Pyrazole-substituted aryl sulfide compound and application thereof

Abstract

The invention belongs to the technical field of pesticides, and particularly relates to a pyrazole-substituted aryl sulfide compound and application thereof. The general formula of the compound is shown as I: # imgabs0 #, wherein X is halogen; y is hydrogen, halogen, nitro, cyano or the like; z is alkyl, alkenyl, alkynyl, cycloalkyl or the like; r1 is hydrogen, an amino group, an alkyl group, an alkenyl group, an alkynyl group, a haloalkyl group or the like; r2 and R3 are each independently hydrogen, halogen, alkyl, alkenyl, alkynyl, or the like; the compound has excellent acaricidal activity.

Description

Technical Field

[0001] The present invention belongs to the technical field of pesticides, and particularly relates to a pyrazole-substituted aryl sulfide compound and its application. Background Art

[0002] In crop production in the fields of agriculture and horticulture, damage caused by pests remains serious, and due to the emergence of pests resistant to existing agents, etc., there is a need to develop novel agricultural and horticultural insecticides and acaricides. Due to the increase in the number of elderly agricultural workers, various labor-saving application methods are required, and there is also a need to create agricultural and horticultural insecticides and acaricides with properties suitable for such application methods. Summary of the Invention

[0003] To solve the above problems existing in the prior art, the present invention provides a pyrazole-substituted aryl sulfide compound, and the compound has excellent acaricidal activity.

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

[0005] A pyrazole-substituted aryl sulfide compound, the general formula of which is shown as I:

[0006]

[0007] Wherein, X is a halogen;

[0008] Y is hydrogen, halogen, nitro, cyano, hydroxyl, mercapto, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, -OR 11 or -S(O) n R 11 ;

[0009] Z is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclic group, wherein the "alkyl", "alkenyl" or "alkynyl" is optionally substituted by at least one group selected from halogen, cycloalkyl, cycloalkenyl, aryl, heterocyclic group, hydroxyl, mercapto, -OR 11 or -S(O) n R 11 ;

[0010] R 1 is hydrogen, amino, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, heterocyclic group, aryl, heterocyclic group alkyl or arylalkyl;

[0011] R 2 、R 3 are each independently hydrogen, halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl or -OR 11 ;

[0012] R 11 is an alkyl group, alkenyl group, alkynyl group, haloalkyl group, haloalkenyl group, haloalkynyl group, cycloalkyl group, cycloalkenyl group, aryl group or heterocyclic group;

[0013] The foregoing "cycloalkyl group", "cycloalkenyl group", "heterocyclic group" or "aryl group" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR 10 、-SR 10 、-(CO)OR 10 、-(SO 2 )R 10 、-N(R 10 ) 2 or -O-alkylene-(CO)OR 10 and is substituted by at least one group among them, or two adjacent carbon atoms on the ring and unsubstituted or halogen-substituted -OCH 2 CH 2 - or -OCH 2 O- form a fused ring;

[0014] R 10 are each independently 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;

[0015] n is 0, 1 or 2.

[0016] In a specific embodiment, Y is hydrogen, halogen, nitro, cyano, hydroxy, mercapto, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, -OR 11 or -S(O) n R 11 ;

[0017] Z is C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl or heterocyclic group, wherein the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally selected from halogen, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, heterocyclic group, hydroxy, mercapto, -OR 11 or -S(O) n R 11 and is substituted by at least one group among them;

[0018] R 1is hydrogen, amino, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, heterocyclic group, aryl, heterocyclic group-C1-C8 alkyl or aryl-C1-C8 alkyl;

[0019] R 2 and R 3 each independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl or -OR 11 ;

[0020] R 11 is C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl or heterocyclic group;

[0021] The foregoing "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl", "heterocyclic group" or "aryl" is optionally substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO 2 )R 10 -N(R 10 ) 2 or -O-(C1-C8 alkylene)-(CO)OR 10 , or two adjacent carbon atoms on the ring and unsubstituted or halogen-substituted -OCH 2 CH 2 - or -OCH 2 O- form a fused ring;

[0022] R 10 each independently is hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, phenyl, or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halo-C1-C8 alkoxy.

[0023] In another specific embodiment, Y is hydrogen, halogen, nitro, cyano, hydroxy, mercapto, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, -OR 11 or -S(O) n R 11 ;

[0024] Z is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl or heterocyclic group, wherein the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is optionally substituted by 1 to 3 groups selected from halogen, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclic group, hydroxy, mercapto, -OR 11 or -S(O) n R 11 ;

[0025] R 1 is hydrogen, amino, 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 cycloalkyl C1-C6 alkyl, heterocyclic group, aryl, heterocyclic group C1-C6 alkyl or aryl C1-C6 alkyl;

[0026] R 2 and R 3 each independently represent hydrogen, halogen, 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 cycloalkyl C1-C6 alkyl or -OR 11 ;

[0027] R 11 is 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 cycloalkenyl, aryl or heterocyclic group;

[0028] The aforementioned "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclic group" or "aryl" is optionally substituted by groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR 10 -SR 10, -(CO)OR 10 , -(SO 2 )R 10 , -N(R 10 ) 2 or -O-(C1-C6 alkylene)-(CO)OR 10 is substituted by 1 to 3 groups selected from the following, or two adjacent carbon atoms on the ring and unsubstituted or halogen-substituted -OCH 2 CH 2 - or -OCH 2 O- form a fused ring;

[0029] R 10 is independently hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, phenyl, or phenyl substituted by 1 to 3 groups 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.

[0030] In the definitions of the compounds represented by the above general formula and all the following structural formulas, the technical terms used, whether used alone or in a compound word, represent the following substituents: alkyl groups having more than two carbon atoms may be straight-chain or branched-chain. For example, in the compound word "-O-alkylene-(CO)OR 10 ", the alkylene may be -CH 2 -, -CH 2 CH 2 -,-CH(CH 3 )-,-C(CH 3 ) 2- etc. The alkyl group is, for example, C1 alkyl - methyl; C2 alkyl - ethyl; C3 alkyl - propyl such as n - propyl or isopropyl; C4 alkyl - butyl such as n - butyl, isobutyl, tert - butyl or 2 - butyl; C5 alkyl - pentyl such as n - pentyl; C6 alkyl - hexyl such as n - hexyl, iso - hexyl and 1,3 - dimethylbutyl. Similarly, the alkenyl group is, for example, vinyl, allyl, 1 - methylprop - 2 - en - 1 - yl, 2 - methylprop - 2 - en - 1 - yl, but - 2 - en - 1 - yl, but - 3 - en - 1 - yl, 1 - methylbut - 3 - en - 1 - yl and 1 - methylbut - 2 - en - 1 - yl. The alkynyl group is, for example, ethynyl, propargyl, but - 2 - yn - 1 - yl, but - 3 - yn - 1 - yl, 1 - methylbut - 3 - yn - 1 - yl. The multiple bond can be at any position of each unsaturated group. The cycloalkyl group is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, the cycloalkenyl group is a monocyclic alkenyl group having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, where the double bond can be at any position. The halogen is fluorine, chlorine, bromine or iodine.

[0031] Unless otherwise specified, the "aryl" as used in the present invention includes, but is not limited to, phenyl, naphthyl, The "heterocyclic group" includes, but is not limited to, saturated or unsaturated non - aromatic cyclic groups

[0032] and also includes, but is not limited to, heteroaryl, i.e., an aromatic cyclic group containing, for example, 3 to 6 ring atoms and also optionally having a benzo - fused ring, and 1 to 4 (e.g., 1, 2, 3 or 4) of the ring atoms being heteroatoms selected from oxygen, nitrogen and sulfur, for example

[0033] If a group is substituted by a group, this should be understood to mean that the group is substituted by one or more identical or different groups selected from the groups mentioned. Additionally, the identical or different substitution characters contained in the identical or different substituents are independently selected and can be the same or different. This also applies to ring systems formed by different atoms and units. At the same time, the scope of the claims will exclude those compounds that are chemically unstable under standard conditions and are known to those skilled in the art.

[0034] In addition, unless otherwise specifically defined, the term "substituted by at least one group" as used in the present invention means substituted by, for example, 1, 2, 3, 4, or 5 groups; for a group without a specific connection position indicated (including a heterocyclic group, an aryl group, etc.), it can be connected at any position, including the position connected to C or N; if it is substituted, the substituent can also be substituted at any position as long as it conforms to the chemical bond connection rule. For example, a heteroaryl group substituted by one methyl group may represent

[0035] The present invention also provides a pyrazole-substituted aryl sulfide compound represented by Formula I':

[0036]

[0037] wherein the sulfur atom is a chiral center, and the substituents R 1 、R 2 、R 3 、X, Y, and Z are defined as described above;

[0038] Based on the content of the stereoisomers with R and S configurations of the sulfur atom, 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%.

[0039] Among them, "stereochemical purity" refers to the percentage of the amount of the stereoisomers described in the total amount of the stereoisomers that generate the chiral center.

[0040] In the present invention, the stereochemical configuration at the position marked with * in formula I is determined as predominantly (R) according to the Cahn-Ingold-Prelog system. However, the subject matter of the present invention also relates to all stereoisomers at 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 illustrated in formula I. It should be understood that the present invention includes pure isomers and mixtures thereof enriched to varying degrees of pure isomers, wherein the asymmetric carbon atom at the position marked with * is in the R-configuration, or in the mixture, the compound or compounds of the same chemical structure have the R-configuration at the position marked with *, or are present in a proportion such that the compound with the R-configuration is predominantly present (at least 60% R-configuration), while the other asymmetric carbon atoms may be present in racemic form or may also be resolved to varying degrees. As long as the stereochemical configuration conditions at the position marked with * are met, the possible stereoisomers defined by specific spatial forms, such as enantiomers, diastereomers, Z- and E-isomers, are all included in formula I and can be obtained from mixtures of stereoisomers by conventional methods, or can also be prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.

[0041] If various functional groups are present, the present invention also includes any keto and enol tautomeric forms and mixtures and salts thereof.

[0042] Stereoisomers can be obtained by optical resolution from mixtures obtained in the preparation. Stereoisomers can also be selectively prepared by using stereoselective reactions and using optically active starting materials and / or auxiliaries. For optical resolution, conventional methods can generally be utilized (see Textbooks of Stereochemistry), for example, the following methods for resolving mixtures into diastereomers, such as physical methods, such as crystallization, chromatography, especially column chromatography and high-pressure liquid chromatography, distillation methods carried out under reduced pressure as required, extraction methods and other methods, and generally chromatographic separation on a chiral solid phase can be used to separate residual mixtures of enantiomers. Suitable for preparative amounts or for industrial scale are methods such as crystallizing diastereomeric salts, which can be obtained from the compound using an optically active acid, and if acidic groups are present, an optically active base can be used as required.

