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: ##STR1## 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 claims the benefit of U.S. Provisional Application No. 60/039,172 filed 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: ##STR2## 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: ##STR3## where (1) A is nitrogen double-bonded to position 2 and B is oxygen; 
     (2) A is oxygen and B is CR 1  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 1  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.tbd.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 ##STR4##  and R 3  is selected from hydrogen, alkyl, haloalkyl, CH 2  CN, CH 2  CH═CH 2 , CH 2  C.tbd.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.tbd.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 ##STR5## 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 ##STR6## 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: ##STR7## 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 &#34;alkyl,&#34; &#34;alkenyl,&#34; &#34;alkynyl,&#34; &#34;haloalkyl,&#34; and &#34;alkoxy&#34; used alone or as part of a larger moiety, includes straight or branched carbon chains of 1 to 6 carbon atoms. &#34;Halogen&#34; refers to fluorine, bromine or chlorine. &#34;THF&#34; means tetrahydrofuran, &#34;DMF&#34; means N,N-dimethylformamide, and &#34;DBU&#34; means 1,8-diazabicyclo[5.4.0]undec-7-ene. When &#34;n&#34; in is 2 or 3, the substituents X may be the same or different from one another. 
     SCHEME 1 ##STR8## 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 , Nal, H 2  O; (g) BBr 3 , CH 2  Cl 2  ; (h) HC.tbd.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. 
     Scheme 2 ##STR9## 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&#39;-halide, Ag 2  O, CH 2  Cl 2  (to give 11 where R═R&#39;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. 
     Scheme 3 ##STR10## 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. ##STR11## 
     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). ##STR12## 
     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. 
     Scheme 4 ##STR13## 
     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. ##STR14## 
     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(1H,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-amino-4-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-Methoxy-Benzoxazol-4-yl-2,4(1H,3H)-Pyrimidinedione (Compound 109) 
     Step A 1-methyl-6-trifluoromethyl-3-(7-bromo-5-fluorobenzoxazol-2-on-4-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(l) 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)Benzoxazol-4-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-amino-4-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-amino-4-chloro-2-fluoro-5-hydroxy-phenyl)-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 1 M 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 3 N 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 12 M 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-amino-4-chloro-6-fluoro-2-methoxyphenyl)carbamate. The NMR spectrum was consistent with the proposed structure. 
     Step D 3-(3-amino-4-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-amino-4,4,4-trifluorocrotonate, 8.5 grams (0.032 mole) of ethyl N-(3-amino-4-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-amino-4-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-amino-4-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-amino-4-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(1 H,3H)-pyrimidinedione in 75 mL of methylene chloride was cooled in a dry ice/acetone bath and 22.0 mL (0.022 mole) of 1 M 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-diamino-4-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-amino-4-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-diamino-4-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-amino-4-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-diamino-4-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 3-4. 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-Butyl-4-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-diamino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, 15.0 mL of ethanol, and 4 mL of 5 M 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-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-amino-4-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 347-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 ##STR15##where A is nitrogen double bonded to position 2 and B is O; J is ##STR16##Compound No. X        R         R3______________________________________1            4-Cl, 6-F                 CH.sub.3  CH.sub.32            4-Cl, 6-F                 CH.sub.3  C.sub.2 H.sub.53            4-Cl, 6-F                 CH.sub.3  CH.sub.2 CN4            4-Cl, 6-F                 CH.sub.3  CH.sub.2 CH═CH.sub.25            4-Cl, 6-F                 CH.sub.3  NH.sub.26            4-Cl, 6-F                 CH.sub.3  CH.sub.2 C.tbd.CH7            4-Cl, 6-F                 CH.sub.3  C.sub.3 H.sub.78            4-Cl, 6-F                 CH.sub.3  CH.sub.2 OCH.sub.39            4-Cl, 6-F                 CH.sub.3  CH.sub.2 CO.sub.2 C.sub.2 H.sub.5______________________________________ 
    
     
                                           TABLE 2__________________________________________________________________________ ##STR17## ##STR18## ##STR19## ##STR20## ##STR21##               Double               BondNo.   A        B       Posit&#39;n                   X     R            J__________________________________________________________________________ 10   N        O       1-2 4-Cl  CH.sub.3     J1 11   N        O       1-2 4-Cl  C.sub.2 H.sub.5                                      J1 12   N        O       1-2 4-Cl  CH(CH.sub.3).sub.2                                      J1 13   N        O       1-2 4,6-Cl.sub.2                         CH.sub.3     J1 14   N        O       1-2 4,6-Cl.sub.2                         C.sub.2 H.sub.5                                      J1 15   N        O       1-2 4,6-Cl.sub.2                         C.sub.2 H.sub.5                                      J1 16   N        O       1-2 4-Br, 6-F                         CH.sub.3     J1 17   N        O       1-2 4-CF.sub.3, 6-F                         CH.sub.3     J1 18   N        O       1-2 4,6-F.sub.2                         CH.sub.3     J1 19   N        O       1-2 4-CN, 6-F                         CH.sub.3     J1 20   N        O       1-2 4-OCF.sub.3, 6-F                         CH.sub.3     J1 21   N        O       1-2 4-Br, 6-F                         C.sub.2 H.sub.5                                      J1 22   N        O       1-2 4-CN, 6-F                         C.sub.2 H.sub.5                                      J1 23   N        O       1-2 4-CN, 6-F                         CH(CH.sub.3).sub.2                                      J1 24   N        O       1-2 4-CH.sub.3, 6-F                         CH.sub.3     J1 25   N        O       1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1 26   N        O       1-2 4-Cl, 6-F                         C.sub.3 H.sub.7                                      J1 27   N        O       1-2 4-Cl, 6-F                         C.sub.4 H.sub.9                                      J1 28   N        O       1-2 4-Cl, 6-F                         CH(CH.sub.3).sub.2                                      J1 29   N        O       1-2 4-Cl, 6-F                         CH.sub.2 CH(CH.sub.3).sub.2                                      J1 30   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.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.sub.3     J1 34   N        O       1-2 4-Cl, 6-F                         CCl.sub.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.sub.2     J1 39   N        O       1-2 4-Cl, 6-F                         NHCH.sub.3   J1 40   N        O       1-2 4-Cl, 6-F                         N(CH.sub.3).sub.2                                      J1 41   N        O       1-2 4-Cl, 6-F                         NHCH.sub.2 CO.sub.2 CH.sub.3                                      J1 42   N        O       1-2 4-Cl, 6-F                         NHSO.sub.2 CH.sub.3                                      J1 43   N        O       1-2 4-Br, 6-F                         NHCOCH.sub.3 J1 44   N        O       1-2 4-Cl, 6-F                         morpholino   J1 45   N        O       1-2 4-Cl, 6-F                         NHSO.sub.2 C.sub.6 H.sub.5                                      J1 46   N        O       1-2 4-Cl, 6-F                         NHSO.sub.2 CH.sub.2 C.sub.6 H.sub.5                                      J1 47   N        O       1-2 4-Cl, 6-F                         N(CH.sub.3)SO.sub.2 CH.sub.3                                      J1 48   N        O       1-2 4-Cl, 6-F                         NHPO(OCH.sub.3).sub.2                                      J1 49   N        O       1-2 4-Br, 6-F                         CH.sub.2 CO.sub.2 CH.sub.3                                      J1 50   N        O       1-2 4-Cl, 6-F                         C.sub.2 H.sub.4 CO.sub.2 CH.sub.3                                      J1 51   N        O       1-2 4-Cl, 6-F                         CH═CHCO.sub.2 CH.sub.3                                      J1 52   N        O       1-2 4-Cl, 6-F                         CH═C(Cl)CO.sub.2 CH.sub.3                                      J1 53   N        O       1-2 4-Cl, 6-F                         CH.sub.2 CH(Cl)CO.sub.2 CH.sub.3                                      J1 54   N        O       1-2 4-Cl, 6-F                         OCH.sub.3    J1 55   N        O       1-2 4-Cl, 6-F                         OC.sub.2 H.sub.5                                      J1 56   N        O       1-2 4-Cl, 6-F                         OCH(CH.sub.3).sub.2                                      J1 57   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 CH═CH.sub.2                                      J1 58   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 C(CH.sub.3)═CH.sub.2                                      J1 59   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 CCH                                      J1 60   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                                      J1 61   N        O       1-2 4-Cl, 6-F                         OCH(CH.sub.3)CO.sub.2 CH.sub.3                                      J1 62   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 CN J1 63   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 CONH.sub.2                                      J1 64   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 CONHCH.sub.3                                      J1 65   N        O       1-2 4-Cl, 6-F                         OCH(CH.sub.3)CONH.sub.2                                      J1 66   N        O       1-2 4-Cl, 6-F                         OCH(CH.sub.3)CONHCH.sub.3                                      J1 67   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 CO.sub.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.sub.6 H.sub.4 OCH(CH.sub.3)CO.sub.2                         CH.sub.