WO2017016883A1

WO2017016883A1 - Process for preparation of cyclopentene compounds

Info

Publication number: WO2017016883A1
Application number: PCT/EP2016/066734
Authority: WO
Inventors: Karsten Koerber; Gopal Krishna DATTA; Pascal Bindschaedler; Wolfgang Von Deyn; Franz-Josef Braun
Original assignee: Basf Se
Priority date: 2015-07-24
Filing date: 2016-07-14
Publication date: 2017-02-02

Abstract

The present invention relates to a process for preparing cyclopentene compounds of formula (I) wherein the variables have the meaning as defined in the description, by cyclisation under basic conditions of a ketone of formula (II) which is obtained by reaction of a compound of formula (III) with a compound of formula (IV), novel compounds of formula (I), methods and use of these compounds and combinations for combating invertebrate pests such as insects, arachnids or nematodes in and on plants, and for protecting such plants being infested with pests, and for protecting plant propagation material as like seeds.

Description

Process for preparation of cyclopentene compounds

Description

The present invention relates to a process for preparing cyclopentene compounds of formula I

wherein

A is a group A¹ , A² or A³; wherein

A¹ is:

wherein

# denotes the attachment point to the remainder of the molecule;

W is O, or S;

Y is H, N(R⁵)R⁶, or OR⁹

is:

wherein

# denotes the attachment point to the remainder of the molecule;

A³ is a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated

heteromonocyclic ring containing 1 , 2, 3, or 4 heteroatoms N, O, and/or S as ring members, or

is a 8-, 9- or 10-membered saturated, partially or fully unsaturated heterobicyclic ring containing 1 , 2, 3, or 4 heteroatoms N, O, and/or S as ring members,

which ring may be substituted by one or more same or different R¹¹;

B¹, B² and B³ are each independently selected from N and CR², with the proviso that at most two of B¹ , B², and B³ are N;

G¹, G², G³ and G⁴ are each independently selected from N and CR⁴, with the proviso that at most two of G¹ , G², G³, and G⁴ are N;

R¹ is Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl-, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C₃-

Ce-halocycloalkyl, or C(=0)OR¹⁵;

each R² is independently H, halogen, CN, N₃, N0₂, SCN, SF₅, CrC₆-alkyl, C₃-C₈-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by one or more same or different R⁸,

Si(R ²)₃, OR⁹, S(0)_nR⁹, NR^10aR^10b,

phenyl which may be partially or fully substituted by R¹¹, and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially or fully unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or substituted by one or more same or different R¹¹ , preferably the unsubstituted or substituted HET;

R^3a, R^3b, R^3c are each independently H, halogen, OH, C0₂R^3d, Ci-C₃-alkyl, Ci-C₃-haloalkyl, C2-C3-alkenyl, C2-C3-alkynyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy, Ci-C3-alkylthio, C1-C3- haloalkylthio, Ci-C3-alkylsulfonyl and Ci-C3-haloalkylsulfonyl;

or R^3a and R^3b together form a group =0, =C(R^3e)₂, =NOH, or =NOCH₃;

R^3d is H, Ci-Ce-alkyl, or Ci-C₃-alkyloxy-Ci-C₃-alkyl;

each R^3e is independently H, halogen, CH3, or CF3;

each R⁴ is independently selected from the meanings mentioned for R²,

or two R⁴ bonded to adjacent carbon atoms may form a five- or sixmembered saturated,

partially or fully unsaturated carbocyclic ring;

each R⁵ is independently H, CN, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl,

C2-Cio-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by one or more same or different R⁸, or S(0)_nR⁹, or C(=0)R⁸;

each R⁶ is independently selected from the meanings mentioned for R²;

or R⁵ and R⁶, together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially or fully unsaturated heterocyclic ring, which ring may contain 1 , 2, 3 or 4 heteroatoms O, S, N, C=0 and/or C=S as ring members, which heterocyclic ring is unsubstituted or partially or fully substituted by same or different halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R⁸, or phenyl which may be partially or fully substituted by R¹¹;

or R⁵ and R⁶ together form a group =C(R⁸)₂, =S(0)_m(R⁹)₂, =NR^10a, or =NOR⁹;

R^7a, R^7b are each independently H, halogen, CN, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, or C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R⁸;

or R^7a and R⁴ in position G³ may together form a -ChbCI-b-chain;

each R⁸ is independently CN, N₃, NO2, SCN, SF₅, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, wherein the carbon chains may be substituted by one or more radicals R¹³;

Si(R¹²)₃, OR⁹, OSO2R⁹, S(0)_nR⁹, N(R^10a)R^10b, C(=O)N(R^10a)R¹⁰ , C(=S)N(R^10a)R¹⁰ , C(=0)OR⁹, CH=NOR⁹,

phenyl, which is unsubstituted or partially or fully substituted by same or different R¹⁶, or a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted or partially or fully substituted by same or different R¹⁶, or

two R⁸ present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyl group

together form a group =0, =C(R¹³)₂; =S; =S(0)_m(R¹⁵)₂, =S(0)_mR¹⁵N(R ^a)R , =NR ^0a, =NOR⁹; or =NN(R^10a)R¹⁰ ; or

two radicals R⁸, together with the carbon atoms of the alkyl, alkenyl, alkynyl or cycloalkyl group which they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, which heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, and which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶; and

R⁸ as a substituent on a cycloalkyi ring may additionally be Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R¹³; and

R⁸ in the groups C(=0)R⁸ and =C(R⁸)₂ may additionally be H, halogen, Ci-C₆-alkyl, Ci-Ce- haloalkyI, C₂-C6-alkenyl, C₂-C6-haloalkenyl, C₂-C6-alkynyl, or C₂-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R¹³;

each R⁹ is independently H, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-C8- cycloalkyl-Ci-C4-alkyl-, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, or C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R¹³, or

Ci-C₆-alkyl-C(=0)OR¹⁵,

C C₆-alkyl-C(=S)N(R ^a)R ^b, Ci-C₆-alkyl-C(=NR )N(R ^a)R ^b,

Si(R ²)₃, S(0)_nR¹⁵, S(0)_nN(R ^a)R ^b, N(R ^0a)R ^0b, N=C(R ³)₂, C(=0)R¹³,

C(=0)N(R ^a)R ^b, C(=S)N(R ^a)R ^b, C(=0)OR¹⁵, or

phenyl, which is unsubstituted, or partially or fully substituted by R¹⁶; and

a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶; and

R⁹ in the groups S(0)_nR⁹ and OS0₂R⁹ may additionally be d-C₆-alkoxy, or C C₆- haloalkoxy;

R^10a, R¹⁰ are independently from one another H, Ci-C₆-alkyl, Ci-Ce-haloalkyI, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R¹³;

Ci-C₆-alkyl-C(=0)OR¹⁵,

CrC₆-alkyl-C(=S)N(R ^a)R ^b, Ci-C₆-alkyl-C(=NR )N(R ^a)R ^b, C C₆-alkoxy, Ci-C₆-halo- alkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio,

S(0)_nR¹⁵, S(0)_nN(R ^a)R ^b, C(=0)R¹³, C(=0)OR¹⁵, C(=0)N(R ^a)R ^b,

C(=S)R¹³, C(=S)SR¹⁵, C(=S)N(R ^a)R ^b, C(=NR )R¹³;

phenyl, which is unsubstituted, or partially or fully substituted by same or different R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶, preferably unsubstituted or substituted HET; or

R^10a and R^10b form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially or fully unsaturated heterocyclic ring, which ring may additionally contain one or two heteroatoms N, O, and/or S as ring members, which ring is is unsubstituted, or partially or fully substituted by same or different halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs- Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, phenyl which may be partially or fully substituted by R¹⁶, and a 3-, 4-, 5-, 6,- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶; or

Rⁱo^a _{and R} ⁱo^b together form a group =C(R¹³)₂, =S(0)_m(R¹⁵)₂, =S(0)_mR¹⁵N(R^14a)R^14b, =NR¹⁴, or =NOR¹⁵;

R¹¹ is halogen, CN, N₃, N0₂, SCN, SF₅, Ci-Cio-alkyl, C₃-C₈-cycloalkyl, C₂-Cio-alkenyl, C2-C10- alkynyl, which groups are unsubstituted, partially or fully halogenated, and/or may be substituted by same or different R⁸, or

OR⁹, NR^10aR^10b, S(0)_nR⁹, Si(R ²)₃;

phenyl, which is unsubstituted, or partially or fully substituted by same or different R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated aromatic

heterocyclic ring comprising 1 , 2, 3, or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶; or two R¹¹ present on the same ring carbon atom of an unsaturated or partially unsaturated

heterocyclic ring may together form a group =0, =C(R¹³)₂, =S, =S(0)_m(R¹⁵)₂,

=S(0)_mR¹⁵N(R ^a)R ^b, =NR¹⁴, =NOR¹⁵, or =NN(R ^a)R ^b;

or two R¹¹ bound on adjacent ring atoms form together with the ring atoms to which they are bound a saturated 3-, 4-, 5-, 6-, 7-, 8- or 9-membered ring, which ring may contain 1 or 2 heteroatoms O, S, N, and/or NR¹⁴, and/or 1 or 2 groups C=0, C=S, C=NR¹⁴ as ring members, and which ring is unsubstituted, or partially or fully substituted by same or different halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C₂-C6-alkenyl, C₂-C6- haloalkenyl, C₂-C6-alkynyl, C₂-C6-haloalkynyl, phenyl which may be partially or fully substituted by same or different R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring containing 1 , 2, or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶;

each R¹² is independently Ci-C4-alkyl and phenyl, which is unsubstituted, or partially or fully substituted by same or different Ci-C4-alkyl;

each R¹³ is independently CN, N0₂, OH, SH, SCN, SF₅, d-C₆-alkoxy, Ci-C₆-haloalkoxy, SO_n- d-Ce-alkyl, SO_n-Ci-C₆-haloalkyl, Si(R ²)₃, -C(=0)N(R ^a)R ^b,

Cs-Cs-cycloalkyl which is unsubstituted, partially or fully halogenated or substituted by 1 or 2 same or different Ci-C4-alkyl, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and/or oxo; phenyl, benzyl, phenoxy, where the phenyl moiety may be substituted by one or more same or different R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring containing 1 , 2, or 3 heteroatoms N, O, and/or S, as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶; or

two R¹³ present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyi group may together be =0, =CH(Ci-C₄-alkyl), =C(Ci-C₄-alkyl)Ci-C₄-alkyl, =N(Ci-C₆-alkyl) or =NO(Ci- Ce-alkyl); and

R¹³ as a substituent of a cycloalkyi ring may additionally be Ci-C6-alkyl, C₂-C6-alkenyl or C₂-C6- alkynyl, which groups are unsubstituted, partially or fully halogenated, or substituted by 1 or 2 CN, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, and oxo; and R¹³ in groups =C(R ³)₂, N=C(R ³)₂, C(=0)R¹³, C(=S)R¹³, and C(=N R ⁴)R¹³ may additionally be H , halogen, Ci-C6-alkyl, C2-C6-alkenyl, or C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated, or substituted by 1 or 2 CN , C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, and oxo;

each R¹⁴ is independently H , CN , Ci-C₆-alkoxy, Ci-C₆-haloalkoxy, SO_n-Ci-C₆-alkyl, SO_n-Ci- Ce-haloalkyl, Si(R ²)₃;

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated, or substituted by 1 or 2 CN , Ci-C4-alkoxy, Ci-C4-haloalkoxy, SO_n-Ci-C4- alkyl, C3-C6-cycloalkyl which is unsubstituted or substituted by 1 or 2 substituents halogen and CN ;

and oxo;

Cs-Cs-cycloalkyI which is unsubstituted, or partially or fully halogenated or substituted by 1 or 2 CN , Ci-C₄-alkyl, Ci-C₄-alkoxy, Ci-C₄-haloalkoxy, SO_n-Ci-C₆-alkyl, C₃-C₄-cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl-, which groups are unsubstituted, or substituted by 1 or 2 substituents selected from halogen and CN ;

phenyl, benzyl, pyridyl, phenoxy, which cyclic moieties are unsubstituted, or substituted by one or more same or different halogen, CN , NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, and Ci-C6-alkoxycarbonyl; and a 3-, 4-, 5- or 6-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N , O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶;

R^14a and R^14b independently of each other, have one of the meanings given for R¹⁴; or

R^14a and R^14b, together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, partially, or fully unsaturated heterocyclic ring, wherein the ring may additionally contain 1 or 2 heteroatoms N , O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy, or Ci-C4-haloalkoxy; or

R^14a and R¹⁴ or R^14b and R¹⁴, together with the nitrogen atoms to which they are bound in the group C(=N R¹⁴)N(R^14a)R^14b, form a 3-, 4-, 5-, 6- or 7-membered partially, or fully unsaturated heterocyclic ring, wherein the ring may additionally contain 1 or 2

heteroatoms N , O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy, or C1-C4- haloalkoxy;

each R¹⁵ is independently H , CN , Si(R¹²)₃

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated, or substituted by 1 or 2 radicals C3-C4-cycloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, SO_n-Ci-C6-alkyl, or oxo;

Cs-Cs-cycloalkyI which is unsubstituted, partially or fully halogenated or substituted by 1 or 2 radicals Ci-C4-alkyl, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, SO_n-Ci-C6-alkyl, or oxo; phenyl, benzyl, pyridyl, and phenoxy, which rings are unsubstituted, partially or fully halogenated, or substituted by 1 , 2 or 3 substituents Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, or (Ci-C6-alkoxy)carbonyl;

each R¹⁶ is independently halogen, NO2, CN, OH, SH, d-Ce-alkoxy, Ci-Ce-haloalkoxy, SO_n- Ci-C6-alkyl, SO_n-Ci-C6-haloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, C1-C4- alkoxycarbonyl, Ci-C4-haloalkoxycarbonyl, aminocarbonyl, Ci-C4-alkylaminocarbonyl, di- (Ci-C4-alkyl)-aminocarbonyl, Si(R¹²)3;

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated, or substituted by 1 or 2 radicals CN, C3-C4-cycloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, or oxo;

Cs-Cs-cycloalkyI which is unsubstituted, partially or fully halogenated or substituted by 1 or 2 radicals CN, Ci-C4-alkyl, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, or oxo;

phenyl, benzyl, pyridyl and phenoxy, which rings are unsubstituted, partially or fully halogenated, or substituted by 1 , 2 or 3 substituents Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, or (Ci-C6-alkoxy)carbonyl; or

two R¹⁶ present together on the same atom of an unsaturated or partially unsaturated ring may be =0, =S, =N(Ci-C₆-alkyl), =NO-Ci-C₆-alkyl, =CH(Ci-C₄-alkyl), or =C(Ci-C₄-alkyl)₂; or

two R¹⁶ on two adjacent carbon atoms form together with the carbon atoms they are bonded to a 4-, 5-, 6-, 7- or 8-membered saturated, partially or fully unsaturated ring, wherein the ring may contain 1 or 2 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, or Ci-C4-haloalkoxy;

each n is independently 0, 1 , or 2; and

each m is independently 0, or 1 ; by cyclisation under basic conditions of a ketone of formula II

wherein the variables have the meanings given for formula I , and

Z is SiQ¹3 wherein

Q¹ is independently selected from Ci-C4-alkyl or phenyl; or

P(=0)Q²2 wherein Q² is independently selected from Ci-C4-alkyl, Ci-C4-alkoxy, phenyl, halophenyl, phenoxy, or halophenoxy;

obtained by reaction of a compound of formula II I

wherein Z is as defined for formula I I , and

M is a metal selected from Li, Mg, Zn, or Cu or a combination of one or two or three or four of the aforementioned metals, and

X is halogen,

p is 1 or 2; q is 1 , 2 or 3;

with an α , β unsaturated compound of formula IV, optionally in the presence of a catalyst,

In addition, the invention relates to novel compounds of formula I, which correspond to formulae IA, IB, IC, ID, and IE, resp., as defined below, as well as methods for controlling invertebrate pests, in particular arthropod pests and nematodes, by using these compounds and to plant propagation material and to agricultural and a veterinary compositions comprising said compounds.

Compounds of formula I in general and their pesticidal activity are known from

PCT/EP2015/052142. In view of the methods for preparing the compounds of formula I known from the aforementioned art, there is a need for a more efficient process for preparing the compounds of formula I which is applicable to technical scale manufacture. The present invention provides a highly efficient route to manufacture these compounds.

Cyclopentene compounds of formula I are obtained by cyclisation of an intermediate of formula II. Compounds of formula II are novel.

In formula II the variables have the meanings given for formula I, and

Z is is SiQ¹3 wherein Q¹ is independently selected from Ci-C4-alkyl or phenyl; or

P(=0)Q²2 wherein Q² is independently selected from Ci-C4-alkyl, Ci-C4-alkoxy, phenyl, halophenyl, phenoxy, or halophenoxy,

preferably Q¹ is C1-C4 alkyl, and Q² is independently selected from C1-C4 alkyl, more preferably Q¹ is independently selected from methyl, ethyl or propyl and Q² is independently selected from methyl, ethyl or propyl.

This transformation is usually carried out at temperatures of from -78°C to +150°C, preferably from -78°C to +80°C, in an inert solvent, in the presence of a base or an acid, preferably a base [cf. Ager, D. J., Science of Synthesis, 47a, 85-104; 2010; or Ager, D. J., Science of Synthesis, 4 (2001 ), p.789].

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and petrol ether, aromatic hydrocarbons such as toluene, 0-, m-, and p-xylene, ethers such as diethyl ether, diisopropyl ether, tert.-butylmethyl ether, dimethoxy ethylene, 1 ,4-dioxane, anisole, 2-methyl-tetrahydrofuran (2-CH₃-THF) and tetrahydrofuran (THF), preferably ethers such as diethyl ether, THF or 2-CH3-THF. It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as LiOH, NaOH, KOH and Ca(OH)2, alkali metal and alkaline earth metal oxides, such as U2O, Na20, CaO, and MgO, alkali metal and alkaline earth metal hydrides, such as LiH, NaH, KH and CaH₂, alkali metal and alkaline earth metal carbonates, such as U2CO3, K2CO3 and CaCC>3, and also alkali metal bicarbonates, such as NaHCC>3, alkali metal alcoholates, such as NaOCH3, NaOC2Hs, Na-tert.-butylate, K-tert.-butylate, moreover organic bases, for example tertiary amines, such as N(CH3)3, N(C2H5)3, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-di- methylaminopyridine, and also bicyclic amines, such as 1 ,8-diazabicyclo[5.4.0]undec-7-en (DBU) or 1 ,4-diazabicyclo[2.2.2]octan (DABCO); moreover organometallic bases, for example alkali metal alkyls such as methyl lithium, butyllithium, lithium naphthalide or metal amides, for example alkali metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane or hexamethyldisilazane. Preferred are organometallic bases, alkali metal alcoholates and alkali metal hydrides. Particular preference is given to bases selected from K2CO3, Na₂C0₃, Cs₂C0₃, DBU, DABCO, sodium bis(trimethylsilyl)amide

(NaHMDS), lithium bis(trimethylsilyl)amide (LiHMDS), K-tert-butoxide, Na-tert-butoxide, Li- diisopropylamide, NaH, KH, NaOCH₃, NaOC2H₅, NaOH, and KOH. The bases are generally employed in catalytic amounts; however, they can also be used in equimolar amounts, in excess or, if appropriate, as solvent.

Suitable catalysts are in general CuX¹, wherein X¹ is independently halogen or CN, optionally in the presence of L_pX_q ², wherein L is selected from Li, Na, K, Mg, Ca, Sc, Zn, and X² is selected independently from each other from halogen, OS(=0)2CF3, Ci-C6-alkoxy, or a lewis acid, such as for example from SiCI(CH₃)₃, CI₃SiH, SiCU, BF3OC2H5, SiF₄,

[(C2H5)3Si(toluene)][B(C₆F₅)₄], AgNTf₂, Me₃SiOTf, (CH₃)₃SiNTf2, (C₂H₅)3SiNTf₂, or (CH₃)₃SiCI0₄, TiCI₄, and SnCI₄, [PCH₃(C₆F₅)₄][I], or [PhsPCHzCeFsHCI], preferably SiCI(CH₃)₃, C SiH, SiCU, BF3OC2H5, SiF₄, (C₂H₅)3SiNTf₂, (CH₃)₃SiCI0₄, TiCI₄, or SnCI₄, (cf: Sereda et al., Topics in current chemistry, Vol. 291 , p. 349-393 (2010); Schinzer et al., Selectivities in Lewis acid promoted reactions. Kluwer Academic 1989, Dordrecht).

The lewis acid is used in 0.0001 to 2 preferably 0.001 to 1 , particularly 0.01 to 0.95 mol-% of compound II.

Suitable acids and acidic catalysts are in general anorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulphuric acid und perchloric acid, Lewis acids, such as boron tri fluoride, aluminium tri chloride, iron III chloride, tin IV chloride, titanium IV chloride and zinc II chloride, moreover organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, toluene sulphonic acid, benzene sulphonic acid, camphor sulphonic acid, citric acid, and trifluoro acetic acid. The acids are generally employed in catalytic amounts; however, they can also be used in equimolar amounts, in excess or, if appropriate, as solvent.

Compounds of Formula II are obtained by reaction of a metalorganic compound of formula IV. In formula IV the variable Z is defined as for formula II, and

M is a metal selected from Li, Mg, Zn, or Cu or a combination of one or two or three or four of the aforementioned metals, preferably Mg, Zn or Cu, and X is a nucleophilic leaving group, such as halogen, preferably CI, Br or I;

with an α , β unsaturated compound of formula III, wherein the variables are a s defined for formula I

transformation is usually carried out at temperatures of from -78°C to +100°C, preferably from - 50°C to +50°C, in an inert solvent, optionally in the presence of a catalyst [cf. Knochel et al., J. Org. Chem., 1988, 53 (10), pp 2390- 2392].

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and petrol ether, ethers such as diethyl ether, diisopropyl ether, tert.-butylmethyl ether, dimethoxy ethylene, 1 ,4-dioxane, anisole, 2-methyl tetrahydrofuran and tetrahydrofuran, preferably ethers such as diethyl ether, THF or 2-CH3-THF, nitrils such as acetonitrile, and propionitrile. It is also possible to use mixtures of the solvents mentioned.

Suitable acids and acidic catalysts are in general anorganic acids such as HF, HCI, HBr, H2SO4 and HCIO4, Lewis acids, such as BF₃, AICI₃, FeCI₃, ZnCI₄, TiCI₄ and ZnC , SiCI(CH₃)₃, CI3S1H, SiCI₄, BF3OC2H5, SiF₄, (C2H₅)3SiNTf₂, (CH₃)₃SiCI04, TiCI₄, or SnCI₄, moreover organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, toluene sulphonic acid, benzene sulphonic acid, camphor sulphonic acid, citric acid, and trifluoro acetic acid.

The catalyst is in particular CuX¹ , wherein X¹ is independently halogen or CN, optionally in the presence of L_pX_q ², wherein L is selected from Li, Na, K, Mg, Ca, Sc, Zn, and X² is selected independently from each other from halogen, OS(=0)2CF3, Ci-C6-alkoxy, preferably CuCN x 2 LiCI; or the catalyst is a lewis acid selected independently from SiCI(CH3)3, C SiH, SiCI₄, BF3OC2H5, SiF₄, [(C2H5)3Si(toluene)][B(C₆F₅)4], AgNTf₂, Me₃SiOTf, (CH₃)₃SiNTf2, (C₂H₅)3SiNTf₂, or (CH₃)₃SiCI0₄, TiCI₄, and SnCI₄, [PCH₃(C₆F₅)₄][I], or [Ph₃PCH₂C6F₅][CI] (cf. Lewis acid organocatalysts, Topics in current chemistry, Sereda Oksana; Tabassum Sobia; Wilhelm Rene Vol. 291 , p. 349-93 (2010); Schinzer D Selectivities in Lewis acid promoted reactions, Kluwer Academic, 1989, Dordrecht); preferably the lewis acid is selected from SiCI(CH3)3, C SiH, SiCI₄, and BF₃*OC₂H₅.

The catalyst is preferably used in an amount of 0.01 mol-% to 50 mol-% of compound III.

The acids are generally employed in catalytic amounts; however, they can also be used in equimolar amounts, in excess or, if appropriate, as solvent.

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

The starting materials required for preparing the compounds III, and IV, resp., are

commercially available or known from the literature [cf. Kitamura et al., Bulletin of the Chemical Society of Japan (2006), 79(10), 1552-1560; WO 2013/092943] or can be prepared in accordance with the literature cited.

The compounds of formula III are preferably obtained by condensation of a ketone of formula V with an acetyl compound of formula VI

This transformation is usually carried out at temperatures of from 0°C to +150°C, preferably from 20°C to +120°C, in an inert solvent, in the presence of a base [cf. WO 2013092943]

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and petrol ether, aromatic hydrocarbons such as toluene, o-, m-, and p-xylene, halogenated hydrocarbons such as CH2CI2, CHCI3, dichloroethane (DCE), and chlorobenzene, ethers such as diethyl ether, diisopropylether, tert.-butylmethyl ether, 1 ,4-dioxane, anisole, and THF, nitrils such as acetonitrile, and propionitrile, alcohols such as methanol (MeOH), ethanol, n-propanol, isopropanol, n-butanol, and tert.-butanol, preferably aliphatic hydrocarbons or halogenated hydrocarbons such as DCE. It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as LiOH, NaOH , KOH and Ca(OH)2, alkali metal and alkaline earth metal oxides, such as U2O, Na20, CaO, and MgO, alkali metal and alkaline earth metal hydrides, such as LiH, NaH, KH and Cahb, alkali metal and alkaline earth metal carbonates, such as L12CO3, K2CO3 and CaCC>3, and also alkali metal bicarbonates, such as NaHCC>3, moreover organic bases, for example tertiary amines, such as N(CH3)3, N(C2H5)3,

triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to alkali metal and alkaline earth metal carbonates and organic bases, especially sodium or potassium carbonate and triethylamine. The bases are generally employed in catalytic amounts; however, they can also be used in equimolar amounts, in excess or, if appropriate, as solvent. It is also possible to use mixtures of the bases mentioned.

The reaction mixtures are worked up in a customary manner, for example by mixing with water, separating the phases and, if appropriate, chromatographic purification of the crude products. Some of the intermediates and end products are obtained in the form of colorless or slightly brownish viscous oils which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion.

A further embodiment of the invention relates to a process for preparation of compounds of formula I , which correspond to the following formula:

wherein

R¹ is Ci-C4-haloalkyl or COOR¹⁵, preferably halomethyl, particularly CF₃;

R2a R2b _are independently H, CI, or F, preferably R^2a is H, and R^2b is F; R³ is H;

R^4A is halogen, CN, or Ci-C₄-alkyl, preferably F, CI, or CH₃;

R^5a is H or Ci-C₂-alkyl, preferably H or CH₃;

R⁶ is H, halogen, CN, N₃, N0₂, SCN, SF₅, Ci-C₆-alkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆- alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R⁸,

OR⁹, S(0)_nR⁹, NR^10aR^10b; or

phenyl which may be partially or fully substituted by R¹¹ ; or

3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially or fully unsaturated

heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹¹ , preferably the unsubstituted or substituted heterocyclic ring;

each R⁸ is independently CN, N₃, N0₂, SCN, SF₅, C₃-C8-cycloalkyl, C₃-C8-halocycloalkyl, wherein the carbon chains are unsubstituted, or substituted by one or more same or different R¹³;

OR⁹, OS0₂R⁹, S(0)_nR⁹, N(R ^0a)R ^0b, C(=O)N(R ^0a)R ^0b,

C(=S)N(R^10a)R^10b, C(=0)OR⁹, or CH=NOR⁹; or

phenyl which is unsubstituted, or partially or fully substituted by same or different R¹⁶; or 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or substituted by one or more same or different R¹⁶, preferably the unsubstituted heterocyclic ring, or

two R⁸ present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyi group

together form a group =0, =C(R ³)₂; =S; =S(0)_m(R ⁵)₂, =S(0)_mR ⁵N(R ^4a)R ^4b, =NR ^0a, =NOR⁹; or =NN(R^10a)R¹⁰ ; or

two radicals R⁸, together with the carbon atoms of the alkyl, alkenyl, alkynyl or cycloalkyi group which they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, which heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, and which ring is unsubstituted, or substituted by one or more same or different R¹⁶; and

R⁸ as a substituent on a cycloalkyi ring may additionally be Ci-C6-alkyl, Ci-C6-haloalkyl, C₂-C6- alkenyl, C₂-C6-haloalkenyl, C₂-C6-alkynyl, and C₂-C6-haloalkynyl, which groups are unsubstituted, or substituted by one or more same or different R¹³; and

R⁸ in=C(R⁸)₂ may additionally be H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C₂-C6-alkenyl, C₂-C6- haloalkenyl, C₂-C6-alkynyl, or C₂-C6-haloalkynyl, which groups are unsubstituted, or substituted by one or more same or different R¹³; and

R¹⁵ is H or Ci-C₄-alkyl.

Such compounds correspond to formula IA.

Compounds of formula IA are obtainable by the process outlined in the outset using the accordingly designed precursors of formulae I I , IV, V, and VI , resp., being I IA, IVA, VA, and VIA, resp., wherein the variables have the meanings as outlined for formula IA, and Z and MX are as defined in the outset. Compounds of formula IA are novel. Alternatively these compounds can be prepared also by processes known from prior art, e.g. WO2015/1 14157.

Compounds of formula I alternatively can be prepared by dehydrating a compound of formula 1 as shown below. A' is A or a precursor of A. Typical precursors of A are a halogen atom, CN, carboxy, CC>2-R^z1 , such as tert-butoxycarbonyl (carboxy and C(0)OR^z1 are of course only "precursors" if in the desired compound I W is S and/or R^z1 is not the desired radical R⁹ and/or if Y is to be -NR⁵R⁶), an acetale group, a protected aldehyde group or -OS02-R^z1 , where R^z1 is Ci- C4-alkyl, Ci-C4-haloalkyl or phenyl which may be substituted by 1 , 2 or 3 groups Ci-C4-alkyl, Ci- C4-haloalkyl Ci-C4-alkoxy, or Ci-C4-haloalkoxy. Compounds V correspond to compounds I in case A' is A.

Dehydration either occurs spontaneously or with the help of dehydrating agents, such as molecular sieves, acid-washed molecular sieves, magnesium sulfate, sodium sulfate, silica gel, SOC , POCI3, Burgess reagent, trifluoroacetic anhydride, p-toluene sulfonic acid, anhydrous HCI, or sulfuric acid. The water formed may alternatively be removed, e.g. by azeotropic distillation, e.g. with benzene/toluene as entrainer, e.g. using a Dean Stark trap. If necessary (i.e. if A' is a precursor of A), A' is then converted into a group A.

Compounds 1 wherein R^3a, R^3b and R^3c are hydrogen (in the following compounds 1a) can be prepared as shown below by reacting the cyclopentanone compound 2 with the Grignard reagent 3. Instead of the MgBr compound 3 the corresponding MgCI or Mgl compound can be used.

The cyclopentanone 2 can be prepared by decarboxylation of the carboxylic acid 8, e.g. under heat, as shown below. This acid can in turn be prepared by hydrolysis of the ester 7, where R' is a Ci-C4-alkyl group. Hydrolysis can be carried out under acidic or, preferably, basic conditions. Suitable bases are for example inorganic bases such as alkali metal hydroxides, e.g. LiOH, NaOH or KOH, or carbonates, such as Na2CC>3 or K2CO3. Alternatively, hydrolysis and decarboxylation can be carried out in a single step reaction using sulfuric acid, and water.

The ester 7 can be prepared as shown below by a Claisen (Dieckmann) condensation of the diester 9. R and R' are Ci-C4-alkyl groups. The condensation reaction is carried out in the presence of a strong base, such as NaOCH₃, NaOC₂H₅, KO'butyl, NaNH₂, NaH, or LDA.

The diester 9 can in turn be prepared in an addition of 11 to the acrylate 10, as shown below. X is MgZ, ZnZ or Li, where Z is CI, Br, or I. The addition reaction is generally carried out under condition suitable for Grignard reactions, especially under anhydrous conditions.

The acrylate 10 can be prepared from the ketone 12 in a Wittig reaction with 13, as shown below (Ph = phenyl).

Compounds 1 ', in which A' is a precursor of A can be converted as shown below into the different groups A¹ to A³. The conversion reactions apply all the same for all compounds I.

Compounds I, wherein A is a group A¹, in which W is O can be prepared by reacting a compound 1 ' wherein A' is CI, Br, I, or triflate with carbon monoxide in the presence of a palladium catalyst and an alcohol ROH, wherein R is Ci-C4-alkyl or R⁹, to a compound of formula 18. Suitable palladium catalysts are for example those described in WO 201 1/161 130.

