wherein

R ^1a , R ^1b are independently H, halogen, halomethyl, or Ci-C4-alkyl;

R ^1c , R ^1d are independently H, or Ci-C ₄ -alkyl;

R ^2a is halogen, halomethyl, or halomethoxy;

R ^2b , R ^2c are independently H, or as defined for R ^2a ;

Z ¹ ,Z ² ,Z ³ ,Z ⁴ are independently C-R ³ , or N;

R ³ H, halogen, CN, N0 ₂ , OH, N(R ³ )R ³² , Ci-C ₆ -alkyl, C ₃ -C ₇ -cycloalkyl, C ₂ -C ₆ -alkenyl, C3-C7-cycloalkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-haloalkyl, C3-C7- halocycloalkyi, C2-C6-haloalkenyl, C3-C7-halocycloalkenyl, Ci-C6-haloalkoxy, S(0) _m -

Ci-C6-alkyl, or S(0) _m -Ci-C6-haloalkyl, in which aliphatic groups are unsubstituted, partially or fully substituted with one or more R ^a ;

R ³¹ is H, or d-Ce-alkyl,

R ³² is H, Ci-Ce-alkyl, Ci-C ₆ -haloalkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ - alkynyl, C ₂ -C6-haloalkynyl, or C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6- cycloalkylmethyl, or C3-C6-halocycloalkylmethyl which rings are unsubstituted or substituted with a CN;

R ^a is CN, N ₃ , N0 ₂ , SCN, SF ₅ , Si(Ci-C ₄ -alkyl) ₃ , OR ³³ , OS0 ₂ R ³³ , S(0) _n R ³³ ,

N(R ³ )R ³² , C(=0)N(R ³ )R ³² , C(=S)N(R ³ )R ³² , C(=0)OR ³³ , CH=NOR ³³ , C ₃ -C ₈ - cycloalkyl, Cs-Cs-halocycloalkyl, which cyclic moieties may be substituted with

R ³⁴ ; phenyl which is unsubstituted or substituted with one or more R ^A ; and 3- to 7-membered saturated, partially or fully unsaturated heterocycle comprising 1 , 2 or 3 heteroatoms O, N(0) _n or S(0) _m as ring members, which heterocycle is unsubstituted or substituted with one or more R ^A ,

R ³³ H, Ci-Ce-alkyl, Ci-C ₆ -haloalkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, CH ₂ -CN,

C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkylmethyl, C3-C6- halocycloalkylmethyl, phenyl and hetaryl which aromatic rings are unsubstituted or partially or fully substituted with R ^A ;

R ³⁴ is independently OH, CN, Ci-C ₆ -alkoxy, Ci-C ₆ -haloalkoxy, S(0) _m -Ci-C ₆ - alkyl, S(0) _m -Ci-C ₆ -haloalkyl, C(=0)N(R ³ )R ³² , C ₃ -C ₆ -cycloalkyl, or C ₃ -C ₆ - halocycloalkyl which cycles are unsubstituted or substituted with one or more R ³⁴⁴ ; or

phenyl, partially or fully unsaturated heterocycle which rings are unsubstituted or substituted with one or more R ^A ; R ³⁴⁴ is independently OH, CN, Ci-C ₂ -alkyl, or Ci-C ₂ -haloalkyl;

is phenyl or a five- or sixmembered hetaryl comprising up to 4 heteroatoms N(0) _n , O, and S(0)m as ring members, wherein the carbon ring members in Q are unsubstituted or substituted with R ⁴ , nitrogen ring members are unsubstituted or substituted with R ^N ;

T ,T ² are C or N;

m is 0, 1 , or 2;

n is 0, or 1 ;

R ⁴ is independently H, halogen, CN, N0 ₂ , OH, N(R ³ )R ³² , Ci-Ce-alkyl, C ₃ -C ₇ -cycloalkyl, C2-C6-alkenyl, C3-C7-cycloalkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-haloalkyl, C3- C7-halocycloalkyl, C2-C6-haloalkenyl, C3-C7-halocycloalkenyl, Ci-C6-haloalkoxy, S(0) _m -Ci-C ₆ -alkyl, or S(0) _m -Ci-C ₆ -haloalkyl, C(=0)R ³³ , C(=0)OR ³³ , C(=0)N(R ³ )R ³² , in which aliphatic groups are unsubstituted, partially or fully substituted with one or more R ^a ;

R ^N is independently H, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C ₂ -C ₄ -alkynyl, C ₂ -C ₄ -haloalkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -halocycloalkyl, C(=0)R ³³ , C(=0)OR ³³ , C(=0)N(R ³¹ )R ³² ; or phenyl, which is unsubstituted or substittued with halogen, CN, Ci-C4-alkyl or Ci-C2-haloalkyl;

R ³¹ is H, or Ci-Ce-alkyl,

R ³² is H, Ci-Ce-alkyl, Ci-C ₆ -haloalkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ - alkynyl, C2-C6-haloalkynyl, or C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6- cycloalkylmethyl, or C3-C6-halocycloalkylmethyl which rings are unsubstituted or substituted with a CN;

R ³³ H, Ci-Ce-alkyl, Ci-C ₆ -haloalkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, CH ₂ -CN, C ₃ -C ₆ - cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkylmethyl, C3-C6-halocyclo- alkylmethyl, phenyl and hetaryl which aromatic rings are unsubstituted or partially or fully substituted with R ^a ;

R ^a is independently halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cyc- loalkyl, C3-C6-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, S(0) _m -Ci-C4-al- kyl, S(0)m-Ci-C ₄ -haloalkyl;

is A1 : -C(=U)NR ⁵ R ⁶ , or

A2: -(CH ₂ ) _n NR ⁵ C(=U)R ⁶ ; wherein

U is O, or S; and

R ⁵ is H, OH, C(=0)R ³¹ , C(=0)OR ³¹ , CN, Ci-Ce-alkyl, Ci-C ₆ -alkoxy, C ₂ -C ₄ -alkenyl, C ₂ - C ₄ -alkynyl, C ₃ -C ₈ -cycloalkyl, C ₂ -Cio-alkenyl, C ₂ -Cio-alkynyl, N(R ³¹ )R ³² , phenyl or saturated, partially or fully unsaturated heterocycle, which groups are unsubstituted or substituted with one or more R ^a ; and wherein the rings are bonded directly or via Ci-C4-alkyl spacer;

R ⁶ is H, Ci-Ce-alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkyl-Ci- C4-alkyl, Ci-C6-alkylcarbonyl, Ci-C6-alkoxycarbonyl, phenyl or saturated, partially or fully unsaturated heterocycle, which groups are unsubstituted or substituted with one or more R ^aa ; and wherein the rings are bonded directly or via Ci-C4-alkyl spacer; R ^aa is halogen, CN, Ci-C ₆ -alkyl, OR ³¹ , C(=NOR ⁵¹ )R ⁵² ; C(=0)N(R ³ )R ³² ,

C(=S)N(R ³¹ )R ³² , or C(=0)OR ³¹ ; or two R ^aa bound to the same C-atom form together C3-C6-cycloalkyl;

R ⁵¹ ,R ⁵² are independently H, d-C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₃ - Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, phenyl or saturated, partially or fully unsaturated heterocycle, which groups are unsubstituted or substituted with one or more halogen, CN, NO2; and wherein the rings are bonded directly or via Ci-C4-alkyl spacer;

and the N-oxides, stereoisomers and agriculturally or veterinarily acceptable salts thereof.

The invention also provides an agricultural composition comprising at least one compound of formula I, a stereoisomer thereof and/or an agriculturally acceptable salt thereof and at least one liquid and/or solid carrier, especially at least one inert liquid and/or solid agriculturally acceptable carrier.

The invention also provides a veterinary composition comprising at least one compound of formula I, a stereoisomer thereof and/or a veterinarily acceptable salt thereof and at least one liquid and/or solid carrier, especially at least one inert veterinarily liquid and/or solid acceptable carrier.

The invention also provides a method for controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a cultivated plant, plant propagation materials (such as seed), soil, area, material or environment in which the pests are growing or may grow, or the materials, cultivated plants, plant propagation materials (such as seed), soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a compound of formula I or a salt thereof as defined herein. The present invention also relates to plant propagation material, in particular seed, comprising at least one compound of formula I and/or an agriculturally acceptable salt thereof.

The invention further relates to a method for treating or protecting an animal from infestation or infection by parasites which comprises bringing the animal in contact with a parasiticidally effective amount of a compound of formula I or a veterinarily acceptable salt thereof. Bringing the animal in contact with the compound I, its salt or the veterinary composition of the invention means applying or administering it to the animal.

WO 2016/168059 and WO 2017/055414 describe structurally closely related active compounds. These compounds are mentioned to be useful for combating invertebrate pests. Nevertheless, there remains a need for highly effective and versatile agents for combating invertebrate pests. It is therefore an object of the present invention to provide compounds having a good pesticidal activity and showing a broad activity spectrum against a large number of different invertebrate pests, especially against difficult to control pests, such as insects.

It has been found that these objects can be achieved by compounds of formula I as depicted and defined below, and by their stereoisomers, salts, tautomers and N-oxides, in particular their agriculturally acceptable salts.

Compounds of formula I can be prepared by the methods as described in the below schemes, or in the synthesis descriptions of the working examples, or by standard methods of organic chemistry which are known to a person skilled in the art. The substituents, variables and indices are as defined above for formula I, if not otherwise specified. Depending on the selection of variables it may be advantageous to change the order of the reaction steps. Compounds of formula I, wherein A = A1 and U = O (formula 1.1 ) can be prepared by ami- dation of an acid of formula 11.1 with amines of formula Xa.

This transformation is usually carried out at temperatures of from -10°C to 120°C, preferably from 0°C to 35°C, in an inert solvent, in the presence of a base and an activator [cf. Ngo, Thien H. et al, Journal of Organic Chemistry, 77(21 ), 9676-9683; 2012].

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and petrol ether, aromatic hydrocarbons such as toluene, o-, m-, and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform, and chlorobenzene, ethers such as diethylether, diisopropylether, tert.-butylmethylether (MTBE), dioxane, anisole, and tetrahydrofurane (THF), nitrils such as acetonitrile, and propionitrile, moreover dimethyl sulphoxide (DMSO), dimethyl formamide (DMF), and dimethylacetamide (DMA), preferably aromatic hydrocarbons such as toluene, o-, m-, and p-xylene, halogenated hydrocarbons such as methylene chloride and chlorobenzene. It is also possible to use mixtures of the solvents mentioned.

Suitable coupling reagents (activators) are known and are, e.g. selected from carbodiimides, such as Ν,Ν-dicyclohexylcarbodiimide ("DCC") and Ν,Ν-diisopropylcarbodiimide ("DCI"), benzo- triazole derivatives such as 1 -[bis(dimethylamino)methylene]-1 H-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate ("HATU"), 0-(benzotriazol-1 -yl)-N,N,N',N'-tetramethyluronium hex- afluorophosphate ("HBTU"), and 1 -[bis(dimethylamino)methylen]-5-chlorobenzotriazolium 3-ox- ide hexafluorophosphate ("HCTU"), or phosphonium-derived activators, such as (Benzotriazol- 1 -yloxy)tris(dimethylamino)phosphonium hexafluorophosphate ("BOP"), (benzotriazol-1 -yl-oxy- tripyrrolidinophosphonium hexafluorophosphate) ("Py-BOP"), bromotripyrrolidinophosphonium hexafluorophosphate ("Py-BrOP). Generally, the activator is used in excess. The benzotriazole and phosphonium coupling reagents are generally used in a basic medium.

The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ an excess of Xa, based on 11.1.

Amines of formula Xa are commercially available, or can be made as described in literature, or by standard methods of organic chemistry which are known to a person skilled in the art.

Alternatively compounds of formula I, wherein A = A1 and U = O (formula 1.1 ) can be prepared by amidation of an acid chloride of formula II.2 with amines of formula Xa.

This transformation is carried out under conditions generally known in the art, e.g. from WO2004/22536. The transformation is usually carried out at temperatures from -40 °C to 100 °C, preferably from 0 °C to 30 °C.

Suitable solvents are halogenated hydrocarbons such as dichloromethane, chloroform, and chlorobenzene, or polar aprotic solvents such as THF, and DMF, or aromatic hydrocarbons such as benzene, toluene, o-, m-, and p-xylene, or mixtures thereof.

The reaction is generally carried out in the presence of an organic base such as triethylamine (NEt.3), Ν,Ν-diisopropylethylamine (iP^NEt), pyridine, substituted pyridines such as collidine or lutidine. Optionally a nucleophilic catalyst such as 4-(N,N-dimethylamino)pyridine ("DMAP") can be employed in the reaction.

The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ an excess of Xa, based on II.2. The acid chlorides II.2 can be prepared by reacting acids of formula 11.1 with thionylchloride or oxalyl chloride.

This transformation is carried out under conditions generally known in the art, e.g. dissolving the compound in e.g. thionylchloride or oxalyl chloride. The reaction may proceed at room tem- perature (r.t.; 20-25°C) or at elevated temperatures, such as from 35 to 90°C.

The acids 11.1 can be prepared by saponification of esters of type III.1 with R being small alkyl like CHs

The saponification is carried out under conditions generally known in the art, e.g. dissolving the compound III.1 in either THF, methanol or water or a mixture of the solvents, and adding alkali metal hydroxides, such as LiOH, NaOH, and KOH either as solid or in solution to the mixture. The reaction may proceed at r.t. or elevated temperatures. Workup in a customary manner by aqueous extraction typically yields the title compound [cf. WO2013/032804]. Alternatively, acids of formula 11.1 can be prepared by subjecting a compound of formula 111.2, wherein X is Br or I, to a halogen-metal exchange followed by the in situ reaction of this metal- lated intermediate with carbon dioxide. Suitable reaction conditions are described in the literature, e.g. in WO2009/132000, EP1582523.

Suitable metalating agents are, e.g. iP^MgCI, iPr2MgCI-LiCI ("TurboGrignard"), n-butyllithium, tert-butyllithium. Optionally, the reaction can be performed in the presence of an additional amine ligand such as, e.g., Ν,Ν,Ν',Ν'-tetramethylethylenediamine ("TMEDA"). Suitable solvents are ethers such as THF, 2-methyltetrahydrofurane, diethyl ether (Et.20), or aliphatic hydrocar- bons such as pentane, hexane, cyclohexane, or mixtures thereof.

The esters 111.1 can be obtained by reacting a compound of formula III.2, wherein X is halogen or OS(=0)2CF3 ("OTf"), with carbon monoxide in the presence of a palladium catalyst and an alcohol ROH, wherein R is Ci-Cs-alkyl. Suitable reaction conditions are described in literature (c

Compounds of formula I, wherein A = A1 and U = S (= formula 1.2) can be prepared by reacting compounds of formula 1.1 with a sulfur containing reagent.

The transformation is preferably done by using a reagent of type Xb in polar solvents such as acetonitrile, acetone, THF, DMF, or in an inert solvent such as dichloromethane, 1 ,2-dichloro- ethane, or 1 ,2-dimethoxyethane at temperatures from r.t. to the reflux temperature of the solvent. Suitable R ^a groups for Xb are: thio, alkyl, aryl or substituted aryl. Representative reaction conditions for thionation of analogous substrates are given in European Journal of Organic Chemistry, 2000, 3273-3278.

Compounds of formula I, wherein A = A2, U = O, and n=0 or 1 (formula 1.3) can be prepared by amidation of an amine II.3 with acids (X = OH) or acid chlorides (X = CI) of formula Xc. The corresponding thioamides 1.4 can be prepared by reacting an amide of formula 1.3 with a sulfur containing reagent.

This amidation is analogously done as described for the reaction of 11.1 to 1.1 or I I .2 to 1.1 . Acids or acid chlorides of formula Xc are commercially available, or can be made as described in literature, or by standard methods of organic chemistry which are known to a person skilled in the art. The thioamides can be prepared analogous as described for the reaction of 1.1 to 1.2.

Alternatively compounds of formula I , wherein A = A2, U = O, and n = 1 (formula 1.3) can be prepared by reductive amidation of a nitrile 11.4 in the presence of hydrogen and an activated carbonyl compound of formula Xc wherein X is a nucleophilic leaving group such as halogen or

This transformation is usually carried out at temperatures of from -50°C to 150°C, preferably from -10°C to 50°C, in an inert solvent, in the presence of a base and a catalyst [cf. J. Org. Chem. 1988, 53, 2847].

Suitable solvents are aliphatic hydrocarbons, aromatic hydrocarbons such as toluene, o-, m-, and p-xylene, ethers such as diethylether, Diisopropylether, MTBE, dioxane, anisole, and THF, esters such as ethyl acetate, methyl acetate, isopropyl acetate, alcohols such as methanol, eth- anol, n-propanol, isopropanol, n-butanol, and tert.-butanol, moreover DMF, and DMA, acids such as acetic acid, and water, preferably ethers and alcohols. It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as LiOH, NaOH, KOH and Ca(OH)2, alkali metal and alkaline earth metal carbonates, such as U2CO3, Na2C03, K2CO3 and CaC03, and also alkali metal bicar- bonates, such as NaHC03, KHCO3, moreover organic bases, e.g. tertiary amines, such as tri- methylamine (NMe3), NEt.3, iP^NEt and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to alkali metal bicarbonates and carbonates, such as NaHC03, or KHCO3. The bases are generally employed in catalytic amounts; however, they can also be used in equimolar amounts, in excess or, if appropriate, as solvent.

The reaction step can only be performed in the presence of a hydrogenation catalyst. As used herein, the term "hydrogenation catalyst" covers heterogeneous and homogeneous hydrogenation catalysts, but preferably refers to heterogeneous catalysts. It is known in the art that platinum, palladium, rhodium, and ruthenium form highly active catalysts. Non-precious metal catalysts, such as catalysts based on nickel, such as Raney nickel and Urushibara nickel, are eco- nomical alternatives. In a preferred embodiment, the hydrogenation catalyst is selected from the group consisting of platinum or palladium on a carrier, Raney nickel, and Raney cobalt. Raney nickel is particularly preferred.

This reaction is carried out in the presence of hydrogen or a hydrogen source, preferably hydrogen is used. The reaction is in general carried out under atmospheric pressure, which usu- ally is in the range from 0.1 to 10 bar, preferably in the range of from 0.1 to 1 bar.

The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ an excess of Xc, based on II.4.

Compounds of formula IV.1 , wherein A ^x is A (formula 1.1 , 1.2, 1.3, 1.4) or any precursor of A, e.g. COOH, COOR, (CH ₂ )nNH ₂ , CN (formula 11.1 , III.1 , II.3, II.4) can be prepared by cross coupling of compounds of type IV.2 with IV.3 in the presence of a metal catalyst, wherein Xi is a leaving group like halogen or OTf and X2 is a metal species like a tin species, zinc species, silates or boron species. In another preferred embodiment Xi is a metal species like a tin species, zinc species, silates or boron species and X2 is a leaving group like halogen or OTf. Suitable re- action condtions are described in literature, e.g. in de Meijere et. al., "Metal-Catalyzed Cross-

literature, or by standard methods of organic chemistry which are known to a person skilled in the art.

Compounds of formula IV.2 can be prepared by cyclopropanation of compounds of formula

IV.4.

In cases, where R ^1a and R ^1b are CI or Br, compounds of formula IV.4 can undergo a cyclopropanation in the presence of a base such as NaOH and in the presence of a carbene source such as chloroform or bromoform and a phase transfer catalyst as described in

WO2016168059. Suitable solvents are polar protic solvents such as water. This transformation is usually carried out at temperatures of from 0°C to 40°C.

Alternatively, in cases, where R ^1a and R ^1b are both CI, compounds of formula IV.4 can undergo a cyclopropanation with bromo(dichloro)methyltrimethylsilane (TMSCC Br) to yield the dichloro- cyclopropyl compounds IV.2 (R ^1a and R ^1b are CI).

