The present invention relates to cyclopropyl compounds of formula I

wherein

R ^1a , R ^1b R ^1c , R ^1d are independently H, halogen, halomethyl, 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 ;

G, and Z are either

(i): G is O, S(0) _m , or N-R ^AZ , and Z is N(0) _n , or C-R ^A ; or

(ii): Z is O, S(0) _m , or N-R ^AZ , and G is N(0) _n , or C-R ^A ;

m is 0, 1 , or 2;

n is 0, or 1 ;

R ^A is independently H, halogen, CN, NO ₂ , OH, N(R ³¹ )R ³² ,Ci-C ₄ -alkyl, Ci-C ₄ -haloalkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -haloalkenyl, C ₂ -C ₄ -alkynyl, C ₂ -C ₄ -haloalkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -halocycloalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, S(0) _m -Ci-C ₄ -alkyl, S(0) _m -Ci- C ₄ -haloalkyl, Ci-C ₄ -haloalkylcarbonyl, C(=0)R ³³ , C(=0)0R ³³ , C(=0)N(R ³¹ )R ³² , S(0) _m N(R ³¹ )R ³² , or phenyl, wherein cycles are unsubstituted or substituted with halogen, CN, Ci-C ₄ -alkyl, or Ci-C ₂ -haloalkyl;

R ^AZ is as defined for R ^A ;

R ³ is H, halogen, CN, NO ₂ , OH, N(R ³¹ )R ³² , Ci-C ₆ -alkyl, C ₃ -C ₇ -cycloalkyl, C ₂ -C ₆ -alkenyl, C ₃ - C ₇ -cycloalkenyl, C ₂ -C ₆ -alkynyl, Ci-C ₆ -alkoxy, Ci-C ₆ -haloalkyl, C ₃ -C ₇ -halocycloalkyl, C ₂ -C ₆ - haloalkenyl, C ₃ -C ₇ -halocycloalkenyl, Ci-C ₆ -haloalkoxy, S(0) _m -Ci-C ₆ -alkyl, or S(0) _m -Ci-C ₆ - haloalkyl, in which aliphatic groups are unsubstituted, partially or fully substituted with one or more R ^a ;

R ³¹ is H, or Ci-C ₆ -alkyl,

R ³² is H, Ci-C ₆ -alkyl, Ci-C ₆ -haloalkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -alkynyl, C ₂ -C ₆ -haloalkynyl, or C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -halocycloalkyl, C ₃ -C ₆ -cycloalkylmethyl, or C ₃ -C ₆ -halocycloalkylmethyl which rings are unsubstituted or substituted with a CN;

R ^a is CN, N ₃ , N0 ₂ , SCN, SFs, Si(Ci-C ₄ -alkyl) ₃ , OR ³³ , OSO ₂ R ³³ , S(0) _m R ³³ , N(R ³¹ )R ³² , C(=0)N(R ³¹ )R ³² , C(=S)N(R ³¹ )R ³² , C(=0)0R ³³ , CH=NOR ³³ , C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ - 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-C ₆ -alkyl, Ci-C ₆ -haloalkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, CH ₂ -CN, C ₃ -C ₆ - cycloalkyl, C ₃ -C ₆ -halocycloalkyl, C ₃ -C ₆ -cycloalkylmethyl, C ₃ -C ₆ -halocyclo- alkylmethyl, 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 ³¹ )R ³² , C ₃ -C ₆ -cycloalkyl, or C ₃ -C ₆ -halocyclo- alkyl 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;

T ¹ ,T ² independently are N(0) _n or C-R ⁴ , provided that at least one is C-R ⁴ ;

R ⁴ is idependently as defined for R ³ ;

A 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 ³³ , C(=0)0R ³³ , CN, Ci-C ₆ -alkyl, Ci-C ₆ -alkoxy, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alky- nyl, C ₃ -C ₈ -cycloalkyl, N(R ³¹ )R ³² , phenyl or saturated, partially or fully unsaturated hetero- cycle, which groups are unsubstituted or substituted with one or more R ^a ; and wherein the rings are bonded directly or via Ci-C ₄ -alkylene spacer;

R ⁶ is H, Ci-C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, Cs-Cs-cycloalkyl, C ₃ -C ₈ -cycloalkyl-Ci-C ₄ - alkyl, Ci-C ₆ -alkylcarbonyl, Ci-C ₆ -alkoxycarbonyl, phenyl or saturated, partially or fully un- saturated heterocycle, which groups are unsubstituted or substituted with one or more R ^aa ; and wherein the rings are bonded directly or via Ci-C ₄ -alkylene spacer;

R ^aa is halogen, CN, Ci-C ₆ -alkyl, OR ³¹ , C(=NOR ⁵¹ )R ⁵² ; C(=0)N(R ³¹ )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 C ₃ -C ₆ -cycloalkyl, Ci-C ₆ -alkylidene, oxo, thioxo, imino, Ci-C ₆ -alkylimino, or Ci-C ₆ -alkoximino;

R ⁵¹ ,R ⁵² are independently H, Ci-C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, Cs-Cs-cycloal- kyl, C ₃ -C ₈ -cycloalkyl-Ci-C ₄ -alkyl, phenyl or saturated, partially or fully unsaturated heterocycle, which groups are unsubstituted or substituted with one or more halo- gen, CN, NO ₂ ; and wherein the rings are bonded directly or via Ci-C ₄ -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 ac- ceptable carrier.

The invention also provides a veterinary composition comprising at least one compound of for- mula I, a stereoisomer thereof and/or a veterinarily acceptable salt thereof and at least one liq uid 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 corn- prises 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 materi- als (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 effec- tive amount of a compound of formula I or a veterinarily acceptable salt thereof. Bringing the an- imal in contact with the compound I, its salt or the veterinary composition of the invention means applying or administering it to the animal.

WO 2012/119984, WO 2016/168056, WO 2016/168058, and WO 2016/168059 describe active compounds of to some extent similar chemical structures. These compounds are mentioned to be useful for combating invertebrate pests.

Nevertheless, there remains a need for highly effective and versatile agents for combating in- vertebrate 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 dif- ferent 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 below, in the synthesis descriptions of the working examples, or by standard methods of organic chemistry which are known in the art. The substituents, variables and indices are as defined above for formula I, if not otherwise specified.

Compounds of formula I (la, lb, or lc) can be prepared by reacting a carboxylic acid of formula III, wherein X ^E is OH, or a carboxylic acid derivative of formula III·, wherein X ^E is a leaving group, preferably a halogen such as Cl or Br, or Ci-C ₆ -alkoxy, such as OCH3 or OC2H5, with an amine of formula II in an amidation reaction. The amidation reaction is preferably carried out with acid chlorides of formula III· or by prior transformation of carboxylic acids of formula III with oxalyl chloride [(COCI)2] or thionylchloride (SOCI2) to the corresponding acid chlorides of for- mula III·, followed by reaction with an amine of formula II. Suitable reaction conditions are de- scribed in the literature, e.g. in WO2004/22536. The reaction is preferrably carried out in the presence of an organic base such as, NEt3, N-ethyl-N,N-diisopropylamine (iP^NEt), pyridine, or 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. Suitable solvents are halogenated hydrocarbons such as, dichloromethane, chloroform, and chlorobenzene, or polar aprotic solvents such as tetrahydrofurane (THF), 1 ,4-dioxane, and N,N-dimethylformamide (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, prefer- ably 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 lla, based on Ilia, and an excess of lllb/lllc, based on llb/llc, resp.

Alternatively, amidation of the carboxylic acid III is carried out in the presence of a coupling re- agent. Suitable coupling reagents (activators) are known and are e.g. selected from carbodi- imides, such as N,N-dicyclohexylcarbodiimide (“DCC”) and N,N-diisopropylcarbodiimide (“DCI”), benzotriazole derivatives such as 1-[bis(dimethylamino)methylene]-1 H-1 ,2,3-triazolo[4,5-b]pyri- dinium 3-oxid hexafluorophosphate (“HATU”), 0-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluroni- um hexafluorophosphate (“HBTU”), and 1-[bis(dimethylamino)methylen]-5-chlorobenzotriazoli- um 3-oxide hexafluorophosphate (“HCTU”), or phosphonium-derived activators, such as (Ben- zotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (“BOP”), (benzotriazol- 1-yl-oxytripyrrolidinophosphonium hexafluorophosphate) (“Py-BOP”), bromotripyrrolidinophos- phonium hexafluorophosphate (“Py-BrOP”). Generally, the activator is used in excess. The ben- zotriazole and phosphonium coupling reagents are generally used in a basic medium. In turn, carboxylic acids of formula III can be prepared by hydrolyzation of an ester of formula III·, that is a compound of formula III wherein X ^E is Ci-C ₆ -alkoxy such as, e.g. OCH3, OC2H5, or OC(CH3)3. Hydrolyzation can be carried out under standard conditions known in the art, e.g. under aque- ous acidic conditions using e.g. hydrochloric acid, sulfuric acid (H2SO4) or trifluoroacetic acid (TFA), or under aqueous basic conditions using e.g. an alkali metal hydroxide, such as LiOH, NaOH or KOH. Amines of formula lla and carboxylic acids of formula lllb or lllc, respective!, are commercially available, or can be made as described in literature, or by standard methods of organic chemistry which are known in the art.

Compounds of formula G, that is compounds of formula I wherein U is S, can be prepared by reacting the corresponding oxocompound (U is O) with Lawesson's reagent (CAS 19172-47-5), see, e.g. Jesberger et al. Synthesis, 2003, 1929-1958 and references therein. Solvents such as HMPA or THF at an elevated temperature such as 60 °C to 100 °C can be used. Preferred reac- tion conditions are in THF at 65 °C.

Esters of formula Ilia', wherein X ^E is Ci-C ₆ -alkoxy such as OCH ₃ or OC ₂ H ₅ , can be obtained by reacting a compound of formula IV, wherein X ^Ar is halogen or 0S(=0) ₂ CF ₃ (“OTf”), with carbon monoxide in the presence of a palladium catalyst and an alcohol ROH, wherein R is Ci-C ₆ -alkyl. Suitabl

Alterantively, compounds of formula Ilia can be prepared by subjecting a compound of formula IV, that is a compound of formula IV wherein X ^Ar is Br, or I, to halogen-metal exchange followed by the in situ reaction of this metallated intermediate with carbon dioxide. Suitable reaction con- ditions are described in the literature, e.g. in W02009/132000, EP1582523. Suitable metalating agents are, e.g. iP^MgCI, iP^MgCI-LiCI (“TurboGrignard”), n-butyllithium, tert-butyllithium. Op- tionally, the reaction can be performed in the presence of an additional amine ligand such as, e.g., N,N,N',N'-tetramethylethylenediamine (“TMEDA”). Suitable solvents are ethers such as, e.g., THF, 2-methyltetrahydrofurane, diethyl ether (Et ₂ 0), or aliphatic hydrocarbons such as pentane, hexane, cyclohexane, or mixtures thereof. If desired, the obtained carboxylic acids of formula Ilia can be further transformed into the corresponding esters of formula Ilia', wherein X ^E is OR, in an esterification reaction. Esterification can be carried out under standard conditions known in the art, e.g. in the presence of an acid promotor such as e.g. H2SO4, and the corre- sponding alcohol ROH. Furthermore, it is also possible to transform a compound of formula IV, wherein X ^Ar is halogen or 0S(=0) ₂ CF ₃ , into an amide of formula la by reacting it with an amine of formula lla in the presence of a palladium catalyst and carbon monoxide, or a surrogate thereof such as e.g. MO(00) _Q , in an aminocarbonylation reaction.

Suitable reaction conditions are described in the literature, e.g. in WO2011/9749. Suitable palla- dium catalysts are, e.g., Pd(OAc) ₂ /PPh ₃ , Pd(OAc)/4,5-bis(diphenylphosphino)-9,9-dimethylxan- thene, dichloro[9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene]pal ladium(ll), [1 ,1 '-bis(diphe- nylphosphino)ferrocene]dichloropalladium(ll), (1 ,3-bis(diphenylphosphino)propane)palladium(ll) chloride, trans-bis(acetato)bis[o-(di-o-tolylphosphino)benzyl]dipallad ium(ll), and the like. The re- action is preferrably carried out in the presence of a base such as e.g. a tertiary amine like NEt3, iPr2NEt, N-methyl-N,N-dicyclohexylamine, 1 ,4-diaza-bicyclo[2.2.2]octane, or an amidine such as e.g. 1 ,8-diazabicyclo[5.4.0]undec-7-en, or an alkali metal carbonate such as e.g. Na ₂ C0 ₃ , K2CO3, CS2CO3, or an alkali metal phosphate such as e.g. K3PO4, and the like. Suitable sol- vents are aromatic hydrocarbons such as benzene, toluene, 0-, m-, and p-xylene, and the like, or polar aprotic solvents such as THF, 1 ,4-dioxane, DMF, N-methyl-2-pyrrolidon, and the like. The transformation is usually carried out at temperatures from 20 °C to 180 °C, preferably from 60 °C to 140 °C, and a carbon monoxide pressure from 0.5-20 bar, preferably from 1.0 to 7.0 bars. 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 lla, based on IV.

Amines of formula Mb can be prepared by reacting a compound of formula IV, wherein X ^Ar is halogen or 0S(=0) ₂ CF ₃ (“OTf”), in the presence of a palladium catalyst with an amine of for- mula R ⁵ NH2 in Buchwald-Hartwig Amination reaction. Suitable reaction conditions are reported in the literature (cf. WO2016/168059; P. Ruiz-Castillo and S. L. Buchwald Chem. Rev. 2016, 1 16, 12564-12649).

It is understood by a person skilled in the art that, in the presence of feasible T ¹ , T ² , R ³ , and X ^Ar , nucleophilic aromatic substitution between a compound of formula IV and an amine of for- mula R ⁵ NH2 may represent a practical alternative. Suitable reaction conditions are described in the literature (cf. W02010/100189).

Amines of formula lie can be prepared by reacting a compound of la-1 , that is a compound of formula la wherein R ⁶ is hydrogen, with a reducing agent such as, e.g. lithium aluminum hydride (LiAIFU), borane tetrahydrofuran complex (“BH3-THF”), borane dimethyl sulfide complex (BH ₃ -SMe ₂ ), in a reduction reaction. Suitable reaction conditions are described in the literature (cf. WO2016/96115, W02005/58301 , WO2014/202703). Suitable solvents are ethers such as THF, Et ₂ 0, tert-butylmethylether (TBME), or aromatic hydrocarbons such as benzene, toluene, 0-, m-, and p-xylene, or halogenated hydrocarbons such as, e.g. methylene chloride, chloro- form, 1 ,2-dichloroethane, or mixtures thereof.

Alternatively, compounds of formula lc, that is compounds of formula I wherein A is A2, and U is O, can be prepared by reductive amidation of a nitrile of formula lid in the presence of hydro- gen and a carboxylic acid derivative of formula III· wherein X ^E is a leaving group, preferably hal- og

The 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 Et ₂ 0, diisopropylether (DIPE), TBME, di- oxane, anisole, and THF, esters such as ethyl acetate, methyl acetate, isopropyl acetate, alco- hols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, and tert. -butanol, moreover DMF, and dimethylacetamide (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 bicarbonates, such as NaHC03, KHCO ₃ , moreover organic bases, e.g. tertiary amines, such as trimethylamine (NMe ₃ ), triethyla- mine (NEts), diisopropylethylamine, and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine, and DMAP, and also bicyclic amines. Particular preference is given to alkali metal bicarbonates and carbonates, such as NaHCOs or K2CO ₃ . The bases are generally employed in catalytic amounts; however, they can also be used in equimolar amounts, in ex- cess 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 heterogene- ous and homogeneous hydrogenation catalysts, but preferably refers to heterogeneous cata- lysts. 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 economical alternatives. In a preferred embodiment, the hy- drogenation catalyst is platinum or palladium on a carrier, Raney nickel, and Raney cobalt. Raney nickel is particularly preferred. The 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 at- mospheric pressure, which usually 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 III', based on lid.

In turn, compounds of formula lid can be obtained from compounds of formula IV as described in the literature, e.g. in W02005/21508, or

Compounds of formula I, wherein Z is N-R ^AZ and G is N(0) _n correspond to formula 1.1.

Such compounds can be prepared preferably via intermediates of formula IV.1

Transformation of group X ^Ar to groups A is effected as outlined above for general formulae lib, lie, Ilia, and IV.

Compounds of formula IV.1 can be prepared by reacting an amide of formula 5a, or 5a', or a mixture of the two isomers, in a condensation reaction. Suitable reaction conditions are de- scribed in the literature, e.g. in WO 2016/100515, or in WO 2007/102059. The reaction is gener- ally performed in the presence of an acid promoter such as, e.g. acetic acid, trifluoroacetic acid, toluene-4-sulfonic acid, hydrochloric acid, sulfuric acid, and the like. Suitable solvents are car- boxylic acids such as acetic acid, propanoic acid, and the like, or aromatic hydrocarbons such as benzene, toluene, 0-, m , and p-xylene, and the like, or halogenated hydrocarbons such as methylene chloride, chloroform, 1 ,2-dichloroethane, or po-lar aprotic solvents such as 1 ,4-diox- ane, acetonitrile, DMF, tetrahydrofuran, or alcohols such as methanol, ethanol, and the like, or water, and it is also possible to use mixtures of the solvents mentioned. If desired, water, which is formed in the course of the reaction, can be continously removed by means of a Dean-Stark trap. The transformation is usually carried out at temperatures from 40°C to 200°C, preferably from 60°C to 140°C.

In turn, amides of formula 5a and 5a' can be prepared by reacting a diamine of formula 6a with a carboxylic acid of formula 7 in an amidation reaction under the same reaction conditions as descrided above for the formation of compounds of formula I. Compounds of formula 7 are known from WO 2016/168059.

Compounds of formula 6a can be prepared by reduction of a nitro compound of formula 8a un- der conditions known in the art, e.g. in WO 2015/79251 , or in WO 2014/140075.

Compounds of formula 8a can be prepared by reacting halogen-nitro compounds of formula 9, wherein Y ^Ar is halogen, preferably F or Cl, with amines of formula FhNR ⁴² in an nucleophilic aro- matic substitution reaction, under conditions known in the art, e.g. in WO 2012/1 19984. In turn, compounds of formula 9 are commercially available, or can be made by standard methods of organic chemistry which are known in the art.

N-oxides of the compounds of formula I can be prepared by oxidation of compounds I accord- ing to standard methods of preparing heteroaromatic N-oxides, e.g. by the method described in Journal of Organometallic Chemistry 1989, 370, 17-31 .

Compounds of formula I, wherein Z is N(0) _n and G is N-R ^AZ correspond to formula 1.2.

Such compounds can be prepared from halogen-nitro compounds of formula 10, wherein Y ^Ar is halogen, preferably F or Cl, in analogy as described above for compounds of formula 1.1.

10

Compounds of formula 10 are commercially available, or can be made by standard methods of organic chemistry which are known in the art.

Compounds of formula I, wherein Z is O and G is N(0) _n correspond to formula 1.3.

Such compounds can be prepared preferably via intermediates of formula IV.3

Transformation of group X ^Ar to groups A is effected as outlined above for general formulae lib, lie, Ilia, and IV.

Compounds of formula IV.3 can be prepared by reacting an amide of formula 5c in a conden- sation reaction.

Suitable reaction conditions are reported in literature, e.g. in W02009/63061 , in

US2007/238726, or in US2008/214601. The reaction is generally performed in the presence of an activating/dehydrating agent such as, e.g. Bronstedt acids like para-toluenesulfonic acid, methanesulfonic acid, pyridinium para-toluenesulfonate, trifluoroacetic acid, acetic acid, propi- onic acid, hydrogenchloride, sulfuric acid, and the like, or phosphoric acid derivatives such as, P ₂ O ₅ , trichlorophosphate, polyphosphoric acid, and the like, or activated organophosphines that are formed in situ by combining reagents such as, e.g. PPh3/diisopropyl azodicarboxylate, PPhi3/diethyl azodicarboxylate, PPh3/hexachloroethane, and the like. Suitable solvents are aro- matic hydrocarbons such as benzene, toluene, 0-, m-, and p-xylene, and the like, or polar apro- tic solvents such as tetrahydrofuran, 1 ,4-dioxane, acetonitrile, DMF, or halogenated hydrocar- bons such as methylene chloride, chloroform, 1 ,2-dichloroethane, 1 ,2-dichlorobenzene, and the like, and it is also possible to use mixtures of the solvents mentioned. In turn, amides of formula 5c can be prepared by reacting a amine of formula 6c with a carboxylic acid of formula 7 in an amidation reaction under the same reaction conditions as descrided above for the formation of compounds of formula I. Compounds of formula 6c can be be prepared by reduction of a nitro compound of formula 8c under conditions known in the art, e.g. in WO 2015/79251 , or in WO

2014/140075.

Compounds of formula 8c can be prepared by reacting halogen-nitro compounds of formula 9, wherein Y ^Ar is halogen, preferably F or Cl, in an nucleophilic aromatic substitution reaction un- der conditions known in the art, e.g. in US4623650, or in WO 2014/66490. Alternatively, corn- pounds of formula 8c can be prepared by reacting a phenol of formula 11 in a nitration reaction under conditions known in the art,

Compounds of formula 9 and 11 , respectively, are commercially available, or can be made by standard methods of organic chemistry which are known in the art.

Compounds of formula I, wherein Z is N(0) _n and G is O correspond to formula I.4.

