N-acylamidine compounds

The present invention relates to N-acylamidine compounds of the formula (I) as defined herein, including their stereoisomers, tautomers and salts, and to compositions comprising such compounds. The invention also relates to the use of the N-acylamidine compounds of the formula (I), their stereoisomers, their tautomers and their salts, for combating invertebrate pests. Furthermore the invention relates also to methods of combating invertebrate pests, which comprises applying such N-acylamidine compounds. Background of Invention

Invertebrate pests, such as insects, acaridae and nematode pests destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and to property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for combating animal pests. In particular, animal pests such as insects and acaridae are difficult to be effectively controlled.

WO 91/04965 describes insecticidall active amidine compounds of the formula A,

alkylidene, F¾ is, inter alia, hydrogen, alkyl, carbamoyl, F¾ is, inter alia, optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl, Z represents N or CH and R ₄ is cyano or nitro.

EP 376 279 describes insecticidally active guanidine derivatives of the formula B

WO 2008/009360 describes compounds of formula A similar to those of WO 91/04965, wherein Ri is aryl, heteroaryl or heterocyclyl, Z is N, R2 is halogenated alkyl, alkenyl or cycloalkyl, R3 is alkyl or cycloalkyl, R ₄ is CN.

WO 97/01537 describes N-methylene thiourea derivatives of the formula C

(C)

wherein Het is a heterocyclic radical, n is 0, 1 or 2, Ri is hydrogen or alkyl and R2 is hydrogen, alkyl, a primary, secondary or tertiary amino group, alkoxy or thioalkyl.

K. Ford et al., J. Agricultural and Food Chemistry describe N'-(aminocarbonyl)-N-[(6- chloro-3-pyridyl)methyl]-N-methyl ethanimidamide as a metabolite of N'-cyano-N-[(6-chloro-3- pyridyl)methyl]-N-methyl ethanimidamide (common name acetamiprid).

The pesticidal activity of the compounds is not satisfactory. It is therefore an object of the present invention to provide compounds having a good pesticidal activity, especially against difficult to control insects and acarid pests.

Summary of Invention

It has been found that these objects are solved by N-acylamidine compounds of the general formula (I) described below, by their stereoisomers, their tautomers and their salts. Therefore, the present invention relates to N-acylamidine compounds of formula (I)

wherein

X is O or S, in particular O;

Het is a 5- or 6-membered carbon-bound or nitrogen-bound, saturated, partly unsaturated or aromatic heterocyclic radical comprising 2, 3, 4 or 5 carbon atoms and 1 , 2 or 3 heteroatoms as ring members, which are independently selected from sulfur, oxygen or nitrogen, wherein the sulfur and nitrogen ring members can independently be partly or fully oxidized, and wherein each ring is optionally substituted by k identical or different substituents R ⁶ , wherein k is an integer selected from 0, 1 , 2, 3 or 4; are independently from each other selected from the group consisting of hydrogen, halogen, CN, SCN, nitro, Ci-C6-alkyl, C3-C6-cycloalkyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R ⁷ ,

Si(R ¹¹ ) ₂ R ¹² , OR ⁸ , OS0 ₂ R ^8a , S(0) _n R ^8a , S(0) _n NR ^9a R ^9b , NR ^9a R ^9b , C(=0)NR ^9a R ^9b ,

C(=S)NR ^a R ^b , C(=0)OR ⁸ , C(=0)R ^7a , C(=S)R ^7a , phenyl, benzyl, where the phenyl ring in the last two radicals is unsubstituted or optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or

R ¹ and R ² form, together with the carbon atom, which they attached to, a 3-,

4-, 5- or 6-membered saturated or partly unsaturated carbocyclic or heterocyclic ring, wherein each of the carbon atoms of said cycle are unsubstituted or may carry any combination of 1 or 2 identical or different radicals R ⁷ , or

R and R ² may together be =0, =CR ¹³ R ¹⁴ , =S, =NR ¹⁷ , =NOR ¹⁶ or =NNR ^9a R ⁹ ; is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R ⁷ ,

C3-C6-cycloalkyl, which is unsubstituted or may carry any combination of 1 , 2, 3, 4 or 5 radicals R ¹⁰ ,

NR ^9a R ⁹ , C(=0)NR ^9a R ⁹ , C(=S)NR ^9a R ⁹ , OR ⁸ , S(0) _n R ^8a , C(=0)OR ⁸ , C(=0)R ^7a , C(=S)R ^7a ,

Cyc ¹ -Q ¹ , where Cyc ¹ is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ,

Q ¹ is Ci-C4-alkanediyl or C2-C4-alkenediyl; is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R ⁷ ,

C3-C6-cycloalkyl, which is unsubstituted or may carry any combination of 1 , 2, 3, 4 or 5 radicals R ¹⁰ ,

OR ⁸ , S(0) _n R ^8a , C(=N-0-R ^16a )R ¹⁵ , Cyc ² -Q ² , where

Cyc ² is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ,

Q ² is Ci-C4-alkanediyl or C2-C4-alkenediyl; is selected from radicals R ^4a , R ^4b , R ^4c and R ^4d , where

R ^4a is selected from the group consisting of Ci-Cio-alkyl, C2-Cio-alkenyl, C2-C10- alkynyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R ^5a ,

C3-Cio-cycloalkyl, which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ^10a ,

3-, 4-, 5- or 6-membered, saturated heterocyclyl, which carries 1 or 2 oxygen or nitrogen atoms as ring members and where heterocyclyl is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ^10a , and

Cyc ³ -Q ³ , where

Cyc ³ is phenyl or a 5- or 6-membered aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ,

Q ³ is a single bond, Ci-C4-alkanediyl or C2-C4-alkenediyl;

R ^4b is 0-R ^5b ;

R ^4c is S-R ^5c ;

R ^4d is NR ^5d R ^5e ; independently of its occurrence, is selected from the group consisting of cyano, azido, nitro, -SCN, SF ₅ , Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6- alkenyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -alkynyl, C ₂ -C ₆ haloalkynyl, Si(R ¹¹ ) ₂ R ¹² , OR ⁸ , OS0 ₂ R ^8a , 0-N=CR ¹³ R ¹⁴ , S(0) _n R ^8a , S(0) _n NR ^7a R ^7b , NR ^17a R ^17b ,

C(=0)NR ^7a R ⁷ , C(=S)NR ^7a R ⁷ , C(=0)OR ⁸ , C(=0)R ¹⁵ , C(=S)R ¹⁵ ,

C(=NR ⁷ )R ¹⁵ , NR ^7a -C(=0)R ^7a , NR ^7a -C(=S)R ^7a , NR ^7a -C(=0)OR ⁸ ,

NR ^7a -C(=0)NR ^7a R ⁷ ,

phenyl, phenoxy, phenyl-Ci-C4-alkyloxy, where the phenyl ring in the last three groups is optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and

a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,

or two R ^5a present on one carbon atom may together form =0, =CR ¹³ R ¹⁴ , =S, =NR ¹⁷ , =NOR ¹⁶ , =NNR ^9a R ^9b ,

or two R ^5a may form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partly unsaturated carbocyclic or heterocyclic ring together with the carbon atoms to which the two R ^5a are bonded, where the heterocyclic ring comprises 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ ;

R ^5c independently of each other are selected from the group consisting of Ci-Cio-alkyl, C ₂ -Cio-alkenyl, C ₂ -Cio-alkynyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R ^5a ,

C3-Cio-Cycloalkyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , C(=0)NR ^9a R ^9b , C(=S)NR ^9a R ^9b , C(=0)OR ⁸ , C(=0)R ^7a , C(=S)R ^7a ,

phenyl and phenyl-Ci-C4-alkyl, where the phenyl ring in the last two mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ;

R ^5d , R ^5e independently of each other are selected from the group consisting of hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R ^5a , C3-Cio-Cycloalkyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ,

OR ⁸ , NR ^9a R ^9b , C(=0)NR ^9a R ^9b , C(=S)NR ^9a R ⁹ , C(=0)OR ⁸ , C(=0)R ^7a , C(=S)R ^7a , phenyl and phenyl-Ci-C4-alkyl, where the phenyl ring in the last two mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , or

R ^5d and R ^5e , if present, together may also form a bivalent radical, selected from the group consisting of C2-C6-alkanediyl and C2-C6-alkenediyl, wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R ^7c , provided that at least one of the radicals R ^5d and R ^5e is different from hydrogen; where, independently of their occurrence, n is 0, 1 or 2;

R ⁶ is 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, and wherein the carbon atoms of the last 4 aliphatic and cycloaliphatic radicals may be partially or completely halogenated and/or further substituted independently from one another with 1 , 2 or 3 radicals R ⁷ ,

OR ⁸ , NR ^17a R ^17b , S(0) _n R ^8a , S(0) _n NR ^7a R ⁷ , C(=0)R ^7a , C(=0)NR ^7a R ⁷ , C(=0)OR ⁸ , C(=S)R ^7a , C(=S)NR ^7a R ⁷ , C(=S)OR ⁸ , C(=S)SR ^8a , C(=NR ⁷ )R ^7a , C(=NR ⁷ )NR ^7a R ⁷ , Si(R ¹¹ ) ₂ R ¹² ;

phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents

R ¹⁰ ,

and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,

or two of R ⁶ present on one ring carbon may together form =0, =CR ¹³ R ¹⁴ , =S, =NR ¹⁷ , =NOR ¹⁶ , =NNR ^9a R ^9b ,

or two R ⁶ together form a linear C2-C7-alkylene chain, thus forming, together with the ring atom(s) to which they are bound, a 3-, 4-, 5-, 6-, 7- or 8-membered ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O, S and NR ^17c and/or 1 or 2 of the CH2 groups of the alkylene chain may be replaced by a group C=0, C=S and/or C=NR ¹⁷ ; and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, 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, phenyl which may be substituted with 1 , 2, 3, 4 or 5 radicals R ¹⁰ , 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 with 1 , 2, 3, 4 or 5 radicals R ¹⁰ ; independently of its occurrence, is selected from the group consisting of cyano, azido, nitro, -SCN, SF ₅ , d-C ₆ -alkyl, Ci-C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ - halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, Si(R ¹¹ ) ₂ R ¹² , OR ⁸ , OS0 ₂ R ^8a , S(0) _n R ^8a , S(0) _n NR ^7a R ^7b , NR ^17a R ^17b , C(=0)NR ^7a R ^7b , C(=S)NR ^7a R ⁷ , C(=0)OR ⁸ , C(=0)R ¹⁵ , C(=S)R ¹⁵ , C(=NR ⁷ )R ¹⁵ , NR ^7a -C(=0)R ^7a , NR ^7a -C(=S)R ^7a , NR ^7a -C(=0)OR ⁸ , NR ^7a -C(=0)NR ^7a R ⁷ ,

phenyl, phenoxy, phenyl-Ci-C4-alkyl, where the phenyl ring in the last three groups is optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,

or two R ⁷ present on one carbon atom may together form =0, =CR ¹³ R ¹⁴ , =S, =NR ¹⁷ , =NOR ^16a , =NNR ^9a R ^9b ,

or two R ⁷ may form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partly unsaturated carbocyclic or heterocyclic ring together with the carbon atoms to which the two R ⁷ are bonded, where the heterocyclic ring comprises 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ ; independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C6- cycloalkyl-Ci-C4-alkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C2-C6 haloalkynyl,

phenyl or benzyl, where the phenyl ring in the last two radicals is optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and

a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; independently of its occurrence, is selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs- halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C2-C6 haloalkynyl,

phenyl and benzyl, wherein the phenyl ring of the two last-mentioned radicals is optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,

or two of R ^7c present on one carbon may together form =0, =CR ¹³ R ¹⁴ , =S, =N R ¹⁷ , =NOR ^16a , =N N R ^9a R ^9b ; independently of its occurrence, is selected from the group consisting of hydrogen, d-Ce-alkyl, Ci-C ₆ -haloalkyl, Cs-Cs-cycloalkyl, C ₃ -Ce-cycloalkyl-Ci-C4-alkyl, Cs-Cs- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, C(=0)R ¹⁵ , C(=0)N R ^7a R ^7b , C(=S)N R ^7a R ^7b , C(=0)OR ^16a ,

phenyl, phenyl-Ci-C-4-alkyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and

a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; independently of its occurrence, is selected from the group consisting of hydrogen, d-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, phenyl, phenyl-Ci-C- ₄ -alkyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and

a 5- or 6-membered aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ ;

R ^9b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3- C8-cycloalkyl-Ci-C ₄ -alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2- C6-haloalkynyl,

S(0) _n R ^16a , -S(0) _n NR ^7a R ^7b , C(=0)R ¹⁵ , C(=0)OR ^16a , C(=0)NR ^7a R ^7b ,

C(=S)R ¹⁵ , C(=S)SR ^16a , C(=S)NR ^7a R ^7b , C(=NR ⁷ )R ¹⁵ ;

phenyl, benzyl, 1 -phenethyl or 2-phenethyl, where the phenyl ring in the last four mentioned radicals is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ; and

a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic C- bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,

or,

and R ^9b are together a C2-C7-alkylene chain and form a 3-, 4-, 5-, 6-, 7- or 8- membered saturated, partly unsaturated or aromatic ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur or nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C2-C6-haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,

or

and R ^9b together may form =CR ¹³ R ¹⁴ , =NR ¹⁷ or =NOR ^16a moiety; independently of its occurrence, is selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF ₅ , Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the carbon atoms of the three aforementioned aliphatic radicals may optionally be substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN, SF ₅ , OH, CN, NO2, Cs-Ce-cycloalkyl, Ci-Ce- haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci- C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,

Cs-Cs-cycloalkyI, which is unsubstituted or carries 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN, SF ₅ , OH, CN, NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci- C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyl- oxy and (Ci-C6-alkoxy)carbonyl,

Si(R ¹¹ ) ₂ R ¹² , OH, SH, OR ^16a , OS(0) _n R ^16a , -S(0) _n R ^16a , S(0) _n NR ^7a R ^7b , NR ^17a R ^17b , C(=0)R ¹⁵ , C(=S)R ¹⁵ , C(=0)OR ^16a , -C(=NR ⁷ )R ¹⁵ , C(=0)NR ^7a R ^7b , C(=S)NR ^7a R ⁷ , phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from halogen, OH, CN, N0 ₂ , SCN, SF ₅ , OH, Ci-C ₆ -alkyl, C ₃ -C ₆ -cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)- amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 substituents selected independently from one another from halogen, OH, CN, NO2, SCN, SF ₅ , OH, C1-C6- alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;

or

two R ¹⁰ present together on one carbon ring atom of a saturated or partly unsaturated heterocyclic radical may form =0, =CR ¹³ R ¹⁴ , =S, =NR ¹⁷ , =NOR ^16a , =NNR ^17a R ^17b ;

or,

two R ¹⁰ on adjacent carbon ring atoms may also be a bivalent radical selected from CH2CH2CH2CH2, CH=CH-CH=CH, N=CH-CH=CH, CH=N-CH=CH, N=CH-N=CH, OCH2CH2CH2, OCH=CHCH ₂ , CH2OCH2CH2, OCH2CH2O, OCH2OCH2, CH2CH2CH2, CH=CHCH ₂ , CH2CH2O, CH=CHO, CH ₂ OCH ₂ , CH ₂ C(=0)0, C(=0)OCH ₂ , 0(CH ₂ )0, SCH2CH2CH2, SCH=CHCH ₂ , CH2SCH2CH2, SCH2CH2S, SCH2SCH2, CH2CH2S,

CH=CHS, CH2SCH2, CH ₂ C(=S)S, C(=S)SCH ₂ , S(CH ₂ )S, CH ₂ CH ₂ NR ¹⁷ , CH ₂ CH=N, CH=CH-NR ¹⁷ , OCH=N, SCH=N and form together with the carbon atoms to which the two R ¹⁰ are bonded to a 5-membered or 6-membered partly saturated or unsaturated, aromatic carbocyclic or heterocyclic ring, wherein the ring may optionally be substituted with one or two substituents selected from =0, OH, CH3,

OCH3, halogen, cyano, halomethyl and halomethoxy;

R ^10a independently of its occurrence, is selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF ₅ , Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the carbon atoms of the three aforementioned aliphatic radicals may optionally be substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN, SF ₅ , OH, CN, NO2, Cs-Ce-cycloalkyl, Ci-Ce- haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci- C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,

Cs-Cs-cycloalkyI, which is unsubstituted or carries 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN , SF ₅ , OH, CN, NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-

C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyl- oxy and (Ci-C6-alkoxy)carbonyl,

Si(R ¹¹ ) ₂ R ¹² , OR ^16a , OS(0) _n R ^16a , -S(0) _n R ^8a , S(0) _n NR ^7a R ^7b , NR ^17a R ^17b , C(=0)R ¹⁵ , C(=S)R ¹⁵ , C(=0)OR ^16a , -C(=NR ⁷ )R ¹⁵ , C(=0)NR ^7a R ^7b , C(=S)NR ^7a R ⁷ , phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from halogen, OH, CN, N0 ₂ , SCN, SF ₅ , OH, Ci-C ₆ -alkyl, C ₃ -C ₆ -cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)- amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 substituents selected independently from one another from halogen, OH, CN, NO2, SCN, SF ₅ , OH, C1-C6- alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;

or

two R ^10a present together on one carbon ring atom of a saturated or partly unsaturated heterocyclic radical may form =0, =CR ¹³ R ¹⁴ , =S, =NR ¹⁷ , =NOR ^16a , =NNR ^17a R ^17b ;

or,

two R ^10a on adjacent carbon ring atoms may also be a bivalent radical selected from CH2CH2CH2CH2, CH=CH-CH=CH, N=CH-CH=CH, CH=N-CH=CH, N=CH-N=CH, OCH2CH2CH2, OCH=CHCH ₂ , CH2OCH2CH2, OCH2CH2O, OCH2OCH2, CH2CH2CH2, CH=CHCH ₂ , CH2CH2O, CH=CHO, CH ₂ OCH ₂ , CH ₂ C(=0)0, C(=0)OCH ₂ , 0(CH ₂ )0, SCH2CH2CH2, SCH=CHCH2, CH2SCH2CH2, SCH2CH2S, SCH2SCH2, CH2CH2S, CH=CHS, CH2SCH2, CH ₂ C(=S)S, C(=S)SCH ₂ , S(CH ₂ )S, CH ₂ CH ₂ NR ¹⁷ , CH ₂ CH=N, CH=CH-NR ¹⁷ , OCH=N , SCH=N and form together with the carbon atoms to which the two R ^10a are bonded to a 5-membered or 6-membered partly saturated or unsaturated, aromatic carbocyclic or heterocyclic ring, wherein the ring may optionally be substituted with one or two substituents selected from =0, OH, CH3, OCH3, halogen, cyano, halomethyl and halomethoxy;

R ¹² independently of their occurrence, are selected from the group consisting of d-Ce-alkyl, Ci-C ₆ -haloalkyl, Ci-C ₆ -alkoxy, Ci-C ₆ -alkoxy-Ci-C ₄ -alkyl, C ₂ -C ₆ - alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-Ci-C ₄ -alkyl, C3-C8-halocycloalkyl-Ci-C ₄ - alkyl, Ci-C6-haloalkoxy-Ci-C ₄ -alkyl, phenyl and benzyl, where the phenyl ring in last two radicals are unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N0 ₂ , SCN, SF ₅ , OH, Ci-C ₆ -alkyl, C ₃ -C ₆ -cycloalkyl, Ci- C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci- C6-alkoxy)carbonyl;

R ¹³ , R ¹⁴ independently of their occurrence, are selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy-Ci-C4- alkyl, phenyl and benzyl; R ¹⁵ independently of its occurrence, is selected from the group consisting of hydrogen,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from C1-C4 alkoxy;

phenyl, benzyl and pyridyl, wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2, SCN, SF ₅ , OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci- C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;

R ¹⁶ independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals R ⁷ , and

Cyc ⁴ -Q ⁴ , where

Cyc ⁴ is phenyl or a 5- or 6-membered aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ,

Q ⁴ is Ci-C4-alkanediyl or C2-C4-alkenediyl;

R ^16a independently of its occurrence, is selected from the group consisting of

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the three aforementioned aliphatic radicals may optionally be substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN, SF ₅ , OH, CN, N0 ₂ , Cs-Ce-cycloalkyl, d-C ₆ -haloalkyl, Ci-C ₆ -alkoxy, Ci-C ₆ haloalkoxy, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (C1-C6- alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, Cs-Cs-cycloalkyI, which is unsubstituted or carries 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN , SF ₅ , OH, CN, NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (C1-C6- alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,

phenyl, benzyl, pyridyl and pyridylmethyl, wherein the last four radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2, SCN, SF ₅ , OH, Ci-Ce-alkyl, C ₃ -C ₆ -cycloalkyl, Ci-C ₆ -haloalkyl, Ci-C ₆ -alkoxy, Ci-C ₆ haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl; independently of its occurrence, is selected from the group consisting of hydrogen, trimethylsilyl, triethylsilyl, fe/7-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyI, C3-C8-cycloalkyl-Ci-C4- alkyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Cs-Cs-cycloalkoxy, C3-C8- cycloalkyl-Ci-C4-alkoxy, Ci-C6-alkylthio, wherein the 1 1 last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy, phenyl, benzyl, pyridyl, phenoxy, benzyloxy and pyridyloxy, wherein the six last mentioned radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N0 ₂ , SCN, SF ₅ , OH, Ci-Ce-alkyl, C ₃ -C ₆ -cycloalkyl, Ci-C ₆ - haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci- C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;

, R ^17b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, fe/7-butyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyI, wherein the four last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy, phenyl, benzyl, pyridyl and phenoxy, wherein the four last mentioned radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N0 ₂ , Ci-Ce-alkyl, Ci-C ₆ -haloalkyl, Ci-C ₆ -alkoxy, Ci-C ₆ haloalkoxy, Ci- C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (C1-C6- alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,

or,

R ^17a and R ^17b may together be a C2-C6-alkylene chain forming a 3- to 7- membered saturated, partly saturated or unsaturated ring together with the nitrogen atom R ^17a and R ^17b are bonded to, wherein the alkylene chain may contain 1 or 2 heteroatoms selected, independently of each other, from oxygen, sulfur or nitrogen, and may optionally be substituted with halogen, Ci- C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;

R ^17c independently of its occurrence, is selected from the group consisting of hydrogen, CN, d-Ce-alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₃ -Ce-cycloalkyl, C ₃ -C ₈ -cycloalkyl-Ci- C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from C1-C4 alkoxy, phenyl, benzyl and pyridyl, wherein the last three radicals may be unsubstituted, partially or fully halogenated and/or to carry 1 , 2 or 3 substituents selected from Ci- C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci- C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (C1-C6- alkoxy)carbonyl; the stereoisomers, tautomers and the salts thereof.

In a special embodiment, the present invention relates to N-acylamidine compounds of formula (I):

(I)

wherein

X is O or S, in particular O, is a 5- or 6-membered carbon-bound or nitrogen-bound, saturated, partly unsaturated or aromatic heterocyclic radical comprising 2, 3, 4 or 5 carbon atoms and 1 , 2 or 3 heteroatoms as ring members, which are independently selected from sulfur, oxygen or nitrogen, wherein the sulfur and nitrogen ring members can independently be partly or fully oxidized, and wherein each ring is optionally substituted by k identical or different substituents R ⁶ , wherein k is an integer selected from 0, 1 , 2, 3 or 4; are independently from each other selected from the group consisting of hydrogen, halogen, CN, SCN, nitro, Ci-C6-alkyl, C3-C6-cycloalkyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R ⁷ ,

Si(R ¹¹ ) ₂ R ¹² , OR ⁸ , OS0 ₂ R ^8a , S(0) _n R ^8a , S(0) _n NR ^9a R ^9b , NR ^9a R ^9b , C(=0)NR ^9a R ^9b , C(=S)NR ^a R ^b , C(=0)OR ⁸ , C(=0)R ^7a , C(=S)R ^7a , phenyl, benzyl, where the phenyl ring in the last two radicals is unsubstituted or optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents

R ¹⁰ , and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or

R ¹ and R ² form, together with the carbon atom, which they attached to, a 3-, 4-, 5- or 6-membered saturated or partly unsaturated carbocyclic or heterocyclic ring, wherein each of the carbon atoms of said cycle are unsubstituted or may carry any combination of 1 or 2 identical or different radicals R ⁷ . or

R and R ² may together be =0, =CR ¹³ R ¹⁴ , =S, =NR ¹⁷ , =NOR ¹⁶ or =NNR ^9a R ⁹ ; is selected from the group consisting of hydrogen, CN , Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any

combination of 1 , 2 or 3 radicals R ⁷ ,

C3-C6-cycloalkyl, which is unsubstituted or carries any combination of 1 , 2, 3, 4 or 5 radicals R ¹⁰ ,

C(=0)NR ^9a R ^9b , C(=S)NR ^9a R ^9b , OR ⁸ , S(0) _n R ^8a , C(=0)OR ⁸ , C(=0)R ^7a

Cyc ¹ -Q ¹ , where

Cyc ¹ is phenyl or a 3-, 4-, 5-, 6- or 7-membered , saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ,

Q ¹ is Ci-C4-alkandiyl or C2-C4-alkendiyl; is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any

combination of 1 , 2 or 3 radicals R ⁷ ,

C3-C6-cycloalkyl, which is unsubstituted or carries any combination of 1 , 2, 3, 4 or 5 radicals R ¹⁰ ,

OR ⁸ , S(0) _n R ^8a , C(=N-0-R ^16a )R ¹⁵ ,

Cyc ² -Q ² , where

Cyc ² is phenyl or a 3-, 4-, 5-, 6- or 7-membered , saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ,

Q ² is Ci-C4-alkandiyl or C2-C4-alkendiyl; is selected from radicals R ^4a , R ^4b , R ^4c and R ^4d , where

R ^4a is selected from the group consisting of Ci-Cio-alkyl, C2-Cio-alkenyl, C2-C10- alkynyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R ^5a ,

C3-Cio-cycloalkyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and

Cyc ³ -Q ³ , where

Cyc ³ is phenyl or a 5- or 6-membered aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ,

Q ³ is Ci-C4-alkandiyl or C2-C4-alkendiyl; is 0-R ^5b , is S-R ^5c , is NR ^5d R ^5e , independently of its occurrence, is selected from the group consisting of cyano, azido, nitro, -SCN, SF ₅ , Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6- alkenyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -alkynyl, C ₂ -C ₆ haloalkynyl, Si(R ¹¹ ) ₂ R ¹² , OR ⁸ , OS0 ₂ R ^8a , 0-N=CR ¹³ R ¹⁴ , S(0) _n R ^8a , S(0) _n NR ^7a R ^7b , NR ^17a R ^17b ,

C(=0)NR ^7a R ^7b , C(=S)NR ^7a R ⁷ , C(=0)OR ⁸ , C(=0)R ¹⁵ , C(=S)R ¹⁵ ,

C(=NR ⁷ )R ¹⁵ , NR ^7a -C(=0)R ^7a , NR ^7a -C(=S)R ^7a , NR ^7a -C(=0)OR ⁸ ,

NR ^7a -C(=0)NR ^7a R ⁷ ,

phenyl, phenoxy, phenyl-Ci-C4-alkyloxy, where the phenyl ring in the last three groups is optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and

and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,

or two R ^5a present on one carbon atom may together form =0, =CR ¹³ R ¹⁴ , =S, =NR ¹⁷ , =NOR ¹⁶ , =NNR ^9a R ^9b ,

or two R ^5a may form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partly unsaturated carbocyclic or heterocyclic ring together with the carbon atoms to which the two R ^5a are bonded, where the heterocyclic ring comprises 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ ;

R ^5b , R ^5c independently of each other are selected from the group consisting of Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R ^5a ,

C3-Cio-Cycloalkyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ,

C(=0)NR ^9a R ^9b , C(=S)NR ^9a R ^9b , C(=0)OR ⁸ , C(=0)R ^7a , C(=S)R ^7a ,

phenyl and phenyl-Ci-C4-alkyl, where the phenyl ring in the last two mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ; R ^5d , R ^5e independently of each other are selected from the group consisting of hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R ^5a , C3-Cio-Cycloalkyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ,

OR ⁸ , NR ^9a R ^9b , C(=0)NR ^9a R ⁹ , C(=S)NR ^9a R ⁹ , C(=0)OR ⁸ , C(=0)R ^7a , C(=S)R ^7a , phenyl and phenyl-Ci-C4-alkyl, where the phenyl ring in the last two mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , or

