WO2022053453A1 - Azole carboxamide as pest control agents - Google Patents

Abstract

The invention relates to novel compounds of formula (I), wherein A, V, R1 and R2 have the above mentioned meaning, and to their use for controlling animal pests, in particular arthropods and especially insects and arachnids.

Description

Azolecarboxamides as pest control agents

The present invention relates to new azolecarboxamides, processes for their preparation and their use for controlling animal pests, especially arthropods and in particular insects and arachnids.

Certain triazole and pyrazole carboxamides with an insecticidal effect are already known (WO2020083733). Furthermore, azole carboxamides or azole caroxamides that differ greatly in structure have been described (WO2019121159, WO2018177781, WO2013116053). However, some of the active compounds already known according to the above-mentioned documents have disadvantages in their use, either that they have only a narrow range of use or that they do not have a satisfactory insecticidal effect.

Modern insecticides and acaricides have to meet many requirements, for example with regard to the level, duration and breadth of their effect and possible use. Questions of toxicity, the protection of beneficial insects and pollinators, the environmental properties, the amounts applied, the ability to combine them with other active ingredients or formulation aids play a role, as well as the question of the effort required to synthesize an active ingredient, and resistances can also occur, just to name a few parameters. For all of these reasons alone, the search for new crop protection agents cannot be considered complete, and there is a constant need for new compounds with properties which are improved, at least in relation to individual aspects, compared to the known compounds.

It was an object of the present invention to provide compounds for use in combating animal pests, which supplement the spectrum of pesticides from various aspects.

Surprisingly, it has now been found that certain new azolecarboxamides have advantages over the already known compounds, for example better biological or ecological properties, broader application methods, better insecticidal, acaricidal action and good compatibility with useful plants. The new azolecarboxamides can be used in combination with other agents to improve the effectiveness, in particular against insects that are difficult to control. The new compounds according to the invention have not been disclosed hitherto.

The present invention therefore relates to new compounds of the formula (I) wherein (embodiment 1-1)

A is N or CR ^A ; stands by

R ^A is H, halogen, cyano, nitro, SF5, NR ^d R ^e , OR ^a , S(O) _n R ^a or SC>2NR ^b R ^c ; or for Ci-Ce-alkyl, C2-Cg-alkenyl, C2-Cg-alkynyl or CACACycloalkyl. each of which can be unsubstituted or substituted once to 13 times with halogen and/or optionally with 1 to 3 R ^f ;

V is -C(Q ¹ )NR ^V1 R ^V2 ; stands by

R ^V1 is Ci-Cg-alkyl, Cz-Cg-alkenyl, Cz-Cg-alkynyl, C ₃ -C ₇ -cycloalkyl, C ₅ -C ₇ -cycloalkenyl or saturated C ₃ -C ₇ -heterocyclyl, all of which are unsubstituted can be, or can ^optionally be substituted once to 13 times with halogen and/or with 1 to 2 Rh;

R ^V2 for H; or for Ci-Cg-alkyl, C ₂ -Cg-alkenyl, C ₂ -Cg-alkynyl, Ci-Cg-alkoxy, C ₃ -C ₇ -cycloalkyl or Cs-C ₇ -cycloalkenyl, all unsubstituted or simple substituted up to 13 times with halogen and/or optionally with 1 to 2 R ^g ; or

R ^V1 and R ^V2 together with the nitrogen atom to which they are attached stand for a saturated, partially saturated or aromatic heterocycle having 3 to 7 ring atoms which is optionally interrupted by further heteroatoms and/or by one or two C=O groups and which ^is unsubstituted in each case or can be substituted once to seven times by halogen and/or optionally by 1 to 2 Rh;

^R1 is H; or for Ci-Cg-alkyl, C ₂ -Cg-alkenyl, C ₂ -Cg-alkynyl, C ₃ -C ₇ -cycloalkyl, Ci-Cg-alkyl carbonyl, C ₃ -C ₇ -cycloalkylcarbonyl, Ci-Cg- Alkoxycarbonyl, C ₃ -C ₇ -cycloalkoxyylcarbonyl, Ci-Cg -alkylsulfonyl or C ₃ -C ₇ -cycloalkylsulfonyl, each of which can be unsubstituted, or mono- to 13-fold with halogen and/or optionally with 1 to 2 R ^h may be substituted;

R ² represents the substructure of the general formula -XYZ; stands by X is phenyl or a 5- or 6-membered heteroaromatic ring each unsubstituted or substituted by 1 to 3 R ^x ; each is included

R ^x are independently halogen, cyano, nitro, C(Q ¹ )R ^a , C(O)OR ^a , C(Q ¹ )NR ^b R ^c , NR ^d R ^e , OR ^a , S(O) _n R ^a or SO ₂ NR ^b R ^c ; or for Ci-Cg-alkyl, C ₂ -C6-alkenyl, C ₂ - Cg-alkynyl or C3-C?-cycloalkyl, each unsubstituted or mono- to 13-substituted by halogen and/or optionally by 1 to 3 R ^f ;

Y for - CR ^Y1 =N- where N is bonded to Z, or for

-NR ^Y2 -C(=Q ^Y )-, where C is bonded to Z; each is included

R ^Y1 and R ^Y2 for H; or for Ci-Cg-alkyl, C ₂ -Cg-alkenyl, C ₂ -Cg-alkynyl or C3-C ₂ -cycloalkyl, all unsubstituted or substituted by 1 to 7 ^RY11 ; each is included

R ^Y11 independently for halogen, cyano, Ci-C4-alkyl, C3-Cg-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, or Ci-C4-haloalkoxy;

Q ^{Y is} O or S;

dabei ist # der Anknüpfungspunkt zu Y und dabei steht jedes Z for the fragments of the general formula (A1), (A2) or (A3);

where # is the connecting point to Y and where each stands

T for O or S;

R ^Z1 independently represent a 5- to 10-membered aromatic or heteroaromatic ring or a bicyclic ring system, each unsubstituted or substituted by 1 to 4 R ^Z11 ; each is included

R ^Z11 independently represent halogen, cyano, nitro, S . C(Q ¹ )R ^a , C(O)OR ^a , C(Q ¹ )NR ^b R ^c , NR ^{d Re} , OR ^a , S(O) _n R ^a or SO ₂ NR ^b R ^c ; or for Ci-Cg-alkyl, C ₂ -Cg- alkenyl, C ₂ -Cg-alkynyl or C3-C?-cycloalkyl, all unsubstituted or substituted by 1 to 5 R ^zla ; or phenyl or a 5- or 6-membered heteroaromatic ring each unsubstituted or substituted by 1 to 3 R ^zla ; or two adjacent R ^Z11 together form an unsubstituted or 1 to 6 R ^zla substituted linear Cs-Cs-alkylene group, where independently from one another 1 CH ₂ unit can be replaced by carbonyl and 1 to 2 CH ₂ units by O, S, NH or N(CH ₃ ); each is included

R ^zla for halogen, cyano, Ci-Ci-alkyl, Ci-C4-alkoxy, Ci-Ci-thioalkyl, Ci-C4-haloalkyl or Ci-C4-haloalkoxy;

R ^Z2 , R ^Z2a and R ^Z3 independently represent H; or for C(O)R ^a , C(O)OR ^a , C(O)NR ^b R ^c , S(O) _n R ^a ; or for C 1 -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl or C ₃ -C ₇ -cycloalkyl, each unsubstituted or substituted by 1 to 5 R ^Z21 ; or phenyl, benzyl or a 5- or 6-membered heteroaromatic ring, each unsubstituted or substituted by 1 to 4 R ^Z21 ; each is included

R ^Z21 are independently halogen, cyano, nitro, SFs, C(Q')R ^a . C(O) ^ORa , ^{CfQ1 ) NRb} Rc . NR ^d R ^e , OR ^a , S(O) _n R ^a or SO ₂ NR ^b R ^c ; or for Ci-C ₆ alkyl, Ci-C ₆ haloalkyl, C ₂ -Cg alkenyl, CS-Cg alkynyl or C ₃ -C ₇ cycloalkyl; or

R ^Z2 and R ^Z3 together with the TCN moiety form a 5- to 7-membered ring; the R ^Z2 -R ^Z3 ring members consist of carbon atoms and optionally 1 oxygen or sulfur or nitrogen atom; the heteroatom is not directly bonded to T; up to 2 carbon atom ring members can independently consist of C(=O) and C(=S) and the sulfur atom ring member can consist of S, S(O) or S(O) ₂ ; where this R ^Z2 -R ^Z3 unit is unsubstituted or substituted by 1 to 5 R ^Z21 ; each is included

R ^Z21 independently of one another for halogen, hydroxy, cyano, Ci-Cg-alkyl, C ₃ -Cg-cycloalkyl, Ci-Cg-haloalkyl, Ci-C4-alkenyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy; or for spirocyclically bonded heterocyclyl having 2 to 7 ring atoms, where 1 to 2 oxygen atoms are present as heteroatoms; or

R ^Z2a and a second R ^Z2a together with the NCN moiety form a 5- to 7-membered ring; the R ^Z2a -R ^Z2a ring members consist of carbon atoms and up to 2 heteroatoms, which can be selected independently from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms; up to 2 carbon atom ring members can independently consist of C(=O) and C(=S) and the sulfur atom ring member can consist of S, S(O) or S(O) ₂ ; where this R ^Z2 -R ^Z3 unit is unsubstituted or substituted by 1 to 5 R ^Z21 ; each is included R ^a independently for Ci-Cg-alkyl, C's-G, -cycloalkyl. C2-Cg-alkenyl or C2-Cg-alkynyl, all of which can be unsubstituted or substituted once to 13 times with halogen and/or optionally with 1 to 3 R ^f ; or phenyl unsubstituted or substituted by 1 to 5 R ^g ;

R ^b and R ^c independently represent H; or for Ci-Cg-alkyl, GG-cycloalkyl. C2-Cg-alkenyl or C2-Cg-alkynyl, each of which can be unsubstituted or substituted once to 13 times with halogen and/or optionally with 1 to 3 R ^f ; or R ^b and R ^c together form a 3- to 7-membered ring;

R ^d and R ^e are independently H, C(Q')R ^a . C(O) ^ORa ; or for Ci-Cg-alkyl, GG-cycloalkyl. C2-Cg-alkenyl or C2-Cg-alkynyl, all of which can be unsubstituted or substituted once to 13 times with halogen and/or optionally with 1 to ₃ R ^f ; or phenyl unsubstituted or substituted by 1 to 5 R ^g ; or R ^d and R ^e together form a 3- to 7-membered ring;

R ^f are independently halogen, cyano, nitro, GG-cycloalkyl. Ci-C4 alkoxy, C1-C4 haloalkoxy, Ci-C4 alkylthio, Ci-C4 haloalkylthio, Ci-C4 alkylsulfmyl, Ci-C4 haloalkylsulfinyl, Ci-C4 alkylsulfonyl, Ci-C4 haloalkylsulfonyl, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl; or phenyl or a 5- or 6-membered heteroaromatic ring each unsubstituted or substituted with 1 to 7 R ^g ;

R ^g independently for halogen, cyano, nitro, Ci-C4-alkyl, GG-cycloalkyl. C1-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy, Ci-C4 alkylthio, Ci-C4 haloalkylthio, C1-C4 alkylsulfmyl, Ci-C4 haloalkylsulfmyl, Ci-C4 alkylsulfonyl, Ci-C4-haloalkylsulfonyl, C1-C4-alkyl carbonyl or Ci-C4-alkoxycarbonyl;

R ^h are independently halogen, cyano, nitro, hydroxy, SF5, OSO2FV. ^{SO2NRb Rc} , N(Rd )(Re ), ^C (Q ^' ) ^{NRb Rc} . NCR^ Q^R ³ , C(O)R ^a , OC(O)R ^a or =Q ² ; or for Ci-C4- _alkyl , G-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfmyl, Ci-C4-alkylsulfonyl, GG-cycloalkyl. spirocyclically bound C2-Cg-cycloalkyl, spirocyclically bound heterocyclyl with 3 to 7 ring atoms, GG-cycloalkylthio. GG-cycloalkoxy. Cß-Cg-cycloalkylsulphinyl or GG-cycloalkylsulfonyl. each of which can be unsubstituted or substituted once to 13 times with halogen and/or optionally with 1 to 2 R ^g ; or phenyl or a 4- to 7-membered saturated, partially saturated or aromatic heterocycle having 1 to 4 heteroatoms, all of which may be unsubstituted or substituted once to 5 times by halogen and/or optionally by 1 to 2 R ^g be able;

Q ¹ independently represents O, S, N0R ^a or NCN;

Q ² are independently O or N0R ^a ; n are independently 0, 1 or 2.

Preferred (embodiment 2-1) are the compounds of the formula (I) in which

A is N or CR ^A ; stands by

R ^A is H, halogen, cyano or SF5; or for Ci-C4-alkyl, C2-C4-alkenyl, C2-Cg-alkynyl or CAG-cycloalkyl. each of which may be unsubstituted, or may be substituted one to seven times with halogen and/or optionally with an R ^f ;

V is -C(Q ¹ )NR ^V1 R ^V2 ; stands by

R ^V1 for Ci-C ₆ alkyl, C ₂ -C ₆ alkenyl, Cz-Cg alkynyl, C ₃ -C ₇ cycloalkyl, C ₅ -C ₇ cycloalkenyl or a saturated C ₃ -C ₇ heterocyclyl, each of which can be ^{unsubstituted} or optionally substituted once to five times with halogen and/or with 1 to 2 Rh;

R ^V2 for H; or for Ci-C ₆ -alkyl, C ₂ -C6-alkenyl, C ₂ -C6-alkynyl, Ci-Cg-alkoxy, C ₃ -C ₇ -cycloalkyl or Cs-C ₇ -cycloalkenyl all unsubstituted or simple substituted up to five times with halogen and/or optionally with 1 to 2 R ^g ; or

R ^V1 and R ^V2 together with the nitrogen atom to which they are attached represent a heterocycle from the series U-01 to U-06

U-01 and U-02 U-03 U-04 U-05 U-06 where all U-01 to U-06 can each be unsubstituted or optionally substituted once to 5 times with halogen and/or optionally with 1 to 2 ^rows

R ¹ for H; stands for Ci-C4-alkyl, C2-C4-alkenyl, C2-Cg-alkynyl or C ₃ ^-Cg -cycloalkyl, all of which may be unsubstituted in each case, or substituted one to five times by halogen and/or optionally by Ibis 2 Rh could be;

R ² represents the substructure of the general formula -XYZ; stands by

X is phenyl, pyridyl, pyrimidyl, pyridazinyl or thienyl, each unsubstituted or substituted by 1 to 3 R ^x ; stands by R ^x are independently halogen, cyano, nitro, C(Q ¹ )R ^a , C(O)OR ^a ; or for Ci-C ₄ alkyl, C ₂ -C ₄ alkenyl, Ci-C ₄ alkoxy, C ₂ -Cg alkynyl or C ₃ -Cg cycloalkyl, all unsubstituted or substituted by 1 to 3 R ^f ;

Y for - CR ^Y1 =N- where N is bonded to Z, or for

-NR ^Y2 -C(=Q ^Y )-, where C is bonded to Z; each is included

R ^Y1 and R ^Y2 for H; or for Ci-C-ralkyl, C2-Cg-alkenyl, C2-C4-alkynyl or G-CS-cycloalkyl, all unsubstituted or substituted by 1 to 3 R ^Y11 ; each is included

R ^Y11 independently represent halogen, cyano, Ci-C-ralkyl, C ₃ -Cg-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy;

Q ^Y for O or S;

dabei ist # der Anknüpfungspunkt zu Y und dabei steht jedes Z for the fragments of the general formula (A1), (A2) or (A3);

where # is the connecting point to Y and where each stands

T for O or S;

R ^Z1 is phenyl unsubstituted or substituted by 1 to 4 R ^Z11 ; each is included

R ^Z11 independently represent halogen, cyano, nitro, S . C(Q ¹ )R ^a , C(O)OR ^a , C(Q ¹ )NR ^b R ^c , NR ^{d Re} , OR ^a , S(O) _n R ^a or SO ₂ NR ^b R ^c ; or for Ci-Cg-alkyl, C ₂ -Cg- alkenyl, C2-Cg-alkynyl or G-Cv-cycloalkyl. all each unsubstituted or substituted by 1 to 5 R ^zla ; each is included

R ^zla for halogen, cyano, C'i-C ₃ -alkyl. Ci-C ₃ alkoxy, C1-C3 thioalkyl, Ci C's haloalkyl or Ci-C ₃ haloalkoxy;

R ^Z2 , R ^Z2a and R ^Z3 are independently H; or for C(O)R ^a , C(O)OR ^a , C(O)NR ^b R ^c , S(O) _n R ^a ; or for Ci-Cg-alkyl, Cz-Cg-alkenyl, C -Cg-alkmyl or C ₃ -C ₆ -cycloalkyl, all unsubstituted or substituted by 1 to 4 R ^Z21 ; or for phenyl or benzyl all in each case unsubstituted or substituted by 1 to 3 R ^Z21 ; each is included R ^Z21 independently for halogen, cyano, nitro, SF5, C(Q')R ^a . C(O)OR ^a , CCQ^NR^ ⁰ , NR ^{d Re} , OR ^a , S(O) _n R ^{a ,} or SO ₂ NR ^b R ^c ; or for Ci-C ₄ alkyl, C1-C4 haloalkyl, C1-C4 alkenyl, C2-C ₄ alkynyl or Cs-Cg-cycloalkyl; or

R ^Z2 and R ^Z3 together with the TCN moiety form a 5- to 7-membered ring; the R ^Z2 -R ^Z3 ring members consist of carbon atoms; up to 2 carbon atom ring members can independently consist of C(=O) and C(=S); wherein said R ^Z2 -R ^Z3 moiety is unsubstituted or substituted with from 1 to 4 R ^Z21 , where each is

R ^Z21 independently for halogen, hydroxy, cyano, Ci-Cg-alkyl, G-Cg-cycloalkyl, Ci-Cg-haloalkyl, Ci-C ₄ -alkenyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy; or

R ^Z2a and a second R ^Z2a together with the NCN moiety form a 5- to 7-membered ring; the R ^Z2a -R ^Z2a ring members consist of carbon atoms; up to 2 carbon atom ring members can independently consist of C(=O) and C(=S); this R ^Z2 -R ^Z3 unit is unsubstituted or substituted by 1 to 4 R ^Z21 ; each is included

R ^a independently for Ci-Cg-alkyl, G-Cg-cycloalkyl. C -Cg -alkcnyl or C -Cg -alkynyl. each of which can be unsubstituted or substituted once to five times by halogen and/or optionally by an R ^f ; or phenyl unsubstituted or substituted by 1 to 3 R ^g ;

R ^b and R ^c are independently H; or for Ci-Cg-alkyl, G-Cg-cycloalkyl. C -Cg -alkcnyl or C ₂ -Cg -alkynyl, all of which can be unsubstituted or substituted once to 13 times with halogen and/or optionally with 1 to 2 R ^f ; or R ^b and R ^c together form a 3- to 7-membered ring;

R ^d and R ^e are independently H, C (Q ¹ )R ^a . C(O) ^ORa ; or for Ci-Cg-alkyl, G-Cg-cycloalkyl. C ₂ -Cg-alkenyl or C ₂ -Cg-alkynyl, each of which can be unsubstituted or substituted once to five times with halogen and/or optionally with 1 to 2 R ^f ; or phenyl unsubstituted or substituted by 1 to 3 R ^g ; or R ^d and R ^e together form a 3- to 7-membered ring;

R ^f are independently halogen, cyano, nitro, G-Cg-cycloalkyl. Ci-C ₄ -alkoxy, C1-C4-haloalkoxy, Ci-C ₄ -alkylthio, Ci-C ₄ -haloalkylthio, Ci-C ₄ -alkylsulfmyl, Ci-C ₄ -haloalkylsulfinyl, Ci-C ₄ -alkylsulfonyl, Ci-C ₄ -haloalkylsulfonyl, C1-C4 -alkylcarbonyl or Ci-C ₄ -alkoxycarbonyl; or phenyl or pyridyl, or a 5- or 6-membered heteroaromatic ring, each unsubstituted or substituted with 1 to 3 R ^g ; R ^g are independently halogen, cyano, nitro, Ci-C4-alkyl, Cs-Cg-cycloalkyl, C1-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4 -Haloalkylthio, C1-C4-AI kylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, C1-C4-AI kylcarbonyl or Ci-C4-alkoxycarbonyl;

R ^h are independently halogen, cyano, nitro, hydroxy, SF5, OSChR' ¹ . ^{SO2NRb Rc} , N(Rd )(Re ), ^C (Q ^' ) ^{NRb Rc} . N(R ^b )C(Q ¹ )R ^a , C(O)R ^a , OC(O)R ^a or =Q ² ; or for Ci-C4-alkyl, C- _C4 -alkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, G-Cg-cycloalkyl. spirocyclically bound C2-Cg-cycloalkyl, spirocyclically bound heterocyclyl with 3 to 7 ring atoms, C-Cg-cycloalkylthio. C-Cg cycloalkoxy. Cß-Cg-cycloalkylsulphinyl or G-Cg-cycloalkylsulfonyl, all of which may be unsubstituted or substituted once to 5 times with halogen and/or optionally with 1 to 2 R ^g ; or phenyl or a 4- to 7-membered saturated, partially saturated or aromatic heterocycle from the group consisting of furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, iso - xazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2 ,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5 -triazinyl, oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, or dihydroisoxazolyl, all each unsubstituted or substituted with 1 to 2 R ^g

Q ¹ independently represents O, S, N0R ^a or NCN;

Q ² are independently O or N0R ^a ; and n is independently 0, 1 or 2.

