WO2015022293A2

WO2015022293A2 - 1,3-(het)aryl-substituted pyrazole compounds

Info

Publication number: WO2015022293A2
Application number: PCT/EP2014/067165
Authority: WO
Inventors: Karsten KÖRBER; Wolfgang Von Deyn; Jochen Dietz; Arun Narine; Jean-Yves WACH; Raffael KOLLER; Joachim Dickhaut
Original assignee: Basf Se
Priority date: 2013-08-12
Filing date: 2014-08-11
Publication date: 2015-02-19
Also published as: WO2015022293A3

Abstract

The present invention relates to 1,3-aryl- or hetaryl-substituted pyrazole compounds of formula (I), wherein the variables are as defined in the claims and the description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. 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. The invention further relates to a method for preparing the pyrazole compounds of the invention.

Description

1 ,3-(Het)Aryl-substituted pyrazole compounds

Description The present invention relates to 1 ,3-aryl- or hetaryl-substituted pyrazole compounds which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. 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. The invention further relates to a method for preparing the pyrazole compounds of the invention.

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 on-going need for new agents for combating invertebrate pests, in particular insects, arachnids and nematodes.

Related insecticidal (het)aryl-substituted pyrazole compounds are described in

WO 2013/063282 and WO 2004/089910. However, these documents do not describe compounds having the characteristic substituents and substituents' arrangement as claimed in the present invention. Moreover, the compounds described in

WO 2004/089910 are said to be useful serotonin antagonists; an insecticidal activity not being mentioned.

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 1 ,3-aryl- or hetaryl- substituted pyrazole compounds of the formula I below, by their stereoisomers and by their salts, in particular their agriculturally or veterinarily acceptable salts. Therefore, in a first aspect, the invention relates to 1 ,3-aryl- or hetaryl-substituted pyrazole compounds of formula I

wherein

Q is a radical of formula Q-1 , Q-2, Q-3 or Q-4

(Q-1) (Q-2)

(Q-3) (CM) is a direct bond, -C(R^3aR^3b)-, -C(R^3aR^3b)-C(R^3aR^3b)- or -C(=B)-

J² is a direct bond, -C(R^3cR^3d)- or -C(=B)-;

X is selected from CR^3e and N; L is a single bond or is selected from the group consisting of Ci-Ci2-alkylene,

Ci-Ci2-haloalkylene, C2-Cio-alkenylene, C2-Cio-haloalkenylene, C2-C10- alkynylene, C2-Cio-haloalkynylene, Cs-Cs-cycloalkylene and C3-C8- halocycloalkylene, where the 8 aforementioned radicals can be substituted with one or more radicals R¹⁵; is a group A1 , A2, A3, A4, A5 or A6, wherein

A1 is selected from -CR^d=N-R^c , -C(=N-N(R^c )R^c2)R^d and

-C(=NR^c )N(R^c2)R^c3;

A2 is selected from -SF₅ and -SCN; and in case that L is a bond, A2 is additionally selected from -OR^a; and in case that L is a bond and X is N, A2 is additionally selected from hydrogen; and in case that L is a single bond, X is N and at least one of J¹ and J² is -C(=B)-, A2 is additionally selected from Ci-C6-alkyl and Ci-C6-haloalkyl;

A3 is selected from -S(=N-R^c1)R^a, -S(=0)(=N-R^c1)-R^a and

-C(=0)-N=S(R^a)₂;

A4 is selected from -NR^c -S-R^a, -NR^c -S(=0)-R^a, -NR^c -S(=0)₂-R^a;

-NR^c -S-N(R^c2)R^c3; -NR^c -S(=0)-N(R^c2)R^c3 and

-NR^c -S(=0)₂-N(R^c2)R^c3;

A5 is selected from -N(=C(R^d)R^b) and -N=(C(R^d)N(R^c )R^c2); and

A6 is a 3-, 4-, 5-, 6-, 7- or 8-membered non-aromatic heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, S, O, NO, SO and SO2 and optionally also 1 or 2 groups C(=0) or C(=S) as ring members, where the heterocyclic ring may be substituted by one or more radicals R¹⁶: each B is independently selected from O, S, CR^d1R^d2 and NR^c1; is selected from phenyl which may carry 1 , 2, 3, 4 or 5 radicals R^4a; a 5- or 6- membered heteroaromatic monocyclic ring and a 8-, 9- or 10-membered heteroaromatic bicyclic ring, the heteroaromatic mono- and bicyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from O, N and S as ring members, where the heteroaromatic mono- or bicyclic ring may carry 1 , 2 or 3 radicals R^4a; is selected from phenyl which may carry 1 , 2, 3, 4 or 5 radicals R^4b; a 5- or 6- membered heteroaromatic monocyclic ring and a 8-, 9- or 10-membered heteroaromatic bicyclic ring, the heteroaromatic mono- and bicyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from O, N and S as ring members, where the heteroaromatic mono- or bicyclic ring may carry 1 , 2 or 3 radicals R^4b; each R^a is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Ci-C6-alkylsulfinyl, C1-C6- alkylsulfonyl, wherein the aliphatic and cycloaliphatic moieties in the 6 aforementioned radicals may be partially or fully halogenated and/or may carry 1 or 2 sub- stituents selected from Ci-C4-alkoxy and oxo;

phenyl, benzyl and pyridyl, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Ci-C6-alkoxycarbonyl;

R^b1 and R^b2, independently of each other and independently of each occurrence, are independently selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, wherein the aliphatic and cycloaliphatic moieties in the 8 aforementioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents selected from Ci-C4-alkoxy and oxo;

phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkoxycarbonyl, C1-C6- alkylamino and di-(Ci-C6-alkyl)amino;

R^c1, R^c2 and R^c3, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, cyano, hydroxyl, Ci- C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Ci-C6-alkoxy, C2-C6- alkenyloxy, C2-C6-alkynyloxy, C3-Cs-cycloalkyloxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, wherein the aliphatic and cycloaliphatic moieties in the 10 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁸;

-C(=0)R^b, -C(=0)NR^b R^b2, -C(=S)R , -C(=S)NR R ²,

phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkoxycarbonyl, Ci-C6-alkylamino and di-(Ci-C6- alkyl)amino; or

R^c1 and R^c2, or R^c2 and R^c3, 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 which may additionally contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocylic ring may be substituted with one or more substituents selected from halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy;

R^d1 and R^d2, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, halogen, cyano, nitro, -OH, -SH, -SCN, d-Ce-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, Ci-C₆- alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, wherein the aliphatic and cycloaliphatic moieties in the 8 last-mentioned radicals may be partial ly or fully halogenated and/or may carry 1 or 2 substituents selected from C1-C4- alkoxy and oxo;

-OR^a, -NR^c R^c2, -S(0)_nR^a, -S(0)_nNR^c R^c2, -C(=0)R^b, -C(=0)NR^c R^c2, -C(=0)OR^a, -C(=S)R^b, -C(=S)NR^c R^c2, -C(=S)OR^a, -C(=S)SR^a, -C(=NR^c )R ,

-C(=NR^c1)NR^c2R^c3, phenyl, benzyl, pyridyl and phenoxy, wherein the four last- mentioned radicals may carry one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy; is selected from hydrogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl,

Cs-Ce-halocycloalkyl, carboxyl, -C(=0)R^5a, -C(=0)OR^6a and

-C(=0)NR^7aR^8a; is selected from hydrogen and Ci-C6-alkyl;

R^2a and R^2c, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, halogen, cyano,

-C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, S(0)_nR¹¹, Ci-C₆- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, Cs-Cs-cycloalkenyl, wherein the aliphatic and cycloaliphatic moieties in the 6 last- mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷;

R^2b and R^2d, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, halogen, cyano, nitro,

-C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, NR⁹R¹⁰, S(0)_nR¹¹, S(0)₂NR⁹R¹°, d-Ce-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, C₃-C₈- cycloalkyl-Ci-C4-alkyl, Cs-Cs-cycloalkenyl, wherein the aliphatic and cycloaliphatic moieties in the 6 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R⁴; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaro- matic ring may carry 1 , 2 or 3 substituents R⁴;

R^3a and R^3c, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, halogen, cyano,

-C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, OR¹², S(0)_nR¹¹, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl- Ci-C4-alkyl, Cs-Cs-cycloalkenyl, wherein the aliphatic and cycloaliphatic moieties in the 6 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷;

R^3b, R^3d and R^3e, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, halogen, cyano, nitro,

-C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, NR⁹R¹⁰, OR¹², S(0)_nR¹¹, S(0)₂NR⁹R¹⁰, d-Ce-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, Cs-Cs- cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, Cs-Cs-cycloalkenyl, wherein the aliphatic and cycloaliphatic moieties in the 6 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R⁴; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R⁴; or R^2a and R^2b, or R^2a and R^2c, or R^2c and R^2d, or R^3a and R^3b, or R^3a and R^3c, or R^3c and R^3d, or R^2a and R^3a, or R^2a and R^3c, or R^2c and R^3c, or R^2a and R^3e, or R^2c and R^3e, or R^3a and R^3e, or R^3c and R^3e, together with the carbon atoms they are bound to, may form a 3- 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated carbocyclic or heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, S0₂, C(O) and C(S) as ring members, where the carbocyclic or heterocyclic ring may carry 1 , 2 or 3 substituents selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;

R⁴, R^4a and R^4b, independently of each other and independently of each occurrence, are selected from the group consisting of halogen, cyano, nitro,

-C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, NR⁹R¹⁰, OR¹²,

S(0)_nR¹¹, S(0)₂NR⁹R¹⁰, Ci-Ce-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, Cs-Cs- cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 sub- stituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R¹³; or two radicals R⁴ or two radical R^4a or two radicals R^4b, when bound to adjacent carbon atoms, together with these carbon atoms may form a 3- 4-, 5- or 6- membered saturated, partially unsaturated or maximally unsaturated carbocyclic or heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, C(O) and C(S) as ring members, where the carbocyclic or heterocyclic ring may carry 1 , 2 or 3 substituents selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; each R⁵ is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R ³; each R^5a is independently selected from the group consisting of (hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl and C3-Cs-halocycloalkyl; each R⁶ is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R ³; each R^6a is independently selected from the group consisting of hydrogen, Ci-C6-alkyl and d-C₆-haloalkyl;

R⁷ and R⁸, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the het- eroaromatic ring may carry 1 , 2 or 3 substituents R¹³; or R⁷ and R⁸, together with the nitrogen atom they are bound to, form a 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, where the heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from O, N, S, NO, SO, SO2, C(O) and C(S) as ring members; where the heterocyclic ring may carry 1 , 2 or 3 substituents R¹³;

R^7a and R^8a, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl;

R⁹ and R¹⁰, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, -C(=0)R⁵, -C(=S)R⁵,

-C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, Ci-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆- alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R¹³; or R⁹ and R¹⁰, together with the nitrogen atom they are bound to, form a 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, where the heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from O, N, S, NO, SO, SO2, C(O) and C(S) as ring members; where the heterocyclic ring may carry 1 , 2 or 3 substituents R¹³;

R^9a and R^10a, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, -C(=0)R^5a, -C(=S)R^5a,

-C(=0)OR^6a, -C(=0)NR^7aR^8a; -C(=S)NR^7aR^8a, Ci-C₆-alkyl and Ci-C₆-haloalkyl; each R¹¹ is independently selected from Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,

Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R¹³; each R^11a is independently selected from Ci-C6-alkyl and Ci-C6-haloalkyl;

R¹² is independently selected from hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R¹³; each R^12a is independently selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl; each R¹³ is independently selected from the group consisting of halogen, cyano, nitro, -C(=0)R^5a, -C(=S)R^5a, -C(=0)OR^6a, -C(=0)NR^7aR^8a; -C(=S)NR^7aR^8a, NR^9aR^10a, OR^12a, S(0)_nR^11a, S(O)₂NR^9aR ^0a, Ci-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈- cycloalkyl and C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; or two radicals R¹³, when bound to adjacent carbon atoms, together with these carbon atoms may form a 3- 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated carbocyclic or heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, C(O) and C(S) as ring members, where the carbocyclic or heterocyclic ring may carry 1 , 2 or 3 substituents selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;

R¹⁴ is selected from the group consisting of hydrogen, halogen, cyano, nitro,

-C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, NR⁹R¹⁰, OR¹², S(0)_nR¹¹, S(0)₂NR⁹R¹⁰, d-Ce-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈- cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl and Cs-Cs-cycloalkenyl, wherein the aliphatic and cycloaliphatic moieties in the 6 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; each R¹⁵ is independently selected from cyano, nitro, -OH, -SH, -SCN, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, Ci-C6-alkylcarbonyl, C1-C6- haloalkylcarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxycarbonyl, C1-C6- alkylamino, Ci-C6-dialkylamino, Ci-C6-alkylaminocarbonyl, C1-C6- dialkylaminocarbonyl, phenyl which may carry 1 , 2, 3, 4 or 5 radicals R¹⁶; and a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, S, O, NO, SO and SO2 and optionally also 1 or 2 groups

C(=0) or C(=S) as ring members, where the heterocyclic ring may be substituted by one or more radicals R¹⁶; and

as a substituent on a cycloalkylene or halocycloalkylene moiety, R¹⁵ is additionally selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl;

R¹⁶ is independently selected from halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, Ci-C6-alkoxycarbonyl, C1-C6- haloalkoxycarbonyl, Ci-C6-alkylamino, Ci-C6-dialkylamino, C1-C6- alkylaminocarbonyl and Ci-C6-dialkylaminocarbonyl; each R¹⁷ is independently selected from halogen, cyano, nitro, OR^12a and S(0)_nR^11a; and as a substituent on a cycloalkyl, cycloalkyl-alkyl or cycloalkenyl moiety, R¹⁷ is additionally selected from Ci-C4-alkyl and Ci-C4-haloalkyl; each R¹⁸ is independently selected from cyano, nitro, OR^12a, oxo, S(0)_nR^11a, C3-C8- cycloalkyl, Cs-Cs-halocycloalkyl, where the cycloaliphatic moieties in the two last- mentioned radicals may be substituted by one or more radicals selected oxo and cyano; Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxycarbonyl, Ci-C6-alkylamino, Ci-C6-dialkylamino, C1-C6- alkylaminocarbonyl, Ci-C6-dialkylaminocarbonyl, phenyl which may carry 1 , 2, 3, 4 or 5 radicals R¹⁶; and a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially un- saturated or maximally unsaturated heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, S, O, NO, SO and SO2 and optionally also 1 or 2 groups C(=0) or C(=S) as ring members, where the heterocyclic ring may be substituted by one or more radicals R¹⁶; and as a substituent on a cycloalkyl moiety, R¹⁸ is additionally selected from

Ci-C4-alkyl and Ci-C4-haloalkyl; m is 0 or 1 ; and n is 0, 1 or 2; or the N-oxides or the tautomers or the agriculturally acceptable salts thereof; except for the compound I wherein Z¹ is 4-(trifluoromethoxy)phenyl, Z² is

2-fluorophenyl, Q is Q-1 , X is CR^3e, R^1a, R^1b, R^2a, R^2b, R^2c, R^2d, R^3e and R¹⁴ are hydrogen, J¹ and J² are CH₂, L is a bond and A is NHSO2CH3;

except for the compounds I wherein Z¹ is 4-chlorophenyl, Z² is 2-fluorophenyl, Q is Q-1 , X is CR^3e, R^1a, R^1b, R^2a, R^2b, R^2c, R^2d, R^3e and R¹⁴ are hydrogen, J¹ and J² are CH₂, L is a bond and A is 2-oxo-1 ,3-oxazolidin-3-yl or 4,5-dihydro-1 ,3-oxazol-2-yl;

except for the compound I wherein Z¹ is 3-chloro-fluorophenyl, Z² is 2-fluorophenyl, Q is Q-1 , X is CR^3e, R^1a, R¹ , R^2a, R² , R^2c, R^2d, R^3e and R¹⁴ are hydrogen, J¹ and J² are CH2, L is a bond and A is 2-oxo-1 ,3-oxazolidin-3-yl;

except for the compound I wherein Z¹ is 4-chlorophenyl, Z² is 2,4,6-trifluorophenyl, Q is Q-1 , X is CR^3e, R^1a, R¹ , R^2a, R² , R^2c, R^2d, R^3e and R¹⁴ are hydrogen, J¹ and J² are CH₂, L is a bond and A is 2-oxo-1 ,3-oxazolidin-3-yl;

except for compounds I wherein Z¹ and Z² are phenyl substituted with 1 , 2 or 3 radicals selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl and Ci-C6-alkoxy; Q is Q-1 , X is CR^3e, R^1a, R¹ , R^2a, R² , R^2c, R^2d, R^3e and R¹⁴ are hydrogen, J¹ and J² are CH₂, L is a bond and A is methylcarbonyloxy (-0-C(0)-CH₃) or methylsulfonyloxy (-0-S(0)₂-CH₃); and

except for compounds I wherein Z² is 2-furanyl, Q is Q-1 , X is N, R^1a, R^1b, R^2a, R^2b, R^2c, R^2d and R¹⁴ are hydrogen, J¹ and J² are CH2, L is a bond, A is hydrogen and Z¹ is phenyl, 3'-fluorobiphenyl-4-yl, 4'-fluorobiphenyl-4-yl or 4'-methoxybiphenyl-4-yl.

In a specific embodiment the invention relates to 1 ,3-aryl- or hetaryl-substituted pyra- zole compounds of formula I

wherein

Q is a radical of formula Q-1 , Q-2, Q-3 or Q-4

(Q-1) (Q-2)

J² is a direct bond, -C(R^3cR^3d)- or -C(=B)-;

X is selected from CR^3e and N; L is a single bond or is selected from the group consisting of Ci-Ci2-alkylene, Ci-Ci2-haloalkylene, C2-Cio-alkenylene, C2-Cio-haloalkenylene, C2-C10- alkynylene, C2-Cio-haloalkynylene, Cs-Cs-cycloalkylene and C3-C8- halocycloalkylene, where the 8 aforementioned radicals can be substituted with one or more radicals R¹⁵; is a group A1 , A2, A3, A4, A5 or A6, wherein

A1 is selected from -CR^d=N-R^c , -C(=N-N(R^c )R^c2)R^d and

-C(=NR^c )N(R^c2)R^c3;

A3 is selected from -S(=N-R^c1)R^a, -S(=0)(=N-R^c1)-R^a and

-C(=0)-N=S(R^a)₂;

A4 is selected from -NR^c -S-R^a, -NR^c -S(=0)-R^a, -NR^c -S(=0)₂-R^a;

-NR^c -S-N(R^c2)R^c3; -NR^c -S(=0)-N(R^c2)R^c3 and

-NR^c -S(=0)₂-N(R^c2)R^c3;

A5 is selected from -N(=C(R^d)R^b) and -N=(C(R^d)N(R^c )R^c2); and

A6 is a 3-, 4-, 5-, 6-, 7- or 8-membered non-aromatic heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, S, O, NO, SO and SO2 and optionally also 1 or 2 groups C(=0) or C(=S) as ring members, where the heterocyclic ring may be substituted by one or more radicals R¹⁶: each B is independently selected from O, S, CR^d1R^d2 and NR^c1; is selected from phenyl which may carry 1 , 2, 3, 4 or 5 radicals R^4a; a 5- or 6- membered heteroaromatic monocyclic ring and a 8-, 9- or 10-membered heteroaromatic bicyclic ring, the heteroaromatic mono- and bicyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from O, N and S as ring members, where the heteroaromatic mono- or bicyclic ring may carry 1 , 2 or 3 radicals R^4a; is selected from phenyl which may carry 1 , 2, 3, 4 or 5 radicals R^4b; a 5- or 6- membered heteroaromatic monocyclic ring and a 8-, 9- or 10-membered heteroaromatic bicyclic ring, the heteroaromatic mono- and bicyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from O, N and S as ring members, where the heteroaromatic mono- or bicyclic ring may carry 1 , 2 or 3 radicals R^4b; each R^a is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Ci-C6-alkylsulfinyl, C1-C6- alkylsulfonyl, wherein the aliphatic and cycloaliphatic moieties in the 6 aforemen- tioned radicals may be partially or fully halogenated and/or may carry 1 or 2 sub- stituents selected from Ci-C4-alkoxy and oxo;

phenyl, benzyl and pyridyl, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Ci-C6-alkoxycarbonyl; each R^b is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, wherein the aliphatic and cycloaliphatic moieties in the 8 aforementioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents selected from Ci-C4-alkoxy and oxo;

R^c, R^c1, R^c2 and R^c3, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, cyano, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, wherein the aliphatic and cycloaliphatic moieties in the 8 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁸;

R^c1 and R^c2, or R^c2 and R^c3, 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 which may additionally contain 1 or 2 fur- ther heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocylic ring may be substituted with one or more substituents selected from halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy; R^d, R^d1 and R^d2, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, halogen, cyano, nitro, -OH, -SH , -SCN , d-Ce-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, Ci-C₆- alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, wherein the ali- phatic and cycloaliphatic moieties in the 8 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents selected from C1-C4- alkoxy and oxo;

-OR^a, -N R^c R^c2, -S(0)_nR^a, -S(0)_nN R^c R^c2, -C(=0)R^b, -C(=0)N R^c R^c2, -C(=0)OR^a, -C(=S)R^b, -C(=S)N R^c R^c2, -C(=S)OR^a, -C(=S)SR^a, -C(=N R^c )R ,

-C(=N R^c1)N R^c2R^c3, phenyl, benzyl, pyridyl and phenoxy, wherein the four last- mentioned radicals may carry one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy; is selected from hydrogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl,

Cs-Ce-halocycloalkyl, carboxyl, -C(=0)R^5a, -C(=0)OR^6a and

-C(=0)NR^7aR^8a;

R^1b is selected from hydrogen and Ci-C6-alkyl; R^2a and R^2c, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, halogen, cyano,

-C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, NR⁹R¹⁰, S(0)_nR¹¹,

S(0)₂NR⁹R¹°, Ci-Ce-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, C₃-C₈- cycloalkyl-Ci-C4-alkyl, Cs-Cs-cycloalkenyl, wherein the aliphatic and cycloaliphatic moieties in the 6 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 sub- stituents R⁴; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R⁴; R^3a and R^3c, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, halogen, cyano,

-C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, OR¹², S(0)_nR¹¹, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl- Ci-C4-alkyl, Cs-Cs-cycloalkenyl, wherein the aliphatic and cycloaliphatic moieties in the 6 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; b, R^3d and R^3e, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, halogen, cyano, nitro,

