the ring is connected with both ends of -OCH2CH2O- which is unsubstituted or substituted with halogen to form a ring structure;

[0013] R 11 each independently represents hydrogen, alkyl, haloalkyl, phenyl, or phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy.

[0014] Preferably, R independently represents hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, -SF5, -OR 10 , -S(O) m R 10 , -N(R 10 )2, -(CO)R 10 , -(CO)OR 10 , C3-C8 cycloalkyl, aryl, or heterocyclyl; wherein C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl is optionally substituted with at least one group selected from halogen, tri C1-C8 alkylsilyl, -OR 10 , -S(O) m R 10 , C3-C8 cycloalkyl, heterocyclyl, or aryl;

[0015] X represents C1-C8alkyl, haloC1-C8alkyl, C2-C8alkenyl, haloC2-C8alkenyl, C2-C8alkynyl, haloC2-C8alkynyl, -N(R 10 )2, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, aryl, heterocyclyl, arylC1-C8alkyl or heterocyclylC1-C8alkyl;

[0016] Y represents C1-C8alkyl;

[0017] R 10 each independently represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, heterocyclyl, heterocyclylC1-C8alkyl, aryl or arylC1-C8alkyl;

[0018] The aforementioned "C3-C8cycloalkyl", "heterocyclyl" or "aryl" is optionally substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl, -OR 11 , -SR 11 , -(CO)R 11 , -(CO)OR 11 , -(CO)N(R 11 )2, -(CS)N(R 11 )2, -(SO)R 11 or -(SO2)R 11 ; or two adjacent carbon atoms in the ring form a fused ring with -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH- which is unsubstituted or substituted by halogen; or one saturated carbon atom in the ring is linked to both ends of -OCH2CH2O- which is unsubstituted or substituted by halogen;

[0019] R 11 each independently represents hydrogen, C1-C8alkyl, haloC1-C8alkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8alkyl, haloC1-C8alkyl, C1-C8alkoxycarbonyl, C1-C8alkylthio, C1-C8alkylsulfonyl, C1-C8alkoxy or haloC1-C8alkoxy.

[0020] More preferably, R independently represents hydrogen, halogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, cyano, nitro, -SF5, -OR 10 , -S(O)m R 10 、-N(R 10 )2、-(CO)R 10 、-(CO)OR 10 , C3-C6 cycloalkyl, aryl or heterocyclic group; wherein, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally selected from halogen, tri-C1-C6 alkylsilyl, -OR 10 、-S(O) m R 10 , C3-C6 cycloalkyl, heterocyclic group or aryl group;

[0021] X represents C1-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, -N(R 10 )2, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, aryl, heterocyclyl, arylC1-C6 alkyl or heterocyclylC1-C6 alkyl;

[0022] Y represents a C1-C6 alkyl group;

[0023] R 10 Each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, aryl or arylC1-C6 alkyl;

[0024] The aforementioned "C3-C6 cycloalkyl", "heterocyclyl" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, -OR 11 、-SR 11 、-(CO)R 11 、-(CO)OR 11 、-(CO)N(R 11 )2、-(CS)N(R 11 )2、-(SO)R 11 or -(SO2)R 11 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH-; or a saturated carbon atom on the ring is connected to both ends of unsubstituted or halogen-substituted -OCH2CH2O- to form a ring structure;

[0025] R 11 independently of each other represent hydrogen, C1-C6alkyl, halogenated C1-C6alkyl, phenyl or phenyl substituted by at least one radical selected from the group consisting of halogen, cyano, nitro, C1-C6alkyl, halogenated C1-C6alkyl, C1-C6alkyloxycarbonyl, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkyloxy or halogenated C1-C6alkyloxy.

[0026] In one embodiment, Z1, Z2, Z3, Z4, Z5 independently represent N or CR, and contain at most two N (no N, 1 N or 2 N).

[0027] In another embodiment, Z1 represents N, Z2 represents CR1, Z3 represents CR2, Z4 represents CR3, Z5 represents N; R1, R2, R3 independently represent hydrogen, halogen, alkyl, halogenated alkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cyano, nitro, -OR 10 , -alkylene-OR 10 , -S(O) m R 10 , -alkylene-S(O) m R 10 , cycloalkyl, cycloalkylalkyl, aryl, heterocyclyl, arylalkyl or heterocyclylalkyl. Preferably, R1, R2, R3 independently represent hydrogen, halogen, C1-C8alkyl, halogenated C1-C8alkyl, C2-C8alkenyl, halogenated C2-C8alkenyl, C2-C8alkynyl, halogenated C2-C8alkynyl, cyano, nitro, -OR 10 , -(C1-C8alkylene)-OR 10 , -S(O) m R 10 , -(C1-C8alkylene)-S(O) m R 10 , C3-C8cycloalkyl, C3-C8cycloalkyl C1-C8alkyl, aryl, heterocyclyl, aryl C1-C8alkyl or heterocyclyl C1-C8alkyl. More preferably, R1, R2, R3 independently represent hydrogen, halogen, C1-C6alkyl, halogenated C1-C6alkyl, C2-C6alkenyl, halogenated C2-C6alkenyl, C2-C6alkynyl, halogenated C2-C6alkynyl, cyano, nitro, -OR 10 , -(C1-C6alkylene)-OR 10 , -S(O) m R 10 , -(C1-C6alkylene)-S(O) m R 10C3-C6cycloalkyl, C3-C6cycloalkylCi-C6alkyl, aryl, heterocyclyl, arylCi-C6alkyl, or heterocyclylCi-C6alkyl.

[0028] In the definitions of the compounds of the general formulae described above and in all the formulae below, the professional terms used, whether used alone or in a compound word, stand for the following substituents: Alkyl groups having more than two carbon atoms can be straight-chained or branched. As in the compound word "alkylene-OR 10 " the alkylene can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. Alkyl groups are, for example, C1alkyl - methyl; C2alkyl - ethyl; C3alkyl - propyl, such as n-propyl or isopropyl; C4alkyl - butyl, such as n-butyl, isobutyl, tert-butyl or 2-butyl; C5alkyl - pentyl, such as n-pentyl; C6alkyl - hexyl, such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, alkenyl is, for example, ethenyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl. Alkynyl is, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. The multiple bonds can be in any position of each unsaturated group. Cycloalkyl is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl group having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, wherein the double bond can be in any position. Halogen is fluorine, chlorine, bromine or iodine.

[0029] Unless specifically indicated otherwise, "aryl" as used herein includes, but is not limited to, phenyl, naphthyl, " Heterocyclyl" as used herein includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups " Heterocyclyl" as used herein includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups

[0030] The term "optionally" or "optional" means that the subsequently described event or circumstance can or can not occur, and thus that the description includes instances where the event or circumstance occurs and instances where it does not. For example, the term "optionally substituted" means that the specified atom or group is either unsubstituted or substituted with one or more substituents. If a group is substituted with a group, this is to be understood as meaning that the group is substituted with one or more, identical or different, groups selected from those mentioned. In addition, the same or different substituents contained in the same or different substituents are each selected independently of one another, either identically or differently. This also applies to ring systems formed by different atoms and elements. At the same time, the scope of the claims is to exclude those compounds which are chemically unstable under standard conditions, as known to the person skilled in the art.