More preferred (embodiment 3-1) are the compounds of formula (I) in which

A is N or CR ^A ; stands by

R ^A for H, halogen or Ci-C4-alkyl;

V is -C(Q ¹ )NR ^V1 R ^V2 ; stands by

steht, wobei diese Substituenten und P-01 bis P-04 alle jeweils unsubstituiert sein können, oder gegebenenfalls einfach bis funfach mit Halogen und/oder mit 1 bis 2 R^h substituiert sein können; R ^V1 for Ci-Cg-alkyl, G-CS-cycloalkyl or a saturated G-CS-Hctcrocyclyl from the series

stands, where these substituents and P-01 to P-04 can all be unsubstituted in each case, or can ^optionally be substituted once to five times with halogen and/or with 1 to 2 Rh;

R ^V2 for H; or for Ci-Cg-alkyl, Ci-Cg-alkoxy or Cß-Cv-cycloalkyl, all of which are unsubstituted or mono- to penta-substituted by halogen and/or optionally by 1 to 2 R ^g ; or

R ^V1 and R ^V2 together with the nitrogen atom to which they are attached represent a heterocycle from the series U-01 to U-06

U-01 and U-02 U-03 U-04 U-05 U-06 where all U-01 to U-06 can each be unsubstituted or optionally substituted once to 5 times with halogen and/or optionally with 1 to 2 ^rows

^R1 for H; stands for C 1 -C 4 -alkyl or C 2 -C 4 ^-alkenyl , all of which can be unsubstituted or substituted once to five times with halogen and/or optionally with 1 to 2 Rh;

R ² represents the substructure of the general formula -XYZ; stands by

X is phenyl or pyridyl, each unsubstituted or substituted by 1 to 3 R ^x ; stands by

R ^x independently of one another is halogen, cyano or C 1 -C 4 -alkyl, each unsubstituted or substituted by 1 to 2 R ^f ;

Y is -CR ^Y1 =N- where N is bonded to Z, or -NR ^Y2 -C(=Q ^Y )- where C is bonded to Z; each is included R ^Y1 and R ^Y2 for H; or for Ci-C2-alkyl in each case unsubstituted or substituted by 1 to 3 R ^Y11 ; each is included

R ^Y11 independently for halogen, cyano, Ci-C2-alkyl or C1-C2-alkoxy;

Q ^Y for O or S;

dabei ist # der Anknüpfungspunkt zu Y und dabei steht jedes Z for the fragments of the general formula (A1), (A2) or (A3);

where # is the connecting point to Y and where each stands

T for O or S;

R ^Z1 is phenyl substituted with 1 to 3 R ^Z11 ; each is included

R ^Z11 independently for halogen, cyano, OR ^a SR ^a , or for Ci-Cralkyl, C3-Cg-cycloalkyl, all unsubstituted or substituted by 1 to 3 R ^zla ; each is included

R ^zla for halogen, C iG alkoxy or C iG thioalkyl:

R ^Z2 , R ^Z2a and R ^Z3 are independently H; or for C1-C4-alkyl, in each case unsubstituted or substituted by 1 to 3 R ^Z21 ; each is included

R ^Z21 independently of one another are halogen or C iG-alkoxy: or

R ^Z2 and R ^Z3 together with the TCN moiety form a 5- to 6-membered ring; the R ^Z2 -R ^Z3 ring members consist of carbon atoms; 1 carbon atom ring member can consist of C(=O); this R ^Z2 -R ^Z3 unit is unsubstituted or substituted by 1 to 3 R ^Z21 ; each is included

R ^Z21 independently represent halogen, C' iG-alkyl. C1-C3 alkenyl, or C1-C3-

alkoxy; each is included R ^a is independently Ci-Cg-alkyl, Cs-Cg-cycloalkyl, C2-Cg-alkenyl or C2-Cg-alkynyl, all of which may be unsubstituted in each case, or 1 to 5 times by halogen and/or optionally by a R ^f may be substituted; or phenyl unsubstituted or substituted by 1 to 3 R ^g ;

R ^f is independently halogen, cyano, nitro, CAG, -cycloalkyl. Ci-C4 alkoxy, C1-C4 haloalkoxy, Ci-C4 alkylthio, Ci-C4 haloalkylthio, Ci-C4 alkylsulfmyl, Ci-C4 haloalkylsulfinyl, Ci-C4 alkylsulfonyl, Ci-C4 haloalkylsulfonyl, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl; or phenyl or a 5- or 6-membered heteroaromatic ring each unsubstituted or substituted with 1 to 3 R ^g ;

R ^g independently for halogen, cyano, nitro, Ci-C4-alkyl, GG-cycloalkyl. C1-C4 haloalkyl, Ci-C4 alkoxy, Ci-C4 haloalkoxy, Ci-C4 alkylthio, Ci-C4 haloalkylthio, C1-C4 alkylsulfmyl, Ci-C4 haloalkylsulfmyl, Ci-C4 alkylsulfonyl, Ci-C4-haloalkylsulfonyl, C1-C4-alkyl carbonyl or Ci-C4-alkoxycarbonyl;

R ^h independently for halogen, cyano, nitro, hydroxy, SF5, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfmyl, C1-C4-alkylsulfonyl, GG-cycloalkyl. spirocyclically bonded C2-Cg-cycloalkyl, spirocyclically bonded heterocyclyl with 3 to 7 ring atoms, C3-Cg-cycloalkylthio, GG-cycloalkoxy. GG-cycloalkylsilfmyl. GG-cycloalkylstilfonyl. each of which can be unsubstituted or substituted once to five times by halogen and/or optionally by 1 to 2 R ^g ; or phenyl or a 4- to 7-membered saturated, partially saturated or aromatic heterocycle from the group consisting of furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl , oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thi - adiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4 -Triazinyl, 1,3,5-triazinyl, oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, or dihydroisoxazolyl, each unsubstituted or substituted by 1 to 2 R ^g ;

Q ¹ for O; and n for 0, 1, or 2

Particularly preferred (embodiment 4-1) are the compounds of the formula (I) in which

A is N or CR ^A ; stands by

R ^A for H;

V is -C(O)NR ^V1 R ^V2 ; stands by R ^V1 for C'i-Cfi-alkyl. C -Ck-cycloalkyl or a saturated C -Ch-Hctcrocyclyl from the series of

P-01 P-04, where these substituents and P-01 and P-04 may all each be unsubstituted, or ^optionally substituted once to five times with halogen and/or with 1 to 2 Rh;

R ^V2 for H; or for Ci-Cg-alkyl, Ci-Cg-alkoxy or C3-C?-cycloalkyl, all of which are unsubstituted or mono- to penta-substituted by halogen and/or optionally by 1 to 2 R ^g ; or

R ^V1 and R ^V2 together with the nitrogen atom to which they are attached represent a heterocycle U-01;

U-01 where U-01 can in each case be unsubstituted or optionally substituted once to three times by halogen and/or optionally by 1 to 2 ^Rh ;

R ^{1 is} Ci-C4-alkyl, each of which may be unsubstituted or mono- to tri-substituted by halogen and/or optionally by 1 to 2 Rh;

R ² represents the substructure of the general formula -XYZ; stands by

X is phenyl unsubstituted or substituted with 1 to 3 R ^x ; stands by

R ^x are independently halogen, cyano or methyl

Y for - CR ^Y1 =N- where N is bonded to Z, or for

-NR ^Y2 -C(=Q ^Y )-, where C is bonded to Z; each is included

R ^Y1 and R ^Y2 for H; Q ^Y for O;

dabei ist # der Anknüpfüngspunkt zu Y und dabei steht jedes Z for the fragments of general formula (A1), (A2), (A3);

where # is the connecting point to Y and where each stands

T for S;

R ^Z1 is phenyl substituted with 1 to 3 R ^Z11 ; where 1 R ^Z11 is in 2-position and where each is standing

R ^{Z11 is} independently F, Cl, Br, CH3, CH2CH3, CH2CH2CH3, CH(CH3)2, cyclopropyl, _OCH3 , OCH2CH3, OCH2CH2CH3, OCH(CH3) ₂ , _CH2OCH3 or CH(CH3 _{) OCH3} ;

R ^Z2 , R ^Z2a and R ^Z3 independently represent H; or

R ^Z2 and R ^Z3 together with the TCN moiety form a 5- to 6-membered ring; the R ^Z2 -R ^Z3 ring members consist of carbon atoms; 1 carbon atom ring member can consist of C(=O); this R ^Z2 -R ^Z3 unit is unsubstituted or substituted by 1 to 2 R ^Z21 ; each is included

R ^{Z21 is} independently methyl; each is included

R ^g independently of one another is halogen, cyano, Ci-C4-alkyl, Cs-Cg-cycloalkyl, Ci-C4-haloalkyl, C1-C4-alkoxy or Ci-C4-haloalkoxy;

R ^h independently for halogen, cyano, nitro, hydroxy, C1-C4-alkyl, C1-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfmyl, Ci-C4-alkylsulfonyl, Cs-Cg-cycloalkyl, spirocyclic bonded C2-Cg-cycloalkyl, spirocyclic bonded heterocyclyl with 3 to 7 ring atoms, C -Cg- cycloalkylthio, C's-Cg-cycloalkoxy. Cs-Cg-cycloalkylsulphinyl or Cs-Cg-cycloalkylsulphonyl, all of which may be unsubstituted or substituted once to 5 times with halogen and/or optionally with 1 to 2 R ^g ; or phenyl or a 4- to 7-membered saturated, partially saturated or aromatic heterocycle from the group consisting of furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl , oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3- thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4- Triazinyl, 1,3,5-triazinyl, oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, or dihydroisoxazolyl, all each unsubstituted or substituted with 1 to 2 R ^g .

Emphasized (embodiment 5-1) are the compounds of formula (I) in which

A is N;

V is -C(O)NR ^V1 R ^V2 ; stands by

R ^V1 for trifluoromethylcyclohexyl, 3,3,3-trifluoropropyl, ao-propyl, cyclohexyl, 4,4,4-trifluorobutyl, 4,4-difluorocyclohexyl, para-trifluoromethoxybenzyl, para-trifluoromethylbenzyl, trifluoromethoxyethyl, tetrahydrothiopyran, ( 1-cyanocyclopropyl)methyl or 1,1,2,2-tetrafluorobutyl;

R ^{V2 is} H or methyl; or

R ^V1 and R ^V2 together with the nitrogen atom to which they are attached for

R ¹ is methyl;

R ² represents the substructure of the general formula -XYZ; stands by

X is phenyl unsubstituted or substituted by 1 R ^x ; stands by

R ^x is chloro, fluoro, cyano or methyl;

Y is -CH=N-, where N is bonded to Z; each is included

Z for the fragments of general formula (A2-1) or (A3-1);

(A2-1) (A3-1) where # is the connecting point to Y and each stands R ^Z1 is phenyl substituted with 1 to 2 R ^Z11 ; where 1 R ^Z11 is in 2-position and where each is standing

R ^Z11 independently represent methyl, methoxy or isopropyl.

A further preferred embodiment of the invention is represented by compounds of the formula (I) in which A is N and all the other structural elements in embodiment (1-1) or in embodiment (2-1) or in embodiment (3-1 ) or have the meanings given in embodiment (4-1).

A further preferred embodiment of the invention are compounds of the formula (I) in which R ^h independently represent halogen, cyano, nitro, hydroxy, SF5,OSC>2R ^a , SO2NR ^b R ^c , N(R ^d )(R ^e ), C(Q ¹ )NR ^b R ^c , N(R ^b )C(Q ¹ )R ^a , C(O)R ^a , OC(O)R ^a or =Q ² ; or for Ci-C ₄ -alkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -alkylthio, Ci-C ₄ -alkylsulfmyl, Ci-C ₄ -alkylsulfonyl, Cs-Cg-cycloalkyl, spirocyclically bonded C2-Cg-cycloalkyl , spirocyclic bonded heterocyclyl having 3 to 7 ring atoms, C's-Cg-cycloalkylthio. Cs-Cg-cycloalkoxy, Cs-Cg-cycloalkylsulphinyl or C's-Cg-cycloalkylsilfonyl. each of which can be unsubstituted or substituted once to 13 times by halogen and/or optionally by 1 to 2 R ^g and all other structural elements have the meanings given in embodiment (1-1).

A further preferred embodiment of the invention are compounds of the formula (I) in which R ^h independently represent halogen, cyano, nitro, hydroxy, SFs, OSCFR' ¹ . SO2NR ^b R ^c , N(R ^d )( ^Re ), C(Q ¹ )NR ^b R ^c , N(R ^b )C(Q ¹ )R ^a , C(O)R ^a , OC(O)R ^a or =Q ² ; or for Ci-C ₄ -alkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -alkylthio, Ci-C ₄ -alkylsulfmyl, Ci-C ₄ -alkylsulfonyl, G-Cg-cycloalkyl. spirocyclically bonded C2-Cg-cycloalkyl, spirocyclically bonded heterocyclyl having 3 to 7 ring atoms, -Cg-cycloalkylthio. Cs-Cg-cycloalkoxy, G-Cg-cycloalkylstilfinyl or G-Cg-cycloalkylstilfonyl. each of which can be unsubstituted or substituted once to 5 times by halogen and/or optionally by 1 to 2 R ^g and all other structural elements have the meanings given in embodiment (2-1).

A further preferred embodiment of the invention are compounds of the formula (I) in which R ^h independently represent halogen, cyano, nitro, hydroxy, SF5, Ci-C ₄ -alkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -Alkylthio, Ci-C ₄ -alkylsulfmyl, Ci-C ₄ -alkylsulfonyl, Cs-Cg-cycloalkyl, spirocyclically bonded C2-Cg-cycloalkyl, spirocyclically bonded heterocyclyl having 3 to 7 ring atoms, -Cg-cycloalkylthio. Cs-Cg-cycloalkoxy, C's-Cg-cycloalkylsilyl. C-Cg-cycloalkylsulfonyl. each of which can be unsubstituted or substituted one to five times by halogen and/or optionally by 1 to 2 R ^g and all other structural elements have the meanings given in embodiment (3-1). A further preferred embodiment of the invention are compounds of the formula (I) in which R ^h independently represent halogen, cyano, nitro, hydroxy, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci- C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, Cs-Cg-cycloalkyl, spirocyclically bonded C2-Cg-cycloalkyl, spirocyclically bonded heterocyclyl with 3 to 7 ring atoms, CACg-cycloalkylthio. C3-Cg-cycloalkoxy, Cs-Cg-cycloalkylsulphinyl or Cs-Cg-cycloalkylsulfonyl, all of which can be unsubstituted or mono- to 5-fold substituted with halogen and/or optionally with 1 to 2 R ^g and all other structural elements (4-1) have the meanings given.

A further preferred embodiment of the invention are compounds of the formula (I) in which R ^h is trifluoromethylcyclohexyl, 3,3,3-trifluoropropyl, isopropyl, cyclohexyl, 4,4,4-trifluorobutyl, 4,4- Difluorocyclohexyl, trifluoromethoxyethyl, tetrahydrothiopyran, (1-cyanocyclopropyl)methyl or 1,1,2,2-tetrafluorobutyl and all other structural elements (5-1) have the meanings given.

In a further preferred embodiment, the invention relates to compounds of the general formula (Ia) in which the structural elements V, R ¹ , R ^Y1 and R ^Z1 are in embodiment (1-1) or in embodiment (2-1) or in aspect (3-1) or have the meanings given in aspect (4-1) or the meanings given in aspect (5-1).

(I-a)

In a further preferred embodiment, the invention relates to compounds of the general formula (Ib) in which the structural elements V, R ¹ , R ^Y1 and R ^Z1 are in embodiment (1-1) or in embodiment (2-1) or in aspect (3-1) or have the meanings given in aspect (4-1) or the meanings given in aspect (5-1). (Ib)

In a further preferred embodiment, the invention relates to compounds of the general formula (Ic) in which the structural elements V, R ¹ , R ^Y1 and R ^Z1 are in embodiment (1-1) or in embodiment (2-1) or in Embodiment (3-1) or have the meanings given in embodiment (4-1) or in embodiment (5-1).

(I-c)

In a further preferred embodiment, the invention relates to compounds of the general formula (Id) in which the structural elements V, R ¹ , ^RY1 and R ^Z1 are in embodiment (1-1) or in embodiment (2-1) or in Embodiment (3-1) or have the meanings given in embodiment (4-1) or in embodiment (5-1).

(I-d)

Depending on the nature of the substituents, the compounds of the formula (I) can optionally also be present as stereoisomers, i.e. as geometric and/or optical isomers or isomer mixtures in different compositions. Both the pure stereoisomers and any mixtures of these isomers are the subject of this invention, even if in general only compounds of the formula (I) are mentioned here.

However, the optically active, stereoisomeric forms of the compounds of the formula (I) and their salts are preferably used according to the invention. The invention therefore relates both to the pure enantiomers and diastereomers and to mixtures thereof for controlling animal pests, which include arthropods and, in particular, insects.

The compounds of formula (I) can optionally exist in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are the subject of the invention and can be used according to the invention.

Unless otherwise defined elsewhere, the term "alkyl", either on its own or in combination with other terms such as haloalkyl, is understood in the context of the present invention to mean a radical of a saturated, aliphatic hydrocarbon group having 1 to 12 carbon atoms, which may be branched or unbranched. Examples of Ci-C 12 alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, see. -butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl n-heptyl, n-octyl, n- nonyl, n-decyl, n-undecyl and n-dodecyl. Of these alkyl radicals, Ci-Cg-alkyl radicals are particularly preferred. Ci-C4-alkyl radicals are particularly preferred.

Unless otherwise defined elsewhere, the term "alkenyl", either on its own or in combination with other terms, according to the invention is a linear or branched C2-Cn-alkenyl radical which has at least one double bond, for example vinyl, allyl, 1 -Propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1,3-pentadienyl, 1-hexenyl, 2 - hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and 1,4-hexadienyl. Of these, preference is given to C2-C9-alkenyl radicals and particular preference is given to C2-C4-alkenyl radicals.

Unless otherwise defined elsewhere, the term “alkynyl” refers to a linear or branched C2-Cn-alkynyl radical which has at least one triple bond, for example ethynyl, 1-propynyl, either on its own or in combination with other terms and propargyl, understood. Of these, preference is given to C-Cg-alkynylrcstc and particular preference is given to C3-C4-alkynyl radicals. The alkynyl radical can also have at least one double bond.

Unless otherwise defined elsewhere, the term “cycloalkyl”, either on its own or in combination with other terms, is understood according to the invention as meaning a C -CV cycloalkyl group, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Preferred of these are Cs-Cg-cycloalkylrcstc.

Unless otherwise defined elsewhere, the term “aryl” is understood according to the invention as meaning an aromatic radical having 6 to 14 carbon atoms, preferably phenyl, naphthyl, anthryl or phenanthrenyl, particularly preferably phenyl. Unless otherwise defined elsewhere, the term “arylalkyl” is understood to mean a combination of “aryl” and “alkyl” radicals defined according to the invention, with the radical generally being bonded via the alkyl group, examples of which are benzyl, phenylethyl or a- methylbenzyl, with benzyl being particularly preferred.

Unless otherwise defined elsewhere, “hetaryl” means a mono-, bi- or tricyclic heterocyclic group composed of carbon atoms and at least one heteroatom, where at least one cycle is aromatic. The hetaryl group preferably contains 3, 4, 5 or 6 carbon atoms selected from the group consisting of furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4- thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5- Triazinyl, Benzofiiranyl, Benzisofiiryl, Benzothienyl, Benzisothienyl, Indolyl, Isoindolyl, Indazolyl, Benzothiazolyl, Benzisothiazolyl, Benzoxazolyl, Benzisoxazolyl, Benzimidazolyl, 2,1,3-Benzoxadiazole, Quinolinyl, Isoquinolinyl, Cinnolinyl, Phthalazinyl, Quinazolinyl, Quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl and indolizinyl.

Unless otherwise defined elsewhere, “heterocyclyl” means a monocyclic, saturated or partially saturated 4-, 5-, 6- or 7-membered ring made up of C atoms and at least one heteroatom in the ring. The heterocyclyl group preferably contains 3, 4, 5 or 6 carbon atoms and 1 or 2 heteroatoms from the group consisting of oxygen, sulfur and nitrogen. Examples of heterocyclyl are azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, tetrahydrofuryl.

Unless otherwise defined elsewhere, “oxo-heterocyclyl” or “dioxo-heterocyclyl” means a heterocyclyl that contains a ring atom in at least one position in the ring, which has one or two (=0) - groups is substituted. A heteroatom such as, for example, sulfur is preferably substituted with one or two (=0) groups, which then results in the group -S(=O)- or -S(=O)2-, the S atom being a component of the ring is.

In the context of the present invention, radicals substituted by halogen, for example “haloalkyl”, are understood to mean radicals halogenated one or more times up to the maximum possible number of substituents. In the case of multiple halogenation, the halogen atoms can be the same or different. “Halogen” stands for fluorine, chlorine, bromine or iodine, preferably for fluorine or chlorine.

The term “alkoxy”, either on its own or in combination with other terms such as, for example, haloalkoxy, is understood here to mean an O-alkyl radical, the term “alkyl” having the meaning given above. General synthetic routes

A, J, T, V ¹ , V ² , X, ^RY1 , T and R ^Z1 have the meanings described above or in Scheme 1. The general formulas (Ia) and (Ib) thus correspond to the general formula (I), where R ² = XYZ, where Y is --CR ^Y1 =N-, Z is the fragment of the general formula (A3).

(Ib) For T = S For T = S

(la)

Scheme 1: General synthesis

Conditions: a) MciAI. toluene or THF, 40°C to 80°C; b) Pd(dppf)C12X CH2Cl2, CS2CO3, dioxane/H ₂ O, 90 °C; c) EtOH, reflux; d) EtOH, NaOAc, reflux;

In the first step of the sequence (Scheme 1), the methyl ester E-1 is converted to the corresponding amide. For this, the required amine is pre-stirred with MesAl at room temperature for between 5 and 30 minutes, then the ester is added and the mixture is heated to 40 to 100 °C for a period of between 4 and 16 h. Toluene, THF or dichloromethane are suitable as solvents. Such a prescription can be found, for example, in A. Basha, M. Lipton and SM Weinreb, Tetrahedron Lett., 1977, 18, 4171-4172. After working up and purification in a known manner, the intermediates E-2 can be converted to the intermediates E-3 by means of palladium catalysis. To do this, the required starting materials, E-2 and a boronic acid or pinacol ester, are dissolved in a solvent-water mixture, a base and the catalyst are added, and the entire reaction is stirred between 60 and 120 °C for 3 to 16 h under oxygen-free conditions . 1,4-Dioxane, THF, toluene are suitable as solvents, Pd(dppf)C12xCH2C12 or Pd(PPh3)4 are suitable as catalysts, Na2CC>3, K2CO3 or CS2CO3 are suitable as bases. The product is purified according to standard methods known to a person skilled in the art. In the next step, intermediate E-3 is converted to (1a). Such a reaction can be found, for example, in WO2013116053 or WO2013116052. Analogously, the starting material E-3 is dissolved in a solvent and E-4 is added and the mixture stirred at reflux. MeOH, EtOH or i-propanol are suitable as solvents, but EtOH is preferred. Compounds of the general formula (Ib) can then correspondingly from compounds of the general formula (Ia) with T = S and methyl bromoacetate, optionally in the presence of a base such as sodium acetate, in a suitable solvent such as ethanol, and at a suitable temperature, such as in a range from 50 °C to 80 °C. A representative specification of this method can be found in WO 2013116053 or WO 2013116052. Conditions preferred for each reaction are given under Scheme 1.

The building blocks E-1 required for the synthesis are either commercially available or can be prepared according to Scheme 2.

^{E'1b E} -1c

Scheme 2: Synthesis of the starting materials E-1

Conditions for A = N: a) K2CO3, DMF, R'-J (with J = Cl, Br, 1, OTf), 40 °C to 100 °C or toluene, NEts, H ₂ C=CHR ¹ , 40 ° C to 100°C; b) K2CO3, DMF, RM (with J = Cl, Br, 1, OTf), RT to 100 °C; c) Pd(dppf)Cl ₂ x acetone, NaOAc, MeOH, 1 to 10 bar CO, 40 °C to 100 °C.

Either the NH-triazole El a can be alkylated directly or the symmetrical NH-triazole El-b is first alkylated and then converted to the methyl ester El by means of a Pd-catalyzed carbonylation. For the first route, the starting material is stirred with a base, for example Na ₂ CO3, K2CO3 or CS2CO3 in DMF at temperatures between 40°C and 100°C and then isolated using standard methods known to a person skilled in the art. Alternatively, the radical R ¹ can be introduced via a Michael addition, for which the starting material El a is dissolved in a suitable solvent such as toluene, acetonitrile or DMF and a suitable base such as triethylamine or N,N-diisopropylethylamine at temperatures between 40° C. and 80 ° C is stirred with the appropriate electrophile. The processing and product isolation are carried out according to standard methods. Alternatively, the symmetrical NH-triazole El-b can be converted under conditions analogous to a) to give the intermediate E-lc. This is then converted to the desired starting material El. For this purpose El-c is dissolved in methanol, sodium acetate and a suitable catalyst are added. For example, Pd(dppf)Cl ₂ or Pd(OAc) ₂ with ligands such as PPI13 or dppe are suitable here. the The mixture is then stirred at temperatures between 40° C. and 100° C. under a carbon monoxide pressure of 1 to 10 bar. After filtration and product isolation, the starting materials E1 can be represented in this way.

isomers

Depending on the nature of the substituents, the compounds of the formula (I) can be present as geometric and/or as optically active isomers or corresponding isomer mixtures in various compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The invention thus encompasses both pure stereoisomers and any mixtures of these isomers.

Procedures and Uses

The invention also relates to methods for controlling animal pests, in which the compounds of formula (I) are allowed to act on animal pests and/or their habitat. Preference is given to combating animal pests in agriculture and forestry and in the protection of materials. This preferably excludes methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods which are carried out on the human or animal body.

The invention also relates to the use of the compounds of the formula (I) as pesticides, in particular crop protection agents.

In the context of the present application, the term pesticide always also includes the term plant protection agent.

With good plant tolerance, favorable warm-blooded toxicity and good environmental compatibility, the compounds of the formula (I) are suitable for protecting plants and plant organs from biotic and abiotic stress factors, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, Arachnids, helminths and molluscs found in agriculture, horticulture, animal husbandry, aquaculture, forests, gardens and leisure facilities, in the protection of stored products and materials and in the hygiene sector.

In the context of the present patent application, the term "hygiene" is to be understood as meaning any and all measures, regulations and procedures which aim to prevent diseases, in particular infectious diseases, and which serve to protect human health and animals and/or protect the environment and/or maintain cleanliness. According to the invention, this includes in particular measures for cleaning, disinfecting and sterilizing, for example, textiles or hard surfaces, in particular surfaces made of glass, wood, cement, porcelain, ceramics, plastic or metal(s) to ensure that they are free of Hygiene pests and/or their excrements. Preferably excluded from the scope of the invention in this respect are surgical or therapeutic regimens of treatment to be applied to the human or animal bodies and diagnostic regimens to be performed on the human or animal bodies.

The term "hygiene sector" thus covers all areas, technical fields and industrial applications where these hygiene measures, regulations and procedures are important, for example with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels , hospitals, stables, animal husbandry, etc.

The term "sanitary pest" should therefore be understood to mean one or more animal pests whose presence in the sanitary sector is problematic, particularly for health reasons. It is therefore a major objective to avoid or minimize the presence and/or exposure to hygiene pests in the hygiene sector. In particular, this can be achieved by using a pesticide that can be used both to prevent an infestation and to manage an infestation that is already present. One can also use preparations that prevent or reduce exposure to pests. Sanitary pests include, for example, the organisms mentioned below.

The term "hygiene protection" thus covers all actions with which these hygiene measures, regulations and procedures are maintained and/or improved.