-C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, NR⁹R¹⁰, OR¹², S(0)_nR¹¹, S(0)₂NR⁹R¹⁰, d-Ce-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, Cs-Cs- cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, Cs-Cs-cycloalkenyl, wherein the aliphatic and cycloaliphatic moieties in the 6 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R⁴; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R⁴;

R^2a and R^2b, or R^2a and R^2c, or R^2c and R^2d, or R^3a and R^3b, or R^3a and R^3c, or R^3c and R^3d, or R^2a and R^3a, or R^2a and R^3c, or R^2c and R^3c, or R^2a and R^3e, or R^2c and R^3e, or R^3a and R^3e, or R^3c and R^3e, together with the carbon atoms they are bound to, may form a 3- 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated carbocyclic or heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, S0₂, C(O) and C(S) as ring members, where the carbocyclic or heterocyclic ring may carry 1 , 2 or 3 substituents selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; R⁴, R^4a and R^4b, independently of each other and independently of each occurrence, are selected from the group consisting of halogen, cyano, nitro,

-C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, NR⁹R¹⁰, OR¹², S(0)_nR¹¹, S(0)₂NR⁹R¹⁰, Ci-Ce-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, Cs-Cs- cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R¹³; or two radicals R⁴ or two radical R^4a or two radicals R^4b, when bound to adjacent carbon atoms, together with these carbon atoms may form a 3- 4-, 5- or 6- membered saturated, partially unsaturated or maximally unsaturated carbocyclic or heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, C(O) and C(S) as ring members, where the carbocyclic or heterocyclic ring may carry 1 , 2 or 3 substituents selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; each R⁵ is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered het- eroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R¹³; each R^5a is independently selected from the group consisting of (hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl and C3-Cs-halocycloalkyl; each R⁶ is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R ³; each R^6a is independently selected from the group consisting of hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl;

R⁷ and R⁸, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the het- eroaromatic ring may carry 1 , 2 or 3 substituents R¹³; or R⁷ and R⁸, together with the nitrogen atom they are bound to, form a 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, where the heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from O, N, S, NO, SO, SO2, C(O) and C(S) as ring members; where the heterocyclic ring may carry 1 , 2 or 3 substituents R¹³; and R^8a, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl;

-C(=0)OR^6a, -C(=0)NR^7aR^8a; -C(=S)NR^7aR^8a, Ci-C₆-alkyl and Ci-C₆-haloalkyl;

R¹¹ is independently selected from Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,

Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R¹³; each R^11a is independently selected from Ci-C6-alkyl and Ci-C6-haloalkyl; each R¹² is independently selected from hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the het- eroaromatic ring may carry 1 , 2 or 3 substituents R¹³; each R^12a is independently selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl; each R¹³ is independently selected from the group consisting of halogen, cyano, nitro, -C(=0)R^5a, -C(=S)R^5a, -C(=0)OR^6a, -C(=0)NR^7aR^8a; -C(=S)NR^7aR^8a, NR^9aR^10a,

OR^12a, S(0)_nR^11a, S(O)₂NR^9aR ^0a, Ci-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, Cs-Cs- cycloalkyl and C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; or two radicals R¹³, when bound to adjacent carbon atoms, together with these carbon atoms may form a 3- 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated carbocyclic or heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N , O, S, NO, SO, SO2, C(O) and C(S) as ring members, where the carbocyclic or heterocyclic ring may carry

1 , 2 or 3 substituents selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;

S(0)_nR¹¹ , S(0)₂NR⁹R¹⁰, d-Ce-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, Cs-Cs- cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl and C3-Cs-cycloalkenyl, wherein the aliphatic and cycloaliphatic moieties in the 6 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; each R¹⁵ is independently selected from cyano, nitro, -OH, -SH, -SCN, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, Ci-C6-alkylcarbonyl, C1-C6- haloalkylcarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxycarbonyl, C1-C6- alkylamino, Ci-C6-dialkylamino, Ci-C6-alkylaminocarbonyl, C1-C6- dialkylaminocarbonyl, phenyl which may carry 1 , 2, 3, 4 or 5 radicals R¹⁶; and a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally un- saturated heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, S, O, NO, SO and SO2 and optionally also 1 or 2 groups C(=0) or C(=S) as ring members, where the heterocyclic ring may be substituted by one or more radicals R¹⁶; and

as a substituent on a cycloalkylene or halocycloalkylene moiety, R¹⁵ is additional- ly selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl,

C2-C6-alkynyl and C2-C6-haloalkynyl; each R¹⁶ is independently selected from halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl,

Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, Ci-C6-alkoxycarbonyl, C1-C6- haloalkoxycarbonyl, Ci-C6-alkylamino, Ci-C6-dialkylamino, C1-C6- alkylaminocarbonyl and Ci-C6-dialkylaminocarbonyl; each R¹⁷ is independently selected from halogen, cyano, nitro, OR^12a and S(0)_nR^11a; and as a substituent on a cycloalkyl, cycloalkyl-alkyl or cycloalkenyl moiety, R¹⁷ is additionally selected from Ci-C4-alkyl and Ci-C4-haloalkyl; each R¹⁸ is independently selected from cyano, nitro, OR^12a, oxo, S(0)_nR^11a, C3-C8- cycloalkyl, Cs-Cs-halocycloalkyl, where the cycloaliphatic moieties in the two last- mentioned radicals may be substituted by one or more radicals selected oxo and cyano; Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxycarbonyl, Ci-C6-alkylamino, Ci-C6-dialkylamino, C1-C6- alkylaminocarbonyl, Ci-C6-dialkylaminocarbonyl, phenyl which may carry 1 , 2, 3, 4 or 5 radicals R¹⁶; and a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, S, O, NO, SO and SO2 and optionally also 1 or 2 groups C(=0) or C(=S) as ring members, where the heterocyclic ring may be substituted by one or more radicals R¹⁶;

and as a substituent on a cycloalkyl moiety, R¹⁸ is additionally selected from

except for compounds I wherein Z¹ and Z² are phenyl substituted with 1 , 2 or 3 radicals selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl and Ci-C6-alkoxy; Q is Q-1 , X is CR^3e, R^1a, R¹ , R^2a, R² , R^2c, R^2d, R^3e and R¹⁴ are hydrogen, J¹ and J² are CH₂, L is a bond and A is methylcarbonyloxy (-0-C(0)-CH₃) or methylsulfonyloxy (-0-S(0)2-CH₃); and

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

The present invention also provides a veterinary composition comprising at least one compound of the formula I as defined herein, a stereoisomer thereof and/or at least one veterinarily acceptable salt thereof and at least one inert liquid and/or solid veterinary acceptable 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, cul- tivated 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 "stereoisomers" 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 R^1a, R^1b and Q (if R^1a and R^1b are different). Also, the ring carbon atoms carrying R^2a and R^2b or R^2c and R^2d or the carbon atom(s) of the groups J¹ and J² or the carbon atom of X may form centers of chirality if suitably substituted. 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). To be more precise, it relates to any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety. N-oxides of compounds I can in particular be prepared by oxidizing e.g. the ring nitrogen atom of Q or X, and/or of any nitrogen-containing heterocyclic group present in group A with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides. The person skilled in the art knows if and in which positions compounds of the present invention may form N-oxides. 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 for- mula 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 (NhV) 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, dimethylammo- nium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethyl- ammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)- ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzl- triethylammonium, 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 butyr- ate. 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 hy- drochlorids, 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 an- imals 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 trans- planting. 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). 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, acety- lated 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 hydroxyl- phenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; 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 AC- Case 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 glyphosate 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 Lib- ertyLink^® (glufosinate-tolerant, Bayer CropScience, Germany).

Furthermore, plants are also covered that are by the use of recombinant DNA tech- niques 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-hydroxysteroid 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 recep- tors); 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 capa- ble 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 Cry1 Ab and Cry3Bb1 toxins), Starlink^® (corn cultivars producing the Cry9c toxin), Her- culex^® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphino- thricin-N-Acetyltransferase [PAT]); NuCOTN^® 33B (cotton cultivars producing the Cry1 Ac toxin), Bollgard^® I (cotton cultivars producing the Cry1 Ac 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 produc- ing 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 tech- niques 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, alkylsulfi- nyl, 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 ("C1-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. Ci-C3-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, heptafluoro- propyl, 1 ,1 ,1 -trifluoroprop-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.

"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 3 ("C₂-C₃-haloalkenyl"), 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 hydro- carbon radicals having 2 to 3 ("C₂-C₃-haloalkynyl"), 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 bro- mine;

The term "cycloalkyl" as used herein refers to mono- or bi- or polycyclic saturated hydrocarbon radicals having 3 to 8 ("Cs-Cs-cycloalkyl"), in particular 3 to 6 ("C3-C6- cycloalkyl") or 3 to 5 ("C₃-C₅-cycloalkyl") or 3 to 4 ("C₃-C₄-cycloalkyl") carbon atoms. Examples of monocyclic radicals having 3 to 4 carbon atoms comprise 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, bicy- clo[2.2.2]octyl and bicyclo[3.2.1 ]octyl. Preferably, the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical. The term "halocycloalkyl" as used herein, which is also expressed as "cycloalkyl 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 ("C₃-C₅-halocycloalkyl") or 3 to 4 ("C₃-C₄-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 cycloalkyl 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 cyclopropyl methyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cy- clobutylethyl and cyclobutylpropyl, Examples for C3-C6-cycloalkyl-Ci-C4-alkyl, apart those mentioned for C3-C4-cycloalkyl-Ci-C4-alkyl, are cyclopentylmethyl, cyclopen- tylethyl, cyclopentylpropyl, 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-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 "cycloalkenyl" as used herein refers to monocyclic hydrocarbon radicals with at least one C-C double bond in the ring, which ring is however not aromatic, the hydrocarbon radicals having 3 to 8 ("Cs-Cs-cycloalkyl) carbon atoms. Examples are cy- clopropenyl, such as cycloprop-1 -enyl and cycloprop-2-yl, cyclobutenyl, such as cyclo- but-1 -enyl and cyclobut-2-enyl, cyclopentenyl, such as cyclopent-1 -enyl, cyclopent-2- enyl and cyclopent-3-enyl, cyclopentadienyl, such as cyclopenta-1 ,3-dienyl, cyclpenta- 1 ,4-dienyl and cyclpenta-2,4-dienyl, cyclohexenyl, such as cyclohex-1 -enyl, cyclohex-2- enyl and cyclohex-3-enyl, cyclohexadienyl, such as cyclohexa-1 ,3-dienyl, cyclohexa- 1 ,4-dienyl, cyclohexa-1 ,5-dienyl and cyclohexa-2,5-dienyl, cycloheptenyl, cycloheptadi- enyl, cycloheptatrienyl cyclooctenyl, cyclooctadieny, cyclooctatrienyl and cyclooctatet- raenyl.

The term "halocycloalkenyl" as used herein refers to monocyclic hydrocarbon radicals with at least one C-C double bond in the ring, which ring is however not aromatic, the hydrocarbon radicals having 3 to 8 ("Cs-Cs-halocycloalkyl") carbon atoms, and wherein some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.

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 (iso- propoxy). 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 -ethyl propoxy, 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-ethyl butoxy, 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, OCHF₂, OCF₃, OCH₂CI, OCHCI₂, OCC , 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-brom pentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.

The term "Ci-C3-alkoxy-Ci-C3-alkyl" as used herein, refers to a straight-chain or branched alkyl group having 1 to 3 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C3-alkoxy group, as defined above. The term "C1-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-C4-alkoxy-methyl" as used herein, refers to methyl in which one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above. The term "Ci-C6-alkoxy- methyl" as used herein, refers to methyl in which one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above. Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, pentyloxymethyl, hexyloxymethyl and the like.

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 difluoro- methoxymethyl (CHF2OCH2), trifluoromethoxymethyl, 1 -difluoromethoxyethyl, 1 - trifluoromethoxyethyl, 2-difluoromethoxyethyl, 2-trifluoromethoxyethyl, difluoro- methoxymethyl (CH3OCF2), 1 ,1 -difluoro-2-methoxyethyl, 2,2-difluoro-2-methoxyethyl and the like. "C2-C6-Alkenyloxy" is a C2-C6-alkenyl group, as defined above, attached via an oxygen atom. Examples are ethenyloxy, prop-1 -enyloxy, prop-2-enyloxy (allyloxy), 1 - methylethenyloxy, but-1 -enyloxy, but-2-enyloxy, but-3-enyloxy, 1 -methyl-1 - propenyloxy, 2-methyl-1 -propenyloxy, 1 -methyl-2-propenyloxy, 2-methyl-2- propenyloxy; 1 -pentenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1 -methyl-1 - butenyloxy, 2-methyl-1 -butenyloxy, 3-methyl-1 -butenyloxy, 1 -methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1 -methyl-3-butenyloxy, 2-methyl-3- butenyloxy, 3-methyl-3-butenyloxy, 1 ,1 -dimethyl-2-propenyloxy, 1 ,2-dimethyl-1 - propenyloxy, 1 ,2-dimethyl-2-propenyloxy, 1 -ethyl-1 -propenyloxy, 1 -ethyl-2-propenyloxy, 1 -hexenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5-hexenyloxy, 1 -methyl-1 - pentenyloxy, 2-methyl-1 -pentenyloxy, 3-methyl-1 -pentenyloxy, 4-methyl-1 -pentenyloxy, 1 -methyl-2-pentenyloxy, 2-methyl-2-pentenyloxy, 3-methyl-2-pentenyloxy, 4-methyl-2- pentenyloxy, 1 -methyl-3-pentenyloxy, 2-methyl-3-pentenyloxy, 3-methyl-3-pentenyloxy, 4-methyl-3-pentenyloxy, 1 -methyl-4-pentenyloxy, 2-methyl-4-pentenyloxy, 3-methyl-4- pentenyloxy, 4-methyl-4-pentenyloxy, 1 ,1 -dimethyl-2-butenyloxy, 1 ,1 -dimethyl-3- butenyloxy, 1 ,2-dimethyl-1 -butenyloxy, 1 ,2-dimethyl-2-butenyloxy, 1 ,2-dimethyl-3- butenyloxy, 1 ,3-dimethyl-1 -butenyloxy, 1 ,3-dimethyl-2-butenyloxy, 1 ,3-dimethyl-3- butenyloxy, 2,2-dimethyl-3-butenyloxy, 2, 3-dimethyl-1 -butenyloxy, 2,3-dimethyl-2- butenyloxy, 2,3-dimethyl-3-butenyloxy, 3, 3-dimethyl-1 -butenyloxy, 3,3-dimethyl-2- butenyloxy, 1 -ethyl-1 -butenyloxy, 1 -ethyl-2-butenyloxy, 1 -ethyl-3-butenyloxy, 2-ethyl-1 - butenyloxy, 2-ethyl-2-butenyloxy, 2-ethyl-3-butenyloxy, 1 ,1 ,2-trimethyl-2-propenyloxy, 1 -ethyl-1 -methyl-2-propenyloxy, 1 -ethyl-2-methyl-1 -propenyloxy, 1 -ethyl-2-methyl-2- propenyloxy and the like. "C2-C6-Haloalkenyloxy" is a C2-C6-haloalkenyl group, as defined above, attached via an oxygen atom and 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 chlorovinyloxy, 2-fluoroallyloxy, 3-fluoroallyloxy, 2-chloroallyloxy, 3- chloroallyloxy and the like.

"C2-C6-Alkynyloxy" is a C2-C6-alkynyl group, as defined above, attached via an oxygen atom. Examples are ethynyloxy, 1 -propynyloxy, 2-propynyloxy (propaegyloxy), 1 - butynyloxy, 2-butynyloxy, 3-butynyloxy, 1 -methyl-2-propynyloxy, 1 -pentynyloxy, 2- pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1 -methyl-2-butynyloxy, 1 -methyl-3- butynyloxy, 2-methyl-3-butynyloxy, 3-methyl-1 -butynyloxy, 1 ,1 -dimethyl-2-propynyloxy,

1 - ethyl-2-propynyloxy, 1 -hexynyloxy, 2-hexynyloxy, 3-hexynyloxy, 4-hexynyloxy, 5- hexynyloxy, 1 -methyl-2-pentynyloxy, 1 -methyl-3-pentynyloxy, 1 -methyl-4-pentynyloxy,

2- methyl-3-pentynyloxy, 2-methyl-4-pentynyloxy, 3-methyl-1 -pentynyloxy, 3-methyl-4- pentynyloxy, 4-methyl-1 -pentynyloxy, 4-methyl-2-pentynyloxy, 1 ,1 -dimethyl-2- butynyloxy, 1 ,1 -dimethyl-3-butynyloxy, 1 ,2-dimethyl-3-butynyloxy, 2,2-dimethyl-3- butynyloxy, 3, 3-dimethyl-1 -butynyloxy, 1 -ethyl-2-butynyloxy, 1 -ethyl-3-butynyloxy, 2- ethyl-3-butynyloxy, 1 -ethyl-1 -methyl-2-propynyloxy and the like. "C2-C6-Haloalkynyloxy" is a C2-C6-haloalkynyl group, as defined above, attached via an oxygen atom and 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 "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 (iso- propylthio). 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-Cs- 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), butyl- sulfinyl, 1 -methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfi- nyl) 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 -ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1 ,1 ,2-trimethylpropylsulfinyl, 1 ,2,2- trimethylpropylsulfinyl, 1 -ethyl-1 -methylpropylsulfinyl or 1 -ethyl-2-methylpropylsulfinyl. Ci-Ce-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, at- tached via a sulfinyl [S(O)] group. The term "Ci-C4-haloalkylsulfinyl" is a Ci-C4-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "C1-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, chlorofluorome- thylsulfinyl, 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. C1-C6- Haloalkylsulfinyl is additionally, for example, 5-fluoropentylsulfinyl, 5- chloropentylsulfinyl, 5-brompentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfi- nyl, 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 ethyl- sulfonyl. 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 (isobu- tylsulfonyl) 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 sul- fonyl [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, dichloro- fluoromethylsulfonyl, 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. C1-C4- Haloalkylsulfonyl is additionally, for example, 4-fluorobutylsulfonyl, 4- chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl. C1-C6- Haloalkylsulfonyl is additionally, for example, 5-fluoropentylsulfonyl, 5- chloropentylsulfonyl, 5-brompentylsulfonyl, 5-iodopentylsulfonyl, undecafluoropen- tylsulfonyl, 6-fluorohexylsulfonyl, 6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6- iodohexylsulfonyl or dodecafluorohexylsulfonyl.

The substituent "oxo" replaces a CH₂ group by a C(=0) group. "Carboxyl" is -C(0)OH.

The term "alkylcarbonyl" is an alkyl group attached via a carbonyl [C(=0)] group; e.g. a d-Ce-alkyl ("Ci-C₆-alkylcarbonyl"), a Ci-C₅-alkyl ("Ci-C₅-alkylcarbonyl"), preferably a Ci-C₄-alkyl ("Ci-C₄-alkylcarbonyl") or Ci-C₃-alkyl ("Ci-C₃-alkylcarbonyl") group, as de- fined above, attached via a carbonyl [C(=0)] group. Examples are acetyl (methylcar- bonyl), 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, iso- propoxycarbonyl, 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 dimethyl- amino, diethylamino, ethylmethylamino, dipropylamino, diisopropylamino, methylprop- ylamino, methylisopropylamino, ethylpropylamino, ethylisopropylamino, dibutylamino and the like.

The term "Ci-C6-alkylaminocarbonyl" is a group -C(0)-N(H)Ci-C6-alkyl. Examples are methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, isopropylaminocar- bonyl, butylaminocarbonyl and the like.

The term "di-(Ci-C6-alkyl)aminocarbonyl" is a group -C(0)-N(Ci-C6-alkyl)2. Examples are dimethylaminocarbonyl, diethylaminocarbonyl, ethylmethylaminocarbonyl, dipropyl- aminocarbonyl, diisopropylaminocarbonyl, methylpropylaminocarbonyl, methylisoprop- ylaminocarbonyl, ethylpropylaminocarbonyl, ethylisopropylaminocarbonyl, dibutyl- aminocarbonyl and the like.

C2-C₄-Alkylene is a linear or branched divalent alkyl radical having 2, 3 or 4 carbon atoms. Examples are -CH₂CH₂-, -CH(CH₃)-, -CH₂CH₂CH₂-,

-CH(CH₃)CH₂-, -CH₂CH(CH₃)-, -C(CH₃)₂-, -CH₂CH₂CH₂CH₂-, -CH(CH₃)CH₂CH₂-, -CH₂CH₂CH(CH₃)-, -C(CH₃)₂CH₂-, and -CH₂C(CH₃)₂-. Ci-C₄-Alkylene is a linear or branched divalent alkyl radical having 1 , 2, 3 or 4 carbon atoms. Examples are the radicals stated above for C₂-C₄-alkylene and further -CH₂-. Linear or branched C₂-C6- alkylene is a linear or branched divalent alkyl radical having 2, 3, 4, 5 or 6 carbon atoms. Examples, in addition to the radicals stated above for C₂-C₄-alkylene, are

-CH₂CH₂CH₂CH₂CH₂-, -CH₂CH₂CH₂CH₂CH₂CH₂- and positional isomers thereof. Ci- C6-Alkylene is a linear or branched divalent alkyl radical having 1 , 2, 3, 4, 5 or 6 carbon atoms. Examples are the radicals stated above for C₂-C6-alkylene and further -CH₂-. Linear or branched C2-C7-alkylene is a linear or branched divalent alkyl radical having 2, 3, 4, 5, 6 or 7 carbon atoms. Examples, in addition to the radicals stated above for C2-C6-alkylene, are -(Chb)?-, and positional isomers thereof. Linear or branched C2-C8- alkylene is a linear or branched divalent alkyl radical having 2, 3, 4, 5, 6, 7 or 8 carbon atoms. Examples, in addition to the radicals stated above for C2-C6-alkylene, are -

(CH2)7-, -(CH2)8-, and positional isomers thereof. d-Cs-Alkylene is a linear or branched divalent alkyl radical having 1 , 2, 3, 4, 5, 6, 7 or 8 carbon atoms. Examples are the radicals stated above for C2-Cs-alkylene and further -CH2-. Linear or branched C2-C10- alkylene is a linear or branched divalent alkyl radical having 2 to 10 carbon atoms. Ex- amples, in addition to the radicals stated above for C2-Cs-alkylene, are the higher hom- ologs with 9 or 10 carbon atoms, such as -(Chb , -(Chb) -, and positional isomers thereof. Ci-Cio-Alkylene is a linear or branched divalent alkyl radical having 1 , 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms. Examples are the radicals stated above for C2-C10- alkylene and further -CH2-. Linear or branched C2-Ci2-alkylene is a linear or branched divalent alkyl radical having 2 to 12 carbon atoms. Examples, in addition to the radicals stated above for C2-Cio-alkylene, are the higher homologs with 1 1 or 12 carbon atoms, such as -(CH2)i i-, -(CH2)i2-, and positional isomers thereof. Linear or branched C1-C12- alkylene is a linear or branched divalent alkyl radical having 1 to 12 carbon atoms. Examples are the radicals stated above for C2-Ci2-alkylene and further -CH2-.

