Isothiazoline compounds for combating invertebrate pests

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

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

Related insecticidal aryl azoline compounds are described in WO 201 1/092287, WO 201 1/073444, WO 2010/090344, WO 2009/1 12275 and WO 97/23212. However, these documents do not describe compounds having the characteristic substituents and substituents' arrangement as claimed in the present invention.

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

The object of the present invention was moreover to provide compounds which are less persistent, bioaccumulative and/or toxic than the compounds of the prior art. Especially isoxazoline insecticides show a high persistency in the soil and thus accumulate there. It has been found that these objectives can be achieved by isothiazoline compounds of the formula I below, by their steroisomers and by their salts, in particular their agriculturally or veterinarily acceptable salts.

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

wherein

A is a group A ¹ , A ² , A ³ or A ⁴ ;

wherein

A ¹ is selected from the group consisting of -C(=NR ⁶ )R ⁸ , -S(0) _n R ⁹ and

-N(R ⁵ )R ⁶ ; A ² is a group of following formula:

wherein

# denotes the bond to the aromatic ring of formula (I);

W is selected from O and S;

Y is selected from hydrogen, -N(R ⁵ )R ⁶ and -OR ⁹ ; is a group of following formula:

wherein

# denotes the bond to the aromatic ring of formula (I); is a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2, 3 or 4 heteroa- toms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, or is a 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring containing 1 , 2, 3 or 4 heteroa- toms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic or heterobicyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substitu- ents R ¹¹ ;

B ¹ , B ² and B ³ are each independently selected from the group consisting of N and CR ² , with the proviso that at most two of B ¹ , B ² and B ³ are N;

G ¹ , G ² , G ³ and G ⁴ are each independently selected from the group consisting of N and CR ⁴ , with the proviso that at most two of G ¹ , G ² , G ³ and G ⁴ are N;

R ¹ is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl-, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl and -C(=0)OR ¹⁵ ; each R ² is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, -SF ₅ , Ci-C6-alkyl, C ₃ -C8-cycloalkyl, C2-C6-alkenyl, C2- C6-alkynyl, wherein the four last mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ⁸ ,

-Si(R ¹² ) ₃ , -OR ⁹ , -S(0) _n R ⁹ , -NR ^10a R ^10b ,

phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R ¹¹ , and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heteromono- or heterobicyclic ring may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ¹¹ ;

R ^3a , R ^3b are each independently selected from the group consisting of hydrogen, halogen, -C0 ₂ R ^3d , hydroxyl, Ci-C ₃ -alkyl, d-C ₃ -haloalkyl, C ₂ -C ₃ -alkenyl, C ₂ -C ₃ - alkynyl, Ci-C ₃ -alkoxy, Ci-C ₃ -haloalkoxy, Ci-C ₃ -alkylthio, Ci-C ₃ -haloalkylthio, Ci- C ₃ -alkylsulfonyl and Ci-C ₃ -haloalkylsulfonyl; or

R ^3a and R ^3b together form a group =0, =C(R ^3c ) ₂ , =NOH or =NOCH ₃ ; is independently selected from the group consisting of hydrogen, halogen, and CF ₃ ; is selected from the group consisting of hydrogen, Ci-C6-alkyl and C1-C3- alkyloxy-Ci-C3-alkyl-;

R ⁴ is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, -SF ₅ , Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ⁸ , Cs-Cs-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ⁸ , C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ⁸ , C2- C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ⁸ ,

-Si(R ¹² ) ₃ , -OR ⁹ , -S(0) _n R ⁹ , -NR ^10a R ^10b ,

phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R ¹¹ , and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ¹¹ ; each R ⁵ is independently selected from the group consisting of hydrogen, C1-C10- alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last- mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ⁸ , and

-S(0) _n R ⁹ , each R ⁶ is independently selected from the group consisting of hydrogen, cyano, Ci- Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last- mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ⁸ ,

-OR ⁹ , -NR ^10a R ^10b , -S(0) _n R ⁹ , -C(=O)NR ^0a N(R ^0a R ^0b ), -Si(R ¹² ) ₃ , -C(=0)R ⁸ , phenyl which may be substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular 1 , substituents R ¹¹ , and

a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substit- uents R ¹¹ ; or R ⁵ and R ⁶ , together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, where the ring may further contain 1 , 2, 3 or 4 heteroa- toms or heteroatom-containing groups selected from O, S, N, SO, SO2, C=0 and C=S as ring members, wherein the heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, wherein the aliphatic or cycloaliphatic moieties in the twelve last- mentioned radicals may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ⁸ , and phenyl which may be substituted with 1 , 2, 3, 4 or 5 substituents R ¹¹ : or R ⁵ and R ⁶ together form a group =C(R ⁸ ) ₂ , =S(0) _m (R ⁹ ) ₂ , =NR ^10a or =NOR ⁹ ;

R ^7a , R ^7b are each independently selected from the group consisting of hydrogen, halogen, cyano, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ⁸ ; each R ⁸ is independently selected from the group consisting of cyano, azido, nitro, - SCN, -SF ₅ , C3-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, where the cycloaliphatic moieties in the two last-mentioned radicals may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ¹³ ;

-Si(R ¹² ) ₃ , -OR ⁹ , -OSO2R ⁹ , -S(0) _n R ⁹ , -N(R ^0a )R ^0b , -C(=O)N(R ^0a )R ^0b ,

-C(=S)N(R ^0a )R ^0b , -C(=0)OR ⁹ ,

phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ , and

a 3-, 4-, 5-, 6- or 7- membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ , or

two R ⁸ present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyi group together form a group =0,

=S(0) _m R ¹⁵ N(R ^4a )R ^4b , =NR ^0a , =NOR ⁹ ; or =NN(R ^0a )R ^0b ;

or

two radicals R ⁸ , together with the carbon atoms of an alkyl, alkenyl, alkynyl or cycloalkyi group which they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, where the heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2, as ring members, and where the carbocyclic or heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ ; and

R ⁸ as a substituent on a cycloalkyi ring is additionally selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl and C2-C6-haloalkynyl, where the aliphatic moieties in these six radicals may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ¹³ ; and

R ⁸ in the groups -C(=NR ⁶ )R ⁸ , -C(=0)R ⁸ and =C(R ⁸ ) ₂ is additionally selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl, where the aliphatic moieties in the six last-mentioned radicals may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ¹³ ;

R ⁹ is independently selected from the group consisting of hydrogen, cyano, Ci- Ce-alkyl, Ci-C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkyl-Ci-C ₄ -alkyl-, C ₃ -C ₈ - halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cydoaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ³ ,

-Ci-C ₆ -alkyl-C(=0)OR ¹⁵ , -Ci-C ₆ -alkyl-C(=0)N(R ^a )R ,

-Ci-C ₆ -alkyl-C(=S)N(R ^4a )R ^4b , -Ci-C ₆ -alkyl-C(=NR ⁴ )N(R ^4a )R ⁴ ,

-Si(R ¹² ) ₃ , -S(0) _n R ¹⁵ , -S(0) _n N(R ^a )R , -N(R ^0a )R ⁰ , -N=C(R ¹³ ) ₂ , -C(=0)R ¹³ , -C(=0)N(R ^4a )R ⁴ , -C(=S)N(R ^4a )R ⁴ , -C(=0)OR ¹⁵ ,

phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ ; and

a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ ; and

R ⁹ in the groups -S(0) _n R ⁹ and -OSO2R ⁹ is additionally selected from the group consisting of Ci-C6-alkoxy and Ci-C6-haloalkoxy;

, R ^10b are selected independently from one another from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2- C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more radicals R ¹³ ; Ci-C ₆ -alkyl-C(=0)OR ¹⁵ , Ci-C ₆ -alkyl- C(=0)N(R ^a )R , -Ci-C ₆ -alkyl-C(=S)N(R ^a )R , -Ci-C ₆ -alkyl- C(=NR )N(R ^a )R , d-Ce-alkoxy, Ci-C ₆ -haloalkoxy, Ci-C ₆ -alkylthio, Ci-C ₆ - haloalkylthio,

-S(0) _n R ¹⁵ , -S(0) _n N(R ^a )R , -C(=0)R ¹³ , -C(=0)OR ¹⁵ , -C(=0)N(R ^a )R , -C(=S)R ¹³ , -C(=S)SR ¹⁵ , -C(=S)N(R ^4a )R ⁴ , -C(=NR ⁴ )R ¹³ ;

phenyl, optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ ; and

a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ ;

or

R ^10a and R ^10b form together with the nitrogen atom they are bonded to a 3-, 4- , 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more, preferably 1 , 2 or 3, in particular 1 , substituents selected from halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ , and a 3-, 4-, 5-, 6,- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ ; or R ^0a and R ¹⁰ together form a group =C(R ¹³ ) ₂ , =S(0) _m (R ¹⁵ ) ₂ ,

=S(0) _m R ¹⁵ N(R ^4a )R ⁴ , =NR ¹⁴ or =NOR ¹⁵ ; is independently selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF ₅ , Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be par- tially or fully halogenated and/or may be substituted with one or more, preferably

1 , 2 or 3, in particular 1 , radicals R ⁸ ,

-OR ⁹ , -NR ^10a R ^10b , -S(0) _n R ⁹ , -Si(R ¹² ) ₃ ;

phenyl, optionally substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular 1 , substituents selected independently from R ¹⁶ ; and

a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated aromatic heterocyclic ring comprising 1 , 2, 3 or 4 heteroatoms or het- eroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents selected independently from R ¹⁶ ;

or two R ¹¹ present on the same ring carbon atom of an unsaturated or partially unsaturated heterocyclic ring may together form a group =0, =S;

=S(0) _m (R ¹⁵ ) ₂ ; =S(0) _m R ¹⁵ N(R ^4a )R ^4b , =NR ¹⁴ , =NOR ¹⁵ , or =NN(R ^4a )R ^4b ;

or two R ¹¹ bound on adjacent ring atoms form together with the ring atoms to which they are bound a saturated 3-, 4-, 5-, 6-, 7-, 8- or 9-membered ring, where- in the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from

O, S, N, NR ¹⁴ , NO, SO and S0 ₂ and/or 1 or 2 groups selected from C=0, C=S and C=NR ¹⁴ as ring members, and wherein the ring may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, d-Ce-alkylthio, Ci-C ₆ -haloalkylthio, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -halocycloalkyl, C ₂ -C ₆ - alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R ¹⁶ , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ¹⁶ ;

R ¹² is independently selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkoxy-Ci-C6- alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-haloalkoxy-Ci- C6-alkyl, and phenyl, optionally substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, preferably 1 or 2, in particular 1 , substituents R ¹⁶ ;

R ¹³ is independently selected from the group consisting of cyano, nitro, -OH, -SH, -SCN, -SF ₅ , d-Ce-alkoxy, Ci-C ₆ -haloalkoxy, Ci-C ₆ -alkylthio, Ci-C ₆ - haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci- C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, ferf-butyldimethylsilyl,

Cs-Cs-cycloalkyI which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from Ci-C4-alkyl, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo; phenyl, benzyl, phenoxy, where the phenyl moiety in the three last-mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, in particular 1 , substituents R ¹⁶ ; and a 3-, 4-, 5-, 6- or 7- membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by 1 , 2 or 3, preferably 1 or 2, in particular 1 , substituents R ¹⁶ ;

or

two R ¹³ present on the same carbon atom (of an alkyl, alkenyl, alkynyl or cycloal- kyl group) may together be =0, =CH(Ci-C ₄ -alkyl), =C(Ci-C ₄ -alkyl)Ci-C ₄ -alkyl, =N(Ci-C ₆ -alkyl) or =NO(Ci-C ₆ -alkyl);

and

R ¹³ as a substituent on a cycloalkyl ring is additionally selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the three last- mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , substituents selected from CN, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo;

and

R ³ in the groups =C(R ¹³ ) ₂ , -N=C(R ¹³ ) ₂ , -C(=0)R ¹³ , -C(=S)R ¹³ and

-C(=NR ¹⁴ )R ¹³ is additionally selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the three last- mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from CN, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo;

R ¹⁴ is independently selected from the group consisting of hydrogen, cyano, Ci C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from CN , Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, C3-C4- cycloalkyl which may be substituted by 1 or 2, in particular 1 , substituents selected from halogen and cyano; and oxo;

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

phenyl, benzyl, pyridyl, phenoxy, wherein the cyclic moieties in the four last- mentioned radicals may be unsubstituted and/or carry 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy,

Ci-C6-haloalkoxy and (Ci-C6-alkoxy)carbonyl; and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 or 2 heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more substituents R ¹⁶ ;

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

R ^14a and R ^14b , together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more, preferably 1 , 2 or 3, in particular 1 , substitutents selected from halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;

or

R ^14a and R ¹⁴ or R ^14b and R ¹⁴ , together with the nitrogen atoms to which they are bound in the group -C(=N R ¹⁴ )N(R ^14a ) R ^14b , form a 3-, 4-, 5-, 6- or 7-membered partially unsaturated or maximally unsaturated heterocyclic ring, wherein the het- erocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more, preferably 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy; R ¹⁵ is independently selected from the group consisting of hydrogen, cyano, trimethylsilyl, triethylsilyl, ferf-butyldimethylsilyl,

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

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

R ¹⁶ is independently selected from the group consisting of halogen, nitro, cyano, -OH, -SH, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci- C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl;

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

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

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

or

two R ¹⁶ present together on the same atom of an unsaturated or partially unsaturated ring may be =0, =S, =N(Ci-C ₆ -alkyl), =NO(Ci-C ₆ -alkyl), =CH(Ci-C ₄ -alkyl) or =C(Ci-C ₄ -alkyl)Ci-C ₄ -alkyl;

or

two R ¹⁶ on two adjacent carbon atoms form together with the carbon atoms they are bonded to a 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, wherein the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, and wherein the ring optionally carries one or more, preferably 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci- C4-haloalkoxy; each n is independently 0, 1 or 2; and

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

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

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

The present invention also relates to plant propagation material, in particular seed, comprising at least one compound of formula I and/or an agriculturally acceptable salt thereof as defined herein.

The present invention further relates to a method for treating or protecting an animal from infestation or infection by parasites which comprises bringing the animal in contact with a parasiticidally effective amount of a compound of the formula I or a veterinarily acceptable salt thereof as defined herein. Bringing the animal in contact with the compound I, its salt or the veterinary composition of the invention means applying or administering it to the animal. The term "steroisomers" encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers). Depending on the substitution pattern, the compounds of the formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. One center of chirality is the carbon ring atom of the isothiazoline ring carrying radical R ¹ . The invention provides both the pure enantiomers or diastereomers and their mixtures and the use according to the invention of the pure enantio- mers or diastereomers of the compound I or its mixtures. Suitable compounds of the formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof.

The term N-oxides relates to a form of compounds I in which at least one nitrogen atom is present in oxidized form (as NO).

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

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

Suitable agriculturally acceptable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH ⁴⁺ ) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy- Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammo- nium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetrae- thylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxy- ethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzl-triethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.

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

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

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

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

The term "non-cultivated plants" refers to any wild type species or related species or related genera of a cultivated plant.

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

http://www.bio.org/speeches/pubs/er/agri_products.asp). Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties. Plants that have been modified by breeding, mutagenesis or genetic engineering, e. g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxyl- phenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made re- sistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1 185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield ^® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g. imazamox, or ExpressSun ^® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g. tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady ^® (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance ^® (imidazolinone tolerant, BASF SE, Germany) and Lib- ertyLink ^® (glufosinate-tolerant, Bayer CropScience, Germany).

Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as δ - endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp. or Xenorhab- dus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomy- cetes 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 ex- pressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701 ). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard ^® (corn cultivars producing the CrylAb toxin), YieldGard ^® Plus (corn cultivars producing Cry1 Ab and Cry3Bb1 toxins), Starlink ^® (corn cultivars producing the Cry9c toxin), Her- culex ^® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphino- thricin-N-Acetyltransferase [PAT]); NuCOTN ^® 33B (cotton cultivars producing the Cry1 Ac toxin), Bollgard ^® I (cotton cultivars producing the Cry1 Ac toxin), Bollgard ^® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT ^® (cotton cultivars producing a VIP-toxin); NewLeaf ^® (potato cultivars producing the Cry3A toxin); Bt- Xtra ^® , NatureGard ^® , KnockOut ^® , BiteGard ^® , Protecta ^® , Bt1 1 (e. g. Agrisure ^® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsan- to Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme). Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called " pathogenesis-related proteins" (PR proteins, see, e. g.

EP-A 392 225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications men- tioned above.

Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), toler- ance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.

Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health- promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera ^® rape, DOW Agro Sciences, Canada).

Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora ^® potato, BASF SE, Germany). The organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix C _n -C _m indicates in each case the possible number of carbon atoms in the group. The term halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.

The term "alkyl" as used herein and in the alkyl moieties of alkoxy, alkylthio, alkylsulfi- nyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl and the like refers to saturated straight- chain or branched hydrocarbon radicals having 1 to 2 ("Ci-C2-alkyl"), 1 to 3 ("C1-C3- alkyl"),1 to 4 ("Ci-C ₄ -alkyl"), 1 to 6 ("Ci-C ₆ -alkyl"), 1 to 8 ("Ci-C ₈ -alkyl") or 1 to 10 ("Ci- Cio-alkyl") carbon atoms. Ci-C2-Alkyl is methyl or ethyl. Ci-C3-Alkyl is additionally propyl and isopropyl. Ci-C ₄ -Alkyl is additionally butyl, 1 -methylpropyl (sec-butyl), 2- methylpropyl (isobutyl) or 1 ,1 -dimethylethyl (tert-butyl). Ci-C6-Alkyl is additionally also, for example, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 - ethylpropyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1 -methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2- ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl, or 1 - ethyl-2-methylpropyl. Ci-Cs-Alkyl is additionally also, for example, heptyl, octyl, 2- ethylhexyl and positional isomers thereof. Ci-Cio-Alkyl is additionally also, for example, nonyl, decyl and positional isomers thereof.

The term "haloalkyl" as used herein, which is also expressed as "alkyl which is partially or fully halogenated", refers to straight-chain or branched alkyl groups having 1 to 2 ("Ci-C ₂ -haloalkyl"), 1 to 3 ("Ci-C ₃ -haloalkyl"), 1 to 4 ("Ci-C ₄ -haloalkyl"), 1 to 6 ("Ci-C ₆ - haloalkyl"), 1 to 8 ("Ci-C ₈ -haloalkyl") or 1 to 10 ("Ci-Cio-haloalkyl") carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: in particular Ci-C2-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluorome- thyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 - chloroethyl, 1 -bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2- fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl. Ci-C3-haloalkyl is additionally, for example, 1 -fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1 ,1 -difluoropropyl, 2,2- difluoropropyl, 1 ,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoro- propyl, 1 ,1 ,1 -trifluoroprop-2-yl, 3-chloropropyl and the like. Examples for C1-C4- haloalkyl are, apart those mentioned for Ci-C3-haloalkyl, 4-chlorobutyl and the like.

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

The term "alkenyl" as used herein refers to monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 ("C2-C3-alkenyl"), 2 to 4 ("C ₂ -C4-alkenyl"), 2 to 6 ("C ₂ -C ₆ -alkenyl"), 2 to 8 ("C ₂ -C ₈ -alkenyl") or 2 to 10 ("C ₂ -Cio-alkenyl") carbon atoms and a double bond in any position, for example C ₂ -C3-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl or 1 -methylethenyl; C ₂ -C4-alkenyl, such as ethenyl, 1 -propenyl,

2- propenyl, 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2- methyl-1 -propenyl, 1 -methyl-2-propenyl or 2-methyl-2-propenyl; C ₂ -C6-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl, 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 - methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl, 1 - pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl-1 -butenyl, 2-methyl-1 -butenyl, 3- methyl-1 -butenyl, 1 -methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1 -methyl-

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

2,2-dimethyl-3-butenyl, 2, 3-dimethyl-1 -butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3- butenyl, 3, 3-dimethyl-1 -butenyl, 3,3-dimethyl-2-butenyl, 1 -ethyl-1 -butenyl, 1 -ethyl-2- butenyl, 1 -ethyl-3-butenyl, 2-ethyl-1 -butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1 ,1 ,2- trimethyl-2-propenyl, 1 -ethyl-1 -methyl-2-propenyl, 1 -ethyl-2-methyl-1 -propenyl, 1 -ethyl- 2-methyl-2-propenyl and the like, or C ₂ -Cio-alkenyl, such as the radicals mentioned for C ₂ -C6-alkenyl and additionally 1 -heptenyl, 2-heptenyl, 3-heptenyl, 1 -octenyl, 2-octenyl, 3-octenyl, 4-octenyl, 1 -nonenyl, 2-nonenyl, 3-nonenyl, 4-nonenyl, 1 -decenyl, 2-decenyl, 3-decenyl, 4-decenyl, 5-decenyl and the positional isomers thereof. The term "haloalkenyl" as used herein, which is also expressed as "alkenyl which is partially or fully halogenated", refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 ("C ₂ -C ₄ -haloalkenyl"), 2 to 6 ("C ₂ -C ₆ -haloalkenyl"), 2 to 8 ("C2-C6-haloalkenyl") or 2 to 10 ("C2-Cio-haloalkenyl") carbon atoms and a double bond in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like.

The term "alkynyl" as used herein refers to straight-chain or branched hydrocarbon groups having 2 to 3 ("C ₂ -C ₃ -alkynyl"), 2 to 4 ("C ₂ -C ₄ -alkynyl"), 2 to 6 ("C ₂ -C ₆ -alkynyl"), 2 to 8 ("C ₂ -C8-alkynyl"), or 2 to 10 ("C ₂ -Cio-alkynyl") carbon atoms and one or two triple bonds in any position, for example C ₂ -C3-alkynyl, such as ethynyl, 1 -propynyl or 2- propynyl; C ₂ -C ₄ -alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl and the like, C ₂ -C6-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl, 1 -pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1 -methyl-2-butynyl, 1 -methyl-3-butynyl, 2-methyl-3-butynyl, 3- methyl-1 -butynyl, 1 ,1 -dimethyl-2-propynyl, 1 -ethyl-2-propynyl, 1 -hexynyl, 2-hexynyl, 3- hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl-2-pentynyl, 1 -methyl-3-pentynyl, 1 -methyl-4- pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1 -pentynyl, 3-methyl-4- pentynyl, 4-methyl-1 -pentynyl, 4-methyl-2-pentynyl, 1 ,1 -dimethyl-2-butynyl, 1 ,1 - dimethyl-3-butynyl, 1 ,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1 - butynyl, 1 -ethyl-2-butynyl, 1 -ethyl-3-butynyl, 2-ethyl-3-butynyl, 1 -ethyl-1 -methyl-2- propynyl and the like; The term "haloalkynyl" as used herein, which is also expressed as "alkynyl which is partially or fully halogenated", refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 ("C ₂ -C ₄ -haloalkynyl"), 3 to 4 ("C ₃ -C ₄ -haloalkynyl"), 2 to 6 ("C ₂ -C ₆ -haloalkynyl"), 2 to 8 ("C ₂ -C ₈ -haloalkynyl") or 2 to 10 ("C ₂ -Cio-haloalkynyl") carbon atoms and one or two triple bonds in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine;

The term "cycloalkyl" as used herein refers to mono- or bi- or polycyclic saturated hydrocarbon radicals having 3 to 8 ("Cs-Cs-cycloalkyl"), in particular 3 to 6 carbon atoms ("C3-C6-cycloalkyl"). Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of monocyclic radicals having 3 to 8 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.2.1 ]heptyl, bicyclo[3.1 .1]heptyl, bicyclo[2.2.2]octyl and bicy- clo[3.2.1 ]octyl. Preferably, the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical.

The term "halocydoalkyl" as used herein, which is also expressed as "cycloalkyl which is partially or fully halogenated", refers to mono- or bi- or polycyclic saturated hydrocarbon groups having 3 to 8 ("Cs-Cs-halocycloalkyl" ) or preferably 3 to 6 ("C3-C6- halocycloalkyl") carbon ring members (as mentioned above) in which some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.

The term "cycloalkyl-Ci-C4-alkyl" refers to a Cs-Cs-cycloalkyl group ("Cs-Cs-cycloalkyl- Ci-C4-alkyl"), preferably a C3-C6-cycloalkyl group ("C3-C6-cycloalkyl-Ci-C4-alkyl"), more preferably a C3-C4-cycloalkyl group ("C3-C4-cycloalkyl-Ci-C4-alkyl") as defined above (preferably a monocyclic cycloalkyl group) which is bound to the remainder of the mol- ecule via a Ci-C4-alkyl group, as defined above. Examples for C3-C4-cycloalkyl-Ci-C4- alkyl are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutyl methyl, cy- clobutylethyl and cyclobutylpropyl, Examples for C3-C6-cycloalkyl-Ci-C4-alkyl, apart those mentioned for C3-C4-cycloalkyl-Ci-C4-alkyl, are cyclopentylmethyl, cyclopen- tylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl. Examples for C3-C8-cycloalkyl-Ci-C4-alkyl, apart those mentioned for C3-C6-cycloalkyl- Ci-C4-alkyl, are cycloheptylmethyl, cycloheptylethyl, cyclooctylmethyl and the like.

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

The term "Ci-C2-alkoxy" is a Ci-C2-alkyl group, as defined above, attached via an oxygen atom. The term "Ci-C3-alkoxy" is a Ci-C3-alkyl group, as defined above, attached via an oxygen atom. The term "Ci-C4-alkoxy" is a Ci-C4-alkyl group, as defined above, attached via an oxygen atom. The term "Ci-C6-alkoxy" is a Ci-C6-alkyl group, as defined above, attached via an oxygen atom. The term "Ci-Cio-alkoxy" is a Ci-Cio-alkyl group, as defined above, attached via an oxygen atom. Ci-C2-Alkoxy is methoxy or ethoxy. Ci-C3-Alkoxy is additionally, for example, n-propoxy and 1 -methylethoxy (iso- propoxy). Ci-C4-Alkoxy is additionally, for example, butoxy, 1 -methylpropoxy (sec- butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1 -dimethylethoxy (tert-butoxy). Ci-C6-Alkoxy is additionally, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethyl propoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 - dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3- dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2- trimethylpropoxy, 1 ,2,2-trimethylpropoxy, 1 -ethyl-1-methylpropoxy or 1 -ethyl-2- methylpropoxy. Ci-Cs-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2- ethylhexyloxy and positional isomers thereof. Ci-Cio-Alkoxy is additionally, for example, nonyloxy, decyloxy and positional isomers thereof.

The term "Ci-C2-haloalkoxy" is a Ci-C2-haloalkyl group, as defined above, attached via an oxygen atom. The term "Ci-C3-haloalkoxy" is a Ci-C3-haloalkyl group, as defined above, attached via an oxygen atom. The term "Ci-C4-haloalkoxy" is a Ci-C4-haloalkyl group, as defined above, attached via an oxygen atom. The term "Ci-C6-haloalkoxy" is a Ci-C6-haloalkyl group, as defined above, attached via an oxygen atom. The term "Ci- Cio-haloalkoxy" is a Ci-Cio-haloalkyl group, as defined above, attached via an oxygen atom. Ci-C ₂ -Haloalkoxy is, for example, OCH ₂ F, OCHF ₂ , OCF ₃ , OCH ₂ CI, OCHCI ₂ , OCC , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2- fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2- trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2- fluoroethoxy, 2,2,2-trichloroethoxy or OC ₂ F ₅ . Ci-C3-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy,

3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH ₂ -C ₂ F ₅ , OCF ₂ -

C ₂ F ₅ , 1 -(CH ₂ F)-2-fluoroethoxy, 1 -(CH ₂ CI)-2-chloroethoxy or 1 -(CH ₂ Br)-2-bromoethoxy. Ci-C4-Haloalkoxy is additionally, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4- bromobutoxy or nonafluorobutoxy. Ci-C6-Haloalkoxy is additionally, for example, 5- fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.

The term "Ci-C4-alkoxy-Ci-C4-alkyl" as used herein, refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above. The term "C1-C6- alkoxy-Ci-C6-alkyl" as used herein, refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above. Examples are methoxymethyl, ethoxyme- thyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobu- toxymethyl, tert-butoxymethyl, 1 -methoxyethyl, 1 -ethoxyethyl, 1 -propoxyethyl, 1 - isopropoxyethyl, 1 -n-butoxyethyl, 1 -sec-butoxyethyl, 1 -isobutoxyethyl, 1 -tert- butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n- butoxyethyl, 2-sec-butoxyethyl, 2-isobutoxyethyl, 2-tert-butoxyethyl, 1 -methoxypropyl, 1 -ethoxypropyl, 1 -propoxypropyl, 1 -isopropoxypropyl, 1 -n-butoxypropyl, 1 -sec- butoxypropyl, 1 -isobutoxypropyl, 1 -tert-butoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-isopropoxypropyl, 2-n-butoxypropyl, 2-sec-butoxypropyl, 2- isobutoxypropyl, 2-tert-butoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3- propoxypropyl, 3-isopropoxypropyl, 3-n-butoxypropyl, 3-sec-butoxypropyl, 3- isobutoxypropyl, 3-tert-butoxypropyl and the like.

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

Ci-C6-Haloalkoxy-Ci-C6-alkyl is a straight-chain or branched alkyl group having from 1 to 6, especially 1 to 4 carbon atoms (=Ci-C6-haloalkoxy-Ci-C4-alkyl), wherein one of the hydrogen atoms is replaced by a Ci-C6-alkoxy group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remaining hydrogen atoms (either in the alkoxy moiety or in the alkyl moiety or in both) are replaced by halogen atoms. Ci-C4-Haloalkoxy-Ci-C4-alkyl is a straight-chain or branched alkyl group having from 1 to 4 carbon atoms, wherein one of the hydrogen atoms is replaced by a Ci-C4-alkoxy group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remaining hydrogen atoms (either in the alkoxy moiety or in the alkyl moiety or in both) are replaced by halogen atoms. Examples are difluoro- methoxymethyl (CHF2OCH2), trifluoromethoxymethyl, 1 -difluoromethoxyethyl , 1 - trifluoromethoxyethyl, 2-difluoromethoxyethyl, 2-trifluoromethoxyethyl, difluoro- methoxy-methyl (CH3OCF2), 1 ,1 -difluoro-2-methoxyethyl, 2,2-difluoro-2-methoxyethyl and the like.

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

2-methylbutylthio, 3-methylbutylthio, 1 ,1 -dimethylpropylthio, 1 ,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 1 -methylpentylthio, 2- methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1 ,1 -dimethylbutylthio, 1 ,2- dimethylbutylthio, 1 ,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1 -ethylbutylthio, 2-ethylbutylthio, 1 ,1 ,2-trimethylpropylthio, 1 ,2,2- trimethylpropylthio, 1 -ethyl-1 -methylpropylthio or 1-ethyl-2-methylpropylthio. Ci-Cs- Alkylthio is additionally, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof. Ci-Cio-Alkylthio is additionally, for example, nonylthio, decylthio and positional isomers thereof.

The term "Ci-C2-haloalkylthio" is a Ci-C2-haloalkyl group, as defined above, attached via a sulfur atom. The term "Ci-C3-haloalkylthio" is a Ci-C3-haloalkyl group, as defined above, attached via a sulfur atom. The term "Ci-C4-haloalkylthio" is a Ci-C4-haloalkyl group, as defined above, attached via a sulfur atom. The term "Ci-C6-haloalkylthio" is a Ci-C6-haloalkyl group, as defined above, attached via a sulfur atom. The term "C1-C10- haloalkylthio" is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfur atom. Ci-C ₂ -Haloalkylthio is, for example, SCH ₂ F, SCHF ₂ , SCF ₃ , SCH ₂ CI, SCHC , SCCI ₃ , chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2- fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2- difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2- difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio or SC2F5. C1-C3- Haloalkylthio is additionally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2- difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3- dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio,

3,3,3-trichloropropylthio, SCH2-C2F5, SCF2-C2F5, 1-(CH ₂ F)-2-fluoroethylthio, 1 -(CH ₂ CI)- 2-chloroethylthio or 1 -(CH2Br)-2-bromoethylthio. Ci-C4-Haloalkylthio is additionally, for example, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio. Ci-C6-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6- chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio.

The term "C 1 -C2-a I ky Is u If i nyl" is a Ci-C2-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-C4-alkylsulfinyl" is a Ci-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-C6-alkylsulfinyl" is a C1-C6- alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "C1-C10- alkylsulfinyl" is a Ci-Cio-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. Ci-C2-Alkylsulfinyl is methylsulfinyl or ethylsulfinyl. C 1 -C4- Al ky I s u If i nyl is additionally, for example, n-propylsulfinyl, 1 -methylethylsulfinyl (isopropylsulfinyl), butyl- sulfinyl, 1 -methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfi- nyl) or 1 ,1 -dimethylethylsulfinyl (tert-butylsulfinyl). Ci-C6-Alkylsulfinyl is additionally, for example, pentylsulfinyl, 1 -methylbutylsulfinyl, 2-methylbutylsulfinyl, 3- methylbutylsulfinyl, 1 ,1 -dimethylpropylsulfinyl, 1 ,2-dimethylpropylsulfinyl,

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

1 -ethylbutylsulf inyl , 2-ethylbutylsulfinyl, 1 ,1 ,2-trimethylpropylsulfinyl, 1 ,2,2- trimethylpropylsulfinyl, 1 -ethyl-1 -methylpropylsulfinyl or 1 -ethyl-2-methylpropylsulfinyl. Ci-Ce-Alkylsulfinyl is additionally, for example, heptylsulfinyl, octylsulfinyl, 2- ethylhexylsulfinyl and positional isomers thereof. Ci-Cio-Alkylsulfinyl is additionally, for example, nonylsulfinyl, decylsulfinyl and positional isomers thereof. The term "Ci-C2-haloalkylsulfinyl" is a Ci-C2-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-C4-haloalkylsulfinyl" is a Ci-C4-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "C1-C6- haloalkylsulfinyl" is a Ci-C6-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-Cio-haloalkylsulfinyl" is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group. Ci-C2-Haloalkylsulfinyl is, for example, S(0)CH ₂ F, S(0)CHF ₂ , S(0)CF ₃ , S(0)CH ₂ CI, S(0)CHCI ₂ , S(0)CCI ₃ , chlorofluorome- thylsulfinyl, dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl, 2- fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2- difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro- 2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl or S(0)C2F ₅ . Ci-C4-Haloalkylsulfinyl is additionally, for example, 2-fluoropropylsulfinyl, 3- fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl,

2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2,3-dichloropropylsulfinyl, 2- bromopropylsulfinyl, 3-bromopropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3- trichloropropylsulfinyl, S(0)CH ₂ -C ₂ F ₅ , S(0)CF ₂ -C ₂ F ₅ , 1 -(CH ₂ F)-2-fluoroethylsulfinyl, 1 - (CH ₂ CI)-2-chloroethylsulfinyl, 1 -(CH ₂ Br)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl, 4- chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorobutylsulfinyl. C1-C6- Haloalkylsulfinyl is additionally, for example, 5-fluoropentylsulfinyl, 5- chloropentylsulfinyl, 5-brompentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfi- nyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl.