R ^5d and R ^5e , if present, together may also form a bivalent radical, selected from the group consisting of C2-C6-alkandiyl and C2-C6-alkendiyl, wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R ^7c ,

provided that at least one of the radicals R ^5d and R ^5e is different from hydrogen; where, independently of their occurrence, n is 0, 1 or 2; R ⁶ is 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, and wherein the carbon atoms of the last 4 aliphatic and cycloaliphatic radicals may be partially or completely halogenated and/or further substituted independently from one another with 1 , 2 or 3 radicals R ⁷ , OR ⁸ , NR ^17a R ^17b , S(0) _n R ^8a , S(0) _n NR ^7a R ^7b , C(=0)R ^7a , C(=0)NR ^7a R ^7b , C(=0)OR ⁸ , C(=S)R ^7a , C(=S)NR ^7a R ^7b , C(=S)OR ⁸ , C(=S)SR ^8a , C(=NR ⁷ )R ^7a , C(=NR ⁷ )NR ^7a R ⁷ , Si(R ¹¹ ) ₂ R ¹² ;

phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents

R ¹⁰ ,

and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,

or two of R ⁶ present on one ring carbon may together form =0, =CR ¹³ R ¹⁴ , =S, =NR ¹⁷ , =NOR ¹⁶ , =NNR ^9a R ^9b ,

or two R ⁶ together form a linear C2-C7 alkylene chain, thus forming, together with the ring atom(s) to which they are bound, a 3-, 4-, 5-, 6-, 7- or 8-membered ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O, S and NR ^17c and/or 1 or 2 of the CH2 groups of the alkylene chain may be replaced by a group C=0, C=S and/or C=NR ¹⁷ ; and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, 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, phenyl which may be substituted with 1 , 2, 3, 4 or 5 radicals R ¹⁰ , 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 with 1 , 2, 3, 4 or 5 radicals R ¹⁰ ; independently of its occurrence, is selected from the group consisting of cyano, azido, nitro, -SCN, SF ₅ , d-C ₆ -alkyl, Ci-C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ - halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, Si(R ¹¹ ) ₂ R ¹² , OR ⁸ , OS0 ₂ R ^8a , S(0) _n R ^8a , S(0) _n NR ^7a R ⁷ , NR ^17a R ^17b , C(=0)NR ^7a R ⁷ , C(=S)NR ^7a R ⁷ , C(=0)OR ⁸ , C(=0)R ¹⁵ , C(=S)R ¹⁵ , C(=NR ⁷ )R ¹⁵ , NR ^7a -C(=0)R ^7a , NR ^7a -C(=S)R ^7a , NR ^7a -C(=0)OR ⁸ , NR ^7a -C(=0)NR ^7a R ⁷ ,

phenyl, phenoxy, phenyl-Ci-C4-alkyl, where the phenyl ring in the last three groups is optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,

or two R ⁷ present on one carbon atom may together form =0, =CR ¹³ R ¹⁴ , =S, =N R ¹⁷ , =NOR ^16a , =N N R ^9a R ^9b ,

or two R ⁷ may form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partly unsaturated carbocyclic or heterocyclic ring together with the carbon atoms to which the two R ⁷ are bonded, where the heterocyclic ring comprises 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ ; independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and

and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; independently of its occurrence, is selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and

and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,

or two of R ^7b present on one carbon may together form =0, =CR ¹³ R ¹⁴ , =S, =N R ¹⁷ , =NOR ^16a , =N N R ^9a R ^9b ; independently of its occurrence, is selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ - halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and

and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,

or two of R ^7c present on one carbon may together form =0, =CR ¹³ R ¹⁴ , =S, =NR ¹⁷ , =NOR ^16a , =NNR ^9a R ^9b ; independently of its occurrence, is selected from the group consisting of hydrogen, d-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, C(=0)R ¹⁵ , C(=0)NR ^7a R ^7b , C(=S)NR ^7a R ^7b , C(=0)OR ^16a ,

phenyl, phenyl-Ci-C- ₄ -alkyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and

and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, independently of its occurrence, is selected from the group consisting of hydrogen, d-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, phenyl, phenyl-Ci-C- ₄ -alkyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and

and a 5- or 6-membered aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ ; are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -halocycloalkyl, C ₃ - C8-cycloalkyl-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2- C6 haloalkynyl,

S(0) _n R ^16a , -S(0) _n NR ^7a R ^7b , C(=0)R ¹⁵ , C(=0)OR ^16a , C(=0)NR ^7a R ^7b , C(=S)R ¹⁵ , C(=S)SR ^16a , C(=S)NR ^7a R ^7b , C(=NR ⁷ )R ¹⁵ ;

phenyl, benzyl, 1 -phenethyl or 2-phenethyl, where the phenyl ring in the last four mentioned radicals is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ; and

and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,

or,

R ^9a and R ^9b are together a C2-C7 alkylene chain and form a 3-, 4-, 5-, 6-, 7- or 8- membered saturated, partly unsaturated or aromaticring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur or nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic C-bound heterocyclic ring comprising

1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,

or

R ^9a and R ^9b together may form =CR ¹³ R ¹⁴ , =NR ¹⁷ or =NOR ^16a moiety; independently of its occurrence, is selected from the group consisting of halogen, cyano, azido, nitro, SCN , SF ₅ ,

Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the carbon atoms of the three aforementioned aliphatic radicals may optionally be substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN , SF ₅ , OH , CN , N0 ₂ , Cs-Ce-cycloalkyl, Ci-C ₆ -haloalkyl, Ci-C ₆ -alkoxy, Ci-C ₆ haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,

Cs-Cs-cycloalkyI, which is unsubstituted or carries 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN , SF ₅ , OH , CN , NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy,

Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci- C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyl- oxy and (Ci-C6-alkoxy)carbonyl,

Si(R ^{1 1} ) ₂ R ¹² , OR ^16a , OS(0) _n R ^16a , -S(0) _n R ^16a , S(0) _n N R ^7a R ^7b , N R ^17a R ^17b , C(=0)R ¹⁵ , C(=S)R ¹⁵ , C(=0)OR ^16a , -C(=N R ⁷ )R ¹⁵ , C(=0)N R ^7a R ^7b , C(=S)N R ^7a R ^7b ,

phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from halogen, OH , CN , N0 ₂ , SCN , SF ₅ , OH , Ci-C ₆ -alkyl, C ₃ -C ₆ -cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)- amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, and

and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 substituents selected independently from one another from halogen, OH , CN , NO2, SCN , SF ₅ , OH , d-Ce-alkyl, C ₃ -C ₆ -cycloalkyl, Ci-Ce-haloalkyI, Ci-Ce-alkoxy, Ci-C ₆ haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;

or

two R ¹⁰ present together on one carbon ring atom of a saturated or partly unsaturated heterocyclic radical may form =0, =CR ¹³ R ¹⁴ , =S, =N R ¹⁷ , =NOR ^16a , =N N R ^17a R ^17b ;

or,

two R ¹⁰ on adjacent carbon ring atoms may also be a bivalent radical selected from CH2CH2CH2CH2, CH=CH-CH=CH , N=CH-CH=CH , CH=N-CH=CH , N=CH-N=CH , OCH2CH2CH2, OCH =CHCH ₂ , CH2OCH2CH2, OCH2CH2O, OCH2OCH2, CH2CH2CH2, CH=CHCH ₂ , CH2CH2O, CH=CHO, CH ₂ OCH ₂ , CH ₂ C(=0)0, C(=0)OCH ₂ , 0(CH ₂ )0,

SCH2CH2CH2, SCH =CHCH2, CH2SCH2CH2, SCH2CH2S, SCH2SCH2, CH2CH2S, CH=CHS, CH2SCH2, CH ₂ C(=S)S, C(=S)SCH ₂ , S(CH ₂ )S, CH ₂ CH ₂ N R ¹⁷ , CH ₂ CH=N , CH=CH-N R ¹⁷ , OCH =N , SCH=N and form together with the carbon atoms to which the two R ¹⁰ are bonded to a 5-membered or 6-membered partly saturated or unsaturated, aromatic carbocyclic or heterocyclic ring, wherein the ring may optionally be substituted with one or two substituents selected from =0, OH, CH3, OCH3, halogen, cyano, halomethyl and halomethoxy;

R ¹² independently of their occurrence, are selected from the group consisting of d-Ce-alkyl, Ci-C ₆ -haloalkyl, Ci-C ₆ -alkoxy, Ci-C ₆ -alkoxy-Ci-C ₄ -alkyl, C ₂ -C ₆ - alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-Ci-C ₄ -alkyl, C3-Cs-halocycloalkyl-Ci-C ₄ - alkyl, Ci-C6-haloalkoxy-Ci-C ₄ -alkyl, phenyl and benzyl, where the phenyl ring in last two radicals are unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N0 ₂ , SCN, SF ₅ , OH, Ci-C ₆ -alkyl, C ₃ -C ₆ -cycloalkyl, Ci- C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkyl- thio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (C1-C6- alkoxy)carbonyl;

R ¹⁴ independently of their occurrence, are selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C ₄ -alkoxy-Ci-C ₄ - alkyl, phenyl and benzyl; independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C ₄ - alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C ₄ alkoxy;

phenyl, benzyl and pyridyl, wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2, SCN, SF ₅ , OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl; independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C ₄ - alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals R ⁷ , and Cyc ⁴ -Q ⁴ , where

Cyc ⁴ is phenyl or a 5- or 6-membered aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , Q ⁴ is Ci-C4-alkandiyl or C2-C4-alkendiyl;

R ^16a independently of its occurrence, is selected from the group consisting of

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the three aforementioned aliphatic radicals may optionally be substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN, SF ₅ , OH, CN, N0 ₂ , Cs-Ce-cycloalkyl, Ci-C ₆ -haloalkyl, Ci-C ₆ -alkoxy, Ci-C ₆ haloalkoxy, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (C1-C6- alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,

Cs-Cs-cycloalkyI, which is unsubstituted or carries 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN , SF ₅ , OH, CN, NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)- carbonyloxy and (Ci-C6-alkoxy)carbonyl,

phenyl, benzyl, pyridyl and pyridylmethyl, wherein the last four radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2, SCN, SF ₅ , OH, d-Ce-alkyl, C ₃ -C ₆ -cycloalkyl, d-Ce-haloalkyl, Ci-C ₆ -alkoxy, Ci-C ₆ haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-halo- alkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci- C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;

R ¹⁷ independently of its occurrence, is selected from the group consisting of hydrogen, trimethylsilyl, triethylsilyl, fe/ibutyldimethylsilyl,

Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyI, C3-C8-cycloalkyl-Ci-C4- alkyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Cs-Cs-cycloalkoxy, C3-C8- cycloalkyl-Ci-C4-alkoxy, Ci-C6-alkylthio, wherein the 1 1 last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy, phenyl, benzyl, pyridyl, phenoxy, benzyloxy and pyridyloxy, wherein the six last mentioned radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N0 ₂ , SCN, SF ₅ , OH, Ci-C ₆ -alkyl, C ₃ -C ₆ -cycloalkyl, Ci-C ₆ - haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci- C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;

R ^17a , R ^17b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, fe/ibutyldimethylsilyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy, phenyl, benzyl, pyridyl and phenoxy, wherein the four last mentioned radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH , CN , N0 ₂ , d-Ce-alkyl, Ci-C ₆ -haloalkyl, Ci-C ₆ -alkoxy, Ci-C ₆ haloalkoxy, Ci- C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (C1-C6- alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,

or,

R ^17a and R ^17b may together be a C2-C6 alkylene chain forming a 3- to 7- membered saturated, partly saturated or unsaturated ring together with the nitrogen atom R ^17a and R ^17b are bonded to, wherein the alkylene chain may contain 1 or 2 heteroatoms selected, independently of each other, from oxygen, sulfur or nitrogen, and may optionally be substituted with halogen, Ci- C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;

R ^17c independently of its occurrence, is selected from the group consisting of hydrogen, CN , d-Ce-alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cycloalkyl-Ci- C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from C1-C4 alkoxy, phenyl, benzyl and pyridyl, wherein the last three radicals may be unsubstituted, partially or fully halogenated and/or to carry 1 , 2 or 3 substituents selected from Ci- C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-

C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (C1-C6- alkoxy)carbonyl;

R ^18a , R ^18b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein each of the four aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R ⁷ ,

OR ^16a , S(0) _n R ^16a , -S(0) _n N R ^7a R ^7b , C(=0)R ¹⁵ , C(=0)OR ¹⁶ , C(=0)N R ^7a R ⁷ , C(=S)R ¹⁵ , C(=S)SR ^16a , C(=S)N R ^7a R ⁷ , C(=N R ⁷ ) R ¹⁵ ; phenyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ,

and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromaticC- bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,

or,

R ^18a and R ^18b are together a C2-C7 alkylene chain and form a 3-, 4-, 5-, 6-, 7- or 8- membered saturated, partly unsaturated or aromaticring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur or nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromaticC-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; the stereoisomers, tautomers and the salts thereof.

Moreover, the present invention relates to and includes the following embodiments:

agricultural and veterinary compositions comprising an amount of at least one compound of the formula (I) or a stereoisomer, tautomer or salt thereof;

the use of the compounds of formula (I), the stereoisomers, the tautomers or the salts thereof for combating invertebrate pests;

the use of the compounds of formula (I), the stereoisomers, the tautomers or the salts thereof for protecting growing plants from attack or infestation by invertebrate pests;

the use of the compounds of formula (I), the stereoisomers, the tautomers or the salts, thereof for protecting plant proparagation material, especially seeds, from soil insects; the use of the compounds of formula (I), the stereoisomers, the tautomers or the salts thereof for protecting the seedlings roots and shoots of plants from soil and foliar insects; a method for combating or controlling invertebrate pests, which method comprises contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound of the formula (I) or a stereoisomer, a tautomer or salt thereof;

a method for protecting growing plants from attack or infestation by invertebrate pests, which method comprises contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one compound of the formula (I) or a stereoisomer, a tautomer or salt thereof, in particular a method protecting crop plants from attack or infestation by animal pests, which comprises contacting the crop plants with a pesticidally effective amount of at least one compound of the formula (I) or stereoisomer, a tautomer or salt thereof;

- a method for the protection of plant propagation, especially seeds, from soil insects and of the seedlings' roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermination with at least one compound of the formula (I) or stereoisomer, a tautomer or salt thereof;

seeds comprising a compound of the formula (I) or an enantiomer, diastereomer or salt thereof;

the use of compounds of formula (I), the stereoisomers, the tautomers or the salts, in particular the veterinary acceptable salts, thereof for combating parasites in and on animals, in particular for the use in the treatment of animals infested or infected by parasites, for preventing animals of getting infected or infested by parasites or for protecting animals against infestation or infection by parasites;

a method for treating animals infested or infected by parasites or preventing animals of getting infected or infested by parasites or protecting animals against infestation or infection by parasites which comprises administering or applying to the animals a parasiticidally effective amount of a compound of formula (I) or the stereoisomers and/or salts, in particular veterinary acceptable salts, thereof;

a process for the preparation of a veterinary composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises formulating a compound of formula (I) or a stereoisomer, tautomer and/or veterinary acceptable salt thereof with a carrier composition suitable for veterinary use; - the use of a compound of formula (I) or the stereoisomers, tautomers and/or veterinary acceptable salt thereof for the preparation of a medicament for treating, controlling, preventing or protecting animals against infestation or infection by parasites.

The present invention also relates to plant propagation materials, in particular as mentioned above to seeds, containing at least one compound of formula (I), a stereoisomer, a tautomer and/or an agriculturally acceptable salt thereof.

Detailed Description of Invention

The present invention relates to every possible stereoisomer of the compounds of formula (I), i.e. to single enantiomers, diastereomers and E/Z-isomers as well as to mixtures thereof and also to the salts thereof. The present invention relates to each isomer alone, or mixtures or combinations of the isomers in any proportion to each other. 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 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

enantiomers or diastereomers of the compound I or its mixtures. Suitable compounds of the formula (I) also include all possible geometrical stereoisomers (cis/trans isomers, E/Z-isomers) and mixtures thereof, in particular the E/Z-isomers with regard to the C=N double bond in formula (I).

The present invention also relates to potential tautomers of the compounds of formula (I) and also to the salts of such tautomers. The present invention relates to the tautomer as such as well as to mixtures or combinations of the tautomers in any proportion to each other. The term "tautomers" encompasses isomers, which are derived from the compounds of formula (I) by the shift of an H-atom involving at least one H-atom located at a nitrogen, oxygen or sulphur atom. Examples of tautomeric forms are keto-enol forms, imine-enamine forms, urea-isourea forms, thiourea-isothiourea forms, (thio)amide-(thio)imidate forms etc.

The compounds of the present invention, i.e. the compounds of formula (I), their stereoisomers, their tautomers as well as their salts, in particular their agriculturally acceptable salts and their veterinarily acceptable salts, may be amorphous or may exist in one ore more different crystalline states (polymorphs) or modifications 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 or modifications of the respective

stereoisomers or tautomers, as well as amorphous or crystalline salts thereof.

Salts of the compounds of the formula (I) are preferably agriculturally salts as well as 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 or veterinary useful salts are especially the salts of those cations or anions, in particular 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-C ₄ -alkyl, Ci-C ₄ -hydroxyalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -alkoxy-Ci-C ₄ -alkyl, hydroxy-Ci- C ₄ -alkoxy-Ci-C ₄ -alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2- hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl-ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4- alkyl)sulfoxonium.

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

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

"Halogen" will be taken to mean fluoro, chloro, bromo and iodo.

The term "partially or completely halogenated" will be taken to mean that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine. For example, partially or completely halogenated alkyl is also termed haloalkyl, partially or completely halogenated cycloalkyl is also termed halocycloalkyl, partially or completely halogenated alkylenyl is also termed haloalkenyl, partially or completely halogenated alkylynyl is also termed haloalkynyl, partially or completely halogenated alkoxy is also termed haloalkoxy, partially or completely halogenated alkylthio is also termed haloalkthio, partially or completely halogenated alkylsulfinyl is also termed haloalkylsulfinyl, partially or completely halogenated alkylsulfonyl is also termed haloalsulfonyl, partially or completely halogenated cycloalkylalkyl is also termed halocycloalkylalkyl.

The term "C _n -C _m -alkyl" as used herein, and also in C _n -C _m -alkylamino, di-C _n -C _m -alkylamino, Cn-Cm-alkylaminocarbonyl, di-(C _n -C _m -alkylamino)carbonyl, C _n -C _m -alkylthio , C _n -C _m -alkylsulfinyl and C _n -C _m -alkylsulfonyl, refers to a branched or unbranched saturated hydrocarbon group having n to m, e.g. 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 - methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, hexyl, 1 ,1 - dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3- dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2- trimethylpropyl, 1 -ethyl-1 -methylpropyl, 1 -ethyl-2-methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers. Ci-C4-alkyl means for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl or 1 ,1 -dimethylethyl.

The term "C _n -C _m -haloalkyl" as used herein, and also in C _n -C _m -haloalkylthio (= C _n -C _m - haloalkylsulfenyl), C _n -C _m -haloalkylsulfinyl and C _n -C _m -haloalkylsulfonyl, refers to a straight-chain or branched alkyl group having n to m carbon atoms, e.g. 1 to 10 in particular 1 to 6 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example Ci-C4-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 - bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2- fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl,

pentafluoroethyl and the like. The term Ci-Cio-haloalkyl in particular comprises C1-C2- fluoroalkyl, which is synonym with methyl or ethyl, wherein 1 , 2, 3, 4 or 5 hydrogen atoms are substituted by fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoromethyl. "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.

Similarly, "C _n -C _m -alkoxy", "C _n -C _m -alkylthio", or "C _n -C _m -alkylsulfenyl", respectively, "C _n -C _m - alkylsulfinyl" or "C _n -C _m -alkylsulfonyl" refer to straight-chain or branched alkyl groups having n to m carbon atoms, e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as mentioned above) bonded through O, S, S(=0) or S(=0)2 linkages, respectively, at any bond in the alkyl group. Accordingly, the terms "C _n -C _m -haloalkoxy", "C _n -C _m -haloalkylthio" or "Cn-Cm-alkylsulfenyl", respectively, "C _n -C _m -haloalkylsulfinyl" or "C _n -C _m -haloalkylsulfonyl", refer to straight-chain or branched alkyl groups having n to m carbon atoms, e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as mentioned above) bonded through O, S, S(=0) or S(=0)2 linkages, respectively, at any bond in the haloalkyl group, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.

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

The term "C _n -C _m -alkylthio" is a C _n -C _m -alkyl group, as defined above, attached via a sulfur atom. Ci-C2-Alkylthio is methylthio or ethylthio. Ci-C4-Alkylthio is, for example, methylthio, ethylthio, n-propylthio, 1 -methylethylthio (isopropylthio), butylthio, 1 -methylpropylthio (sec- butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1 -dimethylethylthio (tert-butylthio). C1-C6- Alkylthio includes the meanings given for Ci-C4-alkylthio and also includes, 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-l -methylpropylthio or 1-ethyl-2-methylpropylthio. Ci-Cs-Alkylthio includes the meanings given for Ci-C6-alkylthio and also includes, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof. Ci-Cio-Alkylthio includes the meanings given for Ci-Cs-alkylthio and also includes, for example, nonylthio, decylthio and positional isomers thereof.

The term "C _n -C _m -a I kylsu If i nyl" is a C _n -C _m -alkyl group, as defined above, attached via a S(=0) group. The term "C _n -C _m -alkylsulfonyl" is a C _n -C _m -alkyl group, as defined above, attached via a S(=0)2 group.

The term "C _n -C _m -haloalkyloxy" is a C _n -C _m -haloalkyl group, as defined above, attached via an oxygen atom. Examples include Ci-C2-haloalkoxy, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1 -chloroethoxy, 1 - bromoethoxy, 1 -fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro- 2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy and pentafluoroethoxy.

The term "C _n -C _m -haloalkylthio" is a C _n -C _m -haloalkyl group, as defined above, attached via a sulfur atom. Examples include Ci-C2-haloalkylthio, such as chloromethylthio,

bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1 - chloroethylthio, 1 -bromoethylthio, 1 -fluoroethylthio, 2-fluoroethylthio, 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 and pentafluoroethylthio and the like.

Similarly the terms Ci-C2-fluoroalkoxy and Ci-C2-fluoroalkylthio refer to Ci-C2-fluoroalkyl which is bound to the remainder of the molecule via an oxygen atom or a sulfur atom, respectively.

The term "C _n -C _m -haloalkylsulfinyl" is a C _n -C _m -haloalkyl group, as defined above, attached via a S(=0) group. The term "C _n -C _m -haloalkylsulfonyl" is a C _n -C _m -haloalkyl group, as defined above, attached via a S(=0)2 group.

The term "C2-C _m -alkenyl" as used herein denotes a linear or branched ethylenically unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2 to 6 carbon atoms and a C=C- double bond in any position, such as ethenyl, 1 -propenyl, 2-propenyl, 1 -methyl-ethenyl, 1 - butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2- methyl-2-propenyl, 1 -pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl-1 -butenyl, 2-methyl- 1 -butenyl, 3-methyl-1 -butenyl, 1 -methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1 - methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 ,1 -dimethyl-2-propenyl, 1 ,2-dimethyl- 1 -propenyl, 1 ,2-dimethyl-2-propenyl, 1 -ethyl-1 -propenyl, 1 -ethyl-2-propenyl, 1 -hexenyl, 2- hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1 -methyl-1 -pentenyl, 2-methyl-1 -pentenyl, 3-methyl- 1 -pentenyl, 4-methyl-1 -pentenyl, 1 -methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2- pentenyl, 4-methyl-2-pentenyl, 1 -methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1 -methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl- 4-pentenyl, 1 ,1 -dimethyl-2-butenyl, 1 ,1 -dimethyl-3-butenyl, 1 ,2-dimethyl-1 -butenyl, 1 ,2-dimethyl-

2- butenyl, 1 ,2-dimethyl-3-butenyl, 1 ,3-dimethyl-1 -butenyl, 1 ,3-dimethyl-2-butenyl, 1 ,3-dimethyl-

3- butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1 -butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl- 3-butenyl, 3,3-dimethyl-1 -butenyl, 3,3-dimethyl-2-butenyl, 1 -ethyl-1 -butenyl, 1 -ethyl-2-butenyl, 1 - ethyl-3-butenyl, 2-ethyl-1 -butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1 ,1 ,2-trimethyl-2- propenyl, 1 -ethyl-1 -methyl-2-propenyl, 1 -ethyl-2-methyl-1 -propenyl and 1 -ethyl-2-methyl-2- propenyl.

The term "C2-C _m -haloalkenyl" as used herein, which is also expressed as "C2-C _m -alkenyl which is partially or completely halogenated", refers to C2-C _m -alkenyl, 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 1 -fluoroethenyl, 2-fluoroethenyl, 2,2- difluoroethenyl, 1 ,2,2-trifluoroethenyl, 1 -fluoro-2-propenyl, 2-fluoro-2-propenyl, 3-fluoro-2- propenyl, 1 -fluoro-1 -propenyl, 1 ,2-difluoro-1 -propenyl, 3,3-difluoropropen-2-yl, 1 -chloroethenyl, 2-chloroethenyl, 2,2,-dichloroethenyl, 1 -chloro-2-propenyl, and the like.

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

The term "C2-C _m -haloalkynyl" as used herein, which is also expressed as "C2-C _m -alkynyl which is partially or completely halogenated", refers to C2-C _m -alkynyl, 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. Examples of C2-C _m -haloalkynyl include 1 -fluoro-2- propenyl, 2-fluoro-2-propenyl, 3-fluoro-2-propenyl, 1 -fluoro-2-propynyl and 1 ,1 -difluoro-2- propenyl, and the like.

The term "C3-C _m -cycloalkyl" as used herein refers to a monocyclic and polycyclic 3- to m- membered saturated cycloaliphatic radical, e.g. cyclopropyl, cydobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, bicyclo[2.2.1]heptyl, bicyclo[3.1 .1 ]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1 ]octyl. Preferably, the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical.

The term "C3-C _m -cycloalkenyl" as used herein refers to a monocyclic and polycyclic 3- to m-membered unsaturated cycloaliphatic radical, e.g. cyclopropenyl, cyclobutenyl,

cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclodecenyl, bicyclo[2.2.1 ]heptenyl, bicyclo[3.1 .1]heptenyl, bicyclo[2.2.2]octenyl and bicyclo[3.2.1]octenyl. Preferably, the term cycloalkenyl denotes a monocyclic unsaturated hydrocarbon radical.

The term "C3-C _m -halocycloalkyl" as used herein, which is also expressed as "cycloalkyl which is partially or completely halogenated", refers C3-C _m -cycloalkyl 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. Examples of C3-C _m -halocycloalkyl include 1 - fluorocycloprpyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 1 -chlorocyclcopropyl, 2- chlorocyclopropyl, 2,2-dichlorocyclopropyl, 2,3-difluorocyclopropyl, 1 -fluorocycobutyl etc.

The term "C3-C _m -cycloalkyl-Ci-C4-alkyl" refers to a C3-C _m -cycloalkyl group as defined above, which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above. Examples for C3-C _m -cycloalkyl-Ci-C4-alkyl are cyclopropyl methyl, cyclopropylethyl, cyclopropylpropyl, cyclobutyl methyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl.

The term "C3-C _m -halocycloalkyl-Ci-C4-alkyl" refers to a C3-C _m -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-C4-alkoxy-Ci-C4-alkyl" as used herein refers to alkyl having 1 to 4 carbon atoms, e.g. like specific examples mentioned above, wherein one hydrogen atom of the alkyl radical is replaced by an Ci-C4-alkoxy group. Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert- butoxymethyl, 1 -methoxyethyl, 1 -ethoxyethyl, 1 -propoxyethyl, 1 -isopropoxyethyl, 1 -n- butoxyethyl, 1 -sec-butoxyethyl, 1 -isobutoxyethyl, 1 -tert-butoxyethyl, 2-methoxyethyl, 2- ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2- isobutoxyethyl, 2-tert-butoxyethyl, 1 -methoxypropyl, 1 -ethoxypropyl, 1 -propoxypropyl, 1 - isopropoxypropyl, 1 -n-butoxypropyl, 1 -sec-butoxypropyl, 1 -isobutoxypropyl, 1 -tert-butoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-isopropoxypropyl, 2-n-butoxypropyl, 2- sec-butoxypropyl, 2-isobutoxypropyl, 2-tert-butoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3- propoxypropyl, 3-isopropoxypropyl, 3-n-butoxypropyl, 3-sec-butoxypropyl, 3-isobutoxypropyl, 3- tert-butoxypropyl and the like.

The term Ci-C4-haloalkoxy-Ci-C4-alkyl is a straight-chain or branched alkyl group having from 1 to 4 carbon atoms, wherein one of the hydrogen atoms is replaced by a Ci-C4-alkoxy group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remaining hydrogen atoms, either in the alkoxy moiety or in the alkyl moiety or in both, are replaced by halogen atoms. Examples are difluoromethoxymethyl (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 "C _n -C _m -alkoxycarbonyl" is a C _n -C _m -alkoxy group, as defined above, attached via an carbonyl group atom. Ci-C2-Alkoxycarbonyl is methoxycarbonyl or ethoxycarbonyl. C1-C4- Alkoxy is, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1 - methylethoxycarbonyl, butoxycarbonyl, 1 -methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1 ,1 -dimethylethoxycarbonyl. Ci-C6-Alkoxycarbonyl includes the meanings given for C1-C4- alkoxycarbonyl and also includes, for example, pentoxycarbonyl, 1 -methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 1 ,1 -dimethylpropoxycarbonyl, 1 ,2- dimethylpropoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1 -ethylpropoxycarbonyl,

hexoxycarbonyl, 1 -methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1 ,1 -dimethylbutoxycarbonyl, 1 ,2-dimethylbutoxycarbonyl,

1 ,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl,

3,3-dimethylbutoxycarbonyl, 1 -ethylbutoxy, 2-ethylbutoxycarbonyl, 1 ,1 ,2- trimethylpropoxycarbonyl, 1 ,2,2-trimethylpropoxycarbonyl, 1 -ethyl-1 -methylpropoxycarbonyl or 1 -ethyl-2-methylpropoxycarbonyl. The term "aryl" as used herein refers to an aromatic hydrocarbon radical such as naphthyl or in particular phenyl.

The term "3- to 6-membered carbocyclic ring" as used herein refers to cyclopropane, cyclobutane, cyclopentane and cyclohexane rings. The term "3- to 7-membered carbocyclic ring" as used herein refers to cyclopropane, cyclobutane, cyclopentane, cyclohexane and cycloheptane rings.

