WO2015158605A1

WO2015158605A1 - Hetaryl substituted malononitrile compounds

Info

Publication number: WO2015158605A1
Application number: PCT/EP2015/057741
Authority: WO
Inventors: Sebastian SÖRGEL; Pascal BINDSCHÄDLER; Matthias Pohlman; Ralph Paulini; Christopher Palmer; Takeo Hokama
Original assignee: Basf Se
Priority date: 2014-04-16
Filing date: 2015-04-09
Publication date: 2015-10-22

Abstract

The invention relates to the use of a compound of formula (I) or a salt thereof for combating animal pests, where the symbols and indices are defined in the specification.

Description

Hetaryl substituted malononitrile compounds Description The invention relates to aryl alkyl malononitriles, thioamides and amides, a method for their preparation and their use for combating animal pests, an agricultural composition or seeds comprising said malononitriles, thioamides or amides, a method for combating animal pests, a method for protecting crops from attack or infestation by animal pests, a method for protecting seeds from soil insects and the seedlings' roots and shoots from soil and foliar insects.

Animal pests destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and to property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for combating animal pests. In particular, animal pests such as insects and acaridae are difficult to be effectively controlled. However, it is a continuing objective to provide further pesticidal compounds which, at least in some aspects, offer advantages over the known compounds.

Pesticidal compounds having a dicyanoalkane moiety have been disclosed in a number of pa- tent applications, e.g. JP 2002 284608, WO 02/089579, WO 02/090320, WO 02/090321 , WO 04/006677, WO 04/020399, JP 2004 99593, JP 2004 99597, WO 05/068432, WO 05/064823, EP 1555259, WO 05/063694, WO 2007/071609, and WO 2007/147888.

It has now been found that particular aryl alkyl malononitriles, thioamides and amides bearing an additional 5-membered aromatic heterocyclic ring on the aforementioned alkyl group are particularly useful for controlling pests, in particular invertebrate pests.

Accordingly, in one aspect of the invention there is provided the use of a compound of formula

(I)

or a salt thereof for combating animal pests, wherein

Y is phenyl unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituents R⁵; or naphthyl un- substituted or substituted with 1 , 2, 3, 4, 5, 6 or 7 substituents R⁵;

Q is a 5-membered aromatic heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from N, O, S, wherein the aforementioned ring is unsubstituted or substituted with 1 , 2, 3 or 4 substituents R⁶; R¹ is hydrogen, halogen, cyano, hydroxy, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8- cycloalkyl, Cs-Cs-cycloalkenyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, Ci-C6-alkylthio, (C1-C6- alkoxy)carbonyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with 1 , 2 or 3 substituents R⁷;

R² is hydrogen or halogen; or

R¹ and R² form together with the carbon atom to which they are attached a methylene group or a cyclopropyl group;

R³ is hydrogen, halogen, cyano, hydroxy, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8- cycloalkyl, Cs-Cs-cycloalkenyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, Ci-C6-alkylthio, (C1-C6- alkoxy)carbonyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with 1 , 2 or 3 substituents R⁷;

R⁴ is hydrogen or halogen; or

R³ and R⁴ form together with the carbon atom to which they are attached a methylene group or a cyclopropyl group; each R⁵, R⁶ is independently halogen, cyano, azido, nitro, -SCN, SF₅, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, wherein the carbon atoms of the aforementioned aliphatic radicals are unsubstituted or substituted with one or more R^a;

C3-C8 cycloalkyi or C3-C8 cycloalkenyl, wherein the carbon atoms of the aforementioned cycloaliphatic radicals are unsubstituted or substituted with one or more R^b;

phenyl unsubstituted or substituted with up to 5 R^c;

a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring con- taining 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R^d;

Si(R^e)₃, OR^f, SR^f, OS(0)_xR^h, S(0)_xR^h, Ν(^)₂, N(Rⁱ)C(=0)R^m, OC(=0)R^m, C(=0)R^m, C(=0)OR^f, C(=NR')R^m, C(=S)R^m;

or

two R⁵ on two adjacent carbon atoms present on one phenyl ring form together with the carbon atoms the two R⁵ are bonded to a 5- or 6-membered partially unsaturated carbocyclic ring or a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring containing 1 or 2 heteroatoms selected from N, O, S, wherein the aforementioned carbocyclic or heterocyclic ring is unsubstituted or substituted with 1 or 2 substituents selected from =0, OH, CH3, OCH3, halogen, halomethyl and halomethoxy;

or

two R⁶ on two adjacent atoms present on one 5-membered aromatic heterocyclic ring form together with the atoms the two R⁶ are bonded to a 5- or 6-membered partially unsaturated or aromatic carbocyclic ring or a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O, S, wherein the aforementioned carbocyclic or heterocyclic ring is unsubstituted or substituted with 1 or 2 substituents selected from =0, CH3, OCH3, halogen, halomethyl and halomethoxy; each R⁷ is independently halogen, cyano, hydroxy, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, d-d-cycloalkenyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, Ci-C6-alkylthio, (d-d- alkoxy)carbonyl, OSi(R^e)3, wherein the carbon atoms of the aforementioned aliphatic or cycloal- iphatic radicals are unsubstituted, partially or fully halogenated and/or oxygenated;

R^aa is -C(=S)N(R^CC)₂, -C(=NR^dd)SR^ee, -C(=0)N(R^ff)₂, or CN;

R^bb is -C(=S)N(R^CC)₂, -C(=NR^dd)SR^ee, -C(=0)N(R^ff)₂, or CN; each R^cc is independently hydrogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C₂-C6-alkenyl, C₂- C6-haloalkenyl, C₂-C6-alkynyl, C₂-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, d-d- alkoxy-d-d-alkyl, Ci-C₆-haloalkoxy-Ci-C₆-alkyl, Ci-C₆-alkylthio-Ci-C₆-alkyl, d-d- haloalkylthio-Ci-Ce-alkyl; each R^dd is independently hydrogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C₂-C6-alkenyl, C₂- C6-haloalkenyl, C₂-C6-alkynyl, C₂-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, d-d- alkoxy-d-d-alkyl, Ci-C₆-haloalkoxy-Ci-C₆-alkyl, Ci-C₆-alkylthio-Ci-C₆-alkyl, d-d- haloalkylthio-Ci-Ce-alkyl; each R^ee is independently cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C₂-C6-alkenyl, d-d- haloalkenyl, C₂-C6-alkynyl, C₂-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, d-d- alkoxy-d-d-alkyl, Ci-C₆-haloalkoxy-Ci-C₆-alkyl, Ci-C₆-alkylthio-Ci-C₆-alkyl, d-d- haloalkylthio-Ci-Ce-alkyl; each R^ff is independently hydrogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C₂-C6-alkenyl, C₂- C6-haloalkenyl, C₂-C6-alkynyl, C₂-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, d-d- alkoxy-d-d-alkyl, Ci-C₆-haloalkoxy-Ci-C₆-alkyl, Ci-C₆-alkylthio-Ci-C₆-alkyl, d-d- haloalkylthio-Ci-Ce-alkyl; each R^a is independently halogen, cyano, azido, nitro, -SCN, SF₅, d-d-alkyl, d-d- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, d-d- alkylsulfonyl, Ci-d-haloalkylthio, d-d-cycloalkyl, d-d-halocycloalkyl, d-d-alkenyl, d-d- haloalkenyl, d-d-alkynyl, d-d haloalkynyl, Ci-d-alkyl-d-d-cycloalkyl,

Si(R^e)₃, OR^A, SR^A, OS0₂R^B, S(0)_xR^B, -S(0)_xN(R^D)₂, N(R^D)₂, C(=0)N(R^D)₂, C(=S)N(R^D)₂, C(=0)OR^A,

phenyl unsubstituted or substituted with up to 5 R^E; a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R^E,

or

two R^a present on one carbon atom are together =0, =C(R^F)₂, =NR^D, =NOR^A, =NN(R^D)₂, or

two R^a form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring together with the carbon atoms the two R^a are bonded to; each R^b is independently halogen, cyano, azido, nitro, -SCN, SF₅, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, Ci-C6-alkyl-C3-C8-cycloalkyl,

Si(R^G)₃, OR^H, SR^H, OS0₂R^J, S(0)_xR^J, -S(0)_xN(R^K)₂, N(R^K)₂, C(=0)N(R^K)₂, C(=S)N(R^K)₂, C(=0)OR^H,

or

two R^b present on one carbon atom are together =0, =C(R^L)₂, =NR^K, =NOR^H, =NN(R^K)₂, or

two R^b form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring together with the carbon atoms the two R^b are bonded to; each R^c is independently halogen, cyano, azido, nitro, -SCN, SF₅, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R^M;

Si(R^G)₃, 0R^H, SR^H, OS(0)_xR^J, S(0)_xR^J, -S(0)_xN(R^K)₂, N(R^K)₂, C(=0)R^N, C(=0)OR^H, C(=NR^K)R^N, C(=0)N(R^K)₂, C(=S)N(R^K)₂; each R^d is independently halogen, cyano, azido, nitro, -SCN, SF₅, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R^M;

Si(R^G)₃, 0R^H, SR^H, OS(0)_xR^J, S(0)_xR^J, -S(0)_xN(R^K)₂, N(R^K)₂, C(=0)R^N, C(=0)OR^H, C(=NR^K)R^N, C(=0)N(R^K)₂, C(=S)N(R^K)₂,

or

two R^d present on one atom of a saturated or partially unsaturated heterocyclic ring are together =0, =C(R^L)₂; =NR^K, =NOR^H or =NN(R^K)₂; each R^e is independently halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C8 cycloalkyi, C3-C8 halocycloal- kyl, C1-C6 haloalkoxyalkyl,

phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, S0₂; each R^f is independently hydrogen, cyano, Ci-C6-alkyl, Ci-C6-alkylsulfinyl, C1-C6- alkylsulfonyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R^M;

Si(R^e)₃, S(0)xR^B, -S(0)xN(R^D)₂, N(R^D)₂, -N=C(R^F)₂, C(=0)R«, C(=0)N(R^D)₂, C(=S)N(R^D)₂, C(=0)OR^A,

phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, S0₂; each R^h is independently hydrogen, cyano, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Cs-Cs- cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R^M;

N(R^D)₂, -N=C(R^F)₂, C(=0)R^Q, C(=0)N(R^D)₂, C(=S)N(R^D)₂, C(=0)OR^A,

phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, S0₂; each R' is independently hydrogen, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C3-C8- cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R^M;

S(0)xR^B, -S(0)xN(R^D)₂, C(=0)R^s, C(=0)OR^A, C(=0)N(R^D)₂, C(=S)R^S, C(=S)SR^A, C(=S)N(R^D)₂, C(=NR^D)R^S,

phenyl unsubstituted or substituted with up to 5 R^E;

a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R^E,

or

two R' on one nitrogen atom are together a C2-C7 alkylene chain and form together with the ni- trogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or aromatic ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, and wherein the alkylene chain is unsubstituted or substituted with halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl; each R^m is independently hydrogen, -SCN, SF₅, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R^M;

Si(R^e)₃, OR^A, SR^A, OS0₂R^B, N(R^D)₂, C(=0)N(R^D)₂, C(=S)N(R^D)₂, C(=0)OR^A,

phenyl unsubstituted or substituted with up to 5 R^E;

a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R^E; each R^A is independently hydrogen, cyano, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, trime- thylsilyl, triethylsilyl, tert-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyI, wherein the four last mentioned radi- cals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy;

phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy and (Ci-C6-alkoxy)carbonyl; each R^B is independently hydrogen, cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyI, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radi- cals selected from C1-C4 alkoxy;

phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy and (Ci-C6-alkoxy)carbonyl; each R^D is independently hydrogen, cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert- butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyI, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radi- cals selected from Ci-C4-alkoxy;

phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy and (Ci-C6-alkoxy)carbonyl,

or

two R^D on one nitrogen atom are together a C2-C6 alkylene chain and form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, or 7-membered saturated, partially unsaturated or aromatic ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, and wherein the alkylene chain is unsubstituted or substituted with halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy; each R^E is independently cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert- butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last mentioned radicals are unsubsti- tuted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from Ci-C4-alkoxy,

or two R^E present on one atom of a saturated or partially unsaturated heterocyclic ring are together =0, =N(Ci-C₆-alkyl), =NO(Ci-C₆-alkyl), =CH(Ci-C₄-alkyl) or

each R^F is independently C1-C4 alkyl, C1-C6 cycloalkyl, C1-C4 alkoxyalkyl, phenyl or benzyl; each R^G is independently halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 haloalkoxyalkyl; each R^H is independently hydrogen, cyano, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, trime- thylsilyl, triethylsilyl, tert-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last mentioned radicals are unsub- stituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy; each R^J is independently hydrogen, cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last mentioned radicals are unsub- stituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy; each R^K is independently hydrogen, cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert- butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last mentioned radicals are unsub- stituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from Ci-C₄-alkoxy; each R^L is independently Ci-C₄ alkyl or Ci-C₄ alkoxyalkyl; each R^M is independently halogen, cyano, azido, nitro, OH, SH, -SCN, SF₅, Ci-C6-alkoxy, Ci- C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Ci-C6-alkyl-C3-C8-cycloalkyl, wherein the five last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygen- ated and/or carry 1 or 2 radicals selected from Ci-C₄ alkoxy,

or

two R^M present on one carbon atom are together =0, =CH(Ci-C₄-alkyl), =C(Ci-C₄-alkyl)Ci-C₄- alkyl, =N(Ci-C₆-alkyl) or =NO(Ci-C₆-alkyl); each R^N is independently hydrogen, OH, SH, -SCN, SF₅, Ci-C₆-alkoxy, Ci-C₆-haloalkoxy, Ci- C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last mentioned radicals are unsub- stituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy; each R^Q is independently hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert- butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radi- cals selected from C1-C4 alkoxy;

phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy and (Ci-C6-alkoxy)carbonyl; each R^s is independently hydrogen, OH, SH, -SCN, SF₅, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci- C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,

phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, (Ci-C6-alkoxy)carbonyl, (Ci-C6-alkyl)amino and di- (Ci-C6-alkyl)amino; p is O or l ; x is 1 or 2. Compounds of this type are disclosed in e.g. EP 0445698 and JP 05059003.

In a further aspect of the invention there is provided an agricultural and/or veterinary composition comprising at least one compound of formula (I) according to the invention or a salt thereof. In a preferred embodiment said composition further comprises at least one inert liquid and/or at least one solid carrier.

In yet a further aspect of the invention there is provided a method for combating animal pests, which comprises contacting the animal pests, their habit, breeding ground, food supply, plant, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one compound of formula (I) according to the invention or a salt thereof. In a further aspect of the invention there is provided a method for protecting crops from attack or infestation by animal pests, which comprises contacting the crop with a pesticidally effective amount of at least one compound of formula (I) according to the invention or a salt thereof. In yet a further aspect of the invention there is provided a method for protecting seeds from soil insects and the seedlings' roots and shoots from soil and foliar insects, which comprises contacting the seeds before sowing and/or after pregermination with at least one compound of formula (I) according to the invention or a salt thereof. In a further aspect of the invention there are provided seeds comprising at least one compound of formula (I) according to the invention or a salt thereof.

In yet a further aspect of the invention there is provided the use of a compound of formula (I) according to the invention or a salt thereof for combating parasites in and on animals.

In a further aspect of the invention there is provided a method for treating or protecting animals against infestation or infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of at least one compound of formula (I) according to the invention or a salt thereof.

In yet a further aspect of the invention there is provided a method for the preparation of a composition for treating or protecting animals against infestation or infection by parasites, which comprises mixing a parasiticidally effective amount of at least one compound of formula (I) according to the invention or a salt thereof and at least one solid carrier.

In a further aspect of the invention there is provided the use of a compound of formula (I) according to the invention or a salt thereof for the preparation of a medicament for treating or protecting animals against infestation or infection by parasites. In yet a further aspect of the invention there is provided a compound of formula (I) according to the invention or a salt thereof, with the proviso that R^cc is H when R^aa or R^bb is CN.

In a further aspect of the invention there is provided a compound of formula (I) according to the invention or a salt thereof as a medicament.

The present invention also relates to plant propagation materials, in particular seeds, comprising at least one compound of formula I or a salt thereof.

The present invention relates to every possible stereoisomer of the compounds of formula I, i.e. to single enantiomers or diastereomers, as well as to mixtures thereof.

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

Salts of the compounds of formula I are preferably agriculturally and/or veterinarily acceptable salts. They can be formed in a customary manner, 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 or veterinarily useful 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 ions of the alkali metals, preferably lithium, sodium and potassium, of the alka- line 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, di- methylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetrae- thylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl- ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammo- nium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.

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

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.

In case the 5-membered aromatic heterocyclic ring Q contains at least one nitrogen atom as a ring member, the aforementioned ring may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.

In case the 5-membered aromatic heterocyclic ring Q contains at least one nitrogen atom as a ring member, and in case the aforementioned ring is substituted with at least one substituent R⁶, the aforementioned substituent(s) may be attached to a carbon ring member or to a nitrogen ring member.

In case the 5-membered aromatic heterocyclic ring Q contains at least one nitrogen atom as a ring member, and in case a substituent R⁶ is attached to a nitrogen ring member, the aforementioned substituent is preferably Ci-C4-alkyl, more preferably CH3.

In case Q is pyrrolyl, imidazolyl, pyrazolyl, triazolyl or tetrazolyl, the aforementioned ring may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.

In case Q is pyrrolyl, imidazolyl, pyrazolyl, triazolyl or tetrazolyl, and in case the aforementioned ring is substituted with at least one substituent R⁶, the aforementioned substituent(s) may be attached to a carbon ring member or to a nitrogen ring member.

In case Q is pyrrolyl, imidazolyl, pyrazolyl, triazolyl or tetrazolyl, and in case a substituent R⁶ is attached to a nitrogen ring member, the aforementioned substituent is preferably Ci-C4-alkyl, more preferably CH3. The term "two R⁵ on two adjacent carbon atoms present on one phenyl ring form together with the carbon atoms the two R⁵ are bonded to a 5- or 6-membered partially unsaturated carbocyclic ring or a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring containing 1 or 2 heteroatoms selected from N, O, S, wherein the aforementioned carbocyclic or heterocyclic ring is unsubstituted or substituted with 1 or 2 substituents selected from =0, OH, CH3, OCH3, halogen, halomethyl and halomethoxy" preferably means "two R⁵ on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from CH2CH2CH2CH2, N=CH- CH=CH, CH=N-CH=CH, N=CH-N=CH, N=CH-CH=N, OCH₂CH₂CH₂, OCH=CHCH₂,

CH2OCH2CH2, OCH2CH2O, OCH2OCH2, CH2CH2CH2, CH=CHCH₂, CH2CH2O, CH=CHO, CH2OCH2, 0(CH₂)0, SCH2CH2CH2, SCH=CHCH₂, CH₂SCH₂CH₂, SCH₂CH₂S, SCH₂SCH₂, CH2CH2S, CH=CHS, CH2SCH2, CH₂C(=S)S, C(=S)SCH₂, S(CH₂)S, CH₂CH₂NR^K, CH₂CH=N, CH=CH-NR^K, OCH=N, SCH=N and form together with the carbon atoms the two R⁵ are bonded to a 5- or 6-membered partially unsaturated or aromatic carbocyclic or heterocyclic ring, wherein the ring is unsubstituted or substituted with 1 or 2 substituents selected from =0, OH, CH3, OCH3, halogen, halomethyl and halomethoxy".

The term "two R⁶ on two adjacent atoms present on one 5-membered aromatic heterocyclic ring form together with the atoms the two R⁶ are bonded to a 5- or 6-membered partially unsaturated or aromatic carbocyclic ring or a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O, S, wherein the aforementioned carbocyclic or heterocyclic ring is unsubstituted or substituted with 1 or 2 substituents selected from =0, CH3, OCH3, halogen, halomethyl and halomethoxy" preferably means "two R⁶ on two adjacent atoms present on one 5-membered aromatic heterocyclic ring are together a bridge selected from CH=CH-CH=CH, CH2CH2CH2CH2, N=CH-CH=CH, CH=N-CH=CH, N=CH-N=CH, N=CH-CH=N, OCH2CH2CH2, CH2OCH2CH2, OCH2CH2O, OCH2OCH2, CH2CH2CH2, CH=CHCH₂, CH2CH2O, CH=CHO, CH₂OCH₂, 0(CH₂)0, SCH₂CH₂CH₂, CH₂SCH₂CH₂,

CH₂CH₂NR^K, CH₂CH=N, CH=CH-NR^K, OCH=N, SCH=N and form together with the atoms the two R⁶ are bonded to a 5- or 6-membered partially unsaturated or aromatic carbocyclic or het- erocyclic ring, wherein the ring is unsubstituted or substituted with 1 or 2 substituents selected from =0, CH3, OCH3, halogen, halomethyl and halomethoxy".

In case the 5-membered aromatic heterocyclic ring Q contains at least one nitrogen atom as a ring member, the term "two adjacent atoms" used in the context of "two R⁶ on two adjacent at- oms present on one 5-membered aromatic heterocyclic ring" may comprise two carbon atoms that are adjacent to each other or one carbon atom and one nitrogen atom that are adjacent to each other.

The term "halogen" as used herein refers to fluoro, chloro, bromo and iodo.

The term "partially or fully halogenated" as used herein means that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine. The term "C_n-C_m-alkyl" as used herein (and also in e.g. C_n-C_m-alkylamino, di-C_n-C_m-alkylamino, Cn-Cm-alkylaminocarbonyl, di-(C_n-C_m-alkylamino)carbonyl, C_n-C_m-alkylthio, C_n-C_m-alkylsulfinyl and Cn-Cm-alkylsulfonyl) refers to a branched or unbranched saturated hydrocarbon group having n to m, e.g. 1 to 10 carbon atoms, preferably 1 to 6 or 1 to 4 carbon atoms, for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, hexyl, 1 ,1 - dimethylpropyl, 1 ,2-dimethylpropyl, 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, 1 -ethyl-2-methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers. Ci-C4-alkyl means for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl or 1 ,1 -dimethylethyl.

The term "C_n-C_m-haloalkyl" as used herein (and also in e.g. C_n-C_m-haloalkylsulfinyl and C_n-C_m- haloalkylsulfonyl) refers to a straight-chain or branched alkyl group having n to m carbon atoms, e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example Ci-C4-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichlorome- thyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlo- rodifluoromethyl, 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, pentafluoroethyl and the like. The terms Ci-Cio-haloalkyl, Ci-C6-haloalkyl or Ci-C4-haloalkyl in particular comprise Ci-C2-fluoroalkyl, which is synonym with methyl or ethyl, wherein 1 , 2, 3, 4 or 5 hydrogen atoms are substituted by fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoromethyl.

