WO2013167633A1

WO2013167633A1 - Acrylamide compounds for combating invertebrate pests

Info

Publication number: WO2013167633A1
Application number: PCT/EP2013/059547
Authority: WO
Inventors: Pascal BINDSCHÄDLER; Wolfgang Von Deyn; Karsten KÖRBER; Florian Kaiser; Ralph Paulini; Deborah L. Culbertson; Paul Neese; Franz Josef Braun
Original assignee: Basf Se; Basf Schweiz Ag
Priority date: 2012-05-09
Filing date: 2013-05-08
Publication date: 2013-11-14
Also published as: BR112014027133A2

Abstract

The present invention relates to acrylamide compounds (I) which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes, and to a method for producing them. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

Description

Acrylamide compounds for combating invertebrate pests Description The present invention relates to acrylamide compounds which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes, and to a method for producing them. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

Invertebrate pests and in particular arthropods and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and to property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for combating invertebrate pests, in particular insects, arachnids and nematodes.

Related insecticidal acrylamide compounds are described in WO 201 1/054436.

However, this document does not describe compounds having the characteristic substituents as claimed in the present invention. Related compounds are moreover described in WO 2012/1 19984.

It is an object of the present invention to provide compounds that have a good pesticidal activity, in particular insecticidal activity, and show a broad activity spectrum against a large number of different invertebrate pests, especially against difficult to control arthropod pests and/or nematodes.

It has been found that these objectives can be achieved by acrylamide compounds of the formula I below, by their stereoisomers and by their salts, in particular their agriculturally or veterinarily acceptable salts, or tautomers.

Therefore, in a first aspect, the invention relates to acrylamide compounds of formula I

wherein B¹, B², B³, B⁴ and B⁵ are each independently selected from the group consisting of N and C-R², with the proviso that at most two of B¹, B², B³, B⁴ and B⁵ are N;

G¹, G⁴ and G⁵ are each independently selected from the group consisting of N and C-R⁴;

G² and G³ are each independently selected from the group consisting of N, C-A and C-R⁴; with the proviso that one of G² and G³ is C-A; with the proviso that at most two of G¹, G², G³, G⁴ and G⁵ are N;

A is a group A¹, A², A³, A⁴ or A⁵,

wherein

A¹ is selected from the group consisting of -C(=NR⁷)R⁸, and

-C(=NOR⁹)N(R ^0a)R ^0c;

A² is a group of following formula:

wherein

# denotes the bond to the remainder of the molecule;

W is selected from O and S; and

M is selected from for =C(R⁸)₂, =S(0)_m(R⁹)₂, =S(=NR ^0a)(R )₂, =NR ^0a and =NOR⁹ (so that -N=M forms a group -N=C(R⁸)₂, -N=S(0)_m(R⁹)₂ -N=S(=NR ^0a)(R⁹)₂, -N=NR^10a or -N=NOR⁹); is a group of following formula:

wherein

# denotes the bond to the remainder of the molecule; and

W² is selected from O and S; is a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, or is a 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic or heterobicyclic ring is substituted with -SH and/or =S, and is optionally further substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R¹¹; and is selected from the group consisting of -N(R^10a)-N(R^10b)-C(=O)R⁸ and -N(R ^0a)-N(R ^0b)-C(=S)R⁸; is selected from O and S; is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, amino, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, wherein the aliphatic and cycloaliphatic moieties in the five last-mentioned radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R⁸,

phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R¹¹, and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heteromono- or

heterobicyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R¹¹;

or

L and a radical R² bound in the position of B¹ or B⁵, together with the carbon atoms they are bound to, form a 5-, 6-, or 7-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO2, C=0 and C=S as ring members, wherein the ring may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents independently selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl; is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals selected from Ci-C6-alkoxy, and C3-C6- cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals selected from the group consisting of Ci-C6-alkyl and Ci-C6-alkoxy;

or

E and a radical R⁴ bound in the position of G¹ or G⁵, together with the carbon atoms they are bound to, form a 5-, 6-, or 7-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO2, C=0 and C=S as ring members, wherein the ring may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents independently selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl and C1-C6- alkoxy; is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C3-C8-

cycloalkyl, Ci-C6-alkoxy, C3-C8-cycloalkyl-Ci-C6-alkyl- and Ci-C6-alkoxy-Ci-C6- alkyl-, wherein the aliphatic and cycloaliphatic moieties in the five last-mentioned radicals may be partially or fully halogenated; is selected from the group consisting of Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, Ci-C4-alkylsulfonyl and Ci-C4-alkoxycarbonyl, wherein the aliphatic and cycloaliphatic moieties in the six last-mentioned radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals selected from the group consisting of hydroxy, cyano, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkylaminocarbonyl and Ci-C4-dialkylaminocarbonyl; each R² is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, -SF₅, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R⁸,

-Si(R¹²)₃, -OR⁹, -S(0)_nR⁹, -N(R ^0a)R ^0b,

phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R¹¹, and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heteromono- or heterobicyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R¹¹; R³ is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl and Ci-C6-alkylsulfonyl, wherein the aliphatic and cycloaliphatic moieties in the five last-mentioned radicals may be partially or fully halogenated and/or may be substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R⁸; each R⁴ is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, -SF₅, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R⁸,

-Si(R¹²)₃, -OR⁹, -S(0)_nR⁹, -N(R ^0a)R ⁰ ,

phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R¹¹, and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N,

0, S, NO, SO and SO2 as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R¹¹;

or

two radicals R⁴ bound on neighboring carbon atoms form together with the atoms to which they are bound a 5-, 6-, or 7-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO2, C=0 and C=S as ring members, wherein the ring may be substituted with 1 , 2, 3, 4 or 5, preferably

1 , 2 or 3, in particular 1 , substituents independently selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl and Ci-C6-alkoxy; R⁵ is selected from -S(O)_q(=NR ^0a)_pR⁹, -SO₂[N(R ^0a)R ⁰ ], -P(=0)(OR⁹)₂ and

-P(=S)(OR⁹)₂;

wherein q and p are independently selected from 0 and 1 ;

R⁶ is selected from the group consisting of hydrogen, cyano, Ci-Cio-alkyl, C3-C8- cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R⁸, -OR⁹, -N(R ^0a)R ^0b, -S(0)_nR⁹, -C(=O)N(R ^0a)N(R ^0a)R ^0b, -Si(R¹²)₃, -C(=0)R⁸, -P(=0)(OR⁹)₂, -P(=S)(OR⁹)₂, phenyl which may be substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹¹, and

a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R¹¹; or R⁵ and R⁶, together with the nitrogen atom to which they are bound, form a 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring, where the ring may further contain 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SOand SO2 as ring members, wherein the heterobicyclic ring may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, in particular 1 , substituents R¹⁷; is selected from the group consisting of hydrogen, cyano, Ci-Cio-alkyl, C3-C8- cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R⁸, -N(R ^0a)R ^0b, -S(0)_nR⁹, -C(=O)N(R ^0a)N(R ^0a)R ^0b, -Si(R¹²)₃, -C(=0)R⁸,

-P(=0)(OR⁹)₂, -P(=S)(OR⁹)₂,

phenyl which may be substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹¹, and

a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R¹¹; each R⁸ is independently selected from the group consisting of cyano, azido, nitro, -SCN, -SF₅, C3-C8-cycloalkyl, Cs-Cs-halocycloalkyl, where the cycloaliphatic moieties in the two last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R¹³;

-Si(R¹²)₃, -OR⁹, -OSO2R⁹, -S(0)_nR⁹, -N(R ^0a)R ⁰ , -C(=0)R¹³, -C(=O)N(R ^0a)R ^0b, -C(=S)N(R ^0a)R ⁰ , -C(=0)OR⁹,

phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, 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, e.g. 1 , 2 or 3, preferably 1 , substituents R¹⁶,

or

two R⁸ present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyi group together form a group =0,

=S(0)_mR¹⁵N(R ^4a)R ^4b, =NR ^0a, =NOR⁹; or =NN(R ^0a)R ^0b;

or

two radicals R⁸, together with the carbon atoms of an 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, where the heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, and where the carbocyclic or heterocyclic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R¹⁶; and

R⁸ as a substituent on a cycloalkyi ring is additionally selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl,

C2-C6-alkynyl and C2-C6-haloalkynyl, where the aliphatic moieties in these six radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R¹³; and

R⁸ in the groups -C(=NR⁷)R⁸, -C(=0)R⁸, =C(R⁸)₂, -NR ^0a(NR ^0b)C(=O)R⁸ and

-NR^10a(NR^10b)C(=S)R⁸ is additionally selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl, where the aliphatic moieties in the six last- mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R¹³; or

two radicals R⁸ in the group

together with the carbon atom they are bound to , form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially

unsaturated carbocyclic or heterocyclic ring, where the heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, and where the carbocyclic or heterocyclic ring is optionally substituted with one or more substituents R¹⁶;

R⁹ is independently selected from the group consisting of hydrogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last- mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R¹³, -Ci-C₆-alkyl-C(=0)OR¹⁵, -Ci-C₆-alkyl-C(=0)N(R ^a)R ,

-Ci-C₆-alkyl-C(=S)N(R ^4a)R ^4b, -Ci-C₆-alkyl-C(=NR ⁴)N(R ^4a)R ^4b,

-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 ^4a)R ⁴ , -C(=S)N(R ^4a)R ⁴ , -C(=0)OR¹⁵,

phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶; 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, e.g. 1 , 2 or 3, preferably 1 , substituents R¹⁶; and

R⁹ in the groups -S(0)_nR⁹ and -OSO2R⁹ is additionally selected from the group consisting of Ci-C6-alkoxy and Ci-C6-haloalkoxy;

or

two R⁹ in the group

may form together with the sulfur atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO, S0₂, C(=S) and C(=0) as ring members, where the

heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents selected from 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, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, 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 optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R¹⁶;

, R^10b, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R¹³;

-Ci-C₆-alkyl-C(=0)OR¹⁵, -Ci-C₆-alkyl-C(=0)N(R ^a)R ,

-Ci-C₆-alkyl-C(=S)N(R ^a)R , -Ci-C₆-alkyl-C(=NR )N(R ^a)R , Ci-C₆-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, -S(0)_nR¹⁵, -S(0)_nN(R ^a)R , -C(=0)R¹³, -C(=0)OR¹⁵, -C(=0)N(R ^a)R , -C(=S)R¹³, -C(=S)SR¹⁵, -C(=S)N(R ^4a) R ^4b, -C(=N R ⁴)R¹³;

phenyl, optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶; and

a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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, e.g. 1 , 2 or 3, preferably 1 , substituents 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 unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents selected from halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, optionally substituted with

1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, 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 optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R¹⁶;

or R ^0a and R¹⁰ together form a group =C(R¹³)₂, =S(0)_m(R¹⁵)₂,

=S(0)_mR¹⁵N(R ^4a)R ⁴ , =N R¹⁴ or =NOR¹⁵; is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R¹³;

-Ci-C₆-alkyl-C(=0)OR¹⁵, -Ci-C₆-alkyl-C(=0)N (R ^a)R ,

-Ci-C₆-alkyl-C(=S)N (R ^a)R , -Ci-C₆-alkyl-C(=N R )N(R ^a)R , Ci-C₆-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio,

-S(0)_nR¹⁵, -S(0)_nN(R ^a)R , -C(=0)R¹³, -C(=0)OR¹⁵, -C(=0)N(R ^a)R , -C(=S)R¹³, -C(=S)SR¹⁵, -C(=S)N(R ^4a) R ⁴ , -C(=N R ⁴)R¹³;

phenyl, optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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, e.g. 1 , 2 or 3, preferably 1 , substituents R¹⁶;

or

R^10a and R^10c form together with the nitrogen atom they are bonded to a 3-,

4- , 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents selected from halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, optionally substituted with

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 optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R¹⁶;

or R^10a and R^10c together form a group

=S(0)_mR¹⁵N(R ^4a)R ^4b, =NR¹⁴ or =NOR¹⁵;

R¹¹ is independently selected from the group consisting of halogen, cyano, azido, nitro, -SCN, -SF₅, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-C10- alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R⁸,

-OR⁹, -N(R ^0a)R ⁰ , -S(0)_nR⁹, -Si(R¹²)₃;

phenyl, optionally substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular

1 , substituents selected independently from R¹⁶; and

a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated aromatic heterocyclic ring comprising 1 , 2, 3 or 4 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, e.g. 1 , 2 or

3, preferably 1 , substituents selected independently from 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,

=S;

=S(0)_m(R¹⁵)₂; =S(0)_mR¹⁵N(R ^4a)R ^4b, =NR¹⁴, =NOR¹⁵, or =NN(R ^4a)R ^4b; 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, wherein the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from O, S, N, NR¹⁴, NO, SO and S0₂ and/or 1 or 2 groups selected from C=0, C=S and C=NR¹⁴ as ring members, and wherein the ring may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-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 substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R¹⁶;

R¹² is independently selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, Ci-C6-alkoxy-Ci-C6-alkyl-, Ci-C6-haloalkoxy-Ci-C6-alkyl-, and phenyl, optionally substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶;

R¹³ is independently selected from the group consisting of cyano, nitro, -OH, -SH, -SCN, -SF₅, d-Ce-alkoxy, Ci-C₆-haloalkoxy, Ci-C₆-alkylthio, Ci-C₆- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl,

Cs-Cs-cycloalkyl which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from Ci-C4-alkyl, C3-C4 cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo; phenyl, benzyl, pyridyl, phenoxy, where the cyclic moiety in the four last-mentioned radicals may be unsubstituted or carry 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring may be substituted by 1 , 2 or 3, in particular 1 , substituents 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(Ci-C₆-alkyl);

and

R¹³ as a substituent on a cycloalkyl ring is additionally selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the three last- mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , substituents selected from CN, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo;

and

R ³ in the groups =C(R¹³)₂, -N=C(R¹³)₂, -C(=0)R¹³, -C(=S)R¹³ and

-C(=NR¹⁴)R¹³ is additionally selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the three last- mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from CN, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo;

R¹⁴ is independently selected from the group consisting of hydrogen, cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from CN, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, C3-C4- cycloalkyl which may be substituted by 1 or 2, in particular 1 , substituents selected from halogen and cyano; and oxo;

Cs-Cs-cycloalkyI which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, C3-C4- cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moiety in the two last-mentioned radicals may be substituted by 1 or 2, in particular 1 , substituents selected from halogen and cyano; and oxo;

phenyl, benzyl, pyridyl, phenoxy, wherein the cyclic moieties in the four last- mentioned radicals may be unsubstituted and/or carry 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (Ci-C6-alkoxy)carbonyl; and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 or 2 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, e.g. 1 , 2 or 3, preferably 1 , substituents R¹⁶; 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 unsaturated or maximally

unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and 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 unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents selected from halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy;

R¹⁵ is independently selected from the group consisting of hydrogen, cyano, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl and oxo; Cs-Cs-cycloalkyI which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from Ci-C4-alkyl, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl and oxo;

phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3, in particular 1 , substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (Ci-C6-alkoxy)carbonyl; each R¹⁶ is independently selected from the group consisting of halogen, nitro,

cyano, -OH, -SH , Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl,

Ci-C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl;

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo;

Cs-Cs-cycloalkyI which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from Ci-C4-alkyl, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo;

phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3, in particular 1 , substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (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)Ci-C₄-alkyl;

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 unsaturated or maximally unsaturated ring, wherein the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, and wherein the ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents selected from halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy;

R¹⁷ is independently selected from the group consisting of halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy,

Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyI, Cs-Cs-halocycloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, wherein the aliphatic or cycloaliphatic moieties in the twelve last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R⁸, and phenyl which may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹¹, or two radicals R¹⁷ present on the same carbon atom may form together a group =0 or =S; each n is independently 0, 1 or 2; and

each m is independently 0 or 1 ; and the N-oxides, tautomers, stereoisomers and agriculturally or veterinarily acceptable salts thereof.

In a specific aspect, the invention relates to acrylamide compounds of formula I

wherein

B¹, B², B³, B⁴ and B⁵ are each independently selected from the group consisting of N and C-R², with the proviso that at most two of B¹, B², B³, B⁴ and B⁵ are N;

G⁴ and G⁵ are each independently selected from the group consisting of N and C-R⁴; and G³ are each independently selected from the group consisting of N, C-A and C-R⁴; with the proviso that one of G² and G³ is C-A; with the proviso that at most two of G¹, G², G³, G⁴ and G⁵ are N; A is a group A¹, A², A³, A⁴ or A⁵,

wherein

A¹ is selected from the group consisting of -C(=NR⁷)R⁸, and

-C(=NOR⁹)N(R ^0a)R ^0c;

A² is a group of following formula:

wherein

# denotes the bond to the remainder of the molecule;

W is selected from O and S; and

M is selected from for =C(R⁸)₂, =S(0)_m(R⁹)₂, =NR^10a and =NOR⁹ (so that -N=M forms a group -N=C(R⁸)₂, -N=S(0)_m(R⁹)₂, -N=NR^10a or

-N=NOR⁹); A³ is a group of following formula:

denotes the bond to the remainder of the molecule; and is selected from O and S; is a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, or is a 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic or heterobicyclic ring is substituted with -SH and/or =S, and is optionally further substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R¹¹; and

A⁵ is selected from the group consisting of -N(R^10a)-N(R^10b)-C(=O)R⁸ and

-N(R ^0a)-N(R ^0b)-C(=S)R⁸; is selected from O and S; is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, amino, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, wherein the aliphatic and cycloaliphatic moieties in the five last-mentioned radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R⁸,

or L and a radical R² bound in the position of B¹ or B⁵, together with the carbon atoms they are bound to, form a 5-, 6-, or 7-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO2, C=0 and C=S as ring members, wherein the ring may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents independently selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl; is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl which

may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals selected from Ci-C6-alkoxy, and C3-C6- cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals selected from the group consisting of Ci-C6-alkyl and Ci-C6-alkoxy;

or

E and a radical R⁴ bound in the position of G¹ or G⁵, together with the carbon atoms they are bound to, form a 5-, 6-, or 7-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO2, C=0 and C=S as ring members, wherein the ring may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents independently selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl and C1-C6- alkoxy; is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C3-C8- cycloalkyl, Ci-C6-alkoxy, C3-C8-cycloalkyl-Ci-C6-alkyl- and Ci-C6-alkoxy-Ci-C6- alkyl-, wherein the aliphatic and cycloaliphatic moieties in the five last-mentioned radicals may be partially or fully halogenated; is selected from the group consisting of Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, Ci-C4-alkylsulfonyl and Ci-C4-alkoxycarbonyl, wherein the aliphatic and cycloaliphatic moieties in the six last-mentioned radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals selected from the group consisting of hydroxy, cyano, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkylaminocarbonyl and Ci-C4-dialkylaminocarbonyl; each R² is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, -SF₅, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R⁸,

-Si(R¹²)₃, -OR⁹, -S(0)_nR⁹, -N(R ^0a)R ^0b,

heterobicyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R¹¹; is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl and Ci-C6-alkylsulfonyl, wherein the aliphatic and cycloaliphatic moieties in the five last-mentioned radicals may be partially or fully halogenated and/or may be substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R⁸;

R⁴ is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, -SF₅, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R⁸,

-Si(R¹²)₃, -OR⁹, -S(0)_nR⁹, -N(R ^0a)R ^0b,

or

1 , 2 or 3, in particular 1 , substituents independently selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl and Ci-C6-alkoxy; is selected from -S(O)_q(=NR ^0a)_pR⁹, -SO₂[N(R ^0a)R ⁰ ], -P(=0)(OR⁹)₂ and

-P(=S)(OR⁹)₂;

wherein q and p are independently selected from 0 and 1 ; is selected from the group consisting of hydrogen, cyano, Ci-Cio-alkyl, C3-C8- cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R⁸, -OR⁹, -N(R ^0a)R ^0b, -S(0)_nR⁹, -C(=O)N(R ^0a)N(R ^0a)R ^0b, -Si(R¹²)₃, -C(=0)R⁸, -P(=0)(OR⁹)₂, -P(=S)(OR⁹)₂,

a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R¹¹; or R⁵ and R⁶, together with the nitrogen atom to which they are bound, form a 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring, where the ring may further contain 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SOand SO2 as ring members, wherein the heterobicyclic ring may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, in particular 1 , substituents R¹⁷; is selected from the group consisting of hydrogen, cyano, Ci-Cio-alkyl, C3-C8- cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R⁸, -N(R ^0a)R ^0b, -S(0)_nR⁹, -C(=O)N(R ^0a)N(R ^0a)R ⁰ , -Si(R¹²)₃, -C(=0)R⁸,

-P(=0)(OR⁹)₂, -P(=S)(OR⁹)₂,

a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R¹¹; R⁸ is independently selected from the group consisting of cyano, azido, nitro, -SCN, -SF₅, C3-C8-cycloalkyl, Cs-Cs-halocycloalkyl, where the cycloaliphatic moieties in the two last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R¹³;

-Si(R¹²)₃, -OR⁹, -OSO2R⁹, -S(0)_nR⁹, -N(R ^0a)R ⁰ , -C(=0)R¹³, -C(=O)N(R ^0a)R ⁰ , -C(=S)N(R ^0a)R ^0b, -C(=0)OR⁹,

or

=S(0)_mR¹⁵N(R ^4a)R ^4b, =NR ^0a, =NOR⁹; or =NN(R ^0a)R ⁰ ;

or

R⁸ as a substituent on a cycloalkyi ring is additionally selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl, where the aliphatic moieties in these six radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R ³; and

R⁸ in the groups -C(=NR⁷)R⁸, -C(=0)R⁸, =C(R⁸)₂, -NR ^0a(NR ⁰ )C(=O)R⁸ and -NR^10a(NR^10b)C(=S)R⁸ is additionally selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl, where the aliphatic moieties in the six last- mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R¹³; R⁹ is independently selected from the group consisting of hydrogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last- mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R¹³,

-Ci-C₆-alkyl-C(=0)OR¹⁵, -Ci-C₆-alkyl-C(=0)N(R ^a)R ,

-Ci-C₆-alkyl-C(=S)N(R ^4a)R ^4b, -Ci-C₆-alkyl-C(=NR ⁴)N(R ^4a)R ^4b,

or

two R⁹ in the group

R^10b, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R¹³;

-Ci-C₆-alkyl-C(=0)OR¹⁵, -Ci-C₆-alkyl-C(=0)N (R ^a)R ,

or

R^10a and R^10b form together with the nitrogen atom they are bonded to a 3-,

or R ^0a and R¹⁰ together form a group =C(R¹³)₂, =S(0)_m(R¹⁵)₂,

-Ci-C₆-alkyl-C(=0)OR¹⁵, -Ci-C₆-alkyl-C(=0)N (R ^a)R , -Ci-C₆-alkyl-C(=S)N(R ^a)R , -Ci-C₆-alkyl-C(=NR )N(R ^a)R , Ci-C₆-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio,

-S(0)_nR¹⁵, -S(0)_nN(R ^a)R , -C(=0)R¹³, -C(=0)OR¹⁵, -C(=0)N(R ^a)R , -C(=S)R¹³, -C(=S)SR¹⁵, -C(=S)N(R ^4a)R ⁴ , -C(=NR ⁴)R¹³;

or

R^10a and R^10c form together with the nitrogen atom they are bonded to a 3-,

or R^10a and R^10c together form a group

=S(0)_mR¹⁵N(R ^4a)R ⁴ , =NR¹⁴ or =NOR¹⁵;

-OR⁹, -N(R ^0a)R ⁰ , -S(0)_nR⁹, -Si(R¹²)₃;

phenyl, optionally substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular 1 , substituents selected independently from R¹⁶; and

a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated aromatic heterocyclic ring comprising 1 , 2, 3 or 4 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, e.g. 1 , 2 or 3, preferably 1 , substituents selected independently from R¹⁶;

=S;

=S(0)_m(R¹⁵)₂; =S(0)_mR¹⁵N(R ^4a)R ^4b, =NR¹⁴, =NOR¹⁵, or =NN(R ^4a)R ^4b;

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, wherein the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from O, S, N, NR¹⁴, NO, SO and S0₂ and/or 1 or 2 groups selected from C=0, C=S and C=NR¹⁴ as ring members, and wherein the ring may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-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 substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R¹⁶;

R¹² is independently selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, Ci-C6-alkoxy-Ci-C6-alkyl-, Ci-C6-haloalkoxy-Ci-C6-alkyl-, and phenyl, optionally substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶; each R¹³ is independently selected from the group consisting of cyano, nitro, -OH, -SH, -SCN, -SF₅, d-Ce-alkoxy, Ci-C₆-haloalkoxy, Ci-C₆-alkylthio, Ci-C₆- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl,

Cs-Cs-cycloalkyl which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from Ci-C4-alkyl, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo; phenyl, benzyl, pyridyl, phenoxy, where the cyclic moiety in the four last-mentioned radicals may be unsubstituted or carry 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring may be substituted by 1 , 2 or 3, in particular 1 , substituents 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(Ci-C₆-alkyl);

and

R ³ in the groups =C(R¹³)₂, -N=C(R¹³)₂, -C(=0)R¹³, -C(=S)R¹³ and

phenyl, benzyl, pyridyl, phenoxy, wherein the cyclic moieties in the four last- mentioned radicals may be unsubstituted and/or carry 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (Ci-C6-alkoxy)carbonyl; and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 or 2 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, e.g. 1 , 2 or 3, preferably 1 , substituents R¹⁶;

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

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 unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents selected from halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy; each R¹⁵ is independently selected from the group consisting of hydrogen, cyano, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl and oxo; Cs-Cs-cycloalkyI which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from Ci-C4-alkyl, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl,

Ci-C4-alkylsulfonyl and oxo;

R¹⁶ is independently selected from the group consisting of halogen, nitro, cyano, -OH, -SH, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl,

or

each m is independently 0 or 1 ; and the N-oxides, tautomers, stereoisomers and agriculturally or veterinarily acceptable salts thereof. The present invention also provides an agricultural composition comprising at least one compound of the formula I as defined herein and/or an agriculturally acceptable salt thereof and at least one liquid or solid carrier.

The present invention also provides a veterinary composition comprising at least one compound of the formula I as defined herein and/or a veterinarily acceptable salt thereof and at least one liquid or solid carrier.

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

The present invention also relates to plant propagation material, in particular seed, comprising at least one compound of formula I and/or an agriculturally acceptable salt thereof as defined herein. The present invention further relates to a method for treating or protecting an animal from infestation or infection by parasites which comprises bringing the animal in contact with a parasiticidally effective amount of a compound of the formula I or a veterinarily acceptable salt thereof as defined herein. Bringing the animal in contact with the compound I, its salt or the veterinary composition of the invention means applying or administering it to the animal.

The term "steroisomers" encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers). Depending on the substitution pattern, the compounds of the formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. One center of chirality is the carbon atom carrying radicals R¹ and L. The invention provides both the pure enantiomers or diastereomers and their mixtures and the use according to the invention of the pure enantiomers or diastereomers of the compound I or its mixtures. Suitable compounds of the formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof. The term N-oxides relates to a form of compounds I in which at least one nitrogen atom is present in oxidized form (as NO).

The compounds of formula I may also be present in the form of the respective tautomers. Tautomery may for example be present in compounds I wherein A is A⁴ which carries a group =S. This is tautomeric to its respective enthiol form. By way of example, in case that A⁴ is 1 H-[1 ,2,4]-triazol-1 -yl which carries in the 5-position an SH or =S substituent, this result ae:

The compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) which may have a different macroscopic properties such as stability or show different biological properties such as activities. The present invention includes both amorphous and crystalline compounds of the formula I, mixtures of different crystalline states of the respective compound I, as well as amorphous or crystalline salts thereof.

Salts of the compounds of the formula I are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.

Suitable agriculturally acceptable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH⁴⁺) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy- Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium,

tetramethylammonium, tetraethylammonium, tetrabutylammonium,

2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium,

bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and

benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound of formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

By the term "veterinarily acceptable salts" is meant salts of those cations or anions which are known and accepted in the art for the formation of salts for veterinary use. Suitable acid addition salts, e.g. formed by compounds of formula I containing a basic nitrogen atom, e.g. an amino group, include salts with inorganic acids, for example hydrochlorids, sulphates, phosphates, and nitrates and salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.

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

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

The term "plants" comprises any types of plants including "non-cultivated plants" and in particular "cultivated plants". The term "non-cultivated plants" refers to any wild type species or related species or related genera of a cultivated plant.

The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf.

http://www.bio.org/speeches/pubs/er/agri_products.asp). Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e.g. by glycosylation or polymer additions such as prenylated, acetylated or

farnesylated moieties or PEG moieties.

