Pesticidal compounds and uses thereof

Abstract

The present invention is in the field of agricultural or veterinary applications and relates to compounds of formula (I), as described herein, that have pesticidal activity and uses thereof as well as methods of use.

Description

[0001] BASF SE 240902W001

[0002] B 19223 WO

[0003] 1

[0004] PESTICIDAL COMPOUNDS AND USES THEREOF

[0005] Field of the invention

[0006] The present invention is in the field of agricultural or veterinary applications and relates to compounds that have pesticidal activity and uses thereof as well as methods of use, as described herein.

[0007] Background of the invention

[0008] Invertebrate pests and in particular insects, arachnids and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, thereby causing large economic loss to the food supply and to property. Accordingly, agents for combating invertebrate pests are widely used in this field.

[0009] 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 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.

[0010] Heterocyclic compounds that show pesticidal activity are known in the art, for example from international patent publication W02021011722.

[0011] It is however an object of the present invention to identify and provide further compounds, which exhibit a high pesticidal activity and have a broad activity spectrum against invertebrate pests.

[0012] Summary of the invention

[0013] It has been found that these objects can be achieved by substituted bicyclic compounds of formula I that have a 1 ,2,4-triazol-3-yl-pyrazin-2-yl core structure, as depicted and defined below, including their stereoisomers, their salts, in particular their agriculturally or veterinarily acceptable salts, their tautomers and their N-oxides.

[0014] In a first aspect, the present invention relates to the compounds of formula I, wherein

[0015] B1is CRB1;

[0016] B2is CRB2;

[0017] RB1and RB2independently of each other are H, halogen, N3, OH, CN, NO2, -SON, -SF5, Ci-Ce-alkyl, C1- Ce-alkoxy, C2-Ce-alkenyl, tri-Ci-Ce-alkylsilyl, C2-Ce-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-Ce- alkoxy-Ci-C4-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, C1-C4- 2 alkyl-Cs-Ce-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

[0018] C(=O)-ORa, NRbRc, Ci-C6-alkylene-NRbRc, O-Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, NH-Ci- C6-alkylene-NRbRc, C(=O)-NRbRc, C(=O)-Rd, SO2NRbRc, or S(=O)mRe, phenyl, phenoxy, phenylcarbonyl, phenylthio, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with one or more Rf;

[0019] R2and R3are H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-alkoxy-Ci-C4-alkyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(=O)-ORa, Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, C(=O)-NRbRc, C(=O)-Rd, SO2NRbRc, S(=O)mRe, phenyl, -CH2-C(=O)-ORa, -CH2-phenyl, or 5-6-membered hetaryl, wherein the phenyl or hetaryl ring is unsubstituted or substituted with one or more RAr; wherein at least one of R2and R3is phenyl or 5- or 6-membered hetaryl unsubstituted or substituted with one or more RAr; wherein each RAris independently selected from halogen, N3, OH, CN, NO2, -SON, -SF5, Ci-Ce-alkyl, C1- Ce-alkoxy, C2-Ce-alkenyl, tri-Ci-Ce-alkylsilyl, C2-Ce-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C1- C6-alkoxy-Ci-C4-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(=O)-ORa, NRbRc, Ci-C6-alkylene-NRbRc, O-Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, NH-Ci-C6-alkylene-NRbRc, C(=O)-NRbRc, C(=O)-Rd, SO2NRbRc, or S(=O)mRe, phenyl, phenoxy, phenylcarbonyl, phenylthio or -CH2-phenyl, wherein phenyl rings are unsubstituted or substituted with one or more Rf, or two RArcombine to form together with the carbon atoms to which they are attached a 5- to 6-membered carbo- or heterocyclic ring unsubstituted or substituted with one or more Rf; m is 0, 1 , or 2;

[0020] R1is a moiety of formula X-Y-Z-T-R4; wherein

[0021] X is a single bond;

[0022] -(C(Rxa)2)P-, wherein p is an integer of 1 to 3, preferably 1 or 2;

[0023] -(C(Rxa)2)o-NRxc-, wherein 0 is an integer of 1 or 2 and N is bound to Y; or -NRXC-;

[0024] Y is -CRya=N-, wherein the N is bound to Z;

[0025] -NRyc-C(=O)-, wherein C(=O) is bound to Z; or -NRyc-C(=S)-, wherein C(=S) is bound to Z;

[0026] Z is -NRZC-C(=O)-, wherein C(=O) is bound to T;

[0027] -NRZC-C(=S)-, wherein C(=S) is bound to T;

[0028] -N=C(S-Rza)-, wherein T is bound to the carbon atom; or -NRzc-C(S-Rza)=, wherein T is bound to the carbon atom;

[0029] T is O, N or N-RT; 3

[0030] R4is aryl, aryl-Ci-C4-alkyl, hetaryl, or hetaryl-Ci-C4-alkyl, wherein the aryl or hetaryl rings are unsubstituted or substituted with one or more R9and wherein the hetaryl is a 5- or 6- membered monocyclic hetaryl or a 8-, 9- or 10-membered bicyclic hetaryl; and wherein

[0031] Rxa, Ryaare, identical or different, H, halogen, Ci-Ce-alkyl, Ci-Ce-alkoxy, C2-Ce-alkenyl, C2-C6- alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-alkyl-C3-C6-cycloalkyl, C1-C4- alkyl-Cs-Ce-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;

[0032] Rxc, Ryc, Rzcare, identical or different, H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, C1-C4- alkyl-Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, Ci-C4-alkyl-C3-C6-cycloalkyl, Ci-C4-alkyl-C3-Ce- cycloalkoxy, or -NRbRc, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;

[0033] RTis H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-C4-alkyl-Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;

[0034] Rzais H, Ci-Ce-alkyl, Ci-Ce-alkoxy, C2-Ce-alkenyl, tri-Ci-Ce-alkylsilyl, C2-Ce-alkynyl, C1-C4- alkyl-Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, Ci-C4-alkyl-C3-C6-cycloalkoxy, Ci-C4-alkyl-C3-Ce- cycloalkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, C(=O)-NRbRc, C(=O)-Rd, phenyl, phenylcarbonyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;

[0035] Rzatogether with RTor Rzcif present, may form a linear Ci-Ce-alkylene or a linear C2-C6- alkenylene group, where in the linear Ci-Ce-alkylene and the linear C2-Ce-alkenylene a CH2 moiety is optionally replaced by a carbonyl and / or wherein 1 or 2 CH2 moieties are optionally replaced by O or S and / or wherein the linear Ci-Ce-alkylene and the linear C2- Cs-alkenylene are unsubstituted or substituted with one or more Rh;

[0036] Ra, Rband Rcare, identical or different, H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-alkoxy- Ci-C4-alkyl, Cs-Ce-cycloalkyl, C3-Ce-cycloalkyl-Ci-C4-alkyl, C3-Ce-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

[0037] Ci-Ce-alkylene-CN, phenyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with one or more Rf;

[0038] Rdis H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-alkoxy-Ci-C4-alkyl, Cs-Ce-cycloalkyl, C3-Ce-cycloalkyl-Ci-C4-alkyl, C3-Ce-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, phenyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with one or more Rf; 4

[0039] Reis Ci-Ce-alkyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, wherein the alkyl, cycloalkyl moieties are unsubstituted or substituted with halogen, phenyl and -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with one or more Rf;

[0040] Rfis halogen, N3, OH, CN, NO2, -SON, -SF5, Ci-Ce-alkyl, Ci-Ce-alkoxy, C2-C6-alkenyl, tri-Ci- Ce-alkylsilyl, C2-C6-alkynyl, Ci-Ce-alkoxy-Ci-C4-alkyl, Ci-C6-alkoxy-Ci-C4-alkoxy, C3-C6- cycloalkyl, Cs-Ce-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxyx-Ci-C4- alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;

[0041] R9is halogen, N3, OH, CN, NO2, -SCN, -SF5, Ci-Ce-alkyl, Ci-Ce-alkoxy, C2-Ce-alkenyl, tri-Ci- Ce-alkylsilyl, C2-Ce-alkynyl, Ci-Ce-alkoxy-Ci-C4-alkyl, Ci-Ce-alkoxy-Ci-C4-alkoxy, C3-C6- cycloalkyl, Cs-Ce-cycloalkoxy, C3-Ce-cycloalkyl-Ci-C4-alkyl, C3-Ce-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

[0042] C(=O)-ORa, NRbRc, Ci-C6-alkylene-NRbRc, O-Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, NH-Ci-C6-alkylene-NRbRc, C(=O)-NRbRc, C(=O)-Rd, SO2NRbRc, or S(=O)mRe;

[0043] Rhis halogen, OH, Ci-Ce-alkyl, Cs-Ce-cycloalkyl, or CN; and the N-oxides, stereoisomers, tautomers, and agriculturally or veterinarily acceptable salts thereof.

[0044] In various embodiments, CRB1and / or CRB2are CH.

[0045] In various embodiments, R2is phenyl substituted with one or more RArand R3is H or methyl, preferably methyl. In various other embodiments, R3is phenyl substituted with one or more RArand R2is H.

[0046] In various embodiments of this aspect, R3is selected from the formulae Ar-1 to Ar-24 and one of R2is

[0047] H or R2or is selected from the formulae Ar-1 to Ar-24 and R3is H or methyl, preferably methyl: 5

[0048] In various embodiments of the compounds of formula (I),

[0049] (1) X is a single bond, Y is -CRya=N-, wherein the N is bound to Z, Z is -N=C(S-Rza)-, wherein T is bound to the carbon atom, and T is N-RT, wherein Rzatogether with RTforms a linear Ci-Ce-alkylene group, preferably C2 alkylene group, where in the linear Ci-Ce-alkylene a CH2 moiety is replaced by a carbonyl and wherein the linear Ci-Ce-alkylene is unsubstituted or substituted with Rh, and Ryais preferably H; or

[0050] (2) X is a single bond, Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is -N=C(S-Rza)-, wherein T is bound to the carbon atom, and T is N-RT, wherein Rzatogether with RTforms a linear Ci-Ce-alkylene group, preferably C2 alkylene group, where in the linear Ci-Ce- alkylene a CH2 moiety is replaced by a carbonyl and wherein the linear Ci-Ce-alkylene is unsubstituted or substituted with Rh, and Rycis preferably H; or

[0051] (3) X is -(C(Rxa)2)P-, wherein p is 2, Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is - N=C(S-Rza)-, wherein T is bound to the carbon atom, and T is N-RT, wherein Rzatogether with RTforms a linear Ci-Ce-alkylene group, preferably C2 alkylene group, where in the linear Ci-Ce-alkylene a CH2 moiety is replaced by a carbonyl and wherein the linear C1-C6- alkylene is unsubstituted or substituted with Rh, and all Rxaand Rycare preferably; or

[0052] (4) X is -(C(Rxa)2)o-NRxc-, wherein 0 is 1 and N is bound to Y, Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is -N=C(S-Rza)-, wherein T is bound to the carbon atom, and T is N-RT, wherein Rzatogether with RTforms a linear Ci-Ce-alkylene group, preferably C2 alkylene group, where in the linear Ci-Ce-alkylene a CH2 moiety is replaced by a carbonyl and wherein the linear Ci-Ce-alkylene is unsubstituted or substituted with Rh, and one Rxa, Rxcand Rycare preferably H and the other Rxais preferably methyl; or

[0053] (5) X is -(C(Rxa)2)o-NRxc-, wherein 0 is 1 and N is bound to Y, Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is -NRZC-C(=S)-, wherein C(=S) is bound to T, and T is N-RT, wherein one Rxa, Rxc, Ryc, Rzcand RTare preferably H and the other Rxais preferably methyl; 6

[0054] (6) X is -(C(Rxa)2)P-, wherein p is 1 , Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is - NRZC-C(=S)-, wherein C(=S) is bound to T, and T is N-RT, wherein one Rxa, Rzcand RTare preferably H, the other Rxais preferably methyl, and Rycis preferably -NH2;

[0055] (7) X is X is -(C(Rxa)2)o-NRxc-, wherein 0 is 1 and N is bound to Y, Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is -NRZC-C(=S)-, wherein C(=S) is bound to T, and T is N-RT, wherein one Rxa, Ryc, Rzcand RTare preferably H and the other Rxaand Rxcare preferably methyl; or

[0056] (8) X is -(C(Rxa)2)o-NRxc-, wherein 0 is 1 and N is bound to Y, Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is -N=C(S-Rza)-, wherein T is bound to the carbon atom, and T is N-RT, wherein Rzatogether with RTforms a linear Ci-Ce-alkylene group, preferably C2 alkylene group, where in the linear Ci-Ce-alkylene a CH2 moiety is replaced by a carbonyl and wherein the linear Ci-Ce-alkylene is unsubstituted or substituted with Rh, and one Rxaand Rycare preferably H and the other Rxaand Rxcare preferably methyl.

[0057] In various embodiments, R4is monocyclic or bicyclic aryl substituted with one or more R9, preferably phenyl, naphthyl, or pyridinyl optionally substituted with one or more R9.

[0058] In various embodiments, R4is selected from the following groups:

[0059] In various embodiments, R1is selected from the following groups: wherein # indicates the point of attachment. In various embodiments, R4 is preferably R4-29 or R4-31 .

[0060] In various embodiments, the compound of formula (I) is selected from any one of the following: 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 and the N-oxides, stereoisomers, tautomers, and agriculturally or veterinarily acceptable salts thereof.

[0061] In another aspect, the invention is directed to a composition, comprising at least one compound of formula (I) as disclosed herein and any one of a further active substance, an excipient or solvent. The compositions may be agricultural or veterinary compositions.

[0062] In still another aspect, the present invention is directed 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 or at least one composition according to the invention.

[0063] In a still further aspect, the invention relates to a method for protecting growing crops, plants, plant propagation material, growing plants or an animal from attack or infestation by invertebrate pests, which method may comprise contacting a plant, or soil or water wherein the plant is growing, or an animal with a pesticidally effective amount of at least one compound or at least one composition according to the invention or applying such.

[0064] In still another aspect, the invention relates to a seed comprising a compound or a composition according to the invention, preferably in an amount of from 0.1 g to 10 kg per 100 kg of seed.

[0065] In still another aspect, the invention relates to the use of a compound or of the compositions according to the invention, for protecting growing plants from attack or infestation by invertebrate pests.

[0066] In all embodiments and aspects described above, the compounds of formula (I) and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof may be used.

[0067] Detailed description

[0068] Unless otherwise indicated, all terms used therein have their common and scientifically accepted meaning.

[0069] Unless explicitly indicated otherwise, the term “compound(s) according to the invention” or “compound(s) of the invention” or “compound(s) of formula (I)”, refers to the compounds of formula I.

[0070] The term “compound(s) according to the invention”, or “compounds of formula I” comprises the compound(s) as defined herein as well as a stereoisomer, salt, tautomer or N-oxide thereof. The term “compound(s) of the present invention” is to be understood as equivalent to the term “compound(s) according to the invention”, therefore also comprising a stereoisomer, salt, tautomer or N-oxide thereof.

[0071] The term "composition(s) according to the invention" or "composition^) of the present invention" encompasses composition(s) comprising at least one compound of formula I according to the invention 24 as defined above. The compositions of the invention are preferably agricultural or veterinary compositions.

[0072] Depending on the substitution pattern, the compounds according to the invention may have one or more centers of chirality, in which case they can be present as mixtures of enantiomers or diastereomers. The invention provides both the single pure enantiomers or pure diastereomers of the compounds according to the invention, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compounds according to the invention or their mixtures. Suitable compounds according to the invention also include all possible geometrical stereoisomers (cis / trans isomers) and mixtures thereof. Cis / trans isomers may be present with respect to an alkene, carbon-nitrogen doublebond 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 present invention relates to every possible stereoisomer of the compounds of formula I, i.e. to single enantiomers or diastereomers, as well as to mixtures thereof.

[0073] The compounds according to the invention may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities. The present invention relates to amorphous and crystalline compounds according to the invention, mixtures of different crystalline states of the respective compounds according to the invention, as well as amorphous or crystalline salts thereof.

[0074] The term "tautomers" encompasses isomers, which are derived from the compounds of formula I by the shift of an H-atom involving at least one H-atom located at a nitrogen, oxygen or sulphur atom. Examples of tautomeric forms are keto-enol forms, imine-enamine forms, urea-isourea forms, thiourea-isothiourea forms, (thio)amide-(thio)imidate forms etc.

[0075] The term "stereoisomers" 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).

[0076] Depending on the substitution pattern, the compounds of the formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. The invention provides both the pure enantiomers or diastereomers and their mixtures and the use according to the invention of the pure enantiomers or diastereomers of the compound I or its mixtures. Suitable compounds of the formula I also include all possible geometrical stereoisomers (cis / trans isomers) and mixtures thereof.

[0077] The term N-oxides relates to a form of compounds I in which at least one nitrogen atom is present in oxidized form (as NO). To be more precise, it relates to any compound of the present invention which 25 has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety. N-oxides of compounds I can in particular be prepared by oxidizing e.g. the ring nitrogen atom of an N-heterocycle or an iminonitrogen with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides. The person skilled in the art knows if and in which positions compounds of the present invention may form N-oxides.

[0078] Salts of the compounds of the formula I are preferably agriculturally and veterinarily acceptable salts. 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.

[0079] Suitable agriculturally or veterinarily acceptable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, which are known and accepted in the art for the formation of salts for agricultural or veterinary use respectively, and do not have any adverse effect on the action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH4+) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4- alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or -CH2-phenyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyl-triethylammonium. Suitable anions include, but are not limited to, phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium. Suitable acid addition salts, e.g. formed by compounds of formula I containing a basic nitrogen atom, e.g. an amino group, include salts with inorganic acids, for example hydrochlorides, sulphates, phosphates, and nitrates and salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.

[0080] 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 Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound of formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

[0081] The term "invertebrate pest" as used herein encompasses animal populations, such as insects, arachnids and nematodes, which may attack plants, thereby causing substantial damage to the plants attacked, as well as ectoparasites which may infest animals, in particular warm blooded animals such 26 as e.g. mammals or birds, or other higher animals such as reptiles, amphibians or fish, thereby causing substantial damage to the animals infested.

[0082] The term "plant propagation material" is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used forthe multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. The plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting. Said young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.

[0083] The term "plants" comprises any types of plants including "modified plants" and in particular "cultivated plants".

[0084] The term "modified plants" refers to any wild type species or related species or related genera of a cultivated plant.

[0085] The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http: / / www.bio.org / speeches / pubs / er / agri_products.asp). Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.

[0086] Plants that have been modified by breeding, mutagenesis or genetic engineering, e. g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxylphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibittors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i.e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These 27 herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g. imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g. tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate-tolerant, Bayer CropScience, Germany).

[0087] Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as 6-endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insectspecific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA- reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02 / 015701). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93 / 007278, WO 95 / 34656, EP-A 427 529, EP-A 451 878, WO 03 / 18810 und WO 03 / 52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the CrylAb toxin), YieldGard® Plus (corn cultivars producing Cry1 Ab and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]); 28

[0088] NuCOTN® 33B (cotton cultivars producing the Cry1 Ac toxin), Bollgard® I (cotton cultivars producing the CrylAc toxin), Bollgard® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e. g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03 / 018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).

[0089] Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called “pathogenesis-related proteins” (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.

[0090] Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.

[0091] Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape, DOW Agro Sciences, Canada).

[0092] Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato, BASF SE, Germany).

[0093] The organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual members. The prefix Cn-Cmindicates in each case the possible number of carbon atoms in the group. 29

[0094] The term halogen denotes in each case F, Br, Cl or I, in particular F, Cl or Br.

[0095] The term "alkyl" as used herein and in the alkyl moieties of alkoxy, alkylthio, and the like refers to saturated straight-chain or branched hydrocarbon radicals having 1 to 2 ("Ci-C2-alkyl"), 1 to 3 ("C1-C3- alkyl"),1 to 4 ("Ci-C4-alkyl") or 1 to 6 ("Ci-C6-alkyl") carbon atoms. Ci-C2-Alkyl is CH3or C2H5. C1-C3- Alkyl is additionally propyl and isopropyl. Ci-C4-Alkyl is additionally butyl, 1 -methylpropyl (sec-butyl), 2- methylpropyl (isobutyl) or 1 ,1 -dimethylethyl (tert-butyl). Ci-Ce-Alkyl is additionally also, for example, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, 1 ,1- dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dime- thylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1- ethyl-1 -methylpropyl, or 1-ethyl-2-methylpropyl.

[0096] The term "haloalkyl" as used herein, which is also expressed as "alkyl which is partially or fully halogenated", refers to straight-chain or branched alkyl groups having 1 to 2 ("Ci-C2-haloalkyl"), 1 to 3 ("Ci-Cs-haloalkyl"), 1 to 4 ("Ci-C4-haloalkyl") or 1 to 6 ("Ci-Ce-haloalkyl") carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: in particular Ci-C2-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 or pentafluoroethyl. Ci-Cs-haloalkyl is additionally, for example, 1 -fluoropropyl, 2- fluoropropyl, 3-fluoropropyl, 1 ,1 -difluoropropyl, 2,2-difluoropropyl, 1 ,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1 , 1 , 1 -trifluoroprop-2-yl, 3-chloropropyl and the like. Examples for Ci-C4-haloalkyl are, apart those mentioned for Ci-Cs-haloalkyl, 4-chlorobutyl and the like.

[0097] The term "alkylene" (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety. Alkylene has preferably 1 to 6 carbon atoms (C1-C6- alkylene), 2 to 6 carbon atoms (C2-Ce-alkylene), in particular 1 to 4 carbon atoms (Ci-C4-alkylene) or 2 to 4 carbon atoms (C2-C4-alkylene). Examples of alkylene are methylene (CH2), 1 , 1 -ethandiyl, 1 ,2- ethandiyl, 1 ,3-propandiyl, 1 ,2-propandiyl, 2,2-propandiyl, 1 ,4-butandiyl, 1 ,2-butandiyl, 1 ,3-butandiyl, 2,3- butandiyl, 2,2-butandiyl, 1 ,5-pentandiyl, 2,2-dimethylpropan-1 ,3-diyl, 1 ,3-dimethyl-1 ,3-propandiyl, 1 ,6- hexandiyl etc.

[0098] The term "alkenyl" as used herein refers to monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 ("C2-C3-alkenyl"), 2 to 4 ("C2-C4-alkenyl") or 2 to 6 ("C2-C6-alkenyl) carbon atoms and a double bond in any position, for example C2-C3-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl or 1 -methylethenyl; C2-C4-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl, 1 -methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 -propenyl, 2-methyl-1 -propenyl, 1-methyl-2-propenyl or 2-methyl-2- 30 propenyl; C2-Ce-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl, 1 -methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 -propenyl, 2-methyl-1 -propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1- pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1- butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3- butenyl, 3-methyl-3-butenyl, 1 ,1-dimethyl-2-propenyl, 1 ,2-dimethyl-1 -propenyl, 1 ,2-dimethyl-2-propenyl, 1-ethyl-1 -propenyl, 1-ethyl-2-propenyl, 1 -hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1- methyl-1 -pentenyl, 2-methyl-1 -pentenyl, 3-methyl-1 -pentenyl, 4-methyl-1 -pentenyl, 1-methyl-2- pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2- methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4- pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1 ,1-dimethyl-2-butenyl, 1 ,1-dimethyl-3-butenyl,

[0099] 1 .2-dimethyl-1-butenyl, 1 ,2-dimethyl-2-butenyl, 1 ,2-dimethyl-3-butenyl, 1 ,3-dimethyl-1-butenyl,

[0100] 1 .3-dimethyl-2-butenyl, 1 ,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3- dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,

[0101] 1 -ethyl-1 -butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3- butenyl, 1 ,1 ,2-trimethyl-2-propenyl, 1 -ethyl-1 -methyl-2-propenyl, 1-ethyl-2-methyl-1 -propenyl, 1-ethyl-2- methyl-2-propenyl and the like.

[0102] The term "alkynyl" as used herein refers to straight-chain or branched hydrocarbon groups having 2 to 3 ("C2-C3-alkynyl"), 2 to 4 ("C2-C4-alkynyl") or 2 to 6 ("C2-C6-alkynyl") carbon atoms and one or two triple bonds in any position, for example C2-C3-alkynyl, such as ethynyl, 1-propynyl or 2-propynyl; C2-C4- alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like, C2-Ce-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1- methyl-2-propynyl, 1 -pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3- butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1 ,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl,

[0103] 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4- pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1 -pentynyl, 3-methyl-4-pentynyl, 4- methyl-1 -pentynyl, 4-methyl-2-pentynyl, 1 ,1-dimethyl-2-butynyl, 1 ,1-dimethyl-3-butynyl, 1 ,2-dimethyl-3- butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1 -ethyl-2-butynyl, 1 -ethyl-3-butynyl, 2-ethyl-3- butynyl, 1 -ethyl-1 -methyl-2-propynyl and the like.

[0104] The term "cycloalkyl" as used herein refers to mono- or bi- or polycyclic saturated hydrocarbon radicals having in particular 3 to 6 ("Cs-Ce-cycloalkyl") or 3 to 5 ("Cs-Cs-cycloalkyl") or 3 to 4 ("C3-C4-cycloalkyl") carbon atoms. Examples of monocyclic radicals having 3 to 4 carbon atoms comprise cyclopropyl and cyclobutyl. Examples of monocyclic radicals having 3 to 5 carbon atoms comprise cyclopropyl, cyclobutyl and cyclopentyl. Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of monocyclic radicals having 3 to 8 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.2.1]heptyl, bicyclo- [3.1 .1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl. Preferably, the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical. 31

[0105] The term "cycloalkoxy" as used herein refers to a cycloalkyl radical, in particular a monocyclic cycloalkyl radical, as defined above having in particular 3 to 6 ("Cs-Ce-cycloalkoxy") or 3 to 5 ("Cs-Cs-cycloalkoxy") or 3 to 4 ("C3-C4-cycloalksoxy") carbon atoms, which is bound via an oxygen atom to the remainder of the molecule.