Similarly, the terms "C_n-C_m-alkoxy" and "C_n-C_m-alkylthio" (or the term "C_n-C_m-alkylsulfenyl", re- spectively) refer to straight-chain or branched alkyl groups having n to m carbon atoms, e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as mentioned above) bonded through oxygen or sulfur linkages, respectively, at any bond in the alkyl group. Examples include Ci-C4-alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy, futher Ci-C4-alkylthio such as methylthio, ethylthio, propylthio, isopropylthio, and n-butylthio.

Accordingly, the terms "C_n-C_m-haloalkoxy" and "C_n-C_m-haloalkylthio" (or the term "C_n-C_m- haloalkylsulfenyl", respectively) refer to straight-chain or branched alkyl groups having n to m carbon atoms, e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as mentioned above) bonded through oxygen or sulfur linkages, respectively, at any bond in the alkyl group, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example Ci-C2-haloalkoxy, such as chloromethoxy, bromomethoxy, dichloro- methoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluorometh- oxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1 -chloroethoxy, 1 -bromoethoxy, 1 -fluoro- ethoxy, 2-fluoroethoxy, 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 and pentafluoroeth- oxy, further Ci-C2-haloalkylthio, such as chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethyl- thio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1 -chloroethylthio, 1 -bromoethylthio, 1 - fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoro- ethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio and pentafluoroethylthio and the like. Similarly the terms "Ci-C2-fluoroalkoxy" and "Ci-C2-fluoro- alkylthio" refer to Ci-C2-fluoroalkyl which is bound to the remainder of the molecule via an oxygen atom or a sulfur atom, respectively. The term "C2-C_m-alkenyl" as used herein refers to a branched or unbranched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2 to 6 or 2 to 4 carbon atoms and a double bond in any position, such as ethenyl, 1 -propenyl, 2-propenyl, 1 -methyl-ethenyl, 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 and 1 -ethyl-2-methyl-2- propenyl.

The term "C2-C_m-alkynyl" as used herein refers to a branched or unbranched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2 to 6 or 2 to 4 carbon atoms and containing at least one triple bond, such as ethynyl, propynyl, 1 -butynyl, 2-butynyl and the like.

The term "Ci-C4-alkoxy-Ci-C4-alkyl" as used herein refers to alkyl having 1 to 4 carbon atoms, e.g. like specific examples mentioned above, wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkoxy group. The term "C3-C_m-cycloalkyl" as used herein refers to a monocyclic 3- to m-membered saturated cycloaliphatic radical, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooc- tyl and cyclodecyl.

The term "aryl" as used herein refers to an aromatic hydrocarbon radical such as naphthyl or in particular phenyl.

The term "naphthyl" as used herein refers to 1 -naphthyl and 2-naphthyl. Preferably, naphthyl is 2-naphthyl. The term "3- to 6-membered carbocyclic ring" as used herein refers to cyclopropane, cyclobu- tane, cyclopentane and cyclohexane rings.

The term "3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2" as used herein refers to monocyclic radicals, the monocyclic radicals being saturated, partially unsaturated or aromatic. The heterocyclic radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.

Examples of 3-, 4-, 5-, 6- or 7-membered saturated heterocyclyl include:

oxiranyl, aziridinyl, azetidinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3- tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2- imidazolidinyl, 4-imidazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 3-isoxazolidinyl, 4- isoxazolidinyl, 5-isoxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 3-isothiazolidinyl, 4- isothiazolidinyl, 5-isothiazolidinyl, 1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4-oxadiazolidin-5-yl, 1 ,2,4-thiadi- azolidin-3-yl, 1 ,2,4-thiadiazolidin-5-yl, 1 ,2,4-triazolidin-3-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4- thiadiazolidin-2-yl, 1 ,3,4-triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 1 ,3-dioxan-5- yl, 1 ,4-dioxan-2-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-hexahydropyridazinyl, 4- hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2- piperazinyl, 1 ,3,5-hexahydrotriazin-2-yl and 1 ,2,4-hexahydrotriazin-3-yl, 2-morpholinyl, 3- morpholinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 1 -oxothiomorpholin-2-yl, 1 -oxothiomorpholin-

3- yl, 1 ,1 -dioxothiomorpholin-2-yl, 1 ,1 -dioxothiomorpholin-3-yl, hexahydroazepin-1 -, -2-, -3- or -4- yl, hexahydrooxepinyl, hexahydro-1 ,3-diazepinyl, hexahydro-1 ,4-diazepinyl, hexahydro-1 ,3- oxazepinyl, hexahydro-1 ,4-oxazepinyl, hexahydro-1 ,3-dioxepinyl, hexahydro-1 ,4-dioxepinyl and the like.

Examples of 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclyl include:

2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien- 2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-

3- yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin 3 yl, 2-iso- xazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin- 5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-

4- yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3- dihydropyrazol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1 -yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4- yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1 -yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol- 4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol- 4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4 di- or tetrahydro- pyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5 di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1 ,3,5-di- or tetrahydrotriazin-2-yl, 1 ,2, 4-di- or tetrahydrotriazin- 3-yl, 2,3,4,5-tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin- 2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7- tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydrooxepinyl, such as 2,3,4,5-tetra- hydro[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, tetrahy- dro-1 ,4-diazepinyl, tetrahydro-1 ,3-oxazepinyl, tetrahydro-1 ,4-oxazepinyl, tetrahydro-1 ,3- dioxepinyl and tetrahydro-1 ,4-dioxepinyl.

3-, 4-, 5-, 6- or 7-membered aromatic heterocyclyl is 5- or 6-membered aromatic heterocyclyl (hetaryl). Examples are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4- pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2- imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4- pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.

The term "C2-C7-alkylene" as used herein refers to a divalent branched or preferably un- branched saturated aliphatic chain having 2 to 7 carbon atoms, for example CH2CH2,

-CH(CHs)-, CH2CH2CH2, CH(CH₃)CH₂, CH₂CH(CH₃), CH2CH2CH2CH2, CH2CH2CH2CH2CH2, CH2CH2CH2CH2CH2CH2 and CH2CH2CH2CH2CH2CH2CH2. The term "tri-(Ci-C4-alkyl)silyl-C2-C4-alkynyl" as used herein refers to C2-C4-alkynyl substituted with tri-(Ci-C4-alkyl)silyl. The term "(trimethylsilyl)ethynyl" as used herein refers to ethynyl substituted with trimethylsilyl. The term "Ci-C6-alkyl-C3-C8-cycloalkyl" as used herein refers to Cs-Cs-cycloalkyl substituted with Ci-C6-alkyl. The term "Ci-C4-alkyl-C3-C6-cycloalkyl" as used herein refers to C3-C6- cycloalkyl substituted with Ci-C4-alkyl.

Preferably, the term "phenyl unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituents R⁵ / R⁶" means "phenyl unsubstituted or substituted with up to 3 or in the case of halogen up to the maximum possible number of substituents R⁵ / R⁶", and also preferably "phenyl unsubstituted or substituted with 1 , 2, 3 or 4 substituents R⁵ / R⁶", more preferably "phenyl unsubstituted or substituted with 1 , 2 or 3 substituents R⁵ / R⁶", even more preferably "phenyl unsubstituted or substituted with 1 or 2 substituents R⁵ / R⁶", and particularly preferably "phenyl unsubstituted or substituted with 1 substituent R⁵ / R⁶".

Preferably, the term "naphthyl unsubstituted or substituted with 1 , 2, 3, 4, 5, 6 or 7 substituents R⁵" means "naphthyl unsubstituted or substituted with up to 3 or in the case of halogen up to the maximum possible number of substituents R⁵", more preferably "naphthyl unsubstituted or sub- stituted with up to 3 substituents R⁵", even more preferably "naphthyl unsubstituted or substituted with up to 2 substituents R⁵", and particularly preferably "naphthyl unsubstituted or substituted with up to 1 substituent R⁵".

Preferably, the term "unsubstituted or substituted with up to 5 R^c / R^d / R^E, e.g. in connection with phenyl or a heterocyclic ring, means "unsubstituted or substituted with up to 3 or in the case of halogen up to the maximum possible number of R^c / R^d / R^E", more preferably "unsubstituted or substituted with up to 2 or in the case of halogen up to the maximum possible number of R^c / R^d / R^E", also more preferably "unsubstituted or substituted with up to 3 R^c / R^d / R^E", and even more preferably "unsubstituted or substituted with up to 2 R^c / R^d / R^E".

Preferably, the term "unsubstituted or substituted with one or more", e.g. in connection with substituents R⁶, R^a, R^b or R^M, means "unsubstituted or substituted with up to 5 or in the case of halogen up to the maximum possible number of", more preferably "unsubstituted or substituted with up to 3 or in the case of halogen up to the maximum possible number of", even more pref- erably "unsubstituted or substituted with up to 2 or in the case of halogen up to the maximum possible number of", also more preferably "unsubstituted or substituted with up to 5", also even more preferably "unsubstituted or substituted with up to 3", and particularly preferably "unsubstituted or substituted with up to 2". The preferred, more preferred, even more preferred and particularly preferred substituents and embodiments described herein are to be understood as preferred either independently of each other or in every possible combination with each other. These preferences and embodiments apply to the compounds of the invention, to the use of the compounds of the invention as well as to methods using the compounds of the invention.

Preferred are compounds of formula (I) wherein Y is phenyl unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituents R⁵; or naphthyl unsubstituted or substituted with 1 or 2 substituents R⁵.

Preferred are compounds of formula (I) wherein Q is a 5-membered aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O, S, wherein the aforementioned ring is unsubstituted or substituted with 1 , 2 or 3 substituents R⁶.

Preferred are compounds of formula (I) wherein R¹ is H, halogen, cyano, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or (Ci-C6-alkoxy)carbonyl,

wherein the five radicals last mentioned are unsubstituted or substituted with 1 , 2 or 3 substituents selected from halogen, cyano, hydroxy, OSi(Ci-C6-alkyl)3, Ci-C6-alkyl, C2-C6-alkenyl, C2- C6-alkynyl, C3-C6-cycloalkyl, Ci-C6-alkoxy and (Ci-C6-alkoxy)carbonyl,

wherein the six radicals last mentioned are unsubstituted or partially or fully halogenated;

and in particular the ones wherein R¹ is H, Me, Et, iPr, cPr, CH₂CN, CF₃, CHF₂, CH₂F,

CH2CH2F, CH2CHF2, CH2CF3, CN, halogen, CH₂OH, CH₂OMe, CH₂OEt, C0₂Me, C0₂Et, CH₂C0₂Me, CH₂C0₂Et, CH₂OSi(Me)₃ or CH₂OSi(Et)₃.

Preferred are compounds of formula (I) wherein R² is H or halogen.

Also preferred are compounds of formula (I) wherein R¹ and R² form together with the carbon atom to which they are attached a methylene group.

Preferred are compounds of formula (I) wherein R³ is H, halogen, cyano, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or (Ci-C6-alkoxy)carbonyl,

and in particular the ones wherein R³ is H, Me, Et, iPr, cPr, CH₂CN, CF₃, CHF₂, CH₂F,

Preferred are compounds of formula (I) wherein R⁴ is H or halogen.

Also preferred are compounds of formula (I) wherein R³ and R⁴ form together with the carbon atom to which they are attached a methylene group.

Preferred are compounds of formula (I) wherein R⁵ is halogen, cyano, SF₅, tri-(Ci-C4-alkyl)silyl- C2-C4-alkynyl, (Ci-C6-alkyl)aminocarbonyl, di-(Ci-C6-alkyl)aminocarbonyl, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, (Ci-C6-alkoxy)carbonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl or (Ci-C6-alkyl)carbonyloxy,

wherein the 14 radicals last mentioned are unsubstituted or substituted with one or more (particularly up to 3 or in the case of halogen up to the maximum possible number) substituents se- lected from halogen, cyano, Ci-C4-alkyl-C3-C6-cycloalkyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl and Ci-C6-alkoxy,

wherein the five radicals last mentioned are unsubstituted or partially or fully halogenated; or

two R⁵ on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from N=CH-CH=CH, N=CH-CH=N, OCH2CH2O, 0(CH₂)0 and form together with the carbon atoms the two R⁵ are bonded to a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring, wherein the ring is unsubstituted;

and in particular the ones wherein R⁵ is halogen (particularly F, CI, Br), Me, Et, iPr, cPr, OMe, OEt, OiPr, ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, CN, CF₃, OCF₃, SF₅, CHF₂, OCHF₂, SMe, S(0)Me, S(0)₂Me, SCF₃, S(0)CF₃, S(0)₂CF₃, SCHF₂, S(0)CHF₂, S(0)₂CHF₂, C0₂Me, C0₂Et, C(0)Me, OAc, C(0)NHMe, C(0)NMe₂, CH₂OMe or CH₂OEt;

or

two R⁵ on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from N=CH-CH=CH, N=CH-CH=N, OCH2CH2O, 0(CH₂)0 and form together with the carbon atoms the two R⁵ are bonded to a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring, wherein the ring is unsubstituted.

Also preferred are compounds of formula (I) wherein R⁵ is halogen, cyano, SF₅, tri-(Ci-C4- a I kyl )si lyl-C2-C4-a I kynyl , (Ci-C6-alkyl)aminocarbonyl, di-(Ci-C6-alkyl)aminocarbonyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, (Ci-C6-alkoxy)carbonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl or (Ci-C6-alkyl)carbonyloxy,

wherein the five radicals last mentioned are unsubstituted or partially or fully halogenated; and in particular the ones wherein R⁵ is halogen (particularly F, CI, Br), Me, Et, iPr, cPr, OMe, OEt, OiPr, ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, CN, CF₃, OCF₃, SF₅, CHF₂, OCHF₂, SMe, S(0)Me, S(0)₂Me, SCF₃, S(0)CF₃, S(0)₂CF₃, SCHF₂, S(0)CHF₂, S(0)₂CHF₂, C0₂Me, C0₂Et, C(0)Me, OAc, C(0)NHMe, C(0)NMe₂, CH₂OMe or CH₂OEt.

Preferred are compounds of formula (I) wherein R⁶ is halogen, nitro, cyano, SF₅, tri-(Ci-C4- a I kyl )si lyl-C2-C4-a I kynyl , 2,2,2-trifluoro-1 -hydroxy-1-(trifluoromethyl)ethyl, (C1-C6- alkyl)aminocarbonyl, di-(Ci-C6-alkyl)aminocarbonyl, dimethylcarbamoylsulfanyl, morpholine-4- carbonyl, acetamido, pyridyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, C3-C6-alkynyloxy, C3-C6-cycloalkoxy, phe- noxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, (Ci-C6-alkoxy)carbonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl or (Ci-C6-alkyl)carbonyloxy, wherein the 17 radicals last mentioned are unsubstituted or substituted with one or more (particularly up to 3 or in the case of halogen up to the maximum possible number) substituents se- lected from halogen, cyano, Ci-C4-alkyl-C3-C6-cycloalkyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl and Ci-C6-alkoxy,

two R⁶ on two adjacent atoms present on one 5-membered aromatic heterocyclic ring are to- gether a bridge selected from CH=CH-CH=CH, N=CH-CH=CH, N=CH-CH=N, OCH2CH2O, 0(CH2)0 and form together with the atoms the two R⁶ are bonded to a 5- or 6-membered partially unsaturated or aromatic carbocyclic or heterocyclic ring, wherein the ring is unsubstituted; and in particular the ones wherein R⁶ is halogen (particularly F, CI, Br), Me, Et, iPr, cPr, tBu, OMe, OEt, OiPr, OtBu, ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, N0₂, CN, CF₃, OCF₃, SF₅, CHF₂, OCHF2, SMe, S(0)Me, S(0)₂Me, SCF₃, S(0)CF₃, S(0)₂CF₃, SCHF₂, S(0)CHF₂,

S(0)₂CHF₂, C0₂Me, C0₂Et, C0₂iPr, C(0)Me, OAc, C(0)NHMe, C(0)NMe₂, CH₂OMe, CH₂OEt, 2,2,2-trifluoroethyl, 1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl, 2,2,2-trifluoro-1 -hydroxy-1 - (trifluoromethyl)ethyl, dimethoxymethyl, 2,2,2-trifluoroethoxy, 2,2-difluorocyclopropoxy, tert- butylsulfanyl, dimethylcarbamoylsulfanyl, morpholine-4-carbonyl, acetamido or prop-2-ynoxy; or

two R⁶ on two adjacent atoms present on one 5-membered aromatic heterocyclic ring are together a bridge selected from CH=CH-CH=CH and form together with the atoms the two R⁶ are bonded to a 6-membered aromatic carbocyclic or heterocyclic ring, wherein the ring is unsubstituted.

Also preferred are compounds of formula (I) wherein R⁶ is halogen, nitro, cyano, SF₅, tri-(Ci-C4- a I kyl )si lyl-C2-C4-a I kynyl , 2, 2, 2-trifluoro-1 -hydroxy-1 -(trifluoromethyl)ethyl, (C1-C6- alkyl)aminocarbonyl, di-(Ci-C6-alkyl)aminocarbonyl, dimethylcarbamoylsulfanyl, morpholine-4- carbonyl, acetamido, pyridyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, C3-C6-alkynyloxy, C3-C6-cycloalkoxy, phe- noxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, (Ci-C6-alkoxy)carbonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl or (Ci-C6-alkyl)carbonyloxy, wherein the 17 radicals last mentioned are unsubstituted or substituted with one or more (particularly up to 3 or in the case of halogen up to the maximum possible number) substituents se- lected from halogen, cyano, Ci-C4-alkyl-C3-C6-cycloalkyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl and Ci-C6-alkoxy,

wherein the five radicals last mentioned are unsubstituted or partially or fully halogenated; and in particular the ones wherein R⁶ is halogen (particularly F, CI, Br), Me, Et, iPr, cPr, tBu, OMe, OEt, OiPr, OtBu, ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, N0₂, CN, CF₃, OCF₃, SF₅, CHF₂, OCHF2, SMe, S(0)Me, S(0)₂Me, SCF₃, S(0)CF₃, S(0)₂CF₃, SCHF₂, S(0)CHF₂,

S(0)₂CHF₂, C0₂Me, C0₂Et, C0₂iPr, C(0)Me, OAc, C(0)NHMe, C(0)NMe₂, CH₂OMe, CH₂OEt, 2,2,2-trifluoroethyl, 1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl, 2,2,2-trifluoro-1 -hydroxy-1 - (trifluoromethyl)ethyl, dimethoxymethyl, 2,2,2-trifluoroethoxy, 2,2-difluorocyclopropoxy, tert- butylsulfanyl, dimethylcarbamoylsulfanyl, morpholine-4-carbonyl, acetamido or prop-2-ynoxy.

Preferred are compounds of formula (I) wherein R^aa is -C(=S)N(R^CC)₂, -C(=0)N(R^ff)₂, or CN.

Preferred are compounds of formula (I) wherein R^bb is CN.

Preferred are compounds of formula (I) wherein each R^cc is independently hydrogen, C1-C4- alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl or Ci-C4-alkoxy-Ci-C2-alkyl.

Preferred are compounds of formula (I) wherein each R^ff is independently hydrogen, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl or Ci-C4-alkoxy-Ci-C2-alkyl.

Also preferred are compounds of formula (I) wherein R^aa is -C(=S)N(R^CC)₂, -C(=0)N(R^ff)₂, or CN; each R^cc is independently hydrogen, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl or Ci-C4-alkoxy-Ci-C2-alkyl; and each R^ff is independently hydrogen, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl or Ci-C4-alkoxy-Ci-C2-alkyl.

Preferred are compounds of formula (I) wherein p is 0 or 1 , and in particular the ones wherein p is 0.

More preferred are compounds of formula (I) wherein Y is phenyl unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituents R⁵; or naphthyl unsubstituted or substituted with 1 substituent R⁵.

More preferred are compounds of formula (I) wherein Q is pyrrolyl, furanyl, thiophenyl, imidazol- yl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl or thiadiazolyl, wherein the aforementioned rings are unsubstituted or substituted with 1 , 2 or 3 substituents R⁶. More preferred are compounds of formula (I) wherein R¹ is H, Me, Et, CN, CH2CN, CH2CF3, halogen, CH₂OH, CH₂OMe, CH₂OEt, CH₂C0₂Me, CH₂C0₂Et, CH₂OSi(Me)₃ or CH₂OSi(Et)₃.

More preferred are compounds of formula (I) wherein R² is H or halogen. More preferred are compounds of formula (I) wherein R³ is H, Me, Et, CN, CH2CN, CH2CF3, halogen, CH₂OH, CH₂OMe, CH₂OEt, CH₂C0₂Me, CH₂C0₂Et, CH₂OSi(Me)₃ or CH₂OSi(Et)₃.

More preferred are compounds of formula (I) wherein R⁴ is H or halogen. More preferred are compounds of formula (I) wherein R⁵ is halogen, cyano, tri-(Ci -C -a I kyl ) si lyl- C2-C4-alkynyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, Ci-C6-alkylthio or (Ci-C6-alkoxy)carbonyl,

wherein the eight radicals last mentioned are unsubstituted or partially or fully halogenated; or

two R⁵ on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from N=CH-CH=CH, N=CH-CH=N, OCH₂CH₂0, 0(CH₂)0 and form together with the carbon atoms the two R⁵ are bonded to a 5- or 6-membered partially unsaturated or aromatic heterocy- die ring, wherein the ring is unsubstituted.

Also more preferred are compounds of formula (I) wherein R⁵ is halogen, cyano, tri-(Ci-C4- alkyl)silyl-C2-C4-alkynyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, Ci- C6-alkoxy, Ci-C6-alkylthio or (Ci-C6-alkoxy)carbonyl,

wherein the eight radicals last mentioned are unsubstituted or partially or fully halogenated; and in particular the ones wherein R⁵ is halogen (particularly CI, F, Br), Me, OMe, CN, CF3, OCF3 or ethynyl.

More preferred are compounds of formula (I) wherein R⁶ is halogen, nitro, cyano, tri-(Ci-C4- a I kyl )si lyl-C2-C4-a I kynyl , 2,2,2-trifluoro-1 -hydroxy-1-(trifluoromethyl)ethyl, dimethoxymethyl, di- methylcarbamoylsulfanyl, morpholine-4-carbonyl, acetamido, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, C3-C6-alkynyloxy, C3-C6-cycloalkoxy, phenoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfonyl or (Ci-C6-alkoxy)carbonyl,

wherein the twelve radicals last mentioned are unsubstituted or partially or fully halogenated; or

Also more preferred are compounds of formula (I) wherein R⁶ is halogen, nitro, cyano, tri-(Ci- C4-alkyl)silyl-C2-C4-alkynyl, 2,2,2-trifluoro-1 -hydroxy-1 -(trifluoromethyl)ethyl, dimethoxymethyl, dimethylcarbamoylsulfanyl, morpholine-4-carbonyl, acetamido, Ci-C6-alkyl, C2-C6-alkenyl, C2- C6-alkynyl, C3-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, C3-C6-alkynyloxy, C3-C6-cycloalkoxy, phenoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfonyl or (Ci-C6-alkoxy)carbonyl,

wherein the twelve radicals last mentioned are unsubstituted or partially or fully halogenated; and in particular the ones wherein R⁶ is halogen (particularly CI, F, Br), Me, OMe, CN, CF3, OCF3, ethynyl or prop-2-ynoxy. More preferred are compounds of formula (I) wherein R^aa is

or CN.