This transformation is usually carried out at temperatures of from -100°C to 50°C, preferably from -78°C to 30°C, in an inert solvent, in the presence of a base [cf. Lee et al, Chem. Eur. J. 2016, 22, 7609-16].

Suitable solvents are halogenated hydrocarbons, ethers such as dioxane, anisole, and THF, nitrils such as acetonitrile, and propionitrile, moreover DMSO, DMF, and DMA, preferably THF, acetonitrile, and DMF. It is also possible to use mixtures of the solvents mentioned. Suitable bases are, in general, organic bases, preferably ammonium salts such as tetrabutylammonium fluorides, preferably NBu ₄ F, and NBu ₄ PhsSiF2. The bases are generally employed in equimolar amounts; however, they can also be used in small excess. Alternatively, compounds of formula Va, that are compounds of formula IV.1 , or IV.2 wherein Z ¹ and Z ² are N, Z ³ and Z ⁴ are CR ³ , and Y1 is an arene Q, substituted with A ^x (i.e. IV.1 ), or X1 (i.e. IV.2), can be obtained by reacting an amidine of formula VI.2 with a compound of formula Xd, or Xe, respectively. Suitable reaction conditions are described in the literature, for example in WO2012/80052.

The reaction is generally carried out in the presence of a base. Suitable bases are e.g. alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, or alkali and alkaline earth metal hydroxides, such as LiOH, NaOH, KOH, Ca(OH)2, or alkali metal and alkaline earth metal carbonates, such as L12CO3, Na2C03, K2CO3 and CaCO-3, or alkali metal carboxylates such as sodium acetate, or organic amine bases such as NEt.3, iP^NEt, 1 ,8-di- azabicyclo[5.4.0]undec-7-ene. Suitable solvents are alcohols such as methanol, ethanol, n-pro- panol, isopropanol, n-butanol, tert-butanol, or polar aprotic solvents such as DMF, acetonitrile, 1 ,4-dioxane, DMSO, or water. It is also possible to use mixtures of the solvents mentioned. Compounds of formula Xd, and Xe are commercially available or can be prepared as de- scribed in literature, or by standard methods which are known to a person skilled in the art.

Compounds of formula Va', that is compounds of fomula Va, wherein Z ³ , Z ⁴ are CH, can be obtained by reacting an amidine of formula VI.2 with an enal of formula Xf, wherein LG denotes a leaving group such as, for example, ΝΜβ2, OR, or halogen, in a Michael-addition/condensation reaction. Suitable reaction conditions are similar as described above for the synthesis of compounds of formula Va and can be found in the literature, for example in WO2010/141273. Compounds of formula Xf are commercially available or can be prepared as described in literature, or by standard methods which are known to a person skilled in the art.

In turn, amidines of formula VI.2 can be obtained by reacting an ester of formula VI.1 b with ammonia or an ammonium salt, preferably NH4CI, in an amidation reaction. Suitable reaction conditions are described in the literature, e.g. in WO2014/202583.

The reaction is usually carried out in the presence of a Lewis acid promotor, preferably tri- methylaluminum. Suitable solvents are, e.g. aliphatic hydrocarbons such as pentane, hexane, heptane, cyclohexane, petrol ether, or aromatic hydrocarbons such as toluene, 0-, m-, p-xylene, or halogenated hydrocarbons such as methylene chloride, chloroform, chlorobenzene. It is also possible to use mixtures of the solvents mentioned. The reaction is usually performed at initial temperatures from -50 °C to 50 °C, preferably from 0 °C to 30 °C, and then in a second stage at temperatures from 20 °C to 180 °C, preferably from 80 °C to 120 °C. Esters of formula VI.1 b are known from WO2016/168059, and US6887870. Compounds of formula Vb, that is compounds of formula IV.1 , or IV.2 wherein Z ¹ and Z ² are CR ³ , Z ³ and Z ⁴ are N, and Y1 is an arene Q, substituted with A ^x (i.e. IV.1 ), or X1 (i.e. IV.2), can be obtained by reacting an alpha, beta-unsaturated carbonyl compound of formula VI.3 with an amidine of formula Xg in a Michael-addition/condensation reaction, analoguously as described above for the preparation of compounds of formula Va. Compounds of formula Xg are commer- cially available or can be prepared from the corresponding esters, analoguously as described above for compounds of formula VI.2.

In turn, compounds of formula VI.3 can be accessed by reacting a vinyl iodide of formula VI.4 with an organometallic species of formula Xh, wherein M is e.g. Li, MgX (X = CI, Br, I, or R ³ ), ZnX (X = CI, Br, I, or R ³ ), Cu, BR2, SnR3, and the like, in the presence of a palladium catalyst and a carbon monoxide atmosphere in a Carbonylative Cross-Coupling reaction. Suitable reaction conditions are described in literature, e.g. in W. F. Goure et al. Journal of the American Chemical Society, 1984, 106, 6417-6422, or in de Meijere et. al., "Metal-Catalyzed Cross-Coupling Reactions and More", Wiley-VCH, 2014. Compounds of formula Xh are commercially available or can be prepared as described in literature, or by standard methods which are known to a person skilled in the art.

Alternatively, compounds of formula VI.3 can be prepared by reacting a vinyl iodide of formula VI.4 with an alkyl vinyl ether of formula Xi in a Heck-Reaction, followed by aqueous acid mediated hydrolysis of the obtained enol ether. Suitable reaction conditions are described in the liter- ature, for example in WO2014/206907. The reaction is generally carried out in the presence of a palladium catalyst such as Pd(OAc)2/tris(o-tolyl)phosphine, bis(triphenylphosphine)palladium(ll) dichloride, tetrakis(triphenylphosphine)palladium(0), [1 ,1 '-Bis(di-tert-butylphosphino)ferrocene]- dichloropalladium(ll), Pd(tBu3P)2, and in the presence of a base such as an amine base like NEt.3, iPr2NEt, N-methyl-N,N-dicyclohexylamine, or an alkali metal carbonate such as Na2C03, K2CO3, CS2CO3. Suitable solvents are polar aprotic solvents such as DMF, DMA, acetonitrile, THF, or aromatic hydrocarbons such as toluene, 0-, m-, and p-xylene, or mixtures thereof. Alkyl vinyl ethers of formula Xi are commercially available or can be prepared as described in literature, or by standard methods which are known to a person skilled in the art.

Furthermore, compounds of formula VI.3 can also be prepared by subjecting vinyl iodides of formula VI.4 to a halogen-metal exchange followed by the in situ reaction of this metallated intermediate with an amide of formula Xj, preferably a Weinreb amide, wherein R2N is

N(Me)OMe. Suitable reaction conditions are described in the literature, for example in G. Sorin et al. Organic Letters, 2013, 15, 4734-4737. Suitable metalating agents are, e.g. iPr ₂ MgCI, iPr2MgCI-LiCI ("TurboGrignard"), n-butyllithium, tert-butyllithium. Optionally, the reaction can be performed in the presence of an additional amine ligand such as, e.g., Ν,Ν,Ν',Ν'-tetramethyleth- ylenediamine. Suitable solvents are ethers such as, e.g., THF, 2-methyltetrahydrofurane, diethyl ether (Et.20), or aliphatic hydrocarbons such as pentane, hexane, cyclohexane, or mixtures thereof. Amides of formula Xj are commercially available or can be prepared as described in lit- erat

Vinyl iodides of formula VI.4, can be prepared by reacting a hydrazone of formula VI.5 with iodine in the presence of a base. Suitable reaction conditions are described in the literature, for example in D. H. R. Barton et al. Tetrahedron Lett. 1983, 24, 1605-1608. Suitable bases are, e.g. tertiary amine bases such as NEt.3, iP^NEt, 1 ,4-diaza-bicyclo[2.2.2]octane, or amidine bases such as 1 ,8-diazabicyclo[5.4.0]undec-7-ene, and the like, or guanidine bases such as guan- idine, Ν,Ν,Ν',Ν'-tetramethylguanidine, 2-(tert-butyl)-1 ,1 ,3,3-tetramethylguanidine. Suitable solvents are ethers such as THF, Et^O, 1 ,4-dioxane, or halogenated hydrocarbons such as di- chloromethane, chloroform, 1 ,2-dichloroethane, chlorobenzene, or aromatic hydrocarbons such as benzene, toluene, 0-, m-, and p-xylene, and the like. It is also possible to use mixtures of the solvents mentioned.

Hydrazones of formula VI.5 can be prepared by reacting a ketone of formula VI.6 with hydra- zine in a condensation reaction. Suitable reaction conditions are described in literature, e.g. D. J. Tao et al., JACS 2016, 138, 2186-2189. Preferably, hydrazine is employed as the corresponding hydrate. Suitable solvents are, e.g., alcohols such as methanol, ethanol, n-butanol, isopropanol, tert-butanol, or polar aprotic solvents such as THF, 1 ,4-dioxane, DMF, DMSO, or aromatic hydrocarbons such as benzene, toluene, 0-, m-, and p-xylene. It is also possible to use mixtures of the solvents mentioned. Optionally, an acid can be employed in the reaction, e.g. a carboxylic acid such as acetic acid, or a mineral acid such as H2SO4, HCI, HBr, or a sulfonic acid such as para-toluenesulfonic acid. Alternatively, it is also possible to employ a base in the reaction, e.g. a tertiary amine base such as NEt.3, iP^NEt. The reaction is usually performed at temperatures from 20 °C to 180 °C, preferably from 20°C to 100°C. Hydrazine is usually used in a slight excess based on VI.6, however, it can also be used in large excess. The acids or bases are preferably employed in catalytic amounts; however, they can also be used in equimolar amounts, in excess or, if appropriate, as solvent.

Ketones of formula VI.6 can be prepared by reacting a Weinreb amide of formula VI.7 with the corresponding organolithium or organomagnesium compound of formula M-Z ² H2, wherein M is Li, or MgX (X = CI, Br, I), in a Weinreb Ketone Synthesis reaction. Suitable reaction conditions are described in literature (cf. US6887870, EP2746260). Suitable solvents are ethers such as THF, Et.20, diisopropylether, MTBE, or aliphatic hydrocarbons such as pentane, hexane, cyclo- hexane, petrol ether, or mixtures thereof. The transformation is usually carried out at tempera- tures fro °C to 50 °C, preferably from -78 °C to 25 °C.

Weinreb amides of formula VI.7 can be prepared by reacting a carboxylic acid of formula VI.1a, wherein X ^E is OH, or a carboxylic acid derivative of formula VI.1 b, wherein X ^E is a leaving group, preferably a halogen such as CI or Br, or Ci-C6-alkoxy, such as OCH3 or OC2H5, with the Weinreb amine of formula CH3NH(OCH3) in an amidation reaction. Most preferrably, the Weinreb amine is used as its hydrochloride salt (CAS 6638-79-5) and the reaction is carried out with the corresponding esters of formula VI.1 b, in the presence of a Lewis acid such as MesAI, or Me2AICI. Suitable reaction conditions are described in literature (cf. US6887870). Suitable solvents are halogenated hydrocarbons such as dichloromethane, chloroform, and chlorobenzene, or aromatic hydrocarbons such as benzene, toluene, o-, m-, and p-xylene, or polar aprotic solvents such as THF, Et.20, or aliphatic hydrocarbons such as pentane, hexane, cyclohexane, petrol ether, or mixtures thereof. Alternatively, Weinreb amides of formula VI.7 can also be obtained by reacting acyl chlorides of formula VI.1 b or carboxylic acids of formula VI.1a, respectively, with the Weinreb amine CH3NH(OCH3) or its hydrochloride salt under analogous amida- tion reaction conditions a pounds of formula 1.1.

Compounds of formula Vc, that is compounds of formula IV.1 , or IV.2 wherein Z ² is N, Z ¹ , Z ³ and Z ⁴ are CR ³ , and Y1 is an arene Q, substituted with A ^x (i.e. IV.1 ), or X1 (i.e. IV.2), can be obtained by reacting a triazine of formula Ve with an alkyne of formula Xk in a Diels-Alder/retro- Diels-Alder domino reaction [cf. S. Diring et al. J. Org.Chem. 2007, 72, 10181 -10193], or by reacting a triazine of formula Ve with an alkyne surrogate, such as an enamine of formula Xm or Xm', in a Diels-Alder/retro-Diels-Alder/elimination domino reaction [cf. D. L. Boger et al. J. Org. Chem. 1981 , 46, 2179-2182]. If desired, it is also possible to generate the required enamine of formula Xm or Xm' in situ by reacting the corresponding ketone with a secondary amine HNR2 such as pyrrolidine [cf. D. L. Boger et al., JOC 1982, 47, 895-897]. Suitable solvents are halo- genated hydrocarbons such as 1 ,2-dichlorobenzene, chlorobenzene, 1 ,2-dichloroethane, chloroform, dichloromethane, or aromatic hydrocarbons such as 0-, m-, and p-xylene, toluene, benzene, or ethers such as 1 ,4-dioxane, diphenyleher, diethylene glycol dimethyl ether, THF, or polar aprotic solvents such as DMF, DMSO, nitrobenzene. It is also possible to use mixtures of the solvents mentioned. Optionally, molecular sieves can be employed in the reaction, preferably 3- 4A molecular sieves are used. The transformation is usually carried out at temperatures from 40 °C to 250 °C, preferably from 60 °C to 220 °C.

Alternatively, compounds of formula Vc', that is compounds of formula Vc wherein Z ¹ and Z ³ are CH, can be prepared by reacting a triazine of formula Ve with bicyclo[2.2.1 ]hepta-2,5-diene in a Diels-Alder/retro-Diels-Alder/retro-Diels-Alder domino reaction under otherwise analoguous conditions as described above for the synthesis of compounds of formula Vc [cf. M. A. Honey et al. JOC 2012, 77, 1396-1405].

Compounds of formula Vd, that is compounds of formula IV.1 , or IV.2 wherein Z ⁴ is N, Z ¹ , Z ² and Z ³ are CR ³ , and Y1 is an arene Q, substituted with A ^x (i.e. IV.1 ), or X1 (i.e. IV.2), can be obtained by reacting a triazine of formula Vf with an alkyne of formula Xk, or an alkyne surrogate, such as an enamine of formula Xm or Xm', analoguously as described above for the synthesis of compounds of formula Vc.

Compounds of formula Ve, that is compounds of formula IV.1 , or IV.2, wherein Z ¹ , Z ² , and Z ³ are N, Z ⁴ is CR ³ , and Y1 is an arene Q, substituted with A ^x (i.e. IV.1 ), or X1 (i.e. IV.2), can be obtained by reacting a hydrazide of formula VI.8 with compound of formula Xn, wherein X is a halogen, in a condensation-type reaction. Suitable reaction conditions are described in literature (cf. V. N. Kozhevnikov et al., THL 2008, 49, 4096-4098).

The reaction is usually carried out in the presence of a base, e.g. an alkali metal carboxylate such as NaOAc. Suitable solvents are alcohols such as methanol, ethanol, n-propanol, isopro- panol, n-butanol, tert-butanol, or polar aprotic solvents such as DMF, DMSO, 1 ,4-dioxane, or carboxylic acids such as acetic acid. It is also possible to use mixtures of the solvents mentioned. The reaction is usually performed at temperatures from 20 °C to 180 °C, preferably from 40°C to 120°C. Generally, an excess of the hydrazide VI.8 is employed in the reaction, based on Xn, preferably 2 equivalents are used.

In turn, a hydrazide of formula VI.8 can be prepared by reacting a carboxylic acid of formula VI.1a, wherein X ^E is OH, or a carboxylic acid derivative of formula VI.1 b, wherein X ^E is a leaving group, preferably a halogen such as CI or Br, or Ci-C6-alkoxy, such as OCH3 or OC2H5, with hydrazine in an amidation-type reaction.

The amidation-type reaction is preferably carried out with esters of formula VI.1 b and the hydrazine is preferably used in the form of its corresponding hydrate of formula Η2ΝΝΗ2Ή2Ο. Suitable solvents are alcohols such as methanol, ethanol, iso-propanol, tert-butanol, or polar aprotic solvents such as 1 ,4-dioxane, acetonitrile, or water, and mixtures thereof. The transformation is usually carried out at temperatures from 20 °C to 180 °C, preferably from 20 °C to 100 °C. The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ an excess hydrazine, based on VI.1. Alternatively, the amidation-type reaction is can carried out with acid chlorides of formula VI.1 b or by prior transformation of carboxylic acids of formula VI.1a with [(COCI)2] or SOC to the corresponding acid chlorides of formula VI.1 b, followed by reaction with hydrazine. Suitable reaction conditions are described in literature (cf. WO2016/168059, US201 1/195954). The reaction is preferrably carried out in the presence of an organic base such as NEt.3, iP^NEt, pyridine, or substituted pyridines such as collidine or lutidine. Optionally a nucleophilic catalyst such as DMAP can be employed in the reaction. Suitable solvents are halogenated hydrocarbons such as dichloromethane, chloroform, and chlorobenzene, or polar aprotic solvents such as THF, 1 ,4- dioxane, and DMF, or aromatic hydrocarbons such as benzene, toluene, 0-, m-, and p-xylene, or mixtures thereof. The transformation is usually carried out at temperatures from -40 °C to 120 °C, preferably from 0 °C to 40 °C. The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ an excess of the hydrazine, based on VI.1.

Furthermore, the amidation-type reaction of a carboxylic acid of formula VI.1a with hydrazine can also be carried out in the presence of a coupling reagent. Suitable coupling reagents (activators) are known and are, e.g. selected from carbodiimides, such as DCC and DCI, benzotriazole derivatives such as HATU, HBTU, and HCTU, or phosphonium-derived activators, such as BOP, Py-BOP, Py-BrOP. Generally, the activator is used in excess. The benzotriazole and phospho- nium coupling reagents are generally used in a basic medium. Compounds of formula Xn are commercially available or can be prepared as described in literature, or by standard methods which are known to a person skilled in the art.

Alternatively, compounds of formula Ve, that is compounds of formula IV.1 , or IV.2, wherein Z ¹ , Z ² , and Z ³ are N, Z ⁴ is CR ³ , and Y1 is an arene Q, substituted with A ^x (i.e. IV.1 ), or X1 (i.e. IV.2), can be obtained by reacting an amidrazone of formula VI .9 with a compound of formula Xo in a condensation-type reaction. Suitable reaction conditions are described in the literature, for example in US2016/145271.

The reaction is usually performed in the presence of an acid such as a carboxylic acid like acetic acid, ammonium acetate, or a mineral acid such as HCI. Suitable solvents are alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, tert-butanol, or polar aprotic solvents such as DMF, acetonitrile, THF, 1 ,4-dioxane, or carbocylic acids such as acetic acid. It is also possible to use mixtures of the solvents mentioned. The reaction is usually performed at temperatures from 20 °C to 200 °C, preferably from 60°C to 180°C. If desired, amidrazones of formula VI .9 can be generated in situ from hydrazides of formula VI.8 by employing ammonium acetate as the acid in the reaction. Suitable reaction conditions are described in literature (cf. US2007/207985). Otherwise, the amidrazone of formula VI.9 can be prepared in a separate step by reacting an amidine of formula VI.2 with hydrazine, preferably used as its hydrate, as described e.g. in US2016/145271 . Optionally, a base can be employed in the reaction such as an amine base like NEt.3, iP^NEt, piperidine. Suitable solvents are, e.g., alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, tert-butanol, or polar aprotic solvents such as THF, DMF, acetonitrile, 1 ,4-dioxane. It is also possible to use mixtures of the solvents mentioned. The reaction is usually performed at temperatures from 0 °C to 100 °C, preferably from 20°C to 60°C.

