4-thiocarbamoyl-1-(3-pyrazolyl)-pyrazoles and their use as herbi

Details 4-thiocarbamoyl-1-(3-pyrazolyl)-pyrazoles and their use as herbi 4-thiocarbamoyl-1-(3-pyrazolyl)-pyrazoles and their use as herbi

1998-02-26

2000-02-15

Ramsuer, Robert W.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

504282, A01N 4356, C07D23138

Patent

active

06025498&

DESCRIPTION:

BRIEF SUMMARY
The invention relates to novel 4-thiocarbamoyl-1-(3-pyrazolyl)-pyrazoles, to a process for their preparation and to their use as herbicides.
Substituted pyrazolylpyrazoles are already known as potential herbicides (cf. EP 542388, WO 9408999). However, these compounds have not achieved any particular importance.
This invention, accordingly, provides the novel 4-thiocarbamoyl-l-(3-pyrazolyl)-pyrazoles of the general formula (I) ##STR2## in which
R.sup.1 represents optionally substituted alkyl,
R.sup.2 represents a respectively optionally substituted radical from the group consisting of alkyl, alkoxy and alkylthio, or together with R.sup.1 represents the grouping --(CH.sub.2).sub.m --X--,
R.sup.3 represents hydrogen or halogen,
R.sup.4 represents hydrogen or represents optionally substituted alkyl,
R.sup.5 represents hydrogen, cyano, nitro, thiocarbamoyl or halogen, represents optionally substituted alkyl, represents optionally substituted aryl, represents the grouping --O--R.sup.6, the grouping --S(O).sub.n --R.sup.7, the grouping --NR.sup.8 R.sup.9 or the grouping --NR.sup.10 --CY--R.sup.11,
R.sup.6 represents hydrogen or represents respectively optionally substituted alkyl, alkenyl or alkinyl,
R.sup.7 represents a respectively optionally substituted radical from the group consisting of alkyl, alkenyl and alkinyl,
R.sup.8 represents hydrogen or represents a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl and arylalkyl,
R.sup.9 represents hydrogen or represents a respectively optionally substituted radical from the group consisting of alkyl, alkoxy, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl and aralkyl or represents the grouping --S(O)--R.sup.7, or together with R.sup.8 represents alkanediyl,
R.sup.10 represents hydrogen or represents a respectively optionally substituted radical from the group consisting of alkyl, alkenyl and alkinyl,
R.sup.11 represents hydrogen, represents optionally substituted alkyl or represents optionally substituted aryl,
m represents the numbers 2 or 3,
n represents the numbers O, 1 or 2,
x represents CH.sub.2, O, S, S(O).sub.n, NH or NCH.sub.3, and
Y represents O or S.
The novel 4-thiocarbamoyl-1-(3-pyrazolyl)-pyrazoles of the general formula (I) are obtained when 4-cyano-1-(3-pyrazolyl)-pyrazoles of the general formula (II) ##STR3## in which
R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each as defined above,
are reacted with hydrogen sulphide, thioacetic acid or thioacetamide, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.
The novel 4-thiocarbamoyl-1-(3-pyrazolyl)-pyrazoles of the general formula (I) have strong herbicidal activity.
In the definitions, the saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkinyl, are each, even in combination with hetero atoms, such as in alkoxy or alkylthio, straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
The invention preferably provides compounds of the formula (I) in which
R.sup.1 represents optionally cyano-, halogen- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl having 1 to 6 carbon atoms,
R.sup.2 represents a respectively optionally cyano-, halogen- or C.sub.1 -C.sub.4 -alkoxy-substituted radical from the group consisting of alkyl, alkoxy and alkylthio having in each case 1 to 6 carbon atoms, or together with R.sup.1 represents the grouping --(CH.sub.2).sub.m --X--,
R.sup.3 represents hydrogen or halogen,
R.sup.4 represents hydrogen or represents optionally cyano-, halogen- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl having 1 to 6 carbon atoms,
R.sup.5 represents hydrogen, cyano, nitro, thiocarbamoyl or halogen, represents optionally cyano-, halogen- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents optionally cyano-, nitro-, halogen-, C.sub.1 -C.sub.4 -alkyl-, C.sub.1 -C.sub.4 -halogenoalkyl-,

REFERENCES:
patent: 5756424 (1998-05-01), Dorfmeister

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