N-SUBSTITUTED IMINO HETEROCYCLIC COMPOUNDS

• US 20160326153A1
• Filed: 12/17/2014
• Published: 11/10/2016
• Est. Priority Date: 12/18/2013
• Status: Abandoned Application

• Current Assignee: BASF SE
• Original Assignee: BASF SE
• Inventors: KRBER, Karsten, MCLAUGHLIN, Martin John, GOCKEL, Birgit, VON DEYN, Wolfgang, DIETZ, Jochen, POHLMAN, Matthias
• Application Number:
  US15/105,239
• Publication Number:
  US 20160326153A1
• Time in Patent Office: Days
• US Class Current: 1/1
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/78 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• CPC Class Codes: A61P 33/00 Antiparasitic agents
• CPC Class Codes: C07D 213/76 to which a second hetero atom is attached nitro radicals C07D213/61
• CPC Class Codes: C07D 401/06 linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C07D 405/06 linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C07D 413/06 linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C07D 417/06 linked by a carbon chain containing only aliphatic carbon atoms

Abstract

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

wherein Y is a radical Y¹, Y², Y³, Y⁴ or Y⁵, where

• • Y¹ is O—C(═X)—R³;
  • Y² is S—C(═X)—R³;
  • Y³ is N(R⁵)—C(═X)—R³;
  • Y⁴ is N(R⁵)—S(═O)—R⁴;
  • Y⁵ is N(R⁵)—S(═O)₂—R⁴;
  • and where X is O or S;
• 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, C₁-C₆-alkyl etc.;
• and where R³, R⁴ and R⁵ are as defined herein.

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

1-25. -25. (canceled)

26. A compound of formula (I):

27. The compound of claim 26, wherein

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

28. The compound of claim 27, wherein

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

29. The compound of claim 28, wherein Het is Het-1a

30. The compound of claim 26, 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.

31. The compound of claim 30, wherein both R¹ and R² are hydrogen.

32. The compound of claim 26, where in the radicals Y¹ and Y³

R³ is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₆-cycloalkyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1, 2 or 3 radicals R⁷,

OR⁸, NR^18aR^18b, C(═

O)NR^9aR^9b, C(═

S)NR^9aR^9b, C(═

O)OR⁸, C(═

O)R^7a, C(═

S)R^7a, C(═

NR¹⁷)R^7d,

phenyl, which is unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 identical or different substituents R¹⁰,

and a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated or unsaturated 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 R¹⁰, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized.

33. The compound of claim 32, wherein

R³ is selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₂-C₄-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 R⁷,

OR⁸, NR^18aR^18b, C(═

NR¹⁷)R^7d,

phenyl, which is unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 identical or different substituents R¹⁰, and

a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated or unsaturated 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 R¹⁰, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, where, irrespectively of their occurrence,

R⁷ is selected from the group consisting of CN, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, S(O)_nR^8a, S(O)_nNR^17aR^17b, NR^17aR^17b, C(═

O)NR^17aR^17b, C(═

S)NR^17aR^17b, C(═

O)OR⁸, C(═

O)R¹⁵, NR^17a—

C(═

O)R^7a,

NR^17a—

C(═

O)OR^8a, NR^17a—

C(═

O)NR^17aR^17b, phenyl and phenoxy, where the phenyl ring in the last two mentioned radicals is unsubstituted or carriers 1, 2, 3, 4 or 5 radicals R¹⁰,

it being possible that R⁷ may also be C₁-C₄-alkyl or C₁-C₄-haloalkyl, if R³ is C₃-C₆-cycloalkyl;

R^7a is selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstituted or carries 1, 2, 3 or 4 radicals R¹⁰;

R^7d is selected from hydrogen, cyano, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstituted or carries 1, 2, 3 or 4 radicals R¹⁰;

R⁸ is selected from the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl, NH₂—

C(O), C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl, phenyl, benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or carries 1, 2, 3 or 4 radicals R¹⁰,

phenylcarbonyl, phenoxycarbonyl, wherein the last two radicals may be unsubstituted, partially or fully halogenated and/or may carry 1, 2 or 3 substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)amino and di-(C₁-C₆-alkyl)amino and

phenylaminocarbonyl, wherein the last mentioned radical may be unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆ haloalkoxy and (C₁-C₆-alkoxy)carbonyl;

R^8a is selected from the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl and phenyl, which is unsubstituted or carries 1, 2, 3 or 4 radicals R¹⁰;

