Azo dyes derived from 5-membered heterocyclic amines and aromatic amine couplers containing sulfo groups, or salts thereof

This invention concerns mono azo dyes derived from diazotized 5-membered heterocyclic amines and certain aniline, 1,2,3,4-tetrahydroquinoline, and benzomorpholine couplers containing sulfoalkyl groups. These dyes are useful for dyeing synthetic fibers, cellulose acetate and wool, and particularly impart fast violet to blue shades on polyamide fibers. The dyes, in general, exhibit improved properties such as fastness to light, sublimation, ozone, oxides of nitrogen, perspiration, crock, and wash, and exhibit excellent build, pH stability, bloom resistance, depth of shade, leveling, migration, and the like.
The dyes of this invention have the general formula:
D--N.dbd.N--Coupler
wherein D is a thiadiazol, isothiazol, pyrazol or thiophene type radical, and the Coupler is an aniline, tetrahydroquinoline, or benzomorpholine derivative wherein a --Z--SO.sub.3 M group is attached to the nitrogen thereof, the coupler ring may contain a substituent such as lower alkyl, lower alkoxy, halogen, acylamido, alkylthio or aryloxy, the remaining hydrogen of the aniline coupler may be replaced by a substituent such as lower alkyl, substituted lower alkyl, lower alkenyl, aryl, or cycloalkyl, M is Na.sup.+, K.sup.+, NH.sub.4.sup.+ or H.sup.+, and Z is a linking group such as ethylene.
More specifically, the Coupler is of the formulae ##STR1## wherein; R.sub.1 is selected from hydrogen, lower alkyl, halogen, lower alkoxy, aryloxy, and --NHCO--R.sub.5 or --NHSO.sub.2 --R.sub.5 wherein R.sub.5 is selected from lower alkyl which may be substituted with hydroxy, lower alkoxy, cyano, aryloxy, aryl, halogen, cycloalkyl, lower alkyl carbonyloxy, or carbamoyl; hydrogen; aryl; alkoxy; alkylamino; and 2-furyl; R.sub.2 is selected from hydrogen, aryl, cycloalkyl, and lower alkyl which may be substituted with alkoxy, alkoxyalkoxy, hydrogen, aryloxy, aryl, cycloalkyl, lower alkylcycloalkyl, furyl, acylamido, aryloxy, carbamoyl, lower alkoxy carbamoyl, lower alkyl substituted carbamoyl, cyano, alkanoyloxy, halogen, alkoxycarbonyl, succinimido, glutarimido, phthalimido, 2-pyrrolidino, sulfamoyl, lower alkyl substituted sulfamoyl, lower alkylsulfonamido, NHSO.sub.2 -aryl, NHCOO-alkyl, NHCONH-alkyl, formamido, alkylsulfonyl, arylsulfonyl, alkylthio, arylthio or SO.sub.3 M; R.sub.2 may in conjunction with R.sub.1 form a 1,2,3,4-tetrahydroquinoline or benzomorpholine derivative; n is 0, 1 or 2; M is Na.sup.+, K.sup.+, NH.sub.4.sup.+, or H.sup.+ ; R.sub.3 and R.sub.4 are each selected from hydrogen or lower alkyl; Z is selected from straight or branched chain lower alkylene, lower alkylene substituted with aryl, aryloxy, alkoxy, halogen, aryloxy or SO.sub.3 M, -CH.sub.2 (CH.sub.2).sub.m -X-CH.sub.2 (CH.sub.2).sub.p, where m is is 1, 2, or 3, p is 0, 1, 2 or 3, and X is O, S, SO.sub.2, ##STR2## and the various aryl groups may be substituted with lower alkyl, lower alkoxy, or halogen. The term "lower" as used through this application means 1-6 carbons.
The heterocycle D is of the formulae ##STR3## ring A may bear a substituent selected from lower alkyl, substituted lower alkyl, lower alkoxy, halogen, lower alkylsulfonyl, SO.sub.2 O aryl, SO.sub.2 NH.sub.2, SO.sub.2 NH--lower alkyl, SO.sub.2 N--(dilower alkyl), arylsulfonyl, substituted SO.sub.2 NH--lower alkyl, acylamido, aryl, arylthio, alkenylthio, cyclohexylthio, thiocyano, cyclohexylsulfonyl, lower alkylthio, substituted lower alkylthio and cyclohexyl;
ring B may bear a substituent selected from lower alkyl, substituted lower alkyl, aryl, lower alkylthio, cyclohexylthio, substituted lower alkylthio and lower alkylsulfonyl;
ring C may bear one or two substituents selected from alkyl, substituted lower alkyl, halogen, cyano, carbamoyl, CONH--lower alkyl, substituted CONH--lower alkyl, lower alkoxycarbonyl, lower alkylthio, substituted lower alkylthio, alkenylthio, arylthio, cyclohexylthio, S-heterocycle, aryloxy, and lower alkoxy;
ring D may bear one or two substituents selected from lower alkyl, substituted lower alkyl, lower alkoxycarbonyl, lower alkylthio, aryl, cyano, carbamoyl, lower alkyl carbamoyl, lower alkylcarbonyl, substituted lower alkyl carbamoyl, and lower alkyl sulfonyl; and
ring E may be substituted with one to three substituents selected from lower alkyl, substituted lower alkyl, cyano, lower alkoxycarbonyl, acyl, aroyl, lower alkylsulfonyl, arylsulfonyl, carbamoyl, lower alkyl carbamoyl, substituted lower alkyl carbamoyl, aryl, halogen, sulfamoyl, lower alkyl carbamoyl, substituted lower alkyl, sulfamoyl and formyl;
and wherein the various alkyl groups may bear one to three substituents selected from hydroxy, lower alkoxy, aryl, aryloxy, cyclohexyl, lower alkylcyclohexyl, acyloxy, lower alkoxy carbonyl, acylamido, lower alkylsulfonamido, succinimido, glutarimido, phthalimido, 2-pyrrolidino, cyano, carbamoyl, lower alkoxy-alkoxy, lower alkylthio, halogen, arylthio, lower alkylsulfonyl and arylsulfonyl;
and wherein the various aryl groups may be substituted with one to three substituents selected from lower alkyl, lower alkoxy, halogen, lower alkoxy carbonyl, lower alkyl sulfonyl, and lower alkylthio.
The following couplers are particularly valuable in the practice of this invention. ##STR4##
The intermedite couplers containing a sulfoethyl group may be prepared in the best purity by reacting aromatic amines such as anilines, tetrahydroquinolines and benzomorpholines with vinylsulfonyl fluoride, followed by basic hydrolysis. Typical is the reaction ##STR5##
Other general methods useful for preparing these couplers containing sulfo groups are given by R. B. Wagner and H. D. Zook, "Synthetic Organic ChemistryS", John Wiley & Sons, Inc., New York, 1953, pp. 812-819. Exemplary are the methods (I) oxidation of mercaptans; (II) alkylation of alkali sulfite; and (III) addition of bisulfites to unsaturated compounds, as follows: ##STR6##
The following coupler intermediates, bearing one or more hydrogens, are typical of those appropriate for reacting with sodium sulfite according to above method II. ##STR7##
The halogen containing couplers are in general prepared by reacting the corresponding known hydroxy compounds with POCl.sub.3, SOCl.sub.2, POBr.sub.3, PBr.sub.3, and the like by methods well known in the art. The tetrahydroquinolines and benzomorpholines are similarly prepared.
The following coupler intermediates are typical of those containing vinyl groups capable of being reacted with sodium bisulfide method III as disclosed, for example, in U.S. Pat. Nos. 3,369,013; 3,415,810; and 3,472,833. ##STR8##
Intermediates containing the acrylamide and vinylsulfonamido groups can be prepared by reacting the corresponding amino compound with acryloyl chloride and vinylsulfonyl fluoride, respectively by methods well known in the art.
Preparation of N-(2-Fluorosulfonylethyl)-N-ethyl-m-toluidine
N-Ethyl-m-toluidine (66.5 g) (0.05 m) is dissolved in isopropyl alcohol (75 ml) and vinylsulfonyl fluoride (55 g 0.5) is added dropwise over 1.25 hr. The reaction exotherms to 38.degree. C. and the reaction mixture is stirred for 1 hr. at ambient temperature and drowned into 500 ml of ice and water. The product is collected by filtration, washed with water, and dried in air. The product melts at 32.degree.-34.degree. C.
Preparation of N-(2-Potassiousulfoethyl)-N-ethyl-m-toluidine
N-(2-Fluorosulfonylethyl)-N-ethyl-m-toluidine (24.5 g., 0.1 m) is stirred in water (200 ml) and potassium hydroxide (10 g) for 1-3 hours at room temperature or until thin-layer chromatography shows the reaction to be complete. The product is not isolated but is used as an aqueous solution in the coupling reaction.
Preparation of N-(2-Fluorosulfonylethyl)-N-ethylaniline
N-Ethylaniline (48.4 g 0.4 m), triethylamine (40.4 g 0.4 m) and benzene (100 ml) are stirred together at room temperature and 2-chloroethanesulfonyl fluoride (58.6 g, 0.4 m) is added dropwise. The reaction mixture is heated at reflux for 1.5 hr. after the addition is completed. The reaction mixture is cooled and filtered to remove any insoluble salts, and the benzene is removed by distillation. The crude product is drowned into hexane (150 ml) and purified by filtration and washing with hexane. The product melts at 48.degree.-50.degree. C.
Preparation of N-(2-Potassiosulfoethyl)-N-ethylaniline
N-(2-Fluorosulfonylethyl)-N-ethylaniline (22.8 g, 0.1 n) is stirred in water (200 ml) and potassium hydroxide (10 g) for 1-3 hrs. or until thin-layer chromatography shows reaction to be complete. The product is not isolated but is used as an aqueous solution in the coupling reaction.
Preparation of N-(2-Fluorosulfonylethyl)-2-methyl-5-acetamidonaniline
2-Methyl-5-acetamido aniline (49.2 g, 0.3 m), triethyl amine (32.7 g 0.3 m) and p-dioxane (350 ml) are stirred together at room temperature. 2-Chloroethane sulfonylfluoride (43.0 g, 0.3 m) is added dropwise allowing temperature to rise to 45.degree. C. The reaction mixture is then heated at reflux for 3 hrs. When thin-layer chromatography shows reaction to be complete, the reaction is allowed to cool and then drowned into water (2000 ml). The product is collected by filtration, washed with water and melts at 154.degree.-155.degree. C.
Preparation of N-(2-Potassiosulfoethyl)-2-methyl-5-acetamido aniline
N-(2-Fluorosulfonylethyl-2-methyl-5-acetamidoaniline (13.7 g, 0.05 m) is stirred with water (100 ml.) and potassium hydroxide (5.0 g) at room temperature for 2 hrs. when thin-layer chromatography shows reaction to be complete. The aqueous solution is used in the coupling reaction without further isolation.
Preparation of N-(2-Fluorosulfonylethyl)-2-methoxy-5-methylaniline
2-Methoxy-5-methylaniline (34.3 g 0.25 m) is dissolved in N,N-dimethylformamide (50 ml). Vinylsulfonyl fluoride (28.0 g, 0.26 m) is added dropwise at 20.degree.-30.degree. C. After the addition is complete the reaction mixture is allowed to stir at ambient temperature for 1 hr. The reaction is drowned into water (400 ml)., the product collected by filtration, washed with water and air dried. The product melts at 56.degree.-58.degree. C. The corresponding N-(2-potassiosulfoethyl)-2-methoxy-5-methylaniline is prepared therefrom by the above technique using KOH.