The compounds of the formula (I) can preferably be used as pesticides. They are active against normally sensitive and resistant species and against all or some developmental stages. The pests mentioned above include:

Pests from the phylum Arthropoda, in particular from the class Arachnida z. B. Acarus spp., e.g. B. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., e.g. Aculus fockeui, Aculus Schlechtedali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., e.g. B. Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., e.g. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., e.g. B. Eutetranychus banksi, Eriophyes spp., e.g. B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., e.g. B. Hemitarsonemus latus (= Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., e.g. Oligonychus coffeae, Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Omithodorus spp., Omithonyssus spp., Panonychus spp., e.g. B. Panonychus citri (=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., e.g. B. Tarsonemus confusus, Tarsonemus pallidas, Tetranychus spp., e.g. B. Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; from the class of the Chilopoda z. B. Geophilus spp., Scutigera spp.; from the order or class of the Collembola z. B. Onychiurus armatus; Sminthurus viridis; from the class of Diplopoda z. B. Blaniulus guttulatus; from the class of the Insecta, e.g. B. from the order of Blattodea z. B. Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., e.g. B. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of the Coleoptera z. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agrilus spp., e.g. B. Agrilus planipennis, Agrilus coxalis, Agrilus bilineatus, Agrilus anxius, Agriotes spp., e.g. Agriotes linneatus, Agriotes mancus, Agriotes obscurus Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anomala dubia, Anoplophora spp., e.g. B. Anoplophora glabripennis, Anthonomus spp., e.g. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Athous haemorrhoidales, Atomaria spp., e.g. B. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., e.g. B. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., e.g. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., e.g. B. Chaetocnema confmis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., e.g. B. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., e.g. B. Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dendroctonus spp., e.g. B. Dendroctonus ponderosae, Dermestes spp., Diabrotica spp., e.g. B. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., e.g . B. Epilachna borealis, Epilachna varivestis, Epitrix spp., e.g. B. Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus comutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hoplia argentea, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., e.g. B. Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnostema consanguinea, Lasioderma serricome, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., e.g. B. Leucoptera coffeella, Limonius ectypus, Lissorhoptrus oryzophilus, Listronotus (=Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp., e.g. B. Megacyllene robiniae, Megascelis spp., Melanotus spp., e.g. B. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., e.g. B. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., e.g. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., e.g. Oulema melanopus, Oulema oryzae, Oxycetoniajucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga Helleri, Phyllotreta spp., e.g. B. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., e.g. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum, Scolytus spp., e.g. B. Scolytus multistriatus, Sinoxylon perforans, Sitophilus spp., e.g. B. Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Stemechus spp., e.g. B. Stemechus paludatus, Symphyletes spp., Tanymecus spp., e.g. B. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., e.g. B. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., e.g. B. Zabrus tenebrioides; from the order of the Dermaptera z. B. Anisolabis maritime, Forficula auricularia, Labidura riparia; from the order of the Diptera z. B. Aedes spp., e.g. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., e.g. B. Agromyza frontella, Agromyza parvicomis, Anastrepha spp., Anopheles spp., e.g. B. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., e.g. B. Bactrocera Cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp., e.g. B. Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., z. Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., e.g. B. Dasineura brassicae, Delia spp., e.g. B. Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., e.g. B. Drosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., e.g. B. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., e.g. B. Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musea spp., e.g. B. Musea domestica, Musea domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterbomiella subcincta, Pegomya or Pegomyia spp., e.g. B. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., e.g. Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., e.g. B. Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., e.g. B. Tipula paludosa, Tipula simplex, Toxotrypana curvicauda; from the order of the Hemiptera z. B. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., e.g. B. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., e.g. B. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., e.g. B. Aonidiella aurantii, Aonidiella citrina, Aonidiella inomata, Aphanostigma piri, Aphis spp., e.g. B. Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis vibumiphila, Arboridia apicalis , Arytainilla spp., Aspidiella spp., Aspidiotus spp., e.g. B. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., e.g. B. Cacopsylla pyricola, Calligypona marginata, Capulinia spp., Cameocephala fiilgida, Ceratovacuna lanigera, Cercopidae, Ceropiastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita o-nukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus - cadulina mbila, Coccomytilus semi, Coccus spp., e.g. B. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes chittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., e.g. B. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., e.g. B. Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., e.g. B. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., e.g. B. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striate Uns, Lecanium spp., e.g. B. Lecanium comi (=Parthenolecanium comi), Lepidosaphes spp., e.g. B. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., e.g. B. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., e.g. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus omatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., e.g. Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., e.g. B. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., e.g. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., e.g. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., e.g. B. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Pianococcus spp., e.g. B. Pianococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., e.g. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus vibumi, Psyllopsis spp., Psylla spp., e.g. B. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., e.g. B. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., e.g. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., e.g. B. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetiaoleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella fiircifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayphela, Tetragonppoce ., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., e.g. B. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., e.g. B. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.; from the suborder of theHeteropteraz. B. Aelia spp., Anasatristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., e.g. B. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops fiircatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., e.g. B. Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicomis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygococoris spp., e.g. B. Lygocoris pabulinus, Lygus spp., e.g. B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monalonion atratum, Nezara spp., e.g. B. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., e.g. B. Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.; from the order of the Hymenoptera z. B. Acromyrmex spp., Athalia spp., e.g. B. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., e.g. B. Diprion similis, Hoplocampa spp., e.g. B. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., e.g. B. Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., e.g. B. Vespa crabro, Wasmannia auropunctata, Xeris spp.; from the order of the Isopoda z. B. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of the Isoptera z. B. Coptotermes spp., e.g. B. Coptotermes formosanus, Comitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermes spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., e.g. B. Reticulitermes flavipes, Reticulitermes hesperus; from the order of the Lepidoptera z. B. Achroia grisella, Acronicta major, Adoxophyes spp., e.g. B. Adoxophyes orana, Aedia leucomelas, Agrotis spp., e.g. B. Agrotis segetum, Agrotis ipsilon, Alabama spp., e.g. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., e.g. B. Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., e.g. Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., e.g. B. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., e.g. B. Dioryctria zimmermani, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., e.g. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., e.g. B. Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., e.g. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., e.g. B. Helicoverpa armigera, Helicoverpa zea, Heliothis spp., e.g. B. Heliothis virescens, Hepialus spp., e.g. B. Hepialus humuli, Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., e.g. B. Leucoptera coffeella, Lithocolletis spp., e.g. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., e.g. B. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., e.g. B. Lymantria dispar, Lyonetia spp., e.g. B. Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp ., Orthaga spp., Ostrinia spp., e.g. B. Ostrinia nubilalis, Panolis flammea, Pamara spp., Pectinophora spp., e.g. B. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., e.g. B. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., e.g. B. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., e.g. B. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (=Plutella maculipennis), Podesia spp., z. B. Podesia syringae, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., e.g. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., e.g. B. Schoenobius bipunctifer, Scirpophaga spp., e.g. B. Scirpophaga innotata, Scotia segetum, Sesamia spp., e.g. B. Sesamia inferens, Sparganothis spp., Spodoptera spp., e.g. B. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., e.g. B. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp.; from the order of the Orthoptera or Saltatoria z. B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., e.g. B. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., e.g. B. Locusta migratoria, Melanoplus spp., e.g. B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order of the Phthiraptera z. B. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp.; from the order of the Psocoptera z. B. Lepinotus spp., Liposcelis spp.; from the order of the Siphonaptera z. B. Ceratophyllus spp., Ctenocephalides spp., e.g. B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of the Thysanoptera z. B. Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., e.g. B. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Thrips cardamomi, Taeniothrips spp spp., e.g. B. Thrips palmi, Thrips tabaci; from the order of the Zygentoma (= Thysanura), z. B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla z. B. Scutigerella spp., e.g. B. Scutigerella immaculata;

Pests from the Mollusca tribe, e.g. B. from the class of Bivalvia, z. B. Dreissena spp.; and from the class of Gastropoda z. B. Arion spp., e.g. B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., e.g. B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.;

The compounds of the formula (I) can optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant traits, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including agents against viroids) or used as an anti-MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism) agent. If appropriate, they can also be used as intermediates or precursors for the synthesis of other active substances.

Formulations/Application forms

The present invention further relates to formulations, in particular formulations for controlling unwanted animal pests. The formulation can be applied to the animal pest and/or its habitat.

The formulation according to the invention can be provided to the end user as a ready-to-use “application form”, ie the formulations can be applied directly to the plants or seeds using a suitable device such as a spray or dust device. Alternatively, the formulations may be provided to the end user in the form of concentrates to be diluted, preferably with water, prior to use. Thus, unless otherwise specified, the term "formulation" refers to such a concentrate, while the term "use form" refers to a solution ready for use by the end user, ie usually such a diluted formulation. The formulation according to the invention may be prepared in a conventional manner, for example by mixing the compound of the invention with one or more suitable excipients such as those disclosed herein.

The formulation comprises at least one compound of the invention and at least one agriculturally useful adjuvant, e.g., carrier and/or surfactant(s).

A carrier is a solid or liquid, natural or synthetic, organic or inorganic substance that is generally inert. The carrier generally improves the application of the compounds, for example to plants, plant parts or seeds. Examples of suitable solid supports include, but are not limited to, ammonium salts, especially ammonium sulfates, ammonium phosphates and ammonium nitrates, ground natural rocks such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, silica gel, and ground synthetic rocks, such as finely divided silica, alumina and silicates. Examples of typical suitable solid carriers for preparing granules include, but are not limited to, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, synthetic granules of inorganic and organic flours, and granules of organic materials such as paper, sawdust, coconut shells , corn on the cob and tobacco stalks. Examples of suitable liquid carriers include, but are not limited to, water, organic solvents, and combinations thereof. Examples of suitable solvents include polar and non-polar organic chemical liquids, for example from the classes of aromatic and non-aromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene, tetrahydronaphthalene, alkylnaphthalene, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethyl - ene or methylene chloride), alcohols and polyols (which can also be substituted, etherified and/or esterified, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol or glycol), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone or cyclohexanone), Esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides (such as dimethylformamide or fatty acid amides) and esters thereof, lactams (such as N-alkylpyrrolidones, especially N-methylpyrrolidone) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide ), oils of vegetable or animal origin, nit nitriles (alkyl nitriles such as acetonitrile, propiononitrile, butyronitrile, or aromatic nitriles such as benzonitrile), carbonic esters (cyclic carbonic esters such as ethylene carbonate, propylene carbonate, butylene carbonate, or dialkyl carboxylic esters such as dimethyl carbonate, diethyl carbonate, dipropyl carbonate, dibutyl carbonate, dioctyl carbonate). The carrier can also be a liquified gaseous diluent, i.e. a liquid which is gaseous at normal temperature and pressure, for example aerosol propellants such as halocarbons, butane, propane, nitrogen and carbon dioxide.

Preferred solid supports are selected from clays, talc and silica. Preferred liquid carriers are selected from water, fatty acid amides and esters thereof, aromatic and non-aromatic hydrocarbons, lactams, lactones, carbonic acid esters, ketones, (poly)ethers.

The amount of carrier typically ranges from 1% to 99.99% by weight, preferably from 5% to 99.9% by weight, more preferably from 10% to 99.5% by weight and most preferably from 20% to 99% by weight. -% of formulation.

Liquid carriers are typically present in the range 20% to 90%, for example 30% to 80% by weight of the formulation.

Solid carriers are typically present in the range 0% to 50%, preferably 5% to 45%, for example 10% to 30% by weight of the formulation.

When the formulation includes two or more carriers, the outlined ranges refer to the total amount of carrier.

The surfactant can be ionic (cationic or anionic), amphoteric or nonionic such as ionic or nonionic emulsifiers, foaming agents, dispersing agents, wetting agents, penetrants and any mixtures thereof. Examples of suitable surfactants include, without limitation, salts of polyacrylic acid, ethoxylated poly(alpha-substituted)acrylate derivatives, salts of lignosulfonic acid (such as sodium lignosulfonate), salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide and/or propylene oxide with or without alcohols, fatty acids or fatty amines (for example polyoxyethylene fatty acid esters such as castor oil ethoxylate, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of Polyols (such as fatty acid esters of glycerol, sorbitol or sucrose), sulfates (such as alkyl sulfates and alkyl ether sulfates), sulfonates (for example alkyl sulfonates, aryl sulfonates and alkyl benzene sulfonates), sulfonated polymers of naphthalene/formaldehyde , phosphate esters, protein hydrolysates, lignosulfite waste liquors and methylcellulose. Where reference is made to salts in this paragraph, this preferably refers to the relevant alkali metal, alkaline earth metal and ammonium salts.

Preferred surfactants are selected from ethoxylated poly(alpha-substituted)acrylate derivatives, polycondensates of ethylene oxide and/or propylene oxide with alcohols, polyoxyethylene fatty acid esters, alkylbenzene sulfonates, sulfonated polymers of naphthalene/formaldehyde, polyoxyethylene fatty acid esters such as castor oil ethoxylate, sodium lignosulfonate and arylphenol ethoxylate.

The amount of surfactant is typically in the range 5 to 40%, for example 10 to 20% by weight of the formulation. Further examples of suitable excipients include water-repellent substances, drying agents, binders (adhesives, adhesives, fixing agents such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids such as cephalins and lecithins and synthetic phospholipids, polyvinylpyrrolidone and tylose), thickeners and secondary thickeners (such as cellulose ethers, acrylic acid derivatives, xanthan gum, modified clays e.g. those available under the name Bentone, and finely divided silica), stabilizers (e.g. cold stabilizers, preservatives (e.g. dichlorophone, benzyl alcohol hemiformal, l, 2-benzisothiazolin-3-one, 2-methyl -4-isothiazolin-3-one), antioxidants, light stabilizers, especially UV stabilizers, and other agents that improve chemical and/or physical stability), dyes or pigments (e.g inorganic cal pigments such as iron oxide, titanium oxide and Prussian blue; organic dyes e.g. alizarin, azo and metal phthalocyanine dyes), antifoams (e.g. silicone antifoams and magnesium stearate), antifreeze, adhesives, gibberellins and processing aids, mineral and vegetable oils, fragrances, waxes, nutrients (including trace nutrients such as salts of iron, manganese , boron, copper, cobalt, molybdenum and zinc), protective colloids, thixotropic substances, penetrants, sequestrants and complexing agents.

The selection of excipients depends on the intended use of the compound according to the invention and/or on the physical properties of the compound(s). Furthermore, auxiliaries can be selected in such a way that they impart certain properties (technical, physical and/or biological properties) to the formulations or the use forms produced from them. Through the choice of excipients, it may be possible to tailor the formulations to specific needs.

The formulation comprises an insecticidally/acaricidally/nematicidally effective amount of the compound(s) of the invention. The term "effective amount" means an amount sufficient to control insect/mite pests on cultivated plants or for the protection of materials and which does not cause significant damage to the plants treated. Such an amount can vary within a wide range and depends on various factors such as the insect/mite species to be controlled, the cultivated plant or material treated, the climatic conditions and the particular compound according to the invention used. The formulation according to the invention usually contains 0.01 to 99% by weight, preferably 0.05 to 98% by weight, particularly preferably 0.1 to 95% by weight, even more preferably 0.5 to 90% by weight , most preferably 1 to 80% by weight of the compound of the invention. It is possible that a formulation comprises two or more compounds according to the invention. In such case, the outlined ranges refer to the total amount of the compounds of the present invention.

The formulation of the present invention may be in any conventional type of formulation such as solutions (e.g. aqueous solutions), emulsions, water and oil based suspensions, Powders (e.g. wettable powders, soluble powders), dusts, pastes, granules (e.g. soluble granules, scattered granules), suspoemulsion concentrates, natural or synthetic products impregnated with the compound according to the invention, fertilizers and also microencapsulations in polymeric substances. The compound of the invention may be in a suspended, emulsified or dissolved form. Examples of certain suitable formulation types are solutions, water-soluble concentrates (e.g. SL, LS), dispersion concentrates (DC), suspensions and suspension concentrates (e.g. SC, OD, OF, FS), emulsion concentrates (e.g. EC), emulsions (e.g. EW, EO, ES , ME, SE), capsules (e.g. CS, ZC), pastes, lozenges, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressed parts (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 treating plant propagation material such as seeds (e.g. GW, GF). These and other formulation types are defined by the Food and Agriculture Organization of the United Nations (FAO). For an overview, see "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th ed. May 2008, Croplife International.

The formulation according to the invention is preferably in the form of one of the following types: EC, SC, FS, SE, OD, WG, WP, CS, particularly preferably EC, SC, OD, WG, CS.

Further details on examples of formulation types and their preparation are given below. When two or more compounds of the present invention are present, the outlined amount of compound of the present invention refers to the total amount of the compounds of the present invention. Conversely, this also applies to all other components of the formulation if two or more representatives of such a component, e.g. a wetting agent or binder, are present. i) Water-soluble concentrates (SL, LS)

10-60% by weight of at least one compound according to the invention and 5-15% by weight of surfactant (e.g. polycondensates of ethylene oxide and/or propylene oxide with alcohols) are dissolved in such an amount of water and/or water-soluble solvents (e.g. alcohols such as propylene glycol and carbonates such as propylene carbonate) dissolved so that the total amount is 100% by weight. Before use, the concentrate is diluted with water. ii) dispersion concentrates (DC)

5-25 wt. % of at least one compound according to the invention and 1-10 wt. % results. Diluting with water gives a dispersion. iii) Emulsifiable Concentrates (EC) 15-70% by weight of at least one compound of the invention and 5-10% by weight of surfactant (e.g. a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in such amount of water-insoluble organic solvent (e.g. aromatic hydrocarbon or fatty acid amide) and, if necessary, additional water-soluble solvent, so that the total amount is 100% by weight. An emulsion is obtained by diluting with water. iv) Emulsions (EW, EO, ES)

5-40 wt. % of at least one compound according to the invention and 1-10 wt. % water-insoluble organic solvent (e.g. aromatic hydrocarbon) dissolved. The mixture is added to water by an emulsifying machine in such an amount that the total amount becomes 100% by weight. The formulation obtained is a homogeneous emulsion. Before use, the emulsion can be further diluted with water. v) Suspensions and suspension concentrates v-1) Water-based (SC, FS)

In a suitable grinder, e.g. B. a ball mill, 20-60 wt .-% of at least one inventive compound with the addition of 2-10 wt .-% surfactant (e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2 wt .-% thickener (e.g. xanthan gum ) and water to a fine active ingredient suspension. The water is added in such an amount that the total amount is 100% by weight. A stable suspension of the active substance is obtained by dilution with water. For FS-type formulations, up to 40% by weight of binder (e.g. polyvinyl alcohol) is added. v-2) Oil Based (OD, OF)

In a suitable grinding device, for example a ball mill, 20-60% by weight of at least one compound according to the invention are ground with the addition of 2-10% by weight of surfactant (for example sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2% by weight. Thickeners (e.g. modified clay, in particular Bentone, or silicon dioxide) and an organic vehicle are crushed into a fine suspension of active ingredient and oil. The organic carrier is added in such an amount that the total amount is 100% by weight. A stable dispersion of the active substance is obtained by dilution with water. vi) Water dispersible granules and water soluble granules (WG, SG)

1-90 wt. %, preferably 20-80 wt. %, most preferably 50-80 wt ground and using typical technical applications such as extrusion, spray drying, fluidized bed granulation converted into water-dispersible or water-soluble granules. Surfactant and carrier material are used in such an amount that a total amount of 100% by weight is obtained. A stable dispersion or solution of the active ingredient is obtained by diluting with water. vii) Water dispersible powders and water soluble powders (WP, SP, WS)

50-80 wt a total of 100% by weight is ground. A stable dispersion or solution of the active ingredient is obtained by diluting with water. viii) Gel (GW, GP)

In a ball mill, 5-25% by weight of at least one compound according to the invention are mixed with the addition of 3-10% by weight of surfactant (e.g. sodium lignosulfonate), 1-5% by weight of binder (e.g. carboxymethylcellulose) and an amount of water that you come to a total of 100 wt .-% crushed. This gives a fine suspension of the active substance. A stable suspension of the active substance is obtained by dilution with water. ix) microemulsion (ME)

5-20% by weight of at least one compound according to the invention are added to 5-30% by weight organic solvent mixture (e.g. fatty acid dimethylamide and cyclohexanone), 10-25% by weight surfactant mixture (e.g. polyoxyethylene fatty alcohol ether and arylphenol ethoxylate) and such an amount of water that you come to a total amount of 100 wt .-%, given. This mixture is stirred for 1 hour, whereby a thermodynamically stable microemulsion forms spontaneously. x) Microcapsules (CS)

An oil phase with 5-50% by weight of at least one compound according to the invention, 0-40% by weight of water-insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15% by weight of acrylic monomers (e.g. methyl methacrylate, methacrylic acid and a di - or triacrylate) are dispersed in an aqueous solution of a protective colloid (eg polyvinyl alcohol). A free-radical polymerization initiated with a free-radical initiator leads to the formation of poly(methy)acrylate microcapsules. Alternatively, an oil phase comprising 5-50% by weight of at least one compound of the invention, 0-40% by weight of water-insoluble organic solvent (e.g. aromatic hydrocarbon) and an isocyanate monomer (e.g. diphenylmethene-4,4'-diisocyanate) is dissolved in an aqueous Dispersed solution of a protective colloid (eg polyvinyl alcohol), this leads to the formation of polyurea microcapsules. If necessary, you can also add a polyamine (e.g. hexamethylenediamine) apply to induce the formation of polyurea microcapsules. The monomers make up 1-10% by weight of the total CS formulation. xi) dust powder (DP, DS)

1-10% by weight of at least one compound according to the invention are finely ground and intimately mixed with such an amount of solid carrier, e.g. finely divided kaolin, that the total amount is 100% by weight. xii) Granules (GR, FG)

0.5-30% by weight of at least one compound according to the invention is finely ground and associated with such an amount of solid support (e.g. silicate) that the total amount is 100% by weight. xiii) Ultra Low Volume Liquids (UL)

1-50% by weight of at least one compound according to the invention are dissolved in such an amount of organic solvent, e.g. aromatic hydrocarbon, that the total amount is 100% by weight.

Formulation types i) to xiii) can contain further auxiliaries such as 0.1-1% by weight of preservatives, 0.1-1% by weight of antifoams, 0.1-1% by weight of dyes and/or pigments and 5- 10% by weight of antifreeze.

mixtures

The compounds of formula (I) can also be used in a mixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficial insects, herbicides, fertilizers, bird repellents, phytotonics, sterilants, safeners, semiochemicals and/or plant growth regulators become, e.g. B. to broaden the spectrum of action, to extend the duration of action, to increase the speed of action, to prevent repellency or to prevent the development of resistance. Furthermore, such combinations of active ingredients can increase plant growth and/or tolerance to abiotic factors such as e.g. B. high or low temperatures, against drought or against increased water or soil salt content. It is also possible to improve flowering and fruiting behavior, optimize germination and rooting, facilitate harvesting and increase crop yield, influence ripeness, increase the quality and/or nutritional value of the harvested products, extend the shelf life and/or improve the workability of the harvested products.

Furthermore, the compounds of formula (I) in a mixture with other active ingredients or semiochemicals, such as attractants and / or bird repellents and / or plant activators and / or Growth regulators and/or fertilizers are present. Likewise, the compounds of the formula (I) can be used to improve the plant traits such as, for example, growth, yield and quality of the crop.

In a particular embodiment of the invention, the compounds of the formula (I) are present in formulations or in the use forms prepared from these formulations as a mixture with other compounds, preferably those as described below.

If one of the compounds mentioned below can occur in different tautomeric forms, these forms are also included, even if they were not explicitly mentioned in each case. If they are capable of doing so because of their functional groups, all of the mixing partners mentioned can also form salts with suitable bases or acids.

Insecticides/Acaricides/Nematicides

The active ingredients mentioned here by their "Common Name" are known and are described, for example, in the pesticide manual ("The Pesticide Manual" 16th Ed., British Crop Protection Council 2012) or can be researched on the Internet (e.g. http://www.alanwood. net/pesticides). The classification is based on the IRAC Mode of Action Classification Scheme in effect at the time of filing this patent application.

(1) Acetylcholinesterase (AChE) Inhibitors, preferably carbamates selected from Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, O- xamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb, or organophosphates selected from acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, Demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl-O-(methoxyaminothio -phosphoryl)salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxy demeton -methyl, parathion-methyl, Ph enthoate, phorate, phosalon, phosmet, phosphamidone, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.

(2) GAB A-controlled chloride channel blockers, preferably cyclodiene-organochlorines selected from chlordane and endosulfan, or phenylpyrazoles (fiprole) selected from ethiprole and fipronil.

(3) Sodium channel modulators, preferably pyrethroids selected from acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin , beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- Cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR)-trans-isomer], deltamethrin, empenthrin [(EZ)-(lR)-isomer], esfenvalerate, E- tofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(1R)-trans-isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin and transfluthrin, or DDT or methoxychlor.

(4) Competitive modulators of the nicotinic acetylcholine receptor (nAChR), preferably neonicotinoids selected from acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam, or nicotine, or sulfoximine selected from sulfoxaflor, or butenolide selected from flupyradifuron , or mesoionics selected from triflumezopyrim.

(5) Allosteric modulators of the nicotinic acetylcholine receptor (nAChR), preferably spinosyns selected from spinetoram and spinosad.

(6) Allosteric modulators of the glutamate-dependent chloride channel (GluCl), preferably avermectins/milbemycins selected from abamectin, emamectin benzoate, lepimectin and milbemectin.

(7) Juvenile hormone mimetics, preferably juvenile hormone analogues selected from hydroprene, kinoprene and methoprene, or fenoxycarb or pyriproxyfen.

