Benzoxazole derivatives as pesticidal compounds
Substituted bicyclic benzoxazole derivatives effectively address the need for broad-spectrum pest control by targeting invertebrate pests, providing high activity and favorable environmental and toxicological profiles.
Patent Information
- Application Number
- PCT/EP2025/073190
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-10-16
- Filing Date
- 2025-08-13
- Publication Date
- 2026-02-19
AI Technical Summary
There is a need for new compounds with high pesticidal activity against invertebrate pests like insects, arachnids, and nematodes that exhibit a broad activity spectrum, are environmentally friendly, and have a favorable toxicological profile, as existing agents face issues with pest resistance and limited efficacy.
Development of substituted bicyclic benzoxazole derivatives, including their stereoisomers, salts, and N-oxides, which are designed to target and control invertebrate pests effectively.
The compounds demonstrate high pesticidal activity against difficult-to-control pests, offering a broad spectrum of protection while being environmentally and toxicologically advantageous.
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Figure EP2025073190_19022026_PF_FP_ABST
Abstract
Description
[0001] 1 Benzoxazole derivatives as pesticidal compounds Description The invention relates to compounds of formula (I) or an agrochemically or verterinarily acceptable salt, stereoisomer, tautomer, or N-oxide thereof , wherein the variables are as defined below. The invention also relates to the use of compoundsof formula (I) as an agrochemical pesticide; to pesticidal compositions comprising a compound offormula (I) and another pesticidal ingredient; to a method for combating or controlling invertebrate pests, which method comprises contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound of the formula (I), the pesticidal mixture; to a method for protecting growing plants from attack or infestation byinvertebrate pests, which method comprises contacting a plant, or soil or water in which the plantis growing, with a pesticidally effective amount of at least one compound of the formula (I) or the pesticidal mixture; and to seeds comprising a compound of the formula (I) or the pesticidal composition in an amount of from 0.1 g to 10 kg per 100 kg of seeds; to a use of a compound of the formula (I) or of the pesticidal compositions, for protecting growing plants from attack orinfestation by invertebrate pests; and to a method for treating or protecting an animal frominfestation or infection by invertebrate pests which comprises bringing the animal in contact with a pesticidally effective amount of a compound of the formula (I). Invertebrate pests and in particular insects, arachnids and nematodes destroy growing andharvested crops and attack wooden dwelling and commercial structures, thereby causing largeeconomic loss to the food supply and to property. Accordingly, there is an ongoing need for new agents for combating invertebrate pests. WO2024085225 discloses the crystal structure of a bicyclic benzoxazole pyrimidinyl compound which has pesticidal activity. The invention differs from this compound in the nature of the residueR3. WO2023 / 036934, WO2021 / 053110 WO2021 / 053110, US 2022 / 0061325 Al,WO2014 / 125651, WO2013 / 018928 and WO 2014123205 disclose certain benzoxazole sulfone compounds with pesticidal activity. Due to the ability of target pests to develop resistance to pesticidally-active agents, there is an ongoing need to identify further compounds, which are suitable for combating invertebrate pests 2 such as insects, arachnids and nematodes. Furthermore, there is a need for new compounds having a high pesticidal activity and showing a broad activity spectrum against a large number of different invertebrate pests, especially against difficult to control insects, arachnids and nematodes. Furthermore, there is a need for compounds that are environmentally friendly anddisplay a favorable toxicological profile.It is therefore an object of the invention to identify and provide compounds, which exhibit a high pesticidal activity, have a broad activity spectrum against invertebrate pests, and show environmentally and toxicologically advantageous characteristics. It has been found that these objects can be achieved by substituted bicyclic compounds of formula(I), as depicted and defined below, including their stereoisomers, their salts, in particular theiragriculturally or veterinarily acceptable salts, their tautomers and their N-oxides. In a first aspect, the invention relates to a compound of formula (I), wherein R1 is S(O)m-C1-C4-alkyl, S(O)m-C3-C6-cycloalkyl, S(O)m-C3-C6-cycloalkyl-C1-C4-alkyl, whichare unsubstituted or halogenated; S(O)(=NH)RM, S(O)(=NRM)RM; C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, -O-C3-C6-cycloalkyl, all of which are unsubstituted, partially halogenated or fully halogenated; RWis C1-C4-alkyl, cyclopropyl, C3-C6-cycloalkyl-C1-C4-alkyl; mis 0, 1 or 2;n is 0, 1 or 2;R3is phenyl substituted with (a) one R4, or (b) substituted with one R4and one halogen, or (c) substituted with up to 5 halogens; or a six-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring system comprises one, two orthree, same or different heteroatoms O or N which may be unsubstituted or substituted with C1-C4-alkyl, and is substituted with (a) one R4, or (b) two halogens or (c) one R4and one halogen; or a 1,3-benzodioxole which is unsubstituted or halogenated; or C1-C4-alkynyl, which is unsubstituted or substituted with Si(R5)3; wherein R5is C1-C4- alkyl;R4is C(RM)2-(CN), CHRM-CN, C(RM)2-(CONH2), CHRM-(CONH2), C(RM)2-(CSNH2), CHRM- (CSNH2), 1-cyano-C3-C6-cycloalkyl, 1-C3-C6-cycloalkyl-carboxamide, 1-C3-C6- cycloalkyl-thiocarboxamide, O-CH2-CN, O-CHRM-CN, O-C(CN)(RM)2, O-C(CONH2)(RM)2, O-C(CSNH2)(RM)2, 3 O-1-cyano- C3-C6-cycloalkyl, O- C(CONH2)- C3-C6-cycloalkyl, O- C(CSNH2)- C3-C6- cycloalkyl; O-S(O)2-RM; C1-C3-alkoxy, which is unsubstituted or partially or fully halogenated; C3-C6-cycloalkyl- C1-C3-alkoxy which is unsubstituted or partially or fully halogenated, C3-C6-cycloalkoxywhich is unsubstituted or partially or fully halogenated; S(O)(=NRM)RM, S(O)(=NH)RM, N=S(O)(RM)2, CO-N=SO(RM)2, halogen, cyano, (=O), C(=O)H, C(=O)RM, difluoromethylen, each RM is independently C1-C3-alkyl which is unsubstituted or partially or fully halogenated;or C3-C6-cycloalkyl, or C3-C6-cycloalkyl in which at least one C is replaced by a heteroatom; or in case of two adjacent substituents RM, the substituents may form a ring together by a C2-C6-alkyl bridge, which is unsubstituted or partly or fully halogenated and in which one or more carbon atoms may be replaced by O or N;and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof, provided that if R1is S(O)(=NH)RMor S(O)(=NRM)RM, R3is not 5-chloro-pyrimidin-2-yl or 5- cyano-pyrimidin-2-yl. The compounds of the formula (I), and their agriculturally acceptable salts are highly active against animal pest, i.e. harmful arthropodes and nematodes, especially against insects and acaridae which are difficult to control by other means. Moreover, the invention relates to and includes the following embodiments:- compositions comprising at least one compound of formula (I) as defined above and a liquid orsolid carrier; - agricultural and veterinary compositions comprising an amount of at least one compound of formula (I) or an enantiomer, diasteromer or salt thereof as defined above; - methods for combating invertebrate pests, infestation, or infection by invertebrate pests, whichmethod comprises contacting said pest or its food supply, habitat or breeding grounds with apesticidally effective amount of at least one compound of formula (I) as defined above or a composition thereof; - methods for controlling invertebrate pests, infestation, or infection by invertebrate pests, which method comprises contacting said pest or its food supply, habitat or breeding grounds with apesticidally effective amount of at least one compound of formula (I) as defined above or acomposition comprising at least one compound of formula (I); - methods for preventing or protecting against invertebrate pests comprising contacting the invertebrate pests, or their food supply, habitat or breeding grounds with substituted imidazolium 4 compounds of the general formula (I) as defined above or a composition comprising at least one compound of formula (I) as defined above or a composition comprising at least one compound of formula (I); - methods for protecting crops, plants, plant propagation material and / or growing plants fromattack or infestation by invertebrate pests comprising contacting or treating the crops, plants, plantpropagation material and growing plants, or soil, material, surface, space, area or water in which the crops, plants, plant propagation material is stored or the plant is growing, with a pesticidally effective amount of at least one compound of formula (I) as defined above or a composition comprising at least one compound of formula (I);- non-therapeutic methods for treating animals infested or infected by parasites or preventinganimals of getting infected or infested by parasites or protecting animals against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of formula (I) as defined above or a composition comprising at least one compound of formula (I);- methods for treating, controlling, preventing or protecting animals against infestation or infectionby parasites by administering or applying orally, topically or parenterally to the animals a compound of the general formula (I) as defined above or a composition comprising at least one compound of formula (I); - seed comprising a compound of formula (I) as defined above, in an amount of from 0.1g to 10kgper 100kg of seed;- the use of the compounds of formula (I) as defined above for protecting growing plants or plant propagation material from attack or infestation by invertebrate pests; - the use of compounds of formula (I) or the enantiomers, diastereomers or veterinary acceptable salts thereof for combating parasites in and on animals;- a process for the preparation of a veterinary composition for treating, controlling, preventing orprotecting animals against infestation or infection by parasites which comprises adding a parasiticidally effective amount of a compound of formula (I) or the enantiomers, diastereomers and / or veterinary acceptable salt thereof to a carrier composition suitable for veterinary use; - the use of a compound of formula (I) or the enantiomers, diastereomers and / or veterinaryacceptable salt thereof for the preparation of a medicament for treating, controlling, preventing orprotecting animals against infestation or infection by parasites. All the compounds of formula (I) and, if applicable, their stereoisomers, their tautomers, their salts or their N-oxides as well as compositions thereof are particularly useful for controlling invertebrate pests, in particular for controlling arthropods and nematodes and especially insects.Therefore, the invention relates to the use of a compound of formula (I) as an agrochemicalpesticide, preferably for combating or controlling invertebrate pests, in particular invertebrate pests of the group of insects, arachnids or nematodes. 5 The term "compound(s) according to the invention" or "compound(s) of formula (I)" as used in the invention refers to and comprises the compound(s) as defined herein and / or stereoisomer(s), salt(s), tautomer(s) or N-oxide(s) thereof. The term "compound(s) of the invention" is to be understood as equivalent to the term "compound(s) according to the invention", therefore alsocomprising stereoisomer(s), salt(s), tautomer(s) or N-oxide(s) of compounds of formula (I). Asused herein, the term “compound(s) of the invention” or “compound(s) according to the invention” refers to the compound(s) of formula (I) as defined above, which are also referred to as “compound(s) of formula I” or “compound(s) I” or “formula I compound(s)”, and includes their salt(s), tautomer(s), stereoisomer(s), and N-oxide(s).The term "composition(s) according to the invention" or "composition(s) of the invention"encompasses composition(s) comprising at least one compound of formula (I) according to the invention as defined above, therefore also including a stereoisomer, an agriculturally or veterinary acceptable salt, tautomer or an N-oxide of the compounds of formula (I). The compounds of the invention may be amorphous or may exist in one or more differentcrystalline states (polymorphs) or modifications which may have a different macroscopicproperties such as stability or show different biological properties such as activities. The invention includes both amorphous and crystalline compounds of the formula (I), mixtures of different crystalline states or modifications of the respective compound I, as well as amorphous or crystalline salts thereof.The compounds of the formula (I) may have one or, depending on the substitution pattern, morecenters of chirality, in which case they are present as mixtures of enantiomers or diastereomers. The invention provides both the single pure enantiomers or pure diastereomers of the compounds of formula (I), and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula (I) or its mixtures. Suitable compounds of theformula (I) also include all possible geometrical stereoisomers (cis / trans isomers) and mixturesthereof. Cis / trans isomers may be present with respect to an alkene, carbon-nitrogen double- bond or amide group. The term "stereoisomer(s)" encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis / trans isomers). The invention relates to everypossible stereoisomer of the compounds of formula (I), i.e. to single enantiomers ordiastereomers, as well as to mixtures thereof. Depending on the substitution pattern, the compounds of the formula (I) may be present in the form of their tautomers. Hence the invention also relates to the tautomers of the formula (I) and the stereoisomers, salts, tautomers and N-oxides of said tautomers.Salts of the compounds of the formula (I) are preferably agriculturally and / or veterinary acceptablesalts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula (I) has a basic functionality or by reacting an acidic compound of formula (I) with a suitable base. 6 Suitable agriculturally or veterinary useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earthmetals, preferably calcium, magnesium, and barium, and of the transition metals, preferablymanganese, copper, zinc and iron, and also ammonium (NH4+) and substituted ammonium in which one to four of the hydrogen atoms are replaced by C1-C4-alkyl, C1-C4-hydroxyalkyl, C1-C4- alkoxy, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium,dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium,tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl- ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4- alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate,sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formulae I with an acid of the corresponding anion, preferably of hydrochloricacid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.The term “N-oxide” includes any compound of the invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety. The organic moieties groups mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix Cx-Cyindicates in each case the possible number of carbon atoms in the group. "Halogen" will be takento mean F, Cl, Br, and I, preferably F, Cl, Br. The terms compound(s) of formula (x) and compound(s) (x), wherein x is a roman or arab number are used herein interchangeably and refer to a single or several compounds as defined by the respective formula (x).The term “substituted with”, e.g. as used in "partially, or fully substituted with" means that one ormore, e.g.1, 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by one or more, same or different substituents as subsequently defined. Accordingly, for substituted cyclic moieties, e.g.1-cyanocyclopropyl, one or more of the hydrogen atoms of the cyclic moiety may be replaced by one or more, same or different substituents.The term "Cx-Cy-alkyl" as used herein (and also in Cx-Cy-alkylamino, di-Cx-Cy-alkylamino, Cx-Cy-alkylaminocarbonyl, di-(Cx-Cy-alkylamino)carbonyl, Cx-Cy-alkylthio, Cx-Cy-alkylsulfinyl and Cx-Cy- alkylsulfonyl) refers to a branched or unbranched saturated hydrocarbon group having n to m, e.g. 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, e.g. methyl, ethyl, propyl, 1- 7 methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2- methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-di- methylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers. C1-C4-alkyl means for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl. The term "Cx-Cy-haloalkyl" as used herein (and also in Cx-Cy-haloalkylsulfinyl and Cx-Cy-halo-alkylsulfonyl) refers to a straight-chain or branched alkyl group having n to m carbon atoms, e.g.1 to 10 in particular 1 to 6 carbon atoms (as mentioned above), where some or all of the hydro- gen atoms in these groups may be replaced by halogen atoms as mentioned above, e.g. C1-C4- haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and the like. The term C1-C10-haloalkyl in particular comprises C1-C2-fluoroalkyl, which is synonym with methyl or ethyl, wherein 1, 2, 3, 4 or 5 hydrogen atoms are substituted with fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoromethyl.Similarly, "Cx-Cy-alkoxy" and "Cx-Cy-alkylthio" (or Cx-Cy-alkylsulfenyl, respectively) refer to straight-chain or branched alkyl groups having n to m carbon atoms, e.g.1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as mentioned above) bonded through oxygen (or sulfur linkages, respectively) at any bond in the alkyl group. Examples include C1-C4-alkoxy such as methoxy,ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy, further C1-C4-alkylthio such as methylthio, ethylthio, propylthio, isopropylthio, and n-butylthio. Accordingly, the terms "Cx-Cy-haloalkoxy" and "Cx-Cy-haloalkylthio" (or Cx-Cy-haloalkylsulfenyl, resp.) refer to straight-chain or branched alkyl groups having n to m carbon atoms, e.g.1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as mentioned above) bonded through oxygen or sulfurlinkages, resp., at any bond in the alkyl group, where some or all of the hydrogen atoms in thesegroups may be replaced by halogen atoms as mentioned above, e.g. C1-C2-haloalkoxy, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoro- methoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy,2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoro-ethoxy, 2,2,2-trichloroethoxy and pentafluoroethoxy, further C1-C2-haloalkylthio, such as chloro- methylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoro- methylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoro- 8 methylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoro- ethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2- dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio and pentafluoroethylthio and the like. Similarly, the terms C1-C2-fluoroalkoxy and C1-C2-fluoroalkylthio refer to C1-C2-fluoroalkyl which is bound tothe remainder of the molecule via an oxygen atom or a sulfur atom, respectively.The suffix “-carbonyl” in a group or “C(=O)” denotes in each case that the group is bound to the remainder of the molecule via a carbonyl C=O group. This is the case e.g. in alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylcarbonylamino, and hydroxycarbonyl. For example, a hydroxycarbonylgroup would refer to a carbonic acid group -C(=O)OH, and an aminocyrbonyl group would referto an amide group -C(=O)NH2, both of which are bound to the remainder of the molecule via the carbonyl “C=O” group. The term "aryl" as used herein refers to a mono-, bi- or tricyclic aromatic hydrocarbon radical such as phenyl or naphthyl, in particular phenyl (also referred as to C6H5as subsitituent).The term "C3-Cy-cycloalkyl" as used herein refers to a monocyclic ring of 3- to y-memberedsaturated cycloaliphatic radicals, e.g. cyclopropyl (cC3H5), cyclobutyl (cC4H7), cyclopentyl (cC5H9), cyclohexyl (cC6H11), cycloheptyl, cyclooctyl and cyclodecyl. Accordingly, the term “C3-Cy-cycloalkoxy” as used herein refers to a “C3-Cy”-cycloalkyl moiety which is bonded to the rest of the molecule via an oxygen atom, such as in cyclopropoxy,cyclobutoxy, cyclopentoxy and cyclohexoxy.The term "cycloalkylalkyl" denotes as well as the term “alkyl which may be substituted with cycloalkyl” an alkyl group which is substituted with a cycloalkyl ring, wherein alkyl and cycloakyl are as herein defined. The term "C3-Cy-cycloalkenyl" as used herein refers to a monocyclic ring of 3- to y-memberedpartially unsaturated cycloaliphatic radicals.The term "cycloalkylcycloalkyl" denotes as well as the term “cycloalkyl which may be substituted with cycloalkyl” a cycloalkyl substitution on another cycloalkyl ring, wherein each cycloalkyl ring independently has from 3 to 7 carbon atom ring members and the cycloalkyls are linked through one single bond or have one common carbon atom. Examples of cycloalkylcycloalkyl includecyclopropylcyclopropyl (e.g. 1,1'-bicyclopropyl-2-yl), cyclohexylcyclohexyl wherein the two ringsare linked through one single common carbon atom (e.g. 1,1'-bicyclohexyl-2-yl), cyclohexylcyclopentyl wherein the two rings are linked through one single bond (e.g. 4- cyclopentylcyclohexyl) and their different stereoisomers such as (1R,2S)-1, 1'-bicyclopropyl-2-yl and (1R,2R)-1,1'-bicyclopropyl-2-yl.The term “carbocycle” or “carbocyclyl” includes, unlessotherwise indicated, in general a 3- to 12-membered, preferably a 3- to 8-membered or a 5- to 8-membered, more preferably a 5- or 6-membered mono-cyclic, ring comprising 3 to 12, preferably 3 to 8 or 5 to 8, more preferably 5 or 6 carbon atoms. The carbocyclic radicals may be saturated, partially unsaturated, or fully unsaturated. Preferably, 9 the term “carbocycle” covers cycloalkyl and cycloalkenyl groups as defined above, for example cyclopropane, cyclobutane, cyclopentane and cyclohexane rings. When it is referred to “fully unsaturated” carbocycles, this term also includes “aromatic” carbocycles. In certain preferred embodiments, a fully unsaturated carbocycle is an aromatic carbocycle as defined below,preferably a 6-membered aromatic carbocycle.The term "hetaryl" or “aromatic heterocycle” or “aromatic heterocyclic ring” includes monocyclic 5- or 6-membered heteroaromatic radicals comprising as ring members 1, 2, 3, or 4 heteroatoms selected from N, O, and S. Examples of 5- or 6-membered heteroaromatic radicals include pyridyl, i.e. 2-, 3-, or 4-pyridyl, pyrimidinyl, i.e. 2-, 4- or 5-pyrimidinyl, pyrazinyl, pyridazinyl, i.e. 3- or4-pyridazinyl, thienyl, i.e. 2- or 3-thienyl, furyl, i.e. 2-or 3-furyl, pyrrolyl, i.e. 2- or 3-pyrrolyl,oxazolyl, i.e.2-, 3- or 5-oxazolyl, isoxazolyl, i.e.3-, 4- or 5-isoxazolyl, thiazolyl, i.e.2-, 3- or 5- thiazolyl, isothiazolyl, i.e.3-, 4- or 5-isothiazolyl, pyrazolyl, i.e.1-, 3-, 4- or 5-pyrazolyl, i.e.1-, 2-, 4- or 5-imidazolyl, oxadiazolyl, e.g.2- or 5-[1,3,4]oxadiazolyl, 4- or 5-(1,2,3-oxadiazol)yl, 3- or 5- (1,2,4-oxadiazol)yl, 2- or 5-(1,3,4-thiadiazol)yl, thiadiazolyl, e.g.2- or 5-(1,3,4-thiadiazol)yl, 4- or5-(1,2,3-thiadiazol)yl, 3- or 5-(1,2,4-thiadiazol)yl, triazolyl, e.g. 1H-, 2H- or 3H-1,2,3-triazol-4-yl,2H-triazol-3-yl, 1H-, 2H-, or 4H-1,2,4-triazolyl and tetrazolyl, i.e.1H- or 2H-tetrazolyl. The terms “heterocycle”, "heterocyclyl" or “heterocyclic ring” includes, unless otherwise indicated, in general 3- to 12-membered, preferably 3- to 8-membered, 3- to 7-membered, or 5- to 8- membered, more preferably 5- or 6-membered, in particular 6-membered monocyclic heterocyclicradicals. The heterocyclic radicals may be saturated, partially unsaturated, or fully unsaturated.As used in this context, the term “fully unsaturated” also includes “aromatic”. In a preferred embodiment, a fully unsaturated heterocycle is thus an aromatic heterocycle, preferably a 5- or 6-membered aromatic heterocycle comprising one or more, e.g.1, 2, 3, or 4, preferably 1, 2, or 3 heteroatoms selected from N, O and S as ring members. Examples of aromatic heterocycles areprovided above in connection with the definition of “hetaryl”. Unless otherwise indicated, “hetaryls”are thus covered by the term “heterocycles”. The heterocyclic non-aromatic radicals usually comprise 1, 2, 3, 4 or 5, preferably 1, 2 or 3 heteroatoms selected from N, O, and S as ring members, where S-atoms as ring members may be present as S, SO or SO2, and N-atoms may be oxidized, or non-oxidized. Examples of 5- or 6-membered heterocyclic radicals comprisesaturated or unsaturated, non-aromatic heterocyclic rings, such as oxiranyl, oxetanyl, thietanyl,thietanyl-S-oxid (S-oxothietanyl), thietanyl-S-dioxid (S-dioxothiethanyl), pyrrolidinyl, pyrrolinyl, pyrazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1,3-dioxolanyl, thiolanyl, S-oxothiolanyl, S- dioxothiolanyl, dihydrothienyl, S-oxodihydrothienyl, S-dioxodihydrothienyl, oxazolidinyl, oxazolinyl, thiazolinyl, oxathiolanyl, piperidinyl, piperazinyl, pyranyl, dihydropyranyl,tetrahydropyranyl, 1,3- and 1,4-dioxanyl, thiopyranyl, S.oxothiopyranyl, S-dioxothiopyranyl,dihydrothiopyranyl, S-oxodihydrothiopyranyl, S-dioxodihydrothiopyranyl, tetrahydrothiopyranyl, S-oxotetrahydrothiopyranyl, S-dioxotetrahydrothiopyranyl, morpholinyl, thiomorpholinyl, S- oxothiomorpholinyl, S-dioxothiomorpholinyl, thiazinyl and the like. Examples for heterocyclic ring 10 also comprising 1 or 2 carbonyl groups as ring members comprise pyrrolidin-2-onyl, pyrrolidin- 2,5-dionyl, imidazolidin-2-onyl, oxazolidin-2-onyl, thiazolidin-2-onyl and the like. The terms “alkylene”, “alkenylene”, and “alkynylene” refer to alkyl, alkenyl, and alkynyl as defined above, respectively, which are bonded to the remainder of the molecule, via two atoms, preferablyvia two carbon atoms, of the respective group, so that they represent a linker between twomoieties of the molecule. In particular, the term “alkylene” may refer to alkyl chains such as CH2CH2, -CH(CH3)-, CH2CH2CH2, CH(CH3)CH2, CH2CH(CH3), CH2CH2CH2CH2, CH2CH2CH2CH2CH2, CH2CH2CH2CH2CH2CH2, and CH2CH2CH2CH2CH2CH2CH2.Similarly, “alkenylene” and “alkynylene” may refer to alkenyl and alkynyl chains, respectively.The term "5- to 6-membered carbocyclic ring" as used herein refers to cyclopentane andcyclohexane rings. Examples of 5- or 6-membered saturated heterocyclic rings include: 2-tetrahydrofuranyl, 3- tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-pyrazo- lidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-oxazolidinyl, 4-oxazo-lidinyl, 5-oxazolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 2-thiazolidinyl, 4-thia-zolidinyl, 5-thiazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1,2,4-oxadiazo- lidin-3-yl, 1,2,4-oxadiazolidin 5 yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazo- lidin-3-yl,-1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2-tetrahydro- pyranyl, 4-tetrahydropyranyl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 2-piperidinyl, 3-piperidinyl, 4-piperi-dinyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexa-hydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4- hexahydrotriazin-3-yl, 2-morpholinyl, 3-morpholinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 1- oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-2-yl, 1,1-dioxothio- morpholin-3-yl.Examples of 5- or 6-membered partially unsaturated heterocyclyl or heterocyclic rings include:2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien- 2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin- 3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin 3 yl, 2- isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3 dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl,2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2- , 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4-di- or 11 tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1,3,5-di- or tetrahydrotriazin-2-yl. Examples of 5- or 6-membered fully unsaturated heterocyclic (hetaryl) or heteroaromatic rings are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl,2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl,1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4- pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl. A "C2-Cy-alkylene" is divalent branched or preferably unbranched saturated aliphatic chain having 2 to m, e.g.2 to 7 carbon atoms, for example CH2CH2, -CH(CH3)-, CH2CH2CH2, CH(CH3)CH2,CH2CH(CH3), CH2CH2CH2CH2, CH2CH2CH2CH2CH2, CH2CH2CH2CH2CH2CH2, andCH2CH2CH2CH2CH2CH2CH2.The term “alkylamino” as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, more preferably 1 to 3 carbon atoms, which is bonded via a nitrogen atom, e.g. an –NH- group.The term “dialkylamino” as used herein refers to a straight-chain or branched saturated alkylgroup having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, more preferably 1 to 3 carbon atoms, which is bonded via a nitrogen atom, which is substituted by another straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, more preferably 1 to 3 carbon atoms, e.g. a methylamino or ethylamino group.The term "alkylthio "(alkylsulfanyl: alkyl-S-)" as used herein refers to a straight-chain or branchedsaturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (= C1-C4- alkylthio), more preferably 1 to 3 carbon atoms, which is attached via a sulfur atom. Examples include methylthio, ethylthio, propylthio, isopropylthio, and n-butylthio. The term "haloalkylthio" as used herein refers to an alkylthio group as mentioned above whereinthe hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and / or iodine.Examples include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1- fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethyl-thio and pentafluoroethylthio and the like. The term "alkylsulfinyl" (alkylsulfoxyl: C1-C6-alkyl-S(=O)-), as used herein refers to a straight-chain or branched saturated alkyl group (as mentioned above) having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (= C1-C4-alkylsulfinyl), more preferably 1 to 3 carbon atoms bonded throughthe sulfur atom of the sulfinyl group at any position in the alkyl group.The term "(halo)alkylsulfonyl" (alkyl-S(=O)2-) as used herein refers to a straight-chain or branched saturated (and halogenated) alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon 12 atoms (= C1-C4-(halo)alkylsulfonyl), preferably 1 to 3 carbon atoms, which is bonded via the sulfur atom of the sulfonyl group at any position in the (halo)alkyl group. The term "(halo)alkylsulfanyl" (alkyl-S-) as used herein refers to a straight-chain or branched saturated (and halogenated) alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbonatoms (= C1-C4-(halo)alkylsulfanyl), preferably 1 to 3 carbon atoms, which is bonded via the sulfuratom of the sulfanyl group at any position in the (halo)alkyl group. The term "(halo)alkylsulfinyl" (alkyl-S(=O)-) as used herein refers to a straight-chain or branched saturated (and halogenated) alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (= C1-C4-(halo)alkylsulfinyl), preferably 1 to 3 carbon atoms, which is bonded via the sulfuratom of the sulfinyl group at any position in the (halo)alkyl group.Accordingly, the terms (halo)alkylsulfanylalkyl, (halo)alkylsulfinylalkyl, and (halo)sulfonylalkyl as used for example in “C1-C4-alkylsulfanyl-C1-C4-alkyl”, “C1-C4-alkylsulfinyl-C1-C4-alkyl”, and “C1-C4- alkylsulfonyl-C1-C4-alkyl” relate to (halo)alkylsulfanyl-, (halo)alkylsulfinyl-, or (halo)alkylsulfonyl- groups that are bonded via the sulfur atom of the sulfanyl, the sulfinyl, or the sulfonyl group,respectively, to the alkyl group, which is in turn bonded to the rest of the molecule.The term "alkylcarbonyl" (C1-C6-C(=O)-) refers to a straight-chain or branched alkyl group as defined above, which is bonded via the carbon atom of a carbonyl group (C=O) to the remainder of the molecule. The term "alkoxycarbonyl" refers to an alkoxygroup group as defined above, which is bonded viathe carbon atom of a carbonyl group (C=O) to the remainder of the molecule.The term "alkylaminocarbonyl" (C1-C6-NH-C(=O)-) refers to a straight-chain or branched alkylamino group as defined above, which is bonded via the carbon atom of a carbonyl group (C=O) to the remainder of the molecule. Similarly, the term "dialkylaminocarbonyl" refers to a straight-chain or branched saturated alkyl group as defined above, which is bonded to a nitrogenatom, which is substituted with another straight-chain or branched saturated alkyl group asdefined above, which nitrogen atom in turn is bonded via a carbonyl group (C=O) to the remainder of the molecule. The term “S(O)(NRM)” refers to a group ,wherein RM is as defined for formula (I) and wherein the symbols and “§” mean the link tothe remainder of the molecule. The compounds of formula (I) can be prepared by standard methods of organic chemistry. If certain derivatives cannot be prepared by the processes outlined below, they can be obtained byderivatization of other compounds of formula (I) that are accessible by these methods. 13 Preparation methods that are generally useful for the preparation of compounds of formula (I) have been disclosed in WO2021 / 053110. Compounds of formula (II), corresponding to compounds of formula (I) may be prepared byreaction of compounds of formula (III) with compounds of formula (IV) as displayed under Process1: All variables in formulae (III), (IV), (V) and (II) have a meaning as defined for formula (I). Reactions of this type have been described in WO 2014123205.The intermediate (V) is prepared by reacting (III) and (IV) at temperatures in the range of 0 to120°C in an inert solvent in the presence of amide bond forming reagents such as such as DCC (dicyclohexyl-carbodiimide) and DIC (diisopropylcarbodiimide), benzotriazole derivatives, such as HATU (O-(7- azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate), HBTU ((Obenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate) and HCTU (1H-benzotriazolium-1-[bis(dimethylamino)methylene]-5-chloro tetrafluoroborate) and phosphonium-derived activators, such as BOP ((benzotriazol-1-yloxy)-tris(dimethylamino) phosphonium hexafluorophosphate), PyBOP ((benzotriazol-1-yloxy)-tripyrrolidinphosphonium hexafluorophosphate) and PyBrOP (bromotripyrrolidinphosphonium hexafluorophosphate). Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane, or petrolether; aromatic hydrocarbons, such as benzene, toluene, o-, m-, and p-xylene; halogenatedhydrocarbons, or halogenated aromatic C6-C10-hydrocarbons, such as CH2Cl2, CHCl3, CCl4, CH2ClCH2Cl, CCl3CH3, CHCl2CH2Cl, CCl2CCl2, or chlorobenzene; ethers, such as CH3CH2OCH2CH3, (CH3)2CHOCH(CH3)2, CH3OC(CH3)3(MTBE), CH3OCH3(DME), CH3OCH2CH2OCH3, CH3OC(CH3)2CH2CH3, dioxane, anisole, 2-methyltetrahydrofuran,tetrahydrofurane (THF), and diethylene glycol; nitriles, such as CH3CN, and CH3CH2CN; alcohols,such as CH3OH, CH3CH2OH, CH3CH2CH2OH, CH3CH(OH)CH3, CH3(CH2)3OH, and C(CH3)3OH, 14 CH2(OH)CH2(OH), and CH3CH(OH)CH2OH. Mixtures of the above solvents are also possible in presence of suitable bases such as pyrrolidine; tertiary amines, such as diisopropylethylamine, trimethylamine, triethylamine, triisopropylamine and N-methylpiperidine, imidazol, pyridine; substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and polycyclicamides and amidines, such as 1,8-diazabicycloundec-7-ene (DBU), 1,4-Diazabicyclo[2.2.2]octane (DABCO) etc. The compound of present invention (II) can be produced by intramolecular condensation of intermediate (V). The reaction is carried out in an organic solvent such as benzene, toluene, o-, m-, and p-xylene; halogenated hydrocarbons, or halogenated aromatic C6-C10-hydrocarbons, CH3CH2CH2OH, CH3CH(OH)CH3, CH3(CH2)3OH,and C(CH3)OH, CH2(OH)CH2(OH), and CH3CH(OH)CH2OH, o-, m-, and p-chloro benzene undermoisture free condition at an elevated temperature in the range of 50 to 200°C. In the reaction a condensing agent can be used as required from acetic anhydride, trifluoroacetic anhydride, EDCI hydrochloride, p-toluenesulfonic acid, acetic acid, and polyphosphoric acid. The compound of present invention (II) can also be produced in one step by reacting (III) and (IV) in presence ofcondesngin agent as described in previous process without isolating the intermediate (V) andfurther condensing directly to get the compound of present invention (II) as described above. Process 2: Compounds of formula (II), corresponding to compounds of formula (I) may be prepared byreaction of compounds of formula (III) with compounds of formula (VI) as displayed under Process2. All variables in formulae (III), (VI), (VII) and (II) have a meaning as defined for formula (I). Reactions of this type have been described in WO 2014132971. The intermediate (VII) is prepared by reacting (III) and (VI) at temperatures in the range of 0 to120OC in an inert solvent in the presence of bases such as pyrrolidine; tertiary amines, such asdiisopropylethylamine, trimethylamine, triethylamine, triisopropylamine and N-methylpiperidine, 15 imidazol, pyridine; substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and polycyclic amides and amidines, such as 1,8-diazabicycloundec-7-ene (DBU), 1,4- Diazabicyclo[2.2.2]octane (DABCO) etc. in suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane, or petrol ether; aromatic hydrocarbons, such as benzene,toluene, o-, m-, and p-xylene; halogenated hydrocarbons, or halogenated aromatic C6-C10-hydrocarbons, such as CH2Cl2, CHCl3, CCl4, CH2ClCH2Cl, CCl3CH3, CHCl2CH2Cl, CCl2CCl2, or chlorobenzene; ethers, such as CH3CH2OCH2CH3, (CH3)2CHOCH(CH3)2, CH3OC(CH3)3(MTBE), CH3OCH3(DME), CH3OCH2CH2OCH3, CH3OC(CH3)2CH2CH3, dioxane, anisole, 2- methyltetrahydrofuran, tetrahydrofurane (THF), and diethylene glycol; nitriles, such as CH3CN,and CH3CH2CN. The compound of present invention (II) can be produced by intramolecularcondensation of intermediate (VII). The reaction is carried out in an organic solvent such as benzene, toluene, o-, m-, and p-xylene; halogenated hydrocarbons, or halogenated aromatic C6- C10-hydrocarbons, CH3CH2CH2OH, CH3CH(OH)CH3, CH3(CH2)3OH, and C(CH3)3OH, CH2(OH)CH2(OH), and CH3CH(OH)CH2OH, o-, m-, and p-chloro benzene under moisture freecondition at an elevated temperature in the range of 50 to 200OC. In the reaction a condensingagent can be used as required from acetic anhydride, trifluoroacetic anhydride, EDCI hydrochloride, p-toluenesulfonic acid, acetic acid, and polyphosphoric acid. Process 3: Compounds of formula (II), corresponding to compounds of formula (I) may be prepared by reaction of compounds of formula (III) with compounds of formula (VIII) as displayed under Process 3. All variables in formulae (III), (VIII) and (II) have a meaning as defined for formula (I). Reactionsof this type have been described in WO 2014132971 and WO 2014123205. The reaction isusually carried out in suitable solvents such as in suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane, or petrol ether; aromatic hydrocarbons, such as benzene, toluene, o-, m-, and p-xylene; halogenated hydrocarbons, or halogenated aromatic C6-C10- hydrocarbons, such as CH2Cl2, CHCl3, CCl4, CH2ClCH2Cl, CCl3CH3, CHCl2CH2Cl, CCl2CCl2, orchlorobenzene; ethers, such as CH3CH2OCH2CH3, (CH3)2CHOCH(CH3)2, CH3OC(CH3)3 (MTBE),CH3OCH3(DME), CH3OCH2CH2OCH3, CH3OC(CH3)2CH2CH3, dioxane, anisole, 2- methyltetrahydrofuran, tetrahydrofuran (THF) at a temperature in the range of 0 to 120°C in presence of oxidizing agent such as oxygen, copper(II) chloride, copper (II) triflate, Zinc Oxide, 16 Iron Oxide, and DDQ as described in Journal of Molecular Structure (2024), 1312. The reaction can also be carried out in presence of acids such as acetic acid, trifluoroacetic acid, p- toluenesulfonic acid, and polyphosphoric acid. Also, the reaction can be carried out, in the presence of a sulfite, as necessary. Examples of the sulfite include sodium bisulfite and sodiumdisulfite.Process 4: Reaction of nitrile intermediate (IX) with III in presence of Lewis acids such as Copper (II) triflateas described in Journal of Chemical Research (2012), 36(6), 370-373, cesium hydroxide asdescribed in CN103304507, Sodium carbonate and Zinc (II) chloride as described in CN111349048 can also provide the desired product of interest (II). Process 5: 17 Intermediate (XII) can be produced by reacting intermediate (III) with acid intermediate (X) as described in process 1 or reaction between intermediate (III) and acid chloride (XI) as described in process 2. Further condensation reaction (as described in process 1 and 2) to get the keyintermediate (XIV) bearing key leaving group (LG) such as -F, -Cl, -Br, -I, -NO2, -OTf, -OTs, -OMs,etc. Similarly, reaction of intermediate (III) with XII as described in process 4 also provides the intermediate XIV. Intermediate (XV) can be obtained by the treatment of intermediate XII wherein LG can be Cl, Br, I, -OTf, or leaving group by displacement reaction nitro group (which can also be any other leavinggroup such as Cl, Br, I, F, -OTf, -OTs etc.) with HS-RW wherein RW is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, which groups are halogenated or non-halogenated is in presence of base e.g. potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride etc. in solvent like DMF, THF and DMSO at cooling to ambient temperature. Such method has been described in literature like Tetrahedron Letters, 2014, vol.55, # 22, p.3295 – 3298. Thisintermediate XIII can be further oxidized to achieve the final compound (II) by oxidation reactionof the corresponding sulfide intermediate, involving reagents such as, m-chloroperoxybenzoic acid, hydrogen peroxide, oxone, sodium periodate, sodium hypochlorite or tert-butyl hypochlorite and the solvents used for the oxidations include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water. Theamount of the oxidant to be used in the reaction is generally 1 to 3 moles, preferably 1 to 1.2moles, relative to 1 mole of the sulfide compounds VII to produce the sulfoxide compounds, and preferably 2 to 2.2 moles of oxidant, relative to 1 mole of the sulfide compounds XIII as described in WO 2015 / 091945 Al, WO 2016107742 and WO 2018095795. Furthermore, reaction of intermediate (XIV) directly with Sodium alkylsulfinate under heating condition in presence of baseas described in process 1 or without base at temperature ranging from 50-150°C gives desiredcompound of II.