Preparation of N-(2-Fluorosulfonylethyl)-2,2,4,7-tetramethyl 1,2,3,4-tetrahydroquinoline
2,2,4,7-Tetramethyl-1,2,3,4-tetrahydroquinoline (94.5 g, 0.5 m) is dissolved in acetic acid (200 ml). The reaction is heated to 50.degree. C. and vinylsulfonylfluoride (44.0 g, 0.5 m) added over 30 min. at 48.degree.-50.degree. C. The reaction is then stirred and heated for 2.5 hr. at 50.degree.-55.degree. C. Thin-layer chromatography shows the reaction to be complete. The reaction mixture is drowned into water (1200 ml), the product collected by filtration, washed with water and air dried. The product melts at 67.degree.-69.degree. C.
N-(2-fluorosulfonylethyl)-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline and N-(2-fluorosulfonylethyl 2,7-dimethyl-1,2,3,4-tetrahydroquinoline is prepared in same manner.
Preparation of N-(2-Sodiosulfoethyl)-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline
N-(2-fluorosulfonylethyl)-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline (12.0 g, 0.04 m) is stirred with water (100 ml) and sodium hydroxide (5.0 g(, warmed to 50.degree. C. for 30 min., allowed to come to room temperature and stirred for 1.5 hr. Thin layer chromatography shows the reaction to be complete. The aqueous solution is not isolated but is used in the coupling reaction.
The same process is used to prepare N-(2-potassiosulfoethyl)-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline and N-(2-potassiosulfoethyl)-2,7-dimethyl-1,2,3,4-tetrahydroquinoline using KOH as the base.
Preparation of N-(2-Flourosulfonylethyl)-3,6-dimethyl-2,3-dihydro-1,4-benzoxazine
3,6-Dimethyl-2,3-dihydro-1,4-benzoxazine (16.3 g, 0.1 m) is dissolved in acetic acid (40 ml) at ambient temperature and vinylsulfonylfluoride (11 g., 0.1 m) is added dropwise at 25.degree.-35.degree. C. After stirring for 1.5 hr., the reaction is complete. The reaction is drowned into water (400 ml). The dark oil which separates is extracted with hexane (1200 ml) and the hexane solution dried over sodium sulfate. The sodium sulfate is removed and the hexane distilled off to yield 23.3 g. of oily product. The N-2(Potassiosulfoethyl)-3,6-dimethyl-2,3-dihydro-1,4-benzoxazine is prepared as above using KOH.
Preparation of N-(2-Fluorosulfonylethyl)-N-ethyl-m-acetamidoaniline
N-ethyl-m-acetamidoaniline (178.0 g, 1.0 m is dissolved in isopropyl alcohol (450 ml) and vinylsulfonylfluoride (110 g, 1.0 m) is added dropwise allowing temperature to rise to 40.degree. C. The reaction is stirred for 2.5 hrs., the product collected by filtration, washed with cold ethanol and air dried.
Preparation of N-(2-Sodiosulfoethyl)-sulfonylethyl-N-ethyl-m-toluidine
N-(2-vinylsulfonylethyl-N-ethyl-m-toluidine (25.3 g, 0.1 m) in water solution (100 ml) is stirred with sodium bisulfite (11.0 g, 0.1 m). The reaction is heated to reflux and held for 15 min. The clear solution is drowned into ethanol (200 ml) and allowed to cool. The white solid is collected by filtration, air dried and melts at 237.degree.-240.degree. C.
Vinylsulfonyl fluoride may be prepared according to U.S. Pat. Nos. 2,653,973 and 2,884,452 and L. Z. Soboronskii, et. al., J. Gen. Chem. U.S.S.R., 28, 1913 (1958). The amine diazo precursors can be prepared from readily available intermediates by well known techniques.
This invention will be further illustrated by the following examples although it will be understood that these examples are included merely for purposes of illustration and are not intended to limit the scope of the invention.

EXAMPLES 1-10
Diazotization and Coupling of 2-Amino-5-ethylthio-1,3,4-thiadiazole
Sodium nitrite (3.6 g.) is added portionwise to 25 ml of concentrated H.sub.2 SO.sub.4. The solution is cooled and 100 ml of 1:5 acid (1 part propionic: 1 part acetic) is added below 15.degree. C. The mixture is cooled and 8.05 g. (0.05 m) of 2-amino-5-ethylthio-1,3,4-thiadiazole is added below 10.degree. C. After stirring at 0.degree.-5.degree. C. for 2 hrs., a 0.005 m aliquot of the diazonium salts is added to 0.005 m of the following couplers in water or dilute sulfuric acid, keeping the temperature below 5.degree. C.
N-Ethyl-N-2-sulfoethyl-m-toluidine, K salt (Example 1)
N-Ethyl-N-sulfoethyl-2-methoxy-5-methylaniline, K salt (Example 2).
5-Acetamido-2-methyl-N-sulfoethyl aniline, K salt (Example 3).
N-(2-Sulfoethyl)-1,2,3,4-tetrahydro-2,2,4,7-tetramethyl quinoline, K salt (Example 4)
N-(2-Sulfoethyl)-1,2,3,4-tetrahydro-2,2,4-trimethyl quinoline, K salt (Example 5)
2,7-Dimethyl-N-(2-sulfoethyl)-1,2,3,4-tetrahydroquinoline, K salt (Example 6)
8-Methoxy-5-methyl-N-(2-sulfoethyl)-1,2,3,4-tetrahydro quinoline, K salt (Example 7)
2,7-Dimethyl-N-(2,3-disulfopropyl)-1,2,3,4-tetrahydro quinoline, K salt (Example 8)
2,3-Dihydro-3,6-dimethyl-N-(2-sulfoethyl)-1,4-benzoxazine, K salt (Example 9)
2,3-Dihydro-3-methyl-7-methoxy-N-(2-sulfoethyl)-1,4-benzoxazine, K salt (Example 10)
The mineral acid is neutralized with potassium acetate and the coupling mixture allowed to stand for 1 hr. Water is added to make a total volume of 200-300 ml. and the dyes are collected by filtration, washed with water, and dried in air.
The dyes usually contain about an equal weight of dye and potassium sulfate as they are isolated and are used for dying polyamide fibers red shades without further purification. The dyes in the following tables are prepared in a similar manner. Neutralization using sodium hydroxide and ammonium hydroxide results in the corresponding sodium and ammonium salts, respectively.
TABLE 1__________________________________________________________________________ ##STR9##R (R.sub.1).sub.m R.sub.2 Z M__________________________________________________________________________5-CH.sub.3 2-CH.sub.3 H CH.sub.2 CH.sub.2 K.sup.+5-CH.sub.2 CH.sub.3 2-Cl " " "5-CH.sub.2 CH(CH.sub.3) 2,5-di-Cl " " "5-C.sub.6 H.sub.5 2,5-di-CH.sub.3 " " "5-C.sub.6 H.sub.11 2,5-di-OCH.sub.3 " " "5-C.sub.6 H.sub.4p-Cl 3-OCH.sub.3 C.sub.2 H.sub.5 " "5-C.sub.6 H.sub.4o-CH.sub.3 2-OCH.sub.3, 5-NHCOCH.sub.3 H " "5-C.sub.6 H.sub.4m-OCH.sub.3 2-CH.sub.3, 3-Cl " " "5-SCH.sub.3 2-OCH.sub.3, 5-Cl " " "" 3-NHCOCH.sub.3 C.sub.2 H.sub.5 " "" 3-NHCOC.sub.2 H.sub.5 C.sub.2 H.sub.4 OCH.sub.3 " "" 3-NHCOCH.sub.2 OH CH.sub.2 C.sub.6 H.sub.5 " "" 3-NHCOCH.sub.2 OCH.sub.3 C.sub.6 H.sub.11 " "" 3-NHCOC.sub.6 H.sub.5 CH.sub.2 C.sub.6 H.sub.11 " "" 3-NHCOOC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5 " "" 3-NHCONHC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OH " "5-OC.sub.2 H.sub.5 3-NHCOC.sub.6 H.sub.11 CH.sub.2 CH(CH.sub.3).sub.2 " "5-SC.sub.2 H.sub.5 3-NHCOCH.sub.2 CN CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 " "" 3-NHCOCH.sub.2 OC.sub.6 H.sub.5 CH.sub.2 CH.sub.2 OCOCH.sub.3 " "" 3-NHCOCH.sub.2 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 CONH.sub.2 " "" 3-CH.sub. 3 CH.sub.2 CH.sub.2 NHCOCH.sub.3 " "" " CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3 " "" " CH.sub.2 CH.sub.2 SO.sub.2 NH.sub.2 " "" " CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3 " "5-Cl " CH.sub.2 CH.sub.2 SCH.sub.3 " "5-SO.sub.2 CH.sub.3 " ##STR10## CH.sub.2 CH.sub.2 CH.sub.2 Na.sup.+5-OC.sub.4 H.sub.9n " ##STR11## " "5-SCH.sub.2 CH.sub.2 OH 3-OC.sub.6 H.sub.5 ##STR12## " NH.sub.4.sup.+ 35-SCH.sub.2 CH.sub.2 COOCH.sub.3 3-CH.sub.3 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 Na.sup.+ ##STR13## " ##STR14## CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5) "5-SCH.sub.2 SC.sub.6 H.sub.5 " CH.sub.2 CH.sub.2 COOCH.sub.3 CH.sub.2 CH(C.sub.6 H.sub.5) "5-SO.sub.2 CH.sub.3 " CH.sub.2 CH.sub.2 CN CH.sub.2 CH(CH.sub.3) "5-SO.sub.2 NH.sub.2 " C.sub.2 H.sub.5 CH.sub.2 CH(OH)CH.sub.2 "5-SO.sub.2 NHC.sub.2 H.sub.5 2-CH.sub.3 S H CH.sub.2 CH.sub.2 CH.sub.2 "H.sub.25-SCN 3-CH.sub.3 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2 CH.sub.2 CH(OCOCH.sub.3)CH.sub.2 "5-SO.sub.2 N(CH.sub.3).sub.2 " CH.sub.2 CH(OH)CH.sub.2 Cl CH.sub.2 CH.sub.2 "5-SO.sub.3 C.sub.6 H.sub.5 2-OCH.sub.3, 5-CH.sub.3 C.sub.2 H.sub.5 " "5-SCH.sub.2 CHCH.sub.2 " H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 "5-SCH.sub.2 CH.sub.2 OCH.sub.3 " H " " ##STR15## " " CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 K.sup.+5-SC.sub.6 H.sub.11 3-CH.sub.3 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 "5-SC.sub.6 H.sub.5 " " CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 "5-SO.sub.2 C.sub.6 H.sub.5 " " CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 "H.sub.25-I " " CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2 CH.sub.2 "5-Br " " CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.s ub.2 CH.sub.2 " ##STR16## " " CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4 "5-SCH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3 " " CH.sub.2 CH.sub.2 NHCOCH.sub.2 "5-SCH.sub.2 CH.sub.2 NHCOCH.sub.3 " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "5-SCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5 " " CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 "5-SCH.sub.2 CH.sub.2 C.sub.6 H.sub.5 " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.5)CH.sub.2 "H.sub.25-SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.11)CH.sub.2 CH.sub.2 "5-SO.sub.2 C.sub.6 H.sub.11 " " CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.s ub.2 CH.sub.2 "5-CH.sub. 3 " " CH.sub.2 CH(CH.sub.2 OCH.sub.3) "" " " CH.sub.2 CH(Cl)CH.sub.2 "" " " CH.sub.2 CH.sub.2 NHCONHC.sub.2 H.sub.4 "5-NHCOCH.sub.3 " " CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2 "__________________________________________________________________________
