Abstract:
Novel herbicidal compounds, compositions containing them, and methods for their use in controlling weeds are disclosed. The novel herbicidal compounds are represented by formula I:                            
     where J is a 1-substituted-6-trifluoromethyl-2,4-pyrimidinedione-3-yl, a 1-substituted-6-trifluoromethyl-1,3,5-triazine-2,4-dion-1-yl, a 3,4,5,6-tetrahydrophthalimid-1-yl, a 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl, a 5,6,7,8-tetrahydro-1H,3H-[1,3,4]thiadiazolo[3,5-a]pyridazineimin-1-yl, or a 1,6,8-triazabicyclo[4.3.0]-nonane-7,9-dion-8-yl ring attached at the 7 position of a benzofuran, benzoxazole, indole, 2,3-dihydrobenzimidazole or benzimidazole, and X is selected from hydrogen, halogen, cyano, nitro, and amino. Preferred R groups are optionally substituted alkyl groups.

Description:
This application is Divisional of Ser. No. 09/028,636 filed Feb. 24, 1998 now U.S. Pat. No. 6,077,812 which claims the benefit of Provisional Application No. 60/039,172 file Feb. 26, 1997. 
    
    
     BACKGROUND OF THE INVENTION 
     The present invention relates generally to novel herbicidal compounds and methods for their use in controlling unwanted plant species in agriculture. In particular, the present invention pertains to cycloimido-substituted benzofused heterocyclic herbicides, and more particularly it pertains to herbicides in which the benzofused heterocycle is a benzofuran, benzimidazole, a 2,3-dihydrobenzimidazole, or indole having a cycloimido moiety which is a 1 -substituted-6-trifluoromethyl-2,4-pyrimidinedione-3-yl, a 1-substituted-6-trifluoromethyl-1,3,5-triazine-2,4-dion-1-yl, a 3,4,5,6-tetrahydrophthalimid-1-yl, a 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl, a 5,6,7,8-tetrahydro-1H,3H-[1,3,4]thiadiazolo[3,5-a]pyridazineimin-1-yl, or a 1,6,8-triazabicyclo[4.3.0]-nonane-7,9-dion-8-yl ring. 
     SUMMARY OF THE INVENTION 
     It has now been found that certain cycloimido-substituted benzofused heterocyclic compounds are useful as pre-emergent and postemergent herbicides. These novel compounds are represented by formula I:                           
     where J is a 1-substituted-6-trifluoromethyl-2,4-pyrimidinedione-3-yl, a 1-substituted-6-trifluoromethyl-1,3,5-triazine-2,4-dion-1-yl, a 3,4,5,6-tetrahydrophthalimid-1-yl, a 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl, a 5,6,7,8-tetrahydro-1H,3H-[1,3,4]thiadiazolo[3,5-a]pyridazineimin-1-yl, or a 1,6,8-triazabicyclo[4.3.0]-nonane-7,9-dion-8-yl ring attached at the 7 position of a benzofuran, benzoxazole, 2,3-dihydrobenzimidazole, indole or benzimidazole, and X is selected from hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, and amino. Preferred R groups are optionally substituted alkyl groups. 
     DETAILED DESCRIPTION OF THE INVENTION 
     Certain cycloimido-substituted benzofused heterocyclic compounds have now been found to be useful as pre- and postemergent herbicides. These compounds are represented by formula I:                           
     where 
     (1) A is nitrogen double-bonded to position 2 and B is oxygen; 
     (2) A is oxygen and B is CR′ double bonded to position 2; 
     (3) A is NH and B is nitrogen double-bonded to position 2; 
     (4) A is nitrogen double bonded to position 2 and B is NR 2 ; 
     (5) A is CH double bonded to position 2 and B is NR 2 ; 
     (6) A is NH and B is CR′ double bonded to position 2; or 
     (7) A and B are NH 
     R is hydrogen, hydroxy, mercapto, straight or branched chain lower alkyl, cycloalkyl, alkoxy, aryl, heteroaryl, alkenyl, haloalkyl, hydroxyalkyl, haloaryl, alkoxyaryl, arylalkyl, aryloxyalkyl, haloarylalkyl, alkylthio, heterocyclyl, alkoxyalkyl, alkoxylalkyloxyalkyl, alkylcarbonyloxyalkyl, arylcarbonyloxyalkyl, aminocarbonyloxyalkyl, aminoalkyl, cyanoalkyl, aminoalkenyl, carboxy, carboxyalkyl, alkylcarboxy, alkylcarboxyalkyl, formyl, aminocarbonyl, amino, oxygen, cyano, nitro, alkylsulfonyl, aminosulfonyl, alkylsulfonylamino, alkoxycarbonyloxyalkyl, alkylcarboxylalkoxy, alkoxycarbonylamino, alkoxycarbonylalkylaminoalkyl, aryliminoalkyl, (aryl)(alkoxy)alkyl, (aryl)(alkylcarbonyloxy)alkyl, arylalkoxyalkyl, cyanoalkylthio, alkynylalkylthio, arylalkylthio, cyanothio, cyanothioalkyl, alkoxycarbonylalkylthio, aminocarbonylalkylthio, alkenylalkylthio, haloalkylalkynylalkylthio, aminocarbonyloxyalkyl, arylalkylcarbonylaminoalkyl, (hydroxy)(aryl)alkyl, alkylcarbonylaminoalkyl, alkylsulfonylaminoalkyl, aminocarbonylalkyl, alkoxycarbonyl, and alkenyloxy, where the amino group may be substituted with one or two substituents independently selected from alkyl, hydroxy, alkoxy, carboxy, aryl, alkylsufonyl, or haloalkylsulfonyl; 
     R 1  is hydrogen, lower alkyl, or haloalkyl; 
     R 2  is hydrogen, alkyl, haloalkyl, CO 2 (alkyl), CH 2 CO 2 (alkyl), CH 2 CONH-alkyl, CH 2 CON(alkyl) 2 , CH 2 CO 2 H, CH 2 OCH 3 , SO 2 (alkyl), CH 2 CH═CH 2 , CH 2 C≡CH. 
     X is selected from hydrogen, F, Cl, Br, alkyl, haloalkyl, CN, NO 2 , and NH 2 ; 
     n is 0-3; 
     J is selected from                           
     and 
     R 3 is selected from hydrogen, alkyl, haloalkyl, CH 2 CN, CH 2 CH═CH 2 , CH 2 C≡CH, CH 2 CO 2 (alkyl), CH 2 OCH 3 , and NH 2 . 
     Preferred compounds are those of formula I where R is CH 3 , CH 2 CH 3 , C(CH 3 ) 2 OH, CH 2 CH 2 OH, CH(CH 3 ) 2 , t-butyl, CF 3 , CH(F)CH 3 , CF 2 CF 3 , C(CH 3 ) 2 OCOCH 3 , C(CH 3 ) 2 NHSO 2 CH 3 , CH 2 CH 2 CH 2 C≡N CH 2 CH 2 CO 2 CH 3 , and CON(CH 3 ) 2 ; X is a chlorine, bromine or fluorine substituted in one or both of positions 4 and 6; J is                           
     and R 3  is CH 3  or NH 2 . 
     One aspect of the present invention relates to compounds of formula I in which A is nitrogen double-bonded to position 2 and B is oxygen, and R, R 3 , J, X and n are as described above. 
     Another aspect of the present invention relates to compounds of formula I in which A is oxygen and B is CR 1  double bonded to position 2, and R, R 1 , R 3 , J, X and n are as described above. 
     Another aspect of the present invention relates to compounds of formula I in which A is NH and B is nitrogen double-bonded to position 2, and R, J, X and n are as described above. 
     Another aspect of the present invention relates to compounds of formula I in which A is nitrogen double bonded to position 2 and B is NR 2 ,and R, R 2 , R 3 , J, X and n are as described above. 
     Another aspect of the present invention relates to compounds of formula I in which A is CH double bonded to position 2 and B is NR 2 , and R, R 2 , R 3 , J, X and n are as described above. 
     Another aspect of the present invention relates to compounds of formula I in which A is NH and B is CR 1  double bonded to position 2, and R, R 1 , R 3 , J, X and n are as described above. 
     Another aspect of the present invention relates to compounds of formula I in which A and B are NH and R, R 1 , R 3 , J, X and n are as described above. 
     Another aspect of the present invention relates to compounds of formula I where J is not                           
     when: A is oxygen and B is CR 1  double bonded to position 2; A is CH double bonded to position 2 and B is NR 2 ; or A is NH and B is CR 1  double bonded to position 2; and R, R 1 , R 3 , X, and n are as described above. 
     As shown in the specification a wide range of substituents is described for position B in compounds of formula I whereas position A is generally unsubstituted. It was found that some herbicidal activity is retained when a methyl substituent is placed at position A, but that substitution at that position generally causes a sharp decrease in activity. 
     Certain intermediates of the present invention are novel. These include compounds of formula II:                           
     where Y is NO 2 , NH 2 , or —NHN═C(CH 3 )R; Z is hydrogen, F, NH 2 , or OH; and R, J, X, and n are as described above; with the proviso that when Y is —NHN═C(CH 3 )R, Z is hydrogen. 
     As used in this specification and unless otherwise indicated, the terms “alkyl,” “alkenyl,” “alkynyl,” “h aloalkyl,” and “alkoxy” used alone or as part of a larger moiety, includes straight or branched carbon chains of 1 to 6 carbon atoms. “Halogen” refers to fluorine, bromine or chlorine. “THF” means tetrahydrofuran, “DMF” means N,N-dimethylformamide, and “DBU” means 1,8-diazabicyclo[5.4.0]undec-7-ene. When “n” in “X (n) ” is 2 or 3, the substituents X may be the same or different from one another.                           
     a) 70% HNO 3 / H 2 SO 4 , 0-5° C.; (b) NaOSi(CH 3 ) 3 , MeOH, dioxane; (c) Fe, EtOH, acetic acid, HCl, heat; (d) CF 3 C(NH 2 )═CO 2 CH 2 CH 5 , NaOSi(CH 3 ) 3 , DBU, DMF; (e) CH 3 I, K 2 CO 3 , DMF, 60-80° C.; (f) HCl, NaNO 2 , NaI, H 2 O; (g) BBr 3 , CH 2 Cl 2 ; (h) HC≡CR, Pd(Ph 3 P) 2 Cl 2 , Cul, triethylamine. 
     Benzofurans of formula I, where A is oxygen and B is CH double bonded to position 2, may be generally prepared as shown in Scheme 1. Starting with an appropriately substituted fluoroaniline derivative 1, nitration provides intermediate 2. Displacement of the fluorine of 2 with a methoxy group as shown in step b, followed by reduction of the nitro group as shown in step c provide the methoxyaniline 3. The methoxyaniline 3 is a versatile intermediate from which a number of compounds of the present invention can be made by attachment of various J groups. For example, a uracil ring may be appended as shown in step d to give intermediate 4a. At this point, R 3  substituents other than H may be introduced, as shown for example in step e to provide 4b where R 3  is methyl. Using diazotization conditions (step f) 4b is converted to the iodoanisole 5 which is then deprotected to give the iodophenol 6. Palladium-catalyzed acetylenic coupling and ring closure as shown in step h give benzofurans 7 of the present invention. To obtain benzofurans of formula I where the J group is other than uracil, approaches analogous to that outlined in Scheme 1 may be followed. Such approaches based on Scheme 1 would be known to one skilled in the art.                           
     a) 70% HNO 3 /H 2 SO 4 , 0-5° C.; (b) Fe, aqueous acetic acid, 50° C.; (c) RCOCl, pyridinium p-toluenesulfonate, triethylamine, xylene; (d) 1,1-carbonylimidazole, THF; (e) R′-halide, Ag 2 O, CH 2 Cl 2  (to give 11 where R═R′O). 
     Benzoxazoles of formula I, where A is nitrogen double bonded to position 2 and B is oxygen, may be prepared as shown in Scheme 2 above. Starting with a phenol such as intermediate 8 nitration under standard conditions gives the nitrophenol 9. Certain of the benzoxazoles 11 of the present invention may be obtained by reduction of 9 to the aniline 10 followed by treatment with an acid halide (such as shown in step c). Alternatively, other benzoxazoles 11 may be obtained by treating 10 with carbonyldiimidazole to give intermediate 12 which can be O-alkyated according to step e. The approach outlined in Scheme 2 can be adapted, in ways known to one skilled in the art, to obtain benzoxazoles of formula I where the J group is other than uracil.                           
     a) see steps (d) and (e) of Scheme 1; (b) 70% HNO 3 /H 2 SO 4 , 0-5° C.; (c) NH 4 OAc, triethylamine, dioxane, heat; (d) SnCl 2  H 2 O or Fe, NH 4 Cl, aqueous ethanol, heat; (e) RCO 2 H, heat; RCO-halide, CH 2 Cl 2 /Pyridine, then POCl 3 , CH 2 Cl 2 ; alkoxycarbonyl isothiocyanate, HgCl 2 , heat (where R is —NHCO 2 alkyl); or thiophosgene, EtOAC, heat (where R is —SH). 
     Benzimidazoles of formula I, where A is NH and B is nitrogen double bonded to position 2, may be prepared as shown in Scheme 3 above. For example, intermediate 13 may be converted to the uracil 14 by the well-known chemistry previously described. Nitration of 14 followed by aminolysis of the fluorine group (steps b and c) provides the nitroaniline 15. The diamine 16 is obtained by reduction of 15 under standard conditions. Benzimidazoles 17 of the present invention are obtained by treatment of 16 with a carboxylic acid, an acid halide, an alkoxycarbonyl isothiocyanate, or thiophosgene according to step e. Other benzimidazoles 17 of the present invention are obtained by derivativization of benzimidazoles depicted in Scheme 3 using techniques known to one skilled in the art. The approach outlined in Scheme 3 can be adapted, in ways known also to one skilled in the art, to obtain benzimidazoles of formula I where the J group is other than uracil.                           
     Benzimidazoles of structure 17A where R 3  is NH 2  are prepared in a manner analogous to that depicted in Scheme 3, except the NH 2  group is attached following nitration of the phenyl ring. The 1-unsubstituted uracil ring is formed as previously described in step d of Scheme 1, followed by nitration of the phenyl ring (Scheme 3, step b). The uracil ring is then aminated in the 1-position by methods known in the art by treating it with 1-aminooxysulfonyl-2,4,6-trimethylbenzene. The 1-aminouracil is then subjected to aminolysis of the phenyl fluorine (step c) followed by reduction to the diamine (step d).                           
     2,3-Benzimidazoles of formula I, where A and B are NH may be prepared from Intermediate 16 in Scheme 3 by heating it with an appropriately substituted acetaldehyde ethyl hemiacetal, affording compounds of Structure 17B.                           
     a) i. NaNO 2 , HCl; ii. SnCl 2′ 2H 2 O; iii. RCOCH 3 ; (b) polyphosphoric acid, 80° C. 
     Indoles of formula I, where A is CH double bonded to position 2 and B is NR 1 , may be prepared according to Scheme 4 above. Using a Fischer indole route the starting aniline 18 may be converted to the corresponding hydrazone 19 which in turn may be cyclized under acidic conditions such as is shown in step b. The resulting indoles 20 of the present invention may be further derivatized by alkylation of the indole ring nitrogen to indoles of formula I where R 1  is other than hydrogen. The approach outlined in Scheme 4 can be adapted, in ways known to one skilled in the art, to obtain indoles of formula I where the J group is other than uracil.                           
     Indoles of formula I, where A is NH and B is CR 1  double bonded to position 2, may be prepared by a Fischer indole synthesis analogous to that shown in Scheme 4 starting with aniline 21. Substitution at the 3 position of indoles such as 22 with R 1  groups is known to one skilled in the art. 
    