[0043] The present invention also provides a method for preparing a pyrazole-substituted aryl sulfide compound, comprising the following steps:

[0044] (1) When n represents 0, a substitution reaction occurs between compound II and compound III or between compound IV and compound V to obtain compound I-1;

[0045] (2) When n represents 1 or 2, compound I-1 is oxidized to obtain compound I-2 or compound I-3;

[0046] The chemical reaction equation is as follows:

[0047]

[0048] wherein, Hal represents a halogen, preferably Br, and Q represents other substituents R 1 、R 2 、R 3 、X, Y and Z are defined as described above.

[0049] In a specific embodiment, step (1) is carried out in the presence of a solvent.

[0050] In another specific embodiment, a catalyst and / or a base are added in step (1).

[0051] In another specific embodiment, the base in step (1) is selected from at least one of inorganic bases (such as K 2 CO 3 、Na 2 CO 3 、Cs 2 CO 3 、NaHCO 3 、KHCO 3 、KF, CsF, KI, NaI, K 3 PO 4 、K 2 HPO 4 、NaOH, KOH, NaH, KH, etc.) or organic bases (such as pyrazole, triethylamine, DIEA, potassium trimethylsilanolate, AcOK, AcONa, MeONa, EtONa, t-BuONa, etc.).

[0052] In another specific embodiment, the catalyst in step (1) is selected from at least one of Pd(dppf)Cl 2 、Pd(PPh 3 ) 4 、PdCl 2 、Pd(OAc) 2 、Pd(PPh 3 ) 2 Cl 2 、NiCl 2 (dppf) and PdCl 2 (dppf)·CH 2 Cl 2 (CAS No.: 95464-05-4).

[0053] In a specific embodiment, step (2) is carried out in the presence of an oxidant and a solvent.

[0054] In another specific embodiment, the oxidant in step (2) is selected from at least one of m-chloroperbenzoic acid, H 2 O 2 , NaClO or KMnO 4 .

[0055] In another specific embodiment, the solvents in steps (1) and (2) are each independently selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane, tetrahydrofuran, toluene, ethyl acetate or water.

[0056] The present invention also provides an intermediate, which is represented by Compound II, III, IV or V.

[0057] Due to the combination of good plant tolerance, favorable toxicity to warm-blooded animals and good environmental tolerance, the active compounds of the present invention are suitable for protecting plants and plant organs, increasing yields, improving the quality of harvested products and controlling animal pests, especially insects, arachnids, worms, nematodes and mollusks encountered in the fields of agriculture, horticulture, animal husbandry, forestry, parks and leisure facilities, protecting stored products and materials, and hygiene. They can preferably be used as plant protection agents. They are active against normally sensitive and resistant species and all or certain developmental stages. The above pests include:

[0058] Sucking lice (Anoplura) (Phthiraptera), such as Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.

[0059] Arachnida, e.g., Acarus spp., Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Amphitertranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Halotydeus destructor, Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Nuphersa spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.

[0060] Class Bivalva, e.g., Dreissena spp.

[0061] Chilopoda, e.g., Geophilus spp., Scutigera spp.

[0062] Coleoptera, e.g., Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Cassida spp., Cerotoma trifurcata, Ceutorhynchus spp., Chaetocnema spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Ctenicera spp., Curculio spp., Cryptorhynchus lapathi, Cylindrocopturus spp., Dermestes spp., Diabrotica spp., Dichocrocis spp., Diloboderus spp., Epilachna spp., Epitrix spp., Faustinus spp., Gibbium psylloides, Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Lema spp.)、Colorado potato beetle (Leptinotarsa decemlineata), leafminer moths (Leucoptera spp.), rice water weevil (Lissorhoptrus oryzophilus), Lixus spp., Luperodes spp., powderpost beetles (Lyctus spp.), Megascelis spp., Melanotus spp., rape pollen beetle (Meligethes aeneus), Melolontha spp., Migdolus spp., sawyer beetles (Monochamus spp.), Naupactus xanthographus, white spider beetle (Niptus hololeucus), coconut rhinoceros beetle (Oryctes rhinoceros), sawtoothed grain beetle (Oryzaephilus surinamensis), Oryzaphagus oryzae, Otiorrhynchus spp., small green flower chafer (Oxycetonia jucunda), turnip flea beetle (Phaedon cochleariae), leaf-eating chafers (Phyllophaga spp.), flea beetles (Phyllotreta spp.), Japanese beetle (Popillia japonica), Premnotrypes spp., flea beetles (Psylliodes spp.), spider beetles (Ptinus spp.), black ladybird (Rhizobius ventralis), lesser grain borer (Rhizopertha dominica), grain weevils (Sitophilus spp.), Sphenophorus spp., Sternodema spp., Symphyletes spp., Tanymecus spp., yellow mealworm (Tenebrio molitor), flour beetles (Tribolium spp.), hide beetles (Trogoderma spp.), Tychius spp., Xylotrechus spp., Zabrus spp..

[0063] Collembola, e.g., Onychiurus armatus.

[0064] Diplopoda, e.g., Blaniulus guttulatus.

[0065] Diptera, such as Aedes spp., Agromyza spp., Anastrepha spp., Anopheles spp., Asphondylia spp., Bactrocera spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chironomus spp., Chrysomyia spp., Cochliomyia spp., Contarinia spp., Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dasyneura spp., Delia spp., Dermatobia hominis, Drosophila spp., Echinocnemus spp., Fannia spp., Gastrophilus spp., Hydrellia spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia, Phorbia spp., Prodiplosis spp., Psila rosae, Rhagoletis spp., Stomoxys spp., Tabanus spp., Tannia spp., Tetanops spp., Tipula spp.

[0066] Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.

[0067] Helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciolaspp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagiaspp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp.) Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.

[0068] In addition, it can also control protozoa, such as Eimeria.

[0069] Heteroptera, for example, Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Monalonion atratum, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.

[0070] Homoptera, for example, Acyrthosipon spp., Acrogoniaspp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphisspp, Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicorynebrassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilu shalli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Ferrisia spp., Geococcus coffeae, Hieroglyphus spp., Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoidestitanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes spp., Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp..

[0071] Hymenoptera, for example, Athalia spp., Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp..

[0072] Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber.

[0073] Isoptera, for example, Acromyrmex spp., Atta spp., Cornitermes cumulans, Microtermes obesi, Odontotermes spp., Reticulitermes spp..

[0074] Lepidoptera, for example, Acronicta major, Adoxophyes spp., Aedia leucomelas, Agrotis spp., Alabama spp., Amyelois transitella, Anarsia spp. (Anarsia), Anticarsia spp., Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora., Capuareticulana, Carpocapsa pomonella, Carposina niponensis., Cheimatobia brumata, Chilo spp., Choristoneuraspp., Clysia ambiguella, Cnaphalocerus spp., Cnephasiaspp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydiaspp., Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias insulana, Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia spp.)、Greater Wax Moth (Galleria mellonella), Gracillaria spp., Grapholitha spp., Hedylepta spp., Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Apple Ermine Moth (Hyponomeuta padella), Persimmon Fruit Moth (Kakivoria flavofasciata), Laphygma spp., Oriental Fruit Moth (Laspeyresia molesta), Eggplant Fruit Borer (Leucinodes orbonalis), Leucoptera spp, Lithocolletis spp., Apple Green Fruitworm (Lithophane antennata), Lobesia spp., Albicosta Cutworm (Loxagrotis albicosta), Lymantria spp., Lyonetia spp., Fall Webworm (Malacosoma neustria), Legume Pod Borer (Maruca testulalis), Cabbage Moth (Mamestra brassicae), Mocis spp., Oriental Armyworm (Mythimna separata), Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp., Ostrinia spp., Rice Flea Beetle (Oulema oryzae), Pine Beauty Moth (Panolis flammea), Parnara spp., Pectinophora spp., Perileucoptera spp., Potato Tuber Moth (Phthorimaea spp.), Citrus Leafminer (Phyllocnistis citrella), Phyllonorycter spp., Pieris spp., Platynota stultana, Plusia spp., Diamondback Moth (Plutella xylostella), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Scirpophaga spp., Scotiasegetum, Sesamia spp., Sparganothis spp., Spodoptera spp., Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichoplusia spp., Tuta absoluta, Virachola spp..

[0075] Orthoptera, for example, Acheta domesticus, Blatta orientalis, Blattella germanica, Dichroplus spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.

[0076] Siphonaptera, for example, Ceratophyllus spp. and Xenopsylla cheopis.

[0077] Symphyla, for example, Scutigerella spp.

[0078] Thysanoptera, for example, Anaphothrips obscurus, Baliothrips biformis, Drepanothris reuteri, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.

[0079] Thysanura, for example, Lepisma saccharina.

[0080] Plant parasitic nematodes include, for example, Aphelenchoides spp., Bursaphelenchus spp., Ditylenchus spp., Globodera spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Trichodorus spp., Tylenchulus semipenetrans, Xiphinema spp.

[0081] If appropriate, the active compound combinations of the present invention can also be used as herbicides, safeners, growth regulators, or as agents for improving plant characteristics, or as microbicides, for example fungicides, antimycotics, bactericides, virucides (including agents against viroids) or as agents against MLO (mycoplasma-like organisms) and RLO (rickettsia-like organisms) at a certain concentration or application rate. If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds.

[0082] The present invention also relates to formulations comprising at least one active compound of the present invention and use forms prepared from these formulations as crop protection compositions and / or pesticides, such as drenches, drip infusions and spray liquors. The use forms optionally contain other crop protection agents and / or pesticides and / or activity-enhancing auxiliaries such as penetrants, such as vegetable oils (e.g., rapeseed oil, sunflower oil), mineral oils (e.g., paraffin oil), alkyl esters of plant fatty acids (e.g., rapeseed oil methyl ester or soybean oil methyl ester) or alkanol alkoxylates, and / or spreaders such as alkyl siloxanes and / or salts, such as organic or inorganic ammonium or phosphonium salts (e.g., ammonium sulfate or diammonium hydrogen phosphate), and / or retention promoters such as dioctyl sulfosuccinate or hydroxypropyl guar gum polymers, and / or wetting agents such as glycerol and / or fertilizers, such as fertilizers containing ammonium, potassium or phosphorus.

[0083] Conventional formulations include, for example, water-soluble liquids (SL), emulsion concentrates (EC), oil-in-water emulsions (EW), suspensions (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS); the above and other possible formulation types are described, for example, by Crop Life International in Pesticide Specifications, Manual on development and use of FAO, and WHO specifications for pesticides, FAO Plant Production and Protection Papers-173, 2004, ISBN: 9251048576, prepared by the FAO / WHO Joint Meeting on Pesticide Specification. In addition to one or more active compounds of the present invention, the formulations optionally contain other agrochemical active compounds.

