Cyclohexanedione derivatives

Details Cyclohexanedione derivatives Cyclohexanedione derivatives

1995-01-13

1996-01-02

Hollrah, Glennon H.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504292, 549 23, 549 28, 549401, 549403, A01N 4318, A01N 4316, C07D33506

Patent

active

054808588

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to a cyclohexanedione derivative. More specifically it relates to a novel cyclohexanedione derivative, a process for the production thereof and a herbicide containing the cyclohexanedione derivative as an active ingredient.


TECHNICAL BACKGROUND

During a growing period of corn, etc., a triazine-containing herbicide such as atrazine and acetoanilide-containing 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 using a single herbicide. Further, the use of these chemicals in combination fails to give any sufficient effect. Moreover, 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 benzoylcylohexanedione derivatives have herbicidal activity (see JP-B-1-30818, JP-A-61-155347, JP-A-1-143851, JP-A-3-120202, EP 135,191, EP 186,118A, EP 186,119A, U.S. Pat. No. 4,954,165, GB 2,215,333A, EP 336,898A, U.S. Pat. Nos. 4,937,386, 4,780,127, 5,092,919 and PCT International Publication 90/05712). Typical examples of the above benzoylcyclo-hexanedione derivatives are as follows. ##STR2##
Further, JP-A-64-6256 discloses cyclohexanedione derivatives having a fused dicyclic group containing heteroatoms. ##STR3##
However, cyclohexanedione derivatives having a thiochroman ring such as compounds of the present invention are not known yet.
Further, the cyclohexanedione derivatives that have been already disclosed are insufficient in practical use, particularly poor in herbicidal activity to gramineous weeds such as barnyardgrass and green foxtail.
It is therefore a first object of the present invention to provide a novel cyclohexanedione derivative which exhibits high selectivity for corn, wheat and barley and can control both gramineous weeds and broad-leaved weeds at low dosage.
It is a second object of the present invention to provide a process for the production of the above novel cyclohexanedione derivative.
Further, it is a third object of the present invention to provide a herbicide containing the above novel cyclohexanedione derivative as an active ingredient.


DISCLOSURE OF THE INVENTION

The novel cyclohexanedione derivative of the present invention, which achieves the first object of the present invention, is a compound of the formula (I). ##STR4##
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. The propyl, butyl, pentyl and hexyl may be linear or branched. R.sup.1 is preferably a C.sub.1 -C.sub.4 alkyl group, more preferably methyl, ethyl or isopropyl.
R.sup.2 is a C.sub.1 -C.sub.4 alkyl group such as methyl, ethyl, propyl or butyl. The propyl and butyl may be linear or branched. R.sup.2 is preferably methyl.
Each of R.sup.3, R.sup.4 and R.sup.5 is independently hydrogen or a C.sub.1 -C.sub.4 alkyl. The C.sub.1 -C.sub.4 alkyl group includes those described regarding the above R.sup.2. Each of R.sup.3, R.sup.4 and R.sup.5 is preferably hydrogen or methyl. The site where R.sup.3 is substituted is preferably the 8-position on a thiochroman ring. Further, both R.sup.4 and R.sup.5 are preferably substituted on the same carbon atom of a cyclohexane-1,3-dione ring, and the site where each of R.sup.4 and R.sup.5 is preferably the 4-position.
The suffix "n" indicates the number of oxygen atom(s) bonded to a sulfur atom, and n is an integer of 0 to 2. That is, when n=0, sulfide is represented. When n=1, sulfoxide is represented. When n=2, sulfone is represented. The sulfone form (n=2) is preferred.
Specific examples of the cyclohexanedione derivative of the formula (I) are preferably as shown in Table (A).


TABLE (A) ______________________________________ ##STR5## Compound No. R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 n _____________________________

REFERENCES:
patent: 4741755 (1988-05-01), Knudsen et al.
patent: 4895868 (1990-01-01), Chandraratna
patent: 5006150 (1991-04-01), Lee et al.
patent: 5074903 (1991-12-01), Jahn et al.
patent: 5114461 (1992-05-01), Geach et al.
patent: 5132434 (1992-07-01), Watanabe et al.
patent: 5424320 (1995-06-01), Fortin et al.

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