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

Examples of 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic rings include: oxiranyl, aziridinyl, azetidinyl, 2 tetrahydrofuranyl, 3-tetrahydrofuranyl, 2 tetrahydrothienyl, 3

tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3 pyrazolidinyl, 4 pyrazolidinyl, 5-pyrazolidinyl, 2 imidazolidinyl, 4 imidazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5 oxazolidinyl, 3-isoxazolidinyl, 4 isoxazolidinyl, 5 isoxazolidinyl, 2 thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 3 isothiazolidinyl, 4- isothiazolidinyl, 5 isothiazolidinyl, 1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4 oxadiazolidin 5 yl, 1 ,2,4- 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-2-yl, 2-tetrahydropyranyl, 4 tetrahydropyranyl, 1 ,3-dioxan-5- yl, 1 ,4-dioxan-2-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-hexahydropyridazinyl, 4 hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5 hexahydropyrimidinyl, 2-piperazinyl, 1 ,3,5-hexahydrotriazin-2-yl and 1 ,2,4 hexahydrotriazin-3-yl, 2-morpholinyl, 3- morpholinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 1 -oxothiomorpholin-2-yl, 1 -oxothiomorpholin- 3-yl, 1 ,1 -dioxothiomorpholin-2-yl, 1 ,1 -dioxothiomorpholin-3-yl, hexahydroazepin-1 -, -2-, -3- or -4- yl, hexahydrooxepinyl, hexahydro-1 ,3-diazepinyl, hexahydro-1 ,4-diazepinyl, hexahydro-1 ,3- oxazepinyl, hexahydro-1 ,4-oxazepinyl, hexahydro-1 ,3-dioxepinyl, hexahydro-1 ,4-dioxepinyl and the like. Examples of 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclic rings include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3- dihydrothien-2-yl, 2,3 dihydrothien-3-yl, 2,4 dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2- yl, 2-pyrrolin-3-yl, 3 pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4 isoxazolin 3 yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2 isoxazolin-5-yl, 3-isoxazolin-5-yl, 4- isoxazolin-5-yl, 2-isothiazolin-3-yl, 3 isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3- isothiazolin-4-yl, 4 isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3 dihydropyrazol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3 dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1 -yl, 3,4 dihydropyrazol-3-yl, 3,4-dihydropyrazol-4- yl, 3,4-dihydropyrazol-5-yl, 4,5 dihydropyrazol-1 -yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol- 4-yl, 4,5 dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3 dihydrooxazol- 4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4 dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 3,4-dihydrooxazol-5-yl, 3,4 dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4 di- or tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5 di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1 ,3,5-di- or tetrahydrotriazin-2-yl, 1 ,2, 4-di- or tetrahydrotriazin-3-yl, 2,3,4,5-tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6- tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7 tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5- , -6- or -7-yl, 2,3,6,7 tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydrooxepinyl, such as 2,3,4, 5-tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7 tetrahydro[1 H]oxepin-2- , -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7 tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydro-1 ,3- diazepinyl, tetrahydro-1 ,4-diazepinyl, tetrahydro-1 ,3-oxazepinyl, tetrahydro-1 ,4-oxazepinyl, tetrahydro-1 ,3-dioxepinyl and tetrahydro-1 ,4-dioxepinyl.

Examples of 5- or 6-membered aromatic heterocyclic rings, also termed heteroaromatic rings or hetaryl, include: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4- pyrazo-"lyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4 thiazolyl, 5-thiazo-"lyl, 2- imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4- pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.

A "Ci-Cm-alkylene" is divalent branched or preferably non-branched or linear saturated aliphatic chain having 1 to m, e.g. 1 to 7 carbon atoms, for example Chb, CH2CH2, -CH(CH3)-, CH2CH2CH2, CH(CH ₃ )CH ₂ , CH ₂ CH(CH ₃ ), CH2CH2CH2CH2, CH2CH2CH2CH2CH2,

CH2CH2CH2CH2CH2CH2, and CH2CH2CH2CH2CH2CH2CH2.

Embodiments of the present invention as well preferred compounds of the present invention are outlined in the following paragraphs. The remarks made below concerning preferred embodiments of the variables of the compounds of formula (I), especially with respect to their substituents X, Het, R ¹ ,R ² , R ^3a , R ^3b , R ⁴ , including the variables R ^4a , R ^4b , R ^4c and R ^4d , as well as R ⁶ and the variable k are valid both on their own and, in particular, in every possible combination with each other.

When # appears in a formula showing a preferred substructure of a compound of the present invention, it denotes the attachment bond in the remainder molecule.

Preferred are compounds of formula (I), wherein Het is selected from the group consisting of radicals of formulae Het-1 to Het-24, with preference given to compounds of the formula (I), their stereoisomers, there tautomers and their salts, where Het is selected from the radicals of the formulae Het-1 , Het-1 1 and Het-24:

Het-6 Het-7 Het-8 Het-9 Het-10

Het-11 Het-12 Het-13 Het-14 Het-15

Het-16 Het-17 Het-18 Het-19 Het-20

Het-21 Het-22 Het-23 Het-24 wherein # denotes the bond in formula (I), and wherein R ⁶ and k are as defined above and where R ^6a is hydrogen or has one of the meanings given for R ⁶ and where R ^6b is hydrogen or a C-bound radical mentioned as R ⁶ and where R ^6b is in particular hydrogen, Ci-C4-alkyl or C1-C4- haloalkyl. In particular k is 0, 1 or 2, especially 0 or 1 . In formulae Het-1 , Het-2, Het-3, Het-4, Het-7, Het-8, Het-9, Het-10, Het-1 1 , Het-18 and Het-21 , k is especially 1. In particular R ^6a in formulae Het-12, Het-13, Het-14, Het-16, Het-17, Het-19, Het 20 and Het-22 is different from hydrogen.

Irrespectively of its occurrence, R ⁶ is preferably selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein each of the four last mentioned radicals may optionally be partly or completely halogenated, in particular by fluorine or chlorine, or may be (further) substituted independently from one another with one or more (e.g. 1 , 2 or 3) identical or different R ⁷ , or R ⁶ may also be a radical selected from the group consisting of OR ⁸ , NR ^17a R ^17b , S(0) _n R ^8a , S(0) _n NR ^7a R ^7b , C(=0)R ^7a , C(=0)NR ^7a R ⁷ , C(=0)OR ⁸ , C(=S)R ^7a , C(=S)NR ^7a R ⁷ , C(=NR ⁷ )R ^7a , C(=NR ⁷ )NR ^7a R ⁷ . Irrespectively of its occurrence, R ⁶ is in particular selected from the group consisting of halogen, such as chlorine or fluorine, C1-C4- alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl,

trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, C1-C2- alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl. Irrespectively of its occurrence, R ^6a is preferably selected from the group consisting of hydrogen, halogen, cyano, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may optionally be partly or completely halogenated, in particular by fluorine or chlorine, or may further substituted independently from one another with one or more identical or different R ⁷ , or R ^6a may also be a radical selected from the group consisting of OR ⁸ , N R ^17a R ^17b , S(0) _n R ^8a , S(0) _n N R ^7a R ^7b , C(=0)R ^7a , C(=0)N R ^7a R ^7b , C(=0)OR ⁸ , C(=S)R ^7a , C(=S)N R ^7a R ^7b ,

C(=N R ¹⁷ )R ^7a , C(=N R ¹⁷ )N R ^17a R ^17b . Irrespectively of its occurrence, R ^6a is in particular selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, C1-C4- alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.

Irrespectively of its occurrence, R ^6b is in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl or ethyl, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably C1-C2- alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.

Particularly preferred are compounds of formula (I), wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24,

Het-1 Het-11a Het-24 wherein # denotes the bond in formula (I), and where

R ⁶ is selected from the group consisting of halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl; and where

R ^6a is selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, C1-C4- haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl and k is 0, 1 or 2.

A particularly preferred group of embodiments relates to compounds of formula (I) to the stereoisomers, the tautomers and to the salts thereof, wherein Het is a radical of formula Het-1 , where k is 0, 1 or 2, in particular 1 or 2 and especially 1 and where R ⁶ is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, C1-C4- alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl,

trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, C1-C2- alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl. Amongst the compounds of this particular group of embodiments, a particular sub-group of embodiments relates to compounds of the formula (I), to the stereoisomers, the tautomers and to the salts thereof, wherein Het is a radical of formula Het-1 a

wherein # denotes the bond in formula (I), and where

R ⁶ is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, and even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl or pentafluoroethyl;

R ^6a is as defined above and in particular selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine and Ci-C4-alkyl, such as methyl or ethyl, more preferably is hydrogen or halogen, in particular hydrogen.

A special embodiment of the radical Het-1 a is 6-chloropyridin-3-yl, i.e. R ^6a is hydrogen and R ⁶ is chlorine. A further special embodiment of the radical Het-1 a is 6-(trifluoromethyl)pyridin-3- yl, i.e. R ^6a is hydrogen and R ⁶ is trifluoromethyl.

Another particularly preferred group of embodiments relates to compounds of formula (I) to the stereoisomers, the tautomers and to the salts thereof, wherein Het is a radical of formula Het-1 1 , where k is 0, 1 or 2, in particular 0 or 1 , and where Het is in particular a radical of formula Het-1 1 a,

wherein # denotes the bond in formula (I), and where R ^6a is as defined above and wherein R ^6a is in particular selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, C1-C4- haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl. A special embodiment of the radical Het-1 1 a is 2-chlorothiazol-5-yl, i.e. R ^6a is chlorine.

Another particularly preferred group of embodiments relates to compounds of formula (I) to the stereoisomers, the tautomers and to the salts thereof, wherein Het is a radical of formula Het-24, where k is 0, 1 or 2, in particular 0 or 1 , and where R ⁶ , if present, is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, Ci- C4-alkyl, such as methyl or ethyl, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, and even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.

Preferred are compounds of formula (I), wherein R ¹ and R ² are independently from each other selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl or isopropyl, C3-C6- cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or C3-C6-halocycloalkyl such as 1 -fluorocyclopropyl or 2,2- difluorocyclopropyl.

Preferred are also compounds of formula (I), wherein R ¹ and R ² form, together with the carbon atom, which they attached to, a 3- to 5 membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl or cyclopentyl.

Preferred are also compounds of formula (I), wherein R ¹ and R ² together are =CR ¹³ R ¹⁴ . Even more preferred are compounds of formula (I), wherein R ¹ and R ² are independently from each other selected from the group consisting of hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl.

Preferably at least one of the radicals R ¹ and R ² is hydrogen.

Even more preferred are compounds of formula (I), wherein R ¹ and R ² are both hydrogen or R ¹ is methyl and R ² is hydrogen.

In a particular group of embodiments, R ¹ and R ² are both hydrogen. A group of embodiments relates to compounds of formula (I), wherein R ^3a is different from hydrogen. Another group of embodiments relates to compounds of formula (I), wherein R ^3a is hydrogen.

Preferably, R ^3a is a C-bound radical, in particular

- Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R ⁷ ,

C3-C6-cycloalkyl, which is unsubstituted or carries any combination of 1 , 2, 3, 4 or 5 radicals R ¹⁰ , or

Cyc ¹ -Q ¹ , where

Cyc ¹ is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , Q ¹ is Ci-C ₄ -alkanediyl or C ₂ -C ₄ -alkenediyl, in particular CH ₂ , CH ₂ CH ₂ or CHCH ₃ .

In the context of R ^3a , the variable R ⁷ is in particular selected from the group consisting of N0 ₂ , CN, Cs-Ce-cycloalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, =N-0-Ci-C ₄ -alkyl, Ci-C ₄ -alkylthio, Ci-C ₄ -alkylsulfinyl and Ci-C ₄ -alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and especially selected from the group consisting of N0 ₂ , CN, cyclopropyl and Ci-C ₄ -alkoxy.

In the context of R ^3a , the variable R ¹⁰ is in particular selected from the group consisting of halogen, N0 ₂ , CN, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, Ci-C ₄ -alkylthio, Ci-C ₄ -alkylsulfinyl and Ci- C ₄ -alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely

halogenated, and especially selected from the group consisting of halogen, such as fluorine or chlorine, N0 ₂ , CN and Ci-C ₄ -alkoxy, such as methoxy or ethoxy.

In the context of R ^3a , the variable Cyc ¹ is in particular selected from the group consisting of phenyl and 5- or 6-membered hetaryl, such as pyridiyl, wherein phenyl and hetaryl are unsubstituted or carry 1 , 2, 3, 4 or 5 radicals R ¹⁰ , as defined above, which are in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, N0 ₂ , CN, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, Ci-C ₄ -alkylthio, Ci-C ₄ -alkylsulfinyl and Ci-C ₄ -alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and especially selected from the group consisting of N0 ₂ , CN and Ci-C ₄ -alkoxy. Cyc ¹ is especially phenyl, which is unsubstituted or carries 1 , 2 or 3 radicals R ¹⁰ , as defined above, which are in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, N0 ₂ , CN, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, Ci-C ₄ -alkylthio, Ci-C ₄ -alkylsulfinyl and Ci-C ₄ -alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated.

In particular, R ^3a is Ci-C6-alkyl or Ci-C6-haloalkyl, in particular Ci-C3-alkyl or C1-C3- haloalkyl, where alkyl and haloalkyl may further carry any combination of 1 , 2 or 3 radicals R ⁷ , or C3-C6-cycloalkyl, especially cyclopropyl, where C3-C6-cycloalkyl is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen and Ci-C ₄ -alkyl. In this context, R ⁷ is as defined above and in particular from the group consisting of N0 ₂ , CN, C3-C6-cycloalkyl, Ci-C ₄ -alkoxy, C1-C4- haloalkoxy, =N-0-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and R ⁷ is especially selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy.

Especially, R ^3a is selected from the group consisting of methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropyl, cyclopropylmethyl, CH2CN, CH2CH2CN, CH2NO2 and CH2CH2NO2.

Another group of embodiments relates to compounds of formula (I), wherein R ^3a is a radical, which is selected from the group consisting of C(=0)NR ^9a R ^9b , C(=S)NR ^9a R ^9b ,

C(=0)OR ⁸ , C(=0)R ^7a , C(=S)R ^7a and S(0) _n R ^8a . In the context of this embodiment, the radicals R ^7a , R ⁸ , R ^8a , R ^9a and R ^9b are as defined above or have in particular the following meanings: R ^7a is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R ¹⁰ ;

R ⁸ is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkylcarbonyl,

Ci-C4-haloalkylcarbonyl, Ci-C4-alkoxycarbonyl,

NH2-C(0), Ci-C4-alkylaminocarbonyl, di-(Ci-C4-alkyl)aminocarbonyl, phenyl, benzyl, where the phenyl ring in the last two mentioned radicals is unsbustituted or carries 1 , 2, 3 or 4 radicals R ¹⁰ , phenylcarbonyl, phenoxycarbonyl, wherein the last two radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2, SCN, SF ₅ , OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl and phenylaminocarbonyl, wherein the last mentioned radical may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;

R ^8a is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R ¹⁰ ;

R ^9a is selected from the group consisting of hydrogen, Ci-C4-alkyl and phenyl, which is

unsubstituted or carries 1 , 2, 3 or 4 radicals R ¹⁰ ;

R ^9b is selected from the group consisting of hydrogen, Ci-C4-alkyl and phenyl, which is

unsubstituted or carries 1 , 2, 3 or 4 radicals R ¹⁰ .

In the context of radicals R ^7a , R ⁸ , R ^8a , R ^9a and R ^9b the radical R ¹⁰ is in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, NO2, CN, Ci- C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated.

Preferably, R ^3b is a C-bound radical, in particular

Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R ⁷ , C3-C6-cycloalkyl, which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R ¹⁰ , or

Cyc ² -Q ² , where

Cyc ² is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different

heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , Q ² is Ci-C ₄ -alkanediyl or C ₂ -C ₄ -alkenediyl, in particular CH ₂ , CH ₂ CH ₂ or CHCH ₃ . In the context of R ^3b , the variable R ⁷ is in particular selected from the group consisting of

N0 ₂ , CN, Cs-Ce-cycloalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, =N-0-Ci-C ₄ -alkyl, Ci-C ₄ -alkylthio, Ci-C ₄ -alkylsulfinyl and Ci-C ₄ -alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and especially selected from the group consisting of N0 ₂ , CN, cyclopropyl and Ci-C ₄ -alkoxy.

In the context of R ^3b , the variable R ¹⁰ is in particular selected from the group consisting of halogen, N0 ₂ , CN, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, Ci-C ₄ -alkylthio, Ci-C ₄ -alkylsulfinyl and Ci- C ₄ -alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely

halogenated, and especially selected from the group consisting of halogen, such as fluorine or chlorine, N0 ₂ , CN and Ci-C ₄ -alkoxy, such as methoxy or ethoxy.

In the context of R ^3b , the variable Cyc ² is in particular selected from the group consisting of phenyl and 5- or 6-membered hetaryl, such as pyridiyl, wherein phenyl and hetaryl are unsubstituted or carry 1 , 2, 3, 4 or 5 radicals R ¹⁰ , as defined above, which are in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, N0 ₂ , CN, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, Ci-C ₄ -alkylthio, Ci-C ₄ -alkylsulfinyl and Ci-C ₄ -alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and especially selected from the group consisting of N0 ₂ , CN and Ci-C ₄ -alkoxy. Cyc ² is especially phenyl, which is unsubstituted or carries 1 , 2 or 3 radicals R ¹⁰ , as defined above, which are in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, N0 ₂ , CN, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, Ci-C ₄ -alkylthio, Ci-C ₄ -alkylsulfinyl and Ci-C ₄ -alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated.

In particular, R ^3b is Ci-C6-alkyl or Ci-C6-haloalkyl, especially Ci-C3-alkyl or Ci-C3-haloalkyl, where alkyl and haloalkyl may carry 1 , 2 or 3 further radicals R ⁷ , which are identical or different. In this context, the radicals R ⁷ are as defined above and in particular from the group consisting of N0 ₂ , CN, Cs-Ce-cycloalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, =N-0-Ci-C ₄ -alkyl, Ci-C ₄ -alkylthio, Ci-C ₄ -alkylsulfinyl and Ci-C ₄ -alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and R ⁷ is especially selected from the group consisting of N0 ₂ , cyclopropyl, CN and Ci-C ₄ -alkoxy.

More particularly, R ^3b is selected from the group consisting of Ci-C3-alkyl and C1-C3- haloalkyl, especially from the group consisting of methyl, ethyl, difluoromethyl and

trifluoromethyl. In a particular group (1 ) of embodiments the variable R ⁴ is a radical R ^4a as defined above. In this group (1 ) of embodiments, the variable R ^4a is in particular selected from the group consisting of

Ci-Cio-alkyl, C2-Cio-alkenyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R ^5a ,

C3-C6-cycloalkyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ^10a ,

saturated 3-, 4-, 5- or 6-membered heterocyclyl, which carries 1 or 2 oxygen or nitrogen atoms as ring members and where heterocycyl is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ^10a , and

6-membered heteroaryl having 1 , 2 or 3 nitrogen atoms as ring members and where heteroaryl is unsubstituted or may be substituted with 1 , 2, 3 or 4 identical or different substituents R ¹⁰ ;

and in particular from the group consisting of

Ci-C6-alkyl, C2-C6-alkenyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 or 2 radicals R ^5a ,

C3-Cio-cycloalkyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ^10a , and

3-, 4-, 5- or 6-membered, saturated heterocyclyl, which carries 1 or 2 oxygen or nitrogen atoms as ring members and where heterocycyl is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ^10a .

In the context of the radical R ^4a , the variable R ^5a is as defined above and, irrespectively of its occurrence, has in particular one of the following meanings:

CN, N0 ₂ , OH, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, S(0) _n R ^8a , S(0) _n NR ^7a R ^7b , NR ^17a R ^17b ,

C(=0)NR ^7a R ^7b , C(=S)NR ^7a R ^7b , C(=0)OR ⁸ , C(=0)R ¹⁵ , NR ^7a -C(=0)R ^7a , NR ^7a -C(=0)OR ⁸ , NR ^17a -C(=0)NR ^17a R ^17b , phenyl or phenoxy, where the phenyl ring in the last two mentioned radicals is unsubstituted or carriers 1 , 2, 3, 4 or 5 radicals R ¹⁰ , or two R ^5a present on one carbon atom may together form =NOR ¹⁶ or =N-NR ^9a R ^9b .

In the context of the radical R ^4a , the variable R ^5a has more particularly one of the following meanings: CN, N0 ₂ , Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, S(0) _n R ^8a , S(0) _n NR ^7a R ⁷ , C(=0)OR ⁸ , C(=0)R ¹⁵ , or two R ^5a present on one carbon atom may together form =NOR ¹⁶ or

=N-NR ^9a R ^9b .

In the context of the radical R ^4a , the variable R ^5a is especially selected from the group consisting of CN, N0 ₂ , Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, S(0) _n R ^8a and S(0) _n NR ^17a R ¹⁷ .

In the context of group (1 ) of embodiments the variable R ¹⁰ is as defined above and, irrespectively of its occurrence, has in particular one of the following meanings:

halogen, CN, OH, SH, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, Ci-C ₄ -alkyl, Ci-C ₄ -haloalkyl, C1-C4- alkylcarbonyl, Ci-C ₄ -haloalkylcarbonyl, Ci-C ₄ -alkoxycarbonyl, NH2-C(0), Ci-C ₄ -alkylthio, C1-C4- alkylsulfonyl, Ci-C4-haloalkylthio, Ci-C4-haloalkylsulfonyl, SO2NH2, Ci-C4-alkylaminocarbony and di-(Ci-C4-alkyl)aminocarbonyl.

In the context of group (1 ) of embodiments the variable R ^10a is as defined above and, irrespectively of its occurrence, has in particular one of the following meanings:

halogen, CN, N0 ₂ , OH, SH, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, Ci-C ₄ -alkyl, Ci-C ₄ -haloalkyl, C1-C4- alkylcarbonyl, Ci-C ₄ -haloalkylcarbonyl, Ci-C ₄ -alkoxycarbonyl, NH ₂ -C(0), S(0) _n R ^8a , SO2NH2, Ci- C4-alkylaminocarbonyl and di-(Ci-C4-alkyl)aminocarbonyl, or two R ^10a present on one carbon atom may together form =NOR ^16a .

In a particular subgroup (V) of group (1 ) of embodiments the variable R ⁴ is different from trifluoromethyl.

In a further particular subgroup (1 ") of group (1 ) of embodiments the variable R ⁴ is different from Ci-C6-alkyl and Ci-C6-haloalkyl.

In a further particular subgroup (1 ^# ) of group (1 ) of embodiments the variable R ⁴ is different from Ci-C6-alkyl, Ci-C6-haloalkyl and phenyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ .

In the context of group (1 ) of embodiments the variables R ^7a , R ⁸ , R ^8a , R ^9a , R ^9b , R ¹⁰ , R ^10a , R ¹⁵ , R ¹⁶ , R ^16a , R ^17a , R ^17b , are as defined above and, irrespectively of their occurrence, have in particular one of the following meanings:

R ^7a is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6- cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R ¹⁰ , which are identical or different and in particular selected from the group consisting of halogen, OH, CN, NO2, Ci- C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;

R ⁸ is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkoxycarbonyl,

NH2-C(0), Ci-C4-alkylaminocarbonyl, di-(Ci-C4-alkyl)aminocarbonyl, phenyl, benzyl, where the phenyl ring in the last two mentioned radicals is unsbustituted or carries 1 , 2, 3 or 4 radicals R ¹⁰ , which are identical or different and in particular selected from the group consisting of halogen, OH, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (C1-C6- alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,

phenylcarbonyl, phenoxycarbonyl, wherein the last two radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N0 ₂ , SCN, SF ₅ , OH, Ci-C ₆ - alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci- C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (C1-C6- alkoxy)carbonyl, and

phenylaminocarbonyl, wherein the last mentioned radical may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;

R ^8a is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R ¹⁰ , which are identical or different and in particular selected from the group consisting of halogen, OH, CN, NO2, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (C1-C6- alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;

R ^9a is selected from the group consisting of hydrogen, Ci-C4-alkyl and phenyl, which is

unsubstituted or carries 1 , 2, 3 or 4 radicals R ¹⁰ , which are identical or different and in particular selected from the group consisting of halogen, OH, CN, NO2, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (C1-C6- alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;

R ^9b is selected from the group consisting of hydrogen, Ci-C4-alkyl and phenyl, which is

unsubstituted or carries 1 , 2, 3 or 4 radicals R ¹⁰ , which are identical or different and in particular selected from the group consisting of halogen, OH, CN, NO2, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C ₆ -alkoxy, Ci-C ₆ haloalkoxy, Ci-C ₆ -alkylthio, Ci-C ₆ -haloalkylthio, Ci-C ₆ - alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (C1-C6- alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;

R ¹⁰ is selected from the group consisting of halogen, CN, OH, SH, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci- C ₄ -alkoxycarbonyl, NH ₂ -C(0), Ci-C ₄ -alkylthio, Ci-C ₄ -alkylsulfonyl, Ci-C ₄ -haloalkylthio, Ci-

C4-haloalkylsulfonyl, SO2NH2, Ci-C4-alkylaminocarbony and di-(Ci-C4- alkyl)aminocarbonyl,;

R ^10a is selected from the group consisting of halogen, CN, NO2, OH, SH, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci- C ₄ -alkoxycarbonyl, NH ₂ -C(0), S(0) _n R ^8a , SO2NH2, Ci-C ₄ -alkylaminocarbonyl and di-(Ci-C ₄ - alkyl)aminocarbonyl, or

two R ^10a present on one carbon atom may together form =NOR ^16a ;

R ¹⁵ is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, (Ci-C6-alkyl)carbonyl and

(Ci-C6-alkoxy)carbonyl;

R ¹⁶ is selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl, where the two

aforementioned radicals are unsubstituted, partly or completely halogenated and/or may carry 1 or 2 radicals R ⁷ , which are as defined above and in particular selected from the group consisting of N0 ₂ , CN, OR ⁸ , S(0) _n R ^8a , NR ^17a R ^17b , C(=0)NR ^7a R ^7b , C(=0)OR ⁸ ,

C(=0)R ¹⁵ and NR ^7a -C(=0)R ^7a ; benzyl which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, N0 ₂ , Ci-Ce-alkyI, Ci-C ₆ -haloalkyl, Ci-Ce-alkoxy, Ci-C ₆ haloalkoxy, Ci-C ₆ -alkylthio, Ci C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;

R ^16a is selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl, where the two

aforementioned radicals are unsubstituted, partly or completely halogenated;

benzyl which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, N0 ₂ , Ci-Ce-alkyI, Ci-C ₆ -haloalkyl, Ci-Ce-alkoxy, Ci-C ₆ haloalkoxy, Ci-C ₆ -alkylthio, Ci C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;

R ^17a , R ^17b are each independently from one another selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, phenyl and benzyl, where the phenyl ring in the last two substitutents is unsbustituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, N0 ₂ , Ci-Ce-alkyI, Ci-C ₆ -haloalkyl, Ci-Ce-alkoxy, Ci-C ₆ haloalkoxy, (d- C6-alkyl)carbonyl and (Ci-C6-alkoxy)carbonyl.

In the context of group (1 ) of embodiments the variables R ^7a , R ⁸ , R ^8a , R ^9a , R ^9b , R ¹⁰ , R ^10a , R ¹⁵ , R ¹⁶ , R ^16a , R ^17a , R ^17b , irrespectively of their occurrence, have especially one of the following meanings:

R ^7a is selected from the group consisting of Ci-C4-alkyl or Ci-C4-haloalkyl;

R ⁸ is selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl;

R ^8a is selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl;

R ^9a is selected from the group consisting of hydrogen and Ci-C ₄ -alkyl;

R ^9b is selected from the group consisting of hydrogen and Ci-C ₄ -alkyl;

R ¹⁰ is selected from the group consisting of halogen, CN, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci

C ₄ -alkyl, Ci-C ₄ -haloalkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylthio and Ci-

C4-haloalkylsulfonyl;

R ^10a is selected from the group consisting of halogen, CN, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci C ₄ -alkyl, Ci-C ₄ -haloalkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylthio and Ci- C4-haloalkylsulfonyl;

R ¹⁵ is selected from the group consisting of hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl;

R ¹⁶ is selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl, where the two

aforementioned radicals are unsubstituted, partly or completely halogenated and/or may carry 1 or 2 radicals R ⁷ , which are as defined above and in particular selected from the group consisting of N0 ₂ , CN, OR ⁸ , S(0) _n R ^8a , NR ^17a R ^17b , C(=0)NR ^7a R ⁷ , C(=0)OR ⁸ , C(=0)R ¹⁵ and NR ^7a -C(=0)R ^7a , and

benzyl which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, N0 ₂ , d-Ce-alkyl, d-Ce-haloalkyl, Ci-Ce-alkoxy, d-C ₆ haloalkoxy, Ci-C ₆ -alkylthio, C C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl; R ^16a is selected from the group consisting of Ci-C6-alkyl and C2-C6-alkenyl, where the two aforementioned radicals are unsubstituted, partly or completely halogenated; R ^17a , R ^17b are each independently from one another selected from the group consisting of hydrogen and Ci-C4-alkyl.

In a particular group (1 a) of embodiments the variable R ⁴ is Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or may carry any combination of 1 , 2 or 3 radicals R ^5a , where R ^5a is as defined above and in particular selected from the group consisting of CN, N0 ₂ , Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy and S(0) _n NR ^17a R ^17b . In the particular group (1 a) of embodiments, the variable R ⁴ is in particular Ci-C6-alkyl, which carries any combination of 1 , 2 or 3 radicals R ^5a , where R ^5a is as defined above and in particular selected from the group consisting of CN, N0 ₂ , Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy and S(0) _n NR ^17a R ^17b and where Ci-C ₆ - alkyl may further carry 1 , 2 or 3 halogen atoms.

Examples of this type of radicals R ⁴ include the following radicals R-4.1 to R-4.12

R-4.1 trifluoromethyl,

R-4.2 difluorochloromethyl,

R-4.3 dichlorobromomethyl,

R-4.4 pentafluoroethyl,

R-4.5 2,2,2-trifluoroethyl,

R-4.6 1 -fluoroethenyl,

R-4.7 2,2-difluoroethenyl,

R-4.8 cyanomethyl,

R-4.9 1 -cyanoethyl,

R-4.10: nitromethyl;

R-4.1 1 : 1 -nitroethyl; and

R-4.12 difluoromethyl.

In the particular group (1 a) of embodiments, the variable R ⁴ is in particular Ci-C6-alkyl, which carries any combination of 1 , 2 or 3 radicals R ^5a , where R ^5a is as defined above and in particular selected from the group consisting of CN, NO2, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy and S(0) _n NR ^17a R ^17b and where Ci-C6-alkyl may further carry 1 , 2 or 3 halogen atoms.

In another particular group (1 b) of embodiments the variable R ⁴ is 6-membered heteroaryl, which is in particular selected from the group consisting of pyridinyl, pyrimidinyl, pyrazinyl and pyridazinyl, wherein 6-membered heteroaryl is unsubstituted or carries 1 , 2, 3 or 4 radicals R ¹⁰ , which are in particular selected from halogen, CN, NO2, Ci-C ₄ -alkyl, Ci-C ₄ -haloalkyl, C1-C4- alkoxy and Ci-C ₄ -haloalkoxy.

Examples of this type of radicals R ⁴ include 2-thiazolyl (R-40.1 ) and 2-pyrazinyl (R-40.2). In yet a further another particular group (1 c) of embodiments the variable R ⁴ is a radical of formula R-41 or R-42:

R-41 R-42 wherein # indicates the bond to the carbonyl group in formula (I)

A is CH ₂ , CH ₂ CH2 or CH2CH ₂ CH2,

Rioaa j _s hydrogen or a radical R ^10a as defined above, wherein R ^10aa is in particular selected from hydrogen, halogen, especially fluorine, S(0) _n R ^8a , CN and N0 ₂ , where n is 0, 1 or 2 and R ^8a is as defined above an in particular selected from Ci-C4-alkyl and Ci-

C4-haloalkyl.