    
     Compounds of the present invention may also be prepared in accordance with the procedures shown in the Examples below, by procedures analogous to those shown in the Examples, or by other methods that are generally known or available to one skilled in the art. 
     EXAMPLE 1 
     1-METHYL-6-TRIFLUOROMETHYL-3-[7-BROMO-5-FLUORO-2-(2-METHYLCARBONYLOXYPROP-2-YL)BENZOXAZOL-4-YL]-2,4(1 H,3H)-PYRIMIDINEDIONE (COMPOUND 104) 
     Step A 1-methyl-6-trifluoromethyl-3-(4-bromo-2-fluoro-5-hydroxy-6-nitrophenyl)-2,4(1H,3H)-pyrimidinedione 
     A stirred solution of 17.0 grams (0.044 mole) of 1-methyl-6-trifluoromethyl-3-(4-bromo-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione and 5.0 grams (0.050 mole) of sulfuric acid in 100 mL of glacial acetic acid was cooled to 15° C., and 3.2 grams (0.050 mole) of 70% nitric acid was added dropwise. The reaction mixture was then allowed to warm to ambient temperature where it stirred for two hours. The reaction mixture was poured into water and extracted with diethyl ether. The extract was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel, yielding 16.4 grams of title compound; mp 76-78° C. 
     Step B 1-methyl-6-trifluoromethyl-3-(6-amino-4-bromo-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione 
     A stirred solution of 16.0 grams (0.037 mole) of 1-methyl-6-trifluoromethyl-3-(4-bromo-2-fluoro-5-hydroxy-6-nitrophenyl)-2,4(1H,3H)-pyrimidinedione and 10 mL of water in 120 mL of glacial acetic acid was heated to 50° C., and 16.0 grams (excess) of iron dust was slowly added. The reaction mixture was then cooled to ambient temperature where it stirred for one hour. The reaction mixture was filtered through diatomaceous earth, and the filtrate was partitioned in a mixture of 150 mL portions each of water and ethyl acetate. The organic layer was separated, dried with magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel, yielding 12.0 grams of title compound; mp 98-100° C. 
     Step C Compound 104 
     A stirred solution of 0.50 gram (0.0013 mole) of 1-methyl-6-trifluoromethyl-3-(6-amino4-bromo-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione, 0.21 gram (0.0013 mole) of 1-chlorocarbonyl-1-methylethyl acetate, 0.14 gram (0.0014 mole) of triethylamine, and 0.16 gram (0.0006 mole) of pyridinium p-toluenesulfonate in 50 mL of xylene was heated at 150° C. for about 18 hours. The reaction mixture was then cooled to ambient temperature and taken up in ethyl acetate. The solution was washed with water and an aqueous solution saturated with sodium chloride; then it was dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel, yielding 0.72 gram of Compound 104. The NMR spectrum was consistent with the proposed structure. 
     EXAMPLE 2 
     1-METHYL-6-TRIFLUOROMETHYL-3-(7-BROMO-5-FLUORO-2-METHOXYBENZOXAZOL-4-YL)-2,4(1H,3H)-PYRIMIDINEDIONE (COMPOUND 109) 
     Step A 1-methyl-6-trifluoromethyl-3-(7-bromo-5-fluorobenzoxazol-2-on4-yl)-2,4(1H,3H)-pyrimidinedione 
     A stirred solution of 2.0 grams (0.005 mole) of 1-methyl-6-trifluoromethyl-3-(6-amino-4-bromo-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione and 1.2 grams (0.008 mole) of carbonylimidazole in 50 mL of THF was heated at reflux for three hours. The reaction mixture was cooled and concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel, yielding 1.1 grams of title compound. The NMR spectrum was consistent with the proposed structure. 
     Step B Compound 109 
     A mixture of 0.50 gram (0.001 mole) of 1-methyl-6-trifluoromethyl-3-(7-bromo-5-fluorobenzoxazol-2-on-4-yl)-2,4(1H,3H)-pyrimidinedione 0.17 gram (0.001 mole) of methyl iodode, and 0.27 gram (0.001 mole) of silver(I) oxide in 50 mL of methylene chloride was stirred at ambient temperature for two hours. The product was isolated from the reaction mixture by column chromatography on silica gel, yielding 0.28 gram of Compound 109. The NMR spectrum was consistent with the proposed structure. 
     EXAMPLE 3 
     1-METHYL-6-TRIFLUOROMETHYL-3-[7-CHLORO-5-FLUORO-2-(1-METHYLETHYL)BENZOXAZOL4-YL]-2,4(1H,3H)-PYRIMIDINEDIONE (COMPOUND 28) 
     Step A 1-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione 
     A stirred solution of 18.2 grams (0.054 mole) of 1-methyl-6-trifluoromethyl-3-(5-amino4-chloro-2-fluorophenyl)-2,4(1H,3H)-pyrimidinedione in 100 mL of sulfuric acid was cooled to 5° C., and a solution of 3.7 grams (0.054 mole) of sodium nitrite in about 10 mL of water was added dropwise. The reaction mixture was then warmed to ambient temperature where it stirred for two hours. In a separate reaction vessel, a stirred mixture of 242 grams (0.970 mole) of copper(II) sulfate and 1.5 grams (0.005 mole) of iron(II) sulfate heptahydrate in about 300 mL of water and 300 mL of xylene was heated to reflux, and the pyrimidinedione diazonium solution prepared above was added dropwise. The reaction mixture was stirred at reflux for two additional hours, then allowed to cool as it stirred for about 18 hours. The reaction mixture was poured into about 600 mL of water, and the aqueous/organic layers were separated. The aqueous layer was washed with ethyl acetate, and the wash was combined with the organic layer. The combined organic material was washed with water, then with an aqueous solution saturated with sodium chloride. The organic material was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding impure product. The product was dissolved in diethyl ether and washed with aqueous 10% hydrochloric acid, and with water. The diethyl ether solution was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 7.6 grams of title compound. The NMR spectrum was consistent with the proposed structure. 
     Step B 1-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxy-6-nitrophenyl)-2,4(1H,3H)-pyrimidinedione 
     This compound was prepared in the manner of Step A of Example 1, using 3.8 grams (0.011 mole) of 1-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione, 1.0 gram (0.011 mole) of 70% nitric acid, and 50 mL of sulfuric acid, yielding 1.5 grams of title compound. The NMR spectrum was consistent with the proposed structure. 
     Step C 1-methyl-6-trifluoromethyl-3-(6-amino4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione 
     This compound was prepared in the manner of Step B of Example 1, using 1.5 grams (0.004 mole) 1-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxy-6-nitrophenyl)-2,4(1H,3H)-pyrimidinedione, 3.0 grams (0.054 mole) of iron dust, and 5 mL of water in 50 mL of glacial acetic acid, yielding 1.0 gram of title compound. The NMR spectrum was consistent with the proposed structure. 
     Step D Compound 28 
     This compound was prepared in the manner of Step C of Example 1, using 0.52 gram (0.0015 mole) of 1-methyl-6-trifluoromethyl-3-(6-amino4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione, 0.18 gram (0.0017 mole) of isobutyryl chloride, 0.24 gram (0.0017 mole) of triethylamine, and 0.09 gram (0.0004 mole) of pyridinium p-toluenesulfonate in 50 mL of xylene, yielding 0.22 gram of Compound 28. The NMR spectrum was consistent with the proposed structure. 
     EXAMPLE 4 
     SYNTHESIS OF 3-(4-CHLORO-6-FLUORO-2-PHENYLBENZOFURAN-7-YL)-1-METHYL-6-TRIFLUOROMETHYL-2,4(1H,3H)-PYRIMIDINEDIONE 
     (COMPOUND 280) 
     Step A ethyl N-(4-chloro-2,6-difluoro-3-nitrophenyl)carbamate 
     A stirred solution of 23.6 grams (0.109 mole) of ethyl N-(4-chloro-2,6-difluorophenyl)carbamate in 125 mL of concentrated sulfuric acid was cooled to about 0° C. and 7.7 mL (0.123 mole) of 70% nitric acid was added dropwise at a rate to maintain the reaction temperature below 10° C. Upon completion of addition, the reaction mixture was stirred at 10° C. for 30 minutes and then allowed to warm to ambient temperature where it stirred for about 18 hours. At the conclusion of this period, the reaction mixture was poured into 150 mL of ice-water. The resulting precipitate was collected by vacuum filtration and washed with water followed by petroleum ether. The precipitate was dried in a heated vacuum desicator, yielding 30.6 grams of title compound. The NMR spectrum was consistent with the proposed structure. 
     Step B ethyl N-(4-chloro-6-fluoro-2-methoxy-3-nitrophenyl)carbamate 
     Under a nitrogen atmosphere, a solution of 30.6 grams (0.109 mole) of ethyl N-(4-chloro-2,6-difluoro-3-nitrophenyl)carbamate and 18 mL (0.449 mole) of methanol in 175 mL of dioxane was stirred and 218 mL (0.218 mole) of 1M sodium trimethylsilanoate (in tetrahydrofuran) was added dropwise during a 45 minute period. Upon completion of addition, the reaction mixture was heated to 65° C. where it stirred for three hours. At the conclusion of this period, the reaction mixture was allowed to cool to ambient temperature where it stirred for about 18 hours. The reaction mixture was concentrated under reduced pressure to a residue. The residue was taken up in cold 3N hydrochloric acid. The resulting solid was collected by filtration, washed with petroleum ether, and heat dried under vacuum, yielding 21.3 grams of title compound. The NMR spectrum was consistent with the proposed structure. 
     Step C ethyl N-(3-amino-4-chloro-6-fluoro-2-methoxyphenyl)-carbamate 
     Under a nitrogen atmosphere, a stirred solution of 21.3 grams (0.072 mole) of ethyl N-(4-chloro-6-fluoro-2-methoxy-3-nitrophenyl)-carbamate, 18.3 grams (0.328 mole) of iron powder, 50 mL of acetic acid, and 250 mL of ethanol was heated to 65° C. where it stirred for two hours. At the conclusion of this time, 3 mL (0.036 mole) of 12M hydrochloric acid was added. Upon completion of addition, the reaction mixture was stirred for an additional two hours. After this time, the reaction mixture was concentrated under reduced pressure to yield a brown oil. The oil was then taken up in methylene chloride. The mixture was filtered through diatomaceous earth, and the filter cake was washed with water and an aqueous saturated sodium bicarbonate solution. The filtrate was stored over sodium sulfate for about 18 hours and then filtered. The solvent was removed under reduced pressure to yield a black oil. This oil was filtered through a silica gel pad, yielding 15.0 grams of ethyl N-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)carbamate. The NMR spectrum was consistent with the proposed structure. 
     Step D 3-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione 
     This compound was prepared using 4.0 grams (0.036 mole) of sodium trimethylsilanolate, 6.6 grams (0.036 mole) of ethyl 3-amino4,4,4-trifluorocrotonate, 8.5 grams (0.032 mole) of ethyl N-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)carbamate, and 2.2 grams (0.014 mole) of DBU in 75 mL of DMF. This preparation differs from well-known literature preparations for pyrimidinedione rings in that sodium trimethylsilanolate and DBU were used rather than sodium hydride. The yield of title compound was 1.7 grams. The NMR spectrum was consistent with the proposed structure. 
     Step E 3-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione 
     A solution of 7.5 grams (0.021 mole) of 3-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione, 3.4 grams (0.025 mole) of potassium carbonate, and 3.5 grams (0.025 mole) of methyl iodide in 200 mL of acetone was stirred at ambient temperature for about 18 hours. The reaction mixture was then concentrated under reduced pressure, and the residue was taken up in 200 mL of water. The mixture was extracted with two 100 mL portions of ethyl acetate. The combined extracts were washed with two 50 mL portions of an aqueous saturated sodium chloride solution. The organic layer was dried with magnesium sulfate, filtered, and concentrated under reduced pressure, yielding 6.9 grams of crude product. The dark oil was combined with 7.0 grams of crude product prepared by a similar route to yield a total of 13.9 grams of crude product. The crude product was purified by column chromatography on silica gel, yielding 10.0 grams of title compound. The NMR spectrum was consistent with the proposed structure. 
     Step F 3-(4-chloro-6-fluoro-3-iodo-2-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione 
     A solution of 4.0 grams (0.011 mole) of 3-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione in 25 mL (0.300 mole) of concentrated hydrochloric acid was stirred and cooled in an ice bath. During a 15 minute period, 1.9 grams (0.013 mole) of sodium nitrite was added dropwise at a rate to maintain the reaction temperature at 15° C. Upon completion of addition, the mixture was stirred for 20 minutes and then poured into 15.0 grams (0.090 mole) of potassium iodide. The reaction mixture was stirred for 30 minutes and then filtered. The filter cake was thoroughly washed with distilled water and then taken up in 150 mL of ethyl acetate. The resulting solution was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield a brown solid. The solid was subjected to column chromatography on silica gel. Elution was accomplished using 5:1 heptane and ethyl acetate. The product-containing fractions were combined and concentrated under reduced pressure, yielding 3.0 grams of title compound. The NMR spectrum was consistent with the proposed structure. 
     Step G 3-(4-chloro-6-fluoro-2-hydroxy-3-iodophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione 
     Under a nitrogen atmosphere, a stirred solution of 3.0 grams (0.006 mole) of 3-(4-chloro-6-fluoro-3-iodo-2-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione in 75 mL of methylene chloride was cooled in a dry ice/acetone bath and 22.0 mL (0.022 mole) of 1M boron tribromide (in methylene chloride) was added dropwise during a 20 minute period. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature were it stirred for about one hour. At the conclusion of this period, the reaction mixture was poured into 200 mL of water and extracted with two 50 mL portions of methylene chloride. The combined extracts were washed with one 100 mL portion of an aqueous saturated sodium chloride solution, dried with sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, yielding 2.6 grams of title compound. The NMR spectrum was consistent with the proposed structure. 
     Step H Compound 280 
     Under a nitrogen atmosphere, a solution of 1.5 grams (0.003 mole) of 3-(4-chloro-6-fluoro-2-hydroxy-3-iodophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, 0.41 gram (0.004 mole) of phenylacetylene, and 0.71 gram (0.007 mole) of triethylamine in 25 mL of DMF was stirred. To this was added 0.09 gram (0.00013 mole) of dichlorobis(triphenylphosphine)pallidium (II) and 0.05 gram (0.00026 mole) of copper (I) iodide. Upon completion of addition, the reaction mixture was heated to 70° C. where it stirred for 2.5 hours. After this time, the reaction mixture was cooled to ambient temperature and then poured into 150 mL of an aqueous 10% ammonium chloride solution. The resulting precipitate was collected by filtration and washed with water. The precipitate was taken up in 120 mL of ethyl acetate. The resulting solution was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a brown solid. The solid was recrystallized using 1:1 chloroform and petroleum ether, yielding 0.31 gram of Compound 280. The mother liquor was concentrated to a residue. The residue was recrystallized using petroleum ether to yield an additional 0.21 gram of Compound 280, m.p. 215-216° C. The NMR spectrum was consistent with the proposed structure. 
     EXAMPLE 5 
     SYNTHESIS OF 3-(4-CHLORO-6-FLUORO-2-TRIFLUOROMETHYLBENZIMIDAZOL-7-YL)-1-METHYL-6-TRIFLUOROMETHYL-2,4(1H,3H)-PYRIMIDINEDIONE (COMPOUND 365) 
     A stirred solution of 3.0 grams (0.0085 mole) of 3-(5,6-diamino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione in 15.0 mL of trifluoroacetic acid was heated to 65° C. where it stirred for one hour. At the conclusion of this period, the reaction mixture was analyzed by TLC, which indicated that the reaction was not complete. The reaction mixture was stirred at 65° C. for an additional two hours. After this time, the reaction mixture was again analyzed by TLC, which indicated that the reaction was complete. The reaction mixture was allowed to cool to ambient temperature and then poured into 200 mL of water. The resulting mixture was allowed to stand at ambient temperature for about 18 hours. At the conclusion of this period, the resulting solid was collected by filtration and washed with water followed by heptane. The filter cake was dried under vacuum, yielding 3.6 grams of Compound 365, m.p. 130° C. The NMR spectrum was consistent with the proposed structure. 
     EXAMPLE 6 
     SYNTHESIS OF 3-(4-CHLORO-2-ETHYL-6-FLUOROBENZIMIDAZOL-7-YL)-1-METHYL-6-TRIFLUOROMETHYL-2,4(1H,3H)-PYRIMIDINEDIONE (COMPOUND 367) 
     Step A 3-(4-chloro-2,6-difluorophenyl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione 
     Under a nitrogen atmosphere, a solution of 32.0 grams (0.900 mole) of sodium hydride (60% by weight) in 250 mL of DMF was vigorously stirred and cooled in an ice bath. To this a solution of 133.0 grams (0.726 mole) of ethyl 3-amino-4,4,4-trifluorocrotonate in 150 mL of DMF was added dropwise at a rate to maintain the reaction mixture temperature at about 5° C. Upon completion of addition, a solution of 156.3 grams (0.663 mole) of ethyl N-(4-chloro-2,6-difluorophenyl)carbamate in 250 mL of DMF was added dropwise. Upon completion of addition, the mixture was removed from the ice bath and heated to 130° C. where it stirred for 3.5 hours. After this time, the mixture was analyzed by gas chromatography (GC), which indicated that only a slight amount of the starting material was left. The mixture was cooled to 5° C. and 83.0 mL (1.333 moles) of methyl iodide was added dropwise at a rate to maintain the reaction mixture temperature below 20° C. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature where it stirred for about 18 hours. At the conclusion of this period, the reaction mixture was filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure to yield a dark viscous oil. The oil was taken up in methylene chloride and washed with three 1000 mL portions of water followed by one 1000 mL portion of an aqueous saturated sodium chloride solution. The organic layer was dried with magnesium sulfate, filtered, and concentrated under reduced pressure, yielding 223.8 grams of title compound. The NMR spectrum was consistent with the proposed structure. 
     Step B 3-(4-chloro-2,6-difluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione 
     A stirred solution of 211.0 grams (0.619 mole) of 3-(4-chloro-2,6-difluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione in 600 mL of concentrated sulfuric acid was cooled to less than 10° C., and 44 mL (0.689 mole) of aqueous 70% nitric acid was added dropwise at a rate to maintain the reaction temperature below 10° C. Upon completion of addition, the reaction mixture was analyzed by GC, which indicated the reaction was incomplete. The reaction was allowed to warm to ambient temperature and an additional 5 mL (0.078 mole) of aqueous 70% nitric acid was added. The reaction mixture was again analyzed by GC, which indicated the reaction was complete. The reaction mixture was poured into ice-water. The resulting solid was collected by filtration, washed with water, and then taken up in 600 mL of methylene chloride. The resulting solution was washed with two 600 mL portions of water, one 600 mL portion of an aqueous saturated sodium bicarbonate solution, and one 600 mL portion of an aqueous saturated sodium chloride solution. The organic layer was separated, dried with magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, yielding a waxy tan solid. The solid was triturated with heptane and allowed to stand for about 72 hours. At the conclusion of this period, the solid was collected by filtration, washed with heptane, and dried under reduced pressure, yielding 201.4 grams of title compound. The NMR spectrum was consistent with the proposed structure. 
     Step C 3-(6-amino4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione 
     To stirred solution of 200 grams (0.519 mole) of 3-(4-chloro-2,6-difluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione in 1000 mL of dioxane was added 150 mL (1.091 moles) of triethylamine in one portion. Upon completion of addition, the mixture was vigorously stirred and 400 grams (5.189 moles) of ammonium acetate was added in one portion. The reaction mixture was heated to 90° C. where it stirred for two hours. The reaction mixture was allowed to cool to ambient temperature where it stirred for about 18 hours. The resulting suspension was collected by filtration and washed with dioxane. The filtrate was concentrated under reduced pressure to yield a viscous dark oil. The oil was poured into ice-water. The resulting solid was collected by filtration and washed with water. The solid was dried under reduced pressure and then at ambient temperature for about 18 hours, yielding 195.1 grams of title compound. The NMR spectrum was consistent with the proposed structure. 
     Step D 3-(5,6-diamino4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione and 3-(5,6-diamino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione 
     A solution of 278.0 grams (1.232. moles) of tin(II) chloride dihydrate, 264.0 grams (4.936 moles) of ammonium chloride, 400 mL of water, and 800 mL of ethanol was vigorously stirred, and 157.4 grams (0.411 mole) of 3-(6-amino4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione was added. Upon completion of addition, the reaction mixture was heated to 83-85° C. where it stirred for 18 hours. After this time the reaction mixture was allowed to cool to ambient temperature. The resultant solid by-product was collected by filtration and washed with ethanol. The combined filtrate and wash was concentrated under reduced pressure to yield a suspension of additional by-product. The suspension was taken up in ethyl acetate and the resultant emulsion was filtered through a pad of diatomaceous earth. The filter cake was washed with ethyl acetate, and the combined organics were washed with three 200 mL portions of water. The organic layer was dried with magnesium sulfate, filtered, and concentrated under reduced pressure to a brown residue. The residue was triturated with heptane and allowed to stand for about five days. The resultant solid was collected by filtration and dried, yielding 144.4 grams of crude product. The crude product was combined with material prepared by a similar route, yielding a total of 157.8 grams of material. The combined product was subjected to column chromatography on silica gel, yielding 83.2 grams of an orange solid. The solid was slurried with warm ethyl acetate, and the insoluble product was collected by filtration. The product was washed with ethyl acetate, and the wash and filtrate from above were combined. The process of concentrating the filtrate, and slurrying the solid residue was repeated twice more, yielding a total of 51.9 grams of title compound. The NMR spectrum was consistent with the proposed structure. 
     An alternate method for preparing 3-(5,6-diamino4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione is the following: 
     A solution of 19.2 grams (0.050 mole) of 3-(6-amino4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, 3.0 grams (0.056 mole) of ammonium chloride, and 50 mL of water in 100 mL of ethanol was stirred, and 11.2 grams (0.201 mole) of iron powder (325 mesh) was added in one portion. Upon completion of addition, the reaction mixture was heated at reflux for one hour. The reaction mixture was allowed to cool to ambient temperature, then it was filtered through diatomaceous earth to remove the iron powder. The filter cake was washed with 200 mL of acetone, and the wash was combined with the filtrate. The combination was stirred with decolorizing carbon and filtered. The filtrate was concentrated under reduced pressure, yielding a dark brown oil. The oil was then taken up in 200 mL of methylene chloride and washed with three 100 mL portions of an aqueous saturated sodium bicarbonate solution. The organic layer was dried with magnesium sulfate, filtered, and concentrated under reduced pressure, yielding 12.8 grams of title compound. The NMR spectrum was consistent with the proposed structure. 
     Step E Compound 367 
     A stirred solution of 1.0 grams (0.0028 mole) of 3-(5,6-diamino4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione and 0.28 mL (0.0035 mole) of pyridine in 10 mL chloroform was cooled to 5° C. and 0.27 mL (0.0031 mole) of propionyl chloride was added dropwise. Upon completion of addition, the mixture was allowed to warm to ambient temperature were it stirred for about 18 hours. The mixture was cooled to 5° C. and 5.0 mL (0.054 mole) of phosphorous oxychloride was added in one portion. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature where it stirred for about 18 hours. At the conclusion of this period, the reaction mixture was poured into 200 mL of cold water, the resulting mixture was stirred for one hour, then it was extracted with three 50 mL portions of chloroform. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 0.15 gram of an orange residue. The aqueous layer was made basic with an aqueous saturated sodium bicarbonate solution to a pH of 34. The resulting mixture was extracted with three 50 mL portions of methylene chloride. The extracts were combined, dried with magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, yielding 0.70 gram of a yellow residue. The yellow residue was triturated with hot heptane. The resulting solid was collected by filtration and washed with heptane, yielding 0.67 gram of Compound 367, m.p. 150-155° C. The NMR spectrum was consistent with the proposed structure. 
     EXAMPLE 7 
     SYNTHESIS OF 3-(2-T-BUTYL4-CHLORO-6-FLUOROBENZIMIDAZOL-7-YL)-1-METHYL-6-TRIFLUOROMETHYL-2,4(1H,3H)-PYRIMIDINEDIONE (COMPOUND 369) 
     To a stirred solution of 1.0 grams (0.0028 mole) of 3-(5,6-diamino4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione , 15.0 mL of ethanol, and 4 mL of 5M hydrochloric acid was added 1.2 mL (0.0057 mole) of 2,2,6,6-tetramethyl-3,5-heptanedione. Upon completion of addition, the reaction mixture was heated to reflux where it stirred for ten minutes. At the conclusion of this period, the reaction mixture was analyzed by TLC, which indicated that the reaction was not complete. The reaction mixture was stirred at reflux for an additional two hours. After this time, the reaction mixture was again analyzed by TLC, which again indicated that the reaction was still not complete. As a result, an additional 1.0 mL (0.0048 mole) of 2,2,6,6-tetramethyl-3,5-heptanedione was added. Upon completion of addition, the reaction mixture was stirred at reflux for three days. At the conclusion of this period, more ethanol was added to replace that which evaporated, and the reaction mixture was analyzed by TLC for a third time. The reaction mixture was allowed to cool to ambient temperature, poured into 100 mL of an aqueous saturated sodium bicarbonate solution, and 100 mL of chloroform was added. The aqueous layer was separated and washed with two 100 mL portions of chloroform. The chloroform layer and washes were combined, dried with magnesium sulfate, and filtered. The filtrate was treated with decolorizing carbon and stirred. The mixture was filtered and concentrated under reduced pressure to yield a red oil. The oil was taken up in heptane. The resulting solid was collected by filtration and washed with heptane to yield a tan solid. The solid was purified by column chromatography on silica gel, yielding 0.36 gram of Compound 369, m.p. 125-130° C. The NMR spectrum was consistent with the proposed structure. 
     EXAMPLE 8 
     SYNTHESIS OF 3-(7-CHLORO-5-FLUORO-2-TRIFLUOROMETHYLINDOL-4-YL)-1-METHYL-6-TRIFLUOROMETHYL-2,4(1H,3H)-PYRIMIDINEDIONE (COMPOUND 500) 
     Step A 3-[5-(1-trifluoromethylethylidenehydrazino)4-chloro-2-fluorophenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione 
     A solution of 3.37 grams (0.010 mole) of 3-(5-amino4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione in 80 mL of concentrated hydrochloric acid was stirred at 25° C. for 20 minutes. After this time, the solution was cooled to 10° C. and a solution of 0.69 gram (0.010 mole) of sodium nitrite in 10 mL of water was slowly added. Upon completion of addition, the mixture was stirred for one hour at 10° C. and then a solution of 5.64 grams (0.025 mole) of tin (II) chloride dihydrate in 40 mL of concentrated hydrochloric acid was slowly added. Upon completion of addition, the reaction mixture was warmed to 25° C. where it stirred for one hour. At the conclusion of this period, 1.12 grams (0.010 mole) of trifluoroacetone was added and the resulting solid was collected by filtration, yielding 3.13 grams of title compound, m.p. 213-214° C. The NMR spectrum was consistent with the proposed structure. 
     Step B Compound 500 
     A stirred solution of 2.0 grams (0.0044 mole) of 3-[5-(1-trifluoromethylethylidenehydrazino)-4-chloro-2-fluorophenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione in 80 mL of polyphosphoric acid was heated at 80° C. for 20 minutes. After this time, the reaction mixture was allowed to cool to 25° C. where it was diluted with water. The resulting solid was collected by filtration, yielding 0.73 gram of Compound 500, m.p. 208-210° C. The NMR spectrum was consistent with the proposed structure. 
     EXAMPLE 9 
     SYNTHESIS OF 3-(7-CHLORO-2-ETHOXYCARBONYLINDOL4-YL)-4,5,6,7-TETRAHYDRO-1H-ISOINDOLE-1,3(2H)-DIONE (COMPOUND 595) 
     Step A 3-(1-ethoxycarbonylethylidenehydrazino)-4-chloronitrobenzene 
     This compound was prepared in the manner of Step A, Example 1, using, 17.25 grams (0.10 mole) of 2-chloro-5-nitroaniline, 6.9 grams (0.10 mole) of sodium nitrite, 56.4 grams (0.25 mole) of tin (II) chloride dihydrate, 11.61 grams (0.10 mole) of ethyl pyruvate, 30 mL of water, and 100 mL of concentrated hydrochloric acid. This preparation differs in that ethyl pyruvate was used rather than trifluoroacetone. The yield of title compound was 19.4 grams. The NMR spectrum was consistent with the proposed structure. 
     Step B 7-chloro-2-ethoxycarbonyl-4-nitroindole 
     This compound was prepared in the manner of Step B, Example 8, using 14.0 grams (0.050 mole) of 3-(1-ethoxycarbonylethylidenehydrazino)-4-chloronitrobenzene in 100 mL of polyphosphoric acid. The yield of title compound was 0.4 gram. The NMR spectrum was consistent with the proposed structure. 
     Step C 7-amino-4-chloro-2-ethoxycarbonylindole 
     A stirred solution of 2.68 grams (0.01 mole) of 4-chloro-2-ethoxycarbonyl-7-nitroindole, 80 mL of acetic acid, and 15 mL of water was heated to 65° C., and 18.3 grams (0.048 mole) of iron powder was slowly added during a 20 minute period. Upon completion of addition, the reaction mixture was allowed to cool to 25° C. where it stirred for one hour. After this time, the reaction mixture was poured into water, and the resulting mixture was filtered through diatomaceous earth. The filter cake was washed thoroughly with ethyl acetate. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure a residue. The residue was purified by column chromatography, yielding 0.4 gram of title compound. The NMR spectrum was consistent with the proposed structure. 
     Step D Compound 595 
     A stirred solution of 0.4 gram (0.0016 mole) of 7-amino-4-chloro-2-ethoxycarbonylindole and 0.26 gram (0.0016 mole) of 3,4,5,6-tetrahydrophhalic anhydride in 80 mL of acetic acid was heated at reflux for about 18 hours. After this time, the reaction mixture was extracted with several portions of diethyl ether. The organic extracts were combined, dried with magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel, yielding 0.47 gram of Compound 595. The NMR spectrum was consistent with the proposed structure. 
     