Plants that have been modified by breeding, mutagenesis or genetic engineering, e.g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as

hydroxylphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibittors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or

imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate;

protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e.g. described in Pest Managem. Sci. 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1 185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e.g. Clearfield^® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e.g. imazamox, or ExpressSun^® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e.g.

tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glypho- sate and glufosinate, some of which are commercially available under the trade names RoundupReady^® (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance^® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink^® (glufosinate-tolerant, Bayer

CropScience, Germany). Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as δ-endotoxins, e.g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA,

CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e.g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e.g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins;

proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize- RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxy- steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e.g. WO 02/015701 ). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e.g., in

EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878,

WO 03/18810 und WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e.g. in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e.g., described in the publications mentioned above, and some of which are commercially available such as YieldGard^® (corn cultivars producing the CrylAb toxin), YieldGard^® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink^® (corn cultivars producing the Cry9c toxin), Herculex^® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]); NuCOTN^® 33B (cotton cultivars producing the CrylAc toxin), Bollgard^® I (cotton cultivars producing the CrylAc toxin), Bollgard^® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT^® (cotton cultivars producing a VIP-toxin); NewLeaf^® (potato cultivars producing the Cry3A toxin); Bt-Xtra^®, NatureGard^®, KnockOut^®, BiteGard^®, Protecta^®, Bt1 1 (e.g. Agrisure^® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).

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

Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants. Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e.g. oil crops that produce health- promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e.g. Nexera^® rape, DOW Agro Sciences, Canada).

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

The organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix C_n-C_m indicates in each case the possible number of carbon atoms in the group.

The term halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine. The term "alkyl" as used herein and in the alkyl moieties of 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 ("Ci-C₃-alkyl"),1 to 4 ("Ci-C₄-alkyl"), 1 to 6 ("Ci-C₆-alkyl"), 1 to 8 ("Ci-C₈-alkyl") or 1 to 10 ("Ci-Cio-alkyl") carbon atoms. Ci-C₂-Alkyl is methyl or ethyl. d-Cs-Alkyl is additionally propyl and isopropyl. Ci-C₄-Alkyl is additionally butyl, 1 -methylpropyl (sec- butyl), 2-methylpropyl (isobutyl) or 1 ,1 -dimethylethyl (tert-butyl). Ci-C6-Alkyl is additionally also, for example, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl,

2.2- dimethylpropyl, 1 -ethylpropyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,

3.3- dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl, or 1 -ethyl-2-methylpropyl. Ci-Cs-Alkyl is additionally also, for example, heptyl, octyl, 2-ethylhexyl and positional isomers thereof. Ci-Cio-Alkyl is additionally also, for example, nonyl, decyl and positional isomers thereof.

The term "haloalkyl" as used herein, which is also expressed as "alkyl which is partially or fully halogenated", refers to straight-chain or branched alkyl groups having 1 to 2 ("Ci-C₂-haloalkyl"), 1 to 3 ("Ci-C₃-haloalkyl"), 1 to 4 ("Ci-C₄-haloalkyl"), 1 to 6 ("Ci-C₆- haloalkyl"), 1 to 8 ("Ci-C₈-haloalkyl") or 1 to 10 ("Ci-Cio-haloalkyl") carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: in particular Ci-C2-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl,

difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,

chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoroethyl, 2-fluoroethyl,

2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl. Ci-C3-haloalkyl is additionally, for example, 1 -fluoropropyl, 2-fluoropropyl, 3-fluoropropyl,

1 .1 - difluoropropyl, 2,2-difluoropropyl, 1 ,2-difluoropropyl, 3,3-difluoropropyl,

3,3,3-trifluoropropyl, heptafluoropropyl, 1 ,1 ,1 -trifl uoroprop-2-yl , 3-chloropropyl and the like. Examples for Ci-C4-haloalkyl are, apart those mentioned for Ci-C3-haloalkyl, 4-chlorobutyl and the like. Examples for Ci-C6-haloalkyl are, apart those mentioned for Ci-C4-haloalkyl, 5-chloropentyl, 6-chlorohexyl and the like. "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"), 2 to 6 ("C₂-C₆-alkenyl"), 2 to 8 ("C₂-C₈-alkenyl") or 2 to 10 ("C₂-Cio-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; C₂-C6-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl, 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl, 1 -pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl-1 -butenyl, 2-methyl-1 -butenyl, 3-methyl-1 -butenyl, 1 -methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,

1 - methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 ,1 -dimethyl-2-propenyl,

1 .2- dimethyl-1 -propenyl, 1 ,2-dimethyl-2-propenyl, 1 -ethyl-1 -propenyl, 1 -ethyl-2- propenyl, 1 -hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1 -methyl-1 -pentenyl,

2- methyl-1 -pentenyl, 3-methyl-1 -pentenyl, 4-methyl-1 -pentenyl, 1 -methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1 -methyl-3-pentenyl,

2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1 -methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1 ,1 -dimethyl-2-butenyl, 1 ,1 -dimethyl-3-butenyl, 1 ,2-dimethyl-1 -butenyl, 1 ,2-dimethyl-2-butenyl, 1 ,2-dimethyl-3- butenyl, 1 ,3-dimethyl-1 -butenyl, 1 ,3-dimethyl-2-butenyl, 1 ,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1 -butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3- butenyl, 3,3-dimethyl-1 -butenyl, 3,3-dimethyl-2-butenyl, 1 -ethyl-1 -butenyl, 1 -ethyl-2- butenyl, 1 -ethyl-3-butenyl, 2-ethyl-1 -butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1 ,1 ,2-trimethyl-2-propenyl, 1 -ethyl-1 -methyl-2-propenyl, 1 -ethyl-2-methyl-1 -propenyl, 1 -ethyl-2-methyl-2-propenyl and the like, or C2-Cio-alkenyl, such as the radicals mentioned for C2-C6-alkenyl and additionally 1 -heptenyl, 2-heptenyl, 3-heptenyl, 1 -octenyl, 2-octenyl, 3-octenyl, 4-octenyl, 1 -nonenyl, 2-nonenyl, 3-nonenyl, 4-nonenyl,

1 - decenyl, 2-decenyl, 3-decenyl, 4-decenyl, 5-decenyl and the positional isomers thereof.

The term "haloalkenyl" as used herein, which is also expressed as "alkenyl which is partially or fully halogenated", refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 ("C₂-C₄-haloalkenyl"), 2 to 6 ("C₂-C₆-haloalkenyl"), 2 to 8 ("C₂-C₆-haloalkenyl") or 2 to 10 ("C₂-Cio-haloalkenyl") carbon atoms and a double bond in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like.

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"), 2 to 6 ("C₂-C₆-alkynyl"), 2 to 8 ("C2-C8-alkynyl"), or 2 to 10 ("C2-Cio-alkynyl") carbon atoms and one or two triple bonds in any position, for example C2-C3-alkynyl, such as ethynyl, 1 -propynyl or

2- propynyl; C2-C₄-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl,

3- butynyl, 1 -methyl-2-propynyl and the like, C2-C6-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl, 1 -pentynyl, 2-pentynyl,

3-pentynyl, 4-pentynyl, 1 -methyl-2-butynyl, 1 -methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1 -butynyl, 1 ,1 -dimethyl-2-propynyl, 1 -ethyl-2-propynyl, 1 -hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl-2-pentynyl, 1 -methyl-3-pentynyl, 1 -methyl-4- pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1 -pentynyl, 3-methyl-4- pentynyl, 4-methyl-1 -pentynyl, 4-methyl-2-pentynyl, 1 ,1 -dimethyl-2-butynyl,

1 ,1 -dimethyl-3-butynyl, 1 ,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1 - butynyl, 1 -ethyl-2-butynyl, 1 -ethyl-3-butynyl, 2-ethyl-3-butynyl, 1 -ethyl-1 -methyl-2- propynyl and the like; The term "haloalkynyl" as used herein, which is also expressed as "alkynyl which is partially or fully halogenated", refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 ("C₂-C₄-haloalkynyl"), 3 to 4 ("C₃-C₄-haloalkynyl"), 2 to 6 ("C₂-C₆-haloalkynyl"), 2 to 8 ("C₂-C₈-haloalkynyl") or 2 to 10 ("C₂-Cio-haloalkynyl") carbon atoms and one or two triple bonds in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine;

The term "cycloalkyi" 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 carbon atoms ("C3-C6-cycloalkyl") or 3 to 5 carbon atoms ("Cs-Cs-cycloalkyl") or 3 or 4 carbon atoms ("C3-C4-cycloalkyl"). Preferably, C3-C4-cycloalkyl, Cs-Cs-cycloalkyl and C3-C6- cycloalkyl are monocyclic. Examples for C3-C4-cycloalkyl are cyclopropyl and cyclobutyl. Examples of monocyclic radicals having 3 to 5 carbon atoms comprise cyclopropyl, cyclobutyl and cyclopentyl. Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of monocyclic radicals having 3 to 8 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.2.1 ]heptyl, bicyclo[3.1 .1 ]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl. Preferably, the term cycloalkyi denotes a monocyclic saturated hydrocarbon radical.

The term "halocycloalkyl" as used herein, which is also expressed as "cycloalkyi which is partially or fully halogenated", refers to mono- or bi- or polycyclic saturated hydrocarbon groups having 3 to 8 ("Cs-Cs-halocycloalkyl" ) or preferably 3 to 6 ("C3-C6- halocycloalkyl") or 3 to 5 ("Cs-Cs-halocycloalkyl") carbon ring members (as mentioned above) in which some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine. The term "cycloalkyl-Ci-C4-alkyl" refers to a Cs-Cs-cycloalkyl group ("Cs-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-Ci-C4-alkyl") as defined above (preferably a monocyclic cycloalkyi group) which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above. Examples for C3-C4-cycloalkyl-Ci- C4-alkyl are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl and cyclobutylpropyl, Examples for C3-C6-cycloalkyl-Ci-C4-alkyl, apart those mentioned for C3-C4-cycloalkyl-Ci-C4-alkyl, are cyclopentylmethyl,

cyclopentylethyl, cyclopentyl propyl, cyclohexylmethyl, cyclohexylethyl and

cyclohexylpropyl. Examples for C3-C8-cycloalkyl-Ci-C4-alkyl, apart those mentioned for C3-C6-cycloalkyl-Ci-C4-alkyl, are cycloheptylmethyl, cycloheptylethyl, cyclooctylmethyl and the like. The term "C3-C8-cycloalkyl-Ci-C6-alkyl" refers to a Cs-Cs-cycloalkyl group as defined above (preferably a monocyclic cycloalkyi group) which is bound to the remainder of the molecule via a Ci-C6-alkyl group, as defined above. Examples for C3-Cs-cycloalkyl-Ci-C6-alkyl, apart those mentioned for C3-Cs-cycloalkyl-Ci-C4-alkyl, are cyclopropylpentyl, cyclopropylhexyl, cyclobutylpentyl, cyclobutylhexyl,

cyclopentylpenty, cyclopentylhexyl and the like.

The term "C3-C8-halocycloalkyl-Ci-C4-alkyl" refers to a Cs-Cs-halocycloalkyl group as defined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.

The term "Ci-C2-alkoxy" is a Ci-C2-alkyl group, as defined above, attached via an oxygen atom. The term "Ci-C3-alkoxy" is a Ci-C3-alkyl group, as defined above, attached via an oxygen atom. The term "Ci-C4-alkoxy" is a Ci-C4-alkyl group, as defined above, attached via an oxygen atom. The term "Ci-C6-alkoxy" is a Ci-C6-alkyl group, as defined above, attached via an oxygen atom. The term "Ci-Cio-alkoxy" is a Ci-Cio-alkyl group, as defined above, attached via an oxygen atom. Ci-C2-Alkoxy is methoxy or ethoxy. Ci-C3-Alkoxy is additionally, for example, n-propoxy and

1 -methylethoxy (isopropoxy). Ci-C4-Alkoxy is additionally, for example, butoxy,

1 - methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1 -dimethylethoxy (tert- butoxy). Ci-C6-Alkoxy is additionally, for example, pentoxy, 1 -methylbutoxy,

2- methylbutoxy, 3-methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy,

2.2- dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2-dimethylbutoxy,

1 .3- dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,

1 - ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2-trimethylpropoxy, 1 -ethyl-1 - methylpropoxy or 1 -ethyl-2-methylpropoxy. Ci-Cs-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof. Ci-Cio-Alkoxy is additionally, for example, nonyloxy, decyloxy and positional isomers thereof.

The term "Ci-C2-haloalkoxy" is a Ci-C2-haloalkyl group, as defined above, attached via an oxygen atom. The term "Ci-C3-haloalkoxy" is a Ci-C3-haloalkyl group, as defined above, attached via an oxygen atom. The term "Ci-C4-haloalkoxy" is a Ci-C4-haloalkyl group, as defined above, attached via an oxygen atom. The term "Ci-C6-haloalkoxy" is a Ci-C6-haloalkyl group, as defined above, attached via an oxygen atom. The term "Ci-Cio-haloalkoxy" is a Ci-Cio-haloalkyl group, as defined above, attached via an oxygen atom. Ci-C2-Haloalkoxy is, for example, OCH2F, OCH F2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,

2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-

2- fluoroethoxy, 2,2,2-trichloroethoxy or OC2F5. Ci-C3-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3- bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5,

OCF2-C2F5, 1 -(CH₂F)-2-fluoroethoxy, 1 -(CH₂CI)-2-chloroethoxy or 1 -(CH₂Br)-2- bromoethoxy. Ci-C4-Haloalkoxy is additionally, for example, 4-fluorobutoxy,

4- chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. Ci-C6-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.

The term "Ci-C4-alkoxy-Ci-C4-alkyl" as used herein, refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above. The term

"Ci-C6-alkoxy-Ci-C6-alkyl" as used herein, refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms, as defined above, where 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, 1 -methoxyethyl, 1 -ethoxyethyl, 1 -propoxyethyl,

1 - isopropoxyethyl, 1 -n-butoxyethyl, 1 -sec-butoxyethyl, 1 -isobutoxyethyl, 1 -tert- butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n- butoxyethyl, 2-sec-butoxyethyl, 2-isobutoxyethyl, 2-tert-butoxyethyl, 1 -methoxypropyl, 1 -ethoxypropyl, 1 -propoxypropyl, 1 -isopropoxypropyl, 1 -n-butoxypropyl, 1 -sec- butoxypropyl, 1 -isobutoxypropyl, 1 -tert-butoxypropyl, 2-methoxypropyl, 2-ethoxypropyl,

2- propoxypropyl, 2-isopropoxypropyl, 2-n-butoxypropyl, 2-sec-butoxypropyl,

2- isobutoxypropyl, 2-tert-butoxypropyl, 3-methoxypropyl, 3-ethoxypropyl,

3- propoxypropyl, 3-isopropoxypropyl, 3-n-butoxypropyl, 3-sec-butoxypropyl,

3-isobutoxypropyl, 3-tert-butoxypropyl and the like.

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.

Ci-C6-Haloalkoxy-Ci-C6-alkyl is a straight-chain or branched alkyl group having from 1 to 6, especially 1 to 4 carbon atoms (=Ci-C6-haloalkoxy-Ci-C4-alkyl), wherein one of the hydrogen atoms is replaced by a Ci-C6-alkoxy group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remaining hydrogen atoms (either in the alkoxy moiety or in the alkyl moiety or in both) are replaced by halogen atoms. Ci-C4-Haloalkoxy-Ci-C4-alkyl is a straight-chain or branched alkyl group having from 1 to 4 carbon atoms, wherein one of the hydrogen atoms is replaced by a Ci-C4-alkoxy group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remaining hydrogen atoms (either in the alkoxy moiety or in the alkyl moiety or in both) are replaced by halogen atoms. Examples are

difluoromethoxymethyl (CH F2OCH2), trifluoromethoxymethyl, 1 -difluoromethoxyethyl ,

1 - trifluoromethoxyethyl, 2-difluoromethoxyethyl, 2-trifluoromethoxyethyl,

difluoromethoxy-methyl (CH3OCF2), 1 ,1 -difluoro-2-methoxyethyl, 2,2-difluoro-2- methoxyethyl and the like.

The term "Ci-C2-alkylthio" is a Ci-C2-alkyl group, as defined above, attached via a sulfur atom. The term "Ci-C3-alkylthio" is a Ci-C3-alkyl group, as defined above, attached via a sulfur atom. The term "Ci-C4-alkylthio" is a Ci-C4-alkyl group, as defined above, attached via a sulfur atom. The term "Ci-C6-alkylthio" is a Ci-C6-alkyl group, as defined above, attached via a sulfur atom. The term "Ci-Cio-alkylthio" is a Ci-Cio-alkyl group, as defined above, attached via a sulfur atom. Ci-C2-Alkylthio is methylthio or ethylthio. Ci-C3-Alkylthio is additionally, for example, n-propylthio or 1 -methylethylthio (isopropylthio). Ci-C4-Alkylthio is additionally, for example, butylthio, 1 -methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1 -dimethylethylthio (tert-butylthio). Ci-C6-Alkylthio is additionally, for example, pentylthio, 1 -methylbutylthio,

2- methylbutylthio, 3-methylbutylthio, 1 ,1 -dimethylpropylthio, 1 ,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 1 -methylpentylthio,

2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1 ,1 -dimethylbutylthio,

1 .2- dimethylbutylthio, 1 ,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio,

3.3- dimethylbutylthio, 1 -ethylbutylthio, 2-ethylbutylthio, 1 ,1 ,2-trimethylpropylthio,

1 ,2,2-trimethylpropylthio, 1 -ethyl-1 -methylpropylthio or 1 -ethyl-2-methylpropylthio.

Ci-Ce-Alkylthio is additionally, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof. Ci-Cio-Alkylthio is additionally, for example, nonylthio, decylthio and positional isomers thereof.

The term "Ci-C2-haloalkylthio" is a Ci-C2-haloalkyl group, as defined above, attached via a sulfur atom. The term "Ci-C3-haloalkylthio" is a Ci-C3-haloalkyl group, as defined above, attached via a sulfur atom. The term "Ci-C4-haloalkylthio" is a Ci-C4-haloalkyl group, as defined above, attached via a sulfur atom. The term "Ci-C6-haloalkylthio" is a Ci-C6-haloalkyl group, as defined above, attached via a sulfur atom. The term "C1-C10- haloalkylthio" is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfur atom. Ci-C₂-Haloalkylthio is, for example, SCH₂F, SCHF₂, SCF₃, SCH₂CI, SCHC , SCCI₃, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio,

2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio,

2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2- difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio or SC2F5. C1-C3- Haloalkylthio is additionally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2.2- difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio,

2.3- dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, SCH₂-C₂F₅, SCF₂-C₂F₅, 1-(CH₂F)-2-fluoroethylthio, 1 -(CH₂CI)- 2-chloroethylthio or 1 -(CH₂Br)-2-bromoethylthio. Ci-C4-Haloalkylthio is additionally, for example, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio. Ci-C6-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio,

5- brompentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio,

6- chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio. The term "Ci-C₂-alkylsulfinyl" is a Ci-C₂-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-C4-alkylsulfinyl" is a Ci-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-C6-alkylsulfinyl" is a C1-C6- alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "C1-C10- alkylsulfinyl" is a Ci-Cio-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. Ci-C₂-Alkylsulfinyl is methylsulfinyl or ethylsulfinyl. Ci-C4-Alkylsulfinyl is additionally, for example, n-propylsulfinyl, 1 -methylethylsulfinyl (isopropylsulfinyl), butylsulfinyl, 1 -methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl

(isobutylsulfinyl) or 1 ,1 -dimethylethylsulfinyl (tert-butylsulfinyl). Ci-C6-Alkylsulfinyl is additionally, for example, pentylsulfinyl, 1 -methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1 ,1 -dimethylpropylsulfinyl, 1 ,2-dimethylpropylsulfinyl,

2,2-dimethylpropylsulfinyl, 1 -ethylpropylsulfinyl, hexylsulfinyl, 1 -methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl,

1 .1 - dimethylbutylsulfinyl, 1 ,2-dimethylbutylsulfinyl, 1 ,3-dimethylbutylsulfinyl,

2.2- dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl,

1 -ethylbutylsulf inyl , 2-ethylbutylsulfinyl, 1 ,1 ,2-trimethylpropylsulfinyl,

1 ,2,2-trimethylpropylsulfinyl, 1 -ethyl-1 -methylpropylsulfinyl or 1 -ethyl-2- methylpropylsulfinyl. d-Cs-Alkylsulfinyl is additionally, for example, heptylsulfinyl, octylsulfinyl, 2-ethylhexylsulfinyl and positional isomers thereof. Ci-Cio-Alkylsulfinyl is additionally, for example, nonylsulfinyl, decylsulfinyl and positional isomers thereof.

The term "Ci-C₂-haloalkylsulfinyl" is a Ci-C₂-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-C4-haloalkylsulfinyl" is a C1-C4- haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-C6-haloalkylsulfinyl" is a Ci-C6-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-Cio-haloalkylsulfinyl" is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. Ci-C₂-Haloalkylsulfinyl is, for example, S(0)CH₂F, S(0)CHF₂, S(0)CF₃, S(0)CH₂CI, S(0)CHCI₂, S(0)CCI₃, chlorofluoromethylsulfinyl, dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2.2- difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl,

2.2.2- trichloroethylsulfinyl or S(0)C2F₅. Ci-C4-Haloalkylsulfinyl is additionally, for example, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl,

2.3- dichloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl,

3.3.3- trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl, S(0)CH₂-C₂F₅, S(0)CF₂-C₂F₅, 1 -(CH₂F)-2-fluoroethylsulfinyl, 1 -(CH₂CI)-2-chloroethylsulfinyl, 1 -(CH₂Br)-2- bromoethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorobutylsulfinyl. Ci-C6-Haloalkylsulfinyl is additionally, for example,

5- fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-brompentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl,

6- bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl. The term "Ci-C₂-alkylsulfonyl" is a Ci-C₂-alkyl group, as defined above, attached via a sulfonyl [S(0)₂] group. The term "Ci-C3-alkylsulfonyl" is a Ci-C3-alkyl group, as defined above, attached via a sulfonyl [S(0)₂] group. The term "Ci-C4-alkylsulfonyl" is a C1-C4- alkyl group, as defined above, attached via a sulfonyl [S(0)₂] group. The term "C1-C6- alkylsulfonyl" is a Ci-C6-alkyl group, as defined above, attached via a sulfonyl [S(0)₂] group. The term "Ci-Cio-alkylsulfonyl" is a Ci-Cio-alkyl group, as defined above, attached via a sulfonyl [S(0)₂] group. Ci-C₂-Alkylsulfonyl is methylsulfonyl or ethylsulfonyl. Ci-C3-Alkylsulfonyl is additionally, for example, n-propylsulfonyl or

1 - methylethylsulfonyl (isopropylsulfonyl). Ci-C4-Alkylsulfonyl is additionally, for example, butylsulfonyl, 1 -methylpropylsulfonyl (sec-butylsulfonyl),

2-methylpropylsulfonyl (isobutylsulfonyl) or 1 ,1 -dimethylethylsulfonyl (tert-butylsulfonyl). Ci-C6-Alkylsulfonyl is additionally, for example, pentylsulfonyl, 1 -methylbutylsulfonyl,

2- methylbutylsulfonyl, 3-methylbutylsulfonyl, 1 ,1 -dimethylpropylsulfonyl,

1 .2- dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1 -ethylpropylsulfonyl, hexylsulfonyl, 1 -methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1 ,1 -dimethylbutylsulfonyl, 1 ,2-dimethylbutylsulfonyl,

1 .3- dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,

3,3-dimethylbutylsulfonyl, 1 -ethylbutylsulfonyl, 2-ethylbutylsulfonyl,

1 ,1 ,2-trimethylpropylsulfonyl, 1 ,2,2-trimethylpropylsulfonyl, 1 -ethyl-1 - methylpropylsulfonyl or 1 -ethyl-2-methylpropylsulfonyl. d-Cs-Alkylsulfonyl is additionally, for example, heptylsulfonyl, octylsulfonyl, 2-ethylhexylsulfonyl and positional isomers thereof. Ci-Cio-Alkylsulfonyl is additionally, for example,

nonylsulfonyl, decylsulfonyl and positional isomers thereof. The term "Ci-C2-haloalkylsulfonyl" is a Ci-C2-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci-C3-haloalkylsulfonyl" is a C1-C3- haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term

"Ci-C4-haloalkylsulfonyl" is a Ci-C4-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci-C6-haloalkylsulfonyl" is a Ci-C6-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "C1-C10- haloalkylsulfonyl" is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfonyl [S(0)₂] group. Ci-C₂-Haloalkylsulfonyl is, for example, S(0)₂CH₂F, S(0)₂CHF₂,

S(0)₂CF₃, S(0)₂CH₂CI, S(0)₂CHCI₂, S(0)₂CCI₃, chlorofluoromethylsulfonyl,

dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl,

2.2- difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl,

2.2.2- trichloroethylsulfonyl or S(0)2C2F₅. Ci-C3-Haloalkylsulfonyl is additionally, for example, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl,

2.3- difluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl,

2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl,

3.3.3- trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, S(0)₂CH2-C2F₅, S(0)₂CF₂- C2F5, 1 -(CH₂F)-2-fluoroethylsulfonyl, 1 -(CH₂CI)-2-chloroethylsulfonylor 1 -(CH₂Br)-2- bromoethylsulfonyl. Ci-C4-Haloalkylsulfonyl is additionally, for example,

4- fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or

nonafluorobutylsulfonyl. Ci-C6-Haloalkylsulfonyl is additionally, for example,

5- fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-brompentylsulfonyl,

5-iodopentylsulfonyl, undecafluoropentylsulfonyl, 6-fluorohexylsulfonyl,

6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl or

dodecafluorohexylsulfonyl.

The substituent "oxo" replaces a CH2 group by a C(=0) group. The term "alkylcarbonyl" is a Ci-C6-alkyl ("Ci-C6-alkylcarbonyl"), preferably a C1-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 ("Ci-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 "haloalkoxycarbonyl" is a Ci-C6-haloalkoxy ("Ci-C6-haloalkoxycarbonyl"), preferably a Ci-C4-haloalkoxy ("Ci-C4-haloalkoxycarbonyl") group, as defined above, attached via a carbonyl [C(=0)] group. Examples are trifluoromethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl and the like.

The term "Ci-C6-alkylamino" is a group -N(H)Ci-C6-alkyl. Examples are methylamino, ethylamino, propylamino, isopropylamino, butylamino and the like.

The term "di-(Ci-C6-alkyl)amino" is a group -N(Ci-C6-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 "di-(Ci-C4-alkyl)aminocarbonyl" is a group -N(Ci-C4-alkyl)2. Examples are dimethylaminocarbonyl, diethylaminocarbonyl, ethylmethylaminocarbonyl,

dipropylaminocarbonyl, diisopropylaminocarbonyl, methylpropylaminocarbonyl, methylisopropylaminocarbonyl, ethylpropylaminocarbonyl,

ethylisopropylaminocarbonyl, dibutylaminocarbonyl and the like.

The term "3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring (or heteromonocyclic or heterobicyclic ring) containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members" denotes a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered, preferably a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximum unsaturated heteromonocyclic ring or a 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members. Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond(s). Maximally unsaturated rings contain as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the ring size. Maximally unsaturated 5- or 6-membered heterocyclic rings are aromatic. Partially unsaturated rings contain less than the maximum number of C-C and/or C-N and/or N-N double bond(s) allowed by the ring size. The heterocyclic ring may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. As a matter 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.

The term "3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximum unsaturated heterocyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members" [wherein "maximum unsaturated" includes also "aromatic"] as used herein denotes monocyclic radicals, the monocyclic radicals being saturated, partially unsaturated or maximum unsaturated (including aromatic). The term "3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximum unsaturated heterocyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members" [wherein "maximum unsaturated" includes also "aromatic"] as used herein further also encompasses 8-membered heteromonocyclic radicals containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, the monocyclic radicals being saturated, partially unsaturated or maximum unsaturated (including aromatic). Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond(s). Maximum unsaturated rings contain as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the ring size. Maximum unsaturated 5- or 6-membered heterocyclic rings are aromatic. 7- and 8-membered rings cannot be aromatic. They are homoaromatic (7-membered ring, 3 double bonds) or have 4 double bonds (8-membered ring). The heterocyclic ring may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. As a matter 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.

Examples of a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring include:

Oxiranyl, thiiranyl, aziridinyl, oxetanyl, thietanyl, azetidinyl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1 -yl, pyrrolidin- 2-yl, pyrrolidin-3-yl, pyrazolidin-1 -yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-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, isothiazolidin-4-yl, isothiazolidin-5-yl,

1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4-oxadiazolidin-5-yl, 1 ,2,4-thiadiazolidin-3-yl,

1 ,2,4-thiadiazolidin-5-yl, 1 ,2,4-triazolidin-3-yl, 1 ,3,4-oxadiazolidin-2-yl,

1 ,3,4-thiadiazolidin-2-yl, 1 ,3,4-triazolidin-1 -yl, 1 ,3,4-triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 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, hexahydropyrimidin-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 -dioxothiomorpholin-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 a 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclic ring include: 2,3-dihydrofur-2-yl, 2,3-d ihyd rofur-3-yl , 2,4-dihydrofur-2-yl, 2,4-d ihyd rofur-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-isothiazolin-4-yl, 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-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1 -yl,

4.5- dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl,

2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl,

2.3- dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl,

3.4- dihydrooxazol-4-yl, 3,4-dihydrooxazol-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 tetrahydropyrazinyl, 1 ,3, 5-di- or tetrahydrotriazin-2-yl, 1 ,2, 4-di- or tetrahydrotriazin-3-yl,

2.3.4.5- tetrahydro[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]azepin-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- tetrahydro[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 for a 3-, 4-, 5-, 6- or 7-membered maximally 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, 2-pyridinyl,

3- pyridinyl, 4-pyridinyl, 1 -oxopyridin-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.

