Pyrazole-substituted aryl sulfide compound and use thereof

Abstract

The present invention belongs to the technical field of pesticides, and particularly relates to a pyrazole-substituted aryl sulfide compound and the use thereof. The compound has a general formula as shown in (I), wherein X is halogen, Y is hydrogen, halogen, nitro, cyano, etc., Z is alkyl, alkenyl, alkynyl, cycloalkyl, etc., R1 is hydrogen, amino, alkyl, alkenyl, alkynyl, haloalkyl, etc., and R2 and R3 are independently hydrogen, halogen, alkyl, alkenyl, alkynyl, etc. The compound has an excellent acaricidal activity.

Description

A pyrazole-substituted aryl sulfide compound and its application Technical Field

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

[0002] In the agricultural and horticultural fields, crop damage caused by pests remains severe, and due to the emergence of pests resistant to existing agents, there is a growing demand for novel agricultural and horticultural insecticides and acaricides. The increasing number of elderly people employed in agriculture has led to a demand for labor-saving application methods, and there is also a need for agricultural and horticultural insecticides and acaricides with properties suitable for these application methods. Summary of the Invention

[0003] In order to solve the above problems existing in the prior art, the present invention provides a pyrazole-substituted aryl sulfide compound having excellent acaricidal activity.

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

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

[0006] wherein X is a halogen;

[0007] Y is hydrogen, halogen, nitro, cyano, hydroxyl, mercapto, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, -OR 11 or -S(O) n R 11 ;

[0008] Z is an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclic group, wherein the "alkyl", "alkenyl" or "alkynyl" is optionally selected from halogen, cycloalkyl, cycloalkenyl, aryl, heterocyclic group, hydroxyl, mercapto, -OR 11 or -S(O) n R 11 At least one group in is substituted;

[0009] R1 is hydrogen, amino, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, aryl, heterocyclylalkyl, or arylalkyl;

[0010] R2 and R3 are independently hydrogen, halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl or -OR 11 ;

[0011] R11 is alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkenyl, aryl, or heterocyclyl;

[0012] 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 fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-;

[0013] 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;

[0014] n is 0, 1, or 2.

[0015] In one embodiment, Y is hydrogen, halogen, nitro, cyano, hydroxyl, thiol, 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 ;

[0016] 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;

[0017] R1 is hydrogen, amino, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, heterocyclyl, aryl, heterocyclylC1-C8 alkyl or arylC1-C8 alkyl;

[0018] 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 ;

[0019] R 11 is a C1-C8 alkyl group, a C2-C8 alkenyl group, a C2-C8 alkynyl group, a halogenated C1-C8 alkyl group, a halogenated C2-C8 alkenyl group, a halogenated C2-C8 alkynyl group, a C3-C8 cycloalkyl group, a C3-C8 cycloalkenyl group, an aryl group, or a heterocyclic group;

[0020] 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 fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-;

[0021] R 10 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.

[0022] In another embodiment, Y is hydrogen, halogen, nitro, cyano, hydroxyl, thiol, 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 ;

[0023] 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;

[0024] 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;

[0025] 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 ;

[0026] R 11 is a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a halo-C1-C6 alkyl group, a halo-C2-C6 alkenyl group, a halo-C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C3-C6 cycloalkenyl group, an aryl group, or a heterocyclic group;

[0027] 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(R10 )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-;

[0028] R 10 Each of them is independently hydrogen, C1-C6 alkyl, halo-substituted C1-C6 alkyl, phenyl, or phenyl substituted by 1 to 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo-substituted C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo-substituted C1-C6 alkoxy.

[0029] In the definition of the compounds represented by the above general formula and in all the following structural formulas, the technical terms used, whether used alone or in compound words, represent the following substituents: Alkyl groups with more than two carbon atoms can be straight-chain or branched. For example, the compound word "-O-alkylene-(CO)OR 10 " " in which the alkylene group can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. The alkyl group is, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such as n-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl, tert-butyl or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, alkenyl 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. The term "cycloalkyl" refers to a group consisting of cyclopentyl, cyclohexyl, cyclopentenyl, cyclohex ...

[0030] Unless otherwise specified, the "aryl" mentioned 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 etc., and also include but are not limited to heteroaryl, i.e. an aromatic cyclic group containing, for example, 3 to 6 ring atoms and optionally fused to a benzo ring, wherein 1 to 4 (e.g. 1, 2, 3 or 4) heteroatoms in the ring atoms are selected from oxygen, nitrogen and sulfur, for example

[0031] If a group is substituted by a group, this is understood to mean that the group is substituted by one or more identical or different groups selected from the groups mentioned. Furthermore, identical or different substituent characters contained in identical or different substituents are independently selected and may be identical or different. The same applies to ring systems formed from different atoms and units. At the same time, compounds known to those skilled in the art to be chemically unstable under standard conditions are excluded from the scope of the claims.

[0032] In addition, unless otherwise specified, the term "substituted by at least one group" as used herein refers to being substituted by 1, 2, 3, 4 or 5 groups; groups (including heterocyclic groups, aryl groups, etc.) without a specific connection position 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 complies with the chemical bond connection rules. For example, a heteroaryl group substituted by 1 methyl group Can represent wait.

[0033] The present invention also provides a pyrazole-substituted aryl sulfide compound as shown in Formula I':

[0034] wherein the sulfur atom is a chiral center, and the substituents R1, R2, R3, X, Y and Z are as defined above;

[0035] 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 even more preferably 95-100%.

[0036] Here, "stereochemical purity" refers to the percentage of the amount of the stereoisomer in question to the total amount of stereoisomers having a chiral center.

[0037] In the present invention, the stereochemical configuration at the position marked * in Formula I is determined according to the Cahn-Ingold-Prelog system to be predominantly (R), however, the subject matter of the present invention also relates to all stereoisomers at other positions encompassed by Formula I, and mixtures thereof. Such compounds of Formula I may contain, for example, one or more additional asymmetric carbon atoms or other double bonds not specifically described in Formula I. It should be understood that the present invention includes pure isomers and mixtures thereof enriched to varying degrees in pure isomers, wherein the asymmetric carbon atom at the position marked * is in the R-configuration, or in mixtures in which compounds or compounds of the same chemical structure have the R-configuration at the position marked *, or are present in a proportion in which the compound having 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 be resolved to varying degrees. As long as the stereochemical configuration conditions at the positions marked with * are met, possible stereoisomers defined by specific spatial forms, such as enantiomers, diastereomers, Z- and E-isomers, are included in Formula I and can be obtained from mixtures of stereoisomers using conventional methods or can be prepared by stereoselective reactions combined with the use of stereochemically pure starting materials.

[0038] If various functional groups are present, the present invention also includes any keto and enol tautomeric forms and mixtures and salts thereof.

[0039] Stereoisomers can be obtained from the mixture obtained in the preparation by optical resolution. Stereoisomers can also be selectively prepared by using stereoselective reactions and optically active starting materials and / or auxiliary agents. For optical resolution, conventional methods (see Textbooks of Stereochemistry) can usually be used, such as the following methods for separating the mixture into diastereomers, such as physical methods, such as crystallization, chromatography, especially column chromatography and high pressure liquid chromatography, optionally distillation methods under reduced pressure, extraction methods and other methods, usually using chromatographic separation on a chiral solid phase, which can separate the residual mixture of enantiomeric structures. Suitable for preparation or for industrial scale is such a method, such as crystallization of diastereomeric salts, which can be obtained from compounds using optically active acids, and if an acidic group is present, optically active bases can be used as needed.

