N-ACYLIMINO HETEROCYCLIC COMPOUNDS

• US 20160297793A1
• Filed: 11/21/2014
• Published: 10/13/2016
• Est. Priority Date: 11/22/2013
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: BASF SE
• Inventors: MCLAUGHLIN, Martin John, GOCKEL, Birgit, BANDUR, Nina Gertrud, DIETZ, Jochen, POHLMAN, Matthias, Krber, Karsten, VON DEYN, Wolfgang
• Granted Patent: US 9,783,523 B2
• Time in Patent Office: Days
• US Class Current: 1/1
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/60 1,4-Diazines; Hydrogenated 1,4-diazines
• CPC Class Codes: A01N 43/78 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• CPC Class Codes: A01N 43/80 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• CPC Class Codes: A01N 43/84 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
• CPC Class Codes: A01N 47/10 Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
• CPC Class Codes: A61P 33/00 Antiparasitic agents
• CPC Class Codes: C07D 401/06 linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C07D 401/14 containing three or more hetero rings
• CPC Class Codes: C07D 405/06 linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C07D 409/14 containing three or more hetero rings
• CPC Class Codes: C07D 413/14 containing three or more hetero rings
• CPC Class Codes: C07D 417/06 linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C07D 417/14 containing three or more hetero rings
• CPC Class Codes: C07D 419/14 containing three or more hetero rings

Abstract

The present invention relates to N-acylimino compound of formula (I):

wherein X is O or S, in particular O;

• Y is a single bond, O, S or NR⁵;
• Het is a 5 or 6 membered carbon-bound or nitrogen-bound heterocyclic ring,
• W¹—W²—W³—W⁴ represents a carbon chain group connected to N and C═N, and thus forming a saturated, unsaturated, or partially unsaturated 5 or 6 membered nitrogen containing heterocycle, wherein W¹, W², W³ and W⁴ each individually represent CR^vR^w;
• R¹, R² may be hydrogen, halogen, etc.;
• R³ may be hydrogen, CN, C₁-C₆-alkyl, etc.;
• R⁴ may be of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₃-C₈-cycloalkyl, Q-phenyl, Q′-O-phenyl, Q′-S-phenyl, where the phenyl ring is optionally substituted with one or more, e.g. 1, 2, 3, 4 or 5 identical or different substituents R¹⁰, and the moieties Q-Het^#, Q′-O-Het^# and Q′-S-Het^# where Het# represents a heterocyclic radical and where Q and Q′ are C1-C6-alkandiyl, C2-C6-alkendiyl, or C2-C6-alkyndiyl, and where Q may also be a single bond;
• R³ and R⁴ together may also may also a bivalent radical, selected from the group consisting of C₂-C₅-alkandiyl, C₂-C₅-alkendiyl, Q″-C₁-C₄-alkandiyl and Q″-C₂-C₄-alkendiyl, where Q″ is O or S.

The invention also relates to the use of the N-acylimino heterocyclic compounds, 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 compounds.

Claims

1-38. -38. (canceled)

39. An N-acylimino compound of formula (I):

40. The compound of claim 39, wherein

Het is selected from the group consisting of radicals of the following formula Het-1 to Het-24:

41. The compound of claim 40, wherein

Het is selected from the group consisting of radicals of formulae Het-1, Het-11a and Het-24,

42. The compound of claim 41, wherein Het is Het-1a

43. The compound of claim 39, wherein

R¹, R² are independently from each other selected from the group consisting of hydrogen, halogen, CN, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₃-C₆-halocycloalkyl;

 

or

 

R¹ and R² may together be ═

CR¹³R¹⁴;

 

or

R¹ and R² form, together with the carbon atom, which they attached to, a 3- to 5-membered saturated carbocyclic ring.

44. The compound of claim 43, wherein both R¹ and R² are hydrogen.

45. The compound of claim 39, wherein

R³ is selected from the group consisting of hydrogen, NO₂, CN, C₁-C₆-alkyl, C₁i-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₆-alkynyl, which is unsubstituted, partly or completely halogenated or carries a radical R^7d;

 

OR⁸, NR^9aR^9b, C(═

O)OR⁸, C(═

O)NR^9aR^9b, C(═

NOR²¹)OR⁸, C(═

NOR²¹)NR^9aR^9b, C(═

S)NR^9aR^9b, C(═

O)R^7a, C(═

S)R^7a, and C(═

NOR²²)R^7a, where

R^7a is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl, pyridyl, pyridylmethyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,