In the present invention, the "heterobicyclic rings" contain two rings which have at least one ring atom in common. At least one of the two rings contains a heteroatom or heteroatom group selected from N, O, S, NO, SO and SO2 as ring member. The term comprises condensed (fused) ring systems, in which the two rings have two

neighboring ring atoms in common, as well as spiro systems, in which the rings have only one ring atom in common, and bridged systems with at least three ring atoms in common. Examples for fused systems:

Examples for a 7-, 8-, 9- or 10-membered saturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members are:

Examples for a 8-, 9- or 10-membered partially unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members are:

Examples for a 8-, 9- or 10-membered maximally unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members are:

Examples for spiro-bound 7-, 8-, 9- or 10-membered heterobicyclic rings containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members are

Examples for bridged 7-, 8-, 9- or 10-membered heterobicyclic rings containing 1 , 2 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, ring members are

H

and the like.

In the above structures # denotes the attachment point to the remainder of the molecule. The attachment point is not restricted to the ring on which is shown, but can be on either of the fused rings, and may be on a carbon or on a nitrogen ring atom. If the rings carry one or more substituents, these may be bound to carbon and/or to nitrogen ring atoms (if the latter are not part of a double bond).

Examples for heterobicyclic rings formed by R⁵ and R⁶ together with the nitrogen atom they are bound to (in A³) are the above heterobicyclic systems, which contain however at least one NH as a ring member and in which the attachment point # is on a nitrogen atom of such an NH group (where it replaces the hydrogen atom)

A saturated 3-, 4-, 5-, 6-, 7-, 8- or 9-membered ring, wherein the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from O, S, N, NR¹⁴, NO, SO and SO2 and/or 1 or 2 groups selected from C=0, C=S and C=NR¹⁴ as ring members is either carbocyclic or heterocyclic. Examples are, in addition to the saturated

heteromonocyclic rings mentioned above, carbocyclic rings, such as cyclopropyl, cyclopropanonyl, cyclobutyl, cyclobutanonyl, cyclopentyl, cyclopentanonyl, cyclohexyl, cyclohexanonyl, cyclohexadienonyl, cycloheptyl, cycloheptanonyl, cyclooctyl, cyclooctanonyl, furan-2-onyl, pyrrolidine-2-onyl, pyrrolidine-2,5-dionyl, piperidine-2- only, piperidine-2,6-dionyl and the like.

The remarks made below concerning preferred embodiments of the variables of the compounds of formula I, especially with respect to their substituents A, A¹, A², A³, A⁴, A⁵, B , B², B³, B⁴, B⁵, G¹, G², G³, G⁴, G⁵, L, Z, E, X, R R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R^10a, R^10b, R^10c,R¹¹, R¹², R¹³, R¹⁴, R^14a, R^14b, R¹⁵, R¹⁶, m and n, 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 preferred embodiment, A is A¹ and A¹ is -C(=NR⁷)R⁸, where R⁷ and R⁸ have one of the above general meanings, or, in particular, one of the below preferred meanings.

R⁷ as a radical in the group -C(=NR⁷)R⁸ is preferably selected from hydrogen, cyano, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last- mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted with 1 , 2, 3, 4, 5 or 6, preferably 1 , 2 or 3, in particular 1 , substituents R⁸; and -NR^10aR^10b; where R⁸, R^10a and R^10b have one of the above general meanings, or, in particular, one of the below preferred meanings. More preferably, R⁷ as a radical in the group -C(=N R⁷)R⁸ is -N R^10aR^10b; where R⁸, R^10a and R^10b have one of the above general meanings, or, in particular, one of the below preferred meanings.

In -N R^10aR^10b as a preferred meaning of R⁷ in -C(=N R⁷)R⁸, R^10a and R^10b, independently of each other, are preferably selected from the group consisting of hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Ci-C6-alkylcarbonyl, C1-C6- haloalkylcarbonyl, -C(=0)N(R^14a)R^14b, -C(=S)N(R^14a)R^14b, phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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, e.g. 1 , 2 or 3, in particular 1 , substituents 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 unsaturated or maximally unsaturated

heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-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 and C2-C6-haloalkynyl; wherein R^14a, R^14b and R¹⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings. More preferably, in -N R^10aR^10b as a preferred meaning of R⁷ in -C(=N R⁷)R⁸,

R^10a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl and in particular from hydrogen and Ci-C4-alkyl; and

R ⁰ is selected from -C(=0)N(R ^4a)R ⁴ , -C(=S)N(R ^4a) R ⁴ , Ci-C₄-alkyl, phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, and a 5- or 6-membered heteroaromatic ring comprising 1 , 2 or 3 heteroatoms selected from N , O and S, as ring members, where the heteroaromatic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶;

wherein

each R¹⁶ has one of the above general meanings, or, in particular, one of the below preferred meanings; and is preferably independently selected from the group consisting of halogen, cyano, nitro, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy, Ci-C₄-haloalkoxy, Ci-C₄-alkylthio, Ci-C₄-haloalkylthio, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4- alkynyl and C2-C4-haloalkynyl; and

R^14a and R^14b have one of the above general meanings, or, in particular, one of the below preferred meanings; or

R^10a and R^10b form together with the nitrogen atom they are bonded to a 5- or 6- membered saturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, Ci-C6-alkyl, d-Ce-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 and C2-C6-haloalkynyl.

Specifically, in this more preferred embodiment, in -NR^10aR^10b as a preferred meaning of R⁷ in -C(=NR⁷)R⁸,

R^10a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl; and

R^10b is selected from -C(=0)N(R^14a)R^14b, -C(=S)N(R^14a)R^14b, phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, and a 5- or 6-membered heteroaromatic ring comprising 1 , 2 or 3 heteroatoms selected from N, O and S, as ring members, where the heteroaromatic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶;

wherein

each R¹⁶ has one of the above general meanings, or, in particular, one of the below preferred meanings; and is preferably independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4- alkynyl and C2-C4-haloalkynyl; and

R^14a and R^14b have one of the above general meanings, or, in particular, one of the below preferred meanings.

Even more preferably, in -NR^10aR^10b as a preferred meaning of R⁷ in -C(=NR⁷)R⁸, R^10a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl, and in particular from hydrogen and Ci-C4-alkyl; and

R ⁰ is selected from -C(=0)N(R ^4a)R ⁴ and -C(=S)N(R ^4a)R ⁴ ;

wherein

R^14a and R^14b have one of the above general meanings, or, in particular, one of the below preferred meanings; or R^10a and R^10b form together a group -(Chbjp-, where p is 4 or 5.

If R^10b in -NR^10aR^10b as a preferred meaning of R⁷ in -C(=NR⁷)R⁸ is selected from -C(=0)N(R ^4a)R ^4b and -C(=S)N(R ^4a)R ⁴ ; preferably

R^14a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl; and

R^14b is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, phenyl which is optionally substituted with 1 , 2, 3 or 4 substituents each independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; and a heterocyclic ring selected from rings of formulae E-1 to E-51

E-1 E-2 E-3 E-4 E-5

E-6 E-7 E-8 E-9

E-10 E-1 1 E-12 E-13 E-14

E-15 E-16 E-17 E-18 E-19

E-20 E-21 E-22 E-23 E-24

E-25 E-26 E-27 E-28 E-29

E-30 E-31 E-32 E-33 E-34

E-40 E-41 E-42 E-43 E-44

E-45 E-46 E-47 E-48 E-49

E-51 wherein denotes the bonding point to the remainder of the molecule;

k is 0, 1 , 2 or 3,

q is 0, 1 or 2; each R^16a is independently hydrogen or has one of the meanings given below for R¹⁶; and

each R¹⁶ is independently selected from the group consisting of halogen,

cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl,

C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or two R¹⁶ present on the same carbon atom of a saturated ring may form together =0 or =S. More preferably, in the above radicals R^10a and R^10b,

R^14a is selected from hydrogen and methyl and is specifically hydrogen; and

R^14b is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-methyl-, where the cycloalkyi moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, and a 4-membered saturated heterocyclic ring comprising one heteroatom or heteroatom group selected from S, SO and SO2 as ring member (ring E-44), where the heterocyclic ring is optionally substituted with one or more, preferably 1 or 2, in particular 1 , substituents R¹⁶;

wherein each R¹⁶ is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or

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

In an alternatively more preferred embodiment, in the above radicals R^10a and R^10b, R^14a is selected from hydrogen and Ci-C4-alkyl, preferably from hydrogen and methyl, and is specifically hydrogen; and

R^14b is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl-Ci-C4- alkyl-, where the cycloalkyi moieties in the last-mentioned radical may carry a CN group; Ci-C4-alkyl substituted with a CN group, Ci-C4-alkoxy and C1-C4- haloalkoxy.

In an alternative, even more preferred embodiment, in -NR^10aR^10b as a preferred meaning of R⁷ in -C(=NR⁷)R⁸,

R^10b is selected from Ci-C4-alkyl and a 5- or 6-membered heteroaromatic ring

comprising 1 , 2 or 3 heteroatoms selected from N, O and S, as ring members, where the heteroaromatic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶; and preferably from Ci-C4-alkyl and a 6- membered heteroaromatic ring comprising 1 or 2, preferably 1 , nitrogen ring atoms.

Preferably, in the above radicals, each R¹⁶ is independently selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

R⁸ as a radical in the group -C(=NR⁷)R⁸ is preferably selected from hydrogen, C1-C4- alkyl, Ci-C4-haloalkyl and -N(R^10a)R^10b, and more preferably from hydrogen and

-N(R^10a)R^10b, and is specifically hydrogen.

In this case (i.e. in -N(R^10a)R^10b as a meaning of R⁸), R^10a and R^10b are preferably selected, independently of each other, from the group consisting of hydrogen, C1-C6- alkyl, d-Ce-haloalkyl, C2-Ce-alkenyl, C2-Ce-haloalkenyl, C2-Ce-alkynyl, C2-C6- haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Ci-C6-alkylcarbonyl, C1-C6- haloalkylcarbonyl,

-C(=0)N(R^14a)R¹⁴ , -C(=S)N(R^14a)R¹⁴ , phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, and a 3-, 4-, 5-, 6- or

7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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, e.g. 1 , 2 or 3, in particular 1 , substituents 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 unsaturated or maximally unsaturated

heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-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 and C2-C6-haloalkynyl; wherein R^14a, R^14b and R¹⁶ have one of the above general meanings, or, in particular, one of the above preferred meanings. More preferably, R^10a and R^10b are in this case selected, independently of each other, from hydrogen, 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-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C4-haloalkylaminocarbonyl, C3-C6-cycloalkylaminocarbonyl and C3-C6-halocycloalkylaminocarbonyl, or, 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, where the heterocyclic ring may carry 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 C1-C4- haloalkylthio. Even more preferably, R^10a and R^10b are in this case selected, independently of each other, from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, Ci-C4-alkylaminocarbonyl and Ci-C4-haloalkylaminocarbonyl; and are specifically hydrogen or Ci-C6-alkyl.

In an alternatively more preferred embodiment of the invention, A¹ is

-C(=NOR⁹)N(R^10a)R^10c, where R⁹, R^10a and R^10c have one of the above general meanings, or, in particular, one of the below preferred meanings.

Preferably, R⁹ in -C(=NOR⁹)N(R^10a)R^10c as a meaning for A¹ is selected from Ci-C₆- alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl-, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl, and preferably from Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl and C3-C8-cycloalkyl-Ci-C4-alkyl-; and R^10a and R^10c have one of the above general meanings, or, in particular, one of the below preferred meanings.

Preferably, in -C(=NOR⁹)N(R^10a)R^10c as a meaning for A¹,

R^10a is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, -C(=0)N(R^14a)R^14b, -C(=S)N(R^14a)R^14b, phenyl which is optionally substituted with

1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶; and

R^10c is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, -C(=0)N(R^14a)R^14b, -C(=S)N(R^14a)R^14b, phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶;

wherein R^14a, R^14b and R¹⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings.

More preferably, in -C(=NOR⁹)N(R^10a)R^10c as a meaning for A¹,

R⁹ is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl, and preferably from Ci-C6-alkyl, C1-C6- haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl and

C3-Cs-cycloa I kyl-C-i -C₄-a I kyl-;

R^10a is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, -C(=0)N(R^14a)R^14b, -C(=S)N(R^14a)R¹⁴ , phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶; and

R^10c is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl,

-C(=0)N(R^14a)R¹⁴ , -C(=S)N(R^14a)R¹⁴ , phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶;

wherein R^14a, R^14b and R¹⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings. Preferably, in the above radicals R^10a and R^10c,

R^14a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl; and

R^14b is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyi moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents each independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4- haloalkynyl; and a heterocyclic ring selected from rings of formulae E-1 to E-51 (see above); and

each R¹⁶ is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or

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

More preferably, in the above radicals R^10a and R^10c,

R^14a is selected from hydrogen and methyl and is specifically hydrogen; and

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

In particular, in the above radicals, each R¹⁶ is independently selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy. In an alternatively preferred embodiment, A is A².

In A², W¹ is preferably O. M is preferably

where R⁹ and m have one of the above general meanings, or, in particular, one of the below preferred meanings.

Preferably, in

as a meaning for M, each R⁹ is independently selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-C8- cycloalkyl-Ci-C4-alkyl-, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R¹³, phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶; 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, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶, or

two R⁹ in the group

may form together with the sulfur atom they are bonded to a 4-, 5-, or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N , O, S, NO, SO, SO2, C(=S) and C(=0) as ring members, where the heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl;

wherein R¹³ and R¹⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings.

More preferably, in

as a meaning for M, each R⁹ is independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-C8- cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, and phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, or

two R⁹ in the group

form together with the sulfur atom they are bonded to a 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, C(=S) and C(=0) as ring members, where the heterocyclic ring optionally carries one or two, in particular 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl; wherein each R¹⁶ is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or

two R¹⁶ present on the same carbon atom may form together a group =0 or =S, and wherein preferably each R¹⁶ is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

Even more preferably, in

as a meaning for M, each R⁹ is independently selected from Ci-C6-alkyl, or

two R⁹ in the group

In particular, in

as a meaning for M, each R⁹ is independently selected from Ci-C6-alkyl, or

the two R⁹ in the group

form together a group -(Chb - where r is 4 or 5. m is preferably 0 or 1 and is in particular 0.

In alternatively preferred embodiment, M is

where R⁹ has one of the above general meanings, or, in particular, one of the below preferred meanings. Preferably, in

as a meaning for M, each R⁹ is independently selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3- C8-cycloalkyl-Ci-C4-alkyl-, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R¹³, phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶; 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, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶, or

two R⁹ in the group

may form together with the sulfur atom they are bonded to a 4-, 5-, or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, C(=S) and C(=0) as ring members, where the heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl;

wherein R¹³ and R¹⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings. More preferably, in

as a meaning for M, each R⁹ is independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3- C8-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, and phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, or

two R⁹ in the group

Even more preferably, in

as a meaning for M, each R⁹ is independently selected from Ci-C6-alkyl, or

two R⁹ in the group

form together with the sulfur atom they are bonded to a 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, in particular a saturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, C(=S) and C(=0) as ring members, where the heterocyclic ring optionally carries one or two, in particular 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-a I kynyl , C2-C6-hal oa I kynyl ;

wherein each R¹⁶ is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or

In particular, in

as a meaning for M, each R⁹ is independently selected from Ci-C6-alkyl, or

the the two R⁹ in the group =S(NR^10a)(R⁹)₂ form together a group -(CH₂)_r- where r is 4 or 5.

Preferably, in

as a meaning for M, R^10a is selected from hydrogen, Ci- C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Ci-C6-alkylcarbonyl, C1-C6- haloalkylcarbonyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, phenyl which is optionally substituted with 1 , 2, 3 or 4 substituents R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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 substituents R¹⁶; where R¹⁶ has one of the above general, or, in particular, one of the below preferred meanings. More preferably, R^10a is selected from hydrogen and C1-C6- alkyl.

In alternatively preferred embodiment, M is

where R⁸ has one of the above general meanings, or, in particular, one of the below preferred meanings.

Preferably, in

as a meaning of M, each R⁸ is independently selected from d-Ce-alkyl, Ci-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆- haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, where the aliphatic and

cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R¹³; phenyl, optionally substituted with 1 , 2, 3, 4 or 5, prefeably 1 , 2 or 3, in particular 1 , substituents R¹⁶, 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, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶, wherein R¹³ and R¹⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings; or

the two radicals R⁸ in the group

together with the carbon atom they are bound to , form a 5- or 6-membered saturated carbocyclic or heterocyclic ring, where the heterocyclic ring comprises 1 , 2 or 3 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, and where the carbocyclic or heterocyclic ring is optionally substituted with one or more substituents R¹⁶, wherein R¹⁶ has one of the above general meanings, or, in particular, one of the below preferred meanings.

In the above radical R⁸, each R¹³ is independently preferably selected from the group consisting of cyano, nitro, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, C3-C6-cycloalkyl and C3-C6-halocycloalkyl; where R¹³ as a substituent on a cycloalkyl moiety is additionally selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl.

In the above radical R⁸, each R¹⁶ is independently preferably selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or

two R¹⁶ present on the same carbon atom may form together a group =0 or =S, and more preferably from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy. If R¹⁶ is bound to a nitrogen atom, it is preferably selected from Ci- C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl, more preferably from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, and is specifically Ci-C4-alkyl.

More preferably, in

as a meaning of M, each R⁸ is independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkyl- Ci-C4-alkyl-, where the cycloalkyl moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, and phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, wherein each R¹⁶ is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or

two R¹⁶ present on the same carbon atom may form together a group =0 or =S, and wherein preferably each R¹⁶ is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or

two radicals R⁸ in the group

together with the carbon atom they are bound to , form a 5- or 6-membered saturated carbocyclic or heterocyclic ring, where the heterocyclic ring comprises 1 , 2 or 3 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, and where the carbocyclic or heterocyclic ring is optionally substituted with one or more substituents R¹⁶; wherein R¹⁶ has one of the above general meanings, or, in particular, one of the below preferred meanings.

In particular, in

as a meaning of M, the two radicals R⁸, together with the carbon atom they are bound to, form a 5- or 6-membered saturated heterocyclic ring, where the heterocyclic ring comprises 1 or 2 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2, preferably from N and S, as ring members, and where the heterocyclic ring is optionally substituted with one or more substituents R¹⁶; wherein R¹⁶ has one of the above general meanings, or, in particular, one of the below preferred meanings.

In an alternatively preferred embodiment, A is A³.

In A³, W² is preferably O. In A³, R⁵ is preferably -S(O)_q(=NR^10a)_pR⁹, where q and p are 0 (in other words: R⁵ is preferably -SR⁹).

In

as a meaning for R⁵, where q and p are 0, R⁹ is preferably selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4- alkyl-, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R¹³, phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶; 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, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶; wherein R¹³ and R¹⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings.

In the above radical R⁹, each R¹³ is independently preferably selected from the group consisting of cyano, nitro, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, C3-C6-cycloalkyl and C3-C6-halocycloalkyl; where R¹³ as a substituent on a cycloalkyl moiety is additionally selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl.

In the above radical R⁹, each R¹⁶ is independently preferably selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or

two R¹⁶ present on the same carbon atom may form together a group =0 or =S, and more preferably from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

More preferably, in -S(O)_q(=NR^10a)_pR⁹ as a meaning for R⁵, where q and p are 0, R⁹ is selected from Ci-C6-alkyl, Ci-C6-haloalkyl and a 5-, 6- or 7-membered saturated 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, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶; wherein each R¹⁶ is independently preferably selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or two R¹⁶ present on the same carbon atom may form together a group =0 or =S, and more preferably from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and

Ci-C4-haloalkoxy. In an alternatively preferred embodiment, R⁵ in A³ is -SO2[N(R^10a)R^10b].

In -SO2[N(R^10a)R^10b] as a meaning for R⁵, R^10a and R^10b are independently of each other selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, Ci-C₆-alkylcarbonyl, Ci-C₆-haloalkylcarbonyl, -C(=0)N(R^14a)R^14b,

-C(=S)N(R^14a)R^14b, phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶;

heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-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 and C2-C6-haloalkynyl; wherein R^14a, R^14b and R¹⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings.

Preferably, in the above radicals R^10a and R^10b,

R^14a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl; and

R^14b is selected from hydrogen, d-C₆-alkyl, Ci-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents each independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4- haloalkynyl; and a heterocyclic ring selected from rings of formulae E-1 to E-51 (see above); and

two R¹⁶ present on the same carbon atom of a saturated ring may form together =0 or =S. More preferably, in the above radicals R^10a and R^10b,

R^14a is selected from hydrogen and methyl and is specifically hydrogen; and

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

In particular, in the above radicals, each R¹⁶ is independently selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

More preferably, R^10a and R^10b in -SO2[N(R^10a)R^10b] as a meaning for R⁵ are

independently of each other hydrogen or Ci-C6-alkyl and are in particular

independently of each other Ci-C6-alkyl.

In an alternatively preferred embodiment, R⁵ in A³ is -S(O)_q(=NR^10a)_pR⁹, where q is 0 and p is 1 (or, expressed alternatively, R⁵ is -S(=NR^10a)R⁹), and where

R⁹ is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C8- cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R¹³, phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶; 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, e.g. 1 , 2 or

3, in particular 1 , substituents R¹⁶; and

R^10a is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C8- cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R¹³;

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

a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶;

wherein n, R¹³, R^14a, R^14b, R¹⁵ and R¹⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings.

In the above radicals R⁹ and R^10a, each R¹³ is independently preferably selected from the group consisting of cyano, nitro, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl and C3-C6-halocycloalkyl; where R¹³ as a substituent on a cycloalkyl moiety is additionally selected from Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl.

In the above radicals R⁹ and R^10a, each R¹⁵ is independently preferably selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may be unsubstituted and/or carry 1 , 2 or 3, preferably 1 or 2, in particular 1 , substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy; and is in particular Ci-C6-alkyl. In the above radicals R⁹ and R^10a, each R¹⁶ is independently preferably selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or two R¹⁶ present on the same carbon atom may form together a group =0 or =S, and more preferably from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and

Ci-C4-haloalkoxy.

Preferably, in the above radical R^10a,

R^14a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl; and

R^14b is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyi moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents each independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4- haloalkynyl; and a heterocyclic ring selected from rings of formulae E-1 to E-51 (see above).

More preferably, in the above radicals R^10a and R^10b,

R^14a is selected from hydrogen and methyl and is specifically hydrogen; and

two R¹⁶ present on the same carbon atom may form together a group =0 or =S. More preferably, in -S(O)_q(=NR^10a)_pR⁹ as a meaning for R⁵ in A³, wherein q is 0 and p is 1 ,

R⁹ is d-Ce-alkyl; and

R^10a is -S(0)₂R¹⁵, wherein R¹⁵ is Ci-C₆-alkyl. In an alternatively preferred embodiment, R⁵ in A³ is -P(=0)(OR⁹)₂ or -P(=S)(OR⁹)₂.

In -P(=0)(OR⁹)₂ and -P(=S)(OR⁹)₂ as a meaning for R⁵, preferably

each R⁹ is independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C8- cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, Cs-Cs-halocycloalkyl, C₂-C6-alkenyl, C₂-

C6-haloalkenyl, C₂-C6-alkynyl, C₂-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R¹³, phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶; 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 S0₂ as ring members, where the heterocyclic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶; and is preferably Ci-C6-alkyl; wherein each R¹³ is independently selected from the group consisting of cyano, nitro, Ci-

C₄-alkoxy, Ci-C₄-haloalkoxy, Ci-C₄-alkylthio, Ci-C₄-haloalkylthio, C3-C6- cycloalkyl and C3-C6-halocycloalkyl; where R¹³ as a substituent on a cycloalkyl moiety is additionally selected from Ci-C₄-alkyl, Ci-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; and each R¹⁶ is independently selected from the group consisting of halogen,

cyano, nitro, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₄-alkoxy, Ci-C₄-haloalkoxy, Ci-C₄-alkylthio, Ci-C₄-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; or two R¹⁶ present on the same carbon atom may form together a group =0 or =S.

In A³, independently of the meaning of R⁵, R⁶ is preferably selected from the group consisting of hydrogen, Ci-C₄-alkyl, C₂-C3-alkynyl, -CH₂-CN and Ci-C6-alkoxy-methyl-, and preferably from hydrogen and Ci-C₄-alkyl.

In an alternatively preferred embodiment, in A³, R⁵ and R⁶, together with the nitrogen atom to which they are bound, form a 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring, where the ring may further contain 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, S0₂, C=0 and C=S as ring members, wherein the heterobicyclic ring may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyI, Cs-Cs-halocycloalkyl, C₂-C6-alkenyl, C₂-C6-haloalkenyl, C₂-C6-alkynyl, C2-C6-haloalkynyl, wherein the aliphatic or cycloaliphatic moieties in the twelve last- mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R⁸, and phenyl which may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹¹; wherein R⁸ and R¹¹ have one of the above general or, in particular, one of the below preferred meanings.

Suitable heterobicyclic rings formed by N, R⁵ and R⁶ are for example the following:

74

wherein # denotes the attachment point to C(=W²). Rings containing two nitrogen ring atoms show the attachment point unlocalized. In this case, the attachment point is localized on either one of the two nitrogen ring atoms.

These heterobicyclic rings may carry 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, in particular 1 , substituents R¹⁷, wherein each R¹⁷ has independently one of the above general, or in particular, one of the below preferred meanings.

Preferably, R¹⁷ is selected from the group consisting of halogen, cyano, nitro, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl, or two radicals R¹⁷ present on the same carbon atom of a saturated ring may form together a group =0 or =S, and more preferably from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, or two radicals R¹⁷ present on the same carbon atom of a saturated ring may form together a group =0.

Among the above heterobicyclic rings, prefe

wherein

# denotes the attachment point to C(=W²);

k is 0, 1 , 2, 3, 4 or 5, preferably 0, 1 , 2 or 3, more preferably 1 or 2, in particular 0 or 1 ;

q is 0, 1 or 2; and

each R¹⁷ independently has one of the above general meanings or is preferably 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, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4- alkynyl and C2-C4-haloalkynyl, or two radicals R¹⁷ present on the same carbon atom of a saturated ring may form together a group =0 or =S, and more preferably from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and

Ci-C4-haloalkoxy, or two radicals R¹⁷ present on the same carbon atom of a saturated ring may form together a group =0.

The attachment point of the radical(s) R¹⁷ is not restricted to the ring on which is shown, but can be on either of the fused rings, and may be on a carbon or on a nitrogen ring atom (if the latter is not part of a double bond).

More preference is iven to following

#-N #-N O #-N SCL

In an alternatively preferred embodiment, A is A⁴.

Preferably, A⁴ is selected from rings of formulae D-1 to D-184

D-1 D-2 D-3 D-4 D-5

D-6 D-7 D-8 D-9 D-10 

_Hs

D-45 D-46 D-47 D-48 D-49

D-50 D-51 D-52 D-53 D-54

D-55 D-56 D-57 D-58 D-59

D-60 D-61 D-62 D-63 -64

D-68 D-69 D-70 D-71 D-72

D-73 D-74 D-75 D-76 D-77

D-111 D-112 D-113 D-114 D-115

1)_k R^S

D-116 D-117 D-118 D-119 D-120

D-121 D-122 D-123 D-124 D-125

1¹)_k

D-126 D-127 D-128 D-129 D-130

D-131 D-132 D-133 D-134 D-135

D-136 D-137 D-138 D-139 D-140

D-141 D-142 D-143 D-144 D-145

D-181 D-182 D-183 D-184 wherein denotes the bonding point to the remainder of the molecule,

k is 0, 1 , 2 or 3;

q is 0, 1 or 2;

R¹¹ has one of the above general meanings or, in particular, one of the below

preferred meanings;

R^11a is hydrogen or has one of the above general meanings or, in particular, one of the below preferred meanings given for R¹¹, where however R^11a is not halogen; and

R^s is SH or =S;

More preferably, A⁴ is selected from D-59, D-63 and D-64 and is in particular D-59.

Preferably, in A⁴, each R¹¹ is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or

two R¹¹ present on the same carbon atom may form together a group =0 or =S.

More preferably, each R¹¹ is independently selected from halogen, CN , Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, or two R¹⁶ present on the same carbon atom may form together a group =0 or =S. Specifically, two R¹⁶ present on the same carbon atom form together a group =S.

Preferably, in A⁴, each R^11a is independently selected from hydrogen and Ci-C4-alkyl. k is preferably 0 or 1 and specifically 0. specifically

or its tautomer. In an alternatively preferred embodiment, A is A⁵. A⁵ is preferably -NR ^0a-NR ^0b-C(=O)R⁸.