Haloalkylene is a linear or branched divalent alkyl radical having 1 to 4 (C1-C4- haloalkylene) or 1 to 6 (Ci-C6-haloalkylene) or 1 to 8(Ci-C8-haloalkylene) or 1 to 10 (Ci-Cio-haloalkylene) or 1 to 12 (Ci-Ci2-haloalkylene) carbon atoms, in which a part or all of the hydrogen atoms are replaced by halogen atoms, especially F or CI.

Alkenylene is a linear or branched aliphatic, singly or multiply, e.g., singly or doubly, olefinically unsaturated divalent radical having for example 2 to 12 (C2-Ci2-alkenylene) or 2 to 10 (C2-Cio-alkenylene) or 2 to 8 (C2-C8-alkenylene) carbon atoms. If the radical contains more than one carbon-carbon double bond these bonds are preferably not vicinal, i.e., not allenic. Examples are -CH=CH-, -C(=CH₂)-, -CH₂-CH=CH-,

-CH=CH-CH₂, -C(CH₃)=CH-, -CH=C(CH₃)-, -CH₂-CH₂-CH=CH-, -CH₂-CH=CH-CH₂-, -CH=CH-CH₂-CH₂-, -CH(CH₃)-CH=CH-, -CH=CH-CH=CH- and the like.

Haloalkenylene is an alkenylene radical in which a part or all of the hydrogen atoms are replaced by halogen atoms, especially F or CI.

Alkynylene is a linear or branched aliphatic divalent radical having, for example, 2 to 12 (C2-Ci2-alkynylene) or 2 to 10 (C2-Cio-alkynylene) or 2 to 8 (C2-C8-alkynylene) carbon atoms and containing one or more, e.g., 1 or 2, carbon-carbon triple bonds. Examples are -C≡C-, -CH₂-C≡C-, -C≡C-CH2-,-CH2-CH₂-C≡C-, -CH₂-C≡C-CH₂-, -C≡C-CH₂-CH₂-, -CH(CH₃)-C≡C-, -C≡C-C≡C- and the like.

Haloalkynylene is an alkynylene radical in which a part or all of the hydrogen atoms replaced by halogen atoms, especially F or CI.

C3-C8-Cycloalkylene stands for a divalent monocyclic, saturated hydrocarbon group having 3 to 8 carbon ring members. Examples are cyclopropane-1 ,1 -diyl, cyclopro- pane-1 ,2-diyl, cyclobutane-1 ,1 -diyl, cyclobutane-1 ,2-diyl, cyclobutane-1 ,3-diyl, cyclo- pentane-1 ,1 -diyl, cyclopentane-1 ,2-diyl, cyclopentane-1 ,3-diyl, cyclohexane-1 ,1 -diyl, cyclohexane-1 ,2-diyl, cyclohexane-1 ,3-diyl, cyclohexane-1 ,4-diyl, cycloheptane-1 ,1 - diyl, cycloheptane-1 ,2-diyl, cycloheptane-1 ,3-diyl, cycloheptane-1 ,4-diyl, cyclooctane- 1 ,1 -diyl, cyclooctane-1 ,2-diyl, cyclooctane-1 ,3-diyl, cyclooctane-1 ,4-diyl, and cyclooc- tane-1 ,5-diyl.

Halocycloalkylene is a cycloalkylene radical in which a part or all of the hydrogen atoms are replaced by halogen atoms, especially F or CI.

The term "3-, 4-, 5-, 6-, 7- or 8-membered non-aromatic heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, S, O, NO, SO and S0₂ and optionally also 1 or 2 groups C(=0) or C(=S) as ring members" (see A6) is a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and S0₂ and optionally also 1 or 2 groups C(=0) or C(=S) as ring members, except for 5- or 6-membered maximally unsaturated heterocyclic rings (as only these are aromatic).

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. As said, maximally unsaturated 5- or 6- membered heterocyclic rings are aromatic; these are not encompassed in the definition of A6. 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-, 7- or 8-membered saturated heterocyclic ring include: Oxiranyl, thiiranyl, aziridinyl, diaziridinyl, oxetanyl, thietanyl, 1 -oxotietanyl, 1 ,1 - dioxythietanyl, azetidinyl, 1 ,3-oxazetidinyl, 1 ,3-thiazetidinyl, tetrahydrofuran-2-yl, tetra- hydrofuran-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, imid- azolidin-1 -yl, imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl, oxazol- idin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxazolidin-3-yl, isoxazolidin-4-yl, isoxazoli- din-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, hexahydro- pyridazin-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, aze- pan-1 -, -2-, -3- or -4-yl, oxepan-2-, -3-, -4- or -5-yl, hexahydro-1 ,3-diazepinyl, hexahy- dro-1 ,4-diazepinyl, hexahydro-1 ,3-oxazepinyl, hexahydro-1 ,4-oxazepinyl, hexahydro- 1 ,3-dioxepinyl, hexahydro-1 ,4-dioxepinyl, azocanyl, oxocanyl and the like.

Examples of a 3-, 4-, 5-, 6-, 7- or 8-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-d i hyd rooxazol-2-yl , 2 , 3-d i hyd rooxazol-3-yl , 2 , 3-d i hyd rooxazol-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 tetrahydropyridi- nyl, 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropy- rimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydro- pyrazinyl, 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-, 7- or 8-membered maximally unsaturated (excluding aromatic) heterocyclic ring are homoaromatic radicals, such as 1 H-azepine, 1 H-[1 ,3]- diazepine and 1 H-[1 ,4]-diazepine.

Examples for a 3- or 4-membered non-aromatic heterocyclic ring containing 1 or 2 het- eroatoms or heteroatom groups selected from N, S, O, NO, SO and SO2 and optionally also 1 group C(=0) or C(=S) as ring members (see particular embodiment of A6) are in particular 3- or 4-membered saturated heterocyclic rings containing 1 or 2 heteroatoms or heteroatom groups selected from N, S, O, SO and SO2 as ring members, such as oxiranyl, thiiranyl, aziridinyl, diaziridinyl, oxetanyl, thietanyl, 1 -oxotietanyl, 1 ,1 - dioxythietanyl, azetidinyl, 1 ,3-oxazetidinyl and 1 ,3-thiazetidinyl.

Examples for 5- or 6-membered heteroaromatic monocyclic rings containing 1 , 2, 3 or 4 heteroatoms selected from O, N and S as ring members are 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 ,2,3-triazol-1 -yl, 1 ,2,3-triazol-2-yl, 1 ,2,3-triazol-4- yl, 1 ,3,4-triazol-1 -yl, 1 ,3,4-triazol-2-yl, 1 ,3,4-triazol-3-yl, 1 ,2,3,4-tetrazol-1 -yl, 1 ,2,3,4- tetrazol-2-yl, 1 ,2,3,4-tetrazol-5-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.

Examples for a 8-, 9- or 10-membered heteroaromatic bicyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from O, N and S as ring members are:

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).

The term "3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally 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" denotes a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximum unsaturated heter- omonocyclic ring or a 8-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. 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-, 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 denotes monocyclic radicals, 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 are olefinic, having 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-, 7- or 8-membered saturated heterocyclic ring include: Oxiranyl, thiiranyl, aziridinyl, diaziridinyl, oxetanyl, thietanyl, 1 -oxothietanyl, 1 ,1 - dioxothietanyl, 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, isoxa- zolidin-2-yl, isoxazolidin-3-yl, isoxazolidin-4-yl, isoxazolidin-5-yl, thiazolidin-2-yl, thiazol- idin-3-yl, thiazolidin-4-yl, thiazolidin-5-yl, isothiazolidin-2-yl, isothiazolidin-3-yl, isothia- zolidin-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, hexahydro- pyridazin-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, ox- epan-2-, -3-, -4- or -5-yl, hexahydro-1 ,3-diazepinyl, hexahydro-1 ,4-diazepinyl, hexahy- dro-1 ,3-oxazepinyl, hexahydro-1 ,4-oxazepinyl, hexahydro-1 ,3-dioxepinyl, hexahydro- 1 ,4-dioxepinyl, azocanyl, oxocanyl and the like.

Examples of a 3-, 4-, 5-, 6-, 7- or 8-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-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl,

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

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

2,3-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 tetrahydropyridi- nyl, 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropy- rimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydro- pyrazinyl, 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, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1 ,2,3-triazol-4- yl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 1,3,4-triazol-3-yl, 1 ,2,3,4-tetrazol-1-yl, 1,2,3,4- tetrazol-2-yl, 1 ,2,3,4-tetrazol-5-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 1H-azepine, 1H-[1,3]-diazepine and 1H-[1,4]-diazepine.

Examples for an 8-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:

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.

The remarks made below concerning preferred embodiments of the variables of the compounds of formula I, especially with respect to their substituents Q, Q-1 , Q-2, Q-3, Q-4, X, L, A, A1 , A2, A3, A4, A5, A6, B, J¹, J², Z , Z², R^a, R^b, R^b , R^b2, R^c, R^c , R^c2, R^c3, R^d, Rd¹, R^d2, R^1a, R^1b, R^2a, R² , R^2c, R^2d, R^3a, R³ , R^3c, R^3d, R^3e, R⁴, R^4a, R⁴ , R⁵, R^5a, R⁶, R^6a, R⁷, R^7a, R⁸, R^8a, R⁹, R^9a, R¹⁰, R ^0a, R¹¹, R ^a, R ², R ^2a, R ³, R ⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, 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 embodiment, Q is a radical of formula Q-1. In another embodiment, Q is a radical of formula Q-2. In another embodiment, Q is a radical of formula Q-3. In another embodiment, Q is a radical of formula Q-4.

In particular, Q is a radical of formula Q-1 or Q-2. Very particularly, Q is a radical of formula Q-1 .

In particular, X is CR^3e.

CR^3e is preferably selected from hydrogen, halogen and Ci-C6-alkyl, and is in particular hydrogen.

L is preferably selected from a single bond, Ci-Ci2-alkylene, Ci-Ci2-haloalkylene,

C2-Cio-alkenylene and C2-Cio-haloalkenylene, more preferably from a single bond, Ci-Ci2-alkylene and Ci-Ci2-haloalkylene, and in particular from a single bond and

Ci-C6-alkylene. Specifically, L is a single bond.

In one embodiment, A is a group A1 and is thus selected from -CR^d=N-R^c1, -C(=N- N(R^c )R^c2)R^d and -C(=NR^c )N(R^c2)R^c3. Preferably, A1 is selected from -CR^d=N-R^c and -C(=N-N(R^c )R^c2)R^d. In a particular embodiment, A1 is a group -CR^d=N-R^c1.

In this group -CR^d=N-R^c1, R^c1 is preferably selected from Ci-C₆-alkyl, C₃-C₈-cycloalkyl and Ci-C6-alkoxy, wherein the aliphatic and cycloaliphatic moieties in the 3 last- mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 sub- stituents R¹⁸; phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy. R¹⁸ has one of the above general or, in particular, one of the below preferred meanings.

More preferably, R^c1 is selected from Ci-C6-alkyl, Cs-Cs-cycloalkyl and Ci-C6-alkoxy, wherein the aliphatic and cycloaliphatic moieties in the 3 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁸; and is in par- ticular Ci-C6-alkoxy, wherein the aliphatic moiety in this radical may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁸. R¹⁸ has one of the above general or, in particular, one of the below preferred meanings.

In an alternatively preferred embodiment, in group -CR^d=N-R^c1, R^c1 is selected from hydroxyl, Ci-C6-alkoxy, C2-C6-alkenyloxy and C2-C6-alkynyloxy, wherein the aliphatic moieties in the 3 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁸, where R¹⁸ has one of the above general or, in particular, one of the below preferred meanings. In particular, in group -CR^d=N-R^c1, R^c1 is selected from hydroxyl, Ci-C6-alkoxy, C1-C6- haloalkoxy, Ci-C6-alkoxy which carries 1 substituent R¹⁸, C2-C6-alkenyloxy, C2-C6- haloalkenyloxy, C2-C6-alkynyloxy and C2-C6-haloalkynyloxy, where R¹⁸ has one of the above general or, in particular, one of the below preferred meanings.

In the above groups, R¹⁸ is preferably selected from cyano, OH, Ci-C6-alkoxy, C1-C6- haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, C1-C6- haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, where the cycloaliphatic moieties in the two last-mentioned radicals may be substituted by one or more cyano radicals; Ci-C6-alkylcarbonyl, C1-C6- haloalkylcarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxycarbonyl, Ci-C6-alkylamino, Ci-C6-dialkylamino, Ci-C6-alkylaminocarbonyl, Ci-C6-dialkylaminocarbonyl, phenyl which may carry 1 , 2, 3, 4 or 5 radicals R¹⁶; and a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, S, O, NO, SO and SO2 and optionally also 1 or 2 groups C(=0) or C(=S) as ring members, where the heterocyclic ring may be substituted by one or more radicals R¹⁶;

and as a substituent on a cycloalkyl moiety, R¹⁸ is additionally selected from Ci-C4-alkyl and Ci-C4-haloalkyl;

where R¹⁶ has one of the above general, or, in particular, one of the below preferred meanings.

More preferably, R¹⁸ is selected from cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, where the cycloaliphatic moieties in the two last-mentioned radicals may be substituted by one or more cyano radicals; Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, phenyl which may carry 1 , 2 or 3 radicals selected from halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy; and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 hetero- atoms or heteroatom groups selected from N, S, O, NO, SO and SO2 and optionally also 1 or 2 groups C(=0) or C(=S) as ring members, where the heterocyclic ring may be substituted by 1 , 2 or 3 radicals selected from halogen, cyano, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy;

and as a substituent on a cycloalkyl moiety, R¹⁸ is additionally selected from Ci-C4-alkyl and Ci-C4-haloalkyl.

In particular, R¹⁸ is selected from cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, where the cycloaliphatic moieties in the two last- mentioned radicals may be substituted by one or more cyano radicals; and phenyl which may carry 1 , 2 or 3 radicals selected from halogen, cyano, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy;

Specifically, R¹⁸ is selected from C3-C6-cycloalkyl, C3-C6-halocycloalkyl and phenyl which may carry 1 , 2 or 3 radicals selected from halogen, cyano, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy. In group -CR^d=N-R^c1, R^d is preferably selected from hydrogen, Ci-C6-alkyl and C1-C6- haloalkyl, in particular from hydrogen and methyl, and is specifically hydrogen.

In another particular embodiment, A1 is a group -C(=N-N(R^c1)R^c2)R^d. In this group -C(=N-N(R^c1)R^c2)R^d, R^c1 is preferably selected from -C(=0)R^b,

-C(=0)NR^b R^b2, -C(=S)R^b and -C(=S)NR R ², and specifically from -C(=0)R ,

-C(=0)NR R ² and -C(=S)NR R ². In these groups, R^b is preferably selected from Ci-C6-alkyl and Ci-C6-haloalkyl, and R^b1 and R^b2, independently of each other, are preferably selected from hydrogen, C1-C6- alkyl and Ci-C6-haloalkyl.

In group -C(=N-N(R^c1)R^c2)R^d, R^c2 and R^d, independently of each other, are preferably selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl, in particular from hydrogen and methyl, and are specifically hydrogen.

In another embodiment, A is a group A2. Preferably, L is simultaneously a single bond and A2 is OR^a.

In this group OR^a, R^a is preferably selected from hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the aliphatic and cycloaliphatic moieties in the 4 aforementioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents selected from Ci-C4-alkoxy and oxo; phenyl, benzyl and pyridyl, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and C1-C6- alkoxycarbonyl. More preferably, R^a is selected from hydrogen, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the aliphatic and cycloaliphatic moie- ties in the 4 aforementioned radicals may be partially or fully halogenated and/or may carry 1 or 2 Ci-C4-alkoxy substituents; phenyl, benzyl and pyridyl, wherein the four last- mentioned radicals may carry one or more substituents selected from halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Ci-C6-alkoxycarbonyl. In another more preferred embodiment, R^a is Ci-C6-alkyl which may carry 1 oxo substitu- ent. Even more preferably, R^a is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, phenyl, benzyl and pyridyl, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- haloalkoxy and Ci-C6-alkoxycarbonyl. In another even more preferred embodiment, R^a is Ci-C6-alkyl which may carry 1 oxo substituent (especially taking the form of C1-C5- alkylcarbonyl). In particular, R^a is selected from Ci-C6-alkyl and Ci-C6-haloalkyl. In another particular embodiment, R^a is Ci-C6-alkyl which may carry 1 oxo substituent. Specifically, R^a is Ci-C4-alkyl which may carry 1 oxo substituent (especially taking the form of Ci-C3-alkylcarbonyl). In another preferred embodiment, L is a single bond, X is N, at least one of J¹ and J² is -C(=B)- and A2 is selected from Ci-C6-alkyl and Ci-C6-haloalkyl. In particular, L is a single bond, X is N, J¹ and J² are -C(=0)-, and A2 is Ci-C6-alkyl, preferably Ci-C4-alkyl. In another embodiment, A is a group A3 selected from -S(=N-R^c1)R^a, -S(=0)(=N-R^c1)- R^a and -C(=0)-N=S(R^a)₂. Preferably, A3 is -C(=0)-N=S(R^a)₂.

In this group -C(=0)-N=S(R^a)2, R^a is preferably selected from hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the aliphatic and cycloaliphatic moieties in the 4 aforementioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents selected from Ci-C4-alkoxy and oxo; phenyl, benzyl and pyridyl, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Ci-C6-alkoxycarbonyl. More preferably, R^a is selected from hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the aliphatic and cycloaliphatic moieties in the 4 aforementioned radicals may be partially or fully halogenated and/or may carry 1 or 2 Ci-C4-alkoxy substituents; phenyl, benzyl and pyridyl, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Ci-C6-alkoxycarbonyl. Even more preferably, R^a is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, phenyl, benzyl and pyridyl, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- haloalkoxy and Ci-C6-alkoxycarbonyl. In particular, R^a is selected from Ci-C6-alkyl and d-Ce-haloalkyl.

In another embodiment, A is a group A4 selected from -NR^c1-S-R^a, -NR^c1-S(=0)-R^a, -NR^c -S(=0)₂-R^a; -NR^c -S-N(R^c2)R^c3; -NR^c -S(=0)-N(R^c2)R^c3 and

-NR^c -S(=0)₂-N(R^c2)R^c3. Preferably, A4 is selected from -NR^c -S(=0)-N(R^c2)R^c3 and -NR^c -S(=0)₂-N(R^c2)R^c3.

In these groups, R^a is preferably selected from hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the aliphatic and cycloaliphatic moieties in the 4 aforementioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents selected from Ci-C4-alkoxy and oxo; phenyl, benzyl and pyridyl, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and C1-C6- alkoxycarbonyl. More preferably, R^a is selected from hydrogen, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the aliphatic and cycloaliphatic moieties in the 4 aforementioned radicals may be partially or fully halogenated and/or may carry 1 or 2 Ci-C4-alkoxy substituents; phenyl, benzyl and pyridyl, wherein the four last- mentioned radicals may carry one or more substituents selected from halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Ci-C6-alkoxycarbonyl. Even more preferably, R^a is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, phenyl, benzyl and pyridyl, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Ci-C6-alkoxycarbonyl. In particular, R^a is selected from Ci-C6-alkyl and C1-C6- haloalkyl. In these groups, R^c1, R^c2 and R^c3, independently of each other, are selected from hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Ci-C6-alkoxy, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁸;

phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may car- ry one or more substituents selected from halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkoxycarbonyl, Ci-C6-alkylamino and di-(Ci-C6-alkyl)amino.

In particular, they are selected from hydrogen, Ci-C6-alkyl which may carry 1 radical R¹⁸, d-Ce-haloalkyl and Ci-C₆-alkoxy.

In another embodiment, A is a group A5.

In another embodiment, A is a group A6. A6 is preferably selected from a 3- or 4- membered non-aromatic heterocyclic ring containing 1 or 2 heteroatoms or heteroatom groups selected from N, S, O, NO, SO and SO2 and optionally also 1 group C(=0) or C(=S) as ring members, where the heterocyclic ring may be substituted by one or more radicals R¹⁶. More preferably, A6 is selected from a 3- or 4-membered saturated heterocyclic ring containing 1 or 2 heteroatoms or heteroatom groups selected from N, S, O, SO and SO2 as ring members.

R^2a, R^2b, R^2c and R^2d, independently of each other, are preferably selected from hydrogen, halogen and Ci-C4-alkyl, more preferably from hydrogen and methyl, and are in particular hydrogen. J¹ is preferably -C(R^3aR^3b)-, and J² is preferably -C(R^3cR^3d)-.

Preferably, R^3a, R^3b, R^3c and R^3d are independently of each other selected from hydrogen, halogen and Ci-C4-alkyl, more preferably from hydrogen and methyl, and are in particular hydrogen. Preferably, R^1a and R^1b are independently of each other selected from hydrogen, halogen and Ci-C4-alkyl, more preferably from hydrogen and methyl, and are in particular hydrogen.

Z¹ is preferably selected from phenyl which may carry 1 , 2, 3, 4 or 5 radicals R^4a; and pyridyl which may carry 1 , 2 or 3 radicals R^4a. More preferably, Z¹ is selected from phenyl which may carry 1 , 2 or 3 radicals R^4a; and 2-pyridyl which may carry 1 , 2 or 3 radicals R^4a.

Z² is preferably selected from phenyl which may carry 1 , 2, 3, 4 or 5 radicals R^4b; and pyridyl which may carry 1 , 2 or 3 radicals R^4b. More preferably, Z² is selected from phenyl which may carry 1 , 2 or 3 radicals R^4b; and 2-pyridyl which may carry 1 , 2 or 3 radicals R^4b.

In Z¹ and Z², each R^4a and each R^4b is independently selected from halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, and in particular from halogen, methyl and trifluoromethoxy. Specifically R^4b is halogen; very specifically fluorine. In particular, Z¹ is selected from 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl,

3- bromophenyl, 4-bromophenyl, 3-chloro-4-fluorophenyl, 3-(trifluoromethyl)-phenyl,

4- (trifluoromethyl)-phenyl, 3-(trifluoromethoxy)-phenyl, 4-(trifluoromethoxy)-phenyl,

5- chloropyridin-2-yl, 5-bromopyridin-2-yl and 5-(trifluoromethyl)-pyridin-2-yl; and

Z² is selected from 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl 2,6-difluorophenyl, 3,4-difluorophenyl,

3,5-difluorophenyl and 2,4,6-trifluorophenyl.