The term "Ci-C2-alkylsulfonyl" is a Ci-C2-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci-C3-alkylsulfonyl" is a Ci-C3-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci-C4-alkylsulfonyl" is a C1-C4- alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "C1-C6- alkylsulfonyl" is a Ci-C6-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci-Cio-alkylsulfonyl" is a Ci-Cio-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. Ci-C2-Alkylsulfonyl is methylsulfonyl or ethyl- sulfonyl. Ci-C3-Alkylsulfonyl is additionally, for example, n-propylsulfonyl or 1 - methylethylsulfonyl (isopropylsulfonyl). Ci-C4-Alkylsulfonyl is additionally, for example, butylsulfonyl, 1 -methylpropylsulfonyl (sec-butylsulfonyl), 2-methylpropylsulfonyl (isobu- tylsulfonyl) or 1 ,1 -dimethylethylsulfonyl (tert-butylsulfonyl). Ci-C6-Alkylsulfonyl is addi- tionally, for example, pentylsulfonyl, 1 -methylbutylsulfonyl, 2-methylbutylsulfonyl, 3- methylbutylsulfonyl, 1 ,1 -dimethylpropylsulfonyl, 1 ,2-dimethylpropylsulfonyl,

2,2-dimethylpropylsulfonyl, 1 -ethylpropylsulfonyl, hexylsulfonyl, 1 -methylpentylsulfonyl,

2- methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1 ,1 - dimethylbutylsulfonyl, 1 ,2-dimethylbutylsulfonyl, 1 ,3-dimethylbutylsulfonyl, 2,2- dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl,

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

The term "Ci-C2-haloalkylsulfonyl" is a Ci-C2-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci-C3-haloalkylsulfonyl" is a C1-C3- haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci- C4-haloalkylsulfonyl" is a Ci-C4-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci-C6-haloalkylsulfonyl" is a Ci-C6-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "C1-C10- haloalkylsulfonyl" is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfonyl [S(0) ₂ ] group. Ci-C ₂ -Haloalkylsulfonyl is, for example, S(0) ₂ CH ₂ F, S(0) ₂ CHF ₂ , S(0) ₂ CF ₃ , S(0) ₂ CH ₂ CI, S(0) ₂ CHCI ₂ , S(0) ₂ CCI ₃ , chlorofluoromethylsulfonyl, dichloro- fluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2- chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2- difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl or S(0)2C2F ₅ . Ci-C3-Haloalkylsulfonyl is additionally, for example, 2-fluoropropylsulfonyl,

3- fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,

2- chloropropylsulfonyl, 3-chloropropylsulfonyl, 2,3-dichloropropylsulfonyl, 2- bromopropylsulfonyl, 3-bromopropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3- trichloropropylsulfonyl, S(0) ₂ CH2-C2F ₅ , S(0)2CF2-C ₂ F ₅ , 1 -(CH ₂ F)-2-fluoroethylsulfonyl, 1 -(CH ₂ CI)-2-chloroethylsulfonylor 1 -(CH ₂ Br)-2-bromoethylsulfonyl. C1-C4- Haloalkylsulfonyl is additionally, for example, 4-fluorobutylsulfonyl, 4- chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl. C1-C6- Haloalkylsulfonyl is additionally, for example, 5-fluoropentylsulfonyl, 5- chloropentylsulfonyl, 5-brompentylsulfonyl, 5-iodopentylsulfonyl, undecafluoropen- tylsulfonyl, 6-fluorohexylsulfonyl, 6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6- iodohexylsulfonyl or dodecafluorohexylsulfonyl.

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

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

The term "haloalkylcarbonyl" is a Ci-C6-haloalkyl ("Ci-C6-haloalkylcarbonyl"), preferably a Ci-C4-haloalkyl ("Ci-C4-haloalkylcarbonyl") group, as defined above, attached via a carbonyl [C(=0)] group. Examples are trifluoromethylcarbonyl, 2,2,2- trifluoroethylcarbonyl and the like.

The term "alkoxycarbonyl" is a Ci-C6-alkoxy ("Ci-C6-alkoxycarbonyl"), preferably a Ci- C4-alkoxy ("Ci-C4-alkoxycarbonyl") group, as defined above, attached via a carbonyl [C(=0)] group. Examples are methoxycarbonyl), ethoxycarbonyl, propoxycarbonyl, iso- propoxycarbonyl, n-butoxycarbonyl and the like.

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

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

The term "di-(Ci-C6-alkyl)amino" is a group -N(Ci-C6-alkyl)2. Examples are dimethyla- mino, diethylamino, ethylmethylamino, dipropylamino, diisopropylamino, methylpropyl- amino, methylisopropylamino, ethylpropylamino, ethylisopropylamino, dibutylamino and the like.

The term "3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or het- eroatom groups selected from N, O, S, NO, SO and SO2, as ring members" denotes a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximum unsaturated heteromonocyclic ring or a 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members.

Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond(s). Maximally unsaturated rings contain as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the ring size. Maximally unsaturated 5- or 6-membered heterocyclic rings are aromatic. The heterocyclic ring may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. As a matter of course, the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.

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

Examples of a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring include: Oxira- nyl, thiiranyl, aziridinyl, oxetanyl, thietanyl, azetidinyl, tetrahydrofuran-2-yl, tetrahydrofu- ran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1 -yl, pyrrolidin-2-yl, pyrrol- idin-3-yl, pyrazolidin-1 -yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazoli- din-1 -yl, imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl, oxazolidin- 4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxazolidin-3-yl, isoxazolidin-4-yl, isoxazolidin-5- yl, thiazolidin-2-yl, thiazolidin-3-yl, thiazolidin-4-yl, thiazolidin-5-yl, isothiazolidin-2-yl, isothiazolidin-3-yl, isothiazolidin-4-yl, isothiazolidin-5-yl, 1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4- oxadiazolidin-5-yl, 1 ,2,4-thiadiazolidin-3-yl, 1 ,2,4-thiadiazolidin-5-yl, 1 ,2,4-triazolidin-3- yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4-thiadiazolidin-2-yl, 1 ,3,4-triazolidin-1 -yl, 1 ,3,4- triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 1 ,3-dioxan-5-yl, 1 ,4-dioxan-2- yl, piperidin-1 -yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahy- dropyrimidin-5-yl, piperazin-1 -yl, piperazin-2-yl, 1 ,3,5-hexahydrotriazin-1 -yl,

1 ,3,5-hexahydrotriazin-2-yl and 1 ,2,4-hexahydrotriazin-3-yl, morpholin-2-yl, morpholin- 3-yl, morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl, thiomorpholin-4-yl, 1 - oxothiomorpholin-2-yl, 1 -oxothiomorpholin-3-yl, 1 -oxothiomorpholin-4-yl, 1 ,1 - dioxothiomorpholin-2-yl, 1 ,1 -dioxothiomorpholin-3-yl, 1 ,1 -dioxothiomorpholin-4-yl, aze- pan-1 -, -2-, -3- or -4-yl, oxepan-2-, -3-, -4- or -5-yl, hexahydro-1 ,3-diazepinyl, hexahy- dro-1 ,4-diazepinyl, hexahydro-1 ,3-oxazepinyl, hexahydro-1 ,4-oxazepinyl, hexahydro- 1 ,3-dioxepinyl, hexahydro-1 ,4-dioxepinyl and the like.

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

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

2- isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-

3- yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl,

2- isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,

2.3- dihydropyrazol-5-yl, 3,4-dihydropyrazol-1 -yl, 3,4-dihydropyrazol-3-yl,

3.4- dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1 -yl,

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

2.3- d i hyd rooxazol-2-yl , 2 , 3-d i hyd rooxazol-3-yl , 2 , 3-d i hyd rooxazol-4-yl ,

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

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

3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridi- nyl, 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropy- rimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydro- pyrazinyl, 1 ,3, 5-di- or tetrahydrotriazin-2-yl, 1 ,2, 4-di- or tetrahydrotriazin-3-yl, 2,3,4,5- tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-, -

3- , -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydrooxepinyl, such as 2,3,4,5-tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7- tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1 H]oxepin-2-, -3-, -

4- , -5-, -6- or -7-yl, tetrahydro-1 ,3-diazepinyl, tetrahydro-1 ,4-diazepinyl, tetrahydro-1 ,3- oxazepinyl, tetrahydro-1 ,4-oxazepinyl, tetrahydro-1 ,3-dioxepinyl and tetrahydro-1 ,4- dioxepinyl.

Examples for a 3-, 4-, 5-, 6- or 7-membered maximally unsaturated (including aromatic) heterocyclic ring are 5- or 6-membered heteroaromatic rings, such as 2-furyl, 3-furyl, 2- thienyl, 3-thienyl, 1 -pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl,

5- pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1 - imidazolyl, 2-imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-1 -yl, 1 ,3,4-triazol-2-yl, 2-pyridinyl, 3- pyridinyl, 4-pyridinyl, 1 -oxopyridin-2-yl, 1 -oxopyridin-3-yl, 1 -oxopyridin-4-yl,3- pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl, and also homoaromatic radicals, such as 1 H-azepine, 1 H-[1 ,3]-diazepine and 1 H-[1 ,4]- diazepine.

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

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

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

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

A saturated 3-, 4-, 5-, 6-, 7-, 8- or 9-membered ring, wherein the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from O, S, N, NR ¹⁴ , NO, SO and SO2 and/or 1 or 2 groups selected from C=0, C=S and C=NR ¹⁴ as ring members is either carbocyclic or heterocyclic. Examples are, in addition to the saturated heteromonocy- clic rings mentioned above, carbocyclic rings, such as cyclopropyl, cyclopropanonyl, cyclobutyl, cyclobutanonyl, cyclopentyl, cyclopentanonyl, cyclohexyl, cyclohexanonyl, cyclohexadienonyl, cycloheptyl, cycloheptanonyl, cyclooctyl, cyclooctanonyl, furan-2- onyl, pyrrolidine-2-onyl, pyrrolidine-2,5-dionyl, piperidine-2-only, piperidine-2,6-dionyl and the like.

The remarks made below concerning preferred embodiments of the variables of the compounds of formula I, especially with respect to their substituents A, A ¹ , A ² , A ³ , A ⁴ , B , B ² , B ³ , G ¹ , G ² , G ³ , G ⁴ , R ¹ , R ² , R ^3a , R ^3b , R ^3c , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ^10a , R ^10b , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ^14a , R ^14b , R ¹⁵ , R ¹⁶ , m and n, the features of the use and method according to the invention and of the composition of the invention are valid both on their own and, in particular, in every possible combination with each other.

In one embodiment of the invention, A is A ¹ .

In one preferred embodiment, A ¹ is selected from -C(=NR ⁶ )R ⁸ and -N(R ⁵ )R ⁶ and is more preferably -C(=NR ⁶ )R ⁸ ; wherein R ⁵ , R ⁶ and R ⁸ have one of the above general meanings, or, in particular, one of the below preferred meanings.

R ⁶ as a radical in the group -C(=NR ⁶ )R ⁸ is preferably selected from hydrogen, cyano, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last- mentioned aliphatic and cycloaliphatic radicals each independently may be partially or fully halogenated and/or may be substituted with 1 , 2, 3, 4, 5 or 6, preferably 1 , 2 or 3, in particular 1 , substituents R ⁸ ; OR ⁹ and NR ^10a R ^10b ; wherein R ⁸ , R ⁹ , R ^10a and R ^10b have one of the above general meanings, or, in particular, one of the below preferred meanings.

More preferably, R ⁶ in -C(=NR ⁶ )R ⁸ is selected from hydrogen, Ci-Cio-alkyl, C3-C8- cycloalkyl, wherein the two last-mentioned aliphatic and cycloaliphatic radicals each independently may be partially or fully halogenated and/or may be substituted with 1 , 2 or 3, preferably 1 or 2, in particular 1 , substituents R ⁸ ; OR ⁹ and NR ^10a R ^10b ; wherein R ⁸ , R ⁹ , R ^10a and R ^10b have one of the above general meanings, or, in particular, one of the below preferred meanings.

Even more preferably, R ⁶ in -C(=NR ⁶ )R ⁸ is selected from OR ⁹ and NR ^10a R ^10b ; wherein R ⁸ , R ⁹ , R ^10a and R ^10b have one of the above general meanings, or, in particular, one of the below preferred meanings. In OR ⁹ as a preferred meaning of R ⁶ in -C(=NR ⁶ )R ⁸ , R ⁹ is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-C8- cycloalkyl-Ci-C4-alkyl-, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6- haloalkynyl, and more preferably from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl and C3-C8-cycloalkyl-Ci-C4-alkyk

In NR ^10a R ^10b as a preferred meaning of R ⁶ in -C(=NR ⁶ )R ⁸ , R ^10a and R ^10b , independently of each other, are selected from the group consisting of hydrogen, Ci-C6-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl,

-C(=0)OR ¹⁵ , -C(=0)N(R ^4a )R ⁴ , -C(=S)N(R ^4a )R ⁴ , phenyl which is optionally substituted with 1 , 2, 3 or 4, substituents R ¹⁶ , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more sub- stituents R ¹⁶ ;

or R ^10a and R ^10b form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl; wherein R ^14a , R ^14b and R ¹⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings.

More preferably,

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

R ^10b is selected from Ci-C ₆ -alkyl, Ci-C ₆ -haloalkyl, d-Ce-alkylcarbonyl, Ci-C ₆ - haloalkylcarbonyl, -C(=0)OR ¹⁵ , -C(=0)N(R ^4a )R ^4b , -C(=S)N(R ^4a )R ^4b , phenyl which is optionally substituted with 1 , 2, 3 or 4, substituents R ¹⁶ , and a 5- or 6- membered heteroaromatic ring comprising 1 , 2 or 3 heteroatoms selected from N, O and S, as ring members, where the heteroaromatic ring is optionally substituted with one or more substituents R ¹⁶ ;

wherein R ^14a , R ^14b and R ¹⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings.

In the above radicals R ^10a and R ^10b ,

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

R ^14b is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl-, Ci-C6-alkyl substituted with a CN group, Ci-C6-alkoxyl, Ci-C6-haloalkoxy, phenyl which is optionally substituted with 1 , 2, 3 or 4, substituents each independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4- haloalkynyl; and a heterocyclic ring selected from rings of formulae E-1 to E-51 defined below.

In an alternatively preferred embodiment, R ^10a and R ^10b , independently of each other, are selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl,

-C(=0)N(R ^14a )R ¹⁴ , -C(=S)N(R ^14a )R ¹⁴ , phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ , and a 3-, 4-, 5-, 6- or 7- membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ ;

or R ^10a and R ^10b form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocy- die ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more, preferably 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl; wherein R ^14a , R ^14b and R ¹⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings.

In an alternatively more preferred embodiment,,

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

R ^10b is selected from -C(=0)N(R ^14a )R ^14b , -C(=S)N(R ^14a ) R ^14b , phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ , and a 5- or 6-membered heteroaromatic ring comprising 1 , 2 or 3 heteroatoms selected from N , O and S, as ring members, where the heteroaromatic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ ;

wherein R ^14a , R ^14b and R ¹⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings.

In the above radicals R ^10a and R ^10b of the above alternatively preferred and more preferred embodiments,

R ^14a is preferably selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl; and R ^14b is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkenyl, Ci-C6-haloalkenyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-Ci-C4- alkyl-, Ci-C6-alkyl substituted with a CN group, phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ , which are each independently preferably selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; and a heterocyclic ring selected from rings of following formulae E-1 to E-51 :

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

E-6 E-7 E-9

E-10 E-11 E-12 E-13 E-14

E-51 wherein

k is 0, 1 , 2 or 3, n is 0, 1 or 2,

n is 0, 1 or 2; and

each R ¹⁶ is independently selected from the group consisting of halogen, cy- ano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci- C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2- C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or two R ¹⁶ present on the same carbon atom of a saturated ring may form to- gether a group =0 or =S.

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

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

R ^14b is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-methyl-, Ci- C6-alkyl substituted with a CN group, phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4- haloalkynyl; and a 4-membered saturated heterocyclic ring comprising one heteroatom or heteroatom group selected from S, SO and SO2 as ring member (ring E-44), where the heterocyclic ring is optionally substituted with one or more, preferably 1 or 2, in particular 1 , substituents R ¹⁶ ;

wherein each R ¹⁶ is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or

two R ¹⁶ present on the same carbon atom may form together a group =0 or =S..

Preferably, in the above radicals, each R ¹⁶ is independently selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

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

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

R ^14b is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and C3-C6-cycloalkyl- methyl-. R ⁸ as a radical in the group -C(=NR ⁶ )R ⁸ is preferably selected from hydrogen, C1-C4- alkyl, Ci-C4-haloalkyl and NR ^10a R ^10b , and more preferably from hydrogen and

NR ^10a R ^10b , and is specifically hydrogen. In this case (i.e. in NR ^10a R ^10b as a meaning of R ⁸ ), R ^10a and R ^10b are preferably selected, independently of each other, from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C4-haloalkylaminocarbonyl, C3-C6-cycloalkylaminocarbonyl and C3-C6- halocycloalkylaminocarbonyl,

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

More preferably, R ^10a and R ^10b are in this case selected, independently of each other, from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci- C4-alkylaminocarbonyl and Ci-C4-haloalkylaminocarbonyl.

In an alternative embodiment of the invention, A is A ² . In A ² , W is preferably O.

In A ² , Y is preferably N(R ⁵ )R ⁶ ; wherein R ⁵ and R ⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings. In an alternatively preferred embodiment, in A ² Y is hydrogen.

In an alternatively preferred embodiment, in A ² Y is -OR ⁹ . R ⁹ has one of the above general meanings, or, in particular, is selected from hydrogen, Ci-C6-alkyl, C1-C6- haloalkyl and Ci-C6-alkyl substituted by one radical R ¹³ , where R ¹³ has one of the above general meanings, or, in particular, one of the below preferred meanings.

More preferably, in A ² , W is O and Y is N(R ⁵ )R ⁶ ; wherein R ⁵ and R ⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings. In alternatively more preferred embodiment, in A ² , W is O and Y H.

In alternatively more preferred embodiment, in A ² , W is O and Y is -OR ⁹ , where R ⁹ has one of the above general meanings, or, in particular, is selected from hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl and Ci-C6-alkyl substituted by one radical R ¹³ , where R ¹³ has one of the above general meanings, or, in particular, one of the below preferred meanings.

In N (R ⁵ )R ⁶ as a radical Y,

R ⁵ is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl and C3-C8- halocycloalkyl, where the aforementioned aliphatic and cycloaliphatic radicals may be substituted by 1 , 2 or 3, preferably 1 , radicals R ⁸ ; and

R ⁶ is preferably selected from hydrogen, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-C10- alkenyl, C2-Cio-alkynyl, wherein the four last-mentioned aliphatic and cycloali- phatic radicals may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ⁸ ,

OR ⁹ , N R ^10a R ^10b , S(0) _n R ⁹ , C(=O)N R ^0a N(R ^0a R ^0b ), C(=0)R ⁸ ,

phenyl which may be substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular 1 , substituents R ^{1 1} , and

a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N , O, S, NO, SO and SO2, as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substit- uents R ^{1 1} ;

or

R ⁵ and R ⁶ , together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, where the ring may further contain 1 , 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, SO, SO2, N , N H , C=0 and

C=S as ring members, wherein the heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, wherein the aliphatic or cycloaliphatic moieties in the twelve last- mentioned radicals may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ⁸ , and phenyl which may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R ¹¹ ; or

R ⁵ and R ⁶ together form a group =C(R ⁸ ) ₂ , =S(0) _m (R ⁹ ) ₂ , =NR ^10a or =NOR ⁹ ;

wherein R ⁸ , R ⁹ , R ^10a , R ^10b and R ¹¹ have one of the above general meanings, or, in particular, one of the below preferred meanings.

More preferably, in N(R ⁵ )R ⁶ as a radical Y,

R ⁵ is selected from hydrogen, Ci-C6-alkyl, C2-C3-alkynyl and -Chb-CN; and

R ⁶ is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C10- haloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, where the four last-mentioned aliphatic and cycloaliphatic radicals may carry 1 , 2 or 3 radicals

R ⁸ ; d-Ce-alkoxy, Ci-C ₆ -haloalkoxy, N(R ^10a )R ^10b , phenyl which may be substituted with 1 , 2, 3, 4, or 5 substituents R ¹¹ , and a 3-,

4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic ring may be substituted with one or more substituents R ¹¹ ; wherein R ⁸ and R ¹¹ are as defined in claim 1 ;

or

R ⁵ and R ⁶ , together with the nitrogen atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated heterocyclic ring, where the ring may further contain

1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, SO, SO2, NH and C=0 as ring members, wherein the heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and C1-C6- haloalkoxy;

or

R ⁵ and R ⁶ , together with the nitrogen atom to which they are bound, form a group where R ⁹ is selected from Ci-C6-alkyl and Ci-C6-haloalkyl. Even more preferably, in N(R ⁵ )R ⁶ as a radical Y,

R ⁵ is selected from hydrogen, Ci-C6-alkyl, C2-C3-alkynyl and CH2-CN; and

R ⁶ is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl which carries one radical R ⁸ , C2-C6-alkenyl, C2-Cio-haloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl which may be substituted by 1 or 2 substituents selected from F, CN and pyridyl;

Ci-Ce-alkoxy, Ci-C ₆ -haloalkoxy, N(R ^0a )R ^0b ,

phenyl which may be substituted with 1 , 2, 3, 4, or 5 substituents R ¹¹ , and a 3-, 4- , 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups in- dependently selected from N , O, S, NO, SO and SO2, as ring members, where the heteromonocyclic ring may be substituted with one or more substituents R ^{1 1} ; wherein R ⁸ and R ^{1 1} are as defined in claim 1 ;

or

R ⁵ and R ⁶ , together with the nitrogen atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated heterocyclic ring, where the ring may further contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, SO, SO2, N H and C=0 as ring members, wherein the heterocyclic ring may be substituted with 1 , 2 or 3 substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and C1-C6- haloalkoxy;

or

R ⁵ and R ⁶ , together with the nitrogen atom to which they are bound, form a group where R ⁹ is selected from Ci-C6-alkyl and Ci-C6-haloalkyl.

Particularly preferably, in N(R ⁵ )R ⁶ as a radical Y,

R ⁵ selected from hydrogen, Ci-C6-alkyl, C2-C3-alkynyl and CH2-CN ; and

R ⁶ is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl which carries one radical R ⁸ , C2-C6-alkenyl, C2-Cio-haloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl which may be substituted by 1 or 2 substituents selected from F, CN and pyridyl;

d-Ce-alkoxy, Ci-C ₆ -haloalkoxy, N(R ^10a )R ^10b , wherein R ^10a is selected from hydrogen and Ci-C6-alkyl and R ^10b is selected from a 5- or 6-membered het- eroaromatic ring containing 1 , 2 or 3 heteroatoms selected from N , O and S as ring members, where the heteroaromatic ring may be substituted with one or more substituents R ¹⁶ ;

phenyl which may be substituted with 1 , 2, 3, 4, or 5 substituents R ^{1 1} , and a 3-, 4- , 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups independently selected from N , O, S, NO, SO and SO2, as ring members, where the heteromonocyclic ring may be substituted with one or more substituents R ^{1 1} ; wherein

each R ^{1 1} is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci- C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2- C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or two R ^{1 1} present on the same carbon atom of a saturated heterocyclic ring may form together =0 or =S;

R ⁸ is selected from OH , CN , Cs-Cs-cycloalkyl which optionally carries a CN substituent, Cs-Cs-halocycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, - C(=O)N(R ^10a )R ^10b , phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substitu- ents R ¹⁶ , and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2 or 3 heteroa- toms or heteroatom groups independently selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic ring may be substituted with one or more substituents R ¹⁶ ;

wherein

R ^10a is selected from the group consisting of hydrogen and Ci-C6-alkyl;

R ^10b is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C4- alkynyl, CH ₂ -CN, Ci-C ₆ -haloalkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ - halocycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, and

each R ¹⁶ as a substituent on phenyl or the heterocyclic rings is independently selected from the group consisting of halogen, cyano, ni- tro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci- C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or

two R ¹⁶ present on the same carbon atom of a saturated heterocyclic ring may form together =0 or =S;

or

R ⁵ and R ⁶ , together with the nitrogen atom to which they are bound, form a 5- or 6- membered saturated heterocyclic ring, where the ring may further contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, SO, SO2, NH and C=0 as ring members, wherein the heterocyclic ring may be substituted with 1 , 2 or 3 substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy; or

R ⁵ and R ⁶ , together with the nitrogen atom to which they are bound, form a group where R ⁹ is selected from Ci-C6-alkyl and Ci-C6-haloalkyl.

Alternatively, more preferably, in N(R ⁵ )R ⁶ as a radical Y,

R ⁵ is selected from hydrogen, Ci-C6-alkyl, C2-C3-alkynyl, CH2-CN and Ci-C6-alkoxy- methyl-; and

R ⁶ is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, where the four last-mentioned aliphatic and cycloaliphatic radicals may carry 1 , 2 or 3, preferably 1 , radicals R ⁸ ; C(=0)R ⁸ , phenyl which may be substituted with 1 , 2, 3, 4, or 5 substituents R ¹¹ , and a 3-, 4-, 5-, 6- or 7- membered saturated, partially unsaturated or maximally unsaturated heteromon- ocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic ring may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹¹ ;

wherein R ⁸ and R ¹¹ have one of the above general meanings, or, in particular, one of the below preferred meanings;

or

R ⁵ and R ⁶ , together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated heterocyclic ring, where the ring may further contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, SO, SO2, NH and C=0, preferably from O, NH and C=0, as ring members, wherein the heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy.

Preferably, the 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring R ⁶ containing 1 , 2 or 3 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2, as ring members is selected from rings D-1 to D-173 listed below in context with A ⁴ . The ring may be sub- stituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹¹ .

Alternatively, particularly preferably, in N(R ⁵ )R ⁶ as a radical Y,

R ⁵ is selected from hydrogen, Ci-C6-alkyl, C2-C3-alkynyl, CH2-CN and Ci-C6-alkoxy- methyl-; and

R ⁶ is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl which may be substituted by 1 or 2 substituents selected from F, CN, methyl and oxo; Ci-C4-alkyl which carries one radical R ⁸ ; C(=0)R ⁸ , phenyl which may be substituted with 1 , 2, 3, 4, or 5 substituents R ¹¹ , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring con- taining 1 , 2 or 3 heteroatoms or heteroatom groups independently selected from

N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic ring may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹¹ ;

wherein R ⁸ and R ¹¹ have one of the above general meanings, or, in particular, one of the below preferred meanings;

or

R ⁵ and R ⁶ , together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated heterocyclic ring, where the ring may further contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, SO, SO2, NH and C=0, preferably from O, NH and C=0, as ring members, wherein the heterocyclic ring may be substituted with 1 , 2 or 3 substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy and Ci-C6-haloalkoxy.

Alternatively, even more preferably, in N(R ⁵ )R ⁶ as a radical Y,

R ⁵ is selected from hydrogen and Ci-C6-alkyl; and

R ⁶ is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl which carries one radical R ⁸ , C3-C6-cycloalkyl which may be substituted by 1 or 2 substituents selected from F, CN, methyl and oxo,

C(=0)R ⁸ , phenyl which may be substituted with 1 , 2, 3, 4, or 5 substituents R ¹¹ , and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic ring may be substituted with one or more substituents R ¹¹ ;

wherein R ⁸ and R ¹¹ have one of the above general meanings, or, in particular, one of the below preferred meanings;

or

R ⁵ and R ⁶ , together with the nitrogen atom to which they are bound, form a 5- or

6-membered saturated heterocyclic ring, where the ring may further contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, SO, SO2, NH and C=0, preferably from O, NH and C=0, as ring members, wherein the heterocyclic ring may be substituted with 1 , 2 or 3 substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy and Ci-C6-haloalkoxy.

Preferably the 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2, as ring members is selected from rings D-1 to D-173 listed below in context with A ⁴ , and more preferably from rings F-1 to F-51 listed below. The ring may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹¹ . In particular, in N(R ⁵ )R ⁶ as a radical Y,

R ⁵ is selected from hydrogen and methyl, preferably hydrogen; and

R ⁶ is selected from Ci-C4-alkyl which carries one radical R ⁸ , preferably methyl which carries one radical R ⁸ , Ci-C4-haloalkyl, and a 4-, 5- or 6-membered saturated heteromonocyclic ring containing 1 het- eroatom or heteroatom group selected from S, SO and SO2, as ring member, where the heteromonocyclic ring may be substituted with one or more substitu- ents R ¹¹ ;

wherein R ⁸ and R ¹¹ have one of the above general meanings, or, in particular, one of the below preferred meanings;

or

R ⁵ and R ⁶ , together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated heterocyclic ring (i.e. R ⁵ and R ⁶ form together -(Chb or - (CH2)5-), wherein the heterocyclic ring may be substituted with 1 , 2 or 3 substitu- ents independently selected from the group consisting of halogen, cyano, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy.

Preferably the 4-, 5- or 6-membered saturated heteromonocyclic ring containing 1 het- eroatom or heteroatom group selected from S, SO and SO2, as ring member is selected from rings D-72, D-77, D-78 and D-100 to D-102 listed below in context with A ⁴ . The ring may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substitu- ents R ¹¹ . More preference is given to ring D-72 with n = 0 (thietan-3-yl) and its oxidized analogs with n = 1 and n = 2 (1 -oxo-thietan-3-yl and 1 ,1 -dioxo-thietan-3-yl)

In N(R ⁵ )R ⁶ as a radical Y,

R ⁸ as a substituent on an aliphatic or cycloaliphatic group is preferably selected from cyano, Cs-Cs-cycloalkyl which may be substituted by 1 or 2 substituents selected from CN, methyl and oxo, C ₃ -C ₈ -halocycloalkyl, OR ⁹ , S(0) _n R ⁹ , N(R ^0a )R ^0b , C(=O)N(R ^0a )R ^0b , C(=0)OR ⁹ , phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ , and a 3-, 4-, 5-, 6- or 7- membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ ; and

R ⁸ in the group C(=0)R ⁸ is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OR ⁹ and N(R ^0a )R ^0b ;

wherein R ⁹ , R ^10a , R ^10b and R ¹⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings.

More preferably, in N(R ⁵ )R ⁶ as a radical Y,

R ⁸ as a substituent on an aliphatic or cycloaliphatic group is selected from Cs-Cs- cycloalkyl, Cs-Cs-halocycloalkyl, -C(=O)N(R ^0a )R ⁰ , -C(=S)N(R ^0a )R ⁰ , -C(=0)OR ⁹ , phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ ;

or

two R ⁸ present on the same carbon atom together form a group =0, =S; =S(0) _m (R ¹⁵ ) ₂ , =S(0) _m R ¹⁵ N(R ^4a )R ^4b , =NR ^0a , =NOR ⁹ ; or =NNR ^10a R ^10b ;

and

R ⁸ in the group C(=0)R ⁸ is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, OR ⁹ and N(R ^0a )R ^0b ;

wherein R ⁹ , R ^10a , R ^10b and R ¹⁶ have one of the above general meanings, or, in particular, one of the below preferred meanings.

Even more preferably, in N(R ⁵ )R ⁶ as a radical Y, R ⁸ as a substituent on an aliphatic or cycloaliphatic group is selected from -C(=O)N(R ^10a )R ^10b , phenyl and a 5- or 6- membered heteroaromatic ring comprising 1 , 2 or 3 heteroatoms selected from N, O and S, as ring members, where the heteroaromatic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ .

In this case,

R ^10a and R ^10b are preferably selected, independently of each other, from hydrogen, Ci- C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkylcarbonyl, C1-C4- haloalkylcarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C4-haloalkylaminocarbonyl, C3-

C6-cycloalkylaminocarbonyl and C3-C6-halocycloalkylaminocarbonyl,

or, together with the nitrogen atom to which they are bound, form a 5- or 6- membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further heteroatoms or heteroatom groups select- ed from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, CN, C1-C4- alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio and Ci-C4-haloalkylthio.

More preferably, R ^10a and R ^10b are in this case selected, independently of each other, from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci- C4-alkylaminocarbonyl and Ci-C4-haloalkylaminocarbonyl. Specifically, they are selected, independently of each other, from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and C3- C6-cycloalkyl. Very specifically, one of R ^10a and R ^10b is hydrogen and the other is C1-C4- alkyl, Ci-C4-haloalkyl or C3-C6-cycloalkyl.

In an alternative particular embodiment, in N(R ⁵ )R ⁶ as Y,

R ⁵ is hydrogen;

R ⁶ is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl which carries one radical R ⁸ , Cs-Ce-cycloalkyl,

phenyl which may be substituted with 1 , 2, 3, 4, or 5 substituents R ¹¹ , and a 4-, 5- or 6-membered saturated heteromonocyclic ring containing 1 heteroatom or heteroatom group selected from N, O, S, SO and SO2, as ring member or a 5- or 6- membered heteromonocyclic aromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteromonocyclic ring may be substituted with one or more substituents R ¹¹ , where the heteromonocyclic ring is preferably selected from rings of formulae F-1 to F-51 :

F-1 F-2 F-3 F-4 F-5

F-6 F-8 F-9

F-10 F-11 F F-13 F-14

F-25 F-26 F-27 F-28 F-29

F-50 F-51 wherein

k is 0, 1 , 2 or 3,

n is 0, 1 or 2, and

each R ¹¹ is independently selected from the group consisting of halogen, cy- ano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci- C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2- C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or two R ¹¹ present on the same carbon atom of a saturated ring may form to- gether =0 or =S;

R ⁸ is selected from Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Ci-C6-alkylthio, Ci- Ce-haloalkylthio, -C(=O)N(R ^10a )R ^10b , phenyl, optionally substituted with 1 , 2, 3, 4 or 5 substituents R ¹⁶ , and a heterocyclic ring selected from rings of formulae E-1 to E-51 as defined above;

wherein

R ^10a is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C3- alkynyl, -CH2-CIM and Ci-C6-alkoxy-methyl;

R ^10b is selected from the group consisting of hydrogen, Ci-C6-alkyl, C1-C6- haloalkyl, C3-C6-cycloalkyl, C3-C6-cyclohaloalkyl, phenyl which is op- tionally substituted with 1 , 2, 3, 4 or 5 substituents selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; and a heterocyclic ring selected from rings of formulae E-1 to E-51 as defined above; and

each R ¹⁶ as a substituent on phenyl or a heterocyclic ring E-1 to E-51 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci- C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or

two R ¹⁶ present on the same carbon atom of a saturated heterocyclic ring may form together =0 or =S;

or

R ⁵ and R ⁶ , together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated heterocyclic ring, where the ring may further contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, SO, SO2, NH and C=0 as ring members, wherein the heterocyclic ring may be substituted with 1 , 2 or 3 substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy, and preferably form a 5- or 6-membered saturated heterocyclic ring, wherein the heterocyclic ring may be substituted with 1 , 2 or 3 substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci- C6-alkoxy and Ci-C6-haloalkoxy.