Preferably, in A⁵,

R^10a and R^10b, independently of each other, are selected from hydrogen and C1-C6- alkyl; and

R⁸ is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R¹³;

-N(R^10a)R^10b, phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, 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, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶,

wherein R¹³ and R¹⁶ have one of the above general meanings, or in particular, one of the below preferred meanings.

Preferably, in the above radical R⁸, R^10a and R^10b are selected, independently of each other, from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R¹³; and phenyl, where R¹³ is selected from CN, Ci-C4-alkoxy, Ci-C4-alkylthio and phenyl. More preferabyl, R^10a and R^10b are selected, independently of each other, from hydrogen, d-Ce-alkyl, Ci-C₆-haloalkyl, CH₂CN, CH₂-S-Ci-C₄-alkyl, benzyl and phenyl.

More preferably, in A⁵,

R⁸ is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R¹³; phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R¹⁶, 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, e.g. 1 , 2 or 3, in particular 1 , substituents R¹⁶,

Preferably, in the above radical R⁸, each R¹³ is independently selected from the group consisting of cyano, nitro, 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 and C3-C6-halocycloalkyl; where R¹³ as a substituent on a cycloalkyl moiety is additionally selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl. Preferably, in the above radical R⁸, each R¹⁶ is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or

two R¹¹ present on the same carbon atom may form together a group =0 or =S.

More preferably, each R¹⁶ is independently selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

In a preferred embodiment, B¹ and B⁵ are CH and B², B³ and B⁴ are CR², where R² has one of the above general meanings, or, in particular, one of the below preferred meanings.

More preferably, B¹ and B⁵ are CH, B² is CR², where R² is not hydrogen, and B³ and B⁴ are CR², where R² has one of the above general meanings, or, in particular, one of the below preferred meanings.

Preferably, R² is selected from hydrogen, halogen, cyano, azido, nitro, -SCN, -SF₅, Ci-C6-alkyl, C3-C₀-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last- mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R⁸, -OR⁹, -S(0)_nR⁹ and -N(R^10a)R^10b, wherein R⁸, R⁹, R^10a and R^10b have one of the above general meanings, or, in particular, one of the below preferred meanings. More preferably, R² is selected from hydrogen, halogen and Ci-C2-haloalkyl, preferably from hydrogen, F, CI, Br and CF3, in particular from hydrogen, CF3, F and CI, and specifically from hydrogen, CF3 and CI. Specifically, B¹ and B⁵ are CH, B² is CR², where R² is selected from CF3, F and CI, and specifically from CF3 and CI, and B³ and B⁴ are CR², where R² is selected from hydrogen, CF3, F and CI and specifically from hydrogen, CF3 and CI.

Preferably, G¹, G⁴ and G⁵ are C-R⁴; and G² and G³ are C-A or C-R⁴; with the proviso that one of G² and G³ is C-A.

More preferably, G¹, G⁴ and G⁵ are C-H; and G² and G³ are C-A or C-R⁴; with the proviso that one of G² and G³ is C-A. Specifically, G¹, G⁴ and G⁵ are C-H; and G² and G³ are C-A or C-R⁴, where R⁴ is different from hydrogen; with the proviso that one of G² and G³ is C-A. This is of course only possible for the case that E and R⁴ do not form a ring.

Preferably, G³ is C-A in case that A is A¹, A², A³ or A⁴, and G² is C-A in case that A is A⁵. This is especially preferred for the case that E and R⁴ do not form a ring.

In particular, G¹, G⁴ and G⁵ are CH; and in case that G³ is C-A, G² is C-R⁴; and in case that G² is C-A, G³ is C-R⁴. Specifically, G¹, G⁴ and G⁵ are CH; and in case that G³ is C-A, G² is C-R⁴, where R⁴ is different from hydrogen; and in case that G² is C-A, G³ is C-R⁴, where R⁴ is different from hydrogen. This is of course only possible for the case that E and R⁴ do not form a ring.

R⁴ is preferably selected from hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C5-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkyl, Ci-C4-haloalkyl,, Ci-C6-alkoxy-Ci-C6-alkyl-, C1-C4- alkylthio and Ci-C4-haloalkylthio, more preferably from hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, even more preferably from hydrogen, CI, methyl, CF3 and methoxy, specifically from hydrogen, CI, CF3 and methoxy and very spefically from hydrogen and CF3. If R⁴ is different from hydrogen, it is preferably selected from halogen, cyano, C1-C4- alkyl, Ci-C4-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkyl, Ci-C4-haloalkyl,, C1-C6- alkoxy-Ci-C6-alkyl-, Ci-C4-alkylthio and Ci-C4-haloalkylthio, and more preferably from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy. If R⁴ is different from hydrogen, it is specifically CI, methyl, CF3 or methoxy and very specifically CF3.

Preferably, R¹ is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl C3-C6-halocycloalkyl or C1-C4- alkoxycarbonyl, more preferably, from Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and Ci-C4-alkoxycarbonyl, even more preferably from Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxycarbonyl, and particularly preferably from C1-C4- haloalkyl and Ci-C4-alkoxycarbonyl. In particular, R¹ is Ci-C4-haloalkyl, specifically Ci-C2-haloalkyl and more specifically halomethyl, in particular fluoromethyl, such as fluoromethyl, difluoromethyl and trifluoromethyl, and is very specifically trifluoromethyl.

Preferably, L is selected from hydrogen and Ci-C4-alkyl, and is more preferably hydrogen.

Preferably, E is selected from hydrogen, halogen and Ci-C4-alkyl, and is more preferably hydrogen.

In an alternatively preferred embodiment, E and a radical R⁴ bound in the position of G¹ or G⁵, together with the carbon atoms they are bound to, form a 5-, 6-, or 7-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO2, C=0 and C=S as ring members, wherein the ring may be substituted with 1 , 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl and Ci-C6-alkoxy. More preferably, E and a radical R⁴ bound in the position of G¹ or G⁵, together with the carbon atoms they are bound to, form a 5- or 6-membered heteroaromatic ring, where the ring contains 1 or 2 heteroatoms selected from O, S and N, preferably N, wherein the ring may be substituted with 1 or 2 substituents independently selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl and Ci-C6-alkoxy. Specifically, E and a radical R⁴ bound in the position of G¹ or G⁵, together with the carbon atoms they are bound to, form a 5-membered heteroaromatic ring, where the ring contains 1 nitrogen ring atom, wherein the ring may be substituted with 1 or 2 substituents independently selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl and Ci-C6-alkoxy.

Preferably, X is selected from hydrogen, halogen and Ci-C4-alkyl, and is more preferably hydrogen. Preferably, R³ is selected from hydrogen, Ci-C4-alkyl, C2-C3-alkynyl, -CH2-CIM and Ci-C6-alkoxy-methyl-, more preferably from hydrogen and Ci-C4-alkyl and is specifically hydrogen. Z is preferably O.

If not specified otherwise above, R⁸, R⁹, R^10a, R^10b, R^10c, R¹¹, R¹², R¹³, R¹⁴, R^14a, R^14b, 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 ^0a)R ^0b, -C(=S)N(R ^0a)R ^0b, -C(=0)OR⁹, phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , 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 heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals 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 an alkyl, alkenyl or alkynyl group, it is even more preferably selected from the group consisting of cyano, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, -C(=O)N(R ^0a)R ⁰ , -C(=S)N(R ^0a)R ⁰ , -C(=0)OR⁹, phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , 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 heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals 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 particular it is selected from the group consisting of cyano, C3-C6-cycloalkyl, C3-C6- halocycloalkyl,

-C(=O)N(R ^0a)R ⁰ , -C(=S)N(R ^0a)R ⁰ , -C(=0)OR⁹, phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , 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 heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals 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 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 ^0a)R ^0b, -C(=O)N(R ^0a)R ^0b, -C(=S)N(R ^0a)R ^0b, -C(=0)OR⁹ , phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , 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 heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals 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 halogen, 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 halogen, Ci-C4-alkyl and Ci-C3-haloalkyl.

In case of R⁸ in a group -C(=0)R⁸, =C(R⁸)₂ or -C(=NR⁶)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, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, -OR⁹, -SR⁹, -N(R^10a)R¹⁰ , phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , 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 heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals 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 of R⁸ in a group -C(=0)R⁸, =C(R⁸)₂ or -C(=NR⁶)R⁸, R⁸ is more preferably selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Ci-C₆-alkoxy, Ci-C₆-haloalkoxy, -N(R^10a)R¹⁰ , phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , 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 heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R¹⁶; where 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 hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkyl- Ci-C4-alkyl, phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , 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 heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1 , 2, 3 or 4, preferably 1 , 2 or 3, more preferably 1 or 2, in particular 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 may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals 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 may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R¹⁶; where R¹⁶ has one of the meanings given above or in particular one of the preferred meanings given below. 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-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkylcarbonyl, C1-C4- haloalkylcarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C4-haloalkylaminocarbonyl, C3-C6- cycloalkylaminocarbonyl, C3-C6-halocycloalkylaminocarbonyl, 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, e.g. 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, Ci-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, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, CN , Ci-C4-alkyl, C1-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 hydrogen, 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, e.g. 1 , 2 or 3, in particular 1 , substituents selected from halogen, CN , Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy; and are specifically, independently of each other, selected from hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl.

R^10c is preferably selected from 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-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkylaminocarbonyl, C1-C4- haloalkylaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, C3-C6- halocycloalkylaminocarbonyl, 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, e.g. 1 , 2 or 3, in particular 1 , substituents selected from halogen, CN , Ci-C4-alkyl, C1-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;

or, R^10a and R^10c, 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, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, CN , Ci-C4-alkyl, C1-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^10c is selected from 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, e.g. 1 , 2 or 3, in particular 1 , substituents selected from halogen, CN , Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; and is specifically selected from C1-C4- alkyl and 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, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, C1-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 the group consisting of cyano, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, -OH, -SH, Ci-C₄-alkoxy, Ci-C₄-haloalkoxy, Ci-C₄-alkylthio, Ci-C₄-haloalkylthio, C1-C4- alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl and phenyl which may be substituted by 1 , 2 or 3 radicals selected from halogen, C1-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 the group consisting of cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs- halocycloalkyl, -OH, -SH, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, C1-C4- haloalkylsulfonyl and phenyl which may be substituted by 1 , 2 or 3, in particular 1 , radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy.

In case R¹³ is a substituent on a cycloalkyl group, it is even more preferably selected from the group consisting of 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(R¹³)₂ or -C(=NR⁴)R¹³, R⁸ is preferably selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, -OH, -SH, Ci-C6-alkoxy, Ci-C6-haloalkoxy and phenyl which may be substituted by 1 , 2 or 3, in particular 1 , 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 hydrogen, 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, 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 additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

More preferably, R¹⁴, R^14a and R^14b are, independently of each other, selected from hydrogen, Ci-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 additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy. Each R¹⁵ is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may be unsubstituted and/or carry 1 , 2 or 3, in particular 1 , substituents selected from C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy. Each R¹⁶ is preferably selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or

two R¹¹ present on the same carbon atom may form together a group =0 or =S.

Each R¹⁷ is preferably selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl, or two radicals R¹⁷ present on the same carbon atom of a saturated ring may form together a group =0 or =S, and more preferably from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, or two radicals R¹⁷ present on the same carbon atom of a saturated ring may form together a group =0.

In a particular embodiment, the invention relates to a compound of formula I.A or I.B

I.A I.B

wherein

A^a is A¹, A², A³ or A⁴;

R^2a, R^2b and R^2c, independently of each other, have one of the general, or in particular, one of the preferred meanings given above for R²; and

R³, R⁴, A¹, A², A³, A⁴ and A⁵ have one of the general, or in particular, one of the

preferred meanings given above.

In lates to a compound of formula I.C

A^a is A¹, A², A³ or A⁴;

R^2a, R^2b and R^2c, independently of each other, have one of the general, or in particular, one of the preferred meanings given above for R²;

preferred meanings given above and

R^N is selected from the group of Ci-C6-alkyl, Ci-C6-haloalkyl and Ci-C6-alkoxy, and is in particular Ci-C6-alkyl.

Examples of preferred compounds are compounds of the following formulae 1.1 to 1.42 and their tautomers (especially of compounds 1.30 to 1.32), where R^2a, R^2b and R^2c have one of the general or one of the preferred meanings given above for R², R^9a and R^9b have one of the general or one of the preferred meanings given above for R⁹ (except for compound 1.10, where R^9a and R^9b have one of the general or one of the preferred meanings given above for R⁸) and the other variables have one of the general or preferred meanings given above. Examples of preferred compounds are the individual compounds compiled in the tables 1 to 1616 below. Moreover, the meanings mentioned below for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.

(1.10) 96

97

Table 1

Compounds of the formula 1.1 in which R^14b is hydrogen, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 2

Compounds of the formula 1.1 in which R^14b is methyl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 3

Compounds of the formula 1.1 in which R^14b is ethyl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 4

Compounds of the formula 1.1 in which R^14b is propyl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 5

Compounds of the formula 1.1 in which R^14b is isopropyl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 6

Compounds of the formula 1.1 in which R^14b is n-butyl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 7

Compounds of the formula 1.1 in which R^14b is sec-butyl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 8

Compounds of the formula 1.1 in which R^14b is isobutyl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 9

Compounds of the formula 1.1 in which R^14b is tert-butyl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 10

Compounds of the formula 1.1 in which R^14b is propargyl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 1 1

Compounds of the formula 1.1 in which R^14b is cyclopropyl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 12

Compounds of the formula 1.1 in which R^14b is 1 -cyanocycloprop-1 -yl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 13

Compounds of the formula 1.1 in which R^14b is 2,2-difluoroethyl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 14

Compounds of the formula 1.1 in which R^14b is 2,2,2-trifluoroethyl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 15

Compounds of the formula 1.1 in which R^14b is Chb-CN, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 16

Compounds of the formula 1.1 in which R^14b is Chb-cyclopropyl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 17

Compounds of the formula 1.1 in which R^14b is CH2-(1 -cyanocycloprop-1 -yl), and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 18

Compounds of the formula 1.1 in which R^14b is thietan-3-yl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 19

Compounds of the formula 1.1 in which R^14b is 1 -oxo-thietan-3-yl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 20

Compounds of the formula 1.1 in which R^14b is 1 ,1 -dioxo-thietan-3-yl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 21

Compounds of the formula 1.1 in which R^14b is methoxy, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 22

Compounds of the formula 1.1 in which R^14b is ethoxy, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 23

Compounds of the formula 1.1 in which R^14b is n-propoxy, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 24

Compounds of the formula 1.1 in which R^14b is 2,2-difluoroethoxy, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 25

Compounds of the formula 1.1 in which R^14b is 2,2,2-trifluoroethoxy, and the

combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 26 to 50

Compounds of the formula 1.2 in which R^14b is as defined in any of tables 1 to 25 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 51 to 75 Compounds of the formula 1.3 in which R^14b is as defined in any of tables 1 to 25 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 76 to 100

Compounds of the formula 1.4 in which R^14b is as defined in any of tables 1 to 25 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 101 to 125

Compounds of the formula 1.5 in which R^14b is as defined in any of tables 1 to 25 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 126

Compounds of the formula 1.6 in which R^9a and R^9b are methyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 127

Compounds of the formula 1.6 in which R^9a and R^9b are ethyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 128

Compounds of the formula 1.6 in which R^9a and R^9b are n-propyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 129

Compounds of the formula 1.6 in which R^9a and R^9b are isopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 130

Compounds of the formula 1.6 in which R^9a and R^9b are n-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 131

Compounds of the formula 1.6 in which R^9a and R^9b are sec-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 132

Compounds of the formula 1.6 in which R^9a and R^9b are isobutyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 133

Compounds of the formula 1.6 in which R^9a and R^9b are tert-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 134

Compounds of the formula 1.6 in which R^9a and R^9b are cyclopropyl and the

combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 135

Compounds of the formula 1.6 in which R^9a and R^9b are -Chb-cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 136

Compounds of the formula 1.6 in which R^9a and R^9b are allyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 137

Compounds of the formula 1.6 in which R^9a and R^9b are propargyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 138

Compounds of the formula 1.6 in which R^9a is hydrogen, R^9b is methyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 139

Compounds of the formula 1.6 in which R^9a is hydrogen, R^9b is ethyl and the

Table 140

Compounds of the formula 1.6 in which R^9a is hydrogen, R^9b is n-propyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 141

Compounds of the formula 1.6 in which R^9a is hydrogen, R^9b is isopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 142

Compounds of the formula 1.6 in which R^9a is hydrogen, R^9b is n-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 143

Compounds of the formula 1.6 in which R^9a is hydrogen, R^9b is sec-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 144

Compounds of the formula 1.6 in which R^9a is hydrogen, R^9b is isobutyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 145 Compounds of the formula 1.6 in which R^9a is hydrogen, R^9b is tert-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 146

Compounds of the formula 1.6 in which R^9a is hydrogen, R^9b is cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 147

Compounds of the formula 1.6 in which R^9a is hydrogen, R^9b is -Chb-cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 148

Compounds of the formula 1.6 in which R^9a is methyl, R^9b is ethyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 149

Compounds of the formula 1.6 in which R^9a is methyl, R^9b is n-propyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 150

Compounds of the formula 1.6 in which R^9a is methyl, R^9b is isopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 151

Compounds of the formula 1.6 in which R^9a is methyl, R^9b is n-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 152

Compounds of the formula 1.6 in which R^9a is methyl, R^9b is sec-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 152

Compounds of the formula 1.6 in which R^9a is methyl, R^9b is isobutyl and the

Table 154

Compounds of the formula 1.6 in which R^9a is methyl, R^9b is tert-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 155 Compounds of the formula 1.6 in which R^9a is methyl, R^9b is cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 156

Compounds of the formula 1.6 in which R^9a is methyl, R^9b is -Chb-cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 157

Compounds of the formula 1.6 in which R^9a is ethyl, R^9b is n-propyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 158

Compounds of the formula 1.6 in which R^9a is ethyl, R^9b is isopropyl and the

Table 159

Compounds of the formula 1.6 in which R^9a is ethyl, R^9b is n-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 160

Compounds of the formula 1.6 in which R^9a is ethyl, R^9b is sec-butyl and the

Table 161

Compounds of the formula 1.6 in which R^9a is ethyl, R^9b is isobutyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 162

Compounds of the formula 1.6 in which R^9a is ethyl, R^9b is tert-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 163

Compounds of the formula 1.6 in which R^9a is ethyl, R^9b is cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 164

Compounds of the formula 1.6 in which R^9a is ethyl, R^9b is -Chb-cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 165

Compounds of the formula 1.6 in which R^9a is n-propyl, R^9b is isopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 166

Compounds of the formula 1.6 in which R^9a is n-propyl, R^9b is n-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 167

Compounds of the formula 1.6 in which R^9a is n-propyl, R^9b is sec-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 168

Compounds of the formula 1.6 in which R^9a is n-propyl, R^9b is isobutyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 169

Compounds of the formula 1.6 in which R^9a is n-propyl, R^9b is tert-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 170

Compounds of the formula 1.6 in which R^9a is n-propyl, R^9b is cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 171

Compounds of the formula 1.6 in which R^9a is n-propyl, R^9b is -Chb-cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 172

Compounds of the formula 1.6 in which R^9a is isopropyl, R^9b is n-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 173

Compounds of the formula 1.6 in which R^9a is isopropyl, R^9b is sec-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 174

Compounds of the formula 1.6 in which R^9a is isopropyl, R^9b is isobutyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 175 Compounds of the formula 1.6 in which R^9a is isopropyl, R^9b is tert-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 176

Compounds of the formula 1.6 in which R^9a is isopropyl, R^9b is cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 177

Compounds of the formula 1.6 in which R^9a is isopropyl, R^9b is -Chb-cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 178

Compounds of the formula 1.6 in which R^9a is n-butyl, R^9b is sec-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 179

Compounds of the formula 1.6 in which R^9a is n-butyl, R^9b is isobutyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 180

Compounds of the formula 1.6 in which R^9a is n-butyl, R^9b is tert-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 181

Compounds of the formula 1.6 in which R^9a is n-butyl, R^9b is cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 182

Compounds of the formula 1.6 in which R^9a is n-butyl, R^9b is -Chb-cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 183

Compounds of the formula 1.6 in which R^9a is sec-butyl, R^9b is isobutyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 184

Compounds of the formula 1.6 in which R^9a is sec-butyl, R^9b is tert-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 185

Compounds of the formula 1.6 in which R^9a is sec-butyl, R^9b is cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 186

Compounds of the formula 1.6 in which R^9a is sec-butyl, R^9b is -Chb-cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 187

Compounds of the formula 1.6 in which R^9a is isobutyl, R^9b is tert-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 188

Compounds of the formula 1.6 in which R^9a is isobutyl, R^9b is cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 189

Compounds of the formula 1.6 in which R^9a is isobutyl, R^9b is -Chb-cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 198

Compounds of the formula 1.6 in which R^9a is tert-butyl, R^9b is cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 191

Compounds of the formula 1.6 in which R^9a is tert-butyl, R^9b is -Chb-cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 192

Compounds of the formula 1.6 in which R^9a is cyclopropyl, R^9b is -Chb-cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 193

Compounds of the formula 1.6 in which R^9a and R^9b together form a bridging group -(CH2)4- and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 194 Compounds of the formula 1.6 in which R^9a and R^9b together form a bridging group -CH2-S-CH2-CH2- and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 195

Compounds of the formula 1.6 in which R^9a and R^9b together form a bridging group -(CH2)5- and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 196

Compounds of the formula 1.6 in which R^9a and R^9b together form a bridging group -CH2-CH2-O-CH2-CH2- and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 197 to 267

Compounds of the formula 1.7 in which the combination of R^9a and R^9b is as defined in any of tables 126 to 196 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 268 to 338

Compounds of the formula 1.8 in which the combination of R^9a and R^9b is as defined in any of tables 126 to 196 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 339 to 409

Compounds of the formula 1.9 in which the combination of R^9a and R^9b is as defined in any of tables 126 to 196 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 410 to 480

Compounds of the formula 1.10 in which the combination of R^9a and R^9b is as defined in any of tables 126 to 196 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 481

Compounds of the formula 1.10 in which R^9a and R^9b together form a bridging group -NH-CH₂CH₂-S-and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 482

Compounds of the formula 1.10 in which R^9a and R^9b together form a bridging group -N(CH3)-CH₂CH2-S-and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 483

Compounds of the formula 1.10 in which R^9a and R^9b together form a bridging group -NH-CH₂CH₂-S(0)-and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 484

Compounds of the formula 1.10 in which R^9a and R^9b together form a bridging group -N(CH3)-CH₂CH2-S(0)-and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 485

Compounds of the formula 1.1 1 in which R^10a is hydrogen, R^10b is hydrogen and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 486

Compounds of the formula 1.1 1 in which R^10a is methyl, R^10b is methyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 487

Compounds of the formula 1.1 1 in which R^10a is ethyl, R^10b is ethyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 488

Compounds of the formula 1.1 1 in which R^10a is isopropyl, R^10b is isopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 489

Compounds of the formula 1.1 1 in which R^10a is hydrogen, R^10b is methyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 490

Compounds of the formula 1.1 1 in which R^10a is hydrogen, R^10b is ethyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 491

Compounds of the formula 1.1 1 in which R^10a is hydrogen, R^10b is isopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 492

Compounds of the formula 1.1 1 in which R^10a is methyl, R^10b is ethyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 493

Compounds of the formula 1.1 1 in which R^10a is methyl, R^10b is isopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 494

Compounds of the formula 1.1 1 in which R^10a is ethyl, R^10b is isopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 495 to 504

Compounds of the formula 1.12 in which the combination of R^10a and R^10b is as defined in any of tables 485 to 494 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 505

Compounds of the formula 1.13 in which the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 506

Compounds of the formula 1.14 in which the combination of R^2a, R² , R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 507

Compounds of the formula 1.15 in which the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 508

Compounds of the formula 1.16 in which the combination of R^2a, R² , R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 509

Compounds of the formula 1.17 in which the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 510

Compounds of the formula 1.18 in which the combination of R^2a, R² , R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 51 1

Compounds of the formula 1.19 in which the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 512

Compounds of the formula I.20 in which the combination of R^2a, R² , R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 513

Compounds of the formula 1.21 in which the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 514

Compounds of the formula 1.22 in which the combination of R^2a, R² , R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 515 Compounds of the formula 1.23 in which the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 516

Compounds of the formula 1.24 in which the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 517

Compounds of the formula 1.25 in which the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 518

Compounds of the formula 1.26 in which the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 519

Compounds of the formula 1.27 in which the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 520

Compounds of the formula 1.28 in which the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 521

Compounds of the formula 1.29 in which the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 522

Compounds of the formula 1.30 in which the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 523

Compounds of the formula 1.31 in which the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 524

Compounds of the formula 1.32 in which the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 525

Compounds of the formula 1.33 in which R⁸ is hydrogen, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 526

Compounds of the formula 1.33 in which R⁸ is methyl, and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 527

Compounds of the formula 1.33 in which R⁸ is ethyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 528 Compounds of the formula 1.33 in which R⁸ is propyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 529

Compounds of the formula 1.33 in which R⁸ is isopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 530

Compounds of the formula 1.33 in which R⁸ is sec-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 531

Compounds of the formula 1.33 in which R⁸ is isobutyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 532

Compounds of the formula 1.33 in which R⁸ is tert-butyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 533

Compounds of the formula 1.33 in which R⁸ is CF3 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 534

Compounds of the formula 1.33 in which R⁸ is CH2CHF2 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 535

Compounds of the formula 1.33 in which R⁸ is CH2CF3 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 536

Compounds of the formula 1.33 in which R⁸ is CH2CH2CF3 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 537

Compounds of the formula 1.33 in which R⁸ is cyclopropyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 538

Compounds of the formula 1.33 in which R⁸ is methylthiomethyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 539

Compounds of the formula 1.33 in which R⁸ is ethylthiomethyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 540

Compounds of the formula 1.33 in which R⁸ is methylsulfinylmethyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 541 Compounds of the formula 1.33 in which R⁸ is ethylsulfinylmethyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 532

Compounds of the formula 1.33 in which R⁸ is methylsulfonylmethyl and the

Table 543

Compounds of the formula 1.33 in which R⁸ is ethylsulfonylmethyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 544

Compounds of the formula 1.33 in which R⁸ is phenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 545

Compounds of the formula 1.33 in which R⁸ is 2-fluorophenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 546

Compounds of the formula 1.33 in which R⁸ is 3-fluorophenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 547

Compounds of the formula 1.33 in which R⁸ is 4-fluorophenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 548

Compounds of the formula 1.33 in which R⁸ is 2,3-difluorophenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 549

Compounds of the formula 1.33 in which R⁸ is 2,4-difluorophenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 550

Compounds of the formula 1.33 in which R⁸ is 2,5-difluorophenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 551

Compounds of the formula 1.33 in which R⁸ is 2,6-difluorophenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 552

Compounds of the formula 1.33 in which R⁸ is 3,4-difluorophenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 553

Compounds of the formula 1.33 in which R⁸ is 3,5-difluorophenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 554

Compounds of the formula 1.33 in which R⁸ is 2-chlorophenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 555

Compounds of the formula 1.33 in which R⁸ is 3-chlorophenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 556

Compounds of the formula 1.33 in which R⁸ is 4-chlorophenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 557

Compounds of the formula 1.33 in which R⁸ is 2-methoxyphenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 558

Compounds of the formula 1.33 in which R⁸ is 3-methoxyphenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 559

Compounds of the formula 1.33 in which R⁸ is 4-methoxyphenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 560

Compounds of the formula 1.33 in which R⁸ is thietan-3-yl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 561

Compounds of the formula 1.33 in which R⁸ is 1 -oxo-thietan-3-yl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 562

Compounds of the formula 1.33 in which R⁸ is 1 ,1 -dioxo-thietan-3-yl and the

Table 563

Compounds of the formula 1.33 in which R⁸ is pyridin-2-yl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 564

Compounds of the formula 1.33 in which R⁸ is pyridin-3-yl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 565

Compounds of the formula 1.33 in which R⁸ is pyridin-4-yl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 566 Compounds of the formula 1.33 in which R⁸ is 4-chloropyridin-3-yl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 567

Compounds of the formula 1.33 in which R⁸ is -NH-CH3 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Table 568

Compounds of the formula 1.33 in which R⁸ is -NH-CH2CH3 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 569

Compounds of the formula 1.33 in which R⁸ is -NH-CH2CH2CH3 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 570

Compounds of the formula 1.33 in which R⁸ is -NH-CH2CN and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 571

Compounds of the formula 1.33 in which R⁸ is -NH-CH2CHF2 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 572

Compounds of the formula 1.33 in which R⁸ is -NH-CH2CF3 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 573

Compounds of the formula 1.33 in which R⁸ is -NH-phenyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table 574

Compounds of the formula 1.33 in which R⁸ is -NH-benzyl and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Tables 575 to 624

Compounds of the formula 1.34 in which R⁸ is as defined in any of tables 525 to 574 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 625 to 674

Compounds of the formula 1.35 in which R⁸ is as defined in any of tables 525 to 574 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 675 to 724

Compounds of the formula 1.36 in which R⁸ is as defined in any of tables 525 to 574 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 725 to 795 Compounds of the formula 1.37 in which R^10a is hydrogen, the combination of R^9a and R^9b is as defined in any of tables 126 to 196 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 796 to 866