[0106] The term "cycloalkyl-Ci-C4-alkyl" refers to a Cs-Cs-cycloalkyl ("C3-C8-cycloalkyl-Ci-C4-alkyl"), preferably a Cs-Ce-cycloalkyl ("C3-C6-cycloalkyl-Ci-C4-alkyl"), more preferably a C3-C4-cycloalkyl ("C3-C4- cycloalkyl-Ci-C4-alkyl") as defined above (preferably a monocyclic cycloalkyl group) which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above. Examples for C3-C4-cycloalkyl- Ci-C4-alkyl are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl and cyclobutylpropyl, Examples for C3-C6-cycloalkyl-Ci-C4-alkyl, apart those mentioned for C3-C4- cycloalkyl-Ci-C4-alkyl, are cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl.

[0107] The term "Ci-C2-alkoxy" refers to a Ci-C2-alkyl group, as defined above, attached via an oxygen atom. The term "Ci-Cs-alkoxy" is a Ci-Cs-alkyl group, as defined above, attached via an oxygen atom. The term "Ci-C4-alkoxy" is a Ci-C4-alkyl group, as defined above, attached via an oxygen atom. The term "Ci-Ce-alkoxy" is a Ci-Ce-alkyl group, as defined above, attached via an oxygen atom. The term "C1- Cio-alkoxy" is a Ci-Cio-alkyl group, as defined above, attached via an oxygen atom. Ci-C2-Alkoxy is OCH3 or OC2H5. Ci-Cs-Alkoxy is additionally, for example, n-propoxy and 1 -methylethoxy (isopropoxy). Ci-C4-Alkoxy is additionally, for example, butoxy, 1 -methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1 -dimethylethoxy (tert-butoxy). Ci-Ce-Alkoxy is additionally, for example, pentoxy, 1- methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4- methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3- dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2- trimethylpropoxy, 1 -ethyl-1 -methylpropoxy or 1-ethyl-2-methylpropoxy. Ci-Cs-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof. Ci-Cio-Alkoxy is additionally, for example, nonyloxy, decyloxy and positional isomers thereof.

[0108] The term "Ci-C2-haloalkoxy" is a Ci-C2-haloalkyl group, as defined above, attached via an oxygen atom.

[0109] The term "Ci-Cs-haloalkoxy" is a Ci-Cs-haloalkyl group, as defined above, attached via an oxygen atom.

[0110] The term "Ci-C4-haloalkoxy" is a Ci-C4-haloalkyl group, as defined above, attached via an oxygen atom.

[0111] The term "Ci-Ce-haloalkoxy" is a Ci-Ce-haloalkyl group, as defined above, attached via an oxygen atom.

[0112] Ci-C2-Haloalkoxy is, for example, OCH2F, OCHF2, OCF3, OCH2CI, OCHCh, OCCh, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2- chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy orOC2F5. Ci-Cs-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 32

[0113] 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3- trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2CI)-2- chloroethoxy or 1-(CH2Br)-2-bromoethoxy. Ci-C4-Haloalkoxy is additionally, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. Ci-Ce-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6- fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.

[0114] The term "Ci-C6-alkoxy-Ci-C4-alkyl" as used herein, refers to a straight-chain or branched alkyl having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-Ce-alkoxy group, as defined above. Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n- butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, 1 -methoxyethyl, 1 -ethoxyethyl, 1- propoxyethyl, 1 -isopropoxyethyl, 1-n-butoxyethyl, 1-sec-butoxyethyl, 1 -isobutoxyethyl, 1-tert- butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec- butoxyethyl, 2-isobutoxyethyl, 2-tert-butoxyethyl, 1 -methoxypropyl, 1 -ethoxypropyl, 1 -propoxypropyl, 1- isopropoxypropyl, 1-n-butoxypropyl, 1-sec-butoxypropyl, 1 -isobutoxypropyl, 1-tert-butoxypropyl, 2- methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-isopropoxypropyl, 2-n-butoxypropyl, 2-sec- butoxypropyl, 2-isobutoxypropyl, 2-tert-butoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3- propoxypropyl, 3-isopropoxypropyl, 3-n-butoxypropyl, 3-sec-butoxypropyl, 3-isobutoxypropyl, 3-tert- butoxypropyl and the like. As described above, the alkyl or alkoxy moieties may be substituted, in particular halogenated. Exemplary groups include, without limitation, trifluoroethoxymethyl.

[0115] The term "alkoxyalkoxy" as used herein refers to an alkoxyalkyl radical, in particular a Ci-Ce-alkoxy-Ci- C4-alkyl radical, as defined above, which is bound via an oxygen atom to the remainder of the molecule. Examples thereof are OCH2-OCH3, OCH2-OC2H5, n-propoxymethoxy, OCH2-OCH(CH3)2, n-butoxymethoxy, (l-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, OCH2-OC(CH3)3, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy, 2-(1-methylethoxy)ethoxy, 2-(n-butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1 ,1-dimethyl- ethoxy)ethoxy, etc.

[0116] The substituent "oxo" replaces a CH2 by a C(=O) group.

[0117] The term "aryl" relates to phenyl and bi- or polycyclic carbocycles having at least one fused phenylene ring, which is bound to the remainder of the molecule. Examples of bi- or polycyclic carbocycles having at least one phenylene ring include naphthyl, tetrahydronaphthyl, indanyl, indenyl, anthracenyl, fluorenyl etc.

[0118] The term "aryl-Ci-C4-alkyl" relates to Ci-C4-alkyl, as defined above, wherein one hydrogen atom has been replaced by an aryl radical, in particular a phenyl radical. Particular examples of aryl-Ci-C4-alkyl include -CFh-phenyl, 1 -phenethyl, 2-phenetyl, 1 -phenylpropyl, 2-phenylpropyl, 3-phenyl-1 -propyl and 2- phenyl-2-propyl. 33

[0119] The term "aryloxy-Ci-C4-alkyl" relates to Ci-C4-alkyl, as defined above, wherein one hydrogen atom has been replaced by an aryloxy radical, in particular a phenoxy radical. Particular examples of aryloxy-Ci- C4-alkyl include phenoxymethyl, 1 -phenoxyethyl, 2-phenoxyetyl, 1 -phenoxypropyl, 2-phenoxypropyl, 3- phenoxy-1 -propyl and 2-phenoxy-2-propyl.

[0120] The term "aryl-Ci-C4-carbonyl" relates to aryl as defined above, in particular a phenyl radical, which is bound by a carbonyl to the remainder of the molecule. Particular examples of arylcarbonyl include benzoyl, 1 -naphthoyl and 2-naphthoyl.

[0121] The term “hetaryl” relates to aromatic heterocycles having either 5 or 6 ring atoms (5- or 6-membered hetaryl) and being monocyclic or 8, 9 or 10 ring atoms and bing bicyclic. Hetaryl will generally have at least one ring atom selected from O, S and N, which in case of N may be an imino-nitrogen or an aminonitrogen, which carries hydrogen or a radical different from hydrogen. Hetaryl may have 1 , 2, 3 or 4 further nitrogen atoms as ring members, which are imino nitrogens. Examples of 5- or 6-membered hetaryl include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1 -pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3- pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1 -imidazolyl, 2-imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-1-yl, 1 ,3,4-triazol-2-yl, 1 ,3,4-oxadiazolyl-2-yl, 1 ,3,4- thiadiazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl and 1 ,3,5-triazin-2-yl. Examples of 8-, 9- or 10-membered hetaryl include, for example, quinolinyl, isoquinolinyl, cinnolinyl, indolyl, indolizynyl, isoindolyl, indazolyl, benzofuryl, benzothienyl, benzo[b]thiazolyl, benzoxazolyl, benzthiazolyl, benzimidazolyl, imidazo[1 ,2- a]pyridine-2-yl, thieno[3,2-b]pyridine-5-yl, imidazo-[2,1-b]-thiazol-6-yl and 1 ,2,4-triazolo[1 ,5-a]pyridine- 2-yl.

[0122] Examples of N-bound 5-, 6-, 7 or 8-membered saturated heterocycles include: pyrrolidin-1 -yl, pyrazolidin-1 -yl, imidazolidin-1 -yl, oxazolidin-3-yl, isoxazolidin-2-yl, thiazolidin-3-yl, isothiazolidin-2-yl, piperidin-1-yl, piperazin-1 -yl, morpholin-4-yl, thiomorpholin-4-yl, 1-oxothiomorpholin-4-yl, 1 ,1- dioxothiomorpholin-4-yl, azepan-1-yl and the like.

[0123] The term "hetaryl-Ci-C4-alkyl" relates to Ci-C4-alkyl, as defined above, wherein one hydrogen atom has been replaced by a hetaryl radical, in particular a pyridyl radical. Particular examples of hetaryl-Ci-C4- alkyl include 2-pyridylmethyl, 3-pyridylmethyl, 4-pyridylmethyl, 1-(2-pyridyl)ethyl, 2-(2-pyridyl)ethyl, 1-(3- pyridyl)ethyl, 2-(3-pyridyl)ethyl, 1-(4-pyridyl)ethyl, 2-(4-pyridyl)ethyl etc..

[0124] The term "hetaryloxy-Ci-C4-alkyl" relates to Ci-C4-alkyl, as defined above, wherein one hydrogen atom has been replaced by an hetaryloxy radical, in particular a pyridyloxy radical. Particular examples of hetaryloxy-Ci-C4-alkyl include 2-pyridyloxymethyl, 3-pyridyloxymethyl, 4-pyridyloxymethyl, 1-(2- pyridyloxy)ethyl, 2-(2-pyridyloxy)ethyl, 1-(3-pyridyloxy)ethyl, 2-(3-pyridyloxy)ethyl, 1-(4-pyridyloxy)ethyl, 2-(4-pyridyloxy)ethyl etc. The term "hetaryl-Ci-C4-carbonyl" relates to hetaryl as defined above, in particular a C-bound hetaryl radical, e.g. 2-, 3-or 4-pyridyl, 2- or 3-thienyl, 2- or 3-furyl, 1-, 2- or 3-pyrrolyl, 2- or 4-pyrimidinyl, pyridazinyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4-imidazolyl radical, which is bound by a carbonyl to the remainder of the molecule.

[0125] The term “substituted” if not specified otherwise refers to substituted with 1 , 2 or maximum possible number of substituents. If substituents as defined in compounds of formula I are more than one then they are independently from each other are same or different if not mentioned otherwise.

[0126] The compounds of the invention are compounds of formula (I) wherein

[0127] B1is CRB1;

[0128] B2is CRB2;

[0129] RB1and RB2independently of each other are H, halogen, N3, OH, CN, NO2, -SON, -SF5, Ci-Ce-alkyl, C1- Ce-alkoxy, C2-Ce-alkenyl, tri-Ci-Ce-alkylsilyl, C2-Ce-alkynyl, Ci-Ce-alkoxy-Ci-C4-alkyl, Ci-Ce- alkoxy-Ci-C4-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, C1-C4- alkyl-Cs-Ce-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

[0130] C(=O)-ORa, NRbRc, Ci-C6-alkylene-NRbRc, O-Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, NH-C1- C6-alkylene-NRbRc, C(=O)-NRbRc, C(=O)-Rd, SO2NRbRc, or S(=O)mRe, phenyl, phenoxy, phenylcarbonyl, phenylthio, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with one or more Rf;

[0131] R2and R3are H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(=O)-ORa, Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, C(=O)-NRbRc, C(=O)-Rd, SO2NRbRc, S(=O)mRe, phenyl, -CH2-C(=O)-ORa, -CH2-phenyl, or 5-6-membered hetaryl, wherein the phenyl or hetaryl ring is unsubstituted or substituted with one or more RAr; wherein at least one of R2and R3is phenyl or 5- or 6-membered hetaryl unsubstituted or substituted with one or more RAr; wherein each RAris independently selected from halogen, N3, OH, CN, NO2, -SCN, -SF5, Ci-Ce-alkyl, C1- Ce-alkoxy, C2-Ce-alkenyl, tri-Ci-Ce-alkylsilyl, C2-Ce-alkynyl, Ci-Ce-alkoxy-Ci-C4-alkyl, C1- Ce-alkoxy-Ci-C4-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-cycloalkoxy, C3-Ce-cycloalkyl-Ci-C4-alkyl, C3-Ce-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(=O)-ORa, NRbRc, Ci-C6-alkylene-NRbRc, O-Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, 35

[0132] NH-Ci-C6-alkylene-NRbRc, C(=O)-NRbRc, C(=O)-Rd, SO2NRbRc, or S(=O)mRe, phenyl, phenoxy, phenylcarbonyl, phenylthio or -CH2-phenyl, wherein phenyl rings are unsubstituted or substituted with one or more Rf, or two RArcombine to form together with the carbon atoms to which they are attached a 5- to 6-membered carbo- or heterocyclic ring unsubstituted or substituted with one or more Rf; m is 0, 1 , or 2;

[0133] R1is a moiety of formula X-Y-Z-T-R4; wherein

[0134] X is a single bond;

[0135] -(C(Rxa)2)P-, wherein p is an integer of 1 to 3, preferably 1 or 2;

[0136] -(C(Rxa)2)o-NRxc-, wherein o is an integer of 1 or 2 and N is bound to Y; or -NRXC-;

[0137] Y is -CRya=N-, wherein the N is bound to Z;

[0138] -NRyc-C(=O)-, wherein C(=O) is bound to Z; or -NRyc-C(=S)-, wherein C(=S) is bound to Z;

[0139] Z is -NRZC-C(=O)-, wherein C(=O) is bound to T;

[0140] -NRZC-C(=S)-, wherein C(=S) is bound to T;

[0141] -N=C(S-Rza)-, wherein T is bound to the carbon atom; or -NRzc-C(S-Rza)=, wherein T is bound to the carbon atom;

[0142] T is O, N or N-RT;

[0143] R4is aryl, aryl-Ci-C4-alkyl, hetaryl, or hetaryl-Ci-C4-alkyl, wherein the aryl or hetaryl rings are unsubstituted or substituted with one or more R9and wherein the hetaryl is a 5- or 6- membered monocyclic hetaryl or a 8-, 9- or 10-membered bicyclic hetaryl; and wherein

[0144] Rxa, Ryaare, identical or different, H, halogen, Ci-Ce-alkyl, Ci-Ce-alkoxy, C2-Ce-alkenyl, C2-C6- alkynyl, Ci-Ce-alkoxy-Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-alkyl-C3-C6-cycloalkyl, C1-C4- alkyl-Cs-Ce-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;

[0145] Rxc, Ryc, Rzcare, identical or different, H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, C1-C4- alkyl-Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, Ci-C4-alkyl-C3-C6-cycloalkyl, Ci-C4-alkyl-C3-Ce- cycloalkoxy, or -NRbRc, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;

[0146] RTis H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-C4-alkyl-Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;

[0147] Rzais H, Ci-Ce-alkyl, Ci-Ce-alkoxy, C2-Ce-alkenyl, tri-Ci-Ce-alkylsilyl, C2-Ce-alkynyl, C1-C4- alkyl-Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, Ci-C4-alkyl-C3-C6-cycloalkoxy, Ci-C4-alkyl-C3-Ce- cycloalkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, 36

[0148] Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, C(=O)-NRbRc, C(=O)-Rd, phenyl, phenylcarbonyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;

[0149] Rzatogether with RTor Rzcif present, may form a linear Ci-Ce-alkylene or a linear C2-C6- alkenylene group, where in the linear Ci-Ce-alkylene and the linear C2-C6-alkenylene a CH2 moiety is optionally replaced by a carbonyl and / or wherein 1 or 2 CH2 moieties are optionally replaced by O or S and / or wherein the linear Ci-Ce-alkylene and the linear C2- Cs-alkenylene are unsubstituted or substituted with one or more Rh;

[0150] Ra, Rband Rcare, identical or different, H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-alkoxy- Ci-C4-alkyl, Cs-Ce-cycloalkyl, C3-Ce-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

[0151] Ci-Ce-alkylene-CN, phenyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with one or more Rf;

[0152] Rdis H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-alkoxy-Ci-C4-alkyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, phenyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with one or more Rf;

[0153] Reis Ci-Ce-alkyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, wherein the alkyl, cycloalkyl moieties are unsubstituted or substituted with halogen, phenyl and -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with one or more Rf;

[0154] Rfis halogen, N3, OH, CN, NO2, -SON, -SF5, Ci-Ce-alkyl, Ci-Ce-alkoxy, C2-Ce-alkenyl, tri-Ci- Ce-alkylsilyl, C2-Ce-alkynyl, Ci-Ce-alkoxy-Ci-C4-alkyl, Ci-Ce-alkoxy-Ci-C4-alkoxy, C3-C6- cycloalkyl, Cs-Ce-cycloalkoxy, C3-Ce-cycloalkyl-Ci-C4-alkyl, C3-Ce-cycloalkoxyx-Ci-C4- alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;

[0155] R9is halogen, N3, OH, CN, NO2, -SCN, -SF5, Ci-Ce-alkyl, Ci-Ce-alkoxy, 02-Ce-alkenyl, tri-Ci- Ce-alkylsilyl, 02-Ce-alkynyl, Ci-Ce-alkoxy-Ci-C4-alkyl, Ci-Ce-alkoxy-Ci-C4-alkoxy, C3-C6- cycloalkyl, Cs-Ce-cycloalkoxy, C3-Ce-cycloalkyl-Ci-C4-alkyl, C3-Ce-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

[0156] C(=O)-ORa, NRbRc, Ci-C6-alkylene-NRbRc, O-Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, NH-Ci-C6-alkylene-NRbRc, C(=O)-NRbRc, C(=O)-Rd, SO2NRbRc, or S(=O)mRe;

[0157] Rhis halogen, OH, Ci-Ce-alkyl, Cs-Ce-cycloalkyl, or CN. 37

[0158] Also encompassed are the N-oxides, stereoisomers, tautomers, and agriculturally or veterinarily acceptable salts of the compounds of formula (I).

[0159] With respect to the variables, embodiments of the compounds of the formula I are the following:

[0160] In various embodiments, B1is CRB1and RB1is H, halogen, such as Cl or F, or Ci-Ce-alkyl, optionally substituted with halogen, preferably CH.

[0161] In various embodiments, B2is CRB2and RB2is H, halogen, such as Cl or F, or Ci-Ce-alkyl, optionally substituted with halogen, preferably CH.

[0162] In various embodiments, B1and B2are CRB1and CRB2and RB1and RB2are, independently, H, halogen, such as Cl or F, or Ci-Ce-alkyl, optionally substituted with halogen. Preferably both B1and B2are CH.

[0163] In various embodiments, R2or R3is H or Ci-Ce-alkyl, optionally substituted with halogen, preferably H or methyl, and the other is phenyl or 5- or 6-membered hetaryl unsubstituted or substituted with one or more RAr.

[0164] In various embodiments, R3is H or Ci-Ce-alkyl, optionally substituted with halogen, preferably H or methyl, and R2is phenyl or 5- or 6-membered hetaryl unsubstituted or substituted with one or more RAr. In various other embodiments, R2is H or Ci-Ce-alkyl, optionally substituted with halogen, preferably H, and R3is phenyl or 5- or 6-membered hetaryl unsubstituted or substituted with one or more RAr.

[0165] In various embodiments, R3is H or Ci-Ce-alkyl, optionally substituted with halogen, preferably H or methyl, more preferably methyl, and R2is phenyl unsubstituted or substituted with one or more RAr. In various other embodiments, R2is H or Ci-Ce-alkyl, optionally substituted with halogen, preferably H, and R3is phenyl unsubstituted or substituted with one or more RAr.

[0166] In various embodiments, R3is H or Ci-Ce-alkyl, optionally substituted with halogen, preferably H or methyl, more preferably methyl, and R2is phenyl substituted with one or more RAr, preferably substituted with 1 or 2 RAr. In various other embodiments, R2is H or Ci-Ce-alkyl, optionally substituted with halogen, preferably H, and R3is phenyl substituted with one or more RAr, preferably substituted with 1 or 2 RAr.

[0167] In various embodiments, R3is H or Ci-Ce-alkyl, optionally substituted with halogen, preferably H or methyl, more preferably methyl, and R2is 5- or 6-membered hetaryl unsubstituted or substituted with one or more RAr. In various other embodiments, R2is H or Ci-Ce-alkyl, optionally substituted with halogen, preferably H, and R3is 5- or 6-membered hetaryl unsubstituted or substituted with one or more RAr. 38

[0168] In various embodiments, R3is H or Ci-Ce-alkyl, optionally substituted with halogen, preferably H or methyl, more preferably methyl, and R2is 5- or 6-membered hetaryl substituted with one or more RAr, preferably substituted with 1 , 2 or 3 RAr. In various other embodiments, R2is H or Ci-Ce-alkyl, optionally substituted with halogen, preferably H, and R3is 5- or 6-membered hetaryl substituted with one or more RAr, preferably substituted with 1 , 2 or 3 RAr.

[0169] In various embodiments, R3is H or Ci-Ce-alkyl, optionally substituted with halogen, preferably H or methyl, more preferably methyl, and R2is 5- or 6-membered hetaryl, preferably selected from N- containing hetaryl, more preferably selected from pyridine, pyrimidine, pyridazine, pyrazine, triazole, and thiadiazol, even more preferably from pyridine, pyrimidine, pyridazine, pyrazine, 1 ,2,4-triazole, 1 ,3,4- triazole and 1 ,3,4-thiadiazol, substituted with one or more RAr, preferably substituted with 1 , 2 or 3 RAr. In various other embodiments, R2is H or Ci-Ce-alkyl, optionally substituted with halogen, preferably H, and R3is 5- or 6-membered hetaryl .preferably selected from N-containing hetaryl, more preferably selected from pyridine, pyrimidine, pyridazine, pyrazine, triazole, and thiadiazol, even more preferably from pyridine, pyrimidine, pyridazine, pyrazine, 1 ,2,4-triazole, 1 ,3,4-triazole and 1 ,3,4-thiadiazol, substituted with one or more RAr, preferably substituted with 1 , 2 or 3 RAr.

[0170] In various embodiments, RAris selected from halogen, preferably Cl and / or F, Ci-Ce-alkyl, Ci-Ce-alkoxy, or S(=O)mRe, wherein m is 0 and wherein the alkyl and alkoxy moieties are unsubstituted or substituted with halogen and wherein Reis Ci-Ce-alkyl unsubstituted or (preferably) substituted with halogen. In these embodiments, the Ci-Ce-alkyl and Ci-Ce-alkoxy moieties are preferably substituted with halogen, preferably Cl or F, more preferably F. Preferred RArsubstituents include, but are not limited to, trifluoromethyl, trifluoromethoxy, pentafluoroethoxy, trifluoromethylthio, fluoro, methyl, chloro, 2,2,2,- trifluoroethoxy, difluoromethoxy, difluoromethyl, 2,2-difluoroethoxy, and difluoromethylthio. These embodiments of RArare particularly preferred if R2or R3is substituted phenyl or substituted 5- or 6- membered hetaryl, as defined in the preferred embodiments above.

[0171] In various embodiments, if R2or R3is phenyl substituted with at least one RAr, said substituent RAris in the para position, in particular if only one RAris present. If two or more RArare present and R2or R3is phenyl, one is in the para position and the second one is preferably in the meta or ortho position, relative to the attachment to the core structure. The para-position substituent may, if it is the only substituent, preferably be trifluoromethoxy or chloro. If there are two substituents, the para substituent may be fluoro and the meta substituent chloro.

[0172] In various embodiments, two RArmay combine to form together with the carbon atoms to which they are attached a 5- to 6-membered carbo- or heterocyclic ring unsubstituted or substituted with one or more Rf. In various embodiments, the two RArwhich combine are bound to adjacent carbon atoms. In various embodiments, the ring formed is a heterocyclic ring, preferably with 1 or two oxygen ring atoms, in particular -O-C(Rf)2-O-, thus forming an 1 ,3-dioxolane ring. In various embodiments, Rfis halogen, such 39 as fluoro. Particularly preferred is a 2,2-difluoro-1 ,3-dioxolane ring. In various embodiments, R2and / or R3may thus be a 2,2-difluoro-1 ,3-benzodioxole and the respective other may be H.

[0173] In various embodiments, if R2or R3is pyridine, it is pyridine-3-yl, with the pyridine ring optionally substituted in the 6-position or the 2,4,5-positions. In various embodiments, if R2or R3is pyridazin, it is pyridazin-3-yl, with the pyridazine ring optionally further substituted in the 5- or 6-position. In various embodiments, if R2or R3is thiadiazol, it is 1 , 3 ,4-th iad iazol-2-y I , with the thiadiazole ring optionally further substituted in the 5-position.

[0174] In various embodiments, R2and / or R3may be selected from the following groups:

[0175] In such embodiments, only R2or R3may be selected from these groups and the other is H or Ci-Ce- alkyl, optionally substituted with halogen, preferably H or methyl. If R2is selected from these groups, R3is preferably methyl. If R3is selected from these groups, R2is preferably H.

[0176] Particularly preferred Ar is Ar-1 , Ar-2, Ar-20, Ar-23 and Ar-24. 40

[0177] In various embodiments, R2is Ar-1 and R3is methyl.

[0178] In various embodiments, R2is Ar-2 and R3is methyl.

[0179] In various embodiments, R2is Ar-20 and R3is methyl.

[0180] In various embodiments, R2is Ar-23 and R3is methyl.

[0181] In various embodiments, R2is Ar-24 and R3is methyl.

[0182] In various embodiments, R3is Ar-1 and R2is H.

[0183] In various embodiments, R3is Ar-2 and R2is H.

[0184] In various embodiments, R3is Ar-20 and R2is H.

[0185] In various embodiments, R3is Ar-23 and R2is H.

[0186] In various embodiments, R3is Ar-24 and R2is H.

[0187] R1is X-Y-Z-T-R4.

[0188] In various embodiments, X is a single bond, i.e. Y is directly linked to the pyrazine ring of formula (I). In such embodiments, R1may thus be -Y-Z-T-R4.

[0189] In various other embodiments, X is -(C(Rxa)2)P-, wherein p is an integer of 1 to 3, preferably 1 or 2. In various embodiments, p is 1 . In various other embodiments, p is 2. In various embodiments, Rxais H or methyl. If one Rxais methyl, the others are preferably H. In various embodiments, X is CH2-CH2 or - CH(CH3)-.