Examples of radicals R-41 and R-42 include the following radicals R-41.1 to R-41 .20 and

R-42.1 to R-42.8:

R-41 .1 : cyclopropyl,

R-41 .2: cyclobutyl,

R-41.3: 1 -fluorocyclopropyl,

R-41.4: 1 -fluorocyclobutyl,

R-41.5: 1 -cyanocyclopropyl,

R-41.6: 1 -cyanocyclobutyl,

R-41.7: 1 -nitrocyclopropyl,

R-41.8: 1 -nitrocyclobutyl,

R-41.9: 1 -(methylthio)cyclopropyl,

R-41.10: 1 -(methylsulfinyl)cyclopropyl,

R-41.1 1 : 1 -(methylsulfonyl)cyclopropyl,

R-41.12: 1 -(ethylthio)cyclopropyl,

R-41.13: 1 -(ethylsulfinyl)cyclopropyl,

R-41.14: 1 -(ethylsulfonyl)cyclopropyl,

R-41.15: 1 -(methylthio)cyclobutyl,

R-41.16: 1-(methylsulfinyl)cyclobutyl,

R-41.17: 1 -(methylsulfonyl)cyclobutyl,

R-41.18: 1 -(ethylthio)cyclobutyl,

R-41.19: 1 -(ethylsulfinyl)cyclobutyl,

R-41.20: 1 -(ethylsulfonyl)cyclobutyl,

R-42.1 : 2-oxiranyl,

R-42.2: 2-oxetanyl,

R-42.3: 2-fluoro-2-oxiranyl,

R-42.4: 2-fluoro-2-oxetanyl,

R-42.5: 2-cyano-2-oxiranyl,

R-42.6: 2-cyano-2-oxetanyl,

R-42.7: 2-nitro-2-oxiranyl and

R-42.8: 2-nitro-2-oxetanyl.

In yet a further another particular group (1 d) of embodiments, the variable R ⁴ is a radicalmula R-43:

wherein n is 0, 1 or 2; and

R ^8a is as defined above and in particular Ci-C4-alkyl, such as methyl or ethyl, or Ci-C ₄ - haloalkyl such as trifluoromethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl or

pentafluoroethyl.

Examples of radicals R-43 are the radicals R-43.1 to R-43.2:

R-43.2: CF ₂ -S(0)-CH ₃ ,

R-43.3: CF ₂ -S(0) ₂ -CH ₃ ,

R-43.4: CF ₂ -S-C ₂ H ₅ ,

R-43.5: CF ₂ -S(0)-C ₂ H ₅

R-43.6: CF ₂ -S(0) ₂ -C ₂ H ₅ .

In yet a further another particular group (1 e) of embodiments, the variable R ⁴ is a radical of formula R-44:

wherein # indicates the bond to the carbonyl group in formula (I),

R ^x is hydrogen, halogen, CN , N0 ₂ , Ci-C ₄ -alkyl, Ci-C ₄ -haloalkyl, N R ^17a R ^17b or

S(0) ₂ N R ^7a R ^7b , S(0) ₂ R ^8a or C(=0)OR ⁸ and in particular hydrogen, CN , Ci-C ₄ -alkyl, such as methyl, or Ci-C ₄ -haloalkyl, such as trifluoromethyl;

R ¹⁶ is as defined above and in particular selected from the group consisting of C1-C6- alkyl and C ₂ -C6-alkenyl, where the two aforementioned radicals are unsubstituted, partly or completely halogenated and/or may carry 1 or 2 radicals R ⁷ , which are as defined above, and which are in particular selected from the group consisting of N0 ₂ , CN , OR ⁸ , S(0) _n R ^8a , N R ^17a R ^17b , C(=0)N R ^7a R ^7b , C(=0)OR ⁸ , C(=0)R ¹⁵ and N R ^7a -C(=0)R ^7a , or

R ¹⁶ is benzyl which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from

halogen, OH , CN , N0 ₂ , Ci-Ce-alkyI, d-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci- C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (C1-C6- alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl.

In formula R-44, R ¹⁶ is especially selected from the group consisting of Ci-C ₄ -alkyl, C1-C4- haloalkyl, where the two aforementioned radicals may carry 1 or 2 radicals R ⁷ , which are selected from the group consisting of NO2, CN and OR ⁸ , C2-C4-alkenyl, C2-C4-haloalkenyl, and benzyl which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, N0 ₂ , d-Ce-alkyl, Ci-C ₆ -haloalkyl, Ci-C ₆ -alkoxy, Ci-C ₆ haloalkoxy, Ci-C ₆ -alkylthio, Ci-C ₆ - haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl.

Examples of radicals R-44 are the radicals R-44.1 to R-44.40, where R ^x and R ¹⁶ are as defined in the rows of the following table A:

Table A: Radicals R-44

CH2-C ₆ H ₅ : benzyl

CH2-(4-CI-C ₆ H ₄ ): 4-chlorobenzyl

CH2-(4-(OCH ₃ )-C6H ₄ ): 4-methoxybenzyl In the context of groups (1 a), (1 b), (1 c), (1 d) and (1 e) of embodiments the variables R ^7a ,

R ⁸ , R ^8a , R ¹⁵ , R ^17a , R ^17b , irrespectively of their occurrence, have especially one of the following meanings:

R ^7a is selected from the group consisting of hydrogen, Ci-C ₄ -alkyl, Ci-C ₄ -haloalkyl, C3-

C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C ₄ -alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R ¹⁰ ;

R ⁸ is selected from the group consisting of Ci-C ₄ -alkyl, Ci-C ₄ -haloalkyl, C1-C4- alkylcarbonyl, Ci-C ₄ -haloalkylcarbonyl, Ci-C ₄ -alkoxycarbonyl,

NH2-C(0), Ci-C ₄ -alkylaminocarbonyl, di-(Ci-C ₄ -alkyl)aminocarbonyl, phenyl, benzyl, where the phenyl ring in the last five mentioned radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R ¹⁰ , phenylcarbonyl, phenoxycarbonyl, wherein the last two radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N0 ₂ , SCN, SF ₅ , OH, d-C ₆ -alkyl, C ₃ -C ₆ -cycloalkyl, Ci-C ₆ - haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci- C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl and phenylaminocarbonyl, wherein the last mentioned radical may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2, Ci-C6-alkyl, Ci- C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (C1-C6- alkoxy)carbonyl;

R ^8a is selected from the group consisting of Ci-C ₄ -alkyl, Ci-C ₄ -haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R ¹⁰ ; R ¹⁰ is selected from the group consisting of halogen, CN, OH, SH, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkylcarbonyl, C1-C4- haloalkylcarbonyl, Ci-C4-alkoxycarbonyl, NH2-C(0), Ci-C4-alkylthio, C1-C4- alkylsulfonyl, Ci-C4-haloalkylthio, Ci-C4-haloalkylsulfonyl, SO2NH2, C1-C4- alkylaminocarbony and di-(Ci-C4-alkyl)aminocarbonyl;

R ¹⁵ is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, NO2, d-Ce-alkyl, d-Ce-haloalkyl, d-Ce-alkoxy, Ci-Ce haloalkoxy, (Ci-C6-alkyl)carbonyl and (Ci-C6-alkoxy)carbonyl;

R ^17a , R ^17b are each independently from one another selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, phenyl and benzyl, where the phenyl ring in the last two substitutents is unsbustituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, N0 ₂ , Ci-C ₆ -alkyl, Ci-C ₆ -haloalkyl, Ci-C ₆ -alkoxy, Ci-C ₆ haloalkoxy, (Ci-C6-alkyl)carbonyl and (Ci-C6-alkoxy)carbonyl.

In the context of groups (1 a), (1 b), (1 c), (1 d) and (1 e) of embodiments the variables R ^7a R ⁸ , R ^8a , R ¹⁵ , R ^17a , R ^17b , irrespectively of their occurrence, have especially one of the following meanings:

R ^7a is selected from the group consisting of Ci-C4-alkyl or Ci-C4-haloalkyl;

R ⁸ is selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl;

R ^8a is selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl;

R ^9a is selected from the group consisting of hydrogen and Ci-C4-alkyl;

R ^9b is selected from the group consisting of hydrogen and Ci-C4-alkyl;

R ¹⁰ is selected from the group consisting of halogen, CN, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfonyl, C1-C4- haloalkylthio and Ci-C4-haloalkylsulfonyl;

R ¹⁵ is selected from the group consisting of hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl;

R ^16a is selected from the group consisting of Ci-C4-alkyl, which is unsubstituted, partly or completely halogenated;

R ^17a , R ^17b are each independently from one another selected from the group consisting of hydrogen and Ci-C4-alkyl.

In another particular group (2) of embodiments the variable R ⁴ is a radical 0-R ^5b or S-R ^5c , where R ^5b and R ^5c are as defined above. In this group (2) of embodiments, the variables R ^5b and R ^5c , independently of each other, are in particular selected from the group consisting of C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl-Ci-C4-alkyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated, and C3-C6- cycloalkyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , where R ¹⁰ is as defined above and in particular selected from the group consisting of halogen, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkyl and Ci-C4-haloalkyl. In this group (2) of embodiments, the variables R ^5b and R ^5c , independently of each other, are especially selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl and C3-C6-cycloa I kyl-C-i -C ₄ -a I kyl .

In yet another particular group (3) of embodiments the variable R ⁴ is a radical NR ^5d R ^5e , where R ^5d and R ^5e are as defined above. In this group (3) of embodiments, the variables R ^5d and R ^5e , independently of each other, have in particular the following meanings.

R ^5d is selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-

C6-cycloalkyl-Ci-C ₄ -alkyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated,

and C3-C6-cycloalkyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or

5 identical or different substituents R ¹⁰ , which is as defined above;

R ^5e is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl-Ci-C ₄ -alkyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated,

and C3-C6-cycloalkyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or

5 identical or different substituents R ¹⁰ , which is as defined above, or

R ^5d and R ^5e , if present, together may also form a bivalent radical, selected from the group

consisting of C2-C6-alkanediyl and C2-C6-alkenediyl, wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R ^7c , which is as defined above.

In this group (3) of embodiments, the variables R ^5d and R ^5e , independently of each other, have in especially the following meanings.

R ^5d is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl and C3-C6-cycloa I kyl-Ci -C ₄ -a I kyl ;

R ^5e is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-

C6-cycloalkyl and C3-C6-cycloalkyl-Ci-C ₄ -alkyl;

R ^5d and R ^5e , if present, together may also form a bivalent radical, selected from the group

consisting of C2-C6-alkanediyl, wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R ^7c , which is as defined above.

In the context of group (3) of embodiments the variables R ^7a , R ^7c and R ¹⁰ , are as defined above and irrespectively of their occurrence, have especially one of the following meanings: R ^7c is selected from the group consisting of hydrogen, Ci-C ₄ -alkyl, Ci-C ₄ -haloalkyl, C3-C6- cycloalkyl, C3-C6-cycloalkyl-Ci-C ₄ -alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R ¹⁰ ;

R ¹⁰ is selected from the group consisting of halogen, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, Ci- C ₄ -alkyl and Ci-C ₄ -haloalkyl.

In the compounds of formula I, and likewise in the compounds of the groups (1 ), (1 a), (1 b), (1 c), (1 d), (1 e), (2) and (3) of embodiments, the variable X is preferably O.

Particularly preferred are compounds of the formula (I) , in particular the compounds of groups (1 ), (1 a), (1 b), (1 c), (1 d), (1 e), (2) and (3) of embodiments, wherein Het is as defined above and in particular a radical Het-1 a, Het-1 1 a or Het-24, more particularly a radical Het-1 a, especially 6-chloropyridin-3-yl or 6-(trifluoromethyl)pyridin-3-yl;

X is preferably O;

R ¹ and R ² are independently from each other selected from the group consisting of

hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl or isopropyl, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl,

difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2- trifluoroethyl, or C3-C6-halocycloalkyl such as 1 -fluorocyclopropyl or 2,2- difluorocyclopropyl, or wherein R ¹ and R ² form, together with the carbon atom, which they attached to, a 3- to 5 membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl or cyclopentyl; and wherein R ¹ and R ² are more particularly independently from each other selected from the group consisting of hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl and especially where R ¹ and R ² are both hydrogen or R ¹ is methyl and R ² is hydrogen;

R ^3a is a C-bound radical, in particular

Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R ⁷ ,

- C3-C6-cycloalkyl, which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5

radicals R ¹⁰ , or

Cyc ¹ -Q ¹ , where

Cyc ¹ is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different

heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ,

Q ¹ is Ci-C ₄ -alkanediyl or C ₂ -C ₄ -alkenediyl, in particular CH ₂ , CH ₂ CH ₂ or CHCH ₃ ; and

R ^3b is a C-bound radical, in particular

Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R ⁷ ,

C3-C6-cycloalkyl, which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R ¹⁰ , or

- Cyc ² -Q ² , where

Cyc ² is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different

heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ ,

Q ² is Ci-C ₄ -alkanediyl or C ₂ -C ₄ -alkenediyl, in particular CH ₂ , CH ₂ CH ₂ or CHCH ₃ . Particularly preferred are also compounds of the formula (I), in particular the compounds of groups (1 ), (1 a), (1 b), (1 c), (1 d), (1 e), (2) and (3) of embodiments, wherein

Het is as defined above and in particular a radical Het-1 a, Het-1 1 a or Het-24, more particularly a radical Het-1 a, especially 6-chloropyridin-3-yl or 6-(trifluoromethyl)pyridin-3-yl;

X is preferably O;

R ¹ and R ² are independently from each other selected from the group consisting of

hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or C1-C3- haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl and especially where R ¹ and R ² are both hydrogen or R ¹ is methyl and R ² is hydrogen;

R ^3a is Ci-C6-alkyl, especially Ci-C3-alkyl, which is unsubstituted, partly or completely

halogenated and/or carries any combination of 1 , 2 or 3 radicals R ⁷ , or C3-C6-cycloalkyl, especially cyclopropyl, where C3-C6-cycloalkyl is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen and Ci-C4-alkyl. In this context, R ⁷ is as defined above and in particular from the group consisting of NO2, CN, C3-C6-cycloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, =N-0-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and R ⁷ is especially selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy; and

R ^3b is Ci-C6-alkyl or Ci-C6-haloalkyl, especially Ci-C3-alkyl or Ci-C3-haloalkyl, where alkyl and haloalkyl may carry 1 , 2 or 3 further radicals R ⁷ , which are identical or different. In this context, the radicals R ⁷ are as defined above and in particular from the group consisting of N0 ₂ , CN, Cs-Ce-cycloalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, =N-0-Ci-C ₄ -alkyl, C1-C4- alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and R ⁷ is especially selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy.

Particularly preferred are also compounds of the formula (I), in particular the compounds of groups (1 ), (1 a), (1 b), (1 c), (1 d), (1 e), (2) and (3) of embodiments, wherein

Het is as defined above and in particular a radical Het-1 a, Het-1 1 a or Het-24, more particularly a radical Het-1 a, especially 6-chloropyridin-3-yl or 6-(trifluoromethyl)pyridin-3-yl;

X is preferably O;

R ¹ and R ² are both hydrogen or R ¹ is methyl and R ² is hydrogen;

R ^3a is Ci-C3-alkyl, which is unsubstituted, partly or completely halogenated and/or carries a radical R ⁷ , or C3-C6-cycloalkyl, especially cyclopropyl, where R ⁷ is as defined above and in particular selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy and where

R ^3a is especially selected from the group consisting of methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropyl, cyclopropylmethyl,

CH ₂ CN, CH2CH2CN, CH2NO2 and CH2CH2NO2; is selected from the group consisting of Ci-C3-alkyl and Ci-C3-haloalkyl, especially from the group consisting of methyl, ethyl, difluoromethyl and trifluoromethyl. Apart from that, the variables R ⁶ , R ⁷ , R ^7a , R ^7c , R ^7d , R ⁸ , R ^8a , R ^9a , R ^9b , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ ,

R ¹⁵ , R ^16a , R ¹⁷ , R ^17a , R ^17b , R ^17c , irrespectively of their occurrence, in particular have the following meanings, if not stated otherwise:

R ⁶ irrespectively of its occurrence, is selected from the group consisting of halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluormethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as

difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.

R ⁷ irrespectively of its occurrence, is selected from the group consisting of CN, C1-C4- alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or

trifluormethoxy, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, C3- C6-cycloalkyl such as cyclopropyl, cyclobutyl or cyclopropyl, and C3-C6-halocycloalkyl.

R ^7a irrespectively of its occurrence, is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl- Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, C1-C4- haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1- difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1-difluoroethoxy, 2- fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.

R ^7c is preferably selected from the group consisting of halogen, Ci-C4-alkyl, C1-C4- haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, phenyl and benzyl, it being possible for phenyl and benzyl to be unsubstituted, partly or completely halogenated, or two radicals R ^7c bound the same carbon atom may be =CR ¹³ R ¹⁴ and where R ^7c is more particularly fluorine, Ci- C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, Ci-C4-haloalkyl, especially C1-C2- fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl or two radicals R ^7c bound the same carbon atom may be =CH ₂ .

R ⁸ irrespectively of its occurrence, is selected from the group consisting of C1-C4- alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl- Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci- C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n- propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy or 2,2,2-trifluoroethoxy.

R ^8a irrespectively of its occurrence, is selected from the group consisting of C1-C4- alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R ¹⁰ , which are preferably selected, independently of each other from halogen, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy and Ci-C4-haloalkyl.

R ^9a and R ^9b irrespectively of their occurrence, are preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or NR ^9a R ^9b may also be a saturated N-bound 3-, 4-, 5- or 6-membered heterocycle, which in addition to the nitrogen atom may have 1 further heteroatom as ring members, which is selected from O and N and where the N-bound 3-, 4-, 5- or 6-membered heterocycle may be unsubstituted or carry 1 , 2, 3 or 4 radicals selected from Ci-C4-alkyl and Ci-C4-haloalkyl. Examples of such radicals NR ^9a R ^9b include, but are not limited to methylamino, ethylamino, n-propylamino, isopropylamino, n- butylamino, 2-butylamino, isobutylamino, dimethylamino, diethylamino, di-n-propylamino, di-n- butylamino, N-methyl-N-ethylamino, N-methyl-N-propylamino, N-methyl-N-n-propylamino, N- methyl-N-isopropylamino, N-methyl-N-n-butylamino, N-methyl-N-2-butylamino, N-methyl-N- isobutylamino, 1 -pyrrolidinyl, 1 -piperidinyl, 1 -piperazinyl, 4-methyl-1 -piperazinyl and 4- morpholinyl.

R ¹⁰ irrespectively of its occurrence, is selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci- C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.

R ¹¹ , R ¹² independently of their occurrence, are selected from the group consisting of Ci- C6-alkyl, Ci-C6-alkoxy, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in last two radicals are unsubstituted or substituted with 1 , 2, or 3 identical or different radicals selected from fluorine, chlorine, Ci-C3-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy and Ci-C2-haloalkoxy.

R ¹³ , R ¹⁴ independently of their occurrence, are selected from the group consisting of hydrogen, fluorine, chlorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl or n-butyl, C3-C6- cycloalkyl, such as cyclopropyl, cyclobutyl or cyclopentyl, and phenyl. R ¹⁵ irrespectively of its occurrence, is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, C1-C4- haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.

R ^16a irrespectively of its occurrence, is selected from the group consisting of C1-C4- alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci- C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n- propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy or 2,2,2-trifluoroethoxy.

R ¹⁷ irrespectively of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C4-haloalkyl, Ci-C6-alkoxy, Ci-C4-haloalkoxy, C3-C6-alkenyl, C3-C6- cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n- propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2- trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and C1-C4- haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy,

trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.

R ^17a and R ^17b irrespectively of their occurrence, are preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or NR ^17a R ^17b may also be a saturated N-bound 3-, 4-, 5- or 6-membered heterocycle, which in addition to the nitrogen atom may have 1 further heteroatom as ring members, which is selected from O and N and where the N-bound 3-, 4-, 5- or 6-membered heterocycle may be unsubstituted or carry 1 , 2, 3 or 4 radicals selected from Ci-C4-alkyl and Ci-C4-haloalkyl. Examples of such radicals NR ^17a R ^17b include, but are not limited to methylamino, ethylamino, n-propylamino, isopropylamino, n- butylamino, 2-butylamino, isobutylamino, dimethylamino, diethylamino, di-n-propylamino, di-n- butylamino, N-methyl-N-ethylamino, N-methyl-N-propylamino, N-methyl-N-n-propylamino, N- methyl-N-isopropylamino, N-methyl-N-n-butylamino, N-methyl-N-2-butylamino, N-methyl-N- isobutylamino, 1 -pyrrolidinyl, 1 -piperidinyl, 1 -piperazinyl, 4-methyl-1 -piperazinyl and 4- morpholinyl.

R ^17c irrespectively of its occurrence, is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl- Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, C1-C4- haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.

Particular preference is given to the compounds of the formulae I-A.1 , I-A.2, I-A.3, I-A.4, I- A.5, I-A.6, I-A.7, I-A.8, to their tautomers, to their stereoisomers and to their salts, where R ¹ , R ^3a , R ^3b and R ⁴ are as defined above, in particular to those compounds, where

R ¹ is selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl or isopropyl, C3- C6-cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-C6-haloalkyl, in particular C1-C2- haloalkyi, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or C3-C6-halocycloalkyl such as 1 - fluorocyclopropyl or 2,2-difluorocyclopropyl,

in particular hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl and especially hydrogen or methyl,;

R ^3a is a C-bound radical, in particular

Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R ⁷ ,

C3-C6-cycloalkyl, which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R ¹⁰ , or

Cyc ¹ -Q ¹ , where

Cyc ¹ is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , Q ¹ is Ci-C ₄ -alkanediyl or C ₂ -C ₄ -alkenediyl, in particular CH ₂ , CH ₂ CH ₂ or CHCH ₃ ; R ^3b is a C-bound radical, in particular

Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R ⁷ , C3-C6-cycloalkyl, which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R ¹⁰ , or

Cyc ² -Q ² , where

Cyc ² is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different

heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R ¹⁰ , and

Q ² is Ci-C ₄ -alkanediyl or C ₂ -C ₄ -alkenediyl, in particular CH ₂ , CH ₂ CH ₂ or CHCH ₃ ;

R ⁴ is a radical R ^4a , in particular a radical R ⁴ as defined for the groups of embodiments (1 a), (1 b), (1 c), (1 d) or (1 e).

Particular preference is also given to the compounds of the formulae I-A.1 , I-A.2, I-A.3, I- A.4, I-A.5, I-A.6, I-A.7, I-A.8, to their tautomers, to their stereoisomers and to their salts, where R ¹ , R ^3a , R ^3b and R ⁴ are as defined below:

R ¹ is selected from the group consisting of hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl and especially hydrogen or methyl;

R ^3a is Ci-C6-alkyl, especially Ci-C3-alkyl, which is unsubstituted, partly or completely

halogenated and/or carries any combination of 1 , 2 or 3 radicals R ⁷ , or C3-C6-cycloalkyl, especially cyclopropyl, where C3-C6-cycloalkyl is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen and Ci-C ₄ -alkyl. In this context, R ⁷ is as defined above and in particular from the group consisting of N0 ₂ , CN, C3-C6-cycloalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ - haloalkoxy, =N-0-Ci-C ₄ -alkyl, Ci-C ₄ -alkylthio, Ci-C ₄ -alkylsulfinyl and Ci-C ₄ -alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and R ⁷ is especially selected from the group consisting of N0 ₂ , cyclopropyl, CN and Ci-C ₄ -alkoxy; R ^3b is Ci-C6-alkyl or Ci-C6-haloalkyl, especially Ci-C3-alkyl or Ci-C3-haloalkyl, where alkyl and haloalkyl may carry 1 , 2 or 3 further radicals R ⁷ , which are identical or different. In this context, the radicals R ⁷ are as defined above and in particular from the group consisting of N0 ₂ , CN, Cs-Ce-cycloalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -haloalkoxy, =N-0-Ci-C ₄ -alkyl, Ci-C ₄ - alkylthio, Ci-C ₄ -alkylsulfinyl and Ci-C ₄ -alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and R ⁷ is especially selected from the group consisting of N0 ₂ , cyclopropyl, CN and Ci-C ₄ -alkoxy, and

R ⁴ is a radical R ^4a , in particular a radical R ⁴ as defined for the groups of embodiments (1 a), (1 b), (1 c), (1 d) or (1 e).

Particular preference is also given to the compounds of the formulae I-A.1 , I-A.2, I-A.3, I-A.4, I-A.5, I-A.6, I-A.7, I-A.8, to their tautomers, to their stereoisomers and to their salts, where R ¹ , R ^3a , R ^3b and R ⁴ are as defined below: is hydrogen or methyl and especially hydrogen;

is Ci-C3-alkyl, which is unsubstituted, partly or completely halogenated and/or carries a radical R ⁷ , or C3-C6-cycloalkyl, especially cyclopropyl, where R ⁷ is as defined above and in particular selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy and where

R ^3a is especially selected from the group consisting of methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropyl, cyclopropylmethyl, CH2CN, CH2CH2CN, CH2NO2 and CH2CH2NO2; is selected from the group consisting of Ci-C3-alkyl and Ci-C3-haloalkyl, especially from the group consisting of methyl, ethyl, difluoromethyl and trifluoromethyl.

I-A.5 I-A.6

I-A.7 I-A.8

A special group of embodiments relates to the compounds of formula (I-A.1 ), to their tautomers, to their stereoisomers and to their salts, where R ¹ is hydrogen and where R ^3a , R ^3b and R ⁴ are as defined in lines 1 to 880 of the following table B (compounds I-A.1 a.1 to I-A.1 a.880). Further examples of this special group of embodiments are the compounds of formula (I-A.1 ), their tautomers, their stereoisomers and their salts, where R ¹ is CH3 and where R ^3a , R ^3b and R ⁴ have one of the meanings given in any of lines 1 to 880 of the following table B (compounds I-A.1 b.1 to I-A.1 b.880).

A further special group of embodiments relates to the compounds of formula (I-A.2), to their tautomers, to their stereoisomers and to their salts, where R ¹ is hydrogen and where R ^3a , R ^3b and R ⁴ are as defined in lines 1 to 880 of the following table B (compounds l-A.2a.1 to l-A.2a.880). Further examples of this special group of embodiments are the compounds of formula (I-A.2), their tautomers, their stereoisomers and their salts, where R ¹ is CH3 and where R ^3a , R ^3b and R ⁴ have one of the meanings given in any of lines 1 to 880 of the following table B (compounds l-A.2b.1 to l-A.2b.880).

A further special group of embodiments relates to the compounds of formula (I-A.3), to their tautomers, to their stereoisomers and to their salts, where R ¹ is hydrogen and where R ^3a , R ^3b and R ⁴ are as defined in lines 1 to 880 of the following table B (compounds l-A.3a.1 to l-A.3a.880). Further examples of this special group of embodiments are the compounds of formula (I-A.3), their tautomers, their stereoisomers and their salts, where R ¹ is CH3 and where R ^3a , R ^3b and R ⁴ have one of the meanings given in any of lines 1 to 880 of the following table B (compounds l-A.3b.1 to l-A.3b.880).

A further special group of embodiments relates to the compounds of formula (I-A.4), to their tautomers, to their stereoisomers and to their salts, where R ¹ is hydrogen and where R ^3a , R ^3b and R ⁴ are as defined in lines 1 to 880 of the following table B (compounds l-A.4a.1 to l-A.4a.880). Further examples of this special group of embodiments are the compounds of formula (I-A.4), their tautomers, their stereoisomers and their salts, where R ¹ is CH3 and where R ^3a , R ^3b and R ⁴ have one of the meanings given in any of lines 1 to 880 of the following table B (compounds l-A.4b.1 to l-A.4b.880).

A special group of embodiments relates to the compounds of formula (I-A.5), to their tautomers, to their stereoisomers and to their salts, where R ¹ is hydrogen and where R ^3a , R ^3b and R ⁴ are as defined in lines 1 to 880 of the following table B (compounds l-A.5a.1 to l-A.5a.880). Further examples of this special group of embodiments are the compounds of formula (I-A.5), their tautomers, their stereoisomers and their salts, where R ¹ is CH3 and where R ^3a , R ^3b and R ⁴ have one of the meanings given in any of lines 1 to 880 of the following table B (compounds I-A.5 to l-A.5b.880).

A further special group of embodiments relates to the compounds of formula (I-A.6), to their tautomers, to their stereoisomers and to their salts, where R ¹ is hydrogen and where R ^3a , R ^3b and R ⁴ are as defined in lines 1 to 880 of the following table B (compounds l-A.6a.1 to l-A.6a.880). Further examples of this special group of embodiments are the compounds of formula (I-A.6), their tautomers, their stereoisomers and their salts, where R ¹ is CH3 and where R ^3a , R ^3b and R ⁴ have one of the meanings given in any of lines 1 to 880 of the following table B (compounds l-A.6b.1 to l-A.6b.880).

A further special group of embodiments relates to the compounds of formula (I-A.7), to their tautomers, to their stereoisomers and to their salts, where R ¹ is hydrogen and where R ^3a , R ^3b and R ⁴ are as defined in lines 1 to 880 of the following table B (compounds l-A.7a.1 to l-A.7a.880). Further examples of this special group of embodiments are the compounds of formula (I-A.7), their tautomers, their stereoisomers and their salts, where R ¹ is CH3 and where R ^3a , R ^3b and R ⁴ have one of the meanings given in any of lines 1 to 880 of the following table B (compounds l-A.7b.1 to l-A.7b.880).

A further special group of embodiments relates to the compounds of formula (I-A.8), to their tautomers, to their stereoisomers and to their salts, where R ¹ is hydrogen and where R ^3a , R ^3b and R ⁴ are as defined in lines 1 to 880 of the following table B (compounds l-A.8a.1 to l-A.8a.880). Further examples of this special group of embodiments are the compounds of formula (I-A.8), their tautomers, their stereoisomers and their salts, where R ¹ is CH3 and where R ^3a , R ^3b and R ⁴ have one of the meanings given in any of lines 1 to 880 of the following table B (compounds l-A.8b.1 to l-A.8b.880).