R¹⁰ is selected from the group consisting of halogen, CN, OH, SH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl, NH₂—

C(O), C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulfonyl, SO₂NH₂, C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)aminocarbonyl;

R¹⁵ is selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and phenyl, which may be unsubstituted, partially or fully halogenated and/or may carry 1, 2 or 3 substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)amino and di-(C₁-C₆-alkyl)amino;

R¹⁷ is selected from C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₂-C₄-alkenyloxy and C₂-C₄-haloalkenyloxy;

R^17a, R^17b are each independently from one another selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, phenyl and benzyl, where the phenyl ring in the last two substituents may be unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆ haloalkoxy and (C₁-C₆-alkoxy)carbonyl;

R^18a, R^18b are each independently from one another selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₆-cycloalkyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1, 2 or 3 radicals R⁷,

C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl, NH₂—

C(O), C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl, NH₂—

S(O)₂, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylaminosulfonyl, di-(C₁-C₄-alkyl)aminosulfonyl,

phenyl, which is unsubstituted or carries 1, 2, 3 or 4 radicals R¹⁰ phenoxy, which may be unsubstituted, partially or fully halogenated and/or may carry 1, 2 or 3 substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆ haloalkoxy, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)amino or di-(C₁-C₆-alkyl)amino, and a 5- or 6-membered 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 R¹⁰,

or,

R^18a and R^18b are together 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 and nitrogen, and where the alkylene chain may optionally be substituted with 1, 2, 3 or 4 radicals selected from halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio and C₁-C₆-haloalkylthio.

34. The compound of claim 33, wherein R³ is a radical NR^18aR^18b.

35. The compound of claim 26, where in the radical Y³,

R⁵ if present, is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, wherein each of the four last mentioned radicals are unsubstituted, partly or completely halogenated,

C(═

O)OR⁸, C(═

O)R^7a, C(═

S)R^7a,

phenyl and phenyl-C₁-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 R¹⁰.

36. The compound of claim 35, wherein

R⁵ if present, is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, wherein each of the two last mentioned radicals are unsubstituted, partly or completely halogenated,

C(═

O)OR⁸, C(═

O)R^7a and C(═

S)R^7a,

where, irrespectively of their occurrence,

R^7a is selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstituted or carries 1, 2, 3 or 4 radicals R¹⁰;

R⁸ is selected from the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁i-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl, NH₂—

C(O), C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl, phenyl, benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or carries 1, 2, 3 or 4 radicals R¹⁰,

phenylcarbonyl, phenoxycarbonyl, wherein the last two radicals may be unsubstituted, partially or fully halogenated and/or may carry 1, 2 or 3 substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)amino or di-(C₁-C₆-alkyl)amino, and

phenylaminocarbonyl, wherein the last mentioned radical may be unsubstituted, partially or fully halogenated and/or may carries 1, 2 or 3 substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and (C₁-C₆-alkoxy)carbonyl.

37. The compound of claim 26, wherein the radical A is selected from the group consisting of W.Het-2, W.Het-6 and W.Het-10.

38. The compound of claim 37, wherein R^w5 is hydrogen.

39. The compound of claim 26, 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,

40. The compound of claim 26, wherein

Y is Y³

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, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₆-cycloalkyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1, 2 or 3 radicals R⁷,

OR⁸, NR^18aR^18b, C(═

O)NR^9aR^9b, C(═

S)NR^9aR^9b, C(═

O)OR⁸, C(═

O)R^7a, C(═

S)R^7a, C(═

NR¹⁷)R^7d,

phenyl, which is unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 identical or different substituents R¹⁰,

and a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated or unsaturated 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 R¹⁰, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,

R⁵ is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, wherein each of the four last mentioned radicals are unsubstituted, partly or completely halogenated, C(═

O)OR⁸, C(═

O)R^7a, C(═

S)R^7a,

phenyl and phenyl-C₁-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 R¹⁰,

or

R³ and R⁵ together form a bivalent radical, selected from the group consisting of C₃-C₆-alkanediyl, C₄-C₆-alkenediyl, S—

C₂-C₄-alkanediyl-S and S—

C₂-C₄-alkenediyl-S, wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1, 2, 3 or 4 radicals R^7b.