[0190] In various embodiments, X is -(C(Rxa)2)o-NRxc-, wherein 0 is an integer of 1 or 2 and N is bound to Y. In various embodiments, 0 is 1 . In various other embodiments, 0 is 2. In various embodiments, Rxais H or methyl. If one Rxais methyl, the others are preferably H. In various embodiments, Rxcis H, methyl or NRbRc, preferably H, methyl or NH2. In various embodiments, X is -CH(CH3)-NH- or X is -CH(CH3)- N(CH3)- or X is -CH2-NH- or X is -CH2-N(CH3)-.

[0191] In various embodiments, X is -NRXC-, wherein Rxcis preferably H.

[0192] In various embodiments, Y is -CRya=N-, wherein the N is bound to Z. 41

[0193] In various embodiments, Ryais H, halogen, Ci-Ce-alkyl, Ci-Ce-alkoxy, which are unsubstituted or substituted with halogen, phenyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf. In more preferred embodiment, Ryais H, halogen, Ci-Ce-alkyl, Ci-Ce-alkoxy, which are unsubstituted or substituted with halogen, or phenyl which is unsubstituted or substituted with Rf. In even more preferred embodiments, Ryais H, F, Cl , Br, CH3, C2H5, n-CsH?, isopropyl, CH2F, CHF2, CF3, CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2, CH2CF2CF3, OCH3, OC2H5, n-propyloxy, isopropyloxy, OCH2F, OCHF2, OCF3, OCH2CF3, OCF2CHF2, OC2F5, OCH2CH2CF3, OCH2CF2CHF2, OCH2CF2CF3, or phenyl which is unsubstituted or substituted with Rf. In the most preferred embodiment, Ryais H or CH3, in particular H.

[0194] In other various embodiments, Y is -NRyc-C(=S)-, wherein C(=S) is bound to Z. In such embodiments, Rycmay be H.

[0195] In still other various embodiments, Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z. In such embodiments, Rycmay be H or NRbRc, for example H or NH2.

[0196] In various embodiments, Rycis H, Ci-Ce-alkyl, Cs-Ce-cycloalkyl, which are unsubstituted or substituted with halogen, NRbRc, phenyl, or-CFh-phenyl, wherein the rings are unsubstituted or substituted with Rf. In preferred embodiment, Rycis H, Ci-Ce-alkyl, Ci-Ce-haloalkyl, NRbRc, or phenyl which is unsubstituted or substituted with Rf. In even more preferred embodiments, Rycis H, CH3, C2H5, n-CsH?, isopropyl, CH2F, CHF2, CF3, CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2, CH2CF2CF3, NH2, or phenyl which is unsubstituted or substituted with Rf. In most preferred embodiments, Rycis H, NH2 or CH3, in particular NH2 or H.

[0197] In various embodiments, Z is -NRZC-C(=O)-, wherein C(=O) is bound to T. In such embodiments, Rzcis preferably H.

[0198] In various embodiments, Z is -NRZC-C(=S)-, wherein C(=S) is bound to T. In such embodiments, Rzcis preferably H.

[0199] In various embodiments, Z is -N=C(S-Rza)-, wherein T is bound to the carbon atom, i.e. -N=C(S-Rza)- T. In such embodiments, Rzapreferably combines with RTto form a ring. For this, Rzaand RTmay combine to form a linear Ci-Ce-alkylene or a linear C2-Ce-alkenylene group, where in the linear C1-C6- alkylene and the linear C2-Ce-alkenylene a CH2 moiety is optionally replaced by a carbonyl and / or wherein 1 or 2 CH2 moieties are optionally replaced by O or S and / or wherein the linear Ci-Ce-alkylene and the linear C2-Ce-alkenylene are unsubstituted or substituted with one or more Rh. Preferably, the formed ring is a 5-membered ring, i.e. Rzaand RTtogether are a C2 alkylene or alkenylene group, preferably a C2 alkylene group, more preferably a C2 alkylene group in which a CH2 group is replaced by a carbonyl group. Most preferably, Rzaand RTtogether are -CH2-C(=O)-. 42

[0200] In various embodiments, Z is -NRzc-C(S-Rza)=, wherein T is bound to the carbon atom, i.e. -NRZC- C(S-Rza)=. In such embodiments, Rzamay combine with RTor Rzcto form a ring. For this, Rzaand RT(or Rzc) may combine to form a linear Ci-Ce-alkylene or a linear C2-C6-alkenylene group, where in the linear Ci-Ce-alkylene and the linear C2-C6-alkenylene a CH2 moiety is optionally replaced by a carbonyl and / or wherein 1 or 2 CH2 moieties are optionally replaced by O or S and / or wherein the linear Ci-Ce- alkylene and the linear C2-Ce-alkenylene are unsubstituted or substituted with one or more Rh. Preferably, the formed ring is a 5-membered ring, i.e. Rzaand RTtogether are a C2 alkylene or alkenylene group, preferably a C2 alkylene group, more preferably a C2 alkylene group in which a CH2 group is replaced by a carbonyl group. Most preferably, Rzaand RTtogether are -CH2-C(=O)-.

[0201] It is preferred that Z is -NRZC-C(=S)-, wherein C(=S) is bound to T and Rzcis preferably H or that Z is - N=C(S-Rza)-, wherein T is bound to the carbon atom, i.e. -N=C(S-Rza)-T. In such embodiments, Rzapreferably combines with RTto form a ring. For this, Rzaand RTmay combine to form a linear Ci-Ce- alkylene or a linear C2-Ce-alkenylene group, where in the linear Ci-Ce-alkylene and the linear C2-C6- alkenylene a CH2 moiety is optionally or preferably replaced by a carbonyl and / or wherein 1 or 2 CH2 moieties are optionally replaced by O or S and / or wherein the linear Ci-Ce-alkylene and the linear C2- Cs-alkenylene are unsubstituted or substituted with one or more Rh, preferably unsubstituted. Rzaand RTmay combine to form a linear Ci-Ce-alkylene group, where in the linear Ci-Ce-alkylene a CH2 moiety is preferably replaced by a carbonyl and / or wherein the linear Ci-Ce-alkylene and the linear C2-C6- alkenylene are unsubstituted or substituted with one or more Rh, preferably unsubstituted. Preferably, the formed ring is a 5-membered ring, i.e. Rzaand RTtogether are a C2 alkylene or alkenylene group, preferably a C2 alkylene group, more preferably a C2 alkylene group in which a CH2 group is replaced by a carbonyl group. Most preferably, Rzaand RTtogether are -CH2-C(=O)-.

[0202] In various embodiments, Rzcis H, Ci-Ce-alkyl, Cs-Ce-cycloalkyl, which are unsubstituted or substituted with halogen, phenyl, or -CFh-phenyl, wherein the rings are unsubstituted or substituted with Rf. In preferred embodiment, Rzcis H, Ci-Ce-alkyl, Ci-Ce-haloalkyl, or phenyl which is unsubstituted or substituted with Rf. In even more preferred embodiments, Rzcis H, CH3, C2H5, n-CsH?, isopropyl, CH2F, CHF2, CF3, CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2, CH2CF2CF3, or phenyl which is unsubstituted or substituted with Rf. In most preferred embodiments, Rzcis H or CH3, in particular H.

[0203] In various embodiments, Rzais H, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkylene-NRbRc, Ci-Ce- C(=O)-Rd, phenyl, phenylcarbonyl, or -CFh-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf.

[0204] In other embodiments, Rzais H, Ci-Ce-alkyl, or Ci-Ce-haloalkyl. In still other embodiments, Rzais H, Ci- Ce-alkyl. It is preferred that Rzacombines with RTto form a ring as described below.

[0205] In various embodiments, T is O. In such embodiments, Z is -NRZC-C(=O)-, -NRZC-C(=S)- or -N=C(S- Rza)-. 43

[0206] In various other embodiments, T is N. In such embodiments, Z is typically -NRzc-C(S-Rza)=.

[0207] In various other embodiments, T is N-RT. In such embodiments, Z is -NRZC-C(=O)-, -NRZC-C(=S)- or -N=C(S-Rza)-.

[0208] In various preferred embodiments, T is N or N-RT, depending on the identity of Z. If Z is -NRZC-C(=O)- , -NRZC-C(=S)- or -N=C(S-Rza)-, T is preferably N-RT. If Z is -NRzc-C(S-Rza)=, T is N.

[0209] In various embodiments, RTis H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-C4-alkyl-Ci-Ce-alkoxy, which are unsubstituted or substituted with halogen. In preferred embodiments, RTis H or Ci-Ce-alkyl.

[0210] In another embodiment, in particular if Z is -NRzc-C(S-Rza)=, Rzctogether with RTforms a linear Ci-Ce- alkylene or a linear C2-C6-alkenylene group, where in the linear Ci-Ce-alkylene and the linear C2-C6- alkenylene a CH2 moiety may be replaced by a carbonyl or a C=N-Rband / or wherein 1 or 2 CH2 moieties may be replaced by O or S and / or wherein the linear Ci-Ce-alkylene and the linear C2-C6-alkenylene may be unsubstituted or substituted with Rh. In such embodiments, Rzctogether with RTforms Ci-Ce- alkylene or a linear C2-Ce-alkenylene group, where in the linear Ci-Ce-alkylene and the linear C2-C6- alkenylene a CH2 moiety is replaced by a carbonyl group.

[0211] In various preferred embodiments, Rzatogether with RTforms a linear Ci-Ce-alkylene or a linear C2-C6- alkenylene group, where in the linear Ci-Ce-alkylene and the linear C2-Ce-alkenylene a CH2 moiety may be replaced by a carbonyl or a C=N-Rband / or wherein 1 or 2 CH2 moieties may be replaced by O or S and / or wherein the linear Ci-Ce-alkylene and the linear C2-C6-alkenylene may be unsubstituted or substituted with Rh. In more preferred embodiments thereof, Rzatogether with RTforms Ci-Ce-alkylene or a linear C2-C6-alkenylene group, where in the linear Ci-Ce-alkylene and the linear C2-C6-alkenylene a CH2 moiety is replaced by a carbonyl group. In another more preferred embodiment, Rzatogether with RTforms Ci-Ce-alkylene or a linear C2-C6-alkenylene group, where in the linear Ci-Ce-alkylene and the linear C2-C6-alkenylene a CH2 moiety is replaced by a C=N-Rband wherein 1 or 2 CH2 moieties may be replaced by O or S and / or wherein the linear Ci-Ce-alkylene and the linear C2-C6-alkenylene may be unsubstituted or substituted with Rh. In another more preferred embodiment, Rzatogether with RTforms Ci-Ce-alkylene or a linear C2-C6-alkenylene group, where in the linear Ci-Ce-alkylene and the linear C2- Cs-alkenylene 1 or 2 CH2 moieties are replaced by O or S and / or wherein the linear Ci-Ce-alkylene and the linear C2-C6-alkenylene may be unsubstituted or substituted with Rh. Most preferably, the formed ring is a 5-membered ring, i.e. Rzaand RTtogether are a C2 alkylene or alkenylene group, preferably a C2 alkylene group, more preferably a C2 alkylene group in which a CH2 group is replaced by a carbonyl group. Most preferably, Rzaand RTtogether are -CH2-C(=O)-.

[0212] In various embodiments, Ra, Rband Rcare H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, which are unsubstituted or substituted with halogen, Ci-Ce-alkylene-CN, phenyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf. 44

[0213] In preferred embodiments, Ra, Rband Rcare H, Ci-Ce-alkyl, C2-C6-alkenyl, C2-Ce-alkynyl, which are unsubstituted or substituted with halogen, phenyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf.

[0214] In various embodiments, Rdis H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, which are unsubstituted or substituted with halogen, phenyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf. In preferred embodiments, Rdis H, Ci-Ce-alkyl, Ci-Ce-haloalkyl, or phenyl which is unsubstituted or substituted with Rf.

[0215] In various embodiments, Reis Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, phenyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf. In preferred embodiment, Reis H, Ci-Ce-alkyl, Ci-Ce-haloalkyl, or phenyl unsubstituted or substituted with Rf.

[0216] In various embodiments, Rfis halogen, N3, OH, CN, NO2, -SON, -SF5, Ci-Ce-alkyl, Ci-Ce-alkoxy, C2-C6- alkenyl, C2-Ce-alkynyl, Cs-Ce-cycloalkyl, Cs-Ce-cycloalkoxy, which are unsubstituted or substituted with halogen, C(=O)-ORa, NRbRc, Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, C(=O)-NRbRc, C(=O)-Rd, SO2NRbRc, or S(=O)mRe. In preferred embodiments, Rfis halogen, N3, OH, CN, Ci-Ce-alkyl, Ci-Ce- alkoxy, 02-Ce-alkenyl, 02-Ce-alkynyl, Cs-Ce-cycloalkyl, Cs-Ce-cycloalkoxy, which are unsubstituted or substituted with halogen, C(=O)-ORa, NRbRc, Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, C(=O)-NRbRc, C(=O)-Rd, SO2NRbRc, or S(=O)mRe.

[0217] In various embodiments, R9is halogen, N3, OH, CN, NO2, -SCN, -SF5, Ci-Ce-alkyl, Ci-Ce-alkoxy, 02-Ce- alkenyl, 02-Ce-alkynyl, Cs-Ce-cycloalkyl, Cs-Ce-cycloalkoxy, which are unsubstituted or substituted with halogen, C(=O)-ORa, NRbRc, Ci-C6-alkylene-NRbRc, NH-Ci-C6-alkylene-NRbRc, C(=O)-NRbRc, C(=O)- Rd, SO2NRbRc, or S(=O)mRe. In preferred embodiments, R9is halogen, N3, OH, CN, NO2, Ci-Ce-alkyl, Ci-Ce-alkoxy, 02-Ce-alkenyl, Cs-Ce-cycloalkyl, Cs-Ce-cycloalkoxy, which are unsubstituted or substituted with halogen, C(=O)-ORa, NRbRc, Ci-C6-alkylene-NRbRc, C(=O)-NRbRc, C(=O)-Rd, SO2NRbRc, or S(=O)mRe.

[0218] In various embodiments, Rhis halogen, OH, Ci-Ce-alkyl, Cs-Ce-cycloalkyl, or CN.

[0219] In various embodiments, m is 0. In various embodiments, m is 1. In various embodiments, m is 2. In various embodiments, m is 0 or 1 . In various embodiments, m is 1 or 2.

[0220] In various embodiments, the structure Y-Z-T may be any one of formulas Y-1 to Y-10 wherein denotes attachment to X, D is R4and wherein RT, Rya, Ryc, Rzaand Rzcare as defined herein above. 45

[0221] In various embodiments, X is either a single bond, -CH2-CH2-, -CH(CH3)- or -CH(CH3)NRXC-, -CH2-NRXC- wherein Rxcis preferably H or methyl.

[0222] In various embodiments, Y-Z-T is Y-5. In various embodiments, Y-Z-T is Y-7. In various embodiments, Y-Z-T is Y-8. In various embodiments, Y-Z-T is Y-9. In various embodiments, Y-Z-T is Y-10.

[0223] In various embodiments, Y-Z-T is Y-5 and X is a single bond.

[0224] In various embodiments, Y-Z-T is Y-7 and X is a single bond or is -CH2-CH2- or -CH(CH3)NRXC-.

[0225] In various embodiments, Y-Z-T is Y-9 and X is -CH(CH3)- or -CH(CH3)NXC-.

[0226] In various embodiments, Y-Z-T is Y-5, X is a single bond and Ryais H.

[0227] In various embodiments, Y-Z-T is Y-7 and X is a single bond or is -CH2-CH2- and Rycis H. In various embodiments, Y-Z-T is Y-7 and X is -CH(CH3)NRXC- or is -CH2-NRXC- and Rycis H and Rxcis H or methyl.

[0228] In various embodiments, Y-Z-T is Y-9 and X is -CH(CH3)- and Rycis NH2 and Rzcand RTare H.

[0229] In various embodiments, Y-Z-T is Y-9 and X is -CH(CH3)NXC- and Ryc, Rzcand RTare H and Rxcis H or methyl.

[0230] In various embodiments, X is a single bond, Y is -CRya=N-, wherein the N is bound to Z, Z is -N=C(S- Rza)-, wherein T is bound to the carbon atom, and T is N-RT, wherein Rzatogether with RTforms a linear Ci-Ce-alkylene group, where in the linear Ci-Ce-alkylene a CH2 moiety is replaced by a carbonyl and wherein the linear Ci-Ce-alkylene is unsubstituted or substituted with Rh, and Ryais preferably H. 46

[0231] In various embodiments, X is a single bond, Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is - N=C(S-Rza)-, wherein T is bound to the carbon atom, and T is N-RT, wherein Rzatogether with RTforms a linear Ci-Ce-alkylene group, where in the linear Ci-Ce-alkylene a CH2 moiety is replaced by a carbonyl and wherein the linear Ci-Ce-alkylene is unsubstituted or substituted with Rh, and Rycis preferably H; or

[0232] In various embodiments, X is -(C(Rxa)2)P-, wherein p is 2, Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is -N=C(S-Rza)-, wherein T is bound to the carbon atom, and T is N-RT, wherein Rzatogether with RTforms a linear Ci-Ce-alkylene group, where in the linear Ci-Ce-alkylene a CH2 moiety is replaced by a carbonyl and wherein the linear Ci-Ce-alkylene is unsubstituted or substituted with Rh, and all Rxaand Rycare preferably H.

[0233] In various embodiments, X is -(C(Rxa)2)o-NRxc-, wherein 0 is 1 and N is bound to Y, Y is -NRyc-C(=O)- , wherein C(=O) is bound to Z, Z is -N=C(S-Rza)-, wherein T is bound to the carbon atom, and T is N- RT, wherein Rzatogether with RTforms a linear Ci-Ce-alkylene group, where in the linear Ci-Ce-alkylene a CH2 moiety is replaced by a carbonyl and wherein the linear Ci-Ce-alkylene is unsubstituted or substituted with Rh, and one Rxa, Rxcand Rycare preferably H and the other Rxais preferably methyl.

[0234] In various embodiments, X is -(C(Rxa)2)o-NRxc-, wherein 0 is 1 and N is bound to Y, Y is -NRyc-C(=O)- , wherein C(=O) is bound to Z, Z is -NRZC-C(=S)-, wherein C(=S) is bound to T, and T is N-RT, wherein one Rxa, Rxc, Ryc, Rzcand RTare preferably H and the other Rxais preferably methyl.

[0235] In various embodiments, X is -(C(Rxa)2)P-, wherein p is 1 , Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is -NRZC-C(=S)-, wherein C(=S) is bound to T, and T is N-RT, wherein one Rxa, Rzcand RTare preferably H, the other Rxais preferably methyl, and Rycis preferably -NH2.

[0236] In various embodiments, X is X is -(C(Rxa)2)o-NRxc-, wherein 0 is 1 and N is bound to Y, Y is -NRyc- C(=O)-, wherein C(=O) is bound to Z, Z is -NRZC-C(=S)-, wherein C(=S) is bound to T, and T is N-RT, wherein one Rxa, Ryc, Rzcand RTare preferably H and the other Rxaand Rxcare preferably methyl.

[0237] In various embodiments, X is -(C(Rxa)2)o-NRxc-, wherein 0 is 1 and N is bound to Y, Y is -NRyc-C(=O)- , wherein C(=O) is bound to Z, Z is -N=C(S-Rza)-, wherein T is bound to the carbon atom, and T is N- RT, wherein Rzatogether with RTforms a linear Ci-Ce-alkylene group, preferably C2 alkylene group, where in the linear Ci-Ce-alkylene a CH2 moiety is replaced by a carbonyl and wherein the linear Ci-Ce- alkylene is unsubstituted or substituted with Rh, and one Rxaand Rycare preferably H and the other Rxaand Rxcare preferably methyl.

[0238] In one preferred embodiment, R4is aryl, aryl-Ci-C4-alkyl, hetaryl, or hetaryl-Ci-C4-alkyl, wherein the aryl or hetaryl rings are unsubstituted or substituted with one or more R9and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9- or 10-membered bicyclic hetaryl. The aryl may be 6- membered monocyclic aryl, i.e. phenyl, a 10-membered bicyclic aryl, i.e. naphthyl, or a 12-membered tricyclic aryl. 47

[0239] In preferred embodiments, R4is aryl, aryl-Ci-C4-alkyl, hetaryl, or hetaryl-Ci-C4-alkyl, wherein the rings are unsubstituted or substituted with one or more R9and where hetaryl in hetaryl or hetaryl-Ci-C4-alkyl, is preferably a 5- or 6-membered monocyclic hetaryl such as pyridyl, pyrimidinyl, pyridazinyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl or isothiazolyl which is unsubstituted or substituted with one or more R9and where aryl is preferably naphthyl or phenyl, more preferably phenyl which is unsubstituted or substituted with one or more R9.

[0240] In preferred embodiments, R4is aryl or hetaryl-Ci-C4-alkyl, wherein the rings are unsubstituted or substituted with one or more R9and where hetaryl in hetaryl or hetaryl-Ci-C4-alkyl, is preferably a 5- or 6-membered monocyclic hetaryl such as pyridyl which is unsubstituted or substituted with one or more R9and where aryl is preferably naphthyl or phenyl, more preferably phenyl which is unsubstituted or substituted with one or more R9.

[0241] In various embodiments, R9is one, two or three substituents. Each R9may be independently selected from halogen, N3, OH, CN, NO2, -SON, -SF5, Ci-Ce-alkyl, Ci-Ce-alkoxy, C2-Ce-alkenyl, tri-Ci-Ce- alkylsilyl, C2-Ce-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkoxy-Ci-C4-alkoxy, Cs-Ce-cycloalkyl, C3-C6- cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(=O)-ORa, NRbRc, Ci-C6-alkylene-NRbRc, O-Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, NH-CI-C6- alkylene-NRbRc, C(=O)-NRbRc, C(=O)-Rd, SO2NRbRc, and S(=O)mRe.

[0242] In various preferred embodiments, each R9is independently selected from halogen, preferably F or Cl, Ci-Ce-alkyl, Ci-Ce-alkoxy, Ci-Ce-alkoxy-Ci-C4-alkyl, Ci-Ce-alkoxy-Ci-C4-alkoxy, Cs-Ce-cycloalkyl, C3- Ce-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, NRbRc, Ci-Ce-alkylene-NRbRc, O-Ci-Ce-alkylene-NRbRc, and C(=O)-NRbRc. In further embodiments, each R9is independently selected from F, Cl, Ci-Ce-alkyl, Ci-Ce-alkoxy, Ci-Ce-alkoxy-Ci-C4-alkyl, wherein the alky and alkoxy moieties are unsubstituted or substituted with halogen, preferably F, and NRbRc, wherein Rband Rcare preferably Ci-Ce-alkyl, for example methyl. In such embodiments, R9may be Ci-Ce-alkyl which may be selected from methyl and isopropyl or may be Ci-Ce-alkoxy-Ci-C4- alkyl substituted with halogen, such as ethoxymethyl substituted with halogen, such as 2,2,2- trifluoroethoxymethyl.

[0243] In various embodiments, where R4is aryl, in particular phenyl, it is substituted with at least one R9, said R9being preferably in the ortho position relative to the attachment point. If there are two R9substituents, these are preferably in the two ortho positions or one is in the ortho position and the other in the para or meta (2,5-substituted) position. If there are three R9substituents, these are preferably in the two ortho and in the para position. 48

[0244] In various embodiments, R4is selected from the following groups:

[0245] In various embodiments, R4is any one of R4-1 , R4-29, R4-30 and R4-31 .

[0246] In various embodiments, R1may be selected from the following groups: 49 wherein # indicates the point of attachment. R4is defined as above and is preferably selected any one of R4-1 , R4-29, R4-30 and R4-31 .

[0247] In various embodiments, the compound of formula (I) is selected from any one of the following: 50 51 52 53 54 55 56 57 58 59 60 61 62

[0248] 63 64 65 or an N-oxide, stereoisomer, tautomer, agriculturally or veterinarily acceptable salt thereof.

[0249] All the above disclosed R1, R2and R3are also individual embodiments of the invention and can be combined with respective other R1, R2and R3groups. For example, the option of R3being 3,4- dichlorophenyl, 4-cyanophenyl or 4-ethoxyphenyl may be combined with all other compound of formula (I) definitions disclosed herein. Alternatively, R2may be 3,4-dichlorophenyl, 4-cyanophenyl or 4- ethoxyphenyl and R3is H or methyl.

[0250] Mixtures

[0251] The invention also relates to a mixture of at least one compound of the invention with at least one mixing 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 equal amounts, or an excess of component I, or an excess of component II may be used.

[0252] Mixing partners can be selected from pesticides, in particular insecticides, nematicides, and acaricides, fungicides, herbicides, plant growth regulators, fertilizers. Preferred mixing partners are insecticides, nematicides, and fungicides.