[0040] The present invention also provides a method for preparing a pyrazole-substituted aryl sulfide compound, comprising the following steps:

[0041] (1) When n represents 0, compound II and compound III or compound IV and compound V undergo a substitution reaction to prepare compound I-1;

[0042] (2) When n represents 1 or 2, compound I-1 is oxidized to obtain compound I-2 or compound I-3;

[0043] The chemical reaction equation is:

[0044] Wherein, Hal represents halogen, preferably Br, and Q represents The other substituents R1, R2, R3, X, Y and Z are as defined above.

[0045] In one embodiment, the step (1) is performed in the presence of a solvent.

[0046] In another embodiment, a catalyst and / or a base is added in step (1).

[0047] In another specific embodiment, the base in step (1) is selected from at least one of an inorganic base (such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KHCO3, KF, CsF, KI, NaI, K3PO4, K2HPO4, NaOH, KOH, NaH, KH, etc.) or an organic base (such as pyrazole, triethylamine, DIEA, potassium trimethylsilanolate, AcOK, AcONa, MeONa, EtONa, t-BuONa, etc.).

[0048] In another specific embodiment, the catalyst in step (1) 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 (CAS No.: 95464-05-4).

[0049] In one embodiment, step (2) is performed in the presence of an oxidizing agent and a solvent.

[0050] In another specific embodiment, the oxidant in step (2) is selected from at least one of m-chloroperbenzoic acid, H2O2, NaClO or KMnO4.

[0051] In another specific embodiment, the solvents in steps (1) and (2) are respectively selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane, tetrahydrofuran, toluene, ethyl acetate or water.

[0052] The present invention also provides an intermediate, which is shown as compound II, III, IV or V.

[0053] Due to their 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, particularly insects, arachnids, worms, nematodes, and mollusks encountered in agriculture, horticulture, animal husbandry, forestry, parks and leisure facilities, protecting stored products and materials, and in the health sector. They can be preferably used as plant protection agents. They are active against normally sensitive and resistant species and all or some developmental stages. These pests include:

[0054] From the order of the Anoplura (Phthiraptera), for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.

[0055] From the order Arachnida, for example, 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.

[0056] Bivalve Molluscs (Bivalva), for example, Dreissena spp.

[0057] From the order of the Chilopoda, for example, Geophilus spp., Scutigera spp.

[0058] From the order of the Coleoptera, for example, Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Agelasta 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.), potato beetles (Leptinotarsa ​​decemlineata), Leucoptera spp., Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp., Lyctus spp., Megascelis spp., Melanotus spp., Meligethes aeneus, Melolontha spp., Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorrhynchus spp., Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllotreta spp., Popillia japonica, Premnotrypes spp., Psylliodes spp., Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Sternechus spp., Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tribolium spp.), Trogoderma spp., Tychius spp., Xylotrechus spp., and Zabrus spp.

[0059] From the order of the Collembola, for example, Onychiurus armatus.

[0060] From the order of the Diplopoda, for example, Blaniulus guttulatus.

[0061] From the order of the Diptera, for example, 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., carrot stem fly (Psila rosae), Rhagoletis spp., Stomoxys spp., horseflies (Tabanus spp.), Tannia spp., Tetanops spp., Tipula spp.

[0062] From the class of the Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.

[0063] 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, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus volvulus), Ostertagia spp., 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, and Wuchereria bancrofti.

[0064] In addition, protozoa such as Eimeria can also be controlled.

[0065] From the order of the 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., and Triatoma spp.

[0066] From the order of the Homoptera, for example, Acyrthosipon spp., Acrogonia spp., Aeneolamia spp., Agonascena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Plum Short-tailed Aphid (Brachycaudus helichrysii), Brachycolus spp., Cabbage Aphid (Brevicoryne brassicae), Small Brown Rice Looper (Calligypona marginata), Carneocephala fulgida, Sugarcane Flour Horned Aphid (Ceratovacuna lanigera), Cercopidae, Ceroplastes spp., Strawberry Aphid (Chaetosiphon fragaefolii), Sugarcane Yellow Snow Shield Scale (Chionaspis tegalensis), Tea Green Leafhopper (Chlorita onukii), Walnut Black Spotted Aphid (Chromaphis juglandicola), Black Brown Round Shield Scale (Chrysomphalus ficus), Corn Leafhopper (Cicadulina mbila), Coccomytilu shalli, Soft Scale (Coccus spp.), Tea Currant 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., Scaphoides titanus, 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, and Zygina spp.

[0067] From the order of the Hymenoptera, for example, Athalia spp., Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

[0068] From the order of the Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber.

[0069] From the order of the Isoptera, for example, Acromyrmex spp., Atta spp., Cornitermes cumulans, Microtermes obesi, Odontotermes spp., Reticulitermes spp.

[0070] From the order of the Lepidoptera, for example, Acronicta major, Adoxophyes spp., Aedia leucomelas, Agrotis spp., Alabama spp., Amyelois transitella, Anarsia spp., Anticarsia spp., Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora., Capua reticulana, Carpocapsa pomonella), Carposina niponensis., Cheimatobia brumata, Chilo spp., Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp., Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias insulana, Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina), Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Etiella spp., Eulia spp., Eupocilia ambiguella, Euproctis spp., Euxoa spp.), Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., Hedylepta spp., Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., Lithocolletis spp., Lithophane antennata), Lobesia spp., Loxagrotis albicosta, Lymantria spp., Lyonetia spp., Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Mocis spp., Mythimna separata, Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp., Ostrinia spp., Oulema oryzae, Panolis flammea, Parnara spp., Pectinophora spp., Perileucoptera spp., Phthorimaea spp., Phyllocnistis citrella, Phyllonorycter spp., Pieris spp., Platynota stultana, Plusia spp., Plutella xylostella, Prays spp., Prodenia spp.), Protoparce spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Scirpophaga spp., Scotia segetum, 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.

[0071] From the order of the Orthoptera, for example, Acheta domesticus, Blatta orientalis, Blattella germanica, Dichroplus spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.

[0072] From the order of the Siphonaptera, for example, Ceratophyllus spp. and Xenopsylla cheopis.

[0073] From the order Symphyla, for example, Scutigerella spp.

[0074] From the order of the Thysanoptera, for example, Anaphothrips obscures, Baliothrips biformis, Drepanothris reuteri, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.

[0075] From the order of the Thysanura, for example, Lepisma saccharina.

[0076] 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.

[0077] If appropriate, the active compound combinations according to the invention can also be used, at certain concentrations or application rates, as herbicides, safeners, growth regulators or as agents for improving plant properties, or as microbicides, for example fungicides, mildewicides, bactericides, viricides (including agents against viroids) or as agents against MLOs (mycoplasma-like) and RLOs (rickettsia-like). If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds.