[0084] Preferred are formulations or use forms comprising auxiliaries (such as fillers, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or other auxiliaries, such as adjuvants). The adjuvants in the present invention are components that enhance the biological effect of the formulation, while the components themselves do not have a biological effect. Examples of adjuvants are agents that promote retention, spreading, attachment to the leaf surface or penetration.

[0085] These formulations are prepared in a known manner, for example by mixing the active compound with auxiliaries such as fillers, solvents and / or solid carriers and / or other auxiliaries such as surfactants. These formulations are prepared in suitable devices or are prepared before or during use.

[0086] Substances used as auxiliaries are suitable for imparting certain properties, such as certain physical, technological and / or biological properties, to active compound formulations and / or use forms prepared therefrom (e.g., ready-to-use crop protection compositions, such as spray liquors or seed dressings).

[0087] Suitable fillers are, for example, water, polar and non-polar organic chemical liquids, such as aromatic and non-aromatic hydrocarbons (e.g., paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified if appropriate), ketones (e.g., acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides, lactams (e.g., N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (e.g., dimethyl sulfoxide).

[0088] If the filler used is water, organic solvents can also be used as cosolvents, for example. Suitable liquid solvents mainly include: aromatic compounds, such as xylene, toluene or alkylnaphthalene; chlorinated aromatic compounds and chlorinated aliphatic hydrocarbons, such as chlorobenzene, vinyl chloride or dichloromethane; aliphatic hydrocarbons, such as cyclohexane or paraffins, such as petroleum fractions, mineral oils and vegetable oils; alcohols, such as butanol or ethylene glycol, and their ethers and esters; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide; and water.

[0089] In principle, all suitable solvents can be used. Examples of suitable solvents are aromatic hydrocarbons such as xylene, toluene or alkylnaphthalene, chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons, such as chlorobenzene, vinyl chloride or dichloromethane; aliphatic hydrocarbons, such as cyclohexane, paraffins, petroleum fractions, mineral oils and vegetable oils; alcohols, such as methanol, ethanol, isopropanol, butanol or ethylene glycol, and their ethers and esters; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strongly polar solvents, such as dimethyl sulfoxide; and water.

[0090] In principle, all suitable carriers can be used. Useful carriers especially include: for example, ammonium salts and ground natural minerals, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and natural and synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of the said carriers can also be used. Solid carriers suitable for granulates are: for example, ground and classified 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 husk, corn cobs and tobacco stems.

[0091] It is also possible to use liquefied gas fillers or solvents. Particularly suitable fillers or carriers are those which are gaseous at room temperature and atmospheric pressure, such as aerosol propellants, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.

[0092] Examples of emulsifiers and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties, or mixtures of these surfactants include salts of polyacrylates, lignosulfonates, salts of phenolsulfonic or naphthalenesulfonic acids, condensation products of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines or with substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinates, taurine derivatives (such as alkyltaurates), phosphates of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of compounds containing sulfates, sulfonates and phosphates, such as alkylaryl polyethylene glycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, or protein hydrolysates, lignosulfite waste liquors and methylcellulose. The presence of surfactants is advantageous if one of the active compounds and / or one of the inert carriers is insoluble in water and the application takes place in water.

[0093] Other auxiliaries which can be present in the formulations and in the use forms derived therefrom include dyes, such as inorganic pigments, such as iron oxide, titanium oxide and Prussian blue; and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes; and nutrients and micronutrients, such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts and zinc salts.

[0094] Other components can be stabilizers, such as cryostabilizers, preservatives, antioxidants, light stabilizers or other reagents which improve chemical and / or physical stability. Foaming agents or defoaming agents can also be present.

[0095] Thickeners can also be present as other auxiliaries in the formulations and in the use forms prepared from the formulations, such as: carboxymethyl cellulose; and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate; or other natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids. Other possible auxiliaries are mineral oils and vegetable oils.

[0096] Optionally, other auxiliaries can also be present in the formulations and in the use forms derived from the formulations. Examples of such additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic agents, penetrants, retention promoters, stabilizers, chelating agents, complexing agents, wetting agents, spreading agents. In general, the active compounds can be combined with any solid or liquid additives which are commonly used for formulation purposes.

[0097] Useful retention promoters include all those substances which reduce the dynamic surface tension, such as dioctyl sulfosuccinate; or those which increase the viscoelasticity, such as hydroxypropyl guar polymers.

[0098] In the context of the present invention, useful penetrants are all those substances which are customarily used to increase the ability of agrochemical active compounds to penetrate into plants. In the context of the present invention, penetrants are defined by their ability to penetrate from the (usually aqueous) application liquid and / or spray coating into the plant cuticle and thus to increase the mobility of the active compound in the cuticle. This property can be determined by the method described in the literature (Baur et al., 1997, Pesticide Science 51, 131 - 152). Examples include alkanol alkoxides, such as coconut oil fatty acid ethoxylate (10) or isotridecyl ethoxylate (12); fatty acid esters such as rapeseed oil methyl ester or soybean oil methyl ester; fatty amine alkoxides such as tallow amine ethoxide (15); or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.

[0099] The formulation contains preferably from 0.00000001 to 98% by weight, more preferably from 0.01% to 95% by weight, even more preferably from 0.5% to 90% by weight of the active ingredient, based on the weight of the formulation.

[0100] The active ingredient content of the use form (crop protection composition) prepared from the formulation can vary within a wide range. The active ingredient concentration of the use form can generally be from 0.00000001 to 95% by weight of the active ingredient, preferably from 0.00001 to 1% by weight of the active ingredient, based on the weight of the use form. Application is carried out in a conventional manner adapted to the use form.

[0101] The active compounds of the invention can be used per se or in the form of their preparations, which preparations include mixtures with one or more suitable fungicides, bactericides, acaricides, nematicides, insecticides, microbicides, fertilizers, attractants, sterilants, synergists, safeners, chemical pheromones and / or plant growth regulators, for the purpose of, for example, broadening the activity spectrum, prolonging the duration of action, increasing the rate of action, preventing repulsion or preventing the development of resistance. In addition, plant growth can be improved by those combinations, which can improve abiotic stress factor tolerance, for example, increasing tolerance to high or low temperatures, increasing tolerance to drought or to the salt content in water and / or soil. It is also possible to improve the quality of flowering and fruiting, optimize germination performance and root development, simplify harvesting and increase the yield, accelerate ripening, improve the quality and / or nutritional value of the harvested product, extend the storage life of the harvested product and / or improve its processing properties. In general, the active compounds of the invention and the combinations of the co-components produce a synergistic effect, i.e., the efficacy of the mixture is greater than the efficacy of the individual components. The combinations can generally be used in the form of a premix, a tank mix or a made-to-order mix or can also be used in seed applications.

[0102] Particularly advantageous co-components are, for example, those listed below.

[0103] Insecticides / acaricides / nematicides:

[0104] The active compounds indicated here by their common names are known and described, for example, in The Pesticide Manual (14th Edition, British Crop Protection Council 2006) or can be looked up on the Internet (for example, http: / / www.alanwood.net / pesticide).

[0105] (1) Acetylcholinesterase (AChE) inhibitors, such as carbamates, for example, 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, xylylcarb;

[0106] or organophosphates, such as acephate, 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, O-(methoxyaminothiophosphoryl) salicylate, isoxathion, 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, sulphotep, tebupirimfos,Temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon, vamidothion.

[0107] (2) GABA - gated chloride channel antagonists, such as cyclodiene organochlorines, such as chlordane and endosulfan;

[0108] Or phenylpyrazoles (fiprols), such as ethiprole, fipronil.

[0109] (3) Sodium channel modulators / voltage-dependent sodium channel blockers, for example, pyrethroids, for example,Acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, resmethrin, cycloprothrin, cyfluthrin, cyfluthrin, β-cyfluthrin, cyhalothrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, Halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin, pyrethrine (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) isomer], tralomethrin, transfluthrin;

[0110] or DDT; or methoxychlor.

[0111] (4) Nicotinic acetylcholine receptor (nAChR) agonists, such as neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; or nicotine.

[0112] (5) Allosteric activators of nicotinic acetylcholine receptor (nAChR), such as spinosyns, such as spinetoram and spinosad.

[0113] (6) Chloride channel activators, such as avermectins / milbemycins, such as abamectin, emamectin-benzoate, lepimectin, milbemycin.

[0114] (7) Juvenile hormone mimics, such as juvenile hormone analogs, such as hydroprene, kinoprene, methoprene; or fenoxycarb; or pyriproxifen.

[0115] (8) Active substances with unknown or non-specific mechanisms of action, such as alkyl halides, such as methyl bromide, other alkyl halides; or chloropicrin; or sulfuryl chloride; or borax; or tartar emetic.

[0116] (9) Selective feeding deterrents, such as pymetrozine; or flonicamid.

[0117] (10) Mite growth inhibitors, such as clofentezine, hexythiazox, diflovidazin; or etoxazole.

[0118] (11) Insect gut membrane microbial disruptors, such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, BT crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1.

[0119] (12) Oxidative phosphorylation inhibitors, ATP disruptors, such as diafenthiuron; or organotin acaricides, such as azocyclotin, cyhexatin, fenbutatin-oxide; or propargite; or tetradifon.

[0120] (13) Oxidative phosphorylation uncouplers that act by disrupting the H+ proton gradient, such as chlorfenapyr, DNOC, sulfluramid.

[0121] (14) Nicotinic acetylcholine receptor channel blockers, such as bensultap, cartap hydrochloride, thiocyclam, thiosultap-sodium.

[0122] (15) Chitin biosynthesis inhibitors, type 0, such as bistrifluron, chlofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron.

[0123] (16) Chitin biosynthesis inhibitors, type 1, such as buprofezin.

[0124] (17) Molting disruptors, for dipteran insects, such as cyromazine.

[0125] (18) Ecdysteroid receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide, tebufenozide.

[0126] (19) Octopaminergic agonists, such as amitraz.

[0127] (20) Complex III electron transfer inhibitors, such as hydramethylnon, acequinocyl, or fluacrypyrim.

[0128] (21) Complex I electron transfer inhibitors, such as METI acaricides, such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; or rotenone (Derris).

[0129] (22) Voltage-dependent sodium channel blockers, such as indoxacarb; or metaflumizone.

[0130] (23) Acetyl-CoA carboxylase inhibitors, such as tetramic acids and their derivatives, such as spirodiclofen, spiromesifen, spirotetramat.

[0131] (24) Complex IV electron transfer inhibitors, such as phosphines, such as aluminium phosphide, calcium phosphide, phosphine, zinc phosphide; or cyanides.

[0132] (25) Complex II electron transfer inhibitors, such as cyenopyrafen.

[0133] (28) Ryanodine receptor modulators, such as diamides, such as chlorantraniliprole and flubendiamide.

