Azo dyes from 1,3,4-thiadiazol-2-yl and 1,2,4-thiadiazol-5-yl moieties bearing sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on their rings

This invention concerns novel dyes in which the diazo moieties contain sulfate groups. These dyes are substantially water soluble and are particularly useful for dyeing polyamide, wool and the like, and exhibit excellent properties, including fastness to light and dyeability.

The dyes of this invention correspond to the general formula: ##STR3## wherein D is a 1,3,4-thiadiazol-2-yl or 1,2,4-thiadiazol-5-yl radical; C is the coupler portion of the molecule; X' is O, NH, N(alkyl)--, or N(aryl)--; Z is selected from straight- or branched-chain alkylene, which may be substituted, for example, with phenyl, halogen, OSO.sub.3 M, alkoxy or aryloxy groups, --CH.sub.2 (CH.sub.2).sub.m V--CH.sub.2 (CH.sub.2).sub.p --, where m is 1, 2 or 3, p is 0, 1, 2 or 3, and V is O, S, SO.sub.2, --SO.sub.2 NH--, --SO.sub.2 N(alkyl)--, SO.sub.2 N(aryl)--N(SO.sub.2 aryl)--, --NH, --NHCO--, --NHCONH, --N(SO.sub.2 alkyl), or --CON(alkyl); and M is H, Na, K or NH.sub.4.
More particularly, the dyes correspond to the formula above wherein D represents the radicals ##STR4## and the coupler C is selected from ##STR5## wherein R.sup.2 and R.sup.14 each represents up to three groups selected from hydrogen, fluorine, chlorine, bromine, alkyl, cycloalkyl, alkoxy, phenoxy, alkylthio, arylthio, and radicals having the formula --NH--X--R.sup.3 in which X is --CO--, --COO--, or --SO.sub.2 -- and R.sup.3 is selected from alkyl and alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy, and when X is --CO--, R.sup.3 also is selected from hydrogen, amino, alkylamino, alkylcarbamoyl, dialkylamino, arylamino, aryl, and furyl;
R.sup.4 and R.sup.5 are each selected from hydrogen, alkyl, aryl, cycloalkyl, R.sup.4 and R.sup.5 represent a single, combined group --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --S--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --SO.sub.2 --CH.sub.2 CH.sub.2 -- and --CH.sub.2 CH.sub.2 --R.sup.15 --CH.sub.2 CH.sub.2 -- wherein R.sup.15 is alkyl, aryl, cycloalkyl or alkanoyl, and alkyl substituted with halogen, CN, OH, alkoxy, aryloxy, alkoxyalkoxy alkanoyl, alkanoyloxy, carbamoyl, alkylcarbamoyl, sulfamoyl, alkylsulfamoyl, alkoxyalkanoyloxy, and cycloalkyl;
R.sup.8 is one or two groups each selected from hydrogen, alkyl and alkyl substituted with --CN, alkoxy, alkoxycarbonyl, alkoxycarbonyloxy, phenyl, cyclohexoxy, --OH, --Cl and Br;
R.sup.9, R.sup.10 and R.sup.11 are each selected from hydrogen, alkyl, phenyl, or phenyl substituted with 1-3 groups selected from Cl, Br, alkyl or alkoxy, alkylthio, benzylthio, cyclohexylthio, phenylthio, and substituted phenylthio;
Q and Q' are each selected from --CO--, --SO.sub.2 --, or --CN; R.sup.12 and R.sup.13 are each selected from alkyl, hydroxyalkyl, alkoxy, alkoxycarbonylamino, trifluoromethyl, phenyl or phenyl substituted with 1-3 groups selected from Cl, Br, alkyl or alkoxy, alkoxycarbonylalkyl, cyanolalkyl, amino, haloalkyl, alkylamino, alkylthio, benzylthio, cyclohexylthio, phenylthio, substituted phenylthio, phenyl substituted phenyl, benzyl, alkanoylamino, alkylsulfonamido, alkylcarboxamido, benzamido and alkoxycarbonylalkylthio; R.sup.12 and R.sup.13 may combine to form an alkylene bridge of 3 to 5 carbons, or to form an arylene or cycloalkylene radical of 5-6 carbons connecting Q and Q'; R.sup.16 and R.sup.17 are selected from hydrogen, cycloalkyl, aryl, alkyl, and alkyl substituted with alkoxy, hydroxy, alkoxyalkoxy, hydroxyalkoxy, carbamoyl, sulfamoyl, acylamido, or alkenylsulfonyl, and aryl substituted with hydroxyalkyl; e is 1 or 2; and t and t' are each 1 or zero. It is noted that when t or t' is zero, the corresponding Q or Q' group is --CN;
Each of the aliphatic portions of the above alkyl, cycloaliphatic, alkoxy, aryl, aryloxy alkanoyl and the like groups, as well as the aryl and aryloxy groups, may be substituted further with up to three of the following: hydroxy; halogen; cyano; succinimido; glutarimido; phthalimido; 2-pyrrolidono; cyclohexyl; phenyl or phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl; alkanoylamino; sulfamoyl; alkylsulfamoyl; vinylsulfonyl; acrylamido, phthalimidinyl; benzoylsulfonicimidyl; alkylsulfonamido; phenylsulfonamido; alkoxycarbonylamino; alkylcarbamoyloxy; alkoxycarbonyl; alkoxycarbonyloxy; ##STR6## wherein Y is --NH--, --NH--alkyl--, --O--, --S--, or --CH.sub.2 O--; --S--R.sup.6 wherein R.sup.6 here and above is alkyl, phenyl, phenyl substituted with halogen, alkyl, alkoxy, alkanoylamino, cyano, or alkoxycarbonyl, pyridyl, pyrimidinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, triazolyl, or ##STR7## --SO.sub.2 R.sup.3 ; --COOR.sup.3 ; --OXR.sup.3 ; --NH--X--R.sup.3 ; --X--R.sup.3 ; --OCO--R.sup.3 ; --CONR.sup.7 R.sup.7 ; --SO.sub.2 NR.sup.7 R.sup.7 ; wherein R.sup.3 and X are as defined above and each R.sup.7 is selected from H and R.sup.3 ; alkoxy; alkoxy substituted with hydroxy, cyano, alkanoyloxy, or alkoxy; phenoxy or phenoxy substituted with one or more of alkyl, alkoxy or halogen. All of the aliphatic portions of the various groups herein contain from 1-6 carbons, and are straight or branched chain.
The dyes of this invention impart yellow to blue shades on fibers, particularly polyamides, and are especially useful for dyeing polyamide (nylon) carpets, giving good fastness to light, azone, oxides of nitrogen, washing, sublimation, crocking and the like, and having good leveling, transfer, exhaustion, and build properties.
The couplers used in this invention are prepared according to known procedures. The dyes may be prepared by reacting the coupler with a diazonium salt which contains one or two carbalkoxy groups. The product is reacted first with an aminoalcohol H--X'--Z--OH (X' is NH, Z is alkylene) to convert to a N-(hydroxyalkyl)carbamyl group, or with an alkanediol H--X'--Z--OH (X' is O, Z is alkylene) to convert to a hydroxyalkoxycarbonyl group. Subsequently, the material is reacted with concentrated sulfuric acid to form the sulfate ester: ##STR8##
Alternatively, a diazotizable amine containing a hydroxyalkoxycarbonyl group or a N-(hydroxyalkyl)carbamyl group may be sulfated before diazotization and coupling: ##STR9##
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. The compounds listed in the tables below can be prepared by procedures analogous to those described above.