This ester is then hydrolyzed to the respective carboxylic acid, which is the reacted under standard amidation conditions with an amine NHR⁵R⁶. Hydrolyzation can be carried out under standard conditions, e.g. under acidic conditions using for example hydrochloric acid, sulfuric acid or trifluoroacetic acid, or under basic conditions using for example an alkali metal hydroxide, such as LiOH, NaOH, or KOH. Amidation is preferably carried out by activation of the carboxylic acids with oxalylchloride [(COCI)2] or thionylchloride (SOCI2) to the respective acid chlorides, followed by reaction with an amine NHR⁵R⁶. Alternatively, amidation is carried out in the presence of a coupling reagent. Suitable coupling reagent (activators) are well known and are for instance selected from carbodiimides, such as DCC (dicyclohexylcarbodiimide) and DIC (diisopropylcarbodiimide), benzotriazol derivatives, such as HATU (0-(7-azabenzotriazol-1 -yl)- Ν,Ν,Ν',Ν'-tetramethyluronium hexafluorophosphate), HBTU ((0-benzotriazol-1-yl)-N,N,N',N'- tetramethyluronium hexafluorophosphate) and HCTU (1 H-benzotriazolium-1 -[bis(dimethyl- amino)methylene]-5-chloro tetrafluoroborate) and phosphonium-derived activators, such as BOP ((benzotriazol-1 -yloxy)-tris(dimethylamino)phosphonium hexafluorophosphate), Py-BOP ((benzotriazol-l-yloxy)-tripyrrolidinphosphonium hexafluorophosphate) and Py-BrOP (bromo- tripyrrolidinphosphonium hexafluorophosphate). Generally, the activator is used in excess. The benzotriazol and phosphonium coupling reagents are generally used in a basic medium.

Compounds 1.1 wherein A is a group A¹, wherein W is S, can be prepared by reacting the corresponding oxo-compound (W is O) with Lawesson's reagent (CAS 19172-47-5), see for example Jesberger et al., Synthesis, 2003, 1929-1958 and references therein. Solvents such as HMPA or THF at an elevated temperature such as 60°C to 100°C can be used. Preferred reaction conditions are THF at 65°C.

Compounds I wherein A is a group A², wherein R^7a and R^7b are hydrogen, can be prepared by reducing a compound 18 or 19 for example with LAH (lithium aluminium hydride) or DIBAL-H (diisobutyl aluminium hydride) to a compound 20.

This is then reacted in an SN reaction with an amine NHR⁵R⁶. For this purpose, the OH group can first be converted into a better leaving group, e.g. into a sulfonate (for example mesylate, tosylate or a triflate group). If R⁶ is a group -C(0)R⁸, it is alternatively possible to react compound 20 with an amine NH₂R⁵ and react then the resulting benzylic amine with an acid R⁸- COOH or a derivative thereof, such as its acid chloride R⁸-COCI, in an amidation reaction.

Compounds 1.1 wherein A is a group A², wherein R^7a is optionally substituted alkyl or optionally substituted cycloalkyl and R^7b is hydrogen, can be prepared by subjecting a ketone 22 (see below scheme 10), where R^7a is optionally substituted Ci-C6-alkyl or optionally substituted C3- Ce-cycloalkyl, to a reductive amination to furnish compounds 21 . Typical conditions for the reductive amination are: Reacting ketone 16 with an amine H2NR⁵ to yield the corresponding imine which is reduced to amine 21 with a reducing agent reagent such as NaBH₃CN. The reaction from ketone 22 to amine 21 may also be carried out as a one pot procedure.

The ketone 22 is prepared from the carbonyl compound 19 which is reacted with a Grignard reagent R^7a-MgHal, where Hal is CI, Br or I, or an organolithium compound R^7a-Li to obtain an alcohol of formula 23, which is then oxidized to a carbonyl compound of formula 22, as shown below.

For obtaining compounds in which R^7a and R^7b are optionally substituted alkyl, optionally substituted cycloalkyi, optionally substituted alkenyl or optionally substituted alkynyl, carbonyl compounds such as 22, where R^7a is optionally substituted Ci-C6-alkyl, optionally substituted C3-C8-cycloalkyl, optionally substituted C2-C6-alkenyl or optionally substituted C2-C6-alkynyl, is reacted with a Grignard reagent R^7b-MgHal, where Hal is CI, Br or I, or an organolithium compound R^7b-Li, where R^7b is optionally substituted Ci-C6-alkyl, optionally substituted C3-C8- cycloalkyl, optionally substituted C2-C6-alkenyl or optionally substituted C2-C6-alkynyl, to obtain an alcohol of formula 24.

Alcohol 24 can then be converted into amine 25 via the corresponding azide, as described, for example, in Organic Letters, 2001 , 3(20), 3145-3148.

If desired, this can be converted into compounds 1.1 wherein R⁵ and R⁶ are different from hydrogen, for example by standard alkylation or acylation reactions.

Compounds 1.1 wherein A is a group A², wherein R^7a is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyi or CN and R^7b is hydrogen, can be prepared by converting an aldehyde 19 into an imine 26 by reaction with an amine derivative NH₂R⁶, wherein R⁶ is tert-butyl sulfinyl, or, for preparing a compound with R^7a = CN, tosylate.

This imine is then reacted with a compound H-R^7a in an addition reaction under conditions as described for example in J. Am. Chem. Soc. 2009, 3850-3851 and the references cited therein, or, for introducing CN as a group R^7a, Chemistry - A European Journal 2009, 15, 1 1642-1 1659.

Compounds 1.1 wherein A is a group A², wherein both R^7a and R^7b are optionally substituted alkyl, alkenyl, alkynyl, cycloalkyi or CN, can be prepared analogously by converting a ketone 22, wherein R^7a is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyi or CN, into an imine by reaction with an amine derivative NH2R⁶, wherein R⁶ is tert-butyl sulfinyl, for preparing an imine compound 27.

This imine is then reacted with a compound H-R^7b in an addition reaction under conditions as described for example in J. Org. Chem 2002, 67, 7819-7832 and the references cited therein, or, for introducing CN as a group R^7a, Chemistry - A European Journal 2009, 15, 1 1642-1 1659. If desired, R⁶ can then be removed to yield an amino group Nh .

Compounds 19 can be prepared by reaction of a compound 1.1 ', in which A' is CI, Br, I or - OS02-R^z1 , where R^z1 is as defined above, with carbon monoxide and a hydride source, such as triethylsilane, in the presence of a transition metal complex catalyst, preferably a palladium catalyst, to the aldehyde 19. This reaction converts the starting group A' into a carbonyl group - C(=0)H.

Compounds 1.1 wherein A is A³ can be prepared by standard ring coupling reactions. For example, compounds, wherein A³ is an N-bound heterocyclic ring can be prepared by reacting a compound 1.1 ' wherein A' is CI, Br or I with the respective ring A³-H (H being on the nitrogen ring atom to be coupled) under Ullmann coupling conditions, such as described, for example, in WO 2007/075459. Typically, copper(l) iodide or copper(l) oxide and a ligand such as 1 ,2-cyclohexyl- diamine is used, see for example Kanemasa et al., European Journal of Organic Chemistry, 2004, 695-709. If A' is F, the reaction is typically run in a polar aprotic solvent such as N,N-di- methylformamide, Ν,Ν-dimethylacetamide or N-methylpyrrolidone, and in the presence of an inorganic base such as sodium, potassium or cesium carbonate.

Compounds, wherein A³ is a C-bound heterocyclic ring can be prepared by reacting a compound 1.1 ' wherein A' is Br or I with the boronic acid of the respective ring A³-B(OH)2 or the boro- nate ester of the respective ring A³-B(OR)2 under Suzuki reaction conditions via Pd-catalyzed cross coupling, such as described, for example, in WO 2007/075459. A typical catalyst is tetra- kis(triphenylphosphine)palladium(0). Solvents such as tetrahydrofuran, acetonitrile, diethyl ether and dioxane are suitable. The boronic acids A³-B(OH)2 are either commercially available or can be prepared by known methods. Other methods for introduction of the heterocyclic groups A³ are the Heck, Stille, Kumada and Buchwald-Hartwig coupling procedures; see for example Tetrahedron, 2004, 60, 8991-9016.

As a rule, the compounds of formula I including their stereoisomers, salts, and N-oxides, and their precursors in the synthesis process, can be prepared by the methods described above. If individual compounds can not be prepared via the above-described routes, they can be prepared by derivatization of other compounds I or the respective precursor or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds of formula (I) can advantageously be prepared from other compounds of formula (I) by derivati- zation, e.g. by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like, or by customary modifications of the synthesis routes described.

The reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or on silica gel. Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by

recrystallization or trituration.

A further embodiment of the invention relates to a process for preparation of compounds of formula I, which correspond to the following formula:

wherein

R¹ is CrC₄-haloalkyl or COOR¹⁵, preferably halomethyl, particularly CF₃;

R³ is H;

R⁶ is H, halogen, CN, N₃, N0₂, SCN, SF₅, Ci-C₆-alkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆- alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by one or more same or different R⁸,

OR⁹, S(0)_nR⁹, or NR^10aR^10b; or

phenyl which is unsubstituted, or substituted by one or more same or different R¹¹ ; or 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially or fully unsaturated

heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or substituted by one or more same or different R¹¹ , preferably the unsubstituted or substituted heterocyclic ring;

each R⁸ is independently CN, N₃, NO2, SCN, SF₅, C₃-C8-cycloalkyl, C₃-C8-halocycloalkyl, wherein the carbon chains are unsubstituted, or substituted by one or more same or different R¹³;

OR⁹, OSO2R⁹, S(0)_nR⁹, N(R^10a)R^10b, C(=O)N(R^10a)R^10b,

C(=S)N(R ^0a)R ^0b, C(=0)OR⁹, or CH=NOR⁹; or

phenyl which is unsubstituted, or substituted by one or more same or different R¹⁶; or 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2, or 3 heteroatoms N, O, and S as ring members, which ring is

unsubstituted, or substituted by one or more same or different R¹⁶, preferably the unsubstituted or substituted heterocyclic ring, or

together form a group =0, =C(R ³)₂; =S; =S(0)_m(R ⁵)₂, =S(0)_mR ⁵N(R ^4a)R ^4b, =NR ^0a, =NOR⁹; or =NN(R ^0a)R ^0b; or

two radicals R⁸, together with the carbon atoms of the alkyl, alkenyl, alkynyl or cycloalkyi group which they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, which heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, and which ring is unsubstituted, or substituted by one or more same or different R¹⁶; and R⁸ as a substituent on a cycloalkyl ring may additionally be Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl, which groups are unsubstituted, or substituted by one or more same or different R¹³; and

R⁸ in the groups C(=0)R⁸ and

may additionally be H, halogen, Ci-C6-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, or C2-C6-haloalkynyl, which groups are unsubstituted, or substituted by one or more same or different R¹³,

preferably R⁸ is independently CN, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, wherein the carbon chains are unsubstituted, or substituted by one or more same or different R¹³;

OR⁹, OSO2R⁹, S(0)_nR⁹, N(R ^0a)R ^0b, C(=O)N(R ^0a)R ^0b; or

a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2, or 3 heteroatoms N, O, and S as ring members, which ring is

unsubstituted, or substituted by one or more same or different R¹⁶, preferably the unsubstituted or substituted heterocyclic ring. Such compounds correspond to formula IB.

Compounds of formula IB are obtainable by the process outlined in the outset using the accordingly designed precursors of formulae II, IV, V, and VI, resp., being MB, IVB, VB, and VIB, resp., wherein the variables have the meanings as outlined for formula IB, and Z and MX are as defined in the outset.

Compounds of formula IB are novel. These compounds can be prepared also by processes known from prior art, e.g. WO2015/1 1415, as outlined above analogously for formula IA.

wherein

R¹ is Ci-C4-haloalkyl, preferably halomethyl, particularly CF3;

R^2a, R^2b are independently H, CI, or F, preferably R^2a is H, and R^2b is F;

R³ is H;

R^4A is halogen, CN, or Ci-C₄-alkyl, preferably CN;

A³ is is a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated

heteromonocyclic ring containing 1 , 2, 3, or 4 heteroatoms N, O, and/or S as ring members, which ring may be substituted by one or more same or different R¹¹ , preferably A³ is 1 -pyrazole, 2-oxazole, 2-thiazole or 1 ,2,4-triazole which rings are unsubstituted, or substituted by 0,1 or 2 R¹¹,

R¹¹ has one of the meanings given for R¹¹ above and is preferably halogen, CN, NO2, SCN, SF5, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, which groups are unsubstituted, partially or fully halogenated.

Such compounds correspond to formula IC. Compounds of formula IC are obtainable by the process outlined in the outset using the accordingly designed precursors of formulae II, IV, V, and VI, resp., being I IC, IVC, VC, and VIC, resp., wherein the variables have the meanings as outlined for formula IC, and Z and MX are as defined in the outset.

Compounds of formula IC are novel. These compounds can be prepared also by processes known from prior art, e.g. WO2015/1 1415, as outlined above.

wherein

R¹ is Ci-C4-haloalkyl, preferably halomethyl, particularly CF₃;

R^2a, R^2b are independently H, CI, or F, preferably R^2a is CI, and R^2b is F;

R³ is H;

R⁹ is H, CN, d-Ce-alkyl, Ci-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-Ci-C₄-alkyl-, C₃- Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, or C2-C6-haloalkynyl, which groups are unsubstituted, or substituted by one or more same or different SO_n-Ci-

Ce-alkyl, SO_n-Ci-C₆-haloalkyl, Si(R¹²)₃, C(=0)N(R ^a)R ; or

CrC₆-alkyl-C(=0)OR¹⁵, CrC₆-alkyl-C(=0)N(R ^a)R ^b,

CrC₆-alkyl-C(=S)N(R ^a)R ^b, Ci-C₆-alkyl-C(=NR )N(R ^a)R ^b,

Si(R ²)₃, S(0)_nR¹⁵, S(0)_nN(R ^a)R ^b, N(R ^0a)R ^0b, -N=C(R ³)₂, C(=0)R¹³,

C(=0)N(R ^a)R ^b, C(=S)N(R ^a)R ^b, C(=0)OR¹⁵; or

phenyl, which is unsubstituted, or substituted by one or more same or different R¹⁶; or 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or substituted by one or more same or different R¹⁶, preferably

R⁹ is H, d-Ce-alkyl, C C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-Ci-C₄-alkyl-, C₃-C₈- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, or C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different SO_n- Ci-C₆-alkyl, SO_n-Ci-C₆-haloalkyl, Si(R ²)₃, C(=0)N(R ^a)R ^b; N(R ^0a)R ^0b, C(=0)OR¹⁵; or 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶.

Such compounds correspond to formula ID.

Compounds of formula ID are obtainable by the process outlined in the outset using the accordingly designed precursors of formulae II, IV, V, and VI, resp., being IID, IVD, VD, and VID, resp., wherein the variables have the meanings as outlined for formula ID, and Z and MX are as defined in the outset.

Compounds of formula ID are novel. Alternatively, these compounds can be prepared also by processes known from prior art, e.g. WO2015/1 1415, as outlined above. A further embodiment of the invention relates to a process for preparation of compounds of formula I , which correspond to the following formula:

wherein

R¹ is Ci-C₄-haloalkyl or COOR¹⁵;

R^2a, R^2b are independently H , CI , or F, preferably R^2a is H , and R^2b is F;

R³ is H ;

R^4A is halogen, CN , or Ci-C₄-alkyl, preferably CI, or CH₃;

R⁶ is H , halogen, CN , N₃, N0₂, SCN , SF₅, Ci-C₆-alkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆- alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R⁸,

OR⁹, S(0)_nR⁹, N R^10aR^10b;

or R⁶ is phenyl which may be partially or fully substituted by R^{1 1} ; or

heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms N , O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R^{1 1} ;

R^7a is H , halogen, CN , Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, or C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R⁸;

each R⁸ is independently CN , N₃, NO2, SCN , SF₅, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, wherein the carbon chains are unsubstituted, or partially or fully substituted by same or different R¹³;

OR⁹, OSO2R⁹, S(0)_nR⁹, N(R ^0a)R ^0b, C(=O)N(R ^0a)R ^0b,

C(=S)N(R ^0a)R ^0b, C(=0)OR⁹, or CH=NOR⁹; or

phenyl unsubstituted, or partially or fully substituted by same or different R¹⁶; or

3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N , O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶, or

two R⁸ present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyi together form a group =0, =C(R ³)₂; =S; =S(0)_m(R ⁵)₂, =S(0)_mR ⁵N(R ^4a)R ^4b, =N R ^0a, =NOR⁹; or =N N (R ^0a)R ^0b; or

two R⁸, together with the carbon atoms of the alkyl, alkenyl, alkynyl or cycloalkyi which they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, which heterocyclic ring comprises 1 , 2, 3 or 4

heteroatoms N , O, and/or S as ring members, and which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶; and R⁸ as a substituent on a cycloalkyl ring may additionally be Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R¹³; and

R⁸ in the groups -C(=0)R⁸ and

may additionally be H, halogen, Ci-C6-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, or C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R¹³;

R⁹ is H, CN, d-Ce-alkyl, C C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-Ci-C₄-alkyl-, C₃- Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, or C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different SO_n- Ci-Ce-alkyl, SO_n-Ci-C₆-haloalkyl, Si(R¹²)₃, C(=0)N(R ^a)R ; or

Ci-C₆-alkyl-C(=0)OR¹⁵,

Si(R¹²)₃, S(0)_nR¹⁵, S(0)_nN(R ^a)R , N(R ^0a)R ⁰ , N=C(R¹³)₂, C(=0)R¹³,

C(=0)N(R ^a)R ^b, C(=S)N(R ^a)R ^b, C(=0)OR¹⁵; or

phenyl, which is unsubstituted, or partially or fully substituted by same or different R¹⁶; or

3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶; and

R¹⁵ is H or Ci-C₄-alkyl.

Such compounds correspond to formula IE.

Compounds of formula IE are obtainable by the process outlined in the outset using the accordingly designed precursors of formulae II, IV, V, and VI, resp., being HE, IVE, VE, and VIE, resp., wherein the variables have the meanings as outlined for formula IE, and Z and MX are as defined in the outset.

Compounds of formula IE are novel. Alternatively, these compounds can be prepared also by processes known from prior art, e.g. WO2015/1 1415, as outlined above. The organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix C_n- Cm indicates in each case the possible number of carbon atoms in the group.

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

The term "alkyl" as used herein and in the alkyl moieties of alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl and the like refers to saturated straight-chain or branched hydrocarbon radicals having 1 to 2 ("Ci-C₂-alkyl"), 1 to 3 ("C C₃-alkyl"),1 to 4 ("C C₄- alkyl"), or 1 to 6 ("Ci-C₆-alkyl"). Ci-C₄-Alkyl is methyl, ethyl, propyl, isopropyl, butyl, 1 - methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or 1 ,1 -dimethylethyl (tert-butyl).

The term "haloalkyl" as used herein, which is also expressed as "alkyl which is partially or fully halogenated", refers to straight-chain or branched alkyl groups having 1 to 4 ("Ci-C₄-haloalkyl"), carbon atoms (as mentioned above), wherein some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: in particular Ci-C2-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1- bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2- fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl.

"Halomethyl" is methyl in which 1 , 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like.

The term "alkenyl" as used herein refers to monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 ("C2-C3-alkenyl"), 2 to 4 ("C2-C4-alkenyl"), carbon atoms and a double bond in any position, for example C2-C3-alkenyl, such as ethenyl, 1 -propenyl, 2- propenyl or 1 -methylethenyl; C2-C4-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1 - methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 -propenyl, 2-methyl-1-propenyl, 1- methyl-2-propenyl or 2-methyl-2-propenyl.

The term "alkynyl" as used herein refers to straight-chain or branched hydrocarbon groups having 2 to 3 ("C2-C3-alkynyl"), 2 to 4 ("C2-C4-alkynyl") carbon atoms and one or two triple bonds in any position, for example C2-C4-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2- butynyl, 3-butynyl, 1 -methyl-2-propynyl and the like. The term "cycloalkyl" as used herein refers to mono- or bi- or polycyclic saturated hydrocarbon radicals having 3 to 8 ("Cs-Cs-cycloalkyl"), in particular 3 to 6 ("C3-C6-cycloalkyl") or 3 to 5 ("Cs-Cs-cycloalkyl") carbon atoms. Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl (C-C3H5), cyclobutyl (c- C4H7), cyclopentyl (C-C5H9) and cydohexyl (c-CeHu). Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.2.1]heptyl, bicyclo[3.1 .1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl. Preferably, the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical.

The term "cycloalkyl-Ci-C4-alkyl" refers to a Cs-Cs-cycloalkyl group ("C3-Cs-cycloalkyl-Ci-C4- alkyl"), preferably a C3-C6-cycloalkyl group ("C3-C6-cycloalkyl-Ci-C4-alkyl"), more preferably a C₃-C₄-cycloalkyl group ("C₃-C₄-cycloalkyl-CrC₄-alkyl") as defined above (preferably a monocyclic cycloalkyl group) which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above. Examples for C3-C6-cycloalkyl-Ci-C4-alkyl, apart those mentioned for C3-C4-cycloalkyl-Ci-C4-alkyl, are cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl. C3-C6-cycloalkylmethyl is for example cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl and cyclohexylmethyl.

The term "Ci-C2-alkoxy" is a Ci-C2-alkyl group, as defined above, attached via an oxygen atom. The term "Ci-C4-alkoxy" is a Ci-C4-alkyl group, as defined above, attached via an oxygen atom. The term "CrC6-alkoxy" is a Ci-C6-alkyl group, as defined above, attached via an oxygen atom. The term "CrCio-alkoxy" is a Ci-Cio-alkyl group, as defined above, attached via an oxygen atom. Ci-C4-Alkoxy is, for example, methoxy, ethoxy, n-propoxy, 1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1 - dimethylethoxy (tert-butoxy).

The term "Ci-C4-alkoxy-methyl" as used herein, refers to methyl in which one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above. The term "Ci-C6-alkoxy-methyl" as used herein, refers to methyl in which one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above. Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, pentyloxymethyl, hexyloxymethyl and the like.

The term "SO_n-Ci-C6-alkyl" is a Ci-C6-alkyl group, as defined above, attached via a sulfur atom, in case n is 0 (also referred to as alkylthio group). If n is 1 , the term refers to a Ci-C6-alkyl group attached via a sulfinyl group (also referred to as alkylsulfinyl group). If n is 2, the term refers to a Ci-C6-alkyl group attached via a sulfonyl group (also referred to as alkylsulfonyl group).

The substituent "oxo" replaces a Chb group by a C(=0) group.

The term "alkylcarbonyl" is a d-Ce-alkyl ("Ci-C₆-alkylcarbonyl"), preferably a Ci-C₄-alkyl ("Ci- C₄-alkylcarbonyl") group, as defined above, attached via a carbonyl [C(=0)] group. Examples are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl, isopropylcarbonyl, n- butylcarbonyl and the like. The term "haloalkylcarbonyl" is a Ci-C6-haloalkyl ("C1-C6- haloalkylcarbonyl"), preferably a Ci-C₄-haloalkyl ("Ci-C₄-haloalkylcarbonyl") group, as defined above, attached via a carbonyl [C(=0)] group. Examples are trifluoromethylcarbonyl, 2,2,2- trifluoroethylcarbonyl and the like.

The term "alkoxycarbonyl" is a Ci-C6-alkoxy ("Ci-C6-alkoxycarbonyl"), preferably a Ci-C₄- alkoxy ("Ci-C₄-alkoxycarbonyl") group, as defined above, attached via a carbonyl [C(=0)] group. Examples are methoxycarbonyl), ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n- butoxycarbonyl and the like. The term "Ci-C₄-alkylamino" is a group -N(H)Ci-C₄-alkyl. Examples are methylamino, ethylamino, propylamino, isopropylamino, butylamino and the like. The term "di-(Ci-C₄-alkyl)amino" is a group -N(Ci-C₄-alkyl)₂. Examples are dimethylamino, diethylamino, ethylmethylamino, dipropylamino, diisopropylamino, methylpropylamino, methylisopropylamino, ethylpropylamino, ethylisopropylamino, dibutylamino and the like.

The term "Ci-C₄-alkylaminocarbonyl" is a group -C(0)N(H)Ci-C₄-alkyl. Examples are methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, isopropylaminocarbonyl, butylaminocarbonyl and the like.

The term "3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially or fully unsaturated heterocyclic ring containing 1 , 2 or 3 (or 4) heteroatoms N, O, and/or S, as ring members" denotes a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or fully unsaturated heteromonocyclic ring or a 8-, 9- or 10-membered saturated, partially or fully unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms which are selected from N, O, and S as ring members. Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond(s). Fully unsaturated rings contain as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the ring size. Fully unsaturated include aromatic heterocyclic rings. The heterocyclic ring may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. Of course, the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent. N and S ring atoms may be oxidized, if not mentioned otherwise. The oxidized ring atoms constitue an N- oxide, Sulfoxide (SO), and a sulfone (SO2), resp., wherein the only the N- or S atom is a ring member.

Examples of a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heteromonocyclic ring include: Oxiranyl, thiiranyl, aziridinyl, oxetanyl, thietanyl, azetidinyl, tetrahydro- furan-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1-yl, pyrroli- din-2-yl, pyrrolidin-3-yl, pyrazolidin-1 -yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imida- zolidin-1-yl, imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl, oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxazolidin-3-yl, isoxazolidin-4-yl, isoxazolidin-5-yl, thiazolidin-

2- yl, thiazolidin-3-yl, thiazolidin-4-yl, thiazolidin-5-yl, isothiazolidin-2-yl, isothiazolidin-3-yl, iso- thiazolidin-4-yl, isothiazolidin-5-yl, 1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4-oxadiazolidin-5-yl, 1 ,2,4-thiadi- azolidin-3-yl, 1 ,2,4-thiadiazolidin-5-yl, 1 ,2,4-triazolidin-3-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4-thia- diazolidin-2-yl, 1 ,3,4-triazolidin-1-yl, 1 ,3,4-triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydro- pyranyl, 1 ,3-dioxan-5-yl, 1 ,4-dioxan-2-yl, piperidin-1 -yl, piperidin-2-yl, piperidin-3-yl, piperidin-4- yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-2-yl, hexahydro- pyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1 -yl, piperazin-2-yl, 1 ,3,5-hexahydrotriazin-1- yl, 1 ,3,5-hexahydrotriazin-2-yl and 1 ,2,4-hexahydrotriazin-3-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl, thiomorpholin-4-yl, 1-oxothiomorpholin-2- yl, 1 -oxothiomorpholin-3-yl, 1 -oxothiomorpholin-4-yl, 1 ,1-dioxothiomorpholin-2-yl, 1 ,1-dioxothio- morpholin-3-yl, 1 ,1-dioxothiomorpholin-4-yl, azepan-1-, -2-, -3- or -4-yl, oxepan-2-, -3-, -4- or -5- yl, hexahydro-1 ,3-diazepinyl, hexahydro-1 ,4-diazepinyl, hexahydro-1 ,3-oxazepinyl, hexahydro- 1 ,4-oxazepinyl, hexahydro-1 , 3-dioxepinyl, hexahydro-1 , 4-dioxepinyl and the like. Examples of an 8-membered saturated heterocyclic ring include: oxocanyl, azocanyl, 1 ,2-, 1 ,3-, 1 ,4- and 1 ,5- diazocanyl and the like.

Examples of a 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclic ring include: 2,3- dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl,

3- pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-

4- yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2- isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isoth iazoli n-4-y 1 , 3-isothiazolin-4-yl, 4- isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1- yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-

5- yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyra- zol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropy- razol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydro- oxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydro- oxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetra- hydropyrazinyl, 1 ,3,5-di- or tetrahydrotriazin-2-yl, 1 ,2,4-di- or tetrahydrotriazin-3-yl, 2,3,4,5-tetra- hydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1 H]aze- pin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydrooxepinyl, such as 2,3,4,5-tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahy- dro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydro-1 ,3-diazepinyl, tetrahydro-1 ,4-diazepinyl, tetrahydro-1 ,3-oxazepinyl, tetrahydro-1 , 4-oxazepinyl, tetrahydro-1 , 3-dioxepinyl and tetrahydro- 1 , 4-dioxepinyl. Examples of an 8-membered partially unsaturated heterocyclic ring include: dihydroazocinyl, tetrahydrazocinyl, hexahydroazocinyl and the like.

Examples for a 3-, 4-, 5-, 6- or 7-membered fully unsaturated (including aromatic) heterocyclic ring are 5- or 6-membered heteroaromatic rings, such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1- pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1 -pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4- oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1 -imidazolyl, 2-imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-1-yl, 1 ,3,4-triazol-2-yl, 1 ,2,4-triazol-1-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1 -oxo- pyridin-2-yl, 1 -oxopyridin-3-yl, 1 -oxopyridin-4-yl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl, and also homoaromatic radicals, such as 1 H-azepine, 1 H-[1 ,3]-diazepine and 1 H-[1 ,4]-diazepine. Examples of an 8-membered fully unsaturated saturated heterocyclic ring include: azocinyl, 1 ,2-, 1 ,3-, 1 ,4- and 1 ,5-diazocinyl and the like.

A group of preferred heterocycles is the following: 2-pyridyl (E-1 ), 3-pyridyl (E-2), 4-pyridyl (E- 3), 3-pyridazinyl (E-4), 4-pyrimidinyl (E-5), 2-pyrazinyl (E-6), 2-pyrimidinyl (E-7), thiophen-2-yl (E-8), thiophen-3-yl (E-9), furan-2-yl (E-10), and furan-3-yl (E-1 1 ); heterocycles E-1 , E-2, and E- 7 are particularly prefered, which rings E-1 to E-1 1 are unsubstituted or substituted by up to 3 same or different substituents.

Another particulary preferred heterocycle is 1 ,2,4-triazol-1 -yl.

Preferred 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic rings comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members (HET) are in any positions of formula I, the following: azetidin-3-yl (H-1 ), dioxin-6-yl (H-2), 1 ,3-dioxolan-2-yl (H-3), 1 ,1- dioxotetrahydrothiophen-3-yl (H-4), 1 ,1-dioxothietan-2-yl (H-5), 1 ,1 -dioxothietan-3-yl (H-6), imidazol-2-yl (H-7), imidazol-4-yl (H-8), imidazol-5-yl (H-9), isothiazol-3-yl (H-10), isothiazol-4-yl (H-1 1 ), isothiazol-5-yl (H-12), isoxazol-3-yl (H-13), isoxazol-4-yl (H-14), isoxazol-5-yl (H-15), is- oxazolidin-4-yl (H-16), oxazol-2-yl (H-17), oxazol-4-yl (H-18), oxazol-5-yl (H-19), oxethan-3-yl (H-20), 3-oxoisoxazolidin-4-yl (H-21 ), 2-oxopyrrolidin-3-yl (H-22), 2-oxotetrahydrofuran-3-yl (H- 23), [1 ,3,4]-thiadiazol-2-yl (H-24), [1 ,2,3]-thiadiazol-4-yl (H-25), [1 ,2,3]-thiadiazol-5-yl (H-26), thiazol-2-yl (H-27), thiazol-4-yl (H-28), thiazol-5-yl (H-29), thien-2-yl (H-30), thien-3-yl (H-31 ), thietan-2-yl (H-32), thietan-3-yl (H-33), 1 -oxothietan-2-yl (H-34), 1-oxothietan-3-yl (H-35), 1 -oxo- tetrahydrothiophen-3-yl (H-36), tetrahydrofuran-2-yl (H-37), tetrahydrofuran-3-yl (H-38), tetra- hydrothiophen-3-yl (H-39), pyrazin-2-yl (E-6), pyrazol-3-yl (H-40), 2-pyridyl (E-1 ), 3-pyridyl (E-2),

4- pyridyl (E-3), pyridazin-3-yl (E-4), pyridazin-4-yl (H-41 ), 2-pyrimidinyl (E-7), 4-pyrimidinyl (E-5),

5- pyrimidinyl (H-42), and pyrrolidin-3-yl (H-43). More preferred rings HET are the following: E-1 , E-7 and H-6, H-21 , H-33 and H-35. Rings E-2 and E-7 are particularly preferred.

With respect to the variables, the particularly preferred embodiments of the intermediates correspond to those of the groups of the formula I.

The remarks made below concerning preferred embodiments of the variables of the

compounds of formula I, the features of the use and method according to the invention and of the composition of the invention are valid both on their own and, in particular, in every possible combination with each other.

In one embodiment of formula I compounds, A is A¹.

In a preferred embodiment of A¹, W is O.

In one embodiment of A¹, Y is N(R⁵)R⁶; wherein R⁵ and R⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings:

R⁵ is H, d-Cs-alkyl, C₃-C₄-alkenyl, C₃-C₄-alkynyl, CH₂CN or Ci-C₂-alkoxy-CrC₂-alkyl; R⁶ is H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl which is unsubstituted or substituted by one R⁸; C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl which is

unsubstituted or substituted by 1 or 2 substituents F or CN;

N(R^10a)R^10b, CH=NOR⁹;

phenyl which is unsubstituted or substituted by one or more same or different substituents

R¹¹; wherein

R⁸ is selected from CN, Cs-Cs-cycloalkyl which optionally carries a CN, C3-C8- halocycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, C(=O)N(R^10a)R^10b, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substituents R¹⁶, and a heterocyclic ring selected from rings E-1 to E-11 as defined below; wherein

R^10a in C(=O)N(R^10a)R^10b as a meaning for R⁸ is H or Ci-C₆-alkyl;

R^10b in C(=O)N(R^10a)R¹⁰ as a meaning for R⁸ is H, C C₆-alkyl, C₂-C₄-alkynyl, CH₂- CN, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C₄-alkoxy or

Ci-C₄-haloalkoxy,

R⁹ is H, Ci-Ce-alkyl or Ci-Ce-haloalkyI;

R^10a in -N(R^10a)R^10b as a meaning for R⁶ is H;

R^10b in -N(R^10a)R^10b as a meaning for R⁶ is -C(=0)N(R^14a)R^14b or a heteroaromatic ring selected from rings of formulae E-1 to E-1 1 as defined above; wherein

R^14a is H or Ci-Ce-alkyl; and

R¹⁴ is H, Ci-Ce-alkyl, Ci-Ce-haloalkyI, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆- halocycloalkyl, CH2-CN, Ci-C₄-alkoxy or Ci-C₄-haloalkoxy; and R¹¹ and R¹⁶; independently of each occurrence and independently of each other, are

halogen, CN, nitro, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy, Ci-C₄-haloalkoxy, Ci-

C₄-alkylthio, Ci-C₄-haloalkylthio, Ci-C₄-alkylsulfinyl, Ci-C₄-haloalkylsulfinyl, C1-C4- alkylsulfonyl, Ci-C₄-haloalkylsulfonyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C₄-haloalkenyl, C2-C₄-alkynyl, C2-C₄-haloalkynyl, CrC₄-alkylcarbonyl, Ci- C₄-haloalkylcarbonyl, aminocarbonyl, Ci-C₄-alkylaminocarbonyl and di-(CrC₄-alkyl)- aminocarbonyl; or

two R¹¹ present on the same carbon atom of a saturated heterocyclic ring may form together =0 or =S; or

two R¹⁶ present on the same carbon atom of a saturated heterocyclic ring may form together =0 or =S.

