Abstract:
Substituted N-pyridinyl[1,2,4]triazolo[1,5-c]-pyrimidine-2-sulfonamide compounds, such as N-(2-fluoro-4-methyl)-7-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide, were prepared bycondensation of a 2-chlorosulfonyl[1,2,4]triazolo[1,5-c]pyrimidine compound, such as 2-chlorosulfonyl-7-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine, with a substituted 3-aminopyridine compound, such as 3-amino-2-fluoro-4-methylpyridine, and found to possess herbicidal utility.

Description:
CROSS-REFERENCE TO RELATED APPLICATIONS 
     This application is a Continuation-in-Part of application Ser. No. 08/273,514, filed Jul. 11, 1994, now U.S. Pat. No. 5,461,161. 
    
    
     BACKGROUND OF THE INVENTION 
     The present invention relates to substituted sulfonamide compounds, to herbicidal compositions containing the compounds, and to the utility of the compounds for the control of unwanted vegetation. 
     The control of unwanted vegetation by means of chemical agents, i.e., herbicides, is an important aspect of modern agriculture and land management. While many chemicals that are useful for the control of unwanted vegetation are known, new compounds that are more effective generally, are more effective for specific plant species, are less damaging to desirable vegetation, are safer to man or the environment, are less expensive to use, or have other advantageous attributes are desirable. 
     A number of sulfonamide compounds, including certain substituted [1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide compounds (U.S. Pat. No. 4,954,163) and [1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide compounds (U.S. Pat. No. 5,010,195 and European Application 244,948), are known to possess herbicidal activity, especially on broadleaf weeds. 
     SUMMARY OF THE INVENTION 
     It has now been found that certain N-pyridinyl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide compounds are potent herbicides for the control of unwanted vegetation, have desirable crop selectivity, and have favorable toxicological and environmental attributes. The compounds are effective on grassy as well as broadleaf weeds. 
     The invention includes N-pyridinyl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide compounds of Formula I: ##STR1## wherein 
     R represents CH 2  CF 3  or (C 1  -C 3 )alkyl optionally monosubstituted with F, Cl, or OCH 3  ; 
     Y and Z each independently represents H, F, Cl, Br, in, OCH 3 , OC 2  H 5 , C 2  H 5  or CH 3  optionally mono to completely substituted with F; 
     V represents H, COR&#39;, CO 2  R&#34;, or CONR&#34;&#39; 2  ; 
     A and B each independently represents H, R&#39;, OR&#39;, OCH 2  CH 2  Cl, OCH 2  CH 2  OCH 3 , S(O) n  R&#39;, P, Cl, Br, I, CN, NO 2 , C 6  H 5 , CO 2  R&#34;, or CONR&#39;&#34; 2  with the proviso that not more than one of A and B represents H; 
     D represents H, F, Cl, Br, I, CF 3 , or CH 3  ; 
     n represents 0, 1, or 2; 
     R&#39;represents (C 1  -C 4 )alkyl optionally singly to completely substituted with fluorine; 
     R&#34; represents (C 1  -C 4 )alkyl, (C 3  -C 4 )alkenyl, or (C 3  -C 4 ) alkynyl, 
     R&#34;&#39; represents H or (C 1  -C 4 ) alkyl; and when V represents H, the agriculturally acceptable salts thereof. 
     The compounds of the invention, usually in the form of an herbicidal composition containing one or more of them in admixture with an agriculturally acceptable adjuvant or carrier, exhibit strong herbicidal properties when applied either directly to the unwanted vegetation or to the locus thereof and when applied either preemergence or postemergence. 
    
    
     DETAILED DESCRIPTION OF THE INVENTION 
     The N-pyridinyl[1,2,4]triazolo[1,5-c]-myrimidine-2-sulfonamide compounds of the invention can be characterized as [1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide compounds possessing an alkoxy substituent in the 5-position, alkyl, substituted alkyl, alkoxy, or halogen substituents in either or both of the 7- and 8-positions, and a substituted 3-pyridinyl moiety on the sulfonamide nitrogen atom. They are amides derived from a substituted [1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonic acid compound and a substituted 3-aminopyridine compound. 
     The compounds of the invention include those of Formula I: ##STR2## wherein R represents methyl, ethyl, propyl, 1-methylethyl, or cyclopropyl, each optionally monosubstituted with fluorine, chlorine or methoxy or represents 2,2,2-trifluoroethyl. Methyl and ethyl are typically preferred. 
     The Y and Z substituents of Formula I are independently selected and include hydrogen, methyl optionally mono to completely substituted with fluorine, or ethyl, fluoro, chloro, bromo, iodo, methoxy, or ethoxy. The substituents H, CH 3 , F, Cl, Br, I, and OCH 3  are typically preferred and compounds wherein one of Y and Z represents F, Cl, Br, I, CH 3 , or OCH 3  and the other represents H are often more preferred. Compounds wherein R represents methyl or ethyl, Y represents methyl, and Z represents hydrogen or wherein R represents methyl or ethyl, Y represents hydrogen, and Z represents a halogen or methoxy are often of special interest. 
     The term V in Formula I generally represents hydrogen, CO(C 1  -C 4 )alkyl optionally singly to completely substituted with fluorine, CO 2  (C 1  -C 4 )alkyl, CO 2  (C 3  -C 4 )alkenyl, CO 2  (C 3  -C 4 )alkynyl, CONH 2 , CONH(C 1  -C 4 )alkyl, or CON((C 1  -C 4 )alkyl) 2 . Hydrogen is typically preferred. 
     Substituents A and B on the pyridine ring of the compounds of Formula I independently represent hydrogen, fluoro, chloro, bromo, iodo, cyano, nitro, phenyl, 2-chloroethyl, 2-methoxyethyl, CO 2  (C 1  -C 4 )alkyl, CO 2  (C 3  -C 4 ) alkenyl, or CO 2  (C 3  -C 4 )alkynyl, CONH 2 , CONH(C 1  -C 4 )alkyl, or CON((C 1  -C 4 )alkyl) 2, or represent (C 1  -C 4 )alkyl, (C 1  -C 4 )alkoxy, (C 1  -C 4 )alkylthio, (C 1  -C 4 )alkylsulfinyl, or (C 1  -C 4 ) alkylsulfonyl each optionally singly to completely substituted with fluorine, provided that at least one of A and B represents a substituent other than hydrogen. It is usually preferable that A and B both represent a substituent other than hydrogen. Methyl, ethyl, hydrogen, methoxy, ethoxy, propoxy, 1-methylethoxy, 1-methyl-2,2,2-trifluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, methoxycarbonyl, ethoxycarbonyl, fluoro, chloro, and bromo are often preferred substituents. The term D represents hydrogen, fluoro, chloro, bromo, iodo, trifluoromethyl, or methyl. It is often preferably hydrogen or methyl and is usually more preferably hydrogen. Compounds wherein A represents CH 3 , O(C 1  -C 3 )alkyl, F, Cl, Br, or I; B represents F, Cl, Br, I, CH 3 , C 2  H 5 , CF 3 , O(C 1  -C 3 )alkyl, OCH(CH 3 )CF 3 , OCH 2  CH 2  F, OCH 2  CHF 2 , or CO 2  (C 1  -C 3 )alkyl; and D represents H are often preferred. Compounds wherein A represents Br, Cl, F, or OCH 3 , B represents CH 3 , OCH 3 , OC 2  H 5 , OC 3  H 7  (n), OC 3  H 7  (i), OCH(CH 3 )CF 3 , or OCH 2  CH 2  F, and D represents H; or wherein A represents OCH 3  or OC 2  H 5 , B represents CO 2  (C 1  -C 2 )alkyl, Br, Cl, or F, and D represents H are sometimes of special interest. 
     When V represents hydrogen, the compounds of Formula I are acidic and the invention includes the agriculturally acceptable salts. 
     The term alkyl as used herein includes straight chain, branched chain, and cyclic moieties. Thus, typical alkyl groups are methyl, ethyl, 1-methylethyl, propyl, cyclopropyl and the like. Methyl and ethyl are often preferred. Typical alkyl groups singly to completely substituted with fluorine include trifluoromethyl, monofluoromethyl, 2,2,2-trifluoroethyl, 2,3-difluoropropyl, and the like; trifluoromethyl is often preferred. Typical alkyl groups monosubstituted with methoxy or chloro include 2-chloroethyl, methoxymemhyl, and 2-methoxy-1-methylethyl. 
     The term &#34;agriculturally acceptable salts&#34; is employed herein to denote compounds wherein the acidic sulfonamide proton of the compound of Formula I is replaced by a cation which itself is neither herbicidal to crop plants being treated nor significantly deleterious to the applicator, the environment, or the ultimate user of any crop being treated. Suitable cations include, for example, those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Preferred cations include sodium, potassium, magnesium, and aminium cations of the formula: 
     
         R.sup.6 R.sup.7 R.sup.8 NH.sup.⊕ 
    
     wherein R 6 , R 7 , and R 8  each, independently represents hydrogen or (C 1  -C 12 )alkyl, (C 3  -C 12 )cycloalkyl, or (C 3  -C 12 )alkenyl, each of which is optionally substituted by one or more hydroxy, (C 1  -C 8 )alkoxy, (C 1  -C 8 )alkylthio or phenyl groups; provided that R 6 , R 7 , and R 8  are sterically compatible. Additionally, any two of R 6 , R 7 , and R 8  together may represent an aliphatic difunctional moiety containing 1 to 12 carbon atoms and up to two oxygen or sulfur atoms. Salts of the compounds of Formula I can be prepared by treatment of compounds of Formula I wherein V represents hydrogen with a metal hydroxide, such as sodium hydroxide, potassium hydroxide, or magnesium hydroxide, or an amine, such as ammonia, trimethylamine, hydroxyethylamine, bisallylamine, 2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine. 
     A listing of some typical compounds of the invention is given in Table 1. Some of the specifically preferred compounds of the invention include the following: N-(2-fluoro-4-methyl-3-pyridinyl)-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide, N-(2-chloro-4-methoxy-3-pyridinyl)-5-methoxy-7-methyl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide, N-(2-methoxy-4-methyl-3-pyridinyl)-7-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide, N-(2-chloro-4-methoxy-3-pyridinyl)-7-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide, N-(2-chloro-4-methyl-3-pyridinyl)-8-iodo-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide, N-(2-chloro-4-methyl-3-pyridinyl)-8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide, N-(2-chloro-4-methoxy-3-pyridinyl)-7-chloro-5-ethoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide, N-(2-chloro-4-methyl-3-pyridinyl)-5-methoxy-8-chloro[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide, N-(2-chloro-4-methoxy-3-pyridinyl)-5-ethoxy-7-methyl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide, and N-(2-chloro-4-(1-methylethoxy-3-pyridinyl)-5-ethoxy-7-methyl[1,2,4]triazolo [1,5-c]pyrimidine-2-sulfonamide. 
     
                                           TABLE 1__________________________________________________________________________N-PYRIDINYL[1,2,4]TRIAZOLO[1,5-C]PYRIMIDINE-2-SULFONAMIDE COMPOUNDS ##STR3##                                          % C % H % N % SCpd.                                      Melting                                          calc.                                              calc.                                                  calc.                                                      calc.No. R    Y     Z   A    B       D  Form   point, °C.                                          found                                              found                                                  found                                                      found__________________________________________________________________________ 1  C.sub.2 H.sub.5    H     OCH.sub.3              Cl   H       H  white  225-226                                          40.6                                              3.41                                                  21.8                                                      8.33                              powder      40.3                                              3.61                                                  21.5                                                      8.12 2  C.sub.2 H.sub.5    F     H   Cl   H       H  white  193-194                                          38.6                                              2.70                                                  22.5                                                      8.60                              crystals                                     (d)  38.7                                              2.69                                                  22.4                                                      8.73 3  CH.sub.3    H     OCH.sub.3              CO.sub.2 CH.sub.3                   H       H  white  187-189                                          42.6                                              3.58                                                  21.3                                                      8.13                              powder      42.4                                              3.53                                                  21.3                                                      8.11 4  CH.sub.3    H     I   Cl   H       H  solid  197-200                                          25.4                                              1.38                                                  17.4                                                      7.97                                     (d)  26.0                                              1.30                                                  17.3                                                      7.50 5  CH.sub.3    H     I   CO.sub.2 CH.sub.3                   H       H  pale yellow                                     183-186                                          31.9                                              2.26                                                  17.1                                                      6.54                              powder (d)  32.2                                              2.28                                                  17.2                                                      6.79 6  C.sub.2 H.sub.5    F     H   CO.sub.2 CH.sub.3                   H       H  white  182-183                                          42.4                                              3.31                                                  21.2                                                      8.09                              powder      42.4                                              3.35                                                  21.2                                                      7.94 7  CH.sub.3    CH.sub.3          H   CO.sub.2 CH.sub.3                   H       H  white  181-182                                          44.4                                              3.72                                                  22.2                                                      8.47                              powder      44.7                                              3.68                                                  22.5                                                      8.12 8  CH.sub.3    H     OCH.sub.3              H    CO.sub.2 CH.sub.3                           H  dihyrate                                     &gt;300(d)                                          39.0                                              4.22                                                  19.5                                                      7.45                              yellow      38.8                                              3.52                                                  19.3                                                      6.97                              powder 9  C.sub.2 H.sub.5    F     H   H    CO.sub.2 CH.sub.3                           H  white  141-143                                          42.4                                              3.30                                                  21.2                                                      8.09                              powder      42.3                                              3.43                                                  21.0                                                      7.8710  C.sub.2 H.sub.5    F     H   Cl   CO.sub.2 CH.sub.3                           H  tan powder                                     191-192                                          39.0                                              2.80                                                  19.5                                                      7.44                                     (d)  39.1                                              3.00                                                  18.7                                                      6.7811  CH.sub.3    H     OCH.sub.3              Cl   CO.sub.2 CH.sub.3                           H  tan powder                                     214-216                                          39.2                                              3.06                                                  19.6                                                      7.48                                     (d)  39.5                                              2.97                                                  19.7                                                      7.2812  CH.sub.3    H     I   Cl   CO.sub.2 CH.sub.3                           H  white  193-194                                          29.8                                              1.92                                                  16.0                                                      6.11                              powder (d)  30.2                                              1.83                                                  16.2                                                      6.0613  CH.sub.3    H     OCH.sub.3              Cl   CH.sub.3                           H  off-white                                     196-199                                          40.5                                              3.40                                                  21.8                                                      8.32                              solid  (d)  40.6                                              3.62                                                  21.9                                                      8.1114  C.sub.2 H.sub.5    F     H   Cl   CH.sub.3                           H  white solid                                     177-179                                          40.4                                              3.13                                                  21.7                                                      8.29                                     (d)  40.6                                              3.20                                                  21.7                                                      8.0315  CH.sub.3    H     OCH.sub.3              F    CH.sub.3                           H  white  217-218                                          42.3                                              3.55                                                  22.8                                                      8.68                              powder (d)  42.5                                              3.50                                                  22.6                                                      8.8416  CH.sub.3    H     I   Cl   CH.sub.3                           H  white  203-205                                          30.0                                              2.10                                                  17.5                                                      6.67                              powder      30.2                                              2.13                                                  17.1                                                      6.3917  CH.sub.3    H     CH.sub.3              Cl   CH.sub.3                           H  pale yellow                                     207-208                                          42.3                                              3.55                                                  22.8                                                      8.69                              powder (d)  42.2                                              3.40                                                  22.5                                                      8.4218  CH.sub.3    Cl    H   Cl   CH.sub.3                           H  pale yellow                                     193-194                                          37.0                                              2.59                                                  21.6                                                      8.23                              powder (d)  37.1                                              2.44                                                  21.3                                                      8.1419  CH.sub.3    H     Cl  Cl   CH.sub.3                           H  white  212-214                                          37.0                                              2.59                                                  21.6                                                      8.23                              powder (d)  37.2                                              2.46                                                  21.6                                                      8.0120  C.sub.2 H.sub.5    F     H   F    CH.sub.3                           H  white  188-189                                          42.2                                              3.27                                                  22.7                                                      8.66                              powder (d)  42.4                                              3.33                                                  22.6                                                      8.8321  CH.sub.3    CH.sub.3          H   Cl   CH.sub.3                           H  white  200-201                                          42.3                                              3.55                                                  22.8                                                      8.69                              powder (d)  42.4                                              3.42                                                  22.5                                                      8.7922  CH.sub.3    H     F   Cl   CH.sub.3                           H  white  203-204                                          38.7                                              2.70                                                  22.5                                                      8.60                              powder (d)  38.7                                              2.72                                                  22.3                                                      8.6823  CH.sub.3    H     H   Cl   CH.sub.3                           H  white  199-201                                          40.6                                              3.13                                                  23.7                                                      9.04                              powder (d)  40.6                                              3.12                                                  23.5                                                      8.7824  CH.sub.3    H     Cl  F    CH.sub.3                           H  white  204-205                                          38.7                                              2.90                                                  22.5                                                      8.60                              powder (d)  38.5                                              3.12                                                  22.4                                                      8.2925  CH.sub.3    Cl    H   F    CH.sub.3                           H  white  182-183                                          38.7                                              2.90                                                  22.5                                                      8.60                              powder (d)  38.6                                              2.70                                                  22.3                                                      8.4926  CH.sub.3    H     F   F    CH.sub.3                           H  tan powder                                     190-192                                          40.4                                              2.83                                                  23.6                                                      9.00                                     (d)  40.4                                              3.15                                                  23.6                                                      8.7527  CH.sub.3    CH.sub.3          H   F    CH.sub.3                           H  white  194-195                                          44.3                                              3.72                                                  23.9                                                      9.10                              powder (d)  44.4                                              3.74                                                  24.1                                                      9.2728  CH.sub.3    H     OCH.sub.3              Cl   OCH.sub.3                           H  white  196-197                                          39.0                                              3.27                                                  21.0                                                      8.00                              powder (d)  39.2                                              3.34                                                  20.8                                                      7.9029  CH.sub.3    H     I   F    CH.sub.3                           H  white  194-196                                          30.9                                              2.16                                                  18.0                                                      6.86                              powder (d)  31.0                                              2.36                                                  18.0                                                      6.6030  C.sub.2 H.sub.5    F     H   Cl   OCH.sub.3                           H  white  176-178                                          38.8                                              3.00                                                  20.9                                                      7.96                              powder (d)  38.6                                              2.95                                                  20.8                                                      7.9031  CH.sub.3    H     OCH.sub.3              Cl   Cl      H  white  215-216                                          35.6                                              2.49                                                  20.7                                                      7.91                              powder (d)  35.6                                              2.75                                                  20.5                                                      7.6232  C.sub.2 H.sub.5    F     H   Cl   Cl      H  white  196-197                                          35.4                                              2.23                                                  20.6                                                      7.87                              powder (d)  35.6                                              2.61                                                  20.3                                                      7.4533  CH.sub.3    H     CH.sub.3              F    CH.sub.3                           H  white  206-207                                          44.3                                              3.72                                                  23.9                                                      9.10                              powder (d)  44.5                                              3.58                                                  24.1                                                      9.3834  CH.sub.3    H     H   F    CH.sub.3                           H  white  194-195                                          42.6                                              