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.sub.2 CH.sub.3                                      J1 74   N        O       1-2 4-Cl, 6-F                         CO.sub.2 H   J1 75   N        O       1-2 4-Cl, 6-F                         CO.sub.2 Na  J1 76   N        O       1-2 4-Cl, 6-F                         CONH.sub.2   J1 77   N        O       1-2 4-Cl, 6-F                         CONHCH.sub.3 J1 78   N        O       1-2 4-Cl, 6-F                         CON(CH.sub.3).sub.2                                      J1 79   N        O       1-2 4-Cl, 6-F                         CONHSO.sub.2 CH.sub.3                                      J1 80   N        O       1-2 4-Cl, 6-F                         CO.sub.2 NHOCH.sub.3                                      J1 81   N        O       1-2 4-Cl, 6-F                         SCH.sub.3    J1 82   N        O       1-2 4-Cl, 6-F                         SCH.sub.2 CO.sub.2 CH.sub.3                                      J1 83   N        O       1-2 4-Cl, 6-F                         SCH.sub.2 CONH.sub.2                                      J1 84   N        O       1-2 4-Cl, 6-F                         SO.sub.2 CH.sub.3                                      J1 85   N        O       1-2 4-Cl, 6-F                         SH           J1 86   N        O       1-2 4-Cl, 6-F                         CH.sub.2 OH  J1 87   N        O       1-2 4-Cl, 6-F                         CH(CH.sub.3)OH                                      J1 88   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 OH                                      J1 89   N        O       1-2 4-Cl, 6-F                         C.sub.2 H.sub.4 OH                                      J1 90   N        O       1-2 4-Cl, 6-F                         CH.sub.2 CH(CH.sub.3)OH                                      J1 91   N        O       1-2 4-Cl, 6-F                         CH.sub.2 C(CH.sub.3).sub.2 OH                                      J1 92   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 OCOCH.sub.3                                      J1 93   N        O       1-2 4-Cl, 6-F                         CH(CH.sub.3).sub.2 OCOCH.sub.3                                      J1 94   N        O       1-2 4-Cl, 6-F                         CH(CH.sub.3)OCOCH.sub.3                                      J1 95   N        O       1-2 4-Cl, 6-F                         CHBr.sub.2   J1 96   N        O       1-2 4-Br, 6-F                         CH.sub.2 OCH.sub.3                                      J1 97   N        O       1-2 4-Cl, 6-F                         CH.sub.2 OCH.sub.2 CCH                                      J1 98   N        O       1-2 4-Br, 6-F                         NH.sub.2     J1 99   N        O       1-2 4-Br, 6-F                         phenoxymethyl                                      J1100   N        O       1-2 4-Br, 6-F                         N(COCH.sub.3).sub.2                                      J1101   N        O       1-2 4-Br, 6-F                         CH.sub.2 OCOCH.sub.3                                      J1102   N        O       1-2 4-Br, 6-F                         4-chlorophenoxymethyl                                      J1103   N        O       1-2 4-Br, 6-F                         CH(Ph)OCOCH.sub.3                                      J1104   N        O       1-2 4-Br, 6-F                         C(CH.sub.3).sub.2 OCOCH.sub.3                                      J1105   N        O       1-2 4-Br, 6-F                         CO.sub.2 H   J1106   N        O       1-2 4-Br, 6-F                         OCH.sub.2 CCH                                      J1107   N        O       1-2 4-Br, 6-F                         OCH(CH.sub.3).sub.2                                      J1108   N        O       1-2 4-Br, 6-F                         NHSO.sub.2 CH.sub.3                                      J1109   N        O       1-2 4-Br, 6-F                         OCH.sub.3    J1110   N        O       1-2 4-Br, 6-F                         OCH.sub.2 CH═CH.sub.2                                      J1111   N        O       1-2 4-Cl, 6-F                         (CH.sub.3)(CN)OH                                      J1112   N        O       1-2 4-Cl, 6-F                         CH.sub.3     J2113   N        O       1-2 4-Cl, 6-F                         n-C.sub.3 H.sub.7                                      J2114   N        O       1-2 4-Cl, 6-F                         i-C.sub.3 H.sub.7                                      J2115   N        O       1-2 4-Cl, 6-F                         t-C.sub.4 H.sub.9                                      J2116   N        O       1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J2117   N        O       1-2 4-Cl, 6-F                         CH.sub.2 CO.sub.2 CH.sub.3                                      J2118   N        O       1-2 4-Cl, 6-F                         phenoxymethyl                                      J2119   N        O       1-2 4-Cl, 6-F                         CONHCH.sub.3 J2120   N        O       1-2 4-Cl, 6-F                         CON(CH.sub.3).sub.2                                      J2121   N        O       1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J2122   N        O       1-2 4-Cl, 6-F                         Phenyl       J2123   N        O       1-2 4-Cl, 6-F                         SCH.sub.3    J2124   N        O       1-2 4-Cl, 6-F                         CH.sub.2 OCH.sub.3                                      J2125   N        O       1-2 4-Cl, 6-F                         Benzyl       J2126   N        O       1-2 4-Cl, 6-F                         4-chlorophenylmethyl                                      J2127   N        O       1-2 4-Cl, 6-F                         SO.sub.2 CH.sub.3                                      J2128   N        O       1-2 4-Cl, 6-F                         CF.sub.3     J2129   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 OCO.sub.2 CH.sub.3                                      J2130   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 CH.sub.2 OH                                      J2131   N        O       1-2 4-Cl, 6-F                         CH.sub.3     J3132   N        O       1-2 4-Cl, 6-F                         n-C.sub.3 H.sub.7                                      J3133   N        O       1-2 4-Cl, 6-F                         i-C.sub.3 H.sub.7                                      J3134   N        O       1-2 4-Cl, 6-F                         t-C.sub.4 H.sub.9                                      J3135   N        O       1-2 4-Cl, 6-F                         CH.sub.2 OH  J3136   N        O       1-2 4-Cl, 6-F                         CH.sub.2 CH.sub.2 OH                                      J3137   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 OH                                      J3138   N        O       1-2 4-Cl, 6-F                         CONHCH.sub.3 J3139   N        O       1-2 4-Cl, 6-F                         CON(CH.sub.3).sub.2                                      J3140   N        O       1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J3141   N        O       1-2 4-Cl, 6-F                         Phenyl       J3142   N        O       1-2 4-Cl, 6-F                         SCH.sub.3    J3143   N        O       1-2 4-Cl, 6-F                         CH.sub.2 OCH.sub.3                                      J3144   N        O       1-2 4-Cl, 6-F                         Benzyl       J3145   N        O       1-2 4-Cl, 6-F                         4-chlorophenylmethyl                                      J3146   N        O       1-2 4-Cl, 6-F                         SO.sub.2 CH.sub.3                                      J3147   N        O       1-2 4-Cl, 6-F                         CF.sub.3     J3148   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 OCO.sub.2 CH.sub.3                                      J3149   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 CH.sub.2 OH                                      J3150   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3                                      J3151   N        O       1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J3152   N        O       1-2 4-Cl, 6-F                         CO.sub.2 Na  J3153   N        O       1-2 4-Cl, 6-F                         CONHSO.sub.2 CH.sub.3                                      J3154   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 CO.sub.2 CH.sub.3                                      J3155   N        O       1-2 4-Cl, 6-F                         OCH(CH.sub.3)CO.sub.2 CH.sub.3                                      J3156   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 CH═CH.sub.2                                      J3157   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 CCH                                      J3158   N        O       1-2 4-Cl, 6-F                         OH           J3159   N        O       1-2 4-Cl, 6-F                         OCH.sub.3    J3160   N        O       1-2 4-Cl, 6-F                         OCH(CH.sub.3).sub.2                                      J3161   N        O       1-2 4-Cl, 6-F                         CH.sub.3     J4162   N        O       1-2 4-Cl, 6-F                         n-C.sub.3 H.sub.7                                      J4163   N        O       1-2 4-Cl, 6-F                         i-C.sub.3 H.sub.7                                      J4164   N        O       1-2 4-Cl, 6-F                         t-C.sub.4 H.sub.9                                      J4165   N        O       1-2 4-Cl, 6-F                         CH.sub.2 OH  J4166   N        O       1-2 4-Cl, 6-F                         CH.sub.2 CH.sub.2 OH                                      J4167   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 OH                                      J4168   N        O       1-2 4-Cl, 6-F                         CONHCH.sub.3 J4169   N        O       1-2 4-Cl, 6-F                         CON(CH.sub.3).sub.2                                      J4170   N        O       1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J4171   N        O       1-2 4-Cl, 6-F                         Phenyl       J4172   N        O       1-2 4-Cl, 6-F                         SCH.sub.3    J4173   N        O       1-2 4-Cl, 6-F                         CH.sub.2 OCH.sub.3                                      J4174   N        O       1-2 4-Cl, 6-F                         Benzyl       J4175   N        O       1-2 4-Cl, 6-F                         4-chlorophenylmethyl                                      J4176   N        O       1-2 4-Cl, 6-F                         SO.sub.2 CH.sub.3                                      J4177   N        O       1-2 4-Cl, 6-F                         CF.sub.3     J4178   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 OCO.sub.2 CH.sub.3                                      J4179   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 CH.sub.2 OH                                      J4180   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3                                      J4181   N        O       1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J4182   N        O       1-2 4-Cl, 6-F                         CO.sub.2 Na  J4183   N        O       1-2 4-Cl, 6-F                         CONHSO.sub.2 CH.sub.3                                      J4184   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 CO.sub.2 CH.sub.3                                      J4185   N        O       1-2 4-Cl, 6-F                         OCH(CH.sub.3)CO.sub.2 CH.sub.3                                      J4186   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 CH═CH.sub.2                                      J4187   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 C.tbd.CH                                      J4188   N        O       1-2 4-Cl, 6-F                         OH           J4189   N        O       1-2 4-Cl, 6-F                         OCH.sub.3    J4190   N        O       1-2 4-Cl, 6-F                         OCH(CH.sub.3).sub.2                                      J4191   N        O       1-2 4-Cl, 6-F                         CH.sub.3     J5192   N        O       1-2 4-Cl, 6-F                         n-C.sub.3 H.sub.7                                      J5193   N        O       1-2 4-Cl, 6-F                         i-C.sub.3 H.sub.7                                      J5194   N        O       1-2 4-Cl, 6-F                         t-C.sub.4 H.sub.9                                      J5195   N        O       1-2 4-Cl, 6-F                         CH.sub.2 OH  J5196   N        O       1-2 4-Cl, 6-F                         CH.sub.2 CH.sub.2 OH                                      J5197   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 OH                                      J5198   N        O       1-2 4-Cl, 6-F                         CONHCH.sub.3 J5199   N        O       1-2 4-Cl, 6-F                         CON(CH.sub.3).sub.2                                      J5200   N        O       1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J5201   N        O       1-2 4-Cl, 6-F                         Phenyl       J5202   N        O       1-2 4-Cl, 6-F                         SCH.sub.3    J5203   N        O       1-2 4-Cl, 6-F                         CH.sub.2 OCH.sub.3                                      J5204   N        O       1-2 4-Cl, 6-F                         Benzyl       J5205   N        O       1-2 4-Cl, 6-F                         4-chlorophenylmethyl                                      J5206   N        O       1-2 4-Cl, 6-F                         SO.sub.2 CH.sub.3                                      J5207   N        O       1-2 4-Cl, 6-F                         CF.sub.3     J5208   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 OCO.sub.2 CH.sub.3                                      J5209   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 CH.sub.2 OH                                      J5210   N        O       1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3                                      