(8) Various non-specific (multi-site) inhibitors, preferably alkyl halides selected from methyl bromide and other alkyl halides, or chloropicrin, or sulfuryl fluoride, or borax, or tartar emetic, or methyl isocyanate generators selected from diazomet and metam.

(9) TRPV channel modulators of chordotonal organs, preferably pyridinazomethanes selected from pymetrozine and pyrifluquinazone or pyropenes selected from afidopyropene.

(10) CHS1-related mite growth inhibitors selected from clofentezine, hexythiazox, diflovidazine and etoxazole.

(11) Insect intestinal membrane microbial disruptors selected from Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenehrionis and B./. plant proteins selected from CrylAb, CrylAc, CrylFa, Cry 1A. 105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb and Cry34Abl/35Abl.

(12) Inhibitors of mitochondrial ATP synthase, preferably ATP disruptors selected from diafenthiuron, or organotin compounds selected from azocyclotin, cyhexatin and fenbutatin oxide, or propargite or tetradifon. (13) Oxidative phosphorylation decouplers by perturbation of the proton gradient selected from chlorfenapyr, DNOC and sulfluramide.

(14) Blockers of the nicotinic acetylcholine receptor channel selected from Bensultap, Cartap hydrochloride, Thiocyclam and Thiosultap sodium.

(15) CHS1-related chitin biosynthesis inhibitors, preferably benzoylureas, selected from bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

(16) Inhibitors of chitin biosynthesis type 1 selected from buprofezin.

(17) Moult disruptor (particularly in Diptera, i.e., fly flies) selected from cyromazine.

(18) Ecdysone receptor agonists, preferably diacylhydrazines, selected from chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

(19) Octopamine receptor agonists selected from amitraz.

(20) Mitochondrial complex III electron transport inhibitors selected from hydramethylnon, acequinocyl, fluacrypyrim and bifenazate.

(21) Mitochondrial complex I electron transport inhibitors, preferably METI acaricides and insecticides selected from fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad, or rotenone (Derris).

(22) Blockers of the voltage-gated sodium channel, preferably oxadiazines selected from indoxacarb or semicarbazones selected from metaflumizone.

(23) Inhibitors of acetyl-CoA carboxylase, preferably tetronic and tetramic acid derivatives selected from spirodiclofen, spiromesifen, spiropidione and spirotetramat.

(24) Inhibitors of mitochondrial complex IV electron transport, preferably phosphides selected from aluminum phosphide, calcium phosphide, phosphine and zinc phosphide, or cyanides selected from calcium cyanide, potassium cyanide and sodium cyanide.

(25) Inhibitors of mitochondrial complex II electron transport, preferably beta-ketonitrile derivatives selected from cyenopyrafen and cyflumetofen, or carboxanilides selected from pyflubumid.

(28) Ryanodine receptor modulators, preferably diamides selected from chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide and tetraniliprole.

(29) Modulators of chordotonal organs (with undefined target structure) selected from flonicamid. (30) Allosteric modulators of the GABA -dependent chloride channel, preferably meta-diamides selected from broflanilide or isoxazoles selected from fluxametamide.

(31) Baculoviruses, preferably granuloviruses (GVs) selected from Cydia pomonella GV and Thaumatotibia leucotreta (GV) or nucleopolyhedroviruses (NPVs) selected from Anticar sia gemmatalis MNPV and Helicoverpa armigera NPV.

(32) Allosteric modulators (site II) of the nicotinic acetylcholine receptor selected from GS-omega/kappa-HXTX-Hv 1 a peptide.

(33) Other active ingredients selected from acynonapyr, afoxolaner, azadirachtin, benclothiaz, benzoximate, benzpyrimoxane, bromopropylate, quinomethionate, chloroballethrin, cryolite, cyclobutrifluram, cycloxaprid, cyetpyrafen, cyhalodiamide, cyproflanilide (CAS 2375110-88-4), dicloromezotiaz, dico - fol, dimpropyridaz, epsilon-metofluthrin, epsilon-momfluthrin, flometoquine, fluazaindolizine, flucypyriprole (CAS 1771741-86-6), fluensulfone, flufenerime, flufenoxystrobin, flufiprole, fluhexafone, fluopyram, flupyrimine, fluralaner, fufenozide, flupentiofenox , guadipyr, heptafluthrin, imidaclothiz, iprodione, isocycloseram, kappa-bifenthrin, kappa-tefluthrin, lotilaner, meperfluthrin, nicofluprole (CAS 1771741-86-6), oxazosulfyl, paichongding, pyridalyl, pyrifluquinazone, pyriminostrobin, sarolaner, spidoxamate, spirobudiclofen., tetramethylfluthrin , tetrachlorantraniliprole, tigolaner, tioxazafen, thiofluoximate, tyclopyrazoflor, iodomethan; also preparations based on Bacillus firmus (1-1582, Votivo) and azadirachtin (BioNeem), as well as the following compounds: l-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sul- fmyl]phenyl}-3-(trichloromethyl)-1H-1,2,4-triazole-5-amine (known from WO2006/043635) (CAS 885026-50-6), 2-chloro-N-[2-{ l-[(2E)-3-(4-chlorophenyl)prop-2-en-l-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006/003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0), 3-(4-Chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-l,8-diazaspiro[4.5]dec-3-en-4-yl -ethyl carbonate (known from EP 2647626) (CAS1440516-42-6), PF1364 (known from JP2010/018586) (CAS 1204776-60-2), (3E)-3-[l-[(6-chloro-3- pyridyl)methyl]-2-pyridylidene]-l,l,l-trifluoropropan-2-one (known from WO2013/144213) (CAS 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl] -1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carbo xamide (known from WO2010/051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro -2-pyridyl)pyrazole-3-carboxamide (known from CN103232431) (CAS 1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3 -isoxazolyl]-2-methyl-N-(cis-l-oxido-3-thietanyl)benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3- isoxazolyl]-2-methyl-N-(trans-l-oxido-3-thietanyl)benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl) -3-isoxazolyl]-2-methyl-N-(cis-l-oxido-3-thietanyl)benzamide (known from WO 2013/050317 A1) (CAS 1332628-83-7), N-[3-chloro-l -(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide, (+)-N-[3-chloro-1 -(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide and (-)-N-[3-chloro-1 -(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfmyl]propanamide (known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1) (CAS 1477923-37-7), 5-[[(2E)-3-chloro-

2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-IH-pyrazol-

3 -carbonitrile (known from CN 101337937 A) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6- [(methylamino)thioxomethyl]phenyl] - 1 -(3 - chloro-2-pyridinyl)-1H-pyrazol-5-carboxamide, (Liudaibenj ia-xuanan, known from CN 103109816 A) (CAS 1232543-85-9); N -[4-Chloro-2-[[(1,1-dimethyl-ethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H- pyrazole-5-carboxamide (known from WO 2012/034403 A1) (CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-

4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from WO 2011/085575 A1) (CAS 1233882-22-8), 4-[3-[2,6-Dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)pyrimidine ( known from CN 101337940 A) (CAS 1108184-52-6); (2E)- and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide (known from CN 101715774A) (CAS 1232543-85-9); Cyclopropanecarboxylic acid 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl ester (known from CN 103524422 A) (CAS 1542271-46-4); (4aS)-7-Chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]indeno[1,2-e][1,3 ,4]oxadiazine-4a(3H)-carboxylic acid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2); 6-Deoxy-3-O-ethyl-2,4-di-O-methyl-1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl] - 1H-1,2,4-triazol-3-yl]phenyl]carbamate]-aL-mannopyranose (known from US 2014/0275503 A1) (CAS 1181213-14-8); 8-(2-Cyclopropylmethoxy-4-trifluoromethylphen- oxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS 1253850-56-4), (8-anti)- 8-(2- Cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3- azabicyclo[3.2.1]octane (CAS 933798-27-7), (8-syn)-8- (2-Cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2. l]octane (known from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8), N-[4-(aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo -l-(3-chloro-2-pyridinyl)- lH-pyrazol-5-carboxamide (known from CN 103265527 A) (CAS 1452877-50-7), 3-(4-chloro-2,6-dimethylphenyl)- 8-methoxy-1-methyl-1,8-diazaspiro[4.5]decan-2,4-dione (known from WO 2014/187846 A1) (CAS 1638765-58-8), 3-(4-chloro-2, 6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl-carboxylic acid ethyl ester (known from WO 2010/066780 A1, WO 2011151146 A1) ( CAS 1229023-00-0), A-[l-(2,6-difluorophenyl)-lH-pyrazol-3-yl]-2-(trifluoromethyl)benzamide (known from WO 2014/053450 A1) (CAS 1594624-87 -9), /V-[2-(2,6-difluorophenyl)-2H-1,2,3-triazol-4-yl]-2-(trifluoromethyl)benzamide (known from WO 2014/053450 A1) (CAS 1594637-65-6). N-[1-(3,5-difluoro-2-pyridinyl)-1H-pyrazol-3-yl]-2-(trifluoromethyl)benzamide (known from WO 2014/053450 A1) (CAS 1594626-19-3). (3A)-3-(2-Chloro-5-thiazolyl)-2,3-dihydro-8-methyl-5,7-dioxo-6-phenyl-5H-thiazolo[3,2-a]pyrimidinium inner salt (known from WO 2018/177970 A1) (CAS 2246757-58-2); 3-(2-Chloro-5-thiazolyl)-2,3-dihydro-8-methyl-5,7-dioxo-6-phenyl-5H-thiazolo[3,2-a]pyrimidinium inner salt (known from WO 2018/177970 A1) (CAS 2246757-56-0); JV-[3-chloro-l-(3-pyridinyl)-lH-pyrazol-4-yl]-2-(methylsulfonyl)propanamide (known from WO 2019/236274 A1) (CAS 2396747-83-2), W |2-bromo-4-| 1.2.2.2-tctrafliorol- l -(trifliioromcthyl)cthyl |-6- (trifluoromethyl)phenyl]-2-fluoro-3-[(4-fluorobenzoyl)amino]benzamide (known from WO 2019059412 Al) (CAS 1207977-87-4).

fungicides

The active ingredients specified here with their “Common Name” are known and are described, for example, in the “Pesticide Manual” (16th edition of the British Crop Protection Council) or can be researched on the Internet (for example: www.alanwood.net/pesticides).

All of the mixing partners mentioned in classes (1) to (15) can optionally form salts with suitable bases or acids if they are able to do so because of their functional groups. All of the fungicidal mixing partners mentioned in classes (1) to (15) can optionally include tautomeric forms.

1) Inhibitors of ergosterol biosynthesis, for example (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1009) flutriafol, (1010) imazalil, (1011) imazalil sulfate, (1012) ipconazole, (1013) metconazole, (1014) myclobutanil, (1015) paclobutrazol, (1016) prochloraz, (1017) propiconazole, ( 1.018) prothioconazole, (1.019) pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025) triticonazole, (1.026) (lR,2S,5S)- 5-(4-chloro-benzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.027)(1S,2R,5R)- 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, ( 1.028) (2R)-2-( 1 -chlorocyclopropyl )-4-[( 1R)-2,2-dichlorocyclopropyl]-1-( 1H- 1 ,2,4-triazol-1-yl)butan-2-ol, ( 1.029) (2R)- 2-( 1-chlorocyclopropyl)-4-[( 1 S)-2,2 -dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1,030)

(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.031)

(2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.032) (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butane-2- ol, (1.033) (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-l-(1H-1,2,4-triazol-1-yl)propan-2-ol , (1.034) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035) ( S ) - [ 3 -(4-chloro-2-fluorophenyl)-5 -(2,4-difluorophenyl)-1 ,2-oxazol-4-yl] (pyridin-3 -yl)methanol,

( 1.036) [3 -(4-chloro-2-fluorophenyl)-5 -(2,4-difluorophenyl)-1 ,2-oxazol-4-yl] (pyridin-3 -yl)methanol, (1.037) l- ({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4- triazole, (1.038) l-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl) -lH-

1.2.4-triazole, (1.039) 1 - {[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl } - 1H-1,2,4-triazole- 5 -yl thiocyanate, (1.040) l-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-lH-

1.2.4-triazol-5-yl thiocyanate, (1.041) l-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}- lH-l,2,4-triazol-5-yl thiocyanate, (1,042) 2-[(2R,4R,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptane- 4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.043) 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1,044) 2-

[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4- triazole 3-thione, (1,045) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro -3H-1,2,4-triazole-3-thione, (1,046) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trime - ethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, ( 1.047) 2-[(2S,4R,5S)-1-(2,4- dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.048) 2-[(2S,4S ,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione , (1.049) 2-[(2S,4S,5S)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H- 1,2,4-triazole-3-thione, (1,050) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro -3H-1,2,4-triazole-3-thione, (1.051) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazole- 1 -yl)propan-2-ol, (1,052) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butane-2 -ol, (1.053) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butane -2-ol, (1.054) 2-[4-(4-chlorophenoxy)-

2-(trifluoromethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)pentan-2-ol, (1.055) mefentrifluconazole, (1.056) 2-{[3-(2-chlorophenyl) -2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.057) 2-{[rel(2R, 3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-

1.2.4-triazole-3-thione, (1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl }-2,4-dihydro-3H-l,2,4-triazole-3-thione, (1.059) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-l-(lH-

1.2.4-triazol- 1 -ylmethyl)cyclopentanol, ( 1,060) 5 -(allylsulfanyl)- 1 - {[3 -(2-chlorophenyl)-2-(2,4-difluoro-phenyl)oxiran-2-yl] methyl } - 1H- 1 ,2,4-triazole, (1.061) 5 -(allylsulfanyl)- 1 - { [rel(2R,3R)-3 -(2-chlorophenyl)-2-(2,4- difluorophenyl)oxiran-2-yl]methyl } - 1H- 1 ,2,4-triazole, ( 1.062) 5 -(allylsulfanyl)- 1 - { [rel(2R,3S)-

3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1,063) N'-(2,5 -dimethyl -

4-{[3-(1,1,2,2-Tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.064) N'-(2,5-dimethyl-4-{[3 -(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1,065) N'-(2,5-dimethyl-4-{[3-(2,2,3 ,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.066) N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl) -N-ethyl-N-methylimidoformamide, (1.067) N'-(2,5-dimethyl-4-{3-[(l,l,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N- ethyl-N-methylimidoformamide, ( 1.068) N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide , (1.069) N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.070 ) N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.071) N'-(2,5-dimethyl- 4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (1.072) N'-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimeth ylphenyl)-N-ethyl-N-methylimidoformamide, (1.073) N'-(4-{3-[(difluoromethyl)sulfanyl]phen-oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, ( 1.074) N'-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide, (1.075) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide, (1.076) N'-{5 -bromo-6-[(lR)-l-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.077) N'-{5-bromo- 6-[(15)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidofomianide, (1.078) N'-{5-bromo-6-[ (cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.079) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl) oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1,080) N'-{5-bromo-6-[ 1 -(3 ,5 -difluorophenyl)ethoxy]-2-methylpyridin- 3-yl } -N- ethyl-N-methylimidoformamide, (1.081) Ipfentrifluconazole, (1.082) 2-[4-(4-Chlorophenoxy)-2-(trifluoromethyl)phenyl]-l-(lH-l,2,4-triazole-l- yl)propan-2-ol, (1,083) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan- 2-ol, (1,084) 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.085) 3-[2-(1-Chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile and (1.086) 4-[[6-[ rac-(2R)-2-(2,4-Difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl ] -3 -pyridyl]oxy]benzonitrile.

2) Respiratory chain inhibitors at complex I or II, for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008 ) furametpyr, (2.009) isofetamide, (2.010) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimeric racemate 1RS ,4SR,9SR), (2.013) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1R,4S,9R ), (2.015) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.016) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019) pydiflumetofen, ( 2.020) pyraziflumide, (2.021) sedaxane, (2.022) l,3-dimethyl-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-lH-pyrazol-4- carboxamide, (2.023)

1,3-dimethyl-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazole-4-carboxamide, (2.024)

1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.025) 1-methyl-3 -(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (2,026) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3 -trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.027) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro - 1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.028) Inpyrfluxam, (2.029) 3-(Difluoromethyl)-1-methyl-N-[(3S)-1,1,3 -trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.030) fluindapyr, (2.031) 3-(difluoromethyl)-N-[(3R)-7 -fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.032) 3-(Difluoromethyl)-N-[ (3S)-7-fluoro-

1.1.3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.033) 5,8-difluoro-N-[2-(2- fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.034) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl- 3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (2.035) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)- 5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (2.036) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(dichloromethyl)-5-fluoro-l-methyl- lH-pyrazole-4-carboxamide, (2.037) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl- lH-pyrazole-4-carboxamide, ( 2.038) N-(5-Chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (2.039) N-[(lR ,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalin-5 -yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, ( 2.040) N -[(1S,4R)-9-(Dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalin-5-yl]-3-(difluoromethyl)- l-methyl- lH-pyrazole-4-carboxamide, (2.041 )N-[ 1 -(2,4-Dichlorophenyl)-1-methoxypropan-2-yl]-3 -(difluoro-methyl)-l -methyl- lH -pyrazole-4-carboxamide, (2.042) N -[2-Chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5 -fluoro- 1 -methyl- lH -pyrazole-4 -carboxamide, (2.043) N -[3 -Chloro-2-fluoro-6-(trifluoromethyl)benzyl] -N -cyclopropyl-3 -(difluoromethyl)-5 -fluoro- 1 -methyl- lH -pyrazole-4 -carboxamide, (2.044) N -[5-Chloro-2-(trichloromethyl)benzyl]-N-cyclopropyl-3-(dichloromethyl)-5-fluoro-1-methyl-1H-pyrazole-4- carboxamide, (2.045) N-Cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (2.046 ) N -Cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-l -methyl- lH -pyrazole-4-carboxamide, (2.047) N -Cyclopropyl-3-(difluoromethyl )-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.048) N-cyclopropyl-3-(difluoro-methyl)-5-fluoro-N -(2-isopropylbenzyl)-l-methyl-lH-pyrazole-4-carbothioamide, (2.049) N-cyclopropyl-

3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2,050) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N -(5-fluoro-2-isopropylbenzyl)-l-methyl-lH-pyrazole-4-carboxamide, (2.051) N -cyclopropyl-3 -(difluoromethyl)-N-(2-ethyl-4,5 -dimethylbenzyl) - 5 -fluoro- 1 -methyl- IH-pyrazole-

4-carboxamide, (2.052) N -Cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-l-methyl- lH-pyrazole-4-carboxamide, (2.053) N - Cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl- lH-pyrazole-4-carboxamide, (2.054) N-cyclopropyl-N-(2-cyclopropyl- 5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055) N -cyclopropyl-N-(2-cyclopropyl- 5 -methylbenzyl)-3 -(difluoromethyl )-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole -4-carboxamide, (2.057) pyrapropoyn.

3) Inhibitors of the respiratory chain at complex III, for example (3.001) ametoctradine, (3.002) amisulbromine, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamide, (3.007) dimoxystrobin, (3.008) enoxastrobin , (3.009) famoxadone, (3.010) fenamidone, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013) kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin, (3.018) ) pyrametostrobin, (3.019) pyraoxystrobin, (3.020) trifloxystrobin, (3.021) (2E)-2-{2-[({[(lE)-l-(3-{[(E)-l-fluoro- 2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.022)(2E,3Z)-5-{ [ l-(4-chloro - phenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.023) (2R)-2-{2-[(2,5-dimethylphenoxy). )methyl]phenyl} -2 -methoxy -N-methylacetamide, (3.024) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl} -2 -methoxy -N-methylacetamide, ( 3.025) fenpicoxamide, (3.026) mandestrobin, (3.027) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (3.028)(2E,3Z)-5-{[l-(4-chloro-2-fluorophenyl)-lH -pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) {5-[3-(2,4-dimethylphenyl)-1 H -pyrazol-1-yl ]-2-methylbenzyl}carbamic acid methyl ester, (3.030) methyltetraprole, (3.031) flory ipicoxamide.

4) Inhibitors of mitosis and cell division, for example (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) pencycuron, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl )-6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.012) 4-(2- bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.013) 4-(2-bromo-4-fluorophenyl)-N-(2 -bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.014) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl -lH-pyrazol-5-amine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5- amine, (4.016) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.017) 4-(2-bromo-4 -fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.018) 4-(2-chloro-4-fluoro-phenyl)-N-(2,6- difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.019) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl- lH-pyrazol-5-amine, (4.020) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (4.021) 4-(2-chloro-4-chlorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.022) 4-(4-chlorophenyl)-5-( 2,6-difluorophenyl)-3,6-dimethylpyridazine, (4.023) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-l,3-dimethyl-lH-pyrazole- 5-amine, (4.024) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.025) N-(4-chloro -2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine.

5) Compounds that can act at several sites ("Multisite Action"), for example (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate , (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper(2+) sulfate, (5.010) dithianone, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) metiram-zinc, (5.017) oxin-copper, (5.018) propineb, (5.019) sulfur and sulfur preparations including calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022) ziram, (5.023) 6- ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][1,4]dithiino[2,3-c][1,2]thiazole-3- carbonitrile .

6) Compounds capable of inducing host defense responses, for example (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.

7) Inhibitors of amino acid and/or protein biosynthesis, for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3-(5-fluoro- 3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

8) Inhibitors of ATP production, for example (8.001) silthiofam.

9) Inhibitors of cell wall synthesis, for example (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamide, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)- 3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.009)(2Z)-3 -(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-one.

10) Inhibitors of lipid and membrane synthesis, for example (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.

11) Inhibitors of melanin biosynthesis, for example (11.001) tricyclazole, (11.002) {3-Methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamic acid 2,2,2-trifluoroethyl ester.

12) Inhibitors of nucleic acid synthesis, for example (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam). 13) Inhibitors of signal transduction, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozoline.

14) Compounds that can act as uncouplers, for example (14.001) fluazinam, (14.002) methyldinocap.