Compounds of the formula 1.37 in which R^10a is methyl, the combination of R^9a and R^9b is as defined in any of tables 126 to 196 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 867 to 937

Compounds of the formula 1.37 in which R^10a is ethyl, the combination of R^9a and R^9b is as defined in any of tables 126 to 196 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 938 to 1008

Compounds of the formula 1.37 in which R^10a is propyl, the combination of R^9a and R^9b is as defined in any of tables 126 to 196 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 1009 to 1079

Compounds of the formula 1.37 in which R^10a is isopropyl, the combination of R^9a and R^9b is as defined in any of tables 126 to 196 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 1080 to 1434

Compounds of the formula 1.38 in which the combination of R^9a, R^9b and R^10a is as defined in any of tables 725 to 1079 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 1435 to 1454

Compounds of the formula 1.39 in which R¹⁴ is as defined in any of tables 1 to 20 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 1455 to 1474

Compounds of the formula 1.40 in which R¹⁴ is as defined in any of tables 1 to 20 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 1475 to 1545

Compounds of the formula 1.41 in which the combination of R^9a and R⁹ is as defined in any of tables 126 to 196 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A

Tables 1546 to 1616

Compounds of the formula 1.42 in which the combination of R^9a and R⁹ is as defined in any of tables 126 to 196 and the combination of R^2a, R^2b, R^2c and R⁴ for a compound corresponds in each case to one row of Table A Table A

No. _R2a _R2b _R2c R⁴

A-1 F H F H

A-2 F F F H

A-3 F CI F H

A-4 F Br F H

A-5 F H CI H

A-6 F H Br H

A-7 CI H CI H

A-8 CI CI CI H

A-9 CI F CI H

A-10 CI Br CI H

A-1 1 CI H Br H

A-12 Br H Br H

A-13 Br F Br H

A-14 Br CI Br H

A-15 CF₃ H F H

A-16 CF₃ H CI H

A-17 CF₃ H Br H

A-18 CF₃ H CF₃ H

A-19 CF₃ F F H

A-20 CF₃ CI CI H

A-21 CF₃ Br Br H

A-22 H H F H

A-23 H H CI H

A-24 H H Br H

A-25 H H CF₃ H

A-26 F H F CHs

A-27 F F F CHs

A-28 F CI F CHs

A-29 F Br F CHs

A-30 F H CI CHs

A-31 F H Br CHs

A-32 CI H CI CHs

A-33 CI CI CI CHs

A-34 CI F CI CHs

_R2a _R2b _R2c R⁴

A-109 CI F CI CHF₂

A-1 10 CI Br CI CHF₂

A-1 1 1 CI H Br CHF₂

A-1 12 Br H Br CHF₂

A-1 13 Br F Br CHF₂

A-1 14 Br CI Br CHF₂

A-1 15 CFs H F CHF₂

A-1 16 CFs H CI CHF₂

A-1 17 CFs H Br CHF₂

A-1 18 CFs H CFs CHF₂

A-1 19 CFs F F CHF₂

A-120 CFs CI CI CHF₂

A-121 CFs Br Br CHF₂

A-122 H H F CHF₂

A-123 H H CI CHF₂

A-124 H H Br CHF₂

A-125 H H CFs CHF₂

A-126 F H F CFs

A-127 F F F CFs

A-128 F CI F CFs

A-129 F Br F CFs

A-130 F H CI CFs

A-131 F H Br CFs

A-132 CI H CI CFs

A-133 CI CI CI CFs

A-134 CI F CI CFs

A-135 CI Br CI CFs

A-136 CI H Br CFs

A-137 Br H Br CFs

A-138 Br F Br CFs

A-139 Br CI Br CFs

A-140 CFs H F CFs

A-141 CFs H CI CFs

A-142 CFs H Br CFs

A-143 CFs H CFs CFs

A-144 CFs F F CFs

A-145 CFs CI CI CFs

/.t£6£0/£lOZd3/I3d εε9.9ΐ/ειοζ OAV

/.t£6£0/£lOZd3/I3d εε9.9ΐ/ειοζ OAV _R2a _R2b _R2c R⁴

A-220 CFs CI CI C≡CH

A-221 CFs Br Br C≡CH

A-222 H H F C≡CH

A-223 H H CI C≡CH

A-224 H H Br C≡CH

A-225 H H CFs C≡CH

A-226 F H F ^cCsH₅ ^*

A-227 F F F ^cCsH₅ ^*

A-228 F CI F ^cCsH₅ ^*

A-229 F Br F ^cCsH₅ ^*

A-230 F H CI ^cCsH₅ ^*

A-231 F H Br ^cCsH₅ ^*

A-232 CI H CI ^cCsH₅ ^*

A-233 CI CI CI ^cCsH₅ ^*

A-234 CI F CI ^cCsH₅ ^*

A-235 CI Br CI ^cCsH₅ ^*

A-236 CI H Br ^cCsH₅ ^*

A-237 Br H Br ^cCsH₅ ^*

A-238 Br F Br ^cCsH₅ ^*

A-239 Br CI Br ^cCsH₅ ^*

A-240 CFs H F ^cCsH₅ ^*

A-241 CFs H CI ^cCsH₅ ^*

A-242 CFs H Br ^cCsH₅ ^*

A-243 CFs H CFs ^cCsH₅ ^*

A-244 CFs F F ^cCsH₅ ^*

A-245 CFs CI CI ^cCsH₅ ^*

A-246 CFs Br Br ^cCsH₅ ^*

A-247 H H F ^cCsH₅ ^*

A-248 H H CI ^cCsH₅ ^*

A-249 H H Br ^cCsH₅ ^*

A-250 H H CFs ^cCsH₅ ^*

A-251 F H F F

A-252 F F F F

A-253 F CI F F

A-254 F Br F F

A-255 F H CI F

A-256 F H Br F _R2a _R2b _R2c R⁴

A-257 CI H CI F

A-258 CI CI CI F

A-259 CI F CI F

A-260 CI Br CI F

A-261 CI H Br F

A-262 Br H Br F

A-263 Br F Br F

A-264 Br CI Br F

A-265 CFs H F F

A-266 CFs H CI F

A-267 CFs H Br F

A-268 CFs H CFs F

A-269 CFs F F F

A-270 CFs CI CI F

A-271 CFs Br Br F

A-272 H H F F

A-273 H H CI F

A-274 H H Br F

A-275 H H CFs F

A-276 F H F CI

A-277 F F F CI

A-278 F CI F CI

A-279 F Br F CI

A-280 F H CI CI

A-281 F H Br CI

A-282 CI H CI CI

A-283 CI CI CI CI

A-284 CI F CI CI

A-285 CI Br CI CI

A-286 CI H Br CI

A-287 Br H Br CI

A-288 Br F Br CI

A-289 Br CI Br CI

A-290 CFs H F CI

A-291 CFs H CI CI

A-292 CFs H Br CI

A-293 CFs H CFs CI _R2a _R2b _R2c R⁴

A-294 CFs F F CI

A-295 CFs CI CI CI

A-296 CFs Br Br CI

A-297 H H F CI

A-298 H H CI CI

A-299 H H Br CI

A-300 H H CFs CI

A-301 F H F Br

A-302 F F F Br

A-303 F CI F Br

A-304 F Br F Br

A-305 F H CI Br

A-306 F H Br Br

A-307 CI H CI Br

A-308 CI CI CI Br

A-309 CI F CI Br

A-310 CI Br CI Br

A-31 1 CI H Br Br

A-312 Br H Br Br

A-313 Br F Br Br

A-314 Br CI Br Br

A-315 CFs H F Br

A-316 CFs H CI Br

A-317 CFs H Br Br

A-318 CFs H CFs Br

A-319 CFs F F Br

A-320 CFs CI CI Br

A-321 CFs Br Br Br

A-322 H H F Br

A-323 H H CI Br

A-324 H H Br Br

A-325 H H CFs Br

A-326 F H F CN

A-327 F F F CN

A-328 F CI F CN

A-329 F Br F CN

A-330 F H CI CN _R2a _R2b _R2c R⁴

A-331 F H Br CN

A-332 CI H CI CN

A-333 CI CI CI CN

A-334 CI F CI CN

A-335 CI Br CI CN

A-336 CI H Br CN

A-337 Br H Br CN

A-338 Br F Br CN

A-339 Br CI Br CN

A-340 CFs H F CN

A-341 CFs H CI CN

A-342 CFs H Br CN

A-343 CFs H CFs CN

A-344 CFs F F CN

A-345 CFs CI CI CN

A-346 CFs Br Br CN

A-347 H H F CN

A-348 H H CI CN

A-349 H H Br CN

A-350 H H CFs CN

A-351 F H F OCHs

A-352 F F F OCHs

A-353 F CI F OCHs

A-354 F Br F OCHs

A-355 F H CI OCHs

A-356 F H Br OCHs

A-357 CI H CI OCHs

A-358 CI CI CI OCHs

A-359 CI F CI OCHs

A-360 CI Br CI OCHs

A-361 CI H Br OCHs

A-362 Br H Br OCHs

A-363 Br F Br OCHs

A-364 Br CI Br OCHs

A-365 CFs H F OCHs

A-366 CFs H CI OCHs

A-367 CFs H Br OCHs

_R2a _R2b _R2c R⁴

A-405 F H CI OCH(CHs)₂

A-406 F H Br OCH(CHs)₂

A-407 CI H CI OCH(CHs)₂

A-408 CI CI CI OCH(CHs)₂

A-409 CI F CI OCH(CHs)₂

A-410 CI Br CI OCH(CHs)₂

A-41 1 CI H Br OCH(CHs)₂

A-412 Br H Br OCH(CHs)₂

A-413 Br F Br OCH(CHs)₂

A-414 Br CI Br OCH(CHs)₂

A-415 CFs H F OCH(CHs)₂

A-416 CFs H CI OCH(CHs)₂

A-417 CFs H Br OCH(CHs)₂

A-418 CFs H CFs OCH(CHs)₂

A-419 CFs F F OCH(CHs)₂

A-420 CFs CI CI OCH(CHs)₂

A-421 CFs Br Br OCH(CHs)₂

A-422 H H F OCH(CHs)₂

A-423 H H CI OCH(CHs)₂

A-424 H H Br OCH(CHs)₂

A-425 H H CFs OCH(CHs)₂

A-426 F H F OCH₂CH=CH₂

A-427 F F F OCH₂CH=CH₂

A-428 F CI F OCH₂CH=CH₂

A-429 F Br F OCH₂CH=CH₂

A-430 F H CI OCH₂CH=CH₂

A-431 F H Br OCH₂CH=CH₂

A-432 CI H CI OCH₂CH=CH₂

A-433 CI CI CI OCH₂CH=CH₂

A-434 CI F CI OCH₂CH=CH₂

A-435 CI Br CI OCH₂CH=CH₂

A-436 CI H Br OCH₂CH=CH₂

A-437 Br H Br OCH₂CH=CH₂

A-438 Br F Br OCH₂CH=CH₂

A-439 Br CI Br OCH₂CH=CH₂

A-440 CFs H F OCH₂CH=CH₂

A-441 CFs H CI OCH₂CH=CH₂

_R2a _R2b _R2c R⁴

A-627 F F F SCH₂CH=CH₂

A-628 F CI F SCH₂CH=CH₂

A-629 F Br F SCH₂CH=CH₂

A-630 F H CI SCH₂CH=CH₂

A-631 F H Br SCH₂CH=CH₂

A-632 CI H CI SCH₂CH=CH₂

A-633 CI CI CI SCH₂CH=CH₂

A-634 CI F CI SCH₂CH=CH₂

A-635 CI Br CI SCH₂CH=CH₂

A-636 CI H Br SCH₂CH=CH₂

A-637 Br H Br SCH₂CH=CH₂

A-638 Br F Br SCH₂CH=CH₂

A-639 Br CI Br SCH₂CH=CH₂

A-640 CFs H F SCH₂CH=CH₂

A-641 CFs H CI SCH₂CH=CH₂

A-642 CFs H Br SCH₂CH=CH₂

A-643 CFs H CFs SCH₂CH=CH₂

A-644 CFs F F SCH₂CH=CH₂

A-645 CFs CI CI SCH₂CH=CH₂

A-646 CFs Br Br SCH₂CH=CH₂

A-647 H H F SCH₂CH=CH₂

A-648 H H CI SCH₂CH=CH₂

A-649 H H Br SCH₂CH=CH₂

A-650 H H CFs SCH₂CH=CH₂

A-651 F H F SCHF₂

A-652 F F F SCHF₂

A-653 F CI F SCHF₂

A-654 F Br F SCHF₂

A-655 F H CI SCHF₂

A-656 F H Br SCHF₂

A-657 CI H CI SCHF₂

A-658 CI CI CI SCHF₂

A-659 CI F CI SCHF₂

A-660 CI Br CI SCHF₂

A-661 CI H Br SCHF₂

A-662 Br H Br SCHF₂

A-663 Br F Br SCHF₂ _R2a _R2b _R2c R⁴

A-664 Br CI Br SCHF₂

A-665 CFs H F SCHF₂

A-666 CFs H CI SCHF₂

A-667 CFs H Br SCHF₂

A-668 CFs H CFs SCHF₂

A-669 CFs F F SCHF₂

A-670 CFs CI CI SCHF₂

A-671 CFs Br Br SCHF₂

A-672 H H F SCHF₂

A-673 H H CI SCHF₂

A-674 H H Br SCHF₂

A-675 H H CFs SCHF₂

A-676 F H F SCH(CHs)₂

A-677 F F F SCH(CHs)₂

A-678 F CI F SCH(CHs)₂

A-679 F Br F SCH(CHs)₂

A-680 F H CI SCH(CHs)₂

A-681 F H Br SCH(CHs)₂

A-682 CI H CI SCH(CHs)₂

A-683 CI CI CI SCH(CHs)₂

A-684 CI F CI SCH(CHs)₂

A-685 CI Br CI SCH(CHs)₂

A-686 CI H Br SCH(CHs)₂

A-687 Br H Br SCH(CHs)₂

A-688 Br F Br SCH(CHs)₂

A-689 Br CI Br SCH(CHs)₂

A-690 CFs H F SCH(CHs)₂

A-691 CFs H CI SCH(CHs)₂

A-692 CFs H Br SCH(CHs)₂

A-693 CFs H CFs SCH(CHs)₂

A-694 CFs F F SCH(CHs)₂

A-695 CFs CI CI SCH(CHs)₂

A-696 CFs Br Br SCH(CHs)₂

A-697 H H F SCH(CHs)₂

A-698 H H CI SCH(CHs)₂

A-699 H H Br SCH(CHs)₂

A-700 H H CFs SCH(CHs)₂

* ^CC3H₅ = cyclopropyl

Among the above compounds, preference is given to compounds 1.1 , 1.5, 1.6, 1.9 to 1.18, 1.21 to I.25, I.27 to I.30, I.33, I.36 and 1.39 to I.42. More preference is given to compounds 1.1 , I.5, I.6, I.9 to 1.16, 1.21 to 1.25, I.27 to I.29, I.36, I.40 and I.42.

The compounds of the formula (I) can be prepared by standard methods of organic chemistry, e.g. by the methods described hereinafter or in the synthesis descriptions of the working examples. The substituents, variables and indices are as defined above for formula (I), if not otherwise specified. The compounds (I) can be prepared by coupling a compound 2 with a compound 3, wherein the "G-ring" carries a group A or a precursor A' of A, and LG is a halide ion, preferably a chloride, bromide or iodide ion, for instance under the conditions of a Heck reaction via Pd-catalyzed cross coupling, generally in the presence of a base, as shown in scheme 1 . A typical catalyst is tetrakis(triphenylphosphine)palladium(0). Solvents such as tetrahydrofuran, acetonitrile, diethyl ether and dioxane are suitable. Other methods for introduction of the "G-ring" are the Suzuki, Stille and Kumada coupling procedures; see for example Tetrahedron, 2004, 60, 8991 -9016. If A' is a precursor of A, this can be then converted into the final group A.

Sche

The compound 2 wherein Z is O can for example be prepared by an amidation reaction of the acrylic acid (derivative) 5 with the benzylic amine 4 as shown in scheme 2. LG is OH, CI, Br, an anhydride residue (-O-C(O)-R) or an active ester residue (-OR').

-0-C(0)-R is a group which can be displaced easily by the amino group of 4. Suitable acid derivatives with which the carboxylic acid 5 (LG = OH) can form suitable mixed anhydrides are, for example, the esters of chloroformic acid, for example isopropyl chloroformate and isobutyl chloroformate, or of chloroacetic acid. If 5 with LG = OR' forms a so-called active ester, this is obtained in a formal sense by the reaction of the acid 5 (LG = OH) with an active ester-forming alcohol, such as p-nitrophenol,

N-hydroxybenzotriazole (HOBt), N-hydroxysuccinimide or OPfp (pentafluorophenol). In case that LG is OH, amidation is preferably carried out by first activating the carboxylic acid with oxalylchloride [(COCI)2] or thionylchloride (SOC ) to the respective acid chlorides, followed by reaction with amine 4. Alternatively, amidation is carried out in the presence of a coupling reagent. Suitable coupling reagents (activators) are well known and are for instance selected from carbodiimides, such as DCC

(dicyclohexylcarbodiimide) and DIPC (diisopropylcarbodiimide), benzotriazol derivatives, such as HATU (0-(7-azabenzotriazol-1 -yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate), HBTU ((0-benzotriazol-1 -yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate) and HCTU (1 H-benzotriazolium-1 -[bis(dimethylamino)- methylene]-5-chloro tetrafluoroborate) and phosphonium-derived activators, such as BOP ((benzotriazol-1 -yloxy)-tris(dimethylamino)phosphonium hexafluorophosphate), Py-BOP ((benzotriazol-1 -yloxy)-tripyrrolidinphosphonium hexafluorophosphate) and Py-BrOP (bromotripyrrolidinphosphonium hexafluorophosphate). Generally, the activator is used in excess. The benzotriazol and phosphonium coupling reagents generally used in a basic medium.

Scheme

The benzylic amine 4^a, wherein L is H, can be prepared by reaction the aldehyde or ketone 7 with hydroxylamine to the oxime 6, as shown in scheme 3. Subsequent reduction and, in case that R³ is not hydrogen, reaction with a group X-R³, wherein X a leaving group, such as a halogen atom, and R³ is not H, yields compound 4^a.

Scheme 3

Alternatively, the benzylic amine 4 can be prepared by reaction the aldehyde or ketone 7 with an amine NH2R³ to the imine 8, as shown in scheme 4. Standard reduction (hydrogenation) conditions give a compound 4^a, wherein L is H. For obtaining compounds 4 wherein L is a C-bound radical, such as alkyl, cycloalkyi, alkenyl, alkynyl, phenyl or a C-bound heterocyclyl, the imine 8 is reacted with a Grignard reagent L-MgX, wherein X is CI, Br or I, or with a lithium organic compound L-Li.

Scheme 4

The benzylic amine 4^b, wherein L is OH, can be prepared as shown in scheme 5 by reacting the imine 8 with a carbonic dichloride COC in the presence of a base, such as Hunig's base (Ν,Ν-diisopropylethylamine) and subsequent quenching with an aqueous solution, as described in WO 2004/0131 10. Reaction of 4^b with SOC in the presence of a base, such as triethylamine, yields an amine 4° wherein L is CI.

Scheme 5

The benzylic amine 4^d, wherein L is alkoxy, can be prepared as shown in scheme 6 in analogy to the reactions described in J. Org. Chem 1988, 53(4), 3358-3361 , Zhurnal Organicheskoi Khimii 1981 , 17(7), 1420-1429, 1263-1271 , J. Org. Chem. USSR (English Translation) 1992, 28(19.1 ), 1635-1643 or Zhurnal Organicheskoi Khimii 1992, 28(10), 2042-2053 by reacting the acyl chloride 9 (R = alkyl) with sodium azide to 10. Curtius rearrangement yields the isocyanate 11 . This is reacted with an alcohol R'OH (R' = Ci-C4-alkyl or benzyl) to the carbamate 12, which is the hydrolysed to 4^d.

Alternatively, isocyanate 11 can be reacted with water and thereby directly converted into the amine 4^d.

Scheme 6

Amines 4^e, wherein L is CN, can be prepared in analogy to the reaction described in Tetrahedron 1993, 49(8), 1541 -1546 by reacting the amide 13 with phosphorus pentachloride to the nitrile 14. Grignard reaction with 15 yields the imine 16, which is then reacted with HCN to 4^e. as shown in scheme 7.

Scheme 7

Amines 4^f, wherein L is NH2, can be prepared in analogy to the reaction described in Chemistry of heterocyclic compounds 2004, 40(3), 370-376 by reacting the imine 17 with and amine NH2R³ to 18, as shown in scheme 8. Hydrolysis of the carbamate group yields 4^f.

Scheme 8

Compounds 49, wherein L and R² form a ring, can be prepared in analogy to the synthesis described in EP-A-2042480 by reacting 19 with a Grignard or lithium organyl M-R¹, wherein M is Li or MgCI, to 20. Reaction with sodium azide in the presence of an acid, such as trifluoroacetic acid, yields 21 , which is then reduced to 49, as shown in scheme 9.

Compounds of formula I wherein Z is O can alternatively be prepared in an amidation reaction of the acrylic acid (derivative) 22 with the benzylic amine 4, as shown in scheme 10. LG is like above OH, CI, Br, an anhydride residue (-O-C(O)-R) or an active ester residue (-OR'). Suitable amidation conditions correspond to those described above for scheme 2.

Scheme 10

The acrylic acid (derivative) 22 can be prepared by reacting the acrylic acid (derivative) 23 with a heterocyclic compound 3 to compound 24 as shown in scheme 11 , under the conditions of a Heck coupling reaction, as described above for scheme 1 . PG in structures 23 and 24 stands for a protecting group and is for example Ci-C4-alkyl or benzyl. Ester compound 24 can be hydrolized to the corresponding acid (compound 22, wherein LG = OH) and the acid can be converted into a compound 22, wherein LG is CI, Br, an anhydride residue (-O-C(O)-R) or an active ester residue (-OR') by standard reaction conditions.

Scheme 1 1

23 24 22

Compounds wherein Z is S can be prepared by reacting a compound I, Γ or 2 with Lawesson's reagent or P2S5.

Compounds wherein E and R⁴ or E and R^4a or two radicals R⁴ or R⁴ and R^4a or R⁴ and R⁵ or R^4a and R⁵, together with the atoms to which they are bound, form a ring, can be prepared by using the respective starting material. This is either commercially available or can be prepared in analogy to known methods, such as described, for example, in WO 02/36583, WO 02/59099, WO 2005/034880, WO 2007/146758 or

WO 201 1/012538.

A' as a precursor of A is typically an ester group -CO2R' wherein R' is typically C1-C4- alkyl, such as methyl or tert-butyl, a halogen atom, CN, carboxy, tert-butoxycarbonyl, 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 radicals selected from Ci-C4-alkyl, Ci-C4-haloalkyl Ci-C4-alkoxy or Ci-C4-haloalkoxy. A' as a precursor of A is preferably an ester group -CO2R', a halogen atom or -OS02-R^z1, where R' and R^z1 are as defined above, and is more preferably an ester group -CO2R' or a halogen atom.

Compounds Γ, in which A' is a precursor of A, can be converted as shown below into the different groups A¹ to A⁵. Compounds Γ, in which A is CI, Br, I or -OS02-R^z1, where R^z1 is as defined above, can be converted to compounds I wherein A is a group A¹, wherein A¹ is an imino group -C(=NR⁷)R⁸, by reaction with carbon monoxide and a hydride source, such as triethylsilane, in the presence of a transition metal complex catalyst, preferably a palladium catalyst, to a carbonyl compound II. This reaction converts the starting group A' into a carbonyl group -C(=0)H.

Of course, in compound II, neither of G² or G³ is C-A.

The aldehyde II can also be obtained by reducing the methyl ester XI (see below; R methyl) with diisobutylaluminium hydride (DIBAL-H) either directly to the aldehyde II via the corresponding alcohol, which is then oxidized to the aldehyde.

For obtaining compounds in which R⁸ in the imino group is H, such carbonyl compounds II are then reacted with an amine (derivative) NH2R⁷. Alternatively, the compound Γ, in which A is CI, Br, I or -OS02-R^z1, where R^z1 is as defined above, can be reacted in a one pot reaction with carbon monoxide and hydrogen in the presence of a transition metal complex catalyst and the amine NH2R⁷.

For obtaining compounds in which R⁸ in the imino group is not H, the carbonyl compounds are reacted with a Grignard reagent R⁸-MgHal, where Hal is CI, Br or I, or an organolithium compound R⁸-Li to obtain an alcohol of formula III

This is then reacted with an amine NH2R⁷ to the respective imine compound.

These reactions can be carried out in analogy to the methods described in

PCT/EP 201 1/060388 or in WO 2010/072781 and the references cited therein, especially WO 2006135763, Fattorusso et al, J. Med. Chem. 2008, 51 , 1333-1343 and WO 2008/122375.

Of course, in compounds III and IV, neither of G² or G³ is C-A. Compounds I wherein A is a group A¹, wherein A¹ is -C(=NOR⁹)N(R^10a)R^10c can be prepared in analogy to the method described in WO 2010/072602 by reacting an aldehyde V with hydroxylamine to the oxime VI. This is then reacted with

N-chlorosuccinimide (NCS), followed by an amine NH(R^10a)R^10c to amidoxime Γ, which can be derivatized to compounds I wherein R⁹ is different from hydrogen, e.g. by reaction with an alkylating agent, such as a dialkylsulfate, an alkyliodide and the like. This reaction sequence is shown in scheme 12 below. Alternatively, compound V can be reacted with a hydroxylamine derivative NH2OR⁹, followed by treatment with NCS and an amine NH(R^10a)R^10c to yield compound I.

Scheme 12

(Γ)

Of course, in compounds V and VI, neither of G² or G³ is C-A.

Alternatively, compounds I wherein A is a group A¹, wherein A¹ is

-C(=NOR⁹)N(R^10a)R^10c can be prepared in analogy to the method described in

EP 1726589 by reacting a nitrile compound VII, wherein A' is CN, with a strong acid, such as HCI, and then with an anhydrous alcohol, e.g. anhydrous methanol, ethanol or isopropanol (R = methyl, ethyl or isopropyl), to the imidate VIII. This is then reacted with ammonia or an amine NH(R^10a)R^10c to the amidine IX. Subsequent reaction with hydroxylamine yields the amidoxime Γ, which can be derivatized to compounds I wherein R⁹ is different from hydrogen, e.g. by reaction with an alkylating agent, such as a dialkylsulfate, an alkyliodide and the like. This reaction sequence is shown in scheme 13 below. Alternatively, compound IX can be reacted with a hydroxylamine derivative NH2OR⁹ to yield compound I.

Scheme 13

(IX) (Ι')

Of course, in compounds VII, VIII and IX, neither of G² or G³ is C-A.

Compounds I wherein A is a group A² can be prepared by reacting an acid X

or a derivative thereof with a compound HN=M under standard amidation conditions as described for example below for the introduction of A³. Of course, in compound X, neither of G² or G³ is C-A.

Compounds HN=M wherein =M is

can for example be prepared by reacting the disulfide S(R⁹)₂ with HOSA (hydroxylamine-O-sulfonic acid, CAS 2950-43-8) see e.g. Journal of Organic Chemistry 1964, 29, 1397-1400 or Tetrahedron 1975, 31 , 3035- 3040.

Compounds I wherein A is a group A³, wherein W² is O can be prepared by reacting a compound Γ wherein A' is CI, Br, I or Otriflate with carbon monoxide in the presence of a palladium catalyst and an alcohol ROH, wherein R is Ci-C4-alkyl, to a compound of formula XI. Suitable palladium catalysts are for example those described in

PCT/EP 201 1/

Of course, in compound XI, neither of G² or G³ is C-A.

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 (SOC ) 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 DIPC (diisopropylcarbodiimide), benzotriazol derivatives, such as HATU

(0-(7-azabenzotriazol-1 -yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate), HBTU ((0-benzotriazol-1 -yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate) and HCTU (1 H-benzotriazolium-1 -[bis(dimethylamino)methylene]-5-chloro tetrafluoroborate) and phosphonium-derived activators, such as BOP ((benzotriazol-l -yloxy)-tris(dimethyl- amino)phosphonium hexafluorophosphate), Py-BOP ((benzotriazol-1 -yloxy)- tripyrrolidinphosphonium hexafluorophosphate) and Py-BrOP (bromotripyrrolidin- phosphonium hexafluorophosphate). Generally, the activator is used in excess. The benzotriazol and phosphonium coupling reagents are generally used in a basic medium.

In general, compounds NHR⁵R⁶ are commercially available. If compounds NHR⁵R⁶ are not commercially available, some can be prepared by reacting the chloride R⁵-CI with ammonia (if R⁶ is H) or an amine NH2R⁶, for example as described in EP-A-1736467.

Alternatively, compounds I wherein A is a group A³, wherein W² is O and wherein R⁵

with q and p being 0 (R⁵ thus being -SR⁹) can be prepared by reacting an amide XII

with Cl-S-R⁹. Of course, in compound XII, neither of G² or G³ is C-A.