[0134] Other active ingredients with unknown or undetermined mechanisms of action, such as, amidoflumet, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite, cyantraniliprole (cyazypyr), cyflumetofen, dicofol, diflovidazin, fluensulfone, flufenerim, flufiprole, fluopyram, fufenozide, Imidaclothiz, iprodione, meperfluthrin, pyridalyl, Pyrifluquinazon, tetramethylfluthrin, methyl iodide; and preparations based on Bacillus firmus (in particular strain CNCM I-1582, such as, for example, VOTiVO TM , BioNem), or the following known active compounds:

[0135] 3-Bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (known from WO2005 / 077934), 4-{[(6-bromopyridin-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one (known from WO2007 / 115644), 4-{[(6-fluoropyridin-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one (known from WO2007 / 115644), 4-{[(2-chloro-1,3-thiazol-5-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one (known from WO2007 / 115644), 4-{[(6-chloropyridin-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one (known from WO2007 / 115644), Flupyradifurone, 4-{[(6-chloro-5-fluoropyridin-3-yl)methyl](methyl)amino}furan-2(5H)-one (known from WO2007 / 115643), 4-{[(5,6-dichloropyridin-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one (known from WO2007 / 115646), 4-{[(6-chloro-5-fluoropyridin-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one (known from WO2007 / 115643), 4-{[(6-chloropyridin-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one (known from EP-A-0539588), 4-{[(6-chloropyridin-3-yl)methyl](methyl)amino}furan-2(5H)-one (known from EP-A-0539588), {[1-(6-chloropyridin-3-yl)ethyl](methyl)oxid-λ 4 -sulfanylidene}aminonitrile (known from WO2007 / 149134) and its diastereomer {[(1R)-1-(6-chloropyridin-3-yl)ethyl](methyl)oxid-λ 4 -sulfanylidene}aminonitrile (A) and {[(1S)-1-(6-chloropyridin-3-yl)ethyl](methyl)oxid-λ 4 -sulfanylidene}aminonitrile (B) (known from WO2007 / 149134) and sulfoxaflor and its diastereomer [(R)-methyl(oxid){(1R)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ 4 -sulfanylidene]aminonitrile (A1) and [(S)-methyl(oxid){(1S)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ 4-Thioalkyl] cyanamide (A2), known as diastereoisomer group A (known from WO2010 / 074747, WO2010 / 074751), [(R)-methyl(oxo){(1S)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ 4 -Thioalkyl] cyanamide (B1) and [(S)-methyl(oxo){(1R)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ 4-Thiolan-1-yl]cyanamide (B2), referred to as diastereoisomer group B (known from WO2010 / 074747, WO2010 / 074751), and 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxo-9-azadispiro[4.2.4.2]tetradec-11-en-10-one (known from WO2006 / 089633), 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one (known from WO2008 / 067911), 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO2006 / 043635), [(3S,4aR,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-6,12-dihydroxy-4,12b-dimethyl-11-oxo-9-(pyridin-3-yl)-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-benzo[f]pyrano[4,3-b]benzopyran-4-yl]methyl cyclopropanecarboxylate (known from WO2008 / 066153), 2-cyano-3-(difluoromethoxy)-N,N-dimethylbenzenesulfonamide (known from WO2006 / 056433), 2-cyano-3-(difluoromethoxy)-N-methylbenzenesulfonamide (known from WO2006 / 100288), 2-cyano-3-(difluoromethoxy)-N-ethylbenzenesulfonamide (known from WO2005 / 035486), 4-(difluoromethoxy)-N-ethyl-N-methyl-1,2-benzothiazol-3-amine 1,1-dioxide (known from WO2007 / 057407), N-[1-(2,3-dimethylphenyl)-2-(3,5-dimethylphenyl)ethyl]-4,5-dihydro-1,3-thiazol-2-amine (known from WO2008 / 104503), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4'-piperidine]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO2003 / 106457), 3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-azadispiro[4.5]dec-3-en-2-one (known from WO2009 / 049851), 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-azadispiro[4.5]dec-3-en-4-yl ethyl formate (known from WO2009 / 049851), 4-(but-2-yn-1-yloxy)-6-(3,5-Dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO2004 / 099160), (2,2,3,3,4,4,5,5-octafluoropentyl)(3,3,3-trifluoropropyl)malononitrile (known from WO2005 / 063094), (2,2,3,3,4,4,5,5-octafluoropentyl)(3,3,4,4,4-pentafluorobutyl)malononitrile (known from WO2005 / 063094), 8-[2-(Cyclopropylmethoxy)-4-(trifluoromethyl)phenoxy]-3-[6-(trifluoromethyl)pyridazin-3-yl]-3-azabicyclo[3.2.1]octane (known from WO2007 / 040280), Flometoquin, PF1364 (CAS-Registry Number 1204776-60-2) (known from JP2010 / 018586), 5-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile (known from WO2007 / 075459), 5-[5-(2-Chloropyridin-4-yl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile (known from WO2007 / 075459), 4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}benzamide (known from WO2005 / 085216), 4-{[(6-Chloropyridin-3-yl)methyl](cyclopropyl)amino}-1,3-oxazol-2(5H)-one, 4-{[(6-Chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino}-1,3-oxazol-2(5H)-one, 4-{[(6-Chloropyridin-3-yl)methyl](ethyl)amino}-1,3-oxazol-2(5H)-one, 4-{[(6-Chloropyridin-3-yl)methyl](methyl)amino}-1,3-oxazol-2(5H)-one (all known from WO2010 / 005692), NNI-0711 (known from WO2002 / 096882), 1-Acetyl-N-[4-(1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl)-3-isobutylphenyl]-N-isobutyryl-3,5-Dimethyl-1H-pyrazole-4-carboxamide (known from WO2002 / 096882), methyl 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylate (known from WO2005 / 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 WO2005 / 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 WO2005 / 085216), methyl 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-diethylhydrazinecarboxylate (known from WO2005 / 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 WO2005 / 085216), (5RS,7RS; 5RS,7SR)-1-(6-chloropyridin-3-ylmethyl)-1,2,3,5,6,7-hexahydro-7-methyl-8-nitro-5-propoxyimidazo[1,2-a]pyridine (known from WO2007 / 101369), 2-{6-[2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-yl}pyrimidine (known from WO2010 / 006713), 2-{6-[2-(pyridin-3-yl)-1,{3-Thiazol-5-yl}pyridin-2-yl}pyrimidine (known from WO2010 / 006713), 1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-1H-tetrazol-1-yl]methyl}-1H-pyrazole-5-carboxamide (known from WO2010 / 069502), 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 WO2010 / 069502), N-[2-(tert-butylcarbamoyl)-4-cyano-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)-1H-tetrazol-1-yl]methyl}-1H-pyrazole-5-carboxamide (known from WO2010 / 069502), N-[2-(tert-butylcarbamoyl)-4-cyano-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide (known from WO2010 / 069502), (1E)-N-[(6-chloropyridin-3-yl)methyl]-N'-cyano-N-(2,2-difluoroethyl)ethanimidamide (known from WO2008 / 009360), N-[2-(5-amino-1,3,4-thiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (known from CN102057925), methyl 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-yl]carbonyl}amino)benzoyl]-2-ethyl-1-methylhydrazinecarboxylate (known from WO2011 / 049233).

[0136] Fungicide

[0137] (1) Inhibitors of ergosterol biosynthesis: for example, (1.1) aldimorph (1704-28-5), (1.2) azaconazole (60207-31-0), (1.3) bitertanol (55179-31-2), (1.4) bromuconazole (116255-48-2), (1.5) cyproconazole (113096-99-4), (1.6) diclobutrazole (75736-33-3), (1.7) difenoconazole (119446-68-3), (1.8) diniconazole (83657-24-3), (1.9) diniconazole-M (83657-18-5), (1.10) dodemorph (1593-77-7), (1.11) dodemorph acetate (31717-87-0), (1.12) epoxiconazole (106325-08-0), (1.13) etaconazole (60207-93-4), (1.14) fenarimol (60168-88-9), (1.15) fenbuconazole (114369-43-6), (1.16) fenhexamid (126833-17-8), (1.17) fenpropidin (67306-00-7), (1.18) fenpropimorph (67306-03-0), (1.19) fluquinconazole (136426-54-5), (1.20) flurprimidole (56425-91-3), (1.21) flusilazole (85509-19-9), (1.22) flutriafol (76674-21-0), (1.23) furconazole (112839-33-5), (1.24) furconazole-cis (112839-32-4), (1.25) hexaconazole (79983-71-4), (1.26) imazalil (60534-80-7), (1.(27) Imazalil sulfate (58594-72-2), (1.28) Imibenconazole (86598-92-7), (1.29) Ipconazole (125225-28-7), (1.30) Metconazole (125116-23-6), (1.31) Myclobutanil (88671-89-0), (1.32) Naftifine (65472-88-0), (1.33) Nuarimol (63284-71-9), (1.34) Oxpoconazole (174212-12-5), (1.35) Paclobutrazol (76738-62-0), (1.36) Pefurazoate (101903-30-4), (1.37) Penconazole (66246-88-6), (1.38) Piperalin (3478-94-2), (1.39) Prochloraz (67747-09-5), (1.40) Propiconazole (60207-90-1), (1.41) Prothioconazole (178928-70-6), (1.42) Pyributicarb (88678-67-5), (1.43) Pyrifenox (88283-41-4) (1.44) Quinconazole (103970-75-8), (1.45) Simeconazole (149508-90-7), (1.46) Spiroxamine (118134-30-8), (1.47) Tebuconazole (107534-96-3), (1.48) Terbinafine (91161-71-6), (1.49) Tetraconazole (112281-77-3), (1.50) Triadimefon (43121-43-3), (1.51) Triadimenol (89482-17-7), (1.52) Tridemorph (81412-43-3), (1.53) Triflumizole (68694-11-1), (1.54) Triforine (26644-46-2), (1.55) Triticonazole (131983-72-7), (1.56) Uniconazole (83657-22-1), (1.57) Uniconazole-P (83657-17-4), (1.58) Viniconazole (77174-66-4), (1.59) Voriconazole (137234-62-9), (1.60) 1-(4-Chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol (129586-32-9), (1.61) Methyl 1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate (110323-95-0), (1.62) N'-{5-(Difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylformamidine, (1.63) N-Ethyl-N-methyl-N'-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}formamidine, and (1.64) O-{1-[(4-Methoxyphenoxy)-3,3-dimethylbutan-2-yl}-1H-imidazole-1-thiocarbonate (111226-71-2).

