Abstract:
The present invention relates to novel 2-quinolinone derivanves of the following general formula(I) useful in agriculture, especially as fungicides but also as insecticides and miticides. ##STR1## wherein, R 1 , R 2 , R 3  and R 4  are independently hydrogen, halogen, C 1  -C 10  alkyl, branched C c  -C 4  alkyl, C 1  -C 3  haloalkyl, C 1  -C 3  alkoxy, C 1  -C 3  haloalkoxy, C 1  -C 3  alkylthio, C 1  -C 3  haloallcylthio, NO 2 , CN, alkoxy carbonyl, phenyl, substituted phenyl, phenoxy, substituted phenoxy, benzenesulfonyl, benzyi, substituted benzyl or morpholine; 
     R 5  is C 1  -C 6  alkyl, branched C 3  -C 6  alkyl, C 3  -C 6  cycloalkyl, phenyl, substituted phenyl, benzyl or phenylthio methyl: and 
     X is S(O)nR 6 , OR 9  or NAB: 
     wherein. 
     n is 0 or 1; 
     R 6 , R 9 , A and B are defined within the description.

Description:
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 1 , R 2 , R 3  and R 4  are independently hydrogen, halogen, C 1  -C 10  alkyl, branched C 3  -C 4  alkyl, C 1  -C 3  haloalkyl, C 1  -C 8  alkoxy, C 1  -C 3  haloalkoxy, C 1  -C 3  alkylthio, C 1  -C 3  haloalkylthio, NO 2 , CN, alkoxy carbonyl, phcnyl, substituted phenyl, phenoxy, substituted phenozxy, benzenesulfonyl, benzyl, substituted benzyl or morpholine; 
     R 5  is C 1  -C 6  alkyl, branched C 3  -C 6  alkyl. C 3  -C 6  cycloalkyl, phenyl, substituted phenyl, benzyl or phenylthio methyl; and 
     X is S(O)nR 6 , OR 9  or NAB: 
     wherein, 
     n is 0 or 1: 
     R 6  is R 7  or R 8 , and then R 7  is C 1  -C 6  alkyl, branched C 3  -C 6  alkyl, C 1  -C 3  haloalkyl, benzyl or substituted benzyl, and R 8  is phenyl, substituted phenyl, benzyl or substituted benzyl; 
     R 9  is C 2  -C 5  alkyl, branched C 3  -C 4  alkyl, C 5  -C 6  cycloalkyl, phenyl or substituted phenyl; 
     A and B are combined together to fonn a saturated or unsaturated 5 or 6-membered cyclic ring or fused ring, optionally including a hetero atom selected from O or N, or optionally substituted with C 1  -C 3  alkyl or carbocyclic ring including N atom, or one of A and B is H and the other is R 10  or Z--Ar; and then, 
     R 10  is saturated or unsaturated C 1  -C 10  alkyl, branched C 3  -C 8  alkyl or C 3  -C 6  cycloalkyl optionally including a hetero atom selected from O, S or N or optionally substituted with C 1  -C 3  alkyl or alkoxycarbonyl, C 1  -C 3  haloalkyl, alkoxyalkyl, alkoxycarbonylalkyl, phenyl, substituted phenyl, pyridyl, substituted pyridyl, pyrimidyl, or substituted pyrimidyl; 
     Z is C 1  -C 4  alkyl chain, optionally containing cyclopropylene ring, or optionally substituted with C 1  -C 3  alkyl, C 1  -C 3  alkoxy, C 1  -C 3  hydroxyalkyl or or phenyl; and 
     Ar is C 3  -C 6  cycloalkyl, optionally including a nitrogen atom, or pyridyl, substituted pyridyl, or a phenyl group of the following formula (II) ##STR3## wherein, R 11 , R 12 , R 13 , R 14  and R 15  are independently H, halogen, C 1  -C 6  alkyl, branched C 3  -C 4  alkyl, C 1  -C 4  haloalkyl, C 1  -C 4  alkoxy, phenyl, phenoxy, phenylthio, CN, NO 2 , NH 2 , or SO 2  NH 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 6 , and then R 6  is R 7 , can be made by thermally cyclizing compounds of following formula(III), and the compounds(Ib) of general formula(I) wherein X is SOR 6 , and then R 6  is R 7 , may be prepared by oxidizing the corresponding compounds(Ia) using a conventional oxidation procedure. ##STR4## wherein, R 1 , R 2 , R 3 , R 4 , R 5  and R 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°˜250° C., preferably 160°˜200° C. If the temperature is lower than 140° C., the reaction rate is very slow, and ff higher than 250° C., it is attended with the severe evolution of mercaptan(R 7  SH) as a by-product. 
     Alteratively, the compounds(Ia&#39;) of general formula(I) wherein X is SR 6 , and then R 6  is R 8 , can be manufactured by reacting the compounds of above formula(Ib) with thiol of following formula(IV), and the compounds(Ib&#39;) wherein X is SOR 6 , and then R 6  is R 8 , can be prepared by oxidizing the corresponding compounds(Ia&#39;) using a conventional oxidation procedure. ##STR5## wherein, R 1 , R 2 , R 3 , R 4 , R 5  and R 8  are as previously defined. 
     The compounds of above formula(Ia&#39;) can be prepared by the substitution reaction heating 4-alkylsulfoxyquinolinone of the above formula(Ib) and thiophenol derivative of the above formula(IV) without solvent or under the presence of solvent, and then the solvent as the above, e.g. hydrocarbons, benzenes, amides, anilines, ethers, or their mixture, may be used. 
     The substitution reaction is carried out at 100°˜250° C., preferably 160°˜200° C. If the temperature is lower than 100° C., the reacting rate is very slow, and if higher than 250° C., the yields are very low. 
     The compounds(when n in X of formula(I) is 1 ) of the formula(Ib) and (Ib&#39;) can be prepared by oxidation of the compounds(when n in X of formula(I) is 0 ) of the formula(Ia) and (Ia&#39;) using a conventional oxidants, for example, organic or inorganic peroxy compounds such as hydrogen peroxide, potassium peroxymonosulfate, tertiary butyl hydroperoxide, m-chloro peroxybenzoic acid, peroxyacetic acid, and magnesium monoperoxyphthalate. 
     And then, solvent may be used as followings; water; hydrocarbon halide such as dichloromethane, chloroform, carbon tetrachloride, and chlorobenzene; aliphatic acid such as acetic acid and propionic acid; or alcohols such as methyl alcohol, ethyl alcohol, etc. 
     The reaction may be carried out at 0°˜130° C., preferably 20°˜60° C., and then if the temperature is lower than 0° C., the reaction rate is very slow, and if higher than 130° C., the used solvent may be boiled over. 
     The amount of used oxidant may be usefully 1.2 fold or more with the used compound of the formula(Ia) or (Ia&#39;), but it is not limited specially. 
     The quinolinone derivatives of the formula(Ia) and (Ib&#39;) and sulfoxy-2-quinolinone derivatives may be optionally recrystallized or purified by chromatography. 
     The compounds(Ic) of general formula(I) wherein X is OR 9  and then R 9  is methyl can be prepared by the known process described in J. Org. Chem. Vol. 31, P1276-1278(1966) or J. Org. Chem. Vol. 34, P2183-2187(1969) by J. W. Huffman and J. H. Cecil. Especially, 3-isobutyryl-4-methoxy-(2H)quinolinone, 3-isobutyryl- 4,8-dimethoxy-2(1H)-quinolinone, 3-isovaleryl-4-methoxy-2(1H)-quinolinone or 3-isovaleryl-4,8-dimethoxy-2(1H)-quinolinone were prepared in 14˜18% yields by reacting the corresponding 3-acyl-4-hydroxy-2(1H)-quinolinone with diazomethane, and separation of the resulted mixture of 2(1H)-quinolinone, 1-methyl-2(1H)-quinolinone and other products as using liquid chromatography. 
     In this invention, the compounds(Ic) of general formula(I) wherein X is OR 9  were made by condensing the compounds of formula(Ib) with an alcohol of the formula(V). ##STR6## wherein, R 1 , R 2 , R 3 , R 4 , R 5  and R 9  are as previously defined. 
     Also, the above compound(Ic) may be prepared by substitution of alcohols(R 9  OH) under heating without solvent or under the presence of a solvent, or directly using alcohol as a solvent, and then the base may be used or not. 
     The used solvent may be, excepting alcohol used as a reactant, dimethyl formamide, acetonitrile, dioxane, benzene, toluene, xylene, tetrahydrofuran, hexane, heptane, or a mixture of them. The base may be, for example, pyridine, triethylamine, N,N-dialkylaniline, alkalimetal hydroxide, alkalimetal carbonate, metal hydride, etc. 
     The substitution reaction is carded out at boiling point of solvent or between room temperature and 200° C., preferably at 50°˜120° C. 
     The compounds(Id) of general formula(l) wherein X is NAB and then NAB is NMe 2  can be prepared by the known process described in Helv. Chim. Acta., Vol. 52, P 264˜2657(1969) by H. J. Gais, K. Hafiner and M. Neuenschwander. Especially, 3-acetyl-4,8- (dimethylamino)- 2(1H)-quinolinone may be obtained by reaction of phenylisocyanate and 1-dimethytamino-3-oxo-1-butylene according to [4+2]cycloaddition. 
     In this invention, the compounds(Id) of general formula(I) wherein X is NAB were prepared by condensing the compounds of formula(Ib) with the amines of the formula(VI) ##STR7## wherein, R 1 , R 2 , R 3 , R 4 , R 5 , A and B are as previously defined. 
     The above compound(Id) a be prepared by reacting 4-alkylsulfoxy-2-quinolinone of the above formula(Ib) with an amine compound of the following formula(VI) under the presence of inert solvent. 
     When the amine compound of formula(VI) is acid salt, an acid remover for example, trialkylamines (such as triethylamine), potassium carbonate, inorganic base (such as sodium hydroxide), may be used, as adding 1˜2 equivalents, and thereafter acid adding salt of amine compound is added. 
     An inert solvent 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 monochlorobenzene, dichlorobenzene, etc.; aprotic polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, etc., but the above reaction may be carried out without solvent. 
     According to the present invention, pyridine or trialkylamine may be used as two purposes of a base and a solvent. The reaction can be carried out at 0°˜260° C., preferably between room temperature and boling point of the solvent, and then the reacting time is preferable of 0.5˜8 hr but it is affected by the reaction temperature. 
     As a result of the reaction, when the amine compound of formula(VI) being not acid adding salt is used, the crude product is obtained by evaporating the solvent under the reduced pressure. 
     But, when the amine compound of formula(VI) being acid adding salt is used, the crude product may be obtained by following process; the solvent is evaporated under the reduced pressure; water is added to dissolve the salts; the resulting mixture is extracted with water-insoluble organic solvent such as methylenechloride, chloroform, ethyl acetate, etc.; and the organic layer is evaporated under the reduced pressure to afford the crude product. 
     The obtained 2-quinolinone derivatives of formula(Id) may be purified by column chromatography or recrystallized by the following solvent; alcohol solvent such as methanol, ethanol, etc.; ester of organic acid such as ethyl acetate, methyl acetate, etc.; hydrocarbon solvent such as pentane, hexane, etc.; ether such as ethylether, tetrahydrofuran, etc. 
     On the other hand, the starting material used in the present invention, ketene dithio acetal α-anilide of the formula(IH), can be prepared from β-ketoanilide by the following reaction process ##STR8## wherein, R 1 , R 2 , R 3 , R 4 , R 5  and R 7  is respectively as the above defined, Y is chlorine, bromine, iodine, or alkyl or arylsulfonate. 
     The compounds according to the present invention have highly curative and protective fung icidal activity for plant germs of widely spectrum as followings; for example, rice blast (Piricularia oryzae), rice sheath blight (Rhizoctonia solani), cucumber gray mold (Botrytis cinerea), cucumber powdery mildew (Sphaerotheca fuliginea), cucumber downy mildew (Pseudoperonospora cubensis), grape downy mildew (Plasmopora viticola), tomato late blight (Phytophthora infestans), rice brown spot (Cochliobolus miyabeanus), peanut brown leaf spot (Cercospora arachidicola), barley powdery mildew (Erysiphe graminis), wheat leaf rust (Puccinia recondita), wheat stem rust (Puccinis graminis), and wheat eye spot (Pseudocercosporella herpotrichoides). Also, the compounds according to the present invention have highly insecticidal activity for noxious insects, for example, house fly, mosquito, cockroach and agricultral insects, for example, Hemiptera such as small brown plant hopper (Laodephax striatellus Fallen), brown plant hopper (Nilaparvata lugens Stail), white-backed rice plant hopper (Sogatella furcifera Horvath), green rice leaf hopper (Nephotettix cincticeps Uhler), greenhouse white fly (Trialeurodes vaporariorum Westwood), and green peach aphid (Myzus persicae Sulzer); Lepidoptera such as apple leafminer (Phyllonorycter ringoniella Matsumura), diamond-back moth (Plutella xylostella Curtis), rice armyworm (Pseuclaletia separata Walker), cabbage armyworm (Mamestra brassicae Linnaeus), tobacco cutworm (Spodoptera litura Fablicius), and common cabbage worm(Pieris rapae Linnaeus); Coleoptera such as rice leaf beetle (Oulema oryzae Kuiwayarna), and rice-plant weevil rice curculio (Echinocnemus squameus Billbery). 
     Useful formulations of the compounds of formula(I) can be prepared by mixing the compounds of active ingredient of about 0.01˜90 weight % with proper solid or liquid carrier and supporters such as surfactant, diluent, spreader, synergist, adhesive, dispersant, etc. 
     The used solid carrier may be usually chosen from among the attapulgite clays, the montmorillonite clays, the diatomaceous earths, or the purified silicates, and liquid carrier may be water, alcohol, methanol, ethanol, acetone, dimethylformamide, ether, benzene, xylene, toluene, naphtha, etc. 
     Suffactant may be nonionic suffactant(e.g., polyoxy ethylene alkylphenylether and poly oxyethylene fatty acid ester), artionic suffactant(alkyl benzenesulfonic acid, lignine sulfonate and dinaphthalene methane sulfonate), etc. Polyvinylalcohol, CMC, gum arabic, etc. may be used as adhesive. 
     The fungicidal and insecticidal compositions using the compounds of the present invention may be manufactured as formulation such as powder, wettable powder, granules, emulsifiable concentrates, suspensions, solution, fumigant, gas phase, etc., and thekr fonnulations were used in earth, agriculural products, seedling, seeds, etc. 
     For example, emulsifiable concentrates or solution may be prepaxed by uniformly dissolving the compound of formula(I) with hydrocarbon, acetone or alcohol and surfactant. 
     Wettable powders, which may be compacted to form water dispersible granules, comprise an intimate mixture of the active compound, inert carder and surfactants. 