[0078] The invention also relates to formulations comprising at least one active compound according to the invention and to use forms prepared from these formulations as crop protection compositions and / or insecticides, for example drenches, drips and sprays, which optionally contain other crop protection agents and / or insecticides and / or activity-enhancing adjuvants, for example penetrants, for example vegetable oils (such as rapeseed oil, sunflower oil), mineral oils (such as paraffin oil), alkyl esters of vegetable fatty acids (such as rapeseed oil methyl ester or soybean oil methyl ester) or alkanol alkoxylates, and / or spreaders such as alkylsiloxanes and / or salts, for example organic or inorganic ammonium or phosphonium salts (such as ammonium sulfate or diammonium hydrogen phosphate), and / or retention promoters such as dioctyl sulfosuccinate or hydroxypropyl guar polymers, and / or wetting agents such as glycerol and / or fertilizers, for example fertilizers containing ammonium, potassium or phosphorus.

[0079] Conventional formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), oil-in-water emulsions (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS); these and other possible formulation types are described, for example, by Crop Life International in Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers-173 prepared by the FAO / WHO Joint Meeting on Pesticide Specification, 2004, ISBN: 9251048576. In addition to one or more active compounds according to the invention, the formulations optionally contain other agrochemically active compounds.

[0080] Preference is given to formulations or use forms which contain auxiliary agents (e.g., fillers, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners, and / or other auxiliary agents, such as adjuvants). Adjuvants in the context of the present invention are components which enhance the biological effect of the formulation without themselves having a biological effect. Examples of adjuvants are agents which promote retention, spreading, adhesion to leaf surfaces, or penetration.

[0081] These preparations are made in a known manner, for example by mixing the active compound with an auxiliary agent, such as a filler, a solvent and / or a solid carrier and / or other auxiliary agents such as a surfactant. These preparations are made in a suitable device or are prepared before or during use.

[0082] Substances used as auxiliaries are suitable for imparting specific properties, such as certain physical, technical and / or biological properties, to the active compound preparations and / or to the use forms prepared therefrom (eg ready-to-use crop protection compositions, such as spray liquors or seed dressings).

[0083] Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, such as aromatic and nonaromatic hydrocarbons (e.g. paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (if appropriate also substituted, etherified and / or esterified), 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).

[0084] If the extender used is water, organic solvents, for example, can also be used as auxiliary solvents. Suitable liquid solvents are, inter alia: aromatic compounds, such as xylene, toluene, or alkylnaphthalenes; chlorinated aromatic compounds and chlorinated aliphatic hydrocarbons, such as chlorobenzene, vinyl chloride, or methylene chloride; 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; highly polar solvents, such as dimethylformamide and dimethyl sulfoxide; and water.

[0085] In principle, all suitable solvents can be used, examples of suitable solvents being aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes, 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 ethers and esters thereof; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strongly polar solvents, such as dimethyl sulfoxide; and water.

[0086] In principle, all suitable carriers can be used. Useful carriers include, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, as well as ground synthetic minerals such as highly dispersed silica, aluminum oxide and natural and synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of the aforementioned carriers can also be used. Suitable solid carriers for granules are, for example, ground and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, synthetic particles of inorganic and organic powders, and particles of organic materials such as sawdust, paper, coconut shells, corn cobs and tobacco stalks.

[0087] Liquefied gaseous fillers or solvents may also be used. Particularly suitable fillers or carriers are those which are gaseous at room temperature and atmospheric pressure, such as aerosol propellant gases, for example halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide.

[0088] Examples of emulsifiers and / or foaming agents, dispersants or wetting agents with ionic or nonionic properties, or mixtures of these surfactants include polyacrylates, ligninsulfonates, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates 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 (for example alkyltaurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of compounds containing sulfates, sulfonates and phosphates, for example alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates, or protein hydrolysates, ligninsulfite waste liquors and methylcellulose. The presence of a surfactant is advantageous if one of the active compounds and / or one of the inert carriers is insoluble in water and application takes place in water.

[0089] Other auxiliaries that may be present in the formulations and in the use forms derived therefrom include dyes, for example 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 trace nutrients, such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts and zinc salts.

[0090] Other ingredients may be stabilizers, such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents that enhance chemical and / or physical stability. Foaming agents or defoamers may also be present.

[0091] As further adjuvants, the formulations and the use forms obtained therefrom may also contain viscosity-increasing agents, for example: carboxymethylcellulose; 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 cephalin and lecithin, as well as synthetic phospholipids. Other possible adjuvants are mineral oils and vegetable oils.

[0092] Optionally, other adjuvants may be present in the formulations and in the use forms derived therefrom. Examples of such additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic agents, penetrants, retention promoters, stabilizers, chelating agents, complexing agents, wetting agents, and spreading agents. In general, the active compound may be combined with any solid or liquid additive commonly used for formulation purposes.

[0093] Useful retention promoters include all those substances which reduce the dynamic surface tension, such as dioctyl sulfosuccinate, or which increase viscoelasticity, such as hydroxypropyl guar polymers.

[0094] In the context of the present invention, useful penetrants are all substances that are generally used to increase the penetration of agrochemical active compounds 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 epidermis and thus increase the mobility of the active compound in the epidermis. This property can be determined by the method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152). Examples include alkanol alkoxylates, such as coconut fatty acid ethoxylate (10) or isotridecyl ethoxylate (12); fatty acid esters, such as rapeseed oil methyl ester or soybean oil methyl ester; fatty amine alkoxylates, such as tallowamine ethoxylate (15); or ammonium and / or phosphonium salts, such as ammonium sulfate or diammonium hydrogen phosphate.

[0095] The formulation contains preferably 0.00000001 to 98% by weight of active ingredient or more preferably 0.01% to 95% by weight of active ingredient, more preferably 0.5% to 90% by weight of active ingredient, based on the weight of the formulation.

[0096] The active ingredient content of the use forms (crop protection compositions) obtained from the formulations can vary within wide ranges. The active ingredient concentration of the use forms can generally be from 0.00000001 to 95% by weight of active ingredient, preferably from 0.00001 to 1% by weight of active ingredient, based on the weight of the use form. Application is carried out in a conventional manner suitable for the use form.

[0097] The active compounds of the present invention can be used alone or in the form of formulations, including mixtures with one or more suitable fungicides, bactericides, acaricides, nematicides, insecticides, microbicides, fertilizers, attractants, sterilants, synergists, safeners, semiochemicals, and / or plant growth regulators, for purposes such as expanding the spectrum of activity, prolonging the duration of action, increasing the rate of action, preventing repulsion, or preventing the development of resistance. Furthermore, plant growth can be improved by combinations that improve tolerance to abiotic stress factors, such as increased tolerance to high or low temperatures, increased tolerance to drought, or salt content in water and / or soil. The quality of flowering and fruiting can also be improved, germination performance and root development can be optimized, harvesting can be made easier and yields can be increased, maturation can be accelerated, the quality and / or nutritional value of the harvested product can be improved, the shelf life of the harvested product can be extended, and / or its processing properties can be improved. In short, the combination of the active compounds of the present invention and the shared components produces a synergistic effect, i.e., the effectiveness of the mixture is greater than that of the individual components. The combinations are generally available in the form of premixes, tank mixes or ready mixes and can also be used for seed application.