[0002] 18 Process 6: Intermediate (XVIII) can be prepared by condensation of intermediate (XVI) with III as describedin process 3 and / or condensation of intermediate (XVII) with III as described in process 4.Furthermore, intermediate XIX can be prepared by the reaction as described in process 5. Also, further oxidation results in final compound II.
[0003] 19 Process 7: Intermediate XXIV can be obtained by the reaction of intermediate III with (XX) wherein X canbe Cl, Br, I, -OTf, or leaving group as described in process 1.Intermediate XXIV can be obtained by the reaction of intermediate III with (XXI) wherein X can be Cl, Br, I, -OTf, or leaving group as described in process 2. Intermediate XXIV can be obtained by the reaction of intermediate III with (XXII) wherein X can be Cl, Br, I, -OTf, or leaving group as described in process 3.Intermediate XXIV can be obtained by the reaction of intermediate III with (XXIII) wherein X canbe Cl, Br, I, -OTf, or leaving group as described in process 4. Furthermore, intermediate XXVI and XXV can be prepared form the intermediate (XXIV) as described in process 5. 20 Compounds of formula (II) can be prepared by reacting compound XXVI in which X is a leaving group such as, for example, chlorine, bromine or iodine (preferably bromine), or an aryl-, alkyl- or haloalkylsulfonate such as trifluoromethanesulfonate, with a reagent R3-B(OH)2 (XXVII), R3- B(OR2) (XXVIII) where R could be alkyl, aryl, cycloalkyl or pinacole type of cyclic groups of theformula, wherein R3 is as defined in formula I. The reaction may be catalyzed by a palladiumbased catalyst, involving for example bis(diphenylphosphino)ferrocene]dichloropalladium (II)(1:1) (Pd(dppf)Cl2). DCM complex, , tetrakis(triphenylphosphine)palladium(0) , bis(dibenzylideneacetone)palladium(O) (Pd(dba)2), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3; optionally in form of its chloroform adduct) or palladium(ll) acetate, and a ligand, forexample XantPhos ((5-diphenylphosphanyl-9,9-dimethyl-xanthen-4-yl)diphenylphosphane),RuPhos (2-dicyclohexylphosphino2',6'-diisopropoxybiphenyl), JohnPhos ([1,1 -biphenyl]-2- ylbis(1,1 -dimethyl-ethyl)phosphine), BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthalene), tol-BINAP ([2,2'-bis(di-p-tolyl-phosphino)- 1,1'- binaphthyl]) or tri-(o-tolyl)phosphine, in presence of a base, like sodium, potassium or cesium carbonate, or sodium or potassium tert-butylate, in asolvent or a solvent mixture, like, for example dioxane, 1,2-dimethoxyethane or toluene,preferably under inert atmosphere. The reaction temperature can preferentially range from room temperature to the boiling point of the reaction mixture, or the reaction may be performed under microwave irradiation. Such reactions have been described, for example, in Molecules 2012, 17, 4508-4521, Advanced Synthesis & Catalysis (2015), 357(2-3), 361-365, WO2022025242 A1,Org. Lett., 2001, 3, 2757-2759 or Synlett, 2009, 1761-1764. The reaction temperature canpreferentially range from room temperature to the boiling point of the reaction mixture, or the reaction may be performed under microwave irradiation. Such reactions have been described, for example, in Advanced Synthesis & Catalysis, 350(3), 391-394; 2008.
[0004] 21 Process 8a: 22 Process 8b Compounds of formula (XXIX) can be purchased commercially. Accordingly, compounds of formula (VI), (VI), (VIII), (XXXVI), (XXXV) wherein all variables have a definition as in formula (I),may for example be prepared as follows.Intermediate XXX can be obtained by the treatment of intermediate XXIX wherein X can be Cl, Br, I, -OTf, or leaving group by displacement reaction of nitro group (which can also be any other leaving group such as Cl,Br, I, F, -OTf, -OTs etc.) with HS-RW wherein RWis C1-C6-alkyl, C3-C6- cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, which groups are halogenated or non-halogenated is inpresence of base e.g. potassium carbonate, sodium carbonate, cesium carbonate, sodiumhydride etc. in solvent like DMF, THF and DMSO at cooling to ambient temperature. Such method has been described in literature like Tetrahedron Letters, 2014, vol. 55, # 22, p.3295 – 3298. Intermediate XXIX can be oxidized to SO (sulfoxide) and / or SO2 (sulfone), by oxidation reaction of the corresponding sulfide intermediate, involving reagents such as, m-chloroperoxybenzoicacid, hydrogen peroxide, oxone, sodium periodate, sodium hypochlorite or tert-butyl hypochloriteand the solvents used for the oxidations include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water. The amount of the oxidant to be used in the reaction is generally 1 to 3 moles, preferably 1 to 1.2 moles, relative to 1 mole of the sulfide compounds XXIX to produce the sulfoxide compounds,and preferably 2 to 2.2 moles of oxidant, relative to 1 mole of the sulfide compounds XXIX asdescribed in WO 2015 / 091945 Al, WO 2016107742 and WO 2018095795. Hydrolysis of compounds of formula (XXXI), as defined in formula I, and in which X is a leaving group, in particular those compounds wherein X is a halogen (even more preferably chlorine, bromine or 23 iodine), for example through heating (XXXI) in concentrated acid, such as concentrated hydrochloric acid HCI cone, or sulfuric acid H2SO4cone., preferably in the presence of water, optionally in the presence of an inert solvent, such as acetic acid or ethers (for example tetrahydrofuran, ethylene glycol dimethyl ether or 1,4-dioxane) gave XXXII. Such hydrolysisconditions, and variants thereof, are known to a skilled person. Suzuki coupling (as described inprocess 7) can be used to generate compound IV, which have a meaning as defined for formula (I), was reacted with compound III to generate (II) by direct condensation reaction or via intermediate by amide formation reaction followed by condensation reaction. Intermediate (IV) and (XXXII) can be further converted to corresponding acid chlorides (VI) and (XXXVI)respectively using thionyl chloride, oxalyl chloride, or the person with knowledge of chemistry canperform this organic transformation. These acid chloride intermediates can be further reacted with intermediate (III) to generate compound of formula (II) in one step by condensation reaction or by amide formation reaction as described in process 2. Similarly, first a Suzuki coupling reaction can be performed as described above to convert intermediate (XXIX) to the (XXXIII). Followed bysequence of SNAr displacement reaction to get the intermediate (XXXIV) as described above.Oxidation of (XXXIV) to (IX) using the oxidation protocol followed by acid hydrolysis to get the intermediate (IV). Intermediate (VII) and (XXXV) can be achieved by reduction reaction of nitrile intermediate (IX) and (XXXI) using DIBAL. These intermediates further reacted with (III) under oxidative reaction conditions to get the compound of formula (II). Process 9: The intermediate compound (XXXVIII) can either be purchased or produced by reacting the intermediate (XXXVII) under nitration reaction conditions. The reaction conditions includeconcentrated nitric acid in presence or absence of sulfuric acid, acetic acid. The reaction can alsobe carried out in presence of NaNO2, KNO2in concentrated sulfuric acid. The reaction is usually carried out in a solvent. such as dichloromethane and chloroform, acetic acid, concentrated sulfuric acid, concentrated nitric acid, water, and mixtures thereof. In the reaction, the nitrating agent is usually used in a ratio of 1 to 3 mol, based on 1 mol of the intermediate compound(XXXVII). The reaction temperature is usually within the range of -10 to 100°C. The reaction timeis usually within the range of 0.1 to 24 hours. The intermediate compound (III) can be produced by reacting the intermediate compound (XXXVIII) with hydrogen, in the presence of a hydrogenation catalyst condition. The transition metal compounds such as palladium carbon, palladium hydroxide, Raney nickel, and platinum 24 oxide can be used for the hydrogenation reaction in presence of Hydrogen. The reaction is usually carried out in THF, ethylene glycol dimethyl ether, tert-butyl methyl ether and 1, 4-dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, water, and mixtures thereof a in a hydrogen atmosphere of 1 to 100 atmospheric pressure. The reactiontemperature is usually within the range of -20 to 100°C. The reaction time is usually within therange of 0.1 to 24 hours. Accordingly, compounds of formula (XLIV), and (XLII), wherein all variables have a definition asin formula (I), may for example be prepared as follows. Compound (XXXIX) can either be purchased or synthesized as described in process 9. Reaction of (XXXIX) with corresponding 25 condensing partner as described in process 1 to 4 to provides intermediate (XL). Further oxidation of (XL) as described in process 5 at 0°C gives sulfoxide intermediate (XLI), which upon further coupling reaction as described in process 7 gives compound (XLII), where in all the variables have a definition as in formula (I). Similarly, complete oxidation of (XL) as described in process 5at 25 to 100°C gives sulfone intermediate (XLIII), which upon further coupling reaction asdescribed in process 7 gives compound (XLII), where in all the variables have a definition as in formula (I). Process 11: In another method, a compound of formula (XLVI) wherein all variables have a definition as in formula (I), may for example be prepared as follows. Intermediate (XXXIX) can be reacted with triethyl orthoformate, carbon monoxide, in presence of oxygen, zinc oxide, acids such as sulfuric acid, acetic acid at a temperature ranging from 25 to 150°C to generate intermediate (XLV).Furthermore, metal catalyzed C-H bond activation reaction coupling reactions to get thecompound (XLVI). The reaction may be catalyzed by a palladium based catalyst, involving for example bis(diphenylphosphino)ferrocene]dichloropalladium (II)(1:1) (Pd(dppf)Cl2). DCM complex, , tetrakis(triphenylphosphine)palladium(0) , bis(dibenzylideneacetone)palladium(O) (Pd(dba)2), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3; optionally in form of itschloroform adduct) or palladium(ll) acetate, and a ligand, for example XantPhos ((5-diphenylphosphanyl-9,9-dimethyl-xanthen-4-yl)diphenylphosphane), RuPhos (2- dicyclohexylphosphino2',6'-diisopropoxybiphenyl), JohnPhos ([1,1 -biphenyl]-2-ylbis(1,1 - dimethyl-ethyl)phosphine), BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthalene), tol-BINAP ([2,2'-bis(di-p-tolyl-phosphino)- 1,1'- binaphthyl]) or tri-(o-tolyl)phosphine, in presence of a base,like sodium, potassium or cesium carbonate, or sodium or potassium tert-butylate, in a solvent ora solvent mixture, like, for example dioxane, 1,2-dimethoxyethane or toluene, preferably under inert atmosphere. The reaction can also be performed using copper iodide, copper chloride, Dichlorobis(pyridine)nickel,1H-Imidazolium, 1,3-bis(2,4,6-trimethylphenyl)-, chloride (1:1). The reaction temperature can preferentially range from room temperature to the boiling point of thereaction mixture. Such reactions have been described in Chemistry - A European Journal (2023),29(44), e202301310, European Journal of Inorganic Chemistry (2023), 26(22), e202300126, ChemCatChem (2022), 14(24), e202201055, Science Bulletin (2022), 67(1), 71-78 etc. 26 The reaction mixtures are worked up in a customary manner, for example by mixing with water, separating the phases and, if appropriate, chromatographic purification of the crude products. Some of the intermediates and end products are obtained in the form of colourless or slightly brownish viscous oils which are purified or freed from volatile components under reducedpressure and at moderately elevated temperature. If the intermediates and end products areobtained as solids, purification can also be carried out by recrystallization or digestion. The N-oxides may be prepared from the inventive compounds according to conventional oxidation methods, e. g. by treating compounds I with an organic peracid such as metachloroperbenzoic acid (cf. WO 03 / 64572 or J. Med. Chem. 38(11), 1892-903, 1995); or with inorganic oxidizingagents such as hydrogen peroxide (cf. J. Heterocyc. Chem. 18(7), 1305-8, 1981) or oxone (cf. J.Am. Chem. Soc.123(25), 5962-5973, 2001). The oxidation may lead to pure mono-N-oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography. If the synthesis yields mixtures of isomers, a separation is generally not necessarily required sincein some cases the individual isomers can be interconverted during work-up for use or duringapplication (for example under the action of light, acids or bases). Such conversions may also take place after use, for example in the treatment of plants in the treated plant, or in the harmful fungus to be controlled. A skilled person will readily understand that the preferences for the variables defined herein, alsoin particular the ones given in the tables below for the respective substituents, given herein inconnection with compounds I apply for the intermediates (compounds II to XLVII) accordingly. Thereby, the substituents in each case have independently of each other or more preferably in combination the meanings as defined herein.The variables have, each on their own and in combination, the following preferred meanings.In a certain aspect, the invention relates to a compound of formula (I), wherein R1is S(O)m-C1-C4-alkyl, S(O)m-C3-C6-cycloalkyl, S(O)m-C3-C6-cycloalkyl-C1-C4-alkyl, which are unsubstituted or halogenated; S(O)(=NH)RM, S(O)(=NRM)RM,C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, -O-C3-C6-cycloalkyl, all of which are unsubstituted, partially halogenated or fully halogenated; RWis C1-C4-alkyl, cyclopropyl, C3-C6-cycloalkyl-C1-C4-alkyl; mis 0, 1 or 2; 27 nis 0, 1 or 2;R3is phenyl substituted with (a) one R4, or (b) substituted with one R4and one halogen, or (c) substituted with up to 5 halogens; or a six-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring system comprises one, two orthree, same or different heteroatoms O or N which may be unsubstituted or substituted with C1-C4-alkyl, and is substituted with (a) one R4, or (b) two halogens or (c) one R4and one halogen; or a 1,3-benzodioxole which is unsubstituted or halogenated; or C1-C4-alkynyl, which is unsubstituted or substituted with Si(R5)3; wherein R5is C1-C4- alkyl;R4is C(RM)2-(CN), CHRM-CN, C(RM)2-(CONH2), CHRM-(CONH2), C(RM)2-(CSNH2), CHRM- (CSNH2), 1-cyano-C3-C6-cycloalkyl, 1-C3-C6-cycloalkyl-carboxamide, 1-C3-C6- cycloalkyl-thiocarboxamide, O-CH2-CN, O-CHRM-CN, O-C(CN)(RM)2, O-C(CONH2)(RM)2, O-C(CSNH2)(RM)2, O-1-cyano- C3-C6-cycloalkyl, O- C(CONH2)- C3-C6-cycloalkyl, O- C(CSNH2)- C3-C6-cycloalkyl; O-S(O)2-RM; C1-C3-alkoxy, which is unsubstituted or partially or fully halogenated; C3-C6-cycloalkyl- C1-C3-alkoxy which is unsubstituted or partially or fully halogenated, C3-C6-cycloalkoxy which is unsubstituted or partially or fully halogenated;S(O)(=NRM)RM, S(O)(=NH)RM, N=S(O)(RM)2, CO-N=SO(RM)2, (=O), C(=O)H, C(=O)RM, difluoromethylen, each RMis independently C1-C3-alkyl which is unsubstituted or partially or fully halogenated; or C3-C6-cycloalkyl, or C3-C6-cycloalkyl in which at least one C is replaced by aheteroatom; or in case of two adjacent substituents RM, the substituents may form a ring together by a C2-C6-alkyl bridge, which is unsubstituted or partly or fully halogenated and in which one or more carbon atoms may be replaced by O or N;and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable saltsthereof, provided that if R1is S(O)(=NH)RMor S(O)(=NRM)RM, R3is not 5-chloro-pyrimidin-2-yl or 5-cyano-pyrimidin-2-yl. In one embodiment of the invention, R1is S(O)m-C1-C4-alkyl, S(O)m-C3-C6-cycloalkyl, S(O)m-C3-C6-cycloalkyl-C1-C4-alkyl, which are unsubstituted or halogenated, preferably halogenated.In another embodiment of the invention, R1is S(O)m-C1-C4-alkyl, which are halogenated. In still another embodiment, R1is S(O)m-C1-C4-alkyl, S(O)m-C3-C6-cycloalkyl, S(O)m-C3-C6-cycloalkyl-C1- C4-alkyl, which are unsubstituted or halogenated, preferably halogenated. 28 In another embodiment, R1is S(O)(=NH)RMor S(O)(=NRM)RM. In the embodiments of the invention, m is 0, 1 or 2, preferably 1.In another embodiment of the invention, R1 is (S=O)-CF3, SO2-CF3, SCF3, S(O)(=NH)CF3 orS(O)(=NCH3)CF3. In another embodiment of the invention, R1is (S=O)-CF3, SO2-CF3, SCF3. In another embodiment of the invention, R1is (S=O)-CF3. In another embodiment of the invention, R1is S(O)(=NH)RMor S(O)(=NRM)RM, wherein RMis each independently C1-C3-alkyl which is unsubstituted or partiallyor fully halogenated. In another embodiment of the invention, R1 is S(O)(=NH)CF3 orS(O)(=NCH3)CF3. In one embodiment of the invention, R1is C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, -O-C3-C6- cycloalkyl, all of which are unsubstituted, partially halogenated or fully halogenated.In one embodiment of the invention, RW is C1-C4-alkyl, cyclopropyl, C3-C6-cycloalkyl-C1-C4-alkyl,and n is 0, 1, or 2, preferably 2. In another embodiment of the invention, RWis C1-C4-alkyl and n is 0, 1, or 2, preferably 2. In another embodiment of the invention, RWis methyl, ethyl or isopropyl and n is 0, 1, or 2, preferably 2. In another embodiment of the invention, RWis ethyl and n is 2. In one embodiment of the invention, R1is (S=O)-CF3, SO2-CF3, SCF3, S(O)(=NH)CF3or S(O)(=NCH3)CF3, and RWis ethyl and n is 2. In one embodiment of the invention, R1is (S=O)-CF3, SO2-CF3, SCF3, and RWis ethyl, n is 2. In one embodiment of the invention, R1is S(O)(=NH)RMor S(O)(=NRM)RM, wherein RMis eachindependently C1-C3-alkyl which is unsubstituted or partially or fully halogenated, and RW is ethyl,n is 2. In another embodiment of the invention, R1is S(O)(=NH)CF3or S(O)(=NCH3)CF3, and RWis ethyl and n is 2. In one embodiment of the invention, R1is C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, -O-C3-C6- cycloalkyl, all of which are unsubstituted, partially halogenated or fully halogenated; and RWisethyl, n is 2.In one embodiment of the invention, R3is phenyl substituted with (a) one R4, or (b) substituted with one R4and one halogen, or (c) substituted with up to 5 halogens. In one embodiment of the invention, R3is phenyl substituted with one R4, or substituted with 2 or 3 halogens.In one embodiment of the invention, the compound of formula (I) is the compound I.A: 29 In one embodiment of the invention, R3is phenyl substituted with one R4and one fluoro atom. In one embodiment of the invention, the compound of formula (I) is the compound I.A-b: In one embodiment of the invention, the compound of formula (I) is the compound I.A’ or I.A’’ In one embodiment of the invention, R3is a six-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring systemcomprises one, two or three, same or different heteroatoms O or N which may be unsubstitutedor substituted with C1-C4-alkyl, and is substituted with one R4, or substituted with two halogens. In various embodiments, if R1is S(O)(=NH)RMor S(O)(=NRM)RM, R3is not 5-chloropyrimidin-2-yl or 5-cyanopyrimidin-2-yl. In various such embodiments, R3is not 5-chloropyrimidin-2-yl or 5-cyanopyrimidin-2-yl. In various embodiments, if R3 is pyrimidinyl and substituted with one R4, R4is not chloro or cyano. In another embodiment of the invention, the compound I is compound I*: whereinX is C, O;Y is C, N; 30 Zis C, N, O;M is C, N;A is C;wherein N is unsubstituted or substituted with C1-C4-alkyl, and one C atom is substituted with R4or two C atoms are substituted with halogen or one C atom is substituted with R4 and one Catom is substituted with halogen. In one embodiment of the invention, R3is a six-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring system isbound to the remainder of the molecule by a nitrogen atom (N-bound).In one embodiment of the invention, R3is one of the following heterocycles R3.1 to R3.5: In various embodiments, in these heterocycles, the R4in R3.7 is not chloro or cyano. In one embodiment of the invention, R3is one of the heterocycles R3.1 to R3.11.In one embodiment of the invention, R3 is one of the heterocycles R3.1 to R3.5.In one embodiment of the invention, R3is one of the heterocycles R3.4 or R3.5. In one embodiment of the invention, R3is one of the pyrimidines R3.7 to R3.11. In one embodiment of the invention, R3is R3.1, R3.2 or R3.3, preferably R3.1 or R.3.2. In one embodiment, R3is one of the heterocycles R3.1 to R3.6 and R3.8 to R3.11.In one embodiment of the invention, R3 is a 1,3-benzodioxole which is unsubstituted orhalogenated. In one embodiment of the invention, R3is C1-C4-alkynyl, which is unsubstituted or substituted with Si(R5)3; wherein R5is C1-C4-alkyl. In a particular embodiment, R3is propargyl which is 31 unsubstituted or substituted with Si(R5)3; wherein R5is C1-C4-alkyl. In a particular embodiment, R3is propargyl which is unsubstituted or substituted with SiMe3. These compounds are useful as intermediates for preparing other compounds of the present invention, but also have pesticidal activity of their own, thus they are also useful as pesticides. In various embodiments, R3is phenyl or a six-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring system comprises one, two or three, same or different heteroatoms O or N which may be unsubstituted or substituted with C1-C4-alkyl, wherein the phenyl or heterocyclic ring or ring system is substitutedwith one R4, wherein R4 is O-S(O)2-RM, C(RM)2-(CN), 1-cyano-C3-C6-cycloalkyl, O-CH2-CN, O-CHRM-CN, O-C(CN)(RM)2, O-C(CONH2)(RM)2, N=S(O)(RM)2, halogen, cyano; or a 1,3- benzodioxole which is unsubstituted or halogenated. These compounds are useful as intermediates for preparing other compounds of the present invention, but also have pesticidal activity of their own, thus they are also useful as pesticides. In the compounds of the present invention, halogen is preferably fluoro, chloro, bromine, more preferably fluoro or chloro, more preferably fluoro. In one embodiment of the invention, R4is C(RM)2-(CN), CHRM-CN, C(RM)2-(CONH2), CHRM-(CONH2), C(RM)2-(CSNH2), CHRM-(CSNH2), 1-cyano-C3-C6-cycloalkyl, 1-C3-C6-cycloalkyl-carboxamide, 1-C3-C6-cycloalkyl-thiocarboxamide, O-CH2-CN, O-CHRM-CN, O-C(CN)(RM)2, O- C(CONH2)(RM)2, O-C(CSNH2)(RM)2, O-1-cyano- C3-C6-cycloalkyl, O- C(CONH2)- C3-C6- cycloalkyl, O- C(CSNH2)- C3-C6-cycloalkyl; O-S(O)2-RM; C1-C3-alkoxy, which is unsubstituted or partially or fully halogenated; C3-C6-cycloalkyl-C1-C3-alkoxy which is unsubstituted or partially orfully halogenated, C3-C6-cycloalkoxy which is unsubstituted or partially or fully halogenated;S(O)(=NRM)RM, S(O)(=NH)RM, N=S(O)(RM)2, CO-N=SO(RM)2, halogen, cyano, (=O), C(=O)H, C(=O)RM, difluoromethylen. In one embodiment of the invention, R4is C(RM)2-(CN), CHRM-CN, C(RM)2-(CONH2), CHRM-(CONH2), C(RM)2-(CSNH2), CHRM-(CSNH2), 1-cyano-C3-C6-cycloalkyl, 1-C3-C6-cycloalkyl-carboxamide, 1-C3-C6-cycloalkyl-thiocarboxamide, O-CH2-CN, O-CHRM-CN, O-C(CN)(RM)2, O- C(CONH2)(RM)2, O-C(CSNH2)(RM)2, O-1-cyano- C3-C6-cycloalkyl, O- C(CONH2)- C3-C6- cycloalkyl, O- C(CSNH2)- C3-C6-cycloalkyl; O-S(O)2-RM; C1-C3-alkoxy, which is unsubstituted or partially or fully halogenated; C3-C6-cycloalkyl-C1-C3-alkoxy which is unsubstituted or partially orfully halogenated, C3-C6-cycloalkoxy which is unsubstituted or partially or fully halogenated;S(O)(=NRM)RM, S(O)(=NH)RM, N=S(O)(RM)2, CO-N=SO(RM)2, cyano, (=O), C(=O)H, C(=O)RM, difluoromethylen. 32 In one embodiment of the invention, R4is C(RM)2-(CN), CHRM-CN, C(RM)2-(CONH2), CHRM- (CONH2), C(RM)2-(CSNH2), CHRM-(CSNH2), 1-cyano-C3-C6-cycloalkyl, 1-C3-C6-cycloalkyl- carboxamide, 1-C3-C6-cycloalkyl-thiocarboxamide, O-CH2-CN, O-CHRM-CN, O-C(CN)(RM)2, O-C(CONH2)(RM)2, O-C(CSNH2)(RM)2, O-S(O)2-RM; C1-C3-alkoxy, which groups are unsubstitutedor partially or fully halogenated; C3-C6-cycloalkyl-C1-C3-alkoxy, S(O)(=NRM)RM, S(O)(=NH)RM, N=S(O)(RM)2, CO-N=SO(RM)2, halogen, cyano, (=O), C(=O)H, C(=O)RM, difluoromethylen. It is understood that if R4is (=O), i.e. oxo, two valencies of the substituted ring atom are used. Ifthe ring atom is a carbon atom, this means that R4 can only be oxo, if the ring is not fullyunsaturated. In one embodiment of the invention, each RMis independently C1-C3-alkyl which is unsubstituted or partially or fully halogenated; or C3-C6-cycloalkyl, or C3-C6-cycloalkyl in which at least one C isreplaced by a heteroatom; or in case of two adjacent substituents RM, the substituents may forma ring together by a C2-C6-alkyl bridge, which is unsubstituted or partly or fully halogenated and in which one or more carbon atoms may be replaced by O or N. In a particular embodiment of the invention, each RMis independently methyl, trifluoromethyl or cyclopropyl.In another particular embodiment of the invention, two adjacent substituents RM form a ringtogether by a C2-C6-alkyl bridge, which is unsubstituted or partly or fully halogenated and in which one or more carbon atoms may be replaced by O or N. Examples for such bridge substituents are shown as RM-b1 to RM-b8, without limiting to these structures: In a particular embodiment of the case of two adjacent substituents RM forming a bridge ring,RM-b1 may be the bridge. In one embodiment of the invention, R4is C(RM)2-(CN), CHRM-CN, C(RM)2-(CONH2), CHRM- (CONH2), C(RM)2-(CSNH2), CHRM-(CSNH2), 1-cyano-C3-C6-cycloalkyl, 1-C3-C6-cycloalkyl-carboxamide, 1-C3-C6-cycloalkyl-thiocarboxamide. In a particular embodiment, R4 is C(RM)2-(CN),C(RM)2-(CONH2), 1-cyano-C3-C6-cycloalkyl, or 1-C3-C6-cycloalkyl-carboxamide. In a particular embodiment, R4is C(CH3)2-(CN), C(CH3)2-(CONH2), 1-cyano-cyclopropyl, or 1-cyclopropyl- carboxamide. 33 In another embodiment of the invention, R4is O-CH2-CN, O-CHRM-CN, O-C(CN)(RM)2, O- C(CONH2)(RM)2, O-C(CSNH2)(RM)2, O-1-cyano- C3-C6-cycloalkyl, O- C(CONH2)- C3-C6-cycloalkyl or O- C(CSNH2)- C3-C6-cycloalkyl. In a particular embodiment, R4is O-C(CN)(RM)2, O- C(CONH2)(RM)2, or O-S(O)2-RM. In a particular embodiment, R4is O-C(CN)(CH3)2, or O-C(CONH2)(CH3)2. In a particular embodiment, R4 is O-S(O)2-RM, preferably O-S(O)2-CH3 or O-S(O)2-ethyl, or O-S(O)2-propyl, such as O-S(O)2-isopropyl or O-S(O)2-n-propyl, or O-S(O)2-butyl, or O-S(O)2-cycloalkyl, such as O-S(O)2-cyclopropyl, O-S(O)2-cyclobutyl, O-S(O)2-cyclopentyl, or O-S(O)2-cyclohexyl, or O-S(O)2-heterocyclyl, wherein the alkyl groups may be unsubstituted or partially or fully halogenated, in particular fluorinated. In another embodiment of the invention, R4is C1-C3-alkoxy, which is unsubstituted or partially or fully halogenated, or C3-C6-cycloalkyl-C1-C3-alkoxy which is unsubstituted or partially or fully halogenated, C3-C6-cycloalkoxy which is unsubstituted or partially or fully halogenated. In one embodiment, R4is C1-C3-alkoxy, which is fully halogenated, preferably trifluoromethoxy.In another embodiment of the invention, R4 is S(O)(=NRM)RM, S(O)(=NH)RM, N=S(O)(RM)2, or CO-N=SO(RM)2. In a particular embodiment, R4is S(O)(=NCH3)CH3S(O)(=NH)CH3, or N=S(O)(CH3)2. In another embodiment of the invention, R4is (=O), C(=O)H, C(=O)RM, difluoromethylen. In another embodiment of the invention, R4is halogen, preferably fluoro or chloro, preferably fluoro.In another embodiment of the invention, R4 is cyano.In some embodiments of the invention where R3is a heterocyclic ring or ring system, R4is oxo (=O). In such embodiments, R3may additionally comprise a halogen substituent.In another embodiment of the invention, R4 is C(RM)2-(CN), C(RM)2-(CONH2), 1-cyano-C3-C6-cycloalkyl, 1-C3-C6-cycloalkyl-carboxamide, O-C(CN)(RM)2, O-C(CONH2)(RM)2, O-S(O)2-RM; C1-C3-alkoxy, which is fully halogenated; S(O)(=NRM)RM, S(O)(=NH)RM, N=S(O)(RM)2, halogen, cyano, (=O), C(=O)H, C(=O)RM, difluoromethylen. In another embodiment of the invention, R4is C(CH3)2-(CN), C(CH3)2-(CONH2), 1-cyano-cyclopropyl, 1-cyclopropyl-carboxamide, O-C(CN)(CH3)2, O-C(CONH2)(CH3)2, O-S(O)2-CH3;C1-C3-alkoxy, which is fully halogenated (preferably trifluoromethoxy), S(O)(=NCH3)CH3S(O)(=NH)CH3, N=S(O)(CH3)2, halogen, cyano. The above definitions of R4apply to R3being phenyl and heterocyclyl. All the above options of R4may be combined with a halogen substituent on R3, such as fluoro, chloro or bromo.As used herein, the term “compound(s) of the invention” or “compound(s) according to the invention” refers to the compound(s) of formula (I) as defined above, which are also referred to 34 as “compound(s) of formula I” or “compound(s) I” or “formula I compound(s)”, and includes their salts, tautomers, stereoisomers, and N-oxides. MixturesThe invention also relates to a mixture of at least one compound of the invention with at least onemixing partner. Preferred are binary mixtures of one compound of the invention as component I with one mixing partner herein as component II. Preferred weight ratios for such binary mixtures are from 5000:1 to 1:5000, preferably from 1000:1 to 1:1000, more preferably from 100:1 to 1:100, particularly from 10:1 to 1:10. In such binary mixtures, components I and II may be used in equalamounts, or an excess of component I, or an excess of component II may be used.Mixing partners can be selected from pesticides, in particular insecticides, nematicides, acaricides, fungicides, herbicides, plant growth regulators and fertilizers. Preferred mixing partners are insecticides, nematicides, and fungicides. The following list M of pesticides, grouped according to the Mode of Action Classification of theInsecticide Resistance Action Committee (IRAC), together with which the compounds of theinvention can be used and with which potential synergistic effects might be produced, illustrates the possible combinations: M.1 AChE inhibitors: aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate,furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur,thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate; acephate, azamethiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifosmethyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos,isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos,pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos,thiometon, triazophos, trichlorfon, vamidothion; M.2. GABA-gated chloride channel antagonists: cyclodiene organochlorine compounds: endosulfan, chlordane; phenylpyrazoles: ethiprole, fipronil, flufiprole, pyrafluprole, pyriprole; M.3 Sodium channel modulators: pyrethroids: acrinathrin, allethrin, d-cis-trans allethrin, d-transallethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio-resmethrin,cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, 35 flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin,metofluthrin, momfluorothrin, epsilon-momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, transfluthrin; sodium channel modulators, e.g.:DDT, methoxychlor;M.4 nAChR agonists: neonicotinoids: acetamiprid, clothianidin, cycloxaprid, dinotefuran, im- idacloprid, nitenpyram, thiacloprid, thiamethoxam; 4,5-dihydro-N-nitro-1-(2-oxiranylmethyl)-1H- imidazol-2-amine, (2E-)-1-[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarbox- imidamide; 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydro-imidazo[1,2-a]pyridine; nicotine; sulfoxaflor; flupyradifurone; triflumezopyrim, fenmezoditiaz,flupyrimin, 1-[(2-chlorothiazol-5-yl)methyl]-3-(3,5-dimethylisoxazol-4-yl)pyrido[1,2-a]pyrimidine- 2,4-dione; M.5 Nicotinic acetylcholine receptor allosteric activators:spinosyns, e.g. spinosad or spineto-ram; M.6 Chloride channel activators from the class of avermectins and milbemycins, e.g. abamectin,emamectin benzoate, ivermectin, lepimectin, or milbemectin;M.7 Juvenile hormone mimics, such as hydroprene, kino-prene, methoprene; fenoxycarb, or pyriproxyfen; M.8 miscellaneous multi-site inhibitors: CH3Br, other alkyl halides, chloropicrin, sulfuryl fluoride, borax, tartar emetic;M.9 Chordotonal organ TRPV channel modulators: afidopyropen, pymetrozine; pyrifluquinazon;M.10 Mite growth inhibitors: clofentezine, hexythiazox, diflovidazin, etoxazole; M.11 Microbial disruptors of insect midgut membranes: bacillus thuringiensis, bacillus sphaericus, and insecticdal proteins they produce e.g.: bacillus thuringiensis subsp. israelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki, bacillusthuringiensis subsp. tenebrionis, Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A,Cry3Ab, Cry3Bb, Cry34 / 35Ab1; M.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron, organotin miticides, e.g.: azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon; M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient: chlorfenapyr,DNOC, sulfluramid;M.14 nAChR channel blockers: nereistoxin analogues bensultap, cartap hydrochloride, thio- cyclam, thiosultap-sodium; M.15 Inhibitors of the chitin biosynthesis type 0, e.g.: bistrifluron, chlorfluazuron, difluben-zuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron,triflumuron;M.16 Inhibitors of the chitin biosynthesis type 1: buprofezin; M.17 Moulting disruptors: Dipteran, cyromazine; 36 M.18 Ecdyson receptor agonists, e.g.: methoxyfenozide, tebufenozide, halofenozide, fufeno-zide, chromafenozide; M.19 Octopamin receptor agonists: amitraz; M.