[0138] (2) Respiratory inhibitors (respiratory chain inhibitors): For example, (2.1) bixafen (581809-46-03), (2.2) boscalid (188425-85-6), (2.3) carboxin (5234-68-4), (2.4) diflumetorim (130339-07-0), (2.5) fenfuram (24691-80-3), (2.6) fluopyram (658066-35-4), (2.7) flutolanil (66332-96-5), (2.8) fluxapyroxad (907204-31-3), (2.9) furametpyr (123572-88-3), (2.10) furmecyclox (60568-05-0), (2.11) isopyrazam (mixture of cis-epimeric racemates 1RS,4SR,9RS and trans-epimeric racemates 1RS,4SR,9SR) (88165-58-1), (2.12) isopyrazam (trans-epimeric racemate), (2.13) isopyrazam (trans-epimeric enantiomer 1R,4S,9S), (2.14) isopyrazam (trans-epimeric enantiomer 1S,4R,9R), (2.15) isopyrazam (cis-epimeric racemate 1RS,4SR,9RS), (2.16) isopyrazam (cis-epimeric enantiomer 1R,4S,9R), (2.17) isopyrazam (cis-epimeric enantiomer 1S,4R,9S), (2.18) mepronil (55814-41-0), (2.19) oxycarboxin (5259-88-1), (2.20) penflufen (494793-67-8), (2.21) penthiopyrad (183675-82-3), (2.22) sedaxane (874967-67-6), (2.23) thifluzamide (130000-40-7), (2.24) 1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, (2.25) 3-(Difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide, (2.26) 3-(Difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamide, (2.27) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (1092400-95-7), (2.28) 5,8-Difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine (1210070-84-0) (WO2010025451), (2.29) N-[9-(Dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.30) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide and (2.31) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide.

[0139] (3) Respiratory inhibitors acting on respiratory chain complex III (respiratory chain inhibitors): For example, (3.1) ametoctradin (865318-97-4), (3.2) amisulbrom (348635-87-0), (3.3) azoxystrobin (131860-33-8), (3.4) cyazofamid (120116-88-3), (3.5) coumethoxystrobin (850881-30-0), (3.6) coumoxystrobin (850881-70-8), (3.7) dimoxystrobin (141600-52-4), (3.8) enestroburin (238410-11-2) (WO2004 / 058723), (3.9) famoxadone (131807-57-3) (WO2004 / 058723), (3.10) fenamidone (161326-34-7) (WO2004 / 058723), (3.11) fenoxystrobin (918162-02-4), (3.12) fluoxastrobin (361377-29-9) (WO2004 / 058723), (3.13) kresoxim-methyl (143390-89-0) (WO2004 / 058723), (3.14) metominostrobin (133408-50-1) (WO2004 / 058723), (3.15) orysastrobin (189892-69-1) (WO2004 / 058723), (3.16) picoxystrobin (117428-22-5) (WO2004 / 058723), (3.17) pyraclostrobin (175013-18-0) (WO2004 / 058723), (3.18) pyrametostrobin (915410-70-7) (WO2004 / 058723), (3.19) pyraoxystrobin (862588-11-2) (WO2004 / 058723), (3.20) pyribencarb (799247-52-2) (WO2004 / 058723), (3.21) triclopyricarb (902760-40-1), (3.22) Trifloxystrobin (141517-21-7) (WO2004 / 058723), (3.23) (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide (WO2004 / 058723), (3.24) (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)acetamide (WO2004 / 058723), (3.25) (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}acetamide (158169-73-4), (3.26) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide (326896-28-0), (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) 2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide (119899-14-8), (3.29) 5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, (3.30) (2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}thio)methyl]phenyl}methyl 3-methoxyprop-2-enoate (149601-03-6), (3.31) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide (226551-21-9), (3.32) 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide (173662-97-0) and (3.33) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide (394657-24-0).

[0140] (4) Mitotic and cell division inhibitors: for example (4.1) benomyl (17804-35-2), (4.2) carbendazim (10605-21-7), (4.3) chlorfenazole (3574-96-7), (4.4) diethofencarb (87130-20-9), (4.5) ethaboxam (162650-77-3), (4.6) fluopicolide (239110-15-7), (4.7) fuberidazole (3878-19-1), (4.8) pencycuron (66063-05-6), (4.9) thiabendazole (148-79-8), (4.10) thiophanate-methyl (23564-05-8), (4.11) thiophanate (23564-06-9), (4.12) zoxamide (156052-68-5), (4.13) 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine (214706-53-3) and (4.14) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine (1002756-87-7).

[0141] (5) Compounds capable of multi-site action: for example, (5.1) Bordeaux mixture (8011-63-0), (5.2) captafol (2425-06-1), (5.3) captan (133-06-2) (WO02 / 12172), (5.4) chlorothalonil (1897-45-6), (5.5) copper hydroxide (20427-59-2), (5.6) copper naphthenate (1338-02-9), (5.7) copper oxide (1317-39-1), (5.8) copper oxychloride (1332-40-7), (5.9) copper sulfate (2+) (7758-98-7), (5.10) dichlofluanid (1085-98-9), (5.11) dithianon (3347-22-6), (5.12) dodine (2439-10-3), (5.13) dodine free base, (5.14) ferbam (14484-64-1), (5.15) fluorofolpet (719-96-0), (5.16) folpet (133-07-3), (5.17) guazatine (108173-90-6), (5.18) guazatine acetate, (5.19) iminoctadine (13516-27-3), (5.20) iminoctadine albesilate (169202-06-6), (5.21) iminoctadine triacetate (57520-17-9), (5.22) mancopper (53988-93-5), (5.23) mancozeb (8018-01-7), (5.24) maneb (12427-38-2), (5.25) metiram (9006-42-2), (5.26) metiram zinc (9006-42-2), (5.27) oxine-copper (10380-28-6), (5.28) propamidine (104-32-5), (5.29) propineb (12071-83-9), (5.(30) Sulfur and sulfur preparations, such as calcium polysulphide (7704-34-9), (5.31) thiram (137-26-8), (5.32) tolylfluanid (731-27-1), (5.33) zineb (12122-67-7) and (5.34) ziram (137-30-4).

[0142] (6) Compounds capable of inducing host defense: such as (6.1) acibenzolar-S-methyl (135158-54-2), (6.2) isotianil (224049-04-1), (6.3) probenazole (27605-76-1) and (6.4) tiadinil (223580-51-6).

[0143] (7) Amino acid and / or protein biosynthesis inhibitors: such as (7.1) andoprim (23951-85-1), (7.2) blasticidin-S (2079-00-7), (7.3) cyprodinil (121552-61-2), (7.4) kasugamycin (6980-18-3), (7.5) kasugamycin hydrochloride hydrate (19408-46-9), (7.6) mepanipyrim (110235-47-7), (7.7) pyrimethanil (53112-28-0) and (7.8) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline (861647-32-7) (WO2005070917).

[0144] (8) ATP production inhibitors: such as (8.1) fentin acetate (900-95-8), (8.2) fentin chloride (639-58-7), (8.3) fentin hydroxide (76-87-9) and (8.4) silthiofam (175217-20-6).

[0145] (9) Cell wall synthesis inhibitors: such as (9.1) benthiavalicarb (177406-68-7), (9.2) dimethomorph (110488-70-5), (9.3) flumorph (211867-47-9), (9.4) iprovalicarb (140923-17-7), (9.5) mandipropamid (374726-62-2), (9.6) polyoxins (11113-80-7), (9.7) polyoxorim (22976-86-9), (9.8) validamycin A (37248-47-8), and (9.9) valifenalate (283159-94-4; 283159-90-0).

[0146] (10) Lipid and membrane synthesis inhibitors: such as (10.1) biphenyl (92-52-4), (10.2) chloroneb (2675-77-6), (10.3) dicloran (99-30-9), (10.4) edifenphos (17109-49-8), (10.5) etridiazole (2593-15-9), (10.6) iodocarb (55406-53-6), (10.7) iprobenfos (26087-47-8), (10.8) isoprothiolane (50512-35-1), (10.9) propamocarb (25606-41-1), (10.10) propamocarb-hydrochloride (25606-41-1), (10.11) prothiocarb (19622-08-3), (10.12) pyrazophos (13457-18-6), (10.13) quintozene (82-68-8), (10.14) tecnazene (117-18-0), and (10.15) tolclofos-methyl (57018-04-9).

[0147] (11) Melanin biosynthesis inhibitors: for example, (11.1) carpropamid (104030-54-8), (11.2) diclocymet (139920-32-4), (11.3) fenoxanil (115852-48-7), (11.4) phthalid (27355-22-2), (11.5) pyroquilon (57369-32-1), (11.6) tricyclazole (41814-78-2), and (11.7) 2,2,2-trifluoroethyl {3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate (851524-22-6) (known from WO2005042474).

[0148] (12) Nucleic acid synthesis inhibitors: for example, (12.1) benalaxyl (71626-11-4), (12.2) benalaxyl-M, kiralaxyl (98243-83-5), (12.3) bupirimate (41483-43-6), (12.4) clozylacon (67932-85-8), (12.5) dimethirimol (5221-53-4), (12.6) ethirimol (23947-60-6), (12.7) furalaxyl (57646-30-7), (12.8) hymexazole (10004-44-1), (12.9) metalaxyl (57837-19-1), (12.10) metalaxyl-M, mefenoxam (70630-17-0), (12.11) ofurace (58810-48-3), (12.12) oxadixyl (77732-09-3), and (12.13) oxolinic acid (14698-29-4).

[0149] (13) Signal transduction inhibitors: such as (13.1) chlozolinate (84332-86-5), (13.2) fenpiclonil (74738-17-3), (13.3) fludioxonil (131341-86-1), (13.4) iprodione (36734-19-7), (13.5) procymidone (32809-16-8), (13.6) quinoxyfen (124495-18-7) and (13.7) vinclozolin (50471-44-8).

[0150] (14) Uncoupling agents: such as (14.1) binapacryl (485-31-4), (14.2) dinocap (131-72-6), (14.3) ferimzone (89269-64-7), (14.4) fluazinam (79622-59-6) and (14.5) meptyldinocap (131-72-6).