[0098] Particularly advantageous co-components are, for example, those listed below.

[0099] Insecticides / Acaricides / Nematicides:

[0100] The active compounds indicated here by their common names are known and described, for example, in the Pesticide Manual (“The Pesticide Manual” 14th ed., British Crop Protection Council 2006) or can be found on the Internet (for example http: / / www.alanwood.net / pesticide).

[0101] (1) Acetylcholinesterase (AChE) inhibitors, such as carbamates, for example, alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, fenamiprid, formetanate), furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, and xylylcarb;

[0102] or organophosphates, for example, acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-methyl, eton-S-methyl), diazinon, dichlorvos (DDVP), dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenephos, nophos), imicyafos, isofenphos, O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, methyl parathion (parathion-methyl), phophorate henthoate), phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulphotep, tebupirimfos,Temephos, terbufos, tetrachlorvinphos, thiometon-methyl, triazophos, triclorfon, and vamidothion.

[0103] (2) GABA-controlled chloride channel antagonists, such as cyclopentadienyl organochlorides, for example, chlordane and endosulfan;

[0104] or phenylpyrazoles (fiprols), for example, ethiprole, fipronil.

[0105] (3) Sodium channel modulators / potential-dependent sodium channel blockers, for example, pyrethroids, e.g.Acrinathrin, allethrin, d-cis-transallethrin, d-trans allethrin), bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, cyfluthrin, β-cyfluthrin, cyhalothrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin thrin), cyphenothrin, deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(1R)-trans isomer], isomer]), prallethrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) isomer], tralomethrin, transfluthrin;

[0106] Or DDT; or methoxychlor.

[0107] (4) Nicotinic acetylcholine receptor (nAChR) agonists, such as neonicotinoids, for example, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; or nicotine.

[0108] (5) Nicotinic acetylcholine receptor (nAChR) allosteric activators, such as spinosyns, such as spinetoram and spinosad.

[0109] (6) Chloride channel activators, such as avermectins / milbemycins, for example, abamectin, emamectin-benzoate, lepimectin, milbemycin.

[0110] (7) Juvenile hormone mimetics, for example, juvenile hormone analogs, for example, hydroprene, kinoprene, methoprene; or fenoxycarb; or pyriproxifen.

[0111] (8) Active substances with unknown or non-specific mechanisms of action, such as halogenated alkanes, for example methyl bromide, other halogenated alkanes; or chloropicrin; or sulfuryl chloride; or borax; or tartar emetic.

[0112] (9) Selective antifeedants, for example, pymetrozine; or flonicamid.

[0113] (10) Mite growth inhibitors, for example, clofentezine, hexythiazox, diflovidazin; or etoxazole.

[0114] (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.

[0115] (12) Oxidative phosphorylation inhibitors, ATP disruptors, such as diafenthiuron; or organotin acaricides, such as azocyclotin, cyhexatin, fenbutatin-oxide; or propargite; or tetradifon.

[0116] (13) Oxidative phosphorylation uncouplers that act by interrupting the H proton gradient, e.g., chlorfenapyr, dinitrocresol (DNOC), sulfluramid.

[0117] (14) Nicotinic acetylcholine receptor channel blockers, for example, bensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.

[0118] (15) Chitin biosynthesis inhibitors, type 0, for example, bistrifluron, chlofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron.

[0119] (16) Chitin biosynthesis inhibitors, type 1, for example, buprofezin.

[0120] (17) Molting disruptors, dipteran insects, for example, cyromazine.

[0121] (18) Ecdysone receptor agonists, for example, chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.

[0122] (19) Octopamine agonists, such as amitraz.

[0123] (20) Complex III electron transfer inhibitors, for example, hydramethylnon, acequinocyl or fluacrypyrim.

[0124] (21) Complex I electron transfer inhibitors, for example, METI acaricides, for example, fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; or rotenone (Derris).

[0125] (22) Voltage-dependent sodium channel blockers, for example, indoxacarb or metaflumizone.

[0126] (23) Acetyl-CoA carboxylase inhibitors, for example, tetramic acids and their derivatives, for example, spirodiclofen, spiromesifen, spirotetramat.

[0127] (24) Complex IV electron transfer inhibitors, for example, phosphines, such as aluminum phosphide, calcium phosphide, phosphine, zinc phosphide; or cyanide.

[0128] (25) Complex II electron transfer inhibitors, for example, cyenopyrafen.

[0129] (28) Ryanodine receptor modulators, for example, diamides, such as chlorantraniliprole and flubendiamide.

[0130] Other active ingredients with unknown or undetermined mechanisms of action, for example, amidoflumet, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite, cyantraniliprole (cyazypyr), cyflumetofen, dicofol, diflubenzuron, chlorpyrifos, chloranil ... ovidazin), fluensulfone, flufenerim, flufiprole, fluopyram, fufenozide, imidoclothiz, iprodione, meperfluthrin, pyridalyl, pyrifluquinazon, tetramethylfluthrin, iodomethane; and strains based on Bacillus firmus (particularly CNCM I-1582 strain, such as VOTiVO TM , BioNem), or the following known active compounds:

[0131] 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- 2-[(2-(2-fluoroethyl)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), Flup yradifurone, 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 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)oxy-λ 4 -sulfanylidene}cyanamide (known from WO2007 / 149134) and its diastereomers {[(1R)-1-(6-chloropyridin-3-yl)ethyl](methyl)oxy-λ 4 -sulfanylidene}cyanamide (A) and {[(1S)-1-(6-chloropyridin-3-yl)ethyl](methyl)oxy-λ 4 -sulfanylidene}cyanamide (B) (known from WO 2007 / 149134) and sulfoxaflor and its diastereomers [(R)-methyl(oxy){(1R)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ 4 -sulfanylidene]cyanamide (A1) and [(S)-methyl (oxy) {(1S)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ 4-sulfanylidene]cyanamide (A2), known as diastereoisomer group A (known from WO2010 / 074747, WO2010 / 074751), [(R)-methyl(oxy){(1S)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ 4 -sulfanylidene]cyanamide (B1) and [(S)-methyl (oxy) {(1R)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ 4-sulfanylidene]cyanamide (B2), known as diastereoisomer group B (known from WO2010 / 074747, WO2010 / 074751), as well as 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azabispiro[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]-11-hydroxy-9-azabispiro[4.2.4.2]tetradec-11-en-10-one [(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]chromen-4-yl]methylcyclopropanecarboxylate (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'-piperidinyl]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO2003 / 106457), 3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO2009 / 049851), 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethylcarboxylate (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-registration 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-chloropyridine-4-yl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile -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-methoxyprop-2-yl)-3-isobutylphenyl]-N-isobutyryl-3,5-dimethyl-1H-pyrazole-4-carboxamide (known from WO2002 / 096882), 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylic acid methyl ester (known from WO2005 / 085216), 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylic acid methyl ester 2-[({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylic acid methyl ester (known from WO 2005 / 085216), 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylic acid methyl ester (known from WO 2005 / 085216), 2-[3,5-dibromo-2-({[3-bromo-1-(3- chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-diethylhydrazinecarboxylic acid methyl ester (known from WO 2005 / 085216), 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazinecarboxylic acid methyl ester (known from WO 2005 / 085216), (5RS,7RS; 5RS,7 SR)-1-(6-chloro-3-pyridylmethyl)-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)-1,2,3,5,6,7-hexahydro-7-methyl-8-nitro-5-propoxyimidazo[1,2-a]pyridine3-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)-1H-tetrazol-1-yl]methyl}-1H-pyrazole-5-carboxamide [5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide (known from WO 2010 / 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 WO 2010 / 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 WO 2010 / 069502), (1E)-N-[(6-chloropyridin-3-yl)methyl]-N′-cyano-N-(2,2-difluoroethyl)acetamidine (known from WO 2008 / 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), 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethyl-1-methylhydrazinecarboxylic acid methyl ester (known from WO2011 / 049233).