Compounds of formula Vf, that is compounds of formula IV.1 , or IV.2, wherein Z ¹ , Z ³ , and Z ⁴ are N, Z ² is CR ³ , and Y1 is an arene Q, substituted with A ^x (i.e. IV.1), or X1 (i.e. IV.2), can be obtained by reacting an alpha-haloketone of formula VI.10, wherein X is a halogen, with a hy- drazide of formula Xp in a condensation-type reaction, analoguously as described above for the preparation of compounds of formula Ve. Compounds of formula Xp are commercially available or can be prepared from the corresponding carboxylic acid, ester, or acyl chloride, analoguously as described above for the synthesis of compounds of formula VI.8.

In turn, alpha-haloketones of formula VI.10, wherein X is CI, Br or I, can be prepared by treating a ketone of formula VI.6 with a halogenating agent in an alpha-halogenation reaction, as shown in the scheme below. Suitable reaction conditions are described in literature (cf.

US2010/19 ).

Suitable halogenating agents are chlorine, bromine, iodine, NCS, N-bromosuccinimide ("NBS"), N-iodosuccinimide, sulfuryl dichloride, phenyltrimethylammonium tribromide, tetraethylammo- nium trichloride, copper(ll)bromide. Optionally, an acid can be employed in the reaction such as a Bronsted acid like acetic acid, HBr, HCI, H2SO4, TsOH, or Lewis acids such as AICI3. Suitable solvents are halogenated hydrocarbons such as dichloromethane, chloroform, 1 ,2-dichloro- ethane, or ethers such as THF, Et.20, TBME, 1 ,4-dioxane, or alcohols such as methanol, ethanol, or ethyl acetate, or acetic acid, or water, or mixtures thereof. Alternatively, the halogenation reaction can also be performed by prior transformation of ketone VI.6 into the corresponding alkali metal enolate using an alkali metal amide base such as LiN[Si(CH3)3]2, LDA, LTMP, followed by its in situ reaction with a halogenating agent such as NCS, NBS, N-iodosuccinimide, TsCI, trifluoromethanesulfonyl chloride, hexachloroethane, chlorine, bromine, iodine. Suitable reaction conditions are described in literature (cf. US6887870). Suitable solvents are ethers such as THF, Et^O, or aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and petrol ether, or mixtures thereof. If desired, it is also possible to intercept the alkali metal enolate with a chlorotrialkylsilane such as chlorotrimethylsilane, chlorotriethylsilane, tert-butyldimethylsi- lyl chloride, to give the corresponding silyl enol ether which can be isolated and treated with a suitable halogenating agent in a separate step. Suitable halogenating agents are chlorine, bromine, iodine, NCS, NBS, N-iodosuccinimide, sulfuryl dichloride, phenyltrimethylammonium tri- bromide, tetraethylammonium trichloride. Suitable reaction conditions are described in literature (cf. WO2017/005786).

Compounds of formula Vg, that is compounds of formula IV.1 , or IV.2 wherein Z ² and Z ⁴ are N, Z ¹ and Z ³ are CR ³ , and Y1 is an arene Q, substituted with A ^x (i.e. IV.1 ), or X1 (i.e. IV.2), can be obtained by reacting a triazine of formula Vh with an alkyne of formula Xk [cf. M. D. Helm et al. Angew. Chem. Int. Ed, 2005 44, 3889-3892], with an alkyne surrogate such as an enamine of formula Xm or Xm' [cf. H. Xie et al. Org. Lett. 2008, 10, 1923-1926], or with bicyclo[2.2.1 ]hepta- 2,5-diene, analoguously as described above for the synthesis of compounds of formula Vc.

Compounds of formula Vh, that is compounds of formula IV.1 , or IV.2, wherein Z ¹ , Z ² , Z ³ , and Z ⁴ are N, and Y1 is an arene Q, substituted with A ^x (i.e. IV.1 ), or X1 (i.e. IV.2), can be obtained by reacting a compound of formula Vi, wherein X is a halogen such as CI or Br, with hydrazine in a cyclization reaction, followed by an oxidation in a separate step. Suitable reaction conditions are described in literature (cf. WO2012/12612, D. S. Liu et al., JACS 2012, 134, 792-795).

Preferably, hydrazine is employed as its hydrate and the subsequent oxidation step is per- formed with HONO as the oxidizing agent, which is preferably produced in situ by the treatment of an alkali metal nitrite such as e.g. NaN02 with an acid such as glacial acetic acid. The first step is generally carried out in the presence of a base, e.g. an alkali or alkaline earth metal carbonate such as K2CO3, CS2CO3, Na2C03, and CaC03, in a polar aprotic solvent such as e.g. ac- etonitrile. In turn, compounds of formula Vi can be prepared by reacting a compound of formula Vi with an activating/halogenating agent as described in literature (cf. WO2012/12612, D. S. Liu et al. JACS 2012, 134, 792-795. Suitable activating/halogenating agents are e.g. PCI ₅ , PBr ₅ , P(=0)Cl3, P(=0)Br3. Suitable solvents are e.g. halogenated hydrocarbons such as 1 ,2-dichloro- ethane, chloroform, dichloromethane, chlorobenzene. The transformation is usually carried out at temperatures from 0 °C to 120°C, preferably from 50°C to 100°C.

Compounds of formula Vj can be prepared by reacting a carboxylic acid of formula VI.1a, wherein X ^E is OH , or a carboxylic acid derivative of formula VI.1 b, wherein X ^E is a leaving group, preferably a halogen such as CI or Br, or Ci-C6-alkoxy, such as OCH3 or OC2H5, with an amine of formula Xp in an amidation reaction.

The amidation reaction is preferably carried out with acid chlorides of formula VI.1 b or by prior transformation of carboxylic acids of formula VI.1a with [(COCI)2] or SOC to the corresponding acid chlorides of formula VI.1 b, followed by reaction with an amine of formula Xp. Suitable reac- tion conditions are described in literature (cf. WO2004/22536). The reaction is generally carried out in the presence of an organic base such as NEt.3, iP^NEt, pyridine, or substituted pyridines such as collidine or lutidine. Optionally a nucleophilic catalyst such as DMAP can be employed in the reaction. Suitable solvents are halogenated hydrocarbons such as dichloromethane, chloroform, and chlorobenzene, or polar aprotic solvents such as THF, 1 ,4-dioxane, and DMF, or aromatic hydrocarbons such as benzene, toluene, 0-, m-, and p-xylene, or mixtures thereof. The transformation is usually carried out at temperatures from -40 °C to 100 °C, preferably from 0 °C to 30 °C. The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ an excess of Xm, based on VI.1. Alternatively, amidation of the carboxylic acid VI.1a is carried out in the presence of a coupling reagent. Suitable coupling reagents (activators) are known and are e.g. carbodiimides, such as DCC and Ν,Ν-diisopropyhcarbodiimide ("DCI"), benzotriazole derivatives such as HATU, HBTU, and HCTU, or phosphonium-derived activators, such as BOP, Py-BOP, Py-BrOP. Generally, the activator is used in excess. The benzotriazole and phosphonium coupling reagents are generally used in a basic medium.

As a rule, the compounds of formula I including their stereoisomers, salts, and N-oxides, and their precursors in the synthesis process, can be prepared by the methods described above. If individual compounds cannot be prepared via the above-described routes, they can be prepared by derivatization of other compounds I or the respective precursor or by customary modi- fications of the synthesis routes described. For example, in individual cases, certain compounds of formula I can advantageously be prepared from other compounds of formula I by derivatization, e.g. by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation, or by customary modifications of the synthesis routes described. The reaction mixtures are worked up in the customary manner, e.g. by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, e.g. on alumina or on silica gel. Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or trituration.

However, if the synthesis yields mixtures of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be interconverted during work-up for use or during application (e.g. under the action of light, acids or bases). Such conversions may also take place after use, e.g. in the treatment of plants in the treated plant. The organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix C _n -C _m indicates in each case the possible number of carbon atoms in the group.

The term "halogen" denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.

The term "alkyl" as used herein and in the alkyl moieties of alkylamino, alkylcarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl and alkoxyalkyl denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, prefer- ably 1 to 4 carbon atoms, more preferably from 1 to 3 carbon atoms. Examples of an alkyl group are methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl, iso-butyl, tert-butyl, n-pentyl, 1 -methyl- butyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 ,1 -dimethylpro- pyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -di- methylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dime- thylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 -methyl- propyl, and 1 -ethyl-2-methylpropyl.

The term "haloalkyl" as used herein and in the haloalkyl moieties of haloalkylcarbonyl, haloalk- oxycarbonyl, haloalkylthio, haloalkylsulfonyl, haloalkylsulfinyl, haloalkoxy and haloalkoxyalkyl, denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 car- bon atoms, frequently from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms. Preferred haloalkyl moieties are selected from Ci-C4-haloalkyl, more preferably from Ci-C3-haloalkyl or Ci-C2-haloalkyl, in particular from Ci-C2-fluoroalkyl such as fluoromethyl, difluoromethyl, trifluo- romethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, and the like.

The term "alkoxy" as used herein denotes in each case a straight-chain or branched alkyl group which is bonded via an oxygen atom and has usually from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms. Examples of an alkoxy group are methoxy, ethoxy, n-propoxy, iso-propoxy, n-butyloxy, 2-butyloxy, iso-butyloxy, tert.-butyloxy, and the like.

The term "alkoxyalkyl" as used herein refers to alkyl usually comprising 1 to 10, frequently 1 to 4, preferably 1 to 2 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 4, preferably 1 or 2 carbon atoms as defined above. Examples are CH2OCH3, CH2- OC2H5, 2-(methoxy)ethyl, and 2-(ethoxy)ethyl.

The term "haloalkoxy" as used herein denotes in each case a straight-chain or branched alkoxy group having from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms. Preferred haloalkoxy moieties include C1-C4- haloalkoxy, in particular Ci-C2-fluoroalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoro- methoxy, 1 -fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-flu- oroethoxy, 2-chloro-2,2-difluoro-ethoxy, 2,2dichloro-2-fluorethoxy, 2,2,2-trichloroethoxy, penta- fluoroethoxy and the like. The term "alkylthio "(alkylsulfanyl: S-alkyl)" as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (= Ci-C4-alkylthio), more preferably 1 to 3 carbon atoms, which is attached via a sulfur atom.

The term "haloalkylthio" as used herein refers to an alkylthio group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.

The term "alkylsulfinyl" (alkylsulfoxyl: S(=0)-Ci-C6-alkyl), as used herein refers to a straight- chain or branched saturated alkyl group (as mentioned above) having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (= Ci-C4-alkylsulfinyl), more preferably 1 to 3 carbon atoms bonded through the sulfur atom of the sulfinyl group at any position in the alkyl group.

The term "haloalkylsulfinyl" as used herein refers to an alkylsulfinyl group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.

The term "alkylsulfonyl" (S(=0)2-alkyl) as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (= Ci-C4-al- kylsulfonyl), preferably 1 to 3 carbon atoms, which is bonded via the sulfur atom of the sulfonyl group at any position in the alkyl group.

The term "haloalkylsulfonyl" as used herein refers to an alkylsulfonyl group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bro- mine and/or iodine.

The term "alkylcarbonyl" refers to an alkyl group as defined above, which is bonded via the carbon atom of a carbonyl group (C=0) to the remainder of the molecule.

The term "haloalkylcarbonyl" refers to an alkylcarbonyl group as mentioned above, wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine. The term "alkoxycarbonyl" refers to an alkylcarbonyl group as defined above, which is bonded via an oxygen atom to the remainder of the molecule.

The term "haloalkoxycarbonyl" refers to an alkoxycarbonyl group as mentioned above, wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.

The term "alkenyl" as used herein denotes in each case a singly unsaturated hydrocarbon radical having usually 2 to 10, frequently 2 to 6, preferably 2 to 4 carbon atoms, e.g. vinyl, allyl (2- propen-1 -yl), 1 -propen-1 -yl, 2-propen-2-yl, methallyl (2-methylprop-2-en-1 -yl), 2-buten-1 -yl, 3- buten-1 -yl, 2-penten-1 -yl, 3-penten-1 -yl, 4-penten-1 -yl, 1 -methylbut-2-en-1 -yl, 2-ethylprop-2-en- 1 -yl and the like.

The term "haloalkenyl" as used herein refers to an alkenyl group as defined above, wherein the hydrogen atoms are partially or totally replaced with halogen atoms.

The term "alkynyl" as used herein denotes in each case a singly unsaturated hydrocarbon radical having usually 2 to 10, frequently 2 to 6, preferably 2 to 4 carbon atoms, e.g. ethynyl, pro- pargyl (2-propyn-1 -yl), 1 -propyn-1 -yl, 1 -methylprop-2-yn-1 -yl), 2-butyn-1 -yl, 3-butyn-1 -yl, 1 -pen- tyn-1 -yl, 3-pentyn-1 -yl, 4-pentyn-1 -yl, 1 -methylbut-2-yn-1 -yl, 1 -ethylprop-2-yn-1 -yl and the like. The term "haloalkynyl" as used herein refers to an alkynyl group as defined above, wherein the hydrogen atoms are partially or totally replaced with halogen atoms. The term "cycloalkyl" as used herein and in the cycloalkyl moieties of cycloalkoxy and cycloal- kylthio denotes in each case a monocyclic cycloaliphatic radical having usually from 3 to 10 or from 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl or cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term "halocycloalkyl" as used herein and in the halocycloalkyl moieties of halocycloalkoxy and halocycloalkylthio denotes in each case a monocyclic cycloaliphatic radical having usually from 3 to 10 C atoms or 3 to 6 C atoms, wherein at least one, e.g. 1 , 2, 3, 4 or 5 of the hydrogen atoms, are replaced by halogen, in particular by fluorine or chlorine. Examples are 1 - and 2-fluo- rocyclopropyl, 1 ,2-, 2,2- and 2,3-difluorocyclopropyl, 1 ,2,2-trifluorocyclopropyl, 2,2,3,3-tetrafluo- rocyclpropyl, 1 - and 2-chlorocyclopropyl, 1 ,2-, 2,2- and 2,3-dichlorocyclopropyl, 1 ,2,2-trichloro- cyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 1 -,2- and 3-fluorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1 -,2- and 3-chlorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-dichlo- rocyclopentyl and the like.

The term "cycloalkenyl" as used herein and in the cycloalkenyl moieties of cycloalkenyloxy and cycloalkenylthio denotes in each case a monocyclic singly unsaturated non-aromatic radical having usually from 3 to 10, e.g. 3 or 4 or from 5 to 10 carbon atoms, preferably from 3- to 8 carbon atoms. Exemplary cycloalkenyl groups include cyclopropenyl, cycloheptenyl or cycloocte- nyl.

The term "halocycloalkenyl" as used herein and in the halocycloalkenyl moieties of halocyclo- alkenyloxy and halocycloalkenylthio denotes in each case a monocyclic singly unsaturated non- aromatic radical having usually from 3 to 10, e.g. 3 or 4 or from 5 to 10 carbon atoms, preferably from 3- to 8 carbon atoms, wherein at least one, e.g. 1 , 2, 3, 4 or 5 of the hydrogen atoms, are replaced by halogen, in particular by fluorine or chlorine. Examples are 3,3-difluorocyclopropen- 1 -yl and 3,3-dichlorocyclopropen-1 -yl.

The term "cycloalkenylalkyl" refers to a cycloalkenyl group as defined above which is bonded via an alkylene group, such as a Ci-Cs-alkyl group or a Ci-C4-alkyl group, in particular a methylene group (= cycloalkenylmethyl), to the remainder of the molecule.

The term "carbocycle" or "carbocyclyl" includes in general a 3- to 12-membered, preferably a 3- to 8-membered or a 5- to 8-membered, more preferably a 5- or 6-membered mono-cyclic, non-aromatic ring comprising 3 to 12, preferably 3 to 8 or 5 to 8, more preferably 5 or 6 carbon atoms. Preferably, the term "carbocycle" covers cycloalkyl and cycloalkenyl groups as defined above.

The term "heterocycle" or "heterocyclyl" includes in general 3- to 12-membered, preferably 5- or 6-membered, in particular 6-membered monocyclic heterocyclic non-aromatic radicals. The heterocyclic non-aromatic radicals usually comprise 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, wherein S-atoms as ring members may be present as S, SO or SO2. Examples of 5- or 6-membered heterocyclic radicals comprise saturated or unsaturated, non- aromatic heterocyclic rings, such as 2- and 3-azetidinyl, 2- and 3-oxetanyl, 2- and 3-thietanyl, 2- and 3-thietanyl-S-oxid (S-oxothietanyl), 2- and 3-thietanyl-S-dioxid (S-dioxothietanyl), 2- and 3- pyrrolidinyl, 2- and 3-tetrahydrofuranyl, 1 ,3-dioxolan-2-yl, thiolan-2-yl, S-oxothiolan-2-yl, S-diox- othiolan-2-yl, 4- and 5-oxazolidinyl, 1 ,3-dioxan-2-yl, 1 - and 3-thiopyran-2-yl, S-oxothiopyranyl, and S-dioxothiopyranyl. The term "hetaryl" or "aromatic heterocycle" includes monocyclic 5- or 6-membered heteroaro- matic radicals comprising as ring members 1 , 2, or 3 heteroatoms selected from N, O and S. Examples of 5- or 6-membered heteroaromatic radicals include pyridyl, i.e. 2-, 3-, and 4-pyridyl, pyrimidinyl, i.e. 2-, 4- and 5-pyrimidinyl, pyrazinyl, pyridazinyl, i.e. 3- and 4-pyridazinyl, thienyl, i.e. 2- and 3-thienyl, furyl, i.e. 2- and 3-furyl, pyrrolyl, i.e. 1 -, 2- and 3-pyrrolyl, oxazolyl, i.e. 2-, 4- and 5-oxazolyl, isoxazolyl, i.e. 3-, 4- and 5-isoxazolyl, thiazolyl, i.e. 2-, 3- and 5-thiazolyl, isothia- zolyl, i.e. 3-, 4- and 5-isothiazolyl, pyrazolyl, i.e. 1 -, 3-, 4- and 5-pyrazolyl, imidazolyl, i.e. 1 -, 2-, 4- and 5-imidazolyl, oxadiazolyl, e.g. 2- and 5-[1 ,3,4]oxadiazolyl, thiadiazolyl, e.g. 1 ,3,4-thiadia- zol-5-yl, 1 ,2,4-thiadiazol-3-yl, triazolyl, e.g. 1 ,3,4-triazol-2-yl, and 1 ,2,4-triazol-3-yl.

The terms "heterocyclyolalkyl" and "hetarylalkyl" refer to heterocyclyl or hetaryl, resp., as defined above which are bound via a Ci-C4-alkyl group, in particular a methyl group (= heterocy- clylmethyl or hetarylmethyl, resp.), to the remainder of the molecule.

With respect to the variables, the particularly preferred embodiments of the intermediates cor- respond to those of the compounds of the formula I.

In a particular embodiment, the variables of the compounds of the formula I have the following meanings, these meanings, both on their own and in combination with one another, being particular embodiments of the compounds of formula I. In a preferred embodiment, the compounds I are present in form of a mixture of compounds I.A, I.B, I.C, and I.D, where the trans-configurated compounds I.B and I.D are present in an amount of more than 50% by weight, in particular of at least 70% by weight, specifically of at least 90% by weight, based on the total weight of compounds I.A to I.D.

In one particularly preferred embodiment of the invention, the method comprises step of contacting the plant, parts of it, its propagation material, the pests, their food supply, habitat or breeding grounds a pesticidally effective amount of a trans compound.

Separation of the enantiomers can be achieved by methods known in the art, e.g. Kovalenko, Kulinkovich, Tetrahedron: Asymmetry 201 1 , 22, 26; or WO 2016/168059.

R ^1a and R ^1b are preferably identical. R ^1c and R ^1d are preferably both H

These groups represent preferably H, or halogen, such as CI and Br.

In one embodiment R ^1a and R ^1b are both halogen, such as CI and Br. In another embodiment R ^1a is H, and R ^1b is halogen, such as CI and Br. R ^2a is preferably selected from F, CI, Br, CF ₃ , and OCF ₃ .