3.28                                                  24.8                                                      9.48                              powder (d)  42.6                                              3.39                                                  24.8                                                      9.8335  CH.sub.3    CH.sub.3          H   Cl   OCH.sub.3                           H  white solid                                     195-196                                          40.6                                              3.41                                                  21.8                                                      8.33                                     (d)  40.8                                              3.59                                                  21.7                                                      8.0836  CH.sub.3    F     H   OCH.sub.3                   CH.sub.3                           H  white  177-178                                          42.4                                              3.56                                                  22.4                                                      8.70                              powder (d)  42.3                                              3.64                                                  22.8                                                      7.9237  CH.sub.3    H     OCH.sub.3              OCH.sub.3                   CH.sub.3                           H  white  192-193                                          44.2                                              4.24                                                  22.1                                                      8.43                              powder      44.2                                              4.41                                                  22.1                                                      8.4338  CH.sub.3    F     H   Cl   CH.sub.3                           H  white  170-175                                          38.7                                              2.70                                                  22.6                                                      8.60                              powder (d)  38.8                                              2.76                                                  21.3                                                      7.9339  CH.sub.3    H     I   OCH.sub.3                   CH.sub.3                           H  white  195-197                                          32.8                                              2.75                                                  17.7                                                      6.73                              powder (d)  33.1                                              2.67                                                  17.4                                                      6.7840  CH.sub.3    H     OCH.sub.3              Br   CH.sub.3                           H  tan powder                                     187-190                                          36.4                                              3.05                                                  19.6                                                      7.47                                     (d)  36.7                                              3.18                                                  19.4                                                      7.8341  CH.sub.3    F     H   Br   CH.sub.3                           H  white  180-182                                          34.6                                              2.42                                                  20.1                                                      7.68                              powder (d)  34.7                                              2.57                                                  20.1                                                      7.8242  CH.sub.3    CH.sub.3          H   Br   CH.sub.3                           H  white  183-185                                          37.8                                              3.17                                                  20.3                                                      7.76                              powder (d)  38.0                                              3.56                                                  19.9                                                      8.0543  CH.sub.3    H     OCH.sub.3              SC.sub.2 H.sub.5                   CH.sub.3                           H  light yellow                                     176-178                                          43.9                                              4.42                                                  20.5                                                      15.6                              powder (d)  43.7                                              4.51                                                  20.0                                                      14.944  CH.sub.3    F     H   SC.sub.2 H.sub.5                   CH.sub.3                           H  light gray                                     170-172                                          42.2                                              3.79                                                  21.1                                                      16.1                              powder (d)  42.5                                              3.94                                                  20.9                                                      15.845  CH.sub.3    F     H   F    CH.sub.3                           H  white  190-192                                          40.5                                              2.83                                                  23.6                                                      9.00                              powder      40.5                                              2.53                                                  23.5                                                      9.0946  CH.sub.3    OCH.sub.3          H   F    CH.sub.3                           H  white  204-205                                          42.4                                              3.56                                                  22.8                                                      8.70                              powder (d)  42.3                                              3.67                                                  22.6                                                      8.9447  CH.sub.3    Cl    H   Cl   OCH.sub.3                           H  white  183-185                                          35.6                                              2.49                                                  20.7                                                      7.91                              powder (d)  35.6                                              2.31                                                  20.4                                                      7.9248  CH.sub.3    H     Cl  Cl   CH.sub.3                           H  white  194-195                                          35.6                                              2.49                                                  20.7                                                      7.91                              powder (d)  35.7                                              2.38                                                  20.5                                                      7.8949  C.sub.2 H.sub.5    Cl    H   Cl   CH.sub.3                           H  tan powder                                     188-189                                          38.7                                              3.00                                                  20.8                                                      7.95                                     (d)  38.8                                              2.93                                                  20.7                                                      7.9450  C.sub.2 H.sub.5    Cl    H   F    CH.sub.3                           H  tan powder                                     195-196                                          40.4                                              3.13                                                  21.7                                                      8.29                                     (d)  40.5                                              3.04                                                  21.7                                                      8.5351  C.sub.2 H.sub.5    CH.sub.3          H   Cl   OCH.sub.3                           H  white solid                                     194-195                                          42.2                                              3.79                                                  21.1                                                      8.04                                          42.4                                              4.02                                                  19.9                                                      8.0352  CH.sub.3    H     Br  F    CH.sub.3                           H  tan powder                                     189-191                                          34.6                                              2.42                                                  20.1                                                      7.68                                     (d)  34.9                                              2.83                                                  19.9                                                      7.9653  C.sub.2 H.sub.5    CH.sub.3          H   F    CH.sub.3                           H  white  210-211                                          45.9                                              4.13                                                  22.9                                                      8.75                              powder (d)  46.1                                              4.17                                                  23.1                                                      8.9454  C.sub.2 H.sub.5    H     F   F    CH.sub.3                           H  white  204-205                                          42.2                                              3.27                                                  22.7                                                      8.66                              powder (d)  42.2                                              2.87                                                  22.4                                                      8.7755  C.sub.2 H.sub.5    H     F   Cl   CH.sub.3                           H  white  216-217                                          40.4                                              3.13                                                  21.7                                                      8.29                              powder (d)  40.5                                              2.97                                                  21.7                                                      8.1156  C.sub.2 H.sub.5    H     F   Cl   OCH.sub.3                           H  white  205-207                                          38.8                                              3.00                                                  20.9                                                      7.96                              powder (d)  39.0                                              2.96                                                  20.8                                                      8.0657  CH.sub.3    F     H   Cl   OCH.sub.3                           H  white  187-189                                          37.1                                              2.59                                                  21.6                                                      8.25                              powder (d)  37.3                                              2.46                                                  21.5                                                      8.2258  CH.sub.3    OCH.sub.3          H   Cl   OCH.sub.3                           H  tan    197-199                                          39.0                                              3.27                                                  21.0                              solid  (d)  38.9                                              3.40                                                  20.959  CH.sub.3    H     CH.sub.3              Cl   OCH.sub.3                           H  tan    197-198                                          40.6                                              3.41                                                  21.8                              solid  (d)  40.4                                              3.42                                                  21.160  CH.sub.3    CH.sub.2 --          H   F    CH.sub.3                           H  white  199-200                                          44.0                                              3.95                                                  22.0                                                      8.38    OCH.sub.3                 powder (d)  43.9                                              3.92                                                  21.8                                                      8.5061  CH.sub.3    H     F   Cl   OCH.sub.3                           H  white  185-190                                          37.1                                              2.59                                                  21.6                                                      8.25                              powder (d)  37.1                                              2.38                                                  21.4                                                      8.2562  CH.sub.3    SCH.sub.3          H   Cl   OCH.sub.3                           H  white  185-186                                          37.5                                              3.14                                                  20.2                                                      15.4                              powder (d)  37.5                                              3.26                                                  20.2                                                      15.263  C.sub.2 H.sub.5    Cl    H   Cl   OCH.sub.3                           H  white  183-184                                          37.2                                              2.89                                                  20.0                                                      7.65                              powder (d)  37.5                                              2.72                                                  19.8                                                      7.8864  CH.sub.3    F     H   F    H       CH.sub.3                              white  178-179                                          40.5                                              2.83                                                  23.6                                                      9.00                              powder (d)  40.3                                              2.93                                                  23.4                                                      9.2565  CH.sub.3    CH.sub.3          H   F    CH.sub.3                           H  white  191-192                                          44.3                                              3.72                                                  23.9                                                      9.10                              powder (d)  44.2                                              3.82                                                  23.9                                                      9.3666  CH.sub.3    H     OCH.sub.3              F    H       CH.sub.3                              white solid                                     174-176                                     (d)67  CH.sub.3    H     OCH.sub.3              H    CF.sub.3                           H  light yellow                                     221-222                                          38.6                                              2.74                                                  20.8                                                      7.93                              solid       38.5                                              2.63                                                  20.5                                                      7.7668  CH.sub.3    CH.sub.3          H   H    CF.sub.3                           H  white  193-194                                          40.2                                              2.86                                                  21.6                                                      8.26                              powder      40.0                                              2.66                                                  21.7                                                      8.4369  CH.sub.3    CH.sub.3          H   H    CO.sub.2 CH.sub.3                           H  white  156-157                                          44.4                                              3.73                                                  22.2                                                      8.47                              powder      44.6                                              3.59                                                  22.1                                                      8.5870  C.sub.2 H.sub.5    F     H   F    H       Cl tan powder                                     193-194                                          36.9                                              2.32                                                  21.5                                                      8.20                                     (d)  37.1                                              2.43                                                  21.4                                                      7.9871  CH.sub.3    CH.sub.3          H   F    H       Cl white  205-206                                          38.7                                              2.70                                                  22.6                                                      8.60                              powder (d)  38.5                                              2.57                                                  22.5                                                      8.6072  C.sub.2 H.sub.4 Cl    CH.sub.3          H   F    CH.sub.3                           H  tan powder                                     180-18473  CH.sub.2 CF.sub.3    CH.sub.3          H   F    CH.sub.3                           H  white  215-218                                          40.0                                              2.88                                                  20.0                                                      7.63                              powder      40.1                                              2.66                                                  19.8                                                      7.4574  CH.sub.3    CH.sub.3          H   H    CH.sub.3                           H  white solid                                     188-190                                          46.7                                              4.22                                                  25.1                                                      9.59                                          46.8                                              4.06                                                  24.9                                                      9.8775  C.sub.2 H.sub.5    CH.sub.3          H   H    CO.sub.2 CH.sub.3                           H  white  180-181                                          45.9                                              4.11                                                  21.4                                                      8.17                              powder      46.2                                              4.01                                                  21.6                                                      8.3476  C.sub.2 H.sub.5    F     H   H    CH.sub.3                           H  white  161-163                                          44.3                                              3.72                                                  23.9                                                      9.10                              powder      44.4                                              4.09                                                  23.6                                                      8.9377  CH.sub.3    F     OCH.sub.3              F    CH.sub.3                           H  tan    177-180                                          40.4                                              3.13                                                  21.8                                                      8.30                              solid       40.7                                              3.61                                                  21.1                                                      8.0578  CH.sub.3    CH.sub.3          H   OCH.sub.3                   CH.sub.3                           H  white solid                                     215-216                                          46.2                                              4.43                                                  23.1                                                      8.80                                          46.3                                              4.56                                                  23.2                                                      8.3679  CH.sub.3    CH.sub.3          H   H    CO.sub.2 C.sub.2 H.sub.5                           H  white solid                                     152-153                                          45.9                                              4.12                                                  21.4                                                      8.17                                          45.5                                              4.24                                                  21.5                                                      8.1280  CH.sub.3    CH.sub.3          H   Cl   Cl      H  white solid                                     195-196                                          37.0                                              2.59                                                  21.6                                                      8.24                                     (d)  40.8                                              3.13                                                  21.8                                                      7.7681  CH.sub.3    CH.sub.3          H   Cl   OC.sub.2 H.sub.5                           H  white solid                                     202-203                                          42.2                                              3.79                                                  21.1                                                      8.04                                          42.4                                              3.38                                                  21.1                                                      7.7282  CH.sub.3    F     H   Cl   OC.sub.2 H.sub.5                           H  white solid                                     156-157                                          40.3                                              3.39                                                  20.2                                                      7.69                                          40.4                                              3.65                                                  20.0                                                      7.7883  CH.sub.3    CH.sub.3          H   H    CO.sub.2 --                           H  white solid                                     158-159                                          47.3                                              4.46                                                  20.7                                                      7.89                   C.sub.3 H.sub.7 (i)    47.5                                              4.84                                                  20.7                                                      7.4684  CH.sub.3    CH.sub.3          H   H    OC.sub.2 H.sub.5                           H  white solid                                     184-186                                          46.2                                              4.43                                                  23.1                                                      8.08                                          46.5                                              4.37                                                  22.8                                                      7.9885  C.sub.2 H.sub.5    F     H   H    CO.sub.2 --                           H  white solid                                     168-169                                          45.3                                              4.04                                                  19.8                                                      7.55                   C.sub.3 H.sub.7 (i)    45.5                                              4.20                                                  19.6                                                      7.4886  CH.sub.3    CH.sub.3          H   H    Cl      H  white solid                                     218-223                                          47.3                                              3.64                                                  20.3                                                      7.73                                     (d)  47.5                                              3.50                                                  20.1                                                      7.4387  CH.sub.3    H     OCH.sub.3              F    C.sub.2 H.sub.5                           H  white solid                                     191-192                                          44.0                                              3.95                                                  22.0                                                      8.38                                     (d)  43.8                                              3.73                                                  22.0                                                      8.5788  C.sub.2 H.sub.5    F     H   F    C.sub.2 H.sub.5                           H  white solid                                     192-193                                          43.8                                              3.67                                                  21.9                                                      8.34                                     (d)  43.8                                              3.57                                                  21.8                                                      8.5789  CH.sub.3    CH.sub.3          H   F    C.sub.2 H.sub.5                           H  white solid                                     208-209                                          45.9                                              4.13                                                  22.9                                                      8.76                                          45.7                                              4.40                                                  22.8                                                      8.7690  CH.sub.3    CH.sub.3          H   Cl   OC.sub.3 H.sub.7 (n)                           H  white solid                                     175-176                                          43.6                                              4.15                                                  