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon, acequinocyl,fluacrypyrim; bifenazate;M.21 METI acaricides and insecticides, e.g.: fenazaquin, fenpyroximate, pyrimidifen, pyrida-ben, tebufenpyrad, tolfenpyrad, rotenone; M.22 Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone, N-(3-chloro-2- methyl-phenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]-methylene]-hydrazinecarboxamide, N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide, 2-[2-(4-cyanophenyl)-1-[3- (trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide; M.23 Inhibitors of the of acetyl CoA carboxylase, e.g.: spirodiclofen, spiromesifen, spirotetramat; spiropidion; spirobudifen, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one, spidoxamat;M.24 Mitochondrial complex IV electron transport inhibitors: e.g. aluminium phosphide, calcium phosphide, zinc phosphide, cyanide; M.25 Mitochondrial complex II electron transport inhibitors, e.g.: cyenopyrafen, cyflumetofen, cyetpyrafen, pyflubumide;M.28 Ryanodine receptor-modulators: chlorantraniliprole, cyantraniliprole, cyclaniliprole,flubendiamide, fluchlordiniliprole, (R)-3-chloro-N1-{2-methyl-4-[1,2,2,2–tetrafluoro-1-(trifluoro- methyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid, (S)-3-chloro-N1-{2-methyl- 4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthal- amide, methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}ami-no)benzoyl]-1,2-dimethylhydrazine-carboxylate; N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methyl-phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide; 3-chloro-1-(3- chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H- pyrazole-5-carboxamide; tetrachlorantraniliprole; tetraniliprole; tiorantraniliprole; N-[4-chloro-2- [[(1,1-dimethylethyl)amino]carbonyl]-6-methyl-phenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; cyhalodiamide; N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide, pioxaniliprole; M.29: Chordotonal organ Modulators: flonicamid, flumetnicam; M.30: broflanilide; fluxametamide, isocycloseram, piperflanilide; M.33 acynonapyr;M.UN. Unknown mode of action: afoxolaner, azadirachtin, amidoflumet, ben-zoximate,bromopropylate, chinomethionat, cryolite, cyproflanilid, dicloromezotiaz, dicofol, dimpropyridaz, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, fluralaner, metaldehyde, metoxadiazone, mivorilaner, modoflaner, piperonyl butoxide, pyridalyl, tioxazafen, 37 trifluenfuronate, umifoxolaner, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9- azadispiro[4.2.4.2]-tetradec-11-en-10-one, 3-(4’-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8- oxa-1-azaspiro[4.5]dec-3-en-2-one, 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]- 3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine, actives on basis of bacillus firmus (Votivo, I-1582);fluazaindolizine; N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)-propyl]phe-nyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6- dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)-propyl]phenyl]carbamoyl]phenyl]-2-methyl- benzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoro- methyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; 1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2- a]pyridine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2- a]pyridin-5-ol; 1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; 2-(3-pyridinyl)-N-(2-pyrimidinylmethyl )-2H-indazole-5-carboxamide;tyclopyrazoflor; sarolaner, lotilaner; N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1- methyl-3-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide; N-[4- chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1,1,2,2,2-pentafluoroethyl)-4- (trifluoromethyl)-1H-pyrazole-5-carboxamide; 2-(3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(tri-fluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine; N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5- (1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide, N-[4-chloro-3-[(1- cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluorome- thyl)pyrazole-3-carboxamide; benzpyrimoxan; tigolaner; oxazosulfyl; [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl] N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2- yl] N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)- 3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl] N-[4-[1-[4-(1,1,2,2,2- pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl] N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(trifluorome- thoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one, (2Z)-3-(2- isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phe- nyl]methylenehydrazono]thiazolidin-4-one, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one; 2-(6-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5- b]pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoro- methyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-6-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6- 38 (trifluoromethyl)imidazo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3- methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyri- din-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-7-iodo-imida- zo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 3-ethylsulfonyl-6-iodo-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]imidazo[1,2-a]pyridine-8-carbonitrile, 2-[3-ethylsulfonyl-8-fluoro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoro- methyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3- methyl-6-(trifluoromethylsulfinyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imi- dazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine, 2-(6-bromo-3-ethyl-sulfonyl-imidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-c]pyridine; N-[[2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl]methyl]cy- clopropanecarboxamide; sulfiflumin; flupentiofenox, N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-2-me- thylsulfonyl-propanamide, cyclobutrifluram; N-[4-chloro-3-[(1-cyanocyclopro- pyl)carbamoyl]phenyl]-2-methyl-4-methylsulfonyl-5-(1,1,2,2,2-pentafluoroethyl)pyrazole-3-carboxamide, cyproflanilide, nicofluprole; 1,4-dimethyl-2-[2-(pyridin-3-yl)-2h-indazol-5-yl]-1,2,4-triazolidine-3,5-dione, indazapyroxamet, tiapyrachlor, N-cyclopropyl-5-[(5S)-5-(3,5-dichloro-4- fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]isoquinoline-8-carboxamide, 5-[(5S)-5-(3,5- dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(pyrimidin-2-ylmethyl)iso- quinoline-8-carboxamide, N-[1-(2,6-difluorophenyl)pyrazol-3-yl]-2-(trifluoromethyl)benzamide, 5-((1R,3R)-3-(3,5-Bis(trifluoromethyl)phenyl)-2,2-dichlorocyclopropane-1-carboxamido)-2-chloro-N-(3-(2,2-difluoroacetamido)-2,4-difluorophenyl)benzamide, 1-[6-(2,2-difluoro-7-methyl- [1,3]dioxolo[4,5-f]benzimidazol-6-yl)-5-ethylsulfonyl-3-pyridyl]cyclopropanecarbonitrile, 6-(5- cyclopropyl-3-ethylsulfonyl-2-pyridyl)-2,2-difluoro-7-methyl-[1,3]dioxolo[4,5-f]benzimidazole, Ledprona. Flupyroxystrobin, 3,5-bis(trifluoromethyl)-N-[(1S)-1-[1-[6-(trifluoromethyl)-4-pyrimidinyl]-1H-1,2,4-triazol-5-yl]ethyl]-benzamide, 2-(3-ethylsulfonyl-2-pyridyl)-5-(2,2,3,3,3-pentafluoropropoxy)pyrazine, 2-[3-ethylsulfonyl-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]-3- methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 9-(methoxymethyl)-5-(3-pyridyl)-2-oxa-5,6,9,14- tetrazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),3,6,11,13-pentaen-8-one, bisulfufen, 2-[5-[(E)-2- chloro-3,3,3-trifluoro-prop-1-enyl]-1-methyl-imidazol-2-yl]-5-cyclopropyl-3-ethylsulfonyl-pyridine,cybenzoxasulfyl, isoflualanam;Bentioflumin, Vadescana, (3Z)-1-[2-fluoro-4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3- yl]phenyl]-3-[3-[5-methyl-2-(2,2,2-trifluoroethoxymethyl)phenyl]-4-oxo-thiazolidin-2-ylidene]urea, 1-[6-(2,2-difluoro-8-oxo-[1,3]dioxolo[4,5-g]chromen-7-yl)-5-ethylsulfonyl-3- pyridyl]cyclopropanecarbonitrile, 2-chloro-N-[(1S)-2-ethyl-1-methyl-butyl]furan-3-carboxamide,galquin, [5-cyclopropyl-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]-3-pyridyl]-ethyl-hydroxy-oxo-λ⁶-sulfane, 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]- 2-methyl-N-[1-(2,2,2-trifluoroethylcarbamoyl)cyclopropyl]benzamide, 3-[3-ethylsulfonyl-7- (trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-7-(trifluoromethyl)chromen-4-one. 39 The commercially available compounds M listed above may be found in The Pesticide Manual, 18th Edition, C. MacBean, British Crop Protection Council (2018), or http: / / bcpcdata.com / pesticide-manual.html, http: / / www.alanwood.net / pesticides.The active compounds described by IUPAC nomenclature are known from CN103814937;WO2013 / 003977, WO2007 / 101369, WO2018 / 177970, CN10171577, CN102126994, WO2007 / 101540, WO2007 / 043677, WO2011 / 085575, WO2008 / 134969, WO2012 / 034403, WO2006 / 089633, WO2008 / 067911, WO2006 / 043635, WO2009 / 124707, WO2013 / 050317, WO2010 / 060379, WO2010 / 127926, WO2010 / 006713, WO2012 / 000896, WO2007 / 101369,WO2012 / 143317, WO2015 / 038503, EP2910126, WO2015 / 059039, WO2015 / 190316,WO2012 / 126766, WO2009 / 102736, WO2013 / 116053, WO2018 / 052136, WO2015150252, WO2020055955, WO2021158455, WO2013092350, WO201811111, EP3608311, WO2019236274, WO2013092350, WO 2018052136, WO2009102736, WO2016174049, WO2012126766, CN106554335, WO2017054524, CN105153113, WO2022072650;WO2018071327, WO2022101502, WO2012158396, WO2007079162, WO2020013147,WO2020097414, EP242081, WO2023058748, WO2017065228, EP3428166, WO2021029308, WO2022009058, WO2017067500, WO2020090585, WO2017146226, WO2021043115, WO2023016278, WO2021011722, WO2024126388, WO2024137594, EP4389739, WO2016096584, WO2024120137, WO2024188755, CN115925576, WO2024087613. The following list of fungicides, in conjunction with which the compounds of the invention can be used, illustrates the possible combinations:A) Respiration (C)- complex III at Qo site (QoI, C3): azoxystrobin (A.1.1), bifemetstrobin (A.1.24), bifujunzhi(A.1.37), coumethoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), ene-stroburin (A.1.5), famoxadone (A.1.21), fenamidone (A.1.23), fenaminstrobin (A.1.6), flufen- oxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin (A.1.11), metyltetraprole (A.1.25; member of MoA subgroup A), orysastrobin (A.1.12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), pyribencarb (A.1.19), pyriminostrobin (A.1.36), triclopyricarb(A.1.20), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxy- methyl)-phenyl)-2-methoxyimino-N-methyl-acetamide (A.1.18), methyl-N-[2-[(1,4-dimethyl- 5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1.22), (Z,2E)-5-[1-(2,4-di- chlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.34), (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide(A.1.35), 2-(ortho-((2,5-dimethylphenyl-oxymethylen)phenyl)-3-methoxy-acrylic acid methylester (A.1.38), methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]- prop-2-enoate, methyl (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop- 40 2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop- 2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoate, methyl (Z)-2-[5-(4-isopropyltriazol-2-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclobutyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclopent-yl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclopropyl-2-methyl-phen- oxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy- prop-2-enoate, methyl (E)-3-methoxy-2-[(2-methyl-5-phenyl-phenyl)methyl]prop-2-enoate, methyl (E)-3-methoxy-2-[[5-[(E)-N-methoxy-C-methyl-carbonimidoyl]-2,4-dimethyl-phenyl]- methyl]prop-2-enoate; methyl (E)-2-[[5-(2-cyclopropylethynyl)-2,4-dimethyl-phenyl]methyl]-3-methoxy-prop-2-enoate; methyl (E)-3-methoxy-2-(2-phenyl-1,3-benzoxazol-4-yl)prop- 2-enoate; methyl (E)-3-methoxy-2-(2-phenyl-1,3-benzothiazol-4-yl)prop-2-enoate; methyl (E)-3-methoxy-2-(2-phenyl-1,3-benzoxazol-7-yl)prop-2-enoate; methyl (Z)-2-[6-(2-cycloprop- ylethynyl)benzimidazol-1-yl]-3-methoxy-prop-2-enoate; methyl (Z)-3-methoxy-2-(6-phenyl- benzimidazol-1-yl)prop-2-enoate; methyl (Z)-2-(3-chloro-6-phenyl-indol-1-yl)-3-methoxy-prop-2-enoate; methyl (Z)-2-(2,3-dichloro-6-phenyl-indol-1-yl)-3-methoxy-prop-2-enoate; methyl (Z)-3-methoxy-2-[6-[(E)-methoxyiminomethyl]indol-1-yl]prop-2-enoate; methyl (Z)-3-methoxy-2-[6-[(E)-N-methoxy-C-methyl-carbonimidoyl]indol-1-yl]prop-2-enoate, methyl N-[[5-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate, methyl N-[[5-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]-carbamate, methyl N-[[5-[1-(4-chloro-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]- methyl]carbamate, methyl N-[[5-[1-[2,6-difluoro-4-(trifluoromethyl)phenyl]pyrazol-3-yl]- 2-methyl-phenyl]methyl]carbamate;- complex III at Qi site (QiI, C4): cyazofamid (A.2.1), amisulbrom (A.2.2), [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]-2-methylpropanoate (A.2.3), fenpicoxamid (A.2.4), florylpicoxamid (A.2.5), metarylpicoxamid (A.2.6);- complex II (SDHI, C2): benodanil (A.3.1), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid(A.3.4), carboxin (A.3.5), cyclobutrifluram (A.3.24), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), inpyrfluxam (A.3.22), isofetamid(A.3.11), isoflucypram (A.3.31), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyrapropoyne (A.3.23), pyraziflumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21), fluindapyr (A.3.28), N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)- 5-fluoro-1-methyl-pyrazole-4-carboxamide (A.3.29), methyl (E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate (A.3.30), 2-(difluoromethyl)- N-(1,1,3-trimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)- N-[(3R)-1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)- 41 N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)- N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)- N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)- N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)- N-(3-isobutyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.39);- complex I NADH oxido-reductase (C1): diflumetorim (A.4.1);- uncouplers (C5): binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5),meptyldinocap (A.4.6), ferimzone (A.4.7);- inhibitors of ox. phosphorylation (C6): fentin salts, e.g. fentin-acetate (A.4.8), fentin chloride(A.4.9) or fentin hydroxide (A.4.10);- ATP transport: silthiofam (A.4.11);- quinone inside and outside inhibitor stigmatellin binding type (QioSI; C8): ametoctradin(A.5.1);B) Sterol biosynthesis (G)- C14 demethylase (DMI, G1): triazoles: azaconazole (B.1.1), bitertanol (B.1.2), bromuconazole(B.1.3), cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluoxytioconazole (B.1.33), fluquinconazole (B.1.10), flusilazole (B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13), imi- benconazole (B.1.14), ipconazole (B.1.15), ipfentrifluconazole (B.1.37), mefentrifluconazole(B.1.38), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole (B.1.20), penconazole (B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1.30), 2-(2,4-difluorophenyl)- 1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol(B.1.31), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]- 2-pyridyl]propan-2-ol (B.1.32), 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1,2,4-triazol- 1-ylmethyl)cyclopentanol (B.1.43), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy- 3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile (B.1.53), 2-[6-(4-bromophenoxy)- 2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (B.1.54), 2-[6-(4-chlorophen-oxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (B.1.55), (2R)-2-[4-(4-chlo- rophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (2S)-2-[4-(4-chlo- rophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, methyl 2-[2-chloro- 4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate (B.1.56), 2-[2-chloro- 4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid (B.1.57); imid-azoles: imazalil (B.1.44), pefurazoate (B.1.45), prochloraz (B.1.46), triflumizole (B.1.47); pyrimidines, pyridines, piperazines: fenarimol (B.1.49), pyrifenox (B.1.50), triforine (B.1.51), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol 42 (B.1.52);- delta14-reductase (G2): aldimorph (B.2.1), dodemorph (B.2.2), dodemorph-acetate (B.2.3),fenpropidin (B.2.6), fenpropimorph (B.2.4), piperalin (B.2.7), spiroxamine (B.2.8), tridemorph (B.2.5);- 3-keto reductase (G3): fenhexamid (B.3.1), fenpyrazamine (B.3.2);- other: chlorphenomizole (B.4.1);C) Nucleic acids metabolism (A)- RNA polymerase I (A1): benalaxyl (C.1.1), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl(C.1.4), metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);- adenosine deaminase (A2): bupirimate (C.2.4), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine(C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro-2-(4-chloro- phenylmethoxy)pyrimidin-4-amine (C.2.8);- DNA / RNA synthesis (A3): 5-fluorocytosine (C.2.5), hymexazole (C.2.1), octhilinone (C.2.2),- gyrase (A4): oxolinic acid (C.2.3);- dihydroorotate dehydrogenase (DHODH; A5): ipflufenoquin (C.5.1), quinofumelin (C.5.2),feneptamidoquin (C.5.3);D) Cytoskeleton and motor protein (B)- tubulin polymerization (MBC; B1): benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D.1.3),pyridachlometyl (D.1.6), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), N-ethyl- 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- N-(2-fluoroethyl)butanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroeth- yl)-2-methoxy-acetamide (D.1.11), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl- butanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-acetamide(D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol- 3-amine (D.1.16), 4-(2-bromo-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl- 1H-pyrazol-5-amine, 4-(2-chloro-4,6-difluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl- 1H-pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-3-ethyl-1-methyl-1H-pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-4-methyl-6-nitrophenyl)-1,3-di- methyl-1H-pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-di- methyl-1H-pyrazol-5-amine, 4-(2,4-difluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl- 1H-pyrazol-5-amine;- tubulin polymerization (B2): diethofencarb (D.2.1),- tubulin polymerization (B3): ethaboxam (D.2.2), zoxamide (D.2.5);- cell division (B4): pencycuron (D.2.3);- spectrin-like proteins (B5): fluopicolide (D.2.4), fluopimomide (D.2.9); 43- actin / myosin / fimbrin function (B6): metrafenone (D.2.6), phenamacril (D.2.8), pyriofenone(D.2.7);E) Amino acids and protein synthesis (D)- methionine synthesis (D1): cyprodinil (E.1.1), mepanipyrim (E.1.2), pyrimethanil (E.1.3);- ribosome, termination step (D2): blasticidin-S (E.2.1);- ribosome initiation step (D3): kasugamycin (E.2.2), kasugamycin hydrochloride-hydrate(E.2.3);- ribosome initiation step (D4): streptomycin (E.2.5);- ribosome elongation step (D5): mildiomycin (E.2.4), oxytetracyclin (E.2.6);F) Signal transduction- mechanism unknown (E1): proquinazid (F.2.2), quinoxyfen (F.2.1);- MAP / histidine kinase os-2 (E2): fludioxonil (F.1.5);- MAP / histidine kinase os-1 (E3): iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4);G) Lipid synthesis or transport / membrane (F)- methyl transferase (F2): edifenphos (G.1.1), iprobenfos (G.1.2), isoprothiolane (G.1.4);pyrazophos (G.1.3);- cell peroxidation (F3): biphenyl (G.2.5), chloroneb (G.2.6), dicloran (G.2.1), etridiazole (G.2.7),quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4);- cell membrane permeability (F4): propamocarb (G.4.1);- ergosterol binding (F8): natamycin;- oxysterol binding protein (F9): fluoxapiprolin (G.5.3), oxathiapiprolin (G.5.1), 4-[1-[2-[3-(di-fluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.4), 4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyri- dine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]- 4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoro-methyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine- 2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-pi- peridyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)pyr- azol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cy-clopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carbox- amide (G.5.11), (1-(4-(4-(5-(2,6-dichlorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)piper- idin-1-yl)-2-((3-trifluoromethyl)pyrazin-2-yl)oxy)ethan-1-one, 1-(4-(4-(5-(2-chloro-6-fluoro- phenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)piperidin-1-yl)-2-((3-trifluoromethyl)pyridin-2-yl)- oxy)ethan-1-one, tert-butyl 4-(4-(5-(2-bromo-6-fluorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)piperidin-1-carboxylate, ((2-(3-(2-(1-(2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)acetyl)- piperidin-4-yl)thiazol-4-yl)-4,5-dihydroisoxazo-5-yl)-3-fluorophenyl)imino)dimethyl-λ6-sulfa- none, ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol- 44 4-yl)-4,5-dihydroisoxazo-5-yl)-3-fluorophenyl)imino)dimethyl-λ6-sulfanone, ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol-4-yl)- 4,5-dihydroisoxazo-5-yl)-3-chorophenyl)imino)(isopropyl)(methyl)-λ6-sulfanone, ((2-(3-(2-(1-(2-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol-4-yl)- 4,5-dihydroisoxazo-5-yl)-3-fluorophenyl)imino)(isopropyl)(methyl)-λ6-sulfanone,((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol-4-yl)- 4,5-dihydroisoxazo-5-yl)-3-(trifluoromethyl)phenyl)imino)dimethyl-λ6-sulfanone, ((3-fluoro- 2-(3-(2-(1-(2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol-4-yl)- 4,5-dihydroisoxazo-5-yl)-phenyl)imino)dimethyl-λ6-sulfanone;H) Multi Site Activity (M)- inorganics (M01): Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copperhydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7);- dithiocarbamates and relatives: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam(H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9), zinc thiazole (H.2.10);- organochlorine compounds (M04, M05, M06, M08): anilazine (H.3.1), captafol (H.3.3), captan(H.3.4), chlorothalonil (H.3.2), dichlofluanid (H.3.6), dichlorophen (H.3.7), folpet (H.3.5), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.11);- guanidines, quinones, quinoxalines, maleimides, thiocarbamates (M07, M09, M10, M11,M12): chinomethionat (H.4.13), dithianon (H.4.9), fluoroimide (H.4.11), guanidine (H.4.1), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), methasulfocarb (H.4.12), 2,6-dimethyl- 1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone (H.4.10),I) Cell wall biosynthesis (H) and melanin synthesis in cell wall (I)- chitin synthase (H4): polyoxin B (I.1.2);- cellulose synthase (H5): benthiavalicarb (I.3.5), dimethomorph (I.3.1), flumorph (I.3.2),iprovalicarb (I.3.6), mandipropamid (I.3.3), pyrimorph (I.3.4), valifenalate (I.3.7);- reductase in melanin synthesis (MBI-R; I1) pyroquilon (I.2.1), tricyclazole (I.2.2);- dehydratase in melanin synthesis (MBI-D, I2); carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil(I.2.5);- polyketide synthase in melanin synthesis (MBI-P, I3): tolprocarb (I.2.6);J) Plant defense induction (P1 to P8)- salicylate-related (P01-P03, P08): acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil(J.1.3), tiadinil (J.1.4), dichlobentiazox (J.1.13); phosphonates (P07): fosetyl (J.1.6), fosetyl-aluminum (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.11), potassium phosphonate (J.1.12); others: potassium or sodium bicarbonate (J.1.9), 4-cyclo- propyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1.10); 45K) Unknown mode of action (U)- aminopyrifen (K.1.54), benziothiazolinone (K.1.48), bromothalonil (K.1.49), bronopol (K.1.1),cyflufenamid (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclomezine (K.1.8), difenzoquat (K.1.9), difenzoquat-methylsulfate (K.1.10), diphenylamin (K.1.11), dodine, dodine free base (K.1.18), fenitropan (K.1.12), flufenoxadiazam (K.1.58) [MoAproposed: class II histone deacetylase inhibitor], flumetover (K.1.14), flumetylsulforim (K.1.60), flusulfamide (K.1.15), flutianil (K.1.16), harpin (K.1.17), nitrapyrin (K.1.19), nitrothal- isopropyl (K.1.20), oxine-copper (K.1.22), picarbutrazox (K.1.41), pyrisoxazole (K.1.37), seboctylamine (K.1.61), tebufloquin (K.1.24), tecloftalam (K.1.25), triazoxide (K.1.26), validamycin (K.1.2); N’-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine (K.1.27), N’-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl- phenyl)-N-ethyl-N-methyl formamidine (K.1.28), N’-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thia- diazol-5-yl]oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.29), N’-(5-bromo- 6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (K.1.30), N’-[5-bromo- 6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.31),N’-[5-bromo-6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.32), N’-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.33), N’-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl- N-methyl formamidine (K.1.34), N’-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)- phenyl)-N-ethyl-N-methyl formamidine (K.1.35), 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide (K.1.36), 3-[5-(4-methylphenyl)-2,3-di- methyl-isoxazolidin-3-yl]-pyridine (K.1.38), 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-meth- yl-1H-benzoimidazole (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1.40), pentyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carba- mate (K.1.42), but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxy-methyl]-2-pyridyl]carbamate (K.1.43), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[6-(3-flu- oro-4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51), N’-(2,5-dimethyl-4-phenoxy- phenyl)-N-ethyl-N-methyl-formamidine (K.1.53), N'-[5-bromo-2-methyl-6-(1-methyl-2-prop- oxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.56), N'-[4-(4,5-dichlorothiazol- 2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.57), N-methyl-4-[5-(tri-fluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide (K.1.59), N-methoxy-N-[[4-[5-(tri- fluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (K.1.61), N-((4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl)methyl)propanamide (K.1.62), 3,3,3-tri- fluoro-N-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.63), 3,3,3-trifluoro-N-[[2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-propanamide (K.1.64), N-[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl]- butanamide (K.1.65), N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]- methyl]-3,3,3-trifluoro-propanamide (K.1.66), 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl)- 46 1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.67), 1,1-diethyl-3-[[4-[5-[trifluoromethyl]- 1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.68), N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.69), N-ethyl-2-methyl-N-[[4-[5-(trifluoro- methyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.70), 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.71), 1-[[4-[5-(trifluoro-methyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.72), 1-[[4-[5-(trifluoro- methyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one (K.1.73), 4-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]morpholin-3-one (K.1.74), 4,4-dimethyl-2-[[4-[5-(trifluoro- methyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.75), 2-[[4-[5-(trifluoro-methyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.76), 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.77), 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one (K.1.78), 2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]oxazinan-3-one (K.1.79), 1-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one(K.1.80), 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.81), 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]- pyrrolidin-2-one (K.1.82), ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]- pyrazole-4-carboxylate (K.1.83), N-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]- phenyl]methyl]pyrazole-4-carboxamide (K.1.84), N,N-dimethyl-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl]-1H-1,2,4-triazol-3-amine (K.1.85), N-methoxy-N-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.86), propyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.87), N-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole- 4-carboxamide (K.1.88), N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phen-yl]methyl]propanamide (K.1.89), 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.90), 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl]phenyl]methyl]urea (K.1.91), N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl]phenyl]methyl]acetamide (K.1.92), N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]- benzyl]cyclopropanecarboxamide (K.1.93), 1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadi-azol-3-yl]phenyl]methyl]urea (K.1.94), N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.95), N'-[2-chloro-4-[(4-methoxy-phenyl)methyl]-5-methyl- phenyl]-N-ethyl-N-methyl-formamidine (K.1.96), N'-[2-chloro-4-[(4-cyano-phenyl)methyl]- 5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.97), N'-[2,5-dimethyl-4-(o-tolylmethyl)- phenyl]-N-ethyl-N-methyl-formamidine (K.1.98), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.99),3-(3-bromo-2-fluoro-phenoxy)-6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]- 5-methyl-pyridazine-4-carboxamide (K.1.100), 6-chloro-N-[2-(2-chloro-4-methyl-phenyl)- 2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide 47 (K.1.101), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-diflu- oro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.102), 6-chloro-3-(3-chloro-2-fluoro-phen- oxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.103), N-[2-(2-bromo-4-methyl-phenyl)-2,2-difluoro-ethyl]-6-chloro-3-(3-cyclopropyl-2-flu- oro-phenoxy)-5-methyl-pyridazine-4-carboxamide (K.1.104), 2-[cyano-(2,6-difluoro-4-pyri-dyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4-carboxamide, 2-[acetyl-(2,6-difluoro- 4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, 2-[(2,6-di- fluoro-4-pyridyl)-(2-methoxyacetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole- 4-carboxamide, 2-[cyano-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl- thiazole-4-carboxamide, N-[1-[[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]-5-[(Z)-N-isopropoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]methyl]-2-methyl- propyl]-2-methyl-propanamide, N-[1-[[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]- 5-[(Z)-N-isopropoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]methyl]-2-methyl- propyl]-2,2-dimethyl-propanamide, N-[2-[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]- 5-[(Z)-N-isopropoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propanamide, N-[2-[3-[2-hydroxy-2-(2-methoxyphenyl)ethyl]-5-[(Z)-N-isopropoxy- C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propanamide, N-[2-[3-[2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxy-phenyl)ethyl]-5-[(Z)-N-isopropoxy-C-meth- yl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propanamide, rac-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)-methyl]-5,6-dihydro-4H-1,2,4-oxadiazine, (5S)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl- pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine, (5R)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)- methyl]-5,6-dihydro-4H-1,2,4-oxadiazine, 2-(4-fluorophenoxy)-1-[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]ethanone, 2-[(6-fluoro-3-pyridyl)oxy]-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanone, 2-(4-fluoroanilino)-1-[4-[5-(trifluoromethyl)-1,2,4-oxa- diazol-3-yl]phenyl]ethenone, ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]- phenyl]methyl]-1H-pyrazole-4-carboxylate, ethyl 1-[[4-[[(1Z)-2-ethoxy-3,3,3-trifluoro-1-pro- pen-1-yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate; The fungicides described by common names, their preparation and their activity e.g. against harmful fungi is known (cf.: http: / / www.alanwood.net / pesticides / ); these substances are commercially available. The active substances, their preparation and their activity e.g. against fungi is known(www.bcpcpesticidecompendium.bcpc.org / ); many of them are commercially available.Compounds defined by IUPAC nomenclature, their preparation and pesticidal activity are also known (e.g. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-141317; EP-152031; EP-226917; EP-243970; EP-256503; EP-428941; EP-532022; EP-1028125; EP-1035122; 48 EP-1201648; EP-1122244, JP2002316902; DE19650197; DE10021412; DE102005009458; US 3,296,272; US 3,325,503; WO 98 / 46608; WO 99 / 14187; WO 99 / 24413; WO 99 / 27783; WO 00 / 29404; WO 00 / 46148; WO 00 / 65913; WO 01 / 54501; WO 01 / 56358; WO 02 / 22583; WO 02 / 40431; WO 03 / 10149; WO 03 / 11853; WO 03 / 14103; WO 03 / 16286; WO 03 / 53145;WO 03 / 61388; WO 03 / 66609; WO 03 / 74491; WO 04 / 49804; WO 04 / 83193; WO 05 / 120234;WO 05 / 123689; WO 05 / 123690; WO 05 / 63721; WO 05 / 87772; WO 05 / 87773; WO 06 / 15866; WO 06 / 87325; WO 06 / 87343; WO 07 / 82098; WO 07 / 90624, WO 10 / 139271, WO 11 / 028657, WO 12 / 168188, WO 07 / 006670, WO 11 / 77514; WO 13 / 047749, WO 10 / 069882, WO 13 / 047441, WO 03 / 16303, WO 09 / 90181, WO 13 / 007767, WO 13 / 010862, WO 13 / 127704, WO 13 / 024009,WO 13 / 24010, WO 13 / 047441, WO 13 / 162072, WO 13 / 092224, WO 11 / 135833, CN 1907024,CN 1456054, CN 103387541, CN 1309897, WO 12 / 84812, CN 1907024, WO 09094442, WO 14 / 60177, WO 13 / 116251, WO 08 / 013622, WO 15 / 65922, WO 94 / 01546, EP 2865265, WO 07 / 129454, WO 12 / 165511, WO 11 / 081174, WO 13 / 47441, WO 16 / 156241, WO 16 / 162265, WO 23 / 99460, WO 21 / 244950, WO 21 / 244951, WO 22 / 130188, WO 22 / 243810, WO 21 / 255070,WO 21 / 176057, WO 21 / 153754, JP2023064110, JP2022153603, JP2022046550,JP2022031355, WO 22 / 249074, WO 23 / 046861, WO 18 / 177894, WO 20 / 212513, WO 20 / 097012, US 2023 / 0069915. Some compounds are identified by their CAS Registry Number.BiopesticidesSuitable mixing partners for the compounds of the invention also include biopesticides. Biopesticides have been defined as a form of pesticides based on micro-organisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds, e.g. metabolites, proteins, or extracts from biological or other natural sources) (U.S. Environmental Protection Agency:http: / / www.epa.gov / pesticides / biopesticides / ). Biopesticides fall into two major classes, microbialand biochemical pesticides:(1) Microbial pesticides consist of bacteria, fungi or viruses (and often include the metabolitesthat bacteria and fungi produce). Entomopathogenic nematodes are also classified as microbial pesticides, even though they are multi-cellular.