R ^2b and R ^2c are independently preferably selected from H, F, CI, Br, CF3, and OCF3.

Particularly preferred is each one of the following combinations of R ^2a , R ^2b and R ^2c wherein each line of Table A denotes a substitution pattern of the phenyl ring ("A") bearing the R ^2a , R ^2b and R ^2c moieties. Table A

Groups A-8, A-9, and A-1 1 are more preferred patterns in formula I compounds. A-9 is particularly preferred.

Preferably in formula I compounds at most two of Z ¹ , Z ² , Z ³ , and Z ⁴ are N. Accordingly the Z ¹ to Z ⁴ containing heterocycle is pyrimidine, pyrazine, or pyridazine.

More preferably the ring is 2-pyrimidine. In any formula I heterocycles the ring atoms N and S can be oxidized, being N(0) _n and S(O) For clarity reasons usually only the not oxidized form is shown.

In one embodiment Q is a substituted phenyl having the structure Q1

wherein + is the bond to the remainder of the molecule and the index o is 0, 1 , 2, 3, or 4.

Preferably o is 0 or 1 , preferably 1 , and R ⁴ is in 3- or in 4-position. Preferably R ⁴ is halogen.

In another embodiment Q is a sixmembered hetaryl comprising one or two nitrogen atoms N as ring members, preferably being a pyridine. Such heterocycle having the structure Q2:

wherein + is the bond to the remainder of the molecule, and one of T ³ , T ⁴ , T ⁵ , T ⁶ is N, and the other thereof CH, or C-R ⁴ . Accordingly the index p in Q2 is 0, 1 , 2, or 3.

Preferably p is 0 or 1 , preferably 1 , and R ⁴ is in T ³ - or T ⁴ -position. Preferably R ⁴ is halogen. in case Q2 is a pyridine, preferably T ³ to T ⁵ are CH or C-R ⁴ , and T ⁶ is N.

In another embodiment Q is a C-bonded fivemembered ring. Such ring preferably contains one to four heteroatoms S, O or N, particularly one or two heteroatoms thereof. Examples are struc- tures Qa, Qb, Qc, and Qd. In such structures T ^a is S, O, or N-R ^N , and T ^b , T ^c , and T ^d are N, O, S, CH, or C-R ⁴ .

Ring Q preferably contains one or two hetero ring atoms S, O, or N. Preferably Q is bonded ortho to one heteroatom. Such structures preferably are Q3, Q4, or Q5.

In Q3 T ^a is preferably S, or N-R ^N , wherein R ^N preferably is H or Ci-C4-alkyl such as CH3.

R ⁴ is preferably ortho to A, and is preferably halogen such as CI. In Q4 T ^a -T ^b is preferably O-N. R ⁴ is preferably halogen or halomethyl, more preferably CF3.

In Q5 T ^a is preferably O, S, or N-R ^N , wherein R ^N preferably is H or Ci-C4-alkyl such as CH3, and T ^c is preferably N. R ⁴ is preferably halogen or halomethyl, more preferably CF3. Alternatively Q is bonded meta to one heteroatom. Such Q corresponds to structures Q6, Q7, Q8, and Q9.

In another embodiment Q is a fivemembered hetaryl bonded via a N-atom. This corresponds to Qe, wherein T ^b , T ^c , and T ^d are N, O, S, CH, or C-R ⁴ .

In Qe preferably T ^b is N, T ^c and T ^d are CR ⁴ . R ⁴ is preferably halogen or halomethyl, more preferably CF ₃ . Most preferably Q is thiophene or isoxazole, such as thiophen-2-yl, thiophen-3-yl, or isoxazol-5- yl. Particulary such Q correspond to Q3.1 , Q4.1 , and Q6.1 , wherein R ⁴ is preferably halogen or halomethyl. Variable U in groups A is preferably O.

In one embodiment A is A1.

In another embodiment A is A2, wherein the index n is preferably 1.

In one embodiment R ⁵ is H, Ci-C4-alkyl, Ci-C4-haloalkyl, or benzyl wherein the ring is unsub- stituted or corresponds to a group P.

In a preferred embodiment R ⁵ is phenyl or phenyl-alkyl which is substituted with halogen, and Ci-C4-haloalkyl. Particularly preferred meaning for R ⁵ is a group P, wherein # is the bond to the amide-N:

and R ⁵¹ , R ⁵² , and R ⁵³ are halogen or Ci-C4-haloalkyl.

In a particularly preferred embodiment R ⁵¹ is Br, R ⁵² , is CF3, and R ⁵³ is CF(CFs)2.

Particularly preferred is each one of the following combinations of R ⁵¹ , R ⁵² , and R ⁵³ wherein each line of Table P denotes a substitution pattern of the phenyl ring ("P") bearing the R ⁵¹ , R ⁵² , and R ⁵³ moieties. Table P

No. R51 _R 52 _R 53 No. R51 _R 52 _R 53

P-1 Br H CFs P-4 H CI CFs

P-2 CI H CFs P-5 Br H CH2CF3

P-3 H Br CFs P-6 CI H CH2CF3 No. R51 _R 52 _R 53

P-20 CFs CI CF2CF3

P-21 Br CFs CF(CF ₃ ) ₂

P-22 CI CFs CF(CF ₃ ) ₂

P-23 CFs Br CF(CFs) ₂

P-24 CFs CI CF(CF ₃ ) ₂

P-25 H H F

P-26 H H CI

P-27 H H Br

P-28 F H F

P-29 CI H CI

P-30 F H CI

P-31 CI H F

Groups P-21 , P-25, P-26, P-28, P-29, P-30, and P-31 are more preferred patterns in formula I compounds. P-25 and P-28 are particularly preferred.

R ⁶ is preferably Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, or phenyl, which rings are bonded either directly or via a CH2 spacer, and which rings are unsubstituted or substituted with 1 , 2, or 3 substituents R ^a which are preferably CN, CH3, or halogen; or

R ⁶ is preferably C3-C4-alkenyl, C3-C4-alkynyl, CH2C(=0)OR ³¹ , or benzyl wherein the ring is unsubstituted or corresponds to a group P. Preferred R ³¹ meanings are Ci-C6-alkyl such as CH3, C2H5, CH(CH ₃ ) ₂ , and C(CH ₃ ) ₃ , or phenyl, or benzyl.

R ⁶ is more preferably H, or Ci-C4-alkyl such as CH3 or CH2CH3, particularly H.

Preferred embodiments relate to each of following compounds of formula I, wherein the variables are as defined in the outset and the preferred embodiments:

In particular with a view to their use, preference is given to the compounds of formula I compiled in the tables below, which compounds correspond to formulae I.1 Q1 1 ^* , I.1 Q21 *, I.1 Q31 *, I.1 Q41 ^* , and 1.1 Q61 ^* , resp. Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.

Table 1 : Compounds of formula I.1 Q1 1 ^* in which R ⁴ is H, and the other variables for a compound correspond in each case to one row of Table B

Table 2 : Compounds of formula I.1 Q1 1 ^* in which R ⁴ is CI, and the other variables for a compound correspond in each case to one row of Table B Table 3 : Compounds of formula I.1 Q1 1 ^* in which R ⁴ is F, and the other variables for a compound correspond in each case to one row of Table B

Table 4 : Compounds of formula I.1 Q1 1 ^* in which R ⁴ is CH3, and the other variables for a compound correspond in each case to one row of Table B

Table 5 : Compounds of formula I.1 Q1 1 ^* in which R ⁴ is CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 6 : Compounds of formula I.1 Q21 ^* in which R ⁴ is H, and the other variables for a compound correspond in each case to one row of Table B

Table 7 : Compounds of formula I.1 Q21 ^* in which R ⁴ is CI, and the other variables for a com- pound correspond in each case to one row of Table B

Table 8 : Compounds of formula I.1 Q21 ^* in which R ⁴ is F, and the other variables for a compound correspond in each case to one row of Table B

Table 9 : Compounds of formula I.1 Q21 ^* in which R ⁴ is CH3, and the other variables for a compound correspond in each case to one row of Table B

Table 10 : Compounds of formula I.1 Q21 ^* in which R ⁴ is CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 1 1 : Compounds of formula I.1 Q31 ^* in which R ⁴ is H, and the other variables for a compound correspond in each case to one row of Table B

Table 12 : Compounds of formula I.1 Q31 ^* in which R ⁴ is CI, and the other variables for a com- pound correspond in each case to one row of Table B

Table 13 : Compounds of formula I.1 Q31 ^* in which R ⁴ is F, and the other variables for a compound correspond in each case to one row of Table B

Table 14 : Compounds of formula I.1 Q31 ^* in which R ⁴ is CH3, and the other variables for a compound correspond in each case to one row of Table B

Table 15 : Compounds of formula I.1 Q31 ^* in which R ⁴ is CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 16 : Compounds of formula I.1 Q41 ^* in which R ⁴ is H, and the other variables for a compound correspond in each case to one row of Table B

Table 17 : Compounds of formula I.1 Q41 ^* in which R ⁴ is CI, and the other variables for a com- pound correspond in each case to one row of Table B

Table 18 : Compounds of formula I.1 Q41 ^* in which R ⁴ is F, and the other variables for a compound correspond in each case to one row of Table B

Table 19 : Compounds of formula I.1 Q41 ^* in which R ⁴ is CH3, and the other variables for a compound correspond in each case to one row of Table B

Table 20 : Compounds of formula I.1 Q41 ^* in which R ⁴ is CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 21 : Compounds of formula I.1 Q61 ^* in which R ⁴ is H, and the other variables for a compound correspond in each case to one row of Table B

Table 22 : Compounds of formula I.1 Q61 ^* in which R ⁴ is CI, and the other variables for a com- pound correspond in each case to one row of Table B

Table 23 : Compounds of formula I.1 Q61 ^* in which R ⁴ is F, and the other variables for a compound correspond in each case to one row of Table B Table 24 : Compounds of formula I.1 Q61 ^* in which R ⁴ is CH3, and the other variables for a compound correspond in each case to one row of Table B

Table 25 : Compounds of formula I.1 Q61 ^* in which R ⁴ is CF3, and the other variables for a compound correspond in each case to one row of Table B

Table B

As used herein, the term "compound(s) of the present invention" or "compound(s) according to the invention" refers to the compound(s) of formula (I) as defined above, which are also referred to as "compound(s) of formula I" or "compound(s) I" or "formula I compound(s)", and includes their salts, tautomers, stereoisomers, and N-oxides. The present invention also relates to a mixture of at least one compound of the present invention with at least one mixing partner as defined herein after. Preferred are binary mixtures of one compound of the present invention as component I with one mixing partner as defined herein after 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 preferably 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.

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

The following list M of pesticides, grouped and numbered according the Mode of Action Classification of the Insecticide Resistance Action Committee (IRAC), together with which the compounds of the present invention can be used and with which potential synergistic effects might be produced, is intended to illustrate the possible combinations, but not to impose any limitation: M.1 Acetylcholine esterase (AChE) inhibitors from the class of: M.1A carbamates, e.g. aldi- carb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or from the class of M.1 B organophosphates, e.g. acephate, aza- methiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlor- mephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazi- non, dichlorvos/ DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O- (methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, me- carbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxyde- meton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phos- phamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyri- daphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiome- ton, triazophos, trichlorfon and vamidothion;

M.2. GABA-gated chloride channel antagonists such as: M.2A cyclodiene organochlorine compounds, as e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), as e.g. ethiprole, fipronil, flufiprole, pyrafluprole and pyriprole;

M.3 Sodium channel modulators from the class of M.3A pyrethroids, e.g. acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio- resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cy- permethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, me- perfluthrin,metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin and transfluthrin; or M.3B sodium channel modulators such as DDT or methoxychlor; M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class of M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M.4A.2: (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pen- tylidenehydrazinecarboximidamide; or M4.A.3: 1 -[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 5-propoxy-1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridine; or from the class M.4B nicotine;

M.5 Nicotinic acetylcholine receptor allosteric activators from the class of spinosyns, e.g. spinosad or spinetoram;

M.6 Chloride channel activators from the class of avermectins and milbemycins, e.g.

abamectin, emamectin benzoate, ivermectin, lepimectin or milbemectin;

M.7 Juvenile hormone mimics, such as M.7A juvenile hormone analogues as hydroprene, ki- noprene and methoprene; or others as M.7B fenoxycarb or M.7C pyriproxyfen;

M.8 miscellaneous non-specific (multi-site) inhibitors, e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, or M.8B chloropicrin, or M.8C sulfuryl fluoride, or M.8D borax, or M.8E tartar emetic;

M.9 Selective homopteran feeding blockers, e.g. M.9B pymetrozine, or M.9C flonicamid;

M.10 Mite growth inhibitors, e.g. M.10A clofentezine, hexythiazox and diflovidazin, or M.10B etoxazole;

M.1 1 Microbial disruptors of insect midgut membranes, e.g. bacillus thuringiensis OK bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is- raelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstakiand bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1 Ab, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1 ;

M.12 Inhibitors of mitochondrial ATP synthase, e.g. M.12A diafenthiuron, or M.12B organotin miticides such as azocyclotin, cyhexatin or fenbutatin oxide, or M.12C propargite, or M.12D tetrad ifon;

M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient, e.g.

chlorfenapyr, DNOC or sulfluramid;

M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, e.g. nereistoxin analogues as bensultap, cartap hydrochloride, thiocyclam or thiosultap sodium;

M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas as e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron or triflumuron;

M.16 Inhibitors of the chitin biosynthesis type 1 , as e.g. buprofezin;

M.17 Moulting disruptors, Dipteran, as e.g. cyromazine;

M.18 Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufeno- zide, halofenozide, fufenozide or chromafenozide;

M.19 Octopamin receptor agonists, as e.g. amitraz;

M.20 Mitochondrial complex III electron transport inhibitors, e.g. M.20A hydramethylnon, or M.20B acequinocyl, or M.20C fluacrypyrim;

M.21 Mitochondrial complex I electron transport inhibitors, e.g. M.21A METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfen- pyrad, or M.21 B rotenone; M.22 Voltage-dependent sodium channel blockers, e.g. M.22A indoxacarb, or M.22B meta- flumizone, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1 -[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(di- fluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methylphenyl)-2-[(4- chlorophenyl)[4-[methyl(methylsulfonyl)amino]

M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid derivatives, e.g. spirodiclofen, spiromesifen or spirotetramat;

M.24 Mitochondrial complex IV electron transport inhibitors, e.g. M.24A phosphine such as aluminium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;

M.25 Mitochondrial complex II electron transport inhibitors, such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen;

M.28 Ryanodine receptor-modulators from the class of diamides, as e.g. flubendiamide, chlor- antraniliprole (rynaxypyr®), cyantraniliprole (cyazypyr®), tetraniliprole, M.28.1 : (R)-3-Chlor-N1 - {2-methyl-4-[1 ,2,2,2-tetrafluor-1 -(trifluormethyl)ethyl]phenyl}-N2-(1 -methyl-2-methylsulfonyl- ethyl)phthalamid and M.28.2: (S)-3-Chlor-N 1 -{2-methyl-4-[1 ,2,2,2 -tetrafluor-1 -(trifluorome- thyl)ethyl]phenyl}-N2-(1 -methyl-2-methylsulfonylethyl)phthalamid, M.28.3: cyclaniliprole, M.28.4: methyl-2-[3,5-dibromo-2-({[3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}amino)ben- zoyl]-1 ,2-dimethylhydrazinecarboxylate; M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanyli- dene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluorom ethyl)pyrazole-3-carboxamide;

M.28.5b) N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6- methyl-phenyl]-2-(3-chlo- ro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5c) N-[4-chloro-2-[(di-2-propyl- lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chlo ro-2-pyridyl)-5-(trifluoromethyl)py- razole-3-carboxamide; M.28.5d) N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carba - moyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyra zole-3-carboxamide; M.28.5h) N-[4,6- dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl ]-2-(3-chloro-2-pyridyl)-5-(trifluo- romethyl)pyrazole-3-carboxamide; M.28.5i) N-[2-(5-Amino-1 ,3,4-thiadiazol-2-yl)-4-chloro-6-me- thylphenyl]-3-bromo-1 -(3-chloro-2-pyridinyl)-1 H-pyrazole-5-carboxamide; M.28.5j) 3-Chloro-1 - (3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1 -cyano-1 -methylethyl)amino]carbonyl]phenyl]-1 H-py- razole-5-carboxamide; M.28.5k) 3-Bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1 -(3,5- dichloro-2-pyridyl)-1 H-pyrazole-5-carboxamide; M.28.5I) N-[4-Chloro-2-[[(1 ,1 -dimethylethyl)ami- no]carbonyl]-6-methylphenyl]-1 -(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1 H-pyrazole-5-carbox- amide;

M.28.6: cyhalodiamide; or;

M.29. active compounds of unknown or uncertain mode of action, as e.g. afidopyropen, afoxo- laner, azadirachtin, amidoflumet, benzoximate, bifenazate, broflanilide, bromopropylate, chino- methionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, flupyradifurone, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyrida- lyl, pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim,

M.29.3: 1 1 -(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]-tetradec- 1 1 -en-10-one, M.29.4: 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1 -azaspi- ro[4.5]dec-3-en-2-one, M.29.5: 1 -[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl ]-3-(tri- fluoromethyl)-1 H-1 ,2,4-triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582); M.29.6, selected from M.29.6a) to M.29.6k): M.29.6a) (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2- pyridylidene]-2,2,2-trifluoro-acetamide; M.29.6b) (E/Z)-N-[1 -[(6-chloro-5-fluoro-3-pyridyl)methyl]- 2-pyridylidene]-2,2,2-trifluoro-acetamide; M.29.6c) (E/Z)-2,2,2-trifluoro-N-[1 -[(6-fluoro-3-pyri- dyl)methyl]-2-pyridylidene]acetamide; M.29.6d) (E/Z)-N-[1 -[(6-bromo-3-pyridyl)methyl]-2-pyridyli- dene]-2,2,2-trifluoro-acetamide; M.29.6e) (E/Z)-N-[1 -[1 -(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]- 2,2,2-trifluoro-acetamide; M.29.6f) (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2- difluoro-acetamide; M.29.6g) (E/Z)-2-chloro-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2- difluoro-acetamide; M.29.6h) (E/Z)-N-[1 -[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2- trifluoro-acetamide; M.29.6i) (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3- pentafluoro-propanamide.); M.29.6j) N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-tri- fluoro-thioacetamide; or M.29.6k) N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluor o- N'-isopropyl-acetamidine; M.29.8: fluazaindolizine; M.29.9.a): 4-[5-(3,5-dichlorophenyl)-5-(tri- fluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1 -oxothietan-3-yl)benzamide; or M.29.9.b): flux- ametamide; M.29.10: 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]- 1 H-pyrazole; M.29.1 1 , selected from M.29.1 1 b) to M.29.1 1 p): M.29.1 1.b) 3-(benzoylmethylamino)-N-[2-bro- mo-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluor o-benz- amide; M.29.1 1.c) 3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoro- methyl)ethyl]-6-(trifluoromethyl)phenyl]-benzamide; M.29.1 1 .d) N-[3-[[[2-iodo-4-[1 ,2,2,2-tetraflu- oro-1 -(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]car bonyl]phenyl]-N-meth

amide; M.29.1 1 .e) N-[3-[[[2-bromo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6-(trifluorome- thyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methy l-benzamide; M.29.1 1 .f) 4-fluoro-N- [2-fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6-(trifluoromethyl)phen no]carbonyl]phenyl]-N-methyl-benzamide; M.29.1 1 .g) 3-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ,2,2,2- tetrafluoro-1 -(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]car bonyl]phen

benzamide; M.29.1 1 .h) 2-chloro-N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]- 3-pyridinecarboxamide; M.29.1 1 .i) 4-cyano-N- [2-cyano-5-[[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]phenyl]carbamo- yl]phenyl]-2-methyl-benzamide; M.29.1 1 .j) 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;

