4-amino-2-quinolinone derivatives

Details 4-amino-2-quinolinone derivatives 4-amino-2-quinolinone derivatives

1995-12-19

1998-01-13

Ivy, C. Warren

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

546156, A61K 3147, C07D21530

Patent

active

057079315

DESCRIPTION:

BRIEF SUMMARY
This is the U.S. national stage application of PCT/KR94/00079 filed Jun. 21, 1994, published as WO/95/00488 on Jan. 5, 1995.


BACKGROUND OF THE INVENTION

Field of the Invention
The present invention relates to novel 4-amino-2-quinolinone derivatives of the following formula (I) useful as fungicides, insecticides and herbicides. ##STR3## wherein, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently hydrogen, halogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkylthio, NO.sub.2, CN, C.sub.1 -C.sub.4 alkoxy carbonyl, phenyl, phenoxy, benzoyl, benzenesulfonyl, benzyl or morpholine; or phenylthiomethyl; alkenyl and C.sub.3 -C.sub.6 alkynyl group; ##STR4## wherein, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15, R.sub.16 is hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, alkoxyalkyl, halophenyl, phenyl or (R.sub.20).sub.3 Si and R.sub.8, R.sub.9, R.sub.10 are not hydrogen at the same time;
Description of the Related Art
Prior to this invention, one report on the synthesis of 3-acetyl-4-dimethylamino-2-quinolinone from phenylisocynate and Chim. Acta., 1969, 52, 2641.) was disclosed but no attempt for the evaluation of biological activity of the related compounds was reported.
According to the known methods, it is difficult to introduce various substituents to aromatic ring, 4-amino group, and 3-acyl group of 2-quinolinone skeleton.
Especially, synthesis of 4-monosubstituted amino-2-quinolinones which are core of the present invention is impossible to be produced by known methods.
In the present invention, variety of new 4-amino-2-quinolinone derivatives having various substituents were synthesized conveniently from various amines and 4-sulfinyl-2-quinolinones of which synthesis was previously disclosed by present inventors (Korea Patent No.70672).
Moreover new 4-amino-2-quinolinone derivatives of the present invention showed powerful fungicidal activity as well as insecticidal and herbicidal activity.
Therefore, the present invention contains development of novel 4-amino-2-quinolinone derivatives that have superior fungicide, insecticide and herbicide activities and their preparation for use.


SUMMARY OF THE INVENTION

The objective of the present invention is to provide novel 4-amino-2-quinolinone derivatives of formula (I) which have fungicidal, insecticidal and herbicidal activity and their preparation processes.
Another objective is to provide agricultural preparation containing a compound of formula (I) as active ingredient.


DETAILED DESCRIPTION OF THE INVENTION

The present invention relates to 4-amino-2-quinolinone compounds of the formula (I) and agricultural preparations containing compounds of the formula (I) as active ingredient. ##STR5## wherein, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are respectively defined as described previously.
In this invention, 4-amino-2-quinolinone compounds of the formula (I) were prepared by reacting 4-sulfinyl-2-quinolinone of formula (II) with the amines (HNR.sub.6 R.sub.7) of the formula (III) in presence of inert solvent. ##STR6## wherein, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are defined as previously and R.sub.21 is C.sub.1 -C.sub.3 alkyl.
When the amine compound of formula (III) is in salt form, such as primary or secondary ammonium hydrochlorides (HNR.sub.6 R.sub.7 --HCl), sulfates, carbonates, oxalates or tosylates, 1.about.2 equivalents of an acid remover, for example, trialkylamines (such as triethylamine) or inorganic base (such as sodium hydroxide, potassium carbonate), may be used.
The inert solvents used in the present invention may be, for example, ethers such as diethylether, diisopropyl ether, tetrahydrofuran, dioxane, diphenylether, etc.; hydrocarbons such as benzene, toluene, xylene, ligroine, etc.; hydrocarbon halides such as dichloroethane, chloroform, carbon tetrachloride, etc.; esters such as ethyl acetate, ethyl propionate, etc.; chlorobenzenes such as

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