Such compounds can be prepared from halogen-nitro compounds of formula 10, wherein Y ^Ar is halogen, preferably F or Cl, or from phenols of formula 12, respectively, in analogy as described above for compounds of formula 1.3.

Compounds of formula 10, and 12, respectively, are commercially available, or can be made by standard methods of organic chemistry which are known in the art.

Compounds of formula I, wherein Z is S and G is N(0) _n correspond to formula 1.5.

Such compounds can be prepared preferably via intermediates of formula IV.5

Transformation of group X ^Ar to groups A is effected as outlined above for general formulae Mb, lie, Ilia, and IV.

Compounds of formula IV.5 can be prepared by reacting an acid of formula 7 with an amino thiol of formula 13 in a condensation reaction. Suitable reaction conditions are reported in the literature, e.g. in WO 2015/153554, or in US 2005/250820. The reaction is generally carried out in the presence of an activating/dehydrating agent such as, e.g. phosphonic anhydrides like 2,4,6-tripropyl-1 ,3,5,2,4,6-trioxatriphos- phorinane-2, 4, 6-trioxide (CAS number: 68957-94-8), or polyphosphoric acid, or phosphorous trichloride, or organophosphites like triphenyl phosphite, or P2O5, or methanesulfonic acid, and the like. If phosphonic anhydrides are used as activating agens, an amine base may be em- ployed in the reaction such as, e.g. a tertiary amine like NEt3, N,N-diisopropylethylamine, and the like. Suitable solvents are aromatic hydrocarbons such as toluene, 0-, m-, and p-xylene, and the like, or polar aprotic solvents such as tetrahydrofuran, ethyl acetate, DMF, and the like, and it is also possible to use mixtures of the solvents mentioned. Alternatively, it is also possible to obtain compounds of formula IV.5 from acids of formula 7 and amino thiols of formula 6e over a 2 steps sequence involving an amidaion reaction followed by a condensation reaction, ana- loguously as described for the synthesis of compounds IV.1 or IV.3.

Compounds of formula 6e can be be prepared by reduction of a nitro compound of formula 8e under conditions kno

Compounds of formula 8e can be prepared by reacting halogen-nitro compounds of formula 9, wherein Y ^Ar is halogen, preferably F or Cl, in a nucleophilic aromatic substitution reaction under conditions known in the art, e.g. in W02014/190199. Compounds of formula 9 are commercially available, or can be made by standard methods of organic chemistry which are known in the art. Compounds of formula I, wherein Z is N(0) _n and G is S correspond to formula I.6.

Such compounds can be prepared from halogen-nitro compounds of formula 10, wherein Y ^Ar is halogen, preferably F or Cl, in analogy as described above for compounds of formula 1.5. Com- pounds of formula 10 are commercially available, or can be made by standard methods of or- ganic chemistry which are known in the art.

Compounds of formula I, wherein Z is NR ^AZ and G is CR ^A correspond to formula 1.7.

Such compounds can be prepared preferably via intermediates of formula IV.7

Transformation of group X ^Ar to groups A is effected as outlined above for general formulae Mb, Me, Mia, and IV.

Compounds of formula IV.7 can be prepared by reacting a ketone of formula 13 with a hydra- zine derivative of formula 14 in a Fischer indole synthesis reaction.

Suitable reaction conditions are described in the literature, e.g. in WO2005/13985. The reaction is generally performed in the presence of an acid such as, e.g. carbocylic acids like acetic acid, trifluoroacetic acid, and the like, or mineral acids like hydrochloric acid, sulfuric acid, phosphoric acid, and the like, or sulfonic acids like methanesulfonic acid, toluene-4-sulfonic acid, and the like. Suitable solvents are alcohols such as, e.g. methanol, ethanol, isopropanol, and the like, or aromatic hydrocarbons such as e.g. benzene, toluene, 0-, m-, and p-xylene, and the like, or car- boxylic acids such as acetic acid, propionic acid, and the like, or ethers such as 1 ,4-dioxane, and the like. The transformation is usually carried out at temperatures from 20 °C to 180 °C, preferably from 60 °C to 140 °C.

Ketones of formula 13 can be prepared by reacting a Weinreb amide of formula 16 with the corresponding organolithium or organomagnesium compound of formula M-CFhR ⁴ , wherein M is Li, or MgX (X = Cl, 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 ₂ 0, DIPE, TBME, or or aliphatic hydrocarbons such as pentane, hexane, cyclohexane, petrol ether, or mixtures thereof. The transformation is usually carried out at temperatures from -100 °C to 50 °C, preferably from -78 °C to 25 °C. Weinreb amides of formula 16, in turn, can be prepared by reacting a carboxylic acid of formula 7, wherein X ^E is OH, or a carboxylic acid derivative of formula 7', wherein X ^E is a leaving group, preferably a halogen such as Cl or Br, or Ci-C ₆ -alkoxy, such as OCH3 or OC2H5, with the Weinreb amine of formula CH ₃ NH(OCH ₃ ) in an amidation-type 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 7', in the presence of a Lewis acid activator 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, 0-, m-, and p-xylene, or polar aprotic solvents such as THF, Et ₂ 0, or aliphatic hydrocarbons such as pentane, hexane, cyclohexane, petrol ether, or mixtures thereof. Alterna- tively, Weinreb amides of formula 16 can also be obtained by reacting acyl chlorides of formula T or carboxylic acids of formula 7 respectively, with the Weinreb amine CH ₃ NH(OCH ₃ ) or its hy- drochloride salt (CAS 6638-79-5) under analogous amidation reaction conditions as described above, e.g. for the synthesis of compounds of formula I.

Hydrazine derivatives of formula 14 are commercially available, or can be prepared from the corresponding anilines of formula 15 via a N-nitrosylation/reduction sequence.

Suitable reaction conditions are described in the literature, e.g. in US 5,023,255, and generally known in the art. Anilines of formula 15 are commercially available, or can be made by standard methods of organic chemistry which are known in the art.

Compounds of formula I, wherein Z is CR ^A and G is NR ^AZ correspond to formula 1.8.

Such compounds can be prepared preferably via intermediates of formula IV.8

Transformation of group X ^Ar to groups A is effected as outlined above for general formulae lib, lie, Ilia, and IV.

Compounds of formula IV.8 can be prepared from hydrazines of formula 17, or anilines of for- mula 18, respectively, in analogy as described above for compounds of formula 1.7.

Compounds of formula 18 are commercially available, or can be made by standard methods of organic chemistry which are known in the art. Compounds of formula I, wherein Z is O, S(0) _m , NR ^AZ and G is CR ^A correspond to formula 1.9.

Such compounds can be prepared preferably via intermediates of formula IV.9

Transformation of group X ^Ar to groups A is effected as outlined above for general formulae Mb, Me, Mia, and IV.

Compounds of formula 1.9 or IV.9, respectively, can be prepared by cyclization of an alkyne of formula 19, wherein Q ^Ar is X ^Ar or A, by reacting it with a suitable electrophilic reagent, or in the presence of a suitable electrophilic promotor, or catalyst.

Suitable reaction conditions are described in the literature, e.g. in M. Michalska, K. Grela, Syn- lett, 2016, p. 599-603 (R ^A = H), in D. Yue, R. C. Larock, Journal of Organic Chemistry, 2002, vol. 67, p. 1905-1909 (R ^A = I), or in M. Nakamura, L. Ilies, S. Otsubo, E. Nakamura, Organic Letters, 2006, vol. 8, p. 2803-2805 (R ^A = allyl).

It will be understood by a person skilled in the art that the compounds of formula 1.9 or IV.9, wherein R ^A is halogen, such as e.g. Br, or I, can be transformed further into other compounds of formula 1.9 or IV.9, respectively, by reacting them with an appropriate transmetallating agent R ^A M such as, e.g. R ^A ZnCI, R ^A ZnBr, (R ^A ) ₂ Zn, R ^A Sn(alkyl) ₃ , (R ^A ) ₄ Sn, R ^A B(OH) ₂ , R ^A B(0-alkyl) ₂ , R ^A B(alkyl)2, AI(R ^A ) ₃ , and the like in the presence of a metal catalyst, preferably a palladium cata- lyst, in a cross coupling reaction. Suitable reaction conditions are described in the literature (cf. A. de Meijere et al.,“Metal-Catalyzed Cross-Coupling Reactions and More”, Wiley-VCH, 2014, and references therein).

Compounds of formula 19, in turn, can be prepared by reacting a terminal alkyne of formula 20 with an arene of formula 21 in a Sonogashira or a Sonogashira-type cross-coupling reaction.

Suitable reaction conditions are described in literature (cf. A. de Meijere et al.,“Metal-Cata- lyzed Cross-Coupling Reactions and More”, Wiley-VCH, 2014). The reaction is generally carried out in the presence of a palladium catalyst such as tetrakis(triphenylphosphine)palladium(0), bis(triphenylphosphine)palladium(ll) dichloride, palladium(ll) acetate, and in the presence of a base such as an amine base like NEt3, iP^NEt, diisopropylamine, diethylamine, piperidine, pyr- rolidine, n-butylamine, or alkali metal carbonates, such as K2CO ₃ , CS2CO ₃ . The base is gener- ally used in equimolar amounts or in excess, but it can also be used as the solvent if appropri- ate. Preferrably, a copper salt is employed in the reaction such as CuCI, CuBr, and Cul. Amine bases may be used as the only solvent, or in combination with an additional solvent. Suitable additional solvents are polar aprotic solvents such as THF, DMF, acetonitrile, or aromatic hydro- carbons such as benzene, toluene, 0-, m-, and p-xylene, or mixtures thereof.

Compounds of formula 21 are commercially available, or can be made by standard methods of organic chemistry which are known in the art.

Alkynes of formula 20 can be prepared by reacting an aldehyde of formula 22 with dimethyl (1 - diazo-2-oxopropyl)phosphonate (CAS 90965-06-3) in an Ohira-Bestmann reaction.

20

Suitable reaction conditions are described in literature (cf. H.-J. Bestmann et al., Synlett, 1996, 521 -522; WO2017/37221 ). The reaction is generally carried out in the presence of a base such as alkali metal carbonates like K2CO ₃ . Suitable solvents are alcohols such as methanol. The transformation is usually carried out at temperatures from -20 °C to 60 °C, preferably from 0 °C to 25 °C. Alternatively, alkynes of formula 5a', can be prepared by reacting an aldehyde of for- mula 12 with dimethyl diazomethylphosphonate (CAS 27491 -70-9) in a Seyferth-Gilbert reac- tion. Suitable reaction conditions are described in literature (cf. Y.Wu et al. Eur. J. Org. Chem. 2001 , 3779-3788; B.M.Trost et al. JACS 1996, 1 18, 5146-5147). The reaction is generally car- ried out in the presence of a base such as an alkali metal alcoholate like potassium tert-bu- tylate, or an alkali metal amide such as sodium hexamethyldisilazane (NaN[Si(CH3)3]2), potas- sium hexamethyldisilazane (KN[Si(CH3)3]2), lithium diidopropylamide (“LDA”), or an organolith- ium base such as n-butyllithium. Suitable solvents are ethers such as THF, or aliphatic hydro- carbons such as pentane, hexane, cyclohexane, and petrol ether, or mixtures thereof.

Aldehydes of formula of formula 22 are known from WO 2016/168059.

Compounds of formula I, wherein G is O, S(0) _m , NR ^AZ and Z is CR ^A correspond to formula 1.10

Such compounds can be prepared preferably via intermediates of formula IV.10

Transformation of group X ^Ar to groups A is effected as outlined above for general formulae lib, lie, Ilia, and IV.

Compounds of formula 1.10 or IV.10, respectively, can be prepared from compounds of formula 23, in analogy as described above for compounds of formula 1.9.

Compounds of formula 23 are commercially available, or can be made by standard methods of organic chemistry which are known in the art.

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 pre- pared by derivatization of other compounds I or the respective precursor or by customary modi- fications of the synthesis routes described. E.g., in individual cases, certain compounds of for- mula I can advantageously be prepared from other compounds of formula I by derivatization, e.g. by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxida- tion and the like, 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, sep- arating 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 hal- ogen - 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 flu orine, 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 al- kyl 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-C ₄ -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, fre- quently 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 corn- prising 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 alk oxy 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-C ₆ -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, where- in the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or io- dine.

The term "alkenyl" as used herein denotes in each case a singly unsaturated hydrocarbon rad- ical 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 rad- ical 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 (C-C3H5), cyclobutyl (C-C4H7), cyclopentyl (c- C5H9), cyclohexyl (c-CeHn), 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 ha- ving usually from 3 to 10, e.g. 3 or 4 or from 5 to 10 carbon atoms, preferably from 3- to 8 car- bon 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 C-i-Cs-alkyl group or a Ci-C ₄ -alkyl group, in particular a meth- ylene 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" includes monocyclic 5- or 6-membered heteroaromatic radicals comprising as ring members 1 , 2, or 3 heteroatoms selected from N, O and S. Examples of 5- or 6-mem- bered 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, isoxazo- lyl, i.e. 3-, 4- and 5-isoxazolyl, thiazolyl, i.e. 2-, 3- and 5-thiazolyl, isothiazolyl, 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-thiadiazol-5-yl, 1 ,2,4-thiadia- zol-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 de- fined above which are bound via a Ci-C ₄ -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 par- ticular 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. The trans-isomers I.B and I.D are usually present as a 1 :1 mixture.

In one particularly preferred embodiment of the invention, the method comprises step of con- tacting 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, which may be part of a mixture of I.B and I.D.

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 Cl or Br.

In one embodiment R ^1a and R ^1b are both halogen, such as Cl or Br, preferably Cl.

In another embodiment R ^1a is H, and R ^1b is halogen, such as Cl or Br.

R ^2a is preferably selected from F, Cl, Br, CF ₃ , and OCF ₃ .

R ^2b and R ^2c are independently preferably selected from H, F, Cl, Br, CF ₃ , and OCF ₃ .

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 (“Ring A”) bearing the R ^2a , R ^2b and R ^2c moieties.

Table A

Groups A-8, A-9, A-10, A-1 1 , A-18, A-20, A-26, and A-32 are more preferred patterns in for- mula I compounds. A-9 is particularly preferred.

In one preferred embodiment the T ¹ and T ² containing ring (“Ring T”) represents a group D1 :

wherein

R ³ , R ⁴¹ , and R ⁴² are independently preferably H, halogen, CN, OH, NH2, Ci-C4-alkyl, cyclopro- pyl, or Ci-C4-haloalkyl.

More preferably R ⁴¹ and R ⁴² are independently H, or alkyl such as CH ₃ , or halomethyl such as CF ₃ , or halogen such as Cl or F, and R ³ is H.

More preferably one of R ⁴¹ and R ⁴² is a halogen such as Cl or F, or alkyl such as CH ₃ , and R ³ is H.

Particularly R ³ , R ⁴² are H, and R ⁴¹ is F, Cl, or CH ₃ .

In another embodiment R ⁴¹ is Cl, and R ³ , R ⁴² , and R ⁴³ are H.

In another embodiment the T ¹ and T ² containing ring (“Ring T”) represents a group D2:

wherein

R ³ and R ⁴¹ are independently preferably H, halogen, CN, Ci-C4-alkyl, cyclopropyl, or C1-C4- haloalkyl; more preferably H, CF ₃ , CH ₃ , Br, Cl, or F. Particularly R ³ is H, and R ⁴¹ is H, CF ₃ , CH ₃ , Cl, or F; most preferred Cl.

In another embodiment the T ¹ and T ² containing ring (“Ring T”) represents a group D3:

wherein

R ³ , and R ⁴² are independently preferably H, halogen, CN, Ci-C4-alkyl, cyclopropyl, or C1-C4- haloalkyl; more preferably H, CF ₃ , CH ₃ , Br, Cl, or F. Particularly R ³ is H, and R ⁴² is H, CF ₃ , CH ₃ , Cl, or F, most preferred Cl, or F. The bicyclic heterocycle formed by groups Z, G, T ¹ and T ² and the connecting carbon atoms are preferably selected from groups HE1 , HE2, HE3, HE4, HE5, HE6, HE7, and HE8,

wherein # marks the bond to the cyclopropyl ring, and

R ⁴¹ and R ⁴² independently from one another represent a group R ⁴ , which preferably is H, halo- gen, Ci-C ₄ -alkyl, Ci-C3-haloalkyl.

R ^AZ is preferably H, Ci-C ₄ -alkyl, Ci-C ₄ -haloalkyl, C2-C ₄ -alkenyl, C2-C ₄ -alkynyl, and C3-C6-cyclo- alkyl which is unsubstituted or partially or fully substituted with halogen or CN, more preferably

H, Ci-C ₄ -alkyl, and Ci-C ₄ -alkynyl; particularly H, CH ₃ , C2H ₅ , and propargyl.

R ³ preferably is H, halogen, Ci-C ₄ -alkyl, Ci-C3-haloalkyl; particularly H.

HE1 is particularly preferred.

Preferred Z are NR ^AZ , O, and S. Most preferred Z is NR ^AZ .

Preferred G is N or CR ⁴ , more preferably N.

Formula I, wherein HE is selected from HE1 , HE2, HE3, and HE4 resp., is formula I.H1 , I.H2,

I.H3, and I.H4 resp.

In one preferred embodiment A is A1 .

In another embodiment A is A2, wherein the index n is preferably 0 or 1 . R ⁵ is preferably H, or Ci-C4-alkyl such as CH ₃ or CH2CH ₃ .

R ⁶ is preferably Ci-C ₆ -alkyl, Ci-C ₄ -haloalkyl, C3-C6-cycloalkyl, or phenyl, which rings are un- substituted or substituted with 1 , 2, or 3 substituents R ^a which are preferably halogen, CN, CH3, or C(=S)N(R ³¹ )R ³² , wherein R ³¹ and R ³² , are H, or Ci-C4-alkyl, particularly H.

In a preferred embodiment R ⁶ is benzyl or phenyl which are unsubstituted or substituted with halogen, and Ci-C4-haloalkyl. Particularly preferred meaning for R ⁶ is a group P, wherein # is the bond to the amide-N:

P

and R ⁶¹ , R ⁶² , and R ⁶³ are halogen or Ci-C4-haloalkyl.

In a particularly preferred embodiment R ⁶¹ is Br, R ⁶² , is CF ₃ , and R ⁶³ is CF(CF ₃ )2.

In a particularly preferred embodiment n is 0. Particularly preferred is each one of the following combinations of R ⁶¹ , R ⁶² , and R ⁶³ wherein each line of Table P denotes a substitution pattern of the phenyl ring (“P”) bearing the R ⁶¹ , R ⁶² , and R ⁶³ moieties, wherein n is 0.