Among the above rings, preference is given to F-44, F-48 and F-49. Particular preference is given to ring F-44 with n = 0 (thietan-3-yl) and its oxidized analogs with n = 1 and n = 2 (1 -oxo-thietan-3-yl and 1 ,1 -dioxo-thietan-3-yl).

Specifically, in A ² , W is O and Y is N(R ⁵ )R ⁶ , wherein

R ⁵ is selected from hydrogen and methyl, preferably hydrogen; and

R ⁶ is selected from Ci-C4-alkyl which carries one radical R ⁸ , preferably methyl which carries one radical R ⁸ ; Ci-C4-haloalkyl, and a 4-, 5- or 6-membered saturated heteromonocyclic ring containing 1 heteroatom or heteroatom group selected from S, SO and SO2, as ring member, where the heteromonocyclic ring may be substituted with one or more substituents R ¹¹ ;

wherein R ⁸ is selected from -C(=O)N(R ^10a )R ^10b , phenyl and a 5- or 6-membered heteroaromatic ring comprising 1 , 2 or 3 heteroatoms selected from N, O and S, as ring members, where the heteroaromatic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ , wherein

R ^10a and R ^10b are selected, independently of each other, from hydrogen, Ci-C ₄ -alkyl, Ci-C ₄ -haloalkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -haloalkenyl, C ₂ -C ₄ - alkynyl, C2-C ₄ -haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci- C ₄ -alkylcarbonyl, Ci-C ₄ -haloalkylcarbonyl, Ci-C ₄ -alkylaminocarbonyl, Ci-C ₄ -haloalkylaminocarbonyl, C3-C6-cycloalkylaminocarbonyl and C3-C6-halocycloalkylaminocarbonyl, and preferably from hydrogen, Ci-C ₄ -alkyl, Ci-C ₄ -haloalkyl and C3-C6-cycloalkyl, where it is preferred that one of R ^10a and R ^10b is hydrogen and the other is Ci-C ₄ -alkyl, Ci- C ₄ -haloalkyl or C3-C6-cycloalkyl;

each R ¹¹ is independently selected from halogen, cyano, nitro, Ci-C ₄ - alkyl, Ci-C ₄ -haloalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, Ci-C ₄ -alkylthio, Ci-C ₄ -haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C ₄ -haloalkenyl, C2-C ₄ -alkynyl and C2-C ₄ -haloalkynyl; and each R ¹⁶ is independently selected from halogen, cyano, nitro, C1-C4- alkyl, Ci-C ₄ -haloalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, Ci-C ₄ -alkylthio, Ci-C ₄ -haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C ₄ -haloalkenyl, C2-C ₄ -alkynyl and C2-C ₄ -haloalkynyl;

or

R ⁵ and R ⁶ , together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, CN, C1-C4- alkyl, Ci-C ₄ -haloalkyl, C2-C ₄ -alkenyl, C2-C ₄ -haloalkenyl, C2-C ₄ -alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C ₄ -alkoxy, C1-C4- haloalkoxy, Ci-C ₄ -alkylthio and Ci-C ₄ -haloalkylthio, and form preferably a 5- or 6- membered saturated heterocyclic ring (i.e. R ⁵ and R ⁶ form together -(CH2) ₄ - or - (CH2)5-), wherein the heterocyclic ring may be substituted with 1 , 2 or 3 substituents independently selected from the group consisting of halogen, cyano, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy.

Preferably the 4-, 5- or 6-membered saturated heteromonocyclic ring R ⁶ containing 1 heteroatom or heteroatom group selected from S, SO and SO2, as ring member is selected from rings D-72 (= F-44), D-77 (= F-48), D-78 (= F-49) and D-100 to D-102 listed below in context with A ⁴ . The ring may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹¹ as defined above. More preference is given to rings D-72 (= F-44), D-77 (= F-48) and D-78 (= F-49). Particular preference is given to ring D-72 (= F-44) with n = 0 (thietan-3-yl) and its oxidized analogs with n = 1 and n = 2 (1 -oxo-thietan-3-yl and 1 ,1 -dioxo-thietan-3-yl).

Preferably the 5- or 6-membered heteroaromatic ring comprising 1 , 2 or 3 heteroatoms selected from N, O and S, as ring members is selected from rings E-1 to E-42 as defined above. The ring may be substituted with one or more, preferably 1 , 2 or 3, in par- ticular 1 , substituents R ¹⁶ selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl. In an alternative embodiment of the invention, A is A ³ .

Preferably, R ^7a and R ^7b in the group A ³ are independently of each other selected from hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl, and more preferably one of R ^7a and R ^7b is hydrogen and the other is hydrogen or methyl. Specifically, both are hydrogen.

In the group A ³ ,

R ⁵ is preferably selected from hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ⁸ ; and

R ⁶ is preferably selected from hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ⁸ ,

-OR ⁹ , -NR ^10a R ^10b , -S(0) _n R ⁹ , -C(=O)NR ^0a N(R ^0a R ^0b ), -C(=0)R ⁸ ,

and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹¹ ;

or

R ⁵ and R ⁶ , together with the nitrogen atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated het- erocyclic ring, where the ring may further contain 1 , 2, 3 or 4 heteroatoms or het- eroatom-containing groups selected from O, S, N, SO, SO2, C=0 and C=S as ring members, wherein the heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, wherein the aliphatic or cycloaliphatic moieties in the twelve last- mentioned radicals may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ⁸ , and phenyl which may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R ¹¹ ;

or

R ⁵ and R ⁶ together form a group =C(R ⁸ ) ₂ , =S(0) _m (R ⁹ ) ₂ , =NR ^10a or =NOR ⁹ wherein R ⁸ , R ⁹ , R ^10a , R ^10b and R ¹¹ have one of the above general meanings, or, in particular, one of the below preferred meanings.

More preferably, in the group A ³ ,

R ⁵ is selected from hydrogen, Ci-C4-alkyl, which may be partially or fully halogenat- ed and/or may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ⁸ selected from cyano and Ci-C6-alkoxy; and C2-C4-alkynyl; and

R ⁶ is selected from -S(0) _n R ⁹ and -C(=0)R ⁸ ,

or

R ⁵ and R ⁶ , together with the nitrogen atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated het- erocyclic ring, where the ring may further contain 1 , 2, 3 or 4 heteroatoms or het- eroatom-containing groups selected from O, S, N, SO, SO2, C=0 and C=S as ring members, wherein the heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl,

C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, wherein the aliphatic or cycloaliphatic moieties in the twelve last- mentioned radicals may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ⁸ , and phenyl which may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R ¹¹ ;

wherein R ⁸ , R ⁹ , R ^10a , R ^10b and R ¹¹ have one of the above general meanings, or, in particular, one of the below preferred meanings.

Even more preferably, in the group A ³ , is selected from hydrogen, Ci-C4-alkyl, C2-C3-alkynyl, CH2-CN and Ci-C6-alkoxy- methyl-, preferably from hydrogen and Ci-C4-alkyl; and

is -C(=0)R ⁸ ;

wherein R ⁸ has one of the above general meanings, or, in particular, one of the below preferred meanings.

R ⁸ in -C(=0)R ⁸ as a meaning of the radicals R ⁵ and R ⁶ of the group A ³ is preferably selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C ₀ -cycloalkyl, C3- Co-halocycloalkyl, where the aliphatic and cycloaliphatic moieties in the four last- mentioned radicals may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ¹³ ;

-OR ⁹ , -S(0) _n R ⁹ , -N(R ^0a )R ^0b ,

phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ , and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroa- tom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹⁶ ,

wherein R ⁹ , R ^10a , R ^10b , R ¹³ and R ¹⁶ have one of the above general meanings, or, in par- ticular, one of the below preferred meanings.

More preferably, R ⁸ in -C(=0)R ⁸ as a meaning of the radicals R ⁵ and R ⁶ of the group A ³ is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl substituted by one radical R ¹³ , C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -halocycloalkyl, -N(R ^10a )R ^10b , phenyl which is optionally substituted with 1 , 2, 3, 4 or 5 substituents each independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3- C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; and a heterocyclic ring selected from rings of formulae E-1 to E-51 as defined above.

R ⁹ in -OR ⁹ as a meaning of R ⁸ in the group -C(=0)R ⁸ as a meaning of the radicals R ⁵ and R ⁶ of the group A ³ is preferably selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C ₀ - halocycloalkyl and C3-C8-cycloalkyl-Ci-C4-alkyl-, and more preferably from Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl and C3-C ₀ -cycloalkyl-Ci-C4- alkyk R ^10a and R ^10b in -N(R ^10a )R ^10b as a meaning of R ⁸ in the group -C(=0)R ⁸ as a meaning of the radicals R ⁵ and R ⁶ of the group A ³ are, independently of each other, preferably selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkyl substituted by one radical R ¹³ , C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, C1-C4- alkylaminocarbonyl, Ci-C4-haloalkylaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, C3- C6-halocycloalkylaminocarbonyl, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroa- toms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and C1-C4- haloalkylthio;

or, R ^10a and R ^10b , together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C2- C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3- C6-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and C1-C4- haloalkylthio.

More preferably, R ^10a and R ^10b in R ⁸ in the radicals R ⁵ and R ⁶ of the group A ³ are, inde- pendently of each other, selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkyl substituted by one radical R ¹³ , C3-C6-cycloalkyl, C3-C6-halocycloalkyl, and a 3- or 4-membered saturated heterocyclic ring comprising 1 heteroatom or heteroatom group selected from N, O, S, NO, SO and SO2, as ring member, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy; and are specifically, independently of each other, selected from hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl.

R ¹³ in R ⁸ in the radicals R ⁵ and R ⁶ of the group A ³ is preferably selected from CN, Ci- C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci- C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl and Ci-C6-haloalkylsulfonyl.

R ¹⁶ in R ⁸ in the radicals R ⁵ and R ⁶ of the group A ³ is preferably selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy. Specifically, R ⁸ in the group -C(=0)R ⁸ in the radicals R ⁵ and R ⁶ of the group A ³ is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl substituted by one radical R ¹³ , C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -halocycloalkyl, -N(R ^10a )R ^10b , phenyl which is optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3 and in particular 1 , substituents each independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci- C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl, and a heterocyclic ring selected from rings of formulae E-1 to E-51 as defined above, wherein

R ^10a and R ^10b , independently of each other, are selected from hydrogen, Ci-C4-alkyl,

Ci-C4-haloalkyl and C3-C6-cycloalkyl;

R ¹³ is selected from CN, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci- C6-haloalkylsulfonyl and a heterocyclic ring selected from rings of formulae E-1 to

E-51 as defined above and preferably from Ci-C6-alkylthio, Ci-C6-haloalkylthio,

Ci-C6-alkylsulfonyl and Ci-C6-haloalkylsulfonyl; and

each R ¹⁶ as a substituent on heterocyclic rings of formulae E-1 to E-51 is independently selected from the group consisting of halogen, cyano, nitro, C1-C4- alkyl, Ci-C ₄ -haloalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, Ci-C ₄ -alkylthio, C1-C4- haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or

two R ¹⁶ present on the same carbon atom of a saturated heterocyclic ring may form together =0 or =S.

More specifically, R ⁸ in the group -C(=0)R ⁸ in the radicals R ⁵ and R ⁶ of the group A ³ is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl substituted by one radical R ¹³ , Cs-Cs-cycloalkyl and Cs-Cs-halocycloalkyl, where R ¹³ is selected from CN, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, preferably from Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl and C1-C6- haloalkylsulfonyl and in particular from Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfonyl and Ci-C6-haloalkylsulfonyl. Alternatively, in the group A ³ , R ⁵ and R ⁶ are in particular hydrogen.

In an alternative embodiment of the invention, A is A ⁴ . A ⁴ is preferably selected from a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹¹ , where R ¹¹ has one of the above general meanings, or, in particular, one of the below preferred meanings.

More preferably, A ⁴ is selected from a 3-, 4-, 5-, 6- or 7-membered saturated heteromonocyclic ring containing 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, a 5-, 6- or 7-membered partially unsaturated heteromonocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, and a 5- or 6-membered aromatic heteromonocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring members, where the heteromonocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R ¹¹ , where R ¹¹ has one of the above general meanings, or, in particular, one of the below preferred meanings.

A ⁴ is even more preferably selected from rings of formulae D-1 to D-173

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

D-6 D-7 D-8 D-9 D-10

D-1 1 D-12 D-13 D-14

D-15 D-16 D-17 D-18 D-19

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

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

D-65 D-66 D-67 D-68 D-69

D-70 D-71 D-72 D-73 D-74

D-75 D-76 D-77 D-78 D-79

D-80 D-81 D-82 D-83 D-84

D-85 D-87 D-88 D-89

D-90 D-91 D-92 D-93 D-94

D-95 D-96 D-97 D-98 D-99

D-100 D-101 D-102 D-103 D-104

D-105 D-106 D-107 D-108 -109

D-120 D-121 D-122 D-123 D-124

D-125 D-126 D-127 D-128 D-129

D-130 D-131 D-132 D-133 D-134

D-135 D-136 D-137 D-138 D-139

D-155 D-156 D-157 D-158 D-159

D-160 D-161 D-162 D-163 D-164 ¹¹ )

D-170 D-171 D-172 D-173 wherein k is 0, 1 , 2 or 3, n is 0, 1 or 2 and R ^{1 1} has one of the above general meanings, or, in particular, one of the below preferred meanings;

and is in particular selected from D-59, D-65 and D-66 and is specifcally D-59.

Preferably, in the above rings D-1 to D-173,

each R ^{1 1} is independently selected from the group consisting of halogen, cyano, ni- tro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or

two R ^{1 1} present on the same carbon atom of a saturated or partially unsaturated ring may form together =0 or =S.

Among the radicals A ¹ , A ² , A ³ and A ⁴ , preference is given to A ² .

Preferably, B ¹ , B ² and B ³ are CR ² .

More preferably, B ¹ and B ³ are CR ² , where R ² is not hydrogen, and B ² is CR ² , where R ² has one of the meanings given above.

Preferably, R ² is selected from hydrogen, halogen, cyano, azido, nitro, -SCN , SF ₅ , Ci- C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ⁸ , -OR ⁹ , -S(0) _n R ⁹ and -N R ^10a R ^10b ,

wherein R ⁸ , R ⁹ , R ^10a and R ^10b have one of the above general meanings, or, in particular, one of the below preferred meanings. More preferably, R ² is selected from hydrogen, halogen and Ci-C2-haloalkyl, even more preferably from hydrogen, F, CI, Br and CF3, even more preferably from hydrogen, F, CI and CF3, and in particular from hydrogen and CI. Specifically, B ² is CH and B ¹ and B ³ have one of the general or one of the preferred meanings given above for R ² (with the proviso that they are not hydrogen) and are preferably selected from halogen and Ci-C2-haloalkyl, even more preferably from F, CI, Br and CF3, particularly preferably from hydrogen, F, CI and CF3, and are in particular CI.

Alternatively, B ² is CF or CCI and B ¹ and B ³ have one of the general or one of the preferred meanings given above for R ² (with the proviso that they are not hydrogen) and are preferably selected from halogen and Ci-C2-haloalkyl, such as F, CI and CF3, even more preferably from F and CI, and are in particular CI.

Preferably, G ¹ , G ³ and G ⁴ are CR ⁴ and G ² is N or CR ⁴ , where R ⁴ has one of the meanings given above or below; or G ² , G ³ and G ⁴ are CR ⁴ and G ¹ is N or CR ⁴ , where R ⁴ has one of the meanings given above or below. Preferably, R ⁴ is selected from hydrogen, halogen, cyano, azido, nitro, Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ⁸ , Cs-Cs-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ⁸ , C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ⁸ , C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R ⁸ , -OR ⁹ , -S(0) _n R ⁹ , and -NR ^10a R ^10b . More preferably, R ⁴ is selected from hydrogen, halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, and even more preferably from hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio and Ci-C4-haloalkylthio, and specifically from hydrogen, methyl and CF3.

More preferably, G ¹ , G ³ and G ⁴ are CH and G ² is CR ⁴ , where R ⁴ has one of the above general or preferred meanings; or G ¹ is N, G ³ and G ⁴ are CH and G ² is CR ⁴ . In another embodiment, G ¹ and G ⁴ are CR ⁴ and G ² and G ³ are CH, where R ⁴ has one of the meanings given above or below. Even more preferably, G ¹ , G ³ and G ⁴ are CH and G ² is CR ⁴ , where R ⁴ is selected from hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio and Ci-C4-haloalkylthio, preferably from hydrogen, F, CI, CN, methyl, CF3, methoxy and methylthio, and specifically from hydrogen, F, CI, CN, methyl methoxy and methylthio.

Alternatively, even more preferably, G ¹ is N, G ² is CR ⁴ and G ³ and G ⁴ are CH, where R ⁴ is selected from hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and Ci-C4-haloalkylthio, preferably from hydrogen, F, CI, CN, methyl, CF3, methoxy and methylthio, and specifically from hydro- gen and methyl.

Preferably, R ¹ is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C ₄ -haloalkoxy-Ci-C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl C ₃ -C ₆ -halocycloalkyl or C(=0)OR ¹³ ; more preferably, from Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl and C(=0)OR ¹⁵ , even more preferably from Ci-C4-alkyl, Ci-C4-haloalkyl and -C(=0)OR ¹⁵ , and particularly preferably from Ci-C ₄ -haloalkyl and -C(=0)OR ¹⁵ , wherein R ¹⁵ is preferably Ci-C4-alkyl. In particular, R ¹ is Ci-C4-haloalkyl, specifically Ci- C2-haloalkyl and more specifically halomethyl, in particular fluoromethyl, such as fluo- romethyl, difluoromethyl and trifluoromethyl, and is very specifically trifluoromethyl.

Preferably, R ^3a and R ^3b are selected, independently of each other, from hydrogen, halogen, hydroxyl, Ci-C3-alkyl, Ci-C3-alkenyl, Ci-C3-alkynyl, Ci-C3-haloalkyl, Ci-C3-alkoxy, Ci-C3-alkylthio and Ci-C3-alkylsulfonyl, more preferably from hydrogen and halogen, in particular from hydrogen and fluorine and are specifically hydrogen.

If not specified otherwise above, R ⁸ , R ⁹ , R ^10a , R ^10b , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ^14a , R ^14b , R ¹⁵ and R ¹⁶ have following preferred meanings:

In case R ⁸ is a substituent on an alkyl, alkenyl or alkynyl group, it is preferably selected from the group consisting of cyano, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, -OR ⁹ , -SR ⁹ , -C(=O)N(R ^0a )R ^0b , -C(=S)N(R ^0a )R ⁰ , -C(=0)OR ⁹ , phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R ¹⁶ , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocy- die ring may be substituted by one or more radicals R ¹⁶ ; where R ⁹ , R ^10a , R ^10b and R ¹⁶ have one of the meanings given above or in particular one of the preferred meanings given below. In case R ⁸ is a substituent on an alkyl, alkenyl or alkynyl group, it is even more preferably selected from the group consisting of cyano, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, Ci-C ₄ -alkylthio, Ci-C ₄ -haloalkylthio, -C(=O)N(R ^10a )R ^10b , -C(=S)N(R ^10a )R ^10b , -C(=0)OR ⁹ , phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R ¹⁶ , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R ¹⁶ ; where R ⁹ , R ^10a , R ^10b and R ¹⁶ have one of the meanings given above or in particular one of the preferred meanings given below. In particular it is selected from the group consisting of cyano, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, -C(=O)N(R ^0a )R ⁰ , -C(=S)N(R ^0a )R ⁰ , -C(=0)OR ⁹ , phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R ¹⁶ , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R ¹⁶ ; where R ⁹ , R ^10a , R ^10b and R ¹⁶ have one of the meanings given above or in particular one of the preferred meanings given below.

In case R ⁸ is a substituent on a cycloalkyl group, it is preferably selected from the group consisting of cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci-C6-alkyl, -OR ⁹ , -OSO2R ⁹ , -SR ⁹ , -N(R ^0a )R ⁰ , -C(=O)N(R ^0a )R ⁰ , -C(=S)N(R ^0a )R ⁰ , -C(=0)OR ⁹ , phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R ¹⁶ , and a 3-, 4-, 5-, 6- or 7- membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R ¹⁶ ; where R ⁹ , R ^10a , R ^10b and R ¹⁶ have one of the meanings given above or in particular one of the preferred meanings given below.

In case R ⁸ is a substituent on a cycloalkyl group, it is even more preferably selected from the group consisting of halogen, Ci-C ₄ -alkyl, Ci-C3-haloalkyl, Ci-C ₄ -alkoxy and Ci-C3-haloalkoxy. In particular, R ⁸ as a substituent on a cycloalkyl group is selected from halogen, Ci-C ₄ -alkyl and Ci-C3-haloalkyl.

In case of R ⁸ in a group -C(=0)R ⁸ , =C(R ⁸ ) ₂ or -C(=NR ⁶ )R ⁸ , R ⁸ is preferably selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci- C6-alkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- Ce-alkynyl, C ₂ -C ₆ -haloalkynyl, -OR ⁹ , -SR ⁹ , -N(R ^10a )R ^10b , phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R ¹⁶ , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroa- torn groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R ¹⁶ ; where R ⁹ , R ^10a , R ^10b and R ¹⁶ have one of the meanings given above or in particular one of the preferred meanings given below. In case of R ⁸ in a group -C(=0)R ⁸ , =C(R ⁸ ) ₂ or -C(=NR ⁶ )R ⁸ , R ⁸ is more preferably selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs- Cs-halocycloalkyl, d-Ce-alkoxy, Ci-C ₆ -haloalkoxy, -N(R ^10a )R ^10b , phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R ¹⁶ , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R ¹⁶ ; where R ^10a , R ^10b and R ¹⁶ have has one of the meanings given above or in particular one of the preferred meanings given below. Preferably, each R ⁹ is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkyl- Ci-C4-alkyl, phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R ¹⁶ ; and a 3-, 4- , 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1 , 2, 3 or 4, preferably 1 or 2, more preferably 1 , radicals R ¹⁶ , where R ¹⁶ has one of the meanings given above or in particular one of the preferred meanings given below. More preferably, each R ⁹ is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R ¹⁶ ; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S, as ring members, where the heteroaromatic ring may be substituted by one or more radicals R ¹⁶ ; where R ¹⁶ has one of the meanings given above or in particular one of the preferred meanings given below.

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

or, R ^10a and R ^10b , together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and S0 ₂ , as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C ₂ - C4-alkenyl, C ₂ -C4-haloalkenyl, C ₂ -C4-alkynyl, C ₂ -C4-haloalkynyl, C3-C6-cycloalkyl, C3- C6-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and C1-C4- haloalkylthio.

More preferably, R ^10a and R ^10b are, independently of each other, selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, and a 3- or 4-membered saturated heterocyclic ring comprising 1 heteroatom or heteroatom group selected from N, O, S, NO, SO and S0 ₂ , as ring member, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents selected from halogen, CN , Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci- C4-haloalkoxy; and are specifically, independently of each other, selected from hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl.

Each R ¹¹ and each R ¹⁶ are independently of each occurrence and independently of each other preferably selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, C1-C4- haloalkylsulfinyl, Ci-C4-alkylsulfonyl and Ci-C4-haloalkylsulfonyl, and more preferably from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

Each R ¹² is preferably selected from Ci-C4-alkyl and is in particular methyl.

In case R ¹³ is a substituent on an alkyl, alkenyl or alkynyl group, it is preferably selected from the group consisting of cyano, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, -OH, - SH, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl and phenyl which may be substituted by 1 , 2 or 3 radicals selected from halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

In case R ¹³ is a substituent on a cycloalkyl group, it is preferably selected from the group consisting of cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, -OH, -SH, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, C1-C4- haloalkylsulfonyl and phenyl which may be substituted by 1 , 2 or 3 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

In case R ¹³ is a substituent on a cycloalkyl group, it is even more preferably selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C3-haloalkyl, Ci-C4-alkoxy and Ci-C3-haloalkoxy. In particular, R ¹³ as a substituent on a cycloalkyl group is selected from halogen, Ci-C4-alkyl and Ci-C3-haloalkyl.

In case of R ¹³ in a group -C(=0)R ¹³ , -C(=S)R ¹³ , =C(R ¹³ ) ₂ or -C(=NR ⁴ )R ¹³ , R ⁸ is preferably selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs- Cs-cycloalkyl, C3-Cs-halocycloalkyl, -OH, -SH, Ci-C6-alkoxy, Ci-C6-haloalkoxy and phenyl which may be substituted by 1 , 2 or 3 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.

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

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

More preferably, R ¹⁴ , R ^14a and R ^14b are, independently of each other, selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and benzyl, where the phenyl ring in benzyl is optionally substituted 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci- C4-haloalkoxy; or, R ^14a and R ^14b , together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy.

Each R ¹⁵ is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may be unsubsti- tuted and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci- C6-alkoxy and Ci-C6-haloalkoxy.

In a particular embodiment of the invention, compound I is a compound of formula IA

where A, R ² and R ⁴ have one of the above-given general or, in particular, one of the above-given preferred meanings, and R ^2a and R ^2c , independently of each other, have one of the general or, in particular, one of the preferred meanings given above for R ² , with the proviso that they are not hydrogen, and are specifically CI or CF3 and are very specifically CI.

Examples of preferred compounds are compounds of the following formulae la.1 to la.31 , where the variables have one of the general or preferred meanings given above. Examples of preferred compounds are the individual compounds compiled in the tables 1 to 2082 below, Moreover, the meanings mentioned below for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question. 70

Table 1

Compounds of the formula la.1 in which R ^14b is hydrogen, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2

Compounds of the formula la.1 in which R ^14b is methyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 3

Compounds of the formula la.1 in which R ^14b is ethyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 4

Compounds of the formula la.1 in which R ^14b is propyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 5

Compounds of the formula la.1 in which R ^14b is isopropyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 6

Compounds of the formula la.1 in which R ^14b is n-butyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 7

Compounds of the formula la.1 in which R ^14b is sec-butyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 8

Compounds of the formula la.1 in which R ^14b is isobutyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 9

Compounds of the formula la.1 in which R ^14b is tert-butyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 10

Compounds of the formula la.1 in which R ^14b is isopropenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1 1

Compounds of the formula la.1 in which R ^14b is cyclopropyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 12

Compounds of the formula la.1 in which R ^14b is 2,2-difluoroethyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 13

Compounds of the formula la.1 in which R ^14b is 2,2,2-trifluoroethyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 14

Compounds of the formula la.1 in which R ^14b is 3,3,3-trifluoropropyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 15

Compounds of the formula la.1 in which R ^14b is Chb-CN, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 16

Compounds of the formula la.1 in which R ^14b is Chb-isopropenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 17

Compounds of the formula la.1 in which R ^14b is Chb-cyclopropyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 18

Compounds of the formula la.1 in which R ^14b is thietan-3-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 19

Compounds of the formula la.1 in which R ^14b is 1 -oxo-thietan-3-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 20

Compounds of the formula la.1 in which R ^14b is 1 ,1 -dioxo-thietan-3-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 21

Compounds of the formula la.1 in which R ^14b is allyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 22

Compounds of the formula la.1 in which R ^14b is propargyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 23

Compounds of the formula la.1 in which R ^14b is methoxy, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 24

Compounds of the formula la.1 in which R ^14b is ethoxy, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 25

Compounds of the formula la.1 in which R ^14b is isopropoxy, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Tables 26 to 50

Compounds of the formula la.2 in which R ^14b is as defined in any of tables 1 to 25 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 51 to 75

Compounds of the formula la.3 in which R ^14b is as defined in any of tables 1 to 25 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 76 to 100

Compounds of the formula la.4 in which R ^14b is as defined in any of tables 1 to 25 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 101 to 125

Compounds of the formula la.5 in which R ^14b is as defined in any of tables 1 to 25 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 126 to 150

Compounds of the formula la.6 in which R ^14b is as defined in any of tables 1 to 25 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 151 to 175

Compounds of the formula la.7 in which R ^14b is as defined in any of tables 1 to 25 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 176 to 200

Compounds of the formula la.8 in which R ^14b is as defined in any of tables 1 to 25 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 201 Compounds of the formula la.9 in which R ^10b is phenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 202

Compounds of the formula la.9 in which R ^10b is 2-fluorophenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 203

Compounds of the formula la.9 in which R ^10b is 3-fluorophenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 204

Compounds of the formula la.9 in which R ^10b is 4-fluorophenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 205

Compounds of the formula la.9 in which R ^10b is 2-chlorophenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 206

Compounds of the formula la.9 in which R ^10b is 3-chlorophenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 207

Compounds of the formula la.9 in which R ^10b is 4-chlorophenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 208

Compounds of the formula la.9 in which R ^10b is 2,3-difluorophenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 209

Compounds of the formula la.9 in which R ^10b is 2,4-difluorophenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 210

Compounds of the formula la.9 in which R ^10b is 2,5-difluorophenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 21 1

Compounds of the formula la.9 in which R ^10b is 2,6-difluorophenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 212

Compounds of the formula la.9 in which R ^10b is 3,4-difluorophenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 213

Compounds of the formula la.9 in which R ^10b is 3,5-difluorophenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 214 Compounds of the formula la.9 in which R ^10b is 3,4,5-trifluorophenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 215

Compounds of the formula la.9 in which R ^10b is 2,4-dichlorophenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 216

Compounds of the formula la.9 in which R ^10b is 3,5-dichlorophenyl, and the combina- tion of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 217

Compounds of the formula la.9 in which R ^10b is 2-methylphenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 218

Compounds of the formula la.9 in which R ^10b is 3-methylphenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 219

Compounds of the formula la.9 in which R ^10b is 4-methylphenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 220

Compounds of the formula la.9 in which R ^10b is 2-methoxyphenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 221

Compounds of the formula la.9 in which R ^10b is 3-methoxyphenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 222

Compounds of the formula la.9 in which R ^10b is 4-methoxyphenyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 223

Compounds of the formula la.9 in which R ^10b is pyridin-2-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 224

Compounds of the formula la.9 in which R ^10b is 3-chloropyridin-2-yl, and the combina- tion of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 225 Compounds of the formula la.9 in which R ^10b is 4-chloropyridin-2-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 226

Compounds of the formula la.9 in which R ^10b is 5-chloropyridin-2-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 227

Compounds of the formula la.9 in which R ^10b is 6-chloropyridin-2-yl, and the combina- tion of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 228

Compounds of the formula la.9 in which R ^10b is 3-methoxypyridin-2-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 229

Compounds of the formula la.9 in which R ^10b is 4-methoxypyridin-2-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 230

Compounds of the formula la.9 in which R ^10b is 5-methoxypyridin-2-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 231

Compounds of the formula la.9 in which R ^10b is 6-methoxypyridin-2-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 232

Compounds of the formula la.9 in which R ^10b is pyridin-3-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 233

Compounds of the formula la.9 in which R ^10b is 2-chloropyridin-3-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 234

Compounds of the formula la.9 in which R ^10b is 4-chloropyridin-3-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 235 Compounds of the formula la.9 in which R ^10b is 5-chloropyridin-3-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 236

Compounds of the formula la.9 in which R ^10b is 6-chloropyridin-3-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 237

Compounds of the formula la.9 in which R ^10b is 2-methoxypyridin-3-yl, and the combi- nation of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 238

Compounds of the formula la.9 in which R ^10b is 4-methoxypyridin-3-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 239

Compounds of the formula la.9 in which R ^10b is 5-methoxypyridin-3-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 240

Compounds of the formula la.9 in which R ^10b is 6-methoxypyridin-3-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 241

Compounds of the formula la.9 in which R ^10b is pyridin-4-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 242

Compounds of the formula la.9 in which R ^10b is 2-chloropyridin-4-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 243

Compounds of the formula la.9 in which R ^10b is 3-chloropyridin-4-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 244

Compounds of the formula la.9 in which R ^10b is 2-methoxypyridin-4-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 245 Compounds of the formula la.9 in which R ^10b is 3-methoxypyridin-4-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 246

Compounds of the formula la.9 in which R ^10b is pyrimidin-2-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 247

Compounds of the formula la.9 in which R ^10b is pyrimidin-4-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 248

Compounds of the formula la.9 in which R ^10b is pyrimidin-5-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 249

Compounds of the formula la.9 in which R ^10b is pyrrol-2-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 250

Compounds of the formula la.9 in which R ^10b is pyrrol-3-yl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 251

Compounds of the formula la.9 in which R ^10b is hydrogen, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 252

Compounds of the formula la.9 in which R ^10b is methyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 253

Compounds of the formula la.9 in which R ^10b is ethyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 254

Compounds of the formula la.9 in which R ^10b is isopropyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 255

Compounds of the formula la.9 in which R ^10b is methylcarbonyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 256

Compounds of the formula la.9 in which R ^10b is ethylcarbonyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 257

Compounds of the formula la.9 in which R ^10b is isopropylcarbonyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 258

Compounds of the formula la.9 in which R ^10b is methoxycarbonyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 259

Compounds of the formula la.9 in which R ^10b is ethoxycarbonyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 260

Compounds of the formula la.9 in which R ^10b is isopropoxycarbonyl, and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 261 to 320

Compounds of the formula la.10 in which R ^10b is as defined in any of tables 201 to 260 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 321 to 380

Compounds of the formula la.1 1 in which R ^10b is as defined in any of tables 201 to 260 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 381 to 440

Compounds of the formula la.12 in which R ^10b is as defined in any of tables 201 to 260 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 441

Compounds of the formula la.13 in which R ⁶ is hydrogen and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 442

Compounds of the formula la.13 in which R ⁶ is methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 443

Compounds of the formula la.13 in which R ⁶ is ethyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 444

Compounds of the formula la.13 in which R ⁶ is propyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 445