     The combinations including the compounds according to the present invention may be used by mixing with agricultural chemicals such as insecticides, fungicides, herbicides, plant growth regulants, miticides, etc. 
     Especially, since the known fungicides have resistance, the compounds of formula(I) of more than 1 weight % may be used with the known fungicides including following compounds; 
     1) N-substituted azoles, for example, prochloraz, triademefon, and flusilazol; 
     2) pyrimidines, such as fenarimol and nuarimol; 
     3) morpholines, such as fenpropimorph and tridemorph; 
     4) piperazines, such as triforine; 
     5) pyridines, such as pyrifenox; 
     6) dithiocarbamates, such as maneb and mancozeb; 
     7) phthalimides, such as captafol; 
     8) isophthalonitriles, such as chlorothalonil; 
     9) dicarboximides, such as iprodione; 
     10) benzimidazoles, such as benomyl and carbendazim; 
     11) 2-aminopyrimidines, such as ethirimol; 
     12) carboxamides, such as carboxin; and 
     13) dinitrophenols, such as dinocap. 
     The fungicide combinations of the invention contain at least 1%, generally 20˜80% by weight of a compound of formula (1). 
     The compounds of said formula(D according to the present invention specify as the following Tables 1˜4; 
     
                                           TABLE 1__________________________________________________________________________4-alkyl or arylthio-2-quinolinone(I-a, I-a&#39;) and 4-alkyl orarylsulfoxy-2-quinolinone(I-b, I-b&#39;) ##STR9##Comp. No. R.sub.1    R.sub.2           R.sub.3              R.sub.4                   R.sub.5                         R.sub.5     n m.p. (°C.)__________________________________________________________________________1     H  H      H  H    CH.sub.3                         CH.sub.3    0 226-2312     &#34;  &#34;      OCH.sub.3              &#34;    &#34;     &#34;           &#34; 194-1993     &#34;  &#34;      H  Cl   &#34;     &#34;           &#34; 135-1374     Cl &#34;      &#34;  Cl   &#34;     &#34;           &#34; 171-1755     H  OCH.sub.3           &#34;  H    &#34;     &#34;           &#34; 232-2336     &#34;  H      F  &#34;    &#34;     &#34;           &#34; 225-2277     &#34;  F      H  &#34;    &#34;     &#34;           &#34; 233-2358     &#34;  H      &#34;  F    &#34;     &#34;           &#34; 139-1419     &#34;  &#34;      &#34;  Cl   n-C.sub.3 H.sub.7                         &#34;           &#34; 110-11210    &#34;  &#34;      &#34;  &#34;    C.sub.2 H.sub.5                         &#34;           &#34; 130-13111    &#34;  &#34;      &#34;  CH.sub.3                   CH.sub.3                         &#34;           &#34; 93-9412    &#34;  &#34;      &#34;  Cl   C.sub.6 H.sub.5                         &#34;           &#34; 199-20213    &#34;  Cl     &#34;  CF.sub.3                   CH.sub.3                         &#34;           &#34; 118-12114    &#34;  H      &#34;  H    C.sub.6 H.sub.5                         &#34;           &#34; 265-26815    &#34;  &#34;      &#34;  F    CH.sub.3                          ##STR10##  &#34; 109-11116    H  H      H  CO.sub.2 CH.sub.3                   CH.sub.3                         CH.sub.3    0 233-23417    &#34;  Cl     &#34;  H    &#34;     &#34;           &#34; 197-19818    &#34;  H      &#34;  NO.sub.2                   &#34;     &#34;           &#34; 184-18519    NO.sub.2    &#34;      &#34;  Cl   &#34;     &#34;           &#34; 201-20320    H  NO.sub.2           &#34;  H    &#34;     &#34;           &#34; 222-22621    &#34;  Cl     NO.sub.2              H    &#34;     &#34;           &#34; 281-28322    &#34;  H      H  CN   &#34;     &#34;           &#34; 171-17323    &#34;  Cl     &#34;  CF.sub.3                   CH.sub.3                          ##STR11##  &#34; 110-11324    &#34;  t-Bu   &#34;  H    &#34;     CH.sub.3    &#34; 154-15625    &#34;  H      &#34;  SO.sub.2 C.sub.6 H.sub.5                   &#34;     &#34;           &#34; 211-21326    NO.sub.2    &#34;      &#34;  F    &#34;     &#34;           &#34; &gt;26027    Cl Cl     Cl Cl   &#34;     &#34;           &#34; 188-19128    H  CF.sub.3           H  H    &#34;     &#34;           &#34; 151-15329    &#34;  H      &#34;  CF.sub.3                   &#34;     &#34;           &#34; 98-9930    &#34;  Br     &#34;  &#34;    &#34;     &#34;           &#34; 139-14131    &#34;  H      &#34;  SCF.sub.3                   CClFH &#34;           &#34; 127-12932    &#34;  OC.sub.5 H.sub.11 -n           &#34;  H    &#34;     &#34;           &#34; 134-13733    &#34;  F      &#34;  CF.sub.3                   &#34;     &#34;           &#34; 138-14034    &#34;  H      F  &#34;    &#34;     &#34;           &#34; 164-16635    &#34;  Br     CF.sub.3              H    &#34;     &#34;           &#34; 138-14036    &#34;  Cl     &#34;  &#34;    &#34;     &#34;           &#34; 149-15137    &#34;  n-C.sub.6 H.sub.13           H  &#34;    &#34;     &#34;           &#34; 94-9838    &#34;  F      F  F    &#34;     &#34;           &#34; 132-13439    &#34;  Cl     H  CF.sub.3                   &#34;                          ##STR12##  &#34; 143-14440    &#34;  F      Cl H    &#34;     CH.sub.3    &#34; 141-14341    CF.sub.3    H      H  Cl   &#34;     &#34;           &#34; 206-20842    H  Cl     H  CH.sub.3                   CH.sub.3                         CH.sub.3    0 164-16643    &#34;  H      &#34;  C.sub.2 H.sub.5                   &#34;     &#34;           &#34; 87-8844    &#34;  &#34;      &#34;  &#34;    &#34;                          ##STR13##  &#34; 116-11745    &#34;  CF.sub.3           Cl H    &#34;     CH.sub.3    &#34; 149-15146    &#34;  H      &#34;  Cl   &#34;     &#34;           &#34; 143-14447    &#34;  t-Bu   H  H    &#34;                          ##STR14##  &#34; 118-12048    &#34;  H      &#34;  CN   &#34;                          ##STR15##  &#34; 115-11649    &#34;  CF.sub.3           &#34;  NO.sub.2                   &#34;     CH.sub.3    &#34; 156-15750    H  Cl     Cl H    CH.sub.3                         CH.sub.3    &#34; 150-15251    Cl &#34;      H  &#34;    &#34;     &#34;           &#34; 223-22552    H  H      CF.sub.3              &#34;    &#34;     &#34;           &#34; 135-13853    &#34;  Cl     H  Cl   &#34;                          ##STR16##  &#34; 215-21754    &#34;  &#34;      &#34;  CF.sub.3                   &#34;                          ##STR17##  &#34; 179-18155    Cl H      &#34;  Cl   &#34;                          ##STR18##  &#34; 184-18556    H  Cl     &#34;  &#34;    &#34;                          ##STR19##  &#34; 101-10257    &#34;  &#34;      &#34;  CH.sub.3                   &#34;                          ##STR20##  &#34; 162-16358    &#34;  &#34;      &#34;  &#34;    &#34;                          ##STR21##  &#34; 158-16059    Cl H      &#34;  &#34;    &#34;     CH.sub.3    &#34; 164-16560    CH.sub.3    &#34;      CH.sub.3              H    &#34;     &#34;           &#34; 151-15361    Cl &#34;      H  Cl   &#34;     n-C.sub.4 H.sub.9                                     &#34; 105-10662    H  &#34;      &#34;  i-C.sub.3 H.sub.7                   &#34;     CH.sub.3    &#34; 101-10263    Cl &#34;      Cl H    &#34;     &#34;           &#34; 165-16664    H  &#34;      H  CF.sub.3                   &#34;     n-C.sub.4 H.sub.9                                     &#34; 91-9365    &#34;  &#34;      &#34;  C.sub.6 H.sub.5                   &#34;     CH.sub.3    &#34; 131-13266    &#34;  &#34;      &#34;  &#34;    &#34;     n-C.sub.4 H.sub.9                                     &#34; 84-8767    &#34;  &#34;      &#34;  &#34;    &#34;                          ##STR22##  &#34; 123-12668    H  H      H  C.sub.6 H.sub.5                   CH.sub.3                          ##STR23##  0 82-8369    CH.sub.3    &#34;      &#34;  Cl   &#34;     CH.sub.3    &#34; 159-16170    H  CH.sub.3           &#34;  CH.sub.3                   &#34;                          ##STR24##  &#34; 138-13971    Cl H      &#34;  Cl   &#34;                          ##STR25##  &#34; 155-15672    H  H      H  i-C.sub.3 H.sub.7                   CH.sub.3                          ##STR26##  &#34; 117-11973    &#34;  &#34;      &#34;  &#34;    &#34;     n-C.sub.4 H.sub.9                                     &#34; 44-4574    &#34;  &#34;      &#34;  CH.sub.2 C.sub.6 H.sub.5                   &#34;     CH.sub.3    &#34; 135-13775    &#34;  Cl     &#34;  CF.sub.3                   &#34;     C.sub.2 H.sub.5                                     &#34; 87-8976    &#34;  H      &#34;  n-C.sub.3 H.sub.7                   &#34;     CH.sub.3    &#34; 73-7477    &#34;  &#34;      Cl CH.sub.3                   &#34;     CH.sub.3    &#34; 132-13578    &#34;  Cl     H  CF.sub.3                   &#34;     n-C.sub.6 H.sub.13                                     &#34; 66-6879    &#34;  CH.sub.3           Cl H    &#34;     CH.sub.3    &#34; 143-14580    Cl &#34;      H  &#34;    &#34;     &#34;           &#34; 156-15881    H  H      &#34;  CH.sub.2 C.sub.6 H.sub.5                   &#34;     n-C.sub.4 H.sub.9                                     &#34; 80-8182    &#34;  &#34;      &#34;  &#34;    &#34;     i-C.sub.5 H.sub.11                                     &#34; 66-6783    &#34;  Cl     &#34;  F    &#34;     CH.sub.3    &#34; 153-15684    &#34;  NO.sub.2           &#34;  Cl   &#34;     &#34;           &#34; 197-19885    CH.sub.3    H      &#34;  &#34;    &#34;     &#34;           &#34; 161-16286    H  F      &#34;  &#34;    &#34;     &#34;           &#34; 146-14787    CF.sub.3    H      &#34;  OCH.sub.3                   &#34;     &#34;           &#34; 259-26188    H  OCH.sub.3           &#34;  NO.sub.2                   &#34;     &#34;           &#34; 175-17989    &#34;  H      Cl Cl   &#34;     C.sub.2 H.sub.5                                     &#34; 118-12090    &#34;  &#34;      H  CH.sub.3                   &#34;     CH.sub.3    1 204-20691    &#34;  &#34;      &#34;  Cl   &#34;     &#34;           &#34; 219-22092    &#34;  OCH.sub.3           &#34;  H    &#34;     &#34;           &#34; 22093    Cl H      &#34;  Cl   &#34;     &#34;           &#34; 240-24294    H  Cl     H  H    CH.sub.3                         CH.sub.3    1 235-23895    &#34;  H      &#34;  Cl   C.sub.6 H.sub.5                         &#34;           &#34; 221-22396    &#34;  F      &#34;  H    CH.sub.3                         &#34;           &#34; 242-24497    &#34;  H      &#34;  F    &#34;     &#34;           &#34; 190-19398    &#34;  Cl     &#34;  CF.sub.3                   &#34;     &#34;           &#34; 196-19899    &#34;  H      &#34;  H    C.sub.6 H.sub.5                         &#34;           &#34; 239-241100   &#34;  H      H  F    &#34;                          ##STR27##  &#34; 218-220101   &#34;  H      H  CO.sub.2 CH.sub.3                   CH.sub.3                         CH.sub.3    &#34; 232-234102   &#34;  &#34;      &#34;  CF.sub.3                   &#34;     &#34;           &#34; 211-213103   &#34;  &#34;      &#34;  SO.sub.2 C.sub.6 H.sub.5                   &#34;     &#34;           &#34; 209-211104   &#34;  &#34;      &#34;  CN   &#34;     &#34;           &#34; 224-226105   NO.sub.2    &#34;      &#34;  F    &#34;     &#34;           &#34; 246-248106   CF.sub.3    &#34;      &#34;  Cl   &#34;     &#34;           &#34; 233-235107   H  F      Cl H    &#34;     &#34;           &#34; 245-247108   &#34;  Cl     H  Cl   &#34;     &#34;           &#34; 214-216109   NO.sub.2    H      &#34;  &#34;    &#34;     &#34;           &#34; 247-249110   H  Cl     &#34;  CH.sub.3                   &#34;     &#34;           &#34; 220-222111   &#34;  H      &#34;  C.sub.2 H.sub.5                   &#34;     &#34;           &#34; 210-211112   &#34;  &#34;      Cl Cl   &#34;     &#34;           &#34; 200-202113   &#34;  CF.sub.3           H  NO.sub.2                   &#34;     &#34;           &#34; 164-167114   &#34;  H      CF.sub.3              H    &#34;     &#34;           &#34; 203-207115   &#34;  Cl     H  CF.sub.3                   &#34;                          ##STR28##  &#34; 198-199116   Cl H      &#34;  Cl   &#34;     &#34;           &#34; 177-180117   H  CF.sub.3           &#34;  H    &#34;     CH.sub.3    &#34; 228-230118   &#34;  Cl     &#34;  CH.sub.3                   &#34;                          ##STR29##  &#34; 202-203119   &#34;  &#34;      &#34;  &#34;    &#34;                          ##STR30##  &#34; 164-169120   Cl H      H  CH.sub.3                   CH.sub.3                         CH.sub.3    1 243-244121   CH.sub.3    &#34;      CH.sub.3              H    &#34;     &#34;           &#34; 229-231122   Cl &#34;      H  Cl   &#34;     n-C.sub.4 H.sub.9                                     &#34; 172-173123   Cl &#34;      Cl H    &#34;     &#34;           &#34; 211-213124   Cl &#34;      Cl H    &#34;     &#34;           &#34; 250-252125   CF.sub.3    &#34;      CF.sub.3              &#34;    &#34;     &#34;           &#34; 230-233126   H  &#34;      H  C.sub.6 H.sub.5                   CH.sub.3                         CH.sub.3    &#34; 267-270127   &#34;  Cl     &#34;  CF.sub.3                   &#34;     n-C.sub.4 H.sub.9                                     &#34; 123-125128   NO.sub.2    H      &#34;  OCH.sub.3                   &#34;     CH.sub.3    &#34; &gt;260129   H  &#34;      &#34;  C.sub.6 H.sub.5                   &#34;     n-C.sub.4 H.sub.9                                     &#34; 147-150130   &#34;  &#34;      &#34;  &#34;    &#34;                          ##STR31##  &#34; 151-154131   &#34;  &#34;      &#34;  &#34;    &#34;                          ##STR32##  &#34; 209-211132   &#34;  &#34;      &#34;  i-C.sub.3 H.sub.7                   &#34;     n-C.sub.4 H.sub.9                                     &#34; 111-112133   &#34;  &#34;      &#34;  &#34;    &#34;                          ##STR33##  &#34; 125-130134   &#34;  &#34;      &#34;  CH.sub.2 C.sub.6 H.sub.5                   &#34;     CH.sub.3    &#34; 145-147135   &#34;  &#34;      &#34;  n-C.sub.3 H.sub.7                   &#34;     &#34;           &#34; 186-189136   &#34;  CH.sub.3           &#34;  Cl   &#34;     &#34;           &#34; 216-217137   &#34;  H      Cl CH.sub.3                   &#34;     &#34;           &#34; 194-196138   &#34;  Cl     H  CF.sub.3                   &#34;     C.sub.2 H.sub.5                                     &#34; 139-142139   &#34;  &#34;      &#34;  &#34;    &#34;     n-C.sub.6 H.sub.13                                     &#34;  98-100140   &#34;  CH.sub.3           Cl H    &#34;     CH.sub.3    &#34; 253-255141   Cl &#34;      H  &#34;    &#34;     &#34;           &#34; 222-223142   H  H      &#34;  CH.sub.2 C.sub.6 H.sub.5                   &#34;     i-C.sub.5 H.sub.11                                     &#34; 135-136143   &#34;  &#34;      &#34;  &#34;    &#34;     n-C.sub.4 H.sub.9                                     &#34; 124-125144   &#34;  Cl     &#34;  F    &#34;     CH.sub.3    &#34; 217-218145   &#34;  NO.sub.2           &#34;  Cl   &#34;     &#34;           &#34; 190-192146   CH.sub.3    H      H  Cl   CH.sub.3                         CH.sub.3    1 187-188147   H  F      &#34;  &#34;    &#34;     &#34;           &#34; 220-221148   CF.sub.3    H      &#34;  OCH.sub.3                   &#34;     &#34;           &#34; 201-202149   H  OCH.sub.3           H  OCH.sub.3                   CH.sub.3                         CH.sub.3    0 178-180150   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 231-232151   &#34;  H      Cl Cl   &#34;     C.sub.3 H.sub.7                                     0 93-95152   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 130-132153   &#34;  F      F  F    &#34;     CH.sub.3    &#34; 184-186154   &#34;  n-C.sub.6 H.sub.13           H  H    &#34;     &#34;           &#34; 152-154155   &#34;  Cl     CF.sub.3              &#34;    &#34;     &#34;           &#34; 265-267156   &#34;  H      F  CF.sub.3                   &#34;     &#34;           &#34; 247-250157   &#34;  F      H  CF.sub.3                   &#34;     &#34;           &#34; 202-204158   &#34;  H      Cl Cl   &#34;     C.sub.2 H.sub.5                                     &#34; 143-146159   &#34;  &#34;      &#34;  &#34;    &#34;     sec-C.sub.4 H.sub.9                                     0 78-80160   &#34;  Cl     NO.sub.2              HY   &#34;     CH.sub.3    &#34; 281-283161   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 253-255162   &#34;  H      Cl Cl   &#34;     sec-C.sub.4 H.sub.9                                     0 165-168163   &#34;     ##STR34##           H  H    &#34;     CH.sub.3    &#34; 208-210164   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 210-213165   Cl Cl     &#34;  Cl   &#34;     &#34;           0 181-183166   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 267-270167   H  &#34;      Cl &#34;    &#34;     &#34;           0 --168   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 183-184169   Cl &#34;      &#34;  H    &#34;     &#34;           0 264-266170   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 --171   &#34;  H      H  NO.sub.2                   &#34;     &#34;           1 202-204172   Cl H      H  NO.sub.2                   CH.sub.3                         CH.sub.3    0 197-199173   H  CH.sub.3           &#34;  F    &#34;     &#34;           &#34; 134-135174   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 233-235175   &#34;  F      &#34;  CH.sub.3                   &#34;     &#34;           0 160-161176   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 201-202177   &#34;  H      &#34;  OC.sub.6 H.sub.5                   &#34;     &#34;           0 152-153178   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 213-214179   &#34;  OCF.sub.3           &#34;  H    &#34;     &#34;           0 167-168180   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 248-251181   &#34;  Cl     &#34;  CF.sub.3                   &#34;                          ##STR35##  &#34; 187-188182   Cl H      &#34;  Cl   &#34;     &#34;           0 217-218183   H  Cl     &#34;  CF.sub.3                   &#34;     &#34;           &#34; 155-157184   Cl H      &#34;  Cl   &#34;     &#34;           1 248-250185   H  Cl     &#34;  CF.sub.3                    ##STR36##                         CH.sub.3    0 244-245186   &#34;  &#34;      &#34;  &#34;                    ##STR37##                         &#34;           &#34; 191-192187   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 156-157188   &#34;  H      Cl Cl   CH.sub.3                          ##STR38##  0 225-226189   &#34;  Cl     H  CF.sub.3                   C.sub.2 H.sub.5                         CH.sub.3    &#34; 101-102190   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 197-198191   &#34;  H      &#34;  Br   CH.sub.3                         &#34;           0 167-168192   &#34;  &#34;      Cl Cl   C.sub.2 H.sub.5                         &#34;           &#34; 150-151193   &#34;  &#34;      &#34;  &#34;    CH.sub.3                         CH.sub.2 CF.sub.3                                     &#34; 160-161194   &#34;  Cl     H  CF.sub.3                   &#34;     &#34;           &#34; 103-104195   &#34;  &#34;      &#34;  &#34;    n-C.sub.3 H.sub.7                         CH.sub.3    &#34; 112-113196   &#34;  H      Cl Cl   C.sub.2 H.sub.5                         &#34;           1 204-205197   &#34;  Cl     H  CF.sub.3                    ##STR39##                         &#34;           0 129-130198   H  Cl     H  CH.sub.3                   n-C.sub.3 H.sub.7                         CH.sub.3    1 160-161199   &#34;  &#34;      &#34;  &#34;                    ##STR40##                         &#34;           &#34; 188-189200   &#34;  H      &#34;  &#34;    CH.sub.2 C.sub.6 H.sub.5                         &#34;           0 102-103201   &#34;  COC.sub.6 H.sub.5           &#34;  NO.sub.2                   CH.sub.3                         &#34;           &#34; 209-210202   &#34;  H      &#34;  CF.sub.3                   i-C.sub.3 H.sub.7                         &#34;           &#34; 55-56203   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 134-135204   &#34;  Cl     &#34;  &#34;    &#34;     &#34;           0 94-95205   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 148-149206   &#34;  &#34;      &#34;  &#34;    i-C.sub.4 H.sub.9                         &#34;           0 78-79207   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 129-130208   &#34;  H      F  CH.sub.3                   CH.sub.3                         &#34;           0 116-119209   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 182-184210   &#34;  &#34;      H  CF.sub.3                   CH.sub.2 SC.sub.6 H.sub.5                         &#34;           0 149-150211   Cl H      H  CH.sub.3                    ##STR41##                         CH.sub.3    &#34; 100-101212   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 208-209213   H  &#34;      Cl H    i-C.sub.3 H.sub.7                         &#34;           0 218-220214   &#34;  &#34;      &#34;  &#34;    &#34;     &#34;           1 211-213__________________________________________________________________________ 
    
     
                       TABLE 2______________________________________4-alkoxy or 4-aryloxy-2-quinolinone(Ic) ##STR42##Comp.No.   R.sub.1       R.sub.2             R.sub.3                 R.sub.4                      R.sub.5                           R.sub.9    m.p. (°C.)______________________________________215   H     Cl    H   CF.sub.3                      CH.sub.3                           C.sub.2 H.sub.5                                      79-80216   &#34;     H     &#34;   &#34;    &#34;    n-C.sub.3 H.sub.7                                      --217   &#34;     &#34;     &#34;   &#34;    &#34;                            ##STR43## 57-58218   &#34;     &#34;     &#34;   &#34;    &#34;    i-C.sub.3 H.sub.7                                      103-104219   &#34;     &#34;     &#34;   &#34;    &#34;    n-C.sub.4 H.sub.9                                      31-32220   &#34;     &#34;     Cl  Cl   &#34;                            ##STR44## 192-193221   Cl    &#34;     H   &#34;    &#34;    &#34;          165-166222   H     Cl    &#34;   CF.sub.3                      &#34;    &#34;          157-158______________________________________ 
    
     