M.29.1 1 .k) N-[5-[[2-chloro-6-cyano-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]phe- nyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.29.1 1 .1) N-[5-[[2-bromo-6-chlo- ro-4-[2,2,2-trifluoro-1 -hydroxy-1 -(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4^ ano-2-methyl-benzamide; M.29.1 1 .m) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(tri- fluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyan o-2-methyl-benzamide;

M.29.1 1.n) 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)pro- pyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.29.1 1.o) 4-cyano-N-[2-cyano-5-[[2,6-di- chloro-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-be n zamide; M.29.1 1.p) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phe- nyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.29.12, selected from

M.29.12a) to M.29.12m): M.29.12.a) 2-(1 ,3-Dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; M.29.12.b) 2-[6-[2-(5-Fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyr imidine; M.29.12.c) 2-[6-[2- (3-Pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; M.29.12.d) N-Methylsulfonyl-6-[2-(3-pyridyl)thia- zol-5-yl]pyridine-2-carboxamide; M.29.12.e) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridi- ne-2-carboxamide; M.29.12.f) N-Ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propan- amide; M.29.12.g) N-Methyl-N-[4-methyl-2-(3-pyndyl)thiazol-5-yl]-3-methylthio- propanamide; M.29.12.h) N,2-Dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methyl thio-propanamide;

M.29.12.1) N-Ethyl-2-methyl-N-[4-methyl-2-(3-pyri

M.29.12J) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-me thylthio-propanamide; M.29.12.k) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methyl thio-propanamide;

M.29.12.1) N-[4-Chloro-2-(3-pyndyl)thiazol-5-yl]-N-methyl-3-methylthio- propanamide;

M.29.12.m) N-[4-Chloro-2-(3-pyndyl)thiazol-5-yl]-N-ethyl-3-methylthio-p ropanamide;

M.29.14a) 1 -[(6-Chloro^-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M.29.14b) 1 -[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol; M.29.16a) 1 -isopropyl-N,5-dimethyl-N-pyri- dazin-4-yl-pyrazole-4-carboxamide; or M.29.16b) 1 -(1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyr- idazin-4-yl-pyrazole-4-carboxamide; M.29.16c) N,5-dimethyl-N-pyridazin-4-yl-1 -(2,2,2-trifluoro-1 - methyl-ethyl)pyrazole-4-carboxamide; M.29.16d) 1 -[1 -(1 -cyanocyclopropyl)ethyl]-N-ethyl-5-me- thyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16e) N-ethyl-1 -(2-fluoro-1 -methyl-propyl)-5- methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16f) 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl- N-pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16g) 1 -[1 -(1 -cyanocyclopropyl)ethyl]-N,5-dime- thyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16h) N-methyl-1 -(2-fluoro-1 -methyl-propyl]- 5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16i) 1 -(4,4-difluorocyclohexyl)-N-ethyl- 5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.29.16j) 1 -(4,4-difluorocyclohexyl)-N,5- dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide, M.29.17 selected from M.29.17a) to

M.29.17j): M.29.17a) N-(1 -methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M.29.17b) N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M.29.17c) N-cyclohexyl-2-(3-pyridi- nyl)-2H-indazole-4-carboxamide; M.29.17d) 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole- 4-carboxamide; M.29.17e) 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole -5-car- boxamide; M.29.17f) methyl 2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarbox ylate; M.29.17g) N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indaz ole-5-carboxamide;

M.29.17h) N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxa mide; Μ.29.17Ϊ) 2-(3-pyri- dinyl )-N-(2-pyrimidinylmethyl )-2H-indazole-5-carboxamide; M.29.17j) N-[(5-methyl-2-pyrazi- nyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide, M.29.18 selected from M.29.18a) to M.29.18d): M.29.18a) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsu lfa- nyl)propanamide; M.29.18b) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropro- pylsulfinyl)propanamide; M.29.18c) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclo- propyl)methylsulfanyl]-N-ethyl-propanamide; M.29.18d) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3- [(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-propanamid e; M.29.19 sarolaner, or M.29.20 lo- tilaner.

The commercially available compounds of the group M listed above may be found in The Pes- ticide Manual, 16th Edition, C. MacBean, British Crop Protection Council (2013) among other publications. The online Pesticide Manual is updated regularly and is accessible through http://bcpcdata.com/pesticide-manual.html. Another online data base for pesticides providing the ISO common names is http://www.alan- wood.net/pesticides.

M.4 cycloxaprid is known from WO2010/069266 and WO201 1/069456, M.4A.2, guadipyr, is known from WO2013/003977, and M.4A.3 (paichongding in China) is known from WO

07/101369. M.22B.1 is described in CN 10171577 and M.22B.2 in CN102126994. M.28.1 and M.28.2 are known from WO2007/101540. M.28.3 is described in WO2005/077934. M.28.4 is described in WO2007/043677. M.28.5a) to M.28.5d) and M.28.5h) are described in WO

07/006670, WO2013/024009 and WO2013/024010, Μ.28.5Ϊ) is described in WO201 1/085575, M.28.5j) in WO2008/134969, M.28.5k) in US201 1/046186 and M.28.5I) in WO2012/034403. M.28.6 can be found in WO2012/034472. M.29.3 is known from WO2006/089633 and M.29.4 from WO2008/06791 1. M.29.5 is described in WO2006/043635, and biological control agents on the basis of bacillus firmus are described in WO2009/124707. M.29.6a) to Μ.29.6Ϊ) listed under M.29.6 are described in WO2012/029672, and M.29.6j) and M.29.6k) in WO2013/129688. M.29.8 is known from WO2013/055584. M.29.9.a) is described in WO2013/050317. M.29.9.b) is described in WO2014/126208. M.29.10 is known from WO2010/060379. Broflanilide and M.29.1 1.b) to M.29.1 1 .h) are described in WO2010/018714, M.29.1 1 i) to M.29.1 1 .p) in WO 2010/127926. M.29.12.a) to M.29.12.c) are known from WO2010/006713, M.29.12.d) and M.29.12.e) are known from WO2012/000896, and M.29.12.f) to M.29.12.m) from WO

2010/129497. M.29.14a) and M.29.14b) are known from WO2007/101369. M.29.16.a) to M.29.16h) are described in WO2010/034737, WO2012/084670, and WO2012/143317, resp., and M.29.16i) and M.29.16j) are described in WO2015/055497. M.29.17a) to M.29.17.j) are described in WO2015/038503. M.29.18a) to M.29.18d) are described in US2014/0213448.

M.29.19 is described in WO2014/036056. M.29.20 is known from WO2014/090918.

The following list of fungicides, in conjunction with which the compounds of the present inven- tion can be used, is intended to illustrate the possible combinations but does not limit them: A) Respiration inhibitors

Inhibitors of complex III at Q ₀ site (e. g. strobilurins): azoxystrobin (A.1 .1 ), coumethoxy- strobin (A.1.2), coumoxystrobin (A.1 .3), dimoxystrobin (A.1.4), enestroburin (A.1 .5), fenamin- strobin (A.1 .6), fenoxystrobin/flufenoxystrobin (A.1 .7), fluoxastrobin (A.1 .8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin (A.1 .1 1 ), orysastrobin (A.1 .12), picoxy.strobin (A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1 .15), pyraoxystrobin (A.1 .16), trifloxystro- bin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2-meth- oxyimino-N-methyl-acetamide (A.1.18), pyribencarb (A.1 .19), triclopyricarb/chlorodincarb (A.1.20), famoxadone (A.1.21 ), fenamidone (A.1 .21 ), methyl-/V-[2-[(1 ,4-dimethyl-5-phenyl-pyra- zol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1 .22), 1 -[3-chloro-2-[[1 -(4-chlorophenyl)- 1 H-pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one (A.1.23), 1 -[3-bromo-2-[[1 -(4-chloro- phenyl)pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-on e (A.1 .24), 1 -[2-[[1 -(4-chlorophe- nyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetraz ol-5-one (A.1.25), 1 -[2-[[1 -(4-chloro- phenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tet razol-5-one (A.1.26), 1 -[2-[[1 -(2,4- dichlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-me thyl-tetrazol-5-one (A.1 .27), 1 -[2- [[4-(4-chlorophenyl)thiazol-2-yl]oxymethyl]-3-methyl-phenyl] -4-methyl-tetrazol-5-one (A.1.28), 1 - [3-chloro-2-[[4-(p-tolyl)thiazol-2-yl]oxymethyl]phenyl]-4-me thyl-tetrazol-5-one (A.1.29), 1 -[3-cy- clopropyl-2-[[2-methyl-4-(1 -methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-tetrazol -5-one (A.1.30), 1 -[3-(difluoromethoxy)-2-[[2-methyl-4-(1 -methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4- methyl-tetrazol-5-one (A.1.31 ), 1 -methyl-4-[3-methyl-2-[[2-methyl-4-(1 -methylpyrazol-3-yl)phe- noxy]methyl]phenyl]tetrazol-5-one (A.1 .32), 1 -methyl-4-[3-methyl-2-[[1 -[3-(trifluoromethyl)phe- nyl]-ethylideneamino]oxymethyl]phenyl]tetrazol-5-one (A.1 .33), (Ζ;2£)-5-[1

nyl)pyrazol-3-yl]-oxy-2-methoxyimino-/V,3-dimethyl-pent-3 -enamide (A.1 .34), (^2 )-5-[1 -(4- chloropheny pyrazol-S-y oxy^-methoxyimino-A^S-dimethyl-pent-S-enamide (A.1 .35), (Z,2E)-5- [1 -(4-chloro-2-fluoro-phenyl)pyrazol-3-yl]oxy-2-methoxyimin^

(A.1.36),

inhibitors of complex III at Qi site: cyazofamid (A.2.1 ), amisulbrom (A.2.2), [(3S,6S,7R,8R)- 8-benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]- 6-methyl-4,9-dioxo-1 ,5-dioxonan- 7-yl] 2-methylpropanoate (A.2.3), [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxy- pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2.4), [(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy -pyridine-2-carbonyl)amino]-6- methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2.5), [(3S,6S,7R,8R)-8-benzyl-3-[[3- (1 ,3-benzodioxol-5-ylmethoxy)-4-methoxy-pyridine-2-carbonyl]am ino]-6-methyl-4,9-dioxo-1 ,5- dioxonan-7-yl] 2-methylpropanoate (A.2.6); (3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridi- nyl)carbonyl]amino]-6-methyl-4,9-dioxo-8-(phenylmethyl)-1 ,5-dioxonan-7-yl 2-methylpropanoate (A.2.7), (3S,6S,7R,8R)-8-benzyl-3-[3-[(isobutyryloxy)methoxy]-4-metho xypicolinamido]-6-me- thyl-4,9-dioxo-1 ,5-dioxonan-7-yl isobutyrate (A.2.8);

inhibitors of complex II (e. g. carboxamides): benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), me- pronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.14), penthiopyrad (A.3.15), sedaxane (A.3.16), tecloftalam (A.3.17), thifluzamide (A.3.18), N-(4'-trifluoromethylthiobiphenyl-2-yl)-

3- difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide (A.3.19), N-(2-(1 ,3,3-trimethyl-butyl)-phe- nyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide (A.3.20), 3-(difluoromethyl)-1 -methyl-Nil ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.21 ), 3-(trifluoromethyl)-1 -methyl-N- (1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.22), 1 ,3-dimethyl-N-(1 ,1 ,3-trimethylin- dan-4-yl)pyrazole-4-carboxamide (A.3.23), 3-(trifluoromethyl)-1 ,5-dimethyl-N-(1 ,1 ,3-trimethylin- dan-4-yl)pyrazole-4-carboxamide (A.3.24), 1 ,3,5-trimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-

4- carboxamide (A.3.25), N-(7-fluoro-1 ,1 ,3-trimethyl-indan-4-yl)-1 ,3-dimethyl-pyrazole-4-carbox- amide (A.3.26), N-[2-(2,4-dichlorophenyl)-2-methoxy-1 -methyl-ethyl]-3-(difluoromethyl)-1 -me- thyl-pyrazole-4-carboxamide (A.3.27);

other respiration inhibitors (e. g. complex I, uncouplers): diflumetorim (A.4.1 ), (5,8-difluoro- quinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethylpyridin-2- yloxy)-phenyl]-ethyl}-amine (A.4.2); ni- trophenyl derivates: binapacryl (A.4.3), dinobuton (A.4.4), dinocap (A.4.5), fluazinam (A.4.6); ferimzone (A.4.7); organometal compounds: fentin salts, such as fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.1 1 ); and silthiofam (A.4.12); B) Sterol biosynthesis inhibitors (SBI fungicides)

C14 demethylase inhibitors (DMI fungicides): 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), fluquinconazole (B.1.10), flusilazole (B.1 .1 1 ), flutriafol (B.1 .12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1 .15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1 .19), paclo- butrazole (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), tri- adimenol (B.1 .28), triticonazole (B.1 .29), uniconazole (B.1 .30), 1 -[reA(2^3 )-3-(2-chlorophe- nyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1 H-[1 ,2,4]triazolo (B.1.31 ), 2-\re (2^3 ^-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]- 2H-[1 ,2,4]triazole-3-thiol (B.1.32), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1 ,2,4-triazol-1 -yl)pentan-2-ol (B.1 .33), 1 -[4- (4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -cyclopropyl-2-(1 ,2,4-triazol-1 -yl)ethanol (B.1.34), 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 ,2,4-triazol-1 -yl)butan-2-ol (B.1 .35), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1 -(1 ,2,4-triazol-1 -yl)butan-2-ol (B.1.36), 2-[4-(4-chloro- phenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1 -(1 ,2,4-triazol-1 -yl)butan-2-ol (B.1 .37), 2-[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 ,2,4-triazol-1 -yl)propan-2-ol (B.1 .38), 2-[2-chloro-

4- (4-chlorophenoxy)phenyl]-3-methyl-1 -(1 ,2,4-triazol-1 -yl)butan-2-ol (B.1 .39), 2-[4-(4-chlorophe- noxy)-2-(trifluoromethyl)phenyl]-1 -(1 ,2,4-triazol-1 -yl)pentan-2-ol (B.1 .40), 2-[4-(4-fluorophen- oxy)-2-(trifluoromethyl)phenyl]-1 -(1 ,2,4-triazol-1 -yl)propan-2-ol (B.1 .41 ), 2-[2-chloro-4-(4-chloro- phenoxy)phenyl]-1 -(1 ,2,4-triazol-1 -yl)pent-3-yn-2-ol (B.1 .51 ); imidazoles: imazalil (B.1.42), pe- furazoate (B.1.43), prochloraz (B.1 .44), triflumizol (B.1 .45); pyrimidines, pyridines and pipera- zines: fenarimol (B.1 .46), nuarimol (B.1 .47), pyrifenox (B.1 .48), triforine (B.1 .49), [3-(4-chloro-2- fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyrid yl)methanol (B.1 .50);

Delta14-reductase inhibitors: aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spirox- amine (B.2.8);

Inhibitors of 3-keto reductase: fenhexamid (B.3.1 );

C) Nucleic acid synthesis inhibitors

phenylamides or acyl amino acid fungicides: benalaxyl (C.1 .1 ), benalaxyl-M (C.1 .2), kiral- axyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (mefenoxam, C.1 .5), ofurace (C.1 .6), oxadixyl (C.1.7);

others: hymexazole (C.2.1 ), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4),

5- fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro-2-(4- fluorophenylmethoxy)pyrimidin-4-amine (C.2.7);

D) Inhibitors of cell division and cytoskeleton

- tubulin inhibitors, such as benzimidazoles, thiophanates: benomyl (D1.1 ), carbendazim (D1 .2), fuberidazole (D1.3), thiabendazole (D1 .4), thiophanate-methyl (D1.5); triazolopyrimidi- nes: 5-chloro-7-(4-methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine (D1.6);

other cell division inhibitors: diethofencarb (D2.1 ), ethaboxam (D2.2), pencycuron (D2.3), fluopicolide (D2.4), zoxamide (D2.5), metrafenone (D2.6), pyriofenone (D2.7);

E) Inhibitors of amino acid and protein synthesis

methionine synthesis inhibitors (anilino-pyrimidines): cyprodinil (E.1.1 ), mepanipyrim (E.1.2), pyrimethanil (E.1 .3);

protein synthesis inhibitors: blasticidin-S (E.2.1 ), kasugamycin (E.2.2), kasugamycin hy- drochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6), polyoxine (E.2.7), validamycin A (E.2.8);

F) Signal transduction inhibitors

MAP / histidine kinase inhibitors: fluoroimid (F.1 .1 ), iprodione (F.1 .2), procymidone (F.1 .3), vinclozolin (F.1 .4), fenpiclonil (F.1 .5), fludioxonil (F.1.6);

G protein inhibitors: quinoxyfen (F.2.1 );

G) Lipid and membrane synthesis inhibitors

- Phospholipid biosynthesis inhibitors: edifenphos (G.1.1 ), iprobenfos (G.1 .2), pyrazophos (G.1.3), isoprothiolane (G.1 .4);

lipid peroxidation: dicloran (G.2.1 ), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);

phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1 ), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7) and N-(1 -(1 -(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4- fluorophenyl) ester (G.3.8);

compounds affecting cell membrane permeability and fatty acides: propamocarb (G.4.1 ); fatty acid amide hydrolase inhibitors: oxathiapiprolin (G.5.1 ), 2-{3-[2-(1 -{[3,5-bis(difluoro- methyl-1 H-pyrazol-1 -yl]acetyl}piperidin-4-yl)-1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}phenyl methanesulfonate (G.5.2), 2-{3-[2-(1 -{[3, 5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]acetyl}piperidin-4- yl) 1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate (G.5.3);

H) Inhibitors with Multi Site Action

inorganic active substances: Bordeaux mixture (H.1.1 ), copper acetate (H.1 .2), copper hy- droxide (H.1 .3), copper oxychloride (H.1.4), basic copper sulfate (H.1.5), sulfur (H.1.6);

thio- and dithiocarbamates: 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);

organochlorine compounds (e. g. phthalimides, sulfamides, chloronitriles): anilazine (H.3.1 ), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1 ), N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl- benzenesulfonamide (H.3.12);

guanidines and others: guanidine (H.4.1 ), dodine (H.4.2), dodine free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1 H,5H-[1 ,4]dithi- ino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone (H.4.10);

I) Cell wall synthesis inhibitors

inhibitors of glucan synthesis: validamycin (1.1 .1 ), polyoxin B (1.1.2);

melanin synthesis inhibitors: pyroquilon (1.2.1 ), tricyclazole (1.2.2), carpropamid (1.2.3), di- cyclomet (I.2.4), fenoxanil (I.2.5);

J) Plant defence inducers acibenzolar-S-methyl (J.1.1 ), probenazole (J.1 .2), isotianil (J.1.3), tiadinil (J.1.4), prohexa- dione-calcium (J.1.5); phosphonates: fosetyl (J.1 .6), fosetyl-aluminum (J.1.7), phosphorous acid and its salts (J.1.8), potassium or sodium bicarbonate (J.1 .9);

K) Unknown mode of action

- bronopol (K.1.1 ), chinomethionat (K.1.2), cyflufenamid (K.1 .3), cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclomezine (K.1.7), difenzoquat (K.1 .8), difenzoquat-methylsulfate (K.1.9), diphenylamin (K.1.10), fenpyrazamine (K.1.1 1 ), flumetover (K.1.12), flusulfamide (K.1.13), flutianil (K.1.14), methasulfocarb (K.1 .15), nitrapyrin (K.1 .16), nitrothal-isopropyl (K.1.18), oxathiapiprolin (K.1 .19), tolprocarb (K.1 .20), oxin-copper (K.1 .21 ), proquinazid

(K.1.22), tebufloquin (K.1.23), tecloftalam (K.1 .24), triazoxide (K.1 .25), 2-butoxy-6-iodo-3-pro- pylchromen-4-one (K.1.26), 2-[3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]-1 -[4-(4-{5-[2-(prop-2-yn- 1 -yloxy)phenyl]-4,5-dihydro-1 ,2-oxazol-3-yl}-1 ,3-thiazol-2-yl)piperidin-1 -yl]ethanone (K.1.27), 2- [3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]-1 -[4-(4-{5-[2-fluoro-6-(prop-2-yn-1 -yloxy)phenyl]-4,5- dihydro-1 ,2-oxazol-3-yl}-1 ,3-thiazol-2-yl)piperidin-1 -yl]ethanone (K.1 .28), 2-[3,5-bis(difluorome- thyl)-1 H-pyrazol-1 -yl]-1 -[4-(4-{5-[2-chloro-6-(prop-2-yn-1 -yloxy)phenyl]-4,5-dihydro-1 ,2-oxazol-3- yl}-1 ,3-thiazol-2-yl)piperidin-1 -yl]ethanone (K.1 .29), N-(cyclopropylmethoxyimino-(6-difluoro- methoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide (K.1.30), N'-(4-(4-chloro-3-trifluorome- thyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine (K.1 .31 ), N'-(4-(4-fluoro-3-tri- fluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine (K.1 .32), N'-(2-me- thyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl )-N-ethyl-N-methyl formamidine

(K.1.33), N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy) -phenyl)-N-ethyl-N-methyl formamidine (K.1 .34), methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester (K.1.35), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridi ne (K.1 .36), 3-[5-(4-chloro- phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (pyrisoxazole) (K.1 .37), N-(6-methoxy-pyridin-3- yl) cyclopropanecarboxylic acid amide (K.1 .38), 5-chloro-1 -(4,6-dimethoxy-pyrimidin-2-yl)-2-me- thyl-1 H-benzoimidazole (K.1 .39), 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5- yl]-2-prop-2-ynyloxy-acetamide, ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1 .40), pi- carbutrazox (K.1 .41 ), pentyl N-[6-[[(Z)-[(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxyme- thyl]-2-pyridyl]carbamate (K.1 .42), 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phe- nyl]propan-2-ol (K.1 .43), 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phen-yl]pro pan-2-ol (K.1.44), 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1 -yl)quinoline (K.1 .45), 3-(4,4- difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1 -yl)quinoline (K.1 .46), 3-(4,4,5-trifluoro-3,3-dime- thyl-3,4-dihydroisoquinolin-1 -yl)quinoline (K.1 .47), 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1 ,4- benzoxazepine (K.1.48).