[0253] The following list M of pesticides, grouped according the Mode of Action Classification of the Insecticide Resistance Action Committee (IRAC), together with which the compounds of the invention can be used and with which potential synergistic effects might be produced, illustrates the possible combinations:

[0254] 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;

[0255] M.2. GABA-gated chloride channel antagonists: cyclodiene organochlorine compounds: endosulfan, chlordane; phenylpyrazoles: ethiprole, fipronil, flufiprole, pyrafluprole, pyriprole; 66

[0256] M.3 Sodium channel modulators: pyrethroids: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, 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, 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;

[0257] M.4 nAChR agonists: neonicotinoids: acetamiprid, clothianidin, cycloxaprid, dinotefuran, im-idacloprid, nitenpyram, thiacloprid, thiamethoxam; 4,5-dihydro-N-nitro-1-(2-oxiranylmethyl)-1 H-imidazol-2-amine, (2E-)-1-[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; 1 -[(6-

[0258] Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 ,2,3,5,6,7-hexahydroimidazo[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;

[0259] M.5 Nicotinic acetylcholine receptor allosteric activators:spinosyns, e.g. spinosad or spineto-ram;

[0260] M.6 Chloride channel activators from the class of avermectins and milbemycins, e.g. abamectin, emamectin benzoate, ivermectin, lepimectin, or milbemectin;

[0261] M.7 Juvenile hormone mimics, such as hydroprene, kino-prene, methoprene; fenoxycarb, or pyriproxyfen;

[0262] M.8 miscellaneous multi-site inhibitors: CHsBr, other alkyl halides, chloropicrin, sulfuryl fluoride, borax, tartar emetic;

[0263] M.9 Chordotonal organ TRPV channel modulators: afidopyropen, pymetrozine; pyrifluquinazon;

[0264] M.10 Mite growth inhibitors: clofentezine, hexythiazox, diflovidazin, etoxazole;

[0265] 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, bacillus thuringiensis subsp. tenebrionis, Bt crop proteins: CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1 ; 67

[0266] M.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron, organotin miticides, e.g.: azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;

[0267] M.13 Uncouplers of oxidative phosphorylation via disruption ofthe proton gradient: chlorfenapyr, DNOC, sulfluramid;

[0268] M.14 nAChR channel blockers: nereistoxin analogues bensultap, cartap hydrochloride, thio-cyclam, thiosultap-sodium;

[0269] M.15 Inhibitors of the chitin biosynthesis type 0, e.g.: bistrifluron, chlorfluazuron, difluben-zuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;

[0270] M.16 Inhibitors of the chitin biosynthesis type 1 : buprofezin;

[0271] M.17 Moulting disruptors: Dipteran, cyromazine;

[0272] M.18 Ecdyson receptor agonists, e.g.: methoxyfenozide, tebufenozide, halofenozide, fufeno-zide, chromafenozide;

[0273] M.19 Octopamin receptor agonists: amitraz;

[0274] M.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon, acequinocyl, fluacrypyrim; bifenazate;

[0275] M.21 METI acaricides and insecticides, e.g.: fenazaquin, fen pyroxi mate, pyrimidifen, pyrida-ben, tebufenpyrad, tolfenpyrad, rotenone;

[0276] M.22 Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone, 2-[2-(4-cyanophenyl)- 1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazine carboxamide, N-(3- chloro-2-methylphenyl)-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)-1 H-pyrazole-5-carboxamide, 2-[2-(4-cyanophenyl)-1-[3-

[0277] (trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide;

[0278] 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; 68

[0279] M.24 Mitochondrial complex IV electron transport inhibitors: e.g. aluminium phosphide, calcium phosphide, zinc phosphide, cyanide;

[0280] M.25 Mitochondrial complex II electron transport inhibitors, e.g.: cyenopyrafen, cyflumetofen, cyetpyrafen, pyflubumide;

[0281] M.26 Ryanodine receptor-modulators: chlorantraniliprole, cyantraniliprole, cyclanili prole, flubendiamide, fluchlordiniliprole, (R)-3-chloro-N1-{2-methyl-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)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)phthalamide, methyl-2-[3,5-dibromo- 2-({[3-bromo-1-(3-chlorpyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1 ,2-dimethylhydrazine- carboxylate; N-[2-(5-amino-1 ,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2- py rid i ny I)- 1 H-pyrazole-5-carboxamide; 3-chloro-1 -(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1 -cyano-1 - methylethyl)amino]carbonyl]phenyl]-1 H-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)-1 H-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)-1 H-pyrazole-5-carboxamide, pixoaniliprole;

[0282] M.27: Chordotonal organ Modulators: flonicamid;

[0283] M.28: broflanilide; fluxametamide, isocycloseram, piperflanilide;

[0284] M.29 acynonapyr;

[0285] 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, 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, 4-cyano-N-[2-cyano-5-[[[2,6- dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]phenyl]-2-methyl- benzamide, 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1- (trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide, N-[5-[[[2-chloro-6-cyano-4-[1 ,2,2,3,3,3-hexafluoro- 1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide, N-[5- [[[2-bromo-6-chloro-4-[2, 2, 2-trifluoro-1 -hydroxy-1 -(trifluoro-methyl)ethyl]phenyl]amino]carbonyl]-2- cyano-phenyl]-4-cyano-2-methyl-benzamide, N-[5-[[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1- (trifluoromethyl)propyl]phenyl]amino]carbonyl]-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]amino]carbonyl]phenyl]-2-methyl-benzamide, 1-[2-fluoro-4-methyl-5- 69

[0286] [(2,2,2-trifluoro-ethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4-triazole-5-amine, N-[5-[[[2-bromo-6- chloro-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano- 2-methyl-benzamide, 4-cyano-N-[2-cyano-5-[[[2,6-dichloro-4-[1 ,2,2,2-tetrafluoro-1 -

[0287] (trifluoromethyl)ethyl]phenyl]amino]carbonyl]phenyl]-2-methyl-benzamide, actives on basis of bacillus firmus (Votivo, 1-1582); fluazaindolizine; 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)-phenoxy]propoxy]- 1 H-pyrazole; N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)-propyl]phenyl]- 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 - (trifluoromethyl)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;

[0288] 2-(1 ,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; 2-[6-[2-(5-fluoro-3-pyridinyl)-5-thiazolyl]-2- pyridinyl]-pyrimidine; 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; N-methylsulfonyl-6-[2-(3- pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2- carboxamide; 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; N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)[4-

[0289] [methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide; 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)-1 H-pyrazole-5-carboxamide; N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1- methyl-3-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1 H-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-

[0290] (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-(trifluoromethyl)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-

[0291] (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-(trifluoromethoxy)phenyl]-1 ,2,4-triazol-

[0292] 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]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]phenyl]methylenehydrazono]thiazolidin-4-one; 2-(6-chloro-3-ethylsulfonyl-imidazo[1 ,2-a]pyridin-2-yl)- 70

[0293] 3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1 ,2-a]pyridin-2- yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-6-iodo-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]pyridin- 2-yl)-3-methyl-6-(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-(3-ethylsulfonyl-7-iodo-imidazo[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-(trifluoromethyl)imidazo[4,5-b]pyridine,

[0294] 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1 ,2-a]pyridin-2-yl]-3-methyl-6-

[0295] (trifluoromethylsulfinyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1 ,2- a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine, 2-(6-bromo-3-ethylsulfonyl- imidazo[1 ,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-c]pyridine; N-[[2-fluoro-4-[(2S,3S)-2-hydroxy-

[0296] 3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl]methyl]cyclopropanecarboxamide; sulfiflumin; flupentiofenox, N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-2-methylsulfonyl-propanamide, cyclobutrifluram; N-[4-chloro-3-[(1-cyanocyclopropyl)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, N-[4-chloro-2-(3- pyridyl)thiazol-5-yl]-N-ethyl-3-methylsulfonyl-propanamide, 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-

[0297] 4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(pyrimidin-2-ylmethyl)isoquinoline-8- carboxamide, N-[1 -(2,6-difluorophenyl)pyrazol-3-yl]-2-(trifluoromethyl)benzamide, 5-((1 R,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-[(1 S)-1 -[1 -[6-(trifluoromethyl)-4-pyrimidinyl]-1 H-1 , 2 ,4-triazo l-5-y l]ethy I]- 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[8.4.0.0A{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, 2-(5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-5-

[0298] (trifluoromethylsulfinyl)-l ,3-benzoxazole, isoflualanam.

[0299] The commercially available compounds M listed above may be found in The Pesticide Man-ual, 18th Edition, C. MacBean, British Crop Protection Council (2018), or http: / / bcpcdata.com / pesticide- manual.html, http: / / www.alanwood.net / pesticides.

[0300] The active compounds described by IUPAC nomenclature are known from CN103814937; WO2013 / 003977, W02007 / 101369, WO2018 / 177970, CN10171577, CN102126994, W02007 / 101540, W02007 / 043677, WO2011 / 085575, W02008 / 134969, WO2012 / 034403, W02006 / 089633, 71

[0301] W02008 / 067911 , W02006 / 043635, W02009 / 124707, WO2013 / 050317, WO2010 / 060379,

[0302] WO2010 / 127926, WO2010 / 006713, WO2012 / 000896, W02007 / 101369, WO2012 / 143317,

[0303] WO2015 / 038503, EP2910126, WO2015 / 059039, W02015 / 190316, WO2012 / 126766,

[0304] W02009 / 102736, WO2013 / 116053, WO2018 / 052136, WO2015150252, W02020055955,

[0305] WO2021158455, WO2013092350, WO201811111 , EP3608311 , WO2019236274, WO2013092350, WO 2018052136, W02009102736, WO2016174049, WO2012126766, CN106554335,

[0306] WO2017054524, CN105153113, W02022072650; WO2018071327, W02022101502,

[0307] WO2012158396, W02007079162, W02020013147, W02020097414, EP242081 , WO2023058748, WO2017065228, EP3428166, WO2021029308, W02022009058, WO2017067500, W02020090585, WO2017146226, W02021043115, WO2023016278.

[0308] The following list of fungicides, in conjunction with which the compounds of the invention can be used, illustrates the possible combinations:

[0309] A) Respiration (C) complex III at Qosite (Qol, C3): azoxystrobin (A.1.1), bifujunzhi (A.1.37), coumethoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), famoxadone (A.1.21), fenamidone (A.1.21), fenaminstrobin (A.1.6), flufenoxystrobin (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- allylideneaminooxymethyl)-phenyl)-2-methoxyimino-A / -methyl-acetamide (A.1.18), methyl- A / -[2-[(1 ,4-dimethyl-5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-A / -methoxy-carbamate (A.1 .22),

[0310] (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-A / ,3-dimethyl-pent-3-enamide (A.1 .34), (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-A / ,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-2-enoate, methyl (Z)-3-methoxy- 2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1 -yl]phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-

[0311] 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)-

[0312] 2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclobutyl-2-methyl-phenoxy)-

[0313] 3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclopropyl-2-methyl-phenoxy)-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-[(2-methyl-5-phenyl-phenyl)methyl]prop-

[0314] 2-enoate; methyl (E)-3-methoxy-2-[[5-[(E)- / V-methoxy-C-methyl-carbonimidoyl]-2,4-dimethyl- phenyl]methyl]prop-2-enoate; methyl (E)-2-[[5-(2-cyclopropylethynyl)-2,4-dimethyl-phenyl]methyl]-

[0315] 3-methoxy-prop-2-enoate; methyl (E)-3-methoxy-2-(2-phenyl-1 ,3-benzoxazol-4-yl)prop-2-enoate; 72 methyl (E)-3-methoxy-2-(2-phenyl-1 ,3-benzothiazol-4-yl)prop-2-enoate; methyl (E)-3-methoxy-

[0316] 2-(2-phenyl-1 ,3-benzoxazol-7-yl)prop-2-enoate; methyl (Z)-2-[6-(2-cyclopropylethynyl)benzimidazol- 1 -yl]-3-methoxy-prop-2-enoate; methyl (Z)-3-methoxy-2-(6-phenylbenzimidazol-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-

[0317] 2-[6-[(E)-methoxyiminomethyl]indol-1 -yl]prop-2-enoate; methyl (Z)-3-methoxy-2-[6-[(E)- / V-methoxy-

[0318] C-methyl-carbonimidoyl]indol-1 -yl]prop-2-enoate, methyl (E)-2-[4-chloro-2-(4-methylpent- 1 -ynyl)phenyl]-3-methoxy-prop-2-enoate, methyl (E)-3-methoxy-2-[4-methoxy-2-(4-methylpent-

[0319] 1 -ynyl)phenyl]prop-2-enoate, methyl (E)-2-(4-chloro-2-hex-1 -ynyl-phenyl)-3-methoxy-prop-2-enoate, methyl (E)-2-(2-hex-1 -ynyl-4-methoxy-phenyl)-3-methoxy-prop-2-enoate, methyl

[0320] (E)-2-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-6-methyl-phenyl]-3-methoxy-prop-2-enoate, methyl (2E)-2-[2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-6-methyl-phenyl]-2-methoxyimino-actate, (2E)-2-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-6-methyl-phenyl]-2-methoxyimino-A / -methyl- acetamide, methyl (E)-2-[2-[[(E)-1 -(4-chlorophenyl)ethylideneamino]oxymethyl]-6-methyl-phenyl]-

[0321] 3-methoxy-prop-2-enoate, methyl (E)-3-methoxy-2-[2-methyl-

[0322] 6-[[(E)-1-[4-(trifluoromethyl)phenyl]ethylideneamino]oxymethyl]phenyl]prop-2-enoate, methyl

[0323] (E)-2-[4-chloro-2-[[(E)-1-(4-chlorophenyl)ethylideneamino]oxymethyl]phenyl]-3-methoxy-prop-

[0324] 2-enoate, methyl (E)-2-[2-chloro-6-[[(E)-1 -(4-chlorophenyl)ethylideneamino]oxymethyl]phenyl]-

[0325] 3-methoxy-prop-2-enoate, methyl / V-[[5-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-3-yl]-2-methyl- phenyl]methyl]carbamate, methyl / V-[[5-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl- phenyl]methyl]carbamate; complex III at Qi site (Qil, C4): cyazofamid (A.2.1), amisulbrom (A.2.2), [(6S,7R,8R)-8-benzyl-

[0326] 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), A / -[2-[2-chloro-

[0327] 4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide

[0328] (A.3.29), methyl (E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate

[0329] (A.3.30), 2-(difluoromethyl)- / V-(1 ,1 ,3-trimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.32),

[0330] 2-(difluoromethyl)- / V-[(3 / ?)-1 ,1 ,3-trimethylindan-4-yl]pyridine-3-carboxamide (A.3.33),

[0331] 2-(difluoromethyl)- / V-(3-ethyl-1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.34),

[0332] 2-(difluoromethyl)- / V-[(3 / ?)-3-ethyl-1 ,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.35),

[0333] 2-(difluoromethyl)- / V-(1 ,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide (A.3.36),

[0334] 2-(difluoromethyl)- / V-[(3 / ?)-1 ,1-dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide (A.3.37),

[0335] 2-(difluoromethyl)- / V-(3-isobutyl-1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.38),

[0336] 2-(difluoromethyl)- / V-[(3 / ?)-3-isobutyl-1 ,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.39); 73 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);

[0337] ATP transport: silthiofam (A.4.11); quinone inside and outside inhibitor stigmatellin binding type (QioSI; C8): ametoctradin (A.5.1);

[0338] B) Sterol biosynthesis (G)

[0339] 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), imibenconazole (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)-

[0340] 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)-

[0341] 1 ,1-difluoro-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile (B.1 .53),

[0342] 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol (B.1 .54),

[0343] 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol (B.1 .55),

[0344] (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 , 2 ,4-triazo I- 1 -yl)propan-2-ol,

[0345] (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 , 2 ,4-triazo I- 1 -yl)propan-2-ol, methyl

[0346] 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propanoate (B.1 .56),

[0347] 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propanoic acid (B.1 .57); imidazoles: 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 (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);

[0348] 3-keto reductase (G3): fenhexamid (B.3.1), fenpyrazamine (B.3.2); other: chlorphenomizole (B.4.1);

[0349] C) Nucleic acids metabolism (A)

[0350] 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); 74 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-chlorophenylmethoxy)pyrimidin-4-amine (C.2.8);

[0351] 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), fenaptamidoquin (C.5.3);

[0352] 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), A / -ethyl-2-[(3-ethynyl- 8-methyl-6-quinolyl)oxy]butanamide (D.1 .8), A / -ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- 2-methylsulfanyl-acetamide (D.1 .9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- / V-(2-fluoroethyl)butanamide (D.1 .10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- / V-(2-fluoroethyl)-2-methoxy-acetamide (D.1 .11), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- / V-propyl-butanamide (D.1 .12), 2-[(3-ethynyl-8-methyl- 6-quinolyl)oxy]-2-methoxy- / V-propyl-acetamide (D.1 .13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- 2-methylsulfanyl- / V-propyl-acetamide (D.1 .14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- / V-(2-fluoroethyl)- 2-methylsulfanyl-acetamide (D.1 .15), 4-(2-bromo-4-fluoro-phenyl)- / V-(2-chloro-6-fluoro-phenyl)- 2,5-dimethyl-pyrazol-3-amine (D.1 .16), 4-(2-bromo-4-fluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-

[0353] 1 .3-dimethyl-1 / 7-pyrazol-5-amine, 4-(2-chloro-4,6-difluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-

[0354] 1 .3-dimethyl-1 / 7-pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-3-ethyl-

[0355] 1-methyl-1 / 7-pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)- / V-(2-fluoro-4-methyl-6-nitrophenyl)-

[0356] 1 .3-dimethyl-1 / 7-pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-1 ,3-dimethyl- 1 / 7-pyrazol-5-amine, 4-(2,4-difluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-1 ,3-dimethyl-1 / 7-pyrazol- 5-amine; tubulin polymerization (B2): diethofencarb (D.2.1), tubulin polymersation (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); actin / myosin / fimbrin function (B6): metrafenone (D.2.6), phenamacril (D.2.8), pyriofenone (D.2.7);

[0357] 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);

[0358] F) Signal transduction 75 mechanism unknown (E1): proquinazid (F.2.2), quinoxyfen (F.2.1);

[0359] MAP / histidine kinase os-2 (E2): fludioxonil (F.1 .5);

[0360] MAP / histidine kinase os-1 (E3): iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4);

[0361] G) Lipid synthesis or transport I 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-(difluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]-A / -tetralin-1-yl-pyridine-

[0362] 2-carboxamide (G.5.4), 4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]- / V-tetralin-1-yl- pyridine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]- 4-piperidyl]- / V-tetralin-1-yl-pyridine-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-

[0363] 3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]- / V-tetralin-1-yl-pyridine-2-carboxamide (G.5.7),

[0364] 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-A / -tetralin-1-yl-pyridine-

[0365] 2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-

[0366] A / -tetralin-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]- 4-piperidyl]- / V-tetralin-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-

[0367] 3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-A / -tetralin-1-yl-pyridine-2-carboxamide (G.5.11),

[0368] (1-(4-(4-(5-(2,6-dichlorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)piperidin-1-yl)- 2-((3-trifluoromethyl)pyrazin-2-yl)oxy)ethan-1 -one, 1 -(4-(4-(5-(2-chloro-6-fluorophenyl)-

[0369] 4.5-dihydroisoxazol-3-yl)thiazol-2-yl)piperidin-1-yl)-2-((3-trifluoromethyl)pyridin-2-yl)oxy)ethan-1-one, te / Y-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)-1 / 7-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol-4-yl)-

[0370] 4.5-dihydroisoxazo-5-yl)-3-fluorophenyl)imino)dimethyl-A6-sulfanone, ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1 / 7-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol-4-yl)-

[0371] 4.5-dihydroisoxazo-5-yl)-3-fluorophenyl)imino)dimethyl-A6-sulfanone, ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1 / 7-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol-4-yl)-

[0372] 4.5-dihydroisoxazo-5-yl)-3-chorophenyl)imino)(isopropyl)(methyl)-A6-sulfanone, ((2-(3-(2-(1-(2-(3,5-bis(trifluoromethyl)-1 / 7-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol-4-yl)-

[0373] 4.5-dihydroisoxazo-5-yl)-3-fluorophenyl)imino)(isopropyl)(methyl)-A6-sulfanone, ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1 / 7-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol-4-yl)-

[0374] 4.5-dihydroisoxazo-5-yl)-3-(trifluoromethyl)phenyl)imino)dimethyl-A6-sulfanone, ((3-fluoro-

[0375] 2-(3-(2-(1-(2-(5-methyl-3-(trifluoromethyl)-1 / 7-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol-4-yl)-

[0376] 4.5-dihydroisoxazo-5-yl)-phenyl)imino)dimethyl-A6-sulfanone;

[0377] H) Multi Site Activity (M) 76 inorganics (M01): Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (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-1 / 7,5 / 7-[1 ,4]dithiino[2,3-c:5,6-c']dipyrrole- 1 ,3,5,7(2H,6H)-tetraone (H.4.10),

[0378] I) Cell wall biosynthesis (H) and melanin synthesis in cell wall (I) chitin synthase (H4): polyoxin B (1.1.2); cellulose synthase (H5): benthiavalicarb (1.3.5), dimethomorph (1.3.1), flumorph (1.3.2), iprovalicarb (1.3.6), mandipropamid (1.3.3), pyrimorph (1.3.4), valifenalate (1.3.7); reductase in melanin synthesis (MBI-R; 11) pyroquilon (1.2.1), tricyclazole (1.2.2); dehydratase in melanin synthesis (MBI-D, I2); carpropamid (1.2.3), dicyclomet (1.2.4), fenoxanil (I.2.5); polyketide synthase in melanin synthesis (MBI-P, I3): tolprocarb (1.2.6);

[0379] 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-cyclopropyl- A / -(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1 .10);

[0380] K) 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) [MoA proposed: 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); A / -(4-(4-chloro-3-trifluoromethyl-phenoxy)- 77

[0381] 2,5-dimethyl-phenyl)-A / -ethyl-A / -methyl formamidine (K.1.27), A / -(4-(4-fluoro-3-trifluoromethyl- phenoxy)-2,5-dimethyl-phenyl)-A / -ethyl-A / -methyl formamidine (K.1 .28),

[0382] A / -[4-[[3-[(4-chlorophenyl)methyl]-1 ,2,4-thiadiazol-5-yl]-oxy]-2,5-dimethyl-phenyl]-A / -ethyl-A / -methyl- formamidine (K.1 .29), A / -(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-A / -ethyl-A / -methyl-formamidine

[0383] (K.1.30), A / -[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-A / -ethyl-A / -methyl- formamidine (K.1.31), A / -[5-bromo-6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-A / -ethyl-A / -methyl- formamidine (K.1.32), A / -[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-A / -ethyl-A / -methyl- formamidine (K.1 .33), A / -(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-A / -ethyl-

[0384] / V-methyl formamidine (K.1 .34), A / -(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)- / V-ethyl- / V-methyl formamidine (K.1 .35), 2-(4-chloro-phenyl)-A / -[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]- 2-prop-2-ynyloxy-acetamide (K.1 .36), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (K.1.38), 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 / 7-benzoimidazole (K.1.39), ethyl

[0385] (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1 .40), pentyl A / -[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl- methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1 .42), but-3-ynyl A / -[6-[[(Z)-[(1-methyltetrazol- 5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1 .43), 2-(6-benzyl-

[0386] 2-pyridyl)quinazoline (K.1 .50), 2-[6-(3-fluoro-4-methoxy-phenyl)-5-methyl-2-pyridyl]-quinazoline (K.1 .51), A / -(2,5-dimethyl-4-phenoxy-phenyl)-A / -ethyl-A / -methyl-formamidine (K.1 .53), / V-[5-bromo- 2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-A / -ethyl-A / -methyl-formamidine (K.1.56), A / '-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-A / -ethyl-A / -methyl-formamidine (K.1.57), / V-methyl-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzenecarbothioamide (K.1 .59), / V-methoxy- A / -[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropane-carboxamide (K.1.61), / V-((4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl)methyl)propanamide (K.1 .62), 3,3,3-trifluoro- / V-[[3-fluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.63), 3,3,3-trifluoro- / V-[[2-fluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl] propanamide

[0387] (K.1 .64), / V-[2,3-difluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzyl]-butanamide (K.1.65), / V-[[2,3-difluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propanamide

[0388] (K.1.66), 1 -methoxy-1 -methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea

[0389] (K.1.67), 1 , 1 -diethyl-3-[[4-[5-[trifluoromethyl]-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.68),

[0390] / V,2-dimethoxy- / V-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.69),

[0391] / V-ethyl-2-methyl- / V-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.70),

[0392] 1 -methoxy-3-methyl-1 -[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.71),

[0393] 1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.72),

[0394] 1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one (K.1.73),

[0395] 4-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]morpholin-3-one (K.1.74), 4.4-dimethyl-

[0396] 2-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.75),

[0397] 2-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.76), 5.5-dimethyl-

[0398] 2-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.77), 3.3-dimethyl-

[0399] 1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one (K.1.78),

[0400] 2-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]oxazinan-3-one (K.1.79), 1 -[[3-fluoro-

[0401] 4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one (K.1.80), 4.4-dimethyl- 78

[0402] 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), / V-methyl-

[0403] 1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1 .84),

[0404] / V, / V-dimethyl-1-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzyl]-1 / 7-1 ,2,4-triazol-3-amine (K.1 .85),

[0405] / V-methoxy- / V-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), / V-methoxy-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-

[0406] 3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1 .88), / V-allyl- / V-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol- 3-yl]phenyl]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-

[0407] 3-yl]phenyl]methyl]urea (K.1 .91), / V-allyl- / V-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-

[0408] 3-yl]phenyl]methyl]acetamide (K.1 .92), / V-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-

[0409] 3-yl]benzyl]cyclopropanecarboxamide (K.1 .93), 1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-

[0410] 3-yl]phenyl]methyl]urea (K.1.94), A / '-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-A / -ethyl-A / -methyl- formamidine (K.1 .95), / W[2-chloro-4-[(4-methoxy-phenyl)methyl]-5-methyl-phenyl]- / V-ethyl- / \ / -methyl- formamidine (K.1 .96), A / '-[2-chloro-4-[(4-cyano-phenyl)methyl]-5-methyl-phenyl]-A / -ethyl-A / -methyl- formamidine (K.1 .97), A / '-[2,5-dimethyl-4-(o-tolylmethyl)phenyl]-A / -ethyl-N-methyl-formamidine (K.1 .98), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-A / -[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl- pyridazine-4-carboxamide (K.1 .99), 3-(3-bromo-2-fluoro-phenoxy)-6-chloro- / V-[2-(2-chloro-4-methyl- phenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1 .100), 6-chloro- / V-[2-(2-chloro-

[0411] 4-methyl-phenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-

[0412] 4-carboxamide (K.1 .101), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-A / -[2-(3,4-dimethylphenyl)-

[0413] 2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.102), 6-chloro-3-(3-chloro-2-fluoro- phenoxy)- / V-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1 .103), A / -[2-(2-bromo-4-methyl-phenyl)-2,2-difluoro-ethyl]-6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-

[0414] 5-methyl-pyridazine-4-carboxamide (K.1 .104), 2-[cyano-(2,6-difluoro-4-pyridyl)amino]-5-methyl-

[0415] A / -spiro[3.4]octan-3-yl-thiazole-4-carboxamide, 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-

[0416] A / -(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, 2-[(2,6-difluoro-4-pyridyl)-

[0417] (2-methoxyacetyl)amino]- / V-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, 2-[cyano- (2,6-difluoro-4-pyridyl)amino]- / V-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, / V-[1-[[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]-5-[(Z)- / V-isopropoxy-C-methyl-carbonimidoyl]- 2,6-dioxo-pyrimidin-1-yl]methyl]-2-methyl-propyl]-2-methyl-propanamide, A / -[1-[[3-[2-(5-fluoro-

[0418] 2-methoxy-phenyl)-2-hydroxy-ethyl]-5-[(Z)-A / -isopropoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-

[0419] 1-yl]methyl]-2-methyl-propyl]-2,2-dimethyl-propanamide, / V-[2-[3-[2-(5-fluoro-2-methoxy-phenyl)-

[0420] 2-hydroxy-ethyl]-5-[(Z)- / V-isopropoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]-1-methyl- ethyl]-2-methyl-propanamide, A / -[2-[3-[2-hydroxy-2-(2-methoxyphenyl)ethyl]-5-[(Z)-A / -isopropoxy- C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propanamide, A / -[2-[3-[2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxy-phenyl)ethyl]-5-[(Z)-A / -isopropoxy-C-methyl- carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propanamide, rac-3-[3-(3-chloro- 79

[0421] 2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-

[0422] 4 / 7-1 ,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-4 / 7-1 ,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-4 / 7-1 ,2,4-oxadiazine,

[0423] 2-(4-fluorophenoxy)-1-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]ethanone, 2-[(6-fluoro-

[0424] 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-oxadiazol-3-yl]phenyl]ethenone, ethyl 1 -[[4-[[2-(trifluoromethyl)-

[0425] 1 .3-dioxolan-2-yl]methoxy]phenyl]methyl]-1 / 7-pyrazole-4-carboxylate, ethyl 1-[[4-[[(1Z)-2-ethoxy-

[0426] 3.3.3-trifluoro- 1 -propen-1 -yl]oxy]phenyl]methyl]-1 / 7-pyrazole-4-carboxylate.