                                           TABLE 3__________________________________________________________________________4-amino-2-quinolinone(Id) ##STR45##Comp. No. R.sub.1    R.sub.2           R.sub.3              R.sub.4                   CH.sub.3                       NAB                      m.p.(°C.)__________________________________________________________________________223   H  Cl     H  CF.sub.3                   CH.sub.3                        ##STR46##               149-151224   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR47##               177-178225   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR48##               135-136226   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR49##               218-220227   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR50##               166-168228   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR51##               217-218229   &#34;  H      &#34;  Cl   C.sub.2 H.sub.5                        ##STR52##               164-166230   &#34;  &#34;      &#34;  CH.sub.3                   CH.sub.3                       &#34;                        158-161231   &#34;  Cl     &#34;  CF.sub.3                   &#34;                        ##STR53##               113-115232   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR54##               195-197233   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR55##               139-144234   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR56##               173-174235   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR57##               153-155236   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR58##               133-134237   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR59##               149-151238   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR60##               113-115239   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR61##               145-147240   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR62##               137-140241   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR63##               188-190242   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR64##               113-114243   H  Cl     H  CF.sub.3                   CH.sub.3                        ##STR65##               131-135244   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR66##               71-74245   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR67##               111-113246   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR68##               168-170247   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR69##               189-191248   &#34;  H      &#34;  F    &#34;                        ##STR70##               --249   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR71##               142-145250   &#34;  Cl     &#34;  CF.sub.3                   &#34;                        ##STR72##               66-68251   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR73##               171-173252   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR74##               157-159253   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR75##               163-167254   &#34;  H      &#34;  F    &#34;   NHCH.sub.3               146-150255   &#34;  &#34;      &#34;  &#34;    &#34;   NHC.sub.2 H.sub.5        --256   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR76##               151-153257   &#34;  Cl     &#34;  CF.sub.3                   &#34;                        ##STR77##               128-131258   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR78##               150-152259   &#34;  &#34;      &#34;  &#34;    &#34;   NHCH.sub.3               214-216260   &#34;  H      &#34;  &#34;    &#34;                        ##STR79##               196-198261   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR80##               137-140262   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR81##               160-161263   H  H      H  CF.sub. 3                   CH.sub.3                        ##STR82##               148-153264   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR83##               124-126265   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR84##               167-169266   &#34;  &#34;      &#34;  &#34;    &#34;   NHCH.sub.3267   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR85##               141-143268   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR86##               131-133269   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR87##               128-130270   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR88##               178-180271   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR89##               159-163272   &#34;  Cl     &#34;  &#34;    &#34;                        ##STR90##               92-93273   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR91##               89-92274   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR92##               179-181275   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR93##               199-202276   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR94##               71-74277   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR95##               173-174278   NO.sub.2    H      &#34;  F    &#34;                        ##STR96##               230-231279   H  &#34;      &#34;  CN   &#34;                        ##STR97##               159-162280   &#34;  &#34;      &#34;  CF.sub.3                   &#34;                        ##STR98##               132-135281   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR99##               --282   &#34;  F      Cl H    &#34;                        ##STR100##              254-256283   H  F      Cl H    CH.sub.3                        ##STR101##              190-192284   &#34;  Cl     H  Cl   &#34;                        ##STR102##              166-167285   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR103##              168-169286   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR104##              143-144267   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR105##              167-168288   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR106##              119-120289   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR107##              102-103290   NO.sub.2    H      &#34;  F    &#34;                        ##STR108##              231-233291   H  &#34;      &#34;  CF.sub.3                   &#34;                        ##STR109##              80-86292   &#34;  Cl     &#34;  Cl   &#34;                        ##STR110##              202-203293   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR111##              100-101294   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR112##              130-131295   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR113##              107-108296   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR114##              146-148297   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR115##              158-159298   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR116##              186-188299   &#34;  F      Cl H    &#34;                        ##STR117##              194- 196300   CF.sub.3    H      H  Cl   &#34;                        ##STR118##              174-175301   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR119##              205-207302   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR120##              208-209303   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR121##              142-143304   H  &#34;      &#34;  CF.sub.3                   &#34;                        ##STR122##              178-180305   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR123##              111-113306   NO.sub.2    H      H  Cl   CH.sub.3                        ##STR124##              224-229307   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR125##              191-200308   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR126##              217-220309   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR127##              249-250310   H  Cl     &#34;  &#34;    &#34;                        ##STR128##              193-194311   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR129##              162-163312   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR130##              175-176313   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR131##              142-143314   &#34;  F      Cl H    &#34;                        ##STR132##              259-262315   &#34;  H      H  CF.sub.3                   &#34;                        ##STR133##              190-193316   NO.sub.2    &#34;      &#34;  Cl   &#34;                        ##STR134##              215-217317   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR135##              150-153318   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR136##              216-218319   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR137##              201-203320   H  F      Cl H    &#34;                        ##STR138##              193-195321   NO.sub.2    H      H  Cl   &#34;                        ##STR139##              217-219322   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR140##              200-203323   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR141##              221-223324   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR142##              228-230325   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR143##              232-234326   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR144##              214-215327   H  F      Cl H    &#34;                        ##STR145##              257-260328   H  F      Cl H    CH.sub.3                        ##STR146##              &gt;260329   &#34;  H      H  CF.sub.3                   &#34;                        ##STR147##              113-116330   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR148##              105-107331   &#34;  Cl     &#34;  CH.sub.3                   &#34;                        ##STR149##              231-233332   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR150##              121-124333   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR151##              148-150334   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR152##              122-126335   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR153##              118-122336   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR154##              158-160337   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR155##              111-112338   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR156##              205-209339   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR157##              190-192340   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR158##              195-197341   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR159##              181-183342   &#34;  H      &#34;  CF.sub.3                   &#34;                        ##STR160##              135-137343   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR161##              135-137344   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR162##              169-171345   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR163##              164-166346   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR164##              180-183347   &#34;  Cl     &#34;  Cl   &#34;                        ##STR165##              118-120348   H  Cl     H  Cl   CH.sub.3                        ##STR166##              120-121349   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR167##              94-95350   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR168##              --351   &#34;  F      Cl H    &#34;                        ##STR169##              234-236352   &#34;  NO.sub.2           H  &#34;    &#34;                        ##STR170##              &gt;260353   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR171##              254-256354   &#34;  H      &#34;  CF.sub.3                   &#34;                        ##STR172##              205-208355   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR173##              181-185356   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR174##              159-164357   &#34;  t-C.sub.4 H.sub.9           &#34;  H    &#34;                        ##STR175##              217-219358   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR176##              182-184359   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR177##              219-220360   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR178##              243-245361   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR179##              185-186362   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR180##              141-143363   &#34;  H      &#34;  CF.sub.3                   &#34;                        ##STR181##              188-190364   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR182##              142-143365   &#34;  Cl     &#34;  Cl   &#34;                        ##STR183##              118-120366   &#34;  t-C.sub.4 H.sub.9           &#34;  H    &#34;   NHC.sub.2 H.sub.5        266-267367   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR184##              233-235368   &#34;  Cl     &#34;  CH.sub.3                   &#34;                        ##STR185##              112-116369   H  Cl     H  CH.sub.3                   CH.sub.3                        ##STR186##              168-170370   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR187##              164-167371   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR188##              201-203372   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR189##              186-191373   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR190##              208-209374   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR191##              154-155375   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR192##              178-182376   &#34;  t-C.sub.4 H.sub.9           &#34;  H    &#34;                        ##STR193##              175-176377   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR194##              253-254378   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR195##              231-233379   &#34;  Cl     &#34;  CH.sub.3                   &#34;                        ##STR196##              170-172380   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR197##              193-196381   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR198##              193-195382   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR199##              239-241383   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR200##              255-257384   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR201##              219-220385   &#34;  &#34;      &#34;  &#34;    &#34;   NHC.sub.2 H.sub.5        202-203386   &#34;  H      &#34;  C.sub.2 H.sub.5                   &#34;                        ##STR202##              168-169387   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR203##              186-187388   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR204##              169-171389   H  H      H  C.sub.2 H.sub.5                   CH.sub.3                        ##STR205##              188-190390   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR206##              80-82391   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR207##              114-115392   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR208##              163-164393   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR209##              143-145394   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR210##              137-139395   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR211##              181-183396   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR212##              108-109397   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR213##              99-100398   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR214##              148-150399   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR215##              150-153400   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR216##              114-116401   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR217##              180-182402   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR218##              139-140403   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR219##              148-150404   &#34;  Cl     &#34;  CF.sub.3                   &#34;                        ##STR220##              127-128405   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR221##              192-194406   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR222##              228-231407   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR223##              171-172408   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR224##              203-205409   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR225##              244-246410   H  Cl     H  CF.sub.3                   CH.sub.3                        ##STR226##              226-228411   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR227##              332-335412   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR228##              173-175413   &#34;  &#34;      &#34;  CH.sub.3                   &#34;                        ##STR229##              216-220414   &#34;  &#34;      &#34;  &#34;    &#34;   NHCH.sub.3               250-252415   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR230##              221-222416   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR231##              209-211417   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR232##              210-212418   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR233##              141-160419   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR234##              305-308420   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR235##              195-197421   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR236##              141-144422   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR237##              155-156423   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR238##              194-195424   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR239##              165-167425   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR240##              196-198426   &#34;  t-C.sub.4 H.sub.9           &#34;  &#34;    &#34;                        ##STR241##              231-232427   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR242##              235-236428   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR243##              161-163429   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR244##              187-189__________________________________________________________________________ 
    
     
         __________________________________________________________________________430   H  t-C.sub.4 H.sub.9           H  H    CH.sub.3                        ##STR245##              172-173431   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR246##              208-210432   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR247##              217-218433   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR248##              253-255434   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR249##              236-238435   &#34;  Cl     &#34;  CF.sub.3                   &#34;                        ##STR250##              122-124436   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR251##              167-169437   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR252##              202-204438   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR253##              204-206439   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR254##              184-186440   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR255##              126-129441   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR256##              173-174442   CF.sub.3    H      &#34;  Cl   &#34;                        ##STR257##              206-208443   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR258##              168-170444   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR259##              165-167445   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR260##              184-187446   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR261##              178-179447   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR262##              173-175448   H  BR     CF.sub.3              H    &#34;                        ##STR263##              231-233449   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR264##              213-215450   H  BR     CF.sub.3              H    CH.sub.3                        ##STR265##              258-259451   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR266##              261-263452   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR267##              275-278453   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR268##              232-234454   CF.sub.3    H      H  Cl   &#34;                        ##STR269##              189-190455   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR270##              235-238456   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR271##              225-226457   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR272##              186-188458   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR273##              174-176459   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR274##              218-219460   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR275##              231-235461   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR276##              208-210462   H  Cl     CF.sub.3              H    &#34;                        ##STR277##              239-240463   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR278##              223-226464   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR279##              249-250465   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR280##              259-260466   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR281##              217-222467   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR282##              232-234468   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR283##              192-194469   &#34;  H      &#34;  &#34;    &#34;                        ##STR284##              233-235470   H  H      CF.sub.3              H    CH.sub.3                        ##STR285##              238-240471   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR286##              266-268472   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR287##              234-236473   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR288##              251-252474   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR289##              238-239475   &#34;  &#34;      Cl Cl   &#34;                        ##STR290##              110-111476   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR291##              162-164477   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR292##              190-198478   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR293##              133-135479   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR294##              