Oxathiin carboxamides
View Patent ↗This invention relates to novel oxathiincarboxamides of the formula (I) in which G 1 , G 2 , G 3 , n, R 1 , R 2 , R 3 , R 4 , R 5 and Z are as defined in the disclosure, to a plurality of processes for preparing these compounds and their use for controlling unwanted microorganisms, and to novel intermediates and their preparation.
1. An oxathiincarboxamide of formula (I)
in which
G 1 represents halogen, trifluoromethyl, difluoromethyl, or cyclopropyl,
G 2 and G 3 independently of one another represent hydrogen or methyl,
n represents 0, 1 or 2,
R 1 , R 2 , R 3 , and R 4 independently of one another represent hydrogen, fluorine, chlorine, methyl, isopropyl, or methylthio,
R 5 represents hydrogen, C 1 -C 8 -alkyl, —COR 6 , or —CONR 7 R 8 ,
R 6 represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -cycloalkyl; represents C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms; or represents —COR 11 ,
R 7 and R 8 independently of one another represent hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -cycloalkyl; represent C 1 -C 8 -haloalkyl, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms; or R 7 and R 8 together with the nitrogen atom to which they are attached form a saturated heterocycle having 5 to 8 ring atoms, where the heterocycle is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl,
R 11 represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -cycloalkyl; represents C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms, and
Z represents Z 3 , where
Z 3 represents unsubstituted C 5 -C 20 -alkyl or represents C 1 -C 20 -alkyl that is mono- or polysubstituted by identical or different substituents selected from the group consisting of chlorine and C 3 -C 6 -cycloalkyl.
2. The oxathiincarboxamide of formula (I) as claimed in claim 1 in which
n represents 0 or 2.
3. The oxathiincarboxamide of formula (I) as claimed in claim 1 in which R 5 represents hydrogen.
4. The oxathiincarboxamide of formula (I) as claimed in claim 1 in which
R 1 represents hydrogen, fluorine, chlorine, or methyl,
R 2 represents hydrogen, fluorine, chlorine, isopropyl, or methylthio,
R 3 represents hydrogen, fluorine, chlorine, or methyl, and
R 4 represents hydrogen, fluorine, chlorine, or methyl.
5. A composition for controlling unwanted microorganisms comprising one or more oxathiincarboxamides of formula (I) as claimed in claim 1 and one or more extenders and/or surfactants.
6. A hydroxyalkyloxathiincarboxamide of formula (VIII)
in which
G 1 represents trifluoromethyl, difluoromethyl, or cyclopropyl,
G 2 and G 3 independently of one another represent hydrogen or methyl,
n represents 0, 1 or 2,
R 1 , R 2 , R 3 , and R 4 independently of one another represent hydrogen, fluorine, chlorine, methyl, isopropyl, or methylthio,
R 5 represents hydrogen, C 1 -C 8 -alkyl, —COR 6 , or —CONR 7 R 8 ,
R 6 represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -cycloalkyl; represents C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms; or represents —COR 11 ,
R 7 and R 8 independently of one another represent hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -cycloalkyl; represent C 1 -C 8 -haloalkyl, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms; or R 7 and R 8 together with the nitrogen atom to which they are attached form a saturated heterocycle having 5 to 8 ring atoms, where the heterocycle is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl,
R 11 represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -cycloalkyl; represents C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms, and
X 5 represents C 2 -C 20 -hydroxyalkyl that is optionally additionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C 3 -C 6 -cycloalkyl.