[0031] In addition, unless specifically limited otherwise, the term "substituted" as used herein means substituted with one, two, three, four, or five groups; groups (including heterocyclyl, aryl, etc.) not marked with a specific attachment position can be attached at any position, including the position attached to C or N; if it is substituted, the substituents can also be substituted at any position, as long as the rules of chemical bond connection are met. For example, a heteroaryl group substituted with 1 methyl group may represent , etc.

[0032] If various functional groups are present, the present application also includes any keto and enol tautomer forms and mixtures and salts thereof.

[0033] The present application provides a substituted benzisoxazole compound having a chiral center as shown in formula I':

[0034] wherein the carbon atom at position * is a chiral center, and the definitions of substituents Z1, Z2, Z3, Z4, Z5, X and Y are as described above;

[0035] has a stereochemical purity of 60-100% (S), preferably 70-100%, more preferably 80-100%, further preferably 90-100%, and more further preferably 95-100%, based on the content of stereoisomers having R and S configurations at position *; or has a stereochemical purity of 60-100% (R), preferably 70-100%, more preferably 80-100%, further preferably 90-100%, and more further preferably 95-100%, based on the content of stereoisomers having R and S configurations at position *.

[0036] wherein "stereochemical purity" refers to the amount of the stereoisomer as a percentage of the total amount of stereoisomers having a chiral center that is generated.

[0037] In the present application, the stereochemical configuration at the position * in formula I' is determined according to the Cahn-Ingold-Prelog system, however the subject matter of the present application also relates to all stereoisomers of other positions included in formula I, and mixtures thereof. Such compounds of formula I include, for example, one or more additional asymmetric carbon atoms or other double bonds not specifically indicated in formula I. It is to be understood that the present application includes pure isomers and mixtures of isomers enriched to varying degrees, for example, the asymmetric carbon atom at the position * is in the R configuration or the S configuration, or in mixtures, the compounds or likewise configured compounds have the R configuration or the S configuration at the position *, or are present in proportions in which the compounds having the R configuration or the S configuration predominate (at least 60% of the configuration), while the other asymmetric carbon atoms can be present in racemic form, or can also be resolved to varying degrees. As long as the stereochemical configuration is met, possible stereoisomers defined by the particular spatial form, such as enantiomers, diastereomers, Z- and E-isomers, are included in formula I and can be obtained from mixtures of stereoisomers in a conventional manner, or can also be prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.

[0038] The method for preparing the substituted benzisoxazole compound comprises the following steps:

[0039] (1) preparing the compound of formula I from the compound of formula II under acidic conditions, as shown in the following reaction equation:

[0040] or (2) preparing the compound of formula I from the reaction of the compound of formula III and the compound of formula IV, as shown in the following reaction equation:

[0041] or (3) preparing the compound of formula I from the reaction of the compound of formula V and the compound of formula VI, as shown in the following reaction equation:

[0042] wherein, in Q1 and Q2, either is halogen (preferably chlorine) and the other is in Q3 and Q4, either is SR 21 and the other is R 21 C1-C6 alkyl or phenyl; Z1, Z2, Z3, Z4, Z5, X and Y are as defined above.

[0043] In one specific embodiment, the reaction (1) is carried out in the presence of an acid and a solvent.

[0044] In another embodiment, the acid is selected from at least one of inorganic acids (such as HC1, HBr, HI, H2S04, H2S03, H2C03, HN03, H3P04, H3P03, H2S, etc.) or organic acids (such as formic acid, acetic acid, propionic acid, benzoic acid, p-toluene sulfonic acid, etc.).

[0045] In another embodiment, the solvent is selected from at least one of aromatic hydrocarbons (such as benzene, chlorobenzene or toluene), DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate.

[0046] In one embodiment, the reaction (2) is carried out in the presence of a base, a catalyst and a solvent.

[0047] In another embodiment, the base is selected from at least one of inorganic bases (such as K2C03, Na2C03, Cs2C03, NaHC03, KF, CsF, KI, Nal, KOAc, AcONa, K3P04, t-BuONa, EtONa, NaOH, KOH, NaOMe, NaH, KH, etc.) or organic bases (such as DMAP, pyrazole, triethylamine, DIEA, etc.).

[0048] In another embodiment, the catalyst is selected from at least one of Pd(dppf)Cl2, Pd(OAc)2, PdC12, or 1,1'-bis(diphenylphosphino)ferrocene palladium(II) dichloride dichloromethane complex.

[0049] In another embodiment, the solvent is an organic solvent / water, the organic solvent is selected from at least one of aromatic hydrocarbons, DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate.

[0050] In one embodiment, the reaction (3) is carried out in the presence of cuprous thiophene-2-carboxylate, a catalyst and a solvent.

[0051] In another embodiment, the catalyst is selected from at least one of Pd(dppf)Cl2, Pd(OAc)2, PdC12, or Pd(PPh3)4 or 1,1'-bis(diphenylphosphino)ferrocene palladium(II) dichloride dichloromethane complex.

[0052] In another embodiment, the solvent is selected from at least one of aromatic hydrocarbons (such as benzene, chlorobenzene or toluene), DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate.

[0053] In one embodiment, the compound of Formula II is prepared from a compound of Formula VII and a compound of Formula VIII, according to the following reaction scheme:

[0054] wherein M is OH or halogen.

[0055] In one embodiment, the reaction is carried out in the presence of a solvent.

[0056] In another embodiment, a condensing agent and / or a base is added during the reaction.

[0057] In one 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.).

[0058] In one embodiment, the condensing agent is selected from at least one of Py-BOP, Py-AOP, EDCI, HOBT, DCC, HBTU or HATU.

[0059] In one embodiment, the solvent is selected from at least one of aromatic hydrocarbons (such as benzene, chlorobenzene or toluene), DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate.

[0060] In addition, the compound of Formula I can be prepared according to the methods disclosed in CN201780006638.8, CN202280017806.4, etc.

[0061] The present application also provides an intermediate, which is a compound of Formula II.

[0062] Suitable salts of the compounds according to the application according to the 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 tolerated. 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 salts, dicyclohexylammonium salts, N,N'-dibenzylethylenediammonium salts, pyridinium salts, picolinium salts or ethanolammonium salts; salts with inorganic acids (for example hydrochlorides, hydrobromides, dihydrogen sulphates, trihydrogen sulphates or phosphates); salts with organic carboxylic acids or organic sulphonic acids (for example formates, acetates, trifluoroacetates, maleates, tartrates, methanesulphonates, benzenesulphonates or 4-toluenesulphonates). It is known that tertiary amines such as some of the compounds according to the application are capable of forming N-oxides, which are likewise salts according to the application.

[0063] 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 mixtures of the corresponding isomers in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The present application therefore includes pure stereoisomers as well as any mixtures of these isomers.