112-114480   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR295##              201-203481   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR296##              173-174482   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR297##              175-176483   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR298##              172-173484   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR299##              150-151485   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR300##              153-155486   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR301##              85-86487   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR302##              197-198488   &#34;  &#34;      &#34;  &#34;    &#34;   NHCH.sub.3               213-215489   CF.sub.3    &#34;      H  &#34;    &#34;                        ##STR303##              177-178490   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR304##              211-213491   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR305##              133-135492   CF.sub.3    H      H  Cl   CH.sub.3                        ##STR306##              209-212493   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR307##              222-224494   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR308##              160-161495   Cl &#34;      &#34;  &#34;    &#34;                        ##STR309##              179-180496   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR310##               205497   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR311##              216-217498   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR312##              232-234499   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR313##              175-177500   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR314##              164-165501   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR315##              184-185502   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR316##              176-178503   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR317##              190-192504   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR318##              235-237505   H  Cl     CF.sub.3              H    &#34;                        ##STR319##              239-242506   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR320##              285-286507   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR321##              167-173508   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR322##              192-193509   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR323##              211-212510   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR324##              245-247511   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR325##              235-239512   Cl H      H  Cl   &#34;                        ##STR326##              170-173513   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR327##              149-150514   CF.sub.3    &#34;      &#34;  &#34;    &#34;                        ##STR328##              223-226515   H  Cl     H  CH.sub.3                   NHCH.sub.3                       266-268516   &#34;  H      &#34;  C.sub.2 H.sub.5                   &#34;   &#34;                        168-170517   &#34;  OCH.sub.3           &#34;  H    &#34;   &#34;                        248-250518   CF.sub.3    H      &#34;  Cl   &#34;   &#34;                        270-274519   H  H      &#34;  &#34;    &#34;&#34;  211-213520   &#34;  Cl     CF.sub.3              H    &#34;   &#34;                        275-277521   &#34;  H      &#34;  &#34;    &#34;                        ##STR329##              277-279522   &#34;  CF.sub.3           H  H    &#34;                        ##STR330##              235-237523   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR331##              225-227524   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR332##              254-257525   &#34;  Cl     &#34;  CH.sub.3                   &#34;                        ##STR333##              197-198526   &#34;  &#34;      CF.sub.3              H    &#34;                        ##STR334##              111-116527   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR335##              276-277528   Cl H      H  CH.sub.3                   &#34;                        ##STR336##              164-166529   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR337##              215-216530   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR338##              184-185531   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR339##              207-208532   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR340##              182-185533   CH.sub.3    H      CH.sub.3              H    &#34;                        ##STR341##              140-142534   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR342##              145-146535   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR343##              213-214536   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR344##              220-222537   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR345##              117-120538   CH.sub.3    H      CH.sub.3              H    CH.sub.3                        ##STR346##              203-205539   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR347##              182-184540   H  CF.sub.3           H  &#34;    &#34;                        ##STR348##              205-210541   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR349##              137-138542   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR350##              124-126543   &#34;  H      &#34;  I-C.sub.3 H.sub.7                   &#34;                        ##STR351##              126-128544   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR352##              154-155545   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR353##              107-108546   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR354##              114-115547   NO.sub.2    &#34;      &#34;  Cl   &#34;                        ##STR355##              202-203548   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR356##              258-259549   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR357##              251- 254550   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR358##              246-248551   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR359##              242-245552   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR360##              206-208553   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR361##              242-244554   Cl &#34;      Cl H    &#34;                        ##STR362##              192-195555   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR363##              124-125556   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR364##              128-130557   &#34;  &#34;      H  CH.sub.3                   &#34;                        ##STR365##              213-214558   NO.sub.2    &#34;      &#34;  OCH.sub.3                   &#34;                        ##STR366##              162-165559   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR367##              175-176__________________________________________________________________________ 
    
     
         __________________________________________________________________________560   NO.sub.2    H      H  OCH.sub.3                   CH.sub.3                        ##STR368##              135-138561   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR369##              178-179562   &#34;  &#34;      &#34;  Cl   &#34;                        ##STR370##              219-220563   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR371##              266-269564   H  &#34;      &#34;  C.sub.6 H.sub.5                   &#34;                        ##STR372##              142-144565   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR373##              134-136566   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR374##              168-169567   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR375##              198-200568   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR376##              156-158569   &#34;  &#34;      &#34;  &#34;    &#34;   NHCH.sub.3               196-198570   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR377##              178-180571   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR378##              182-183572   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR379##              200-202573   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR380##              127-133574   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR381##              193-196575   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR382##              170-171576   &#34;  CH.sub.3           &#34;  CH.sub. 3                   &#34;                        ##STR383##              185-186577   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR384##              108-111578   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR385##              128-130579   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR386##              182-183580   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR387##              85-87581   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR388##              163-164582   H  CH.sub.3           H  CH.sub.3                   CH.sub.3                        ##STR389##              150-151583   &#34;  Cl     &#34;  CF.sub.3                   &#34;                        ##STR390##              166-174584   H  &#34;      &#34;  &#34;    &#34;                        ##STR391##              164-167585   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR392##              157-161586   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR393##              158-160587   &#34;  H      &#34;  CH.sub.2 C.sub.6 H.sub.5                   &#34;                        ##STR394##              132-134588   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR395##              97-98589   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR396##               98-100590   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR397##              146-147591   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR398##              131-132592   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR399##              138-140593   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR400##              119-120594   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR401##              153-154595   &#34;  CH.sub.3           &#34;  CH.sub.3                   &#34;                        ##STR402##              222-223596   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR403##              237-239597   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR404##              223-226598   Cl H      Cl H    &#34;                        ##STR405##              205-207599   NO.sub.2    &#34;      H  OCH.sub.3                   &#34;                        ##STR406##              210-213600   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR407##              200-201601   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR408##              133-134602   H  Cl     H  CF.sub.3                   CH.sub.3                        ##STR409##              216-217603   &#34;  H      &#34;  n-C.sub.3 H.sub.7                   &#34;                        ##STR410##              168-170604   H  &#34;      &#34;  &#34;    &#34;                        ##STR411##              174-176605   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR412##              127-129606   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR413##              134-136607   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR414##              106-108608   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR415##              104-105609   &#34;  CH.sub.3           &#34;  Cl   &#34;                        ##STR416##              173-175610   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR417##              103-105611   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR418##              149-150612   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR419##              248-251613   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR420##              147-150614   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR421##              161-162615   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR422##              231-233616   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR423##              128-130617   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR424##              135-136618   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR425##              171-172619   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR426##              236-238620   &#34;  Cl     &#34;  CF.sub.3                   &#34;                        ##STR427##              214-217621   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR428##              228-231622   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR429##              201-202623   Cl H      Cl H    CH.sub.3                        ##STR430##              187-188624   H  CH.sub.3           Cl &#34;    &#34;                        ##STR431##              252-255625   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR432##              228-231626   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR433##              255-258627   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR434##              248-251628   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR435##              263-265629   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR436##              231-234630   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR437##              257-258631   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR438##              295-296632   Cl CH.sub.3           H  &#34;    &#34;                        ##STR439##              198-199633   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR440##              217-218634   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR441##              209-210635   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR442##              189-190636   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR443##              198-199637   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR444##              219-220638   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR445##              201-202639   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR446##              224-225640   H  Cl     &#34;  F    &#34;                        ##STR447##              168-170641   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR448##              148-150642   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR449##              244-247643   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR450##              138-140644   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR451##              235-240645   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR452##              169-170646   H  Cl     H  F    CH.sub.3                        ##STR453##              198-200647   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR454##              151-153648   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR455##              150-157649   CH.sub.3    H      &#34;  Cl   &#34;                        ##STR456##              113-115650   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR457##               131651   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR458##              178-181652   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR459##              187-189653   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR460##              105-107654   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR461##              133-134655   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR462##              174-176656   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR463##              162-163657   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR464##              121-122658   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR465##              137-138659   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR466##               142660   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR467##              98-99661   H  F      &#34;  Cl   &#34;                        ##STR468##              192-194662   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR469##              164-165663   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR470##              211-215664   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR471##              194-197665   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR472##              211-213666   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR473##              123-125667   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR474##              210-211668   H  F      H  Cl   CH.sub.3                        ##STR475##              140-145669   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR476##              126-127670   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR477##              194-197671   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR478##              205-206672   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR479##              204-205673   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR480##              164-165674   &#34;  &#34;      Cl H    &#34;                        ##STR481##              270-280675   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR482##              288-290676   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR483##              &gt;260677   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR484##              265-270678   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR485##              &gt;300679   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR486##              275-278680   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR487##              297-300681   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR488##              &gt;300682   CF.sub.3    H      H  OCH.sub.3                   &#34;                        ##STR489##              232-233683   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR490##              204-206684   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR491##              231-232685   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR492##              189-190686   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR493##              232-234687   H  Cl     H  CF.sub.3                   CH.sub.3                        ##STR494##              204-206688   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR495##              194-195689   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR496##              143-144690   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR497##              166-168691   &#34;  OCH.sub.3           &#34;  OCH.sub.3                   &#34;                        ##STR498##              177-178692   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR499##              178-180693   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR500##              226-228694   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR501##              156-157695   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR502##              --696   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR503##              233-234697   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR504##              140-141698   &#34;  Cl     NO.sub.2              H    &#34;   &#34;                        235-237699   &#34;  H      H  F    &#34;                        ##STR505##              116-118700   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR506##              121-123701   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR507##               98-100702   &#34;     ##STR508##           &#34;  H    &#34;                        ##STR509##              79-80703   H     ##STR510##           H  H    CH.sub.3                        ##STR511##              250-252704   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR512##              252-254705   Cl Cl     &#34;  Cl   &#34;                        ##STR513##              140-142706   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR514##              231-233707   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR515##              237-239708   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR516##              126-128709   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR517##              199-200710   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR518##              144-145711   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR519##              198-200712   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR520##              148-150713   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR521##              251-253714   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR522##              205-207715   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR523##              261-263716   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR524##              218-219717   H  &#34;      H  H    C.sub.6 H.sub.5                        ##STR525##              285-286718   &#34;  NO.sub.2           &#34;  Cl   CH.sub.3                        ##STR526##              155-157719   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR527##              210-212720   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR528##              88-90721   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR529##              166-168722   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR530##              208-210723   H  H      H  H    C.sub.6 H.sub.5                        ##STR531##              293-294724   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR532##              257-258725   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR533##              295-296726   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR534##              &gt;300727   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR535##              297-298728   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR536##              238-240729   &#34;  NO.sub.2           &#34;  Cl   CH.sub.3                        ##STR537##              219-220730   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR538##              168-170731   &#34;  H      &#34;  H    C.sub.6 H.sub.5                        ##STR539##              293-294732   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR540##              281-282733   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR541##              210-212734   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR542##              187-188735   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR543##              284-285736   &#34;  Cl     Cl Cl   CH.sub.3                        ##STR544##              145-147737   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR545##              135-136738   &#34;  H      H  F    &#34;                        ##STR546##              170-173739   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR547##              110-112740   Cl Cl     Cl H    &#34;                        ##STR548##              &gt;260741   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR549##              166-168742   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR550##              220-222743   Cl Cl     Cl H    CH.sub.3                        ##STR551##              &gt;260744   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR552##              234-236745   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR553##              250(dec)746   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR554##              154-156747   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR555##              180(dec)748   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR556##              226-228749   &#34;  &#34;      H  Cl   &#34;                        ##STR557##              228-230750   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR558##              204-206751   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR559##              246-247752   H  CH.sub.3           &#34;  F    &#34;                        ##STR560##              166-167753   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR561##              123-125754   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR562##              260-261755   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR563##              220-222756   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR564##              127-129757   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR565##               97-100758   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR566##              115-117759   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR567##              219-220760   &#34;  F      &#34;  CH.sub.3                   &#34;                        ##STR568##              136-137761   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR569##              oil762   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR570##              169-170763   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR571##              oil764   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR572##              174-176765   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR573##              203-204__________________________________________________________________________ 
    
     
