Delta1-pyrrolines and their use as pest control agents

• US 20050124497A1
• Filed: 01/21/2003
• Published: 06/09/2005
• Est. Priority Date: 02/01/2002
• Status: Abandoned Application

• Current Assignee: Bayer Cropscience AG (Bayer AG)
• Original Assignee: Bayer Cropscience AG (Bayer AG)
• Inventors: Erdelen, Christoph, Seitz, Thomas, Lubos-Erdelen, Angelika, Fusslein, Martin, Turberg, Andreas, Jansen, Johannes Rudolf, Hansen, Olaf, Kraatz, Udo
• Application Number:
  US10/502,665
• Publication Number:
  US 20050124497A1
• Time in Patent Office: Days
• US Class Current: 504/246
• CPC Class Codes: A01N 43/74 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
• CPC Class Codes: C07D 207/20 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 413/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 417/10 linked by a carbon chain containing aromatic rings

Abstract

The present invention related to novel Δ¹-pyrrolines of the formula (I) in which

• • R¹, R², R³, R⁴, R⁵, R⁶ , X, Y, R⁷, R⁸ and R⁹ are as defined in the description disclosure. to a plurality of precesses for preparing these substances and their use for controlling pests, and to novel intermediates and processes for their preparation.

Claims

1-18. -18. (canceled)

19. A Δ

¹-pyrroline of formula (I)

20. A Δ

¹-pyrroline of formula (I) according to claim 19 in which

R¹ represents fluorine, chlorine, bromine, or methyl,

R² represents hydrogen, fluorine, or chlorine,

R³, R⁴, R⁵, and R⁶ independently of one another represent hydrogen, fluorine, chlorine, bromine, C₁-C₄-alkyl, or C₁-C₄-alkoxy,

X represents O or S,

Y represents CR¹⁰ or N,

R⁷, R⁸, R⁹, and R¹⁰ independently of one another represent hydrogen, fluorine, chlorine, bromine, nitro, C₁-C₄-alkyl;

represent C₁-C₄-haloalkyl, C₁-C₄-halo-alkoxy, or C₁-C₄-haloalkylthio having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms;

or represent C₁-C₄-alkoxycarbonyl, phenyl, —

(CH₂)_m—

SO₂R¹¹, or —

SO₂NR¹²R¹³,

or R⁷ and R⁸ together or R⁸ and R⁹ together or R⁹ and R¹⁰ together form a saturated or unsaturated 5- or 6-membered ring that optionally contains one or two heteroatom groupings selected from the group consisting of N, O, S, and SO₂,

m represents 0 or 1,

R¹¹ represents C₁-C₄-alkyl or morpholino,

R¹² represents C₁-C₄-alkyl or represents phenyl that is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, C₁-C₄-alkyl, and C₁-C₄-alkoxy, and R¹³ represents hydrogen or C₁-C₄-alkyl.

21. A Δ

¹-pyrroline of formula (I) according to claim 19 in which

R¹ represents fluorine, chlorine, or methyl,

R² represents hydrogen, fluorine, or chlorine,

R³ and R⁶ independently of one another represent hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, or ethoxy,

R⁴ and R⁵ each represent hydrogen,

X represents O or S,

Y represents CR¹⁰ or N,

R⁷, R⁸, R⁹, and R¹⁰ independently of one another represent hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl;

represent C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, or C₁-C₄-halo-alkylthio having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms;

or represent methoxycarbonyl, ethoxycarbonyl, phenyl, —

(CH₂)_m—

SO₂R¹¹ or —

SO₂NR¹²R¹³,

or R⁷ and R⁸ together or R⁸ and R⁹ together or R⁹ and R¹⁰ together form a saturated or unsaturated 5- or 6-membered ring that optionally contains one or two heteroatom groupings selected from the group consisting of N, O, S, and SO₂,

m represents 0 or 1,

R¹¹ represents methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, or morpholino,

R¹² represents methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, or t-butyl or represents phenyl that is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, and t-butoxy, and

R¹³ represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, or t-butyl.

22. A Δ

¹-pyrroline of formula (I) according to claim 19 in which

R¹ represents fluorine, chlorine, or methyl,

R² represents hydrogen, fluorine, or chlorine,

R³ represents hydrogen, fluorine, chlorine, methyl, methoxy, or ethoxy,

R⁴, R⁵, and R⁶ each represent hydrogen,

X represents O,

Y represents CR¹⁰ or N, and

R⁷, R⁸, R⁹, and R¹⁰ independently of one another represent hydrogen, fluorine, chlorine, bromine, nitro, methyl, i-propyl, t-butyl, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl, phenyl, —

SO₂-morpholino, —

CH₂SO₂Me, —

SO₂NHMe, —

SO₂NMe₂, —

SO₂NH-(3,4-dichlorophenyl), or —

SO₂NH-(2-methoxyphenyl).

23. A Δ

¹-pyrroline of formula (I) according to claim 19 in which R¹ and R² represent fluorine.

24. A Δ

¹-pyrroline of formula (I) according to claim 19 in which Y represents CR¹⁰.

25. A Δ

¹-pyrroline of formula (I) according to claim 24 in which R¹⁰ represents hydrogen.

26. A Δ

¹-pyrroline of formula (I) according to claim 19 in which R³ represents hydrogen or fluorine.

27. A Δ

¹-pyrroline of formula (I) according to claim 19 in which X represents O.

28. A Δ

¹-pyrroline of formula (I) according to claim 19 in which X represents S.

29. A Δ

¹-pyrroline of formula (I) according to claim 19 in which R⁴ and R⁵ represent hydrogen.

30. A Δ

¹-pyrroline of formula (I) according to claim 19 in which R¹ and R² represent fluorine, X represents O, and Y represents CH.

32. A process for preparing a compound of formula (I) according to claim 19 comprising reacting a compound of formula (II)

33. A pesticide comprising one or more compounds of formula (I) according to claim 19 and one or more extenders and/or surfactants.

34. A method for controlling pests comprising allowing an effective amount of a compound of formula (I) according to claim 19 to act on pests and/or their habitat.

35. A process for preparing a pesticides comprising mixing a compound of formula (I) according to claim 19 with one or more extenders and/or surfactants.

31. An (R)-configured compound of formula (I-a)

36. A compound of formula (II)