[0064] The present application also relates to a method for controlling animal pests, wherein a compound of the formula I can act on the animal pests and / or their habitat. The control of the animal pests is preferably carried out in agriculture and forestry, and in the protection of materials. Excluded from the method are preferably methods of surgical treatment and therapeutic treatment of the human or animal body and diagnostic methods which are carried out on the human or animal body.

[0065] The present application also relates to the use of a compound of the formula I as a pesticide, in particular as a crop protection agent.

[0066] In the context of the present application, the term "pesticide" also generally includes the term "crop protection agent".

[0067] Compounds of formula I which have good plant tolerance, favourable homeotherm toxicity and good environmental compatibility are suitable for protecting plants and plant organs, for increasing the harvest yields, for improving the quality of the harvested material and for controlling animal pests, in particular insects, arachnids, myriapods, nematodes and molluscs, in agriculture, in horticulture, in livestock farming, in poultry farming, in fish farming, in forestry, in gardens and leisure facilities, for the protection of stored products and materials and for the protection in the hygiene sector. These compounds are preferably used as insecticides. They can be active against normally sensitive and resistant species and against all or some stages of development. The aforementioned pests include, but are not limited to, pests from the phylum Arthropoda, especially from the class of the Arachnida, from the class of the Chilopoda, from the order of the Collembola, from the class of the Diplopoda, from the class of the Insecta, from the order of the Coleoptera, from the order of the Diptera, from the order of the Heteroptera, from the order of the Homoptera, from the order of the Hymenoptera, from the order of the Isopoda, from the order of the Isoptera, from the order of the Lepidoptera, from the order of the Orthoptera or Saltatoria, from the order of the Phthiraptera, from the order of the Psocoptera, from the order of the Siphonaptera, from the order of the Thysanoptera, from the order of the Zygentoma (= Thysanura), from the class of the Symphyla, from the phylum of the Mollusca, and from the class of the Gastropoda.

[0068] At certain concentrations and application rates, the compounds of formula I can also optionally be used as insecticides, safeners, growth regulators or agents for improving plant properties, as fungicides and gametocides, for example as fungicides, antimycotics, bactericides, viricides (including antiviroid agents) or as agents against MLO (Mycoplasma-like organisms) and RLO (Rickettsiaceae-like organisms). If appropriate, they can also be used as intermediates or precursors for the synthesis of other active ingredients.

[0069] The present application also relates to formulations comprising at least one compound of the formula I and to the use thereof as a pesticidal application form, such as drenches, drip and spray liquids, prepared therefrom. In certain cases, the application forms comprise further pesticides and / or adjuvants having an improved action, such as penetrants, for example vegetable oils (such as rapeseed oil, sunflower oil), mineral oils (such as paraffin oil), alkyl esters of vegetable fatty acids (such as rapeseed oil methyl ester or soybean oil methyl ester), or alkanol alkoxylates; and / or spreaders, for example alkylsilicones and / or salts (such as organic or inorganic ammonium or phosphonium salts, for example ammonium sulfate or di-ammonium hydrogenphosphate); and / or retention promoters, for example dioctyl sulfosuccinate or hydroxypropyl guar polymer; and / or wetters, for example glycerol; and / or fertilizers, for example ammonium-, potassium- or phosphorus-containing fertilizers.

[0070] 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.

[0071] These are preferably formulations or application forms which comprise auxiliaries, such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners; and or further auxiliaries, such as adjuvants. In the present context, an adjuvant is a component which enhances the biological efficacy of the formulation, whereas the component itself does not have any biological efficacy. Examples of adjuvants are agents which promote retention, spreading, adhesion to the leaf surface or penetration.

[0072] The formulations are prepared in known manner, for example by mixing the compound of the formula I with auxiliaries, such as extenders, solvents and / or solid carriers and / or further auxiliaries such as surfactants. The formulations are prepared immediately before use or during use.

[0073] The adjuvants used can be substances which are suitable for imparting particular properties to the formulations of the compounds of the formula I or to the use forms prepared from these formulations, such as ready-to-use insecticide sprays, such as spray liquors or seed dressing products, for example particular physical, technical and / or biological properties.

[0074] Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example selected from the group consisting of aromatic or aliphatic hydrocarbons, such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes, alcohols and polyols which can also be optionally substituted, etherified and / or esterified, ketones, such as acetone, cyclohexanone, esters, including fatty and oil, and (poly)ethers, unsubstituted and substituted amines, amides, lactams, such as N-alkylpyrrolidones, and lactones, sulfones and sulfoxides, such as dimethyl sulfoxide.

[0075] If the extender used is water, it is also possible to use, for example, organic solvents as cosolvents. Useful liquid solvents are mainly: aromatic compounds, such as xylene, toluene or alkylnaphthalenes; chlorinated aromatic and aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or dichloromethane; aliphatic hydrocarbons, such as cyclohexane or paraffins, such as mineral oil fractions, mineral and vegetable oils; alcohols, such as butanol or glycol and ethers and esters thereof; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strongly polar solvents, such as dimethylformamide, dimethylacetamide and dimethyl sulfoxide and water.

[0076] In principle, all suitable solvents can be used. Examples of suitable solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes; chlorinated aromatic or aliphatic hydrocarbons, such as chlorobenzene, chloroethylene, dichloromethane; aliphatic hydrocarbons, such as cyclohexane, paraffins, mineral oil fractions, mineral and vegetable oils; alcohols, such as methanol, ethanol, isopropanol, butanol or glycol and ethers and esters thereof; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strongly polar solvents, such as dimethyl sulfoxide and water.

[0077] In principle, all suitable carriers can be used. Useful carriers include, inter alia, for example, ammonium salts and ground natural minerals, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomite; and ground synthetic materials, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used. Useful carriers for granules include, for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite; and synthetic granules of inorganic and organic powders; and granules of organic materials, such as sawdust, paper, coconut shells, corn cobs and tobacco stems.

[0078] Also liquid gaseous extenders or solvents can be used. Particularly suitable extenders or carriers are those which are gaseous at ambient temperature and atmospheric pressure, for example aerosol propellant gases such as halogenated hydrocarbons, and also butane, propane, nitrogen and carbon dioxide.

[0079] Examples of emulsifiers and / or foaming, dispersing or wetting agents, or mixtures of these surfactants, having ionic or non-ionic properties, are salts of polyacrylic acids, salts of lignosulphonic acids, salts of phenolsulphonic acids or naphthalenesulphonic acids, polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty amines or substituted phenols, preferably alkylphenols or arylphenols, salts of sulphosuccinic esters, taurine derivatives, preferably alkyl taurates, phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of compounds containing sulphates, sulphonates and phosphates, for example alkyl aryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, protein hydrolysates, lignosulphite waste liquors and methylcellulose. If one of the above compounds of the formula I and / or one of the above inert carriers is not water-soluble and application is carried out in water, the presence of a surfactant is advantageous.

[0080] Other auxiliaries which can be present in the formulations and in the use forms derived from them include colourants such as inorganic pigments, for example iron oxide, titanium oxide, Prussian Blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and also nutrients and micronutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

[0081] The additional components can be stabilisers which improve chemical and / or physical stability, for example cold-stabilisers, preservatives, antioxidants, light stabilisers or other agents. Foaming and de-foaming agents can also be present.