J5211   N        O       1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J5212   N        O       1-2 4-Cl, 6-F                         CO.sub.2 Na  J5213   N        O       1-2 4-Cl, 6-F                         CONHSO.sub.2 CH.sub.3                                      J5214   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 CO.sub.2 CH.sub.3                                      J5215   N        O       1-2 4-Cl, 6-F                         OCH(CH.sub.3)CO.sub.2 CH.sub.3                                      J5216   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 CH═CH.sub.2                                      J5217   N        O       1-2 4-Cl, 6-F                         OCH.sub.2 CCH                                      J5218   N        O       1-2 4-Cl, 6-F                         OH           J5219   N        O       1-2 4-Cl, 6-F                         OCH.sub.3    J5220   N        O       1-2 4-Cl, 6-F                         OCH(CH.sub.3).sub.2                                      J5221   O        CH      2-3 4-Cl  CH.sub.3     J1222   O        CH      2-3 4-Cl, 6-F                         CH.sub.3     J1223   O        CH      2-3 4-Cl, 6-F                         n-propyl     J1224   O        CH      2-3 4-Cl, 6-F                         isopropyl    J1225   O        CH      2-3 4-Cl  n-butyl      J1226   O        CH      2-3 4-Cl  t-butyl      J1227   O        CH      2-3 4-Cl, 6-F                         t-butyl      J1228   O        CH      2-3 4,6-F.sub.2                         t-butyl      J1229   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)C.sub.3 H.sub.7                                      J1230   O        CH      2-3 4-Cl, 6-F                         CH═CH.sub.2                                      J1231   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3)═CH.sub.2                                      J1232   O        CH      2-3 4-Cl  CH.sub.2 Br  J1233   O        CH      2-3 4-Cl  CHBr.sub.2   J1234   O        CH      2-3 4-Cl, 6-F                         CH(Cl)CH.sub.3                                      J1235   O        CH      2-3 4-Cl, 6-F                         CH(F)CH.sub.3                                      J1236   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 Cl                                      J1237   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 F                                      J1238   O        CH      2-3 4-Cl  CH.sub.2 OH  J1239   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 OH                                      J1240   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OH                                      J1241   O        CH      2-3 4-Cl  C(CH.sub.3).sub.2 OH                                      J1242   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 OH                                      J1243   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH(CH.sub.3)OH                                      J1244   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OC(CH.sub.3).sub.3                                      J1245   O        CH      2-3 4-Cl, 6-F                         CH(OC.sub.2 H.sub.5).sub.2                                      J1246   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OCOCH.sub.3                                      J1247   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OCOCH(CH.sub.3).sub.2                                      J1248   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OCOPh                                      J1249   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OCONHCH.sub.3                                      J1250   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OCONHCH.sub.2 Ph                                      J1251   O        CH      2-3 4-Cl  C(CH.sub.3).sub.2 OCH.sub.3                                      J1252   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 OCH.sub.2 OCH.sub.3                                      J1253   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 OCOCH.sub.3                                      J1254   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 NH.sub.2                                      J1255   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 NHSO.sub.2 CH.sub.3                                      J1256   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 CH.sub.2 CN                                      J1257   O        CH      2-3 4-Cl  CH.sub.2 N(C.sub.2 H.sub.5).sub.2                                      J1258   O        CH      2-3 4-Cl  CH═NOH   J1259   O        CH      2-3 4-Cl  CH═NOCH.sub.3                                      J1260   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 OCOCH.sub.3                                      J1261   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 OCONHCH.sub.3                                      J1262   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 CO.sub.2 H                                      J1263   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                                      J1264   O        CH      2-3 4-Cl  Phenyl       J1265   O        CH      2-3 4-Cl  CHO          J1266   O        CH      2-3 4-Cl  CO.sub.2 H   J1267   O        CH      2-3 H     CO.sub.2 C.sub.2 H.sub.5                                      J1268   O        CH      2-3 4-Cl  CO.sub.2 C.sub.2 H.sub.5                                      J1269   O        CH      2-3 4-Cl  CONH.sub.2   J1270   O        CH      2-3 4-Cl  CONHCH.sub.3 J1271   O        CH      2-3 4-Cl  CON(CH.sub.3).sub.2                                      J1272   O        CH      2-3 4-Cl  NHCO.sub.2 C(CH.sub.3).sub.3                                      J1273   O        CH      2-3 4-Cl, 6-F                         CONH.sub.2   J1274   O        CH      2-3 4-Cl, 6-F                         CONH(CH.sub.3)                                      J1275   O        CH      2-3 4-Cl, 6-F                         CON(CH.sub.3).sub.2                                      J1276   O        CH      2-3 4-Cl, 6-F                         CO.sub.2 H   J1277   O        CH      2-3 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J1278   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 OH  J1279   O        CH      2-3 4-Cl, 6-F                         3,4-dimethoxyphenyl                                      J1280   O        CH      2-3 4-Cl, 6-F                         Phenyl       J1281   O        CH      2-3 4-Cl, 6-F                         CH.sub.3     J2282   O        CH      2-3 4-Cl, 6-F                         n-propyl     J2283   O        CH      2-3 4-Cl, 6-F                         isopropyl    J2284   O        CH      2-3 4-Cl, 6-F                         t-butyl      J2285   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)C.sub.3 H.sub.7                                      J2286   O        CH      2-3 4-Cl, 6-F                         CH═CH.sub.2                                      J2287   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3)═CH.sub.2                                      J2288   O        CH      2-3 4-Cl, 6-F                         CH(Cl)CH.sub.3                                      J2289   O        CH      2-3 4-Cl, 6-F                         CH(F)CH.sub.3                                      J2290   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 Cl                                      J2291   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 F                                      J2292   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 OH                                      J2293   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OH                                      J2294   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 OH                                      J2295   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH(CH.sub.3)OH                                      J2296   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OC(CH.sub.3).sub.3                                      J2297   O        CH      2-3 4-Cl, 6-F                         CH(OC.sub.2 H.sub.5).sub.2                                      J2298   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OCOCH.sub.3                                      J2299   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OCOCH(CH.sub.3).sub.2                                      J2300   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OCOPh                                      J2301   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OCONHCH.sub.3                                      J2302   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OCONHCH.sub.2 Ph                                      J2303   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 OCH.sub.2 OCH.sub.3                                      J2304   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 OCOCH.sub.3                                      J2305   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 NH.sub.2                                      J2306   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 NHSO.sub.2 CH.sub.3                                      J2307   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 CH.sub.2 CN                                      J2308   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 OCOCH.sub.3                                      J2309   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 OCONHCH.sub.3                                      J2310   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 CO.sub.2 H                                      J2311   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                                      J2312   O        CH      2-3 4-Cl, 6-F                         CONH.sub.2   J2313   O        CH      2-3 4-Cl, 6-F                         CONH(CH.sub.3)                                      J2314   O        CH      2-3 4-Cl, 6-F                         CON(CH.sub.3).sub.2                                      J2315   O        CH      2-3 4-Cl, 6-F                         CO.sub.2 H   J2316   O        CH      2-3 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J2317   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 OH  J2318   O        CH      2-3 4-Cl, 6-F                         3,4-dimethoxyphenyl                                      J2319   O        CH      2-3 4-Cl, 6-F                         Phenyl       J2320   O        CH      2-3 4-Cl, 6-F                         CH.sub.3     J3321   O        CH      2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J3322   O        CH      2-3 4-Cl, 6-F                         CH(Cl)CH.sub.3                                      J3323   O        CH      2-3 4-Cl, 6-F                         CH(F)CH.sub.3                                      J3324   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 Cl                                      J3325   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 F                                      J3326   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 OH                                      J3327   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OH                                      J3328   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 OH                                      J3329   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 OCH.sub.2 OCH.sub.3                                      J3330   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 NHSO.sub.2 CH.sub.3                                      J3331   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 CH.sub.2 CN                                      J3332   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                                      J3333   O        CH      2-3 4-Cl, 6-F                         CON(CH.sub.3).sub.2                                      J3334   O        CH      2-3 4-Cl, 6-F                         CH.sub.3     J4335   O        CH      2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J4336   O        CH      2-3 4-Cl, 6-F                         CH(Cl)CH.sub.3                                      J4337   O        CH      2-3 4-Cl, 6-F                         CH(F)CH.sub.3                                      J4338   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 Cl                                      J4339   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 F                                      J4340   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 OH                                      