20.3                                                      7.77                                          44.0                                              4.20                                                  20.4                                                      7.4591  CH.sub.3    CH.sub.3          H   Cl   OC.sub.3 H.sub.7 (i)                           H  white solid                                     199-200                                          43.6                                              4.15                                                  20.4                                                      7.77                                          43.5                                              4.11                                                  20.5                                                      7.3992  C.sub.2 H.sub.5    F     H   Cl   OC.sub.3 H.sub.7 (n)                           H  tan solid                                     159-160                                          41.8                                              3.74                                                  19.5                                                      7.44                                     (d)  41.9                                              3.83                                                  19.4                                                      7.7293  C.sub.2 H.sub.5    F     H   Cl   OC.sub.3 H.sub.7 (i)                           H  white solid                                     181-182                                          41.8                                              3.74                                                  19.5                                                      7.44                                     (d)  41.6                                              3.96                                                  18.9                                                      7.5894  CH.sub.3    CH.sub.3          H   F    C.sub.3 H.sub.7 (i)                           H  white solid                                     199-200                                          47.4                                              4.50                                                  22.1                                                      8.43                                     (d)  47.4                                              4.61                                                  21.9                                                      8.3295  CH.sub.3    F     H   Cl   OC.sub.3 H.sub.7 (i)                           H  white solid                                     109-211                                          40.3                                              3.39                                                  20.2                                                      7.69                                     (d)  39.9                                              3.57                                                  19.9                                                      7.4296  C.sub.2 H.sub.5    CH.sub.3          H   F    OC.sub.3 H.sub.7 (i)                           H  white solid                                     212-213                                          45.0                                              4.49                                                  19.7                                                      7.51                                     (d)  44.9                                              4.40                                                  19.5                                                      6.6597  C.sub.2 H.sub.5    F     H   Cl   Cl      Cl white solid                                     218-219                                          32.6                                              1.83                                                  19.0                                                      7.26                                     (d)  33.0                                              1.96                                                  19.1                                                      7.1498  CH.sub.3    CH.sub.3          H   Cl   Cl      Cl white solid                                     200-202                                          34.0                                              2.14                                                  19.8                                                      7.57                                     (d)  34.3                                              1.91                                                  19.7                                                      7.4399  CH.sub.3    H     Br  Cl   OC.sub.2 H.sub.5                           H  white solid                                     174-175                                          33.7                                              2.61                                                  18.1                                                      6.91                                     (d)  33.8                                              2.67                                                  17.9                                                      7.03100 CH.sub.3    H     Br  Cl   OCH.sub.3                           H  white solid                                     194-197                                          32.1                                              2.24                                                  18.7                                                      7.13                                     (d)  32.2                                              2.30                                                  18.8                                                      7.00101 C.sub.2 H.sub.5    CH.sub.3          H   Cl   OC.sub.2 H.sub.5                           H  white solid                                     196-198                                          43.6                                              4.15                                                  20.4                                                      7.77                                     (d)  43.6                                              4.26                                                  20.2                                                      7.92102 CH.sub.3    H     I   Cl   OC.sub.2 H.sub.5                           H  tan solid                                     184-185                                          30.6                                              2.37                                                  16.5                                                      6.28                                     (d)  30.7                                              2.39                                                  16.0                                                      5.46103 CH.sub.3    H     Cl  Cl   OC.sub.2 H.sub.5                           H  yellow solid                                     172-173                                          37.2                                              2.89                                                  20.1                                                      7.65                                     (d)  37.4                                              3.06                                                  19.7                                                      7.01104 C.sub.2 H.sub.5    CH.sub.3          H   Cl   OC.sub.3 H.sub.7 (n)                           H  yellow solid                                     165-167                                          45.0                                              4.49                                                  19.7                                                      7.51                                     (d)  44.9                                              4.51                                                  19.3                                                      7.21105 CH.sub.3    CH.sub.3          H   Cl   CO.sub.2 CH.sub.3                           H  white solid                                     206-208                                          40.7                                              3.17                                                  20.4                                                      7.77                                     (d)  40.6                                              3.05                                                  20.2                                                      7.69106 CH.sub.3    C.sub.3 H.sub.7 (i)          H   F    CH.sub.3                           H  orange solid                                     160-162                                          47.4                                              4.50                                                  22.1                                                      8.43                                          47.9                                              4.26                                                  20.1                                                      7.56107 C.sub.3 H.sub.7 (i)    CH.sub.3          H   Cl   OCH.sub.3                           H  colorless                                     202-203                                          43.6                                              4.15                                                  20.4                                                      7.77                              solid  (d)  43.4                                              4.18                                                  20.1                                                      7.58108 C.sub.3 H.sub.7 (i)    CH.sub.3          H   F    CH.sub.3                           H  tan solid                                     198-199                                          47.4                                              4.50                                                  22.1                                                      8.43                                     (d)  47.4                                              4.39                                                  21.4                                                      7.67109 C.sub.3 H.sub.7 (i)    CH.sub.3          H   Cl   OC.sub.2 H.sub.5                           H  yellow solid                                     168-170                                          45.0                                              4.29                                                  19.7                                                      7.51                                          45.2                                              4.79                                                  19.4                                                      7.40110 CH.sub.3    CH.sub.3          H   H    CO.sub.2 CH.sub.3                           H  white solid                                     218-222                                          43.8                                              4.14                                                  19.1                                                      7.37                              (acetic acid                                     (d)  44.0                                              4.20                                                  20.0                                                      7.05                              adduct)111 CH.sub.3    Cl    H   Cl   OC.sub.2 H.sub.5                           H  white solid                                     198-199                                          37.2                                              2.89                                                  20.1                                                      7.65                                     (d)  37.0                                              2.85                                                  --  7.32112 C.sub.2 H.sub.5    Cl    H   Cl   OC.sub.2 H.sub.5                           H  tan solid                                     177-179                                          38.8                                              3.26                                                  19.4                                                      7.40                                     (d)  38.9                                              3.48                                                  19.1                                                      7.64113 CH.sub.3    CF.sub.3          H   Cl   OCH.sub.3                           H  lt. tan solid                                     181-183                                          35.6                                              2.30                                                  19.2                                                      7.31                                     (d)  35.8                                              2.53                                                  18.8                                                      6.82114 CH.sub.3    CF.sub.3          H   F    CH.sub.3                           H  lt. tan solid                                     165-166                                          38.2                                              2.47                                                  20.6                                                      7.85                                     (d)  38.1                                              2.51                                                  20.2                                                      7.62115 C.sub.3 H.sub.7 (n)    CH.sub.3          H   Cl   OC.sub.2 H.sub.5                           H  lt. yellow                                     187-188                                          45.0                                              4.49                                                  19.7                                                      7.51                              solid       45.0                                              4.68                                                  19.7                                                      7.38116 C.sub.3 H.sub.7 (n)    CH.sub.3          H   Cl   OC.sub.3 H.sub.7 (n)                           H  white solid                                     181-182                                          46.3                                              4.80                                                  19.1                                                      7.27                                          46.4                                              5.04                                                  19.0                                                      7.06117 C.sub.3 H.sub.7 (n)    CH.sub.3          H   Cl   OCH.sub.3                           H  white  209-210                                          43.6                                              4.15                                                  20.4                                                      7.77                              solid  (d)  43.5                                              4.25                                                  20.2                                                      7.45118 C.sub.2 H.sub.5    CH.sub.3          H   Cl   CO.sub.2 CH.sub.3                           H  white solid                                     209-210                                          42.2                                              3.54                                                  19.7                                                      7.51                                          42.1                                              3.77                                                  19.5                                                      7.24119 CH.sub.3    CH.sub.3          H   Br   OCH.sub.3                           H  white solid                                     169-170                                          36.4                                              3.05                                                  19.6                                                      7.47                                          36.0                                              3.34                                                  18.5                                                      6.49120 C.sub.2 H.sub.5    CH.sub.3          H   Br   OCH.sub.3                           H  tan solid                                     191-192                                          37.9                                              3.41                                                  19.0                                                      7.23                                     (d)  38.0                                              3.40                                                  18.4                                                      7.00121 CH.sub.3    CH.sub.3          H   Cl   OCH.sub.2 CF.sub.3                           H  white solid                                     199-200                                          37.1                                              2.67                                                  18.6                                                      7.08                                     (d)  37.3                                              2.80                                                  18.5                                                      6.93122 C.sub.2 H.sub.5    CH.sub.3          H   Cl   OCH.sub.2 CF.sub.3                           H  white solid                                     200-201                                          38.6                                              3.02                                                  18.0                                                      6.87                                     (d)  38.8                                              3.07                                                  18.0                                                      6.64123 C.sub.2 H.sub.5    CH.sub.3          H   F    OCH.sub.3                           H  white solid                                     201-202                                          44.0                                              3.95                                                  22.0                                                      8.38                                     (d)  43.9                                              3.88                                                  21.7                                                      8.03124 CH.sub.3    CH.sub.3          H   F    OCH.sub.3                           H  white solid                                     197-198                                          40.1                                              3.91                                                  21.8                                                      8.30                                     (d)  40.3                                              4.02                                                  21.7                                                      8.04125 CH.sub.3    F     CH.sub.3              F    CH.sub.3                           H  lt. brown                                     171-172                                          42.2                                              3.27                                                  22.7                                                      8.66                              solid  (d)  42.0                                              3.57                                                  21.5                                                      8.07126 CH.sub.3    F     CH.sub.3              Cl   OCH.sub.3                           H  tan solid                                     219-221                                          38.8                                              3.00                                                  20.9                                                      7.96                                          39.0                                              2.69                                                  20.9                                                      7.77127 CH.sub.3    CH.sub.3          H   F    OC.sub.2 H.sub.5                           H  white solid                                     194-195                                          44.0                                              3.95                                                  22.0                                                      8.38                                     (d)  43.7                                              3.99                                                  22.0                                                      8.03128 C.sub.2 H.sub.5    CH.sub.3          H   F    OC.sub.2 H.sub.5                           H  white solid                                     203-204                                          45.5                                              4.32                                                  21.2                                                      8.09                                          45.2                                              4.03                                                  21.0                                                      7.76129 CH.sub.3    CH.sub.3          H   Br   OC.sub.2 H.sub.5                           H  tan solid                                     182-184                                          37.9                                              3.41                                                  19.0                                                      7.23                                          38.0                                              3.60                                                  18.9                                                      7.09130 CH.sub.3    CH.sub.3          H   Br   OC.sub.3 H.sub.7 (n)                           H  white solid                                     153-155                                          39.4                                              3.75                                                  18.4                                                      7.01                                          39.3                                              3.94                                                  18.3                                                      6.61131 C.sub.2 H.sub.5    CH.sub.3          H   Br   OC.sub.2 H.sub.5                           H  pink solid                                     194-195.5                                          39.4                                              3.75                                                  18.4                                                      7.01                                          39.0                                              3.88                                                  18.3                                                      6.79132 C.sub.2 H.sub.5    CH.sub.3          H   Br   OC.sub.3 H.sub.7 (n)                           H  white solid                                     181-183                                          40.8                                              4.06                                                  17.8                                                      6.80                                          40.8                                              4.24                                                  17.9                                                      6.54133 CH.sub.3    CH.sub.3          H   Br   OC.sub.3 H.sub.7 (i)                           H  white solid                                     182-184                                          39.4                                              3.75                                                  18.4                                                      7.01                                          38.8                                              3.83                                                  18.1                                                      6.62134 C.sub.2 H.sub.5    CH.sub.3          H   Br   OC.sub.3 H.sub.7 (i)                           H  white solid                                     197-198                                          40.8                                              4.06                                                  17.8                                                      6.80                                          40.4                                              4.21                                                  17.7                                                      6.39135 CH.sub.3    CH.sub.3          H   Cl   OC.sub.4 H.sub.9 (n)                           H  white solid                                     109-111                                          45.1                                              4.49                                                  19.7                                                      7.51                                          45.2                                              4.57                                                  19.8                                                      7.08136 CH.sub.3    CH.sub.3          H   Cl   OC.sub.4 H.sub.9 (i)                           H  white solid                                     160-192                                          45.1                                              4.49                                                  19.7                                                      7.51                                          45.2                                              4.68                                                  19.9                                                      7.34137 CH.sub.3    CH.sub.3          H   OCH.sub.3                   Cl      H  white solid                                     218-222                                          40.6                                              3.41                                                  21.8                                                      8.33                                     (d)  40.4                                              3.37                                                  21.9                                                      --138 C.sub.2 H.sub.5    CH.sub.3          H   Cl   OC.sub.4 H.sub.9 (i)                           H  yellow solid                                     139-141                                          46.3                                              4.80                                                  19.1                                                      7.27                                          45.1                                              4.99                                                  18.3                                                      6.78139 C.sub.2 H.sub.5    CH.sub.3          H   Cl   OC.sub.4 H.sub.9 (s)                           H  white solid                                     188-189                                          46.3                                              4.80                                                  19.1                                                      7.27                                          46.3                                              4.93                                                  19.3                                                      7.16140 C.sub.2 H.sub.5    CH.sub.3          H   Cl   OC.sub.4 H.sub.9 (n)                           H  white solid                                      98-100                                          46.3                                              4.80                                                  19.1                                                      7.27                                          46.4                                              5.05                                                  18.9                                                      6.77141 C.sub.2 H.sub.5    CH.sub.3          H   OCH.sub.3                   Cl      H  white solid                                     233-234                                          42.2                                              3.79                                                  21.1                                                      8.04                                          41.7                                              3.70                                                  20.8                                                      7.99142 