TABLE I__________________________________________________________________________ ##STR10##R.sup.2 R.sup.4 R.sup.5 X'Z M__________________________________________________________________________2-CH.sub.3, 5-NHCOCH.sub.3 H C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 NaH C.sub.2 H.sub.5 C.sub.2 H.sub.4 N(COCH.sub.3).sub.2 N(CH.sub.3)C.sub.2 H.sub.4 "3-CH.sub.3 C.sub.2 H.sub.4 Cl C.sub.2 H.sub.4 CN NHC.sub.2 H.sub.4 K" " " NHCH.sub.2CH(C.sub.6 H.sub.5) K3-CH.sub.3 C.sub.2 H.sub.4 OH C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 Na3-NHCOCH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 CN NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na2-OCH.sub.3, 5-NHCOCH.sub.3 C.sub. 2 H.sub.4 OCOCH.sub.3 C.sub.2 H.sub.4 OCOCH.sub.3 NHC.sub.2 H.sub.4 NH.sub.43-Cl C.sub.2 H.sub.4 OH C.sub.6 H.sub.13 OC.sub.2 H.sub.4 K2-Cl H C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 K2-CH.sub.3, 3-Cl H CH.sub.2 C.sub.6 H.sub.5 NHC.sub.3 H.sub.6 KH C.sub.2 H.sub.4 OH C.sub.2 H.sub.4 CN OC.sub.2 H.sub.4 NH.sub.4H C.sub.2 H.sub.4 OSO.sub.3 K C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 K3-CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 NHCOCH.sub.3 " "3-NHCOCH.sub.3 " C.sub.2 H.sub.4 CONH.sub.2 " "H " C.sub.2 H.sub.4 NHCOCH.sub.3 N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 Na" " H NHC.sub.2 H.sub.4H CH.sub.2 CH.sub.2OCH.sub.2 CH.sub.2 NHC.sub.2 H.sub.4 NaH CH.sub.2 CH.sub.2SCH.sub.2 CH.sub.2 NHC.sub.2 H.sub.4 NaH CH.sub.2 CH.sub.2SO.sub.2CH.sub.2 CH.sub. 2 NHC.sub.2 H.sub.4 NaH CH.sub.2 CH.sub.2NHCH.sub.2 CH.sub.2 NHC.sub.2 H.sub.4 NaH CH.sub.2 CH.sub.2NCOCH.sub.3CH.sub.2 CH.sub.2 NHC.sub.2 H.sub.4 Na3-CH.sub.3 H C.sub.2 H.sub.4 SO.sub.2 NH.sub.2 NHC.sub.2 H.sub.4 Na2-OC.sub.6 H.sub.5 C.sub.2 H.sub.4 CN C.sub.2 H.sub.4 N(COCH.sub.3).sub.2 " "2-SCH.sub.3 C.sub.2 H.sub.4 OCOCH.sub.3 C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5 NHC.sub.2 H.sub.4 K3-SC.sub.6 H.sub.5 CONH.sub.2 C.sub.2 H.sub.4 SO.sub.2 NH(C.sub.2 H.sub.5) NHCH.sub.2CH(C.sub.6 H.sub.5) K3-NHCOOCH.sub.3 C.sub.2 H.sub.4 OH C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 Na3-NHSO.sub.2 CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 CN NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na2-OCH.sub.3, 5-NHCOCH.sub.3 C.sub.2 H.sub.4 OCOCH.sub.3 C.sub.2 H.sub.4 OCOCH.sub.3 NHC.sub.2 H.sub.4 NH.sub.43-NHCOCH.sub.2 Cl C.sub.2 H.sub.4 OH C.sub.6 H.sub.13 OC.sub.2 H.sub.4 K3-NHCOC.sub.2 H.sub.4 OH H C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 K2-CH.sub.3, 3-Cl H CH.sub.2 C.sub.6 H.sub.5 NHC.sub.3 H.sub.6 K2-NHCONHC.sub.2 H.sub.5 C.sub.2 H.sub.4 OH C.sub.2 H.sub.4 CN OC.sub.2 H.sub.4 NH.sub.42-NHCON(C.sub.2 H.sub.5).sub.2 C.sub.2 H.sub.4 OSO.sub.3 K C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 K3-CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 NHCOCH.sub.3 " "3-NHCOCH.sub.3 " C.sub.2 H.sub.4 CONH.sub.2 " "H " C.sub.2 H.sub.4 NHCOCH.sub.3 " Na__________________________________________________________________________
TABLE 2__________________________________________________________________________ ##STR11##R.sup.2 R.sup.8 R.sup.4 X'Z M__________________________________________________________________________7-CH.sub.3 2-CH.sub.3 C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 Na7-CH.sub.3 2-CH.sub.3 C.sub.2 H.sub.4 OSO.sub.3 K NHC.sub.2 H.sub.4 KH H C.sub.2 H.sub.4 OC.sub.6 H.sub.11 OC.sub.2 H.sub.4 Na5-CH.sub.3 H C.sub.4 H.sub.9 NHC.sub.2 H.sub.4 Na7-CH.sub.3 2-CH.sub.3 C.sub.2 H.sub.4 NHCOCH.sub.3 " "7-CH.sub.3 2,2,4-(CH.sub.3).sub.3 " N(C.sub.2 H.sub.5)C.sub.2 H.sub.4 "8-CH.sub.3 H C.sub.2 H.sub.4 Cl OC.sub.2 H.sub.4 NH.sub.4H 2,2,4-(CH.sub.3).sub.3 C.sub.2 H.sub.4 OCH.sub.3 OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 K7-NHCOCH.sub.3 " C.sub.2 H.sub.4 Br NHC.sub.2 H.sub.4 K" 5-CH.sub.3 CH.sub.2 CHOHCH.sub.2 OH OC.sub.2 H.sub.4 K7-CH.sub.3 2-CH.sub.3 CH.sub.3 NHC.sub.2 H.sub.4 K7-C.sub.6 H.sub.11 3-OH C.sub.2 H.sub.4 SO.sub.2 NH.sub.2 NHC.sub.2 H.sub.4 Na7-OC.sub.6 H.sub.5 3-CN C.sub.2 H.sub.4 N(COCH.sub.3).sub.2 N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 "7-SCH.sub.3 3-OCOCH.sub.3 C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5 NHC.sub.2 H.sub.4 K7-SC.sub.6 H.sub.5 2-CH.sub.3 C.sub.2 H.sub.4 SO.sub.2 NH(C.sub.2 H.sub.5) NHCH.sub.2CH(C.sub.6 H.sub.5) K7-NHCOOCH.sub.3 " C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 Na7-NHSO.sub.2 CH.sub.3 2-C.sub.2 H.sub.5 C.sub.2 H.sub.4 CN NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na7-OCH.sub.3 3-OCOCH.sub.3 C.sub.2 H.sub.4 OCOCH.sub.3 NHC.sub.2 H.sub.4 NH.sub.47-NHCOCH.sub. 2 Cl 3-OH C.sub.6 H.sub.13 OC.sub.2 H.sub.4 K7-NHCOC.sub.2 H.sub.4 OH 3-CONH.sub.2 C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 K7-CH.sub.3, 5-Cl 3-Cl CH.sub.2 C.sub.6 H.sub.5 NHC.sub.3 H.sub.6 K7-NHCONHC.sub.2 H.sub.5 3-OC.sub.6 H.sub.5 C.sub.2 H.sub.4 CN OC.sub.2 H.sub.4 NH.sub.47-NHCON(C.sub.2 H.sub.5).sub.2 3-OC.sub.6 H.sub.5 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 K7-CH.sub.3 3-SC.sub.2 H.sub.5 C.sub.2 H.sub.4 NHCOCH.sub.3 " "7-NHCOCH.sub.3 3-CONHC.sub.2 H.sub.5 C.sub.2 H.sub.4 CONH.sub.2 " "H 3-OCH.sub.3 C.sub.2 H.sub.4 NHCOCH.sub.3 " Na__________________________________________________________________________
