Pyrazole derivatives and herbicidal compositions

Details Pyrazole derivatives and herbicidal compositions Pyrazole derivatives and herbicidal compositions

1994-12-27

1996-04-09

Ramsuer, Robert W.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

5483657, A01N 4356, C07D40902

Patent

active

055061940

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP93/00867 filed Jun. 25, 1993.


TECHNICAL FIELD

The present invention relates to pyrazole derivatives, a herbicide containing the pyrazole derivative(s) as an active ingredient, and novel intermediate compounds useful for the production of the pyrazole derivatives.


TECHNICAL BACKGROUND

During a growing period of corn, etc., a triazine-based herbicide such as atrazine and acid anilide-based herbicides such as alachlor and metolachlor have been conventionally used. However, atrazine shows low efficacy to gramineous weeds, and alachlor and metolachlor show low efficacy to broad-leaved weeds. It is therefore difficult at present to control gramineous weeds and broad-leaved weeds together with a single herbicide. Further, the above herbicides are undesirable in view of an environmental problem due to their high dosage requirement.
On the other hand, it is known that specific 4-benzoyl-pyrazole derivatives have herbicidal activity (see JP-A-63-122672, JP-A-63-122673. JP-A-63-170365, JP-A-1-52759, JP-A-2-173 and JP-A-2-288866).
Further, for example, pyrazolate of the following formula is known as a commercial herbicide. ##STR2##
However, pyrazole derivatives having a thiochroman ring such as compounds of the present invention to be specified later are not known yet, and derivatives having an alkoxyimino group are not known, either.
Meanwhile, the commercially available pyrazolate is a herbicide for use in a paddy field., and it hardly has herbicidal activity when used in a plowed field. Further, in foliar treatment, the 4-benzoyl-pyrazole derivatives that have been already disclosed have activity to broad-leaved weeds such as cocklebur, velvetleaf, slender amaranth, etc., in a plowed field, while their activity is practically insufficient. Further, they show very poor activity to grasses such as green foxtail, fingergrass, barnyardgrass, etc. In soil treatment, the above derivatives show very poor activity to grasses such as green foxtail, crabgrass, barnyardgrass, etc, and to broad-leaved weeds such as cocklebur, velvetleaf, slender amaranth, etc.


DISCLOSURE OF THE INVENTION

It is a first object of the present invention to provide a novel pyrazole derivative which shows high selectivity to corn, wheat and barley and which can control grasses and broad-leaved weeds at low dosage by any one of Foliar treatment and soil treatment.
It is a second object of the present invention to provide a herbicide containing the above pyrazole derivative as an active ingredient.
It is a third object of the present invention to provide a novel intermediate compound useful for the production of the above novel pyrazole derivative.
The above first object is achieved by a pyrazole derivative of the formula, ##STR3## (wherein R.sup.1 is a C.sub.1 -C.sub.6 alkyl group, each of R.sup.2, X.sup.1 and X.sup.2 is independently a C.sub.1 -C.sub.4 alkyl group, R.sup.3 is hydrogen or a C.sub.1 -C.sub.4 alkyl group, m is an integer of 0 or 1, and n is an integer of 0, 1 or 2.) or a salt thereof.
The above second object is achieved by a herbicide containing the pyrazole derivative of the above formula (I) and/or a salt thereof as active ingredient.
Further, the above third object is achieved by an aromatic carboxylic acid derivative of the formula, ##STR4## (wherein R.sup.1 is a C.sub.1 -C.sub.6 alkyl group, each of X.sup.1 and X.sup.2 is independently a C.sub.1 -C.sub.4 alkyl group, m is an integer of 0 or 1, and n is an integer of 0, 1 or 2), or a salt thereof.


PREFERRED EMBODIMENTS FOR WORKING THE INVENTION

First, the novel pyrazole derivative of the present invention will be explained.
The novel pyrazole derivative of the present invention includes compounds of the formula (I). ##STR5##
In the formula (i), R.sup.1 is a C.sub.1 -C.sub.6 alkyl group such as methyl., ethyl, propyl, butyl, pentyl or hexyl, and each of R.sup.2, X.sup.1 and X.sup.2 is independently a C.sub.1 -C.sub.4 alkyl group such as methyl, ethyl, propyl such as n-propyl or i-propyl or butyl such as n-butyl. The propyl, butyl, penty

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