CH.sub.3    CH.sub.3          H   Cl   OC.sub.2 H.sub.4 F                           H  off-white                                     189-109                                          40.3                                              3.39                                                  20.2                                                      7.69                              solid  (d)  40.0                                              3.40                                                  19.5                                                      7.92143 C.sub.2 H.sub.5    CH.sub.3          H   Cl   OC.sub.2 H.sub.4 F                           H  off-white                                     209-210                                          41.8                                              3.74                                                  19.5                                                      7.44                              solid       41.6                                              3.66                                                  19.0                                                      6.11144 CH.sub.3    CH.sub.3          H   Cl   OC.sub.4 H.sub.9 (s)                           H  tan solid                                     162.5-164                                          45.0                                              4.49                                                  19.7                                                      7.51                                          45.2                                              4.53                                                  19.4                                                      7.65145 CH.sub.3    CH.sub.3          H   F    I       H  white  207-208                                          31.1                                              2.17                                                  18.1                                                      6.91                              solid  (d)  31.2                                              2.09                                                  18.3                                                      6.61146 C.sub.2 H.sub.5    CH.sub.3          H   F    I       H  white  208-209                                          32.7                                              2.53                                                  17.6                                                      6.70                              solid  (d)  33.0                                              2.40                                                  17.6                                                      6.41147 CH.sub.3    CH.sub.3          H   OCH.sub.3                   CO.sub.2 CH.sub.3                           H  white  206-207                                          44.1                                              3.95                                                  20.6                                                      7.85                              solid  (d)  43.8                                              3.61                                                  20.6                                                      7.43148 C.sub.2 H.sub.5    CH.sub.3          H   OCH.sub.3                   CO.sub.2 CH.sub.3                           H  white  208-209                                          45.5                                              4.30                                                  19.9                                                      7.59                              solid  (d)  45.2                                              4.91                                                  19.7                                                      7.20149 CH.sub.3    CH.sub.3          H   F    OC.sub.3 H.sub.7 (i)                           H  white  198-199                                          45.5                                              4.32                                                  21.2                                                      8.09                              solid  (d)  45.2                                              5.07                                                  21.5                                                      7.84150 C.sub.2 H.sub.5    CH.sub.3          H   F    OC.sub.3 H.sub.7 (i)                           H  off-white                                     214-215                                          46.8                                              4.67                                                  20.5                                                      7.81                              solid  (d)  46.5                                              4.94                                                  20.5                                                      7.37151 CH.sub.3    CH.sub.3          H   F    OC.sub.3 H.sub.7 (n)                           H  yellow 176-177                                          45.5                                              4.32                                                  21.7                                                      8.09                              solid       45.1                                              4.56                                                  21.1                                                      7.70152 C.sub.2 H.sub.5    CH.sub.3          H   F    OC.sub.3 H.sub.7 (n)                           H  white  195-196                                          46.8                                              4.67                                                  20.5                                                      4.81                              solid       46.4                                              4.57                                                  20.5                                                      4.47153 CH.sub.3    CH.sub.3          H   F    CO.sub.2 CH.sub.3                           H  tan    170-171                                          42.4                                              3.31                                                  21.2                                                      8.09                              solid  (d)  42.3                                              3.56                                                  20.9                                                      7.48154 C.sub.2 H.sub.5    CH.sub.3          H   F    CO.sub.2 CH.sub.3                           H  white  162-164                                          43.9                                              3.68                                                  20.5                                                      7.81                              solid  (d)  43.9                                              4.23                                                  19.7                                                      7.16155 CH.sub.3    CH.sub.3          H   OCH.sub.3                   CF.sub.3                           H  white  204-205                                          40.2                                              3.13                                                  20.1                                                      7.66                              solid       40.2                                              3.01                                                  20.4                                                      7.54156 C.sub.2 H.sub.5    CH.sub.3          H   OCH.sub.3                   CF.sub.3                           H  tan    209-211                                          41.7                                              3.50                                                  19.4                                                      7.41                              solid       41.7                                              3.40                                                  19.5                                                      7.19157 C.sub.2 H.sub.5    CH.sub.3          H   Cl   OC.sub.2 H.sub.4 --                           H  white  138-140                                          43.4                                              4.32                                                  19.0                                                      7.24                   OCH.sub.3  solid  (d)  43.4                                              4.52                                                  19.1                                                      6.78158 CH.sub.3    CH.sub.3          H   Cl   OC.sub.2 H.sub.4 --                           H  white  166-168                                          42.0                                              4.00                                                  19.6                                                      7.48                   OCH.sub.3  solid  (d)  40.9                                              4.30                                                  18.9                                                      6.74159 CH.sub.3    CH.sub.3          H   Cl   OC.sub.2 H.sub.4 Cl                           H  white  187-188                                          38.8                                              3.26                                                  19.4                                                      7.40                              solid  (d)  39.1                                              3.57                                                  19.5                                                      6.84160 C.sub.2 H.sub.5    CH.sub.3          H   Cl   OC.sub.2 H.sub.4 Cl                           H  white  196.5-198                                          40.3                                              3.61                                                  18.4                                                      7.17                              solid       39.9                                              2.50                                                  18.7                                                      7.65161 C.sub.2 H.sub.5    CH.sub.3          H   Cl   OCH.sub.2 CHF.sub.2                           H  white  195-196                                          40.1                                              3.37                                                  18.7                                                      7.14                              solid  (d)  40.0                                              3.53                                                  18.7                                                      6.78162 CH.sub.3    CH.sub.3          H   Cl   OCH.sub.2 CHF.sub.2                           H  white  174-175                                          38.7                                              3.01                                                  19.3                                                      7.38                              solid  (d)  38.2                                              3.28                                                  19.1                                                      7.02163 CH.sub.3    CH.sub.3          H   Cl   OCH.sub.3 (CH.sub.3)--                           H  white  198.5-200                                          38.6                                              3.02                                                  18.0                                                      6.87                   CF.sub.3   solid       38.5                                              3.38                                                  17.8                                                      6.39164 C.sub.2 H.sub.5    CH.sub.3          H   Cl   OCH(CH.sub.3)--                           H  white solid                                     224-225.5                                          40.0                                              3.35                                                  17.5                                                      6.67                   CF.sub.3               40.0                                              3.62                                                  17.3                                                      6.39165 C.sub.2 H.sub.5    CH.sub.3          H   OCH.sub.3                   F       H  white solid                                     221-222                                          44.1                                              3.70                                                  22.0                                          43.7                                              3.72                                                  21.4166 CH.sub.3    CH.sub.3          H   OCH.sub.3                   CO.sub.2 C.sub.2 H.sub.5                           H  white solid                                     198-199                                          45.5                                              4.30                                                  19.9                                                      7.59                                     (d)  45.2                                              4.20                                                  20.1                                                      7.31167 C.sub.2 H.sub.5    CH.sub.3          H   OCH.sub.3                   CO.sub.2 C.sub.2 H.sub.5                           H  white solid                                     200-201                                          46.8                                              4.62                                                  19.3                                                      7.35                                          46.6                                              4.51                                                  19.4                                                      7.10168 CH.sub.3    CH.sub.3          H   OC.sub.2 H.sub.5                   CO.sub.2 CH.sub.3                           H  lt. gray                                     178-179                                          45.5                                              4.30                                                  19.9                                                      7.59                              solid  (d)  45.8                                              4.49                                                  20.1                                                      7.34169 C.sub.2 H.sub.5    CH.sub.3          H   OC.sub.2 H.sub.5                   CO.sub.2 CH.sub.3                           H  white solid                                     192-194                                          46.8                                              4.62                                                  19.3                                                      7.35                                     (d)  46.8                                              4.57                                                  19.5                                                      7.17170 CH.sub.3    CH.sub.3          H   OCH.sub.3                   F       H  white solid                                     215-216                                          42.4                                              3.56                                                  22.8                                                      8.70                                     (d)  42.1                                              3.54                                                  22.5                                                      8.54171 CH.sub.3    CH.sub.3          H   OC.sub.2 H.sub.5                   Cl      H  off-white                                     180-182                                          42.2                                              3.79                                                  21.1                                                      8.04                              solid  (d)  42.2                                              3.72                                                  20.9                                                      7.77172 C.sub.2 H.sub.5    CH.sub.3          H   OC.sub.2 H.sub.5                   Cl      H  off-white                                     199-201                                          43.6                                              4.15                                                  20.4                                                      7.77                              solid  (d)  43.5                                              4.17                                                  20.3                                                      7.75173 CH.sub.3    CH.sub.3          H   OCH.sub.3                   SCH.sub.3                           H  light yellow                                     219-220                                          42.4                                              4.07                                                  21.2                              solid  (d)  41.4                                              4.19                                                  20.0174 C.sub.2 H.sub.5    CH.sub.3          H   OCH.sub.3                   SCH.sub.3                           H  white solid                                     241-242                                          43.9                                              4.42                                                  20.5                                     (d)  43.4                                              4.13                                                  19.5175 CH.sub.3    CH.sub.3          H   F    SCH.sub.3                           H  light yellow                                     206-207                                          40.6                                              3.41                                                  21.9                                                      16.7                              solid  (d)  40.6                                              3.46                                                  20.8                                                      16.4176 C.sub.2 H.sub.5    CH.sub.3          H   F    SCH.sub.3                           H  white solid                                     218-219                                          42.2                                              3.79                                                  21.1                                                      16.1                                     (d)  41.9                                              3.59                                                  20.9                                                      16.1177 CH.sub.3    CH.sub.3          H   CH.sub.3                   CO.sub.2 CH.sub.3                           H178 C.sub.2 H.sub.5    CH.sub.3          H   CH.sub.3                   CO.sub.2 CH.sub.3                           H__________________________________________________________________________ 
    
     The compounds of Formula I wherein V represents hydrogen can generally be prepared by combining a 2-chlorosulfonyl[1,2,4]triazolo[1,5-c]pyridine compound of Formula II: ##STR4## with an appropriately substituted aminopyridine compound of Formula III: ##STR5## in the presence of pyridine or a methylpyridine compound, and, optionally but preferably, a catalytic amount of dimethyl sulfoxide. The substituents OR, Y, and Z of Formula II and A, B, and D of Formulas III are as defined hereinbefore. 
     The preparation is usually accomplished by combining the 2-chlorosulfonyl[1,2,4]triazolo[1,5-c]pyrimidine compound Formula II, the aminopyridine of Formula III, and an inert solvent, such as acetonitrile, N,N-dimethylformamide, N-methyl-2-pyrrolidinone, tetrahydrofuran, and the like, in a vessel and then adding the pyridine or methylpyridine, preferably pyridine, and a catalytic amount of dimethyl sulfoxide. The mixture is allowed to react, typically at ambient temperature, but with heating, if necessary. After a substantial quantity of the compound of Formula I has formed or a substantial quantity of the chlorosulfonyl compound of Formula II has been consumed, the desired product is recovered, typically removing the solvent by evaporation, adding water, and removing the liquids from the solid that forms by filtration or centrifugation. The product recovered can be purified, if desired, by extracting with an immiscible organic solvent, such as methylene chloride, and with water. Alternatively, the desired compounds of Formula I can be purified by recrystallization and by other commonly used methods. 
     Approximately equimolar quantities of the compounds of Formulas II and III are generally used in the preparation of compounds of Formula I although a substantial excess of one or the other may be employed. The pyridine or methylpyridine compound is generally employed in an amount of from at least 1 to about 5 moles per mole of compound of Formula II. Dimethyl sulfoxide is typically used in less than an equimolar amount; amounts over about 0.3 mole per mole of compound of Formula II are usually deleterious. Acetonitrile is often the preferred solvent. 
     It is sometimes advantageous to prepare the compounds of Formula I by condensing a chlorosulfonyl compound of Formula II with an N-trialkylsilyl derivative of a substituted aminopyridine compound. The method employed is analogous to that described in U.S. Pat. No. 4,910,306 for N-trialkylsilylanilines. The reaction conditions required are essentially the same as those described hereinabove for the condensation of a compound of Formula II with a substituted aminopyridine with the exception that the pyridine compound base may be omitted. The substituted N-trialkylsilylaminopyridine compounds employed can be prepared from the corresponding substituted aminopyridine compounds by treatment with a trialkylsilyl halide and a trialkylamine as described in U.S. Pat. No. 4,910,306 for aniline compounds. Sodium iodide is typically employed as a catalyst when the halide is chloride. The N-trialkylsilylaminopyridine compounds are typically prepared and used immediately and without purification. 
     Compounds of Formula I wherein V represents hydrogen and OR represents (C 1  -C 3 )alkoxy optionally monosubstituted with chloro or methoxy or 2,2,2-trifluoroethoxy can be made from the corresponding compounds related to those of Formula I wherein the moiety OR in the 5-position is replaced by chloro by treatment with an appropriate alkoxide reagent, such as sodium methoxide in methanol. The reaction conditions employed are similar to those used for the related exchange reactions of 2- and 4-chloropyrimidines. Non-aqueous media are preferred. Selective replacement of chlorine in the 5-position can readily be achieved as this chlorine is much more reactive than chlorine in the 7-and 8-positions (Y and/or Z represent Cl). 
     Compounds of Formula I wherein V represents COR&#39;, CO 2  R&#34;, or CONR&#34;&#39; 2  can be prepared from compounds of Formula I wherein V represents hydrogen by acylation with a compound of the formula C 1  COR&#39;, C 1  CO 2  R&#34;, or C 1  CONR&#34;&#39; 2 , respectively, using conventional procedures known in the art for the acylation of sulfonamides. 
     The 2-chlorosulfonyl[1,2,4]triazolo[1,5-c]pyrimidine compounds of Formula II and their analogs wherein the moiety OR is replaced by chloro can be prepared by the methods taught in U.S. Pat. No. 5,010,195. 
     The preparation of several substituted 3-aminopyridines, notably those wherein A represents chloro or fluoro, and B represents alkyl, alkoxy or alkylthio is described in the Examples. Other substituted 3-aminopyridines of interest as intermediates for the compounds of Formula I are known in the art or can be prepared by the general methods known in the art or provided herein. 
     4-Alkoxy-3-amino-2-chloropyridine compounds can be prepared by chlorination of known 4-alkoxy-3-aminopyridine compounds. 4-Alkoxy-3-amino-2-fluoropyridine compounds can be prepared from 4-alkoxy-2-fluoropyridine compounds by lithiation with butyl lithium and treatment of the intermediate with diphenyl phosphoryl azide. 4-Alkoxy-2-fluoropyridine compounds can be prepared by reduction of 4-Alkoxy-3,5-dichloro-2-fluoropyridine. compounds with hydrogen. Many 4-substituted 2-alkoxy-3-aminopyridine compounds can be prepared from 2-alkoxy-3-aminopyridine compounds by lithiation of the corresponding t-butoxycarbonyl derivative and reaction of this with an electrophilic reagent in processes closely related to those disclosed in J. Organic Chemistry, 60, 1875-1877 (1995). Thus, 2-alkoxy-3-amino-4-fluoropyridine compounds can be prepared from [-butyl N-(2-alkoxy-3-pyridinyl)carbamates by fluorination with N-fluorodibenzenesulfonimide of the intermediate obtained on lithiation with t-butyl lithium followed by treatment with anhydrous p-toluenesulfonic acid to remove the protecting t-butoxycarbonyl group. Similarly, 2-alkoxy-3-amino-4-chloropyridine compounds can be obtained by chlorination of t-butyl N-(2-alkoxy-3-pyridinyl)carbamates with hexachloroethane in an analogous process. Alkyl 3-amino-2-alkoxyisonicotinate compounds can be prepared analogously from t-butyl N-(2-alkoxy-3-pyridinyl)carbamate compounds by lithiating with butyl lithium, treating the intermediate formed with carbon dioxide and then an alkyl iodide, and finally removing the protecting t-butoxycarbonyl group by treatment with anhydrous p-toluenesulfonic acid. The amine-protected t-butyl N-(2-alkoxy-3-pyridinyl)carbamate compounds can be prepared from 2-alkoxy-3-aminopyridine compounds by treatment with di-t-butyl dicarbonate. 3-Amino-2-chloroisonicotinic acid esters can be prepared by chlorination of 3-aminoisonicotinic acid esters using 1,3-dichloro-5,5-dimethylhydantion as the chlorinating agent. 3-Amino-2-fluoro-4-methylpyridine can be prepared by palladium on carbon catalyzed reduction of 2-fluoro-4-methyl-3-nitropyridine with hydrogen. This compound can be converted to other 4-alkyl-3-amino-2-fluoropyridine compounds by alkylation of the methyl group. These and other 3-aminopyridine compounds of Formula III can be made using a variety of preparative methods well-established in the art. 
     while it is possible to utilize the [1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide compounds of Formula I directly as herbicides, it is preferable to use them in mixtures containing an herbicidally effective amount of the compound along with at least one agriculturally acceptable adjuvant or carrier. Suitable adjuvants or carriers should not be phytotoxic to valuable crops, particularly at the concentrations employed in applying the compositions for selective weed control in the presence of crops, and should not react chemically with the compounds of Formula I or other composition ingredients. Such mixtures can be designed for application directly to weeds or their locus or can be concentrates or formulations which are normally diluted with additional carriers and adjuvants before application. They can be solids, such as, for example, dusts, granules, water dispersible granules, or wettable powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions. 
     Suitable agricultural adjuvants and carriers that are useful in preparing the herbicidal mixtures of the invention are well known to those skilled in the art. 
     Liquid carriers that can be employed include water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methanol, ethanol, isopropanol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, and the like. Water is generally the carrier of choice for the dilution of concentrates. 
     Suitable solid carriers include talc, pyrophyllite clay, silica, attapulgus clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonire clay, Fuller&#39;s earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, and the like. 
     It is frequently desirable to incorporate one or more surface-active agents into the compositions of the present invention. Such surface-active agents are advantageously employed in both solid and liquid compositions, especially those designed to be diluted with carrier before application. The surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes. Typical surface active agents include salts of alkyl sulfates, such as diethanoiammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C 18  ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C 16  ethoxylate; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosucclinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono and dialkyl phosphate esters. 