More preferred, in N(R⁵)R⁶ as a radical Y,

R⁵ is H;

R⁶ is N(R ^0a)R ^0b; CH=NOR⁹; wherein

R⁹ is selected from Ci-C6-alkyl and Ci-C6-haloalkyl;

R^10a is H;

R^10b is a heteroaromatic ring of formulae E-1 to E-11 , or H-6, H-21 , H-33 and H-35 as defined above, wherein

R^14a is H or Ci-Ce-alkyl; and R^14b is H, Ci-Ce-alkyI, Ci-Ce-haloalkyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆- halocycloalkyl, CH2-CN, Ci-C₄-alkoxy or Ci-C₄-haloalkoxy; and R¹¹ and R¹⁶; independently of each occurrence and independently of each other, are

selected from halogen, CN, NO2, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy, Ci-C₄- haloalkoxy, Ci-C₄-alkylthio, Ci-C₄-haloalkylthio, Ci-C₄-alkylsulfinyl, Ci-C₄- haloalkylsulfinyl, CrC₄-alkylsulfonyl, CrC₄-haloalkylsulfonyl, C3-C6-cycloalkyl, C3- C6-halocycloalky, Ci-C₄-alkylcarbonyl, CrC₄-haloalkylcarbonyl, aminocarbonyl, Ci- C₄-alkylaminocarbonyl and di-(Ci-C₄-alkyl)-aminocarbonyl. In another embodiment, in A¹ Y is H.

In further another embodiment, in A¹ Y is OR⁹. R⁹ has one of the above general meanings, or, in particular, is selected from H, Ci-C6-alkyl, Ci-C6-haloalkyl and Ci-C6-alkyl substituted by one radical R¹³, where R¹³ has one of the above general meanings, or, in particular, one of the following preferred meanings: CN, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl and a heterocyclic ring selected from E-1 to E-1 1 as defined above, which rings are unsubstituted or substituted by up to 3 R¹⁶;wherein

each R¹⁶ is independently selected from halogen, CN, NO2, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci- C₄-alkoxy, Ci-C₄-haloalkoxy, Ci-C₄-alkylthio, Ci-C₄-haloalkylthio, Ci-C₄-alkylsulfinyl, Ci-

C₄-haloalkylsulfinyl, Ci-C₄-alkylsulfonyl, Ci-C₄-haloalkylsulfonyl, C₃-C6-cycloalkyl, C₃-C6- halocycloalkyl, C2-C₄-alkenyl, C2-C₄-haloalkenyl, C2-C₄-alkynyl, C2-C₄-haloalkynyl, Ci-C₄- alkylcarbonyl, Ci-C₄-haloalkylcarbonyl, aminocarbonyl, Ci-C₄-alkylaminocarbonyl and di- (Ci-C₄-alkyl)aminocarbonyl; or

two R¹⁶ present on the same carbon atom of a saturated ring may form together =0 or =S.

In particular R⁹ is selected from H, Ci-C6-alkyl and Ci-C6-haloalkyl, and specifically from H and Ci-Ce-alkyI.

More preferably, in A¹, W is O and Y is -N(R⁵)R⁶.

In alternatively more preferred embodiment, in A¹, W is O and Y is H.

In another embodiment, in A¹, W is O and Y is OR⁹, wherein R⁹ has one of the above general meanings, or, is preferably H, Ci-C6-alkyl, Ci-C6-haloalkyl and Ci-C6-alkyl substituted by one radical R¹³, where R¹³ has one of the above general meanings, or, is preferably CN, Ci-C6-alk- oxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkyl- sulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl and a heterocyclic ring selected from rings E-1 to E-1 1 as defined above. Preferably W is O and R⁹ is H, Ci-C6-alkyl or Ci-C6-haloalkyl, and perferably H or Ci-C6-alkyl.

Compounds I wherein Y is OR⁹ have biological activity, but are also useful as intermediate compounds in the preparation of compounds I wherein Y is N(R⁵)R⁶. Thus, the invention also relates to intermediate compounds I wherein A is A¹ wherein Y is -OR⁹, wherein R⁹ has one of the above-defined general meanings or, preferably, one of the above-defined preferred meanings; and to the use of such compounds in the preparation of compounds I wherein Y is N(R⁵)R⁶. Compounds I wherein Y is H have biological activity, too, but are especially useful as intermediate compounds in the preparation of compounds I wherein Y is N(R⁵)R⁶. Thus, the invention also relates to intermediate compounds I wherein A is A¹ wherein Y is H; and to the use of such compounds in the preparation of compounds I wherein Y is N(R⁵)R⁶.

In N(R⁵)R⁶ as a radical Y, preferably

R⁵ is selected from H, Ci-C6-alkyl, C2-C3-alkynyl and Ch -CN, particularly H or Ci-C3-alkyl; and

R⁶ is selected from H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl which carries one radical R⁸, wherein R⁸ is as defined below; C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6- cycloalkyl which may be substituted by 1 or 2 substituents selected from F, CN and pyridyl;

N(R^10a)R^10b, wherein R^10a is selected from hydrogen and CrC₆-alkyl and R^10b is selected from hydrogen, C(=0)N(R^14a)R^14b, wherein R^14a is selected from H and Ci-C₆-alkyl and

R^14b is selected from the group consisting of H, Ci-C6-alkyl, C2-C4-alkynyl, CH2-CN, C1-C6- haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; phenyl which is unsubstituted or substituted by one or more same or different, in particular 1 , substituents R¹⁶, wherein each R¹⁶ independently has one of the meanings given below for R¹¹ ; and a heteroaromatic ring selected from rings E-1 , E-2 and E-7 as defined above, where however each R¹⁶ has independently one of the meanings given below for R¹¹; CH=NOR⁹, wherein R⁹ is selected from H, C C₆-alkyl and d-C₆-haloalkyl;

phenyl which is unsubstituted or substituted by one or more same or different, preferably 1 , 2 or 3, in particular 1 , substituents R¹¹ , wherein R¹¹ is as defined below;

each R¹¹ is independently selected from the group consisting of halogen, CN, NO2, Ci-

C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, C1-C4- haloalkylsulfonyl, C₃-C6-cycloalkyl, C₃-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkylcarbonyl, C1-C4- haloalkylcarbonyl, aminocarbonyl, Ci-C4-alkylaminocarbonyl and di-(Ci-C4-alkyl)- aminocarbonyl; or

two R¹¹ present on the same carbon atom of a saturated heterocyclic ring may form together =0 or =S;

R⁸ is selected from OH, CN, Cs-Cs-cycloalkyl which optionally carries a CN substituent, C3-C8-halocycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, CrC₆-haloalkylsulfinyl, CrC₆-alkylsulfonyl, C1-C6- haloalkylsulfonyl, -C(=O)N(R^10a)R^10b, phenyl which is unsubstituted or partially or fully substituted by, preferably 1 , 2 or 3, in particular 1 , same or different R¹⁶, and a heterocyclic ring selected from rings E-1 to E-1 1 as defined above;

wherein

R^10a is H or Ci-C₆-alkyl;

R^10b is H, d-Ce-alkyl, Ci-C₆-haloalkyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆- halocycloalkyl, CH₂-CN, Ci-C6-alkoxy or Ci-C6-haloalkoxy; and each R¹⁶ as a substituent on phenyl or heterocyclic rings E-1 to E-1 1 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci- C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4- alkynyl, C2-C4-haloalkynyl, CrC4-alkylcarbonyl, CrC4-haloalkylcarbonyl, aminocarbonyl, Ci-C4-alkylaminocarbonyl and di-(Ci-C4-alkyl)-aminocarbonyl; or two R¹⁶ present on the same carbon atom of a saturated heterocyclic ring may form together =0 or =S.

Even more particularly, in N(R⁵)R⁶ as a radical Y,

R⁵ is H;

R⁶ is selected from H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl substituted by one R⁸, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl which may be substituted by 1 or 2 substituents selected from F and CN;

N(_Rioa)_Riob_; CH=NOR⁹;

phenyl which is unsubstituted or partially or fully substituted by R¹¹ ;

wherein

R⁸ is CN, Cs-Ce-cycloalkyI which is unsubstituted or substituted by a CN;

C3-C8-halocycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, CrC₆-haloalkylsulfinyl, CrC₆-alkylsulfonyl, C1-C6- haloalkylsulfonyl, -C(=O)N(R^10a)R^10b, phenyl which is unsubstituted or substituted by one or more same or different R¹⁶, and a heterocyclic ring selected from rings E-1 to E-1 1 as defined above; wherein

R^10a in C(=O)N(R^10a)R^10b as a meaning for R⁸ is selected from H and Ci-C₆-alkyl; R^10b in C(=O)N(R^10a)R^10b as a meaning for R⁸ is selected from H, Ci-C₆-alkyl, C₂- C4-alkynyl, CH₂-CN, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyI, Cs-Ce-halocycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy,

R⁹ is selected from H, Ci-C6-alkyl and Ci-C6-haloalkyl;

R^10a in -N(R^10a)R¹⁰ as a meaning for R⁶ is H;

R¹⁰ in -N(R^10a)R¹⁰ as a meaning for R⁶ is -C(=0)N(R^14a)R¹⁴ or a heteroaromatic ring selected from rings of formulae E-1 , E-2, and E-7 as defined above, wherein R^14a is H and d-Ce-alkyl; and

R^14b is H, Ci-Ce-alkyl, Ci-Ce-haloalkyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, Cs-Ce- halocycloalkyl, CH2-CN, Ci-C4-alkoxy and Ci-C4-haloalkoxy; and

R¹¹ and R¹⁶; independently of each occurrence and independently of each other (also in rings E-1 to E-1 1 ), are selected from halogen, CN, NO2, CrC4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, C3- C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, aminocarbonyl, Ci- C4-alkylaminocarbonyl and di-(Ci-C4-alkyl)-aminocarbonyl; or

two R¹¹ present on the same carbon atom of a saturated heterocyclic ring may form together =0 or =S; or two R¹⁶ present on the same carbon atom of a saturated heterocyclic ring may form together =0 or =S.

In an alternative embodiment of formula I compounds, A is A².

Preferably, R^7a and R^7b in group A² are independently of each other selected from H, CN, Ci- C₄-alkyl and CrC₄-haloalkyl, and more preferably from H, Ci-C₄-alkyl and Ci-C₄-haloalkyl. Even more preferably, one of R^7a and R^7b is H and the other is H or CH3. Specifically, both are H.

In group A², groups R⁵ and R⁶ are preferably defined as outlined above for preferred embodiments.

More preferably, in group A²,

R⁵ is selected from H, Ci-C₄-alkyl, C2-C3-alkynyl, CH2-CN and Ci-C6-alkoxy-methyl- and

preferably from hydrogen and Ci-C₄-alkyl; and

R⁶ is -C(=0)R⁸; wherein R⁸ has one of the above general meanings, or, in particular, one of the below preferred meanings.

More preferably, R⁸ in C(=0)R⁸ as a meaning of the radicals R⁵ and R⁶ of the group A² is selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkyl substituted with one radical R¹³, C2-C₄-alkenyl, C2-C₄-haloalkenyl, C2-C₄-alkynyl, C2-C₄-haloalkynyl, C3-C8- cycloalkyl which is unsubstituted or substituted by CN, or Cs-Cs-halocycloalkyl,

N(R ^0a)R ^0b, C(=O)N(R ^0a)R ^0b, CH=NOR⁹,

phenyl which is unsubstituted or substituted by one or more same or different, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, and a 3-, 4-, 5- or 6-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms O, S, N and C=0 as ring members, wherein S may be oxidized, the heterocyclic ring is unsubstituted or substituted by one or more same or different, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶,

wherein R⁹, R^10a, R^10b, R¹³ and R¹⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings.

R⁹ in CH=NOR⁹ as a meaning of R⁸ in the group C(=0)R⁸ as a meaning of the radicals R⁵ and R⁶ of the group A² is preferably selected from H, Ci-C6-alkyl and Ci-C6-haloalkyl.

R^10a and R¹⁰ in C(=O)N(R^10a)R¹⁰ and N(R^10a)R¹⁰ as a meaning of R⁸ in the group

C(=0)R⁸ as a meaning of the radicals R⁵ and R⁶ of the group A² are, independently of each other, preferably selected from H, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C3-alkenyl, C2-C3-haloalkenyl, C2-C3-alkynyl, C2-C3-haloalkynyl, C3-C6-cycloalkyl which optionally carries a CN substituent, C3- Cs-halocycloalkyI, where the aliphatic and cycloaliphatic moieties are unsubstituted or partially or fully substituted by radicals R¹³; C(=0)NR(^14a)R^14b, phenyl which is unsubstituted or substituted by one or more same or different R¹⁶; and a heteromonocyclic ring selected from rings of formulae E-1 to E-1 1 as defined above. R¹³ in R⁸ in the radicals R⁵ and R⁶ of the group A² is preferably selected from CN, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkyl- thio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, -C(=0)N(R^14a)R^14b, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substituents R¹⁶; and a heterocyclic ring selected from rings of formulae E-1 to E-11 as defined above. R^14a and R^14b in C(=0)NR(^14a)R^14b as a meaning for R^10a and R^10b as well as a meaning for R¹³, independently of each other and independently of each occurrence, are preferably selected from H, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- aloalkynyl, which aliphatic radicals are unsubstituted or substituted by 1 substituent selected from CN, C1-C4- alkoxy, Ci-C4-haloalkoxy, C3-C4-cycloalkyl which may be substituted by 1 CN; and C3-C4- halocycloalkyl;

Cs-Ce-cycloalkyI which is unsubstituted or substituted by 1 CN; and Cs-Cs-halocycloalkyl; and more preferably from H, Ci-C6-alkyl, Ci-C6-haloalkyl, CH₂-CN, C2-C4-alkenyl, C2-C4-alky- nyl, C₃-C6-cycloalkyl, C₃-C6-halocycloalkyl, C₃-C6-cycloalkylmethyl-, Ci-C4-alkoxy and C1-C4- haloalkoxy. Preferably, each R¹⁶ as a substituent on phenyl or heterocyclic rings E-1 to E-1 1 is independently selected from H, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-halo- alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2- C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, aminocarbonyl, Ci-C4-alkylaminocarbonyl and di-(Ci-C4-alkyl)-aminocarbonyl; or

two R¹⁶ present on the same carbon atom of a saturated heterocyclic ring may form together =0 or =S.ln particular, R⁸ in C(=0)R⁸ as a meaning of the radicals R⁵ and R⁶ of the group A² is H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl substituted by one radical R¹³, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl,C3-C8-cycloalkyl which is unsubstituted or substituted by CN, C₃-C₈-halocycloalkyl, N(R^10a)R^10b, C(=O)N(R^10a)R^10b, CH=NOR⁹, phenyl which is unsubstituted or partially or fully substituted by same or different R¹⁶; and a heterocyclic ring selected from rings E-1 to E-1 1 as defined above, wherein

R⁹ is H, d-Ce-alkyl or Ci-C₆-haloalkyl;

R^10a is H, Ci-C₄-alkyl, CrC₄-haloalkyl and C₃-C₆-cycloalkyl, and preferably H and CrC₄-alkyl; R^10b is H, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl which is unsubstituted or substituted by a CN; C(=0)N(R^14a)R^14b; phenyl, which is unsubstituted or partially or fully substituted by R¹⁶; and a heteromonocyclic ring selected from rings E-1 to E-1 1 as defined above;

R¹³ is selected from CN, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio,

Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, -

C(=0)N(R^14a)R¹⁴ , phenyl, which is unsubstituted or partially or fully substituted by R¹⁶; and a heterocyclic ring selected from rings E-1 to E-1 1 as defined above;

R^14a is selected from H and Ci-Ce-alkyl;

R¹⁴ is selected from H, Ci-Ce-alkyl, Ci-C₆-haloalkyl, CH₂-CN, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-

C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkylmethyl-, Ci-C4-alkoxy and C1-C4- haloalkoxy; and

each R¹⁶ as a substituent on phenyl or heterocyclic rings E-1 to E-1 1 is independently

selected from halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, CrC₆-alkylsulfonyl, CrC₆-haloalkylsulfonyl, C₃-C6-cycloalkyl, C₃-C6-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkylcarbonyl, C1-C4- haloalkylcarbonyl, aminocarbonyl, Ci-C4-alkylaminocarbonyl and di-(Ci-C4-alkyl)- aminocarbonyl; or

In an alternative embodiment of formula I compounds, A is A³. Preferably A³ is a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heteromonocyclic ring containing 1 , 2, 3, or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted or substituted by up to 3 R¹¹.

A³ is preferably selected from pyrazoles, oxazoles, thiazoles, and triazoles, which rings are unsubstituted or substituted by R¹¹ , more preferably the rings are selected from 1 -pyrazolyl and 1 ,2,4-triazolyl, which are substituted by (R¹¹)_k.

More preferably A³ is selected from 1-pyrazole, 2-oxazole, 2-thiazole and 1 ,2,4-triazole which rings are unsubstituted or substituted by (R¹¹)k. Particularly A³ is 1-Pyrazolyl, or 1 ,2,4-Triazolyl which rings are unsubstituted or substituted by (R¹¹)k.

Preferably the heterocycle in A³ is unsubstituted. In another embodiment k is 1 or 2.

Preferably, each R¹¹ is independently selected from halogen, CN, NO2, Ci-C4-alkyl, Ci-C₄-ha- loalkyl, Ci-C₄-alkoxy, CrC₄-haloalkoxy, Ci-C₄-alkylthio, Ci-C₄-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C3-C6-cycloalkyl, C3-C6-halo- cycloalkyl, C2-C₄-alkenyl, C2-C₄-haloalkenyl, C2-C₄-alkynyl, C2-C₄-haloalkynyl, Ci-C₄-alkylcarbo- nyl, Ci-C₄-haloalkylcarbonyl, aminocarbonyl, Ci-C₄-alkylaminocarbonyl and di-(Ci-C₄-alkyl)- aminocarbonyl; or two R¹¹ present on the same carbon atom of a saturated or partially unsaturated ring may form together =0 or =S.

Particularyl preferred R¹¹ is selected from halogen, CN, NO2, SCN, SF₅, Ci-Cio-alkyl, C3-C8- cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, which groups are unsubstituted, or partially or fully halogenated.

In one embodiment, B¹ , B² and B³ are CR², wherein R⁴ has one of the above general meanings, or, in particular, one of the below preferred meanings.

Preferably, B¹ and B² are CR², with R² being H, CI or F, and B³ is CCI.

Particularly, B¹ is H or CI, B² is H or F, and B³ is CI.

Preferably, G¹, G², G³ and G⁴ are CR⁴, where R⁴ has one of the above general meanings, or, in particular, one of the below preferred meanings.

In one embodiment, G¹ , G³ and G⁴ are CH and G² is CR⁴, wherein R⁴ has one of the above general meanings, or, in particular, one of the below preferred meanings.

In another embodiment G³ and G⁴ are CH and G¹ and G² together form a five- or

sixmembered saturated or fully unsaturated carbocyclic ring, preferably a sixmembered fully unsaturated carbocyclic ring.

In another embodiment G¹, G² and G⁴ are CH, and G³ is CR⁴, wherein R⁴ together with R^7a forms a -CH₂CH₂- chain.

Preferably, R⁴ is selected from H, halogen, CN, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Cs-Cs-cycloalkyl, C3-C5-halocycloalkyl, C2-C₄-alkenyl, C2-C₄-haloalkenyl, C2-C₄-alkynyl, C2-C₄-haloalkynyl, C1-C4- alkoxy, Ci-C₄-haloalkoxy, Ci-C₄-alkylthio and Ci-C₄-haloalkylthio, and in particular from H, F, CI, Br, CN, CH₃ and CF₃. Preferably, R¹ is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- haloalkoxy-Ci-C4-alkyl, or C(=0)OR¹⁵; more preferably from Ci-C4-alkyl, Ci-C4-haloalkyl and C(=0)OR¹⁵, and particularly preferably from Ci-C₄-haloalkyl and C(=0)OR¹⁵, wherein R¹⁵ is preferably Ci-C4-alkyl. In particular, R¹ is halomethyl, specifically fluoromethyl, such as CH2F, CHF2, and CF3, and is particularly CF3.

If not specified otherwise above, R⁸, R⁹, R^10a, R^10b, R¹¹ , R¹², R¹³, R¹⁵ and R¹⁶ have following preferred meanings: In case R⁸ is a substituent on an alkyl, alkenyl or alkynyl group, it is preferably selected from the group consisting of cyano, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, OR⁹, SR⁹,

C(=O)N(R^10a)R^10b, C(=S)N(R^10a)R^10b, C(=0)OR⁹, phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms N, O, S, wherein N and/or S may be oxidized, as ring members, wherein the heterocyclic ring is unsubstituted or partially or fully substituted by R¹⁶; wherein R⁹, R^10a, R^10b and R¹⁶ have one of the meanings given above or in particular one of the preferred meanings given below.

In case R⁸ is a substituent on an alkyl, alkenyl or alkynyl group, it is even more preferably selected from the group consisting of cyano, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4- alkoxy, Ci-C₄-haloalkoxy, Ci-C₄-alkylthio, Ci-C₄-haloalkylthio, C(=O)N(R^10a)R¹⁰ ,

C(=S)N(R^10a)R¹⁰ , C(=0)OR⁹, phenyl which is unsubstituted or partially or fully substituted by same or different R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms N, O, S, wherein N and/or S may be oxidized, as ring members, which ring is unsubstituted or partially or fully substituted by same or different R¹⁶; wherein R⁹, R^10a, R^10b and R¹⁶ have one of the meanings given above or in particular one of the preferred meanings given below. In particular it is CN, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C(=O)N(R^10a)R¹⁰ , C(=S)N(R^10a)R¹⁰ , C(=0)OR⁹, phenyl which is unsubstituted or partially or fully substituted by same or different R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms N, O, S, wherein N and/or S may be oxidized, as ring members, which ring is unsubstituted or partially or fully substituted by same or different R¹⁶; wherein R⁹, R^10a, R^10b and R¹⁶ have one of the meanings given above or in particular one of the preferred meanings given below.

In case R⁸ is a substituent on a cycloalkyl group, it is preferably selected from the group consisting of cyano, Ci-C₆-alkyl, Ci-C₆-haloalkyl, Ci-C₆-alkoxy-Ci-C₆-alkyl, OR⁹, OSO2R⁹, SR⁹, N(R^10a)R¹⁰ , C(=O)N(R^10a)R¹⁰ , C(=S)N(R^10a)R¹⁰ , -C(=0)OR⁹, phenyl which is unsubstituted or partially or fully substituted by same or different R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms N, O, S, wherein N and/or S may be oxidized, as ring members, which ring is unsubstituted or partially or fully substituted by same or different R¹⁶; where R⁹, R^10a, R^10b and R¹⁶ have one of the meanings given above or in particular one of the preferred meanings given below.

In case R⁸ is a substituent on a cycloalkyl group, it is even more preferably selected from the group consisting of cyano, Ci-C4-alkyl, Ci-C3-haloalkyl, Ci-C4-alkoxy and Ci-C3-haloalkoxy. In particular, R⁸ as a substituent on a cycloalkyl group is selected from cyano, Ci-C4-alkyl and Ci- C3-haloalkyl. In case of R⁸ in a group -C(=0)R⁸, R⁸ is preferably selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, -OR⁹, -SR⁹, - N(R^10a)R^10b, phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms N, O, S, wherein N and/or S may be oxidized,, as ring members, wherein the heterocyclic ring is unsubstituted or partially or fully substituted by same or different R¹⁶;

wherein R⁹, R^10a, R^10b and R¹⁶ have one of the meanings given above or in particular one of the preferred meanings given below.

In case of R⁸ in a group C(=0)R⁸, =C(R⁸)₂, R⁸ is more preferably selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, Ci-C6-alkoxy, d-Ce-haloalkoxy, N(R^10a)R^10b, phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms N, O, S, wherein N and/or S may be oxidized, as ring members, which ring is unsubstituted or partially or fully substituted by same or different R¹⁶; wherein R^10a, R^10b and R¹⁶ have has one of the meanings given above or in particular one of the preferred meanings given below.

Preferably, each R⁹ is independently selected from the group consisting of H, Ci-C6-alkyl, Ci- C6-haloalkyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or hetero- atom groups selected from N, O, S, NO, SO and S0₂, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1 , 2, 3 or 4, preferably 1 or 2, more preferably 1 , radicals R¹⁶, where R¹⁶ has one of the meanings given above or in particular one of the preferred meanings given below.

More preferably, each R⁹ is independently selected from the group consisting of hydrogen, Ci- C6-alkyl, Ci-C6-haloalkyl, phenyl which is unsubstituted or partially or fully substituted by same or different R¹⁶; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S, as ring members, where the heteroaromatic ring is unsubstituted or partially or fully substituted by R¹⁶; where R¹⁶ has one of the meanings given above or in particular one of the preferred meanings given below.

More preferably, R⁹ is H, Ci-C₆-alkyl, Ci-C₆-haloalkyl, Cs-Cs-cycloalkyl, C₃-C₈-cycloalkyl-Ci-C4- alkyl-, C3-Cs-halocycloalkyl, C₂-C6-alkenyl, C₂-C6-haloalkenyl, C₂-C6-alkynyl, or C₂-C6-haloalky- nyl, which groups are unsubstituted, or partially or fully substituted by same or different SO_n-Ci- Ce-alkyl, SO_n-CrC₆-haloalkyl, C(=0)N(R ^4a)R ^4b; or N(R ^0a)R ^0b, or C(=0)OR¹⁵; or a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶, wherein the heterocyclic ring is preferably selected from rings HET.

R^10a and R^10b are, independently of each other, preferably selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C₂-C4-alkenyl, C₂-C4-haloalkenyl, C₂-C4-alkynyl, C₂-C4-haloalkynyl, C₃-C6-cyclo- alkyl, C₃-C6-halocycloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkylaminocar- bonyl, Ci-C4-haloalkylaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, C3-C6-halocycloalkyl- aminocarbonyl, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C₂-C4-alkenyl, C₂-C4-haloalkenyl, C₂-C4-alkynyl, C₂- C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio and Ci-C4-haloalkylthio;

or, R^10a and R^10b, together with the nitrogen atom to which they are bound, form a 5- or 6- membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, wherein the heterocyclic is unsubstituted or substituted by 1 or 2, in particular 1 , substituents selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C₂-C4-haloalkenyl, C₂-C4-alkynyl, C₂-C4-haloalkynyl, C₃-C6-cycloalkyl, C₃-C6-halocycloalkyl, Ci- C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, and Ci-C4-haloalkylthio.

More preferably, R^10a and R^10b are, independently of each other, selected from H, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, and a 3- or 4-membered saturated heterocyclic ring comprising 1 heteroatom or heteroatom group selected from N, O, S, NO, SO and SO2, as ring member, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy or Ci-C4-haloalkoxy; and are specifically, independently of each other, H, Ci-C4-alkyl or Ci-C4-haloalkyl.

Each R¹¹ and each R¹⁶ are independently of each occurrence and independently of each other preferably selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci- C4-alkylsulfonyl and Ci-C4-haloalkylsulfonyl, and more preferably from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy. Each R¹² is preferably selected from Ci-C4-alkyl and is in particular methyl.

In case R¹³ is a substituent on an alkyl, alkenyl or alkynyl group, it is preferably selected from CN, Cs-Cs-cycloalkyl, C₃-C₈-halocycloalkyl, OH, SH, Ci-C₄-alkoxy, Ci-C₄-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci- C4-haloalkylsulfonyl and phenyl which is unsunstituted or substituted by 1 , 2 or 3 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

In case R¹³ is a substituent on a cycloalkyl group, it is preferably selected from CN, Ci-C6-al- kyl, Ci-Ce-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, OH, SH, Ci-C₄-alkoxy, Ci-C₄-halo- alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-al- kylsulfonyl, Ci-C4-haloalkylsulfonyl and phenyl which is unsubstituted or substituted by 1 , 2 or 3 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

In case R¹³ is a substituent on a cycloalkyl group, it is even more preferably selected from halogen, Ci-C4-alkyl, Ci-C3-haloalkyl, Ci-C4-alkoxy and Ci-C3-haloalkoxy. In particular, R¹³ as a substituent on a cycloalkyl group is selected from halogen, Ci-C4-alkyl and Ci-C3-haloalkyl. In case of R¹³ in a group -C(=0)R¹³, -C(=S)R¹³, =C(R ³)₂ or -C(=NR ⁴)R¹³, R⁸ is preferably selected from H, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, OH, SH, Ci-C6-alkoxy, Ci-C6-haloalkoxy and phenyl which may be substituted by 1 , 2 or 3 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

R¹⁴, R^14a and R^14b are, independently of each other, preferably selected from H, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6- cycloalkyl, C3-C6-halocycloalkyl and benzyl, where the phenyl ring in benzyl is optionally substituted 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;

or, R^14a and R^14b, together with the nitrogen atom to which they are bound, form a 5- or 6- membered saturated, partially unsaturated or aromatic heterocyclic ring, which may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, wherein the heterocyclic ring is unsubstituted or substituted by 1 or 2, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy.

More preferably, R¹⁴, R^14a and R^14b are, independently of each other, selected from H, C1-C4- alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and benzyl, where the phenyl ring in benzyl is optionally substituted 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;

or, R^14a and R^14b, together with the nitrogen atom to which they are bound, form a 5- or 6- membered saturated, partially unsaturated or aromatic heterocyclic ring, which may contain 1 or 2 further heteroatoms or heteroatom groups N, O, S, NO, SO or SO2, as ring members, wherein the heterocyclic ring is unsubstituted or substituted by 1 or 2, in particular 1 , substituents halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

Each R¹⁵ is preferably selected from H, Ci-C6-alkyl, Ci-C6-haloalkyl, phenyl, benzyl, pyridyl and phenoxy, which rings are unsubstituted or substituted by 1 , 2 or 3 substituents Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy.

Compounds of formula I.A, wherein R^2a and R³ are both H, and R^2b is F, are a particularly preferred embodiment. Such compounds correspond to formula IA.1 , wherein the variables are as defined and preferred for formula IA, and R^5a is preferably H. R^4A is preferably halogen, such as CI, or Ci-C4-alkyl, such as CH3. In one embodiment R⁶ is Ci-C4-alkyl, preferably ethyl, which is substituted by halogen, cycloalkyl, halocycloalkyl, S(0)_n-CrC2-alkyl, oxo, alkylamino, or haloalkylamino. In another embodiment R⁶ is a 5- or 6-membered heteroaryl group, preferably selected from thietan, oxothietan, dioxothietan, pyrimidin, pyrrolidin, isoxazolidin, bonded ether directly or via a CH2 bridge. The rings are prefereably unsubstituted, or may be substituted by halogen, Ci-C4-alkyl, or oxo. Further preferred embodiments are listed in Table A.

The compounds of general formula I, particularly of formulae IA.1 , IB.1 , Id , ID.1 , and IE.1 , which are indicated in Tables 1 to 167 below, and their stereoisomers, salts, tautomers and N- oxides, represent per se preferred embodiments of the present invention. The meanings for the variables indicated in Tables 1 to 167, and particularly in Tables A, B, and C, resp., below represent embodiments of the invention which are likewise preferred independently of one another and especially in combination.