15) Other fungicides selected from the group consisting of (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazine, (15.004) capsimycin, (15.005) carvone, (15.006) quinomethionate, (15.007) cufraneb, (15.008) cyflufenamide, (15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil, (15.012) fosetyl aluminum, (15.013) fosetyl calcium, (15.014) fosetyl sodium, (15.015) methyl isothiocyanate, (15.016) metrafenon (15.017) mildiomycin, (15.018) natamycin, (15.019) nickeldimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021) oxamocarb, (15.022) oxathiapiproline, (15.023) oxyfenthiin, (15.024) pentachlorophenol and salts, (15.025) ) phosphorous acid and its salts, (15.026) propamocarb fosetylate, (15.027) pyriofenone (chlazafenone), (15.028) tebufloquine, (15.029) tecloftalam, (15.030) tolnifanide, (15.031) l-(4-{4- [(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2 -[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]ethanone, (15.03 2) l-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-l,3-thiazole-2- yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034) Dipymetitrone, (15.035) 2-[3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]-l-[4-(4-{5-[2-(prop-2-yn- 1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15,036) 2-[3, 5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4, 5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15,037) 2-[3,5-bis(difluoromethyl)-1H- pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazole -3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]-ethanone, (15,038) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl ]quinazoline, (15.039) methanesulfonic acid-2-{(5R)-3-[2-(l-{[3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidine-4- yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazo l-5 -yl } -3 -chlorophenyl ester, ( 15,040) methanesulfonic acid-2- { (5 S)-3 -[2-( 1 - { [3 ,5 - bis(difluoromethyl)-lH -pyrazol-l-yl ]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl ester, (15.041) Ipflufenoquine, (15.042) 2-{2-Fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.043) fluoxapiproline, (15.044) methanesulfonic acid-2-{3-[2 -(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}-3-chlorophenyl ester, (15.044) fluoxapiproline, (15.045) 2-phenylphenol and salts, (15.046) 3-(4,4,5-trifluoro-3,3-dimethyl-3, 4-dihydroisoquinolin-l-yl)quinoline, (15.047) quinofumeline, (15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(lH)-one), ( 15.049) 4-Oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.050) 5-amino-l,3,4-thiadiazole-2-thiol, (15.051) 5-chloro-N'-phenyl-N '-(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide, (15.052) 5-Fluoro-2-[(4-fluorobenzyl)oxy]pyrimidine-4-a-mi n, (15.053) 5-Fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054) 9-Fluoro-2,2-dimethyl-5-(quinolin-3-yl)- 2,3-dihydro-l,4-benzoxazepine, (15.055) {6-[({[(Z)-(l-methyl-lH-tetrazol-5-yl)(phenyl)methylene]amino}oxy) methyl]pyridin-2-yl}carbamic acid but-3-yn-l-yl ester, (15.056) (2Z)-3-Amino-2-cyano-3-phenylacrylic acid ethyl ester, (15.057) phenazine-1-carboxylic acid, (15.058) 3 ,4,5- propyl trihydroxybenzoate, (15,059) quinolin-8-ol, (15,060) quinolin-8-ol sulfate (2:1), (15,061) { 6-[( { [( 1 -methyl- lH -tetrazol-5 -yl)(phenyl )methylene]amino}oxy)methyl]pyridin-2-yl}carbamic acid - tert, -butyl ester, (15,062) 5 -Fluoro-4-imino-3 -methyl- 1 -[(4-methylphenyl)sulfonyl] -3 , 4-dihydropyrimidin-2(lH)-one, (15.063) aminopyrifene, (15.064) (N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylimidoformamide), (15.065) (N'-(2-Chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide), (15.066) (2-{2-[(7,8-difluoro-2 -methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol), (15.067) (5-bromo-1-(5,6-dimethylpyridin-3-yl)-3,3-dimethyl-3 ,4-dihydroisoquinoline), ( 15,068) (3 -(4,4-difluoro-5,5 -dimethyl -4,5 -dihydrothieno[2,3 -c]pyridin-7 -yl)quinoline), (15,069) ( 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline), (15,070) 8-fluoro-3-(5 -fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinolone, (15.071) 8-Fluoro-3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinolone, (15,072) 3-(4,4-Difluoro-3,3-dimethyl -3,4-dihydroisoquinolin-1-yl)-8-fluoroquinoline, (15.073) (N-Methyl-N-phenyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl ]benzamide), (15.074) (Methyl{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}carbamate), (15.075) (N-{4-[5-(Trifluorme - thyl)-1,2,4-oxadiazol-3-yl]benzyl}cyclopropanecarboxamide), (15,076) N -methyl -4-(5-(trifluoromethyl)-

1.2.4-oxadiazol-3-yl]benzamide, (15.077) N -[(E)-Methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-o-xadiazol-3-yl]benzamide, (15.078) N-[(Z)-Methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, ( 15.079) N-[4-[5-(trifluoromethyl) - 1,2,4-oxadiazol-3-yl]phenyl]-cyclopropanecarboxamide, (15,080) N-(2-Fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl] benzamide, (15,081) 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-acetamide, (15,082) N -allyl -N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]acetamide, (15,083) N-[(E)-N-methoxy-C-methyl- carbonimidoyl]-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15,084) N -[(Z)-N-Methoxy-C-methyl-carbonimidoyl]-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15,085) N -Allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3 -yl]phenyl]methyl]propanamide, (15.086) 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl] pyrrolidin-2-one, (15,087) N -methyl-4-[5-(trif fluoromethyl)-1,2,4-oxadiazol-3-yl]-benzenecarbothioamide, (15.088) 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-o-xadiazol- 3-yl]phenyl]methyl]pyrrolidin-2-one, (15,089) N-((2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-o-xadiazol-3-yl] phenyl]methyl]-3,3,3-trifluoro-propanamide, (15,090) 1-Methoxy-1-methyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazole-3 -yl]phenyl]methyl]urea, (15.091) l,l-diethyl-3-[[4-[5-(trifluoromethyl}-

1.2.4-oxadiazol-3-yl]phenyl]methyl]urea, (15.092) N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.093) N -Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, ( 15.094) 1 -Methoxy-3 -methyl - 1 -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.095) N-Methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl)cyclopropanecarboxamide, (15,096) N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl}-1,2,4- oxadiazol-3-yl]phenyl]methyl]propanamide, (15,097) N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl] methyl]propanamide, (15,098) 1 -Methoxy-3 -methyl- 1 -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15,099) l ,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15,100) 3-ethyl-1-methoxy-1 -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.101) l-[[4-[5-(trifluoromethyl)-l, 2,4-oxadia inch-3- yl]phenyl]methyl]piperidin-2-one, (15.102) 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl] isooxazolidin-3-one, (15.103) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.104) 3,3-dimethyl-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.105) l-[ [3-Fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one, (15.106) 4,4-dimethyl-2-[ [4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.107) 5,5-dimethyl-2-[[4-[ 5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.108) (l-{4-[5-(trifluoromethyl)-l,2, 4-oxadiazol-3-yl]benzyl}-1H-pyrazol-4-yl)acetic acid ethyl ester, (15.109) N,N-dimethyl- 1 -{4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzyl}-1H-1,2,4-triazole-3-amine and (15.110) N-{2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzyl}butanamide.

Biological pest control agents as mixture components

The compounds of formula (I) can be combined with biological pest control agents.

Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts and products formed by microorganisms, including proteins and secondary metabolites.

Biological pest control agents include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria which act as biological insecticides, fungicides or nematicides.

Examples of such bacteria that are used or can be used as biological pest control agents are:

Bacillus amyloliquefaciens strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, in particular strain GB34 (Accession No. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, in particular strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002 (Accession No. NRRL B-50421), Bacillus thuringiensis, in particular B. thuringiensis subsp. israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode)-PR3 (accession number ATCC SD-5834), Streptomyces microflavus strain AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus strain AQ 6047 (accession number NRRL 30232).

Examples of fungi and yeasts that are used or can be used as biological pest control agents are: Beauveria bassiana, especially strain ATCC 74040, Coniothyrium minitans, especially strain CON/M/91-8 (Accession No. DSM-9660), Lecanicillium spp., especially strain HRO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanii) , in particular strain KV01, Metarhizium anisoplicie, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (heu: Isarici fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain VI 17b, Trichoderma atroviride, in particular strain SCI (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM 1-952).

Examples of viruses that are or can be used as biological pest control agents are:

Adoxophyes orana (codling moth) granulovirus (GM), Cydia pomonella (codling moth) granulovirus (GM), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet owl moth) mNPV, Spodoptera frugiperda (armyworm) mNPV, Spodoptera littoralis (African cottonworm) NPV.

It also includes bacteria and fungi that are added to plants or plant parts or plant organs as 'inoculants' and promote plant growth and plant health through their special properties. Examples are:

Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., especially Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., in particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp. .

Examples of plant extracts and such products formed by microorganisms, including proteins and secondary metabolites, which are or can be used as biological pest control agents are:

Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armor-Zen, Dryopteris fdix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum/Pyrethrine, Quassia amara, Quercus, Quillaja, Regalia, "Requiem ™ Insecticide", Rotenone, Ryania/Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen -Extract, in particular rapeseed or mustard powder, and bioinsecticidal/acaricidal active ingredients obtained from olive oil, in particular unsaturated fatty/carboxylic acids with carbon chain lengths C16-C20 as active ingredients such as contained in the product with the trade name FLiPPER®. Safeners as mixture components

The compounds of formula (I) can be combined with safeners, such as benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormide, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenime, furilazole, isoxadifen (-ethyl ), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)- l-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-l,3-o-xazolidine (CAS 52836-31-4).

plants and parts of plants

All plants and parts of plants can be treated according to the invention. Plants are understood to mean all plants and parts of plants, such as desired and undesired wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, tomatoes , peppers, cucumbers, melons, carrots, watermelons, onions, lettuce, spinach, leeks, beans, Brassica oleracea (e.g. cabbage) and other types of vegetables, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes). Crop plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including transgenic plants and including plant varieties that can or cannot be protected by plant variety rights. Plants should be understood to mean all stages of development such as seeds, cuttings, young (immature) plants through to mature plants. Plant parts are to be understood as meaning all above-ground and subterranean parts and organs of plants such as shoots, leaves, flowers and roots, with leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes being listed as examples. The plant parts also include harvested plants or harvested plant parts and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, cuttings and seeds.

The treatment according to the invention of the plants and parts of plants with the compounds of the formula (I) is carried out directly or by the action of the compounds on the environment, the living space or the storage space according to the usual treatment methods, e.g. B. by dipping, spraying, vaporizing, nebulizing, sprinkling, brushing, injecting and in the case of propagation material, especially seeds, also by one or more layers of encasing.

As already mentioned above, all plants and parts thereof can be treated according to the invention. In a preferred embodiment, plant species and plant cultivars occurring in the wild or obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and parts thereof are treated. In a further preferred embodiment, transgenic plants and plant varieties, optionally in combination with genetic engineering methods conventional methods (Genetically Modified Organisms) and treated parts thereof. The term "parts" or "parts of plants" or "plant parts" has been explained above. Plants of the plant varieties that are commercially available or in use are particularly preferably treated according to the invention. Plant varieties are plants with new properties (“traits”) that have been obtained through conventional breeding, through mutagenesis or through recombinant DNA techniques. This can be varieties, breeds, organic and genotypes.

Transgenic plant, seed treatment and integration events

According to the invention, the compounds of the formula (I) can advantageously be used for treating transgenic plants, plant cultivars or plant parts which have received genetic material which imparts advantageous and/or useful properties (traits) to these plants, plant cultivars or plant parts. It is therefore contemplated to combine the present invention with one or more recombinant traits or transgenic events, or a combination thereof. For the purposes of the present application, a transgenic event results from the insertion of a specific recombinant DNA molecule into a specific position (locus) in the chromosome of the plant genome. The insertion creates a new DNA sequence, termed an "event", which is characterized by the inserted recombinant DNA molecule and some amount of genomic DNA immediately adjacent to the inserted DNA/flanking the inserted DNA at both ends. Such traits or transgenic events include, without limitation, resistance to pests, water use efficiency, yield performance, drought tolerance, seed quality, improved nutrient quality, hybrid seed production and herbicide tolerance, the trait in relation to a plant of such a trait or a such a transgenic event is absent, is measured. Concrete examples of such advantageous and/or useful properties (traits) are better plant growth, vitality, stress tolerance, standing ability, resistance to storage, nutrient uptake, plant nutrition and/or yield, in particular improved growth, increased tolerance to high or low temperatures, increased tolerance to Drought or water or soil salinity, increased flowering, easier harvesting, accelerated ripening, higher yields, higher quality and/or higher nutritional value of the harvested products, better shelf life and/or workability of the harvested products and increased resistance or tolerance to animal and microbial pests such as against insects, arachnids, mites and snails.

Of the DNA sequences coding for proteins conferring resistance or tolerance properties to such animal and microbial pests, especially insects, the genetic material of Bacillus thuringiensis coding for the Bt proteins, which is described extensively in the literature, should be mentioned in particular described and well known to those skilled in the art. Proteins extracted from bacteria such as Photorhabdus (WO97/17432 and WO98/08932) should also be mentioned. In particular, mention should be made of Bt Cry or VIP proteins, which include CrylA, CrylAb, CrylAc, CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF proteins or toxic fragments thereof , and also hybrids or combinations thereof, in particular the CrylF protein or hybrids derived from a CrylF protein (e.g. hybrid CrylA-CrylF proteins or toxic fragments thereof), the CrylA-type proteins or toxic fragments thereof, preferably the Cry 1 Ac protein or hybrids derived from the Cry 1 Ac protein (e.g. hybrid CrylAb-CrylAc proteins) or the CrylAb or Bt2 protein or toxic fragments thereof, the Cry2Ae, Cry2Af or Cry2Ag proteins or toxic fragments thereof, the Cry 1A. 105 protein or a toxic fragment thereof, the VIP3Aal9 protein, the VIP3Aa20 protein, the VIP3A proteins produced at the COT202 or COT203 cotton events, the VIP3Aa protein or a toxic fragment thereof, as in Estruch et al. (1996), Proc Natl Acad Sei US A. 28;93(11):5389-94, the Cry proteins as described in WO2001/47952, the insecticidal proteins from Xenorhabdus (as described in WO98/50427), Serratia (in particular from 'S', entomophila)' or strains of the Photorhabdus Xd, such as Tc proteins from Photorhabdus as described in WO98/08932. This also includes all variants or mutants of one of these proteins that differ in a few amino acids (1-10, preferably 1-5) from any of the above sequences, in particular the sequence of their toxic fragment, or to a transit peptide such as a plastid transit peptide or other protein or peptide are fused.

Another and particularly prominent example of such properties is conferred tolerance to one or more herbicides, for example imidazolinones, sulphonylureas, glyphosate or phospinothricin. Of the DNA sequences coding for proteins that give the transformed plant cells and plants tolerance properties to certain herbicides, the bar or PAT gene or the Streptomyces coelicolor gene, which is described in WO2009/152359 and which tolerance to Glufonsin herbicides confers a gene encoding an appropriate EPSPS (5-enolpyruvylshikimate-3-phosphate synthase) that confers tolerance to EPSPS-targeted herbicides, particularly herbicides such as glyphosate and its salts, a for glyphosate N-acetyltransferase gene encoding or a gene encoding glyphosate oxoreductase may be mentioned. Other suitable herbicide tolerance traits include at least one ALS (acetolactate synthase) inhibitor (e.g. WO2007/024782), a mutant Arabidopsis ALS/AHAS gene (e.g. US Patent 6,855,533), genes encoding 2,4-D monooxygenases, tolerance to 2,4-D (2,4-dichlorophenoxyacetic acid) and genes encoding dicamba monooxygenases that confer tolerance to dicamba (3,6-dichloro-2-methoxybenzoic acid).

Further and particularly emphasized examples of such properties are an increased resistance to phytopathogenic fungi, bacteria and/or viruses, which, for example, goes back to systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and also resistance genes and the correspondingly expressed proteins and toxins.

Particularly useful transgenic events in transgenic plants or plant cultivars, which can preferably be treated according to the invention, include Event 531/PV-GHBK04 (cotton, insect control, described in WO2002/040677), Event 1143-14A (cotton, insect control, not deposited, described in WO2006/128569); Event 1143-51B (cotton, insect control, not deposited, described in WO2006/128570); Event 1445 (Cotton, herbicide tolerance, not deposited, described in US-A 2002-120964 or WO2002/034946); Event 17053 (rice, herbicide tolerance, deposited as PTA-9843, described in WO2010/117737); Event 17314 (rice, herbicide tolerance, deposited as PTA-9844, described in WO2010/117735); Event 281-24-236 (Cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in WO2005/103266 or US-A 2005-216969); Event 3006-210-23 (Cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in US-A 2007-143876 or WO2005/103266); Event 3272 (maize, quality attribute deposited as PTA-9972, described in WO2006/098952 or US-A 2006-230473); Event 33391 (Wheat, herbicide tolerance, deposited as PTA-2347, described in WO2002/027004), Event 40416 (Maize, insect control - herbicide tolerance, deposited as ATCC PTA-11508, described in WO 11/075593); Event 43A47 (Maize, insect control - herbicide tolerance, deposited as ATCC PTA-11509, described in WO2011/075595); Event 5307 (Maize, insect control, deposited as ATCC PTA-9561, described in WO2010/077816); Event ASR-368 (Bentgrass, herbicide tolerance, deposited as ATCC PTA-4816, described in US-A 2006-162007 or WO2004/053062); Event B16 (Maize, herbicide tolerance, not deposited, described in US-A 2003-126634); Event BPS-CV127-9 (Soybean, herbicide tolerance, deposited as NCIMB No. 41603, described in WO2010/080829); Event BLR1 (rapeseed, restoration of male sterility, deposited as NCIMB 41193, described in WO2005/074671), Event CE43-67B (cotton, insect control, deposited as DSM ACC2724, described in US-A 2009-217423 or WO2006/128573); Event CE44-69D (cotton, insect control, not deposited, described in US-A 2010-0024077); Event CE44-69D (cotton, insect control, not deposited, described in WO2006/128571); Event CE46-02A (cotton, insect control, not deposited, described in WO2006/128572); Event COT102 (Cotton, insect control, not deposited, described in US-A 2006-130175 or WO2004/039986); Event COT202 (Cotton, insect control, not deposited, described in US-A 2007-067868 or WO2005/054479); Event COT203 (Cotton, insect control, not deposited, described in WO2005/054480); ); Event DAS21606-3/1606 (soybean, herbicide tolerance, deposited as PTA-11028, described in WO2012/033794), Event DAS40278 (corn, herbicide tolerance, deposited as ATCC PTA-10244, described in WO2011/022469); Event DAS-44406-6 / pDAB8264.44.06.1 (soybean, herbicide tolerance, deposited as PTA-11336, described in WO2012/075426), Event DAS-14536-7 /pDAB8291.45.36.2 (soybean, herbicide tolerance, deposited as PTA -11335, described in WO2012/075429), Event DAS-59122-7 (maize, insect control - herbicide tolerance, deposited as ATCC PTA 11384, described in US-A 2006-070139); Event DAS-59132 (Maize, insect control - herbicide tolerance, not deposited, described in WO2009/100188); Event DAS68416 (Soybean, herbicide tolerance, deposited as ATCC PTA-10442, described in WO2011/066384 or WO2011/066360); Event DP-098140-6 (Maize, herbicide tolerance, deposited as ATCC PTA-8296, described in US-A 2009-137395 or WO 08/112019); Event DP-305423-1 (soybean, quality attribute, not deposited, described in US-A 2008-312082 or WO2008/054747); Event DP-32138-1 (Maize, hybridization system deposited as ATCC PTA-9158, described in US-A 2009-0210970 or WO2009/103049); Event DP-356043-5 (Soybean, herbicide tolerance, deposited as ATCC PTA-8287, described in US-A 2010-0184079 or WO2008/002872); Event EE-I (eggplant, insect control, not deposited, described in WO 07/091277); Event Fil 17 (Maize, herbicide tolerance, deposited as ATCC 209031, described in US-A 2006-059581 or WO 98/044140); Event FG72 (soybean, herbicide tolerance, deposited as PTA-11041, described in WO2011/063413), Event GA21 (corn, herbicide tolerance, deposited as ATCC 209033, described in US-A 2005-086719 or WO 98/044140); Event GG25 (Maize, herbicide tolerance, deposited as ATCC 209032, described in US-A 2005-188434 or WO98/044140); Event GHB119 (Cotton, insect control - herbicide tolerance, deposited as ATCC PTA-8398, described in WO2008/151780); Event GHB614 (Cotton, herbicide tolerance, deposited as ATCC PTA-6878, described in US-A 2010-050282 or WO2007/017186); Event GJ11 (Maize, herbicide tolerance, deposited as ATCC 209030, described in US-A 2005-188434 or WO98/044140); Event GM RZ13 (sugar beet, virus resistance, deposited as NCIMB-41601, described in WO2010/076212); Event H7-1 (sugar beet, herbicide tolerance, deposited as NCIMB 41158 or NCIMB 41159, described in US-A 2004-172669 or WO 2004/074492); Event JOPLIN1 (wheat, disease tolerance, not deposited, described in US-A 2008-064032); Event LL27 (Soybean, herbicide tolerance, deposited as NCIMB41658, described in WO2006/108674 or US-A 2008-320616); Event LL55 (soybean, herbicide tolerance, deposited as NCIMB 41660, described in WO 2006/108675 or US-A 2008-196127); Event LLcotton25 (Cotton, herbicide tolerance, deposited as ATCC PTA-3343, described in WO2003/013224 or US-A 2003-097687); Event LLRICE06 (Rice, herbicide tolerance, deposited as ATCC 203353, described in US 6,468,747 or WO2000/026345); Event LLRice62 (rice, herbicide tolerance, deposited as ATCC 203352, described in WO2000/026345), Event LLRICE601 (rice, herbicide tolerance, deposited as ATCC PTA-2600, described in US-A 2008-2289060 or WO2000/026356); Event LY038 (corn, quality attribute deposited as ATCC PTA-5623, described in US-A 2007-028322 or WO2005/061720); Event MIR162 (Maize, insect control, deposited as PTA-8166, described in US-A 2009-300784 or WO2007/142840); Event MIR604 (Maize, insect control, not deposited, described in US-A 2008-167456 or WO2005/103301); Event MON15985 (Cotton, insect control deposited as ATCC PTA-2516, described in US-A 2004-250317 or WO2002/100163); Event MON810 (corn, insect control, not deposited, described in US-A 2002-102582); Event MON863 (Maize, insect control, deposited as ATCC PTA-2605, described in WO2004/011601 or US-A 2006-095986); Event MON87427 (Maize, pollination control, deposited as ATCC PTA-7899, described in WO2011/062904); Event MON87460 (maize, stress tolerance, deposited as ATCC PTA-8910, described in WO2009/111263 or US-A 2011-0138504); Event MON87701 (Soybean, insect control, deposited as ATCC PTA-8194, described in US-A 2009-130071 or WO2009/064652); Event MON87705 (Soybean, quality attribute - herbicide tolerance, deposited as ATCC PTA-9241, described in US-A 2010-0080887 or WO2010/037016); Event MON87708 (Soybean, herbicide tolerance, deposited as ATCC PTA-9670, described in WO2011/034704); Event MON87712 (soybean, yield, deposited as PTA-10296, described in W02012/051199), Event MON87754 (soybean, quality attribute deposited as ATCC PTA-9385, described in WO2010/024976); Event MON87769 (soybean, quality attribute deposited as ATCC PTA-8911, described in US-A 2011-0067141 or WO2009/102873); Event MON88017 (Maize, insect control - herbicide tolerance, deposited as ATCC PTA-5582, described in US-A 2008-028482 or WO2005/059103); Event MON88913 (Cotton, herbicide tolerance, deposited as ATCC PTA-4854, described in WO2004/072235 or US-A 2006-059590); Event MON88302 (rapeseed, herbicide tolerance, deposited as PTA-10955, described in WO2011/153186), EventMON88701 (cotton, herbicide tolerance, deposited as PTA-11754, described in WO2012/134808), Event MON89034 (maize, insect control, deposited as ATCC PTA - 7455, described in WO 07/140256 or US-A 2008-260932); Event MON89788 (Soybean, herbicide tolerance, deposited as ATCC PTA-6708, described in US-A 2006-282915 or WO2006/130436); Event MSI 1 (rapeseed, pollination control - herbicide tolerance, deposited as ATCC PTA-850 or PTA-2485, described in WO2001/031042); Event MS8 (rapeseed, pollination control - herbicide tolerance, deposited as ATCC PTA-730, described in WO2001/041558 or US-A 2003-188347); Event NK603 (Maize, herbicide tolerance, deposited as ATCC PTA-2478, described in US-A 2007-292854); Event PE-7 (rice, insect control, not deposited, described in WO2008/114282); Event RF3 (rapeseed, pollination control - herbicide tolerance, deposited as ATCC PTA-730, described in WO2001/041558 or US-A 2003-188347); Event RT73 (rapeseed, herbicide tolerance, not deposited, described in WO2002/036831 or US-A 2008-070260); Event SYHT0H2 / SYN-000H2-5 (soybean, herbicide tolerance, deposited as PTA-11226, described in WO2012/082548), Event T227-1 (sugar beet, herbicide tolerance, not deposited, described in WO2002/44407 or US-A 2009-265817 ); Event T25 (maize, herbicide tolerance, not deposited, described in US-A 2001-029014 or WO2001/051654); Event T304-40 (Cotton, insect control - herbicide tolerance, deposited as ATCC PTA-8171, described in US-A 2010-077501 or WO2008/122406); Event T342-142 (cotton, insect control, not deposited, described in WO2006/128568); Event TC1507 (Maize, insect control - herbicide tolerance, not deposited, described in US-A 2005-039226 or WO2004/099447); Event VIP1034 (Maize, insect control - herbicide tolerance, deposited as ATCC PTA-3925, described in WO2003/052073), Event 32316 (Maize, insect control - herbicide tolerance, deposited as PTA-11507, described in WO2011/084632), Event 4114 (maize, Insect Control - Herbicide Tolerance deposited as PTA-11506, described in W02011/084621), Event EE-GM3/FG72 (Soybean, Herbicide Tolerance, ATCC Accession No. PTA-11041) optionally stacked with Event EE-GM1/LL27 or Event EE-GM2 /LL55 (WO2011/063413 A2), Event DAS-68416-4 (soybean, herbicide tolerance, ATCC accession no. PTA-10442, WO2011/066360A1), Event DAS-68416-4 (soybean, herbicide tolerance, ATCC accession no. PTA-10442, WO2011/066384A1), Event DP-040416-8 (corn, insect control, ATCC Accession No. PTA-11508, WO2011/075593 A1), Event DP-043A47-3 (corn, insect control, ATCC Accession No. PTA -11509, WO2011/075595A1), Event DP-004114-3 (corn, insect control, ATCC Accession No. PTA-11506, WO2011/084621A1), Event DP-032316-8 (Ma is, Insect Control, ATCC accession no. PTA-11507, WO2011/084632A1), Event MON-88302-9 (rapeseed, herbicide tolerance, ATCC Accession No. PTA-10955, WO2011/153186A1), Event DAS-21606-3 (soybean, herbicide tolerance, ATCC accession no. PTA-11028, WO2012/033794A2), Event MON-87712-4 (soybean, quality attribute, ATCC Accession No. PTA-10296, WO2012/051199A2), event DAS-44406-6 (soybean, stacked herbicide tolerance, ATCC Accession No. PTA - 11336, WO2012/075426A1), Event DAS-14536-7 (soybean, stacked herbicide tolerance, ATCC Accession No. PTA-11335, WO2012/075429A1), event SYN-000H2-5 (soybean, herbicide tolerance, ATCC Accession No. PTA- 11226, WO2012/082548A2), Event DP-061061-7 (rapeseed, herbicide tolerance, no accession number available, W02012071039A1), Event DP-073496-4 (rapeseed, herbicide tolerance, no accession number available, US2012131692), Event 8264.44.06.1 ( Soybean, Stacked Herbicide Tolerance, Accession No. PTA-11336, WO2012075426A2), Event 8291.45.36.2 (Soybean, Stacked Herbicide Tolerance, Accession No. PTA-11335, WO2012075429A2), Event SYHT0H2 (Soybean, ATCC Accession No. PTA-11335, WO2012075429A2) , Event MON88701 (Cotton, ATCC Accession No. PTA-11754, WO2012/134808A1), Event KK179-2 (Alfalfa, ATCC Accession No. PTA-118 33, W02013/003558A1), Event pDAB8264.42.32.1 (soybean, stacked herbicide tolerance, ATCC accession no. PTA-11993, WO2013/010094A1), Event MZDT09Y (Maize, ATCC Accession No. PTA-13025, WO2013/012775A1).