More preferred are compounds of formula (I) wherein R^bb is CN.

More preferred are compounds of formula (I) wherein each R^cc is independently H, Me, Et, pro- pargyl, allyl, CH₂OMe or CH₂OEt.

Also more preferred are compounds of formula (I) wherein R^aa is

or CN; and each R^cc is independently H, Me, Et, propargyl, allyl, CH₂OMe or CH₂OEt. More preferred are compounds of formula (I) wherein p is 0 or 1 , and in particular the ones wherein p is 0. Even more preferred are compounds of formula (I) wherein Y is phenyl unsubstituted or substituted with 1 , 2 or 3 substituents R⁵.

Even more preferred are compounds of formula (I) wherein Q is pyrrolyl, furanyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl or thiadia- zolyl, wherein the aforementioned rings are unsubstituted or substituted with 1 or 2 substituents R⁶.

Even more preferred are compounds of formula (I) wherein R¹ is H, F, Me, Et, CN, ChbCN or ChbOMe, and in particular the ones wherein R¹ is H.

Even more preferred are compounds of formula (I) wherein R² is H.

Even more preferred are compounds of formula (I) wherein R⁵ is F, CI, Br or CF3. Even more preferred are compounds of formula (I) wherein R⁶ is F, ethynyl, prop-2-ynoxy or CF₃.

Even more preferred are compounds of formula (I) wherein R^aa is -C(=S)NH2 or CN. Even more preferred are compounds of formula (I) wherein R^bb is CN. Even more preferred are compounds of formula (I) wherein p is 0.

Also preferred are compounds of formula (I) wherein all symbols and indices have the preferred meanings.

Also more preferred are compounds of formula (I) wherein all symbols and indices have the more preferred meanings. Also even more preferred are compounds of formula (I) wherein all symbols and indices have the even more preferred meanings.

Preferred are compounds of formula (I) wherein

Y is phenyl unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituents R⁵; or naphthyl un- substituted or substituted with 1 or 2 substituents R⁵;

Q is a 5-membered aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O, S, wherein the aforementioned ring is unsubstituted or substituted with 1 , 2 or 3 substituents R⁶; R¹ is H, halogen, cyano, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or (C1-C6- alkoxy)carbonyl,

wherein the five radicals last mentioned are unsubstituted or substituted with 1 , 2 or 3 substitu- ents selected from halogen, cyano, hydroxy, OSi(Ci-C6-alkyl)3, Ci-C6-alkyl, C2-C6-alkenyl, C2- C6-alkynyl, C3-C6-cycloalkyl, Ci-C6-alkoxy and (Ci-C6-alkoxy)carbonyl,

R² is H or halogen;

or

R¹ and R² form together with the carbon atom to which they are attached a methylene group; R³ is H, halogen, cyano, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or (C1-C6- alkoxy)carbonyl,

R⁴ is H or halogen;

or

R³ and R⁴ form together with the carbon atom to which they are attached a methylene group; R⁵ is halogen, cyano, SF₅, tri-(Ci-C4-alkyl)silyl-C2-C4-alkynyl, (Ci-C6-alkyl)aminocarbonyl, di- (Ci-C6-alkyl)aminocarbonyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, (Ci-C6-alkoxy)carbonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl or (Ci-C6-alkyl)carbonyloxy, wherein the 14 radicals last mentioned are unsubstituted or substituted with one or more sub- stituents selected from halogen, cyano, Ci-C4-alkyl-C3-C6-cycloalkyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl and Ci-C6-alkoxy,

R⁶ is halogen, nitro, cyano, SF₅, tri-(Ci-C4-alkyl)silyl-C2-C4-alkynyl, 2,2,2-trifluoro-1 -hydroxy- 1 -(trifluoromethyl)ethyl, (Ci-C6-alkyl)aminocarbonyl, di-(Ci-C6-alkyl)aminocarbonyl, dimethylcar- bamoylsulfanyl, morpholine-4-carbonyl, acetamido, pyridyl, pyrrolyl, pyrazolyl, imidazolyl, tria- zolyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, C3-C6- alkynyloxy, C3-C6-cycloalkoxy, phenoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, (Ci-C6-alkoxy)carbonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl or (Ci- C6-alkyl)carbonyloxy,

wherein the 17 radicals last mentioned are unsubstituted or substituted with one or more sub- stituents selected from halogen, cyano, Ci-C4-alkyl-C3-C6-cycloalkyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl and Ci-C6-alkoxy,

wherein the five radicals last mentioned are unsubstituted or partially or fully halogenated; or two R⁶ on two adjacent atoms present on one 5-membered aromatic heterocyclic ring are together a bridge selected from CH=CH-CH=CH, N=CH-CH=CH, N=CH-CH=N, OCH₂CH₂0, 0(CH2)0 and form together with the atoms the two R⁶ are bonded to a 5- or 6-membered partially unsaturated or aromatic carbocyclic or heterocyclic ring, wherein the ring is unsubstituted; R^aa is -C(=S)N(R^CC)₂, -C(=0)N(R^ff)₂, or CN;

R^bb is CN;

each R^cc is independently hydrogen, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6- cycloalkyl or Ci-C4-alkoxy-Ci-C2-alkyl;

each R^ff is independently hydrogen, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6- cycloalkyl or Ci-C4-alkoxy-Ci-C2-alkyl;

p is O or l .

More preferred are compounds of formula (I) wherein

Y is phenyl unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituents R⁵; or naphthyl un- substituted or substituted with 1 substituent R⁵;

Q is pyrrolyl, furanyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothia- zolyl, triazolyl, oxadiazolyl or thiadiazolyl, wherein the aforementioned rings are unsubstituted or substituted with 1 , 2 or 3 substituents R⁶;

R is H, Me, Et, CN, CH₂CN, CH2CF3, halogen, CH₂OH, CH₂OMe, CH₂OEt, CH₂C0₂Me, CH₂C0₂Et, CH₂OSi(Me)₃ or CH₂OSi(Et)₃;

R² is H or halogen;

R³ is H, Me, Et, CN, CH₂CN, CH2CF3, halogen, CH₂OH, CH₂OMe, CH₂OEt, CH₂C0₂Me, CH₂C0₂Et, CH₂OSi(Me)₃ or CH₂OSi(Et)₃;

R⁴ is H or halogen;

R⁵ is halogen, cyano, tri-(Ci-C4-alkyl)silyl-C2-C4-alkynyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, Ci-C6-alkylthio or (Ci-C6-alkoxy)carbonyl, wherein the eight radicals last mentioned are unsubstituted or partially or fully halogenated; or

R⁶ is halogen, nitro, cyano, tri-(Ci -C4-a I kyl )si lyl-C2-C4-a I ky ny 1 , 2,2,2-trifluoro-1 -hydroxy-1 - (trifluoromethyl)ethyl, dimethoxymethyl, dimethylcarbamoylsulfanyl, morpholine-4-carbonyl, ac- etamido, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, C3- C6-alkynyloxy, C3-C6-cycloalkoxy, phenoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfonyl or (C1-C6- alkoxy)carbonyl,

two R⁶ on two adjacent atoms present on one 5-membered aromatic heterocyclic ring are together a bridge selected from CH=CH-CH=CH and form together with the atoms the two R⁶ are bonded to a 6-membered aromatic carbocyclic or heterocyclic ring, wherein the ring is unsubstituted; R^aa is -C(=S)N(R^cc)₂ or CN;

R^bb is CN;

each R^cc is independently H, Me, Et, propargyl, allyl, CH₂OMe or CH₂OEt;

p is O or l .

Even more preferred are compounds of formula (I) wherein

Y is phenyl unsubstituted or substituted with 1 , 2 or 3 substituents R⁵;

Q is pyrrolyl, furanyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothia- zolyl, triazolyl, oxadiazolyl or thiadiazolyl, wherein the aforementioned rings are unsubstituted or substituted with 1 or 2 substituents R⁶;

R is H, F, Me, Et, CN, CH₂CN or CH₂OMe;

R⁵ is F, CI, Br or CF₃;

R⁶ is F, ethynyl, prop-2-ynoxy or CF3;

R^aa is -C(=S)NH₂ or CN;

R^bb is CN;

p is 0.

Particular preference is given to compounds of formula (I) wherein Y is 4-fluorophenyl, 3- fluorophenyl, 2-fluorophenyl, 4-chlorophenyl, 3-cyanophenyl, 4-bromophenyl, 3-methylphenyl, 3-methoxyphenyl, 4-trifluoromethylphenyl, 3,5-difluorophenyl or 3,4,5-trifluorophenyl. Very particular preference is given to compounds of formula (I) wherein Y is 4-fluorophenyl, 3,5- difluorophenyl or 3,4,5-trifluorophenyl. Particular preference is given to compounds of formula (I) wherein Q is thiophenyl unsubstituted or substituted with 1 or 2 substituents R⁶. Very particular preference is given to compounds of formula (I) wherein Q is thiophenyl unsubstituted or substituted with 1 substituent R⁶.

Particular preference is given to compounds of formula (I) wherein R¹ is H.

Particular preference is given to compounds of formula (I) wherein R² is H.

Particular preference is given to compounds of formula (I) wherein R¹ and R² are H.

Particular preference is given to compounds of formula (I) wherein R³ is H.

Particular preference is given to compounds of formula (I) wherein R⁴ is H.

Particular preference is given to compounds of formula (I) wherein R³ and R⁴ are H.

Particular preference is given to compounds of formula (I) wherein R¹, R², R³ and R⁴ are H.

Very particular preference is given to compounds of formula (I) wherein R¹ and R² are H; and p is 0.

In one embodiment R^cc is H when R^aa or R^bb is CN.

In a further embodiment R^cc is H. In a further embodiment R^ff is H. In a further embodiment R^cc is H; and R^ff is H.

In a preferred embodiment R^aa is -C(=S)NH₂, -C(=0)NH₂, or CN; and R^bb is CN.

In a more preferred embodiment R^aa is -C(=S)NH₂ or CN; and R^bb is CN.

In an even more preferred embodiment R^aa is CN; and R^bb is CN.

In another preferred embodiment R^aa is -C(=S)NH₂; and R^bb is CN.

In yet another preferred embodiment R^aa is -C(=S)NH₂ or -C(=0)NH₂; and R^bb is CN.

In another preferred embodiment R^aa is -C(=0)NH₂; and R^bb is CN. In yet another preferred embodiment R^aa is -C(=S)NH₂; and R^bb is -C(=S)NH₂.

In another preferred embodiment R^aa is -C(=0)NH₂; and R^bb is -C(=0)NH₂.

In one embodiment Q is pyrrolyl, furanyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl or tetrazolyl, wherein the aforementioned rings are unsubstituted or substituted with 1 , 2 or 3 substituents R⁶.

In one embodiment R¹ and R² do not form together with the carbon atom to which they are attached a methylene group. In a further embodiment R³ and R⁴ do not form together with the carbon atom to which they are attached a methylene group. In yet a further embodiment neither R¹ and R² nor R³ and R⁴ form together with the carbon atom to which they are attached a methylene group.

Further preferred compounds of formula (I) are compounds of formulae (la-1 ), (la-2), (la-3), (la- 4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) or (la-16),

(la-1 ) (la-2) (la-3) (la-4)

(la-5) (la-6) (la-7) (la-8)

wherein Y is phenyl substituted with 1 , 2, 3, 4 or 5 substituents R⁵; R^aa is -C(=S)NH₂ or CN; R^bb is CN; R¹ is H, F, Me, Et, CF₃, CN, CH₂OMe or CH₂CN; R² is H; p is 0; Q is as defined in formula (I); R^5a, R^5b, R^5c, R^5d and R^5e are as defined in table A.

The symbol "-" in any of columns R^5a, R^5b, R^5c, R^5d or R^5e in table A means that the phenyl ring does not carry a substituent R⁵ in the respective position, i.e. the phenyl ring carries an H in the respective position.

Table A













40

Table 1 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 1 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 2b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 2 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 3b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 3 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 4b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 4 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 5b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 5 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 6b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 6 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 7b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 7 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 8b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 8 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 9b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 9 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 10b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 10 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 1 1 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

1 1 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 12b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

12 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 13b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

13 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 14b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

14 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 15b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 15 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 16b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

16 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 17b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

17 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 18b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

18 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 19b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

19 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 20b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 20 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 21 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

21 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 22b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

22 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 23b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

23 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 24b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

24 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 25b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

25 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 26b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

26 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 27b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

27 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 28b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

28 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 29b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 29 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 30b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

30 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 31 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

31 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 32b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

32 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 33b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

33 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 34b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 34 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 35b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

35 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 36b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

36 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 37b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

37 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 38b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

38 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 39b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

39 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 40b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

40 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 41 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

41 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 42b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

42 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 43b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 43 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 44b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

44 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 45b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

45 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 46b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

46 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 47b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

47 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 48b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 48 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 49b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

49 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 50b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

50 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 51 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

51 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 52b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

52 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 53b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

53 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 54b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

54 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 55b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

55 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 56b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

56 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 57b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 57 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 58b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

58 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 59b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

59 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 60b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

60 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 61 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

61 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 62b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 62 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 63b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

63 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 64b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

64 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 65b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

65 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 66b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

66 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 67b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

67 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 68b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

68 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 69b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

69 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 70b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

70 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 71 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 71 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 72b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

72 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 73b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

73 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 74b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

74 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 75b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

75 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 76b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 76 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 77b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

77 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 78b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

78 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 79b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

79 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 80b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

80 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 81 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

81 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 82b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

82 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 83b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

83 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 84b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

84 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 85b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 85 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 86b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

86 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 87b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

87 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 88b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

88 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 89b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

89 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 90b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 90 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 91 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

91 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 92b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

92 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 93b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

93 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 94b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

94 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 95b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

95 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 96b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

96 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 97b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

97 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 98b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry

98 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 99b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-

9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 99 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 100b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 100 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 101 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 101 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 102b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 102 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 103b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 103 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 104b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 104 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 105b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 105 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 106b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 106 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 107b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 107 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 108b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 108 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 109b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 109 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 1 10b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 1 10 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 1 1 1 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 1 1 1 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 1 12b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 1 12 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 1 13b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 1 13 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 1 14b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 1 14 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 1 15b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 1 15 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 1 16b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 1 16 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 1 17b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 1 17 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 1 18b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 1 18 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 1 19b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 1 19 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 120b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 120 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 121 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 121 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 122b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 122 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 123b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 123 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 124b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 124 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 125b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 125 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 126b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 126 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 127b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 127 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 128b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 128 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 129b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 129 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 130b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 130 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 131 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 131 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 132b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 132 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 133b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 133 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 134b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 134 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 135b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 135 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 136b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 136 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 137b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 137 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 138b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 138 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 139b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 139 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 140b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 140 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 141 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 141 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 142b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 142 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 143b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 143 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 144b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 144 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 145b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 145 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 146b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 146 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 147b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 147 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 148b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 148 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 149b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 149 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 150b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 150 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 151 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 151 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 152b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 152 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 153b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 153 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 154b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 154 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 155b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 155 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 156b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 156 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 157b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 157 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 158b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 158 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 159b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 159 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 160b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 160 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 161 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 161 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 162b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 162 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 163b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 163 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 164b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 164 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 165b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 165 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 166b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 166 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 167b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 167 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 168b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 168 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 169b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 169 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 170b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 170 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 171 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 171 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 172b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 172 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 173b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 173 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 174b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 174 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 175b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 175 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 176b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 176 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 177b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 177 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 178b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 178 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 179b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 179 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 180b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 180 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 181 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 181 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 182b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 182 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 183b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 183 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 184b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 184 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 185b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 185 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 186b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 186 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 187b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 187 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 188b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 188 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 189b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 189 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 190b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 190 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 191 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 191 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 192b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 192 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 193b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 193 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 194b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 194 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 195b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 195 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 196b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 196 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 197b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 197 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 198b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 198 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 199b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 199 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 200b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 200 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 201 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 201 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 202b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 202 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 203b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 203 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 204b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 204 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 205b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 205 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 206b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 206 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 207b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 207 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 208b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 208 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 209b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 209 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 210b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 210 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 21 1 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 21 1 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 212b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 212 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 213b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 213 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 214b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 214 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 215b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 215 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 216b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 216 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 217b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 217 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 218b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 218 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 219b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 219 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 220b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 220 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 221 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 221 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 222b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 222 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 223b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 223 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 224b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 224 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 225b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 225 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 226b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 226 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 227b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 227 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 228b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 228 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 229b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 229 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 230b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 230 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 231 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 231 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 232b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 232 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 233b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 233 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 234b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 234 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 235b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 235 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 236b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 236 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 237b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 237 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 238b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 238 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 239b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 239 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 240b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 240 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 241 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 241 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 242b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 242 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 243b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 243 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 244b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 244 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 245b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 245 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 246b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 246 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 247b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 247 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 248b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 248 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 249b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 249 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 250b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 250 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 251 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 251 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 252b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 252 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 253b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 253 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 254b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 254 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 255b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 255 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 256b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 256 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 257b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 257 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 258b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 258 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 259b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 259 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 260b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 260 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 261 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 261 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 262b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 262 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 263b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 263 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 264b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 264 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 265b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 265 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 266b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 266 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 267b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 267 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 268b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 268 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 269b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 269 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 270b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 270 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 271 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 271 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 272b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 272 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 273b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 273 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 274b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 274 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 275b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 275 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 276b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 276 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 277b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 277 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 278b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 278 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 279b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 279 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 280b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 280 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 281 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 281 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 282b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 282 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 283b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 283 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 284b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 284 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 285b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 285 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 286b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 286 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 287b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 287 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 288b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 288 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 289b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 289 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 290b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 290 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 291 b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 291 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 292b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 292 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Table 293b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 293 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A. Table 294b: Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15) and (la-16), wherein Q is as defined in entry 294 of table B; and R^5a, R^5b, R^5c, R^5d and R^5e correspond in each case to a row of table A.

Particularly preferred compounds of formula (I) are compounds of formulae (la-1 ) or (la-2),

(la-1 ) (la-2) wherein Y is phenyl substituted with 1 , 2, 3, 4 or 5 substituents R⁵; R^aa is -C(=S)NH₂ or CN; R^bb is CN; R¹ is H; R² is H; p is 0; R^5a, R^5b, R^5c, R^5d and R^5e are as defined in table A; Q is as defined in tables 1 b to 294.

Preparation methods

The compounds of formula (I) according to the present invention can be prepared e.g. accord- ing to preparation methods and preparation schemes described below.

In the following schemes and methods, if not otherwise specified, the definition of the substituents, variables and indices in the formulae used correspond to the definitions given for formula (I) above.

Compounds of formula (I) can be prepared as shown in Scheme A below.

Scheme A.

(A) (B)

LG = leaving group if R^aa' is not R^aa or

(C) (I) if R^aa' is R^aa and

R^bb' is R^bb: (C) = (I)

Compounds of formula (A) are reacted with compounds of formula (B) in the presence of a suitable base to give compounds of formula (C). A representative procedure is described in e.g. M. M. Meyers, J. Sun, K. E. Carlson, G. A. Marriner, B. S. Katzenellenbogen, J. A. Katzenellenbogen, J. Med. Chem. 2001 , 44, 4230-4251. A further procedure is described in WO

2012/020130.

In the compounds of formula (C) R^aa' is R^aa or a precursor of R^aa, and R^bb' is R^bb or a precursor of R^bb. Compounds of formula (C) wherein R^aa' is R^aa, and wherein R^bb' is R^bb correspond to compounds of formula (I). Compounds of formula (C) wherein R^aa' is not R^aa, or wherein R^bb' is not R^bb represent synthetic intermediates, which can be further converted to compounds of formula (I). R^aa' in formula (A) generally corresponds to R^aa' in formula (C). Likewise, R^bb' in formula (A) generally corresponds to R^bb' in formula (C).

A suitable precursor of R^aa is, for example, -C(=0)0(Ci-C4-alkyl), such as -C(=0)OMe or -C(=0)OEt. A suitable precursor of R^bb is, for example, -C(=0)0(Ci-C4-alkyl), such as

-C(=0)OMe or -C(=0)OEt.

Compounds of formula (I) wherein R^aa is not CN are preferably prepared from compounds of formula (C) wherein R^aa' is a precursor of R^aa, for example, -C(=0)0(Ci-C4-alkyl), such as -C(=0)OMe or -C(=0)OEt. Compounds of formula (I) wherein R^bb is CN and wherein R^aa is not CN are preferably prepared from compounds of formula (C) wherein R^bb' is CN and wherein R^aa' is a precursor of R^aa, for example, -C(=0)0(Ci-C₄-alkyl), such as -C(=0)OMe or -C(=0)OEt. Compounds of formula (I) wherein R^bb is not CN are preferably prepared from compounds of formula (C) wherein R^bb' is a precursor of R^bb, for example, -C(=0)0(Ci-C₄-alkyl), such as -C(=0)OMe or -C(=0)OEt.

Compounds of formula (I) wherein R^aa is CN and wherein R^bb is not CN are preferably prepared from compounds of formula (C) wherein R^aa' is CN and wherein R^bb' is a precursor of R^bb, for example, -C(=0)0(Ci-C₄-alkyl), such as -C(=0)OMe or -C(=0)OEt.

Compounds of formula (I) wherein R^aa is not CN and wherein R^bb is not CN are preferably prepared from compounds of formula (C) wherein R^aa' is a precursor of R^aa, for example,

-C(=0)0(Ci-C₄-alkyl), such as -C(=0)OMe or -C(=0)OEt, and wherein R ' is a precursor of R^bb, for example, -C(=0)0(Ci-C₄-alkyl), such as -C(=0)OMe or -C(=0)OEt.

Compounds of formula (I) wherein R^aa is -C(=0)N(R^ff)2 and wherein R^bb is CN can, for example, be prepared from compounds of formula (C) wherein R^aa' is -C(=0)0(Ci-C₄-alkyl) and wherein R^bb' is CN by treatment with a suitable amine, NH(R^ff)2. In a particular embodiment of the invention, where R^ff is H, the amine is NH3.