 

C₁-C₆-alkyl, which is substituted by 1 or 2 radicals selected from phenyl, pyridyl, OR¹⁶, S(O)_nR¹⁶, S(O)_nNR^17aR^17b, NR^17aR^17b, C(═

O)NR^17aR^17b, C(═

O)OR¹⁶,

R^7d is selected from the group consisting of C₃-C₆-cycloalkyl, trimethylsilyl, phenyl, pyridyl and, it being possible for the last three mentioned groups to be unsubstituted, partly or completely halogenated,

R⁸ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, it being possible for the last three mentioned groups to be unsubstituted, partly or completely halogenated,

 

C₁-C₄-alkyl, which is substituted by 1 or 2 radicals selected from the group consisting of cyano, nitro, OR¹⁶, NR^17aR^17b, C(═

O)R¹⁵, C(═

O)OR¹⁶, C(═

O)NR^17aR^17b, C(═

S)NR^17aR^17b, phenyl and pyridyl, where the last two radicals are unsubstituted or carry 1, 2, 3 or 4 radicals selected from halogen,

R^9a, R^9b is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last two mentioned groups to be unsubstituted, partly or completely halogenated, one of R^9a, R^9b may also be C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkylmethoxy,

 

or R^9a together with R^9b forms a C₄-C₆ alkylene chain and form a 5-, 6- or 7-membered saturated, 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 and C₁-C₄-alkyl;

R¹⁵ is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl, pyridyl, pyridylmethyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,

R¹⁶ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl and benzyl, it being possible for the last four mentioned groups to be unsubstituted, partly or completely halogenated,

R¹⁷ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,

R^17a, R^17b is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, or R^17a together with R^17b forms a C₄-C₆ alkylene chain and form a 5-, 6- or 7-membered saturated, 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 and C₁-C₄-alkyl;

R²¹ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated;

R²² is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, it being possible for the last three mentioned groups to be unsubstituted, partly or completely halogenated

 

C₁-C₆-alkyl, which is substituted by 1 or 2 radicals selected from phenyl, pyridyl, OR⁸, S(O)_nR⁸, S(O)_nNR^17aR^17b, NR^17aR^17b, C(═

O)NR^17aR^17b, C(═

O)OR⁸,

 

phenyl and pyridyl, it being possible for phenyl and pyridiyl to be unsubstituted, partly or completely halogenated and/or carry 1, 2 or 3 substituents selected from halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆ haloalkoxy and (C₁-C₆-alkoxy)carbonyl.

46. The compound of claim 45, wherein

R³ is selected from the group consisting of hydrogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₃-C₄-cycloalkyl, C(═

O)R^7a, C(═

O)OR⁸, C(═

O)NR^9aR^9b, C(═

NOR²²)R^7a, and

 

ethynyl, which is unsubstituted or carries a radical selected from C₁-C₄-alkyl, C₁-C₂-haloalkyl, phenyl, C₃-C₆-cycloalkyl and trimethylsilyl;

 

where

R^7a is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, C₁-C₆-alkyl, which is substituted by 1 radical selected from phenyl, pyridyl, cyano, C₁-C₄-alkoxy, C₁-C₄-alkoxycarbonyl and C₃-C₄-cycloalkyl,

R⁸ is selected from the group consisting of C₁-C₄-alkyl, C₃-C₄-cycloalkyl, C₃-C₄-cycloalkylmethyl, benzyl and pyridylmethyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,

 

C₁-C₄-alkyl, which is substituted by 1 or 2 radicals selected from the group consisting of cyano, C₁-C₄-alkoxy, C₁-C₄-alkylamino and di-C₁-C₄-alkylamino,

R^9a, R^9b are selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₃-C₄-cycloalkyl, and C₃-C₄-cycloalkylmethyl, one of R^9a, R^9b may also be C₁-C₄-alkoxy, C₃-C₄-cycloalkoxy or C₃-C₆-cycloalkylmethoxy,

R²² is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, it being possible for the last three mentioned groups to be unsubstituted, partly or completely halogenated

 

C₁-C₄-alkyl, which is substituted by 1 or 2 radicals selected from phenyl, pyridyl, OR⁸, S(O)_nR⁸, NR^17aR^17b, C(═

O)NR^17aR^17b, C(═

O)OR⁸.

47. The compound of claim 45, wherein

R³ is hydrogen.