       
         
               
             
               
               
               
               
               
             
           
               
                 TABLE 1 
               
               
                   
               
             
             
               
                 Benzoxazoles 
               
               
                   
               
               
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 where A is nitrogen double bonded to position 2 and B is O; J is 
               
               
                   
               
               
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
             
          
           
               
                   
                 Compound No. 
                 X 
                 R 
                 R3 
               
               
                   
                   
               
               
                   
                 1 
                 4-Cl, 6-F 
                 CH 3   
                 CH 3   
               
               
                   
                 2 
                 4-Cl, 6-F 
                 CH 3   
                 C 2 H 5   
               
               
                   
                 3 
                 4-Cl, 6-F 
                 CH 3   
                 CH 2 CN 
               
               
                   
                 4 
                 4-Cl, 6-F 
                 CH 3   
                 CH 2 CH═CH 2   
               
               
                   
                 5 
                 4-Cl, 6-F 
                 CH 3   
                 NH 2   
               
               
                   
                 6 
                 4-Cl, 6-F 
                 CH 3   
                 CH 2 C≡CH 
               
               
                   
                 7 
                 4-Cl, 6-F 
                 CH 3   
                 C 3 H 7   
               
               
                   
                 8 
                 4-Cl, 6-F 
                 CH 3   
                 CH 2 OCH 3   
               
               
                   
                 9 
                 4-Cl, 6-F 
                 CH 3   
                 CH 2 CO 2 C 2 H 5   
               
               
                   
                   
               
             
          
         
       
     
     
       
         
               
             
               
               
               
             
               
               
               
               
               
             
               
               
               
               
               
               
               
             
           
               
                 TABLE 2 
               
               
                   
               
             
             
               
                   
               
               
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
             
          
           
               
                   
               
               
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
               
                 J1 
                 J2 
                 J3 
               
             
          
           
               
                   
                   
               
               
                   
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
                   
               
               
                   
                 J4 
                 J5 
                 J6 
                 J7 
               
             
          
           
               
                   
                   
                   
                 Double Bond 
                   
                   
                   
               
               
                 No. 
                 A 
                 B 
                 Posit&#39;n 
                 X 
                 R 
                 J 
               
               
                   
               
               
                  10 
                 N 
                 O 
                 1-2 
                 4-Cl 
                 CH 3   
                 J1 
               
               
                  11 
                 N 
                 O 
                 1-2 
                 4-Cl 
                 C 2 H 5   
                 J1 
               
               
                  12 
                 N 
                 O 
                 1-2 
                 4-Cl 
                 CH(CH 3 ) 2   
                 J1 
               
               
                  13 
                 N 
                 O 
                 1-2 
                 4,6-Cl 2   
                 CH 3   
                 J1 
               
               
                  14 
                 N 
                 O 
                 1-2 
                 4,6-Cl 2   
                 C 2 H 5   
                 J1 
               
               
                  15 
                 N 
                 O 
                 1-2 
                 4,6-Cl 2   
                 C 2 H 5   
                 J1 
               
               
                  16 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 CH 3   
                 J1 
               
               
                  17 
                 N 
                 O 
                 1-2 
                 4-CF 3 , 6-F 
                 CH 3   
                 J1 
               
               
                  18 
                 N 
                 O 
                 1-2 
                 4,6-F 2   
                 CH 3   
                 J1 
               
               
                  19 
                 N 
                 O 
                 1-2 
                 4-CN, 6-F 
                 CH 3   
                 J1 
               
               
                  20 
                 N 
                 O 
                 1-2 
                 4-OCF 3 , 6-F 
                 CH 3   
                 J1 
               
               
                  21 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 C 2 H 5   
                 J1 
               
               
                  22 
                 N 
                 O 
                 1-2 
                 4-CN, 6-F 
                 C 2 H 5   
                 J1 
               
               
                  23 
                 N 
                 O 
                 1-2 
                 4-CN, 6-F 
                 CH(CH 3 ) 2   
                 J1 
               
               
                  24 
                 N 
                 O 
                 1-2 
                 4-CH 3 , 6-F 
                 CH 3   
                 J1 
               
               
                  25 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                  26 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C 3 H 7   
                 J1 
               
               
                  27 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C 4 H 9   
                 J1 
               
               
                  28 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH(CH 3 ) 2   
                 J1 
               
               
                  29 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 CH(CH 3 ) 2   
                 J1 
               
               
                  30 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 3   
                 J1 
               
               
                  31 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 phenyl 
                 J1 
               
               
                  32 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 phenylmethyl 
                 J1 
               
               
                  33 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                  34 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CCl 2   
                 J1 
               
               
                  35 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 Cl 
                 J1 
               
               
                  36 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OH 
                 J1 
               
               
                  37 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 Br 
                 J1 
               
               
                  38 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 NH 2   
                 J1 
               
               
                  39 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 NHCH 3   
                 J1 
               
               
                  40 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 N(CH 3 ) 2   
                 J1 
               
               
                  41 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 NHCH 2 CO 2 CH 3   
                 J1 
               
               
                  42 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 NHSO 2 CH 3   
                 J1 
               
               
                  43 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 NHCOCH 3   
                 J1 
               
               
                  44 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 morpholino 
                 J1 
               
               
                  45 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 NHSO 2 C 6 H 5   
                 J1 
               
               
                  46 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 NHSO 2 CH 2 C 6 H 5   
                 J1 
               
               
                  47 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 N(CH 3 )SO 2 CH 3   
                 J1 
               
               
                  48 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 NHPO(OCH 3 ) 2   
                 J1 
               
               
                  49 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 CH 2 CO 2 CH 3   
                 J1 
               
               
                  50 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 4 CO 2 CH 3   
                 J1 
               
               
                  51 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH═CHCO 2 CH 3   
                 J1 
               
               
                  52 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH═C(Cl)CO 2 CH 3   
                 J1 
               
               
                  53 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 CH(Cl)CO 2 CH 3   
                 J1 
               
               
                  54 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 3   
                 J1 
               
               
                  55 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OC 2 H 5   
                 J1 
               
               
                  56 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH(CH 3 ) 2   
                 J1 
               
               
                  57 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 CH═CH 2   
                 J1 
               
               
                  58 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 C(CH 3 )═CH 2   
                 J1 
               
               
                  59 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 CCH 
                 J1 
               
               
                  60 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 CO 2 C 2 H 5   
                 J1 
               
               
                  61 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH(CH 3 )CO 2 CH 3   
                 J1 
               
               
                  62 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 CN 
                 J1 
               
               
                  63 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 CONH 2   
                 J1 
               
               
                  64 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 CONHCH 3   
                 J1 
               
               
                  65 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH(CH 3 )CONH 2   
                 J1 
               
               
                  66 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH(CH 3 )CONHCH 3   
                 J1 
               
               
                  67 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 CO 2 H 
                 J1 
               
               
                  68 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 phenoxy 
                 J1 
               
               
                  69 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 p-OC 6 H 4 OCH(CH 3 )CO 2 CH 3   
                 J1 
               
               
                  70 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 4-chlorophenoxy 
                 J1 
               
               
                  71 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 phenylmethoxy 
                 J1 
               
               
                  72 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CN 
                 J1 
               
               
                  73 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J1 
               
               
                  74 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 H 
                 J1 
               
               
                  75 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 Na 
                 J1 
               
               
                  76 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CONH 2   
                 J1 
               
               
                  77 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CONHCH 3   
                 J1 
               
               
                  78 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CON(CH 3 ) 2   
                 J1 
               
               
                  79 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CONHSO 2 CH 3   
                 J1 
               
               
                  80 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 NHOCH 3   
                 J1 
               
               
                  81 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 SCH 3   
                 J1 
               
               
                  82 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 SCH 2 CO 2 CH 3   
                 J1 
               
               
                  83 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 SCH 2 CONH 2   
                 J1 
               
               
                  84 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 SO 2 CH 3   
                 J1 
               
               
                  85 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 SH 
                 J1 
               
               
                  86 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 OH 
                 J1 
               
               
                  87 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH(CH 3 )OH 
                 J1 
               
               
                  88 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OH 
                 J1 
               
               
                  89 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 4 OH 
                 J1 
               
               
                  90 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 CH(CH 3 )OH 
                 J1 
               