Compounds Cl-S-R⁹ are in turn available by reacting the corresponding thiol HSR⁹ with a chlorinating agent, such as C , NCS, SOCI2 or SO2CI2.

Compounds I wherein A is a group A³, wherein W² is S, can be prepared by reacting the corresponding oxo-compound (W² 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 A⁴ can be prepared by standard ring coupling reactions. For example, compounds, wherein A⁴ is an N-bound heterocyclic ring can be prepared by reacting a compound Γ wherein A' is CI, Br or I with the respective ring A⁴-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-cyclohexyldiamine 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-dimethylformamide,

Ν,Ν-dimethylacetamide or N-methylpyrrolidone, and in the presence of an inorganic base such as sodium, potassium or cesium carbonate.

Compounds, wherein A⁴ is a C-bound heterocyclic ring can be prepared by reacting a compound Γ wherein A' is Br or I with the boronic acid of the respective ring A⁴-B(OH)2 or the boronate ester of the respective ring A⁴-B(OR2) under Suzuki reaction conditions via Pd-catalyzed cross coupling, such as described, for example, in WO 2007/075459. A typical catalyst is tetrakis(triphenylphosphine)palladium(0). Solvents such as tetrahydrofuran, acetonitrile, diethyl ether and dioxane are suitable. The boronic acids A⁴-B(OH)2 are either commercially available or can be prepared by known methods. Other methods for introduction of the heterocyclic groups A⁴ are the Heck, Stille, Kumada and Buchwald-Hartwig coupling procedures; see for example Tetrahedron, 2004, 60, 8991 -9016.

The ring A⁴ in A⁴-H (or in A⁴-B(OH)₂ or A⁴-B(OR₂)) can already contain the obligatory substituent SH or =S or this can be introduced after A⁴ (without the SH or =S substituent) has been attached to the "G-ring". Introduction of SH or =S can be carried out by standard procedures, such as described, for example, in WO 96/38423 or WO 2010/122167. For instance, the A⁴ ring can be first deprotonated with a strong base, e.g. an organolithium base, such as n-butyllithium, tert-butyllithium or sec-butyllithium, lithium diisopropyl amide, sodium hydride, sodium amide or potassium tert-butylate mixed with tetramethylethylene diamine (TMEDA), and then the resulting anion is reacted with elemental sulfur. Sulfur is generally used in powdered form. The reaction is generally carried out in an inert solvent, such as ethers, e.g. diethylether, methyl-tert-butylether, tetrahydrofuran or dioxane, dimethoxyethane, liquid ammonia, dimethylsulfoxide or dimethylformamide. The reaction temperature is not very critical and can range, for example, from -70 to +50°C, preferably from -70 to 0°C.

Alternatively, sulfurization can be carried out in the absence of a base by reacting the ring with elemental sulfur in a high-boiling solvent, such as N-methylpyrrolidinone, dioxane or Ν,Ν-dimethylformamide, while heating. After completion of the reaction, the resulting mixture is hydrolyzed, e.g. by the addition of water or an aqueous acid, such as a mineral acid (e.g. dilute sulfuric acid or hydrochloric acid), acetic acid or ammoniumchloride. Alternatively, in analogy to the procedure described in

WO 201 1/1 13820, the ring A⁴ (without the SH or =S substituent) can first be reacted with a Grignard reagent and then with sulfur.

Compounds wherein A is A⁵ can be prepared as described in EP-A-214241 by reacting

wherein LG is a leaving group, such as F, CI, Br, I, a sulfonate or a triflate group, with a hydrazine derivative HNR^10a-NR^10b-C(=O)R⁸ or HNR^10a-NR^10b-C(=S)R⁸. The reaction can be carried out in the presence of a base, such as a hydride, e.g. sodium hydride, a carbonate, e.g. potassium carbonate, a hydroxide, such as sodium or potassium hydroxide, an alkoxide, such as sodium methanolate or potassium tert-butanolate, an organic amine, such as triethylamine or Hunig's base, a basic N-heterocycle, such as pyridine or lutidine, and the like.

Of course, in compound XIII, neither of G² or G³ is C-A.

Alternatively, compound XIII can be first reacted with hydrazine or Boc-protected hydrazine to yield a hydrazine compound XIV

which is then submitted to an acylation with a compound LG-C(=0)-R⁸ or LG-C(=S)-R⁸, wherein LG is a leaving group, such as CI, Br or an anhydride residue(-0-C(0)-R), under amidation conditions as described above for the introduction of A³.

Of course, in compound XIV, neither of G² or G³ is C-A.

The hydrazine compound XIV can alternatively be prepared by reacting compound XIII wherein LG is CI or Br with Boc-protected hydrazine in the presence of a Cu or Pd catalyst, such as Pd(dba)2 or Cul. This reaction is preferably carried out in the presence of a base, such as cesium carbonate or potassium tert-butanolate.

The hydrazine compound XIV can alternatively be prepared by reacting an amine XV

with an amination agent, such as chloramine, an O-acyl hydroxylamine, such as O-mesitoyl hydroxylamine, an O-sulfonyl hydroxylamine or hydroxylamine O-sulfonic acid. The reaction is generally carried out in the presence of a base, such as a hydride, e.g. sodium hydride, a carbonate, e.g. potassium carbonate, a hydroxide, such as sodium or potassium hydroxide, an alkoxide, such as sodium methanolate or potassium tert-butanolate, an organic amine, such as triethylamine or Hunig's base, a basic N-heterocycle, such as pyridine or lutidine, and the like.

Of course, in compound XV, neither of G² or G³ is C-A.

The hydrazine compound XIV can alternatively be prepared by reacting an amine XV first with a nitrous compound, such as sodium nitrite or an ester of nitrous acid, such as methyl or ethyl nitrite, and then with a reduction agent, such as sodium sulfite, zinc or tin(ll) chloride.

The amine XV can be prepared from the respective nitro compound via standard reduction. Alternatively, XV can be prepared in analogy to the reaction path described in scheme 6 above from its acid X (W = O) which is first converted into its acid chloride. This is in turn converted into the corresponding acyl azide (-C(O)Ns), which is submitted to a Curtius rearrangement to give the respective isocyanate. Hydrolysis with water yields amine XV.

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 derivatization, 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. Due to their excellent activity, the compounds of the present invention may be used for controlling invertebrate pests.

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

Preferably, the method of the invention serves for protecting plant propagation material (such as seed) and the plant which grows therefrom from invertebrate pest attack or infestation and comprises treating the plant propagation material (such as seed) with a pesticidally effective amount of a compound of the present invention as defined above or with a pesticidally effective amount of an agricultural composition as defined above and below. The method of the invention is not limited to the protection of the

"substrate" (plant, plant propagation materials, soil material etc.) which has been treated according to the invention, but also has a preventive effect, thus, for example, according protection to a plant which grows from a treated plant propagation materials (such as seed), the plant itself not having been treated. Alternatively preferably, the method of the invention serves for protecting plants from attack or infestation by invertebrate pests, which method comprises treating the plants with a pesticidally effective amount of at least one compound of the invention, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof. In the sense of the present invention, "invertebrate pests" are preferably selected from arthropods and nematodes, more preferably from harmful insects, arachnids and nematodes, and even more preferably from insects, acarids and nematodes. In the sense of the present invention, "invertebrate pests" are most preferably insects. The invention further provides an agricultural composition for combating invertebrate pests, which comprises such an amount of at least one compound according to the invention and at least one inert liquid and/or solid agronomically acceptable carrier that has a pesticidal action and, if desired, at least one surfactant.

Such a composition may comprise a single active compound of the present invention or a mixture of several active compounds of the present invention. The composition according to the present invention may comprise an individual isomer or mixtures of isomers or a salt as well as individual tautomers or mixtures of tautomers. The compounds of the present invention, including their salts, stereoisomers and tautomers, are in particular suitable for efficiently controlling arthropodal pests such as arachnids, myriapedes and insects as well as nematodes. They are especially suitable for efficiently combating or controlling the following pests: Insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana,

Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea

grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella,

Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Pieris rapae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella,

Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera

canadensis; beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis,

Anthonomus pomorum, Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp., Dectes texanus texanus, Diabrotica longicornis, Diabrotica semipunctata, Diabrotica 12-punctata Diabrotica speciosa, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobius pyri, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum,

Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria; flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus,

Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga spp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, Tipula oleracea, and Tipula paludosa; thrips (Thysanoptera), e.g. Dichromothrips corbetti, Dichromothrips ssp., Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci, termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes grassei, Termes natalensis, and

Coptotermes formosanus; cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis; bugs, aphids, leafhoppers, whiteflies, scale insects, cicadas (Hemiptera), e.g.

Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Euchistus heros, Piezodorus guildini, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisia argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola,

Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzus persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantiiand, Viteus vitifolii, Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., and Arilus critatus; ants, bees, wasps, sawflies (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Lasius niger, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex californicus, Pheidole megacephala, Dasymutilla occidentalis, Bombus spp., Vespula squamosa,

Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile; crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus italicus, Chortoicetes terminifera, and Locustana pardalina; arachnoidea, such as arachnids (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Ambryomma maculatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Dermacentor andersoni, Dermacentor variabilis, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Ornithodorus moubata, Ornithodorus hermsi,

Ornithodorus turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus sanguineus, Rhipicephalus appendiculatus,

Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and Oligonychus pratensis; Araneida, e.g. Latrodectus mactans, and Loxosceles reclusa; fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus, silverfish, firebrat (Thysanura), e.g. Lepisma saccharina and Thermobia domestica, centipedes (Chilopoda), e.g. Scutigera coleoptrata, millipedes (Diplopoda), e.g. Narceus spp.,

Earwigs (Dermaptera), e.g. forficula auricularia, lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus.

Collembola (springtails), e.g. Onychiurus ssp..

The compounds of the present invention, including their salts, stereoisomers and tautomers, are also suitable for controlling nematodes : plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor,

Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and

Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other

Radopholus species; Reniform nematodes, Rotylenchus robustus and other

Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species.

The compounds of the present invention, including their salts, stereoisomers and tautomers, are particularly useful for controlling insects, preferably sucking or piercing and chewing and biting insects such as insects from the genera Lepidoptera,

Coleoptera and Hemiptera, in particular Lepidoptera, Coleoptera and true bugs.

The compounds of the present invention, including their salts, stereoisomers and tautomers, are moreover useful for controlling insects of the orders Thysanoptera, Diptera (especially flies, mosquitos), Hymenoptera (especially ants) and Isoptera (especially termites.

The compounds of the present invention, including their salts, stereoisomers and tautomers, are particularly useful for controlling insects of the orders Lepidoptera and Coleoptera.

The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.

An agrochemical composition comprises a pesticidally effective amount of a compound I. The term "effective amount" denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound I used.

The compounds I, their N-oxides and salts can be converted into customary types of agrochemical compositions, e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6^th Ed. May 2008, CropLife International.

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

Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders. Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof. Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, 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 alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes,

sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates. 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 home- 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 compound I 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

alkylisothiazolinones 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 hexacyanoferrate) 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) ad 100 wt%. The active substance dissolves upon dilution with water.

ii) Dispersible concentrates (DC)

5-25 wt% of a compound I according to the invention and 1 -10 wt% dispersant (e.g. polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclohexanone) ad

100 wt%. 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 water- insoluble organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%. 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 water ad 100 wt% 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 water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.

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

50-80 wt% of a compound I according to the invention are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt%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 solid carrier (e.g. silica gel) ad 100 wt%. 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. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

iv) 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 ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.

iv) 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 radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethene-4,4'- diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of a polyurea microcapsules. The monomers amount to 1 -10 wt%. The wt% relate to the total CS composition.

ix) Dustable powders (DP, DS)

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

x) Granules (GR, FG)

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

xi) Ultra-low volume liquids (UL)

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

The compositions types i) to xi) may optionally comprise further auxiliaries, such as 0,1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1 -1 wt% anti-foaming agents, and 0,1 -1 wt% colorants.

The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

Solutions for seed treamtent (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying compound I and compositions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the

propagation material. Preferably, compound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e.g. by seed dressing, pelleting, coating and dusting.

When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from

0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.

In treatment of plant propagation materials such as seeds, e.g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required. When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.

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

The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.

Usually, the 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 invention or partially premixed components, e.g. components comprising compounds I and/or active substances from the groups M) or F) (see below), 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 I and/or active substances from the groups M) or F) (see below), can be applied jointly (e.g. after tank mix) or consecutively.

The following categorized list M of pesticides represents insecticidal mixture partners, which are, whenever possible, classified according to the Insecticide Resistance Action Committee (IRAC), and together with which the compounds according to the present invention may be used. The combined use of the compounds of the present invention with the following pesticides may result in potential synergistic effects. The following examples of insecticidal mixing partners are provided with the intention to illustrate the possible combinations, but not to impose any limitation to the obtainable mixtures:

M.1 Acetylcholine esterase (AChE) inhibitors from the class of

M.1 A carbamates, for example aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb 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-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, meperfluthrin,metofluthrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin,

tetramethrin, tralomethrin and transfluthrin; or

M.3B sodium channel modulators such as DDT or methoxychlor;

M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class of

M.4A neonicotinoids, for example acteamiprid, chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or

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. kurstaki and 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.21A 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;

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 flubendiamide, chloranthraniliprole (rynaxypyr®), cyanthraniliprole (cyazypyr®), or

the phthalamide compounds

M.28.1 : (R)-3-Chlor-N1 -{2-methyl-4-[1 ,2,2,2-tetrafluor-1 -(trifluormethyl)ethyl]phenyl}- N2-(1 -methyl-2-methylsulfonylethyl)phthalamid and

M.28.2: (S)-3-Chlor-N1 -{2-methyl-4-[1 ,2,2,2-tetrafluor-1 -(trifluormethyl)ethyl]phenyl}- N2-(1 -methyl-2-methylsulfonylethyl)phthalamid, or the compound

M.28.3: 3-bromo-N-{2-bromo-4-chloro-6-[(1 -cyclopropylethyl)carbamoyl]phenyl}-1 -(3- chlorpyridin-2-yl)-1 H-pyrazole-5-carboxamide, 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;

M.X insecticidal active compounds of unknown or uncertain mode of action, as for example azadirachtin, amidoflumet, benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite, dicofol, flufenerim, flometoquin, fluensulfone, flupyradifurone, piperonyl butoxide, pyridalyl, pyrifluquinazon, sulfoxaflor, or the compound

M.X.1 : 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl- N-[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzamide, or the compound M.X.2: cyclopropaneacetic acid, l .l '- S^R^aR.eS.eaS.^R.^aS.^bSH-I^- cyclopropylacetyl)oxy]methyl]-1 ,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy- 4,6a, 12b-trimethyl-1 1 -oxo-9-(3-pyridinyl)-2H , 1 1 H-naphtho[2, 1 -b]pyrano[3,4-e]pyran- 3,6-diyl] ester, or the compound

M.X.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 the compound

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

2- one, or the compound

M.X.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).

The commercially available compounds of the group M listed above may be found in The Pesticide Manual, 15th Edition, C. D. S. Tomlin, British Crop Protection Council (201 1 ) among other publications.

The phthalamides M.28.1 and M.28.2 are both known from WO 2007/101540. The anthranilamide M.28.3 has been described in WO 2005/077943. The hydrazide compound M.28.4 has been described in WO 2007/043677.-The quinoline derivative flometoquin is shown in WO 2006/013896. The aminofuranone compounds

flupyradifurone is known from WO 2007/1 15644. The sulfoximine compound sulfoxaflor is known from WO 2007/149134. The isoxazoline compound M.X.1 has been described in WO 2005/085216. The pyripyropene derivative M.X.2 has been described in

WO 2006/129714. The spiroketal-substituted cyclic ketoenol derivative M.X.3 is known from WO 2006/089633 and the biphenyl-substituted spirocyclic ketoenol derivative M.X.4 from WO 2008/06791 1 . Finally triazoylphenylsulfide like M.X.5 have been described in WO 2006/043635 and biological control agents on basis of bacillus firmus in WO 2009/124707.

The following list F of active substances, in conjunction with which the compounds according to the invention can be used, is intended to illustrate the possible

combinations but does not limit them:

F.I) Respiration Inhibitors

F.1-1 ) Inhibitors of complex III at Qo site (e.g. strobilurins)

strobilurins: azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, triclopyricarb/chlorodincarb, trifloxystrobin, 2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-

3- methoxy-acrylic acid methyl ester and 2 (2-(3-(2,6-dichlorophenyl)-1 -methyl- allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N methyl-acetamide;

oxazolidinediones and imidazolinones: famoxadone, fenamidone;

F.I-2) Inhibitors of complex II (e.g. carboxamides): carboxanilides: benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, fluopy- ram, flutolanil, furametpyr, isopyrazam, isotianil, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-4 methyl-thiazole-5- carboxanilide, N-(3',4',5' trifluorobiphenyl-2 yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4 carboxamide, N-(4'-trifluoromethylthiobiphenyl-2-yl)-3 difluoromethyl-1 -methyl-1 H pyrazole-4-carboxamide and N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5 fluoro- 1 H-pyrazole-4 carboxamide;

F.I-3) Inhibitors of complex III at Qi site: cyazofamid, amisulbrom;

F.I-4) Other respiration inhibitors (complex I, uncouplers)

diflumetorim; tecnazen; ferimzone; ametoctradin; silthiofam;

nitrophenyl derivates: binapacryl, dinobuton, dinocap, fluazinam, nitrthal-isopropyl, organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide;

F.ll) Sterol biosynthesis inhibitors (SBI fungicides)

F.II-1 ) C14 demethylase inhibitors (DMI fungicides, e.g. triazoles, imidazoles) triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole;

imidazoles: imazalil, pefurazoate, oxpoconazole, prochloraz, triflumizole;

pyrimidines, pyridines and piperazines: fenarimol, nuarimol, pyrifenox, triforine;

F.II-2) Delta14-reductase inhitors (Amines, e.g. morpholines, piperidines)

morpholines: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph; piperidines: fenpropidin, piperalin;

spiroketalamines: spiroxamine;

F.II-3) Inhibitors of 3-keto reductase: hydroxyanilides: fenhexamid;

F.lll) Nucleic acid synthesis inhibitors

F.III-1 ) RNA, DNA synthesis

phenylamides or acyl amino acid fungicides: benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl;

isoxazoles and iosothiazolones: hymexazole, octhilinone;

F.III-2) DNA topisomerase inhibitors: oxolinic acid;

F.III-3) Nucleotide metabolism (e.g. adenosin-deaminase)

hydroxy (2-amino)-pyrimidines: bupirimate;

F.IV) Inhibitors of cell division and or cytoskeleton

F.IV-1 ) Tubulin inhibitors: benzimidazoles and thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl; triazolopyrimidines: 5-chloro-7 (4-methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)- [1 ,2,4]triazolo[1 ,5 a]pyrimidine

F.IV-2) Other cell division inhibitors

benzamides and phenyl acetamides: diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide;

F.IV-3) Actin inhibitors: benzophenones: metrafenone;

F.V) Inhibitors of amino acid and protein synthesis

F.V-1 ) Mmethionine synthesis inhibitors (anilino-pyrimidines)

anilino-pyrimidines: cyprodinil, mepanipyrim, nitrapyrin, pyrimethanil;

F.V-2) Protein synthesis inhibitors (anilino-pyrimidines)

antibiotics: blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxine, validamycin A;

F.VI) Signal transduction inhibitors

F.VI-1 ) MAP / Histidine kinase inhibitors (e.g. anilino-pyrimidines)

dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin;

phenylpyrroles: fenpiclonil, fludioxonil;

F.VI-2) G protein inhibitors: quinolines: quinoxyfen;

F.VI I) Lipid and membrane synthesis inhibitors

F.VI 1-1 ) Phospholipid biosynthesis inhibitors

organophosphorus compounds: edifenphos, iprobenfos, pyrazophos;

dithiolanes: isoprothiolane;

F.VII-2) Lipid peroxidation

aromatic hydrocarbons: dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole;

F.VII-3) Carboxyl acid amides (CAA fungicides)

cinnamic or mandelic acid amides: dimethomorph, flumorph, mandiproamid, pyrimorph; valinamide carbamates: benthiavalicarb, iprovalicarb, pyribencarb, valifenalate and

N-(1 -(1 -(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;

F.VII-4) Compounds affecting cell membrane permeability and fatty acides

carbamates: propamocarb, propamocarb-hydrochlorid

F.VI II) Inhibitors with Multi Site Action

F.VI 11-1 ) Inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;

F.VIII-2) Thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam,

methasulphocarb, metiram, propineb, thiram, zineb, ziram;

F.VIII-3) Organochlorine compounds (e.g. phthalimides, sulfamides, chloronitriles): anilazine, chlorothalonil, captafol, captan, folpet, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pentachlorphenole and its salts, phthalide, tolylfluanid, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide; F.VIII-4) Guanidines: guanidine, dodine, dodine free base, guazatine, guazatine- acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate);

F.VIII-5) Ahtraquinones: dithianon;

F.IX) Cell wall synthesis inhibitors

F.IX-1 ) Inhibitors of glucan synthesis: validamycin, polyoxin B;

F.IX-2) Melanin synthesis inhibitors: pyroquilon, tricyclazole, carpropamide, dicyclomet, fenoxanil;

F.X) Plant defence inducers

F.X-1 ) Salicylic acid pathway: acibenzolar-S-methyl;

F.X-2) Others: probenazole, isotianil, tiadinil, prohexadione-calcium;

phosphonates: fosetyl, fosetyl-aluminum, phosphorous acid and its salts;

F.XI) Unknown mode of action:

bronopol, chinomethionat, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat-methylsulfate, diphenylamin, flumetover, flusulfamide, flutianil, methasulfocarb, oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide, 2-but- oxy-6-iodo-3-propylchromen-4-one, N-(cyclopropylmethoxyimino-(6-difluoro-methoxy- 2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide, N'-(4-(4-chloro-3-trifluoromethyl- phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N methyl formamidine, N' (4-(4-fluoro-3-trifluoro- methyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N'-(2-methyl-5- trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, N'-(5-difluoromethyl-2 methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, 2-{1 -[2-(5-methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]-piperidin-4-yl}- thiazole-4-carboxylic acid methyl-(1 ,2,3,4-tetrahydro-naphthalen-1 -yl)-amide, 2-{1 -[2- (5-methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid methyl-(R)-1 ,2,3,4-tetrahydro-naphthalen-1 -yl-amide, methoxy-acetic acid 6-tert- butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester and N-Methyl-2-{1 -[(5-methyl-3-trifluoro- methyl-1 H-pyrazol-1 -yl)-acetyl]-piperidin-4-yl}-N-[(1 R)-1 ,2,3,4-tetrahydronaphthalen-1 - yl]-4-thiazolecarboxamide, 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyri- dine, pyrisoxazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro-pyrazole-1 carbothioic acid S-allyl ester, N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide, 5-chloro-1 (4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole, 2-(4- chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide; F.XI) Growth regulators:

abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N 6 benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5 tri iodobenzoic acid, trinexapac-ethyl and uniconazole;

F.XII) Biological control agents

antifungal biocontrol agents: Bacillus substilis strain with NRRL No. B-21661 (e.g. RHAPSODY®, SERENADE® MAX and SERENADE® ASO from AgraQuest, Inc.,

USA.), Bacillus pumilus strain with NRRL No. B-30087 (e.g. SONATA® and BALLAD® Plus from AgraQuest, Inc., USA), Ulocladium oudemansii (e.g. the product BOTRY- ZEN from BotriZen Ltd., New Zealand), Chitosan (e.g. ARMOUR-ZEN from BotriZen Ltd., New Zealand).

The invertebrate pest (also referred to as "animal pest"), i.e. the insects, arachnids and nematodes, the plant, soil or water in which the plant is growing or may grow can be contacted with the compounds of the present invention or composition(s) comprising them by any application method known in the art. As such, "contacting" includes both direct contact (applying the compounds/compositions directly on the invertebrate pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact

(applying the compounds/compositions to the locus of the invertebrate pest or plant). The compounds of the present invention or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by animal pests, especially insects, acaridae or arachnids by contacting the plant/crop with a pesticidally effective amount of compounds of the present invention. The term "crop" refers both to growing and harvested crops.

The compounds of the present invention and the compositions comprising them are particularly important in the control of a multitude of insects on various cultivated plants, such as cereal, 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.

The compounds of the present invention are employed as such or in form of compositions by treating the insects or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from insecticidal attack with an insecticidally effective amount of the active compounds. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the insects. Moreover, invertebrate pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of compounds of the present invention. As such, the application may be carried out before or after the infection of the locus, growing crops, or harvested crops by the pest.

The compounds of the present invention can also be applied preventively to places at which occurrence of the pests is expected.

The compounds of the present invention may be also used to protect growing plants from attack or infestation by pests by contacting the plant with a pesticidally effective amount of compounds of the present invention. As such, "contacting" includes both direct contact (applying the compounds/compositions directly on the pest and/or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the pest and/or plant).

"Locus" means a habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest or parasite is growing or may grow.

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 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.

Customary application rates in the protection of materials are, for example, 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.

For use in treating crop plants, the rate of application of the active ingredients of this invention may be in the range of 0.1 g to 4000 g per hectare, desirably from 5 g to 500 g per hectare, more desirably from 5 g to 200 g per hectare.

The compounds of the present invention are effective through both contact (via soil, glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait, or plant part). The compounds of the present invention may also be applied against non-crop insect pests, such as ants, termites, wasps, flies, mosquitos, crickets, or cockroaches. For use against said non-crop pests, compounds of the present invention are preferably used in a bait composition.

The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks. Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources. Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickyness, moisture retention or aging characteristics. 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 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 ingredient.

Formulations of 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 such as lower alcohols (e.g. methanol, ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g. kerosenes) having boiling ranges of approximately 50 to 250°C, dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl

orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases. 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. Suitable repellents for example are Ν,Ν-Diethyl-meta-toluamide (DEET),

Ν,Ν-diethylphenylacetamide (DEPA), 1 -(3-cyclohexan-1 -yl-carbonyl)-2-methylpiperine, (2-hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-1 ,3-hexandiol, indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insect control such as

{(+/-)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate (Esbiothrin), a repellent derived from or identical with plant extracts like limonene, eugenol,

(+)-Eucamalol (1 ), (-)-l -epi-eucamalol or crude plant extracts from plants like

Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogan nartdus (citronella). Suitable binders are selected for example from polymers and copolymers of vinyl esters of aliphatic acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate, mono- and di-ethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadiene. The impregnation of curtains and bednets is done in general by dipping the textile material into emulsions or dispersions of the insecticide or spraying them onto the nets. The compounds of the present invention and their compositions can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, 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). The compounds of the present invention are applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, plywoods, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insulating material such as styrene foams, etc. In case of application against ants doing harm to crops or human beings, the ant controller of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.

The compounds of the present invention are also suitable for the treatment of plant propagation material, especially seeds, in order to protect them from insect pest, in particular from soil-living insect pests and the resulting plant's roots and shoots against soil pests and foliar insects.

The compounds of the present invention are particularly useful for the protection of the seed from soil pests and the resulting plant's roots and shoots against soil pests and foliar insects. The protection of the resulting plant's roots and shoots is preferred. More preferred is the protection of resulting plant's shoots from piercing and sucking insects, wherein the protection from aphids is most preferred.

The present invention therefore comprises a method for the protection of seeds from insects, in particular from soil insects and of the seedlings' roots and shoots from insects, in particular from soil and foliar insects, said method comprising contacting the seeds before sowing and/or after pregermination with a compound of the present invention, including a salt thereof. Particularly preferred is a method, wherein the plant' s roots and shoots are protected, more preferably a method, wherein the plants shoots are protected form piercing and sucking insects, most preferably a method, wherein the plants shoots are protected from aphids.

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.

The term seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting.

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 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 seeds from plants, which tolerate the action of herbicides or fungicides or insecticides owing to breeding, including genetic engineering methods.

For example, the active compound can be employed in treatment of seeds from plants, which are resistant to herbicides from the group consisting of the sulfonylureas, imidazolinones, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active substances (see for example, EP-A 242 236, EP-A 242 246)

(WO 92/00377) (EP-A 257 993, U.S. 5,013,659) or in transgenic crop plants, for example cotton, with the capability of producing Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP-A 142 924, EP-A 193 259), Furthermore, the active compound can be used also for the treatment of seeds from plants, which have modified characteristics in comparison with existing plants consist, which can be generated for example by traditional breeding methods and/or the generation of mutants, or by recombinant procedures). For example, a number of cases have been described of recombinant modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO 92/1 1376, WO 92/14827, WO 91/19806) or of transgenic crop plants having a modified fatty acid composition (WO 91/13972).

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.

Compositions which are especially useful for seed treatment are e.g.:

A Soluble concentrates (SL, LS)

D Emulsions (EW, EO, ES)

E Suspensions (SC, OD, FS)

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

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

H Gel-Formulations (GF)

I Dustable powders (DP, DS)

Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, 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.

In a preferred embodiment a FS formulation is used for seed treatment. Typcially, 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 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.

Seed Treatment formulations may additionally also comprise binders and optionally colorants.