Table 1 Compounds of formula IA.1 in which R¹ is CF₃, R^4A is F, R^5a is H, and R⁶ for a compound corresponds in each case to one row of Table A

Table 2 Compounds of formula IA.1 in which R¹ is COOCH₃, R^4A is F, R^5a is H, and R⁶ for a compound corresponds in each case to one row of Table A

Table 3 Compounds of formula IA.1 in which R¹ is CF₃, R^4A is F, R^5a is CH₃, and R⁶ for a compound corresponds in each case to one row of Table A

Table 4 Compounds of formula IA.1 in which R¹ is COOCH₃, R^4A is F, R^5a is CH₃, and R⁶ for a compound corresponds in each case to one row of Table A

Table 5 Compounds of formula IA.1 in which R¹ is CF₃, R^4A is CI, R^5a is H, and R⁶ for a

compound corresponds in each case to one row of Table A

Table 6 Compounds of formula IA.1 in which R¹ is COOCH3, R^4A is CI, R^5a is H, and R⁶ for a compound corresponds in each case to one row of Table A

Table 7 Compounds of formula IA.1 in which R¹ is CF₃, R^4A is CI, R^5a is CH₃, and R⁶ for a compound corresponds in each case to one row of Table A

Table 8 Compounds of formula IA.1 in which R¹ is COOCH₃, R^4A is CI, R^5a is CH₃, and R⁶ for a compound corresponds in each case to one row of Table A

Table 9 Compounds of formula IA.1 in which R¹ is CF₃, R^4A is Br, R^5a is H, and R⁶ for a compound corresponds in each case to one row of Table A

Table 10 Compounds of formula IA.1 in which R¹ is COOCH₃, R^4A is Br, R^5a is H, and R⁶ for a compound corresponds in each case to one row of Table A

Table 1 1 Compounds of formula IA.1 in which R¹ is CF₃, R^4A is Br, R^5a is CH₃, and R⁶ for a compound corresponds in each case to one row of Table A

Table 12 Compounds of formula IA.1 in which R¹ is COOCH₃, R^4A is Br, R^5a is CH₃, and R⁶ for a compound corresponds in each case to one row of Table A

Table 13 Compounds of formula IA.1 in which R¹ is CF₃, R^4A is CN, R^5a is H, and R⁶ for a compound corresponds in each case to one row of Table A

Table 14 Compounds of formula IA.1 in which R¹ is COOCH₃, R^4A is CN, R^5a is H, and R⁶ for a compound corresponds in each case to one row of Table A

Table 15 Compounds of formula IA.1 in which R¹ is CF₃, R^4A is CN, R^5a is CH₃, and R⁶ for a compound corresponds in each case to one row of Table A

Table 16 Compounds of formula IA.1 in which R¹ is COOCH₃, R^4A is CN, R^5a is CH₃, and R⁶ for a compound corresponds in each case to one row of Table A

Table 17 Compounds of formula IA.1 in which R¹ is CF₃, R^4A is CH₃, R^5a is H, and R⁶ for a compound corresponds in each case to one row of Table A Table 18 Compounds of formula IA.1 in which R¹ is COOCH₃, R^4A is CH₃, R^5a is H, and R⁶ for a compound corresponds in each case to one row of Table A

Table 19 Compounds of formula IA.1 in which R¹ is CF₃, R^4A is CH₃, R^5a is CH₃, and R⁶ for a compound corresponds in each case to one row of Table A

Table 20 Compounds of formula IA.1 in which R¹ is COOCH₃, R^4A is CH₃, R^5a is CH₃, and R⁶ for a compound corresponds in each case to one row of Table A

Table 21 Compounds of formula IB.1 in which R⁶ for a compound corresponds in each case to one row of Table A

No. R⁶ No. R⁶

A-52 CH₂CH₂CF=CF₂ A-94 3-CH₃-1 ,1 -0₂-thietan-3-yl

A-53 C-C3H5 A-95 CH₂-thietan-3-yl

A-54 I -CN-C-C3H4 A-96 CH₂-(1-oxo-thietan-3-yl)

A-55 1 -(2PY)-c-C₃H₄ A-97 CH₂-(1 ,1-0₂-thietan-3-yl)

A-56 C-C4H7 A-98 tetrahydrothiophen-3-yl

A-57 1 -CN-c-C₄H₆ A-99 1 -oxo-tetrahydrothiophen-3-yl

A-58 3,3-F₂-c-C₄H5 A-100 1 , 1 -0₂-tetrahydrothiophen-3-yl

A-59 C-C5H9 A-101 CH₂-CONH₂

A-60 1 -CN-c-C₅H₈ A-102 C6H5

A-61 c-C₆Hii A-103 pyridin-2-yl

A-62 1 -CN-c-C₆Hio A-104 pyridin-3-yl

A-63 CH₂-c-C₃H₅ A-105 pyridin-4-yl

A-64 CH₂-(1-CN-c-C₃H₄) A-106 pyrimidin-2-yl

A-65 CH₂-(1 -F-c-C₃H₄) A-107 pyrimidin-4-yl

A-66 CH₂-(1-CI-c-C₃H₄) A-108 pyrimidin-5-yl

A-67 CH₂-(1-Br-c-C₃H₄) A-109 thiazol-2-yl

A-68 CH₂-(2,2-F₂-c-C₃H₃) A-1 10 4-CF₃-thiazol-2-yl

A-69 CH₂-(2,2-CI₂-c-C₃H₃) A-1 1 1 oxetan-3-yl

A-70 CH₂-(2,2-Br₂-c-C₃H₃) A-1 12 tetrahydrofuran-2-yl

A-71 CH₂-c-C₄H₇ A-1 13 tetrahydrofuran-3-yl

A-72 CH₂-(1-CN-c-C₄H₆) A-1 14 2-oxotetrahyd rof u ra n-3-y I

A-73 CH₂-(1 -F-c-C₄H₆) A-1 15 2-oxopyrrolidin-3-yl

A-74 CH₂-(1-CI-c-C₄H₆) A-1 16 1 -C H 3— 2-oxopy rrol id i n-3-y I

A-75 CH₂-(2,2-F₂-c-C₄H5) A-1 17 1-C₂F₃-2-oxopyrrolidin-3-yl

A-76 CH₂-(3,3-F₂-c-C₄H5) A-1 18 azetidin-3-yl

A-77 CH₂-(2,2,3,3-F₄-c-C₄H₃) A-1 19 1-acetyl-azetidin-3-yl

A-78 CH₂-(2,2,3,3,4,4-c-C4F₆H) A-120 NH-C₆H₅

A-79 Chb-c-CsHg A-121 NH-pyridin-2-yl

A-80 CH₂-(1 -F-c-C₅H₈) A-122 NH-pyridin-3-yl

A-81 CH₂-(1-CI-c-C₅H₈) A-123 NH-pyridin-4-yl

A-82 CH₂-(1-CN-c-C₅H₈) A-124 N(CH₃)-pyridin-2-yl

A-83 CH₂-(2,2-F₂-c-C₅H₇) A-125 NH-pyrimidin-2-yl

A-84 CH₂-(3,3-F₂-c-C₅H₇) A-126 NH-pyrimidin-4-yl

A-85 CH₂-c-C₆Hii A-127 NH-pyrimidin-5-yl

A-86 CH₂-(1 -F-c-C₆Hio) A-128 CH₂-COOCH₃

A-87 CH₂-(1-CI-c-C₆Hio) A-129 CH₂-COOC₂H₅

A-88 CH₂-(1-CN-c-C₆Hio) A-130 CH₂-CONHCH₃

A-89 thietan-3-yl A-131 CH₂-CONHC₂H₅

A-90 1 -oxo-thietan-3-yl A-132 CH₂-CONHCH₂CHF₂

A-91 1 ,1 -0₂-thietan-3-yl A-133 CH₂-CONHCH₂CF₃

A-92 3-CH₃-thietan-3-yl A-134 CH₂-CONH-c-C₃H₅

A-93 3-CH₃-1-oxo-thietan-3-yl A-135 CH₂-CONHCH(CH₃)₂ No. R⁶ No. R⁶

A-136 CH₂-CONHCH(CF₃)CH₃ A-178 CH₂-thien-3-yl

A-137 CH₂-CONHCH(CF₃)₂ A-179 CH₂-thiazol-2-yl

A-138 CH2-CON HCH2CH2CF3 A-180 CH₂-thiazol-4-yl

A-139 CH2-CON HCH2CN A-181 CH₂-thiazol-5-yl

A-140 CH₂-CONHCH₂CH=CH₂ A-182 CH₂-(2-CI-thiazol-5-yl)

A-141 CH₂-CONHCH₂C≡CH A-183 CH2-isothiazol-3-yl

A-142 CH2-CON(CH₃)CH₂CF3 A-184 CH₂-isothiazol-4-yl

A-143 CH(CH₃)-CONHCH₂CF₃ A-185 CH2-isothiazol-5-yl

A-144 CH₂-CONHCH₂-c-C₃H₅ A-186 CH₂-oxazol-2-yl

A-145 CH₂-CONHCH₂(1 -CN-c-C₃H₄) A-187 CH₂-oxazol-4-yl

A-146 CH₂-CONH-thietan-3-yl A-188 CH2-oxazol-5-yl

A-147 CH2-CON H-1 -oxo-thietan-3-yl A-189 CH2-isoxazol-3-yl

A-148 CH2-CON H-1 , 1 -0₂-thietan-3-yl A-190 CH2-isoxazol-4-yl

A-149 CH2C₆H5 A-191 CH₂-isoxazol-5-yl

A-150 CH₂(2-F-C₆H₅) A-192 CH₂-[1 ,2,3]-thiadiazol-4-yl

A-151 CH₂(3-F-C₆H₅) A-193 CH₂-[1 ,2,3]-thiadiazol-2-yl

A-152 CH₂(4-F-C₆H₅) A-194 CH₂-(1 -CH₃-imidazol-2-yl)

A-153 CH₂(2-CI-C₆H₅) A-195 CH₂-(1 -CH₃-imidazol-4-yl)

A-154 CH₂(3-CI-C₆H₅) A-196 CH₂-(1 -CH₃-imidazol-5-yl)

A-155 CH₂(4-CI-C₆H₅) A-197 CH₂-(1 -CH₃-pyrazol-3-yl)

A-156 CH2-pyridazin-4-yl A-198 CH₂-(2-CH₃-pyrazol-3-yl)

A-157 CH2-tetrahydrofuran-2-yl A-199 CH2-tetrahydrofuran-3-yl

A-158 CH₂-[1 ,2,3]-thiadiazol-5-yl A-200 CH₂-1 ,3-dioxolan-2-yl

A-159 CH₂(2-SCH₃-C₆H₅) A-201 CH(CH₃)-2-pyridyl

A-160 CH₂(3-SCH₃-C₆H₅) A-202 (1 R) CH(CH₃)-2-pyridyl

A-161 CH₂(4-SCH₃-C₆H₅) A-203 (1 S) CH(CH₃)-2-pyridyl

A-162 CH2(2-S02CH₃-C₆H₅) A-204 CONH2

A-163 CH2(3-S02CH₃-C₆H₅) A-205 CON HCH3

A-164 CH2(4-S02CH₃-C₆H₅) A-206 CON HCH2CH3

A-165 CH2-pyridin-2-yl A-207 CON HCH2CH2CH3

A-166 CH2-pyridin-3-yl A-208 CONH-C-C3H5

A-167 CH₂-(6-CI-pyridin-3-yl) A-209 CON HCH2-C-C3H5

A-168 CH2-pyridin-4-yl A-210 CONHC₆H₅

A-169 CH₂-(5-CI-pyridin-2-yl) A-21 1 CONHCH₂C₆H₅

A-170 CH₂-(6-CF₃-pyridin-2-yl) A-212 NHCONHCH3

A-171 CH₂-(6-CF₃-pyridin-3-yl) A-213 NHCONHC₂H₅

A-172 CH2-pyrimidin-2-yl A-214 NHCONHCH2CH2CH3

A-173 CH2-pyrimidin-4-yl A-215 NHCONHCH(CH₃)₂

A-174 CH2-pyrimidin-5-yl A-216 NHCONHCH2CF3

A-175 CH2-pyridazin-3-yl A-217 NHCONHCH2CHF2

A-176 CH2-pyrazin-2-yl A-218 NHCONHCH(CH₃)CF₃

A-177 CH₂-thien-2-yl A-219 NHCONHCH(CF₃)₂ No. R⁶ No. R⁶

A-220 NHCONHCH2CN isoxazolidin-4-yl

A-221 NHCONHCH₂CH=CH₂ 2-[CH₂(2-F-C₆H₄)]-3-oxo-

A-250

A-222 NHCONHCH₂CH≡CH isoxazolidin-4-yl

A-223 NHCO-NH-C-C3H5 2-[CH₂(4-OCH₃-C₆H₄)]-3-oxo-

A-251

A-224 NHCONH(1 -CN-c-C₃H₄) isoxazolidin-4-yl

A-225 NHCONH-C-C4H7 2-[CH₂(2-CF₃-C₆H₄)]-3-oxo-

A-252

A-226 NHCONH-(1 -CN-c-C₄H₆) isoxazolidin-4-yl

A-227 NHCONHCH2-C-C3H4) 2-[CH₂(2-OCF₃-C₆H₄)]-3-oxo-

A-253

A-228 NHCONHCH₂-(1 -CN-c-C₃H₄) isoxazolidin-4-yl

A-229 CH=NOCH₃ 2-(CH₂-2PY)-3-oxo-isoxazolidin-

A-254

A-230 CH=NOCH₂CF₃ 4-yl

A-231 3-oxo-isoxazolidin-4-yl 2-(CH₂-3PY)-3-oxo-isoxazolidin-

A-255

A-232 2-CH3-3-oxo-isoxazolidin-4-yl 4-yl

A-233 2-C₂H₅-3-oxo-isoxazolidin-4-yl 2-[CH₂-(2-CI-5PY]-3-oxo-

A-256

A-234 2-C₃H₇-3-oxo-isoxazolidin-4-yl isoxazolidin-4-yl

A-235 2-C₄H9-3-oxo-isoxazolidin-4-yl 2-[CH₂-(1 -CH3-I H-imidazol-4-

A-257

2-(but-2-yl)-3-oxo-isoxazolidin-4- yl)]-3-oxo-isoxazolidin-4-yl

A-236 2-[CH₂-(furan-2-yl)]-3-oxo- yi A-258

2-CH₂CH₂CH₂Br-3-oxo- isoxazolidin-4-yl

A-237

isoxazolidin-4-yl 2-[(2-thiophen-2'-yl)-eth-1 -yl]-3-

A-259

2-CH₂CH₂F-3-oxo-isoxazolidin- oxo-isoxazolidin-4-yl

A-238

4-yl 2-[2-(indol-3'-yl)-eth-1-yl]-3-oxo-

A-260

2-CH₂CHF₂-3-oxo-isoxazolidin- isoxazolidin-4-yl

A-239

4-yl 2- [CH₂-(1 H-benzimidazol-2-yl)]-

A-261

2-CH₂CF₃-3-oxo-isoxazolidin-4- 3- oxo-isoxazolidin-4-yl

A-240 2-[CH₂-(oxetan-2-yl)]-3-oxo- yi A-262

2-CH₂CH₂CF₃-3-oxo- isoxazolidin-4-yl

A-241

isoxazolidin-4-yl 2-[CH₂-(THF-2-yl)]-3-oxo-

A-263

2-CH₂CH₂OCH₃-3-oxo- isoxazolidin-4-yl

A-242

isoxazolidin-4-yl 2-[(2-[1 ',3']dioxolan-2'-yl)-eth-1 -

A-264

2-CH(CH₃)CH₂OCH₃-3-oxo- yl]-3-oxo-isoxazolidin-4-yl

A-243

isoxazolidin-4-yl 2-[(2-morpholin-4'-yl)-eth-1yl]-3-

A-265

A-244 2-c-C₄H₇-3-oxo-isoxazolidin-4-yl oxo-isoxazolidin-4-yl

2-(2-CH₃-cyclohex-1 -yl)-3-oxo- 2-[(2-benzo[1 ',3']dioxol-5'-yl)-

A-245 A-266

isoxazolidin-4-yl eth-1-yl]-3-oxo-isoxazolidin-4-yl

2-(CH₂C6H5)-3-oxo-isoxazolidin- 2-[(2,3-dihydro-benzo[1 ,4]dioxin-

A-246

4-yl A-267 6-yl)-methyl]-3-oxo-isoxazolidin-

2-[CH(CH₃)C₆H₅]-3-oxo- 4-yl

A-247

isoxazolidin-4-yl 2-(2-CI-C₆H₄)-3-oxo-

A-268

2-(C₂H₄C₆H₅)-3-oxo- isoxazolidin-4-yl

A-248

isoxazolidin-4-yl 2-(3-F-C₆H₄)-3-oxo-isoxazolidin-

A-269

A-249 2-[CH₂(3-CI-C₆H₄)]-3-oxo- 4-yl No. R⁶ No. R⁶

2-(2-CH₃-C₆H₄)-3-oxo- 2-( 1 -oxo-th ietan-3-yl)-3-oxo-

A-270 A-283

isoxazolidin-4-yl isoxazolidin-4-yl

2-(2-CI-6-CH₃-C₆H₃)-3-oxo- 2-(1 ,1-dioxo-thietan-3-yl)-3-oxo-

A-271 A-284

isoxazolidin-4-yl isoxazolidin-4-yl

2-(2-CF₃-C₆H₄)-3-oxo- 2-(3-CH₃-thietan-3-yl)-3-oxo-

A-272 A-285

isoxazolidin-4-yl isoxazolidin-4-yl

2-(2,4-(OCH₃)₂-C₆H₃)-3-oxo- 2-(oxetan-3-yl)-3-oxo-

A-273 A-286

isoxazolidin-4-yl isoxazolidin-4-yl

2-(3-CH₃-pyrid-2-yl)-3-oxo- 2-(tetrahydropyran-4-yl)-3-oxo-

A-274 A-287

isoxazolidin-4-yl isoxazolidin-4-yl

2-[1 ,3-(CH₃)₂-1 H-pyrazol-5-yl]-3- A-288 NHCH₃

A-275

oxo-isoxazolidin-4-yl A-289 NHCH2CH3

2-(4-CH₃-thiazol-2-yl)-3-oxo- A-290 CH2CH₂SCH₂CH=CH2

A-276

isoxazolidin-4-yl A-291 CH2CH₂S(0)CH₂CH=CH2

2-(5-CH₃-thiazol-2-yl)-3-oxo- A-292 CH2CH₂SCH₂C≡CH

A-277

isoxazolidin-4-yl A-293 CH₂CH₂S(0)CH₂C≡CH

2-(quinolin-2-yl)-3-oxo- A-294 CH₂CH₂SCH₂-c-C₃H5

A-278

isoxazolidin-4-yl A-295 CH₂CH₂S(0)CH₂-c-C₃H5

2-(quinolin-5-yl)-3-oxo- A-296 CONHCH₂CF₃

A-279

isoxazolidin-4-yl A-297 CONHCH₂CH₂CF₃

2-(benzothiazol-6-yl)-3-oxo- A-298 CH₂-thietan-2-yl

A-280

isoxazolidin-4-yl A-299 CH₂-(1-oxo-thietan-2-yl)

2-(4-CH₃-benzothiazol-2-yl)-3- A-300 CH₂-(1 ,1-dioxo-thietan-2-yl)

A-281

oxo-isoxazolidin-4-yl pyridinyl

2-(thietan-3-yl)-3-oxo- = tetrahydrofuranyl

A-282

isoxazolidin-4-yl

Compounds of formula I.B1 , wherein R⁶ is Ci-C₄-alkyl, preferably ethyl, which is substituted by halogen, cycloalkyl, halocycloalkyl, S(0)_n-Ci-C₂-alkyl, oxo, alkylamino, or haloalkylamino constitute a preferred embodiment. In another embodiment R⁶ is a 5- or 6-membered heteroaryl group, preferably selected from thietan, oxothietan, dioxothietan, pyrimidin, pyrrolidin, isoxazolidin, bonded ether directly or via a CH₂ bridge. The rings are prefereably unsubstituted, or may be substituted by halogen, Ci-C₄-alkyl, or oxo. Further preferred embodiments are listed in Table A.

Table 22 Compounds of formula Id in which R^4A is F, and A³ for a compound corresponds in each case to one row of Table B Table 23 Compounds of formula IC.1 in which R^4A is CI, and A³ for a compound corresponds in each case to one row of Table B

Table 24 Compounds of formula IC.1 in which R^4A is Br, and A³ for a compound corresponds in each case to one row of Table B

Table 25 Compounds of formula IC.1 in which R^4A is CN, and A³ for a compound corresponds in each case to one row of Table B

Table 26 Compounds of formula IC.1 in which R^4A is CH₃, and A³ for a compound

corresponds in each case to one row of Table B Table B

Compounds of formula I.D1 , wherein R⁹ is Ci-C6-alkyl, Ci-C6-haloalkyl, C₃-C8-cycloalkyl, C₃- C8-cycloalkyl-Ci-C4-alkyl-, C₃-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, SO_n-Ci-C6- alkyl, SO_n-Ci-C6-haloalkyl, with n being 0, 1 , or 2, are particularly preferred embodiments. Further preferred embodiments are listed in Table 27.

Table 27 Compounds of formula ID.1 in which R⁹ for a compound corresponds in each case to one row of Table C

o. R⁹ No. R⁹

C-12 CHF₂ C-54 2,5-F2-CeH₃

C-13 CFs C-55 2,6-F2-CeH₃

C-14 CH2CHF2 C-56 3,4-F₂-C₆H₃

C-15 CH2CF3 C-57 3,5-F2-CeH₃

C-16 CF2CF3 C-58 2-CI-C₆H₄

C-17 CH2CH2CF3 C-59 3-CI-C6H₄

C-18 CH(CH₃)CF₃ C-60 4-CI-C₆H₄

C-19 CH(CF₃)₂ C-61 2-OCH₃-C₆H₄

C-20 CF(CF₃)₂ C-62 3-OCH₃-C₆H₄

C-21 CH₂CN C-63 4-OCH₃-C₆H₄

C-22 CH=CH₂ C-64 pyridin-2-yl

C-23 CH₂CH=CH₂ C-65 pyridin-3-yl

C-24 C≡CH C-66 pyridin-4-yl

C-25 CH₂C≡CH C-67 4-CI-pyridin-3-yl

C-26 CN C-68 pyrimidin-2-yl

C-27 CH=CHF C-69 CH₂OCH₃

C-28 CH=CF₂ C-70 CH₂OCH₂CH₃

C-29 CF=CF₂ C-71 CH₂OCF₃

C-30 c-C₃H₅ C-72 CH₂SCH₃

C-31 1-F-c-C₃H₄ C-73 CH₂SCH₂CH₃

C-32 1-CN-c-C₃H₄ C-74 CH₂SCF₃

C-33 C-C4H7 C-75 CH₂S(0)CH₃

C-34 1-F-c-C₄H₆ C-76 CH₂S(0)CH₂CH₃

C-35 1-CN-c-C₄H₆ C-77 CH₂S(0)CF₃

C-36 cyclobut-1-enyl C-78 CH₂S0₂CH₃

C-37 CH₂-c-C₃H₅ C-79 CH₂S02CH₂CH₃

C-38 CH₂-(1 -CN-c-C₃H₄) C-80 CH₂S0₂CF₃

C-39 CH2-C-C4H7 C-81 CH(CH₃)S0₂CH₃

C-40 CH₂-(1 -CN-c-C₄H₆) C-82 C(CH₃)₂S0₂CH₃

C-41 oxetan-2-yl C-83 CH₂N(CH₃)₂

C-42 oxetan-3-yl C-84 CH₂CH₂N(CH₃)₂

C-43 tetrahydrofuran-2-yl C-85 NHCH₃

C-44 tetrahydrofuran-3-yl C-86 NHCH2CH3

C-45 thietan-3-yl C-87 NHCH2CHF2

C-46 1-oxo-thietan-3-yl C-88 NHCH2CF3

C-47 1 ,1-dioxo-thietan-3-yl C-89 NHCH₂CH=CH₂

C-48 C₆H5 C-90 NHCH₂C≡CH

C-49 2-F-C₆H₄ C-91 NHCH2CN

C-50 3-F-C6H₄ C-92 NH-C-C3H5

C-51 4-F-C₆H₄ C-93 NH-(1-CN-c-C₃H₄)

C-52 2,3-F2-C6H₃ C-94 NHCH2-C-C3H5

C-53 2,4-F₂-C₆H₃ C-95 NHCH₂-(1-CN-c-C₃H₄) No. R⁹ No. R⁹

C-96 C(0)NHCH₃ C-1 18 NHC(0)N HCH₂CF₃

C-97 C(0)NHCH₂CH₃ C-1 19 NHC(0)N HCH₂CH=CH₂

C-98 C(0)NHCH₂CHF₂ C-120 NHC(0)N HCH₂C≡CH

C-99 C(0)NHCH₂CF₃ C-121 NHC(0)N HCH₂CN

C-100 C(0)NHCH₂CH=CH₂ C-122 NHC(0)NH-c-C₃H₅

C-101 C(0)NHCH₂C≡CH C-123 NHC(0)NH-(1 -CN-c-C₃H₄)

C-102 C(0)NHCH₂CN C-124 NHC(0)N HCH₂-c-C₃H₅

C-103 C(0)NH-c-C₃H₅ C-125 NHC(0)N HCH₂-(1 -CN-c-C₃H₄)

C-104 C(0)NH-(1 -CN-c-C₃H₄) C-126 CH=N-OCH₃

C-105 CH₂C(0)NHCH₃ C-127 CH=N-OCH₂CH₃

C-106 CH₂C(0)NHCH₂CHF₂ C-128 CH=N-OCH₂CHF₂

C-107 CH₂C(0)NHCH₂CF₃ C-129 CH=N-OCH₂CF₃

C-108 CH₂C(0)NHCH₂CH=CH₂ C-130 CH=N-OCH₂CH=CH₂

C-109 CH₂C(0)NHCH₂C≡CH C-131 CH=N-OCH₂C≡CH

C-1 10 CH₂C(0)NHCH₂CN C-132 CH=N-OCH₂CN

C-1 1 1 CH₂C(0)NH-c-C₃H₅ C-133 CH=N-0-c-C₃H₅

C-1 12 CH₂C(0)NH-(1 -CN-c-C₃H₄) C-134 CH=N-0-(1 -CN-c-C₃H₄)

C-1 13 CH₂C(0)NHCH₂-c-C₃H₅ C-135 CH=N-0-(2,2-F₂-c-C₃H₃)

C-1 14 CH₂C(0)NHCH₂(1 -CN-c-C₃H₄) C-136 CH=N-0-CH₂-c-C₃H₅

C-1 15 NHC(0)NHCH₃ C-137 CH=N-0-CH₂-(1 -CN-c-C₃H₄)

C-1 16 NHC(0)NHCH₂CH₃ C-138 CH=N-0-CH₂-(2,2-F₂-c-C₃H₃)

C-1 17 NHC(0)NHCH₂

Compounds of formula I . E1 , wherein R¹ is CF₃, COOCH₃, R^4A is CN, F, CI, Br, CH₃, R⁶ and R^7a are both H, and R⁹ is Ci-C6-alkyl, Ci-C6-haloalkyl, C₃-C8-cycloalkyl, C₃-C8-cycloalkyl-Ci-C₄-alkyl, C₃-C₈-halocycloalkyl, C₂-C6-alkenyl, C₂-C6-haloalkenyl, SO_n-Ci-C6-alkyl, SO_n-Ci-C6-haloalkyl, phenyl, which is unsubstituted, or partially or fully substituted by same or different R¹⁶; or 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶. Further preferred embodiments are listed in Table C.

Table 28 Compounds of formula I E.1 in which R¹ is CF₃, R^4A is F, R⁶ is H, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 29 Compounds of formula I E.1 in which R¹ is COOCH₃, R^4A is F, R⁶ is H, R^7a is H, R⁹ for a compound corresponds in each case to one row of Table C

Table 30 Compounds of formula I E.1 in which R¹ is CF₃, R^4A is CI, R⁶ is H, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 31 Compounds of formula I E.1 in which R¹ is COOCH₃, R^4A is CI, R⁶ is H, R^7a is H, R⁹ for a compound corresponds in each case to one row of Table C Table 32 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is Br, R⁶ is H, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 33 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is Br, R⁶ is H, R^7a is H, and

R⁹ for a compound corresponds in each case to one row of Table C

Table 34 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CN, R⁶ is H, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 35 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CN, R⁶ is H, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 36 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CH₃, R⁶ is H, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 37 Compounds of formula IE.1 in which R¹ is COOCH3, R^4A is CH₃, R⁶ is H, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 38 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is F, R⁶ is H, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 39 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is F, R⁶ is H, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 40 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CI, R⁶ is H, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 41 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CI, R⁶ is H, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 42 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is Br, R⁶ is H, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 43 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is Br, R⁶ is H, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 44 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CN, R⁶ is H, R^7a is CH₃, and

R⁹ for a compound corresponds in each case to one row of Table C

Table 45 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CN, R⁶ is H, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 46 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CH₃, R⁶ is H, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 47 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CH₃, R⁶ is H, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 48 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is F, R⁶ is CH₃, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 49 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is F, R⁶ is CH₃, R^7a is H, R⁹ for a compound corresponds in each case to one row of Table C

Table 50 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CI, R⁶ is CH₃, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 51 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CI, R⁶ is CH₃, R^7a is H, R⁹ for a compound corresponds in each case to one row of Table C

Table 52 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is Br, R⁶ is CH₃, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 53 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is Br, R⁶ is CH₃, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C Table 54 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CN, R⁶ is CH₃, R^7a is H, and

R⁹ for a compound corresponds in each case to one row of Table C

Table 55 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CN, R⁶ is CH₃, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 56 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CH₃, R⁶ is CH₃, R^7a is H, and

R⁹ for a compound corresponds in each case to one row of Table C

Table 57 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CH₃, R⁶ is CH₃, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 58 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is F, R⁶ is CH₃, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 59 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is F, R⁶ is CH₃, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 60 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CI, R⁶ is CH₃, R^7a is CH₃, and

R⁹ for a compound corresponds in each case to one row of Table C

Table 61 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CI, R⁶ is CH₃, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 62 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is Br, R⁶ is CH₃, R^7a is CH₃, and

R⁹ for a compound corresponds in each case to one row of Table C

Table 63 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is Br, R⁶ is CH₃, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 64 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CN, R⁶ is CH₃, R^7a is CH₃, and

R⁹ for a compound corresponds in each case to one row of Table C

Table 65 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CN, R⁶ is CH₃, R^7a is

CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 66 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CH₃, R⁶ is CH₃, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 67 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CH₃, R⁶ is CH₃, R^7a is

CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 68 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is F, R⁶ is C₂H₅, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 69 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is F, R⁶ is C2H5, R^7a is H,

R⁹ for a compound corresponds in each case to one row of Table C

Table 70 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CI, R⁶ is C2H5, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 71 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CI, R⁶ is C2H5, R^7a is H,

R⁹ for a compound corresponds in each case to one row of Table C

Table 72 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is Br, R⁶ is C₂H₅, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 73 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is Br, R⁶ is C2H5, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 74 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CN, R⁶ is C2H5, R^7a is H, and

R⁹ for a compound corresponds in each case to one row of Table C

Table 75 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CN, R⁶ is C₂H₅, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C Table 76 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CH₃, R⁶ is C₂H₅, R^7a is H, and

R⁹ for a compound corresponds in each case to one row of Table C

Table 77 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CH₃, R⁶ is C2H5, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 78 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is F, R⁶ is C2H5, R^7a is CH₃, and

R⁹ for a compound corresponds in each case to one row of Table C

Table 79 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is F, R⁶ is C₂H₅, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 80 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CI, R⁶ is C2H5, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 81 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CI, R⁶ is C2H5, R^7a is

CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 82 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is Br, R⁶ is C2H5, R^7a is CH₃, and

R⁹ for a compound corresponds in each case to one row of Table C

Table 83 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is Br, R⁶ is C2H5, R^7a is

CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 84 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CN, R⁶ is C2H5, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 85 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CN, R⁶ is C2H5, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 86 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CH₃, R⁶ is C₂H₅, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 87 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CH₃, R⁶ is C2H5, R^7a is

CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 88 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is F, R⁶ is n-C₃H₇, R^7a is H, and

R⁹ for a compound corresponds in each case to one row of Table C

Table 89 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is F, R⁶ is n-C₃H₇, R^7a is H,

R⁹ for a compound corresponds in each case to one row of Table C

Table 90 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CI, R⁶ is n-C₃H₇, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 91 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CI, R⁶ is n-C₃H₇, R^7a is H,

R⁹ for a compound corresponds in each case to one row of Table C

Table 92 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is Br, R⁶ is n-C₃H₇, R^7a is H, and

R⁹ for a compound corresponds in each case to one row of Table C

Table 93 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is Br, R⁶ is n-C₃H₇, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 94 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CN, R⁶ is n-C₃H₇, R^7a is H, and

R⁹ for a compound corresponds in each case to one row of Table C

Table 95 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CN, R⁶ is n-C₃H₇, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 96 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CH₃, R⁶ is n-C₃H₇, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 97 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CH₃, R⁶ is n-C₃H₇, R^7a is

H, and R⁹ for a compound corresponds in each case to one row of Table C Table 98 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is F, R⁶ is n-C₃H₇, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 99 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is F, R⁶ is n-C₃H₇, R^7a is

CH3, and R⁹ for a compound corresponds in each case to one row of Table C

Table 100 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CI, R⁶ is n-C₃H₇, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 101 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CI, R⁶ is n-C₃H₇, R^7a is

CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 102 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is Br, R⁶ is n-C₃H₇, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 103 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is Br, R⁶ is n-C₃H₇, R^7a is

CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 104 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CN, R⁶ is n-C₃H₇, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 105 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CN, R⁶ is n-C₃H₇, R^7a is

CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 106 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CH₃, R⁶ is n-C₃H₇, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 107 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CH₃, R⁶ is n-C₃H₇, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 108 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is F, R⁶ is CH₂CN, R^7a is H, and

R⁹ for a compound corresponds in each case to one row of Table C

Table 109 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is F, R⁶ is CH₂CN, R^7a is H,

R⁹ for a compound corresponds in each case to one row of Table C

Table 1 10 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CI, R⁶ is CH₂CN, R^7a is H, and

R⁹ for a compound corresponds in each case to one row of Table C

Table 1 1 1 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CI, R⁶ is CH₂CN, R^7a is