Table P

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. Preferred embodiments relate to each of following compounds of formula I, wherein the varia- bles 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 corn- piled in the tables below, which compounds correspond to formulae I.H1 ^* , I.H2 ^* , I.H3 ^* , and I.H4 ^* , 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.H1 ^* in which R ^AZ is H, R ⁶ is C-C ₃ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 2 : Compounds of formula I.H1 ^* in which R ^AZ is CH ₃ , R ⁶ is C-C ₃ H ₅ , and the other varia- bles for a compound correspond in each case to one row of Table B

Table 3 : Compounds of formula I.H1 ^* in which R ^AZ is C ₂ H ₅ , R ⁶ is C-C ₃ H ₅ , and the other varia- bles for a compound correspond in each case to one row of Table B

Table 4 : Compounds of formula I.H1 ^* in which R ^AZ is CH ₂ CH=CH ₂ , R ⁶ is C-C ₃ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 5 : Compounds of formula I.H1 ^* in which R ^AZ is CH ₂ CºCH, R ⁶ is C-C ₃ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 6 : Compounds of formula I.H1 ^* in which R ^AZ is C-C ₃ H ₅ , R ⁶ is C-C ₃ H ₅ , and the other vari- ables for a compound correspond in each case to one row of Table B

Table 7 : Compounds of formula I.H2 ^* in which R ^AZ is H, R ⁶ is C-C ₃ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 8 : Compounds of formula I.H2 ^* in which R ^AZ is CH ₃ , R ⁶ is C-C ₃ H ₅ , and the other varia- bles for a compound correspond in each case to one row of Table B

Table 9 : Compounds of formula I.H2 ^* in which R ^AZ is C ₂ H ₅ , R ⁶ is C-C ₃ H ₅ , and the other varia- bles for a compound correspond in each case to one row of Table B

Table 10 : Compounds of formula I.H2 ^* in which R ^AZ is CH ₂ CH=CH ₂ , R ⁶ is C-C ₃ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 1 1 : Compounds of formula I.H2 ^* in which R ^AZ is CH ₂ CºCH, R ⁶ is C-C ₃ H ₅ , and the other variables for a compound correspond in each case to one row of Table B Table 12 : Compounds of formula I.H2 ^* in which R ^AZ is C-C3H5, R ⁶ is C-C3H5, and the other variables for a compound correspond in each case to one row of Table B

Table 13 : Compounds of formula I.H3 ^* in which R ^AZ is H, R ⁶ is C-C3H5, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 14 : Compounds of formula I.H3 ^* in which R ^AZ is CH3, R ⁶ is C-C3H5, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 15 : Compounds of formula I.H3 ^* in which R ^AZ is C2H5, R ⁶ is C-C3H5, and the other vari- ables for a compound correspond in each case to one row of T able B

Table 16 : Compounds of formula I.H3 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is C-C3H5, and the other variables for a compound correspond in each case to one row of Table B

Table 17 : Compounds of formula I.H3 ^* in which R ^AZ is CH2CºCH, R ⁶ is C-C3H5, and the other variables for a compound correspond in each case to one row of Table B

Table 18 : Compounds of formula I.H3 ^* in which R ^AZ is C-C3H5, R ⁶ is C-C3H5, and the other variables for a compound correspond in each case to one row of Table B

Table 19 : Compounds of formula I.H4 ^* in which R ^AZ is H, R ⁶ is C-C3H5, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 20 : Compounds of formula I.H4 ^* in which R ^AZ is CH3, R ⁶ is C-C3H5, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 21 : Compounds of formula I.H4 ^* in which R ^AZ is C2H5, R ⁶ is C-C3H5, and the other vari- ables for a compound correspond in each case to one row of T able B

Table 22 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is C-C3H5, and the other variables for a compound correspond in each case to one row of Table B

Table 23 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CºCH, R ⁶ is C-C3H5, and the other variables for a compound correspond in each case to one row of Table B

Table 24 : Compounds of formula I.H4 ^* in which R ^AZ is C-C3H5, R ⁶ is C-C3H5, and the other variables for a compound correspond in each case to one row of Table B

Table 25 : Compounds of formula I.H1 ^* in which R ^AZ is H, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 26 : Compounds of formula I.H1 ^* in which R ^AZ is CH3, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 27 : Compounds of formula I.H1 ^* in which R ^AZ is C2H5, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 28 : Compounds of formula I.H1 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 29 : Compounds of formula I.H1 ^* in which R ^AZ is CH2CºCH, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 30 : Compounds of formula I.H1 ^* in which R ^AZ is C-C3H5, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 31 : Compounds of formula I.H2 ^* in which R ^AZ is H, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 32 : Compounds of formula I.H2 ^* in which R ^AZ is CH3, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 33 : Compounds of formula I.H2 ^* in which R ^AZ is C2H5, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B Table 34 : Compounds of formula I.H2 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 35 : Compounds of formula I.H2 ^* in which R ^AZ is CH2CºCH, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 36 : Compounds of formula I.H2 ^* in which R ^AZ is C-C3H5, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 37 : Compounds of formula I.H3 ^* in which R ^AZ is H, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 38 : Compounds of formula I.H3 ^* in which R ^AZ is CH3, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 39 : Compounds of formula I.H3 ^* in which R ^AZ is C2H5, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 40 : Compounds of formula I.H3 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 41 : Compounds of formula I.H3 ^* in which R ^AZ is CH2CºCH, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 42 : Compounds of formula I.H3 ^* in which R ^AZ is C-C3H5, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 43 : Compounds of formula I.H4 ^* in which R ^AZ is H, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 44 : Compounds of formula I.H4 ^* in which R ^AZ is CH3, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 45 : Compounds of formula I.H4 ^* in which R ^AZ is C2H5, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 46 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 47 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CºCH, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 48 : Compounds of formula I.H4 ^* in which R ^AZ is C-C3H5, R ⁶ is I-CN-C-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 49 : Compounds of formula I.H1 ^* in which R ^AZ is H, R ⁶ is C-C4H7, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 50 : Compounds of formula I.H1 ^* in which R ^AZ is CH3, R ⁶ is C-C4H7, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 51 : Compounds of formula I.H1 ^* in which R ^AZ is C2H5, R ⁶ is C-C4H7, and the other vari- ables for a compound correspond in each case to one row of Table B

Table 52 : Compounds of formula I.H1 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is C-C4H7, and the other variables for a compound correspond in each case to one row of Table B

Table 53 : Compounds of formula I.H1 ^* in which R ^AZ is CH2CºCH, R ⁶ is C-C4H7, and the other variables for a compound correspond in each case to one row of Table B

Table 54 : Compounds of formula I.H1 ^* in which R ^AZ is C-C3H5, R ⁶ is C-C4H7, and the other variables for a compound correspond in each case to one row of Table B

Table 55 : Compounds of formula I.H2 ^* in which R ^AZ is H, R ⁶ is C-C4H7, and the other varia- bles for a compound correspond in each case to one row of Table B Table 56 : Compounds of formula I.H2 ^* in which R ^AZ is CH3, R ⁶ is C-C4H7, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 57 : Compounds of formula I.H2 ^* in which R ^AZ is C2H5, R ⁶ is C-C4H7, and the other vari- ables for a compound correspond in each case to one row of T able B

Table 58 : Compounds of formula I.H2 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is C-C4H7, and the other variables for a compound correspond in each case to one row of Table B

Table 59 : Compounds of formula I.H2 ^* in which R ^AZ is CH2CºCH, R ⁶ is C-C4H7, and the other variables for a compound correspond in each case to one row of Table B

Table 60 : Compounds of formula I.H2 ^* in which R ^AZ is C-C3H5, R ⁶ is C-C4H7, and the other variables for a compound correspond in each case to one row of Table B

Table 61 : Compounds of formula I.H3 ^* in which R ^AZ is H, R ⁶ is C-C4H7, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 62 : Compounds of formula I.H3 ^* in which R ^AZ is CH3, R ⁶ is C-C4H7, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 63 : Compounds of formula I.H3 ^* in which R ^AZ is C2H5, R ⁶ is C-C4H7, and the other vari- ables for a compound correspond in each case to one row of T able B

Table 64 : Compounds of formula I.H3 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is C-C4H7, and the other variables for a compound correspond in each case to one row of Table B

Table 65 : Compounds of formula I.H3 ^* in which R ^AZ is CH2CºCH, R ⁶ is C-C4H7, and the other variables for a compound correspond in each case to one row of Table B

Table 66 : Compounds of formula I.H3 ^* in which R ^AZ is C-C3H5, R ⁶ is C-C4H7, and the other variables for a compound correspond in each case to one row of Table B

Table 67 : Compounds of formula I.H4 ^* in which R ^AZ is H, R ⁶ is C-C4H7, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 68 : Compounds of formula I.H4 ^* in which R ^AZ is CH3, R ⁶ is C-C4H7, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 69 : Compounds of formula I.H4 ^* in which R ^AZ is C2H5, R ⁶ is C-C4H7, and the other vari- ables for a compound correspond in each case to one row of T able B

Table 70 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is C-C4H7, and the other variables for a compound correspond in each case to one row of Table B

Table 71 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CºCH, R ⁶ is C-C4H7, and the other variables for a compound correspond in each case to one row of Table B

Table 72 : Compounds of formula I.H4 ^* in which R ^AZ is C-C3H5, R ⁶ is C-C4H7, and the other variables for a compound correspond in each case to one row of Table B

Table 73 : Compounds of formula I.H1 ^* in which R ^AZ is H, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 74 : Compounds of formula I.H1 ^* in which R ^AZ is CH3, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 75 : Compounds of formula I.H1 ^* in which R ^AZ is C2H5, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 76 : Compounds of formula I.H1 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 77 : Compounds of formula I.H1 ^* in which R ^AZ is CH2CºCH, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B Table 78 : Compounds of formula I.H1 ^* in which R ^AZ is C-C3H5, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 79 : Compounds of formula I.H2 ^* in which R ^AZ is H, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 80 : Compounds of formula I.H2 ^* in which R ^AZ is CH3, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 81 : Compounds of formula I.H2 ^* in which R ^AZ is C2H5, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 82 : Compounds of formula I.H2 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 83 : Compounds of formula I.H2 ^* in which R ^AZ is CH2CºCH, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 84 : Compounds of formula I.H2 ^* in which R ^AZ is C-C3H5, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 85 : Compounds of formula I.H3 ^* in which R ^AZ is H, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 86 : Compounds of formula I.H3 ^* in which R ^AZ is CH3, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 87 : Compounds of formula I.H3 ^* in which R ^AZ is C2H5, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 88 : Compounds of formula I.H3 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is 3,3-F2-c-C4H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 89 : Compounds of formula I.H3 ^* in which R ^AZ is CH2CºCH, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 90 : Compounds of formula I.H3 ^* in which R ^AZ is C-C3H5, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 91 : Compounds of formula I.H4 ^* in which R ^AZ is H, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 92 : Compounds of formula I.H4 ^* in which R ^AZ is CH3, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 93 : Compounds of formula I.H4 ^* in which R ^AZ is C2H5, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 94 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 95 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CºCH, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 96 : Compounds of formula I.H4 ^* in which R ^AZ is C-C3H5, R ⁶ is 3,3-F ₂ -c-C ₄ H ₅ , and the other variables for a compound correspond in each case to one row of Table B

Table 97 : Compounds of formula I.H1 ^* in which R ^AZ is H, R ⁶ is n-butyl, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 98 : Compounds of formula I.H1 ^* in which R ^AZ is CH3, R ⁶ is n-butyl, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 99 : Compounds of formula I.H1 ^* in which R ^AZ is C2H5, R ⁶ is n-butyl, and the other vari- ables for a compound correspond in each case to one row of T able B Table 100 : Compounds of formula I.H1 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is n-butyl, and the other variables for a compound correspond in each case to one row of Table B

Table 101 : Compounds of formula I.H1 ^* in which R ^AZ is CH2CºCH, R ⁶ is n-butyl, and the other variables for a compound correspond in each case to one row of Table B

Table 102 : Compounds of formula I.H1 ^* in which R ^AZ is C-C3H5, R ⁶ is n-butyl, and the other variables for a compound correspond in each case to one row of Table B

Table 103 : Compounds of formula I.H2 ^* in which R ^AZ is H, R ⁶ is n-butyl, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 104 : Compounds of formula I.H2 ^* in which R ^AZ is CH3, R ⁶ is n-butyl, and the other vari- ables for a compound correspond in each case to one row of T able B

Table 105 : Compounds of formula I.H2 ^* in which R ^AZ is C2H5, R ⁶ is n-butyl, and the other var- iables for a compound correspond in each case to one row of Table B

Table 106 : Compounds of formula I.H2 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is n-butyl, and the other variables for a compound correspond in each case to one row of Table B

Table 107 : Compounds of formula I.H2 ^* in which R ^AZ is CH2CºCH, R ⁶ is n-butyl, and the other variables for a compound correspond in each case to one row of Table B

Table 108 : Compounds of formula I.H2 ^* in which R ^AZ is C-C3H5, R ⁶ is n-butyl, and the other variables for a compound correspond in each case to one row of Table B

Table 109 : Compounds of formula I.H3 ^* in which R ^AZ is H, R ⁶ is n-butyl, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 110 : Compounds of formula I.H3 ^* in which R ^AZ is CH3, R ⁶ is n-butyl, and the other vari- ables for a compound correspond in each case to one row of T able B

Table 11 1 : Compounds of formula I.H3 ^* in which R ^AZ is C2H5, R ⁶ is n-butyl, and the other var- iables for a compound correspond in each case to one row of Table B

Table 112 : Compounds of formula I.H3 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is n-butyl, and the other variables for a compound correspond in each case to one row of Table B

Table 113 : Compounds of formula I.H3 ^* in which R ^AZ is CH2CºCH, R ⁶ is n-butyl, and the other variables for a compound correspond in each case to one row of Table B

Table 114 : Compounds of formula I.H3 ^* in which R ^AZ is C-C3H5, R ⁶ is n-butyl, and the other variables for a compound correspond in each case to one row of Table B

Table 115 : Compounds of formula I.H4 ^* in which R ^AZ is H, R ⁶ is n-butyl, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 116 : Compounds of formula I.H4 ^* in which R ^AZ is CH3, R ⁶ is n-butyl, and the other vari- ables for a compound correspond in each case to one row of T able B

Table 117 : Compounds of formula I.H4 ^* in which R ^AZ is C2H5, R ⁶ is n-butyl, and the other var- iables for a compound correspond in each case to one row of Table B

Table 118 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is n-butyl, and the other variables for a compound correspond in each case to one row of Table B

Table 119 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CºCH, R ⁶ is n-butyl, and the other variables for a compound correspond in each case to one row of Table B

Table 120 : Compounds of formula I.H4 ^* in which R ^AZ is C-C3H5, R ⁶ is n-butyl, and the other variables for a compound correspond in each case to one row of Table B

Table 121 : Compounds of formula I.H1 ^* in which R ^AZ is H, R ⁶ is CH2CF3, and the other varia- bles for a compound correspond in each case to one row of Table B Table 122 : Compounds of formula I.H1 ^* in which R ^AZ is CH3, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 123 : Compounds of formula I.H1 ^* in which R ^AZ is C2H5, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 124 : Compounds of formula I.H1 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 125 : Compounds of formula I.H1 ^* in which R ^AZ is CH2CºCH, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 126 : Compounds of formula I.H1 ^* in which R ^AZ is C-C3H5, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 127 : Compounds of formula I.H2 ^* in which R ^AZ is H, R ⁶ is CH2CF3, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 128 : Compounds of formula I.H2 ^* in which R ^AZ is CH3, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 129 : Compounds of formula I.H2 ^* in which R ^AZ is C2H5, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 130 : Compounds of formula I.H2 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 131 : Compounds of formula I.H2 ^* in which R ^AZ is CH2CºCH, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 132 : Compounds of formula I.H2 ^* in which R ^AZ is C-C3H5, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 133 : Compounds of formula I.H3 ^* in which R ^AZ is H, R ⁶ is CH2CF3, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 134 : Compounds of formula I.H3 ^* in which R ^AZ is CH3, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 135 : Compounds of formula I.H3 ^* in which R ^AZ is C2H5, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 136 : Compounds of formula I.H3 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 137 : Compounds of formula I.H3 ^* in which R ^AZ is CH2CºCH, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 138 : Compounds of formula I.H3 ^* in which R ^AZ is C-C3H5, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 139 : Compounds of formula I.H4 ^* in which R ^AZ is H, R ⁶ is CH2CF3, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 140 : Compounds of formula I.H4 ^* in which R ^AZ is CH3, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 141 : Compounds of formula I.H4 ^* in which R ^AZ is C2H5, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 142 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 143 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CºCH, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B Table 144 : Compounds of formula I.H4 ^* in which R ^AZ is C-C3H5, R ⁶ is CH2CF3, and the other variables for a compound correspond in each case to one row of Table B

Table 145 : Compounds of formula I.H1 ^* in which R ^AZ is H, R ⁶ is 1-[C(=S)NH ₂ ]-c-C ₃ H ₄ , and the other variables for a compound correspond in each case to one row of Table B

Table 146 : Compounds of formula I.H1 ^* in which R ^AZ is CH3, R ⁶ is 1-[C(=S)NH ₂ ]-c-C ₃ H ₄ , and the other variables for a compound correspond in each case to one row of Table B

Table 147 : Compounds of formula I.H1 ^* in which R ^AZ is C2H5, R ⁶ is 1-[C(=S)NH ₂ ]-c-C ₃ H ₄ , and the other variables for a compound correspond in each case to one row of Table B

Table 148 : Compounds of formula I.H1 ^* in which R ^AZ is CH ₂ CH=CH ₂ , R ⁶ is 1-[C(=S)NH ₂ ]-c- C3H4, and the other variables for a compound correspond in each case to one row of Table B Table 149 : Compounds of formula I.H1 ^* in which R ^AZ is CH2CºCH, R ⁶ is 1-[C(=S)NH ₂ ]-c- C3H4, and the other variables for a compound correspond in each case to one row of Table B Table 150 : Compounds of formula I.H1 ^* in which R ^AZ is C-C3H5, R ⁶ is 1-[C(=S)NH ₂ ]-c-C ₃ H ₄ , and the other variables for a compound correspond in each case to one row of Table B

Table 151 : Compounds of formula I.H2 ^* in which R ^AZ is H, R ⁶ is 1-[C(=S)NH ₂ ]-c-C ₃ H ₄ , and the other variables for a compound correspond in each case to one row of Table B

Table 152 : Compounds of formula I.H2 ^* in which R ^AZ is CH3, R ⁶ is 1-[C(=S)NH ₂ ]-c-C ₃ H ₄ , and the other variables for a compound correspond in each case to one row of Table B

Table 153 : Compounds of formula I.H2 ^* in which R ^AZ is C2H5, R ⁶ is 1-[C(=S)NH ₂ ]-c-C ₃ H ₄ , and the other variables for a compound correspond in each case to one row of Table B

Table 154 : Compounds of formula I.H2 ^* in which R ^AZ is CH ₂ CH=CH ₂ , R ⁶ is 1-[C(=S)NH ₂ ]-c- C3H4, and the other variables for a compound correspond in each case to one row of Table B Table 155 : Compounds of formula I.H2 ^* in which R ^AZ is CH2CºCH, R ⁶ is 1-[C(=S)NH ₂ ]-c- C3H4, and the other variables for a compound correspond in each case to one row of Table B Table 156 : Compounds of formula I.H2 ^* in which R ^AZ is C-C3H5, R ⁶ is 1-[C(=S)NH ₂ ]-c-C ₃ H ₄ , and the other variables for a compound correspond in each case to one row of Table B

Table 157 : Compounds of formula I.H3 ^* in which R ^AZ is H, R ⁶ is 1-[C(=S)NH ₂ ]-c-C ₃ H ₄ , and the other variables for a compound correspond in each case to one row of Table B

Table 158 : Compounds of formula I.H3 ^* in which R ^AZ is CH3, R ⁶ is 1-[C(=S)NH2]-c-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 159 : Compounds of formula I.H3 ^* in which R ^AZ is C2H5, R ⁶ is 1-[C(=S)NH2]-c-C3H4, and the other variables for a compound correspond in each case to one row of Table B

Table 160 : Compounds of formula I.H3 ^* in which R ^AZ is CH ₂ CH=CH ₂ , R ⁶ is 1-[C(=S)NH ₂ ]-c- C3H4, and the other variables for a compound correspond in each case to one row of T able B Table 161 : Compounds of formula I.H3 ^* in which R ^AZ is CH ₂ CºCH, R ⁶ is 1-[C(=S)NH ₂ ]-c- C3H4, and the other variables for a compound correspond in each case to one row of Table B Table 162 : Compounds of formula I.H3 ^* in which R ^AZ is C-C3H5, R ⁶ is 1-[C(=S)NH ₂ ]-c-C ₃ H ₄ , and the other variables for a compound correspond in each case to one row of Table B

Table 163 : Compounds of formula I.H4 ^* in which R ^AZ is H, R ⁶ is 1-[C(=S)NH ₂ ]-c-C ₃ H ₄ , and the other variables for a compound correspond in each case to one row of Table B

Table 164 : Compounds of formula I.H4 ^* in which R ^AZ is CH3, R ⁶ is 1-[C(=S)NH ₂ ]-c-C ₃ H ₄ , and the other variables for a compound correspond in each case to one row of Table B

Table 165 : Compounds of formula I.H4 ^* in which R ^AZ is C2H5, R ⁶ is 1-[C(=S)NH ₂ ]-c-C ₃ H ₄ , and the other variables for a compound correspond in each case to one row of Table B Table 166 : Compounds of formula I.H4 ^* in which R ^AZ is CH ₂ CH=CH ₂ , R ⁶ is 1-[C(=S)NH ₂ ]-c- C3H4, and the other variables for a compound correspond in each case to one row of Table B Table 167 : Compounds of formula I.H4 ^* in which R ^AZ is CH ₂ CºCH, R ⁶ is 1-[C(=S)NH ₂ ]-c- C3H4, and the other variables for a compound correspond in each case to one row of Table B Table 168 : Compounds of formula I.H4 ^* in which R ^AZ is C-C3H5, R ⁶ is 1-[C(=S)NH ₂ ]-c-C ₃ H ₄ , and the other variables for a compound correspond in each case to one row of Table B

Table 169 : Compounds of formula I.H1 ^* in which R ^AZ is H, R ⁶ is P-25, and the other variables for a compound correspond in each case to one row of Table B

Table 170 : Compounds of formula I.H1 ^* in which R ^AZ is CH3, R ⁶ is P-25, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 171 : Compounds of formula I.H1 ^* in which R ^AZ is C ₂ H ₅ , R ⁶ is P-25, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 172 : Compounds of formula I.H1 ^* in which R ^AZ is CH ₂ CH=CH ₂ , R ⁶ is P-25, and the other variables for a compound correspond in each case to one row of Table B

Table 173 : Compounds of formula I.H1 ^* in which R ^AZ is CH ₂ CºCH, R ⁶ is P-25, and the other variables for a compound correspond in each case to one row of Table B

Table 174 : Compounds of formula I.H1 ^* in which R ^AZ is C-C3H5, R ⁶ is P-25, and the other var- iables for a compound correspond in each case to one row of Table B

Table 175 : Compounds of formula I.H2 ^* in which R ^AZ is H, R ⁶ is P-25, and the other variables for a compound correspond in each case to one row of Table B

Table 176 : Compounds of formula I.H2 ^* in which R ^AZ is CH3, R ⁶ is P-25, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 177 : Compounds of formula I.H2 ^* in which R ^AZ is C ₂ H ₅ , R ⁶ is P-25, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 178 : Compounds of formula I.H2 ^* in which R ^AZ is CH ₂ CH=CH ₂ , R ⁶ is P-25, and the other variables for a compound correspond in each case to one row of Table B

Table 179 : Compounds of formula I.H2 ^* in which R ^AZ is CH ₂ CºCH, R ⁶ is P-25, and the other variables for a compound correspond in each case to one row of Table B

Table 180 : Compounds of formula I.H2 ^* in which R ^AZ is C-C3H5, R ⁶ is P-25, and the other var- iables for a compound correspond in each case to one row of Table B

Table 181 : Compounds of formula I.H3 ^* in which R ^AZ is H, R ⁶ is P-25, and the other variables for a compound correspond in each case to one row of Table B