[0082] Furthermore, the formulations and use forms derived from them can also comprise, as additional auxiliaries, sticking agents such as carboxymethylcellulose, and also natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyacrylic acid, or natural phospholipids, such as cephalins, lecithins and synthetic phospholipids. Further possible auxiliaries are mineral and vegetable oils.

[0083] Optionally, other auxiliaries can be present in the formulations and in the use forms derived from them. Examples of such additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic agents, penetration agents, retention aids, stabilisers, sequestering and chelating agents, complexing agents, humectants and spreaders. In general, the compounds of the formula I can be combined with any solid or liquid additive which is customary for formulation purposes.

[0084] Useful retention promoters include all those substances which lower the kinetic surface tension, such as dioctyl sulfosuccinate; or all those substances which increase the viscoelasticity, such as hydroxypropyl guar polymers.

[0085] In the context of the present application, useful penetration agents include all those substances which are typically used to enhance the penetration of active agrochemical 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 di-ammonium hydrogenphosphate.

[0086] The formulations preferably comprise from 0.00000001 to 98% by weight of the compound of formula I, more preferably from 0.01 to 95% by weight of the compound of formula I, most preferably from 0.5 to 90% by weight of the compound of formula I, based on the weight of the formulation.

[0087] The content of the compound of formula I in the use forms prepared from the formulations, especially the insecticides, can vary within wide ranges. The concentration of the compound of formula I in the use forms can generally be from 0.00000001 to 95% by weight of the compound of formula I, preferably from 0.00001 to 1% by weight, based on the weight of the use form. Application is carried out in the customary manner appropriate for the use form.

[0088] The compound of formula I can also be used in combination with one or more substances selected from the group consisting of suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbicides, beneficial organisms, pesticides, fertilizers, bird repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators, in order to broaden the spectrum of action, for example, to prolong the duration of action, to increase the rate of action, to prevent repellence or to prevent the development of resistance. In addition, such active ingredient combinations can improve plant growth and / or tolerance to abiotic factors, such as high or low temperatures, drought or high water content or soil salinity. It is also possible to improve flowering and fruiting performance, to optimize germination capacity and root development, to facilitate harvesting and to increase yield, to influence ripening, to improve the quality and / or nutritional value of the harvested products, to prolong the storage period and / or to improve the processing properties of the harvested products.

[0089] In addition, the compounds of the formula I can be present in mixtures with other active ingredients or semiochemicals such as attractants and / or bird repellents and / or plant activators and / or growth regulators and / or fertilizers. Likewise, the compounds of the formula I can be used in the form of mixtures with agents for improving the properties of plants such as growth, yield and quality of the harvested material.

[0090] 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.

[0091] 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.

[0092] Insecticides / acaricides / nematicides

[0093] The active ingredients mentioned herein by their "common names" are known and are described, for example, in The Pesticide Manual, 16th Edition, British Crop Protection Council 2012, or can be retrieved on the internet (for example http: / / www.alanwood.net / pesticides). th

[0094] ​(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.

[0095] (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.

[0096] (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 (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)isomers], tralomethrin, and transfluthrin; or DDT; or methoxychlor.

[0097] (4) Nicotinic acetylcholine receptor (nAChR) agonists, for example neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor.

[0098] (5) Allosteric activators of nicotinic acetylcholine receptors (nAChR), such as spinosyns, such as spinetoram and spinosad.

[0099] (6) Chloride channel activators, for example, avermectins / milbemycins, such as abamectin, emamectin benzoate, lepimectin and milbemectin.

[0100] (7) Juvenile hormone mimetics, for example, juvenile hormone analogs such as hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

[0101] (8) Active ingredients with unknown or nonspecific mechanisms of action, e.g.

[0102] Alkyl halides, such as methyl bromide and other alkyl halides; or chloropicrine or sulfuryl fluoride or borax or tartar emetic.

[0103] (9) selective feeding blockers, such as pymetrozine or fionicamid.

[0104] (10) mite growth inhibitors, such as clofentezine, hexythiazox and diflovidazin or etoxazole.

[0105] (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.

[0106] (12) oxidative phosphorylation inhibitors, ATP disruptors, such as diafenthiuron or organotin compounds, such as azocyclotin, cyhexatin and fenbutatin oxide or propargite or tetradifon.

[0107] (13) oxidative phosphorylation decouplers interrupting the H+ gradient, such as chlorfenapyr, DNOC and sulfluramid.

[0108] (14) nicotinic acetylcholine receptor agonists, such as bensultap, cartap hydrochloride, thiocyclam and thiosultap-sodium.

[0109] (15) Inhibitors of chitin biosynthesis, type 0, for example bistrifluron, chlofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

[0110] (16) Inhibitors of chitin biosynthesis, type 1, for example buprofezin.

[0111] (17) Moulting disruptor (especially for Diptera, i.e. flies), for example cyromazine.

[0112] (18) Ecdysone receptor agonists, for example chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0113] (19) Octopaminergic agonists, for example amitraz.

[0114] (20) Complex-III electron transport inhibitors, for example hydramethylnone, or acequinocyl, or fluacrypyrim.

[0115] (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.).

[0116] (22) Voltage-gated sodium channel blockers, for example indoxacarb or metaflumizone.

[0117] (23) Inhibitors of acetyl-CoA carboxylase, for example tetronic and tetramic acid derivatives, such as spirodiclofen, spiromesifen and spirotetramat.

[0118] (24) Complex-IV electron transport inhibitors, for example phosphines, such as aluminium phosphide, calcium phosphide, phosphine and zinc phosphide; or cyanides.

[0119] (25) Complex-II electron transport inhibitors, for example cyenopyrafen and cyflumetofen.

[0120] (28) Ryanodine receptor effectors, for example diamides, such as chlorantraniliprole, cyantraniliprole and flubendiamide;

[0121] 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 benzylamide (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),

[0122] fungicides

[0123] 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).

[0124] (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.

[0125] (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) diclocymet, (2.31) fenoxanil, (2.32) fluazinam, (2.33) metrafenone, (2.34) tolylfluron, (2.35) N-[9-(dichloromethyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.36) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.37) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.38) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.39) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.40) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.41) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.42) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.43) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.44) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.45) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.46) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.47) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.48) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.49) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.50) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.51) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.52) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.53) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.54) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.55) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.56) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.57) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.58) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.59) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.60) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.61) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.62) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.63) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.64) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.65) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.66) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanesulfonamide, (2.67) N-[9-(2,6-dichlorobenzoyl)-9H-purin-6-yl]-N-methyl- methanes30) 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.

[0126] (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.

[0127] (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.

[0128] (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.

[0129] (6) Resistance inducers, for example (6.1) acibenzolar-S-methyl, (6.2) isotianil, (6.3) probenazole, (6.4) tiadinil and (6.5) laminarin.

[0130] (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.

[0131] (8) Inhibitors of the ATP production, for example (8.1) fentin acetate, (8.2) fentin chloride, (8.3) fentin hydroxide, (8.4) silthiofam.

[0132] (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.

[0133] (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.