Binders can be added to improve the adhesion of the active materials on the seeds after treatment. Suitable binders are homo- and copolymers from alkylene oxides like ethylene oxide or propylene oxide, polyvinylacetate, polyvinylalcohols,

polyvinylpyrrolidones, and copolymers thereof, ethylene-vinyl acetate copolymers, acrylic homo- and copolymers, polyethyleneamines, polyethyleneamides and polyethyleneimines, polysaccharides like celluloses, tylose and starch, polyolefin homo- and copolymers like olefin/maleic anhydride copolymers, polyurethanes, polyesters, polystyrene homo and copolymers.

Optionally, also colorants can be included in the formulation. Suitable colorants or dyes for seed treatment formulations are Rhodamin B, C.I. Pigment Red 1 12, C.I. Solvent Red 1 , pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.

Examples of a gelling agent is carrageen (Satiagel^®)

In the treatment of seed, the application rates of the compounds of the present invention are generally from 0.01 g to 10 kg per 100 kg of seed, preferably from 0.05 g to 5 kg per 100 kg of seed, more preferably from 0.1 g to 1000 g per 100 kg of seed and in particular from 0.1 g to 200 g per 100 kg of seed.

The invention therefore also relates to seed comprising a compound of the present invention, including an agriculturally useful salt of it, as defined herein. The amount of the compound of the present invention, including an agriculturally useful salt thereof will in general vary from 0.01 g to 10 kg per 100 kg of seed, preferably from 0.05 g to 5 kg per 100 kg of seed, in particular from 0.1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher. Methods which can be employed for treating the seed are, in principle, all suitable seed treatment and especially seed dressing techniques known in the art, such as seed coating (e.g. seed pelleting), seed dusting and seed imbibition (e.g. seed soaking). Here, "seed treatment" refers to all methods that bring seeds and the compounds of the present invention into contact with each other, and "seed dressing" to methods of seed treatment which provide the seeds with an amount of the compounds of the present invention, i.e. which generate a seed comprising a compound of the present invention. In principle, the treatment can be applied to the seed at any time from the harvest of the seed to the sowing of the seed. The seed can be treated immediately before, or during, the planting of the seed, for example using the "planter's box" method. However, the treatment may also be carried out several weeks or months, for example up to 12 months, before planting the seed, for example in the form of a seed dressing treatment, without a substantially reduced efficacy being observed.

Expediently, the treatment is applied to unsown seed. As used herein, the term

"unsown seed" is meant to include seed at any period from the harvest of the seed to the sowing of the seed in the ground for the purpose of germination and growth of the plant.

Specifically, a procedure is followed in the treatment in which the seed is mixed, in a suitable device, for example a mixing device for solid or solid/liquid mixing partners, with the desired amount of seed treatment formulations, either as such or after previous dilution with water, until the composition is distributed uniformly on the seed. If appropriate, this is followed by a drying step. The compounds of the present invention, including their stereoisomers, veterinarily acceptable salts or N-oxides, are in particular also suitable for being used for combating parasites in and on animals.

An object of the present invention is therefore also to provide new methods to control parasites in and on animals. Another object of the invention is to provide safer pesticides for animals. Another object of the invention is further to provide pesticides for animals that may be used in lower doses than existing pesticides. And another object of the invention is to provide pesticides for animals, which provide a long residual control of the parasites.

The invention also relates to compositions comprising a parasiticidally effective amount of compounds of the present invention, including their stereoisomers, veterinarily acceptable salts or N-oxides, and an acceptable carrier, for combating parasites in and on animals.

The present invention also provides a method for treating, controlling, preventing and 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, including its stereoisomers, veterinarily acceptable salts or N-oxides, or a composition comprising it.

The invention also provides the use of a compound of the present invention, including its stereoisomers, veterinarily acceptable salts or N-oxides, for treating or protecting an animal from infestation or infection by invertebrate pests.

The invention also provides a process for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises a parasiticidally effective amount of a compound of the present invention, including its stereoisomers, veterinarily acceptable salts or N-oxides, or a composition comprising it.

Activity of compounds against agricultural pests does not suggest their suitability for control of endo- and ectoparasites in and on animals which requires, for example, low, non-emetic dosages in the case of oral application, metabolic compatibility with the animal, low toxicity, and a safe handling.

Surprisingly it has now been found that compounds of formula (I) and their

stereoisomers, veterinarily acceptable salts, tautomers and N-oxides, are suitable for combating endo- and ectoparasites in and on animals.

The compounds of the present invention, especially compounds of formula (I) and their stereoisomers, veterinarily acceptable salts, tautomers and N-oxides, and compositions comprising them are preferably used for controlling and preventing infestations of and infections in animals including warm-blooded animals (including humans) and fish. They are for example suitable for controlling and preventing infestations and infections in 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. Compounds of the present invention, including their stereoisomers, veterinarily acceptable salts or N-oxides, and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals, such as dogs or cats.

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, including their stereoisomers, veterinarily acceptable salts or N-oxides, and compositions comprising them are suitable for systemic and/or non-systemic control of ecto- and/or endoparasites. They are active against all or some stages of development.

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 canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus,

cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis,

flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex

quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrhoidalis, 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 bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes 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,

Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssus gallinae,

Actinedida (Prostigmata) und Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., and Laminosioptes spp., Bugs (Heteropterida): 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 Solenopotes spp,

Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp,

Roundworms Nematoda:

Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp,

Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp,

Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus,

Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus, and Dioctophyma renale,

Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi,

Camallanida, e.g. Dracunculus medinensis (guinea worm)

Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and

Habronema spp.,

Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp.,

Macracanthorhynchus hirudinaceus and Oncicola spp.,

Planarians (Plathelminthes): Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp.,

Trichobilharzia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp.,

Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp.

The present invention relates to the therapeutic and the non-therapeutic use of compounds of the present invention and compositions comprising them for controlling and/or combating parasites in and/or on animals. The compounds of the present invention and compositions comprising them may be used to protect the animals from attack or infestation by parasites by contacting them with a parasiticidally effective amount of compounds of the present invention and compositions containing them. The compounds of the present invention and compositions comprising them can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits). As such, "contacting" includes both direct contact (applying the pesticidal mixtures/compositions containing the compounds of the present invention directly on the parasite, which may include an indirect contact at its locus-P, and optionally also administrating the pesticidal mixtures/composition directly on the animal to be protected) 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 compounds of the present invention. "Locus-P" as used above means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal.

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 of the present 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.

The compounds of the present invention can also be applied preventively to places at which occurrence of the pests or parasites are expected.

Administration can be carried out both prophylactically and therapeutically.

Administration of the active compounds is carried out directly or in the form of suitable preparations, orally, topically/dermally or parenterally. Examples

The present invention is now illustrated in further details by the following examples, without imposing any limitation thereto.

Preparation Examples

Compounds can be characterized e.g. by coupled High Performance Liquid

Chromatography / mass spectrometry (HPLC/MS), by ¹H-NMR and/or by their melting points.

Analytical HPLC column:

Method A: Analytical UPLC column: RP-18 column Chromolith Speed ROD, 50 x 4.6 mm, from Merck KgaA, Germany). Elution: acetonitrile + 0.1 % trifluoroacetic acid (TFA) / water + 0.1 % trifluoroacetic acid (TFA) in a ratio of from 5:95 to 95:5 in 5 minutes at 40 °C. Flow: 1.8 mL/min. MS method: ESI positive.

Method B: Analytical UPLC column: Phenomenex Kinetex 1.7μ XB-C18 100; 50 x 2.1 mm from Phenomenex, Germany. Elution: acetonitrile + 0.1 % trifluoroacetic acid (TFA) / water + 0.1 % trifluoroacetic acid (TFA) in a ratio from 5:95 to 100:0 in 1.5 min at 60°C. Flow: 0.8 mL/min to 1 mL/min in 1 .5 min. MS method: ESI positive.

1H-NMR, respectively ¹³C-NMR: The signals are characterized by chemical shift (ppm, δ [delta]) vs. tetramethylsilane, respectively CDC for ¹³C-NMR, by their multiplicity and by their integral (relative number of hydrogen atoms given). The following abbreviations are used to characterize the multiplicity of the signals: m = multiplett, q = quartett, t = triplett, d = doublet and s = singulett.

Abbreviations used are: h for hour(s), min for minute(s), r.t./room temperature for 20- 25°C, THF for tetrahydrofuran, OAc for acetate, HATU for 0-(7-Azabenzotriazol-1 -yl)- Λ/,Λ/,Λ/',Λ/'-tetramethyluronium hexafluorophosphate.

C.1 Compound examples 1

Compound examples 1 -1 to 1 -13 correspond to compounds of formula C.1 :

(C.1 )

wherein R^2a, R^2b, R^2c, R⁴, R^10a and R^10b of each synthesized compound are as defined in one row of table C.1 below. The compounds were synthesized in analogy to Synthesis Example S.1.

Table d

^{* C}C₃H₅ = cyclopropyl

C.2 Compound examples 2

C ompounds of formula C.2:

(C.2)

wherein R^2a, R^2b, R^2c, R⁴, and M of each synthesized compound are as defined row of table C.2 below.

The compounds were synthesized in analogy to Synthesis Example S.2.

Table C.2

C.3 Compound examples 3

Compound examples 3-1 to 2-24 correspond to compounds of formula C.3:

(C.3)

wherein R^2a, R^2b, R^2c, R⁴, and Y of each synthesized compound are as defined in one row of table C.3 below.

The compounds were synthesized in analogy to Synthesis Example S.2.

Table C.3

Ex. R^2a, R^2b, R^2c R⁴ -Y HPLC-MS: Method, R_t (min) &

[M+H]⁺ or

H-NMR

3-1 CF₃, H, H CF₃ A 587.10

3.777

C.4 Compound examples 4

Compound example 4-1 to 4-3 correspond to compounds of formula C.4:

wherein A of each synthesized compound is as defined in one row of table C.4 below. The compounds were synthesized in analogy to Synthesis Example S.3.

Table C.4

Synthesis Example S.1

(E)-3-[4-[(E)-(Methylcarbamoylhydrazono)methyl]-3-(trifluoromethyl)phenyl]-N-[2,2,2- trifluoro-1 -[3-(trifluoromethyl)phenyl]ethyl]prop-2-enamide

(Compound example 1 -1 ; compound of formula IA, wherein R^2a is CF3, R^2b and R^2c are hydrogen, R⁴ is CF₃ and A^a is -CH(=N-NH-C(=0)-NH-CH₃)

Step 1 : (E)-3-[4-formyl-3-(trifluoromethyl)phenyl]-N-[2,2,2-trifluoro-1 -[3- (trifluoromethyl)phenyl]ethyl]prop-2-enamide

4-[(E)-3-oxo-3-[[2,2,2-trifluoro-1 -[3-(trifluoromethyl)phenyl]ethyl]amino]prop-1 -enyl]-2- (trifluoromethyl)benzoic acid (3.7 g) in THF (50 ml.) was treated with 1 ,1 '- carbonyldiimidazole ("CDI", 1 .8 g), and the mixture was stirred at 45 °C for 2 h. Then, NaBH₄ (1 .4 g) in water (20 ml.) was added and the mixture was stirred at room temperature for 2 h. The aqueous layer was extracted with MTBE, dried (Na2S0₄), filtered, and concentrated. The obtained crude alcohol ((E)-3-[4-(hydroxymethyl)-3- (trifluoromethyl)phenyl]-N-[2,2,2-trifluoro-1 -[3-(trifluoromethyl)phenyl]ethyl]prop-2- enamide, 2.8 g) was dissolved in CH2CI2 (50 ml.) and treated with pyridinium chlorochromate ("PCC", 3.4 g) and diatomite (5 g). The mixture was stirred at room temperature overnight, then filtered, and concentrated. The residue was purified by flash chromatography on silica gel (ethyl acetate/cyclohexane) to afford the product (2.6 g). H NMR (400 MHz, CDCI₃): 10.40 (s, 1 H), 8.19-8.17 (m, 1 H), 7.93-7.60 (m, 6H), 6.70 (d,1 H), 6.51 -6.48 (m, 1 H), 6.01 -5.92 (m,1 H)

Step 2: (E)-3-[4-[(E)-(methylcarbamoylhydrazono)methyl]-3- (trifluoromethyl)phenyl]-N-[2,2,2-trifluoro-1 -[3-(trifluoromethyl)phenyl]ethy^

enamide

To a solution of the product of step 1 (0.15 g) in ethanol (15 mL) was added 1 - ammonium-3-methyl urea hydrochloride (0.05 g) and acetic acid (0.1 mL). The reaction was stirred at reflux for 3 h and overnight at room temperature. Then, the mixture was concentrated and the residue was purified by flash chromatography on silica gel (ethyl acetate/cyclohexane) to afford the product (0.15 g).

HPLC-MS (method B): 1.159 min, M = 573.3. Synthesis Example S.2

A/-(3-Methylthiazolidin-2-ylidene)-4-[(E)-3-oxo-3-[[2,2,2-trifluoro-1 -[3- (trifluoromethyl)phenyl]ethyl]amino]prop-1 -enyl]-2-(trifluoromethyl)benzamide

(Compound example 2-2; compound of formula IA, wherein R^2a is CF3, R^2b and R^2c are hydrogen, R⁴ is CF₃ and A^a is C(=0)-N=(3-methylthiazolidine-2-ylidene)

A solution of 4-[(E)-3-oxo-3-[[2,2,2-trifluoro-1 -[3-(trifluoromethyl)phenyl]ethyl]amino]- prop-1 -enyl]-2-(trifluoromethyl)benzoic acid (0.6 g) in toluene/ChbC (1 :1 , 30 mL) at room temperature was treated with DMF (1 drop) and oxalylchloride (0.31 g). The reaction was stirred at room temperature overnight, concentrated and co-evaporated with CH2CI2 (3x) to obtain the crude acyl chloride (0.64 g, 4-[(E)-3-oxo-3-[[2,2,2- trifluoro-1 -[3-(trifluoromethyl)phenyl]ethyl]amino]prop-1 -enyl]-2-(trifluoromethyl)benzoyl chloride). The crude acyl chloride (0.2 g) in CH2CI2 (5 mL) was added to a solution of 3- methyl-thiazolidinimine hydrochloride (0.06 g) and 4-(dimethylamino)pyridine ("DMAP", 0.01 g) in CH2CI2 (25 mL) at -78°C. After 30 min at -78 °C, triethylamine (0.04 g) was added, and the mixture stirred for 3 h at room temperature. Then, the reaction was concentrated, and the residue was purified by flash chromatography on silica gel (ethyl acetate/cyclohexane) to afford the product (0.07 g).

HPLC-MS (method B): 1.259 min, M = 584.4.

Synthesis Example S.3

6-Chloro-1 -ethyl-5-[(methylcarbamoylhydrazono)methyl]-N-[2,2,2-trifluoro-1 -[3- (trifluoromethyl)phenyl]ethyl]indole-2-carboxamide (Compound example 4-2; compound of formula I.C, wherein wherein R^2a is CF3, R^2b and R^2c are hydrogen, R⁴ is CI, R^N is ethyl, and A^a is -CH[=N-NH-C(=0)NHCH₃]).

Step 1 : tert-Butyl 4-amino-2-chloro-5-iodo-benzoate

A solution of iodine (50 g) in ethanol (300 mL) was added dropwise to a solution of tert- butyl 4-amino-2-chloro-benzoate (45 g, CAS 75294-49-4) and Ag₂S0₄ (60 g) in ethanol (1 L) at room temperature under N2. Then, the mixture was stirred for 45 min, filtered and concentrated. The residue was poured into saturated aqueous Na2S203 solution and extracted with ethyl acetate. The crude product was purified by flash

chromatography on silica gel (petroleum ether/ethyl acetate) to afford the product as a solid (34 g). H NMR (400 MHz, CDC ): · 8.2 (s, 1 H), 6.7 (s, 1 H), 4.5 (s, 2H), 1 .6 (s, 9H).

Step 2: 5-tert-Butoxycarbonyl-6-chloro-1 H-indole-2-carboxylic acid

A mixture of the product of step 1 (7 g), pyruvic acid (8 g) and 1 ,4- diazabicyclo[2.2.2]octan ("DABCO", 6.6 g) in DMF (100 mL) was stirred at room temperature under N2 for 10 min. Then, Pd(OAc)2 (0.25 g) was added and the mixture was heated at 100 °C for 2 h, and concentrated. The residue was dissolved in ethyl acetate and water, and the pH of the aqueous layer was adjusted to pH 5 using aqueous HCI solution. The organic layer was extracted, dried (Na2S0₄), filtered and concentrated to give the crude product (5 g). H NMR (400 MHz, CD₃OD): · 8.1 (s, 1 H), 7.5 (s, 1 H), 1.6 (s, 9H).

Step 3: 05-tert-Butyl 02-ethyl 6-chloro-1 -ethyl-indole-2,5-dicarboxylate The crude product of step 2 (40 g) in DMF (500 mL) was treated with K2CO3 (40 g), iodoethane (45 g) and stirred at 60 °C for 3 h. Then, the mixture was concentrated and the residue was dissolved in CH2CI2. The organic layer was washed with water, dried (Na2S0₄), filtered and concentrated. The crude product was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate) to afford the product (21 g). H NMR (400 MHz, CDCI3): · 8.2 (s, 1 H), 7.5 (s, 1 H), 7.3 (s, 1 H), 4.6 (q, 2H), 4.4 (q, 2H), 1 .6 (s, 9H), 1.5-1.3 (m, 6H). Step 4: 5-tert-Butoxycarbonyl-6-chloro-1 -ethyl-indole-2-carboxylic acid

The product of step 3 (21 g) and NaOH (8 g) in THF (300 mL) and water (100 mL) were stirred at 40 °C overnight. Then, the mixture was acidified to pH 6, diluted with water and extracted with ethyl acetate. The organic layer was dried (Na2S0₄), filtered and concentrated to give the crude product (18 g). H NMR (400 MHz, CD₃OD): · 8.1 (s, 1 H), 7.6 (s, 1 H), 7.3 (s, 1 H), 4.7 (q, 2H), 1.6 (s, 9H), 1.4 (t, 3H).

Step 5: tert-Butyl 6-chloro-1 -ethyl-2-[[2,2,2-trifluoro-1 -[3-(trifluoromethyl)phenyl]- ethyl]carbamoyl]indole-5-carboxylate

A solution of the product of step 4 (8 g) in CH2CI2 (50 mL) at 0°C under N2 was treated with (1 -chloro-2-methyl-propenyl)-dimethyl-amine (4.5 g, CAS 26189-59-3). After 30 min, the mixture was added dropwise to a solution of 2,2,2-trifluoro-1 -[3- (trifluoromethyl)phenyl]ethanamine (10 g, CAS, 65686-68-2) and Na₂C0₃ in CH2CI2 (100 mL). The reaction was stirred overnight at room temperature, diluted with CH2CI2, and washed with water. The organic layer was dried (Na2S0₄), filtered and

concentrated. The crude product was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate) to afford the product (8 g). H NMR (400 MHz, CDC ): · 8.0 (s, 1 H), 7.8 (s, 1 H), 7.8-7.6 (m, 3H), 7.3-7.2 (m, 1 H), 6.9 (s, 1 H), 6.0 (m, 1 H), 4.4 (m, 2H), 1.7 (s, 9H), 1 .4 (t, 3H).

Step 6: 6-Chloro-1 -ethyl-2-[[2,2,2-trifluoro-1 -[3-(trifluoromethyl)phenyl]ethyl]- carbamoyl]indole-5-carboxylic acid

The product of step 5 (5.5 g) in CH2CI2 (80 mL) was treated with trifluoroacetic acid (15 mL) and stirred at room temperature overnight. The solution was concentrated to give the crude product (5 g). H NMR (400 MHz, CD₃OD): · 8.3 (s, 1 H), 8.0 (s, 1 H), 7.9 (m, 1 H), 7.8 (m, 1 H), 7.7- 7.6 (m, 2H), 7.3 (s, 1 H), 6.2-6.1 (m, 1 H), 4.5 (q, 2H), 1 .3 (t, 3H).

Step 7: 6-chloro-1 -ethyl-5-formyl-N-[2,2,2-trifluoro-1 -[3-(trifluoromethyl)phenyl]- ethyl]indole-2-carboxamide The product of step 6 (5 g) in THF (100 ml.) at 0°C was treated with borane (1 M solution in THF, 50 ml.) and stirred at 0 °C for 2 h. Then the reaction was quenched with methanol, concentrated and the residue re-dissolved in ethyl acetate. The organic phase was washed with water, dried (Na2S04) and concentrated to give crude 6- chloro-1 -ethyl-5-(hydroxymethyl)-N-[2,2,2-trifluoro-1 -[3-(trifluoromethyl)phenyl]ethyl]- indole-2-carboxamide (4.5 g). This crude material was dissolved in THF (100 ml.) and at room temperature treated with pyridinium chlorochromate ("PCC", 4g) and stirred overnight. The mixture was filtered and concentrated. . The crude product was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate) to afford the product (2.3 g) as a solid. H NMR (400 MHz, CDCI₃): · 10.5 (s, 1 H), 8.3 (s, 1 H), 8.1 (m, 2H), 7.9-7.8 (m, 3H), 7.5 (s, 1 H), 6.3 (m, 1 H), 4.7-4.6 (m, 2H), 1 .4 (t, 3H). Step 8: 6-Chloro-1 -ethyl-5-[(methylcarbamoylhydrazono)methyl]-N-[2,2,2-trifluoro- 1 -[3-(trifluoromethyl)phenyl]ethyl]indole-2-carboxamide)

The product of step 7 (0.3 g) and 1 -amino-3-methyl-urea (70 mg, CAS 17696-95-6) in ethanol (15 ml.) were treated with acetic avid (9 drops), and stirred at 70 °C for 3 h. The reaction was concentrated and the crude product was purified by flash

chromatography on silica gel (cyclohexane/EtOAc) to afford the product (0.14 g).

HPLC-MS (method B): 1.278 min, M = 548.2.

II. Evaluation of pesticidal activity:

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

B.1 Cowpea aphid (Aphis craccivora)

Potted cowpea plants colonized with approximately 100 - 150 aphids of various stages were sprayed after the pest population had been recorded. Population reduction was assessed after 24, 72, and 120 hours.

In this test, the compounds 1 -1 , 1 -2, 1 -4, 1 -5, 2-3, 3-1 1 , and 3-12 at 500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls. B.2 Diamond back moth (Plutella xylostella)

Leaves of Chinese cabbage were dipped in test solution and air-dried. Treated leaves were placed in petri dished lined with moist filter paper. Mortality was recorded 24, 72, and 120 hours after treatment.

In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 2-1,2-2, 3-3, 3-4, 3-8, 3-11, 3-12 and 4-1 at 500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.3 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, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-13, 2-1 , 2-2, 2-3, 2-4, 2-5, 2-6, 3-1 , 3-2, 3-3, 3-4, 3-5, 3-7, 3-9, 3-10, and 3-11 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.4 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.

In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11,2-1,2- 2, 2-3, 2-4, 2-6, 3-1 , 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-11 , 3-12, and 3-14 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.5 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 was diluted to a concentration of 500 ppm (wt compound: vol diluent) in a 1 :1 mixture of acetone:water (vohvol), plus 0.01 % vol/vol Kinetic^® surfactant.

Thrips potency of each compound was evaluated by using a floral-immersion technique. Plastic petri dishes were used as test arenas. All petals of individual, intact orchid flowers were dipped into treatment solution and allowed to dry. Treated flowers were placed into individual petri dishes along with 10 - 15 adult thrips. The petri dishes were then covered with lids. All test arenas were held under continuous light and a temperature of about 28°C for duration of the assay. After 4 days, the numbers of live thrips were counted on each flower, and along inner walls of each petri dish. The level of thrips mortality was extrapolated from pre-treatment thrips numbers. In this test, the compounds 1 -6, 1 -8, 1 -9, 2-1 , 2-2, 2-4, 2-5, 2-6, 3-3, 3-5, 3-8, 3-9, 3-10, 3-1 1 , 3-12 and 4-1 at 500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.6 Rice green leafhopper (Nephotettix virescens)

Rice seedlings were cleaned and washed 24 hours before spraying. The active compounds were formulated in 50:50 acetone:water (vohvol), and 0.1 % vol/vol surfactant (EL 620) was added. Potted rice seedlings were sprayed with 5 ml test solution, air dried, placed in cages and inoculated with 10 adults. Treated rice plants were kept at about 28-29°C and relative humidity of about 50-60%. Percent mortality was recorded after 72 hours.

In this test, the compound 1 -7 at 500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.7 Southern armyworm (Spodoptera eridania)

The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01 % (v/v). Lima bean plants (variety Sieva) were grown 2 plants to a pot and selected for treatment at the 1 ^st true leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into perforated plastic bags with a zip closure. About 10 to 1 1 armyworm larvae were placed into the bag and the bags zipped closed. Test plants were 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 were assessed 4 days after treatment, compared to untreated control plants.

In this test, the compounds 1 -1 , 1 -2, 1 -3, 1 -4, 1 -6, 2-1 , 2-3, 2-4, 3-4, 3-5, 3-8, and 3-1 1 at 300 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls. B.8 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.

In this test, the compounds 1 -2, 1 -1 1 , 2-1 , and 3-7 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.9 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.

In this test, the compounds 1-1 , 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-11, 1-12, 2-2,2- 6, 3-4, 3-5, 3-8, 3-10, and 3-11 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.10 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.