Table B: _R 3a _R 3b R ⁴

_R 3a _R 3b R ⁴ 14 CHs CHs R-40.2

1 CH ₃ CH ₃ R-4.1 15 CHs CHs R-41 .1

2 CH ₃ CH ₃ R-4.2 16 CHs CHs R-41 .2

3 CH ₃ CH ₃ R-4.3 17 CHs CHs R-41 .3

4 CH ₃ CH ₃ R-4.4 18 CHs CHs R-41 .4

5 CH ₃ CH ₃ R-4.5 19 CHs CHs R-41 .5

6 CH ₃ CH ₃ R-4.6 20 CHs CHs R-41 .6

7 CH ₃ CH ₃ R-4.7 21 CHs CHs R-41 .7

8 CH ₃ CH ₃ R-4.8 22 CHs CHs R-41 .8

9 CH ₃ CH ₃ R-4.9 23 CHs CHs R-41 .9

10 CH ₃ CH ₃ R-4.10 24 CHs CHs R-41 .10

1 1 CH ₃ CH ₃ R-4.1 1 25 CHs CHs R-41.1 1

12 CH ₃ CH ₃ R-4.12 26 CHs CHs R-41.12

13 CH ₃ CH ₃ R-40.1 27 CHs CHs R-41 .13 _R 3a _R 3b R ⁴ _R 3a _R 3b R ⁴

CHs CHs R-41 .14 66 CHs CHs R-44.18

CHs CHs R-41 .15 67 CHs CHs R-44.19

CHs CHs R-41 .16 68 CHs CHs R-44.20

CHs CHs R-41 .17 69 CHs CHs R-44.21

CHs CHs R-41 .18 70 CHs CHs R-44.22

CHs CHs R-41 .19 71 CHs CHs R-44.23

CHs CHs R-41 .20 72 CHs CHs R-44.24

CHs CHs R-42.1 73 CHs CHs R-44.25

CHs CHs R-42.2 74 CHs CHs R-44.26

CHs CHs R-42.3 75 CHs CHs R-44.27

CHs CHs R-42.4 76 CHs CHs R-44.28

CHs CHs R-42.5 77 CHs CHs R-44.29

CHs CHs R-42.6 78 CHs CHs R-44.30

CHs CHs R-42.7 79 CHs CHs R-44.31

CHs CHs R-42.8 80 CHs CHs R-44.32

CHs CHs R-43.1 81 CHs CHs R-44.33

CHs CHs R-43.2 82 CHs CHs R-44.34

CHs CHs R-43.3 83 CHs CHs R-44.35

CHs CHs R-43.4 84 CHs CHs R-44.36

CHs CHs R-43.5 85 CHs CHs R-44.37

CHs CHs R-43.6 86 CHs CHs R-44.38

CHs CHs R-44.1 87 CHs CHs R-44.39

CHs CHs R-44.2 88 CHs CHs R-44.40

CHs CHs R-44.3 89 CHs CFs R-4.1

CHs CHs R-44.4 90 CHs CFs R-4.2

CHs CHs R-44.5 91 CHs CFs R-4.3

CHs CHs R-44.6 92 CHs CFs R-4.4

CHs CHs R-44.7 93 CHs CFs R-4.5

CHs CHs R-44.8 94 CHs CFs R-4.6

CHs CHs R-44.9 95 CHs CFs R-4.7

CHs CHs R-44.10 96 CHs CFs R-4.8

CHs CHs R-44.1 1 97 CHs CFs R-4.9

CHs CHs R-44.12 98 CHs CFs R-4.10

CHs CHs R-44.13 99 CHs CFs R-4.1 1

CHs CHs R-44.14 100 CHs CFs R-4.12

CHs CHs R-44.15 101 CHs CFs R-40.1

CHs CHs R-44.16 102 CHs CFs R-40.2

CHs CHs R-44.17 103 CHs CFs R-41 .1 _R 3a _R 3b R ⁴ _R 3a _R 3b R ⁴

104 CHs CFs R-41 .2 142 CHs CFs R-44.6

105 CHs CFs R-41 .3 143 CHs CFs R-44.7

106 CHs CFs R-41 .4 144 CHs CFs R-44.8

107 CHs CFs R-41 .5 145 CHs CFs R-44.9

108 CHs CFs R-41 .6 146 CHs CFs R-44.10

109 CHs CFs R-41 .7 147 CHs CFs R-44.1 1

1 10 CHs CFs R-41 .8 148 CHs CFs R-44.12

1 1 1 CHs CFs R-41 .9 149 CHs CFs R-44.13

1 12 CHs CFs R-41 .10 150 CHs CFs R-44.14

1 13 CHs CFs R-41.1 1 151 CHs CFs R-44.15

1 14 CHs CFs R-41.12 152 CHs CFs R-44.16

1 15 CHs CFs R-41 .13 153 CHs CFs R-44.17

1 16 CHs CFs R-41 .14 154 CHs CFs R-44.18

1 17 CHs CFs R-41 .15 155 CHs CFs R-44.19

1 18 CHs CFs R-41 .16 156 CHs CFs R-44.20

1 19 CHs CFs R-41 .17 157 CHs CFs R-44.21

120 CHs CFs R-41 .18 158 CHs CFs R-44.22

121 CHs CFs R-41 .19 159 CHs CFs R-44.23

122 CHs CFs R-41 .20 160 CHs CFs R-44.24

123 CHs CFs R-42.1 161 CHs CFs R-44.25

124 CHs CFs R-42.2 162 CHs CFs R-44.26

125 CHs CFs R-42.3 163 CHs CFs R-44.27

126 CHs CFs R-42.4 164 CHs CFs R-44.28

127 CHs CFs R-42.5 165 CHs CFs R-44.29

128 CHs CFs R-42.6 166 CHs CFs R-44.30

129 CHs CFs R-42.7 167 CHs CFs R-44.31

130 CHs CFs R-42.8 168 CHs CFs R-44.32

131 CHs CFs R-43.1 169 CHs CFs R-44.33

132 CHs CFs R-43.2 170 CHs CFs R-44.34

133 CHs CFs R-43.3 171 CHs CFs R-44.35

134 CHs CFs R-43.4 172 CHs CFs R-44.36

135 CHs CFs R-43.5 173 CHs CFs R-44.37

136 CHs CFs R-43.6 174 CHs CFs R-44.38

137 CHs CFs R-44.1 175 CHs CFs R-44.39

138 CHs CFs R-44.2 176 CHs CFs R-44.40

139 CHs CFs R-44.3 177 CH2CF3 CHs R-4.1

140 CHs CFs R-44.4 178 CH2CF3 CHs R-4.2

141 CHs CFs R-44.5 179 CH2CF3 CHs R-4.3 _R 3a _R 3b R ⁴ _R 3a _R 3b R ⁴

180 CH2CF3 CH ₃ R-4.4 218 CH2CF3 CHs R-42.8

181 CH2CF3 CH ₃ R-4.5 219 CH2CF3 CHs R-43.1

182 CH2CF3 CH ₃ R-4.6 220 CH2CF3 CHs R-43.2

183 CH2CF3 CH ₃ R-4.7 221 CH2CF3 CHs R-43.3

184 CH2CF3 CH ₃ R-4.8 222 CH2CF3 CHs R-43.4

185 CH2CF3 CH ₃ R-4.9 223 CH2CF3 CHs R-43.5

186 CH2CF3 CH ₃ R-4.10 224 CH2CF3 CHs R-43.6

187 CH2CF3 CH ₃ R-4.1 1 225 CH2CF3 CHs R-44.1

188 CH2CF3 CH ₃ R-4.12 226 CH2CF3 CHs R-44.2

189 CH2CF3 CH ₃ R-40.1 227 CH2CF3 CHs R-44.3

190 CH2CF3 CH ₃ R-40.2 228 CH2CF3 CHs R-44.4

191 CH2CF3 CH ₃ R-41 .1 229 CH2CF3 CHs R-44.5

192 CH2CF3 CH ₃ R-41 .2 230 CH2CF3 CHs R-44.6

193 CH2CF3 CH ₃ R-41 .3 231 CH2CF3 CHs R-44.7

194 CH2CF3 CH ₃ R-41 .4 232 CH2CF3 CHs R-44.8

195 CH2CF3 CH ₃ R-41 .5 233 CH2CF3 CHs R-44.9

196 CH2CF3 CH ₃ R-41 .6 234 CH2CF3 CHs R-44.10

197 CH2CF3 CH ₃ R-41 .7 235 CH2CF3 CHs R-44.1 1

198 CH2CF3 CH ₃ R-41 .8 236 CH2CF3 CHs R-44.12

199 CH2CF3 CH ₃ R-41 .9 237 CH2CF3 CHs R-44.13

200 CH2CF3 CH ₃ R-41 .10 238 CH2CF3 CHs R-44.14

201 CH2CF3 CH ₃ R-41.1 1 239 CH2CF3 CHs R-44.15

202 CH2CF3 CH ₃ R-41.12 240 CH2CF3 CHs R-44.16

203 CH2CF3 CH ₃ R-41 .13 241 CH2CF3 CHs R-44.17

204 CH2CF3 CH ₃ R-41 .14 242 CH2CF3 CHs R-44.18

205 CH2CF3 CH ₃ R-41 .15 243 CH2CF3 CHs R-44.19

206 CH2CF3 CH ₃ R-41 .16 244 CH2CF3 CHs R-44.20

207 CH2CF3 CH ₃ R-41 .17 245 CH2CF3 CHs R-44.21

208 CH2CF3 CH ₃ R-41 .18 246 CH2CF3 CHs R-44.22

209 CH2CF3 CH ₃ R-41 .19 247 CH2CF3 CHs R-44.23

210 CH2CF3 CH ₃ R-41 .20 248 CH2CF3 CHs R-44.24

21 1 CH2CF3 CH ₃ R-42.1 249 CH2CF3 CHs R-44.25

212 CH2CF3 CH ₃ R-42.2 250 CH2CF3 CHs R-44.26

213 CH2CF3 CH ₃ R-42.3 251 CH2CF3 CHs R-44.27

214 CH2CF3 CH ₃ R-42.4 252 CH2CF3 CHs R-44.28

215 CH2CF3 CH ₃ R-42.5 253 CH2CF3 CHs R-44.29

216 CH2CF3 CH ₃ R-42.6 254 CH2CF3 CHs R-44.30

217 CH2CF3 CH ₃ R-42.7 255 CH2CF3 CHs R-44.31 _R 3a _R 3b R ⁴ _R 3a _R 3b R ⁴

256 CH2CF3 CH ₃ R-44.32 294 CH2CF3 CF ₃ R-41 .16

257 CH2CF3 CH ₃ R-44.33 295 CH2CF3 CF ₃ R-41 .17

258 CH2CF3 CH ₃ R-44.34 296 CH2CF3 CF ₃ R-41 .18

259 CH2CF3 CH ₃ R-44.35 297 CH2CF3 CF ₃ R-41 .19

260 CH2CF3 CH ₃ R-44.36 298 CH2CF3 CF ₃ R-41 .20

261 CH2CF3 CH ₃ R-44.37 299 CH2CF3 CF ₃ R-42.1

262 CH2CF3 CH ₃ R-44.38 300 CH2CF3 CF ₃ R-42.2

263 CH2CF3 CH ₃ R-44.39 301 CH2CF3 CF ₃ R-42.3

264 CH2CF3 CH ₃ R-44.40 302 CH2CF3 CF ₃ R-42.4

265 CH2CF3 CF ₃ R-4.1 303 CH2CF3 CF ₃ R-42.5

266 CH2CF3 CF ₃ R-4.2 304 CH2CF3 CF ₃ R-42.6

267 CH2CF3 CF ₃ R-4.3 305 CH2CF3 CF ₃ R-42.7

268 CH2CF3 CF ₃ R-4.4 306 CH2CF3 CF ₃ R-42.8

269 CH2CF3 CF ₃ R-4.5 307 CH2CF3 CF ₃ R-43.1

270 CH2CF3 CF ₃ R-4.6 308 CH2CF3 CF ₃ R-43.2

271 CH2CF3 CF ₃ R-4.7 309 CH2CF3 CF ₃ R-43.3

272 CH2CF3 CF ₃ R-4.8 310 CH2CF3 CF ₃ R-43.4

273 CH2CF3 CF ₃ R-4.9 31 1 CH2CF3 CF ₃ R-43.5

274 CH2CF3 CF ₃ R-4.10 312 CH2CF3 CF ₃ R-43.6

275 CH2CF3 CF ₃ R-4.1 1 313 CH2CF3 CF ₃ R-44.1

276 CH2CF3 CF ₃ R-4.12 314 CH2CF3 CF ₃ R-44.2

277 CH2CF3 CF ₃ R-40.1 315 CH2CF3 CF ₃ R-44.3

278 CH2CF3 CF ₃ R-40.2 316 CH2CF3 CF ₃ R-44.4

279 CH2CF3 CF ₃ R-41 .1 317 CH2CF3 CF ₃ R-44.5

280 CH2CF3 CF ₃ R-41 .2 318 CH2CF3 CF ₃ R-44.6

281 CH2CF3 CF ₃ R-41 .3 319 CH2CF3 CF ₃ R-44.7

282 CH2CF3 CF ₃ R-41 .4 320 CH2CF3 CF ₃ R-44.8

283 CH2CF3 CF ₃ R-41 .5 321 CH2CF3 CF ₃ R-44.9

284 CH2CF3 CF ₃ R-41 .6 322 CH2CF3 CF ₃ R-44.10

285 CH2CF3 CF ₃ R-41 .7 323 CH2CF3 CF ₃ R-44.1 1

286 CH2CF3 CF ₃ R-41 .8 324 CH2CF3 CF ₃ R-44.12

287 CH2CF3 CF ₃ R-41 .9 325 CH2CF3 CF ₃ R-44.13

288 CH2CF3 CF ₃ R-41 .10 326 CH2CF3 CF ₃ R-44.14

289 CH2CF3 CF ₃ R-41.1 1 327 CH2CF3 CF ₃ R-44.15

290 CH2CF3 CF ₃ R-41.12 328 CH2CF3 CF ₃ R-44.16

291 CH2CF3 CF ₃ R-41 .13 329 CH2CF3 CF ₃ R-44.17

292 CH2CF3 CF ₃ R-41 .14 330 CH2CF3 CF ₃ R-44.18

293 CH2CF3 CF ₃ R-41 .15 331 CH2CF3 CF ₃ R-44.19 _R 3a _R 3b R ⁴ _R 3a _R 3b R ⁴

332 CH2CF3 CF ₃ R-44.20 370 CH2CHF2 CH ₃ R-41 .4

333 CH2CF3 CF ₃ R-44.21 371 CH2CHF2 CH ₃ R-41 .5

334 CH2CF3 CF ₃ R-44.22 372 CH2CHF2 CH ₃ R-41 .6

335 CH2CF3 CF ₃ R-44.23 373 CH2CHF2 CH ₃ R-41 .7

336 CH2CF3 CF ₃ R-44.24 374 CH2CHF2 CH ₃ R-41 .8

337 CH2CF3 CF ₃ R-44.25 375 CH2CHF2 CH ₃ R-41 .9

338 CH2CF3 CF ₃ R-44.26 376 CH2CHF2 CH ₃ R-41 .10

339 CH2CF3 CF ₃ R-44.27 377 CH2CHF2 CH ₃ R-41.1 1

340 CH2CF3 CF ₃ R-44.28 378 CH2CHF2 CH ₃ R-41.12

341 CH2CF3 CF ₃ R-44.29 379 CH2CHF2 CH ₃ R-41 .13

342 CH2CF3 CF ₃ R-44.30 380 CH2CHF2 CH ₃ R-41 .14

343 CH2CF3 CF ₃ R-44.31 381 CH2CHF2 CH ₃ R-41 .15

344 CH2CF3 CF ₃ R-44.32 382 CH2CHF2 CH ₃ R-41 .16

345 CH2CF3 CF ₃ R-44.33 383 CH2CHF2 CH ₃ R-41 .17

346 CH2CF3 CF ₃ R-44.34 384 CH2CHF2 CH ₃ R-41 .18

347 CH2CF3 CF ₃ R-44.35 385 CH2CHF2 CH ₃ R-41 .19

348 CH2CF3 CF ₃ R-44.36 386 CH2CHF2 CH ₃ R-41 .20

349 CH2CF3 CF ₃ R-44.37 387 CH2CHF2 CH ₃ R-42.1

350 CH2CF3 CF ₃ R-44.38 388 CH2CHF2 CH ₃ R-42.2

351 CH2CF3 CF ₃ R-44.39 389 CH2CHF2 CH ₃ R-42.3

352 CH2CF3 CF ₃ R-44.40 390 CH2CHF2 CH ₃ R-42.4

353 CH2CHF2 CH ₃ R-4.1 391 CH2CHF2 CH ₃ R-42.5

354 CH2CHF2 CH ₃ R-4.2 392 CH2CHF2 CH ₃ R-42.6

355 CH2CHF2 CH ₃ R-4.3 393 CH2CHF2 CH ₃ R-42.7

356 CH2CHF2 CH ₃ R-4.4 394 CH2CHF2 CH ₃ R-42.8

357 CH2CHF2 CH ₃ R-4.5 395 CH2CHF2 CH ₃ R-43.1

358 CH2CHF2 CH ₃ R-4.6 396 CH2CHF2 CH ₃ R-43.2

359 CH2CHF2 CH ₃ R-4.7 397 CH2CHF2 CH ₃ R-43.3

360 CH2CHF2 CH ₃ R-4.8 398 CH2CHF2 CH ₃ R-43.4

361 CH2CHF2 CH ₃ R-4.9 399 CH2CHF2 CH ₃ R-43.5

362 CH2CHF2 CH ₃ R-4.10 400 CH2CHF2 CH ₃ R-43.6

363 CH2CHF2 CH ₃ R-4.1 1 401 CH2CHF2 CH ₃ R-44.1

364 CH2CHF2 CH ₃ R-4.12 402 CH2CHF2 CH ₃ R-44.2

365 CH2CHF2 CH ₃ R-40.1 403 CH2CHF2 CH ₃ R-44.3

366 CH2CHF2 CH ₃ R-40.2 404 CH2CHF2 CH ₃ R-44.4

367 CH2CHF2 CH ₃ R-41 .1 405 CH2CHF2 CH ₃ R-44.5

368 CH2CHF2 CH ₃ R-41 .2 406 CH2CHF2 CH ₃ R-44.6

369 CH2CHF2 CH ₃ R-41 .3 407 CH2CHF2 CH ₃ R-44.7 _R 3a _R 3b R ⁴ _R 3a _R 3b R ⁴

408 CH2CHF2 CHs R-44.8 446 CH2CHF2 CFs R-4.6

409 CH2CHF2 CHs R-44.9 447 CH2CHF2 CFs R-4.7

410 CH2CHF2 CHs R-44.10 448 CH2CHF2 CFs R-4.8

41 1 CH2CHF2 CHs R-44.1 1 449 CH2CHF2 CFs R-4.9

412 CH2CHF2 CHs R-44.12 450 CH2CHF2 CFs R-4.10

413 CH2CHF2 CHs R-44.13 451 CH2CHF2 CFs R-4.1 1

414 CH2CHF2 CHs R-44.14 452 CH2CHF2 CFs R-4.12

415 CH2CHF2 CHs R-44.15 453 CH2CHF2 CFs R-40.1

416 CH2CHF2 CHs R-44.16 454 CH2CHF2 CFs R-40.2

417 CH2CHF2 CHs R-44.17 455 CH2CHF2 CFs R-41 .1

418 CH2CHF2 CHs R-44.18 456 CH2CHF2 CFs R-41 .2

419 CH2CHF2 CHs R-44.19 457 CH2CHF2 CFs R-41 .3

420 CH2CHF2 CHs R-44.20 458 CH2CHF2 CFs R-41 .4

421 CH2CHF2 CHs R-44.21 459 CH2CHF2 CFs R-41 .5

422 CH2CHF2 CHs R-44.22 460 CH2CHF2 CFs R-41 .6

423 CH2CHF2 CHs R-44.23 461 CH2CHF2 CFs R-41 .7

424 CH2CHF2 CHs R-44.24 462 CH2CHF2 CFs R-41 .8

425 CH2CHF2 CHs R-44.25 463 CH2CHF2 CFs R-41 .9

426 CH2CHF2 CHs R-44.26 464 CH2CHF2 CFs R-41 .10

427 CH2CHF2 CHs R-44.27 465 CH2CHF2 CFs R-41.1 1

428 CH2CHF2 CHs R-44.28 466 CH2CHF2 CFs R-41.12

429 CH2CHF2 CHs R-44.29 467 CH2CHF2 CFs R-41 .13

430 CH2CHF2 CHs R-44.30 468 CH2CHF2 CFs R-41 .14

431 CH2CHF2 CHs R-44.31 469 CH2CHF2 CFs R-41 .15

432 CH2CHF2 CHs R-44.32 470 CH2CHF2 CFs R-41 .16

433 CH2CHF2 CHs R-44.33 471 CH2CHF2 CFs R-41 .17

434 CH2CHF2 CHs R-44.34 472 CH2CHF2 CFs R-41 .18

435 CH2CHF2 CHs R-44.35 473 CH2CHF2 CFs R-41 .19

436 CH2CHF2 CHs R-44.36 474 CH2CHF2 CFs R-41 .20

437 CH2CHF2 CHs R-44.37 475 CH2CHF2 CFs R-42.1

438 CH2CHF2 CHs R-44.38 476 CH2CHF2 CFs R-42.2

439 CH2CHF2 CHs R-44.39 477 CH2CHF2 CFs R-42.3

440 CH2CHF2 CHs R-44.40 478 CH2CHF2 CFs R-42.4

441 CH2CHF2 CFs R-4.1 479 CH2CHF2 CFs R-42.5

442 CH2CHF2 CFs R-4.2 480 CH2CHF2 CFs R-42.6

443 CH2CHF2 CFs R-4.3 481 CH2CHF2 CFs R-42.7

444 CH2CHF2 CFs R-4.4 482 CH2CHF2 CFs R-42.8

445 CH2CHF2 CFs R-4.5 483 CH2CHF2 CFs R-43.1 _R 3a _R 3b R ⁴ _R 3a _R 3b R ⁴

484 CH2CHF2 CFs R-43.2 522 CH2CHF2 CFs R-44.34

485 CH2CHF2 CFs R-43.3 523 CH2CHF2 CFs R-44.35

486 CH2CHF2 CFs R-43.4 524 CH2CHF2 CFs R-44.36

487 CH2CHF2 CFs R-43.5 525 CH2CHF2 CFs R-44.37

488 CH2CHF2 CFs R-43.6 526 CH2CHF2 CFs R-44.38

489 CH2CHF2 CFs R-44.1 527 CH2CHF2 CFs R-44.39

490 CH2CHF2 CFs R-44.2 528 CH2CHF2 CFs R-44.40

491 CH2CHF2 CFs R-44.3 529 CH ₂ CN CHs R-4.1

492 CH2CHF2 CFs R-44.4 530 CH ₂ CN CHs R-4.2

493 CH2CHF2 CFs R-44.5 531 CH ₂ CN CHs R-4.3

494 CH2CHF2 CFs R-44.6 532 CH ₂ CN CHs R-4.4

495 CH2CHF2 CFs R-44.7 533 CH ₂ CN CHs R-4.5

496 CH2CHF2 CFs R-44.8 534 CH ₂ CN CHs R-4.6

497 CH2CHF2 CFs R-44.9 535 CH ₂ CN CHs R-4.7

498 CH2CHF2 CFs R-44.10 536 CH ₂ CN CHs R-4.8

499 CH2CHF2 CFs R-44.1 1 537 CH ₂ CN CHs R-4.9

500 CH2CHF2 CFs R-44.12 538 CH ₂ CN CHs R-4.10

501 CH2CHF2 CFs R-44.13 539 CH ₂ CN CHs R-4.1 1

502 CH2CHF2 CFs R-44.14 540 CH ₂ CN CHs R-4.12

503 CH2CHF2 CFs R-44.15 541 CH ₂ CN CHs R-40.1

504 CH2CHF2 CFs R-44.16 542 CH ₂ CN CHs R-40.2

505 CH2CHF2 CFs R-44.17 543 CH ₂ CN CHs R-41 .1

506 CH2CHF2 CFs R-44.18 544 CH ₂ CN CHs R-41 .2

507 CH2CHF2 CFs R-44.19 545 CH ₂ CN CHs R-41 .3

508 CH2CHF2 CFs R-44.20 546 CH ₂ CN CHs R-41 .4

509 CH2CHF2 CFs R-44.21 547 CH ₂ CN CHs R-41 .5

510 CH2CHF2 CFs R-44.22 548 CH ₂ CN CHs R-41 .6

51 1 CH2CHF2 CFs R-44.23 549 CH ₂ CN CHs R-41 .7

512 CH2CHF2 CFs R-44.24 550 CH ₂ CN CHs R-41 .8

513 CH2CHF2 CFs R-44.25 551 CH ₂ CN CHs R-41 .9

514 CH2CHF2 CFs R-44.26 552 CH ₂ CN CHs R-41 .10

515 CH2CHF2 CFs R-44.27 553 CH ₂ CN CHs R-41.1 1

516 CH2CHF2 CFs R-44.28 554 CH ₂ CN CHs R-41.12

517 CH2CHF2 CFs R-44.29 555 CH ₂ CN CHs R-41 .13

518 CH2CHF2 CFs R-44.30 556 CH ₂ CN CHs R-41 .14

519 CH2CHF2 CFs R-44.31 557 CH ₂ CN CHs R-41 .15

520 CH2CHF2 CFs R-44.32 558 CH ₂ CN CHs R-41 .16

521 CH2CHF2 CFs R-44.33 559 CH ₂ CN CHs R-41 .17 _R 3a _R 3b R ⁴ _R 3a _R 3b R ⁴

560 CH ₂ CN CHs R-41 .18 598 CH ₂ CN CHs R-44.22

561 CH ₂ CN CHs R-41 .19 599 CH ₂ CN CHs R-44.23

562 CH ₂ CN CHs R-41 .20 600 CH ₂ CN CHs R-44.24

563 CH ₂ CN CHs R-42.1 601 CH ₂ CN CHs R-44.25

564 CH ₂ CN CHs R-42.2 602 CH ₂ CN CHs R-44.26

565 CH ₂ CN CHs R-42.3 603 CH ₂ CN CHs R-44.27

566 CH ₂ CN CHs R-42.4 604 CH ₂ CN CHs R-44.28

567 CH ₂ CN CHs R-42.5 605 CH ₂ CN CHs R-44.29

568 CH ₂ CN CHs R-42.6 606 CH ₂ CN CHs R-44.30

569 CH ₂ CN CHs R-42.7 607 CH ₂ CN CHs R-44.31

570 CH ₂ CN CHs R-42.8 608 CH ₂ CN CHs R-44.32

571 CH ₂ CN CHs R-43.1 609 CH ₂ CN CHs R-44.33

572 CH ₂ CN CHs R-43.2 610 CH ₂ CN CHs R-44.34

573 CH ₂ CN CHs R-43.3 61 1 CH ₂ CN CHs R-44.35

574 CH ₂ CN CHs R-43.4 612 CH ₂ CN CHs R-44.36

575 CH ₂ CN CHs R-43.5 613 CH ₂ CN CHs R-44.37

576 CH ₂ CN CHs R-43.6 614 CH ₂ CN CHs R-44.38

577 CH ₂ CN CHs R-44.1 615 CH ₂ CN CHs R-44.39

578 CH ₂ CN CHs R-44.2 616 CH ₂ CN CHs R-44.40

579 CH ₂ CN CHs R-44.3 617 CH ₂ CN CFs R-4.1

580 CH ₂ CN CHs R-44.4 618 CH ₂ CN CFs R-4.2

581 CH ₂ CN CHs R-44.5 619 CH ₂ CN CFs R-4.3

582 CH ₂ CN CHs R-44.6 620 CH ₂ CN CFs R-4.4

583 CH ₂ CN CHs R-44.7 621 CH ₂ CN CFs R-4.5

584 CH ₂ CN CHs R-44.8 622 CH ₂ CN CFs R-4.6

585 CH ₂ CN CHs R-44.9 623 CH ₂ CN CFs R-4.7

586 CH ₂ CN CHs R-44.10 624 CH ₂ CN CFs R-4.8

587 CH ₂ CN CHs R-44.1 1 625 CH ₂ CN CFs R-4.9

588 CH ₂ CN CHs R-44.12 626 CH ₂ CN CFs R-4.10

589 CH ₂ CN CHs R-44.13 627 CH ₂ CN CFs R-4.1 1

590 CH ₂ CN CHs R-44.14 628 CH ₂ CN CFs R-4.12

591 CH ₂ CN CHs R-44.15 629 CH ₂ CN CFs R-40.1

592 CH ₂ CN CHs R-44.16 630 CH ₂ CN CFs R-40.2

593 CH ₂ CN CHs R-44.17 631 CH ₂ CN CFs R-41 .1

594 CH ₂ CN CHs R-44.18 632 CH ₂ CN CFs R-41 .2

595 CH ₂ CN CHs R-44.19 633 CH ₂ CN CFs R-41 .3

596 CH ₂ CN CHs R-44.20 634 CH ₂ CN CFs R-41 .4

597 CH ₂ CN CHs R-44.21 635 CH ₂ CN CFs R-41 .5 _R 3a _R 3b R ⁴ _R 3a _R 3b R ⁴

636 CH ₂ CN CFs R-41 .6 674 CH ₂ CN CFs R-44.10

637 CH ₂ CN CFs R-41 .7 675 CH ₂ CN CFs R-44.1 1

638 CH ₂ CN CFs R-41 .8 676 CH ₂ CN CFs R-44.12

639 CH ₂ CN CFs R-41 .9 677 CH ₂ CN CFs R-44.13

640 CH ₂ CN CFs R-41 .10 678 CH ₂ CN CFs R-44.14

641 CH ₂ CN CFs R-41.1 1 679 CH ₂ CN CFs R-44.15

642 CH ₂ CN CFs R-41.12 680 CH ₂ CN CFs R-44.16

643 CH ₂ CN CFs R-41 .13 681 CH ₂ CN CFs R-44.17

644 CH ₂ CN CFs R-41 .14 682 CH ₂ CN CFs R-44.18

645 CH ₂ CN CFs R-41 .15 683 CH ₂ CN CFs R-44.19

646 CH ₂ CN CFs R-41 .16 684 CH ₂ CN CFs R-44.20

647 CH ₂ CN CFs R-41 .17 685 CH ₂ CN CFs R-44.21

648 CH ₂ CN CFs R-41 .18 686 CH ₂ CN CFs R-44.22

649 CH ₂ CN CFs R-41 .19 687 CH ₂ CN CFs R-44.23

650 CH ₂ CN CFs R-41 .20 688 CH ₂ CN CFs R-44.24

651 CH ₂ CN CFs R-42.1 689 CH ₂ CN CFs R-44.25

652 CH ₂ CN CFs R-42.2 690 CH ₂ CN CFs R-44.26

653 CH ₂ CN CFs R-42.3 691 CH ₂ CN CFs R-44.27

654 CH ₂ CN CFs R-42.4 692 CH ₂ CN CFs R-44.28

655 CH ₂ CN CFs R-42.5 693 CH ₂ CN CFs R-44.29

656 CH ₂ CN CFs R-42.6 694 CH ₂ CN CFs R-44.30

657 CH ₂ CN CFs R-42.7 695 CH ₂ CN CFs R-44.31

658 CH ₂ CN CFs R-42.8 696 CH ₂ CN CFs R-44.32

659 CH ₂ CN CFs R-43.1 697 CH ₂ CN CFs R-44.33

660 CH ₂ CN CFs R-43.2 698 CH ₂ CN CFs R-44.34

661 CH ₂ CN CFs R-43.3 699 CH ₂ CN CFs R-44.35

662 CH ₂ CN CFs R-43.4 700 CH ₂ CN CFs R-44.36

663 CH ₂ CN CFs R-43.5 701 CH ₂ CN CFs R-44.37

664 CH ₂ CN CFs R-43.6 702 CH ₂ CN CFs R-44.38

665 CH ₂ CN CFs R-44.1 703 CH ₂ CN CFs R-44.39

666 CH ₂ CN CFs R-44.2 704 CH ₂ CN CFs R-44.40

667 CH ₂ CN CFs R-44.3 705 C-C3H5 CHs R-4.1

668 CH ₂ CN CFs R-44.4 706 C-C3H5 CHs R-4.2

669 CH ₂ CN CFs R-44.5 707 C-C3H5 CHs R-4.3

670 CH ₂ CN CFs R-44.6 708 C-C3H5 CHs R-4.4

671 CH ₂ CN CFs R-44.7 709 C-C3H5 CHs R-4.5

672 CH ₂ CN CFs R-44.8 710 C-C3H5 CHs R-4.6

673 CH ₂ CN CFs R-44.9 71 1 C-C3H5 CHs R-4.7 _R 3a _R 3b R ⁴ _R 3a _R 3b R ⁴

712 C-C3H5 CH ₃ R-4.8 750 C-C3H5 CH ₃ R-43.4

713 C-C3H5 CH ₃ R-4.9 751 C-C3H5 CH ₃ R-43.5

714 C-C3H5 CH ₃ R-4.10 752 C-C3H5 CH ₃ R-43.6

715 C-C3H5 CH ₃ R-4.1 1 753 C-C3H5 CH ₃ R-44.1

716 C-C3H5 CH ₃ R-4.12 754 C-C3H5 CH ₃ R-44.2

717 C-C3H5 CH ₃ R-40.1 755 C-C3H5 CH ₃ R-44.3

718 C-C3H5 CH ₃ R-40.2 756 C-C3H5 CH ₃ R-44.4

719 C-C3H5 CH ₃ R-41 .1 757 C-C3H5 CH ₃ R-44.5

720 C-C3H5 CH ₃ R-41 .2 758 C-C3H5 CH ₃ R-44.6

721 C-C3H5 CH ₃ R-41 .3 759 C-C3H5 CH ₃ R-44.7

722 C-C3H5 CH ₃ R-41 .4 760 C-C3H5 CH ₃ R-44.8

723 C-C3H5 CH ₃ R-41 .5 761 C-C3H5 CH ₃ R-44.9

724 C-C3H5 CH ₃ R-41 .6 762 C-C3H5 CH ₃ R-44.10

725 C-C3H5 CH ₃ R-41 .7 763 C-C3H5 CH ₃ R-44.1 1

726 C-C3H5 CH ₃ R-41 .8 764 C-C3H5 CH ₃ R-44.12

727 C-C3H5 CH ₃ R-41 .9 765 C-C3H5 CH ₃ R-44.13

728 C-C3H5 CH ₃ R-41 .10 766 C-C3H5 CH ₃ R-44.14

729 C-C3H5 CH ₃ R-41.1 1 767 C-C3H5 CH ₃ R-44.15

730 C-C3H5 CH ₃ R-41.12 768 C-C3H5 CH ₃ R-44.16

731 C-C3H5 CH ₃ R-41 .13 769 C-C3H5 CH ₃ R-44.17

732 C-C3H5 CH ₃ R-41 .14 770 C-C3H5 CH ₃ R-44.18

733 C-C3H5 CH ₃ R-41 .15 771 C-C3H5 CH ₃ R-44.19

734 C-C3H5 CH ₃ R-41 .16 772 C-C3H5 CH ₃ R-44.20

735 C-C3H5 CH ₃ R-41 .17 773 C-C3H5 CH ₃ R-44.21

736 C-C3H5 CH ₃ R-41 .18 774 C-C3H5 CH ₃ R-44.22

737 C-C3H5 CH ₃ R-41 .19 775 C-C3H5 CH ₃ R-44.23

738 C-C3H5 CH ₃ R-41 .20 776 C-C3H5 CH ₃ R-44.24

739 C-C3H5 CH ₃ R-42.1 777 C-C3H5 CH ₃ R-44.25

740 C-C3H5 CH ₃ R-42.2 778 C-C3H5 CH ₃ R-44.26

741 C-C3H5 CH ₃ R-42.3 779 C-C3H5 CH ₃ R-44.27

742 C-C3H5 CH ₃ R-42.4 780 C-C3H5 CH ₃ R-44.28

743 C-C3H5 CH ₃ R-42.5 781 C-C3H5 CH ₃ R-44.29

744 C-C3H5 CH ₃ R-42.6 782 C-C3H5 CH ₃ R-44.30

745 C-C3H5 CH ₃ R-42.7 783 C-C3H5 CH ₃ R-44.31

746 C-C3H5 CH ₃ R-42.8 784 C-C3H5 CH ₃ R-44.32

747 C-C3H5 CH ₃ R-43.1 785 C-C3H5 CH ₃ R-44.33

748 C-C3H5 CH ₃ R-43.2 786 C-C3H5 CH ₃ R-44.34

749 C-C3H5 CH ₃ R-43.3 787 C-C3H5 CH ₃ R-44.35 _R 3a _R 3b R ⁴ _R 3a _R 3b R ⁴

788 C-C3H5 CH ₃ R-44.36 826 C-C3H5 CF ₃ R-41 .20

789 C-C3H5 CH ₃ R-44.37 827 C-C3H5 CF ₃ R-42.1

790 C-C3H5 CH ₃ R-44.38 828 C-C3H5 CF ₃ R-42.2

791 C-C3H5 CH ₃ R-44.39 829 C-C3H5 CF ₃ R-42.3

792 C-C3H5 CH ₃ R-44.40 830 C-C3H5 CF ₃ R-42.4

793 C-C3H5 CF ₃ R-4.1 831 C-C3H5 CF ₃ R-42.5

794 C-C3H5 CF ₃ R-4.2 832 C-C3H5 CF ₃ R-42.6

795 C-C3H5 CF ₃ R-4.3 833 C-C3H5 CF ₃ R-42.7

796 C-C3H5 CF ₃ R-4.4 834 C-C3H5 CF ₃ R-42.8

797 C-C3H5 CF ₃ R-4.5 835 C-C3H5 CF ₃ R-43.1

798 C-C3H5 CF ₃ R-4.6 836 C-C3H5 CF ₃ R-43.2

799 C-C3H5 CF ₃ R-4.7 837 C-C3H5 CF ₃ R-43.3

800 C-C3H5 CF ₃ R-4.8 838 C-C3H5 CF ₃ R-43.4

801 C-C3H5 CF ₃ R-4.9 839 C-C3H5 CF ₃ R-43.5

802 C-C3H5 CF ₃ R-4.10 840 C-C3H5 CF ₃ R-43.6

803 C-C3H5 CF ₃ R-4.1 1 841 C-C3H5 CF ₃ R-44.1

804 C-C3H5 CF ₃ R-4.12 842 C-C3H5 CF ₃ R-44.2

805 C-C3H5 CF ₃ R-40.1 843 C-C3H5 CF ₃ R-44.3

806 C-C3H5 CF ₃ R-40.2 844 C-C3H5 CF ₃ R-44.4

807 C-C3H5 CF ₃ R-41 .1 845 C-C3H5 CF ₃ R-44.5

808 C-C3H5 CF ₃ R-41 .2 846 C-C3H5 CF ₃ R-44.6

809 C-C3H5 CF ₃ R-41 .3 847 C-C3H5 CF ₃ R-44.7

810 C-C3H5 CF ₃ R-41 .4 848 C-C3H5 CF ₃ R-44.8

81 1 C-C3H5 CF ₃ R-41 .5 849 C-C3H5 CF ₃ R-44.9

812 C-C3H5 CF ₃ R-41 .6 850 C-C3H5 CF ₃ R-44.10

813 C-C3H5 CF ₃ R-41 .7 851 C-C3H5 CF ₃ R-44.1 1

814 C-C3H5 CF ₃ R-41 .8 852 C-C3H5 CF ₃ R-44.12

815 C-C3H5 CF ₃ R-41 .9 853 C-C3H5 CF ₃ R-44.13

816 C-C3H5 CF ₃ R-41 .10 854 C-C3H5 CF ₃ R-44.14

817 C-C3H5 CF ₃ R-41.1 1 855 C-C3H5 CF ₃ R-44.15

818 C-C3H5 CF ₃ R-41.12 856 C-C3H5 CF ₃ R-44.16

819 C-C3H5 CF ₃ R-41 .13 857 C-C3H5 CF ₃ R-44.17

820 C-C3H5 CF ₃ R-41 .14 858 C-C3H5 CF ₃ R-44.18

821 C-C3H5 CF ₃ R-41 .15 859 C-C3H5 CF ₃ R-44.19

822 C-C3H5 CF ₃ R-41 .16 860 C-C3H5 CF ₃ R-44.20

823 C-C3H5 CF ₃ R-41 .17 861 C-C3H5 CF ₃ R-44.21