         __________________________________________________________________________766   H  F      H  CH.sub.3                   CH.sub.3                        ##STR574##              209-210767   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR575##              147-148768   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR576##              154-155769   &#34;  H      &#34;  OC.sub.6 H.sub.5                   &#34;                        ##STR577##              163-165770   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR578##              173-175771   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR579##              177-179772   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR580##              144-145773   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR581##              202-204774   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR582##              165-167775   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR583##              182-184776   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR584##              135-136777   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR585##              243-245778   NO.sub.2    &#34;      &#34;  Cl   &#34;                        ##STR586##              205-207779   H  Cl     &#34;  CF.sub.3                   C.sub.6 H.sub.5                        ##STR587##              164-165780   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR588##              194-195781   &#34;  &#34;      &#34;  &#34;    CH.sub.3                        ##STR589##              236-240782   NO.sub.2    H      &#34;  Cl   &#34;   &#34;                        250-260783   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR590##              200-202784   H  Cl     &#34;  CF.sub.3                   C.sub.6 H.sub.5                        ##STR591##              132-133785   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR592##              154-155786   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR593##              222-223787   NO.sub.2    H      &#34;  Cl   CH.sub.3                        ##STR594##              230-233788   H  Cl     H  CF.sub.3                   CH.sub.3                        ##STR595##              169-170789   &#34;  H      &#34;  H    &#34;                        ##STR596##              268-270790   &#34;  &#34;      Cl Cl   &#34;                        ##STR597##              213-215791   &#34;  &#34;      H  CF.sub.3                   &#34;                        ##STR598##              225-227792   &#34;  &#34;      Cl Cl   &#34;                        ##STR599##              181-183793   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR600##              224-225794   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR601##              192-193795   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR602##              234-235796   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR603##              224-225797   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR604##              205-206798   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR605##              200-201799   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR606##              242-243800   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR607##              245-246801   &#34;  Cl     H  CF.sub.3                   &#34;                        ##STR608##              193-195802   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR609##              183-185803   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR610##              172-173804   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR611##              143-144805   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR612##              160-162806   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR613##              179-181807   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR614##              171-173808   H  Cl     H  CF.sub.3                   CH.sub.3                        ##STR615##              171-173809   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR616##              196-197810   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR617##              222-224811   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR618##              240-241812   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR619##              212-213813   &#34;  H      Cl Cl   &#34;   &#34;                        215-217814   Cl &#34;      H  &#34;    &#34;                        ##STR620##              234-235815   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR621##              224-225816   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR622##              208-209817   &#34;         &#34;  &#34;    &#34;                        ##STR623##              210-211818   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR624##              205-206819   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR625##              240-241820   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR626##              263-265821   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR627##              160-162822   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR628##              210-211823   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR629##              160-162824   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR630##              243-245825   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR631##              268-270826   &#34;         &#34;  &#34;    &#34;                        ##STR632##              250-252827   H  H      Cl Cl   CH.sub.3                        ##STR633##              284-286828   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR634##              &gt;260829   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR635##              289-290830   &#34;  CH.sub.3           H  &#34;    &#34;                        ##STR636##              225-227831   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR637##              228-229832   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR638##              242-243833   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR639##              221-222834   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR640##              &gt;260835   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR641##              268-269836   &#34;  Cl     &#34;  CF.sub.3                   &#34;                        ##STR642##              182-183837   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR643##              171-172838   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR644##              198-199839   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR645##              205-207840   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR646##              183-185841   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR647##              190-191842   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR648##              172-174843   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR649##              208-209844   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR650##              119-120845   &#34;  &#34;      &#34;  Cl   &#34;                        ##STR651##              204-205846   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR652##              253-254847   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR653##              227-229848   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR654##              215-216849   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR655##              191-192850   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR656##              228-229851   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR657##              249-250852   H  Cl     H  Cl   CH.sub.3                        ##STR658##              244-245853   &#34;  &#34;      &#34;  CF.sub.3                   C.sub.2 H.sub.5                        ##STR659##              154-155854   &#34;  &#34;      &#34;  CH.sub.3                   CH.sub.3                        ##STR660##              220-221855   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR661##              &gt;260856   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR662##              244-246857   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR663##              249-250858   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR664##              197-199859   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR665##              &gt;260860   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR666##              228-229861   &#34;  H      &#34;  C.sub.2 H.sub.5                   &#34;                        ##STR667##              162-163862   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR668##              164-165863   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR669##              231-232864   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR670##              144-145865   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR671##              144-145866   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR672##              142-143867   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR673##              163-164868   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR674##              182-184869   &#34;  Cl     &#34;  CF.sub.3                   C.sub.2 H.sub.5                        ##STR675##              84-85870   &#34;  H      &#34;  &#34;    CH.sub.3                        ##STR676##              165-166871   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR677##              --872   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR678##              169-170873   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR679##              202-203874   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR680##              158-159875   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR681##              190-191876   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR682##              233-234877   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR683##              168-169878   H  H      H  CF.sub.3                   CH.sub.3                        ##STR684##              162-163879   &#34;  F      &#34;  CH.sub.3                   &#34;                        ##STR685##              162-163880   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR686##              156-157881   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR687##              163-164882   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR688##              132-133883   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR689##              144-145884   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR690##              149-150885   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR691##              164-165886   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR692##              169-170887   &#34;  H      &#34;  C.sub.6 H.sub.5                   &#34;                        ##STR693##              167-168888   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR694##              209-211889   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR695##              206-207890   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR696##              204-206891   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR697##              161-162892   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR698##              183-186893   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR699##              174-176894   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR700##              190-192895   Cl Cl     &#34;  Cl   &#34;                        ##STR701##              217-218896   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR702##              198-199897   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR703##              215-218898   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR704##              193-195899   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR705##              282-285900   H  H      &#34;  i-C.sub.3 H.sub.7                   &#34;                        ##STR706##              186-189901   &#34;  &#34;      &#34;  CH.sub.2 C.sub.6 H.sub.5                   &#34;                        ##STR707##              110-114902   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR708##              156-157903   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR709##              199-200904   H  H      H  CH.sub.2 C.sub.6 H.sub.5                   CH.sub.3                        ##STR710##              128-130905   NO.sub.2    &#34;      &#34;  Cl   &#34;                        ##STR711##              238-239906   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR712##              267-268907   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR713##              210-213908   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR714##              240-242909   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR715##              180-182910   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR716##              217-219911   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR717##              293-295912   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR718##              228-230913   H  &#34;      Cl &#34;    &#34;                        ##STR719##              224-225914   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR720##              216-217915   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR721##              222-223916   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR722##              204-205917   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR723##              262-263918   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR724##              271-274919   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR725##              254-256920   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR726##              &gt;260921   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR727##              &gt;260922   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR728##              260-261923   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR729##              228-230924   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR730##              &gt;260925   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR731##              &gt;300926   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR732##              240-242927   &#34;  &#34;      &#34;  Cl   &#34;                        ##STR733##              232-233928   &#34;  Cl     H  CF.sub.3                   C.sub.2 H.sub.5                       &#34;                        113-115929   &#34;  H      &#34;  &#34;    CH.sub.3                       &#34;                        151-152930   Cl Cl     Cl H    CH.sub.3                        ##STR734##              272-273931   H  F      H  CF.sub.3                   &#34;   &#34;                        156-157932   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR735##              125-130933   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR736##              160-161934   &#34;  H      &#34;  F    &#34;                        ##STR737##              209-210935   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR738##              219-220936   &#34;  &#34;      Cl Cl   C.sub.2 H.sub.5                        ##STR739##              238-239937   &#34;  Cl     H  CF.sub.3                   n-C.sub.3 H.sub.7                       &#34;                        159-160938   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR740##              165-167939   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR741##              --940   &#34;  &#34;      &#34;  &#34;    CH.sub.3                        ##STR742##              &gt;260941   &#34;  H      &#34;  &#34;    &#34;                        ##STR743##              &gt;260942   &#34;  &#34;      &#34;  &#34;    i-C.sub.3 H.sub.7                        ##STR744##              103-104943   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR745##              130-131944   &#34;  Cl     &#34;  &#34;    &#34;                        ##STR746##              129-130945   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR747##              163-164946   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR748##              119-121947   &#34;  &#34;      &#34;  &#34;    &#34;   &#34;                        98-100948   &#34;  &#34;      &#34;  &#34;    i-C.sub.4 H.sub.9                        ##STR749##              144-146949   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR750##              134-137950   &#34;  H      F  CH .sub.3                   CH.sub.3                       &#34;                        211-213951   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR751##              208-210952   &#34;  &#34;      &#34;  &#34;    &#34;                        ##STR752##              237-238953   Cl &#34;      H  &#34;                        ##STR753##              --__________________________________________________________________________ 
    
     EXAMPLE 1 
     3-Acetyl-4-methylthio-2-quinolinone(1) 
     N-Phenyl-α-(bismethylthioylidene)acetoacetamide(28.1 g, 0.1 mol) was heated and refluxed for 2hr in solvent of dichlorobenzene(300 ml) untill the evolution of methylmercaptane ceased. 
     The reaction progress was determined by chromatography. When the reaction was completed, the reaction mixture was cooled, and then the precipitate was filtered to give the desired product(19.1 g, yield: 82 % ). 
       1  H NMR (DMSO-d 6 ): δ10.7(s, 1H),8.2˜7.15(m,4H),2.65(s,3H),2.53(s,3H). 
     EXAMPLE 2 
     3-Acetyl-7-methoxy-4-methylthio-2-quinolinone (2) 
     N-(m-Anisyl)-α-(bismethylthioylidene)acetoacetamide(3.1 g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product(2.1g, yield: 82%). 
       1  H NMR(CDCl 3 ): δ10.49(s, 1H), 8.18˜6.68(s, 3H), 3.8(s, 3H), 2.64(s, 3H), 2.53(s, 3H). 
     EXAMPLE 3 
     3-Acetyl-8-chloro-4-methylthio-2-quinolinone (3) 
     N-(2-Chlorophenyl)-α-(bismethylthioylidene)acetoacetamide (3.2g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (2.2g, yield: 86%). 
       1  H NMR (DMSO-d 6  ): δ8.2˜7.25(m, 3H), 4.5˜3.0(brs), 2.67(s, 3H), 2.59(s, 3H). 
     EXAMPLE 4 
     3-Acetyl-5,8-dichloro-4-methylthio-2-quinolinone (4) 
     N-(2,5-Dichlorophenyl)-α-(bismethylthioylidene)acetoacetamide (3.5g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (2.0g, yield:68%). 
       1  H NMR(DMSO-d 6  +CDCl 3 ): δ7.7 (d, J=9.0, 1H),7.27(d, J=9.0, 1H), 2.64(s,3H), 2.52(s,3H). 
     EXAMPLE 5 
     3-Acetyl-6-methoxy-4-methylthio-2-quinolinone (5) 
     N-(p-Anisyl)-α-(bismethylthioylidene)acetoacetamide (3.1 g, 0.01 mol) was used, but the reaction was camm out as the above process of example 1 to obtain the desired product (1.9g, yield: 74%). 
       1  H NMR(DMSO-d 6 ): δ10.68(s,1H),7.93˜6.95(m,3H),3.83(s,3H), 2.63(s,3H),2.59(s,3H). 
     EXAMPLE 6 
     3-Acetyl-6-fluoro-4-methylthio-2-quinolinone (7) 
     N-(4-Fluorophenyl)-α-(bismethylthioylidene)acetoacetamide (3.0g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (2.3g, yield: 95%). 
       1  H NMR(DMSO-d 6  +CDCl3): δ8.1˜7.2(m,3H),2.62(s,3H), 2.55(s, 3H). EXAMPLE 7 
     3-Acetyl-8-fluoro-4-methylthio-2-quinolinone (8) 
     N-(2-Fluorophenyl)-α-(bismeth ylthioylidene)butyrylacetami de (3.0g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (2.0g, yield: 85%). 
       1  H NMR(DMSO-d 6  +CDCl 3 ): δ6.13˜7.1(m,3H),2.65(s,3H),2.57(s,3H). 
     EXAMPLE 8 
     3-Butyryl-8-chloro-4-methylthio-2-quinolinone (9) 
     N-(2-Chlorophenyl)-α-(bismethyl thioylidene)butyrylacetamide (3.4g, 0.01 mol) was used, but the reaction was carded out as the above process of example 1 to obtain the desired product (2.5g, yield: 895). 