Table 182 : Compounds of formula I.H3 ^* in which R ^AZ is CH3, R ⁶ is P-25, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 183 : Compounds of formula I.H3 ^* in which R ^AZ is C ₂ H ₅ , R ⁶ is P-25, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 184 : Compounds of formula I.H3 ^* in which R ^AZ is CH ₂ CH=CH ₂ , R ⁶ is P-25, and the other variables for a compound correspond in each case to one row of Table B

Table 185 : Compounds of formula I.H3 ^* in which R ^AZ is CH ₂ CºCH, R ⁶ is P-25, and the other variables for a compound correspond in each case to one row of Table B

Table 186 : Compounds of formula I.H3 ^* in which R ^AZ is C-C3H5, R ⁶ is P-25, and the other var- iables for a compound correspond in each case to one row of Table B

Table 187 : Compounds of formula I.H4 ^* in which R ^AZ is H, R ⁶ is P-25, and the other variables for a compound correspond in each case to one row of Table B Table 188 : Compounds of formula I.H4 ^* in which R ^AZ is CH3, R ⁶ is P-25, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 189 : Compounds of formula I.H4 ^* in which R ^AZ is C2H5, R ⁶ is P-25, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 190 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is P-25, and the other variables for a compound correspond in each case to one row of Table B

Table 191 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CºCH, R ⁶ is P-25, and the other variables for a compound correspond in each case to one row of Table B

Table 192 : Compounds of formula I.H4 ^* in which R ^AZ is C-C3H5, R ⁶ is P-25, and the other var- iables for a compound correspond in each case to one row of Table B

Table 193 : Compounds of formula I.H1 ^* in which R ^AZ is H, R ⁶ is P-28, and the other variables for a compound correspond in each case to one row of Table B

Table 194 : Compounds of formula I.H1 ^* in which R ^AZ is CH3, R ⁶ is P-28, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 195 : Compounds of formula I.H1 ^* in which R ^AZ is C2H5, R ⁶ is P-28, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 196 : Compounds of formula I.H1 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is P-28, and the other variables for a compound correspond in each case to one row of Table B

Table 197 : Compounds of formula I.H1 ^* in which R ^AZ is CH2CºCH, R ⁶ is P-28, and the other variables for a compound correspond in each case to one row of Table B

Table 198 : Compounds of formula I.H1 ^* in which R ^AZ is C-C3H5, R ⁶ is P-28, and the other var- iables for a compound correspond in each case to one row of Table B

Table 199 : Compounds of formula I.H2 ^* in which R ^AZ is H, R ⁶ is P-28, and the other variables for a compound correspond in each case to one row of Table B

Table 200 : Compounds of formula I.H2 ^* in which R ^AZ is CH3, R ⁶ is P-28, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 201 : Compounds of formula I.H2 ^* in which R ^AZ is C2H5, R ⁶ is P-28, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 202 : Compounds of formula I.H2 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is P-28, and the other variables for a compound correspond in each case to one row of Table B

Table 203 : Compounds of formula I.H2 ^* in which R ^AZ is CH2CºCH, R ⁶ is P-28, and the other variables for a compound correspond in each case to one row of Table B

Table 204 : Compounds of formula I.H2 ^* in which R ^AZ is C-C3H5, R ⁶ is P-28, and the other var- iables for a compound correspond in each case to one row of Table B

Table 205 : Compounds of formula I.H3 ^* in which R ^AZ is H, R ⁶ is P-28, and the other variables for a compound correspond in each case to one row of Table B

Table 206 : Compounds of formula I.H3 ^* in which R ^AZ is CH3, R ⁶ is P-28, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 207 : Compounds of formula I.H3 ^* in which R ^AZ is C2H5, R ⁶ is P-28, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 208 : Compounds of formula I.H3 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is P-28, and the other variables for a compound correspond in each case to one row of Table B

Table 209 : Compounds of formula I.H3 ^* in which R ^AZ is CH2CºCH, R ⁶ is P-28, and the other variables for a compound correspond in each case to one row of Table B Table 210 : Compounds of formula I.H3 ^* in which R ^AZ is C-C3H5, R ⁶ is P-28, and the other var- iables for a compound correspond in each case to one row of Table B

Table 21 1 : Compounds of formula I.H4 ^* in which R ^AZ is H, R ⁶ is P-28, and the other variables for a compound correspond in each case to one row of Table B

Table 212 : Compounds of formula I.H4 ^* in which R ^AZ is CH3, R ⁶ is P-28, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 213 : Compounds of formula I.H4 ^* in which R ^AZ is C2H5, R ⁶ is P-28, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 214 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is P-28, and the other variables for a compound correspond in each case to one row of Table B

Table 215 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CºCH, R ⁶ is P-28, and the other variables for a compound correspond in each case to one row of Table B

Table 216 : Compounds of formula I.H4 ^* in which R ^AZ is C-C3H5, R ⁶ is P-28, and the other var- iables for a compound correspond in each case to one row of Table B

Table 217 : Compounds of formula I.H1 ^* in which R ^AZ is H, R ⁶ is benzyl, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 218 : Compounds of formula I.H1 ^* in which R ^AZ is CH3, R ⁶ is benzyl, and the other vari- ables for a compound correspond in each case to one row of T able B

Table 219 : Compounds of formula I.H1 ^* in which R ^AZ is C2H5, R ⁶ is benzyl, and the other vari- ables for a compound correspond in each case to one row of Table B

Table 220 : Compounds of formula I.H1 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is benzyl, and the other variables for a compound correspond in each case to one row of Table B

Table 221 : Compounds of formula I.H1 ^* in which R ^AZ is CH2CºCH, R ⁶ is benzyl, and the other variables for a compound correspond in each case to one row of Table B

Table 222 : Compounds of formula I.H1 ^* in which R ^AZ is C-C3H5, R ⁶ is benzyl, and the other variables for a compound correspond in each case to one row of Table B

Table 223 : Compounds of formula I.H2 ^* in which R ^AZ is H, R ⁶ is benzyl, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 224 : Compounds of formula I.H2 ^* in which R ^AZ is CH3, R ⁶ is benzyl, and the other vari- ables for a compound correspond in each case to one row of Table B

Table 225 : Compounds of formula I.H2 ^* in which R ^AZ is C2H5, R ⁶ is benzyl, and the other vari- ables for a compound correspond in each case to one row of T able B

Table 226 : Compounds of formula I.H2 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is benzyl, and the other variables for a compound correspond in each case to one row of Table B

Table 227 : Compounds of formula I.H2 ^* in which R ^AZ is CH2CºCH, R ⁶ is benzyl, and the other variables for a compound correspond in each case to one row of Table B

Table 228 : Compounds of formula I.H2 ^* in which R ^AZ is C-C3H5, R ⁶ is benzyl, and the other variables for a compound correspond in each case to one row of Table B

Table 229 : Compounds of formula I.H3 ^* in which R ^AZ is H, R ⁶ is benzyl, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 230 : Compounds of formula I.H3 ^* in which R ^AZ is CH3, R ⁶ is benzyl, and the other vari- ables for a compound correspond in each case to one row of T able B

Table 231 : Compounds of formula I.H3 ^* in which R ^AZ is C2H5, R ⁶ is benzyl, and the other vari- ables for a compound correspond in each case to one row of T able B Table 232 : Compounds of formula I.H3 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is benzyl, and the other variables for a compound correspond in each case to one row of Table B

Table 233 : Compounds of formula I.H3 ^* in which R ^AZ is CH2CºCH, R ⁶ is benzyl, and the other variables for a compound correspond in each case to one row of Table B

Table 234 : Compounds of formula I.H3 ^* in which R ^AZ is C-C3H5, R ⁶ is benzyl, and the other variables for a compound correspond in each case to one row of Table B

Table 235 : Compounds of formula I.H4 ^* in which R ^AZ is H, R ⁶ is benzyl, and the other varia- bles for a compound correspond in each case to one row of Table B

Table 236 : Compounds of formula I.H4 ^* in which R ^AZ is CH3, R ⁶ is benzyl, and the other vari- ables for a compound correspond in each case to one row of T able B

Table 237 : Compounds of formula I.H4 ^* in which R ^AZ is C2H5, R ⁶ is benzyl, and the other vari- ables for a compound correspond in each case to one row of T able B

Table 238 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CH=CH2, R ⁶ is benzyl, and the other variables for a compound correspond in each case to one row of Table B

Table 239 : Compounds of formula I.H4 ^* in which R ^AZ is CH2CºCH, R ⁶ is benzyl, and the other variables for a compound correspond in each case to one row of Table B

Table 240 : Compounds of formula I.H4 ^* in which R ^AZ is C-C3H5, R ⁶ is benzyl, 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 invention with at least one mixing partner as defined herein. Preferred are binary mixtures of one compound of the invention as component I with one mixing partner as defined herein as component II. Pre- ferred weight ratios for such binary mixtures are from 5000:1 to 1 :5000, preferably from 1000:1 to 1 :1000, more preferably from 100:1 to 1 :100, particularly from 10:1 to 1 :10. In such binary mixtures, components I and II may be used in equal amounts, or an excess of component I, or an excess of component II may be used.

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

The following list M of pesticides, grouped and numbered according the Mode of Action Classi- fication of the Insecticide Resistance Action Committee (IRAC), together with which the corn- pounds of the invention can be used and with which potential synergistic effects might be pro- duced, is intended to illustrate the possible combinations, but not to impose any limitation:

M.1 Acetylcholine esterase (AChE) inhibitors: M.1A carbamates, e.g. aldicarb, alanycarb, ben- diocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethio- fencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triaz- amate; or M.1 B organophosphates, e.g. acephate, azamethiphos, azinphos-ethyl, azinphosme- thyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimetho- ate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl 0-(methoxyaminothio- phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, me- vinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profe- nofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirim- fos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, and vamidothion;

M.2. GABA-gated chloride channel antagonists: M.2A cyclodiene organochlohne compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), 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, kappa-bifenthrin, bioallethrin, bioallethrin S- cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta- cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, hep- tafluthrin, imiprothrin, meperfluthrin,metofluthrin, momfluorothrin, epsilon-momfluorothrin, per- methrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluth- rin, kappa-tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, and transfluthrin; or M.3B so- dium channel modulators such as DDT or methoxychlor;

M.4 Nicotinic acetylcholine receptor agonists (nAChR): M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M.4A.1 4,5-Dihydro-N-nitro-1-(2-oxiranylmethyl)-1 H-imidazol-2-amine, M.4A.2: (2E-)-1-[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentyliden ehydrazinecarboximidamide; or M4.A.3: 1 -[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 ,2,3,5,6,7-hexahydroim- idazo[1 ,2-a]pyridine; or M.4B nicotine; M.4C sulfoxaflor; M.4D flupyradifurone; M.4E triflume- zopyrim;

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

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

abamectin, emamectin benzoate, ivermectin, lepimectin, or milbemectin;

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

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

M.9 Chordotonal organ TRPV channel modulators, e.g. M.9B pymetrozine; pyrifluquinazon;

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 or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is- rae/ensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and 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, M.12C propargite, or M.12D tetra- difon; 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 bensultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;

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

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

M.17 Moulting disruptors, Dipteran, 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, e.g. amitraz;

M.20 Mitochondrial complex III electron transport inhibitors, e.g. M.20A hydramethylnon,

M.20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate;

M.21 Mitochondrial complex I electron transport inhibitors, e.g. M.21A METI acaricides and in- secticides 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, M.22B metaflumi- zone, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1 -[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoro- methoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methylphenyl)-2-[(4-chloro- phenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hyd razinecarboxamide;

M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid deriva- tives, e.g. spirodiclofen, spiromesifen, or spirotetramat; M.23.1 spiropidion;

M.24 Mitochondrial complex IV electron transport inhibitors, e.g. M.24A phosphine such as alu- minium 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, e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N 1 -{2-methyl-4-[1 ,2,2,2 -tetra- fluoro-1 -(trifluoromethyl)ethyl]phenyl}-N2-(1 -methyl-2-methylsulfonylethyl)phthalamid, M.28.2: (S)-3-Chloro-N 1 -{2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl}-N2-(1 -methyl-2 - methylsulfonylethyl)phthalamid, M.28.3: cyclaniliprole, or M.28.4: methyl-2-[3,5-dibromo-2-({[3- bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1 ,2-dimethylhydrazine- carboxylate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl ]-phenyl]- 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxa mide; M.28.5b) N-[4-chloro-2-[(di- ethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-( 3-chloro-2-pyridyl)-5-(trifluorome- thyl)pyrazole-3-carboxamide; M.28.5c) N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)car- bamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoro methyl)pyrazole-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)pyrazole-3-carboxamide; M.28.5h) N-[4,6-dibromo-2-[(diethyl- lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyri dyl)-5-(trifluoromethyl)pyrazole-3- carboxamide; M.28.5i) N-[2-(5-Amino-1 ,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1 - (3-chloro-2-pyridinyl)-1 H-pyrazole-5-carboxamide; M.28.5j) 3-Chloro-1 -(3-chloro-2-pyridinyl)-N- [2,4-dichloro-6-[[(1 -cyano-1 -methylethyl)amino]carbonyl]phenyl]-1 H-pyrazole-5-carboxamide; M.28.5k) 3-Bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5-di chloro-2-pyridyl)-1 H-py- razole-5-carboxamide; M.28.5I) N-[4-Chloro-2-[[(1 ,1-dimethylethyl)amino]carbonyl]-6-methyl- phenyl]-1 -(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide; or

M.28.6: cyhalodiamide; or

M.29: Chordotonal organ Modulators - undefined target site, e.g. flonicamid;

M.UN. insecticidal active compounds of unknown or uncertain mode of action, e.g. afidopyro- pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chino- methionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, fluralaner, metaldehyde, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, tioxazafen, M.UN.3: 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-aza- dispiro[4.2.4.2]-tetradec-1 1 -en-10-one,

M.UN.4: 3-(4’-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1- azaspiro[4.5]dec-3-en-2- one,

M.UN.5: 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]pheny l]-3-(trifluoromethyl)-1 H- 1 ,2,4-triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582);

M.UN.6: flupyrimin;

M.UN.8: fluazaindolizine; M.UN.9. a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol- 3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide; M.UN.9.b): fluxametamide; M.UN.10: 5-[3-[2,6- dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole;

M.UN.1 1.i) 4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.1 1.j) 4-cyano-3-[(4-cyano-2-me- thyl-benzoyl)amino]-N-[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2- fluoro-benzamide; M.UN.11.k) N-[5-[[2-chloro-6-cyano-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluorome- thyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-meth yl-benzamide; M.UN.1 1.1) N-[5- [[2-bromo-6-chloro-4-[2, 2, 2-trifluoro-1 -hydroxy-1 -(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cy- ano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.1 1.m) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3- hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cya no-phenyl]-4-cyano-2-methyl-ben- zamide; M.UN.1 1.n) 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoro- methyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.1 1.o) 4-cyano-N-[2-cyano- 5-[[2,6-dichloro-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl ]phenyl]-2-methyl- benzamide; M.UN.1 1.p) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,2-tetrafluoro-1-(trifluorome- thyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methy l-benzamide; or

M.UN.12. a) 2-(1 ,3-Dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; M.UN.12.b) 2-[6-[2-(5- Fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; M.UN.12. c) 2-[6-[2-(3-Pyridinyl)-5-thia- zolyl]-2-pyridinyl]-pyrimidine; M.UN.12.d) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2- carboxamide; M.UN.12.e) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-car boxamide;

M.UN.14a) 1-[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M.UN.14b) 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyrid in-5-ol ;

M.UN.16a) 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxa mide; or M.UN.16b) 1-(1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazol e-4-carboxamide; M.UN.16c)

N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl -ethyl)pyrazole-4-carboxamide;

M.UN.16d) 1-[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin -4-yl-pyrazole-4-carbox- amide; M.UN.16e) N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4- yl-pyrazole-4- carboxamide; M.UN.16f) 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4- car- boxamide; M.UN.16g) 1 -[1 -(1 -cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyraz ole-4- carboxamide; M.UN.16h) N-methyl-1 -(2-fluoro-1 -methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyra- zole-4-carboxamide; M.UN.16i) 1 -(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl- py- razole-4-carboxamide; or M.UN.16j) 1 -(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide,

M. UN.17a) N-(1 -methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M. UN.17b) N-cyclo- propyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M. UN.17c) N-cyclohexyl-2-(3-pyridinyl)-2H- indazole-4-carboxamide; M.UN.17d) 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-car- boxamide; M.UN.17e) 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole -5-carbox- amide; M.UN.17f) methyl 2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarbox ylate; M.UN.17g) N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indaz ole-5-carboxamide;

M.UN.17h) N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxa mide; M.UN.17i) 2-(3- pyridinyl )-N-(2-pyrimidinylmethyl )-2H-indazole-5-carboxamide; M.UN.17j) N-[(5-methyl-2-pyra- zinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide,

M.UN.18. tyclopyrazoflor;

M.UN.19 sarolaner, M.UN.20 lotilaner;

M.UN.21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1 -methyl-3-(1 ,1 ,2,2,2-pentaflu- oroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide; M. UN.22a 2-(3-ethylsulfonyl-2-pyridyl)- 3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M. UN.22b 2-[3-ethylsulfonyl-5-(trifluorome- thyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]p yridine;

M. UN.23a) 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3- yl]-N-[(4R)-2-ethyl-3- oxo-isoxazolidin-4-yl]-2-methyl-benzamide, or M. UN.23b) 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-is oxazolidin-4-yl]-2-methyl-benzamide;

M. UN.24a) N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1 ,1 ,2,2,2-pentafluoro- ethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide or M. UN.24b) N-[4-chloro-3-[(1 -cyanocyclopro- pyl)carbamoyl]phenyl]-2-methyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-car- boxamide; M.UN.25 acynonapyr; M.UN.26 benzpyrimoxan; M.UN.27 2-chloro-N-(1 -cyanocyclo- propyl)-5-[1 -[2-methyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazol-3-yl]pyr azol-4- yl]benzamide; M.UN.28 Oxazosulfyl;

M. UN.29a) [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydr opyran-2-yl] N-[4- [1 -[4-(trifluoromethoxy)phenyl]-1 ,2,4-triazol-3-yl]phenyl]carbamate; M. UN.29b)

[(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyr an-2-yl] N-[4-[1 -[4-(trifluorometh- oxy)phenyl]-1 ,2,4-triazol-3-yl]phenyl]carbamate; M. UN.29c) [(2S,3R,4R,5S,6S)-3,5-dimethoxy- 6-methyl-4-propoxy-tetrahydropyran-2-yl] N-[4-[1 -[4-(1 ,1 ,2,2,2-pentafluoroethoxy)phenyl]-1 ,2,4- triazol-3-yl]phenyl]carbamate; M.UN.29d) [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahy- dropyran-2-yl] N-[4-[1 -[4-(1 ,1 ,2,2,2-pentafluoroethoxy)phenyl]-1 ,2,4-triazol-3-yl]phenyl]carba- mate; M.UN.29.e) (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1 -[4-(trifluoromethoxy)phenyl]-1 ,2,4-tria- zol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one or M.UN.29f) (2Z)-3-(2-isopropylphenyl)- 2-[(E)-[4-[1 -[4-(1 ,1 ,2,2,2-pentafluoroethoxy)phenyl]-1 ,2,4-triazol-3-yl]phenyl]methylenehydra- zono]thiazolidin-4-one.

The commercially available compounds of the group M listed above may be found in The Pes- ticide Manual, 17th Edition, C. MacBean, British Crop Protection Council (2015) 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.

The M.4 cycloxaprid is known from WO2010/069266 and WO201 1/069456. M.4A.1 is known from CN 103814937; CN 105367557, CN 105481839. M.4A.2, guadipyr, is known from WO 2013/003977, and M.4A.3 (approved as paichongding in China) is known from WO

2007/101369. M.22B.1 is described in CN 10171577 and M.22B.2 in CN102126994. Spiropidion M.23.1 is known from WO 2014/191271. M.28.1 and M.28.2 are known from W02007/101540. M.28.3 is described in W02005/077934. M.28.4 is described in W02007/043677. M.28.5a) to M.28.5d) and M.28.5h) are described in WO 2007/006670, WO2013/024009 and WO

2013/024010, M.28.5i) is described in WO201 1/085575, M.28.5j) in W02008/134969, M.28.5k) in US201 1/046186 and M.28.5I) in WO2012/034403. M.28.6 can be found in WO2012/034472. M.UN.3 is known from W02006/089633 and M.UN.4 from W02008/06791 1. M.UN.5 is descri- bed in W02006/043635, and biological control agents on the basis of bacillus firmus are de- scribed in W02009/124707. Flupyrimin is described in WO2012/029672. M.UN.8 is known from WO2013/055584. M.UN.9.a) is described in WO2013/050317. M.UN.9.b) is described in WO 2014/126208. M.UN.10 is known from WO2010/060379. Broflanilide and M.UN.H .b) to

M.UN.1 1 .h) are described in WO2010/018714, and M.UN.1 1 i) to M.UN.1 1 .p) in WO

2010/127926. M.UN.12.a) to M.UN.12.C) are known from WO2010/006713, M.UN.12.d) and M.UN.12.e) are known from WO2012/000896. M. UN.14a) and M. UN.14b) are known from W02007/101369. M.UN.16.a) to M.UN.16h) are described in WO2010/034737, WO

2012/084670, and WO2012/143317, resp., and M.UN.16i) and M.UN.16j) are described in WO2015/055497. M. UN.17a) to M.UN.17.j) are described in WO2015/038503. M.UN.18 Tyclo- prazoflor is described in US2014/0213448. M.UN.19 is described in WO2014/036056. M.UN.20 is known from W02014/090918. M.UN.21 is known from EP2910126. M.UN.22a and M.UN.22b are known from WO2015/059039 and W02015/190316. M. UN.23a and M. UN.23b are known from WO2013/050302. M.UN.24a) and M.UN.24b) are known from WO2012/126766. Acynona- pyr M.UN.25 is known from WO 201 1/105506. Benzpyrimoxan M.UN.26 is known from WO 2016/104516. M.UN.27 is known from WO2016/174049. M.UN.28 Oxazosulfyl is known from WO2017/104592. M.UN.29a) to M.UN.29f) are known from W02009/102736 or

WO20131 16053.