Likewise, compounds of formula (I) wherein R^aa and R^bb are -C(=0)N(R^ff)2 can, for example, be prepared from compounds of formula (C) wherein R^aa' and R^bb' are -C(=0)0(Ci-C₄-alkyl) by treatment with a suitable amine, NH(R^ff)2. In a particular embodiment of the invention, where R^ff is H, the amine is NH3.

Compounds of formula (I) wherein R^aa is

and wherein R^bb is CN can, for example, be prepared from compounds of formula (C) wherein R^aa' is -C(=0)0(Ci-C₄-alkyl) and wherein R^bb' is CN by treatment with a suitable amine, NH(R^CC)2, followed by treatment of the resulting amide with e.g. P₄Sio or Lawesson's reagent to obtain the corresponding thioamide. In a particular embodiment of the invention, where R^cc is H, the amine is NH3.

Likewise, compounds of formula (I) wherein R^aa and R^bb are

can, for example, be prepared from compounds of formula (C) wherein R^aa' and R^bb' are -C(=0)0(Ci-C₄-alkyl) by treatment with a suitable amine, NH(R^CC)2, followed by treatment of the resulting amide with e.g. P₄Sio or Lawesson's reagent to obtain the corresponding thioamide. In a particular embodiment of the invention, where R^cc is H, the amine is NH3. Suitable functional group interconversions are described in e.g. WO 2003/99276; US 4740228; US 4304930; Journal of the American Chemical Society 1937, vol. 59, p. 1901 ; Synthesis 2004, p. 2625-2628; US 201 1/183960; WO 2008/1 10488; Journal of Medicinal Chemistry 1994, vol. 37, p. 371 -380; N. N. Dykhanov, Zhurnal Prikladnoi Khimii (Sankt Petersburg, Russian Federation) 1961 , 34, p. 1588-91 .

Compounds of formula (I) wherein R^aa and/or R^bb is -C(=NR^dd)SR^ee can, for example, be pre- pared from the corresponding thioamides by treatment with an alkylating agent.

Compounds of formula (I) wherein R^aa and R^bb are CN are generally prepared from compounds of formula (A) wherein R^aa' and R^bb' are CN. Accordingly, compounds of formula (I) wherein R^aa and R^bb are CN can be prepared as shown in Scheme B below.

Scheme B.

(I) wherein

R^aa and R^bb are CN

Compounds of formula (A) can be prepared by treatment of iodine compound A-1 with compound A-2 (Scheme C) as described in various publications. For example, this can be achieved in the presence of a base and a suitable palladium catalyst system as described in e.g. J. M. Atkins, S. A. Moteki, S. G. DiMagno, J. M. Takacs, Org. Lett. 2006, 13, 2759-2762. Alternatively, the reaction can also be carried out via copper catalysis in the presence of a base as described in e.g. M. Makosza, A. Chesnokov, Tetrahedron 2008, 64, 5925-5932. A further procedure is described in K. Okuro, M. Furuune, M. Miura, M. Nomura, Journal of Organic Chemistry 1993, 58(26), 7606-7. Scheme C. Y R^aa\ „R'

bb'

Y R

(A-1 ) (A-2) (A)

(A-1 ) (A-2) wherein (A) wherein

R^aa' and R^bb' are CN R^aa' and R^bb' are CN

Compounds of formula (B) with p = 0 like e.g. (B-5) in Scheme D that require a leaving group "LG" e.g. halogens or mesylates can be obtained starting from the respective halogenated com- pounds (B-1 ) as depicted below.

Scheme D.

(B-4) Reacting compounds of formula (B-1 ) with a lithium base followed by subsequent addition of DMF as described in e.g. WO 2012/0581 16 thus yields compounds of formula (B-2) which after reduction with e.g. a hydride reagent such as sodium borohydride yield (B-3) as described e.g. in WO 2012/022681 . Alternatively, compounds of formula (B-1 ) can also be treated with aldehydes e.g. acetaldehyde after reaction with a lithium base to directly yield compounds of formula (B-4) as described in e.g. Y. Zhang, J. P. Burgess, M. Brackeen, A. Gilliam, S. W. Mascarella, K. Page, H. H.

Seltzman, B. F. Thomas, J. Med. Chem. 2008, 51 , 3526-3539. Furthermore, various nucleo- philes can be reacted with intermediates of formula (B-2) to yield mono- or disubstituted alco- hols of formula (B-4) as described in e.g. J. A. Malona, K. Cariou, W. T. Spencer III, A. J. Frontier, J. Org. Chem. 2012, 77, 1891 -1908.

Compounds of formula (B-3) or (B-4) can be converted into compounds of formula (B-5) by means of activating the hydroxyl group e.g. via mesylation or tosylation as described in WO 2012/085645. Alternatively, they can be treated with phosphortribromide to convert the hydroxyl group into the respective bromide as described in WO 2012/022487.

Compounds of formula (B) with p = 1 like e.g. (B-6), (B-1 1 ), (B-12) or (B15) can be obtained starting from the respective carboxylic acid derivatives of formula (B-7), (B-9) or (B-13) as depicted in Schemes E to G. a-Alkylation can be employed to introduce R³ and R⁴ substituents as described in e.g. WO 2012/058134. Substituents R¹ and R² can be introduced, for example, by treatment of compounds of formula (B-8), (B-9), (B-10) or (B-14) with e.g. hydride reagents or Grignard reagents as described in e.g. A. K. Ghosh, C. D. Martyr, C.-X. Xu, Org. Lett. 2012, 14, 2002-2005.

Scheme E.

(B-7) (B-8) (B-6)

Scheme F.

H

N(Oalkyl)alkyl

o

(B-12)

Scheme G.

X = Oalkyl, N(Oalkyl)alkyl

The alcohols of formula (B-6), (B-1 1 ), (B-12) or (B15) can be further activated by similar methods as described above. lodo compounds of formula (A-1 ), chloro, bromo or iodo compounds of formula (B-1 ) as well as carboxylic acid derivatives needed for compounds of formula (B-7), (B-9) or (B-13) can be purchased or synthesized according to known literature methods. As a rule, the compounds of formula (I) can be prepared by the methods described above. If individual compounds cannot be prepared via the above-described routes, they can be prepared by derivatization of other compounds (I) or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds (I) can advantageously be prepared from other compounds (I) by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like.

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 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 with an appropriate solvent.

In a particular embodiment, where R^aa is -C(=S)NH₂ or -C(=0)NH₂ and where R^bb is CN, the compounds of formula (I) can, for example, be prepared according to the sequence illustrated in Scheme H. Scheme H.

catalyst C0₂Et

In a particular embodiment, where R^aa and R^bb are -C(=S)NH2 or where R^aa and R^bb are - C(=0)NH2, the compounds of formula (I) can, for example, be prepared according to the quence illustrated in Scheme J.

Scheme J.

catalyst Y C0₂Et

Compounds of formula (I) wherein R^aa is -C(=S)NH₂ and wherein R^bb is -C(=S)NH₂ or CN can, for example, be prepared from the corresponding dinitrile compounds by treatment with H₂S as illustrated in Scheme K. The reaction is preferably carried out in the presence of a base. Preferred bases include triethylamine, trimethylamine, N-ethyldiisopropylamine, triisopropylamine, ammonia, pyridine, lutidine, collidine, 4-(dimethylamino)pyridine (DMAP), imidazole, 1 ,8- diazabicyclo[5.4.0]undec-7-ene (DBU) or 1 ,5-diazabicyclo[4.3.0]non-5-ene (DBN). The reaction is preferably carried out in a solvent. Preferred solvents include dimethylformamide, dimethyla- cetamide, sulfolane, N-methylpyrrolidinone, 1 ,3-dimethylimazolidinone, dimethyl sulfoxide, water, dichloromethane, toluene, benzene, dioxane or mixtures thereof. H₂S can be used as a gas Alternatively, H₂S can be used as a solution.

Scheme K.

In a further aspect of the invention there is provided a method for preparing a compound of formula (I) according to the invention or a salt thereof, wherein R^aa is -C(=0)N(R^ff)2; and R^bb is -C(=0)N(R^ff)₂ or CN; or wherein R^aa is -C(=S)N(R^CC)₂; and R is -C(=S)N(R^CC)₂ or CN; comprising the steps of

(i) reacting a compound of formula (XI),

R^d

(XI)

bb*

Y R wherein Y is defined as in formula (I);

R^aa* is -C(=0)0(Ci-C₄-alkyl);

R ^* is -C(=0)0(Ci-C₄-alkyl) or CN,

provided that R^bb* is CN when R^bb is CN; with a compound of formula (XII),

wherein R¹, R², R³, R⁴, Q and p are defined as in formula (I);

L is a leaving group; optionally in the presence of a base, to obtain a compound of formula (XIII),

wherein R¹, R², R³, R⁴, Y, Q and p are defined as in formula (I);

R^aa* and R^bb* are defined as in formula (XI);

(ii) reacting the compound of formula (XIII) with an amine of formula (XIV),

NH(R^xx)₂ (XIV) wherein R^xx is R^cc or R^ff as defined in formula (I); to obtain a compound of formula (I), wherein R^aa is -C(=0)N(R^ff)₂; and R^bb is -C(=0)N(R^ff)₂ or CN; or a compound of formula (XV),

wherein R¹, R², R³, R⁴, Y, Q and p are defined as in formula (I);

R " is -C(=0)N(R^cc)₂ or CN,

wherein R^cc is defined as in formula (I);

(iii) converting the compound of formula (XV) to a compound of formula (I), wherein R^aa is - C(=S)N(R^CC)₂; and R^bb is -C(=S)N(R^CC)₂ or CN.

In one embodiment the reaction of the compound of formula (XI) with the compound of formula (XII) is carried out in the absence of a base.

In a preferred embodiment the reaction of the compound of formula (XI) with the compound of formula (XII) is carried out in the presence of a base.

Preferred, more preferred, even more preferred and particularly preferred compounds of formula (XI) are the ones leading to the respective preferred, more preferred, even more preferred and particularly preferred compounds of formula (I).

Preferred, more preferred, even more preferred and particularly preferred compounds of formula (XII) are the ones leading to the respective preferred, more preferred, even more preferred and particularly preferred compounds of formula (I). Preferred, more preferred, even more preferred and particularly preferred amines of formula

(XIV) are the ones leading to the respective preferred, more preferred, even more preferred and particularly preferred compounds of formula (I). In a particular preferred embodiment the amine of formula (XIV) is NH₃. Preference is given to compounds of formula (XII) wherein

L is halogen or OS(0)₂R^#; and

R^# is d-Ce-alkyl, Ci-C₆-haloalkyl, d-Ce-nitroalkyl, Ci-C₆-alkoxy-Ci-C₆-alkyl, C₃-C₆-cycloalkyl, phenyl or phenyl-Ci-C6-alkyl, wherein each phenyl is independently unsubstituted or substituted with up to 5 substituents selected from halogen, CN, N0₂, Ci-C6-alkyl, C1-C6- haloalkyl or Ci-C6-alkoxy.

Particular preference is given to compounds of formula (XII) wherein

L is CI, Br, I or OS(0)₂R^#; and

R^# is Ci-C6-alkyl, Ci-C6-haloalkyl or phenyl, wherein phenyl is unsubstituted or substituted with up to 5 substituents selected from halogen, N0₂, Ci-C6-alkyl or Ci-C6-alkoxy. Very particular preference is given to compounds of formula (XII) wherein

L is CI, Br or OS(0)₂R^*; and

R^# is Me, CF₃, C4F9, phenyl or toluyl.

The molar ratio of the compound of formula (XI) to the compound of formula (XII) is generally in the range of 1 :0.5-2, preferably in the range of 1 :0.5-1.5, more preferably in the range of 1 :0.8- 1 .2. Examples of suitable bases are carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, magnesium carbonate, calcium carbonate, barium carbonate; hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide, barium hydroxide, aluminum hy- droxide; oxides such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide, barium oxide, iron oxide, silver oxide; hydrides such as lithium hydride, sodium hydride, potassium hydride, calcium hydride; phosphates such as potassium phosphate, calcium phosphate; alkoxides such sodium, potassium or magnesium alkoxides; nitrogen-containing bases such as triethylamine, trimethylamine, N-ethyldiisopropylamine, triisopropylamine, am- monia, pyridine, lutidine, collidine, 4-(dimethylamino)pyridine (DMAP), imidazole, 1 ,8- diazabicyclo[5.4.0]undec-7-ene (DBU) or 1 ,5-diazabicyclo[4.3.0]non-5-ene (DBN), lithium hex- amethyldisilazide (LiHMDS), sodium hexamethyldisilazide (NaHMDS), potassium hexamethyl- disilazide (KHMDS), lithium diisopropylamide (LDA), lithium tetramethylpiperidide (LiTMP). Preferred bases include carbonates and hydrides. Particularly preferred bases include potassium carbonate, cesium carbonate and sodium hydride.

The term base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.

The molar ratio of the compound of formula (XI) to the base is generally in the range of 1 :0.8-3, preferably in the range of 1 :1 -2, more preferably in the range of 1 :1 -1.5.

Preferably, the reaction of the compound of formula (XI) with the compound of formula (XII) in the presence of a base is carried out in a solvent.

Examples of suitable solvents are dipolar aprotic solvents such as N,N-dimethylformamide (DMF), Ν,Ν-dimethylacetamide (DMAc), 1 -methyl-2-pyrrolidinone (NMP), 1 ,3-dimethyl-2- imidazolidinone (DMI), Ν,Ν'-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO), sul- folane, acetonitrile, benzonitrile, acetone, methyl ethyl ketone, methyl butyl ketone, methyl iso- butyl ketone, cyclohexanone, nitromethane, nitroethane, nitrobenzene; esters such as ethyl acetate, butyl acetate, isobutyl acetate; ethers such as diethylether, dibutylether, tert-butyl methyl ether (TBME), 1 ,2-dimethoxyethane, tetrahydrofurane (THF), cyclopentyl methyl ether, 1 ,4- dioxane; alcohols such as methanol, ethanol, isopropanol, 1 -butanol, 2-butanol, isobutanol, tert- butanol, hexafluoro isopropanol; halogenated hydrocarbons such as dichloromethane, dichloro- ethane, carbon tetrachloride; aliphatic hydrocarbons such as hexane, cyclohexane; aromatic hydrocarbons such as benzene, toluene, xylenes, mesitylene, chlorobenzene.

Preferred solvents include acetone, DMF, DMAc, 1 ,2-dimethoxyethane, DMI, dichloromethane, diethylether and THF. Particularly preferred solvents include acetone, 1 ,2-dimethoxyethane, diethylether and THF. The term solvent as used herein also includes mixtures of two or more of the above compounds.

The reaction of the compound of formula (XI) with the compound of formula (XII) in the presence of a base is generally carried out at a temperature in the range of from -40 to 80 °C, pref- erably in the range of from -20 to 40 °C, more preferably in the range of from 0 to 30 °C.

Step (ii) is preferably carried out in the presence of a solvent. Preferred solvents include methanol, ethanol, dichloromethane, THF, DMF, acetonitrile, toluene, benzene, ethyl acetate, dioxane, tert-butyl methyl ether, or mixtures thereof. Particular preference is given to alcohols such as methanol or ethanol.

Step (ii) is preferably carried out at a temperature in the range of from -40 to 80 °C, preferably in the range of from -20 to 40 °C, more preferably in the range of from 0 to 30 °C. Preferred reagents for converting the compound of formula (XV) to the compound of formula (I), wherein R^aa is -C(=S)N(R^CC)₂; and R^bb is -C(=S)N(R^CC)₂ or CN, include P4S10 and Lawesson's reagent. A particular preferred reagent for the use in step (iii) is P₄Sio. In one embodiment P₄Sio and hexamethyldisiloxane are used in step (iii). Step (iii) is preferably carried out in the presence of a solvent. Preferred solvents include dichloromethane, THF, DMF, acetonitrile, toluene, benzene, ethyl acetate, dioxane, tert-butyl methyl ether, or mixtures thereof. More preferred solvents include toluene, dichloromethane, or mixtures thereof. Particular preference is given to a toluene/dichloromethane mixture, wherein the ratio of toluene to dichloromethane (vohvol) is in the range of 2:1 to 1 :2, preferably 1.2:1 to 1 :1 .2, more preferably about 1 :1.

Step (iii) is preferably carried out at a temperature in the range of from 0 to 100 °C, preferably in the range of from 20 to 80 °C, more preferably in the range of from 50 to 70 °C. In yet a further aspect of the invention there is provided a method for preparing a compound of formula (I) according to the invention or a salt thereof, wherein R^aa is CN, and R^bb is CN, comprising the step of reacting a compound of formula (XXI),

wherein Y is defined as in formula (I); with a compound of formula (XXII),

wherein R¹, R², R³, R⁴, Q and p are defined as in formula (I); and

L is a leaving group; optionally in the presence of a base.

In one embodiment the reaction of the compound of formula (XXI) with the compound of formula (XXII) is carried out in the absence of a base.

In a preferred embodiment the reaction of the compound of formula (XXI) with the compound of formula (XXII) is carried out in the presence of a base. Preferred, more preferred, even more preferred and particularly preferred compounds of formula (XXI) are the ones leading to the respective preferred, more preferred, even more preferred and particularly preferred compounds of formula (I).

Preferred, more preferred, even more preferred and particularly preferred compounds of formu- la (XXII) are the ones leading to the respective preferred, more preferred, even more preferred and particularly preferred compounds of formula (I).

Preference is given to compounds of formula (XXII) wherein

L is halogen or OS(0)2R*; and

R^* is d-Ce-alkyl, Ci-C₆-haloalkyl, Ci-C₆-nitroalkyl, Ci-C₆-alkoxy-Ci-C₆-alkyl, C₃-C₆-cycloalkyl, phenyl or phenyl-Ci-C6-alkyl, wherein each phenyl is independently unsubstituted or substituted with up to 5 substituents selected from halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl or C1-C6- alkoxy. Particular preference is given to compounds of formula (XXII) wherein

L is CI, Br, I or OS(0)₂R^*; and

R^* is Ci-C6-alkyl, Ci-C6-haloalkyl or phenyl, wherein phenyl is unsubstituted or substituted with up to 5 substituents selected from halogen, NO2, Ci-C6-alkyl or Ci-C6-alkoxy. Very particular preference is given to compounds of formula (XXII) wherein

L is CI, Br or OS(0)₂R^*; and

R^* is Me, CF3, C4F9, phenyl or toluyl. The molar ratio of the compound of formula (XXI) to the compound of formula (XXII) is generally in the range of 1 :0.5-2, preferably in the range of 1 :0.5-1 .5, more preferably in the range of 1 :0.8-1.2.

Examples of suitable bases are carbonates such as lithium carbonate, sodium carbonate, po- tassium carbonate, cesium carbonate, magnesium carbonate, calcium carbonate, barium carbonate; hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide, barium hydroxide, aluminum hydroxide; oxides such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calci- urn oxide, barium oxide, iron oxide, silver oxide; hydrides such as lithium hydride, sodium hydride, potassium hydride, calcium hydride; phosphates such as potassium phosphate, calcium phosphate; alkoxides such sodium, potassium or magnesium alkoxides; nitrogen-containing bases such as triethylamine, trimethylamine, N-ethyldiisopropylamine, triisopropylamine, ammonia, pyridine, lutidine, collidine, 4-(dimethylamino)pyridine (DMAP), imidazole, 1 ,8- diazabicyclo[5.4.0]undec-7-ene (DBU) or 1 ,5-diazabicyclo[4.3.0]non-5-ene (DBN).

Preferred bases include carbonates and hydrides.

Particularly preferred bases include potassium carbonate, cesium carbonate and sodium hy- dride.

The term base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base. The molar ratio of the compound of formula (XXI) to the base is generally in the range of 1 :0.8- 3, preferably in the range of 1 :1 -2, more preferably in the range of 1 :1 -1 .5.

Preferably, the reaction of the compound of formula (XXI) with the compound of formula (XXII) in the presence of a base is carried out in a solvent.

Examples of suitable solvents are dipolar aprotic solvents such as N,N-dimethylformamide (DMF), Ν,Ν-dimethylacetamide (DMAc), 1 -methyl-2-pyrrolidinone (NMP), 1 ,3-dimethyl-2- imidazolidinone (DMI), Ν,Ν'-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO), sul- folane, acetonitrile, benzonitrile, acetone, methyl ethyl ketone, methyl butyl ketone, methyl iso- butyl ketone, cyclohexanone, nitromethane, nitroethane, nitrobenzene; esters such as ethyl acetate, butyl acetate, isobutyl acetate; ethers such as diethylether, dibutylether, tert-butyl methyl ether (TBME), 1 ,2-dimethoxyethane, tetrahydrofurane (THF), cyclopentyl methyl ether, 1 ,4- dioxane; alcohols such as methanol, ethanol, isopropanol, 1 -butanol, 2-butanol, isobutanol, tert- butanol, hexafluoro isopropanol; halogenated hydrocarbons such as dichloromethane, dichloro- ethane, carbon tetrachloride; aliphatic hydrocarbons such as hexane, cyclohexane; aromatic hydrocarbons such as benzene, toluene, xylenes, mesitylene, chlorobenzene. Preferred solvents include acetone, DMF, DMAc, 1 ,2-dimethoxyethane, DMI, dichloromethane, diethylether and THF.

Particularly preferred solvents include acetone, diethylether and THF. The term solvent as used herein also includes mixtures of two or more of the above compounds.

The reaction of the compound of formula (XXI) with the compound of formula (XXII) in the presence of a base is generally carried out at a temperature in the range of from -40 to 80 °C, pref- erably in the range of from -20 to 40 °C, more preferably in the range of from 0 to 30 °C.

Pests

Preferred animal pests are invertebrate pests.

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

The compounds of the formula I, and their salts are in particular suitable for efficiently controlling arthropodal pests such as arachnids, myriapedes and insects as well as nematodes.