Compounds of the formula la.13 in which R ⁶ is isopropyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 446 Compounds of the formula la.13 in which R ⁶ is n-butyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 447

Compounds of the formula la.13 in which R ⁶ is sec-butyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 448

Compounds of the formula la.13 in which R ⁶ is isobutyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 449

Compounds of the formula la.13 in which R ⁶ is tert-butyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 450

Compounds of the formula la.13 in which R ⁶ is CH2-C(CH3)3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 451

Compounds of the formula la.13 in which R ⁶ is -CH2CIM and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 452

Compounds of the formula la.13 in which R ⁶ is -CH2-CH=CH2 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 453

Compounds of the formula la.13 in which R ⁶ is -CH2C≡CH and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 454

Compounds of the formula la.13 in which R ⁶ is CH2CH2OH and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 455

Compounds of the formula la.13 in which R ⁶ is -CH2CH2OCH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 456

Compounds of the formula la.13 in which R ⁶ is -CH2CH2OCH2CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 457

Compounds of the formula la.13 in which R ⁶ is -CH2CH2OCF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 458

Compounds of the formula la.13 in which R ⁶ is -CH2CH2OCH2CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 459 Compounds of the formula la.13 in which R ⁶ is -CH(CH3)CH20CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 460

Compounds of the formula la.13 in which R ⁶ is -CH(CH3)CH20CH ₂ CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 461

Compounds of the formula la.13 in which R ⁶ is -CH2CH2SCH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 462

Compounds of the formula la.13 in which R ⁶ is -CH2CH2S(0)CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 463

Compounds of the formula la.13 in which R ⁶ is -CH2CH2S(0)2CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 464

Compounds of the formula la.13 in which R ⁶ is -CH2CH2SCH2CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 465

Compounds of the formula la.13 in which R ⁶ is -CH2CH2S(0)CH2CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 466

Compounds of the formula la.13 in which R ⁶ is -ChbChbS D^CI-bCHs and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 467

Compounds of the formula la.13 in which R ⁶ is -CH(CH3)CH2SCH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 468

Compounds of the formula la.13 in which R ⁶ is -CH(CH3)CH ₂ S(0)CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 469

Compounds of the formula la.13 in which R ⁶ is -CH(CH3)CH ₂ S(0)2CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 470 Compounds of the formula la.13 in which R ⁶ is -C(CH3)2CH2SCH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 471

Compounds of the formula la.13 in which R ⁶ is -C(CH3)2CH2S(0)CH3 and the combina- tion of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 472

Compounds of the formula la.13 in which R ⁶ is -C(CH3)2CH2S(0)2CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 473

Compounds of the formula la.13 in which R ⁶ is -CH2CH2SCF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 474

Compounds of the formula la.13 in which R ⁶ is CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 475

Compounds of the formula la.13 in which R ⁶ is CH2CHF2 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 476

Compounds of the formula la.13 in which R ⁶ is CH2CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 477

Compounds of the formula la.13 in which R ⁶ is CH2CH2CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 478

Compounds of the formula la.13 in which R ⁶ is CH(CH3)CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 479

Compounds of the formula la.13 in which R ⁶ is CH(CF3)2 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 480

Compounds of the formula la.13 in which R ⁶ is CH2CH2CH2CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 481

Compounds of the formula la.13 in which R ⁶ is CH2CH2CH=CF2 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 482 Compounds of the formula la.13 in which R ⁶ is CH2CH2CF=CF2 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 483

Compounds of the formula la.13 in which R ⁶ is cyclopropyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 484

Compounds of the formula la.13 in which R ⁶ is 1 -cyano-cyclopropyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 485

Compounds of the formula la.13 in which R ⁶ is 1 -(pyridin-2-yl)-cyclopropyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 486

Compounds of the formula la.13 in which R ⁶ is cyclobutyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 487

Compounds of the formula la.13 in which R ⁶ is cyclopentyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 488

Compounds of the formula la.13 in which R ⁶ is cyclohexyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 489

Compounds of the formula la.13 in which R ⁶ is -Chb-cyclopropyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 490

Compounds of the formula la.13 in which R ⁶ is -CH2-(1 -cyano-cyclopropyl) and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 491

Compounds of the formula la.13 in which R ⁶ is -CH2-(2,2-difluorocyclopropyl) and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 492

Compounds of the formula la.13 in which R ⁶ is -CH2-(2,2-dichlorocyclopropyl) and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 493 Compounds of the formula la.13 in which R ⁶ is -Chb-cyclobutyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 494

Compounds of the formula la.13 in which R ⁶ is -CH2-(2,2-difluorocyclobutyl) and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 495

Compounds of the formula la.13 in which R ⁶ is -Chb-cyclopentyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 496

Compounds of the formula la.13 in which R ⁶ is -Chb-cyclohexyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 497

Compounds of the formula la.13 in which R ⁶ is 1 ,1-difluorocyclobut-3-yl and the combi- nation of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 498

Compounds of the formula la.13 in which R ⁶ is -CH2-1 ,1 -difluorocyclobut-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 499

Compounds of the formula la.13 in which R ⁶ is thietan-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 500

Compounds of the formula la.13 in which R ⁶ is 1 -oxo-thietan-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 501

Compounds of the formula la.13 in which R ⁶ is 1 ,1-dioxo-thietan-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 502

Compounds of the formula la.13 in which R ⁶ is 3-methyl-thietan-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 503

Compounds of the formula la.13 in which R ⁶ is 3-methyl-1 -oxo-thietan-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 504 Compounds of the formula la.13 in which R ⁶ is 3-methyl-1 ,1 -dioxo-thietan-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 505

Compounds of the formula la.13 in which R ⁶ is -CH2-thietan-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 506

Compounds of the formula la.13 in which R ⁶ is -CH2-(1 -oxo-thietan-3-yl) and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 507

Compounds of the formula la.13 in which R ⁶ is -CH2-(1 ,1 -dioxo-thietan-3-yl) and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 508

Compounds of the formula la.13 in which R ⁶ is tetrahydrothiophen-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 509

Compounds of the formula la.13 in which R ⁶ is 1 -oxo-tetrahydrothiophen-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 510

Compounds of the formula la.13 in which R ⁶ is 1 ,1-dioxo-tetrahydrothiophen-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 51 1

Compounds of the formula la.13 in which R ⁶ is phenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 512

Compounds of the formula la.13 in which R ⁶ is 2-nitrophenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 513

Compounds of the formula la.13 in which R ⁶ is pyridin-2-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 514

Compounds of the formula la.13 in which R ⁶ is pyridin-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 515 Compounds of the formula la.13 in which R ⁶ is pyridin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 516

Compounds of the formula la.13 in which R ⁶ is pyrimidin-2-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 517

Compounds of the formula la.13 in which R ⁶ is pyrimidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 518

Compounds of the formula la.13 in which R ⁶ is pyrimidin-5-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 519

Compounds of the formula la.13 in which R ⁶ is thiazol-2-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 520

Compounds of the formula la.13 in which R ⁶ is 4-trifluoromethylthiazol-2-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 521

Compounds of the formula la.13 in which R ⁶ is oxetan-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 522

Compounds of the formula la.13 in which R ⁶ is tetrahydrofuran-2-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 523

Compounds of the formula la.13 in which R ⁶ is tetrahydrofuran-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 524

Compounds of the formula la.13 in which R ⁶ is 2-oxotetrahydrofuran-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 525

Compounds of the formula la.13 in which R ⁶ is 2-oxopyrrolidin-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 526 Compounds of the formula la.13 in which R ⁶ is 1 -methyl-2-oxopyrrolidin-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 527

Compounds of the formula la.13 in which R ⁶ is 2-oxo-1 -(2,2,2-trifluoroethyl)-pyrrolidin- 3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 528

Compounds of the formula la.13 in which R ⁶ is azetidin-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 529

Compounds of the formula la.13 in which R ⁶ is 1 -acetyl-azetidin-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 530

Compounds of the formula la.13 in which R ⁶ is -NH-phenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 531

Compounds of the formula la.13 in which R ⁶ is -NH-pyridin-2-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 532

Compounds of the formula la.13 in which R ⁶ is -NH-pyridin-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 533

Compounds of the formula la.13 in which R ⁶ is -NH-pyridin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 534

Compounds of the formula la.13 in which R ⁶ is -N(CH3)-pyridin-2-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 535

Compounds of the formula la.13 in which R ⁶ is -NH-pyrimidin-2-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 536

Compounds of the formula la.13 in which R ⁶ is -NH-pyrimidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 537

Compounds of the formula la.13 in which R ⁶ is -NH-pyrimidin-5-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 538

Compounds of the formula la.13 in which R ⁶ is -CH2-COOCH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 539

Compounds of the formula la.13 in which R ⁶ is -CH2-COO-CH2CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 540

Compounds of the formula la.13 in which R ⁶ is -CH2-CONH-CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 541

Compounds of the formula la.13 in which R ⁶ is -CH2-CONH-CH2CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 542

Compounds of the formula la.13 in which R ⁶ is -CH2-CONH-CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 543

Compounds of the formula la.13 in which R ⁶ is -CH2-CONH-CH2CF3 and the combina- tion of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 544

Compounds of the formula la.13 in which R ⁶ is -Chb-CONH-cyclopropyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 545

Compounds of the formula la.13 in which R ⁶ is -Chb-CONH-isopropyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 546

Compounds of the formula la.13 in which R ⁶ is -CH2-CONH-CH(CF ₃ )CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 547

Compounds of the formula la.13 in which R ⁶ is -CH ₂ -CONH-CH(CF ₃ )2 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 548 Compounds of the formula la.13 in which R ⁶ is -CH2-CONH-CH2CH2CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 549

Compounds of the formula la.13 in which R ⁶ is -CH2-CONH-CH2CN and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 550

Compounds of the formula la.13 in which R ⁶ is -CH2-CONH-CH ₂ C≡CH and the combi- nation of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 551

Compounds of the formula la.13 in which R ⁶ is -CH2-CON(CH ₃ )-CH2CF ₃ and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 552

Compounds of the formula la.13 in which R ⁶ is -CH(CH ₃ )-CONH-CH2CF ₃ and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 553

Compounds of the formula la.13 in which R ⁶ is -Chb-CONH-Chb-cyclopropyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 554

Compounds of the formula la.13 in which R ⁶ is -CH2-CONH-thietan-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 555

Compounds of the formula la.13 in which R ⁶ is -CH2-CONH-1 -oxo-thietan-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 556

Compounds of the formula la.13 in which R ⁶ is -CH2-CONH-1 ,1 -dioxo-thietan-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 557

Compounds of the formula la.13 in which R ⁶ is benzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 558 Compounds of the formula la.13 in which R ⁶ is 2-fluorobenzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 559

Compounds of the formula la.13 in which R ⁶ is 3-fluorobenzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 560

Compounds of the formula la.13 in which R ⁶ is 4-fluorobenzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 561

Compounds of the formula la.13 in which R ⁶ is 2-chlorobenzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 562

Compounds of the formula la.13 in which R ⁶ is 3-chlorobenzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 563

Compounds of the formula la.13 in which R ⁶ is 4-chlorobenzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 564

Compounds of the formula la.13 in which R ⁶ is 2-methoxybenzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 565

Compounds of the formula la.13 in which R ⁶ is 3-methoxybenzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 566

Compounds of the formula la.13 in which R ⁶ is 4-methoxybenzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 567

Compounds of the formula la.13 in which R ⁶ is 2-methylsulfanylbenzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 568

Compounds of the formula la.13 in which R ⁶ is 3-methylsulfanylbenzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 569

Compounds of the formula la.13 in which R ⁶ is 4-methylsulfanylbenzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 570 Compounds of the formula la.13 in which R ⁶ is 2-methylsulfonylbenzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 571

Compounds of the formula la.13 in which R ⁶ is 3-methylsulfonylbenzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 572

Compounds of the formula la.13 in which R ⁶ is 4-methylsulfonylbenzyl and the combi- nation of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 573

Compounds of the formula la.13 in which R ⁶ is pyridin-2-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 574

Compounds of the formula la.13 in which R ⁶ is pyridin-3-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 575

Compounds of the formula la.13 in which R ⁶ is 6-chloro-pyridin-3-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 576

Compounds of the formula la.13 in which R ⁶ is pyridin-4-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 577

Compounds of the formula la.13 in which R ⁶ is 5-chloro-pyridin-2-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 578

Compounds of the formula la.13 in which R ⁶ is 6-(trifluoromethyl)-pyridin-2-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 579

Compounds of the formula la.13 in which R ⁶ is 6-(trifluoromethyl)-pyridin-3-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 580 Compounds of the formula la.13 in which R ⁶ is pyrimidin-2-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 581

Compounds of the formula la.13 in which R ⁶ is pyrimidin-4-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 582

Compounds of the formula la.13 in which R ⁶ is pyrimidin-5-yl-methyl and the combina- tion of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 583

Compounds of the formula la.13 in which R ⁶ is pyridazin-3-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 584

Compounds of the formula la.13 in which R ⁶ is pyrazin-2-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 585

Compounds of the formula la.13 in which R ⁶ is thien-2-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 586

Compounds of the formula la.13 in which R ⁶ is thien-3-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 587

Compounds of the formula la.13 in which R ⁶ is thiazol-2-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 588

Compounds of the formula la.13 in which R ⁶ is thiazol-4-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 589

Compounds of the formula la.13 in which R ⁶ is thiazol-5-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 590

Compounds of the formula la.13 in which R ⁶ is 2-chloro-thiazol-5-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 591 Compounds of the formula la.13 in which R ⁶ is isothiazol-3-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 592

Compounds of the formula la.13 in which R ⁶ is isothiazol-4-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 593

Compounds of the formula la.13 in which R ⁶ is isothiazol-5-yl-methyl and the combina- tion of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 594

Compounds of the formula la.13 in which R ⁶ is oxazol-2-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 595

Compounds of the formula la.13 in which R ⁶ is oxazol-4-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 596

Compounds of the formula la.13 in which R ⁶ is oxazol-5-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 597

Compounds of the formula la.13 in which R ⁶ is isoxazol-3-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 598

Compounds of the formula la.13 in which R ⁶ is isoxazol-4-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 599

Compounds of the formula la.13 in which R ⁶ is isoxazol-5-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 600

Compounds of the formula la.13 in which R ⁶ is [1 ,2,3]-thiadiazol-4-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 601 Compounds of the formula la.13 in which R ⁶ is [1 ,3,4]-thiadiazol-2-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 602

Compounds of the formula la.13 in which R ⁶ is 1 -methyl-imidazol-2-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 603

Compounds of the formula la.13 in which R ⁶ is 1 -methyl-imidazol-4-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 604

Compounds of the formula la.13 in which R ⁶ is 1 -methyl-imidazol-5-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 605

Compounds of the formula la.13 in which R ⁶ is 1 -methyl-pyrazol-3-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 606

Compounds of the formula la.13 in which R ⁶ is 2-methyl-pyrazol-3-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 607

Compounds of the formula la.13 in which R ⁶ is tetrahydrofuran-3-yl-methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 608

Compounds of the formula la.13 in which R ⁶ is 1 ,3-dioxolan-2-yl-methyl and the combi- nation of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 609

Compounds of the formula la.13 in which R ⁶ is 2-pyridyl-eth-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 610

Compounds of the formula la.13 in which R ⁶ is (1 R)-2-pyridyl-eth-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 61 1 Compounds of the formula la.13 in which R ⁶ is (1 S)-2-pyridyl-eth-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 612

Compounds of the formula la.13 in which R ⁶ is -CONH2 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 613

Compounds of the formula la.13 in which R ⁶ is -CONH-CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 614

Compounds of the formula la.13 in which R ⁶ is -CONH-CH2CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 615

Compounds of the formula la.13 in which R ⁶ is -CONH-CH2CH2CH3 and the combina- tion of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 616

Compounds of the formula la.13 in which R ⁶ is -CONH-cyclopropyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 617

Compounds of the formula la.13 in which R ⁶ is -CONH-Chb-cyclopropyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 618

Compounds of the formula la.13 in which R ⁶ is -CONH-phenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 619

Compounds of the formula la.13 in which R ⁶ is -CONH-benzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 620

Compounds of the formula la.13 in which R ⁶ is -NHCO-NH-CH2CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 621

Compounds of the formula la.13 in which R ⁶ is -NHCO-NH-CH2CHF2 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 622 Compounds of the formula la.13 in which R ⁶ is -CH=NOCH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 623

Compounds of the formula la.13 in which R ⁶ is -CH=NOCH2CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 624

Compounds of the formula la.13 in which R ⁶ is 3-oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 625

Compounds of the formula la.13 in which R ⁶ is 2-methyl-3-oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 626

Compounds of the formula la.13 in which R ⁶ is 2-ethyl-3-oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 627

Compounds of the formula la.13 in which R ⁶ is 2-propyl-3-oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 628

Compounds of the formula la.13 in which R ⁶ is 2-butyl-3-oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 629

Compounds of the formula la.13 in which R ⁶ is 2-(but-2-yl)-3-oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 630

Compounds of the formula la.13 in which R ⁶ is 2-(3-bromopropyl)-3-oxo-isoxazolidin-4- yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 631

Compounds of the formula la.13 in which R ⁶ is 2-(2-fluoroethyl)-3-oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 632 Compounds of the formula la.13 in which R ⁶ is 2-(2,2-difluoroethyl)-3-oxo-isoxazolidin- 4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 633

Compounds of the formula la.13 in which R ⁶ is 2-(2,2,2-trifluoroethyl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 634

Compounds of the formula la.13 in which R ⁶ is 2-(3,3,3-trifluoropropyl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 635

Compounds of the formula la.13 in which R ⁶ is 2-(2-methoxyethyl)-3-oxo-isoxazolidin- 4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 636

Compounds of the formula la.13 in which R ⁶ is 2-(1 -methoxy-prop-2-yl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 637

Compounds of the formula la.13 in which R ⁶ is 2-cyclobutyl-3-oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 638

Compounds of the formula la.13 in which R ⁶ is 2-(2-methylcyclohex-1 -yl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 639

Compounds of the formula la.13 in which R ⁶ is 2-(phenylmethyl)-3-oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 640

Compounds of the formula la.13 in which R ⁶ is 2-(1 -phenyl-eth-1 -yl)-3-oxo-isoxaolidin- 4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 641

Compounds of the formula la.13 in which R ⁶ is 2-(2-phenyl-eth-1 -yl)-3-oxo-isoxazolidin- 4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 642

Compounds of the formula la.13 in which R ⁶ is 2-[(3-chlorophenyl)-methyl]-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 643

Compounds of the formula la.13 in which R ⁶ is 2-[(2-fluorophenyl)-methyl]-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 644

Compounds of the formula la.13 in which R ⁶ is 2-[(4-methoxyphenyl)-methyl]-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 645

Compounds of the formula la.13 in which R ⁶ is 2-[(2-trifluoromethylphenyl)-methyl]-3- oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 646

Compounds of the formula la.13 in which R ⁶ is 2-[(2-trifluoromethoxyphenyl)-methyl]-3- oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound cor- responds in each case to one row of Table A

Table 647

Compounds of the formula la.13 in which R ⁶ is 2-(pyridin-2-yl-methyl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 648

Compounds of the formula la.13 in which R ⁶ is 2-(pyridin-3-yl-methyl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 649

Compounds of the formula la.13 in which R ⁶ is 2-[(2-chloropyridin-5-yl)-methyl]-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 650

Compounds of the formula la.13 in which R ⁶ is 2-[(1 -methyl-1 H-imidazol-4-yl)-methyl]- 3-oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 651 Compounds of the formula la.13 in which R ⁶ is 2-[(furan-2-yl)-methyl]-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 652

Compounds of the formula la.13 in which R ⁶ is 2-[(2-thiophen-2'-yl)-eth-1 -yl]-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 653

Compounds of the formula la.13 in which R ⁶ is 2-[2-(indol-3'-yl)-eth-1 -yl]-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 654

Compounds of the formula la.13 in which R ⁶ is 2-[(1 H-benzimidazol-2-yl)-methyl]-3- oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound cor- responds in each case to one row of Table A

Table 655

Compounds of the formula la.13 in which R ⁶ is 2-[(oxetan-2-yl)-methyl]-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 656

Compounds of the formula la.13 in which R ⁶ is 2-[(tetrahydrofuran-2-yl)-methyl]-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 657

Compounds of the formula la.13 in which R ⁶ is 2-[(2-[1 ',3']dioxolan-2'-yl)-eth-1 -yl]-3- oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 658

Compounds of the formula la.13 in which R ⁶ is 2-[(2-morpholin-4'-yl)-eth-1 yl]-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 659

Compounds of the formula la.13 in which R ⁶ is 2-[(2-benzo[1 ',3']dioxol-5'-yl)-eth-1 -yl]-3- oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound cor- responds in each case to one row of Table A

Table 660

Compounds of the formula la.13 in which R ⁶ is 2-[(2,3-dihydro-benzo[1 ,4]dioxin-6-yl)- methyl]-3-oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 661

Compounds of the formula la.13 in which R ⁶ is 2-(2-chlorophenyl)-3-oxo-isoxazolidin-4- yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 662

Compounds of the formula la.13 in which R ⁶ is 2-(3-fluorophenyl)-3-oxo-isoxazolidin-4- yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 663

Compounds of the formula la.13 in which R ⁶ is 2-(2-methylphenyl)-3-oxo-isoxazolidin- 4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 664

Compounds of the formula la.13 in which R ⁶ is 2-(2-chloro-6-methylphenyl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 665

Compounds of the formula la.13 in which R ⁶ is 2-(2-trifluoromethylphenyl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corre- sponds in each case to one row of Table A

Table 666

Compounds of the formula la.13 in which R ⁶ is 2-(2,4-dimethoxyphenyl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 667

Compounds of the formula la.13 in which R ⁶ is 2-(3-methylpyrid-2-yl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 668

Compounds of the formula la.13 in which R ⁶ is 2-(1 ,3-dimethyl-1 H-pyrazol-5-yl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 669

Compounds of the formula la.13 in which R ⁶ is 2-(4-methylthiazol-2-yl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 670 Compounds of the formula la.13 in which R ⁶ is 2-(5-methylthiadiazol-2-yl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 671

Compounds of the formula la.13 in which R ⁶ is 2-(quinolin-2-yl)-3-oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 672

Compounds of the formula la.13 in which R ⁶ is 2-(quinolin-5-yl)-3-oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 673

Compounds of the formula la.13 in which R ⁶ is 2-(benzothiazol-6-yl)-3-oxo-isoxazolidin- 4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 674

Compounds of the formula la.13 in which R ⁶ is 2-(4-methylbenzothiazol-2-yl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 675

Compounds of the formula la.13 in which R ⁶ is 2-(thietan-3-yl)-3-oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 676

Compounds of the formula la.13 in which R ⁶ is 2-(1 -oxo-thietan-3-yl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 677

Compounds of the formula la.13 in which R ⁶ is 2-(1 ,1 -dioxo-thietan-3-yl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 678

Compounds of the formula la.13 in which R ⁶ is 2-(3-methylthietan-3-yl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corre- sponds in each case to one row of Table A

Table 679

Compounds of the formula la.13 in which R ⁶ is 2-(oxetan-3-yl)-3-oxo-isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 680

Compounds of the formula la.13 in which R ⁶ is 2-(tetrahydropyran-4-yl)-3-oxo- isoxazolidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 681 to 920

Compounds of the formula la.14 in which R ⁶ is as defined in any of tables 441 to 680 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 921 to 1 160

Compounds of the formula la.15 in which R ⁶ is as defined in any of tables 441 to 680 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 1 161 to 1400

Compounds of the formula la.16 in which R ⁶ is as defined in any of tables 441 to 680 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 1401

Compounds of the formula la.17 in which R ⁸ is methyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 1402

Compounds of the formula la.17 in which R ⁸ is ethyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 1403

Compounds of the formula la.17 in which R ⁸ is propyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 1404

Compounds of the formula la.17 in which R ⁸ is isopropyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1405

Compounds of the formula la.17 in which R ⁸ is n-butyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 1406

Compounds of the formula la.17 in which R ⁸ is sec-butyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1407

Compounds of the formula la.17 in which R ⁸ is isobutyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 1408 Compounds of the formula la.17 in which R ⁸ is tert-butyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1409

Compounds of the formula la.17 in which R ⁸ is CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 1410

Compounds of the formula la.17 in which R ⁸ is CH2CHF2 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 141 1

Compounds of the formula la.17 in which R ⁸ is CH2CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1412

Compounds of the formula la.17 in which R ⁸ is CH2CH2CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1413

Compounds of the formula la.17 in which R ⁸ is cyclopropyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1414

Compounds of the formula la.17 in which R ⁸ is methylthiomethyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1415

Compounds of the formula la.17 in which R ⁸ is ethylthiomethyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1416

Compounds of the formula la.17 in which R ⁸ is methylsulfinylmethyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 1417

Compounds of the formula la.17 in which R ⁸ is ethylsulfinylmethyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1418

Compounds of the formula la.17 in which R ⁸ is methylsulfonylmethyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 1419

Compounds of the formula la.17 in which R ⁸ is ethylsulfonylmethyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1420 Compounds of the formula la.17 in which R ⁸ is phenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 1421

Compounds of the formula la.17 in which R ⁸ is 2-fluorophenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1422

Compounds of the formula la.17 in which R ⁸ is 3-fluorophenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1423

Compounds of the formula la.17 in which R ⁸ is 4-fluorophenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1424

Compounds of the formula la.17 in which R ⁸ is 2,3-difluorophenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1425

Compounds of the formula la.17 in which R ⁸ is 2,4-difluorophenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1426

Compounds of the formula la.17 in which R ⁸ is 2,5-difluorophenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1427

Compounds of the formula la.17 in which R ⁸ is 2,6-difluorophenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1428

Compounds of the formula la.17 in which R ⁸ is 3,4-difluorophenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1429

Compounds of the formula la.17 in which R ⁸ is 3,5-difluorophenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1430

Compounds of the formula la.17 in which R ⁸ is 2-chlorophenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1431

Compounds of the formula la.17 in which R ⁸ is 3-chlorophenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1432

Compounds of the formula la.17 in which R ⁸ is 4-chlorophenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1433 Compounds of the formula la.17 in which R ⁸ is 2-methoxyphenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1434

Compounds of the formula la.17 in which R ⁸ is 3-methoxyphenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1435

Compounds of the formula la.17 in which R ⁸ is 4-methoxyphenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1436

Compounds of the formula la.17 in which R ⁸ is thietan-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1437

Compounds of the formula la.17 in which R ⁸ is 1 -oxo-thietan-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1438

Compounds of the formula la.17 in which R ⁸ is 1 ,1-dioxo-thietan-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 1439

Compounds of the formula la.17 in which R ⁸ is pyridin-2-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1440

Compounds of the formula la.17 in which R ⁸ is pyridin-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1441

Compounds of the formula la.17 in which R ⁸ is pyridin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1442

Compounds of the formula la.17 in which R ⁸ is 4-chloropyridin-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1443

Compounds of the formula la.17 in which R ⁸ is -NH-CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1444

Compounds of the formula la.17 in which R ⁸ is -NH-CH2CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1445

Compounds of the formula la.17 in which R ⁸ is -NH-CH2CH2CH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1446

Compounds of the formula la.17 in which R ⁸ is -NH-CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1447

Compounds of the formula la.17 in which R ⁸ is -NH-CH2CHF2 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1448

Compounds of the formula la.17 in which R ⁸ is -NH-CH2CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1449

Compounds of the formula la.17 in which R ⁸ is -NH-phenyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 1450

Compounds of the formula la.17 in which R ⁸ is -NH-benzyl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Tables 1451 to 1500

Compounds of the formula la.18 in which R ⁸ is as defined in any of tables 1401 to 1450 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 1501 to 1550

Compounds of the formula la.19 in which R ⁸ is as defined in any of tables 1401 to 1450 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 1551 to 1600

Compounds of the formula la.20 in which R ⁸ is as defined in any of tables 1401 to 1450 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 1601 to 1650

Compounds of the formula la.21 in which R ⁸ is as defined in any of tables 1401 to 1450 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 1651 to 1700

Compounds of the formula la.22 in which R ⁸ is as defined in any of tables 1401 to 1450 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 1701 to 1750

Compounds of the formula la.23 in which R ⁸ is as defined in any of tables1401 to 1450 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Tables 1751 to 1800

Compounds of the formula la.24 in which R ⁸ is as defined in any of tables 1401 to 1450 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 1801 to 1850

Compounds of the formula la.25 in which R ⁸ is as defined in any of tables 1401 to 1450 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 1851 to 1900

Compounds of the formula la.26 in which R ⁸ is as defined in any of tables 1401 to 1450 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 1901 to 1950

Compounds of the formula la.27 in which R ⁸ is as defined in any of tables 1401 to 1450 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Tables 1951 to 2000

Compounds of the formula la.28 in which R ⁸ is as defined in any of tables 1401 to 1450 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2001

Compounds of the formula la.29 in which A ⁴ is 1 H-pyrrol-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2002

Compounds of the formula la.29 in which A ⁴ is 1 H-3-chloro-pyrrol-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2003

Compounds of the formula la.29 in which A ⁴ is 1 H-3-cyano-pyrrol-1 -yl and the combi- nation of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2004

Compounds of the formula la.29 in which A ⁴ is 1 H-pyrazol-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2005

Compounds of the formula la.29 in which A ⁴ is 1 H-4-cloro-pyrazol-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2006 Compounds of the formula la.29 in which A ⁴ is 1 H-4-cyano-pyrazol-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2007

Compounds of the formula la.29 in which A ⁴ is 1 H-imidazol-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2008

Compounds of the formula la.29 in which A ⁴ is 1 H-4-chloro-imidazol-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2009

Compounds of the formula la.29 in which A ⁴ is 1 H-4-cyano-imidazol-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2010

Compounds of the formula la.29 in which A ⁴ is 1 H-[1 ,2,4]-triazol-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 201 1

Compounds of the formula la.29 in which A ⁴ is 1 H-[1 ,2,4]-3-chloro-triazol-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2012

Compounds of the formula la.29 in which A ⁴ is 1 H-[1 ,2,4]-3-cyano-triazol-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2013

Compounds of the formula la.29 in which A ⁴ is 1 H-1 -methyl-pyrrol-2-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2014

Compounds of the formula la.29 in which A ⁴ is 1 H-1 -methyl-pyrrol-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2015

Compounds of the formula la.29 in which A ⁴ is 1 H-1 -methyl-pyrazol-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2016 Compounds of the formula la.29 in which A ⁴ is 1 H-1 -methyl-pyrazol-5-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2017

Compounds of the formula la.29 in which A ⁴ is 1 H-1 ,3-dimethyl-pyrazol-5-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2018

Compounds of the formula la.29 in which A ⁴ is 1 H-1 -methyl-3-trifluoromethyl-pyrazol-5- yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2019

Compounds of the formula la.29 in which A ⁴ is 1 H-1 -[1 ,2,3]-triazol-5-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2020

Compounds of the formula la.29 in which A ⁴ is pyridin-2-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2021

Compounds of the formula la.29 in which A ⁴ is pyridin-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2022

Compounds of the formula la.29 in which A ⁴ is pyridin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2023

Compounds of the formula la.29 in which A ⁴ is pyrimidin-2-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2024

Compounds of the formula la.29 in which A ⁴ is pyrimidin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2025

Compounds of the formula la.29 in which A ⁴ is pyrimidin-5-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2026

Compounds of the formula la.29 in which A ⁴ is pyrazin-2-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Tables 2027 to 2052 Compounds of the formula la.30 in which A ⁴ is as defined in any of tables 2001 to 2026 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2053

Compounds of the formula la.31 in which Y is H and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2054

Compounds of the formula la.31 in which Y is OH and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2055

Compounds of the formula la.31 in which Y is OCH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2056

Compounds of the formula la.31 in which Y is OC2H5 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2057

Compounds of the formula la.31 in which Y is OC(CH3)3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2058

Compounds of the formula la.31 in which Y is OCH2CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2059

Compounds of the formula la.31 in which Y is OCH2CH2CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2060

Compounds of the formula la.31 in which Y is OCH2-(pyridine-2-yl) and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2061

Compounds of the formula la.31 in which Y is aziridin-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2062

Compounds of the formula la.31 in which Y is azetidin-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2063

Compounds of the formula la.31 in which Y is pyrrolidin-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2064 Compounds of the formula la.31 in which Y is piperidin-1 -yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2065

Compounds of the formula la.31 in which Y is morpholin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2066

Compounds of the formula la.31 in which Y is thiomorpholin-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2067

Compounds of the formula la.31 in which Y is thiazinan-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2068

Compounds of the formula la.31 in which Y is 1 -oxo-thiazinan-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2069

Compounds of the formula la.31 in which Y is 1 ,1 -dioxo-thiazinan-4-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2070

Compounds of the formula la.31 in which Y is thiazolidin-3-yl and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2071

Compounds of the formula la.31 in which Y is -N=S(CH3)2 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2072

Compounds of the formula la.31 in which Y is -N=S(C2H ₅ )2 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2073

Compounds of the formula la.31 in which Y is -N=S[CH(CH3)2]2 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A Table 2074

Compounds of the formula la.31 in which Y is -N(CH3)-CH2-(thiazol-4-yl) and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2075

Compounds of the formula la.31 in which Y is -N(C2H ₅ )-CH2-(thiazol-4-yl) and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2076 Compounds of the formula la.31 in which Y is -N(CH3)-CH2-(pyridin-2-yl) and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2077

Compounds of the formula la.31 in which Y is -N(C2H ₅ )-CH2-(pyridin-2-yl) and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2078

Compounds of the formula la.31 in which Y is -N(CH2CN)-CH2-(pyridin-2-yl) and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2079

Compounds of the formula la.31 in which Y is -N(CH2-C≡CH)-CH2-(pyridin-2-yl) and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2080

Compounds of the formula la.31 in which Y is -N(CH3)-CH2-CONH-CH ₂ CF3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2081

Compounds of the formula la.31 in which Y is -N^Hsj-Ch -CONH-CI-bCFs and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table 2082

Compounds of the formula la.31 in which Y is -N(CH3)-OCH3 and the combination of R ^2a , R ^2b , R ^2c and R ⁴ for a compound corresponds in each case to one row of Table A