               
                  91 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 C(CH 3 ) 2 OH 
                 J1 
               
               
                  92 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OCOCH 3   
                 J1 
               
               
                  93 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH(CH 3 ) 2 OCOCH 3   
                 J1 
               
               
                  94 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH(CH 3 )OCOCH 3   
                 J1 
               
               
                  95 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CHBr 2   
                 J1 
               
               
                  96 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 CH 2 OCH 3   
                 J1 
               
               
                  97 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 OCH 2 CCH 
                 J1 
               
               
                  98 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 NH 2   
                 J1 
               
               
                  99 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 phenoxymethyl 
                 J1 
               
               
                 100 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 N(COCH 3 ) 2   
                 J1 
               
               
                 101 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 CH 2 OCOCH 3   
                 J1 
               
               
                 102 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 4-chlorophenoxymethyl 
                 J1 
               
               
                 103 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 CH(Ph)OCOCH 3   
                 J1 
               
               
                 104 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 C(CH 3 ) 2 OCOCH 3   
                 J1 
               
               
                 105 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 CO 2 H 
                 J1 
               
               
                 106 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 OCH 2 CCH 
                 J1 
               
               
                 107 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 OCH(CH 3 ) 2   
                 J1 
               
               
                 108 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 NHSO 2 CH 3   
                 J1 
               
               
                 109 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 OCH 3   
                 J1 
               
               
                 110 
                 N 
                 O 
                 1-2 
                 4-Br, 6-F 
                 OCH 2 CH═CH 2   
                 J1 
               
               
                 111 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 (CH 3 )(CN)OH 
                 J1 
               
               
                 112 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J2 
               
               
                 113 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 n-C 3 H 7   
                 J2 
               
               
                 114 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 i-C 3 H 7   
                 J2 
               
               
                 115 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 t-C 4 H 9   
                 J2 
               
               
                 116 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J2 
               
               
                 117 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 CO 2 CH 3   
                 J2 
               
               
                 118 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 phenoxymethyl 
                 J2 
               
               
                 119 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CONHCH 3   
                 J2 
               
               
                 120 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CON(CH 3 ) 2   
                 J2 
               
               
                 121 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J2 
               
               
                 122 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 Phenyl 
                 J2 
               
               
                 123 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 SCH 3   
                 J2 
               
               
                 124 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 OCH 3   
                 J2 
               
               
                 125 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 Benzyl 
                 J2 
               
               
                 126 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 4-chlorophenylmethyl 
                 J2 
               
               
                 127 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 SO 2 CH 3   
                 J2 
               
               
                 128 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J2 
               
               
                 129 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OCO 2 CH 3   
                 J2 
               
               
                 130 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 CH 2 OH 
                 J2 
               
               
                 131 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J3 
               
               
                 132 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 n-C 3 H 7   
                 J3 
               
               
                 133 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 i-C 3 H 7   
                 J3 
               
               
                 134 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 t-C 4 H 9   
                 J3 
               
               
                 135 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 OH 
                 J3 
               
               
                 136 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 CH 2 OH 
                 J3 
               
               
                 137 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OH 
                 J3 
               
               
                 138 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CONHCH 3   
                 J3 
               
               
                 139 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CON(CH 3 ) 2   
                 J3 
               
               
                 140 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J3 
               
               
                 141 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 Phenyl 
                 J3 
               
               
                 142 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 SCH 3   
                 J3 
               
               
                 143 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 OCH 3   
                 J3 
               
               
                 144 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 Benzyl 
                 J3 
               
               
                 145 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 4-chlorophenylmethyl 
                 J3 
               
               
                 146 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 SO 2 CH 3   
                 J3 
               
               
                 147 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J3 
               
               
                 148 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OCO 2 CH 3   
                 J3 
               
               
                 149 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 CH 2 OH 
                 J3 
               
               
                 150 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 CH 2 OCH 3   
                 J3 
               
               
                 151 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J3 
               
               
                 152 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 Na 
                 J3 
               
               
                 153 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CONHSO 2 CH 3   
                 J3 
               
               
                 154 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 CO 2 CH 3   
                 J3 
               
               
                 155 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH(CH 3 )CO 2 CH 3   
                 J3 
               
               
                 156 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 CH═CH 2   
                 J3 
               
               
                 157 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 CCH 
                 J3 
               
               
                 158 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OH 
                 J3 
               
               
                 159 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 3   
                 J3 
               
               
                 160 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH(CH 3 ) 2   
                 J3 
               
               
                 161 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J4 
               
               
                 162 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 n-C 3 H 7   
                 J4 
               
               
                 163 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 i-C 3 H 7   
                 J4 
               
               
                 164 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 t-C 4 H 9   
                 J4 
               
               
                 165 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 OH 
                 J4 
               
               
                 166 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 CH 2 OH 
                 J4 
               
               
                 167 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OH 
                 J4 
               
               
                 168 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CONHCH 3   
                 J4 
               
               
                 169 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CON(CH 3 ) 2   
                 J4 
               
               
                 170 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J4 
               
               
                 171 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 Phenyl 
                 J4 
               
               
                 172 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 SCH 3   
                 J4 
               
               
                 173 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 OCH 3   
                 J4 
               
               
                 174 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 Benzyl 
                 J4 
               
               
                 175 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 4-chlorophenylmethyl 
                 J4 
               
               
                 176 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 SO 2 CH 3   
                 J4 
               
               
                 177 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J4 
               
               
                 178 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OCO 2 CH 3   
                 J4 
               
               
                 179 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 CH 2 OH 
                 J4 
               
               
                 180 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 CH 2 OCH 3   
                 J4 
               
               
                 181 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J4 
               
               
                 182 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 Na 
                 J4 
               
               
                 183 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CONHSO 2 CH 3   
                 J4 
               
               
                 184 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 CO 2 CH 3   
                 J4 
               
               
                 185 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH(CH 3 )CO 2 CH 3   
                 J4 
               
               
                 186 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 CH═CH 2   
                 J4 
               
               
                 187 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 C≡CH 
                 J4 
               
               
                 188 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OH 
                 J4 
               
               
                 189 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 3   
                 J4 
               
               
                 190 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH(CH 3 ) 2   
                 J4 
               
               
                 191 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J5 
               
               
                 192 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 n-C 3 H 7   
                 J5 
               
               
                 193 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 i-C 3 H 7   
                 J5 
               
               
                 194 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 t-C 4 H 9   
                 J5 
               
               
                 195 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 OH 
                 J5 
               
               
                 196 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 CH 2 OH 
                 J5 
               
               
                 197 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OH 
                 J5 
               
               
                 198 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CONHCH 3   
                 J5 
               
               
                 199 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CON(CH 3 ) 2   
                 J5 
               
               
                 200 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J5 
               
               
                 201 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 Phenyl 
                 J5 
               
               
                 202 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 SCH 3   
                 J5 
               
               
                 203 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 OCH 3   
                 J5 
               
               
                 204 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 Benzyl 
                 J5 
               
               
                 205 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 4-chlorophenylmethyl 
                 J5 
               
               
                 206 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 SO 2 CH 3   
                 J5 
               
               
                 207 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J5 
               
               
                 208 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OCO 2 CH 3   
                 J5 
               
               
                 209 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 CH 2 OH 
                 J5 
               
               
                 210 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 CH 2 OCH 3   
                 J5 
               
               
                 211 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J5 
               
               
                 212 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 Na 
                 J5 
               
               
                 213 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CONHSO 2 CH 3   
                 J5 
               
               
                 214 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 CO 2 CH 3   
                 J5 
               
               
                 215 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH(CH 3 )CO 2 CH 3   
                 J5 
               
               
                 216 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 CH═CH 2   
                 J5 
               
               
                 217 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 2 CCH 
                 J5 
               
               
                 218 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OH 
                 J5 
               
               
                 219 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH 3   
                 J5 
               
               
                 220 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 OCH(CH 3 ) 2   
                 J5 
               
               
                 221 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 CH 3   
                 J1 
               
               
                 222 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 223 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 n-propyl 
                 J1 
               
               
                 224 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 225 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 n-butyl 
                 J1 
               
               
                 226 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 t-butyl 
                 J1 
               
               
                 227 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 228 
                 O 
                 CH 
                 2-3 
                 4,6-F 2   
                 t-butyl 
                 J1 
               
               
                 229 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )C 3 H 7   
                 J1 
               
               
                 230 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH═CH 2   
                 J1 
               
               
                 231 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 )═CH 2   
                 J1 
               
               
                 232 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 CH 2 Br 
                 J1 
               
               
                 233 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 CHBr 2   
                 J1 
               
               
                 234 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(Cl)CH 3   
                 J1 
               
               
                 235 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(F)CH 3   
                 J1 
               
               
                 236 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 Cl 
                 J1 
               
               
                 237 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 F 
                 J1 
               
               
                 238 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 CH 2 OH 
                 J1 
               
               
                 239 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 OH 
                 J1 
               
               
                 240 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OH 
                 J1 
               
               
                 241 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 C(CH 3 ) 2 OH 
                 J1 
               
               
                 242 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OH 
                 J1 
               
               
                 243 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH(CH 3 )OH 
                 J1 
               
               
                 244 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OC(CH 3 ) 3   
                 J1 
               
               
                 245 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(OC 2 H 5 ) 2   
                 J1 
               
               
                 246 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OCOCH 3   
                 J1 
               
               
                 247 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OCOCH(CH 3 ) 2   
                 J1 
               
               
                 248 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OCOPh 
                 J1 
               
               
                 249 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OCONHCH 3   
                 J1 
               
               
                 250 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OCONHCH 2 Ph 
                 J1 
               
               
                 251 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 C(CH 3 ) 2 OCH 3   
                 J1 
               
               
                 252 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OCH 2 OCH 3   
                 J1 
               
               
                 253 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OCOCH 3   
                 J1 
               
               
                 254 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 NH 2   
                 J1 
               
               
                 255 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 NHSO 2 CH 3   
                 J1 
               
               
                 256 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 CH 2 CN 
                 J1 
               
               
                 257 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 CH 2 N(C 2 H 5 ) 2   
                 J1 
               
               
                 258 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 CH═NOH 
                 J1 
               
               
                 259 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 CH═NOCH 3   
                 J1 
               
               
                 260 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 OCOCH 3   
                 J1 
               
               
                 261 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 OCONHCH 3   
                 J1 
               
               
                 262 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 CO 2 H 
                 J1 
               
               
                 263 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 CO 2 CH 3   
                 J1 
               
               
                 264 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 Phenyl 
                 J1 
               
               
                 265 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 CHO 
                 J1 
               
               
                 266 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 CO 2 H 
                 J1 
               
               
                 267 
                 O 
                 CH 
                 2-3 
                 H 
                 CO 2 C 2 H 5   
                 J1 
               
               
                 268 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 CO 2 C 2 H 5   
                 J1 
               
               
                 269 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 CONH 2   
                 J1 
               
               
                 270 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 CONHCH 3   
                 J1 
               
               
                 271 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 CON(CH 3 ) 2   
                 J1 
               
               
                 272 
                 O 
                 CH 
                 2-3 
                 4-Cl 
                 NHCO 2 C(CH 3 ) 3   
                 J1 
               
               
                 273 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CONH 2   
                 J1 
               
               
                 274 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CONH(CH 3 ) 
                 J1 
               
               
                 275 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CON(CH 3 ) 2   
                 J1 
               
               
                 276 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CO 2 H 
                 J1 
               
               
                 277 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J1 
               
               
                 278 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 OH 
                 J1 
               
               
                 279 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 3,4-dimethoxyphenyl 
                 J1 
               
               
                 280 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 Phenyl 
                 J1 
               
               
                 281 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J2 
               
               
                 282 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 n-propyl 
                 J2 
               
               
                 283 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 Isopropyl 
                 J2 
               
               
                 284 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J2 
               
               
                 285 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )C 3 H 7   
                 J2 
               
               
                 286 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH═CH 2   
                 J2 
               
               
                 287 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 )═CH 2   
                 J2 
               
               
                 288 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(Cl)CH 3   
                 J2 
               
               
                 289 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(F)CH 3   
                 J2 
               
               
                 290 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 Cl 
                 J2 
               
               
                 291 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 F 
                 J2 
               
               
                 292 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 OH 
                 J2 
               
               
                 293 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OH 
                 J2 
               
               
                 294 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OH 
                 J2 
               
               
                 295 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH(CH 3 )OH 
                 J2 
               
               
                 296 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OC(CH 3 ) 3   
                 J2 
               
               
                 297 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(OC 2 H 5 ) 2   
                 J2 
               
               
                 298 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OCOCH 3   
                 J2 
               
               
                 299 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OCOCH(CH 3 ) 2   
                 J2 
               
               
                 300 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OCOPh 
                 J2 
               
               
                 301 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OCONHCH 3   
                 J2 
               
               
                 302 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OCONHCH 2 Ph 
                 J2 
               
               
                 303 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OCH 2 OCH 3   
                 J2 
               
               
                 304 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OCOCH 3   
                 J2 
               
               
                 305 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 NH 2   
                 J2 
               
               
                 306 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 NHSO 2 CH 3   
                 J2 
               
               
                 307 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 CH 2 CN 
                 J2 
               
               
                 308 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 OCOCH 3   
                 J2 
               
               
                 309 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 OCONHCH 3   
                 J2 
               
               
                 310 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 CO 2 H 
                 J2 
               
               
                 311 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 CO 2 CH 3   
                 J2 
               
               
                 312 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CONH 2   
                 J2 
               
               
                 313 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CONH(CH 3 ) 
                 J2 
               
               
                 314 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CON(CH 3 ) 2   
                 J2 
               
               
                 315 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CO 2 H 
                 J2 
               
               
                 316 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J2 
               
               
                 317 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 OH 
                 J2 
               
               
                 318 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 3,4-dimethoxyphenyl 
                 J2 
               
               
                 319 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 Phenyl 
                 J2 
               
               
                 320 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J3 
               
               
                 321 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J3 
               
               
                 322 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(Cl)CH 3   
                 J3 
               
               
                 323 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(F)CH 3   
                 J3 
               
               
                 324 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 Cl 
                 J3 
               
               
                 325 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 F 
                 J3 
               
               
                 326 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 OH 
                 J3 
               
               
                 327 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OH 
                 J3 
               
               
                 328 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OH 
                 J3 
               
               
                 329 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OCH 2 OCH 3   
                 J3 
               
               
                 330 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 NHSO 2 CH 3   
                 J3 
               
               
                 331 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 CH 2 CN 
                 J3 
               
               
                 332 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 CO 2 CH 3   
                 J3 
               
               
                 333 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CON(CH 3 ) 2   
                 J3 
               
               
                 334 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J4 
               
               
                 335 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J4 
               
               
                 336 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(Cl)CH 3   
                 J4 
               
               
                 337 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(F)CH 3   
                 J4 
               
               
                 338 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 Cl 
                 J4 
               
               
                 339 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 F 
                 J4 
               
               
                 340 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 OH 
                 J4 
               
               
                 341 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OH 
                 J4 
               
               
                 342 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OH 
                 J4 
               
               
                 343 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OCH 2 OCH 3   
                 J4 
               
               
                 344 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 NHSO 2 CH 3   
                 J4 
               
               
                 345 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 CH 2 CN 
                 J4 
               
               
                 346 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 CO 2 CH 3   
                 J4 
               
               
                 347 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CON(CH 3 ) 2   
                 J4 
               
               
                 348 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J5 
               
               
                 349 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J5 
               
               
                 350 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(Cl)CH 3   
                 J5 
               
               
                 351 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(F)CH 3   
                 J5 
               
               
                 352 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 Cl 
                 J5 
               
               
                 353 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 F 
                 J5 
               
               
                 354 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 OH 
                 J5 
               
               
                 355 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OH 
                 J5 
               
               
                 356 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OH 
                 J5 
               
               
                 357 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OCH 2 OCH 3   
                 J5 
               
               
                 358 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 NHSO 2 CH 3   
                 J5 
               
               
                 359 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 CH 2 CN 
                 J5 
               
               
                 360 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 CO 2 CH 3   
                 J5 
               
               
                 361 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CON(CH 3 ) 2   
                 J5 
               
               
                 362 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 H 
                 J1 
               
               
                 363 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 364 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CHF 2   
                 J1 
               
               
                 365 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 366 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CClF 2   
                 J1 
               
               
                 367 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 368 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 i-C 3 H 7   
                 J1 
               
               
                 369 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 t-C 4 H 9   
                 J1 
               
               
                 370 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 OCH 3   
                 J1 
               
               
                 371 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OC(O)CH 3   
                 J1 
               
               
                 372 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 4 CO 2 C 2 H 5   
                 J1 
               
               
                 373 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 Cyclohexyl 
                 J1 
               
               
                 374 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 Adamantyl 
                 J1 
               
               
                 375 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 Phenyl 
                 J1 
               
               
                 376 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 Benzyl 
                 J1 
               
               
                 377 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )C 6 H 5   
                 J1 
               
               
                 378 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 OC 6 H 5   
                 J1 
               
               
                 379 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 4 C 6 H 5   
                 J1 
               
               
                 380 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C 3 H 6 C 6 H 5   
                 J1 
               
               
                 381 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 2-chlorophenylmethyl 
                 J1 
               
               
                 382 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 3-chlorophenylmethyl 
                 J1 
               
               
                 383 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 4-chlorophenylmethyl 
                 J1 
               
               
                 384 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J1 
               
               
                 385 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 Furan-2-yl 
                 J1 
               
               
                 386 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 Cl 
                 J1 
               
               
                 387 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 CH 2 Cl 
                 J1 
               
               
                 388 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 OC 2 H 5   
                 J1 
               
               
                 389 
                 N 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 390 
                 N 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 391 
                 N 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 392 
                 N 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 393 
                 N 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 394 
                 N 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J1 
               
               
                 395 
                 N 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 396 
                 N 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 397 
                 N 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 398 
                 N 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 399 
                 N 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 400 
                 N 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J1 
               
               
                 401 
                 N 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 2 CH 3   
                 J1 
               
               
                 402 
                 N 
                 NC 2 H 5   
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 403 
                 N 
                 NC 2 H 5   
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 404 
                 NH 
                 NH 
                 — 
                 4-NO 2 , 6-F 
                 CF 3   
                 J1 
               