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: azoxystrobin (A.1 .1 ), coumethoxystrobin (A.1 .2), coumoxystrobin (A.1.3), dimoxystrobin (A.1 .4), enestroburin (A.1 .5), fenaminstrobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1 .7), fluoxastrobin (A.1 .8), kresoxim-methyl (A.1.9), mande- strobin (A.1.10), metominostrobin (A.1 .1 1 ), orysastrobin (A.1 .12), picoxystrobin (A.1.13), pyra- clostrobin (A.1 .14), pyrametostrobin (A.1 .15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-/V- me- thyl-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-pyrazol-3-yl)oxylmethyl]phe- nyl]-/V-methoxy-carbamate (A.1 .22), 1 -[2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl- phenyl]-4-methyl-tetrazol-5-one (A.1.25), (Z;2£)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2- methoxyimino-/V,3-dimethyl-pent-3-enamide (A.1.34), (Z;2£)-5-[1-(4-chlorophenyl)pyrazol-3- yl]oxy-2-methoxyimino-/V,3-dimethyl-pent-3-enamide (A.1.35), pyriminostrobin (A.1.36), bifujun- zhi (A.1.37), 2-(ortho-((2,5-dimethylphenyl-oxymethylen)phenyl)-3-methoxy- acrylic acid meth- ylester (A.1.38);

inhibitors of complex III at Q, site: cyazofamid (A.2.1 ), amisulbrom (A.2.2),

[(6S,7/?,8/\ -8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino] -6-methyl-4,9-dioxo- 1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2.3), fenpicoxamid (A.2.4);

inhibitors of complex II: benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), bos- calid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyro- xad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyrazi- flumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21), inpyrfluxam (A.3.22), pyrapropoyne (A.3.23), fluindapyr (A.3.28), methyl (£)-2-[2-[(5-cyano-2-methyl-phe- noxy)methyl]phenyl]-3-methoxy-prop-2-enoate (A.3.30), isoflucypram (A.3.31), 2-(difluorome- thyl)-AA(1 ,1 ,3-trimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-/V-[(3/\ - 1 ,1 ,3-trimethylindan-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)-/V-(3-ethyl-1 ,1-di- methyl-indan-4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-/V-[(3/\ -3-ethyl-1 ,1-dime- thyl-indan-4-yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)-/V-(1 ,1-dimethyl-3-propyl-in- dan-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-/V-[(3/\ -1 ,1-dimethyl-3-propyl-in- dan-4-yl]pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)-/V-(3-isobutyl-1 ,1-dimethyl-indan-4- yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)-/V-[(3/\ -3-isobutyl-1 ,1-dimethyl-indan- 4-yl]pyridine-3-carboxamide (A.3.39);

other respiration inhibitors: diflumetorim (A.4.1 ); nitrophenyl derivates: binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7); organometal compounds: fentin salts, e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.11 ); silthiofam (A.4.12);

B) Sterol biosynthesis inhibitors (SBI fungicides)

C14 demethylase inhibitors: triazoles: azaconazole (B.1.1 ), bitertanol (B.1.2), bromucona- zole (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.1.11 ), 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), paclobutrazole (B.1.20), penconazole (B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1.30), 2-(2,4-difluorophenyl)-1 ,1-difluoro-3-(te- trazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridy l]propan-2-ol (B.1.31), 2-(2,4-difluoro- phenyl)-1 ,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phen yl]-2-pyridyl]propan-2-ol (B.1.32), ipfentrifluconazole (B.1.37), mefentrifluconazole (B.1.38), 2-(chloromethyl)-2-methyl-5- (p-tolylmethyl)-1-(1 ,2,4-triazol-1-ylmethyl)cyclopentanol (B.1.43); imidazoles: imazalil (B.1.44), pefurazoate (B.1.45), prochloraz (B.1.46), triflumizol (B.1.47); pyrimidines, pyridines, pipera- zines: fenarimol (B.1.49), pyrifenox (B.1.50), triforine (B.1.51 ), [3-(4-chloro-2-fluoro-phenyl)-5- (2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52);

Deltal 4-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 );

Other Sterol biosynthesis inhibitors: chlorphenomizole (B.4.1 );

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 (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);

other nucleic acid synthesis inhibitors: 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), 5-fluoro- 2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);

D) Inhibitors of cell division and cytoskeleton

tubulin inhibitors: benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D1.3), thiabenda- zole (D.1.4), thiophanate-methyl (D.1.5), 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyri- dazine (D.1.6), 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazi ne (D.1.7), /V-ethyl-2- [(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), /V-ethyl-2-[(3-ethynyl-8-methyl-6-quino- lyl)oxy]-2-methylsulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-/V-(2-fluoro- ethyl)butanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-/V-(2-fluoroethyl)-2- methoxy- acetamide (D.1.1 1), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-/V-propyl-butanamide (D.1.12), 2-[(3- ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-/V-propyl-acetami de (D.1.13), 2-[(3-ethynyl-8-me- thyl-6-quinolyl)oxy]-2-methylsulfanyl-/V-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6- quinolyl)oxy]-/V-(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phe- nyl)-/V-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-am ine (D.1.16);

other cell division inhibitors: diethofencarb (D.2.1), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7);

E) Inhibitors of amino acid and protein synthesis

methionine synthesis inhibitors: 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);

F) Signal transduction inhibitors

MAP / histidine kinase inhibitors: fluoroimid (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5);

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);

compounds affecting cell membrane permeability and fatty acides: propamocarb (G.4.1 ); inhibitors of oxysterol binding protein: 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 pyrazoM -yllacetylJpiperidin^- yl) 1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate (G.5.3), 4-[1 - [2-[3-(difluoromethyl)-5-methyl-pyrazol-1 -yl]acetyl]-4-piperidyl]-/V-tetralin-1 -yl-pyridine-2-carbox- amide (G.5.4), 4-[1 -[2-[3,5-bis(difluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-AAtetralin-1 -yl-pyri- dine-2-carboxamide (G.5.5), 4-[1 -[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1 -yl]acetyl]-4- piperidyl]-/V-tetralin-1 -yl-pyridine-2-carboxamide (G.5.6), 4-[1 -[2-[5-cyclopropyl-3-(difluorome- thyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-/V-tetralin-1 -yl-pyridine-2-carboxamide (G.5.7), 4-[1 -[2-[5- methyl-3-(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-/V-tetralin-1 -yl-pyridine-2-carboxamide (G.5.8), 4-[1 -[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-/V-tetralin-1 - yl-pyridine-2-carboxamide (G.5.9), 4-[1 -[2-[3,5-bis(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperi- dyl]-/V-tetralin-1 -yl-pyridine-2-carboxamide (G.5.10), (4-[1 -[2-[5-cyclopropyl-3-(trifluoromethyl)py- razol-1 -yl]acetyl]-4-piperidyl]-/V-tetralin-1 -yl-pyridine-2-carboxamide (G.5.1 1 );

H) Inhibitors with Multi Site Action

inorganic active substances: Bordeaux mixture (H.1.1 ), copper (H.1 .2), copper acetate (H.1 .3), copper hydroxide (H.1 .4), copper oxychloride (H.1.5), basic copper sulfate (H.1 .6), sul- fur (H.1.7);

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: 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 );

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 A/,5A ^L [1 ,4]di- thiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2A/,6AT)-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 (1.2.4), fenoxanil (1.2.5);

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), calcium phosphonate (J.1.1 1 ), potassium phosphonate (J.1 .12), potassium or sodium bicarbonate (J.1.9), 4-cyclopropyl-/V-(2,4-dimethoxyphenyl)thiadiazole-5-carboxam ide (J.1 .10);

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), diclocymet (K.1.7), diclomezine (K.1 .8), difenzoquat (K.1.9), difen- zoquat-methylsulfate (K.1 .10), diphenylamin (K.1 .1 1 ), fenitropan (K.1 .12), fenpyrazamine (K.1.13), flumetover (K.1 .14), flusulfamide (K.1 .15), flutianil (K.1 .16), harpin (K.1 .17), methasul- focarb (K.1.18), nitrapyrin (K.1 .19), nitrothal-isopropyl (K.1.20), tolprocarb (K.1.21 ), oxin-copper (K.1.22), proquinazid (K.1.23), tebufloquin (K.1 .24), tecloftalam (K.1 .25), triazoxide (K.1.26), N’- (4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl) -/V-ethyl-/V-methyl formamidine (K.1.27), /V ⁱ (4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-p henyl)-/V-ethyl-/V-methyl formamidine (K.1.28), /V ⁱ [4-[[3-[(4-chlorophenyl)methyl]-1 ,2,4-thiadiazol-5-yl]oxy]-2,5-dimethyl- phenyl]-/V-ethyl-/V-methyl-formamidine (K.1.29), /V^S-bromo-e-indan^-yloxy^-methyl-S-pyri- dyl)-/V-ethyl-/V-methyl-formamidine (K.1.30), /V ⁱ [5-bromo-6-[1 -(3,5-difluorophenyl)ethoxy]-2-me- thyl-3-pyridyl]-/V-ethyl-/V-methyl-formamidine (K.1.31 ), /V ⁱ [5-bromo-6-(4-isopropylcyclohexoxy)- 2-methyl-3-pyridyl]-/V-ethyl-/V-methyl-formamidine (K.1.32), /V^S-bromo^-methyl-e-il -phenyl- ethoxy)-3-pyridyl]-/V-ethyl-/V-methyl-formamidine (K.1.33), /V ⁱ (2-methyl-5-trifluoromethyl-4-(3- trimethylsilanyl-propoxy)-phenyl)-/V-ethyl-/V-methyl formamidine (K.1.34), /V^S-difluoromethyl-

2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-/V-ethyl- /V-methyl formamidine (K.1 .35), 2-(4- chloro-phenyl)-/V-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2 -prop-2-ynyloxy-acetamide (K.1.36),

3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-py ridine (pyrisoxazole) (K.1 .37), 3-[5-(4- methylphenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine (K.1 .38), 5-chloro-1 -(4,6-dimethoxy-pyrim- idin-2-yl)-2-methyl-1 TT-benzoimidazole (K.1 .39), ethyl (2)-3-amino-2-cyano-3-phenyl-prop-2-eno- ate (K.1 .40), picarbutrazox (K.1.41 ), pentyl /V-[6-[[(2)-[(1 -methyltetrazol-5-yl)-phenyl-methyle- ne]amino]oxymethyl]-2-pyridyl]carbamate (K.1 .42), but-3-ynyl /V-[6-[[(2)-[(1 -methyltetrazol-5-yl)- phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1 .43), 2-[2-[(7,8-difluoro-2-methyl-3- quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol (K.1.44), 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quino- lyl)oxy]phen-yl]propan-2-ol (K.1.45), quinofumelin (K.1 .47), 9-fluoro-2,2-dimethyl-5-(3-quinolyl)- 377-1 ,4-benzoxazepine (K.1 .49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1 .50), 2-[6-(3-fluoro-

4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline (K.1 .51 ), dichlobentiazox (K.1.52), N’-{ 2,5- dimethyl-4-phenoxy-phenyl)-/V-ethyl-/V-methyl-formamidine (K.1.53), pyrifenamine (K.1.54).

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 com- mercially available.

The active substances mentioned above, their preparation and their activity e. g. against harm- ful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by IUPAC nomenclature, their preparation and their pesti- cidal activity are 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 10/139271 , WO 1 1/028657, WO 12/168188, WO 07/006670, WO 1 1/77514;

WO 13/047749, WO 10/069882, WO 13/047441 , WO 03/16303, WO 09/90181 , WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/24010, WO 13/047441 ,

WO 13/162072, WO 13/092224, WO 1 1/135833, CN 1907024, CN 1456054, CN 103387541 ,

CN 1309897, WO 12/84812, CN 1907024, WO 09094442, WO 14/60177, WO 13/1 16251 ,

WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO 12/16551 1 , WO 1 1/081 174, WO 13/47441 ). Some compounds are identified by their CAS Registry Number which is separated by hyphens into three parts, the first consisting from two up to seven digits, the second consisting of two digits, and the third consisting of a single digit.

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, micro- bial 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 acti vators (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. E.g., biopesticides already play an important role in controlling downy mildew dis eases. 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 in- vention 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 ac- tivity: Ampelomyces quisqua/is, Aspergillus fiavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. megaterium, B. mojavensis, B. mycoides, B. pum/ius, B. simplex, B. so/isa/si, B. subtil is, B. subti/is var. amyloliquefaciens, Candida oleophila, C. saitoana, Ciavibac- ter michiganensis (bacteriophages), Coniothyrium minitans, Cryphonectria parasitica, Crypto coccus aibidus, Diiophosphora aiopecuri, Fusarium oxysporum, Cionostachys rosea f . catenu- iate (also named Giiociadium catenuiatum), Giiociadium roseum, Lysobacter antibioticus, L. en- zymogenes, Metschnikowia fructicoia, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor aibus, Paenibaciiius aivei, Paenibaciiius epiphyticus, P. poiymyxa, Pantoea vagans, Peniciiiium biiaiae, Ph/ebiopsis gig an tea, Pseudomonas s p . , Pseudomonas chi ora phis, Pseud o- zyma fioccuiosa, Pichia anomaia, Pythium oiigandrum, Sphaerodes mycoparasitica, Streptomy- ces griseoviridis, S. iydicus, S. vioiaceusniger, Taiaromyces fiavus, Trichoderma aspereiioides, T. aspereiium, T. atroviride, T. fertile, T. gamsii, T. harmatum, T. harzianum, T. polysporum, T. stromaticum, T. virens, T. viride, Typhu/a phacorrhiza, Ulocladium oudemansii, VerticiHium 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. israe/ensis, B. t. ssp. gaiieriae, B. t. ssp. kurstaki, B. t. ssp. tenebrionis, Beau- veria bassiana, B. brongniartii, Burkhoideria s p p . , Chromobacterium subtsugae, Cydia pomo- neiia granulovirus (CpGV), Cryptophiebia ieucotreta granulovirus (CrleGV), Fiavobacterium spp., Heiicoverpa armigera nucleopolyhedrovirus (HearNPV), Heiicoverpa zea nucleopolyhe- drovirus (HzNPV), Heiicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV), Heterorhab- ditis bacteriophora, isaria fumosorosea, Lecaniciiiium iongisporum, L. muscarium, Metarhizium anisopiiae, M. anisopiiae var. anisopiiae, M. anisopiiae var. acrid um, Nomuraea riieyi, Paeci- iomyces fumosoroseus, P. iiiacinus, Paenibaciiius popiiiiae, Pasteuria spp., P. nishizawae, P. penetrans, P. ramosa, P. thornea, P. usgae, Pseudomonas f/uorescens, Spodoptera iittoraiis nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, S. feitiae, S. kraussei, Streptomy- ces gaibus, S. microfiavusr,

L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal, pheromone and/or nemat- icidal activity: L-carvone, citral, (F^- ^-dodecadien-l-yl acetate, ethyl formate, (E,Z-2, 4-ethyl decadienoate (pear ester), (Z,Z,E)-7A 1 ,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavanulyl senecioate, cis-jasmone, 2-methyl 1-butanol, methyl eugenol, methyl jasmonate, (F,2)-2,13-octadecadien-1-ol, (F,2)-2,13-octadecadien-1-ol acetate, ( 2)-3,13-octadecadien-1- ol, (/ )-1-octen-3-ol, pentatermanone, {E,Z,Z)- 3,8,11-tetradecatrienyl acetate, ( ;£)-9,12-tetra- decadien-1-yl acetate, (2)-7-tetradecen-2-one, (2)-9-tetradecen-1-yl acetate, (2)-1 1 -tetrad ece- nal, (2)-11-tetradecen-1-ol, extract of Chenopodium ambrosiodes, Neem oil, Quillay extract;

L5) Microbial pesticides with plant stress reducing, plant growth regulator, plant growth pro- moting and/or yield enhancing activity: Azospirillum amazonense, A. brasi/ense, A. iipoferum, A. irakense, A. haiopraeferens, Bradyrhizobium spp. , B. eikanii, B. japonicum, B. iiaoningense, B. iupini, Deiftia acidovorans, G/omus intraradices, Mesorhizobium spp., Rhizobium ieguminosa- rum bv. phased i, R. /. bv. trifoiii, R. /. bv. viciae, R. tropici, Sinorhizobium meiiioti

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 pro- moting 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 lit- erature, registered and/or are commercially available: mixtures of Aureobasidium puiiuians DSM 14940 and DSM 14941 isolated in 1989 in Konstanz, Germany (e. g. blastospores in Blos- som Protect® from bio-ferm GmbH, Austria), Azospirillum brasiiense S 245 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. amyloliquefa ciens spp. plantarum Dl l isolated from air in Kikugawa-shi, Japan (US 20130236522 A1 ; FERM BP-8234; e. g. Double Nickel™ 55 WDG from Certis LLC, USA), B. amyloliquefaciens spp. plantarum PZ 24 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, Germany), B. amyloliquefaciens ssp. plantarum MBI600 isolated from faba bean in Sutton Bon- ington, Nottinghamshire, U.K. at least before 1988 (also called 1430; NRRL B-50595;

US 2012/0149571 A1 ; e. g. Integral® from BASF Corp., USA), B. amyloliquefaciens spp. planta- /I//77 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. plantarum TJ1000 isolated in 1992 in South Dakoda, U.S.A. (also called 1 BE; ATCC BAA-390; CA

2471555 A1 ; e. g. QuickRoots™ from TJ Technologies, Watertown, SD, USA), B. firmus CNCM 1-1582, a variant of parental strain EIP-N1 (CNCM 1-1556) isolated from soil of central plain area of Israel (WO 2009/126473, US 6,406,690; e. g. Votivo® from Bayer CropScience LP, USA), B. pumi/us GHA 180 isolated from apple tree rhizosphere in Mexico (IDAC 260707-01 ; e. g. PRO- MIX® BX from Premier Horticulture, Quebec, Canada), B. pumi/us INR-7 otherwise referred to as BU-F22 and BU-F33 isolated at least before 1993 from cucumber infested by Erwinia tra- cheiphHa (NRRL B-50185, NRRL B-50153; US 8,445,255), B. pumHus YEP F 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. pu- mi/us 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. subti/is FB17 also called UD 1022 or UD10-22 isolated from red beet roots in North America (ATCC PTA-1 1857; System. Appl. Mi- crobiol. 27, 372-379, 2004; US 2010/0260735; WO 201 1/109395); B. thuringiensis ssp. aizawai ABTS-1857 isolated from soil taken from a lawn in Ephraim, Wisconsin, U.S.A., in 1987 (also called ABG-6346; ATCC SD-1372; e. g. XenTari® from BioFa AG, Munsingen, Germany), B. t. ssp. kurstaki ABTS-351 identical to HD-1 isolated in 1967 from diseased Pink Bollworm black larvae in Brownsville, Texas, U.S.A. (ATCC SD-1275; e. g. Dipel® DF from Valent BioSciences, IL, USA), B. t. ssp. kurstakiS A isolated from E. saccharina larval cadavers (NRRL B-50753; e. g. Beta Pro® from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. t. ssp. tenebrionis NB-176-1 , a mutant of strain NB-125, a wild type strain isolated in 1982 from a dead pupa of the beetle Tenebrio molitor (DSM 5480; EP 585 215 B1 ; e. g. Novodor® from Valent BioSciences, Switzerland), Beauveria bassiana GV\A (ATCC 74250; e. g. BotaniGard® 22WGP from Laver- lam Int. Corp., USA), B. bassiana SNA (ATCC 74040; e. g. Naturalis® from CBC (Europe)

S.r.L, Italy), B. bassiana PPRI 5339 isolated from the larva of the tortoise beetle Conchyloctenia punctata (NRRL 50757; e. g. Broad Band® from BASF Agricultural Specialities (Pty) Ltd., South Africa), Bradyrhizobium e!kanii 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 previ- ously 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 52 _> 2c 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-Wd variant of strain USDA 138 (INTA E109, SEMIA 5085; Eur. J. Soil Biol. 45, 28-35, 2009; Biol. Fertil. Soils 47, 81-89, 2011 ); B.ja- ponicum 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 com- mercial 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, Ja- pan, in 2008 (NRRL B-50319; WO 2013/032693; Marrone Bio Innovations, Inc., USA), Coni- othyrium minitans CON/M/91-08 isolated from oilseed rape (WO 1996/021358; DSM 9660; e. g. Contans® WG, Intercept® WG from Bayer CropScience AG, Germany), harpin (alpha-beta) protein (Science 257, 85-88, 1992; e. g. Messenger™ or HARP-N-Tek from Plant Health Care pic, U.K.), Helicoverpa armigera nudeo oty edrovnus (HearNPV) (J. Invertebrate Pathol. 107, 112-126, 2011 ; e. g. Helicovex® from Adermatt Biocontrol, Switzerland; Diplomata® from Kop- pert, Brazil; Vivus® Max from AgBiTech Pty Ltd., Queensland, Australia), Helicoverpa zea sin- gle capsid nucleopolyhedrovirus (HzSNPV) (e. g. Gemstar® from Certis LLC, USA), Heii- coL/e/pa ea nucleopolyhedrovirus ABA-NPV-U (e. g. Heligen® from AgBiTech Pty Ltd., Queensland, Australia), Heterorhabditis bacteriophora (e. g. Nemasys® G from BASF Agricul- tural Specialities Limited, UK), Isaria fumosorosea Apopka-97 isolated from mealy bug on gynura in Apopka, Florida, U.S.A. (ATCC 20874; Biocontrol Science Technol. 22(7), 747-761 , 2012; e. g. PFR-97™ or PreFeRal® from Certis LLC, USA), Metarhizium anisopliae var. an- isopHae 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. for- merly Shemer® from Agrogreen, Israel), PaecHomyces Hacinus2o' '\ isolated from infected nem- atode eggs in the Philippines (AGAL 89/030550; W01991/02051 ; Crop Protection 27, 352-361 , 2008; e. g. BioAct®from Bayer CropScience AG, Germany and MeloCon® from Certis, USA), PaenibaciHus 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 Speciali- ties (Pty) Ltd., South Africa), PaenibaciHus strains isolated from soil samples from a variety of European locations including Germany: P. epiphyticus Lu17015 (WO 2016/020371 ; DSM 26971 ), P. po/ymyxa ssp. piantarum Lu^ Qll 4 (WO 2016/020371 ; DSM 26969), P. p. ssp.

piantarums dim Lu17007 (WO 2016/020371 ; DSM 26970); Pasteuria nishizawae Pn1 isolated from a soybean field in the mid-2000s in Illinois, U.S.A. (ATCC SD-5833; Federal Register 76(22), 5808, February 2, 2011 ; e.g. Clariva™ PN from Syngenta Crop Protection, LLC, USA), Peniciiiium biiaiae (also called P. biiaii) 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, Can- ada), Reynoutria sachalinensis extract (EP 0307510 B1 ; e. g. Regalia® SC from Marrone Bioln- novations, Davis, CA, USA or Milsana® from BioFa AG, Germany), Steinernema carpocapsae (e. g. Millenium® from BASF Agricultural Specialities Limited, UK), S. feitiae {e. g. Nemashield® from BioWorks, Inc., USA; Nemasys® from BASF Agricultural Specialities Limited, UK), Strepto- myces microfiavus NRRL B-50550 (WO 2014/124369; Bayer CropScience, Germany), Tricho- derma 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 Biological Marketing Inc., Van Wert, OH,

USA).