Furthermore, such a list of transgenic events is provided by the United States Department of Agriculture's (USDA) Animal and Plant Health Inspection Service (APHIS) and can be found on their website on the World Wide Web at aphis.usda.gov. For the present application, the status of this list as it was on the filing date of the present application is relevant.

The genes/events that confer the relevant desired characteristics can also be present in the transgenic plants in combination with one another. Examples of transgenic plants that can be mentioned are important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beet, sugar cane, tomatoes, peas and other types of vegetables, cotton, Tobacco, rapeseed and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), with particular emphasis on corn, soybeans, wheat, rice, potatoes, cotton, sugar cane, tobacco and rapeseed. Traits that are particularly emphasized are the plants' increased resistance to insects, arachnids and snails, and the plants' increased resistance to one or more herbicides.

Commercially available examples of such plants, plant parts or plant seeds which can preferably be treated according to the invention include commercially available products such as plant seeds falling under the GENUITY®, DROUGHTGARD®, SMARTSTAX®, RIB COMPLETE®, ROUNDUP READY ®, VT DOUBLE PRO®, VT TRIPLE PRO®, BOLLGARD II®, ROUNDUP READY 2 YIELD®, YIELDGARD®, ROUNDUP READY® 2 XTEN ^DTM , INTACTA RR2 PRO®, VISTIVE GOLD® and /or XTENDFLEX™ trade names are sold or distributed. Plant protection - types of treatment

The treatment of the plants and parts of plants with the compounds of formula (I) is carried out directly or by affecting their environment, habitat or storage space according to the usual treatment methods, e.g. B. by dipping, spraying, spraying, sprinkling, vaporizing, atomizing, atomizing, scattering, foaming, brushing, spreading, injecting, pouring (drenching), drip irrigation and with propagating material, especially seeds, also by dry dressing, wet dressing, slurry dressing, encrusting , single or multi-layer coating, etc. It is also possible to apply the compounds of formula (I) by the ultra-low volume method or to inject the use form or the compound of formula (I) itself into the soil.

A preferred direct treatment of plants is foliar application, i. H. the compounds of the formula (I) are applied to the foliage, with the frequency of treatment and the application rate being tailored to the infestation pressure of the pest in question.

In the case of systemically active active ingredients, the compounds of the formula (I) also get into the plants via the root system. The plants are then treated by the action of the compounds of formula (I) on the habitat of the plant. This can be done, for example, by drenching, mixing into the soil or the nutrient solution, i. H. the locus of the plant (e.g. soil or hydroponic systems) is drenched with a liquid form of the compounds of formula (I), or by soil application, d. H. the compounds of the formula (I) according to the invention are introduced into the site of the plants in solid form (eg in the form of granules) or by drip application (often also referred to as "chemigation"), ie the compounds of the formula according to the invention (I) are introduced at defined locations near the plants by means of surface or underground drip tubes over specified periods of time together with varying amounts of water. In the case of paddy rice cultures, this can also be done by metering the compound of the formula (I) in a solid application form (eg as granules) into a flooded paddy field.

digital technologies

The compounds according to the invention can be used in combination with, for example, models embedded in computer programs for site-specific crop management, satellite arable farming, precision arable farming or precision farming. Such models support site-specific management of agricultural assets with data from various sources such as soil, weather, crops (e.g. type, growth stage, plant health), weeds (e.g. type, growth stage), diseases, pests, nutrients, water, moisture, biomass, satellite data, yield, etc., with the aim of optimizing profitability, sustainability and environmental protection. In particular, such models can help optimize agronomic decisions, guide the precision of pesticide applications, and record the work performed. For example, one can apply the compounds of the invention to a crop according to an appropriate application protocol when the model modulates the occurrence of a pest and calculates that a threshold has been reached at which it is recommended to apply the compound of the invention to the crop.

Commercially available systems that include agronomic models include The Climate Corporation's FieldScripts™, BASF's Xarvio™, John Deere's AGLogic™, etc.

The compounds of the invention can also be used in combination with smart spray equipment such as spot spray equipment or precision spray equipment attached to a farm vehicle such as a tractor, robot, helicopter, airplane, unmanned aerial vehicle (UAV) such as a drone - or housed, are used. Such equipment usually comprises input sensors (such as a camera) and a processing unit responsible for analyzing the input data and providing a decision, based on the analysis of the input data, to apply the compound of the invention to the crop ( or the weeds) is configured in a specific and precise way. Deploying such smart sprayers usually requires positioning systems (e.g., GPS receivers) to locate the recorded data and control farm vehicles, geographic information systems (GIS) to present the information on understandable maps, and appropriate farm vehicles to operate the required agricultural measure such as spraying.

In one example, pests can be detected from images captured by a camera. In one example, the pests can be identified and/or classified based on these images. With such an identification and/or classification, one can use algorithms for image processing. Such image processing algorithms can use machine learning algorithms such as artificial neural networks, decision trees, and artificial intelligence algorithms. In this way it is possible to use the connections described here only where they are needed.

seed treatment

The control of animal pests by treating the seeds of plants has long been known and is subject to constant improvement. Nevertheless, there are a number of problems in the treatment of seeds that cannot always be solved satisfactorily. It is therefore desirable to develop methods for protecting the seed and the germinating plant which make the additional application of pesticides during storage, after sowing or after the plants have emerged superfluous or at least significantly reduced. It is also desirable to optimize the amount of active ingredient used so that the seed and the germinating plant are protected as best as possible from infestation by animal pests, but without damaging the plant itself with the active ingredient used. In particular, procedures for Treatment of seeds also include the intrinsic insecticidal or nematicidal properties of pest-resistant or -tolerant transgenic plants in order to achieve optimal protection of the seed and also the germinating plant with a minimum of pesticides.

The present invention therefore also relates in particular to a method for protecting seed and germinating plants from infestation by pests by treating the seed with one of the compounds of the formula (I). The method according to the invention for protecting seed and germinating plants from infestation by pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and a mixture component. It further also includes a method in which the seed is treated at different times with a compound of formula (I) and a mixture component.

The invention also relates to the use of the compounds of formula (I) for the treatment of seed to protect the seed and the plant resulting therefrom from animal pests.

The invention also relates to seed which has been treated with a compound of the formula (I) according to the invention for protection against animal pests. The invention also relates to seed which has been treated at the same time with a compound of formula (I) and a mixture component. The invention further relates to seed which has been treated at different times with a compound of formula (I) and a mixture component. In the case of seed which has been treated at different times with a compound of the formula (I) and a mixture component, the individual substances can be present in different layers on the seed. The layers which contain a compound of the formula (I) and mixture components can optionally be separated by an intermediate layer. The invention also relates to seed in which a compound of formula (I) and a mixture component are applied as part of a coating or as a further layer or further layers in addition to a coating.

The invention also relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.

One of the advantages encountered when a compound of formula (I) acts systemically is that the treatment of the seed protects not only the seed itself but also the resulting plants from animal pests after emergence. In this way, the immediate treatment of the crop at the time of sowing or shortly thereafter can be omitted.

A further advantage can be seen in the fact that treating the seed with a compound of the formula (I) can promote germination and emergence of the treated seed. It is also to be regarded as advantageous that compounds of the formula (I) can also be used in particular in the case of transgenic seed.

Compounds of formula (I) can also be used in combination with compositions or compounds of signaling technology, resulting in better colonization with symbionts, such as rhizobia, mycorrhiza and/or endophytic bacteria or fungi, and/or optimized nitrogen fixation .

The compounds of the formula (I) are suitable for protecting seed of any plant variety used in agriculture, in greenhouses, in forests or in horticulture. In particular, these are seeds from cereals (e.g. wheat, barley, rye, millet and oats), corn, cotton, soybeans, rice, potatoes, sunflowers, coffee, tobacco, canola, rapeseed, beet (e.g Sugar beet and fodder beet), peanut, vegetables (e.g. tomato, cucumber, bean, cabbage, onion and lettuce), fruit plants, turf and ornamental plants. Of particular importance is the treatment of seed from cereals (such as wheat, barley, rye and oats), corn, soybeans, cotton, canola, oilseed rape, vegetables and rice.

As already mentioned above, the treatment of transgenic seed with a compound of the formula (I) is also of particular importance. This is the seed of plants which generally contain at least one heterologous gene which controls the expression of a polypeptide with, in particular, insecticidal or nematicidal properties. The heterologous genes in transgenic seed can originate from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly useful for treating transgenic seed containing at least one heterologous gene derived from Bacillus sp. originates. It is particularly preferably a heterologous gene which originates from Bacillus thuringiensis.

In the context of the present invention, the compound of the formula (I) is applied to the seed. Preferably, the seed is treated in a state in which it is sufficiently stable that no damage occurs during the treatment. In general, seed treatment can be done at any time between harvest and sowing. Usually seeds are used which have been separated from the plant and freed from cobs, husks, stems, husks, wool or pulp. For example, seed can be used that has been harvested, cleaned and dried to a storable moisture content. Alternatively, seeds can also be used which, after drying, e.g. B. treated with water and then dried again, for example priming. In the case of rice seeds, it is also possible to use seeds that have been soaked, for example in water, to a certain stage of the rice embryo ('pigeon breast stage'), stimulating germination and more uniform emergence.

In general, when treating the seed, care must be taken to ensure that the amount of the compound of the formula (I) and/or other additives applied to the seed is chosen so that the germination of the seed is not impaired or the resulting plant is not damaged. This is particularly important for active ingredients that can have phytotoxic effects when applied in certain quantities.

The compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.

The compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating materials for seed, and also ULV formulations.

These formulations are prepared in a known manner by mixing the compounds of the formula (I) with customary additives, such as customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins and also water.

Dyes which can be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both pigments which are sparingly soluble in water and dyes which are soluble in water can be used here. Examples which may be mentioned are those designated Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.

Suitable wetting agents which can be present in the seed-dressing formulations which can be used according to the invention are all substances which promote wetting and which are customary for the formulation of agrochemical active ingredients. Alkylnaphthalene sulfonates, such as diisopropyl or diisobutylnaphthalene sulfonates, can preferably be used.

Suitable dispersants and/or emulsifiers which can be present in the seed-dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active ingredients. Nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants can preferably be used. Particularly suitable nonionic dispersants are ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are, in particular, lignin sulfonates, polyacrylic acid salts and aryl sulfonate-formaldehyde condensates.

All foam-inhibiting substances customary for the formulation of agrochemical active ingredients can be present as defoamers in the seed-dressing formulations which can be used according to the invention. Silicone defoamers and magnesium stearate can preferably be used. All substances which can be used for such purposes in agrochemical agents can be present as preservatives in the seed dressing formulations which can be used according to the invention. Examples include dichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which can be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical agents. Cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly disperse silicic acid are preferred.

Suitable adhesives which can be present in the dressing formulations which can be used according to the invention are all the usual binders which can be used in dressings. Mention may preferably be made of polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

The gibberellins A1, A3 (=gibberellic acid), A4 and A7 are preferably suitable as gibberellins which can be present in the seed dressing formulations which can be used according to the invention, and gibberellic acid is particularly preferably used. The gibberellins are known (cf. R. Wegler "Chemie der Pflanzenschutz- und Schädlingskampfmitel", Vol. 2, Springer Verlag, 1970, pp. 401-412).

The seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of a very wide variety of seeds. Thus, the concentrates or the preparations obtainable therefrom by diluting with water can be used for dressing grain seeds, such as wheat, barley, rye, oats and triticale, and also corn, rice, rapeseed, peas, beans and cotton seeds , sunflowers, soybeans and turnips or also from vegetable seeds of the most diverse nature. The seed dressing formulations which can be used according to the invention or their diluted application forms can also be used for seed dressing of transgenic plants.

For the treatment of seed with the seed dressing formulations which can be used according to the invention or with the application forms produced therefrom by adding water, all mixing devices which can usually be used for dressing can be considered. In detail, the treatment is carried out in such a way that the seed is placed in a mixer in discontinuous or continuous operation, the desired amount of dressing formulations is added either as such or after prior dilution with water and until the formulation is evenly distributed mixed with the seed. If necessary, a drying process follows.

The application rate of the seed dressing formulations that can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed. The application rates for the compound of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed. animal health

In the field of animal health, i. H. in the field of veterinary medicine, the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites. The term endoparasite includes in particular helminths and protozoa such as coccidia. Ectoparasites are typically and preferably arthropods, particularly insects or acarids.

In the field of veterinary medicine, the compounds of formula (I), which have a favorable toxicity to warm-blooded animals, are useful for controlling parasites occurring in livestock, farm animals, zoo animals, laboratory animals, experimental animals and domestic animals in animal breeding and animal husbandry. They are effective against all or individual developmental stages of the parasites.

Examples of farm animals include mammals such as sheep, goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer and, in particular, cattle and pigs; or poultry such as turkeys, ducks, geese and especially chickens; or fish or crustaceans, e.g. B. in aquaculture, or possibly insects such as bees.

The domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets and in particular dogs, cats, house birds; Reptiles, amphibians or aquarium fish.

According to a specific embodiment, the compounds of formula (I) are administered to mammals.

According to a further specific embodiment, the compounds of formula (I) are administered to birds, namely pet birds or in particular poultry.

The use of the compounds of formula (I) for combating animal parasites is said to reduce or prevent disease, deaths and reduced performance (in meat, milk, wool, skins, eggs, honey and the like) so that animal husbandry is more economical and simpler and a better welfare of the animals can be achieved.

In relation to the field of animal health, the term "control" or "control" as used herein means that the compounds of formula (I) are effective in preventing the occurrence of the relevant parasite in an animal infected with such parasite to a harmless level , is reduced. More specifically, "combat" in the present context means that the compounds of formula (I) kill, prevent the growth of or prevent the proliferation of the parasite in question.

Arthropods include, but are not limited to, from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Bovicola spp., Damalina spp., Felicola spp.; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Wemeckiella spp; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Eipoptena spp., Lucilia spp., Lutzomyia spp. , Melophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.; from the order Siphonapterida, for example Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.; from the order Heteropterida, for example Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp.; and nuisance and hygiene pests from the order Blattarida.

Furthermore, among the arthropods, the following Akari are exemplary, without being limited to them:

From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae such as Argas spp., Omithodorus spp., Otobius spp., from the family Ixodidae such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp ., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (the original genus of multi-host ticks); from the order Mesostigmata, such as Dermanyssus spp., Omithonyssus spp., Pneumonyssus spp., Raillietia spp., Stemostoma spp., Tropilaelaps spp., Varroa spp.; from the order Actinedida (Prostigmata), for example Acarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp., Omithocheyletia spp., Psorergates spp., Trombicula spp.; and from the order of the Acaridida (Astigmata), for example Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp ., Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp.

Examples of parasitic protozoa include, but are not limited to:

Mastigophora (Flagellata), such as:

Metamonada: from the order Diplomonadida, for example Giardia spp., Spironucleus spp. Parabasala: from the order Trichomonadida, for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp.

Euglenozoa: from the order Trypanosomatida, for example Leishmania spp., Trypanosoma spp.

Sarcomastigophora (Rhizopoda) such as Entamoebidae, e.g. Entamoeba spp., Centramoebidae, e.g. Acanthamoeba sp., Euamoebidae, e.g. B. Hartmanella sp.

Alveolata such as Apicomplexa (Sporozoa): e.g. B. Cryptosporidium spp.; from the order Eimeriida, for example Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp.; from the order Adeleida z. B. Hepatozoon spp., Klosiella spp.; from the order Haemosporida z. B. Leucocytozoon spp., Plasmodium spp.; from the order Piroplasmida z. B. Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp.; from the order Vesibuliferida z. B. Balantidium spp., Buxtonella spp.

Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., and also e.g. B. Myxozoa spp.

Helminths pathogenic to humans or animals include, for example, Acanthocephala, Pentastoma and Platyhelminths (e.g. Monogenea, Cestodes and Trematodes).

Exemplary helminths include, but are not limited to:

Monogenea: e.g. B.: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp.;

Cestodes: from the order Pseudophyllidea for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.

From the order Cyclophyllida, for example: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp. , Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma sp.

Trematodes: from the class Digenea for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp ., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Omithobilharzia spp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.

Acanthocephala: from the order Oligacanthorhynchida e.g. Macracanthorhynchus spp., Prosthenorchis spp.; from the order Moniliformida for example: Moniliformis spp.,

For example, from the order Polymorphida: Filicollis spp.; from the order Echinorhynchida, for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.

Pentastoma: from the order Porocephalida, for example Linguatula spp.

In the field of veterinary medicine and animal husbandry, the compounds of formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. Administration can be prophylactic; be metaphylactic or therapeutic.

Thus, one embodiment of the present invention relates to the compounds of formula (I) for use as medicaments.

A further aspect relates to the compounds of the formula (I) for use as an anti-endoparasitic.

A further special aspect relates to the compounds of the formula (I) for use as an anthelmintic, in particular for use as a nematicide, platymelminthicide, acanthocephalicide or pentastomicide.

A further special aspect relates to the compounds of the formula (I) for use as an antiprotozoal.

A further aspect relates to the compounds of formula (I) for use as an antiectoparasitic, in particular an arthropodicide, more particularly an insecticide or an acaricide.

Further aspects of the invention are veterinary formulations comprising an effective amount of at least one compound of formula (I) and at least one of the following: a pharmaceutically acceptable excipient (e.g. solid or liquid diluents), a pharmaceutically acceptable adjuvant (e.g. surfactants), especially one a pharmaceutically acceptable excipient conventionally used in veterinary formulations and/or a pharmaceutically acceptable adjuvant conventionally used in veterinary formulations.

A related aspect of the invention is a method of preparing a veterinary formulation as described herein, comprising the step of admixing at least one compound of Formula (I) with pharmaceutically acceptable excipients and/or auxiliaries, in particular with pharmaceutically acceptable excipients and/or auxiliaries conventionally used in veterinary formulations.

Another special aspect of the invention are veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozoal and arthropodicidal formulations, very particularly selected from the group of nematicidal, platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidal and accaricidal formulations, according to the aspects mentioned, and methods for their production.

Another aspect relates to a method of treating a parasitic infection, particularly an infection by a parasite selected from the group consisting of ectoparasites and endoparasites mentioned herein, by applying an effective amount of a compound of formula (I) to an animal, particularly a non-human animal in need of it.

Another aspect relates to a method of treating a parasitic infection, particularly an infection by a parasite selected from the group consisting of ectoparasites and endoparasites mentioned herein, by applying a veterinary formulation as defined herein to an animal, particularly a non-human animal, which requirement.

Another aspect relates to the use of the compounds of formula (I) in the treatment of a parasitic infection, in particular an infection by a parasite selected from the group consisting of ectoparasites and endoparasites mentioned herein, in an animal, in particular a non-human animal.

In the present animal health or veterinary context, the term "treatment" includes prophylactic, metaphylactic and therapeutic treatment.

In a specific embodiment, mixtures of at least one compound of the formula (I) with other active ingredients, in particular with endo- and ectoparasiticides, are hereby provided for the veterinary field.

In the field of animal health, "mixture" not only means that two (or more) different active ingredients are formulated in a common formulation and thus applied together, but also refers to products that comprise separate formulations for each active ingredient. Accordingly, when more than two active ingredients are to be employed, all of the active ingredients can be formulated in a common formulation, or all of the active ingredients can be formulated in separate formulations; mixed forms are also conceivable, in which some of the active ingredients are formulated together and some of the active ingredients are formulated separately. Separate formulations permit separate or sequential application of the active ingredients in question. The active ingredients specified here with their "Common Name" are known and are described, for example, in the "Pesticide Manual" (see above) or can be researched on the Internet (eg http://www.alan-wood.net/pesticides).

Exemplary active ingredients from the group of ectoparasiticides as mixing partners include, without this being intended to constitute a restriction, the insecticides and acaricides listed in detail above. Other useful active ingredients are listed below according to the above classification based on the current IRAC Mode of Action Classification Scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GAB A-gated chloride channel blockers; (3) sodium channel modulators; (4) competitive modulators of the nicotinic acetylcholine receptor (nAChR); (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) allosteric modulators of the glutamate-gated chloride channel (GluCl); (7) juvenile hormone mimetics; (8) various non-specific (multi-site) inhibitors; (9) modulators of chordotonal organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors; (13) decouplers of oxidative phosphorylation by disrupting the proton gradient; (14) nicotinic acetylcholine receptor channel blockers; (15) inhibitors of chitin biosynthesis, type 0; (16) inhibitors of chitin biosynthesis, type 1; (17) moult disruptor (particularly in Diptera, i.e., flies); (18) ecdysone receptor agonists; (19) octopamine receptor agonists; (21) mitochondrial complex I electron transport inhibitors; (25) mitochondrial complex II electron transport inhibitors; (20) mitochondrial complex III electron transport inhibitors; (22) voltage-gated sodium channel blockers; (23) inhibitors of acetyl-CoA carboxylase; (28) ryanodine receptor modulators; (30) allosteric modulators of the GABA-dependent chloride channel.

Drugs with unknown or non-specific mechanisms of action, e.g. fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazon, gossyplur, flutenzin, bromopropylate, cryolite;

Compounds from other classes, e.g. butacarb, dimetilan, cloethocarb, phosphocarb, pirimiphos(- ethyl), parathion(-ethyl), methacrifos, isopropyl-o-salicylate, trichlorfon, tigolaner, sulprofos, propaphos, sebufos, pyridathion, prothoate, Diclofenthion, Demeton-S-methylsulfone, Isazofos, Cyanofenphos, Dialifos, Carbophenothion, Autathiofos, Aromfenvinfos(-methyl), Azinphos(-ethyl), Chlorpyrifos(- ethyl), Fosmethilan, lodofenphos, Dioxabenzofos, Formothion, Fonofos, Flupyrazofos, Fensulfothion, Etrimfos;

organochlorine compounds, e.g. B. camphechlor, lindane, heptachlor; or phenylpyrazoles, e.g. B. acetoprol, pyrafluprole, pyriprole, vaniliprole, sisapronil; or isoxazolines, e.g. B. sarolaner, afoxolaner, lotilaner, fluralaner; pyrethroids, e.g. B. (cis-, trans-)Metofluthrin, Profluthrin, Flufenprox, Flubrocythrinat, Fubfenprox, Fenfluthrin, Protrifenbut, Pyresmethrin, RU15525, Terallethrin, cis-Resmethrin, Heptafluthrin, Bioethanomethrin, Biopermethrin, Fenpyrithrin, cis-Cypermethrin, cis -permethrin, clocythrin, cyhalothrin (lambda-), chlovaporthrin, or halogenated hydrocarbon compounds (HCHs),

neonicotinoids, e.g. B. Nithiazine

dicloromezotiaz, triflumezopyrim macrocyclic lactones e.g. nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; milbemycin oxime

triprene, epofenonane, diofenolane;

Biologicals, hormones or pheromones, for example natural products, e.g. thuringiensin, codlemon or neem components

dinitrophenols, e.g. B. Dinocap, Dinobuton, Binapacryl;

benzoylureas, e.g. e.g. fluazuron, penfluron,

amidine derivatives, e.g. chlormebuform, cymiazole, demiditraz

Beehive varroa acaricides, for example organic acids, e.g., formic acid, oxalic acid.

Exemplary endoparasiticidal active ingredients, as admixture partners, include, but are not limited to, anthelmintic active ingredients and antiprotozoal active ingredients.

Anthelmintic agents include, but are not limited to, the following nematicidal, trematicidal and/or cestocidal agents: from the macrocyclic lactone class, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, ivermectin, emamectin, milbemycin; from the class of benzimidazoles and probenzimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimine, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole, flubendazole; from the class of depsipeptides, preferably cyclic depsipeptides, in particular 24-membered cyclic depsipeptides, for example: emodepside, PF1022A; from the class of tetrahydropyrimidines, for example: morantel, pyrantel, oxantel; from the class of imidazothiazoles, for example: butamisole, levamisole, tetramisole; from the class of aminophenylamidines, for example: amidantel, deacylated amidantel (dAMD), tribebendimidine; from the class of aminoacetonitriles, for example: monepantel; from the class of paraherquamides, for example: paraherquamide, derquantel; from the class of the salicylanilides, for example: tribromosalan, bromoxanide, brotianide, clioxanide, closantel, niclosamide, oxyclozanide, rafoxanide; from the class of substituted phenols, for example: nitroxinil, bithionol, disophenol, hexachlorophene, niclofolan, meniclopholan; from the class of organophosphates, for example: trichlorfon, naphthalofos, dichlorvos/DDVP, crufomat, coumaphos, haloxon; from the class of piperazinones/quinolines, for example: praziquantel, epsiprantel; from the piperazine class, for example: piperazine, hydroxyzine; from the class of tetracyclines, for example: tetracycline, chlorotetracycline, doxycycline, oxytetracycline, rolitetracycline; from various other classes for example: bunamidine, niridazole, resorantel, omphalotin, oltipraz, nitroscanate, nitroxynil, oxamniquine, mirasan, miracil, lucanthone, hycanthone, hetolin, emetine, diethylcarbamazine, dichlorophene, diamfenetide, clonazepam, bephenium, amoscanate , Clorsulon.