The fungicides described by common names, their preparation and their activity e.g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available.

The fungicides described by lUPAC nomenclature, their preparation and their pesticidal activity is also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031 ; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ; WO 01/56358; WO 02/22583; WO 02/40431 ; WO 03/10149; WO 03/1 1853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491 ; WO 04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721 ; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 1 1/028657, WO2012/168188, WO 2007/006670, WO 201 1/77514; WO13/047749, WO 10/069882, WO 13/047441 , WO 03/16303, WO 09/90181 , WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/024010 and WO 13/047441 , WO 13/162072, WO 13/092224, WO 1 1/135833).

Suitable mixing partners for the compounds of the present invention also include biopesticides. Biopesticides have been defined as a form of pesticides based on micro-organisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds, such as 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:

(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.

(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 (such as growth or developmental regulation, attractents, repellents or defence activators (e.g. induced resistance) and are relatively non-toxic to mammals.

Biopesticides for use against crop diseases have already established themselves on a variety of crops. For example, biopesticides already play an important role in controlling downy mildew diseases. Their benefits include: a 0-Day Pre-Harvest Interval, the ability to use under moderate to severe disease pressure, and the ability to use in mixture or in a rotational program with other registered pesticides.

A major growth area for biopesticides is in the area of seed treatments and soil amendments. Biopesticidal seed treatments are e.g. used to control soil borne fungal pathogens that cause seed rots, damping-off, root rot and seedling blights. They can also be used to control internal seed borne fungal pathogens as well as fungal pathogens that are on the surface of the seed. Many biopesticidal products also show capacities to stimulate plant host defenses and other physiological processes that can make treated crops more resistant to a variety of biotic and abiotic stresses or can regulate plant growth. Many biopesticidal products also show capacities to stimulate plant health, plant growth and/or yield enhancing activity.

The following list of biopesticides, in conjunction with which the compounds of the present invention can be used, is intended to illustrate the possible combinations but does not limit them: L) Biopesticides

L1 ) Microbial pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. megaterium, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B. solisalsi, B. subtil is, B. subtilis var. amyloliquefaciens, Candida oleophila, C. saitoana, Clavibac- ter michiganensis (bacteriophages), Coniothyrium minitans, Cryphonectria parasitica, Crypto- coccus albidus, DHophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f . catenu- late (also named Gliocladium catenulatum), Gliocladium roseum, Lysobacter antibioticus, L. en- zymogenes, Metschnikowia fructicola, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor a/bus, Paenibacillus alvei, Paenibacillus polymyxa, Pantoea vagans, Penicillium bilaiae, Phlebiopsis gig an tea, Pseudomonas sp., Pseudomonas ch/oraphis, Pseudozyma floc- culosa, Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces grise- oviridis, S. lydicus, S. violaceusniger, Talaromyces flavus, Trichoderma asperelloides, T. aspe- rellum, T. atroviride, T. fertile, T. gamsii, T. harmatum, T. harzianum, T. polysporum, T. stroma ileum, T. virens, T. viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticil! ium dahlia, zucchini yellow mosaic virus (avirulent strain);

L2) Biochemical pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity: harpin protein, Reynoutria sachalinensis extract;

L3) Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal activity: Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. ai- zawai, B. t. ssp. israelensis, B. t. ssp. galleriae, B. t. ssp. kurstaki, B. t. ssp. tenebrionis, Beau- veria bass/ana, B. brongniartii, Burkho/deria spp., Chromobacterium subtsugae, Cydia pomo- /7e//s granulovirus (CpGV), Cryptophlebia leucotreta granulovirus (CrleGV), Flavobacterium spp., Helicoverpa armigera nuc\eopo\y edrov\rus (HearNPV), Helicoverpa zea nucleopolyhe- drovirus (HzN PV), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV), Heterorhab- ditis bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, L. muscarium, Metarhizium anisopliae, Metarhizium anisopliae var. anisopliae, M. anisopliae var. acrid um, Nomuraea rileyi, Paecilomyces fumosoroseus, P. ///acinus, Paenibacillus popilliae, Pasteur/a spp., P. nishizawae, P. penetrans, P. ramosa, P. thornea, P. usgae, Pseudomonas fiuorescens, Spodoptera Iittoraiis nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, S. feltiae, S. kraussei, Streptomyces galbus, S. micro flavus,

L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal, pheromone and/or nemat- icidal 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, 1 1 , 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, 1 1 -tetradecatrienyl acetate, (Z,E)-9,12-tetrade- cadien-1 -yl acetate, Z-7-tetradecen-2-one, Z-9-tetradecen-1 -yl acetate, Z-1 1 -tetradecenal, Z-1 1 - tetradecen-1 -ol, extract of Chenopodium ambrosiodes, Neem oil, Quillay extract;

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. lupin/, Delftia acidovorans, Glomus intraradices, Mesorh/zob/um spp., Rhizobium legumi- nosarum bv. phaseoli, R. I. bv. trifolii, R. I. bv. viciae, R. tropic/ ^' , Sinorhizobium meliloti. The biopesticides from group L1 ) and/or L2) may also have insecticidal, acaricidal, mollus- cidal, 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.

Many of these biopesticides have been deposited under deposition numbers mentioned herein (the prefices such as 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 Blossom Protect® from bio-ferm GmbH, Austria), Azospirillum brasilense Sp245 originally isolated in wheat reagion of South Brazil (Passo Fundo) at least prior to 1980 (BR 1 1005; 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 ; US 8,445,255); B. amyloliquefaciens s>pp. plantarum Ώ1 1 isolated from air in Kikugawa-shi, Japan (US 20130236522; FERM BP-8234; e. g. Double Nickel™ 55 WDG from Certis LLC, USA), B. amyloliquefaciens spp. plantarum 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. amyloliquefaciens ssp. plantarum FZB42 isolated from soil in Brandenburg, Germany (DSM 231 17; J. Plant Dis. Prot. 105, 181-197, 1998; e. g. RhizoVital® 42 from AbiTEP GmbH, Ger- many), B. amyloliquefaciens ssp. plantarum MBI600 isolated from faba bean in Sutton Boning- ton, Nottinghamshire, U.K. at least before 1988 (also called 1430; NRRL B-50595;

US 2012/0149571 ; e. g. Integral® from BASF Corp., USA), B. amyloliquefaciens spp. plantarum 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. amyloliquefaciens spp. p/antarum l ^" J 1000 isolated in 1992 in South Dakoda, U.S.A. (also called 1 BE; ATCC BAA-390; CA 2471555; 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, US 6,406,690; e. g. Votivo® from Bayer CropScience LP, USA), B. pumilus GHA 180 isolated from apple tree rhizosphere 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 before 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; US 8,445,255), B. subtiiis F M also called UD 1022 or UD10-22 isolated from red beet roots in North America (ATCC PTA-1 1857; System. Appl. Microbiol. 27, 372- 379, 2004; US 2010/0260735; WO 201 1/109395); B. thuringiensis ssp. a/z<=?w=?/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. kurstakiS A isolated from E. saccharine 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 bass/ana GHA (ATCC 74250; e. g. BotaniGard® 22WGP from Laver- lam Int. Corp., USA), B. bass/ana JW-1 (ATCC 74040; e. g. Naturalis® from CBC (Europe) S.r.l., Italy), B. bass/ana PPRI 5339 isolated from the larva of the tortoise beetle Conchyloctenia punctata (NRRL 50757; e. g. Broad Band® 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, 201 1 ); 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), Coni- othyrium m/n/tans COWMW -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.), He/icoverpa armigera nuc\eopo\y edrov\rus (HearNPV) (J. Invertebrate Pathol. 107, 1 12-126, 201 1 ; e. g. Helicovex® from Adermatt Biocontrol, Switzerland; Diplomata® from Kop- pert, Brazil; Vivus® Max from AgBiTech Pty Ltd., Queensland, Australia), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV) (e. g. Gemstar® from Certis LLC, USA), Helicover-os es 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 anisopHae vdx. 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 ilacinus2 \ isolated from infected nematode eggs in the Philippines (AGAL 89/030550; W01991/02051 ; Crop Protection 27, 352-361 , 2008; e.g. Bio- Act®from Bayer CropScience AG, Germany and MeloCon® from Certis, USA), Paenibacillus s/i/e/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), Pasteur/a 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, 201 1 ; e.g. Clariva™ PN from Syngenta Crop Protection, LLC, USA), Penicillium bilaiae (also called P. bilaii) strains ATCC 18309 (= ATCC 74319), ATCC 20851 and/or ATCC 22348 (= ATCC 74318) originally isolated from soil in Alberta, Canada (Fertilizer Res. 39, 97-103, 1994; Can. J. Plant Sci. 78(1 ), 91 -102, 1998; US 5,026,417, WO 1995/017806; e. g. Jump Start®, Provide® from Novozymes Biologicals BioAg Group, Canada), Reynoutria sachalinensis extract (EP 0307510 B1 ; e.g. Regalia® SC from Marrone Biolnnovations, 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 Agricul- tural 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 -22 also called KRL-AG2 (ATCC 20847; BioControl 57, 687-696, 2012; e. g. Plantshield® from BioWorks Inc., USA or SabrEx™ from Advanced Bi- ological Marketing Inc., Van Wert, OH, USA).

According to the invention, the solid material (dry matter) of the biopesticides (with the exception of oils such as Neem oil) are considered as active components (e.g. to be obtained after drying or evaporation of the extraction or suspension medium in case of liquid formulations of the microbial pesticides).

In accordance with the present invention, the weight ratios and percentages used herein for a biological extract such as Quillay extract are based on the total weight of the dry content (solid material) of the respective extract(s).

The total weight ratios of compositions comprising at least one microbial pesticide in the form of viable microbial cells including dormant forms, can be determined using the amount of CFU of the respective microorganism to calclulate the total weight of the respective active component with the following equation that 1 x 10 ¹⁰ CFU 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, such as Stei- nernema feltiae.

When mixtures comprising microbial pesticides are employed in crop protection, the application rates preferably range from about 1 x 106 to 5 x 1015 (or more) CFU/ha, preferably from about 1 x 108 to about 1 x 1013 CFU/ha, and even more preferably from about 1 x 109 to about 1 x 1012 CFU/ha. In the case of (entomopathogenic) nematodes as microbial pesticides (e. g. Steinernema feltiae), the application rates preferably range inform about 1 x 105 to 1 x 1012 (or more), more preferably from 1 x 108 to 1 x 101 1 , even more preferably from 5 x 108 to 1 x 1010 individuals (e. g. in the form of eggs, juvenile or any other live stages, preferably in an infetive juvenile stage) per ha.

When mixtures comprising microbial pesticides are employed in seed treatment, the application rates with respect to plant propagation material preferably range from about 1 x 106 to 1 x 1012 (or more) CFU/seed. Preferably, the concentration is about 1 x 106 to about 1 x 109 CFU/seed. In the case of the microbial pesticides II, the application rates with respect to plant propagation material also preferably range from about 1 x 107 to 1 x 1014 (or more) CFU per 100 kg of seed, preferably from 1 x 109 to about 1 x 1012 CFU per 100 kg of seed.

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

An agrochemical composition comprises a pesticidally effective amount of a compound of the present invention or a mixture thereof. The term "pesticidally effective amount" is defined below.

The compounds of the present invention or the mixtures thereof can be converted into customary types of agro-chemical compositions, e. g. solutions, emulsions, suspensions, dusts, pow- ders, 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 propa- gation materials such as 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.

The compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

Examples for suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifi- ers and binders.

Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclo^hexanol; 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. Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & De- tergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl-sul- fonates, 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 alkyhnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethox-ylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Exam-pies of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol eth-oxylates.

Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as 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-subsititued 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 alkylpoly- glucosides. Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vi- nylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, e.g. quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable 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 ox- ide, 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 poly- acrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyeth- yleneamines.

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 present 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.

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

Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli- nones and benzisothiazolinones.

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

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

Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

Examples for composition types and their preparation are:

i) Water-soluble concentrates (SL, LS)

10-60 wt% of a compound I according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) up to 100 wt%. The active substance dissolves upon dilution with water.

ii) Dispersible concentrates (DC)

5-25 wt% of a compound I according to the invention and 1 -10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion.

iii) Emulsifiable concentrates (EC)

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

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)

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 suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.

vi) Water-dispersible granules and water-soluble granules (WG, SG)

50-80 wt% of a compound I according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

50-80 wt% of a compound I according to the invention are ground in a rotor-stator mill with ad- dition 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)

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. car- boxymethylcellulose) 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)

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. alko- hol 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)

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. methyl- methacrylate, 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 radi-cal 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 insolu-ble organic sol- vent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylme-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-mation of a pol- yurea microcapsule. The monomers amount to 1 -10 wt%. The wt% relate to the total CS composition.

xi) Dustable powders (DP, DS)

1 -10 wt% of a compound I according to the invention are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.

xii) Granules (GR, FG)

0.5-30 wt% of a compound I according to the invention is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.

xiii) Ultra-low volume liquids (UL)

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

The compositions types i) to xi) may optionally comprise further auxiliaries, such as 0.1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% colorants. The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active sub-stance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions cormprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 : 100 to 100: 1 , preferably 1 : 10 to 10: 1.

The user applies the composition according to the invention usually from a predosage de-vice, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical 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.

According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.

In a further embodiment, either individual components of the composition according to the in- vention or partially premixed components, e. g. components comprising compounds of the present 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, if appropriate.

In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e. g. components comprising compounds of the pre- sent invention and/or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.

The compounds of the present invention are suitable for use in protecting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, from at- tack or infestation by animal pests. Therefore, the present invention also relates to a plant protection method, which comprises contacting crops, plants, plant propagation materials, such as 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 present invention.

The compounds of the present invention are also suitable for use in combating or controlling animal pests. Therefore, the present 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, such as seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesti- cidally effective amount of a compound of the present invention. The compounds of the present invention are effective through both contact and ingestion. Furthermore, the compounds of the present invention can be applied to any and all developmental stages, such as egg, larva, pupa, and adult.

The compounds of the present invention can be applied as such or in form of compositions comprising them as defined above. Furthermore, the compounds of the present invention can be applied together with a mixing partner as defined above or in form of compositions comprising said mixtures as defined above. 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.

The application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, such as seeds, soil, or the area, material or environment by the pests.

Suitable application methods include inter alia soil treatment, seed treatment, in furrow appli- cation, 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 present invention. Suitable pheromones for specific crops and pests are known to a skilled person and publicly available from databases of pheromones and semiochemicals, such as http://www.pherobase.com.

As used herein, the term "contacting" includes both direct contact (applying the compounds/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 ground, plant, seed, soil, area, material or environment in which a pest is growing or may grow, of the animal pest or plant).

The term "animal pest" includes arthropods, gastropods, and nematodes. Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects. Insects, which are of particular relevance for crops, are typically referred to as crop insect pests.

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

The term "plant" includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize / sweet and field corn); beet, e.g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e.g. apples, pears, plums, peaches, nectarines, almonds, cherries, papayas, strawberries, raspberries, blackberries or gooseberries; le- guminous plants, such as beans, lentils, peas, alfalfa or soybeans; oil plants, such as rapeseed (oilseed rape), turnip rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, pumpkins, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as eggplant, spinach, lettuce (e.g. iceberg lettuce), chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers (e.g. carnation, petunias, geranium/pelargoniums, pansies and impatiens), shrubs, broad-leaved trees (e.g. poplar) or evergreens, e.g. conifers; eucalyptus; turf; lawn; grass such as grass for animal feed or ornamental uses. 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, such as cucumbers, tomatoes, beans or squashes.

The term "plant" is to be understood as including wild type plants and plants, which have been modified by either conventional breeding, or mutagenesis or genetic engineering, or by a combination thereof.

Plants, which have been modified by mutagenesis or genetic engineering, and are of particular commercial importance, include alfalfa, rapeseed (e.g. oilseed rape), bean, carnation, chicory, cotton, eggplant, eucalyptus, flax, lentil, maize, melon, papaya, petunia, plum, poplar, potato, rice, soybean, squash, sugar beet, sugarcane, sunflower, sweet pepper, tobacco, tomato, and cereals (e.g. wheat), in particular maize, soybean, cotton, wheat, and rice. In plants, which have been modified by mutagenesis or genetic engineering, one or more genes have been mutagen- ized or integrated into the genetic material of the plant. The one or more mutagenized or inte- grated genes are preferably selected from pat, epsps, crylAb, bar, cry1 Fa2, crylAc, cry34Ab1 , cry35AB1 , cry3A, cryF, cry1 F, mcry3a, cry2Ab2, cry3Bb1 , cry1A.105, dfr, barnase, vip3Aa20, barstar, als, bxn, bp40, asnl , and ppo5. The mutagenesis or integration of the one or more genes is performed in order to improve certain properties of the plant. Such properties, also known as traits, include abiotic stress tolerance, altered growth/yield, disease resistance, herbi- cide tolerance, insect resistance, modified product quality, and pollination control. Of these properties, herbicide tolerance, e.g. imidazolinone tolerance, glyphosate tolerance, or glufosi- nate tolerance, is of particular importance. Several plants have been rendered tolerant to herbicides by mutagenesis, e.g. Clearfield® oilseed rape being tolerant to imidazolinones, e.g. ima- zamox. Alternatively, genetic engineering methods have been used to render plants, such as soybean, cotton, corn, beets and oil seed rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate). Furthermore, insect resistance is of importance, in particular lepidopteran insect resistance and coleopteran insect resistance. Insect resistance is typically achieved by modifying plants by integrating cry and/or vip genes, which were isolated from Bacillus thuringiensis (Bt), and code for the respective Bt toxins. Genetically modified plants with insect resistance are commercially available under trade names including Wid- eStrike®, Bollgard®, Agrisure®, Herculex®, YieldGard®, Genuity®, and Intacta®. Plants may be modified by mutagenesis or genetic engineering either in terms of one property (singular traits) or in terms of a combination of properties (stacked traits). Stacked traits, e.g. the combination of herbicide tolerance and insect resistance, are of increasing importance. In general, all relevant modified plants in connection with singular or stacked traits as well as detailed infor- mation as to the mutagenized or integrated genes and the respective events are available from websites of the organizations "International Service for the Acquisition of Agri-biotech Applications (ISAAA)" (http://www.isaaa.org/gmapprovaldatabase) and "Center for Environmental Risk Assessment (CERA)" (http://cera-gmc.org/GMCropDatabase).