TABLE 3__________________________________________________________________________ ##STR12##R.sup.2 R.sup.8 R.sup.4 X'Z M__________________________________________________________________________6-NHCOCH.sub.3 3-CH.sub.3 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 Na6-CH.sub.3 3-CH.sub.3 C.sub.2 H.sub.5 OC.sub.2 H.sub.4 Na6-Cl " C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 K6-Br 2,3-di-CH.sub.3 C.sub.2 H.sub.4 SO.sub.2 NH.sub.2 " NH.sub.46-F 3-CH.sub.3 " NHC.sub.2 H.sub.4 KH 2-CH.sub.2 OH CH(CH.sub.3).sub.2 " "H 2-CH.sub.2 OH " N(CH.sub.3)C.sub.2 H.sub.4 "6-NHCOCH.sub.3 2-CH.sub.2 Cl C.sub.2 H.sub.5 NHC.sub.3 H.sub.6 Na" 3-CH(CH.sub.3).sub.2 C.sub.2 H.sub.4 OCH.sub.3 NHC.sub.2 H.sub.4 Na6-CH.sub.3 3-CH.sub.3 " " Na6-C.sub.6 H.sub.11 2-CH.sub.2 OC.sub.6 H.sub.5 C.sub.2 H.sub.4 SO.sub.2 NH.sub.2 NHC.sub.2 H.sub.4 Na6-OC.sub.6 H.sub.5 2-CH.sub.2 OC.sub.2 H.sub.5 C.sub.2 H.sub.4 N(COCH.sub.3).sub.2 " "6-SCH.sub.3 ##STR13## C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5 NHC.sub.2 H.sub.4 K6-SC.sub.6 H.sub.5 2-CH.sub.2 Cl C.sub.2 H.sub.4 SO.sub.2 NH(C.sub.2 H.sub.5) NHCH.sub.2CH(C.sub.6 H.sub.5) K6-NHCOOCH.sub.3 2-CH.sub.2 OH C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 Na6-NHSO.sub.2 CH.sub.3 " C.sub.2 H.sub.4 CN NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na8-OCH.sub.3, 5-NHCOCH.sub.3 ##STR14## C.sub.2 H.sub.4 OCOCH.sub.3 NHC.sub.2 H.sub.4 NH.sub.46-NHCOCH.sub.2 Cl " C.sub.6 H.sub.13 OC.sub.2 H.sub.4 K6-NHCOC.sub.2 H.sub.4 OH 3-C.sub.2 H.sub.5 C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 K8-CH.sub.3, 5-Cl " CH.sub.2 C.sub.6 H.sub.5 NHC.sub.3 H.sub.6 K6-NHCONHC.sub.2 H.sub.5 2-CH.sub.2 OC.sub.6 H.sub.5 C.sub.2 H.sub.4 CN OC.sub.2 H.sub.4 NH.sub.46-NHCON(C.sub.2 H.sub.5).sub.2 2-CH.sub.2 OC.sub.6 H.sub.5 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 K6-OC.sub.6 H.sub.5 H C.sub.2 H.sub.4 NHCOCH.sub.3 " "6-NHCOCH.sub.3 " C.sub.2 H.sub.4 CONH.sub.2 " "H " C.sub.2 H.sub.4 NHCOCH.sub.3 N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 Na__________________________________________________________________________
TABLE 4__________________________________________________________________________ ##STR15##R.sup.9 R.sup.2 R.sup.4 X'Z M__________________________________________________________________________C.sub.6 H.sub.5 H CH.sub.3 NHC.sub.2 H.sub.4 NaCH.sub.3 6-CH.sub.3 CH.sub.3 " "" " C.sub.6 H.sub.5 " "" H C.sub.2 H.sub.5 " "C.sub.6 H.sub.5 H H " "" " CH.sub.3 " "CH.sub.3 " CH.sub.3 N(CH.sub.3)C.sub.2 H.sub.4 "" 5-OC.sub.2 H.sub.5 " NHC.sub.3 H.sub.6 "CH.sub.3 " H NHC.sub.2 H.sub. 4 "C.sub.6 H.sub.4p-Br H H " "C.sub.6 H.sub.5 " C.sub.2 H.sub.4 CONH.sub.2 " KC.sub.6 H.sub.4p-OCH.sub.3 " C.sub.2 H.sub.4 CN N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 K" 5-C.sub.6 H.sub.11 C.sub.2 H.sub.4 SO.sub.2 NH.sub.2 NHC.sub.2 H.sub.4 "C.sub.2 H.sub.4 CN 6-OC.sub.6 H.sub.5 C.sub.2 H.sub.4 N(COCH.sub.3).sub.2 " "C.sub.2 H.sub.4 OCOCH.sub.3 6-SCH.sub.3 C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5 NHC.sub.2 H.sub.4 KCH.sub.3 6-SC.sub.6 H.sub.5 C.sub.2 H.sub.4 SO.sub.2 NH(C.sub.2 H.sub.5) NHCH.sub.2CH(C.sub.6 H.sub.5) K" 6-NHCOOCH.sub.3 C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 NaC.sub.3 H.sub.7 6-NHSO.sub.2 CH.sub.3 C.sub.2 H.sub.4 CN NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 NaCH.sub.3 6-OCH.sub.3, C.sub.2 H.sub.4 OCOCH.sub.3 NHC.sub.2 H.sub.4 NH.sub.4 5-NHCOCH.sub.3C.sub.2 H.sub.5 6-NHCOCH.sub.2 Cl C.sub.6 H.sub.13 OC.sub.2 H.sub.4 K" 6-NHCOC.sub.2 H.sub.4 OH C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 K" " CH.sub.2 C.sub.6 H.sub.5 NHC.sub.3 H.sub.6 KC.sub.2 H.sub.5 6-NHCONHC.sub.2 H.sub.5 C.sub.2 H.sub.4 CN OC.sub.2 H.sub.4 NH.sub.4C.sub.6 H.sub.4p-OCH.sub.3 6-NHCON(C.sub.2 H.sub.5).sub.2 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 KC.sub.2 H.sub.5 6-CH.sub.3 C.sub.2 H.sub.4 NHCOCH.sub.3 " "C.sub.2 H.sub.5 6-NHCOCH.sub.3 C.sub.2 H.sub.4 CONH.sub.2 " "CH.sub.3 H C.sub.2 H.sub.4 NHCOCH.sub.3 " Na" " C.sub.2 H.sub.4 Cl " "C.sub.6 H.sub.4p-CH.sub.3 6-OH " " "__________________________________________________________________________
TABLE 5______________________________________ ##STR16##R.sup.9 R.sup.10 X'Z M______________________________________C.sub.6 H.sub.5 H NHC.sub.2 H.sub.4 NaCH.sub.3 " OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 NaCH.sub.3 H OC.sub.2 H.sub.4 NaCH.sub.3 C.sub.6 H.sub.5 NHC.sub.2 H.sub.4 NaCH.sub.3 C.sub.6 H.sub.5 NHC.sub.3 H.sub.6 NaC.sub.6 H.sub.5 CH.sub.3 NHC.sub.2 H.sub.4 NaC.sub.6 H.sub.5 " " NH.sub.4" " N(C.sub.2 H.sub.5)C.sub.2 H.sub.4 "CH.sub.3 H NHC.sub.2 H.sub.4 K" H NH (CH.sub.2).sub.5 KC.sub.6 H.sub.4p-Br " OC.sub.2 H.sub.4 KC.sub.6 H.sub.4p-OCH.sub.3 " OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 K" Br NHC.sub.2 H.sub.4 KC.sub.2 H.sub.4 CN Br N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 KC.sub.2 H.sub.4 OCOCH.sub.3 Br NHC.sub.2 H.sub.4 KCH.sub.3 C.sub.2 H.sub.5 NHCH.sub.2CH(C.sub.6 H.sub.5) K" C.sub.2 H.sub.5 OC.sub.2 H.sub.4 KC.sub.3 H.sub.7 C.sub.6 H.sub.5 NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 KCH.sub.3 " NHC.sub.2 H.sub.4 KC.sub.2 H.sub.5 C.sub.6 H .sub.4p-CH.sub.3 OC.sub.2 H.sub.4 K" H OC.sub.2 H.sub.4 K" CONHC.sub.2 H.sub.5 NHC.sub.3 H.sub.6 KC.sub.2 H.sub.5 CH.sub.3 OC.sub.2 H.sub.4 KC.sub.6 H.sub.4p-OCH.sub.3 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 KC.sub.2 H.sub.5 SCN " KC.sub.2 H.sub.5 CONH.sub.2 " KCH.sub.3 CH(CH.sub.3).sub.2 " K" C.sub.6 H.sub.5 " KC.sub.6 H.sub.4p-CH.sub.3 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 OCH.sub.2 K______________________________________