[0134] (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-1-[(4-methylbenzoyl)amino]butan-2-yl} carbamate;

[0135] (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.

[0136] (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;

[0137] (14) decouplers, for example (14.1) binapacryl, (14.2) dinocap, (14.3) ferimzone, (14.4) fluazinam and (14.5) meptyldinocap.

[0138] (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) bifenazate, (15.71) chlor- benzoilate, (15.72) cloquintocet, (15.73) cyflumetofen, (15.74) cyenopyrafen, (15.75) diafenthiuron, (15.76) etoxazole, (15.77) fenoxasulfone, (15.78) flubendiamide, (15.79) flufenerim, (15.80) fluten-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.

[0139] Biological pesticides as mixed components

[0140] The compounds of the formula I can be combined with biological pesticides.

[0141] Biological pesticides include, inter alia, bacteria, fungi, yeasts, plant extracts and products of microbial origin, including proteins and secondary metabolites.

[0142] Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria which act as bioinsecticides, biofungicides or bionematicides.

[0143] 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.

[0144] Safety agents as mixed components

[0145] The compounds of the formula I can be combined with safeners, such as 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} sulfonamide (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).

[0146] Plants and plant parts

[0147] 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 and plants that occur in the wild, whether cultivated or not, and also plants that are cultivated, 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 apples, pears, citrus fruits and grapes). The crop plants can be plants that have been obtained by conventional methods of breeding and optimization or by biotechnological and genetic engineering methods or a combination of these methods, including transgenic plants and plant cultivars, which are protected by plant breeders’ rights and which are not protected by plant breeders’ rights. 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.

[0148] 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.

[0149] 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 as meaning individual organs, as well as groups or collections of organs, of a plant. Preferably, the term "parts" is to be understood as meaning leaves, stems, roots, fruits or flowers of a plant. The term "plant" is to be understood as meaning all plants and their parts. Plants are understood here to mean all plants and all organs and parts thereof. The term "parts" is to be understood as meaning individual organs, as well as groups or collections of organs, of a plant. Preferably, the term "parts" is to be understood as meaning leaves, stems, roots, fruits or flowers of a plant. It is specifically preferred to treat plants of the crop plants mentioned above, respectively, with the compounds of the formula I according to the application. Plant cultivars are to be understood as meaning plants which have new properties ("traits") and have been obtained by conventional methods of breeding and selection. These plants can be varieties which have been obtained by means of traditional methods of breeding (varieties having been obtained by hybridization and selection) or by means of the methods of molecular biology (varieties having been obtained by genetic engineering).

[0150] Transgenic plants, seed treatment and inteeration events

[0151] Preferred transgenic plants or plant cultivars (those obtained by genetic engineering) to be treated according to the invention include all plants which, by genetic modification, have received genetic material which imparts particularly advantageous useful properties to these plants. Examples of such properties are: better plant growth, increased tolerance to high or low temperatures, increased 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 storage life and / or processability of the harvested product. Other and particularly emphasized examples of such properties are the increased resistance of plants to animal and microbial pests, for example against insects, arachnids, nematodes, mites, slugs and snails, for example due to toxins formed in the plants, in particular those formed in plants by genetic material from Bacillus thuringiensis (for example by genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and combinations thereof); and the increased resistance of plants to phytopathogenic fungi, bacteria and / or viruses, which is caused, for example, by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and corresponding expressed proteins and toxins; and the increased tolerance of plants to specific active insecticidal ingredients, for example imidazolinones, sulfonylureas, glyphosate or glufosinate (for example the "PAT" gene). The genes that confer the desired properties can be present in combination with one another in transgenic plants. Examples of transgenic plants include important crop plants, such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peas and other types of vegetables, cotton, tobacco, rapeseed, and fruit plants (including the following fruits: apples, pears, citrus fruits and grapes), with particular emphasis on corn, soybeans, wheat, rice, potatoes, cotton, sugar cane, tobacco and rapeseed. Properties that are particularly emphasized are enhanced resistance of the plants to insects, arachnids, nematodes, slugs and snails.

[0152] Crop protection – types of treatments

[0153] 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.

[0154] 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.

[0155] 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.

[0156] Seed treatment

[0157] The control of animal pests by treating the seed of plants has long been known and is the subject of constant improvements. Seed treatment, however, involves a series of problems which cannot always be solved in a satisfactory manner. There is therefore a need to develop methods for protecting seeds and germinating plants which do not require or at least significantly reduce the additional application of pesticides during storage, after sowing or after the emergence of the plants. There is also a need to optimize the amount of active ingredient used in order to provide the seed and the germinating plant with the best possible protection against attack by animal pests, without the active ingredient used impairing the plant itself. 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 seed and the germinating plant with the least possible use of crop protection products.

[0158] 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.

[0159] 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.

[0160] 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.

[0161] 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.

[0162] 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.

[0163] 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.

[0164] It is likewise considered advantageous that the compounds of formula I can also be used, inter alia, for transgenic seed.

[0165] 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.

[0166] 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.

[0167] 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.

[0168] 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.

[0169] 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.

[0170] 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.

[0171] 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.

[0172] 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.

[0173] 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.

[0174] 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.

[0175] 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.

[0176] 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.

[0177] 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.

[0178] 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.

[0179] Useful binders which can be present in the seed dressing preparations used according to the application are all customary binders which can be used in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

[0180] Gibberellins which can be present in the seed dressing preparations used according to the application are preferably gibberellin A1, A3 (= gibberellic acid), A4 and A7, particularly preferred use being made of gibberellic acid.

[0181] The seed dressing preparations 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 preparations obtainable therefrom by dilution with water can be used to coat the seeds of cereals (such as wheat, barley, rye, oats and triticale), and also the seeds of maize, rice, oilseed rape, peas, beans, cotton, sunflower, soybean and sugar beet, or a large number of different vegetable seeds. The seed dressing preparations used according to the application or their dilution forms used can also be used to dress the seeds of transgenic plants.

[0182] For the treatment of the seed with the seed dressing preparations used according to the application or the use forms prepared therefrom, all mixing apparatuses which are customary for seed dressing are available. More particularly, the process for seed dressing is as follows: the seeds are placed in batches or continuously in a mixer; the particular required amount of seed dressing preparation, either as such or after prior dilution with water, is added; and mixing is carried out until the preparation is uniformly distributed over the seeds. If appropriate, a drying operation can be carried out subsequently.

[0183] The application rates of the seed dressing preparations used according to the application can vary within a relatively wide range. They depend on the particular content of compounds of the formula I in the preparation and on the seeds. The application rates of 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.

[0184] For animal health

[0185] In the field of animal health, i.e. veterinary medicine, the active ingredients of the present application are used against animal parasites, especially ectoparasites or, in other embodiments, endoparasites. The term "endoparasites" includes, inter alia, helminths, such as tapeworms, roundworms or flukes; and protozoa, such as coccidia. Ectoparasites are generally and preferably arthropods, especially insects, such as biting and sucking flies, parasitic fly larvae, lice, hair lice, bird lice, fleas and the like; or mites, such as hard ticks or soft ticks; or mites, such as Demodex mites, autumn mites and bird mites and the like; and aquatic ectoparasites, such as copepods.