824 C-C3H5 CF ₃ R-41 .18 862 C-C3H5 CF ₃ R-44.22

825 C-C3H5 CF ₃ R-41 .19 863 C-C3H5 CF ₃ R-44.23 _R 3a _R 3b R ⁴

874 C-C3H5 CF ₃ R-44.34

875 C-C3H5 CF ₃ R-44.35

876 C-C3H5 CF ₃ R-44.36

877 C-C3H5 CF ₃ R-44.37

878 C-C3H5 CF ₃ R-44.38

879 C-C3H5 CF ₃ R-44.39

880 C-C3H5 CF ₃ R-44.40

C-C3H5: cyclopropyl

The compounds of formula (I) according to the present invention can be prepared e.g. according the preparation methods and preparation schemes as described below. Compounds of formula (I) according to the present invention can be prepared by standard methods of organic chemistry e.g. by the preparation methods and preparation schemes as described below. The definitions of Het, X, R ¹ , R ² , R ^3a , R ^3b and R ⁴ of the molecular structures given in the following schemes are as defined above. Room temperature means a temperature range between about 20 and 25 °C.

Compounds of formula I can be prepared by reaction of an amidine compound of the formula (II) with a carboxylic acid compound of formula (III) as outlined in scheme 1. In compounds of formula (III), Z refers to a suitable leaving group to facilitate the reaction. The transformation is preferably carried out in polar solvents such as acetonitrile, acetone, tetrahydrofuran, Ν,Ν-dimethylformamide, or in an inert solvent such as dichloromethane, 1 ,2- dichloroethane, or 1 ,2-dimethoxyethane, in particular at temperatures ranging between room temperature and the reflux temperature of the solvent. Examples of suitable leaving groups Z in formula (III) include, but are not limited to, halogen, such as fluorine, chlorine or bromine, alkyl sulfonate such as mesylate, haloalkyl sulfonate, such as trifluoromethansulfonate, alkyl phosphonate, and various activated esters derived from the reaction of the free carbonic acid with a peptide coupling reagent in the presense of an amine base. Alternatively, Z can refer to an OH group, and the carboxylic acid can be activated in situ, suitable conditions for such a transformation can be found in Chem. Rev., 2011 , 111 (1 1 ), 6557-6602.

Compounds of general formula (II) can be synthesized from the reaction of a primary or secondary amine of formula (IV) with a compound of formula (V) as depicted in scheme 2. In formulal (V), the radical R is Ci-C4-alkyl, in particular methyl or ethyl. The reaction of compound is preferably carried out in polar solvents such as acetonitrile, acetone, ethanol, methanol, isopropanol, fe/7-butyl alcohol, tetrahydrofuran, Ν,Ν-dimethylformamide, N,N- dimethylacetamide, DMSO, N-metylpyrrolidine, water or in an inert solvent such as

dichloromethane, 1 ,2-dichloroethane, or 1 ,2-dimethoxyethane, in particular at temperatures ranging between room temperature and the reflux temperature of the solvent. An amine or inorganic base can be used to facilitate the reaction. Conditions for such a reaction can be found in WO 2003/9921 1 and US6344483. Compounds of formula (IV) are commercially available or can be easily synthesized, e.g. by reduction of the corresponding nitriles or carboxamides. Compounds of the formula (V) can be synthesized from the corresponding nitrile and a Ci-C4-alkanol, such as ethanol, in the presence of hydrogen chloride or other mineral acid as described in J. Org. Chem., 2001 , 66, 6756-6761.

Scheme 2:

In cases where R ⁴ is a radical NHR ^5d , the compound of formula (I) can be prepared by reaction of a compound of formula (II) with an isocyanate of the formula R ^5d -N=C=0 by analogy to the method described in US3998958.

An alternative method to synthesize compound of formula (I), where R ^3a is different from H, is described in scheme 3. In a first step, the compound of formula (I) with R ^3a = H is prepared as described in Scheme 1 , and then reacted with compound of formula (VI), to afford compounds of formula (I), where R ^3a is different from H. In scheme 2, R ^3aa in the compound of formula (VI) has one of the meanings of R ^3a which is different from hydrogen. In particular, R ^3aa represents a C-bound radical R ^3a . Y in compound of formula (VI) is suitable leaving group. Examples of suitable leaving groups Y include, but are not limited to halogen, such as fluorine, chlorine or bromine, alkyl sulfonate such as mesylate, haloalkyl sulfonate, such as

trifluoromethansulfonate and alkyl phosphonate The reaction is preferably carried out in polar solvents such as acetonitrile, acetone, fe/7-butyl alcohol, tetrahydrofuran, N,N- dimethylformamide, Ν,Ν-dimethylacetamide, DMSO, N-methylpyrrolidine, dichloromethane, 1 ,2- dichloroethane, or 1 ,2-dimethoxyethane, in particular at temperatures ranging between room temperature and the reflux temperature of the solvent in the presence of a organic or inorganic base. Suitable reaction conditions can be found in: WO2008/009360. Scheme 3.

In cases where X of formula (I) is a sulfur atom, the sulfur atom may be introduced in a subsequent step by reacting a compound of formula (I), where X is an oxygen atom, with a thio phosphorous reagent, e.g. P4-Sio-pyridine complex or Lawesson's reagent (2,4-bis-(4- methoxyphenyl)-1 ,3,2,4-dithiadiphosphetan-2,4-disulfide) or a similar 2,4-bis-(aryl)- or 2,4'- bis(alkyl)-1 ,3,2,4-dithiadiphosphetan-2,4-disulfide, preferably in polar aprotic solvents such as acetonitrile, acetone, tetrahydrofuran, Ν,Ν-dimethylformamide, or in an inert solvent such as toluene, xylene, dichloromethane, chlorobenzene, 1 ,2-dichloroethane, or 1 ,2-dimethoxyethane. The reaction temperature may range from room temperature to the reflux temperature of the solvent. Representative reaction conditions for thionation analogous substrates are given in US 2013/102568.

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

The compounds of the formula (I) are especially suitable for efficiently combating insects, in particular the following pests:

Insects from the order of the lepidopterans {Lepidoptera), for example Acronicta major, Adoxophyes orana, Aedia leucomelas, Agrotis spp. such as Agrotis fucosa, Agrotis segetum, Agrotis ypsilon; Alabama argillacea, Ant/cars/a gemmatalis, Ant/cars/a spp., Argyresthia conjugella, Autograph a gamma, Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia murinana, Cacoecia podana, Capua reticuiana, Carpocapsa pomoneiia, Cheimatobia brumata, Chilo spp. such as Chilo suppressalis; Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Clysia ambiguella, Cnaphalocerus spp., Cydia pomoneiia, Dendrolimus pini, Diaphania nit/da /is, Diatraea grandiose/la, Earias insulana, Elasmopalpus lignosellus, Ephestia cautella, Ephestia kuehniella, Eupoecilia ambiguella, Euproctis

chrysorrhoea, Euxoa spp., Evetria bouliana, Feltia spp. such as Feltia subterranean; Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Helicoverpa spp. such as Helicoverpa armigera, Helicoverpa zea; Heliothis spp. such as Heliothis armigera, Heliothis virescens, Heliothis zea; Hellula undalis, Hibernia defoliaria, Hofmannophila pseudospretella, Homona magnanima, Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma spp. such as Laphygma exigua; Leucoptera coffeeiia, Leucoptera sciteiia, Lithocoiietis biancardella, Lithophane antennata, Lobesia botrana, Loxagrotis albicosta, Loxostege sticticalis, Lymantria spp. such as Lymantria dispar, Lymantria monacha; Lyonetia clerkella, Malacosoma neustria, Mamestra spp. such as Mamestra brassicae; Mods repanda, Mythimna separata, Orgyia pseudotsugata, Oria spp., Ostrinia spp. such as Ostrinia nubilalis; Oulema oryzae, Panolis flammea, Pectinophora spp. such as

Pectinophora gossypiella; Peridroma saucia, Phalera bucephala, Phthorimaea spp. such as Phthorimaea opercuieiia; Phyiiocnistis citreiia, Pieris spp. such as Pieris brassicae, Pieris rapae; Plathypena sea bra, Plutella maculipennis, Plutella xylostella, Prod en ia spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera spp. such as Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura; Thaumatopoea pityocampa, Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp. such as Trichoplusia ni; Tuta absoluta, and Zeiraphera canadensis;

Beetles {Coleoptera), for example Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agrilus sinuatus, Agriotes spp. such as Agriotes fuscicollis, Agriotes lineatus, Agriotes obscurus; Amphimallus solstitialis, Anisandrus dispar, Anobium punctatum, Anomala

rufocuprea, Anoplophora spp. such as Anoplophora g/abr/penn/s; Anthonomus spp. such as Anthonomus grandis, Anthonomus pomorum; Anthrenus spp., Aphthona euphoridae, Apogonia spp., Athous haemorrhoidalis, Atomaria spp. such as Atomaria linearis; Attagenus spp., Aulacophora fern oral is, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as Bruchus lentis, Bruchus pisorum, Bruchus rufimanus; Byctiscus betulae, Callosobruchus chinensis, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata,

Ceuthorhynchus spp. such as Ceuthorrhynchus assimiiis, Ceuthorrhynchus napi; Chaetocnema tibialis, Cleonus mendicus, Conoderus spp. such as Conoderus vespertinus; Cosmopolites spp., Costelytra zealandica, Crioceris asparagi, Cryptorhynchus lapathi, Ctenicera ssp. such as Ctenicera destructor; Curculio spp., Dectes texanus, Dermestes spp., Diabrotica spp. such as Diabrotica 12-punctata Diabrotica speciosa, Diabrotica longicornis, Diabrotica semipunctata, Diabrotica virgifera; Epilachna spp. such as Epilachna varivestis, Epilachna vigintioctomaculata; Epitrix spp. such as Epitrix hirtipennis; Eutinobothrus brasiliensis, Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylobius abietis, Hylotrupes bajulus, Hypera brunneipennis, Hypera postica, Hypothenemus spp., Ips typographus, Lachnosterna consanguinea, Lema bilineata, Lema melanopus, Leptinotarsa spp. such as Leptinotarsa decemlineata; Limonius caiifornicus, Lissorhoptrus oryzophiius, Lissorhoptrus oryzophiius, Lixus spp., Lyctus spp. such as Lyctus bruneus; Melanotus communis, Meligethes spp. such as Meligethes aeneus; Melolontha hippocastani, Melolontha melolontha, Mig dolus spp.,

Monochamus spp. such as Monochamus alternatus; Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus,

Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema oryzae, Oxy cetonia jucunda, Phaedon cochleariae, Phyllobius pyri, Phyllopertha horticola, Phyllophaga spp., Phyllotreta spp. such as Phyllotreta chrysocephala, Phyllotreta nemorum, Phyllotreta striolata; Phyllophaga spp., Phyllopertha horticola, Pop/ilia japonica, Premnotrypes spp., Psylliodes chrysocephala, P tin us spp., Rhizobius ventralis , Rhizopertha dominica, Sitona lineatus, Sitophilus spp. such as Sitophilus granaria, Sitophilus zeamais; Sphenophorus spp. such as Sphenophorus levis;

Sternechus spp. such as Sternechus subsignatus; Symphyletes spp., Tenebrio molitor, Tribolium spp. such as Tribolium castaneum; Trogoderma spp., Tychius spp., Xylotrechus spp., and Zabrus spp. such asZabrus tenebrioides;

Flies, mosquitoes {Diptera), e.g. Aedes spp. such as Aedes aegypti, Aedes albopictus, Aedes vexans; Anastrepha ludens, Anopheles spp. such as Anopheles albimanus, Anopheles crucians, Anopheles freeborni, Anopheles gambiae, Anopheles leucosphyrus, Anopheles maculipennis, Anopheles minimus, Anopheles quadrimaculatus, Anopheles sinensis; Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Cerafitis capitata, Ceratitis capitata, Chrysomyia spp. such as Chrysomya bezziana, Chrysomya hominivorax, Chrysomya maceiiaria; Chrysops atianticus, Chrysops discalis, Chrysops siiacea, Cochliomyia spp. such as Cochliomyia hominivorax; Contarinia spp. such as Contarinia sorghicola; Cordylobia

anthropophaga, Culex spp. such as Culex nigripalpus, Culex pip/ens, Cu/ex quinquefasciatus, Culex tarsalis, Culex tritaeniorhynchus; Culicoides furens, Culiseta inornata, Culiseta melanura, Cuterebra spp., Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia spp. such as Delia antique, Delia coarctata, Delia platura, Delia radicum; Derma tobia hominis, Drosophila spp., Fannia spp. such as Fannia canicularis; Q>a \xa^ \\\ spp. such as Gasterophilus intestinalis; Geomyza Tripunctata, Glossina fuscipes, Glossina morsitans, Glossina pa/pa/is, G/ossina tach/noides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia spp. such as Hylemyia platura; Hypoderma spp. such as Hypoderma lineata; Hyppobosca spp.,

Leptoconops torrens, Liriomyza spp. such as Liriomyza sativae, Liriomyza trifolii; Lucilia spp. such as Lucilia caprina, Lucilia cuprina, Lucilia sericata; Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. such as Mayetiola destructor; Musca spp. such as Musca autumnalis, Musca domestica; Muscina stabulans, Oestrus spp. such as Oestrus ovis; Opomyza florum, Oscineiia spp. such as Oscineiia frit; Pegomya hysocyami, Phiebotomus argentipes, Phorbia spp. such as Phorbia antiqua, Phorbia brassicae, Phorbia coarctata; Prosimulium mixtum, Psila rosae, Psorophora columbiae, Psorophora discolor, Rhagoletis cerasi, Rhagoletis pomonella,

Sarcophaga spp. such as Sarcophaga haemorrhoidalis; Simuiium vittatum, Stomoxys spp. such as Stomoxys ca/citrans; Tabanus spp. such as Tabanus atratus, Tabanus bov/nus, Tabanus lineola, Tabanus similis; Tannia spp., Tipula oleracea, Tipula paludosa, and Wohlfahrtia spp.;

Thrips { Thysanoptera), e.g. Baliothrips biformis, Dichromothrips corbetti, Dichromothrips ssp., Enneothrips flavens, Frankliniella spp. such as Frankliniella fusca, Frankliniella

occidentalis, Frankliniella tritici; Heliothrips spp., Hercinothrips femora/is, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp. such as Scirtothrips citri; Taeniothrips cardamoni, Thrips spp. such as Thrips oryzae, Thrips palmi, Thrips tabaci;

Termites (Isoptera), e.g. Calotermes flavicollis, Coptotermes formosanus, Heterotermes aureus, Heterotermes longiceps, Heterotermes tenuis, Leucotermes flavipes, Odontotermes spp., Reticulitermes spp. such as Reticulitermes speratus, Reticulitermes flavipes,

Reticulitermes grassei, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes virgin icus; Termes natalensis;

Cockroaches (Blattaria - Blattodea), e.g. Acheta domesticus, Blatta orientalis, Blattella asahinae, Blattella germanica, Gryllotalpa spp., Leu cop ha ea maderae, Locus ta spp., Melanoplus spp., Periplaneta americana, Periplaneta australasiae, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta japonica;

Bugs, aphids, leafhoppers, whiteflies, scale insects, cicadas (Hemiptera), e.g.

Acrosternum spp. such as Acrosternum hilare; Acyrthosipon spp. such as Acyrthosiphon onobrychis, Acyrthosiphon pisum; Adelges laricis, Aeneolamia spp., Agonoscena spp.,

Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anasa tristis, Antestiopsis spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphidula nasturtii, Aphis spp. such as Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis grossulariae, Aphis pom/, Aphis sambuci, Aphis schneideri, Aphis spiraecoia; Arboridia apicaiis, Ariius critatus, Aspidieiia spp., Aspidiotus spp., Atanus spp., Au/acorthum so/ani, Bemisia spp. such as Bemisia argentifolii, Bemisia tabaci; Blissus spp. such as Blissus leucopterus; Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Calocoris spp., Campylomma livid a,

Capitophorus horn/, Carneocephala fulgida, Cavelerius spp., Ceraplastes spp., Ceratovacuna lanigera, Cercopidae, Cerosipha gossypii, Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Cimex spp. such as Cimex hemipterus, Cimex lectularius; Coccomytilus halli, Coccus spp., Creontiades dilutus, Cryptomyzus ribis, Cryptomyzus rib is, Cyrtopeltis notatus, Dalbulus spp., Dasynus piperis, Dialeurades spp., Diaphorina spp., Diaspis spp., Dichelops furcatus, Diconocoris hewetti, Dora/is spp., Dreyfus/a nordmann/anae, Dreyfus/a p/ceae, Drosicha spp., Dysaphis spp. such as Dysaphis plantaginea, Dysaphis pyri, Dysaphis radicola; Dysaulacorthum pseudoso/ani, Dysdercus spp. such as Dysdercus c/ngu/atus, Dysdercus intermedius;

Dysm/coccus spp., Empoasca spp. such as Empoasca fabae, Empoasca so/ana; Er/osoma spp., Erythroneura spp., Eurygaster spp. such as Eurygaster integriceps; Eusce/is b/iobatus, Eusch/stus spp. such as Eusch/stuos heros, Eusch/stus impictiventris, Euschistus servus;

Geococcus coffeae, Halyomorpha spp. such as Halyomorpha halys; Heliopeltis spp.,

Homalodisca coagulata, Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lactucae, lcerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Leptocorisa spp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp. such as Lygus hesperus, Lygus lineolaris, Lygus pratensis; Macropes excavatus, Macrosiphum spp. such as Macrosiphum rosae, Macrosiphum a venae, Macrosiphum euphorbiae; Mahanarva fimbriolata, Megacopta cribraria, Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari, Metcafiella spp., Metopolophium dirhodum, Miridae spp., Monellia costalis, Monelliopsis pecanis, Myzus spp. such as Myzus ascalonicus, Myzus cerasi, Myzus persicae, Myzus varians; Nasonovia ribis-nigri, Nephotettix spp. such as Nephotettix maiayanus, Nephotettix nigropictus, Nephotettix parvus, Nephotettix virescens; Nezara spp. such as Nezara viridula; Nilaparvata lugens, Oebalus spp., Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp. such as Pemphigus bursarius; Pentomidae, Peregrinus maidis, Perkinsiella saccharic/da, Phenacoccus spp., Ph/oeomyzus passe rinii, Phorodon humuli, Phylloxera spp., Piesma quadrata, Piezodorus spp. such as Piezodorus guildinii, Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyri for mis, P sail us seriatus, Pseudacysta persea, Pseudaulacaspis pentagona, Pseudococcus spp. such as Pseudococcus comstocki; Psylla spp. such as Psylla mali, Psylla piri; Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Reduvius senilis, Rhodnius spp., Rhopalomyzus ascalonicus, Rhopalosiphum spp. such as Rhopalosiphum pseudobrassicas, Rhopalosiphum insertum, Rhopalosiphum maidis, Rhopalosiphum pad/; Sagatodes spp., Sahlbergella singularis, Saissetia spp., Sappaphis mala, Sappaphis mali, Scaphoides titanus, Schizaphis gram in um, Schizoneura lanuginosa, Scotinophora spp., Selenaspidus articulatus, Sitobion a venae, Sogata spp., Sogatella furcifera, Solubea insularis , Stephanitis nashi, Stictocephala festina, Tenalaphara malayensis, Thyanta spp. such as Thyanta perditor; Tibraca spp.,

Tinocaliis caryaefoiiae, Tomaspis spp., Toxoptera spp. such as Toxoptera aurant/i; ! rialeurodes spp. such as Tr/a/eurodes vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. such as Unaspis yanonensis; and Viteus vitifolii;

Ants, bees, wasps, sawflies (Hymenoptera), e.g. Athalia rosae, Atta capiguara, Atta cephalotes, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Bombus spp., Camponotus floridanus, Crematogaster spp., Dasymutilla occidental is, Di prion spp., Dolichovespula maculata, Hoplocampa spp. such as Hoplocampa minuta, Hoplocampa testudinea; Lasius spp. such as Las/us niger, Linepithema humi/e, Monomorium pharaonis, Paravespula germanica, Paravespula pennsylvanica, Paravespula vulgaris, Pheidole megacephala, Pogonomyrmex barbatus, Pogonomyrmex californicus, Polistes rubiginosa, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Vespa spp. such as Vespa crabro, and Vespula squamosal;

Crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica, Calliptamus italicus, Chortoicetes termini fera, Dociostaurus maroccanus, Gryiiotaipa africana, Gryiiotaipa gryiiotaipa, Hieroglyphus daganensis, Kraussaria angulifera, Locus ta migratoria, Locus tana pardalina, Me Ian op/us bivittatus, Mela no pi us femurrubrum, Mela no pi us mexicanus, Mela no pi us sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Oedaleus senegalensis, Schistocerca americana, Schistocerca gregaria, Tachycines asynamorus, and Zonozerus variegatus;

Earwigs {Dermaptera), e.g. forficula auricularia,

Lice {Phthiraptera), e.g. Damalinia spp., Pedicuius spp. such as Pedicuius humanus capitis, Pedicuius humanus corporis; Pthirus pubis, Haematopinus spp. such as Haematopinus eurysternus, Haematopinus suis, Linognathus spp. such as Linognathus vituli; Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp.;

Fleas {Siphonaptera), e.g. Ceratophyllus spp., Ctenocephalides felis, Ctenocephalides cam ^' s, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fascia tus.