48. The compound of claim 45, wherein

R³ is selected from the group consisting of NO₂, CN, C(═

O)R^7a, C(═

O)OR⁸, C(═

O)NR^9aR^9b, and C(═

NOR²²)R^7a.

49. The compound of claim 45, wherein

R³ is selected from the group consisting of C₁-C₆-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl and

 

ethynyl, which is unsubstituted or carries a radical selected from C₁-C₄-alkyl, C₁-C₂-haloalkyl, phenyl, C₃-C₆-cycloalkyl and trimethylsilyl.

50. The compound of claim 45, wherein

R³ is selected from the group consisting of hydrogen, methyl, trifluoromethyl and CN.

51. The compounds of claim 39, wherein Y is O or S and

R⁴ is selected from the group consisting of

 

hydrogen, C₁-C₆-alkyl, which is unsubstituted, partially or completely halogenated or substituted by one radical selected from CN, C₃-C₆ cycloalkyl, OR⁸, S(O)_nR⁸, S(O)_nNR^17aR^17b, NR^17aR^17b, C(═

O)NR^17aR^17b, C(═

S)NR^17aR^17b, C(═

O)OR, C(═

O)R¹⁵, C(═

S)R¹⁵, C(═

NR¹⁷)R¹⁵, NR^17a—

C(═

S)R^7a, NR^17a—

C(═

O)OR⁸, NR^17a—

C(═

O)NR^17aR^17b, and 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring comprising 1, 2 or 3 heteroatoms as ring members, which are selected from oxygen, nitrogen and/or sulfur, where

R^7a is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,

R⁸ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl and benzyl, it being possible for the last four mentioned groups to be unsubstituted, partly or completely halogenated,

R¹⁵ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,

R¹⁷ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,

R^17a, R^17b is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, or R^17a together with R^17b forms a C₄-C₆ alkylene chain and form a 5-, 6- or 7-membered saturated, 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 and C₁-C₄-alkyl;

C₂-C₁₀-alkenyl, C₂-C₆ haloalkenyl, C₂-C₁₀-alkynyl, C₂-C₆ haloalkynyl,

C₃-C₆ cycloalkyl, which is unsubstituted, partially or completely halogenated and/or carry 1, 2, 3, 4, 5 or 6 C₁-C₄-alkyl groups,

the moieties Q-phenyl, Q′

-S-phenyl and Q′

-O-phenyl, where the phenyl ring is optionally substituted with 1, 2, 3, 4 or 5 identical or different substituents R¹⁰,

and the moieties Q-Het^# and Q′

-O-Het^# where

Het^# represents a 5- or 6-membered saturated, partially unsaturated or unsaturated aromatic heterocyclic ring comprising 1, 2 or 3 heteroatoms as ring members, which are selected from oxygen, nitrogen and/or sulfur, where the heterocyclic ring is optionally substituted with 1, 2, 3 or 4 identical or different substituents R¹⁰, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,

Q irrespectively of its occurrence, is a single bond, C₁-C₄-alkandiyl or C₃-C₄-alkendiyl;

Q′

irrespectively of its occurrence, is C₁-C₄-alkandiyl or C₃-C₄-alkendiyl;

or

R³ and R⁴ together may also a bivalent radical, selected from the group consisting of Q″

-C₁-C₄-alkandiyl and Q″

-C₂-C₄-alkendiyl, wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1, 2, 3 or 4 radicals R^7c, and wherein Q″

is selected from O and S and bound to the carbon atom, which carries R³,

where R¹⁰, irrespectively of its occurrence, is selected from halogen, CN, C₁-C₄-alkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, and C₁-C₄-haloalkoxy.

52. The compound of claim 50, wherein Y is O

R⁴ is selected from the group consisting of

C₁-C₆-alkyl, which is unsubstituted, partially or completely halogenated or substituted by one radical selected from CN, C₃-C₆ cycloalkyl, OR⁸, S(O)_nR⁸, S(O)_nNR^17aR^17b, C(═

O)NR^17aR^17b, C(═

S)NR^17aR^17b, C(═

O)OR⁸, NR^17a—

C(═

S)R^7a, NR^17a—

C(═

O)OR⁸, NR^17a—

C(═

O)NR^17aR^17b, and 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring comprising 1, 2 or 3 heteroatoms as ring members, which are selected from oxygen, nitrogen and/or sulfur,

R^7a is C₁-C₄-alkyl or C₁-C₄-haloalkyl,

R⁸ is C₁-C₄-alkyl or C₁-C₄-haloalkyl,

R^17a, R^17b are, independently of each other, selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and phenyl, which is unsubstituted, partly or completely halogenated;