     Other adjuvants commonly utilized in agricultural compositions include antifoam agents, compatibilizing agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, penetration aids, spreading agents, sticking agents, dispersing agents, thickening agents, freeze point depressants, antimicrobial agents, and the like. The compositions can also contain other compatible components, for example, other herbicides, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like. 
     The concentration of the active ingredients in the herbicidal compositions of this invention is generally from about 0.001 to about 98 percent by weight. Concentrations from about 0.01 to about 90 percent by weight are often employed. In compositions designed to be employed as concentrates, the active ingredient is generally present in a concentration from about 5 to about 98 weight percent, preferably about 10 to about 90 weight percent. Such compositions are typically diluted with an inert carrier, such as water, before application. The diluted compositions usually applied to weeds or the locus of weeds generally contain about 0.001 to about 5 weight percent active ingredient and preferably contain about 0.01 to about 0.5 percent. 
     The present compositions can be applied to weeds or their locus by the use of conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation water, and by other conventional means known to those skilled in the art. 
     The compounds of Formula I have been found to be useful preemergence and postemergence herbicides. They can be employed at non-selective (higher) rates of application to control essentially all of the vegetation in an area or, in some cases, at selective (lower) rates of application for the selective control of undesirable vegetation in grass crops, such as corn, wheat, barley, and rice as well as in broadleaf crops, such as soybeans and cotton. While each of the N-pyridinyl[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide compounds encompassed by Formula I is within the scope of the invention, the degree of herbicidal activity, the crop selectivity, and the spectrum of weed control obtained varies depending upon the substituents present. 
     The term herbicide is used herein to mean an active ingredient which controls or adversely modifies the growth of plants. An herbicidally effective or vegetation controlling amount is an amount of active ingredient which causes an adversely modifying effect and includes deviations from natural development, killing, regulation, desiccation, retardation, and the like. The terms plants and vegetation are meant to include germinant seeds, emerging seedlings and established vegetation. 
     Herbicidal activity is exhibited by the compounds of the present invention when they are applied directly to the plant or to the locus of the plant at any stage of growth or before emergence. The effect observed depends upon the plant species to be controlled, the stage of growth of the plant, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the specific compound employed, the specific adjuvants and carriers employed, the soil type, and the like, as well as the amount of chemical applied. These and other factors can be adjusted as is known in the art to promote selective herbicidal action. Generally, it is preferred to apply the compounds of Formula I postemergence to relatively immature plants to achieve the maximum control of broadleaf weeds. 
     Application rates of about 0.001 to about 1 Kg/Ha are generally employed in postemergence operations; for preemergence applications, rates of about 0.01 to about 10 Kg/Ha are generally employed. The higher rates designated generally give non-selective control of a broad variety of undesirable vegetation. The lower rates typically give selective control and, by judicious election, can be employed in the locus of crops. 
     EXAMPLES 
     The following Examples are presented to illustrate the various aspects of this invention and should not be construed as limitations to the claims. 
     1. Preparation of 3-Amino-2-fluoro-4-methylpyridine 
     To a solution of 10.1 g (grams) (65 mmol (millimole)) of 2-fluoro-4-methyl-3-nitropyridine in 200 mL (milliliter) of ethyl acetate was added 25 g (0.40 mol) of acetic acid and 0.8 g of 5 percent palladium on carbon catalyst. This mixture was shaken under 50 psig (pounds per square inch gauge, 2400 kiloPascals) pressure of hydrogen for 18 hours, was filtered, and was concentrated by evaporation under reduced pressure to obtain an oil. This oil was partitioned between dilute aqueous sodium bicarbonate and ether. The organic phase was separated, dried over magnesium sulfate, and filtered. The filtrate was concentrated by evaporation under reduced pressure and the residue was purified by column chromatography to obtain 7.2 g (88 percent of theory) of the title compound as a colorless solid melting at 63°-64° C. 
     Elemental Analysis C 6  H 7  FN 2  Calc.: %C, 57.1; %H, 5.59; %N, 22.2 Found: %C, 57.2; %H, 5.73; %N, 22.1 
       1  H NMR (nuclear magnetic resonance spectrum (200 megahertz)) CDCl 3  :7.4 (d, 1H, J=5.0); 6.8 (d, 1H, J=5.0); 3.7 (br, 2H); 2.1 (s, 3H); 13C NMR CDCl 3  :152.6 (d, J=229); 134.1 (d, J=8.6); 133.8 (d, J=14.5); 128.1 (d, J=27.1); 123.3, 16.4 (d, J=4.1). 3-Amino-2-fluoro-5-methylpyridine was prepared analogously from 2-fluoro-5-methyl-3-nitropyridine. This compound was obtained in 89 percent yield as white solid melting at 27°-28.5° C. 
     Elemental Analysis C 6  H 7  FN 2  Calc.: %C, 57.1; %H, 5.59; %N, 22.2 Found: %C, 56.9, %H, 5.65; %N, 22.6 
       1  H NMR CDCl 3  : 7.2 (d, 1H); 6.8 (d, 1H); 3.7 (br, 2H); 2.1 (s, 3H);  13  C NMR CDCl 3  : 151.8 (d, J=229); 134.5 (d, J=12.6); 132.2 (d, J=3.9); 129.9 (d, J=28.7); 125.8 (d, J=5.3), 17.8. 
     2. Preparation of 3-Amino-2-chloro-4-methoxypyridine 
     To a solution of 6.4 g (51 mmol) of 3-amino-4-methoxypyridine in 30 mL of 37 percent aqueous hydrochloric acid was slowly added 7.8 g of 30 percent aqueous hydrogen peroxide at room temperature with stirring. After 30 min this solution was slowly poured into 300 mL of saturated aqueous sodium bicarbonate and the resulting mixture was extracted with ether (3×200mL). The ethereal extracts were combined, dried over magnesium sulfate, and filtered, The fittrate was concentrated by evaporation under reduced pressure to obtain a light brown solid. This solid was purified by column chromatography (17:83 acetone:hexane) to obtain 6.54 g (81 percent of theory) of the title compound as colorless needles melting at 86°-87° C. 
     Elemental Analysis C 6  H 7  ClN 2  O Calc.: %C, 45.4; %H, 4.45; %N, 17.7 Found: %C, 45.4; %H, 4.65; %N, 17.8 
       1  H NMR CDCl 3  : 7.7 (d, 1H, J=5.4), 6.6 (d, 1H, J=5.4 , 4.0 (br, 2H), 3.8 (s, 3H);  13  C NMR CDCl 3  : 153.3, 138.5, 135.6, 129.9, 105.2, 55.9. 
     3-Amino-2-chloro-4-ethoxypyridine was prepared from 3-amino-4-ethoxypyridine in an analogous procedure and was obtained as a white solid melting at 72°-73° C. 
     Elemental Analysis C 7  H 9  ClN 2  O Calc.: %C, 48.7; %H, 5.26; %N, 16.2 Found: %C, 48.9; %H, 4.98; %N, 16.5. 
       1  H NMR CDCl 3  : 7.7 (d, 1H, J=5.4), 6.6 (d, 1H, J=5.4), 4.1 (q, 2H, J=7.0), 4.0 (br, 2H), 1.5 (t, 3H, J=7.0). 
     3-Amino-2-chloro-4-propoxypyridine was prepared from 3-amino-4-propoxypyridine in an analogous procedure and was obtained as a white solid melting at 46°-47° C. 
     Elemental Analysis C 8  H 11  ClN 2  O Calc.: %C, 51.5; %H, 5.94; %N, 15.0 Found: %C, 51.8; %H, 5.97; %N, 15.2 
       1  H NMR CDCl 3  : 7.7 (d, 1H, J=5.4), 6.6 (d, 1H, J=5.4), 4.1 (br, 2H), 4.0 (t, 2H, J=6.5), 1.84 (m, 2H), 1.0 (t, 3H, J=7.4 ). 
     3-Amino-2-chloro-4-(1-methylethoxy)pyridine was prepared from 3-amino-4-(1-methylethoxy)pyridine in an analogous procedure and was obtained as an amber oil. 
     Elemental Analysis C 8  H 11  ClN 2  O Calc.: %C, 51.5; %H, 5.94; %N, 15.0 Found: %C, 51.1; %H, 5.87; %N, 15.4 
       1  H NMR CDCl 3  : 7.7 (d,  1  H, J=5.5), 6.6 (d,  1  H, J=5.4), 4.6 (m,  1  H, J=6.0), 4.0 (br, 2H), 1.34 (d, 6H, J=6.0). 
     3. Preparation of 3-Amino-2-ethylthio-4-methylpyridine 
     2-Ethylthio-4-methyl-3-nitropyridine (10.0 g, 50.4 mmol) was added slowly with stirring to a solution of 57 g (0.25 mole) of stannous chloride in 250 mL of concentrated aqueous hydrochloric acid. An exothermic reaction took place. The solution was held at 70° C. for 30 min, cooled, and then poured slowly into saturated aqueous sodium bicarbonate solution. The resulting mixture was extracted with ether and the extract was dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain 5.8 g (68 percent of theory) of a light yellow oil that solidified upon standing. This solid was recrystallized from hexane to obtain 3.2 g of the title compound as a white solid melting at 37°-38° C. 
     Elemental Analysis C 8  H 12  N 2  S Calc.: %C, 57.1; %H, 7.19; %N, 16.7; %S, 19.1 Found: %C, 57.3; %H, 6.88; %N, 16.8; %S, 19.0 
       1  H NMR CDCl 3  : 7.8 (d, 1H, J=4.8), 6.7 (d, 1H, J=4.8), 3.8 (br, 2H), 3.2 (q, 2H, J=7.4), 2.1 (s, 3H), 1.3 (t, 3H, J=7.4).  13  C NMR CDCl 3  : 142.2, 139.5, 139.3,128.9, 122.4, 25.4, 17.0, 15.0. 
     4. Preparation of Methyl 3-Amino-2-chloroisonicotinate 
     A mixture of 18 g (118 mmol) of methyl 3-aminoisonicotinate and 12 g (60 mmol) of 1,3-dichloro-5,5-dimethylhydantoin in 1500 mL of tetrachloroethylene was warmed slowly to 80° C. with stirring and held there for 3 hours. The solution was then cooled, filtered, washed with dilute aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain a dark oil. This oil was purified by careful column chromatography to give 6.7 g (30 percent of theory) of the title compound as a colorless solid melting at 91°-92° C. 
     Elemental Analysis C 7  H 7  ClN 2  O 2  Calc.: %C, 45.1; %H, 3.78; %N, 15.0 Found: %C, 45.2; %H, 3.94; %N, 15.1 
       1  H NMR CDCl 3  : 7.7 (d, 1H, J=5.1); 7.6 (d, 1H, J=5.1; 6.2 (br, 2H); 3.9 (s, 3H);  13  C NMR CDCl 3  : 166.7, 141.9, 139.0, 134.7, 122.8, 116.5, 52.3. 
     5. Preparation of 3-Amino-4-ethyl-2-fluoropyridine 
     Trimethylsilyl chloride (2.2 g, (0.18 mmol) and sodium iodide (2.7 g, 0.18 mmol) were added to a solution of 3.6 g (0.15 mmol) of t-butyl N-(4-ethyl-2-fluoro-3-pyridyl)carbamate in 50 mL of dry acetonitrile with stirring at ambient temperature. After 2 hours the mixture was poured into ether and the resulting solution was washed with dilute aqueous sodium bisulfite, dried over magnesium sulfate, and filtered. The liltrate was concentrated by evaporation under reduced pressure to obtain an oil. This oil was purified by column chromatography to obtain 1.6 g (76 percent of theory) of the title compound as a gold oil. 
     Elemental Analysis C 7  H 9  FN 2  Calc.: %C, 60.0; %H, 6.47; %N, 20.0 Found: %C, 59.8; %H, 6.66; %N, 20.2 
       1  H NMR CDCl 3  : 7.4 (d, 1H, J=5.0); 6.8 (d, 1H, J=5.0); 3.7 (br, 2H); 2.45 (q, 2H, J=7.5); 1.2 (t, 3H, J=7.5). 
     3-Amino-4-(1-methylethyl)-2-fluoropyridine was prepared in an analogous way from t-butyl N-(4-(1-methylethyl)-2-fluoro-3-pyridyl)carbamate. This compound was obtained in 92 percent yield as a gold oil. 
     Elemental Analysis C 8  H 11  FN 2  Calc.: %C, 62.3; %H, 7.19; %N, 12.3 Found: %C, 62.5; %H, 7.24; %N, 12.6. 
       1  H NMR CDCl 3  :7.4 (d, 1H, J=5.2); 6.8 (d, 1H, J=5.1; 3.8 (br, 2H); 2.87 (m, 1H); 1.2 (d, 6H, J=6.8). 
     6. Preparation of t-Butyl N-(4-Ethyl-2-fluoro-3-pyridyl)carbamate 
     A solution of lithium diisopropylamine (LDA) was prepared from 19.3 mL (137 mmol) of diisopropylamine and 55 mL (137 mmol) of 2.5 H n-butyllithium in hexane in 250 mL of dry tetrahydrofuran at -20° C. A solution of 14.4 g (62.5 mmol) of t-butyl N-(4-methyl-2-fluoro-3-pyridyl)carbamate in 80 mL of dry tetrahydrofuran was added dropwise with stirring at a rate slow enough to maintain the temperature below -60° C. After a 30 min reaction period, 27 g (190 mmol) of methyl iodide was added and the solution was allowed to warm to -10° C. The resulting mixture was diluted with 100 mL of aqueous ammonium chloride and 200 mL of ether and the phases were separated. The aqueous phase was washed with ether (3×100 mL). The organic phase and ether washes were combined, dried over magnesium sulfate, and filtered. The filtrate was concentrated by evaporation under reduced pressure to obtain a gold oil. This oil was purified by column chromatography to obtain 11.4 g (76 percent of theory) of the title compound as a white solid melting at 84°-86° C. 
       1  H NMR CDCl 3  : 7.7 (d, 1H, J=5.08); 6.8 (d, 1H, J=5.08); 6.1 (br, 1H); 2.45 (q, 2H, J=7.6); 1.2 (s, 9H); 1.0 (t, 3H, J=7.6). 
     t-Butyl N-(4-(1-methylethyl)-2-fluoro-3-pyridyl)carbamate was prepared analogously from t-butyl N-(4-ethyl-2-fluoro-3-pyridyl)carbamate. This compound was obtained in 69 percent yield as a colorless solid melting at 60°-62° C. 
     Elemental Analysis C 13  H 19  FN 2  O 2  Calc.: %C, 61.4; %H, 7.53; %N, 11.0 Found: %C, 61.6; %H, 7.78; %N, 11.3. 
       1  H NMR CDCl 3  : 7.9 (d, 1H, J=5.4); 7.0 (d, 1H, J=5.4); 6.0 (br, 1H); 3.2 (m, 1H); 1.4 (s, 9H); 1.2 (d, 6H, J=5.2). 
     7. Preparation of 3-Amino-2,4,5-trichloropyridine 
     Thirty percent aqueous hydrogen peroxide (3.0 g, 26 mmol) was added dropwise with stirring at 15° C. to a solution of 8.0 g (49mmol) of 3-amino-4,5-dichloropyridine in 450mL of 37 percent aqueous hydrochloric acid. After 30 min another 2.6 g (23 mmol) of 30 percent aqueous hydrogen peroxide was added and the solution was allowed to slowly warm to room temperature. The resulting mixture was diluted with water, neutralized with sodium carbonate, and extracted with ether. The ethereal extract was dried over magnesium sulfate and filtered. The liltrate was concentrated by evaporation under reduced pressure to obtain a viscous oil. This oil was partially purified by column chromatography to obtain 2.5 g (26 percent of theory) of the title compound, a white solid melting at 88°-90° C., and 5.3 g of a mixture of the title compound and 3-amino-2,4,5,6-tetrachloropyridine. 
     Elemental Analysis C 5  H 3  Cl 3  N 2  Calc.: %C, 30.4; %H, 1.53; %N, 14.2 Found: %C, 30.5; %H, 1.47; %N, 14.1. 
