Pyrazinothiazines Having Herbicidal Action

• US 20130012388A1
• Filed: 03/18/2011
• Published: 01/10/2013
• Est. Priority Date: 03/23/2010
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: BASF SE
• Inventors: Song, Dschun, Hutzler, Johannes, Newton, Trevor William, Witschel, Matthias, Moberg, William Karl, Parra Rapado, Liliana, Qu, Tao, Stelzer, Frank, Van Der Kloet, Andree, Seitz, Thomas, Ehrhardt, Thomas, Kreuz, Klaus, Grossmann, Klaus, Michrowska-Pianowska, Anna Aleksandra, Simon, Anja, Reingruber, Ruediger, Kraus, Helmut, Hoeffken, Hans Wolfgang, Mietzner, Thomas, Major, Julia
• Granted Patent: US 8,575,068 B2
• Time in Patent Office: Days
• US Class Current: 504/221
• CPC Class Codes: A01N 43/90 having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• CPC Class Codes: C07D 513/04 Ortho-condensed systems

Abstract

Substituted pyridazines of the formula I

in which the variables are defined according to the description, processes and intermediates for preparing the compounds of the formula I and their N oxides, their agriculturally useful salts, compositions comprising them and their use as herbicides, and also a method for controlling unwanted vegetation.

Claims

1-15. -15. (canceled)

16. A substituted pyridazine of the formula

17. The compound of the formula I according to claim 16 in which A is CR².

18. The compound of the formula I according to claim 17 in which

R² is an optionally substituted five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S.

19. The compound of the formula I according to claim 17 in which R² is

20. The compound of the formula I according to claim 18 in which R² is an optionally R^b-substituted heterocycle selected from the group consisting of isoxazoline, tetrazolone, 1,2-dihydrotetrazolone, 1,4-dihydrotetrazolone, tetrahydrofuran, dioxolane, piperidine, morpholine, piperazine, isoxazole, pyrazole, thiazole, oxazole, furyl, pyridine and pyrazine.

21. The compound of the formula I according to claim 17 in which

R² is an aliphatic group selected from the group consisting of C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, Z—

C₁-C₄-alkoxy, Z—

C₁-C₄-haloalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-haloalkenyloxy, C₃-C₆-haloalkynyloxy, C₁-C₄-alkoxy-carbonyl, S(O)_n—

C₁-C₈-alkyl and S(O)_n—

C₁-C₈-haloalkyl.

22. The compound of the formula I according to claim 16 in which

R¹ is halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio or C₁-C₄-alkylsulfonyl;

and

R³ is H, halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, or C₁-C₄-alkylsulfonyl.

23. The compound of the formula I according to claim 17 in which R² together with R¹ or R³ forms an optionally R^b-substituted five- to ten-membered mono- or bicyclic partially unsaturated ring which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S.

24. The compound of the formula I according to claim 23 in which the ring substituted by groups R¹, R², R³ and R⁴ corresponds to one of groups A to L

25. The compound of the formula I according to claim 16 in which A is nitrogen.

26. The compound of the formula I according to claim 25 in which

R¹ is nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio or C₁-C₄-alkylsulfonyl;

and

R³ is H, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio or C₁-C₄-alkylsulfonyl.

27. The compound of the formula I according to claim 16 in which the groups R^b are selected from the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₄-alkylthio-C₁-C₄-alkyl.

28. The compound of the formula I according to claim 16 in which

R^A is H, C₃-C₈-alkenyl, C₃-C₈-haloalkenyl, C₃-C₈-alkynyl, C₃-C₈-haloalkynyl or C₁-C₆-alkylcarbonyl;

R^x is C₁-C₆-alkyl or C₁-C₄-haloalkyl; and

R⁴, R⁵, R⁶ are H.

29. A composition comprising a herbicidally effective amount of at least one compound of the formula I or an agriculturally suitable salt thereof according to claim 16 and auxiliaries customary for formulating crop protection agents.

30. A method for controlling unwanted vegetation which comprises allowing a herbicidally effective amount of at least one compound of claim 16 to act on plants, their seed and/or their habitat.

31. The method of claim 30, wherein, in the compound of the formula I, A is CR².

32. The method of claim 31, wherein, in the compound of the formula I,

R² is an optionally substituted five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S.

33. The method of claim 31, wherein, in the compound of the formula I, R² is

34. The method of claim 32, wherein, in the compound of the formula I, R² is an optionally R^b-substituted heterocycle selected from the group consisting of isoxazoline, tetrazolone, 1,2-dihydrotetrazolone, 1,4-dihydrotetrazolone, tetrahydrofuran, dioxolane, piperidine, morpholine, piperazine, isoxazole, pyrazole, thiazole, oxazole, furyl, pyridine and pyrazine.

35. The method of claim 31, wherein, in the compound of the formula I,

R² is an aliphatic group selected from the group consisting of C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, Z—

C₁-C₄-alkoxy, Z—

C₁-C₄-haloalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-haloalkenyloxy, C₃-C₆-haloalkynyloxy, C₁-C₄-alkoxy-carbonyl, S(O)_n—

C₁-C₈-alkyl and S(O)_n—

C₁-C₈-haloalkyl.

36. The method of claim 30, wherein, in the compound of the formula I,

R¹ is halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio or C₁-C₄-alkylsulfonyl;

and

R³ is H, halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, haloalkoxy, C₁-C₄-alkylthio, or C₁-C₄-alkylsulfonyl.

37. The method of claim 31, wherein, in the compound of the formula I, R² together with R¹ or R³ forms an optionally R^b-substituted five- to ten-membered mono- or bicyclic partially unsaturated ring which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S.

38. The method of claim 37, wherein, in the compound of the formula I, the ring substituted by groups R¹, R², R³ and R⁴ corresponds to one of groups A to L

39. The method of claim 30, wherein, in the compound of the formula I, A is nitrogen.

40. The method of claim 39, wherein, in the compound of the formula I,

R¹ is nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio or C₁-C₄-alkylsulfonyl;

and

R³ is H, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio or C₁-C₄-alkylsulfonyl.

41. The method of claim 30, wherein, in the compound of the formula I, the groups R^b are selected from the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₄-alkylthio-C₁-C₄-alkyl.

42. The method of claim 30, wherein, in the compound of the formula I,

R^A is H, C₃-C₈-alkenyl, C₃-C₈-haloalkenyl, C₃-C₈-alkynyl, C₃-C₈-haloalkynyl or C₁-C₆-alkylcarbonyl;

R^x is C₁-C₆-alkyl or C₁-C₄-haloalkyl; and

R⁴, R⁵, R⁶ are H.