               
                 405 
                 N − H 3 N + CH(CH 3 ) 2   
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 406 
                 NCH 3   
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 407 
                 NCH 3   
                 NC 2 H 5   
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 408 
                 N 
                 NC 2 H 5   
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 409 
                 N 
                 NC 2 H 5   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 410 
                 N 
                 NC 2 H 5   
                 1-2 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J1 
               
               
                 411 
                 N 
                 NC 4 H 9   
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 412 
                 N 
                 NC 4 H 9   
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 413 
                 N 
                 NC 4 H 9   
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 414 
                 N 
                 NC 4 H 9   
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 415 
                 N 
                 NC 4 H 9   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 416 
                 N 
                 NC 4 H 9   
                 1-2 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J1 
               
               
                 417 
                 N 
                 NCH 2 OCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 418 
                 N 
                 NCH 2 OCH 3   
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 419 
                 N 
                 NCH 2 OCH 3   
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 420 
                 N 
                 NCH 2 OCH 3   
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 421 
                 N 
                 NCH 2 OCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 422 
                 N 
                 NCH 2 OCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J1 
               
               
                 423 
                 N 
                 NCO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 424 
                 N 
                 NCO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 425 
                 N 
                 NCO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 426 
                 N 
                 NCO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 427 
                 N 
                 NCO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 428 
                 N 
                 NCO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J1 
               
               
                 429 
                 N 
                 NSO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 430 
                 N 
                 NSO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 431 
                 N 
                 NSO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 432 
                 N 
                 NSO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 433 
                 N 
                 NSO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 434 
                 N 
                 NSO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J1 
               
               
                 435 
                 N 
                 NCH 2 CHCH 2   
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 436 
                 N 
                 NCH 2 CHCH 2   
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 437 
                 N 
                 NCH 2 CHCH 2   
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 438 
                 N 
                 NCH 2 CHCH 2   
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 439 
                 N 
                 NCH 2 CHCH 2   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 440 
                 N 
                 NCH 2 CHCH 2   
                 1-2 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J1 
               
               
                 441 
                 N 
                 NCH 2 CCH 
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 442 
                 N 
                 NCH 2 CCH 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 443 
                 N 
                 NCH 2 CCH 
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 444 
                 N 
                 NCH 2 CCH 
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 445 
                 N 
                 NCH 2 CCH 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 446 
                 N 
                 NCH 2 CCH 
                 1-2 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J1 
               
               
                 447 
                 N 
                 NCH 2 CO 2 Me 
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 448 
                 N 
                 NCH 2 CO 2 Me 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 449 
                 N 
                 NCH 2 CO 2 Me 
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 450 
                 N 
                 NCH 2 CO 2 Me 
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 451 
                 N 
                 NCH 2 CO 2 Me 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 452 
                 N 
                 NCH 2 CO 2 Me 
                 1-2 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J1 
               
               
                 453 
                 N 
                 NCF 3   
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 454 
                 N 
                 NCF 3   
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 455 
                 N 
                 NCH 2 CO 2 Me 
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 456 
                 N 
                 NCH 2 CO 2 Me 
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 457 
                 N 
                 NCH 2 CO 2 Me 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 458 
                 N 
                 NCF 3   
                 1-2 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J1 
               
               
                 459 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J2 
               
               
                 460 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J2 
               
               
                 461 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 Isopropyl 
                 J2 
               
               
                 462 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J2 
               
               
                 463 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J2 
               
               
                 464 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J2 
               
               
                 465 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J3 
               
               
                 466 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J3 
               
               
                 467 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 Isopropyl 
                 J3 
               
               
                 468 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J3 
               
               
                 469 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J3 
               
               
                 470 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J3 
               
               
                 471 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J4 
               
               
                 472 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J4 
               
               
                 473 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 Isopropyl 
                 J4 
               
               
                 474 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J4 
               
               
                 475 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J4 
               
               
                 476 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J4 
               
               
                 477 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J5 
               
               
                 478 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J5 
               
               
                 479 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 Isopropyl 
                 J5 
               
               
                 480 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J5 
               
               
                 481 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J5 
               
               
                 482 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J5 
               
               
                 483 
                 NH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 484 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 n-C 3 H 7   
                 J1 
               
               
                 485 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 i-C 3 H 7   
                 J1 
               
               
                 486 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 t-C 4 H 9   
                 J1 
               
               
                 487 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 OH 
                 J1 
               
               
                 488 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 CH 2 OH 
                 J1 
               
               
                 489 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OH 
                 J1 
               
               
                 490 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CONHCH 3   
                 J1 
               
               
                 491 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CON(CH 3 ) 2   
                 J1 
               
               
                 492 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J1 
               
               
                 493 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 2 CH 3   
                 J1 
               
               
                 494 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 Phenyl 
                 J1 
               
               
                 495 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J1 
               
               
                 496 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 OCH 3   
                 J1 
               
               
                 497 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 Benzyl 
                 J1 
               
               
                 498 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 4-chlorophenylmethyl 
                 J1 
               
               
                 499 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 SO 2 CH 3   
                 J1 
               
               
                 500 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 501 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OCOCH 3   
                 J1 
               
               
                 502 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 CH 2 OH 
                 J1 
               
               
                 503 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 CH 2 OCH 3   
                 J1 
               
               
                 504 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 505 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 Na 
                 J1 
               
               
                 506 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CONHSO 2 CH 3   
                 J1 
               
               
                 507 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CHFCH 3   
                 J1 
               
               
                 508 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CH 2 CO 2 CH 2 CH 3   
                 J1 
               
               
                 509 
                 CH 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 510 
                 CH 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 511 
                 CH 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 512 
                 CH 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 513 
                 CH 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 514 
                 CH 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J1 
               
               
                 515 
                 CH 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CHFCH 3   
                 J1 
               
               
                 516 
                 CH 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CON(CH 3 ) 2   
                 J1 
               
               
                 517 
                 CH 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CH 2 CO 2 C 2 H 5   
                 J1 
               
               
                 518 
                 CH 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CH 2 CH 2 CN 
                 J1 
               
               
                 519 
                 CH 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OH 
                 J1 
               
               
                 520 
                 CH 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OCOCH 3   
                 J1 
               
               
                 521 
                 CH 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 NHSO 2 CH 3   
                 J1 
               
               
                 522 
                 CH 
                 NCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 2 CH 3   
                 J1 
               
               
                 523 
                 CH 
                 NC 2 H 5   
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 524 
                 CH 
                 NC 2 H 5   
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 525 
                 CH 
                 NC 2 H 5   
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 526 
                 CH 
                 NC 2 H 5   
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 527 
                 CH 
                 NC 2 H 5   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 528 
                 CH 
                 NC 2 H 5   
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J1 
               
               
                 529 
                 CH 
                 NC 4 H 9   
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 530 
                 CH 
                 NC 4 H 9   
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 531 
                 CH 
                 NC 4 H 9   
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 532 
                 CH 
                 NC 4 H 9   
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 533 
                 CH 
                 NC 4 H 9   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 534 
                 CH 
                 NC 4 H 9   
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J1 
               
               
                 535 
                 CH 
                 NCH 2 OCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 536 
                 CH 
                 NCH 2 OCH 3   
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 537 
                 CH 
                 NCO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 538 
                 CH 
                 NCH 2 OCH 3   
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 539 
                 CH 
                 NCH 2 OCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 540 
                 CH 
                 NCH 2 OCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J1 
               
               
                 541 
                 CH 
                 NCO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 542 
                 CH 
                 NCO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 543 
                 CH 
                 NCO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 544 
                 CH 
                 NCO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 545 
                 CH 
                 NCO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 546 
                 CH 
                 NCO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J1 
               
               
                 547 
                 CH 
                 NSO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 548 
                 CH 
                 NSO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 549 
                 CH 
                 NSO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 550 
                 CH 
                 NSO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 551 
                 CH 
                 NSO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 552 
                 CH 
                 NSO 2 CH 3   
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J1 
               
               
                 553 
                 CH 
                 NCH 2 CHCH 2   
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 554 
                 CH 
                 NCH 2 CHCH 2   
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 555 
                 CH 
                 NCH 2 CHCH 2   
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 556 
                 CH 
                 NCH 2 CHCH 2   
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 557 
                 CH 
                 NCH 2 CHCH 2   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 558 
                 CH 
                 NCH 2 CHCH 2   
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J1 
               
               
                 559 
                 CH 
                 NCH 2 C≡CH 
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 560 
                 CH 
                 NCH 2 C≡CH 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 561 
                 CH 
                 NCH 2 C≡CH 
                 1-2 
                 4-Cl, 6-F 
                 Isopropyl 
                 J1 
               
               
                 562 
                 CH 
                 NCH 2 C≡CH 
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 563 
                 CH 
                 NCH 2 C≡CH 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 564 
                 CH 
                 NCH 2 C≡CH 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J1 
               
               
                 565 
                 CH 
                 NCH 2 CO 2 Me 
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 566 
                 CH 
                 NCH 2 CO 2 Me 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 567 
                 CH 
                 NCH 2 CO 2 Me 
                 1-2 
                 4-Cl, 6-F 
                 isopropyl 
                 J1 
               
               
                 568 
                 CH 
                 NCH 2 CO 2 Me 
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 569 
                 CH 
                 NCH 2 CO 2 Me 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 570 
                 CH 
                 NCH 2 CO 2 Me 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J1 
               
               
                 571 
                 CH 
                 NCH 2 CHF 2   
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 572 
                 CH 
                 NCH 2 CHF 2   
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 573 
                 CH 
                 NCH 2 CHF 2   
                 1-2 
                 4-Cl, 6-F 
                 isopropyl 
                 J1 
               
               
                 574 
                 CH 
                 NCH 2 CHF 2   
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 575 
                 CH 
                 NCH 2 CHF 2   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 576 
                 CH 
                 NCH 2 CHF 2   
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J1 
               
               
                 577 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J2 
               
               
                 578 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J2 
               
               
                 579 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 isopropyl 
                 J2 
               
               
                 580 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J2 
               
               
                 581 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J2 
               
               
                 582 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J2 
               
               
                 583 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J3 
               
               
                 584 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J3 
               
               
                 585 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 isopropyl 
                 J3 
               
               
                 586 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J3 
               
               
                 587 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J3 
               
               
                 588 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J3 
               
               
                 589 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J4 
               
               
                 590 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J4 
               
               
                 591 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 isopropyl 
                 J4 
               
               
                 592 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J4 
               
               
                 593 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J4 
               
               
                 594 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J4 
               
               
                 595 
                 CH 
                 NH 
                 1-2 
                 4-Cl 
                 CO 2 CH 2 CH 3   
                 J5 
               
               
                 596 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J5 
               
               
                 597 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 C 2 H 3   
                 J5 
               
               
                 598 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 isopropyl 
                 J5 
               
               
                 599 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 t-butyl 
                 J5 
               
               
                 600 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J5 
               
               
                 601 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J5 
               
               
                 602 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J7 
               
               
                 603 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 n-C 3 H 7   
                 J1 
               
               
                 604 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 i-C 3 H 7   
                 J1 
               
               
                 605 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 t-C 4 H 9   
                 J1 
               
               
                 606 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 OH 
                 J1 
               
               
                 607 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CH 2 OH 
                 J1 
               
               
                 608 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OH 
                 J1 
               
               
                 609 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CONHCH 3   
                 J1 
               
               
                 610 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CON(CH 3 ) 2   
                 J1 
               
               
                 611 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J1 
               
               
                 612 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 Phenyl 
                 J1 
               
               
                 613 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CF 2 CF 3   
                 J1 
               
               
                 614 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 OCH 3   
                 J1 
               
               
                 615 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 Benzyl 
                 J1 
               
               
                 616 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 4-chlorophenylmethyl 
                 J1 
               
               
                 617 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 SO 2 CH 3   
                 J1 
               
               
                 618 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 619 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OCOCH 3   
                 J1 
               
               
                 620 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 CH 2 OH 
                 J1 
               
               
                 621 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 CH 2 OCH 3   
                 J1 
               
               
                 622 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 623 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CO 2 Na 
                 J1 
               
               
                 624 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CONHSO 2 CH 3   
                 J1 
               
               
                 625 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CHFCH 3   
                 J1 
               
               
                 626 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CO 2 CH 2 CH 3   
                 J1 
               
               
                 627 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J2 
               
               
                 628 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J2 
               
               
                 629 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 isopropyl 
                 J2 
               
               
                 630 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J2 
               
               
                 631 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J2 
               
               
                 632 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J2 
               
               
                 633 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J3 
               
               
                 634 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J3 
               
               
                 635 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 isopropyl 
                 J3 
               
               
                 636 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J3 
               
               
                 637 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J3 
               
               
                 638 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J3 
               
               
                 639 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J4 
               
               
                 640 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J4 
               
               
                 641 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 isopropyl 
                 J4 
               
               
                 642 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J4 
               
               
                 643 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J4 
               
               
                 644 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J4 
               
               
                 645 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J5 
               
               
                 646 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J5 
               
               
                 647 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 isopropyl 
                 J5 
               
               
                 648 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J5 
               
               
                 649 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J5 
               
               
                 650 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J5 
               
               
                 651 
                 NH 
                 CCH 3   
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 652 
                 NH 
                 CCH 3   
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 653 
                 NH 
                 CCH 3   
                 2-3 
                 4-Cl, 6-F 
                 isopropyl 
                 J1 
               
               
                 654 
                 NH 
                 CCH 3   
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 655 
                 NH 
                 CCH 3   
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 656 
                 NH 
                 CCH 3   
                 2-3 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J1 
               
               
                 657 
                 NH 
                 CCH 2 CH 3   
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 658 
                 NH 
                 CCH 2 CH 3   
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 659 
                 NH 
                 CCH 2 CH 3   
                 2-3 
                 4-Cl, 6-F 
                 isopropyl 
                 J1 
               
               
                 660 
                 NH 
                 CCH 2 CH 3   
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 661 
                 NH 
                 CCH 2 CH 3   
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 662 
                 NH 
                 CCH 2 CH 3   
                 2-3 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J1 
               
               
                 663 
                 NH 
                 CCH 2 CHF 2   
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J1 
               
               
                 664 
                 NH 
                 CCH 2 CHF 2   
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 665 
                 NH 
                 CCH 2 CHF 2   
                 2-3 
                 4-Cl, 6-F 
                 isopropyl 
                 J1 
               
               
                 666 
                 NH 
                 CCH 2 CHF 2   
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J1 
               
               
                 667 
                 NH 
                 CCH 2 CHF 2   
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 668 
                 NH 
                 CCH 2 CHF 2   
                 2-3 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J1 
               
               
                 669 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J2 
               
               
                 670 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J2 
               
               
                 671 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 isopropyl 
                 J2 
               
               
                 672 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J2 
               
               
                 673 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J2 
               
               
                 674 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J2 
               
               
                 675 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J3 
               
               
                 676 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J3 
               
               
                 677 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 isopropyl 
                 J3 
               
               
                 678 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J3 
               
               
                 679 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J3 
               
               
                 680 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J3 
               
               
                 681 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J4 
               
               
                 682 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J4 
               
               
                 683 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 isopropyl 
                 J4 
               
               
                 684 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J4 
               
               
                 685 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J4 
               
               
                 686 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J4 
               
               
                 687 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 3   
                 J5 
               
               
                 688 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J5 
               
               
                 689 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 isoprcpyl 
                 J5 
               
               
                 690 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 t-butyl 
                 J5 
               
               
                 691 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J5 
               
               
                 692 
                 NH 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CO 2 CH 3   
                 J5 
               
               
                 693 
                 NCH 3   
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 694 
                 NH 
                 CH 
                 2-3 
                 4-Cl 
                 CF 3   
                 J1 
               
               
                 695 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 696 
                 CH 
                 NCH 2 C 6 H 5   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 697 
                 CH 
                 NCH 2 CO 2 C 2 H 5   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 698 
                 CH 
                 NCOCH 3   
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 699 
                 CH 
                 NCH 2 C≡N 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 700 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 701 
                 CH 
                 NH 
                 1-2 
                 4-Cl, 6-F 
                 CO 2 C 2 H 5   
                 J1 
               
               
                 702 
                 CH 
                 NH 
                 1-2 
                 4-Cl 
                 CO 2 C 2 H 5   
                 J1 
               
               
                 703 
                 N 
                 O 
                 1-2 
                 4-Cl, 6-F 
                 CH 3   
                 J7 
               
               
                 704 
                 O 
                 CH 
                 1-2 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OH 
                 J7 
               
               
                 705 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J6 
               
               
                 706 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 3   
                 J6 
               
               
                 707 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CF 3   
                 J7 
               
               
                 708 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 C(CH 3 ) 3   
                 J1 
               
               
                 709 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 3,5-dimethylisoxazolyl 
                 J1 
               
               
                 710 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 pyridin-2-yl 
                 J1 
               
               
                 711 
                 NCOCH 3   
                 N 
                 2-3 
                 4-Cl, 6-F 
                 H 
                 J1 
               
               
                 712 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C 7 F 15   
                 J1 
               
               
                 713 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CHCl 2   
                 J1 
               
               
                 714 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 NHCO 2 C 2 H 5   
                 J1 
               
               
                 715 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )NHCH 2 CO 2 C 2 H 5   
                 J1 
               
               
                 716 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH(CH 3 )OCOCH 3   
                 J1 
               
               
                 717 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 )═CH 2   
                 J1 
               
               
                 718 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH═C(CH 3 ) 2   
                 J1 
               
               
                 719 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH(Br)CH 3   
                 J1 
               
               
                 720 
                 NH 
                 N 
                 2-3 
                 6-F 
                 CF 3   
                 J1 
               
               
                 721 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH═NC 6 H 5   
                 J1 
               
               
                 722 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 OCOCH 3   
                 J1 
               
               
                 723 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH(OCH 3 )C 6 H 5   
                 J1 
               
               
                 724 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH(OCOCH 3 )C 6 H 5   
                 J1 
               