       1  H NHR CDCl 3  : 7.7 (s, 1H); 4.6 (br, 2H). 
     8. Preparation of 3-Amino-4-fluoro-2-methoxypyridine 
     A solution 5.0 g (26.2 mmol) of p-totuenesulfonic acid monohydrate in 150 mL of toluene was refluxed to azeotropically remove the water and was then allowed to cool. A 5.0 g (20.6 mmol) amount of t-butyl N-(4-fluoro-2-methoxy-3-pyridyl)carbamate was added and the solution was heated to reflux with stirring for 5 min. The mixture was cooled and the liquid was removed by decantation. The solid residue was partitioned between ether and saturated aqueous sodium carbonate and the organic phase was recovered, dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue was purified by flash chromatography to obtain 2.7 g (91 percent of theory) of the title compound as a near-clear oil. 
     Elemental Analysis C 6  H 7  FN 2  O Calc.: %C, 50.7; %H, 4.96; %N, 19.7 Found: %C, 50.9; %H, 5.26; %N, 19.1. 
       1  HNMR (CDCl 3 ): 7.5 (dd, 1H, j=5.7, 7.8); 6.6 (dd, 1H, j=5.7, 9.4); 3.9 (s, 3H); 3.7 (br, 2H). 
     9. Preparation of t-butyl N-(4-Fluoro-2-methoxy-3-pyridinyl)carbamate 
     To a solution of 8 g (35.7 mmol) of t-butyl N-(2-methoxy-3-pyridyl)carbamate in 200 mL of dry tetrahydrofuran was added with stirring at -60° C., 46.2 mL (78.5 mmol) of 1.7M t-butyl lithium in pentane. The resulting solution was allowed to warm slowly with stirring to -20° C. over a 20 to 30 min period. It was then cooled to about -60° C. and 12.2 g (38.7 mmol) of N-fluorodibenzenesulfonimide was added with stirring all at once. The mixture was allowed to warm to -20° C. and was poured into 500 mL of ether. The resulting ethereal solution was washed with a mixture of 2.5 g (41.7 mmol) of acetic acid and 150 mL of water. The aqueous phase was extracted with 200 mL of ether. The ethereal extracts were combined, dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue was purified by flash chromatography to obtain 6.7 g (77 percent of theory) of the title compound as a colorless solid melting at 75°-77° C. 
     Elemental Analysis C 11  H 15  FN 2  O 3  Calc.: %C, 54.5; %H, 6.24; %N, 11.6 Found: %C, 54.2; %H, 6.39; %N, 11.4. 
       1  H NMR (CDCl 3 ): 7.88 (dd, 1H, j=5.8, 7.6); 6.68 (dd, 1H, j=5.8, 8.9); 5.9 (br, 1H); 3.9 (s, 3H); 1.45 (s, 9H 
     10. Preparation of Methyl 3-Amino-2-ethoxyisonicotinate 
     A solution 7.5 g (39.4 mmol) of p-toluenesulfonic acid monohydrate in 150 mL of toluene was refluxed to azeotropically remove the water. The mixture was allowed to cool and then 11.0 g (37.1 mmol) of t-butyl N-(4-carboxymethyl-2-ethoxy-3-pyridyl)carbamate was added with stirring and the solution was heated to 95° C. for 15 min. The resulting mixture was cooled and the liquid was removed by decantation. The solid residue was partitioned between ether and saturated aqueous sodium carbonate. The organic phase was recovered, dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue was purified by column chromatography to obtain 6.4 g (88 percent of theory) of the title compound as a light yellow solid melting at 59°-60.5° C. 
     Elemental Analysis C 9  H 12  N 2  O 3  : Calc.: %C, 55.1; %H, 6.16; %N, 14.3 Found: %C, 54.6; %H, 6.00; %N, 14.5. 
       1  H NMR (CDCl 3 ): 7.3 (d, 1H, j=5.6); 7.1 (d, 1H, j=5.6); 5.9 (br, 2H); 4.3 (q, 2H, j=7.1); 3.8 (s, 3H); 1.37 (t, 3H, j=7.1). 
     Methyl 3-amino-2-methoxyisonicotinate, an amber oil, was prepared analogously. 
     Elemental Analysis C 8  H 10  N 2  O 3  Calc.: %C, 50.0; %H, 4.80; %N, 16.7 Found: %C, 50.2; %H, 5.26; %N, 16.6. 
     1H NMR (CDCl 3 ): 7.3 (d, 1H, j=5.6); 7.1 (d, 1H, j=5.6); 5.9 (br, 2H); 3.96 (s, 3H); 3.8 (s, 3H). 
     Ethyl 3-amino-2-methoxyisonicotinate, a light yellow oil, was prepared analogously. 
     Elemental Analysis C 9  H 12  N 2  O 3  Calc.: %C, 55.1; %H, 6.16; %N, 14.3 Found: %C, 54.2; %H, 6,56; %N, 14.6. 
       1  H NMR (CDCl 3 ): 7.3 (d, 1H, j=5.6); 7.1 (d, 1H, j=5.6); 5.9 (br, 2H); 4.28 (q, 2H, j=7.2); 3.9 (s, 3H); 1.33 (t, 3H, j=7.14). 
     11. Preparation of t-Butyl N-(4-Carboxymethyl-2-ethoxy -3-pyridinyl)carbamate 
     To a solution of 12.0 g (50.3 mmol) of t-butyl N-(2-ethoxy-3-pyridinyl)carbamate in 200 mL of dry tetrahydrofuran was added with stirring at -50° C., 66 mL (111 mmol) of 1.7M t-butyl lithium in pentane. The resulting solution was allowed to warm slowly to 0° C. over a 20 to 30 min period and was then cooled to -60° C. and poured into 500 mL of ether saturated with crushed dry ice (carbon dioxide). The resulting mixture was acidified at room temperature with 3.0 g (50 mmol) of acetic acid and the fine white solid precipitate that formed was collected by filtration and dried under reduced pressure at 50° C. to obtain 17.0 g of a lithium salt containing some tetrahydrofuran. This salt was combined with 30.0 g (211 mmol) of iodomethane in 150 mL of dry dimethyl sulfoxide and the mixture was stirred for 1 hr. It was then poured into 400 mL of water. The aqueous mixture was extracted with 500 then 200 mL of ether. The ether extracts were combined, dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue was purified by column chromatography to obtain 11.5 g (77 percent of theory) of the title compound as a colorless solid melting at 94°-95.5° C. 
     Elemental Analysis C 14  H 20  N 2  O 5  Calc.: %C, 56.8; %H, 6.80; %N, 9.45 Found: %C, 56.8; %H, 7.00; %N, 9.63. 
       1  H NMR (CDCl 3 ): 7.8 (d, 1H, j=5.3); 7.1 (d, 1H, j=5.3); 6.9 (br, 1H); 4.4 (q, 2H, j=7.0); 3.8 (s, 3H); 1.46 (s, 9H); 1.37 (t, 3H, j=7.0). t-Butyl N-(4-carboxyethyl-2-methoxy-3-pyridinyl)carbamate, a colorless solid melting at 40°-41° C., was prepared analogously. 
     Elemental Analysis C 14  H 20  N 2  O 5  Calc.: %C, 56.8; %H, 6.80; %N, 9.45 Found: %C, 56.6; %H, 6.76;% N, 9.26. 
       1  H NMR (CDCl 3 ): 7.9 (d, 1H, j=5.3); 7.1 (d, 1H, j=5.25); 6.9 (br, 1H); 4.27 (q, 2H, j=7.15); 3.96 (s, 3H); 1.45 (s, 9H); 1.33 (t, 3H, j=7.14). 
     t-Butyl N-(4-Carboxymethyl-2-methoxy-3-pyridinyl)carbamate, a colorless solid melting at 107°-108° C., was obtained analogously. 
     Elemental Analysis C 13  H 18  N 2  O 5  Calc.: %C, 55.3; %H, 6.43; %N, 9.92 Found: %C, 55.5; %H, 6.22; %N, 10.1. 
     1H NMR (CDCl 3 ): 7.9 (d, 1H, j=5.3); 7.1 (d, 1H, j=5.4); 6.9 (br, 1H); 3.97 (s, 3H); 1.46 (s, 9H). 
     12. Preparation of t-Butyl N-(4-Chloro-2-ethoxy-3-pyridinyl)carbamate 
     To a solution of 15 g (63 mmol) of t-butyl N-(2-ethoxy-3-pyridinyl)carbamate in 175 mL of dry tetrahydrofuran was added with stirring at -60° C., 78 mL (132 mmol) of 1.7M t-butyl lithium in pentane. The resulting solution was allowed to warm to -10° C. over a 30 min. period and was then cooled to -60° C. A 22.3 g (94 mmol) amount of hexachloroethane was added all at once with stirring and the mixture are allowed to warm to ambient temperature. It was then diluted with 600 mL of ether and the resulting solution was washed with 150 mL of water, dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue was purified by column chromatography to obtain 11.1 g (65 percent of theory) of the title compound as a colorless solid melting at 73°-74° C. 
     Elemental Analysis C 12  H 17  ClN 2  O 3  : Calc.: %C, 52.9; %H, 6.28; %N, 10.3 Found: %C, 53.0; %H, 6.30; %N, 10.3. 
       1  H NMR (CDCl 3 ): 7.88 (d, 1H, j=5.5); 6.93 (d, 1H, j=5.5); 6.0 (br, 1H); 4.4 (q, 2H, j=7.0); 1.5 (s, 9H); 1.39 (t, 3H, j=7.0.). 
     13. Preparation of t-Butyl N-(2-Ethoxy-3-pyridinyl)carbamate 
     To a solution of 38.1 g (0.28 mol) of 3-amino-2-ethoxypyridine in 400 mL of dry dioxane was added with stirring 60 g (0.28 mol) of di-t-butyl dicarbonate and the solution was slowly heated to reflux over a 4 hr period. The resulting solution was cooled below reflux and another 5.0 g (23 mmol) of di-t-butyl dicarbonate was added with stirring and the mixture was reheated at reflux for 1 hr. The volatiles were removed by evaporation under reduced pressure and the residue obtained was purified by column chromatography to obtain 58.3 g (89 percent of theory) of the title compound as a colorless oil. 
     Elemental Analysis C 12  H 18  N 2  O 3  Calc.: %C, 60.5; %H, 7.61; %N, 11.8 Found: %C, 59.7; %H, 9.03; %N, 11.9. 
       1  H NMR (CDCl 3  ): 8.2 (broad d, 1H, j=7.0 ); 7.7 (d, 1H, j=5.0); 6.9 (br, 1H); 6.8 (dd, 1H, j=5.0, 5.0), 4.4 (q, 2H, j=7.1); 1.47 (s, 9H); 1.36 (t, 3H, j=7.1). 
     14. Preparation of 3-Amino-4-ethoxy-2-fluoropyridine 
     To a solution of 19 g (74 mmol) of t-butyl N-(4-ethoxy-2-fluoro-3-pyridinyl)carbamate and 12.2 g (81.5 mmol) of sodium iodide in 400 mL of dry acetonitrile was added with stirring 8.9 g (81.5 mmol) of trimethylsilyl chloride. The mixture was allowed to react for 4 hr and then a 100 mL solution of aqueous sodium bicarbonate was added with stirring. The resulting mixture was extracted with 1 L of ether and the ether extract was dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue was purified by column chromatography to obtain 6.3 g (55 percent of theory) of the title compound as a colorless solid melting at 76°-77° C. 
     Elemental Analysis C 7  H 9  FN 2  O Calc.: %C, 53.5; %H, 5.81; %N, 17.9 Found: %C, 54.3; %H, 6.44; %N, 17.7. 
       1  H NMR (CDCl 3 ): 7.5 (d, 1H, j=5.74); 6.5 (d, 1H, j=5.64); 4.1 (q, 2H, j=7.0); 3.6 (br, 2H); 1.4 (t, 3H, j=6.9). 
     3-Amino-2-fluoro-4-methoxypyridine, a colorless solid melting at 48°-50° C., was prepared analogously. 
     Elemental Analysis C 6  H 7  FN 2  O Calc.: %C, 50.7; %H, 4.96; %N, 19.7 Found: %C, 50.9; %H, 5.13; %N, 19.9. 
       1  H NMR (CDCl 3 ): 7.5 (d, 1H, j=5.57 ); 6.63 (d, 1H, j=5.47); 3.8 (s, 3H); 3.7 (br, 2H). 
     3-Amino-2-fluoro-4-propoxypyridine, a colorless oil, was prepared analogously. 
     Elemental Analysis C 8  H 11  FN 2  O Calc.: %C, 55.5; %H, 6.51; %N, 16.5 Found: %C, 56.7; %H, 6.66; %N, 16.2. 
       1  H NMR (CDCl 3 ): 7.4 (d, 1H, j=5.61; 6.5 (d, 1H, j=5.71); 4.5 (t, 2H, j=6.5); 3.7 br, 2H); 1.8 (m, 2H, j=7.3); 1.0 (t, 3H, j=7.4). 
     3-Amino-2-fluoro-4-(1-methylethoxy)pyridine, a gold oil, was prepared analogously. 
     Elemental Analysis C 8  H 11  FN 2  O Calc.: %C, 55.5; %H, 6.51; %N, 16.5 Found: %C, 56.9; %H, 6.69; %N, 16.4. 
       1  H NMR (CDCl 3 ): 7.5 (d, 1H, j=5.57); 6.6 (d, 1H, j=5.71); 4.5 (m, 1H, j=6.0); 3.6 (br, 2H); 1.3 (d, 6H, j=6.1). 
     15. Preparation of t-Butyl N-(4-ethoxy-2-fluoro-3-pyridinyl)carbamate 
     To a solution of 18.5 g (131 mmol) of 4-ethoxy-2-fluoropyridine in 300 mL of dry tetrahydrofuran at -78° C. was added slowly, with stirring and cooling to maintain the temperature below -65° C., 58 mL of 2.5M butyl lithium in hexane. The mixture was allowed to react for 1 hr and then the resulting slurry was poured into 1300 mL of ether containing excess powdered dry ice (carbon dioxide). The fine white precipitate that formed was collected by filtration and dried under reduced pressure for 90 min. The hygroscopic solid obtained was taken into 700 mL of t-butanol and 68 g (0.24 mol) of diphenyl phosphoryl azide was added with stirring. This mixture was slowly warmed to reflux for 2 hr during which time there was a vigorous evolution of nitrogen. The resulting slurry was filtered and the filtrate was diluted with 800 mL of dichloromethane. The organic phase was separated, washed with water (2×100 mL), and concentrated by evaporation to obtain a semi-solid residue. This was dissolved in fresh dichloromethane and the solution was dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue was purified by column chromatography to obtain 19.5 g (63 percent of theory) of the title compound as a colorless solid melting at 130°-131° C. 
     Elemental Analysis C 12  H 17  FN 2  O 3  Calc.: %C, 56.2; %H, 6.69; %N, 10.9 Found: %C, 56.1; %H, 6.99; %N, 11.3. 
       1  H NMR (CDCl 3 ): 7.85 (d, 1H, j=5.7); 6.6 (d, 1H, j=5.7); 6.0 (br, 1H); 4.1 (q, 2H, j=7.0); 1.4 (t, 3H, j=6.9); 1.35 (t, 3H, j=7.0). 
     t-Butyl N-(2-fluoro-4-(1-methylethoxy)-3-pyridinyl)carbamate, a colorless solid melting at 80°-81.5° C., was obtained analogously. 
     Elemental Analysis C 13  H 19  FN 2  O 3  Calc.: %C, 57.8; %H, 7.09; %N, 10.4 Found: %C, 57.9; %H, 6.94; %N, 10.7. 
       1  H NMR (CDCl 3 ): 7.9 (d, 1H, j=5.9); 6.7 (d, 1H, j=5.96); 6.0 (br, 1H); 4.6 (m, 1H, j=6.1); 1.45 (s, H); 1.35 (d, 6H, j=6.1). 
     t-Butyl N-(2-fluoro-4-propoxy-3-pyridinyl) carbamate, a colorless solid melting at 84°-86° C., was obtained analogously. 