       1  H NMR(CDCl 3 ): δ8.7(s,1H), 8.52˜8.05(m,1H),7.47˜6.75(m,3H), 2.760, (t,J=7.0, 2H),2.45(s,6H), 1.72(m,2H), 2.45(s,6H), 1.72(m,2H), 0.95(t,J=7.0, 3H). 
     EXAMPLE 9 
     3-Acetyl-8-methyl-8-methylthio-2-quinolinone (11) 
     N-(o-Tolyl)-α-(bismethyl thioylidene)acetoacetamide (3.0g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (2.1g, yield: 88%). 
       1  H NMR(DMSO-d 6 ): δ15.6(s,1H), 8.06˜7.3(m,3H),2.93(s,3H), 2.69(s, 3H), 2.65(s,3H). 
     EXAMPLE 10 
     3-Benzoyl-8-chloro-4-methylthio-2-quinolinone (12) 
     N-(2-Chlorophenyl)-α-(bismethylthioylidene) benzoylacetamide (3.8g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (2.6g, yield : 81%). 
       1  H NMR(DMSO-d 6 , CDCl 3 ): δ8.3˜7.2(m,8H),2.65(s,3H). 
     EXAMPLE 11 
     3-Acetyl-6-chloro-8-trifluoroethy14-methylthio-2-quinolinone (13) 
     N-(4-Chloro-2-trifluoromethylphenyl)-α-(bismethylthioylidene) acetoacetamide (3.8 g, 0.01 mol) was used, but the reaction was carded out as the above process of example 1 to obtain the desired product (2.3g, yield: 71%). 
       1  H NMR(CDCl 3  +DMSO-d 6  ): δ8.3(s,1H), 8.12(s,3H), 2.67(s,3H). 
     EXAMPLE 12 
     3-Acetyl-8-methoxycarbonyl-4-methylthio-2-quinolinone (16) 
     N -(2-Methoxycarbonylphenyl)- α-(bismethylthioylidene)acetoacetamide (3.4g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (2.8g, yield: 99%). 
       1  H NMR(DMSO-d 6  +CDCl 3 ): δ2.6(s,3H), 3.27(s,3H), 4.03(s,3H), 7.4˜8.6(m,3H). 
     EXAMPLE 13 
     3-Acetyl-6-nitro-4-methylthio-2-quinolinone (20) 
     N-(4-Nitrophenyl)-α-(bismethylthioylidene)acetoacetamide (3.3g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (2.1 g, yield: 80% ). 
       1  H NMR(DMSO-d 6  +CDCl 3 ): δ2.57(s,3H), 2.66(s,3H),8.0˜8.9(m,4H). 
     EXAMPLE 14 
     3-Acetyl-6-chloro-7-nitro-4-methylthio-2-quinolinone (21) 
     N-(3-Nitro-4-chlorophenyl)-α-(bismethyl thioylidene)acetoacemmide (3.6g, 0.01 mol) was used, but the reaction was carded out as the above process of example to obtain the desired product (1.8g, yield: 61%). 
       1  H NMR(DMSO-d 6  +CDCl 3 ): δ2.43(s,3H), 2.7(s,3H), 7.73˜8.13(m,2H), 11.4(s,1H). 
     EXAMPLE 15 
     3-Acetyl-8-cyano-4-methylthio-2-quinolinone(22) 
     N-(2-Cyanophenyl)-α-(bismethylthioylidene)acetoacetamide (3.1g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (1 .8g, yield: 73%). 
       1  H NMR(DMSO-d 6  +CDCl 3 ): δ2.13(s,3H), 2.7(s,3H), 7.6˜8.7(m,3H). 
     EXAMPLE 16 
     3-Acetyl-6-chloro-8-trifluoromethyl-4-(t-butylbenzylthio)-2-quinolinone (23) 
     N-(4-Chloro-2-trifluo romet hylph enyl) -α-[bis-(t-butylbenzylthio)ylidene]acetoacetamide (6.3g, 0.01 mol) was used, but the reaction was carded out as the above process of example 1 to obtain the desired product (2.5g, yield: 54%). 
       1  H NMR(DMSO-d 6  +CDCl 3 ): δ1.27(s,9H), 2.73(s,3H), 4.6(s,2H), 7.35(s,4H), 7.95(d,1H), 8.52(d,1H). 
     EXAMPLE 17 
     3-Acetyl-6-t-butyl-4-methylthio-2-quinolinone (24) 
     N-(4-t-Butylphenyl)-α-(bismethylthioylidene)acetoacetamide (3.4g, 0.01  mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (2.3g, yield: 84%). 
       1  H NMR(DMSO-d 6  +CDCl 3 ): δ1.37(s,9H), 2.6(s,3H), 2.63(s,3H), 7.73(d,2H), 8.23(s,1H), 10.83(s,1H). 
     EXAMPLE 18 
     3-Acetyl-5,6,7,8-tetrachloro-4-methylthio-2-quinolinone (27) 
     N-(2,3,4,5-Tetrachlorophenyl)-α-(bismethylthioylidene)acetoacetamide (3.5g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (2.6g, yield: 74%). 
       1  H NMR(DMSO-d 6  +CDCl 3 ): δ2.43(s,3H), 2.66(s,3H), 7.96(s,1H). 
     EXAMPLE 19 
     3-Acetyl-8-trifluommethyl-4-methylthio-2-quinolinone (29) 
     N-(2-Tfifiuoromethylphenyl)-α-(bismethylthioylidene)acetoacetamide (3.5 g, 0.01mol) was used, but the reaction was carried out as the above process of example to obtain the desired product (1 .9g, yield: 65%). 
       1  H NMR(DMSO-d 6  +CDCl 3 ): δ2.6(s,3H), 2.7(s,3H), 8.06(m,1H),8.63(m,1H). 
     EXAMPLE 20 
     3-Acetyl-8-fluoro-8-trifluoromethyl-4-methylthio-2-quinolinone (33) 
     N-(4-Fluoro-2-trifluoromethylphenyl)-α-(bismethylthioylidene)acetoacet amide (3.7g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (2.5g, yield: 83%). 
       1  H NMR(CDCl 3 ): δ2.7(s,3H), 2.97(s,3H), 7.73˜8.16(m,1H), 15.63(s,1H). 
     EXAMPLE 21 
     3-Acetyl-7-fluoro-8-trifluoromethyl-4-methylthio-2-quinolinone (34) 
     N-(2 -Trifluoromethyl-3 -fluorophenyl)-α- (bismethylthioylidene)acetoacet amide (3.7g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (2.2g, yield: 73%). 
       1  H NMR(CDCl 3 ): δ2.72(s,3H), 2.93(s,3H), 7.1˜7.68(m,1H), 7.83˜8.1(m,2H). 
     EXAMPLE 22 
     3-Acetyl-6-bromo-8-trifluoromethyl-4-methylthio-2-quinolinone (35) 
     N-4-Bromo-8-trifluoromethyl-α-(bismethylthioylidene)acetoacetarnide (4.3g, 0.01 mol) was used, but the reaction was carried out as the above process of example to obtain the desired product (2.5g, yield: 67%). 
       1  H NMR(CDCl 3 ): δ2.7(s,3H), 2.93(s,3H), 8.1(s,1H), 8.53(s,1H), 15.6(s,1H). 
     EXAMPLE 23 
     3-Acetyl-6-chloro-7-trifluoromethyl-4-methylthio-2-quinolinone (36) 
     N-(3-Trifluoromethyl)-α-(bismeth ylthioylidene)acetoacetamide (3.8g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (1 .7g, yield: 52%). 
       1  H NMR(CDCl 3 ): δ2.7(s,3H), 2.92(s,3H), 8.1˜8.3(m,2H), 15.57(s,1H). 
     EXAMPLE 24 
     3-Acetyl-6-hexyl-4-methylthio-2-quinolinone (37) 
     N-4-Hexylphenyl)-α-(bismethylthioylidene)acetoacetamide (3.7 g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (2.5g, yield: 82%). 
       1  H NMR(CDCl 3 ): δ0.78˜0.97(m,3H), 1.16˜1.8(m,10H), 2.67(s,3H), 2.83(s,3H), 7.57˜8.07(m,3H). 
     EXAMPLE 25 
     3-Acetyl-6,7,8-trifluoro-4-methylthio-2-quinolinone (38) 
     N-(2,3,4-Trifluorophenyl)-α-(bismethylthi oylidene)acetoacetamide (3.4g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (1.8g, yield: 67%). 
       1  H NMR(CDCl 3 ): δ2.73(s,3H), 2.97(s,3H), 7.6˜7.93(m,1H), 15.73(s,1H). 
     EXAMPLE 26 
     3-Acetyl-6-chloro-8-trifluoromethyl-4-(2,4-dichlorobenzylthio)-2-quinolinone (39) 
     N-(4-Chloro- 2-trifluoromethylphenyl)-α-[bis(2,4-dichlorobenzylthio) ylidene]-acetoacetamide (6.0g, 0.01 mol) was used, but the reaction was carried out as the above process of example 1 to obtain the desired product (2.4g, yield: 51%). 
       1  H NMR(CDCl 3 ): δ15.68(s,1H), 8.57(m,1H), 8.17(m,1H), 7.67˜7.03(m,4H), 4.87(s,2H), 2.97(s,3H). 
     EXAMPLE 27 
     3-Acetyl-8-chloro4-methylsulfoxy-2-quinolinone (91) 
     3-Acetyl-8-chloro-4-methylthio-2-quinolinone (26.7g, 0.1 mol)(3) was dissolved in 200 ml of ethyl alcohol, and herein the solution of magnesium monoperoxyphthalate (29.1g, 0.1 mol)dissolved in 150 ml of water was added dropwise at room temperature. 
     After raising the reaction temperature to 50° C., the reacting solution was maintained for 2hr, and then ethyl alcohol was evaporated and 500 ml water was added. 
     The obtained solid w as filtered and recrystallized in 100 ml of ethyl alcohol to afford the desired product (23.2g, yield: 82%). 
       1  H NMR(CDCl 3 ): δ8.3˜7.5(m,3H), 3.1(s,3H), 2.8(s,3H). 
     EXAMPLE 28 
     3-Acetyl-6-methoxy-4-methylsulfoxy-2-quinolinone (92) 
     3-Acetyl-6-methoxy-4-methylthio-2-quinolinone (2.6g, 0.01 mol)(5) was dissolved in 10ml of acetic acid, and the solution was stirred at 80° C., and herein hydrogen peroxide (30% solution 2.83g, 0.025 mol) was added dropwise and stirred for 30min at 80° C. 
     After reacting under the above conditions, the solution was cooled and poured in 500g of ice water, and then the deposited solid was filtered and dried to obtain the desired product (2.3g, yield: 85%). 
       1  H NMR(CDCl 3 ): δ8 7.9˜7.3(m,3H), 3.9(s,3H), 3.0(s,3H), 2.8(s,3H). 
     EXAMPLE 29 
     3-Acetyl-5,8-dichloro-4-methylsulfoxy-2-quinolinone (93) 
     3-Acetyl-5,8-dichloro-4-methylthio-2-quinolinone (3.0g, 0.01 mol)(4) was used, but the reaction was carried out as the above process of example 27 to obtain the desired product (2.4g, yield: 78%). 
       1  H NMR(CDCl 3 ): δ8.0˜7.0(m,2H), 3.1(s,3H), 2.75(s,3H). 
     EXAMPLE 30 
     3-Acetyl-8-fluoro4-methylsulfoxy-2-quinolinone (97) 
     3-Acetyl-8-fluoro-4-methylthio-2-quinolinone (2.5g, 0.01 mol)(8) was used, but the reaction was carried out as the above process of example 27 to obtain the desired product (2.0g, yield: 79%). 
       1  H NMR(CDCl 3 ): δ8.3˜7(m,4H), 3.05(s,3H), 2.82(s,3H). 
     EXAMPLE 31 
     3-Acetyl-6-chloro-8-trifluoromethyl-4-methylsulfoxy-2-quinolinone (98) 
     3-Acetyl-6-chloro-8-trifluoromethyl-4-methylthio-2-quinolinone (3.4g, 0.01 mol)(13) was used, but the reactiota was carried out as the above process of example 27 to obtain the desired product (2.9g, yield: 85%). 
       1  H NMR(CDCl 3 ): δ2.75(s,3H), 3.0(s,3H), 8.6(d,1H), 8.0(d,1H), 11.25(s,1H). 
     EXAMPLE 32 
     3-Acetyl-4-benzylsulfoxy-8-fluoro-2-quinolinone (100) 
     3-Acetyl-4-benzylthio-8-fluoro-2-quinolinone (3.2g, 0.01 mol)(15) was used, but the reaction was carried out as the above process of example 27 to obtain the desired product (2.9g, yield: 87%). 
       1  H NMR(CDCl 3 ): δ2.86(s,3H), 4.37(s,2H), 7.13˜7.47(m,8H), 8.16(s,1H). 
     EXAMPLE 33 
     3-Acetyl-8-trifluoromethyl-4-methylsulfoxy-2-quinolinone (102) 
     3-Acetyl-8-trifluoromethyl-4-methylthio-2-quinolin one (3.0 g, 0.01 mol)(29 ) was used, but the reaction was camed out as the above process of example 27 to obtain the desired product (2.5g, yield: 82%). 
       1  H NMR(CDCl 3 ): 2.87(s,3H), 3.03(s,3H), 7.52˜8.78(m,3H), 11.25(s,1H) 
     EXAMPLE 34 
     3-Acetyl-8-cyano-4-methylsulfoxy-2-quinolinone (104) 
     3-Acetyl-8-cyano-4-methylthio-2-quinolinone (2.6g, 0.01 mol)(29) was used, but the reaction was carded out as the above process of example 27 to obtain the desired product (1.8g, yield: 68%). 
       1  H NMR(CDCl 3 ): δ2.67(s,3H), 7.6˜8.67(m,4H). 
     EXAMPLE 35 
     3-Acetyl-5,8-dichloro- 4-(p-chloro phenyl)thio-2-quinolinone (182) 
     3-Acetyl-5,8-dichloro-4-methylsulfoxy-2-quinolinone (3.2g, 0.01 mol)(93 ) and p-chlorothiophenol(1.73g, 0.012 mol) were stirred at 20° C., heated for 30 min, slowly cooled to 100° C., and dissolved in 15ml of toluene. 
     After cooling to room temperature, the deposited crystal was filtered and dried to obtain the desired product (3.3g, yield: 83%). 
       1  H NMR(CDCl 3 ): 7.2˜8.3(m,6H), 3.00(s,3H). 
     EXAMPLE 36 
     3-Acetyl-5,8-dichloro-4-(p-chlorophenyl)sulfoxy-2-quinolinone (184) 
     3 -Acetyl-5,8-dichloro-4- (p-chlorophenyl)thio-2-quinolinone (1 g, 0.0025 mol) (182) was dissolved in the mixture of 5 ml of acetic acid and hydrogen peroxide (30% solution 0.57g, 0.005 mol), and stirred for 30 min at 100° C. 