[0427] 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.

[0428] The active substances referred to as component 2) or 3) herein, 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-141 317; EP-152 031 ; EP-226 917; EP-243 970;

[0429] EP-256 503; EP-428 941 ; EP-532 022; EP-1 028 125; EP-1 035 122; EP-1 201 648; EP-1 122 244,

[0430] JP2002316902; DE19650197; DE10021412; DE102005009458; US 3,296,272; US 3,325,503

[0431] WO 98 / 46608; WO 99 / 14187; WO 99 / 24413; WO 99 / 27783; WO 00 / 29404; WO 00 / 46148

[0432] WO 00 / 65913; WO 01 / 54501 ; WO 01 / 56358; WO 02 / 22583; WO 02 / 40431 ; WO 03 / 10149

[0433] WO 03 / 11853; WO 03 / 14103; WO 03 / 16286; WO 03 / 53145; WO 03 / 61388; WO 03 / 66609

[0434] WO 03 / 74491 ; WO 04 / 49804; WO 04 / 83193; WO 05 / 120234; WO 05 / 123689; WO 05 / 123690

[0435] WO 05 / 63721 ; WO 05 / 87772; WO 05 / 87773; WO 06 / 15866; WO 06 / 87325; WO 06 / 87343

[0436] WO 07 / 82098; WO 07 / 90624, WO 10 / 139271 , WO 11 / 028657, WO 12 / 168188, WO 07 / 006670, WO

[0437] 11 / 77514; WO 13 / 047749, WO 10 / 069882, WO 13 / 047441 , WO 03 / 16303, WO 09 / 90181 ,

[0438] 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 ,

[0439] WO 08 / 013622, WO 15 / 65922, WO 94 / 01546, EP 2865265, WO 07 / 129454, WO 12 / 165511 ,

[0440] WO 11 / 081174, WO 13 / 47441 , WO 16 / 156241 , WO 16 / 162265, WO 23 / 99460, WO 21 / 244950,

[0441] WO 21 / 244951 , WO 22 / 130188, WO 22 / 243810, WO 21 / 255070, WO 21 / 176057, WO 21 / 153754,

[0442] JP2023064110, JP2022153603, JP2022046550, JP2022031355, WO 22 / 249074, WO 23 / 046861 ,

[0443] WO 18 / 177894, WO 20 / 212513, WO 20 / 097012, US 2023 / 0069915. Some compounds are identified by their CAS Registry Number.

[0444] Suitable mixing partners for the compounds of the invention also include biopesticides. 80

[0445] 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, microbial and biochemical pesticides:

[0446] (1) Microbial pesticides consist of bacteria, fungi or viruses (and often include the metabolites that bacteria and fungi produce). Entomopathogenic nematodes are also classified as microbial pesticides, even though they are multi-cellular.

[0447] (2) Biochemical pesticides are naturally occurring substances or or structurally-similar and functionally 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.

[0448] The following list of biopesticides, in conjunction with which the compounds of the invention can be used, illustrates the possible combinations:

[0449] L) Biopesticides

[0450] L1) Microbial pesticides with fungicidal, bactericidal, viricidal and / or plant defense activator 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 rose urn, Lysobacter antibioticus, L. enzymogenes, Metschnikowia fructicola, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor albus, Paenibacillus alvei, Paenibacillus epiphyticus, 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);

[0451] L2) Biochemical pesticides with fungicidal, bactericidal, viricidal and / or plant defense activator 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);

[0452] L3) Microbial pesticides with insecticidal, acaricidal, molluscidal and / or nematicidal activity: Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. 81 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 capsid nucleopolyhedrovirus (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;

[0453] L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal, pheromone and / or nematicidal 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-tetradecen-1-ol, extract of Chenopodium ambrosiodes, Neem oil, Quillay extract;

[0454] L5) Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting 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. I. bv. tri foil! , R. I. bv. viciae, R. tropic!, Sinorhizobium meliloti.

[0455] 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 growth regulator, plant growth promoting and / or yield enhancing activity. The biopesticides from group L5) may also have fungicidal, bactericidal, viricidal, plant defense activator, insecticidal, acaricidal, molluscidal, pheromone and / or nematicidal activity.

[0456] 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 details see 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 82 prior to 1980 (BR 11005; e.g. GELFIX® Gramineas from BASF Agricultural Specialties Ltd., Brazil), A. brasilense strains Ab-V5 and Ab-V6 (e.g. in AzoMax from Novozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazil or Simbiose-Maiz® 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 (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. vele-zensis MBI600 isolated from faba 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 1 BE; ATCC BAA-390; CA 2471555 A1 ; e.g. QuickRoots™ from TJ Technologies, Watertown, SD, USA); B. firmus CNCM 1-1582, a variant of parental strain EIP-N1 (CNCM 1-1556) 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 as BU 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 B 30087; 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, Munsingen, Germany), B. t. ssp. kurstaki ABTS-351 identical to 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 strain NB-125, a wild type strain isolated in 1982 from a dead pupa of the beetle Tenebrio molitor (DSM 5480; EP 585 215 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 83 of the tortoise beetle Conchyloctenia punctata (NRRL 50757; e.g. BroadBand® from BASF Agricultural Specialities (Pty) Ltd., South Africa), Bradyrhizobium elkanii strains SEMIA 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 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 SEMIA 5080 obtained under lab condtions by Embrapa-Cerrados in Brazil and used in commercial inoculants 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 isolated from oilseed rape (WO 1996 / 021358; DSM 9660; e.g. Contans® WG, Intercept® WG from Bayer CropScience AG, Germany), harpin (alpha-beta) protein (Science 257, 85-88, 1992; e.g. Messenger™ or HARP-N Tek from Plant Health Care pic, 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 from AgBiTech 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. (ATCC 20874; Biocontrol Science Technol. 22(7), 747-761 , 2012; e.g. PFR-97™ or PreFeRal® from Certis 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 (AGAL 89 / 030550; WQ1991 / 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 including Germany: 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-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 84 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® from Novozymes 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 BASF Agricultural Specialities Limited, UK), Streptomyces microflavus NRRL B-50550 (WO 2014 / 124369; Bayer CropScience, Germany), Trichoderma asperelloides JM41 R 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™ from Advanced Biological Marketing Inc., Van Wert, OH, USA).

[0457] According to the invention, the solid material (dry matter) of the biopesticides (with the ex-ception 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).

[0458] In accordance with the invention, the weight ratios and percentages used herein for a biological extract e.g. Quillay extract are based on the total weight of the dry content (solid material) of the respective extract(s).

[0459] 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 of the respective microorganism to calculate the total weight of the respective active component with the 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. Steinernema feltiae.

[0460] 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), the application rates regularly range from 1x105to 1x1012(or more), preferably from 1x108to 1x1011, more preferably from 5x108to 1x101° individuals (e.g. in the form of eggs, juvenile or any other live stages, preferably in an infetive juvenile stage) per ha.

[0461] 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. 85

[0462] 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 100 kg of seed.

[0463] Formulations

[0464] The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of the invention or a mixture thereof.

[0465] An agrochemical composition comprises a pesticidally effective amount of a compound of the invention or a mixture thereof.

[0466] The compounds of the invention or the mixtures thereof can be converted into customary types of agrochemical compositions, e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (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 compositions types are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.

[0467] 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.

[0468] 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.

[0469] Suitable solvents and liquid carriers are water and organic solvents, e.g. mineral oil fractions of medium 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; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

[0470] 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; 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. 86

[0471] Suitable surfactants are surface-active compounds, e.g. anionic, cationic, nonionic and am-photeric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, 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.).

[0472] 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 of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.

[0473] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds e.g. alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or 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-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

[0474] 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 amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-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, or polyethyleneamines.

[0475] 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 auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5. 87

[0476] Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

[0477] Suitable bactericides are bronopol and isothiazolinone derivatives e.g. alkylisothiazolinones and benzisothiazolinones.

[0478] Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea, and glycerin.

[0479] Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.

[0480] 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, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo-, and phthalocyanine colorants).

[0481] Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

[0482] Examples for composition types and their preparation are: i) Water-soluble concentrates (SL, LS)

[0483] 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)

[0484] 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)

[0485] 15-70 wt% of a compound I according to the invention and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate 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)

[0486] 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-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into up to 100 wt% water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion. v) Suspensions (SC, OD, FS)

[0487] In an agitated ball mill, 20-60 wt% of a compound I according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance 88 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. vi) Water-dispersible granules and water-soluble granules (WG, SG)

[0488] 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 of the active substance. vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

[0489] 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. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substance. viii) Gel (GW, GF)

[0490] 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 active substance. Dilution with water gives a stable suspension of the active substance. ix) Microemulsion (ME)

[0491] 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. alcohol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion. x) Microcapsules (CS)

[0492] 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 aqueous solution 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 for-ation of a polyurea microcapsule. The monomers amount to 1-10 wt%. The wt% relate to the total CS composition. xi) Dustable powders (DP, DS)

[0493] 1-10 wt% of a compound I according to the invention are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin. xii) Granules (GR, FG)

[0494] 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) 89

[0495] 1-50 wt% of a compound I according to the invention are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.

[0496] The compositions 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.

[0497] The agrochemical compositions generally comprise between 0.01 and 95%, preferably be-tween 0.1 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).

[0498] 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 active substances 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.

[0499] The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agro-chemical composition 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.

[0500] 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.

[0501] 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, may be mixed by the user in a spray tank and further auxiliaries and additives may be added.

[0502] 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) or consecutively.

[0503] Application methods

[0504] 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 90 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, in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of a compound of the invention.

[0505] The compounds of the invention are also suitable for use in combating 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 the crops, plants, plant propagation materials, e.g. seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesticidally effective amount of a compound of the invention.

[0506] 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.

[0507] 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 is immediately 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.

[0508] 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.

[0509] Suitable application methods include i.a. soil treatment, seed treatment, in furrow application, and foliar 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 furrow with seeds, applying the pesticidally active compound to the furrow, and closing the furrow. Foliar application 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 of pheromones and semiochemicals, e.g. http: / / www.pherobase.com.

[0510] 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, breeding 91 ground, plant, seed, soil, area, material, or environment in which a pest is growing or may grow, of the animal pest or plant).

[0511] 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.

[0512] The term "crop" refers to both, growing and harvested crops.

[0513] 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; leguminous plants, 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 potatoes sugar 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.

[0514] The term "cultivated plants" is to be understood as including plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.

[0515] 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 like CRISPR / Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.

[0516] 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 also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants. The process of plant 92 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 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.

[0517] 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 of mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield®.

[0518] Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and HPPD inhibitors, like isoxaflutole and mesotrione.

[0519] 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 to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.

[0520] 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 , MZHGOJG, HCEM485, VCO-01981-5, 676, 678, 680, 33121 , 4114, 59122, 98140, Bt10, Bt176, CBH-351 , DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.

[0521] 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, SYHT0H2, W62, W98, FG72 and CV127.

[0522] Transgenic cotton events comprising herbicide tolerance genes are e.g., but not excluding others, 19- 51 a, 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.

[0523] Transgenic canola events comprising herbicide tolerance genes are e.g., but not excluding others, MON88302, HCR-1 , HCN10, HCN28, HCN92, MS1 , MS8, PHYU, PHY23, PHY35, PHY36, RF1 , RF2 and RF3. 93

[0524] Insect resistance has mainly been created by transferring bacterial genes for insecticidal pro-teins to plants. Transgenes which have most frequently been used are toxin genes of Bacillus spec, and synthetic variants thereof, like cry1A, crylAb, cry1Ab-Ac, crylAc, cry1A.1 O5, cry1 F, cry1 Fa2, 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 pinll. A further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate in-sect genes. An example for such a transgene is dvsnf7.

[0525] 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.

[0526] Transgenic soybean events comprising genes for insecticidal proteins are e.g., but not excluding others, MON87701 , MON87751 and DAS-81419.

[0527] Transgenic cotton events comprising genes for insecticidal proteins are e.g., but not excluding others, SGK321 , MON531 , MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601 , Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210- 23, GHB119 and SGK321.

[0528] Increased yield has been created by increasing ear biomass using the transgene athb17, be-ing present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.

[0529] Cultivated plants comprising a modified oil content have been created by using the transgenes: gm- fad2-1 , Pj.D6D, Nc.Fad3, fad2-1 A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.

[0530] Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb-4, comprised by soybean event IND-00410-5.

[0531] 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 particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbicide tolerance and tolerance to abiotic conditions. 94

[0532] 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).

[0533] Further information on specific events and methods to detect them can be found for canola events MS1 , MS8, RF3, GT73, MON88302, KK179 in W001 / 031042, W001 / 041558, W001 / 041558, W002 / 036831 , WO11 / 153186, W013 / 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, W002 / 100163, W002 / 100163, W003 / 013224, WO04 / 072235, WO04 / 039986, WO05 / 103266, WO05 / 103266, WO06 / 128573, W007 / 017186, WO08 / 122406, WG08 / 151780, WO12 / 134808, WO13 / 112527, for corn events GA21 , MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, 4114, MON87427, DAS40278, MON87411 , 33121 , MON87403, MON87419 in WG98 / 044140, US02 / 102582, US03 / 126634, WO04 / 099447, WG04 / 011601 , WO05 / 103301 , WG05 / 061720, WG05 / 059103, WO06 / 098952, WO06 / 039376, US2007 / 292854, WO07 / 142840, WO07 / 140256, WG08 / 112019, WO09 / 103049, WO09 / 111263, WO10 / 077816, W011 / 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 , W017 / 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, W008 / 002872, WO09 / 064652, W009 / 102873, W010 / 080829, W010 / 037016, WO11 / 066384, WO11 / 034704, WO12 / 051199, WO12 / 082548, WO13 / 016527, WO13 / 016516, WO14 / 201235.

[0534] 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 or heat tolerance as well as changed amino acid or fatty acid spectrum or content.

[0535] 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 the insecticidal trait is not effective, so that a complementary insecticidal activity can advantageously be used.

[0536] 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 forthe multiplication 95 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.

[0537] The term “seed” embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.

[0538] 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 various compounds / compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions e.g. desired pesticidal effect and duration, weather, target species, locus, mode of application.

[0539] 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 from 0.001 to 20 g per 100 m2.

[0540] 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 hec-tare, 30 to 40 g per hectare, or 40 to 50 g per hectare.

[0541] 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 also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the 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 and nematodes.

[0542] 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. 96

[0543] 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.

[0544] 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 I 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, 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.

[0545] In addition, the active compound may also be used for the treatment of seeds from plants, which have been modified by mutagenesis or genetic engineering, and which e.g. tolerate the action of herbicides or fungicides or insecticides.

[0546] 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 is carried 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.

[0547] 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 to 40% by weight.

[0548] 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.

[0549] Especially preferred FS formulations of the compounds of the invention for seed treatment usually comprise 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% by weight, 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. 97 a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler / veh icle up to 100% by weight.

[0550] In the treatment of seed, the application rates of the compounds of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably 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.

[0551] 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 invention orthe 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.

[0552] 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.

[0553] As used herein “an effective and non-phytotoxic amount” means that the compound is used in a quantity 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.

[0554] "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 / or increased content of valuable ingredients), quality (e.g. improved content or composition of certain 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).

[0555] The above identified indicators for the health condition of a plant may be interdependent and may result from each other. Each indicator is defined in the art and can be determined by methods known to a skilled person.

[0556] 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 or surface applied). Furthermore, drenching and rodding methods can be used. 98

[0557] As used herein, the term “non-crop insect pest” refers to pests, which are particularly relevant for noncrop targets, e.g. ants, termites, wasps, flies, ticks, mosquitoes, bed bugs, crickets, or cockroaches.

[0558] The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). The bait employed in the composition 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 of animal 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).

[0559] 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.

[0560] 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 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.

[0561] The oil spray formulations differ from the aerosol recipes in that no propellants are used.

[0562] For use in spray compositions, the content of active ingredient is from 0.001 to 80 wt%, preferably from 0.01 to 50 wt% and most preferably from 0.01 to 15 wt%.

[0563] 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.

[0564] Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, 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 comprise a mixture including the insecticide, optionally a repellent and at least one binder.

[0565] 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 99 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 from doing harm to crops or human beings (e.g. when the pests invade into houses and public facilities or nest in yards, orchards or parks).

[0566] 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.

[0567] Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 wt%, preferably from 0.1 to 45 wt%, and more preferably from 1 to 25 wt% of at least one repellent and / or insecticide.

[0568] Digital application

[0569] The compounds of the invention and the compositions containing them may be applied in combination 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 of pest pressure and smart application of crop protection products, secure environ-mental protection, 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.

[0570] Commercially available systems which include agronomic models are e.g. FieldScripts™ from The Climate Corporation, Xarvio™ from BASF, AGLogic™ from John Deere, etc.

[0571] 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 / or unwanted vegetation, weather information, information on the location of the area and directly derivable information thereof, information on pest pressure, information on beneficial organisms, and I or historic information of any of the aforementioned.

[0572] 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 sources typically includes proximate-detection systems like soil-borne sensors and remote sensing as may 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 recommendations and generate control signals. 100

[0573] Typical technologies that are used in smart agricultural technologies include self-steering robots (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.

[0574] Precision agriculture such as precision farming is characterized by spatially and / or temporally resolved, targeted application of active ingredients like pesticides, plant-growth-regulators, fertilizers, and / orwater 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 a agronomic site. Precision farming typically includes the use of geo-positioning technologies like GPS for gaining information on the location and boundaries 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.

[0575] Precision farming may typically include the application of smart spraying equipment, e.g. spot spraying, 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 to apply 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 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.

[0576] Pests

[0577] The 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, 101

[0578] 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, Caloptilis theivora, 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., Colias eurytheme, 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; Diatraea grandiosella, Diatraea saccharalis, Diphthera festiva, Earias spp. e.g. E. insulana, E. vittella; Ecdytolopha aurantianu, Egira (=Xylomyges) curialis, Elasmopalpus lignosellus, Eldana saccharina, Endopiza viteana, Ennomos 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, Euxoa spp., Evetria bouliana, Faronta albilinea, Feltia spp. e.g. F. subterranean; Galleria mellonella, Gracillaria spp., Grapholita spp. e.g. G. funebrana,

[0579] G. molesta, G. inopinata; Halysidota spp., Harrisina americana, Hedylepta spp., Helicoverpa spp. e.g.

[0580] H. armigera (=Heliothis armigera), H. 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, Lambdina fiscellaria 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, Lyonetia prunifoliella, 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, 102

[0581] 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-dia interpunctella, 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, Thaumetopoea pityocampa, 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; 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, Anomala rufocuprea, 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, Cetonia aurata, 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, Faustinas cubae, Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Hylamorpha elegans, Hylobius abietis, Hylotrupes bajulus, Hypera spp., e.g. H. brunneipennis, H. postica; Hypomeces squamosus, Hypothenemus spp., Ips typographus, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lerna spp. e.g. L. bilineata, L. melanopus; Leptinotarsa spp. e.g. L. decemlineata; Leptispa pygmaea, Limonius californi-cus, Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp., Lyctus spp. e.g. L. bruneus; 103

[0582] 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, Oryzaphagus oryzae, 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, Prostephanus truncates, 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. 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, Chrysops discalis, 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, Dasineura oxycoccana, 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, Leptoconops torrens, 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, Prosimulium mixtum, 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; 104 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 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,

[0583] 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.

[0584] 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, Doralis spp., 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, Lipaphis erysimi, 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 105 costalis, Mo-nelliopsis pecanis, Myzocallis coryli, 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 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, Piezodorus spp. e.g. P. guildinii; Pinnaspis aspidistrae, Pianococcus spp. e.g. P. citri, P. ficus; Prosapia bicincta, 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., Rhopalomyzus ascalonicus, 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, Stephanitis pyrioides, Stephanitis takeyai, Tenalaphara malayensis, Tetraleurodes perseae, Therioaphis maculate, 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 septemfasciata, Oedaleus senegalensis, Scapteriscus spp., 106

[0585] 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 and Polyphagotarsonemus latus, Stenotarsonemus spp. Steneotarsonemus spinki; Family Tenuipalpidae 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 Oligonychus spp. e.g. O. pratensis, O. perseae, Vasates lycopersici; Raoiella indica, Family Carpoglyphidae including 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 including Latrodectus mactans, Eratigena agrestis, Cheiracanthium sp, Lycosa sp Achaearanea tepidariorum 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 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 107 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..

[0586] 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 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, Dracunculus medinensis, 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 108 saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.

[0587] The compounds of the invention are particularly suitable for efficiently combating insects from the suborder of Auchenorrhyncha, e.g. Amrasca biguttula, Empoasca spp., Nephotettix virescens, Sogatella furcifera, Mahanarva spp., Laodelphax striatellus, Nilapar-vata lugens, Diaphorina citri, Lycorma delicatula, Pentastiridus leporinus;

[0588] 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;

[0589] True bugs, e.g. Lygus spp., Stink bugs such as Euschistus spp., Halyomorpha halys, Nezara viridula, Piezodorus guildinii, Dichelops furcatus;

[0590] Thrips, e.g. Frankliniella spp., Thrips spp., Dichromothrips corbettii;

[0591] Aphids, e.g. Acyrthosiphon pisum, Aphis spp., Myzus persicae, Rhopalosiphum spp., Schi-zaphis graminum, Megoura viciae;

[0592] Whiteflies, e.g. Trialeurodes vaporariorum, Bemisia spp.;

[0593] Coleoptera, e.g. Phyllotreta spp., Melanotus spp., Meligethes aeneus, Leptinotarsa decimlineata, Ceutorhynchus spp., Diabrotica spp., Anthonomus grandis, Atomaria linearia, Agriotes spp., Epilachna spp.;

[0594] Flies, e.g. Delia spp., Ceratitis capitate, Bactrocera spp., Liriomyza spp.;

[0595] Coccoidea, e.g. Aonidiella aurantia, Ferrisia virgate;

[0596] Anthropods of class Arachnida (Mites), e.g. Penthaleus major, Tetranychus spp.;

[0597] Nematodes, e.g. Heterodera glycines, Meloidogyne sp., Pratylenchus spp., Caenorhabditis elegans.

[0598] Animal health

[0599] The 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 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.

[0600] The invention also relates to the non-therapeutic use of compounds of the invention for treating or 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.

[0601] The compounds of the invention are further suitable for use in combating or controlling parasites in and on animals. Furthermore, the invention relates to a method of combating or con-trolling parasites in and 109 on animals, which comprises contacting the parasites with a parasitically effective amount of a compound of the invention.

[0602] 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 of combating or controlling parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the invention.

[0603] 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 of the invention can be applied to any and all developmental stages.

[0604] The compounds of the invention can be applied as such or in form of compositions comprising the compounds of the invention.

[0605] 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 or Semduramicin, or with other mixing partners as defined above, or in form of compositions comprising said mixtures.

[0606] 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 or non-systemically effective.

[0607] 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.

[0608] As used herein, the term "contacting" includes both direct contact (applying the compounds / compositions directly on the parasite, including the application directly on the animal or excluding 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 through application to its locus is an example of a non-therapeutic use of the compounds of the invention.

[0609] 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.

[0610] As used herein, the term “parasites” includes endo- and ectoparasites. In some embodiments of the 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. 110

[0611] The compounds of the invention are especially useful for combating parasites of the following orders 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, Fannia canicularis, 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 parasitic mites (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., Cytodites spp., 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.; 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., Globocephalus spp., 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 111 canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi; Camallanida, e.g. Dracunculus medinensis (guinea worm); Spirurida, e.g. Thelazia spp., Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp. 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, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp., and Nanocyetes 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..

[0612] The term “animal” includes warm-blooded animals (including humans) and fish. Preferred are mammals, 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.

[0613] Generally, "parasiticidally 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 parasiticidally effective amount can vary for the various compounds / compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions e.g. desired parasiticidal effect and duration, target species, mode of application.

[0614] 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.

[0615] 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 should provide the animal with 0.01 mg / kg to 100 mg / kg of animal body weight per day of the compounds I, preferably with 0.5 mg / kg to 100 mg / kg of animal body weight per day.

[0616] 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, the compounds I may be formulated into an implant for subcutaneous administration. In addition the compounds I may be 112 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.

[0617] 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.

[0618] Suitable preparations are:

[0619] - Solutions e.g. oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;

[0620] - Emulsions and suspensions for oral or dermal administration; semi-solid preparations;

[0621] - Formulations in which the active compound is processed in an ointment base or in an oil-in-water or water-in-oil emulsion base;

[0622] - Solid preparations e.g. powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.

[0623] 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 are filtered 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.

[0624] 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 what is described above for injection solutions, sterile procedures not being necessary.

[0625] 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 with sufficient thickener that a clear material having an ointment-like consistency results. Suitable thickeners are known in the art.