     Elemental Analysis C 13  H 19  FN 2  O 3  Calc.: %C, 57.8; %H, 7.09; %N, 10.4 Found: %C, 57.8; %H, 7.37; %N, 10.5. 
       1  H NMR (CDCl 3 ): 7.9 (d, 1H, j=5.8); 6.7 (d, 1H, j=5.8); 5.8 (br, 1H); 4.0 (t, 2H, j=6.5); 1.83 (m, 2H, j=7.36); 1.46 (s, 9H); 1.0 (t, 3H, j=7.5). 
     16. Preparation of 4-Ethoxy-2-fluoropyridine 
     To a solution of 60.5 g (0.31 mol) of 3,5-dichloro-4-ethoxy-2-fluoropyridine and 32.2 g (0.32 mol) of sodium acetate in 400 mL of ethanol in a 1 L stirred steel Parr bomb was added 3 g of 5 percent palladium on carbon catalyst. The reactor was charged with 500 pounds per square inch gauge (3550 kiloPascals) of hydrogen and heated with stirring to 100° C. for 4 hr. The mixture was cooled, filtered, and concentrated by evaporation. The residue was dissolved in ether and the resulting solution was dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue was purified by bulb to bulb distillation (60°-80° C. at 0.5 mm Hg (67 Pascals) to obtain 18.5 g (42 percent of theory) of the title compound as a colorless oil which solidified upon standing and melted at 35°-36° C. 
     Elemental Analysis C 7  H 8  NO Calc.: %C, 59.6; %H, 5.71; %N, 9.92 Found: %C, 59.2; %H, 5.97; %N, 9.95. 
       1  H NMR (CDCl 3 ): 7.9 (d, 1H, j=5.8); 6.6 (m, 1H); 6.3 (d, 1H, j=2.2); 4.0 (q, 2H, j=7.0); 1.4 (t, 3H, j=7.0). 
     2-Fluoro-4-methoxypyridine, a colorless oil boiling at 119°-122° C. at 30 mm Hg (4.0 kiloPascals), was prepared analogously. 
     Elemental Analysis C 6  H 6  FNO: Calc.: %C, 59.6; %H, 5.71; %N, 9.92 Found: %C, 59.2; %H, 5.97; %N, 9.95. 
       1  H NMR (CDCl 3 ): 8.0 (d, 1H, j=5.9); 6.7 (m, 1H); 6.4 (d, 1H, j=2.1); 3.9 (s, 3H). 
     2-Fluoro-4-(1-methylethoxy)pyridine, a colorless oil, was obtained analogously. 
     Elemental Analysis C 8  H 10  FNO Calc.: %C, 61.9; %H, 6.50; %N, 9.03 Found: %C, 61.5; %H, 6.59; %N, 9.32. 
       1  H NMR (CDCl 3 ): 8.0 (d, 1H, j=5.9); 6.6 (dd, 1H, j=4.5, 1.4); 6.33 (d, 1H, j=2.0); 4.0 (t, 2H, j=6.6); 1.8 (m, 2H, j=7.3); 1.0 (t, 3H, j=7.3). 
     2-Fluoro-4-propoxypyridine, a colorless oil, was obtained analogously. 
     Elemental Analysis C 8  H 10  FNO Calc.: %C, 61.9; %H, 6.50; %N, 9.03 Found: %C, 61.0; %H, 7.50; %N, 9.09. 
       1  H NMR (CDCl 3 ): 8.0 (d, 1H, j=5.9); 6.6 (m, 1H); 6.3 (d, 1H, j=2.2); 4.57 (m, 1H, j=6.1); 1.3 (d, 6H, j=6.1). 
     17. Preparation of 3,5-Dichloro-4-ethoxy-2-fluoropyridine 
     To a solution of 70.2 g (0.38 mol) of 3,5-dichloro-2,4-difluoropyridine in 600 mL of ethanol was slowly added with stirring a solution of sodium ethoxide in ethanol prepared from 16 g (0.40 mol) of sodium hydride (60 percent in mineral oil, hexane washed) in 200 mL of ethanol. The mixture was allowed to stir overnight and the brown solution obtained was filtered through powdered cellulose and concentrated by evaporation under reduced pressure. The residue was partitioned between 500 mL of ether and 400 mL of water. The organic phase was recovered, dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue was distilled to obtain 62 g (84 percent of theory) of the title compound as a colorless oil having a boiling point of 175°-180° C. at 0.4 mm Hg (53 Pascals). 
     Elemental Analysis C 7  H 6  Cl 2  FN Calc.: %C, 43.3; %H, 3.12; %N, 7.22 Found: %C, 40.0; %H, 2.92; %N, 6.66. 
       1  H NMR (CDCl 3 ): 8.04 (s, 1H); 4.3 (q, 2H, j=7.0); 1.48 (t, 3H, j=7.1). 
     3,5-Dichloro-2-fluoro-4-methoxypyridine, a colorless oil, was obtained analogously. 
       1  H NMR (CDCl 3 ): 8.1 (S, 1H); 4.88 (m, 1H, j=6.1); 1.4 (d, 6H, j=6.1). 
     3,5-Dichloro-2-fluoro-4-(1-methylethoxy)pyridine, a colorless oil, was obtained analogously.  1  H NMR (CDCl 3 ): 8.0 (s, 1H); 4.88 (m, 1H, j=6.1); 1.4 (d, 6H, j=6.1). 
     3,5-Dichloro-2-fluoro-4-propoxypyridine, a colorless oil, was obtained analogously.  1  H NMR (CDCl 3 ): 8.1 (s, 1H); 4.2 (t, 2H, j=6.7); 1.86 (m, 2H, j=7.1); 1.1 (t, 3H, j=7.3). 
     18. Preparation of N-(2-Chloro-4-methoxy-3-pyridinyl)-7-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide 
     To a solution of 5.4 g (33.8 mmol) of 3-amino-2-chloro-4-methoxypyridine and 3.0 g (11.3 mmol) of 2-chlorosulfonyl-7-fluoro-5-methoxy[1,2,4]triazolot1,5-c]pyrimidine in 20 mL of dry acetonitrile was added with stirring 0.91 mL (11.3 mmol) of dry pyridine and 0.16 mL (2.3 mmol) of dry dimethyl sulfoxide (DMSO). After 2 hours the resulting slurry was poured into a mixture of 200 mL of water and 800 mL of dichloromethane and the resulting mixture was stirred for 1 hour. The organic phase was recovered, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure. The residue remaining was purified by flash column chromatography to obtain 1.6 g (38 percent of theory) of the title compound as a white solid melting at 187°-188° C. 
     Elemental Analysis C 12  H 10  ClFN 6  O 4  S Calc.: %C, 37.1; %H, 2.59; %N, 21.2; %S, 8.25 Found: %C, 37.3; %H, 2.46; %N, 21.5; %S, 8.22 
       1  H NMR DMSO-d 6  : 10.7 (br, 1H), 8.2 (d, 1H, J=5.7), 7.4 (s, H), 7.1 (d, 1H, J=5.7), 4.2 (s, 3H), 3.4 (s, 3H). 
     19. Preparation of N-(2-chloro-4-methoxy-3-pyridyl)-5,7-dimethoxy[1,2,4]triazplo[1,5-c]pyrimidine-2-sulfonamide 
     To a solution of 0.60 g (1.5 mmol) of N-(2-chloro-4-methoxy-3-pyridinyl)-7-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide in 20 mL of dimethyl sulfoxide was added with stirring 0.24 g (3.4 mmol) of potassium methoxide in 2.4 mL of dry methanol. After 1 hour 5 mL of acetic acid was added and the solution taken up in 400 mL of dichloromethane. The resulting solution was washed with water (6×150 mL), dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain 270 mg (20 percent of theory) of the title compound as a white solid melting at 197°-199° C. with decomposition. 
     Elemental Analysis C 13  H 13  ClN 6  O 4  S Calc.: %C, 39.0; %H, 3.27; %N, 21.0 Found: %C, 39.0; %H, 3.40; %N, 20.9 
       1  H NMR DMSO-d 6  : 10.6 (br, 1H); 8.2 (d, 1H, J=5.7 ); 7.1 (d, 1H, J=5.7); 6.7 (s, 1H); 4.2 (s, 3H); 3.9 (s, 3H); 3.4 (s, 3H). 
     20. Preparation of N-(4-Ethoxy-3-pyridinyl)-5-methoxy-7-methyl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide 
     2-Chlorosulfonyl-5-methoxy-7-methyl[1,2,4]triazolo[1,5-c]pyrimidine (1.5 g, 5.7 mmol) was added to a solution of 0.8 g (5.7 mmol) of 3-amino-4-ethoxypyridine in 30 mL of dry pyridine in portions over 10 minutes with stirring. After 16 hours the reaction mixture was poured into 400 mL of dichloromethane. The resulting mixture was washed with 150 mL of water, dried over magnesium smlfate, and filtered. The liltrate was combined with 5 g of silica gel and the mixture was concentrated by evaporation under reduced pressure. The resulting silica plug was placed onto a 200 g silica gel column and eluted with dichloromethane containing increasing amount of ethanol. The product fractions were combined and concentrated by evaporation under reduced pressure and the solid obtained was dried to obtain 0.75 g (36 percent of theory) of the title compound as a white solid melting at 184°-186° C. 
     Elemental Analysis C 14  H 16  N 6  O 4  S Calc.: %C, 46.2; %H, 4.43; %N, 23.1; %S, 8.08 Found: %C, 46.5; %H, 4.37; %N, 22.8; %S, 7.98 
       1  H NMR (DMSO-d6): 10.5 (br, 1H); 8.3 (s, 1H); 8.26 (d, 1H, J=5.6); 7.4 (s, 1H); 7.0 (d, 1H, J=5.6); 4.2 (s, 3H); 3.9 (q, 2H, J=7.0); 2.5 (s, 1H); 1.0 (t, 3H, J=7.0). 
     21. Evaluation of Postemergence Herbicidal Activity 
     Seeds of the desired test plant species were planted in Grace-Sierra MetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic pots with a surface area of 64 square centimeters. When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 7-21 days in a greenhouse with an approximately 15 hr photoperiod which was maintained at about 23°-29° C. during the day and 22°-28° C. during the night. Nutrients and water were added on a regular basis and supplemental lighting was provided with overhead metal halide 1000 Watt lamps as necessary. The plants were employed for testing when they reached the first or second true leaf stage. 
     A weighed amount, determined by the highest rate to be tested, of each test compound was placed in a 20 mL glass vial and was dissolved in 4 mL of a 97:3 v/v (volume/volume) mixture of acetone and dimethyl sulfoxide to obtain concentrated stock solutions. If the test compound did not dissolve readily, the mixture was warmed and/or sonicated. The concentrated stock solutions obtained were diluted with an aqueous mixture containing acetone, water, isopropyl alcohol, dimethyl sulfoxide, Atplus 411F crop oil concentrate, and Triton X-155 surfactant in a 48.5:39:10:1.5:1.0:0.02 v/v ratio to obtain spray solutions of known concentration. The solutions containing the highest concentration to be tested were prepared by diluting 2 mL aliquots of the stock solution with 13 mL of the mixture and lower concentrations were prepared by dilution of appropriate smaller portions of the stock solution. Approximately 1.5 mL aliquots of each solution of known concentration were sprayed evenly onto each of the test plant pots using a DeVilbiss atomizer driven by compressed air pressure of 2 to 4 psi (140 to 280 kiloPascals) to obtain thorough coverage of each plant. Control plants were sprayed in the same manner with the aqueous mixture. In this test an application rate of 1 ppm results in the application of approximately 1 g/Ha. 
     The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After 2 weeks the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill. Some of the compounds tested, application rates employed, plant species tested, and results are given in Tables 2 and 2A. 