[0132] fungicides

[0133] (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) benzyltrichloroethane (113096-99-4), (1.7) benzotriazole (113096-99-4), (1.8) benzotriazole (113096-99-4), (1.9) benzotriazole (113096-99-4), (1.10) benzotriazole (113096-99-4), (1.11) benzotriazole (113096-99-4), (1.12) benzotriazole (113096-99-4), (1.13) benzotriazole (113096-99-4), (1.14) bromuconazole (116255-48-2), (1.15) cyproconazole (113096-99-4), (1.16) benzotriazole (113096-99-4), (1.17) benzotriazole (113096-99-4), (1.18) benzotriazole (113096-99-4), (1.19) benzotriazole (113096-99-4), (20) benzotriazole (113096-99-4), (21) benzotriazole (113096-99-4), (22) benzotriazole (113096-99-4), 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) quinacridone 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) fluconazole (85509-19-9), (1.28) flutriafol (76674-21-0), (1.29) fluconazole (112839-33-5), (1.30) fluconazole-cis (112839-32-4), (1.31) fluconazole (85509-19-9), (1.32) flutriafol (76674-21-0), (1.33) furconazole (112839-33-5), (1.34) furconazole-cis (112839-32-4), (1.35) hexaconazole (79983-71-4), (1.36) imazalil (60534-80-7), (1.37) fluconazole (85509-19-9), (1.38) fluconazole (85509-19-9), (1.39) fluconazole (85509-19-9), (1.40) fluconazole (85509-19-9), (1.41) fluconazole (85509-19-9), (1.42) flutri27) 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 (1.48) onazole)(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 (12 9586-32-9), (1.61) 1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylic acid methyl ester (110323-95-0), (1.62) N'-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methyliminocarboxamide, (1.63) N-ethyl-N-methyl-N'-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}iminocarboxamide, and (1.64) O-{1-[(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl}-1H-imidazole-1-thiocarbonate (111226-71-2).

[0134] (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-diameric racemates 1RS, 4SR, 9RS and trans-diameric racemates 1RS, 4SR, 9SR) (88165-58-1), (2.12) isopyrazam (trans-diameric racemate), (2.13) isopyrazam (isopyrazam) (2.14) isopyrazam, trans-diameric enantiomers 1S, 4R, 9R), (2.15) isopyrazam, cis-diameric racemates 1RS, 4SR, 9RS), (2.16) isopyrazam, cis-diameric enantiomers 1R, 4S, 9R), (2.17) isopyrazam, cis-diameric enantiomers 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-methoxypropane-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 (1 210070-84-0)(WO2010025451), (2.29) N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methylenenaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.30) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methylenenaphthalen-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-methylenenaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide.

[0135] (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) oxazolidinone (850881-70-8), (3.8) oxazolidinone (850881-70-8), (3.9) oxazolidinone (850881-70-8), (3.10) oxazolidinone (850881-70-8), (3.11) oxazolidinone (850881-70-8), (3.12) oxazolidinone (850881-70-8), (3.13) oxazolidinone (850881-70-8), (3.14) oxazolidinone (850881-70-8), (3.15) oxazolidinone (850881-70-8), (3.16) oxazolidinone (850881-70-8), (3.17) oxazolidinone (850881-70-8), (3.18) oxazolidinone (850881-70-8), (3.19) oxazolidinone (850881-70-8), (3.20) oxazolidinone (850318-97-0), ( 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 n)(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 / 05 8723), (3.17) pyraclostrobin (175013-18-0) (WO2004 / 058723), (3.18)pyrametostrobin (915410-70-7) (WO2004 / 058723), (3.19) pyra oxystrobin(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 / 05872 3), (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-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide (326896-28-0), (3.27) (2E)-2-{2-[({[(2E,3E)-4-(2,6-difluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}acetamide 1-[(1-[(trifluoromethyl)phenyl]ethylidene}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] (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).

[0136] (4) Mitosis 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 (660 63-05-6), (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).

[0137] (5) Compounds capable of acting at multiple sites: 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 cyclohexane (1338-02-9), (5.7) oxidizing Copper (1317-39-1), (5.8) Copper oxychloride (1332-40-7), (5.9) Copper (2+) sulfate (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 ( 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 acetate 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, for example 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).

[0138] (6) Compounds capable of inducing host defense: for example, (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).

[0139] (7) Inhibitors of amino acid and / or protein biosynthesis: for example, (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).

[0140] (8) ATP production inhibitors: for example (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).

[0141] (9) Cell wall synthesis inhibitors: for example (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 ( A)(37248-47-8) and (9.9) valifenalate (283159-94-4; 283159-90-0).

[0142] (10) Inhibitors of lipid and membrane synthesis: for example, (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).

[0143] (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 in WO2005042474).

[0144] (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) furaxyl (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).

[0145] (13) Signal transduction inhibitors: for example, (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).

[0146] (14) Uncouplers: for example (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).

[0147] (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 (1 80409-60-3), (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 methyl sulfate ( 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 mide)(106917-52-6), (15.23) flutianil(304900-25-2), (15.24) fosetyl-aluminium(39148-24-8), (15.25) fosetyl-calcium, (15.26) fosetyl-sodium(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 dimethy ldithiocarbamate)(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(p entachlorophenol) 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) pyrrolidone (1018-71-9)(EP-A1559320), (15.47)tebufloquin(376645-78-2), (15.48)tebufloquin(76280-91-6), (15.49)tolnifanide(304911-98-6), (15.50)pyraclostrobin(72459-58-6), (15.51)salicylate(70193-21-4), (15.52)cyanamide(84527-51-5), (15.53)(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-methylpropanoate (517875-34-2) (known in 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 (1 003319-79-6), (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,6 H)-tetraketone, (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-benzopyran-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-dihydro- isoquinolin-1-yl)quinoline (861647-85-0) (known in 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 in WO2009094442), (15.75) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine (1174376-25-0) (known in 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-phenylpropan-2-oic acid ethyl ester, (15.78) N'-(4-{[3-( N-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methyliminocarboxamide, (15.79) N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-oxy)phenyl]propionamide, (15.80) N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-oxy)phenyl]propionamide, (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-methyliminocarboxamide, (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.

