Dithiinopyridazinone derivates
The present invention relates to new dithiinopyridazinone derivatives, to processes for preparing them, to their use for controlling unwanted microorganisms, more particularly phytopathogenic fungi, in crop protection, in the household and hygiene sector and in the protection of materials, and also to crop protection compositions comprising these dithiinopyridazinone derivatives.
1. A dithiinopyridazinone derivative of formula (I)
in which
R 1 and R 2 together are the group —C(═O)—N(R 4 )—N═CH—, whereby the compound of formula (I) comprises a second pyridazinone ring,
R 3 and R 4 are identical or different and are hydrogen, or are C 1 -C 8 -alkyl optionally substituted one or more times by halogen, —OR 5 or —COR 6 , or are C 1 -C 8 -alkoxy, C 1 -C 8 -alkylthio, C 1 -C 8 -haloalkoxy, C 1 -C 8 -haloalkylthio, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino or phenylsulfonylamino, or are C 3 -C 7 -cycloalkyl optionally substituted one or more times by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, or are aryl, aryl-(C 1 -C 4 -alkyl), hetaryl or hetaryl-(C 1 -C 4 -alkyl), each optionally substituted one or more times by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or —COR 6 ,
R 5 is hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkylcarbonyl or is aryl optionally substituted one or more times by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, and
R 6 is hydroxyl, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy,
provided that R 3 and R 4 are not simultaneously hydrogen, methyl, —CH 2 CH 2 CO 2 H, unsubstituted phenyl or unsubstituted benzyl.
2. The dithiinopyridazinone derivative according to claim 1 , having formula (I-b)
in which
R 3b and R 4b are identical or different and are unsubstituted C 2 -C 8 -alkyl, or are C 1 -C 8 -alkyl substituted one or more times by halogen, —OR 5a or —COR 6a , or are C 1 -C 8 -alkoxy, C 1 -C 8 -alkylthio, C 1 -C 8 -haloalkoxy, C 1 -C 8 -haloalkylthio, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino or phenylsulfonylamino, or are C 3 -C 7 -cycloalkyl optionally substituted one or more times by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, or are aryl or aryl-(C 1 -C 4 -alkyl) each substituted one or more times by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or —COR 6b , or are hetaryl or hetaryl-(C 1 -C 4 -alkyl) each optionally substituted one or more times by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or —COR 6b ,
R 5a is hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkylcarbonyl or is aryl optionally substituted one or more times by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl,
R 6a is C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, and
R 6b is hydroxyl, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy.
3. The dithiinopyridazinone derivative according to claim 1 having formula (I-c)
in which
R 3b and R 4b are identical or different and are unsubstituted C 2 -C 8 -alkyl, or are C 1 -C 8 -alkyl substituted one or more times by halogen, —OR 5a or —COR 6a , or are C 1 -C 8 -alkoxy, C 1 -C 8 -alkylthio, C 1 -C 8 -haloalkoxy, C 1 -C 8 -haloalkylthio, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino or phenylsulfonylamino, or are C 3 -C 7 -cycloalkyl optionally substituted one or more times by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, or are aryl or aryl-(C 1 -C 4 -alkyl) each substituted one or more times by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or —COR 6b , or are hetaryl or hetaryl-(C 1 -C 4 -alkyl) each optionally substituted one or more times by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or —COR 6b ,
R 5a is hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkylcarbonyl or is aryl optionally substituted one or more times by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl,
R 6a is C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, and
R 6b is hydroxyl, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy.
4. A composition for controlling unwanted microorganisms, comprising at least one dithiinopyridazinone derivative of formula (I) according to claim 1 and one or more extenders, surface-active substances or a combination thereof.
5. A method for protecting plants or materials from phytopathogenic fungi, comprising administering a dithiinopyridazinone derivative of formula (I) according to claim 1 to the plants, parts of the plants or the materials in need of such protection.
6. A method for controlling unwanted microorganisms, comprising administering a dithiinopyridazinone derivative of formula (I) according to claim 1 to the microorganisms, their habitat or a combination thereof.
7. A process for producing a composition for controlling unwanted microorganisms, comprising mixing a dithiinopyridazinone derivative of formula (I) according to claim 1 with one or more extenders, surface-active substances or a combination thereof.
8. A method for treating a transgenic plant, comprising applying a dithiinopyridazinone derivative of formula (I) according to claim 1 to the transgenic plant in need of such treatment.
9. A composition comprising at least one dithiinopyridazinone derivative of formula (I) according to claim 1 and at least one other active compound selected from the group consisting of insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners and semiochemicals.