R¹⁴ is preferably selected from hydrogen, halogen, cyano, nitro, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, amino, Ci-C6-alkylamino and di-(Ci-C6- alkyl)-amino, more preferably from hydrogen, halogen, cyano, Ci-C6-alkyl and C1-C6- haloalkyl, and is in particular hydrogen.

In the above radicals, preferably, each R¹⁶ is independently selected from halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, C1-C4- alkylsulfonyl, Ci-C4-haloalkylsulfonyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkylcarbonyl,

Ci-C4-haloalkylcarbonyl, aminocarbonyl, Ci-C4-alkylaminocarbonyl and di-(Ci-C4- alkyl)aminocarbonyl; more preferably from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl and Ci-C4-haloalkylsulfonyl, and in particular from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy. In a specific embodiment, the compounds of formula I are a compound of formula 1.1 or

where A, R^4a and R^4b have one of the above general, or in particular, one of the above preferred meanings, x and y are independentyl 0, 1 , 2 or 3, in particular 1 or 2, and Y is CH or N. In compounds 1.1 , A is preferably a group A1 or A2, and in particular

-CR^d=N-R^c1, -C(=N-N(R^c1)R^c2)R^d or -OR^a; and in compounds I.2 A is preferably a group A2 and in particular Ci-C6-alkyl, specifically Ci-C4-alkyl. Examples of preferred compounds are compounds of the following formulae la.1 to la.8 and the stereoisomers thereof, where R^4a, R^4b, R^a, R^c1 and A have one of the general or preferred meanings given above, Y is N or CH and x and y are independently 0, 1 , 2 or 3. Examples of preferred compounds are the individual compounds compiled in the tables 1 to 703 below. Moreover, the meanings mentioned below for the individual vari- ables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question. It has to be noticed that the below structures of formulae la.2 to la.7 are not to be understood to limit the stereochemistry at the C=N double bond of the imino or hydrazono group, but represent all stereoisomers (cis/trans isomers) and mixtures thereof.

Table 1

Compounds of the formula la.1 in which R^a is hydrogen, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 2

Compounds of the formula la.1 in which R^a is methyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 3

Compounds of the formula la.1 in which R^a is ethyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 4

Compounds of the formula la.1 in which R^a is n-propyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 5

Compounds of the formula la.1 in which R^a is isopropyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 6

Compounds of the formula la.1 in which R^a is n-butyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 7

Compounds of the formula la.1 in which R^a is sec-butyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 8

Compounds of the formula la.1 in which R^a is isobutyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 9

Compounds of the formula la.1 in which R^a is tert-butyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 10

Compounds of the formula la.1 in which R^a is CHF2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 1 1

Compounds of the formula la.1 in which R^a is CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 12

Compounds of the formula la.1 in which R^a is CH2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 13

Compounds of the formula la.1 in which R^a is CF2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 14

Compounds of the formula la.1 in which R^a is propen-1 -yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 15

Compounds of the formula la.1 in which R^a is propen-2-yl (allyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 16

Compounds of the formula la.1 in which R^a is propyn-2-yl (propargyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 17

Compounds of the formula la.1 in which R^a is phenyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 18

Compounds of the formula la.1 in which R^a is benzyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 19

Compounds of the formula la.1 in which R^a is cyclopropyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 20

Compounds of the formula la.1 in which R^a is cyclobutyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 21

Compounds of the formula la.1 in which R^a is cyclopentyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 22

Compounds of the formula la.1 in which R^a is cydohexyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 23

Compounds of the formula la.1 in which R^a is -C(=0)CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 24

Compounds of the formula la.1 in which R^a is -C(=0)CH2CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 25

Compounds of the formula la.1 in which R^a is -C(=0)CH2CH2CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 26

Compounds of the formula la.1 in which R^a is -C(=0)CH(CH3)2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 27

Compounds of the formula la.1 in which R^a is -C(=0)CH2CH2CH2CH3, and the combi- nation of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 28

Compounds of the formula la.1 in which R^a is -C(=0)CH2CH(CH3)2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Ta- ble A

Table 29

Compounds of the formula la.1 in which R^a is -C(=0)CH(CH₃)CH2CH₃, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 30

Compounds of the formula la.1 in which R^a is -C(=0)C(CH3)3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 31

Compounds of the formula la.2 in which R^c1 is methyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 32

Compounds of the formula la.2 in which R^c1 is ethyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 33

Compounds of the formula la.2 in which R^c1 is n-propyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 34

Compounds of the formula la.2 in which R^c1 is isopropyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 35

Compounds of the formula la.2 in which R^c1 is n-butyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 36

Compounds of the formula la.2 in which R^c1 is sec-butyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 37

Compounds of the formula la.2 in which R^c1 is isobutyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 38

Compounds of the formula la.2 in which R^c1 is tert-butyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 39

Compounds of the formula la.2 in which R^c1 is CHF2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 40

Compounds of the formula la.2 in which R^c1 is CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 41

Compounds of the formula la.2 in which R^c1 is CH2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 42

Compounds of the formula la.2 in which R^c1 is CF2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 43

Compounds of the formula la.2 in which R^c1 is propen-1 -yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 44

Compounds of the formula la.2 in which R^c1 is propen-2-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 45

Compounds of the formula la.2 in which R^c1 is propyn-2-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 46

Compounds of the formula la.2 in which R^c1 is cyclopropyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 47

Compounds of the formula la.2 in which R^c1 is cyclobutyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 48

Compounds of the formula la.2 in which R^c1 is cyclopentyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 49

Compounds of the formula la.2 in which R^c1 is cyclohexyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 50

Compounds of the formula la.2 in which R^c1 is phenyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 51

Compounds of the formula la.2 in which R^c1 is benzyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 52

Compounds of the formula la.2 in which R^c1 is pyridin-2-yl, and the combination of (R^4a)x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 53

Compounds of the formula la.2 in which R^c1 is pyridin-3-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 54

Compounds of the formula la.2 in which R^c1 is pyridin-4-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 55

Compounds of the formula la.2 in which R^c1 is OH, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 56

Compounds of the formula la.2 in which R^c1 is methoxy, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 57

Compounds of the formula la.2 in which R^c1 is ethoxy, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 58

Compounds of the formula la.2 in which R^c1 is n-propoxy, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 59

Compounds of the formula la.2 in which R^c1 is isopropoxy, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 60

Compounds of the formula la.2 in which R^c1 is n-butoxy, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 61

Compounds of the formula la.2 in which R^c1 is sec-butoxy, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 62

Compounds of the formula la.2 in which R^c1 is isobutoxy, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 63

Compounds of the formula la.2 in which R^c1 is tert-butoxy, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 64

Compounds of the formula la.2 in which R^c1 is -OCHF2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 65

Compounds of the formula la.2 in which R^c1 is -OCF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 66

Compounds of the formula la.2 in which R^c1 is -OCH2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 67

Compounds of the formula la.2 in which R^c1 is -OCF2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 68

Compounds of the formula la.2 in which R^c1 is -0-CH=CH2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 69

Compounds of the formula la.2 in which R^c1 is -0-CH=CH-CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 70

Compounds of the formula la.2 in which R^c1 is -0-CH2-CH=CH2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 71

Compounds of the formula la.2 in which R^c1 is -O-CH2-CC CH2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 72

Compounds of the formula la.2 in which R^c1 is -0-CH2-CH=CHCI, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 73

Compounds of the formula la.2 in which R^c1 is -O-CH2-CC CHCI, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 74

Compounds of the formula la.2 in which R^c1 is -0-CH2-C≡CH, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 75

Compounds of the formula la.2 in which R^c1 is -O-cyclopropyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 76

Compounds of the formula la.2 in which R^c1 is -O-cyclobutyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 77

Compounds of the formula la.2 in which R^c1 is -O-cyclopentyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 78

Compounds of the formula la.2 in which R^c1 is -O-cyclohexyl, and the combination of (R^4a)x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 79

Compounds of the formula la.2 in which R^c1 is -O-Chb-cyclopropyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 80

Compounds of the formula la.2 in which R^c1 is -O-Chb-cyclobutyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 81

Compounds of the formula la.2 in which R^c1 is -O-Chb-cyclopentyl, and the combina- tion of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 82

Compounds of the formula la.2 in which R^c1 is -O-Chb-cyclohexyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 83

Compounds of the formula la.2 in which R^c1 is phenoxy, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 84

Compounds of the formula la.2 in which R^c1 is benzyloxy, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 85

Compounds of the formula la.2 in which R^c1 is pyridin-2-yloxy, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 86

Compounds of the formula la.2 in which R^c1 is pyridin-3-yloxy, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 87

Compounds of the formula la.2 in which R^c1 is pyridin-4-yloxy, and the combination of (R^4a)x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 88

Compounds of the formula la.2 in which R^c1 is -0-CH2-(2-fluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 89

Compounds of the formula la.2 in which R^c1 is -0-CH2-(3-fluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 90

Compounds of the formula la.2 in which R^c1 is -0-CH2-(4-fluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 91

Compounds of the formula la.2 in which R^c1 is -0-CH2-(2,3-difluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 92

Compounds of the formula la.2 in which R^c1 is -0-CH2-(2,4-difluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 93

Compounds of the formula la.2 in which R^c1 is -0-CH2-(2,5-difluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 94

Compounds of the formula la.2 in which R^c1 is -0-CH2-(2,6-difluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 95

Compounds of the formula la.2 in which R^c1 is -0-CH2-(2,4,6-trifluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 96

Compounds of the formula la.2 in which R^c1 is -0-CH2-(3,4,5-trifluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 97

Compounds of the formula la.2 in which R^c1 is -0-CH2-(2-chlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 98

Compounds of the formula la.2 in which R^c1 is -0-CH2-(3-chlorophenyl), and the com- bination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 99

Compounds of the formula la.2 in which R^c1 is -0-CH2-(4-chlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 100

Compounds of the formula la.2 in which R^c1 is -0-CH2-(2,3-dichlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 101

Compounds of the formula la.2 in which R^c1 is -0-CH2-(2,4-dichlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 102

Compounds of the formula la.2 in which R^c1 is -0-CH2-(2,5-dichlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 103

Compounds of the formula la.2 in which R^c1 is -0-CH2-(2,6-dichlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 104

Compounds of the formula la.2 in which R^c1 is -0-CH2-(2,4,6-trichlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 105

Compounds of the formula la.2 in which R^c1 is -0-CH2-(3,4,5-trichlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 106

Compounds of the formula la.2 in which R^c1 is -0-CH2-(2-methylphenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 107

Compounds of the formula la.2 in which R^c1 is -0-CH2-(3-methylphenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 108

Compounds of the formula la.2 in which R^c1 is -0-CH2-(4-methylphenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 109

Compounds of the formula la.2 in which R^c1 is -0-CH2-pyridine-2-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 1 10

Compounds of the formula la.2 in which R^c1 is -0-CH2-pyridine-3-yl, and the combina- tion of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 1 1 1

Compounds of the formula la.2 in which R^c1 is -0-CH2-pyridine-4-yl, and the combina- tion of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 1 12

Compounds of the formula la.2 in which R^c1 is -0-CH2-(5-chloropyridine-2-yl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 1 13

Compounds of the formula la.2 in which R^c1 is -0-CH2-(6-chloropyridine-3-yl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 1 14

Compounds of the formula la.2 in which R^c1 is -O-ChbChb-phenyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 1 15

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(2-fluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 1 16

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(3-fluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 1 17

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(4-fluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 1 18

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(2,3-difluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 1 19

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(2,4-difluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 120

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(2,5-difluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 121

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(2,6-difluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 122

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(2,4,6-trifluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 123

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(3,4,5-trifluorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 124

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(2-chlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 125

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(3-chlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 126

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(4-chlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 127

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(2,3-dichlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 128

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(2,4-dichlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 129

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(2,5-dichlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 130

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(2,6-dichlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 131

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(2,4,6-trichlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 132

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(3,4,5-trichlorophenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 133

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(2-methylphenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 134

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(3-methylphenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 135

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(4-methylphenyl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 136

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-pyridine-2-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 137

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-pyridine-3-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 138

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-pyridine-4-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 139

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(5-chloropyridine-2-yl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 140

Compounds of the formula la.2 in which R^c1 is -0-CH2CH2-(6-chloropyridine-3-yl), and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Tables 141 to 250

Compounds of the formula la.3 in which R^c1 is as defined in tables 31 to 140, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 251

Compounds of the formula la.4 in which R^c1 is methyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 252

Compounds of the formula la.4 in which R^c1 is ethyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 253

Compounds of the formula la.4 in which R^c1 is n-propyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 254

Compounds of the formula la.4 in which R^c1 is isopropyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 255

Compounds of the formula la.4 in which R^c1 is n-butyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 256

Compounds of the formula la.4 in which R^c1 is sec-butyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 257

Compounds of the formula la.4 in which R^c1 is isobutyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 258

Compounds of the formula la.4 in which R^c1 is tert-butyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 259

Compounds of the formula la.4 in which R^c1 is CHF2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 260

Compounds of the formula la.4 in which R^c1 is CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 261

Compounds of the formula la.4 in which R^c1 is CH2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 262

Compounds of the formula la.4 in which R^c1 is CF2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 263

Compounds of the formula la.4 in which R^c1 is propen-1 -yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 264

Compounds of the formula la.4 in which R^c1 is propen-2-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 265

Compounds of the formula la.4 in which R^c1 is propyn-2-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 266

Compounds of the formula la.4 in which R^c1 is cyclopropyl, and the combination of (R^4a)x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 267

Compounds of the formula la.4 in which R^c1 is cyclobutyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 268

Compounds of the formula la.4 in which R^c1 is cyclopentyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 269

Compounds of the formula la.4 in which R^c1 is cyclohexyl, and the combination of

(R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 270

Compounds of the formula la.4 in which R^c1 is phenyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 271

Compounds of the formula la.4 in which R^c1 is benzyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 272

Compounds of the formula la.4 in which R^c1 is pyridine-2-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 273

Compounds of the formula la.4 in which R^c1 is pyridine-3-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 274

Compounds of the formula la.4 in which R^c1 is pyridine-4-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 275

Compounds of the formula la.4 in which R^c1 is -C(=0)CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 276

Compounds of the formula la.4 in which R^c1 is -C(=0)CH2CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 277

Compounds of the formula la.4 in which R^c1 is -C(=0)CH2CH2CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 278

Compounds of the formula la.4 in which R^c1 is -C(=0)CH(CH3)2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 279

Compounds of the formula la.4 in which R^c1 is -C(=0)CH2CH2CH2CH₃, and the combi- nation of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 280

Compounds of the formula la.4 in which R^c1 is -C(=0)CH(CH3)CH₂CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 281

Compounds of the formula la.4 in which R^c1 is -C(=0)CH2CH(CH3)2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 282

Compounds of the formula la.4 in which R^c1 is -C(=0)C(CH3)3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 283

Compounds of the formula la.4 in which R^c1 is -C(=0)CHF2, and the combination of (R^4a)x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 284

Compounds of the formula la.4 in which R^c1 is -C(=0)CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 285

Compounds of the formula la.4 in which R^c1 is -C(=0)CH2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 286

Compounds of the formula la.4 in which R^c1 is -C(=0)CF2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 287

Compounds of the formula la.4 in which R^c1 is -C(=0)NH2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 288

Compounds of the formula la.4 in which R^c1 is -C(=0)NHCH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 289

Compounds of the formula la.4 in which R^c1 is -C(=0)N(CH3)2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 290

Compounds of the formula la.4 in which R^c1 is -C(=0)NHCH2CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 291

Compounds of the formula la.4 in which R^c1 is -C(=0)N(CH₃)CH2CH₃, and the combi- nation of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 292

Compounds of the formula la.4 in which R^c1 is -C(=0)N(CH2CH3)2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 293

Compounds of the formula la.4 in which R^c1 is -C(=0)NHCH2CH₂CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 294

Compounds of the formula la.4 in which R^c1 is -C(=0)N(CH3)CH2CH₂CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 295

Compounds of the formula la.4 in which R^c1 is -C(=0)NHCH(CH3)2, and the combina- tion of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 296

Compounds of the formula la.4 in which R^c1 is -C(=0)NHCH2CH2CH₂CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 297

Compounds of the formula la.4 in which R^c1 is -C(=0)N(CH3)CH2CH2CH₂CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 298

Compounds of the formula la.4 in which R^c1 is -C(=0)NHCHF2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 299

Compounds of the formula la.4 in which R^c1 is -C(=0)NHCF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 300

Compounds of the formula la.4 in which R^c1 is -C(=0)NHCH2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 301

Compounds of the formula la.4 in which R^c1 is -C(=0)NHCF2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 302

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-propen-1 -yl, and the combi- nation of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 303

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-propen-2-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 304

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-propyn-2-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 305

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-cyclopropyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 306

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-cyclobutyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 307

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-cyclopentyl, and the combi- nation of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 308 Compounds of the formula la.4 in which R^c1 is -C(=0)NH-cyclohexyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 309

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-phenyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 310

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-benzyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 31 1

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-2-pyridyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 312

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-3-pyridyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 313

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-4-pyridyl, and the combina- tion of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 314

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-CH2-cyclopropyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 315

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-CH2-cyclobutyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 316

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-CH2-cyclopentyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 317

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-CH2-cyclohexyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 318 Compounds of the formula la.4 in which R^c1 is -C(=S)CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 319

Compounds of the formula la.4 in which R^c1 is -C(=S)CH2CH3, and the combination of (R^4a)x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 320

Compounds of the formula la.4 in which R^c1 is -C(=S)CH2CH2CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 321

Compounds of the formula la.4 in which R^c1 is -C(=S)CH(CH3)2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 322

Compounds of the formula la.4 in which R^c1 is -C(=S)CH2CH2CH2CH₃, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 323

Compounds of the formula la.4 in which R^c1 is -C(=S)CH(CH3)CH₂CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 324

Compounds of the formula la.4 in which R^c1 is -C(=S)CH2CH(CH3)2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 325

Compounds of the formula la.4 in which R^c1 is -C(=S)C(CH3)3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 326

Compounds of the formula la.4 in which R^c1 is -C(=S)CHF2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 327

Compounds of the formula la.4 in which R^c1 is -C(=S)CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 328

Compounds of the formula la.4 in which R^c1 is -C(=S)CH2CF3, and the combination of (R^4a)x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 329

Compounds of the formula la.4 in which R^c1 is -C(=S)CF2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 330 Compounds of the formula la.4 in which R^c1 is -C(=S)NH2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 331

Compounds of the formula la.4 in which R^c1 is -C(=S)NHCH3, and the combination of (R^4a)x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 332

Compounds of the formula la.4 in which R^c1 is -C(=S)N(CH3)2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 333

Compounds of the formula la.4 in which R^c1 is -C(=S)NHCH2CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 334

Compounds of the formula la.4 in which R^c1 is -C(=S)N(CH3)CH2CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Ta- ble A

Table 335

Compounds of the formula la.4 in which R^c1 is -C(=S)N(CH2CH3)2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 336

Compounds of the formula la.4 in which R^c1 is -C(=S)NHCH2CH₂CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 337

Compounds of the formula la.4 in which R^c1 is -C(=S)N(CH3)CH2CH₂CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 338

Compounds of the formula la.4 in which R^c1 is -C(=S)NHCH(CH3)2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Ta- ble A

Table 339

Compounds of the formula la.4 in which R^c1 is -C(=S)NHCH2CH2CH₂CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 340

Compounds of the formula la.4 in which R^c1 is -C(=S)N(CH3)CH2CH2CH₂CH3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 341 Compounds of the formula la.4 in which R^c1 is -C(=S)NHCHF2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 342

Compounds of the formula la.4 in which R^c1 is -C(=S)NHCF3, and the combination of (R^4a)x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 343

Compounds of the formula la.4 in which R^c1 is -C(=S)NHCH2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 344

Compounds of the formula la.4 in which R^c1 is -C(=S)NHCF2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 345

Compounds of the formula la.4 in which R^c1 is -C(=S)NH-propen-1 -yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 346

Compounds of the formula la.4 in which R^c1 is -C(=S)NH-propen-2-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 347

Compounds of the formula la.4 in which R^c1 is -C(=S)NH-propyn-2-yl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 348

Compounds of the formula la.4 in which R^c1 is -C(=S)NH-cyclopropyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 349

Compounds of the formula la.4 in which R^c1 is -C(=S)NH-cyclobutyl, and the combina- tion of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 350

Compounds of the formula la.4 in which R^c1 is -C(=S)NH-cyclopentyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Ta- ble A

Table 351

Compounds of the formula la.4 in which R^c1 is -C(=S)NH-cyclohexyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 352

Compounds of the formula la.4 in which R^c1 is -C(=S)NH-phenyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 353

Compounds of the formula la.4 in which R^c1 is -C(=S)NH-benzyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table 354

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-2-pyridyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Ta- ble A

Table 355

Table 356

Compounds of the formula la.4 in which R^c1 is -C(=0)NH-4-pyridyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 357

Compounds of the formula la.4 in which R^c1 is -C(=S)NH-CH2-cyclopropyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 358

Compounds of the formula la.4 in which R^c1 is -C(=S)NH-CH2-cyclobutyl, and the com- bination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 359

Compounds of the formula la.4 in which R^c1 is -C(=S)NH-CH2-cyclopentyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 360

Compounds of the formula la.4 in which R^c1 is -C(=S)NH-CH2-cyclohexyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Tables 361 to 470

Compounds of the formula la.5 in which R^c1 is as defined in tables 251 to 360, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Tables 471 to 580 Compounds of the formula la.6 in which R^c1 is as defined in tables 251 to 360, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Tables 581 to 690

Compounds of the formula la.7 in which R^c1 is as defined in tables 251 to 360, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 691

Compounds of the formula la.8 in which A is hydrogen, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 692

Compounds of the formula la.8 in which A is methyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 693

Compounds of the formula la.8 in which A is ethyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 694

Compounds of the formula la.8 in which A is n-propyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 695

Compounds of the formula la.8 in which A is isopropyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 696

Compounds of the formula la.8 in which A is n-butyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 697

Compounds of the formula la.8 in which A is sec-butyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 698

Compounds of the formula la.8 in which A is isobutyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 699

Compounds of the formula la.8 in which A is tert-butyl, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 700

Compounds of the formula la.8 in which A is CHF2, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 701 Compounds of the formula la.8 in which A is CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 702

Compounds of the formula la.8 in which A is CH2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A