(2) Biochemical pesticides are naturally occurring substances or structurally-similar andfunctionally identical to a naturally-occurring substance and extracts from biological sources that control pests or provide other crop protection uses as defined below, but have non-toxic mode of actions (e.g. growth or developmental regulation, attractants, repellents or defense activators (e.g. induced resistance) and are relatively non-toxic to mammals.The following list of biopesticides, in conjunction with which the compounds of the invention canbe used, illustrates the possible combinations: L) Biopesticides 49L1) Microbial pesticides with fungicidal, bactericidal, viricidal and / or plant defenseactivator activity: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. amyloliquefaciens ssp. plantarum (also referred to as B. velezensis), B. megaterium, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B.solisalsi, B. subtilis, B. subtilis var. amyloliquefaciens, B. velezensis, Candida oleophila, C.saitoana, Clavibacter michiganensis (bacteriophages), Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f. catenulate (also named Gliocladium catenulatum), Gliocladium roseum, Lysobacter antibioticus, L. enzymogenes, Metschnikowia fructicola, Microdochiumdimerum, Microsphaeropsis ochracea, Muscodor albus, Paenibacillus alvei, Paenibacillusepiphyticus, P. polymyxa, Pantoea vagans, Penicillium bilaiae, Phlebiopsis gigantea, Pseudomonas sp., Pseudomonas chloraphis, Pseudozyma flocculosa, Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces griseoviridis, S. lydicus, S. violaceusniger, Talaromyces flavus, Trichoderma asperelloides, T. asperellum, T. atroviride,T. fertile, T. gamsii, T. harmatum, T. harzianum, T. polysporum, T. stromaticum, T. virens, T.viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahliae, zucchini yellow mosaic virus (avirulent strain);L2) Biochemical pesticides with fungicidal, bactericidal, viricidal and / or plant defenseactivator activity: harpin protein, plant oils (BM3): tea tree oil, orange oil (L.2.1), eugenol,limonene (L.2.2), geraniol (L.2.3), thymol (L.2.4); Reynoutria sachalinensis extract,aureobasidin (in particular aureobasidin A (L.2.5)), ambruticin (L.2.6), bafilomycin (L.2.7) (in particular bafilomycin A1, B1 and C1), chlorflavonin (L.2.8), cinnamaldehyde (L.2.9), natamycin (L.2.10; F8);L3) Microbial pesticides with insecticidal, acaricidal, molluscidal and / or nematicidalactivity: Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B.thuringiensis ssp. aizawai, B. t. ssp. israelensis, B. t. ssp. galleriae, B. t. ssp. kurstaki, B. t. ssp. tenebrionis, Beauveria bassiana, B. brongniartii, Burkholderia spp., Chromobacterium subtsugae, Cydia pomonella granulovirus (CpGV), Cryptophlebia leucotreta granulovirus (CrleGV), Flavobacterium spp., Helicoverpa armigera nucleopolyhedrovirus (HearNPV),Helicoverpa zea nucleopolyhedrovirus (HzNPV), Helicoverpa zea single capsidnucleopolyhedrovirus (HzSNPV), Heterorhabditis bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, L. muscarium, Metarhizium anisopliae, M. anisopliae var. anisopliae, M. anisopliae var. acridum, Nomuraea rileyi, Paecilomyces fumosoroseus, P. lilacinus, Paenibacillus popilliae, Pasteuria spp., P. nishizawae, P. penetrans, P. ramosa, P.thornea, P. usgae, Pseudomonas fluorescens, Spodoptera littoralis nucleopolyhedrovirus(SpliNPV), Steinernema carpocapsae, S. feltiae, S. kraussei, Streptomyces galbus, S. microflavus; 50 L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal, pheromone and / ornematicidal activity: L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, (E,Z)-2,4-ethyl decadienoate (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavanulyl senecioate, cis-jasmone, 2-methyl-1-butanol, methyl eugenol, methyl jasmonate, (E,Z)-2,13-octadecadien-1-ol, (E,Z)-2,13-octadecadien-1-ol acetate,(E,Z)-3,13-octadecadien-1-ol, (R)-1-octen-3-ol, pentatermanone, (E,Z,Z)-3,8,11-tetradecatrienyl acetate, (Z,E)-9,12-tetradecadien-1-yl acetate, (Z)-7-tetradecen-2-one, (Z)-9-tetradecen-1-yl acetate, (Z)-11-tetradecenal, (Z)-11-tetra- decen-1-ol, extract of Chenopodium ambrosiodes, Neem oil, Quillay extract; L5) Microbial pesticides with plant stress reducing, plant growth regulator, plant growthpromoting and / or yield enhancing activity: Azospirillum amazonense, A. brasilense, A. lipoferum, A. irakense, A. halopraeferens, Bradyrhizobium spp., B. elkanii, B. japonicum, B. liaoningense, B. lupini, Delftia acidovorans, Glomus intraradices, Mesorhizobium spp., Rhizobium leguminosarum bv. phaseoli, R. l. bv. trifolii, R. l. bv. viciae, R. tropici, Sinorhizobium meliloti.The biopesticides from group L1) and / or L2) may also have insecticidal, acaricidal, molluscidal, pheromone, nematicidal, plant stress reducing, plant growth regulator, plant growth promoting and / or yield enhancing activity. The biopesticides from group L3) and / or L4) may also have fungicidal, bactericidal, viricidal, plant defense activator, plant stress reducing, plant growthregulator, plant growth promoting and / or yield enhancing activity. The biopesticides from groupL5) may also have fungicidal, bactericidal, viricidal, plant defense activator, insecticidal, acaricidal, molluscidal, pheromone and / or nematicidal activity. Many of these biopesticides have been deposited under deposition numbers mentioned herein (the prefices e.g. ATCC or DSM refer to the acronym of the respective culture collection, for detailssee e.g. here: http: / / www. wfcc.info / ccinfo / collection / by_acronym / ), are referred to in literature,registered and / or are commercially available: mixtures of Aureobasidium pullulans DSM 14940 and DSM 14941 isolated in 1989 in Konstanz, Germany (e.g. blastospores in BlossomProtect® from bio-ferm GmbH, Austria), Azospirillum brasilense Sp245 originally isolated in wheat reagion of South Brazil (Passo Fundo) at least prior to 1980 (BR 11005; e.g. GELFIX® Gramíneas fromBASF Agricultural Specialties Ltd., Brazil), A. brasilense strains Ab-V5 and Ab-V6 (e.g. in AzoMaxfrom Novozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazil or Simbiose- Maíz® from Simbiose-Agro, Brazil; Plant Soil 331, 413-425, 2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331; US8,445,255); B. amylo-liquefaciens ssp. plantarum strains formerly also sometimes referred to as B. subtilis, recently together with B.methylotrophicus, and B. velezensis classified as B. velezensis (Int. J. Syst. Evol. Microbiol. 66,1212–1217, 2016): B. a. ssp. plantarum or B. velezensis D747 isolated from air in Kikugawashi, Japan (US 20130236522 A1; FERM BP 8234; e.g. Double Nickel™ 55 WDG from Certis LLC, USA), B. a. ssp. plantarum or B. velezensis FZB24 isolated from soil in Brandenburg, Germany 51 (also called SB3615; DSM 96-2; J. Plant Dis. Prot. 105, 181–197, 1998; e.g. Taegro® from Novozyme Biologicals, Inc., USA), B. a. ssp. plantarum or B. velezensis FZB42 isolated from soil in Brandenburg, Germany (DSM 23117; J. Plant Dis. Prot.105, 181–197, 1998; e.g. RhizoVital® 42 from AbiTEP GmbH, Germany), B. a. ssp. plantarum or B. velezensis MBI600 isolated fromfaba bean in Sutton Bonington, Nottinghamshire, U.K. at least before 1988 (also called 1430;NRRL B 50595; US 2012 / 0149571 A1; e.g. Integral® from BASF Corp., USA), B. a. ssp. plantarum or B. velezensis QST-713 isolated from peach orchard in 1995 in California, U.S.A. (NRRL B 21661; e.g. Serenade® MAX from Bayer Crop Science LP, USA), B. a. ssp. plantarum or B. velezensis TJ1000 isolated in 1992 in South Dakoda, U.S.A. (also called 1BE; ATCC BAA-390; CA 2471555 A1; e.g. QuickRoots™ from TJ Technologies, Watertown, SD, USA); B. firmusCNCM I-1582, a variant of parental strain EIP-N1 (CNCM I-1556) isolated from soil of central plain area of Israel (WO 2009 / 126473, US6,406,690; e.g. Votivo® from Bayer CropScience LP, USA), B. pumilus GHA 180 isolated from apple tree rhizo-sphere in Mexico (IDAC 260707-01; e.g. PRO- MIX® BX from Premier Horticulture, Quebec, Canada), B. pumilus INR-7 otherwise referred to asBU F22 and BU-F33 isolated at least be-fore 1993 from cucumber infested by Erwinia tracheiphila(NRRL B-50185, NRRL B-50153; US 8,445,255), B. pumilus KFP9F isolated from the rhizosphere of grasses in South Africa at least before 2008 (NRRL B-50754; WO 2014 / 029697; e.g. BAC-UP or FUSION-P from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. pumilus QST 2808 was isolated from soil collected in Pohnpei, Federated States of Micronesia, in 1998 (NRRL B30087; e.g. Sonata® or Ballad® Plus from Bayer Crop Science LP, USA), B. simplex ABU 288(NRRL B-50304; US8,445,255), B. subtilis FB17 also called UD 1022 or UD10-22 isolated from red beet roots in North America (ATCC PTA-11857; System. Appl. Microbiol.27, 372-379, 2004; US2010 / 0260735; WO 2011 / 109395); B. thuringiensis ssp. aizawai ABTS-1857 isolated from soil taken from a lawn in Ephraim, Wisconsin, U.S.A., in 1987 (also called ABG 6346; ATCC SD-1372; e.g. XenTari® from BioFa AG, Münsingen, Germany), B. t. ssp. kurstaki ABTS-351 identicalto HD-1 isolated in 1967 from diseased Pink Bollworm black larvae in Brownsville, Texas, U.S.A. (ATCC SD-1275; e.g. Dipel® DF from Valent BioSciences, IL, USA), B. t. ssp. kurstaki SB4 isolated from E. saccharina larval cadavers (NRRL B-50753; e.g. Beta Pro® from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. t. ssp. tenebrionis NB-176-1, a mutant of strainNB‑125, a wild type strain isolated in 1982 from a dead pupa of the beetle Tenebrio molitor (DSM5480; EP 585215 B1; e.g. Novodor® from Valent BioSciences, Switzerland), Beauveria bassiana GHA (ATCC 74250; e.g. BotaniGard® 22WGP from Laverlam Int. Corp., USA), B. bassiana JW- 1 (ATCC 74040; e.g. Naturalis® from CBC (Europe) S.r.l., Italy), B. bassiana PPRI 5339 isolated from the larva of the tortoise beetle Conchyloctenia punctata (NRRL 50757; e.g. BroadBand®from BASF Agricultural Specialities (Pty) Ltd., South Africa), Bradyrhizobium elkanii strainsSEMIA 5019 (also called 29W) isolated in Rio de Janeiro, Brazil and SEMIA 587 isolated in 1967 in the State of Rio Grande do Sul, from an area previously inoculated with a North American 52 isolate, and used in commercial inoculants since 1968 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e.g. GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum 532c isolated from Wisconsin field in U.S.A. (Nitragin 61A152; Can. J. Plant. Sci. 70, 661-666, 1990; e.g. in Rhizoflo®, Histick®, Hicoat® Super from BASF Agricultural Specialties Ltd., Canada), B.japonicum E-109 variant of strain USDA 138 (INTA E109, SEMIA 5085; Eur. J. Soil Biol.45, 28–35, 2009; Biol. Fertil. Soils 47, 81–89, 2011); B. japonicum strains deposited at SEMIA known from Appl. Environ. Microbiol. 73(8), 2635, 2007: SEMIA 5079 isolated from soil in Cerrados region, Brazil by Embrapa-Cerrados used in commercial inoculants since 1992 (CPAC 15; e.g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum SEMIA5080 obtained under lab conditions by Embrapa-Cerrados in Brazil and used in commercialinoculants since 1992, being a natural variant of SEMIA 586 (CB1809) originally isolated in U.S.A. (CPAC 7; e.g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil); Burkholderia sp. A396 isolated from soil in Nikko, Japan, in 2008 (NRRL B-50319; WO 2013 / 032693; Marrone Bio Innovations, Inc., USA), Coniothyrium minitans CON / M / 91-08 isolatedfrom oilseed rape (WO 1996 / 021358; DSM 9660; e.g. Contans® WG, Intercept® WG from BayerCropScience AG, Germany), harpin (alpha-beta) protein (Science 257, 85-88, 1992; e.g. Messenger™ or HARP-N Tek from Plant Health Care plc, U.K.), Helicoverpa armigera nucleopolyhedrovirus (HearNPV) (J. Invertebrate Pathol.107, 112–126, 2011; e.g. Helicovex® from Adermatt Biocontrol, Switzerland; Diplomata® from Koppert, Brazil; Vivus® Max fromAgBiTech Pty Ltd., Queensland, Australia), Helicoverpa zea single capsid nucleopolyhedrovirus(HzSNPV) (e.g. Gemstar® from Certis LLC, USA), Helicoverpa zea nucleopolyhedrovirus ABA- NPV-U (e.g. Heligen® from AgBiTech Pty Ltd., Queensland, Australia), Heterorhabditis bacteriophora (e.g. Nemasys® G from BASF Agricultural Specialities Limited, UK), Isaria fumosorosea Apopka-97 isolated from mealy bug on gynura in Apopka, Florida, U.S.A. (ATCC20874; Biocontrol Science Technol. 22(7), 747-761, 2012; e.g. PFR-97™ or PreFeRal® fromCertis LLC, USA), Metarhizium anisopliae var. anisopliae F52 also called 275 or V275 isolated from codling moth in Austria (DSM 3884, ATCC 90448; e.g. Met52® Novozymes Biologicals BioAg Group, Canada), Metschnikowia fructicola 277 isolated from grapes in the central part of Israel (US 6,994,849; NRRL Y-30752; e.g. formerly Shemer® from Agrogreen, Israel),Paecilomyces ilacinus 251 isolated from infected nematode eggs in the Philippines (AGAL89 / 030550; WO1991 / 02051; Crop Protection 27, 352-361, 2008; e.g. BioAct®from Bayer CropScience AG, Germany and MeloCon® from Certis, USA), Paenibacillus alvei NAS6G6 isolated from the rhizosphere of grasses in South Africa at least before 2008 (WO 2014 / 029697; NRRL B-50755; e.g. BAC-UP from BASF Agricultural Specialities (Pty) Ltd., South Africa),Paenibacillus strains isolated from soil samples from a variety of European locations includingGermany: P. epiphyticus Lu17015 (WO 2016 / 020371; DSM 26971), P. polymyxa ssp. plantarum Lu16774 (WO 2016 / 020371; DSM 26969), P. p. ssp. plantarum strain Lu17007 (WO 2016 / 020371; DSM 26970); Pasteuria nishizawae Pn1 isolated from a soybean field in the mid- 53 2000s in Illinois, U.S.A. (ATCC SD 5833; Federal Register 76(22), 5808, February 2, 2011; e.g. Clariva™ PN from Syngenta Crop Protection, LLC, USA), Penicillium bilaiae (also called P. bilaii) strains ATCC 18309 (= ATCC 74319), ATCC 20851 and / or ATCC 22348 (=ATCC 74318) originally isolated from soil in Alberta, Canada (Fertilizer Res.39, 97-103, 1994; Can. J. Plant Sci.78(1), 91-102, 1998; US 5,026,417, WO 1995 / 017806; e.g. Jump Start®, Provide® fromNovozymes Biologicals BioAg Group, Canada), Reynoutria sachalinensis extract (EP 0307510 B1; e.g. Regalia® SC from Marrone BioInnovations, Davis, CA, USA or Milsana® from BioFa AG, Germany), Steinernema carpocapsae (e.g. Millenium® from BASF Agricultural Specialities Limited, UK), S. feltiae (e.g. Nemashield® from BioWorks, Inc., USA; Nemasys® from BASFAgricultural Specialities Limited, UK), Streptomyces microflavus NRRL B-50550 (WO2014 / 124369; Bayer CropScience, Germany), Trichoderma asperelloides JM41R isolated in South Africa (NRRL 50759; also referred to as T. fertile; e.g. Trichoplus® from BASF Agricultural Specialities (Pty) Ltd., South Africa), T. harzianum T-22 also called KRL-AG2 (ATCC 20847; BioControl 57, 687-696, 2012; e.g. Plantshield® from BioWorks Inc., USA or SabrEx™ fromAdvanced Biological Marketing Inc., Van Wert, OH, USA).According to the invention, the solid material (dry matter) of the biopesticides (with the exception of oils e.g. Neem oil) are considered as active components (e.g. to be obtained after drying or evaporation of the extraction or suspension medium in case of liquid formulations of the microbial pesticides).In accordance with the invention, the weight ratios and percentages used herein for a biologicalextract e.g. Quillay extract are based on the total weight of the dry content (solid material) of the respective extract(s). The total weight ratios of compositions comprising at least one microbial pesticide in the form of viable microbial cells including dormant forms, can be determined using the amount of CFU ofthe respective microorganism to calculate the total weight of the respective active component withthe following equation that 1x1010CFU equals one gram of total weight of the respective active component. Colony forming unit is measure of viable microbial cells, in particular fungal and bacterial cells. In addition, here “CFU” may also be understood as the number of (juvenile) individual nematodes in case of (entomopathogenic) nematode biopesticides, e.g. Steinernemafeltiae.When mixtures comprising microbial pesticides are employed in crop protection, the application rates range from 1x106to 5x1016(or more) CFU / ha, preferably from 1x108to 1x1013CFU / ha, and even more preferably from 1x109to 5x1015CFU / ha and in particular from 1x1012to 5x1014CFU / ha. In the case of nematodes as microbial pesticides (e.g. Steinernema feltiae), theapplication rates regularly range from 1x105 to 1x1012 (or more), preferably from 1x108 to 1x1011,more preferably from 5x108to 1x1010individuals (e.g. in the form of eggs, juvenile or any other live stages, preferably in an infetive juvenile stage) per ha. 54 When mixtures comprising microbial pesticides are employed in seed treatment, the application rates generally range from 1x106to 1x1012(or more) CFU / seed, preferably from 1x106to 1x109CFU / seed. Furthermore, the application rates with respect to seed treatment generally range from 1x107to 1x1014(or more) CFU per 100 kg of seed, preferably from 1x109to 1x1012CFU per 100kg of seed.Formulations The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of the invention or a mixture thereof.An agrochemical composition comprises a pesticidally effective amount of a compound of theinvention or a mixture thereof. The compounds of the invention or the mixtures thereof can be converted into customary types of agro-chemical compositions, e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types aresuspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO,ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials e.g. seeds (e.g. GF). These and further composition types are defined in the “Catalogue of pesticideformulation types and international coding system”, Technical Monograph No. 2, 6th Ed. May2008, CropLife International. The compositions are prepared in a known manner, e.g. described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.Examples for suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants,dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.Suitable solvents and liquid carriers are water and organic solvents, e.g. mineral oil fractions ofmedium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; hydrocarbons, e.g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fattyacids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; andmixtures thereof. Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, CaSO4, MgSO4, MgO; 55 polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. (NH4)2SO4, (NH4)3PO4, NH4NO3, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof. Suitable surfactants are surface-active compounds, e.g. anionic, cationic, nonionic and am-photeric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants canbe used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective col-loid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1: Emulsifiers & Detergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International or North American Ed.). Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates,phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates,diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples ofsulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylatedalcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates. Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples ofalkoxylates are compounds e.g. alcohols, alkylphenols, amines, amides, arylphenols, fatty acidsor fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N- substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-basedsurfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters oralkylpolyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate. Suitable cationic surfactants are quaternary surfactants, e.g. quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphotericsurfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of theA-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A- B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines, orpolyethyleneamines.Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the invention on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further 56 examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5. Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.Suitable bactericides are bronopol and isothiazolinone derivatives e.g. alkylisothiazolinones andbenzisothiazolinones. Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea, and glycerin. Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids. Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, ironhexacyanoferrate) and organic colorants (e.g. alizarin-, azo-, and phthalocyanine colorants). Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers. Examples for composition types and their preparation are:i) Water-soluble concentrates (SL, LS)10-60 wt% of a compound I according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and / or in a water-soluble solvent (e.g. alcohols) up to 100 wt%. The active substance dissolves upon dilution with water.ii) Dispersible concentrates (DC)5-25 wt% of a compound I according to the invention and 1-10 wt% dispersant (e.g.polyvinylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion. iii) Emulsifiable concentrates (EC) 15-70 wt% of a compound I according to the invention and 5-10 wt% emulsifiers (e.g. calciumdodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). Dilution with water gives an emulsion.iv) Emulsions (EW, EO, ES)5-40 wt% of a compound I according to the invention and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insolubleorganic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into up to 100 wt% waterby means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.v) Suspensions (SC, OD, FS)In an agitated ball mill, 20-60 wt% of a compound I according to the invention are comminutedwith addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcoholethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active sub-stance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added. 57vi) Water-dispersible granules and water-soluble granules (WG, SG)50-80 wt% of a compound I according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e.g.extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution ofthe active substance. vii) Water-dispersible powders and water-soluble powders (WP, SP, WS) 50-80 wt% of a compound I according to the invention are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcoholethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stabledispersion or solution of the active substance. viii) Gel (GW, GF) In an agitated ball mill, 5-25 wt% of a compound I according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g.carboxymethylcellulose) and up to 100 wt% water to give a fine suspension of the activesubstance. Dilution with water gives a stable suspension of the active substance. ix) Microemulsion (ME) 5-20 wt% of a compound I according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alcoholethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h toproduce spontaneously a thermodynamically stable microemulsion. x) Microcapsules (CS) An oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g.methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueoussolution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. di-phenylme-thene-4,4’-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g.polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of a polyurea microcapsule. The monomers amount to 1-10 wt%. The wt% relate to the total CS composition.xi) Dustable powders (DP, DS)1-10 wt% of a compound I according to the invention are ground finely and mixed intimately withup to 100 wt% solid carrier, e.g. finely divided kaolin.xii) Granules (GR, FG) 58 0.5-30 wt% of a compound I according to the invention is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed. xiii) Ultra-low volume liquids (UL)1-50 wt% of a compound I according to the invention are dissolved in up to 100 wt% organicsolvent, e.g. aromatic hydrocarbon. The composition types i) to xi) may optionally comprise further auxiliaries, e.g. 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.The agrochemical compositions generally comprise between 0.01 and 95%, preferably be-tween0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum). Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides (e.g.herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the activesubstances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1. The user applies the composition according to the invention usually from a predosage device, aknapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemicalcomposition is made up with water, buffer, and / or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to- use spray liquor are applied per hectare of agricultural useful area.According to one embodiment, individual components of the composition of the invention e.g.parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate. In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e.g. components comprising compounds of theinvention and / or mixing partners as defined above, may be mixed by the user in a spray tank andfurther auxiliaries and additives may be added. In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e.g. components comprising compounds of the invention and / or mixing partners as defined above, can be applied jointly (e.g. after tank mix) orconsecutively.Application methods 59 The compounds of the invention are suitable for use in protecting crops, plants, plant propagation materials, e.g. seeds, or soil or water, in which the plants are growing, from attack or infestation by animal pests. Therefore, the invention also relates to a plant protection method, which comprises contacting crops, plants, plant propagation materials, e.g. seeds, or soil or water, inwhich the plants are growing, to be protected from attack or infestation by animal pests, with apesticidally effective amount of a compound of the invention. The compounds of the invention are also suitable for use in combatting or controlling animal pests. Therefore, the invention also relates to a method of combating or controlling animal pests, which comprises contacting the animal pests, their habitat, breeding ground, or food supply, or thecrops, plants, plant propagation materials, e.g. seeds, or soil, or the area, material or environmentin which the animal pests are growing or may grow, with a pesticidally effective amount of a compound of the invention. The compounds of the invention are effective through both contact and ingestion. Further-more, the compounds of the invention can be applied to any and all developmental stages, e.g. egg,larva, pupa, and adult.The compounds of the invention can be applied as such or in form of compositions comprising them as defined above. Furthermore, the compounds of the invention can be applied together with a mixing partner or in form of compositions comprising said mixtures. The components of said mixture can be applied simultaneously, jointly or separately, or in succession, that isimmediately one after another and thereby creating the mixture “in situ” on the desired location,e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures. The application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, e.g. seeds, soil, or the area, material or environment by the pests.Suitable application methods include i.a. soil treatment, seed treatment, in furrow application, andfoliar application. Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection. Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting. In furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrowwith seeds, applying the pesticidally active compound to the furrow, and closing the furrow. Foliarapplication refers to the application of the pesticidally active compound to plant foliage, e.g. through spray equipment. For foliar applications, it can be advantageous to modify the behavior of the pests by use of pheromones in combination with the compounds of the invention. Suitable pheromones for specific crops and pests are known and publicly available from databases ofpheromones and semiochemicals, e.g. http: / / www.pherobase.com.As used herein, the term "contacting" includes both direct contact (applying the com- pounds / compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds / compositions to the locus, i.e. habitat, 60 breeding ground, plant, seed, soil, area, material, or environment in which a pest is growing or may grow, of the animal pest or plant). The term “animal pest” includes arthropods, gastropods, and nematodes. Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects.Insects, which are of particular relevance for crops, are typically referred to as crop insect pests.The term "crop" refers to both, growing and harvested crops. The term “plant” includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize / sweet and field corn); beet, e.g. sugar beet, or fodder beet; fruits, e.g. pomes, stone fruits, or soft fruits, e.g. apples, pears, plums, peaches, nectarines,almonds, cherries, papayas, strawberries, raspberries, blackberries or gooseberries; leguminousplants, e.g. beans, lentils, peas, alfalfa, or soybeans; oil plants, e.g. rapeseed (oilseed rape), turnip rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts, or soybeans; cucurbits, e.g. squashes, pumpkins, cucumber or melons; fiber plants, e.g. cotton, flax, hemp, or jute; citrus fruit, e.g. oranges, lemons, grapefruits or mandarins; vegetables,e.g. eggplant, spinach, lettuce (e.g. iceberg lettuce), chicory, cabbage, asparagus, cabbages,carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers; lauraceous plants, e.g. avocados, cinnamon, or camphor; energy and raw material plants, e.g. corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines; hop; sweet leaf (Stevia); natural rubber plants or ornamental and forestry plants, shrubs,broad-leaved trees or evergreens, eucalyptus; turf; lawn; grass. Preferred plants include potatoessugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee, or sugar cane; fruits; vines; ornamentals; or vegetables, e.g. cucumbers, tomatoes, beans or squashes. The term "cultivated plants" is to be understood as including plants which have been modified bymutagenesis or genetic engineering in order to provide a new trait to a plant or to modify analready present trait. Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome. Targeted mutagenesis techniques frequently use oligonucleotides or proteins likeCRISPR / Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination. Typically, one or more genes are integrated into the genome of a plant in order to add a trait or improve a trait. These integrated genes are alsoreferred to as transgenes in the art, while plant comprising such transgenes are referred to astransgenic plants. The process of plant transformation usually produces several transformation events, which differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising 61 a specific “event”, which is referred to by a specific event name. Traits which have been introduced in plants or have been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought. Herbicide tolerance has been created by using mutagenesis as well as using genetic engineering.Plants which have been rendered tolerant to ALS inhibitor herbicides by conventional methods ofmutagenesis and breeding comprise plant varieties commercially available under the name Clearfield®. Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides andHPPD inhibitors, like isoxaflutole and mesotrione.Transgenes which have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621 and goxv247, for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, for tolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, for tolerance to sulfonylurea herbicides:zm-hra, csr1-2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csr1-2, for tolerance toHPPD inhibitor herbicides: hppdPF, W336 and avhppd-03. Transgenic corn events comprising herbicide tolerance genes are e.g., but not excluding others, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, HCEM485, VCO-Ø1981-5,676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6,MZIR098, T25, TC1507 and TC6275. Transgenic soybean events comprising herbicide tolerance genes are e.g., but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2,GU262, SYHTØH2, W62, W98, FG72 and CV127.Transgenic cotton events comprising herbicide tolerance genes are e.g., but not excluding others, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.Transgenic canola events comprising herbicide tolerance genes are e.g., but not excludingothers, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3. Insect resistance has mainly been created by transferring bacterial genes for insecticidal proteins to plants. Transgenes which have most frequently been used are toxin genes of Bacillus spec.and synthetic variants thereof, like cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2,cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), vip3Aa20. However, also genes of plant origin have been transferred to other plants. In particular genes coding for protease inhibitors, like CpTI and pinII. A further approach uses transgenes in order to 62 produce double stranded RNA in plants to target and downregulate in-sect genes. An example for such a transgene is dvsnf7. Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA are e.g., but not excluding others, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810,MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275,CBH-351, MIR162, DBT418 and MZIR098. Transgenic soybean events comprising genes for insecticidal proteins are e.g., but not excluding others, MON87701, MON87751 and DAS-81419. Transgenic cotton events comprising genes for insecticidal proteins are e.g., but not excludingothers, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808,42317, BNLA-601, Event1, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321. Increased yield has been created by increasing ear biomass using the transgene athb17, being present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32,being present in the soybean event MON87712.Cultivated plants comprising a modified oil content have been created by using the transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769. Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by usingthe transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb-4, comprised by soybean event IND-ØØ41Ø-5. Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combination of traits are herbicide tolerance to different groups of herbicides, insect tolerance to different kind of insects, in particulartolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several typesof insect resistance, herbicide tolerance with increased yield as well as a combination of herbicide tolerance and tolerance to abiotic conditions. Plants comprising singular or stacked traits as well as the genes and events providing these traits are known (http: / / www.isaaa.org / gmapprovaldatabase) and (http: / / cera-gmc.org / GMCropDatabase).Further information on specific events and methods to detect them can be found for canola events MS1, MS8, RF3, GT73, MON88302, KK179 in WO01 / 031042, WO01 / 041558, WO01 / 041558, WO02 / 036831, WO11 / 153186, WO13 / 003558, for cotton events MON1445, MON15985, MON531(MON15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210-23, COT67B,GHB614, T304-40, GHB119, MON88701, 81910 in WO02 / 034946, WO02 / 100163,WO02 / 100163, WO03 / 013224, WO04 / 072235, WO04 / 039986, WO05 / 103266, WO05 / 103266, WO06 / 128573, WO07 / 017186, WO08 / 122406, WO08 / 151780, WO12 / 134808, WO13 / 112527, for corn events GA21, MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 63 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, 4114, MON87427, DAS40278, MON87411, 33121, MON87403, MON87419 in WO98 / 044140, US02 / 102582, US03 / 126634, WO04 / 099447, WO04 / 011601, WO05 / 103301, WO05 / 061720, WO05 / 059103, WO06 / 098952, WO06 / 039376, US2007 / 292854, WO07 / 142840, WO07 / 140256, WO08 / 112019,WO09 / 103049, WO09 / 111263, WO10 / 077816, WO11 / 084621, WO11 / 062904, WO11 / 022469,WO13 / 169923, WO14 / 116854, WO15 / 053998, WO15 / 142571, for potato events E12, F10, J3, J55, V11, X17, Y9 in WO14 / 178910, WO14 / 178913, WO14 / 178941, WO14 / 179276, WO16 / 183445, WO17 / 062831, WO17 / 062825, for rice events LLRICE06, LLRICE601, LLRICE62 in WO00 / 026345, WO00 / 026356, WO00 / 026345 for soybean events H7-1,MON89788, A2704-12, A5547-127, DP305423, DP356043, MON87701, MON87769, CV127,MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419, DAS81419 x DAS44406-6, MON87751 in WO04 / 074492, WO06 / 130436, WO06 / 108674, WO06 / 108675, WO08 / 054747, WO08 / 002872, WO09 / 064652, WO09 / 102873, WO10 / 080829, WO10 / 037016, WO11 / 066384, WO11 / 034704, WO12 / 051199, WO12 / 082548, WO13 / 016527, WO13 / 016516,WO14 / 201235.The use of compositions according to the invention on cultivated plants may result in effects which are specific to a cultivated plant comprising a certain gene or event. These effects may comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigor, early or delayed ripening, cold orheat tolerance as well as changed amino acid or fatty acid spectrum or content.It has been found that the pesticidal activity of the compounds of the invention may be enhanced by the insecticidal trait of a modified plant. Furthermore, it has been found that the compounds of the invention are suitable for preventing insects to become resistant to the insecticidal trait or for combating pests, which already have become resistant to the insecticidal trait of a modified plant.Moreover, the compounds of the invention are suitable for combating pests, against which theinsecticidal trait is not effective, so that a complementary insecticidal activity can advantageously be used. The term "plant propagation material" refers to all the generative parts of the plant e.g. seeds and vegetative plant material e.g. cuttings and tubers (e.g. potatoes), which can be used for themultiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots,sprouts and other parts of plants. Seedlings and young plants, which are to be trans-planted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.The term “seed” embraces seeds and plant propagules of all kinds including but not limited to trueseeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds. 64 In general, "pesticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the variouscompounds / compositions used in the invention. A pesticidally effective amount of thecompositions will also vary according to the prevailing conditions e.g. desired pesticidal effect and duration, weather, target species, locus, mode of application. In the case of soil treatment, in furrow application or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from0.001 to 20 g per 100 m2.For use in treating crop plants, e.g. by foliar application, the rate of application of the active ingredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to40 g per hectare, or 40 to 50 g per hectare.The compounds of the invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling’s roots and shoots against soil pests and foliar insects. The invention therefore alsorelates to a method for the protection of seeds from insects, in particular from soil insects, and ofthe seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and / or after pregermination with a compound of the invention. The protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling’s shoots from piercing and sucking insects, chewing insects andnematodes.The term “seed treatment” comprises e.g. seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in-furrow application methods. Preferably, the seed treatment application of the active compound is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.The invention also comprises seeds coated with or containing the active compound. The term"coated with and / or containing" generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.Suitable seed is e.g. seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, e.g.seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, 65 tomatoes, leeks, pumpkin / squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants e.g. potatoes, sugar cane, tobacco, grapes, petunias, geranium / pelargoniums, pansies and impatiens. In addition, the active compound may also be used for the treatment of seeds from plants, whichhave been modified by mutagenisis or genetic engineering, and which e.g. tolerate the action ofherbicides or fungicides or insecticides. Conventional seed treatment formulations include e.g. flowable concentrates FS, solutions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF.These formulations can be applied to the seed diluted or undiluted. Application to the seeds iscarried out before sowing, either directly on the seeds or after having pregerminated the latter. Preferably, the formulations are applied such that germination is not included. The active substance concentrations in ready-to-use formulations, which may be obtained after two-to-tenfold dilution, are preferably from 0.01 to 60% by weight, more preferably from 0.1 to40% by weight.In a preferred embodiment a FS formulation is used for seed treatment. Typically, a FS formulation may comprise 1-800 g / l of active ingredient, 1-200 g / l Surfactant, 0 to 200 g / l anti- freezing agent, 0 to 400 g / l of binder, 0 to 200 g / l of a pigment and up to 1 liter of a solvent, preferably water.Especially preferred FS formulations of the compounds of the invention for seed treatment usuallycomprise from 0.1 to 80% by weight (1 to 800 g / l) of the active ingredient, from 0.1 to 20% by weight (1 to 200 g / l) of at least one surfactant, e.g.0.05 to 5% by weight of a wetter and from 0.5 to 15% by weight of a dispersing agent, up to 20% by weight, e.g. from 5 to 20% of an anti-freeze agent, from 0 to 15% by weight, e.g.1 to 15% by weight of a pigment and / or a dye, from 0 to 40%by weight, e.g. 1 to 40% by weight of a binder (sticker / adhesion agent), optionally up to 5% byweight, e.g. from 0.1 to 5% by weight of a thickener, optionally from 0.1 to 2% of an anti-foam agent, and optionally a preservative e.g. a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1% by weight and a filler / vehicle up to 100% by weight. In the treatment of seed, the application rates of the compounds of the invention are generallyfrom 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, morepreferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed. The invention therefore also relates to seed comprising a compound of the invention, or an agriculturally useful salt thereof, as defined herein. The amount of the compound of the inventionor the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed,preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops e.g. lettuce the rate can be higher. 66 The compounds of the invention may also be used for improving the health of a plant. Therefore, the invention also relates to a method for improving plant health by treating a plant, plant propagation material and / or the locus where the plant is growing or is to grow with an effective and non-phytotoxic amount of a compound of the invention.As used herein “an effective and non-phytotoxic amount” means that the compound is used in aquantity which allows to obtain the desired effect but which does not give rise to any phytotoxic symptom on the treated plant or on the plant grown from the treated propagule or treated soil. "Plant health" is defined as a condition of the plant and / or its products which is determined by several aspects alone or in combination with each other e.g. yield (e.g. increased biomass and / orincreased content of valuable ingredients), quality (e.g. improved content or composition ofcertain ingredients or shelf life), plant vigour (e.g. improved plant growth and / or greener leaves (“greening effect”), tolerance to abiotic (e.g. drought) and / or biotic stress (e.g. disease) and production efficiency (e.g., harvesting efficiency, processability). The above identified indicators for the health condition of a plant may be interdependent and mayresult from each other. Each indicator is defined in the art and can be determined by methodsknown to a skilled person. The compounds of the invention are also suitable for use against non-crop insect pests. For use against said non-crop pests, compounds of the invention can be used as bait composition, gel,general insect spray, aerosol, as ultra-low volume application and bed net (impregnated orsurface applied). Furthermore, drenching and rodding methods can be used. As used herein, the term “non-crop insect pest” refers to pests, which are particularly relevant for non-crop targets, e.g. ants, termites, wasps, flies, ticks, mosquitoes, bed bugs, crickets, or cockroaches.The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). The bait employed in thecomposition is a product, which is sufficiently attractive to incite insects e.g. ants, termites, wasps, flies, mosquitoes, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are preferably chosen from animal and / or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils ofanimal and / or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose,lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are known (http: / / www.pherobase.com).For use in bait compositions, the typical content of active ingredient is from 0.001 wt% to 15 wt%,desirably from 0.001 wt% to 5 wt% of active compound. Formulations of the compounds of the invention as aerosols (e.g in spray cans), oil sprays or pump sprays are highly suitable for professional or non-professional users for controlling pests 67 e.g. flies, fleas, ticks, bed bugs, mosquitoes or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents, furthermore auxiliaries e.g. emulsifiers, perfume oils, if appropriate stabilizers, and, if required, propellants. The oil spray formulations differ from the aerosol recipes in that no propellants are used.For use in spray compositions, the content of active ingredient is from 0.001 to 80 wt%, preferablyfrom 0.01 to 50 wt% and most preferably from 0.01 to 15 wt%. The compounds of the invention and its respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellowfever, lymphatic filariasis, and leishmaniasis) with compounds of the invention and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprisea mixture including the insecticide, optionally a repellent and at least one binder.The compounds of the invention and its compositions can be used for protecting wooden materials e.g. trees, board fences, sleepers, frames, artistic artifacts, etc. and buildings, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants, termites and / or wood or textile destroying beetles, and for controlling ants and termites fromdoing harm to crops or human beings (e.g. when the pests invade into houses and public facilitiesor nest in yards, orchards or parks). Customary application rates in the protection of materials are, e.g., from 0.001 g to 2000 g or from 0.01 g to 1000 g of active compound per m2treated material, desirably from 0.1 g to 50 g per m2. Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to95 wt%, preferably from 0.1 to 45 wt%, and more preferably from 1 to 25 wt% of at least onerepellent and / or insecticide. Digital application The compounds of the invention and the compositions containing them may be applied incombination with, or by utilizing smart agricultural technologies, such as precision agriculture,remote and proximate imaging and image recognition, or smart agricultural site management programs. These smart agricultural technologies typically include models, e.g. computer pro- grams, that support the user by considering information from a wide variety of sources to increase the quality and yield of harvested material, reduce damage by pests including the prediction ofpest pressure and smart application of crop protection products, secure environ-mentalprotection, support quick and reliable agronomic decision making, reduce usage of fertilizers and crop protection products, reduce product residues in consumables increase spatial and temporal precision of agronomical measures, automate processes, and enable traceability of measures. 68 Commercially available systems which include agronomic models are e.g. FieldScripts™ from The Climate Corporation, Xarvio™ from BASF, AGLogic™ from John Deere, etc. Information input for these models include but is not limited to soil data, information on the plants that are currently growing or that may grow at the area of interest including crop plants and / orunwanted vegetation, weather information, information on the location of the area and directlyderivable information thereof, information on pest pressure, information on beneficial organisms, and / or historic information of any of the aforementioned. The information usable for precision agriculture may be based on input by at least one user, be accessible from external data sources and databases, or be based on sensor data. Data sourcestypically includes proximate-detection systems like soil-borne sensors and remote sensing asmay be achieved by imaging with unmanned airborne vehicles like drones, or satellites. Sensors may be included in an Internet-of-Things system and may be directly or indirectly connected to the processing unit, e.g. via a wireless network and / or cloud applications. The information is typically taken into account by at least one processing unit and used to provide recommendationsand generate control signals.Typical technologies that are used in smart agricultural technologies include self-steering ro-bots (such as tractors, harvesters, drones), artificial intelligence (e.g. machine learning), imaging technologies (e.g. image segmentation technologies), big data analysis, and model generation, cloud computing, and machine-to-machine communication.Precision agriculture such as precision farming is characterized by spatially and / or temporallyresolved, targeted application of active ingredients like pesticides, plant-growth-regulators, fertilizers, and / or water including the variation of application rates over the agronomic site, zone or spot application, and of the spatially and / or temporally resolved, targeted planting or seeding of desired plant propagation material to an agronomic site. Precision farming typically includesthe use of geo-positioning technologies like GPS for gaining information on the location andboundaries of the area of interest, the utilized application equipment, sensing equipment and recorded data, and to control the actions of farm vehicles such as spraying. By combining geo- positioning data with (digital) maps, it is possible to (semi)-automate agricultural measures at the site of interest, e.g. by using (semi)-autonomous spraying or seeding equipment.Precision farming may typically include the application of smart spraying equipment, e.g. spotspraying, and precision spraying at a farm, e.g. by irrigation systems, tractors, robots, helicopters, airplanes, unmanned aerial vehicles, such as drones. Such equipment usually includes input sensors (such as e.g. a camera) and a processing unit configured to analyze the input data and configured to provide a recommendation or decision based on the analysis of the input data toapply the compounds of the invention or compositions comprising them to the agronomic site,e.g. the soil, the crop plants, or to control pests in a specific and precise manner. For example, pests may be detected, identified, and / or classified from imagery acquired by a camera. Such identification and / classification can make use of image processing algorithms, which may utilize 69 artificial intelligence (e.g. machine learning algorithms), or decision trees. In this manner, the compounds or compositions described herein can be applied only at the required location, point in time and dose rate.PestsThe compounds of the invention are especially suitable for efficiently combating animal pests e.g. arthropods, gastropods and nematodes including: insects from the order of Lepidoptera, e.g. Achroia grisella, Acleris spp. e.g. A. fimbriana, A. gloverana, A. variana; Acrolepiopsis assectella, Acronicta major, Adoxophyes spp. e.g. A.cyrtosema, A. orana; Aedia leucomelas, Agrotis spp. e.g. A. exclamationis, A. fucosa, A. ipsilon,A. orthogoma, A. segetum, A. subterranea; Alabama argillacea, Aleurodicus dispersus, Alsophila pometaria, Ampelophaga rubiginosa, Amyelois transitella, Anacampsis sarcitella, Anagasta kuehniella, Anarsia lineatella, Anisota senatoria, Antheraea pernyi, Anticarsia (=Thermesia) spp. e.g. A. gemmatalis; Apamea spp., Aproaerema modicella, Archips spp. e.g. A. argyrospila, A.fuscocupreanus, A. rosana, A. xyloseanus; Argyresthia conjugella, Argyroploce spp.,Argyrotaenia spp. e.g. A. velutinana; Athetis mindara, Austroasca viridigrisea, Autographa gamma, Autographa nigrisigna, Barathra brassicae, Bedellia spp., Bonagota salubricola, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp. e.g. C. murinana, C. podana; Cactoblastis cactorum, Cadra cautella, Calingo braziliensis, Caloptilistheivora, Capua reticulana, Carposina spp. e.g. C. niponensis, C. sasakii; Cephus spp.,Chaetocnema aridula, Cheimatobia brumata, Chilo spp. e.g. C. Indicus, C. suppressalis, C. partellus; Choreutis pariana, Choristoneura spp. e.g. C. conflictana, C. fumiferana, C. longicellana, C. murinana, C. occidentalis, C. rosaceana; Chrysodeixis (=Pseudoplusia) spp., e.g. C. eriosoma, C. includens; Cirphis unipuncta, Clysia ambiguella, Cnaphalocerus spp.,Cnaphalocrocis medinalis, Cnephasia spp., Cochylis hospes, Coleophora spp., Coliaseurytheme, Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Corcyra cephalonica, Crambus caliginosellus, Crambus teterrellus, Crocidosema (=Epinotia) aporema, Cydalima (=Diaphania) perspectalis, Cydia (=Carpocapsa) spp., e.g. C. pomonella, C. latiferreana; Dalaca noctuides, Datana integerrima, Dasychira pinicola, Dendrolimus spp., e.g. D. pini, D. spectabilis,D. sibiricus; Desmia funeralis, Diaphania spp., e.g. D. nitidalis, D. hyalinata; Diatraeagrandiosella, Diatraea saccharalis, Diphthera festiva, Earias spp. e.g. E. insulana, E. vittella; Ecdytolopha aurantianu, Egira (=Xylomyges) curialis, Elasmopalpus lignosellus, Eldana saccharina, Endopiza viteana, Enno-mos subsignaria, Eoreuma loftini, Ephestia spp., e.g. E. cautella, E. elutella, E. kuehniella; Epinotia aporema, Epiphyas postvittana, Erannis tiliaria,Erionota thrax, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis chrysorrhoea, Euxoaspp., Evetria bouliana, Faronta albilinea, Feltia spp. e.g. F. subterranean; Galleria mellonella, Gracillaria spp., Grapholita spp. e.g. G. funebrana, G. molesta, G. inopinata; Halysidota spp., Harrisina americana, Hedylepta spp., Helicoverpa spp. e.g. H. armigera (=Heliothis armigera), H. 70 zea (=Heliothis zea); Heliothis spp. e.g. H. assulta, H. subflexa, H. virescens; Hellula spp. e.g. H. undalis, H. rogatalis; Helocoverpa gelotopoeon, Hemileuca oliviae, Herpetogramma licarsisalis, Hibernia defoliaria, Hofmannophila pseudospretella, Homoeosoma electellum, Homona magnanima, Hypena scabra, Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus,Kakivoria flavofasciata, Keiferia lycopersicella, Lambdina fiscellaria fiscellaria, Lambdinafiscellaria lugubrosa, Lamprosema indicata, Laspeyresia molesta, Leguminivora glycinivorella, Lerodea eufala, Leucinodes orbonalis, Leucoma salicis, Leucoptera spp. e.g. L. coffeella, L. scitella; Leuminivora lycinivorella, Lithocolletis blancardella, Lithophane antennata, Llattia octo (=Amyna axis), Lobesia botrana, Lophocampa spp., Loxagrotis albicosta, Loxostege spp. e.g. L.sticticalis, L. cereralis; Lymantria spp., e.g. L. dispar, L. monacha; Lyonetia clerkella, Lyonetiaprunifoliella, Malacosoma spp., e.g. M. americanum, M. californicum, M. constrictum, M. neu- stria; Mamestra spp., e.g. M. brassicae, M. configurata; Mamstra brassicae, Manduca spp. e.g. M. quinquemaculata, M. sexta; Marasmia spp, Marmara spp., Maruca testulalis, Megalopyge lanata, Melanchra picta, Melanitis leda, Mocis spp., e.g. M. lapites, M. repanda; Mocis latipes,Monochroa fragariae, Mythimna separata, Nemapogon cloacella, Neoleucinodes elegantalis,Nepytia spp., Nymphula spp., Oiketicus spp., Omiodes indicata, Omphisa anastomosalis, Operophtera brumata, Orgyia pseudotsugata, Oria spp., Orthaga thyrisalis, Ostrinia spp. e.g. O. nubilalis; Oulema oryzae, Paleacrita vernata, Panolis flammea, Parnara spp., Papaipema nebris, Papilio cresphontes, Paramyelois transitella, Paranthrene regalis, Paysandisia archon,Pectinophora spp. e.g. P. gossypiella; Peridroma saucia, Perileucoptera spp., e.g. P. coffeella;Phalera bucephala, Phryganidia californica, Phthorimaea spp. e.g. P. operculella; Phyllocnistis citrella, Phyllonorycter spp. e.g. P. blancardella, P. crataegella, P. issikii, P. ringoniella; Pieris spp. e.g. P. brassicae, P. rapae, P. napi; Pilocrocis tripunctata, Plathypena scabra, Platynota spp. e.g. P. flavedana, P. idaeusalis, P. stultana; Platyptilia carduidactyla, Plebejus argus, Plo-diainterpunctella, Plusia spp, Plutella maculipennis, Plutella xylostella, Pontia protodica, Prays spp.,Prodenia spp., Proxenus lepigone, Pseudaletia spp. e.g. P. sequax, P. unipuncta; Pyrausta nubilalis, Rachiplusia nu, Richia albicosta, Rhizobius ventralis, Rhyacionia frustrana, Sabulodes aegrotata, Schizura concinna, Schoenobius spp., Schreckensteinia festaliella, Scirpophaga spp. e.g. S. incertulas, S. innotata; Scotia segetum, Sesamia spp. e.g. S. inferens, Seudyra subflava,Sitotroga cerealella, Sparganothis pilleriana, Spilonota lechriaspis, S. ocelli-na, Spodoptera(=Lamphygma) spp. e.g. S. cosmoides, S. eridania, S. exigua, S. frugiperda, S. latisfascia, S. littoralis, S. litura, S. omithogalli; Stigmella spp., Stomopteryx subsecivella, Strymon bazochii, Sylepta derogata, Synanthedon spp. e.g. S. exitiosa, Tecia solanivora, Telehin licus, Thaumatopoea pityocampa, Thaumatotibia (=Cryptophlebia) leucotreta, Thaumetopoeapityocampa, Thecla spp., Theresimima ampelophaga, Thyrinteina spp, Tildenia inconspicuella,Tinea spp. e.g. T. cloacella, T. pellionella; Tineola bisselliella, Tortrix spp. e.g. T. viridana; Trichophaga tapetzella, Trichoplusia spp. e.g. T. ni; Tuta (=Scrobipalpula) absoluta, Udea spp. e.g. U. rubigalis, U. rubigalis; Virachola spp., Yponomeuta padella, and Zeiraphera canadensis; 71 insects from the order of Coleoptera, e.g. Acalymma vittatum, Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agrilus spp. e.g. A. anxius, A. planipennis, A. sinuatus; Agriotes spp. e.g. A. fuscicollis, A. lineatus, A. obscurus; Alphitobius diaperinus, Amphimallus solstitialis, Anisandrus dispar, Anisoplia austriaca, Anobium punctatum, Anomala corpulenta, Anomalarufocuprea, Anoplophora spp. e.g. A. glabripennis; Anthonomus spp. e.g. A. eugenii, A. grandis,A. pomorum; Anthrenus spp., Aphthona euphoridae, Apion spp., Apogonia spp., Athous haemorrhoidalis, Atomaria spp. e.g. A. linearis; Attagenus spp., Aulacophora femoralis, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. e.g. B. lentis, B. pisorum, B. rufimanus; Byctiscus betulae, Callidiellum rufipenne, Callopistria floridensis,Callosobruchus chinensis, Cameraria ohridella, Cassida nebulosa, Cerotoma trifurcata, Cetoniaaurata, Ceuthorhynchus spp. e.g. C. assimilis, C. napi; Chaetocnema tibialis, Cleonus mendicus, Conoderus spp. e.g. C. vespertinus; Conotrachelus nenuphar, Cosmopolites spp., Costelytra zealandica, Crioceris asparagi, Cryptolestes ferrugineus, Cryptorhynchus lapathi, Ctenicera spp. e.g. C. destructor; Curculio spp., Cylindrocopturus spp., Cyclocephala spp., Dac-tylispa balyi,Dectes texanus, Dermestes spp., Diabrotica spp. e.g. D. undecimpunctata, D. speciosa, D.longicornis, D. semipunctata, D. virgifera; Diaprepes abbreviates, Dichocrocis spp., Dicladispa armigera, Diloboderus abderus, Diocalandra frumenti (Diocalandra stigmaticollis), Enaphalodes rufulus, Epilachna spp. e.g. E. varivestis, E. vigintioctomaculata; Epitrix spp. e.g. E. hirtipennis, E. similaris; Eutheola humilis, Eutinobothrus brasiliensis, Faustinus cubae, Gibbium psylloides,Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Hylamorpha elegans, Hylobiusabietis, Hylotrupes bajulus, Hypera spp., e.g. H. brunneipennis, H. postica; Hypomeces squamosus, Hypothenemus spp., Ips typographus, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp. e.g. L. bilineata, L. melanopus; Leptinotarsa spp. e.g. L. decemlineata; Leptispa pygmaea, Limonius californi-cus, Lissorhoptrusoryzophilus, Lixus spp., Luperodes spp., Lyctus spp. e.g. L. bruneus; Liogenys fuscus,Macrodactylus spp. e.g. M. subspinosus; Maladera matrida, Megaplatypus mutates, Megascelis spp., Melanotus communis, Meligethes spp. e.g. M. aeneus; Melolontha spp. e.g. M. hippocastani, M. melolontha; Metamasius hemipterus, Microtheca spp., Migdolus spp. e.g. M. fryanus, Monochamus spp. e.g. M. alternatus; Naupactus xanthographus, Niptus hololeucus,Oberia brevis, Oemona hirta, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagusoryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon spp. e.g. P. brassicae, P. cochleariae; Phoracantha recurva, Phyllobius pyri, Phyllopertha horticola, Phyllophaga spp. e.g. P. helleri; Phyllotreta spp. e.g. P. chrysocephala, P. nemorum, P. striolata, P. vittula; Phyllopertha horticola,Popillia japonica, Premnotrypes spp., Psacothea hilaris, Psylliodes chrysocephala, Prostephanustruncates, Psylliodes spp., Ptinus spp., Pulga saltona, Rhizopertha dominica, Rhynchophorus spp. e.g. R. billineatus, R. ferrugineus, R. palmarum, R. phoenicis, R. vulneratus; Saperda candida, Scolytus schevyrewi, Scyphophorus acupunctatus, Sitona lineatus, Sitophilus spp. e.g. 72 S. granaria, S. oryzae, S. zeamais; Sphenophorus spp. e.g. S. levis; Stegobium paniceum, Sternechus spp. e.g. S. subsignatus; Strophomorphus ctenotus, Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp. e.g. T. castaneum; Trogoderma spp., Tychius spp., Xylotrechus spp. e.g. X. pyrrhoderus; and, Zabrus spp. e.g. Z.tenebrioides;insects from the order of Diptera e.g. Aedes spp. e.g. A. aegypti, A. albopictus, A. vexans; Anastrepha ludens, Anopheles spp. e.g. A. albimanus, A. crucians, A. freeborni, A. gambiae, A. leucosphyrus, A. maculipennis, A. minimus, A. quadrimaculatus, A. sinensis; Bactrocera invadens, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata,Chrysomyia spp. e.g. C. bezziana, C. hominivorax, C. macellaria; Chrysops atlanticus, Chrysopsdiscalis, Chrysops silacea, Cochliomyia spp. e.g. C. hominivorax; Contarinia spp. e.g. C. sorghicola; Cordylobia anthropophaga, Culex spp. e.g. C. nigripalpus, C. pipiens, C. quinquefasciatus, C. tarsalis, C. tritaeniorhynchus; Culicoides furens, Culiseta inornata, Culiseta melanura, Cuterebra spp., Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Dasineuraoxycoccana, Delia spp. e.g. D. antique, D. coarctata, D. platura, D. radicum; Dermatobia hominis,Drosophila spp. e.g. D. suzukii, Fannia spp. e.g. F. canicularis; Gastraphilus spp. e.g. G. intestinalis; Geomyza tipunctata, Glossina spp. e.g. G. fuscipes, G. morsitans, G. palpalis, G. tachinoides; Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia spp. e.g. H. platura; Hypoderma spp. e.g. H. lineata; Hyppobosca spp., Hydrellia philippina, Leptoconopstorrens, Liriomyza spp. e.g. L. sativae, L. trifolii; Lucilia spp. e.g. L. caprina, L. cuprina, L. sericata;Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. e.g. M. destructor; Musca spp. e.g. M. autumnalis, M. domestica; Muscina stabulans, Oestrus spp. e.g. O. ovis; Opomyza florum, Oscinella spp. e.g. O. frit; Orseolia oryzae, Pegomya hysocyami, Phlebotomus argentipes, Phorbia spp. e.g. P. antiqua, P. brassicae, P. coarctata; Phytomyza gymnostoma, Prosimuliummixtum, Psila rosae, Psorophora columbiae, Psorophora discolor, Rhagoletis spp. e.g. R. cerasi,R. cingulate, R. indifferens, R. mendax, R. pomonella; Rivellia quadrifasciata, Sarcophaga spp. e.g. S. haemorrhoidalis; Simulium vittatum, Sitodiplosis mosellana, Stomoxys spp. e.g. S. calcitrans; Tabanus spp. e.g. T. atratus, T. bovinus, T. lineola, T. similis; Tannia spp., Thecodiplo- sis japonensis, Tipula oleracea, Tipula paludosa, Wohlfahrtia spp, and Zaprionus indianus;insects from the order of Thysanoptera e.g., Baliothrips biformis, Dichromothrips corbetti,Dichromothrips ssp., Echinothrips americanus, Enneothrips flavens, Frankliniella spp. e.g. F. fusca, F. occidentalis, F. tritici; Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Microcephalothrips abdominalis, Neohydatothrips samayunkur, Pezothrips kellyanus, Rhipiphorothrips cruentatus, Scirtothrips spp. e.g. S. citri, S. dorsalis, S. perseae;Stenchaetothrips spp, Taeniothrips cardamoni, Taeniothrips inconsequens, Thrips spp. e.g. T.imagines, T. hawaiiensis, T. oryzae, T. palmi, T. parvispinus, T. tabaci; insects from the order of Hemiptera e.g., Acizzia jamatonica, Acrosternum spp., e.g. A. hilare; Acyrthosipon spp., e.g. A. onobrychis, A. pisum; Adelges laricis, Adelges tsugae, Adelphocoris 73 spp., e.g. A. rapidus, A. superbus; Aeneolamia spp., Agonoscena spp., Aulacorthum solani, Aleurocanthus woglumi, Aleurodes spp., Aleurodicus disperses, Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anasa tristis, Antestiopsis spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphidula nasturtii, Aphis spp. e.g. A. craccivora, A. fabae, A. forbesi, A.gossypii, A. grossulariae, A. maidiradicis, A. pomi, A. sambuci, A. schneideri, A. spiraecola;Arboridia apicalis, Arilus critatus, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacaspis yasumatsui, Aulacorthum solani, Bactericera cockerelli (Paratrioza cockerelli), Bemisia spp. e.g. B. argentifolii, B. tabaci (Aleurodes tabaci); Blissus spp. e.g. B. leucopterus; Brachycaudus spp. e.g. B. cardui, B. helichrysi, B. persicae, B. prunicola; Brachycolus spp., Brachycorynella as-paragi, Brevicoryne brassicae, Cacopsylla spp. e.g. C. fulguralis, C. pyricola (Psylla piri);Calligypona marginata, Calocoris spp., Campylomma livida, Capitophorus horni, Carneocephala fulgida, Cavelerius spp., Ceraplastes spp., Ceratovacuna lanigera, Ceroplastes ceriferus, Cerosipha gossypii, Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Cimex spp. e.g. C. hemipterus, C.lectularius; Circulifer tenellus, Coccomytilus halli, Coccus spp. e.g. C. hesperidum, C.pseudomagnoliarum; Corythucha arcuata, Creontiades dilutus, Cryptomyzus ribis, Chrysomphalus aonidum, Cryptomyzus ribis, Ctenarytaina spatulata, Cyrtopeltis notatus, Dalbulus spp., Dasynus piperis, Dialeurodes spp. e.g. D. citrifolii; Dalbulus maidis, Diaphorina spp. e.g. D. citri; Diaspis spp. e.g. D. bromeliae; Dichelops furcatus, Diconocoris hewetti, Doralisspp., Dreyfusia nordmannianae, Dreyfusia piceae, Drosicha spp., Dysaphis spp. e.g. D.plantaginea, D. pyri, D. radicola; Dysaulacorthum pseudosolani, Dysdercus spp. e.g. D. cingulatus, D. intermedius; Dysmicoccus spp., Edessa spp., Geocoris spp., Empoasca spp. e.g. E. fabae, E. solana; Epidiaspis leperii, Eriosoma spp. e.g. E. lanigerum, E. pyricola; Erythroneura spp., Eurygaster spp. e.g. E. integriceps; Euscelis bilobatus, Euschistus spp. e.g. E. heros, E.impictiventris, E. servus; Fiorinia theae, Geococcus coffeae, Glycaspis brimblecombei,Halyomorpha spp. e.g. H. halys; Heliopeltis spp., Homalodisca vitripennis (=H. coagulata), Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lactucae, Icerya spp. e.g. I. purchase; Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lecanoideus floccissimus, Lepidosaphes spp. e.g. L. ulmi; Leptocorisa spp., Leptoglossus phyllopus, Lipaphiserysimi, Lygus spp. e.g. L. hesperus, L. lineolaris, L. praten-sis; Maconellicoccus hirsutus,Marchalina hellenica, Macropes excavatus, Macrosiphum spp. e.g. M. rosae, M. avenae, M. euphorbiae; Macrosteles quadrilineatus, Mahanarva fimbriolata, Megacopta cribraria, Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari, Melanocallis (=Tinocallis) caryaefoliae, Metcafiella spp., Metopolophium dirhodum, Monellia costalis, Mo-nelliopsis pecanis, Myzocalliscoryli, Murgantia spp., Myzus spp. e.g. M. ascalonicus, M. cerasi, M. nicotianae, M. persicae, M.varians; Nasonovia