It has surprisingly been found that the pesticidal activity of the compounds of the present in- vention may be enhanced by the insecticidal trait of a modified plant. Furthermore, it has been found that the compounds of the present 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 present invention are suitable for combating pests, against which the insecticidal trait is not effective, so that a com- plementary insecticidal activity can advantageously be used.

The term "plant propagation material" refers to 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 for the multiplication 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 transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.

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

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/composi- tions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.

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 m ² , preferably from 0.001 to 20 g per 100 m ² .

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. The compounds of the present 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 present 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 pregermina- tion with a compound of the present 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.

The term "seed treatment" comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in-furrow application methods. Preferably, the seed treatment application of the active compound is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.

The present invention also comprises seeds coated with or containing the active compound. The term "coated with and/or containing" generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.

Suitable seed is e.g. seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, e.g. seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Bras- sica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.

In addition, the active compound may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineering, and which e.g. tolerate the action of herbicides or fungicides or insecticides. Such modified plants have been described in detail above.

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.

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.

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 antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.

Especially preferred FS formulations of the compounds of the present 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 such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.

In the treatment of seed, the application rates of the compounds of the invention are 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.

The invention therefore also relates to seed comprising a compound of the present invention, or an agriculturally useful salt thereof, as defined herein. The amount of the compound of the present invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.

The compounds of the present invention may also be used for improving the health of a plant. Therefore, the present 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 present invention.

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 phyto- toxic symptom on the treated plant or on the plant grown from the treated propagule or treated soil.

The terms "plant" and "plant propagation material" are defined above.

"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 such as 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 (for example, harvesting efficiency, processability).

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. 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 present 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.

As used herein, the term "non-crop insect pest" refers to pests, which are particularly relevant for non-crop targets, such as ants, termites, wasps, flies, ticks, mosquitos, crickets, or cockroaches.

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 such as ants, ter- mites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, 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 polyor- ganosaccharides, 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 described in the literature (e.g. http://www.phero- base.com), and are known to those skilled in the art.

For use in bait compositions, the typical content of active ingredient is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active compound.

Formulations of the compounds of the present invention as aerosols (e.g in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents, furthermore auxiliaries such as emulsifiers, perfume oils, if appropriate stabilizers, and, if required, propellants.

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

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

The compounds of the present invention and its respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.

Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of the present 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 or the like. 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.

The compounds of the present invention and its compositions can be used for protecting wooden materials such as trees, board fences, sleepers, frames, artistic artifacts, etc. and buildings, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities).

Customary application rates in the protection of materials are, for example, from 0.001 g to 2000 g or from 0.01 g to 1000 g of active compound per m ² treated material, desirably from 0.1 g to 50 g per m ² .

Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and/or insecticide. The compounds of the the present invention are especially suitable for efficiently combating animal pests such as arthropods, gastropods and nematodes including but not limited to:

insects from the order of Lepidoptera, e.g. Achroia grisella, Acleris spp. such as A. fimbriana, A. gloverana, A. variana; Acrolepiopsis assectella, Acronicta major, Adoxophyes spp. such as A. cyrtosema, A. orana; Aedia leucomelas, Agrotis spp. such as A. exclamationis, A. fucosa, A. ipsilon, A. orthogoma, A. segetum, A. subterranea; Alabama argillacea, Aleurodicus dispersus, Aisophiia pometaria, Ampelophaga rubiginosa, Amyeiois transiteiia, Anacampsis sarciteiia, Ana- gasta kuehniella, Anarsia lineatella, Anisota senator/a, Antheraea pernyi, Anticarsia (=Therme- sia) spp. such as A. gemmatalis; Apamea spp., Aproaerema modicella, Archips spp. such as A. argyrospila, A. fuscocupreanus, A. rosana, A. xyloseanus; Argyresthia conjugella, Argyroploce spp., Argyrotaenia spp. such as A. velutinana; Athetis mindara, Austroasca viridigrisea, Autog- rapha gamma, Autographa nigrisigna, Barathra brassicae, Bedel/la spp., Bonagota salubricola, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp. such as C. murinana, C. podana; Cacto blast is cactorum, Cadra cauteiia, Cat in go brazi lien sis, Calop- tilis theivora, Capua reticulana, Carposina spp. such as C. niponensis, C. sasakii; Cephus spp., Chaetocnema aridula, Cheimatobia brumata, Chilo spp. such as C. Indicus, C. suppressalis, C. partellus; Choreutis pariana, Choristoneura spp. such as C. conflictana, C. fumiferana, C. longi- cellana, C. murinana, C. occidentalis, C. rosaceana; Chrysodeixis (=Pseudoplusia) spp. such as C. eriosoma, C. includens; Cirphis unipuncta, Clysia ambiguella, Cnaphalocerus spp., Cna- phalocrocis medinalis, Cnephasia spp., Cochylis hospes, Coleophora spp., Co lias eurytheme, Conopomorpha spp., Conotrachelus spp., Cop/tarsia spp., Corcyra cepha/on/ca, Crambus ca/ig- inosellus, Crambus teterrellus, Crocidosema (=Epinotia) aporema, Cydalima (=Diaphania) per- spectalis, Cydia (=Carpocapsa) spp. such as C. pomonella, C. latiferreana; Dalaca noctuides, Datana integerrima, Dasychira pinicola, Dendrolim us spp. such as D. pini, D. spectabilis, D. sibi- ricus; Desmia funeralis, Diaphania spp. such as D. nitidalis, D. hyalinata; Diatraea grandiose/la, Diatraea saccharaiis, Diphthera f estiva, Earias spp. such as E. insuiana, E. vitteiia; Ecdytolopha aurantianu, Egira (=Xylomyges) curia/is, E/asmopa/pus lignosellus, Eldana saccharina, Endopi- za viteana, Ennomos subsignaria, Eoreuma loftini, Ephestia spp. such as E. cauteiia, E. eiuteiia, 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. such as F. subterranean; Galleria mellonella, Gracillaria spp., Gra- pholita spp. such as G. funebrana, G. molesta, G. inopinata; Ha 'lysidota spp., Harrisina ameri- cana, Hedylepta spp., Helicoverpa spp. such as H. armigera (=Heliothis armigera), H. zea (=He- liothis zea); Heliothis spp. such as H. assulta, H. subflexa, H. virescens; Hellula spp. such as H. undalis, H. rogatalis; Helocoverpa gelotopoeon, Hemileuca oliviae, Herpetogramma licarsisalis, Hibernia defoliaria, Hofmannophila pseudospretella, Homoeosoma electellum, Homona mag- nanima, Hypena scabra, Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus, Kakivoria flavofasciata, Keiferia lycopersicella, Lambdina fiscellaria fiscellaria, Lambdina fiscel- laria lugubrosa, Lamprosema indicata, Laspeyresia molesta, Leguminivora glycinivorella, Ler- odea eufala, Leucinodes orbonalis, Leucoma salicis, Leucoptera spp. such as L. coffeella, L. scitella; Leuminivora lycinivorella, Lithocolletis biancardeiia, Lithophane antennata, Llattia octo (=Amyna axis), Lobes/a botrana, Lophocampa spp., Loxagrotis albicosta, Loxostege spp. such as L sticticalis, L. cereralis; Lymantria spp. such as L. dispar, L. monacha; Lyonetia clerkella, Lyonetia prunifoliella, Malacosoma spp. such as M. americanum, M. californicum, M. constrict- tum, M. neustria; Mamestra spp. such as M. brassicae, M. configurata; Mamstra brassicae, Manduca spp. such as M. quinquemaculata, M. sexta; Marasmia spp, Marmara spp., Maruca testuiaiis, Megalopyge lanata, Meianchra picta, Meianitis leda, Mods spp. such as M. lapites, M. repanda; Mods latipes, Monochroa fragariae, Mythimna separata, Nemapogon cloacella, Ne- oleucinodes elegantalis, Nepytia spp., Nymphula spp., Oiketicus spp., Omiodes indicata, Om- phisa anastomosalis, Operophtera brumata, Orgy/a pseudotsugata, Or/a spp., Orthaga thyri- salis, Ostrinia spp. such as O. nubilalis; Oulema oryzae, Paleacrita vernata, Panolis flammea, Parnara spp., Papaipema nebris, Papilio cresphontes, Paramyelois transitella, Paranthrene re- galis, Paysandisia archon, Pectinophora spp. such as P. gossypieiia; Peridroma saucia, Per/ieu- coptera spp., such as P. coffeella; Phalera bucephala, Phryganidia californica, Phthorimaea spp. such as P. opercuieiia; Phyiiocnistis citreiia, Phyllonorycter spp. such as P. biancardeiia, P. crataegella, P. issikii, P. ringoniella; Pieris spp. such as P. brassicae, P. rapae, P. napi; Pilocro- cis tripunctata, Plathypena scabra, Platynota spp. such as P. flavedana, P. idaeusalis, P. stul- tana; Platyptilia carduidactyla, Plebejus argus, Plodia interpunctella, Plusia spp, Plutella maculi- pennis, Plutella xylostella, Pontia protodica, Prays spp., Prodenia spp., Proxenus /epigone, Pseuda/et/a spp. such as P. sequax, P. unipuncta; Pyrausta nubilalis, Rachiplusia nu, Rich/a albicosta, Rhizobius ventralis, Rhyacionia frustrana, Sabulodes aegrotata, Schizura concinna, Schoenobius spp., Schreckensteinia festaliella, Scirpophaga spp. such as S. incertulas, S. inno- tata; Scotia segetum, Sesamia spp. such as S. inferens, Seudyra subflava, Sitotroga cerealella, Sparganothis pilleriana, Spilonota lechriaspis, S. ocellana, Spodoptera (=Lamphygma) spp. such as 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. such as S. exitiosa, Tec/a solanivora, Telehin ileus, Thaumatopoea pityo- campa, Thaumatotibia (=Cryptophlebia) leucotreta, Thaumetopoea pityocampa, T heel a spp., Theresimima ampelophaga, Thyrinteina spp, Tildenia inconspicuella, Tinea spp. such as T. cloacella, T. pellionella; Tineola bisselliella, Tortrix spp. such as T. viridana; Trichophaga tapetz- ella, Trichoplusia spp. such as T. ni; Tuta (=Scrobipalpula) absoluta, Udea spp. such as U. rubi- galis, 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. such as A. anxius, A. planipennis, A. sinuatus; Agri- otes spp. such as A. fuscicollis, A. lineatus, A. obscurus; Alphitobius diaperinus, Amphimallus solstitialis, Anisandrus dispar, Anisoplia austriaca, Anobium punctatum, Anomala corpulenta, Anomala rufocuprea, Anoplophora spp. such as A. glabripennis; Anthonomus spp. such as A. eugenii, A. grandis, A. pomorum; Anthrenus spp., Aphthona euphoridae, Apion spp., Apogonia spp., Athous haemorrhoidalis, Atomaria spp. such as A. linearis; Attagenus spp., Aulacophora femora/is, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as B. lentis, B. pisorum, B. rufimanus; By discus be tula e, Callidiellum rufipenne, Callopistria floridensis, Callosobruchus chinensis, Cameraria ohridella, Cassida nebulosa, Cerotoma trifur- cata, Cetonia aurata, Ceuthorhynchus spp. such as C. assimilis, C. napi; Chaetocnema tibialis, Cleonus mendicus, Conoderus spp. such as C. vespertinus; Conotrachelus nenuphar, Cosmopolites spp., Costelytra zealandica, Crioceris asparagi, Cryptolestes ferrugineus, Cryptorhynchus lapathi, Ctenicera spp. such as C. destructor; Curculio spp., Cylindrocopturus spp., Cycloceph- ala spp., Dactylispa balyi, Dectes texanus, Dermestes spp., Diabrotica spp. such as D. undec- impunctata, D. speciosa, D. longicornis, D. semipunctata, D. virgifera; Diaprepes abbreviates, Dichocrocis spp., Dicladispa armigera, DHoboderus abderus, Diocalandra frumenti (Diocalandra stigmaticollis), Enaphalodes rufulus, Epilachna spp. such as E. varivestis, E. vigintioctomacu- lata; Epitrix spp. such as E. hirtipennis, E. similaris; Eutheoia humiiis, Eutinobothrus brasiiiensis, Fa us tin us cubae, Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Hylamorpha elegans, Hylobius abietis, Hylotrupes bajulus, Hypera spp. such as H. brun- neipennis, H. postica; Hypomeces squamosus, Hypothenem us spp., Ips typographus, Lachno- sterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lath ridi us spp., Lema spp. such as L. bilineata, L. meianopus; Leptinotarsa spp. such as L. decern lineata ; Leptispa pyg- maea, Limonius californicus, Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp., Lyctus spp. such as L. bruneus; Liogenys fuscus, Macrodactylus spp. such as M. subspinosus; Maladera matrida, Megaplatypus mutates, Megascelis spp., Me/anotus communis, Meligethes spp. such as M. aeneus; Melolontha spp. such as M. hippocastani, M. melolontha; Metamasius hemip- terus, Microtheca spp., Migdolus spp. such as M. fryanus, Monocham us spp. such as M. alter- natus; Naupactus xanthographus, Niptus hololeucus, Oberia brevis, O em on a hirta, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorrhynchus suicatus, Otiorrhynchus ovatus, Otiorrhynchus suicatus, Ouiema meianopus, Ouiema oryzae, Oxycetonia jucunda, Phaedon spp. such as P. brassicae, P. cochieariae; Phoracantha recurva, Phyiiobius pyri, Phyl- lopertha horticola, Phyllophaga spp. such as P. helleri; Phyllotreta spp. such as P. chrysoceph- ala, P. nemo rum, P. s trio/a ta, P. vittu/a; Phyllopertha horticola, Pop/ilia japonica, Premnotrypes spp., Psacothea hilaris, Psylliodes chrysocephala, Prostephanus truncates, Psylliodes spp., Pti- nus spp., Pulga saltona, Rhizopertha dominica, Rhynchophorus spp. such as R. billineatus, R. ferrugineus, R. pal ma rum, R. phoenicis, R. vulneratus; Saperda Candida, Scolytus schevyrewi, Scyphophorus acupunctatus, Sitona lineatus, Sitophilus spp. such as S. granaria, S. oryzae, S. zeamais; Sphenophorus spp. such as S. levis; Stegobium paniceum, Sternechus spp. such as S. subsignatus; Strophomorphus ctenotus, Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp. such as T. castaneum; Trogoderma spp., Tychius spp., Xylotrechus spp. such as X. pyrrhoderus; and, Zabrus spp. such as Z. tenebri- oides;

insects from the order of Diptera e.g. Aedes spp. such as A aegypti, A. albopictus, A. vexans; Anastrepha ludens, Anopheles spp. such as A. albimanus, A. crucians, A. freeborni, A. gam- biae, A. leucosphyrus, A. maculipennis, A. minimus, A. quadrimaculatus, A. sinensis; Bactro- cera invadens, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chrysomyia spp. such as C. bezziana, C. hominivorax, C. macellaria; Chrysops atlanticus, Chrysops discalis, Chrysops silacea, Cochliomyia spp. such as C. hominivorax; Contarinia spp. such as C. sorghicola; Cordylobia anthropophaga, Culex spp. such as C. nigripalpus, C. pipi- ens, C. quinquefasciatus, C. tarsalis, C. tritaeniorhynchus; Culicoides furens, Culiseta inornata, Culiseta melanura, Cuterebra spp., Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Dasi- neura oxycoccana, Delia spp. such as D. antique, D. coarctata, D. platura, D. radicum; Dermat- obia hominis, Drosophila spp. such as D. suzukii, Fannia spp. such as F. canicularis; Gastraphi- lus spp. such as G. intestinaiis; Geomyza tipunctata, Glossina spp. such as G. fuscipes, G. mor- sitans, G pa/pa/is, G tachinoides; Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia spp. such as H. platura; Hypoderma spp. such as H. lineata; Hyppobosca spp., Hydrellia philippina, Leptoconops torrens, Liriomyza spp. such as L. sativae, L. trifolii; Lucilia spp. such as L. caprina, L. cuprina, L. sericata; Lycoria pectoraiis, Mansonia titiiianus, Mayetioia spp. such as M. destructor; Musca spp. such as M. autumnalis, M. domestica; Muscina stabu- lans, Oestrus spp. such as O. ovis; Opomyza florum, Oscinella spp. such as O. frit; Orseolia oryzae, Pegomya hysocyami, Phlebotomus argentipes, Phorbia spp. such as P. antiqua, P. brassicae, P. coarctata; Phytomyza gymnostoma, Prosimuiium mixtum, Psiia rosae, Psorophora columbiae, Psorophora discolor, Rhagoletis spp. such as R. cerasi, R. cingulate, R. indifferens, R. mendax, R. pomonella; Rivellia quadrifasciata, Sarcophaga spp. such as S. haemorrhoidalis; Simulium vittatum, Sitodiplosis mosellana, Stomoxys spp. such as S. calcitrans; Tabanus spp. such as T. atratus, T. bovinus, T. lineola, T. similis; Tannia spp., Thecodiplosis japonensis, Tip- ula oleracea, Tipula paludosa, and Wohlfahrtia spp;

insects from the order of Thysanoptera for example, Baliothrips biformis, Dichromothrips cor- betti, Dichromothrips ssp., Echinothrips americanus, Enneothrips flavens, Frankliniella spp. such as F. fusca, F. occidentalis, F. tritici; Heliothrips spp., Hercinothrips femora/is, Kakothrips spp., Microcephalothrips abdominalis, Neohydatothrips samayunkur, Pezothrips kellyanus, Rhipiphorothrips cruentatus, Scirtothrips spp. such as S. citri, S. dorsalis, S. perseae; Stenchae- tothrips spp, Taeniothrips cardamoni, Taeniothrips inconsequens, Thrips spp. such as T. imagines, T. hawaiiensis, T. oryzae, T. pa I mi, T. parvispinus, T. tabaci;

insects from the order of Hemiptera for example, Acizzia jamatonica, Acrosternum spp. such as A. hilare; Acyrthosipon spp. such as A. onobrychis, A. pisum; Adelges laricis, Adelges tsu- gae, Adelphocoris spp., such as A. rapidus, A. superbus; Aeneolamia spp., Agonoscena spp., Aulacorthum solani, Aleurocanthus woglumi, Aleurodes spp., Aleurodicus disperses, Aleurolo- bus barodensis, Aleurothrixus spp., Amrasca spp., Anasa tristis, Antestiopsis spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphidula nasturtii, Aphis spp. such as A. craccivora, A. fabae, A. forbesi, A. gossypii, A. grossulariae, A. maidiradicis, A. pomi, A. sambuci, A. schneideri, A. spiraecola; Arboridia apicalis, Arilus critatus, Aspidiella spp., Aspidiotus spp., Ata- nus spp., Aulacaspis yasumatsui, Aulacorthum solani, Bactericera cockerelli (Paratrioza cockerelli), Bemisia spp. such as B. argentifolii, B. tabaci (Aleurodes tabaci); Blissus spp. such as B. leucopterus; Brachycaudus spp. such as B. cardui, B. helichrysi, B. persicae, B. prunicola;