               
                 725 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 SCH 3   
                 J1 
               
               
                 726 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 5   
                 J5 
               
               
                 727 
                 NCH 3   
                 N 
                 2-3 
                 4,6-Cl 2   
                 CF 3   
                 J1 
               
               
                 728 
                 N 
                 NCH 3   
                 2-3 
                 4,6-Cl 2   
                 CF 3   
                 J1 
               
               
                 729 
                 NH 
                 NH 
                 — 
                 4-Cl, 6-F 
                 CF 3   
                 J1 
               
               
                 730 
                 NH 
                 N 
                 2-3 
                 4,6-Cl 2   
                 CF 3   
                 J5 
               
               
                 731 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 SO 2 CH 3   
                 J1 
               
               
                 732 
                 NH 
                 N 
                 2-3 
                 4-Br, 6-F 
                 CF 3   
                 J1 
               
               
                 733 
                 NH 
                 N 
                 2-3 
                 4-Br, 6-F 
                 C 2 H 5   
                 J1 
               
               
                 734 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 OH 
                 J1 
               
               
                 735 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 OH 
                 J1 
               
               
                 736 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 )OCH 2 C 6 H 5   
                 J1 
               
               
                 737 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 SH 
                 J1 
               
               
                 738 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 SCH(CH 3 )C≡N 
                 J1 
               
               
                 739 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 SC 2 H 5   
                 J1 
               
               
                 740 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 SCH 2 C≡CH 
                 J1 
               
               
                 741 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 SCH 2 C 6 H 5   
                 J1 
               
               
                 742 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 SC≡N 
                 J1 
               
               
                 743 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 CH 2 SC≡N 
                 J1 
               
               
                 744 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 SCH(CH 3 )CO 2 C 2 H 5   
                 J1 
               
               
                 745 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 SCH(CH 3 )CON(CH 3 ) 2   
                 J1 
               
               
                 746 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 SCH 2 C≡CH 
                 J5 
               
               
                 747 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 SCH 2 CH═CH 2   
                 J1 
               
               
                 748 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 SCH 2 C≡N 
                 J1 
               
               
                 749 
                 NH 
                 N 
                 2-3 
                 4-Cl, 6-F 
                 SCH 2 C≡CCH 2 Cl 
                 J1 
               
               
                 750 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 OCONHCH 3   
                 J1 
               
               
                 751 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 NHCOCH 2 (C 6 H 4 , 2-NO 2 ) 
                 J1 
               
               
                 752 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 )(OH)C 6 H 5   
                 J1 
               
               
                 753 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 NH 2   
                 J1 
               
               
                 754 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 )(OH)CH(CH 3 ) 2   
                 J1 
               
               
                 755 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 NHCOCH 3   
                 J1 
               
               
                 756 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 NHSO 2 CH 3   
                 J1 
               
               
                 757 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C(CH 3 ) 2 F 
                 J1 
               
               
                 758 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CO 2 H 
                 J1 
               
               
                 759 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CON(CH 3 ) 2   
                 J1 
               
               
                 760 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CON(CH 3 )(OCH 3 ) 
                 J1 
               
               
                 761 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CONHCH 3   
                 J1 
               
               
                 762 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 CH 2 CONH 2   
                 J1 
               
               
                 763 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 4 CON(CH 3 )(OCH 3 ) 
                 J1 
               
               
                 764 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 4 CO 2 CH 3   
                 J1 
               
               
                 765 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C 3 H 6 OH 
                 J1 
               
               
                 766 
                 O 
                 CH 
                 2-3 
                 4-Cl, 6-F 
                 C 2 H 4 CONHCH 3   
                 J1 
               
               
                 767 
                 NH 
                 N 
                 2-3 
                 4-Cl 
                 SCF 3   
                 J1 
               
               
                 768 
                 NH 
                 N 
                 2-3 
                 4-Cl 
                 CF 3   
                 J1 
               
               
                 769 
                 NH 
                 N 
                 2-3 
                 4-Cl 
                 CF 3   
                 J3 
               
               
                   
               
             
          
         
       
     
     
       
         
               
             
               
               
             
           
               
                 TABLE 3 
               
             
             
               
                   
               
               
                 Characterizing Data 
               
               
                 Melting Points or Physical States of Representative Compounds 
               
             
          
           
               
                 No. 
                 MP/State 
               
               
                   
               
               
                  1 
                 OIL 
               
               
                 16 
                 70-72 
               
               
                 25 
                 OIL 
               
               
                 26 
                 OIL 
               
               
                 28 
                 OIL 
               
               
                 30 
                 OIL 
               
               
                 38 
                 246-9 
               
               
                 42 
                 &gt;250 
               
               
                 43 
                 SOLID 
               
               
                 49 
                 OIL 
               
               
                 96 
                 OIL 
               
               
                 98 
                 &gt;245 
               
               
                 99 
                 OIL 
               
               
                 100  
                 OIL 
               
               
                 101  
                 OIL 
               
               
                 102  
                 OIL 
               
               
                 103  
                 OIL 
               
               
                 104  
                 OIL 
               
               
                 105  
                 &gt;250 
               
               
                 106  
                 OIL 
               
               
                 107  
                 OIL 
               
               
                 108  
                 &gt;250 
               
               
                 109  
                 OIL 
               
               
                 110  
                 OIL 
               
               
                 112  
                 86-88 
               
               
                 221  
                 193.5-6 
               
               
                 222  
                 183-6 
               
               
                 223  
                 OIL 
               
               
                 224  
                 OIL 
               
               
                 225  
                 OIL 
               
               
                 226  
                 63-6 
               
               
                 227  
                 134-6 
               
               
                 228  
                 42-5 
               
               
                 229  
                 OIL 
               
               
                 230  
                 163-5 
               
               
                 231  
                 65-70 
               
               
                 232  
                 186-91 
               
               
                 233  
                 85-90 
               
               
                 234  
                 65-70 
               
               
                 235  
                 63-7 
               
               
                 236  
                 56-8 
               
               
                 237  
                 141-2 
               
               
                 238  
                 143-5 
               
               
                 239  
                 162-4 
               
               
                 240  
                 72-6 
               
               
                 241  
                 67-70 
               
               
                 242  
                 163-5 
               
               
                 243  
                 51-55 
               
               
                 244  
                 OIL 
               
               
                 245  
                 OIL 
               
               
                 246  
                 45-9 
               
               
                 247  
                 35-8 
               
               
                 248  
                 67-71 
               
               
                 249  
                 84-9 
               
               
                 250  
                 65-68 
               
               
                 251  
                 55-7 
               
               
                 252  
                 OIL 
               
               
                 253  
                 GLASS 
               
               
                 254  
                 71-5 
               
               
                 255  
                 134-8 
               
               
                 256  
                 145-7 
               
               
                 257  
                 OIL 
               
               
                 258  
                 232-40 
               
               
                 259  
                 165-9 
               
               
                 260  
                 55-8 
               
               
                 261  
                 65-7 
               
               
                 262  
                 75-7 
               
               
                 263  
                 &gt;50 
               
               
                 264  
                 155-7 
               
               
                 265  
                 130-6 
               
               
                 266  
                 258-61 
               
               
                 267  
                 110-8 
               
               
                 268  
                 73-7 
               
               
                 269  
                 270-5 
               
               
                 270  
                 265-72 
               
               
                 271  
                 62-72 
               
               
                 272  
                 OIL 
               
               
                 273  
                 220-2.5 
               
               
                 274  
                 116 SOFTENS 
               
               
                 275  
                 OIL 
               
               
                 276  
                 145-53 
               
               
                 277  
                 179-82 
               
               
                 278  
                 189-92 
               
               
                 279  
                 197-8 
               
               
                 280  
                 215-6 
               
               
                 362  
                 152-8 
               
               
                 363  
                 &gt;165 
               
               
                 364  
                 SOLID 
               
               
                 365  
                 172-7 
               
               
                 366  
                 130 
               
               
                 367  
                 150-5 
               
               
                 368  
                 87-93 
               
               
                 369  
                 125-30 
               
               
                 370  
                 130 
               
               
                 371  
                 SOLID 
               
               
                 372  
                 SOLID 
               
               
                 373  
                 160 
               
               
                 374  
                 190 
               
               
                 375  
                 &gt;200 
               
               
                 376  
                 142-8 
               
               
                 377  
                 122-30 
               
               
                 378  
                 200 C&gt; 
               
               
                 379  
                 116-22 
               
               
                 380  
                 201-4 
               
               
                 381  
                 117-24 
               
               
                 382  
                 193-5 
               
               
                 383  
                 131-40 
               
               
                 384  
                 103-5 
               
               
                 385  
                 158-160 
               
               
                 386  
                 132-5 
               
               
                 387  
                 112-4 
               
               
                 388  
                 107-9 
               
               
                 399  
                 177.5-8.5 
               
               
                 405  
                 130 
               
               
                 469  
                 98-100 
               
               
                 481  
                 SOLID 
               
               
                 493  
                 187-8 
               
               
                 500  
                 208-10 
               
               
                 513  
                 178-181 
               
               
                 522  
                 78-80 
               
               
                 527  
                 152-154 
               
               
                 563  
                 165-166 
               
               
                 595  
                 &gt;240 
               
               
                 618  
                 235-237.5 
               
               
                 693  
                 60-65 
               
               
                 694  
                 221.5-223 
               
               
                 695  
                 160-162 
               
               
                 696  
                 173-177 
               
               
                 697  
                 60-63 
               
               
                 698  
                 142-145.5 
               
               
                 699  
                 95-102 
               
               
                 700  
                 160-162 
               
               
                 701  
                 245-248 
               
               
                 702  
                 258-260 
               
               
                 705  
                 102-103 
               
               
                 706  
                 88-89 
               
               
                 708  
                 140 DEC 
               
               
                 709  
                 &gt;200 
               
               
                 710  
                 130 RESIN 
               
               
                 711  
                 &gt;200 
               
               
                 712  
                 93-98 RESIN 
               
               
                 713  
                 123-130 RESIN 
               
               
                 714  
                 160-165 RESIN 
               
               
                 715  
                 90-95 
               
               
                 716  
                 115-120 RESIN 
               
               
                 717  
                 120-125 
               
               
                 718  
                 110-116 
               
               
                 719  
                 120-125 
               
               
                 720  
                 128-132 RESIN 
               
               
                 721  
                 145-150 
               
               
                 722  
                 117-122 RESIN 
               
               
                 723  
                 107-112 RESIN 
               
               
                 724  
                 108-114 RESIN 
               
               
                 725  
                 135-140 RESIN 
               
               
                 726  
                 &gt;210 
               
               
                 727  
                 182-183 
               
               
                 728  
                 174-175 
               
               
                 729  
                 &gt;205 
               
               
                 730  
                 &gt;205 
               
               
                 731  
                 150-152 RESIN 
               
               
                 732  
                 195-200 
               
               
                 733  
                 &gt;205 
               
               
                 734  
                 SOLID 
               
               
                 735  
                 118-121 RESIN 
               
               
                 736  
                 88-92 
               
               
                 737  
                 &gt;200 
               
               
                 738  
                 133-135 
               
               
                 739  
                 130-132 
               
               
                 740  
                 178-180 
               
               
                 741  
                 118-121 RESIN 
               
               
                 742  
                 150-155 
               
               
                 743  
                 SOLID 
               
               
                 744  
                 160-162 
               
               
                 745  
                 &gt;200 
               
               
                 746  
                 106-109 
               
               
                 747  
                 98-100 
               
               
                 748  
                 104-110 RESIN 
               
               
                 749  
                 155-158 RESIN 
               
               
                 750  
                 137-139 
               
               
                 751  
                 189-190 
               
               
                 752  
                 78-82 
               
               
                 753  
                 87-89 
               
               
                 754  
                 75-77 
               
               
                 755  
                 96-98 
               
               
                 756  
                 90-92 
               
               
                 757  
                 60-62 
               
               
                 758  
                 95-97 
               
               
                 759  
                 144-146 
               
               
                 760  
                 146-147 
               
               
                 761  
                 70-76 
               
               
                 762  
                 185-187 
               
               
                 763  
                 63-65 
               
               
                 764  
                 OIL 
               
               
                 765  
                 50-54 
               
               
                 766  
                 172-173 
               
               
                 767  
                 239-241 
               
               
                   
               
             
          
         
       
     
     Biological Testing 
     The benzofused heterocyclic compounds of this invention were tested for pre- and postemergence herbicidal activity using a variety of crops and weeds. The test plants included soybean ( Glycine max  var. Winchester), field corn ( Zea mays  var. Pioneer 3732), wheat ( Triticum aestivum  var. Lew), morningglory ( Ipomea lacunosa  or  Ipomea hederacea ), velvetleaf ( Abutilon theophrasti ), green foxtail ( Setaria viridis ), Johnsongrass ( Sorghum halepense ), blackgrass ( Aloepecurus myosuroides ), common chickweed ( Stellaria media ), and common cocklebur ( Xanthium strumarium  L.). 
     For preemergence testing, two disposable fiber flats (8 cm×15 cm×25 cm) for each rate of application of each candidate herbicide were filled to an approximate depth of 6.5 cm with steam-sterilized sandy loam soil. The soil was leveled and impressed with a template to provide five evenly spaced furrows 13 cm long and 0.5 cm deep in each flat. Seeds of soybean, wheat, corn, green foxtail, and johnsongrass were planted in the furrows of the first flat, and seeds of velvetleaf, morningglory, common chickweed, cocklebur, and blackgrass were planted in the furrows of the second flat. The five-row template was employed to firmly press the seeds into place. A topping soil of equal portions of sand and sandy loam soil was placed uniformly on top of each flat to a depth of approximately 0.5 cm. Flats for postemergence testing were prepared in the same manner except that they were planted 9-14 days prior to the preemergence flats and were placed in a greenhouse and watered, thus allowing the seeds to germinate and the foliage to develop. 
     In both pre- and postemergence tests, a stock solution of the candidate herbicide was prepared by dissolving 0.27 g of the compound in 20 mL of water/acetone (50/50) containing 0.5% v/v sorbitan monolaurate. For an application rate of 3000 g/ha of herbicide a 10 mL portion of the stock solution was diluted with water/acetone (50/50) to 45 mL. The volumes of stock solution and diluent used to prepare solutions for lower application rates are shown in the following table: 
     
       
         
               
               
               
               
             
               
               
               
               
             
           
               
                   
               
               
                 Application 
                 Volume of 
                 Volume of 
                 Total Volume 
               
               
                 Rate 
                 Stock Solution 
                 Acetone/Water 
                 of Spray Solution 
               
               
                 (g/ha) 
                 (mL) 
                 (mL) 
                 (mL) 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 3000 
                 10 
                 35 
                 45 
               
               
                 1000 
                 3 
                 42 
                 45 
               
               
                 300 
                 1 
                 44 
                 45 
               
               
                 100 
                 0.3 
                 45 
                 45.3 
               
               
                 30 
                 0.1 
                 45 
                 45.1 
               
               
                 10 
                 0.03 
                 45 
                 45.03 
               
               
                 3 
                 0.01 
                 45 
                 45.01 
               
               
                   
               
             
          
         
       
     
     The preemergence flats were initially subjected to a light water spray. The four flats were placed two by two along a conveyor belt (i.e., the two preemergence followed by the two postemergence flats). The conveyor belt fed under a spray nozzle mounted about ten inches above the post-emergent foliage. The preemergent flats were elevated on the belt so that the soil surface was at the same level below the spray nozzle as the foliage canopy of the postemergent plants. The spray of herbicidal solution was commenced and once stabilized, the flats were passed under the spray at a speed to receive a coverage equivalent of 100 L/ha. At this coverage the application rates are those shown in the above table for the individual herbicidal solutions. The preemergence flats were watered immediately thereafter, placed in the greenhouse and watered regularly at the soil surface. The postemergence flats were immediately placed in the green-house and not watered until 24 hours after treatment with the test solution. Thereafter they were regularly watered at ground level. After 12-17 days the plants were examined and the phytotoxicity data were recorded. 
     Herbicidal activity data at selected application rates are given for various compounds of this invention in Table 4 and Table 5. The test compounds are identified by numbers which correspond to those in Tables 1 and 2. 
     Phytotoxicity data were taken as percent control. Percent control was determined by a method similar to the 0 to 100 rating system disclosed in “Research Methods in Weed Science,” 2nd ed., B. Truelove, Ed.; Southern Weed Science Society; Auburn University, Auburn, Ala., 1977. The rating system is as follows: 
     
       
         
               
             
               
               
               
               
             
           
               
                   
               
               
                 Herbicide Rating System 
               
             
          
           
               
                 Rating 
                 Description 
                   
                   
               
               
                 Percent 
                 of Main 
                 Crop 
                 Weed 
               
               
                 Control 
                 Categories 
                 Description 
                 Description 
               
               
                   
               
               
                  0 
                 No effect 
                 No crop 
                 No weed 
               
               
                   
                   
                 reduction/injury 
                 control 
               
               
                 10 
                 Slight 
                 Slight dis- 
                 Very poor weed 
               
               
                   
                 effect 
                 coloration or stunting 
                 control 
               
               
                 20 
                   
                 Some discoloration, 
                 Poor weed 
               
               
                   
                   
                 stunting or 
                 control 
               
               
                   
                   
                 stand loss 
               
               
                 30 
                   
                 Crop injury 
                 Poor to deficient 
               
               
                   
                   
                 more pronounced 
                 weed control 
               
               
                   
                   
                 but not lasting 
               
               
                 40 
                 Moderate 
                 Moderate injury, 
                 Deficient weed 
               
               
                   
                 effect 
                 crop usually recovers 
                 control 
               
               
                 50 
                   
                 Crop injury 
                 Deficient to 
               
               
                   
                   
                 more lasting, 
                 moderate weed 
               
               
                   
                   
                 recovery doubtful 
                 control 
               
               
                 60 
                   
                 Lasting crop 
                 Moderate weed 
               
               
                   
                   
                 injury, no recovery 
                 control 
               
               
                 70 
                 Severe 
                 Heavy injury and 
                 Control some- 
               
               
                   
                   
                 stand loss 
                 what less than 
               
               
                   
                   
                 satisfactory 
               
               
                 80 
                   
                 Crop nearly destroyed 
                 Satisfactory to 
               
               
                   
                   
                 a few survivors 
                 weed control 
               
               
                 90 
                   
                 Only occasional 
                 Very good to 
               
               
                   
                   
                 live plants left 
                 excellent control 
               
               
                 100  
                 Complete 
                 Complete crop 
                 Complete weed 
               
               
                   
                 effect 
                 destruction 
                 destruction 
               
               
                   
               
             
          
         
       
     
     Formulation 
     Compounds of the present invention were tested in the laboratory as water/acetone (50/50) solutions containing 0.5% v/v sorbitan monolaurate emulsifier. It is expected that all formulations normally employed in applications of herbicides would be usable with the compounds of the present invention. These include wettable powders, emulsifiable concentrates, water suspensions, flowable concentrates, and the like. 
     