H, R⁹ for a compound corresponds in each case to one row of Table C

Table 1 12 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is Br, R⁶ is CH₂CN, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 1 13 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is Br, R⁶ is CH₂CN, R^7a is

H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 1 14 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CN, R⁶ is CH₂CN, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 1 15 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CN, R⁶ is CH₂CN, R^7a is

H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 1 16 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CH₃, R⁶ is CH₂CN, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 1 17 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CH₃, R⁶ is CH₂CN, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 1 18 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is F, R⁶ is CH₂CN, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 1 19 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is F, R⁶ is CH₂CN, R^7a is

CH₃, and R⁹ for a compound corresponds in each case to one row of Table C Table 120 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CI, R⁶ is CH₂CN, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 121 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CI, R⁶ is CH₂CN, R^7a is

CH3, and R⁹ for a compound corresponds in each case to one row of Table C

Table 122 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is Br, R⁶ is CH₂CN, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 123 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is Br, R⁶ is CH₂CN, R^7a is

CH3, and R⁹ for a compound corresponds in each case to one row of Table C

Table 124 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CN, R⁶ is CH₂CN, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 125 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CN, R⁶ is CH₂CN, R^7a is

CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 126 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CH₃, R⁶ is CH₂CN, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 127 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CH₃, R⁶ is CH₂CN, R^7a is

CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 128 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is F, R⁶ is CH₂C≡CH, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 129 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is F, R⁶ is CH₂C≡CH, R^7a is H, R⁹ for a compound corresponds in each case to one row of Table C

Table 130 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CI, R⁶ is CH₂C≡CH, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 131 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CI, R⁶ is CH₂C≡CH, R^7a is H, R⁹ for a compound corresponds in each case to one row of Table C

Table 132 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is Br, R⁶ is CH₂C≡CH, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 133 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is Br, R⁶ is CH₂C≡CH, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 134 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CN, R⁶ is CH₂C≡CH, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 135 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CN, R⁶ is CH₂C≡CH, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 136 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CH₃, R⁶ is CH₂C≡CH, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 137 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CH₃, R⁶ is CH₂C≡CH, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 138 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is F, R⁶ is CH₂C≡CH, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 139 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is F, R⁶ is CH₂C≡CH, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 140 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CI, R⁶ is CH₂C≡CH, R^7a is

CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 141 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CI, R⁶ is CH₂C≡CH, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C Table 142 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is Br, R⁶ is CH₂C≡CH, R^7a is

CH3, and R⁹ for a compound corresponds in each case to one row of Table C

Table 143 Compounds of formula IE.1 in which R¹ is COOCH3, R^4A is Br, R⁶ is CH₂C≡CH, R^7a is CH3, and R⁹ for a compound corresponds in each case to one row of Table C

Table 144 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CN, R⁶ is CH₂C≡CH, R^7a is

CH3, and R⁹ for a compound corresponds in each case to one row of Table C

Table 145 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CN, R⁶ is CH₂C≡CH, R^7a is CH3, and R⁹ for a compound corresponds in each case to one row of Table C

Table 146 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CH₃, R⁶ is CH₂C≡CH, R^7a is CH3, and R⁹ for a compound corresponds in each case to one row of Table C

Table 147 Compounds of formula IE.1 in which R¹ is COOCH3, R^4A is CH₃, R⁶ is CH₂C≡CH, R^7a is CH3, and R⁹ for a compound corresponds in each case to one row of Table C

Table 148 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is F, R⁶ is CH₂OCH₃, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 149 Compounds of formula IE.1 in which R¹ is COOCH3, R^4A is F, R⁶ is CH₂OCH₃, R^7a is

H, R⁹ for a compound corresponds in each case to one row of Table C

Table 150 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CI, R⁶ is CH₂OCH₃, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 151 Compounds of formula IE.1 in which R¹ is COOCH3, R^4A is CI, R⁶ is CH₂OCH₃, R^7a is H, R⁹ for a compound corresponds in each case to one row of Table C

Table 152 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is Br, R⁶ is CH₂OCH₃, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 153 Compounds of formula IE.1 in which R¹ is COOCH3, R^4A is Br, R⁶ is CH₂OCH₃, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 154 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CN, R⁶ is CH₂OCH₃, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 155 Compounds of formula IE.1 in which R¹ is COOCH3, R^4A is CN, R⁶ is CH₂OCH₃, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 156 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CH₃, R⁶ is CH₂OCH₃, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 157 Compounds of formula IE.1 in which R¹ is COOCH3, R^4A is CH₃, R⁶ is CH₂OCH₃, R^7a is H, and R⁹ for a compound corresponds in each case to one row of Table C

Table 158 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is F, R⁶ is CH₂OCH₃, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 159 Compounds of formula IE.1 in which R¹ is COOCH3, R^4A is F, R⁶ is CH₂OCH₃, R^7a is

CH3, and R⁹ for a compound corresponds in each case to one row of Table C

Table 160 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CI, R⁶ is CH₂OCH₃, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 161 Compounds of formula IE.1 in which R¹ is COOCH3, R^4A is CI, R⁶ is CH₂OCH₃, R^7a is CH3, and R⁹ for a compound corresponds in each case to one row of Table C

Table 162 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is Br, R⁶ is CH₂OCH₃, R^7a is CH₃, and R⁹ for a compound corresponds in each case to one row of Table C

Table 163 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is Br, R⁶ is CH₂OCH₃, R^7a is CH3, and R⁹ for a compound corresponds in each case to one row of Table C Table 164 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CN, R⁶ is CH₂OCH₃, R^7a is

CH3, and R⁹ for a compound corresponds in each case to one row of Table C

Table 165 Compounds of formula IE.1 in which R¹ is COOCH3, R^4A is CN, R⁶ is CH2OCH3, R^7a is CH3, and R⁹ for a compound corresponds in each case to one row of Table C

Table 166 Compounds of formula IE.1 in which R¹ is CF₃, R^4A is CH₃, R⁶ is CH2OCH3, R^7a is

CH3, and R⁹ for a compound corresponds in each case to one row of Table C

Table 167 Compounds of formula IE.1 in which R¹ is COOCH₃, R^4A is CH₃, R⁶ is CH₂OCH₃, R^7a is CH3, and R⁹ for a compound corresponds in each case to one row of Table C Among the above compounds preference is given to compounds of formula IA selected from A-1 to A-6, A-9, A-1 1 , A-12, A-17, A-18, A-22, A-26 to A-31 , A-41 to A-45, A-53 to a-57, A-59, A-63 to A-65, A-71 to A-73, A-89 to A-97, A-103 to A-109, A-1 1 1 , A-121 to A-123, A-125 to A- 127, A-130 to A-134, A-139, A-165, A-166, A-172, A-175, A-176, A-179 to A-181 , A-183 to A- 193, A-213, A-216, A-229, A-231 to A-233, A-240, and A-298 to A-300 of Tables 1 , 5, 9, 13, and 17; compounds of formula IC selected from B-4 and B-10 of Table 25; compounds of formulae ID and IE selected from C-2 to C8, C-10, C-14, C-15, C-21 , C-30 to C-35, C-37 to C-42, C-45 to C-47, C-69 to C-82, C-126, and C-127 of Tables 27, 28, 30, 32, 34, and 36.

Due to their excellent activity, the compounds of the present invention, being particulary of formulae IA, IB, IC, ID, and IE, may be used for controlling invertebrate pests.

The present invention also relates to a mixture of at least one compound of the present invention, being particulary of formulae IA, IB, IC, ID, and IE, with at least one mixing partner as defined herein after. Preferred are binary mixtures of one compound of the present invention as component I with one mixing partner as defined herein after as component II. Preferred weight ratios for such binary mixtures are from 5000:1 to 1 :5000, preferably from 1000:1 to 1 :1000, more preferably from 100:1 to 1 :100, particularly preferably from 10:1 to 1 :10. In such binary mixtures, components I and II may be used in equal amounts, or an excess of component I, or an excess of component II may be used.

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

The following list M of pesticides, grouped and numbered according the Mode of Action Classification of the Insecticide Resistance Action Committee (IRAC), together with which the compounds of the present invention can be used and with which potential synergistic effects might be produced, is intended to illustrate the possible combinations, but not to impose any limitation:

M.1 Acetylcholine esterase (AChE) inhibitors from the class of: M.1A carbamates, for example aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofu- ran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or from the class of M.1 B organophosphates, for example acephate, azamethiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, 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, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion;

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

M.3 Sodium channel modulators from the class of M.3A pyrethroids, for example acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopente- nyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpro- pathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imipro- thrin, meperfluthrin,metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralo- methrin and transfluthrin; or M.3B sodium channel modulators such as DDT or methoxychlor; M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class of M.4A neonicotinoids, for example acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiaclo- prid and thiamethoxam; or the compounds M.4A.2: (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-ni- tro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1 -[(6-Chloropyridin-3-yl)methyl]-7- methyl-8-nitro-5-propoxy-1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridine; or from the class M.4B nicotine;

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

M.6 Chloride channel activators from the class of avermectins and milbemycins, for example abamectin, emamectin benzoate, ivermectin, lepimectin or milbemectin;

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

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

M.9 Selective homopteran feeding blockers, for example M.9B pymetrozine, or M.9C flonicamid;

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

M.1 1 Microbial disruptors of insect midgut membranes, for example bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. israelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus

thuringiensis subsp. kurstakiand bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1 ; M.12 Inhibitors of mitochondrial ATP synthase, for example M.12A diafenthiuron, or M.12B organotin miticides such as azocyclotin, cyhexatin or fenbutatin oxide, or M.12C propargite, or M.12D tetradifon;

M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient, for example chlorfenapyr, DNOC or sulfluramid;

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

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

M.16 Inhibitors of the chitin biosynthesis type 1 , as for example buprofezin;

M.17 Moulting disruptors, Dipteran, as for example cyromazine;

M.18 Ecdyson receptor agonists such as diacylhydrazines, for example methoxyfenozide, tebufenozide, halofenozide, fufenozide or chromafenozide;

M.19 Octopamin receptor agonists, as for example amitraz;

M.20 Mitochondrial complex III electron transport inhibitors, for example M.20A

hydramethylnon, or M.20B acequinocyl, or M.20C fluacrypyrim;

M.21 Mitochondrial complex I electron transport inhibitors, for example M.21 A METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, or M.21 B rotenone;

M.22 Voltage-dependent sodium channel blockers, for example M.22A indoxacarb, or M.22B metaflumizone, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methylphenyl)-2-[(4- chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide;

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

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

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

M.28 Ryanodine receptor-modulators from the class of diamides, as for example flubendi- amide, chlorantraniliprole (rynaxypyr®), cyantraniliprole (cyazypyr®), tetraniliprole, or the phthalamides M.28.1 : (R)-3-Chlor-N1-{2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluormethyl)ethyl]phe- nyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid and M.28.2: (S)-3-Chloro-N1 -{2-methyl-4- [1 ,2,2,2 - tetrafluor-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthal- amid, or the compound M.28.3: 3-bromo-N-{2-bromo-4-chloro-6-[(1 -cyclopropylethyl)carbamo- yl]phenyl}-1-(3-chlorpyridin-2-yl)-1 H-pyrazole-5-carboxamide (proposed ISO name: cyclanili- prole), or the compound M.28.4: methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chlorpyridin-2-yl)-1 H- pyrazol-5-yl]carbonyl}amino)benzoyl]-1 ,2-dimethylhydrazinecarboxylate; or a compound

M.28.5a) to M.28.5d) and M.28.5h) to M.28.5I): M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4- sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carbox- amide; M.28.5b) N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2- (3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5c) N-[4-chloro-2-[(di-2- propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridy fluoromethyl)pyrazole-3-carboxamide; M.28.5d) N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfa- nylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxami M.28.5h) N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2- pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5i) N-[2-(5-Amino-1 ,3,4-thiadiazol-2- yl)-4-chloro-6-methylphenyl]-3-bromo-1 -(3-chloro-2-pyridinyl)-1 H-pyrazole-5-carboxamide; M.28.5j) 3-Chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1 -cyano-1 -methylethyl)amino]car- bonyl]phenyl]-1 H-pyrazole-5-carboxamide; M.28.5k) 3-Bromo-N-[2,4-dichloro-6-(methylcarb- amoyl)phenyl]-1 -(3,5-dichloro-2-pyridyl)-1 H-pyrazole-5-carboxamide; M.28.5I) N-[4-Chloro-2- [[(1 ,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1 -(3-cN

1 H-pyrazole-5-carboxamide; or

M.28.6: cyhalodiamide; or;

M.29. insecticidal active compounds of unknown or uncertain mode of action, as for example afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, bifenazate, broflanilide, bro- mopropylate, chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluen- sulfone, fluhexafon, fluopyram, flupyradifurone, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim, or M.29.3: 1 1 -(4- chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-1 1 -en-10-one, or M.29.4: 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2- one, or M.29.5: 1 -[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)- 1 H-1 ,2,4-triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582); or M.29.6, selected from M.29.6a) to M.29.6k): M.29.6a) (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridyli- dene]-2,2,2-trifluoro-acetamide; M.29.6b) (E/Z)-N-[1 -[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyri- dylidene]-2,2,2-trifluoro-acetamide; M.29.6c) (E/Z)-2,2,2-trifluoro-N-[1-[(6-fluoro-3-pyri- dyl)methyl]-2-pyridylidene]acetamide; M.29.6d) (E/Z)-N-[1-[(6-bromo-3-pyridyl)methyl]-2-pyridyli- dene]-2,2,2-trifluoro-acetamide; M.29.6e) (E/Z)-N-[1 -[1-(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]- 2,2,2-trifluoro-acetamide; M.29.6f) (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-di- fluoro-acetamide; M.29.6g) (E/Z)-2-chloro-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2- difluoro-acetamide; M.29.6h) (E/Z)-N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-tri- fluoro-acetamide; M.29.6i) (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pen- tafluoro-propanamide.); M.29.6j) N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro- thioacetamide; or M.29.6k) N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-N'- isopropyl-acetamidine; or

M.29.8: fluazaindolizine; or

M.29.9. a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxo- thietan-3-yl)benzamide; or M.29.9.b): fluxametamide; or

M.29.10: 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole; or a compound selected from the group of M.29.1 1 , wherein the compound is selected from M.29.1 1 b) to M.29.1 1 p): M.29.1 1 .b) 3-(benzoylmethylamino)-N-[2-bromo-4-[1 ,2,2,3,3,3-hexa- fluoro-1 -(trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide; M.29.1 1.c) 3- (benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]-benzamide; M.29.1 1 .d) N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoro- methyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.29.1 1.e) N-[3-[[[2-bromo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]ami- no]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide; M.29.1 1.f) 4-fluoro-N-[2-fluoro-3-[[[2- iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]car^^ nyl]-N-methyl-benzamide; M.29.1 1 .g) 3-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(tri- fluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide^ M.29.1 1.h) 2-chloro-N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6-(trifluoro- methyl)phenyl]amino]carbonyl]phenyl]- 3-pyridinecarboxamide; M.29.1 1 .i) 4-cyano-N-[2-cyano- 5-[[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2- methyl-benzamide; M.29.1 1.j) 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4- [1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide; M.29.1 1 .k) N-[5- [[2-chloro-6-cyano-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cy- ano-phenyl]-4-cyano-2-methyl-benzamide; M.29.1 1.1) N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro- 1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benz- amide; M.29.1 1 .m) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)pro- pyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.29.1 1 .n) 4-cyano-N-[2- cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamo- yl]phenyl]-2-methyl-benzamide; M.29.1 1.o) 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,2-tetra- fluoro-1 -(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.29.1 1 .p) N-[5- [[2-bromo-6-chloro-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano phenyl]-4-cyano-2-methyl-benzamide; or

a compound selected from the group of M.29.12, wherein the compound is selected from

M.29.12a) to M.29.12m): M.29.12.a) 2-(1 ,3-Dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; M.29.12.b) 2-[6-[2-(5-Fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; M.29.12.c) 2-[6-[2- (3-Pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; M.29.12. d) N-Methylsulfonyl-6-[2-(3-pyridyl)thi- azol-5-yl]pyridine-2-carboxamide; M.29.12. e) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyri- dine-2-carboxamide; M.29.12.f) N-Ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-pro- panamide; M.29.12. g) N-Methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide; M.29.12.h) N,2-Dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide;

M.29.12. i) N-Ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide; M.29.12.j) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propanamide; M.29.12.k) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methylthio-propanamide;

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

M.29.12. m) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-3-methylthio-propanamide; or

M.29.14a) 1 -[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M.29.14b) 1 -[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol; or

M.29.16a) 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.29.16b) 1 - (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16c) N,5- dimethyl-N-pyridazin-4-yl-1 -(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4-carboxamide; M.29.16d) 1 - [1 -(1 -cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;

M.29.16e) N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carbox- amide; M.29.16f) 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16g) 1-[1 -(1 -cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxami- de; M.29.16h) N-methyl-1 -(2-fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-car- boxamide; M.29.16i) 1 -(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide; or M.29.16j) 1 -(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4- carboxamide, or

M.29.17 a compound selected from the compounds M.29.17a) to M.29.17j): M.29.17a) N-(1 - methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M.29.17b) N-cyclopropyl-2-(3-pyridi- nyl)-2H-indazole-4-carboxamide; M.29.17c) N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carbox- amide; M.29.17d) 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide; M.29.17e) 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide; M.29.17f) methyl 2- [[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate; M.29.17g) N-[(2,2-difluorocyclo- propyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide; M.29.17h) N-(2,2-difluoropropyl)-2- (3-pyridinyl)-2H-indazole-5-carboxamide; Μ.29.17Ϊ) 2-(3-pyridinyl )-N-(2-pyrimidinylmethyl )-2H- indazole-5-carboxamide; M.29.17j) N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole- 5-carboxamide, or

M.29.18 a compound selected from the compounds M.29.18a) to M.29.18d): M.29.18a) N-[3- chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfanyl)propanamide; M.29.18b) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfinyl)propanamide;

M.29.18c) N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfanyl]-N- ethyl-propanamide; M.29.18d) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopro- pyl)methylsulfinyl]-N-ethyl-propanamide; or

M.29.19 sarolaner, or M.29.20 lotilaner.

The commercially available compounds of the group M listed above may be found in The Pesticide Manual, 16th Edition, C. MacBean, British Crop Protection Council (2013) among other publications. The online Pesticide Manual is updated regularly and is accessible through http://bcpcdata.com/pesticide-manual.html.

Another online data base for pesticides providing the ISO common names is

http://www.alanwood.net/pesticides.

The M.4 cycloxaprid is known from WO2010/069266 and WO201 1/069456, M.4A.2, also to be named as guadipyr, is known from WO2013/003977, and the M.4A.3 (approved as

paichongding in China) is known from WO2007/101369. M.22B.1 is described in CN10171577 and M.22B.2 in CN102126994. The phthalamides M.28.1 and M.28.2 are both known from WO2007/101540. The anthranilamide M.28.3 is described in WO2005/077934. The hydrazide M.28.4 is described in WO2007/043677. The anthranilamides M.28.5a) to M.28.5d) and

M.28.5h) are described in WO 2007/006670, WO2013/024009 and WO2013/024010, the anthranilamide Μ.28.5Ϊ) is described in WO201 1/085575, M.28.5j) in WO2008/134969, M.28.5k) in US201 1/046186 and M.28.5I) in WO2012/034403. The diamide M.28.6 can be found in WO 2012/034472. The spiroketal-substituted cyclic ketoenol M.29.3 is known from WO2006/089633 and the biphenyl-substituted spirocyclic ketoenol M.29.4 from WO2008/06791 1. The triazoyl- phenylsulfide M.29.5 is described in WO2006/043635, and biological control agents on the basis of bacillus firmus are described in WO2009/124707. The compounds M.29.6a) to M.29.6i) listed under M.29.6 are described in WO2012/029672, and M.29.6j) and M.29.6k) in WO 2013/129688. The nematicide M.29.8 is known from WO2013/055584. The isoxazoline

M.29.9.a) is described in WO2013/050317. The isoxazoline M.29.9.b) is described in

WO2014/126208. The pyridalyl-type analogue M.29.10 is known from WO2010/060379. The carboxamides broflanilide and M.29.1 1.b) to M.29.1 1.h) are described in WO2010/018714, and the carboxamides M.29.1 1 i) to M.29.1 1 .p) in WO2010/127926. The pyridylthiazoles M.29.12.a) to M.29.12.C) are known from WO2010/006713, M.29.12.d) and M.29.12.e) are known from WO2012/000896, and M.29.12.f) to M.29.12.m) from WO2010/129497. The compounds M.29.14a) and M.29.14b) are known from WO2007/101369. The pyrazoles M.29.16.a) to M.29.16h) are described in WO2010/034737, WO2012/084670, and WO2012/143317, resp., and the pyrazoles M.29.16i) and M.29.16j) are described in US 61/891437. The pyridinyl- indazoles M.29.17a) to M.29.17.j) are described in WO2015/038503. The pyridylpyrazoles M.29.18a) to M.29.18d) are described in US2014/0213448. The isoxazoline M.29.19 is described in WO2014/036056. The isoxazoline M.29.20 is known from WO2014/090918.

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

A) Respiration inhibitors

Inhibitors of complex III at Q₀ site (e. g. strobilurins): azoxystrobin (A.1 .1 ), coumethoxy- strobin (A.1 .2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenamin- strobin (A.1 .6), fenoxystrobin/flufenoxystrobin (A.1 .7), fluoxastrobin (A.1 .8), kresoxim-methyl (A.1 .9), mandestrobin (A.1 .10), metominostrobin (A.1 .1 1 ), orysastrobin (A.1 .12), picoxy. strobin (A.1 .13), pyraclostrobin (A.1 .14), pyrametostrobin (A.1 .15), pyraoxystrobin (A.1.16), trifloxystro- bin (A.1 .17), 2-(2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2- methoxyimino-N-methyl-acetamide (A.1.18), pyribencarb (A.1 .19), triclopyricarb/chlorodincarb (A.1 .20), famoxadone (A.1 .21 ), fenamidone (A.1.21 ), methyl-/V-[2-[(1 ,4-dimethyl-5-phenyl-pyra- zol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1.22), 1-[3-chloro-2-[[1-(4-chlorophenyl)- 1 H-pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one (A.1.23), 1-[3-bromo-2-[[1 -(4-chloro- phenyl)pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one (A.1.24), 1 -[2-[[1 -(4-chloro- phenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (A.1.25), 1-[2-[[1 -(4- chlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one (A.1 .26), 1 -[2-[[1- (2,4-dichlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one (A.1.27), 1- [2-[[4-(4-chlorophenyl)thiazol-2-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (A.1.28), 1-[3-chloro-2-[[4-(p-tolyl)thiazol-2-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one (A.1.29), 1-[3- cyclopropyl-2-[[2-methyl-4-(1 -methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-tetrazol-5- one (A.1 .30), 1 -[3-(difluoromethoxy)-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phe- nyl]-4-methyl-tetrazol-5-one (A.1.31 ), 1-methyl-4-[3-methyl-2-[[2-methyl-4-(1-methylpyrazol-3- yl)phenoxy]methyl]phenyl]tetrazol-5-one (A.1.32), 1-methyl-4-[3-methyl-2-[[1-[3-(trifluoro- methyl)phenyl]-ethylideneamino]oxymethyl]phenyl]tetrazol-5-one (A.1 .33), (Z;2£)-5-[1-(2,4- dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-/V,3-dimethyl-pent-3-enamide (A.1.34), (Z,2E)- 5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-/V,3-dimethyl-pent-3-enamide (A.1 .35), (^2£)-5-[1-(4-chloro-2-fluoro-phenyl)pyrazol-3-yl]oxy-2-methoxyimino-/V,3-dimethyl-pent-3- enamide (A.1 .36),

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

- inhibitors of complex II (e. g. carboxamides): benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.14), penthiopyrad (A.3.15), sedaxane (A.3.16), tecloftalam (A.3.17), thifluzamide (A.3.18), N-(4'-trifluoromethylthiobiphenyl-2-yl)- 3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide (A.3.19), N-(2-(1 ,3,3-trimethyl-butyl)- phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide (A.3.20), 3-(difluoromethyl)-1-methyl- N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.21 ), 3-(trifluoromethyl)-1-methyl-N- (1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.22), 1 ,3-dimethyl-N-(1 ,1 ,3-trimethyl- indan-4-yl)pyrazole-4-carboxamide (A.3.23), 3-(trifluoromethyl)-1 ,5-dimethyl-N-(1 ,1 ,3-trimethyl- indan-4-yl)pyrazole-4-carboxamide (A.3.24), 1 ,3,5-trimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyra- zole-4-carboxamide (A.3.25), N-(7-fluoro-1 ,1 ,3-trimethyl-indan-4-yl)-1 ,3-dimethyl-pyrazole-4- carboxamide (A.3.26), N-[2-(2,4-dichlorophenyl)-2-methoxy-1 -methyl-ethyl]-3-(difluoromethyl)-1- methyl-pyrazole-4-carboxamide (A.3.27);

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

- C14 demethylase inhibitors (DMI fungicides): triazoles: azaconazole (B.1 .1 ), bitertanol (B.1 .2), bromuconazole (B.1 .3), cyproconazole (B.1.4), difenoconazole (B.1 .5), diniconazole (B.1 .6), diniconazole-M (B.1.7), epoxiconazole (B.1 .8), fenbuconazole (B.1 .9), fluquinconazole (B.1 .10), flusilazole (B.1.1 1 ), flutriafol (B.1.12), hexaconazole (B.1 .13), imibenconazole (B.1.14), ipconazole (B.1 .15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole (B.1.20), penconazole (B.1.21 ), propiconazole (B.1.22), prothioconazole

(B.1 .23), simeconazole (B.1 .24), tebuconazole (B.1.25), tetraconazole (B.1 .26), triadimefon (B.1 .27), triadimenol (B.1.28), triticonazole (B.1 .29), uniconazole (B.1 .30), 1-[ eA(2¾3 5)-3-(2- chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1 H-[1 ,2,4]triazolo (B.1 .31 ), 2- [reA(2^3 )-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[1 ,2,4]triazole-3-thiol (B.1 .32), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1 ,2,4-triazol-1-yl)pentan-2-ol (B.1.33), 1-[4- (4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1 ,2,4-triazol-1-yl)ethanol (B.1.34), 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1-yl)butan-2-ol (B.1 .35), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1 -(1 ,2,4-triazol-1-yl)butan-2-ol (B.1.36), 2-[4-(4-chloro- phenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1 ,2,4-triazol-1 -yl)butan-2-ol (B.1.37), 2-[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol (B.1.38), 2-[2-chloro- 4-(4-chlorophenoxy)phenyl]-3-methyl-1 -(1 ,2,4-triazol-1-yl)butan-2-ol (B.1.39), 2-[4-(4-chloro- phenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 ,2,4-triazol-1-yl)pentan-2-ol (B.1.40), 2-[4-(4-fluoro- phenoxy)-2-(trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1 -yl)propan-2-ol (B.1.41 ), 2-[2-chloro-4-(4- chlorophenoxy)phenyl]-1-(1 ,2,4-triazol-1 -yl)pent-3-yn-2-ol (B.1 .51 ); imidazoles: imazalil (B.1.42), pefurazoate (B.1.43), prochloraz (B.1.44), triflumizol (B.1 .45); pyrimidines, pyridines and pipera- zines: fenarimol (B.1.46), nuarimol (B.1 .47), pyrifenox (B.1.48), triforine (B.1 .49), [3-(4-chloro-2- fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.50);

Delta 14-reductase inhibitors: aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8);

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

C) Nucleic acid synthesis inhibitors

phenylamides or acyl amino acid fungicides: benalaxyl (C.1.1 ), benalaxyl-M (C.1 .2), kiralaxyl (C.1.3), metalaxyl (C.1 .4), metalaxyl-M (mefenoxam, C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);

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

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

D) Inhibitors of cell division and cytoskeleton

tubulin inhibitors, such as benzimidazoles, thiophanates: benomyl (D1.1 ), carbendazim

(D1.2), fuberidazole (D1.3), thiabendazole (D1.4), thiophanate-methyl (D1.5);

triazolopyrimidines: 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]tri- azolo[1 ,5-a]pyrimidine (D1 .6);

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

E) Inhibitors of amino acid and protein synthesis

methionine synthesis inhibitors (anilino-pyrimidines): cyprodinil (E.1 .1 ), mepanipyrim (E.1 .2), pyrimethanil (E.1.3);

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

F) Signal transduction inhibitors

MAP / histidine kinase inhibitors: fluoroimid (F.1 .1 ), iprodione (F.1 .2), procymidone (F.1.3), vinclozolin (F.1 .4), fenpiclonil (F.1.5), fludioxonil (F.1 .6);

G protein inhibitors: quinoxyfen (F.2.1 );

G) Lipid and membrane synthesis inhibitors

Phospholipid biosynthesis inhibitors: edifenphos (G.1 .1 ), iprobenfos (G.1 .2), pyrazophos (G.1 .3), isoprothiolane (G.1 .4);

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

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

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

H) Inhibitors with Multi Site Action

inorganic active substances: Bordeaux mixture (H.1 .1 ), copper acetate (H.1 .2), copper hydroxide (H.1.3), copper oxychloride (H.1.4), basic copper sulfate (H.1.5), sulfur (H.1.6);

thio- and dithiocarbamates: ferbam (H.2.1 ), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);

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

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

I) Cell wall synthesis inhibitors

inhibitors of glucan synthesis: validamycin (1.1.1 ), polyoxin B (1.1 .2);

melanin synthesis inhibitors: pyroquilon (1.2.1 ), tricyclazole (I.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil (I.2.5);

J) Plant defence inducers

acibenzolar-S-methyl (J.1.1 ), probenazole (J.1 .2), isotianil (J.1.3), tiadinil (J.1.4), prohexadione-calcium (J.1 .5); phosphonates: fosetyl (J.1 .6), fosetyl-aluminum (J.1.7), phosphorous acid and its salts (J.1 .8), potassium or sodium bicarbonate (J.1.9);

K) Unknown mode of action

bronopol (K.1 .1 ), chinomethionat (K.1.2), cyflufenamid (K.1.3), cymoxanil (K.1.4), dazomet (K.1 .5), debacarb (K.1.6), diclomezine (K.1.7), difenzoquat (K.1.8), difenzoquat-methylsulfate (K.1 .9), diphenylamin (K.1.10), fenpyrazamine (K.1 .1 1 ), flumetover (K.1 .12), flusulfamide (K.1 .13), flutianil (K.1 .14), methasulfocarb (K.1.15), nitrapyrin (K.1.16), nitrothal-isopropyl (K.1 .18), oxathiapiprolin (K.1.19), tolprocarb (K.1.20), oxin-copper (K.1.21 ), proquinazid

(K.1 .22), tebufloquin (K.1 .23), tecloftalam (K.1.24), triazoxide (K.1.25), 2-butoxy-6-iodo- 3-propylchromen-4-one (K.1.26), 2-[3,5-bis(difluoromethyl)-1 H-pyrazol-1-yl]-1 -[4-(4-{5-[2-(prop- 2-yn-1-yloxy)phenyl]-4,5-dihydro-1 ,2-oxazol-3-yl}-1 ,3-thiazol-2-yl)piperidin-1 -yl]ethanone (K.1 .27), 2-[3,5-bis(difluoromethyl)-1 H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yl- oxy)phenyl]-4,5-dihydro-1 ,2-oxazol-3-yl}-1 ,3-thiazol-2-yl)piperidin-1 -yl]ethanone (K.1.28), 2-[3,5- bis(difluoromethyl)-1 H-pyrazol-1-yl]-1 -[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5- dihydro-1 ,2-oxazol-3-yl}-1 ,3-thiazol-2-yl)piperidin-1-yl]ethanone (K.1 .29), N-(cyclopropyl- methoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide (K.1 .30), N'- (4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine (K.1 .31 ), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine (K.1.32), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N- ethyl-N-methyl formamidine (K.1.33), N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl- propoxy)-phenyl)-N-ethyl-N-methyl formamidine (K.1 .34), methoxy-acetic acid 6-tert-butyl-8- fluoro-2,3-dimethyl-quinolin-4-yl ester (K.1.35), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin- 3-yl]-pyridine (K.1.36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (pyrisoxazole) (K.1.37), N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide (K.1.38), 5-chloro-1 -(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole (K.1.39), 2-(4-chloro- phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide, ethyl

(Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1 .40), picarbutrazox (K.1.41 ), pentyl N-[6-[[(Z)- [(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1 .42), 2-[2- [(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol (K.1.43), 2-[2-fluoro-6-[(8-flu- oro-2-methyl-3-quinolyl)oxy]phen-yl]propan-2-ol (K.1 .44), 3-(5-fluoro-3,3,4,4-tetramethyl-3,4- dihydroisoquinolin-1 -yl)quinoline (K.1.45), 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1 - yl)quinoline (K.1 .46), 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline

(K.1 .47), 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1 ,4-benzoxazepine (K.1 .48).