TABLE 2__________________________________________________________________________ ##STR17##R (R.sub.1).sub.m R.sub.3 R.sub.4 Z M__________________________________________________________________________H H CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 K.sup.+" 7-CH.sub.3 " " " "" 7-OCH.sub.3 " " " "5-CH.sub.3 7-Cl " " " "5-CH.sub.2 CH.sub.3 5-CH.sub.3, 8-OCH.sub.3 " " " "5-CH(CH.sub.3).sub.2 5,8-di-OCH.sub.3 " " " "5-CH.sub.2 CH(CH.sub.3).sub.2 5,8-di-CH.sub.3 " " " "5-C.sub.6 H.sub.5 5-Cl, 8-OCH.sub.3 " " " "5-C.sub.6 H.sub.11 8-OCH.sub.3 " " " "5-C.sub.6 H.sub.4o-Cl 8-OC.sub.2 H.sub.5 H H " "5-C.sub.6 H.sub.4n-CH.sub.3 7-CH.sub.3 " " " "5-C.sub.6 H.sub.4p-OCH.sub.3 7-NHCOCH.sub.3 CH.sub.3 CH.sub.3 " Na.sup.+5-OC.sub.2 H.sub.5 7-NHCOH " " " "" 7-NHCOCH.sub.2 OCH.sub.3 " " " "" 7-NHCOCH.sub.2 OC.sub.6 H.sub.5 H CH(CH.sub.3).sub.2 " "" 7-NHCOCH.sub.2 C.sub.6 H.sub.5 " " " "" 7-NHCOCH.sub.2 Cl " " " "" 7-NHCOC.sub.6 H.sub.5 " " " "" 7-NHCOC.sub.6 H.sub.11 CH.sub.3 CH.sub.3 " "5-Cl 7-NHCONHC.sub.2 H.sub.5 " " " "" 7-NHSO.sub.2 CH.sub.3 " " " "" 7-NHCOCH.sub.2 CN " " " "" 7-NHCOCH.sub.2 OH " " " "5-I 7-NHCOOC.sub.2 H.sub.5 " " CH.sub.2 CH.sub.2 CH.sub.2 "5-Br ##STR18## " " " "5-SO.sub.2 CH.sub.3 8-OC.sub.4 H.sub.9n H CH.sub.3 CH.sub.2 CH.sub.2 "5-SO.sub.2 NH.sub.2 7-CH.sub.3 CH.sub.3 H " "5-SO.sub.2 N(CH.sub.3).sub.2 ##STR19## " CH.sub.3 " "5-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 7-OC.sub.2 H.sub.5 " " " "8-SO.sub.2 NHC.sub.3 H.sub.6 OCH.sub.3 7-OC.sub.4 H.sub.9n " " " "5-SO.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 7-CH.sub.3 " H " "5-SC.sub.6 H.sub.5 " " " " "5-SC.sub.6 H.sub.11 " " " CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 "5-SO.sub.2 C.sub.6 H.sub.5 " " " CH.sub.2 CH.sub.2 "5-SO.sub.3 C.sub.6 H.sub.5 " " " " "5-SCH.sub.2 CH.sub.2 OH " " " " "5-SCH.sub.2 CHCH.sub.3 " " " CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 K.sup.+5-SCH.sub.2 COOC.sub.2 H.sub.5 " " " CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 "5-SCH.sub.2 C.sub.6 H.sub.5 " " " CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 "5-SCH.sub.2 C.sub.6 H.sub.11 " " " CH.sub.2 CH(C.sub.6 H.sub.5) "5-SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 " " " CH.sub.2 CH(CH.sub.3) "5-SCN " " " CH.sub.2 CH(OH)CH.sub.2 "5-SCH.sub.2 CH.sub.2 NHCOCH.sub.3 " " " CH.sub.2 CH(Cl)CH.sub.2 " ##STR20## " " " CH.sub.2 CH(CH.sub.2 OCH.sub.2 CH.sub.3) "5-SCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5 " " " CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5) "5-SCH.sub.2 CH.sub.3 " " " CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH .sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 NHCOCH.sub.2 "" " " " CH.sub.2 CH.sub.2 NHCOOCH.sub.2 "H.sub.2" " " " CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4 "5-SCH.sub.3 " " " CH.sub.2 CH.sub.2 NHCONHC.sub.2 ".sub.4" " " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "5-NHCOCH.sub.3 " " " CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH .sub.2 CH.sub.2 "__________________________________________________________________________
TABLE 3__________________________________________________________________________ ##STR21##R (R.sub.1).sub.m R.sub.3 Z M__________________________________________________________________________H 6-CH.sub.3 H CH.sub.2 CH.sub.2 K.sup.+" H H " "" " CH.sub.3 " "5-CH.sub.3 6-CH.sub.3 " " "5-CH(CH.sub.3).sub.2 " " CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 "5-CH.sub.2 CH(CH.sub.3).sub.2 6-OCH.sub.3 " " "5-C.sub.6 H.sub.5 " " CH.sub.2 CH.sub.2 "5-C.sub.6 H.sub.4p-Cl 6-CH.sub.3 " CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 "5-C.sub.6 H.sub.4p-OCH.sub.3 " " CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 "5-C.sub.6 H.sub.4n-CH.sub.3 " " CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 "5-OC.sub.2 H.sub.5 " " CH.sub.2 CH(CH.sub.3) "5-OCH(CH.sub.3).sub.2 " " CH.sub.2 CH(C.sub.6 H.sub.5) "5-C.sub.6 H.sub.11 6-OC.sub.2 H.sub.5 " CH.sub.2 CH.sub.2 "5-SCN 6-NHCOCH.sub.3 " " Na.sup.+5-SCH.sub.3 6-NHCOH " " "5-SCH.sub.2 CH(CH.sub.3).sub.2 6-NHCOCH.sub.2 CH.sub.2 OCH.sub.3 " " "5-SCH.sub.2 CHCH.sub.2 6-NHCOCH.sub.2 Cl " " "5-SC.sub.6 H.sub.11 6-NHCOCH.sub.2 CN " " "5-SC.sub.6 H.sub.5 6-NHCOCH.sub.2 CONH.sub.2 " " "5-SCH.sub.2 C.sub.6 H.sub.5 6-NHCOCH.sub.2 OC.sub.6 H.sub.5 " " "5-SCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5 6-NHCOOC.sub.2 H.sub.5 " " "5-SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 6-NHCONHC.sub.2 H.sub.5 " " "5-SCH.sub.2 CH.sub.2 OH 6-NHCOC.sub.6 H.sub.5 " " "5-SCH.sub.2 CH.sub.2 Cl 6-NHCOC.sub.6 H.sub.11 " " "5-SCH.sub.2 COOC.sub.2 H.sub.5 6-NHSO.sub.2 CH.sub.3 " " "5-SCH.sub.2 CH.sub.2 OCOCH.sub.3 6-NHCOCH.sub.2 CH.sub.2 OCOCH.sub.3 " " "5-SCH.sub.2 C.sub.6 H.sub.11 ##STR22## " " "5-SO.sub.2 CH.sub.3 6-NHCOCH.sub.2 CH.sub.2 CH.sub.2 OH " " "5-SO.sub.2 C.sub.4 H.sub.9n 6-CH.sub.3 " CH.sub.2 CH.sub.2 CH.sub.2 "5-SO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 " " CH.sub.2 CH.sub.2 "5-SO.sub.2 C.sub.6 H.sub.5 " " " "5-SO.sub.2 C.sub.6 H.sub.11 " " " "5-SO.sub.2 CH.sub.2 C.sub.6 H.sub.5 " " " "5-SO.sub.2 CH.sub.2 CH.sub.2 OH " " " " ##STR23## " " " "5-SCH.sub.2 CH.sub.2 NHCOCH.sub.3 " " " " ##STR24## " H CH.sub.2 CH(CH.sub.3) "5-SO.sub.2 NH.sub.2 " CH.sub.3 CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.su b.2 CH.sub.2 K.sup.+5-SO.sub.2 NHC.sub.3 H.sub.6 OCH.sub.3 " " CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2 CH.sub.2 "5-SO.sub.2 NH(CH.sub.3).sub.2 " " CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH.su b.2 CH.sub.2 CH.sub.2 "5-SO.sub. 2 NHC.sub.2 H.sub.5 " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "5-SO.sub.2 NHC.sub.6 H.sub.11 " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.11)CH.sub.2 CH.sub.2 "5-SO.sub.3 C.sub.6 H.sub.5 " " CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 "5-SO.sub.2 NHC.sub.6 H.sub.5 " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3)CH.sub.2 CH.sub.2 "5-NHCOCH.sub.3 " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.11)CH.sub.2 CH.sub.2 "5-SC.sub.2 H.sub.5 " " CH.sub.2 CH(Cl)CH.sub.2 "" " " CH.sub.2 CH(OH)CH.sub.2 "" " " CH.sub.2 CH(CH.sub.2 OCH.sub.3) "" " " CH.sub.2 CH(CH.sub.2 OC.sub.6 ".sub.5)" " " CH.sub.2 CH(OCOCH.sub.3)CH.sub.2 "" " " CH.sub.2 CH.sub.2 NHCOCH.sub.2 "" " " CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4 "" " " CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 NHCONHCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 N(COC.sub.6 H.sub.5)CH.su b.2 CH.sub.2 "__________________________________________________________________________