Table 703

Compounds of the formula la.8 in which A is CF2CF3, and the combination of (R^4a)_x, (R^4b)_y and Y for a compound corresponds in each case to one row of Table A Table A

No. (R^4a)x (R^4b)y Y No. (R^4a)x (R^4b)y Y

A-1 H H CH A-27 3-CFs H CH

A-2 2-F H CH A-28 4-CFs H CH

A-3 3-F H CH A-29 2-OCFs H CH

A-4 4-F H CH A-30 3-OCF3 H CH

A-5 2,3-F₂ H CH A-31 4-OCF3 H CH

A-6 2,4-F₂ H CH A-32 H 2-F CH

A-7 2,5-F₂ H CH A-33 2-F 2-F CH

A-8 2,6-F₂ H CH A-34 3-F 2-F CH

A-9 3,4-F₂ H CH A-35 4-F 2-F CH

A-10 3,5-F₂ H CH A-36 2,3-F₂ 2-F CH

A-1 1 2,4,6-Fs H CH A-37 2,4-F₂ 2-F CH

A-12 3,4,5-Fs H CH A-38 2,5-F₂ 2-F CH

A-13 2-CI H CH A-39 2,6-F₂ 2-F CH

A-14 3-CI H CH A-40 3,4-F₂ 2-F CH

A-15 4-CI H CH A-41 3,5-F₂ 2-F CH

A-16 2,3-CI₂ H CH A-42 2,4,6-Fs 2-F CH

A-17 2,4-CI₂ H CH A-43 3,4,5-Fs 2-F CH

A-18 2,5-CI₂ H CH A-44 2-CI 2-F CH

A-19 2,6-CI₂ H CH A-45 3-CI 2-F CH

A-20 3,4-CI₂ H CH A-46 4-CI 2-F CH

A-21 3,5-CI₂ H CH A-47 2,3-CI₂ 2-F CH

A-22 2,4,6-Cls H CH A-48 2,4-CI₂ 2-F CH

A-23 3,4,5-Cls H CH A-49 2,5-CI₂ 2-F CH

A-24 3-CI-4-F H CH A-50 2,6-CI₂ 2-F CH

A-25 4-CI-3-F H CH A-51 3,4-CI₂ 2-F CH

A-26 2-CFs H CH A-52 3,5-CI₂ 2-F CH No. (R^4a)x (R^4b)y Y No. (R^4a)x (R^4b)y Y

A-53 2,4,6-Cls 2-F CH A-90 4-CFs 4-F CH

A-54 3,4,5-Cls 2-F CH A-91 2-OCF3 4-F CH

A-55 3-CI-4-F 2-F CH A-92 3-OCF3 4-F CH

A-56 4-CI-3-F 2-F CH A-93 4-OCF3 4-F CH

A-57 2-CFs 2-F CH A-94 H 2,4-F₂ CH

A-58 3-CFs 2-F CH A-95 2-F 2,4-F₂ CH

A-59 4-CFs 2-F CH A-96 3-F 2,4-F₂ CH

A-60 2-OCFs 2-F CH A-97 4-F 2,4-F₂ CH

A-61 3-OCF3 2-F CH A-98 2,3-F₂ 2,4-F₂ CH

A-62 4-OCF3 2-F CH A-99 2,4-F₂ 2,4-F₂ CH

A-63 H 4-F CH A-100 2,5-F₂ 2,4-F₂ CH

A-64 2-F 4-F CH A-101 2,6-F₂ 2,4-F₂ CH

A-65 3-F 4-F CH A-102 3,4-F₂ 2,4-F₂ CH

A-66 4-F 4-F CH A-103 3,5-F₂ 2,4-F₂ CH

A-67 2,3-F₂ 4-F CH A-104 2,4,6-F₃ 2,4-F₂ CH

A-68 2,4-F₂ 4-F CH A-105 3,4,5-F₃ 2,4-F₂ CH

A-69 2,5-F₂ 4-F CH A-106 2-CI 2,4-F₂ CH

A-70 2,6-F₂ 4-F CH A-107 3-CI 2,4-F₂ CH

A-71 3,4-F₂ 4-F CH A-108 4-CI 2,4-F₂ CH

A-72 3,5-F₂ 4-F CH A-109 2,3-CI₂ 2,4-F₂ CH

A-73 2,4,6-F₃ 4-F CH A-1 10 2,4-CI₂ 2,4-F₂ CH

A-74 3,4,5-F₃ 4-F CH A-1 1 1 2,5-CI₂ 2,4-F₂ CH

A-75 2-CI 4-F CH A-1 12 2,6-CI₂ 2,4-F₂ CH

A-76 3-CI 4-F CH A-1 13 3,4-CI₂ 2,4-F₂ CH

A-77 4-CI 4-F CH A-1 14 3,5-CI₂ 2,4-F₂ CH

A-78 2,3-CI₂ 4-F CH A-1 15 2,4,6-CI₃ 2,4-F₂ CH

A-79 2,4-CI₂ 4-F CH A-1 16 3,4,5-CI₃ 2,4-F₂ CH

A-80 2,5-CI₂ 4-F CH A-1 17 3-CI-4-F 2,4-F₂ CH

A-81 2,6-CI₂ 4-F CH A-1 18 4-CI-3-F 2,4-F₂ CH

A-82 3,4-CI₂ 4-F CH A-1 19 2-CFs 2,4-F₂ CH

A-83 3,5-CI₂ 4-F CH A-120 3-CFs 2,4-F₂ CH

A-84 2,4,6-CI₃ 4-F CH A-121 4-CFs 2,4-F₂ CH

A-85 3,4,5-CI₃ 4-F CH A-122 2-OCFs 2,4-F₂ CH

A-86 3-CI-4-F 4-F CH A-123 3-OCF3 2,4-F₂ CH

A-87 4-CI-3-F 4-F CH A-124 4-OCF3 2,4-F₂ CH

A-88 2-CFs 4-F CH A-125 H H N

A-89 3-CFs 4-F CH A-126 3-F H N No. (R^4a)x (R^4b)y Y No. (R^4a)x (R^4b)y Y

A-127 4-F H N A-160 3-F 4-F N

A-128 5-F H N A-161 4-F 4-F N

A-129 6-F H N A-162 5-F 4-F N

A-130 3-CI H N A-163 6-F 4-F N

A-131 4-CI H N A-164 3-CI 4-F N

A-132 5-CI H N A-165 4-CI 4-F N

A-133 6-CI H N A-166 5-CI 4-F N

A-134 3-CFs H N A-167 6-CI 4-F N

A-135 4-CFs H N A-168 3-CFs 4-F N

A-136 5-CFs H N A-169 4-CFs 4-F N

A-137 6-CF3 H N A-170 5-CFs 4-F N

A-138 3-OCF3 H N A-171 6-CF3 4-F N

A-139 4-OCF3 H N A-172 3-OCF3 4-F N

A-140 5-OCF3 H N A-173 4-OCF3 4-F N

A-141 6-OCF3 H N A-174 5-OCF3 4-F N

A-142 H 2-F N A-175 6-OCF3 4-F N

A-143 3-F 2-F N A-176 H 2,4-F₂ N

A-144 4-F 2-F N A-177 3-F 2,4-F₂ N

A-145 5-F 2-F N A-178 4-F 2,4-F₂ N

A-146 6-F 2-F N A-179 5-F 2,4-F₂ N

A-147 3-CI 2-F N A-180 6-F 2,4-F₂ N

A-148 4-CI 2-F N A-181 3-CI 2,4-F₂ N

A-149 5-CI 2-F N A-182 4-CI 2,4-F₂ N

A-150 6-CI 2-F N A-183 5-CI 2,4-F₂ N

A-151 3-CFs 2-F N A-184 6-CI 2,4-F₂ N

A-152 4-CFs 2-F N A-185 3-CFs 2,4-F₂ N

A-153 5-CFs 2-F N A-186 4-CFs 2,4-F₂ N

A-154 6-CF3 2-F N A-187 5-CFs 2,4-F₂ N

A-155 3-OCF3 2-F N A-188 6-CF3 2,4-F₂ N

A-156 4-OCF3 2-F N A-189 3-OCF3 2,4-F₂ N

A-157 5-OCF3 2-F N A-190 4-OCF3 2,4-F₂ N

A-158 6-OCF3 2-F N A-191 5-OCF3 2,4-F₂ N

A-159 H 4-F N A-192 6-OCF3 2,4-F₂ N

If in table A (R^4a)_x or (R^4b)_y are defined to be H, this means that x or y are 0 and the phenyl/pyridyl rings carry no substituent R^4a or R^4b. The binding positions of the x radical(s) R^4a and of the y radical(s) R^4b are as follows (# being the attachment point of the phenyl or 2-pyridyl ring Z¹ and the phenyl ring Z² to the pyrazole ring):

4 5

Among the above compounds, preference is given to compounds of formula la.1 , la.2 and la.4.

In a specific embodiment, the invention relates to compounds I selected from the com- pounds of the examples, either in form of free bases or of any agriculturally acceptable salt thereof, or a steroisomer, the racemate or any mixture of stereoisomers thereof or the N-oxides or the tautomers thereof.

Compounds of formula I can be synthesized in analogy to methods described in WO 2013/061948. Scheme 1 shows the last step, which is a coupling reaction of a compound of formula II (with Y being a leaving group such as halogen or -OS02CH3, -OSO2CF3, -OSO2-P-C6H4-CH3 and the like) and a Q-H ring (H being bound to the nitrogen ring atom that forms the attachment point of the respective formula Q-1 , Q-2, Q-3 or Q-4 to CR^1aR^1b). Suitable reaction conditions for such a conversion are described for example in WO 2013/061948 or by Lee et al. Journal of Medicinal Chemistry 2008, 51 (22), 7216-7233.

Scheme 1

Compounds of formula II can be prepared by methods described in WO 2013/061948.

Alternatively, compounds of formula I can be prepared by reductive amination of a compound of formula III with the Q-H ring as shown in scheme 2. Methods describing such a conversion are described for example by Li et al., Bioorganic & Medicinal Chemistry Letters 2010, 20(16), 4932-4935.

The synthesis of the Q-1 -H radical of formula VII wherein X is CR^3e, L is a bond and A is OR^a as shown in scheme 3 is starting with a hydroxypiperidine of formula IV.

Protection of the compound of formula IV with a suitable protecting group (PG), as for example described in WO 2004/009550 or US 6,362,188, leads to a compound of formula V which subsequently is either alkylated or acylated at the hydroxy moiety, as described for example in US 2003/236250, WO 2006/104406 or US 201 1/92475, to form a compound of formula VI. Deprotection as described for example in

WO 2006/64196, WO 2004/104001 or US 201 1/92475 leads to compounds of formula VII. Starting compound of formula IV can be synthesized from the respective hydroxypyridines, as described for example by Hall et al. Journal of the American Chemical Society 1958, 80, 6412-6419. Alternatively, compounds of formula IV can be synthesized from 1 ,3-dicyano-propane-2-ol under hydrogenation conditions, as described for example by Bowden et al. Journal of the Chemical Society 1952, 1 164- 1 166.

Scheme 3

(VI) (VII)

Q-1 radicals of the formula XIV wherein X is CR^3e and L-A is a -CR^d=N-R^c1 or other members of the family A1 can be introduced, for example, as shown in scheme 4. Pro- tection (PG is a protecting group) of compounds of formula VIII as described for example by Ting et al. Bioorganic and Medicinal Chemistry Letters 2001 , 1 1 (4), 491 -494 gives compounds of formula IX. Oxidation of the latter as described for example by Ting et al. Bioorganic and Medicinal Chemistry Letters 2001 , 1 1 (4), 491 -494 or in US 2008/300242 leads to compounds of formula X. Introduction of an R^d radical can be accomplished by the addition of an organometallic reagent as for example described in WO 2012/092827, WO 2005/026145 or WO 2012/018668 to yield compounds of formula XI. Oxidation of the latter in analogy to the methods as described for example by Ting et al. Bioorganic and Medicinal Chemistry Letters 2001 , 1 1 (4), 491 -494 leads to compounds of formula XII. Amination of compounds of formula XII as described for example in WO 2008/1 18718 gives compounds of formula XIII. Similarly, compounds of formula X may be subjected to the same conditions to give compounds of formula XIII with R^d = H. Deprotection of compounds of formula XIII as for example described by Ivobe et al. Chemical & Pharmaceutical Bulletin, 2001 , 49(7), 822-829 leads to compounds of formula XIV. Starting compound of formula IV can be synthesized from the respective hydroxymethylpyridines by hydrogenation as for example described in US 2003/55244.

Scheme 4

Q-1 -radicals of the formula XVIII wherein X is N and L-A is a -CR^d=N-R^c1 or other members of the family A1 can be introduced as shown in scheme 5. Piperazine com- pounds of formula XV are protected as described for example by Kunieda et al. Tetrahedron Letters 1982, 23(1 1 ), 1 159-1 160. Introduction of an isocyanate as described for example in WO 2007/056170 leads to compounds of formula XVII (with R^d = H) which leads to compounds of formula XVIII upon deprotection, as described for example in WO 2007/056170. Compounds of formula XVII where R^d is not hydrogen can be prepared as described for example in WO 2003/103661 , Areschka et al. European Journal of Medicinal Chemistry 1976, 1 1 (2), 125-131 , Macit et al. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry 1998, 28(5), 833-841 , US 2007/0173495 or Moreau et al. European Journal of Medicinal Chemistry 1977, 12(4), 365-9.

Scheme 5

(XV) (XVI)

(XVII) (XVIII)

Q-2 radicals of the formula XXII can be introduced as shown in scheme 6. Piperidi- nones of formula XIX are protected at the N-terminus as described for example by Bridges et al. Bioorganic & Medicinal Chemistry Letters 2008, 18(20), 5439-5442 to give compounds of formula XX. Introduction of the B-moiety, followed by deprotection yields compounds of formula XXI and XXII, respectively. Transformation into B = S can be done by reaction with Lawesson's reagent as described for example in

WO 2012/051 1 17. Conversion into B = CR^d1R^d2 can be carried out as described for example in US 2005/0261322. Conversion into B = NR^c1 can be carried out as described for example by Xu et al. Bioorganic & Medicinal Chemistry Letters 2010, 20(9), 2942- 2945. Deprotection can be achieved by using standard procedures as described for example in WO 2007/056170.

Scheme 6

(XXI) (XXII)

Q-3 radicals of the formula XXVII can be introduced as shown in scheme 7 from thio- morpholinones of formula XXIII by protection of compounds XXIII as described for ex- ample in WO 2008/083038 or in WO 99/09027 to give compounds of formula XXIV. Conversion into compounds of formula XXV, XXVI and XXVII can be carried out by methods as described in WO 201 1/029537.

Scheme 7

(XXV) (XXVI)

(XXVII)

Compounds of formula I carrying a radical Q-4 (below termed XXIX) can be prepared as shown in scheme 8 from compounds of formula II as described for example by D'Auria et al. European Journal of Organic Chemistry 2009, (6), 932-937 by reacting the derived azide of formula XXVIII with an olefin.

Scheme 8

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 Acronicta major, Adoxophyes orana, Aedia leucomelas, Agrotis spp. such as Agrotis fucosa, Agrotis segetum, Agrotis ypsilon; Alabama argillacea, Anticarsia gemmatalis, Anticarsia spp., Argyresthia conjugella, Autographa gamma, Barathra brassicae, Bucculatrix thurberiel- la, Bupalus piniarius, Cacoecia murinana, Cacoecia podana, Capua reticulana, Car- pocapsa pomonella, Cheimatobia brumata, Chilo spp. such as Chilo suppressalis; Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Clysia am- biguella, Cnaphalocerus spp., Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Ephestia cautella, Ephestia kuehniella, Eupoecilia ambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bouliana, Feltia spp. such as Feltia subterranean; Galleria mellonella, Grapho- litha funebrana, Grapholitha molesta, Helicoverpa spp. such as Helicoverpa armigera, Helicoverpa zea; Heliothis spp. such as Heliothis armigera, Heliothis virescens, Helio- this zea; Hellula undalis, Hibernia defoliaria, Hofmannophila pseudospretella, Homona magnanima, Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus,

Keiferia lycopersicella, Lambdina fiscellaria, Laphygma spp. such as Laphygma exigua; Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lithophane anten- nata, Lobesia botrana, Loxagrotis albicosta, Loxostege sticticalis, Lymantria spp. such as Lymantria dispar, Lymantria monacha; Lyonetia clerkella, Malacosoma neustria, Mamestra spp. such as Mamestra brassicae; Mocis repanda, Mythimna separata, Or- gyia pseudotsugata, Oria spp., Ostrinia spp. such as Ostrinia nubilalis; Oulema oryzae, Panolis flammea, Pectinophora spp. such as Pectinophora gossypiella; Peridroma saucia, Phalera bucephala, Phthorimaea spp. such as Phthorimaea operculella; Phyl- locnistis citrella, Pieris spp. such as Pieris brassicae, Pieris rapae; Plathypena scabra, Plutella maculipennis, Plutella xylostella, Prodenia spp., Pseudaletia spp., Pseudoplu- sia includens, Pyrausta nubilalis, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotro- ga cerealella, Sparganothis pilleriana, Spodoptera spp. such as Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura; Thaumatopoea pityocampa, Thermesia gem- matalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp. such as Trichoplusia ni; Tuta absoluta, and Zeiraphera canadensis, beetles (Coleoptera), for example Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agrilus sinuatus, Agriotes spp. such as Agriotes fuscicollis, Agriotes lineatus, Agri- otes obscurus; Amphimallus solstitialis, Anisandrus dispar, Anobium punctatum, Anomala rufocuprea, Anoplophora spp. such as Anoplophora glabripennis; Anthono- mus spp. such as Anthonomus grandis, Anthonomus pomorum; Anthrenus spp., Aph- thona euphoridae, Apogonia spp., Athous haemorrhoidalis, Atomaria spp. such as Atomaria linearis; Attagenus spp., Aulacophora femoralis, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as Bruchus lentis, Bruchus pisorum, Bruchus rufimanus; Byctiscus betulae, Callosobruchus chinensis, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorhynchus spp. such as Ceuthor- rhynchus assimilis, Ceuthorrhynchus napi; Chaetocnema tibialis, Cleonus mendicus, Conoderus spp. such as Conoderus vespertinus; Cosmopolites spp., Costelytra zea- landica, Crioceris asparagi, Cryptorhynchus lapathi, Ctenicera ssp. such as Ctenicera destructor; Curculio spp., Dectes texanus, Dermestes spp., Diabrotica spp. such as Diabrotica 12-punctata Diabrotica speciosa, Diabrotica longicornis, Diabrotica semi- punctata, Diabrotica virgifera; Epilachna spp. such as Epilachna varivestis, Epilachna vigintioctomaculata; Epitrix spp. such as Epitrix hirtipennis; Eutinobothrus brasiliensis, Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hy- lobius abietis, Hylotrupes bajulus, Hypera brunneipennis, Hypera postica, Hypothene- mus spp., Ips typographus, Lachnosterna consanguinea, Lema bilineata, Lema mela- nopus, Leptinotarsa spp. such as Leptinotarsa decemlineata; Limonius californicus, Lissorhoptrus oryzophilus, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp. such as Lyctus bruneus; Melanotus communis, Meligethes spp. such as Meligethes aeneus; Melolontha hippocastani, Melolontha melolontha, Migdolus spp., Monochamus spp. such as Monochamus alternatus; Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochle- ariae, Phyllobius pyri, Phyllopertha horticola, Phyllophaga spp., Phyllotreta spp. such as Phyllotreta chrysocephala, Phyllotreta nemorum, Phyllotreta striolata; Phyllophaga spp., Phyllopertha horticola, Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinus spp., Rhizobius ventralis , Rhizopertha dominica, Sitona lineatus, Sitophilus spp. such as Sitophilus granaria, Sitophilus zeamais; Sphenophorus spp. such as Sphenophorus levis; Sternechus spp. such as Sternechus subsignatus; Sym- phyletes spp., Tenebrio molitor, Tribolium spp. such as Tribolium castaneum; Tro- goderma spp., Tychius spp., Xylotrechus spp., and Zabrus spp. such as Zabrus teneb- rioides, flies, mosquitoes (Diptera), e.g. Aedes spp. such as Aedes aegypti, Aedes albopictus, Aedes vexans; Anastrepha ludens, Anopheles spp. such as Anopheles albimanus, Anopheles crucians, Anopheles freeborni, Anopheles gambiae, Anopheles leucosphy- rus, Anopheles maculipennis, Anopheles minimus, Anopheles quadrimaculatus, Anopheles sinensis; Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Cerafitis capitata, Ceratitis capitata, Chrysomyia spp. such as Chrysomya bezziana,