Antiprotozoal agents including but not limited to the following agents: from the triazine class, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the polylether ionophore class, for example: monensin, salinomycin, maduramicin, narasin; from the class of macrocyclic lactones, for example: milbemycin, erythromycin; from the class of quinolones, for example: enrofloxacin, pradofloxacin; from the class of quinines, for example: chloroquine; from the class of pyrimidines, for example: pyrimethamine; from the class of sulfonamides, for example: sulfaquinoxaline, trimethoprim, sulfaclozine; from the class of thiamines, for example: amprolium; from the class of lincosamides, for example: clindamycin; from the class of carbanilides, for example: imidocarb; from the class of the nitrofurans, for example: nifurtimox; from the class of the quinazolinone alkaloids, for example: halofuginone; from various other classes for example: oxamniquin, paromomycin; from the class of vaccines or antigens from microorganisms, for example: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimeria necatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Dictyocaulus viviparus.

If they are capable of doing so because of their functional groups, all of the mixing partners mentioned can also form salts with suitable bases or acids.

vector control

The compounds of the formula (I) can also be used in vector control. A vector within the meaning of the present invention is an arthropod, in particular an insect or arachnid, which is capable of pathogens such as. B. viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to transfer to a host. The pathogens can be transmitted to a host either mechanically (e.g. trachoma by non-stinging flies) or after injection (e.g. malaria parasites by mosquitoes) into a host.

Examples of vectors and the diseases or pathogens they transmit are:

1) mosquitoes

- Anopheles: malaria, filariasis;

- Culex: Japanese encephalitis, other viral diseases, filariasis, transmission from other worms;

- Aedes: yellow fever, dengue fever, other viral diseases, filariasis;

- Simulations: transmission of worms, especially Onchocerca volvulus;

- Psychodidae: transmission of leishmaniasis

2) lice: skin infections, epidemic typhus; 3) fleas: plague, endemic typhus, tapeworms;

4) Flies: sleeping sickness (trypanosomiasis); cholera, other bacterial diseases;

5) mites: acariose, epidemic typhus, rickettsipox, tularemia, Saint-Louis encephalitis, tick-borne encephalitis (FSME), Crimean-Congo hemorrhagic fever, Lyme disease;

6) Ticks: Lyme disease such as Borrelia bungdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), babesia (Babesia canis canis), Ehrlichiosis.

Examples of vectors for the purposes of the present invention are insects, for example aphids, flies, leafhoppers or thrips, which can transmit plant viruses to plants. Other vectors that can transmit plant viruses are spider mites, lice and beetles.

Further examples of vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, e.g. B. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, Psychodids such as Phlebotomus, Lutzomyia, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and/or humans.

Vector control is also possible when the compounds of formula (I) are resistance-breaking.

Compounds of formula (I) are suitable for use in the prevention of diseases and/or pathogens which are transmitted by vectors. Thus a further aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. B. in agriculture, in horticulture, in gardens and leisure facilities as well as in the protection of stored products and materials.

Protection of technical materials

The compounds of formula (I) are suitable for protecting technical materials against infestation or destruction by insects, e.g. B. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.

In the present context, technical materials are to be understood as meaning non-living materials, such as preferably plastics, adhesives, glues, paper and cardboard, leather, wood, wood processing products and paints. Application of the invention to the protection of wood is particularly preferred.

In a further embodiment, the compounds of the formula (I) are used together with at least one further insecticide and/or at least one fungicide.

In a further embodiment, the compounds of formula (I) are present as a ready-to-use pest control agent, ie they can be applied to the appropriate material is applied. As further insecticides or fungicides, those mentioned above are particularly suitable.

Surprisingly, it has also been found that the compounds of the formula (I) can be used to protect objects, in particular ship hulls, sieves, nets, structures, quays and signaling systems, which come into contact with seawater or brackish water, from fouling. Likewise, the compounds of the formula (I) can be used alone or in combination with other active ingredients as antifouling agents.

Combating animal pests in the hygiene sector

The compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector. In particular, the invention can be used in household, hygiene and stored product protection, especially for combating insects, arachnids, ticks and mites that occur in closed rooms such as apartments, factory buildings, offices, vehicle cabins, animal breeding facilities. To combat animal pests, the compounds of the formula (I) are used alone or in combination with other active ingredients and/or auxiliaries. They are preferably used in household insecticide products. The compounds of formula (I) are active against sensitive and resistant species and against all stages of development.

These pests include, for example, pests from the class Arachnida, from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta, the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.

The application takes place, for example, in aerosols, non-pressurized sprays, e.g. B. pump and atomizer sprays, smoke machines, foggers, foams, gels, vaporizer products with vaporizer plates made of cellulose or plastic, liquid vaporizers, gel and membrane vaporizers, propeller-driven vaporizers, energyless or passive vaporization systems, moth paper, moth bags and moth gels, as granules or dust, in scatter baits or bait stations.

The following production and use examples illustrate the invention without restricting it.

Manufacturing examples

Synthesis of N-(4,4-difluorocyclohexyl)-3-[4-({[(2-isopropylphenyl)carbamothioyl]hydrazono}methyl)phenyl]-1-methyl-1H-1,2,4-triazol- 5-carboxamide (1-06) and N-(4,4-difluorocyclohexyl)-3-[4-({[3-(2-isopropylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]hydrazono }methyl)phenyl]-l-methyl-lH-l,2,4-triazole-5-carboxamide (Example 1-11) 1st stage:

217 mg of 4,4-difluorocyclohexylamine hydrochloride (1.27 mmol, 1.4 eq.) are placed in a 20 ml flat-bottom vial, dissolved in 6 ml of dry toluene and the vial is sealed. The solution is degassed with argon for 5 minutes. With slight cooling (cold water, approx. 15° C.), 0.64 ml of trimethylaluminum (2M in toluene, 1.24 mmol, 1.4 eq.) is added dropwise using a syringe (slight evolution of gas, slightly exothermic reaction). After 10 minutes, 200 mg of methyl 3-bromo-1-methyl-1H-1,2,4-triazole-5-carboxylate (0.91 mmol, 1.0 eq) dissolved in 6 ml of dry tetrahydrofuran are quickly added using a syringe and place the reaction vessel in an aluminum block preheated to 80 °C. After 3 h, LC/MS shows complete conversion. The reaction was cooled to room temperature and poured into a 60 mL Na/K tartrate 10% sol/EtOAc (1:1) mixture. Stirring is continued until phase separation is complete. The phases are separated and the aqueous phase is extracted with EtOAc (2×30 ml). The combined organic phases are washed with water and NaCl solution (30 ml each), dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by means of flash chromatography (Combi-Flash, 15 g SiO2, gradient c-Hex/EtOAc=100:0→0:100). 210 mg of 3-bromo-N-(4,4-difluorocyclohexyl)-1-methyl-1H-1,2,4-triazole-5-carboxamide are obtained as a white solid (96% purity, 68% yield)

2nd stage:

275 mg (0.85 mmol, 1.0 eq.) 3-bromo-N-(4,4-difluorocyclohexyl)-l-methyl-lH-l,2,4-triazole-5-carboxamide, 153 mg (1.02 mmol, 1.2 eq.) 4-Formylphenylboronic acid and 554 mg (1.70 mmol, 2.0 eq.) cesium carbonate are placed in a microwave vessel (2-5 ml) and dissolved in 4 ml dioxane/water (3:1). The solution is degassed with argon for 5 minutes. 42 mg (0.051 mmol, 6 mol%) l,l'-bis(diphenylphosphinoferrocenepalladium(II) dichloride dichloromethane complex are added, the microwave vessel is sealed and placed in an aluminum block preheated to 90° C. After 3 h, a LC/MS complete conversion The reaction was cooled to room temperature and poured into 60 mL of EtOAc/NFLCl (1:1) The phases were separated and the aqueous extracted with EtOAc (2 x 30 mL). organic phases are washed with water and NaCl solution (30 ml each), dried over sodium sulfate, filtered and concentrated in vacuo Purified by flash chromatography (Combi-Flash, 15 g SiCh, gradient c-Hex:EtOAc = 100:0^0:100). 240 mg of N-(4,4-difluorocyclohexyl)-3-(4-formylphenyl)-1-methyl-1H-1,2,4-triazole-5-carboxamide are obtained as a white solid (97% purity, 78% yield ).

3rd stage:

240 mg (0.69 mmol, 1.0 eq) N-(4,4-difluorocyclohexyl)-3-(4-formylphenyl)-1-methyl-1H-1,2,4-triazole-5-carboxamide and 144 mg (0.69 mmol , 1.0 eq.) N-(2-isopropylphenyl)hydrazinecarbothioamide (known from WO 2010/062559) are placed in a 50 ml round bottom flask and suspended in 10 ml absolute ethanol. The reaction is stirred at reflux for 3 h. A clear, yellow solution is obtained. LC/MS shows complete conversion. The solution is cooled to room temperature and the solvent removed in vacuo. The residue is taken up in 50 mL EtOAc/water (1:1). Separate the phases and extract the aqueous with EtOAc (2 x 30 mL). The combined organic phases are washed with water and NaCl solution (30 ml each), dried over sodium sulfate, filtered and concentrated in vacuo. 340 mg of N-(4,4-difluorocyclohexyl)-3-[4-({[(2-isopropylphenyl)carbamothioyl]hydrazono}methyl)phenyl]-1-methyl-1H-1,2,4- triazole-5-carboxamide (1-06) as a yellow solid (92% purity, 84% yield) which is reacted without further purification.

4th stage:

330 mg (0.61 mmol, 1.0 eq.) N-(4,4-Difluorocyclohexyl)-3-[4-({[(2-isopropylphenyl)carbamothioyl]hydrazono}methyl)phenyl]-l-methyl-lH- 1,2,4-triazole-5-carboxamide and 201 mg sodium acetate (2.45 mmol, 4.0 eq.) are placed in 20 ml absolute ethanol in a 50 ml round bottom flask. 123 mg (0.74 mmol, 1.2 eq.) ethyl bromoacetate are added and the mixture is stirred under reflux for 6 h. An LC/MS shows complete turnover. It is cooled to room temperature and the batch is poured into 50 ml of water. It is then acidified to pH 3-4 with citric acid and the resulting precipitate is filtered off with suction. The solid is dried and purified by means of flash chromatography (CombiFlash, 15 g SiOi. Gradient c-Hex/EtOAc=100:0^0:100). 210 mg of N-(4,4-difluorocyclohexyl)-3-[4-({[3-(2-isopropylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]hydrazono}methyl)phenyl] are obtained. - 1-methyl-1H-1,2,4-triazole-5-carboxamide (I-11) as a white solid (93% purity, 55% yield).

NMR data of selected examples

The measurements of the ¹ H-NMR spectra were carried out with a Bruker Avance III 400 MHz spectrometer equipped with a 1.7 mm TCI probe head with tetramethylsilane as standard (0.00 ppm) and the measurements were recorded usually from solutions in the solvents CD3CN, CDCL or dg-DMSO. Alternatively, a Bruker Avance III 600 MHz spectrometer equipped with a 5 mm CPNMP probe head or a Bruker Avance NEO 600 MHz spectrometer equipped with a 5 mm TCI probe head was used for the measurements. As a rule, the measurements were carried out at a probe head temperature of 298 K. If other measurement temperatures were used, this will be noted separately.

NMR peak list method

The 'H NMR data of selected examples are reported in the form of 'H NMR packages. For each signal peak, first the 5 value in ppm and then the signal intensity is listed in round brackets. The 5-value signal intensity number pairs from different signal peaks are listed separated by semicolons.

The peak list of an example therefore has the form:

5i (intensityi); 02 (intensity2); ; 5i (intensityi); ; 5 _n (intensity)

The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown.

To calibrate the chemical shift of 'H NMR spectra, we use tetramethylsilane and/or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. The tetramethylsilane peak can therefore appear in NMR peak lists, but it does not have to.

The lists of ¹ H NMR Pcaks are equivalent to the classical ¹ HN MR printouts and thus usually contain all peaks that are also listed in a classical NMR interpretation. In addition, like classic ¹ HN MR prints, they can show solvent signals, signals from stereoisomers of the target compounds, which are also the subject of the invention, and/or peaks from impurities.

¹ HN MR solvent signalc. the tetramethylsilane signal and the water signal in the respective solvent are excluded from the relative intensity calibration because the intensity values given for them can be very high.

The peaks of stereoisomers of the target compounds and/or peaks of impurities usually have on average a lower intensity than the peaks of the compounds according to the invention (for example with a purity of >90%).

Such stereoisomers and/or impurities can be typical of the particular production process. Their peaks can thus help to identify the reproduction of our manufacturing process using 'by-product fingerprints'.

An expert who calculates the peaks of the target compounds using known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can isolate the peaks of the target compounds as required, with additional intensity filters being used if necessary. This isolation would be similar to the peak picking involved in classical ¹ H NMR interpretation.

The solvent used can be read from the JCAMP file with the parameter "solvent", the measuring frequency of the spectrometer with "observe frequency" and the spectrometer model with "spectrometer/data system".

Further details on NMR data description with peak lists can be found in: “Citation of NMR Peaklist Data within Patent Applications” in Research Disclosure Database Number 564025.

Tabelle 1

Anwendungsbeispiele The compounds of the formula (I) listed in Table 1 can be obtained analogously to the examples and according to the preparation processes described above:

Table 1

Application examples

Boophilus microplus injection test

Solvent: dimethyl sulfoxide

To produce an appropriate preparation of active ingredient, 10 mg of active ingredient are mixed with 0.5 ml of solvent and the concentrate is diluted with solvent to the desired concentration.

1 JJ.1 of the active substance solution is injected into the abdomen of 5 engorged, adult, female cattle ticks (Boophilus microplus). The ticks are transferred to bowls and kept in an air-conditioned room.

The effect is checked after 7 days on the laying of fertile eggs. Eggs whose fertility is not externally visible are kept in the climate cabinet until the larvae hatch after about 42 days. An activity of 100% means that none of the ticks laid fertile eggs, 0% means that all eggs are fertile.

In this test, for example, the following compounds from the preparation examples show an activity of 80% at an application rate of 20 pg/tick: 1-01.

Ctenocephalides felis - in-vitro contact tests with adult cat fleas

To coat the test tubes, first 9 mg of active substance are dissolved in 1 ml of acetone AR and then diluted to the desired concentration with acetone AR. 250 μl of the solution are distributed homogeneously on the inner walls and the bottom of a 25 ml glass tube by turning and tilting on a rotary shaker (2 h rocking rotation at 30 rpm). With a 900 ppm active ingredient solution and an internal surface area of 44.7 cm ² , a dose per unit area of 5 pg/cm ² is achieved with homogeneous distribution.

After the solvent has evaporated, the vials are filled with 5-10 adult cat fleas (Ctenocephalides felis), sealed with a perforated plastic lid and incubated lying down at room temperature and ambient humidity. After 48 hours, the effectiveness is determined in comparison to the untreated control. To do this, the jars are placed upright and the fleas are knocked on the bottom of the jar. Fleas that remain motionless on the ground or move in an uncoordinated manner are considered dead or battered.

A substance shows a good activity against Ctenocephalides felis if at least 80% activity was achieved in this test at an application rate of 5 pg/cm ² . 100% effectiveness means that all fleas were infected or dead. 0% effectiveness means no fleas were harmed. In this test, for example, the following compounds from the preparation examples show an activity of 80% at an application rate of 5 pg/cm ² (=500 g/ha): 1-01, 1-02, 1-03, 1-04.

Ctenocephalides felis - oral test

Solvent: dimethyl sulfoxide

In order to produce an appropriate active substance preparation, 10 mg of active substance are mixed with 0.5 ml of dimethyl sulfoxide. The desired concentration is obtained by diluting with citrated bovine blood.

About 20 fasting adult cat fleas (Ctenocephalides felis) are placed in a chamber which is closed with gauze at the top and bottom. A metal cylinder is placed on the chamber, the underside of which is sealed with Parafdm. The cylinder contains the blood-active substance preparation, which can be absorbed by the fleas through the parafilm membrane. The cylinder is warmed to 37°C while the fly chamber is kept at room temperature.

After 2 days, the destruction in % is determined in comparison to the untreated control. 100% means that all fleas have been killed; 0% means none of the fleas have been killed.

In this test, for example, the following compounds from the preparation examples show an activity of 100% at an application rate of 100 ppm: 1-02.

Diabrotica balteata - spray test

Solvent: 78 parts by weight acetone

1.5 parts by weight dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To prepare an appropriate preparation of active compound, 1 part by weight of active compound is dissolved in the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with water containing emulsifier.

Preswollen wheat grains (Triticum aestivum) are incubated in a multiwell plate filled with agar and a little water for one day (5 seeds per well). The germinated wheat grains are sprayed with an active ingredient preparation of the desired concentration. Each cavity is then infected with 10-20 Diabrotica balteata beetle larvae.

After 7 days, the effect is determined in %. 100% means that all wheat plants grew as in the untreated, uninfected control; 0% means that no wheat plant has grown. In this test z. B. the following compounds of the preparation examples effect of 100% at an application rate of 100 g / ha (= 32 pg / cavity): 1-01, 1-02, 1-03, 1-04, 1-06, 1-07 , 1-08, 1-09, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1 -20, 1-24, 1-26, 1-27, 1-28, 1-30, 1-31, 1-32, 1-33, 1-34, 1-35, 1-36, 1-37 , 1-38, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45, 1-46.

Nezara viridula spray test

Solvent: 78.0 parts by weight acetone

1.5 parts by weight dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To prepare an appropriate preparation of active ingredient, 1 part by weight of active ingredient is dissolved in the specified parts by weight of solvent and precipitated with water containing an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with water containing emulsifier.

Barley plants (Hordeum vulgare) are sprayed with a preparation of active compound of the desired concentration and infected with larvae of the green rice bug (Nezara viridula).

After 4 days, the effect is determined in %. 100% means that all rice bugs have been killed; 0% means no rice bugs have been killed.

In this test z. B. the following compounds of the preparation examples effect of 100% at an application rate of 500 g / ha: 1-32, 1-33, 1-37, 1-45.

In this test z. B. the following compounds of the preparation examples effect of 90% at an application rate of 500 g / ha: 1-43.

Spodoptera frugiperda - spray test

Solvent: 78.0 parts by weight acetone

1.5 parts by weight dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To prepare an appropriate preparation of active compound, 1 part by weight of active compound is dissolved in the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with water containing emulsifier.

Corn leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are populated with caterpillars of the armyworm (Spodoptera frugiperda). After 7 days, the effect is determined in %. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.

In this test z. B. the following compounds of the preparation examples effect of 100% at an application rate of 100 g / ha: 1-01, 1-02, 1-03, 1-04, 1-05, 1-06, 1-07, 1- 09, 1-11, 1-12, 1-13, 1-14, 1-16, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33, 1-34, 1-35, 1-36, 1-

37, 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45, 1-46.

In this test z. B. the following compounds of the preparation examples Effect of 83% at an application rate of 100 g/ha: 1-10.

Claims

compound of formula (I)

wherein A is N or CR ^A ; stands by R ^A is H, halogen, cyano, nitro, SF ₅ , NR ^{d Re} , OR ^a , S(O) _n R ^a or SO ₂ NR ^b R ^c ; or for Ci-Cg-alkyl, C -Cg-alkcnyl. C -Cg alkynyl or CACv cycloalkyl. each of which can be unsubstituted or substituted once to 13 times with halogen and/or optionally with 1 to 3 R ^f ; V is -C(Q ¹ )NR ^V1 R ^V2 ; stands by R ^V1 for Ci-C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₇ cycloalkyl, C ₅ -C ₇ cycloalkenyl or saturated C ₃ -C ₇ ^{-heterocyclyl} , all of which can be unsubstituted or optionally substituted once to 13 times with halogen and/or with 1 to 2 Rh; R ^V2 for H; or for Ci-Cg-alkyl, C ₂ -Cg-alkenyl, C ₂ -C6-alkynyl, Ci-Cg-alkoxy, C ₃ - C ₇ -cycloalkyl or Cs-C ₇ -cycloalkenyl, all unsubstituted or singly up to 13 -fold substituted with halogen and/or optionally with 1 to 2 R ^g ; or R ^V1 and R ^V2 together with the nitrogen atom to which they are attached stand for a saturated, partially saturated or aromatic heterocycle having 3 to 7 ring atoms which is optionally interrupted by further heteroatoms and/or by one or two C=O groups and which ^is unsubstituted in each case or can be substituted once to seven times by halogen and/or optionally by 1 to 2 Rh; ^R1 is H; or for Ci-Cg-alkyl, C ₂ -Cg-alkenyl, C ₂ -Cg-alkynyl, C ₃ -C ₇ -cycloalkyl, Ci- Cg-alkylcarbonyl, C ₃ -C ₇ -cycloalkylcarbonyl, Ci-Cg-alkoxycarbonyl, C ₃ -C ₇ -cycloalkoxyylcarbonyl, Ci-Cg -alkylsulfonyl or C ₃ -C ₇ -cycloalkylsulfonyl, all of which may be unsubstituted in each case, or mono- to 13-fold with halogen and/or optionally with 1 to 2 R ^h may be substituted; R ² represents the substructure of the general formula -XYZ; stands by X is phenyl or a 5- or 6-membered heteroaromatic ring each unsubstituted or substituted by 1 to 3 R ^x ; each is included R ^x are independently halogen, cyano, nitro, C (Q ¹ )R ^a . C(O)OR ^a , C(Q ¹ )NR ^b R ^c , NR ^{d Re} , OR ^a , S(O) _n R ^a or SO ₂ NR ^b R ^c ; or for CI-C ₆ -A1- kyl, C ₂ -Cg -alkenyl, C ₂ -Cg-alkynyl or C-CS-cycloalkyl. all in each case unsubstituted or substituted once to 13 times by halogen and/or optionally by 1 to 3 R ^f ; Y for - CR ^Y1 =N- where N is bonded to Z, or for -NR ^Y2 -C(=Q ^Y )-, where C is bonded to Z; each is included R ^Y1 and R ^Y2 for H; or for Ci-Cg-alkyl, C ₂ -Cg-alkenyl, C ₂ -Cg-alkynyl or C3-C?-cycloalkyl, each unsubstituted or substituted by 1 to 7 R ^Y11 ; each is included R ^Y11 independently for halogen, cyano, Ci-C4-alkyl, C3-Cg-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or C1-C4-haloalkoxy; Q ^{Y is} O or S; Z for the fragments of the general formula (A1), (A2) or (A3);