[0151] (15) Other compounds, such as (15.1) benthiazole (21564-17-0), (15.2) bethoxazin (163269-30-5), (15.3) capsimycin (70694-08-5), (15.4) carvone (99-49-0), (15.5) chinomethionat (2439-01-2), (15.6) pyriofenone (chlazafenone) (688046-61-9), (15.7) cufraneb (11096-18-7), (15.8) cyflufenamid (180409-60-3), (15.9) cymoxanil (57966-95-7), (15.10) cyprosulfamide (221667-31-8), (15.11) dazomet (533-74-4), (15.12) debacarb (62732-91-6), (15.13) dichlorophen (97-23-4), (15.14) diclomezine (62865-36-5), (15.15) difenzoquat (49866-87-7), (15.16) difenzoquat methylsulphate (43222-48-6), (15.17) diphenylamine (122-39-4), (15.18) ecomate, (15.19) fenpyrazamino (473798-59-3), (15.20) flumetover (154025-04-4), (15.21) fluoroimide (41205-21-4), (15.22) flusulfamide (106917-52-6), (15.23) flutianil (304900-25-2), (15.24) fosetyl-aluminium (39148-24-8), (15.25) calcium phosphite, (15.26) sodium phosphite (39148-16-8), (15.27) hexachlorobenzene (118-74-1), (15.28) irumamycin (81604-73-1), (15.29) Methasulfocarb (66952-49-6), (15.30) Methyl isothiocyanate (556-61-6), (15.31) Metrafenone (220899-03-6), (15.32) Mildiomycin (67527-71-3), (15.33) Natamycin (7681-93-8), (15.34) Nickel dimethyldithiocarbamate (15521-65-0), (15.35) Nitrothal-isopropyl (10552-74-6), (15.36) Octhilinone (26530-20-1), (15.37) Oxamocarb (917242-12-7), (15.38) Oxyfenthiin (34407-87-9), (15.39) Pentachlorophenol and its salts (87-86-5), (15.40) Phenothrin, (15.41) Phosphoric acid and its salts (13598-36-2), (15.42) Propamocarb-fosetylate, (15.43) Propanosine-sodium (88498-02-6), (15.44) Proquinazid (189278-12-4), (15.45) Pyrimorph (868390-90-3), (15.45e) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one (1231776-28-5), (15.45z) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one (1231776-29-6), (15.46) Pyroquilon (1018-71-9) (EP-A1 559320), (15.47) Tebufloquin (376645-78-2), (15.48) Tetrachloroisophthalonitrile (76280-91-6), (15.49) Tolnifanide (304911-98-6), (15.50) Triazoxide (72459-58-6), (15.51) Triflumizole (70193-21-4), (15.52) Zoxamide (84527-51-5), (15.(3S,6S,7R,8R)-8-Benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxolan-7-yl 2-methylpropionate (517875-34-2) (known from WO2003035617), (15.54) 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 (1003319-79-6), (15.55) 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 (1003319-80-9), (15.56) 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 (1003318-67-9), (15.57) 1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl 1H-imidazole-1-carboxylate (111227-17-9), (15.58) 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine (13108-52-6), (15.59) 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one (221451-58-7), (15.60) 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone, (15.61) 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 (1003316-53-7), (15.62) 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 (1003316-54-8), (15.63) 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 (1003316-51-5), (15.64) 2-Butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.65) 2-Chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine, (15.66) 2-Phenylphenol and its salts (90-43-7), (15.67) 3-(4,4,5-Trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline (861647-85-0) (known from WO2005070917), (15.68) 3,4,5-Trichloropyridine-2,6-dicarbonitrile (17824-85-0), (15.69) 3-[5-(4-Chlorophenyl)-2,3-dimethyl-1,2-oxazolidin-3-yl]pyridine, (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-sulfonylhydrazide (134-31-6), (15.74) 5-Fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine (1174376-11-4) (known from WO2009094442), (15.75) 5-Fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine (1174376-25-0) (known from WO2009094442), (15.76) 5-Methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, (15.77) (2Z)-3-Amino-2-cyano-3-phenylprop-2-enoic acid ethyl ester, (15.78) N'-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylcarbamimidamide, (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-dichloropyridine-3-carboxamide, (15.82) N-[1-(5-Bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloropyridine-3-carboxamide, (15.83) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodopyridine-3-carboxamide, (15.84) N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide (221201-92-9), (15.85) N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide (221201-92-9), (15.86) N'-{4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-methylformamidine, (15.87) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide (922514-49-6), (15.88) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide (922514-07-6), (15.89) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide (922514-48-5), (15.90) pentyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.91) phenazine-1-carboxylic acid, (15.92) quinolin-8-ol (134-31-6), (15.93) quinolin-8-ol sulfate (2:1) (134-31-6) and (15.94) tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate.

[0152] (16) Other compounds, such as (16.1) 1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (16.2) N-(4'-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (16.3) N-(2',4'-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (16.4) 3-(difluoromethyl)-1-methyl-N-[4'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (16.5) N-(2',5'-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, (16.6) 3-(difluoromethyl)-1-methyl-N-[4'-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (16.7) 5-fluoro-1,3-dimethyl-N-[4'-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (16.8) 2-chloro-N-[4'-(prop-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide, (16.9) 3-(difluoromethyl)-N-[4'-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide, (16.10) N-[4'-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (16.11) 3-(difluoromethyl)-N-(4'-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide, (16.12) N-(4'-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (16.13) 2-chloro-N-(4'-ethynylbiphenyl-2-yl)pyridine-3-carboxamide, (16.14) 2-chloro-N-[4'-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide (known from EP-A1 559 320), (16.15) 4-(difluoromethyl)-2-methyl-N-[4'-(trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide, (16.16) 5-fluoro-N-[4'-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide, (16.17) 2-chloro-N-[4'-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide, (16.18) 3-(difluoromethyl)-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide), (16.19) 5-Fluoro-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide, (16.20) 2-Chloro-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide, (16.21) (5-Bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone, (16.22) N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulfonyl)valinamide (220706-93-4), (16.23) 4-Oxo-4-[(2-phenylethyl)amino]butanoic acid and (16.24) but-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate.

[0153] All of the mixtures of the agents listed under (1) to (16) can optionally form salts with suitable bases or acids, provided that this is possible on the basis of their functional groups.

[0154] They can also be mixed with other known active compounds, such as herbicides, fertilizers, growth regulators, safeners, chemical pheromones, or with agents for improving plant properties.

[0155] When used as insecticides, the active compounds of the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations by mixing with synergists. Synergists are compounds which increase the activity of the active compounds, and the synergists added do not necessarily have to be active themselves.

[0156] When used as insecticides, the active compounds of the invention are also present in their commercially available formulations and in the use forms prepared from these formulations by mixing with inhibitors which reduce the degradation of the active compounds after their application in the habitat of the plants, on the surfaces of the plant parts or in the plant tissue.

[0157] All plants and parts thereof can be treated in accordance with the present invention. The term "plant" in the present invention is to be understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants obtained by conventional breeding and selection methods or by biotechnological and genetic engineering methods or by a combination of the foregoing methods, including transgenic plants and plant cultivars, whether or not protected by plant breeders’ rights. Parts of plants are to be understood as meaning all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, trunks, flowers, fruiting bodies, fruits, seeds, roots, tubers and rhizomes. The plant parts also include harvestable material, as well as asexual and sexual propagation material, such as cuttings, tubers, rhizomes, branches and seeds.

[0158] The treatment of plants and parts thereof with the active compounds according to the invention is effected directly by conventional treatment methods or by allowing the compounds to act on the environment, habitat or storage space, said conventional treatment methods being, for example, drenching, spraying, evaporation, atomizing, broadcasting, painting, injection, and, in the case of propagation material, especially seeds, also coating with one or more layers.

[0159] As mentioned above, all plants and their parts can be treated in accordance with the invention. In a preferred embodiment, wild plant varieties and plant cultivars, or plant varieties and plant cultivars obtained by conventional biotechnological breeding methods such as crossing or protoplast fusion, and parts thereof are treated. In another preferred embodiment, transgenic plants and plant cultivars (Genetically Modified Organisms) obtained by genetic engineering, if appropriate in combination with conventional methods, and parts thereof are treated. The terms "part", "part of a plant" or "plant part" are as defined above.

[0160] More preferably, the plants to be treated according to the invention are plant cultivars which are commercially available or in use. The term "plant cultivar" is to be understood as meaning plants having new properties ("characteristics") obtained by conventional breeding, mutagenesis or recombinant DNA techniques. They can be cultivars, biotypes or genotypes.

[0161] Depending on the plant variety or cultivar, its location of cultivation and the growth conditions (soil, climate, vegetative period of the plant, nutrition), the treatment according to the invention can also produce supra-additive (“synergistic”) effects. This can result in effects that exceed the normal expectations, such as a reduction in the application rates of the compounds and compositions used according to the invention and / or an extension of their spectrum of action and / or an increase in their activity, improvement of the growth of the plants, an increase in the tolerance to high or low temperatures, an increase in the tolerance to drought or to the salt content in water or in the soil, an improvement of the flowering quality, easier harvesting, acceleration of ripening, an increase in the harvest yield, an increase in the quality of the harvested product and / or an improvement of its nutritional value, an improvement of the storage properties of the harvested product and / or its processability.

[0162] Preferred transgenic plants or plant cultivars processed according to the invention (i.e., those obtained by genetic engineering) include all plants that have received genetic material in the genetic modification, which confers particularly advantageous useful properties ("traits") on the plants. Examples of such traits are improved plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to salt content in water or soil, improved flowering quality, easier harvesting, accelerated ripening, increased harvest yield, improved quality of the harvested product and / or its nutritional value, improved storage properties of the harvested product and / or its processability. Other examples of traits particularly emphasized are improved resistance of the plants to animal and microbial pests, such as resistance to insects, mites, phytopathogenic fungi, bacteria and / or viruses, and increased tolerance of the plants to certain herbicidally active compounds. Examples of transgenic plants that may be mentioned are important crop plants, such as cereals (wheat, rice), maize, soybeans, potatoes, sugar beets, tomatoes, peas and other vegetable varieties, cotton, tobacco, oilseed rape and fruit plants (fruits being apples, pears, citrus fruits and grapes), with particular emphasis on maize, soybeans, potatoes, cotton, tobacco and oilseed rape. Particularly emphasized traits are increased resistance of the plants to insects, arachnids, nematodes, slugs and snails by toxins formed in the plants, in particular by genetic material of Bacillus thuringiensis (e.g., by genes CryⅠA(a), CryⅠA(b), CryⅠA(c), CryⅡA, CryⅢA, CryⅢB2, Cry9c, Cry2Ab, Cry3Bb and CryⅠF and their combinations; hereinafter simply referred to as "Bt plants") formed in the plants. Also particularly emphasized traits are increased resistance of the plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and the corresponding expressed proteins and toxins. In addition, particularly emphasized traits are increased tolerance of the plants to certain herbicidally active compounds such as imidazolinones, sulfonylureas, glyphosate or phosphinothricin (e.g., the "PAT" gene). The genes conferring the desired traits may also be present in combination with each other in the transgenic plants. Examples of "Bt plants" that may be mentioned are commercially available under the trade name YIELD (e.g., maize, cotton, soybeans), (e.g., maize), (e.g., maize), (cotton), (cotton) and (potato) maize varieties, cotton varieties, soybean varieties and potato varieties. Examples of herbicide-tolerant plants that may be mentioned are commercially available under the trade name Roundup (With glyphosate tolerance, such as maize, cotton, soybean), Liberty (With glufosinate tolerance, such as rape), (With imidazolinone tolerance) and (With sulfonylurea tolerance, such as maize) maize varieties, cotton varieties and soybean varieties. Herbicide-resistant plants (plants bred in a conventional herbicide-tolerant manner) that can be mentioned include commercially available varieties (such as maize) named . Of course, the above description also applies to plant cultivars with the said genetic characteristics or genetic characteristics to be developed, which plants will be developed and / or marketed in the future.