The compounds of the formula I are especially suitable for efficiently combating the following pests: insects from the order of the lepidopterans (Lepidoptera), for example Acronicta major, Adox- ophyes orana, Aedia leucomelas, Agrotis spp. such as Agrotis fucosa, Agrotis segetum, Agrotis ypsilon; Alabama argillacea, Anticarsia gemmatalis, Anticarsia spp., Argyresthia conjugella, Au- tographa gamma, Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia murinana, Cacoecia podana, Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp. such as Chilo suppressalis; Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Clysia ambiguella, 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, Grapholitha fune- brana, Grapholitha molesta, Helicoverpa spp. such as Helicoverpa armigera, Helicoverpa zea; Heliothis spp. such as Heliothis armigera, Heliothis virescens, Heliothis 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 antennata, Lobesia botrana, Loxagrotis albicosta, Loxo- stege sticticalis, Lymantria spp. such as Lymantria dispar, Lymantria monacha; Lyonetia clerkel- la, Malacosoma neustria, Mamestra spp. such as Mamestra brassicae; Mods repanda, Mythim- na separata, Orgyia pseudotsugata, Oria spp., Ostrinia spp. such as Ostrinia nubilalis; Oulema oryzae, Panolis flammea, Pectinophora spp. such as Pectinophora gossypiella; Peridroma sau- cia, Phalera bucephala, Phthorimaea spp. such as Phthorimaea operculella; Phyllocnistis citrel- la, Pieris spp. such as Pieris brassicae, Pieris rapae; Plathypena scabra, Plutella maculipennis, Plutella xylostella, Prodenia spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera spp. such as Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura; Thaumatopoea pityocampa, Thermesia gemmatalis, 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, Agriotes obscurus; Amphimallus solstitialis, Anisandrus dispar, Anobium punctatum, Anomala rufocuprea, Ano- plophora spp. such as Anoplophora glabripennis; Anthonomus spp. such as Anthonomus gran- dis, Anthonomus pomorum; Anthrenus spp., Aphthona 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 Ceuthorrhynchus assimilis, Ceuthorrhynchus napi; Chaetocnema tibialis, Cleonus mendicus, Conoderus spp. such as Conoderus vespertinus; Cosmopolites spp., Costelytra zealandica, Crioceris asparagi, Cryptorhynchus lapathi, Ctenicera ssp. such as Ctenicera destructor; Cur- culio spp., Dectes texanus, Dermestes spp., Diabrotica spp. such as Diabrotica 12-punctata Diabrotica speciosa, Diabrotica longicornis, Diabrotica semipunctata, Diabrotica virgifera; Epi- lachna spp. such as Epilachna varivestis, Epilachna vigintioctomaculata; Epitrix spp. such as Epitrix hirtipennis; Eutinobothrus brasiliensis, Faustinus cubae, Gibbium psylloides, Heter- onychus arator, Hylamorpha elegans, Hylobius abietis, Hylotrupes bajulus, Hypera brunneipen- nis, Hypera postica, Hypothenemus spp., Ips typographus, Lachnostema consanguinea, Lema bilineata, Lema melanopus, 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; Melolon- tha hippocastani, Melolontha melolontha, Migdolus spp., Monochamus spp. such as Monocha- mus alternatus; Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzae- philus surinamensis, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllobius pyri, Phyllopertha hordeola, 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 sub- signatus; Symphyletes spp., Tenebrio molitor, Tribolium spp. such as Tribolium castaneum; Trogoderma spp., Tychius spp., Xylotrechus spp., and Zabrus spp. such as Zabrus tenebri- oides, 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 leucosphyrus, Anopheles maculi- pennis, 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 discalis, 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 coarc- tata, 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; Hy- poderma spp. such as Hypoderma lineata; Hyppobosca spp., Leptoconops torrens, Liriomyza spp. such as Liriomyza sativae, Liriomyza trifolii; Lucilia spp. such as Lucilia caprina, Lucilia cuprina, Lucilia sericata; Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. such as Mayetio- la 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, Psoro- phora 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, Tabanus lineola, Tabanus similis; Tannia spp., Tip- ula 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; Taeniothrips 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, Odontotermes spp., Reti- culitermes spp. such as Reticulitermes speratus, Reticulitermes flavipes, Reticulitermes grassei, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes virginicus; Termes natalen- sis, 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 brunnea, Periplaneta fuligginosa, Periplaneta japonica, bugs, aphids, leafhoppers, whiteflies, scale insects, cicadas {Hemiptera), e.g. Acrosternum spp. such as Acrosternum hilare; Acyrthosipon spp. such as Acyrthosiphon onobrychis, Acyrthosi- phon pisum; Adelges laricis, Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anasa tristis, Antestiopsis spp., Anuraphis car- dui, Aonidiella spp., Aphanostigma piri, Aphidula nasturtii, Aphis spp. such as Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis grossulariae, Aphis pomi, Aphis sambuci, Aphis schneideri, Aphis spiraecola; Arboridia apicalis, 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, Brachy- caudus persicae, Brachycaudus prunicola, Brachycolus spp., Brevicoryne brassicae, Calligypo- na marginata, Calocoris spp., Campylomma livid a, 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 hemipterus, Cimex lectula- rius; Coccomytilus halli, Coccus spp., Creontiades dilutus, Cryptomyzus ribis, Cryptomyzus ri- bis, Cyrtopeltis notatus, Da I bu I us 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; Dysaulacorthum pseudosolani, Dysdercus spp. such as Dysdercus cingula- tus, Dysdercus intermedius; Dysmicoccus spp., Empoasca spp. such as Empoasca fabae, Em- poasca solana; Eriosoma spp., Erythroneura spp., Eurygaster spp. such as Eurygaster integri- ceps; Euscelis bilobatus, Euschistus spp. such as Euschistuos heros, Euschistus impictiventris, Euschistus servus; Geococcus coffeae, Halyomorpha spp. such as Halyomorpha halys; He- liopeltis spp., Homalodisca coagulata, Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lac- tucae, lcerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepi- dosaphes spp., Leptocorisa spp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp. such as Lygus hesperus, Lygus lineolaris, Lygus pratensis; Macropes excavatus, Macrosiphum spp. such as Macrosiphum rosae, Macrosiphum avenae, Macrosiphum euphorbiae; Mahanarva fim- briolata, Megacopta cribraria, Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari, Met- cafiella 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 nigropictus, 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 bursarius; Pentomidae, Peregrinus ma id is, Perkinsiella saccharicida, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humu- //^', Phylloxera spp., Piesma quadrata, Piezodorus spp. such as Piezodorus guildinii, Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Psallus seriatus, Pseudacysta per- sea, Pseudaulacaspis pentagona, Pseudococcus spp. such as Pseudococcus comstocki; Psylla spp. such as Psylla mail, Psylla piri; Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Que- sada gigas, Rastrococcus spp., Reduvius senilis, Rhodnius spp., Rhopalomyzus ascalonicus, Rhopalosiphum spp. such as Rhopalosiphum pseudobrassicas, Rhopalosiphum insertum, Rhopalosiphum ma id is, Rhopalosiphum padi; Sagatodes spp., Sahlbergella singularis, Saissetia spp., Sappaphis mala, Sappaphis mail, Scaphoides titan us, Schizaphis graminum, Schizoneura lanuginosa, Scotinophora spp., Selenaspidus articulatus, Sitobion a venae, Sogata spp., Sogatella furcifera, Solubea insularis, Stephanitis nashi, Stictocephala festina, Tenalaphara malayensis, Thyanta spp. such as Thyanta perditor; Tibraca spp., Tinocallis caryaefoliae, To- maspis spp., Toxoptera spp. such as Toxoptera aurantii; Trialeurodes spp. such as Trialeurodes vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. such as Unaspis ya- nonensis; 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., Campo- notus 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, Monomorium pharaonis, Paravespula germanica, Paravespula pennsylvanica, Paravespula vulgaris, Pheidole megacephala, Pogonomyrmex barbatus, Pogonomyrmex californicus, 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 italicus, Chor- toicetes terminifera, Dociostaurus maroccanus, Gryllotalpa africana, Gryllotalpa gryllotalpa, Hie- roglyphus daganensis, Kraussaria angulifera, Locusta migratoria, Locustana pardalina, Mela- noplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Oedaleus senegalensis, Schistocerca ameri- cana, Schistocerca gregaria, Tachycines asynamorus, and Zonozerus variegatus, arachnids (Arachnida), such as acari,e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma spp. (e.g. Amblyomma americanum, Amblyomma variegatum, Amblyom- ma 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. Hyalomma truncatum), Ixodes spp. (e.g. Ixodes ricinus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus), Ornithodo- rus spp. (e.g. Ornithodorus moubata, Ornithodorus hermsi, Ornithodorus turicata), Ornithonys- sus 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 scabies), and Eriophyidae spp. such as Acaria sheldoni, Aculops spp. (e.g. Aculops pelekassi) Aculus spp. (e.g. Aculus schlechten- dali), Epitrimerus pyri, Phyllocoptruta oleivora and Eriophyes spp. (e.g. Eriophyes sheldoni); Tarsonemidae spp. such as Hemitarsonemus spp., Phytonemus pallidus and Polyphagotar- sonemus latus, Stenotarsonemus spp.; Tenuipalpidae spp. such as Brevipalpus spp. (e.g. Brevipalpus phoenicis); Tetranychidae spp. such as Eotetranychus spp., Eutetranychus spp., Oligonychus spp., Tetranychus cinnabarinus, 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 coleoptrata; 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, Pe- diculus humanus corporis; Pthirus pubis, Haematopinus spp. such as Haematopinus euryster- nus, 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 javanica, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species such as Aphelenchoides besseyi ; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus lignicolus Mamiya et Kiyohara, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocricone- ma species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Heliocotylen- chus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemi- cycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Lesion nematodes, Pratylenchus brachy- urus, 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 reniformis and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primi- tivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhyn- chus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species such as Tylenchulus semipenetrans; 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, Ancy- lostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., As- caris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp. such as Haemonchus contortus; Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercora lis, Stronyloides 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 Symphyla, 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 indi- cus, Chilo polychrysus, Chortiocetes terminifera, Cnaphalocroci medinalis, Cnaphalocrosis spp., Colias eurytheme, Collops spp., Cornitermes cumulans, Creontiades spp., Cyclocephala spp., Dalbulus maidis, Deraceras reticulatum, Diatrea saccharalis, Dichelops furcatus, Dicladispa armigera, Diloboderus spp. such as Diloboderus abderus; Edessa spp., Epinotia spp., Formici- dae, Geocoris spp., Globitermes sulfureus, Gryllotalpidae, Halotydeus destructor, Hipnodes bicolor, Hydrellia philippina, Julus spp., Laodelphax spp., Leptocorsia acuta, Leptocorsia orato- rius, Liogenys fuscus, Lucillia spp., Lyogenys fuscus, Mahanarva spp., Maladera matrida, Ma- rasmia spp., Mastotermes spp., Mealybugs, Megascelis ssp, Metamasius hemipterus, Microthe- ca spp., Mods latipes, Murgantia spp., Mythemina separata, Neocapritermes opacus, Neo- capritermes parvus, Neomegalotomus spp., Neotermes spp., Nymphula depunctalis, Oebalus pugnax, Orseolia spp. such as Orseolia oryzae; Oxycaraenus hyalinipennis, Plusia spp., Pomacea canaliculata, Procornitermes ssp, Procornitermes triacifer, Psylloides spp., Rachiplu- sia spp., Rhodopholus spp., Scaptocons castanea, Scaptocons spp., Scirpophaga spp. such as Scirpophaga incertulas, Scirpophaga innotata; Scotinophara spp. such as Scotinophara coarc- tata; Sesamia spp. such as Sesamia inferens, Sogaella frucifera, Solenapsis geminata, Spis- sistilus spp., Stalk borer, Stenchaetothrips biformis, Steneotarsonemus spinki, Sylepta deroga- ta, Telehin licus, Trichostrongylus spp..

Compounds of the formula I are particularly useful for controlling insects, preferably sucking or piercing insects such as insects from the genera Thysanoptera, Diptera and Hemiptera, in particular the following species:

Thysanoptera: Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips pa Imi and Thrips tabaci,

Diptera, e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles free- borni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pi pi ens, Culex nig ri palpus, Cu- lex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Lepto- conops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia seri- cata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocy- ami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psoro- phora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga spp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, Tipula oleracea, and Tipula paludosa;

Hemiptera, in particular aphids: Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Brachycaudus car- dui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lac- tucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella sacchancida, Phorodon humuli, Psylla mail, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sap- paphis mail, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes va- porariorum, Toxoptera aurantiiand, and Viteus vitifolii.

Hemiptera, in particular Nezara spp. such as Nezara viridula. Compounds of the formula I are particularly useful for controlling insects of the orders Hemiptera and Thysanoptera.

Compounds of the formula I are particularly useful for controlling Hemiptera, in particular Nezara spp. such as Nezara viridula.

Formulations

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 pests 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 animal pests species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound I used.

The compounds I and their salts can be converted into customary types of agrochemical com- positions, e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Mono-graph No. 2, 6th Ed. May 2008, CropLife International. The compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005. Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene, paraffin, tetrahydronaphtha- lene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclo- hexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N- methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; 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 am- photeric 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 alkylarylsul- fonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sul- fonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted 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-substititued 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 al- kylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinylpyrroli- done, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or pol- yethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones. Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.

Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, pol- yacrylates, 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.

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.

Emulsions (EW, EO, ES)

5-40 wt% of a compound I according to the invention and 1 -10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water- insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.

Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt% of a compound I according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1 -2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g. poly- vinylalcohol) is added.

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.

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.

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.

Microemulsion (ME)

5-20 wt% of a compound I according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alkohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.

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 isocy- anate monomer (e.g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solu-tion of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexa-methylenediamine) results in the formation of a polyurea microcapsules. The monomers amount to 1 -10 wt%. The wt% relate to the total CS composition.

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%.

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.

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% (ac- cording to NMR spectrum).

Solutions for seed treatment (LS), Suspo-emulsions (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 dress- ing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, compound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e.g. by seed dressing, pelleting, coating and dusting. When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.

In treatment of plant propagation materials such as seeds, e.g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.

When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.

Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.

The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.

In a further embodiment, either individual components of the composition according to the in- vention or partially premixed components, e.g. components comprising compounds I, may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.

In a further embodiment, either individual components of the composition according to the in- vention or partially premixed components, e.g. components comprising compounds I, can be applied jointly (e.g. after tank mix) or consecutively.

Mixtures According to one embodiment of the present invention, 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.1 to M.UN.X or F.I to F.XII, 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 and numbered according the Mode of Action Classification of the Insecticide Resistance Action Committee (IRAC), together with which the compounds 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, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodi- carb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or from the class of

M.1 B organophosphates, for example acephate, azamethiphos, azinphos-ethyl, azinphosme- thyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimetho- ate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O- (methoxyaminothio- phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion- methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupi- rimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothi- on; M.2. GABA-gated chloride channel antagonists such as:

M.2A cyclodiene organochlorine compounds, as for example endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), as for example ethiprole, fipronil, flufiprole, pyrafluprole and pyriprole; M.3 Sodium channel modulators from the class of

M.3A pyrethroids, for example acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifen- thrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta- cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha- cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, del- tamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, 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, niten- pyram, 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. tenebrionis, or the Bt crop proteins: CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1 ; M.12 Inhibitors of mitochondrial ATP synthase, for example

M.12A diafenthiuron, or

M.12B organotin miticides such as azocyclotin, cyhexatin or fenbutatin oxide, or M.12C pro- pargite, or M.12D tetradifon;

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

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

M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas as for example bistriflu- ron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novalu- ron, noviflumuron, teflubenzuron or triflumuron; M.16 Inhibitors of the chitin biosynthesis type 1 , as for example buprofezin;

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

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

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

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

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

M.21 Mitochondrial complex I electron transport inhibitors, for example

M.21A METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, or M.21 B rotenone;

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

M.22A indoxacarb, or M.22B metaflumizone, 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-N 1 -{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 com- pound

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.UN.X insecticidal active compounds of unknown or uncertain mode of action, as for example afidopyropen, azadirachtin, amidoflumet, benzoximate, bifenazate, bromopropylate, chinome- thionat, cryolite, dicofol, flufenerim, flometoquin, fluensulfone, flupyradifurone, piperonyl butox- ide, 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)-1 H- 1 ,2,4-triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 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.6†) (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 WO2006/013896. The aminofuranone com- pounds flupyradifurone is known from WO 2007/1 15644. The sulfoximine compound sulfoxaflor is known from WO2007/149134. The pyrethroid momfluorothrin is known from US6908945. The pyrazole acaricide pyflubumide is known from WO2007/020986. The isoxazoline compounds have been described likewise M.UN.X.1 in WO2005/085216, M.UN.X2. in WO2009/002809 and in WO201 1/149749 and the isoxazoline M.UN.X.9 in WO2013/050317. The pyripyropene derivative afidopyropen has been described in WO 2006/129714. The spiroketal-substituted cyclic ketoenol derivative M.UN.X.3 is known from WO2006/089633 and the biphenyl-substituted spi- rocyclic ketoenol derivative M.UN.X.4 from WO2008/06791 1. Finally triazoylphenylsulfide like M.UN.X.5 have been described in WO2006/043635 and biological control agents on basis of bacillus firmus in WO2009/124707. The neonicotionids 4A.1 is known from WO20120/069266 and WO201 1/06946, the M.4.A.2 from WO2013/003977, the M4.A.3.from WO2010/069266. 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 de- scribed in WO2005/077934. 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, WO2013/024009 and WO2013/024010, the anthranilamide Μ.28.5Ϊ) is described in WO201 1/085575, the M.28.5j) in WO2008/134969, the M.28.5k) in US201 1/046186 and the M.28.5I) in WO2012/034403. The diamide compounds M.28.6 and M.28.7 can be found in CN102613183. The compounds M.UN.X.6a) to M.UN.X.6i) listed in M.UN.X.6 have been described in WO2012/029672. The mesoionic antagonist compound M.UN.X.7 was described in WO2012/0921 15, the nematicide M.UN.X.8 in WO2013/055584 and the Pyridalyl-type analogue M.UN.X.10 in WO2010/060379. The following list of active fungicidal substances, in conjunction with which the compounds according to the invention can be used, is intended to illustrate the possible combinations but does not limit them:

F.I) Respiration Inhibitors

F.1-1 ) Inhibitors of complex III at Qo site (e.g. strobilurins)

strobilurins: azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metom- inostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyri- bencarb, trifloxystrobin, methyl (2-chloro-5 [1 -(3-methylbenzyloxyimino)ethyl]benzyl)carbamate and 2 (2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N methyl-acetamide;

oxazolidinediones and imidazolinones: famoxadone, fenamidone;

F.I-2) Inhibitors of complex II (e.g. carboxamides):

carboxanilides: benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, fluopyram, flutolanil, furametpyr, isopyrazam, isotianil, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-4 methyl-thiazole-5-carboxanilide, N- (3',4',5' trifluorobiphenyl-2 yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4 carboxamide, N-(4'- trifluoromethylthiobiphenyl-2-yl)-3 difluoromethyl-1-methyl-1 H pyrazole-4-carboxamide and N- (2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5 fluoro-1 H-pyrazole-4 carboxamide;

F.I-3) Inhibitors of complex III at Qi site: cyazofamid, amisulbrom;

F.I-4) Other respiration inhibitors (complex I, uncouplers)

diflumetorim; tecnazen; ferimzone; ametoctradin; silthiofam;

nitrophenyl derivates: binapacryl, dinobuton, dinocap, fluazinam, nitrthal-isopropyl,

organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide; F.ll) Sterol biosynthesis inhibitors (SBI fungicides)

F.II-1 ) C14 demethylase inhibitors (DMI fungicides, e.g. triazoles, imidazoles)

triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, dinicona- zole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hex- aconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, pen- conazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triad- imefon, triadimenol, triticonazole, uniconazole;

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

pyrimidines, pyridines and piperazines: fenarimol, nuarimol, pyrifenox, triforine;

F.II-2) Delta14-reductase inhitors (Amines, e.g. morpholines, piperidines)

morpholines: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph;

piperidines: fenpropidin, piperalin;

spiroketalamines: spiroxamine;

F.II-3) Inhibitors of 3-keto reductase: hydroxyanilides: fenhexamid;

F.lll) Nucleic acid synthesis inhibitors

F.III-1 ) RNA, DNA synthesis

phenylamides or acyl amino acid fungicides: benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, met- alaxyl-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, fuber- idazole, thiabendazole, thiophanate-methyl;

triazolopyrimidines: 5-chloro-7 (4-methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)- [1 ,2,4]triazolo[1 ,5 a]pyrimidine

F.IV-2) Other cell division inhibitors

benzamides and phenyl acetamides: diethofencarb, ethaboxam, pencycuron, fluopicolide, zox- amide;

F.IV-3) Actin inhibitors: benzophenones: metrafenone; F.V) Inhibitors of amino acid and protein synthesis

F.V-1 ) Mmethionine synthesis inhibitors (anilino-pyrimidines)

anilino-pyrimidines: cyprodinil, mepanipyrim, nitrapyrin, pyrimethanil;

F.V-2) Protein synthesis inhibitors (anilino-pyrimidines)

antibiotics: blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomycin, strep- tomycin, 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.VII) Lipid and membrane synthesis inhibitors

F.VII-1 ) Phospholipid biosynthesis inhibitors

organophosphorus compounds: edifenphos, iprobenfos, pyrazophos;

dithiolanes: isoprothiolane;

F.VII-2) Lipid peroxidation

aromatic hydrocarbons: dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole;

F.VII-3) Carboxyl acid amides (CAA fungicides)

cinnamic or mandelic acid amides: dimethomorph, flumorph, mandiproamid, pyrimorph;

valinamide carbamates: benthiavalicarb, iprovalicarb, pyribencarb, valifenalate and N-(1 -(1 -(4- cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;

F.VII-4) Compounds affecting cell membrane permeability and fatty acides

carbamates: propamocarb, propamocarb-hydrochlorid

F.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, flusulfamide, hex- achlorobenzene, pentachlorphenole and its salts, phthalide, tolylfluanid, N-(4-chloro-2-nitro- phenyl)-N-ethyl-4-methyl-benzenesulfonamide;

F.VIII-4) Guanidines: guanidine, dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate);

F.VIII-5) Ahtraquinones: dithianon;

F.IX) Cell wall synthesis inhibitors

F.IX-1 ) Inhibitors of glucan synthesis: validamycin, polyoxin B;

F.IX-2) Melanin synthesis inhibitors: pyroquilon, tricyclazole, carpropamide, dicyclomet, fenoxanil;

F.X) Plant defence inducers

F.X-1 ) Salicylic acid pathway: acibenzolar-S-methyl;

F.X-2) Others: probenazole, isotianil, tiadinil, prohexadione-calcium;

phosphonates: fosetyl, fosetyl-aluminum, phosphorous acid and its salts;

F.XI) Unknown mode of action: bronopol, chinomethionat, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, difen- zoquat, difenzoquat-methylsulfate, diphenylamin, flumetover, flusulfamide, flutianil, methasul- focarb, 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, 3-[5-(4- methyl-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine, 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) cyclopropane- carboxylic acid amide, 5-chloro-1 (4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole, 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide;

F.XI) Growth regulators:

abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6- dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N 6 benzyladenine, paclobutrazol, prohexadione (prohexadione- calcium), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5 tri iodo- benzoic acid, trinexapac-ethyl and uniconazole; F.XI I) Biological control agents

antifungal biocontrol agents: Bacillus substilis strain with NRRL No. B-21661 (e.g. RHAPSODY®, SERENADE® MAX and SERENADE® ASO from AgraQuest, Inc., USA.), Bacillus pu- milus strain with NRRL No. B-30087 (e.g. SONATA® and BALLAD® Plus from AgraQuest, Inc., USA), Ulocladium oudemansii (e.g. the product BOTRY-ZEN from BotriZen Ltd., New Zealand), Chitosan (e.g. ARMOUR-ZEN from BotriZen Ltd., New Zealand).