TABLE 6__________________________________________________________________________ ##STR17##R.sup.4 R.sup.11 X'Z M__________________________________________________________________________H CH.sub.3 NHC.sub.2 H.sub.4 KH C.sub.6 H.sub.4p-OCH.sub.3 " "H CF.sub.3 " "H COOC.sub.2 H.sub.5 " " ##STR18## " NaH C.sub.6 H.sub.5 " KC.sub.6 H.sub.5 C.sub.6 H.sub.4p-Br " "" C(CH.sub.3).sub.3 " "" C.sub.6 H.sub.11 " Na" C.sub.6 H.sub.5 " NaC.sub.6 H.sub.5 SO.sub.2 CH.sub.3 N(CH.sub.3)C.sub.2 H.sub.4 NaC.sub.2 H.sub.5 SO.sub.2 " NHC.sub.2 H.sub.4 K ##STR19## " N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 K ##STR20## CH.sub.3 NHC.sub.2 H.sub.4 KCH.sub.3 CONH.sub.2 NHCH.sub.2CH(C.sub.6 H.sub.5) KC.sub.2 H.sub.4 OH C.sub.2 H.sub.5 OC.sub.2 H.sub.4 KC.sub.2 H.sub.4 CN " NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 KC.sub.2 H.sub.4 OCOCH.sub.3 " NHC.sub.2 H.sub.4 KC.sub.6 H.sub.11 CF.sub.3 OC.sub.2 H.sub.4 KC.sub.2 H.sub.4 OH C.sub.6 H.sub.4p-Cl OC.sub.2 H.sub.4 KCH.sub.2 C.sub.6 H.sub.5 CONHC.sub.2 H.sub.5 NHC.sub.3 H.sub.6 KC.sub.2 H.sub.4 CN CH(CH.sub.3).sub.2 OC.sub.2 H.sub.4 KC.sub.2 H.sub.5 " NHC.sub.2 H.sub.4 KC.sub.2 H.sub.4 NHCOCH.sub.3 C.sub.2 H.sub.5 " KC.sub.2 H.sub.4 CONH.sub.2 CH.sub.3 " KC.sub.2 H.sub.4 NHCOCH.sub. 3 C.sub.2 H.sub.5 " K" C.sub.6 H.sub.5 " K__________________________________________________________________________
TABLE 7______________________________________ ##STR21##Q Q' R.sup.12 R.sup.13 X'Z M______________________________________CO CO C.sub.6 H.sub.5 C.sub.6 H.sub.5 NHC.sub.2 H.sub.4 NaCO CO CH.sub.3 CH.sub.2 OH " NaCN CO -- NHCO.sub.2 C.sub.2 H.sub.5 OC.sub.2 H.sub.4 NaCN CO -- CH.sub.3 NHC.sub.2 H.sub.4 NaCO SO.sub.2 NH.sub.2 OC.sub.6 H.sub.5 " "CO SO.sub.2 CH.sub.3 OCH.sub.3 " "CN SO.sub.2 -- C.sub.6 H.sub.5 " "CO CO CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 " KCO CO 1,2-C.sub.6 H.sub.4 " KCO CO C.sub.2 H.sub.5 OC.sub.2 H.sub.5 " KCO CO CF.sub.3 H " KCO CO OCH.sub.3 H " KCO CO CH.sub.2 Cl H " KCO CO " CH.sub.3 " KCO CO NHC.sub.2 H.sub.5 NH.sub.2 N(CH.sub.3)C.sub.2 H.sub.4 KCO CO NHC.sub.2 H.sub.5 NH.sub.2 N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 KCO CO OC.sub.2 H.sub.5 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 KCO CO OCH.sub.2C.sub.6 H.sub.5 " NHC.sub.2 H.sub.4 KCO CO OC.sub.6 H.sub.11 OCH.sub.3 NHC.sub.2 H.sub.4 KCO CO C.sub.6 H.sub.5 OCH.sub.3 NHC.sub.2 H.sub.4 KCO CO NHCOC.sub.2 H.sub.5 NHCO.sub.2 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 KCO CO NHSO.sub.2 C.sub.2 H.sub.5 NHCO.sub.2 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 KCO CO NHCOC.sub.6 H.sub.5 NHCO.sub.2 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 KCO CO OC.sub.2 H.sub.5 NHCO.sub.2 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 K______________________________________
TABLE 8______________________________________ ##STR22##OHPosition R.sup.2 X'Z M______________________________________2 5-CH.sub.3 NHC.sub.2 H.sub.4 Na2 5-CH.sub.3 OC.sub.2 H.sub.4 Na2 5-OCH.sub.3 NHC.sub.2 H.sub.4 K2 5-Cl " Na2 5-Cl " Na4 3-OCH.sub.3 " K4 3-OCH.sub.3 " K3,4 H " Na4 2-NHC.sub.6 H.sub.5 " Na2 5-NHCOCH.sub.3 " Na3,4 H N(CH.sub.3)C.sub.2 H.sub.4 K ##STR23## NHC.sub.2 H.sub.4 K C.sub.2 H.sub.4 OSO.sub.3 K2 5-C.sub.6 H.sub.11 NHC.sub.2 H.sub.4 K2 5-OC.sub.6 H.sub.5 N(C.sub.6 H.sub.5 )C.sub.2 H.sub.4 "2 5-SCH.sub.3 NHC.sub.2 H.sub.4 K2 5-SC.sub.6 H.sub.5 NHCH.sub.2CH(C.sub.6 H.sub.5) Na2 5-NHCOOCH.sub.3 OC.sub.2 H.sub.4 Na2 5-NHSO.sub.2 CH.sub.3 NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na2 5-NHCOCH.sub.3 NHC.sub.2 H.sub.4 NH.sub.42 5-NHCOCH.sub.2 Cl OC.sub.2 H.sub.4 K2 5-NHCOC.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 K2 5-Cl NHC.sub.3 H.sub.6 K2 5-NHCONHC.sub.2 H.sub.5 OC.sub.2 H.sub.4 NH.sub.42 5-NHCON(C.sub.2 H.sub.5).sub.2 NHC.sub.2 H.sub.4 K2 5-CH.sub.3 " "2 5-NHCOCH.sub.3 " "4 H " Na______________________________________
TABLE 9__________________________________________________________________________ ##STR24##OHPosition R.sup.2 R.sup.14 X'Z M__________________________________________________________________________2 H 6-SO.sub.2 N(CH.sub.3).sub.2 NHC.sub.2 H.sub.4 Na2 H " " "2 3-CONH.sub.2 H " Na4 H H N(CH.sub.3)C.sub.2 H.sub.4 "4 H H OC.sub.2 H.sub.4 K2,6 H H OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 K2 H H OC.sub.2 H.sub.4 K" H 6-SO.sub.2 NHCH.sub.3 OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 K2 3-CONH.sub.2 H NHC.sub.2 H.sub.4 Na2 3-CONHC.sub.6 H.sub.5 H NHCH(C.sub. 2 H.sub.5)CH.sub.2 Na2 3-CONHC.sub.6 H.sub.4p H OC.sub.2 H.sub.4 NH.sub.4 OC.sub.2 H.sub.4 OH4 H H NHC.sub.2 H.sub.4 Na4 H H NHC.sub.2 H.sub.4 Na4 H H " "2 H H NHC.sub.2 H.sub.4 K2 " " NHCH.sub.2CH(C.sub.6 H.sub.5) K2 3-CO.sub.2 CH.sub.3 " OC.sub.2 H.sub.4 Na2 " " NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na2,4 H H NHC.sub.2 H.sub.4 NH.sub.42 3-COCH.sub.2 Cl " OC.sub.2 H.sub.4 K4 H " OC.sub.2 H.sub.4 K4 H H NHC.sub.3 H.sub.6 K4 H " OC.sub.2 H.sub.4 NH.sub.44 H " NHC.sub.2 H.sub.4 K4 H " " "2 3-CONHC.sub.6 H.sub.5 " " "2 H " N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 "__________________________________________________________________________
