Patent EP-2192115-A1 (EP)
Inventor: DUNKEL RALF DR
IPC: A01N43/56
Filed: 2004-10-12
Abstract: 1,3-Dimethylbutyl carboxanilides (I) are new. 1,3-Dimethylbutyl carboxanilides of formula (I) are new. [Image] R 1> : H, 1-8C alkyl, 1-6C alkylsulfinyl, 1-6C alkylsulfonyl, (1-4C)alkoxy(1-4C)alkyl, 3-8C cycloalkyl, 1-6C haloalkyl, 1-4C haloalkylthio, 1-4C haloalkylsulfinyl, 1-4C haloalkylsulfonyl, CHO; 1-3C alkyl substituted with CHO, 2-4C alkanoyl, 1-3C alkoxycarbonyl, 2-4C haloalkanoyl or 1-3C haloalkoxycarbonyl; COR, COCOR 3>, CONR 4>R 5> or CH 2NR 6>R 7>; R : 1-8C alkyl, 1-8C alkoxy, (1-4C)alkoxy(1-4C)alkyl, 3-8C cycloalkyl, 1-6C haloalkyl, 1-6C haloalkoxy, halo(1-4C)alkoxy(1-4C)alkyl or 3-8C halocycloalkyl; R 2> : H, F, Cl, Me or CF 3; R 3> : H or R; R 4>, R 5> : H, 1-8C alkyl, (1-4C)alkoxy(1-4C)alkyl, 3-8C cycloalkyl, 1-6C haloalkyl, halo(1-4C)alkoxy(1-4C)alkyl or 3-8C halocycloalkyl, or NR 4>R 5> is a saturated 5- to 8-membered heterocycle with 0-2 other heteroatoms (O, S or NR 8>), optionally substituted with halo or 1-4C alkyl; R 6>, R 7> : H, 1-8C alkyl, 3-8C cycloalkyl, 1-8C haloalkyl or 3-8C halocycloalkyl, or NR 6>R 7> is a saturated 5- to 8-membered heterocycle with 0-2 other heteroatoms (O, S or NR 8>), optionally substituted with halo or 1-4C alkyl; R 8> : H or 1-6C alkyl; A : a heterocyclic group of formula A1-A14. [Image] [Image] [Image] [Image] R 9> : H, OH, CHO, CN, F. Cl, Br, NO 2, 1-4C (halo)alkyl, 1-4C (halo)alkoxy, 1-4C (halo)alkylthio, CONH 2 or carbamoyl(1-4C)alkyl; R 1> 0> : H, Cl, Br, I, CN, 1-4C alkyl, 1-4C alkoxy or 1-4C (halo)alkylthio; R 1> 1> : H, 1-4C alkyl, 1-4C hydroxyalkyl, 2-6C alkenyl, 3-6C cycloalkyl, (1-4C)(halo)alkylthio(1-4C)alkyl or (1-4C)(halo)alkoxy(1-4C)alkyl; R 1> 2>, R 1> 3>, R 1> 5>, R 1> 6> : H, halo or 1-4C (halo)alkyl; R 1> 4> : halo, CN, 1-4C (halo)alkyl or 1-4C haloalkoxy; R 1> 7> : H or 1-4C (halo)alkyl; R 1> 8> : halo, OH, CN, 1-4C (halo)alkyl, 1-4C (halo)alkoxy or 1-4C (halo)alkylthio; R 1> 9> : H, halo, CN, 1-4C (halo)alkyl, 1-4C (halo)alkoxy, 1-4C alkylsulfinyl or 1-4C alkylsulfonyl; R 2> 0>, R 2> 1> : 1-4C (halo)alkyl; R 2> 2>, R 2> 3> : H, halo, NH 2 or 1-4C (halo)alkyl; R 2> 4> : H or 1-4C (halo)alkyl; R 2> 5>, R 2> 6> : H, halo, NH 2, NO 2 or 1-4C (halo)alkyl; R 2> 8> : H, halo, NH 2, mono- or di(1-4C)alkylamino, CN or 1-4C (halo)alkyl; R 2> 9> : halo, OH, 1-4C (halo)alkyl, 1-4C (halo)alkoxy or 3-6C cycloalkyl; R 3> 0> : H, halo, NH 2, mono- or di(1-4C)alkylamino, CN or 1-4C (halo)alkyl; R 3> 1>, R 27> : halo or 1-4C (halo)alkyl; R 3> 2> : H, halo or 1-4C (halo)alkyl; R 3> 3> : halo, OH, 1-4C (halo)alkyl, 1-4C (halo)alkoxy or 1-4C (halo)alkylthio; R 3> 4> : 1-4C alkyl; provided that R 9> is not CF 2, CHF 2, Me or Et when R 1> 0> : H or Cl, R 1> 1> = Me and R 1> = R 2> = H; R 9> is not Me, CF 2Cl, CF 3, CHF 2, Cl or Br when R 1> 0> = H, F, CF 3 or Me, R 1> 1> = Me, CF 3, CH 2OMe or CH 2OCF 3 and R 1> = COR with R = 1-6C alkyl, 1-6C alkoxy, (1-4C)alkoxy(1-4C)alkyl, 1-6C haloalkyl, 1-6C haloalkoxy or halo(1-4C)alkoxy(1-4C)alkyl; R 1> 4> is not Me when R 1> 2> and R 1> 3> = H or Me and R 1> = R 2> = H; R 1> 8> is not CF 3, Me, Cl or SMe when R 1> 9> is H and R 1> = R 2> = H; R 1> 8> is not Me, CF 2Cl, CF 3, CHF 2, Cl or Br when R 1> 9> = H and R 1> = COR with R = 1-6C alkyl, 1-6C alkoxy, (1-4C)alkoxy(1-4C)alkyl, 1-6C haloalkyl, 1-6C haloalkoxy or halo(1-4C)alkoxy(1-4C)alkyl; R 1> and R 2> are not both H when A = A5; R 2> 4> is not Me when R 2> 2> and R 2> 3> = H or Me and R 1> = R 2> = H; R 2> 9> is not Me, CF 2Cl, CF 3, CHF 2, Cl or Br when R 2> 8> = Me, CF 3, CH 2OMe or CH 2OCF 3 and R 1> = COR with R = 1-6C alkyl, 1-6C alkoxy, (1-4C)alkoxy(1-4C)alkyl, 1-6C haloalkyl, 1-6C haloalkoxy or halo(1-4C)alkoxy(1-4C)alkyl; R 3> 2> is not Cl when R 1> = R 2> = H. An independent claim is also included for a process for preparing (I). ACTIVITY : Plant antifungal; Plant antibacterial; Fungicide. In a protective test against Podosphaera leucotricha on young apple trees, 4-chloro-N-(2-(1,3-dimethylbutyl)phenyl)-5-thiazolecarboxamide had an activity of 100% at an application rate of 100 g/ha. MECHANISM OF ACTION : None given.