The compounds of the formula (I) are also suitable for efficiently combating arthropd pests different from insects such as, in particular the following pests:

arachnids {Arachnida), such as acari,e.g. of the families Argasidae, Ixodidae and

Sarcoptidae, such as Amblyomma spp. (e.g. Amblyomma americanum, Amblyomma

variegatum, Amblyomma maculatum), Argas spp. (e.g. Argas persicus), Boophilus spp. (e.g. Boophilus annulatus, Boophilus deco/ora tus, Boophilus micro pi us), Dermacentor sil varum, Dermacentor andersoni, Dermacentor variabilis, Hyalomma spp. (e.g. Hyalomma truncatum), Ixodes spp. (e.g. Ixodes ricinus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus), Ornithodorus spp. (e.g. Ornithodorus moubata, Ornithodorus hermsi, Ornithodorus turicata), Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae,

Psoroptes spp. (e.g. Psoroptes ovis) , Rhipicephalus spp. (e.g. Rhipicephalus sanguineus,

Rhipicephalus appendiculatus, Rhipicephalus evertsi), Rhizoglyphus spp., Sarcoptes spp. (e.g. Sarcoptes scabiei), and Eriophyidae spp. such as Acaria she/doni, Aculops spp. (e.g. Aculops pelekassi) Aculus spp. (e.g. Aculus schlechtendali), Epitrimerus pyri, Phyllocoptruta oleivora and Eriophyes spp. (e.g. Eriophyes sheldonl); Tarsonemidae spp. such as Hemitarsonemus spp., Phytonemus pa Hid us and Polyphagotarsonemus latus, Stenotarsonemus spp:,

Tenuipalpidae spp. such as Brevipalpus spp. (e.g. Brevipalpus phoenicis); Tetranychidae spp. such as Eotetranychus spp., Eutetranychus spp., Oligonychus spp., Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae; Bryobia praetiosa, Panonychus spp. (e.g. Panonychus ulmi, Panonychus citri), Metatetranychus spp. and Oligonychus spp. (e.g. Oligonychus pratensis), Vasates lycopersici, Araneida, e.g. Latrodectus mactans, and Loxosceles reclusa. And Acarus siro, Chorioptes spp., Scorpio maurus,

Silverfish, firebrat { Thysanura), e.g. Lepisma saccharina and Thermobia domestica;

Centipedes {Chilopoda), e.g. Geophilus spp., Scutigera spp. such as Scutigera coleoptrata,

Millipedes {Diplopoda), e.g. Blaniulus guttulatus, Narceus spp.,

Springtails (Collembola ), e.g. Onychiurus ssp. such as Onychiurus armatus,

They are also suitable for controlling nematodes: plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifoiii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species such as Aphelenchoides besseyi ^' ; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus lignicolus Mamiya et Kiyohara, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species,

Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaciand other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, He/iocoty/enchus mu/ticinctus 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, Pratyienchus brachyurus, Pratyienchus negiectus, Pratyienchus penetrans, Pratyienchus curvitatus, Pratyienchus goodeyiand other Pratyienchus species; Burrowing nematodes, Radopho/us simi/is and other Radopholus species; Reniform nematodes,

Roty/enchus robustus, Roty/enchus reniformis 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 such as T ylenchulus semipenetrans, Dagger nematodes, Xiphinema species; and other plant parasitic nematode species.

Examples of further pest species which may be controlled by compounds of fomula (I) include: from the class of the Bivalva, for example, Dreissena spp.; from the class of the Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.; from the class of the helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis,

Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp. such as Haemonchus contortus; Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp.,

Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercora lis, Stronyloides spp., Taenia saginata, Taenia solium, Trichineiia spiralis, Trichineiia nativa, Trichineiia britovi, Trichineiia nelsoni, Trichineiia pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti; from the order of the Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of the Symphyla, for example, Scutigerella immaculata.

Further examples of pest species which may be controlled by compounds of formula (I) include: Anisoplia austriaca, Apamea spp., Austroasca viridigrisea, Baliothrips biformis,

Caenorhabditis elegans, Cephus spp., Ceutorhynchus napi, Chaetocnema a rid u la, Chilo auricilius, Chilo indicus , Chilo polychrysus, Chortiocetes terminifera, Cnaphalocroci medinalis, Cnaphalocrosis spp., Colias eurytheme, Collops spp., Cornitermes cumulans, Creontiades spp., Cyclocephala spp., Dalbulus ma id is, Deraceras reticu latum , Diatrea saccharalis, Dichelops furcatus, Dicladispa armigera , Diloboderus spp. such as DHoboderus abderus; Edessa spp., Epinotia spp., Formicidae, Geocoris spp., Globitermes sulfureus, Gryllotalpidae, Halotydeus destructor, Hipnodes bicolor, Hydrellia philippina, Julus spp., Laodelphax spp., Leptocorsia acuta , Leptocorsia oratorius , Liogenys fuscus, Luciiiia spp., Lyogenys fuscus, Mahanarva spp., Maladera matrida, Marasmia spp., Mastotermes spp., Mealybugs, Megascelis ssp, Metamasius hemipterus, Micro theca spp., Mods latipes, Murgantia spp., Mythemina separata ,

Neocapritermes opacus, Neocapritermes parvus, Neomegalotomus spp., Neotermes spp.,

Nymphula depunctalis, Oebalus pugnax, Orseolia spp. such as Orseolia oryzae; Oxycaraenus hyalinipennis, Plusia spp., Pomacea canaliculata, Procornitermes ssp, Procornitermes triad fer , Psylloides spp., Rachiplusia spp., Rhodopholus spp., Scaptocoris castanea, Scaptocoris spp., Scirpophaga spp. such as Scirpophaga incertulas , Scirpophaga innotata; Scotinophara spp. such as Scotinophara coarctata; Sesamia spp. such as Sesamia inferens, Sogaella frucifera, Solenapsis geminata, Spissistilus spp., Stalk borer, Stenchaetothrips biformis,

Steneotarsonemus sp/nk/, Sylepta derogata, Telehin licus, Trichostrongylus spp..

Compounds of the formula (I) are particularly useful for controlling insects of the orders Hemiptera and Thysanoptera.

For use in a method according to the present invention, the compounds of the formula (I) can be converted into the customary formulations, e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules and directly sprayable solutions. The use form depends on the particular purpose and application method. Formulations and application methods are chosen to ensure in each case a fine and uniform distribution of the compound of the formula (I) according to the present invention.

The formulations are prepared in a known manner (see e.g. for review US 3,060,084, EP-A 707 445 (for liquid concentrates), Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and et seq. WO 91/13546, US 4,172,714, US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701 , US 5,208,030, GB 2,095,558, US 3,299,566, Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961 , Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H., Grubemann, A., Formulation technology, Wiley VCH Verlag GmbH, Weinheim (Germany), 2001 , 2. D. A. Knowles, Chemistry and Technology of Agrochemical Formulations, Kluwer Academic

Publishers, Dordrecht, 1998 (ISBN 0-7514-0443-8), for example by extending the active compound with auxiliaries suitable for the formulation of agrochemicals, such as solvents and/or carriers, if desired emulsifiers, surfactants and dispersants, preservatives, antifoaming agents, anti-freezing agents, for seed treatment formulation also optionally colorants and/or binders and/or gelling agents.

Solvents/carriers, which are suitable, are e.g.:

solvents such as water, aromatic solvents (for example Solvesso products, xylene and the like), paraffins (for example mineral fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (N-metyhl-pyrrolidone (NMP),N-octylpyrrolidone NOP), acetates (glycol diacetate), alkyl lactates, lactones such as g-butyrolactone, glycols, fatty acid

dimethylamides, fatty acids and fatty acid esters, triglycerides, oils of vegetable or animal origin and modified oils such as alkylated plant oils. In principle, solvent mixtures may also be used.

carriers such as ground natural minerals and ground synthetic minerals, such as silica gels, finely divided silicic acid, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers. Suitable emulsifiers are nonionic and anionic emulsifiers, for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates.

Examples of dispersants are lignin-sulfite waste liquors and methylcellulose.

Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of

naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers,

tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, Also anti-freezing agents such as glycerin, ethylene glycol, propylene glycol and bactericides such as can be added to the formulation.

Suitable antifoaming agents are for example antifoaming agents based on silicon or magnesium stearate.

Suitable preservatives are for example dichlorophen und benzyl alcohol hemiformal Suitable thickeners are compounds which confer a pseudoplastic flow behavior to the formulation, i.e. high viscosity at rest and low viscosity in the agitated stage. Mention may be made, in this context, for example, of commercial thickeners based on polysaccharides, such as Xanthan Gum ^® (Kelzan ^® from Kelco), Rhodopol ^® 23 (Rhone Poulenc) or Veegum ^® (from R.T. Vanderbilt), or organic phyllosilicates, such as Attaclay ^® (from Engelhardt). Antifoam agents suitable for the dispersions according to the invention are, for example, silicone emulsions (such as, for example, Silikon ^® SRE, Wacker or Rhodorsil ^® from Rhodia), long-chain alcohols, fatty acids, organofluorine compounds and mixtures thereof. Biocides can be added to stabilize the compositions according to the invention against attack by microorganisms. Suitable biocides are, for example, based on isothiazolones such as the compounds marketed under the trademarks Proxel ^® from Avecia (or Arch) or Acticide ^® RS from Thor Chemie and Kathon ^® MK from Rohm & Haas. Suitable antifreeze agents are organic polyols, for example ethylene glycol, propylene glycol or glycerol. These are usually employed in amounts of not more than 10% by weight, based on the total weight of the active compound composition. If appropriate, the active compound compositions according to the invention may comprise 1 to 5% by weight of buffer, based on the total amount of the formulation prepared, to regulate the pH, the amount and type of the buffer used depending on the chemical properties of the active compound or the active compounds. Examples of buffers are alkali metal salts of weak inorganic or organic acids, such as, for example, phosphoric acid, boronic acid, acetic acid, propionic acid, citric acid, fumaric acid, tartaric acid, oxalic acid and succinic acid.

Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin,

tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water.

Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.

Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.

In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

For seed treatment purposes, respective formulations can be diluted 2-10 fold leading to concentrations in the ready to use preparations of 0,01 to 60% by weight active compound by weight, preferably 0,1 to 40% by weight.

The compound of formula (I) can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; they are intended to ensure in each case the finest possible distribution of the active compounds according to the invention.

The following are examples of formulations:

1 . Products for dilution with water. For seed treatment purposes, such products may be

applied to the seed diluted or undiluted.

A) Water-soluble concentrates (SL, LS)

10 parts by weight of the active compound is dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other auxiliaries are added. The active compound dissolves upon dilution with water, whereby a formulation with 10 % (w/w) of active compound is obtained.

B) Dispersible concentrates (DC)

20 parts by weight of the active compound is dissolved in 70 parts by weight of

cyclohexanone with addition of 10 parts by weight of a dispersant, for example

polyvinylpyrrolidone. Dilution with water gives a dispersion, whereby a formulation with 20% (w/w) of active compounds is obtained.

C) Emulsifiable concentrates (EC) 15 parts by weight of the active compounds is dissolved in 7 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion, whereby a formulation with 15% (w/w) of active compounds is obtained.

D) Emulsions (EW, EO, ES)

25 parts by weight of the active compound is dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifier machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion, whereby a formulation with 25% (w/w) of active compound is obtained.

E) Suspensions (SC, OD, FS)

In an agitated ball mill, 20 parts by weight of the active compound is comminuted with addition of 10 parts by weight of dispersants, wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound, whereby a formulation with 20% (w/w) of active compound is obtained.

F) Water-dispersible granules and water-soluble granules (WG, SG)

50 parts by weight of the active compound is ground finely with addition of 50 parts by weight of dispersants and wetters and made as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound, whereby a formulation with 50% (w/w) of active compound is obtained.

G) Water-dispersible powders and water-soluble powders (WP, SP, SS, WS)

75 parts by weight of the active compound are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound, whereby a formulation with 75% (w/w) of active compound is obtained.

H) Gel-Formulation (GF)

In an agitated ball mill, 20 parts by weight of the active compound is comminuted with addition of 10 parts by weight of dispersants, 1 part by weight of a gelling agent wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound, whereby a formulation with 20% (w/w) of active compound is obtained.

2. Products to be applied undiluted for foliar applications. For seed treatment purposes, such products may be applied to the seed diluted or undiluted.

I) Dustable powders (DP, DS)

5 parts by weight of the active compound are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product having 5% (w/w) of active compound.

J) Granules (GR, FG, GG, MG) 0.5 part by weight of the active compound is ground finely and associated with 95.5 parts by weight of carriers, whereby a formulation with 0.5% (w/w) of active compound is obtained. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted for foliar use.

K) ULV solutions (UL)

10 parts by weight of the active compound is dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product having 10% (w/w) of active compound, which is applied undiluted for foliar use.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.

The active ingredient concentrations in the ready-to-use products can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1 %.

The active ingredients may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active ingredient, or even to apply the active ingredient without additives.

In the method of this invention compounds of formula (I) may be applied with other active ingredients, for example with other pesticides, insecticides, herbicides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides. These additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix). For example, the plant(s) may be sprayed with a

composition of this invention either before or after being treated with other active ingredients.

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

M.1A carbamates, for example aldicarb, alanycarb, bendiocarb, benfuracarb,

butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or from the class of

M.1 B organophosphates, for example acephate, azamethiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O- (methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam,

methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton- methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion;

M.2. GABA-gated chloride channel antagonists such as:

M.2A cyclodiene organochlorine compounds, as for example endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), as for example ethiprole, fipronil, flufiprole, pyrafluprole and pyriprole;

M.3 Sodium channel modulators from the class of

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

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

M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class of

M.4A neonicotinoids, for example acteamiprid, chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds

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

M.4A.2: 1 -[(6-chloro-3-pyridyl)methyl]-2-nitro-1 -[(E)-pentylideneamino]guanidine; or

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

or M.4B nicotine.

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

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

M.7 Juvenile hormone mimics, such as

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

M.8 miscellaneous non-specific (multi-site) inhibitors, for example

M.8A alkyl halides as methyl bromide and other alkyl halides, or

M.8B chloropicrin, or M.8C sulfuryl fluoride, or M.8D borax, or M.8E tartar emetic;

M.9 Selective homopteran feeding blockers, for example

M.9B pymetrozine, or M.9C flonicamid;

M.10 Mite growth inhibitors, for example

M.10A clofentezine, hexythiazox and diflovidazin, or M.10B etoxazole;

M.1 1 Microbial disruptors of insect midgut membranes, for example bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. israelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1 ;

M.12 Inhibitors of mitochondrial ATP synthase, for example

M.12A diafenthiuron, or

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

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

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

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

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

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

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

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

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

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

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

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

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

M.22A indoxacarb, or M.22B metaflumizone, or M.22C 1 -[(E)-[2-(4-cyanophenyl)-1 -[3- (trifluoromethyl)phenyl]ethylidene]amino]-3-[4-(difluorometh oxy)phenyl]urea;

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

M.24 Mitochondrial complex IV electron transport inhibitors, for example

M.24A phosphine such as aluminium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide.

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

M.28 Ryanodine receptor-modulators from the class of diamides, as for example flubendiamide, chlorantraniliprole (rynaxypyr®), cyantraniliprole (cyazypyr®), or the phthalamide compounds

M.28.1 : (R)-3-Chlor-N1 -{2-methyl-4-[1 ,2,2,2-tetrafluor-1 -(trifluormethyl)ethyl]phenyl}-N2- (1 -methyl-2-methylsulfonylethyl)phthalamid and

M.28.2: (S)-3-Chlor-N1 -{2-methyl-4-[1 ,2,2,2-tetrafluor-1 -(trifluormethyl)ethyl]phenyl}-N2-

(1 -methyl-2-methylsulfonylethyl)phthalamid, or the compound M.28.3: 3-bromo-N-{2-bromo-4-chloro-6-[(1 -cyclopropylethyl)carbamoyl]phenyl}-1 -(3- chlorpyridin-2-yl)-1 H-pyrazole-5-carboxamide (proposed ISO name: cyclaniliprole), or the compound

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

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

M.28.5b) N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6- methyl-phenyl]-2- (3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxami de;

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

M.28.5d) N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carba moyl]-phenyl]-2-(3- chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;

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

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

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

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

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

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

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

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

M.28.6 N2-(1 -cyano-1 -methyl-ethyl)-N1 -(2,4-dimethylphenyl)-3-iodo-phthalamide; or M.28.7 3-chloro-N2-(1 -cyano-1 -methyl-ethyl)-N1 -(2,4-dimethylphenyl)phthalamide;

M.UN.X insecticidal active compounds of unknown or uncertain mode of action, as for example afidopyropen, azadirachtin, amidoflumet, benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite, dicofol, flufenerim, flometoquin, fluensulfone, flupyradifurone, piperonyl butoxide, pyridalyl, pyrifluquinazon, sulfoxaflor, pyflubumide or the compounds

M.UN.X.1 : 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-iso xazol-3-yl]-2-methyl- N-[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzamide, or the compound

M.UN.X.2: 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl )-4H-isoxazol-3-yl]-N- [2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]naphthalene-1 -carboxamide, or the compound M.UN.X.3: 1 1 -(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]- tetradec-1 1 -en-10-one, or the compound

M.UN.X.4: 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1 -azaspiro[4.5]dec-3- en-2-one, or the compound

M.UN.X.5: 1 -[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl ]-3-(trifluoromethyl)-

1 H-1 ,2,4-triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582); or

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

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

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

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

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

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

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

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

M.UN.X.7: 3-[3-chloro-5-(trifluoromethyl)phenyl]-4-oxo-1 -(pyrimidin-5-ylmethyl)pyrido[1 ,2- a]pyrimidin-1 -ium-2-olate; or

M.UN.X.8: 8-chloro-N-[2-chloro-5-methoxyphenyl)sulfonyl]-6-trifluorome thyl)-imidazo[1 ,2- a]pyridine-2-carboxamide; or

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

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

The commercially available compounds of the group M listed above may be found in The Pesticide Manual, 15th Edition, C. D. S. Tomlin, British Crop Protection Council (201 1 ) among other publications.

The quinoline derivative flometoquin is shown in WO 2006/013896. The aminofuranone compounds flupyradifurone is known from WO 2007/1 15644. The sulfoximine compound sulfoxaflor is known from WO 2007/149134. The pyrethroid momfluorothrin is known from US 6908945. The pyrazole acaricide pyflubumide is known from WO 2007/020986. The isoxazoline compounds have been described likewise M.UN.X.1 in WO 2005/085216, M.UN.X2. in WO 2009/002809 and in WO 201 1/149749 and the isoxazoline M.UN.X.9 in WO

2013/050317. The pyripyropene derivative afidopyropen has been described in WO

2006/129714. The spiroketal-substituted cyclic ketoenol derivative M.UN.X.3 is known from WO 2006/089633 and the biphenyl-substituted spirocyclic ketoenol derivative M.UN.X.4 from WO 2008/06791 1 . Finally triazoylphenylsulfide like M.UN.X.5 have been described in WO

2006/043635 and biological control agents on basis of bacillus firmus in WO 2009/124707. The neonicotionids 4A.1 is known from WO 20120/069266 and WO 201 1/06946, the M.4.A.2 from WO 2013/003977, the M4.A.3.from WO 2010/069266.

The Metaflumizone analogue M.22C is described in CN 10171577. The phthalamides M.28.1 and M.28.2 are both known from WO 2007/101540. The anthranilamide M.28.3 has been described in WO 2005/077934. The hydrazide compound M.28.4 has been described in WO 2007/043677. The anthranilamides M.28.5a) to M.28.5h) can be prepared as described in WO 2007/006670, WO 2013/024009 and WO 2013/024010, the anthranilamide Μ.28.5Ϊ) is described in WO 201 1/085575, the M.28.5j) in WO 2008/134969, the M.28.5k) in US

201 1/046186 and the M.28.5I) in WO 2012/034403. The diamide compounds M.28.6 and M.28.7 can be found in CN 102613183.

The compounds M.UN.X.6a) to M.UN.X.6i) listed in M.UN.X.6 have been described in WO 2012/029672. The mesoionic antagonist compound M.UN.X.7 was described in

WO 2012/0921 15, the nematicide M.UN.X.8 in WO 2013/055584 and the Pyridalyl-type analogue M.UN.X.10 in WO 2010/060379.

In another embodiment of the invention, the compounds of formula (I), or their

stereoisomers, salts, tautomers and N-oxides, may also be applied with fungicides as compound II.

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:

strobilurins: azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, triclopyricarb/chlorodincarb, trifloxystrobin, 2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methyl ester and 2 (2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N methyl-acetamide;

oxazolidinediones and imidazolinones: famoxadone, fenamidone;

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

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

F.I-3) Inhibitors of complex III at Qi site: cyazofamid, amisulbrom, [(3S,6S,7R,8R)-8-benz- yl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-meth yl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxy-pyr idine- 2-carbonyl]amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)- 8-benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy-pyridine-2-car bonyl)amino]-6-methyl-4,9-dioxo- 1 ,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[[3-(1 ,3-benzodioxol-5- ylmethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9 -dioxo-1 ,5-dioxonan-7-yl] 2- methylpropanoate, 35,65,7 ?,8 )-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]- 6-methyl-4,9-dioxo-8-(phenylmethyl)-1 ,5-dioxonan-7-yl 2-methylpropanoate;

F.I-4) Other respiration inhibitors (complex I, uncouplers) diflumetorim; (5,8-difluoro- quinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethylpyridin-2- yloxy)-phenyl]-ethyl}-amine;

tecnazen;ametoctradin; silthiofam; nitrophenyl derivates: binapacryl, dinobuton, dinocap, fluazinam, ferimzone, nitrthal-isopropyl,

and including organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide;

F.ll) Sterol biosynthesis inhibitors (SBI fungicides)

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

triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil,

paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1 -[reA(2^3 ^-3-(2-chloro- phenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato -1 H-[1 ,2,4]triazole, 2-[reA(2^3 )-3- (2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[ 1 ,2,4]triazole-3-thiol;

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

pyrimidines, pyridines and piperazines: fenarimol, nuarimol, pyrifenox, triforine, 1 -[rel-

(2^3 )-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]- 5-thiocyanato-1 H- [1 ,2,4]triazole, 2-[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxi ranylmethyl]- 2H-[1 ,2,4]triazole-3-thiol;

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

morpholines: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph; piperidines: fenpropidin, piperalin; spiroketalamines: spiroxamine; F.I 1-3) Inhibitors of 3-keto reductase: hydroxyanilides: fenhexamid;

F.lll) Nucleic acid synthesis inhibitors

F.III-1 ) RNA, DNA synthesis

phenylamides or acyl amino acid fungicides: benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl;

isoxazoles and iosothiazolones: hymexazole, octhilinone;

F.III-2) DNA topisomerase inhibitors: oxolinic acid;

F.III-3) Nucleotide metabolism (e.g. adenosin-deaminase), hydroxy (2-amino)-pyrimidines bupirimate;

F.IV) Inhibitors of cell division and or cytoskeleton

F.IV-1 ) Tubulin inhibitors: benzimidazoles and thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl;

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

F.IV-2) Other cell division inhibitors

benzamides and phenyl acetamides: diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide;

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

F.V) Inhibitors of amino acid and protein synthesis

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

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

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

antibiotics: blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxine, validamycin A;

F.VI) Signal transduction inhibitors

F.VI-1 ) MAP / Histidine kinase inhibitors (e.g. anilino-pyrimidines)

dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin;

phenylpyrroles: fenpiclonil, fludioxonil;

F.VI-2) G protein inhibitors: quinolines: quinoxyfen;

F.VI I) Lipid and membrane synthesis inhibitors

F.VI 1-1 ) Phospholipid biosynthesis inhibitors

organophosphorus compounds: edifenphos, iprobenfos, pyrazophos;

dithiolanes: isoprothiolane;

F.VII-2) Lipid peroxidation: aromatic hydrocarbons: dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole;

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

cinnamic or mandelic acid amides: dimethomorph, flumorph, mandiproamid, pyrimorph; valinamide carbamates: benthiavalicarb, iprovalicarb, pyribencarb, valifenalate and N-(1 - (1 -(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;

F.VII-4) Compounds affecting cell membrane permeability and fatty acids: 1 -[4-[4-[5-(2,6-difluorophenyl)-4,5-^

methyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl]ethanone, carbamates: propamocarb, propamocarb- hydrochlorid,

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

F.VIII) Inhibitors with Multi Site Action

F.VIII-1 ) Inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;

F.VIII-2) Thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam,

methasulphocarb, metiram, propineb, thiram, zineb, ziram;

F.VIII-3) Organochlorine compounds (e.g. phthalimides, sulfamides, chloronitriles):

anilazine, chlorothalonil, captafol, captan, folpet, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pentachlorphenole and its salts, phthalide, tolylfluanid, N-(4-chloro-2-nitro- phenyl)-N-ethyl-4-methyl-benzenesulfonamide;

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

F.VIII-5) Anthraquinones: 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, fenpyrazamine, flumetover, flusulfamide, flutianil, methasulfocarb, nitrapyrin, nitrothal-isopropyl, oxathiapiprolin, oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide, 2-butoxy-6-iodo-3- propylchromen-4-one, N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro- phenyl)- methyl)-2-phenyl acetamide, N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phen yl)-N- ethyl-N methyl formamidine, N' (4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl) -N- ethyl-N-methyl formamidine, N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy )- phenyl)-N-ethyl-N-methyl formamidine, N'-(5-difluoromethyl-2 methyl-4-(3-trimethylsilanyl- propoxy)-phenyl)-N-ethyl-N-methyl formamidine, 2-{1 -[2-(5-methyl-3-trifluoromethyl-pyrazole-1 - yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid methyl-(1 ,2,3,4-tetrahydro-naphthalen-1 -yl)- amide, 2-{1 -[2-(5-methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]-piperidin-4-yl}-thiazole-4- carboxylic acid ,2,3,4-tetrahydro-naphthalen-1 -yl-amide, methoxy-acetic acid 6-tert- butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester and N-Methyl-2-{1 -[(5-methyl-3-trifluoromethyl-1 H- pyrazol-1 -yl)-acetyl]-piperidin-4-yl}-N-[(1 )-1 ,2,3,4-tetrahydronaphthalen-1 -yl]-4- thiazolecarboxamide, 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine, pyrisoxazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro-pyrazole -1 carbothioic acid S- allyl ester, N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide, 5-chloro-1 (4,6- dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole, 2-(4-chloro-phenyl)-N-[4-(3,4- dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxyacetamide;

F.XI) Growth regulators: abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N 6-benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium), prohydrojasmon, thidiazuron,

triapenthenol, tributyl phosphorotrithioate, 2,3,5 tri iodobenzoic acid, trinexapac-ethyl and uniconazole;

F.XI I) Biological control agents

Ampelomyces quisqualis (e.g. AQ 10 ^® from Intrachem Bio GmbH & Co. KG, Germany),

Aspergillus f/avus (e.g. AFLAGUARD ^® from Syngenta, CH), Aureobasidium pullulans (e.g.

BOTECTOR ^® from bio-ferm GmbH, Germany), Bacillus pumi/us (e.g. NRRL Accession No. B-30087 in SONATA ^® and BALLAD ^® Plus from AgraQuest Inc., USA), Bacillus subtilis (e.g. isolate NRRL-Nr. B-21661 in RHAPSODY ^® , SERENADE ^® MAX and SERENADE ^® ASO from AgraQuest Inc., USA), Bacillus subtilis e, amyloliquefaciens FZB24 (e.g. TAEGRO ^® from Novozyme Biologicals, Inc., USA), Candida oleophila I-82 (e.g. ASPIRE ^® from Ecogen Inc., USA), Candida saitoana (e.g. BIOCURE ^® (in mixture with lysozyme) and BIOCOAT ^® from Micro Flo Company, USA (BASF SE) and Arysta), Chitosan (e.g. ARMOUR-ZEN from BotriZen Ltd., NZ), Clonostachys rosea f. catenulata, also named Gliocladium catenulatum (e.g. isolate J 1446: PRESTOP ^® from Verdera, Finland), Coniothyrium minitans (e.g. CONTANS ^® from Prophyta, Germany), Cryphonectria parasitica (e.g. Endothia parasitica from CNICM, France),

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

Microdochium dimerum (e.g. ANTIBOT ^® from Agrauxine, France), Phlebiopsis gigantea (e.g. ROTSOP ^® from Verdera, Finland), Pseudozyma flocculosa (e.g. SPORODEX ^® from Plant Products Co. Ltd., Canada), Pythium oligandrum DV74 (e.g. POLYVERSUM ^® from Remeslo SSRO, Biopreparaty, Czech Rep.), Reynoutria sachlinensis (e.g. REGALIA ^® from Marrone Biolnnovations, USA), Talaromyces flavus^^ M (e.g. PROTUS ^® from Prophyta, Germany), Trichoderma asperellum SKT -1 (e.g. ECO-HOPE ^® from Kumiai Chemical Industry Co., Ltd.,

Japan), T. atroviride LC52 (e.g. SENTINEL ^® from Agrimm Technologies Ltd, NZ), T. harzianum T-22 (e.g. PLANTSHIELD ^® der Firma BioWorks Inc., USA), T. harzianum JH 35 (e.g. ROOT PRO ^® from Mycontrol Ltd., Israel), T. harzianum T-39 (e.g. TRICHODEX ^® and TRICHODERMA 2000 ^® from Mycontrol Ltd., Israel and Makhteshim Ltd., Israel), T. harzianum and T. viride (e.g. TRICHOPEL from Agrimm Technologies Ltd, NZ), T. harzianum ICC012 and T. viride ICC080 (e.g. REMEDIER ^® WP from Isagro Ricerca, Italy), T. polysporum and T. harzianum (e.g. BINAB ^® from BINAB Bio-Innovation AB, Sweden), T. stromat/cum {e.g. TRICOVAB ^® from

C.E.P.L.A.C., Brazil), T. virens GL-2 (e.g. SOILGARD ^® from Certis LLC, USA), T. v/ride {e.g.