     The solution was poured in 50g of ice water, and then the deposited solid was filtered and dried to obtain the desired product (0.8g, yield: 73%). 
       1  H NMR(DMSOd 6  -CDCl 3 ): δ7.2˜8.3(m,6H), 3.05(s,3H). 
     EXAMPLE 37 
     3-Acetyl-6-chloro-8-trifluoromethyl-4-(2-phenylethylamino)-2-quinolinone (223) 
     3-Acetyl-6-chloro-8-trifluoromethyl-4-methylsulfoxy-2-quinolinone (3.5g, 0.01 mol) and 2-phenylethylamine(1.21g, 0.01 mol) were dissolved, refluxed in 50ml of tetrahydrofuran under heating for 4hr. 
     After reacting, the solvent was evaporated under the reduced pressure, and then the obtained solid was dissolved in 10ml of ethylacetate under heating. 
     The solution was recrystallized with adding 30ml of hexane to obtain the desired product (2.57g, yield: 73%). 
       1  H NMR (CDCl 3 ): δ11.78(brs, 1H), 8.47(d, J=2.0, 1H), 7.75(d, J=2.0, 1H), 7.75(brs, 1H), 7.33(s,5H), 3.55(m,2H), 3.08(m,2H), 2.7(s,3H). 
     EXAMPLE 38 
     3-Acetyl-6-chloro-8-trifluoromethyl-4-isopropylamino-2-quinolinone (224) 
     3-Acetyl-6-chloro-8-tfifluoromethyl-4-methylsulfoxy-2-quinolinone (3.5g, 0.01 mol)(13) and isopropylamine (0.6g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.52g, yield: 73%). 
       1  H NMR (CDCl 3 ): δ11.7(s,1H), 8.58(m,1H), 7.87(m,1H), 3.77(m,J =6.5, 1H), 2.93(s,3H), 1.47(d, J=6.5, 6H). 
     EXAMPLE 39 
     3-Acetyl-6-chloro-8-trifiuoromethy- 4-cyclopentylamino-2-quinolinone (227) 
     3-Acetyl-6-chloro-8-trifluoromethyl-4-methylsulfoxy-2-quinolinone (3.5g, 0.01 mol) and cyclopentylamine (0.86g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.5g, yield: 67 % ). 
       1  H NMR (CDCl 3 ): δ11.8(brs, 1H), 8.47(m,1H), 7.83(brs, 1H), 7.77(m,1H), 3.85(brs, 1H), 2.73(s,3H), 2.47˜1.38(m,8H). 
     EXAMPLE 40 
     8-Chloro-3-propionyl-4-isopropylamino-2-quinolinone (229) 
     8-Chloro-4-methylsulfoxy-3-propionyl-2-quinolinone (2.97g, 0.01 mol) and isopmpylamine (0.6g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.93g, yield: 71% ). 
       1  HNMR (CDCl 1 ): δ11.78(br,1H), 8.4˜6.97(m,4H), 3.87(m,J=7.0, 1H), 3.27(q,J=8.0, 2H), 1.65(d, J=7.0, 6H), 1.17(t, J=8.0, 3H). 
     EXAMPLE 41 
     3-Acetyl-8-methyl-4-isopropylamino-2-quinolinone (230) 
     3-Acetyl-8-methyl-4-methylsulfoxy-2-quinolinone (2.63g, 0.01 mol) and isopropylamine (0.6g, 0.01 mol) were used, but the reaction was carded out as the above process of example 37 to obtain the desired product (2.59g, yield: 68%). 
       1  H NMR (DMSO-d6): δ11.5(br. d, 1H), 8.33˜7.23(m,4H), 3.8(m, J=7.0, 1H), 2.77(s,3H), 2.4(s,3H), 1.45(d,J=7.0,6H). 
     EXAMPLE 42 
     3-Acetyl-6-chloro-8-trifluoromethyl-4-(p-fluorophenethyl amino)-2-quinolinone (227) 
     3-Acetyl-6-chloro-8-trifluoromethyl-4-methylsul foxy-2-quinolinone (3.5g, 0.01 mol), p-fluorophenethylamine hydrochloride(1.76g, 0.01 mol) and triethylamine (1.1g, 0.01 mol) were used as the above process of example 37, and the solvent was evaporated under the reduced pressure. 
     The residue was dissolved in 50 ml of ethylacetate, washed with 50 ml of water, dried with magnessium sulfate, and then the solvent was evaporated. 
     The obtained solid was dissolved in 10 ml of ethyl acetate, and crystallized by adding 30 ml of hexane to afford the desired product (2.25g, yield: 53%). 
       1  H NMR (CDCl 3 ): δ2.7(s,3H), 2.97˜3.16(t,J=6.4, 2H), 3.47˜3.77(m,2H), 6.93˜8.47(m,7H), 11.73(s,1H). 
     EXAMPLE 43 
     3-Acetyl-8-fluoro-4-(1-methoxy-2-propylamino)-2-quinolinone (249) 
     3-Acetyl-8-fluoro-4-methylsulfoxy-2-quinolinone (2.67g, 0.01 mol) and 1-methoxy-2-propylamine(0.88g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.53g, yield: 87%). 
       1  H NMR (CDCl 3 ): δ1.5(d,3H), 2.8(s,3H), 3.7˜3.9(m,3H), 3.6(s,3H), 7.2˜8.3(m, 4H). 
     EXAMPLE 44 
     3-Acetyl-6-chloro-8-trifluoromethyl-4-ethylamino-2-quinolinone (251) 
     3-Acetyl-6-chloro-8-trifluoromethyl-4-methylsulfoxy-2-quinolinone (3.5g, 0.01 mol) and ethylamine(70 wt % solution; 0.65g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.52g, yield: 76%). 
       1  H NMR (CDCl 3 ): δ1.37˜1.6(t,J=8, 3H), 2.73(s,3H), 3.23˜3.67(m,2H), 7.77˜8.47(m,3H), 11.57(s,1H). 
     EXAMPLE 45 
     3 -Acetyl- 8- fl uo ro-4- (2 -methyl cyclohexylamino )-2-quinolinone (256) 
     3-Acetyl-8-fiuoro-4-methylsulfoxy-2-quinolinone (2.67g, 0.01 mol) and 2methylcyclohexylamine(1.13g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.1g, yield: 66%). 
       1  H NMR (CDCl 3 ): δ1.0˜1.5(m,12H), 2.6(s,3H), 3.9(m,1H), 7.1˜8.4(m,3H). 
     EXAMPLE 46 
     3-Acetyl-8-trifluoromethyl-4-(a -methylbenzylamino)-2-quinolinone (260) 
     3-Acetyl-8-trifluoromethyl-4-methylsulfoxy-2-quinolinone (3.17 g, 0.01 mol) and α-methylbenzylamine (1.21 g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.43g, yield: 65%). 
       1  H NMR (CDCl 3 ): δ1.63˜1.83 (d,J=7, 3H), 2.8(s,3H), 4.57˜4.77(m,1H), 7.23˜8.6(m,9H), 12.2(s,1H). 
     EXAMPLE 47 
     3-Acetyl-8-chloro-4-(p-chlorobenzylamino)-5-nitro-2-quinolinone (308) 
     3-Acetyl-8-chloro-4-methylsulfoxy-5-nitro-2-quinolinone (3.28g, 0.01 mol ) and p-chlorobenzylamine (1.42g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.32g, yield: 57%). 
       1  H NMR (DMSO-d 6 ): δ8 11.9(m,1H), 8.43(brs, 1H), 7.8(d,J=9.0, 1H), 7.5(s,4H), 7.3(d,J=9.0, 1H), 4.9(d,J=6.0, 2H), 2.7(s,3H). 
     EXAMPLE 48 
     3-Acetyl-6,8-dichloro-4-(2-methylchclohexylamino)-2-quinolinone (311 ) 
     3-Acetyl-6,8-dichloro-4-methylsulfoxy-2-quinolinone (3.18g, 0.01 mol) and 2-methylcyclohexylamine (1.13g, 0.01 mol) were used, but the reaction was carried out as above process of example 37 to obtain the desired product (2.68g, yield: 73%). 
       1  H NMR (CDCl3): δ12.0(m,1H), 8.2(d,J=2.0, 1H), 7.9(brs, 1H), 7.6(d,J=2.0, 1H), 3.0(m,1H), 2.8(s,3H), 1.0˜2.5(m,9H), 1.0˜1.2(m,3H). 
     EXAMPLE 49 
     3-Acetyl-7-t-butyl-4-cyclobutylamino-2-quinolinone (377) 
     3-Acetyl-7-t-butyl-4-methylsulfoxy-2-methylsulfoxy-2-quinolinone (3.05g, 0.01 mol) and cyclobutylamine (0.71g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.6g, yield: 83 % ). 
       1  H NMR (CDCl 3  ): δ11.4(m,1H), 8.3˜8.4(d,1H), 7.2˜7.7(m,2H), 2.9(s,3H), 1.5˜2.9(m,4H), 1.2(s,9H), 0.9˜1.1(m,2H). 
     EXAMPLE 50 
     3-Acetyl-8-ethyl-4-cyclopentylamino-2-quinolinone (400) 
     3-Acetyl-8-ethyl-4-methylsulfoxy-2-quinolinone (2.77g, 0.01 mol) and cyclopentylamine (0.86g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.15g, yield: 72%). 
       1  H NMR (CDCl 3 ): δ11.6(m,1H), 8.1(d,J=6.0, 1H), 7.4˜7.1(m,3H), 3.8(m,1H), 2.8(s,3H), 2.7(m,2H), 2.1˜1.5(m,8H), 1.4(t,J=6.0, 3H). 
     EXAMPLE 51 
     3-Acetyl-6-chloro-8-methyl-4-(p-fluorophenethylamino)-2-quinolinone (420) 
     3-Acetyl-6-chloro-8-methyl-4 -methylsulfoxy -2-quinolinone (2.98 g, 0.01 mol) and p-fluorophenethylamine hydrochloride (1.76g, 0.01 mol) were used, but the reaction was carried out as the above process of example 42 to obtain the desired product (2.9g, yield: 71%). 
       1  H NMR (DMSO-d 6 ): δ11.5(m,1H), 8.3(s,1H), 7.9(s,1H), 7.6˜6.8(m,5H), 3.77(m,2H), 3.0(t,J=7.0, 2H), 2.6(s,3H), 2.4(s,3H). 
     EXAMPLE 52 
     3-Acetyl-5,8-dichloro-4-(N-morpholino)-2-quinolinone (513) 
     3-Acetyl-5,8-dichloro-4-methylsulfoxy-2-quinolinone (3.18g, 0.01 mol) and morpholine (0.87 g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.56g, yield: 75%). 
       1  H NMR (DMSO-d 6 ): δ6.7˜7.3(m,3H), 2.9˜3.3(m, 8H), 2.3(s,3H). 
     EXAMPLE 53 
     3-Acetyl-5,7-dimethyl-4-(β-methylphenethylamino))-2-quinolinone (533) 
     3-Acetyl-5,7-dimethyl-4-methylsulfoxy-2-quinolinone (2.77g, 0.01 mol)and β-methylphenethylamine (1.35g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain hhe desired product (2.96g, yield: 85%). 
       1  H NMR (DMSO-d 6 ): δ11.6(m,1H), 7.2(s,5H), 6.7˜7.1 (d,2H), 3.5(m,2H), 3.2(m,1H), 2.7(s,3H), 2.6(s,3H), 2.2(s, 3H), 1.3(d,3H). 
     EXAMPLE 54 
     3-Acetyl-4-sec-butylamino-8-isopropyl-2-quinolinone (543) 
     3-Acetyl-4-methylsulfoxy-8-isopropyl-2-quinolinone (2.91g, 0.01 mol) and sec-butylamine (0.73g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.7g, yield: 90%). 
       1  H NMR (CDCl 3 ): δ11.6(m,1H), 8.2(d,J=8.0, 1H), 7.7˜7.1(m,3H), 3.5(m,1H), 2.9(m,1H), 2.8(s,3H), 1.7(m,2H), 1.4(m,9H), 1.1(t,J=6.0, 3H). 
     EXAMPLE 55 
     3-Acetyl-4-(β-methylphenethylamino)-8-phenyl-2-quinolinone (565) 
     3-Acetyl-4-methylsulfoxy-8-phenyl-2-quinolinone (3.25g, 0.01 mol) and β-methylphenethylamine (1.35g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (3.29g, yield: 83%). 
       1  H NMR (DMSO-d 6 ): δ11.3(m,1H), 8.3(brs, 1H), 8.3˜8.0(m,1H), 7.8˜6.9(m,12H), 3.3(m,2H), 3.03(m,1H), 2.6(s,3H), 1.23(d,J=7.0, 3H). 
     EXAMPLE 56 
     3-Acetyl-4-allylamino-8-propyl-2-quinolinone (603) 
     3-Acetyl-4-allylamino-8-propyl-2-quinolinone (2.91g, 0.01 mol) and allylamine (0.57g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.31g, yield: 75%). 
       1  H NMR (CDCl 3 ): δ11.6(m,1H), 8.1(d,J=8.0, 1H), 7.7˜7.1(m,3H), 6.0˜5.3(m,3H), 4.1(brs,2H), 2.8(s,3H), 2.6(t,J=7.0, 2H), 1.5(m,2H), 1.0(t,J=6.0, 3H). 
     EXAMPLE 57 
     3-Acetyl-4-allylamino-8-chloro-6-methyl-2-quinolinone (611) 
     3-Acetyl-8-chloro-6-methyl-4 -methylsulfoxy -2-quinolinone (2.97 g, 0.01 mol) and allylamine (0.57g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.38g, yield: 82%). 
       1  H NMR (DMSO-d 6 ): δ11.6(m,1H), 8.2(s,1H), 7.4˜7.7(d,2H), 5.0˜6.1 (m,3H), 3.1 (t,2H), 2.5(s,3H), 2.2(s,3H). 
     EXAMPLE 58 
     3-Acetyl-4-allylamino-5-chloro-6-methyl-2-quinolinone (632) 
     3-Acetyl-5-chloro-6-methyl-4-methylsulfoxy-2-quinolinone (2.69g, 0.01 mol) and allylaminc (0.57g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.23g, yield: 77%). 
       1  NMR (CDCl 3 ): δ11.4(m,1H), 7.1˜7.6(m,3H), 5.1˜6.2(m,3H), 4.0˜4.2(m,2H), 2.6(s,3H), 2.4(s,3H). 
     EXAMPLE 59 
     3-Acetyl-8-chloro-4-(p-chlorophenethylamino-5-methyl-2-quinolinone (656) 
     3-Acetyl-8-chloro-5-methyl-4-methylsulfoxy-2-quinolinone (2.97 g, 0.01 mol) and p-chlorophenethylamine (1.56g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (3.1 lg, yield: 80%). 