where # is the connecting point to Y and where each stands T for O or S; R ^Z1 independently represent a 5- to 10-membered aromatic or heteroaromatic ring or a bicyclic ring system, each unsubstituted or substituted by 1 to 4 R ^Z11 ; each is included R ^Z11 independently for halogen, cyano, nitro, SF5, C(Q')R ^a . C(O)OR ^a , C(Q ¹ )NR ^b R ^c , NR ^{d Re} , OR ^a , S(O) _n R ^a or SO ₂ NR ^b R ^c ; or for Ci-Cg-alkyl, C ₂ -C6-alkenyl, C ₂ -Cg-alkynyl or C ₃ -C ₇ -cycloalkyl, all unsubstituted or substituted by 1 to 5 R ^zla ; or for phenyl or a 5- or 6-membered heteroaromatic ring each unsubstituted or substituted with 1 to 3 R ^zla ; or two adjacent R ^Z11 together form a linear C -C> -alkylcn group which is unsubstituted or substituted with 1 to 6 R ^z1a . where, independently of one another, 1 CH ₂ unit can be replaced by carbonyl and 1 to 2 CH ₂ units by O, S, NH or N(CH ₃ ); each is included R ^zla for halogen, cyano, Ci-C-ralkyl, Ci-C-ralkoxy, Ci-C-rthioalkyl, Ci-C4-haloalkyl or Cj-C -haloalkoxy: R ^Z2 , R ^Z2a and R ^Z3 independently represent H; or for C(O)R ^a , C(O)OR ^a , C(O)NR ^b R ^c , S(O) _n R ^a ; or for C 1 -C 6 -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C 8 -alkynyl or C ₃ -C ₇ -cycloalkyl, all of which are unsubstituted or substituted by 1 to 5 R ^Z21 ; or phenyl, benzyl or a 5- or 6-membered heteroaromatic ring, each unsubstituted or substituted by 1 to 4 R ^Z21 ; each is included R ^Z21 independently for halogen, cyano, nitro, SF5, C(Q')R ^a . C(O)ORa ^{, C} (Q') ^NRb Rc . NR ^d R ^e , OR ^a , S(O) _n R ^a or SO ₂ NR ^b R ^c ; or for Ci-Cg-alkyl, Ci-Cg-haloalkyl, C ₂ -C6-alkenyl, -Ce-alkynyl or C ₃ -C ₇ - cycloalkyl; or R ^Z2 and R ^Z3 together with the TCN moiety form a 5- to 7-membered ring; the R ^Z2 -R ^Z3 ring members consist of carbon atoms and optionally 1 oxygen or sulfur or nitrogen atom; the heteroatom is not directly bonded to T; up to 2 carbon atom ring members can independently consist of C(=O) and C(=S) and the sulfur atom ring member can consist of S, S(O) or S(O) ₂ ; this R ^{Z2 -R Z3} unit is unsubstituted or substituted by 1 to 5 R ^Z21 ; each is included R ^Z21 independently for halogen, hydroxy, cyano, Ci-Cg -alkyl, C ₃ - Cg-Cycloalkyl, Ci-Cg-Haloalkyl, Cj-C -Alkcnyl. Ci-Cg-alkoxy or Ci-Cg-haloalkoxy; or for spirocyclically bonded heterocyclyl having 2 to 7 ring atoms, where 1 to 2 oxygen atoms are present as heteroatoms; or R ^Z2a and a second R ^Z2a together with the NCN moiety form a 5- to 7-membered ring; the R ^Z2a -R ^Z2a ring members consist of carbon atoms and up to 2 heteroatoms, which can be selected independently from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms; up to 2 carbon atom ring members can independently consist of C(=O) and C(=S) and the sulfur atom ring member can consist of S, S(O) or S(O) ₂ ; where this R ^Z2 -R ^Z3 unit is unsubstituted or substituted by 1 to 5 R ^Z21 ; each is included R ^a independently for Ci-Cg-alkyl, GG-cycloalkyl. C2-Cg-alkenyl or C2-Cg-alkynyl, all of which can be unsubstituted or substituted once to 13 times with halogen and/or optionally with 1 to 3 R ^f ; or phenyl unsubstituted or substituted by 1 to 5 R ^g ; R ^b and R ^c are independently H; or for Ci-Cg-alkyl, C ₃ -G, -cycloalkyl. C2-Cg-alkenyl or C2-Cg-alkynyl, each of which can be unsubstituted or substituted once to 13 times with halogen and/or optionally with 1 to 3 R ^f ; or R ^b and R ^c together form a 3- to 7-membered ring; R ^d and R ^e are independently H, C(Q')R ^a . C(O) ^ORa ; or for Ci-Cg-alkyl, Cs-Cg-cycloalkyl, C2-Cg-alkenyl or C2-Cg-alkynyl, all of which may be unsubstituted in each case, or mono- to 13-fold with halogen and / or optionally with 1 bis 3 R ^f may be substituted; or phenyl unsubstituted or substituted by 1 to 5 R ^g ; or R ^d and R ^e together form a 3- to 7-membered ring; R ^f are independently halogen, cyano, nitro, GG-cycloalkyl. Ci-C4 alkoxy, Ci-C4 haloalkoxy, Ci-C4 alkylthio, Ci-C4 haloalkylthio, Ci-C4 alkylsulfmyl, C1-C4 haloalkylsulfmyl, Ci-C4 alkylsulfonyl, Ci-C4 haloalkylsulfonyl, Ci- C4-alkylcarbonyl or C1-C4-alkoxycarbonyl; or phenyl or a 5- or 6-membered heteroaromatic ring each unsubstituted or substituted with 1 to 7 R ^g ; R ^g independently for halogen, cyano, nitro, Ci-C4-alkyl, GG-cycloalkyl. Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfmyl, Ci-C4-haloalkylsulfmyl, Ci-C4-alkylsulfonyl, Ci- C4-haloalkylsulfonyl, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl; R ^h is independently halogen, cyano, nitro, hydroxy, SGOSCfR ³ . SC> ^{2NRb Rc} , N(Rd )(Re ), ^C (Q ^' ) ^{NRb Rc} . N^jCCQ^R ³ , C(O)R ^a , OC(O)R ^a or =Q ² ; or for C1-C4- _{AI kyl} , Ci-C4- _alkoxy , Ci-C4- _alkylthio , Ci-C4-alkylsulphinyl, Ci-C4-alkylsulfonyl, _C3 -Cg-cycloalkyl, spirocyclically bonded C2-Cg -cycloalkyl, spirocyclically bound heterocyclyl with 3 to 7 ring atoms, GG-cycloalkylthio. GG-cycloalkoxy. GG-cycloalkylsulfmyl or GG-cycloalkylsilfonyl. each of which can be unsubstituted or substituted once to 13 times with halogen and/or optionally with 1 to 2 R ^g could be; or phenyl or a 4- to 7-membered saturated, partially saturated or aromatic heterocycle having 1 to 4 heteroatoms, all of which may be unsubstituted or substituted once to 5 times by halogen and/or optionally by 1 to 2 R ^g be able; Q ¹ are independently O, S, NOR ^a or NCN; Q ² are independently O or N0R ^a ; and n is independently 0, 1 or 2. A compound according to claim 1, wherein A is N or CR ^A ; stands by ^RA for H, halogen, cyano or SF5; or for C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 8 -alkynyl or C ₃ -C 8 -cycloalkyl, all of which can be unsubstituted in each case, or mono- to quintuple with halogen and/or optionally with an R ^f may be substituted; V is -C(Q ¹ )NR ^V1 R ^V2 ; stands by R ^V1 for Ci-Cg-alkyl, C ₂ -Cg-alkenyl, C ₂ -Cg-alkynyl, C ₃ -C ₇ -cycloalkyl, C ₅ -C ₇ -cycloalkenyl or a saturated C ₃ -C ₇ -heterocyclyl, the all of which can be unsubstituted in each case, or can ^optionally be substituted once to five times with halogen and/or with 1 to 2 Rh; R ^V2 for H; or for Ci-Cg-alkyl, C ₂ -Cg-alkenyl, C ₂ -Cg-alkynyl, Ci-Cg-alkoxy, C ₃ -C ₇ -cycloalkyl or Cs-C ₇ -cycloalkenyl all unsubstituted or simply bis substituted five times with halogen and/or optionally with 1 to 2 R ^g ; or R ^V1 and R ^V2 together with the nitrogen atom to which they are attached represent a heterocycle from the series U-01 to U-06

U-01 and U-02 U-03 U-04 U-05 U-06 where all U-01 to U-06 can each be unsubstituted or optionally substituted once to 5 times with halogen and/or optionally with 1 to 2 ^{rows R1} for H; for C1-C4 alkyl. C2-C4-alkenyl, C2-C6-alkynyl or Cs-C6-cycloalkyl, all of which may be ^{unsubstituted} or substituted once to five times with halogen and/or optionally with Ibis 2 Rh; R ² represents the substructure of the general formula -XYZ; stands by X is phenyl, pyridyl, pyrimidyl, pyridazinyl or thienyl, each unsubstituted or substituted by 1 to 3 R ^x ; stands by R ^x are independently halogen, cyano, nitro, Q^R ³ , C(O)OR ^a ; or for C1-C4-alkyl, C2-C4-alkenyl, C-C4-alkoxy, C2-Cg-alkynyl or C-Cg-cycloalkyl. all each unsubstituted or substituted with 1 to 3 R ^f ; Y for - CR ^Y1 =N- where N is bonded to Z, or for -NR ^Y2 -C(=Q ^Y )-, where C is bonded to Z; each is included R ^Y1 and R ^Y2 for H; or for C 1 -C 4 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 4 -alkynyl or C 3 -C 4 -cycloalkyl, all of which are unsubstituted or substituted by 1 to 3 R ^Y11 ; each is included R ^Y11 independently for halogen, cyano, Ci-C4-alkyl, G-Cg-cycloalkyl. C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; Q ^Y for O or S; Z for the fragments of the general formula (A1), (A2) or (A3);

where # is the connecting point to Y and where each stands T for O or S; R ^Z1 is phenyl unsubstituted or substituted by 1 to 4 R ^Z11 ; each is included R ^Z11 independently for halogen, cyano, nitro, SF5, C(Q ¹ )R ^a , C(O)OR ^a , C(Q ¹ )NR ^b R ^c , NR ^d R ^e , OR ^a , S(O) _n R ^a or SO ₂ NR ^b R ^c ; or for Ci-C ₆ -alkyl, Cz-Cg-alkenyl, C2-Cg-alkynyl or C-CS-cycloalkyl. all each unsubstituted or substituted by 1 to 5 R ^zla ; each is included R ^zla for halogen, cyano, Ci-C -alkyl. Ci-C -alkoxy. Ci -Cs-Thioalkyl. C'i-Cs-haloalkyl or Ci-Cs-haloalkoxy; R ^Z2 , R ^Z2a and R ^Z3 independently represent H; or for C(O)R ^a , C(O)OR ^a , C(O)NR ^b R ^c , S(O) _n R ^a ; or for Ci-Cg-alkyl, C ₂ -C ₆ -alkenyl, C ₂ -Cg-alkynyl or C ₃ -C6-cycloalkyl, each unsubstituted or substituted by 1 to 4 R ^Z21 ; or for phenyl or benzyl all in each case unsubstituted or substituted by 1 to 3 R ^Z21 ; each is included R ^Z21 independently for halogen, cyano, nitro, SF5, C(Q')R ^a . C(O)ORa ^{, C} (Q') ^NRb Rc . NR ^d R ^e , OR ^a , S(O) _n R ^a or SO ₂ NR ^b R ^c ; or for Ci-C ₄ -alkyl, Ci-C ₄ -haloalkyl, Ci-C ₄ -alkenyl, C ₂ -C ₄ -alkynyl or C -C 6 -cycloalkyl: or R ^Z2 and R ^Z3 together with the TCN moiety form a 5- to 7-membered ring; the R ^Z2 -R ^Z3 ring members consist of carbon atoms; up to 2 carbon atom ring members can independently consist of C(=O) and C(=S); wherein said R ^Z2 -R ^Z3 moiety is unsubstituted or substituted with from 1 to 4 R ^Z21 , where each is R ^Z21 independently for halogen, hydroxy, cyano, Ci-Cg-alkyl, Cs-Cg-cycloalkyl, Ci-Cg-haloalkyl, Ci-C ₄ -alkenyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy; or R ^Z2a and a second R ^Z2a together with the NCN moiety form a 5- to 7-membered ring; the R ^Z2a -R ^Z2a ring members consist of carbon atoms; up to 2 carbon atom ring members can independently consist of C(=O) and C(=S); this R ^Z2 -R ^Z3 unit is unsubstituted or substituted by 1 to 4 R ^Z21 ; each is included R ^a is independently Ci-Cg-alkyl, Cs-Cg-cycloalkyl, C ₂ -Cg-alkenyl or C ₂ -Cg- alkynyl, all of which may be unsubstituted in each case, or mono- to 5-fold with halogen and/or optionally may be substituted with an R ^f ; or phenyl unsubstituted or substituted by 1 to 3 R ^g ; R ^b and R ^c are independently H; or for Ci-Cg-alkyl, G-Cg-cycloalkyl. C ₂ -Cg-alkenyl or C ₂ -Cg-alkynyl, each of which can be unsubstituted or substituted once to 13 times with halogen and/or optionally with 1 to 2 R ^f ; or R ^b and R ^c together form a 3- to 7-membered ring; R ^d and R ^e are independently H, C (Q ¹ )R ^a . C(O) ^ORa ; or for Ci-Cg-alkyl, G-Cg-cycloalkyl, C ₂ -Cg-alkenyl or C ₂ -Cg-alkynyl, all of which may be unsubstituted in each case, or singly to 5 times with halogen and/or optionally with 1 to 2 R ^f substituted could be; or phenyl unsubstituted or substituted by 1 to 3 R ^g ; or R ^d and R ^e together form a 3- to 7-membered ring; R ^f independently for halogen, cyano, nitro, C ₃ -Cg-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfmyl, C1- C4-haloalkylsulphinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl; or phenyl or pyridyl, or a 5- or 6-membered heteroaromatic ring, each unsubstituted or substituted with 1 to 3 R ^g ; R ^g are independently halogen, cyano, nitro, Ci-C4-alkyl, _C3 -Cg-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci- C4-haloalkylthio, C1-C4-alkylsulphinyl, C1-C4-haloalkylsulfmyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl; R ^h is independently halogen, cyano, nitro, hydroxy, SF5, OSO2R ³ , SO2NR ^b R ^c , N(R ^d )(R ^e ), C(Q')NR ^b R ^c . NR^QQ^R ³ , C(O)R ^a , OC(O)R ^a or =Q ² ; or for C1-C4- _{AI kyl} , Ci-C4- _alkoxy , Ci-C4- _alkylthio , Ci-C4-alkylsulphinyl, Ci-C4-alkylsulfonyl, _C3 -Cg-cycloalkyl, spirocyclically bonded C2-Cg -Cycloalkyl, spirocyclically bound heterocyclyl with 3 to 7 ring atoms, C's-Cg-cycloalkylthio. C ₃ -Cg-cycloalkoxy, C ₃ -Cg-cycloalkylsulfmyl or C ₃ -Cg-cycloalkylsulfonyl, all of which can be unsubstituted or substituted once to 5 times by halogen and/or optionally by 1 to 2 R ^g ; or phenyl or a 4- to 7-membered saturated, partially saturated or aromatic heterocycle from the group consisting of furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl and isoxazolyl , thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2 ,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1, 2,4-triazinyl, 1,3,5-triazinyl, oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, or dihydroisoxazolyl, each unsubstituted or substituted with 1 to 2 R ^g Q ¹ independently represents O, S, N0R ^a or NCN; Q ² are independently O or N0R ^a ; and n is independently 0, 1 or 2. 3. A compound according to claim 1 or 2, wherein A is N or CR ^A ; stands by R ^A for H, halogen or Ci-C4-alkyl; V is -CQ^NR^RV ² ; stands by R ^V1 for C'i-Cfi-alkyl. C -Ck-cycloalkyl or a saturated C -Ch-Hctcrocyclyl from the series of

stands, where these substituents and P-01 to P-04 can all be unsubstituted in each case, or can ^optionally be substituted once to five times with halogen and/or with 1 to 2 Rh; RV2 for H; or for Ci-Cg-alkyl, Ci-Cg-alkoxy or C3-C?-cycloalkyl, all of which are unsubstituted or mono- to penta-substituted by halogen and/or optionally by 1 to 2 R ^g ; or R ^V1 and R ^V2 together with the nitrogen atom to which they are attached represent a heterocycle from the series U-01 to U-06

U-01 and U-02 U-03 U-04 U-05 U-06 where all U-01 to U-06 can each be unsubstituted or optionally substituted once to 5 times with halogen and/or optionally with 1 to 2 ^{rows R1} for H; stands for C 1 -C 4 -alkyl or C 2 -C 4 ^-alkenyl , all of which can be unsubstituted or substituted once to five times with halogen and/or optionally with 1 to 2 Rh; R ² represents the substructure of the general formula -XYZ; stands by X is phenyl or pyridyl, each unsubstituted or substituted by 1 to 3 R ^x ; stands by R ^x are independently halo, cyano; or for Ci-C4-alkyl, in each case unsubstituted or substituted by 1 to 2 R ^f ; Y for - CR ^Y1 =N- where N is bonded to Z, or for -NR ^Y2 -C(=Q ^Y )-, where C is bonded to Z; each is included R ^Y1 and R ^Y2 for H; or for Ci-C2-alkyl in each case unsubstituted or substituted by 1 to 3 R ^Y11 ; each is included R ^Y11 independently represent halogen, cyano, Ci-C2-alkyl or Ci-C2-alkoxy; Q ^{Y is} O or S; Z for the fragments of the general formula (A1), (A2) or (A3);

where # is the connecting point to Y and where each stands T for O or S; R ^Z1 is phenyl substituted with 1 to 3 R ^Z11 ; each is included R ^Z11 independently represent halogen, cyano, OR ^a SR ^a , or for Ci-C4-alkyl, Cs-Cg-cycloalkyl, all unsubstituted or substituted by 1 to 3 R ^zla ; each is included R ^zla for halogen, Ci-Cs-alkoxy or Ci-Cs-thioalkyl; R ^Z2 , R ^Z2a and R ^Z3 are independently H; or for Ci-C4-alkyl, in each case unsubstituted or substituted by 1 to 3 R ^Z21 ; each is included R ^Z21 independently of one another are halogen or C iG-alkoxy: or R ^Z2 and R ^Z3 together with the TCN moiety form a 5- to 6-membered ring; the R ^Z2 -R ^Z3 ring members consist of carbon atoms; 1 carbon atom ring member can consist of C(=O); this R ^Z2 -R ^Z3 unit is unsubstituted or substituted by 1 to 3 R ^Z21 ; each is included R ^Z21 independently for halogen, C iC -alkyl. C iG-Alcnyl. or C iC -alkoxy: each is included R ^a is independently Ci-Cg-alkyl, Cs-Cg-cycloalkyl, C2-Cg-alkenyl or C2-Cg-alkynyl, all of which may be unsubstituted in each case, or mono- to 5-fold with halogen and/or optionally with a R ^f may be substituted; or phenyl unsubstituted or substituted by 1 to 3 R ^g ; R ^f independently of one another are halogen, cyano, nitro, Cß-Cg-cycloalkyl, Cj-C -alkoxy. Ci-C4-haloalkoxy, Cj-C -alkylthio. Cj-C haloalkylthio. Cj-C alkylsulphinyl. C1-C4-haloalkylsulfmyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl; or phenyl or a 5- or 6-membered heteroaromatic ring each unsubstituted or substituted with 1 to 3 R ^g ; R ^g independently of one another are halogen, cyano, nitro, Ci-C4-alkyl, C's-Cg-cycloalkyl. Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfmyl, Ci-C4-haloalkylsulfmyl, C1-C4-alkylsulfonyl, Ci- C4-haloalkylsulfonyl, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl; R ^h independently for halogen, cyano, nitro, hydroxy, SF5, C1-C4-alkyl, C1-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfmyl, Ci-C4-alkylsulfonyl, C's-Cg-cycloalkyl . spirocyclically bound C2-Cg-cycloalkyl, spirocyclically bound heterocyclyl with 3 to 7 ring atoms, C's-Cg-cycloalkylthio. G-Cg-cycloalkoxy. Cs-Cg-cycloalkylsilfinyl, Cs-Cg-cycloalkylsulfonyl, all of which can be unsubstituted or substituted once to 5 times by halogen and/or optionally by 1 to 2 ^Rg ; or phenyl or a 4- to 7-membered saturated, partially saturated or aromatic heterocycle from the group consisting of furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1.2.3 -Triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1, 2,3-0-xadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1, 2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1, 3,5-triazinyl, oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, or dihydroisoxazolyl, all each unsubstituted or substituted with 1 to 2 R ^g ; Q ¹ for O; and n is 0, 1, or 2 A compound according to any one of claims 1 to 3, wherein A is N or CR ^A ; stands by R ^A for H; - II - WO 2022/053453 PCT/EP2021/074562 V is -C(O)NR ^V1 R ^V2 ; stands by R ^V1 for C'i-Cfi-alkyl. C -Ck-cycloalkyl or a saturated C -Ch-Hctcrocyclyl from the series of

P-01 P-04, where these substituents and P-01 and P-04 may all each be unsubstituted, or ^optionally substituted once to five times with halogen and/or with 1 to 2 Rh; R ^V2 for H; or for Ci-Cg-alkyl, Ci-Cg-alkoxy or C3-C?-cycloalkyl, all of which are unsubstituted or mono- to penta-substituted by halogen and/or optionally by 1 to 2 R ^g ; or R ^V1 and R ^V2 together with the nitrogen atom to which they are attached represent a heterocycle U-01;

U-01 where U-01 can in each case be unsubstituted or optionally substituted once to 3 times by halogen and/or optionally by 1 to 2 ^Rh ; R ^{1 is} Ci-C4-alkyl, each of which may be unsubstituted or mono- to tri-substituted by halogen and/or optionally by 1 to 2 Rh; R ² represents the substructure of the general formula -XYZ; stands by X is phenyl unsubstituted or substituted with 1 to 3 R ^x ; stands by R ^x independently represents halogen, cyano or methyl; Y for - CR ^Y1 =N- where N is bonded to Z, or for -NR ^Y2 -C(=Q ^Y )-, where C is bonded to Z; each is included R ^Y1 and R ^Y2 for H; Q ^Y for O; Z for the fragments of general formula (A1), (A2), (A3);

where # is the connecting point to Y and where each stands T for S; R ^Z1 is phenyl substituted with 1 to 3 R ^Z11 ; where 1 R ^Z11 is in 2-position and where each is standing R ^{Z11 is} independently F, Cl, Br, CH3, CH2CH3, CH2CH2CH3, CH(013)2, cyclopropyl, OCH3, OCH2CH3, OCH2CH2CH3, OCH(CH3) ₂ , _CH2OCH3 or CH(CH3 _{) OCH3} ; R ^Z2 , R ^Z2a and R ^Z3 independently represent H; or R ^Z2 and R ^Z3 together with the TCN moiety form a 5- to 6-membered ring; the R ^Z2 -R ^Z3 ring members consist of carbon atoms; 1 carbon atom ring member can consist of C(=O); this R ^Z2 -R ^Z3 unit is unsubstituted or substituted by 1 to 2 R ^Z21 ; each is included R ^{Z21 is} independently methyl; each is included R ^g independently of one another is halogen, cyano, Ci-Ci-alkyl, Cs-Cg-cycloalkyl, C1-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy; R ^h independently for halogen, cyano, nitro, hydroxy, Ci-C4-alkyl, C1-C4-AI koxy, Ci-C4-alkylthio, Ci-C4-alkylsulphinyl, C1-C4-alkylsulfonyl, C-Cg-cycloalkyl . spirocyclically bound C2-Cg-cycloalkyl, spirocyclically bound heterocyclyl with 3 to 7 ring atoms, C's-Cg-cycloalkylthio. G-Cg-cycloalkoxy. G-Cg-cycloalkylsulphinyl or Cs-Cg-cycloalkylsulfonyl, all of which may be unsubstituted or substituted once to 5 times with halogen and/or optionally with 1 to 2 R ^g ; or phenyl or a 4- to 7-membered saturated, partially saturated or aromatic heterocycle from the group consisting of furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1.2.3 -Triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1, 2,3-0-xadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1, 2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2, 4-triazinyl, 1,3, 5-triazinyl, oxetanyl, oxolanyl, dioxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, or dihydroisoxazolyl, each unsubstituted or substituted with 1 to 2 R ^g . A compound according to any one of claims 1 to 4, wherein A is N; V is -C(O)NR ^V1 R ^V2 ; stands by R ^V1 for trifluoromethylcyclohexyl, 3,3,3-trifluoropropyl, isopropyl, cyclohexyl, 4,4,4-trifluorobutyl, 4,4-difluorocyclohexyl, para-trifluoromethoxybenzyl, para-trifluoromethylbenzyl, trifluoromethoxyethyl, tetrahydrothiopyran, ( 1-cyanocyclopropyl)methyl or 1,1,2,2-tetrafluorobutyl, R ^{V2 is} H or methyl; or R ^V1 and R ^V2 together with the nitrogen atom to which they are attached for

R ¹ is methyl; R ² represents the substructure of the general formula -XYZ; stands by X is phenyl unsubstituted or substituted by 1 R ^x ; stands by R ^x is chloro, fluoro, cyano or methyl; Y is -CH=N-, where N is bonded to Z; each is included Z for the fragments of general formula (A2-1) or (A3-1); where # is the connecting point to Y and where each stands R ^Z1 is phenyl substituted with 1 to 2 R ^Z11 ; where 1 R ^Z11 is in 2-position and where each is standing R ^Z11 independently represent methyl, methoxy or isopropyl. 6. Formulation, in particular agrochemical formulation, comprising at least one compound of the formula (I) according to any one of claims 1 to 5. 7. Formulation according to claim 6 further comprising at least one extender and/or at least one surfactant 8. Formulation according to claim 6 or 7, characterized in that the compound of the formula (I) is present in a mixture with at least one other active ingredient. 9. A method for controlling pests, in particular animal pests, characterized in that a compound of the formula (I) as claimed in any of claims 1 to 6 or a formulation as claimed in any of claims 6 to 8 acts on the pests and/or their habitat leaves. 10. The method according to claim 9, characterized in that the pest is an animal pest and comprises an insect or an arachnid, or that the pest is an insect or an arachnid. 11. Use of a compound of formula (I) according to any one of claims 1 to 5 or a formulation according to any one of claims 6 to 8 for controlling animal pests. 12. Use according to claim 11, characterized in that the animal pest comprises an insect or an arachnid, or that the animal pest is an insect or an arachnid. 13. Use according to claim 11 or 12 in crop protection. 14. A method for protecting a seed or a germinating plant from pests, in particular animal pests, comprising a process step in which the seed is in contact with a compound of formula (I) according to any one of claims 1 to 5 or with a formulation according to any one of Claims 6 to 8 is brought. 15. Seed coated with a compound of formula (I) according to any one of claims 1 to 5 or with a formulation according to any one of claims 6 to 8.