TRIECO ^® from Ecosense Labs. (India) Pvt. Ltd., Indien, BIO-CURE ^® F from T. Stanes & Co.

Ltd., Indien), T. viride ^~ V^\ (e.g. T. viride TV1 from Agribiotec srl, Italy), Ulocladium oudemansii HRU3 (e.g. BOTRY-ZEN ^® from Botry-Zen Ltd, NZ).

The commercially available compounds II of the group F listed above may be found in The

Pesticide Manual, 15th Edition, C. D. S. Tomlin, British Crop Protection Council (201 1 ) among other publications. Their preparation and their activity against harmful fungi is known (cf.:

http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by lUPAC nomenclature, their preparation and their fungicidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP A 141 317; EP-A 152 031 ;

EP A 226 917; EP A 243 970; EP A 256 503; EP-A 428 941 ; EP-A 532 022; EP-A 1 028 125;

EP-A 1 035 122; EP A 1 201 648; EP A 1 122 244, JP 2002316902; DE 19650197;

DE 10021412; DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ;

WO 01/56358; WO 02/22583; WO 02/40431 ; WO 03/10149; WO 03/1 1853; WO 03/14103;

WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491 ; WO 04/49804;

WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721 ; WO 05/87772;

WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 1 1/028657).

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

compounds/compositions to the locus of the animal pest or plant).

The compounds of formula (I), including their stereoisomers and tautomers, as well the salts thereof, or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by animal pests, especially insects, acaridae or arachnids by contacting the plant/crop with a pesticidally effective amount of compounds of formula (I). The term "crop" refers both to growing and harvested crops.

The compounds of the present invention and the compositions comprising them are particularly important in the control of a multitude of insects on various cultivated plants, such as cereal, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, 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 a insecticidally effective amount of the active compounds. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the insects.

The present invention also includes a method of combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, cultivated plants, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one active compound of the formula (I), a stereoisomers, a tautomere or a salt thereof.

Moreover, animal pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of compounds of formula (I), a stereoisomer, a tautomere or a salt thereof. As such, the application may be carried out before or after the infection of the locus, growing crops, or harvested crops by the pest.

The compounds of the invention can also be applied preventively to places at which occurrence of the pests is expected.

The compounds of formula (I), including their stereoisomers and their tautomers, as well as their salts may be also used to protect growing plants from attack or infestation by pests. The use includes contacting the plant with a pesticidally effective amount of compounds of formula (I), a stereoisomer, a tautomere or a salt thereof. As such, "contacting" includes both direct contact, i.e. applying the compounds/compositions directly on the pest and/or plant - typically to the foliage, stem or roots of the plant, and indirect contact, i.e. applying the

compounds/compositions to the locus of the pest and/or plant.

"Locus" means a habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest or parasite is growing or may grow.

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

The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-transtional modification of protein(s) (oligo- or polypeptides) poly for example by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties(e.g. as disclosed in

Biotechnol Prog. 2001 Jul-Aug;17(4):720-8., Protein Eng Des Sel. 2004 Jan;17(1 ):57-66, Nat Protoc. 2007;2(5):1225-35., Curr Opin Chem Biol. 2006 Oct;10(5):487-91 . Epub 2006 Aug 28., Biomaterials. 2001 Mar;22(5):405-17, Bioconjug Chem. 2005 Jan-Feb;16(1 ):1 13-21 ).

The term "cultivated plants" is to be understood also including plants that have been rendered tolerant to applications of specific classes of herbicides, such as

hydroxy-phenylpyruvate dioxygenase (HPPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e. g. US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imidazolinones (see e. g. US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073); enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate (see e. g. WO 92/00377); glutamine synthetase (GS) inhibitors, such as glufosinate (see e. g. EP-A-0242236, EP-A-242246) or oxynil herbicides (see e. g. US 5,559,024) as a result of conventional methods of breeding or genetic engineering. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), for example Clearfield® summer rape (Canola) being tolerant to imidazolinones, e. g. imazamox. Genetic engineering methods have been used to render cultivated plants, such as soybean, cotton, corn, beets and rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).

The term "cultivated plants" is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus

thuringiensis, such as a-endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such

Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP- glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, for example WO 02/015701 ). Further examples of such toxins or genetically-modified plants capable of synthesizing such toxins are dis-closed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 und WO 03/052073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins protection from harmful pests from certain taxonomic groups of arthropods, particularly to beetles (Coleoptera), flies (Diptera), and butterflies and moths (Lepidoptera) and to plant parasitic nematodes (Nematoda).

The term "cultivated plants" is to be understood also including plants that are, e.g. by the use of recombinant DNA techniques, capable of synthesizing one or more proteins in order 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", also termed PR proteins - see, for example EP-A 0 392 225 -, or plant disease resistance genes - for example 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, for example, in the publications mentioned above.

The term "cultivated plants" is to be understood also including plants that are, e.g. by the use of recombinant DNA techniques, capable of synthesizing one or more proteins to increase the productivity, e. g. bio mass production, grain yield, starch content, oil content or protein content, or to improve tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.

The term "cultivated plants" is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, for ex-ample oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape).

The term "cultivated plants" is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, for example potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato).

In general, "pesticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various

compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like. In the case of soil treatment or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 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 25 g to 600 g per hectare, more desirably from 50 g to 500 g per hectare.

The compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, are effective through both contact, e.g. via soil, glass, wall, bed net, carpet, plant parts or animal parts, and ingestion, e.g. via ingestion of bait or plant part.

The compounds of the invention may also be applied against non-crop insect pests, such as ants, termites, wasps, flies, mosquitos, crickets, or cockroaches. For use against said non- crop pests, compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, are preferably used in a bait composition.

The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks. Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources. Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickyness, moisture retention or aging characteristics.

The bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.

For use in bait compositions, the typical content of active ingredient is from 0.001 weight

% to 15 weight %, desirably from 0.001 weight % to 5% weight % of active compound.

Formulations of compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, as aerosols, e.g in spray cans, oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents such as lower alcohols, e.g. methanol, ethanol, propanol or butanol, ketones, e.g. acetone, methyl ethyl ketone, paraffin hydrocarbons, e.g. kerosenes or mineral oils, having boiling ranges of approximately 50 to 250°C, dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.

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

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

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

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

The compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, 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 formula (I), their stereoisomers, their tautomers or their salts 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 formula (I), including the tautomers and stereoisomers, as well as their salts, are also suitable for the treatment of seeds in order to protect the seed from insect pest, in particular from soil-living insect pests and the resulting plant's roots and shoots against soil pests and foliar insects.

The compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, are particularly useful for the protection of the seed from soil pests and the resulting plant's roots and shoots against soil pests and foliar insects. The protection of the resulting plant's roots and shoots is preferred. More preferred is the protection of resulting plant's shoots from piercing and sucking insects, wherein the protection from aphids is most preferred.

The present invention therefore comprises a method for the protection of seeds from insects, in particular from soil insects and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising contacting the seeds before sowing and/or after pregermination with a compound of the general formula (I), a tautomer, a stereosiomer or a salt thereof. Particularly preferred is a method, wherein the plant's roots and shoots are protected, more preferably a method, wherein the plants shoots are protected form piercing and sucking insects, most preferably a method, wherein the plants shoots are protected from aphids.

The term seed includes 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 includes 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 relates to seeds coated with or containing the active compound of the present invention, i.e. containing a compound of formula (I), a stereoisomer, a tautomer or a salt thereof.

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 compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, 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 compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, can be employed in treatment of seeds from plants, which are resistant to herbicides from the group consisting of the sulfonylureas, imidazolinones, glufosinate- ammonium or glyphosate-isopropylammonium and analogous active substances (see for example, EP-A-0242236, EP-A-242246) (WO 92/00377) (EP-A-0257993, U.S. Pat. No.

5,013,659) or in transgenic crop plants, for example cotton, with the capability of producing Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP-A- 0142924, EP-A-0193259),

Furthermore, the compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, 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 a compound of formula (I), a stereoisomer, a tautomer or a salt, for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the the compound of formula (I), including its tautomers and stereoisomers, or a salt thereof, from 0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g. 1 to 40 % by weight of a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.

Seed Treatment formulations may additionally also comprise binders and optionally colorants.

Binders can be added to improve the adhesion of the active materials on the seeds after treatment. Suitable binders are homo- and copolymers from alkylene oxides like ethylene oxide or propylene oxide, polyvinylacetate, polyvinylalcohols, polyvinylpyrrolidones, and copolymers thereof, ethylene-vinyl acetate copolymers, acrylic homo- and copolymers, polyethyleneamines, polyethyleneamides and polyethyleneimines, polysaccharides like celluloses, tylose and starch, polyolefin homo- and copolymers like olefin/maleic anhydride copolymers, polyurethanes, polyesters, polystyrene homo and copolymers

Optionally, also colorants can be included in the formulation. Suitable colorants or dyes for seed treatment formulations are Rhodamin B, C.I. Pigment Red 1 12, C.I. Solvent Red 1 , pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.

Examples of a gelling agent is carrageen (Satiagel ^® )

In the treatment of seed, the application rates of the compounds of formula (I) are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed.

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

The compounds of formula (I), including their stereoisomers and their tautomers, and the veterinarily acceptable salts thereof are in particular also suitable for being used for combating parasites in and on animals.

An object of the present invention is 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 control of the parasites.

The invention also relates to compositions containing a parasiticidally effective amount of a compound of formula (I) or a stereoisomer or a tautomer or a veterinarily acceptable salt thereof and an acceptable carrier, for combating parasites in and on animals.

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

The invention also provides a process for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises a parasiticidally effective amount of a compound of formula (I) or a stereoisomer or a tautomer or a veterinarily acceptable salt thereof or a composition comprising it.

Activity of compounds against agricultural pests does not suggest their suitability for control of endo- and ectoparasites in and on animals which requires, for example, low, non- emetic 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), including their stereoisomers and tautomers, and the salts thereof, are suitable for combating endo- and ectoparasites in and on animals.

Compounds of formula (I), including their stereoisomers and their tautomers, and the veterinarily acceptable salts thereof, and compositions comprising them are preferably used for controlling and preventing infestations and infections animals including warm-blooded animals, including humans, and fish. They are for example suitable for controlling and preventing infestations and infections in mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels. Compounds of formula (I), including their stereoisomers and their tautomers, and the veterinarily acceptable salts thereof and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals, such as dogs or cats.

Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.

The compounds of formula (I), including their stereoisomers and their tautomers, and the veterinarily acceptable salts thereof and compositions comprising them are suitable for systemic and/or non-systemic control of ecto- and/or endoparasites. They are active against all or some stages of development.

The compounds of formula (I) including their stereoisomers and their tautomers, and the veterinarily acceptable salts thereof are especially useful for combating ectoparasites.

The compounds of formula (I), including their stereoisomers and their tautomers, and the veterinarily acceptable salts thereof are especially useful for combating parasites of the following orders and species, respectively:

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides cam ^' s, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fascia tus;

cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae,

Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orien talis;

flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans,

Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya ma eel I aria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pip/ens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Cu/iseta me/anura, Derma tobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina pa/pa/is, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris,

Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lu cilia caprina, Lu cilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor,

Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys caicitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus simiiis; lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus;

ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephaius sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma macula turn, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti ^' and Dermanyssus gallinae,

Actinedida (Prostigmata) und Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp.,

Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp.,

Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., and Laminosioptes spp;

Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Arilus critatus;

Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and

Solenopotes spp.;

Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicoia spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp;

Roundworms Nematoda:

Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), ^Trichuridae^ Trichuris spp., Capillaria spp.;

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

Strongylida, e.g. Strongylus spp., Ancyiostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp. , Cooper/a spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus , Syngamus trachea, Ancyiostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongyius spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus, and Dioctophyma renale;

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

Camallanida, e.g. Dracunculus medinensis (guinea worm);

Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetaionema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.;

Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp.,

Macracanthorhynchus hirudinaceus and Oncicola spp;

Planarians (Plathelminthes):

Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp.,

Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp;

Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium can/hum, Multiceps spp., Hymenolepis spp.,

Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp. The compounds of formula (I), including their stereoisomers and their tautomers, and the salts thereof and compositions containing them are particularly useful for the control of pests from the orders Diptera, Siphonaptera and Ixodida.

Moreover, the use of the compounds of formula (I), including their stereoisomers and their tautomers, and the salts thereof and compositions containing them for combating mosquitoes is especially preferred.

The use of the compounds of formula (I), including their stereoisomers and their tautomers, and the salts thereof and compositions containing them for combating flies is a further preferred embodiment of the present invention.

Furthermore, the use of the compounds of formula (I), including their stereoisomers and their tautomers, and the salts thereof and compositions containing them for combating fleas is especially preferred.

The use of the compounds of formula (I), including their stereoisomers and their tautomers, and the salts thereof and compositions containing them for combating ticks is a further preferred embodiment of the present invention.

The compounds of formula (I), including their stereoisomers and their tautomers, and the salts thereof also are especially useful for combating endoparasites (roundworms nematoda, thorny headed worms and planarians).

Administration can be carried out both prophylactically and therapeutically.

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

For oral administration to warm-blooded animals, the compounds of the present invention may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the compounds of the present invention may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula (I) compound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.

Alternatively, the compounds of the present invention may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The compounds of the present invention may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of the present invention may be formulated into an implant for subcutaneous administration. In addition the compounds of the present invention may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of a compound of the present invention.

The compounds of the present invention may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the compounds of the present invention. In addition, the compounds of the present invention may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.

Suitable preparations are:

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

Emulsions and suspensions for oral or dermal administration; semi-solid preparations; Formulations in which the active compound is processed in an ointment base or in an oil-in- water or water-in-oil emulsion base;

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

Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further ingredients such as acids, bases, buffer salts, preservatives, and solubilizers. The solutions are filtered and filled sterile.

Suitable solvents are physiologically tolerable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methyl- pyrrolidone, 2-pyrrolidone, and mixtures thereof.

The compounds of the present invention can optionally be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.

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

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

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

Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.

Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.

Further suitable solvents are polypropylene glycol, phenyl ethanol, phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate, ethers such as alkyleneglycol alkylether, e.g. dipropylenglycol monomethylether, ketons such as acetone, methylethylketone, aromatic hydrocarbons, vegetable and synthetic oils, dimethylformamide, dimethylacetamide, transcutol, solketal, propylencarbonate, and mixtures thereof.

It may be advantageous to add thickeners during preparation. Suitable thickeners are inorganic thickeners such as bentonites, colloidal silicic acid, aluminium monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates. Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency results. The thickeners employed are the thickeners given above.

Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically.

Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added.

Suitable solvents are, for example, water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol mono-butyl ether, ketones such as acetone, methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, n-alkylpyrrolidones such as methylpyrrolidone, n- butylpyrrolidone or n-octylpyrrolidone, N-methylpyrrolidone, 2-pyrrolidone, 2,2-dimethyl-4-oxy- methylene-1 ,3-diox- olane and glycerol formal.

Suitable colorants are all colorants permitted for use on animals and which can be dissolved or suspended.

Suitable absorption-promoting substances are, for example, DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and copolymers thereof with polyethers, fatty acid esters, triglycerides, fatty alcohols.

Suitable antioxidants are, for example, sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol.

Suitable light stabilizers are, for example, novantisolic acid.

Suitable adhesives are, for example, cellulose derivatives, starch derivatives,

polyacrylates, natural polymers such as alginates, gelatin.

Emulsions can be administered orally, dermally or as injections.

Emulsions are either of the water-in-oil type or of the oil-in-water type.

They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances.

Suitable hydrophobic phases (oils) are, for example: liquid paraffins, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic/capric biglyceride, triglyceride mixture with vegetable fatty acids of the chain length Cs- Ci2 or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids possibly also containing hydroxyl groups, mono- and diglycerides of the Cs-C-io fatty acids, fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol perlargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C16-C18, isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated fatty alcohols of chain length C12-C18, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters such as synthetic duck coccygeal gland fat, dibutyl phthalate, diisopropyl adipate, and ester mixtures related to the latter, fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and fatty acids such as oleic acid and mixtures thereof.

Suitable hydrophilic phases are, for example, water, alcohols such as propylene glycol, glycerol, sorbitol and mixtures thereof.

Suitable emulsifiers are, for example,

non-ionic surfactants, e.g. polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether;

ampholytic surfactants such as di-sodium N-lauryl-p-iminodipropionate or lecithin; - anionic surfactants, such as sodium lauryl sulfate, fatty alcohol ether sulfates,

mono/dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt; cation-active surfactants, such as cetyltrimethylammonium chloride.

Suitable further auxiliaries are substances which enhance the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes, colloidal silicic acid or mixtures of the substances mentioned.

Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances,

preservatives, antioxidants, light stabilizers.

Liquid suspending agents are all homogeneous solvents and solvent mixtures.

Suitable wetting agents (dispersants) are the emulsifiers given above.

Other auxiliaries, which may be mentioned, are those given above.

Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.

For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.

Suitable excipients are all physiologically tolerable solid inert substances. Those used are inorganic and organic substances. Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, hydrogencarbonates, aluminium oxides, titanium oxide, silicic acids, argillaceous earths, precipitated or colloidal silica, or phosphates. Organic substances are, for example, sugar, cellulose, foodstuffs and feeds such as milk powder, animal meal, grain meals and shreds, starches.

Suitable auxiliaries are preservatives, antioxidants, and/or colorants which have been mentioned above. Other suitable auxiliaries are lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonites, disintegration-promoting substances such as starch or crosslinked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone, and dry binders such as microcrystalline cellulose.

In general, "parasiticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.

The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of a compound of formula (I), a stereoisomer, a tautomer or a salt thereof.

Generally it is favorable to apply the compounds of the present invention in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.

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

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

Furthermore, the preparations for controlling endoparasites comprise a compound of the present invention usually in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 per cent by weight, very particularly preferably of 0.005 to 0.25 per cent by weight.

In a preferred embodiment of the present invention, the compositions comprising the a compound of the present invention are applied dermally / topically.

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

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

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

The following abbreviations are used:

TFA: trifluoroacetic acid

EtOH: ethanol

EtOAc: ethyl acetate

DIEA: diisopropyl ethylamine

PyBrop: bromotripyrrolidinophosphonium hexafluorophosphate

HPLC: High Performance Liquid Chromatography

MS: Mass spectrometry

MeOH: methanol

t.R = retention time

The compound examples were characterized by coupled High Performance Liquid Chromatography with mass spectrometry (HPLC/MS) or by their melting point.

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

HPLC method 1 : Phenomenex Kinetex 1.7 μηη XB-C18 100A; 50 x 2.1 mm; mobile phase: A: water + 0.1 % trifluoroacetic acid (TFA); B: acetonitrile + 0.1 % TFA; gradient: 5-100% B in 1 .50 minutes; 100% B 0.20 min; flow: 0.8-1.OmI/min in 1.50 minutes at 60°C.MS: quadrupole electrospray ionization, 80 V (positive mode);

HPLC method 2: Analytical HPLC column 1 : RP-18 column Chromolith Speed ROD (from Merck KgaA, Germany). Elution: acetonitrile + 0.1 % TFA acid/ water + 0.1 % TFA in a ratio of from 5:95 to 95:5 in 5 minutes at 40 °C.

MS-method: ESI positive

A. Preparation examples

General procedure:

1 . Preparation of N-[(6-chloropyridyl-3-yl)methyl]-N-methyl acetamidine

A solution of ethyl ethanimidate hydrochloride (10 mmol) and 1 -(6-chloro-3-pyridyl)-N- methyl-methanamine (10 mmol) in EtOH (20 mL) was stirred at room temperature for 15 hrs. The reaction was then concentrated in vacuo, and the resulting residue is tritrated with diethyl ether, and filtered to obtain the desired product.

2. Preparation of N-[1 -[(6-chloropyridyl-3-yl)methyl]-methylamino]ethyliden acylamides (l-A.1 aa) (compounds of the formula I, wherein Het is 6-chloropyridin-3-yl, R ¹ = R ² = H, R ^3b = CHs and X is O)

To a solution of the acid (10 mmol) of the formula (2), N-[(6-chloro-3-pyridyl)methyl]-N- methyl-acetamidine (1 1 mmol) of the formula (1 ), and PyBrop (12.50 mmol) in CH2CI2 (20 mL) at 0 °C DIEA (40 mmol) was added in a dropwise manner. The reaction mixture was then allowed to stir at room temperature for 15 hours. The reaction mixture was then diluted with saturated aqueous NaHCOs, phases are separated, and the organic phase is extracted twice with CH2CI2, dried over Na2S0 ₄ , filtered and concentrated in vacuo. The product of the formula (l-A.l a)was then isolated via column chromatography.

In analogy to the above procedure the compounds of formula l-A.1 aa summarized in the following table C can be prepared

Table C:

Compound _R 3a R ⁴ tR [min] m/z [M+H]V method Number H-NMR (400 MHz, CDCI3)

1-1 CHs 1 -CN-cC ₃ H ₄ 0.883 291 .3 1

I-2 C-C3H5 1 -CN-cC ₃ H ₄ 0.972 316.9 2

I-3 C-C3H5 CHF ₂ 2.634 302.1 2

I-4 C-C3H5 methoxy- 0.86 (m, 2H), 0.99 (m, 2H), 2.42 1

iminomethyl (s, 3H),

2.67 (m, 1 H), 4.02 (s, 3H), 4.76

(s, 2H), 7.28 (s, 1 H), 7.56 (s, 1 H),

7.80 (m, 1 H), 8.40 (m, 1 H)

I-5 C-C3H5 CH ₃ — 0.79 (m, 2H), 0.92 (m, 2H), 2.1 1 2 Compound _R 3a R ⁴ tR [min] m/z [M+H]V method Number H-NMR (400 MHz, CDC )

(s, 3H),

2.34 (s, 3H), 2.60 (m, 1 H), 4.67

(s, 2H), 7.28 (s, 1 H), 7.61 (m,

1 H), 8.35 (m, 1 H)

I-6 C-C3H5 CFs 3.050 320.1 2

C-C3H5: cyclopropyl

1 -CN-cC ₃ H _4: 1 -cyanocyclopropyl

3. Preparation of N-[1 -[(6-chloropyridyl-3-yl)methyl]-methylamino]ethyliden

thioacylamides (l-A.5aa) (compounds of the formula I, wherein Het is 6-chloropyridin-3-yl, R = R2 = H, R ^3b = CH ₃ and X is S)

Compounds of the formula l-A.5aa were prepared by treating a compound of formula (I-A.1 with P ₄ Sio-pyridine complex in acetonitrile at 80°C for 4 hours.

In analogy to the above procedure, the compound of formula l-A.5aa summarized in the following table D can be prepared

Table D

C-C3H5: cyclopropyl B Biological Examples

The biological activity of the compounds of formula I of the present invention may be evaluated in biological tests as described in the following. General conditions: If not otherwise specified, most test solutions are to be prepared as follows: The active compound is to be dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled watenacteon. Further, the test solutions are to be prepared at the day of use (and, if not otherwised specified, in general at concentrations wt/vol). B.1 Green Peach Aphid (Myzus pers/cae)

For evaluating control of green peach aphid (Myzus pers/cae) through systemic means, the test unit consists of 96-well-microtiter plates containing liquid artificial diet under an artificial membrane.

The compounds are formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds are pipetted into the aphid diet, using a custom built pipetter, at two replications.

After application, 5 - 8 adult aphids are placed on the artificial membrane inside the microtiter plate wells. The aphids are 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 is then visually assessed.

In this test, compound I-2 and I-4 at 2500 ppm showed at least 75 % mortality in comparison with untreated controls.

B.2 Vetch aphid (Megoura viciae)

For evaluating control of vetch aphid (Megoura viciae) through contact or systemic means the test unit consisted of 24-well-microtiter plates containing broad bean leaf disks.

The compounds were formulated using a solution containing 75% v/v water and 25% v/v

DMSO. Different concentrations of formulated compounds were sprayed onto the leaf disks at

2.5 μΙ, using a custom built micro atomizer, at two replications.

After application, the leaf disks were air-dried and 5 - 8 adult aphids were placed on the leaf disks inside the microtiter plate wells. The aphids were then allowed to suck on the treated leaf disks and were 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, compound I-4 and I-6 at 2500 ppm showed at least 75 % mortality in comparison with untreated controls.

B.3 Cowpea aphid (Aphis craccivora)

The active compound is dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water : acetone. Surfactant (Alkamuls® EL 620) is added at a rate of 0.1 % (vol/vol). The test solution is prepared at the day of use. Potted cowpea plants are colonized with approximately 50 - 100 aphids of various stages by manually transferring a leaf tissue cut from infested plant 24 hours before application. Plants are sprayed after the pest population has been recorded. Treated plants are maintained on light carts at about 28°C. Percent mortality is assessed after 72 hours.

In this test, compounds I-4 at 500 ppm showed at least 75 % mortality in comparison with untreated controls.

B.4 Cotton aphid {Aphis gossypil)

The active compound is dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water : acetone. Surfactant (Alkamuls® EL 620) is added at a rate of 0.1 % (vol/vol). The test solution is prepared at the day of use.

Potted cowpea plants are colonized with approximately 50 - 100 aphids of various stages by manually transferring a leaf tissue cut from infested plant 24 hours before application. Plants are sprayed after the pest population has been recorded. Treated plants are maintained on light carts at about 28°C. Percent mortality is assessed after 72 hours.

B.5 Orchid thrips (dichromothrips corbetti)

Dichromothrips corbetti a6u\\s used for bioassay are obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the test compound is diluted in a 1 :1 mixture of acetone:water (vohvol), plus 0.01 % vol/vol Alkamuls ^® EL 620 surfactant.

Thrips potency of each compound is evaluated by using a floral-immersion technique. Plastic petri dishes are used as test arenas. All petals of individual, intact orchid flowers are dipped into treatment solution and allowed to dry. Treated flowers are placed into individual petri dishes along with about 20 adult thrips. The petri dishes are then covered with lids. All test arenas are held under continuous light and a temperature of about 28°C for duration of the assay. After 3 days, the numbers of live thrips are counted on each flower, and along inner walls of each petri dish. The percent mortality is recorded 72 hours after treatment.

In this test, compounds I-3, I-4, I-5 and I-7 at 500 ppm showed at least 75 % mortality in comparison with untreated controls.

B.6 Rice green leafhopper (Nephotettix virescens)

Rice seedlings are cleaned and washed 24 hours before spraying. The active compounds are formulated in 50:50 acetone:water (vohvol), and 0.1 % vol/vol surfactant (EL 620) is added. Potted rice seedlings are sprayed with 5 ml test solution, air dried, placed in cages and inoculated with 10 adults. Treated rice plants are kept at about 28-29°C and relative humidity of about 50-60%. Percent mortality is recorded after 72 hours.

B.7 Rice brown plant hopper Nilaparvata lugens)

Rice seedlings are cleaned and washed 24 hours before spraying. The active compounds is formulated in 50:50 acetone:water (vohvol) and 0.1 % vol/vol surfactant (EL 620) was added. Potted rice seedlings are sprayed with 5 ml test solution, air dried, placed in cages and inoculated with 10 adults. Treated rice plants are kept at about 28-29°C and relative humidity of about 50-60%. Percent mortality is recorded after 72 hours.

B.8 Boll weevil {Anthonomus grandis)

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

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

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

B.9 Mediterranean fruitfly (Ceratitis capitata)

For evaluating control of Mediterranean fruitfly {Ceratitis capitata) the test unit consisted of microtiter plates containing an insect diet and 50-80 C. capitata eggs.

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

After application, microtiter plates were incubated at about 28 + 1 °C and about 80 + 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed.

B.10 Silverleaf whitefly {Bemisia argentifolii) (adults)

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 pla-ced 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. B.1 1 Green Soldier Stink Bug (Nezara viridula) The active compound is dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water : aceteone. Surfactant (Kinetic HV) is added at a rate of 0.01 % (vol/vol).The test solution is prepared at the day of use.

Soybean pods were placed in microwavable plastic cups lined with moist filter paper and inoculated with ten 3rd instar N. viridula. Using a hand atomizer, approximately 2 ml solution is sprayed into each cup. Treated cups were kept at about 28-29°C and relative humidity of about 50-60%. Percent mortality was recorded after 5 days.

B.12 Diamond back moth (Plutella xylostella)

The active compound is dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water : aceteone. Surfactant (Alkamuls® EL 620) is added at a rate of 0.1 %

(vol/vol). The test solution is prepared at the day of use.

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

B.13 Southern armyworm (Spodoptera eridania),

The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01 % (v/v).

Lima bean plants (variety Sieva) were grown 2 plants to a pot and selected for treatment at the 1 ^st true leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into perforated plastic bags with a zip closure. About 10 to 1 1 armyworm larvae were placed into the bag and the bags zipped closed. Test plants were maintained in a growth room at about 25°C and about 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the bags. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants.

B.14 Tobacco budworm {Heliothis virescens)

For evaluating control of tobacco budworm {Heliothis virescens) the test unit consisted of

96-well-microtiter plates containing an insect diet and 15-25 H. virescens eggs.

The compounds were formulated using a solution containing 75% v/v water and 25% v/v

DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at

10 μΙ, using a custom built micro atomizer, at two replications.

After application, microtiter plates were incubated at about 28 ± 1 °C and about 80 ± 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed.