US 7,501,530 B2
Trifluoromethyl-thiophene carboxylic acid aniledes and use thereof as fungicides
Markus Gewehr, Kastellaun (Germany); Bernd Müller, Frankenthal (Germany); Thomas Grote, Wachenheim (Germany); Wassilios Grammenos, Ludwigshafen (Germany); Andreas Gypser, Mannheim (Germany); Jordi Tormo i Blasco, Laudenbach (Germany); Anja Schwögler, Mannheim (Germany); Joachim Rheinheimer, Ludwigshafen (Germany); Carsten Blettner, Mannheim (Germany); Frank Schieweck, Heβheim (Germany); Michael Rack, Heidelberg (Germany); Ulrich Schöfl, Brühl (Germany); Siegfried Strathmann, Limburgerhof (Germany); Reinhard Stierl, Freinsheim (Germany); and Jan Rether, Kaiserslautern (Germany)
Assigned to BASF Aktiengesellschaft, Ludwigshafen (Germany)
Appl. No. 10/548,840
PCT Filed Mar. 20, 2004, PCT No. PCT/EP2004/002933
§ 371(c)(1), (2), (4) Date Sep. 12, 2005,
PCT Pub. No. WO2004/085419, PCT Pub. Date Oct. 07, 2004.
Claims priority of application No. 103 13 126 (DE), filed on Mar. 24, 2003; and application No. 103 54 549 (DE), filed on Nov. 21, 2003.
Prior Publication US 2006/0172891 A1, Aug. 03, 2006
Int. Cl. C07D 333/22 (2006.01); C07C 333/32 (2006.01); A01N 25/00 (2006.01); C07C 335/00 (2006.01); A01N 25/32 (2006.01)
U.S. Cl. 549—72  [549/64; 424/405] 13 Claims
 
1. A trifluoromethylthiophenecarboxanilide of the formulae I, II and III

OG Complex Work Unit Drawing
in which the substituents are as defined below:
R1, R4 independently of one another are C1-C4-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy (it being possible for these groups to be substituted by halogen), H, halogen, nitro, CN;
R2 is C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy (it being possible for these groups to be substituted by halogen), H, OH;
R3 is C1-C12-alkyl, C3-C12-cycloalkyl, C2-C12-alkenyl, C5-C12-cycloalkenyl, C2-C12-alkynyl, C3-C12-cycloalkyl-C1-C4-alkyl (it being possible for these groups to be substituted by R7);
phenyl, phenyl-C1-C6-alkyl, phenyl-C2-C6-alkenyl, phenyl-C2-C6-alkynyl, phenyloxy-C1-C6-alkyl, phenyloxy-C2-C6-alkenyl, phenyloxy-C2-C6-alkynyl, where the alkyl, alkenyl and alkynyl moiety may be substituted by R7 and the phenyl ring may be substituted by R5;
—C(R8)═NOR6;
X is O, S or a direct bond;
R5 is H, C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl (it being possible for these groups to be substituted by halogen), halogen, nitro, CN, phenyl (which may be substituted by R1), phenoxy (which may be substituted by R1), C1-C6-alkylphenyl, where the alkyl moiety may be substituted by halogen and the phenyl ring may be substituted by R1;
R6 is C1-C4-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, C2-C4-alkynyl (it being possible for these groups to be substituted by halogen), phenyl, which may be substituted by R1;
R7 is C1-C4-alkyl, C1-C8-alkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy, C1-C4-alkoxy-C1-C8-alkoxy (it being possible for these groups to be substituted by halogen), halogen;
R8 is H, R7 or C1-C12-alkyl, C3-C12-cycloalkyl, C2-C12-alkenyl, C5-C12-cycloalkenyl, C3-C12-cycloalkyl-C1-C4-alkyl (it being possible for these groups to be substituted by halogen);
phenyl, which may be substituted by R5;
n is 0-4;
m is 0, 1.