ribisnigri, Neotoxoptera formosana, Neomegalotomus spp, Nephotettix spp. e.g. N. malayanus, N. nigropictus, N. parvus, N. vires-cens; Nezara spp. e.g. N. viridula; Nilaparvata lugens, Nysius huttoni, Oebalus spp. e.g. O. pugnax; Oncometopia spp., Orthezia 74 praelonga, Oxycaraenus hyalinipennis, Parabemisia myricae, Parlatoria spp., Parthenolecanium spp. e.g. P. corni, P. persicae; Pemphigus spp. e.g. P. bursarius, P. populivenae; Peregrinus maidis, Perkinsiella saccharicida, Phenacoccus spp. e.g. P. aceris, P. gossypii; Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp. e.g. P. devastatrix, Piesma quadrata, Piezodorusspp. e.g. P. guildinii; Pinnaspis aspidistrae, Planococcus spp. e.g. P. citri, P. ficus; Prosapiabicincta, Protopulvinaria pyriformis, Psallus seriatus, Pseudacysta persea, Pseudaulacaspis pentagona, Pseudococcus spp. e.g. P. comstocki; Psylla spp. e.g. P. mali; Pteromalus spp., Pulvinaria amygdali, Pyrilla spp., Quadraspidiotus spp., e.g. Q. perniciosus; Quesada gigas, Rastrococcus spp., Reduvius senilis, Rhizoecus americanus, Rhodnius spp., Rhopalomyzusascalonicus, Rhopalosiphum spp. e.g. R. pseudobrassicas, R. insertum, R. maidis, R. padi;Sagatodes spp., Sahlbergella singularis, Saissetia spp., Sappaphis mala, Sappaphis mali, Scaptocoris spp., Scaphoideus titanus, Schizaphis graminum, Schizoneura lanuginosa, Scotinophora spp., Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Solubea insularis, Spissistilus festinus (=Stictocephala festina), Stephanitis nashi, Stephanitispyrioides, Stephanitis takeyai, Tenalaphara malayensis, Tetraleurodes perseae, Therioaphismaculate, Thyanta spp. e.g. T. accerra, T. perditor; Tibraca spp., Tomaspis spp., Toxoptera spp. e.g. T. aurantii; Trialeurodes spp. e.g. T. abutilonea, T. ricini, T. vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. e.g. U. citri, U. yanonensis; and Viteus vitifolii, Insects from the order Hymenoptera e.g. Acanthomyops interjectus, Athalia rosae, Atta spp. e.g.A. capiguara, A. cephalotes, A. cephalotes, A. laevigata, A. robusta, A. sexdens, A. texana,Bombus spp., Brachymyrmex spp., Camponotus spp. e.g. C. floridanus, C. pennsylvanicus, C. modoc; Cardiocondyla nuda, Chalibion sp, Crematogaster spp., Dasymutilla occidentalis, Diprion spp., Dolichovespula maculata, Dorymyrmex spp., Dryocosmus kuriphilus, Formica spp., Hoplocampa spp. e.g. H. minuta, H. testudinea; Iridomyrmex humilis, Lasius spp. e.g. L. niger,Linepithema humile, Liometopum spp., Leptocybe invasa, Monomorium spp. e.g. M. pharaonis,Monomorium, Nylandria fulva, Pachycondyla chinensis, Paratrechina longicornis, Paravespula spp., e.g. P. germanica, P. pennsylvanica, P. vulgaris; Pheidole spp. e.g. P. megacephala; Pogonomyrmex spp. e.g. P. barbatus, P. californicus, Polistes rubiginosa, Prenolepis impairs, Pseudomyrmex gracilis, Schelipron spp., Sirex cyaneus, Solenopsis spp. e.g. S. geminata,S.invicta, S. molesta, S. richteri, S. xyloni, Sphecius speciosus, Sphex spp., Tapinoma spp. e.g.T. melanocephalum, T. sessile; Tetramorium spp., e.g. T. caespitum, T. bicarinatum, Vespa spp., e.g. V. crabro; Vespula spp., e.g. V. squamosal; Wasmannia auropunctata, Xylocopa sp; Insects from the order Orthoptera e.g. Acheta domesticus, Calliptamus italicus, Chortoicetes terminifera, Ceuthophilus spp., Diastrammena asynamora, Dociostaurus maroccanus,Gryllotalpa spp. e.g. G. africana, G. gryllotalpa; Gryllus spp., Hieroglyphus daganensis,Kraussaria angulifera, Locusta spp. e.g. L. migratoria, L. pardalina; Melanoplus spp. e.g. M. bivittatus, M. femurrubrum, M. mexicanus, M. sanguinipes, M. spretus; Nomadacris 75 septemfasciata, Oedaleus senegalensis, Scapteriscus spp., Schistocerca spp. e.g. S. americana, S. gregaria, Stemopelmatus spp., Tachycines asynamorus, and Zonozerus variegatus; Pests from the Class Arachnida e.g. Acari,e.g. of the families Argasidae, Ixodidae and Sar- coptidae, e.g. Amblyomma spp. (e.g. A. americanum, A. variegatum, A. maculatum), Argas spp.e.g. A. persicu), Boophilus spp. e.g. B. annulatus, B. decoloratus, B. microplus, Dermacentor spp.e.g. D.silvarum, D. andersoni, D. variabilis, Hyalomma spp. e.g. H. truncatum, Ixodes spp. e.g. I. ricinus, I. rubicundus, I. scapularis, I. holocyclus, I. pacificus, Rhipicephalus sanguineus, Ornithodorus spp. e.g. O. moubata, O. hermsi, O. turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes spp. e.g. P. ovis, Rhipicephalus spp. e.g. R.sanguineus, R. appendiculatus, Rhipicephalus evertsi, Rhizoglyphus spp., Sarcoptes spp. e.g. S.Scabiei; and Family Eriophyidae including Aceria spp. e.g. A. sheldoni, A. anthocoptes, Acallitus spp., Aculops spp. e.g. A. lycopersici, A. pelekassi; Aculus spp. e.g. A. schlechtendali; Colomerus vitis, Epitrimerus pyri, Phyllocoptruta oleivora; Eriophytes ribis and Eriophyes spp. e.g. Eriophyes sheldoni; Family Tarsonemidae including Hemitarsonemus spp., Phytonemus pallidus andPolyphagotarsonemus latus, Stenotarsonemus spp. Steneotarsonemus spinki; FamilyTenuipalpidae including Brevipalpus spp. e.g. B. phoenicis; Family Tetranychidae including Eotetranychus spp., Eutetranychus spp., Oligonychus spp., Petrobia latens, Tetranychus spp. e.g. T. cinnabarinus, T. evansi, T. kanzawai, T, pacificus, T. phaseulus, T. telarius and T. urticae; Bryobia praetiosa; Panonychus spp. e.g. P. ulmi, P. citri; Metatetranychus spp. and Oligonychusspp. e.g. O. pratensis, O. perseae, Vasates lycopersici; Raoiella indica, Family Carpoglyphidaeincluding Carpoglyphus spp.; Penthaleidae spp. e.g. Halotydeus destructor; Family Demodicidae with species e.g. Demodex spp.; Family Trombicidea including Trombicula spp.; Family Macronyssidae including Ornothonyssus spp.; Family Pyemotidae including Pyemotes tritici; Tyrophagus putrescentiae; Family Acaridae includ-ing Acarus siro; Family Araneida includingLatrodectus mactans, Eratigena agrestis, Cheiracanthium sp, Lycosa sp Achaearaneatepidariorum and Loxosceles reclusa; Pests from the Phylum Nematoda, e.g. plant parasitic nematodes e.g. root-knot nematodes, Meloidogyne spp. e.g. M. hapla, M. incognita, M. javanica; cyst-forming nematodes, Globodera spp. e.g. G. rostochiensis; Heterodera spp. e.g. H. avenae, H. glycines, H. schachtii, H. trifolii;Seed gall nematodes, Anguina spp.; Stem and foliar nematodes, Aphelenchoides spp. e.g. A.besseyi; Sting nematodes, Belonolaimus spp. e.g. B. longicaudatus; Pine nematodes, Bursaphelenchus spp. e.g. B. lignicolus, B. xylophilus; Ring nematodes, Criconema spp., Criconemella spp. e.g. C. xenoplax and C. ornata; and, Criconemoides spp. e.g. Criconemoides informis; Mesocriconema spp.; Stem and bulb nematodes, Ditylenchus spp. e.g. D. destructor, D.dipsaci; Awl nematodes, Dolichodorus spp.; Spiral nematodes, Heliocotylenchus multicinctus;Sheath and sheathoid nematodes, Hemicycliophora spp. and Hemicriconemoides spp.; Hirshmanniella spp.; Lance nematodes, Hoploaimus spp.; False rootknot nematodes, Nacobbus spp.; Needle nematodes, Longidorus spp. e.g. L. elongatus; Lesion nematodes, Pratylenchus 76 spp. e.g. P. brachyurus, P. neglectus, P. penetrans, P. curvitatus, P. goodeyi; Burrowing nema- todes, Radopholus spp. e.g. R. similis; Rhadopholus spp.; Rhodopholus spp.; Reniform nematodes, Rotylenchus spp. e.g. R. robustus, R. reniformis; Scutellonema spp.; Stubby-root nematode, Trichodorus spp. e.g. T. obtusus, T. primitivus; Paratrichodorus spp. e.g. P. minor;Stunt nematodes, Tylenchorhynchus spp. e.g. T. claytoni, T. dubius; Citrus nematodes,Tylenchulus spp. e.g. T. semipenetrans; Dagger nematodes, Xiphinema spp.; and other plant parasitic nematode species; Insects from the order Blattodea e.g. Macrotermes spp. e.g. M. natalensis; Cornitermes cu- mulans, Procornitermes spp., Globitermes sulfureus, Neocapritermes spp. e.g. N. opacus, N.parvus; Odontotermes spp., Nasutitermes spp. e.g. N. corniger; Coptotermes spp. e.g. C. for-mosanus, C. gestroi, C. acinaciformis; Reticulitermes spp. e.g. R. hesperus, R. tibialis, R. speratus, R. flavipes, R. grassei, R. lucifugus, R. virginicus; Heterotermes spp. e.g. H. aureus, H. longiceps, H. tenuis; Cryptotermes spp. e.g. C. brevis, C. cavifrons; Incisitermes spp. e.g. I. minor, I. snyderi; Marginitermes hubbardi, Kalotermes flavicollis, Neotermes spp. e.g. N. cas-taneus,Zootermopsis spp. e.g. Z. angusticollis, Z. nevadensis, Mastotermes spp. e.g. M. dar-winiensis;Blatta spp. e.g. B. orientalis, B. lateralis; Blattella spp. e.g. B. asahinae, B. germanica; Rhyparobia maderae, Panchlora nivea, Periplaneta spp. e.g. P. americana, P. australasiae, P. brunnea, P. fuliginosa, P. japonica; Supella longipalpa, Parcoblatta pennsylvanica, Eurycotis floridana, Pycnoscelus surinamensis,Insects from the order Siphonoptera e.g. Cediopsylla simples, Ceratophyllus spp., Ctenoce-phalides spp. e.g. C. felis, C. canis, Xenopsylla cheopis, Pulex irritans, Trichodectes canis, Tunga penetrans, and Nosopsyllus fasciatus, Insects from the order Thysanura e.g. Lepisma saccharina, Ctenolepisma urbana, and Thermobia domestica,Pests from the class Chilopoda e.g. Geophilus spp., Scutigera spp. e.g. Scutigera coleoptrata;Pests from the class Diplopoda e.g. Blaniulus guttulatus, Julus spp., Narceus spp., Pests from the class Symphyla e.g. Scutigerella immaculata, Insects from the order Dermaptera, e.g. Forficula auricularia, Insects from the order Collembola, e.g. Onychiurus spp., e.g. Onychiurus armatus,Pests from the order Isopoda, e.g. Armadillidium vulgare, Oniscus asellus, Porcellio scaber,Insects from the order Phthiraptera, e.g. Damalinia spp., Pediculus spp. e.g. Pediculus hu-manus capitis, Pediculus humanus corporis, Pediculus humanus humanus; Pthirus pubis, Haematopinus spp. e.g. Haematopinus eurysternus, Haematopinus suis; Linognathus spp. e.g. Linognathus vituli; Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus,Trichodectes spp.,Further pest species which may be controlled by compounds I include: from the Phylum Mollusca, class Bivalvia, e.g., Dreissena spp.; class Gastropoda, e.g., Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea 77 canaliclata, Succinea spp.; from the class of the helminths, e.g., 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, Dracunculusmedinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis,Faciola spp., Haemonchus spp. e.g. Haemonchus contortus; Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuel- leborni, Strongyloides stercora lis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinellaspiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis,Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti. The compounds of the invention are particularly suitable for efficiently combating insects from the sub-order of Auchenorrhyncha, e.g. Amrasca biguttula, Empoasca spp., Nephotettix virescens, Sogatella furcifera, Mahanarva spp., Laodelphax striatellus, Nilapar-vatalugens, Diaphorina citri, Lycorma delicatula, Pentastiridus leporinus;Lepidoptera, e.g. Helicoverpa spp., Heliothis virescens, Lobesia botrana, Ostrinia nubilalis, Plutella xylostella, Pseudoplusia includens, Scirpophaga incertulas, Spodoptera spp., Trichoplusia ni, Tuta absoluta, Cnaphalocrocis medialis, Cydia pomonella, Chilo suppressalis, Anticarsia gemmatalis, Agrotis ipsilon, Chrysodeixis includens;True bugs, e.g. Lygus spp., Stink bugs such as Euschistus spp., Halyomorpha halys, Nezaraviridula, Piezodorus guildinii, Dichelops furcatus; Thrips, e.g. Frankliniella spp., Thrips spp., Dichromothrips corbettii; Aphids, e.g. Acyrthosiphon pisum, Aphis spp., Myzus persicae, Rhopalosiphum spp., Schi-zaphis graminum, Megoura viciae;Whiteflies, e.g. Trialeurodes vaporariorum, Bemisia spp.;Coleoptera, e.g. Phyllotreta spp., Melanotus spp., Meligethes aeneus, Leptinotarsa decimlineata, Ceutorhynchus spp., Diabrotica spp., Anthonomus grandis, Atomaria linearia, Agriotes spp., Epilachna spp.; Flies, e.g. Delia spp., Ceratitis capitate, Bactrocera spp., Liriomyza spp.;Coccoidea, e.g. Aonidiella aurantia, Ferrisia virgate;Anthropods of class Arachnida (Mites), e.g. Penthaleus major, Tetranychus spp.; Nematodes, e.g. Heterodera glycines, Meloidogyne sp., Pratylenchus spp., Caenorhabditis elegans.Animal healthThe compounds of the invention are suitable for use in treating or protecting animals against infestation or infection by parasites. Therefore, the invention also relates to the use of a compound of the invention for the manufacture of a medicament for the treatment or protection of animals 78 against infestation or infection by parasites. Furthermore, the invention relates to a method of treating or protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of the invention.The invention also relates to the non-therapeutic use of compounds of the invention for treatingor protecting animals against infestation and infection by parasites. Moreover, the invention relates to a non-therapeutic method of treating or protecting animals against infestation and infection by parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the invention.The compounds of the invention are further suitable for use in combating or controlling parasitesin and on animals. Furthermore, the invention relates to a method of combating or con-trolling parasites in and on animals, which comprises contacting the parasites with a parasitically effective amount of a compound of the invention. The invention also relates to the non-therapeutic use of compounds of the invention for con-trolling or combating parasites. Moreover, the invention relates to a non-therapeutic method ofcombating or controlling parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the invention. The compounds of the invention can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits). Furthermore, the compounds ofthe invention can be applied to any and all developmental stages.The compounds of the invention can be applied as such or in form of compositions comprising the compounds of the invention. The compounds of the invention can also be applied together with a mixing partner, which acts against pathogenic parasites, e.g. with synthetic coccidiosis compounds, polyetherantibiotics e.g.Amprolium, Robenidin, Toltrazuril, Monensin, Salinomycin, Maduramicin, Lasalocid, Narasin orSemduramicin, or with other mixing partners as defined above, or in form of compositions comprising said mixtures. The compounds of the invention and compositions comprising them can be applied orally, parenterally or topically, e.g. dermally. The compounds of the invention can be systemically ornon-systemically effective.The application can be carried out prophylactically, therapeutically or non-therapeutically. Furthermore, the application can be carried out preventively to places at which occurrence of the parasites is expected. As used herein, the term "contacting" includes both direct contact (applying the com-pounds / compositions directly on the parasite, including the application directly on the animal orexcluding the application directly on the animal, e.g. at its locus for the latter) and indirect contact (applying the compounds / compositions to the locus of the parasite). The contact of the parasite 79 through application to its locus is an example of a non-therapeutic use of the compounds of the invention. The term "locus" means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal.As used herein, the term “parasites” includes endo- and ectoparasites. In some embodiments ofthe invention, endoparasites can be preferred. In other embodiments, ectoparasites can be preferred. Infestations in warm-blooded animals and fish include lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas. The compounds of the invention are especially useful for combating parasites of the followingorders and species, respectively:fleas (Siphonaptera), e.g. Ctenocephalides felis, C. canis, Xenopsylla cheopis, Pulex irri-tans, Tunga penetrans, and Nosopsyllus fasciatus; cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, B. asahinae, Periplaneta americana, P. japonica, P. brunnea, P. fuligginosa, P. australasiae, and Blatta orientalis; flies, mosquitoes (Diptera), e.g. Aedes aegypti, A. albopictus,A. vexans, Anastrepha ludens, Anopheles maculipennis, A. crucians, A. albimanus, A. gambiae,A. freeborni, A. leucosphyrus, A. minimus, A. quadrimaculatus, Calliphora vicina, Chrysomya bezziana, C. hominivorax, C. macellaria, Chrysops discalis, C. silacea, C. atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, C. nigripalpus, C. quinquefasciatus, C. tarsalis, Culiseta inornata, C. melanura, Dermatobia hominis, Fanniacanicularis, Gasterophilus intestinalis, Glossina morsitans, G. palpalis, G. fuscipes, G.tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma line-ata, Leptoconops torrens, Lucilia caprina, L. cuprina, L. sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, M. stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, P. discolor, Prosimulium mixtum, Sarcophaga spp., S. haemorrhoidalis, Simulium vittatum,Stomoxys calcitrans, Tabanus bovinus, T. atratus, T. lineola, and T. similis; lice (Phthiraptera),e.g. Pediculus humanus capitis, P. humanus humanus, Pthirus pubis, Haematopinus eurysternus, H. suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus, and Solenopotes capillatus; ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, I. holocyclus, I. pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, D.variabilis, Amblyomma americanum, A. maculatum, Ornithodorus hermsi, O. turicata and parasiticmites (Mesostigmata), e.g. Ornithonyssus bacoti, Dermanyssus gallinae; Actinedida (Prostigmata) and Acaridida (Astigmata), e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demo-dex 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., Cytoditesspp., and Laminosioptes spp; Bugs (Het-eropterida): Cimex lectularius, C. hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp., and Arilus critatus; Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp.; 80 Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.; Roundworms Nematoda: Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp.; Rhabditida, e.g. Rhabditis spp.,Strongyloides spp., Helicephalobus spp.; Strongylida, e.g. Strongylus spp., Ancylostoma spp.,Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus, Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalusspp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp.,Angiostrongylus spp., Parelaphostrongylus spp., Aleurostrongylus abstrusus, and Dioctophyma renale; Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi; Camallanida, e.g. Dracunculus medinensis (guineaworm); Spirurida, e.g. Thelazia spp., Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilarispp.a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.; Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp.; Planarians (Plathelminthes): Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchissinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp., andNanocyetes spp.; Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllo-bothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp..The term “animal” includes warm-blooded animals (including humans) and fish. Preferred aremammals, e.g. cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals e.g. mink, chinchilla and raccoon, birds e.g. hens, geese, turkeys and ducks and fish e.g. fresh- and salt- water fish e.g. trout, carp and eels. Particularly preferred are domestic animals, e.g. dogs or cats.Generally, "parasiticidally effective amount" means the amount of active ingredient needed toachieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds / compositions used in the invention. A parasiticidally effective amount of thecompositions will also vary according to the prevailing conditions e.g. desired parasiticidal effectand duration, target species, mode of application. Generally, it is favorable to apply the compounds of the invention in total amounts of 0.5 mg / kg to 100 mg / kg per day, preferably 1 mg / kg to 50 mg / kg per day. 81 For oral administration to warm-blooded animals, the compounds I may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the compounds I may be ad-ministered to the animals in their drinking water. For oral administration, the dosage form chosen shouldprovide the animal with 0.01 mg / kg to 100 mg / kg of animal body weight per day of the compoundsI, preferably with 0.5 mg / kg to 100 mg / kg of animal body weight per day. Alternatively, the compounds I may be administered to animals parenterally, e.g., by intraruminal, intramuscular, intravenous or subcutaneous injection. The compounds I may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, thecompounds I may be formulated into an implant for subcutaneous administration. In addition thecompounds I may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg / kg to 100 mg / kg of animal body weight per day of the compounds I. The compounds I may also be applied topically to the animals in the form of dips, dusts, powders,collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the compounds I. In addition, the compounds I may be formulated as ear tags for animals, particularly quadrupeds e.g. cattle and sheep. Suitable preparations are:- Solutions e.g. oral solutions, concentrates for oral administration after dilution, solutions for useon the skin or in body cavities, pouring-on formulations, gels; - Emulsions and suspensions for oral or dermal administration; semi-solid preparations; - Formulations in which the active compound is processed in an ointment base or in an oil-in- water or water-in-oil emulsion base;- Solid preparations e.g. powders, premixes or concentrates, granules, pellets, tablets, boluses,capsules; aerosols and inhalants, and active compound-containing shaped articles. Compositions suitable for injection are prepared by dissolving the active ingredient in a suit-able solvent and optionally adding further auxiliaries e.g. acids, bases, buffer salts, preservatives, and solubilizers. Suitable auxiliaries for injection solutions are known in the art. The solutions arefiltered and filled sterile.Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary. Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.Solutions for use on the skin are prepared according to the state of the art and according to whatis described above for injection solutions, sterile procedures not being necessary. Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions 82 with sufficient thickener that a clear material having an ointment-like consistency results. Suitable thickeners are known in the art. Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically. Pour-on formulations are prepared by dis-solving,suspending or emulsifying the active compound in suitable skin-compatible solvents or solventmixtures. If appropriate, other auxiliaries e.g. colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added. Suitable such auxiliaries are known in the art. Emulsions can be administered orally, dermally or as injections. Emulsions are either of the water- in-oil type or of the oil-in-water type. They are prepared by dissolving the active com-pound eitherin the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the otherphase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries e.g. colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity- enhancing substances. Suitable hydrophobic phases (oils), suitable hydrophilic phases, suitable emulsifiers, and suitable further auxiliaries for emulsions are known in the art.Suspensions can be administered orally or topically / dermally. They are prepared by suspendingthe active compound in a suspending agent, if appropriate with addition of other auxiliaries e.g. wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers. Suitable suspending agents, and suitable other auxiliaries for suspensions including wetting agents are known in the art.Semi-solid preparations can be administered orally or topically / dermally. They differ from thesuspensions and emulsions described above only by their higher viscosity. For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form. Suitable auxiliaries for this purpose are known in the art.The compositions which can be used in the invention can comprise generally from about 0.001to 95% of the compound of the invention. Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80% by weight, preferably from 0.1 to 65% by weight, more preferably from 1 to 50% by weight, most preferably from 5 to 40% by weight.Preparations which are diluted before use contain the compounds acting against ectoparasites inconcentrations of 0.5 to 90% by weight, preferably of 1 to 50% by weight. Furthermore, the preparations comprise the compounds of formula I against endoparasites in concentrations of 10 ppm to 2% by weight, preferably of 0.05 to 0.9% by weight, very particularly preferably of 0.005 to 0.25% by weight.Topical application may be conducted with compound-containing shaped articles e.g. collars,medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils. 83 Generally it is favorable to apply solid formulations which release compounds of the invention in total amounts of 10 mg / kg to 300 mg / kg, preferably 20 mg / kg to 200 mg / kg, most preferably 25 mg / kg to 160 mg / kg body weight of the treated animal in the course of three weeks.ExamplesThe following examples illustrate the invention. A. Preparation of Compounds Materials: Unless otherwise noted, reagents and solvents were purchased at highest commercial quality and used without further purification.All reactions were monitored by thin-layer chromatography (TLC) using Merck silica gel 60 F254pre-coated plates (0.25mm). Flash chromatography was carried out with Agela technologies silica gel (Agela techno, silica irregular 40-60µm, 60A, Cat.-No. C-CS1400).1H NMR spectra were recorded on Bruker (500 MHz). Chemical shifts are expressed in ppm downfield from the internal solvent peaks for DMSO-d6(1H; δ = 2.50ppm) (1H; δ = 2.50ppm) andCD3OD (1H; δ = 3.30ppm), and J values are given in Hertz. The following abbreviations were usedto explain the multiplicities: s = singlet, d = doublet, t = triplet, q = quartet, dd = double doublet, dt = double triplet, m = multiplet, br = broad. High-resolution mass spectra were measured on a JEOL JMS-T100LP. Characterization: The compounds were characterized by coupled High Performance LiquidChromatography with mass spectrometry (HPLC / MS).Method A: Waters (ACQUITY-H Class UPLC. Analytical UHPLC column), Mass detector Qda: Agilent eclipse plus-C18 RRHD, 50 mm, 2.1 mm, 1.8 micron; mobile phase: A: 0.1% Formic acid in Water. B: 0.1% Formic acid in ACN C: 20 mM Ammonium Formate in water. Flow Rate: 0.5 mL / min, Injection Vol: 0.5 µL. Gradient: Initial 80%A,15%B and 5% C hold for 0.5 min,1.50minutes 0 % A, 95 % B and 5% C hold for 1 min, 2.51 min 80% A,15 % B and 5% C Run time: 3min column temperature 40°C. MS-method: ESI positive and negative mode; mass range (m / z) 80-1000. Method B: Waters (ACQUITY-H Class UPLC. Analytical UHPLC column), QDa Detector, Basfgeneric_PDA_3.5 mins Column: Agilent Eclipse plus C18 RRHD, 1.7um, 2.1* 50mm ; Mobilephase: A: 0.1% formic acid, B: 0.1% formic acid in Acetonitrile C: 20 mM Ammonium Formate inwater. Flow Rate: 0.5 mL / min, Injection Vol: 0.3 µL; Gradient: 15 % B + 5 % C Hold for 0.5 Mins, 1.5 min 95 %B+5%C, Hold for 1 Min, 2.6 to 3.5 min- 15 % B + 5 % C Hold for 0.9 Min, Run time: 3.5 min at 40°C. MS-method: ESI positive & Negative; mass range (m / z) 50-1200. Abbreviations used: min is minutes; ACN is acetonitrile; DCM is dichlormethane; DMF isdimethylformamide; THF is tetrahydrofuran; mL is milliliters; min is minutes; h is hour(s)Synthesis example A: Manufacture of 1-[4-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfinyl)- 1,3-benzoxazol-2-yl]-3-pyridyl]phenyl]cyclopropanecarbonitrile (compound I.1) 84 Step-1: Manufacture of 2-nitro-4-(trifluoromethylsulfinyl)phenol To a stirred solution of 2-nitro-4-(trifluoromethylsulfanyl)phenol (5g, 20.91mmol) in Trifluoroacetic acid (50mL) at 0°C was added carefully H2O2(30% in H2O solution) (4.75mL, 41.81mmol)dropwise over 10 minutes keeping temperature below 5°C. After the addition was completedreaction mixture was stirred at 0oC for 6h. The progress of the reaction mixture was monitored by TLC. After the reaction was completed reaction mixture was poured into ice cold water (500mL) and was basified with Solid NaHCO3. To the same was added sat. Sodium thiosulphate solution (50mL) and then compound was extracted with EtOAc (250mL x 4 times). The combined organiclayer was dried over Na2SO4 and concentrated in vacuum to afford 2-nitro-4-(trifluoromethylsulfinyl)phenol as yellow solid (5.2g, 97% yield). H1 NMR 1H NMR (300 MHz, DMSO-d6) δ 12.34 (bs, 1H), 8.40 (d, J = 2.0 Hz, 1H), 8.09 – 7.97 (m, 1H), 7.42 (d, J = 8.8 Hz, 1H). LC-MS: mass calculated for C7H4F3NO4S [M]+ 254.9, found 253.9 (M-1). Step-2: Manufacture of 2-amino-4-(trifluoromethylsulfinyl)phenolTo a stirred solution of 2-nitro-4-(trifluoromethylsulfinyl)phenol (4g, 15.68mmol) in a mixture ofethyl acetate (40 mL) and Ethanol (40mL) was added Stannous chloride anhydrous (11.89g, 62.7mmol) at RT and heated at 80°C for 2 hours. The TLC monitoring showed that the starting material was consumed. The reaction mixture was diluted with ethyl acetate (200mL) and water (500mL), it was basified with solid sodium bicarbonate then filtered through celite, the celite bedwas washed with ethyl acetate (500mL) and the combined organic layer was washed with brinesolution then dried over sodium sulfate and concentrated under reduced pressure to get 2-amino- 4-(trifluoromethylsulfinyl)phenol as light brown solid (3.3g, 93.5% yield). 1H NMR (300 MHz, DMSO-d6) δ 10.28 (bs, 1H), 7.06 (s, 1H), 6.96 – 6.83 (m, 2H), 5.17 (bs, 2H). LC-MS: mass calculated for C7H6F3NO2S [M]+ 225.19, found 226.2 (M+1).Step-3: Manufacture of 5-bromo-3-ethylsulfanyl-pyridine-2-carbonitrileThe mixture of 5-bromo-2-methyl-3-nitro-pyridine (10g, 44mmol) in THF (90mL) was cooled at 10°C. To this solution, solution of sodium ethane thionate (5.16g, 64.4mmol) in water (10mL) was added drop wise over 10 minutes and stirred for 1hr at 10°C. Reaction was monitored by TLC. After completion of reaction, reaction mass quench with water (100mL) and stirred for 10 min.Compound was extracted with MTBE (100mL). The organic layer was dried over Na2SO4 andconcentrated in vacuum to afford crude compound. Crude compound was stirred in 2-propanol (10mL) at 0°C for 20 minutes. Compound was filtered through Buchner funnel and washed with 85 heptane(30mL). Compound was dried under vacuum the to afford 5-bromo-3-ethylsulfanyl- pyridine-2-carbonitrile (9.3g, 87% yield).1H NMR (300 MHz, Chloroform-d) δ 8.52 (dd, J = 2.0, 0.8 Hz, 1H), 7.85 (dd, J = 2.1, 0.7 Hz, 1H), 3.09 (qd, J = 7.3, 0.8 Hz, 2H), 1.43 (td, J = 7.4, 0.8 Hz, 3H). LC-MS: mass calculated for C8H7BrN2S [M]+ 241.9, found 242.9 (M+1).Step-4: Manufacture of 5-bromo-3-ethylsulfonyl-pyridine-2-carbonitrileTo a stirred solution of 5-bromo-3-ethylsulfanyl-pyridine-2-carbonitrile (10g, 41.8mmol) in DCM (200mL) at 0°C was added mCPBA(22.6, 92mmol) over 25 minutes keeping temperature below 5°C. After the addition was completed reaction mixture was stirred at RT for 16h. The progress of the reaction mixture was monitored by TLC. After the reaction was completed reaction mixturewas poured into Sat. NaHCO3 solution (250mL) then compound was extracted with DCM (150mLx 2 times). This organic layer was again washed with Sat. NaHCO3solution(250mL). The organic layer was washed with 10% Sodium bisulfite solution(100mL). The combined organic layer was dried over Na2SO4 and concentrated in vacuum to afford Crude compound. This crude compound was stirred in 10% EtOAc-Heptane mixture (50mL) & resulting solid was filteredthrough Buchner funnel to afford pure compound (11g, 96% yield).1H NMR (300 MHz, DMSO-d6) δ 9.26 (d, J = 2.1 Hz, 1H), 8.71 (d, J = 2.1 Hz, 1H), 3.60 (q, J = 7.3 Hz, 2H), 1.23 (t, J = 7.3 Hz, 3H). GC-MS: mass calculated for C8H7BrN2O2S [M]+ 273.9, found 274.9 (M+1). Step-5: Manufacture of 5-bromo-3-ethylsulfonyl-pyridine-2-carboxylic acid H2SO4 (18mL) was added dropwise to water (9mL) at 10°C over 20 minutes keeping temperaturebelow 30°C. To this acid solution, 5-bromo-3-ethylsulfonyl-pyridine-2-carbonitrile was added (9g32mmol). This mixture was stirred 16hr maintaining reaction temperature 92°C. The progress of the reaction mixture was monitored by TLC & LCMS. After completion of reaction, RM was cooled to RT & then poured dropwise into ice-cold water(300mL) under stirring, solid precipitated out. This solid was filtered through Buchner funnel & washed thoroughly with water. The solid driedunder vacuum to get pure compound (7g,73% yield).1H NMR (300 MHz, DMSO-d6) δ 9.08 (d, J= 2.1 Hz, 1H), 8.53 (d, J = 2.1 Hz, 1H), 3.58 (q, J = 7.4 Hz, 2H), 1.20 (t, J = 7.4 Hz, 3H). LC-MS: mass calculated for C8H8BrNO4S [M]+ 292.9, found 291.9 (M-1). Step-6: Manufacture of 5-bromo-3-ethylsulfonyl-pyridine-2-carbonyl chloride To the solution of 5-bromo-3-ethylsulfonyl-pyridine-2-carboxylic acid (8g, 27.2mmol) in Toluene(160 mL) was added N,N-Dimethyl formamide (6mL, 81.6 mmol) followed by dropwise addition ofThionyl chloride (10.37mL, 136mmol) at RT over 5 mins). Reaction mixture was heated at 100°C for 2 hours. The reaction was monitored by TLC. After the completion of reaction, reaction mixture was concentrated under reduced pressure to get 5-bromo-3-ethylsulfonyl-pyridine-2-carbonyl chloride (8.5g, 97% yield). The crude product was carried further for next step without any furthercharacterization.Step-7: Manufacture of 5-bromo-3-ethylsulfonyl-N-[2-hydroxy-5- (trifluoromethylsulfinyl)phenyl]pyridine-2-carboxamide 86 To a stirred solution of 2-amino-4-(trifluoromethylsulfinyl)phenol (5g, 22.2mmol) in dry THF (100mL) at 0°C was added a solution of 5-bromo-3-ethylsulfonyl-pyridine-2-carbonyl chloride (8.3g, 26.64 mmol) in 100mL of dry THF over 10 mins. After the addition was completed reaction mixture was allowed to stir at RT for 2 hours. The progress of the reaction was monitored by TLC.After the completion of reaction, it was quenched in 300mL of ice-cold water which was thenbasified with solid NaHCO3and compound was extracted with EtOAc (250mL x 2 times). The combined organic layer was washed with brine solution then dried over sodium sulphate and concentrated under reduced pressure to get the crude product which was purified by column chromatography using 60% EtOAc in n-Heptane as an eluent to afford 5-bromo-3-ethylsulfonyl-N-[2-hydroxy-5-(trifluoromethylsulfinyl)phenyl]pyridine-2-carboxamide as yellow solid (10.6g,95.2% yield).1H NMR (300 MHz, DMSO-d6) δ 11.48 (bs, 1H), 10.27 (s, 1H), 9.14 (d, J = 2.1 Hz, 1H), 8.66 (d, J = 1.9 Hz, 1H), 8.56 (d, J = 2.1 Hz, 1H), 7.55 (dd, J = 8.5, 2.0 Hz, 1H), 7.20 (d, J = 8.5 Hz, 1H), 3.71 (q, J = 7.4 Hz, 2H), 1.22 (t, J = 7.4 Hz, 3H). LC-MS: mass calculated for C15H12BrF3N2O5S2[M]+ 501.29, found 501.0 (M+).Step-8: Manufacture of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-5-(trifluoromethylsulfinyl)-1,3-benzoxazole To a stirred solution of 5-bromo-3-ethylsulfonyl-N-[2-hydroxy-5-(trifluoromethylsulfinyl)- phenyl]pyridine-2-carboxamide (3g, 5.98mmol) in Xylene (30 mL) was added p-Toluene sulphonic acid monohydrate (2.846g, 14.961mmol).Reaction mixture was heated at 155°C using Dean-Stark for 7 hours. The progress of the reaction was monitored by TLC. After the reaction wascompleted, it was added into 150mL of ice-cold water and 150mL of EtOAc, it was then basified using solid NaHCO3and the layer was separated, compound was extracted with EtOAc (100mL). The combined organic layer was washed with brine solution then dried over sodium sulfate, concentrated under reduced pressure to get the crude product which was purified by columnchromatography using 60% EtOAc in n-Heptane as an eluent to afford 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-5-(trifluoromethylsulfinyl)-1,3-benzoxazole as beige solid (2.57g, 88.8% yield).1H NMR (300 MHz, DMSO-d6) δ 9.32 (d, J = 2.1 Hz, 1H), 8.76 (d, J = 2.1 Hz, 1H), 8.57 – 8.51 (m, 1H), 8.34 – 8.26 (m, 1H), 8.14 – 8.06 (m, 1H), 3.96 (q, J = 7.4 Hz, 2H), 1.30 (t, J = 7.4 Hz, 3H). LC-MS: mass calculated for C15H10BrF3N2O4S2[M]+ 483.27, found 485.0 (M+2).Step-9: Manufacture of 1-[4-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfinyl)-1,3-benzoxazol-2-yl]-3-pyridyl]phenyl]cyclopropanecarbonitrile To a stirred solution of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-5-(trifluoromethylsulfinyl)-1,3- benzoxazole (0.3g, 0.62mmol) in a mixture of 1,4-Dioxane(4mL) and H2O (0.4 mL) was added Potassium carbonate (0.214g, 1.55mmol) and 1-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole (0.218g, 0.93mmol). Reaction mixture was degassed with N2 gas for10mins followed by addition of [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.032g, 0.04mmol) and degassing was continued for another 5mins. After the degassing was completed reaction mixture was heated at 120°C for 2h. The progress of the reaction was 87 monitored by TLC. After the reaction was completed, it was added with 30mL of water and compound was extracted with 100mL of EtOAc (50mL x 2 times), the combined organic layer was dried over sodium sulfate, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 60% EtOAc in n-Heptane as an eluent to afforddesired product as white solid (0.19g, 58% yield). 