[0148] (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)-1-methyl- 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 (from EP-A 1559320) known), (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.

[0149] All of the mixing agents listed in categories (1) to (16) can optionally form salts with suitable bases or acids, provided this is possible on the basis of their functional groups.

[0150] A mixture with other known active compounds, such as herbicides, fertilizers, growth regulators, safeners, semiochemicals, or with agents for improving the properties of plants is also possible.

[0151] When used as insecticides, the active compounds of the present invention may also be present in their commercially available formulations and in use forms prepared by mixing said formulations with synergists. Synergists are compounds that enhance the activity of the active compounds, without necessarily being active themselves.

[0152] When used as insecticides, the active compounds according to the invention are also present in their commercially available formulations and in the use forms prepared from these formulations as a mixture with inhibitors which reduce the degradation of the active compounds after application to the plant habitat, on the surface of plant parts or in plant tissues.

[0153] All plants and plant parts can be processed according to the present invention. In the present invention, the implication of plant should be understood as all plants and plant populations, such as needed and unwanted wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants that can be obtained by conventional breeding and optimization method or by biotechnology and genetic engineering method or by the combination of the aforementioned methods, including transgenic plants and including plant cultivars protected or not protected by plant breeders' rights (plant breeders' rights). Plant parts can be understood as meaning all above-ground and underground plant parts and plant organs, such as buds, leaves, flowers and roots, and examples include leaves, needles, stems, stems, flowers, fruiting bodies, fruits, seeds, roots, tubers and rhizomes. Described plant parts also include harvested material and asexual and sexual propagation products, such as cuttings, tubers, rhizomes, branches and seeds.

[0154] The treatment of plants and plant parts with the active compounds according to the invention is carried out directly or by subjecting the compounds to the environment, habitat or storage space by customary treatment methods, such as dipping, spraying, evaporation, misting, broadcasting, painting, injection and, in the case of propagation materials, in particular seeds, coating with one or more layers.

[0155] As mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or plant species and plant cultivars obtained by conventional biological breeding methods, such as hybridization or protoplast fusion, and their parts are treated. In another preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and their parts are treated. The terms "parts" or "parts of plants" or "plant parts" are as explained above.

[0156] More preferably, the plants treated according to the invention are plant cultivars that are respectively commercially available or used. Plant cultivars are understood to mean plants with novel properties ("traits") obtained by conventional breeding, mutagenesis or recombinant DNA techniques. These can be cultivars, biotypes or genotypes.

[0157] Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, nutrition), the treatment according to the invention may also result in superadditive ("synergistic") effects. This may lead to effects that exceed those normally expected, such as a reduction in the application rate of the compounds and compositions used according to the invention and / or a broadening of their spectrum of action and / or an increase in their activity, improved plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to salt contents in water or soil, improved flowering quality, easier harvesting, accelerated maturation, increased harvest yield, increased quality of the harvested product and / or improved nutritional value, improved storage properties and / or processing properties of the harvested product.

[0158] Preferred transgenic plants or plant cultivars to be treated according to the invention (i.e., those obtained by genetic engineering) include all plants that, during the genetic modification, have received genetic material that imparts particularly advantageous, useful properties ("traits") to the plant. Examples of such properties include 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, increased quality and / or nutritional value of the harvested product, improved storage properties and / or processing properties of the harvested product. Other examples of such properties that are particularly emphasized include improved resistance of the plant to animal and microbial pests, such as insects, mites, phytopathogenic fungi, bacteria and / or viruses, and increased tolerance of the plant to certain herbicidally active compounds. Examples of transgenic plants which 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, rapeseed and fruit plants (fruits such as apples, pears, citrus fruits and grapes), with particular emphasis on maize, soybeans, potatoes, cotton, tobacco and rapeseed. Particularly emphasized properties are the increased resistance of the plants to insects, arachnids, nematodes, slugs and snails by toxins formed in the plants, in particular by the genetic material of Bacillus thuringiensis (e.g. by the genes CryIA(a), CryIA(b), CryIA(c), CryIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and combinations thereof; hereinafter referred to as "Bt plants"). The properties that are particularly emphasized are the increased resistance of plants to fungi, bacteria and viruses by means of systemic acquired resistance (SAR), systemins, phytoalexins, elicitors and resistance genes and corresponding expressed proteins and toxins. The properties that are particularly emphasized are also the increased tolerance of plants to certain herbicidally active compounds such as imidazolinones, sulfonylureas, glyphosate or phosphinothricin (e.g. "PAT" genes). The genes that confer the desired properties can also be present in combination with one another in transgenic plants. An example of a "Bt plant" that may be mentioned is the commercially available Bt plant under the trade name YIELD (e.g. corn, cotton, soybeans), (such as corn), (such as corn), (cotton), (cotton) and Examples of herbicide-tolerant plants that may be mentioned are those sold under the trade name Roundup (glyphosate-tolerant, e.g. corn, cotton, soybeans), Liberty (with glufosinate tolerance, such as rapeseed), (with imidazolinone tolerance) and Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) that may be mentioned include the varieties of maize, cotton and soybean (for example maize) that are tolerant to sulfonylureas. Of course, the above description also applies to plant cultivars having the genetic traits or genetic traits to be developed, which will be developed and / or marketed in the future.

[0159] The plants described above can be treated according to the invention in a particularly advantageous manner with the compounds of the general formula (I) or the active compound mixtures according to the invention. The preferred ranges stated above for the active compounds or mixtures also apply to the treatment of the plants described. Particular emphasis is placed on the treatment of plants with the compounds or mixtures specifically proposed according to the invention.

[0160] The active compounds according to the invention are active not only against plant pests, hygiene pests and stored product pests, but also against parasites (ectoparasites and endoparasites) of animals in the veterinary field, such as hard ticks, soft ticks, scabies mites, spider mites, flies (biting and sucking), parasitic fly larvae, lice, hair lice, feather lice and fleas. Such parasites include:

[0161] From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

[0162] From the order of the Mallophagida, and the suborders of the Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. and Felicola spp.

[0163] From the order Diptera and the suborders Nematocerina and Brachycerina, for example, 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.

[0164] From the order of the Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

[0165] From the order of the Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp. and Panstrongylus spp.

[0166] From the order of the Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattela germanica and Supella spp.

[0167] Subclass Acaria or Acarina and orders Metastigmate and Mesostigmata, for example, 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.

[0168] From the orders Actinedida (Prostigmata) and Acaridida (Astigmata), for example, 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.

[0169] The active compound of formula (I) of the present invention is also suitable for controlling arthropods that attack the following animals: agricultural production livestock, such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese and bees, other pets, such as dogs, cats, caged birds and ornamental fish, and experimental animals, such as hamsters, guinea pigs, rats and mice. The control of such arthropods is intended to reduce mortality and yield (meat, milk, wool, hides, eggs, honey, etc.), thereby making animal husbandry more economical and simpler by using the active compound of the present invention.

[0170] The active compounds of the present invention are used in the veterinary field and animal husbandry in a known manner, and the forms of administration are: enteral administration by means of, for example, tablets, capsules, potions, drench pills, granules, ointments, pills, feed-through and suppositories; parenteral administration by, for example, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implantation; nasal administration; skin administration by, for example, immersion or bathing, spraying, pouring and dripping, washing and dusting, and with the help of molded products comprising the active compound, such as collars, ear tags, tail tags, limb bands, halters, markers, etc.