TABLE 10__________________________________________________________________________ ##STR25##R.sup.16 R.sup.17 R.sup.2 R.sup.14 X'Z M__________________________________________________________________________C.sub.6 H.sub.11 H H H NHC.sub.2 H.sub.4 NaC.sub.2 H.sub.4 CONH.sub.2 H H " " "C.sub.2 H.sub.4 SO.sub.2 CHCH.sub.2 H H 8-OH " NaC.sub.2 H.sub.4 NHSO.sub.2 CH.sub.3 H H H N(CH.sub.3)C.sub.2 H.sub.4 " ##STR26## H 3-OCH.sub.3 8-OH OC.sub.2 H.sub.4 KC.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3 H H H OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 KCH(CH.sub.3)C.sub.2 H.sub.5 H H H OC.sub.2 H.sub.4 KCH(CH.sub.3)CH.sub.2 CH(CH.sub.3)CH.sub.3 CH.sub.3 H H OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 KC.sub.6 H.sub.5 H 3-OCH.sub.3 H NHC.sub.2 H.sub.4 NaC.sub.2 H.sub.5 C.sub.2 H.sub.4 OH " H NHCH(C.sub.2 H.sub.5)CH.sub.2 NaCH.sub.2 CH(OH)CH.sub.2 OH " H H OC.sub.2 H.sub.4 NH.sub.4C.sub.2 H.sub.4 SO.sub.2 NH.sub.2 H H H NHC.sub.2 H.sub.4 Na(CH.sub.2).sub.3 NHCOCH.sub.3 H H H NHC.sub.2 H.sub.4 NaC.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH H H H " "C.sub.3 H.sub.6 OCH.sub.3 H H H NHC.sub.2 H.sub.4 KCH.sub.2 C.sub.6 H.sub.5 CH.sub.2 C.sub.6 H.sub.5 " " NHCH.sub.2CH(C.sub.6 H.sub.5) KC.sub.6 H.sub.11 H H " OC.sub.2 H.sub.4 NaC.sub.2 H.sub.4 CONH.sub.2 H " " NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 NaC.sub.2 H.sub.4 SO.sub.2 CHCH.sub.2 H H 8-OCH.sub.3 NHC.sub.2 H.sub.4 NH.sub.4 ##STR27## H 3-OC.sub.2 H.sub.5 8-OC.sub.2 H.sub.5 OC.sub.2 H.sub.4 K ##STR28## H H " OC.sub.2 H.sub.4 KC.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3 H H H NHC.sub.3 H.sub.6 KCH(CH.sub.3)C.sub.2 H.sub.5 H H " OC.sub.2 H.sub.4 NH.sub.4CH(CH.sub.3)CH.sub.2 CH(CH.sub.3)CH.sub.3 H H " NHC.sub.2 H.sub.4 KC.sub.6 H.sub.5 H 3-C.sub.2 H.sub.5 " " "C.sub.2 H.sub.5 " H " " "CH.sub.2 CH(OH)CH.sub.2 OH " H " N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 "__________________________________________________________________________
TABLE 11__________________________________________________________________________ ##STR29##R.sup.2 R.sup.4 R.sup.5 X'Z M__________________________________________________________________________H C.sub.2 H.sub.5 C.sub.2 H.sub.4 NHCOCH.sub.3 NHC.sub.2 H.sub.4 NaH C.sub.2 H.sub.5 C.sub.3 H.sub.7n N(CH.sub.3)C.sub.2 H.sub.4 "H " C.sub.2 H.sub.5 NHCH.sub.2CH(OSO.sub.2 Na)CH.sub.2 NaH CH.sub.3 C.sub.2 H.sub.4 SO.sub.2 CHCH.sub.2 " "H C.sub.2 H.sub.4 OH C.sub.2 H.sub.4 CN OC.sub.2 H.sub.4 K3-CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 CN OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na3-CH.sub.3 C.sub.2 H.sub.4 OH C.sub. 2 H.sub.4 OH OC.sub.2 H.sub.4 Na2-CH.sub.33-Cl H CH.sub.2 C.sub.6 H.sub.5 NHC.sub.3 H.sub.6 K3-Cl C.sub.6 H.sub.11 C.sub.2 H.sub.4 OSO.sub.3 K " K3-NHCOCH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 CN NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na" " C.sub.2 H.sub.4 CONH.sub.2 NHC.sub.2 H.sub.4 K2-CH.sub.3 H C.sub.2 H.sub.4 SO.sub.2 NH.sub.2 NHC.sub.2 H.sub.4 Na2-OC.sub.6 H.sub.5 C.sub.2 H.sub.4 CN C.sub.2 H.sub.4 N(COCH.sub.3).sub.2 N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 "3-SCH.sub.3 C.sub.2 H.sub.4 OCOCH.sub.3 C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5 NHC.sub.2 H.sub.4 K3-CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 OCOCH.sub.3 NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na3-SC.sub.6 H.sub.5 C.sub.2 H.sub.4 SO.sub.2 NH(C.sub.2 H.sub.5) NHCH.sub.2CH(C.sub.6 H.sub.5) K3-NHCOOCH.sub.3 C.sub.2 H.sub.4 OH C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 Na3-NHSO.sub.2 CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 CN NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na2-OCH.sub.3, C.sub.2 H.sub.4 OCOCH.sub.3 C.sub.2 H.sub.4 OCOCH.sub.3 NHC.sub.2 H.sub.4 NH.sub.45-NHCOCH.sub.33-NHCOCH.sub.2 Cl C.sub.2 H.sub.4 OH C.sub.6 H.sub.13 OC.sub.2 H.sub.4 K3-NHCOC.sub.2 H.sub.4 OH H C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 K2-CH.sub.3, 3-Cl H CH.sub.2 C.sub.6 H.sub.5 NHC.sub.3 H.sub.6 K2-NHCONHC.sub.2 H.sub.5 C.sub.2 H.sub.4 OH C.sub.2 H.sub.4 CN OC.sub.2 H.sub.4 NH.sub.42-NHCON(C.sub.2 H.sub.5).sub.2 C.sub.2 H.sub.4 OSO.sub.3 K C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 K3-CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 NHCOCH.sub.3 " "3-NHCOCH.sub.3 " C.sub.2 H.sub.4 CONH.sub.2 " "H " C.sub.2 H.sub.4 NHCOCH.sub.3 " NaH CH.sub.2 CH.sub.2OCH.sub.2 CH.sub.2 " NaH CH.sub.2 CH.sub.2SCH.sub.2 CH.sub. 2 " NaH CH.sub.2 CH.sub.2SO.sub.2CH.sub.2 CH.sub.2 " NaH CH.sub.2 CH.sub.2NHCH.sub.2 CH.sub.2 " NaH CH.sub.2 CH.sub.2NCOCH.sub.3CH.sub.2 CH.sub.2 " Na__________________________________________________________________________
TABLE 12__________________________________________________________________________ ##STR30##R.sup.2 R.sup.8 R.sup.4 X'Z M__________________________________________________________________________7-CH.sub.3 2-CH.sub.3 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 K" " " N(C.sub.2 H.sub.5)C.sub.2 H.sub.4 "H 2,2,4-(CH.sub.3).sub.3 C.sub.2 H.sub.5 NHC.sub.3 H.sub.6 NaH " C.sub.2 H.sub.4 OSO.sub.3 Na OC.sub.2 H.sub.4 NaH " " NHC.sub.2 H.sub.4 Na7-CH.sub.3 2-CH.sub.3 C.sub.2 H.sub.4 NHCOCH.sub.3 " "7-NHCOCH.sub.3 H C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 K" " C.sub.2 H.sub.4 OC.sub.2 H.sub.5 NHC.sub.2 H.sub.4 Na5-CH.sub.3 " " " K8-CH.sub.3 " C.sub.2 H.sub.4 OCH.sub.3 N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 NH.sub.47-CH.sub.3 2,2,4-(CH.sub.3).sub.3 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 K" " C.sub.2 H.sub.4 Cl NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 K" " " NHC.sub.2 H.sub.4 K7-SC.sub.6 H.sub.5 " C.sub.2 H.sub.4 SO.sub.2 