[0186] 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.

[0187] 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.

[0188] 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.

[0189] In a preferred embodiment, the compounds of formula I are administered to mammals.

[0190] In another preferred embodiment, the compounds of formula I are administered to avians, i.e. caged birds and in particular poultry.

[0191] The use of the compounds of formula I to control animal parasites is intended to reduce or prevent the cases of disease, death and performance reduction (in the case of meat, milk, wool, rawhide, eggs, honey, etc.) so that animal keeping can be more economical and simple and better keeping of the animals in good condition is achieved.

[0192] 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.

[0193] 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.

[0194] 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, especially 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 sprays such as pump sprays and atomised sprays.

[0195] 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.

[0196] In the case of use in the field of animal health, in order to broaden the spectrum of activity, 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.

[0197] Vector control

[0198] The compounds of the formula I are also useful in vector control. In the context of the present application, a vector is an arthropod, especially 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 after injection (for example malaria parasites of mosquitoes).

[0199] 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.

[0200] 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.

[0201] If the compounds of the formula I are resistant to destruction, then vector control is also possible.

[0202] The compounds of the formula I are suitable for the protection of materials, especially natural materials, from the action of insects, for example from the attack or damage by insects from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.

[0203] Protection of industrial materials

[0204] The compounds of the formula I are suitable for protecting industrial materials from the attack or damage by insects, for example from the attack or damage by insects from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.

[0205] In the present context, industrial materials are to be understood as meaning inanimate materials, for example, preferably plastics, adhesives, sizes, paper and paperboard, leather, wood and processed wood products and coating compositions. Particularly preferred is the use of the application for the protection of wood.

[0206] 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.

[0207] 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.

[0208] Surprisingly, it has also been found that the compounds of the formula I can be used for the protection of objects in contact with salt water or slightly brackish water from fouling, especially ship hulls, screens, nets, buildings, mooring equipment and signalling systems. It is likewise possible for the compounds of the formula I to be used as antifouling agents, either alone or in combination with other active ingredients.

[0209] Control of animal pests in the hygiene sector

[0210] 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.

[0211] 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.

[0212] 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

[0213] 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.

[0214] 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 the following Table 1. The specific compound structure and the corresponding compound information are shown in Table 1. The compounds in Table 1 are only for better illustration of the present application, but do not limit the present application, and for those skilled in the art, this should not be understood as the scope of the above-mentioned subject matter of the present application is limited to the following compounds.

[0215] Table 1 Compound structure and its 1 H NMR

[0216]

[0217] Table A and Table B are constructed as Table 1 above except that the generic formula I is replaced by the generic formula I' having a chiral center wherein in Table A, the entries under the column heading "No." recite in order 1 (S) - 187 (S). For example, 1 (S) corresponds to compound 1 in Table 1 having the chiral sulfur in the * position of the generic formula in the S configuration. In Table B, the entries under the column heading "No." recite in order 1 (R) - 187 (R). For example, 1 (R) corresponds to compound 1 in Table 1 having the chiral sulfur in the * position of the generic formula in the R configuration.

[0218] Several methods for preparing the compounds of the present application are illustrated in the following Schemes and Examples. The starting materials are commercially available or can be prepared by known methods in the literature or as illustrated. As will be apparent to those of ordinary skill in the art, other synthetic routes can be used to synthesize the compounds of the present application. Although specific starting materials and conditions are given in the following schemes, other starting materials and conditions can readily be used by those of ordinary skill in the art. The synthesis of the compounds of the present application can be further modified using conventional chemistry methods known to those of ordinary skill in the art. For example, appropriate groups can be protected during the course of the reaction, and the like.

[0219] The following method examples are provided to further illustrate the preparation of the compounds of the present application and are not intended to limit the scope of the application. The reagents used in the synthesis of the compounds shown in the following tables are either commercially available or can be readily prepared by one of ordinary skill in the art.

[0220] The following examples illustrate the preparation of representative compounds. The synthesis of other compounds is analogous and is not described in detail.

[0221] 1. Synthesis of Compound 1

[0222] (1) Compound 1-1 (0.6 g, 2.19 mmol, 1 eq) was dissolved in 20 mL of 1,4-dioxane, and bis(pinacolato)diboron (0.67 g, 2.63 mmol, 1.2 eq), potassium acetate (0.43 g, 4.38 mmol, 2 eq), and a catalytic amount of 1,1'-bis(diphenylphosphino)ferrocene palladium(II) dichloride dichloromethane complex were added successively. The reaction was carried out at 100 °C under a nitrogen atmosphere for 12 h, and the reaction was monitored until the starting material disappeared. The reaction solution was cooled to room temperature, and 1-2 (0.42 g, 2.85 mmol, 1.3 eq), cesium fluoride (0.66 g, 4.38 mmol, 2 eq), H2O (4 mL), and a catalytic amount of 1,1'-bis(diphenylphosphino)ferrocene palladium(II) dichloride dichloromethane complex were added successively. The reaction was carried out at 100 °C for 12 h, and the reaction was monitored until the starting material disappeared. The reaction solution was filtered and concentrated, and the residue was purified by column chromatography to give white solid 1-3 (0.42 g, yield 62.3%).

[0223] (2) Compound 1-3 (0.42 g, 1.36 mmol, 1 eq) was dissolved in 20 mL of DCM, and m-CPBA (0.71 g, 4.08 mmol, 3 eq) was added under ice bath. The reaction was carried out at room temperature for 6 h, and the reaction was monitored until the starting material disappeared. The reaction solution was diluted with dichloromethane, and the organic phase was washed with saturated aqueous sodium bicarbonate solution and saturated brine. The solution was dried, filtered, and concentrated, and the residue was separated by column chromatography to give white solid 1-4 (0.33 g, yield 71.2%).

[0224] (3) Compound 1-4 (0.33 g, 0.96 mmol, 1 eq) was dissolved in a mixture of 10 mL of THF and 3 mL of water, and sodium hydroxide (0.115 g, 2.88 mmol, 3 eq) was added. The reaction was carried out at room temperature for 3 h, and the reaction was monitored until the starting material disappeared. The reaction solution was acidified, and the product was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried, filtered, and concentrated to give yellow oil 1-5 (0.29 g).

[0225] (4) Compound 1-5 (0.29 g, 0.89 mmol, 1 eq) was dissolved in 20 mL of DCM, and compound 1-6 (0.3 g, 1.34 mmol, 1.5 eq), triethylamine (0.18 g, 1.78 mmol, 2 eq) and Py-BOP (0.69 g, 1.34 mmol, 1.5 eq) were added successively. The reaction was allowed to proceed at room temperature for 2 h, and the reaction was monitored until the starting material disappeared. The reaction solution was diluted with dichloromethane, and the organic phase was washed with saturated brine, dried, filtered and concentrated. The residue was separated by column chromatography to obtain compound 1-7 (0.22 g, yield 46.5%) as a yellow solid.