       
         
               
             
               
               
               
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 4 
               
             
             
               
                   
               
               
                 PREEMERGENCE HERBICIDAL ACTIVITY (% CONTROL) 
               
             
          
           
               
                 No. 
                 SOY 
                 WHT 
                 CRN 
                 ABUTH 
                 IPOSS 
                 STEME 
                 XANPE 
                 ALOMY 
                 SETVI 
                 SORHA 
               
               
                   
               
               
                 1 
                 100 
                 85 
                 90 
                 100 
                 100 
                 100 
                 100 
                 90 
                 100 
                 95 
               
               
                 16 
                 100 
                 70 
                 90 
                 100 
                 100 
                 100 
                 90 
                 80 
                 100 
                 95 
               
               
                 25 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 95 
                 90 
                 100 
                 100 
               
               
                 26 
                 100 
                 90 
                 90 
                 100 
                 100 
                 100 
                 100 
                 95 
                 100 
                 100 
               
               
                 28 
                 100 
                 100 
                 95 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 30 
                 100 
                 100 
                 95 
                 100 
                 100 
                 100 
                 90 
                 100 
                 100 
                 100 
               
               
                 38 
                 60 
                 50 
                 80 
                 100 
                 100 
                 0 
                 70 
                 30 
                 75 
                 60 
               
               
                 42 
                 0 
                 10 
                 0 
                 100 
                 60 
                 30 
                 20 
                 50 
                 30 
                 0 
               
               
                 43 
                 50 
                 40 
                 80 
                 100 
                 100 
                 10 
                 — 
                 60 
                 70 
                 80 
               
               
                 49 
                 95 
                 50 
                 80 
                 100 
                 100 
                 20 
                 90 
                 — 
                 100 
                 90 
               
               
                 96 
                 100 
                 90 
                 95 
                 100 
                 100 
                 100 
                 — 
                 90 
                 100 
                 95 
               
               
                 98 
                 50 
                 40 
                 80 
                 80 
                 75 
                 70 
                 60 
                 10 
                 30 
                 65 
               
               
                 99 
                 40 
                 50 
                 60 
                 100 
                 100 
                 100 
                 — 
                 60 
                 100 
                 65 
               
               
                 100 
                 40 
                 30 
                 80 
                 100 
                 100 
                 20 
                 — 
                 60 
                 50 
                 70 
               
               
                 101 
                 80 
                 70 
                 100 
                 100 
                 100 
                 — 
                 80 
                 80 
                 100 
                 100 
               
               
                 102 
                 20 
                 30 
                 10 
                 100 
                 70 
                 — 
                 50 
                 90 
                 100 
                 60 
               
               
                 103 
                 50 
                 50 
                 80 
                 100 
                 100 
                 — 
                 70 
                 90 
                 100 
                 70 
               
               
                 104 
                 100 
                 100 
                 100 
                 100 
                 100 
                 — 
                 100 
                 100 
                 100 
                 100 
               
               
                 106 
                 30 
                 40 
                 70 
                 100 
                 100 
                 95 
                 60 
                 70 
                 90 
                 55 
               
               
                 107 
                 80 
                 60 
                 90 
                 100 
                 100 
                 100 
                 40 
                 75 
                 100 
                 100 
               
               
                 108 
                 0 
                 0 
                 10 
                 70 
                 50 
                 40 
                 10 
                 50 
                 50 
                 30 
               
               
                 109 
                 100 
                 100 
                 90 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 110 
                 100 
                 50 
                 70 
                 100 
                 90 
                 100 
                 40 
                 80 
                 100 
                 100 
               
               
                 112 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 221 
                 70 
                 60 
                 85 
                 100 
                 100 
                 80 
                 ND 
                 ND 
                 100 
                 95 
               
               
                 222 
                 100 
                 70 
                 90 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
               
               
                 223 
                 100 
                 50 
                 80 
                 100 
                 100 
                 100 
                 90 
                 ND 
                 100 
                 100 
               
               
                 224 
                 100 
                 80 
                 90 
                 100 
                 100 
                 100 
                 95 
                 80 
                 100 
                 100 
               
               
                 225 
                 40 
                 20 
                 30 
                 90 
                 50 
                 70 
                 50 
                 ND 
                 100 
                 60 
               
               
                 226 
                 70 
                 50 
                 70 
                 100 
                 90 
                 90 
                 60 
                 ND 
                 100 
                 80 
               
               
                 227 
                 100 
                 80 
                 90 
                 100 
                 100 
                 100 
                 ND 
                 95 
                 100 
                 100 
               
               
                 228 
                 100 
                 80 
                 95 
                 100 
                 100 
                 100 
                 90 
                 ND 
                 100 
                 100 
               
               
                 229 
                 100 
                 70 
                 90 
                 100 
                 100 
                 100 
                 95 
                 80 
                 100 
                 100 
               
               
                 230 
                 100 
                 40 
                 80 
                 100 
                 100 
                 100 
                 100 
                 80 
                 100 
                 100 
               
               
                 231 
                 100 
                 80 
                 100 
                 100 
                 100 
                 100 
                 100 
                 90 
                 100 
                 100 
               
               
                 232 
                 20 
                 30 
                 50 
                 90 
                 80 
                 20 
                 10 
                 ND 
                 40 
                 25 
               
               
                 233 
                 40 
                 30 
                 70 
                 100 
                 95 
                 20 
                 20 
                 ND 
                 60 
                 50 
               
               
                 234 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 80 
                 100 
                 100 
               
               
                 235 
                 100 
                 90 
                 100 
                 100 
                 100 
                 100 
                 100 
                 80 
                 100 
                 100 
               
               
                 236 
                 100 
                 70 
                 95 
                 100 
                 100 
                 100 
                 100 
                 80 
                 100 
                 100 
               
               
                 237 
                 100 
                 90 
                 90 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 238 
                 100 
                 60 
                 70 
                 100 
                 100 
                 60 
                 80 
                 50 
                 90 
                 90 
               
               
                 239 
                 100 
                 70 
                 90 
                 100 
                 100 
                 100 
                 ND 
                 ND 
                 100 
                 90 
               
               
                 240 
                 100 
                 95 
                 95 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
               
               
                 241 
                 60 
                 70 
                 95 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
               
               
                 242 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 243 
                 100 
                 80 
                 95 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
               
               
                 244 
                 95 
                 80 
                 100 
                 100 
                 90 
                 70 
                 100 
                 70 
                 100 
                 100 
               
               
                 245 
                 100 
                 60 
                 80 
                 100 
                 100 
                 90 
                 100 
                 70 
                 100 
                 80 
               
               
                 246 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 247 
                 100 
                 90 
                 90 
                 100 
                 100 
                 95 
                 100 
                 85 
                 100 
                 100 
               
               
                 248 
                 100 
                 90 
                 95 
                 100 
                 100 
                 100 
                 100 
                 95 
                 100 
                 100 
               
               
                 249 
                 100 
                 80 
                 95 
                 100 
                 100 
                 100 
                 90 
                 80 
                 10 
                 100 
               
               
                 250 
                 80 
                 40 
                 50 
                 100 
                 100 
                 ND 
                 100 
                 60 
                 100 
                 70 
               
               
                 251 
                 90 
                 90 
                 95 
                 100 
                 100 
                 95 
                 100 
                 90 
                 100 
                 100 
               
               
                 252 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
                 100 
               
               
                 253 
                 100 
                 95 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 ND 
                 100 
                 100 
               
               
                 254 
                 25 
                 20 
                 80 
                 100 
                 50 
                 30 
                 50 
                 60 
                 100 
                 80 
               
               
                 255 
                 100 
                 90 
                 95 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
               
               
                 256 
                 100 
                 80 
                 95 
                 100 
                 100 
                 100 
                 ND 
                 70 
                 100 
                 90 
               
               
                 257 
                 40 
                 0 
                 10 
                 90 
                 70 
                 0 
                 20 
                 20 
                 70 
                 10 
               
               
                 258 
                 30 
                 30 
                 75 
                 100 
                 60 
                 0 
                 60 
                 ND 
                 40 
                 40 
               
               
                 259 
                 70 
                 40 
                 80 
                 100 
                 70 
                 100 
                 55 
                 ND 
                 100 
                 95 
               
               
                 260 
                 100 
                 70 
                 80 
                 100 
                 100 
                 100 
                 100 
                 95 
                 100 
                 100 
               
               
                 261 
                 100 
                 80 
                 95 
                 100 
                 100 
                 100 
                 90 
                 80 
                 100 
                 100 
               
               
                 262 
                 90 
                 40 
                 40 
                 100 
                 100 
                 100 
                 100 
                 50 
                 100 
                 70 
               
               
                 263 
                 100 
                 50 
                 65 
                 100 
                 100 
                 100 
                 95 
                 75 
                 100 
                 70 
               
               
                 264 
                 0 
                 0 
                 10 
                 20 
                 0 
                 20 
                 30 
                 0 
                 10 
                 10 
               
               
                 265 
                 70 
                 40 
                 80 
                 90 
                 100 
                 20 
                 70 
                 ND 
                 80 
                 60 
               
               
                 266 
                 50 
                 30 
                 60 
                 40 
                 70 
                 0 
                 0 
                 ND 
                 30 
                 30 
               
               
                 267 
                 0 
                 10 
                 20 
                 10 
                 10 
                 0 
                 50 
                 50 
                 5 
                 0 
               
               
                 268 
                 30 
                 30 
                 50 
                 100 
                 95 
                 20 
                 0 
                 ND 
                 60 
                 60 
               
               
                 269 
                 60 
                 30 
                 80 
                 100 
                 100 
                 100 
                 100 
                 70 
                 100 
                 75 
               
               
                 270 
                 70 
                 70 
                 90 
                 100 
                 100 
                 ND 
                 60 
                 65 
                 100 
                 100 
               
               
                 271 
                 80 
                 70 
                 90 
                 100 
                 100 
                 100 
                 100 
                 80 
                 100 
                 90 
               
               
                 272 
                 20 
                 0 
                 20 
                 100 
                 70 
                 100 
                 20 
                 70 
                 90 
                 60 
               
               
                 273 
                 100 
                 80 
                 90 
                 100 
                 100 
                 100 
                 100 
                 90 
                 100 
                 100 
               
               
                 274 
                 100 
                 100 
                 90 
                 100 
                 100 
                 90 
                 100 
                 95 
                 100 
                 100 
               
               
                 275 
                 100 
                 80 
                 100 
                 100 
                 100 
                 100 
                 100 
                 80 
                 100 
                 95 
               
               
                 362 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 363 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 364 
                 100 
                 60 
                 80 
                 100 
                 100 
                 100 
                 100 
                 80 
                 100 
                 80 
               
               
                 365 
                 ND 
                 30 
                 30 
                 100 
                 100 
                 100 
                 100 
                 60 
                 75 
                 60 
               
               
                 366 
                 10 
                 10 
                 0 
                 70 
                 20 
                 0 
                 10 
                 0 
                 50 
                 40 
               
               
                 367 
                 100 
                 95 
                 100 
                 100 
                 100 
                 100 
                 100 
                 90 
                 100 
                 100 
               
               
                 368 
                 100 
                 100 
                 95 
                 100 
                 100 
                 100 
                 100 
                 95 
                 100 
                 100 
               
               
                 369 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 370 
                 100 
                 100 
                 95 
                 100 
                 100 
                 100 
                 100 
                 90 
                 100 
                 100 
               
               
                 371 
                 100 
                 95 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 372 
                 100 
                 90 
                 95 
                 100 
                 100 
                 100 
                 100 
                 80 
                 100 
                 80 
               
               
                 373 
                 100 
                 70 
                 90 
                 100 
                 100 
                 100 
                 100 
                 70 
                 100 
                 90 
               
               
                 374 
                 30 
                 0 
                 10 
                 100 
                 95 
                 90 
                 80 
                 40 
                 100 
                 75 
               
               
                 375 
                 80 
                 30 
                 90 
                 100 
                 80 
                 95 
                 80 
                 80 
                 100 
                 95 
               
               
                 376 
                 50 
                 60 
                 80 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 70 
               
               
                 377 
                 100 
                 70 
                 90 
                 100 
                 100 
                 ND 
                 100 
                 100 
                 100 
                 100 
               
               
                 378 
                 90 
                 70 
                 90 
                 100 
                 100 
                 100 
                 100 
                 80 
                 100 
                 95 
               
               
                 379 
                 100 
                 50 
                 70 
                 100 
                 100 
                 ND 
                 100 
                 80 
                 100 
                 95 
               
               
                 380 
                 80 
                 35 
                 20 
                 100 
                 100 
                 ND 
                 80 
                 90 
                 100 
                 70 
               
               
                 381 
                 100 
                 40 
                 80 
                 100 
                 100 
                 ND 
                 100 
                 90 
                 100 
                 80 
               
               
                 382 
                 60 
                 45 
                 30 
                 100 
                 70 
                 ND 
                 60 
                 90 
                 95 
                 80 
               
               
                 383 
                 80 
                 40 
                 20 
                 100 
                 60 
                 ND 
                 70 
                 80 
                 75 
                 55 
               
               
                 399 
                 95 
                 80 
                 95 
                 100 
                 95 
                 100 
                 70 
                 60 
                 100 
                 0 
               
               
                 493 
                 80 
                 70 
                 90 
                 100 
                 100 
                 100 
                 70 
                 75 
                 100 
                 100 
               
               
                 500 
                 95 
                 75 
                 90 
                 100 
                 100 
                 100 
                 100 
                 75 
                 100 
                 100 
               
               
                 522 
                 90 
                 40 
                 80 
                 100 
                 100 
                 100 
                 50 
                 75 
                 100 
                 100 
               
               
                 595 
                 10 
                 0 
                 0 
                 60 
                 50 
                 10 
                 20 
                 ND 
                 0 
                 40 
               
               
                   
               
               
                 Rate of Application is 0.3 Kg/Ha. SOY is soybean; WHT is wheat; CRN is corn; ABUTH is velvetleaf; IPOSS is morningglory; STEME is chickweed; XANPE is cocklebur; ALOMY is blackgrass; SETVI is green foxtail; SORHA is johnsongrass  
               
             
          
         
       
     
     
       
         
               
             
               
               
               
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 5 
               
             
             
               
                   
               
               
                 POSTEMERGENCE HERBICIDAL ACTIVITY (% CONTROL) 
               
             
          
           
               
                 No. 
                 SOY 
                 WHT 
                 CRN 
                 ABUTH 
                 IPOSS 
                 STEME 
                 XANPE 
                 ALOMY 
                 SETVI 
                 SORHA 
               
               
                   
               
               
                 1 
                 95 
                 65 
                 80 
                 100 
                 100 
                 90 
                 100 
                 70 
                 80 
                 80 
               
               
                 16 
                 95 
                 60 
                 80 
                 100 
                 100 
                 70 
                 95 
                 70 
                 80 
                 80 
               
               
                 25 
                 100 
                 80 
                 90 
                 100 
                 100 
                 100 
                 100 
                 80 
                 100 
                 90 
               
               
                 26 
                 96 
                 60 
                 80 
                 100 
                 100 
                 80 
                 100 
                 80 
                 100 
                 80 
               
               
                 28 
                 100 
                 80 
                 80 
                 100 
                 100 
                 100 
                 90 
                 100 
                 100 
                 95 
               
               
                 30 
                 95 
                 80 
                 90 
                 100 
                 100 
                 100 
                 100 
                 90 
                 100 
                 100 
               
               
                 38 
                 70 
                 35 
                 60 
                 100 
                 100 
                 0 
                 45 
                 20 
                 40 
                 50 
               
               
                 42 
                 65 
                 30 
                 60 
                 90 
                 60 
                 — 
                 50 
                 40 
                 100 
                 20 
               
               
                 43 
                 80 
                 30 
                 70 
                 100 
                 100 
                 70 
                 50 
                 — 
                 50 
                 50 
               
               
                 49 
                 95 
                 70 
                 80 
                 100 
                 100 
                 40 
                 30 
                 — 
                 100 
                 90 
               
               
                 96 
                 100 
                 90 
                 90 
                 100 
                 100 
                 100 
                 100 
                 — 
                 100 
                 100 
               
               
                 98 
                 40 
                 10 
                 50 
                 60 
                 20 
                 5 
                 20 
                 5 
                 40 
                 20 
               
               
                 99 
                 80 
                 40 
                 80 
                 100 
                 100 
                 95 
                 70 
                 — 
                 70 
                 65 
               
               
                 100 
                 85 
                 40 
                 60 
                 90 
                 100 
                 50 
                 50 
                 — 
                 30 
                 40 
               
               
                 101 
                 95 
                 50 
                 80 
                 100 
                 100 
                 — 
                 — 
                 60 
                 65 
                 65 
               
               
                 102 
                 80 
                 30 
                 75 
                 100 
                 100 
                 — 
                 — 
                 60 
                 90 
                 60 
               
               
                 103 
                 90 
                 50 
                 80 
                 100 
                 80 
                 — 
                 80 
                 70 
                 100 
                 60 
               
               
                 104 
                 100 
                 100 
                 100 
                 100 
                 100 
                 — 
                 — 
                 — 
                 100 
                 100 
               