Table A

No. _R 2a _R 2b _R 2c R ⁴

A-1 F H F H

A-2 F F F H

A-3 F CI F H

A-4 F Br F H

A-5 F H CI H

A-6 F H Br H

A-7 CI H CI H

A-8 CI CI CI H

A-9 CI F CI H _R 2a _R 2b _R 2c R ⁴

A-10 CI Br CI H

A-1 1 CI H Br H

A-12 Br H Br H

A-13 Br F Br H

A-14 Br CI Br H

A-15 CFs H F H

A-16 CFs H CI H

A-17 CFs H Br H

A-18 CFs H CFs H

A-19 CFs F F H

A-20 CFs CI CI H

A-21 CFs Br Br H

A-22 SF ₅ H F H

A-23 SF ₅ H CI H

A-24 SF ₅ H Br H

A-25 SF ₅ H CFs H

A-26 F H F CHs

A-27 F F F CHs

A-28 F CI F CHs

A-29 F Br F CHs

A-30 F H CI CHs

A-31 F H Br CHs

A-32 CI H CI CHs

A-33 CI CI CI CHs

A-34 CI F CI CHs

A-35 CI Br CI CHs

A-36 CI H Br CHs

A-37 Br H Br CHs

A-38 Br F Br CHs

A-39 Br CI Br CHs

A-40 CFs H F CHs

A-41 CFs H CI CHs

A-42 CFs H Br CHs

A-43 CFs H CFs CHs

A-44 CFs F F CHs

A-45 CFs CI CI CHs

A-46 CFs Br Br CHs _R 2a _R 2b _R 2c R ⁴

A-84 CI F CI CH(CHs) ₂

A-85 CI Br CI CH(CHs) ₂

A-86 CI H Br CH(CHs) ₂

A-87 Br H Br CH(CHs) ₂

A-88 Br F Br CH(CHs) ₂

A-89 Br CI Br CH(CHs) ₂

A-90 CFs H F CH(CHs) ₂

A-91 CFs H CI CH(CHs) ₂

A-92 CFs H Br CH(CHs) ₂

A-93 CFs H CFs CH(CHs) ₂

A-94 CFs F F CH(CHs) ₂

A-95 CFs CI CI CH(CHs) ₂

A-96 CFs Br Br CH(CHs) ₂

A-97 SF ₅ H F CH(CHs) ₂

A-98 SF ₅ H CI CH(CHs) ₂

A-99 SF ₅ H Br CH(CHs) ₂

A-100 SF ₅ H CFs CH(CHs) ₂

A-101 F H F CHF ₂

A-102 F F F CHF ₂

A-103 F CI F CHF ₂

A-104 F Br F CHF ₂

A-105 F H CI CHF ₂

A-106 F H Br CHF ₂

A-107 CI H CI CHF ₂

A-108 CI CI CI CHF ₂

A-109 CI F CI CHF ₂

A-1 10 CI Br CI CHF ₂

A-1 1 1 CI H Br CHF ₂

A-1 12 Br H Br CHF ₂

A-1 13 Br F Br CHF ₂

A-1 14 Br CI Br CHF ₂

A-1 15 CFs H F CHF ₂

A-1 16 CFs H CI CHF ₂

A-1 17 CFs H Br CHF ₂

A-1 18 CFs H CFs CHF ₂

A-1 19 CFs F F CHF ₂

A-120 CFs CI CI CHF _{2 R} 2a _R 2b _R 2c R ⁴

A-121 CFs Br Br CHF ₂

A-122 SF ₅ H F CHF ₂

A-123 SF ₅ H CI CHF ₂

A-124 SF ₅ H Br CHF ₂

A-125 SF ₅ H CFs CHF ₂

A-126 F H F CFs

A-127 F F F CFs

A-128 F CI F CFs

A-129 F Br F CFs

A-130 F H CI CFs

A-131 F H Br CFs

A-132 CI H CI CFs

A-133 CI CI CI CFs

A-134 CI F CI CFs

A-135 CI Br CI CFs

A-136 CI H Br CFs

A-137 Br H Br CFs

A-138 Br F Br CFs

A-139 Br CI Br CFs

A-140 CFs H F CFs

A-141 CFs H CI CFs

A-142 CFs H Br CFs

A-143 CFs H CFs CFs

A-144 CFs F F CFs

A-145 CFs CI CI CFs

A-146 CFs Br Br CFs

A-147 SF ₅ H F CFs

A-148 SF ₅ H CI CFs

A-149 SF ₅ H Br CFs

A-150 SFs H CFs CFs

A-151 F H F CH ₂ -CH=CH ₂

A-152 F F F CH ₂ -CH=CH ₂

A-153 F CI F CH ₂ -CH=CH ₂

A-154 F Br F CH ₂ -CH=CH ₂

A-155 F H CI CH ₂ -CH=CH ₂

A-156 F H Br CH ₂ -CH=CH ₂

A-157 CI H CI CH ₂ -CH=CH ₂

611

6££9/.0/ZlOZd3/I3d £t6Z60/£ioz OAV _R 2a _R 2b _R 2c R ⁴

A-195 CFs CI CI CH=CH ₂

A-196 CFs Br Br CH=CH ₂

A-197 SF ₅ H F CH=CH ₂

A-198 SF ₅ H CI CH=CH ₂

A-199 SF ₅ H Br CH=CH ₂

A-200 SF ₅ H CFs CH=CH ₂

A-201 F H F C≡CH

A-202 F F F C≡CH

A-203 F CI F C≡CH

A-204 F Br F C≡CH

A-205 F H CI C≡CH

A-206 F H Br C≡CH

A-207 CI H CI C≡CH

A-208 CI CI CI C≡CH

A-209 CI F CI C≡CH

A-210 CI Br CI C≡CH

A-21 1 CI H Br C≡CH

A-212 Br H Br C≡CH

A-213 Br F Br C≡CH

A-214 Br CI Br C≡CH

A-215 CFs H F C≡CH

A-216 CFs H CI C≡CH

A-217 CFs H Br C≡CH

A-218 CFs H CFs C≡CH

A-219 CFs F F C≡CH

A-220 CFs CI CI C≡CH

A-221 CFs Br Br C≡CH

A-222 SF ₅ H F C≡CH

A-223 SF ₅ H CI C≡CH

A-224 SF ₅ H Br C≡CH

A-225 SF ₅ H CFs C≡CH

A-226 F H F ^c CsH ₅ ^*

A-227 F F F ^c CsH ₅ ^*

A-228 F CI F ^c CsH ₅ ^*

A-229 F Br F ^c CsH ₅ ^*

A-230 F H CI ^c CsH ₅ ^*

A-231 F H Br ^c CsH ₅ ^* _R 2a _R 2b _R 2c R ⁴

A-232 CI H CI ^c CsH ₅ ^*

A-233 CI CI CI ^c CsH ₅ ^*

A-234 CI F CI ^c CsH ₅ ^*

A-235 CI Br CI ^c CsH ₅ ^*

A-236 CI H Br ^c CsH ₅ ^*

A-237 Br H Br ^c CsH ₅ ^*

A-238 Br F Br ^c CsH ₅ ^*

A-239 Br CI Br ^c CsH ₅ ^*

A-240 CFs H F ^c CsH ₅ ^*

A-241 CFs H CI ^c CsH ₅ ^*

A-242 CFs H Br ^c CsH ₅ ^*

A-243 CFs H CFs ^c CsH ₅ ^*

A-244 CFs F F ^c CsH ₅ ^*

A-245 CFs CI CI ^c CsH ₅ ^*

A-246 CFs Br Br ^c CsH ₅ ^*

A-247 SF ₅ H F ^c CsH ₅ ^*

A-248 SF ₅ H CI ^c CsH ₅ ^*

A-249 SF ₅ H Br ^c CsH ₅ ^*

A-250 SF ₅ H CFs ^c CsH ₅ ^*

A-251 F H F F

A-252 F F F F

A-253 F CI F F

A-254 F Br F F

A-255 F H CI F

A-256 F H Br F

A-257 CI H CI F

A-258 CI CI CI F

A-259 CI F CI F

A-260 CI Br CI F

A-261 CI H Br F

A-262 Br H Br F

A-263 Br F Br F

A-264 Br CI Br F

A-265 CFs H F F

A-266 CFs H CI F

A-267 CFs H Br F

A-268 CFs H CFs F _R 2a _R 2b _R 2c R ⁴

A-269 CFs F F F

A-270 CFs CI CI F

A-271 CFs Br Br F

A-272 SF ₅ H F F

A-273 SF ₅ H CI F

A-274 SF ₅ H Br F

A-275 SF ₅ H CFs F

A-276 F H F CI

A-277 F F F CI

A-278 F CI F CI

A-279 F Br F CI

A-280 F H CI CI

A-281 F H Br CI

A-282 CI H CI CI

A-283 CI CI CI CI

A-284 CI F CI CI

A-285 CI Br CI CI

A-286 CI H Br CI

A-287 Br H Br CI

A-288 Br F Br CI

A-289 Br CI Br CI

A-290 CFs H F CI

A-291 CFs H CI CI

A-292 CFs H Br CI

A-293 CFs H CFs CI

A-294 CFs F F CI

A-295 CFs CI CI CI

A-296 CFs Br Br CI

A-297 SF ₅ H F CI

A-298 SF ₅ H CI CI

A-299 SF ₅ H Br CI

A-300 SF ₅ H CFs CI

A-301 F H F Br

A-302 F F F Br

A-303 F CI F Br

A-304 F Br F Br

A-305 F H CI Br _R 2a _R 2b _R 2c R ⁴

A-306 F H Br Br

A-307 CI H CI Br

A-308 CI CI CI Br

A-309 CI F CI Br

A-310 CI Br CI Br

A-31 1 CI H Br Br

A-312 Br H Br Br

A-313 Br F Br Br

A-314 Br CI Br Br

A-315 CFs H F Br

A-316 CFs H CI Br

A-317 CFs H Br Br

A-318 CFs H CFs Br

A-319 CFs F F Br

A-320 CFs CI CI Br

A-321 CFs Br Br Br

A-322 SF ₅ H F Br

A-323 SF ₅ H CI Br

A-324 SF ₅ H Br Br

A-325 SF ₅ H CFs Br

A-326 F H F CN

A-327 F F F CN

A-328 F CI F CN

A-329 F Br F CN

A-330 F H CI CN

A-331 F H Br CN

A-332 CI H CI CN

A-333 CI CI CI CN

A-334 CI F CI CN

A-335 CI Br CI CN

A-336 CI H Br CN

A-337 Br H Br CN

A-338 Br F Br CN

A-339 Br CI Br CN

A-340 CFs H F CN

A-341 CFs H CI CN

A-342 CFs H Br CN _R 2a _R 2b _R 2c R ⁴

A-417 CFs H Br OCH(CHs) ₂

A-418 CFs H CFs OCH(CHs) ₂

A-419 CFs F F OCH(CHs) ₂

A-420 CFs CI CI OCH(CHs) ₂

A-421 CFs Br Br OCH(CHs) ₂

A-422 SF ₅ H F OCH(CHs) ₂

A-423 SF ₅ H CI OCH(CHs) ₂

A-424 SF ₅ H Br OCH(CHs) ₂

A-425 SF ₅ H CFs OCH(CHs) ₂

A-426 F H F OCH ₂ CH=CH ₂

A-427 F F F OCH ₂ CH=CH ₂

A-428 F CI F OCH ₂ CH=CH ₂

A-429 F Br F OCH ₂ CH=CH ₂

A-430 F H CI OCH ₂ CH=CH ₂

A-431 F H Br OCH ₂ CH=CH ₂

A-432 CI H CI OCH ₂ CH=CH ₂

A-433 CI CI CI OCH ₂ CH=CH ₂

A-434 CI F CI OCH ₂ CH=CH ₂

A-435 CI Br CI OCH ₂ CH=CH ₂

A-436 CI H Br OCH ₂ CH=CH ₂

A-437 Br H Br OCH ₂ CH=CH ₂

A-438 Br F Br OCH ₂ CH=CH ₂

A-439 Br CI Br OCH ₂ CH=CH ₂

A-440 CFs H F OCH ₂ CH=CH ₂

A-441 CFs H CI OCH ₂ CH=CH ₂

A-442 CFs H Br OCH ₂ CH=CH ₂

A-443 CFs H CFs OCH ₂ CH=CH ₂

A-444 CFs F F OCH ₂ CH=CH ₂

A-445 CFs CI CI OCH ₂ CH=CH ₂

A-446 CFs Br Br OCH ₂ CH=CH ₂

A-447 SF ₅ H F OCH ₂ CH=CH ₂

A-448 SF ₅ H CI OCH ₂ CH=CH ₂

A-449 SF ₅ H Br OCH ₂ CH=CH ₂

A-450 SF ₅ H CFs OCH ₂ CH=CH ₂

A-451 F H F 0- ^c CsH ₅ ^*

A-452 F F F 0- ^c CsH ₅ ^*

A-453 F CI F 0- ^c CsH ₅ ^* _R 2a _R 2b _R 2c R ⁴

A-602 F F F SCH(CHs) ₂

A-603 F CI F SCH(CHs) ₂

A-604 F Br F SCH(CHs) ₂

A-605 F H CI SCH(CHs) ₂

A-606 F H Br SCH(CHs) ₂

A-607 CI H CI SCH(CHs) ₂

A-608 CI CI CI SCH(CHs) ₂

A-609 CI F CI SCH(CHs) ₂

A-610 CI Br CI SCH(CHs) ₂

A-61 1 CI H Br SCH(CHs) ₂

A-612 Br H Br SCH(CHs) ₂

A-613 Br F Br SCH(CHs) ₂

A-614 Br CI Br SCH(CHs) ₂

A-615 CFs H F SCH(CHs) ₂

A-616 CFs H CI SCH(CHs) ₂

A-617 CFs H Br SCH(CHs) ₂

A-618 CFs H CFs SCH(CHs) ₂

A-619 CFs F F SCH(CHs) ₂

A-620 CFs CI CI SCH(CHs) ₂

A-621 CFs Br Br SCH(CHs) ₂

A-622 SF ₅ H F SCH(CHs) ₂

A-623 SF ₅ H CI SCH(CHs) ₂

A-624 SF ₅ H Br SCH(CHs) ₂

A-625 SF ₅ H CFs SCH(CHs) ₂

A-626 F H F SCH ₂ CH=CH ₂

A-627 F F F SCH ₂ CH=CH ₂

A-628 F CI F SCH ₂ CH=CH ₂

A-629 F Br F SCH ₂ CH=CH ₂

A-630 F H CI SCH ₂ CH=CH ₂

A-631 F H Br SCH ₂ CH=CH ₂

A-632 CI H CI SCH ₂ CH=CH ₂

A-633 CI CI CI SCH ₂ CH=CH ₂

A-634 CI F CI SCH ₂ CH=CH ₂

A-635 CI Br CI SCH ₂ CH=CH ₂

A-636 CI H Br SCH ₂ CH=CH ₂

A-637 Br H Br SCH ₂ CH=CH ₂

A-638 Br F Br SCH ₂ CH=CH _{2 R} 2a _R 2b _R 2c R ⁴

A-639 Br CI Br SCH ₂ CH=CH ₂

A-640 CFs H F SCH ₂ CH=CH ₂

A-641 CFs H CI SCH ₂ CH=CH ₂

A-642 CFs H Br SCH ₂ CH=CH ₂

A-643 CFs H CFs SCH ₂ CH=CH ₂

A-644 CFs F F SCH ₂ CH=CH ₂

A-645 CFs CI CI SCH ₂ CH=CH ₂

A-646 CFs Br Br SCH ₂ CH=CH ₂

A-647 SF ₅ H F SCH ₂ CH=CH ₂

A-648 SF ₅ H CI SCH ₂ CH=CH ₂

A-649 SF ₅ H Br SCH ₂ CH=CH ₂

A-650 SF ₅ H CFs SCH ₂ CH=CH ₂

A-651 F H F S- ^c CsH ₅ ^*

A-652 F F F S- ^c CsH ₅ ^*

A-653 F CI F S- ^c CsH ₅ ^*

A-654 F Br F S- ^c CsH ₅ ^*

A-655 F H CI S- ^c CsH ₅ ^*

A-656 F H Br S- ^c CsH ₅ ^*

A-657 CI H CI S- ^c CsH ₅ ^*

A-658 CI CI CI S- ^c CsH ₅ ^*

A-659 CI F CI S- ^c CsH ₅ ^*

A-660 CI Br CI S- ^c CsH ₅ ^*

A-661 CI H Br S- ^c CsH ₅ ^*

A-662 Br H Br S- ^c CsH ₅ ^*

A-663 Br F Br S- ^c CsH ₅ ^*

A-664 Br CI Br S- ^c CsH ₅ ^*

A-665 CFs H F S- ^c CsH ₅ ^*

A-666 CFs H CI S- ^c CsH ₅ ^*

A-667 CFs H Br S- ^c CsH ₅ ^*

A-668 CFs H CFs S- ^c CsH ₅ ^*

A-669 CFs F F S- ^c CsH ₅ ^*

A-670 CFs CI CI S- ^c CsH ₅ ^*

A-671 CFs Br Br S- ^c CsH ₅ ^*

A-672 SF ₅ H F S- ^c CsH ₅ ^*

A-673 SF ₅ H CI S- ^c CsH ₅ ^*

A-674 SF ₅ H Br S- ^c CsH ₅ ^*

A-675 SF ₅ H CFs S- ^c CsH ₅ ^*

* ^C C3H ₅ = cyclopropyl

Among the above compounds, preference is given to compounds la.1 , la.13, la.17, la.19 and la.20 and especially to la.13.

The compounds of the formula (I) can be prepared by novel methods as described below or and in the synthesis descriptions of the working examples, or by standard methods of organic chemistry, e.g. by the methods described hereinafter or in the synthesis descriptions of the working examples. The substituents, variables and indices are as defined above for formula (I), if not otherwise specified.

The invention relates to a method for preparing compounds of formula I as defined in any of the preceding claims, where however R ^3b is hydrogen, which method comprises dehydrating a compound of formula II

wherein B ¹ , B ² , B ³ , G ¹ , G ² , G ³ , G ⁴ , R ¹ , R ^3a and R ^3b are as defined above and A is A or a precursor of A;

to give a compound Γ

and, if necessary (i.e. if A' is a precursor of A), converting the group A into a group A.

A' as a precursor of A is typically a halogen atom, CN, carboxy, tert-butoxycarbonyl, an acetale group, a protected aldehyde group or -OS02-R ^z1 , where R ^z1 is Ci-C4-alkyl, Ci- C4-haloalkyl or phenyl which may be substituted by 1 , 2 or 3 radicals selected from Ci- C4-alkyl, Ci-C4-haloalkyl Ci-C4-alkoxy or Ci-C4-haloalkoxy. A' as a precursor of A is preferably a halogen atom or -OS02-R ^z1 , where R ^z1 is as defined above, and is more preferably a halogen atom or Otriflate.

Dehydration either occurs spontaneously or with the help of dehydrating agents, such as molecular sieves, acid-washed molecular sieves, magnesium sulfate, sodium sulfate, silica gel, SOC , POC , Burgess reagent, trifluoroacetic anhydride, p-toluene sulfonic acid, anhydrous HCI or sulfuric acid. Preferably, p-toluene sulfonic acid or acid- washed molecular sieves are used. The water formed may alternatively be removed, e.g. by azeotropic distillation, e.g. with benzene/toluene as entrainer, e.g. using a Dean Stark trap.

The compound of formula II, in which R ^3b is hydrogen, is preferably obtained by reacting a compound of formula IV

with an amination agent to give a compound of formula III

which reacts spontaneously to the compound II;

wherein B ¹ , B ² , B ³ , G ¹ , G ² , G ³ , G ⁴ , R ¹ and R ^3a are as defined above and A' is A or a precursor of A.

Depending on the amination agents used, amination can the carried out in a one step reaction, wherein compound IV reacts directly to compound III, or as a two step reaction, wherein the SH group of compound IV is first oxidized to a S-CI group, which then further reacts to a S-Nhb group, thus giving compound III.

Suitable amination agents for the one step reaction are for example HOSA (hydroxyla- mine-O-sulfonic acid), which is generally used in the presence of a base (suitable bases being for example sodium hydrogen phosphate, potassium hydrogen phosphate, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methanolate, triethylamine and the like), 0-(diphenylphosphoryl)hydroxyl amine, , which is generally also used in the presence of a base (suitable bases being for example sodium hydrogen phosphate, potassium hydrogen phosphate, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methanolate, triethylamine and the like), 2,4-dinitrophenylhydroxyl amine, O- mesitylensulfonylhydroxylamine and 2-oxa-1 -azaspiro[2.5]octane, among which HOSA and 0-(diphenylphosphoryl)hydroxyl amine are preferred.

The amination is preferably carried out in a solvent, suitable solvents being for example chlorinated alkanes, such as methylene chloride or chloroform, aromatic solvents, such as benzene, toluene, the xylenes, chlorobenzene or dichlorobenzene, and ethers, such as diethylether, dipropylether, methyl tert-butylether, methyl isobutylether, ethylene- gylcol dimethylether, tetrahydrofuran (THF) or dioxane and the like.

The reaction is suitably carried out low temperature, e.g. at from -100 to 0°C or -78 to 0°C. Generally, the compound IV is dispersed in a solvent and cooled to the desired temperature and the base is added followed by the amination agent, or the amination agent is added followed by the base, or base and amination agent are added simultaneously.

In a preferred embodiment, HOSA is used in combination with an amine base, such as triethylamine. In this case, it is preferred to cool compound IV to -30 to 0°C, preferably - 20 to -10°C, to add the amine base at this temperature and then HOSA and keep the reaction at approximately -10 to 0°C.

In an alternatively preferred embodiment, 0-(diphenylphosphoryl)hydroxyl amine is used in combination with a base, preferably with an inorganic base, such as sodium hydrogen phosphate, potassium hydrogen phosphate, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate and specifically sodium hydrogen phosphate. In this case, it is preferred to cool compound IV to -80 to -30°C, preferably - 80 to -70°C, to add the base at this temperature and then O- (diphenylphosphoryl)hydroxyl amine and keep the reaction at approximately 0°C to room temperature. In the two step reaction, the compound IV is first reacted with a chlorination agent which converts the SH group into an S-CI group. Suitable chlorination agents are for example sulfurylchloride, N-chloro succinimide (NCS), sodium hypochlorite, monochlo- roamine (NH2CI) or chlorine, which is preferably used in the presence of FeC . The chlorination can be carried out in analogy to the method described in Synthesis 1987, 1987, 683-688, Tetrahedron 66(36), 2010, 7279-7287, J. Org. Chem. 59(4), 1994, 914- 921 , J. Org. Chem. 63, 1998, 4878-4888 or J. Chem Soc. 1938, 21 14-21 17.

The chlorination is generally carried out in a solvent. Suitable solvents are for example ethers, such as diethylether, dipropylether, methyl tert-butylether, methyl isobutylether, ethylenegylcol dimethylether, tetrahydrofuran or dioxane.

The reaction temperature can vary over wide ranges and is generally from 0°C to the boiling point of the reaction mixture (if a solvent is used). The chlorinated compound is then reacted without isolation with ammonia or ammonium hydroxide. If anhydrous ammonia is used, the reaction is generally carried out at from -78 to - 33°C. If aqueous ammonia or ammonium hydroxide is used, the reaction can also be carried out at higher temperatures, such as 0 to 25°C. The reaction is generally carried out in a solvent. Suitable solvents are for example the above-listed ethers, among which the water-miscible ethers, such as THF and dioxane, are preferred. In general, the chlorinated compound is dissolved in a solvent to which ammonia or ammonium hydroxide is added. The reaction can be carried out as described, for example, in Synthesis, 1987, 8, 683-688.

The chlorination/amination can also be carried as a one pot reaction. For example, the thiol IV is reacted simultaneously with a chlorinating agent (such as NCS or aqueous sodium hypochlorite) and anhydrous or aqueous ammonia in ethereal solvents (such as THF or Et ₂ 0) or water. Preferred is the reaction with NCS in a mixture of THF and anhydrous liquid ammonia at -33°C. For instance, a solution of the thiol IV in THF is added to a solution of NCS (N-chlorosuccinimide) in THF/liquid ammonia at -78°C. The solution is warmed to -30°C and stirred until the ammonia has evaporated. Alternatively, at 0°C, a solution of the sodium thiolate (NaSR) in water is added to a mixture of aqueous ammonia (25%) and aqueous sodium hypochlorite (1 N). The one pot chlorin- ation/amination reaction can be carried out as described, for example, in Tetrahedron 2010, 66, 7279-7287 or in J. Org. Chem. 1994, 59, 914-921.

Compound III can virtually not be isolated as it generally reacts spontaneously in a ring-closing reaction to compound II.

The compound of formula IV is preferably prepared by reacting a compound of formula

V

wherein B ¹ , B ² , B ³ , G ¹ , G ² , G ³ , G ⁴ , R ¹ and R ^3a are as defined in any of claims 1 to 32 and A' is A or a precursor of A; with a sulfur source.

Suitable sulfur sources are for example H ₂ S, metal hydrogen sulfides, such as NaSH or KSH, metal sulfides, such as Na ₂ S, K ₂ S Li ₂ S, Cu ₂ S, MgS, CaS, CuS, FeS and the like, ammonium sulfide [(NH4) ₂ S], tetraalkylammonium sulfides (R4NSH), such as tetrame- thylammonium sulfide, tetraethylammonium sulfide, tetrapropylammonium sulfide and the like, or bistrimethylsilyl sulfide.

H ₂ S as a sulfur source is generally used in the presence of a base, such as Na ₂ C03, K ₂ C03, Cs ₂ C03, sodium acetate, potassium acetate, cesium acetate, amines, such as diethylamine, dipropylamine, triethylamine, diisopropylethylamine and the like, or basic nitrogen-containing heterocycles, such as pyrrolidine, piperidine, piperazine, pyridine, lutidine and the like. Alternatively, H ₂ S as a sulfur source can be used in the presence of a Lewis acid, such as AICIs or FeCI ₃ .

The reaction of compound V with a sulfur source is generally carried out in a solvent, suitable solvents being for example chlorinated alkanes, such as methylene chloride or chloroform, and aromatic solvents, such as benzene, toluene, the xylenes, chloroben- zene or dichlorobenzene.

The reaction temperature can vary over a wide range, such as -78°C to room temperature.

In general, compound V is dissolved in a solvent, optionally cooled, then the base (if used) and subsequently the sulfur source is added

The compound V can alternatively be reacted with a sulfur source which provides a compound IV which is protected at the thiol group SH by a protective group (S-PG). This is advantageous if compound IV is for example subjected to harsher purification conditions or is derivatized, e.g. for converting the precursor group A' into a group A or for modifying group A at this stage. Moreover, purification of the protected product is easier.

Suitable sulfuration reagents which give such protected thiols are for example thiourea (NH ₂ -C(=S)-NH ₂ ), optionally substituted benzyl thiols, such as benzylthiol, o- or p- methoxy-benzylthiol, o- or p-hydroxybenzylthiol, o- or p-acetoxybenzylthiol, o- or p- nitrobenzylthiol or 2,4,6-trimethylbenzylthiol, pyridin-4-yl-methylthiol, quinolin-2-yl- methylthiol, benzyl metal sulfides, such as sodium benzylsulfide, phenylthiol, 2,4- dinitrophenylthiol, tritylthiol, tert-butylthiol, compounds of formula R-C(=0)-NH-CH3-SH, wherein R is methyl, tert-butyl, allyl, phenyl or benzyl, 2-trimethylsilanyl-ethanethiol, 2- (2,4-dinitrophenyl)-ethanethiol, 2-phenylsulfonyl-ethanethiol, acylated thiols, such as methylcarbonylthiol or phenylcarbonylthiol, and thiocarbamates R-NH-C(=0)-SH, wherein R is e.g. methyl or ethyl.

The benzyl and alkyl thiols are generally used in the presence of a base, such as sodium hydroxide, potassium hydroxide, sodium phosphate, potassium phosphate, sodium hydrogenphosphate, potassium hydrogenphosphate, sodium carbonate, potassium carbonate, caesium carbonate, sodium hydride, potassium hydride, lithium diisopropyl amide (LDA), sodium methanolate, sodium ethanolate, potassium tert-butoxide, aqueous sodium tetraborate, n-butyllithium, tert-butylithium, tetrabutylammoniumfluoride (TBAF), NaHMDS and the like, or in the presence of a Lewis or Bronsted acid, such as FeCIs, Zn(CI0 ₄ ) ₂ , Cu(BF ₄ ) ₂ , HBF ₄ or HCI0 ₄ .

The reaction is preferably carried out in a solvent, suitable solvents being for example chlorinated alkanes, such as methylene chloride or chloroform, and ethers, such as diethylether, dipropylether, methyl tert-butylether, methyl isobutylether, ethylenegylcol dimethylether, tetrahydrofuran (THF) or dioxane and the like.

The reaction temperature can vary over a wide range, such as from -25°C to the boiling point of the reaction mixture.

The acylated thiols can be reacted neat or in a solvent, suitable solvents being for ex- ample chlorinated alkanes, such as methylene chloride or chloroform, and ethers, such as diethylether, dipropylether, methyl tert-butylether, methyl isobutylether, ethylenegylcol dimethylether, tetrahydrofuran (THF) or dioxane and the like. They can be used with or without a base. The S-protected compound IV can then be deprotected to the free thiol IV under conditions generally known for the respective protective group, such as described, for example, in Peter G. M. Wuts, Theodora Greene, Protective Groups in Organic Synthesis, 4 ^th edition, John Wiley & Sons, Inc., 2007, Chapter 6. Among the above sulfur sources, preference is given to H2S, especially used in the presence of a base, such as Na2C03, K2CO3, CS2CO3, sodium acetate, potassium acetate, cesium acetate, amines, such as diethylamine, dipropylamine, triethylamine, diisopropylethylamine and the like, or basic nitrogen-containing heterocycles, such as pyrrolidine, piperidine, piperazine, pyridine, lutidine and the like, and preferably in the presence of an amine, such as triethylamine.

In a preferred embodiment of the method of the invention, the reaction of compound IV to compound Γ via compounds III and II is carried out as a one-pot reaction.

In an alternatively preferred embodiment of the method of the invention, the reaction of compound V to compound Γ via compounds IV, III and II is carried out as a one-pot reaction.

Compound V can be prepared in analogy to the method described in EP-A-2172462.

Compounds II (in which R ^3b is not necessarily hydrogen) can be prepared alternatively by reacting a compound of formula VII

with an amination agent to give a compound of formula VI

which reacts spontaneously to the compound II;

wherein B ¹ , B ² , B ³ , G ¹ , G ² , G ³ , G ⁴ , R ¹ , R ^3a and R ^3b are as defined above and A' is A or a precursor of A.

The reaction can be carried out in analogy to that of compounds IV and III The compound of formula VII is preferably obtained by reacting a compound of formula VIII with a compound of formula IX

The reaction is preferably carried out as a Mukaiyama aldol reaction. To this purpose, the trialklysilyl-enolate derivative of IX is reacted with VIII in the presence of a Lewis acid, such as TiCU or BF3[0(C2H ₅ )2]. Alternatively, the reaction can be carried out in the presence of a strong base, such as lithium diisopropylamide (LDA), sodium bistrime- thylsilylamide (sodium hexamethyldisilazide; NaHMDS) and amines, such as triethyla- mine, tripropylamine or diisopropylethylamine.

The reaction is generally carried out in a solvent.

If a lithium or sodium base is used, the solvent is suitably an ether, such as diethylether, dipropylether, methyl tert-butylether, methyl isobutylether, ethylenegylcol di- methylether, tetrahydrofuran (THF) or dioxane and the like. Suitable reaction temperatures range from -78 to 25°C.

If an amine base is used, the solvent is suitably an ether, such as diethylether, dipropylether, methyl tert-butylether, methyl isobutylether, ethylenegylcol dimethylether, tetrahydrofuran (THF) or dioxane, or an alkane, such as pentane, hexane or heptane. Suitable reaction temperatures range from 25 to 100°C.

The compound of formula VIII can be obtained by reacting a compound of formula X with a sulfuration agent, such as Lawesson's reagent or P2S5

The reaction is generally carried out in a solvent, suitable solvents being for example aromatic solvents, such as benzene, toluene, the xylenes, chlorobenzene or dichloro- benzene, ethers, such as diethylether, dipropylether, methyl tert-butylether, methyl iso- butylether, ethylenegylcol dimethylether, tetrahydrofuran (THF) or dioxane, and hexa- methyl phosphoric acid triamide (HMPA).

The reaction is generally carried out at a temperature of from 25°C to the boiling point of the reaction mixture.

The invention further relates to a method for preparing compounds of formula I as defined above, wherein R ¹ is CF3, which method comprises reacting a compound of for- mula XI

wherein B ¹ , B ² , B ³ , G ¹ , G ² , G ³ , G ⁴ , R ^3a and R ^3b are as defined above and A' is A or a precursor of A;

with a fluorinating agent

to give a compound I"

and, if necessary (i.e. if A is a precursor of A), converting the group A into a group A.

Suitable fluorinating agents are, for example, SF ₄ , preferably in combination with HF or BF3[0(C2H ₅ )2], phenylsulfur trifluoride (Ph-SFs), preferably in combination with HF and pyridine, 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride ("Fluoled"), and bis(2- methoxyethyl)aminosulfur trifluoride [(CHsOChbCI-b^NSFs]. Among these, preference is given to SF ₄ in combination with HF.

If SF ₄ in combination with HF is used, the reaction is carried out neat, i.e. without any further solvent. The reaction is generally carried out under elevated pressure stemming from the reactants, e.g. at a pressure of from 2 to 10 bar, preferably from 5 to 8 bar. The reaction temperature can vary over wide ranges, such as from 25 to 120°C, preferably from 60 to 100°C. Alternatively, fluorination can be carried out by a two step method, in which the carbox- yl group on the isothiazoline ring is first converted into a CC group, and this is subsequently fluorinated to the CF3 group.

The conversion of the COOH group to the CCI3 group is preferably carried out by reacting the compound VI with PCI5 and phenyl-phosphoroxy dichloride (Ph-P(=0)Cl2).

The reaction can be carried out neat, i.e. without any further solvent. Suitably, the reac- tion is carried out at elevated temperatures, for example at from 50° to reflux and preferably at reflux.

Fluorination agents for converting the CCI3 group into a CF3 group are those mentioned above, and further HF and HF in combination with SbCIs and HF in combination with Cl ₂ and SbF ₃ .

The reaction can be carried out neat, i.e. without any further solvent. The reaction temperature can vary over wide ranges, for examples from 25 to 300°C, preferably from 50 to 200°C and in particular from 80 to 120°C. If the fluorination agent is HF or HF in combination with a further agent, the reaction generally takes place at the pressure stemming from HF and ranging generally from 2 to 10 bar, preferably from 5 to 8 bar.

The compound of formula XI is preferably obtained by hydrolyzing a compound of formula XII

wherein B ¹ , B ² , B ³ , G ¹ , G ² , G ³ , G ⁴ , R ^3a and R ^3b are as defined above, A is A or a precursor of A and R is Ci-C4-alkyl.