According to the invention, the solid material (dry matter) of the biopesticides (with the excep- tion 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 feitiae.

When mixtures comprising microbial pesticides are employed in crop protection, the applica- tion rates preferably range from about 1 x 10 ⁶ to 5 x 10 ¹⁵ (or more) CFU/ha, preferably from about 1 x 10 ⁸ to about 1 x 10 ¹³ CFU/ha, and even more preferably from about 1 x 10 ⁹ to about 1 x 10 ¹² CFU/ha. In the case of (entomopathogenic) nematodes as microbial pesticides (e. g. Stei nernema feitiae), the application rates preferably range inform about 1 x 10 ⁵ to 1 x 10 ¹² (or more), more preferably from 1 x 10 ⁸ to 1 x 10 ¹¹ , even more preferably from 5 x 10 ⁸ to 1 x 10 ¹⁰ 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 applica- tion rates with respect to plant propagation material preferably range from about 1 x 10 ⁶ to 1 x 10 ¹² (or more) CFU/seed. Preferably, the concentration is about 1 x 10 ⁶ to about 1 x 10 ⁹ 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 10 ⁷ to 1 x 10 ¹⁴ (or more) CFU per 100 kg of seed, preferably from 1 x 10 ⁹ to about 1 x 10 ¹² 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 custom- ary 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 propagation 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 Mono- graph 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, surfac- tants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec- tive colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimu- lants, 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 frac- tions 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, al- kylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, lime- stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. ammo- nium 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 col- loid, 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, sul-fa- tes, 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, sulfona- tes of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sul- fates 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. Exam- pies of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Ex- amples 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 corn- pounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable am- photeric surfactants are alkylbetains and imidazolines. Suitable block polymers are block poly- mers 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. Suita- ble 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 in- vention 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), anor- ganic 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 polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

Examples for composition types and their preparation are:

i) Water-soluble concentrates (SL, LS)

10-60 wt% of a compound I according to the invention and 5-15 wt% wetting agent (e.g. alco- hol 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. polyvi- nylpyrrolidone) 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-insol- uble 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 wa- ter 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 alco- hol 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 sub- stance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.

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

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 solu- tion 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 dis persion 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 sub- stance. 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 compris- ing 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’-di- isocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alco- hol). 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 corn- position.

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% col- ora nts.

The agrochemical compositions generally comprise between 0.01 and 95%, preferably be- tween 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active 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 comprising them as premix or, if appropriate not until immedi- ately 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 agrochem- ical composition is made up with water, buffer, and/or further auxiliaries to the desired applica- tion 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 in- vention 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 pre- sent 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 in- vention 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 pro- tection 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 infesta- tion by animal pests, with a pesticidally effective amount of a compound of the present inven- tion.

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 control- ling 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. Fur- thermore, 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 compris- ing said mixtures as defined above. The components of said mixture can be applied simultane- ously, 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 pellet ing. In furrow applications typically include the steps of making a furrow in cultivated land, seed- ing 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 com- pounds/compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus, i.e. habi- tat, 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 in- sect 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, nec- tarines, 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 mel- ons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grape- fruits or mandarins; vegetables, such as eggplant, spinach, lettuce (e.g. iceberg lettuce), chic- ory, 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, to- bacco, 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 "cultivated plants" is to be understood as including plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.

Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemi- cals, but also techniques of targeted mutagenesis, in order to create mutations at a specific lo- cus of a plant genome. Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the tar- geting effect.

Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination. Typically, one or more genes are integrated into the ge- nome of a plant in order to add a trait or improve a trait. These integrated genes are also re- ferred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants. The process of plant transformation usually produces several transformation events, wich differ in the genomic locus in which a transgene has been integrated. Plants corn- prising a specific transgene on a specific genomic locus are usually described as comprising a specific“event”, which is referred to by a specific event name. Traits which have been intro- duced in plants or hae been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.

Herbicide tolerance has been created by using mutagenesis as well as using genetic engineer- ing. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbi- cides by conventional methods of mutagenesis and breeding comprise plant varieties commer- cially available under the name Clearfield ^® . However, most of the herbicide tolerance traits have been created via the use of transgenes.

Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbi- cides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and 4-hy- droxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.

Transgenes wich have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601 , gat4621 and goxv247, for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, for tolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csr1-2, for tolerance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.

Transgenic corn events comprising herbicide tolerance genes are e.g., but not excluding oth- ers, DAS40278, MON801 , MON802, MON809, MON810, MON832, MON87411 , MON87419, MON87427, MON88017, MON89034, NK603, GA21 , MZHG0JG, HCEM485, VCO-01981-5, 676, 678, 680, 33121 , 4114, 59122, 98140, Bt10, Bt176, CBH-351 , DBT418, DLL25, MS3,

MS6, MZIR098, T25, TC1507 and TC6275.

Transgenic soybean events comprising herbicide tolerance genes are e.g., but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.

Transgenic cotton events comprising herbicide tolerance genes are e.g., but not excluding oth- ers, 19-51 a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN1021 1 , BXN10215,

BXN 10222, BXN 10224, MON1445, MON1698, MON88701 , MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.

Transgenic canola events comprising herbicide tolerance genes are e.g., but not excluding others, MON88302, HCR-1 , HCN10, HCN28, HCN92, MS1 , MS8, PHY14, PHY23, PHY35, PHY36, RF1 , RF2 and RF3.

Insect resistance has mainly been created by transferring bacterial genes for insecticidal pro- teins to plants. Transgenes which have most frequently been used are toxin genes of Bacillus spec and synthetic variants thereof, like cry1A, crylAb, cry1Ab-Ac, crylAc, cry1A.105, cry1 F, cry1 Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1 , cry34Ab1 , cry35Ab1 , cry9C, vip3A(a), vip3Aa20. However, also genes of plant origin have been transferred to other plants. In particu- lar genes coding for protease inhibitors, like CpTI and pinll. A further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate insect genes. An example for such a transgene is dvsnf7.

Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA are e.g., but not excluding others, Bt10, Bt1 1 , Bt176, MON801 , MON802, MON809, MON810, MON863, MON87411 , MON88017, MON89034, 33121 , 41 14, 5307, 59122, TC1507, TC6275, CBH-351 , MIR162, DBT418, and MZIR098.

Transgenic soybean events comprising genes for insecticidal proteins are e.g., but not exclud- ing others, MON87701 , MON87751 , and DAS-81419.

Transgenic cotton events comprising genes for insecticidal proteins are e.g., but not excluding others, SGK321 , MON531 , MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BN LA-601 , Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB1 19, and SGK321.

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

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

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

Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combination of traits are herbicide toler- ance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbi- cide tolerance and tolerance to abiotic conditions.

Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art. E.g., detailed information 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/gmap- provaldatabase) and the“Center for Environmental Risk Assessment (CERA)” (http://cera- gmc.org/GMCropDatabase), Further information on specific events and methods to detect them can be found for canola events MS1 , MS8, RF3, GT73, MON88302, KK179 in W001/031042, WO01/041558, W001/041558, W002/036831 , W01 1/153186, W013/003558, for cotton events MON1445, MON15985, MON531 (MON15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210-23, COT67B, GHB614, T304-40, GHB1 19, MON88701 , 81910 in WO02/034946, W002/100163, W002/100163, W003/013224, WO04/072235, WO04/039986, WO05/103266, WO05/103266, WO06/128573, W007/017186, W008/122406, W008/151780, WO12/134808, W013/112527, for corn events GA21 , MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307,

4114, MON87427, DAS40278, MON8741 1 , 33121 , MON87403, MON87419 in W098/044140, US02/102582, US03/126634, WO04/099447, WO04/011601 , WO05/103301 , W005/061720, W005/059103, WO06/098952, WO06/039376, US2007/292854, WO07/142840,

WO07/140256, W008/112019, W009/103049, WO09/1 11263, W010/077816, W011/084621 , W01 1/062904, W01 1/022469, W013/169923, W014/1 16854, W015/053998, W015/142571 , for potato events E12, F10, J3, J55, V1 1 , X17, Y9 in W014/178910, W014/178913,

W014/178941 , W014/179276, W016/183445, W017/062831 , W017/062825, for rice events LLRICE06, LLRICE601 , LLRICE62 in WO00/026345, WO00/026356, WO00/026345 for soy- bean events H7-1 , MON89788, A2704-12, A5547-127, DP305423, DP356043, MON87701 , MON87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2,

DAS81419, DAS81419 x DAS44406-6, MON87751 in WO04/074492, W006/130436,

WO06/108674, WO06/108675, WO08/054747, W008/002872, WO09/064652, WO09/102873, W010/080829, W010/037016, W011/066384, W011/034704, WO12/051199, WO12/082548, W013/016527, WO13/016516, W014/201235.

The use of compositions according to the invention on cultivated plants may result in effects which are specific to a cultivated plant comprising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors.

Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.

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, rhi- zomes, 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 ac- cording to the prevailing conditions such as desired pesticidal effect and duration, weather, tar- get 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 in- gredients 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 invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling’s roots and shoots against soil pests and foliar insects. The invention there- fore also relates to a method for the protection of seeds from insects, in particular from soil in- sects, and of the seedling's roots and shoots from insects, in particular from soil and foliar in- sects, said method comprising treating the seeds before sowing and/or after pregermination with a compound of the invention. The protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling’s shoots from piercing and sucking insects, chewing insects and nematodes.

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 car- ried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.

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

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 treat- ment 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. Prefera- bly, the formulations are applied such that germination is not included.

The active substance concentrations in ready-to-use formulations, which may be obtained af- ter 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 formu- lation 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 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 invention, or an ag- riculturally useful salt thereof, as defined herein. The amount of the compound of the 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 invention may also be used for improving the health of a plant. There- fore, the invention also relates to a method for improving plant health by treating a plant, plant propagation material and/or the locus where the plant is growing or is to grow with an effective and non-phytotoxic amount of a compound of the invention.

As used herein“an effective and non-phytotoxic amount” means that the compound is used in 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 (e.g., 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 meth- ods 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 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 cock- roaches.

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, e.g., 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 polyorganosaccha- rides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even mo- lasses 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 in- sect 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 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 sta- bilizers, 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 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 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 prefer- ably comprise a mixture including the insecticide, optionally a repellent and at least one binder.

The compounds of the invention and its compositions can be used for protecting wooden ma- terials 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 hu- man being (e.g. when the pests invade into houses and public facilities).

Customary application rates in the protection of materials are, e.g. from 0.001 g to 2000 g or from 0.01 g to 1000 g of active compound per 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 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, Aderis 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. exdamationis, A. fucosa, A. ipsilon, A. orthogoma, A. segetum, A. subterranea; Alabama argillacea, Aleurodicus dispersus, Alsophila pometaria, Ampelophaga rubiginosa, Amyelois transitella, Anacampsis sardtella, Ana- gasta kuehniella, Anarsia lineatella, Anisota senatoria, Antheraea pernyi, Anticarsia

(=Thermesia) 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 viridi- grisea, Autographa gamma, Autographa nigrisigna, Barathra brassicae, Bedel Ha spp., Bonagota salubricola, Borbo dnnara, Bucculatrix thurberiella, Bupalus piniarius, Busseo/a spp., Cacoeda spp. such as C. murinana, C. podana; Cadoblastis cadorum, Cadra cautella, Ca/ingo brazilien- sis, Caloptilis theivora, Capua reticulana, Carposina spp. such as C. niponensis, C. sasakii; Ce- phus s ., Chaetocnema aridula, Cheimatobia brumata, ChHo spp. such as C. Indicus, C. sup- pressa/is, C. partellus; Choreutis pariana, Choristoneura spp. such as C. confHdana, C. fumife- rana, C. longicellana, C. murinana, C. ocddentalis, C. rosaceana; Chrysodeixis (=Pseudop/u- sia) spp. such as C. eriosoma, C. indudens; Cirphis unipunda, Ctysia ambiguella, Cnapha/oce- rus spp. , Cnapha/ocrocis medinaHs, Cnephasia spp., Cochylis hospes, Co/eophora s ., Co/ias eurytheme, Conopomorpha spp., Conotrache!us spp. , Copitarsia spp., Corcyra cepha/onica, Crambus caliginosellus, Crambus teterrellus, Crocidosema (=Epinotia) aporema, CydaHma (=Diaphania) perspectah ^' s, Cydia (=Carpocapsa) spp. such as C. pomonella, C. latiferreana; Da- laca noctuides, Datana integerrima, Dasychira pinico/a, Dendrolimus spp. such as D. pini, D. spectab/i/s, D. sibiricus; Desmia funeratis, Diaphania spp. such as D. nitidatis, D. hyaHnata; Di- atraea grandiosella, Diatraea saccharaHs, Diphthera festiva, Earias spp. such as E. insutana, E. vittella; Ecdytotopha aurantianu, Egira (=Xylomyges) curiatis, Elasmopalpus iignose/ius, Eldana saccharina, Endopiza viteana, Ennomos subsignaria, Eoreuma loftini, Ephestia spp. such as E. cautella, E. elutella, E. kuehniella; Epinotia aporema, Epiphyas postvittana, Erannis tiHaria, Erio- nota thrax, Etiella spp., Eulia spp., EupoecHia ambiguella, Euprodis chrysorrhoea, Euxoa spp., Evetria bouliana, Faronta albilinea, Feltia spp. such as F. subterranean; Galleria mellonella, GraciHaria spp., Grapholita spp. such as G. funebrana, G. mo/esta, G. inopinata; Ha/ysidota spp., Harrisina americana, Hedy/epta s ., Heh ^' coverpa spp. such as H. armigera (=Heliothis armigera), H. zea (=Heliothis zea); He/iothis spp. such as H. assu!ta, H. subf!exa, H. virescens; Hellula spp. such as H. undalis, H. rogatalis; Helocoverpa gelotopoeon, Hemiieuca oliviae, Her- petogramma licarsisalis, Hibernia defoiiaria, Hofmannophiia pseudospreteiia, Homoeosoma eiecteiium, Homona magnanima, Hypena scabra, Hyphantria cunea, Hyponomeuta padeiia, Hyponomeuta malinellus, Kakivoria fiavofasciata, Keiferia iycopersiceiia, Lambdina fisceiiaria fisceiiaria, Lambdina fisceiiaria iugubrosa, Lamprosema indicate, Laspeyresia moiesta, Legumi- nivora giycinivoreiia, Lerodea eufaia, Leucinodes orbonaiis, Leucoma saiicis, Leucoptera spp. such as L. coffeeiia, L. sciteiia; Leuminivora iycinivoreiia, Lithocoiietis biancardeiia, Lithophane antennata, Liattia octo (=Amyna axis), Lobesia botrana, L ophocampa spp., Loxagrotis aibicosta, Loxostege spp. such as L. sticticaiis, L. cereraiis; Lymantria spp. such as L. dispar, L. monacha; Lyonetia cierkeiia, Lyonetia prunifoiieiia, Maiacosoma spp. such as M. americanum, M. caiiforni- cum, M. constrictum, M. neu stria; Mamestra spp. such as M. brassicae, M. configurata; Mam- stra brassicae, Manduca spp. such as M. quinquemacuiata, M. sexta; Marasmia spp, Marmara spp., Maruca testu/a/is, Megaiopyge ianata, Meianchra picta, Meianitis ieda, Mods spp. such as M. iapites, M. repanda; Mods iatipes, Monochroa fragariae, Mythimna separata, Nemapogon doaceiia, Neoieucinodes eiegantaiis, Nepytia spp., Nymphu/a spp., Oiketicus spp., Omiodes in- dicata, Omphisa anastomosaiis, Operophtera brumata, Orgyia pseudotsugata, Oria spp., Ortha- ga thyrisaiis, Ostrinia spp. such as O. nubiiaiis; Ouiema oryzae, Paieacrita vernata, Panoiis fiammea, Parnara spp., Papaipema nebris, Papiiio cresphontes, Paramyeiois transiteiia, Paran- threne regaiis, Paysandisia archon, Pectinophora spp. such as P. gossypieiia; Peridroma sau- cia, Periieucoptera spp., such as P. coffeeiia; Phaiera bucephaia, Phryganidia caiifornica, Phthorimaea spp. such as P. opercuieiia; Phyiiocnistis citreiia, Phyiionorycter spp. such as P. biancardeiia, P. crataegeiia, P. issikii, P. ringonieiia; Pier is spp. such as P. brassicae, P. rapae, P. napi; PHocrocis tripunctata, Piathypena scabra, Piatynota spp. such as P. fiavedana, P. idae- usa/is, P. stuitana; Piatyptiiia carduidactyia, Piebejus argus, Piodia interpuncteiia, Piusia spp, Piuteiia macuiipennis, Piuteiia xyiosteiia, Pontia protodica, Prays spp., Prodeni a spp., Proxenus iepigone, Pseudaietia spp. such as P. sequax, P. unipuncta; Pyrausta nubiiaiis, Rachipiusia nu, Richia aibicosta, Rhizobius ventraiis, Rhyacionia frustrana, Sabuiodes aegrotata, Schizura con- cinna, Schoenobius spp. , Schreckensteinia festaiieiia, Scirpophaga spp. such as S. incertuias,

S. innotata; Scotia segetum, Sesamia spp. such as S. inferens, Seudyra subfiava, Sitotroga ce- reaieiia, Sparganothis piHeriana, Spiionota iechriaspis, S. oceiiana, Spodoptera (=Lamphygma) spp. such as S. cosmoides, S. eridania, S. exigua, S. frugiperda, S. iatisfascia, S. iittoraiis, S. iitura, S. omithogaiii; Stigmeiia spp., Stomopteryx subsecive/ia, Strymon bazochii, Syiepta dero- gata, Synanthedon spp. such as S. exitiosa, Tecia so/anivora, Teiehin iicus, Thaumatopoea pityocampa, Thaumatotibia (=Cryptophiebia) ieucotreta, Thaumetopoea pityocampa, Theda spp., Theresimima ampeiophaga, Thyrinteina spp, Tiidenia inconspicueiia, Tinea spp. such as