               
                 106 
                 80 
                 30 
                 75 
                 100 
                 100 
                 — 
                 — 
                 60 
                 100 
                 70 
               
               
                 107 
                 95 
                 40 
                 100 
                 100 
                 100 
                 100 
                 — 
                 90 
                 100 
                 100 
               
               
                 108 
                 50 
                 20 
                 60 
                 20 
                 60 
                 0 
                 10 
                 10 
                 70 
                 20 
               
               
                 109 
                 90 
                 90 
                 80 
                 100 
                 100 
                 — 
                 100 
                 90 
                 100 
                 90 
               
               
                 110 
                 80 
                 40 
                 50 
                 100 
                 100 
                 — 
                 100 
                 70 
                 80 
                 70 
               
               
                 112 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 221 
                 95 
                 50 
                 60 
                 100 
                 100 
                 100 
                 60 
                 40 
                 70 
                 70 
               
               
                 222 
                 100 
                 70 
                 90 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 223 
                 95 
                 40 
                 90 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
               
               
                 224 
                 95 
                 70 
                 100 
                 100 
                 100 
                 100 
                 100 
                 90 
                 100 
                 ND 
               
               
                 225 
                 60 
                 30 
                 60 
                 100 
                 75 
                 ND 
                 70 
                 ND 
                 90 
                 60 
               
               
                 226 
                 70 
                 40 
                 80 
                 100 
                 95 
                 80 
                 90 
                 ND 
                 100 
                 80 
               
               
                 227 
                 95 
                 60 
                 90 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 228 
                 90 
                 50 
                 80 
                 100 
                 100 
                 80 
                 95 
                 ND 
                 100 
                 90 
               
               
                 229 
                 95 
                 60 
                 80 
                 100 
                 100 
                 100 
                 100 
                 70 
                 100 
                 100 
               
               
                 230 
                 95 
                 40 
                 80 
                 100 
                 100 
                 90 
                 100 
                 70 
                 100 
                 90 
               
               
                 231 
                 100 
                 70 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
                 100 
               
               
                 232 
                 75 
                 50 
                 30 
                 100 
                 80 
                 20 
                 40 
                 ND 
                 30 
                 10 
               
               
                 233 
                 90 
                 30 
                 60 
                 100 
                 100 
                 30 
                 30 
                 ND 
                 30 
                 30 
               
               
                 234 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 235 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 236 
                 100 
                 75 
                 90 
                 100 
                 100 
                 100 
                 100 
                 80 
                 100 
                 100 
               
               
                 237 
                 100 
                 95 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
                 100 
                 100 
               
               
                 238 
                 80 
                 30 
                 70 
                 100 
                 100 
                 ND 
                 100 
                 40 
                 80 
                 70 
               
               
                 239 
                 95 
                 60 
                 80 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 80 
               
               
                 240 
                 95 
                 95 
                 100 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
               
               
                 241 
                 90 
                 60 
                 70 
                 100 
                 100 
                 85 
                 95 
                 ND 
                 100 
                 70 
               
               
                 242 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 243 
                 95 
                 70 
                 95 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
               
               
                 244 
                 95 
                 60 
                 90 
                 100 
                 100 
                 100 
                 100 
                 75 
                 100 
                 ND 
               
               
                 245 
                 85 
                 40 
                 75 
                 100 
                 100 
                 60 
                 70 
                 50 
                 70 
                 70 
               
               
                 246 
                 95 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
               
               
                 247 
                 95 
                 80 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 ND 
               
               
                 248 
                 80 
                 50 
                 95 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
               
               
                 249 
                 95 
                 80 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 ND 
               
               
                 250 
                 95 
                 50 
                 80 
                 100 
                 100 
                 80 
                 100 
                 40 
                 100 
                 100 
               
               
                 251 
                 95 
                 70 
                 90 
                 100 
                 100 
                 100 
                 95 
                 100 
                 100 
                 95 
               
               
                 252 
                 95 
                 90 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
                 100 
               
               
                 253 
                 95 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
               
               
                 254 
                 95 
                 40 
                 80 
                 100 
                 70 
                 ND 
                 95 
                 50 
                 100 
                 80 
               
               
                 255 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
               
               
                 256 
                 100 
                 80 
                 90 
                 100 
                 100 
                 100 
                 100 
                 80 
                 100 
                 100 
               
               
                 257 
                 70 
                 20 
                 70 
                 100 
                 60 
                 30 
                 70 
                 30 
                 70 
                 50 
               
               
                 258 
                 80 
                 30 
                 60 
                 80 
                 70 
                 5 
                 50 
                 30 
                 60 
                 50 
               
               
                 259 
                 80 
                 35 
                 75 
                 100 
                 90 
                 30 
                 70 
                 55 
                 80 
                 70 
               
               
                 260 
                 90 
                 80 
                 70 
                 100 
                 100 
                 ND 
                 100 
                 90 
                 100 
                 90 
               
               
                 261 
                 95 
                 80 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 262 
                 95 
                 60 
                 80 
                 100 
                 100 
                 95 
                 95 
                 50 
                 100 
                 80 
               
               
                 263 
                 95 
                 80 
                 90 
                 100 
                 100 
                 100 
                 100 
                 60 
                 90 
                 70 
               
               
                 264 
                 50 
                 20 
                 50 
                 40 
                 40 
                 0 
                 30 
                 0 
                 ND 
                 20 
               
               
                 265 
                 70 
                 40 
                 60 
                 100 
                 100 
                 30 
                 20 
                 ND 
                 40 
                 20 
               
               
                 266 
                 60 
                 40 
                 60 
                 50 
                 60 
                 10 
                 10 
                 ND 
                 40 
                 40 
               
               
                 267 
                 50 
                 15 
                 50 
                 80 
                 40 
                 10 
                 10 
                 20 
                 30 
                 20 
               
               
                 268 
                 70 
                 40 
                 60 
                 50 
                 90 
                 20 
                 ND 
                 ND 
                 70 
                 40 
               
               
                 269 
                 90 
                 40 
                 70 
                 100 
                 80 
                 80 
                 ND 
                 ND 
                 70 
                 60 
               
               
                 270 
                 70 
                 40 
                 50 
                 100 
                 60 
                 40 
                 ND 
                 50 
                 50 
                 50 
               
               
                 271 
                 80 
                 40 
                 60 
                 100 
                 100 
                 100 
                 ND 
                 ND 
                 70 
                 50 
               
               
                 272 
                 50 
                 30 
                 45 
                 100 
                 60 
                 50 
                 50 
                 20 
                 70 
                 40 
               
               
                 273 
                 95 
                 60 
                 95 
                 100 
                 100 
                 90 
                 100 
                 80 
                 100 
                 100 
               
               
                 274 
                 95 
                 60 
                 95 
                 100 
                 100 
                 90 
                 100 
                 90 
                 100 
                 100 
               
               
                 275 
                 100 
                 70 
                 90 
                 100 
                 100 
                 100 
                 100 
                 95 
                 100 
                 100 
               
               
                 362 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
                 100 
               
               
                 363 
                 100 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
                 100 
                 100 
               
               
                 364 
                 95 
                 40 
                 80 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
               
               
                 365 
                 100 
                 40 
                 70 
                 100 
                 100 
                 100 
                 ND 
                 70 
                 80 
                 30 
               
               
                 366 
                 70 
                 30 
                 80 
                 95 
                 80 
                 30 
                 100 
                 30 
                 50 
                 50 
               
               
                 367 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 368 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 369 
                 100 
                 80 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
                 100 
                 100 
               
               
                 370 
                 100 
                 95 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 371 
                 95 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
               
               
                 372 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 373 
                 100 
                 80 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
                 100 
               
               
                 374 
                 80 
                 25 
                 30 
                 100 
                 95 
                 80 
                 100 
                 25 
                 80 
                 60 
               
               
                 375 
                 95 
                 40 
                 90 
                 100 
                 95 
                 100 
                 100 
                 90 
                 80 
                 100 
               
               
                 376 
                 90 
                 50 
                 95 
                 100 
                 100 
                 ND 
                 100 
                 90 
                 100 
                 100 
               
               
                 377 
                 95 
                 80 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 100 
                 100 
                 100 
               
               
                 378 
                 90 
                 40 
                 90 
                 100 
                 90 
                 ND 
                 100 
                 80 
                 100 
                 100 
               
               
                 379 
                 95 
                 80 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 70 
                 100 
                 100 
               
               
                 380 
                 95 
                 30 
                 95 
                 100 
                 100 
                 ND 
                 100 
                 70 
                 100 
                 80 
               
               
                 381 
                 95 
                 40 
                 95 
                 100 
                 100 
                 ND 
                 100 
                 100 
                 100 
                 100 
               
               
                 382 
                 80 
                 40 
                 100 
                 100 
                 100 
                 ND 
                 100 
                 80 
                 90 
                 80 
               
               
                 383 
                 95 
                 40 
                 95 
                 100 
                 95 
                 ND 
                 100 
                 60 
                 95 
                 70 
               
               
                 399 
                 95 
                 30 
                 70 
                 100 
                 100 
                 100 
                 100 
                 50 
                 70 
                 60 
               
               
                 493 
                 95 
                 60 
                 90 
                 100 
                 100 
                 80 
                 100 
                 65 
                 100 
                 100 
               
               
                 500 
                 95 
                 65 
                 95 
                 100 
                 100 
                 90 
                 100 
                 80 
                 100 
                 100 
               
               
                 522 
                 90 
                 45 
                 90 
                 100 
                 100 
                 100 
                 100 
                 50 
                 100 
                 100 
               
               
                 595 
                 50 
                 10 
                 60 
                 30 
                 40 
                 0 
                 20 
                 10 
                 20 
                 20 
               
               
                   
               
               
                 Rate of Application is 0.3 Kg/Ha. SOY is soybean; WHT is wheat; CRN is corn; ABUTH is velvetleaf; IPOSS is Morningglory; STEME is chickweed; XANPE is cocklebur; ALOMY is blackgrass; SETVI is green foxtail; SORHA is johnsongrass  
               
             
          
         
       
     
     Herbicidal compositions are prepared by combining herbicidally effective amounts of the active compounds with adjuvants and carriers normally employed in the art for facilitating the dispersion of activeingredients for the particular utility desired, recognizing the fact that the formulation and mode of application of a toxicant may affect the activity of the material in a given application. Thus, for agricultural use the present herbicidal compounds may be formulated as granules of relatively large particle size, as water-soluble or water-dispersible granules, as powdery dusts, as wettable powders, as emulsifiable concentrates, as solutions, or as any of several other known types of formulations, depending on the desired mode of application. It is to be understood that the amounts specified in this specification are intended to be approximate only, as if the word “about” were placed in front of the amounts specified. 
     These herbicidal compositions may be applied either as water-diluted sprays, or dusts, or granules to the areas in which suppression of vegetation is desired. These formulations may contain as little as 0.1%, 0.2% or 0.5% to as much as 95% or more by weight of active ingredient. 
     Dusts are free flowing admixtures of the active ingredient with finely divided solids such as talc, natural clays, kieselguhr, flours such as walnut shell and cottonseed flours, and other organic and inorganic solids which act as dispersants and carriers for the toxicant; these finely divided solids have an average particle size of less than about 50 microns. A typical dust formulation useful herein is one containing 1.0 part or less of the herbicidal compound and 99.0 parts of talc. 
     Wettable powders, also useful formulations for both pre- and post-emergence herbicides, are in the form of finely divided particles which disperse readily in water or other dispersant. The wettable powder is ultimately applied to the soil either as a dry dust or as an emulsion in water or other liquid. Typical carriers for wettable powders include Fuller&#39;s earth, kaolin clays, silicas, and other highly absorbent, readily wet inorganic diluents. Wettable powders normally are prepared to contain about 5-80% of active ingredient, depending on the absorbency of the carrier, and usually also contain a small amount of a wetting, dispersing or emulsifying agent to facilitate dispersion. For example, a useful wettable powder formulation contains 80.0 parts of the herbicidal compound, 17.9 parts of Palmetto clay, and 1.0 part of sodium lignosulfonate and 0.3 part of sulfonated aliphatic polyester as wetting agents. Additional wetting agent and/or oil will frequently be added to the tank mix for post-emergence application to facilitate dispersion on the foliage and absorption by the plant. 
     Other useful formulations for herbicidal applications are emulsifiable concentrates (ECs) which are homogeneous liquid compositions dispersible in water or other dispersant, and may consist entirely of the herbicidal compound and a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isphorone, or other non-volatile organic solvents. For herbicidal application these concentrates are dispersed in water or other liquid carrier and normally applied as a spray to the area to be treated. The percentage by weight of the essential active ingredient may vary according to the manner in which the composition is to be applied, but in general comprises 0.5 to 95% of active ingredient by weight of the herbicidal composition. 
     Flowable formulations are similar to ECs except that the active ingredient is suspended in a liquid carrier, generally water. Flowables, like ECs, may include a small amount of a surfactant, and will typically contain active ingredients in the range of 0.5 to 95%, frequently from 10 to 50%, by weight of the composition. For application, flowables may be diluted in water or other liquid vehicle, and are normally applied as a spray to the area to be treated. 
     Typical wetting, dispersing or emulsifying agents used in agricultural formulations include, but are not limited to, the alkyl and alkylaryl sulfonates and sulfates and their sodium salts; alkylaryl polyether alcohols; sulfated higher alcohols; polyethylene oxides; sulfonated animal and vegetable oils; sulfonated petroleum oils; fatty acid esters of polyhydric alcohols and the ethylene oxide addition products of such esters; and the addition product of long-chain mercaptans and ethylene oxide. Many other types of useful surface-active agents are available in commerce. Surface-active agents, when used, normally comprise 1 to 15% by weight of the composition. 
     Other useful formulations include suspensions of the active ingredient in a relatively non-volatile solvent such as water, corn oil, kerosene, propylene glycol, or other suitable solvents. 
     Still other useful formulations for herbicidal applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene, or other organic solvents. Granular formulations, wherein the toxicant is carried on relative coarse particles, are of particular utility for aerial distribution or for penetration of cover crop canopy. Pressurized sprays, typically aerosols wherein the active ingredient is dispersed in finely divided form as a result of vaporization of a low boiling dispersant solvent carrier, such as the Freon fluorinated hydrocarbons, may also be used. Water-soluble or water-dispersible granules are free-flowing, non-dusty, and readily water-soluble or water-miscible. The soluble or dispersible granular formulations described in U.S. Pat. No. 3,920,442 are useful herein with the present herbicidal compounds. In use by the farmer on the field, the granular formulations, emulsifiable concentrates, flowable concentrates, solutions, etc., may be diluted with water to give a concentration of active ingredient in the range of say 0.1% or 0.2% to 1.5% or 2%. 
     The active herbicidal compounds of this invention may be formulated and/or applied with insecticides, fungicides, nematicides, plant growth regulators, fertilizers, or other agricultural chemicals and may be used as effective soil sterilants as well as selective herbicides in agriculture. In applying an active compound of this invention, whether formulated alone or with other agricultural chemicals, an effective amount and concentration of the active compound is of course employed; the amount may be as low as, e.g. about 1 to 250 g/ha, preferably about 4 to 30 g/ha. For field use, where there are losses of herbicide, higher application rates (e.g., four times the rates mentioned above) may be employed. 
     The active herbicidal compounds of the present invention may also be used in combination with other herbicides. Such herbicides include, for example: N-(phosphonomethyl) glycine (“glyphosate”); aryloxyalkanoic acids such as (2,4-dichlorophenoxy)acetic acid (“2,4-D”), (4-chloro-2-methylphenoxy)acetic acid (“MCPA”), (+/−)-2-(4-chloro-2-methylphenoxy)propanoic acid (MCPP); ureas such as N,N-dimethyl-N′-[4-(1-methylethyl)phenyl]urea (“isoproturon”); imidazolinones such as 2-[4,5-dihydro4-methyl4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-pyridinecarboxylic acid (“imazapyr”), a reaction product comprising (+/−)-2-[4,5-dihydro4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]4-methylbenzoic acid and (+/−)-2-[4,5-dihydro4-methyl4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-methylbenzoic acid (“imazamethabenz”), (+/−)-2-[4,5-dihydro4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-ethyl-3-pyridinecarboxylic acid (“imazethapyr”), and (+/−)-2-[4,5-dihydro4-methyl4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-quinolinecarboxylic acid (“imazaquin”); diphenyl ethers such as 5-[2-chloro4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid (“acifluorfen”), methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate (“bifenox”), and 5-[2-chloro4-(trifluoro-methyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamide (“fomasafen”); hydroxybenzonitriles such as 4-hydroxy-3,5-diiodobenzonitrile (“ioxynil”) and 3,5-dibromo-4-hydroxybenzonitrile (“bromoxynil”); sulfonylureas such as 2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoic acid (“chlorimuron”), 2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide (“chlorsulfuron”), 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]benzoic acid (“bensulfuron”), 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-1-methyl-1H-pyrazol-4-carboxylic acid (“pyrazosulfuron”), 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-2-thiophenecarboxylic acid (“thifensulfuron”), and 2-(2-chloroethoxy)-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide (“triasulfuron”); 2-(4-aryloxyphenoxy)alkanoic acids such as (+/−)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]propanoic acid (“fenoxaprop”), (+/−)-2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid (“fluazifop”), (+/−)-2-[4-(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid (“quizalofop”), and (+/−)-2-[-(2,4-dichlorophenoxy)phenoxy]propanoic acid (“diclofop”); benzothiadiazinones such as 3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide (“bentazone”); 2-chloroacetanilides such as N-butoxymethyl)-2-chloro-2′,6′-diethylacetanilide (“butachlor”); 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide (“metachlor”), 2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide (“acetochlor”), and (RS)-2-chloro-N-(ethoxymethyl)-N-(2-methoxy-1-methylethyl)acetamide (“dimethenamide”); arenecarboxylic acids such as 3,6-dichloro-2-methoxybenzoic acid (“dicamba”); and pyridyloxyacetic acids such as [(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy]acetic acid (“fluroxypyr”). 
     It is apparent that various modifications may be made in the formulations and application of the compounds of the present invention without departing from the inventive concepts herein, as defined in the claims.