Novel 2-Cyano-3(Halo)Alkoxy-Benzenesulfonamide Compounds for Combating Animal Pests

• US 20080063678A1
• Filed: 11/24/2005
• Published: 03/13/2008
• Est. Priority Date: 11/26/2004
• Status: Active Grant

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Bastiaans, Henricus Maria, Anspaugh, Douglas, Cotter, Henry, Puhl, Michael, Tedeschi, Livio, Koradin, Christopher, Baumann, Ernst, Oloumi-Sadeghi, Hassan, Pohlman, Matthias, Hofmann, Michael, von Deyn, Wolfgang, Kordes, Markus, Rack, Michael, Culbertson, Deborah
• Granted Patent: US 7,544,637 B2
• Time in Patent Office: Days
• US Class Current: 424/405
• CPC Class Codes: A01N 41/06 Sulfonic acid amides
• CPC Class Codes: C07C 311/29 having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 319/20 by reactions not involving the formation of sulfide groups
• CPC Class Codes: C07C 323/62 having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton

Abstract

The invention relates to 2-cyano-3-(halo)alkoxy-benzenesulfonamide compounds I
where the variables Alk and R¹ to R⁵ are as defined in claim 1, and/or to their agriculturally useful salts. Moreover, the present invention relates to the use of compounds I and/or their salts for combating animal pests; agricultural compositions comprising such an amount of at least one compound of the general formula I and/or at least one agriculturally useful salt of I and at least one inert liquid and/or solid agronomically acceptable carrier that it has a pesticidal action and, if desired, at least one surfactant; and a method of combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, plant, 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 one2-cyano-3-(halo)alkoxy-benzenesulfonamide compound of the formula I and/or at least one agriculturally acceptable salt thereof. a method for the for the protection of seeds from soil insects and of the resulting plant'"'"'s roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermination with a 2-cyano-3-(halo)alkoxy-benzenesulfonamide compound of the general formula I

Claims

1-21. -21. (canceled)

22. A 2-cyano-3-(halo)alkoxy-benzenesulfonamide compound of the formula I

23. A 2-cyano-3-(halo)alkoxy-benzenesulfonamide compound as defined in claim 22 wherein in formula I Alk is C₁-C₄-haloalkoxy.

24. A 2-cyano-3-(halo)alkoxy-benzenesulfonamide compound as claimed in claim 22 wherein in formula I R¹ is methyl or ethyl.

25. A 2-cyano-3-(halo)alkoxy-benzenesulfonamide compound as claimed in claim 22 wherein in formula I R² is selected from the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₂-C₄-alkinyl.

26. A 2-cyano-3-(halo)alkoxy-benzenesulfonamide compound as claimed in claim 22 wherein R² is methyl, ethyl, 1-methylethyl, cyclopropyl, 2-methoxyethyl, 2-methylthio-ethyl or prop-2-yn-1-yl.

27. A 2-cyano-3-(halo)alkoxy-benzenesulfonamide compound as claimed in claim 22 where in formula I at least one of the radicals R³, R⁴ and R⁵ is different from hydrogen.

28. A 2-cyano-3-(halo)alkoxy-benzenesulfonamide compound as claimed in claim 22 where R³ is halogen.

34. A method for protecting crops from attack or infestation by animal pests which comprises contacting a crop with a pesticidally effective amount of at least one 2-cyano-3-(halo)alkoxy-benzenesulfonamide compound of the general formula I and/or at least one salt thereof as defined in claim 22.

30. An agricultural composition comprising such an amount of at least one 2-cyano-3-(halo)alkoxy-benzenesulfonamide compound of the formula I and/or at least one agriculturally useful salt of I

31. A method of combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, plant, 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 2-cyano-3-(halo)alkoxy-benzenesulfonamide compound of the formula I

32. A method as defined in claim 31 where the animal pest is from the order Homoptera.

33. A method as defined in claim 31 where the animal pest is from the order Thysanoptera.

35. A process for the preparation of 2-cyanophenol compounds VII

36. A method for the protection of 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 a 2-cyano-3-(halo)alkoxy-benzenesulfonamide compound of the general formula I

37. The method according any of claim 36, wherein the compound of formula I is applied in an amount of from 0.1 g to 10 kg per 100 kg of seeds.

38. A method according to claim 36, wherein of the resulting plant'"'"'s roots and shoots are protected.

39. A method according to claim 36, wherein the resulting plant'"'"'s shoots are protected from aphids.

40. Seed comprising the 2-cyano-3-(halo)alkoxy-benzenesulfonamide compound of formula I