Substituted pyrazole derivatives and their use as herbicides

Details Substituted pyrazole derivatives and their use as herbicides Substituted pyrazole derivatives and their use as herbicides

1995-06-01

1998-05-26

Ramsuer, Robert W.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

546121, 5483601, A01N 4356, C07D47104

Patent

active

057564248

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP93/0281 filed Oct. 11, 1993.


FIELD OF THE INVENTION

This invention relates to new substituted pyrazole derivatives, their preparation, as well as intermediates, and their use as herbicides.


PRIOR ART

It is known that 1-phenylpyrazoles possess herbicidal activity (EP 154115).
However the herbicidal activity of these compounds in not high enough or selectivity problems can occur in important crops.
The object of the present invention is to make new compounds that have improved biological properties over the known compounds.
It has now been found that substituted pyrazole derivatives of general formula I ##STR2## in which
R.sup.1 is C.sub.1 -C.sub.4 -alkyl;
R.sup.2 is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkoxy, each of which is optionally substituted by one or more halogen atoms, or
R.sup.1 and R.sup.2 together form the group --(CH.sub.2).sub.m ;
R.sup.3 is hydrogen or halogen,
R.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl,
R.sup.5 is hydrogen, nitro, cyano or the groups --COOR.sup.7, --C(.dbd.X)NR.sup.8 R.sup.9 or --C(.dbd.X)R.sup.10,
R.sup.6 is hydrogen, halogen, cyano, C.sub.1 -C.sub.4 -alkyl, (optionally substituted by one or more halogen or hydroxy groups), C.sub.1 -C.sub.4 -alkoxy, phenyl, (optionally substituted by one or more halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halo-C.sub.1 -C.sub.4 -alkyl groups), pyrrolyl, or is a C.sub.2 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -alkenyl, C.sub.3 -C.sub.8 -alkynyl or C.sub.3 -C.sub.8 -alkoxy group, each of which is interrupted by one or more oxygen atoms, or is the group; NR.sup.11 R.sup.12 ; ##STR3##
R.sup.7, R.sup.8 and R.sup.9, which may be the same or different, are hydrogen or C.sub.1 -C.sub.4 -alkyl or
R.sup.8 and R.sup.9 together with the nitrogen to which they are attached form a 5 or 6 membered saturated carbocyclic ring;
R.sup.10 is hydrogen or C.sub.1 -C.sub.4 -alkyl, optionally substituted by one or more halogen atoms,
R.sup.11 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or phenyl (each of which is optionally substituted by one or more halogen atoms), C.sub.3 -C.sub.8 -cycloalkyl, cyanomethyl or the group R.sup.21 CO--;
R.sup.12 is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or phenyl (each of which is optionally substituted by one or more halogen atoms), C.sub.3 -C.sub.8 -cycloalkyl, cyanomethyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 -alkyl, di-C.sub.1 -C.sub.4 -alkylamino-C.sub.1 -C.sub.4 -alkyl, tetrahydrofurfurylmethyl, C.sub.3 -C.sub.6 -alkynyl-oxy-C.sub.1 -C.sub.4 -alkyl, benzyl, (optionally substituted by one or more halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halo-C.sub.1 -C.sub.4 -alkyl groups), or is the group --C(.dbd.X)R.sup.21, --(CH.sub.2).sub.a --(O).sub.d --R.sup.28, --(CH.sub.2).sub.a --O--(CH.sub.2).sub.b- R.sup.28 or --(CH.sub.2).sub.a --X--R.sup.34, and when R.sup.5 is --C(.dbd.O)R.sup.10, and/or when R.sup.1 is C.sub.1 -C.sub.4 -alkyl, R.sup.2 is difluoromethoxy, R.sup.3 is bromo and R.sup.5 is nitro or cyano, R.sup.12 can also be hydrogen; or
R.sup.11 and R.sup.12 together with the nitrogen to which they are attached form a 3, 5 or 6 membered saturated carbocyclic or aromatic ring, in which a carbon atom is optionally substituted by an oxygen atom;
R.sup.13 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl; or R.sup.13 and R.sup.14 together form the group --(CH.sub.2).sub.p ;
R.sup.14 and R.sup.15, which may be the same or different, are C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or phenyl (each of which is optionally substituted by one or more halogen atoms), hydrogen, C.sub.3 -C.sub.6 -cycloalkyl or the groups --XR.sup.18 or --NR.sup.19 R.sup.20 ;
R.sup.16 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkylcarbonyl, cyano-C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.4 -alk

REFERENCES:
patent: 3993469 (1976-11-01), Regel et al.
patent: 5104439 (1992-04-01), Schallner et al.
patent: 5405829 (1995-04-01), Hartfiel et al.
A. Fruchier et al. Constantes d'acidite de quelques biheterocycles, Journal of Heterocyclic Chemistry vol. 26, 1989, pp. 893-898.

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