[0163] The above plants can be treated in a particularly advantageous manner with the compounds of general formula (I) according to the invention or the mixtures of active compounds according to the invention. The preferred ranges of the above active compounds or mixtures also apply to the treatment of the said plants. Particular emphasis is placed on the treatment of plants with the compounds or mixtures specifically proposed according to the invention.

[0164] The active compounds according to the invention are active not only against pests in plants, hygiene pests and pests in stored products, but also against parasites (ectoparasites and endoparasites) of animals in the veterinary field, such as hard ticks, soft ticks, sarcoptic mites, spider mites, flies (biting and sucking), fly larvae, lice, chewing lice, bird lice and fleas. The said parasites include:

[0165] Order Anoplurida, such as Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

[0166] Order Mallophagida and suborders Amblycerina and Ischnocerina, such as Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. and Felicola spp.

[0167] Diptera and Nematocerina and Brachycerina, such as Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., and Melophagus spp.

[0168] Siphonapterida, such as Pulex spp., Ctenocephalides spp., Xenopsylla spp., and Ceratophyllus spp.

[0169] Heteropterida, such as Cimex spp., Triatoma spp., Rhodnius spp., and Panstrongylus spp.

[0170] Order Blattarida, such as Blatta orientalis, Periplaneta americana, Blattela germanica, and Supella spp.

[0171] Subclass Acaria (or Acarina) and orders Metastigmate and Mesostigmata, such as Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., and Varroa spp.

[0172] The Actinedida (Prostigmata) and Acaridida (Astigmata), such as Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

[0173] The active compounds of formula (I) according to the invention are also suitable for controlling arthropods which infest the following animals: agricultural livestock, such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, domestic chickens, turkeys, ducks, geese and bees, other pets, such as dogs, cats, caged birds and ornamental fish, and laboratory animals, such as hamsters, guinea pigs, rats and mice. Controlling said arthropods is intended to reduce mortality and the reduction of production (meat, milk, wool, skin, eggs, honey, etc.), so that livestock farming becomes more economical and easier by using the active compounds according to the invention.

[0174] The active compounds according to the invention are used in the veterinary field and in livestock farming in a known manner, and the administration forms are: enteral administration by means of, for example, tablets, capsules, drinks, veterinary boluses, granules, ointments, pills, feed-through methods and suppositories; parenteral administration by means of, for example, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implantation; nasal administration; skin administration in the form of, for example, dipping or bathing, spraying, pouring and spotting, washing and dusting, and by means of shaped articles comprising the active compound, such as collars, ear tags, tail tags, limb bands, halters, markers, etc.

[0175] When used for livestock, poultry, domestic animals, etc., the active compounds of formula (I) can be used directly as a preparation (e.g., powder, emulsion, flowable agent) containing the active compound in an amount of 1 to 80% by weight, or can be used after dilution 100 to 10,000 times, or can be used in the form of a chemical bath.

[0176] Moreover, it has also been found that the compounds of the present invention have a strong insecticidal effect against insects that damage industrial materials.

[0177] The following insects can be mentioned as examples, preferably but not restrictively:

[0178] Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinuspecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctusplanicollis, Lyctus linearis, Lyctus pubescens, Trogoxylonaequale, Minthes rugicollis, Xyleborus spec., Tryptodendronspec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec., Dinoderusminutus;

[0179] Dermapterans, such as Sirex juvencus, Urocerusgigas, Urocerus gigas taignus, Urocerus augur;

[0180] Termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;

[0181] Bristletails, such as Lepisma saccharina.

[0182] In the present invention, the meaning of industrial materials should be understood as inanimate materials, for example, preferably plastics, adhesives, sizing agents, paper and board, leather, wood and processed wood products, and coating compositions.

[0183] The ready-to-use compositions may also optionally contain other insecticides and, optionally, may also contain one or more fungicides.

[0184] In addition, the compounds of the present invention can be used to protect objects in contact with salt water or brackish water, in particular ship hulls, sieves, nets, buildings, mooring equipment and signal systems, against fouling.

[0185] In addition, the compounds of the present invention can be used alone or in combination with other active compounds as antifouling compositions.

[0186] The active compounds of the present invention are also suitable for controlling animal pests in the household field, hygiene and protection of stored products, in particular insects, arachnids and mites found in enclosed spaces, such as dwellings, factory workshops, offices, vehicle cabins, etc. They can be used alone or in combination with other active compounds and auxiliaries in household insecticidal products for controlling said pests. They are effective against sensitive and resistant species and all developmental stages.

[0187] The pests include:

[0188] Scorpionidea, such as Buthus occitanus.

[0189] Order Acarina, such as Argas persicus, Argas reflexus, Bryobia spp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.

[0190] Order Araneae, such as Aviculariidae, Araneidae.

[0191] Order Opiliones, such as Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.

[0192] Order Isopoda, such as Asellus aquaticus, Armadillidium vulgare.

[0193] Order Diplopoda, such as Blaniulus guttulatus, Polydesmus spp.

[0194] Order Chilopoda, such as Geophilus spp.

[0195] Order Zygentoma, such as Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.

[0196] Blattodea, such as Blatta orientalis, Blattella germanica, Blattella asahinai, Blaberus discoidalis, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

[0197] Saltatoria, such as Acheta domesticus.

[0198] Dermaptera, such as Forficula auricularia.

[0199] Isoptera, such as Kalotermes spp., Reticulitermes spp.

[0200] Psocoptera, such as Lepinatus spp., Liposcelis spp.

[0201] Coleoptera, such as Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.

[0202] Diptera, such as Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.

[0203] Lepidoptera, such as Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.

[0204] Siphonaptera, such as Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.

[0205] Hymenoptera, such as Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum,

[0206] Anoplura, such as Pediculus humanus capitis, Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix, Phthirus pubis.

[0207] Heteroptera, such as Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

[0208] In the field of household insecticides, they can be used alone or in combination with other suitable active compounds, such as phosphates, carbamates, pyrethroids, neonicotinoids, growth regulators or active compounds from other known classes of insecticides.

[0209] They are used in the following forms of products: aerosol, pressure-free spray products such as pump and atomizer sprays, automatic misting systems, smoke agents, foam agents, gel agents, evaporation products with evaporator tablets made of cellulose or plastic, liquid evaporants, gel and film evaporants, propellant-driven evaporants, energy-free or passive evaporation systems, moth papers, moth bags or moth glues, and as granule or powder agents in baits for spreading or in bait stations. Detailed Description of the Invention

[0210] The following examples are used to illustrate the present invention and should not be regarded as limiting the present invention in any way. The scope of the rights claimed by the present invention is defined by the claims.

[0211] In view of the economy and diversity of the compounds, we preferably synthesized some compounds. Among the many synthesized compounds, some are listed in Table 1 below. The specific compound structures and the corresponding compound information are shown in Table 1. The compounds in Table 1 are only for better illustrating the present invention, but do not limit the present invention. For those skilled in the art, this should not be understood as the scope of the above-mentioned subject matter of the present invention being limited to the following compounds.

[0212] Table 1 Compound Structures and 1 H NMR Data

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221] Table A has the same structure as Table 1 above, except that the general formula I is replaced with the general formula I' having a chiral center (When n in General Formula I is 1), and in Table A, the entries under the column heading "Serial Number" are successively described as 16(R)-18(R), 23(R), 26(R), 28(R), 89(R), 91(R)-94(R), 96(R), 98(R), 101(R)-102(R), 104(R), 106(R)-108(R), 110(R), 112(R)-114(R), 116(R), 118(R)-121(R), 123(R)-124(R), 126(R). For example, 16(R) corresponds to the compound with the R configuration at the S* position described in Compound 16 in Table 1.

[0222] Several methods for preparing the compounds of the present invention are described in detail in the following schemes and examples. The starting materials can be purchased on the market or can be prepared by methods known in the literature or as described in detail. Those skilled in the art should understand that the compounds of the present invention can also be synthesized using other synthetic routes. Although specific starting materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar starting materials and conditions, and various isomers of the compounds resulting from such modifications or variations of the preparation method of the present invention are included within the scope of the present invention. In addition, the preparation methods described below can be further modified according to the disclosure of the present invention using conventional chemical methods well-known to those skilled in the art. For example, protecting appropriate groups during the reaction, etc.

[0223] The method examples provided below are used to facilitate a further understanding of the preparation methods of the present invention. The specific substances, types, and conditions used are determined to further illustrate the present invention and are not a limitation of its reasonable scope. The reagents used in the synthesis of the compounds in the following table can either be purchased on the market or can be easily prepared by ordinary technicians in the art.

[0224] Examples of representative compounds are as follows. The synthesis methods of other compounds are similar and will not be described in detail here.

[0225] 1. Synthesis of Compound 7

[0226] Dissolve Compound 7-1 (150 mg, 1 eq) in 20 mL of solvent (dioxane:water = 10:1), successively add 7-2 (145 mg, 1.2 eq), potassium carbonate (205 mg, 3 eq), and 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium(II) dichloromethane complex (30 mg, 0.02 eq), protect with nitrogen, heat to 100 °C, stir overnight, monitor the reaction to completion, extract with water and ethyl acetate 3 times, combine the organic phases, dry, concentrate, mix the samples, and purify by normal phase to obtain Compound 7 (100 mg, yield 60%, white solid).

[0227]

[0228] 2. Synthesis of Compound 14

[0229] (1) Add Compound 14-1 into a 100 mL eggplant-shaped flask, dissolve it with DMF, add 3.0 eq potassium dihydrogen phosphate, 3.0 eq potassium carbonate, 3.0 eq sodium dithionite and 2.0 eq Compound 14-2. Heat the mixture to 40 °C and react for 2 h. After suction filtration, add water and ethyl acetate to the filtrate for extraction, wash it three times with saturated brine, dry the organic phase, and purify it through a normal-phase column to obtain oily Compound 14-3 (yield 65%).

[0230]

[0231] (2) Dissolve Compound 14-3, 3.0 eq potassium carbonate, 1.5 eq 7-2 and 0.05 eq dichloromethane complex of [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride in 30 mL dioxane, add 3 mL water, displace the air with nitrogen three times, heat the mixture to 100 °C and react overnight. After monitoring the reaction to completion, directly mix the sample for purification and purify it through a normal-phase column to obtain white solid Compound 14 (yield 22%).

[0232]

[0233] 3. Synthesis of Compound 16

[0234] Dissolve Compound 7 (100 mg, 1 eq) in dichloromethane, add m-chloroperoxybenzoic acid (47 mg, 0.8 eq), stir at room temperature for 1 h. After monitoring the reaction to completion, wash it three times with saturated aqueous sodium bicarbonate solution, take the organic phase, dry, concentrate, mix the sample, and purify it through normal-phase to obtain Compound 16 (100 mg, 77%, white solid).