J4341   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OH                                      J4342   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 OH                                      J4343   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 OCH.sub.2 OCH.sub.3                                      J4344   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 NHSO.sub.2 CH.sub.3                                      J4345   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 CH.sub.2 CN                                      J4346   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                                      J4347   O        CH      2-3 4-Cl, 6-F                         CON(CH.sub.3).sub.2                                      J4348   O        CH      2-3 4-Cl, 6-F                         CH.sub.3     J5349   O        CH      2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J5350   O        CH      2-3 4-Cl, 6-F                         CH(Cl)CH.sub.3                                      J5351   O        CH      2-3 4-Cl, 6-F                         CH(F)CH.sub.3                                      J5352   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 Cl                                      J5353   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 F                                      J5354   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 OH                                      J5355   O        CH      2-3 4-Cl, 6-F                         CH(CH.sub.3)OH                                      J5356   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 OH                                      J5357   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 OCH.sub.2 OCH.sub.3                                      J5358   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 NHSO.sub.2 CH.sub.3                                      J5359   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 CH.sub.2 CN                                      J5360   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                                      J5361   O        CH      2-3 4-Cl, 6-F                         CON(CH.sub.3).sub.2                                      J5362   NH       N       2-3 4-Cl, 6-F                         H            J1363   NH       N       2-3 4-Cl, 6-F                         CH.sub.3     J1364   NH       N       2-3 4-Cl, 6-F                         CHF.sub.2    J1365   NH       N       2-3 4-Cl, 6-F                         CF.sub.3     J1366   NH       N       2-3 4-Cl, 6-F                         CClF.sub.2   J1367   NH       N       2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1368   NH       N       2-3 4-Cl, 6-F                         i-C.sub.3 H.sub.7                                      J1369   NH       N       2-3 4-Cl, 6-F                         t-C.sub.4 H.sub.9                                      J1370   NH       N       2-3 4-Cl, 6-F                         CH.sub.2 OCH.sub.3                                      J1371   NH       N       2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 OC(O)CH.sub.3                                      J1372   NH       N       2-3 4-Cl, 6-F                         C.sub.2 H.sub.4 CO.sub.2 C.sub.2 H.sub.5                                      J1373   NH       N       2-3 4-Cl, 6-F                         Cyclohexyl   J1374   NH       N       2-3 4-Cl, 6-F                         Adamantyl    J1375   NH       N       2-3 4-Cl, 6-F                         Phenyl       J1376   NH       N       2-3 4-Cl, 6-F                         Benzyl       J1377   NH       N       2-3 4-Cl, 6-F                         CH(CH.sub.3)C.sub.6 H.sub.5                                      J1378   NH       N       2-3 4-Cl, 6-F                         CH.sub.2 OC.sub.6 H.sub.5                                      J1379   NH       N       2-3 4-Cl, 6-F                         C.sub.2 H.sub.4 C.sub.8 H.sub.5                                      J1380   NH       N       2-3 4-Cl, 6-F                         C.sub.3 H.sub.6 C.sub.6 H.sub.5                                      J1381   NH       N       2-3 4-Cl, 6-F                         2-chlorophenylmethyl                                      J1382   NH       N       2-3 4-Cl, 6-F                         3-chlorophenylmethyl                                      J1383   NH       N       2-3 4-Cl, 6-F                         4-chlorophenylmethyl                                      J1384   NH       N       2-3 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J1385   NH       N       2-3 4-Cl, 6-F                         Furan-2-yl   J1386   NH       N       2-3 4-Cl, 6-F                         CH.sub.2 Cl  J1387   NH       N       2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 CH.sub.2 Cl                                      J1388   NH       N       2-3 4-Cl, 6-F                         OC.sub.2 H.sub.5                                      J1389   N        NH      1-2 4-Cl, 6-F                         CH.sub.3     J1390   N        NH      1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1391   N        NH      1-2 4-Cl, 6-F                         isopropyl    J1392   N        NH      1-2 4-Cl, 6-F                         t-butyl      J1393   N        NH      1-2 4-Cl, 6-F                         CF.sub.3     J1394   N        NH      1-2 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J1395   N        NCH.sub.3               1-2 4-Cl, 6-F                         CH.sub.3     J1396   N        NCH.sub.3               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1397   N        NCH.sub.3               1-2 4-Cl, 6-F                         isopropyl    J1398   N        NCH.sub.3               1-2 4-Cl, 6-F                         t-butyl      J1399   N        NCH.sub.3               1-2 4-Cl, 6-F                         CF.sub.3     J1400   N        NCH.sub.3               1-2 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J1401   N        NCH.sub.3               1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.2 CH.sub.3                                      J1402   N        NC.sub.2 H.sub.5               1-2 4-Cl, 6-F                         CH.sub.3     J1403   N        NC.sub.2 H.sub.5               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1404   NH       NH      --  4-NO.sub.2, 6-F                         CF.sub.3     J1405   N.sup.- H.sub.3 N.sup.+ CH(CH.sub.3).sub.2       N       2-3 4-Cl, 6-F                         CH.sub.3     J1406   NCH.sub.3       N       2-3 4-Cl, 6-F                         CF.sub.3     J1407   NCH.sub.3       NC.sub.2 H.sub.5               1-2 4-Cl, 6-F                         isopropyl    J1408   N        NC.sub.2 H.sub.5               1-2 4-Cl, 6-F                         t-butyl      J1409   N        NC.sub.2 H.sub.5               1-2 4-Cl, 6-F                         CF.sub.3     J1410   N        NC.sub.2 H.sub.5               1-2 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J1411   N        NC.sub.4 H.sub.9               1-2 4-Cl, 6-F                         CH.sub.3     J1412   N        NC.sub.4 H.sub.9               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1413   N        NC.sub.4 H.sub.9               1-2 4-Cl, 6-F                         isopropyl    J1414   N        NC.sub.4 H.sub.9               1-2 4-Cl, 6-F                         t-butyl      J1415   N        NC.sub.4 H.sub.9               1-2 4-Cl, 6-F                         CF.sub.3     J1416   N        NC.sub.4 H.sub.9               1-2 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J1417   N        NCH.sub.2 OCH.sub.3               1-2 4-Cl, 6-F                         CH.sub.3     J1418   N        NCH.sub.2 OCH.sub.3               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1419   N        NCH.sub.2 OCH.sub.3               1-2 4-Cl, 6-F                         isopropyl    J1420   N        NCH.sub.2 OCH.sub.3               1-2 4-Cl, 6-F                         t-butyl      J1421   N        NCH.sub.2 OCH.sub.3               1-2 4-Cl, 6-F                         CF.sub.3     J1422   N        NCH.sub.2 OCH.sub.3               1-2 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J1423   N        NCO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         CH.sub.3     J1424   N        NCO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1425   N        NCO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         isopropyl    J1426   N        NCO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         t-butyl      J1427   N        NCO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         CF.sub.3     J1428   N        NCO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J1429   N        NSO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         CH.sub.3     J1430   N        NSO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1431   N        NSO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         isopropyl    J1432   N        NSO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         t-butyl      J1433   N        NSO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         CF.sub.3     J1434   N        NSO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J1435   N        NCH.sub.2 CHCH.sub.2               1-2 4-Cl, 6-F                         CH.sub.3     J1436   N        NCH.sub.2 CHCH.sub.2               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1437   N        NCH.sub.2 CHCH.sub.2               1-2 4-Cl, 6-F                         isopropyl    J1438   N        NCH.sub.2 CHCH.sub.2               1-2 4-Cl, 6-F                         t-butyl      J1439   N        NCH.sub.2 CHCH.sub.2               1-2 4-Cl, 6-F                         CF.sub.3     J1440   N        NCH.sub.2 CHCH.sub.2               1-2 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J1441   N        NCH.sub.2 CCH               1-2 4-Cl, 6-F                         CH.sub.3     J1442   N        NCH.sub.2 CCH               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1443   N        NCH.sub.2 CCH               1-2 4-Cl, 6-F                         isopropyl    J1444   N        NCH.sub.2 CCH               1-2 4-Cl, 6-F                         t-butyl      J1445   N        NCH.sub.2 CCH               1-2 4-Cl, 6-F                         CF.sub.3     J1446   N        NCH.sub.2 CCH               1-2 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J1447   N        NCH.sub.2 CO.sub.2 Me               1-2 4-Cl, 6-F                         CH.sub.3     J1448   N        NCH.sub.2 CO.sub.2 Me               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1449   N        NCH.sub.2 CO.sub.2 Me               1-2 4-Cl, 6-F                         isopropyl    J1450   N        NCH.sub.2 CO.sub.2 Me               1-2 4-Cl, 6-F                         t-butyl      J1451   N        NCH.sub.2 CO.sub.2 Me               1-2 4-Cl, 6-F                         CF.sub.3     J1452   N        NCH.sub.2 CO.sub.2 Me               1-2 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J1453   N        NCF.sub.3               1-2 4-Cl, 6-F                         CH.sub.3     J1454   N        NCF.sub.3               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1455   N        NCH.sub.2 CO.sub.2 Me               1-2 4-Cl, 6-F                         isopropyl    J1456   N        NCH.sub.2 CO.sub.2 Me               1-2 4-Cl, 6-F                         t-butyl      J1457   N        NCH.sub.2 CO.sub.2 Me               1-2 4-Cl, 6-F                         CF.sub.3     J1458   N        NCF.sub.3               1-2 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J1459   NH       N       2-3 4-Cl, 6-F                         CH.sub.3     J2460   NH       N       2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J2461   NH       N       2-3 4-Cl, 6-F                         isopropyl    J2462   NH       N       2-3 4-Cl, 6-F                         t-butyl      J2463   NH       N       2-3 4-Cl, 6-F                         CF.sub.3     J2464   NH       N       2-3 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J2465   NH       N       2-3 4-Cl, 6-F                         CH.sub.3     J3466   NH       N       2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J3467   NH       N       2-3 4-Cl, 6-F                         isopropyl    J3468   NH       N       2-3 4-Cl, 6-F                         t-butyl      J3469   NH       N       2-3 4-Cl, 6-F                         CF.sub.3     J3470   NH       N       2-3 