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

The fungicides described by lUPAC nomenclature, their preparation and their pesticidal activity is also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031 ;

EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ; EP-A 532 022; EP-A 1 028 125;

EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197;

DE 10021412; DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ;

WO 01/56358; WO 02/22583; WO 02/40431 ; WO 03/10149; WO 03/1 1853; WO 03/14103;

WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491 ; WO 04/49804;

WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721 ; WO 05/87772;

WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 1 1/028657, WO2012/168188, WO 2007/006670, WO 201 1/77514; W013/047749, WO

10/069882, WO 13/047441 , WO 03/16303, WO 09/90181 , WO 13/007767, WO 13/010862,

WO 13/127704, WO 13/024009, WO 13/024010 and WO 13/047441 , WO 13/162072,

WO 13/092224, WO 1 1/135833). The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of the present invention or a mixture thereof.

An agrochemical composition comprises a pesticidally effective amount of a compound of the present invention or a mixture thereof. The term "pesticidally effective amount" is defined below. The compounds of the present invention or the mixtures thereof can be converted into customary types of agro-chemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for

composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Mono-graph No. 2, 6th Ed. May 2008, CropLife International. The compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

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

Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil frac- tions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclo-'hexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch;

fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

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

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl- sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyhnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethox- ylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol eth- oxylates.

Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are homo- or copolymers of

vinylpyrrolidone, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the present invention on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

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

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

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

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

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

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

Examples for composition types and their preparation are:

i) Water-soluble concentrates (SL, LS)

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

ii) Dispersible concentrates (DC)

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

iii) Emulsifiable concentrates (EC)

15-70 wt% of a compound I according to the invention and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100 wt% water- insoluble organic solvent (e.g. aromatic hydrocarbon). Dilution with water gives an emulsion. iv) Emulsions (EW, EO, ES)

5-40 wt% of a compound I according to the invention and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into up to 100 wt% water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.

v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt% of a compound I according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active sub-stance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added. vi) Water-dispersible granules and water-soluble granules (WG, SG)

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

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

50-80 wt% of a compound I according to the invention are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substance.

viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt% of a compound I according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. car- boxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

ix) Microemulsion (ME)

5-20 wt% of a compound I according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alkohol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.

x) Microcapsules (CS)

An oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g.

methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radi- cal initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylme- thene-4,4'-diisocyanate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the for- mation of a polyurea microcapsule. The monomers amount to 1-10 wt%. The wt% relate to the total CS composition,

xi) Dustable powders (DP, DS)

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

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

xiii) Ultra-low volume liquids (UL)

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

The compositions types i) to xi) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1 -1 wt% col- orants.

The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active sub-stance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

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

The user applies the composition according to the invention usually from a predosage de-vice, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

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

In a further embodiment, either individual components of the composition according to the in- vention or partially premixed components, e. g. components comprising compounds of the present invention and/or mixing partners as defined above, may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.

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

The compounds of the present invention are suitable for use in protecting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, from attack or infestation by animal pests. Therefore, the present invention also relates to a plant protection method, which comprises contacting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of a compound of the present invention. The compounds of the present invention are also suitable for use in combating or controlling animal pests. Therefore, the present invention also relates to a method of combating or controlling animal pests, which comprises contacting the animal pests, their habitat, breeding ground, or food supply, or the crops, plants, plant propagation materials, such as seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesticidally effective amount of a compound of the present invention.

The compounds of the present invention are effective through both contact and ingestion. Furthermore, the compounds of the present invention can be applied to any and all

developmental stages, such as egg, larva, pupa, and adult.

The compounds of the present invention can be applied as such or in form of compositions comprising them as defined above. Furthermore, the compounds of the present invention can be applied together with a mixing partner as defined above or in form of compositions comprising said mixtures as defined above. The components of said mixture can be applied simultaneously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture "in situ" on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.

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

Suitable application methods include inter alia soil treatment, seed treatment, in furrow application, and foliar application. Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection. Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting. In furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrow with seeds, applying the pesticidally active compound to the furrow, and closing the furrow. Foliar application refers to the application of the pesticidally active compound to plant foliage, e.g. through spray equipment. For foliar applications, it can be advantageous to modify the behavior of the pests by use of pheromones in combination with the compounds of the present invention. Suitable pheromones for specific crops and pests are known to a skilled person and publicly available from databases of pheromones and

semiochemicals, such as http://www.pherobase.com.

As used herein, the term "contacting" includes both direct contact (applying the

compounds/compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus, i.e. habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest is growing or may grow, of the animal pest or plant).

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

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

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

geranium/pelargoniums, pansies and impatiens), shrubs, broad-leaved trees (e.g. poplar) or evergreens, e.g. conifers; eucalyptus; turf; lawn; grass such as grass for animal feed or ornamental uses. Preferred plants include potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.

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

Plants, which have been modified by mutagenesis or genetic engineering, and are of particular commercial importance, include alfalfa, rapeseed (e.g. oilseed rape), bean, carnation, chicory, cotton, eggplant, eucalyptus, flax, lentil, maize, melon, papaya, petunia, plum, poplar, potato, rice, soybean, squash, sugar beet, sugarcane, sunflower, sweet pepper, tobacco, tomato, and cereals (e.g. wheat), in particular maize, soybean, cotton, wheat, and rice. In plants, which have been modified by mutagenesis or genetic engineering, one or more genes have been mutagenized or integrated into the genetic material of the plant. The one or more mutagenized or integrated genes are preferably selected from pat, epsps, crylAb, bar, cryl Fa2, cry1 Ac, cry34Ab1 , cry35AB1 , cry3A, cryF, cry1 F, mcry3a, cry2Ab2, cry3Bb1 , cry1A.105, dfr, barnase, vip3Aa20, barstar, als, bxn, bp40, asnl , and ppo5. The mutagenesis or integration of the one or more genes is performed in order to improve certain properties of the plant. Such properties, also known as traits, include abiotic stress tolerance, altered growth/yield, disease resistance, herbicide tolerance, insect resistance, modified product quality, and pollination control. Of these properties, herbicide tolerance, e.g. imidazolinone tolerance, glyphosate tolerance, or glufosinate tolerance, is of particular importance. Several plants have been rendered tolerant to herbicides by mutagenesis, for example Clearfield® oilseed rape being tolerant to

imidazolinones, e.g. imazamox. Alternatively, genetic engineering methods have been used to render plants, such as soybean, cotton, corn, beets and oil seed rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate). Furthermore, insect resistance is of importance, in particular lepidopteran insect resistance and coleopteran insect resistance. Insect resistance is typically achieved by modifying plants by integrating cry and/or vip genes, which were isolated from Bacillus thuringiensis (Bt), and code for the respective Bt toxins. Genetically modified plants with insect resistance are comercially available under trade names including WideStrike®, Bollgard®, Agrisure®, Herculex®, YieldGard®, Genuity®, and Intacta®. Plants may be modified by mutagenesis or genetic engineering either in terms of one property (singular traits) or in terms of a combination of properties (stacked traits). Stacked traits, e.g. the combination of herbicide tolerance and insect resistance, are of increasing importance. In general, all relevant modified plants in connection with singular or stacked traits as well as detailed information as to the mutagenized or integrated genes and the respective events are available from websites of the organizations "International Service for the Acquisition of Agri-biotech Applications (ISAAA)" (http://www.isaaa.org/gmapprovaldatabase) and "Center for Environmental Risk Assessment (CERA)" (http://cera-gmc.org/GMCropDatabase).

It has surprisingly been found that the pesticidal activity of the compounds of the present invention may be enhanced by the insecticidal trait of a modified plant. Furthermore, it has been found that the compounds of the present invention are suitable for preventing insects to become resistant to the insecticidal trait or for combating pests, which already have become resistant to the insecticidal trait of a modified plant. Moreover, the compounds of the present invention are suitable for combating pests, against which the insecticidal trait is not effective, so that a complementary insecticidal activity can advantageously be used.

The term "plant propagation material" refers to all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.

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

In general, "pesticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various

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

In the case of soil treatment, in furrow application or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m², preferably from 0.001 to 20 g per 100 m².

For use in treating crop plants, e.g. by foliar application, the rate of application of the active ingredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to 40 g per hectare, or 40 to 50 g per hectare. The compounds of the present invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling's roots and shoots against soil pests and foliar insects. The present invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and/or after

pregermination with a compound of the present invention. The protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling's shoots from piercing and sucking insects, chewing insects and nematodes.

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

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

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

geranium/pelargoniums, pansies and impatiens.

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

Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having

pregerminated the latter. Preferably, the formulations are applied such that germination is not included.

The active substance concentrations in ready-to-use formulations, which may be obtained after two-to-tenfold dilution, are preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40 % by weight.

In a preferred embodiment a FS formulation is used for seed treatment. Typically, a FS formulation may comprise 1 -800 g/l of active ingredient, 1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.

Especially preferred FS formulations of the compounds of the present invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient, from 0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g. 1 to 40 % by weight of a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.

In the treatment of seed, the application rates of the compounds of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.

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

The compounds of the present invention may also be used for improving the health of a plant. Therefore, the present invention also relates to a method for improving plant health by treating a plant, plant propagation material and/or the locus where the plant is growing or is to grow with an effective and non-phytotoxic amount of a compound of the present invention.

As used herein "an effective and non-phytotoxic amount" means that the compound is used in a quantity which allows to obtain the desired effect but which does not give rise to any phytotoxic symptom on the treated plant or on the plant grown from the treated propagule or treated soil.

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

"Plant health" is defined as a condition of the plant and/or its products which is determined by several aspects alone or in combination with each other such as yield (for example increased biomass and/or increased content of valuable ingredients), quality (for example improved content or composition of certain ingredients or shelf life), plant vigour (for example improved plant growth and/or greener leaves ("greening effect"), tolerance to abiotic (for example drought) and/or biotic stress (for example disease) and production efficiency (for example, harvesting efficiency, processability).

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

The compounds of the invention are also suitable for use against non-crop insect pests. For use against said non-crop pests, compounds of the present invention can be used as bait composition, gel, general insect spray, aerosol, as ultra-low volume application and bed net (impregnated or surface applied). Furthermore, drenching and rodding methods can be used.

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

The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). The bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature (e.g. http://www.pherobase.com), and are known to those skilled in the art.

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

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

The oil spray formulations differ from the aerosol recipes in that no propellants are used. For use in spray compositions, the content of active ingredient is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.

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

Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of the present invention and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder.

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

Customary application rates in the protection of materials are, for example, from 0.001 g to 2000 g or from 0.01 g to 1000 g of active compound per m² treated material, desirably from 0.1 g to 50 g per m². Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and/or insecticide. The compounds of the the present invention are especially suitable for efficiently combating animal pests such as arthropods, gastropods and nematodes including but not limited to:

insects from the order of Lepidoptera, for example Achroia grisella, Acleris spp. such as A. fimbriana, A. gloverana, A. variana; Acrolepiopsis assectella, Acronicta major, Adoxophyes spp. such as A. cyrtosema, A. orana; Aedia leucomelas, Agrotis spp. such as A. exclamationis, A. fucosa, A. ipsilon, A. orthogoma, A. segetum, A. subterranea; Alabama argillacea, Aleurodicus dispersus, Alsophila pometaria, Ampelophaga rubiginosa, Amyelois transitella, Anacampsis sarcitella, Anagasta kuehniella, Anarsia lineatella, Anisota senator/a, Antheraea pernyi, Anti- carsia (=Thermesia) spp. such as A. gemmatalis; Apamea spp., Aproaerema modiceiia, Archips spp. such as A. argyrospila, A. fuscocupreanus, A. rosana, A. xyloseanus; Argyresthia conju- gella, Argyroploce spp., Argyrotaenia spp. such as A. velutinana; Athetis mindara, Austroasca viridigrisea, Autographa gamma, Autographa nigrisigna, Barathra brassicae, Bedellia spp., Bonagota salubricola, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp. such as C. murinana, C. podana; Cactobiastis cactorum, Cadra cauteiia, Caiingo braziliensis, Caloptilis theivora, Capua reticulana, Carposina spp. such as C. niponensis, C. sa- sakii; Cephus spp., Chaetocnema aridula, Cheimatobia brumata, C ? spp. such as C. Indicus,

C. suppressalis, C. partellus; Choreutis pariana, Choristoneura spp. such as C. conflictana, C. fumiferana, C longicellana, C murinana, C occidentalis, C rosaceana; Chrysodeixis (=Pseu- doplusia) spp. such as C. eriosoma, C. includens; Cirphis unipuncta, Clysia ambiguella,

Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Cochylis hospes, Coleophora spp., Co/las eurytheme, Conopomorpha spp., Conotrache/us spp., Cop/tarsia spp., Corcyra cepha/onica, Crambus caliginosellus, Crambus teterrellus, Crocidosema (=Epinotia) aporema, Cydalima (=Diaphania) perspectalis, Cydia (=Carpocapsa) spp. such as C. pomonella, C. lati- ferreana; Dalaca noctuides, Datana integerrima, Dasychira pinicola, Dendrolimus spp. such as

D. pini, D. spectabilis, D. sibiricus; Desmia funeralis, Diaphania spp. such as D. nitidalis, D. hyalinata; Diatraea grandiosella, Diatraea saccharalis, Diphthera festiva, Earias spp. such as E. insulana, E. vittella; Ecdytolopha aurantianu, Egira (=Xylomyges) curia/is, E/asmopa/pus lignosellus, Eldana saccharina, Endopiza viteana, Ennomos subsignaria, Eoreuma loftini, Ephestia spp. such as E. cauteiia, E. elutella, E. kuehniella; Epinotia aporema, Epiphyas postvittana, Erannis tiliaria, Erionota thrax, Etie/ia spp., Eu/ia spp., Eupoecilia ambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bou liana, Faronta albilinea, Feltia spp. such as F. subterranean; Galleria mellonella, Gracillaria spp., Grapholita spp. such as G. funebrana, G. molesta, G. inopinata; Halysidota spp., Harrisina americana, Hedylepta spp., Helicoverpa spp. such as H. armigera (=Heliothis armigera), H. zea (=Heliothis zea); Heliothis spp. such as H. assulta, H. subflexa, H. virescens; Hellula spp. such as H. undalis, H. rogatalis; Helocoverpa geiotopoeon, Hemiieuca oiiviae, Herpetogramma Iicarsisaiis, Hibernia defoliaria, Hofmannophila pseudospretella, Homoeosoma electellum, Homona magnanima, Hypena scabra, Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus, Kakivoria flavofasciata, Keiferia lyco- persicella, Lambdina fisceiiaria fisceiiaria, Lambdina fisceiiaria lugubrosa, Lamprosema indicata, Laspeyresia molesta, Leguminivora glycinivorella, Lerodea eufala, Leuci nodes orbonalis, Leu- coma salicis, Leucoptera spp. such as L. coffeella, L. scitella; Leuminivora lycinivorella, Litho- colletis biancardella, Lithophane antennata, Llattia octo (=Amyna axis), Lobesia botrana, Lopho- campa spp., Loxagrotis albicosta, Loxostege spp. such as L. sticticalis, L. cereralis; Lymantria spp. such as L. dispar, L. monacha; Lyonetia clerkella, Lyonetia prunifoliella, Ma lacosoma spp. such as M. americanum, M. californicum, M. constrictum, M. neustria; Mamestra spp. such as M. brassicae, M. configurata; Mamstra brassicae, Manduca spp. such as M. quinquemaculata, M. sexta; Marasmia spp, Marmara spp., Maruca testulalis, Megalopyge lanata, Melanchra picta, Melanitis leda, Mods spp. such as M. lapites, M. repanda; Mods latipes, Monochroa fragariae, Mythimna separata, Nemapogon cloacella, Neoleucinodes elegantalis, Nepytia spp., Nymphula spp., Oiketicus spp., Omiodes indicata, Omphisa anastomosalis, Operophtera brumata, Orgyia pseudotsugata, Oria spp., Orthaga thyrisalis, Ostrinia spp. such as O. nubilalis; Oulema oryzae, Paleacrita vernata, Panolis flammea, Parnara spp., Papaipema nebris, Papilio cresphontes, Paramyelois transitella, Paranthrene regalis, Paysandisia archon, Pectinophora spp. such as P. gossypiella; Peridroma saucia, Perileucoptera spp., such as P. coffeella; Phalera bucephala, Phryganidia californica, Phthorimaea spp. such as P. operculella; Phyllocnistis citrella, Phyllo- norycter spp. such as P. biancardella, P. crataegeiia, P. issikii, P. ringoniella; Pieris spp. such as P. brassicae, P. rapae, P. napi; Pilocrocis tripunctata, Plathypena scabra, Platynota spp. such as P. flavedana, P. idaeusalis, P. stultana; Platyptilia carduidactyla, Plebejus argus, Plodia interpunctella, Plusia spp, Plutella maculipennis, Plutella xylostella, Pontia protodica, Prays spp., Prodenia spp., Proxenus /epigone, Pseudaletia spp. such as P. sequax, P. unipuncta; Pyrausta nubilalis, Rachiplusia nu, Rich/a albicosta, Rhizobius ventralis, Rhyacionia frustrana, Sabulodes aegrotata, Schizura concinna, Schoenobius spp., Schreckensteinia festaliella, Scirpophaga spp. such as S. incertulas, S. in notata; Scotia segetum, Sesamia spp. such as S. inferens, Seudyra subflava, Sitotroga cerealella, Sparganothis pilleriana, Spilonota lechriaspis, S. ocellana, Spodoptera (=Lamphygma) spp. such as S. eridania, S. exigua, S. frugiperda, S. latisfascia, S. littoralis, S. litura, S. omithogalli; Stigmella spp., Stomopteryx subsecivella, Stry- mon bazochii, Sylepta derogata, Synanthedon spp. such as S. exitiosa, Tec/a solanivora, Tele- hin ileus, Thaumatopoea pityocampa, Thaumatot/bia (=Cryptophlebia) leucotreta, Thaumetopo- ea pityocampa, Thecla spp., Theresimima ampelophaga, Thyrinteina spp, Tildenia inconspicu- ella, Tinea spp. such as T. cloacella, T. pellionella; Tineola bisselliella, Tortrix spp. such as T. viridana; Trichophaga tapetzella, Trichoplusia spp. such as T. ni; Tuta (=Scrobipalpula) absoluta, Udea spp. such as U. rubigalis, U. rubigalis; Virachola spp., Yponomeuta padella, and Zeiraphera canadensis;

insects from the order of Coleoptera, for example Acalymma vittatum, Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agrilus spp. such as A. anxius, A. planipennis, A.

sinuatus; Agriotes spp. such as A. fuscicollis, A. lineatus, A. obscurus; Alphitobius diaperinus, Amphimallus solstitialis, Anisandrus dispar, Anisoplia austriaca, Anobium punctatum, Anomala corpulenta, Anomala rufocuprea, Anoplophora spp. such as A. glabripennis; Anthonomus spp. such as A. eugenii, A. grandis, A. pomorum; Anthrenus spp., Aphthona euphoridae, Apion spp., Apogonia spp., Athous haemorrhoidalis, Atomaria spp. such as A. linearis; Attagenus spp., Au- lacophora femora/is, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as B. lentis, B. pisorum, B. rufimanus; Byctiscus betulae, Callidiellum rufipenne, Caiiopistria floridensis, Caiiosobruchus chinensis, Cameraria ohridella, Cassida nebuiosa, Cero- toma trifurcata, Cetonia aurata, Ceuthorhynchus spp. such as C assimilis, C. napi; Chaetocne- ma tibialis, Cleonus mendicus, Conoderus spp. such as C. vespertinus; Conotrachelus nenuphar, Cosmopolites spp., Costelytra zealandica, Crioceris asparagi, Cryptolestes ferrugineus, Cryptorhynchus lapathi, Ctenicera spp. such as C. destructor; Curculio spp., Cylindrocopturus spp., Cyclocephala spp., Dactyl/spa balyi, Dectes texanus, Dermestes spp., Diabrotica spp. such as D. undecimpunctata, D. speciosa, D. longicornis, D. semipunctata, D. virgifera; Diapre- pes abbreviates, Dichocrocis spp., Dicladispa armigera, Diloboderus abderus, Diocaiandra fru- menti (Diocaiandra stigmaticoiiis), Enaphaiodes rufuius, Epilachna spp. such as E. varivestis, E. vigintioctomaculata; Epitrix spp. such as E. hirtipennis, E. similaris; Eutheola humilis, Eutino- bothrus brasiliensis, Faustinus cubae, Gibbium psylloides, Gnathocerus cornutus, Hellula un- da/is, Heteronychus arator, Hylamorpha elegans, Hylobius abietis, Hylotrupes bajulus, Hypera spp. such as H. brunneipennis, H. postica; Hypomeces squamosus, Hypothenemus spp., Ips typographus, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp. such as L. bilineata, L. melanopus; Leptinotarsa spp. such as L. decemlineata; Leptispa pygmaea, Limonius californicus, Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp., Lyctus spp. such as L. bruneus; Liogenys fuscus, Macrodactylus spp. such as M. subspi- nosus; Maladera matrida, Megaplatypus mutates, Megascelis spp., Me/anotus communis, Meligethes spp. such as M. aeneus; Melolontha spp. such as M. hippocastani, M. melolontha; Metamasius hemipterus, Microtheca spp., Migdolus spp. such as M. fryanus, Monocham us spp. such as M. alternatus; Naupactus xanthographus, Niptus hololeucus, Oberia brevis, Oemona hirta, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorrhynchus sul- catus, Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon spp. such as P. brassicae, P. cochleariae; Phoracantha recurva, Phyllobius pyri, Phyllopertha horticola, Phyllophaga spp. such as P. helleri; Phyllotreta spp. such as P. chrysocephala, P. nemorum, P. striolata, P. vittula; Phyllopertha horticola, Pop/ilia japonica, Premnotrypes spp., Psacothea hilaris, Psylliodes chrysocephala, Prostephanus truncates, Psylliodes spp., Ptinus spp., Pulga saltona, Rhizopertha dominica, Rhynchophorus spp. such as R. billineatus, R. ferrugineus, R. palmarum, R. phoenicis, R. vulneratus; Saperda Candida, Scolytus schevyrewi, Scyphophorus acupunctatus, Sitona I meatus, Si tophi/us spp. such as S. granar/a, S. oryzae, S. zeamais; Sphenophorus spp. such as S. levis; Stegobium paniceum, Sternechus spp. such as S. subsignatus; Strophomorphus ctenotus, Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp. such as T. castaneum; Trogoderma spp., Tychius spp., Xylotrech us spp. such as X. pyrrhoderus; and, Zabrus spp. such as Z. tenebrioides;

insects from the order of Diptera for example Aedes spp. such as A. aegypti, A. albopictus, A. vexans; Anastrepha ludens, Anopheles spp. such as A. albimanus, A. crucians, A. freeborni, A. gambiae, A. leucosphyrus, A. maculipennis, A. minimus, A. quadrimaculatus, A. sinensis; Bac- trocera invadens, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis ca- pitata, Chrysomyia spp. such as C. bezziana, C. hominivorax, C. macellaria; Chrysops at/an- t/cus, Chrysops discalis, Chrysops siiacea, Cochliomyia spp. such as C. hominivorax; Contarinia spp. such as C. sorghicola; Cordylobia anthropophaga, Culexspp. such as C. nigripalpus, C. pip/ens, C. quinquefasciatus, C tarsalis, C tritaeniorhynchus; Culicoides furens, Culiseta in- ornata, Culiseta melanura, Cuterebra spp., Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Dasineura oxycoccana, Delia spp. such as D. antique, D. coarctata, D. piatura, D. radicum; Dermatobia hominis, Drosophila spp. such as D. suzukii, Fannia spp. such as F. canicularis; Gastraphilus spp. such as G. intestinalis; Geomyza tipunctata, Glossina spp. such as G. fus- cipes, G. morsitans, G palpalis, G. tachinoides; Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia spp. such as H. platura; Hypoderma spp. such as H. lineata; Hyppo- bosca spp., Hydrellia philippina, Leptoconops torrens, Liriomyza spp. such as L. sativae, L. tri- folii; Lucilia spp. such as L. caprina, L. cuprina, L. sericata; Lycoria pectoralis, Mansonia titilla- nus, Mayetiola spp. such as M. destructor; Musca spp. such as M. autumnalis, M. domestical Muscina stabulans, Oestrus spp. such as O. ovis; Opomyza florum, Oscinella spp. such as O. frit; Orseolia oryzae, Pegomya hysocyami, Phlebotomus argentipes, Phorbia spp. such as P. antiqua, P. brassicae, P. coarctata; Phytomyza gymnostoma, Prosimulium mixtum, Psila rosae, Psorophora coiumbiae, Psorophora discolor, Rhagoletis spp. such as R. cerasi, R. cinguiate, R. indifferens, R. mendax, R. pomonella; Rivellia quadrifasciata, Sarcophaga spp. such as S.

haemorrhoidalis; Simulium vittatum, Sitodiplosis mosellana, Stomoxys spp. such as S. calci- trans; Tabanus spp. such as T. atratus, T. bovinus, T. lineola, T. similis; Tannia spp.,

Thecodiplosis japonensis, Tipula oleracea, Tipula paludosa, and Wohlfahrtia spp;

insects from the order of Thysanoptera for example, Baliothrips biformis, Dichromothrips corbetti, Dichromothrips ssp., Echinothrips americanus, Enneothrips flavens, Frankliniella spp. such as F. fusca, F. occidentalis, F. tritici; Heliothrips spp., Hercinothrips femora/is, Kakothrips spp., Microcephalothrips abdominalis, Neohydatothrips samayunkur, Pezothrips kellyanus, Rhipiphorothrips cruentatus, Scirtothrips spp. such as S. citri, S. dorsalis, S. perseae;

Stenchaetothrips spp, Taeniothrips cardamom,^' Taeniothrips inconsequens, Thrips spp. such as T. imagines, T. hawaiiensis, T. oryzae, T. palmi, T. parvispinus, T. tabaci;

insects from the order of Hemiptera for example, Acizzia jamatonica, Acrosternum spp. such as A. ^e/Acyrthosipon spp. such as A. onobrychis, A. pisum; Adelges laricis, Adelges tsu- gae, Adelphocoris spp., such as A. rapidus, A. superbus; Aeneolamia spp., Agonoscena spp., Aulacorthum solani, Aleurocanthus woglumi, Aleurodes spp., Aleurodicus disperses, Aleuro- lobus barodensis, Aleurothrixus spp., Amrasca spp., Anasa tristis, Antestiopsis spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphidula nasturtii, Aphis spp. such as A. craccivora, A. fabae, A. forbesi, A. gossypii, A. grossulariae, A. maidiradicis, A. pomi, A. sambuci, A.

schneideri, A. spiraeco/a; Arbor/d/a apica/is, Ar/lus cr/tatus, Aspidiella spp., Aspidiotus spp., Atanus spp., Au/acaspis yasumatsui, Aulacorthum solani, Bactericera cockerelli (Paratrioza cockerelli), Bemisia spp. such as B. argentifolii, B. tabaci (Aleurodes tabaci); Blissus spp. such as B. leucopterus; Brachycaudus spp. such as B. cardui, B. heiichrysi, B. persicae, B. prunicoia; Brachycolus spp., Brachycorynella asparagi, Brevicoryne brassicae, Cacopsylla spp. such as C. fulguralis, C. pyricola (Psylla piri); Calligypona marginata, Calocoris spp., Campylomma livida, Capitophorus horn/, Carneocephala fulgida, Cavelerius spp., Ceraplastes spp., Ceratovacuna lanigera, Ceroplastes ceriferus, Cerosipha gossypii, Chaetosiphon fragaefolii, Chionaspis tega- lensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbiia, Cimex spp. such as C hemipterus, C lectularius; Coccomytilus halli, Coccus spp. such as C. hespe- ridum, C. pseudomagnoliarum, Corythucha arcuata, Creontiades dilutus, Cryptomyzus ribis, Chrysomphalus aonidum, Cryptomyzus ribis, Ctenarytaina spatulata, Cyrtopeltis notatus,

Dalbulus spp., Dasynus piperis, Dialeurodes spp. such as D. citrifolii; Dalbulus maidis, Diapho- rina spp. such as D. citri; Diaspis spp. such as D. bromeliae; Dichelops furcatus, Diconocoris hewetti, Dora/is spp., Dreyfus/a nordmann/anae, Dreyfus/a p/ceae, Drosicha spp., Dysaphis spp. such as D. plantaginea, D. pyri, D. radicola; Dysaulacorthum pseudosolani, Dysdercus spp. such as D. cingulatus, D. intermedius; Dysmicoccus spp., Edessa spp., Geocoris spp., Empo- asca spp. such as E. fabae, E. so/ana; Epidiaspis leperii, Eriosoma spp. such as E. lanigerum, E. pyricola; Erythroneura spp., Eurygaster pp. such as E. integriceps; Euscelis bilobatus, Euschistus spp. such as E. heros, E. impictiventris, E. servus; Fiorinia theae, Geococcus coffeae, Glycaspis brimblecombei, Halyomorpha spp. such as H. halys; Heliopeltis spp.,

Homalodisca vitripennis (=H. coagulata), Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lactucae, lcerya spp. such as /. purchase; Idiocerus spp., Idioscopus spp., Laodelphax stria- tellus, Lecanium spp., Lecanoideus floccissimus, Lepidosaphes spp. such as L. ulmi; Lepto- corisa spp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp. such as L. hesperus, L.

lineolaris, L. pratensis; Maconellicoccus hirsutus, Marchalina hellenica, Macropes excavatus, Macrosiphum spp. such as M. rosae, M. avenae, M. euphorbiae; Macrosteles quadrilineatus, Mahanarva fimbriolata, Megacopta cribraria, Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari, Melanocallis (=Tinocallis) caryaefoliae, Metcafiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzocallis coryli, Murgantia spp., Myzus spp. such as M. ascalonicus, M. cerasi, M. nicotianae, M. persicae, M. varians; Nasonovia ribis-nigri, Neo- toxoptera formosana, Neomegalotomus spp, Nephotettix spp. such as N. malayanus, N. nigro- pictus, N. parvus, N. virescens; Nezara spp. such as N. viridula; Nilaparvata lugens, Nysius huttoni, Oebalus spp. such as O. pugnax; Oncometopia spp., Orthezia praelonga, Oxycaraenus hyaiinipennis, Parabemisia myricae, Parlatoria spp., Parthenolecanium spp. such as P. corni, P. persicae; Pemphigus spp. such as P. bursarius, P. popuiivenae; Peregrinus maidis, Perkinsieiia saccharic/da, Phenacoccus spp. such as P. acer/s, P. gossypii; Ph/oeomyzus passerin/i, Phoro- don humu/i, Phylloxera spp. such as P. devastatrix, Piesma quadrata, Piezodorus spp. such as P. guildinii; Pinnaspis aspidistrae, Planococcus spp. such as P. citri, P. ficus; Prosapia bicincta, Protopulvinaria pyriformis, Psallus seriatus, Pseudacysta persea, Pseudaulacaspis pentagona, Pseudococcus spp. such as P. comstocki; Psylla spp. such as P. mail; Pteroma/us spp., Pul- vinaria amygdali, Pyrilla spp., Quadraspidiotus spp., such as Q. perniciosus; Quesada gigas, Rastrococcus spp., Reduvius senilis, Rhizoecus americanus, Rhodnius spp., Rhopalomyzus ascalonicus, Rhopalosiphum spp. such as R. pseudobrassicas, R. insertum, R. maidis, R. padi; Saga todes spp., Sahlbergella singularis, Saissetia spp., Sappaphis mala, Sappaph/s mail, Scaptocoris spp., Scaphoides titanus, Schizaphis graminum, Schizoneura lanuginosa, Scotino- phora spp., Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Solu- bea insularis, Spissistilus festinus (=Stictocephala festina), Stephanitis nashi, Stephanitis pyrio- ides, Stephanitis takeyai, Tenalaphara malayensis, Tetraleurodes perseae, Therioaphis maculate, Thyanta spp. such as T. accerra, T. perditor; Tibraca spp., Tomaspis spp., Toxoptera spp. such as T. aurantii; Trialeurodes spp. such as T. abutiionea, T. ricini, T. vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. such as U. citri, U. yanonensis; and Viteus vitifolii,

Insects from the order Hymenoptera for example Acanthomyops interjectus, Athalia rosae, Atta spp. such as A. capiguara, A. cephalotes, A. cephalotes, A. laevigata, A. robusta, A.

sexdens, A. texana, Bombus spp., Brachymyrmex spp., Camponotus spp. such as C. florida- nus, C. pennsylvanicus, C. modoc; Cardiocondyla nuda, Chalibion sp, Crematogaster spp., Dasymutilla occidentalis, Diprion spp., Dolichovespula maculata, Dory my rmex spp., Dryocos- mus kuriphilus, Formica spp., Hoplocampa spp. such as H. minuta, H. testudinea; Iridomyrmex humilis, Lasius spp. such as L. niger, Linepithema humile, Liometopum spp., Leptocybe invasa, Monomorium spp. such as M. pharaonis, Monomorium, Nylandria fulva, Pachycondyla chinen- sis, Paratrechina longicornis, Paravespula spp., such as P. germanica, P. pennsylvanica, P. vulgaris; Pheidole spp. such as P. megacephala; Pogonomyrmex spp. such as P. barbatus, P. californicus, Polistes rubiginosa, Prenolepis impairs, Pseudomyrmex gracilis, Schelipron spp., Sirex cyaneus, Solenopsis spp. such as S. geminata, S.invicta, S. molesta, S. richteri, S. xyloni,

Sphecius speciosus, Sphexspp., Tapinoma spp. such as T. melanocephalum, T. sessile;

Tetramorium spp. such as T. caespitum, T. bicarinatum, Vespa spp. such as V. crabro; Vespula spp. such as V. squamosal; Wasmannia auropunctata, Xylocopa sp;