T. doaceiia, T pellionella; Tineoia bissei/ie/ia, Tortrix spp. such as T. viridana; Trichophaga ta- petzeiia, Trichopiusia spp. such as T. ni; Tuta (=Scrobipaipuia) absoiuta, Udea spp. such as U. rubigaiis, U. rubigaiis; Virachoia spp., Yponomeuta padeiia, and Zeiraphera canadensis;

insects from the order of Coleoptera, e.g. Acaiymma vittatum, Acanthoscehdes obtectus, Adore tus spp., Ageiastica aini, Agri/us spp. such as A. anxius, A. pianipennis, A. sinuatus; Agri- otes spp. such as A. fuscicoiiis, A. iineatus, A. obscurus; A/phitobius diaperinus, Amphimaiius so/stitia/is, Anisandrus dispar, Anisopiia austriaca, Anobium punctatum, Anomaia corpuienta, Anomaia rufocuprea, Anopiophora spp. such as A. giabripennis; Anthonomus spp. such as A. eugenii, A. grandis, A. pomorum; Anthrenus spp. , Aphthona euphoridae, Apion spp., Apogonia spp., Athous haemorrhoidaiis, A to maria spp. such as A. linearis; Attagenus spp. , Auiacophora femoraiis, Biastophagus piniperda, Biitophaga undata, Bruchidius obtectus, Bruchus . such as B. ientis, B. p iso rum, B. rufimanus; Byctiscus betuiae, Callidiellum rufipenne, Caiiopi stria f/oridensis, Caiiosobruchus chinensis, Cameraria ohrideiia, Cassida nebuiosa, Cerotoma trifur- cata, Cetonia aurata, Ceuthorhynchus spp. such as C. assimi/is, C. napi; Chaetocnema tibialis, C/eonus mendicus, Conoderus spp. such as C. vespertinus; Conotracheius nenuphar, Cosmop olites spp., Costeiytra zeaiandica, Crioceris asparagi, Cryptoiestes ferrugineus, Cryptorhynchus iapathi, Ctenicera spp. such as C. destructor; Curcuiio spp., Cyiindrocopturus spp., Cycioceph- aia spp., Dactyiispa baiyi, Dectes texanus, Dermestes spp., Diabrotica spp. such as D. undec- impunctata, D. speciosa, D. iongicornis, D. semipunctata, D. virgifera; Diaprepes abbreviates, Dichocrocis spp., Diciadispa armigera, Diioboderus abderus, Diocaiandra frumenti (Diocaiandra stigmaticoiiis), Enaphaiodes rufu/us, Epiiachna spp. such as E. varivestis, E. vigintioctomacu- iata; Epitrix spp. such as E. hirtipennis, E. simiiaris; Eutheoia humiiis, Eutinobothrus brasi/iensis, Faustinus cubae, Gibbium psyiioides, Gnathocerus cornutus, Heiiuia undaiis, Heteronychus arator, Hyiamorpha eiegans, Hyiobius abietis, Hyiotrupes bajuius, Hypera spp. such as H. brun- neipennis, H. postica; Hypomeces squamosus, Hypothenemus spp., ips typographus, Lach- nosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp. such as L. biiineata, L. meianopus; Leptinotarsa spp. such as L. decemiineata; Leptispa pyg- maea, Limonius caiifornicus, Lissorhoptrus oryzophiius, Lixus spp., Luperodes spp., L yet us spp. such as L. bruneus; Liogenys fuscus, Macrodactyius spp. such as M. subspinosus; Maiadera matrida, Megapiatypus mutates, Megasceiis spp., Meianotus communis, Meiigethes spp. such as M. aeneus; Meioiontha spp. such as M. hippocastani, M. meioiontha; Metamasius hemip- terus, Microtheca s ., Migdoius spp. such as M. fryanus, Monocham us spp. such as M. aiter- natus; Naupactus xanthographus, Niptus ho/o/eucus, Oberia brevis, Oemona hirta, Oryctes rhi noceros, Oryzaephiius surinamensis, Oryzaphagus oryzae, Otiorrhynchus su/catus, Otiorrhyn- chus ovatus, Otiorrhynchus su/catus, Ouiema meianopus, Ouiema oryzae, Oxycetonia jucunda, Phaedon spp. such as P. brassicae, P. cochieariae; Phoracantha recurva, Phyiiobius pyri, Phyi- iopertha horticoia, Phyiiophaga spp. such as P. heiieri; Phyiiotreta spp. such as P. chrysoceph- aia, P. nemorum, P. strioiata, P. vittuia; Phyiiopertha horticoia, Popiiiia japonica, Premnotrypes spp., Psacothea hiiaris, Psyiiiodes chrysocephaia, Prostephanus truncates, Psyiiiodes spp., Pti- nus spp., Puiga saitona, Rhizopertha dominica, Rhynchophorus spp. such as R. biiiineatus, R. ferrugineus, R. paimarum, R. phoenicis, R. vuineratus; Saperda Candida, Scoiytus schevyrewi, Scyphophorus acupunctatus, Sitona iineatus, Si top hi/ us spp. such as S. granaria, S. oryzae, S. zeamais; Sphenophorus spp. such as S. ievis; Stegobium paniceum, Sternechus spp. such as S. subsignatus; Strophomorphus ctenotus, Symphyietes spp., Tanymecus spp., Tenebrio moiitor, Tenebrioides mauretanicus, T rib oiium spp. such as T. castaneum; Trogoderma spp., Tychius spp., Xyiotrechus spp. such as X. pyrrhoderus; and, Zabrus spp. such as Z. tenebri oides;

insects from the order of Diptera e.g. /leotes spp. such as A. aegypti, A. aibopictus, A. vexans; Anastrepha iudens, Anopheles spp. such as A. aibimanus, A. crucians, A. freeborni, A. gam- biae, A. ieucosphyrus, A. macuiipennis, A. minimus, A. quadrimacuiatus, A. sinensis; Bactro- cera invadens, Bibio hortuianus, Caiiiphora erythrocephaia, Caiiiphora vicina, Ceratitis capitata, Chrysomyia spp. such as C. bezziana, C. hominivorax, C. maceiiaria; Chrysops atianticus, Chrysops discaiis, Chrysops siiacea, Cochiiomyia spp. such as C. hominivorax; Contarinia spp. such as C. sorghicola; Cordylobia anthropophaga, Cuiex spp. such as C. nigripalpus, C. pipi- ens, C. quinquefasciatus, C. tarsalis, C. tritaeniorhynchus; Cu/icoides furens, Culiseta inornata, Culiseta melanura, Cute re bra spp., Dacus cucurbitae, Dacus oteae, Dasineura brassicae, Dasi- neura oxycoccana, Delia spp. such as D. antique, D. coarctata, D. piatura, D. radicum; Dermat- obia hominis, Drosophila s . such as D. suzukii, Fannia spp. such as F. canicuiaris; Gastraphi- ius spp. such as G. intestina/is; Geomyza tipunctata, Giossina spp. such as G. fuscipes, G. mor- sitans, G. paipaiis, G. tachinoides; Haematobia irritans, Hapiodipiosis equestris, Hippeiates spp., Hylemyia spp. such as H. piatura; Hypoderma spp. such as H. iineata; Hyppobosca spp., Hydreiiia phiiippina, Leptoconops torrens, Liriomyza spp. such as L. sativae, L trifoiii; Luciiia spp. such as L. caprina, L. cuprina, L. sericata; Lycoria pectoraiis, Mansonia titiiianus, Mayetioia spp. such as M. destructor; Musca spp. such as M. autumnaiis, M. domestica; Muscina stabu- ians, Oestrus spp. such as O. ovis; Opomyza fiorum, Oscineiia spp. such as O. frit; Orseoiia oryzae, Pegomya hysocyami, Phiebotomus argentipes, Phorbia spp. such as P. antiqua, P. brassicae, P. coarctata; Phytomyza gymnostoma, Prosimuiium mixtum, Psiia rosae, Psorophora coiumbiae, Psorophora discolor, Rhagoietis spp. such as R. cerasi, R. cingulate, R. indifferens, R. mendax, R. pomoneiia; Riveiiia quadrifasciata, Sarcophaga spp. such as S. haemorrhoidaiis; Simu/ium vittatum, Sitodipiosis moseiiana, Stomoxys spp. such as S. caicitrans; Tabanus spp. such as T. atratus, T. bovinus, T. iineoia, T. simi/is; Tannia spp., Thecodipiosis japonensis, Tip- uia oieracea, Tipuia paiudosa, and Wohifahrtia spp;

insects from the order of Thysanoptera, e.g. Baiiothrips biformis, Dichromothrips corbetti, Di- chromothrips ssp., Echinothrips americanus, Enneothrips fiavens, Frankiinieiia spp. such as F. fusca, F. occidentaiis, F. tritici; Heiiothrips spp., Hercinothrips femoraiis, Kakothrips spp., Micro- cephaiothrips abdominaiis, Neohydatothrips samayunkur, Pezothrips keiiyanus, Rhipiphoro- thrips cruentatus, Sci doth rips spp. such as S. citri, S. dorsalis, S. perseae; Stenchaetothrips spp, Taeniothrips cardamom) Taeniothrips inconsequens, 77?A/ s spp. such as T. imagines, T. hawaiiensis, T. oryzae, T. paimi, T. parvispinus, T. tabaci;

insects from the order of Hemiptera, e.g. Acizzia jamatonica, Acrosternum spp. such as A. hiiare; Acyrthosipon spp. such as A. onobrychis, A. pisum; Ade/ges lands, Ade/ges tsugae,

A deiphocoris spp., such as A. rapidus, A. superbus; Aeneoiamia spp., A gonoscena spp., Au- iacodhum soiani, Aieurocanthus wogiumi, Aieurodes spp., Aieurodicus disperses, Aieuroiobus barodensis, Aieurothrixus spp., Amrasca spp., Anasa tristis, Antestiopsis spp., Anuraphis car- dui, Aonidieiia spp., Aphanostigma piri, Aphiduia nastudii, Aphis spp. such as A. craccivora, A. fabae, A. forbesi, A. gossypii, A. grossuiariae, A. maidiradicis, A. pomi, A. sambuci, A. schnei- deri, A. spiraecoia; Arboridia apicaiis, Ari/us critatus, Aspidieiia spp., Aspidiotuss ., Atanus spp., Auiacaspis yasumatsui, Auiacodhum soiani, Bactericera cockereiii (Paratrioza cockereiii), Bern i si a spp. such as B. argentifoiii, B. tabaci (Aieurodes tabaci); Bliss us spp. such as B. ieu- copterus; Brachycaudus spp. such as B. cardui, B. heiichrysi, B. persicae, B. prunicoia; Brachy- co/us spp., Brachycoryne/ia asparagi, Brevicoryne brassicae, Cacopsyiia spp. such as C. fuigu- raiis, C. pyricoia (Psyiia piri); Caiiigypona marginata, Caiocoris spp., Campyiomma iivida, Capi- tophorus horni, Carneocephaia fuigida, Caveierius s^., Cerapiastes spp., Ceratovacuna ianig- era, Cerop/astes ceriferus, Cerosipha gossypii, Chaetosiphon fragaefolii, Chionaspis tega/ensis, Chiorita onukii, Chromaphis jugiandicoia, Chrysomphaius ficus, Cicaduiina mbiia, Cimex spp. such as C. hemipterus, C. iectuiarius; Coccomytiius haiii, Coccus spp. such as C. hesperidum,

C. pseudomagnoHarum, Corythucha arcuata, Creontiades di/utus, Cryptomyzus ribis, Chrysomphalus aonidum, Cryptomyzus ribis, Ctenarytaina spatulata, Cyrtopeltis notatus, Daibu- //ys spp., Dasynus piperis, Diateurodes spp. such as D. citrifoM; Dalbulus maidis, Diaphorina spp. such as D. citri; Diasp is spp. such as D. bromeliae; Dichelops furcatus, Diconocoris he- wetti, Doratis spp., Dreyfusia nordmannianae, Dreyfusia piceae, Drosicha s ., Dysaphis spp. such as D. ptantaginea, D. pyri, D. radicota; Dysautacorthum pseudoso/ani, Dysdercus spp. such as D. cingutatus, D. intermedius; Dysmicoccus spp., Edessa spp., Geocoris spp., Empo- asca spp. such as E. fabae, E. sotana; Epidiaspis teperii, Eriosoma spp. such as E. tanigerum,

E. pyri cola; Erythroneura spp., Eurygaster spp. such as E. integriceps; Eusce/is b/lobatus, Eu- schistus spp. such as E. heros, E. impictiventris, E. servus; Fiorinia theae, Geococcus coffeae, Gtycaspis brimbtecombei, Halyomorpha spp. such as H. halys; Heliopelt is spp., Homalodisca vitripennis (=H. coagulata), Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lactucae, lcerya spp. such as /. purchase; Idiocerus spp., Idioscopus spp., Laodelphax striate/lus, Lecanium spp., Lecanoideus f/occissimus, L epidosaphes spp. such as L. ulmi; Leptocorisa spp., Lepto- g/ossus phy/lopus, Lipaphis erysimi, Lygus spp. such as L. hesperus, L. lineolaris, L. pratensis; Maconellicoccus hirsutus, Marchalina hellenica, Macropes excavatus, Macrosiphum spp. such as M. rosae, M. a venae, M. euphorbiae; Macrosteles quadrilineatus, Mahanarva fimbriolata, Megacopta cribraria, Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari, Melanocallis (=Tinocallis) caryaefoliae, Me tea fie I la spp., Metopoiophium dirhodum, Moneiiia costaiis, Monei- i/opsis pecan/s, Myzocaiiis coryii, Murgantia s ., Myzus spp. such as M. ascaionicus, M. cera- si, M. nicotianae, M. persicae, M. varians; Nasonovia ribis-nigri, Neotoxoptera formosana, Neo- megaiotomus spp, Nephotettixs . such as N. maiayanus, N. nigropictus, N. parvus, N. vires- cens; Nezara spp. such as N. viriduia; Niiaparvata iugens, Nys/us button/, Oebaius spp. such as O. pugnax; Oncometopia spp., Orthezia praeionga, Oxycaraenus hyaiinipennis, Parabemisia myricae, Pariatoria spp., Parthenoiecanium spp. such as P. corni, P. persicae; Pemphigus s . such as P. bursarius, P. popuiivenae; Peregrinus maidis, Perkinsieiia saccharicida, Phenacoc- cus spp. such as P. aceris, P. gossypii; Phioeomyzus passerinii, Phorodon humuii, 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, Protopuivinaria pyri- formis, Psa/lus seriatus, Pseudacysta persea, Pseudaulacaspis pentagona, Pseudococcus spp. such as P. com stock!; Psylla spp. such as P. mall; Pteromalus spp., PuMnaria amygdali, PyriHa spp., Quadrasp/d/otus s pp., such as Q. perniciosus; Quesada gigas, Rastrococcus spp., Redu- vius senilis, Rhizoecus americanus, Rhodnius spp., Rhopaiomyzus ascaionicus, Rhopaiosi- phum spp. such as R. pseudobrassicas, R. insertum, R. maidis, R. padi; Saga tod es spp., Sahi- bergeiia singuiaris, Saissetia spp., Sappaphis maia, Sappaphis maii, Scaptocoris spp., Scaph- oides titanus, Schizaphis graminum, Schizoneura lanuginosa, Scotinophora spp., Se/enaspidus articu/atus, Sitobion avenae, Sogata spp., Sogateiia furcifera, So/ubea insuiaris, Sp/ss/st/ius festinus (=Stictocephaia festina), Stephanitis nashi, Stephanitis pyrioides, Stephanitis takeyai, Tenaiaphara maiayensis, Tetraieurodes perseae, Therioaphis maculate, Thyanta . such as T. accerra, T. perditor; Tibraca pp., Tomaspis spp., Toxoptera spp. such as T. aurantii; Triaieu- rodes spp. such as T. abutiionea, T. ricini, T. vaporariorum; Triatoma spp., Trioza s^., Typhio- cyba ., Unaspis spp. such as U. citri, U. yanonensis; and Viteus vitifoiii,

Insects from the order Hymenoptera, e.g. Acanthomyops interjectus, Athaiia rosae, Atta spp. such as A. capiguara, A. cephaiotes, A. cephaiotes, A. laevigata, A. robusta, A. sexdens, A. tex- ana, Bombus spp., Brachymyrmex s p p . , Camponotus spp. such as C. floridanus, C. pennsyi- vanicus, C. modoc; Cardiocondyla nuda, Chaiibion sp, Crematogaster spp., DasymutiHa occi- dentalis, Diprion s ., Doiichovespuia macuiata, Dorymyrmex spp., Dryocosmus kuriphiius, For mica spp., Hopiocampa spp. such as H. minuta, H. testudinea; iridomyrmex humiiis, Lasius spp. such as L niger, Linepithema humiie, Liometopum spp., Leptocybe invasa, Monomorium spp. such as M. pharaonis, Monomorium, Nyiandria fuiva, Pachycondyia chinensis, Paratrechina ion- gicornis, Para vespuia spp., such as P. germanica, P. pennsyivanica, P. vulgaris; Pheidoie spp. such as P. megacephaia; Pogonomyrmex spp. such as P. barbatus, P. caiifornicus, Po/istes ru- biginosa, Prenoiepis impairs, Pseudomyrmex gracilis, Scheiipron spp., Sirex cyaneus, So/enop- sis spp. such as S. geminata, S.invicta, S. moiesta, S. richteri, S. xyioni, Sphecius speciosus, Sphex spp., Tapi noma spp. such as T. meianocephaium, T. sessile; Tetramorium spp. such as T. caespitum, T. bicarinatum, Vespa spp. such as V. crabro; Vespuia . such as V. squamo sal; Wasmannia auropunctata, Xyiocopa sp;

Insects from the order Orthoptera, e.g. Acheta domesticus, Caiiiptamus itaiicus, Chortoicetes terminifera, Ceuthophi/us spp., Diastrammena asynamora, Dociostaurus maroccanus, Gryiio- taipa spp. such as G. africana, G. gryiiotaipa; Gryiius spp., Hierogiyphus daganensis,

Kraussaria anguiifera, Locusta spp. such as L. migratoria, L. pardaiina; Meianopius spp. such as M. bivittatus, M. femurrubrum, M. mexicanus, M. sanguinipes, M. spretus; Nomadacris sep- temfasciata, Oeda/eus senega/ensis, Scapteriscus spp., Schistocerca spp. such as S. ameri- cana, S. gregaria, Stemopeimatus 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 Ambiyomma spp. (e.g. A. americanum, A. variegatum, A. macuiatum), Argas spp. such as A. persicu), Boophiius spp. such as B. annuiatus, B. decoioratus, B. micropius, Dermacentor spp. such as D.siivarum, D. andersoni, D. variabiiis, Hyaiomma spp. such as H. truncatum, ixodes spp. such as /. ricinus, i. rubicundus, i. scapuiaris, i. hoiocycius, i. pacificus, Rhipicephaius sanguineus, Ornithodorus spp. such as O. moubata, O. hermsi, O. turicata, Orni- thonyssus bacoti, Otobius megnini, Dermanyssus gaiiinae, Psoroptes spp. such as P. ovis, Rhipicephaius spp. such as R. sanguineus, R. appendicuiatus, Rhipicephaius evertsi, Rhizogiy- phus spp., Sarcoptes spp. such asS. Scabiei, and Family Eriophyidae including Aceria spp. such as A. she/doni, A. anthocoptes, Acaiiitus spp., Acu/ops spp. such as A. iycopersici, A. pei- ekassi, Acu/us spp. such as A. schiechtendaii; Coiomerus vitis, Epitrimerus pyri, Phyiiocoptruta oieivora; Eriophytes rib is and Eriophyes spp. such as Eriophyes sheidoni, Family Tarsonemidae including Hemitarsonem us spp., Phytonemus paiiidus and Poiyphagotarsonemus iatus, Steno- tarsonemus spp. Steneotarsonemus spinki, Family Tenuipalpidae including Brevipalpus spp. such as B. Phoenicia, Family Tetranychidae including Eotetranychus spp., Eutetranych us spp., O/igonychus spp., Petrobia iatens, Tetranych us spp. such as T. cinnabarinus, T. evansi, T. kan- zawai, T, pacificus, T. phaseu/us, T. teiarius and T. urticae, Bryobia praetiosar, Panonychus spp. such as P. uimi, P. citri, Metatetranychus spp. and O/igonychus spp. such as O. pratensis, O. perseae, Vasates iycopersici, Raoieiia indica, Aam/Zj/Carpoglyphidae including Carpogiyphus spp./ Penthaieidae spp. such as Haiotydeus destructor, Family Demodicidae with species such as Demodex spp.; Family Trombicidea including Trombicuia spp.; Family Macronyssidae includ- ing Ornothonyssus spp.; Family Pyemotidae including Pyemotes tritici, Tyrophagus putrescen- tiaer, Family Acaridae including Acarus sira, Family Araneida including Latrodectus mactans, Tegenaria agrestis, Chiracanthium sp, Lycosa sp Achaearanea tepidariorum and Loxosce/es rec/usa,

Pests from the Phylum Nematoda, e.g. plant parasitic nematodes such as root-knot nema- todes, Meloidogyne spp. such as M. hapla, M. incognita, M. javanica; cyst-forming nematodes, Giobodera spp. such as G. rostochiensis; Heterodera spp. such as H. avenae, H. glycines, H. schachtii, H. trifoiii; Seed gall nematodes, Anguina spp.; Stem and foliar nematodes, Apheien- choides spp. such as A. besseyi; Sting nematodes, Beionoiaimus spp. such as B. iongicauda- tus; Pine nematodes, Bursapheienchus spp. such as B. iignicoius, B. xyiophiius; Ring nema- todes, Criconema spp., Criconemeiia spp. such as C. xenopiax and C. orna fa; and, Cricone- moides spp. such as Criconemoides inform is; Mesocriconema spp./ Stem and bulb nematodes, Dity tench us spp. such as D. destructor, D. dipsaci; Awl nematodes, Doiichodorus spp. /Spiral nematodes, Heiiocotyienchus mu/ticinctus; Sheath and sheathoid nematodes, Hemicyciiophora spp. and Hemicriconemoides spp./ Hirshmannieiia spp./ Lance nematodes, Hopioaimus spp./ False rootknot nematodes, Nacobbus spp./ Needle nematodes, Longidorus spp. such as L. eiongatus; Lesion nematodes, Pratyienchus spp. such as P. brachyurus, P. neg/ectus, P. pene trans, P. curvitatus, P. goodeyi; Burrowing nematodes, Radophoius spp. such as R. simi/is; Rhadophoius spp./ Rhodopho/us spp./ Reniform nematodes, Rotyienchus spp. such as R. ro- bustus, R. reniformis; Scuteiionema spp./ Stubby-root nematode, Trichodorus spp. such as T. obtusus, T. primitivus; Paratrichodorus spp. such as P. minor; Stunt nematodes, Tyienchorhyn- chusspp. such as T. ciaytoni, T. dubius; Citrus nematodes, Tyienchuius spp. such as T. semi- penetrans; \bay^t nematodes, Xiphinema s .; and other plant parasitic nematode species;

Insects from the order Isoptera, e.g. Caiotermes fiavicoiiis, Coptotermes spp. such as C. for- mosanus, C. gestroi, C. acinaciformis; Cornitermes cumuians, Cryptotermes spp. such as C. brevis, C. cavifrons; G/obitermes su/fureus, Heterotermes spp. such as H. aureus, H. iongiceps, H. tenuis; Leucotermes f/avipes, Odontotermes spp., incisitermes spp. such as /. minor, i.