In this test, the compounds 1-1 , 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 2-1,2-2, 2-3, 2-4, 2-5, 2-6, 3-1,3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3- 13, and 3-14 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

Claims

claim:

Compounds of the formula I

wherein

A is a group A¹, A², A³, A⁴ or A⁵,

wherein

A¹ is selected from the group consisting of -C(=NR⁷)R⁸, and

-C(=NOR⁹)N(R ^0a)R ^0c; is a group of following formula:

wherein

# denotes the bond to the remainder of the molecule; W is selected from O and S; and

M is selected from for =C(R⁸)₂, =S(0)_m(R⁹)₂, =S(=NR ^0a)(R )₂,

=NR ^0a and =NOR⁹;

A³ is a group of following formula:

wherein

# denotes the bond to the remainder of the molecule; and

W² is selected from O and S;

A⁴ is a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, or is a 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic or heterobicyclic ring is substituted with -SH and/or =S, and is optionally further substituted with one or more substituents R¹¹; and

A⁵ is selected from the group consisting of -NR^10a-NR^10b-C(=O)R⁸ and -NR ^0a-NR ^0b-C(=S)R⁸; is selected from O and S; is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, amino, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, wherein the aliphatic and cycloaliphatic moieties in the five last- mentioned radicals may be partially or fully halogenated and/or may be substituted by one or more radicals R⁸,

phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R¹¹, and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heteromono- or heterobicyclic ring may be substituted by one or more radicals R¹¹;

or

L and a radical R² bound in the position of B¹ or B⁵, together with the carbon atoms they are bound to, form a 5-, 6-, or 7-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO2, C=0 and C=S as ring members, wherein the ring may be substituted with 1 , 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl;

E is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals selected from Ci-C6-alkoxy, and C3-C6-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals selected from the group consisting of Ci-C6-alkyl and

Ci-C6-alkoxy;

or

E and a radical R⁴ bound in the position of G¹ or G⁵, together with the carbon atoms they are bound to, form a 5-, 6-, or 7-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO2, C=0 and C=S as ring members, wherein the ring may be substituted with 1 , 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl and Ci-C6-alkoxy;

X is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C3-C8-cycloalkyl, Ci-C6-alkoxy, C3-C8-cycloalkyl-Ci-C6-alkyl- and C1-C6- alkoxy-Ci-C6-alkyl-, wherein the aliphatic and cycloaliphatic moieties in the five last-mentioned radicals may be partially or fully halogenated;

R¹ is selected from the group consisting of Ci-C4-alkyl, C2-C4-alkenyl, C2-C4- alkynyl, C3-C6-cycloalkyl, Ci-C4-alkylsulfonyl and Ci-C4-alkoxycarbonyl, wherein the aliphatic and cycloaliphatic moieties in the six last-mentioned radicals may be partially or fully halogenated and/or may be substituted by one or more radicals selected from the group consisting of hydroxy, cyano,

Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxycarbonyl, C1-C4- alkylaminocarbonyl and Ci-C4-dialkylaminocarbonyl; each R² is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, -SF₅, Ci-C6-alkyl, Cs-Cs-cycloalkyl,

C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more radicals R⁸,

-Si(R¹²)₃, -OR⁹, -S(0)_nR⁹, -N(R ^0a)R ^0b, phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R¹¹, and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heteromono- or heterobicyclic ring may be substituted by one or more radicals R¹¹; is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6- cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl and Ci-C6-alkylsulfonyl, wherein the aliphatic and cycloaliphatic moieties in the five last-mentioned radicals may be partially or fully halogenated and/or may be substituted with one or more substituents R⁸;

R⁴ is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, -SF₅, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more radicals R⁸,

-Si(R¹²)₃, -OR⁹, -S(0)_nR⁹, -N(R ^0a)R ^0b,

phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R¹¹, and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted by one or more radicals R¹¹;

or

two radicals R⁴ bound on neighboring carbon atoms form together with the atoms to which they are bound a 5-, 6-, or 7-membered saturated, partially unsaturated or maximally unsaturated ring, where the ring may contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO2, C=0 and C=S as ring members, wherein the ring may be substituted with 1 , 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl and Ci-C6-alkoxy; is selected from -S(O)_q(=NR ^0a)_pR⁹, -SO₂[N(R ^0a)R ^0b], -P(=0)(OR⁹)₂ and -P(=S)(OR⁹)₂;

wherein q and p are independently selected from 0 and 1 ; is selected from the group consisting of hydrogen, cyano, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last- mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more substituents R⁸, -OR⁹, -N(R ^0a)R ^0b, -S(0)_nR⁹, -C(=O)N(R ^0a)N(R ^0a)R ^0b, -Si(R¹²)₃, -C(=0)R⁸, -P(=0)(OR⁹)₂, -P(=S)(OR⁹)₂,

phenyl which may be substituted with 1 , 2, 3, 4, or 5 substituents R¹¹, and a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more substituents R¹¹; or R⁵ and R⁶, together with the nitrogen atom to which they are bound, form a 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring, where the ring may further contain 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and

SO2 as ring members, wherein the heterobicyclic ring may be substituted with 1 , 2, 3, 4 or 5 substituents R¹⁷;

R⁷ is selected from the group consisting of hydrogen, cyano, Ci-Cio-alkyl, C3-C8-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last- mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more substituents R⁸, -N(R ^0a)R ^0b, -S(0)_nR⁹, -C(=O)N(R ^0a)N(R ^0a)R ^0b, -Si(R¹²)₃, -C(=0)R⁸, -P(=0)(OR⁹)₂, -P(=S)(OR⁹)₂,

phenyl which may be substituted with 1 , 2, 3, 4, or 5 substituents R¹¹, and a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more substituents R¹¹; each R⁸ is independently selected from the group consisting of cyano, azido, nitro, -SCN, -SF₅, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, where the cycloaliphatic moieties in the two last-mentioned radicals may be substituted by one or more radicals R¹³;

-Si(R¹²)₃, -OR⁹, -OSO2R⁹, -S(0)_nR⁹, -N(R ^0a)R ⁰ , -C(=0)R¹³,

-C(=O)N(R ^0a)R ⁰ , -C(=S)N(R ^0a)R ⁰ , -C(=0)OR⁹,

phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substituents R¹⁶, 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 substituents R¹⁶,

or

two R⁸ present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyl group together form a group =0,

=S(0)_mR¹⁵N(R ^4a)R ^4b, =NR ^0a, =NOR⁹; or =NN(R ^0a)R ^0b;

or

two radicals R⁸, together with the carbon atoms of an 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, where the heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, and where the carbocyclic or heterocyclic ring is optionally substituted with one or more substituents R¹⁶; and

R⁸ as a substituent on a cycloalkyl ring is additionally selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl, where the aliphatic moieties in these six radicals may be substituted by one or more radicals R¹³; and

R⁸ in the groups -C(=NR⁷)R⁸, -C(=0)R⁸, =C(R⁸)₂, -NR ^0a(NR ^0b)C(=O)R⁸ and -NR^10a(NR^10b)C(=S)R⁸ is additionally selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl, where the aliphatic moieties in the six last-mentioned radicals may be substituted by one or more radicals R¹³; or

two radicals R⁸ in the group

together with the carbon atom they are bound to , form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, where the heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, and where the carbocyclic or heterocyclic ring is optionally substituted with one or more substituents R¹⁶; each R⁹ is independently selected from the group consisting of hydrogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkyl-d-

C4-alkyl-, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more radicals R¹³,

-Ci-C₆-alkyl-C(=0)OR¹⁵, -Ci-C₆-alkyl-C(=0)N(R ^4a)R ⁴ ,

-Ci-C₆-alkyl-C(=S)N(R ^4a)R ⁴ , -Ci-C₆-alkyl-C(=NR ⁴)N(R ^4a)R ⁴ , -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 ^4a)R ^4b, -C(=S)N(R ^4a)R ^4b, -C(=0)OR¹⁵,

phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substituents R¹⁶; 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 substituents R¹⁶; and

or

two R⁹ in the group

may form together with the sulfur atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO, S0₂, C(=S) and C(=0) as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8- cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C2-C6-haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substituents R¹⁶, 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 optionally carries one or more substituents R¹⁶;

R^10a, R^10b, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, Ci-C6-alkyl, C1-C6- haloalkyl, C3-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more radicals R¹³;

-Ci-C₆-alkyl-C(=0)OR¹⁵, -Ci-C₆-alkyl-C(=0)N(R ^a)R , -Ci-C₆-alkyl- C(=S)N(R ^a)R , -Ci-C₆-alkyl-C(=NR )N(R ^a)R , Ci-C₆-alkoxy, Ci-C₆- haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio,

phenyl, optionally substituted with 1 , 2, 3 or 4 substituents R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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 substituents 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 unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen,

Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substituents R¹⁶, 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 optionally carries one or more substituents R¹⁶;

or R ^0a and R^10b together form a group =C(R¹³)₂, =S(0)_m(R¹⁵)₂,

=S(0)_mR¹⁵N(R ^4a)R ^4b, =N R¹⁴ or =NOR¹⁵;

R^10c is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more radicals R¹³;

-Ci-C₆-alkyl-C(=0)OR¹⁵, -Ci-C₆-alkyl-C(=0)N (R ^a)R , -Ci-C₆-alkyl- C(=S)N(R ^a)R , -Ci-C₆-alkyl-C(=N R )N(R ^a)R , Ci-C₆-alkoxy, Ci-C₆- haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio,

phenyl, optionally substituted with 1 , 2, 3 or 4 substituents R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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 substituents R¹⁶;

or R^10a and R^10c form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substituents R¹⁶, 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 optionally carries one or more substituents R¹⁶;

or R ^0a and R^10c together form a group =C(R¹³)₂, =S(0)_m(R¹⁵)₂,

=S(0)_mR¹⁵N(R ^4a)R ^4b, =NR¹⁴ or =NOR¹⁵; each R¹¹ is independently selected from the group consisting of halogen, cyano, azido, nitro, -SCN, -SF₅, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-C10- alkenyl, C2-Cio-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted with one or more radicals R⁸,

-OR⁹, -N(R ^0a)R ⁰ , -S(0)_nR⁹, -Si(R¹²)₃;

phenyl, optionally substituted with 1 , 2, 3, 4, or 5 substituents selected independently from R¹⁶; and

a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated aromatic heterocyclic ring comprising 1 , 2, 3 or 4 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 substituents selected independently from 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 ^4a)R ^4b, =NR¹⁴, =NOR¹⁵, or =NN(R ^4a)R ^4b;

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, wherein the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from O, S, N, NR¹⁴, NO, SO and SO2 and/or 1 or 2 groups selected from C=0, C=S and C=NR¹⁴ as ring members, and wherein the ring may be substituted by one or more radicals selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-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 substituted by 1 , 2, 3, 4 or 5 radicals R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring may be substituted by one or more radicals R¹⁶;

R¹² is independently selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl, Ci-C6-alkoxy-Ci-C6-alkyl-, C1-C6- haloalkoxy-Ci-C6-alkyl-, and

phenyl, optionally substituted with 1 , 2, 3, 4, or 5 substituents R¹⁶;

R¹³ is independently selected from the group consisting of cyano, nitro, -OH, -SH, -SCN, -SF₅, d-Ce-alkoxy, Ci-C₆-haloalkoxy, Ci-C₆-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, tert- butyldimethylsilyl,

Cs-Cs-cycloalkyl which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkyl, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo; phenyl, benzyl, pyridyl, phenoxy, where the cyclic moiety in the four last-mentioned radicals may be unsubstituted or carry 1 , 2, 3, 4 or 5 substituents R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring may be substituted by 1 , 2 or 3 substituents 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(Ci-C₆-alkyl);

and

R¹³ as a substituent on a cycloalkyl ring is additionally selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 substituents selected from CN, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo;

and

R¹³ in the groups =C(R¹³)₂, -N=C(R¹³)₂, -C(=0)R¹³, -C(=S)R¹³ and

-C(=NR¹⁴)R¹³ is additionally selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from CN, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo; each R¹⁴ is independently selected from the group consisting of hydrogen, cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from CN, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, C3-C4- cycloalkyl which may be substituted by 1 or 2 substituents selected from halogen and cyano; and oxo;

C3-C8-cycloalkyl which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moiety in the two last-mentioned radicals may be substituted by 1 or 2 substituents selected from halogen and cyano; and oxo;

phenyl, benzyl, pyridyl, phenoxy, wherein the cyclic moieties in the four last- mentioned radicals may be unsubstituted and/or carry 1 , 2 or 3 substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- haloalkoxy and (Ci-C6-alkoxy)carbonyl; and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 or 2 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 substituents 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 unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and 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 unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy and

Ci-C4-haloalkoxy; each R¹⁵ is independently selected from the group consisting of hydrogen, cyano, trimethylsilyl, triethylsilyl, ferf-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl and oxo;

C3-C8-cycloalkyl which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkyl, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, C1-C4- alkylsulfonyl and oxo;

phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 ,

2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (Ci-C6-alkoxy)carbonyl; each R¹⁶ is independently selected from the group consisting of halogen, nitro, cyano, -OH, -SH, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, ferf-butyldimethylsilyl; Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo;

C3-C8-cycloalkyl which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkyl, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo;

phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (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)Ci-C₄-alkyl;

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 unsaturated or maximally unsaturated ring, wherein the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, and wherein the ring optionally carries one or more substituents selected from halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy and

Ci-C4-haloalkoxy; each R¹⁷ is independently selected from the group consisting of halogen,

cyano, nitro, 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, wherein the aliphatic or cycloaliphatic moieties in the twelve last-mentioned radicals may be substituted by one or more radicals R⁸, and phenyl which may be substituted with 1 , 2, 3, 4 or 5 substituents R¹¹, or two radicals R¹⁷ present on the same carbon atom of a saturated ring may form together a group =0 or =S; each n is independently 0, 1 or 2; and

each m is independently 0 or 1 ; and the N-oxides, tautomers, stereoisomers and agriculturally or veterinarily acceptable salts thereof. The compounds as claimed in claim 1 , where A is A¹, where A¹ is -C(=N R⁷)R⁸, where R⁷ and R⁸ are as defined in claim 1.

The compounds as claimed in claim 2, where R⁷ in -C(=N R⁷)R⁸ is selected from hydrogen, cyano, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted with 1 , 2, 3, 4, 5 or 6 substituents R⁸; and -N R^10aR^10b; where R⁸, R^10a and R^10b are as defined in claim 1 .

The compounds as claimed in claim 3, where R⁷ in -C(=N R⁷)R⁸ is -N R^10aR^10b; where R^10a and R^10b are as defined in claim 1 .

The compounds as claimed in any of claims 2 to 4, where R⁷ in -C(=N R⁷)R⁸ is -N R^10aR^10b, where

R^10a and R^10b, independently of each other, are selected from the group

consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl,

-C(=0)N(R^14a)R¹⁴ , -C(=S)N(R^14a)R¹⁴ , phenyl which is optionally substituted with 1 , 2, 3 or 4 substituents R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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 substituents 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 unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl;

wherein R^14a, R^14b and R¹⁶ are as defined in claim 1.

The compounds as claimed in claim 5, where

R^10a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl; and R ^0b is selected from -C(=0)N(R ^4a)R ^4b, -C(=S)N(R ^4a)R ^4b, Ci-C₄-alkyl, phenyl which is optionally substituted with 1 , 2, 3 or 4 substituents R¹⁶, and a 5- or 6-membered heteroaromatic ring comprising 1 , 2 or 3 heteroatoms selected from N, O and S, as ring members, where the heteroaromatic ring is optionally substituted with one or more substituents R¹⁶, and is preferably selected from -C(=0)N(R ^4a)R ^4b and -C(=S)N(R ^4a)R ⁴ ;

wherein

each R¹⁶ is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; and

R^14a and R^14b are as defined in claim 1 ; or

R^10a and R^10b form together with the nitrogen atom they are bonded to a 5- or 6- membered saturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more substituents selected from 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 and C2-C6-haloalkynyl.

7. The compounds as claimed in any of claims 5 and 6, where

R^14a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl; and

R^14b is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moieties in the three last-mentioned radicals may carry a CN group; C1-C6- alkyl substituted with a CN group, phenyl which is optionally substituted with 1 , 2, 3 or 4 substituents each independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4- alkynyl and C2-C4-haloalkynyl; and a heterocyclic ring selected from rings of formulae E-1 to E-51

E-1 E-2 E-3 E-4 E-5

E-6 E-7 E-9

E-10 E-11 E-12 E-13 E-14

E-15 E-16 E-17 E-18 E-19

E-20 E-21 E-22 E-23 E-24

E-25 E-26 E-27 E-28 E-29

E-30 E-31 E-32 E-33 E-34

E-35

E-45 E-46 E-47 E-48 E-49

E-50 E-51 wherein denotes the bonding point to the remainder of the molecule;

k is 0, 1 , 2 or 3,

q is O, 1 or 2;

each R^16a is independently hydrogen or is R¹⁶; and

each R¹⁶ is independently selected from the group consisting of halogen,

cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy,

Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or two R¹⁶ present on the same carbon atom of a saturated ring may form together =0 or =S.

8. The compounds as claimed in any of claims 5 and 6, where

R^14a is selected from hydrogen and Ci-C4-alkyl and is in particular hydrogen; and

R^14b is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl-Ci-

C4-alkyl-, where the cycloalkyl moieties in the last-mentioned radical may carry a CN group; Ci-C4-alkyl substituted with a CN group, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

9. The compounds as claimed in any of claims 2 to 8, where R⁸ in -C(=NR⁷)R⁸ as a meaning for A¹ is selected from hydrogen and -N(R^10a)R^10b and is preferably hydrogen.

The compounds as claimed in claim 9, where R^10a and R^10b in -N(R^10a)R^10b as a meaning for R⁸ are selected, independently of each other, from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, d-Ce-alkylcarbonyl, Ci-C₆-haloalkylcarbonyl, -C(=0)N(R^14a)R^14b, -C(=S)N(R^14a)R^14b, phenyl which is optionally substituted with 1 , 2, 3 or 4 substituents R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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 substituents 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 unsaturated or maximally

unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-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 and C2-C6- haloalkynyl;

wherein R^14a, R^14b and R¹⁶ are as defined in claim 7;

and are preferably hydrogen or Ci-C6-alkyl.

The compounds as claimed in claim 1 , where A is A¹, where A¹ is

-C(=NOR⁹)N(R^10a)R^10c, where R⁹ is selected from Ci-C₆-alkyl, Ci-C₆-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl, and preferably from Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl and C3-Cs-cycloalkyl-Ci-C4-alkyl-; where R^10a and R^10c are as defined in claim 1.

The compounds as claimed in claim 1 or 1 1 , where in -C(=NOR⁹)N(R^10a)R^10c, R^10a is selected from the group consisting of hydrogen, Ci-C6-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Ci-C6-alkylcarbonyl, d-Ce-haloalkylcarbonyl, -C(=0)N(R ^4a)R ⁴ , -C(=S)N(R ^4a)R ⁴ , phenyl which is optionally substituted with 1 , 2, 3 or 4 substituents R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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 substituents R¹⁶; and

R^10c is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8- cycloalkyl, Cs-Cs-halocycloalkyl, Ci-C6-alkylcarbonyl, C1-C6- haloalkylcarbonyl, -C(=0)N(R ^4a)R ^4b, -C(=S)N(R ^4a)R ^4b, phenyl which is optionally substituted with 1 , 2, 3 or 4 substituents R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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 substituents R¹⁶; wherein R^14a, R^14b and R¹⁶ are as defined in claim 7.

The compounds as claimed in claim 1 , where A is A² and in A², W is O.

The compounds as claimed in claim 1 or 13, where M is

where R⁹ and m are as defined in claim 1 .

The compounds as claimed in claim 14, where

each R⁹ is independently selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C8-cycloalkyl, Cs-Cs-halocycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl-, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more radicals R¹³,

phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substituents R¹⁶; 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 substituents R¹⁶,

or

two R⁹ in the group

form together with the sulfur atom they are bonded to a 4-, 5-, or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N , O, S, NO, SO, SO2, C(=S) and C(=0) as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl;

wherein R¹³ and R¹⁶ are as defined in claim 1 .

The compounds as claimed in claim 15, where

each R⁹ is independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C8- cycloalkyl, Cs-Cs-halocycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, and phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substituents R¹⁶, and is in particular C1-C6- alkyl,

or

two R⁹ in the group

form together with the sulfur atom they are bonded to a 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, in particular a saturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N , O, S, NO, SO, SO2, C(=S) and C(=0) as ring members, where the heterocyclic ring optionally carries one or two substituents selected from halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl;

wherein R¹⁶ is as defined in claim 7.

The compounds as claimed in any of claims 13 to 15, where m is 0 or 1 , in particular 0.

The compounds as claimed in claim 1 or 13, where M is =S(N R^10a)(R⁹)2, where R⁹ is as defined in any of claims 1 , 15 or 16, and R^10a is as defined in claim 1 .

The compounds as claimed in claim 18, where each R⁹ is independently selected from d-Ce-alkyl or two R⁹ in the group =S(N R^10a)(R⁹)₂ form together with the sulfur atom they are bonded to a 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, in particular a saturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N , O, S, NO, SO, SO2, C(=S) and C(=0) as ring members, where the heterocyclic ring optionally carries one or two substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci- C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl; wherein R¹⁶ is as defined in claim 7.

The compounds as claimed in claim 1 or 13, where M is

where R⁸ is as defined in claim 1 .

The compounds as claimed in claim 20, where each R⁸ is independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more radicals R¹³; phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substituents R¹⁶, 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 substituents R¹⁶,

wherein R¹³ and R¹⁶ are as defined in claim 1 ; or

two radicals R⁸ in the group

together with the carbon atom they are bound to , form a 5- or 6-membered saturated carbocyclic or heterocyclic ring, where the heterocyclic ring comprises 1 , 2 or 3 heteroatoms or heteroatom groups independently selected from N , O, S, NO, SO and SO2 as ring members, and where the carbocyclic or heterocyclic ring is optionally substituted with one or more substituents R¹⁶;

wherein R¹⁶ is as defined in claim 1 .

The compounds as claimed in claim 21 , where each R⁸ is independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-C8- cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, and phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substituents R¹⁶, wherein R¹⁶ is as defined in claim 7; or

two radicals R⁸ in the group

together with the carbon atom they are bound to , form a 5- or 6-membered saturated carbocyclic or heterocyclic ring, where the heterocyclic ring comprises 1 , 2 or 3 heteroatoms or heteroatom groups independently selected from N , O, S, NO, SO and SO2 as ring members, and where the carbocyclic or heterocyclic ring is optionally substituted with one or more substituents R¹⁶; wherein R¹⁶ is as defined in claim 1 .

23. The compounds as claimed in claim 1 , where A is A³ and in A³, W² is O.

24. The compounds as claimed in claim 1 or 23, where R⁵ is -S(O)_q(=NR^10a)_pR⁹, where q and p are 0 and R⁹ is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C8- cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, Cs-Cs-halocycloalkyl, C2-C6-alkenyl,

C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more radicals R¹³, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substituents R¹⁶; 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 substituents R¹⁶; wherein R¹³ and R¹⁶ are as defined in claim 1. 25. The compounds as claimed in claim 24, where R⁹ is selected from Ci-C6-alkyl, Ci-C6-haloalkyl and a 5-, 6- or 7-membered saturated 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 substituents R¹⁶; wherein R¹⁶ is as defined in claim 7.

The compounds as claimed in claim 1 or 23, where R⁵ is -SO2[N(R^10a)R^10b], where R^10a and R^10b are independently of each other selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs- halocycloalkyl, d-Ce-alkylcarbonyl, d-Ce-haloalkylcarbonyl, -C(=0)N(R^14a)R^14b, -C(=S)N(R^14a)R^14b, phenyl which is optionally substituted with 1 , 2, 3 or 4 substituents R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 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 substituents R¹⁶;

unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyI, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6- haloalkynyl;

wherein R^14a, R^14b and R¹⁶ are as defined in claim 7;

and are preferably hydrogen or Ci-C6-alkyl and in particular Ci-C6-alkyl.

The compounds as claimed in claim 1 or 23, where R⁵ is -S(O)_q(=N R^10a)_pR⁹, where q is 0 and p is 1 , and where

R⁹ is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C8- cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, Cs-Cs-halocycloalkyI, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more radicals R¹³, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substituents R¹⁶; 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 substituents R¹⁶; and

R^10a is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C8- cycloalkyl, Cs-Cs-halocycloalkyI, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more radicals R¹³;

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

wherein n, R¹³, R^14a, R^14b, R¹⁵ and R¹⁶ are as defined in claim 1.

The compounds as claimed in claim 27, where

R⁹ is d-Ce-alkyl; and

R^10a is -S(0)₂R¹⁵, wherein R¹⁵ is Ci-C₆-alkyl.

The compounds as claimed in claim 1 or 23, where R⁵ is

or -P(=S)(OR⁹)₂, where

each R⁹ is independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C3-Cs- cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, Cs-Cs-halocycloalkyI, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more radicals R¹³, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substituents R¹⁶; 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 substituents R¹⁶; and is preferably Ci-C6-alkyl; wherein

each R¹³ is independently selected from the group consisting of cyano, nitro, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, C3-C6-cycloalkyl and C3-C6-halocycloalkyl; where R¹³ as a substituent on a cycloalkyl moiety is additionally selected from

Ci-C₄-alkyl, Ci-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C2-C4- alkynyl and C2-C4-haloalkynyl; and

each R¹⁶ is independently as defined in claim 7.

30. The compounds as claimed in any of claims 1 or 23 to 29, where R⁶ is selected from the group consisting of hydrogen, Ci-C4-alkyl, C2-C3-alkynyl, -CH2-CN and Ci-C6-alkoxy-methyl-, and preferably from hydrogen and Ci-C4-alkyl.

31 . The compounds as claimed in claim 1 or 23, where R⁵ and R⁶, together with the nitrogen atom to which they are bound, form a 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring selected from following formulae

wherein

# denotes the attachment point to C(=W²);

k is 0, 1 , 2, 3, 4 or 5;

q is 0, 1 or 2; and

each R¹⁷ is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl, or two radicals R¹⁷ present on the same carbon atom of a saturated ring may form together a group =0 or =S.

The compounds as claimed in claim 1 , where A is A⁴ and A⁴ is selected from rings of formulae D-1 to D-184

1 D-2 D-3 D-4 D-5 219

D-46 D-47 D-48 D-49

D-51 D-52 D-53 D-54

D-56 D-57 D-58 D-59

D-66 D-67

D-69 D-70 D-71 D-72

D-74 D-75 D-76 D-77

D-79 D-80 D-81 D-82



D-116 D-117 D-118 D-119 D-120

D-121 D-122 D-123 D-124 D-125

D-126 D-127 D-128 D-129 D-130

D-136 D-137 D-138 D-139 D-140

D-141 D-142 D-143 D-144 D-145

D-146 D-147 D-148 D-149 D-150

D-151 D-152 D-153 D-154 D-155

D-156 D-157 D-158 D-159 D-160

D-166 D-167 D-168 D-169 D-170

D-171 D-172 D-173 D-174 D-175

D-176 D-177 D-178 D-179 D-180

D-181 D-182 D-183 D-184

wherein denotes the bonding point to the remainder of the molecule,

k is 0, 1 , 2 or 3;

q is 0, 1 or 2;

R¹¹ is as defined in claim 1 ;

R^11a is hydrogen or has one of the meanings given in claim 1 for R¹¹, where however R^11a is not halogen; and

R^s is SH or =S;

and is preferably selected from D-59, D-63 and D-64 and is in particular D-59. The compounds as claimed in claim 32, wherein

each R¹¹ is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or two R¹¹ present on the same carbon atom of a saturated or partially unsaturated ring may form together =0.

The compounds as claimed in claim 1 , where A is A⁵ and A⁵ is

-NR ^0a-NR ^0b-C(=O)R⁸, where

R^10a and R^10b, independently of each other, are selected from hydrogen and Ci-C6-alkyl; and

R⁸ is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more radicals R¹³; phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substituents R¹⁶, 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 substituents R¹⁶,

wherein R¹³ and R¹⁶ are as defined in claim 1.

The compounds as claimed in claim 34, where

each R¹³ is independently selected from the group consisting of cyano, nitro,

Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, C1-C4- haloalkylsulfonyl, C3-C6-cycloalkyl and C3-C6-halocycloalkyl; where R¹³ as a substituent on a cycloalkyi moiety is additionally selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4- haloalkynyl; and

each R¹⁶ is independently as defined in claim 7.

36. The compounds as claimed in any of the preceding claims, where B¹ and B⁵ are CH and B², B³ and B⁴ are CR², where R² has one of the meanings given in claim 1 . 37. The compounds as claimed in claim 36, where B² is CR², where R² is not

hydrogen, and B³ and B⁴ are CR², where R² has one of the meanings given in claim 1 .

38. The compounds as claimed in any of the preceding claims, where R² is selected from hydrogen, halogen, cyano, azido, nitro, -SCN, -SF₅, Ci-C6-alkyl, C3-C8- cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more radicals R⁸, -OR⁹, -S(0)_nR⁹ and -N(R^10a)R^10b, wherein R⁸, R⁹, R^10a and R^10b are as defined in claim 1.

39. The compounds as claimed in claim 38, where R² is selected from hydrogen, halogen and Ci-C2-haloalkyl, preferably from hydrogen, F, CI, Br and CF3 and in particular from hydrogen, CF3 and CI. 40. The compounds as claimed in any of the preceding claims, where G¹, G⁴ and G⁵ are C-R⁴, preferably C-H; and G² and G³ are C-A or C-R⁴; with the proviso that one of G² and G³ is C-A.

41 . The compounds as claimed in any of the preceding claims, where G³ is C-A in case that A is A¹ , A², A³ or A⁴, and G² is C-A in case that A is A⁵.

42. The compounds as claimed in any of the preceding claims, where R⁴ is selected from hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cs-cycloalkyl, C3-C5-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkynyl, Ci-C₄-alkyl, Ci-C₄-haloalkyl, Ci-C₆-alkoxy-Ci-C₆-alkyl-, C1-C4- alkylthio and Ci-C4-haloalkylthio, and R^4b and R^4c, independently of each other, are selected from hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cs- cycloalkyl, C3-C5-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C6-alkoxy-Ci-C6-alkyl-, Ci-C4-alkylthio and Ci-C4-haloalkylthio, and preferably from hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

43. The compounds as claimed in any of the preceding claims, where R¹ is selected from Ci-C4-haloalkyl and Ci-C4-alkoxycarbonyl, and is preferably CF3.

44. The compounds as claimed in any of the preceding claims, where L is selected from hydrogen and Ci-C4-alkyl, and is preferably hydrogen. 45. The compounds as claimed in any of the preceding claims, where E is selected from hydrogen, halogen and Ci-C4-alkyl, and is preferably hydrogen.

46. The compounds as claimed in any of the preceding claims, where X is selected from hydrogen, halogen and Ci-C4-alkyl, and is preferably hydrogen.

47. The compounds as claimed in any of the preceding claims, where R³ is selected from hydrogen, Ci-C4-alkyl, C2-C3-alkynyl, -CH2-CIM and Ci-C6-alkoxy-methyl-, and preferably from hydrogen and Ci-C4-alkyl. 48. The compounds as claimed in any of the preceding claims, where Z is O.

49. The compounds as claimed in any of th .B

I.A I.B

wherein

A^a is A¹ , A², A³ or A⁴;

R^2a, R^2b and R^2c, independently of each other, have one of the meanings given any of claims 1 and 37 to 39 for R²; and

R³, R⁴, A¹ , A², A³, A⁴ and A⁵ are as defined in any of claims 1 to 35, 42 and 47. 50. The compounds as claimed in any of claims 1 to 44 and 46 to 48, of formula I .C

I.C

wherein

A^a is A¹, A², A³ or A⁴;

R^2a, R^2b and R^2c, independently of each other, have one of the meanings given in any of claims 1 and 37 to 39 for R²;

R³, R⁴, A¹, A², A³, A⁴ and A⁵ are as defined in any of claims 1 to 35, 42 and 47; and R^N is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl and C1-C6- alkoxy.

An agricultural or veterinary composition comprising at least one compound of the formula I, as defined in any of claims 1 to 50, 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.

A method for controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a plant, plant propagation material, soil, area, material or environment in which the pests are growing or may grow, or the materials, plants, plant propagation material, soils, surfaces or spaces to be protected from invertebrate pest attack or infestation with a pesticidally effective amount of at least one imine compound of the formula I as defined in any of claims 1 to 50, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.

Plant propagation material, comprising at least one compound of the formula I as defined in any of claims 1 to 50, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.

A method for treating or protecting an animal from infestation or infection by invertebrate pests which comprises bringing the animal in contact with a pesticidally effective amount of at least one compound of the formula I as defined in any of claims 1 to 50, a stereoisomer thereof and/or at least one veterinarily acceptable salt thereof.