Applications

The animal pest, i.e. the insects, arachnids and nematodes, the plant, soil or water in which the plant is growing can be contacted with the present compounds of formula I or composition(s) containing them by any application method known in the art. As such, "contacting" includes both direct contact (applying the compounds/compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the com- pounds/compositions to the locus of the animal pest or plant).

The compounds of formula I 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 formula I. 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, sugar- beet, 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 a insecticidally effective amount of the active compounds. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the insects. The present invention also includes a method of combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, cultivated plants, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of a mixture of at least one active compound I.

Moreover, animal 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 formula I. 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 invention can also be applied preventively to places at which occurrence of the pests is expected.

The compounds of formula I may be also used to protect growing plants from attack or infesta- tion by pests by contacting the plant with a pesticidally effective amount of compounds of formula I. 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. 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. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be in- eluded. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.

The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering. 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-transtional modification of protein(s) (oligo- or polypeptides) poly for example by glycosylation or polymer additions such as prenyl- ated, acetylated or farnesylated moieties or PEG moieties (e.g. as disclosed in Biotechnol Prog. 2001 Jul-Aug;17(4):720-8., Protein Eng Des Sel. 2004 Jan;17(1 ):57-66, Nat Protoc.

2007;2(5):1225-35., Curr Opin Chem Biol. 2006 Oct;10(5):487-91. Epub 2006 Aug 28., Bio- materials. 2001 Mar;22(5):405-17, Bioconjug Chem. 2005 Jan-Feb;16(1 ):1 13-21 ).

The term "cultivated plants" is to be understood also including plants that have been rendered tolerant to applications of specific classes of herbicides, such as hydroxyphenylpyruvate dioxy- genase (HPPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e.g. US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imidazolinones (see e.g. US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073); enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate (see e.g. WO 92/00377); glutamine synthetase (GS) inhibitors, such as glufosinate (see e.g. EP-A-0242236, EP-A-242246) or oxynil herbicides (see e.g. US 5,559,024) as a result of conventional methods of breeding or genetic engineering. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), for example Clearfield® summer rape (Canola) being tolerant to imidazolinones, e.g. imazamox. 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) and LibertyLink® (glufosinate). The term "cultivated plants" is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as delta-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, for example 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 receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, for example WO 02/015701 ). Further examples of such toxins or genetically-modified plants capable of synthesizing such toxins are disclosed, for ex- ample, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO

03/018810 und WO 03/052073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins protection from harmful pests from certain taxo- nomic groups of arthropods, particularly to beetles (Coleoptera), flies (Diptera), and butterflies and moths (Lepidoptera) and to plant parasitic nematodes (Nematoda).

The term "cultivated plants" is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the re- sistance 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, for example EP-A 0 392 225), plant disease resistance genes (for example potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato So- lanum bulbocastanum) or T4-lysozym (e.g. potato cultivars capable of synthesizing these pro- teins 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, for example, in the publications mentioned above.

The term "cultivated plants" is to be understood also including plants that are by the use of re- combinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants. The term "cultivated plants" is to be understood also including plants 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, for example oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e.g. Nex- era® rape).

The term "cultivated plants" is to be understood also including plants 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, for example potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato).

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 25 g to 600 g per hectare, more desirably from 50 g to 500 g per hectare.

The compounds of formula I 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 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 formula I 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 compound.

Formulations of compounds of formula I 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 com- pound, 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 emulsifi- ers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.

The oil spray formulations differ from the aerosol recipes in that no propellants are used.

For use in spray compositions, the content of active ingredient is from 0.001 to 80 weight %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.

The compounds of formula I 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 formula I and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder. Suitable repellents for example are Ν,Ν-Diethyl-meta-toluamide (DEET), N,N- diethylphenylacetamide (DEPA), 1 -(3-cyclohexan-1 -yl-carbonyl)-2-methylpiperine, (2-hydroxy- methylcyclohexyl) acetic acid lactone, 2-ethyl-1 ,3-hexandiol, indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insect control such as {(+/-)-3-allyl-2-methyl-4-oxocyclopent- 2-(+)-enyl-(+)-trans-chrysantemate (Esbiothrin), a repellent derived from or identical with plant extracts like limonene, eugenol, (+)-Eucamalol (1 ), (-)-l -epi-eucamalol or crude plant extracts from plants like Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogan nartdus (citronella). Suitable binders are selected for example from polymers and copolymers of vinyl esters of aliphatic acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2- ethylhexylacrylate, and methyl acrylate, mono- and di-ethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadiene.

The impregnation of curtains and bednets is done in general by dipping the textile material into emulsions or dispersions of the insecticide or spraying them onto the nets.

The compounds of formula I and its 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 formula I 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.

Seed treatment

The compounds of formula I are also suitable for the treatment of seeds in order to protect the seed 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 formula I 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 seedling's 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 general formula I or a salt thereof. Particularly preferred is a method, wherein the plant's roots and shoots are protected, more preferably a method, wherein the plants shoots are protected form piercing and sucking insects, most preferably a method, wherein the plants shoots are protected from aphids. The term seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.

The term seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting.

The present invention also comprises seeds coated with or containing the active compound.

The term "coated with and/or containing" generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a great- er 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 ex- ample seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Bras- sica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.

In addition, the active compound may also be used for the treatment of seeds from plants, which tolerate the action of herbicides or fungicides or insecticides owing to breeding, including genetic engineering methods.

For example, the active compound can be employed in treatment of seeds from plants, which are resistant to herbicides from the group consisting of the sulfonylureas, imidazolinones, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active substances (see for example, EP-A-0242236, EP-A-242246) (WO 92/00377) (EP-A-0257993, U.S. Pat. No. 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- 0142924, EP-A-0193259),

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 formula I 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), op- tionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight. Seed treatment formulations may additionally also comprise binders and optionally colorants.

Binders can be added to improve the adhesion of the active materials on the seeds after treatment. Suitable binders are homo- and copolymers from alkylene oxides like ethylene oxide or propylene oxide, polyvinylacetate, polyvinylalcohols, polyvinylpyrrolidones, and copolymers thereof, ethylene-vinyl acetate copolymers, acrylic homo- and copolymers, polyethyleneamines, polyethyleneamides and polyethyleneimines, polysaccharides like celluloses, tylose and starch, polyolefin homo- and copolymers like olefin/maleic anhydride copolymers, polyurethanes, polyesters, polystyrene homo and copolymers Optionally, also colorants can be included in the formulation. Suitable colorants or dyes for seed treatment formulations are Rhodamin B, C.I. Pigment Red 1 12, C.I. Solvent Red 1 , pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.

An example of a gelling agent is carrageen (Satiagel^®). In the treatment of seed, the application rates of the compounds I are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed.

The invention therefore also relates to seed comprising a compound of the formula I, or an agri- culturally useful salt of I, as defined herein. The amount of the compound I or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher. Animal health

The compounds of formula I or veterinarily acceptable salts thereof are in particular also suitable for being used for combating parasites in and on animals. An object of the present invention is therefore also to provide new methods to control parasites in and on animals. Another object of the invention is to provide safer pesticides for animals. Another object of the invention is further to provide pesticides for animals that may be used in low- er 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 containing a parasiticidally effective amount of compounds of formula I or veterinarily acceptable salts thereof and an acceptable carrier, for combating parasites in and on animals.

The present invention also provides a method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises orally, topically or par- enterally administering or applying to the animals a parasiticidally effective amount of a compound of formula I or veterinarily acceptable salts thereof or a composition comprising it.

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 com- prises a parasiticidally effective amount of a compound of formula I or veterinarily acceptable salts thereof 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 dosag- es 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 are suitable for combating en- do- and ectoparasites in and on animals.

Compounds of formula I or veterinarily acceptable salts thereof and compositions comprising them are preferably used for controlling and preventing infestations and infections 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 formula I or veterinarily acceptable salts thereof and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals, such as dogs or cats.

Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas. The compounds of formula I or veterinarily acceptable salts thereof 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 formula I are especially useful for combating ectoparasites.

The compounds of formula I are especially useful for combating parasites of the following orders and species, respectively: fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides cams, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus, cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta aus- tralasiae, and Blatta orientalis, flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gam- biae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadri- maculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macel- laria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinque- fasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia ca- nicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrhoi- dalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atra- tus, Tabanus lineola, and Tabanus similis, lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus. ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocy- clus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssus galli- nae,

Actinedida (Prostigmata) und Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Orni- thocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Pso- roptes 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 Sole- nopotes spp,

Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Feli- cola spp, Roundworms Nematoda:

Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae,) Trichuris spp., Capillaria spp, Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp,

Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stepha- nurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Al- eurostrongylus abstrusus, and Dioctophyma renale,

Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi,

Camallanida, e.g. Dracunculus medinensis (guinea worm) Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.,

Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp,

Planarians (Plathelminthes): Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria a lata, 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 compounds of formula I and compositions containing them are particularly useful for the control of pests from the orders Diptera, Siphonaptera and Ixodida.

Moreover, the use of the compounds of formula I and compositions containing them for combating mosquitoes is especially preferred.

The use of the compounds of formula I and compositions containing them for combating flies is a further preferred embodiment of the present invention.

Furthermore, the use of the compounds of formula I and compositions containing them for com- bating fleas is especially preferred.

The use of the compounds of formula I and compositions containing them for combating ticks is a further preferred embodiment of the present invention. The compounds of formula I also are especially useful for combating endoparasites (roundworms nematoda, thorny headed worms and planarians).

Administration can be carried out both prophylactically and therapeutically.

Administration of the active compounds is carried out directly or in the form of suitable prepara- tions, orally, topically/dermally or parenterally.

For oral administration to warm-blooded animals, the formula I compounds may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the formula I compounds may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day. Alternatively, the formula I compounds may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The formula I compounds may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the formula I compounds may be formulated into an implant for subcuta- neous administration. In addition the formula I compound may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound. The formula I compounds may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the formula I compound. In addition, the formula I compounds may be formulated as ear tags for animals, particularly quad- rupeds such as cattle and sheep.

Suitable preparations are:

- Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;

- Emulsions and suspensions for oral or dermal administration; semi-solid preparations;

- Formulations in which the active compound is processed in an ointment base or in an oil-in- water or water-in-oil emulsion base;

- Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.

Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further ingredients such as acids, bases, buffer salts, preservatives, and solubilizers. The solutions are filtered and filled sterile. Suitable solvents are physiologically tolerable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methyl-pyrrolidone, 2-pyrrolidone, and mixtures thereof.

The active compounds can optionally be dissolved in physiologically tolerable vegetable or syn- thetic oils which are suitable for injection.

Suitable solubilizers are solvents which promote the dissolution of the active compound in the main solvent or prevent its precipitation. Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester.

Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n- butanol.

Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.

Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on. Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary. In general, "parasiticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions used in the invention. A parasiticidally effective amount of the composi- tions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.

The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compound of formula I. Generally it is favorable to apply the compounds of formula I in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.

Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 per cent by weight, preferably from 0.1 to 65 per cent by weight, more preferably from 1 to 50 per cent by weight, most preferably from 5 to 40 per cent by weight.

Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 per cent by weight, preferably of 1 to 50 per cent by weight.

Furthermore, the preparations comprise the compounds of formula I against endoparasites in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 per cent by weight, very particularly preferably of 0.005 to 0.25 per cent by weight. In a preferred embodiment of the present invention, the compositions comprising the compounds of formula I them are applied dermally / topically.

In a further preferred embodiment, the topical application is conducted in the form of compound- containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.

Generally it is favorable to apply solid formulations which release compounds of formula I in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.

For the preparation of the shaped articles, thermoplastic and flexible plastics as well as elastomers and thermoplastic elastomers are used. Suitable plastics and elastomers are polyvinyl resins, polyurethane, polyacrylate, epoxy resins, cellulose, cellulose derivatives, polyamides and polyester which are sufficiently compatible with the compounds of formula I. A detailed list of plastics and elastomers as well as preparation procedures for the shaped articles is given e.g. in WO 03/086075. The invention is illustrated by the following examples without being limited thereby.

Examples

A. Preparation examples

With appropriate modification of the starting materials, the procedure given in the synthesis example below was used to obtain further compounds II. The compounds obtained in this manner are listed in the table that follows, together with physical data. The products shown below were characterized by NMR spectroscopy or by the masses ([m/z]) or retention times (RT; [min.]) determined by HPLC-MS or HPLC spectrometry.

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

Method 1 : RP-18 column (Chromolith® Speed ROD from Merck KGaA, Germany), 50^*4.6 mm; mobile phase: acetonitrile + 0.1 % trifluoroacetic acid (TFA)/water + 0.1 % TFA, using a gradient of 5:95 to 100:0 over 5 minutes at 40°C, flow rate 1.8 ml/min.

Method 2: Phenomenex Kinetex 1 .7 μηη 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.Oml/min in 1.50 minutes at 60°C.

MS: quadrupole electrospray ionization (positive mode).

Procedure for the preparation of 2-[(5-chloro-3-thienyl)methyl]-2-(3,4,5- trifluorophenyl)propanedinitrile (II-34):

2-(3,4,5-trifluorophenyl)propanedinitrile (150 mg, 0.76 mmol, 1 .0 equiv.) was dissolved in ace- tone (4 ml_), K2CO3 (190 mg, 1.38 mmol, 1 .8 equiv.) was added and the reaction mixture was stirred at room temperature for 20 min. A solution of 4-(bromomethyl)-2-chloro-thiophene (279 mg, 1 .15 mmol, 1 .5 equiv.) in acetone (3 ml.) was added dropwise and the resulting mixture was stirred at room temperature overnight. The reaction was then quenched by addition of water and extracted with ethyl acetate (3 x). The combined organic layers were washed with H2O (2x) and with brine (1 *), dried over Na2S0₄, filtered and the solvent was removed under reduced pressure to yield the crude product. Subsequent purification via column chromatography (S1O2, cyclohexane/ethyl acetate gradient 50/1→ 8/1 ) then yielded 183 mg (0.56 mmol, 74%) of II-34. Procedure for the preparation of 2-(3,5-difluorophenyl)-2-[(2-methylthiazol-4- yl)methyl]propanedinitrile (II-42):

2-(3,5-difluorophenyl)propanedinitrile (150 mg, 0.84 mmol, 1 .0 equiv.) was dissolved in acetone (3 ml_), K2CO3 (175 mg, 1.26 mmol, 1 .5 equiv.) was added and the reaction mixture was stirred at room temperature for 20 min. A catalytic amount of sodium iodide was added, subsequently a solution of 4-(chloromethyl)-2-methyl-thiazole (141 mg, 0.93 mmol, 1 .1 equiv.) in acetone (2 mL) was added dropwise, and the resulting mixture was stirred at room temperature overnight. The reaction was then quenched by addition of water and extracted with ethyl acetate (3 x). The combined organic layers were washed with H2O (2*) and with brine (1 *), dried over Na2S0₄, filtered and the solvent was removed under reduced pressure to yield the crude product. Subsequent purification via column chromatography (S1O2, cyclohexane/ethyl acetate 4/1 ) then yielded 20 mg (0.07 mmol, 9%) of II-42.

physical data (LC-MS)

Comp. R51 R52 R53 R54 R55 Q

m/z

RT [min]

[MH]+

11-1 H H H H H H 5-tert-bu tyl- 1 , 3,4-oxad iazol-2-yl

II-2 H H H H H H 5-isopropyl- 1 ,2 ,4-oxad iazol-3-yl

II-3 H H CI H H H 5-cyclopropyl- 1 , 3,4-th iad iazol-2-yl 3.382^ 315.0

II-4 H H CI H H H 5-methyl-1 ,3,4-oxadiazol-2-yl 2.959^a 273.1

II-5 H H CI H H H 5-isopropyl- 1 , 3,4-oxad iazol-2-yl 3.377^a 301 .1

II-6 H H CI H H H 2-chlorothiazol-5-yl 3.71 1^ 308.0

II-7 H H CI H H H 5-isopropyl- 1 ,2 ,4-oxad iazol-3-yl

II-8 H H H H H H 5-(trifluoromethyl)-thiophen-2-yl

II-9 H H F H H H 5-(trifluoromethyl)-thiophen-2-yl

11-10 H H F H H H 5-(trifluoromethyl)-furan-2-yl

11-1 1 H H H H H H 5-(trifluoromethyl)-furan-2-yl

11-12 H H F H H H 5-ethynyl-th iophen-2-yl 1.225^b 281 .0

11-13 H H H H H H 5-ethynyl-th iophen-2-yl 1.225^b 263.1

5-(trifluoromethyl)-1 , 3,4-

11-14 H H H H H H 3.450^a 293.1 oxad iazol-2-yl

5-(trifluoromethyl)-1 , 3,4-

11-15 H H F H H H 3.508^a 31 1.0 oxad iazol-2-yl

11-16 H H H H H H 5-methylisoxazol-3-yl

11-17 H H F H H H 5-methylisoxazol-3-yl

11-18 H F H F H H 5-methylisoxazol-3-yl

11-19 H F F F H H thiophen-3-yl

II-20 H F F F H H furan-3-yl 11-21 H F F F H H 1 ,5-dimethylpyrazol-3-yl

II-22 H F F F H H 2-methylthiazol-4-yl

II-23 H F F F H H imidazo[1 ,2-a]pyridin-2-yl

II-24 H F F F H H 5-isopropyl- 1 ,2 ,4-oxad iazol-3-yl

II-25 H F F F H H 5-ethyl-1 ,2,4-oxadiazol-3-yl

II-26 H F F F H H 1 ,3-dimethylpyrazol-5-yl

II-27 H F F F H H 3,5-dimethylisoxazol-4-yl

II-28 H F F F H H thiazol-4-yl

II-29 H F F F H H 5-methyl-1 ,2,4-oxadiazol-3-yl

II-30 H F F F H H 1 ,2,4-triazol-1-yl

1-methyl-3-

11-31 H F F F H H

(trifluoromethyl)pyrazol-5-yl

II-32 H F F F H H 5-chlorobenzothiophen-3-yl

II-33 H F F F H H 5-methyl-isoxazol-3-yl

II-34 H F F F H H 2-chlorothiophen-4-yl

II-35 H F F F H H 2,3-dibromothiophen-4-yl

II-36 H F H F H H 1 ,5-dimethylpyrazol-3-yl

II-37 H F H F H H imidazo[1 ,2-a]pyridin-2-yl

II-38 H F H F H H 5-ethyl-1 ,2,4-oxadiazol-3-yl

II-39 H F H F H H 1 ,3-dimethylpyrazol-5-yl

II-40 H F H F H H 3,5-dimethylisoxazol-4-yl

11-41 H F H F H H 5-chlorobenzothiophen-3-yl

II-42 H F H F H H 2-methylthiazol-4-yl

II-43 H F H F H H 5-isopropyl- 1 ,2 ,4-oxad iazol-3-yl

II-44 H F H F H H thiazol-4-yl

II-45 H F H F H H 5-methyl-1 ,2,4-oxadiazol-3-yl

1-methyl-3-

II-46 H F H F H H

(trifluoromethyl)pyrazol-5-yl

II-47 H F H F H H 1 ,2,4-triazol-1-yl

II-48 H H F H H H 5-cyclopropyl- 1 , 3,4-oxad iazol-2-yl 1 ,023^b 282,8

II-49 H H F H H H 5-ethyl-1 ,3,4-oxadiazol-2-yl 0.996^b 270.8

II-50 H H F H H H 5-tert-bu tyl- 1 , 3,4-oxad iazol-2-yl 1.1 14^b 298.8

11-51 H F F F H H 5-tert-bu tyl- 1 , 3,4-oxad iazol-2-yl 1.025^b 335.4

II-52 H H F H H H 3-methyl-1 ,2,4-oxadiazol-5-yl

II-53 H F F F H H 3-methyl-1 ,2,4-oxadiazol-5-yl

II-54 H H F H H H 2-methyloxazol-5-yl

II-55 H F F F H H 2-methyloxazol-5-yl

II-56 H H F H H H 5-methyloxazol-2-yl 1.045^b 256.0

II-57 H F F F H H 5-methyloxazol-2-yl 1.1 10" 291 .9 II-58 H F F F H H 3-methylisothiazol-5-yl 1.144^b 307.9

II-59 H H F H H H 2-tert-butyloxazol-5-yl 1.173^b 298.0

II-60 H F F F H H 2-tert-butyloxazol-5-yl 1.225^b 334.0

11-61 H H F H H H 3-methylisoxazol-5-yl 1.064^b 253.9

II-62 H F F F H H 3-methylisoxazol-5-yl 1.122^b 289.9

II-63 H H F H H H 3-(trifluoromethyl)isoxazol-5-yl 1.199^c 308.1

II-64 H F F F H H 3-tert-bu tyl- 1 ,2 ,4-oxad iazol-5-yl 1.294= 333.1

II-65 H H F H H H 3-tert-bu tyl- 1 ,2 ,4-oxad iazol-5-yl 1.238^c 296.9

II-66 H H F H H H 3-methylisothiazol-5-yl 1.106^c 269.9

II-67 H H F H H H 3-tert-butylisoxazol-5-yl 1.234= 295.9

II-68 H F F F H H 3-tert-butylisoxazol-5-yl 1.273^b 334.0

II-69 H H F H H H 2-(trifluoromethyl)thiazol-4-yl 1.233^c 323.8

II-70 H F F F H H 4-(trifluoromethyl)thiazol-2-yl 1.250^c 360.0

11-71 H F F F H H 2-(trifluoromethyl)thiazol-4-yl

II-72 H H F H H H 5-(trifluoromethyl)thiazol-2-yl 1.228^c 323.8

II-73 H F F F H H 2-chlorothiazol-5-yl 1.200^b 327.9

II-74 H F F F H H 5-(trifluoromethyl)thiazol-2-yl 1.279^c 360.1

II-75 H H F H H H 2-chlorothiazol-5-yl 1.146^b 292.0

II-76 H F F F H H 3-bromoisoxazol-5-yl 1.201 ^b 355.5

II-77 H H F H H H 4-(trifluoromethyl)thiazol-2-yl 1.208^c 323.8

II-78 H H F H H H 2-(trifluoromethyl)thiazol-5-yl 1.225^c 323.8

II-79 H F F F H H 2-(trifluoromethyl)thiazol-5-yl 1.269^c 359.8

II-80 H H F H H H 2-tert-butylthiazol-4-yl

11-81 H H F H H H 2-tert-butylthiazol-5-yl 1.226 314.0

II-82 H H F H H H 1 ,3,4-thiadiazol-2-yl

II-83 H H F H H H 5-tert-bu tyl- 1 ,2 ,4-oxad iazol-3-yl 1.245 296.8

II-84 H F F F H H 5-tert-bu tyl- 1 ,2 ,4-oxad iazol-3-yl 1.298 332.8

II-85 H H F H H H 2-tert-butyloxazol-4-yl 1.277^b 295.9

II-86 H F F F H H 2-tert-butyloxazol-4-yl 1.331 331 .8

II-87 H F F F H H 1 ,3,4-thiadiazol-2-yl 0.987^b 294.9

II-88 H H F H H H 5-methylthiazol-2-yl 1.124b 269.8

II-89 H F F F H H 5-methylthiazol-2-yl 1.188 305.8

II-90 H F F F H H 2-tert-butylthiazol-4-yl 1.366 349.9

11-91 H F F F H H 2-tert-butylthiazol-5-yl 1.302^b 350.1

II-92 H H F H H H 5-tert-butylthiazol-2-yl 1.276 314.1

II-93 H F F F H H 5-tert-butylthiazol-2-yl 1.327^b 350.0 ^a HPLC method 1 (see above)

b HPLC method 2 (see above)

c HPLC method 2 (see above), MS: quadrupole electrospray ionization (negative mode). NMRdata:

Comp. II-7: ¹H-NMR (400 MHz,CDCI₃): δ = 1.40(2 d, 3H each), 3.23(quint, 1H), 3.66(s, 2H), 7.48(d, 2H), 7.55(d, 2H) ppm.