1H NMR (300 MHz, DMSO-d6) δ 9.38 (d, J =2.0 Hz, 1H), 8.76 (s, 1H), 8.65 (d, J = 2.0 Hz, 1H), 8.51 (s, 1H), 8.32 – 8.24 (m, 2H), 8.08 (d, J = 8.4 Hz, 1H), 3.91 (q, J = 7.3 Hz, 2H), 3.82 (td, J = 7.2, 3.5 Hz, 1H), 1.30 (t, J = 7.4 Hz, 3H), 1.18 – 1.09 (m, 2H), 1.09 – 0.99 (m, 2H). LC-MS: mass calculated for C21H17F3N4O4S2[M]+ 510.51, found 511.3 (M+1). Synthesis example B: Manufacture of 2-[4-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfonyl)- 1,3-benzoxazol-2-yl]-3-pyridyl]phenyl]-2-methyl-propanenitrile (compound I.17) Step-1: Manufacture of 2-nitro-4-(trifluoromethylsulfonyl)phenolTo a stirred solution of 2-nitro-4-(trifluoromethylsulfanyl)phenol (5g, 20.91mmol) in Trifluoroaceticacid (50 mL) at 0°C was added carefully H2O2(30% in H2O) (11.85mL, 104.45mmol) dropwise over 10 mins keeping temperature below 5°C. After the addition was completed reaction mixture was stirred at 25°C for 6h. The progress of the reaction mixture was monitored by TLC. After the reaction was completed reaction mixture was poured into ice cold water (500mL) and was basifiedwith Solid NaHCO3. To the same was added sat. Sodium thiosulphate solution (100mL) and thencompound was extracted with EtOAc (250mL x 3 times). The combined organic layer was dried over Na2SO4and concentrated in vacuum to afford 2-nitro-4-(trifluoromethylsulfonyl)phenol product as yellow solid (5.7g, 95.5% yield).1H NMR (300 MHz, DMSO-d6) δ 8.19 (d, J = 2.8 Hz, 1H), 7.35 (dd, J = 9.5, 2.9 Hz, 1H), 6.50 (d, J = 9.5 Hz, 1H).LC-MS: mass calculated forC7H4F3NO5S [M]+ 270.9, found 269.9 (M-1).Step-2: Manufacture of 2-amino-4-(trifluoromethylsulfonyl)phenol To a stirred solution of 2-nitro-4-(trifluoromethylsulfonyl)phenol (3g, 11.06mmol) in a mixture of ethyl acetate (30 mL) and Ethanol (30mL) was added Stannous chloride anhydrous (8.39g, 44.25mmol) at RT and heated at 80°C for 2 hours. The TLC monitoring showed that the startingmaterial was consumed. The reaction mixture was diluted with Ethyl acetate (200mL) and water(200mL), it was basified with solid sodium bicarbonate then filtered through celite, the celite bed was washed with EtOAc (500mL) and the combined organic layer was washed with brine solution then dried over sodium sulfate and concentrated under reduced pressure to get 2-amino-4- 88 (trifluoromethylsulfonyl)phenol as light brown solid (2.6 g, 97.44% yield).1H NMR (300 MHz, DMSO-d6) δ 10.97 (s, 1H), 7.21 (d, J = 2.5 Hz, 1H), 7.16 (dd, J = 8.3, 2.5 Hz, 1H), 6.96 (d, J = 8.3 Hz, 1H), 5.37 (s, 2H). LC-MS: mass calculated for C7H6F3NO3S [M]+ 241.0, found 242.1 (M+1). Step-3: Manufacture of 5-bromo-3-ethylsulfonyl-pyridine-2-carbonyl chlorideTo the solution of 5-bromo-3-ethylsulfonyl-pyridine-2-carboxylic acid (8g, 27.2mmol) in Toluene(160mL) was added N,N-Dimethyl formamide (6mL, 81.6 mmol) followed by dropwise addition of Thionyl chloride (10.37mL, 136mmol) at RT over 5 mins). Reaction mixture was heated at 100°C for 2 hours. The reaction was monitored by TLC. After the completion of reaction, reaction mixture was concentrated under reduced pressure to get 5-bromo-3-ethylsulfonyl-pyridine-2-carbonylchloride (8.5g, 97% yield). The crude product was carried further for next step without any furthercharacterization. Step-4: Manufacture of 5-bromo-3-ethylsulfonyl-N-[2-hydroxy-5- (trifluoromethylsulfonyl)phenyl]pyridine-2-carboxamide To a stirred solution of 2-amino-4-(trifluoromethylsulfonyl)phenol (2.46g, 10.2mmol) in dry THF(20 mL) at 0°C was added a solution of 5-bromo-3-ethylsulfonyl-pyridine-2-carbonyl chloride(3.18g, 10.2 mmol) in 10mL of dry THF over 10 mins. After the addition was completed reaction mixture was allowed to stir at RT for 2 hours. The progress of the reaction was monitored by TLC. After the completion of reaction, it was quenched in 100mL of ice-cold water which was then basified with solid NaHCO3and compound was extracted with EtOAc (150mL x 2 times). Thecombined organic layer was washed with brine solution then dried over sodium sulphate andconcentrated under reduced pressure to get the crude product which was purified by column chromatography using 60% EtOAc in n-Heptane as an eluent to afford 5-bromo-3-ethylsulfonyl- N-[2-hydroxy-5-(trifluoromethylsulfonyl)phenyl]pyridine-2-carboxamide as yellow solid (5g, 90.02% yield).1H NMR (300 MHz, DMSO-d6) δ 10.40 (s, 1H), 9.14 (d, J = 2.1 Hz, 1H), 8.79 (d, J= 2.5 Hz, 1H), 8.57 (d, J = 2.1 Hz, 1H), 7.71 (dd, J = 8.8, 2.5 Hz, 1H), 7.13 (d, J = 8.8 Hz, 1H),3.73 (q, J = 7.4 Hz, 2H), 1.22 (t, J = 7.4 Hz, 3H).LC-MS: mass calculated for C15H12BrF3N2O6S2[M]+ 515.92, found 519.1 (M+2). Step-5: Manufacture of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-5-(trifluoromethylsulfonyl)- 1,3-benzoxazoleTo a stirred solution of 5-bromo-3-ethylsulfonyl-N-[2-hydroxy-5-(trifluoromethylsulfonyl)-phenyl]pyridine-2-carboxamide (2.5g, 4.83 mmol) in Xylene (25 mL) was added p-Toluene sulphonic acid monohydrate (2.75g, 14.5 mmol). Reaction mixture was heated at 155oC using Dean-Stark for 7 hours. The progress of the reaction was monitored by TLC. After the reaction was completed, it was added into 150mL of ice-cold water and 150mL of EtOAc, it was thenbasified using solid NaHCO3 and the layer was separated, compound was extracted with EtOAc(100mL). The combined organic layer was washed with brine solution then dried over sodium sulfate, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 60% EtOAc in n-Heptane as an eluent to afford 2-(5-bromo-3- 89 ethylsulfonyl-2-pyridyl)-5-(trifluoromethylsulfonyl)-1,3-benzoxazole as beige solid (1.85 g, 76.67% yield).1H NMR (300 MHz, DMSO-d6) δ 9.34 (d, J = 2.1 Hz, 1H), 8.86 (d, J = 1.9 Hz, 1H), 8.78 (d, J = 2.1 Hz, 1H), 8.41 (dd, J = 8.8, 0.7 Hz, 1H), 8.34 (dd, J = 8.7, 1.9 Hz, 1H), 3.96 (q, J = 7.4 Hz, 2H), 1.30 (t, J = 7.4 Hz, 3H).LC-MS: mass calculated for C15H10BrF3N2O5S2[M]+ 497.91, found499.0 (M+2).Step-6: Manufacture of 2-[4-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfonyl)-1,3-benzoxazol- 2-yl]-3-pyridyl]phenyl]-2-methyl-propanenitrile To a stirred solution of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-5-(trifluoromethylsulfonyl)-1,3- benzoxazole(0.2g, 0.4mmol) in a mixture of 1,4-Dioxane (4mL) and H2O (0.5 mL) was addedPotassium carbonate (0.111g, 0.8mmol) and [4-(1-cyano-1-methyl-ethyl)phenyl]boronic acid(0.091g, 0.48mmol). Reaction mixture was degassed with N2gas for 10mins followed by addition of [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.029g, 0.04mmol) and degassing was continued for another 5mins. After the degassing was completed reaction mixture was heated at 110oC for 4h. The progress of the reaction was monitored by TLC. After the reactionwas completed, it was added with 30mL of water and compound was extracted with 80mL ofEtOAc (40mL x 2 times), the combined organic layer was dried over sodium sulfate, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 60% EtOAc in n-Heptane as an eluent to afford desired product as white solid (0.14g, 60.27% yield).1H NMR (300 MHz, DMSO-d6) δ 9.50 (d, J = 2.1 Hz, 1H), 8.85 (d, J = 1.9 Hz, 1H),8.77 (d, J = 2.1 Hz, 1H), 8.42 (d, J = 8.7 Hz, 1H), 8.34 (dd, J = 8.7, 1.9 Hz, 1H), 8.10 – 8.00 (m,2H), 7.83 – 7.72 (m, 2H), 3.97 (q, J = 7.4 Hz, 2H), 1.77 (s, 6H), 1.33 (t, J = 7.4 Hz, 3H). LC-MS: mass calculated for C25H20F3N3O5S2[M]+ 563.07, found 564.3 (M+1). Synthesis example C: Manufacture of 2-[4-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfonyl)-1,3-benzoxazol-2-yl]-3-pyridyl]phenyl]-2-methyl-propanenitrile (compound I.12) Step-1: Manufacture of 2-(3-ethylsulfonyl-5-vinyl-2-pyridyl)-5-(trifluoromethylsulfinyl)-1,3- benzoxazole To a stirred solution of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-5-(trifluoromethylsulfinyl)-1,3-benzoxazole (0.5g, 1.03mmol) in 1,4-Dioxane (5mL) was added Pd(dppf)Cl2 (0.076g, 0.1mmol)and reaction mixture was degassed with N2gas for 10 mins followed by addition of vinyl tributyltin (0.492g, 1.55mmol) and degassing was continued for another 5 mins. After the degassing was completed reaction mixture was heated at 110°C for 5h. The progress of the reaction was 90 monitored by TLC. After the reaction was completed, it was added with 30mL of water and compound was extracted with 50mL of EtOAc (25mL x 2 times), the combined organic layer was dried over sodium sulfate, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 15% EtOAc in n-Heptane as an eluent to afford 2-(3-ethylsulfonyl-5-vinyl-2-pyridyl)-5-(trifluoromethylsulfinyl)-1,3-benzoxazole as white solid(0.35g, 78.59% yield).1H NMR (300 MHz, DMSO-d6) δ 9.26 (d, J = 2.0 Hz, 1H), 8.61 (d, J = 2.0 Hz, 1H), 8.52 (d, J = 1.7 Hz, 1H), 8.28 (dd, J = 8.7, 0.6 Hz, 1H), 8.09 (ddd, J = 8.7, 1.8, 0.8 Hz, 1H), 7.05 (dd, J = 17.7, 11.1 Hz, 1H), 6.38 (d, J = 17.8 Hz, 1H), 5.87 – 5.67 (s, 1H), 3.92 (q, J = 7.4 Hz, 2H), 1.29 (t, J = 7.4 Hz, 3H). LC-MS: mass calculated for C17H13F3N2O4S2[M]+ 430.42,found 431.2 (M+1).Step 2: Manufacture of 5-ethylsulfonyl-6-[5-(trifluoromethylsulfinyl)-1,3-benzoxazol-2- yl]pyridine-3-carbaldehyde To a stirred solution of 2-(3-ethylsulfonyl-5-vinyl-2-pyridyl)-5-(trifluoromethylsulfinyl)-1,3- benzoxazole (0.350g, 0.81mmol) in 1,4-Dioxane (10mL) at 0°C was added osmium tetroxide(0.010g, 0.04mmol) and reaction mixture was stirred at 0°C for 10 mins. The sodium periodate(0.641g, 3mmol) was dissolved in water (2mL) and added to reaction mixture at 0°C and stirring was continued for another 3 h at 0-25oC. The progress of the reaction was monitored by TLC. After the reaction was completed, it was quenched with 50mL of saturated sodium bicarbonate solution and compound was extracted with 100mL of EtOAc (50mL x 2 times), the combinedorganic layer was dried over sodium sulfate, concentrated under reduced pressure to get thecrude product which was purified by column chromatography using 20% EtOAc in n-Heptane as an eluent to afford 5-ethylsulfonyl-6-[5-(trifluoromethylsulfinyl)-1,3-benzoxazol-2-yl]pyridine-3- carbaldehyde as white solid (0.220g, 62.57% yield).1H NMR (300 MHz, DMSO-d6) δ 10.32 (s, 1H), 9.54 (d, J = 1.8 Hz, 1H), 8.95 (d, J = 1.8 Hz, 1H), 8.57 (d, J = 1.7 Hz, 1H), 8.32 (dd, J = 8.7,0.7 Hz, 1H), 8.16 – 8.07 (m, 1H), 4.06 – 3.87 (m, 2H), 1.31 (t, J = 7.4 Hz, 3H). LC-MS: masscalculated for C16H11F3N2O5S2[M]+ 432.39, found 433.2 (M+1). Step-3: Manufacture of 2-[5-(5,5-difluoro-1,3-dioxan-2-yl)-3-ethylsulfonyl-2-pyridyl]-5- (trifluoromethylsulfinyl)-1,3-benzoxazole To the solution of 5-ethylsulfonyl-6-[5-(trifluoromethylsulfinyl)-1,3-benzoxazol-2-yl] pyridine-3-carbaldehyde (0.1g, 0.23mmol) in toluene(10mL), 2,2-difluoropropane-1,3-diol (0.051g 0.46mmol)& p-Toluene sulfonic acid (0.132g, 0.69mmol) were added. Dean stark apparatus is attached to reaction assembly. This reaction mixture was stirred at 130°C for 16h. The progress of the reaction mixture was monitored by TLC & LCMS. After completion of reaction, reaction mixture was cooled to room temperature & water (10mL) was added to reaction mixture. Compound wasextracted using EtOAc (25ml x 2times). The organic layer was washed with 10% Sodium bisulfitesolution(100mL). The combined organic layer was dried over Na2SO4and concentrated in vacuum to afford Crude compound. This crude compound was purified by column 91 chromatography using EtOAc & Heptane as eluent to afford pure 2-[5-(5,5-difluoro-1,3-dioxan-2- yl)-3-ethylsulfonyl-2-pyridyl]-5-(trifluoromethylsulfinyl)-1,3-benzoxazole (0.07g, 57% yield).1H NMR (300 MHz, DMSO-d6) δ 9.17 (d, J = 1.9 Hz, 1H), 8.58 – 8.52 (m, 2H), 8.31 (dd, J = 8.7, 0.6 Hz, 1H), 8.15 – 8.06 (m, 1H), 6.15 (s, 1H), 4.43 (dt, J = 14.9, 12.0 Hz, 3H), 4.28 (d, J = 12.0 Hz,1H), 3.98 (q, J = 7.4 Hz, 2H), 1.28 (t, J = 7.4 Hz, 3H). LC-MS: mass calculated for C19H15F5N2O6S2[M]+526, found 527 [M+1]+. Synthesis example D: Manufacture of 2-[5-(4-cyclopropylimidazol-1-yl)-3-ethylsulfonyl-2- pyridyl]-5-(trifluoromethylsulfinyl)-1,3-benzoxazole (compound I.11) Step-1: Manufacture of [5-ethylsulfonyl-6-[5-(trifluoromethylsulfinyl)-1,3-benzoxazol-2-yl]- 3-pyridyl]boronic acid. To a stirred solution of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-5-(trifluoromethylsulfinyl)-1,3- benzoxazole (2g, 4.14mmol) in 1,4 Dioxane (20 mL) at 20°C was added Bis(pinacolato)diboron(1.26 gm, 4.97mmol) and Potassium acetate (0.812gm, 8.28mmol). Degassed reaction mixturewith N2gas for 10 min. Then added [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) DCM complex (0.169gm, 0.21mmol). After the addition was completed reaction mixture was heated at 95°C for 3h. The progress of the reaction mixture was monitored by TLC. After the reaction was completed reaction mixture was poured into water (200mL) and then compound wasextracted with EtOAc (100mL x 3 times). The combined organic layer was dried over Na2SO4 andconcentrated in vacuum to crude material in it added 100 ml of MTBE and stirred for 30 min. The solution was filtered and filtrate was concentrated in vacuum to afford [5-ethylsulfonyl-6-[5- (trifluoromethylsulfinyl)-1,3-benzoxazol-2-yl]-3-pyridyl]boronic acid as beige solid (1.5g, 80% yield).1H NMR (300 MHz, DMSO) δ 9.22 (d, J = 1.5 Hz, 1H), 8.65 (d, J = 1.5 Hz, 1H), 8.55 (d, J= 1.7 Hz, 1H), 8.38 – 8.23 (m, 1H), 8.11 (dd, J = 8.6, 1.7 Hz, 1H), 3.97 (q, J = 7.4 Hz, 2H), 1.29(t, J = 7.4 Hz, 3H). LC-MS: mass calculated for C15H12BF3N2O6S2[M]+ 448.0, found 449.2 (M+1). Step-2: Manufacture of 1-[5-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfinyl)-1,3-benzoxazol- 2-yl]-3-pyridyl]-2-pyridyl]cyclopropanecarbonitrile To a stirred solution of [5-ethylsulfonyl-6-[5-(trifluoromethylsulfinyl)-1,3-benzoxazol-2-yl]-3-pyridyl]boronic acid (200mg, 0.45mmol), and 1-(5-bromo-2-pyridyl)cyclopropanecarbonitrile(100mg, 0.45mmol), in 1,4-dioxane (2mL) was added potassium carbonate (185mg, 1.34mmol) and water (0.05mL). Reaction mixture was degassed by Nitrogen for 10 min. then Pd(dppf)Cl2·DCM (36mg, 0.04mmol) was added. Reaction mixture was stirred at 95°C for 16h. 92 The progress of the reaction was monitored by TLC. The resulting mixture was cooled to room temperature. Filtered the reaction mixture through celite and bed was washed with ethyl acetate. Combined filtrate was washed with water (50ml x 2 times). The combined organic layer was dried over Na2SO4and concentrate under reduced pressure. Purify the resulting crude mixture bycolumn chromatography to afford 1-[5-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfinyl)-1,3-benzoxazol-2-yl]-3-pyridyl]-2-pyridyl]cyclopropanecarbonitrile as white solid (65 mg, 26 % yield). 1H NMR (300 MHz, CDCl3) δ 9.15 (s, 1H), 8.73 (dd, J = 21.0, 2.1 Hz, 2H), 8.31 (s, 1H), 7.99 (dd, J = 8.2, 2.3 Hz, 1H), 7.96 – 7.75 (m, 3H), 4.04 (q, J = 7.4 Hz, 2H), 1.95 – 1.73 (m, 4H), 1.42 (t, J = 7.4 Hz, 3H). LC-MS: mass calculated for C24H17F3N4O4S2[M]+ 546.06, found 547.1 (M+1). Synthesis example E: Manufacture of dicyclopropyl-[4-[5-ethylsulfonyl-6-[5- (trifluoromethylsulfinyl)-1,3-benzoxazol-2-yl]-3-pyridyl]phenyl]imino-oxo-λ⁶-sulfane (compound I.28) Step 1: Manufacture of dicyclopropyl-imino-oxo-λ⁶-sulfaneThe titled compound was prepared according as described in WO2024008128.1H NMR (300 MHz, Chloroform-d) δ 2.55 (tt, J = 8.0, 4.8 Hz, 2H), 1.20 (tt, J = 7.1, 3.0 Hz, 4H), 1.04 (tdd, J = 9.1, 6.6, 3.9 Hz, 4H). Step 2: Manufacture of (4-bromophenyl)imino-dicyclopropyl-oxo-λ⁶-sulfaneThe titled compound was prepared as described in Advanced Synthesis & Catalysis, 360(6),1088–1093.1H NMR (300 MHz, Chloroform-d) δ 7.29 (d, J = 8.7 Hz, 3H), 6.99 – 6.93 (m, 2H), 2.52 (tt, J = 7.9, 4.8 Hz, 2H), 1.40 – 1.28 (m, 2H), 1.25 – 1.15 (m, 2H), 1.12 – 0.96 (m, 4H). LC- MS: mass calculated for C12H14BrNOS [M]+ 299, found 300 (M+1). Step 3: Manufacture of dicyclopropyl-oxo-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]imino-λ⁶-sulfaneThe titled compound was prepared as described in WO2016113299 A1.1H NMR (300 MHz, DMSO-d6) δ 7.47 – 7.43 (m, 2H), 6.94 – 6.89 (m, 2H), 2.76 (tt, J = 7.6, 5.1 Hz, 2H), 1.14 – 1.09 (m, 2H), 1.07 (s, 12H), 1.06 – 0.97 (m, 6H). LC-MS: mass calculated for C18H26BNO3S [M]+ 347, found 348 (M+1).Step 4: Manufacture of dicyclopropyl-[4-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfinyl)-1,3-benzoxazol-2-yl]-3-pyridyl]phenyl]imino-oxo-λ⁶-sulfane To a stirred solution of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-5-(trifluoromethylsulfinyl)-1,3- benzoxazole (0.1 g, 0.207mmol) in a mixture of 1,4-Dioxane (2mL) and H2O (0.25mL) was added 93 Potassium carbonate (0.055g, 0.414mmol) and dicyclopropyl-oxo-[4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)phenyl]imino-λ⁶-sulfane (0.071g, 0.207mmol). Reaction mixture was degassed with nitrogen gas for 10mins followed by addition of [1,1′-Bis(diphenylphosphino)- ferrocene]dichloropalladium(II) (0.01 g, 0.02mmol) and degassing was continued for another 5mins. After the degassing was completed reaction mixture was heated at 110°C for 4h. Theprogress of the reaction was monitored by TLC. After the reaction was completed, it was quenched with 30mL of water and compound was extracted with 80mL of EtOAc (40mL x 2 times), the combined organic layer was dried over sodium sulfate, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 60% EtOAc in n-Heptane as an eluent to afford dicyclopropyl-[4-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfinyl)-1,3-benzoxazol-2-yl]-3-pyridyl]phenyl]imino-oxo-λ⁶-sulfane as yellow solid (0.05g, 37% yield1H NMR (300 MHz, DMSO-d6) δ 9.41 (d, J = 2.1 Hz, 1H), 8.64 (d, J = 2.2 Hz, 1H), 8.52 (d, J = 1.4 Hz, 1H), 8.29 (d, J = 8.6 Hz, 1H), 8.09 (d, J = 8.9 Hz, 1H), 7.81 (d, J = 8.6 Hz, 2H), 7.13 (d, J = 8.6 Hz, 2H), 3.96 (q, J = 7.3 Hz, 2H), 2.85 (tt, J = 7.7, 5.0 Hz, 2H), 1.31 (t, J = 7.4 Hz, 3H), 1.27 – 1.14(m, 4H), 1.14 – 1.02 (m, 4H).19F NMR (282 MHz, DMSO-d6) δ -73.71, -74.15 (d, J = 5.6 Hz), -74.17. LC-MS: mass calculated for C27H24F3N3O5S3[M]+623 , found 624 [M+1]+Synthesis example F: Manufacture of [4-[5-ethylsulfonyl-6-[5-[N-methyl-S- (trifluoromethyl)sulfonimidoyl]-1,3-benzoxazol-2-yl]-3-pyridyl]phenyl] methanesulfonate(compound I.32) Step 1: Manufacture of 5-bromo-3-ethylsulfonyl-N-[2-hydroxy-5- (trifluoromethylsulfanyl)phenyl]pyridine-2-carboxamide. To a stirred solution of 2-amino-4-(trifluoromethylsulfanyl)phenol (2.40g, 11.93mmol) in dry THF(20mL) at 0°C was added a solution of 5-bromo-3-ethylsulfonyl-pyridine-2-carbonyl chloride(3.7g,11.93mmol) in 10mL of dry THF over 10 mins. After the addition was completed reaction mixture was allowed to stir at room temperature for 2 hours. The progress of the reaction was monitored by TLC. After the completion of reaction, it was quenched in 100mL of ice-cold water which was then basified with solid NaHCO3and compound was extracted with EtOAc (150mL x2 times). The combined organic layer was washed with brine solution then dried over sodiumsulfate and concentrated under reduced pressure to get the crude product which was purified by column chromatography using 50% EtOAc in n-Heptane as an eluent to afford 5-bromo-3- ethylsulfonyl-N-[2-hydroxy-5-(trifluoromethylsulfanyl)phenyl]pyridine-2-carboxamide as yellow 94 solid (5.05 g, 91.05% yield).1H NMR (300 MHz, DMSO-d6) δ 11.04 (s, 1H), 10.13 (s, 1H), 9.13 (d, J = 2.1 Hz, 1H), 8.55 (d, J = 2.1 Hz, 1H), 8.46 (d, J = 2.3 Hz, 1H), 7.38 (dd, J = 8.4, 2.3 Hz, 1H), 7.06 (d, J = 8.4 Hz, 1H), 3.72 (q, J = 7.4 Hz, 2H), 1.22 (t, J = 7.4 Hz, 3H). LC-MS: mass calculated for C15H12BrF3N2O4S2[M]+ 483.93, found 487 (M+2).Step 2: Manufacture of [4-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfanyl)-1,3-benzoxazol-2-yl]-3-pyridyl]phenyl] methanesulfonate. The titled compound was prepared by Suzuki coupling reaction as described for the example E.1H NMR (300 MHz, DMSO- d6) δ 9.48 (d, J = 2.1 Hz, 1H), 8.74 (d, J = 2.1 Hz, 1H), 8.40 (d, J = 1.8 Hz, 1H), 8.16 – 8.06 (m, 3H), 7.91-7.94 (dd, J = 8.5, 1.8 Hz, 1H), 7.66 – 7.56 (m, 2H), 3.96(q, J = 7.4 Hz, 2H), 3.48 (s, 3H), 1.32 (t, J = 7.4 Hz, 3H). LC-MS: mass calculated forC22H17F3N2O6S3[M]+ 558, found 559 (M+1). Step-3: Manufacture of [4-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfonimidoyl)-1,3- benzoxazol-2-yl]-3-pyridyl]phenyl] methane sulfonate. To a stirred solution of [4-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfanyl)-1,3-benzoxazol-2-yl]-3-pyridyl]phenyl] methane sulfonate (0.100g, 0.18mmol) in 2,2,3,3,4,4,5,5-Octafluoro-1-pentanol(3mL) at room temperature, was added Ammonium carbamate (0.042g, 0.54mmol) followed by (Diacetoxyiodo)benzene (0.231g, 0.72mmol) . The resultant reaction mixture was stirred at the room temperature for 16 hours. Reaction was monitored by TLC, after the completion of reaction, above reaction mixture was quenched by saturated NH4Cl solution (30mL) and was extractedwith ethyl acetate (30mL x 2), organic layer was washed with (20mL) of brine. The combinedorganic layer was dried over Na2SO4and concentrated under reduced pressure to get crude mass. Crude was purified by column chromatography eluting 20%-30% with ethyl acetate in heptane gradient to afford [4-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfonimidoyl)-1,3-benzoxazol- 2-yl]-3-pyridyl] phenyl] methane sulfonate as a white solid (0.040g, 36% yield).1H NMR (300 MHz,DMSO- d6): δ 9.50 (d, J = 2.1 Hz, 1H), 8.76 (d, J = 2.1 Hz, 1H), 8.66 (s, 1H), 8.37 – 8.26 (m, 2H),8.17 – 8.07 (m, 2H), 7.65 – 7.56 (m, 2H), 7.13 (s, 1H), 3.97 (q, J = 7.3 Hz, 2H), 3.48 (s, 3H),1.32 (t, J = 7.4 Hz, 3H). LC-MS: mass calculated for C22H18F3N3O7S3[M]+589, found 590 [M+1]+. Step-4: Manufacture of [4-[5-ethylsulfonyl-6-[5-[N-methyl-S-(trifluoromethyl)- sulfonimidoyl]-1,3-benzoxazol-2-yl]-3-pyridyl]phenyl] methanesulfonate.To a stirred solution of [4-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfonimidoyl)-1,3-benzoxazol-2-yl]-3-pyridyl]phenyl] methane sulfonate (0.025g, 0.04mmol) in acetonitrile (5mL) at 27°C, was added potassium carbonate (0.06g, 0.139mmol) followed by methyl iodide (10mg, 0.06mol) . The resultant reaction mixture was stirred at 60°C for 1 hour. Reaction was monitored by TLC, after the completion of reaction, above reaction mixture was quenched by saturated NH4Cl solution(20mL) and was extracted with ethyl acetate (20mL x 2), organic layer was washed with (20mL)of brine. The combined organic layers were dried over NaSO4and concentrated under reduced pressure to get crude mass. Crude was purified by column chromatography eluting 15%-25% 95 with ethyl acetate in heptane gradient to afford [4-[5-ethylsulfonyl-6-[5-[N-methyl-S- (trifluoromethyl)sulfonimidoyl]-1,3-benzoxazol-2-yl]-3-pyridyl]phenyl] methanesulfonate as a white solid (0.022g, 80% yield).1H NMR (300 MHz, DMSO- d6): δ 9.49 (d, J = 2.1 Hz, 1H), 8.76 (d, J = 2.1 Hz, 1H), 8.67 (s, 1H), 8.35 – 8.25 (m, 2H), 8.11 (d, J = 8.7 Hz, 2H), 7.60 (d, J = 8.7 Hz,2H), 3.97 (q, J = 7.4 Hz, 2H), 3.48 (s, 3H), 3.07 (d, J = 2.3 Hz, 3H), 1.32 (t, J = 7.4 Hz, 3H).19FNMR (282 MHz, DMSO) δ -71.91 (F). LC-MS: mass calculated for C23H20F3N3O7S3[M+H]+603, found 604 [M+1]+. Synthesis example G: Manufacture of 2-[4-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfonyl)-1,3-benzoxazol-2-yl]-3-pyridyl]pyrazol-1-yl]-2-methyl-propanenitrile (compound I.23) Step-1: Manufacture of 2-nitro-4-(trifluoromethylsulfonyl)phenol To a stirred solution of 2-nitro-4-(trifluoromethylsulfanyl)phenol (5g, 20.91mmol) in trifluoroacetic acid (50 mL) at 0°C was added carefully H2O2(30% in H2O) (11.85mL, 104.45mmol) dropwiseover 10mins keeping temperature below 5°C. After the addition was completed reaction mixturewas stirred at 25°C for 6h. The progress of the reaction mixture was monitored by TLC. After the reaction was completed reaction mixture was poured into ice cold water (500mL) and was basified with solid NaHCO3. To the same was added sat. sodium thiosulphate solution (100mL) and then compound was extracted with EtOAc (250mL x 3 times). The combined organic layer was driedover Na2SO4 and concentrated in vacuum to afford 2-nitro-4-(trifluoromethylsulfonyl)phenolproduct as yellow solid (5.7g, 95.5% yield).1H NMR (300 MHz, DMSO-d6) δ 8.19 (d, J = 2.8 Hz, 1H), 7.35 (dd, J = 9.5, 2.9 Hz, 1H), 6.50 (d, J = 9.5 Hz, 1H).LC-MS: mass calculated for C7H4F3NO5S [M]+ 270.9, found 269.9 (M-1). Step-2: Manufacture of 2-amino-4-(trifluoromethylsulfonyl)phenolTo a stirred solution of 2-nitro-4-(trifluoromethylsulfonyl)phenol (3g, 11.06mmol) in a mixture ofethyl acetate (30 mL) and Ethanol (30mL) was added anhydrous stannous chloride (8.39g, 44.25mmol) at room temperature and heated at 80°C for 2 hours. The TLC monitoring showed that the starting material was consumed. The reaction mixture was diluted with Ethyl acetate (200mL) and water (200mL), it was basified with solid sodium bicarbonate then filtered throughcelite, the celite bed was washed with EtOAc (500mL) and the combined organic layer waswashed with brine solution then dried over sodium sulfate and concentrated under reduced pressure to get 2-amino-4-(trifluoromethylsulfonyl)phenol as light brown solid (2.6g, 97.44% 96 yield).1H NMR (300 MHz, DMSO-d6) δ 10.97 (s, 1H), 7.21 (d, J = 2.5 Hz, 1H), 7.16 (dd, J = 8.3, 2.5 Hz, 1H), 6.96 (d, J = 8.3 Hz, 1H), 5.37 (s, 2H). LC-MS: mass calculated for C7H6F3NO3S [M]+ 241.0, found 242.1 (M+1). Step-3: Manufacture of 5-bromo-3-ethylsulfonyl-pyridine-2-carbonyl chlorideTo the solution of 5-bromo-3-ethylsulfonyl-pyridine-2-carboxylic acid (8g, 27.2mmol) in Toluene(160mL) was added N,N-Dimethyl formamide (6mL, 81.6 mmol) followed by dropwise addition of Thionyl chloride (10.37mL, 136mmol) at ROOM TEMPERATURE over 5mins). Reaction mixture was heated at 100°C for 2 hours. The reaction was monitored by TLC. After the completion of reaction, reaction mixture was concentrated under reduced pressure to get 5-bromo-3-ethylsulfonyl-pyridine-2-carbonyl chloride (8.5g, 97% yield). The crude product was used for thenext step without any further characterization. Step-4: Manufacture of 5-bromo-3-ethylsulfonyl-N-[2-hydroxy-5-(trifluoromethylsulfonyl)- phenyl]pyridine-2-carboxamide To a stirred solution of 2-amino-4-(trifluoromethylsulfonyl)phenol (2.46g, 10.2mmol) in dry THF(20 mL) at 0oC was added a solution of 5-bromo-3-ethylsulfonyl-pyridine-2-carbonyl chloride(3.18g, 10.2mmol) in 10mL of dry THF over 10mins. After the addition was completed reaction mixture was allowed to stir at room temperature for 2 hours. The progress of the reaction was monitored by TLC. After the completion of reaction, it was quenched in 100mL of ice-cold water which was then basified with solid NaHCO3and compound was extracted with EtOAc (150mL x2 times). The combined organic layer was washed with brine solution then dried over sodiumsulphate and concentrated under reduced pressure to get the crude product which was purified by column chromatography using 60% EtOAc in n-Heptane as an eluent to afford 5-bromo-3- ethylsulfonyl-N-[2-hydroxy-5-(trifluoromethylsulfonyl)phenyl]pyridine-2-carboxamide as yellow solid (5 g, 90.02% yield).1H NMR (300 MHz, DMSO-d6) δ 10.40 (s, 1H), 9.14 (d, J = 2.1 Hz, 1H),8.79 (d, J = 2.5 Hz, 1H), 8.57 (d, J = 2.1 Hz, 1H), 7.71 (dd, J = 8.8, 2.5 Hz, 1H), 7.13 (d, J = 8.8Hz, 1H), 3.73 (q, J = 7.4 Hz, 2H), 1.22 (t, J = 7.4 Hz, 3H). LC-MS: mass calculated for C15H12BrF3N2O6S2[M]+ 515.92, found 519.1 (M+2). Step-5: Manufacture of 2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-5-(trifluoromethylsulfonyl)- 1,3-benzoxazoleTo a stirred solution of 5-bromo-3-ethylsulfonyl-N-[2-hydroxy-5-(trifluoromethylsulfonyl)-phenyl]pyridine-2-carboxamide (2.5g, 4.83mmol) in Xylene (25mL) was added p-toluene sulphonic acid monohydrate (2.75g, 14.5mmol). Reaction mixture was heated at 155°C using Dean-Stark apparatus for 7 hours. The progress of the reaction was monitored by TLC. After the reaction was completed, it was quenched with 150mL of ice-cold water and 150mL of EtOAc wasadded, it was then basified using solid NaHCO3 and the layer was separated, compound wasextracted with EtOAc (100mL). The combined organic layer was washed with brine solution then dried over sodium sulfate, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 60% EtOAc in n-Heptane as an eluent to afford 2- 97 (5-bromo-3-ethylsulfonyl-2-pyridyl)-5-(trifluoromethylsulfonyl)-1,3-benzoxazole as beige solid (1.85 g, 76.67% yield).1H NMR (300 MHz, DMSO-d6) δ 9.34 (d, J = 2.1 Hz, 1H), 8.86 (d, J = 1.9 Hz, 1H), 8.78 (d, J = 2.1 Hz, 1H), 8.41 (dd, J = 8.8, 0.7 Hz, 1H), 8.34 (dd, J = 8.7, 1.9 Hz, 1H), 3.96 (q, J = 7.4 Hz, 2H), 1.30 (t, J = 7.4 Hz, 3H).LC-MS: mass calculated for C15H10BrF3N2O5S2[M]+ 497.91, found 499.0 (M+2).Step-6: Manufacture of (4-bromophenyl)-imino-oxo-(trifluoromethyl)-λ⁶-sulfane To a stirred solution of 1-bromo-4-(trifluoromethylsulfanyl)benzene (0.2g, 0.78mmol) in 2,2,2- Trifluoroethanol (2mL) was added Diacetoxyiodo benzene(0.626g, 1.94mmol) and Ammonium carbamate (0.091g, 1.17mmol). The reaction mixture was stirred at 25°C for 24h. The progressof the reaction was monitored by TLC. After the reaction was completed, the reaction mixture wasevaporated under reduced pressure. To the residue was added with 10mL of water and compound was extracted with 30mL of EtOAc (15mL x 2 times), the combined organic layer was dried over sodium sulfate, concentrated under reduced pressure to get the crude (4- bromophenyl)-imino-oxo-(trifluoromethyl)-λ⁶-sulfane as colorless sticky solid (0.220g, 98.15%yield) which was used as such for the next step. Product was confirmed by LCMS of the crude.LC-MS: mass calculated for C7H5BrF3NOS [M]+ 288.08, found 288 (M+). Step-7: Manufacture of 4-bromophenyl)-methylimino-oxo-(trifluoromethyl)-λ⁶-sulfane To a stirred solution of crude (4-bromophenyl)-imino-oxo-(trifluoromethyl)-λ⁶-sulfane (0.220g, 0.76 mmol) in Acetonitrile (2mL) and Potassium carbonate (0.100g, 0.72 mmol) was addedIodomethane (0.103 g, 0.72 mmol) at 0oC and reaction mixture was heated to 80oC for 1.5h. Theprogress of the reaction was monitored by TLC. After the reaction was completed, it was added with 20mL of water and compound was extracted with 30mL of EtOAc (15mL x 2 times), the combined organic layer was dried over sodium sulfate, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 15% EtOAc in n-Heptane as an eluent to afford 4-bromophenyl)-methylimino-oxo-(trifluoromethyl)-λ⁶-sulfane ascolorless liquid (0.120 g, 52.01% yield).1H NMR (300 MHz, DMSO-d6) δ 7.99 (s, 4H), 2.99 (q, J = 2.3 Hz, 4H).1H NMR (500 MHz, Chloroform-d) δ 7.93 (d, J = 8.6 Hz, 2H), 7.74 (d, J = 8.7 Hz, 2H), 3.08 (q, J = 2.2 Hz, 4H). LC-MS: mass calculated for C8H7BrF3NOS [M]+ 302.11, found 304.0 (M+2).Step-8: Manufacture of methylimino-oxo-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-(trifluoromethyl)-λ⁶-sulfane To a stirred solution of (4-bromophenyl)-methylimino-oxo-(trifluoromethyl)-λ⁶-sulfane (0.120 g, 0.4mmol) in 1,4-Dioxane (4mL) was added Potassium acetate (0.078 g, 0.79 mmol) and bis(pinacolato)diborane (0.121 g, 0.48 mmol). Reaction mixture was degassed with N2 gas for 10min followed by addition of [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.017 g,0.02 mmol) and degassing was continued for another 5 mins. After the degassing was completed reaction mixture was heated at 110oC for 4h. The progress of the reaction was monitored by TLC. After the reaction was completed, it was quenched with 20mL of water and compound was 98 extracted with 30mL of EtOAc (15mL x 2 times), the combined organic layer was dried over sodium sulfate, concentrated under reduced pressure to get the crude product which was purified by column chromatography using 15% EtOAc in n-Heptane as an eluent to afford methylimino- oxo-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-(trifluoromethyl)-λ⁶-sulfane as whitesolid (0.135 g, 97.33% yield). LC-MS: mass calculated for C14H19BF3NO3S [M]+ 349.17, found350.1 (M+1). Step-9: Manufacture of [4-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfonyl)-1,3-benzoxazol-2- yl]-3-pyridyl]phenyl]-methylimino-oxo-(trifluoromethyl)-λ⁶-sulfane Synthesized as described for the synthesis of product E to afford [4-[5-ethylsulfonyl-6-[5-(trifluoromethylsulfonyl)-1,3-benzoxazol-2-yl]-3-pyridyl]phenyl]-methylimino-oxo-(trifluoromethyl)-λ⁶-sulfane as white solid (0.120g, 62.11% yield).1H NMR (300 MHz, DMSO-d6) δ 9.57 (d, J = 2.1 Hz, 1H), 8.87 (dd, J = 3.2, 1.9 Hz, 2H), 8.43 (dd, J = 8.8, 0.6 Hz, 1H), 8.36 (dt, J = 6.6, 2.3 Hz, 3H), 8.28 (d, J = 8.6 Hz, 2H), 3.98 (q, J = 7.4 Hz, 2H), 3.05 (q, J = 2.2 Hz, 3H), 1.33 (t, J = 7.4 Hz, 3H). LC-MS: mass calculated for C23H17F6N3O6S3[M]+ 641.57, found 642.1 (M+1). With appropriate modification of the starting materials or intermediates thereof, the procedures as described in the preparation example above were used to obtain further compounds of formula I listed in Table B with their physical data.