Hydrolysis can be carried out by any suitable means known for hydrolyzing ester groups, such as acidic conditions, e.g. using hydrochloric acid, hydrobromic acid, sulfuric acid, trifluoroacetic acid, etc., or by basic conditions, e.g. using an alkali metal hydroxide, such as LiOH, NaOH or KOH, or an alkali metal carbonate, such as sodium or potassium carbonate. The compound of formula XII is in turn preferably obtained by reacting a compound XIII with a compoun

wherein B ¹ , B ² , B ³ , G ¹ , G ² , G ³ , G ⁴ , R ¹ , R ^3a and R ^3b are as defined above, A' is A or a precursor of A and R is Ci-C4-alkyl.

The reaction is carried out at elevated temperature, e.g. at from 90 to 200°C, preferably from 100 to 180°C and in particular from 120 to 160°C, e.g. at about 140°C. The compound of formula XIII can in turn be obtained by reacting a compound XVI with a compound XVII

(XVI) (XVII) The reaction is generally carried out in a solvent, suitable solvents being for example aromatic solvents, such as benzene, toluene, the xylenes, chlorobenzene and dichlo- robenzene. The reaction temoerature is preferably from 80 to 140°C, more preferably from 100 to 120°C. The invention further relates to a method for preparing compounds of formula I as defined above, wherein however R ¹ is CF3, which method comprises reacting a compound of formula XIII as define mula XV

wherein B ¹ , B ² , B ³ , R ^3a and R ^3b are as defined above,

to give a compound I"

and, if necessary, converting the group A' into a group A.

The reaction is carried out at elevated temperature, e.g. at from 90 to 200°C, preferably from 100 to 180°C and in particular from 120 to 160°C, e.g. at about 140°C.

Compounds Γ or I", in which A is a precursor of A can be converted as shown below into the different groups A ¹ to A ⁴ . Compounds Γ or I", in which A is CI, Br, I or -OS02-R ^z1 , where R ^z1 is as defined above, can be converted to compounds I wherein A is a group A ¹ , wherein A ¹ is an imino group -C(=NR ⁶ )R ⁸ , by reaction with carbon monoxide and a hydride source, such as triethylsilane, in the presence of a transition metal complex catalyst, preferably a palladium catalyst, to a carbonyl compound XVIII. This reaction converts the starting group A into a carbonyl grou

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

For obtaining compounds in which R ⁸ in the imino group is H, such carbonyl compounds XVIII are then reacted with an amine (derivative) NH2R ⁶ . Alternatively, the compound Γ or I", in which A is CI, Br, I or -OS02-R ^z1 , where R ^z1 is as defined above, can be reacted in a one pot reaction with carbon monoxide and hydrogen in the presence of a transition metal complex catalyst and the amine NH2R ⁶ . For obtaining compounds in which R ⁸ in the imino group is not H, the carbonyl compounds are reacted with a Grignard reagent R ⁸ -MgHal, where Hal is CI, Br or I, or an organolithium compound R ⁸ -Li to obtain an alcohol of formula XIX

which is then oxidized to a carbonyl compound of the formula XX

This is then reacted with an amine NH2R ⁶ to the respective imine compound.

These reactions can be carried out in analogy to the methods described in PCT/EP 201 1/060388 or in WO 2010/072781 and the references cited therein, especially WO 2006135763, Fattorusso et al, J. Med. Chem. 2008, 51 , 1333-1343 and WO

2008/122375.

Compounds I wherein A is a group A ¹ , wherein A ¹ is -S(0) _n R ⁹ or -N(R ⁵ )R ⁶ , can for ex- ample be prepared by reacting a compound Γ or I" wherein A' is CI, Br or I in a

Ullmann-type reaction with an amine NHR ⁵ R ⁶ or a thiol SHR ⁹ in the presence of a Cu(l) catalyst. To obtain a compound wherein A ¹ is -S(0) _n R ⁹ wherein n is not 0 the thiol can then be oxidized, e.g. with hydrogen peroxide. Amine and thiol groups can further be introduced in a Buchwald-Hartwig reaction by reacting a compound Γ or I" wherein A' is CI, Br or I with an amine NHR ⁵ R ⁶ or a thiol HSR ⁹ in the presence of a palladium catalyst, such as PdC (dppf) in the presence of a base, such as cesium carbonate or N,N- diisopropylethyl amine, and optionally in the presence of a phosphine ligand, such as Xantphos ("4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene").

Thioethers (A ¹ = -SR ⁹ ) can further be introduced by reacting a compound Γ or I" wherein A' is F in an SNAr reaction (nucleophilic aromatic substitution reaction) with a thiol HSR ⁹ in the presence of a base, such as potassium carbonate (K2CO3), or with a thio- late (e.g. NaSR ⁹ ).

Compounds I wherein A is a group A ² , wherein W is O and Y is OR ⁹ can be prepared by reacting a compound Γ or I" wherein A' is CI, Br, I or Otriflate with carbon monoxide in the presence of a palladium catalyst and an alcohol R ⁹ OH. Compounds I wherein A is a group A ² , wherein W is O and Y is NR ⁵ R ⁶ can be prepared by reacting a compound Γ or I" wherein A' is CI, Br, I or Otriflate with carbon monoxide in the presence of a palladium catalyst and an alcohol ROH, wherein R is Ci-C4-alkyl, to a compound of formu- la XXI. Suitable palladium catalysts are for example those described in PCT/EP 201 1/060388.

This ester is then hydrolyzed to the respective carboxylic acid, which is the reacted under standard amidation conditions with an amine NHR ⁵ R ⁶ . Hydrolyzation can be car- ried out under standard conditions, e.g. under acidic conditions using for example hydrochloric acid, sulfuric acid or trifluoroacetic acid, or under basic conditions using for example an alkali metal hydroxide, such as LiOH, NaOH or KOH. Amidation is preferably carried out by activation of the carboxylic acids with oxalylchloride [(COCI)2] or thio- nylchloride (SOC ) to the respective acid chlorides, followed by reaction with an amine NHR ⁵ R ⁶ . Alternatively, amidation is carried out in in the presence of a coupling reagent. Suitable coupling reagent (activators) are well known and are for instance selected from carbodiimides, such as DCC (dicyclohexylcarbodiimide) and DCI (diisopropylcar- bodiimide), benzotriazol derivatives, such as HATU (0-(7-azabenzotriazol-1 -yl)- Ν,Ν,Ν',Ν'-tetramethyluronium hexafluorophosphate), HBTU ((O-benzotriazol-1 -yl)- Ν,Ν,Ν',Ν'-tetramethyluronium hexafluorophosphate) and HCTU (1 H-benzotriazolium-1 - [bis(dimethylamino)methylene]-5-chloro tetrafluoroborate) and phosphonium-derived activators, such as BOP ((benzotriazol-1 -yloxy)-tris(dimethylamino)phosphonium hexafluorophosphate), Py-BOP ((benzotriazol-l -yloxy)-tripyrrolidinphosphonium hexafluorophosphate) and Py-BrOP (bromotripyrrolidinphosphonium hexafluorophosphate). Generally, the activator is used in excess. The benzotriazol and phosphonium coupling reagents are generally used in a basic medium. Compounds I wherein A is a group A ² , wherein W is S and Y is NR ⁵ R ⁶ or OR ⁹ , can be prepared by reacting the corresponding oxo-compound (W is O) with Lawesson's reagent (CAS 19172-47-5), see for example Jesberger et al., Synthesis, 2003, 1929-1958 and references therein. For compounds wherein Y is NR ⁵ R ⁶ , solvents such as HMPA or THF at an elevated temperature such as 60°C to 100°C can be used. Preferred reaction conditions are THF at 65°C. For compounds wherein Y is OR ⁹ , solvent free conditions or solvents such as toluene at temperatures such as 100°C to 200°C, preferably 140°C, are suitable reaction conditions. Compounds I wherein A is a group A ³ , wherein R ^7a and R ^7b are hydrogen, can be prepared by reducing a compound XXI or XVIII for example with LAH (lithium aluminium hydride) or DIBAL-H (diisobutyl aluminium hydride) to a compound XXII.

This is then reacted in an SN reaction with an amine NHR ⁵ R ⁶ . For this purpose, the OH group can first be converted into a better leaving group, e.g. into a sulfonate (for example mesylate, tosylate or a triflate group). If R ⁶ is a group -C(0)R ⁸ , it is alternatively possible to react compound XXII with an amine N H2R ⁵ and react then the resulting benzylic amine with an acid R ⁸ -COOH or a derivative thereof, such as its acid chloride R ⁸ -COCI, in an amidation reaction.

Compounds I wherein A is a group A ³ , wherein R ^7a is optionally substituted alkyl or optionally substituted cycloalkyl and R ^7b is hydrogen, can be prepared by subjecting a ketone XX, in which R ⁸ corresponds to R ^7a which is optionally substituted Ci-C6-alkyl c optionally substituted Cs-Cs-cycloalkyl, to a reductive amination to furnish compounds XXIII. Typical conditions for the reductive amination are: Reacting ketone XX with an amine H2N R ⁵ to yield the corresponding imine which is reduced to amine XIII with a reducing agent reagent such as Na(CN)BH3. The reaction from ketone XX to amine XXIII may also be carried out as a one pot procedure. (XXIII)

For obtaining compounds in which R ^7a and R ^7b are optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl or optionally substituted alkynyl, carbonyl compounds such as XX, in which R ⁸ corresponds to R ^7a which is optionally substituted Ci-C6-alkyl, optionally substituted Cs-Cs-cycloalkyl, optionally substituted C2-C6-alkenyl or optionally substituted C2-C6-alkynyl, is reacted with a Grignard reagent R ^7b -MgHal, where Hal is CI, Br or I, or an organolithium compound R ^7b -Li, where R ^7b is optionally substituted Ci-C6-alkyl, optionally substituted Cs-Cs-cycloalkyl, optionally substituted C2-C6-alkenyl or optionally substituted C2-C6-alkynyl, to obtain an alcohol of formula XXIV.

Alcohol XXIV can then be converted into amine XXV via the corresponding azide, as described, for example 48.

If desired, this can be converted into compounds I wherein R ⁵ and R ⁶ are different from hydrogen, for example by standard alkylation reactions.

Compounds I wherein A is a group A ³ , wherein R ^7a is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or CN and R ^7b is hydrogen, can be prepared by converting an aldehyde XVIII into an imine XXVI by reaction with an amine derivative NH2R ⁶ , wherein R ⁶ is tert-butyl sulfinyl, or, for preparing a compound with R ^7a = CN, tosylate.

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

Compounds I wherein A is a group A ³ , wherein both R ^7a and R ^7b are optionally substi- tuted alkyl, alkenyl, alkynyl, cycloalkyl or CN, can be prepared analogously by converting a ketone XX, wherein R ⁸ is has the meaning desired for R ^7b and is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or CN, into an imine by reaction with an amine derivative NH2R ⁶ , wherein R ⁶ is tert-butyl sulfinyl, or, for preparing a compound with R ^7a = CN, tosylate.

This imine is then reacted with a compound H-R ^7a in an addition reaction under condi- tions as described for example in J. Org. Chem 2002, 67, 7819-7832 and the references cited therein, or, for introducing CN as a group R ^7a , Chemistry - A European Journal 2009, 15, 1 1642-1 1659.

If desired, R ⁶ can then be removed to yield an amino group NH2.

Compounds I wherein A is A ⁴ can be prepared by standard ring coupling reactions. For example, compounds, wherein A ⁴ is an N-bound heterocyclic ring can be prepared by reacting a compound Γ or I" wherein A' is CI, Br or I with the respective ring A ⁴ -H (H being on the nitrogen ring atom to be coupled) under Ullmann coupling conditions, such as described, for example, in WO 2007/075459. Typically, copper(l) iodide or copper(l) oxide and a ligand such as 1 ,2-cyclohexyldiamine is used, see for example Kanemasa et al., European Journal of Organic Chemistry, 2004, 695-709. If A' is F, the reaction is typically run in a polar aprotic solvent such as Ν,Ν-dimethylformamide, N,N- dimethylacetamide or N-methylpyrrolidone, and in the presence of an inorganic base such as sodium, potassium or cesium carbonate.

Compounds, wherein A ⁴ is a C-bound heterocyclic ring can be prepared by reacting a compound Γ or I" wherein A is Br or I with the boronic acid of the respective ring A ⁴ - B(OH)2 or the boronate ester of the respective ring A ⁴ -B(OR2) under Suzuki reaction conditions via Pd-catalyzed cross coupling, such as described, for example, in WO 2007/075459. A typical catalyst is tetrakis(triphenylphosphine)palladium(0). Solvents such as tetrahydrofuran, acetonitrile, diethyl ether and dioxane are suitable. The boronic acids A ⁴ -B(OH)2 are either commercially available or can be prepared by known methods. Other methods for introduction of the heterocyclic groups A ⁴ are the Heck, Stille, Kumada and Buchwald-Hartwig coupling procedures; see for example Tetrahedron, 2004, 60, 8991 -9016.

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

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

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

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

Such a composition may comprise a single active compound of the present invention or a mixture of several active compounds of the present invention. The composition according to the present invention may comprise an individual isomer or mixtures of isomers or a salt as well as individual tautomers or mixtures of tautomers.

The compounds of the present invention, including their salts, stereoisomers and tau- tomers, are in particular suitable for efficiently controlling arthropodal pests such as arachnids, myriapedes and insects as well as nematodes. They are especially suitable for efficiently combating or controlling the following pests: Insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Chei- matobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosel- la, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliar- ia, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fis- cellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blan- cardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Pieris rapae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacio- nia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis; beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscur- us, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus po- morum, Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Blastopha- gus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus len- tis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthor- rhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vesperti- nus, Crioceris asparagi, Ctenicera ssp., Diabrotica longicornis, Diabrotica semipunc- tata, Diabrotica 12-punctata Diabrotica speciosa, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brun- neipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptino- tarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobi- us pyri, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus grana- ria; flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anas- trepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles mini- mus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrys- ops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus cucurbi- tae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gaster- ophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phor- bia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga spp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Taba- nus similis, Tipula oleracea, and Tipula paludosa; thrips (Thysanoptera), e.g. Dichromothrips corbetti, Dichromothrips ssp., Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci, termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Re- ticulitermes santonensis, Reticulitermes grassei, Termes natalensis, and Coptotermes formosanus; cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Peri- planeta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis; bugs, aphids, leafhoppers, whiteflies, scale insects, cicadas (Hemiptera), e.g.

Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solu- bea insularis, Thyanta perditor, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisia argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, Brachycau- dus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmanni- anae, 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, Myzus persicae, Myzus ascalo- nicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi,

Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera au- rantiiand, Viteus vitifolii, Cimex lectularius, Cimex hemipterus, Reduvius senilis, Tria- toma spp., and Arilus critatus; ants, bees, wasps, sawflies (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Lasius niger, Mon- omorium pharaonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, So- lenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex californicus, Pheidole meg- acephala, Dasymutilla occidentalis, Bombus spp., Vespula squamosa, Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolichovespula macula- ta, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile; crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica, Gryllotalpa gryllo- talpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus italicus, Chortoicetes terminifera, and Locustana pardalina; arachnoidea, such as arachnids (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Ambryomma maculatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Dermacentor andersoni, Dermacentor variabilis, Hy- alomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ixodes scapularis, Ixodes holo- cyclus, Ixodes pacificus, Ornithodorus moubata, Ornithodorus hermsi, Ornithodorus turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis;

Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai,

Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ul- mi, Panonychus citri, and Oligonychus pratensis; Araneida, e.g. Latrodectus mactans, and Loxosceles reclusa; fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus, silverfish, firebrat (Thysanura), e.g. Lepisma saccharina and Thermobia domestica, centipedes (Chilopoda), e.g. Scutigera coleoptrata, millipedes (Diplopoda), e.g. Narceus spp.,

Earwigs (Dermaptera), e.g. forficula auricularia, lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bo- vicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus. Collembola (springtails), e.g. Onychiurus ssp..

The compounds of the present invention, including their salts, stereoisomers and tau- tomers, are also suitable for controlling nematodes : plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javani- ca, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, An- guina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bur- saphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Crico- nema species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Helio- cotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Ro- tylenchus robustus and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species.

The compounds of the present invention, including their salts, stereoisomers and tau- tomers, are particularly useful for controlling insects, preferably sucking or piercing and chewing and biting insects such as insects from the genera Lepidoptera, Coleoptera and Hemiptera, in particular Lepidoptera, Coleoptera and true bugs.

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

The compounds of the present invention, including their salts, stereoisomers and tau- tomers, are particularly useful for controlling insects of the orders Lepidoptera and Coleoptera.

The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.

An agrochemical composition comprises a pesticidally effective amount of a compound I. The term "effective amount" denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the species to be controlled, the treated cultivated plant or material, the climat- ic conditions and the specific compound I used.

The compounds I, their N-oxides and salts can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emul- sions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6 ^th Ed. May 2008, CropLife International.

The compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F In- forma, London, 2005.

Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dis- persants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders. Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetra- hydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phospho- nates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kao- lins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in

McCutcheon' s, Vol.1 : Emulsifiers & Detergents, McCutcheon' s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.). Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sul- fonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccin- ates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinyl- alcohols, or vinylacetate. Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, poly- ethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or pol- ybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5. Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothia- zolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids. Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants). Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

Examples for composition types and their preparation are:

i) Water-soluble concentrates (SL, LS)

10-60 wt% of a compound I according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) ad 100 wt%. The active substance dissolves upon dilution with water.

ii) Dispersible concentrates (DC)

5-25 wt% of a compound I according to the invention and 1 -10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclohexanone) ad

100 wt%. Dilution with water gives a dispersion.

iii) Emulsifiable concentrates (EC)

15-70 wt% of a compound I according to the invention and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water- insoluble organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion.

iv) Emulsions (EW, EO, ES)

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

v) Suspensions (SC, OD, FS)

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

vi) Water-dispersible granules and water-soluble granules (WG, SG)

50-80 wt% of a compound I according to the invention are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt%and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

50-80 wt% of a compound I according to the invention are ground in a rotor-stator mill with addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.

viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt% of a compound I according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

iv) Microemulsion (ME)

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

iv) Microcapsules (CS)

An oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dis- persed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of

poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethene-4,4' - diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of a polyurea microcapsules. The monomers amount to 1 -10 wt%. The wt% relate to the total CS composition.

ix) Dustable powders (DP, DS)

1 -10 wt% of a compound I according to the invention are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt%. x) Granules (GR, FG)

0.5-30 wt% of a compound I according to the invention is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%. Granulation is achieved by extrusion, spray-drying or the fluidized bed.

xi) Ultra-low volume liquids (UL)

1 -50 wt% of a compound I according to the invention are dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%.

The compositions types i) to xi) may optionally comprise further auxiliaries, such as 0,1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1 -1 wt% anti-foaming agents, and 0,1 -1 wt% colorants.

The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active sub- stance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

Solutions for seed treamtent (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying compound I and compositions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, compound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.

When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.

In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required. When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect.

Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, prefera- bly 0.005 g to 1 kg, of active substance per cubic meter of treated material.

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

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

According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate. In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e. g. components comprising compounds I and/or active substances from the groups M) or F) (see below), may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.

In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e. g. components comprising compounds I and/or active substances from the groups M) or F) (see below), can be applied jointly (e.g. after tank mix) or consecutively. The following categorized list M of pesticides represents insecticidal mixture partners, which are, whenever possible, classified according to the Insecticide Resistance Action Committee (IRAC), and together with which the compounds according to the present invention may be used. The combined use of the compounds of the present invention with the following pesticides may result in potential synergistic effects. The following examples of insecticidal mixing partners are provided with the intention to illustrate the possible combinations, but not to impose any limitation to the obtainable mixtures:

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

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

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

M.2. GABA-gated chloride channel antagonists such as:

M.2A cyclodiene organochlorine compounds, as for example endosulfan or chlordane; or

M.2B fiproles (phenylpyrazoles), as for example ethiprole, fipronil, flufiprole, pyra- fluprole and pyriprole;

M.3 Sodium channel modulators from the class of

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

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

M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class of

M.4A neonicotinoids, for example acteamiprid, chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or

M.4B nicotine.

M.5 Nicotinic acetylcholine receptor allosteric activators from the class of spinosyns, for example spinosad or spinetoram; M.6 Chloride channel activators from the class of avermectins and milbemycins, for example abamectin, emamectin benzoate, ivermectin, lepimectin or milbemectin;

M.7 Juvenile hormone mimics, such as

M.7A juvenile hormone analogues as hydroprene, kinoprene and methoprene; or others as

M.7B fenoxycarb, or

M.7C pyriproxyfen; M.8 miscellaneous non-specific (multi-site) inhibitors, for example

M.8A alkyl halides as methyl bromide and other alkyl halides, or

M.8B chloropicrin, or

M.8C sulfuryl fluoride, or

M.8D borax, or

M.8E tartar emetic;

M.9 Selective homopteran feeding blockers, for example

M.9B pymetrozine, or

M.9C flonicamid;

M.10 Mite growth inhibitors, for example

M.10A clofentezine, hexythiazox and diflovidazin, or

M.10B etoxazole; M.1 1 Microbial disruptors of insect midgut membranes, for example bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. israelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebri- onis, or the Bt crop proteins: CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1 ;

M.12 Inhibitors of mitochondrial ATP synthase, for example

M.12A diafenthiuron, or

M.12B organotin miticides such as azocydotin, cyhexatin or fenbutatin oxide, or M.12C propargite, or

M.12D tetradifon;

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

M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, for example nereis- toxin analogues as bensultap, cartap hydrochloride, thiocyclam or thiosultap sodium; M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas as for example bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron or triflumuron;

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

M.17 Moulting disruptors, Dipteran, as for example cyromazine; M.18 Ecdyson receptor agonists such as diacylhydrazines, for example methoxyfeno- zide, tebufenozide, halofenozide, fufenozide or chromafenozide;

M.19 Octopamin receptor agonists, as for example amitraz; M.20 Mitochondrial complex III electron transport inhibitors, for example

M.20A hydramethylnon, or

M.20B acequinocyl, or

M.20C fluacrypyrim; M.21 Mitochondrial complex I electron transport inhibitors, for example

M.21A METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidif- en, pyridaben, tebufenpyrad or tolfenpyrad, or

M.21 B rotenone; M.22 Voltage-dependent sodium channel blockers, for example

M.22A indoxacarb, or

M.22B metaflumizone;

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

M.24 Mitochondrial complex IV electron transport inhibitors, for example

M.24A phosphine such as aluminium phosphide, calcium phosphide, phosphine or zinc phosphide, or

M.24B cyanide.

M.25 Mitochondrial complex II electron transport inhibitors, such as beta-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen; M.28 Ryanodine receptor-modulators from the class of diamides, as

for example flubendiamide, chloranthraniliprole (rynaxypyr®), cyanthraniliprole (cyazypyr®), or the phthalamide compounds

M.28.1 : (R)-3-Chlor-N1 -{2-methyl-4-[1 ,2,2,2-tetrafluor-1 -(trifluormethyl)ethyl]phenyl}- N2-(1 -methyl-2-methylsulfonylethyl)phthalamid and

M.28.2: (S)-3-Chlor-N1 -{2-methyl-4-[1 ,2,2,2-tetrafluor-1 -(trifluormethyl)ethyl]phenyl}- N2-(1 -methyl-2-methylsulfonylethyl)phthalamid, or the compound

M.28.3: 3-bromo-N-{2-bromo-4-chloro-6-[(1 -cyclopropylethyl)carbamoyl]phenyl}-1 -(3- chlorpyridin-2-yl)-1 H-pyrazole-5-carboxamide, or the compound

M.28.4: methyl-2-[3,5-dibromo-2-({[3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-5- yl]carbonyl}amino)benzoyl]-1 ,2-dimethylhydrazinecarboxylate;

M.X insecticidal active compounds of unknown or uncertain mode of action, as for example azadirachtin, amidoflumet, benzoximate, bifenazate, bromopropylate, chinome- thionat, cryolite, dicofol, flufenerim, flometoquin, fluensulfone, flupyradifurone, piperonyl butoxide, pyridalyl, pyrifluquinazon, sulfoxaflor, or the compound

M.X.1 : 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-iso xazol-3-yl]-2-methyl- N-[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzamide, or the compound

M.X.2: cyclopropaneacetic acid, l .l'- S^R^aR.eS.eaS.^R.^aS.^bSH-I^- cyclopropylacetyl)oxy]methyl]-1 ,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy- 4,6a, 12b-trimethyl-1 1 -oxo-9-(3-pyridinyl)-2H , 1 1 H-naphtho[2, 1 -b]pyrano[3,4-e]pyran- 3,6-diyl] ester, or the compound

M.X.3: 1 1 -(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]- tetradec-1 1 -en-10-one, or the compound

M.X.4: 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1 -azaspiro[4.5]dec-3-en- 2-one, or the compound

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

The commercially available compounds of the group M listed above may be found in The Pesticide Manual, 15th Edition, C. D. S. Tomlin, British Crop Protection Council (201 1 ) among other publications.

The phthalamides M.28.1 and M.28.2 are both known from WO 2007/101540. The an- thranilamide M.28.3 has been described in WO2005/077943. The hydrazide compound M.28.4 has been described in WO 2007/043677.-The quinoline derivative flometoquin is shown in WO2006/013896. The aminofuranone compounds flupyradifurone is known from WO 2007/1 15644. The sulfoximine compound sulfoxaflor is known from

WO2007/149134. The isoxazoline compound M.X.1 has been described in

WO2005/085216. The pyripyropene derivative M.X.2 has been described in WO 2006/129714. The spiroketal-substituted cyclic ketoenol derivative M.X.3 is known from WO2006/089633 and the biphenyl-substituted spirocyclic ketoenol derivative M.X.4 from WO2008/06791 1. Finally triazoylphenylsulfide like M.X.5 have been described in WO2006/043635 and biological control agents on basis of bacillus firmus in

WO2009/124707. The following list F of active substances, in conjunction with which the compounds according to the invention can be used, is intended to illustrate the possible combinations but does not limit them:

F.I) Respiration Inhibitors

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

strobilurins: azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, ene- stroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, triclopyricarb/chlorodin- carb, trifloxystrobin, 2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methyl ester and 2 (2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)- phenyl)-2-methoxyimino-N methyl-acetamide;

oxazolidinediones and imidazolinones: famoxadone, fenamidone;

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

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

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

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

diflumetorim; tecnazen; ferimzone; ametoctradin; silthiofam;

nitrophenyl derivates: binapacryl, dinobuton, dinocap, fluazinam, nitrthal-isopropyl, organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide;

F.ll) Sterol biosynthesis inhibitors (SBI fungicides)

F.II-1 ) C14 demethylase inhibitors (DMI fungicides, e.g. triazoles, imidazoles) triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusi- lazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobu- tanil, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole;

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

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

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

morpholines: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph; piperidines: fenpropidin, piperalin; spiroketalamines: spiroxamine;

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

F.lll) Nucleic acid synthesis inhibitors

F.III-1 ) RNA, DNA synthesis

phenylamides or acyl amino acid fungicides: benalaxyl, benalaxyl-M, kiralaxyl, met- alaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl;

isoxazoles and iosothiazolones: hymexazole, octhilinone;

F.III-2) DNA topisomerase inhibitors: oxolinic acid;

F.III-3) Nucleotide metabolism (e.g. adenosin-deaminase)

hydroxy (2-amino)-pyrimidines: bupirimate;

F.IV) Inhibitors of cell division and or cytoskeleton

F.IV-1 ) Tubulin inhibitors: benzimidazoles and thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl;

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

F.IV-2) Other cell division inhibitors

benzamides and phenyl acetamides: diethofencarb, ethaboxam, pencycuron, fluopico- lide, zoxamide;

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

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, mildiomy- cin, streptomycin, oxytetracyclin, polyoxine, validamycin A;

F.VI) Signal transduction inhibitors

F.VI-1 ) MAP / Histidine kinase inhibitors (e.g. anilino-pyrimidines)

dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin;

phenylpyrroles: fenpiclonil, fludioxonil;

F.VI-2) G protein inhibitors: quinolines: quinoxyfen;

F.VI I) Lipid and membrane synthesis inhibitors

F.VI 1-1 ) Phospholipid biosynthesis inhibitors

organophosphorus compounds: edifenphos, iprobenfos, pyrazophos;

dithiolanes: isoprothiolane;

F.VII-2) Lipid peroxidation

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

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

cinnamic or mandelic acid amides: dimethomorph, flumorph, mandiproamid, pyrimorph; valinamide carbamates: benthiavalicarb, iprovalicarb, pyribencarb, valifenalate and N- (1 -(1 -(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester; F.VII-4) Compounds affecting cell membrane permeability and fatty 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, hexachlorobenzene, pentachlorphenole and its salts, phthalide, tolylfluanid, N- (4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamid e;

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

F.VIII-5) Ahtraquinones: dithianon;

F.IX) Cell wall synthesis inhibitors

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

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

F.X) Plant defence inducers

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

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

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

F.XI) Unknown mode of action:

bronopol, chinomethionat, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat-methylsulfate, diphenylamin, flumetover, flusulfamide, flutianil, methasulfocarb, oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide, 2-but- oxy-6-iodo-3-propylchromen-4-one, N-(cyclopropylmethoxyimino-(6-difluoro-methoxy- 2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide, N'-(4-(4-chloro-3-trifluoromethyl- phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N methyl formamidine, N' (4-(4-fluoro-3-trifluoro- methyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N'-(2-methyl-5- trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-eth yl-N-methyl formamidine, N'- (5-difluoromethyl-2 methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-meth yl formamidine, 2-{1 -[2-(5-methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]-piperidin-4-yl}- thiazole-4-carboxylic acid methyl-(1 ,2,3,4-tetrahydro-naphthalen-1 -yl)-amide, 2-{1 -[2- (5-methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid methyl-(R)-1 ,2,3,4-tetrahydro-naphthalen-1 -yl-amide, methoxy-acetic acid 6-tert- butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester and N-Methyl-2-{1 -[(5-methyl-3-trifluoro- methyl-1 H-pyrazol-1 -yl)-acetyl]-piperidin-4-yl}-N-[(1 R)-1 ,2,3,4-tetrahydronaphthalen-1 - yl]-4-thiazolecarboxamide, 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyri- dine, pyrisoxazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro-pyrazole -1 car- bothioic acid S-allyl ester, N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid am- ide, 5-chloro-1 (4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole, 2-(4-chlo- ro-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, dikegu- lac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N 6 benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5 tri iodobenzoic acid, trinexapac-ethyl and uniconazole;

F.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 pumilus strain with NRRL No. B-30087 (e.g. SONATA® and BALLAD® Plus from AgraQuest, Inc., USA), Ulocladium oudemansii (e.g. the product BOTRY- ZEN from BotriZen Ltd., New Zealand), Chitosan (e.g. ARMOUR-ZEN from BotriZen Ltd., New Zealand).

The invertebrate pest (also referred to as "animal pest"), i.e. the insects, arachnids and nematodes, the plant, soil or water in which the plant is growing or may grow can be contacted with the compounds of the present invention or composition(s) comprising them by any application method known in the art. As such, "contacting" includes both direct contact (applying the compounds/compositions directly on the invertebrate pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (apply- ing the compounds/compositions to the locus of the invertebrate pest or plant).

The compounds of the present invention or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by animal pests, especially insects, acaridae or arachnids by contacting the plant/crop with a pesticidally effective amount of compounds of the present invention. The term "crop" refers both to growing and harvested crops.

The compounds of the present invention and the compositions comprising them are particularly important in the control of a multitude of insects on various cultivated plants, such as cereal, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sug- ar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.

The compounds of the present invention are employed as such or in form of compositions by treating the insects or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from insecticidal attack with an insec- ticidally effective amount of the active compounds. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the insects.

Moreover, invertebrate pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of compounds of the present invention. As such, the application may be carried out before or after the infection of the locus, growing crops, or harvested crops by the pest.

The compounds of the present invention can also be applied preventively to places at which occurrence of the pests is expected.

The compounds of the present invention may be also used to protect growing plants from attack or infestation by pests by contacting the plant with a pesticidally effective amount of compounds of the present invention. As such, "contacting" includes both direct contact (applying the compounds/compositions directly on the pest and/or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the pest and/or plant).

"Locus" means a habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest or parasite is growing or may grow.

In general, "pesticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of applica- tion, 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 m ² , preferably from 0.001 to 20 g per 100 m ² . Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compound per m ² treated material, desirably from 0.1 g to 50 g per m ² .

Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and/or insecticide.

For use in treating crop plants, the rate of application of the active ingredients of this invention may be in the range of 0.1 g to 4000 g per hectare, desirably from 5 g to 500 g per hectare, more desirably from 5 g to 200 g per hectare.

The compounds of the present invention are effective through both contact (via soil, glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait, or plant part).

The compounds of the present invention may also be applied against non-crop insect pests, such as ants, termites, wasps, flies, mosquitos, crickets, or cockroaches. For use against said non-crop pests, compounds of the present invention are preferably used in a bait composition.

The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks. Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources. Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickyness, moisture retention or aging characteristics. The bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cock- roaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.

For use in bait compositions, the typical content of active ingredient is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active ingredient.

Formulations of compounds of the present invention as aerosols (e.g in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are prefer- ably composed of the active compound, solvents such as lower alcohols (e.g. methanol, ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g. kerosenes) having boiling ranges of approximately 50 to 250 °C, dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethox- ylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzo- ate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, pro- pellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.

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

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

The compounds of the present invention and its respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.

Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of the present invention and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tset- se-fly trap or the like. Insecticidal compositions for application to fibers, fabric, knit- goods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder. Suitable repellents for example are Ν,Ν-Diethyl-meta-toluamide (DEET), N,N- diethylphenylacetamide (DEPA), 1 -(3-cyclohexan-1 -yl-carbonyl)-2-methylpiperine, (2- hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-1 ,3-hexandiol, indalone, Methyl- neodecanamide (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 ver- satate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2- ethylhexylacrylate, and methyl acrylate, mono- and di-ethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadiene.

The impregnation of curtains and bednets is done in general by dipping the textile material into emulsions or dispersions of the insecticide or spraying them onto the nets. The compounds of the present invention and their compositions can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities). The compounds of the present invention are applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, plywoods, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insulating material such as styrene foams, etc. In case of application against ants doing harm to crops or human beings, the ant controller of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like. The compounds of the present invention are also suitable for the treatment of plant propagation material, especially seeds, in order to protect them from insect pest, in particular from soil-living insect pests and the resulting plant' s roots and shoots against soil pests and foliar insects.

