Heterocyclic cyclohexanedione derivative, production thereof, an

Details Heterocyclic cyclohexanedione derivative, production thereof, an Heterocyclic cyclohexanedione derivative, production thereof, an

1994-07-20

1996-04-02

Rotman, Alan L.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

546193, 546194, 546242, 546243, 549 28, 549285, 504244, C07D21140, C07D21114, A01N 4340

Patent

active

055040560

DESCRIPTION:

BRIEF SUMMARY
CROSS-REFERENCE

This application is a 35 U.S.C. .sctn.371 National Stage application of PCT/JP92/00877 filed on Jul. 8, 1992.
1. Field of the Invention
The present invention relates to a heterocyclic cyclohexanedione derivative, a process for production thereof, and a herbicide comprising the same.
2. Background of the Invention
In agricultural and horticultural crop farming, many herbicides have been used for weed control which requires extraordinary labours. However, there have been several cases which caused phytotoxicity problems and environmental pollution such as residue problems therefore, it is required to develop a new chemical entity which can provide firm effectiveness with a lower dosage and can be used safely is in a high demand.
It is an object of the present invention to provide a herbicide which can be synthesized advantageously in a industrial scale and having a property such as high effectiveness at lower dosage, highly safe, and high selectivity on crops.


DISCLOSURE OF THE INVENTION

The present invention is directed to a heterocyclic cyclohexanedione derivative represented by the general formula I!; ##STR2## wherein R.sup.1 is optionally substituted lower alkyl, optionally substituted cycloalkyl, optionally substituted phenyl or optionally substituted heterocyclic ring; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 may be the same or different from one another and each represents hydrogen or lower alkyl; R.sup.6 is hydrogen; R.sup.7 is OR.sup.8 wherein R.sup.8 is hydrogen, lower alkyl, aralkyl, lower acyl, alkylsulfonyl, or arylsulfonyl; or R.sup.6 and R.sup.7 are combined together to represent a single bond; X is oxygen, sulfur or N--R.sup.9 wherein R.sup.9 is hydrogen, lower alkyl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted phenyl or optionally substituted heterocyclic ring, or a salt thereof, a process for producing the same, and a herbicide comprising the same.
The substituents such as lower alkyl, cycloalkyl, phenyl and heterocyclic ring for R.sup.1 may be the same or different from one another and each independently represents halogen, hydroxy, nitro, cyano, alkyl except when R.sup.1 is lower alkyl, alkenyl, haloalkyl except when R.sup.1 is lower alkyl, alkoxyalkyl except when R.sup.1 is lower alkyl, alkoxyalkoxyalkyl except when R.sup.1 is lower alkyl, alkoxycarbonylalkyl except when R.sup.1 is lower alkyl, haloalkenyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, haloalkenyloxy, alkoxyalkoxy, alkylthioalkoxy, alkylthio, alkenylthio, alkynylthio, haloalkylthio, haloalkenylthio, monoalkylamino, dialkylamino, alkoxyakylthio, alkylthioalkylthio, alkoxycarbonyl, alkylcarbonylalkoxy, alkylcarbonyl, alkoxyamino, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, alkoxyalkylsulfonyl, alkylthioalkylsulfonyl, alkylsulfonylalkylsulfonyl, haloalkylsulfonyl, alkoxycarbonylalkylthio, alkylsulfinylalkoxycarbonylalkylsulfinyl, alkoxycarbonylalkylsulfonyl, alkylamide, aralkyloxy, optionally substituted phenyl, optionally substituted aralkyl, optionally substituted heterocyclic ring, or alkyl substituted by optionally substituted heterocyclic ring.
Heterocyclic ring represents pyridyl, pyrimidyl, thienyl, furyl, pirazolyl, pyrrolyl, imidazolyl, pyridazinyl, pirazinyl, indolyl, or the like.
The compounds of the present invention can be produced according to the following process. ##STR3## wherein R.sup.1 through R.sup.5 and X are as defined above, Q is a leaving group which represents halogen, alkylsulfonate, arylsulfonate, or the like.
In the process as illustrated above, compound I'! is obtained by reacting a compound II! in a solvent and in the presence of 2 mol or excessive concentration of a base for 30 minutes to several 10 hours at the temperature of from -20.degree. C. to a boiling point of a solvent used, preferably from 0.degree. C. to 50.degree. C.
For the base described above, alkali metal hydroxides such as KOH and NaOH, alkaline earth metal hydroxides, tri(C.sub.1 -C.sub.6 alkyl)amine, pyridine, DBU, t-BuOK, triton B, sodium carbonate, sodium ph

REFERENCES:
patent: 4761172 (1988-08-01), Dieter et al.
patent: 4812160 (1989-03-01), Dieter et al.
patent: 4921524 (1990-05-01), Dieter et al.

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