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    • 72. 发明专利
    • New oxathiin carboxamide derivatives useful for controlling unwanted microorganisms, especially for protecting plants and materials from attack by fungi and bacteria
    • DE10321270A1
    • 2004-12-02
    • DE10321270
    • 2003-05-13
    • BAYER CROPSCIENCE AG
    • DUNKEL RALFELBE HANS-LUDWIGRIECK HEIKOGREUL JOERG NICOWACHENDORFF-NEUMANN ULRIKEDAHMEN PETERKUCK KARL-HEINZHARTMANN BENOIT
    • A01N37/30A01N43/32C07D327/06
    • Oxathiin carboxamide derivatives (I) are new. Oxathiin carboxamide derivatives of formula (I) are new: [Image] G 1>halo, CF 3, CHF 2 or cyclopropyl; G 2>, G 3>H or Me; R 1>-R 4>H, F, Cl, Me, iPr or SMe; R 5>H; 1-8C alkyl, 1-6C alkylsulfinyl, 1-6C alkylsulfonyl, (1-4C)alkoxy(1-4C)alkyl, 3-8C cycloalkyl, (2-4C)alkanoyl(1-3C)alkyl, (2-4C)alkoxycarbonyl(1-3C)alkyl, all optionally halogenated; formyl(1-3C)alkyl; COR 6>; CONR 7>R 8>; or CH 2NR 9>R 1>0; R 6>H; 1-8C alkyl, 1-8C alkoxy, (1-4C)alkoxy(1-4C)alkyl or 3-8C cycloalkyl, all optionally halogenated; or COR 1> 1>; R 7>,R 8>H; 1-8C alkyl, 1-8C alkoxy, (1-4C)alkoxy(1-4C)alkyl or 3-8C cycloalkyl, all optionally halogenated; or NR 7>R 8> is a 5- to 8-membered saturated heterocycle optionally containing 1-2 other heteroatoms (O, S or NR 1> 2>) and optionally substituted with halo or 1-4C alkyl; R 9>, R 1> 0>H, 1-8C (halo)alkyl, 3-8C (halo)cycloalkyl, or NR 9>R 1>0 is a 5- to 8-membered saturated heterocycle optionally containing 1-2 other heteroatoms (O, S or NR 1> 2>) and optionally substituted with halo or 1-4C alkyl; R 1> 1>H; 1-8C alkyl, 1-8C alkoxy, (1-4C)alkoxy(1-4C)alkyl or 3-8C cycloalkyl, all optionally halogenated; R 1> 2>H or 1-6C alkyl; Z : optionally substituted phenyl; optionally substituted cycloalkyl or bicycloalkyl; or 1-20C alkyl, 2-20C alkenyl or 2-20C alkynyl optionally substituted with halo and/or Q, but not Me; Q : 3-6C cycloalkyl optionally substituted with halo and/or 1-4C alkyl; alternatively, Z+R 4> can form an optionally substituted 5- or 6-membered carbocyclic or heterocyclic ring when R 1>-R 3> are H or F. Independent claims are also included for: (1) 9 processes for preparing (I); (2) halo-substituted oxathiincarboxanilides of formula (IV); (3) oxathiincarboxanilide boronic acid derivatives of formula (VI); (4) hydroxyalkyl-substituted oxathiincarboxanilides of formula (VIII); (5) 2,3-dihydro-3-methyl-6-trifluoromethyl-1,4-oxathiin-5-carboxylic acid, 2,3-dihydro-2-methyl-6-trifluoromethyl-1,4-oxathiin-5-carboxylic acid and 2,3-dihydro-6-cyclopropyl-1,4-oxathiin-5-carboxylic acid; (6) 2-(4-methyl-3-penten-2-yl)aniline, 2-(4-chloro-2-hexyl)aniline and 2-(3-(2,2-dichlorocyclopropyl)-2-propyl)aniline. [Image] X 2>Br or I; A 3>, A 4>H or together form tetramethylethylene; X 5>2-20C hydroxyalkyl optionally substituted with halo and/or Q. ACTIVITY : Plant antifungal; Plant antibacterial; Herbicide; Plant growth regulant. In tests on apple saplings, N-(2-(1,3-dimethylbutyl)phenyl)-2,3-dihydro-6-trifluoromethyl-1,4-oxathiin-5-carboxamide gave 100% protection against attack by Venturia inaequalis at an application rate of 100 g/ha. MECHANISM OF ACTION : None given.