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J3471   NH       N       2-3 4-Cl, 6-F                         CH.sub.3     J4472   NH       N       2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J4473   NH       N       2-3 4-Cl, 6-F                         isopropyl    J4474   NH       N       2-3 4-Cl, 6-F                         t-butyl      J4475   NH       N       2-3 4-Cl, 6-F                         CF.sub.3     J4476   NH       N       2-3 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J4477   NH       N       2-3 4-Cl, 6-F                         CH.sub.3     J5478   NH       N       2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J5479   NH       N       2-3 4-Cl, 6-F                         isopropyl    J5480   NH       N       2-3 4-Cl, 6-F                         t-butyl      J5481   NH       N       2-3 4-Cl, 6-F                         CF.sub.3     J5482   NH       N       2-3 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J5483   NH       NH      1-2 4-Cl, 6-F                         CH.sub.3     J1484   CH       NH      1-2 4-Cl, 6-F                         n-C.sub.3 H.sub.7                                      J1485   CH       NH      1-2 4-Cl, 6-F                         i-C.sub.3 H.sub.7                                      J1486   CH       NH      1-2 4-Cl, 6-F                         t-C.sub.4 H.sub.9                                      J1487   CH       NH      1-2 4-Cl, 6-F                         CH.sub.2 OH  J1488   CH       NH      1-2 4-Cl, 6-F                         CH.sub.2 CH.sub.2 OH                                      J1489   CH       NH      1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 OH                                      J1490   CH       NH      1-2 4-Cl, 6-F                         CONHCH.sub.3 J1491   CH       NH      1-2 4-Cl, 6-F                         CON(CH.sub.3).sub.2                                      J1492   CH       NH      1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J1493   CH       NH      1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.2 CH.sub.3                                      J1494   CH       NH      1-2 4-Cl, 6-F                         Phenyl       J1495   CH       NH      1-2 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J1496   CH       NH      1-2 4-Cl, 6-F                         CH.sub.2 OCH.sub.3                                      J1497   CH       NH      1-2 4-Cl, 6-F                         Benzyl       J1498   CH       NH      1-2 4-Cl, 6-F                         4-chlorophenylmethyl                                      J1499   CH       NH      1-2 4-Cl, 6-F                         SO.sub.2 CH.sub.3                                      J1500   CH       NH      1-2 4-Cl, 6-F                         CF.sub.3     J1501   CH       NH      1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 OCOCH.sub.3                                      J1502   CH       NH      1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 CH.sub.2 OH                                      J1503   CH       NH      1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3                                      J1504   CH       NH      1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1505   CH       NH      1-2 4-Cl, 6-F                         CO.sub.2 Na  J1506   CH       NH      1-2 4-Cl, 6-F                         CONHSO.sub.2 CH.sub.3                                      J1507   CH       NH      1-2 4-Cl, 6-F                         CHFCH.sub.3  J1508   CH       NH      1-2 4-Cl, 6-F                         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                      J1509   CH       NCH.sub.3               1-2 4-Cl, 6-F                         CH.sub.3     J1510   CH       NCH.sub.3               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1511   CH       NCH.sub.3               1-2 4-Cl, 6-F                         isopropyl    J1512   CH       NCH.sub.3               1-2 4-Cl, 6-F                         t-butyl      J1513   CH       NCH.sub.3               1-2 4-Cl, 6-F                         CF.sub.3     J1514   CH       NCH.sub.3               1-2 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J1515   CH       NCH.sub.3               1-2 4-Cl, 6-F                         CHFCH.sub.3  J1516   CH       NCH.sub.3               1-2 4-Cl, 6-F                         CON(CH.sub.3).sub.2                                      J1517   CH       NCH.sub.3               1-2 4-Cl, 6-F                         CH.sub.2 CO.sub.2 C.sub.2 H.sub.5                                      J1518   CH       NCH.sub.3               1-2 4-Cl, 6-F                         CH.sub.2 CH.sub.2 CN                                      J1519   CH       NCH.sub.3               1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 OH                                      J1520   CH       NCH.sub.3               1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 OCOCH.sub.3                                      J1521   CH       NCH.sub.3               1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 NHSO.sub.2 CH.sub.3                                      J1522   CH       NCH.sub.3               1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.2 CH.sub.3                                      J1523   CH       NC.sub.2 H.sub.5               1-2 4-Cl, 6-F                         CH.sub.3     J1524   CH       NC.sub.2 H.sub.5               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1525   CH       NC.sub.2 H.sub.5               1-2 4-Cl, 6-F                         isopropyl    J1526   CH       NC.sub.2 H.sub.5               1-2 4-Cl, 6-F                         t-butyl      J1527   CH       NC.sub.2 H.sub.5               1-2 4-Cl, 6-F                         CF.sub.3     J1528   CH       NC.sub.2 H.sub.5               1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J1529   CH       NC.sub.4 H.sub.9               1-2 4-Cl, 6-F                         CH.sub.3     J1530   CH       NC.sub.4 H.sub.9               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1531   CH       NC.sub.4 H.sub.9               1-2 4-Cl, 6-F                         isopropyl    J1532   CH       NC.sub.4 H.sub.9               1-2 4-Cl, 6-F                         t-butyl      J1533   CH       NC.sub.4 H.sub.9               1-2 4-Cl, 6-F                         CF.sub.3     J1534   CH       NC.sub.4 H.sub.9               1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J1535   CH       NCH.sub.2 OCH.sub.3               1-2 4-Cl, 6-F                         CH.sub.3     J1536   CH       NCH.sub.2 OCH.sub.3               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1537   CH       NCO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         isopropyl    J1538   CH       NCH.sub.2 OCH.sub.3               1-2 4-Cl, 6-F                         t-butyl      J1539   CH       NCH.sub.2 OCH.sub.3               1-2 4-Cl, 6-F                         CF.sub.3     J1540   CH       NCH.sub.2 OCH.sub.3               1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J1541   CH       NCO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         CH.sub.3     J1542   CH       NCO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1543   CH       NCO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         isopropyl    J 1544   CH       NCO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         t-butyl      J1545   CH       NCO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         CF.sub.3     J1546   CH       NCO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J1547   CH       NSO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         CH.sub.3     J1548   CH       NSO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1549   CH       NSO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         isopropyl    J1550   CH       NSO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         t-butyl      J1551   CH       NSO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         CF.sub.3     J1552   CH       NSO.sub.2 CH.sub.3               1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J1553   CH       NCH.sub.2 CHCH.sub.2               1-2 4-Cl, 6-F                         CH.sub.3     J1554   CH       NCH.sub.2 CHCH.sub.2               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1555   CH       NCH.sub.2 CHCH.sub.2               1-2 4-Cl, 6-F                         isopropyl    J1556   CH       NCH.sub.2 CHCH.sub.2               1-2 4-Cl, 6-F                         t-butyl      J1557   CH       NCH.sub.2 CHCH.sub.2               1-2 4-Cl, 6-F                         CF.sub.3     J1558   CH       NCH.sub.2 CHCH.sub.2               1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J1559   CH       NCH.sub.2 C.tbd.CH               1-2 4-Cl, 6-F                         CH.sub.3     J1560   CH       NCH.sub.2 C.tbd.CH               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1561   CH       NCH.sub.2 C.tbd.CH               1-2 4-Cl, 6-F                         isopropyl    J1562   CH       NCH.sub.2 C.tbd.CH               1-2 4-Cl, 6-F                         t-butyl      J1563   CH       NCH.sub.2 C.tbd.CH               1-2 4-Cl, 6-F                         CF.sub.3     J1564   CH       NCH.sub.2 C.tbd.CH               1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J1565   CH       NCH.sub.2 CO.sub.2 Me               1-2 4-Cl, 6-F                         CH.sub.3     J1566   CH       NCH.sub.2 CO.sub.2 Me               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1567   CH       NCH.sub.2 CO.sub.2 Me               1-2 4-Cl, 6-F                         isopropyl    J1568   CH       NCH.sub.2 CO.sub.2 Me               1-2 4-Cl, 6-F                         t-butyl      J1569   CH       NCH.sub.2 CO.sub.2 Me               1-2 4-Cl, 6-F                         CF.sub.3     J1570   CH       NCH.sub.2 CO.sub.2 Me               1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J1571   CH       NCH.sub.2 CHF.sub.2               1-2 4-Cl, 6-F                         CH.sub.3     J1572   CH       NCH.sub.2 CHF.sub.2               1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1573   CH       NCH.sub.2 CHF.sub.2               1-2 4-Cl, 6-F                         isopropyl    J1574   CH       NCH.sub.2 CHF.sub.2               1-2 4-Cl, 6-F                         t-butyl      J1575   CH       NCH.sub.2 CHF.sub.2               1-2 4-Cl, 6-F                         CF.sub.3     J1576   CH       NCH.sub.2 CHF.sub.2               1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J1577   CH       NH      1-2 4-Cl, 6-F                         CH.sub.3     J2578   CH       NH      1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J2579   CH       NH      1-2 4-Cl, 6-F                         isopropyl    J2580   CH       NH      1-2 4-Cl, 6-F                         t-butyl      J2581   CH       NH      1-2 4-Cl, 6-F                         CF.sub.3     J2582   CH       NH      1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J2583   CH       NH      1-2 4-Cl, 6-F                         CH.sub.3     J3584   CH       NH      1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J3585   CH       NH      1-2 4-Cl, 6-F                         isopropyl    J3586   CH       NH      1-2 4-Cl, 6-F                         t-butyl      J3587   CH       NH      1-2 4-Cl, 6-F                         CF.sub.3     J3588   CH       NH      1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J3589   CH       NH      1-2 4-Cl, 6-F                         CH.sub.3     J4590   CH       NH      1-2 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J4591   CH       NH      1-2 4-Cl, 6-F                         isopropyl    J4592   CH       NH      1-2 4-Cl, 6-F                         t-butyl      J4593   CH       NH      1-2 4-Cl, 6-F                         CF.sub.3     J4594   CH       NH      1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J4595   CH       NH      1-2 4-Cl  CO.sub.2 CH.sub.2 CH.sub.3                                      J5596   CH       NH      1-2 4-Cl, 6-F                         CH.sub.3     J5597   CH       NH      1-2 4-Cl, 6-F                         C.sub.2 H.sub.3                                      J5598   CH       NH      1-2 4-Cl, 6-F                         isopropyl    J5599   CH       NH      1-2 4-Cl, 6-F                         t-butyl      J5600   CH       NH      1-2 4-Cl, 6-F                         CF.sub.3     J5601   CH       NH      1-2 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J5602   