Chrysomya hominivorax, Chrysomya macellaria; Chrysops atlanticus, Chrysops discal- is, Chrysops silacea, Cochliomyia spp. such as Cochliomyia hominivorax; Contarinia spp. such as Contarinia sorghicola; Cordylobia anthropophaga, Culex spp. such as Culex nigripalpus, Culex pipiens, Culex quinquefasciatus, Culex tarsalis, Culex tri- taeniorhynchus; Culicoides furens, Culiseta inornata, Culiseta melanura, Cuterebra spp., Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia spp. such as Delia antique, Delia coarctata, Delia platura, Delia radicum; Dermatobia hominis, Drosophila spp., Fannia spp. such as Fannia canicularis; Gastraphilus spp. such as Gasterophilus intestinalis; Geomyza Tripunctata, Glossina fuscipes, Glossina morsitans, Glossina palpalis, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia spp. such as Hylemyia platura; Hypoderma spp. such as Hypoderma lineata; Hyppobosca spp., Leptoconops torrens, Liriomyza spp. such as Liriomyza sati- vae, Liriomyza trifolii; Lucilia spp. such as Lucilia caprina, Lucilia cuprina, Lucilia serica- ta; Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. such as Mayetiola destructor; Musca spp. such as Musca autumnalis, Musca domestica; Muscina stabulans, Oestrus spp. such as Oestrus ovis; Opomyza florum, Oscinella spp. such as Oscinella frit; Pe- gomya hysocyami, Phlebotomus argentipes, Phorbia spp. such as Phorbia antiqua, Phorbia brassicae, Phorbia coarctata; Prosimulium mixtum, Psila rosae, Psorophora columbiae, Psorophora discolor, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga spp. such as Sarcophaga haemorrhoidalis; Simulium vittatum, Stomoxys spp. such as Stomoxys calcitrans; Tabanus spp. such as Tabanus atratus, Tabanus bovinus, Taba- nus lineola, Tabanus similis; Tannia spp., Tipula oleracea, Tipula paludosa, and Wohlfahrtia spp., thrips (Thysanoptera), e.g. Baliothrips biformis, Dichromothrips corbetti, Dichromothrips ssp., Enneothrips flavens, Frankliniella spp. such as Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici; Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp. such as Scirtothrips citri; Taeni- othrips cardamoni, Thrips spp. such as Thrips oryzae, Thrips palmi, Thrips tabaci; termites (Isoptera), e.g. Calotermes flavicollis, Coptotermes formosanus, Heterotermes aureus, Heterotermes longiceps, Heterotermes tenuis, Leucotermes flavipes, Odonto- termes spp., Reticulitermes spp. such as Reticulitermes speratus, Reticulitermes fla- vipes, Reticulitermes grassei, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes virginicus; Termes natalensis, cockroaches (Blattaria - Blattodea), e.g. Acheta domesticus, Blatta orientalis, Blattella asahinae, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Periplaneta australasiae, Periplaneta brun- nea, Periplaneta fuligginosa, Periplaneta japonica, bugs, aphids, leafhoppers, whiteflies, scale insects, cicadas (Hemiptera), e.g. Acros- ternum spp. such as Acrosternum hilare; Acyrthosipon spp. such as Acyrthosiphon onobrychis, Acyrthosiphon pisum; Adelges laricis, Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anasa tris- tis, Antestiopsis spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphidula nasturtii, Aphis spp. such as Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis grossu- lariae, Aphis pomi, Aphis sambuci, Aphis schneideri, Aphis spiraecola; Arboridia apica- lis, Arilus critatus, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp. such as Bemisia argentifolii, Bemisia tabaci; Blissus spp. such as Blissus leucopterus; Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brachycolus spp., Brevicoryne brassicae, Calligypona margi- nata, Calocoris spp., Campylomma livida, Capitophorus horni, Carneocephala fulgida, Cavelerius spp., Ceraplastes spp., Ceratovacuna lanigera, Cercopidae, Cerosipha gossypii, Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Cimex spp. such as Cimex he- mipterus, Cimex lectularius; Coccomytilus halli, Coccus spp., Creontiades dilutus, Cryptomyzus ribis, Cryptomyzus ribis, Cyrtopeltis notatus, Dalbulus spp., Dasynus pi- peris, Dialeurades spp., Diaphorina spp., Diaspis spp., Dichelops furcatus, Diconocoris hewetti, Doralis spp., Dreyfusia nordmannianae, Dreyfusia piceae, Drosicha spp., Dysaphis spp. such as Dysaphis plantaginea, Dysaphis pyri, Dysaphis radicola; Dysau- lacorthum pseudosolani, Dysdercus spp. such as Dysdercus cingulatus, Dysdercus intermedius; Dysmicoccus spp., Empoasca spp. such as Empoasca fabae, Empoasca solana; Eriosoma spp., Erythroneura spp., Eurygaster spp. such as Eurygaster integri- ceps; Euscelis bilobatus, Euschistus spp. such as Euschistuos heros, Euschistus im- pictiventris, Euschistus servus; Geococcus coffeae, Halyomorpha spp. such as Halyo- morpha halys; Heliopeltis spp., Homalodisca coagulata, Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lactucae, lcerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Leptocorisa spp., Leptoglossus phyl- lopus, Lipaphis erysimi, Lygus spp. such as Lygus hesperus, Lygus lineolaris, Lygus pratensis; Macropes excavatus, Macrosiphum spp. such as Macrosiphum rosae, Ma- crosiphum avenae, Macrosiphum euphorbiae; Mahanarva fimbriolata, Megacopta cri- braria, Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari, Metcafiella spp.,

Metopolophium dirhodum, Miridae spp., Monellia costalis, Monelliopsis pecanis, Myzus spp. such as Myzus ascalonicus, Myzus cerasi, Myzus persicae, Myzus varians; Naso- novia ribis-nigri, Nephotettix spp. such as Nephotettix malayanus, Nephotettix nigropic- tus, Nephotettix parvus, Nephotettix virescens; Nezara spp. such as Nezara viridula; Nilaparvata lugens, Oebalus spp., Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp. such as Pemphigus bur- sarius; Pentomidae, Peregrinus maidis, Perkinsiella saccharicida, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Piesma quadrata, Piezodo- rus spp. such as Piezodorus guildinii, Pinnaspis aspidistrae, Planococcus spp., Proto- pulvinaria pyriformis, Psallus seriatus, Pseudacysta persea, Pseudaulacaspis pentago- na, Pseudococcus spp. such as Pseudococcus comstocki; Psylla spp. such as Psylla mali, Psylla piri; Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Reduvius senilis, Rhodnius spp., Rhopalomyzus ascalonicus, Rho- palosiphum spp. such as Rhopalosiphum pseudobrassicas, Rhopalosiphum insertum, Rhopalosiphum maidis, Rhopalosiphum padi; Sagatodes spp., Sahlbergella singularis, Saissetia spp., Sappaphis mala, Sappaphis mali, Scaphoides titanus, Schizaphis gra- minum, Schizoneura lanuginosa, Scotinophora spp., Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Solubea insularis , Stephanitis nashi, Sticto- cephala festina, Tenalaphara malayensis, Thyanta spp. such as Thyanta perditor; Ti- braca spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp. such as Toxoptera aurantii; Trialeurodes spp. such as Trialeurodes vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. such as Unaspis yanonensis; and Viteus vitifolii, ants, bees, wasps, sawflies (Hymenoptera), e.g. Athalia rosae, Atta capiguara, Atta cephalotes, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Bombus spp., Camponotus floridanus, Crematogaster spp., Dasymutilla occidentalis, Diprion spp., Dolichovespula maculata, Hoplocampa spp. such as Hoplocampa minuta, Hoplocampa testudinea; Lasius spp. such as Lasius niger, Linepithema humile, Mono- morium pharaonis, Paravespula germanica, Paravespula pennsylvanica, Paravespula vulgaris, Pheidole megacephala, Pogonomyrmex barbatus, Pogonomyrmex californi- cus, Polistes rubiginosa, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Vespa spp. such as Vespa crabro, and Vespula squamosa, crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica, Calliptamus itali- cus, Chortoicetes terminifera, Dociostaurus maroccanus, Gryllotalpa africana, Gryllo- talpa gryllotalpa, Hieroglyphus daganensis, Kraussaria angulifera, Locusta migratoria, Locustana pardalina, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Oedaleus senegalensis, Schistocerca americana, Schistocerca gregaria, Tachycines asynamorus, and Zonozerus variegatus, arachnids (Arachnida), such as acari,e.g. of the families Argasidae, Ixodidae and Sar- coptidae, such as Amblyomma spp. (e.g. Amblyomma americanum, Amblyomma var- iegatum, Amblyomma maculatum), Argas spp. (e.g. Argas persicus), Boophilus spp. (e.g. Boophilus annulatus, Boophilus decoloratus, Boophilus microplus), Dermacentor silvarum, Dermacentor andersoni, Dermacentor variabilis, Hyalomma spp. (e.g. Hy- alomma truncatum), Ixodes spp. (e.g. Ixodes ricinus, Ixodes rubicundus, Ixodes scapu- laris, Ixodes holocyclus, Ixodes pacificus), Ornithodorus spp. (e.g. Ornithodorus mou- bata, Ornithodorus hermsi, Ornithodorus turicata), Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes spp. (e.g. Psoroptes ovis), Rhipicephalus spp. (e.g. Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus evertsi), Rhizoglyphus spp., Sarcoptes spp. (e.g. Sarcoptes scabiei), and Eriophyidae spp. such as Acaria sheldoni, Aculops spp. (e.g. Aculops pelekassi) Aculus spp. (e.g. Aculus schlechtendali), Epitrimerus pyri, Phyllocoptruta oleivora and Eriophyes spp. (e.g. Eriophyes sheldoni); Tarsonemidae spp. such as Hemitarsonemus spp., Phy- tonemus pallidus and Polyphagotarsonemus latus, Stenotarsonemus spp.; Tenuipalpi- dae spp. such as Brevipalpus spp. (e.g. Brevipalpus phoenicis); Tetranychidae spp. such as Eotetranychus spp., Eutetranychus spp., Oligonychus spp., Tetranychus cin- nabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae; Bryobia praetiosa, Panonychus spp. (e.g. Panonychus ulmi, Panonychus citri), Metatetranychus spp. and Oligonychus spp. (e.g. Oligonychus pratensis), Vasates lycopersici; Araneida, e.g. Latrodectus mactans, and Loxosceles reclusa. And Acarus siro, Chorioptes spp., Scorpio maurus, fleas (Siphonaptera), e.g. Ceratophyllus spp., 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. Geophilus spp., Scutigera spp. such as Scutigera coleop- trata; millipedes (Diplopoda), e.g. Blaniulus guttulatus, Narceus spp., Earwigs (Dermaptera), e.g. forficula auricularia, lice (Phthiraptera), e.g. Damalinia spp., Pediculus spp. such as Pediculus humanus capitis, Pediculus humanus corporis; Pthirus pubis, Haematopinus spp. such as Hae- matopinus eurysternus, Haematopinus suis; Linognathus spp. such as Linognathus vituli; Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp., springtails (Collembola ), e.g. Onychiurus ssp. such as Onychiurus armatus.

They are also suitable for controlling nematodes: plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javani- ca, 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, An- guina species; Stem and foliar nematodes, Aphelenchoides species such as Aphelen- choides besseyi ; Sting nematodes, Belonolaimus longicaudatus and other Belono- laimus species; Pine nematodes, Bursaphelenchus lignicolus Mamiya et Kiyohara, 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 Lon- gidorus species; Lesion nematodes, Pratylenchus brachyurus, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other

Radopholus species; Reniform nematodes, Rotylenchus robustus, Rotylenchus reni- formis 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 Tylencho- rhynchus species; Citrus nematodes, Tylenchulus species such as Tylenchulus semi- penetrans; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species. Examples of further pest species which may be controlled by compounds of fomula (I) include: from the class of the Bivalva, for example, Dreissena spp.; from the class of the Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.; from the class of the helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus me- dinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicu- laris, Faciola spp., Haemonchus spp. such as Haemonchus contortus; Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagosto- mum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercora lis, Strony- loides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti; from the order of the Isopoda, for example,

Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of the Symphy- la, for example, Scutigerella immaculata;

Further examples of pest species which may be controlled by compounds of formula (I) include: Anisoplia austriaca, Apamea spp., Austroasca viridigrisea, Baliothrips biformis, Caenorhabditis elegans, Cephus spp., Ceutorhynchus napi, Chaetocnema aridula, Chilo auricilius, Chilo indicus , Chilo polychrysus, Chortiocetes terminifera, Cnaphalo- croci medinalis, Cnaphalocrosis spp., Colias eurytheme, Collops spp., Cornitermes cumulans, Creontiades spp., Cyclocephala spp., Dalbulus maidis, Deraceras reticula- turn , Diatrea saccharalis, Dichelops furcatus, Dicladispa armigera , Diloboderus spp. such as Diloboderus abderus; Edessa spp., Epinotia spp., Formicidae, Geocoris spp., Globitermes sulfureus, Gryllotalpidae, Halotydeus destructor, Hipnodes bicolor, Hydrel- lia philippina, Julus spp., Laodelphax spp., Leptocorsia acuta , Leptocorsia oratorius , Liogenys fuscus, Lucillia spp., Lyogenys fuscus, Mahanarva spp., Maladera matrida, Marasmia spp., Mastotermes spp., Mealybugs, Megascelis ssp, Metamasius hemipter- us, Microtheca spp., Mocis latipes, Murgantia spp., Mythemina separata , Neo- capritermes opacus, Neocapritermes parvus, Neomegalotomus spp., Neotermes spp., Nymphula depunctalis, Oebalus pugnax, Orseolia spp. such as Orseolia oryzae; Ox- ycaraenus hyalinipennis, Plusia spp., Pomacea canaliculata, Procornitermes ssp, Pro- cornitermes triacifer , Psylloides spp., Rachiplusia spp., Rhodopholus spp., Scaptocoris castanea, Scaptocoris spp., Scirpophaga spp. such as Scirpophaga incertulas , Scirpophaga innotata; Scotinophara spp. such as Scotinophara coarctata; Sesamia spp. such as Sesamia inferens, Sogaella frucifera, Solenapsis geminata, Spissistilus spp., Stalk borer, Stenchaetothrips biformis, Steneotarsonemus spinki, Sylepta deroga- ta, Telehin licus, Trichostrongylus spp.

The compounds of the present invention, including their salts, stereoisomers and tau- tomers, 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.

The compounds of the present invention, including their salts, stereoisomers and tau- tomers, are moreover useful for controlling insects of the orders Thysanoptera, Diptera (especially flies, mosquitos), Hymenoptera (especially ants) and Isoptera (especially termites.

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 In- forma, London, 2005.

Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dis- persants, 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, tetra- hydronaphthalene, 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; phospho- nates; 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, sulfosuccin- ates 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, vinyl- alcohols, 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 pol- ybases. 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 alkylisothia- zolinones 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 homoge- neous emulsion. Dilution with water gives an emulsion,

v) Suspensions (SC, OD, FS)

In an agitated ball mill, 10-60 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 micro- emulsion.

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, pel- leting, 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 0.1 to 1000 g per ha, preferably from 1 to 500 g per ha, more preferably from 5 to 500 g per ha, and in particular from 5 to 200 g 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 500 g and most preferably from 5 to 200 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.1 to M.UN.X or F.I to F.XII, can be applied jointly (e.g. after tank mix) or consecutively.

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

M.1 Acetylcholine esterase (AChE) inhibitors from the class of

M.1A carbamates, for example aldicarb, alanycarb, bendiocarb, benfuracarb, butocar- boxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pi- rimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or from the class of

M.1 B organophosphates, for example acephate, azamethiphos, azinphos-ethyl, az- inphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethopro- phos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O- (methoxyaminothio-phosphoryl) salicylate, isoxathion, mala- thion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, prope- tamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vami- dothion;

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, pyra- fluprole and pyriprole;

M.3 Sodium channel modulators from the class of

M.3A pyrethroids, for example acrinathrin, allethrin, d-cis-trans allethrin, d-trans alle- thrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cyper- methrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imipro- thrin, meperfluthrin,metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin and transfluthrin; or

M.3B sodium channel modulators such as DDT or methoxychlor;

M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class of M.4A neonicotinoids, for example acteamiprid, chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds

M.4A.1 : 1 -[(6-chloro-3-pyridinyl)methyl]-2,3,5,6,7,8-hexahydro-9-nitro-(5S,8R)-5,8- Epoxy-1 H-imidazo[1 ,2-a]azepine; or

M.4A.2: 1 -[(6-chloro-3-pyridyl)methyl]-2-nitro-1 -[(E)-pentylideneamino]guanidine; or M4.A.3: 1 -[(6-chloro-3-pyridyl)methyl]-7-methyl-8-nitro-5-propoxy-3,5,6,7-tetrahydro- 2H-imidazo[1 ,2-a]pyridine;

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. tenebri- onis, 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 nereis- toxin 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 methoxyfeno- zide, 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, pyrimidif- en, pyridaben, tebufenpyrad or tolfenpyrad, or M.21 B rotenone;

M.22 Voltage-dependent sodium channel blockers, for example

M.22A indoxacarb, or M.22B metaflumizone, or M.22C 1 -[(E)-[2-(4-cyanophenyl)-1 -[3-

(trifluoromethyl)phenyl]ethylidene]amino]-3-[4-(difluoromethoxy)phenyl]urea;

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, chlorantraniliprole (rynaxypyr®), cyantraniliprole (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 (proposed ISO name: cyclaniliprole), or the compound

M.28.4: methyl-2-[3,5-dibromo-2-({[3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-5- yl]carbonyl}amino)benzoyl]-1 ,2-dimethylhydrazinecarboxylate; or a compound selected from M.28.5a) to M.28.5I):

M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3- chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;

M.28.5b) N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-

2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;

M.28.5c) N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl- phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;

M.28.5d) N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-

(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;

M.28.5e) N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3- chloro-2-pyridyl)-5-(difluoromethyl)pyrazole-3-carboxamide;

M.28.5f) N-[4,6-dibromo-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2- (3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;

M.28.5g) N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-cyano- phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;

M.28.5h) N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3- chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;

M.28.5i) N-[2-(5-amino-1 ,3,4-thiadiazol-2-yl)-4-chloro-6-methyl-phenyl]-5-bromo-2-(3- chloro-2-pyridyl)pyrazole-3-carboxamide;

M.28.5j) 5-chloro-2-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[(1 -cyano-1 -methyl- ethyl)carbamoyl]phenyl]pyrazole-3-carboxamide;

M.28.5k) 5-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-2-(3,5-dichloro-2- pyridyl)pyrazole-3-carboxamide;

M.28.5I) N-[2-(tert-butylcarbamoyl)-4-chloro-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5- (fluoromethoxy)pyrazole-3-carboxamide; or a compound selected from

M.28.6 N2-(1 -cyano-1 -methyl-ethyl)-N1 -(2,4-dimethylphenyl)-3-iodo-phthalamide; or M.28.7 3-chloro-N2-(1 -cyano-1 -methyl-ethyl)-N1 -(2,4-dimethylphenyl)phthalamide; M.28.8a) 1 -(3-Chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-

[(methylamino)carbonyl]phenyl]-3-[[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl]-1 H- pyrazole-5-carboxamide (proposed ISO name: tetraniliprole); or M.28.8b) 1 -(3-Chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-

[(methylamino)carbonyl]phenyl]-3-[[5-(trifluoromethyl)-1 H-tetrazol-1 -yl]methyl]-1 H- pyrazole-5-carboxamide; M.UN.X insecticidal active compounds of unknown or uncertain mode of action, as for example afidopyropen, azadirachtin, amidoflumet, benzoximate, bifenazate, bromo- propylate, chinomethionat, cryolite, dicofol, flufenerim, flometoquin, fluensulfone, flupyradifurone, piperonyl butoxide, pyridalyl, pyrifluquinazon, sulfoxaflor, pyflubumide or the compounds

M.UN.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.UN.X.2: 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-isoxazol-3-yl]- N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]naphthalene-1 -carboxamide, or the compound

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

M.UN.X.6; a compound selected from the group of

M.UN.X.6a) (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro- acetamide;

M.UN.X.6b) (E/Z)-N-[1 -[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2- trifluoro-acetamide;

M.UN.X.6c) (E/Z)-2,2,2-trifluoro-N-[1 -[(6-fluoro-3-pyridyl)methyl]-2- pyridylidene]acetamide;

M.UN.X.6d) (E/Z)-N-[1 -[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro- acetamide;

M.UN.X.6e) (E/Z)-N-[1 -[1 -(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro- acetamide;

M.UN.X.6f) (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro- acetamide;

M.UN.X.6g) (E/Z)-2-chloro-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro- acetamide;

M.UN.X.6h) (E/Z)-N-[1 -[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoro- acetamide and

M.UN.X.6i) (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoro- propanamide.); or of the compounds

M.UN.X.7: 3-[3-chloro-5-(trifluoromethyl)phenyl]-4-oxo-1 -(pyrimidin-5- ylmethyl)pyrido[1 ,2-a]pyrimidin-1 -ium-2-olate; or M.UN.X.8: 8-chloro-N-[2-chloro-5-methoxyphenyl)sulfonyl]-6-trifluoromethyl)- imidazo[1 ,2-a]pyridine-2-carboxamide; or

M.UN.X.9: 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1 - oxothietan-3-yl)benzamide; or

M.UN.X.10: 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole.

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 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 pyrethroid momfluorothrin is known from US 6908945. The pyrazole acaricide pyflubumide is known from

WO 2007/020986. The isoxazoline compounds have been described likewise

M.UN.X.1 in WO 2005/085216, M.UN.X2. in WO 2009/002809 and in

WO 201 1/149749 and the isoxazoline M.UN.X.9 in WO 2013/050317. The pyripyro- pene derivative afidopyropen has been described in WO 2006/129714. The spiroketal- substituted cyclic ketoenol derivative M.UN.X.3 is known from WO 2006/089633 and the biphenyl-substituted spirocyclic ketoenol derivative M.UN.X.4 from

WO 2008/06791 1 . Finally triazoylphenylsulfide like M.UN.X.5 have been described in WO 2006/043635 and biological control agents on basis of bacillus firmus in

WO 2009/124707. The neonicotionids 4A.1 is known from WO 20120/069266 and WO 201 1/06946, the M.4.A.2 from WO 2013/003977, the M4.A.3.from

WO 2010/069266. The anthranilamide compounds M.28.8a) and M.28.8b) are known from WO2010/069502.

The Metaflumizone analogue M.22C is described in CN 10171577. 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 2005/077934. The hydrazide compound M.28.4 has been described in WO 2007/043677. The anthranilamides M.28.5a) to M.28.5h) can be prepared as described in WO 2007/006670, WO 2013/024009 and WO 2013/024010, the anthranilamide Μ.28.5Ϊ) is described in WO 201 1/085575, the M.28.5j) in

WO 2008/134969, the M.28.5k) in US 201 1/046186 and the M.28.5I) in

WO 2012/034403. The diamide compounds M.28.6 and M.28.7 can be found in CN 102613183.

The compounds M.UN.X.6a) to M.UN.X.6i) listed in M.UN.X.6 have been described in WO 2012/029672. The mesoionic antagonist compound M.UN.X.7 was described in WO 2012/0921 15, the nematicide M.UN.X.8 in WO 2013/055584 and the Pyridalyl-type analogue M.UN.X.10 in WO 2010/060379. Preferred additional pesticidally active ingredients are those selected from the IRAC group 1 , the Acetylcholinesterase (AChE) inhibitors, herein from the group 1 A (Car- bamtes) Thiodicarb, Methomyl and Carbaryl, and from the group

1 B(Organophosphates), especially Acephate, Chlorpyriphos and Dimethoate, from the group 2B, the fiproles, here especially ethiprole and fipronil, from the group 3, the pyrethroids, here especially lambda-cyhalothrin, alpha-cypermethrin or deltametrin, and from the group 4A, the neonicotinoids, here especially acetamiprid, clothianidin, dinote- furan, imidacloprid, nitenpyram, thiacloprid or thiomethoxam. Especially combinations of compounds of the invention with fiproles, neonictinoids or pyrethroids may possibly exhibit synergistic control of stinkbugs (according to the Colby formula), in particular Euschistus, e.g. Euschistus heros.