Brachycolus spp., Brachycorynella asparagi, Brevicoryne brassicae, Cacopsylla spp. such as C. fulguralis, C. pyricola (Psylla pir/J; Calligypona marginata, Calocoris spp., Campylomma livida, Capitophorus horni, Carneocephala fulgida, Cavelerius spp., Ceraplastes spp., Ceratovacuna lanigera, Ceroplastes ceriferus, Cerosipha gossypii, Chaetosiphon fragaefolii, Chionaspis te- galensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Ci- mexspp. such as C. hemipterus, C. lectuiarius; Coccomytiius ha/ii, Coccus spp. such as C hes- per/dum, C pseudomagnoliarum, Corythucha arcuata, Creontiades dilutus, Cryptomyzus ribis, Chrysomphalus aonidum, Cryptomyzus ribis, Ctenarytaina spatulata, Cyrtopeltis notatus, Dalbu- lus spp., Dasynus piperis, Dialeurodes spp. such as D. citrifolii; Dalbulus maidis, Diaphorina spp. such as D. citri; Diaspis spp. such as D. bromeliae; Dichelops furcatus, Diconocoris he- wetti, Dora/is spp., Dreyfus/a nordmannianae, Dreyfus/a piceae, Drosicha spp., Dysaphis spp. such as D. plantaginea, D. pyri, D. radicola; Dysaulacorthum pseudosolani, Dysdercus spp. such as D. cingulatus, D. intermedins; Dysmicoccus spp., Edessa spp., Geocoris spp., Em- poasca spp. such as E. fabae, E. solana; Epidiaspis leperii, Eriosoma spp. such as E. lanig- erum, E. pyricola; Erythroneura spp., Eurygaster spp. such as E. integriceps; Euscelis bilobatus, Euschistus spp. such as E. heros, E. impictiventris, E. servus; Fiorinia theae, Geococcus coffeae, Glycaspis brimblecombei, Halyomorpha spp. such as H. halys; Heliopeltis spp., Ho- malodisca vitripennis (=H. coagulata), Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lac- tucae, lcerya spp. such as I. purchase; Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lecanoideus floccissimus, Lepidosaphes spp. such as L. ulmi; Leptocorisa spp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp. such as L. hesperus, L. lineolaris, L. pra- tensis; Maconellicoccus hirsutus, Marchalina hellenica, Macropes excavatus, Macrosiphum spp. such as M. rosae, M. avenae, M. euphorbiae; Macrosteles quadrilineatus, Mahanarva fimbrio- lata, Megacopta cribraria, Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari, Melano- callis (=Tinocallis) caryaefoliae, Metca fie/la spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzocallis coryli, Murgantia spp., Myzus spp. such as M. ascalonicus, M. cerasi, M. nicotianae, M. persicae, M. varians; Nasonovia ribis-nigri, Neotoxoptera formosana, Neomegalotomus spp, Nephotettix spp. such as N. malayanus, N. nigropictus, N. parvus, N. vi- rescens; Nezara spp. such as N. viridula; Niiaparvata lugens, Nysius huttoni, Oebalus spp. such as O. pugnax; Oncometopia spp., Orthezia praelonga, Oxycaraenus hyalinipennis, Parabemisia myricae, Parlatoria spp., Parthenolecanium spp. such as P. corn/, P. persicae; Pemphigus spp. such as P. bursar/us, P. popu/ivenae; Peregrinus maidis, Perkinsiella saccharic/da, Phenacoc- cus spp. such as P. aceris, P. gossypii; Phloeomyzus passer/nil, Phorodon humu/i, Phylloxera spp. such as P. devastatrix, Piesma quadrata, Piezodorus spp. such as P. guildinii; Pinnaspis aspidistrae, Planococcus spp. such as P. citri, P. ficus; Prosapia bicincta, Protopulvinaria pyri- formis, Psallus seriatus, Pseudacysta persea, Pseudaulacaspis pentagona, Pseudococcus spp. such as P. comstocki; Psylla spp. such as P. mali; Pteromalus spp., Pulvinaria amygdali, Pyrilla spp., Quadraspidiotus spp., such as Q. perniciosus; Quesada gigas, Rastrococcus spp., Redu- vius senilis, Rhizoecus americanus, Rhodnius spp., Rhopa/omyzus asca/on/cus, Rhopalosi- phum spp. such as R. pseudobrassicas, R. insertum, R. maidis, R. pad/; Sagatodes spp., Sahl- bergella singularis, Saissetia spp., Sappaphis mala, Sappaphis mali, Scaptocoris spp., Scaph- oides titan us, 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. such as T. accerra, T. perditor; Tibraca spp., Tomaspis spp., Toxoptera spp. such as T. aurantii; Trialeu- rodes spp. such as T. abutilonea, T. ricini, T. vaporariorum; Triatoma spp., Trioza spp., Typhlo- cyba spp., Unaspis spp. such as U. citri, U. yanonensis; and Viteus vitifolii,

Insects from the order Hymenoptera e.g. Acanthomyops interjectus, Athalia rosae, Atta spp. such as A. capiguara, A. cephaiotes, A. cephaiotes, A. laevigata, A. robusta, A. sexdens, A. tex- ana, Bombus spp., Brachymyrmex spp., Camponotus spp. such as C. floridanus, C. pennsyl- vanicus, C. modoc; Cardiocondyla nuda, Chalibion sp, Crematogaster spp., Dasymutilla occi- dentalis, Diprion spp., Dolichovespula maculata, Dorymyrmex spp., Dryocosmus kuriphilus, Formica spp., Hoplocampa spp. such as H. minuta, H. testudinea; Iridomyrmex humilis, Lasius spp. such as L. niger, Linepithema humile, Liometopum spp., Leptocybe invasa, Monomorium spp. such as M. pharaonis, Monomorium, Nylandria fuiva, Pachycondyla chinensis, Paratrechina lon- gicornis, Paravespula spp., such as P. germanica, P. pennsylvanica, P. vulgaris; Pheidole spp. such as P. megacephala; Pogonomyrmex spp. such as P. barbatus, P. californicus, Polistes ru- biginosa, Prenolepis impairs, Pseudomyrmex gracilis, Schelipron spp., Sirex cyaneus, Solenop- sis spp. such as S. geminata, S.invicta, S. molesta, S. richteri, S. xy/oni, Sphecius speciosus, Sphex spp., Tapinoma spp. such as T. melanocephalum, T. sessile; Tetramorium spp. such as T. caespitum, T. bicarinatum, Vespa spp. such as V. crabro; Vespula spp. such as 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, Gryllo- talpa spp. such as G. africana, G. gryllotalpa; Gryllus spp., Hieroglyphus daganensis, Kraus- saria angulifera, Locusta spp. such as L. migratoria, L. pardalina; Melanoplus spp. such as M. bivittatus, M. femurrubrum, M. mexicanus, M. sanguinipes, M. spretus; Nomadacris septemfas- ciata, Oedaleus senegalensis, Scapteriscus spp., Schistocerca spp. such as 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, such as Amblyomma spp. (e.g. A. americanum, A. variegatum, A. maculatum), Argas spp. such as A. persicu), Boophilus spp. such as B. annulatus, B. decoloratus, B. microplus, Dermacentor spp. such as D.silvarum, D. andersoni, D. variabilis, Hyalomma spp. such as H. truncatum, Ixodes spp. such as /. ricinus, I. rubicundus, I. scapularis, I. holocyclus, I. pacificus, Rhipicephalus sanguineus, Ornithodorus spp. such as O. moubata, O. hermsi, O. turicata, Orni- thonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes spp. such as P. ovis, Rhipicephalus spp. such as R. sanguineus, R. appendiculatus, Rhipicephalus everts/, Rh/zog/y- phus spp., Sarcoptes spp. such asS. Scabiei, and Family Eriophyidae including Acer/a spp. such as A she/don/, A. anthocoptes, Acallitus spp., Aculops spp. such as A. lycopersici, A. pel- ekassi, Aculus spp. such as A. schlechtendali; Colomerus vitis, Epitrimerus pyri, Phyllocoptruta oleivora; Eriophytes rib/s and Eriophyes spp. such as Eriophyes sheldonr, Family Tarsonemidae including Hemitarsonem us spp., Phytonemus pallidus and Polyphagotarsonemus latus, Steno- tarsonemus spp. Steneotarsonemus spinkr ^' , Family Tenuipalpidae including Brevipalpus spp. such as B. phoenicis, Family Tetranychidae including Eotetranychus spp., Eutetranychus spp., Oligonychus spp., Petrobia latens, Tetranychus spp. such as T. cinnabarinus, T. evansi, T. kanzawai, T, pacificus, T. phaseulus, T. telarius and T. urticae, Bryobia praetiosar, Panonychus spp. such as P. ulmi, P. citri, Metatetranychus spp. and Oligonychus spp. such as O. pratensis, O. perseae, Vasates lycopersici, Raoiella indica, /¾/77/7yCarpoglyphidae including Carpogly- phus spp.; Penthaleidae spp. such as Halotydeus destructor, Family Demodicidae with species such as Demodexspp.; Family Trombicidea including Trombicula spp:, Family Macronyssidae including Ornothonyssus spp:, Family Pyemotidae including Pyemotes tritici, Tyrophagus pu- trescentiae; Family Acaridae including Acarus siro, Family Araneida including Latrodectus mac- tans, Tegenaria agrestis, Chiracanthium sp, Lycosa sp Achaearanea tepidariorum and Loxos- celes reclusa,

Pests from the Phylum Nematoda, for example, plant parasitic nematodes such as root-knot nematodes, Meloidogyne spp. such as M. hapla, M. incognita, M. javanica; cyst-forming nematodes, Globodera spp. such as G. rostochiensis; Heterodera spp. such as H. avenae, H. glyci- nes, H. schachtii, H. trifo/ii; Seed gall nematodes, Anguina spp:, Stem and foliar nematodes,

Aphe/enchoides spp. such as A. besseyi; Sting nematodes, Be/ono/aim us spp. such as B. longi- caudatus; Pine nematodes, Bursaphelenchus spp. such as B. lignicolus, B. xylophilus; Ring nematodes, Criconema spp., Criconemella spp. such as C. xenoplax and C. ornata; and, Cricone- moides spp. such as Criconemoides in formis; Mesocriconema spp.; Stem and bulb nematodes, Ditylenchus spp. such as 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. such as L. elongatus; Lesion nematodes, Pratylenchus spp. such as P. brachyurus, P. neglectus, P. pene- trans, P. curvitatus, P. goodeyi; Burrowing nematodes, Radopholus spp. such as R. similis; Rhadopholus spp.; Rhodopholus spp.; Reniform nematodes, Rotylenchus spp. such as R. ro- bustus, R. reniformis; Scutellonema spp.; Stubby-root nematode, Trichodorus spp. such as T. obtusus, T. primitivus; Paratrichodorus spp. such as P. minor; Stunt nematodes, Tylenchorhyn- chus spp. such as T. claytoni, T. dub/us; Citrus nematodes, Ty/enchu/us spp. such as T. semi- penetrans; Dagger nematodes, Xiphinema spp.; and other plant parasitic nematode species; Insects from the order Isoptera e.g. Calotermes flavicollis, Coptotermes spp. such as C. for- mosanus, C. gestroi, C. acinaciformis; Cornitermes cumulans, Cryptotermes spp. such as C. brevis, C. cavifrons; Giobitermes suifureus, Heterotermes spp. such as H. aureus, H. longiceps, H. tenuis; Leucotermes flavipes, Odontotermes spp., I ncisitermes spp. such as /. minor, I. Sny- der, Marginitermes hubbardi, Ma stotermes spp. such as M. darwiniensis Neocapritermes spp. such as N. opacus, N. parvus; Neotermes spp., Procornitermes spp., Zootermopsis spp. such as Z. angusticoiiis, Z. nevadensis, Reticulitermes spp. such as R. hesperus, R. tibialis, R. spera- tus, R. flavipes, R. grassei, R. lucifugus, R. santonensis, R. virginicus; Termes natalensis,

Insects from the order Blattaria e.g. Blatta spp. such as B. orientalis, B. lateralis; Blattella spp. such as B. asahinae, B. germanica; Leucophaea maderae, Panchlora nivea, Periplaneta spp. such as P. americana, P. australasiae, P. brunnea, P. fuligginosa, P. japonica; Supeila longi- palpa, Parcoblatta pennsylvanica, Eurycotis floridana, Pycnoscelus surinamensis,

Insects from the order Siphonoptera e.g. Cediopsylla simples, Ceratophyllus spp., Ctenoce- phalides spp. such as C. felis, C. cam ^' s, Xenopsylla cheopis, Pulex irritans, Trichodectes cam ^' s, Tung a penetrans, and Nosopsyllus fascia tus,

Insects from the order Thysanura e.g. Lepisma saccharina , Ctenolepisma urbana, and Ther- mobia domestica,

Pests from the class Chilopoda e.g. Geophilus spp., Scutigera spp. such as Scutigera coleop- trata,

Pests from the class Diplopoda e.g. Blaniulus guttulatus, Ju/us 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., such as Onychiurus armatus, Pests from the order Isopoda for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber,

Insects from the order Phthiraptera, e.g. Damalinia spp., Pediculus spp. such as Pediculus hu- manus capitis, Pediculus human us corporis, Pediculus human us humanus; Pthirus pubis, Haematopinus spp. such as Haematopinus eurysternus, Haematopinus suis, Linognathus spp. such as Linognathus vituii; Bovicoia bovis, Menopon gaiiinae, Menacanthus stramineus and So- lenopotes capillatus, Trichodectes spp.,

Examples of further pest species which may be controlled by compounds of fomula I include: from the Phylum Mollusca, class Bivalvia, for example, Dreissena spp.; class Gastropoda, e.g., Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Ga/ba spp., Lymnaea spp., On- comelania spp., Pomacea canaliclata, Succinea spp.; from the class of the helminths, e.g., Ancylostoma duodenale, Ancylostoma ceyianicum, Acyiostoma braziiiensis, Ancylostoma spp., As- can ^' s lubricoides, Ascaris spp., Brugia malayi, Brugia t/ ^' mori, 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. such as Haemonchus contortus; Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonim us spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercora lis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, T rich in ell a pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti. The compounds of the present invention are suitable for use in treating or protecting animals against infestation or infection by parasites. Therefore, the present invention also relates to the use of a compound of the present invention for the manufacture of a medicament for the treatment or protection of animals against infestation or infection by parasites. Furthermore, the present 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 present invention.

The present invention also relates to the non-therapeutic use of compounds of the present invention for treating or protecting animals against infestation and infection by parasites. Moreover, the present 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 parasiti- cidally effective amount of a compound of the present invention.

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

The present invention also relates to the non-therapeutic use of compounds of the present invention for controlling or combating parasites. Moreover, the present 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 present invention.

The compounds of the present 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 present invention can be applied to any and all developmental stages.

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

The compounds of the present invention can also be applied together with a mixing partner, which acts against pathogenic parasites, e.g. with synthetic coccidiosis compounds, poly- etherantibiotics such as Amprolium, Robenidin, Toltrazuril, Monensin, Salinomycin, Madurami- cin, Lasalocid, Narasin or Semduramicin, or with other mixing partners as defined above, or in form of compositions comprising said mixtures.

The compounds of the present invention and compositions comprising them can be applied orally, parenterally or topically, e.g. dermally. The compounds of the present invention can be systemically or non-systemically effective.

The application can be carried out prophylactically, therapeutically or non-therapeutically. Furthermore, the application can be carried out preventively to places at which occurrence of the parasites is expected.

As used herein, the term "contacting" includes both direct contact (applying the compounds/compositions directly on the parasite, including the application directly on the animal or excluding the application directly on the animal, e.g. at it's 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 present invention.

The term "locus" means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal. As used herein, the term "parasites" includes endo- and ectoparasites. In some embodiments of the present invention, endoparasites can be preferred. In other embodiments, ectoparasites can be preferred. Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chig- gers, gnats, mosquitoes and fleas.

The compounds of the present invention are especially useful for combating parasites of the following orders and species, respectively:

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides cam ^' s, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus; cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Peri plane ta am erica na, Peri plan eta japonica, Peri- planeta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis; flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes aibopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimacula- tus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pip/ens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Derma tobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina pa/pa/is, Glossina fuscipes, Glossina tachinoides, Ha em a tobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lu cilia caprina, Lu cilia cuprina, Lu cilia sericata, Lycoria pectoral is, Manso- nia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psoro- phora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sar- cophaga sp., Sim u Hum vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Taba- nus lineola, and Tabanus similis; lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus; ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocy- clus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor varia- bilis, Amblyomma americanum, Ambryomma macu latum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssus gallinae; Actinedida (Prostigmata) und Acaridida (Astigmata), e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listro- phorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Kne- midocoptes spp., Cytodites spp., and Laminosioptes spp; Bugs (Heteropterida): Cimex lectular- ius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongyius ssp., and Ar/ius cr/tatus; Anop\ur\da, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp.; Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. 7/7- menopon 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., CapiHaria spp.; Rhabditida, e.g. Rhabditis spp., Strongyloides spp., Helicephalobus spp.; Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Tri- chostrongylus spp., Haemonchus contortus, Ostertagia spp., Cooper/a spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollula- nus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Unci- naria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capiHaris, Proto- strongylus spp., Angiostrongylus spp., Parelaphostrongylus spp., Aleurostrongylus abstrusus, and Dioctophyma renale; Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi; e.g. Dracunculus medinensis (guinea worm); Spirurida, e.g. Thelazia spp., Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetalonema spp., Se tar/a 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. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multi- ceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplo- cephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp..

As used herein, the term "animal" includes warm-blooded animals (including humans) and fish. Preferred are mammals, such as 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 such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels. Particularly preferred are domestic animals, such as dogs or cats.

In general, "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 such as desired parasiticidal effect and duration, target species, mode of application, and the like.

Generally, it is favorable to apply the compounds of the present 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.

For oral administration to warm-blooded animals, the formula I compounds 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 formula I compounds may be administered 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 formula I compound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day. Alternatively, the formula I compounds may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The formula I compounds may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the formula I compounds may be formulated into an implant for subcuta- neous administration. In addition the formula I compound may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound.

The formula I compounds 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 formula I compound. In addition, the formula I compounds may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.

Suitable preparations are:

- Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;

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

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

- Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.

Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further auxiliaries such as acids, bases, buffer salts, preservatives, and solubilizers. Suitable auxiliaries for injection solutions are known in the art. The solu- tions 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.

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.

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

Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically. Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added. Suitable such auxiliaries are known in the art. Emulsions can be administered orally, dermally or as injections. Emulsions are either of the water-in-oil type or of the oil-in-water type. They are prepared by dissolving the active compound 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 such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances. Suitable hydrophobic phases (oils), suitable hydrophilic phases, suitable emulsifiers, and suitable further auxiliaries for emulsions are known in the art.

Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers. Suitable suspending agents, and suitable other auxiliaries for suspensions including wetting agents are known in the art.

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

For the production of solid preparations, the active compound is mixed with suitable excipi- ents, if appropriate with addition of auxiliaries, and brought into the desired form. Suitable auxiliaries for this purpose are known in the art.

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

Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 per cent by weight, preferably from 0.1 to 65 per cent by weight, more preferably from 1 to 50 per cent by weight, most preferably from 5 to 40 per cent by weight.

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

Furthermore, the preparations comprise the compounds of formula I against endoparasites in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 per cent by weight, very particularly preferably of 0.005 to 0.25 per cent by weight.

Topical application may be conducted with compound-containing shaped articles such as col- lars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.

Generally it is favorable to apply solid formulations which release compounds of the present 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.