Substituted 5-aminopyrazoles

Details Substituted 5-aminopyrazoles Substituted 5-aminopyrazoles

1993-06-07

1996-01-23

Killos, Paul J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

5483561, C07D23100

Patent

active

054866189

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to novel 5-aminopyrazoles of the general formula I ##STR2## where R.sup.1 is C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -hydroxyalkyl may carry or a phenyl group which may carry from one to three of the following radicals: halogen, nitro, C.sub.1 -C.sub.4 -alkyl, partially or completely halogenated C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, partially or completely halogenated C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or --NR.sup.6 R.sup.7, where R.sup.6 and R.sup.7 are each hydrogen or C.sub.1 -C.sub.4 -alkyl, and the phenyl group may additionally carry a further number of halogen atoms so that the total number of radicals is 4 or 5; or partially or completely halogenated; C.sub.1 -C.sub.4 -alkoxy, amino, C.sub.1 -C.sub.4 -alkylamino or di-C.sub.1 -C.sub.4 -alkylamino; PX(OR.sup.5).sub.2, SO.sub.2 --R.sup.9, CX--R.sup.10, CX--NH--CY--R.sup.9 or CX--NH--SO.sub.2 --R.sup.11, where group which may carry from one to three of the following radicals: halogen, nitro, C.sub.1 -C.sub.4 -alkyl, partially or completely halogenated C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, partially or completely halogenated C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or --NR.sup.6 R.sup.7, and which may additionally carry a further number of halogen atoms so that the total number of radicals is 5; amino which may be unsubstituted or may carry a C.sub.1 -C.sub.4 -alkyl, cycloalkyl or phenyl radical, where the phenyl radical in turn may carry from one to three of the following radicals: halogen, C.sub.1 -C.sub.4 -alkyl, partially or completely halogenated C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, partially or completely halogenated C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio and the phenyl group may additionally contain a further number of halogen atoms so that the total number of radicals is 4 or 5; -alkylamino, pyrrolidinyl, piperidinyl or morpholinyl; --CO--W--CO--, where R.sup.12 is hydrogen, amino, C.sub.1 -C.sub.4 -alkylamino or C.sub.3 -C.sub.8 -cycloalkylamino; -alkylamino, C.sub.3 -C.sub.8 -cycloalkylamino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, phenyl or pyridyl, where the two last-mentioned substituents may furthermore carry from one to three of the following radicals: halogen, nitro, C.sub.1 -C.sub.4 -alkyl, partially or completely halogenated C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, partially or completely halogenated C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio; 1,2-C-bonded aromatic or heteroaromatic bridge having a nitrogen, oxygen or sulfur atom as hetero atom, where these bridge members may furthermore carry, on each substitutable carbon atom, a radical selected from up to 2 of the following: halogen, C.sub.1 -C.sub.4 -alkyl, partially or completely halogenated C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, partially or completely halogenated C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio and partially or completely halogenated C.sub.1 -C.sub.4 -alkylthio, and where the bridge members may additionally carry a number of halogen atoms equivalent to the number of further substitutable carbon atoms, or bridge, where these substituents may furthermore carry from one to four of the following radicals: halogen or C.sub.1 -C.sub.4 -alkyl; or hydroxythiocarbonyl and the acidic salts of the compounds I which contain a basic nitrogen atom, 1-methyl-4-cyano-5-(chloromethylcarbonylamino)-pyrazole, 1-methyl-4-cyano-5-(phenylcarbonylamino)-pyrazole, 1-methyl-4-cyano-5-(p-chlorophenylcarbonylamino)-pyrazole, and the compounds I in which R.sup.1 was methyl, phenyl, 4-chlorophenyl or 4-nitrophenyl, R.sup.2 was hydrogen, methyl or trifluoromethyl, R.sup.3 was cyano and R.sup.4 and R.sup.5 were simultaneously hydrogen.
The present invention furthermore relates to a process for the preparation of the compounds I and to herbicides containing one or more herbicidal active ingredients from the group consisting of the formula X ##STR3## where R.sup.a is phenyl, pyridyl, benzoxazyl, benzothiazyl or benzopyrazinyl,

REFERENCES:
patent: 4734122 (1988-03-01), Gehring et al.
patent: 4808623 (1989-02-01), Ooms et al.
Chem Abst 115:49681 Jan. 30, 1991
Chem Abst 111: 57677 19889.
Synthesis of 5-Aminopyrazole-4-Carbonitriles, Dooley et al., Aust. J. Chem 1989, 42, 747-50.
J. Org. Chem. 21 (1956), 1240.
J. Heterocycl. Chem. 12 (1975), 1199.
Bull. Chem. Soc. Jpn. 60 (1987).

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