The following list F of active substances, in conjunction with which the compounds ac- cording 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:

strobilurins: azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, ene- stroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, triclopy- ricarb/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, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fenhexamid, fluopyram, flutolanil, furametpyr, isopyrazam, isotianil, mepronil, oxycar- boxin, 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 (fluxapyroxad), N-(4'-trifluoromethylthiobiphenyl-2- yl)-3 difluoromethyl-1 -methyl-1 H pyrazole-4-carboxamide, N-(2-(1 ,3,3-trimethyl-butyl)- phenyl)-1 ,3-dimethyl-5 fluoro-1 H-pyrazole-4 carboxamide, 3-(difluoromethyl)-1 -methyl- N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1 -methyl-N- (1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1 ,3-dimethyl-N-(1 ,1 ,3- trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1 ,5-dimethyl-N-(1 ,1 ,3- trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(difluoromethyl)-1 ,5-dimethyl-N-(1 ,1 ,3- trimethylindan-4-yl)pyrazole-4-carboxamide, 1 ,3,5-trimethyl-N-(1 ,1 ,3-trimethylindan-4- yl)pyrazole-4-carboxamide, 3-(difluoromethyl)-1 -methyl-N-(1 ,1 ,3-trimethylindan-4- yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1 -methyl-N-(1 ,1 ,3-trimethylindan-4- yl)pyrazole-4-carboxamide, 1 ,3-dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4- carboxamide, 3-(trifluoromethyl)-1 ,5-dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4- carboxamide, 3-(difluoromethyl)-1 ,5-dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4- carboxamide, 1 ,3,5-trimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide; F.I-3) Inhibitors of complex III at Qi site: cyazofamid, amisulbrom, [(3S,6S,7R,8R)-8- benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1 ,5-di- oxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4- methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl]

2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy- pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[[3-(1 ,3-benzodioxol-5-ylmethoxy)-4-methoxy-pyridine-2- carbonyl]amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate,

3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-methyl-4,9- dioxo-8-(phenylmethyl)-1 ,5-dioxonan-7-yl 2-methylpropanoate;

F.I-4) Other respiration inhibitors (complex I, uncouplers) diflumetorim; (5,8-difluoro- quinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl}-amine; tecnazen; ametoctradin; silthiofam; nitrophenyl derivates: binapacryl, dinobuton, di- nocap, fluazinam, ferimzone, nitrthal-isopropyl,

and including 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, flusi- lazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobuta- nil, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebu- conazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1 -[re/- (2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1 H- [1 ,2,4]triazole, 2-[re/-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]- 2H-[1 ,2,4]triazole-3-thiol;

imidazoles: imazalil, pefurazoate, oxpoconazole, prochloraz, triflumizole;

pyrimidines, pyridines and piperazines: fenarimol, nuarimol, pyrifenox, triforine, 1 -[rel- (2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1 H- [1 ,2,4]triazole, 2-[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]- 2H-[1 ,2,4]triazole-3-thiol;

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, met- alaxyl, 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, fluopico- lide, zoxamide;

F.IV-3) Actin inhibitors: benzophenones: metrafenone, pyriofenone;

F.V) Inhibitors of amino acid and protein synthesis

F.V-1 ) Methionine 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, mildiomy- cin, 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 acids:

1 -[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1 -piperidinyl]-2-[5- methyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl]ethanone, carbamates: propamocarb, pro- pamocarb-hydrochlorid,

F.VII-5) fatty acid amide hydrolase inhibitors: 1 -[4-[4-[5-(2,6-difluorophenyl)-4,5- dihydro-3-isoxazolyl]-2-thiazolyl]-1 -piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1 H- pyrazol-1 -yl]ethanone;

F.VIII) Inhibitors with Multi Site Action F.VIII-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, flusulfa- mide, hexachlorobenzene, pentachlorphenole and its salts, phthalide, tolylfluanid, N-(4- chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;

F.VIII-4) Guanidines and other: guanidine, dodine, dodine free base, guazatine, guaza- tine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate), 2,6- dimethyl-1 H,5H-[1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone;

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, diphenyla- min, fenpyrazamine, flumetover, flusulfamide, flutianil, methasulfocarb, nitrapyrin, ni- trothal-isopropyl, oxathiapiprolin, oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide, 2-butoxy-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-trifluoromethyl-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-trifluoromethyl-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]-pyridine, 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) cyclopro- panecarboxylic 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.XII) Growth regulators: abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flur- primidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N 6-benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium), prohydro- jasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5 tri iodobenzoic acid, trinexapac-ethyl and uniconazole;

F.XII I) Biological control agents

Ampelomyces quisqualis (e.g. AQ 10^® from Intrachem Bio GmbH & Co. KG, Germany), Aspergillus flavus (e.g. AFLAGUARD^® from Syngenta, CH), Aureobasidium pullulans (e.g. BOTECTOR^® from bio-ferm GmbH, Germany), Bacillus pumilus (e.g. NRRL Accession No. B-30087 in SONATA^® and BALLAD^® Plus from AgraQuest Inc., USA), Bacillus subtilis (e.g. isolate NRRL-Nr. B-21661 in RHAPSODY^®, SERENADE^® MAX and SERENADE^® ASO from AgraQuest Inc., USA), Bacillus subtilis var. amyloliquefaciens FZB24 (e.g. TAEGRO^® from Novozyme Biologicals, Inc., USA), Candida oleophila I-82 (e.g. ASPIRE^® from Ecogen Inc., USA), Candida saitoana (e.g. BIOCURE^® (in mixture with lysozyme) and BIOCOAT^® from Micro Flo Company, USA (BASF SE) and Arysta), Chitosan (e.g. ARMOUR-ZEN from BotriZen Ltd., NZ), Clonostachys rosea f. catenula- fa, also named Gliocladium catenulatum (e.g. isolate J 1446: PRESTOP^® from Verdera, Finland), Coniothyrium minitans (e.g. CONTANS^® from Prophyta, Germany),

Cryphonectria parasitica (e.g. Endothia parasitica from CNICM, France), Cryptococcus albidus (e.g. YIELD PLUS^® from Anchor Bio-Technologies, South Africa), Fusarium oxysporum (e.g. BIOFOX^® from S.I.A.P.A., Italy, FUSACLEAN^® from Natural Plant Pro- tection, France), Metschnikowia fructicola (e.g. SHEMER^® from Agrogreen, Israel),

Microdochium dimerum (e.g. ANTIBOT^® from Agrauxine, France), Phlebiopsis gigantea (e.g. ROTSOP^® from Verdera, Finland), Pseudozyma flocculosa (e.g. SPORODEX^® from Plant Products Co. Ltd., Canada), Pythium oligandrum DV74 (e.g. POLYVER- SUM^® from Remeslo SSRO, Biopreparaty, Czech Rep.), Reynoutria sachlinensis (e.g. REGALIA^® from Marrone Biolnnovations, USA), Talaromyces flavus V1 17b (e.g. PRO- TUS^® from Prophyta, Germany), Trichoderma asperellum SKT-1 (e.g. ECO-HOPE^® from Kumiai Chemical Industry Co., Ltd., Japan), T. atroviride LC52 (e.g. SENTINEL^® from Agrimm Technologies Ltd, NZ), T. harzianum T-22 (e.g. PLANTSHIELD^® der Fir- ma BioWorks Inc., USA), T. harzianum JH 35 (e.g. ROOT PRO^® from Mycontrol Ltd., Israel), T. harzianum T-39 (e.g. TRICHODEX^® and TRICHODERMA 2000^® from Mycontrol Ltd., Israel and Makhteshim Ltd., Israel), T. harzianum and T. viride (e.g. TRI- CHOPEL from Agrimm Technologies Ltd, NZ), T. harzianum ICC012 and T. viride ICC080 (e.g. REMEDIER^® WP from Isagro Ricerca, Italy), T. polysporum and T. harzianum (e.g. BINAB^® from BINAB Bio-Innovation AB, Sweden), T. stromaticum (e.g. TRICOVAB^® from C.E.P.L.A.C., Brazil), T. virens GL-21 (e.g. SOILGARD^® from Certis LLC, USA), T. viride {e.g. TRIECO^® from Ecosense Labs. (India) Pvt. Ltd., Indien, BIOCURE^® F from T. Stanes & Co. Ltd., Indien), T. viride TV1 (e.g. T. viride TV1 from Ag- ribiotec srl, Italy), Ulocladium oudemansii HRU3 (e.g. BOTRY-ZEN^® from Botry-Zen Ltd, NZ).

The commercially available compounds II of the group F listed above may be found in The Pesticide Manual, 15th Edition, C. D. S. Tomlin, British Crop Protection Council (201 1 ) among other publications. Their preparation and their activity against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by lUPAC nomenclature, their preparation and their fungicidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP A 141 317; EP-A 152 031 ; EP-A 226 917; EP A 243 970; EP A 256 503; EP-A 428 941 ; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP A 1 201 648; EP A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413;

WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ;

WO 01/56358; WO 02/22583; WO 02/40431 ; WO 03/10149; WO 03/1 1853;

WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609;

WO 03/74491 ; WO 04/49804; WO 04/83193; WO 05/120234; WO 05/123689;

WO 05/123690; WO 05/63721 ; WO 05/87772; WO 05/87773; WO 06/15866;

WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 1 1/028657).

The compounds of the invention may be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.

Examples of suitable synergists for use in the compositions include piperonyl butoxide, sesamex, safroxan and dodecyl imidazole.

Suitable herbicides and plant-growth regulators for inclusion in the compositions will depend upon the intended target and the effect required. An example of a rice selective herbicide which may be included is propanil. An example of a plant growth regulator for use in cotton is PIX™.

Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same.

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 insec- ticidally 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 ethox- ylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzo- ate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, pro- pellants 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, knit- goods, 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, Me- thylneodecanamide (MNDA), a pyrethroid not used for insect control such as {(+/-)-3- allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate (Esbiothrin), a repel- lent 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), Cy- mopogan 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 in- vention, 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 lim- ited 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, imid- azolinones, 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, poly- saccharides 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 pre- sent 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 "un- sown 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 pesti- cides 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 oral- ly, 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, chig- gers, 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, Peri- planeta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis,

flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anas- trepha 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 inor- nata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intes- tinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Lep- toconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus ar- gentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcoph- aga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Taba- nus 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, Bo- vicola 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, Ornithodo- rus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonys- sus 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., Tricho- dectes spp., and Felicola spp,

Roundworms Nematoda: Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Tri- churidae) Trichuris spp., Capillaria spp,

Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp,

Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunosto- mum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oe- sophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stepha- nurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus, and Dioc- tophyma 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 Habro- nema 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., Dicro- coelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilhar- zia 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 applica- tion, 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.

The compounds I of formula I can be prepared according to standard methods of organic chemistry, e.g. by the methods or working examples described in

WO 2013/063282. The characterization can be done by coupled High Performance Liquid Chromatography/mass spectrometry (HPLC/MS), by NMR or by their melting points.

Method A: Analytical HPLC column: RP-18 column Chromolith Speed ROD 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.

Method B: Analytical UPLC column: Phenomenex Kinetex 1 ,7 μηι XB-C18 100A; 50 x 2.1 mm; mobile phase: A: water + 0.1 % trifluoroacetic acid (TFA); B: acetonitrile + 0.1 % TFA; gradient: 5-100% B in 1.50 minutes; 100% B 0.20 min; flow: 0,8-1 ,0mL/min in 1 ,50 minutes at 60°C.

MS-method: ESI positive. ¹H-NMR. The signals are characterized by chemical shift (ppm) vs. tetramethylsilane, 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.

Preparation Examples:

logP determinations were performed via capillary electrophorese on a cePro9600™ from CombiSep.

Preparation Examples

Example 1

1 -[[1 -(3,4-Dichlorophenyl)-3-(2-fluorophenyl)pyrazol-4-yl]methyl]-4-methoxy-piperidine

4-(Bromomethyl)-1 -(3,4-dichlorophenyl)-3-(2-fluorophenyl)pyrazole was prepared ac- cording to WO 2013/063282. To a solution of 4-(bromomethyl)-1 -(3,4-dichlorophenyl)- 3-(2-fluorophenyl)pyrazole (350 mg, 0.87 mmol) in acetonitrile (20 ml.) was added 4- methoxypiperidine (546 mg, 4.74 mmol, 5.4 equiv.) at room temperature, followed by potassium carbonate (655 mg, 4.74 mmol, 5.4 equiv.). After 18 h at this temperature, water was added and the mixture was extracted with ethyl acetate. After drying of the organic layer over sodium sulfate, the solvent was evaporated in vacuum and the residue was purified by chromatography on silica gel to give the title compound (300 mg, 79%).

HPLC-MS: 1 .051 min, m/z 434.7 (M)⁺ (Method B)

H-NMR (400 MHz, DMSO) δ: 1 .29 (m, 2H), 1 .74 (m, 2H), 2.00 (m, 2H), 2.58 (m, 2H), 3.10 (m, 1 H), 3.38 (s, 2H), 7.28-7.35 (m, 2H), 7.51 (m, 1 H), 7.66 (m, 1 H), 7.75 (d, 1 H), 7.92 (dd, 1 H), 8.22 (d, 1 H), 8.63 (s, 1 H).

In analogy to the above method, the compounds of formula (I.A) and (I.B) summarized in tables A.1 and B.1

Table A.1 o. Z Z² J¹ J² X-L-A MS RT[min] m/z method

IA-1 3-chloro-4- 2-fluo- C=0 c=o NCHs B 1 .264 430.8 fluorophenyl rophenyl

IA-2 4-chloro- 2-fluo- c=o c=o NCHs B 1 .242 412.8 phenyl rophenyl

Table B.1

o. Z Z² L-A MS RT[min] m/z method

IB-1 3,4-dichloro- 2-fluoro- OCHs B 1 .051 434.7 phenyl phenyl

IB-2 3,4- 2-fluoro- methoxyiminomethyl B 1 .080 463.6 dichlorophenyl phenyl

IB-3 4-(trifluoro- 2-fluoro- methoxyiminomethyl B 1 .059 461 .8 methyl)phenyl phenyl

IB-4 3,4-dichloro- 2-fluoro- OCH2CH3 B 1 .070 447.9 phenyl phenyl

IB-5 3,4-dichloro- 2-fluoro- propanoyloxy B 1 .096 476.7 phenyl phenyl

IB-6 3,4-dichloro- 2-fluoro- ethoxyiminomethyl B 1 .131 475.7 phenyl phenyl

IB-7 4-(trifluoro- 2-fluoro- 3-chloroallyloxy- B 1 .142 521 .8 methyl)phenyl phenyl iminomethyl

IB-8 4-(trifluoro- 2-fluoro- ethoxyiminomethyl B 1 .072 475.8 methyl)phenyl phenyl

IB-9 4-(trifluoro- 2-fluoro- 2-(4-chlorophenyl)- B 1 .187 585.0 methyl)phenyl phenyl ethoxyiminomethyl

IB-10 4-(trifluoro- 2-fluoro- cyclopropylmethoxy- B 1 .099 500.9 methyl)phenyl phenyl iminomethyl o. Z Z² L-A MS RT[min] m/z method

IB-1 1 4-(trifluoro- 2-fluoro- allyloxyiminomethyl B 1 .073 487.0 methyl)phenyl phenyl

IB-12 4-(trifluoro- 2-fluoro- 2,2,2-trifluoroethoxy- B 1 .099 528.9 methyl)phenyl phenyl iminomethyl

IB-13 4-(trifluoro- 2-fluoro- prop-2-ynoxy- B 1 .051 484.9 methyl)phenyl phenyl iminomethyl

IB-14 3,4-dichloro- 2-fluoro- (methylcarbamoyl- B 1 .1 1 1 502.5 phenyl phenyl hydrazono)methyl

IB-15 3,4-dichloro- 4-fluoro- ethoxyiminomethyl B 1 .1 12 474.8 phenyl phenyl

IB-16 5-(trifluoro- 2,4- ethoxyiminomethyl B 1 .058 493.9 methyl)-2-pyridyl difluoro- phenyl

IB-17 3,4-dichloro- 2-fluoro- (2,2,2-trifluoro- B 1 .061 571 .2 phenyl phenyl ethylcarbamoylhyd- razono)methyl

IB-18 3,4-dichloro- 2-fluoro- (acetylhydrazo- B 0.981 488.3 phenyl phenyl no)methyl

IB-19 3,4-dichloro- 2-fluoro- hydroxyiminomethyl B 1 .005 448.6 phenyl phenyl

IB-20 3,4-dichloro- 2-fluoro- benzyloxyiminome- B 1 .186 537.3 phenyl phenyl thyl

IB-21 4-(trifluoro- 2,4- ethoxyiminomethyl B 1 .120 509.5 methoxy)phenyl difluoro- phenyl

IB-22 4-(trifluoro- 2-fluoro- 2-chloroallyloxy- B 1 .170 520.5 methyl)phenyl phenyl iminomethyl

IB-23 4-(trifluoro- 2-fluoro- (2,4-difluorophenyl)- B 1 .223 572.5 methyl)phenyl phenyl methoxyiminomethyl

IB-24 3,4-dichloro- 2-fluoro- 2,2,2-trifluoroethoxy- B 1 .158 529.3 phenyl phenyl iminomethyl

IB-25 3,4-dichloro- 2-fluoro- (ethylcarbamothioyl- B 1 .089 533.4 phenyl phenyl hydrazono)methyl

B. 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 Boll weevil (Anthonomus grandis)

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

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

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

In this test, compounds IB-6, IB-7, IB-9, IB-10, IB-1 1 , IB-12, IB-15, IB-16, IB-21 , IB-22, IB-23, IB-24, IB-25 at 2500 ppm showed over 75 % mortality in comparison with untreated controls.

B.2 Orchid thrips (dichromothrips corbetti) Dichromothrips corbetti adults used for bioassay were obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the test compound is diluted in a 1 :1 mixture of acetone:water (vohvol), plus Kinetic HV at a rate of 0.01 % v/v. Thrips potency of each compound was evaluated by using a floral-immersion technique. All petals of individual, intact orchid flowers were dipped into treatment solution and allowed to dry in Petri dishes. Treated petals were placed into individual re- sealable plastic along with about 20 adult thrips. All test arenas were held under continuous light and a temperature of about 28°C for duration of the assay. After 3 days, the numbers of live thrips were counted on each petal. The percent mortality was recorded 72 hours after treatment.

In this test, compounds IA-1 , IA-2, IB-1 , IB-5, IB-6, IB-12, IB-15, IB-16, IB-2, IB-21 at 500 ppm showed over 75 % mortality in comparison with untreated controls

B.3 Cowpea aphid (aphis craccivora)

The active compound was dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water : acetone. Surfactant (Kinetic HV) was added at a rate of 0.01 % (vol/vol). The test solution was prepared at the day of use. Potted cowpea plants were colonized with approximately 50 - 100 aphids of various stages by manually transferring a leaf tissue cut from infested plant 24 hours before application. Plants were sprayed after the pest population has been recorded. Treated plants were maintained on light carts at about 28°C. Percent mortality was assessed after 72 hours.

In this test, compound IA-1 at 500 ppm showed over 75 % mortality 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.

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, compounds IB-1 , IB-2, IB-3, IB-6, IB-7, IB-8, IB-9, IB-10, IB-1 1 , IB-12, IB- 15, IB-16, IB-17, IB-18, IB-19, IB-20, IB-21 , IB-22, IB-23, IB-24, IB-25 at 2500 ppm showed over 75 % mortality in comparison with untreated controls. B.5 Tobacco budworm (Heliothis virescens)

For evaluating control of tobacco budworm (Heliothis virescens) the test unit consisted of 96-well-microtiter plates containing an insect diet and 15-25 H. virescens eggs. The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 10 μΙ, using a custom built micro atomizer, at two replications.

After application, microtiter plates were incubated at about 28 + 1 °C and about 80 + 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed. In this test, compounds IB-2, IB-3, IB-6, IB-7, IB-8, IB-9, IB-10, IB-1 1 , IB-12, IB-14, IB- 15, IB-16, IB-19, IB-20, IB-21 , IB-22, IB-23, IB-24 at 2500 ppm showed over 75% mortality in comparison with untreated controls.

B.6 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, compounds IA-2, IB-2, IB-3, IB-5, IB-22 at 2500 ppm showed over 75 % mortality in comparison with untreated controls. B.7 Rice green leafhopper (Nephotettix virescens)

Rice seedlings were cleaned and washed 24 hours before spraying. The active compounds were formulated in 1 :1 acetone:water (vohvol), and 0.01 % vol/vol surfactant (Kinetic HV) was added. Potted rice seedlings were sprayed with 5-6 ml test solution, air dried, covered with Mylar cages 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, compounds IB-2, IB-3, IB-6, IB-1 1 , IB-13, IB-16 at 500 ppm showed over 75 % mortality in comparison with untreated controls.

B.8 Diamond back moth (Plutella xylostella)

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

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

In this test, compounds IB-1 , IB-2, IB-3, IB-4, IB-6, IB-7, IB-8, IB-9, IB-10, IB-1 1 , IB-12, IB-13, IB-14, IB-15, IB-16, IB-17, IB-18, IB-19, IB-20, IB- 21 at 500 ppm showed over 75 % mortality in comparison with untreated controls. B.9 Southern armyworm (Spodoptera eridania), 2nd instar larvae

The active compounds were formulated by a Tecan liquid handler in 100%

cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppm solution was serially diluted in 100% cyclohexanone to make interim solutions. These served as stock solutions for which final dilutions were made by the Tecan in 50% acetone:50% water (v/v) into 5 or 10ml glass vials. A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01 % (v/v). The vials were then inserted into an automated electrostatic sprayer equipped with an atomizing nozzle for application to

plants/insects.

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 au- tomated 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, compounds IB-4, IB-6, IB-14, IB-15, IB-19, IB-21 at 500 ppm showed over 75 % mortality in comparison with untreated controls.