[0235]

[0236] 4. Synthesis of Compound 20

[0237] Dissolve 150 mg of Compound 7 in dichloromethane, add m-chloroperoxybenzoic acid (10 eq), stir at room temperature for 24 h. After monitoring the reaction to completion, wash it three times with saturated aqueous sodium bicarbonate solution, take the organic phase, dry, concentrate, mix the sample, and purify it through normal-phase to obtain Compound 20 (120 mg, yield 73%, white solid).

[0238]

[0239] 5. Synthesis of Compound 22

[0240] (1) Dissolve 2.9 g of raw material 22-1 in DMF, add 2 equivalents of cyclopropyl bromomethane, and react at room temperature for 2 hours. After monitoring the completion of the reaction, add water to quench the reaction, add EA, wash the organic phase twice with water and twice with saturated brine, dry over anhydrous sodium sulfate, and then rotary evaporate to obtain the crude white solid 22-2 (3.1 g, 86% yield).

[0241]

[0242] (2) Under the condition of an oil bath, dissolve compound 22-2 (3.1 g, 1 eq) in 50 mL of a mixed solution (concentrated HCl:EtOH = 1:5), and stir at 60 °C overnight. After monitoring the end of the reaction, concentrate to obtain the crude compound 22-3 (2.6 g, 99% yield).

[0243]

[0244] (3) Dissolve 300 mg of compound 22-3 in 5 mL of acetonitrile, add 2 equivalents of copper bromide, 2 equivalents of cuprous bromide, and 2 equivalents of tert-butyl nitrite under an ice bath, react at room temperature for 2 h, monitor the completion of the reaction, rotary evaporate the solvent, add EA and water for extraction, combine the organic phases, dry, and rotary evaporate to obtain 400 mg of the crude product of brown liquid compound 22-4.

[0245]

[0246] (4) Dissolve 200 mg of compound 22-4 in 5 mL of 1,4-dioxane and 0.5 mL of water, add 1 equivalent of 7-2, 0.03 equivalent of Pd(dppf)Cl 2 、3 equivalents of Cs 2 CO 3 , under nitrogen protection, react at 100 °C overnight. After monitoring the completion of the reaction, rotary evaporate and mix the sample, purify by normal-phase column chromatography to obtain the yellow oily compound 22 (150 mg, 67% yield).

[0247]

[0248] 6. Synthesis of compound 30

[0249] (1) Add compound 7-1 (150 mg, 1 eq), potassium acetate (145 mg, 3 eq), catalyst (CAS No.: 95464-05-4) (12 mg, 0.03 eq), 30-1 (188 mg, 1.5 eq), and 20 mL of 1,4-dioxane to a flask, under nitrogen protection, react at 100 °C overnight, and directly use the reaction solution for the next step of the reaction after the reaction is completed.

[0250]

[0251] (2) Potassium carbonate (205 mg, 3 eq), 30-3 (164 mg, 1.5 eq), catalyst (CAS No.: 95464-05-4) (12 mg, 0.03 eq), and a mixed solvent of 1,4-dioxane:H 2 O = 10:1 (22 ml) were directly added to the system, and the reaction was carried out overnight at 100 °C under nitrogen protection. After the reaction was completed, the sample was directly purified by stirring to obtain 40 mg of compound 30 (total yield 22%).

[0252]

[0253] 7. Synthesis of compound 100

[0254] At room temperature, compound 30-2 (200 mg, 0.57 mmol) was dissolved in a mixed solvent (20 ml of 1,4-dioxane, 2 mL of H 2 O), and compound 100-1 (156 mg, 0.68 mmol), potassium carbonate (235 mg, 1.71 mmol), and Pd(dppf)Cl 2 (25 mg, 0.03 mmol) were added. The reaction solution was placed under nitrogen protection and reacted at 100 °C for 4 h until the reaction was completed. The reaction solution was poured into water to quench the reaction, extracted three times with ethyl acetate, the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and stirred with the sample, and purified by normal phase chromatography to obtain compound 100 (32 mg, yield 15%).

[0255]

[0256] 8. Synthesis of compound 104

[0257] Compound 14 (80 mg, 0.22 mmol) was dissolved in 20 ml of DCM, and m-CPBA (50 mg, 0.24 mmol) was added under an ice bath. The mixture was stirred at room temperature for 2 h, and the reaction was monitored by TLC to be complete. Water was added to the reaction solution, and the mixture was extracted three times with dichloromethane. The organic phases were combined, washed three times with saturated sodium chloride solution, dried and concentrated. Silica gel column chromatography was used to obtain white solid compound 104 (70 mg, yield 84%).

[0258]

[0259] Biological activity evaluation:

[0260] Dissolve the compound of the present invention in acetone and then dilute it with clear water into liquid medicines with different concentration (ppm) gradients. Place peanut leaves in a petri dish, and then use a spray tower for spraying. After spraying, open the lid of the petri dish and let it dry completely at room temperature. Then, put 15 adult Tetranychus truncatus, adult Tetranychus cinnabarinus, and adult Tetranychus urticae into each dish respectively. Each peanut leaf is one replicate, and each treatment is replicated 3 times. Use clear water as a control. After applying the medicine, transfer them to the feeding conditions for feeding. Check the number of dead insects after 48 h, and calculate the mortality rate according to the formula: Mortality rate (%) = (Number of dead insects / Number of tested insects) * 100.

[0261] Table 2 Representative acaricidal test results

[0262]

[0263] Note: N represents no data; Control compound A: Control compound B:

[0264]

[0265] The compound of the present invention has satisfactory insecticidal and / or acaricidal activities against animal pests, especially when applied at a relatively low application rate, and has high selectivity and improved compatibility in useful plant crops.

Claims

1. A pyrazole-substituted aryl sulfide compound, the general formula of which is shown in I: in, X is a halogen; Y is hydrogen, halogen, nitro, cyano, hydroxyl, mercapto, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, -OR 11 or -S(O) n R 11 ; Z is an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, wherein the "alkyl", "alkenyl" or "alkynyl" is optionally selected from halogen, cycloalkyl, cycloalkenyl, aryl, heterocyclyl, hydroxyl, mercapto, -OR 11 or -S(O) n R 11 At least one group in is substituted; R1 is hydrogen, amino, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, aryl, heterocyclylalkyl or arylalkyl; R2 and R3 are independently hydrogen, halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl or -OR 11 ; R 11 is alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl; The aforementioned "cycloalkyl", "cycloalkenyl", "heterocyclyl" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted by alkyl, -OR 10 、-SR 10 、-(CO)OR 10 、-(SO2)R 10 、-N(R 10 )2 or -O-alkylene-(CO)OR 10 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; R 10 are independently 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; n is 0, 1 or 2.

2. The pyrazole-substituted aryl sulfide compound according to claim 1, characterized in that: Y is hydrogen, halogen, nitro, cyano, hydroxyl, mercapto, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, -OR 11 or -S(O) n R 11 ; Z is C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl or heterocyclyl, wherein the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally selected from halogen, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, heterocyclyl, hydroxyl, thiol, -OR 11 or -S(O) n R 11 At least one group in is substituted; R1 is hydrogen, amino, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, heterocyclyl, aryl, heterocyclylC1-C8 alkyl or arylC1-C8 alkyl; R2 and R3 represent independently hydrogen, halogen, 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 or -OR 11 ; R 11 is 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 cycloalkenyl, aryl or heterocyclyl; The aforementioned "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl", "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, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR 10 、-SR 10 、-(CO)OR 10 、-(SO2)R 10 、-N(R 10 )2 or -O-(C1-C8 alkylene)-(CO)OR 10 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; R 10 They are independently 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. The pyrazole-substituted aryl sulfide compound according to claim 1 or 2, characterized in that: Y is hydrogen, halogen, nitro, cyano, hydroxyl, mercapto, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, -OR 11 or -S(O) n R 11 ; Z is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl or heterocyclyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is optionally selected from halogen, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclyl, hydroxyl, thiol, -OR 11 or -S(O) n R 11 1 to 3 groups are substituted; R1 is hydrogen, amino, 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, aryl, heterocyclylC1-C6 alkyl or arylC1-C6 alkyl; R2 and R3 represent independently hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl or -OR 11 ; R 11 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl or heterocyclic; The aforementioned "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "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, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR 10 、-SR 10 、-(CO)OR 10 、-(SO2)R 10 、-N(R 10 )2 or -O-(C1-C6 alkylene)-(CO)OR 10 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; R 10 are independently hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl, or phenyl substituted by 1 to 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy; Preferably, the compound is selected from any one of Table 1 and Table A in the specification.

4. A pyrazole-substituted aryl sulfide compound represented by formula I': in, The sulfur atom is a chiral center, and the substituents R1, R2, R3, X, Y and Z are defined as in any one of claims 1 to 3; In terms of stereoisomer content based on sulfur atoms having R and S configurations, it has a stereochemical purity of 60-100% (R), preferably 70-100%, more preferably 80-100%, further preferably 90-100%, and further preferably 95-100%.

5. The method for preparing the pyrazole-substituted aryl sulfide compound according to any one of claims 1 to 4, comprising the following steps: (1) when n represents 0, compound II and compound III or compound IV and compound V undergo substitution reaction to obtain compound I-1; (2) When n represents 1 or 2, compound I-1 is oxidized to obtain compound I-2 or compound I-3; The chemical reaction equation is: in, Hal represents halogen, preferably Br, Q represents The other substituents R1, R2, R3, X, Y and Z are as defined in any one of claims 1-4.

6. The method for preparing the pyrazole-substituted aryl sulfide compound according to claim 5, characterized in that: The step (1) is carried out in the presence of a solvent; preferably, a catalyst and / or a base is added in the step (1); more preferably, the solvent is selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane, tetrahydrofuran, toluene, ethyl acetate or water, the base is selected from at least one of an inorganic base or an organic base, and the catalyst is selected from at least one of Pd(dppf)Cl2, Pd(PPh3)4, PdCl2, Pd(OAc)2, Pd(PPh3)2Cl2, NiCl2(dppf) and PdCl2(dppf)·CH2Cl2; The step (2) is carried out in the presence of an oxidant and a solvent; preferably, the oxidant is selected from at least one of meta-chloroperbenzoic acid, H2O2, NaClO or KMnO4; preferably, the solvent is selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane, tetrahydrofuran, toluene, ethyl acetate or water.

7. A mite-killing composition, characterized in that: The invention comprises a biologically effective amount of at least one of the pyrazole-substituted aryl sulfide compounds according to any one of claims 1 to 4; preferably, it also comprises a formulation adjuvant; more preferably, it also comprises other active ingredients.

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

9. Use of the pyrazole-substituted aryl sulfide compound according to any one of claims 1 to 4 or the composition according to claim 7 in controlling mites.

10. An intermediate, which is as shown in compound II, III, IV or V in claim 5.

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