Insects from the order Orthoptera for example Acheta domesticus, Calliptamus italicus, Chortoicetes terminifera, Ceuthophilus spp., Diastrammena asynamora, Dociostaurus maroccanus, Gryllotalpa spp. such as G. africana, G. gryllotalpa; Gryllus spp., Hieroglyphus daganensis, Kraussaria anguiifera, Locusta spp. such as L. migratoria, L. pardalina; Meianopius spp. such as M. bivittatus, M. femurrubrum, M. mexicanus, M. sanguinipes, M. spretus;

Nomadacris septemfasciata, Oedaleus senegalensis, Scapteriscus spp., Schistocerca spp. such as S. amer/cana, S. gregar/a, Stemope/matus spp., Tachycines asynamorus, and

Zonozerus variegatus;

Pests from the Class Arachnida for example Acari,e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma spp. (e.g. A. americanum, A. variegatum, A. maculatum), Argas spp. such as A. persicu), Boophilus spp. such as B. annulatus, B. decoloratus, B. micro- plus, Dermacentor spp. such as D.siivarum, D. andersoni, D. variabilis, Hyalomma spp. such as H. truncatum, Ixodes spp. such as /. ricinus, I. rubicundus, I. scapularis, I. holocyclus, I. pacifi- cus, Rhipicephalus sanguineus, Ornithodorus spp. such as O. moubata, O. hermsi, O. turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes spp. such as P. ovis, Rhipicephalus spp. such as R. sanguineus, R. appendiculatus, Rhipicephalus everts/, Rhizogly- phus spp., Sarcoptes spp. such asS. Scabiei, and Family Eriophyidae including Acer/a spp. such as A. she/doni, A. anthocoptes, Acallitus spp., Aculops spp. such as A. lycopersici, A. pelekassi, Aculus spp. such as A. schlechtendali; Colomerus vitis, Epitrimerus pyri, Phyllocop- truta oleivora; Eriophytes ribis and Eriophyes spp. such as Eriophyes she/doni, Family Tar- sonemidae including Hemitarsonemus spp., Phytonemus pallidus and Polyphagotarsonemus latus, Stenotarsonemus spp. Steneotarsonemus spinki, Family Tenuipalpidae including Brevi- palpus spp. such as B. phoenicis, Family Tetranychidae including Eotetranych us spp., Eute- tranych us spp., Oligonych us spp., Petrobia latens, Tetranych us spp. such as T. cinnabarinus, T. evansi, T. kanzawai, T, pacificus, T. phaseulus, T. telarius and T. urticae; Bryobia praet/osa; Panonychus spp. such as P. u/mi, P. citri, Metatetranychus spp. and Oligonychus spp. such as O. pratensis, O. perseae, Vasates lycopersici, Raoiella indica, /¾/77/7yCarpoglyphidae including Carpoglyphus spp.; Penthaleidae spp. such as Halotydeus destructor, Family Demodicidae with species such as Demodexspp:, Family Trombicidea including Trombicula spp:, Family

Macronyssidae including Ornothonyssus spp:, Family Pyemotidae including Pyemotes tritici, Tyrophagus putrescentiae; Family Acaridae including Acarus siro; Family Araneida including Latrodectus mactans, Tegenaria agrestis, Chiracanthium sp, Lycosa sp Achaearanea tepidariorum and Loxosceles rec/usa;

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

nematodes, Aphelenchoides spp. such as A. besseyi; Sting nematodes, Belonolaimus spp. such as z5. longicaudatus; P\ne nematodes, Bursaphelenchus spp. such as z5. lignicolus, B. xylophilus; Ring nematodes, Criconema spp., Criconemella spp. such as C. xenop/axand C. ornata; and, Criconemoides spp. such as Criconemoides informis; Mesocriconema spp.; Stem and bulb nematodes, Ditylench us spp. such as £>. destructor, D. dipsaci; Aw\ nematodes, Dolichodorus spp.; Spiral nematodes, Heliocotylenchus multicinctus; Sheath and sheathoid nematodes, Hemicycliophora spp. and Hemicriconemoides spp.; Hirshmanniella spp.; Lance nematodes, Hoploaimus spp.; False rootknot nematodes, Nacobbus spp.; Needle nematodes, Longidorus spp. such as Z.. elongatus; Lesion nematodes, Pratylenchus spp. such as .

brachyurus, P. neglectus, P. penetrans, P. curvitatus, P. goodeyi; Burrowing nematodes, Radopholus spp. such as ?. similis; Rhadopholus spp.; Rhodopholus spp.; Reniform

nematodes, Rotylenchus spp. such as ?. robustus, R. reniformis; Scutellonema spp.; Stubby- root nematode, Trichodorus spp. such as 1 obtusus, T. primitivus; Paratrichodorus spp. such as . minor; Stunt nematodes, Tylenchorhynchus spp. such as 7! claytoni, T. dub/us; Citrus nematodes, Tylenchulus spp. such as 71 semipenetrans; Dagger nematodes, Xiphinema spp.; and other plant parasitic nematode species;

Insects from the order Isoptera for example Calotermes flavicollis, Coptotermes spp. such as C. formosanus, C. gestroi, C. acinaciformis; Cornitermes cumuians, Cryptotermes spp. such as C. brevis, C cavifrons; Globitermes sulfureus, Heterotermes spp. such as A/, aureus, H.

longiceps, H. tenuis; Leucotermes flavipes, Odontotermes spp., I ncisitermes spp. such as /. minor, I. Snyder, Marginitermes hubbardi, Mastotermes spp. such as M. darwiniensis

Neocapritermes spp. such as N. opacus, N. parvus; Neotermes spp., Procornitermes spp., Zootermopsis spp. such as Z. angusticollis, Z. nevadensis, Reticulitermes spp. such as R.

hesperus, R. tibialis, R. speratus, R. flavipes, R. grassei, R. lucifugus, R. santonensis, R.

virginicus; Termes natalensis,

Insects from the order Blattaria for example Blatta spp. such as B. orientalis, B. lateralis;

Blattella spp. such as B. asahinae, B. germanica; Leucophaea maderae, Panchlora nivea, Periplaneta spp. such as P. americana, P. austraiasiae, P. brunnea, P. fuiigginosa, P. japonica; Supella longipalpa, Parcoblatta pennsylvanica, Eurycotis floridana, Pycnoscelus surinamensis,

Insects from the order Siphonoptera for example Cediopsylla simples, Cera tophy/ius spp., Ctenocephalides spp. such as C felis, C cam^'s, Xenopsylla cheopis, Pulex irritans,

Trichodectes cam^'s, Tung a penetrans, and Nosopsyllus fascia tus,

Insects from the order Thysanura for example Lepisma saccharina , Ctenolepisma urbana, and Thermobia domestica,

Pests from the class Chilopoda for example Geophilus spp., Scutigera spp. such as Scutigera co/eoptrata;

Pests from the class Diplopoda for example B/an/^'u/us guttu/atus, Ju/us spp., Narceus spp., Pests from the class Symphyla for example Scutigerella immaculata,

Insects from the order Dermaptera, for example Forficula auricularia,

Insects from the order Collembola, for example Onychiurus spp., such as Onychiurus armatus, Pests from the order Isopoda for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber, Insects from the order Phthiraptera, for example Damalinia spp., Pediculus spp. such as Pediculus humanus capitis, Pediculus humanus corporis, Pediculus humanus humanus; Pthirus pubis, Haematopinus spp. such as Haematopinus eurysternus, Haematopinus suis;

Linognathus spp. such as Linognathus vituli; Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp.,

Examples of further pest species which may be controlled by compounds of fomula (I) include: from the Phylum Mollusca, class Bivalvia, for example, Dreissena spp.; class Gastropoda, for example, Arion pp., Biomphalaria pp., Bulinus spp., Deroceras spp., Ga/ba spp., Lymnaea spp., Oncomelania spp., Pomacea canaliclata, Succinea spp. /from the class of the helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis,

Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorch 'is spp., Cooper/a spp., Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp. such as Haemonchus contortus; Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opistorchis spp., Onchocerca volvulus, Ostertagia spp., Para- gonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercora lis, Stronyloides spp., Taenia saginata, Taenia solium, Trichineiia spiralis, Trichineiia nativa, Trichineiia britovi, Trichineiia nelsoni, Trichineiia pseudopsiraiis, Trichostronguius spp., Trichuris trichuria, Wuchereria bancrofti.

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

The present invention also relates to the non-therapeutic use of compounds of the present invention for treating or protecting animals against infestation and infection by parasites.

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

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

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

The compounds of the present invention can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits). Furthermore, the compounds of the present invention can be applied to any and all developmental stages. The compounds of the present invention can be applied as such or in form of compositions comprising the compounds of the present invention.

The compounds of the present invention can also be applied together with a mixing partner, which acts against pathogenic parasites, e.g. with synthetic coccidiosis compounds,

polyetherantibiotics such as Amprolium, Robenidin, Toltrazuril, Monensin, Salinomycin, Maduramicin, Lasalocid, Narasin or Semduramicin, or with other mixing partners as defined above, or in form of compositions comprising said mixtures.

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

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

compounds/compositions directly on the parasite, including the application directly on the animal or excluding the application directly on the animal, e.g. at it's locus for the latter) and indirect contact (applying the compounds/compositions to the locus of the parasite). The contact of the parasite through application to its locus is an example of a non-therapeutic use of the compounds of the present invention.

The term "locus" means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal.

As used herein, the term "parasites" includes endo- and ectoparasites. In some embodiments of the present invention, endoparasites can be preferred. In other embodiments, ectoparasites can be preferred. Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.

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

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides cam^'s, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus; cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Peri- planeta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orienta/is; fWes, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes aibopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimacu- latus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discaiis, Chrysops siiacea, Chrysops atianticus, Cochiiomyia hominivorax, Cordyiobia anthropophaga, Culicoides furens, Culex pip/ens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina pa/pa/is, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hipp elates spp., Hypoderma lineata, Leptoconops torrens, Lu cilia caprina, Lu cilia cuprina, Lu cilia sericata, Lycoria pectoral is, Man- sonia spp., Musca domes tica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrho- idalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis; lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bo vis, Menopon gallinae, Menacanthus stramineus and Soienopotes capillatus; ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornitho- dorus hermsi, Ornithodorus tur/cata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssus gallinae; Actinedida (Prostigmata) und Acaridida (Astigmata), e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demo- dex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pteroiichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., and Laminosioptes spp; Bugs (He- teropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp., and Arilus critatus; Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Soienopotes spp.; Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Wer- neckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.; Roundworms Nematoda: Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae^ Trichuris spp., Capillaria spp.; Rhabditida, e.g. Rhabditis spp., Strongyloides spp., Helicepha- lobus s/?/?./ Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunosto- mum spp. (Hookworm), Trichostrongylus spp., Haemonchus con tortus, Ostertagia spp., Cooper/a spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp., Aleurostrongylus abstrusus, and Dioctophyma renale; Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara can is, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi; Camallanida, e.g. Dracunculus medinensis (guinea worm); Spirurida, e.g. Thelazia spp., Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.; Thorny headed worms (Acantho- cephala), e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp.; Planarians (Plathelminthes): Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis busk/, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp:, Cercomero- morpha, in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp., Echino- coccus spp., Dipylidium can /hum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp..

As used herein, the term "animal" includes warm-blooded animals (including humans) and fish. Preferred are mammals, such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur- bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels. Particularly preferred are domestic animals, such as dogs or cats.

In general, "parasiticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various

compounds/compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.

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

For oral administration to warm-blooded animals, the formula I compounds may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the formula I compounds may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.

Alternatively, the formula I compounds may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The formula I compounds may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the formula I compounds may be formulated into an implant for subcutaneous administration. In addition the formula I compound may be

transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound.

The formula I compounds may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the formula I compound. In addition, the formula I compounds may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.

Suitable preparations are:

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

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

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

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

Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further auxiliaries such as acids, bases, buffer salts, preservatives, and solubilizers. Suitable auxiliaries for injection solutions are known in the art. The solutions are filtered and filled sterile. Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.

Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on. Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.

Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency results. Suitable thickeners are known in the art.

Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically. Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added. Suitable such auxiliaries are known in the art.

Emulsions can be administered orally, dermally or as injections. Emulsions are either of the water-in-oil type or of the oil-in-water type. They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances. Suitable hydrophobic phases (oils), suitable hydrophilic phases, suitable emulsifiers, and suitable further auxiliaries for emulsions are known in the art.

Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances,

preservatives, antioxidants, light stabilizers. Suitable suspending agents, and suitable other auxiliaries for suspensions including wetting agents are known in the art.

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

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

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

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

Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 per cent by weight, preferably of 1 to 50 per cent by weight. Furthermore, the preparations comprise the compounds of formula I against endoparasites in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 per cent by weight, very particularly preferably of 0.005 to 0.25 per cent by weight.

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

Generally it is favorable to apply solid formulations which release compounds of the present invention in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.

The compounds of the invention are better bio-degradable than those of the prior art and in addition retain a high level of pest control. This makes them superior in terms of environmental safety. In light of the structural similarities of the compounds of formula I, this significant difference in bio-degradability in favour of the compounds of the invention is unexpected and cannot be derived from what is known from the prior art.

Examples

A. Preparation examples

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

The products shown below were characterized by melting point determination, by NMR spectroscopy or by the masses ([m/z]) or retention time (RT; [min.]) determined by HPLC-MS or HPLC spectrometry.

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

HPLC method 1 : Phenomenex Kinetex 1.7 μηι XB-C18 100A; 50 x 2.1 mm; mobile phase: A: water + 0.1 % trifluoroacetic acid (TFA); B: acetonitrile; gradient: 5-100% B in 1.50 minutes; 100% B 0.25 min; flow: 0.8-1.OmI/min in 1.51 minutes at 60°C. MS: ESI positive, m/z 100-700. HPLC method 2: Phenomenex Kinetex 1.7 μηι XB-C18 100A; 50 x 2.1 mm; mobile phase: A: water + 0.1 % trifluoroacetic acid (TFA); B: acetonitrile; gradient: 5-100% B in 1.50 minutes;

100% B 0.25 min; flow: 0.8-1.OmI/min in 1.51 minutes at 60°C. MS: ESI positive, m/z 100-1400.

Example 1 : Preparation of Preparation of tert-butyl 2-chloro-4-[(E/Z)-3-(3-chloro-4-fluoro- phenyl)-4,4,4-trifluoro-but-2-enoyl]benzoate

To a solution of 60.0 g tert-butyl 4-acetyl-2-chloro-benzoate and 96 g 1-(3-chloro-4-fluoro- phenyl)-2,2,2-trifluoro-ethanone in 1200 mL 1 ,2-DCE was added 42 g K₂C0₃, then 31 g triethylamine was added. The mixture was stirred at 130°C under nitrogen for 13 h. Thin-layer- chromatography (TLC) (mobile phase: petrolether (PE) : ethylacetate (EtOAc) = 10:1 ) showed the reaction was completed. The mixture was filtered and concentrated in vacuo. The residue was purified by silica gel chromatograph (PE:EtOAc = 100:1 to 80:1 ) to give 93. Og of the title compound as a yellow oil.

¹H NMR: (400 MHz, CDCI₃): 1.62 (s, 9 H) 7.10 (d, J=8.53 Hz, 1 H) 7.13 - 7.17 (m, 1 H) 7.31 - 7.37 (m, 2 H) 7.70 -7.76 (m, 2 H) 7.83 (d, J=1.00 Hz, 1 H) ppm. Example 2: Preparation of tert-butyl 2-chloro-4-[3-(3-chloro-4-fluoro-phenyl)-4-nitro-3- (trifluoromethyl)pentanoyl]benzoate

To a solution of 2.0 g tert-butyl 2-chloro-4-[(E/Z)-3-(3-chloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2- enoyl]benzoate in 40 ml. CH₃CN was added 3.3 g DBU and 1.6 g CH3CH2NO2 at the same time. The mixture was stirred at 20°C for 20 min. The mixture was adjusted to pH=4~5 with the addition of HCI (aq.1 mol/L), extracted with EtOAc (2 x 30 ml.) and dried over Na2S0₄. The organic phase was concentrated under reduce pressure and the crude product was purified by column chromatography (PE:EtOAc=40:1 to PE:EtOAc=20:1 ) to give 56 g of the title compound (yield of 46 batches taken together).

1H NMR: (400 MHz, CDC ): 1.53 (d, J=7.06 Hz, 3 H) 1.60 (s, 9 H) 3.92 - 4.03 (m, 1 H) 4.06 - 4.15 (m, 1 H) 5.54 (d, J=6.62 Hz, 1 H) 7.19 (d, J=8.38 Hz, 1 H) 7.24 (s, 1 H) 7.43 (d, J=6.17 Hz, 1 H) 7.77 - 7.81 (m, 1 H) 7.82 - 7.86 (m, 1 H) 7.96 (s, 1 H) ppm.

Example 3: Preparation of tert-butyl 2-chloro-4-[3-(3-chloro-4-fluoro-phenyl)-4-oxo-3- (trifluoromethyl)pentanoyl]benzoate

To a solution of 7 g tert-butyl 2-chloro-4-[3-(3-chloro-4-fluoro-phenyl)-4-nitro-3-(trifluoro- methyl)pentanoyl]benzoate in 100 ml. DCM was added 0.45 g tetrapropylammonium

perruthenate (TPAP) and 3.4 g N-morpholine oxideat the same time at 0°C. Then the mixture was stirred at 20°C for 12 h. TLC (PE:EtOAc=5:1 ) showed the reaction was completed. The reaction mixture was concentrated in vacuo to give the crude product, which was purified by silica gel chromatograph (PE:EtOAc = 40:1 to 20:1 ) to give 28 g of the title compound (yield of 8 batches taken together) as a yellow solid.

H NMR: (400 MHz, CDCb): 1.65 (s, 9 H) 2.34 (s, 3 H) 3.69 (d, J=17.57 Hz, 1 H) 4.25 (d,

J=17.07 Hz, 1 H) 7.23 - 7.30 (m, 2 H) 7.45 - 7.49 (m, 1 H) 7.81 - 7.84 (m, 1 H) 7.86 - 7.90 (m, 1 H) 8.00 (d, J=1 .00 HZ, 1 H) ppm.

Example 4: Preparation of tert-butyl 2-chloro-4-[4-(3-chloro-4-fluoro-phenyl)-3-oxo-4- (trifluoromethyl)cyclopenten-1-yl]benzoate

To a solution of 5 g tert-butyl 2-chloro-4-[3-(3-chloro-4-fluoro-phenyl)-4-oxo-3-(trifluoro- methyl)pentanoyl]benzoate in 120 ml. n-heptane was added 2.7 g K2CO3, then the mixture was heated at 1 10°C under nitrogen for 12 h. Then the reaction solution was concentrated to give the crude product, which was purified by silica gel chromatography (PE:EtOAc = 60:1 to 40:1 ) to give 8.6 g of the title compound (5 batches) as yellow solid.

H NMR: (400 MHz, CDCI3): 1 .63 (s, 9 H) 3.53 (d, J=18.07 Hz, 1 H) 3.82 (dd, J=18.32, 1 .25 Hz, 1 H) 6.71 (s, 1 H) 7.18 (t, J=8.53 Hz, 1 H) 7.55 - 7.62 (m, 2 H) 7.70 (d, J=1.51 Hz, 1 H) 7.74 (dd, J=6.53, 2.01 Hz, 1 H) 7.83 (d, J=8.03 Hz, 1 H) ppm.

Example 5: Preparation of tert-butyl 4-[4-(3-chloro-4-fluoro-phenyl)-3-oxo-4-(trifluoro- methyl)cyclopenten-1-yl]-2-methyl-benzoate

To a solution of 3.5 g tert-butyl 2-chloro-4-[4-(3-chloro-4-fluoro-phenyl)-3-oxo-4-(trifluoro- methyl)cyclopenten-1-yl]benzoate in 60 ml. 1 ,4-dioxane was added 0.16 g Pd(OAc)2, 2.2 g CsF, 0.3 g tri-cyclohexylphosphine and 0.45 g methylboronic acid. The mixture was stirred at 120 °C in a sealed tube under nitrogen for 13 h. TLC (PE:EtOAc=10:1 ) showed the starting material was mostly consumed. After removal of the solvent, the residue was purified by column chromatography (PE:EtOAc=80:1 ~60:1 ) to give7 g of the title compound yield of 4 batches taken together) as yellow solid.

H NMR: (400 MHz, CDCI₃): 1 .64 (s, 9 H) 2.65 (s, 3 H) 3.56 (d, J=18.07 Hz, 1 H) 3.85 (dd, J=18.07, 1.51 Hz, 1 H) 6.72 (s, 1 H) 7.19 (t, J=8.53 Hz, 1 H) 7.49 - 7.57 (m, 2 H) 7.58 - 7.64 (m, 1 H) 7.76 - 7.79 (m, 1 H) 7.92 (d, J=8.03 Hz, 1 H) ppm

Example 6: Preparation of tert-butyl 4-[4-(3-chloro-4-fluoro-phenyl)-3-hydroxy-4-(tri- fluoromethyl)cyclopenten-1-yl]-2-methyl-benzoate

To a solution of 7 g tert-butyl 4-[4-(3-chloro-4-fluoro-phenyl)-3-oxo-4-(trifluoromethyl)cyclopenten- 1-yl]-2-methyl-benzoate and 8.3 g CeCI₃7H₂0 in 200 ml. THF and 150 ml. MeOH was added and 0.85 g NaBH₄ slowly at 0°C under nitrogen. The mixture was stirred at 20°C for 40 min. TLC (PE:EtOAc=10:1 ) showed the reaction was completed. The mixture was poured into 30 ml_ water, concentrated in vacuo and the residue was extracted with EtOAc (100 ml. x 2), the organic layer was dried over Na2S0₄ and concentrated to give 7 g of the crude title compound as yellow oil.

Example 7: Preparation of tert-butyl 4-[3-acetoxy-4-(3-chloro-4-fluoro-phenyl)-4-(tri- fluoromethyl)cyclopenten-1-yl]-2-methyl-benzoate

To a solution of 7 g tert-butyl 4-[4-(3-chloro-4-fluoro-phenyl)-3-hydroxy-4-(trifluoromethyl)cy- clopenten-1-yl]-2-methyl-benzoate in 150 ml. DCM was added 0.76 g acetic acid anhydryde (AC2O) and 5.5 g DMAP at the same time. The mixture was stirred at 0°C under nitrogen for 40 min. Then 50 ml. water were added and the organic layer was separated. The organic layer was dried over Na2S0₄ and concentrated in vacuo to give the crude product, which was purified by column chromatography (PE:EtOAc=80:1 ~60:1 ) to give 6.5 g of the title compound as yellow oil. H NMR: (400 MHz, CDC ): 1.61 (s, 9 H) 2.22 (s, 3 H) 2.61 (s, 3 H) 3.33 (d, J=16.76 HZ, 1 H) 3.73 (d, J=16.76 Hz, 1 H) 6.16 (s, 1 H) 6.38 (br. s., 1 H) 7.15 - 7.20 (m, 1 H) 7.32 (br. s., 1 H) 7.39 - 7.43 (m, 1 H) 7.53 (d, J=8.38 Hz, 1 H) 7.58 (d, J=4.85 Hz, 1 H) 7.85 (d, J=8.38 Hz, 1 H) ppm. Example 8: Preparation of tert-butyl 4-[4-(3-chloro-4-fluoro-phenyl)-4-(trifluoro- methyl)cyclopenten-1-yl]-2-methyl-benzoate

To a solution of 6.5 g tert-butyl 4-[3-acetoxy-4-(3-chloro-4-fluoro-phenyl)-4-(trifluoromethyl)cy- clopenten-1-yl]-2-methyl-benzoate in 100 ml. THF was added and 2.5 g Pd(PP i3)₄ and 0.96 g NaBH₄. The mixture was stirred at 20°C for 12h. TLC (PE:EtOAc=10:1 ) showed the reaction was completed. 30 ml. acetone were added and concentrated to give the crude product, which was purified by column chromatography (PE:EtOAc=80:1 ~70:1 ) to give the title compound (4.5 g, 78.9%) as an oil.

H NMR: (400 MHz, CDCb): 1.61 (s, 9 H) 2.56 - 2.63 (m, 3 H) 3.12 (d, J=18.07 Hz, 1 H) 3.29 (d, J=17.57 Hz, 1 H) 3.39 (d, J=18.07 HZ, 1 H) 3.55 (d, J=16.56 Hz, 1 H) 6.23 (br. s., 1 H) 7.15 (t, J=8.78 Hz, 1 H) 7.27 - 7.37 (m, 3 H) 7.50 (d, J=7.03 Hz, 1 H) 7.83 (d, J=8.03 Hz, 1 H) ppm.

Example 9: Preparation of 4-[4-(3-chloro-4-fluoro-phenyl)-4-(trifluoromethyl)cyclopenten-1-yl]-2- methyl-benzoic acid

A solution of 4.5 g tert-butyl 4-[4-(3-chloro-4-fluoro-phenyl)-4-(trifluoromethyl)cyclopenten-1-yl]-2- methyl-benzoate in 120 mL DCM at 0°C was added 7.8 g 2,6-lutidine and 1 1 g TMSOTf at the same time, then the mixture was stirred at 20°C for 12h. TLC (PE:EtOAc=10:1 ) showed the starting material was consumed completely. The reaction mixture was washed with 50 mL aqueous 1 N HCI and concentrated. The residue dissolved in 150 mL methyl-tert-butyl-ketone (MTBE) and washed with aqueous 1 N HCI and concentrated. The residue was purified by column chromatography (PE:EtOAc=50:1 ~DCM:MeOH=30:1 ) to give 7 g of the title compound (yield of two batches taken together) as yellow solid.

H NMR: (400 MHz, CDCI₃): 2.69 (s, 3 H) 3.15 (d, J=18.08 Hz, 1 H) 3.31 (d, J=16.32 Hz, 1 H) 3.41 (d, J=18.08 Hz, 1 H) 3.58 (d, J=16.32 Hz, 1 H) 6.30 (br. s., 1 H) 7.16 (t, J=8.60 Hz, 1 H) 7.31 - 7.39 (m, 2 H) 7.48 - 7.54 (m, 1 H) 8.07 (d, J=8.38 Hz, 1 H) ppm.

Example 10: Preparation of 4-[4-(3-chloro-4-fluoro-phenyl)-4-(trifluoromethyl)cyclopenten-1 -yl]- 2-methyl-N-(2-methylsulfanylethyl)benzamide [1-18]

To a mixture of 0.2 g 4-[4-(3-chloro-4-fluoro-phenyl)-4-(trifluoromethyl)cyclopenten-1-yl]-2- methyl-benzoic acid, 0.055 g 2-methylsulfanylethanamine 0.28 g Py-BrOP in 25 mL DCM was added 0.207 g Hiinig base at 20-25°C. The mixture was stirred for 14 h, before water was added and the layers were separated. The organic layer was dried over Na2S0₄ and evaporated in vacuo. Column chromatography on silica gel afforded 0.1 1 g of the title compound.

¹H NMR: (400 MHz, CDC ): 2.16 (s, 3H), 2.45 (s, 3H), 2.78 (m, 2H), 3.1 1 (m, 1 H), 3.25 (m, 1 H), 3.38 (m, 1 H), 3.54 (m, 1 H), 3.64 (m, 2H), 6.18 s, 1 H), 6.23 (s, 1 H), 6.59 (s, 1 H), 7.17 (m, 1 H), 7.27-7.41 (m, 2H), 7.53 (m, 2H), 7.78 (m, 1 H) ppm.

If not indicated otherwise the compounds were obtained as a mixture of isomers, HPLC-MS data are given for the major isomer.

Table IA - compounds of formula IA; R^2a = H, R^2b = F, R³ and R^5a = H

physical data (HPLC-MS)

No. R^4A R⁶ RT m/z

method [min] [MH]+

1-1 CI 1 ,1-dioxothietan-3-yl 1 .283 522.2 A

I-2 CI pyrimidin-2-ylmethyl 1 .305 510.2 A

I-3 CI (4R)-2-ethyl-3-oxo-isoxazolidin-4-yl 1 .293 531.0 A

I-4 CI 2-oxo-2-(2,2,2-trifluoroethylamino)ethyl 1 .290 557.0 A

I-5 CI 1.364 472.0 A

I-6 CI CH₂CF₃ 1.355 500.0 A

I -7 CI thietan-3-yl 1 .393 490.2 A

I-8 CI 2-pyridylmethyl 1 .1 15 509.0 A

I-9 CI 1 -ethyl-2-oxo-pyrrolidin-3-yl 1 .255 529.1 A

# denotes the bond to the remainder of the molecule

B. Biological examples

The activity of the compounds of formula I of the present invention could be demonstrated and evaluated in biological tests described in the following.

If not otherwise specified the test solutions were prepared as follows:

The active compound was dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water : aceton. The test solution was prepared at the day of use and in general at concentrations of ppm (wt/vol).

B.1 Green Peach Aphid (Myzus persicae)

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

The compounds were formulated using a solution containing 75% v/v water and 25% v/v

DMSO. Different concentrations of formulated compounds were pipetted into the aphid diet, using a custom built pipetter, at two replications.

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

In this test, the compounds 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-14,

1-15, 1-18, I-22 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls. B.2 Vetch aphid {Megoura viciae)

For evaluating control of vetch aphid {Megoura viciae) through contact or systemic means the test unit consisted of 24-well-microtiter plates containing broad bean leaf disks.

The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the leaf disks at 2.5 μΙ, using a custom built micro atomizer, at two replications.

After application, the leaf disks were air-dried and 5 - 8 adult aphids placed on the leaf disks inside the microtiter plate wells. The aphids were then allowed to suck on the treated leaf disks and incubated at about 23 ± 1 °C and about 50 ± 5 % relative humidity for 5 days. Aphid mortality and fecundity was then visually assessed.

1-15, 1-18, I-22 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.3 Tobacco budworm {Heliothis virescens)

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

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

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

B.4 Boll weevil {Anthonomus grandis)

For evaluating control of boll weevil {Anthonomus grandis) the test unit consisted of 24-well- microtiter plates containing an insect diet and 20-30 A. grandis eggs.

The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 20 μΙ, using a custom built micro atomizer, at two replications.

After application, microtiter plates were incubated at about 23 ± 1 °C and about 50 ± 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed.

B.5 Mediterranean fruitfly {Ceratitis capitata)

For evaluating control of Mediterranean fruitfly {Ceratitis capitata) the test unit consisted of microtiter plates containing an insect diet and 50-80 C. capitata eggs.

The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 5 μΙ, using a custom built micro atomizer, at two replications. After application, microtiter plates were incubated at about 28 ± 1 °C and about 80 ± 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed.

B.6 Diamond back moth (Plutella xylostella)

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

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

In this test, the compounds 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13,

1-14, 1-15, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 , I-22 at 300ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.7 Orchid thrips {dichromothrips corbetti)

Dichromothrips corbetti 'adults used for bioassay were obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the test compound is diluted in a 1 :1 mixture of acetone:water (vohvol), plus Kinetic HV at a rate of 0.01 % v/v.

Thrips potency of each compound was evaluated by using a floral-immersion technique. All petals of individual, intact orchid flowers were dipped into treatment solution and allowed to dry in Petri dishes. Treated petals were placed into individual re-sealable plastic along with about 20 adult thrips. All test arenas were held under continuous light and a temperature of about 28°C for duration of the assay. After 3 days, the numbers of live thrips were counted on each petal. The percent mortality was recorded 72 hours after treatment.

1-14, 1-15, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 , I-22 at 300 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.8 Green Soldier Stink Bug (Nezara viridula)

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

Soybean pods were placed in glass Petri dishes lined with moist filter paper and inoculated with ten late 3rd instar N. viridula. Using a hand atomizer, approximately 2 ml solution is sprayed into each Petri dish. Assay arenas were kept at about 25°C. Percent mortality was recorded after 5 days.

In this test, the compounds 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 ,

I-22 at 300 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls. B.9 Rice brown plant hopper (Nilaparvata lugens)

Rice seedlings are cleaned and washed 24 hours before spraying. The active compounds is formulated in 50:50 acetone:water (vohvol) and 0.1 % vol/vol surfactant (EL 620) was added. Potted rice seedlings are sprayed with 5 ml test solution, air dried, placed in cages and inoculated with 10 adults. Treated rice plants are kept at about 28-29°C and relative humidity of about 50-60%. Percent mortality is recorded after 72 hours.

In this test, the compounds 1-1 , I-2, I-3, I-4, I-5, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-14, 1-15, 1-16, 1-17, 1-18, I-20, 1-21 , I-22 at 300 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.10 Rice green leafhopper (Nephotettix virescens)

Rice seedlings are cleaned and washed 24 hours before spraying. The active compounds are formulated in 50:50 acetone:water (vohvol), and 0.1 % vol/vol surfactant (EL 620) is added. Potted rice seedlings are sprayed with 5 ml test solution, air dried, placed in cages and inoculated with 10 adults. Treated rice plants are kept at about 28-29°C and relative humidity of about 50-60%. Percent mortality is recorded after 72 hours.

1-14, 1-15, 1-17, 1-18, 1-19, I-20, 1-21 , I-22 at 300 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.1 1 Cowpea aphid {Aphis craccivora)

The active compound is dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water : acetone. Surfactant (Alkamuls® EL 620) is added at a rate of 0.1 % (vol/vol). The test solution is prepared at the day of use.

Potted cowpea plants are colonized with approximately 50 - 100 aphids of various stages by manually transferring a leaf tissue cut from infested plant 24 hours before application. Plants are sprayed after the pest population has been recorded. Treated plants are maintained on light carts at about 28°C. Percent mortality is assessed after 72 hours.