NH(C.sub.2 H.sub.5) NHCH.sub.2CH(C.sub.6 H.sub.5) K7-NHCOOCH.sub.3 CH.sub.3 C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 Na7-NHSO.sub.2 CH.sub.3 2-C.sub.2 H.sub.5 C.sub.2 H.sub.4 CN NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na7-OCH.sub.3, 3-OCOCH.sub.3 C.sub.2 H.sub.4 OCOCH.sub.3 NHC.sub.2 H.sub.4 NH.sub.45-NHCOCH.sub.37-NHCOCH.sub.2 Cl 3-OH C.sub.6 H.sub.13 OC.sub.2 H.sub.4 K7-NHCOC.sub.2 H.sub.4 OH 3-CONH.sub.2 C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 K7-CH.sub.3, 3-Cl 3-Cl CH.sub.2 C.sub.6 H.sub.5 NHC.sub.3 H.sub.6 K7-NHCONHC.sub.2 H.sub.5 3-OC.sub.6 H.sub.5 C.sub.2 H.sub.4 CN OC.sub.2 H.sub.4 NH.sub.47-NHCON(C.sub.2 H.sub.5) " C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 K7-CH.sub.3 3-SC.sub.2 H.sub.5 C.sub.2 H.sub.4 NHCOCH.sub.3 " "7-NHCOCH.sub.3 3-CONHC.sub.2 H.sub.5 C.sub.2 H.sub.4 CONH.sub.2 " "H 3-OCH.sub.3 C.sub.2 H.sub.4 NHCOCH.sub.3 " Na__________________________________________________________________________
TABLE 13__________________________________________________________________________ ##STR31##R.sup.2 R.sup.8 R.sup.4 X'Z M__________________________________________________________________________H H CH(CH.sub.3).sub.2 NHC.sub.2 H.sub.4 KH H " OC.sub.2 H.sub.4 K6-CH.sub.3 3-CH.sub.3 C.sub.2 H.sub.5 " Na" " C.sub.2 H.sub.4 OH " "" " C.sub.2 H.sub.4 SO.sub.2 NH.sub.2 NHC.sub.2 H.sub.4 Na" " " OC.sub.2 H.sub.4 K" " C.sub.2 H.sub.4 OCH.sub.3 NHC.sub.2 H.sub.4 K6-NHCOCH.sub.3 H C.sub.2 H.sub. 5 NHC.sub.3 H.sub.6 K" 3-CH.sub.3 " NHC.sub.2 H.sub.4 K" 3-CH(CH.sub.3).sub.2 C.sub.2 H.sub.4 OCH.sub.3 NHC.sub.2 H.sub.4 Na" " C.sub.2 H.sub.4 OSO.sub.3 K N(CH.sub.3)C.sub.2 H.sub.4 K" " C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 K" " C.sub.2 H.sub.4 OH N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 "6-NHCOOCH.sub.3 2-CH.sub.2 OH C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 Na6-NHSO.sub.2 CH.sub.3 " C.sub.2 H.sub.4 CN NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na5-OCH.sub.3, " C.sub.2 H.sub.4 OCOCH.sub.3 NHC.sub.2 H.sub.4 NH.sub.48-NHCOCH.sub.36-NHCOCH.sub.2 Cl 2-CH.sub.2 CH C.sub.6 H.sub.13 OC.sub.2 H.sub.4 K6-NHCOC.sub.2 H.sub.4 OH H C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 K5-CH.sub.3, 8-Cl 2-CH.sub.2 Cl CH.sub.2 C.sub.6 H.sub.5 NHC.sub.3 H.sub.6 K6-NHCONHC.sub.2 H.sub.5 2-CH.sub.2 Cl C.sub.2 H.sub.4 CN OC.sub.2 H.sub.4 NH.sub.46-NHCON(C.sub.2 H.sub.5).sub.2 2-CH.sub.2 OC.sub.6 H.sub.5 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 K6-CH.sub.3 " C.sub.2 H.sub.4 NHCOCH.sub.3 " "6-NHCOCH.sub.3 2-C.sub.2 H.sub.4 OC.sub.2 H.sub.5 C.sub.2 H.sub.4 CONH.sub.2 " "H " C.sub.2 H.sub.4 NHCOCH.sub.3 N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 Na__________________________________________________________________________
TABLE 14__________________________________________________________________________ ##STR32##R.sup.9 R.sup.2 R.sup.4 X'Z M__________________________________________________________________________C.sub.6 H.sub.5 H H NHC.sub.2 H.sub.4 Na" " CH.sub.3 " NaCH.sub.3 " C.sub.2 H.sub.4 OH NHC.sub.2 H.sub.4 NaCH.sub.3 " " OC.sub.2 H.sub.4 Na" 5-CH.sub.3 " NHC.sub.2 H.sub.4 KC.sub.6 H.sub.5 5-Cl H " "C.sub.6 H.sub.5 5-NHCOCH.sub.3 C.sub.2 H.sub.4 CN " "" 5-OCH.sub.3 CH.sub.3 " "" H " " Na" H " N(C.sub.2 H.sub.5)C.sub.2 H.sub.4 Na" H " N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 NaC.sub.6 H.sub.5 H C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 NaC.sub.6 H.sub.5 H CH.sub.3 NHC.sub.2 H.sub.4 NaCH.sub.3 6-CH.sub.3 CH.sub.3 " "CF.sub.3 " C.sub.6 H.sub.5 " "C.sub.6 H.sub.5 H C.sub.2 H.sub.5 " "C.sub.6 H.sub.5 H H " "CONH.sub.2 " CH.sub.3 " "CH.sub.3 " CH.sub.3 N(CH.sub.3)C.sub.2 H.sub.4 "Cl 5-OC.sub.2 H.sub.5 " NHC.sub.3 H.sub.6 "CH.sub.3 " H NHC.sub.2 H.sub.4 "C.sub.6 H.sub.4p-Br H H " "C.sub.6 H.sub.5 " C.sub.2 H.sub.4 CONH.sub.2 " KC.sub.6 H.sub.4p-OCH.sub.3 " C.sub.2 H.sub.4 CN N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 K" 6-C.sub.6 H.sub.11 C.sub.2 H.sub.4 SO.sub.2 NH.sub.2 NHC.sub.2 H.sub.4 "C.sub.2 H.sub.4 CN 4-OC.sub.6 H.sub.5 C.sub.2 H.sub.4 N(COCH.sub.3).sub.2 " "C.sub.2 H.sub.4 OCOCH.sub.3 5-SCH.sub.3 C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5 NHC.sub.2 H.sub.4 KCH.sub.3 5-SC.sub.6 H.sub.5 C.sub.2 H.sub.4 SO.sub.2 NH(C.sub.2 H.sub.5) NHCH.sub.2CH(C.sub.6 H.sub.5) K" 5-NHCOOCH.sub.3 C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 NaC.sub.3 H.sub.7 6-NHSO.sub.2 CH.sub.3 C.sub.2 H.sub.4 CN NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 NaCH.sub.3 6-OCH.sub.3, C.sub.2 H.sub.4 OCOCH.sub.3 NHC.sub.2 H.sub.4 NH.sub.4 5-NHCOCH.sub.3C.sub.2 H.sub.5 6-NHCOCH.sub.2 Cl C.sub.6 H.sub.13 OC.sub.2 H.sub.4 KOH 6-NHCOC.sub.2 H.sub.4 OH C.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 KSO.sub.2 NH.sub.2 " CH.sub.2 C.sub.6 H.sub.5 NHC.sub.3 H.sub.6 KSO.sub.2 NHC.sub.2 H.sub.5 6-NHCONHC.sub.2 H.sub.5 C.sub. 2 H.sub.4 CN OC.sub.2 H.sub.4 NH.sub.4OC.sub.6 H.sub.11 6-NHCON(C.sub.2 H.sub.5).sub.2 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 KSC.sub.2 H.sub.5 6-CH.sub.3 C.sub.2 H.sub.4 NHCOCH.sub.3 " "CONHC.sub.2 H.sub.5 6-NHCOCH.sub.3 C.sub.2 H.sub.4 CONH.sub.2 " "OCH.sub.3 H C.sub.2 H.sub.4 NHCOCH.sub.3 " NaNHOCC.sub.2 H.sub.5 " " " "C.sub.6 H.sub.4p-CH.sub.3 6-OH " " "__________________________________________________________________________
