Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-02-03
1995-07-04
Ivy, C. Warren
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
546156, 546157, 544 3, 544107, 544 63, 544224, 544333, C07D21538, C07D215227, C07D21518
Patent
active
054301530
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
Field of the Invention
The present invention relates to novel 2-quinolinone derivatives of the following general fomula(I) useful in agriculture, especially as fungicides but also as insecticides and miticides. ##STR2## 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, branched C.sub.3 -C.sub.4 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, alkoxy carbonyl, phcnyl, substituted phenyl, phenoxy, substituted phenozxy, benzenesulfonyl, benzyl, substituted benzyl or morpholine; -C.sub.6 cycloalkyl, phenyl, substituted phenyl, benzyl or phenylthio methyl; and branched C.sub.3 -C.sub.6 alkyl, C.sub.1 -C.sub.3 haloalkyl, benzyl or substituted benzyl, and R.sub.8 is phenyl, substituted phenyl, benzyl or substituted benzyl; -C.sub.6 cycloalkyl, phenyl or substituted phenyl; 6-membered cyclic ring or fused ring, optionally including a hetero atom selected from O or N, or optionally substituted with C.sub.1 -C.sub.3 alkyl or carbocyclic ring including N atom, or one of A and B is H and the other is R.sub.10 or Z--Ar; and then, C.sub.3 -C.sub.8 alkyl or C.sub.3 -C.sub.6 cycloalkyl optionally including a hetero atom selected from O, S or N or optionally substituted with C.sub.1 -C.sub.3 alkyl or alkoxycarbonyl, C.sub.1 -C.sub.3 haloalkyl, alkoxyalkyl, alkoxycarbonylalkyl, phenyl, substituted phenyl, pyridyl, substituted pyridyl, pyrimidyl, or substituted pyrimidyl; ring, or optionally substituted with C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 hydroxyalkyl or or phenyl; and pyridyl, substituted pyridyl, or a phenyl group of the following formula (II) ##STR3## wherein, R.sub.11, R.sub.12, R.sub.13, R.sub.14 and R.sub.15 are independently H, halogen, C.sub.1 -C.sub.6 alkyl, branched C.sub.3 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, phenyl, phenoxy, phenylthio, CN, NO.sub.2, NH.sub.2, or SO.sub.2 NH.sub.2.
Description of the Prior Art
There is an acute need for new fungicities, insecticides, and miticides, because target pathogens are rapidly developing resistance to currently used pesticides. The development of resistance to some of the fungicides in current use, such as the triazoles, the benzimidazoles, the acylalanines, and the organophosphates and the insecticides, such as the carbamates, the organophosphates, and the pyrethroids, is well known. Therefore a need exists for new fungitides, insecticides, and miticides.
SUMMARY OF THE INVENTION
The present invention relates to novel 2-quinolinone derivatives having the above general formula(I), which have fungicidal and insecticidal activity.
DETAILED DESCRIPTION OF THE INVENTION
The compounds of the general formula(I) according to the present invention can be prepared by reactions as described herein below.
The compounds(Ia) of general formula(I) wherein X is SR.sub.6, and then R.sub.6 is R.sub.7, can be made by thermally cyclizing compounds of following formula(III), and the compounds(Ib) of general formula(I) wherein X is SOR.sub.6, and then R.sub.6 is R.sub.7, may be prepared by oxidizing the corresponding compounds(Ia) using a conventional oxidation procedure. ##STR4## wherein, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.7 are as previously defined.
The above reaction may be camed out without solvent or under the presence of solvent, for example, hydrocarbon solvents such as paraffin oil, benzenes such as xylene and dichlorobenzene, amides such as dimethyl formamide and dimethyl acetamide, anilines such as N,N-dimethylaniline and N,N-diethyl aniline, ethers such as diphenyl ether, or a mixture of them.
The cyclizing reaction is camed out at 140.degree..about.250.degree. C., preferably 160.degree..about.200.degree. C. If the temperature is lower than 140.degree. C., the reaction rate is very slow, and ff higher than 250.degree. C., it is attended with the severe evolution of mercaptan(R.sub.7 SH) as a
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Choi Eun B.
Chung Young R.
Kim Heung T.
Kim Sung K.
Lee Ge H.
Ivy C. Warren
Korea Research Institute of Chemical Technology
M. Mach D. Margaret
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