In this test, the compounds 1-1 , I-2, I-3, I-5, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-16, 1-17, I- 18, I-20, 1-21 , I-22 at 300 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.12 Silverleaf whitefly (Bemisia argentifolii)

The active compounds are formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes are inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they serve as stock solutions for which lower dilutions are made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) is included in the solution at a volume of 0.01 % (v/v).

Cotton plants at the cotyledon stage (one plant per pot) are sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants are dried in the sprayer fume hood and then removed from the sprayer. Each pot is placed into a plastic cup and about 10 to 12 whitefly adults (approximately 3-5 days old) are introduced. The insects are collected using an aspirator and a nontoxic Tygon® tubing connected to a barrier pipette tip. The tip, containing the collected insects, is then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. Cups are covered with a reusable screened lid. Test plants are maintained in a growth room at about 25°C and about 20-40% relative humidity for 3 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality is assessed 3 days after treatment, compared to untreated control plants.

In this test, the compounds 1-1 , I-2, I-3, I-4, I-7, I-9, 1-14, I-20 at 10 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.13 Southern armyworm (Spodoptera eridania)

Lima bean plants (variety Sieva) are grown 2 plants to a pot and selected for treatment at the 1st true leaf stage. Test solutions are sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants are dried in the sprayer fume hood and then removed from the sprayer. Each pot is placed into perforated plastic bags with a zip closure. About 10 to 1 1 armyworm larvae are placed into the bag and the bags zipped closed. Test plants are maintained in a growth room at about 25°C and about 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the bags. Mortality and reduced feeding are assessed 4 days after treatment, compared to untreated control plants.

In this test, the compounds 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, 1-10, 1-12, 1-14, 1-15, I-20 at 10 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.14 Red spider Mite ( Tetranychus kanzawai)

The active compound is dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water : acetone. Add surfactant (Alkamuls® EL 620) at the rate of 0.1 % (vol/vol).The test solution is prepared at the day of use.

Potted cowpea beans of 7-10 days of age are cleaned with tap water and sprayed with 5 ml of the test solution using air driven hand atomizer. The treated plants are allowed to air dry and afterwards inculated with 20 or more mites by clipping a cassava leaf section with known mite population. Treated plants are placed inside a holding room at about 25-27°C and about 50- 60% relative humidity.

Percent mortality is assessed 72 hours after treatment.

Claims

Claims:

1. A process for preparing cyclopentene compounds of formula I

wherein

A is a group A¹ , A² or A³; wherein

A¹ is:

wherein

# denotes the attachment point to the remainder of the molecule;

W is O, or S;

Y is H, N(R⁵)R⁶, or OR⁹;

A² is:

wherein

# denotes the attachment point to the remainder of the molecule;

A³ is a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated

heteromonocyclic ring containing 1 , 2, 3, or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted or partially or fully substituted by R¹¹, or A³ is a 8-, 9- or 10-membered saturated, partially or fully unsaturated heterobicyclic ring containing 1 , 2, 3, or 4 heteroatoms N, O, and/or S as ring members, which rings are unsubstituted or partially or fully R¹¹;

R¹ is Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4- alkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6- cycloalkyl, C₃-C₆-halocycloalkyl, or C(=0)OR¹⁵;

each R² is independently H, halogen, CN, N₃, N0₂, SCN, SF₅, d-C₆-alkyl, C₃-C₈- cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R⁸;

or R² is Si(R¹²)₃, OR⁹, S(0)_nR⁹, NR^10aR^10b;

phenyl , and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially or fully unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members,

which rings are unsubstituted or partially or fully substituted by same or different R¹¹ ; R³ H, C0₂R^3a, Ci-C₃-alkyl, Ci-C₃-haloalkyl;

R^3a is H, d-Cs-alkyl, or Ci-C₃-alkyloxy-Ci-C₃-alkyl;

each R⁴ is independently selected from the meanings mentioned for R²,

or two R⁴ bonded to adjacent carbon atoms may form a five- or six-membered saturated, partially or fully unsaturated carbocyclic ring;

each R⁵ is independently H, CN, Ci-Cio-alkyl, C₃-C8-cycloalkyl, C₂-Cio-alkenyl,

C2-Cio-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R⁸, or

S(0)_nR⁹ or C(=0)R⁸;

each R⁶ is independently selected from the meanings mentioned for R²;

or R⁵ and R⁶, together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- , 7- or 8-membered saturated, partially or fully unsaturated heterocyclic ring, which ring may contain 1 , 2, 3 or 4 heteroatoms O, S, N, C=0 and/or C=S as ring members, which heterocyclic ring may be partially or fully substituted by same or different halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy,

Ci-C6-alkylthio, Ci-C6-haloalkylthio, C₃-C8-cycloalkyl, C₃-C8-halocycloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, which groups are unsubstituted, or substituted by one or more same or different R⁸; or

phenyl which is unsubstituted or partially or fully substituted by same or different R¹¹; or R⁵ and R⁶ together form a group =C(R⁸)₂, =S(0)_m(R⁹)₂, =NR^10a, or =NOR⁹;

R^7a, R^7b are each independently H, halogen, CN, CrC₆-alkyl, C₃-C₈-cycloalkyl, C₂-C₆- alkenyl, or C2-C6-alkynyl, which groups are unsubstituted, partially or fully

halogenated and/or substituted by same or different R⁸;

or R^7a and R⁴ in position G³ may together form a -CH2CH2- chain;

each R⁸ is independently CN, N₃, N0₂, SCN, SF₅, C₃-C₈-cycloalkyl, C₃-C₈-halocyclo- alkyl, wherein the carbon chains are unsubstituted or partially or fully substituted by R ³;

Si(R¹²)₃, OR⁹, OSO2R⁹, S(0)_nR⁹, N(R ^0a)R ^0b, C(=O)N(R ^0a)R ^0b, C(=S)N(R ^0a)R ^0b, C(=0)OR⁹, CH=NOR⁹,

phenyl, which is unsubstituted or partially or fully substituted by same or different

R¹⁶, and

a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted or partially or fully substituted by R¹⁶,

or

two R⁸ present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyl group together form a group =0, =C(R ³)₂; =S; =S(0)_m(R ⁵)₂, =S(0)_mR ⁵N(R ^a)R ^b, =NR ^0a, =NOR⁹; or =NN(R ^0a)R ^0b; or

two radicals R⁸, together with the carbon atoms of the alkyl, alkenyl, alkynyl or cycloalkyl group which they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, which heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, and which ring is unsubstituted or partially or fully substituted by same or different R¹⁶; and R⁸ as a substituent on a cycloalkyi ring may additionally be Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R¹³; and

R⁸ in the groups -C(=0)R⁸ and

may additionally be H, halogen, Ci-C6-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, or C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different

R¹³;

each R⁹ is independently H, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-C8- cycloalkyl-Ci-C4-alkyl-, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-

C6-alkynyl, or C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R¹³; or

Ci-C₆-alkyl-C(=0)OR¹⁵,

C C₆-alkyl-C(=S)N(R ^a)R ^b, Ci-C₆-alkyl-C(=NR )N(R ^a)R ^b,

C(=0)N(R ^a)R ^b, C(=S)N(R ^a)R ^b, C(=0)OR¹⁵; or

R⁹ in the groups -S(0)_nR⁹ and -OS0₂R⁹ may additionally be Ci-C₆-alkoxy, or Ci-C₆-halo- alkoxy;

R^10a, R¹⁰ are independently from one another H, Ci-C₆-alkyl, Ci-C₆-haloalkyl, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2- C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R¹³;

Ci-C₆-alkyl-C(=0)OR¹⁵,

CrC₆-alkyl-C(=NR )N(R ^a)R ^b, Ci-C₆-alkoxy, d-C₆-haloalkoxy, Ci-C₆-alkylthio, Ci-C6-haloalkylthio,

S(0)_nR¹⁵, S(0)_nN(R ^a)R ^b, C(=0)R¹³, -C(=0)OR¹⁵, C(=0)N(R ^a)R ^b,

C(=S)R¹³, C(=S)SR¹⁵, C(=S)N(R ^a)R ^b, C(=NR )R¹³;

phenyl, is unsubstituted, or partially or fully substituted by same or different R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶; or

R^10a and R^10b form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially or fully unsaturated heterocyclic ring, which ring may contain one or two heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different halogen, Ci- Ce-alkyl, Ci-C₆-haloalkyl, Ci-C₆-alkoxy, Ci-C₆-haloalkoxy, Ci-C₆-alkylthio, Ci-C₆- haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-halo- alkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl which may be partially or fully substituted by R¹⁶, and a 3-, 4-, 5-, 6,- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶; or

_R ⁱo^a _{and R} ⁱo^b together form a group =C(R¹³)₂, =S(0)_m(R¹⁵)₂, =S(0)_mR¹⁵N(R^14a)R^14b, =NR¹⁴, or =NOR¹⁵;

R¹¹ is halogen, CN, N₃, N0₂, SCN, SF₅, Ci-Cio-alkyl, C₃-C₈-cycloalkyl, C₂-Cio-alkenyl,

C₂-Cio-alkynyl, which groups are unsubstituted, partially or fully halogenated, and/or substituted by same or different R⁸, or

OR⁹, NR^10aR^10b, S(0)_nR⁹, Si(R ²)₃;

3- , 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated aromatic heterocyclic ring comprising 1 , 2, 3, or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶; or

two R¹¹ present on the same ring carbon atom of an unsaturated or partially unsaturated heterocyclic ring may together form a group =0, =C(R¹³)₂, =S, =S(0)_m(R¹⁵)₂, =S(0)_mR¹⁵N(R^14a)R^14b, =NR¹⁴, =NOR¹⁵, or =NN(R^14a)R^14b;

or two R¹¹ bound on adjacent ring atoms form together with the ring atoms to which they are bound a saturated 3-, 4-, 5-, 6-, 7-, 8- or 9-membered ring, which ring may contain 1 or 2 heteroatoms O, S, N, and/or NR¹⁴, and/or 1 or 2 groups C=0, C=S,

C=NR¹⁴ as ring members, and which ring is unsubstituted, or partially or fully substituted by same or different halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C₂-C6-alkenyl, C₂-C6-haloalkenyl, C₂-C6-alkynyl, C₂-C6-haloalkynyl, phenyl which may be partially or fully substituted by same or different R¹⁶, and a 3-,

4- , 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring containing 1 , 2, or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶;

each R¹² is independently Ci-C4-alkyl, or phenyl which is unsubstituted, or partially or fully substituted by same or different Ci-C4-alkyl;

each R¹³ is independently CN, N0₂, OH, SH, SCN, SF₅, Ci-C₆-alkoxy, Ci-C₆-haloalk- oxy, SOn-Ci-C₆-alkyl, SO_n-Ci-C₆-haloalkyl, Si(R¹²)₃, or C(=0)N(R ^a)R ,

Cs-Cs-cycloalkyl which is unsubstituted, partially or fully halogenated or substituted by 1 or 2 same or different Ci-C4-alkyl, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-halo- alkoxy, and oxo;

phenyl, benzyl, phenoxy, wherein the phenyl moiety is unsubstituted or substituted by one or more same or different R¹⁶; and

3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring containing 1 , 2, or 3 heteroatoms N, O, and/or S, as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶; or

two R¹³ present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyl group may together be =0, =CH(Ci-C₄-alkyl), =C(Ci-C₄-alkyl)Ci-C₄-alkyl, =N(Ci-C₆-alkyl) or =NO(CrC₆-alkyl); and R¹³ as a substituent of a cycloalkyi ring may additionally be Ci-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated, or substituted by 1 or 2 CN, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, and oxo; and

R¹³ in groups =C(R¹³)₂, N=C(R¹³)₂, C(=0)R¹³, C(=S)R¹³, and C(=NR ⁴)R¹³ may additionally be H, halogen, Ci-C6-alkyl, C2-C6-alkenyl, or C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated, and/or substituted by 1 or 2 CN, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, and oxo;

each R¹⁴ is independently H, CN, Ci-C₆-alkoxy, Ci-C₆-haloalkoxy, SO_n-Ci-C₆-alkyl, SO_n- d-Ce-haloalkyl, Si(R¹²)₃,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated, and/or substituted by 1 or 2 CN, Ci-C4-alkoxy, Ci-C4-haloalkoxy, SO_n-Ci-C4-alkyl, C3-C6-cycloalkyl which is unsubstituted or substituted by 1 or 2 substituents halogen and CN; and oxo;

C3-C8-cycloalkyl which may be unsubstituted, partially or fully halogenated substituted by 1 or 2 CN, Ci-C₄-alkyl, Ci-C₄-alkoxy, Ci-C₄-haloalkoxy, SO_n-Ci-C₆-alkyl, C₃- C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl-, which groups are unsubstituted, or substituted by 1 or 2 substituents halogen and CN; and oxo;

phenyl, benzyl, pyridyl, phenoxy, which cyclic moieties are unsubstituted, or substi- tuted by one or more same or different halogen, CN, NO2, Ci-C6-alkyl, d-Ce-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C2-C4-al- kenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C₃-C6-cycloalkyl, C₃-C6- halocycloalkyl, and Ci-C6-alkoxycarbonyl; and a 3-, 4-, 5- or 6-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶;

R^14a and R^14b independently of each other, have one of the meanings given for R¹⁴; or R^14a and R^14b, together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, partially, or fully unsaturated heterocyclic ring, wherein the ring may contain 1 or 2 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, or Ci-C4-haloalkoxy; or

R^14a and R¹⁴ or R^14b and R¹⁴, together with the nitrogen atoms to which they are bound in the group -C(=NR¹⁴)N(R^14a)R^14b, form a 3-, 4-, 5-, 6- or 7-membered partially, or fully unsaturated heterocyclic ring, wherein the ring may additionally contain 1 or 2 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different halogen, Ci-C4-haloalkyl, C1-C4- alkoxy, or Ci-C4-haloalkoxy;

each R¹⁵ is independently H, CN, Si(R¹²)₃,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated, or substituted by 1 or 2 radicals C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, SO_n-Ci-C6-alkyl, or oxo; C3-C8-cycloalkyl which is unsubstituted, partially or fully halogenated and may be substituted by 1 or 2 radicals Ci-C4-alkyl, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-halo- alkoxy, SO_n-Ci-C6-alkyl, or oxo;

phenyl, benzyl, pyridyl, and phenoxy, which rings are unsubstituted, partially or fully halogenated, and/or substituted by 1 , 2 or 3 Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, or (Ci-C6-alkoxy)carbonyl;

each R¹⁶ is independently halogen, NO2, CN, OH, SH, Ci-C6-alkoxy, Ci-C6-haloalkoxy, SO_n-Ci-C6-alkyl, SO_n-Ci-C6-haloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkoxycarbonyl, Ci-C4-haloalkoxycarbonyl, aminocarbonyl, Ci-C4-alkylamino- carbonyl, di-(Ci-C4-alkyl)-aminocarbonyl, Si(R¹²)3;

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated, and/or substituted by 1 or 2 CN, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, or oxo;

C3-C8-cycloalkyl which is unsubstituted, partially or fully halogenated and/or substituted by 1 or 2 CN, Ci-C4-alkyl, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, or oxo;

phenyl, benzyl, pyridyl and phenoxy, which rings are unsubstituted, partially or fully halogenated, or substituted by 1 , 2 or 3 substituents Ci-C6-alkyl, Ci-C6-haloalkyl, Ci- C6-alkoxy, Ci-C6-haloalkoxy, or (Ci-C6-alkoxy)carbonyl; or

two R¹⁶ present together on the same atom of an unsaturated or partially unsaturated ring may be =0, =S, =N(C C₆-alkyl), =NO-C C₆-alkyl, =CH(Ci-C₄-alkyl), or =C(Ci-C₄- alkyl)₂; or

two R¹⁶ on two adjacent carbon atoms form together with the carbon atoms they are

bonded to a 4-, 5-, 6-, 7- or 8-membered saturated, partially or fully unsaturated ring, wherein the ring may contain 1 or 2 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, or Ci-C4-haloalkoxy;

each n is independently 0, 1 , or 2; and

wherein the variables have the meanings given for formula I, and

Z is SiQ¹3 wherein Q¹ is independently selected from Ci-C4-alkyl or phenyl, or P(=0)Q²2 wherein Q² is independently selected from Ci-C4-alkyl, Ci-C4-alkoxy, phenyl, halophenyl, phenoxy, or halophenoxy

which ketone is obtained by reaction of a compound of formula I II

wherein Z is as defined for formula II, and M is a metal selected from Li, Mg, Zn, or Cu or a combination of one or two or three or four of the aforementioned metals, and

X is a nucleophilic leaving group, such as halogen,

p is 1 or 2;

q is 1 , 2 or 3;

with an α , β unsaturated compound of formula IV

wherein the variables have the meanings given for formula I.

The process according to claim 1 for the preparation of compounds of formula I which correspond to formul

wherein

R¹ is Ci-C₄-haloalkyl or COOR¹⁵;

R^2a, R^2b are independently H, CI, or F;

R³ is H;

R^4A is halogen, CN, or Ci-C₄-alkyl;

R^5a is H or CrC₂-alkyl;

R⁶ is H, halogen, CN, N₃, N0₂, SCN, SF₅, Ci-C₆-alkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R⁸,

OR⁹, S(0)_nR⁹, NR^10aR^10b;

or R⁶ is phenyl which may be partially or fully substituted by R¹¹ ; or

3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially or fully unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹¹ ;

each R⁸ is independently CN, N₃, N0₂, SCN, SF₅, C₃-C₈-cycloalkyl, C₃-C₈-halocyclo- alkyl, wherein the carbon chains are unsubstituted, or partially or fully substituted by same or different R¹³;

OR⁹, OSO2R⁹, S(0)_nR⁹, N(R^10a)R^10b, C(=O)N(R^10a)R^10b,

C(=S)N(R ^0a)R ^0b, C(=0)OR⁹, or CH=NOR⁹; or

phenyl unsubstituted, or partially or fully substituted by same or different R¹⁶; or 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶, or two R⁸ present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyi group together form a group =0, =C(R¹³)₂; =S; =S(0)_m(R¹⁵)₂, =S(0)_mR¹⁵N(R ^4a)R ^4b, =NR^10a, =NOR⁹; or =NN(R^10a)R^10b; or

two radicals R⁸, together with the carbon atoms of the alkyl, alkenyl, alkynyl or cycloalkyi group which they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, which heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, and which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶; and

R⁸ as a substituent on a cycloalkyi ring may additionally be Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R¹³; and

R⁸ in the groups -C(=0)R⁸ and

R¹³;

R¹⁵ is H or Ci-Oalkyl; by cyclysation under basic conditions of a compound of formula I I which corresponds to formula I IA

wherein the variables are defined as for formula IA, and Z is as defined in claim 1 , which is obtained by reaction of a compound of formula II I as defined in claim 1 , with a ketone of formula IV which cor

wherein the variables are defined as for formula IA.

Compounds of formula IA as defined in claim 2.

Compounds of formula IA according to claim 3, wherein

R¹ is CF₃ or COOR¹⁵;

R^2a is H,

R²^ is F;

R³ is H;

R^4A is halogen, CN, or Ci-C₄-alkyl, preferably CI, or CH₃; R^5a is H or CH₃;

R⁶ is H , CN , N0₂, SCN , Ci-C₆-alkyl, C₃-Ce-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R⁸;

or R⁶ is OR⁹, S(0)_nR⁹, N R^10aR^10b; or

phenyl which is unsubstituted or partially or fully substituted by R^{1 1} ; or

3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially or fully unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms N , O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R^{1 1} ;

each R⁸ is independently CN , NO2, SCN , SF₅, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, wherein the carbon chains are unsubstituted, or partially or fully substituted by same or different R¹³;

OR⁹, OSO2R⁹, S(0)_nR⁹, N(R ^0a)R ^0b, C(=O)N(R ^0a)R ^0b,

C(=S)N(R ^0a)R ^0b, C(=0)OR⁹, or CH=NOR⁹; or

phenyl which is unsubstituted, or partially or fully substituted by same or different R¹⁶; or

two R⁸ present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyi group together form a group =0, =C(R ³)₂; =S; =S(0)_m(R ⁵)₂, =S(0)_mR ⁵N(R ^4a) R ^4b, =N R ^0a, =NOR⁹; or =N N(R ^0a)R ^0b; or

two radicals R⁸, together with the carbon atoms of the alkyl, alkenyl, alkynyl or cycloalkyi group which they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, which heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms N , O, and/or S as ring members, and which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶; and

R⁸ in the groups -C(=0) R⁸ and

may additionally be H , halogen, Ci-C6-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, or C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R¹³; and

R¹⁵ is H or Ci-C₂-alkyl.

The process according to claim 1 for the preparation of compounds of formula I which correspond to formula IB

wherein

R¹ is CrC₄-haloalkyl;

R³ is H;

R⁶ is H, halogen, CN, N₃, N0₂, SCN, SF₅, Ci-C₆-alkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl,

C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R⁸,

or R⁶ is OR⁹, S(0)_nR⁹, or NR^10aR^10b; or

phenyl which is unsubstituted, or partially or fully substituted by same or different R¹¹; or

3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially or fully unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹¹;

each R⁸ is independently CN, N₃, N0₂, SCN, SF₅, C₃-C₈-cycloalkyl, C₃-C₈-halo- cycloalkyl, wherein the carbon chains are unsubstituted, or partially or fully substituted by same or different R¹³;

OR⁹, OS0₂R⁹, S(0)_nR⁹, N(R ^0a)R ^0b, C(=O)N(R ^0a)R ^0b,

C(=S)N(R ^0a)R ^0b, C(=0)OR⁹, CH=NOR⁹; or

phenyl which is unsubstituted, or partially or fully substituted by same or different

R¹⁶; or

3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2, or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶, or

two R⁸ present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyi group together form a group =0, =C(R ³)₂; =S; =S(0)_m(R ⁵)₂, =S(0)_mR ⁵N(R ^4a)R ^4b, =NR ^0a, =NOR⁹; or =NN(R ^0a)R ^0b; or

R⁸ as a substituent on a cycloalkyi ring may additionally be Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl, which groups are unsubstituted, or substituted by one or more same or different R¹³; and

R⁸ in the groups -C(=0)R⁸ and may additionally be H, halogen, Ci-C6-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, or C2-C6-haloalkynyl, which groups are unsubstituted, or substituted by one or more same or different R¹³. by cyclysation under basic conditions of a compound of formula II which corresponds to formula IIB

wherein the variables are as defined for formula IB, and Z is as defined in claim 1 , which is obtained by reaction of a compound of formula III as defined in claim 1 with a ketone of formula IV which co

wherein the variables are as defined for formula IB.

Compounds of formula IB as defined in claim 5.

Compounds of formula IB according to claim 6, wherein

R¹ is CF₃;

R³ is H;

R⁶ is H, CN, NO2, SCN, SF₅, C C₆-alkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R⁸,

or R⁶ is OR⁹, S(0)_nR⁹, or NR^10aR^10b; or

R¹¹; or

OR⁹, OSO2R⁹, S(0)_nR⁹, N(R^10a)R^10b, C(=O)N(R^10a)R^10b,

C(=S)N(R^10a)R^10b, C(=0)OR⁹, CH=NOR⁹; or

phenyl which is unsubstituted, or substituted by one or more same or different R¹⁶; or

3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2, or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶, or two R⁸ present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyi group together form a group =0, =C(R¹³)₂; =S; =S(0)_m(R¹⁵)₂, =S(0)_mR¹⁵N(R ^4a)R ^4b, =NR^10a, =NOR⁹; or =NN(R^10a)R^10b; or

R⁸ in the groups -C(=0)R⁸ and

R¹³;

The process according to claim 1 for the preparation of compounds of formula I which correspond to formula IC

R¹ is Ci-C₄-haloalkyl;

R^2a, R^2b are independently H, CI, or F;

R³ is H;

R^4A is halogen, CN, or Ci-C₄-alkyl;

heteromonocyclic ring containing 1 , 2, 3, or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted or partially or fully substituted by same or different R¹¹ by cyclysation under basic conditions of a compound of formula I I which corresponds to formula I IC

wherein the variables are as defined for formula IC, and Z is as defined in claim 1 , which is obtained by reaction of a compound of formula II I as defined in claim 1 with a ketone of formula IV which corresponds to formula IVC

wherein the variables are as defined for formula IC. Compounds of formula IC as defined in claim 8.

0. Compounds of formula IC according to claim 9, wherein

R is CF₃;

R^2a is H,

R^2b is F;

R³ is H;

R^4A is CN;

heteromonocyclic ring containing 1 , 2, 3, or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted or partially or fully substituted by same or different R¹¹ ,

R¹¹ is halogen, CN, N0₂, SCN, SF₅, Ci-Cio-alkyl, C₃-C₈-cycloalkyl, C₂-Cio-alkenyl, C₂- Cio-alkynyl, which groups are unsubstituted, partially or fully halogenated.

1. The process according to claim 1 for the preparation of compounds of formula I which correspond to formul

wherein

R¹ is CrC₄-haloalkyl;

R^2a, R^2b are independently H, CI, or F;

R³ is H;

R⁹ is H, CN, d-Ce-alkyl, Ci-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-Ci-C₄-alkyl- , C₃-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, or C2-C6- haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different SO_n-Ci-C₆-alkyl, SO_n-Ci-C₆-haloalkyl, Si(R¹²)₃, C(=0)N(R ^a)R ; or Ci-C₆-alkyl-C(=0)OR¹⁵,

CrC₆-alkyl-C(=S)N(R ^a)R ^b, Ci-C₆-alkyl-C(=NR )N(R ^a)R ^b,

Si(R ²)₃, S(0)_nR¹⁵, S(0)_nN(R ^a)R ^b, N(R ^0a)R ^0b, -N=C(R ³)₂, C(=0)R¹³, C(=0)N(R ^a)R ^b, C(=S)N(R ^a)R ^b, C(=0)OR¹⁵; or

phenyl, which is unsubstituted, or partially or fully substituted by same or different R¹⁶; or 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶; by cyclysation under basic conditions of a compound of formula II which corresponds to formula IID

wherein the variables are as defined for formula ID, and Z is as defined in claim 1 , which is obtained by reaction of a compound of formula III as defined in claim 1 with a ketone of formula IV which cor

wherein the variables are as defined for formula ID.

12. Compounds of formula ID as defined in claim 13.

Compounds of formula ID according to claim 14, wherein

R¹ is CF₃;

R²^ is CI,

R²^ is F;

R³ is H;

R⁹ is H, Ci-Ce-alkyl, Ci-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-Ci-C₄-alkyl-, C₃- Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, or C2-C6- haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different SO_n-Ci-C₆-alkyl, SO_n-Ci-C₆-haloalkyl, C(=0)N(R ^4a)R ^4b; or N(R ^0a)R ^0b, C(=0)OR¹⁵; or

3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶.

The process according to claim 1 for the preparation of compounds of formula I which correspond to formula IE

wherein

R¹ is CrC₄-haloalkyl or COOR¹⁵;

R^2a, R^2b are independently H , CI, or F;

R³ is H ;

R^4A is halogen, CN , or Ci-C₄-alkyl;

R⁶ is H , halogen, CN , N₃, N0₂, SCN , SF₅, Ci-C₆-alkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R⁸,

OR⁹, S(0)_nR⁹, N R^10aR^10b;

or R⁶ is phenyl which may be partially or fully substituted by R^{1 1} ; or

R^7a is H , halogen, CN , Ci-Ce-alkyl, C₃-C8-cycloalkyl, C₂-Ce-alkenyl, or C₂-Ce-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R⁸;

each R⁸ is independently CN , N₃, N0₂, SCN , SF₅, C₃-C₈-cycloalkyl, C₃-C₈-halocyclo- alkyl, wherein the carbon chains are unsubstituted, or partially or fully substituted by same or different R¹³;

OR⁹, OSO2R⁹, S(0)_nR⁹, N(R^10a)R^10b, C(=O)N(R^10a)R^10b,

C(=S)N(R^10a)R¹⁰ , C(=0)OR⁹, or CH=NOR⁹; or

phenyl unsubstituted, or partially or fully substituted by same or different R¹⁶; or 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N , O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶, or

two R⁸ present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyl group together form a group =0, =C(R¹³)₂; =S; =S(0)_m(R¹⁵)₂, =S(0)_mR¹⁵N(R ^4a) R ⁴ , =N R^10a, =NOR⁹; or =N N(R^10a)R¹⁰ ; or

two radicals R⁸, together with the carbon atoms of the alkyl, alkenyl, alkynyl or cycloalkyl group which they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, which heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms N , O, and/or S as ring members, and which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶; and

R⁸ as a substituent on a cycloalkyl ring may additionally be Ci-C6-alkyl, Ci-C6-haloalkyl, C₂-C6-alkenyl, C₂-C6-haloalkenyl, C₂-C6-alkynyl, and C₂-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R¹³; and R⁸ in the groups -C(=0)R⁸ and =C(R⁸)₂ may additionally be H, halogen, Ci-C₆-alkyl, Ci-C₆- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, or C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different

R¹³;

R⁹ is H, CN, d-Ce-alkyl, Ci-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-Ci-C₄-alkyl- , C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, or C2-C6- haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different SO_n-Ci-C₆-alkyl, SO_n-Ci-C₆-haloalkyl, Si(R ²)₃, C(=0)N(R ^a)R ^b; or Ci-C₆-alkyl-C(=0)OR¹⁵,

Si(R¹²)₃, S(0)_nR¹⁵, S(0)_nN(R ^a)R , N(R ^0a)R ⁰ , -N=C(R¹³)₂, C(=0)R¹³, C(=0)N(R^14a)R¹⁴ , C(=S)N(R^14a)R¹⁴ , C(=0)OR¹⁵; or

3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶; and R¹⁵ is H or Ci-C₄-alkyl; by cyclysation under basic conditions of a compound of formula II which corresponds to formula HE

wherein the variables are defined as for formula IE, and Z is as defined in claim 1 , which is obtained by reaction of a compound of formula III as defined in claim 1 , with a ketone of formula IV which co

wherein the variables are defined as for formula IE.

5. Compounds of formula IE as defined in claim 14.

6. Compounds of formula IE according to claim 15, wherein

R¹ is CF₃;

R^2a is H,

R^2b is F;

R³ is H; R^4A is CI, or CH₃;

R⁶ is H, CN, N0₂, SCN, Ci-C₆-alkyl, C₃-Ce-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R⁸;

or R⁶ is OR⁹, S(0)_nR⁹, NR^10aR^10b; or

phenyl which may be partially or fully substituted by R¹¹; or

R^7a is H, CN, or Ci-C6-alkyl, which is unsubstituted, partially or fully halogenated and/or substituted by same or different R⁸;

each R⁸ is independently CN, NO2, SCN, SF₅, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, wherein the carbon chains are unsubstituted, or partially or fully substituted by same or different R¹³;

OR⁹, OSO2R⁹, S(0)_nR⁹, N(R ^0a)R ^0b, C(=O)N(R ^0a)R ^0b,

C(=S)N(R^10a)R^10b, C(=0)OR⁹, or CH=NOR⁹; or

3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶, or

two R⁸ present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyl group together form a group =0, =C(R ³)₂; =S; =S(0)_m(R ⁵)₂, =S(0)_mR ⁵N(R ^4a)R ^4b, =NR^10a, =NOR⁹; or =NN(R^10a)R¹⁰ ; or

R⁸ as a substituent on a cycloalkyl ring may additionally be Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R¹³; and

R⁸ in the groups -C(=0)R⁸ and =C(R⁸)₂ may additionally be H, halogen, Ci-C₆-alkyl, Ci-Ce- haloalkyI, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, or C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R¹³; and

R⁹ is H, Ci-C₆-alkyl, Ci-Ce-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-Ci-C₄-alkyl-, C₃- Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, or C2-C6-halo- alkynyl, which groups are unsubstituted, or partially or fully substituted by same or different SO_n-Ci-C₆-alkyl, SO_n-Ci-C₆-haloalkyl, C(=0)N(R ^4a)R ⁴ ; or

N(R ^0a)R ^0b, C(=0)OR¹⁵; or 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R¹⁶, and R¹⁵ is H or Ci-C₄-alkyl.

17. An agricultural or veterinary composition comprising at least one compound of formula I which corresponds to any of formulae IA, IB, IC, ID, or IE, resp., as defined in claims 3, 4, 6, 7, 9, 10, 12, 13, 15, and 16, resp., a stereoisomer thereof and/or at least one

agriculturally or veterinarily acceptable salt thereof, and at least one inert liquid and/or solid agriculturally or veterinarily acceptable carrier.

18. The use of a compound of formula I as defined in any of claims 3, 4, 6, 7, 9, 10, 12, 13, 15, and 16, resp., of a stereoisomer and/or of an agriculturally or veterinarily acceptable salt thereof for combating invertebrate pests.

19. The use of a compound of formula I as defined in any of claims 3, 4, 6, 7, 9, 10, 12, 13, 15, and 16, resp., of a stereoisomer and/or of a veterinarily acceptable salt thereof, for treating or protecting an animal from infestation or infection by invertebrate pests. 20. A method for protecting plant propagation material and/or the plants which grow therefrom from attack or infestation by invertebrate pests, which method comprises treating the plant propagation material with a pesticidally effective amount of at least one compound of formula I as defined in any of claims 3, 4, 6, 7, 9, 10, 12, 13, 15, and 16, resp., a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.