[0171] When used for livestock, poultry, domestic animals, etc., the active compound of formula (I) can be used directly as a preparation (e.g., powder, emulsion, flowable agent) comprising an amount of 1 to 80% by weight of the active compound or after being diluted 100 to 10,000 times, or can be used in the form of a chemical bath.

[0172] Furthermore, it has been found that the compounds according to the invention have a strong insecticidal action against insects which destroy industrial materials.

[0173] The following insects may be mentioned as examples by way of preference but not limitation:

[0174] Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec., Tryptodendron spec., Apate monachus), oak borer (Bostrychus capucins), brown borer (Heterobostrychus brunneus), spiny borer (Sinoxylon spec.), bamboo borer (Dinoderus minutus);

[0175] Insects of the order Dermapterans, for example, Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;

[0176] Termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, and Coptotermes formosanus;

[0177] bristletails, such as silverfish (Lepisma saccharina).

[0178] Industrial materials in the context of the present invention are understood to mean inanimate materials such as, preferably, plastics, adhesives, sizes, paper and board materials, leather, wood and processed wood products and coating compositions.

[0179] The ready-to-use compositions may optionally also contain other insecticides and, optionally, one or more fungicides.

[0180] Furthermore, the compounds according to the invention can be employed for protecting objects which come into contact with saltwater or brackish water, in particular hulls, screens, nets, buildings, moorings and signaling systems, against fouling.

[0181] Furthermore, the compounds according to the invention can be used alone or in combination with other active compounds as antifouling compositions.

[0182] The active compounds of the present invention are also suitable for controlling animal pests, in particular insects, arachnids, and mites found in enclosed spaces such as homes, factory floors, offices, and vehicle cabins, in the household, hygiene, and protection of stored products. They can be used alone or in combination with other active compounds and adjuvants in household insecticide products for controlling such pests. They are effective against sensitive and resistant species and all developmental stages. Such pests include:

[0183] From the order of the Scorpionidea, for example, the Mediterranean yellow scorpion (Buthus occitanus).

[0184] From the order of the Acarina, for example, Argas persicus, Argas reflexus, Bryobia spp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.

[0185] From the order Araneae, for example, Aviculariidae, Orb-weaving spiders.

[0186] From the order Opiliones, for example, Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, and Opiliones phalangium.

[0187] Isopoda, such as comb lice and pillbugs.

[0188] From the order of the Diplopoda, for example, Blaniulus guttulatus, Polydesmus spp.

[0189] Chilopoda, for example, Geophilus spp.

[0190] From the order of the Zygentoma, for example, Ctenolepisma spp., silverfish, Lepismodes inquilinus.

[0191] From the order of the Blattaria, for example, the Oriental cockroach, the German cockroach, the Asian cockroach (Blattella asahinai), the Madeira cockroach, the Panchlora spp., the Parcoblatta spp., the Australian cockroach (Periplaneta australasiae), the American cockroach, the Big Brown cockroach (Periplaneta brunnea), the Smoky cockroach (Periplaneta fuliginosa), the Brown-banded cockroach (Supella longipalpa).

[0192] The suborder Saltatoria, such as house crickets.

[0193] From the order of the Dermoptera, for example, Forficula auricularia.

[0194] From the order of the Isoptera, for example, Kalotermes spp., Reticulitermes spp.

[0195] From the order of the Psocoptera, for example, Lepinatus spp., Liposcelis spp.

[0196] From the order of the Coleoptera, for example, Latheticus spp., Latheticus spp., Latheticus spp., Necrobia spp., Araneae, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, and Stegobium paniceum.

[0197] Diptera, for example, Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Red-headed Blowfly, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulina spp., Stomoxys calcitrans, Crane mosquito.

[0198] From the order of the Lepidoptera, for example, Achroia grisella, Greater wax moth, Plodia interpunctella, Tinea cloacella, Tinea cloacella, Tinea tatarica.

[0199] From the order of the Siphonaptera, for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopus cheops.

[0200] From the order of the Hymenoptera, for example, Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, house ants, Paravespula spp., Tetramorium caespitum,

[0201] From the order of the Anoplura, for example, Pediculus humanus capitis (Head lice), Pediculus humanus corporis (Body lice), Pemphigus spp., Phylloera vastatrix, Phthirus pubis (Pubic lice).

[0202] From the order of the Heteroptera, for example, Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

[0203] In the field of household insecticides, they can be used alone or in combination with other suitable active compounds, such as phosphoric esters, carbamates, pyrethroids, neonicotinoids, growth regulators or active compounds from other known classes of insecticides.

[0204] They are used in the form of aerosols, pressure-free sprays such as pump and atomizer sprays, automatic misting systems, foggers, foams, gels, evaporation products with evaporator sheets made of cellulose or plastic, liquid evaporators, gel and film evaporators, propellant-driven evaporators, energy-free or passive evaporation systems, moth-trapping paper, moth-trapping bags or moth-trapping glue, as granules or powders for use in baits for throwing or in bait stations. DETAILED DESCRIPTION

[0205] The following examples are provided to illustrate the present invention and should not be considered to limit the present invention in any way. The scope of the rights claimed in the present invention is described in the claims.

[0206] Given the economical efficiency and diversity of the compounds, we have selected and synthesized a number of compounds. A selection of these compounds is listed in Table 1 below. The specific compound structures and corresponding compound information are shown in Table 1. The compounds in Table 1 are intended to better illustrate the present invention but are not intended to limit the present invention. Those skilled in the art should not interpret this as limiting the scope of the present invention to the following compounds.

[0207] Table 1 Compound structures and 1 H NMR data

[0208] Table A is constructed in the same manner as Table 1 above, except that the general formula I is replaced by the general formula I′ having a chiral center. (When n is 1 in Formula I), and in Table A, the entries under the "Serial Number" column heading are sequentially recited 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), and 126(R). For example, 16(R) corresponds to the compound in Table 1 wherein the S* position of compound 16 is in R configuration.

[0209] 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 commercially or can be prepared by methods known in the literature or as described in detail. It will be understood by those skilled in the art that other synthetic routes can also be used to synthesize the compounds of the present invention. Although the 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 these modifications or variations of the preparation methods of the present invention that result in various isomerizations of the compounds are included within the scope of the present invention. In addition, the preparation methods described below can be further modified according to the present disclosure using conventional chemical methods well known to those skilled in the art. For example, appropriate groups can be protected during the reaction, etc.

[0210] The following process examples are provided to facilitate a further understanding of the preparation methods of the present invention. The specific substances, types, and conditions used are intended to further illustrate the present invention and are not intended to limit its reasonable scope. The reagents used in the synthesis of the compounds in the table below are either commercially available or can be readily prepared by one of ordinary skill in the art.