TABLE 4__________________________________________________________________________ ##STR25##R (R.sub.1).sub.m R.sub.2 Z M__________________________________________________________________________3-CH.sub.3 2-CH.sub.3 H CH.sub.2 CH.sub.2 K.sup.+" 2-Cl " " "" 2,5-di-Cl " " "" 2,5-di-CH.sub.3 " " "" 2,5-di-OCH.sub.3 " " "" 3-OCH.sub.3 C.sub.2 H.sub.5 " "" 2-OCH.sub.3, 5-NHCOCH.sub.3 H " "3-SCH.sub.3 2-CH.sub.3, 3-Cl " " "3-C.sub.6 H.sub.5 2-OCH.sub.3, 5-Cl " " "3-C.sub.6 H.sub.4 p-Cl 3-NHCOCH.sub.3 C.sub.2 H.sub.5 " "3-C.sub.6 H.sub.4o-CN 3-NHCOC.sub.2 H.sub.5 C.sub.2 H.sub.4 OCH.sub.3 " "" 3-NHCOCH.sub.2 OH CH.sub.2 C.sub.6 H.sub.5 " "" 3-NHCOCH.sub.2 OCH.sub.3 C.sub.6 H.sub.11 " "" 3-NHCOC.sub.6 H.sub.5 CH.sub.2 C.sub.6 H.sub.11 " "" 3-NHCOOC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5 " "" 3-NHCONHC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OH " "" 3-NHCOC.sub.6 H.sub.11 CH.sub.2 CH(CH.sub.3).sub.2 " "3-C.sub.6 H.sub.5 3-NHCOCH.sub.2 CN CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 " "" 3-NHCOCH.sub.2 OC.sub.6 H.sub.5 CH.sub.2 CH.sub.2 OCOCH.sub.3 " "" 3-NHCOCH.sub.2 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 CONH.sub.2 " "" 3-CH.sub.3 CH.sub.2 CH.sub.2 NHCOCH.sub. 3 " "" " CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3 " "3-C.sub.6 H.sub.4p-CH.sub.2 " CH.sub.2 CH.sub.2 SO.sub.2 NH.sub.2 " "3-C.sub.6 H.sub.5 " CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3 " "" " CH.sub.2 CH.sub.2 SCH.sub.3 " "" " ##STR26## CH.sub.2 CH.sub.2 CH.sub.2 Na.sup.+" " ##STR27## " "" 3-OC.sub.6 H.sub.5 ##STR28## " NH.sub.4.sup.+" 3-CH.sub.3 C.sub.6 H.sub.5 CH.sub. 2 CH.sub.2 Na.sup.+" " ##STR29## CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5) "3-SO.sub.2 CH.sub.3 " CH.sub.2 CH.sub.2 COOCH.sub.3 CH.sub.2 CH(C.sub.6 H.sub.5) "3-SCH.sub.2 CH.sub.2 COOCH.sub.3 " CH.sub.2 CH.sub.2 CN CH.sub.2 CH(CH.sub.3) "3-SCH.sub.2 C.sub.6 H.sub.5 " C.sub.2 H.sub.5 CH.sub.2 CH(OH)CH.sub.2 "3-SCH.sub.2 CH.sub.2 OCH.sub.3 2-CH.sub.3 S H CH.sub.2 CH.sub.2 CH.sub.2 "H.sub.23-SC.sub.6 H.sub.11 3-CH.sub.3 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2 CH.sub.2 CH(OCOCH.sub.3)CH.sub.2 "3-SC.sub.2 H.sub.5 " CH.sub.2 CH(OH)CH.sub.2 Cl CH.sub.2 CH.sub.2 "" 2-OCH.sub.3, 5-CH.sub.3 C.sub.2 H.sub.5 " "" " H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 "" " H " "" " " CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 K.sup.+3-SCH.sub.2 COOCH.sub.3 3-CH.sub.3 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 "H.sub.2" " " CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2 CH.sub.2 "3-SCH.sub.3 " " CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.s ub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4 "" " " CH.sub.2 CH.sub.2 NHCOCH.sub.2 "" " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "3-SCH.sub.2 CH(CH.sub.3).sub.2 " " CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.5)CH.sub.2 "H.sub.2" " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.11)CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.s ub.2 CH.sub.2 "" " " CH.sub.2 CH(CH.sub.2 OCH.sub.3) "" " " CH.sub.2 CH(Cl)CH.sub.2 "" " " CH.sub.2 CH.sub.2 NHCONHC.sub.2 H.sub.4 "" " " CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2 "__________________________________________________________________________
TABLE 5__________________________________________________________________________ ##STR30##R (R.sub.1).sub.m R.sub.3 R.sub.4 Z M__________________________________________________________________________3-CH.sub.3 H CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 K.sup.+" 7-CH.sub.3 " " " "" 7-OCH.sub.3 " " " "" 7-Cl " " " "" 5-CH.sub.3, 8-OCH.sub.3 " " " "" 5,8-di-OCH.sub.3 " " " "" 5,8-di-CH.sub.3 " " " "" 5-Cl, 8-OCH.sub.3 " " " "" 8-OCH.sub.3 " " " "" 8-OC.sub.2 H.sub.5 H H " "3-SCH.sub.3 7-CH.sub.3 " " " "3-C.sub.6 H.sub.5 7-NHCOCH.sub.3 CH.sub.3 CH.sub.3 " Na.sup.+" 7-NHCOH " " " "" 7-NHCOCH.sub.2 OCH.sub.3 " " " "" 7-NHCOCH.sub.2 OC.sub.6 H.sub.5 H CH(CH.sub.3).sub.2 " "" 7-NHCOCH.sub.2 C.sub.6 H.sub.5 " " " "" 7-NHCOCH.sub.2 Cl " " " "" 7-NHCOC.sub.6 H.sub.5 " " " "" 7-NHCOC.sub.6 H.sub.11 CH.sub.3 CH.sub.3 " "" 7-NHCONHC.sub.2 H.sub.5 " " " "" 7-NHSO.sub.2 CH.sub.3 " " " "" 7-NHCOCH.sub.2 CN " " " "C.sub.6 H.sub.4o-CN 7-NHCOCH.sub.2 OH " " " "" 7-NHCOOC.sub.2 H.sub.5 " " CH.sub.2 CH.sub.2 CH.sub.2 " ##STR31## " " " "" 8-OC.sub.4 H.sub.9n H CH.sub.3 CH.sub.2 CH.sub.2 "3-C.sub.6 H.sub.4p-CH.sub.3 7-CH.sub.3 CH.sub.3 H " "3-C.sub.6 H.sub.4o-Cl ##STR32## " CH.sub.3 " "3-SO.sub.2 CH.sub.3 7-OC.sub.2 H.sub.5 " " " "3-SC.sub.6 H.sub.11 7-OC.sub.4 H.sub.9n " " " "3-SCH.sub.2 CH.sub.2 OCH.sub.3 7-CH.sub.3 " H " "3-SCH.sub.2 CH.sub.2 COOCH.sub.3 " " " " "3-SCH.sub.2 C.sub.6 H.sub.5 " " " CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 "3-CH.sub.2 CH.sub.3 " " " CH.sub.2 CH.sub.2 "3-SCH.sub.2 COOCH.sub.3 " " " " "3-SCH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5 " " " " "3-SCH.sub.2 CH.sub.2 COOCH(CH.sub.3).sub.2 " " " CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 K.sup.+3-SO.sub.2 C.sub.4 H.sub.9n " " " CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 "3-SCH.sub.2 CH.sub.2 CONHC.sub.4 H.sub.9n " " " CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 "3-SCH.sub.3 " " " CH.sub.2 CH(C.sub.6 H.sub.5) "" " " " CH.sub.2 CH(CH.sub.3) "3-SC.sub.2 H.sub.5 " " " CH.sub.2 CH(OH)CH.sub.2 "" " " " CH.sub.2 CH(Cl)CH.sub.2 "" " " " CH.sub.2 CH(CH.sub.2 OCH.sub.2 CH.sub.3) "" " " " CH.sub.2 CH(CH.sub.2 OC.sub.6 ".sub.5)" " " " CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3) CH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 NHCOCH.sub.2 "" " " " CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 COOCH.sub.2 "H.sub.2" " " " CH.sub.2 CH.sub.2 CONHC.sub.2 ".sub.4" " " " CH.sub.2 CH.sub.2 NHCONHC.sub.2 H.sub.4 "" " " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub. 2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3) CH.sub.2 CH.sub.2 "__________________________________________________________________________
TABLE 6__________________________________________________________________________ ##STR33##R (R.sub.1).sub.m R.sub.3 Z M__________________________________________________________________________3-CH.sub.3 6-CH.sub.3 H CH.sub.2 CH.sub.2 K.sup.+" H H " "" " CH.sub.3 " "" 6-CH.sub.3 " " "" " " CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 "" 6-OCH.sub.3 " " "3-SCH.sub.3 " " CH.sub.2 CH.sub.2 "3-CH.sub.2 CH.sub.3 6-CH.sub.3 " CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 "3-SCH.sub.2 CH.sub.2 OCH.sub.3 " " CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 "3-SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 " " CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 "3-SCH.sub.2 CH.sub.2 COOCH.sub.3 " " CH.sub.2 CH(CH.sub.3) "3-SCH.sub.2 COOCH.sub.2 CH.sub.3 " " CH.sub.2 CH(C.sub.6 H.sub.5) "3-SCH.sub.2 C.sub.6 H.sub.5 6-OC.sub.2 H.sub.5 " CH.sub.2 CH.sub.2 "3-SC.sub.6 H.sub.11 6-NHCOCH.sub.3 " " Na.sup.+3-SCH.sub.3 6-NHCOH " " "" 6-NHCOCH.sub.2 CH.sub.2 OCH.sub.3 " " "" 6-NHCOCH.sub.2 Cl " " "" 6-NHCOCH.sub.2 CN " " "" 6-NHCOCH.sub.2 CONH.sub.2 " " "" 6-NHCOCH.sub.2 OC.sub.6 H.sub.5 " " "3-SO.sub.2 CH.sub.3 6-NHCOOC.sub.2 H.sub.5 " " "3-SO.sub.2 C.sub.4 H.sub.9n 6-NHCONHC.sub.2 H.sub.5 " " "3-C.sub.6 H.sub.5 6-NHCOC.sub.6 H.sub.5 " " "3-C.sub.6 H.sub.4o-CN 6-NHCOC.sub.6 H.sub.11 " " "3-C.sub.6 H.sub.4o-Cl 6-NHSO.sub.2 CH.sub.3 " " "3-C.sub.6 H.sub.4p-CH.sub.3 6-NHCOCH.sub.2 CH.sub.2 OCOCH.sub.3 " " "3-C.sub.6 H.sub.4m-CH.sub.3 ##STR34## " " "3-C.sub.6 H.sub.4o-CH.sub.3 6-NHCOCH.sub.2 CH.sub.2 CH.sub.2 OH " " "3-C.sub.6 H.sub.4o-CONH.sub.2 6-CH.sub.3 " CH.sub.2 CH.sub.2 CH.sub.2 "3-C.sub.6 H.sub.4o-CN " " CH.sub.2 CH.sub. 2 "3-SCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5 " " " "3-SO.sub.2 C.sub.4 H.sub.9n " " " "3-SO.sub.2 CH.sub.2 CH.sub.2 COOCH.sub.3 " " " "3-SO.sub.2 CH.sub.2 COOCH.sub.3 " " " "3-SO.sub.2 C.sub.6 H.sub.11 " " " "3-SO.sub.2 CH.sub.2 CH.sub.3 " " " "3-SO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 " H CH.sub.2 CH(CH.sub.3) "3-SCH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4 OH " CH.sub.3 CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.su b.2 CH.sub.2 K.sup.+3-SCH.sub.2 CH.sub.3 " " CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH.su b.2 CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub. 2 SO.sub.2 N(C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.11)CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3)CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.11)CH.sub.2 CH.sub.2 "3-C.sub.6 H.sub.5 " " CH.sub.2 CH(Cl)CH.sub.2 "" " " CH.sub.2 CH(OH)CH.sub.2 "" " " CH.sub.2 CH(CH.sub.2 OCH.sub.3) "" " " CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5) "" " " CH.sub.2 CH(OCOCH.sub.3)CH.sub.2 "" " " CH.sub.2 CH.sub.2 NHCOCH.sub.2 "" " " CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4 "" " " CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 NHCONHCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 N(COC.sub.6 H.sub.5)CH.su b.2 CH.sub.2 "__________________________________________________________________________