NH       CH      2-3 4-Cl, 6-F                         CH.sub.3     J7603   NH       CH      2-3 4-Cl, 6-F                         n-C.sub.3 H.sub.7                                      J1604   NH       CH      2-3 4-Cl, 6-F                         i-C.sub.3 H.sub.7                                      J1605   NH       CH      2-3 4-Cl, 6-F                         t-C.sub.4 H.sub.9                                      J1606   NH       CH      2-3 4-Cl, 6-F                         CH.sub.2 OH  J1607   NH       CH      2-3 4-Cl, 6-F                         CH.sub.2 CH.sub.2 OH                                      J1608   NH       CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 OH                                      J1609   NH       CH      2-3 4-Cl, 6-F                         CONHCH.sub.3 J1610   NH       CH      2-3 4-Cl, 6-F                         CON(CH.sub.3).sub.2                                      J1611   NH       CH      2-3 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J1612   NH       CH      2-3 4-Cl, 6-F                         Phenyl       J1613   NH       CH      2-3 4-Cl, 6-F                         CF.sub.2 CF.sub.3                                      J1614   NH       CH      2-3 4-Cl, 6-F                         CH.sub.2 OCH.sub.3                                      J1615   NH       CH      2-3 4-Cl, 6-F                         Benzyl       J1616   NH       CH      2-3 4-Cl, 6-F                         4-chlorophenylmethyl                                      J1617   NH       CH      2-3 4-Cl, 6-F                         SO.sub.2 CH.sub.3                                      J1618   NH       CH      2-3 4-Cl, 6-F                         CF.sub.3     J1619   NH       CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 OCOCH.sub.3                                      J1620   NH       CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 CH.sub.2 OH                                      J1621   NH       CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3                                      J1622   NH       CH      2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1623   NH       CH      2-3 4-Cl, 6-F                         CO.sub.2 Na  J1624   NH       CH      2-3 4-Cl, 6-F                         CONHSO.sub.2 CH.sub.3                                      J1625   NH       CH      2-3 4-Cl, 6-F                         CHFCH.sub.3  J1626   NH       CH      2-3 4-Cl, 6-F                         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                      J1627   NH       CH      2-3 4-Cl, 6-F                         CH.sub.3     J2628   NH       CH      2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J2629   NH       CH      2-3 4-Cl, 6-F                         isopropyl    J2630   NH       CH      2-3 4-Cl, 6-F                         t-butyl      J2631   NH       CH      2-3 4-Cl, 6-F                         CF.sub.3     J2632   NH       CH      2-3 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J2633   NH       CH      2-3 4-Cl, 6-F                         CH.sub.3     J3634   NH       CH      2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J3635   NH       CH      2-3 4-Cl, 6-F                         isopropyl    J3636   NH       CH      2-3 4-Cl, 6-F                         t-butyl      J3637   NH       CH      2-3 4-Cl, 6-F                         CF.sub.3     J3638   NH       CH      2-3 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J3639   NH       CH      2-3 4-Cl, 6-F                         CH.sub.3     J4640   NH       CH      2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J4641   NH       CH      2-3 4-Cl, 6-F                         isopropyl    J4642   NH       CH      2-3 4-Cl, 6-F                         t-butyl      J4643   NH       CH      2-3 4-Cl, 6-F                         CF.sub.3     J4644   NH       CH      2-3 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J4645   NH       CH      2-3 4-Cl, 6-F                         CH.sub.3     J5646   NH       CH      2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J5647   NH       CH      2-3 4-Cl, 6-F                         isopropyl    J5648   NH       CH      2-3 4-Cl, 6-F                         t-butyl      J5649   NH       CH      2-3 4-Cl, 6-F                         CF.sub.3     J5650   NH       CH      2-3 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J5651   NH       CCH.sub.3               2-3 4-Cl, 6-F                         CH.sub.3     J1652   NH       CCH.sub.3               2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1653   NH       CCH.sub.3               2-3 4-Cl, 6-F                         isopropyl    J1654   NH       CCH.sub.3               2-3 4-Cl, 6-F                         t-butyl      J1655   NH       CCH.sub.3               2-3 4-Cl, 6-F                         CF.sub.3     J1656   NH       CCH.sub.3               2-3 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J1657   NH       CCH.sub.2 CH.sub.3               2-3 4-Cl, 6-F                         CH.sub.3     J1658   NH       CCH.sub.2 CH.sub.3               2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1659   NH       CCH.sub.2 CH.sub.3               2-3 4-Cl, 6-F                         isopropyl    J1660   NH       CCH.sub.2 CH.sub.3               2-3 4-Cl, 6-F                         t-butyl      J1661   NH       CCH.sub.2 CH.sub.3               2-3 4-Cl, 6-F                         CF.sub.3     J1662   NH       CCH.sub.2 CH.sub.3               2-3 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J1663   NH       CCH.sub.2 CHF.sub.2               2-3 4-Cl, 6-F                         CH.sub.3     J1664   NH       CCH.sub.2 CHF.sub.2               2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J1665   NH       CCH.sub.2 CHF.sub.2               2-3 4-Cl, 6-F                         isopropyl    J1666   NH       CCH.sub.2 CHF.sub.2               2-3 4-Cl, 6-F                         t-butyl      J1667   NH       CCH.sub.2 CHF.sub.2               2-3 4-Cl, 6-F                         CF.sub.3     J1668   NH       CCH.sub.2 CHF.sub.2               2-3 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J1669   NH       CH      2-3 4-Cl, 6-F                         CH.sub.3     J2670   NH       CH      2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J2671   NH       CH      2-3 4-Cl, 6-F                         isopropyl    J2672   NH       CH      2-3 4-Cl, 6-F                         t-butyl      J2673   NH       CH      2-3 4-Cl, 6-F                         CF.sub.3     J2674   NH       CH      2-3 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J2675   NH       CH      2-3 4-Cl, 6-F                         CH.sub.3     J3676   NH       CH      2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J3677   NH       CH      2-3 4-Cl, 6-F                         isopropyl    J3678   NH       CH      2-3 4-Cl, 6-F                         t-butyl      J3679   NH       CH      2-3 4-Cl, 6-F                         CF.sub.3     J3680   NH       CH      2-3 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J3681   NH       CH      2-3 4-Cl, 6-F                         CH.sub.3     J4682   NH       CH      2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J4683   NH       CH      2-3 4-Cl, 6-F                         isopropyl    J4684   NH       CH      2-3 4-Cl, 6-F                         t-butyl      J4685   NH       CH      2-3 4-Cl, 6-F                         CF.sub.3     J4686   NH       CH      2-3 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J4687   NH       CH      2-3 4-Cl, 6-F                         CH.sub.3     J5688   NH       CH      2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J5689   NH       CH      2-3 4-Cl, 6-F                         isopropyl    J5690   NH       CH      2-3 4-Cl, 6-F                         t-butyl      J5691   NH       CH      2-3 4-Cl, 6-F                         CF.sub.3     J5692   NH       CH      2-3 4-Cl, 6-F                         CO.sub.2 CH.sub.3                                      J5693   NCH.sub.3       CH      2-3 4-Cl, 6-F                         CF.sub.3     J1694   NH       CH      2-3 4-Cl  CF.sub.3     J1695   CH       NH      1-2 4-Cl, 6-F                         CF.sub.3     J1696   CH       NCH.sub.2 C.sub.6 H.sub.5               1-2 4-Cl, 6-F                         CF.sub.3     J1697   CH       NCH.sub.2 CO.sub.2 C.sub.2 H.sub.5               1-2 4-Cl, 6-F                         CF.sub.3     J1698   CH       NCOCH.sub.3               1-2 4-Cl, 6-F                         CF.sub.3     J1699   CH       NCH.sub.2 C.tbd.N               1-2 4-Cl, 6-F                         CF.sub.3     J1700   CH       NH      1-2 4-Cl, 6-F                         CF.sub.3     J1701   CH       NH      1-2 4-Cl, 6-F                         CO.sub.2 C.sub.2 H.sub.5                                      J1702   CH       NH      1-2 4-Cl  CO.sub.2 C.sub.2 H.sub.5                                      J1703   N        O       1-2 4-Cl, 6-F                         CH.sub.3     J7704   O        CH      1-2 4-Cl, 6-F                         C(CH.sub.3).sub.2 OH                                      J7705   NH       N       2-3 4-Cl, 6-F                         CF.sub.3     J6706   NH       N       2-3 4-Cl, 6-F                         C(CH.sub.3).sub.3                                      J6707   NH       N       2-3 4-Cl, 6-F                         CF.sub.3     J7708   NH       N       2-3 4-Cl, 6-F                         CH.sub.2 C(CH.sub.3).sub.3                                      J1709   NH       N       2-3 4-Cl, 6-F                         3,5-dimethylisoxazolyl                                      J1710   NH       N       2-3 4-Cl, 6-F                         pyridin-2-yl J1711   NCOCH.sub.3       N       2-3 4-Cl, 6-F                         H            J1712   NH       N       2-3 4-Cl, 6-F                         C.sub.7 F.sub.15                                      J1713   NH       N       2-3 4-Cl, 6-F                         CHCl.sub.2   J1714   NH       N       2-3 4-Cl, 6-F                         NHCO.sub.2 C.sub.2 H.sub.5                                      J1715   NH       N       2-3 4-Cl, 6-F                         CH(CH.sub.3)NHCH.sub.2 CO.sub.2 C.sub.2                         H.sub.5      J1716   NH       N       2-3 4-Cl, 6-F                         CH(CH.sub.3)OCOCH.sub.3                                      J1717   NH       N       2-3 4-Cl, 6-F                         C(CH.sub.3)═CH.sub.2                                      J1718   NH       N       2-3 4-Cl, 6-F                         CH═C(CH.sub.3).sub.2                                      J1719   NH       N       2-3 4-Cl, 6-F                         CH(Br)CH.sub.3                                      J1720   NH       N       2-3 6-F   CF.sub.3     J1721   NH       N       2-3 4-Cl, 6-F                         CH═NC.sub.6 H.sub.5                                      J1722   NH       N       2-3 4-Cl, 6-F                         CH.sub.2 OCOCH.sub.3                                      J1723   NH       N       2-3 4-Cl, 6-F                         CH(OCH.sub.3)C.sub.6 H.sub.5                                      J1724   NH       N       2-3 4-Cl, 6-F                         CH(OCOCH.sub.3)C.sub.6 H.sub.5                                      J1725   NH       N       2-3 4-Cl, 6-F                         SCH.sub.3    J1726   NH       N       2-3 4-Cl, 6-F                         C.sub.2 H.sub.5                                      J5727   NCH.sub.3       N       2-3 4,6-Cl.sub.2                         CF.sub.3     J1728   N        NCH.sub.3               2-3 4,6-Cl.sub.2                         CF.sub.3     J1729   NH       NH      --  4-Cl, 6-F                         CF.sub.3     J1730   NH       N       2-3 4,6-Cl.sub.2                         CF.sub.3     J5731   NH       N       2-3 4-Cl, 6-F                         SO.sub.2 CH.sub.3                                      J1732   NH       N       2-3 4-Br, 6-F                         CF.sub.3     J1733   NH       N       2-3 4-Br, 6-F                         C.sub.2 H.sub.5                                      J1734   NH       N       2-3 4-Cl, 6-F                         CH.sub.2 OH  J1735   NH       N       2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 OH                                      J1736   NH       N       2-3 4-Cl, 6-F                         C(CH.sub.3)OCH.sub.2 C.sub.6 H.sub.5                                      J1737   NH       N       2-3 4-Cl, 6-F                         