Comp. II-8: H-NMR (500 MHz,CDCI₃): δ = 3.70(s, 2H), 6.95(d, 1H), 7.30(d, 1H), 7.50(s, 5H) ppm.

Comp. II-9: H-NMR (500 MHz,CDCI₃): δ = 3.70(s, 2H), 6.95(s, 1H), 7.20(m, 2H), 7.35(s,1H), 7.50(m, 2H) ppm.

Comp.11-10: H-NMR (500 MHz.CDCb_. : δ = 3.60(s, 2H), 6.45(d, 1H), 6.75(d, 1H), 7.10-7.20(m, 2H), 7.40-7.50(m, 2H) ppm.

Comp.11-11: H-NMR(500 MHz,CDCI₃ : δ = 3.60(s, 2H), 6.45(s,1H), 6.75(s, 1H), 7.50(s, 5H) ppm.

Comp.11-14: H-NMR (500 MHz,CDCI₃ : δ 3.95(s, 2Η), 7.50-7.60(m, 5Η) ppm.

Comp.11-15: H-NMR (500 MHz,CDCI₃ : δ 3.95(s, 2H), 7.20-7.30(m, 2H), 7.55-7.65(m, 2H) ppm.

Comp.11-16: H-NMR (400 MHz,CDCI₃ : δ 2.45(s, 3H), 3.55(s, 2H), 6.10(s, 1H), 7.50(m, 3H), 7.60(m, 2H) ppm.

Comp.11-17: ¹H-NMR (400 MHz,CDCI₃ : δ 2.45(s, 3H), 3.55(s, 2H), 6.10(s, 1H), 7.20(t, 2H), 7.50-7.60(m, 2H) ppm.

Comp.11-18: H-NMR (400 MHz,CDCI₃ : δ 2.45(s, 3H), 3.55(s, 2H), 6.10(s, 1H), 6.95(t, 1H), 7.15(d, 2H) ppm.

Comp.11-19: H-NMR (400 MHz,CDCI₃ : δ 3.55(s, 2H), 6.85(d, 1H), 7.05-7.15(m, 2H), 7.20(m, 1H), 7.35(m, 1H) ppm.

Comp. II-20: H-NMR (400 MHz,CDCI₃ : δ 3.35(s, 2H), 6.30(s, 1H), 7.15-7.25(m, 2H), 7.40(d, 1H),7.45(d, 1H)ppm.

Comp.11-21 : ¹H-NMR (400 MHz,CDCI₃ : δ 2.25(s, 3H), 3.50(s, 2H), 3.60(s, 3H), 6.05(s, 1H), 7.20(t, 2H) ppm

Comp. II-22: ¹H-NMR (500 MHz,CDCI₃ : δ 2.70(s, 3H), 3.60(s, 2H), 7.15(s, 1H), 7.20(q, 2H) ppm.

Comp. II-23: H-NMR (400 MHz,CDCI₃ : δ 3.75(s, 2H), 6.85(t, 1H), 7.25-7.30(m, 3H), 7.60(dd,

1H), 7.70(s, 1H), 8.15(dd, 1H) ppm.

Comp. II-24: ¹H-NMR (400 MHz,CDCI₃ : δ 1.35-1.45(m, 6H), 3.20-3.30(m, 1H), 3.65(s, 2H),

7.20-7.30(m, 2H) ppm.

Comp. II-25: H-NMR (500 MHz,CDCI₃ : δ 1.40(t, 3H), 2.95(t, 2H), 3.70(s, 2H), 7.30(t, 2H) ppm.

Comp. II-26: H-NMR (400 MHz,CDCI₃ : δ 2.25(s, 3H), 3.50(s, 2H), 3.60(s, 3H), 6.05(s, 1H),

7.15(q, 2H) ppm.

Comp. II-27: ¹H-NMR (400 MHz,CDCI₃ : δ 2.05(s, 3H), 2.30(s, 3H), 3.30(s, 2H), 7.20(q, 2H) ppm.

Comp. II-28: H-NMR (500 MHz,CDCI₃ : δ 3.75(s, 2H), 7.20(t, 2H), 7.40(s, 1H), 8.80(s, 1H) ppm.

Comp. II-29: H-NMR (500 MHz,CDCI₃ : δ 2.65(s, 3H), 3.65(s, 2H), 7.30(t, 2H) ppm. Comp. II-30: ¹H-NMR (500 MHz,CDCI₃): δ = 4.90(s, 2H), 7.20(t, 2H), 8.00(s, 1 H), 8.20(s, 1 H) ppm.

Comp. 11-31 : H-NMR (400 MHz,CDCI₃): δ = 3.60(s, 2H), 3.85(s, 3H), 6.55(s, 1 H), 7.20(q, 2H) ppm.

Comp. II-32: ¹H-NMR (400 MHz,CDCI₃): δ = 3.75(s, 2H), 7.15(q, 2H), 7.20(d, 1 H), 7.35(dd, 1 H), 7.60(s, 1 H), 7.80(d, 1 H) ppm.

Comp. II-33: H-NMR (400 MHz,CDCI₃): δ = 2.45(s, 3H), 3.55(s, 2H), 6.15(s, 1 H), 7.20-7.30(m, 2H) ppm.

Comp. II-34: H-NMR (400 MHz,CDCI₃): δ = 3.40(s, 2H), 6.75(d, 1 H), 6.95(d, 1 H), 7.10-7.20(q, 2H) ppm.

Comp. II-35: H-NMR (500 MHz,CDCI₃): δ = 3.60(s, 2H), 7.15(t, 2H), 7.55(s, 1 H) ppm.

Comp. II-36: ¹H-NMR (400 MHz,CDCI₃): δ = 2.25(s, 3H), 3.50(s, 2H), 3.55(s, 3H), 6.05(s, 1 H), 6.95-7.00(m, 1 H), 7.00-7.10(m, 2H) ppm.

Comp. 11-37: ¹H-NMR (400 MHz,CDCI₃): δ = 3.75(s, 2H), 6.85-6.95(m, 2H), 7.15(dd, 2H), 7.20- 7.30(m, 1 H), 7.60(dd, 1 H), 7.70(s, 1 H), 8.15(dd, 1 H) ppm.

Comp. II-38: ¹H-NMR (500 MHz,CDCI₃): δ = 1.40(t, 3H), 2.95(t, 2H), 3.65(s, 2H), 6.95-7.00(m, 1 H), 7.20(d, 2H) ppm.

Comp. II-39: ¹H-NMR (500 MHz,CDCI₃): δ = 2.25(s, 3H), 3.50(s, 2H), 3.60(s, 3H), 6.05(s, 1 H), 6.95-7.00(m, H), 7.05(d, 2H) ppm.

Comp. II-40: H-NMR (500 MHz,CDCI₃): δ = 2.05(s, 3H), 2.30(s, 3H), 3.30(s, 2H), 6.95-7.05(m, 1 H), 7.10(d, 2H) ppm.

Comp. 11-41 : ¹H-NMR (400 MHz,CDCI₃): δ = 3.75(s, 2H), 6.85-6.95(m, 1 H), 6.95-7.05(m, 2H), 7.20(d, 1 H), 7.30(dd, 1 H), 7.60(s, 1 H), 7.75(d, 1 H) ppm.

Comp. II-42: ¹H-NMR (400 MHz,CDCI₃): δ = 2.70(s, 3H), 3.60(s, 2H), 6.90-7.00(m, 1 H), 7.05- 7.15(m, 3H) ppm.

Comp. II-43: H-NMR (400 MHz,CDCI₃): δ = 1 .40(d, 6H), 3.15-3.30(m, 1 H), 3.65(s, 2H), 6.90- 7.00(m, 1 H), 7.10-7.20(m, 2H) ppm.

Comp. II-44: H-NMR (400 MHz,CDCI₃): δ = 3.75(s, 2H), 6.90-6.95(m, 1 H), 7.05-7.15(m, 2H), 7.35(d, 1 H), 8.80(d, 1 H) ppm.

Comp. II-45: H-NMR (500 MHz,CDCI₃): δ = 2.65(s, 3H), 3.65(s, 2H), 6.95-7.00(m, 1 H), 7.20(d, 2H) ppm.

Comp. II-46: ¹H-NMR (500 MHz,CDCI₃): δ = 3.60(s, 2H), 3.80(s, 3H), 6.50(s, 1 H), 7.00-7.05(m, 1 H), 7.05-7.15(d, 2H) ppm.

Comp. II-47: ¹H-NMR (500 MHz,CDCI₃): δ = 4.90(s, 2H), 7.00(t, 1 H), 7.10(d, 2H), 8.05(s, 1 H), 8.15(s, 1 H) ppm.

Comp. II-48: ¹H-NMR (400 MHz,CDCI₃): δ = 1 .00-1 .10(m, 2H), 1 .10-1.20(m, 2H), 2.10-2.20(m, 1 H), 3.75(s, 2H), 7.20(t, 2H), 7.55(q, 2H) ppm.

Comp. II-52: ¹H-NMR (400 MHz,CDCI₃): δ = 2.43 (s, 3H), 3.79 (s, 2H), 7.20-7.29 (m, 2H), 7.59- 7.65 (m, 2H) ppm.

Comp. II-53: H-NMR (400 MHz,CDCI₃): δ = 2.45 (s, 3H), 3.80 (s, 2H), 7.29-7.36 (m, 2H) ppm. Comp. II-54: H-NMR (400 MHz,CDCI₃): δ = 2.40 (s, 3H), 3.58 (s, 2H), 6.87 (s, 1 H), 7.18-7.22 (m, 2H), 7.48-7.55 (m, 2H) ppm. Comp. II-55: H-NMR (400 MHz,CDCI₃): δ = 2.42 (s, 3H), 3.59 (s, 2H), 6.95 (s, 1 H), 7.19-7.23 (m, 2H) ppm.

Comp. 11-71 : H-NMR (400 MHz,CDCI₃): δ = 2.55 (s, 3H), 3.76 (s, 2H), 7.14-7.21 (m, 2H), 7.63 (s, 1 H) ppm.

Comp. II-80: ¹H-NMR (500 MHz,CDCI₃): δ = 1.38 (s, 9H), 3.64 (s, 2H), 7.05 (s, 1 H), 7.10-7.17 (m, 2H), 7.46-7.51 (m, 2H) ppm.

Comp. II-82: H-NMR (500 MHz,CDCI₃): δ = 4.14 (s, 2H), 7.19-7.26 (m, 2H), 7.55-7.61 (m, 2H), 9.19 (s, 1 H) ppm. B. Biological examples

The activity of the compounds of formula II of the present invention could be demonstrated and evaluated in biological tests described in the following. If not otherwise specified the test solutions are prepared as follows:

The active compound is dissolved at the desired concentration in a mixture of 1 :1 (vokvol) distilled water : acetone. The test solution is prepared at the day of use and in general at concentrations of ppm (wt vol). B.1 Mediterranean fruitfly (Ceratitis capitata)

For evaluating control of Mediterranean fruitfly (Ceratitis capitata) the test unit consisted of microliter plates containing an insect diet and 50-80 C. capitata eggs. The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 5 μΙ, using a custom built micro atomizer, at two replications. After application, microtiter plates were incubated at about 28 + 1 °C and about 80 + 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed. In this test, the compounds 11-10, II-39, II-46, II-68, II-72 and II-74, respectively, at 2500 ppm showed a mortality of at least 75% in comparison with untreated controls.

B.2 Green Peach Aphid (Myzus persicae) For evaluating control of green peach aphid (Myzus persicae) through systemic means the test unit consisted of 96-well-microtiter plates containing liquid artificial diet under an artificial membrane. The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were pipetted into the aphid diet, using a custom built pipetter, at two replications. After application, 5 - 8 adult aphids were placed on the artificial membrane inside the microtiter plate wells. The aphids were then allowed to suck on the treated aphid diet and incubated at about 23 + 1 °C and about 50 + 5 % relative humidity for 3 days. Aphid mortality and fecundity was then visually assessed. In this test, the compounds II-9, 11-10, 11-1 1 , II-44, II-62, II-63 and II-72, respectively, at a concentration of the test solution of 2500 mg/L showed a mortality of at least 75%.

B.3 Orchid thrips (Dichromothrips corbetti)

Dichromothrips corbetti adults used for bioassay are obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the test compound is diluted to a concentration of 300 ppm (wt compound: vol diluent) in a 1 :1 mixture of acetone:water (vohvol), plus 0.01 % vol/vol Kinetic^® surfactant. Thrips potency of each compound is evaluated by using a floral-immersion technique. Plastic petri dishes are used as test arenas. All petals of individual, intact orchid flowers are dipped into treatment solution and allowed to dry. Treated flowers are placed into individual petri dishes along with 10 - 15 adult thrips. The petri dishes are then covered with lids. All test arenas are held under continuous light and a temperature of about 28°C for duration of the assay. After 4 days, the numbers of live thrips are counted on each flower, and along inner walls of each petri dish. The level of thrips mortality is extrapolated from pre-treatment thrips numbers.

In this test, the compounds 11-31 , II-46 and II-65, respectively, at 500 ppm showed a mortality of at least 75% in comparison with untreated controls.

Additionally, the compounds 11-31 , II-46, II-60, II-63, II-64, II-65, II-67, II-72, II-73, II-74, II-78, II-79 and 11-81 , respectively, at 300 ppm showed a mortality of at least 75% in comparison with untreated controls. B.4 Silverleaf whitefly (Bemisia argentifolii)

The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in 1 .3 ml ABgene® tubes. These tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01 % (v/v). Cotton plants at the cotyledon stage (one plant per pot) were sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into a plastic cup and 10 to 12 whitefly adults (approximately 3-5 days old) were introduced. The insects were collected using an aspirator and 0.6 cm, nontoxic Tygon® tubing (R-3603) connected to a barrier pipette tip. The tip, containing the collected insects, was then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. Cups were covered with a reusable screened lid (150-micron mesh polyester screen PeCap from Tetko, Inc.). Test plants were maintained in a growth room at 25°C and 20-40% relative humidity for 3 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment, compared to untreated control plants. In this test, the compounds 11— 8, II-23, 11-31 , II-38 and II-63, respectively, at 500 ppm showed a mortality of at least 75% in comparison with untreated controls.

B.5 Vetch aphid (Megoura viciae)

For evaluating control of vetch aphid (Megoura viciae) through contact or systemic means the test unit consisted of 24-well-microtiter plates containing broad bean leaf disks. The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the leaf disks at 2.5 μΙ, using a custom built micro atomizer, at two replications. After application, the leaf disks were air-dried and 5 - 8 adult aphids placed on the leaf disks inside the microtiter plate wells. The aphids were then allowed to suck on the treated leaf disks and incubated at about 23 + 1 °C and about 50 + 5 % relative humidity for 5 days. Aphid mortality and fecundity was then visually assessed. In this test, the compounds II-8 and II-67, respectively, at 2500 ppm showed a mortality of at least 75% in comparison with untreated controls.

B.6 Tobacco budworm (Heliothis virescens) I The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01 % (v/v). Cotton plants were grown 2 plants to a pot and selected for treatment at the cotyledon stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into perforated plastic bags with a zip closure. About 10 to 1 1 budworm larvae were placed into the bag and the bags zipped closed. Test plants were maintained in a growth room at about 25°C and about 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the bags. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants.

In this test, the compounds II-9, 11-10, 11-1 1 , 11-13, II-53 and 11-61 , respectively, at 2500 ppm showed a mortality of at least 75% in comparison with untreated controls.

B.7 Boll weevil (Anthonomus grand is)

For evaluating control of boll weevil (Anthonomus grandis) the test unit consisted of 24-well- microtiter plates containing an insect diet and 20-30 A. grandis eggs. The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 20 μΙ, using a custom built micro atomizer, at two replications. After application, microtiter plates were incubated at about 23 + 1 °C and about 50 + 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed.

In this test, the compounds II-8, II-9, 11-10, 11-1 1 , 11-12, 11-13, II-20, II-23, II-24, II-25, II-26, 11-31 , II-32, II-34, II-46, II-50, II-53, II-59, II-60, 11-61 , II-62, II-63, II-65, II-67, II-68, II-69, 11-71 , II-72, II-73 and II-74, respectively, at 2500 ppm showed a mortality of at least 75% in comparison with untreated controls.

B.8 Rice brown plant hopper (Nilaparvata lugens)

Rice seedlings were cleaned and washed 24 hours before spraying. The active compounds were formulated in 50:50 acetone:water (vohvol) and 0.1 % vol/vol surfactant (EL 620) was added. Potted rice seedlings were sprayed with 5 ml test solution, air dried, placed in cages and inoculated with 10 adults. Treated rice plants were kept at about 28-29°C and relative humidity of about 50-60%. Percent mortality was recorded after 72 hours.

In this test, the compounds II-8, II-9, 11-10, 11-1 1 , 11-12, 11-13, 11-16, 11-19, 11-21 , II-22, II-24, II-25, 11-31 , II-34, II-38, II-44, II-46, II-54 and II-55, respectively, at 500 ppm showed a mortality of at least 75% in comparison with untreated controls.

B.9 Yellow fever mosquito (Aedes aegypti)

For evaluating control of yellow fever mosquito (Aedes aegypti) the test unit consisted of 96- well-microtiter plates containing 200μΙ of tap water per well and 5-15 freshly hatched A. aegypti larvae. The compounds or mixtures were formulated using a solution containing 75% water and 25% DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect diet at 2.5μΙ, using a custom built micro atomizer, at two replications. After application, microtiter plates were incubated at 28 + 1 °C, 80 + 5 % RH for 2 days. Larval mortality was then visually assessed.

In this test, the compounds II-3, II-6, II-8, II-9, 11-10, 11-12, 11-13, 11-15, 11-19, II-20, II-32, II-34, II-53, II-59, II-60, 11-61 , II-63, II-67, 11-71 , II-72 and II-74, respectively, at 2500 ppm showed a mortality of at least 75% in comparison with untreated controls. B.10 Green Soldier Stink Bug {Nezara viridula)

The active compound is dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water : acetone. Surfactant (Kinetic HV) is added at a rate of 0.01 % (vol/vol). The test solution is prepared at the day of use. Soybean pods were placed in microwavable plastic cups lined with moist filter paper and inoculated with ten 3rd instar N. viridula. Using a hand atomizer, an approximately 2 ml solution is sprayed into each cup. Treated cups were kept at about 28- 29°C and relative humidity of about 50-60%. Percent mortality was recorded after 5 days. In this test, the compounds II-8 and 11-31 , respectively, at 500 ppm showed a mortality of at least 75% in comparison with untreated controls.

Additionally, the compounds 11-31 , II-59, II-63, II-65, II-67 and II-79, respectively, at 300 ppm showed a mortality of at least 75% in comparison with untreated controls.