TABLE 7__________________________________________________________________________ ##STR35##R (R.sub.1).sub.m R.sub.2 Z M__________________________________________________________________________3-CH.sub.3, 4-Br 2-CH.sub.3 H CH.sub.2 CH.sub.2 K.sup.+" 2-Cl " " "" 2,5-di-Cl " " "" 2,5-di-CH.sub.3 " " "" 2,5-di-OCH.sub.3 " " "" 3-OCH.sub.3 C.sub.2 H.sub.5 " "" 2-OCH.sub.3, 5-NHCOCH.sub.3 H " "" 2-CH.sub.3, 3-Cl " " "" 2-OCH.sub.3, 5-Cl " " "" 3-NHCOCH.sub.3 C.sub.2 H.sub. 5 " "" 3-NHCOC.sub.2 H.sub.5 C.sub.2 H.sub.4 OCH.sub.3 " "" 3-NHCOCH.sub.2 OH CH.sub.2 C.sub.6 H.sub.5 " "" 3-NHCOCH.sub.2 OCH.sub.3 C.sub.6 H.sub.11 " "" 3-NHCOC.sub.6 H.sub.5 CH.sub.2 C.sub.6 H.sub.11 " "" 3-NHCOOC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5 " "3-CH.sub.34-Cl 3-NHCONHC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OH " "" 3-NHCOC.sub.6 H.sub.11 CH.sub.2 CH(CH.sub.3).sub.2 " "" 3-NHCOCH.sub.2 CN CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 " "" 3-NHCOCH.sub.2 OC.sub.6 H.sub.5 CH.sub.2 CH.sub.2 OCOCH.sub.3 " "3-CH.sub.34-CN 3-NHCOCH.sub.2 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 CONH.sub.2 " "3-CH.sub.34-COOC.sub.2 H.sub.5 3-CH.sub.3 CH.sub.2 CH.sub.2 NHCOCH.sub.3 " "" " CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3 " "" " CH.sub.2 CH.sub.2 SO.sub.2 NH.sub.2 " "" " CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3 " "3-CH.sub.34-SCH.sub.2 CHCH.sub.2 " CH.sub.2 CH.sub.2 SCH.sub.3 " "" " ##STR36## CH.sub.2 CH.sub.2 CH.sub.2 Na.sup.+" " ##STR37## " "3-CH.sub.34-SO.sub.2 C.sub.2 H.sub.5 3-OC.sub.6 H.sub.5 ##STR38## " NH.sub.4.sup.+3-CH.sub.34-SC.sub.6 H.sub.11 3-CH.sub.3 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 Na.sup.+3-CH.sub.34-OC.sub.2 H.sub.5 " ##STR39## CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5) "3-CL4-CN " CH.sub.2 CH.sub.2 COOCH.sub.3 CH.sub.2 CH(C.sub.6 H.sub.5) "3-CH.sub.34-SCN " CH.sub.2 CH.sub.2 CN CH.sub.2 CH(CH.sub.3) "3-Br4-COOCH.sub.3 " C.sub.2 H.sub.5 CH.sub.2 CH(OH)CH.sub.2 "3-CH.sub.34-COOC.sub.2 H.sub.5 2-CH.sub.3 S H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 "3-CH.sub.34-CONH.sub.2 3-CH.sub.3 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5 CH.sub.2 CH(OCOCH.sub.3)CH.sub.2 "3-CH.sub.34-CONHC.sub.2 H.sub.4 OH " CH.sub.2 CH(OH)CH.sub.2 Cl CH.sub.2 CH.sub.2 "3-CH.sub.34-CONHC.sub.4 H.sub.9n 2-OCH.sub.3, 5-CH.sub.3 C.sub.2 H.sub.5 " "3-CH.sub.34-OC.sub.6 H.sub.5 " H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 "3-CH.sub.34-OC.sub.6 H.sub.4p-CH.sub.3 " H " "3-CH.sub.34-SC.sub.6 H.sub.5 " " CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 K.sup.+3-CH.sub.34-SCH.sub.2 CH.sub.2 OH 3-CH.sub.3 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 "3-CH.sub.34-SCH.sub.2 CH.sub.3 " " CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 " ##STR40## " " CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 "3-CH.sub.34-Br " " CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 N(COCH.sub.3)CH. sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4 "" " " CH.sub.2 CH.sub.2 NHCOCH.sub.2 "" " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "3-CH.sub.34-CONH.sub.2 " " CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 "3-CH.sub.34-CONHC.sub.3 H.sub.6 OCH.sub.3 " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "3-CH.sub.34-Cl " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.11)CH.sub.2 "H.sub.2" " " CH.sub.2 CH.sub.2 N(COCH.sub.3)CH. sub.2 CH.sub.2 "" " " CH.sub.2 CH(CH.sub.2 OCH.sub.3) "" " " CH.sub.2 CH(Cl)CH.sub.2 "" " " CH.sub.2 CH.sub.2 NHCONHC.sub.2 H.sub.4 "" " " CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2 "__________________________________________________________________________
TABLE 8__________________________________________________________________________ ##STR41##R (R.sub.1).sub.m R.sub.3 R.sub.4 Z M__________________________________________________________________________3-CH.sub.34-Br H CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 K.sup.+" 7-CH.sub.3 " " " "" 7-OCH.sub.3 " " " "" 7-Cl " " " "" 5-CH.sub.3, 8-OCH.sub.3 " " " "" 5,8-di-OCH.sub.3 " " " "" 5,8-di-CH.sub.3 " " " "" 5-Cl, 8-OCH.sub.3 " " " "" 8-OCH.sub.3 " " " "" 8-OC.sub.2 H.sub.5 H H " "" 7-CH.sub.3 " " " "3-CH.sub.34-CN 7-NHCOCH.sub.3 CH.sub.3 CH.sub.3 " Na.sup.+" 7-NHCOH " " " "" 7-NHCOCH.sub.2 OCH.sub.3 " " " "3-CH.sub.34-COOC.sub.2 H.sub.5 7-NHCOCH.sub.2 OC.sub.6 H.sub.5 H CH(CH.sub.3).sub.2 " "" 7-NHCOCH.sub.2 C.sub.6 H.sub.5 " " " "" 7-NHCOCH.sub.2 Cl " " " "3-CH.sub.3 7-NHCOC.sub.6 H.sub.5 " " " "" 7-NHCOC.sub.6 H.sub.11 CH.sub.3 CH.sub.3 " "3-CH.sub.34-Cl 7-NHCONHC.sub.2 H.sub.5 " " " "" 7-NHSO.sub.2 CH.sub.3 " " " "" 7-NHCOCH.sub.2 CN " " " "" 7-NHCOCH.sub.2 OH " " " "3-Cl4-CN 7-NHCOOC.sub.2 H.sub.5 " " CH.sub.2 CH.sub.2 CH.sub.2 "3-Br4-COOCH.sub.3 ##STR42## " " " "3-CH.sub.34-COOCH.sub.3 8-OC.sub.4 H.sub.9n H " CH.sub.2 CH.sub.2 "3-CH.sub.34-CONH.sub.2 7-CH.sub.3 CH.sub.3 H " "3-CH.sub.34-CONHC.sub.2 H.sub.4 OH ##STR43## " CH.sub.3 " "3-CH.sub.34-CONHC.sub.4 H.sub.9n 7-OC.sub.2 H.sub.5 " " " "3-CH.sub.34-CONHC.sub.3 H.sub.6 OCH.sub.3 7-OC.sub.4 H.sub.9n " " " "3-CH.sub.34-COOC.sub.2 H.sub.4 OCH.sub.3 7-CH.sub.3 " H " "3-CH.sub.34-SCH.sub.2 CH.sub.2 OH " " " " "3-CH.sub.34-SCH.sub.2 CH.sub.2 OCOCH.sub.3 " " " CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 "3-CH.sub.34-SCH.sub.3 " " " CH.sub.2 CH.sub.2 "3-CH.sub.34-SO.sub.2 CH.sub.3 " " " " "3-CH.sub.34-SC.sub.6 H.sub.5 " " " " "3-CH.sub.34-SC.sub.6 H.sub.4p-C(CH.sub.3).sub.3 " " " CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 K.sup.+3-CH.sub.24-SC.sub.6 H.sub.4p-Cl " " " CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 " ##STR44## " " " CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 " ##STR45## " " " CH.sub.2 CH(C.sub.6 H.sub.5) " ##STR46## " " " CH.sub.2 CH(CH.sub.3) "3-CH.sub.34-SC.sub.6 H.sub.11 " " " CH.sub.2 CH(OH)CH.sub.2 "3-CH.sub.34-SCN " " " CH.sub.2 CH(Cl)CH.sub.2 "3-CH.sub.34-OC.sub.6 H.sub.5 " " " CH.sub.2 CH(CH.sub.2 OCH.sub.2 CH.sub.3) "3-CH.sub.34-OC.sub.2 H.sub.5 " " " CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5) "3-CH.sub.34-SCH.sub.2 CHCH.sub.2 " " " CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 "3-CH.sub.34-Br " " " CH.sub. 2 CH.sub.2 CH.sub.2 NHSO.sub. 2 CH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 NHCOCH.sub.2 "" " " " CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 CONHC.sub.2 ".sub.4" " " " CH.sub.2 CH.sub.2 NHCONHC.sub.2 H.sub.4 "" " " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub .2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub. 5)CH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3 )CH.sub.2 CH.sub.2 "__________________________________________________________________________
TABLE 9__________________________________________________________________________ ##STR47##R (R.sub.1).sub.m R.sub.3 Z M__________________________________________________________________________3-CH.sub.34-Cl 6-CH.sub.3 H CH.sub.2 CH.sub.2 K.sup.+" H H " "" " CH.sub.3 " "" 6-CH.sub.3 " " "3-Cl4-CN " " CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 "" 6-OCH.sub.3 " " "3-CH.sub.3 " " CH.sub.2 CH.sub.2 "3-CH.sub.34-COOC.sub.2 H.sub.5 6-CH.sub.3 " CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 "3-CH.sub.34-CONH.sub.2 " " CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 "3-CH.sub.34-CONHC.sub.2 H.sub.4 OH " " CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 "3-CH.sub.34-CONHC.sub.4 H.sub.9n " " CH.sub.2 CH(CH.sub.3) "3-CH.sub.34-CONHC.sub.3 H.sub.6 OCH.sub.3 " " CH.sub.2 CH(C.sub.6 H.sub.5) "3-CH.sub.34-CO.sub.2 CH.sub.2 H.sub.2 OCH.sub.3 6-OC.sub.2 H.sub.5 " CH.sub.2 CH.sub.2 "3-CH.sub.34-CONHCH.sub.3 6-NHCOCH.sub.3 " " Na.sup.+3-CH.sub.34-Br 6-NHCOH " " "" 6-NHCOCH.sub.2 CH.sub.2 OCH.sub.3 " " "" 6-NHCOCH.sub.2 Cl " " "" 6-NHCOCH.sub.2 CN " " "" 6-NHCOCH.sub.2 CONH.sub.2 " " "" 6-NHCOCH.sub.2 OC.sub.6 H.sub.5 " " "3-CH.sub.34-SC.sub.2 H.sub.5 6-NHCOOC.sub.2 H.sub.5 " " "3-CH.sub.34-SCH.sub.2 CH.sub.2 OH 6-NHCONHC.sub.2 H.sub.5 " " "3-CH.sub.34-SCH.sub.2 CHCH.sub.2 6-NHCOC.sub.6 H.sub.5 " " "3-CH.sub.34-SCH.sub.2 CH.sub.2 OCOCH.sub.3 6-NHCOC.sub.6 H.sub.11 " " "3-CH.sub.34-SC.sub.6 H.sub.5 6-NHSO.sub.2 CH.sub.3 " " "3-CH.sub.34-SC.sub.6 H.sub.4p-C(CH.sub.3).sub.2 6-NHCOCH.sub.2 CH.sub.2 OCOCH.sub.3 " " "3-CH.sub.34-SC.sub.6 H.sub.11 ##STR48## " " "3-CH.sub.34-SO.sub.2 CH.sub.2 CH.sub.2 OH 6-NHCOCH.sub.2 CH.sub.2 CH.sub.2 OH " " "3-CH.sub.34-SO.sub.2 CH.sub.2 CH.sub.3 6-CH.sub.3 " CH.sub.2 CH.sub.2 CH.sub.2 "3-CH.sub.34-OC.sub.6 H.sub.5 " " CH.sub.2 CH.sub.2 "3-CH.sub.34-OC.sub.6 H.sub.4p-OCH.sub.3 " " " " ##STR49## " " " " ##STR50## " " " " ##STR51## " " " "3-CH.sub.34-SCH.sub.2 CH(OH)CH.sub.2 OH " " " "3-CH.sub.34-SCH.sub.2 COOCH.sub.3 " " " "3-CH.sub.34-OC.sub.2 H.sub.5 " H CH.sub.2 CH(CH.sub.3) "3-CH.sub.34-Br " CH.sub.3 CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 K.sup.+" " " CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3 )CH.sub.2 CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.11)CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub.2 "H.sub.2" " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3)CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.11)CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH(Cl)CH.sub.2 "" " " CH.sub.2 CH(OH)CH.sub.2 "" " " CH.sub.2 CH(CH.sub.2 OCH.sub.3) "" " " CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5) "" " " CH.sub.2 CH(OCOCH.sub.3)CH.sub.2 "" " " CH.sub.2 CH.sub.2 NHCOCH.sub.2 "" " " CH.sub.2 CH.sub.2 CONHC.sub.2 ".sub.4" " " CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 NHCONHCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub .2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 N(COC.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "__________________________________________________________________________
TABLE 10__________________________________________________________________________ ##STR52##A R (R.sub.1).sub.m R.sub.2 Z M__________________________________________________________________________H 4-CN 2-CH.sub.3 H CH.sub.2 CH.sub.2 K.sup.+" " 2-Cl " " "" " 2,5-di-Cl " " "" " 2,5-di-CH.sub.3 " " "" " 2,5-di-OCH.sub.3 " " "" " 3-OCH.sub.3 C.sub.2 H.sub.5 " "" " 2-OCH.sub.3, H " " 5-NHCOCH.sub.3" " 2-CH.sub.3, 3-Cl " " "" " 2-OCH.sub. 3, 5-Cl " " "" " 3-NHCOCH.sub.3 C.sub.2 H.sub.5 " "" " 3-NHCOC.sub.2 H.sub.5 C.sub.2 H.sub.4 OCH.sub.3 " "" " 3-NHCOCH.sub.2 OH CH.sub.2 C.sub.6 H.sub.5 " "" " 3-NHCOCH.sub.2 OCH.sub.3 C.sub.6 H.sub.11 " "" " 3-NHCOC.sub.6 H.sub.5 CH.sub.2 C.sub.6 H.sub.11 " "" " 3-NHCOOC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5 " "" " 3-NHCONHC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OH " "C.sub.6 H.sub.5 3-SC.sub.2 H.sub.54-CN 3-NHCOC.sub.6 H.sub.11 CH.sub.2 CH(CH.sub.3).sub.2 " "" 3-SC.sub.2 H.sub.54-COOCH.sub.3 3-NHCOCH.sub.2 CN CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 " "" 3-SC.sub.2 H.sub.54-CONH.sub.2 3-NHCOCH.sub.2 OC.sub.6 H.sub.5 CH.sub. 2 CH.sub.2 OCOCH.sub.3 " "" 3-SCH.sub.34-CN 3-NHCOCH.sub.2 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 CONH.sub.2 " "" " 3-CH.sub.3 CH.sub.2 CH.sub.2 NHCOCH.sub.3 " "" " " CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3 " "" " " CH.sub.2 CH.sub.2 SO.sub.2 NH.sub.2 " "SO.sub.2 C.sub.6 H.sub.5 " " CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3 " "COCH.sub.3 4-CN " CH.sub.2 CH.sub.2 SCH.sub.3 " "H " " ##STR53## CH.sub.2 CH.sub.2 CH.sub.2 Na.sup.+" " " ##STR54## " "" " 3-OC.sub. 6 H.sub.5 ##STR55## " NH.sub.4.sup.+COOC.sub.2 H.sub.5 " 3-CH.sub.3 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 Na.sup.+H " " ##STR56## CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5) "CH.sub.3 4-CN " CH.sub.2 CH.sub.2 COOCH.sub.3 CH.sub.2 CH(C.sub.6 H.sub.5) "" 4-COOCH.sub.3 " CH.sub.2 CH.sub.2 CN CH.sub.2 CH(CH.sub.3) "" 4-CONH.sub.2 " C.sub.2 H.sub.5 CH.sub.2 CH(OH)CH.sub.2 "CH.sub.2 CH.sub.3 4-CN 2-CH.sub.3 S H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 "C.sub.6 H.sub.5 " 3-CH.sub.3 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5 CH.sub.2 CH(OCOCH.sub.3)CH.sub.2 "" 4-COOCH.sub.3 " CH.sub.2 CH(OH)CH.sub.2 Cl CH.sub.2 CH.sub.2 "C.sub.6 H.sub.4p-Cl " 2-OCH.sub.3, 5-CH.sub.3 C.sub.2 H.sub.5 " "C.sub.6 H.sub.4o-CH.sub.3 " " H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 "C.sub.6 H.sub.5 " " H " "" " " " CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 K.sup.+H 4-CONHC.sub.2 H.sub.4 OH 3-CH.sub.3 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 "" 4-CONHC.sub.4 H.sub.9n " " CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 "" 4-COOC.sub.2 H.sub.4 OCH.sub.3 " " CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.2 CH.sub. 2 CH.sub.2 CH.sub.2 "" 4-CONHC.sub.3 H.sub.6 OCH.sub.3 " " CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2 CH.sub.2 "" 4-CN " " CH.sub.2 CH.sub.2 N(COCH.sub.3)C H.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4 "" " " " CH.sub.2 CH.sub.2 NHCOCH.sub.2 "" " " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "SO.sub.2 CH.sub.3 4-CN " " CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 "SO.sub.2 C.sub.6 H.sub.5 " " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "SO.sub.2 CH.sub.2 CH.sub.3 " " " CH.sub. 2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.11)CH.sub.2 CH.sub.2 "H " " " CH.sub.2 CH.sub.2 N(COCH.sub.3)C H.sub.2 CH.sub.2 "" " " " CH.sub.2 CH(CH.sub.2 OCH.sub.3) "" " " " CH.sub.2 CH(Cl)CH.sub.2 "" " " " CH.sub.2 CH.sub.2 NHCONHC.sub.2 H.sub.4 "" " " " CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2 "__________________________________________________________________________
TABLE 11__________________________________________________________________________ ##STR57##A R (R.sub.1).sub.m R.sub.3 R.sub.4 Z M__________________________________________________________________________H 4-CN H CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 K.sup.+" " 7-CH.sub.3 " " " "" " 7-OCH.sub.3 " " " "" " 7-Cl " " " "" " 5-CH.sub.3, 8-OCH.sub.3 " " " "" " 5,8-di-OCH.sub.3 " " " "" " 5,8-di-CH.sub.3 " " " "" " 5-Cl, 8-OCH.sub.3 " " " "" " 8-OCH.sub.3 " " " "" " 8-OC.sub.2 H.sub.5 H H " "" " 7-CH.sub.3 " " " "CH.sub.3 " 7-NHCOCH.sub.3 CH.sub.3 CH.sub.3 " Na.sup.+" " 7-NHCOH " " " "H 4-COOCH.sub.3 7-NHCOCH.sub.2 OCH.sub.3 " " " "" 4-COOC.sub.2 H.sub.5 7-NHCOCH.sub.2 OC.sub.6 H.sub.5 H CH(CH.sub.3).sub.2 " "" 4-COOC.sub.2 H.sub.4 OCH.sub.3 7-NHCOCH.sub.2 C.sub.6 H.sub.5 " " " "" 4-CONH.sub.2 7-NHCOCH.sub.2 Cl " " " "" 4-CONHC.sub.2 H.sub.5 7-NHCOC.sub.6 H.sub.5 " " " "" " 7-NHCOC.sub.6 H.sub.11 CH.sub.3 CH.sub.3 " "" " 7-NHCONHC.sub.2 H.sub.5 " " " "C.sub.6 H.sub.5 4-CN 7-NHSO.sub.2 CH.sub.3 " " " "" " 7-NHCOCH.sub.2 CN " " " "C.sub.6 H.sub.4p-Cl " 7-NHCOCH.sub.2 OH " " " "C.sub.6 H.sub.4p-CH.sub.3 " 7-NHCOOC.sub.2 H.sub.5 " " CH.sub.2 CH.sub.2 CH.sub.2 "SO.sub.2 CH.sub.3 " ##STR58## " " " "" 4-COOCH.sub.3 8-OC.sub.4 H.sub.9n H " CH.sub.2 CH.sub.2 "SO.sub.2 C.sub.6 H.sub.5 " 7-CH.sub.3 CH.sub.3 H " "" 4-CN ##STR59## " CH.sub.3 " "" 4-CONHC.sub.2 H.sub.4 OH 7-OC.sub.2 H.sub.5 " " " "" 4-COOCH(CH.sub.3).sub.2 7-OC.sub.4 H.sub.9n " " " "CH.sub.3 3-SC.sub.2 H.sub.54-CN 7-CH.sub.3 " H " "C.sub.6 H.sub.5 " " " " " "" 3-SC.sub.2 H.sub.54-COOCH.sub.3 " " " CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 "" 3-SCH.sub.34-COOC.sub.2 H.sub.5 " " " CH.sub.2 CH.sub.2 "" 3-SO.sub.2 CH.sub.34-COOCH.sub.3 " " " " "" 3-SC.sub.6 H.sub.54-COOCH.sub.3 " " " " "COCH.sub.3 4-CN " " " CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 K.sup.+" 4-COOCH.sub.3 " " " CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 "CH.sub.2 CH.sub.2 OH " " " " CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 "H 3-CH.sub.2 CN4-CN " " " CH.sub.2 CH(C.sub.6 H.sub.5) "" 3-CH.sub.2 CONH.sub.24-CN " " " CH.sub.2 CH(CH.sub.3) "" 4-CN " " " CH.sub.2 CH(OH)CH.sub.2 "" " " " " CH.sub.2 CH(Cl)CH.sub.2 "" " " " " CH.sub.2 CH(CH.sub.2 OCH.sub.2 CH.sub.3) "" " " " " CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5) "" " " " " CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 "" " " " " CH.sub.2 CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.2 CH.sub.2 "" " " " " CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2 CH.sub.2 "" " " " " CH.sub.2 CH.sub.2 NHCOCH.sub.3 "" " " " " CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2 "" " " " " CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2 "" " " " " CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4 "" " " " " CH.sub.2 CH.sub.2 NHCONHC.sub.2 H.sub.4 "" " " " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "" " " " " CH.sub.2 CH.sub.2 N(COCH.sub.3) CH.sub.2 CH.sub.2 "" " " " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.5 )CH.sub.2 CH.sub.2 "" " " " " CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 "__________________________________________________________________________