SH           J1738   NH       N       2-3 4-Cl, 6-F                         SCH(CH.sub.3)C.tbd.N                                      J1739   NH       N       2-3 4-Cl, 6-F                         SC.sub.2 H.sub.5                                      J1740   NH       N       2-3 4-Cl, 6-F                         SCH.sub.2 C.tbd.CH                                      J1741   NH       N       2-3 4-Cl, 6-F                         SCH.sub.2 C.sub.6 H.sub.5                                      J1742   NH       N       2-3 4-Cl, 6-F                         SC.tbd.N     J1743   NH       N       2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 CH.sub.2 SC.tbd.N                                      J1744   NH       N       2-3 4-Cl, 6-F                         SCH(CH.sub.3)CO.sub.2 C.sub.2 H.sub.5                                      J1745   NH       N       2-3 4-Cl, 6-F                         SCH(CH.sub.3)CON(CH.sub.3).sub.2                                      J1746   NH       N       2-3 4-Cl, 6-F                         SCH.sub.2 C.tbd.CH                                      J5747   NH       N       2-3 4-Cl, 6-F                         SCH.sub.2 C═CH.sub.2                                      J1748   NH       N       2-3 4-Cl, 6-F                         SCH.sub.2 C.tbd.N                                      J1749   NH       N       2-3 4-Cl, 6-F                         SCH.sub.2 C.tbd.CCH.sub.2 Cl                                      J1750   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 OCONHCH.sub.3                                      J1751   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 NHCOCH.sub.2 (C.sub.6 H.sub.4,                                      J1                         2-NO.sub.2)  J1752   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3)(OH)C.sub.6 H.sub.5                                      J1753   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 NH.sub.2                                      J1754   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3)(OH)CH(CH.sub.3).sub.2                                      J1755   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 NHCOCH.sub.3                                      J1756   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 NHSO.sub.2 CH.sub.3                                      J1757   O        CH      2-3 4-Cl, 6-F                         C(CH.sub.3).sub.2 F                                      J1758   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CO.sub.2 H                                      J1759   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CON(CH.sub.3).sub.2                                      J1760   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CON(CH.sub.3)(OCH.sub.3)                                      J1761   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CONHCH.sub.3                                      J1762   O        CH      2-3 4-Cl, 6-F                         CH.sub.2 CONH.sub.2                                      J1763   O        CH      2-3 4-Cl, 6-F                         C.sub.2 H.sub.4 CON(CH.sub.3)(OCH.sub.3)                                      J1764   O        CH      2-3 4-Cl, 6-F                         C.sub.2 H.sub.4 CO.sub.2 CH.sub.3                                      J1765   O        CH      2-3 4-Cl, 6-F                         C.sub.3 H.sub.6 OH                                      J1766   O        CH      2-3 4-Cl, 6-F                         C.sub.2 H.sub.4 CONHCH.sub.3                                      J1767   NH       N       2-3 4-Cl  SCF.sub.3    J1768   NH       N       2-3 4-Cl  CF.sub.3     J1769   NH       N       2-3 4-Cl  CF.sub.3     J3__________________________________________________________________________ 
    
     
                                           TABLE 3__________________________________________________________________________Characterizing DataMelting Points or Physical States of Representative CompoundsNo.   MP/State    No.       MP/State               No.                  MP/State                          No.                             MP/State__________________________________________________________________________ 1 OIL   246       45-9    377                  122-30  722                             117-122 RESIN 16   70-72 247       35-8    378                  200 C&gt;  723                             107-112 RESIN 25   OIL   248        67-71  379                  116-22  724                             108-114 RESIN 26   OIL   249       84-9    380                  201-4   725                             135-140 RESIN 28   OIL   250        65-68  381                  117-24  726                             &gt;210 30   OIL   251       55-7    382                  193-5   727                             182-183 38   246-9 252       OIL     383                  131-40  728                             174-175 42   &gt;250  253       GLASS   384                  103-5   729                             &gt;205 43   SOLID 254       71-5    385                  158-160 730                             &gt;205 49   OIL   255       134-8   386                  132-5   731                             150-152 RESIN 96   OIL   256       145-7   387                  112-4   732                             195-200 98   &gt;245  257       OIL     388                  107-9   733                             &gt;205 99   OIL   258       232-40  399                  177.5-8.5                          734                             SOLID100   OIL   259       165-9   405                    130   735                             118-121 RESIN101   OIL   260       55-8    469                   98-100 736                             88-92102   OIL   261       65-7    481                  SOLID   737                             &gt;200103   OIL   262       75-7    493                  187-8   738                             133-135104   OIL   263       &gt;50     500                  208-10  739                             130-132105   &gt;250  264       155-7   513                  178-181 740                             178-180106   OIL   265       130-6   522                  78-80   741                             118-121 RESIN107   OIL   266       258-61  527                  152-154 742                             150-155108   &gt;250  267       110-8   563                  165-166 743                             SOLID109   OIL   268       73-7    595                  &gt;240    744                             160-162110   OIL   269       270-5   618                    235-237.5                          745                             &gt;200112   86-88 270       265-72  693                  60-65   746                             106-109221   193.5-6    271        62-72  694                  221.5-223                          747                              98-100222   183-6 272       OIL     695                  160-162 748                             104-110 RESIN223   OIL   273        220-2.5               696                  173-177 749                             155-158 RESIN224   OIL   274       116 SOFTENS               697                  60-63   750                             137-139225   OIL   275       OIL     698                    142-145.5                          751                             189-190226   63-6  276       145-53  699                   95-102 752                             78-82227   134-6 277       179-82  700                  160-162 753                             87-89228   42-5  278       189-92  701                  245-248 754                             75-77229   OIL   279       197-8   702                  258-260 755                             96-98230   163-5 280       215-6   705                  102-103 756                             90-92231   65-70 362       152-8   706                  88-89   757                             60-62232   186-91    363       &gt;165    708                  140 DEC 758                             95-97233   85-90 364       SOLID   709                  &gt;200    759                             144-146234   65-70 365       172-7   710                  130 RESIN                          760                             146-147235   63-7  366         130   711                  &gt;200    761                             70-76236   56-8  367       150-5   712                  93-98 RESIN                          762                             185-187237   141-2 368        87-93  713                  123-130 RESIN                          763                             63-65238   143-5 369       125-30  714                  160-165 RESIN                          754                             OIL239   162-4 370         130   715                  90-95   765                             50-54240   72-6  371       SOLID   716                  115-120 RESIN                          766                             172-173241   67-70 372       SOLID   717                  120-125 767                             239-241242   163-5 373         160   718                  110-116243   51-55 374         190   719                  120-125244   OIL   375       &gt;200    720                  128-132 RESIN245   OIL   376       142-8   721                  145-150__________________________________________________________________________ 
    
     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, VolumeRate     Stock Solution               Acetone/Water                            of Spray Solution(g/ha)   (mL)       (mL)         (mL)______________________________________3000     10         35           451000     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 postemergent 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 1000 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 &#34;Research Methods in Weed Science,&#34; 2nd ed., B. Truelove, Ed.; Southern Weed Science Society; Auburn University, Auburn, Ala., 1977. The rating system is as follows: 
     
         ______________________________________Herbicide Rating SystemRating DescriptionPercent  of Main    Crop          WeedControl  Categories Description   Description______________________________________ 0     No effect  No crop       No weed             reduction/injury                           control10                Slight dis-   Very poor weed             coloration or stunting                           control20     Slight     Some discoloration,                           Poor weed  eftect     stunting or   control             stand loss30                Crop injury   Poor to defi-             more pronounced                           cient weed             but not lasting                           control40                Moderate injury,                           Deficient weed             crop usually recovers                           control50     Moderate   Crop injury   Deficient to  effect     more lasting, moderate weed             recovery doubtful                           control60                Lasting crop  Moderate weed             injury, no recovery                           control70                Heavy injury and                           Control some-             stand loss    what less than             satisfactory80     Severe     Crop nearly destroyed                           Satisfactory to             a few survivors                           weed control90                Only occasional                           Very good to             live plants left                           excellent control100    Complete   Complete crop Complete weed  effect     destruction   destruction______________________________________ 
    
     Formulation 