[0226] (5) Compound 1-7 (0.22 g, 0.41 mmol, 1 eq) was dissolved in 20 mL of toluene, and p-toluenesulfonic acid (0.014 g, 0.08 mmol, 0.2 eq) was added. The reaction was allowed to proceed at 100°C for 12 h, and the reaction was monitored until the starting material disappeared. The reaction solution was concentrated, and the residue was diluted with water, extracted with ethyl acetate, washed with saturated brine, dried, filtered and concentrated. The residue was separated by column chromatography to obtain compound 1 (0.052 g, yield 24.5%) as a white solid.

[0227] 2. Synthesis of compound 3

[0228] (1) 3-1 (0.9 g, 1.8 mmol) was dissolved in 20 mL of 1,4-dioxane, and 3-2 (0.68 g, 2.7 mmol) and potassium acetate (0.35 g, 3.6 mmol) were added successively. After nitrogen substitution, a catalytic amount of 1,1'-bis(diphenylphosphino)ferrocene palladium(II) dichloromethane complex was added, and the temperature was slowly increased to 100°C. The reaction was allowed to proceed for 12 h, and the reaction was monitored until the starting material disappeared. The reaction solution was concentrated, and the residue was diluted with water, extracted with ethyl acetate three times, and washed with saturated brine three times. After drying over anhydrous sodium sulfate, the sample was stirred and passed through a column, and the fraction was spin-dried to obtain 3-3 (0.6 g, yield 60%, white solid).

[0229] (2) 3-3 (0.6 g, 1.1 mmol) was dissolved in 20 mL of 1,4-dioxane, and 3-4 (0.16 g, 1.1 mmol), cesium fluoride (0.33 g, 2.2 mmol) and 4 mL of H2O were added successively. After nitrogen substitution, a catalytic amount of 1,1'-bis(diphenylphosphino)ferrocene palladium(II) dichloromethane complex was added, and the temperature was slowly increased to 100°C. The reaction was allowed to proceed for 12 h, and the reaction was monitored until the starting material disappeared. The reaction solution was concentrated, and the residue was diluted with water, extracted with ethyl acetate three times, and washed with saturated brine three times. After drying over anhydrous sodium sulfate, the sample was stirred and passed through a column, and the fraction was spin-dried to obtain compound 3 (0.42 g, yield 75%, white solid).

[0230] 3. Synthesis of compound 25

[0231] Dissolve 25-1 (100 mg, 0.47 mmol) in 10 ml dioxane, add 3-3 (377 mg, 0.71 mmol) and (268 mg, 1.41 mmol), N2 replace, add tetrakis(triphenylphosphine)palladium (54 mg, 0.047 mmol), microwave 130 °C, react 45 min, monitor the reaction until the starting material disappears. The reaction solution is directly added to silica gel sample, normal phase separation, the organic phase is dried to obtain compound 25 (30 mg, yield 11.3%, white solid).

[0232] 4. Synthesis of compound 106

[0233] Dissolve 3-3 (300 mg, 0.566 mmol, 1 eq) and 106-1 (139.39 mg, 0.622 mmol, 1.1 eq) in 20 ml dioxane and 2 ml water, then add cesium fluoride (257.78 mg, 1.70 mmol, 3 eq). The system is protected by nitrogen, and a catalytic amount of catalyst Pd(dppf)Cl2·DCM is added, and then protected by nitrogen. React at 100 degrees Celsius overnight. Monitor the reaction until the starting material disappears, and end the reaction. Concentrate the reaction solution, and purify by normal phase to obtain compound 106 (200 mg, yield 64.58%, white solid).

[0234] 5. Synthesis of compound 113

[0235] (1) Dissolve 113-1 (3.00 g, 10.57 mmol, 1 eq) and 113-2 (2.53 g, 10.57 mmol, 1 eq) in 80 ml dioxane and 8 ml water, then add cesium fluoride (4.82 g, 31.70 mmol, 3 eq). The system is protected by nitrogen, and a catalytic amount of catalyst Pd(dppf)Cl2·DCM is added, and then protected by nitrogen. React at 100 degrees Celsius overnight. Monitor the reaction until the starting material disappears, and end the reaction. Concentrate the reaction solution, and purify by normal phase to obtain compound 113-3 (854 mg, yield 29.98%, white solid).

[0236] (2) Compound 113-3 (150.00 mg, 0.556 mmol, 1 eq) and compound 3-3 (295.15 mg, 0.556 mmol, 1 eq) were dissolved in 20 ml of dioxane and 2 ml of water, then cesium fluoride (253.62 mg, 1.67 mmol, 3 eq) was added. The system was protected by nitrogen, and a catalytic amount of catalyst Pd(dppf)Cl2.DCM was added, and then protected by nitrogen. The reaction was carried out at 100 degrees Celsius overnight. The reaction was monitored until the starting material disappeared, and the reaction was stopped. The reaction solution was concentrated, and compound 113 (90 mg, yield 27.27%, white solid) was obtained by normal phase purification.

[0237] Biological activity evaluation (insecticidal activity test)

[0238] After dilution with acetone, gradient concentrations were prepared; 3-4 leaflets of host plant leaves (young corn leaves) without pesticide and without insect-resistant genes were picked, cut into 3-4 cm long leaves, then placed in a 9 cm outer diameter plastic box, 10 heads of suitable age test insects treated by starvation for 2 h were connected, a spray tower was used for pesticide application, repeated 3 times, with the highest dose containing acetone as a control, after the pesticide application was completed, the box cover was tightly covered, and placed in a treatment room (temperature 25°C, humidity 60%), after 48 h, the number of dead insects was investigated, and the mortality rate was calculated. Mortality rate = (number of dead insects / number of test insects) x 100%

[0239] Table 2 insecticidal activity test results

[0240] Note: N represents no data; control compound A: Control compound B: Control compound C:

[0241] 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, heliothis armigera, beet armyworm, cotton bollworm, spodoptera exigua, armyworm, etc.), Homoptera (e.g. cotton aphid, radish aphid, pea aphid, peanut aphid, green plant bug, etc.), Acarina (e.g. two-spotted spider mite, acaruspis turkestani, etc.), Diptera (e.g. onion thrips, tobacco thrips, etc.), Coleoptera (e.g. yellow striped leaf beetle, small ape leaf beetle, etc.), and Thysanoptera (e.g. palm thrips, onion thrips, tobacco thrips, etc.), as well as Blattidae (e.g. white ant, cockroach, etc.), Muscidae (e.g. fly, mosquito, etc.) and other health pests. Not only have the characteristics of broad-spectrum, high efficiency, strong systemicity, etc., but also can effectively control resistant pests, and have certain commercial value.