TABLE 12__________________________________________________________________________ ##STR60##A R (R.sub.1).sub.m R.sub.3 Z M__________________________________________________________________________H 4-CN 6-CH.sub.3 H CH.sub.2 CH.sub.2 K.sup.+" " H " " "CH.sub.3 " " CH.sub.3 " "" 4-COOCH.sub.3 6-CH.sub.3 " " "" 4-COOC.sub.2 H.sub.4 OC.sub.2 H.sub.5 " " CH.sub.2 CH.sub.2 CH.sub.2 "H.sub.2" 4-CONH.sub.2 6-OCH.sub.3 " " "" 4-CONHC.sub.2 H.sub.4 OH " " CH.sub.2 CH.sub.2 "" 4-CONHC.sub.3 H.sub.6 OCH.sub.3 6-CH.sub.3 " CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 "" 4-CONHC.sub.2 H.sub.4 NHCOCH.sub.3 " " CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 "CH.sub.2 CH.sub.3 4-CN " " CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 "C.sub.6 H.sub.5 " " " CH.sub.2 CH(CH.sub.3) "" 4-COOCH.sub.2 CH.sub.3 " " CH.sub.2 CH(C.sub.6 H.sub.5) "" 4-CONH.sub.2 6-OC.sub.2 H.sub.5 " CH.sub.2 CH.sub.2 "C.sub.6 H.sub.4o-Cl " 6-NHCOCH.sub.3 " " Na.sup.+H " 6-NHCOH " " "" 4-COOCH.sub.3 6-NHCOCH.sub.2 CH.sub.2 OCH.sub.3 " " "" " 6-NHCOCH.sub.2 Cl " " "" 4-CONHC.sub. 4 H.sub.9n 6-NHCOCH.sub.2 CN " " "" " 6-NHCOCH.sub.2 CONH.sub.2 " " "" " 6-NHCOCH.sub.2 OC.sub.6 H.sub.5 " " "SO.sub.2 CH.sub.3 4-CN 6-NHCOOC.sub.2 H.sub.5 " " "" 4-COOCH.sub.3 6-NHCONHC.sub.2 H.sub.5 " " "H 3-CH.sub.2 CN4-CN 6-NHCOC.sub.6 H.sub.5 " " "C.sub.6 H.sub.5 3-SCH.sub.34-CN 6-NHCOC.sub.6 H.sub.11 " " "" 3-SCH.sub.2 CH.sub.34-CN 6-NHSO.sub.2 CH.sub.3 " " "" 3-SCH.sub.2 CH.sub.34-COOCH.sub.3 6-NHCOCH.sub.2 CH.sub.2 OCOCH.sub.3 " " "" 3-SCH.sub.34-CONHC.sub.4 H.sub.9n ##STR61## " " "SO.sub.2 C.sub.6 H.sub.5 4-CN 6-NHCOCH.sub.2 CH.sub.2 CH.sub.2 OH " " "" 4-COOCH.sub.3 6-CH.sub.3 " CH.sub.2 CH.sub.2 CH.sub.2 "SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3 4-CN " " CH.sub.2 CH.sub.2 "SO.sub.2 C.sub.4 H.sub.9n " " " " "COCH.sub.3 " " " " "COOC.sub.2 H.sub.5 " " " " "CH.sub.2 CH.sub.2 OH " " " " "C.sub.6 H.sub.4o-CH.sub.3 " " " " "" 4-COOCH.sub.3 " " " "" 4-COOCH(CH.sub.3).sub.2 " H CH.sub.2 CH(CH.sub.3) "SO.sub.2 C.sub.6 H.sub.11 " " CH.sub.3 CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 K.sup.+H 4-CN " " CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.5)CH.sub.2 "H.sub.2" " " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.11)CH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub .2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3)CH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.11)CH.sub.2 CH.sub.2 "C.sub.6 H.sub.5 " " " CH.sub.2 CH(Cl)CH.sub.2 "" " " " CH.sub.2 CH(OH)CH.sub.2 "" " " " CH.sub.2 CH(CH.sub.2 OCH.sub. ")" " " " CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5) "" " " " CH.sub.2 CH(OCOCH.sub.3)CH.sub.2 "" " " " CH.sub.2 CH.sub.2 NHCOCH.sub.2 "" " " " CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4 "" " " " CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 NHCONHCH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.s ub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 N(COC.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "__________________________________________________________________________
TABLE 13__________________________________________________________________________ ##STR62##R (R.sub.1).sub.m R.sub.2 Z M__________________________________________________________________________3,5-di-CN4-CH.sub.3 2-CH.sub.3 H CH.sub.2 CH.sub.2 K.sup.+" 2-Cl " " "" 2,5-di-Cl " " "" 2,5-di-CH.sub.3 " " "3-CN5-C.sub.6 H.sub.5 2,5-di-OCH.sub.3 " " "3-COOCH.sub.35-C.sub.6 H.sub.5 3-OCH.sub.3 C.sub.2 H.sub.5 " "3-CONH.sub.25-C.sub.6 H.sub.5 2-OCH.sub.3, 5-NHCOCH.sub.3 H " "3-CONHC.sub.2 H.sub.55-C.sub.6 H.sub.5 2-CH.sub.3, 3-Cl " " "3-COOCH.sub.3 2-OCH.sub.3, 5-Cl " " "3-CN 3-NHCOCH.sub.3 C.sub.2 H.sub.5 " "3-CN4-CH.sub.35-COOC.sub.2 H.sub.5 3-NHCOC.sub.2 H.sub.5 C.sub.2 H.sub.4 OCH.sub.3 " "" 3-NHCOCH.sub.2 OH CH.sub.2 C.sub.6 H.sub.5 " "" 3-NHCOCH.sub.2 OCH.sub.3 C.sub.6 H.sub.11 " "" 3-NHCOC.sub.6 H.sub.5 CH.sub.2 C.sub.6 H.sub.11 " "3-CN4-CH.sub.35-COCH.sub.3 3-NHCOOC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5 " "3-COOCH.sub.34-CH.sub.35-CN 3-NHCONHC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OH " "3-COOCH.sub.34-CH.sub.35-COC.sub.6 H.sub.5 3-NHCOC.sub.6 H.sub.11 CH.sub.2 CN(CH.sub.3).sub.2 " "3-COOCH.sub.35-COC.sub.6 H.sub.5 3-NHCOCH.sub.2 CN CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 " "3-COOCH.sub.35-COCH(CH.sub.3).sub.2 3-NHCOCH.sub.2 OC.sub.6 H.sub.5 CH.sub.2 CH.sub.2 OCOCH.sub.3 " "" 3-NHCOCH.sub.2 C.sub.6 H.sub.5 CH.sub.2 CH.sub. 2 CONH.sub.2 " "" 3-CH.sub.3 CH.sub.2 CH.sub.2 NHCOCH.sub.3 " "" " CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3 " "" " CH.sub.2 CH.sub.2 SO.sub.2 NH.sub.2 " "" " CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3 " "3-SO.sub.2 C.sub.6 H.sub.55-COCH.sub.3 " CH.sub.2 CH.sub.2 SCH.sub.3 " "3-SO.sub.2 CH.sub.35-CN " ##STR63## CH.sub.2 CH.sub.2 CH.sub.2 Na.sup.+3-SO.sub.2 C.sub.6 H.sub.55-Br " ##STR64## " "3,5-di-SO.sub.2 CH.sub.3 3-OC.sub.6 H.sub.5 ##STR65## " NH .sub.4.sup. +3,5-di-SO.sub.2 NH.sub.2 3-CH.sub.3 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 Na.sup.+3,5-di-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 " ##STR66## CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5) "3-CN5-COCH.sub.3 " CH.sub.2 CH.sub.2 COOCH.sub.3 CH.sub.2 CH(C.sub.6 H.sub.5) "3-CN5-COCH(CH.sub.3).sub.2 " CH.sub.2 CH.sub.2 CN CH.sub.2 CH(CH.sub.3) "3-CNSCOOC.sub.2 H.sub.5 " C.sub.2 H.sub.5 CH.sub.2 CH(OH)CH.sub.2 "3-CONH.sub.25-COOC.sub.2 H.sub.5 2-CH.sub.3 S H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 "3-CONH.sub.25-COCH(CH.sub.3).sub.2 3-CH.sub.3 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5 CH.sub.2 CH(OCOCH.sub.3)CH.sub.2 "3-CONHC.sub.2 H.sub.4 OH5-COCH(CH.sub.3).sub.2 " CH.sub.2 CH(OH)CH.sub.2 Cl CH.sub.2 CH.sub.2 "" 2-OCH.sub.3, 5-CH.sub.3 C.sub.2 H.sub.5 " "" " H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 "" " H " "" " " CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 K.sup.+3-CONHC.sub.3 H.sub.6 OCH.sub.3SCOCH(CH.sub.3).sub.2 3-CH.sub.3 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 "3-CONHC.sub.4 H.sub.9n-5-COCH(CH.sub.3).sub.2 " " CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 "3-CONCHC.sub.2 H.sub.4 OH5-COCH(CH.sub.3).sub.2 " " CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 "3-COOCH.sub.35-SO.sub.2 CH.sub.3 " " CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2 CH.sub.2 "3-CONHC.sub.2 H.sub.55-SO.sub.2 CH.sub.3 " " CH.sub.2 CH.sub.2 N(COCH.sub.3)C H.sub.2 CH.sub.2 "3-CONH.sub.25-SO.sub.2 CH.sub.3 " " CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4 "3-CONH.sub.25-SO.sub.2 C.sub.4 H.sub.9n " " CH.sub.2 CH.sub.2 NHCOCH.sub.2 "3-COOCH.sub.34-CH.sub.35-SCN " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "3-CHO4-CH.sub.3 " " CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 "3-CONH.sub.25-C.sub.6 H.sub.4p-CH.sub.3 " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "3-CN5-COOC.sub.2 H.sub.5 " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.11)CH.sub.2 CH.sub.2 "3-COOCH.sub.35-COCH(CH.sub.3).sub.2 " " CH.sub.2 CH.sub.2 N(COCH.sub.3)C H.sub.2 CH.sub.2 "" " " CH.sub.2 CH(CH.sub.2 OCH.sub.3 "" " " CH.sub.2 CH(Cl)CH.sub.2 "" " " CH.sub.2 CH.sub.2 NHCONHC.sub.2 H.sub.4 "" " " CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2 "__________________________________________________________________________