The compounds of the present invention are particularly useful for the protection of the seed from soil pests and the resulting plant' s roots and shoots against soil pests and foliar insects. The protection of the resulting plant' s roots and shoots is preferred. More preferred is the protection of resulting plant' s shoots from piercing and sucking insects, wherein the protection from aphids is most preferred.

The present invention therefore comprises a method for the protection of seeds from insects, in particular from soil insects and of the seedlings' roots and shoots from insects, in particular from soil and foliar insects, said method comprising contacting the seeds before sowing and/or after pregermination with a compound of the present invention, including a salt thereof. Particularly preferred is a method, wherein the plant' s roots and shoots are protected, more preferably a method, wherein the plants shoots are protected form piercing and sucking insects, most preferably a method, wherein the plants shoots are protected from aphids.

The term seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like and means in a preferred embodiment true seeds. The term seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting.

The present invention also comprises seeds coated with or containing the active com- pound.

The term "coated with and/or containing" generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.

Suitable seed is seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.

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

For example, the active compound can be employed in treatment of seeds from plants, which are resistant to herbicides from the group consisting of the sulfonylureas, imid- azolinones, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active substances (see for example, EP-A 242 236, EP-A 242 246) (WO 92/00377) (EP-A 257 993, U.S. 5,013,659) or in transgenic crop plants, for example cotton, with the capability of producing Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP-A 142 924, EP-A 193 259),

Furthermore, the active compound can be used also for the treatment of seeds from plants, which have modified characteristics in comparison with existing plants consist, which can be generated for example by traditional breeding methods and/or the generation of mutants, or by recombinant procedures). For example, a number of cases have been described of recombinant modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO 92/1 1376, WO 92/14827, WO

91/19806) or of transgenic crop plants having a modified fatty acid composition (WO 91/13972).

The seed treatment application of the active compound is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants. Compositions which are especially useful for seed treatment are e.g.:

A Soluble concentrates (SL, LS)

D Emulsions (EW, EO, ES)

E Suspensions (SC, OD, FS)

F Water-dispersible granules and water-soluble granules (WG, SG)

G Water-dispersible powders and water-soluble powders (WP, SP, WS)

H Gel-Formulations (GF)

I Dustable powders (DP, DS) Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter.

In a preferred embodiment a FS formulation is used for seed treatment. Typcially, a FS formulation may comprise 1 -800 g/l of active ingredient, 1 -200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.

Especially preferred FS formulations of compounds of the present invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient, from 0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g. 1 to 40 % by weight of a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.

Seed Treatment formulations may additionally also comprise binders and optionally colorants.

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

Examples of a gelling agent is carrageen (Satiagel ^® )

In the treatment of seed, the application rates of the compounds of the present invention are generally from 0.01 g to 10 kg per 100 kg of seed, preferably from 0.05 g to 5 kg per 100 kg of seed, more preferably from 0.1 g to 1000 g per 100 kg of seed and in particular from 0.1 g to 200 g per 100 kg of seed.

The invention therefore also relates to seed comprising a compound of the present invention, including an agriculturally useful salt of it, as defined herein. The amount of the compound of the present invention, including an agriculturally useful salt thereof will in general vary from 0.01 g to 10 kg per 100 kg of seed, preferably from 0.05 g to 5 kg per 100 kg of seed, in particular from 0.1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.

Methods which can be employed for treating the seed are, in principle, all suitable seed treatment and especially seed dressing techniques known in the art, such as seed coating (e.g. seed pelleting), seed dusting and seed imbibition (e.g. seed soaking). Here, "seed treatment" refers to all methods that bring seeds and the compounds of the present invention into contact with each other, and "seed dressing" to methods of seed treatment which provide the seeds with an amount of the compounds of the present invention, i.e. which generate a seed comprising a compound of the present invention. In principle, the treatment can be applied to the seed at any time from the harvest of the seed to the sowing of the seed. The seed can be treated immediately be- fore, or during, the planting of the seed, for example using the "planter's box" method. However, the treatment may also be carried out several weeks or months, for example up to 12 months, before planting the seed, for example in the form of a seed dressing treatment, without a substantially reduced efficacy being observed. Expediently, the treatment is applied to unsown seed. As used herein, the term "unsown seed" is meant to include seed at any period from the harvest of the seed to the sowing of the seed in the ground for the purpose of germination and growth of the plant. Specifically, a procedure is followed in the treatment in which the seed is mixed, in a suitable device, for example a mixing device for solid or solid/liquid mixing partners, with the desired amount of seed treatment formulations, either as such or after previous dilution with water, until the composition is distributed uniformly on the seed. If ap- propriate, this is followed by a drying step.

The compounds of the present invention, including their stereoisomers, veterinarily acceptable salts or N-oxides, are in particular also suitable for being used for combating parasites in and on animals.

An object of the present invention is therfore also to provide new methods to control parasites in and on animals. Another object of the invention is to provide safer pesticides for animals. Another object of the invention is further to provide pesticides for animals that may be used in lower doses than existing pesticides. And another object of the invention is to provide pesticides for animals, which provide a long residual con- trol of the parasites.

The invention also relates to compositions comprising a parasiticidally effective amount of compounds of the present invention, including their stereoisomers, veterinarily acceptable salts or N-oxides, and an acceptable carrier, for combating parasites in and on animals.

The present invention also provides a method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of the present invention, including its stereoisomers, veterinarily acceptable salts or N-oxides, or a composition comprising it.

The invention also provides a process for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises a parasiticidally effective amount of a compound of the present invention, including its stereoisomers, veterinarily acceptable salts or N-oxides, or a composition comprising it.

Activity of compounds against agricultural pests does not suggest their suitability for control of endo- and ectoparasites in and on animals which requires, for example, low, non-emetic dosages in the case of oral application, metabolic compatibility with the animal, low toxicity, and a safe handling.

Surprisingly it has now been found that compounds of formula (I) and their stereoiso- mers, veterinarily acceptable salts, tautomers and N-oxides, are suitable for combating endo- and ectoparasites in and on animals.

The compounds of the present invention, especially compounds of formula (I) and their stereoisomers, veterinarily acceptable salts, tautomers and N-oxides, and compositions comprising them are preferably used for controlling and preventing infestations of and infections in animals including warm-blooded animals (including humans) and fish. They are for example suitable for controlling and preventing infestations and infections in mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur- bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels. Compounds of the present invention, including their stereoisomers, veterinarily acceptable salts or N-oxides, and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals, such as dogs or cats.

Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chig- gers, gnats, mosquitoes and fleas.

The compounds of the present invention, including their stereoisomers, veterinarily acceptable salts or N-oxides, and compositions comprising them are suitable for systemic and/or non-systemic control of ecto- and/or endoparasites. They are active against all or some stages of development.

The compounds of the present invention are especially useful for combating parasites of the following orders and species, respectively:

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus,

cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Peri- planeta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis,

flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anas- trepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inor- nata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intes- tinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Lep- toconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus ar- gentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcoph- aga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Taba- nus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bo- vicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus. ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni,

Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodo- rus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonys- sus bacoti and Dermanyssus gallinae,

Actinedida (Prostigmata) und Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., and Laminosioptes spp, Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Arilus critatus,

Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp,

Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Tricho- dectes spp., and Felicola spp,

Roundworms Nematoda:

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

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

Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunosto- mum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oe- sophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stepha- nurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus, and Dioc- tophyma renale,

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

Camallanida, e.g. Dracunculus medinensis (guinea worm)

Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habro- nema spp., Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp.,

Macracanthorhynchus hirudinaceus and Oncicola spp,

Planarians (Plathelminthes):

Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicro- coelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilhar- zia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp,

Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp.

The present invention relates to the therapeutic and the non-therapeutic use of compounds of the present invention and compositions comprising them for controlling and/or combating parasites in and/or on animals. The compounds of the present inven- tion and compositions comprising them may be used to protect the animals from attack or infestation by parasites by contacting them with a parasiticidally effective amount of compounds of the present invention and compositions containing them.

The compounds of the present invention and compositions comprising them can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits). As such, "contacting" includes both direct contact (applying the pesticidal mixtures/compositions containing the compounds of the present invention directly on the parasite, which may include an indirect contact at its locus-P, and optionally also administrating the pesticidal mixtures/composition directly on the animal to be protected) and indirect contact (applying the compounds/compositions to the locus of the parasite). The contact of the parasite through application to its locus is an example of a non-therapeutic use of compounds of the present invention. "Locus-P" as used above means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal.

In general, "parasiticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions of the present invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing condi- tions such as desired parasiticidal effect and duration, target species, mode of application, and the like.

The compounds of the present invention can also be applied preventively to places at which occurrence of the pests or parasites are expected.

Administration can be carried out both prophylactically and therapeutically. Administration of the active compounds is carried out directly or in the form of suitable preparations, orally, topically/dermally or parenterally.

The compounds of the invention have a distinctly shorter half live in the soil and thus are significantly less persistent than isoxazoline compounds of similar structure and insecticidal activity.

Examples The present invention is now illustrated in further details by the following examples, without imposing any limitation thereto.

Preparation Examples

Compounds can be characterized e.g. by coupled High Performance Liquid Chroma- tography / mass spectrometry (HPLC/MS), by ¹ H-NMR and/or by their melting points. Analytical HPLC column:

Method A: Analytical UPLC column: RP-18 column Chromolith Speed ROD, 50 x 4.6 mm, from Merck KgaA, Germany). Elution: acetonitrile + 0.1 % trifluoroacetic acid (TFA) / water + 0.1 % trifluoroacetic acid (TFA) in a ratio of from 5:95 to 95:5 in 5 minutes at 40 °C. Flow: 1.8 mL/min. MS-method: ESI positive.

Method B: Analytical UPLC column: Phenomenex Kinetex 1 ,7 μηι XB-C18 100A; 50 x 2.1 mm from Phenomenex, Germany. Elution: acetonitrile + 0.1 % trifluoroacetic acid (TFA) / water + 0.1 % trifluoroacetic acid (TFA) in a ratio from 5:95 to 100:0 in 1 .5 min at 60 °C. Flow: 0.8 mL/min to 1 mL/min in 1.5 min. MS-method: ESI positive.

1H-NMR, respectively ¹³ C-NMR: The signals are characterized by chemical shift (ppm, δ [delta]) vs. tetramethylsilane, respectively CDC for ¹³ C-NMR, by their multiplicity and by their integral (relative number of hydrogen atoms given). The following abbreviations are used to characterize the multiplicity of the signals: m = multiplett, q = quartett, t = triplett, d = doublet and s = singulett.

Abbreviations used are: h for hour(s), min for minute(s), r.t./room temperature for 20- 25°C, THF for tetrahydrofuran, OAc for acetate.

C.1 Compound examples 1

Compound examples 1 -1 to 1 -20 correspond to compounds of formula C.1 :

wherein R ^2a , R ^2b , R ^2c , R ⁴ , and R ⁶ of each synthesized compound is defined of table C.1 below.

The compounds were synthesized in analogy to Synthesis Example S.1 .

Table d

C.2 Compound examples 2 Compound examples 2-1 to 2-233 correspond to compounds of formula C.2:

wherein R ^2a , R ^2b , R ^2c , R ⁴ , and Y of each synthesized compound is defined in one row of table C.2 below.

The compounds were synthesized in analogy to Synthesis Example S.2.

Table C.2

Ex. R2a, R2b, R2c R4 Y HPLC-MS:

Method, Rt (min) & [M+H] ⁺ or

1 H-NMR

2-1 CI, H, CI CH ₃ NHCH ₂ C(=0)-NHCH ₂ CF ₃ A 4.242 572.0

NHCH ₂ C(=0)-

2-2 CI, H, CI CH ₃ B 1.348 530.1

NHCH ₂ (cyclopropyl)

Ex. R2< R2b, R2c R4 Y HPLC-MS:

Method, Rt (min) & [M+H] ⁺

1 H-NMR

(s, 2H), 4.2 (d, 1 H), 3.9 (d, 1 H)

2-37 CI, H, CI CI NHCH ₂ -(4-pyridyl) B 1.150 544.2

2-38 CI, H, CI CI NH-CeHs B 1.508 530.9

2-39 CI, H, CI CI NHCH ₂ -(6-CI-pyrid-3-yl) B 1.447 580.0

NH-(1 , 1-dioxo-thiethan-3-

2-40 CI, H, CI CI B 1.196 557.0

yi)

2-41 CI, H, CI F NHCH ₂ -(4-thiazolyl) B 1.396 534.0

2-42 CI, H, CI CI NH-(3-pyridyl) B 1.202 531.9

NHCH ₂ -(3,3-difluoro-

2-43 CI, H, CI CH ₃ cyclobut-1-yl) B 1.466 537.3

2-44 CI, H, CI CI NH-(2-pyridyl) B 1.429 531 .8

2-45 CI, H, CI CI NH-(4-pyridyl) B 1.170 532.0

2-46 CI, H, CI CH ₃ NH-CH ₂ -(2-nitrophenyl) B 1.485 568.3

2-47 CI, H, CI CI N(CH ₃ )-CH ₂ -(2-pyridyl) B 1.314 560.0

2-48 CI, H, CI CI NHCH ₂ -(4-pyrimidyl) B 1.343 546.8

N(CH ₂ CH ₃ )-CH ₂ -(2-

2-49 CI, H, CI CI B 1.338 573.8

pyridyl)

2-50 CI, H, CI CI NHCH ₂ -(2-pyrimidyl) B 1.374 547.4

2-51 CI, H, CI CH ₃ NHCH ₂ -(cyclobutyl) B 1.51 1 501 .1

2-52 CI, H, CI CH ₃ NHCH ₂ -(cyclopentyl) B 1.546 516.8

2-53 CI, H, CI CH ₃ NHCH ₂ -(2-pyrazinyl) B 1.353 525.0

2-54 CI, H, CI CH ₃ NHCH ₂ -(3-pyridyl) B 1.128 524.3

2-55 CI, H, CI CH ₃ NHCH ₂ -(4-pyridyl) B 1.130 524.2

2-56 CI, H, CI CH ₃ NH-(2-pyridyl) B 1.351 510.3

2-57 CI, H, CI CH ₃ NH-(3-pyridyl) B 1.183 510.3

2-58 CI, H, CI CH ₃ NH-(4-pyridyl) B 1.174 510.3

2-59 CI, H, CI CH ₃ NHCH ₂ -(2-pyrimidyl) B 1.355 525.3

2-60 CI, H, CI CH ₃ NHCH ₂ -(4-pyrimidyl) B 1.331 525.3

2-61 CI, H, CI CH ₃ NH-CeHs B 1.514 509.3

2-62 CI, H, CI CH ₃ N(CH ₃ )-CH ₂ -(2-pyridyl) B 1.274 538.3

N(CH ₂ CH ₃ )-CH ₂ -(2-

2-63 CI, H, CI CH ₃ B 1.305 552.3

pyridyl)

N(CH ₂ CCH)-CH ₂ -(2-

2-64 CI, H, CI CH ₃ B 1.331 562.3

pyridyl)

2-65 CI, H, CI CH ₃ N(CH ₃ )-CH ₂ -(4-thiazolyl) B 1.438 544.3

2-66 CI, H, CI CH ₃ N(CH ₃ )-OCH ₃ B 1.448 477.0

2-67 CI, H, CI CH ₃ NH-CH ₂ -(2-oxazolyl) B 1.363 514.1

2-68 CI, H, CI CH ₃ NH-(3-oxetanyl) B 1.223 489.1

2-69 CI, H, CI CH ₃ pyrrol id in-1-yl B 1.463 487.3

2-70 CI, H, CI CH ₃ azetidin-1-yl B 1.422 474.8

2-71 CI, H, CI CH ₃ NH-cyclobutyl B 1.467 487.0

Ex. R2 R2b, R2c R4 Y HPLC-MS:

Method, Rt (min) & [M+H] ⁺

1 H-NMR

yi)

2-140 CI, CI, CI SCH ₃ NHCH ₂ C(=0)-NHCH ₂ CF ₃ B 1.434 640.0

2-141 CI, CI, CI SCH ₃ NHCH ₂ -(4-thiazolyl) B 1.442 598.0

2-142 CI, CI, CI SCH ₃ NHCH ₂ -(2-thiazolyl) B 1.444 598.0

2-143 CI, CI, CI CH ₃ NHCH ₂ -(2-thiazolyl) B 1.449 566.1

NHCH(CH ₃ )C(=0)-

2-144 CI, H, CI CH ₃ B 1.402 586.2

NHCH ₂ CF ₃

2-145 CI, H, CI CH ₃ NHCH ₂ C(=0)-NHCH ₂ CH ₃ B 1.326 518.2

NHCH ₂ C(=0)-

2-146 CI, H, CI CH ₃ B 1.362 532.2

NHCH(CH ₃ ) ₂

2-147 CI, H, CI CH ₃ NHCH ₂ C(=0)-NHCH ₃ B 1.281 504.2

NHCH ₂ C(=0)-

2-148 CI, H, CI CH ₃ B 1.355 532.3

NHCH ₂ CH ₂ CH ₃

NHCH ₂ -(1 ,3-dioxolan-2-

2-149 CI, H, CI CH ₃ B 1.368 519.2

yi)

2-150 CI, CI, CI CI NHCH ₂ -(2-pyridyl) B 1.245 580.1

2-151 CI, CI, CI CI NHCH ₂ -(2-pyrimidyl) B 1.433 581 .1

2-152 CI, CI, CI CI NHCH ₂ -(2-thiazolyl) B 1.450 586.1

2-153 CI, CI, CI CI NHCH ₂ C(=0)-NHCH ₂ CF ₃ B 1.440 628.1

2-154 CI, CI, CI CI NHCH ₂ CF ₃ B 1.508 571 .1

1 H NMR (400 MHz,CDCI ₃ ): δ 7.8 (s, 1 H), 7.8-7.6 (m, 2H), 7.4

2-155 CI, CI, CI CI NH-(1 , 1-dioxo-thiethan-3- (s, 2H), 7.1 (d, 1 H), 5.0-4.8 (m,

1 H), 4.7-4.6 (m, 2H), 4.2 (d, yi) 1 H), 4.2-4.0 (m, 2H), 3.9 (d, 1 H)

2-156 CI, H, CI CH ₃ OH B 1.419 434.1

2-157 CI, CI, CI CH ₃ OH B 1.472 470.1

2-158 CI, CI, CI SCH ₃ OH B 1.466 500.1

2-159 CI, CI, CI CI OH B 1.477 490.0

2-160 CI, F, CI CH ₃ OC(CH ₃ ) ₃ B 1.678 508.2

2-161 CI, F, CI CH ₃ OH B 1.417 454.0

2-162 CI, F, CI CH ₃ NHCH ₂ C(=0)-NHCH ₂ CF ₃ B 1.373 590.2

NH-(1 , 1-dioxo-thiethan-3-

2-163 CI, F, CI CH ₃ B 1.344 555.2

yi)

2-164 CI, F, CI CH ₃ NHCH ₂ -(2-pyridyl) B 1.190 542.3

2-165 CI, F, CI CH ₃ NHCH ₂ CF ₃ B 1.451 533.3

2-166 CI, F, CI CH ₃ NHCH ₂ -(2-thiazolyl) B 1.391 548.1

2-167 CI, CI, CI OCH ₃ OC(CH ₃ ) ₃ B 1.651 542.2

2-168 CI, CI, CI OCH ₃ OH B 1.424 484.2

2-169 CI, CI, CI OCH ₃ NHCH ₂ C(=0)-NHCH ₂ CF ₃ B 1.434 624.1

NH-(1 , 1-dioxo-thiethan-3-

2-170 CI, CI, CI OCH ₃ B 1.410 589.1

yi)

2-171 CI, CI, CI OCH ₃ NHCH ₂ -(2-pyridyl) B 1.245 574.1 Ex. R2a, R2b, R2c R4 Y HPLC-MS:

Method, Rt (min) & [M+H] ⁺

1 H-NMR

2-172 CI, CI, CI OCH ₃ NHCH ₂ -(2-thiazolyl) B 1.469 580.1

2-173 CI, CI, CI OCH ₃ NHCH ₂ CH ₂ CF ₃ B 1.537 579.1

2-174 CI, H, CF ₃ CH ₃ OC(CH ₃ ) ₃ B 1.657 524.3

2-175 CI, CI, CI H OC(CH ₃ ) ₃ B 1.687 512.1

2-176 CI, H, CF ₃ CH ₃ OH B 1.413 468.2

2-177 CI, CI, CI H OH B 1.435 456.1

2-178 CI, H, CI CH ₃ NHNH-(2-pyridyl) B 1.153 525.2

2-179 CI, H, CI CH ₃ NHN(CH ₃ )-(2-pyridyl) B 1.201 539.2

2-180 CI, H, CI CH ₃ NHCH ₂ CH2CH ₂ CH ₃ B 1.480 489.2

2-181 CI, H, CF ₃ CH ₃ NHCH ₂ C(=0)-NHCH ₂ CF ₃ B 1.358 606.3

2-182 CI, H, CF ₃ CH ₃ NHCH ₂ -(2-pyridyl) B 1.185 558.4

NH-(1 , 1-dioxo-thiethan-3-

2-183 CI, H, CF ₃ CH ₃ B 1.343 571 .2

yi)

2-184 CI, H, CF ₃ CH ₃ NHCH ₂ -(2-thiazolyl) B 1.384 564.2

2-185 CI, H, CF ₃ CH ₃ NHCH ₂ CH ₂ CF ₃ B 1.450 563.2

2-186 CI, CI, CI H NHCH ₂ C(=0)-NHCH ₂ CF ₃ B 1.393 594.2

1 H NMR (400 MHz,CDCI ₃ ): δ

8.1- 7.7 (m, 4H), 7.4 (s, 2H), 6.9-

2-187 CI, CI, CI H NH-(1 , 1-dioxo-thiethan-3- 6.8 (m, 1 H), 5.0-4.8 (m, 1 H),

4.8-4.6 (m, 2H), 4.2 (d, 1 H), yi) 4.2- 4.0 (m, 2H), 3.9 (d, 1 H)

2-188 CI, CI, CI H NHCH ₂ -(2-pyridyl) B 1.21 1 544.1

2-189 CI, CI, CI H NHCH ₂ -(2-thiazolyl) B 1.409 552.1

2-190 CI, CI, CI H NHCH ₂ CH ₂ CF ₃ B 1.470 550.3

2-191 CI, H, CI CH ₃ NHCH ₂ -(6-CF ₃ -pyrid-2-yl) B 1.310 592.3

2-192 CI, H, CI CH ₃ NHNHC(=0)-NHCH ₂ CF ₃ B 1.317 573.3

NH-(2-

2-193 CI, H, CI CH ₃ B 1.335 517.2

oxotetra hyd rof u ran-3-yl)

2-194 CI, H, CI CH ₃ OCH ₂ -(2-pyridyl) B 1.420 525.3

NH-[2-oxo-1 -(2,2,2-

2-195 CI, H, CI CH ₃ trifluoroethyl)pyrrolidin-3- B 1.388 598.2

yi]

2-196 CI, H, CI CH ₃ OCH ₂ CH ₂ CF ₃ B 1.593 530.2

2-197 CI, H, CI CH ₃ NH-(2-pyrazinyl) B 1.421 51 1 .2

2-198 CI, H, CI CH ₃ NH ₂ B 1.310 433.2

2-199 CI, H, CI CH ₃ NHCH=NOCH ₃ B 1.459 490.3

2-200 CI, H, CI CH ₃ NH-(1-acetylazetidin-3-yl) B 1.284 530.3

NH-(1-methyl-2-oxo-

2-201 CI, H, CI CH ₃ B 1.296 530.3

pyrrolidin-3-yl)

2-202 CI, H, CI CH ₃ NHCH ₂ CH ₂ OH A 3.705 477.0

2-203 CI, H, CI CH ₃ NHCH ₂ CH ₂ OCH ₂ CH ₃ A 4.141 505.0

2-204 CI, H, CI CH ₃ NHCH ₂ CH ₂ OCH ₂ CF ₃ A 4.277 559.0

2-205 CI, H, CI CH ₃ NH2 B 1.398 434.2

2-206 CI, H, CI CH ₃ NHCH ₂ CH ₂ OCH ₃ B 1.353 491 .4

2-207 CI, H, CI CH ₃ NHCH(CH ₃ )CH ₂ OCH ₃ B 1.393 505.3 Ex. R2a, R2b, R2c R4 Y HPLC-MS:

Method, Rt (min) & [M+H] ⁺ or

1 H-NMR

2-208 CI, H, CI CH ₃ NHCH ₂ CH2CH ₂ CF ₃ B 1.459 543.0

2-209 CI, H, CI CH ₃ NHCH ₂ CF ₂ CF ₃ B 1.494 565.2

2-210 CI, H, CI CH ₃ NHCH ₂ CH ₂ SCF ₃ B 1.487 561 .4

2-21 1 CI, H, CI CH ₃ NHCH ₂ CH ₂ OCF ₃ B 1.447 545.3

N(CH ₃ )-CH ₂ C(=0)-

2-212 CI, H, CI CH ₃ B 1.377 586.4

NHCH ₂ CF ₃

2-213 CI, H, CI SCH ₃ NHCH ₂ CF ₃ B 1.444 547.1

2-214 CI, H, CI SCH ₃ pyrrol id in-1-yl B 1.463 519.2

2-215 CI, H, CI SCH ₃ NHCH ₂ -(2-pyridyl) B 1.200 556.2

2-216 CI, H, CI SCH ₃ NHCH ₂ C(=0)-NHCH ₂ CF ₃ B 1.369 604.2

2-217 CI, H, CI SCH ₃ NHCH ₂ -(2-pyrimidyl) B 1.346 557.2

2-218 CI, H, CI SCH ₃ NHCH ₂ -(2-thiazolyl) B 1.371 564.0

NH-(1 , 1-dioxo-thiethan-3-

2-219 CI, H, CI SCH ₃ B 1.331 569.2 yi)

2-220 CI, H, CI SCH ₃ NH-(3-thiethanyl) B 1.425 538.9

NHCH ₂ C(=0)-

2-221 CI, H, CI CH ₃ B 1.319 528.4

NHCH ₂ CCH

NHCH ₂ C(=0)-N(CH ₃ )-

2-222 CI, H, CI CH ₃ B 1.402 586.4

CH ₂ CF ₃

2-223 CI, H, CI CH ₃ NH-(4-CF ₃ -thiazol-2-yl) B 1.407 584.4

2-224 CI, CI, CI CH ₃ NHCH ₂ -(2-pyrimidyl) B 1.397 561 .1

2-225 CI, F, CI CH ₃ NHCH ₂ -(2-pyrimidyl) B 1.340 543.2

2-226 CI, H, CI CH ₃ NHCH ₂ -(5-CI-pyrid-2-yl) B 1.400 560.1

2-227 CI, H, CF ₃ CH ₃ NHCH ₂ -(2-pyrimidyl) B 1.382 559.2

2-228 CI, H, CI CH ₃ NHNH-(2-pyrimidyl) B 1.341 526.2

2-229 CI, H, CI CH ₃ NH-(5-pyrimidyl) B 1.382 51 1 .0

2-230 CI, H, CI CH ₃ NH-(2-pyrimidyl) B 1.349 51 1.0

2-231 CI, H, CI CH ₃ NHCH=NOCH ₂ CF ₃ B 1.527 557.9

NHNHC(=0)-

2-232 CI, H, CI CH ₃ B 1.318 555.4

NHCH ₂ CHF ₂

2-233 CI, H, CI CH ₃ NHCH ₂ C(=0)-NHCH ₂ CN B 1.300 529.3

NH-(3-oxo-isoxazolidin-4-

2-234 CI, H, CI CH ₃ B 1.282 519.9 yi)

C.3 Compound examples 3 Compound examples 3-1 to 3-28 correspond to compounds of formula C.3:

wherein R ^2a , R ^2b , R ^2c , R ⁴ , R ⁵ and R ⁶ of each synthesized compound is defined row of table C.3 below.

The compounds were synthesized in analogy to Synthesis Example S.3.

Table C.3

C.4 Compound examples 4 Compound example 4-1 corresponds to compounds of formula C.4:

wherein R ^2a , R ^2b , R ^2c , R ⁴ , and A ⁴ of each synthesized compound is defined in one row of table C.4 below.

Compound 4-1 was synthesized in analogy to Synthesis Example S.2. The starting material (2-(1 ,2,4-triazoM -yl)-5-[(Z)-4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-2- enoyl]benzonitrile) was prepared in analogy to the method described in EP-A-2172462.

Table C.4

C.5 Compound examples 5

Compound examples 5-1 to 5-15 correspond to compounds of formula C.5:

wherein R ^2a , R ^2b , R ^2c , R ^3a , G ¹ , R ^4a , R ^4b , and Y of each synthesized compound is defined in one row of table C.5 below.

Compounds 5-1 to 5-3 were synthesized in analogy to Synthesis Example S.4.

Compounds 5-4 to 5-15 were synthesized in analogy to Synthesis Example S.2.

Table C.5

C.6 Compound examples 6 (Intermediates)

Intermediates 6-1 to 6-7 correspond to compounds of formula C.6:

wherein R ^2a , R ^2b , R ^2c , R ⁴ , and YY of each synthesized compound is defined in one row of table C.6 below.

Synthesis Example S.1

1 -[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isot hiazol-3-yl]-2-methyl- phenyl]methyleneamino]-3-ethyl-urea

(Compound example 1 -5; compound of formula IA, wherein R ^2a and R ^2c are CI, R ² is H, R ⁴ is methyl and A is A ¹ = -CH(=N-NH-C(=0)-NH-CH ₂ CH ₃ ). Step 1 : 1 -(4-Bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-3-sulfanyl -butan-1 -one

1 -(4-Bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)but-2-en-1 -one (21 .5 g, 4:1 -mixture of E/Z-isomers) in CH ₂ CI ₂ (400 mL) was treated with triethylamine (68 mL). At 0°C, gaseous hydrogen sulfide (H2S) was bubbled through the solution for 10 min. The mixture was stirred for another 20 min at 0°C, and then diluted with CH2CI2 (300 mL). The organic layer was washed with 6% aqueous hydrochloric acid (300 mL), dried (MgS0 ₄ ), filtered, and concentrated.

The product was obtained as a yellowish oil (23.1 g, 99.7%).

HPLC-MS (method B): 1 .557 min, M = 472.90.

Step 2: 3-(4-Bromo-3-methyl-phenyl)-5-(3,5-dichlorophenyl)-5-methyl- 4H-isothiazole

At -15°C, the product of step 1 (23 g) in CH2CI2 (400 mL) was treated with triethylamine (27.1 mL) and with a solution of hydroxylamine-O-sulfonic acid ("HOSA", 6.23 g) in water (10 mL). The reaction was warmed to 0°C and stirred at 0°C for 45 min, and then diluted with CH2CI2 (400 mL). The organic layer was washed with saturated aqueous NH ₄ CI solution (3x), dried (MgS0 ₄ ), and filtered. To the obtained solution, acid washed molecular sieves (AW 300, 150 g) were added and the mixture was stirred vigorously for 90 min at room temperature. Then, the molecular sieves were filtered off, and the filtrate concentrated to afford a residue that was purified by flash chromatography on silica gel (ethyl acetate/cyclohexane). The obtained pale yellow solid (19.5 g) was ti- turated with hexanes (3x) to afford the product as a white solid (15.6g, 68%).

HPLC-MS (method B): 1 .697 min, M = 469.90.

Step 3: Methyl 4-[5-(3,5-dichlorophenyl)-5-methyl-4H-isothiazol-3-yl]-2-met hyl- benzoate

The product of step 2 (14.6 g) in methanol/THF (63 mL/6 mL) was treated with [1 ,1 - bis(diphenylphosphino)ferrocene]dichloropalladium(ll) ("Pd(dppf)Cl2", 5.08 g),

Pd(OAc)2 (0.42 g), NaOAc (3.7 g). The reaction was subsequently pressurized twice with N2 (3.5 bar) and three times with carbon monoxide (5 bar). Then, the mixture was pressurized with carbon monoxide (7.5 bar) and heated at 80°C (internal temperature) for 13 h. Thereby, the carbon monoxide pressure was adjusted several times back to 7.5 bar. Then, the reaction was cooled to room temperature, filtered over celite (CH2CI2) and subsequently filtered over a plug of silica gel. The product was obtained as a pale yellow foam (13.1 g, 89%).

HPLC-MS (method A): 3.974 min, M = 566.00.

Step 4: [4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol -3-yl]-2-methyl- phenyl]methanol

To a solution of the product of step 3 (4.9 g) in CH2CI2 (100 ml.) at 0 °C was added a solution of DIBAL-H in toluene (1 .5 M, 16 ml_). The resulting solution was stirred at 0 °C for 90 min and quenched by adding MeOH (10 ml_). A saturated solution of Ro- chelle's salt (potassium sodium tartrate, CAS 304-59-6) (100 ml.) was added, followed by vigorous stirring at r.t. for 2 h. Then, CH2CI2 (300 ml.) was added, and the organic layer was washed with water, dried (Na2S0 ₄ ), filtered, and concentrated to afford a residue that was purified by flash chromatography on silica gel (ethyl acetate/hexanes). The product was obtained as pale yellow solid (3.45 g, 75%).

HPLC-MS (methode A): 4.390 min, M = 419.95. Step 5: 4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol- 3-yl]-2-methyl- benzaldehyde

To a solution of the product of step 1 (1 g) in CH ₂ CI ₂ (40 ml.) at r.t. was added Dess- Martin-Periodane (CAS 87413-09-0) (1.1 1 g). The reaction was stirred overnight, fil- tered and concentrated. The residue was purified by flash chromatography on silica gel (ethyl acetate/cyclohexane). The product was obtained as a viscous oil (0.81 g, 81 %).

HPLC-MS (method A): 4.036 min, M = 417.90. Step 6: 1 -[(E)-[4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isot hiazol-3-yl]-2-methyl- phenyl]methyleneamino]-3-ethyl-urea

A solution of the product of step 2 (0.15 g) and 1 -ammonium-3-ethyl urea hydrochloride (60 mg) in EtOH (4 mL) and acetic acid (0.14 mL) was stirred at 70 °C overnight, and concentrated. The residue was purified by flash chromatography on silica gel (ethyl acetate/cyclohexane). The product was obtained as a pale yellow foam (0.10 g, 55%).