C₃-C₆ cycloalkyl, which is unsubstituted, partially or completely halogenated and/or carry 1, 2, 3, 4, 5 or 6 C₁-C₄-alkyl groups,

C₂-C₁₀-alkenyl, C₂-C₆ haloalkenyl,

the moieties phenyl and benzyl, where the phenyl ring is optionally substituted with 1, 2, 3, 4 or 5 identical or different substituents R¹⁰,

the moieties Het^# and CH₂-Het^#, where

Het^# represents a 5- or 6-membered saturated, partially unsaturated or unsaturated aromatic heterocyclic ring comprising 1, 2 or 3 heteroatoms as ring members, which are selected from oxygen, nitrogen and/or sulfur, where the heterocyclic ring is optionally substituted with 1, 2 or 3 identical or different substituents R¹⁰,

or

R³ and R⁴ together may also a bivalent radical O—

CH₂CH₂, wherein 1, 2, 3 or 4 hydrogen atoms of CH₂CH₂ may be replaced by R^7c,

where R¹⁰, irrespectively of its occurrence, is selected from halogen, CN, C₁-C₄-alkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, and C₁-C₄-haloalkoxy.

53. The compound of claim 51, wherein R⁴ is CH₂-phenyl, CH₂-pyridyl or CH₂-thienyl, where phenyl, pyridyl and thienyl are unsubstituted or carry 1, 2 or 3 identical or different substituents R¹⁰, where R¹⁰ is selected from halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, and C₁-C₄-haloalkoxy.

54. The compound of claim 51, wherein R⁴ is

C₁-C₆-alkyl, which is unsubstituted, partially or completely halogenated or substituted by one radical selected from CN, C₃-C₆ cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-alkoxycarbonyl, and C₃-C₆ cycloalkyl, which is unsubstituted, partly or completely halogenated.

55. The compound of claim 51, wherein R⁴ is C₂-C₁₀-alkenyl, or C₂-C₆-haloalkenyl.

56. The compound of claim 51, wherein Y is O,

R³ is selected from the group consisting of hydrogen, methyl, trifluoromethyl and CN;

and

R⁴ is selected from the group consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl and C₂-C₆-haloalkenyl.

57. The compounds of claim 39, wherein

Y is N—

R⁵;

R⁴ is selected from the group consisting of

hydrogen, C₁-C₆-alkyl, which is unsubstituted, partially or completely halogenated or substituted by one radical selected from CN, C₃-C₆ cycloalkyl, OR⁸, S(O)_nR⁸, S(O)₁NR^17aR^17b, NR^17aR^17b, C(═

O)NR^17aR^17b, C(═

S)NR^17aR^17b, C(═

O)OR⁸, C(═

O)R¹⁵, C(═

S)R¹⁵, C(═

NR¹⁷)R¹⁵, NR^17a—

C(═

O)R^7a, NR^17a—

C(═

S)R^7a, NR^17a—

C(═

O)OR⁸,

NR^17a—

C(═

O)NR^17aR^17b, and 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring comprising 1, 2 or 3 heteroatoms as ring members, which are selected from oxygen, nitrogen and/or sulfur, where

R^7a is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,

R⁸ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl and benzyl, it being possible for the last four mentioned groups to be unsubstituted, partly or completely halogenated,

R¹⁵ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,

R¹⁷ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,

R^17a, R^17b is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, or R^17a together with R^17b forms a C₄-C₆ alkylene chain and form a 5-, 6- or 7-membered saturated, 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 and C₁-C₄-alkyl;

C₂-C₆-alkenyl, C₂-C₆ haloalkenyl, C₂-C₆-alkynyl, C₂-C₆ haloalkynyl,

C₃-C₆ cycloalkyl, which is unsubstituted, partially or completely halogenated and/or carry 1, 2, 3, 4, 5 or 6 C₁-C₄-alkyl groups,

C(═

O)OR¹⁸, C(═

O)NR^19aR^19b, C(═

S)NR^19aR^19b, C(═

O)R²⁰ or C(═

S)R²⁰, where

R¹⁸ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl and benzyl, it being possible for the last four mentioned groups to be unsubstituted, partly or completely halogenated,

R^19a, R^19b is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, or R^19a together with R^19b forms a C₄-C₆ alkylene chain and form a 5-, 6- or 7-membered saturated, 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 and C₁-C₄-alkyl;

