5-amino-1-phenyl-pyrazole herbicides and plant growth regulators
AssigneeBayer Aktiengesellschaft
InventorsReinhold Gehring, Otto Schallner, Jorg Stetter, Hans-Joachim Santel, Robert R. Schmidt, Klaus Lurssen
Life of this patent
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Abstract
Herbicidal and plant growth regulating 5-amino-1-phenyl-pyrazoles of the formula ##STR1## in which R.sup.1 to R.sup.4 each represents hydrogen or various organic radicals, X represents oxygen or sulphur, n represents the number 0, 1 or 2, and m represents the number 1, 2 or 3, but wherein, in the case where R.sup.1 and R.sup.3 represent hydrogen and R.sup.2 represents nitro, R.sup.4 does not simultaneously represent a propionyl radical.
Claims15
A 5-amino-1-phenyl-pyrazole of the formula ##STR96## in which R.sup.1 represents hydrogen, or represents straight-chain or branched alkyl with 1 to 8 carbon atoms,
- R.sup.2 represents hydrogen, nitro, nitroso, fluorine, chlorine, bromine or iodine, or represents a radical ##STR97## wherein R.sup.5 represents hydrogen, hydroxyl or straight-chain or branched alkyl with 1 to 8 carbon atoms, or represents in each case straight-chain or branched alkenyl, alkinyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio, alkylamino, dialkylamino or halogenoalkyl with in each case up to 4 carbon atoms in the individual alkyl parts and, in the case of the halogenoalkyl, with up to 9 identical or different halogen atoms, or furthermore represent cycloalkyl which has 3 to 7 carbon atoms and is optionally monosubstituted or polysubstituted by identical or different substituents from the group comprising halogen, C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.4 -halogenoalkyl, or represents phenyl, phenoxy, phenylthio or phenylamino, in each case optionally substituted on the phenyl by halogen, alkyl, alkoxy or halogenoalkyl with in each case 1 to 4 carbon atoms and, if appropriate, up to 9 halogen atoms,
- R.sup.3 represents hydrogen, or represents a radical ##STR98## or represents a radical --S(O).sub.n --R.sup.7 and R.sup.4 represents hydrogen, or represents a radical ##STR99## or represents a radical --S(O).sub.n --R.sup.7, or represents straight-chain or branched alkyl with 1 to 6 carbon atoms, or, in the case where R.sup.3 represents a radical --SO.sub.2 --R.sup.7 or a radical --CO--C.sub.m F.sub.2m+1, also represents one equivalent of an alkali metal cation, alkaline earth metal cation or transition metal cation, bonded in salt form, or represents an ammonium ion, which is unsubstituted or mono- or polysubstituted by identical or different substituents from the group consisting of C.sub.1 -C.sub.6 -alkyl, phenyl and benzyl,
- wherein
- R.sup.6 represents hydrogen, or represents straight-chain or branched alkyl with 1 to 12 carbon atoms, or represents in each case straight-chain or branched alkenyl or alkinyl with in each case 2 to 4 carbon atoms, or represents in each case straight-chain or branched alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio, alkylsulphonyalkyl, alkylsulphinylalkyl, alkylamino, dialkylamino or halogenoalkyl with in each case 1 to 4 carbon atoms in the individual alkyl parts and, in the case of the halogenoalkyl, with up to 9 identical or different halogen atoms, or furthermore represents cycloalkyl which has 3 to 7 carbon atoms and is optionally monosubstituted or polysubstituted by identical or different substituents from the group consisting of halogen, C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.4 -halogenoalkyl, or represents phenyl, phenoxy, phenylthio or phenylamino, in each case optionally substituted on the phenyl by halogen, alkyl, alkoxy or halogenoalkyl with in each case 1 to 4 carbon atoms and, if appropriate, up to 9 halogen atoms, and
- X represents oxygen or sulphur,
- n represents the number 0, 1 or 2,
- m represents the number 1, 2 or 3 and
- R.sup.7 represents in each case straight-chain or branched alkyl or halogenoalkyl with in each case 1 to 4 carbon atoms and, if appropriate, 1 to 9 identical or different halogen atoms, or represents phenyl which is optionally substituted by halogen, alkyl, alkoxy or halogenoalkyl with in each case 1 to 4 carbon atoms and, if appropriate, up to 9 identical or different halogen atoms, but wherein, in the case where R.sup.1 and R.sup.3 represents hydrogen and R.sup.2 represents nitro, R.sup.4 does not simultaneously represents a propionyl radical.
A compound according to claim 7, wherein such compound is 5-amino-4-ethoxycarbonyl-1-(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl)- pyrazole of the formula ##STR106##
A 5-amino-1-phenyl-pyrazole selected from the group consisting of
- 5-amino-4-ethoxycarbonyl-1-(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl)-p yrazole,
- 5-acetamido-1-(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl)-pyrazole,
- 5-amino-4-nitro-1-(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl)-pyrazole,
- 5-methoxyacetamido-4-nitro-1-(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl) -pyrazole,
- 5-.alpha.-chloropropionamido-4-nitro-1-(2,3,5,6-tetrafluoro-4-trifluorometh yl-phenyl)-pyrazole, and
- 4-nitro-5-methyl-carbonylamino-1-(2,3,5,6-tetrafluoro-4-trifluoromethyl-phe nyl)-pyrazole.
Dependencies are inferred from the claim text.