Claims

1 . Pyrazole compounds of formula I

wherein

Q is a radical of formula Q-1 , Q-2, Q-3 or Q-4

(Q-1) (Q-2)

(Q-3) (CM)

J¹ is a direct bond, -C(R^3aR^3b)-, -C(R^3aR^3b)-C(R^3aR^3b)- or -C(=B)-;

J² is a direct bond, -C(R^3cR^3d)- or -C(=B)- X is selected from CR^3e and N; is a single bond or is selected from the group consisting of Ci-Ci2-alkylene, Ci-Ci2-haloalkylene, C2-Cio-alkenylene, C2-Cio-haloalkenylene, C2-C10- alkynylene, C2-Cio-haloalkynylene, Cs-Cs-cycloalkylene and C3-C8- halocycloalkylene, where the 8 aforementioned radicals can be substituted with one or more radicals R¹⁵; is a group A1 , A2, A3, A4, A5 or A6, wherein

A1 is selected from -CR^d=N-R^c , -C(=N-N(R^c )R^c2)R^d and

-C(=NR^c )N(R^c2)R^c3;

A2 is selected from -SF₅ and -SCN; and in case that L is a single bond, A2 is additionally selected from -OR^a; and in case that L is a single bond and X is N, A2 is additionally selected from hydrogen; and in case that L is a single bond, X is N and at least one of J¹ and J² is -C(=B)-, A2 is additionally selected from Ci-C6-alkyl and C1-C6- haloalkyl;

A3 is selected from -S(=N-R^c1)R^a, -S(=0)(=N-R^c1)-R^a and

-C(=0)-N=S(R^a)₂;

A4 is selected from -NR^c -S-R^a, -NR^c -S(=0)-R^a, -NR^c -S(=0)₂-R^a;

-NR^c -S-N(R^c2)R^c3; -NR^c -S(=0)-N(R^c2)R^c3 and

-NR^c -S(=0)₂-N(R^c2)R^c3;

A5 is selected from -N(=C(R^d)R^b) and -N=(C(R^d)N(R^c )R^c2); and

A6 is a 3-, 4-, 5-, 6-, 7- or 8-membered non-aromatic heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, S, O, NO, SO and SO2 and optionally also 1 or 2 groups

C(=0) or C(=S) as ring members, where the heterocyclic ring may be substituted by one or more radicals R¹⁶; each B is independently selected from O, S, CR^d1R^d2 and NR^c1; is selected from phenyl which may carry 1 , 2, 3, 4 or 5 radicals R^4a; a 5- or 6-membered heteroaromatic monocyclic ring and a 8-, 9- or 10-membered heteroaromatic bicyclic ring, the heteroaromatic mono- and bicyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from O, N and S as ring members, where the heteroaromatic mono- or bicyclic ring may carry 1 , 2 or 3 radicals R^4a; is selected from phenyl which may carry 1 , 2, 3, 4 or 5 radicals R^4b; a 5- or 6-membered heteroaromatic monocyclic ring and a 8-, 9- or 10-membered heteroaromatic bicyclic ring, the heteroaromatic mono- and bicyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from O, N and S as ring mem- bers, where the heteroaromatic mono- or bicyclic ring may carry 1 , 2 or 3 radicals R^4b; h R^a is independently selected from the group consisting of hydrogen, C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, wherein the aliphatic and cycloaliphatic moieties in the 6 aforementioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents selected from Ci-C4-alkoxy and oxo;

phenyl, benzyl and pyridyl, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Ci-C6-alkoxycarbonyl;

R^b1 and R^b2, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, Ci-C6-alkyl, C2- C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, wherein the aliphatic and cycloaliphatic moieties in the 8 aforementioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents selected from C1-C4- alkoxy and oxo;

phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkoxycarbonyl, Ci-C6-alkylamino and di-(Ci-C6-alkyl)amino;

R^c1, R^c2 and R^c3, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, cyano, hy- droxyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C1-C6- alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-Cs-cycloalkyloxy, C1-C6- alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, wherein the aliphatic and cycloaliphatic moieties in the 10 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁸;

-C(=0)R , -C(=0)NR R², -C(=S)R , -C(=S)NR R²,

phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkoxycarbonyl, Ci-C6-alkylamino and di-(Ci-C6-alkyl)amino; or R^c1 and R^c2, or R^c2 and R^c3, 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 which may additionally 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 be substituted with one or more substituents selected from halogen, C1-C4- haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;

R^d, R^d1 and R^d2, independently of each other and independently of each occur- rence, are selected from the group consisting of hydrogen, halogen, cyano, nitro, -OH, -SH, -SCN, Ci-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈- cycloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, C1-C6- alkylsulfonyl, wherein the aliphatic and cycloaliphatic moieties in the 8 last- mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents selected from Ci-C4-alkoxy and oxo;

-OR^a, -NR^c R^c2, -S(0)_nR^a, -S(0)_nNR^c R^c2, -C(=0)R^b, -C(=0)NR^c R^c2, -C(=0)OR^a, -C(=S)R^b, -C(=S)NR^c R^c2, -C(=S)OR^a, -C(=S)SR^a,

-C(=NR^c1)R^b, -C(=NR^c1)NR^c2R^c3, phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may carry one or more substitu- ents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and

Ci-C6-haloalkoxy;

R^1a is selected from hydrogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6- cycloalkyl, C₃-C₆-halocycloalkyl, carboxyl, -C(=0)R^5a, -C(=0)OR^6a and -C(=0)NR^7aR^8a;

R^1b is selected from hydrogen and Ci-C6-alkyl;

-C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, S(0)_nR¹¹, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyI, Cs-Cs-cycloalkyl- Ci-C4-alkyl, Cs-Cs-cycloalkenyl, wherein the aliphatic and cycloaliphatic moieties in the 6 last-mentioned radicals may be partially or fully halogen- ated and/or may carry 1 or 2 substituents R¹⁷;

R^2b and R^2d, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, halogen, cyano, nitro, -C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, NR⁹R¹⁰, S(0)_nR¹¹, S(0)₂NR⁹R¹⁰, Ci-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈- cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, Cs-Cs-cycloalkenyl, wherein the aliphatic and cycloaliphatic moieties in the 6 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R⁴; and a 5- or 6-membered het- eroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R⁴;

-C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, OR¹², S(0)_nR¹¹, d-Ce-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, C₃-C₈- cycloalkyl-Ci-C4-alkyl, Cs-Cs-cycloalkenyl, wherein the aliphatic and cycloaliphatic moieties in the 6 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷;

R^3b, R^3d and R^3e, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, halogen, cyano, nitro, -C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, NR⁹R¹⁰, OR¹², S(0)_nR¹¹, S(0)₂NR⁹R °, Ci-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆- alkynyl, C3-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, Cs-Cs-cycloalkenyl, wherein the aliphatic and cycloaliphatic moieties in the 6 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R⁴; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R⁴; or R^2a and R^2b, or R^2a and R^2c, or R^2c and R^2d, or R^3a and R^3b, or R^3a and R^3c, or R^3c and R^3d, or R^2a and R^3a, or R^2a and R^3c, or R^2c and R^3c, or R^2a and R^3e, or R^2c and R^3e, or R^3a and R^3e, or R^3c and R^3e, together with the carbon atoms they are bound to, may form a 3- 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated carbocyclic or heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, S0₂, C(O) and C(S) as ring members, where the carbocyclic or heterocyclic ring may carry 1 , 2 or 3 substituents selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; R⁴, R^4a and R^4b, independently of each other and independently of each occurrence, are selected from the group consisting of halogen, cyano, nitro, -C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, NR⁹R¹⁰, OR¹², S(0)_nR¹¹, S(0)₂NR⁹R¹⁰, Ci-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cy- cloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents

R¹³; or two radicals R⁴ or two radical R^4a or two radicals R^4b, when bound to adjacent carbon atoms, together with these carbon atoms may form a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated carbocyclic or heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroa- tom groups selected from N, O, S, NO, SO, S0₂, C(O) and C(S) as ring members, where the carbocyclic or heterocyclic ring may carry 1 , 2 or 3 substituents selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; each R⁵ is independently selected from the group consisting of hydrogen, C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last- mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R¹³; each R^5a is independently selected from the group consisting of hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl and C3-Cs-halocycloalkyl; each R⁶ is independently selected from the group consisting of hydrogen, C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last- mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroa- toms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R¹³;

R^6a is independently selected from the group consisting of hydrogen, Ci-C6- alkyl and Ci-C6-haloalkyl;

R⁷ and R⁸, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R¹³; or R⁷ and R⁸, together with the nitrogen atom they are bound to, form a 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, where the heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from O, N, S, NO, SO, SO2, C(O) and C(S) as ring members; where the heterocyclic ring may carry 1 , 2 or 3 substituents R¹³; and R^8a, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, Ci-C6-alkyl and C1-C6- haloalkyl;

R⁹ and R¹⁰, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, -C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, Ci-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆- alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaro- matic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R¹³; or R⁹ and R¹⁰, together with the nitrogen atom they are bound to, form a 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, where the heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from O, N , S, NO, SO, SO2, C(O) and C(S) as ring members; where the heterocyclic ring may carry 1 , 2 or 3 substituents R¹³;

R^9a and R^10a, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, -C(=0)R^5a, -C(=S)R^5a, -C(=0)OR^6a, -C(=0)N R^7aR^8a; -C(=S)N R^7aR^8a, Ci-C₆-alkyl and Ci-C₆- haloalkyl; each R^{1 1} is independently selected from Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cy- cloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R¹³; each R^{1 1 a} is independently selected from Ci-C6-alkyl and Ci-C6-haloalkyl; each R¹² is independently selected from hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁷; phenyl which may carry 1 , 2 or 3 substituents R¹³; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteroaromatic ring may carry 1 , 2 or 3 substituents R¹³; each R^12a is independently selected from hydrogen, Ci-C6-alkyl and C1-C6- haloalkyl; each R¹³ is independently selected from the group consisting of halogen, cyano, nitro, -C(=0)R^5a, -C(=S)R^5a, -C(=0)OR^6a, -C(=0)N R^7aR^8a; -C(=S)N R^7aR^8a, N R^9aR^10a, OR^12a, S(0)_nR^{1 1 a}, S(O)₂N R ^aR ^0a, Ci-C₆-alkyl, C₂-C₆-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl and C3-Cs-cycloalkyl-Ci-C4-alkyl, wherein the aliphatic and cycloaliphatic moieties in the 5 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents

R¹⁷; or two radicals R¹³, when bound to adjacent carbon atoms, together with these carbon atoms may form a 3- 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated carbocyclic or heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, C(O) and C(S) as ring members, where the carbocyclic or heterocyclic ring may carry 1 , 2 or 3 substituents selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;

R¹⁴ is selected from the group consisting of hydrogen, halogen, cyano, nitro, -C(=0)R⁵, -C(=S)R⁵, -C(=0)OR⁶, -C(=0)NR⁷R⁸; -C(=S)NR⁷R⁸, NR⁹R¹⁰, OR¹², S(0)_nR¹¹, S(0)₂NR⁹R¹⁰, Ci-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-

Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl and Cs-Cs-cycloalkenyl, wherein the aliphatic and cycloaliphatic moieties in the 6 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R ⁷; each R¹⁵ is independently selected from cyano, nitro, -OH, -SH, -SCN, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, Ci-C6-alkylcarbonyl, C1-C6- haloalkylcarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxycarbonyl, C1-C6- alkylamino, Ci-C6-dialkylamino, Ci-C6-alkylaminocarbonyl, C1-C6- dialkylaminocarbonyl, phenyl which may carry 1 , 2, 3, 4 or 5 radicals R¹⁶; and a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, S, O, NO, SO and SO2 and optionally also 1 or 2 groups C(=0) or C(=S) as ring members, where the heterocyclic ring may be substituted by one or more radicals R¹⁶; and

as a substituent on a cycloalkylene or halocycloalkylene moiety, R¹⁵ is additionally selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl; each R¹⁶ is independently selected from halogen, nitro, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxycarbonyl, Ci-C6-alkylamino, C1-C6- dialkylamino, Ci-C6-alkylaminocarbonyl and Ci-C6-dialkylaminocarbonyl; each R¹⁷ is independently selected from halogen, cyano, nitro, OR^12a and

S(0)_nR^11a; and as a substituent on a cycloalkyl, cycloalkyl-alkyl or cycloal- kenyl moiety, R¹⁷ is additionally selected from Ci-C4-alkyl and C1-C4- haloalkyl; each R¹⁸ is independently selected from cyano, nitro, OR^12a, oxo, S(0)_nR^11a,

C3-C8-cycloalkyl, Cs-Cs-halocycloalkyl, where the cycloaliphatic moieties in the two last-mentioned radicals may be substituted by one or more radicals selected oxo and cyano; Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-haloalkoxycarbonyl, Ci-C6-alkylamino, C1-C6- dialkylamino, Ci-C6-alkylaminocarbonyl, Ci-C6-dialkylaminocarbonyl, phenyl which may carry 1 , 2, 3, 4 or 5 radicals R¹⁶; and a 3-, 4-, 5-, 6-, 7- or 8- membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, S, O, NO, SO and SO2 and optionally also 1 or 2 groups C(=0) or C(=S) as ring members, where the heterocyclic ring may be substituted by one or more radicals R¹⁶;

and as a substituent on a cycloalkyl moiety, R¹⁸ is additionally selected from Ci-C4-alkyl and Ci-C4-haloalkyl; m is 0 or 1 ; and n is 0, 1 or 2; or the N-oxides or the tautomers or the agriculturally acceptable salts thereof; except for the compound I wherein Z¹ is 4-(trifluoromethoxy)phenyl, Z² is 2- fluorophenyl, Q is Q-1 , X is CR^3e, R^1a, R^1b, R^2a, R^2b, R^2c, R^2d, R^3e and R¹⁴ are hydrogen, J¹ and J² are CH2, L is a bond and A is NHSO2CH3;

except for the compounds I wherein Z¹ is 4-chlorophenyl, Z² is 2-fluorophenyl, Q is Q-1 , X is CR^3e, R^1a, R^1b, R^2a, R^2b, R^2c, R^2d, R^3e and R¹⁴ are hydrogen, J¹ and J² are CH2, L is a bond and A is 2-oxo-1 ,3-oxazolidin-3-yl or 4,5-dihydro-1 ,3-oxazol- 2-yl; except for the compound I wherein Z¹ is 3-chloro-fluorophenyl, Z² is 2- fluorophenyl, Q is Q-1 , X is CR^3e, R^1a, R^1b, R^2a, R^2b, R^2c, R^2d, R^3e and R¹⁴ are hydrogen, J¹ and J² are Chb, L is a bond and A is 2-oxo-1 ,3-oxazolidin-3-yl;

except for the compound I wherein Z¹ is 4-chlorophenyl, Z² is 2,4,6- trifluorophenyl, Q is Q-1 , X is CR^3e, R^1a, R^1b, R^2a, R^2b, R^2c, R^2d, R^3e and R¹⁴ are hydrogen, J¹ and J² are Chb, L is a bond and A is 2-oxo-1 ,3-oxazolidin-3-yl; except for compounds I wherein Z¹ and Z² are phenyl substituted with 1 , 2 or 3 radicals selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl and Ci-C6-alkoxy; Q is Q-1 , X is CR^3e, R^1a, R¹ , R^2a, R² , R^2c, R^2d, R^3e and R¹⁴ are hydrogen, J¹ and J² are Chb, L is a bond and A is methylcarbonyloxy (-0-C(0)-CH3) or methyl- sulfonyloxy (-0-S(0)2-CH₃);

and

except for compounds I wherein Z² is 2-furanyl, Q is Q-1 , X is N, R^1a, R^1b, R^2a, R^2b, R^2c, R^2d and R¹⁴ are hydrogen, J¹ and J² are CH₂, L is a bond, A is hydrogen and Z¹ is phenyl, 3'-fluorobiphenyl-4-yl, 4'-fluorobiphenyl-4-yl or 4'- methoxybi phenyl-4-yl .

2. The compounds as claimed in claim 1 , where Q is a radical of formula Q-1. 3. The compounds as claimed in any of the preceding claims, where X is CR^3e.

4. The compounds as claimed in claim 3, where CR^3e is selected from hydrogen, halogen and Ci-C6-alkyl, and is in particular hydrogen. 5. The compounds as claimed in any of the preceding claims, where L is selected from a single bond, Ci-Ci2-alkylene, Ci-Ci2-haloalkylene, C2-Cio-alkenylene and C2-Cio-haloalkenylene, and in particular from a single bond, Ci-Ci2-alkylene and Ci-Ci2-haloalkylene. 6. The compounds as claimed in claim 5, where L is a single bond.

7. The compounds as claimed in any of the preceding claims, where A is a group A1 selected from -CR^d=N-R^c , -C(=N-N(R^c )R^c2)R^d and -C(=NR^c )N(R^c2)R^c3. 8. The compounds as claimed in claim 7, where A1 is -CR^d=N-R^c1.

9. The compounds as claimed in claim 8, where R^c1 is selected from Ci-C6-alkyl, Cs-Cs-cycloalkyI and Ci-C6-alkoxy, wherein the aliphatic and cycloaliphatic moie- ties in the 3 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁸;

phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy.

10. The compounds as claimed in claim 9, where R^c1 is selected from Ci-C6-alkyl, Cs-Cs-cycloalkyI and Ci-C6-alkoxy, wherein the aliphatic and cycloaliphatic moieties in the 3 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁸; and is in particular Ci-C6-alkoxy, wherein the aliphatic moiety in this radical may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁸.

1 1 . The compounds as claimed in claim 8, where R^c1 is selected from hydroxyl, Ci- C6-alkoxy, C2-C6-alkenyloxy and C2-C6-alkynyloxy, wherein the aliphatic moieties in the 3 last-mentioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents R¹⁸.

12. The compounds as claimed in any of claims 9 to 1 1 , where R¹⁸ is selected from 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, Cs-Cs-cycloalkyI, Cs-Cs-halocycloalkyl, where the cycloaliphatic moieties in the two last-mentioned radicals may be substituted by one or more cyano radicals; Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, phenyl which may carry 1 , 2 or 3 radicals selected from halogen, cyano, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy; and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, S, O, NO, SO and SO2 and optionally also 1 or 2 groups C(=0) or C(=S) as ring members, where the heterocyclic ring may be substituted by 1 , 2 or 3 radicals selected from halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy; and as a substituent on a cycloalkyl moiety, R¹⁸ is additionally selected from

Ci-C4-alkyl and Ci-C4-haloalkyl.

The compounds as claimed in claim 7, where A1 is -C(=N-N(R^c1)R^c2)R^d.

14. The compounds as claimed in claim 13, where R^c1 is selected from -C(=0)R^b, -C(=0)NR^b R^b2, -C(=S)R^b and -C(=S)NR R ².

15. The compounds as claimed in claim 14, where R^b is selected from Ci-C6-alkyl and Ci-C6-haloalkyl, and R^b1 and R^b2, independently of each other, are selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl. 16. The compounds as claimed in any of claims 7 to 15, where R^c2 and R^d, independently of each other, are selected from hydrogen, Ci-C6-alkyl and C1-C6- haloalkyl.

17. The compounds as claimed in any of claims 1 to 6, where A is a group A2.

18. The compounds as claimed in claim 17, where L is a single bond and A2 is OR a

19. The compounds as claimed in claim 18, where R^a is selected from hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the aliphatic and cycloaliphatic moieties in the 4 aforementioned radicals may be partially or fully halogenated and/or may carry 1 or 2 substituents selected from Ci-C4-alkoxy and oxo and in particular from Ci-C4-alkoxy; phenyl, benzyl and pyridyl, wherein the four last-mentioned radicals may carry one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Ci-C6-alkoxycarbonyl; and is in particular selected from Ci-C6-alkyl which may carry 1 oxo substituent, and Ci-C6-haloalkyl.

20. The compounds as claimed in claim 17, where L is a single bond, X is N, J¹ and J² are -C(=0)-, and A2 is Ci-C₆-alkyl.

21 . The compounds as claimed in any of the preceding claims, where R^2a, R^2b, R^2c and R^2d are hydrogen.

22. The compounds as claimed in any of claims 1 to 19 and 21 , where J¹ is - C(R^3aR³ )- and J² is -C(R^3cR^3d)-.

23. The compounds as claimed in claim 22, where R^3a, R^3b, R^3c and R^3d are

independently selected from hydrogen, halogen and Ci-C4-alkyl, and are in particular hydrogen.

24. The compounds as claimed in any of the preceding claims, where R^1a and R^1b are hydrogen.

25. The compounds as claimed in any of the preceding claims, where Z¹ is selected from phenyl which may carry 1 , 2, 3, 4 or 5 radicals R^4a; and pyridyl which may carry 1 , 2 or 3 radicals R^4a; and Z² is selected from phenyl which may carry 1 , 2, 3, 4 or 5 radicals R^4b; and pyridyl which may carry 1 , 2 or 3 radicals R^4b.

26. The compounds as claimed in claim 25, where Z¹ is selected from phenyl which may carry 1 , 2 or 3 radicals R^4a; and 2-pyridyl which may carry 1 , 2 or 3 radicals R^4a; and Z² is selected from phenyl which may carry 1 , 2 or 3 radicals R^4b; and 2-pyridyl which may carry 1 , 2 or 3 radicals R^4b.

27. The compounds as claimed in any of claims 25 or 26, where each R^4a and each R^4b is independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and in particular from halogen, methyl and trifluo- romethoxy.

28. A method for preparing compounds of formula I, which method comprises reacting a compound of formula II, wherein Z¹, Z², R^1a, R^{1 b} and R¹⁴ are as defined in claim 1 and Y is a leaving group, and Q-H, wherein Q is a radical of formula Q-1 , Q-2, Q-3 or Q-4 as defined in claim 1 and the hydrogen atom H is bound to the nitrogen ring atom of Q that, in formula I, forms the attachment point of the reR^1aR^{1 b}

(I I)

29. A method for preparing compounds of formula I wherein R^{1 b} is hydrogen, which method comprises subjecting a compound of formula III, wherein Z¹, Z², R^1a and

R¹⁴ are as defined in claim 1 , to a reductive amination with Q-H, wherein Q is a radical of formula Q-1 , Q-2, Q-3 or Q-4 as defined in claim 1 and the hydrogen atom H is bound to the nitrogen ring atom of Q that, in formula I, forms the attachment point of the respective radical of formula Q-1 , Q-2, Q-3 or Q-4 to CR^1aR¹

(III)

30. An agricultural or veterinary composition comprising at least one compound of the formula I, as defined in any of claims 1 to 27, 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.

31 . The use of a compound as defined in any of claims 1 to 27, of a stereoisomer and/or of an agriculturally or veterinarily acceptable salt thereof for combating invertebrate pests.

32. The use of a compound as defined in any of claims 1 to 27, of a stereoisomer and/or of a veterinarily acceptable salt thereof, for treating or protecting an animal from infestation or infection by invertebrate pests.

33. 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 27, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof. 34. The method as claimed in claim 33, 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 formula I as defined in any of claims 1 to 27, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.

35. The method as claimed in claim 34, for protecting plant propagation material and/or the plants which grow therefrom from attack or infestation by invertebrate pests, which method comprises treating the plant propagation material with a pesticidally effective amount of at least one compound of the formula I as defined in any of claims 1 to 27, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof. 36. Plant propagation material, comprising at least one compound of the formula I as defined in any of claims 1 to 27, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.

37. A method for treating or protecting an animal from infestation or infection by in- vertebrate 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 27, a stereoisomer thereof and/or at least one veterinarily acceptable salt thereof.