TABLE 15______________________________________ ##STR33##R.sup.9 R.sup.10 X'Z M______________________________________C.sub.6 H.sub.5 H NHC.sub.2 H.sub.4 Na" H NHCH[C(CH.sub.3).sub.3 ]CH.sub.2 Na" H OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na" CH.sub.3 " NaCH.sub.3 C.sub.6 H.sub.5 " Na" " OC.sub.2 H.sub.4 NaC.sub.6 H.sub.5 H NHC.sub.2 H.sub.4 KC.sub.6 H.sub.5 H NHC.sub.2 H.sub.4 Na" H " "" H " "" CH.sub.3 " "" H " "" " N(CH.sub.3)C.sub.2 H.sub.4 "" " N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 "C.sub.6 H.sub.5 H NHC.sub.2 H.sub.4 NaCH.sub.3 " OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 NaCH.sub.3 H OC.sub.2 H.sub.4 NaCH.sub.3 C.sub.6 H.sub.5 NHC.sub.2 H.sub.4 NaCH.sub.3 C.sub.6 H.sub.5 NHC.sub.3 H.sub.6 NaC.sub.6 H.sub.5 CH.sub.3 NHC.sub.2 H.sub.4 NaC.sub.6 H.sub.5 " " NH.sub.4" " N(C.sub.2 H.sub.5)C.sub.2 H.sub.4 "CH.sub.3 H NHC.sub.2 H.sub.4 K" H NH(CH.sub.2).sub.5 KC.sub.6 H.sub.4p-Br " OC.sub.2 H.sub.4 KC.sub.6 H.sub.4p-OCH.sub.3 " OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 K" Br NHC.sub.2 H.sub.4 KC.sub.2 H.sub.4 CN " N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 KC.sub.2 H.sub.4 OCOCH.sub.3 " NHC.sub.2 H.sub.4 KCONH.sub.2 C.sub.2 H.sub.5 NHCH.sub.2CH(C.sub.6 H.sub.5) KSCN C.sub.2 H.sub.5 OC.sub.2 H.sub.4 KSO.sub.2 C.sub.2 H.sub.5 C.sub.6 H.sub.5 NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 KOCOCH.sub.3 C.sub.6 H.sub.4p-CH.sub.3 NHC.sub.2 H.sub.4 KCONHC.sub.2 H.sub.5 " OC.sub.2 H.sub.4 KOH H OC.sub.2 H.sub.4 KSO.sub.2 NH.sub.2 CONHC.sub.2 H.sub.5 NHC.sub.3 H.sub.6 KSO.sub.2 NHC.sub.2 H.sub.5 CH.sub.3 OC.sub.2 H.sub.4 KOC.sub.6 H.sub.11 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 KC.sub.2 H.sub.5 SCN " KCONHC.sub.2 H.sub.5 CONH.sub.2 " KOCH.sub.3 CH(CH.sub.3).sub.2 " KNHOCC.sub.2 H.sub.5 C.sub.6 H.sub.5 " K" C.sub.2 H.sub.5 " K______________________________________
TABLE 16__________________________________________________________________________ ##STR34##R.sup.4 R.sup.11 X'Z M__________________________________________________________________________H CH.sub.3 NHC.sub.2 H.sub.4 KH C(CH.sub.3).sub.3 " "H CF.sub.3 " "H COOC.sub.2 H.sub.5 " "H CONHC.sub.2 H.sub.4 OSO.sub.3 Na " NaH C.sub.6 H.sub.5 " KC.sub.6 H.sub.5 CH.sub.3 " "" C(CH.sub.3).sub.3 " "" C.sub.6 H.sub.5 " Na" C.sub.6 H.sub.5 " "C.sub.6 H.sub.5 SO.sub.2 CH.sub.3 " "" " N(CH.sub.3)C.sub.2 H.sub.4 "" " N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 "H CH.sub.3 NHC.sub.2 H.sub.4 KH C.sub.6 H.sub.4p-OCH.sub.3 " "H CF.sub.3 " "H COOC.sub.2 H.sub.5 " " ##STR35## " NaH C.sub.6 H.sub.5 " KC.sub.6 H.sub.5 C.sub.6 H.sub.4p-Br " "" C(CH.sub.3).sub.3 " "" C.sub.6 H.sub.11 " Na" C.sub.6 H.sub.5 " NaC.sub.6 H.sub.5 SO.sub.2 CH.sub.3 N(CH.sub.3)C.sub.2 H.sub.4 NaC.sub.2 H.sub.5 SO.sub.2 " NHC.sub.2 H.sub.4 KCH.sub.3 CO " N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 KC.sub.6 H.sub.5 CO CH.sub.3 NHC.sub.2 H.sub.4 KCH.sub.3 CONH.sub.2 NHCH.sub.2CH(C.sub.6 H.sub.5) KC.sub.2 H.sub.4 OH C.sub.2 H.sub.5 OC.sub.2 H.sub.4 KC.sub.2 H.sub.4 CN " NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 KC.sub.2 H.sub.4 OCOCH.sub.3 " NHC.sub.2 H.sub.4 KC.sub.6 H.sub.11 CF.sub.3 OC.sub.2 H.sub.4 KC.sub.2 H.sub.4 OH C.sub.6 H.sub.4p-Cl OC.sub.2 H.sub.4 KCH.sub.2 C.sub.6 H.sub.5 CONHC.sub.2 H.sub. 5 NHC.sub.3 H.sub.6 KC.sub.2 H.sub.4 CN CH(CH.sub.3).sub.2 OC.sub.2 H.sub.4 KC.sub.2 H.sub.5 " NHC.sub.2 H.sub.4 KC.sub.2 H.sub.4 NHCOCH.sub.3 C.sub.2 H.sub.5 " KC.sub.2 H.sub.4 CONH.sub.2 CH.sub.3 " KC.sub.2 H.sub.4 NHCOCH.sub.3 C.sub.2 H.sub.5 " K" C.sub.6 H.sub.5 " K__________________________________________________________________________
TABLE 17__________________________________________________________________________ ##STR36##Q Q' R.sup.12 R.sup.13 X'Z M__________________________________________________________________________CO CO C.sub.6 H.sub.5 C.sub.6 H.sub.5 NHC.sub.2 H.sub.4 NaCO CO NH.sub.2 CH.sub. 3 " "CN CO -- NHCO.sub.2 C.sub.2 H.sub.5 OC.sub.2 H.sub.4 KCN CO -- CH.sub.2 OH NHC.sub.2 H.sub.4 NaCN CO -- CH.sub.3 OC.sub.2 H.sub.4 NaCO SO.sub.2 NH.sub.2 OC.sub.6 H.sub.5 NHC.sub.2 H.sub.4 NaCO SO.sub.2 CH.sub.2 Cl OCH.sub.3 NHC.sub.2 H.sub.4 NaCN SO.sub.2 -- C.sub.6 H.sub.5 NHC.sub.2 H.sub.4 NaCO CO CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 NHC.sub.2 H.sub.4 KCO CO 1,2-C.sub.6 H.sub.4 NHC.sub.2 H.sub.4 KCO CO C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NHC.sub.2 H.sub.4 KCO CO CH.sub.3 NH.sub.2 N(CH.sub.3)C.sub.2 H.sub.4 KCO CO NHC.sub.2 H.sub.5 NH.sub.2 N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 KCO CO NHC.sub.2 H.sub.5 CH.sub.3 OC.sub.2 H.sub.4 KCO SO.sub.2 NH.sub.2 C.sub.2 H.sub.5 OC.sub.2 H.sub.4 KCO CO SC.sub.2 H.sub.5 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 KCO CO SCH.sub.2C.sub.6 H.sub.5 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 KCO CO SC.sub.6 H.sub.11 OCH.sub.3 NHC.sub.2 H.sub.4 KCO CO C.sub.6 H.sub.5 OCH.sub.3 NHC.sub.2 H.sub.4 KCO CO NHCOC.sub.2 H.sub.5 NHCO.sub. 2 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 KCO CO NHSO.sub.2 C.sub.2 H.sub.5 NHCO.sub.2 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 KCO CO NHCOC.sub.6 H.sub.5 NHCO.sub.2 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 KCO CO OC.sub.2 H.sub.5 NHCO.sub.2 C.sub.2 H.sub.5 NHC.sub.2 H.sub.4 K__________________________________________________________________________