R²⁰ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,

the moieties Q-phenyl and Q′

-O-phenyl, where the phenyl ring is optionally substituted with 1, 2, 3, 4 or 5 identical or different substituents R¹⁰,

and the moieties Q-Het^# and Q′

-O-Het^# where

Het^# represents a 5- or 6-membered aromatic heterocyclic ring comprising 1, 2 or 3 heteroatoms as ring members, which are selected from oxygen, nitrogen and/or sulfur, where the aromatic heterocyclic ring is optionally substituted with 1, 2, 3 or 4 identical or different substituents R¹⁰, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, and

Q irrespectively of its occurrence, is a single bond, C₁-C₄-alkandiyl or C₃-C₄-alkendiyl;

Q′

irrespectively of its occurrence, is C₁-C₄-alkandiyl or C₃-C₄-alkendiyl.

R⁵ is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₅-cycloalkyl, wherein each of the two last mentioned radicals are unsubstituted, partly or completely halogenated,

 

phenyl, or benzyl, 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 R¹⁰,

where R¹⁰, irrespectively of its occurrence, is selected from halogen, CN, C₁-C₄-alkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, and C₁-C₄-haloalkoxy.

58. The compound of claim 57, wherein

R⁴ is selected from the group consisting of

C₁-C₆-alkyl, which is unsubstituted, partially or completely halogenated or substituted by one radical selected from CN, C₃-C₆ cycloalkyl, OR⁸, S(O)_nR⁸, S(O)₁NR^17aR^17b, C(═

O)NR^17aR^17b, C(═

S)NR^17aR^17b, C(═

O)OR⁸, and 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring comprising 1, 2 or 3 heteroatoms as ring members, which are selected from oxygen, nitrogen and/or sulfur,

R^7a is C₁-C₄-alkyl or C₁-C₄-haloalkyl,

R⁸ is C₁-C₄-alkyl or C₁-C₄-haloalkyl,

R^17a, R^17b is selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and phenyl, which is unsubstituted, partly or completely halogenated;

C₃-C₆ cycloalkyl, which is unsubstituted, partially or completely halogenated and/or carry 1, 2, 3, 4, 5 or 6 C₁-C₄-alkyl groups,

C₂-C₁₀-alkenyl, C₂-C₆-haloalkenyl,

C(═

O)NR^19aR^19b, C(═

S)NR^19aR^19b, where

R^19a, R^19b is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated;

the moieties phenyl and benzyl, where the phenyl ring is optionally substituted with 1, 2, 3, 4 or 5 identical or different substituents R¹⁰,

the moieties Het^# and CH₂-Het^#, where

Het^# represents a 5- or 6-membered saturated, partially unsaturated or unsaturated aromatic heterocyclic ring comprising 1, 2 or 3 heteroatoms as ring members, which are selected from oxygen, nitrogen and/or sulfur, where the aromatic heterocyclic ring is optionally substituted with 1, 2 or 3 identical or different substituents R¹⁰;

R⁵ is selected from the group consisting of hydrogen and C₁-C₆-alkyl;

where R¹⁰, irrespectively of its occurrence, is selected from halogen, CN, C₁-C₄-alkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, and C₁-C₄-haloalkoxy.

60. The compound of claim 39, which is a compound of formula I-A

61. The compounds of claim 39, wherein the moiety of the formula

62. The compound of claim 61, wherein the radical A is selected from the group consisting of W.Het-2, W.Het-6 and W.Het-10.

63. The compound of claim 62, wherein R^w5 is hydrogen.

64. The compound of claim 61, wherein the radical A is selected from the group consisting of W.Het-2, W.Het-6 and W.Het-10 and wherein Het is selected from the group consisting of radicals of formulae Het-1, Het-11a and Het-24,

65. The compound of claim 61, wherein

R¹, R² are independently from each other selected from the group consisting of

hydrogen, halogen, CN, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-halocycloalkyl;

or

R¹ and R² may together be ═

CR¹³R¹⁴;

or

R¹ and R² form, together with the carbon atom, which they attached to, a 3- to 5-membered saturated carbocyclic ring; and

R³ is selected from the group consisting of hydrogen, NO₂, CN, C₁-C₆-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₆-alkynyl, which is unsubstituted, partly or completely halogenated or carries a radical R^7d;