HPLC-MS (method B): 1.484 min, M = 505.0. Synthesis Example S.2

4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4H-isothiazol-3- yl]-2-methyl-N-[2-oxo-2- (2,2,2-trifluoroethylamino)ethyl]benzamide

(Compound example 2-1 ; compound of formula IA, wherein R ^2a and R ^2c are CI, R ² is H, R ⁴ is methyl and A is A ² = -C(=0)-NH-CH ₂ -C(=0)-NH-CH ₂ CF ₃ )

Step 1 : 4-[5-(3,5-dichlorophenyl)-5-methyl-4H-isothiazol-3-yl]-2-met hyl-benzoic acid To a solution of methyl 4-[5-(3,5-dichlorophenyl)-5-methyl-4H-isothiazol-3-yl]-2-met hyl- benzoate (= the product of step 3 of example 1 ) (2.4 g) in THF (50 mL) was added a solution of LiOH (0.51 g) in water (50 mL). The reaction was stirred for 16 h at room temperature, then diluted with water (300 mL) and washed with CH2CI2 (3x). The aqueous phase was acidified with aqueous 1 M HCI to pH 1 -2 and extracted with CH2CI2 (3x). The combined organic layers were washed with water, dried (Na2S0 ₄ ), filtered, and concentrated. The product was obtained as a pale yellow solid (2.24 g, 96%).

HPLC-MS (method A): 4.458 min, M = 433.95. Step 2: 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4H-isothiazol-3- yl]-2-methyl-N-[2- oxo-2-(2,2,2-trifluoroethylamino)ethyl]benzamide

To a solution of the product of step 1 (2.2 g), [2-oxo-2-(2,2,2- trifluoroethylamino)ethyl]ammonium chloride (1.22 g) and bromotripyrrolidinophospho- nium hexafluorophosphate ("PyBroP", 2.95 g) in CH2CI2 (100 mL) at room temperature was added A/,A/-diisopropylethylamine (3.53 mL). The reaction was stirred at room temperature for 16 h, then concentrated and redissolved in ethyl acetate (200 mL). The organic layer was washed with 5% aqueous HCI (2x) and 5% aqueous K2CO3 (2x), dried (Na2S0 ₄ ), filtered, and concentrated to afford a residue that was purified by flash chromatography on silica gel (ethyl acetate/cyclohexane). The product was obtained as amorphous white foam (2.45 g, 84%).

HPLC-MS (method A): 4.045 min, M = 572.00. Synthesis Example S.3

N-[[4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isothia zol-3-yl]-2-methyl- phenyl]methyl]-N-ethyl-2-ethylsulfanyl-acetamide

(Compound example 3-3; compound of formula IA, wherein R ^2a and R ^2c are CI, R ² is H, R ⁴ is methyl and A is A ³ = -CH ₂ -N(CH2CH3)-C(=0)-CH2SCH ₂ CH3). Step 1 : N-[[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothia zol-3-yl]-2-methyl- phenyl]methyl]ethanamine To a solution of [4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol -3-yl]-2- methyl-phenyl]methanol (i.e. the product of example 1 , step 4) (1 .5 g) in CH2CI2 (50 mL) was added triethylamine (0.75 mL) and methansulfonylchloride (0.63 g) at r.t.. The reaction was stirred at r.t. overnight, then diluted with ethyl acetate (200 mL), and washed with water (3x), dried (Na2S0 ₄ ), filtered, and concentrated to afford the crude mesylate (1.19 g) that was re-dissolved in acetonitrile (30 mL) and treated with a solution of ethylamine in THF (2 M, 8.8 mL). The reaction was stirred overnight at r.t.. The residue was taken up in ethyl acetate and washed with 5% aqueous potassium carbonate solution (3x), dried (Na2S0 ₄ ), filtered, and concentrated to afford the product as a solid (0.98 g, 59%).

HPLC-MS (method B): 1.139 min, M = 447.3.

Step 2: N-[[4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isothia zol-3-yl]-2-methyl- phenyl]methyl]-N-ethyl-2-ethylsulfanyl-acetamide

To a solution of the product of step 1 (0.30 g), (ethylthio)acetic acid (0.10 g) and bro- motripyrrolidinophosphonium hexafluorophosphate ("PyBroP", 0.39 g) in CH2CI2 (20 mL) at r.t. was added A/,A/-diisopropylethylamine (0.47 mL). The reaction was stirred at r.t. for 16 h, then concentrated to afford a residue that was purified by flash chromatog- raphy on silica gel (ethyl acetate/cyclohexane). The product was obtained as amorphous foam (330 mg, 90%).

HPLC-MS (method A): 4.639 min, M = 549.00. Synthesis Example S.4

4-[5-(3,5-dichlorophenyl)-4-fluoro-5-(trifluoromethyl)-4H-is othiazol-3-yl]-2-methyl-N-[2- oxo-2-(2,2,2-trifluoroethylamino)ethyl]benzamide

(Compound example 5-1 ; compound of formula C.5, wherein R ^2a and R ^2c are CI, R ^2b is H, R ^3a is F, G is CH, R ^4a is H, R ^4b is methyl and Y is -NHCH ₂ -C(=0)-NHCH ₂ CF ₃ ).

Step 1 : tert-butyl 4-[5-(3,5-dichlorophenyl)-4-fluoro-5-(trifluoromethyl)-4H-is othiazol-3- yl]-2-methyl-benzoate To a solution of [tert-butyl 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol- 3- yl]-2-methyl-benzoate (prepared from "tert-butyl 4-[(Z)-3-(3,5-dichlorophenyl)-4,4,4- trifluoro-but-2-enoyl]-2-methyl-benzoate" in analogy to Synthesis Example S.1 , step 1 and step 2) (2.55 g) in THF (40 mL) under nitrogen at -78°C was added LiHMDS (5.7 mL, 1 M solution in THF) and the mixture was stirred for 1 .5 h at -78°C. Then,

/V-fluorobenzenesulfonimide ("NFSI", 2.1 g) was added at -78°C in one portion and the mixture was stirred at -78°C for another 2 h. Then, the reaction was quenched with saturated aqueous NH4CI solution. EtOAc was added and the organic layer was washed with water (3x), dried (Na2S0 ₄ ), filtered, and concentrated to afford a residue that was purified by flash chromatography on silica gel (ethyl acetate/cyclohexane). The product was obtained as yellow oil (1 .65 g, 62%).

1 H NMR (400 MHz,CDCI ₃ , signals of major diastereomer): δ 7.9 (d, 1 H), 7.7-7.6 (m, 2H), 7.5 (s, 1 H), 7.4 (s, 2H), 6.4 (d, 1 H, CHF), 2.6 (s, 3H), 1 .6 (s, 9H).

Step 2: 4-[5-(3,5-dichlorophenyl)-4-fluoro-5-(trifluoromethyl)-4H-is othiazol-3-yl]-2- methyl-benzoic acid

To a solution of the product of step 1 (0.36 g) in CH2CI2 (20 mL) at 0°C was added tri- fluoroacetic acid ("TFA", 10 mL), and the mixture was stirred at r.t. overnight. Then, the reaction was concentrated, azeotroped with CH2CI2 (5x) and triturated with petroleum ether / EtOAc (40:1 ) to obtain the product as a pale yellow solid (0.28 g, 87%).

1 H NMR (400 MHz, d6-DMSO, signals of major diastereomer): δ 8.0-7.8 (m, 4H), 7.7 (s, 2H), 7.5 (d, 1 H, CHF), 2.6 (s, 3H).

Step 3: 4-[5-(3,5-dichlorophenyl)-4-fluoro-5-(trifluoromethyl)-4H-is othiazol-3-yl]-2- methyl-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]benzamide To a solution of the product of step 2 (0.25 g) in toluene/CH ₂ Cl2 (1 :1 , 20 mL) was added A/,A/-dimethylformamide ("DMF", 1 drop) and oxalyl chloride (0.14 mL). The reaction was stirred overnight, concentrated, and azeotroped with CH2CI2 (5x). The obtained residue (0.26 g) was dissolved in THF (30 mL) and added to a solution of 2-amino-/V- (2,2,2-trifluoroethyl)acetamide hydrochloride and triethylamine (0.22 g) in THF (30 mL). The reaction was stirred overnight, filtered and concentrated to afford a residue that was purified by flash chromatography on silica gel (ethyl acetate/cyclohexane). The product was obtained as amorphous foam (0.13 g, 40%). HPLC-MS (method B): 1.364 min, M = 590.2.

II. Evaluation of pesticidal activity:

The activity of the compounds of formula I of the present invention can be

demonstrated and evaluated by the following biological test. B.1 Cotton aphid (Aphis gossypii)

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 at the cotyledon stage were infested with aphids prior to treatment by placing a heavily infested leaf from the main aphid colony on top of each cotyledon. Aphids were allowed to transfer overnight to accomplish an infestation of 80-100 aphids per plant and the host leaf was removed. The infested plants were then sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood, removed from the sprayer, and then maintained in a growth room under fluorescent lighting in a 24-hr photoperiod at 25°C and 20-40% relative humidity. Aphid mortality on the treated plants, relative to mortality on untreated control plants, was determined after 5 days.

In this test, the compounds 2-4, 2-10, 2-12, 2-15, 2-19, 2-26, 2-27, 2-28, 2-29, 2-31 , 2- 32, 2-35, 2-37, 2-38, 2-42, 2-43, 2-47, 2-48, 2-49, 2-50, 2-53, 2-57, 2-59, 2-62, 2-63, 2- 65, 2-68, 2-71 , 2-72, 2-73, 2-74, 2-75, 2-82, 2-83, 2-86, 2-88, 2-93, 2-99, 2-109, 2-1 18, 2-137, 2-138, 2-142, 2-143, 2-145, 2-149, 2-150, 2-151 , 2-152, 2-153, 2-162, 2-163, 2- 164, 2-166, 2-171 , 2-178, 2-182, 2-183, 2-185, 2-195, 2-199, 3-1 1 , and 3-12 at 100 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.2 Cowpea aphid (Aphis craccivora)

Potted cowpea plants colonized with approximately 100 - 150 aphids of various stages were sprayed after the pest population had been recorded. Population reduction was assessed after 24, 72, and 120 hours. In this test, the compounds 1 -13, 2-1 , 2-2, 2-4, 2-8, 2-9, 2-10,2-11,2-12, 2-15, 2-19, 2- 26, 2-28, 2-32, 2-33, 2-34, 2-35, 2-36, 2-38, 2-47, 2-51, 2-54, 2-55, 2-59, 2-69, 2-137, 2-142, 2-150, 2-151, 2-152, 2-162, 2-164, 2-165, 2-166, 2-178, 2-180, 2-181, 2-182, 2-

184, 2-185, 2-197, 2-199, 2-200, 2-215, 2-217, 2-218, 2-220, 2-223, 2-224, 2-225, 2- 227, 3-1,3-2, 3-8, 3-9, 3-11, 3-12, 3-21, 3-23, 4-1, and 5-2 at 500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.3 Diamond back moth (Plutella xylostella) Leaves of Chinese cabbage were dipped in test solution and air-dried. Treated leaves were placed in petri dished lined with moist filter paper. Mortality was recorded 24, 72, and 120 hours after treatment.

In this test, the compounds 1-1, 1-2, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 1-15, 2-1 , 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11,2-12,2-13, 2-15, 2-18, 2-19, 2-20, 2-21, 2-22, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-34, 2-35, 2-36, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-50, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71 , 2-72, 2-73, 2-74, 2-75, 2-76, 2-77, 2-78, 2-80, 2-81 , 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91 , 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2- 111, 2-112, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-123, 2-124, 2- 125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2- 137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143, 2-144, 2-145, 2-146, 2-147, 2-148, 2- 149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-162, 2-163, 2-164, 2-165, 2-166, 2- 169, 2-170, 2-171, 2-172, 2-173, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-

185, 2-186, 2-188, 2-189, 2-190, 2-191, 2-192, 2-193, 2-194, 2-195, 2-197, 2-198, 2- 199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-211, 2- 212, 2-213, 2-214, 2-215, 2-216, 2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223, 2- 224, 2-225, 2-226, 2-227, 3-1 , 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11 , 3-12, 3- 13, 3-14, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-25, 3-26, 3-27, 4-1,5-1, 5-2, 5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls. B.4 Green Peach Aphid (Myzus persicae)

For evaluating control of green peach aphid (Myzus persicae) through systemic means the test unit consisted of 96-well-microtiter plates containing liquid artificial diet under an artificial membrane.

The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were pipetted into the aphid diet, using a custom built pipetter, at two replications. After application, 5- 8 adult aphids were placed on the artificial membrane inside the microtiter plate wells. The aphids were then allowed to suck on the treated aphid diet and incubated at about 23 + 1°C and about 50 + 5 % relative humidity for 3 days. Aphid mortality and fecundity was then visually assessed.

In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-7, 1-8, 1-9, 1-10, 1-12, 1-13, 1-14, 1 -15, 2-1 , 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11,2-12,2-13, 2-15, 2-18, 2-19, 2-20, 2-21, 2-23, 2-24, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-35, 2-37, 2-38, 2-39, 2-40, 2-41 , 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-51 , 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61 , 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71 , 2-72, 2-73, 2-74, 2-75, 2-76, 2-77, 2-81 , 2-82, 2-83, 2-84, 2-85, 2-86, 2-87,

2- 88, 2-89, 2-90, 2-91 , 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101 , 2- 102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-110, 2-111, 2-112, 2-113, 2- 114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-123, 2-124, 2-125, 2-126, 2- 127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2- 139, 2-140, 2-141, 2-142, 2-143, 2-145, 2-146, 2-147, 2-148, 2-149, 2-150, 2-151, 2- 152, 2-153, 2-154, 2-155, 2-159, 2-160, 2-162, 2-163, 2-164, 2-165, 2-166, 2-167, 2- 168, 2-169, 2-170, 2-171, 2-172, 2-173, 2-177, 2-178, 2-179, 2-180, 2-181, 2-182, 2- 183, 2-184, 2-185, 2-186, 2-187, 2-188, 2-189, 2-190, 2-191, 2-192, 2-193, 2-194, 2- 195, 2-196, 2-197, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-206, 2-207, 2-208, 2- 209, 2-210, 2-211, 2-215, 2-216, 2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223, 2- 224, 2-225, 2-226, 2-227, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11,3-12, 3-13, 3-14,

3- 16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-25, 3-26, 3-27, 3-28, 4-1, 5-1, 5- 2, 5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.5 Mediterranean fruitfly (Ceratitis capitata)

For evaluating control of Mediterranean fruitfly (Ceratitis capitata) the test unit consist- ed of microtiter plates containing an insect diet and 50-80 C. capitata eggs.

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

After application, microtiter plates were incubated at about 28 ± 1°C and about 80 ± 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed.

In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12,

1- 13, 1-14, 2-1,2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-15, 2-18,

2- 19, 2-20, 2-21, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-34, 2-35, 2-37, 2-38, 2-39, 2-40, 2-41 , 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-51 , 2-52, 2-53,

2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61 , 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71 , 2-72, 2-73, 2-74, 2-75, 2-76, 2-77, 2-78, 2-80, 2-81 , 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91 , 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101 , 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-1 1 1 , 2-1 12, 2-1 14, 2- 1 15, 2-1 16, 2-1 17, 2-1 18, 2-1 19, 2-120, 2-121 , 2-123, 2-124, 2-125, 2-126, 2-127, 2- 128, 2-129, 2-130, 2-131 , 2-132, 2-133, 2-135, 2-138, 2-140, 2-141 , 2-142, 2-143, 2- 146, 2-147, 2-148, 2-149, 2-150, 2-151 , 2-152, 2-153, 2-154, 2-155, 2-162, 2-163, 2- 164, 2-165, 2-166, 2-169, 2-170, 2-171 , 2-172, 2-178, 2-179, 2-180, 2-181 , 2-182, 2- 183, 2-184, 2-185, 2-186, 2-187, 2-188, 2-189, 2-190, 2-191 , 2-192, 2-194, 2-195, 2- 197, 2-198, 2-199, 2-200, 2-201 , 2-202, 2-203, 2-206, 2-207, 2-209, 2-212, 2-215, 2- 216, 2-217, 2-218, 2-220, 2-221 , 2-222, 2-223, 2-224, 2-225, 2-226, 2-227, 3-3, 3-4, 3- 5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-1 1 , 3-12, 3-13, 3-14, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21 , 3- 22, 3-23, 3-24, 3-25, 3-26, 3-27, 3-28, 4-1 , 5-1 , 5-2, 5-3, 5-4, and 5-7 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.6 Orchid thrips (dichro moth rips corbetti)

Dichromothrips corbetti adults used for bioassay were obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the test compound was diluted to a concentration of 500 ppm (wt compound: vol diluent) in a 1 :1 mixture of acetone:water (vohvol), plus 0.01 % vol/vol Kinetic ^® surfactant.

Thrips potency of each compound was evaluated by using a floral-immersion technique. Plastic petri dishes were used as test arenas. All petals of individual, intact orchid flowers were dipped into treatment solution and allowed to dry. Treated flowers were placed into individual petri dishes along with 10 - 15 adult thrips. The petri dishes were then covered with lids. All test arenas were held under continuous light and a temperature of about 28°C for duration of the assay. After 4 days, the numbers of live thrips were counted on each flower, and along inner walls of each petri dish. The level of thrips mortality was extrapolated from pre-treatment thrips numbers. In this test, the compounds 1 -1 , 1 -2, 1 -5, 1 -7, 1 -8, 1 -9, 1 -10, 1 -13 2-1 , 2-2, 2-3, 2-4, 2- 5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-1 1 , 2-12, 2-13, 2-15, 2-18, 2-19, 2-20, 2-21 , 2-22, 2-23, 2- 26, 2-27, 2-28, 2-29, 2-30, 2-31 , 2-33, 2-34, 2-35, 2-37, 2-38, 2-39, 2-40, 2-41 , 2-42, 2- 43, 2-45, 2-46, 2-47, 2-48, 2-49, 2-50, 2-51 , 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2- 59, 2-60, 2-61 , 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71 , 2-72, 2-73, 2- 74, 2-75, 2-76, 2-77, 2-78, 2-80, 2-81 , 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2- 90, 2-91 , 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101 , 2-102, 2-103, 2- 104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-1 1 1 , 2-1 12, 2-1 13, 2-1 14, 2-1 15, 2-1 16, 2- 1 17, 2-1 18, 2-1 19, 2-120, 2-121 , 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2- 130, 2-131 , 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141 , 2- 142, 2-143, 2-144, 2-145, 2-146, 2-147, 2-148, 2-149, 2-150, 2-151 , 2-152, 2-153, 2- 154, 2-155, 2-162, 2-163, 2-164, 2-165, 2-166, 2-169, 2-170, 2-171 , 2-172, 2-173, 2- 178, 2-179, 2-180, 2-181 , 2-182, 2-183, 2-184, 2-185, 2-186, 2-187, 2-188, 2-189, 2- 190, 2-192, 2-193, 2-195, 2-197, 2-198, 2-199, 2-200, 2-201 , 2-202, 2-203, 2-204, 2- 206, 2-207, 2-208, 2-209, 2-210, 2-21 1 , 2-212, 2-213, 2-214, 2-215, 2-216, 2-217, 2- 218, 2-219, 2-220, 2-221 , 2-222, 2-223, 2-224, 2-225, 2-226, 2-227, 3-1 , 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-1 1 , 3-12, 3-13, 3-14, 3-15, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21 , 3-22, 3-23, 3-24, 3-25, 3-26, 3-27, 4-1 , 5-1 , 5-2, 5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.7 Rice green leafhopper (Nephotettix virescens)

Rice seedlings were cleaned and washed 24 hours before spraying. The active compounds were formulated in 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 1 -7, 2-1 , 2-2, 2-4, 2-5, 2-6, 2-9, 2-10, 2-1 1 , 2-13, 2-15, 2- 19, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31 , 2-32, 2-33, 2-35, 2-37, 2-38, 2-40, 2-41 , 2- 42, 2-43, 2-45, 2-47, 2-48, 2-49, 2-50, 2-51 , 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2- 59, 2-60, 2-61 , 2-62, 2-63, 2-64, 2-67, 2-68, 2-69, 2-70, 2-71 , 2-72, 2-73, 2-74, 2-81 , 2- 82, 2-83, 2-84, 2-85, 2-86, 2-88, 2-89, 2-91 , 2-93, 2-94, 2-95, 2-97, 2-99, 2-100, 2-101 , 2-102, 2-104, 2-107, 2-108, 2-109, 2-1 12, 2-1 14, 2-1 15, 2-1 16, 2-1 18, 2-1 19, 2-120, 2- 121 , 2-124, 2-126, 2-127, 2-128, 2-129, 2-131 , 2-132, 2-133, 2-134, 2-135, 2-136, 2- 137, 2-138, 2-139, 2-140, 2-141 , 2-142, 2-143, 2-145, 2-146, 2-147, 2-148, 2-149, 2- 150, 2-151 , 2-152, 2-153, 2-154, 2-155, 2-162, 2-163, 2-164, 2-165, 2-166, 2-170, 2- 178, 2-179, 2-180, 2-181 , 2-182, 2-183, 2-184, 2-185, 2-193, 2-195, 2-197, 2-199, 2- 200, 2-201 , 2-203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-21 1 , 2-212, 2-213, 2- 214, 2-215, 2-216, 2-217, 2-218, 2-219, 2-220, 2-222, 2-224, 2-225, 2-226, 2-227, 3-3, 3-4, 3-6, 3-7, 3-8, 3-10, 3-1 1 , 3-12, 3-17, 3-18, 3-19, 3-21 , 3-23, 3-24, 3-25, 3-26, 4-1 , 5-2, and 5-3 at 500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.8 Silverleaf whitefly (bemisia argentifolii)

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 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 about 10 to 12 whitefly adults (approximately 3-5 days old) were introduced. The insects were collected using an aspirator and a nontoxic Tygon® tubing 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. Test plants were maintained in a growth room at about 25°C and about 20-40% relative humidity for 3 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment, compared to untreated control plants.

In this test, the compounds 1 -7, 1 -9, 1 -10, 2-2, 2-3, 2-4, 2-5, 2-10, 2-1 1 , 2-12, 2-13, 2- 15, 2-23, 2-26, 2-28, 2-29, 2-31 , 2-33, 2-35, 2-37, 2-38, 2-39, 2-40, 2-41 , 2-42, 2-43, 2- 47, 2-48, 2-49, 2-50, 2-53, 2-57, 2-58, 2-59, 2-62, 2-63, 2-65, 2-66, 2-67, 2-68, 2-71 , 2- 72, 2-73, 2-74, 2-75, 2-77, 2-81 , 2-82, 2-83, 2-84, 2-86, 2-87, 2-88, 2-90, 2-91 , 2-92, 2- 93, 2-95, 2-96, 2-99, 2-100, 2-109, 2-1 10, 2-1 14, 2-1 15, 2-121 , 2-123, 2-128, 2-130, 2- 134, 2-136, 2-137, 2-138, 2-139, 2-140, 2-142, 2-143, 2-145, 2-146, 2-148, 2-149, 2- 150, 2-151 , 2-152, 2-153, 2-154, 2-155, 2-162, 2-163, 2-164, 2-165, 2-166, 2-169, 2- 171 , 2-172, 2-173, 2-178, 2-179, 2-181 , 2-182, 2-183, 2-185, 2-186, 2-188, 2-189, 2- 190, 2-195, 2-199, 3-1 , 3-4, 3-6, 3-7, 3-9, 3-10, 3-1 1 , 3-12, and 3-19 at 100 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls. B.9 Southern armyworm (Spodoptera eridania)

The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01 % (v/v).

Lima bean plants (variety Sieva) were grown 2 plants to a pot and selected for treatment at the 1 ^st true leaf stage. Test solutions were sprayed onto the foliage by an au- tomated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into perforated plastic bags with a zip closure. About 10 to 1 1 armyworm larvae were placed into the bag and the bags zipped closed. Test plants were maintained in a growth room at about 25°C and about 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to pre- vent trapping of heat inside the bags. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants.

In this test, the compounds 1-1, 1-2, 1-5, 1-7, 1-8, 1-9, 1-10, 1-11, 1-13, 1-14,2-1,2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11,2-12,2-13, 2-15, 2-18, 2-19, 2-20, 2-21 , 2- 23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31 , 2-32, 2-33, 2-35, 2-37, 2-38, 2-39, 2-40, 2-41 , 2- 42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-50, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2- 57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2- 72, 2-73, 2-74, 2-75, 2-76, 2-77, 2-81 , 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2- 90, 2-91, 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101, 2-102, 2-103, 2- 104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-110, 2-112, 2-114, 2-115, 2-116, 2-117, 2- 118, 2-119, 2-120, 2-121, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2- 131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2- 143, 2-144, 2-145, 2-146, 2-147, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2- 155, 2-162, 2-163, 2-164, 2-165, 2-166, 2-169, 2-170, 2-171 , 2-172, 2-173, 2-178, 2- 179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-187, 2-188, 2-189, 2-190, 2- 191, 2-192, 2-193, 2-195, 2-197, 2-198, 2-199, 2-200, 2-202, 2-203, 2-204, 2-206, 2- 207, 2-208, 2-209, 2-210, 2-212, 2-214, 2-216, 2-221, 2-222, 2-224, 2-225, 2-226, 2- 227, 3-1,3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-13, 3-17, 3-18, 3-19, 3-20, 3-21 , 3-22, 3-23, 3-24, 3-25, 3-26, 3-27, 4-1 , 5-2, 5-3, 5-6 and 5-7 at 1 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.10 Vetch aphid (Megoura viciae) For evaluating control of vetch aphid (Megoura viciae) through contact or systemic means the test unit consisted of 24-well-microtiter plates containing broad bean leaf disks.

The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the leaf disks at 2.5 μΙ, using a custom built micro atomizer, at two replications.

After application, the leaf disks were air-dried and 5-8 adult aphids placed on the leaf disks inside the microtiter plate wells. The aphids were then allowed to suck on the treated leaf disks and incubated at about 23 ± 1°C and about 50 ± 5 % relative humidity for 5 days. Aphid mortality and fecundity was then visually assessed.

In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-7, 1-8, 1-9, 1-10, 1-12, 1-13, 1-15, 2-1,2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11,2-12, 2-13, 2-15, 2-19, 2-20, 2-21, 2-23, 2-24, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31 , 2-32, 2-33, 2-35, 2-36, 2-37, 2-38, 2-39, 2-40, 2-41 , 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-51 , 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61 , 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73, 2-74, 2-75, 2-77, 2-79, 2-81, 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91 , 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101 , 2-102, 2- 104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-110, 2-111, 2-112, 2-114, 2-115, 2-116, 2- 117, 2-118, 2-119, 2-120, 2-121, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2- 130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2- 142, 2-143, 2-145, 2-146, 2-147, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2- 155, 2-159, 2-162, 2-163, 2-164, 2-165, 2-166, 2-170, 2-171, 2-172, 2-173, 2-178, 2- 179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-188, 2-189, 2-190, 2-191, 2- 192, 2-193, 2-194, 2-195, 2-197, 2-198, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2- 206, 2-207, 2-208, 2-209, 2-210, 2-211, 2-213, 2-214, 2-215, 2-216, 2-217, 2-218, 2- 219, 2-220, 2-221, 2-222, 2-223, 2-224, 2-225, 2-226, 2-227, 3-6, 3-7, 3-8, 3-9, 3-10, 3-

II, 3-12, 3-13, 3-14, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-25, 3-26, 3- 27, 3-28, 4-1, 5-1,5-2, 5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls. B.11 Tobacco budworm (Heliothis virescens) I

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

After application, microtiter plates were incubated at about 28 ± 1°C and about 80 ± 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed. In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13,

1- 14, 1-15, 2-1,2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-15, 2-17,

2- 18, 2-19, 2-20, 2-21, 2-22, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-34, 2-35, 2-36, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71 , 2-72, 2-73, 2-74, 2-75, 2-77, 2-78, 2-81 , 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91 , 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98,

2- 99, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-110, 2-

III, 2-112, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-122, 2-123, 2- 124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2- 136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143, 2-147, 2-148, 2-149, 2-150, 2- 151, 2-152, 2-153, 2-154, 2-155, 2-156, 2-157, 2-158, 2-160, 2-161, 2-162, 2-163, 2- 164, 2-165, 2-166, 2-167, 2-169, 2-170, 2-171, 2-172, 2-173, 2-174, 2-175, 2-177, 2- 178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-187, 2-188, 2-189, 2- 190, 2-191, 2-192, 2-193, 2-194, 2-195, 2-196, 2-197, 2-198, 2-199, 2-200, 2-201, 2- 202, 2-203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210,2-211, 2-212, 2-213, 2-215, 2- 216, 2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223, 2-224, 2-225, 2-226, 2-227, 3-3,

3- 4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-13, 3-14, 3-15, 3-16, 3-17, 3-18, 3-19, 3- 20, 3-21 , 3-22, 3-23, 3-24, 3-25, 3-26, 3-27, 3-28, 4-1 , 5-1 , 5-2, 5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls. B.12 Boll weevil (Anthonomus grandis)

For evaluating control of boll weevil (Anthonomus grandis) the test unit consisted of 24- well-microtiter plates containing an insect diet and 20-30 A. grandis eggs.

The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 20 μΙ, using a custom built micro atomizer, at two replications.

After application, microtiter plates were incubated at about 23 ± 1 °C and about 50 ± 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed. In this test, the compounds 1 -1 , 1 -2, 1 -3, 1 -4, 1 -5, 1 -7, 1 -8, 1 -9, 1 -10, 1 -1 1 , 1 -12, 1 -13,

1 - 14, 1 -15, 2-1 , 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-1 1 , 2-12, 2-13, 2-15, 2-18,

2- 19, 2-20, 2-21 , 2-22, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31 , 2-32, 2-33, 2-34, 2-35, 2-36, 2-37, 2-38, 2-39, 2-40, 2-41 , 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-51 , 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61 , 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71 , 2-72, 2-73, 2-74, 2-75, 2-76, 2-77, 2-78, 2-79, 2-80, 2-81 , 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91 , 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101 , 2-102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109,

2- 1 10, 2-1 1 1 , 2-1 12, 2-1 13, 2-1 14, 2-1 15, 2-1 16, 2-1 17, 2-1 18, 2-1 19, 2-120, 2-121 , 2- 123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131 , 2-132, 2-133, 2-134, 2- 135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141 , 2-142, 2-143, 2-145, 2-146, 2-147, 2- 148, 2-149, 2-150, 2-151 , 2-152, 2-153, 2-154, 2-155, 2-157, 2-158, 2-160, 2-162, 2- 163, 2-164, 2-165, 2-166, 2-167, 2-168, 2-169, 2-170, 2-171 , 2-172, 2-173, 2-178, 2- 179, 2-180, 2-181 , 2-182, 2-183, 2-184, 2-185, 2-186, 2-187, 2-188, 2-189, 2-190, 2- 191 , 2-192, 2-193, 2-194, 2-195, 2-196, 2-197, 2-198, 2-199, 2-200, 2-201 , 2-202, 2- 203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-21 1 , 2-212, 2-213, 2-214, 2-215, 2- 216, 2-217, 2-218, 2-219, 2-220, 2-221 , 2-222, 2-223, 2-224, 2-225, 2-226, 2-227, 3-3,

3- 4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-1 1 , 3-12, 3-13, 3-14, 3-15, 3-16, 3-17, 3-18, 3-19, 3- 20, 3-21 , 3-22, 3-23, 3-24, 3-25, 3-26, 3-27, 3-28, 4-1 , 5-1 , 5-2, 5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.13 Colorado potato beetle (Leptinotarsa decemlineata)

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). Eggplants were grown 2 plants to a pot and were selected for treatment at the 1 ^st true leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. The treated foliage was then cut and removed from the pot and placed in a 5-inch Petri dish lined with moistened filter paper. Five beetle larvae were introduced into each Petri dish and the dish was covered by a Petri dish lid. Petri dishes were maintained in a growth room at 25°C and 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the dishes. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants.

In this test, the compounds 1 -2, 2-1 , 2-4, 2-5, 2-6, 2-10, 2-1 1 , 2-12, 2-13, 2-19, 2-20, 2- 26, 2-27, 2-28, 2-31 , 2-32, 2-33, 2-35, 2-37, 2-38, 2-40, 2-43, 2-49, 2-50, 2-53, 2-57, 2- 58, 2-59, 2-61 , 2-67, 2-68, 2-71 , 2-72, 2-73, 2-74, 2-82, 2-83, 2-88, 2-89, 2-93, 2-108, 2-1 12, 2-1 16, 2-1 18, 2-1 19, 2-120, 2-124, 2-126, 2-127, 2-128, 2-129, 2-131 , 2-132, 2- 133, 2-135, 2-137, 2-138, 2-141 , 2-143, 2-147, 2-148, 2-149, 2-150, 2-151 , 2-153, 2- 154, 2-155, 2-162, 2-163, 2-165, 2-170, 2-178, 2-179, 2-180, 2-181 , 2-182, 2-185, 2- 186, 2-187, 2-193, 2-197, 2-199, 2-200, 3-4, 3-5, 3-7, 3-8, 3-9, 3-17, and 3-18 at 1 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

B.14 Red spider Mite (Tetranychus kanzawai)

The active compound was dissolved at the desired concentration in a mixture of 1 :1 (v/v) distilled water : acetone. A surfactant (Alkamuls® EL 620) was added at the rate of 0.1 % (v/v).

Potted cowpea beans of 7-10 days of age were cleaned with tap water and sprayed with 5 ml of the test solution using air driven hand atomizer. The treated plants were allowed to air dry and afterwards inculated with 20 or more mites by clipping a cassava leaf section with known mite population. Treated plants were placed inside a holding room at about 25-27°C and about 50-60% relatice humidity.

Mortality was detremined by counting the live mites 72 HAT. Percent mortality was assessed after 72 h. In this test, the compounds 2-1 , 2-2, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-12, 2-13, 2-15, 2-26, 2-27, 2-28, 2-29, 2-30, 2-32, 2-37, 2-40, 2-43, 2-48, 2-51 , 2-54, 2-55, 2-59, 2-60, 2-68, 2-70, 2-71 , 2-72, 2-73, 2-75, 2-77, 2-82, 2-86, 2-97, 2-98, 2-99, 2-100, 2-108, 2- 1 16, 2-1 18, 2-1 19, 2-120, 2-124, 2-126, 2-127, 2-128, 2-129, 2-131 , 2-132, 2-133, 2- 134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141 , 2-142, 2-143, 2-145, 2-146, 2- 147, 2-148, 2-149, 2-151 , 2-153, 2-162, 2-165, 2-166, 2-178, 2-179, 2-180, 2-181 , 2- 182, 2-183, 2-184, 2-185, 2-186, 2-193, 2-195, 2-199, 2-200, 2-201 , 2-202, 2-203, 2- 204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-21 1 , 2-213, 2-214, 2-215, 2-216, 2-217, 2- 218, 2-219, 2-220, 2-221 , 2-222, 2-224, 2-225, 2-226, 3-1 , 3-7, 3-8, 3-10, 3-1 1 , 3-12, 3- 21 , 3-22, 3-23, 3-24, 5-1 , 5-2, and 5-3 at 500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.