TABLE 14__________________________________________________________________________ ##STR67##R (R.sub.1).sub.m R.sub.3 R.sub.4 Z M__________________________________________________________________________3-CONHC.sub.2 H.sub.55-COCH(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 K.sup.+" 7-CH.sub.3 " " " "3-CONH.sub.25-COCH(CH.sub.3).sub.2 7-OCH.sub.3 " " " "" 7-Cl " " " "" 5-CH.sub.3, 8-OCH.sub.3 " " " "" 5,8-di-OCH.sub.3 " " " "" 5,8-di-CH.sub.3 " " " "" 5-Cl, 8-OCH.sub.3 " " " "" 8-OCH.sub.3 " " " "" 8-OC.sub.2 H.sub.5 H H " "" 7-CH.sub.3 " " " "3-COOCH.sub.35-COCH(CH.sub.3).sub.2 7-NHCOCH.sub.3 CH.sub.3 CH.sub.3 " Na.sup.+" 7-NHCOH " " " "" 7-NHCOCH.sub.2 OCH.sub.3 " " " "" 7-NHCOCH.sub.2 OC.sub.6 H.sub.5 H CH(CH.sub.3).sub.2 " "" 7-NHCOCH.sub.2 C.sub.6 H.sub.5 " " " "3,5-di-CN4-CH.sub.3 7-NHCOCH.sub.2 Cl " " " "" 7-NHCOC.sub.6 H.sub.5 " " " "" 7-NHCOC.sub.6 H.sub.11 CH.sub.3 CH.sub.3 " "" 7-NHCONHC.sub.2 H.sub.5 " " " "" 7-NHSO.sub.2 CH.sub.3 " " " "3-CONH.sub.25-C.sub.6 H.sub.5 7-NHCOCH.sub.2 CN " " " "" 7-NHCOCH.sub.2 OH " " " "3-COOCH.sub.35-C.sub.6 H.sub.5 7-NHCOOC.sub.2 H.sub.5 " " CH.sub.2 CH.sub.2 CH.sub.2 "3-COOCH.sub.35-COCH.sub.3 ##STR68## " " " "3-CN5-COOC.sub.2 H.sub.5 8-OC.sub.4 H.sub.9n H CH.sub.3 CH.sub.2 CH.sub.2 "3-CN4-CH.sub.35-COOC.sub.2 H.sub.5 7-CH.sub.3 CH.sub.3 H " "3-CN4-CH.sub.35-COCH.sub.3 ##STR69## " CH.sub.3 " "3-COOCH.sub.34-CH.sub.35-CN 7-OC.sub.2 H.sub.5 " " " "3-CN4-CH.sub.35-CO.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 7-OC.sub.4 H.sub.9n " " " "3-SO.sub.2 C.sub.6 H.sub.5 5-COCH.sub.3 7-CH.sub.3 " H " "3-SO.sub.2 C.sub.6 H.sub.4p-Cl 5-COCH.sub.3 " " " " "3-SO.sub.2 CH.sub.35-CN " " " CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 "3-COOCH.sub.35-Br " " " CH.sub.2 CH.sub.2 "3-COOCH.sub.35-SCN " " " " "3-CONHC.sub.2 H.sub.4 OH5-COCH(CH.sub.3).sub.2 " " " " "3-CONHC.sub.3 H.sub.6 OCH.sub.35-COCH(CH.sub.3).sub.2 " " " CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 K.sup.+3-CN5-SO.sub.2 CH.sub.3 " " " CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 "3,5-di-SO.sub.2 NH.sub.2 " " " CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 "3,5-di-SO.sub.2 NHC.sub.2 H.sub.5 " " " CH.sub.2 CH(C.sub.6 H.sub.5) "3-COOCH.sub.35-COC.sub.6 H.sub.5 " " " CH.sub.2 CH(CH.sub.3) "3-CONHC.sub.4 H.sub.9n-5-COC.sub.6 H.sub.5 " " " CH.sub.2 CH(OH)CH.sub.2 "3-COOCH.sub.35-SO.sub.2 CH.sub.3 " " " CH.sub.2 CH(Cl)CH.sub.2 "3-CONHC.sub.2 H.sub.4 OH5-SO.sub.2 CH.sub.3 " " " CH.sub.2 CH(CH.sub.2 OCH.sub.2 CH.sub.3) "3-CHO " " " CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5)3-SO.sub.2 C.sub.6 H.sub.5 " " " CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.23-CONHC.sub.2 H.sub.55-COCH(CH.sub.3).sub.2 " " " CH.sub.2 CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 NHCOCH.sub.2 "" " " " CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4 "" " " " CH.sub.2 CH.sub.2 NHCONHC.sub.2 H.sub.4 "" " " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 N(COCH.sub.3) CH.sub.2 CH.sub.2 "3-COOCH.sub. 34-CH.sub. 35-CONH.sub. 2 " " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "" " " " CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 "__________________________________________________________________________
TABLE 15__________________________________________________________________________ ##STR70##R (R.sub.1).sub.m R.sub.3 Z M__________________________________________________________________________3-COOCH.sub. 35-COCH(CH.sub. 3).sub.2 6-CH.sub. 3 H CH.sub.2 CH.sub.2 K.sup.+3-CONH.sub. 25-COCH(CH.sub. 3).sub.2 H H " "3-CN 5-COCH(CH.sub. 3).sub.2 " CH.sub.3 " "" 6-CH.sub. 3 " " "3-CONH.sub. 25-C.sub. 6 H.sub.5 " " CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 "" 6-OCH.sub. 3 " " "" " " CH.sub. 2 CH.sub.2 "3-CN 5-C.sub. 6 H.sub.5 6-CH.sub. 3 " CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 "3-CONHC.sub. 2 H.sub.4 OH5-C.sub. 6 H.sub.5 " " CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 "3-CONHC.sub. 2 H.sub.55-COC.sub. 6 H.sub.5 " " CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 "3-CONHCH.sub. 35-COC.sub. 6 H.sub.5 " " CH.sub.2 CH(CH.sub.3) "3-CN 4-CH.sub. 35-COOC.sub. 2 H.sub.5 " " CH.sub.2 CH(C.sub.6 H.sub.5) "3-CN 4-CH.sub. 35-COOC.sub. 2 H.sub.4 OCH.sub.3 6-OC.sub. 2 H.sub.5 " CH.sub.2 CH.sub.2 "3-CHO 4,5-di-CH.sub. 3 6-NHCOCH.sub. 3 " " Na.sup.+3-CN 4-CH.sub. 35-SCH.sub. 3 6-NHCOH " " "3-COOCH.sub. 34-CH.sub. 35-CONH.sub. 2 6-NHCOCH.sub. "2 CH.sub.2 OCH.sub.3 " "3-CONH.sub. 24-CH.sub. 35-CN 6-NHCOCH.sub. 2 Cl " " "3,5-di-CN4-CH.sub. 3 6-NHCOCH.sub. 2 CN " " "" 6-NHCOCH.sub. 2 CONH.sub.2 " " "" 6-NHCOCH.sub. 2 OC.sub.6 H.sub.5 " " "" 6-NHCOOC.sub. 2 H.sub.5 " " "3-CONH.sub. 24-CH.sub. 35-COOCH.sub. 3 6-NHCONHC.sub. 2 H.sub.5 " " "3-SO.sub. 2 CH.sub.35-COCH.sub. 3 6-NHCOC.sub. 6 H.sub.5 " " "3-SO.sub. 2 C.sub.6 H.sub.55-COCH.sub.3 6-NHCOC.sub. 6 H.sub.11 " " "3-SO.sub. 2 C.sub.6 H.sub.4p-Cl 5-COCH.sub. 3 6-NHSO.sub. 2 CH.sub.3 " " "3-SO.sub. 2 CH.sub.35-Br 6-NHCOCH.sub. 2 CH.sub.2 OCOCH.sub.3 " " "3,5-di-SO.sub. 2 CH.sub.3 ##STR71## " " "3,5-di-SO.sub. 2 NH.sub.2 6-NHCOCH.sub.2 CH.sub.2 CH.sub.2 OH " " "3,5-di-SO.sub. 2 NHC.sub.2 H.sub.5 6-CH.sub.3 " CH.sub.2 CH.sub.2 CH.sub.2 "3-CONHC.sub. 2 H.sub.4 OH5-COCH(CH.sub. 3).sub.2 " " CH.sub.2 CH.sub.2 "3-CONHC.sub. 3 H.sub.6 OCH.sub.3 5-COCH(CH.sub.3).sub.2 " " " "3-CONHC.sub. 2 H.sub.4 NHCOCH.sub.3 " " " "3-CONHC.sub. 4 H.sub. 9n-5-C.sub.6 H.sub.5 " " " "3-CN 5-COOC.sub.2 H.sub.5 " " " "3-CN 4-CH.sub.3 5-COOCH(CH.sub.3).sub.2 " " " "3-CN 4-CH.sub.3 5-CONHC.sub.2 H.sub.5 " " " "3-CN 4-CH.sub.3 5-CONHC.sub.6 H.sub.5 " H CH.sub.2 CH(CH.sub.3) "3-CONH.sub.2 5-SO.sub.2 CH.sub.3 " CH.sub.3 CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 K.sup.+3-CONH.sub.2 5-COCH(CH.sub.3).sub.2 " " CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3 )CH.sub.2 CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6 H.sub.11)CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub.2 "H.sub.2" " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.4 p-CH.sub.3)CH.sub.2 CH.sub.2 "3-CONHC.sub.2 H.sub.5 5-COCH(CH.sub.3).sub.2 " " CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6 H.sub.11)CH.sub.2 CH.sub.2 "" " " CH.sub.2 CH(Cl)CH.sub.2 "" " " CH.sub.2 CH(OH)CH.sub.2 "" " " CH.sub.2 CH(CH.sub.2 OCH.sub.3) "" " " CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5) "" " " CH.sub.2 CH(OCOCH.sub.3)CH.sub.2 "" " " CH.sub.2 CH.sub.2 NHCOCH.sub.2 "" " " CH.sub.2 CH.sub.2 CONHC.sub.2 ".sub.4" " " CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 NHCONHCH.sub.2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub .2 CH.sub.2 "" " " CH.sub.2 CH.sub.2 N(COC.sub.6 H.sub.5)CH.sub.2 CH.sub.2 "__________________________________________________________________________
EXAMPLES 11-20
Diazotization of 5-Amino-3-ethylthio-1,2,4-thiadiazole
5-Amino-3-ethylthio-1,2,4-thiadiazole (8.05 g., 0.05 m) is diazotized exactly as described in Examples 28-37 and a 0.005 m aliquot coupled to 0.005 m portion of the couplers of Examples 1-10 in the manner previously illustrated.
EXAMPLES 21-30
Diazotization of 5-Amino-3-methyl-4-cyanoisothiazole
To 25 ml of concentrated H.sub.2 SO.sub.4 is added 3.6 g. of NaNO.sub.2 allowing the temperature to rise. The solution is cooled and 50 ml of 1:5 acid is added below 10.degree. C. Stirring is continued and 6.95 g (0.05 m) of 5-amino-3-methyl-4-cyanoisothiazole is added below 5.degree. C., followed by an additional 50 ml of 1:5 acid. After stirring at 0.degree.-5.degree. C. for 2 hrs., a 0.005 m aliquot of the diazonium salt is coupled to 0.005 m of the couplers of Examples 1-10 as previously described to produce rubine to violet dyes for polyamides.
EXAMPLES 41-50
Diazotization of 5-Amino-4-carbomethoxypyrazole
Nitrosyl sulfuric acid is prepared by adding 3.6 g. NaNO.sub.2 to 25 ml of concentrated H.sub.2 SO.sub.4. The solution is cooled and 100 ml of L;5 acid is added below 20.degree. C. After further cooling, 5-amino-4-carbomethoxypyrazole (7.05 g., 0.05 m) is added at 0.degree.-5.degree. C. and stirring continued for 2 hrs. A 0.005 m aliquot of the diazonium solution is coupled to 0.005 m. of the couplers of Examples 1-10 in the manner previously described to produce red dyes for polyamides.
EXAMPLES 51-60
Diazotization of 2-Amino-3-carbomethoxy-5-isobutyrylthiophene
To 150 g. of 60% aqueous acetic acid is added 11.35 g. (0.05 m) of 2-amino-3-carbomethoxy-5-isobutyrylthiophene at room temperature. Ten grams of concentrated onc. H.sub.2 SO.sub.4 is added and the mixture cooled to 0.degree. C. A solution of 3.6 g NaNO.sub.2 in 25 ml of conc. H.sub.2 SO.sub.4 is added below 10.degree. C. and stirring continued for 1 hr. at 0.degree.-5.degree. C. A 0.005 m aliquot of this diazonium salt is coupled to 0.005 m portions of the couplers of Examples 1-10 as previously illustrated to produce violet to reddish-blue dyes for polyamides.

Number	Name	Date
3221006	Moore	Nov 1965
3585182	Straley	Jun 1971
3639384	Weaver	Feb 1972
3762861	Weaver et al.	Oct 1973
3870696	Feeman	Mar 1975
4063881	Razavi	Dec 1977

Azo dyes derived from 5-membered heterocyclic amines and aromatic amine couplers containing sulfo groups, or salts thereof

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