TABLE 18______________________________________ ##STR37##OHPosition R.sup.2 X'Z M______________________________________2 5-Cl NHC.sub.2 H.sub.4 Na2 5-Cl NHC(CH.sub.3).sub.2 CH.sub.2 Na2 5-OCH.sub.3 NHC(CH.sub.3).sub.2 CH.sub.2 Na3,4 H " K2 5-OCH.sub.3 " Na2 " NHC.sub.2 H.sub.4 "2 5-CH.sub.3 NHC.sub.2 H.sub.4 "3,4 H " "2 5-OCH.sub. 3 " K2 " " NH.sub.42 5-NHC.sub.6 H.sub.5 OC.sub.2 H.sub.4 Na2 " OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na2 5-NHCOCH.sub.3 NHC.sub.2 H.sub.4 Na2 5-NHCOCH.sub.3 OC.sub.2 H.sub.4 Na2 " OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na2 " N(CH.sub.3)C.sub. 2 H.sub.4 "2 " N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 "2 5-CH.sub. 3 NHC.sub.2 H.sub.4 Na2 " OC.sub.2 H.sub.4 Na2 5-OCH.sub.3 NHC.sub.2 H.sub.4 K2 5-Cl " Na2 5-Cl " Na4 2-OCH.sub.3 " K4 2-OCH.sub.3 " K3,4 H " Na3,4 H " Na2 3-NHCOCH.sub.3 " Na2 " N(CH.sub.3)C.sub.2 H.sub.4 K ##STR38## NHC.sub.2 H.sub.4 K C.sub.2 H.sub.4 OSO.sub.3 K2 5-C.sub.6 H.sub.11 NHC.sub.2 H.sub.4 "2 5-OC.sub.6 H.sub.5 N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 "2 5-SCH.sub.3 NHC.sub.2 H.sub.4 K2 5-SC.sub.6 H.sub.5 NHCH.sub.2CH(C.sub.6 H.sub.5) K2 5-NHCOOCH.sub.3 OC.sub.2 H.sub.4 Na2 5-NHSO.sub.2 CH.sub.3 NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na2 5-NCOCH.sub.3 NHC.sub.2 H.sub.4 NH.sub.42 5-NHCOCH.sub.2 Cl OC.sub.2 H.sub.4 K2 5-NHCOC.sub.2 H.sub.4 OH OC.sub.2 H.sub.4 K2 5-Cl NHC.sub.3 H.sub.6 K2 5-NHCONHC.sub.2 H.sub.5 OC.sub.2 H.sub.4 NH.sub.42 5-NHCON(C.sub.2 H.sub.5).sub.2 NHC.sub.2 H.sub.4 K2 5-CH.sub.3 " "2 5-NHCOCH.sub.3 " "4 H " Na______________________________________
TABLE 19__________________________________________________________________________ ##STR39##OHPosition R.sup.2 R.sup.14 X'Z M__________________________________________________________________________2 3-CO.sub.2 CH.sub.3 H OC.sub.2 H.sub.4 K4 H H " "4 H H " "4 H H NHC.sub.3 H.sub.6 OC.sub.2 H.sub.4 Na2 H H NHC.sub.2 H.sub.4 K2 3-CONH.sub.2 H " K2 3-CO.sub.2 CH.sub.3 H OC.sub.2 H.sub.4 Na2 H 6-SO.sub.2 N(CH.sub.3).sub.2 NHC.sub.2 H.sub.4 NHC.sub.2 H.sub.4 Na2 " 6-SO.sub.2 NHC.sub.3 H.sub.6 OCH.sub.3 OC.sub.2 H.sub.4 Na2 " 6-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 "2 " H NHC.sub.2 H.sub.4 "4 " " N(CH.sub.3)C.sub.2 H.sub.4 "2 " " N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 "2 3-CONH.sub.2 H NHC.sub.2 H.sub.4 K2 " " NHCH.sub.2CH(C.sub.6 H.sub.5) K2 3-CO.sub.2 CH.sub.3 " OC.sub.2 H.sub.4 Na2 " " NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 Na2 H " NHC.sub.2 H.sub.4 NH.sub.42 3-CO.sub.2 CH.sub.2 Cl " OC.sub.2 H.sub.4 K2 3-CO.sub.2 C.sub.2 H.sub.4 OH " OC.sub.2 H.sub.4 K4 H H NHC.sub.3 H.sub.6 K2 3-CONHC.sub.2 H.sub.5 " OC.sub.2 H.sub.4 NH.sub.42 3-CON(C.sub.2 H.sub.5).sub.2 " NHC.sub.2 H.sub.4 K2 3-CO.sub.2 C.sub.2 H.sub.5 " " "2 3-CO.sub.2 CH(CH.sub.3).sub.2 " " "2 H " N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 "__________________________________________________________________________
TABLE 20__________________________________________________________________________ ##STR40##R.sup.16 R.sup.17 R.sup.2 R.sup.14 X'Z M__________________________________________________________________________C.sub.6 H.sub.11 H H H OC.sub.2 H.sub.4 KC.sub.2 H.sub.4 CONH.sub.2 H H H " "C.sub.2 H.sub.4 SO.sub.2 CHCH.sub.2 H H 8-OH " "C.sub.2 H.sub.4 NHSO.sub.2 CH.sub.3 H H H NHC.sub.3 H.sub.6 OC.sub.2 H.sub.4 Na ##STR41## H 3-OCH.sub.3 8-OH NHC.sub.2 H.sub.4 KC.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub. 3 H H H " KCH(CH.sub.3)C.sub.2 H.sub.5 H H H OC.sub.2 H.sub.4 NaCH(CH.sub.3)CH.sub.2 CH(CH.sub.3)CH.sub.3 H H H NHC.sub.2 H.sub.4 NHC.sub.2 H.sub.4 NaC.sub.6 H.sub.5 C.sub.2 H.sub.4 OH 2-OCH.sub.3 H OC.sub.2 H.sub.4 NaC.sub.2 H.sub.5 H " H OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 "CH.sub.2 CH(OH)CH.sub.2 OH H " H NHC.sub.2 H.sub.4 "C.sub.2 H.sub.4 SO.sub.2 NH.sub.2 H " " N(CH.sub.3)C.sub.2 H.sub.4 "(CH.sub.2).sub.6 NHCOCH.sub.3 H " " N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 "C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH H H H NHC.sub.2 H.sub.4 KCH.sub.2 C.sub.6 H.sub.5 CH.sub.2 C.sub.6 H.sub.5 " " NHCH.sub.2CH(C.sub.6 H.sub.5) KCH.sub.3 H H " OC.sub.2 H.sub.4 NaC.sub.6 H.sub.11 H " " NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 NaC.sub.2 H.sub.4 CONH.sub.2 H H " NHC.sub.2 H.sub.4 NH.sub.4C.sub.2 H.sub.4 SO.sub.2 CHCH.sub.2 H H 8-OCH.sub.3 OC.sub.2 H.sub.4 K ##STR42## H 3-OC.sub.2 H.sub.5 8-OC.sub.2 H.sub.5 OC.sub.2 H.sub.4 K ##STR43## H H H NHC.sub.3 H.sub.6 KC.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3 CH.sub.3 H " OC.sub.2 H.sub.4 NH.sub.4CH(CH.sub.3)C.sub.2 H.sub.5 CH.sub.3 H " NHC.sub.2 H.sub.4 KCH(CH.sub.3)CH.sub.2 CH(CH.sub.3)CH.sub.3 CH.sub.3 3-C.sub.2 H.sub.5 " " "C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 H " " "C.sub.2 H.sub.5 " H " N(C.sub.6 H.sub.5)C.sub.2 H.sub.4 "__________________________________________________________________________
The invention has been described in detail with particular reference to certain preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope of the invention.

Number	Name	Date
2670265	Heyna et al.	Feb 1954
2773863	Bolliger	Dec 1956
2790172	Rudner	Apr 1957
3114754	Lodge et al.	Dec 1963
3232927	Randall et al.	Feb 1966
3531459	Chiddix et al.	Sep 1970
3957751	Bauer et al.	May 1976
3998805	Koller et al.	Dec 1976
4119623	Hugl et al.	Oct 1978

Azo dyes from 1,3,4-thiadiazol-2-yl and 1,2,4-thiadiazol-5-yl moieties bearing sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on their rings

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