OR⁸, NR^9aR^9b, C(═

O)OR⁸, C(═

O)NR^9aR^9b, C(═

NOR²¹)OR⁸, C(═

NOR²¹)NR^9aR^9b, C(═

S)NR^9aR^9b, C(═

O)R^7a, C(═

S)R^7a, and C(═

NOR²²)R^7a, where

R^7a is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl, pyridyl, pyridylmethyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,

 

C₁-C₆-alkyl, which is substituted by 1 or 2 radicals selected from phenyl, pyridyl, OR¹⁶, S(O)_nR¹⁶, S(O)_nNR^17aR^17b, NR^17aR^17b, C(═

O)NR^17aR^17b, C(═

O)OR¹⁶,

R^7d is selected from the group consisting of C₃-C₆-cycloalkyl, trimethylsilyl, phenyl, pyridyl and, it being possible for the last three mentioned groups to be unsubstituted, partly or completely halogenated,

R⁸ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, it being possible for the last three mentioned groups to be unsubstituted, partly or completely halogenated,

 

C₁-C₄-alkyl, which is substituted by 1 or 2 radicals selected from the group consisting of cyano, nitro, OR¹⁶, NR^17aR^17b, C(═

O)R¹⁵, C(═

O)OR¹⁶, C(═

O)NR^17aR^17b, C(═

S)NR^17aR^17b, phenyl and pyridyl, where the last two radicals are unsubstituted or carry 1, 2, 3 or 4 radicals selected from halogen,

R^9a, R^9b is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last two mentioned groups to be unsubstituted, partly or completely halogenated, one of R^9a, R^9b may also be C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkylmethoxy,

 

or R^9a together with R^9b forms a C₄-C₆ alkylene chain and form a 5-, 6- or 7-membered saturated, 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 and C₁-C₄-alkyl;

R¹⁵ is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl, pyridyl, pyridylmethyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,

R¹⁶ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl and benzyl, it being possible for the last four mentioned groups to be unsubstituted, partly or completely halogenated,

R¹⁷ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated,

R^17a, R^17b is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated, or R^17a together with R^17b forms a C₄-C₆ alkylene chain and form a 5-, 6- or 7-membered saturated, 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 and C₁-C₄-alkyl;

R²¹ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, phenyl and benzyl, it being possible for the last five mentioned groups to be unsubstituted, partly or completely halogenated;

R²² is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylmethyl, it being possible for the last three mentioned groups to be unsubstituted, partly or completely halogenated

 

C₁-C₆-alkyl, which is substituted by 1 or 2 radicals selected from phenyl, pyridyl, OR⁸, S(O)_nR⁸, S(O)_nNR^17aR^17b, NR^17aR^17b, C(═

O)NR^17aR^17b, C(═

O)OR⁸,

 

phenyl and pyridyl, it being possible for phenyl and pyridiyl to be unsubstituted, partly or completely halogenated and/or carry 1, 2 or 3 substituents selected from halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆ haloalkoxy and (C₁-C₆-alkoxy)carbonyl.

66. The compound of claim 61, wherein

both R¹ and R² are hydrogen;

and

R³ is hydrogen, NO₂, CN, C(═

O)R^7a, C(═

O)OR⁸, C(═

O)NR^9aR^9b, C(═

NOR²²)R^7a, C₁-C₆-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, and ethynyl, which is unsubstituted or carries a radical selected from C₁-C₄-alkyl, C₁-C₂-haloalkyl, phenyl, C₃-C₆-cycloalkyl and trimethylsilyl.

67. The compound of claim 61, wherein the radical A is W.Het-2, wherein R^w5 is hydrogen,

Y is O,

both R¹ and R² are hydrogen,

R³ is selected from the group consisting of hydrogen, methyl, trifluoromethyl and CN;

and

R⁴ is selected from the group consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl and C₂-C₆-haloalkenyl.

68. The compound of claim 67, wherein Het, X, R³ and R⁴ are as defined in one of rows 1 to 64 of the following table:

69. The compound of claim 39, wherein

X is O.

70. An agricultural or veterinary composition for combating animal pests comprising at least one compound as defined in claim 39 and at least one inert liquid and/or solid acceptable carrier and optionally, if desired, at least one surfactant.

71. 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 as defined in claim 39.

72. 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 as defined in claim 39.

73. A method for the protection of plant propagation material from soil insects and of the seedlings roots and shoots from soil and foliar insects comprising contacting the plant propagation material before sowing and/or after pregermination with at least one compound as defined in claim 39.

74. 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 as defined in claim 39.

75. The compound as defined in claim 39 for the use in the treatment 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.