[0626] 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 solvent mixtures. If appropriate, other auxiliaries e.g. colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added. Suitable such auxiliaries are known in the art. 113

[0627] 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 either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase 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.

[0628] Suspensions can be administered orally or topically / dermally. They are prepared by suspending the 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.

[0629] Semi-solid preparations can be administered orally or topically / dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.

[0630] 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.

[0631] The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compound of the invention.

[0632] 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.

[0633] Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90% by weight, preferably of 1 to 50% by weight.

[0634] 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.

[0635] 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. 114

[0636] 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.

[0637] 115

[0638] Examples

[0639] Method A: HPLC-MS: SHIMADZU LCMS-2020 ESI; Column: Diamonsil plus 5 pm 30*4.6mm; Mobile Phase: A: water + 0.05% TFA; B: ACN; Temperature: 40°C; Flow: 2.0 mL / min; MS: ESI positive; Mass range (m / z): 100-1000.

[0640] Method B: HPLC-MS: Column: ACQUITY UPLC BEH C18 1.7pm, (2.1X50)mm, Mobile Phase A: 0.1 % TFA in Water, B: 100% ACN, Gradient (T%B): 0.0 / 03, 1.0 / 03, 7.0 / 95, 7.5 / 95, 9.0 / 03, 10 / 03, Flow Rate: 0.5ml / min, Column Temp: 40°C, Sample Diluent: ACN+WATER; MS: ESI positive Mass range (m / z): 100-1800

[0641] Method C: HPLC-MS: Shimadzu Nexera UHPLC + Shimadzu LCMS 20-20, ESI Column: Phenomenex Kinetex 1 ,7pm XB-C18 100A, 50 x 2,1 mm; Mobile Phase: A: water + 0,1 % TFA; B:ACN, Temperature: 60°C, Gradient:5% B to 100% B in 1 ,50min; 100% B 0,25min, Flow: 0,8ml / min to 1 ,0ml / min in 1 ,51 min, MS method: ESI positive, Mass range (m / z): 100-700

[0642] Method D: Column: X-Bridge C18, 5u (4.6mmX100mm) Mobile Phase A: 10 mM Ammonium Bicarbonate in Water, B: 100% ACN, Gradient (T%B): 0 / 10, 8 / 95, 11 / 95, 13 / 10,15 / 10, Flow Rate: 1.0 ml / min Column Temp: 40°C, Sample Diluent: ACN+WATER

[0643] Method E: Acquity UPLC BEH C18, 1.7pm (50mmX2.1 mm), Mobile Phase A: 0.1 % Formic Acid in Water, B: 0.1 % Formic Acid in ACN, Gradient (T%B): 0 / 3, 1.0 / 3, 7.0 / 95, 7.5 / 95, 9.0 / 3, 10.0 / 3, Flow Rate: 0.5ml / min, Column Temp: 40°C Mass range (m / z): 100-700

[0644] Synthesis of compound 1-1

[0645] Step 1. (5-(tributylstannyl)pyrazin-2-yl)methanol 116

[0646] A solution of (5-bromopyrazin-2-yl)methanol (5 g, 34.6 mmol), Tetrakis(triphenylphosphine)palladium (2 g, 1 .73 mmol) and Hexabutylditin (100 g, 173 mmol) in dioxane (10 mL) under nitrogen was stirred at 110°C for 24 h. The reaction was concentrated with silica gel and purified by chromatography on silica gel (petrol ether / ethyl acetate = 5 / 1) to afford the title compound (2 g, 14% yield).

[0647] LC-MS (ES) m / z = 401 .1 (M+H)+

[0648] Step 2. (5-(1 -(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)methanol

[0649] A solution of (5-(tributylstannyl)pyrazin-2-yl)methanol (1.92 g, 4.80 mmol), 3-bromo-1-[4- (trifluoromethoxy)phenyl]-1 ,2,4-triazole (1.0 g, 3.2 mmol), Pd(PPti3)4 (0.37 g, 0.32 mmol) and Copper(l) iodide (0.06 g, 0.32 mmol) in dioxane (20 mL) under nitrogen was stirred at 110°C for 4 h. The mixture was concentrated. The residue was purified by column chromatography on silica gel (petrol ether / ethyl acetate = 2 / 1) to afford the title compound (0.75 g, 66% yield).

[0650] LC-MS (ES) m / z = 338.2 (M+H)+

[0651] Step 3. 5-( 1 -(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazine-2-carbaldehyde

[0652] A solution of (5-(1-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)methanol (730 mg, 2.16 mmol), MnC>2 (940.9 mg, 10.82 mmol) in CHCh (10 mL) was stirred at 70°C for 24 h. The mixture was filtered, and the filtrate was concentrated to afford the title compound (700 mg, 87% yield) as colorless solid.

[0653] LC-MS (ES) m / z = 336.2 (M+H)+.

[0654] 1H NMR (300 MHz, CDCb) 6 10.23 (s, 1 H), 9.63 (s, 1 H), 9.30 (s, 1 H), 8.73 (s, 1 H), 7.88 (d, J = 6.6 Hz, 2H), 7.44 (d, J = 6.6 Hz, 2H).

[0655] Step 4. (E)-2-(2-nitrovinyl)-5-(1 -(4-(trifluoromethoxy)phenyl)-1H-1 ,2,4-triazol-3-yl)pyrazine

[0656] A solution of 5-(1-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazine-2-carbaldehyde (700 mg, 2.09 mmol), TEA (211 mg, 2.09 mmol) in CH3NO2 (8 mL) was stirred at rt for 1 h. The mixture was concentrated. To the residue was added AC2O (2132 mg, 20.88 mmol), pyridine (1652 mg, 20.88 mmol). The mixture was stirred at rt for 2 h. The mixture was triturated with water (50mL) and filtered. The filter cake was triturated with petrol ether / ethyl acetate = 10:1 to afford the title compound (600 mg, 53% yield).

[0657] LC-MS (ES) m / z = 379.2 (M+H)+.

[0658] Step 5. 2-(2-Nitroethyl)-5-(1 -(4-(trifluoromethoxy)phenyl)-1H-1 ,2,4-triazol-3-yl)pyrazine

[0659] To a solution of (E)-2-(2-nitrovinyl)-5-(1-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazine (800 mg, 2.11 mmol) in MeOH (5 mL) was added NaBH4 (160 mg, 4.23 mmol). The reaction mixture was stirred at rt for 10 mins. The mixture was concentrated. The residue was purified by column chromatography on silica gel (petrol ether / ethyl acetate = 100 / 0 to 0 / 100) to afford the title compound (200 mg, 25% yield).

[0660] LC-MS (ES) m / z = 381 .1 (M+H)+. 117

[0661] Step 6. 2-(5-(1-(4-(Trifluoromethoxy)phenyl)-1H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)ethan-1-amine

[0662] A mixture of 2-(2-Nitroethyl)-5-(1-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazine (200 mg, 0.53 mmol) and Pd / C (20 mg, 10%wt) in MeOH (3 mL) was stirred under an atmosphere of H2 at 30°C for 16 h. The mixture was filtered, and the filtrate was concentrated to afford the title compound (182 mg, 99% yield).

[0663] LC-MS (ES) m / z = 350.8 (M+H)+.

[0664] Step 7. / V-(2-isopropyl-5-methylphenyl)-1 -({[2-(5-{1 -[4-(trifluoromethoxy)phenyl]-1 ,2,4-triazol-3- yl)pyrazin-2-yl)ethyl]carbamoyl}amino)methanethioamide

[0665] A mixture of 2-(5-(1 -(4-(T rifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)ethan-1 -amine (300 mg, 0.86 mmol), phenyl N-(phenylcarbamothioyl)carbamate (422 mg, 1.28 mmol) and diisopropyl ethylamine (332 mg, 2.57 mmol) in ACN (5 mL) was stirred at 30°C for 2 h. The mixture was concentrated. The residue was purified by column chromatography on silica gel (CH2Cl2 / MeOH = 100 / 0 to 90 / 10) to afford the title compound (160 mg, 32% yield).

[0666] LC-MS (ES) m / z = 585.2 (M+H)+.

[0667] Step 8. (Z)-1 -(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)-3-(2-(5-(1 -(4-

[0668] (trifluoromethoxy)phenyl)-1H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)ethyl)urea (compound 1-1 )

[0669] A mixture of N-(2-isopropyl-5-methylphenyl)-1-({[2-(5-{1-[4-(trifluoromethoxy)phenyl]-1 ,2,4-triazol-3- yl}pyrazin-2-yl)ethyl]carbamoyl}amino)methanethioamide (150 mg, 0.26 mmol), ethyl 2-bromoacetate (86 mg, 0.51 mmol) and NaOAc (42 mg, 0.51 mmol) in EtOH (2 mL) was stirred at 50°C under N2 for 16 h. The mixture was concentrated. The residue was purified by prep-HPLC to afford the title compound (64 mg, 40% yield) as a white solid. LC-MS (ES) m / z = 625.1 (M+H)+.1H NMR (400 MHz, DMSO-cfe) 6 9.51 (s, 1 H), 9.21 (d, J = 1.2 Hz, 1 H), 8.59 (d, J = 0.8 Hz, 1 H), 8.10 (d, J = 8.8 Hz, 2H), 7.65-7.63 (m, 3H), 7.33 (d, J = 8.0 Hz, 1 H), 7.21 (d, J = 8.0 Hz, 1 H), 6.97 (s, 1 H), 4.12-3.96 (m, 2H), 3.46-3.43 (m, 2H), 2.99 (t, J = 6.8 Hz, 2H), 2.62-2.55 (m, 1 H), 2.27 (s, 3H), 1.10-1.04 (m, 6H).

[0670] 118

[0671] Synthesis of compounds I-2, 1-3, 1-4:

[0672] Step 1. 1-(5-(Tributylstannyl)pyrazin-2-yl)ethan-1-one

[0673] To a mixture of 1-(5-chloropyrazin-2-yl)ethanone (1 g, 6.4 mmol) and Pd(PPhs)4 (0.74 g, 0.6 mmol) was added Sn2Bue (9.3 g, 16 mmol). The reaction mixture was stirred at 110°C for 60 h. The mixture was purified by column chromatography on silica gel (petrol ether / ethyl acetate = 20 / 1) to afford the title compound (0.45 g, 17% yield).

[0674] LC-MS (ES) m / z = 412.2 (M+H)+.

[0675] Step 2. 1 -(5-( 1 -(4-(T rifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)ethan-1 -one

[0676] To a solution of 3-bromo-1-[4-(trifluoromethoxy)phenyl]-1 ,2,4-triazole (300 mg, 1 .0 mmol) in NMP (3 mL) was added 1-(5-(Tributylstannyl)pyrazin-2-yl)ethan-1-one (420 mg, 1.0 mmol), CU2O (70 mg, 0.5 mmol), DPPP (60 mg, 0.1 mmol) and Palladium diacetate (22 mg, 0.1 mmol) at room temperature. The mixture was stirred at 120°C under N2 for 3 h. The reaction was quenched by addition of water (20 mL). The mixture was extracted with EtOAc (20 mL * 2). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (petrol ether / ethyl acetate = 3 / 1) to afford the title compound (160 mg, 47% yield.

[0677] LC-MS (ES) m / z = 350.2 (M+H)+. 119

[0678] Step 3. Tert-Butyl 2-(1-(5-(1-(4-(trifluoromethoxy)phenyl)-1H-1 ,2,4-triazol-3-yl)pyrazin-2- yl)ethyl)hydrazine-1 -carboxylate 1-(5-(1-(4-(Trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)ethan-1-one (1.0 g, 2.9 mmol), (tert-butoxy)carbohydrazide (0.4 g, 3.1 mmol) and AcOH (0.5 g, 8.6 mmol) were added successively in EtOH (10 mL). The reaction mixture was stirred at 80°C for 4 h and then NaBHsCN (1.110 g, 17.2 mmol) was added. The reaction mixture was stirred at 80°C for 16 h. The reaction was quenched by the addition of water (10 mL). The mixture was extracted with EtOAc (20 mL * 2). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered, and concentrated to afford the title compound (1 .2 g, 89% yield).

[0679] LC-MS (ES) m / z = 466.0 (M+H)+.

[0680] Step 4. 2-(1 -Hydrazineylethyl)-5-(1 -(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazine

[0681] A mixture of tert-butyl 2-(1-(5-(1-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2- yl)ethyl)hydrazine-1 -carboxylate (1 .2 g, 2.6 mmol) in CH2CI2 / TFA = 3 / 1 (12 mL) was stirred at rt for 5 h. The solvent was evaporated, and the mixture was directly used to the next step without purification. LC-MS (ES) m / z = 365.8 (M+H)+.

[0682] Step 5. W-((2-lsopropyl-5-methylphenyl)carbamothioyl)-2-(1 -(5-(1 -(4-(trifluoromethoxy)phenyl)- 1H-1 ,2, 4-triazol-3-y I )pyrazin-2-yl )ethyl)hyd razine-1 -carboxamide (compound I-2) & / V-((2- lsopropyl-5-methylphenyl)carbamothioyl)-1 -(1 -(5-(1 -(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4- triazol-3-yl)pyrazin-2-yl)ethyl)hydrazine-1 -carboxamide (compound I-3)

[0683] To a mixture of 2-(1-hydrazineylethyl)-5-(1-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazine (800 mg, 2.2 mmol) and phenyl N-(phenylcarbamothioyl)carbamate (791 mg, 2.4 mmol) in MeCN (8 mL) was added DIPEA (849 mg, 6.6 mmol) dropwise at room temperature. The reaction mixture was stirred at rt for 16 h. The mixture was quenched by the addition of water (10 mL), extracted with EtOAc (20 mL * 2). The organic layer was washed with brine (20 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by Prep-HPLC to afford N-((2-isopropyl-5- methylphenyl)carbamothioyl)-2-(1 -(5-(1 -(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2- yl)ethyl)hydrazine-1 -carboxamide (compound I-2) (185 mg, 14% yield) as a colorless solid.

[0684] LC-MS (ES) m / z = 600.3 (M+H)+.

[0685] 1H NMR (400 MHz, DMSO-cfe) <5 11.71 (s, 1 H), 9.72 (s, 1 H), 9.50 (s, 1 H), 9.35 (s, 1 H), 8.85 (s, 1 H), 8.13 (d, J = 10.8 Hz, 2H), 7.64 (d, J = 10.8 Hz, 2H), 7.22 (s, 2H), 7.08 (d, J = 10.8 Hz, 1 H), 6.00-5.65 (m, 1 H), 4.38 (s, 1 H), 2.91 (s, 1 H), 2.26 (s, 3H), 1.49 (s, 3H), 1.11 (s, 6H). and N-((2-isopropyl-5-methylphenyl)carbamothioyl)-1 -(1 -(5-(1 -(4-(trifluoromethoxy)phenyl) -1 H-1 ,2,4- triazol-3-yl)pyrazin-2-yl)ethyl)hydrazine-1 -carboxamide (compound I-3) (190 mg, 14% yield).

[0686] LC-MS (ES) m / z = 600.1 (M+H)+.

[0687] 1H NMR (400 MHz, DMSO-cfe) <5 11 .80 (s, 1 H), 10.07 (s, 1 H), 9.54 (s, 1 H), 9.31 (d, J = 1 .6 Hz, 1 H), 8.83 (d, J = 1 .2 Hz, 1 H), 8.12 (d, J = 8.8 Hz, 2H), 7.66 (d, J = 8.4 Hz, 2H), 7.24-7.21 (m, 2H), 7.10 (d, J = 8.0 120

[0688] Hz, 1 H), 5.78-5.76 (m, 1 H), 5.06 (s, 2H), 2.97-2.93 (m, 1 H), 2.26 (s, 3H), 1.66 (d, J = 7.6 Hz, 3H), 1.14 (d, J = 6.8 Hz, 6H).

[0689] Step 6. (Z)- / V-(3-(2-lsopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)-2-(1 -(5-(1 -(4- (trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)ethyl)hydrazine-1 -carboxamide (compound I-4)

[0690] To a mixture of N-((2-isopropyl-5-methylphenyl)carbamothioyl)-2-(1-(5-(1-(4-(trifluoromethoxy)phenyl)- 1 H-1 , 2, 4-triazol-3-yl)pyrazin-2-yl)ethyl)hydrazine-1 -carboxamide (150 mg, 0.3 mmol) and NaOAc (41 mg, 0.5 mmol) in EtOH (3 mL) was added ethyl 2-bromoacetate (84 mg, 0.5 mmol) dropwise at room temperature. The reaction mixture was stirred at 50°C for 5 h. The mixture was quenched by the addition of water (10 mL), extracted with EtOAc (15 mL * 2). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by Prep-HPLC to afford the title compound I-4 (30 mg, 19% yield).

[0691] LC-MS (ES) m / z = 640.0 (M+H)+.

[0692] 1H NMR (400 MHz, DMSO-cfe) 69.51 (s, 1 H), 9.18 (s, 1 H), 9.05 (dd, J = 4.0, 24.0 Hz, 1 H), 8.88 (s, 1 H), 8.11 (d, J = 8.0 Hz, 2H), 7.65 (d, J = 8.4 Hz, 2H), 7.29 (t, J = 8.4 Hz, 1 H), 7.18 (d, J = 8.0 Hz, 1 H), 6.94 (s, 1 H), 5.28 (s, 1 H), 4.32 (s, 1 H), 4.14-3.98 (m, 2H), 2.58-2.54 (m, 1 H), 2.23 (d, J = 9.6 Hz, 3H), 1.32 (d, J = 6.4 Hz, 3H), 1 .05-0.96 (m, 6H).

[0693] 121

[0694] Synthesis of compound I-5

[0695] Step-1 : Synthesis of 3-bromo-1-(4-chlorophenyl)-1 ,2,4-triazole:

[0696] To a stirred solution of 1-chloro-4-iodobenzene (5 g, 20.969 mmol, 1 equiv.) and 5-bromo-1 H-1 ,2,4- triazole (6.205 g, 41.938 mmol, 2 equiv.) in DMSO (50 mL) was added cesium carbonate (6.832 g, 20.969 mmol, 1 equiv.) and the reaction mixture was degassed with N2 gas for 5 min, then added copper iodide (0.399 g, 2.097 mmol, 0.1 equiv.) again degassed for another 5 min. The reaction mixture was stirred at 100 °C for 16 h. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic layer was washed with brine solution (100 mL), dried over anhydrous Na2SC>4 filtered and concentrated under reduced pressure. The crude material was purified by column chromatography using 30% ethyl acetate in petroleum ether as an eluent to afford the title compound (2 g, 37%).

[0697] LC-MS (m / z): 259.95 [M+H] + ion present

[0698] Step-1a: Synthesis of 1-(5-tributylstannylpyrazin-2-yl)ethanone:

[0699] To a stirred solution of 1-(5-chloropyrazin-2-yl)ethan-1-one (6 g, 38.322 mmol, 1 equiv.) and bis(tributyltin) (24.454 g, 42.154 mmol, 1.1 equiv.) in 1 ,4-dioxane (30 mL, 5V) were added palladium^ I) acetate (0.086 g, 0.383 mmol, 0.01 equiv.) and tricyclohexylphosphine (0.215 g, 0.766 mmol, 0.02 equiv.) at room temperature under N2 atmosphere. The resultant reaction mixture was stirred at 110 °C 122 for 5 h. Reaction mixture was filtered and concentrated under reduced pressure to get the crude product. The crude product was purified by column chromatography using silica gel (230-400 mesh) and 5% ethyl acetate in petroleum ether to afford the title compound (3 g, 19%).

[0700] LC-MS (m / z): 413.40 [M+H] + ion present

[0701] Step-2: Synthesis of 1-[5-[1-(4-chlorophenyl)-1 ,2,4-triazol-3-yl]pyrazin-2-yl]ethanone:

[0702] To a stirred solution of 3-bromo-1-(4-chlorophenyl)-1 H-1 ,2,4-triazole (1 g, 3.868 mmol, 1 equiv.) in NMP (10 mL, 10V) was added 1-(5-(tributylstannyl)pyrazin-2-yl)ethan-1-one (2.386 g, 5.803 mmol, 1.5 equiv.). The reaction mixture was degassed for 5 min. After that were added copper(l) oxide (0.277 g, 1.934 mmol, 0.5 equiv.), 1 ,3-Bis(diphenylphosphino)propane (0.160 g, 0.387 mmol, 0.1 equiv.) and palladium^ I) acetate (0.087 g, 0.387 mmol, 0.1 equiv.) at room temperature. The resultant reaction mixture was stirred at 120 °C for 4 h. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (2 x 100 mL) and washed with saturated brine solution (100 mL). The combined organic layer was dried over anhydrous sodium sulphate and concentrated to get the crude product. The crude product was purified by column chromatography using silica gel (230-400 mesh) and 30% ethyl acetate in petroleum ether to afford the title compound (1 g, 86%).

[0703] LC-MS (m / z): 300.38 [M+H] + ion present

[0704] Step-3: Synthesis of tert-butyl N-[1-[5-[1-(4-chlorophenyl)-1 ,2,4-triazol-3-yl]pyrazin-2- yl]ethylamino]carbamate:

[0705] To a solution of 1-(5-(1-(4-chlorophenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)ethan-1-one (1 g, 3.336 mmol, 1 equiv.) and tert-butyl carbazate (0.529 g, 4.004 mmol, 1.2 equiv.) in ethanol (10 mL). The reaction mixture was heated to 80 °C and maintained at the same temperature for 3 h. After that, the mixture was cooled, then acetic acid (0.601 g, 10.009 mmol, 3 equiv.) and sodium cyanoborohydride (1.258 g, 20.019 mmol, 6 equiv.) were added. The reaction mixture was stirred at 80°C for 32 h. The reaction mixture was quenched with saturated NaHCOs solution (100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic layer was washed with brine solution (100 mL), dried over anhydrous Na2SC>4 filtered and concentrated under vacuum to get the crude product. The crude product was purified by flash column chromatography using 60% ethyl acetate in petroleum ether as an eluent to afford tert-butyl tert-butyl N-[1-[5-[1-(4-chlorophenyl)-1 ,2,4-triazol-3-yl]pyrazin-2- yl]ethylamino]carbamate (0.900 g, 65%).

[0706] LC-MS (m / z): 416.20 [M+H] + ion present

[0707] Step-4: Synthesis of tert-butyl N-[1-[5-[1-(4-chlorophenyl)-1 ,2,4-triazol-3-yl]pyrazin-2-yl]ethyl- methyl-amino]carbamate:

[0708] To a stirred solution of tert-butyl 2-(1-(5-(1-(4-chlorophenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2- yl)ethyl)hydrazine-1-carboxylate (0.900 g, 2.164 mmol, 1 equiv.) and acetic acid (0.260 g, 4.328 mmol, 2 equiv.) in ethanol (9 mL) were added formaldehyde, ~37 wt% solution in water (0.263 mL, 3.246 mmol, 1.5 equiv) and sodium cyanoborohydride (0.272 g, 4.328 mmol, 2 equiv.) at room temperature and stirred at for 4 h. After completion of the reaction, the reaction mass was diluted with 123 water (50 mL) and extracted with ethyl acetate (2 x 50 mL). The combined organic layer and washed with brine (50 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to get crude material. The crude material was purified by flash column chromatography using 60% ethyl acetate in petroleum ether as an eluent to afford the title compound (0.700 g, 75%).

[0709] LC-MS (m / z): 430.75 [M+H] + ion present

[0710] Step-5: Synthesis of 1 -[1 -[5-[1 -(4-chlorophenyl)-1 ,2,4-triazol-3-yl]pyrazin-2-yl]ethyl]-1 -methyl- hydrazine-TFA salt:

[0711] To a stirred solution of tert-butyl 2-(1-(5-(1-(4-chlorophenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)ethyl)-2- methylhydrazine-1 -carboxylate (0.500 g, 1.163 mmol, 1 equiv.) in DCM (3.75 mL, 7.5 V) was added trifluoroacetic acid (1.25 mL, 2.5 V) at room temperature and stirred at same temperature for 5 h. Concentrated the reaction mixture under reduced pressure to get crude product. The crude product was triturated with pentane (5 mL) to afford the title compound (0.450 g, TFA salt).

[0712] LC-MS (m / z): 330.66 [M-CF3COOH+H] + ion present

[0713] Step-6: Synthesis of (3Z)-1 -[1 -[5-[1 -(4-chlorophenyl)-1 ,2,4-triazol-3-yl]pyrazin-2-yl]ethyl-methyl- amino]-3-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]urea (Compound I-5):

[0714] To a stirred solution of 1-[1-[5-[1-(4-chlorophenyl)-1 ,2,4-triazol-3-yl]pyrazin-2-yl]ethyl]-1-methyl- hydrazine-TFA salt (0.450 g, 1.052 mmol, 1 equiv) and 2-imino-3-(2-isopropyl-5-methyl- phenyl)thiazolidin-4-one (0.261 g, 1.052 mmol, 1 equiv.) in acetonitrile (4.5 mL, 10 V) were added N,N'- disuccinimidyl carbonate (0.323 g, 1.262 mmol, 1.2 equiv.) and N,N-diisopropylethylamine (0.583 mL, 3.156 mmol, 3 equiv.) at room temperature and stirred for 5 h at same temperature. The reaction mass was diluted with water (50 mL) and extracted with ethyl acetate (2 x 50 mL). The combined organic layer was washed with saturated brine solution (50 mL). Then the organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to get crude product. The crude product was purified by flash column chromatography using 10% MeOH in DCM to afford (Z)-2-(1-(5-(1-(4- chlorophenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)ethyl)-N-(3-(2-isopropyl-5-methylphenyl)-4- oxothiazolidin-2-ylidene)-2-methylhydrazine-1-carboxamide (0.3 g, 80% by LCMS). This material was re-purified by reverse phase preparative HPLC to afford Compound I-5 (0.135 g, 21 %).

[0715] Reverse phase preparative HPLC purification method:

[0716] Column / dimensions: X-bridge Phenyl C18 (19x250mm), 5 p

[0717] Mobile phase A: 10mM Ammonium bicarbonate in water

[0718] Mobile phase B: Acetonitrile

[0719] Gradient (Time / %B): 0 / 40,1 / 40,9 / 65,13 / 65,13.1 / 100,15 / 100,15.1 / 40,17 / 40 Flow rate: 17 ml / min

[0720] Solubility: ACN+THF+WATER

[0721] Analytical data:

[0722] LC-MS (m / z): 604.48 [M+H]+ion present 124

[0723] 1H NMR (400 MHz, DMSO-d6): 6 9.51 (s, 1 H), 9.22-9.11 (m, 1 H), 8.91-8.80 (m, 1 H), 8.72-8.62 (m, 1 H), 8.01 (d, J = 8.8 Hz, 2H), 7.70 (d, J = 8.8 Hz, 2H), 7.38-7.24 (m, 1 H), 7.19 (t, J = 6.2 Hz, 1 H), 6.94 (d, J = 5.2 Hz, 1 H), 4.23-3.92 (m, 3H), 2.49-2.37 (m, 4H), 2.25 (d, J = 4.4 Hz, 3H), 1.34-1.28 (m, 3H), 1.04 ((t, J = 7.6 Hz, 3H), 0.99-0.80 (m, 3H).

[0724] Compound 1-13 and 1-14 via chiral SFC-separation of compound I-4:

[0725] The mixture of isomers (E / Z)-N-(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)-2-(1-(5-(1- (4-(trifluoromethoxy)phenyl)-1 H-1 , 2, 4-triazol-3-yl)pyrazin-2-yl)ethyl)hydrazine-1 -carboxamide (Compound i-4, racemic) (0.600 g, 0.938 mmol, 1 equiv.) were separated by chiral SFC to get (E / Z)-N- (3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)-2-(1-(5-(1-(4-(trifluoromethoxy)phenyl)-1 H-

[0726] 1 .2.4-triazol-3-yl)pyrazin-2-yl)ethyl) hydrazine-1 -carboxamide (Isomer I) (240 mg, 40%) and (E / Z)-N-(3- (2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)-2-(1-(5-(1-(4-(trifluoromethoxy)phenyl)-1 H-

[0727] 1 .2.4-triazol-3-yl)pyrazin -2-yl)ethyl)hydrazine-1-carboxamide (Isomer II) (238 mg, 39%).

[0728] Chiral Preparative SFC method details:

[0729] Column / dimensions: CHIRALPAK IH (30*250) mm, 5p;

[0730] % CO2: 70%

[0731] % Co solvent: 30% (MeOH)

[0732] Flow: 100 ml / min

[0733] Back Pressure: 100 bar

[0734] Temperature: 30 °C

[0735] UV: 254 nm

[0736] Solubility: Methanol + Acetonitrile

[0737] Compound 1-13

[0738] LC-MS (m / z): 640.45 [M+H]+ion present

[0739] 1H NMR (400 MHz, DMSO-cfe): 6 9.51 (d, J = 1.2 Hz, 1 H), 9.21-9.16 (m, 1 H), 9.10-8.98 (m, 1 H), 8.87 (d, J = 1.2 Hz, 1 H), 8.14-8.06 (m, 2H), 7.65 (d, J = 8.8 Hz, 2H), 7.32-7.25 (m, 1 H), 7.18 (d, J = 8.0 Hz, 1 H), 6.93 (s, 1 H), 5.35-5.21 (m, 1 H), 4.38-4.23 (m, 1 H), 4.17-3.96 (m, 2H), 2.59-2.53 (m, 1 H), 2.24-2.21 (m, 3H), 1.38-1.23 (m, 3H), 1.05-0.92 (m, 6H).

[0740] Compound 1-14

[0741] LC-MS (m / z): 640.45 [M+H]+ion present

[0742] 1H NMR (400 MHz, DMSO-cfe): 6 9.51 (d, J = 1.2 Hz, 1 H), 9.21-9.16 (m, 1 H), 9.10-8.98 (m, 1 H), 8.87 (d, J = 1.2 Hz, 1 H), 8.14-8.06 (m, 2H), 7.65 (d, J = 8.8 Hz, 2H), 7.32-7.25 (m, 1 H), 7.18 (d, J = 8.0 Hz, 1 H), 6.93 (s, 1 H), 5.35-5.21 (m, 1 H), 4.38-4.24 (m, 1 H), 4.15-3.93 (m, 2H), 2.59-2.53 (m, 1 H), 2.24-2.20 (m, 3H), 1.35-1.25 (m, 3H), 1.05-0.92 (m, 6H). 125

[0743] Synthesis of 3-(5-(dimethylamino)-2-isopropylphenyl)-2-((-(5-(1 -(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4- triazol-3-yl)pyrazin-2-yl)methylene)hydrazineylidene)thiazolidin-4-one (Compound 1-19)

[0744] Step 1 : Synthesis of N-(5-(dimethylamino)-2-isopropylphenyl)-2-((5-(1-(4-(trifluoromethoxy)phenyl)-1 H- 1 ,2,4-triazol-3-yl)pyrazin-2-yl)methylene) hydrazine-1 -carbothioamide

[0745] To a stirred solution of 5-(1-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazine-2-carbaldehyde (1.4 g, 4.176 mmol, 1 equiv.) and N-(5-(dimethylamino)-2-isopropylphenyl)hydrazinecarbothioamide (1.159 g, 4.594 mmol, 1.1 equiv.) in methanol (28 mL) was added acetic acid (0.07 mL) at room temperature. The reaction mixture was stirred at the same temperature for 3 hours. The reaction mixture was concentrated under reduced pressure to afford the crude product. The crude product was triturated with diisopropyl ether (20 mL) to get the product (1 .2 g, 50%; LCMS: 92% purity). 400 mg of the crude product from 1.2 g was slurried with ethyl acetate (10 mL) to get N-(5-(dimethylamino)-2- isopropylphenyl)-2-((5-(1-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)methylene) hydrazine-1 -carbothioamide (240 mg, LCMS: 95% purity).

[0746] LC-MS (m / z): 570.28 [M+H]+ion present

[0747] 1H N MR (400 MHz, DMSO-d6): 6 12.13 (s, 1 H), 10.23 (s, 1 H), 9.75 (s, 1 H), 9.54 (s, 1 H), 9.30 (d, J = 1 .6 Hz, 1 H), 8.25 (s, 1 H), 8.16-8.09 (m, 2H), 7.65 (d, J = 8.4 Hz, 2H), 7.18 (d, J = 8.8 Hz, 1 H), 6.74 (dd, J = 8.8, 2.4 Hz, 1 H), 6.59 (d, J = 2.4 Hz, 1 H), 3.07-2.96 (m, 1 H), 2.88 (s, 6H), 1.15 (d, J = 6.8 Hz, 6H).

[0748] Step 2: Synthesis of 3-(5-(dimethylamino)-2-isopropylphenyl)-2-((-(5-(1-(4-(trifluoromethoxy)phenyl)- 1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)methylene)hydrazineylidene)thiazolidin-4-one

[0749] To a stirred solution of N-(5-(dimethylamino)-2-isopropylphenyl)-2-((5-(1-(4-(trifluoromethoxy)phenyl)- 1 H-1 , 2, 4-triazol-3-yl)pyrazin-2-yl)methylene)hydrazine-1 -carbothioamide (0.8 g, 1.404 mmol, 1 equiv.) in ethanol (8 mL) were added sodium acetate anhydrous (0.461 g, 5.618 mmol, 4 equiv.) and methyl 2- bromoacetate (0.199 mL, 2.107 mmol, 1 .5 equiv.) at room temperature. The reaction mixture was stirred at reflux temperature for 3 hours. After completion of the reaction, the reaction mixture was diluted with water (~30 mL), the precipitated solid was filtered to get the crude product. The crude product was triturated with 50% ethyl acetate in n-pentane (2 x 20 mL) to get 3-(5-(dimethylamino)-2- isopropylphenyl)-2-((-(5-(1 -(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2- yl)methylene)hydrazineylidene)thiazolidin-4-one (0.35 g, 41 %).

[0750] LC-MS (m / z): 610.60 [M+H]+ion present

[0751] 1H NMR (400 MHz, DMSO-d6): 6 9.56 (s, 1 H), 9.37 (d, J = 1 .6 Hz, 1 H), 9.24 (d, J = 1 .2 Hz, 1 H), 8.34 (s, 1 H), 8.15-8.06 (m, 2H), 7.66 (d, J = 8.4 Hz, 2H), 7.29 (d, J = 8.8 Hz, 1 H), 6.86 (dd, J = 8.8, 2.8 Hz, 1 H), 126

[0752] 6.61 (d, J= 2.4 Hz, 1H), 4.28 (d, J= 17.6 Hz, 1H), 4.16 (d, J= 17.2 Hz, 1H), 2.89 (s, 6H), 2.69-2.58 (m, 1H), 1.12 (d, J = 6.8 Hz, 3H), 1.08 (d, J = 6.8 Hz, 3H). Compounds I 127 128 129 130 131

[0753] (E / Z)-1-(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)-3-(5-(1-methyl-5-(4-

[0754] (trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)urea (Compound 11-1): 132

[0755] Step 1 a: Synthesis of tert-butyl (5-bromopyrazin-2-yl) carbamate:

[0756] To a stirred solution of 5-bromopyrazin-2-amine (10 g, 57.5 mmol, 1 equiv.) in methylene chloride (1.6 mL) were added 4-dimethylaminopyridine (7.021 mg, 5.7 mmol, 0.1 equiv.) and di-tert-butyl dicarbonate (125.430 mg, 57.5 mmol, 1 equiv.) solution in methylene chloride (DCM) (16 mL) drop wise at 0°C. Then the reaction mixture was slowly allowed to warm to room temperature and stirred at the same temperature for 6 h. After completion of the reaction, water (100 mL) was added and the mixture was extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulphate and concentrated to get the crude product, which was purified by silica gel column chromatography using 5% ethyl acetate in petroleum ether as eluent to get tert-butyl (5-bromopyrazin-2-yl) carbamate (11 g, 70%).

[0757] LC-MS (m / z): 272.29 [M-H]’ ion present

[0758] Step 1 b: Synthesis of tert-butyl (5-(tributylstannyl)pyrazin-2-yl)carbamate:

[0759] To a stirred solution of tert-butyl (5-bromopyrazin-2-yl) carbamate (6 g, 21.889 mmol, 1 equiv.) and bis(tributyltin) (13.968 g, 24.078 mmol, 1 .1 equiv.) in 1 ,4- dioxane (30 mL) were added palladium^ I) acetate (0.049 g, 0.219 mmol, 0.01 equiv.) and tricyclohexylphosphine (0.123 g, 0.438 mmol, 0.02 equiv.) at room temperature under nitrogen atmosphere. The resultant reaction mixture was stirred at 110°C for 4 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to get the crude product, which was purified by silica gel (230-400 mesh) column chromatography using 5% ethyl acetate in petroleum ether to get tert-butyl (5-(tributylstannyl)pyrazin-2- yl)carbamate (3.6 g, 34%).

[0760] LC-MS (m / z): 486.75 [M+H]+ion present

[0761] Step 1 : Synthesis of 3-bromo-1-methyl-5-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazole:

[0762] To a stirred solution of 3,5-dibromo-1-methyl-1 H-1 ,2,4-triazole (5.0 g, 20.757 mmol, 1.0 equiv.) and (4- (trifluoromethoxy)phenyl)boronic acid (3.420 g, 16.606 mmol, 0.8 equiv.) in a mixture of 1 ,4-dioxane (100 mL) and water (25 mL) was added potassium carbonate (8.606 g, 62.271 mmol, 3.0 equiv.) at room temperature and degassed with nitrogen for 5 min. After that, tetrakis(triphenylphosphine)palladium(0) (1.199 g, 1.038 mmol, 0.05 equiv.) was added to the reaction mixture and heated at 100°C for 16 h. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (2x 50 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulphate, filtered and concentrated to get the crude product, which was purified by silica gel column chromatography using 10% of ethyl acetate in petroleum ether to get 3-bromo-1- methyl-5-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazole (2 g, 30%).

[0763] LC-MS (m / z): 322.41 [M+H]+ion present

[0764] Step 2: Synthesis of 5-(1 -methyl-5-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-amine: 133

[0765] To a stirred solution of 3-bromo-1-methyl-5-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazole (1.8 g, 5.589 mmol, 1.0 equiv.) and tert-butyl (5-(tributylstannyl)pyrazin-2-yl)carbamate (3.518 g, 7.265 mmol, 1.3 equiv.) in NMP (18 mL). The reaction mixture was degassed for 5 min. Afterthat, copper(ll) oxide (0.222 g, 2.794 mmol, 0.5 equiv.), 1 ,3-bis(diphenylphosphino)propane (dppp) (0.231 g, 0.559 mmol, 0.1 equiv.) and palladium^ I) acetate (0.125 g, 0.559 mmol, 0.1 equiv.) were added to the reaction mixture at room temperature. The resultant reaction mixture was stirred at 120°C for 16 h. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layer was washed with brine (10 mL), dried over anhydrous sodium sulphate and concentrated to get the crude product, which was purified by silica gel column chromatography (230-400 mesh) using 10% MeOH in DCM as eluent to get 5-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin- 2-amine (1 .2 g, 64%).

[0766] LC-MS (m / z): 337.48 [M+H]+ion present

[0767] Step 3: Synthesis of phenyl (5-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2- yl)carbamate:

[0768] To a stirred solution of 5-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-amine (0.95 g, 2.825 mmol, 1 equiv.) in dichloromethane (19 mL) were added pyridine (2.280 mL, 28.250 mmol, 10 equiv.) and phenyl chloroformate (2.654 g, 16.950 mmol, 6 equiv.) solution in dichloromethane (4.750 mL) at 0°C. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was quenched with 1 N hydrogen chloride solution in water (20 mL) and extracted with dichloromethane (2x 10 mL). The combined organic layers were washed with sat.aq. NaHCCh solution (2 x 10 mL) and brine (10 mL), dried over anhydrous sodium sulphate, filtered and concentrated to get the crude product, which was triturated with pet ether (10 mL) to get phenyl (5-(1-methyl-5-(4-(trifluoromethoxy)phenyl)- 1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)carbamate (0.75 g, 58%).

[0769] LC-MS (m / z): 457.73 [M+H]+ion present

[0770] Step 4: Synthesis of (E / Z)-1 -(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)-3-(5-(1 -methyl- 5-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)urea (Compound 11-1):

[0771] To a stirred solution of phenyl (5-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin- 2-yl)carbamate (0.5 g, 1.096 mmol, 1.0 equiv.) and 2-imino-3-(2-isopropyl-5-methylphenyl)thiazolidin-4- one (0.326 g, 1.315 mmol, 1 .2 equiv.) in tetrahydrofuran (10 mL) was added A / , / V-diisopropylethylamine (0.950 mL, 5.478 mmol, 5 equiv.) at room temperature. The reaction mixture was stirred at 70°C for 16 h. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (2x 20 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulphate, filtered and concentrated to get the crude product, which was purified by silica gel chromatography using 50% of ethyl acetate in petroleum ether as eluent to get (E / Z)-1-(3-(2-isopropyl-5-methylphenyl)-4- oxothiazolidin-2-ylidene)-3-(5-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2- yl)urea (0.3 g, 45%). 134

[0772] LC-MS (m / z): 611.30 [M+H]+ion present

[0773] 1H NMR (400 MHz, DMSO-d6): 6 10.69 (s, 1 H), 9.23 (s, 1 H), 8.92 (d, J = 1.6 Hz, 1 H), 8.05-7.98 (m, 2H), 7.60 (d, J = 8.4 Hz, 2H), 7.39 (d, J = 8.0 Hz, 1 H), 7.28 (d, J = 8.0 Hz, 1 H), 7.06 (d, J = 0.8 Hz, 1 H), 4.28 (d, J = 18.0 Hz, 1 H), 4.13 (d, J = 18.4 Hz, 1 H), 4.07 (s, 3H), 2.69-2.61 (m, 1 H), 2.32 (s, 3H), 1.16 (d, J = 6.8 Hz, 3H), 1.09 (d, J = 6.8 Hz, 3H).

[0774] Synthesis of (E / Z)-1-(3-(5-methyl-2-((2,2,2-trifluoroethoxy)methyl)phenyl)-4-oxothiazolidin-2-ylidene)- 3-(5-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)urea (Compound 11-4):

[0775] Step 1 : Synthesis of (4-methyl-2-nitrophenyl)methanol:

[0776] To a solution of 4-methyl-2-nitrobenzoic acid (20 g, 110.406 mmol, 1 equiv.) in tetrahydrofuran (200 mL) was added borane - tetrahydrofuran complex (1 M in tetrahydrofuran) (154.568 mL, 154.568 mmol, 1.4 equiv.) at 0 °C, and the reaction mixture was stirred at 70°C for 4 h. Then cooled to room temperature and quenched slowly with saturated sodium bicarbonate solution (500 mL) and extracted with EtOAc (2 x 300 mL). The organic layer was washed with brine (200 mL) and dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to get the crude compound. The crude product was purified by column chromatography (silica gel 100-200 mesh) eluting with 20% EtOAc-petroleum ether to get (4-methyl-2-nitrophenyl)methanol (16 g, 87%).

[0777] Step 2: Synthesis of 4-methyl-2-nitro-1-((2,2,2-trifluoroethoxy)methyl)benzene:

[0778] To a solution of (4-methyl-2-nitrophenyl)methanol (6 g, 35.893 mmol, 1 equiv.) in tetrahydrofuran (60 mL) was added sodium hydride, 60% dispersion in mineral oil (2.871 g, 71.787 mmol, 2 equiv.) portionwise at 0°C, and the reaction mixture was stirred for 30 min. 2,2,2-Trifluoroethyl trifluoromethanesulfonate (16.662 g, 71.787 mmol, 2 equiv.) was added drop-wise, and the reaction mixture was stirred at room temperature for 2 h.. The reaction mixture was quenched with ice-cold water (300 mL) and extracted with ethyl acetate (2 x 300 mL). The organic layer was washed with brine (500 mL) and dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to get crude product (7.5 g), which was mixed with another 10 g batch and combinedly purified by column 135 chromatography (silica gel 230-400 mesh) eluting with 3-4% EtOAc-petroleum ether to get 4-methyl-2- nitro-1-((2,2,2-trifluoroethoxy)methyl)benzene (5.4 g, 23%).

[0779] Step 3: Synthesis of 5-methyl-2-((2,2,2-trifluoroethoxy)methyl)aniline:

[0780] To a stirred solution of 4-methyl-2-nitro-1-((2,2,2-trifluoroethoxy)methyl)benzene (5.4 g, 21 .670 mmol, 1 equiv.) in ethanol (37.8 mL) and ethyl acetate (37.8 mL) was added palladium 10% on carbon (50% wet basis) (4.612 g) under nitrogen atmosphere. The heterogeneous mixture was placed under an atmosphere of hydrogen (15 psi) and stirred at room temperature for 16 h (reaction followed by TLC). After completion of reaction, the reaction mixture was filtered and concentrated onto celite bed and concentrated under reduced pressure to get crude product. The crude product was purified by column chromatography (silica gel 100-200 mesh) eluting with 6-7% EtOAc-petroleum ether to get 5-methyl-2- ((2,2,2-trifluoroethoxy)methyl)aniline (4.3 g, 91 %).

[0781] LC-MS (m / z): 220.09 [M+H]+ion present

[0782] Step 4: Synthesis of 2-chloro-N-(5-methyl-2-((2,2,2-trifluoroethoxy)methyl)phenyl)acetamide:

[0783] To a solution of 5-methyl-2-((2,2,2-trifluoroethoxy)methyl)aniline (4.3 g, 19.616 mmol, 1 equiv.) in ethyl acetate (43 mL) were added sodium bicarbonate (4.120 g, 49.040 mmol, 2.5 equiv.) and 2-chloroacetyl chloride (1.899 mL, 23.539 mmol, 1.2 equiv.) drop-wise at 0°C, and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was quenched with water (100 mL) and was extracted with EtOAc (2 x 100 mL). The organic layer was dried over anhydrous Na2SC>4, filtered and concentrated under reduced pressure to afford 2-chloro-N-(5-methyl-2-((2,2,2- trifluoroethoxy)methyl)phenyl)acetamide (5.8 g crude), which was used directly for next step.

[0784] LC-MS (m / z): 296.63 [M+H]+ion present

[0785] Step 5: Synthesis of 2-imino-3-(5-methyl-2-((2,2,2-trifluoroethoxy)methyl)phenyl)thiazolidin-4-one:

[0786] To a stirred solution of 2-chloro-N-(5-methyl-2-((2,2,2-trifluoroethoxy)methyl)phenyl)acetamide (5.8 g, 19.615 mmol, 1 equiv.) in acetone (46.4 mL) was added potassium thiocyanate, 98% (3.81 g, 39.231 mmol, 2 equiv.). The reaction mixture was stirred at 55°C for 3 h. The reaction mixture was cooled to room temperature and cesium carbonate (1.278 g, 3.923 mmol, 0.2 equiv.) was added. Then, the reaction mixture was stirred at room temperature for 30 min. After completion of the reaction, the reaction mixture was filtered over a celite bed and concentrated under reduced pressure to get crude product. The crude product was purified by column chromatography (silica gel 100-200 mesh) using 35% ethyl acetated in petroleum ether to get product. The product was further re-purified by achiral SFC method. The clean fractions were concentrated to get 2-imino-3-(5-methyl-2-((2,2,2- trifluoroethoxy)methyl)phenyl)thiazolidin-4-one (2.8 g, 45%).

[0787] LC-MS (m / z): 319.27 [M+H]+ion present 136

[0788] 1H NMR (400 MHz, DMSO-d6): 6 9.25 (s, 1 H), 7.40 (d, J = 7.6 Hz, 1 H), 7.29 (d, J = 7.6 Hz, 1 H), 7.03 (s, 1 H), 4.46 (dd, J = 18.8, 12.8 Hz, 2H), 4.14 (s, 2H), 3.94 (q, J = 9.2 Hz, 2H), 2.33 (s, 3H).

[0789] Step 1 : Synthesis of (E / Z)-1-(3-(5-methyl-2-((2,2,2-trifluoroethoxy)methyl)phenyl)-4-oxothiazolidin-2- ylidene)-3-(5-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)urea (Compound il-4):

[0790] To a stirred solution of phenyl (5-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin- 2-yl)(phenoxycarbonyl)carbamate (1 g crude, 1.735 mmol, 1.0 equiv.) and 2-imino-3-(5-methyl-2- ((2,2,2-trifluoroethoxy)methyl)phenyl)thiazolidin-4-one (0.663 g, 2.082 mmol, 1.2 equiv.) in tetrahydrofuran (20 mL) was added A / , / V-diisopropylethylamine (1 .505 mL, 8.673 mmol, 5.0 equiv.) at room temperature. The reaction mixture was stirred at 70°C for 16 h. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (2x 20 mL). The combined organic layer was washed with brine (10 mL), dried over anhydrous sodium sulphate, filtered and concentrated to get the crude product. The crude product was purified by silica gel chromatography (50% of ethyl acetate in petroleum ether) followed by re-purified with reverse phase preparative HPLC to get (E / Z)-1-(3-(5- methyl-2-((2,2,2-trifluoroethoxy)methyl)phenyl)-4-oxothiazolidin-2-ylidene)-3-(5-(1-methyl-5-(4- (trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)urea (0.24 g, 16%).

[0791] LC-MS (m / z): 681.47 [M+H]+ion present

[0792] 1H NMR (400 MHz, DMSO-d6): 6 10.72 (s, 1 H), 9.26 (s, 1 H), 8.93 (d, J = 1.2 Hz, 1 H), 8.09-7.97 (m, 2H), 7.60 (d, J = 8.0 Hz, 2H), 7.45 (d, J = 8.0 Hz, 1 H), 7.34 (d, J = 7.6 Hz, 1 H), 7.19 (s, 1 H), 4.61-4.50 (m, 2H), 4.14 (s, 2H), 4.07 (s, 3H), 4.03-3.92 (m, 2H), 2.37 (s, 3H).

[0793] Synthesis of N-[5-methyl-2-(propan-2-yl)phenyl]-1 -{[(5-{1 -methyl-5-[4-(trifluoromethoxy)phenyl]-1 H-

[0794] 1 ,2,4-triazol-3-yl}pyrazin-2-yl)carbamoyl]amino}methane thioamide (Compound il-5):

[0795] Synthesis of 1-(2-isopropyl-5-methylphenyl)thiourea:

[0796] To 2-isopropyl-5-methylaniline (10 g, 67.008 mmol, 1 equiv.) in acetone (200 mL) was added benzoyl isothiocyanate (10.935 g, 67.008 mmol, 1 equiv.). The reaction was heated at 50°C and maintained for 137

[0797] 8 h at this temperature. Then the reaction mass was concentrated, to the concentrated reaction mass was added methanol (200 mL) and 2M aqueous sodium hydroxide solution (400 mL) and heated at 65°C for 3 h. After completion of the reaction, the mixture was concentrated, diluted with water (100 mL) and neutralized with 2M HCI. After filtration, the reaction mass was concentrated and dried in vacuum to provide the title compound as a tan solid. The crude product was further purified by silica gel (230- 400 mesh) column chromatography using 40% ethyl acetate in petroleum ether and obtained 1-(2- isopropyl-5-methylphenyl)thiourea (11 g, 79% yield).

[0798] LC-MS (m / z): 209.1 [M+H]+ion present

[0799] Compound II-5

[0800] Step 1 : Synthesis of N-[5-methyl-2-(propan-2-yl)phenyl]-1 -{[(5-{1 -methyl-5-[4-(trifluoromethoxy)phenyl]- 1 H-1 ,2,4-triazol-3-yl}pyrazin-2-yl)carbamoyl]amino}methane thioamide (Compound II-5):

[0801] To a stirred solution of phenyl (5-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin- 2-yl)carbamate (1.0 g, 2.191 mmol, 1.0 equiv.) and 1-(2-isopropyl-5-methylphenyl)thiourea (0.685 g, 3.287 mmol, 1.5 equiv.) (synthesized following the protocol adapted for ES5104-1) in N,N- dimethylformamide (10 mL) was added cesium carbonate (2.142 g, 6.573 mmol, 3.0 equiv.) at room temperature. The reaction mixture was stirred at the same temperature for 4 . The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (2 x20 mL). The combined organic layer was washed with brine (10 mL), dried over anhydrous sodium sulphate, filtered and concentrated to get the crude product. The crude product was purified by silica gel chromatography (50% of ethyl acetate in petroleum ether) followed by re-purified with reverse phase preparative HPLC to get N-[5-methyl-2- (propan-2-yl)phenyl]-1 -{[(5-{1 -methyl-5-[4-(trifluoromethoxy)phenyl]-1 H-1 ,2,4-triazol-3-yl}pyrazin-2- yl)carbamoyl]amino}methane thioamide (0.063 g, 5%).

[0802] LC-MS (m / z): 571.40 [M+H]+ion present

[0803] 1 H NMR (400 MHz, DMSO-d6): 6 11.51 (s, 1 H), 10.75 (s, 1 H), 10.18 (s, 1 H), 9.21 (s, 1 H), 9.00 (d, J = 0.8 Hz, 1 H), 8.03 (d, J = 8.8 Hz, 2H), 7.61 (d, J = 8.0 Hz, 2H), 7.27 (d, J = 8.0 Hz, 1 H), 7.22-7.09 (m, 2H), 4.08 (s, 3H), 3.07-2.97 (m, 1 H), 2.29 (s, 3H), 1.18 (d, J = 6.8 Hz, 6H).

[0804] Synthesis of (E / Z)-2-(1 -(5-(5-(4-chlorophenyl)-1 -methyl- 1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)ethyl)-N-(3- (2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)hydrazine-1 -carboxamide (Compound 11-6) : 138

[0805] Step-1 : Synthesis of 3-bromo-5-(4-chlorophenyl)-1 -methyl- 1 H-1 ,2,4-triazole

[0806] To a stirred solution of 3, 5-dibromo-1-methyl-1 H-1 ,2,4-triazole (5 g, 20.757 mmol, 1 equiv.) in 1 ,4- dioxane (100 mL, 20 V) were added (4-chlorophenyl)boronic acid (2.597 g, 16.606 mmol, 0.8 equiv.), potassium carbonate (8.606 g, 62.271 mmol, 3.0 equiv.) and water (25 mL, 5 V) at room temperature. The reaction mixture was degassed with nitrogen at room temperature for 15 min. After that, tetrakis(triphenylphosphine)palladium(0) (1.199 g, 1.038 mmol, 0.05 equiv.) was added to reaction mixture and again degassed with nitrogen gas another 15 min. The reaction mixture was heated to 100°C and maintained for 16 h at the same temperature. After completion of the reaction, the mixture was cooled to room temperature and the layers were separated. The organic layer was concentrated to get the crude product, which was purified by silica gel (230-400 mesh) column chromatography using 20% ethyl acetate in petroleum ether to afford 3-bromo-5-(4-chlorophenyl)-1-methyl-1 H-1 ,2,4-triazole (2.6 g, 46%).

[0807] LC-MS (m / z): 274.24 [M+H]+ion present

[0808] Step-2: Synthesis of 1 -(5-(5-(4-chlorophenyl)-1 -methyl- 1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)ethan-1 -one: A stirred solution of 3-bromo-5-(4-chlorophenyl)-1-methyl-1 H-1 ,2,4-triazole (1 .7 g, 6.238 mmol, 1 equiv.) and 1-(5-(tributylstannyl)pyrazin-2-yl)ethan-1-one (2.950 g, 7.174 mmol, 1.15 equiv.) in N-methyl-2- pyrrolidinone (17 mL, 10 V) was degassed with nitrogen about 10 mi. After that, were added copper(l) oxide (0.446 g, 3.119 mmol, 0.5 equiv.), 1 ,3-bis(diphenylphosphino)propane (0.257 g, 0.624 mmol, 0.1 equiv.) and palladium (II) acetate (0.140 g, 0.624 mmol, 0.1 equiv.) at room temperature and again degassed with nitrogen about 10 min. The resultant reaction mixture was stirred at 80°C for 16 h. After completion of the reaction, the mixture was quenched with saturated sodium bicarbonate solution 139

[0809] (10 mL), diluted with water (85 mL) and extracted with dichloromethane (2 x 100 mL). The combined organic layers were washed with saturated brine solution (100 mL), dried over anhydrous sodium sulphate and concentrated to get the crude product. The crude product was purified by column chromatography using silica gel (230-400 mesh) and 40% ethyl acetate in petroleum ether to afford 1- (5-(5-(4-chlorophenyl)-1-methyl-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)ethan-1-one (0.52 g, 27%).

[0810] LC-MS (m / z): 314.17 [M+H]+ion present

[0811] Step-3: Synthesis of (E)-2-(1-(5-(5-(4-chlorophenyl)-1-methyl-1 H-1 ,2,4-triazol-3-yl)pyrazin-2- yl)ethylidene)hydrazine-1 -carboxylate:

[0812] To a solution of 1-(5-(5-(4-chlorophenyl)-1-methyl-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)ethan-1-one (0.52 g, 1.657 mmol, 1 equiv. ) in ethanol (5.200 mL, 10 V) was added tert-butyl carbazate (0.329 g, 2.486 mmol, 1 .5 equiv.) at room temperature The reaction mixture was heated to 80°C and stirred for 8 h at the same temperature. After completion of the reaction, the reaction mixture was cooled to 0°C and filtered to collect the solid, which was washed with cold ethanol (2 x 1 mL) to afford tert-butyl (E)-2-(1- (5-(5-(4-chlorophenyl)-1 -methyl- 1 H-1 , 2, 4-triazol-3-yl)pyrazin-2-yl)ethylidene)hydrazine-1 -carboxylate (0.6 g, 85%).

[0813] LC-MS (m / z): 428.75 [M+H]+ion present

[0814] Step-4: Synthesis of tert-butyl 2-(1-(5-(5-(4-chlorophenyl)-1-methyl-1 H-1 ,2,4-triazol-3-yl)pyrazin-2- yl)ethyl)hydrazine-1 -carboxylate:

[0815] To a solution of tert-butyl (E)-2-(1-(5-(5-(4-chlorophenyl)-1-methyl-1 H-1 ,2,4-triazol-3-yl)pyrazin-2- yl)ethylidene)hydrazine-1 -carboxylate (0.45 g, 1.052 mmol, 1 equiv.) in methanol (4.500 mL, 10 V) were added sodium cyanoborohydride (0.661 g, 10.517 mmol, 10 equiv.) and acetic acid (1 .575 mL, 3.5 V) at room temperature. The reaction mixture was heated to 70°C and stirred for 16 h at that temperature. After completion of the reaction, the mixture was quenched with saturated sodium bicarbonate solution (50 mL) at 0°C and extracted with dichloromethane (2 x 50 mL). The combined organic layers were concentrated under reduced pressure to afford tert-butyl 2-(1-(5-(5-(4-chlorophenyl)-1-methyl-1 H- 1 ,2, 4-triazol-3-yl)pyrazin-2-yl)ethyl)hydrazine-1 -carboxylate (0.398 g, 86%).

[0816] LC-MS (m / z): 430.76 [M+H]+ion present.

[0817] Step-5: Synthesis of 2-(5-(4-chlorophenyl)-1-methyl-1 H-1 ,2,4-triazol-3-yl)-5-(1- hydrazineylethyl)pyrazine TFA salt:

[0818] To a solution of tert-butyl 2-(1-(5-(5-(4-chlorophenyl)-1-methyl-1 H-1 ,2,4-triazol-3-yl)pyrazin-2- yl)ethyl)hydrazine-1 -carboxylate (0.39 g, 0.907 mmol, 1 equiv.) in dichloromethane (7.800 mL, 20 V) was added trifluoroacetic acid (1.560 mL, 4 V) at 0°C. Then the reaction mixture stirred at room temperature for 6 h. After completion of the reaction, the reaction mixture was concentrated, and the crude product was triturated with mixture of tert-butyl methyl ether and n-pentane (1 :1) (10 mL). The 140 resulting residue was washed with petrol ether (2 x 10 mL) and dried under reduced pressure to afford 2-(5-(4-chlorophenyl)-1-methyl-1 H-1 ,2,4-triazol-3-yl)-5-(1-hydrazineylethyl)pyrazine TFA salt (0.388 g).

[0819] LC-MS (m / z): 330.50 [M+H-TFA]+ion present

[0820] Step-6: Synthesis of (E / Z)-2-(1 -(5-(5-(4-chlorophenyl)-1 -methyl- 1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)ethyl)- N-(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)hydrazine-1 -carboxamide (Compound II- 6):

[0821] To a stirred solution of 2-(5-(4-chlorophenyl)-1-methyl-1 H-1 ,2,4-triazol-3-yl)-5-(1- hydrazineylethyl)pyrazine TFA salt (0.388 g, 0.874 mmol, 1 equiv.) and 4-nitrophenyl (Z)-(3-(2- isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate (lnt-3 from ES5293-9) (synthesized following the protocol adapted for ES5293-9-Batch-2) (0.398 g, 0.962 mmol, 1.1 equiv.) in tetrahydrofuran (3.88 mL, 10 V) was added N,N-diisopropylethylamine (1.13 g, 8.742 mmol, 10 equiv.) at room temperature. The resulting reaction mixture was stirred at 70°C for 12 h. After completion of the reaction, the reaction mixture was concentrated to get crude product. The crude product was purified by silica gel column chromatography (230-400 mesh) using 90% ethyl acetate in petroleum ether and further re-purified by reverse phase preparative HPLC and lyophilized to get (E / Z)-2-(1-(5-(5- (4-chlorophenyl)-1-methyl-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)ethyl)-N-(3-(2-isopropyl-5-methylphenyl)-4- oxothiazolidin-2-ylidene)hydrazine-1-carboxamide (114 mg, 22%).

[0822] 1H NMR (400 MHz, DMSO-c / 6): 6 9.15-8.99 (m, 2H), 8.83 (d, J = 1.2 Hz, 1 H), 7.90 (dd, J = 8.8, 2.0 Hz, 2H), 7.68 (dd, J = 8.8, 1.2 Hz, 2H), 7.30 (t, J = 8.0 Hz, 1 H), 7.18 (d, J = 8.0 Hz, 1 H), 6.94 (s, 1 H), 5.31- 5.18 (m, 1 H), 4.33-4.23 (m, 1 H), 4.17-4.04 (m, 4H), 4.03-3.91 (m, 1 H), 2.58-2.53 (m, 1 H), 2.29-2.19 (m, 3H), 1.35-1.26 (m, 3H), 1.08-0.92 (m, 6H).

[0823] Step 1 a: Synthesis of (E / Z)-(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate

[0824] To a stirred solution of 2-imino-3-(2-isopropyl-5-methylphenyl)thiazolidin-4-one (0.5 g, 2.013 mmol, 1 equiv.) in acetonitrile (4 mL, 8 V) was added cesium carbonate (0.525 g, 1.611 mmol, 0.8 equiv.) at room temperature. After that 4-nitrophenyl carbonochloridate (0.406 g, 2.013 mmol, 1 equiv.) in acetonitrile (1 mL, 2 V) was added dropwise at room temperature. The resultant reaction mixture was stirred for 1 h at same temperature. After completion of the reaction, the reaction mass was diluted with water (5 mL) and extracted the product with ethyl acetate (2 X 10 mL). The combined organic layer was washed with saturated brine solution (5 mL), then dried over anhydrous sodium sulphate, filtered and concentrated to get crude product. Obtained crude product was washed with n-pentane (2 X 5 mL) and 141 dried in rotatory evaporator at 40°C for 20 min to get 4-nitrophenyl (E / Z)-(3-(2-isopropyl-5- methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate (810 mg, 97%).

[0825] LC-MS (m / z): 414.10 [M+H]+ ion present

[0826] Synthesis of (E / Z)-N-(3-(5-methyl-2-((2,2,2-trifluoroethoxy)methyl)phenyl)-4-oxothiazolidin-2-ylidene)- 2-(1 -(5-(1 -methyl-5-(4-(trifluoromethoxy)phenyl)-1 H-1 ,2,4-triazol-3-yl)pyrazin-2-yl)ethyl)hydrazine-1 - carboxamide (Compound il-8):

[0827] Step 1 a: Synthesis of 4-nitrophenyl (E / Z)-(3-(5-methyl-2-((2,2,2-trifluoroethoxy)methyl)phenyl)-4- oxothiazolidin-2-ylidene)carbamate:

[0828] To a stirred solution of 2-imino-3-(5-methyl-2-((2,2,2-trifluoroethoxy)methyl)phenyl)thiazolidin-4-one (2 g, 6.283 mmol, 1.0 equiv.) in acetonitrile (16 mL) were added cesium carbonate (1.638 g, 5.026 mmol, 0.8 equiv.) and 4-nitrophenyl carbonochloridate (1 .266 g, 6.283 mmol, 1 .0 equiv.) solution in acetonitrile (4 mL) slowly at room temperature. The reaction mixture was stirred at same temperature for 1 h. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (2 x 30 mL). The combined organic layer was washed with saturated brine (10 mL), then dried over anhydrous sodium sulphate, filtered and concentrated to get the crude product. The crude product was washed with n- pentane (2 x 5 mL) to get 4-nitrophenyl (E / Z)-(3-(5-methyl-2-((2,2,2-trifluoroethoxy)methyl)phenyl)-4- oxothiazolidin-2-ylidene)carbamate (2.5 g, 82%).

[0829] LC-MS (m / z): 484.65 [M+H]+ion present

[0830] Step 1 : Synthesis of (E / Z)-N-(3-(5-...

Claims

153Claims1. Compound of formula I whereinB1is CRB1;B2is CRB2;RB1and RB2independently of each other are H, halogen, N3, OH, CN, NO2, -SCN, -SF5, Ci-Ce-alkyl, C1- Ce-alkoxy, C2-C6-alkenyl, tri-Ci-Ce-alkylsilyl, C2-Ce-alkynyl, Ci-Ce-alkoxy-Ci-C4-alkyl, Ci-Ce- alkoxy-Ci-C4-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, C1-C4- alkyl-Cs-Ce-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,C(=O)-ORa, NRbRc, Ci-C6-alkylene-NRbRc, O-Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, NH-C1- C6-alkylene-NRbRc, C(=O)-NRbRc, C(=O)-Rd, SO2NRbRc, or S(=O)mRe, phenyl, phenoxy, phenylcarbonyl, phenylthio, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with one or more Rf;R2and R3are H, Ci-Ce-alkyl, C2-C6-alkenyl, C2-Ce-alkynyl, Ci-Ce-alkoxy-Ci-C4-alkyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(=O)-ORa, Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, C(=O)-NRbRc, C(=O)-Rd, SO2NRbRc, S(=O)mRe, phenyl, -CH2-C(=O)-ORa, -CH2-phenyl, or 5-6-membered hetaryl, wherein the phenyl or hetaryl ring is unsubstituted or substituted with one or more RAr; wherein at least one of R2and R3is phenyl or 5- or 6-membered hetaryl unsubstituted or substituted with one or more RAr; wherein each RAris independently selected from halogen, N3, OH, CN, NO2, -SCN, -SF5, Ci-Ce-alkyl, C1- Ce-alkoxy, C2-Ce-alkenyl, tri-Ci-Ce-alkylsilyl, C2-Ce-alkynyl, Ci-Ce-alkoxy-Ci-C4-alkyl, C1- Ce-alkoxy-Ci-C4-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-cycloalkoxy, C3-Ce-cycloalkyl-Ci-C4-alkyl, C3-Ce-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(=O)-ORa, NRbRc, Ci-C6-alkylene-NRbRc, O-Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, NH-Ci-C6-alkylene-NRbRc, C(=O)-NRbRc, C(=O)-Rd, SO2NRbRc, or S(=O)mRe, phenyl, phenoxy, phenylcarbonyl, phenylthio or -CH2-phenyl, wherein phenyl rings are unsubstituted or substituted with one or more Rf, or two RArcombine to form together with the atoms to which they are attached a 5- to 6-membered carbo- or heterocyclic ring unsubstituted or substituted with one or more Rf; m is 0, 1 , or 2;R1is a moiety of formula X-Y-Z-T-R4; whereinX is a single bond;154-(C(Rxa)2)P-, wherein p is an integer of 1 to 3, preferably 1 or 2;-(C(Rxa)2)o-NRxc-, wherein o is an integer of 1 or 2 and N is bound to Y; or-NRXC-;Y is -CRya=N-, wherein the N is bound to Z;-NRyc-C(=O)-, wherein C(=O) is bound to Z; or -NRyc-C(=S)-, wherein C(=S) is bound to Z;Z is -NRZC-C(=O)-, wherein C(=O) is bound to T;-NRZC-C(=S)-, wherein C(=S) is bound to T;-N=C(S-Rza)-, wherein T is bound to the carbon atom; or -NRzc-C(S-Rza)=, wherein T is bound to the carbon atom;T is O, N or N-RT;R4is aryl, aryl-Ci-C4-alkyl, hetaryl, or hetaryl-Ci-C4-alkyl, wherein the aryl or hetaryl rings are unsubstituted or substituted with one or more R9and wherein the hetaryl is a 5- or 6- membered monocyclic hetaryl or a 8-, 9- or 10-membered bicyclic hetaryl; and whereinRxa, Ryaare, identical or different, H, halogen, Ci-Ce-alkyl, Ci-Ce-alkoxy, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-alkoxy-Ci-C4-alkyl, Cs-Ce-cycloalkyl, Ci-C4-alkyl-C3-C6-cycloalkyl, Ci- C4-alkyl-C3-C6-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;Rxc, Ryc, Rzcare, identical or different, H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, C1-C4- alkyl-Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, Ci-C4-alkyl-C3-C6-cycloalkyl, Ci-C4-alkyl-C3-Ce- cycloalkoxy, or -NRbRc, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;RTis H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-C4-alkyl-Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;Rzais H, Ci-Ce-alkyl, Ci-Ce-alkoxy, C2-Ce-alkenyl, tri-Ci-Ce-alkylsilyl, C2-Ce-alkynyl, C1-C4- alkyl-Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, Ci-C4-alkyl-C3-C6-cycloalkoxy, Ci-C4-alkyl-C3-Ce- cycloalkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, C(=O)-NRbRc, C(=O)-Rd, phenyl, phenylcarbonyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;Rzatogether with RTor Rzcif present, may form a linear Ci-Ce-alkylene or a linear C2-C6- alkenylene group, where in the linear Ci-Ce-alkylene and the linear C2-Ce-alkenylene a CH2 moiety is optionally replaced by a carbonyl and / or wherein 1 or 2 CH2 moieties are optionally replaced by O or S and / or wherein the linear Ci-Ce-alkylene and the linear C2- Cs-alkenylene are unsubstituted or substituted with one or more Rh;155Ra, Rband Rcare, identical or different, H, Ci-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-Ce-alkoxy- Ci-C4-alkyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,Ci-Ce-alkylene-CN, phenyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with one or more Rf;Rdis H, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, phenyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with one or more Rf;Reis Ci-Ce-alkyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, wherein the alkyl, cycloalkyl moieties are unsubstituted or substituted with halogen, phenyl and -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with one or more Rf;Rfis halogen, N3, OH, CN, NO2, -SON, -SF5, Ci-Ce-alkyl, Ci-Ce-alkoxy, C2-Ce-alkenyl, tri-Ci- Ce-alkylsilyl, C2-Ce-alkynyl, Ci-Ce-alkoxy-Ci-C4-alkyl, Ci-Ce-alkoxy-Ci-C4-alkoxy, C3-C6- cycloalkyl, Cs-Ce-cycloalkoxy, C3-Ce-cycloalkyl-Ci-C4-alkyl, C3-Ce-cycloalkoxyx-Ci-C4- alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;R9is halogen, N3, OH, CN, NO2, -SCN, -SF5, Ci-Ce-alkyl, Ci-Ce-alkoxy, 02-Ce-alkenyl, tri-Ci- Ce-alkylsilyl, 02-Ce-alkynyl, Ci-Ce-alkoxy-Ci-C4-alkyl, Ci-C4-alkyl-Ci-Ce-alkoxy, Ci-Ce- alkoxy-Ci-C4-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-cycloalkoxy, C3-Ce-cycloalkyl-Ci-C4-alkyl, C3- Ce-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,C(=O)-ORa, NRbRc, Ci-C6-alkylene-NRbRc, O-Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, NH-Ci-C6-alkylene-NRbRc, C(=O)-NRbRc, C(=O)-Rd, SO2NRbRc, or S(=O)mRe;Rhis halogen, OH, Ci-Ce-alkyl, Cs-Ce-cycloalkyl, or CN; and the N-oxides, stereoisomers, tautomers, and agriculturally or veterinarily acceptable salts thereof.

2. The compound of claim 1 , wherein CRB1and / or CRB2are CH.

3. The compound of claim 1 or 2, wherein R2is phenyl substituted with RArand R3is H or methyl, preferably methyl.

4. The compound of claim 1 or 2, wherein R3is phenyl substituted with RArand R2is H.1565. The compound of any one of claims 1 to 4, wherein R3is selected from the formulae Ar-1 to Ar- 24 and R2is H or R2is selected from the formulae Ar-1 to Ar-24 and R3is H or methyl, preferably methyl:240902W001 B 19223 WO240902EP011586. The compound of any one of claims 1 to 5, wherein(1) X is a single bond, Y is -CRya=N-, wherein the N is bound to Z, Z is -N=C(S-Rza)-, wherein T is bound to the carbon atom, and T is N-RT, wherein Rzatogether with RTforms a linear Ci-Ce-alkylene group, preferably C2 alkylene group, where in the linear Ci-Ce-alkylene a CH2 moiety is replaced by a carbonyl and wherein the linear Ci-Ce-alkylene is unsubstituted or substituted with Rh, and Ryais preferably H; or(2) X is a single bond, Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is -N=C(S-Rza)-, wherein T is bound to the carbon atom, and T is N-RT, wherein Rzatogether with RTforms a linear Ci-Ce-alkylene group, preferably C2 alkylene group, where in the linear Ci-Ce-alkylene a CH2 moiety is replaced by a carbonyl and wherein the linear Ci-Ce-alkylene is unsubstituted or substituted with Rh, and Rycis preferably H; or(3) X is -(C(Rxa)2)P-, wherein p is 2, Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is - N=C(S-Rza)-, wherein T is bound to the carbon atom, and T is N-RT, wherein Rzatogether with RTforms a linear Ci-Ce-alkylene group, preferably C2 alkylene group, where in the linear Ci-Ce-alkylene a CH2 moiety is replaced by a carbonyl and wherein the linear Ci-Ce-alkylene is unsubstituted or substituted with Rh, and all Rxaand Rycare preferably; or(4) X is -(C(Rxa)2)o-NRxc-, wherein 0 is 1 and N is bound to Y, Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is -N=C(S-Rza)-, wherein T is bound to the carbon atom, and T is N-RT, wherein Rzatogether with RTforms a linear Ci-Ce-alkylene group, preferably C2 alkylene group, where in the linear Ci-Ce-alkylene a CH2 moiety is replaced by a carbonyl and wherein the linear Ci-Ce-alkylene is unsubstituted or substituted with Rh, and one Rxa, Rxcand Rycare preferably H and the other Rxais preferably methyl; or(5) X is -(C(Rxa)2)o-NRxc-, wherein 0 is 1 and N is bound to Y, Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is -NRZC-C(=S)-, wherein C(=S) is bound to T, and T is N-RT, wherein one Rxa, Rxc, Ryc, Rzcand RTare preferably H and the other Rxais preferably methyl;(6) X is -(C(Rxa)2)P-, wherein p is 1 , Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is - NRZC-C(=S)-, wherein C(=S) is bound to T, and T is N-RT, wherein one Rxa, Rzcand RTare preferably H, the other Rxais preferably methyl, and Rycis preferably -NH2;(7) X is X is -(C(Rxa)2)o-NRxc-, wherein 0 is 1 and N is bound to Y, Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is -NRZC-C(=S)-, wherein C(=S) is bound to T, and T is N-RT, wherein one Rxa, Ryc, Rzcand RTare preferably H and the other Rxaand Rxcare preferably methyl; or(8) X is -(C(Rxa)2)o-NRxc-, wherein 0 is 1 and N is bound to Y, Y is -NRyc-C(=O)-, wherein C(=O) is bound to Z, Z is -N=C(S-Rza)-, wherein T is bound to the carbon atom, and T is N-RT, wherein Rzatogether with RTforms a linear Ci-Ce-alkylene group, preferably C2 alkylene group, where in the linear Ci-Ce-alkylene a CH2 moiety is replaced by a carbonyl and wherein the linear Ci-Ce-alkylene is unsubstituted or substituted with Rh, and one Rxaand Rycare preferably H and the other Rxaand Rxcare preferably methyl.240902EP011597. The compound of any one of claims 1 to 6, wherein R4is monocyclic or bicyclic aryl substituted with one or more R9, preferably phenyl, naphthyl, or pyridinyl optionally substituted with one or more R9.

8. The compound of any one of claims 1 to 7, wherein R4is selected from the following groups:240902EP011609. The compound of any one of claims 1 to 8, wherein R1is selected from the following groups:240902EP01161 wherein # indicates the point of attachment and wherein R4is preferably R4-29 or R4-31 .

10. The compound of any one of claims 1 to 9, wherein the compound is selected from the following:240902EP01162240902EP01163240902EP01164240902EP01165240902EP01166240902EP01167240902EP01168240902EP01169240902EP01170240902EP01171240902EP01172240902EP01173240902EP01174240902EP01175240902EP01176240902EP01177 and the N-oxides, stereoisomers, tautomers, and agriculturally or veterinarily acceptable salts thereof.

11. A composition, comprising at least one compound of formula I according to any of claims 1 to 10 and any one of a further active substance, an excipient or solvent.

12. 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 according to any of claims 1 to 10 or the composition according to claim 11.

13. A method for protecting growing plants or an animal from attack or infestation by invertebrate pests, which method comprises contacting a plant, or soil or water wherein the plant is growing, or an animal with a pesticidally effective amount of at least one compound according to any of claims 1 to 10 or the composition according to claim 11.

14. Seed comprising a compound according to any of claims 1 to 10 or a composition according to claim 11 , in an amount of from 0.1 g to 10 kg per 100 kg of seed.

15. Use of a compound of the formula I according to any of claims 1 to 10 or of the compositions according to claim 11 , for protecting growing plants from attack or infestation by invertebrate pests.

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