[0005] Table BBASF(cyPr: cyclopropyl, Et: ethyl)SEo. R1HPLC-MS RtN RW n R31H-NMR data (δ) (Method) (min) 1H NMR (300 MHz, DMSO-d6) δ 9.48 (d, J = 2.0 Hz, 1H), 8.73 (d, J = 2.1 Hz, 1H), 8.54 (d, J = 1.7 Hz, 1H), 8.30 (d, J = 8.7 Hz, 1H), 8.10 (d, J = 8.6 Hz, 1H), 8.02I.1 (S=O)CF3 Et 2546.3 [M+1] 2.11 N (A) (d, J = 8.2 Hz, 2H), 7.56 (d, J = 8.3 Hz, 2H), 3.97 (q, J = 7.6 Hz, 2H), 1.90 – 1.81 (m, 2H), 1.69 – 1.58 (m, 2H), 1.32 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO-d6) δ 9.47 (d, J = 1.9 Hz, 1H), 8.75 – 8.69 (m, 1H), 8.54 (s, 1H), 8.30 (d, J = 8.699Hz, 1H), 8.10 (d, J = 8.8 Hz, 1H), 7.96 (d, J = 8.1 Hz,I.2 (S=O)CF3 Et 2NH O2562 [M-1] 1.94 (A) 2H), 7.58 (d, J = 8.1 Hz, 2H), 7.10 (s, 1H), 6.39 (s, 1H), 3.98 (q, J = 7.5 Hz, 2H), 1.45 – 1.36 (m, 2H), 1.32 (t, J = 7.3 Hz, 3H), 1.04 (q, J = 3.9 Hz, 2H). 1H NMR (300 MHz, DMSO-d6) δ 9.48 (d, J = 2.1 Hz, 1H), 8.73 (d, J = 2.1 Hz, 1H), 8.55 (s, 1H), 8.3I.3 (S=O)CF3 Et 2O 1 (d, J = 564.3 [M+1] 2.13 8.6 Hz, 1H), 8.11 (d, J = 9.0 Hz, 1H), 8.08 – 8.00 (m, (A) N 2H), 7.45 – 7.37 (m, 2H), 3.97 (q, J = 7.3 Hz, 2H), 1.79 (s, 6H), 1.32 (t, J = 7.4 Hz, 3H).240876WO01
[0006] 1H NMR (300 MHz, DMSO-d6) δ 9.49 (d, J = 2.1 Hz,BASF1H), 8.75 (d, J = 2.1 Hz, 1HSI.4 (S=O)CF3 Et 2O O S ), 8.54 (s, 1H), 8.30 (d, J = OE575.3 [M+1]2.03 8.7 Hz, 1H), 8.11 (dd, J = 9.1, 2.4 Hz, 3H), 7.64 – 7.56 (A)(m, 2H), 3.96 (q, J = 7.3 Hz, 2H), 3.48 (s, 3H), 1.32 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO-d6) δ 9.41 (d, J = 2.1 Hz, 1H), 8.64 (d, J = 2.2 Hz, 1H), 8.52 (s, 1H), 8.29 (d, J =I.5 (S=O)CF3 Et 2O N S572.3 [M+1]1.91 8.9 Hz, 1H), 8.09 (d, J = 8.9 Hz, 1H), 7.87 – 7.79 (m, (A)2H), 7.18 – 7.09 (m, 2H), 3.96 (q, J = 6.9 Hz, 2H), 3.29 (s, 6H), 1.31 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO-d6) δ 9.42 (d, J = 2.1 Hz, O 1H), 8.65 (d, J = 2.1 Hz, 1H), 8.53 (d, J = 1.5 Hz, 1H), 10 8.29 (d, J = 8.6 Hz, 1H), 8.14 – 8.05 (m, 1H), 7.86 (d,0I.6 (S=O)CF3 Et 2N S 614 [M+1] 1.98 O (A) J = 8.6 Hz, 2H), 7.25 – 7.16 (m, 2H), 4.16 – 4.05 (m, 2H), 3.96 (q, J = 8.2, 7.7 Hz, 4H), 3.52 (d, J = 6.0 Hz, 2H), 3.51 – 3.40 (m, 2H), 1.31 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO-d6) δ 9.41 (d, J = 2.1 Hz, 1H), 8.64 (d, J = 2.2 Hz, 1H), 8.52 (d, J = 1.4 Hz, 1H), 8.29 (d, J = 8.6 Hz, 1H), 8.09 (d, J = 8.9 Hz, 1H), 7.81I.7 (S=O)CF3 Et 2N S O624 [M+1] 2.09 (A) (d, J = 8.6 Hz, 2H), 7.13 (d, J = 8.6 Hz, 2H), 3.96 (q, J24= 7.3 Hz, 2H), 2.85 (tt, J = 7.7, 5.0 Hz, 2H), 1.31 (t, J =08767.4 Hz, 3H), 1.27 – 1.14 (m, 4H), 1.14 – 1.02 (m, 4H).WO01
[0007] 1H NMR (300 MHz, DMSO-d6) δ 9.52 (d, J = 2.1 Hz,BASF1H), 8.86 (dd, J = 16.1, 2.3 Hz, 2H), 8.63 (ddd, J = 8.7,SE7.7, 2.7 Hz, 1H), 8.55 (d, J = 1.7 Hz, 1H), 8.31 (dd, J =I.8 (S=O)CF3 Et 2F 500 [M+1] 2.05 N (A) 8.6, 0.6 Hz, 1H), 8.15 – 8.06 (m, 1H), 7.47 (dd, J = 8.7, 2.8 Hz, 1H), 3.95 (q, J = 7.4 Hz, 2H), 1.32 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO-d6) δ 9.33 (dd, J = 2.1, 1.3 F Hz, 1H), 8.70 (dd, J = 2.1, 1.2 Hz, 1H), 8.55 (d, J = 1.7 Hz, 1H), 8.31 (dd, J = 8.6, 0.6 Hz, 1H), 8.16 – 8.06 (m,I.9 (S=O)CF3 Et 2F 517 [M+1] 2.21 (A) 1H), 7.97 (td, J = 8.9, 6.4 Hz, 1H), 7.58 (ddd, J = 11.5, 9.3, 2.6 Hz, 1H), 7.45 – 7.32 (m, 1H), 3.97 (q, J = 7.4 Hz, 2H), 1.31 (t, J = 7.4 Hz, 3H). 110 H NMR (300 MHz, DMSO-d6) δ 9.59 (d, J = 2.1 Hz,11H), 9.38 (dd, J = 2.3, 0.9 Hz, 1H), 8.93 (d, J = 2.1 Hz,I.10 (S=O)CF3 Et 2CN 507 [M+1] 2.03 1H), 8.70 (dd, J = 8.2, 2.3 Hz, 1H), 8.56 (d, J = 1.6 Hz, N (A) 1H), 8.31 (dt, J = 8.2, 0.9 Hz, 2H), 8.11 (d, J = 9.0 Hz, 1H), 3.96 (q, J = 7.4 Hz, 2H), 1.33 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, CDCl3) δ 9.15 (s, 1H), 8.73 (m, 2H), 8.31 (s, 1H), 7.99 (dd, J = 8.2, 2.3 Hz, 1H), 7.96 –I.11 (S=O)CF3 Et 2547.3 [M+1] 2.10 N CN (A) 7.75 (m, 3H), 4.04 (q, J = 7.4 Hz, 2H), 1.95 – 1.73 (m,244H), 1.42 (t, J = 7.4 Hz, 3H).0876WO01
[0008] 1H NMR (300 MHz, DMSO-d6) δ 9.17 (d, J = 1.9 Hz,BA3 O FSF1H), 8.58 – 8.52 (m, 2H), 8.31 (dd, J = 8.7, 0.6 Hz,SFEI.12 (S=O)CF Et 2527 [M+1] 2.07 1H), 8.15 – 8.06 (m, 1H), 6.15 (s, 1H), 4.43 (dt, J = O (A) 14.9, 12.0 Hz, 3H), 4.28 (d, J = 12.0 Hz, 1H), 3.98 (q, J = 7.4 Hz, 2H), 1.28 (t, J = 7.4 Hz, 3H) 1H NMR (300 MHz, DMSO) δ 9.98 (s, 1H), 9.84 (d, J = N O 2.0 Hz, 1H), 9.54 (d, J = 1.4 Hz, 1H), 9.42 (d, J = 1.5 Hz, 1H), 9.15 (d, J = 2.0 Hz, 1H), 8.58 – 8.53 (m, 1H),I.13 (S=O)CF3 Et 2N 584.3 [M+1] 2.01 H2N (B) 8.32 (d, J = 8.6 Hz, 1H), 8.14 – 8.06 (m, 1H), 6.08 (d, J O = 0.9 Hz, 1H), 4.01 (q, J = 7.3 Hz, 2H), 1.43 (s, 6H), 1.33 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, CDCl3) δ 9.58 (d, J = 2.1 Hz, 1H), 10 9.12 (dd, J = 6.5, 1.8 Hz, 2H), 9.00 (d, J = 1.5 Hz, 1H),2I.14 (S=O)CF3 Et 2N 548.3 [M+1] N 2.12 8.44– 8.19 (m, 1H), 8.00 – 7.73 (m, 2H), 4.04 (q, J = CN (B) 7.4 Hz, 2H), 1.86 (m, J = 1.4 Hz, 4H), 1.43 (t, J = 7.5 Hz, 3H). 1H NMR (300 MHz, DMSO) δ 9.47 (d, J = 2.1 Hz, 1H), 8.80 – 8.67 (m, 2H), 8.53 (s, 1H), 8.38 – 8.23 (m, 2I.15 (S=O)CF3 Et 2O H), N 583.3 [M+1] H 1.96 8.10 (d, J = 8.6 Hz, 1H), 7.28 (s, 1H), 7.10 – 6.89 (m, 2 N (B) O 2H), 3.94 (q, J = 7.4 Hz, 2H), 1.64 (s, 6H), 1.31 (t, J =247.4 Hz, 3H).0876WO01
[0009] 1H NMR (300 MHz, DMSO-d6) δ 9.48 (d, J = 2.1 Hz,BASFI.16 SO2CF3 Et 2O 1H), 8.85 (d, J = 1.9 Hz, 1H), 8.74 (d, J = 2.1 Hz, 1H),SE8.41 (dd, J = 8.7, 0.6 Hz, 1H), 8.34 (dd, J = 8.8, 1.9 580.4 [M+1] 2.32 (A) Hz, 1H), 8.08 – 8.02 (m, 2H), 7.45 – 7.37 (m, 2H), 3.97 N (q, J = 7.4 Hz, 2H), 1.79 (s, 6H), 1.32 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO-d6) δ 9.50 (d, J = 2.1 Hz, 1H), 8.85 (d, J = 1.9 Hz, 1H), 8.77 (d, J = 2.1 Hz, 1H),I.17 SO2CF3 Et 2564.3 [M+1] 2.29 8.42 (d, J = 8.7 Hz, 1H), 8.34 (dd, J = 8.7, 1.9 Hz, 1H), N (A) 8.10 – 8.00 (m, 2H), 7.83 – 7.72 (m, 2H), 3.97 (q, J = 7.4 Hz, 2H), 1.77 (s, 6H), 1.33 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO-d6) δ 9.55 (d, J = 2.1 Hz, 10 1H), 8.99 (dd, J = 2.6, 0.7 Hz, 1H), 8.87 (d, J = 2.1 Hz,31H), 8.86 (d, J =I.18 SO2CF3 Et 2O 1.8 Hz, 1H), 8.65 (dd, J = 8.6, 2.6 Hz, 581.2 [M+1] 2.29 N CF3(A) 1H), 8.42 (dd, J = 8.7, 0.7 Hz, 1H), 8.34 (dd, J = 8.9, 1.9 Hz, 1H), 7.56 (dd, J = 8.6, 0.7 Hz, 1H), 3.95 (q, J = 7.4 Hz, 2H), 1.32 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO-d6) δ 9.44 (d, J = 2.1 Hz, 2F3 Et 2O 1H), 8.84 (d, J = 1.9 Hz, 1H), 8.69 (d, J = 2.1 Hz, 1H), 8.41 (d, J = 8.7 Hz, 1H), 8.33 (dd, J = 8.8, 1.9 Hz, 1H),I.19 SO C598.4 [M+1]2O 2.104(A) 7.99 – 7.88 (m, 2H), 7.62 (s, 1H), 7.34 (s, 1H), 7.15 –08 NH72 67.04 (m, 2H), 3.96 (q, J = 7.4 Hz, 2H), 1.52 (s, 6H),WO01.32 (t, J = 7.4 Hz, 3H).1
[0010] 1H NMR (300 MHz, DMSO) δ 9.49 (d, J = 2.1 Hz, 1H),BASF8.85 (d, J = 1.9 Hz, 1H), 8.75 (d, J = 2.1 Hz, 1H), 8.46SEI.20 SO2CF3 Et 2562 [M+1] 2.14 – 8.27 (m, 2H), 8.02 (d, J = 8.4 Hz, 2H), 7.61 – 7.47 N (A) (m, 2H),3.97 (q, J = 7.4 Hz, 2H), 1.92 – 1.77 (m, 2H), 1.74 – 1.50 (m, 2H), 1.38 – 1.20 (m, 3H). 1H NMR (300 MHz, DMSO-d6) δ 9.61 (d, J = 2.1 Hz, 1H), 9.38 (d, J = 2.3 Hz, 1H), 8.95 (d, J = 2.1 Hz, 1H),I.21 SO2CF3 Et 2N CN 523 [M+1] 2.08 8.87 (d, J = 1.9 Hz, 1H), 8.70 (dd, J = 8.2, 2.3 Hz, 1H), (A) 8.43 (d, J = 8.7 Hz, 1H), 8.39 – 8.28 (m, 2H), 3.96 (q, J = 7.4 Hz, 2H), 1.33 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO) δ 9.43 (d, J = 2.1 Hz, 1H),I.22 SO2CF3 Et 2O N S 8.84 (d, J = 1.8 Hz, 1H), 8.66 (d, J = 2.1 Hz, 1H), 8.41 588 [M+1]10 2.07 (d, J = 8.7 Hz, 1H), 8.33 (dd, J = 8.6, 1.9 Hz, 1H), 7.854(A)(d, J = 8.6 Hz, 2H), 7.14 (d, J = 8.5 Hz, 2H), 3.97 (q, J = 7.4 Hz, 2H), 3.31 (s, 6H), 1.32 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO-d6) δ 9.57 (d, J = 2.1 Hz, 1H), 8.87 (dI.23 SO2CF3 Et 2O d, J = 3.2, 1.9 Hz, 2H), 8.43 (dd, J = 8.8, CSF3N 642 [M+1] 2.35 0.6 Hz, 1H), 8.36 (dt, J = 6.6, 2.3 Hz, 3H), 8.28 (d, J = (A) 8.6 Hz, 2H), 3.98 (q, J = 7.4 Hz, 2H), 3.05 (q, J = 2.2 Hz, 3H), 1.33 (t, J = 7.4 Hz, 3H).21 4H NMR (300 MHz, DMSO) δ 9.5008I.24 SO2CF3 Et 2O (d, J = 2.1 Hz, 1H), O S7O 6-1]2.16 8.86 (d, J = 1.9 HW589 [Mz, 1H), 8.77 (d, J = 2.1 Hz, 1H), 8.47O(A) 0– 8.30 (m, 2H), 8.12 (d, J = 8.7 Hz, 2H), 7.60 (d, J =1
[0011] 8.7 Hz, 2H), 3.97 (q, J = 7.4 Hz, 2H), 3.48 (s, 3H),BASF1.32 (t, J = 7.4 Hz, 3H).SE1H NMR (300 MHz, DMSO- d6) δ 9.46 (d, J = 2.1 Hz, 1H), 8.71 (d, J = 2.1 Hz, 1H), 8I.25 SCF3 Et 2O .39 (d, J = 1.8 Hz, 1H), 8.11 (dd, J = 8.6, 0.6 Hz, 1H), 8.08 – 7.98 (m, 2H), 582.3 [M+1] 2.08 (A) 7.92 (dd, J = 8.6, 1.8 Hz, 1H), 7.46 – 7.36 (m, 2H), N 3.96 (q, J = 7.4 Hz, 2H), 1.78 (s, 6H), 1.31 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO- d6) δ 9.48 (d, J = 2.1 Hz, 1H), 8.74 (d, J = 2.1 Hz, 1H), 8.40 (d, J = 1.8 Hz, 1HI.26 SCF3 Et 2O ), S O 559.5 [M+1] 2.25 8.16 – 8.06 (m, 3H), 7.91-7.94 (dd, J = 8.5, 1.8 Hz, O (A) 1H), 7.66 – 7.56 (m, 2H), 3.96 (q, J = 7.4 Hz, 2H), 3.48 10 (s, 3H), 1.32 (t, J = 7.4 Hz, 3H).519F NMR δ -42.46 (3F, S-CF3) 1H NMR (300 MHz, DMSO-d6) δ 9.40 (d, J = 2.1 Hz, O 1H), 8.63 (d, J = 2.1 Hz, 1H), 8.38 (d, J = 1.8 Hz, 1H), 8.10 (d, J = 8.5 Hz, 1H), 7.91 (dd, J = 8.5, 1.8 Hz, 1H),I.27 SCF3 Et 2NS 598 [M+1] O 2.19 (A) 7.88 – 7.81 (m, 2H), 7.23 – 7.16 (m, 2H), 4.16 – 4.05 (m, 2H), 3.96 (td, J = 10.2, 8.6, 5.3 Hz, 4H), 3.61 – 3.42 (m, 4H), 1.31 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO-d6) δ 9.39 (d, J = 2.2 Hz,2408 1H), 8.62 (d, J = 2.1 Hz, 1H), 8.37 (s, 1763 N S O608 H), 8.10 (d, J =I.28 SCF Et 2[M+1] 2.4W8.6 Hz, 1H), 7.95 – 7.88 (m, 1H), 7.80 (d, J = 8.6 Hz,O0(A)12H), 7.13 (d, J = 8.5 Hz, 2H), 3.95 (q, J = 7.4 Hz, 2H),
[0012] 2.91 – 2.79 (m, 2H), 1.31 (t, J = 7.4 Hz, 3H), 1.27 –BASF1.17 (m, 4H), 1.13 – 1.02 (m, 4H).SE1H NMR (300 MHz, DMSO-d6) δ 9.48 (d, J = 2.1 Hz, 1H), 8.73 (dI.29F F F O H N SEt 2ON, J = 2.1 Hz, 1H), 8.66 (s, 1H), 8.30 (dd, J 579 [M+1] 2.17 = 3.6, 1.2 Hz, 2H), 8.09 – 8.00 (m, 2H), 7.46 – 7.36 (A) (m, 2H), 7.12 (s, 1H), 3.97 (q, J = 7.4 Hz, 2H), 1.79 (s, 6H), 1.32 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO- d6) δ 9.50 (d, J = 2.1 Hz, 1H), 8.76 (d, J = 2.1 Hz, 1H), 8.66 (s, 1H),I.30F F F OOH N SEt 2O SO8.37 – 8.26 590.4 [M+1]2.03 (m, 2H), 8.17 – 8.07 (m, 2H), 7.65 – 7.56 (m, 2H), 7.13 (A) (s, 1H), 3.97 (q, J = 7.3 Hz, 2H), 3.48 (s, 3H),1.32 (t, J = 7.4 Hz, 3H). 110 H NMR (300 MHz, DMSO-d6) δ 9.47 (d, J = 2.1 Hz, F61H), 8.73 (d, J = 2.1 Hz, 1H), 8.67 (s, 1H), 8.37 – 8.2 I.31 FF O NSEt 2 O N5 593 [M+1]2.33 (m, 2H), 8.04 (d, J = 8.7 Hz, 2H), 7.41 (d, J = 8.7 Hz, (A)2H), 3.97 (q, J = 7.4 Hz, 2H), 3.07 (d, J = 2.2 Hz, 3H), 1.79 (s, 6H), 1.32 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO- d6): δ 9.49 (d, J = 2.1 Hz, F F F O 1H), 8.76 (d, J = 2.1 Hz, 1H), 8.67 (s, 1H), 8.35 – 8.25 I.32 NSEt 2OO SO 604 [M+1]2.18 (m, 2H), 8.11 (d, J = 8.7 Hz, 2H), 7.60 (d, J = 8.7 Hz,24(A) 2H), 3.97 (q, J = 7.4 Hz, 2H), 3.48 (s, 3H), 3.07 (d, J =08762.3 Hz, 3H), 1.32 (t, J = 7.4 Hz, 3H).WO01
[0013] 1H NMR (300 MHz, DMSO-d6) δ 9.23 (d, J = 1.9 Hz,BASF1H), 8.59 (d, J = 1.9 Hz, 1H), 8.56 – 8.52 (m, 1H), 8SI.33 (S=O)CF3 Et 2 429 [M+1].30 2.06E(d, J = 8.7 Hz, 1H), 8.14 – 8.06 (m, 1H), 4.99 (s, 1H), (A) 3.96 (q, J = 7.3 Hz, 2H), 1.29 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO-d6) δ 9.19 (d, J = 1.9 Hz, 1H), 8.54-8.55 (m, 2H), 8.29 (d, J = 8.6 Hz, 1H), 8.1 (S=O)CF3 Et 2 Si 501 [M4I.34 +1]2.39 (A)– 8.05 (m, 1H), 3.97 (q, J = 7.4 Hz, 2H), 1.29 (t, J = 7.4 Hz, 3H), 0.31 (s, 9H). 1H NMR (300 MHz, DMSO-d6) δ 9.47 (d, J = 2.1 Hz, 1H), 8.85 (d, J = 1.9 Hz, 1H), 8.73 (d, J = 2.1 Hz, 1H), 8.41 (dd, J = 8.7, 0.6 Hz, 1H), 8.34 (dd, J = 8.7, 1.9I.35 SO2CF3 Et 2O NH2582 [M+1] 2.08 (A) Hz, 1H), 8.00 – 7.89 (m, 2H), 7.63 – 7.49 (m, 2H), 7.00 10 (d, J = 7.0 Hz, 2H), 3.97 (q, J = 7.4 Hz, 2H), 1.51 (s,76H), 1.32 (t, J = 7.4 Hz, 3H). 1H NMR (500 MHz, DMSO) δ 9.12 (d, J = 1.9 Hz, 1H), F3 Et 2O 8.52 (dd, J = 11.6, 1.8 Hz, 2H), 8.30 (d, J = 8.6 Hz, 1H), 8.10 (dd, J = 8.6, 1.7 Hz, 1H), 4.26 (dd, J = 11.2,I.36 (S=O)C491 [M+1] 2.05 O (A) 4.9 Hz, 2H), 4.06 (td, J = 12.4, 2.6 Hz, 2H), 3.95 (q, J = 7.4 Hz, 2H), 2.15 – 2.02 (m, 2H), 1.26 (q, J = 7.8 Hz, 3H)240876WO01
[0014] F1H NMR (300 MHz, DMSO-d6) δ 9.29 (q, J = 1.6 Hz,BASF1H), 8.76 – 8.70 (m, 1H), 8.56 (s, 1H), 8.32 (dd, J =SEI.37 (S=O)CF3Et 2 F 535 [M+1] 2.22 8.7, 0.6 Hz, 1H), 8.16 – 8.07 (m, 1H), 7.53 (dd, J = (A) F 9.4, 8.3 Hz, 2H), 3.97 (q, J = 7.4 Hz, 2H), 1.29 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO-d6) δ 9.52 (d, J = 1.9 Hz, O 1H), 8.I.38 (S=O)CF3 Et 2O 79 (d, J = 1.8 Hz, 1H), 8.55 (s, 1H), 8.31 (d, J = N S 600 [M+1] (A) 1.988.7 Hz, 1H), 8.19 (d, J = 8.3 Hz, 2H), 8.09 (t, J = 7.8 Hz, 3H), 3.99 (q, J = 7.4 Hz, 2H), 3.51 (s, 6H), 1.33 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO-d6) δ 9.54 (d, J = 1.7 Hz, OO 1H), 8.84 (m, 2H), 8.43 (d, J = 8.6 Hz, 1H), 8.39 – 8.30 6110I.39 SO2CF3 Et 2N S 6 [M+1] (A) 2.09(m, 1H), 8.19 (d, J = 8.3 Hz, 2H), 8.09 (d, J = 8.6 Hz,82H), 3.99 (q, J = 7.0 Hz, 2H), 3.51 (s, 6H), 1.33 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO-d6) δ 9.31 – 9.23 (m, 1H), F 8.61 (dd, J = 2.0, 1.0 Hz, 1H), 8.54 (d, J = 1.3 Hz, 1H),I.40 (S=O)CF3 Et 2OH 515 [M+1] 2.02 8.30 (d, J = 9.1 Hz, 1H), 8.15 – 8.06 (m, 1H), 7.77 – (A) 7.65 (m, 1H), 6.90 – 6.76 (m, 2H), 3.96 (q, J = 7.4 Hz, 2H), 1.30 (t, J = 7.4 Hz, 3H).241H NMR (300 MHz, DMSO-d6) δ 8.75 (d, J = 2.808 S=O)CF3 Et 2F Hz,762.13 1H), 8.43 (d, J = 1.3 Hz, 1H), 8WI.41 ( N 536 [M+1].21 (d, J = 9.1 Hz, 1H), F (A)O08.03 (dd, J = 8.6, 1.4 Hz, 1H), 7.76 (d, J = 2.8 Hz, 1H),1
[0015] 3.94 (q, J = 7.4 Hz, 2H), 3.73 – 3.59 (m, 4H), 2.42 –BASF2.27 (m, 4H), 1.29 (t, J = 7.4 Hz, 3H).SE1H NMR (300 MHz, DMSO-d6) δ 9.39 – 9.34 (m, 1H), F 3 O 8.75 – 8.70 (m, 1H), 8.55 (d, J = 1.1 Hz, 1H), 8.31 (d, OOJ = 9.2 Hz, 1H), 8.11 (dd, J = 9.1, 1.3 Hz, 1H), 8.I.42 (S=O)CF Et 2S 02 (t, 593 [M+1] 2.08 (A) J = 8.8 Hz, 1H), 7.64 (dd, J = 11.2, 2.4 Hz, 1H), 7.48 (dd, J = 9.0, 2.5 Hz, 1H), 3.97 (q, J = 7.4 Hz, 2H), 3.52 (s, 3H), 1.31 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO-d6) δ 9.43 (d, J = 2.1 Hz, 1H), 8.67 (d, J = 2.1 Hz, 1H), 8.58 – 8.49 (m, 1H), 8.29 (d, J = 8.7 Hz, 1H), 8.10 (d, J = 8.7 Hz, 1H), 7.96 (d, JI.43 (S=O)CF3 Et 2O 537 [M+1] 2.18 (A) = 8.8 Hz, 2H), 7.28 (d, J = 8.8 Hz, 2H), 4.04 – 3.89 (m, 10 3H), 1.32 (t, J = 7.4 Hz, 3H), 0.92 – 0.80 (m, 2H), 0.769– 0.66 (m, 2H). 1H NMR (300 MHz, DMSO-d6) δ 9.39 – 9.33 (m, 1H), 8.77 – 8.71 (m, 1H), 8.55 (d, J = 1.5 Hz, 1H), 8.31 (d, J = 9.1 Hz, 1H), 8.11 (dd, J = 8.8, 1.4 Hz, 1H), 8.01I.44 (S=O)CF3 Et 2F O (t, O SO619 [M+1] 2.09 J = 8.7 Hz, 1H), 7.63 (dd, J = 11.1, 2.4 Hz, 1H), 7.49 (A) (dd, J = 8.7, 2.9 Hz, 1H), 3.97 (q, J = 7.4 Hz, 2H), 3.26 – 3.15 (m, 1H), 1.37 – 1.20 (m, 5H), 1.11 (dt, J = 8.4,244.3 Hz, 2H).0876WO01
[0016] 1H NMR (300 MHz, DMSO-d6) δ 9.49 (d, J = 2.1 Hz,BASF1H), 8.76 (d, J = 2.1 Hz, 1H), 8.54 (d, J = 1.5 Hz, 1H),SE8.30 (d, J = 9.1 Hz, 1H), 8.15 – 8.05 (m, 3H),I.45 (S=O)CF3Et 2O O S 7.65 – O 601 [M+1] 2.01 (A) 7.57 (m, 2H), 3.97 (q, J = 7.4 Hz, 2H), 3.22 – 3.11 (m, 1H), 1.32 (t, J = 7.4 Hz, 3H), 1.26 – 1.19 (m, 2H), 1.13 – 1.03 (m, 2H). 1H NMR (300 MHz, DMSO-d6) δ 9.34 – 9.28 (m, 1H), F 8.65 (d, J = 2.7 Hz, 1H), 8.54 (d, J = 1.0 Hz, 1H), 8.30 (d, J = 8.9 Hz, 1H), 8.14 – 8.0 S=O)CF3 Et 2584 [M 7 (m, 1H), 7.81 (t, J =I.46 (+1] 1.97 NH O2(A) 8.9 Hz, 1H), 7.72 – 7.62 (m, 1H), 7.39 (s, 1H), 6.95 (d, J = 11.1 Hz, 2H), 3.96 (q, J = 7.3 Hz, 2H), 1.30 (t, J = 7.4 Hz, 3H). 111 H NMR (300 MHz, DMSO) δ 9.34 (dd, J = 2.1, 1.4 Hz,0F 1H), 8.70 (dd, J = 2.0, 1.2 Hz, 1H), 8.55 (s, 1H), 8.31 (dd, J = 8. O N 7, 0.6 Hz, 1H), 8.11 (d, J = 8.8 Hz, 1H), 7.93I.47 (S=O)CF3 Et 2582.2 [M+1] 2.25 (A) (t, J = 9.1 Hz, 1H), 7.38 – 7.25 (m, 2H), 3.97 (q, J = 7.4 Hz, 2H), 1.81 (s, 6H), 1.31 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO) δ 9.51 (d, J = 2.1 Hz, 1H), 8.78 (d, J = 2.1 Hz, 1H), 8.55 (s, 1H), 8.31 (dd, J = 8.7,I.48 (S=O)CF3 Et 2O O S 575.2 [M+1] 2.08240.6 Hz, 1H), 8.11 (d, J = 8.8 Hz, 1H), 8.06 – 7.98 (m,08 O (A)762H), 7.74 (t, J = 8.3 Hz, 1H), 7.58 (dd, J = 2.4, 0.9 Hz,WO01
[0017] 1H), 3.97 (q, J = 7.4 Hz, 2H), 3.50 (s, 3H), 1.33 (t, J =BASF7.4 Hz, 3H)SEO1H NMR (300 MHz, DMSO) δ 9.81 (d, J = 2.0 Hz, 1H), 9.18 (d, J = 2.0 Hz, 1H), 8.88 (d, J = 3.4 Hz, 1H), 8.60I.49 (S=O)CF3 Et 2NOS O 576.2 [M+1] 2.05 – 8.51 (m, 2H), 8.32 (d, J = 9.3 Hz, 1H), 8.12 (m, 2H), (A) 4.00 (q, J = 7.4 Hz, 2H), 3.58 (s, 3H), 1.32 (t, J = 7.4 Hz, 3H). 1H NMR (500 MHz, DMSO) δ 9.81 (d, J = 2.0 Hz, 1H), OO9.19 (d, J = 2.1 Hz, 1H), 8.89 (dd, J = 2.8, 0.6 Hz, 1H), 8.59 – 8.47 (m, 2H), 8.32 (dd 3t 2N O S , J = 8.6, 0.6 Hz, 1H),I.50 (S=O)CF E602.2 [M+1] 2.13 (A) 8.13 (ddd, J = 10.2, 8.6, 2.3 Hz, 2H), 4.01 (q, J = 7.4 Hz, 2H), 3.26 (tt, J = 7.9, 4.7 Hz, 1H), 1.33 (t, J = 7.4 11 Hz, 3H), 1.29 – 1.26 (m, 2H), 1.14 – 1.04 (m, 2H).11H NMR (500 MHz, DMSO) δ 9.52 (d, J = 2.1 Hz, 1H), OO8.80 (d, J = 2.1 Hz, 1H), 8.55 (d, J = 1.7 Hz, 1H), 8.31 O)CF3 Et 2S (d, J = 8.5 Hz, 1H), 8.23 (dd, J = 11.3, 2.3 Hz, 1H),I.51 (S= O 593.2 [M+1]2.10 (A) 8.11 (dd, J = 8.6, 1.7 Hz, 1H), 7.95 (dt, J = 8.5, 1.5 Hz, F 1H), 7.77 (t, J = 8.3 Hz, 1H), 3.96 (q, J = 7.4 Hz, 2H), 3.59 (s, 3H), 1.33 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO) δ 9.93 (d, J = 1.9 Hz, 1HI.53 (S=O)CF3 Et 2NOSO),2402.0 9.34 (d, J = 2.0 Hz, 1H), 9.20 (s, 2H), 8.57 (d, J = 1.6 87N O 577 [M+1] 66(A) Hz, 1H), 8.33 (dd, J = 8.6, 0.6 Hz, 1H), 8.12 (d, J = 8.3WO01
[0018] Hz, 1H), 4.05 (q, J = 7.4 Hz, 3H), 3.65 (s, 3H), 1.42 –BASF1.27 (m, 2H).SEF1H NMR (500 MHz, DMSO-d6) δ 9.53 (d, J = 2.1 Hz, 1H), 8.82 (d, J = 2.1 Hz, 1H), 8.55 (s, 1H), 8.31 (d, J = 8.7 Hz, 1H), 8.11 (d, J = 9.7 Hz, 1H), 8.03 (dt, J = 9.6,I.54 (S=O)CF3 Et 2O 593.2 [M+1] 2.12 O S O (A) 1.9 Hz, 1H), 7.91 (s, 1H), 7.56 (dt, J = 9.1, 2.1 Hz, 1H), 3.96 (q, J = 7.4 Hz, 2H), 3.54 (s, 3H), 1.34 (t, J = 7.4 Hz, 3H) 1H NMR (300 MHz, DMSO) δ 9.48 (d, J = 2.1 Hz, 1H), O 8.75 (d, J = 2.1 Hz, 1H), 8.54 (d, J = 1.7 Hz, 1H), 8.30 (dd, J = 8.6, 0.6 Hz, 1H), 8.1 =O)CF3 Et 2 O3 – 8.05 (m, 3H), 7.58 –I.55 (S OS615.3 [M+1]2.22 7.50 (m, 2H), 4.46 (q, J = 8.3 Hz, 1H), 3.96 (q, J = 7.4 (A)11 Hz, 2H), 2.48 – 2.38 (m, 4H), 2.12 – 1.95 (m, 2H), 1.322(t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO) δ 9.48 (d, J = 2.1 Hz, 1H), 8.75 (d, J = 2.1 Hz 3OOSO, 1H), 8.54 (d, J = 1.7 Hz, 1H), 8.30 (dd, J = 8.7, 0.6 Hz, 1H), 8.10 (dd, J = 9.2, 2.5 Hz,I.56 (S=O)CF Et 2 603.2 [M+1]2.19 3H), 7.60 – 7.52 (m, 2H), 3.97 (q, J = 7.4 Hz, 2H), 3.83 (A)(p, J = 6.8 Hz, 1H), 1.48 (d, J = 6.8 Hz, 6H), 1.32 (t, J24= 7.4 Hz, 3H)0876WO01
[0019] 1H NMR (500 MHz, DMSO) δ 9.49 (d, J = 2.1 Hz, 1H),BASF8.76 (d, J = 2.1 Hz, 1H), 8.55 (d, J = 1.7 Hz, 1H), 8.31SO E(d, J = 8.7 Hz, 1H), 8.1 3O1 (dd, J = 8.9, 2.3 Hz, 3H), 7.60I.57 (S=O)CF Et 2 OS603.2 [M+1]2.2 – 7.56 (m, 2H), 3.97 (q, J = 7.4 Hz, 2H), 3.64 – 3.56 (A) (m, 2H), 1.95 – 1.85 (m, 2H), 1.33 (t, J = 7.4 Hz, 3H), 1.07 (t, J = 7.4 Hz, 3H) 1H NMR (300 MHz, DMSO) δ 9.50 (d, J = 2.1 Hz, 1H), 8.85 (d, J = 1.9 Hz 2OSO, 1H), 8.77 (d, J = 2.1 Hz, 1H), 8.42 (S=O) CF (dd, J = 8.7, 0.6 Hz, 1H), 8.34 (dd, J = 8.7, 1.9 Hz, I.58Et 23O 631.3 [M+1]2.3 (A) 1H), 8.14 – 8.04 (m, 2H), 7.59 – 7.50 (m, 2H), 4.48 (p, J = 8.2 Hz, 1H), 3.97 (q, J = 7.4 Hz, 2H), 2.49 – 2.38 1 (m, 4H), 2.09 – 1.95 (m, 2H), 1.33 (t, J = 7.4 Hz, 3H). 131H NMR (300 MHz, DMSO) δ 9.48 (d, J = 2.1 Hz, 1H), 8.75 (d, J = 2.1 Hz, 1H), 8.54 (d, J = 1.7 Hz, 1H), 8.30 O (dd, J O SO= 8.7, 0.6 Hz, 1H), 8.11– 8.09 (m, 3H), 7.61 – 7.51 (m, 2H), 3.96 (q, J = 7.4 Hz, 2H), 3.71 – 3.55 (m,I.59 (S=O)CF3 Et 2 643.3 [M+1]2.35 (A) 1H), 2.30 – 2.19 (m, 2H), 1.88-1.82 (m, 2H), 1.72 – 1.52 (m, 4H), 1.50 – 1.33 (m, 2H), 1.32 (t, J = 7.4 Hz, 3H).240876WO01
[0020] 1H NMR (500 MHz, DMSO) δ 9.49 (d, J = 2.1 Hz, 1H),BASFO8.76 (d, J = 2.1 Hz, 1H), 8.55 (d, J = 1.7 Hz, 1H), 8.31SE(d, J = 8.6 Hz, 1H), 8.11 (dd, J = 8.8, 2.2 Hz, 3H), 3OOS 7.61I.60 (S=O)CF Et 2 589.2 [M+1]2.13 – 7.55 (m, 2H), 3.97 (q, J = 7.4 Hz, 2H), 3.62 (q, J = (A)7.3 Hz, 2H), 1.43 (t, J = 7.3 Hz, 3H), 1.33 (t, J = 7.4 Hz, 3H). 1H NMR (500 MHz, DMSO) δ 9.50 (d, J = 2.1 Hz, 1H), 8.86 (d, J = 1.9 Hz, 1H), 8.77 (d, J = 2.1 Hz, 1H), 8 O)2CFO.42 (S=O(d, J = 8.7 Hz, 1H), 8.35 (dd, J = 8.8, 1.9 Hz, 1H), 8.13 I.61Et 23OS619.2 [M+1]2.28 (A)– 8.08 (m, 2H), 7.59 – 7.54 (m, 2H), 3.97 (q, J = 7.5 Hz, 2H), 3.83 (hept, J = 6.8 Hz, 1H), 1.48 (d, J = 6.8 1 Hz, 6H), 1.33 (t, J = 7.4 Hz, 3H). 141H NMR (500 MHz, DMSO) δ 9.50 (d, J = 2.1 Hz, 1H), 8.86 (d, J = 1.9 Hz, 1H), 8.78 (d, J = 2.1 Hz, 1H), 8.42 (S=O)2CFO O(d, J = 8.7 Hz, 1H), 8.35 (dd, J = 8.8, 2.0 Hz, 1H), 8.1 I.62t 23OS 4 E619.2 [M+1]2.29 (A) – 8.09 (m, 2H), 7.61 – 7.56 (m, 2H), 3.97 (q, J = 7.5 Hz, 2H), 3.64 – 3.57 (m, 2H), 1.94 – 1.84 (m, 2H), 1.33 (t, J = 7.4 Hz, 3H), 1.07 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO) δ 9.50 (d, J = 2.1 Hz, 1 (S=O)2CFO OH),248.85 (d, J = 1.9 Hz, 1H), 8.77 (d, J = 2.1 H08 3Oz, 1H), 8.42 I.63Et 2S659.3 [M+1]2.4376(A) (dd, J = 8.8, 0.6 Hz, 1H), 8.34 (dd, J = 8.8, 1.9 Hz,WO01H), 8.14 – 8.07 (m, 2H), 7.59 – 7.52 (m, 2H), 3.97 (q,1
[0021] J = 7.4 Hz, 2H), 3.70 – 3.56 (m, 1H), 2.27 – 2.23 (m,BASF2H), 1.88-1.83 (m, 2H), 1.72 – 1.54 (m, 4H), 1.48 –SE1.36 (m, 2H), 1.33 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO) δ 9.48 (d, J = 2.1 Hz, 1H), OO8.76 (d, J = 2.1 Hz, 1H), 8.39 (d, J = 1.8 Hz, 1H), 8.17 O S F – 8.10 (m, 3H), 7.97 – 7.90 (m, 1H), 7.79 (s, 1H), 7.68I.64 SCF3 Et 2F596 [M+2]2.37 (A) – 7.63 (m, 2H), 3.95 (q, J = 7.4 Hz, 2H), 1.32 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO) δ 9.47 (d, J = 2.1 Hz, 1H), O 8.74 (d, J = 2.1 Hz, 1H), 8.39 (d, J = 1.8 Hz, 1H), 8.16 – 8.03 (m, 3H), 7.92 (dd, J = 8.6, 1.8 Hz, 1H), 7.59I.65 SCF3 Et 2 OOS – 1 627 [M+1]1 2.56 7.51 (m, 2H), 3.97 (p, J = 7.7 Hz, 2H), 3.63 (tt, J =5(A) 11.8, 3.4 Hz, 1H), 2.25 (d, J = 12.6 Hz, 2H), 1.85 (d, J = 13.0 Hz, 2H), 1.72 – 1.52 (m, 4H), 1.49 – 1.12 (m, 5H). 1H NMR (300 MHz, DMSO) δ 9.47 (d, J = 2.1 Hz 6SCF3 Et 2 O O, 1H), 8.74 (d, J = 2.1 Hz, 1H), 8.39 (d, J = 1.8 Hz, 1H), 8.16I.6 OS587 [M+1]2.39 – 8.03 (m, 3H), 7.92 (dd, J = 8.4, 1.9 Hz, 1H), 7.61 – (A)7.51 (m, 2H), 3.96 (q, J = 7.4 Hz, 2H), 3.81 (h, J = 6.824Hz, 1H), 1.48 (d, J = 6.8 Hz, 6H), 1.37 – 1.19 (m, 3H).0876WO01
[0022] 1H NMR (300 MHz, DMSO) δ 9.80 (d, J = 2.0 Hz, 1H),BASFOSO9.17 (d, J = 2.0 Hz, 1H), 8.86 (dd, J = 2.8, 0.6 Hz, 1H),SE8.59 – 8.48 (m, 2H), 8.32 (dd, J = 8.7, 0.6 Hz, 1H),I.67 (S=O)CF3 Et 2O 590 [M+1] 2.1 8.16 – 8.06 (m, 2H), 4.00 (q, J = 7.4 Hz, 2H), 3.72 (q, N (A) J = 7.3 Hz, 2H), 1.45 (t, J = 7.3 Hz, 3H), 1.32 (t, J = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO) δ 9.48 (d, J = 2.1 Hz, 1H), 8.75 (d, J = 2.1 Hz, 1H), 8.54 (d, J = 1.7 Hz, 1H), 8.30 O (dd, J = 8.6, 0.6 Hz, 1H), 8.10 (dd, J = 9. 3OOS 2, 2.5 Hz, 3H),I.68 (S=O)CF Et 2 629.3 [M+1]2.27 7.62 – 7.51 (m, 2H), 4.16 – 4.05 (m, 1H), 4.05 – 3.90 (A) (m, 2H), 2.23 – 1.96 (m, 4H), 1.82 – 1.58 (m, 4H), 1.32 (t, J = 7.4 Hz, 3H). 1161H NMR (300 MHz, DMSO) δ 9.49 (d, J = 2.1 Hz, 1H), O 8.77 (d, J = 2.1 Hz, 1H), 8.54 (d, J = 1.7 Hz, 1H), 8.30 SOF (dd, J = 8.6, 0.6 Hz, 1H), 8.21 – 8.06 (m, 3H), 7.71 –I.69 (S=O)CF3 Et 2 OF611.2 [M+1]2.17 (A) 7.59 (m, 2H), 3.96 (q, J = 7.4 Hz, 2H), 1.32 (t, J = 7.4 Hz, 3H). 240876WO01
[0023] Cl1H NMR (300 MHz, DMSO) δ 9.74 (d, J = 2.0 Hz, 1H),BASF9.03 (d, J = 2.1 Hz, 1H), 8.56 (d, J = 1.7 Hz, 1H), 8.32SEI.70 (S=O)CF3 Et 2N 547.2 [M+1] 1.97 (dd, J = 8.6, 0.6 Hz, 1H), 8.12 (d, J = 8.9 Hz, 1H), 7.57 N (A) (s, 1H), 4.01 (q, J = 7.4 Hz, 2H), 3.63 (s, 3H), 1.32 (t, J O = 7.4 Hz, 3H). 1H NMR (300 MHz, DMSO) δ 9.49 (d, J = 2.1 Hz, 1H), OO F 8.78 (d, J = 2.1 Hz, 1H), 8.54 (d, J = 1.7 Hz, 1H), 8.31 (dd, J = 8.7, 0.6 Hz, 1H), 8.19 (dd, J = 7.3, 2.3 Hz,I.71 (S=O)CF3 Et 2 SO 593.2 [M+1] 1.35 (A) 1H), 8.14 – 8.01 (m, 2H), 7.73 (dd, J = 10.1, 8.7 Hz, 1H), 3.95 (q, J = 7.4 Hz, 2H), 3.61 (s, 3H), 1.33 (t, J = 7.4 Hz, 3H). 1H NMR (500 MHz, DMSO) δ 9.49 (d, J = 2.1 Hz, 1H),11 8.77 (d, J = 2.1 Hz, 1H), 8.55 (d, J = 1.7 Hz, 1H), 8.317F (d, J = 8.6 Hz, 1H), 8.19 (dd, J = 7.2, 2.4 Hz, 1H), 8.11 O (dd, J = 8.7, 1.7 Hz, 1H), 8.06 (ddd, J = 8.6, 4.4, 2.3I.72 (S=O)CF3 Et 2 OSO 619.2 [M+1]2.17 (A) Hz, 1H), 7.74 (dd, J = 10.0, 8.7 Hz, 1H), 3.96 (q, J = 7.4 Hz, 2H), 3.28 (tt, J = 7.9, 4.6 Hz, 1H), 1.33 (t, J = 7.4 Hz, 3H), 1.28 (dt, J = 6.9, 3.4 Hz, 2H), 1.15 (ddd, J = 7.0, 5.0, 2.1 Hz, 2H). FO O1H NMR (500 MHz, DMSO) δ 9.52 (d, J = 2.1 Hz, 1H),248.81 (d, J = 2.1 Hz, 1H), 8.55 (d, J = 1.7 Hz08 O , 1H), 8.3I.73 (S=O)CF3 Et 2S 17619.2 [M+1]2.176(d, J = 8.6 Hz, 1H), 8.23 (dW(A)d, J = 11.3, 2.3 Hz, 1H),O08.11 (dd, J = 8.6, 1.7 Hz, 1H), 7.97 – 7.91 (m, 1H),1
[0024] 7.76 (t, J = 8.3 Hz, 1H), 3.96 (q, J = 7.4 Hz, 2H), 3.25BASF(tt, J = 7.9, 4.7 Hz, 1H), 1.33 (t, J = 7.4 Hz, 3H), 1.30 –SE1.26 (m, 2H), 1.16 – 1.11 (m, 2H). 1H NMR (500 MHz, DMSO) δ 9.48 (d, J = 2.1 Hz, 1H), O 8.74 (d, J = 2.1 Hz, 1H), 8.40 (d, J = SO1.8 Hz, 1H), 8.11 (dd, J = 9.5, 8.6 Hz, 3H), 7.93 (dd, J = 8.5, 1.9 Hz,I.74 SCF3 Et 2 O 587 [M+1]2.4 (A) 1H), 7.61 – 7.54 (m, 2H), 3.96...
Claims
127 Claims1. A compound of formula (I)whereinR1is S(O)m-C1-C4-alkyl, S(O)m-C3-C6-cycloalkyl, S(O)m-C3-C6-cycloalkyl-C1-C4-alkyl, which are unsubstituted or halogenated; S(O)(=NH)RM, S(O)(=NRM)RM; C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, -O-C3-C6-cycloalkyl, all of which are unsubstituted, partially halogenated or fully halogenated; RW is C1-C4-alkyl, cyclopropyl, C3-C6-cycloalkyl-C1-C4-alkyl;m is 0, 1 or 2;n is 0, 1 or 2;R3is phenyl substituted with (a) one R4, or (b) substituted with one R4and one halogen, or (c) substituted with up to 5 halogens; or a six-membered saturated, partially unsaturated, or fully unsaturated heterocyclicring or ring system, wherein said heterocyclic ring or ring system comprises one, two or three, same or different heteroatoms O or N which may be unsubstituted or substituted with C1-C4-alkyl, and is substituted with (a) one R4, or (b) two halogens, or (c) one R4and one halogen; or a 1,3-benzodioxole which is unsubstituted or halogenated; or C1-C4-alkynyl, which is unsubstituted or substituted with Si(R5)3; wherein R5 is C1-C4-alkyl; R4is C(RM)2-(CN), CHRM-CN, C(RM)2-(CONH2), CHRM-(CONH2), C(RM)2-(CSNH2), CHRM- (CSNH2), 1-cyano-C3-C6-cycloalkyl, 1-C3-C6-cycloalkyl-carboxamide, 1-C3-C6- cycloalkyl-thiocarboxamide, O-CH2-CN, O-CHRM-CN, O-C(CN)(RM)2, O-C(CONH2)(RM)2, O-C(CSNH2)(RM)2,O-1-cyano- C3-C6-cycloalkyl, O- C(CONH2)- C3-C6-cycloalkyl, O- C(CSNH2)- C3-C6- cycloalkyl; O-S(O)2-RM; C1-C3-alkoxy, which is unsubstituted or partially or fully halogenated; C3-C6-cycloalkyl- C1-C3-alkoxy which is unsubstituted or partially or fully halogenated, C3-C6-cycloalkoxywhich is unsubstituted or partially or fully halogenated; S(O)(=NRM)RM, S(O)(=NH)RM, N=S(O)(RM)2, CO-N=SO(RM)2, halogen, cyano, (=O), C(=O)H, C(=O)RM, difluoromethylen,128 each RMis independently C1-C3-alkyl which is unsubstituted or partially or fully halogenated; or C3-C6-cycloalkyl, or C3-C6-cycloalkyl in which at least one C is replaced by a heteroatom; or in case of two adjacent substituents RM, the substituents may form a ring together by aC2-C6-alkyl bridge, which is unsubstituted or partly or fully halogenated and in whichone or more carbon atoms may be replaced by O or N; and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof, provided that if R1is S(O)(=NH)RMor S(O)(=NRM)RM, R3is not 5-chloro-pyrimidin-2-yl or 5-cyano-pyrimidin-2-yl2. The compound of formula (I) according to claim 1, whereinR1is S(O)m-C1-C4-alkyl, S(O)m-C3-C6-cycloalkyl, S(O)m-C3-C6-cycloalkyl-C1-C4-alkyl, which are unsubstituted or halogenated.
3. The compound of formula (I) according to claim 1 or 2, which is compound I*:wherein Xis C, O;Y is C, N;Z is C, N, O;M is C, N;A is C;wherein any hetero atoms may be unsubstituted or substituted with C1-C4-alkyl, and one C atom is substituted with R4.
4. The compound of formula (I) according to any of claims 1 to 3, in which R3 is phenylsubstituted with one R4, or substituted with 2 or 3 halogens, preferably compound I.A:1295. The compound of formula (I) according to any of claims 1 to 4, in which R3 is one of thefollowing heterocycles:R3.
116. The compound of formula (I) according to any of claims 1 to 5, whereinR4 is C(RM)2-(CN), CHRM-CN, C(RM)2-(CONH2), CHRM-(CONH2), C(RM)2-(CSNH2), CHRM-(CSNH2), 1-cyano-C3-C6-cycloalkyl, 1-C3-C6-cycloalkyl-carboxamide, 1-C3-C6- cycloalkyl-thiocarboxamide, O-CH2-CN, O-CHRM-CN, O-C(CN)(RM)2, O-C(CONH2)(RM)2, O-C(CSNH2)(RM)2, O-S(O)2-RM; C1-C3-alkoxy, which is unsubstituted or partially or fully halogenated; C3-C6-cycloalkyl-C1-C3-alkoxy, S(O)(=NRM)RM, S(O)(=NH)RM, N=S(O)(RM)2, CO-N=SO(RM)2, halogen, cyano, (=O), C(=O)H, C(=O)RM, difluoromethylen, preferablyR4is C(RM)2-(CN), C(RM)2-(CONH2), 1-cyano-C3-C6-cycloalkyl, 1-C3-C6-cycloalkyl- carboxamide, O-C(CN)(RM)2, O-C(CONH2)(RM)2, O-S(O)2-RM; C1-C3-alkoxy, which is fully halogenated; S(O)(=NRM)RM, S(O)(=NH)RM, N=S(O)(RM)2, halogen, cyano, (=O), C(=O)H, C(=O)RM, difluoromethylen. preferablyR4is C(RM)2-(CN), C(RM)2-(CONH2), 1-cyano-C3-C6-cycloalkyl, 1-C3-C6-cycloalkyl- carboxamide, O-C(CN)(RM)2, O-C(CONH2)(RM)2, O-S(O)2-RM; C1-C3-alkoxy, which is fully halogenated; S(O)(=NRM)RM, S(O)(=NH)RM, N=S(O)(RM)2, (=O), C(=O)H, C(=O)RM, difluoromethylen.1307. The compound of formula (I) according to any of claims 1 to 6, whereineach RMis independently C1-C3-alkyl, which is unsubstituted or partially or fully halogenated; or C3-C6-cycloalkyl, preferably methyl, trifluoromethyl or cyclopropyl; or in case of two adjacent substituents RM, the substituents may form a ring together bya C2-C6-alkyl bridge, which is unsubstituted or partly or fully halogenated and in which one or more carbon atoms may be replaced by O or N, preferably an ether bridge.
8. The compound of formula (I) according to any of claims 1 to 7, whereinR4 is C(CH3)2-(CN), C(CH3)2-(CONH2), 1-cyano-cyclopropyl, 1-cyclopropyl-carboxamide, O-C(CN)(CH3)2, O-C(CONH2)(CH3)2, O-S(O)2-CH3, O-S(O)2-RM, preferably O-S(O)2- CHF2, O-S(O)2-ethyl, O-S(O)2-propyl, O-S(O)2-cyclopropyl, O-S(O)2-cyclobutyl, O- S(O)2-cyclopentyl, O-S(O)2-cyclohexyl, O-S(O)2-morpholinyl; C1-C3-alkoxy, which is fully halogenated (preferably trifluoromethoxy), S(O)(=NRM)RM, preferably S(O)(=NCH3)CH3, S(O)(=NH)RM, preferably S(O)(=NH)CH3, N=S(O)(CH3)2,halogen, or cyano.
9. The compound of formula (I) according to any of claims 1 to 8, whereinR4is C(CH3)2-(CN), C(CH3)2-(CONH2), 1-cyano-cyclopropyl, 1-cyclopropyl-carboxamide, O- C(CN)(CH3)2, O-C(CONH2)(CH3)2, halogen, or cyano.
10. The compound of formula (I) according to any of claims 1 to 9, whereinR3is C1-C4-alkynyl, which is unsubstituted or substituted with Si(R5)3; wherein R5is C1-C4- alkyl; preferably R3 is propargyl which is unsubstituted or substituted with SiMe3; orR3is phenyl or a six-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring system comprises one, two or three, same or different heteroatoms O or N which may be unsubstituted or substituted with C1-C4-alkyl, wherein the phenyl or heterocyclic ring or ring system is substituted with one R4, wherein R4 is O-S(O)2-RM, C(RM)2-(CN), 1-cyano-C3-C6-cycloalkyl, O-CH2-CN, O-CHRM-CN, O-C(CN)(RM)2, O-C(CONH2)(RM)2, N=S(O)(RM)2, halogen, cyano; or a 1,3-benzodioxole which is unsubstituted or halogenated.
11. The compound of formula (I) according to any of claims 1 or 3 to 10, whereinR1is (S=O)-CF3, SO2-CF3, SCF3, S(O)(=NH)CF3or S(O)(=NCH3)CF3, and RWis ethyl, n is 2, or according to claim 2, wherein R1is (S=O)-CF3, SO2-CF3, SCF3and RWis ethyl, n is 2, preferably wherein R1is (S=O)-CF3, SO2-CF3, SCF3, and RWis ethyl, n is 2.13112. A composition comprising the compound of formula (I), as defined in any of claims 1 to 11,an N-oxide or an agriculturally acceptable salt thereof and at least one inert liquid and / or solid carrier.
13. A method for combating or controlling invertebrate pests, which method comprisescontacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound of the formula (I) according to any of claims 1 to 11 or the composition according to claim 12.
14. A method for protecting growing plants from attack or infestation by invertebrate pests,which method comprises contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one compound of the formula (I), according to any of the claims 1 to 11 or the composition according to claim 12.
15. Seed comprising a compound of the formula (I), as defined in any of claims 1 to 11, or thecomposition as defined in claim 12, in an amount of from 0.1 g to 10 kg per 100 kg of seed.
16. A method for protection of plant propagation material comprising contacting the plantpropagation material with the pesticidal compound of formula (I) as defined in any of claims1 to 11 in an amount of from 0.1 g to 10 kg per 100 kg of plant propagation material.
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