[0211] Examples of representative compounds are shown below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0212] 1. Synthesis of Compound 7

[0213] Compound 7-1 (150 mg, 1 eq) was dissolved in 20 mL of solvent (dioxane: water = 10:1), and 7-2 (145 mg, 1.2 eq), potassium carbonate (205 mg, 3 eq) and 1,1'-bis(diphenylphosphino)ferrocenepalladium dichloride (II) dichloromethane complex (30 mg, 0.02 eq) were added in sequence. The mixture was protected by nitrogen and heated to 100 ° C. and stirred overnight. The reaction was completed by mid-control. The mixture was extracted with water and ethyl acetate three times, the organic phases were combined, dried, concentrated, and mixed, and purified by normal phase to obtain compound 7 (100 mg, yield 60%, white solid).

[0214] 2. Synthesis of Compound 14

[0215] (1) Compound 14-1 was added to a 100 ml eggplant-shaped flask, and DMF was added to dissolve it. 3.0 eq potassium dihydrogen phosphate, 3.0 eq potassium carbonate, 3.0 eq sodium dithionite and 2.0 eq compound 14-2 were added, and the temperature was raised to 40 degrees Celsius. The reaction was carried out for 2 hours. After filtration, the filtrate was extracted with water and ethyl acetate, and washed three times with saturated brine. The organic phase was dried and purified by normal phase column to obtain oily compound 14-3 (yield 65%).

[0216] (2) Compound 14-3, 3.0 eq potassium carbonate, 1.5 eq 7-2 and 0.05 eq [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride dichloromethane complex were dissolved in 30 ml of dioxane, 3 ml of water was added, nitrogen was replaced three times, the temperature was raised to 100 ° C and the reaction was allowed to proceed overnight. After the intermediate control reaction was completed, the sample was directly mixed and purified, and purified by normal phase column to obtain white solid compound 14 (yield 22%).

[0217] 3. Synthesis of Compound 16

[0218] Compound 7 (100 mg, 1 eq) was dissolved in dichloromethane, and m-chloroperbenzoic acid (47 mg, 0.8 eq) was added. The mixture was stirred at room temperature for 1 h. After the mid-control reaction was completed, the mixture was washed three times with saturated aqueous sodium bicarbonate solution. The organic phase was taken, dried, concentrated, mixed, and purified by normal phase to obtain compound 16 (100 mg, 77%, white solid).

[0219] 4. Synthesis of Compound 20

[0220] 150 mg of compound 7 was dissolved in dichloromethane, and m-chloroperbenzoic acid (10 eq) was added. The mixture was stirred at room temperature for 24 h. After the mid-control reaction was completed, the mixture was washed three times with saturated aqueous sodium bicarbonate solution. The organic phase was taken, dried, concentrated, mixed, and purified by normal phase to obtain compound 20 (120 mg, yield 73%, white solid).

[0221] 5. Synthesis of Compound 22

[0222] (1) 2.9 g of raw material 22-1 was dissolved in DMF, 2 equivalents of cyclopropyl bromide were added, and the reaction was carried out at room temperature for 2 hours. After the intermediate control reaction was completed, water was added to quench the reaction, EA was added, and the organic phase was washed with water twice and saturated brine twice, dried over anhydrous sodium sulfate, and then spin-dried to obtain a crude white solid 22-2 (3.1 g, 86% yield).

[0223] (2) Compound 22-2 (3.1 g, 1 eq) was dissolved in 50 mL of a mixed solution (concentrated HCl:EtOH = 1:5) in an oil bath and stirred at 60°C overnight. After the mid-control reaction was completed, the mixture was concentrated to give the crude product compound 22-3 (2.6 g, yield 99%).

[0224] (3) 300 mg of compound 22-3 was dissolved in 5 ml of acetonitrile, and 2 equivalents of copper bromide, 2 equivalents of cuprous bromide, and 2 equivalents of tert-butyl nitrite were added under ice bath. The mixture was reacted at room temperature for 2 h. After the reaction was completed, the solvent was dried by spin drying, and EA and water were added for extraction. The organic phases were combined and dried, and 400 mg of a crude product of brown liquid compound 22-4 was obtained by spin drying.

[0225] (4) 200 mg of compound 22-4 was dissolved in 5 ml of 1,4-dioxane and 0.5 ml of water, and 1 equivalent of 7-2, 0.03 equivalent of Pd(dppf)Cl2, and 3 equivalents of Cs2CO3 were added. Under nitrogen protection, the reaction was carried out at 100°C overnight. After the intermediate control reaction was completed, the sample was dried and purified by normal phase column to obtain compound 22 (150 mg, yield 67%) as a yellow oil.

[0226] 6. Synthesis of Compound 30

[0227] (1) 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 were added to a flask under nitrogen protection and reacted at 100°C overnight. After the reaction was completed, the reaction solution was directly used for the next reaction.

[0228] (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 22 ml of a mixed solvent of 1,4-dioxane:H2O=10:1 were directly added to the system. The reaction was carried out at 100°C under nitrogen protection overnight. After the reaction, the sample was directly mixed and purified to obtain 40 mg of compound 30 (total yield 22%).

[0229] 7. Synthesis of Compound 100

[0230] Compound 30-2 (200 mg, 0.57 mmol) was dissolved in a mixed solvent (1,4-dioxane 20 ml, H2O 2 mL) at room temperature, and compound 100-1 (156 mg, 0.68 mmol), potassium carbonate (235 mg, 1.71 mmol), and Pd(dppf)Cl2 (25 mg, 0.03 mmol) were added. The reaction solution was placed under nitrogen protection and reacted at 100°C for 4 h. The reaction was completed. The reaction solution was poured into water to quench the reaction and extracted three times with ethyl acetate. The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and purified by normal phase purification to obtain compound 100 (32 mg, 15% yield).

[0231] 8. Synthesis of Compound 104

[0232] Compound 14 (80 mg, 0.22 mmol) was dissolved in 20 ml of DCM. m-CPBA (50 mg, 0.24 mmol) was added under ice-cooling and stirred at room temperature for 2 h. The reaction was complete after central control. Water was added to the reaction solution, and the mixture was extracted three times with dichloromethane. The combined organic phases were washed three times with saturated sodium chloride solution, dried, and concentrated. Silica gel column chromatography afforded Compound 104 (70 mg, 84% yield) as a white solid.

[0233] Biological activity evaluation:

[0234] Dissolve the compound of the present invention in acetone and then dilute with water to form a gradient of different concentrations (ppm). Place peanut leaves in a petri dish and spray using a spray tower. After spraying, open the petri dish lid and allow it to completely dry at room temperature. Then, place 15 adult spider mites (Tetranychus truncatus), cinnabarinus (Tetranychus cinnabarinus), and two-spotted spider mites (Tetranychus urticae) in the dish. Each peanut leaf constitutes one replicate, and each treatment is repeated three times. Using water as a control, transfer the peanuts to a feeding environment after application. Check the number of dead insects after 48 hours, and calculate the mortality rate according to the formula: Mortality (%) = (number of dead insects / number of test insects) * 100.

[0235] Table 2 Representative acaricide test results

[0236] Note: N stands for no data; Reference compound A: Control compound B:

[0237] The compounds according to the invention have satisfactory insecticidal and / or acaricidal activity against animal pests, in particular when applied at relatively low application rates, and have high selectivity and improved compatibility in crops of useful plants.

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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