Claims

1 . The use of a compound of formula (I)

or a salt thereof for combating animal pests, wherein

Y is phenyl unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituents R⁵; or naphthyl unsubstituted or substituted with 1 , 2, 3, 4, 5, 6 or 7 substituents R⁵;

Q is a 5-membered aromatic heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from N, O, S, wherein the aforementioned ring is unsubstituted or substituted with 1 , 2, 3 or 4 substituents R⁶;

R¹ is hydrogen, halogen, cyano, hydroxy, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3- Cs-cycloalkyl, Cs-Cs-cycloalkenyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, Ci-C6-alkylthio, (C1-C6- alkoxy)carbonyl, wherein the carbon atoms of the aforementioned aliphatic or cycloali- phatic radicals are unsubstituted or substituted with 1 , 2 or 3 substituents R⁷;

R² is hydrogen or halogen; or

R³ is hydrogen, halogen, cyano, hydroxy, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3- Cs-cycloalkyl, Cs-Cs-cycloalkenyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, Ci-C6-alkylthio, (C1-C6- alkoxy)carbonyl, wherein the carbon atoms of the aforementioned aliphatic or cycloali- phatic radicals are unsubstituted or substituted with 1 , 2 or 3 substituents R⁷;

R⁴ is hydrogen or halogen; or

R³ and R⁴ form together with the carbon atom to which they are attached a methylene group or a cyclopropyl group; each R⁵, R⁶ is independently halogen, cyano, azido, nitro, -SCN, SF₅, C1-C6 alkyl, C2- C6 alkenyl, C2-C6 alkynyl, wherein the carbon atoms of the aforementioned aliphatic radicals are unsubstituted or substituted with one or more R^a; C3-C8 cycloalkyl or C3-C8 cycloalkenyl, wherein the carbon atoms of the aforementioned cycloaliphatic radicals are unsubstituted or substituted with one or more R^b;

phenyl unsubstituted or substituted with up to 5 R^c;

a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO,

SO, SO2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R^d; Si(R^e)₃, OR^f, SR^f, OS(0)_xR^h, S(0)_xR^h, ti{R N(Rⁱ)C(=0)R^m, OC(=0)R^m, C(=0)R^m, C(=0)OR^f, C(=NR')R^m, C(=S)R^m;

or

two R⁶ on two adjacent atoms present on one 5-membered aromatic heterocyclic ring form together with the atoms the two R⁶ are bonded to a 5- or 6-membered partially unsaturated or aromatic carbocyclic ring or a 5- or 6-membered partially unsaturated or aro- matic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O, S, wherein the aforementioned carbocyclic or heterocyclic ring is unsubstituted or substituted with 1 or 2 substituents selected from =0, CH3, OCH3, halogen, halomethyl and halomethoxy; each R⁷ is independently halogen, cyano, hydroxy, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkenyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C1-C6- alkylthio, (Ci-C6-alkoxy)carbonyl, OSi(R^e)3, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted, partially or fully halogenated and/or oxygenated; R^aa is -C(=S)N(R^CC)₂, -C(=NR^dd)SR^ee, -C(=0)N(R^ff)₂, or CN;

R^bb is -C(=S)N(R^CC)₂, -C(=NR^dd)SR^ee, -C(=0)N(R^ff)₂, or CN; each R^cc is independently hydrogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C₂-C6-alkenyl, C₂-C6-haloalkenyl, C₂-C6-alkynyl, C₂-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-haloalkoxy-Ci-C6-alkyl, Ci-C6-alkylthio-Ci- Ce-alkyl, Ci-C₆-haloalkylthio-Ci-C₆-alkyl; each R^dd is independently hydrogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C₂-C6-alkenyl, C₂-C6-haloalkenyl, C₂-C6-alkynyl, C₂-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-haloalkoxy-Ci-C6-alkyl, Ci-C6-alkylthio-Ci- Ce-alkyl, Ci-C₆-haloalkylthio-Ci-C₆-alkyl; each R^ee is independently cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci- Ce-alkoxy-CrCe-alkyl, Ci-C₆-haloalkoxy-Ci-C₆-alkyl, Ci-C₆-alkylthio-Ci-C₆-alkyl, Ci-C₆- haloalkylthio-Ci-C6-alkyl; each R^ff is independently hydrogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-haloalkoxy-Ci-C6-alkyl, Ci-C6-alkylthio-Ci- Ce-alkyl, Ci-C₆-haloalkylthio-Ci-C₆-alkyl; each R^a is independently halogen, cyano, azido, nitro, -SCN, SF₅, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyI, Cs-Cs-halocycloalkyI, C2-C6-alkenyl, C2- C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, Ci-C6-alkyl-C3-C8-cycloalkyl,

Si(R^e)₃, OR^A, SR^A, OS0₂R^B, S(0)_xR^B, -S(0)_xN(R^D)₂, N(R^D)₂, C(=0)N(R^D)₂, C(=S)N(R^D)₂,

C(=0)OR^A,

phenyl unsubstituted or substituted with up to 5 R^E;

a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R^E, or

two R^a form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocy- die or heterocyclic ring together with the carbon atoms the two R^a are bonded to; each R^b is independently halogen, cyano, azido, nitro, -SCN, SF₅, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyI, Cs-Cs-halocycloalkyI, C2-C6-alkenyl, C2- C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, Ci-C6-alkyl-C3-C8-cycloalkyl,

Si(R^G)₃, OR^H, SR^H, OS0₂R^J, S(0)_xR^J, -S(0)_xN(R^K)₂, N(R^K)₂, C(=0)N(R^K)₂, C(=S)N(R^K)₂,

C(=0)OR^H,

or

two R^b form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocy- clic or heterocyclic ring together with the carbon atoms the two R^b are bonded to; each R^c is independently halogen, cyano, azido, nitro, -SCN, SF₅, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyI, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R^M; Si(R^G)₃, OR^H, SR^H, OS(0)_xR^J, S(0)_xR^J, -S(0)_xN(R^K)₂, N(R^K)₂, C(=0)R^N, C(=0)OR^H, C(=NR^K)R^N, C(=0)N(R^K)₂, C(=S)N(R^K)₂; each R^d is independently halogen, cyano, azido, nitro, -SCN, SF₅, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R^M; Si(R^G)₃, OR^H, SR^H, OS(0)xR^J, S(0)_xR^J, -S(0)_xN(R^K)₂, N(R^K)₂, C(=0)R^N, C(=0)OR^H,

C(=NR^K)R^N, C(=0)N(R^K)₂, C(=S)N(R^K)₂,

or

two R^d present on one atom of a saturated or partially unsaturated heterocyclic ring are together =0, =C(R^L)₂; =NR^K, =NOR^H or =NN(R^K)₂; each R^e is independently halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C2- C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C8 cycloalkyi, C3-C8 halocycloalkyl, C1-C6 haloalkoxyalkyl,

phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic hetero- cyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S,

NO, SO, S0₂; each R^f is independently hydrogen, cyano, Ci-C6-alkyl, Ci-C6-alkylsulfinyl, C1-C6- alkylsulfonyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R^M;

NO, SO, S0₂; each R^h is independently hydrogen, cyano, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforemen- tioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more

R^M;

N(R^D)₂, -N=C(R^F)₂, C(=0)R^Q, C(=0)N(R^D)₂, C(=S)N(R^D)₂, C(=0)OR^A,

phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, S0₂; each R' is independently hydrogen, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Cs-Cs- cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R^M; S(0)xR^B, -S(0)xN(R^D)₂, C(=0)R^s, C(=0)OR^A, C(=0)N(R^D)₂, C(=S)R^S, C(=S)SR^A,

C(=S)N(R^D)₂, C(=NR^D)R^S,

phenyl unsubstituted or substituted with up to 5 R^E; a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R^E, or

two R' on one nitrogen atom are together a C2-C7 alkylene chain and form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or aromatic ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, and wherein the alkylene chain is unsubstituted or substituted with halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl; each R^m is independently hydrogen, -SCN, SF₅, Ci-C6-alkyl, Ci-C6-alkoxy, C1-C6- alkylthio, Cs-Cs-cycloalkyI, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R^M;

phenyl unsubstituted or substituted with up to 5 R^E;

SO, SO2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R^E; each R^A is independently hydrogen, cyano, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, tri- methylsilyl, triethylsilyl, tert-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyI, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy;

phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy and (Ci-C6-alkoxy)carbonyl; each R^B is independently hydrogen, cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,

phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-Ce- alkyI, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy and (Ci-C6-alkoxy)carbonyl; each R^D is independently hydrogen, cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from Ci-C4-alkoxy;

phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstitut- ed, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy and (Ci-C6-alkoxy)carbonyl, or

two R^D on one nitrogen atom are together a C2-C6 alkylene chain and form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, or 7-membered saturated, partially unsaturated or aromatic ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, and wherein the alkylene chain is unsubstituted or substituted with halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy or C1-C4- haloalkoxy; each R^E is independently cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-

C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert- butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from Ci-C4-alkoxy,

or

two R^E present on one atom of a saturated or partially unsaturated heterocyclic ring are together =0, =N(Ci-C₆-alkyl), =NO(Ci-C₆-alkyl), =CH(Ci-C₄-alkyl) or =C(Ci-C₄-alkyl)Ci-C₄- alkyl; each R^F is independently C1-C4 alkyl, C1-C6 cycloalkyl, C1-C4 alkoxyalkyl, phenyl or benzyl; each R^G is independently halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C2- C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 haloalkoxyalkyl; each R^H is independently hydrogen, cyano, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy; each R^J is independently hydrogen, cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy; each R^K is independently hydrogen, cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, tri- ethylsilyl, tert-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from Ci-C4-alkoxy; each R^L is independently C1-C4 alkyl or C1-C4 alkoxyalkyl; each R^M is independently halogen, cyano, azido, nitro, OH , SH , -SCN , SF₅, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C1-C6- haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyI, Ci-C6-alkyl-C3-C8-cycloalkyl, wherein the five last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy,

or

two R^M present on one carbon atom are together =0, =CH (Ci-C4-alkyl), =C(Ci-C₄- alkyl)Ci-C₄-alkyl, =N(Ci-C₆-alkyl) or =NO(Ci-C₆-alkyl); each R^N is independently hydrogen, OH , SH , -SCN , SF₅, d-C₆-alkoxy, Ci-C₆- haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy; each R^Q is independently hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert- butyldimethylsilyl,

phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-Ce- alkyI, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy and (Ci-C6-alkoxy)carbonyl; each R^s is independently hydrogen, OH , SH , -SCN , SF₅, Ci-C6-alkoxy, C1-C6- haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyI, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, (Ci-C6-alkoxy)carbonyl, (C1-C6- alkyl)amino and di-(Ci-C6-alkyl)amino; p is O or l ; x is 1 or 2.

The use according to claim 1 , wherein

Y is phenyl unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituents R⁵; or naph- thyl unsubstituted or substituted with 1 or 2 substituents R⁵;

Q is a 5-membered aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O, S, wherein the aforementioned ring is unsubstituted or substituted with 1 , 2 or 3 substituents R⁶;

R¹ is H, halogen, cyano, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or (Ci -Ce-aI koxy)ca rbonyl ,

wherein the five radicals last mentioned are unsubstituted or substituted with 1 , 2 or 3 substituents selected from halogen, cyano, hydroxy, OSi(Ci-C6-alkyl)3, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, Ci-C6-alkoxy and (Ci-C6-alkoxy)carbonyl, wherein the six radicals last mentioned are unsubstituted or partially or fully halogenated; R² is H or halogen;

or

R¹ and R² form together with the carbon atom to which they are attached a methylene group;

R³ is H, halogen, cyano, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or (Ci -Ce-aI koxy)ca rbonyl ,

wherein the five radicals last mentioned are unsubstituted or substituted with 1 , 2 or 3 substituents selected from halogen, cyano, hydroxy, OSi(Ci-C6-alkyl)3, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, Ci-C6-alkoxy and (Ci-C6-alkoxy)carbonyl, wherein the six radicals last mentioned are unsubstituted or partially or fully halogenated; R⁴ is H or halogen;

or

R³ and R⁴ form together with the carbon atom to which they are attached a methylene group;

R⁵ is halogen, cyano, SF₅, tri-(Ci-C4-alkyl)silyl-C2-C4-alkynyl, (C1-C6- alkyl)aminocarbonyl, di-(Ci-C6-alkyl)aminocarbonyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, C1-C6- alkylsulfonyl, (Ci-C6-alkoxy)carbonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (C1-C6- alkyl)carbonyl or (Ci-C6-alkyl)carbonyloxy, wherein the 14 radicals last mentioned are unsubstituted or substituted with one or more substituents selected from halogen, cyano, Ci-C4-alkyl-C3-C6-cycloalkyl, Ci-C6-alkyl, C2- C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl and Ci-C6-alkoxy,

R⁶ is halogen, nitro, cyano, SF₅, tri-(Ci-C4-alkyl)silyl-C2-C4-alkynyl, 2,2,2-trifluoro-1 - hydroxy-1 -(trifluoromethyl)ethyl, (Ci-C6-alkyl)aminocarbonyl, di-(Ci-C6- alkyl)aminocarbonyl, dimethylcarbamoylsulfanyl, morpholine-4-carbonyl, acetamido, pyridyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, C3-C6-alkynyloxy, C3-C6-cycloalkoxy, phenoxy, Ci- C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, (Ci-C6-alkoxy)carbonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl or (Ci-C6-alkyl)carbonyloxy, wherein the 17 radicals last mentioned are unsubstituted or substituted with one or more substituents selected from halogen, cyano, Ci-C4-alkyl-C3-C6-cycloalkyl, Ci-C6-alkyl, C2- C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl and Ci-C6-alkoxy,

two R⁶ on two adjacent atoms present on one 5-membered aromatic heterocyclic ring are together a bridge selected from CH=CH-CH=CH, N=CH-CH=CH, N=CH-CH=N,

OCH2CH2O, 0(CH2)0 and form together with the atoms the two R⁶ are bonded to a 5- or 6-membered partially unsaturated or aromatic carbocyclic or heterocyclic ring, wherein the ring is unsubstituted;

R^aa is -C(=S)N(R^CC)₂, -C(=0)N(R^ff)₂, or CN;

R^bb is CN;

p is O or l .

The use according to claim 1 or 2, wherein

R is H, Me, Et, iPr, cPr, CH₂CN, CF₃, CHF₂, CH₂F, CH₂CH₂F, CH₂CHF₂, CH2CF3, CN, halogen, CH₂OH, CH₂OMe, CH₂OEt, C0₂Me, C0₂Et, CH₂C0₂Me, CH₂C0₂Et,

CH₂OSi(Me)₃ or CH₂OSi(Et)₃.

The use according to any one of claims 1 to 3, wherein

R³ is H, Me, Et, iPr, cPr, CH₂CN, CF₃, CHF₂, CH₂F, CH₂CH₂F, CH₂CHF₂, CH2CF3, CN, halogen, CH₂OH, CH₂OMe, CH₂OEt, C0₂Me, C0₂Et, CH₂C0₂Me, CH₂C0₂Et,

CH₂OSi(Me)₃ or CH₂OSi(Et)₃. The use according to any one of claims 1 to 4, wherein

R⁵ is halogen, Me, Et, iPr, cPr, OMe, OEt, OiPr, ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, CN, CF₃, OCFs, SF₅, CHF₂, OCHF₂, SMe, S(0)Me, S(0)₂Me, SCF₃, S(0)CF₃, S(0)₂CF₃, SCHF₂, S(0)CHF₂, S(0)₂CHF₂, C0₂Me, C0₂Et, C(0)Me, OAc, C(0)NHMe, C(0)NMe₂, CH₂OMe or CH₂OEt;

or

two R⁵ on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from N=CH-CH=CH, N=CH-CH=N, OCH₂CH₂0, 0(CH₂)0 and form together with the carbon atoms the two R⁵ are bonded to a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring, wherein the ring is unsubstituted.

The use according to any one of claims 1 to 5, wherein

R⁶ is halogen, Me, Et, iPr, cPr, tBu, OMe, OEt, OiPr, OtBu, ethynyl, (trimethylsi- lyl)ethynyl, vinyl, Ph, N0₂, CN, CF₃, OCF₃, SF₅, CHF₂, OCHF₂, SMe, S(0)Me, S(0)₂Me, SCF₃, S(0)CF₃, S(0)₂CF₃, SCHF₂, S(0)CHF₂, S(0)₂CHF₂, C0₂Me, C0₂Et, C0₂iPr, C(0)Me, OAc, C(0)NHMe, C(0)NMe₂, CH₂OMe, CH₂OEt, 2,2,2-trifluoroethyl, 1 ,2,2,2- tetrafluoro-1 -(trifluoromethyl)ethyl, 2,2,2-trifluoro-1-hydroxy-1 -(trifluoromethyl)ethyl, di- methoxymethyl, 2,2,2-trifluoroethoxy, 2,2-difluorocyclopropoxy, tert-butylsulfanyl, dime- thylcarbamoylsulfanyl, morpholine-4-carbonyl, acetamido or prop-2-ynoxy;

or

The use according to claim 1 or 2, wherein

Y is phenyl unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituents R⁵; or naphthyl unsubstituted or substituted with 1 substituent R⁵;

Q is pyrrolyl, furanyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl or thiadiazolyl, wherein the aforementioned rings are unsubstituted or substituted with 1 , 2 or 3 substituents R⁶;

R is H, Me, Et, CN, CH₂CN, CH₂CF₃, halogen, CH₂OH, CH₂OMe, CH₂OEt,

CH₂C0₂Me, CH₂C0₂Et, CH₂OSi(Me)₃ or CH₂OSi(Et)₃;

R² is H or halogen;

R³ is H, Me, Et, CN, CH₂CN, CH₂CF₃, halogen, CH₂OH, CH₂OMe, CH₂OEt,

CH₂C0₂Me, CH₂C0₂Et, CH₂OSi(Me)₃ or CH₂OSi(Et)₃;

R⁴ is H or halogen;

R⁵ is halogen, cyano, tri-(Ci-C4-alkyl)silyl-C₂-C4-alkynyl, Ci-C6-alkyl, C₂-C6-alkenyl, C₂- C6-alkynyl, C₃-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, Ci-C6-alkylthio or (C1-C6- alkoxy)carbonyl, wherein the eight radicals last mentioned are unsubstituted or partially or fully halogenat- ed;

or

two R⁵ on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from N=CH-CH=CH, N=CH-CH=N, OCH₂CH₂0, 0(CH₂)0 and form together with the carbon atoms the two R⁵ are bonded to a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring, wherein the ring is unsubstituted;

R⁶ is halogen, nitro, cyano, tri-(Ci-C4-alkyl)silyl-C2-C4-alkynyl, 2,2,2-trifluoro-1 -hydroxy- 1 -(trifluoromethyl)ethyl, dimethoxymethyl, dimethylcarbamoylsulfanyl, morpholine-4- carbonyl, acetamido, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, C3-C6-alkynyloxy, C3-C6-cycloalkoxy, phenoxy, Ci-C6-alkylthio, C1-C6- alkylsulfonyl or (Ci-C6-alkoxy)carbonyl,

wherein the twelve radicals last mentioned are unsubstituted or partially or fully halogen- ated;

or

two R⁶ on two adjacent atoms present on one 5-membered aromatic heterocyclic ring are together a bridge selected from CH=CH-CH=CH and form together with the atoms the two

R⁶ are bonded to a 6-membered aromatic carbocyclic or heterocyclic ring, wherein the ring is unsubstituted;

R^aa is -C(=S)N(R^cc)₂ or CN;

R^bb is CN;

each R^cc is independently H, Me, Et, propargyl, allyl, CH₂OMe or CH₂OEt;

p is O or l .

The use according to any one of claims 1 to 7, wherein

R⁵ is halogen, Me, OMe, CN, CF₃, OCF₃ or ethynyl.

The use according to any one of claims 1 to 8, wherein

R⁶ is halogen, Me, OMe, CN, CF₃, OCF₃, ethynyl or prop-2-ynoxy.

0. The use according to any one of claims 1 , 2 or 7, wherein

Y is phenyl unsubstituted or substituted with 1 , 2 or 3 substituents R⁵;

Q is pyrrolyl, furanyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl or thiadiazolyl, wherein the aforementioned rings are unsubstituted or substituted with 1 or 2 substituents R⁶;

R is H, F, Me, Et, CN, CH₂CN or CH₂OMe;

R⁵ is F, CI, Br or CF₃;

R⁶ is F, ethynyl, prop-2-ynoxy or CF₃;

R^aa is -C(=S)NH₂ or CN;

R^bb is CN;

p is 0.

1 1 . The use according to any one of claims 1 to 10, wherein R¹ is H.

12. The use according to any one of claims 1 to 9, 1 1 , wherein R³ is H.

13. The use according to any one of claims 1 to 3, 5 to 1 1 , wherein p is 0.

14. The use according to any one of claims 1 to 13, with the proviso that R^cc is H when R^aa or R^bb is CN.

15. The use according to any one of claims 1 to 14, wherein R^aa is -C(=S)NH2 or CN; and R^bb is CN.

16. The use according to any one of claims 1 to 15, wherein R^aa is -C(=S)NH2; and R^bb is CN.

17. The use according to any one of claims 1 to 15, wherein R^aa is CN; and R^bb is CN.

18. The use according to any one of claims 1 to 3, 5 to 1 1 , 13 to 17, wherein R¹ and R² are H; and p is 0.

19. An agricultural and/or veterinary composition comprising at least one compound of formula (I) according to any one of claims 1 to 18 or a salt thereof.

20. The composition according to claim 19, which further comprises at least one inert liquid and/or at least one solid carrier.

21 . A method for combating animal pests, which comprises contacting the animal pests, their habit, breeding ground, food supply, plant, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one compound of formula (I) according to any one of claims 1 to 18 or a salt thereof.

22. A method for protecting crops from attack or infestation by animal pests, which comprises contacting the crop with a pesticidally effective amount of at least one compound of formula (I) according to any one of claims 1 to 18 or a salt thereof.

23. A method for protecting seeds from soil insects and the seedlings' roots and shoots from soil and foliar insects, which comprises contacting the seeds before sowing and/or after pregermination with at least one compound of formula (I) according to any one of claims 1 to 18 or a salt thereof.

24. Seeds comprising at least one compound of formula (I) according to any one of claims 1 to 18 or a salt thereof.

The use of a compound of formula (I) according to any one of claims 1 to 18 or a salt thereof for combating parasites in and on animals.

A method for treating or protecting animals against infestation or infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of at least one compound of formula (I) according to any one of claims 1 to 18 or a salt thereof.

A method for the preparation of a composition for treating or protecting animals against infestation or infection by parasites, which comprises mixing a parasiticidally effective amount of at least one compound of formula (I) according to any one of claims 1 to 18 or a salt thereof and at least one solid carrier.

28. The use of a compound of formula (I) according to any one of claims 1 to 18 or a salt thereof for the preparation of a medicament for treating or protecting animals against infestation or infection by parasites.

29. A compound of formula (I) according to any one of claims 1 to 18 or a salt thereof, with the proviso that R^cc is H when R^aa or R^bb is CN.

30. The compound according to claim 29, wherein R^aa is -C(=S)NH₂ or CN; and R^bb is CN.

31 . The compound according to claim 29 or 30, wherein R^aa is -C(=S)NH₂; and R^bb is CN.

The compound according to claim 29 or 30, wherein R^aa is CN; and R^bb is CN.

A compound of formula (I) according to any one of claims 29 to 32 or a salt thereof as medicament.

A method for preparing a compound of formula (I) according to any one of claims 1 to 15, 17, 18, 29, 30, 32, 33 or a salt thereof, wherein R^aa is CN, and R^bb is CN, comprising the step of reacting a compound of formula (XXI),

wherein Y is defined as in formula (I); with a compound of formula (XXII),

wherein R¹, R², R³, R⁴, Q and p are defined as in formula (I); and

L is a leaving group; optionally in the presence of a base.

A method for preparing a compound of formula (I) according to any one of claims 1 to 16, 18, 29 to 31 , 33 or a salt thereof, wherein R^aa is -C(=0)N(R^ff)₂; and R^bb is -C(=0)N(R^ff)₂ or CN; or wherein R^aa is -C(=S)N(R^CC)₂; and R^bb is -C(=S)N(R^CC)₂ or CN; comprising the steps of

(i) reacting a compound of formula (XI),

wherein Y is defined as in formula (I);

R^aa* is -C(=0)0(Ci-C₄-alkyl);

R ^* is -C(=0)0(Ci-C₄-alkyl) or CN,

provided that R^bb* is CN when R^bb is CN; with a compound of formula (XII),

wherein R¹, R², R³, R⁴, Q and p are defined as in formula (I);

wherein R¹, R², R³, R⁴, Y, Q and p are defined as in formula (I);

R^aa* and R^bb* are defined as in formula (XI);

(ii) reacting the compound of formula (XIII) with an amine of formula (XIV),

wherein R¹, R², R³, R⁴, Y, Q and p are defined as in formula (I);

R^aa- is -C(=0)N(R^cc)₂;

R^bb** i_S -C(=0)N(R^cc)₂ or CN,

wherein R^cc is defined as in formula (I);

(iii) converting the compound of formula (XV) to a compound of formula (I), wherein R is -C(=S)N(R^CC)₂; and R is -C(=S)N(R^CC)₂ or CN.