Benzoylpyrazole compounds, intermediate preparing therefor and h

Details Benzoylpyrazole compounds, intermediate preparing therefor and h Benzoylpyrazole compounds, intermediate preparing therefor and h

1998-12-08

2000-11-14

Lambkin, Deborah C.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

548240, A01N 4380, C07D26102

Patent

active

061470317

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP98/04898 Oct. 29, 1998.


TECHNICAL FIELD

The present invention relates to a novel pyrazole compound substituted with a benzoyl group at the 4 position of the pyrazole ring and a herbicide.


BACKGROUND ART

For culturing agrohorticultural crops, many herbicides have been used to control weeds, which required great labor. Herbicides applied, however, have caused chemical injuries on crops, or remained in or polluted the environment. It is therefore wanted to develop chemicals firmly effective at a smaller dosage thereof and applicable safely. As herbicides having a pyrazole skeleton substituted by a benzoyl group at the 4 position of the pyrazole ring, Tokkaihei(Japanese Patent Laid-Open Hei) No. 2-173 has disclosed compounds represented by General formula [A] ##STR2##
WO93/18031 Gazette has disclosed compounds represented by formula [B] ##STR3##
WO96/26206 Gazette has disclosed compounds represented by formula [C]. ##STR4##
It is an object of this invention to provide a herbicide that can be advantageously synthesized on an industrial scale, is firmly effective at a lower dosage, and selectively work on weeds without damaging crops.


DISCLOSURE OF THE INVENTION

That is to say, the present invention is directed to a compound represented by General formula [I] ##STR5## [wherein R.sup.1 is a C.sub.1 -C.sub.6 alkyl group; R.sup.2 is a C.sub.1 -C.sub.6 alkylthio group or a C.sub.1 -C.sub.6 alkylsulfonyl group; R.sup.3 and R.sup.4 are each independently hydrogen or a C.sub.1 -C.sub.6 alkyl group; R.sup.5 is hydrogen or a group selected from the group represented by the following formula ##STR6## (where R.sup.6 is halogen, a C.sub.1 -C.sub.6 alkyl group or a C.sub.1 -C.sub.6 alkoxy group; and n is 0, 1, 2, 3, 4 or 5); R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are each independently hydrogen or a C.sub.1 -C.sub.6 alkyl group; and (R.sup.7 or R.sup.8) and (R.sup.9 or R.sup.10) may form a single bond], or a salt thereof, and a herbicide containing one or more of the said compounds as active ingredients.
In General formula [I] illustrated above, R.sup.1 is a C.sub.1 -C.sub.6 alkyl group, such as methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl and t-butyl. R.sup.2 is a C.sub.1 -C.sub.6 alkylthio group, such as methylthio, ethylthio, propylthio and isopropylthio or a C.sub.1 -C.sub.6 alkylsulfonyl group, such as methylsulfonyl, ethylsulfonyl, propylsulfonyl and isopropylsulfonyl.
R.sup.3 and R.sup.4 are each independently hydrogen or a C.sub.1 -C.sub.6 alkyl group, such as methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl and t-butyl.
R.sup.5 is hydrogen or the group represented by the above formula. Examples include a phenylsulfonyl group which may have substituent R.sup.6, a benzyl group which may have substituent R.sup.6, and a phenacyl group which may have substituent R.sup.6.
Preferred examples include phenylsulfonyl, tosyl, 2,4,6-trimethylphenylsulfonyl, benzyl, 4-chlorobenzyl, 4-methylbenzyl, 4-methoxybenzyl, phenacyl, 4-methylphenacyl, and 3,5-dichlorophenacyl.
R.sup.6 is hydrogen, halogen such as fluorine, chlorine and bromine; a C.sub.1 -C.sub.6 alkyl group such as methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl and t-butyl; or a C.sub.1 -C.sub.6 alkoxy group such as methoxy, ethoxy, propoxy, isopropoxy, butoxy and t-butoxy.
R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are each independently hydrogen or a C.sub.1 -C.sub.6 alkyl group, such as methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl and t-butyl. (R.sup.7 or R.sup.8) and (R.sup.9 or R.sup.11) may form a single bond.
Further, the present invention provides a benzoic acid or a benzoic acid ester which are raw materials of the said compounds represented by the above general formula [I]; a general formula (1) ##STR7## (wherein R.sup.1, R.sup.2, R.sup.7 to R.sup.10 are as defined above, and R is hydrogen or a C.sub.1 -C.sub.6 alkyl group.).
R.sup.1, R.sup.2, R.sup.7 to R.sup.10 are as defined above in a general formula (1).
R is hydrogen or a straight chain or branching C.sub.1 -C.sub.6 alkyl group such as methyl, ethy

REFERENCES:
patent: 5834402 (1998-11-01), Von Deyn et al.
patent: 5846907 (1998-12-01), Von Deyn et al.

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