       1  H NMR (DMSO-d 6 ): δ11.6(m,1H), 8.7(s,1H), 7.7(s,4H), 7.1˜7.9(m,2H), 3.9(q,2H), 3.2(t,2H), 2.9(s,3H), 2.7(s,3H). 
     EXAMPLE 60 
     3-Acetyl-4-isoamylamino-6-fluoro-8-chloro-2-quinolinone (673) 
     3-Acetyl-8-chloro-6-fluoro-4-methylsulfoxy-2-quinolinone (3.02g, 0.01 mol) and isoamylamine (0.87g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.79g, yield: 86% ). 
       1  H NMR (CDCl 3 ): δ11.6(m,1H), 8.0˜7.8(m,2H), 7.4(dd, J=8.0, 2.0, 1H), 3.4(m,2H), 2.8(s,3H), 1.7(m,3H), 0.9(d,J=6.0, 6H). 
     EXAMPLE 61 
     3-Acetyl-4-isobutylamino-5-trifluoromethyl-8-methoxy-2-quinolinone (682) 
     3-Acetyl-5- trifluoromehyl-8-methoxy-4-methylsulfoxy-2-quinolinone (3.4 7g, 0.01 mol) and isobutylamine (0.73g, 0.01 mol) were used, but the reaction was carried out as the above process of example 37 to obtain the desired product (2.46g, yield: 69%). 
       1  H NMR (DMSO-d 6 ): δ11.1(m,1H), 8.5(brs,1H), 7.2˜7.7(m,2H), 4.2(s,3H), 3.0˜3.6(m,2H), 2.6(s,3H), 1.8˜2.3(m,1H), 1.1 (d,J=6.0, 6H). 
     The fungicidal activities of 2-quinolinone derivatives(I) according to the present invention prepared by the above examples were tested by following Tests; wherein all the test chemicals were readily dispersed in a standard formulation of acetone in water and surfactant. Five ml of acetone containing 12.5 mg of the chemical was diluted in 45 ml of Tween 20 solution (250 ppm). Fifty ml of this chemical solution was sprayed to plants on the ramtable at the same time. All replicates of plants tested for fungicidal activity against 6 plant diseases were two pots, respectively. 
     TEST 1 
     Fungicidal Test for Rice Blast (RCB ) 
     Evaluation of activity against blast was done with rice plants in the 2 leaf stage, grown in 5 cm pots with a foliage spray. Fifty ml test material was sprayed on the foliage. After the spray deposit had dried, the plants were inoculated with a suspension of conidia in water (1×10 6  spores/ml) and placed in a dew chamber at 25° C. for 24 hrs. For inoculum preparation, rice blast fungus was incubated on rice polish agar medium at 26° C. for 2 weeks, and then scratched airial mycelia with rubber and irradiated with near UV light for 2 days. The plants were then held in lighted gowth chamber (26°±2° C., 85%) for an additional 5 days, and rated on the disease severity. 
     TEST 2 
     Fungicidal Test for Rice Sheath Blast (RSB) 
     Rice plants in the 3 leaf stage were sprayed with 5 ml of chemical solution on the turntable. One day after drying, treated plants were inoculated by injecting inoculum, incubated in wileat bran medium at 25° C. for 7 days, macerated into the mixer at the base of the rice plants. Those were moved to a lighted dew chamber at 28° C.and then held for 5 days. The disease severity of each pot was examined and compared to the standard rating diagram. 
     TEST 3 
     Fungicidal Test for Cucumber Gray Mold (CGM) 
     Cucumber plants grown in the fast leaf stage were sprayed with 50 ml of chemical solution while those were rotated on the mintable. After the spray deposit had dried for one day, the treated foliage of cucumber was inoculated with conidia (1×10 6  spores/ml) of B. cinerea incubated on potato dextrose agar medium at 25° C. for 15 days by leaf spray all tour sides of plants until just before runoff and then placed in 20° C. dew chamber for 4˜5 days. The disease rating was made by examining the applied plants and comparing the percent disease on a leaf to the standard rating diagram. 
     TEST 4 
     Fungicidal Test for Tomato Late Blight (TLB) 
     Tests were made onto tomato plants grown in 5 cm polyvinyl pots for 14 days by leaf spray. The foliage is sprayed to run off with a test chemical while the plant rotated on a turntable. After the spray deposit dried for one day, the treated plants were inoculated by spraying then with a suspension of zoosporangia (1×10 5  zoosporangia/ml) incubated on V-8 juice agar medium at 20° C. for 2 weeks and then placed in a dew chamber at 18° C. for 48 hrs. Four days after inoculation, disease ratings were made on a investigation of the disease severity. 
     TEST 5 
     Fungicidal Test for Wheat Leaf Rust (WLR) 
     Tests were made on wheats (cultivar; Chokwang) grown in polyvinyl pots (diameter; 5 cm) for 7 days by foliage spray. The first leaf was sprayed while plaints were rotating on a turntable with 5 ml of a chemical solution. After the spray deposit dried, plants were dusted with a uredospores colonied on the second leaf of wheat and placed in a moist chamber at 20° C. for 24 hours. One day after inoculation, plant were moved to the plant growth chamber (20° C., 70% RH) for inducing the disease. The fungicidal effect of the applied chemicals was investigated on the disease severity of wheats after 10 days. 
     TEST 6 
     Fungicidal Test for Barley Powdery Mildew (BPM) 
     The barley powdery mildew is an obligately parasitic fungus that must be transferred directly from infected plants to healthy plants in a relatively dry environment. The host plants (cultivar; Allbori) sowed in polyvinyl pot(diameter; 5 cm) were grown in a greenhouse for 7 days. Healthy young barley with fully expanded primary leaf was spray with a suspension of a test material. One day after drying, the applied plants were dusted with conidia of Erysiphe graminis formed on the primary leaf of barley. The inoculated plants were placed in a plant growth chamber at 22°˜24° C. and then induced the powdery mildew. The disease severity was rated after 7 day inoculation. 
     Fungicidal activity of test chemical against the above 6 plant diseases was indicated with control value calculated bv below formula to list the result as below Table 4. ##EQU1## 
     
                       TABLE 4______________________________________Fungicidal effects for 2-quinolinoneComp. No.    RCB     RSB     CGM   TLB   WLR   BPM______________________________________ 13      100     80      --    --    100   58 18      97      --      --    --    --    -- 19      84      65      --    97    --    -- 33      96      --      --    --    100   100 34      89      --      --    --    100   84 35      100     100     --    --    --    -- 38      96      68      --    --    100   -- 39      14      45      99    94    29    28 49      95      74      42    78    99    49 55      0       32      92    0     0     51 75      100     100     0     0     99    75106      99      95      57    100   53    10107      94      20      93    99    60    9108      97      67      95    100   53    9111      99      95      95    97    53    10112      99      95      95    97    53    16118      0       30      90    56    0     0120      91      60      95    92    53    0129      0       37      98    38    0     0131      0       16      99    47    53    23137      96      53      94    94    27    0152      99      95      89    60    33    58159      93      90      66    0     91    69165      99      90      83    31    67    0176      99      32      38    73    0     0181      99      63      31    57    75    95183      94      74      0     50    75    18189      94      100     0     0     100   100190      86      90      91    62    45    0191      100     85      42    30    10    33192      100     90      100   18    43    95193      100     95      40    70    100   70194      99      99      81    20    100   55195      100     99      100   0     99    56196      100     86      45    100   42    0197      99      92      0     7     100   83199      99      52      73    61    8     53200      96      52      21    72    56    4204      72      81      0     0     100   100205      100     21      76    98    81    54206      100     91      61    0     100   71211      100     75      21    92    38    8215      84      13      19    0     67    97219      0       20      95    6     53    0222      91      26      69    24    27    0224      100     100     --    --    67    89226      100     --      --    48    --    --228      99      --      --    91    --    --231      100     --      --    --    --    97235      87      11      --    89    --    --236      100     100     35    89    --    --237      --      69      --    93    93    --238      --      100     --    47    98    --239      --      --      --    89    --    --242      100     100     100   --    93    76247      97      --      --    96    --    --251      100     100     --    --    96    --253      --      --      94    --    --    --257      --      --      77    95    --    --259      99      --      --    --    --    --267      71      --      95    35    14    42268      0       0       92    19    0     53272      100     --      66    100   --    --279      99      35      68    87    53    2282      7       0       98    97    0     35308      0       53      15    98    --    --310      0       13      90    37    27    31313      98      53      58    95    60    11336      0       0       100   21    0     13368      18      0       93    0     0     2404      0       0       59    0     99    100407      57      0       38    95    67    29435      93      71      48    91    93    0475      0       10      95    48    67    43476      0       95      67    11    0     61506      0       35      94    65    0     0540      0       20      94    55    0     0542      0       30      94    84    0     0545      0       95      42    82    53    1550      0       58      97    63    0     0608      7       75      82    93    9     0609      0       15      92    21    0     0708      93      28      68    46    0     0709      14      28      92    3     0     0711      0       50      94    13    0     17713      7       5       95    77    0     39715      0       0       100   28    27    4718      96      60      13    78    27    5720      93      30      38    81    53    20721      99      95      59    83    80    5736      100     100     60    71    53    19737      98      80      0     76    82    14745      0       5       92    59    0     16746      0       30      94    71    0     0759      0       10      96    76    0     46761      99      95      0     60    53    95765      0       11      95    36    0     0791      93      61      40    46    0     17792      98      11      81    94    27    29793      91      15      100   47    53    45797      99      60      100   96    53    4798      97      20      13    35    27    32801      99      70      0     65    75    31802      98      70      72    79    68    42803      100     95      99    50    67    24804      99      68      100   29    53    58805      100     95      80    57    60    61806      100     79      56    36    27    14807      99      95      69    57    53    0808      99      95      50    43    53    10809      99      58      71    53    60    2810      99      21      81    73    53    24813      99      37      56    24    33    14830      0       0       93    23    0     20831      0       0       100   46    0     15837      96      60      72    81    36    0839      0       35      96    87    45    15841      57      90      91    86    77    9846      0       0       98    77    0     0853      91      85      78    15    0     98862      99      5       77    0     27    36869      0       100     24    0     96    95870      100     83      3     56    87    0871      100     63      12    73    92    33876      97      33      21    53    81    62877      100     8       15    62    63    53878      100     96      24    0     82    18905      26      0       0     98    96    23908      0       0       0     95    64    5915      100     82      28    85    81    23916      100     82      36    81    76    15928      23      75      67    25    99    61929      90      90      63    0     100   92932      86      95      20    15    96    91933      100     75      40    0     33    70936      100     35      7     25    91    46937      100     15      64    32    27    39939      100     35      14    96    27    81944      50      85      0     0     96    99946      14      90      0     0     100   99947      21      0       24    0     100   97949      94      60      23    0     53    97______________________________________ 
    
     As the result of the above Table 4, the com pounds according to the present invention have a high protective effect against CGM and TLB, and also RCB. 
     The insecticidal activity of the compounds of the formula(I) according to the present invention was tested as following Tests 7˜10. 
     The Primary Screening(PRI) is designed to detect initial pest control activity of experimental compounds. The types of activity assayed are acute toxicity, and growth disruption. The bioassay are designed to detect contact and ingestion activity. 
     The stage tested are as follows: adult brown planthopper(BPH), green peach aphid(GPA), and two-spotted spider mite (TSSM), and 3rd instar diamondback moth(DBM). 
     All experimental compounds are formulated in a 10: 90 (acetone: water), Triton X-100 100ppm solution at a single, unreplicated rate of 500 ppm. Formulated compounds are applied to the test species with the individual application methods respectively. 
     TEST 7 
     Insecticidal Test for Brown Plant Hopper (BPH) 
     Root parts of six rice seddlings (cultivar: Dongjin; 5-6 cm in length; 5-10 day old) are rolled with cotton wool pads and rice seedlings are put into the glass test robes(φ3×15 cm) containing 2 ml water. Three to five day-old adult BPH (20 individuals) are collected from rearing cages by an aspirator, and placed into test robes. 
     Test chemicals are dissolved in 5 ml acetone(100%), and formulated to the proper concentration in Triton X- 100 (100ppm), then sprayed onto the BPH directly. The test tubes are covered with nylon cloth and held in an incubator at 25° C. Insect mortalities are recorded at 24 and 48 hours after treatment. 
     TEST 8 
     lnsecticidal Test for Green Peach Aphid (GPA) 
     Excised tobacco leaf disks (5.5 cm in diameter) are dipped into the prepared test chemical solutions (30 sec) and taken out. After drying (30 min), leaf disks are placed in the petridishes (φ5.5×2 cm) and apterous female adult GPAs (20 individuals) are enclosed. All petridishes are covered and held in an incubator at 25° C. Insect mortalities are recorded at 24 and 48 hours after treatment. 
     TEST 9 
     Insecticidal Test for Two-Spotted Spider Mite (TSSM) 
     Excised kidney bean leaf disks (2.5 cm in diameter) are placed on water saturated cotton wool pads fitted into petridishes (φ5.5×2 cm). Female adult TSSMs (30 individuals) are placed on leaf disks, and prepared test chemicals are sprayed. The petridishes are covered and held in an incubator at 25° C. Mite mortalities are recorded at 24 and 48 hours after teatment. 
     TEST 10 
     Insecticidal Test for Diamond-Back Moth (DBM) 
     Test chemicals axe dissolved in 5ml acetone (100%), then formulated to the proper concentration in Triton X- 100 (100 ppm). Excised cabbage leaf disks(5 cm in diameter) are dipped into the solution (30 sec) and taken out. After drying (30 min), leaf disks are placed in the petridishes (φ5×1 cm) and 3rd instar DBM larvae (10 individuals) are enclosed. All petridshes are covered and held in an incubator at 25° C. Insect mortalities are recorded at 24 and 48 hours after treatment. 
     The mortality (%) of test chemical against the above plant diseases was calculated by the below fomula to list the result as the following Table 5. ##EQU2## 
     
                       TABLE 5______________________________________Insecticidal effects for 2-quinolinone (I)Comp. No.   BPH    GPA       DBM   TSSM______________________________________ 13         --     --        --    100 28         --     --        90    -- 29         20     0         90    100 30         10     0         20    100 33         0      25        40    100 34         5      75        60    100 38         0      30        80    100224         10     0         100    63241         0      0         100    0242         0      0         80    100245         0      0         90    100307         0      10        100    7404         0      0         100   100460         0      0         100    0______________________________________ 
    
     As the result of the above Table 5, the compounds of the formula(I) according to the present invention have selectively good activity against diamond-back moth and two-spotted spider mite.