Claims

1. A substituted benzisoxazole compound, as shown in the general formula I: in, Z1, Z2, Z3, Z4, and Z5 independently represent N or CR; R independently represents hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, -SF5, -OR 10 、S(O) m R 10 、-N(R 10 )2、-(CO)R 10 、-(CO)OR 10 , cycloalkyl, aryl or heterocyclic; wherein alkyl, alkenyl or alkynyl is optionally selected from halogen, trialkylsilyl, -OR 10 、-S(O) m R 10 , cycloalkyl, heterocyclic or aryl; X represents an alkyl group, a haloalkyl group, an alkenyl group, a haloalkenyl group, an alkynyl group, a haloalkynyl group, -N(R 10 )2, cycloalkyl, cycloalkylalkyl, aryl, heterocyclyl, arylalkyl or heterocyclylalkyl; Y represents an alkyl group; R 10 Each independently represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, aryl or arylalkyl; m represents 0, 1, or 2; The aforementioned "cycloalkyl", "heterocyclyl" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, -OR 11 、-SR 11 、-(CO)R 11 、-(CO)OR 11 、-(CO)N(R 11 )2、-(CS)N(R 11 )2、-(SO)R 11 or -(SO2)R 11 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH-; or a saturated carbon atom on the ring is connected to both ends of unsubstituted or halogen-substituted -OCH2CH2O- to form a ring structure; R 11 Each independently represents hydrogen, alkyl, haloalkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

2. A substituted benzisoxazole compound according to claim 1, characterized in that: R independently represents hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, -SF5, -OR 10 、-S(O) m R 10 、-N(R 10 )2、-(CO)R 10 、-(CO)OR 10 , C3-C8 cycloalkyl, aryl or heterocyclic group; wherein, C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally selected from halogen, tri-C1-C8 alkylsilyl, -OR 10 、-S(O) m R 10 , C3-C8 cycloalkyl, heterocyclic group or aryl group; X represents C1-C8 alkyl, halogenated C1-C8 alkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, -N(R 10 )2, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, aryl, heterocyclyl, arylC1-C8 alkyl or heterocyclylC1-C8 alkyl; Y represents a C1-C8 alkyl group; R 10 Each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl or arylC1-C8 alkyl; The aforementioned "C3-C8 cycloalkyl", "heterocyclyl" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, -OR 11 、-SR 11 、-(CO)R 11 、-(CO)OR 11 、-(CO)N(R 11 )2、-(CS)N(R 11 )2、-(SO)R 11 or -(SO2)R 11 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH-; or a saturated carbon atom on the ring is connected to both ends of unsubstituted or halogen-substituted -OCH2CH2O- to form a ring structure; R 11 Each independently represents hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy.

3. A substituted benzisoxazole compound according to claim 1 or 2, characterized in that: R independently represents hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyano, nitro, -SF5, -OR 10 、-S(O) m R 10 、-N(R 10 )2、-(CO)R 10 、-(CO)OR 10 , C3-C6 cycloalkyl, aryl or heterocyclic group; wherein, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally selected from halogen, tri-C1-C6 alkylsilyl, -OR 10 、-S(O) m R 10 , C3-C6 cycloalkyl, heterocyclic group or aryl group; X represents C1-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, -N(R 10 )2, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, aryl, heterocyclyl, arylC1-C6 alkyl or heterocyclylC1-C6 alkyl; Y represents a C1-C6 alkyl group; R 10 Each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, aryl or arylC1-C6 alkyl; The aforementioned "C3-C6 cycloalkyl", "heterocyclyl" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, -OR 11 、-SR 11 、-(CO)R 11 、-(CO)OR 11 、-(CO)N(R 11 )2、-(CS)N(R 11 )2、-(SO)R 11 or -(SO2)R 11 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH-; or a saturated carbon atom on the ring is connected to both ends of unsubstituted or halogen-substituted -OCH2CH2O- to form a ring structure; R 11 Each independently represents hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, phenyl or phenyl substituted by 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; Preferably, the compound is selected from any one of Table 1, Table A or Table B.

4. A substituted benzisoxazole compound according to the general formula I': in, The carbon atom at position * is a chiral center, and the substituents Z1, Z2, Z3, Z4, Z5, X and Y are defined as described in any one of claims 1 to 3; Based on the content of stereoisomers with R and S configurations at position *, it has a stereochemical purity of 60-100% (S), preferably 70-100%, more preferably 80-100%, further preferably 90-100%, and even more preferably 95-100%; or based on the content of stereoisomers with R and S configurations at position *, it has a stereochemical purity of 60-100% (R), preferably 70-100%, more preferably 80-100%, further preferably 90-100%, and even more preferably 95-100%.

5. A method for preparing a substituted benzisoxazole compound according to any one of claims 1 to 4, characterized in that: The following steps are involved: (1) The compound represented by the general formula II is prepared under acidic conditions to obtain the compound represented by the general formula I, and the reaction equation is as follows: Or (2) the compound represented by the general formula III is reacted with the compound represented by the general formula IV to obtain the compound represented by the general formula I, and the reaction equation is as follows: Or (3) the compound represented by general formula V reacts with the compound represented by general formula VI to obtain the compound represented by general formula I, wherein the reaction equation is as follows: Wherein, among Q1 and Q2, either one is halogen (preferably chlorine), and the other is In Q3 and Q4, either one is SR 21 , and the other is R 21 is a C1-C6 alkyl group or a phenyl group; Z1, Z2, Z3, Z4, Z5, X and Y are as defined in any one of claims 1 to 4; Preferably, the reaction (1) is carried out in the presence of an acid and a solvent; more preferably, the acid is selected from at least one of an inorganic acid or an organic acid; and / or the solvent is selected from at least one of aromatic hydrocarbons, DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate; Preferably, the reaction (2) is carried out in the presence of a base, a catalyst and a solvent; more 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(OAc)2, PdCl2 or 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloromethane complex; and / or the solvent is an organic solvent / water, and the organic solvent is selected from at least one of aromatic hydrocarbons, DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate; Preferably, the reaction (3) is carried out in the presence of cuprous thiophene-2-carboxylate, a catalyst and a solvent; more preferably, the catalyst is selected from at least one of Pd(dppf)Cl2, Pd(OAc)2, PdCl2, or Pd(PPh3)4 or 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloromethane complex; and / or the solvent is selected from at least one of aromatic hydrocarbons (such as benzene, chlorobenzene or toluene), DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate.

6. The preparation method according to claim 5, characterized in that The compound represented by general formula II is prepared by reacting the compound represented by general formula VII with the compound represented by general formula VIII, and the reaction equation is as follows: Wherein, M is OH or halogen; Preferably, the reaction is carried out in the presence of a solvent; more preferably, a condensing agent and / or a base is added during the reaction; further preferably, the base is selected from at least one of an inorganic base or an organic base; the condensing agent is selected from at least one of Py-BOP, Py-AOP, EDCI, HOBT, DCC, HBTU or HATU; and / or the solvent is selected from at least one of aromatic hydrocarbons, DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate.

7. An insecticide composition, characterized in that The invention comprises an insecticidal effective amount of at least one of the substituted benzisoxazole compounds according to any one of claims 1 to 4; preferably, further comprises a formulation adjuvant; more preferably, further comprises other active ingredients.

8. A method for controlling pests, characterized in that: The method comprises contacting the pest or its environment with a biologically effective amount of the substituted benzisoxazole compound according to any one of claims 1 to 4 or the composition according to claim 7.

9. Use of the substituted benzisoxazole compound according to any one of claims 1 to 4 or the composition according to claim 7 in controlling pests.

10. An intermediate, as shown in formula II of claim 5.

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