     
                                           TABLE 2__________________________________________________________________________POSTEMERGENCE HERBICIDAL ACTIVITY                          WildCpd.   Rate,  Cockle-       Jimson-            Morning-                 Velvet-                      Field                          Buck-                              Black-                                  Giant                                      Johnson-No.   ppm bur  weed glory                 leaf Pansy                          wheat                              grass                                  foxtail                                      grass__________________________________________________________________________ 1 1000  15   85   15   65   --  30  55  0   15 2 250 55   40   70   40   50  70  35  0   0 3 125 90   85   90   100  89  85  85  90  70 4 250 100  100  85   88   80  88  75  30  60 5 250 90   80   85   95   90  85  80  85  75 6 2000  80   85   0    85   30  80  50  60  15 7 1000  80   50   85   85   80  88  50  80  20 8 31.3  90   --   95   98   100 85  80  78  70 9 250 90   --   75   85   100 90  80  80  7810 125 90   80   70   85   70  75  80  40  9011 2000  75   80   75   70   98  70  80  78  7512 1000  80   90   90   75   90  80  98  75  9013 7.81  100  90   50   80   98  90  70  70  8014 15.6  99   83   100  100  0   85  75  20  9515 7.81  90   88   85   75   70  75  60  60  8516 15.6  100  --   90   90   70  85  70  80  9017 62.5  85   90   85   95   70  90  70  30  6018 15.6  80   --   80   80   60  80  75  50  7519 7.81  85   --   100  80   40  80  60  50  7820 7.81  98   --   95   80   0   80  40  0   7521 7.81  90   70   70   98   70  70  60  20  8522 15.6  85   85   75   75   45  80  40  40  6023 15.6  98   80   80   90   80  90  80  35  --24 15.6  100  80   100  50   70  90  70  80  9025 31.3  100  95   85   100  70  100 78  60  9026 15.6  98   100  85   90   20  100 70  40  027 31.3  80   80   80   80   0   80  0   0   4528 500 15   80   70   80   70  70  85  80  9029 15.6  100  93   75   65   80  95  45  40  8330 31.3  75   80   70   98   70  75  95  10  10031 500 80   80   70   80   90  75  85  75  8532 125 90   80   70   85   40  80  8 o 45  7533 125 70   80   80   80   85  85  75  30  4034 15.6  99   80   80   80   100 98  20  45  8035 31.3  90   85   88   85   88  85  90  85  8836 125 70   88   90   85   100 86  90  85  8437 62.5  85   90   90   89   100 80  89  85  8538 15.6  88   80   85   88   75  88  75  80  8039 250 75   70   85   95   95  95  90  90  9040 81  83   95   70   83   100 75  60  40  7541 31.3  70   80   85   93   70  93  80  20  8342 31.3  100  70   75   80   100 100 70  70  8543 125 85   80   88   100  75  85  50  50  8544 500 50   75   85   85   50  85  70  20  7545 31.3  --   --   90   88   70  80  50  85  9046 31.3  --   --   88   88   88  88  75  70  9547 62.5  75   80   85   80   80  78  80  65  8048 7.81  90   0    85   80   80  80  70  70  9049 15.6  100  88   88   80   80  80  40  40  8550 15.6  100  88   90   85   70  84  35  30  8551 31.3  90   90   88   88   90  80  88  90  8052 15.6  90   --   85   70   75  85  55  70  8553 15.6  90   --   88   85   88  88  55  70  10054 500 90   --   90   85   85  90  70  70  8555 250 95   98   90   80   80  90  0   40  6056 62.5  90   80   80   75   80  75  65  20  7057 31.3  20   80   40   85   70  75  90  70  8558 500 60   80   60   80   95  80  80  80  8059 62.5  40   80   60   80   90  80  75  70  9060 500 85   75   80   88   90  70  80  90  7561 62.5  60   85   80   85   95  90  90  90  9063 15.6  70   70   80   90   85  85  90  40  8864 500 100  95   75   85   85  85  65  50  8565 250 100  95   90   80   80  75  60  60  6066 250 100  90   85   75   98  85  60  60  3067 1000  99   70   45   40   85  75  45  10  6068 1000  100  80   90   75   83  93  70  45  8069 62.5  97   55   70   95   99  90  45  70  770 1000  77   83   95   75   70  70  80  65  2071 500 100  90   95   85   83  50  50  65  072 62.5  100  80   100  90   90  85  0   70  10073 31.3  98   75   80   75   90  80  75  60  9074 1000  85   75   80   80   85  83  75  70  9975 250 100  75   75   90   90  80  85  100 7576 1000  80   75   85   50   40  70  70  75  60__________________________________________________________________________ 
    
     
                                           TABLE 2A__________________________________________________________________________POSTEMERGENCE HERBICIDAL ACTIVITY                          Wild        ROXCpd.   Rate,  Cockle-       Lambs-            Morning-                 Velvet-                      Field                          Buck-                              Black-                                  Giant                                      OrangeNo.   ppm bur  quarter            glory                 leaf Pansy                          wheat                              grass                                  foxtail                                      Sorghum__________________________________________________________________________ 77   500 98   60   75   75   90  65  70  75  78 78   62.5  100  60   100  100  75  80  90  80  90 79   31.3  100  55   88   85   55  87  70  75  75 80   15.6  100  90   85   85   87  88  90  85  8 81   1.95  88   80   85   85   90  80  85  70  70 82   15.6  90   60   90   85   88  80  85  30  75 83   62.5  90   90   80   --   70  --  75  85  70 84   500 78   65   75   60   80  50  75  85  70 85   2 50  90   90   80   70   60  78  80  80  85 86   500 88   60   90   70   80  70  70  75  90 87   62.5  100  80   85   80   80  80  60  70  85 88   62.5  90   60   100  75   80  85  35  40  85 89   15.6  100  75   90   90   80  75  40  40  78 90   250 100  85   90   90   75  88  90  80  100 91   125 100  85   85   80   80  80  85  75  88 92   125 100  85   78   90   75  85  85  50  78 93   31.3  95   60   85   85   75  80  80  45  80 95   125 100  65   80   75   60  70  70  70  65 96   7.8 100  50   98   70   60  70  40  20  70 97   500 100  80   85   85   40  85  70  60  40 98   250 100  60   80   80   70  80  50  20  80 99   250 90   50   85   85   85  85  80  85  90100   62.5  90   90   85   90   90  95  90  95  95101   15.6  100  70   80   80   60  70  90  70  80102   125 100  50   80   70   50  80  30  80  70103   500 100  65   80   70   70  80  85  80  85104   62.5  100  60   90   90   75  70  90  30  85105   62.5  80   20   90   60   70  70  65  60  98107   31.3  70   70   80   75   70  70  95  95  98108   1.3 100  70   98   98   70  80  65  30  80110   250 90   70   90   65   80  90  80  75  80112   125 98   --   85   85   90  80  90  50  95113   500 85   --   80   70   70  50  75  30  80114   250 100  --   80   80   70  85  75  20  75115   62.5  85   100  80   90   90  90  98  50  90116   62.5  100  --   90   75   80  80  80  60  80117   31.2  90   100  90   80   90  80  90  35  90118   15.6  100  --   80   75   85  80  80  30  90119   15.6  90   --   80   85   90  85  90  30  90120   15.6  95   --   80   90   95  85  85  90  90121   31.2  85   --   75   80   95  70  75  0   8122   62.5  90   --   80   75   85  75  80  50  90123   7.8 100  --   75   90   90  80  80  70  85124   15.6  85   --   85   85   90  90  88  90  95125   500 100  70   90   75   78  80  80  50  90126   125 100  90   75   80   80  70  75  55  85127   3.9 98   90   95   85   80  60  80  65  75128   3.9 100  78   90   78   83  70  85  0   75129   7.8 99   80   90   78   75  95  98  0   75130   15.6  100  78   100  83   75  95  85  5   65131   15.6  100  85   90   98   75  80  95  70  90132   62.5  100  78   100  93   80  80  85  65  88133   15.6  98   90   95   98   83  83  83  65  78134   15.6  95   78   88   98   75  93  95  55  78135   62.5  100  88   75   93   65  95  98  65  78136   15.6  100  88   100  78   75  95  98  20  75137   15.6  100  --   80   99   65  83  90  65  95138   31.2  100  --   98   75   88  98  95  40  95139   31.2  100  --   98   80   75  95  98  50  70140   125 100  --   99   80   80  98  98  70  78141   15.6  100  --   80   95   75  98  99  20  93142   15.6  98   80   80   78   70  83  99  70  85143   15.6  98   --   100  85   78  88  98  75  95144   31.2  100  --   85   85   78  75  98  65  75145   62.5  100  --   90   0    95  80  60  70  90146   62.5  100  --   90   70   80  80  50  50  90147   3.9 99   80   75   95   75  90  70  78  88148   1.95  95   98   95   98   60  83  78  65  93149   15.6  100  99   78   78   178 78  90  55  80150   15.6  100  100  100  98   80  78  98  60  78151   7.8 100  98   100  78   75  80  95  50  78152   31.2  98   85   98   85   78  70  98  5   83153   15.6  100  95   90   80   78  --  70  50  78154   15.6  100  95   95   80   78  90  70  75  78155   62.5  100  --   98   98   85  98  93  70  85156   15.6  100  --   95   98   75  95  90  10  65157   31.2  100  --   78   90   70  70  98  70  70158   31.2  90   --   70   70   78  80  98  75  85159   15.6  98   --   98   75   60  75  95  50  83160   15.6  100  --   98   75   50  75  93  0   90161   31.2  100  --   98   85   70  80  95  65  80162   15.6  100  --   100  78   80  78  98  60  80163   31.2  90   --   90   70   75  78  80  25  70164   31.2  99   --   70   70   78  70  95  25  65165   15.6  95   90   85   70   85  85  80  20  80166   15.6  100  88   90   90   85  90  80  90  90167   15.6  100  100  100  90   85  90  88  80  88168   9.8 98   78   100  95   90  80  78  70  78169   15.6  100  75   90   90   85  90  90  70  78170   31.2  100  95   75   80   88  80  80  80  90__________________________________________________________________________ 
    
     22. Evaluation of Preemergence Herbicidal Activity 
     Seeds of the desired test plant species were planted in a soil matrix prepared by mixing a loam soil which was composed of about 43 percent silt, 19 percent clay, and 38 percent sand and had a pH of about 8.1 and an organic matter content of about 1.5 percent and sand in a 70 to 30 ratio. The soil matrix was contained in plastic pots with a surface area of 161 square centimeters. When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. 
     A weighed amount, determined by the highest rate to be tested, of each test compound was placed in a 20 mL glass vial and was dissolved in 8 mL of a 97:3 v/v (volume/volume) mixture of acetone and dimethyl sulfoxide to obtain concentrated stock solutions. If the test compound did not dissolve readily, the mixture was warmed and/or sonicated. The stock solutions obtained were diluted with a 99.9:0.1 mixture of water and Tween® 155 surfactant to obtain application solutions of known concentration. The solutions containing the highest concentration to be tested were prepared by diluting 4 mL aliquots of the stock solution with 8.5 mL of the mixture and lower concentrations were prepared by dilution of appropriate smaller portions of the stock solution. A 2.5 mL aliquot of each solution of known concentration was sprayed evenly onto the soil of each seeded pot using a Cornwall 5.0 mL glass syringe fitted with a TeeJet TN-3 hollow cone nozzle to obtain thorough coverage of the soil in each pot. Control pots were sprayed in the same manner with the aqueous mixture. A highest application rate of 4.48 Kg/Ha is achieved when 50 mg of test compound is employed. 
     The treated pots and control pots were placed in a greenhouse with an approximately 15 hr photoperiod which was maintained at about 23°-29° C. during the day and 22°-28° C. during the night. Nutrients and water were added on a regular basis and supplemental lighting was provided with overhead metal halide 1000 Watt lamps as necessary. The water was added by top-irrigation. After 3 weeks the condition of the test plants that germinated and grew as compared with that of the untreated plants that germinated and grew was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill or no germination. Some of the compounds tested, application rates employed, plant species tested, and results are given in Table 3. 
     
                                           TABLE 3__________________________________________________________________________PREEMERGENCE HERBICIDAL ACTIVITY                 Wild    Barn-Cpd.   Rate,  Morning-  Velvet-                 Buck-                     Black                         yard                             Giant                                 Johnson-No.   Kg/Ha  glory       Pigweed            leaf wheat                     grass                         Grass                             foxtail                                 grass__________________________________________________________________________2  1.12  40   50   75   60  70  603  0.56  85   80   80   80  70  90  95  204  1.12  90   100  85   98  10  95  75  755  2.24  60   75   85   85  25  98  98  208  0.56  50   90   80   90  90  90  98  509  1.12  8    95   85   90  8   98  98  9010 1.12  85   90   95   90  98  5   75  --11 4.48  50   100  98   30  100 100 60  10013 0.035  90   100  95   --  90  65  90  9014 0.14  80   98   95   90  85  95  80  --15 0.14  90   85   90   90  5   90  90  9016 0.018  40   100  90   100 80  90  80  --17 0.035  80   98   95   50  70  90  20  --18 0.035  80   95   80   50  90  95  30  --19 0.018  80   90   90   0   50  80  60  --20 0.035  90   90   80   80  80  95  50  --21 0.018  80   98   80   70  60  95  60  --22 0.035  90   85   95   80  70  85  20  --23 0.14  80   90   95   90  30  0   60  6024 0.070  90   100  70   90  90  98  100 9025 0.070  60   100  80   75  60  98  20  8526 0.035  90   100  85   5   90  90  60  8027 0.035  60   100  95   90  95  98  80  8028 0.056  50   98   98   80  98  98  98  7529 0.070  80   90   80   85  75  100 75  9030 0.14  95   90   95   85  98  98  50  9831 1.12  50   75   50   30  75  75  50  7532 0.56  98   98   85   90  98  98  50  9833 0.28  90   95   10   95  75  60  40  8034 0.070  75   100  90   90  50  50  70  8035 0.070  80   95   85   80  100 70  90  9036 0.28  5    60   85   90  100 98  90  9037 0.018  80   80   75   90  90  98  80  8538 0.035  90   98   95   98  90  85  95  9839 0.035  40   90   85   98  80  90  85  9040 0.018  90   100  90   --  40  60  75  9041 0.28  90   100  98   --  95  90  95  9042 0.035  90   100  95   --  50  40  60  9043 0.56  90   30   75   90  95  98  60  9045 0.035  70   98   80   88  40  70  85  8546 0.28  40   90   60   70  o   60  65  8547 0.14  40   90   80   87  95  75  Po  8048 0.009  60   95   70   75  80  90  70  9049 0.070  90   98   85   95  75  90  78  9050 0.14  90   98   5    95  65  98  65  9051 0.070  88   90   90   80  95  80  85  8852 0.035  90   97   75   90  65  80  70  9053 0.009  90   85   85   88  85  90  75  8854 0.14  90   85   85   90  60  70  45  8055 0.56  90   90   65   90  70  65  30  8056 0.28  5    80   75   80  40  40  30  6557 0.56  75   80   85   50  80  55  80  9058 1.12  65   95   80   55  95  70  75  9059 0.14  75   90   90   90  75  70  0   9060 1.12  100  90   65   70  98  80  65  8061 0.14  90   98   88   90  10  70  90  8063 0.14  70   90   85   90  95  95  80  9564 1.12  80   80   70   80  98  60  75  9565 0.56  80   60   70   50  99  80  80  9066 0.56  90   70   60   70  90  90  90  7067 0.28  20   70   30   65  90  70  30  8068 0.28  65   80   50   85  100 90  80  9069 0.070  85   90   75   90  60  70  70  7570 1.12  30   50   40   20  30  85  95  5071 2.24  75   90   50   40  50  90  70  6072 0.070  50   90   50   60  50  50  60  9073 0.035  70   70   70   80  85  95  90  9074 1.12  60   90   50   50  50  70  50  9075 0.56  80   95   80   90  80  85  95  5077 0.28  40   50   50   --  70  70  90  --78 0.070  85   95   95   --  95  98  90  --79 0.28  85   75   90   --  85  85  95  --80 0.070  80   85   98   --  98  20  95  --81 0.070  90   90   90   --  95  80  85  --82 0.28  95   50   80   --  100 95  60  --83 0.28  90   80   70   --  85  95  60  --84 2.24  85   90   65   --  90  65  70  --85 1.12  75   50   75   --  80  75  60  --87 0.070  80   60   85   --  80  95  85  --88 0.14  80   80   90   --  80  95  80  --89 0.14  85   75   85   --  85  90  80  --90 0.070  90   90   95   --  95  85  70  --91 0.070  85   85   90   --  95  90  95  --92 0.56  75   80   90   --  95  95  75  --93 0.14  85   75   90   --  98  95  25  --94 0.28  60   40   25   --  70  75  70  --97 1.12  90   85   70   --  60  70  50  --98 1.12  78   90   85   --  65  80  75  --101   0.035  85   80   85   --  85  85  75  --102   0.28  35   70   80   --  90  95  80  --103   0.28  35   65   80   --  85  85  60  --104   0.070  85   80   95   --  95  75  50  --105   0.14  90   90   85   --  90  70  75  --108   0.14  90   74   95   --  85  90  75  --110   0.56  60   70   78   --  90  100 95  --112   0.14  80   95   85   --  --  100 78  --113   1.12  20   95   90   --  --  60  50  --114   1.12  90   95   80   --  --  78  55  --115   0.28  90   85   85   --  --  98  90  --116   0.28  90   70   90   --  --  80  60  --117   0.28  85   95   90   --  --  95  90  --118   0.14  90   70   80   --  --  60  70  --119   0.070  90   95   95   --  --  70  85  --120   0.070  90   98   95   --  --  80  90  --121   1.12  90   100  80   --  --  98  78  --122   0.56  90   55   85   --  95  80  75  --123   0.14  90   80   90   --  --  95  95  --124   0.14  90   95   95   --  --  90  80  --125   0.56  85   90   80   --  --  85  70  --126   0.28  85   95   90   --  --  78  78  --127   0.14  85   95   90   --  80  95  90  --128   0.007  85   70   80   --  100 95  90  --129   0.14  85   98   90   --  90  95  95  --130   0.14  85   95   90   --  98  80  80  --131   0.14  85   98   85   --  100 95  95  --132   0.14  95   80   85   --  90  90  78  --133   0.14  95   80   85   --  90  90  78  --134   0.070  90   70   85   --  90  95  70  --135   0.14  90   75   90   --  90  70  50  --136   0.070  90   70   85   --  95  70  50  --137   0.035  80   100  80   --  80  95  78  --138   0.14  80   100  85   --  90  78  70  --139   0.14  90   70   90   --  90  90  90  --140   0.28  90   70   90   --  95  85  75  --141   0.035  90   80   80   --  78  90  65  --142   0.14  90   90   90   --  90  90  90  --143   0.14  90   78   80   --  95  90  90  --144   0.14  90   78   80   --  99  85  75  --145   0.14  60   100  78   --  60  90  85  --146   0.28  80   90   80   --  70  95  80  --147   0.035  90   85   90   --  80  95  85  --148   0.035  90   90   90   --  80  100 95  --149   0.070  90   85   80   --  90  85  80  --150   0.14  90   80   90   --  90  100 90  --151   0.070  90   90   90   --  90  85  80  --152   0.14  90   78   90   --  98  90  78  --153   0.070  80   95   80   --  78  95  90  --154   0.14  90   90   80   --  85  100 95  --155   0.070  85   100  85   --  90  98  75  --156   0.070  85   95   90   --  75  90  70  --157   0.14  90   90   90   --  95  50  75  --158   0.28  85   95   90   --  90  70  90  --159   0.14  90   100  90   --  90  80  70  --160   0.14  90   95   85   --  85  90  60  --161   0.14  90   90   85   --  90  80  70  --162   0.070  80   90   90   --  90  60  40  --163   0.56  90   80   90   --  95  80  80  --164   0.28  90   50   85   --  95  80  60  --165   0.070  90   95   95   --  90  80  90  --166   0.070  90   80   95   --  85  85  80  --167   0.035  90   80   90   --  80  95  95  --168   0.035  90   85   98   --  90  99  90  --169   0.018  90   75   90   --  85  100 75  --170   0.14  80   98   75   --  85  98  90  --__________________________________________________________________________