     The 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  65100    40  30     80       100  100  20 --   60   50  70101    80  70    100       100  100 --   80  80  100 100102    20  30     10       100   70 --   50  90  100  60103    50  50     80       100  100 --   70  90  100  70104   100 100    100       100  100 --  100 100  100 100106    30  40     70       100  100  95  60  70   90   55107    80  60     90       100  100 100  40  75  100 100108    0  0  10        70   50  40  10  50   50  30109   100 100     90       100  100 100 100 100  100 100110   100  50     70       100   90 100  40  80  100 100112   100 100    100       100  100 100 100 100  100 100221    70  60     85       100  100  80 ND  ND   100  95222   100  70     90       100  100 100 100 ND   100 100223   100  50     80       100  100 100  90 ND   100 100224   100  80     90       100  100 100  95  80  100 100225    40  20     30        90   50  70  50 ND   100  60226    70  50     70       100   90  90  60 ND   100  80227   100  80     90       100  100 100 ND   95  100 100228   100  80     95       100  100 100  90 ND   100 100229   100  70     90       100  100 100  95  80  100 100230   100  40     80       100  100 100 100  80  100 100231   100  80    100       100  100 100 100  90  100 100232    20  30     50        90   80  20  10 ND    40  25233    40  30     70       100   95  20  20 ND    60  50234   100 100    100       100  100 100 100  80  100 100235   100  90    100       100  100 100 100  80  100 100236   100  70     95       100  100 100 100  80  100 100237   100  90     90       100  100 100 100 100  100 100238   100  60     70       100  100  60  80  50   90  90239   100  70     90       100  100 100 ND  ND   100  90240   100  95     95       100  100 100 100 ND   100 100241    60  70     95       100  100 100 100 ND   100 100242   100 100    100       100  100 100 100 100  100 100243   100  80     95       100  100 100 100 ND   100 100244    95  80    100       100   90  70 100  70  100 100245   100  60     80       100  100  90 100  70  100  80246   100 100    100       100  100 100 100 100  100 100247   100  90     90       100  100  95 100  85  100 100248   100  90     95       100  100 100 100  95  100 100249   100  80     95       100  100 100  90  80   10 100250    80  40     50       100  100 ND  100  60  100  70251    90  90     95       100  100  95 100  90  100 100252   100 100    100       100  100 100 ND  100  100 100253   100 95 100       100  100 100 ND  ND   100 100254    25  20     80       100   50  30  50  60  100  80255   100  90     95       100  100 100 100 ND   100 100256   100  80     95       100  100 100 ND   70  100  90257    40  0  10        90   70  0   20  20   70  10258    30  30     75       100   60  0   60 ND    40  40259    70  40     80       100   70 100  55 ND   100  95260   100  70     80       100  100 100 100  95  100 100261   100  80     95       100  100 100  90  80  100 100262    90  40     40       100  100 100 100  50  100  70263   100  50     65       100  100 100  95  75  100  70264    0  0  10        20   0   20  30  0    10  10265    70  40     80        90  100  20  70 ND    80  60266    50  30     60        40   70  0   0  ND    30  30267    0  10     20        10   10  0   50  50   5   0268    30  30     50       100   95  20  0  ND    60  60269    60  30     80       100  100 100 100  70  100  75270    70  70     90       100  100 ND   60  65  100 100271    80  70     90       100  100 100 100  80  100  90272    20  0  20       100   70 100  20  70   90  60273   100  80     90       100  100 100 100  90  100 100274   100 100     90       100  100  90 100  95  100 100275   100  80    100       100  100 100 100  80  100  95362   100 100    100       100  100 100 100 100  100 100363   100 100    100       100  100 100 100 100  100 100364   100  60     80       100  100 100 100  80  100  80365   ND  30     30       100  100 100 100  60   75  60366    10  10     0  70   20  0   10  0    50  40367   100  95    100       100  100 100 100  90  100 100368   100 100     95       100  100 100 100  95  100 100369   100 100    100       100  100 100 100 100  100 100370   100 100     95       100  100 100 100  90  100 100371   100  95    100       100  100 100 100 100  100 100372   100  90     95       100  100 100 100  80  100  80373   100  70     90       100  100 100 100  70  100  90374    30  0  10       100   95  90  80  40  100  75375    80  30     90       100   80  95  80  80  100  95376    50  60     80       100  100 100 100 100  100  70377   100  70     90       100  100 ND  100 100  100 100378    90  70     90       100  100 100 100  80  100  95379   100  50     70       100  100 ND  100  80  100  95380    80  35     20       100  100 ND   80  90  100  70381   100  40     80       100  100 ND  100  90  100  80382    60  45     30       100   70 ND   60  90   95  80383    80  40     20       100   60 ND   70  80   75  55399    95  80     95       100   95 100  70  60  100  0493    80  70     90       100  100 100  70  75  100 100500    95  75     90       100  100 100 100  75  100 100522    90  40     80       100  100 100  50  75  100 100595    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  65100    85  40     60        90  100  50  50 --    30  40101    95  50     80       100  100 --  --   60   65  65102    80  30     75       100  100 --  --   60   90  60103    90  50     80       100   80 --   80  70  100  60104   100 100    100       100  100 --  --  --   100 100106    80  30     75       100  100 --  --   60  100  70107    95  40    100       100  100 100 --   90  100 100108    50  20     60        20   60  0   10  10   70  20109    90  90     80       100  100 --  100  90  100  90110    80  40     50       100  100 100  70  80   70112   100 100    100       100  100 100 100 100  100 100221    95  50     60       100  100 100  60  40   70  70222   100  70     90       100  100 100 100 100  100 100223    95  40     90       100  100 100 100 ND   100 100224    95  70    100       100  100 100 100  90  100 ND225    60  30     60       100   75 ND   70 ND    90  60226    70  40     80       100   95  80  90 ND   100  80227    95  60     90       100  100 100 100 100  100 100228    90  50     80       100  100  80  95 ND   100  90229    95  60     80       100  100 100 100  70  100 100230    95  40     80       100  100  90 100  70  100  90231   100  70    100       100  100 100 ND  100  100 100232    75  50     30       100   80  20  40 ND    30  10233    90  30     60       100  100  30  30 ND    30  30234   100 100    100       100  100 100 100 100  100 100235   100 100    100       100  100 100 100 100  100 100236   100  75     90       100  100 100 100  80  100 100237   100  95    100       100  100 ND  100 100  100 100238    80  30     70       100  100 ND  100  40   80  70239    95  60     80       100  100 100 100 ND   100  80240    95  95    100       100  100 100 100 ND   100 100241    90  60     70       100  100  85  95 ND   100  70242   100 100    100       100  100 100 100 100  100 100243    95  70     95       100  100 100 100 ND   100 100244    95  60     90       100  100 100 100  75  100 ND245    85  40     75       100  100  60  70  50   70  70246    95 100    100       100  100 100 100 ND   100 100247    95  80    100       100  100 100 100 100  100 ND248    80  50     95       100  100 100 100 ND   100 100249    95  80    100       100  100 100 100 100  100 ND250    95  50     80       100  100  80 100  40  100 100251    95  70     90       100  100 100  95 100  100  95252    95  90    100       100  100 100 ND  100  100 100253    95 100    100       100  100 100 100 ND   100 100254    95  40     80       100   70 ND   95  50  100  80255   100 100    100       100  100 100 100 ND   100 100256   100  80     90       100  100 100 100  80  100 100257    70  20     70       100   60  30  70  30   70  50258    80  30     60        80   70  5   50  30   60  50259    80  35     75       100   90  30  70  55   80  70260    90  80     70       100  100 ND  100  90  100  90261    95  80    100       100  100 100 100 100  100 100262    95  60     80       100  100  95  95  50  100  80263    95  80     90       100  100 100 100  60   90  70264    50  20     50        40   40  0   30  0   ND   20265    70  40     60       100  100  30  20 ND    40  20266    60  40     60        50   60  10  10 ND    40  40267    50  15     50        80   40  10  10  20   30  20268    70  40     60        50   90  20 ND  ND    70  40269    90  40     70       100   80  80 ND  ND    70  60270    70  40     50       100   60  40 ND   50   50  50271    80  40     60       100  100 100 ND  ND    70  50272    50  30     45       100   60  50  50  20   70  40273    95  60     95       100  100  90 100  80  100 100274    95  60     95       100  100  90 100  90  100 100275   100  70     90       100  100 100 100  95  100 100362   100 100    100       100  100 100 ND  100  100 100363   100 100    100       100  100 ND  100 100  100 100364    95  40     80       100  100 100 100 ND   100 100365   100  40     70       100  100 100 ND   70   80  30366    70  30     80        95   80  30 100  30   50  50367   100 100    100       100  100 100 100 100  100 100368   100 100    100       100  100 100 100 100  100 100369   100  80    100       100  100 ND  100 100  100 100370   100  95    100       100  100 100 100 100  100 100371    95 100    100       100  100 100 100 ND   100 100372   100 100    100       100  100 100 100 100  100 100373   100  80    100       100  100 100 100 100  100 100374    80  25     30       100   95  80 100  25   80  60375    95  40     90       100   95 100 100  90   80 100376    90  50     95       100  100 ND  100  90  100 100377    95  80    100       100  100 ND  100 100  100 100378    90  40     90       100   90 ND  100  80  100 100379    95  80    100       100  100 ND  100  70  100 100380    95  30     95       100  100 ND  100  70  100  80381    95  40     95       100  100 ND  100 100  100 100382    80  40    100       100  100 ND  100  80   90  80383    95  40     95       100   95 ND  100  60   95  70399    95  30     70       100  100 100 100  50   70  60493    95  60     90       100  100  80 100  65  100 100500    95  65     95       100  100  90 100  80  100 100522    90  45     90       100  100 100 100  50  100 100595    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 active ingredients 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&#34; 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&#34;); aryloxyalkanoic acids such as (2,4-dichlorophenoxy)acetic acid (-2,4-D&#34;), (4-chloro-2-methylphenoxy)acetic acid (--MCPA&#34;), (+/-)-2-(4-chloro-2-methylphenoxy)propanoic acid (MCPP); ureas such as N,N-dimethyl-N&#39;-[4-(1-methylethyl)phenyl]urea (-isoproturon&#34;); imidazolinones such as 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-pyridinecarboxylic acid (-imazapyr&#34;), a reaction product comprising (+/-)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-4-methylbenzoic acid and (+/-)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-methylbenzoic acid (-imazamethabenz&#34;), (+/-)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-ethyl-3-pyridinecarboxylic acid (-imazethapyr&#34;), and (+/-)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-quinolinecarboxylic acid (-imazaquin&#34;); diphenyl ethers such as 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid (-acifluorfen&#34;), methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate (-bifenox&#34;), and 5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamide (-fomasafen&#34;); hydroxy-benzonitriles such as 4-hydroxy-3,5-diiodobenzonitrile (-ioxynil&#34;) and 3,5-dibromo-4-hydroxybenzonitrile (-bromoxynil&#34;); sulfonylureas such as 2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoic acid (-chlorimuron&#34;), 2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide (-chlorsulfuron&#34;) , 2-[[[[[(4,6- dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]benzoic acid (-bensulfuron&#34;), 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-1-methyl-1H-pyrazol-4-carboxylic acid (-pyrazosulfuron&#34;), 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-2-thiophenecarboxylic acid (-thifensulfuron&#34;), and 2-(2-chloroethoxy)-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide (-triasulfuron&#34;); 2-(4-aryloxyphenoxy)alkanoic acids such as (+/-)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]propanoic acid (-fenoxaprop&#34;), (+/-)-2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid (-fluazifop&#34;), (+/-)-2-[4-(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid (-quizalofop&#34;), and (+/-)-2-[-(2,4-dichlorophenoxy)phenoxy]propanoic acid (-diclofop&#34;); benzothiadiazinones such as 3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide (-bentazone&#34;); 2-chloroacetanilides such as N-butoxymethyl)-2-chloro-2&#39;, 6&#39;-diethylacetanilide (-butachlor&#34;); 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide (-metachlor&#34;), 2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide (-acetochlor&#34;), and (RS)-2-chloro-N-(ethoxymethyl)-N-(2-methoxy-1-methylethyl)acetamide (-dimethenamide&#34;); arenecarboxylic acids such as 3,6-dichloro-2-methoxybenzoic acid (-dicamba&#34;); and pyridyloxyacetic acids such as [(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy]acetic acid (-fluroxypyr&#34;). 
     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.