Snyder, Marginitermes hubbardi, Mastotermes spp. such as M. darwiniensis Neocapritermes spp. such as N. opacus, N. parvus; Neotermes spp., Procorn itermes spp., Zootermopsis spp. such as Z. angustico/iis, Z. nevadensis, Reticu/itermes spp. such as R. hesperus, R. tibialis, R. speratus, R. fiavipes, R. grassei, R. iucifugus, R. santonensis, R. virginicus; Termes nataiensis, Insects from the order Blattaria, e.g. Biatta spp. such as B. orientaiis, B. lateralis; Biatteiia spp. such as B. asahinae, B. germanica; Leucophaea maderae, Panchiora nivea, Peripianeta spp. such as P. americana, P. austraiasiae, P. brunnea, P. fuiigginosa, P. japonica; Supeiia iongi- paipa, Parcobiatta pennsyivanica, Eurycotis fioridana, Pycnosceius surinamensis,

Insects from the order Siphonoptera, e.g. Cediopsyiia simples, Ceratophyiius spp., Cten- ocephaiides spp. such as C. fe/is, C. canis, Xenopsyiia cheopis, Puiex irritans, Trichodectes ca m ^' s, Tung a penetrans, and Nosopsy/ius fasciatus,

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

Pests from the class Chilopoda, e.g. Geophi/us spp., Scutigera spp. such as Scutigera coieop- trata,

Pests from the class Diplopoda, e.g. Bianiuius guttu/atus, Ju/us spp., Narceus spp.,

Pests from the class Symphyla, e.g. Scutigereiia immacuiata,

Insects from the order Dermaptera, e.g. Forficuia auricuiaria,

Insects from the order Collembola, e.g. Onychiurus spp., such as Onychiurus armatus, Pests from the order Isopoda, e.g. ArmadiHidium vulgare, Oniscus asellus, PorceMo scaber,

Insects from the order Phthiraptera, e.g. Damaiinia s ., Pediculus spp. such as Pedicuius hu- manus capitis, Pedicuius human us corporis, Pedicuius 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- ienopotes capiiiatus, Trichodectes spp.,

Examples of further pest species which may be controlled by compounds of fomula (I) include: from the Phylum Mollusca, class Bivalvia, e.g. Dreissena spp.; class Gastropoda, e.g. Arion spp., Biomphaiaria spp., Buiinus s ., Derocerass ., Gaiba spp., Lymnaea spp., Oncomeiania spp., Pomacea canaiiciata, Succinea spp. /from the class of the helminths, e.g. Ancyiostoma duodenaie, Ancyiostoma ceyianicum, Acyiostoma braziiiensis, Ancyiostoma spp., Ascaris iubri- coides, Ascaris spp., Brugia maiayi, Brugia timori, Bunostomum spp., Chabertia spp., Cionor- chis spp., Cooperia spp., Dicrocoeiium spp., Dictyocauius fiiaria, Diphyiiobothrium iatum, Dra- cuncu/us medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius ver- micuiaris, Facioia spp., Haemonchus spp. such as Haemonchus contortus; Heterakis spp., Hy- menoiepis nana, Hyostronguius spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyioides fueiieborni, Strongyioides stercora iis, Stronyioides spp., Taenia saginata, Taenia so/ium, Trichineiia spiralis, Trichineiia native, Trichineiia britovi, Trichi neiia neisoni,

Trichi neiia pseudopsira/is, Trichostronguius spp., Trichuris trichuria, Wuchereria bancrofti.

The compounds of the invention are suitable for use in treating or protecting animals against infestation or infection by parasites. Therefore, the invention also relates to the use of a corn- pound of the invention for the manufacture of a medicament for the treatment or protection of animals against infestation or infection by parasites. Furthermore, the invention relates to a method of treating or protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiti- cidally effective amount of a compound of the invention.

The present invention also relates to the non-therapeutic use of compounds of the invention for treating or protecting animals against infestation and infection by parasites. Moreover, the invention relates to a non-therapeutic method of treating or protecting animals against infesta- tion and infection by parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the invention.

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

The invention also relates to the non-therapeutic use of compounds of the invention for con- trolling or combating parasites. Moreover, the invention relates to a non-therapeutic method of combating or controlling parasites, which comprises applying to a locus a parasiticidally effec- tive amount of a compound of the invention.

The compounds of the invention can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits). Furthermore, the

compounds of the invention can be applied to any and all developmental stages. The compounds of the invention can be applied as such or in form of compositions comprising the compounds of the invention.

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

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

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

As used herein, the term "contacting" includes both direct contact (applying the com- pounds/compositions directly on the parasite, including the application directly on the animal or excluding the application directly on the animal, e.g. at it's locus for the latter) and indirect con- tact (applying the compounds/compositions to the locus of the parasite). The contact of the par- asite through application to its locus is an example of a non-therapeutic use of the compounds of the invention.

The term "locus" means the habitat, food supply, breeding ground, area, material or environ- ment 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 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, bit ing lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.

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

fleas (Siphonaptera), e.g. Ctenocephalides fe/is, Ctenocepha/ides cam ^' s, Xenopsy/ia cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus; cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, B latte I la asahinae, Peri plane ta am erica na, Peri plan eta japonica, Peri- pianeta brunnea, Peripianeta fuligginosa, Peripianeta australasiae, and Blatta oriental is; flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes a/bopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimacuia- tus, CaWphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atianticus, Cochiiomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia horn inis, Fannia canicularis, GasterophHus intestinalis, G/ossina morsitans, G/ossina pa I pa I is, G/ossina fuscipes, G/ossina tachinoides, Haematobia irritans, Hapiodipiosis equestris, Hippeiates spp., Hypoderma iineata, Leptoconops torrens, Lu cilia caprina, Lu cilia cuprina, Lu cilia sericata, Lycoria pectoral is, Manso- nia spp., Musca domestica, Muscina stabuians, Oestrus ovis, Phiebotomus argentipes, Psoro- phora columbiae, Psorophora discolor, ProsimuHum mixtum, Sarcophaga haemorrhoida/is, Sar- cophaga sp., Sim u Hum vittatum, Stomoxys caicitrans, Tabanus bovinus, Tabanus atratus, Taba- nus iineoia, and Tabanus simi/is; lice (Phthiraptera), e.g. Pedicuius humanus capitis, Pedicuius humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituii, Bovicoia bovis, Menopon gaiiinae, Menacanthus stramineus and Soienopotes capiiiatus; ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. ixodes scapuiaris, ixodes hoiocy- c/us, ixodes pad ficus, Rhiphicephaius sanguineus, Dermacentor andersoni, Dermacentor varia- biiis, Ambiyomma americanum, Ambryomma macuiatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssus gaiii- nae, Actinedida (Prostigmata) und Acaridida (Astigmata), e.g. Acarapis spp., Cheyietieiia spp., Ornithocheyietia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicuia spp.,

Listrophorus spp., Acarus spp., Tyrophagus spp., Caiogiyphus spp., Hypodectes spp., Pteroi- ichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., and Laminosioptes spp; Bugs (Heteropterida): Cimex iectuiarius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongyius ssp., and Ariius critatus; Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pedicuius spp., Phtirus spp., and Soienopotes spp.; Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicoia spp., Werneckieiia spp.,

Lepikentron spp., Trichodectes spp., and Feiicoia spp.; Roundworms Nematoda: Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichineiia spp.), /Trichuridae^ Trichuris spp., CapiHaria spp.; Rhabditida, e.g. Rhabditis spp., Strongyioides spp., Heiicephaiobus spp.; Strongylida, e.g. Strongyius spp., Ancyiostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongyius spp., Haemonchus contortus, Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocauius spp., Cyathostoma spp., Oesophagostomum spp., Stepha- nurus dentatus, Oiiuianus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, An cyiostoma spp., Uncinaria spp., Giobocephaius spp., Necator spp., Metastrongyius spp., Mueiierius capiHaris, Protostrongyius spp., Angiostrongyius spp., Pareiaphostrongyius spp., Ai- eurostrongy/us abstrusus, and Dioctophyma renaie; Intestinal roundworms (Ascaridida), e.g. Ascaris iumbricoides, Ascaris suum, Ascaridia gaiii, Parascaris equorum, Enterobius vermicu lar/ s (Threadworm), Toxocara can is, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi; Camallanida, e.g. Dracuncuius medinensis (guinea worm); Spirurida, e.g. Theiazia spp., Wu- chereria spp., Brugia spp., Onchocerca spp., DirofHari spp. a, Dipetaionema spp., Setaria spp., Eiaeophora spp., Spirocerca iupi, and Habronema spp.; Thorny headed worms (Acanthoceph- ala), e.g. Acanthocephaius spp., Macracanthorhynchus hirudinaceus and Oncicoia spp.; Plana r- ians (Plathelminthes): Flukes (Trematoda), e.g. Facioia spp., Fascio/oides magna, Paragonimus spp., Dicrocoeiium spp., Fascio/opsis busk/, Cionorchis sinensis, Schistosoma spp., Trichobii- harzia spp., Aiaria aiata, Paragonimus spp., and Nanocyetes spp:, Cercomeromorpha, in partic- ular Cestoda (Tapeworms), e.g. Diphyiiobothrium spp., Tenia spp., Echinococcus spp., Dipyiid- ium caninum, Muiticeps spp., Hymenoiepis spp., Mesocestoides spp., Vampiroiepis spp., Mon- iezia spp., Anopiocephaia spp., Sirometra spp., Anopiocephaia spp., and Hymenoiepis 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, rab- bits, 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 pre- ferred 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/com- positions 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, tar- get species, mode of application, and the like.

Generally, it is favorable to apply the compounds of the invention in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.

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, sus- pensions, 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, e.g. by intraruminal, intramuscular, intravenous or subcutaneous injection. The formula I compounds may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injec- tion. Alternatively, the formula I compounds may be formulated into an implant for subcutaneous administration. In addition the formula I compound may be transdermally administered to ani- mals. 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 usu- ally contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the formula I corn- pound. In addition, the formula I compounds may be formulated as ear tags for animals, particu- larly 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, bo- luses, capsules; aerosols and inhalants, and active compound-containing shaped articles.

Compositions suitable for injection are prepared by dissolving the active ingredient in a suita- ble solvent and optionally adding further auxiliaries such as acids, bases, buffer salts, preserva- tives, 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 dilu tion 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 nec- essary.

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 corn- pound penetrating the skin and acting systemically. Pour-on formulations are prepared by dis solving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries 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 corn- pound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the sol- vent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabi- lizers, 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 suspend- ing the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxi- dants, light stabilizers. Suitable suspending agents, and suitable other auxiliaries for suspen- sions 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 auxil- iaries 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 invention.

Ready-to-use preparations contain the compounds acting against parasites, preferably ecto- parasites, 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 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.

Examples

A. Preparation examples

With appropriate modification of the starting materials, the procedures given in the synthesis description were used to obtain further compounds I. The compounds obtained in this manner are listed in the table that follows, together with physical data.

The products shown below were characterized by the masses ([m/z]) and retention time (RT; [min.]) determined by HPLC-MS spectrometry.

HPLC-MS = high performance liquid chromatography-coupled mass spectrometry;

HPLC method: HPLC method: Phenomenex Kinetex 1.7 pm XB-C18 100A; 50 x 2.1 mm; mo- bile phase: A: water + 0.1 % trifluoroacetic acid (TFA); B: acetonitrile; gradient: 5-100% B in 1.50 minutes; 100% B 0.25 min; flow: 0.8-1 .Oml/min in 1.51 minutes at 60°C. MS: ESI positive, m/z 100-700.

The synthesis of (1 RS,3RS)-2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropanecarbo xylic acid and (1 RS,3RS)-2,2-dichloro-3-[4-fluoro-3-(trifluoromethyl)phenyl]c yclopropanecarboxylic acid was performed in analogy to WO 2016/168056, WO 2016/168058, WO 2016/168059, and WO2018/071327.

Example 1 : Synthesis of 6-chloro-N-cyclopropyl-2-[2,2-dichloro-3-(3,5-dichlorophenyl )cyclopro- pyl]-1 -ethyl-benzimidazole-5-carboxamide [1-2-1 ].

Step 1 : 2-chloro-N-cyclopropyl-5-[[2,2-dichloro-3-(3,5-dichloropheny l)cyclopropanecarbonyl]- amino]-4-(ethylamino)benzamide: To a solution of (1 RS,3RS)-2,2-dichloro-3-(3,5-dichloro- phenyl)cyclopropanecarboxylic acid (500 mg, 1 .67 mmol) in CH2CI2 (5.0 ml.) at ambient temperature was sequentially added 5-amino-2-chloro-N-cyclopropyl-4-(ethylamino)benzamide (508 mg, 2.00 mmol) [cf. WO 20121 19984], bromotripyrrolidinophosphonium hexafluoro- phosphate (“PyBrop”) (932 mg, 2.00 mmol), and iP^NEt (905 mg, 7.00 mmol). The resulting reaction mixture was stirred at ambient temperature over night, before it was concentrated under reduced pressure and purified by column chromatography (EtOAc/cyclohexane 0:100 to 45:55, gradient) to afford the title compound (603 mg, 68%).

LC-MS: Mass calc for C ₂₂ H ₂ oN ₃ 0 ₂ Cls ⁺ [(M) ⁺ ] 535.7, found 535.9; R _t = 1 .309 min; ¹ H NMR (400 MHz, CDCI3, RT) d 10.04 (s, 1 H), 7.33 (t, J = 1.9 Hz, 1 H), 7.23 (s, 1 H), 7.20 (d, J = 1.7 Hz, 2H), 6.87 (d, J = 3.5 Hz, 1 H), 6.40 (s, 1 H), 4.35 (br. s, 1 H), 3.53 (d, J = 8.2 Hz, 1 H), 3.32 (d, J = 8.3 Hz, 1 H), 3.08 (app. p, J = 7.1 Hz, 2H), 2.90 (app. tq, J = 7.4, 3.8 Hz, 1 H), 1 .26 (t, J = 7.2 Hz,

3H), 0.89 - 0.77 (m, 2H), 0.68 - 0.56 (m, 2H). Step 2: Synthesis of 6-chloro-N-cyclopropyl-2-[2,2-dichloro-3-(3,5-dichlorophenyl )cyclopropyl]- 1 -ethyl-benzimidazole-5-carboxamide [1-2-1]: In a 10 mL microwave vial, the above 2-chloro-N- cyclopropyl-S- ^-dichloro-S-^S-dichloropheny cyclo-'propane-'carbonyll-'aminoH-iethyla- mino)benzamide (300 mg, 0.560 mmol) was dissolved in 1 ,2-dichloroethane (3.0 mL) and tri- fluoroacetic acid (0.30 mL), the vial was sealed, and then heated at 80 °C in a microwave reac- tor for 15 minutes. After that time, the resulting reaction mixture was allowed to cool to ambient temperature, quenched with Na ₂ C0 ₃ solution (sat. aqueous, 10 mL), and the aqueous phase was extracted with CH2CI2 (3 x 5 mL). The combined organic extracts were dried over Na ₂ S0 ₄ , filtered, and concentrated under reduced pressure. Purification by column chromatography (EtOAc/cyclohexane 0:100 to 55:45, gradient) afforded the title compound (132 mg, 43%)

LC-MS: Mass calculated for C ₂₂ Hi ₈ N ₃ 0Cl ₅ ⁺ [(M+H) ⁺ )] 517.7, found 517.8; RT= 1.313 min;

¹ H NMR (500 MHz, CDCI ₃ , RT) d 7.89 (s, 1 H), 7.38 (s, 1 H), 7.37 (t, J= 1 .7 Hz, 1 H), 7.31 (d, J = 1 .9 Hz, 2H), 6.28 (d, J= 3.3 Hz, 1 H), 4.36 (qd, J= 7.4, 5.0 Hz, 2H), 3.98 (d, J= 8.1 Hz, 1 H), 3.21 (d, J= 8.1 Hz, 1 H), 2.94 (tq, J= 7.2, 3.7 Hz, 1 H), 1 .59 (t, J= 7.3 Hz, 3H), 0.92 - 0.82 (m, 2H), 0.69 - 0.59 (m, 2H).

Table C.1 - Compounds of formula 1.1

00 o

x> The given isomer in at least 85% by weight

# denotes the connection to the remainder of the molecule

II. Evaluation of pesticidal activity:

The activity of the compounds of formula I of the present invention can be demonstrated and evaluated by the following biological test.

Biological examples

If not otherwise specified, the test solutions are prepared as follow:

The active compound is dissolved at the desired concentration in a mixture of 1 :1 (vokvol) dis tilled water : acteone. The test solution is prepared at the day of use.

B.1 Caenorhabditis elegans

For evaluating control of Caenorhabditis elegans through contact or systemic means the test unit consisted of 96-well-microtiter plates containing a liquid diet.

The compounds or mixtures were formulated using a solution containing 75% water and 25% DMSO. Different concentrations of formulated compounds were sprayed into the microtiter plate wells at 5pl per well, using a custom built micro atomiz-er, at two replica-tions. Mixed instar 60- 100 C. elegans were transferred into the micro-titer plate wells. After application, the nematodes were incubated at 18 + 1 °C, 70 + 5 % RH for 4 days. Nematode motility (mortality) was then vis- ually assessed.

In this test compounds 1-1-1 , 1-1-2, 1-1-4, and 1-1-5, resp., at 2500 ppm showed over 50% mortality in comparison with untreated controls.

B.2 Yellow fever mosquito {Aedes aegypti)

For evaluating control of yellow fever mosquito (Aedes aegypti) the test unit consisted of 96- well-microtiter plates containing 200mI of tap water per well and 5-15 freshly hatched A. aegypti larvae.

The active compounds were formulated using a solution containing 75% (v/v) water and 25% (v/v) DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect diet at 2.5mI, using a custom built micro atomizer, at two replica-tions.

After application, microtiter plates were incubated at 28 + 1 °C, 80 + 5 % RH for 2 days. Larval mortality was then visually assessed.

In this test compounds 1-1-1 , 1-1-4, and 1-1-5, resp., at 2500 ppm showed over 50% mortality in comparison with untreated controls.

B.3 Boll weevil (Anthonomus grandis)

For evaluating control of boll weevil (Anthonomus grandis) the test unit consisted of 96-well- microtiter plates containing an insect diet and 5-10 A. grandis eggs.

The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 5 mI, using a custom built micro atomizer, at two replications.

After application, microtiter plates were incubated at about 25 + 1 °C and about 75 + 5 % rela- tive humidity for 5 days. Egg and larval mortality was then visually assessed.

In this test compounds 1-1-1 , 1-1-2, 1-1-4, and 1-1-5, resp., at 2500 ppm showed over 50% mortality in comparison with untreated controls. B.4 Green Peach Aphid (Myzus persicae)

For evaluating control of green peach aphid {Myzus persicae) through systemic means the test unit consisted of 96-well-microtiter plates containing liquid artificial diet under an artificial mem brane.

The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were pipetted into the aphid diet, us- ing a custom built pipetter, at two replications.

After application, 5 - 8 adult aphids were placed on the artificial membrane inside the microtiter plate wells. The aphids were then allowed to suck on the treated aphid diet and incubated at about 23 + 1 °C and about 50 + 5 % relative humidity for 3 days. Aphid mortality and fecundity was then visually assessed.

In this test compounds 1-1-1 at 2500 ppm showed over 50% mortality in comparison with un- treated controls.

B.5 Tobacco budworm {He/iothis virescens)

For evaluating control of tobacco budworm {He/iothis virescens) the test unit consisted of 96- well-microtiter plates containing an insect diet and 15-25 H. virescens eggs.

The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 10 pi, using a custom built micro atomizer, at two replications.

After application, microtiter plates were incubated at about 28 + 1 °C and about 80 + 5 % rela- tive humidity for 5 days. Egg and larval mortality was then visually assessed.

In this test compounds 1-1-1 , 1-1-4, and 1-1-5, resp., at 2500 ppm showed over 50% mortality in comparison with untreated controls.

B.6 Diamond back moth (Plutella xylostella)

The active compound was dissolved at the desired concentration in a mixture of 1 :1 (vokvol) distilled water : aceteone. Surfactant (Kinetic HV) was added at a rate of 0.01 % (vol/vol). The test solution was prepared at the day of use.

Leaves of cabbage were dipped in test solution and air-dried. Treated leaves were placed in petri dishes lined with moist filter paper and inoculated with ten 3rd instar larvae. Mortality was recorded 72 hours after treatment. Feeding damages were also recorded using a scale of 0- 100%.

In this test compounds 1-1-1 , and 1-1-5, resp., at 300 ppm showed over 75% mortality in com- parison with untreated controls