41. The compound of claim 40, wherein

both R¹ and R² are hydrogen;

R³ is selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₂-C₄-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 R⁷,

OR⁸, NR^18aR^18b, C(═

NR¹⁷)R^7d,

phenyl, which is unsubstituted or optionally substituted with 1, 2, 3, 4 or 5 identical or different substituents R¹⁰, and

a 3-, 4-, 5-, 6- or 7-membered saturated, partly saturated or unsaturated 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 R¹⁰, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, where, irrespectively of their occurrence,

R⁵ if present, is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, wherein each of the three last mentioned radicals are unsubstituted, partly or completely halogenated, C(═

O)OR⁸, C(═

O)R^7a, C(═

S)R^7a,

R³ and R⁵ together form a bivalent radical, selected from the group consisting of C₃-C₆-alkanediyl, C₄-C₆-alkenediyl, S—

C₂-C₄-alkanediyl-S and S—

C₂-C₄-alkenediyl-S, wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1, 2, 3 or 4 radicals R^7b, which are selected from methyl and halogen,

where, irrespectively of their occurrence,

R⁷ is selected from the group consisting of CN, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, S(O)_nR^8a, S(O)_nNR^17aR^17b, NR^17aR^17b, C(═

O)NR^17aR^17b, C(═

S)NR^17aR^17b, C(═

O)OR⁸, C(═

O)R¹⁵, NR^17a—

C(═

O)R^7aNR^17a—

C(═

O)OR^8a, NR^17a—

C(═

O)NR^17aR^17b, phenyl and phenoxy, where the phenyl ring in the last two mentioned radicals is unsubstituted or carriers 1, 2, 3, 4 or 5 radicals R¹⁰,

it being possible that R⁷ may also be C₁-C₄-alkyl or C₁-C₄-haloalkyl, if R³ is C₃-C₆-cycloalkyl;

R^7a is selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstituted or carries 1, 2, 3 or 4 radicals R¹⁰;

R^7d is selected from hydrogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstituted or carries 1, 2, 3 or 4 radicals R¹⁰;

R⁸ is selected from the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl, NH₂—

C(O), C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl, phenyl, benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or carries 1, 2, 3 or 4 radicals R¹⁰,

phenylcarbonyl, phenoxycarbonyl, wherein the last two radicals may be unsubstituted, partially or fully halogenated and/or may carry 1, 2 or 3 substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)amino and di-(C₁-C₆-alkyl)amino, and

phenylaminocarbonyl, which may be unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆ haloalkoxy and (C₁-C₆-alkoxy)carbonyl;

R^8a is selected from the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl and phenyl, which is unsubstituted or carries 1, 2, 3 or 4 radicals R¹⁰;

R¹⁰ is selected from the group consisting of halogen, CN, OH, SH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl, NH₂—

C(O), C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulfonyl, SO₂NH₂, C₁-C₄-alkylaminocarbonyl and, di-(C₁-C₄-alkyl)aminocarbonyl;

R¹⁵ is selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and phenyl, which is unsubstituted or carries 1, 2 3 or 4 radicals R¹⁰;

R¹⁷ is selected from C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₂-C₄-alkenyloxy and C₂-C₄-haloalkenyloxy;

R^17a, R^17b are each independently from one another selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, phenyl and benzyl, where the phenyl ring in the last two substituents may be unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆ haloalkoxy and (C₁-C₆-alkoxy)carbonyl;

R^18a, R^18b are each independently from one another selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₆-cycloalkyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1, 2 or 3 radicals R⁷,

C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl, NH₂—

C(O), C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl, NH₂—

S(O)₂, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylaminosulfonyl, di-(C₁-C₄-alkyl)aminosulfonyl,

phenyl, which is unsubstituted or carry 1, 2 3 or 4 radicals R¹⁰, phenoxy, which may be unsubstituted, partially or fully halogenated and/or may carry 1, 2 or 3 substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆ haloalkoxy, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)amino and di-(C₁-C₆-alkyl)amino;

and a 5- or 6-membered 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 R¹⁰,

or,

R^18a and R^18b are together 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 and nitrogen, and where the alkylene chain may optionally be substituted with 1, 2, 3 or 4 radicals selected from halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁i-C₆-haloalkoxy, C₁-C₆-alkylthio and C₁-C₆-haloalkylthio.

42. The compound of claim 40, wherein R³ is a radical NR^18aR^18b.

43. The compound of claim 26, wherein

X is O.

44. An agricultural or veterinary composition for combating animal pests comprising at least one compound as defined in claim 26 and at least one inert liquid and/or solid acceptable carrier and optionally, if desired, at least one surfactant.

45. 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 26.

46. 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 26.

47. A method for the protection of plant propagation material, especially seeds, 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 26.

48. 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 26.